JP7845876B2 - Method for producing β-lysophospholipids, and their uses - Google Patents

Description

This invention relates to a method for producing β-lysophospholipids, and to cosmetics or topical skin preparations containing β-lysophospholipids.

Lysophospholipids are generally a group of compounds having a structure in which fatty acids are ester-bonded to the sn-1 and sn-2 positions of a glycerol skeleton, and a polar group containing phosphate is bonded to the sn-3 position. Depending on the structure of the polar group, lysophosphatidylcholine (LPC), lysophosphatidylethanolamine (LPE), lysophosphatidylserine (LPS), lysophosphatidylinositol (LPI), and lysophosphatidic acid (LPA) are known. As for lysophospholipids, the α-type, in which a polar group containing phosphate is bonded to the sn-3 position as described above, is common, but the β-type, in which a polar group containing phosphate is bonded to the sn-2 position, is also known to exist. However, there has been little research on β-type lysophospholipids. Non-patent document 1 describes the production of β-type lysophosphatidic acid (β-LPA) when cyclic phosphatidic acid (cPA) is reacted with the phospholipid metabolic enzyme autotaxin (ATX). However, there is currently no information available on how to industrially produce β-lysophosphatidic acid, nor are there any known applications for it.

Scientific Reports 11 17360 (2021)

The object of this invention is to provide a new industrially applicable method for producing β-lysophosphatidic acid. Another object of this invention is to provide new applications for β-lysophosphatidic acid.

The inventors of the present invention conducted extensive research to solve the above problems and found that the aforementioned problems can be solved by a manufacturing method including the following steps (1) to (3), thereby completing the present invention.
(1) A step of reacting lecithin containing phosphatidylcholine with phospholipase A2 in water or a mixture of water and an organic solvent. (2) A step of reacting the product obtained in step (1) with phospholipase D in water or a mixture of water and an organic solvent. (3) A step of hydrolyzing the product obtained in step (2) in water or a mixture of water and an organic solvent under acidic conditions.

The manufacturing method of the present invention makes it possible to industrially produce β-lysophosphatidic acid. Furthermore, since the β-lysophosphatidic acid obtained by the manufacturing method of the present invention possesses various physiologically active properties, it is preferably used in cosmetics or topical skin preparations.

The present invention relates to a method for producing β-lysophosphatidic acid, and in the present invention, β-lysophosphatidic acid is a compound represented by the following general formula (1).
(In the formula, R represents a saturated or unsaturated aliphatic acyl group having 14 to 24 carbon atoms.)

The saturated or unsaturated aliphatic acyl group with 14 to 24 carbon atoms in R of the general formula (1) is specifically a residue derived from saturated fatty acids such as myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, and lignoceric acid; or from unsaturated fatty acids such as myristoleic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid, arachidonic acid, eicosapentaenoic acid, erucic acid, and docosahexaenoic acid. Preferably, it is a residue derived from palmitic acid, stearic acid, oleic acid, linoleic acid, or linolenic acid.

The method for producing the compound represented by the general formula (1) of the present invention includes the following steps (1) to (3).
(1) A step of reacting lecithin containing phosphatidylcholine with phospholipase A2 in water or a mixture of water and an organic solvent. (2) A step of reacting the product obtained in step (1) with phospholipase D in water or a mixture of water and an organic solvent. (3) A step of hydrolyzing the product obtained in step (2) in water or a mixture of water and an organic solvent under acidic conditions.

Regarding step (1), the lecithin containing phosphatidylcholine used in step (1) of the manufacturing method of the present invention includes lecithin obtained from soybeans, rapeseed, sunflower, safflower, peanuts, cottonseed, corn, rice, barley, egg yolk, etc., or lecithin obtained by purifying these to increase the phosphatidylcholine content. Of these, lecithin derived from soybeans or sunflowers is preferred from the viewpoint of availability. These lecithins may also be hydrogenated.

The organic solvent used in step (1) of the manufacturing method of the present invention is not particularly limited, but a water-immiscible organic solvent capable of dissolving lecithin is preferably used. Specifically, examples include ethyl acetate, isopropyl acetate, butyl acetate, hexane, heptane, cyclohexane, methyl ethyl ketone, methyl isobutyl ketone, ethyl ether, toluene, and chloroform.

In step (1) of the manufacturing method of the present invention, the conditions for reacting phospholipase A2 can be any known conditions under which the enzymatic activity of phospholipase A2 is expressed. Specifically, the reaction is carried out under stirring at a temperature of 30 to 70°C, preferably 35 to 60°C, with the pH adjusted to 5 to 9, preferably 6 to 8, using a buffer solution, for 1 to 72 hours, preferably 5 to 48 hours.

In step (1) of the manufacturing method of the present invention, phosphatidylcholine contained in lecithin is lyzated and converted to lysophosphatidylcholine. Therefore, the product obtained in step (1) contains lysophosphatidylcholine. Depending on the type of lecithin used as a raw material, the product obtained in step (1) may contain, in addition to lysophosphatidylcholine, lysophospholipids such as lysophosphatidic acid, lysophosphatidylethanolamine, lysophosphatidylserine, and lysophosphatidylinositol, as well as unlyzated phospholipids such as phosphatidylcholine, phosphatidic acid, phosphatidylethanolamine, phosphatidylserine, and phosphatidylinositol. However, in the present invention, the product may contain such various components derived from lecithin. The product obtained in step (1) can be used directly in step (2), but it may also be purified by general methods such as extraction and reprecipitation.

Regarding step (2) , there are no particular restrictions on the organic solvent used in step (2) of the manufacturing method of the present invention, but it is preferable to use a water-immiscible organic solvent that can dissolve the product obtained in step (1). Specifically, examples include ethyl acetate, isopropyl acetate, butyl acetate, hexane, heptane, cyclohexane, methyl ethyl ketone, methyl isobutyl ketone, ethyl ether, toluene, and chloroform.

In step (2) of the manufacturing method of the present invention, the conditions for reacting with phospholipase D can be any known conditions under which the enzymatic activity of phospholipase D is expressed. Specifically, the reaction is carried out under stirring at a temperature of 25 to 60°C, preferably 30 to 55°C, with the pH adjusted to 4 to 8, preferably 5 to 7, using a buffer solution, and for 1 to 72 hours, preferably 5 to 48 hours.

In step (2) of the manufacturing method of the present invention, the lysophosphatidylcholine contained in the product of step (1) is converted to cyclic phosphatidic acid; therefore, the product obtained in step (2) contains cyclic phosphatidic acid. The product obtained in step (2) may contain unreacted lysophosphatidylcholine and various components derived from lecithin as described above, in addition to cyclic phosphatidic acid; however, the present invention may use products containing such components. The product obtained in step (2) can be used directly in step (3), but it may also be purified by general methods such as extraction and reprecipitation.

Regarding step (3) , in addition to the water-immiscible organic solvent used in step (1) or (2) above, water-miscible organic solvents can also be used as the organic solvent used in step (3) of the manufacturing method of the present invention. Specifically, examples include ethanol, propanol, isopropanol, glycerin, propylene glycol, 1,3-butylene glycol, and acetone.

In step (3) of the manufacturing method of the present invention, "acidic conditions" means adding an acidic component such as hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, or citric acid to achieve an acidity sufficient for hydrolysis to proceed. There are no particular restrictions, but generally, the pH should be 3 or lower, preferably 2 or lower. Hydrolysis should be carried out while heating at 20 to 90°C, preferably 40 to 80°C.

In step (3) of the manufacturing method of the present invention, the cyclic phosphate group of the cyclic phosphatidic acid contained in the product of step (2) undergoes ring-opening by hydrolysis, generating the desired β-lysophosphatidic acid represented by general formula (1). In step (3), hydrolysis of the cyclic phosphatidic acid also generates α-lysophosphatidic acid in roughly the same proportion as β-lysophosphatidic acid. Therefore, the product obtained in step (3) may contain α-lysophosphatidic acid in addition to β-lysophosphatidic acid, and may also contain various components derived from lecithin as described above; however, the present invention may contain such components. The product obtained in step (3) can be used directly for its intended purpose, but it may also be purified by general methods such as extraction and reprecipitation.

The product obtained in step (3) contains the β-lysophosphatidic acid of the present invention, and the content of β-lysophosphatidic acid can be measured using HPLC under the following conditions.

Column: CAPCELL PAK NH2 (4.6 mm I.D. x 250 mm)
Detector: UV (205 nm)
Temperature: 40℃
Mobile phase: Acetonitrile/methanol/10 mM ammonium phosphate solution/phosphoric acid
= 620/290/90/1
Flow rate: 1.3mL/min

The β-lysophosphatidic acid of the present invention, obtained by the above manufacturing method, possesses various physiologically active properties and can therefore be preferably used in cosmetics or topical skin preparations. There are no particular restrictions on the amount of the lysophosphatidic acid of the present invention incorporated into cosmetics or topical skin preparations; typically, it is incorporated at 0.005 to 20% by weight, preferably 0.01 to 10% by weight.

The β-lysophosphatidic acid of the present invention may also be in the form of a salt. While there are no particular limitations on the salt, specific examples include alkali metal salts such as sodium and potassium; alkaline earth metal salts such as calcium and magnesium; metal salts such as aluminum, iron, and zinc; basic amino acid salts such as lysine, arginine, guanidine, histidine, and ornithine; and organic amine salts such as ammonium, monoethanolamine, diethanolamine, triethanolamine, tromethamine, and stearylamine. The β-lysophosphatidic acid of the present invention can exert its effects in either the form of an acid or a salt. From the viewpoint of irritancy, aluminum and zinc are preferred.

The cosmetic or topical skin preparation of the present invention may optionally contain water and additives commonly used in cosmetics, such as oily bases, moisturizers/texture enhancers, surfactants, polymers/thickeners/gelling agents, antioxidants, reducing agents, oxidizing agents, antioxidants, whitening agents, vitamins and their derivatives, plant/animal/microbial extracts, UV absorbers, antibacterial/preservatives, chelating agents, pH adjusters/acids/alkalis, solvents/propellants, antipruritics, exfoliating/dissolving agents, antiperspirants, cooling agents, astringents, enzymes, nucleic acids, anti-inflammatory agents, hair growth agents/blood circulation promoters/stimulants, hormones, anti-wrinkle/anti-aging agents, irritation relievers, cooling agents, warming agents, powders, pigments/colorants/dyes/pigments, fragrances, etc., in amounts that do not impair the effects of the present invention.

As oily bases, higher alcohols such as cetanol, myristyl alcohol, oleyl alcohol, lauryl alcohol, cetostearyl alcohol, stearyl alcohol, arachidodecanol, behenyl alcohol, jojoba alcohol, chymyl alcohol, cerachidodecanol, batyl alcohol, hexyldecanol, isostearyl alcohol, 2-octyldodecanol, and dimergol; aralkyl alcohols and derivatives such as benzyl alcohol; lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, behenic acid, undecylenic acid, and 12-hydroxyl Higher fatty acids such as cystearic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid, erucic acid, docosahexaenoic acid, eicosapentaenoic acid, isohexadecanoic acid, anteisohenicosanoic acid, long-chain branched fatty acids, long-chain α-hydroxy fatty acids, dimer acids, hydrogenated dimer acids, and other higher fatty acids, as well as metal soaps such as aluminum salts, calcium salts, magnesium salts, zinc salts, potassium salts, and sodium salts thereof, and nitrogen-containing derivatives such as amides; liquid paraffin (mineral oil), heavy liquid isoparaffin, light liquid isoparaffin, α-olefin oligomers, polyisobutene, hydrogenated polyisobutene Hydrocarbons such as cellulose, polybutene, squalane, olive-derived squalane, squalene, petrolatum, and solid paraffin; waxes such as candelilla wax, carnauba wax, rice wax, wood wax, beeswax, montan wax, ozokerite, ceresin, paraffin wax, microcrystalline wax, petrolatum, Fischer-Tropsch wax, polyethylene wax, and ethylene-propylene copolymer; coconut oil, palm oil, palm kernel oil, safflower oil, olive oil, castor oil, avocado oil, sesame oil, tea oil, evening primrose oil, wheat germ oil, macadamia nut oil, hazelnut oil Vegetable oils such as nut oil, kukui nut oil, rosehip oil, meadowfoam oil, peach kernel oil, tea tree oil, peppermint oil, corn oil, rapeseed oil, sunflower oil, wheat germ oil, linseed oil, cottonseed oil, soybean oil, peanut oil, rice bran oil, cocoa butter, shea butter, hydrogenated coconut oil, hydrogenated castor oil, jojoba oil, hydrogenated jojoba oil, etc.; animal fats such as beef tallow, milk fat, horse fat, egg yolk oil, mink oil, turtle oil, etc.; animal waxes such as whale wax, lanolin, orange roughy oil, etc.; liquid lanolin, reduced lanolin, adsorbed and refined lanolin, lanolin acetate, liquid lanolin acetate, hydroxylanolin, polyoxyethylene lanolin Lanolins such as lanolin fatty acid, hard lanolin fatty acid, lanolin alcohol, lanolin acetate alcohol, and (cetyl lanolyl) acetate; sphingophospholipids such as lecithin, phosphatidylcholine, phosphatidylethanolamine, phosphatidylserine, phosphatidylglycerol, phosphatidylinositol, and sphingomyelin; phospholipids such as phosphatidic acid, cyclic lysophosphatidic acid or its salts, and lysolecithin; phospholipid derivatives such as hydrogenated soybean phospholipid, partially hydrogenated soybean phospholipid, hydrogenated egg yolk phospholipid, and partially hydrogenated egg yolk phospholipid; cholesterol , dihydrocholesterol, lanosterol, dihydrolanosterol, phytosterol, cholic acid and other sterols; sapogenins; saponins; cholesteryl acetate, cholesteryl nonanoate, cholesteryl stearate, cholesteryl isostearate, cholesteryl oleate, N-lauroyl-L-glutamic acid di(cholesteryl/behenyl/octyldodecyl), N-lauroyl-L-glutamic acid di(cholesteryl/octyldodecyl), N-lauroyl-L-glutamic acid di(phytosteryl/behenyl/octyldodecyl), N-lauroyl-L-glutamic acid di(phytos Sterol esters such as teryl/octyldodecyl, N-lauroyl sarcosinate isopropyl, 12-hydroxystearate cholesteryl, macadamia nut oil fatty acid cholesteryl, macadamia nut oil fatty acid phytosteryl, sunflower seed oil fatty acid phytosteryl, isostearate phytosteryl, soft lanolin fatty acid cholesteryl, hard lanolin fatty acid cholesteryl, long-chain branched fatty acid cholesteryl, long-chain α-hydroxy fatty acid cholesteryl; lipid complexes such as phospholipid-cholesterol complexes and phospholipid-phytosterol complexes; myris Octyldodecyl tinate, hexyldecyl myristate, octyldodecyl isostearate, cetyl palimitate, octyldodecyl palmitate, cetyl octanoate, hexyldecyl octanoate, isotridecyl isononanoate, isononyl isononanoate, octyl isononanoate, isotridecyl isononanoate, isodecyl neopentanoate, isotridecyl neopentanoate, isostearyl neopentanoate, octyldodecyl neodecanoate, oleyl oleate, octyldodecyl oleate, octyldodecyl ricinoleate, octyldodecyl lanolate, dicaprylyl carbonate, dimethyl Hexyldecyl octanoate, octyldodecyl erucate, hydrogenated castor oil isostearate, ethyl oleate, ethyl avocado oil fatty acid, isopropyl myristate, isopropyl palmitate, octyl palmitate, isopropyl isostearate, isopropyl lanolinate, methylheptyl laurate, methylheptyl myristate, methylheptyl palmitate, methylheptyl isostearate, diethyl sebacate, diisopropyl sebacate, dioctyl sebacate, diisopropyl adipate, dibutyloctyl sebacate, diisobutyl adipate, diisobutyl succinate Octyl, triethyl citrate and other monoalcoholic carboxylic acid esters; cetyl lactate, hydrogenated castor oil monoisostearate, γ-ercalactone, diisostearyl malate and other oxyacid esters; glyceryl trioctanoate, glyceryl trioleate, glyceryl triisostearate, glyceryl diisostearate, caprylic/capric triglyceride, caprylic/capric/myristic/stearic triglyceride, hydrogenated rosin triglyceride (hydrogenated ester gum), rosin triglyceride (ester gum), glyceryl eicosanedioate behenate, Trimethylolpropane rioctanoate, trimethylolpropane triisostearate, neopentyl glycol dioctanoate, neopentyl glycol dicaprate, 2-butyl-2-ethyl-1,3-propanediol dioctanoate, propylene glycol dioleate, pentaerythrityl tetraoctanoate, hydrogenated rosin pentaerythrityl, ditrimethylolpropane triethylhexanoate, (isostearate/sebacate) ditrimethylolpropane, pentaerythrityl triethylhexanoate, (hydroxystearate/stearate/rosinate) dipentaerythrityl Polyhydric alcohol fatty acid esters such as diglyceryl diisostearate, polyglyceryl tetraisostearate, polyglyceryl-10 nonaisostearate, polyglyceryl-8 erucate/isostearate/ricinoleate, diglyceryl oligoesters (hexyldecanoate/sebacate), glycol distearate (ethylene glycol distearate), polyhydric alcohol fatty acid esters such as 3-methyl-1,5-pentanediol dieopentanoate and 2,4-diethyl-1,5-pentanediol dieopentanoate; alkyl ethers such as dicaprylyl ether; diisopropyl dimer dilinoleate Dimer acids or dimer ol derivatives such as diisostearyl dimer dilinoleate, di(isostearyl/phytosteryl) dimer dilinoleate, (phytosteryl/behenyl) dimer dilinoleate, (phytosteryl/isostearyl/cetyl/stearyl/behenyl) dimer dilinoleyl dimer dilinoleate, dimer dilinoleyl diisostearate, hydrogenated rosin condensate of dimer dilinoleyl, hydrogenated castor oil of dimer dilinoleate, hydroxyalkyl dimer dilinoleyl ether; coconut oil fatty acid monoethanolamide (cocamide ME A) Fatty acid alkanolamides such as coconut oil fatty acid diethanolamide (cocamide DEA), lauric acid monoethanolamide (lauramide MEA), lauric acid diethanolamide (lauramide DEA), lauric acid monoisopropanolamide (lauramide MIPA), palmitic acid monoethanolamide (palmitamide MEA), palmitic acid diethanolamide (palmitamide DEA), coconut oil fatty acid methylethanolamide (cocamide methyl MEA); dimethicone (dimethylpolysiloxane), highly polymerized dimethicone (highly polymerized dimethylpolysiloxane), cyclomethicone (cyclic dimethicone) Silicones such as lusiloxane, decamethylcyclopentasiloxane, phenyl trimethicone, diphenyl dimethicone, phenyl dimethicone, (aminoethylaminopropyl methicone/dimethicone) copolymer, dimethiconol, dimethiconol crosspolymer, silicone resins, silicone rubber, amino-modified silicones such as aminopropyl dimethicone and amodimethicone, cationic-modified silicones, polyether-modified silicones such as dimethicone copolyol, polyglycerin-modified silicones, sugar-modified silicones, carboxylic acid-modified silicones, phosphate-modified silicones, sulfuric acid-modified silicones, alkyl-modified silicones, fatty acid-modified silicones, alkyl ether-modified silicones, amino acid-modified silicones, peptide-modified silicones, fluorine-modified silicones, cationic-modified and polyether-modified silicones, amino-modified and polyether-modified silicones, alkyl-modified and polyether-modified silicones, amide-alkyl-modified silicones, amino glycol-modified silicones, aminophenyl-modified silicones, and polysiloxane/oxyalkylene copolymers are preferred; fluorine-based oils such as perfluorodecane, perfluorooctane, and perfluoropolyether are also preferred.

As moisturizers and texture enhancers, these include glycerin, 1,3-butylene glycol, propylene glycol, 3-methyl-1,3-butanediol, 1,3-propanediol, 2-methyl-1,3-propanediol, trimethylolpropane, pentaerythritol, hexylene glycol, diglycerin, polyglycerin, diethylene glycol, polyethylene glycol, dipropylene glycol, polypropylene glycol, polyols and their polymers such as ethylene glycol/propylene glycol copolymers; glycol alkyl ethers such as diethylene glycol monoethyl ether (ethoxydiglycol), ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, and diethylene glycol dibutyl ether; water-soluble esters such as (eicosanedioic acid/tetradecanedioic acid) polyglyceryl-10, tetradecanedioic acid polyglyceryl-10, and cyclohexanedicarboxylic acid bisethoxydiglycol; sorbitol, xylitol Sugar alcohols such as glucose, erythritol, mannitol, and maltitol; glucose, fructose, galactose, mannose, threose, xylose, arabinose, fucose, ribose, deoxyribose, maltose, trehalose, lactose, raffinose, gluconic acid, glucuronic acid, cyclodextrins (α-, β-, γ-cyclodextrins, and modified cyclodextrins such as maltosylation and hydroxyalkylation), β-glucan, chitin, chitosan, Heparin and its derivatives, pectin, arabinogalactan, dextrin, dextran, glycogen, ethyl glucoside, glucose glucosylethyl methacrylate polymers or copolymers, and other sugars and their derivatives; hyaluronic acid, sodium hyaluronate; sodium chondroitin sulfate; mucoitin sulfate, caronin sulfate, kerato sulfate, dermatan sulfate; Tremella fuciformis extract, Tremella fuciformis polysaccharide; inulin, levan and other fructans; fucoidan; tuberose polysaccharide, naturally derived polysaccharides Organic acids such as citric acid, tartaric acid, lactic acid and their salts; urea; 2-pyrrolidone-5-carboxylic acid and its sodium salts; betaine (trimethylglycine), proline, hydroxyproline, arginine, lysine, serine, glycine, alanine, phenylalanine, tyrosine, β-alanine, threonine, glutamic acid, glutamine, asparagine, aspartic acid, cysteine, cystine, methionine, leucine, isoleucine, valine, tryptophan, histidine, taurine, γ-aminobutyric acid, γ-amino-β-hydroxybutyric acid, carnitine, carnosine, creatine and other amino acids and their salts; collagen, fish-derived collagen, atelocollagen, gelatin, elastin, collagen-degraded peptides, hydrolyzed collagen, hydroxypropylammonium chloride hydrolyzed collagen, elastin-degraded peptides, keratin-degraded peptides, hydrolyzed keratin, conchiolin-degraded peptides, hydrolyzed conchiolin, silk protein-degraded peptides, hydrolyzed silk, lauro Protein peptides and their derivatives such as hydrolyzed silk sodium, soy protein hydrolysate, wheat protein hydrolysate, hydrolyzed wheat protein, casein hydrolysate, acylated peptides; acylated peptides such as palmitoyl oligopeptide, palmitoyl pentapeptide, palmitoyl tetrapeptide; silylated peptides; lactic acid bacteria culture solution, yeast extract, eggshell membrane protein, bovine submandibular gland mucin, hypotaurine, sesame lignan glycosides, glutathione, albumin, whey; choline chloride, phosphodiester Preferred ingredients include lylcholine; animal and plant extracts such as placental extract, aerlastin, collagen, aloe extract, witch hazel water, loofah water, chamomile extract, licorice extract, comfrey extract, silk extract, rose extract, yarrow extract, eucalyptus extract, and sweet clover extract; natural ceramides (types 1, 2, 3, 4, 5, and 6); hydroxyceramides; pseudoceramides; sphingoglycolipids; and ceramides such as ceramide and glycoceramide-containing extracts.

Preferred surfactants include anionic surfactants, nonionic surfactants, cationic surfactants, amphoteric surfactants, and polymeric surfactants. There are no particular restrictions on the HLB of the surfactant; those with low HLB values of around 1 to high HLB values of around 20 can be used, and it is also preferable to combine those with low and high HLB values. Examples of preferred surfactants include, among anionic surfactants, fatty acid salts such as potassium laurate and potassium myristate; alkyl sulfate esters such as sodium lauryl sulfate, triethanolamine lauryl sulfate, and ammonium lauryl sulfate; polyoxyethylene alkyl sulfates such as sodium laureth sulfate and triethanolamine laureth sulfate; and acyl N-methyl amino acid salts such as sodium cocoyl methyl taurate, potassium cocoyl methyl taurate, sodium lauroyl methyl taurate, sodium myristoyl methyl taurate, sodium lauroyl methylalanine, sodium lauroyl sarcosinate, triethanolamine lauroyl sarcosinate, and sodium lauroyl glutamate methylalanine. Acyl amino acid salts such as sodium cocoyl glutamate, triethanolamine cocoyl glutamate, sodium lauroyl glutamate, sodium myristoyl glutamate, sodium stearoyl glutamate, ditriethanolamine palmitoyl aspartate, triethanolamine cocoyl alanine, sodium dilauroyl glutamate lysine; polyoxyethylene alkyl ether acetates such as sodium laureth acetate; succinate ester salts such as sodium lauroyl monoethanolamide succinate; fatty acid alkanolamide ether carboxylates; acyl lactates; polyoxyethylene fatty acid amine sulfates; fatty acid alkanolamide sulfates; fatty acid glycerin sulfates such as hydrogenated coconut oil fatty acid glycerin sulfate Sulfates; alkylbenzene polyoxyethylene sulfates; olefin sulfonates such as sodium α-olefin sulfonate; alkyl sulfosuccinates such as disodium lauryl sulfosuccinate and sodium dioctyl sulfosuccinate; alkyl ether sulfosuccinates such as disodium laureth sulfosuccinate, monolauroyl monoethanolamide sodium polyoxyethylene sulfosuccinate, and sodium lauryl polypropylene glycol sulfosuccinate; alkylbenzene sulfonates such as sodium tetradecylbenzenesulfonate and triethanolamine tetradecylbenzenesulfonate; alkylnaphthalene sulfonates; alkanesulfonates; α-sulfo fatty acid methyl ester salts; acylumethionine Salts; alkylglycidyl ether sulfonates; alkyl sulfoacetates; alkyl ether phosphate salts such as sodium laureth phosphate, sodium dilaureth phosphate, sodium trilaureth phosphate, and sodium monooleth phosphate; alkyl phosphate salts such as potassium lauryl phosphate; sodium caseinate; alkylaryl ether phosphates; fatty acid amide ether phosphates; phospholipids such as phosphatidylglycerol, phosphatidylinositol, phosphatidic acid, cyclic lysophosphatidic acid or their salts; silicone-based anionic surfactants such as carboxylic acid-modified silicones, phosphate-modified silicones, and sulfate-modified silicones; nonionic surfactants include laureth (polyoxyethylene lauryl ether). Polyoxyethylene alkyl ethers of various polyoxyethylene addition numbers, such as ceteths (polyoxyethylene cetyl ethers), steareths (polyoxyethylene stearyl ethers), beheneths (polyoxyethylene behenyl ethers), isosteareths (polyoxyethylene isostearyl ethers), octyldodeceths (polyoxyethylene octyldodecyl ethers), etc.; polyoxyethylene alkylphenyl ethers; polyoxyethylene hydrogenated castor oil, polyoxyethylene castor oil, polyoxyethylene hydrogenated castor oil monoisostearate, polyoxyethylene hydrogenated castor oil triisostearate, polyoxyethylene hydrogenated castor oil monopyroglutamic acid monoisostearate diester, polyoxy Castor oil and hydrogenated castor oil derivatives such as hydrogenated castor oil maleic acid; polyoxyethylene phytosterol; polyoxyethylene cholesterol; polyoxyethylene cholestanol; polyoxyethylene lanolin; polyoxyethylene reduced lanolin; polyoxyethylene/polyoxypropylene cetyl ether, polyoxyethylene/polyoxypropylene 2-decyltetradecyl ether, polyoxyethylene/polyoxypropylene monobutyl ether, polyoxyethylene/polyoxypropylene hydrogenated lanolin, polyoxyethylene/polyoxypropylene glycerin ether, and other polyoxyethylene/polyoxypropylene alkyl ethers; polyoxyethylene/polyoxypropylene glycol; PPG (Poly)glycerin polyoxypropylene glycol such as -9 diglyceryl; glyceryl stearate, glyceryl isostearate, glyceryl palmitate, glyceryl myristate, glyceryl oleate, coconut oil fatty acid glyceryl, monocottonseed oil fatty acid glycerin, monoerucate glycerin, sesquioleate glycerin, α,α'-oleate pyroglutamate glycerin, monostearate glycerin malic acid and other glycerin fatty acid partial esters; polyglyceryl-2, 3, 4, 5, 6, 8, 10 stearate, polyglyceryl-6, 10 distearate, polyglyceryl-2 tristearate, polyglyceryl-10 decastearate, polyglyceryl-2, 3, 4, 5 isostearate Polyglycerin fatty acid esters such as 6, 8, 10, polyglyceryl-2 diisostearate (diglyceryl diisostearate), 3, 10, polyglyceryl-2 triisostearate, polyglyceryl-2 tetraisostearate, polyglyceryl-10 decaisostearate, polyglyceryl-2 oleate, 3, 4, 5, 6, 8, 10, polyglyceryl-6 dioleate, polyglyceryl-2 trioleate, polyglyceryl-10 decaoleate; ethylene glycol monofatty acid esters such as ethylene glycol monostearate; propylene glycol monofatty acid esters such as propylene glycol monostearate; pentaerythritol partial fatty acid ester; sorbitol partial fatty acid ester Spheric acid; maltitol partial fatty acid esters; maltitol ethers; sorbitan fatty acid esters such as sorbitan monooleate, sorbitan monoisostearate, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan sesquioleate, sorbitan trioleate, sorbitan penta-2-ethylhexyl diglycerol sorbitan, tetra-2-ethylhexyl diglycerol sorbitan; partial esters of sugar derivatives such as sucrose fatty acid esters, methyl glucoside fatty acid esters, and undecylenate trehalose; alkyl glucosides such as caprylyl glucoside; alkyl polyglycosides; glycolipids such as mannosyl erythritol lipid; lanolin alcohol; reduced lanolin; polyoxy Polyoxyethylene fatty acid mono and diesters such as polyethylene distearate, polyethylene glycol diisostearate, polyoxyethylene monooleate, polyoxyethylene dioleate; polyoxyethylene propylene glycol fatty acid esters; polyoxyethylene glycerin fatty acid esters such as polyoxyethylene monooleates such as polyoxyethylene glycerin monostearate, polyoxyethylene glycerin monoisostearate, polyoxyethylene glycerin triisostearate; polyoxyethylene sorbitan monooleate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan monooleate, polyoxyethylene sorbitan tetraoleate, etc. Ethylene sorbitan fatty acid esters; polyoxyethylene sorbitol fatty acid esters such as polyoxyethylene sorbitol monolaurate, polyoxyethylene sorbitol monooleate, polyoxyethylene sorbitol pentaoleate, and polyoxyethylene sorbitol monostearate; polyoxyethylene methyl glucoside fatty acid esters; polyoxyethylene alkyl ether fatty acid esters; polyoxyethylene animal and vegetable oils such as polyoxyethylene sorbitol beeswax; alkyl glyceryl ethers such as isostearyl glyceryl ether, chymyl alcohol, ceracyl alcohol, and batyl alcohol; polyhydric alcohol alkyl ethers; polyoxyethylene alkylamines; tetrapolyoxyethylene Lene-tetrapolyoxypropylene-ethylenediamine condensates; natural surfactants such as saponins and sophorolipids; polyoxyethylene fatty acid amides; fatty acid alkanolamides such as coconut oil fatty acid monoethanolamide (cocamide MEA), coconut oil fatty acid diethanolamide (cocamide DEA), lauric acid monoethanolamide (lauramide MEA), lauric acid diethanolamide (lauramide DEA), lauric acid monoisopropanolamide (lauramide MIPA), palmitic acid monoethanolamide (palmitamide MEA), palmitic acid diethanolamide (palmitamide DEA), coconut oil fatty acid methylethanolamide (cocamide methyl MEA); lauramine oxide, cocamine oxide, stearamine oxide Alkyldimethylamine oxides such as behenamine oxide; alkylethoxydimethylamine oxide; polyoxyethylene alkyl mercaptan; polyether-modified silicones such as dimethicone copolyol, polysiloxane-oxyalkylene copolymers, polyglycerin-modified silicones, sugar-modified silicones, and other silicone-based nonionic surfactants; cationic surfactants such as alkyltrimethylammonium chlorides such as behentrimonium chloride, steartrimonium chloride, cetrimonium chloride, and lauryltrimonium chloride; alkyltrimethylammonium bromides such as stearyltrimonium bromide; and dialkyldimethylammonium chlorides such as distearyldimonium chloride and dicocodimonium chloride. Ammonium chloride; fatty acid amide amines and their salts, such as stearamidopropyldimethylamine and stearamidoethyldiethylamine; alkyl etheramines and their salts or quaternary salts, such as stearoxypropyldimethylamine; fatty acid amide-type quaternary ammonium salts, such as ethyl sulfate long-chain branched fatty acid (12-31) aminopropylethyldimethylammonium and ethyl sulfate lanolin fatty acid aminopropylethyldimethylammonium; polyoxyethylene alkylamines and their salts or quaternary salts; alkylamine salts; fatty acid amide guanidium salts; alkyl etheramine mononium salts; alkyltrial chloromethylammonium salts; benzalkonium salts; benzethonium salts; pyridinium salts, such as cetylpyridinium chloride ;Imidazolinium salts;Alkylisoquinolinium salts;Dialkylmolyphonium salts;Polyamine fatty acid derivatives;Silicone-based cationic surfactants such as aminopropyl dimethicone and amodimethicone, cation-modified silicones, cation-modified and polyether-modified silicones, amino-modified and polyether-modified silicones;Amphoteric surfactants include N-alkyl-N,N-dimethylamino acid betaines such as lauryl betaine (lauryldimethylaminoacetic acid betaine);Fatty acid amide alkyl-N,N-dimethylamino acid betaines such as cocamidopropyl betaine and lauramidopropyl betaine;Imidazolin type betaines such as sodium cocoamphoacetate and sodium lauroamphoacetate;Alkyldimethylta Alkyl sulfobetaines such as urin; sulfate-type betaines such as alkyldimethylaminoethanol sulfate; phosphate-type betaines such as alkyldimethylaminoethanol phosphate; sphingophospholipids such as phosphatidylcholine, phosphatidylethanolamine, phosphatidylserine, and sphingomyelin; phospholipids such as lysolecithin, hydrogenated soybean phospholipid, partially hydrogenated soybean phospholipid, hydrogenated egg yolk phospholipid, partially hydrogenated egg yolk phospholipid, and hydroxylated lecithin; silicone-based amphoteric surfactants, etc.; polymeric surfactants include polyvinyl alcohol, sodium alginate, starch derivatives, tragacanth gum, and acrylic acid/alkyl methacrylate copolymers; various silicone-based surfactants are also preferred.

Examples of polymers, thickeners, and gelling agents include guar gum, locust bean gum, queen seed gum, carrageenan, galactan, gum arabic, tara gum, tamarind, fercerelan, karaya gum, okra gum, tragacanth gum, pectin, pectic acid and its salts, alginic acid and its salts, mannan; starches from rice, corn, potato, wheat, etc.; xanthan gum, dextran, succinoglucan, curdlan, hyaluronic acid and its salts, xanthan gum, pullulan, gellan gum, chitin, and chitosan. Agar, cassia seed extract, chondroitin sulfate, casein, collagen, gelatin, albumin; methylcellulose, ethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, carboxymethylcellulose and its sodium salts, methylhydroxypropylcellulose, carboxylated cellulose nanofibers, carboxymethylated cellulose nanofibers, phosphate-esterified cellulose nanofibers, sulfonated cellulose nanofibers, sodium cellulose sulfate, dialkyldimethylammonium sulfate Cellulose and its derivatives such as rose, crystalline cellulose, and cellulose powder; starch-based polymers such as soluble starch, carboxymethyl starch, methylhydroxypropyl starch, and methyl starch; starch derivatives such as hydroxypropyltrimonium chloride starch and corn starch aluminum octenyl succinate; alginic acid derivatives such as sodium alginate and propylene glycol alginate; polyvinylpyridone (PVP), polyvinyl alcohol (PVA), vinylpyridone/vinyl alcohol copolymer, and polyvinyl methyl ether; polyethylene glycol, polypropylene glycol, and polyoxyethylene/polyoxypropylene copolymer; amphoteric methacrylate copolymers such as (methacryloyloxyethyl carboxybetaine/alkyl methacrylate) copolymer and (acrylates/stearyl acrylate/ethylamine oxide methacrylate) copolymer; (dimethicone/vinyl dimethicone) crosspolymer, (alkyl acrylate/diacetone acrylamide) copolymer, and (alkyl acrylate/diacetone acrylamide) copolymer AMP; and polyvinyl acetate. Partially saponified products, maleic acid copolymers; vinylpyrrolidone/dialkylaminoalkyl methacrylate copolymers; acrylic resin alkanolamines; polyesters, water-dispersible polyesters; polyacrylamide; polyacrylic acid ester copolymers such as ethyl polyacrylate, carboxyvinyl polymers, salts such as polyacrylic acid and its sodium salt, acrylic acid/methacrylic acid ester copolymers; acrylic acid/alkyl methacrylate copolymers; cationized cellulose such as polyquaternium-10, diallyldimethylammonium chloride/acrylamide copolymers such as polyquaternium-7, acrylic acid/diallyldimethylammonium chloride copolymers such as polyquaternium-22, acrylic acid/diallyldimethylammonium chloride/acrylamide copolymers such as polyquaternium-39, acrylic acid/cationized methacrylic acid ester copolymers, acrylic acid/cationized methacrylamide copolymers, acrylic acid/methyl acrylate/methacrylamidopropyltrimethylammonium chloride copolymers such as polyquaternium-47, choline methacrylate chloride polymers; cationized oligosaccharides, Cationic polysaccharides such as cationized dextran and guar hydroxypropyltrimonium chloride; polyethyleneimines; cationic polymers; copolymers of 2-methacryloyloxyethyl phosphorylcholine polymers such as polyquaternium-51 and butyl methacrylate copolymers; polymer emulsions such as acrylic resin emulsions, ethyl polyacrylate emulsions, polyacrylic alkyl ester emulsions, polyvinyl acetate resin emulsions, natural rubber latex, and synthetic latex; nitrocellulose; polyurethanes and various copolymers; various silicones; various silicone-based copolymers such as acrylic-silicone graft copolymers; various fluorine-based polymers; 12-hydroxystearic acid and its salts; dextrin fatty acid esters such as dextrin palmitate and dextrin myristate; anhydrous silicic acid, fuzzy silica (ultrafine particle anhydrous silicic acid), aluminum magnesium silicate, sodium magnesium silicate, metal soaps, dialkyl metal phosphates, bentonite, hectorite, organically modified clay minerals, sucrose fatty acid esters, and fructooligosaccharide fatty acid esters are among the preferred materials.

Preferred antioxidants include tocopherol (vitamin E), tocopherol derivatives such as tocopherol acetate; BHT, BHA; gallic acid derivatives such as propyl gallate; vitamin C (ascorbic acid) and/or its derivatives; erythorbic acid and its derivatives; sulfites such as sodium sulfite; bisulfites such as sodium bisulfite; thiosulfates such as sodium thiosulfate; metabisulfites; thiotaurine, hypotaurine; thioglycerol, thiourea, thioglycolic acid, and cysteine hydrochloride. Preferred reducing agents include thioglycolic acid, cysteine, and cysteamine. Preferred oxidizing agents include hydrogen peroxide, ammonium persulfate, sodium bromate, and percarbonate. Antioxidants include ascorbic acid, ascorbic acid phosphate salts such as sodium ascorbic acid phosphate and magnesium ascorbic acid phosphate; ascorbic acid fatty acid esters such as monostearate, monopalmitate, dipalmitate, and tetraisopalmitate; ascorbic acid ethers such as 3-O-ethyl ascorbic acid, 2-O-ethyl ascorbic acid, cetyl ascorbic acid, glyceryl ascorbic acid, and hexylglyceryl ascorbic acid; ascorbic acid glucosides such as ascorbic acid-2-glucoside and their fatty acid esters; and ascorbic acid Preferred materials include ascorbic acid derivatives such as sulfuric acid esters and tocopheryl ascorbyl phosphate; vitamin A derivatives such as retinol, retinyl acetate, retinyl palmitate, and hydrogenated retinol; vitamin E derivatives such as tocopherol, tocopherol acetate, and tocotrienol; carotenoids such as carotene, lycopene, astaxanthin, and lutein; polyphenols such as phlorotannin, curcumin, anthocyanin, proanthocyanidin, catechin, ellagic acid, quercetin, and apple polyphenols; and coenzyme Q10, lipoic acid, lactoferrin, sesamin, hesperidin, protoanthocyanidin, lignan, chlorogenic acid, rutin, fullerene, and platinum nanocolloids.

As whitening agents, hydroquinone glycosides such as arbutin and α-arbutin and their esters; ascorbic acid phosphate salts such as ascorbic acid, sodium ascorbic acid phosphate salt and magnesium ascorbic acid phosphate salt; ascorbic acid fatty acid esters such as ascorbic acid monostearate, ascorbic acid monopalmitate, ascorbic acid dipalmitate, and ascorbic acid tetraisopalmitate; and ascorbic acid esters such as 3-O-ethyl ascorbic acid, 2-O-ethyl ascorbic acid, cetyl ascorbic acid, glyceryl ascorbic acid, and hexylglyceryl ascorbic acid. Preferred materials include: ascorbic acid glucosides such as ascorbic acid-2-glucoside and their fatty acid esters; ascorbic acid derivatives such as ascorbic acid sulfate and tocopheryl ascorbyl phosphate; tranexamic acid derivatives such as tranexamic acid, tranexamic acid cetyl, and tranexamic acid amide; licorice extract-related substances such as glabridin, glabrene, liquiritin, and isoliquiritin; kojic acid, ellagic acid, ferulic acid and their derivatives; placenta extract, glutathione, oryzanol, butylresorcinol, oil-soluble chamomile extract, oil-soluble licorice extract, willow extract, and saxifrage extract.

Vitamins and their derivatives include: Vitamin A compounds such as retinol, retinyl acetate, and retinyl palmitate; Vitamin B compounds such as thiamine hydrochloride, thiamine sulfate, riboflavin, riboflavin acetate, pyridoxine hydrochloride, pyridoxine dioctanoate, pyridoxine dipalmitate, flavin adenine dinucleotide, cyanocobalamin, folic acid compounds, nicotinic acid compounds such as nicotinamide and benzyl nicotinate, and choline compounds; Vitamin C compounds such as ascorbic acid and its sodium salts; Vitamin D; Vitamin E compounds such as α, β, γ, and δ-tocopherols; other vitamins such as pantothenic acid and biotin; and ascorbic acid phosphate sodium salt and ascorbic acid phosphate magnesium salt. Preferred materials include ascorbic acid phosphate salts, ascorbic acid fatty acid esters such as tetraisopalmitic ascorbate, ascorbyl stearate, ascorbyl palmitate, and ascorbyl dipalmitate, alkyl ascorbic acid ethers such as ethyl ascorbate, ascorbic acid glucosides such as ascorbic acid-2-glucoside and their fatty acid esters, ascorbic acid derivatives such as tocopheryl ascorbyl phosphate; vitamin derivatives such as tocopherol nicotinate, tocopherol acetate, tocopherol linoleate, tocopherol ferulate, and tocopherol phosphate esters; tocotrienols; and various other vitamin derivatives.

The plant, animal, and microbial extracts include iris extract, angelica extract, Thujopsis dolabrata extract, asparagus extract, avocado extract, Hydrangea macrophylla extract, almond extract, marshmallow extract, arnica extract, aloe extract, apricot extract, apricot kernel extract, ginkgo extract, fig extract, fennel extract, turmeric extract, oolong tea extract, bearberry extract, rosehip extract, echinacea leaf extract, Enmeisou extract, scutellaria baicalensis extract, and laurel extract. Kudzu extract, Coptis japonica extract, Barley extract, Panax ginseng extract, St. John's wort extract, Lamium album extract, Ononis extract, Nasturtium officinale extract, Orange extract, Dried seawater, Seaweed extract, Persimmon leaf extract, Arctium moniliforme extract, Hydrolyzed elastin, Hydrolyzed wheat powder, Hydrolyzed silk, Pueraria lobata extract, Chamomile extract, Oil-soluble chamomile extract, Carrot extract, Artemisia capillaris extract, Avena sativa extract, Chloranthus erythrosora extract, Licorice extract, Oil-soluble Licorice extract, kiwi extract, bellflower extract, wood ear mushroom extract, cinchona extract, cucumber extract, paulownia leaf extract, guanosine, guava extract, Sophora flavescens extract, gardenia extract, bamboo grass extract, Sophora flavescens extract, walnut extract, chestnut extract, grapefruit extract, clematis extract, black rice extract, brown sugar extract, black vinegar extract, chlorella extract, mulberry extract, gentian extract, Geranium thunbergii extract, black tea extract, yeast extract, Magnolia bark extract Coffee extract, burdock extract, rice extract, fermented rice extract, fermented rice bran extract, rice germ oil, comfrey extract, collagen, lingonberry extract, asarum extract, bupleurum extract, umbilical cord extract, saffron extract, salvia extract, soapwort extract, bamboo extract, hawthorn extract, sunflower extract, sansho extract, shiitake mushroom extract, rehmannia extract, lithospermum extract, perilla extract, linden extract, meadowsweet extract, jatoba extract, peony extract Yak extract, ginger extract, calamus root extract, birch extract, white fungus extract, horsetail extract, stevia extract, stevia ferment, willow extract, ivy extract, hawthorn extract, elderflower extract, yarrow extract, peppermint extract, sage extract, mallow extract, chuanthus extract, swertia japonica extract, mulberry bark extract, rhubarb extract, soybean extract, jujube extract, thyme extract, ta Dandelion extract, lichen extract, tea extract, clove extract, cogongrass extract, citrus peel extract, tea tree oil, sweet tea extract, chili pepper extract, angelica extract, calendula extract, peach kernel extract, spruce extract, Houttuynia cordata extract, tomato extract, natto extract, carrot extract, garlic extract, wild rose extract, hibiscus extract, Ophiopogon extract, lotus extract, parsley extract, birch extract, honey, witch hazel extract, parietaria extract, toad lily Preferred extracts include Isodon japonicus extract, bisabolol, cypress extract, bifidobacteria extract, loquat extract, coltsfoot extract, butterbur extract, Poria cocos extract, butcher's broom extract, grape extract, grape seed extract, propolis, loofah extract, safflower extract, peppermint extract, linden extract, peony extract, hop extract, cypress extract, pine extract, horse chestnut extract, skunk cabbage extract, soapberry extract, lemon balm extract, mozuku extract, peach extract, cornflower extract, eucalyptus extract, saxifrage extract, yuzu extract, lily extract, coix seed extract, mugwort extract, lavender extract, green tea extract, eggshell membrane extract, apple extract, rooibos tea extract, reishi mushroom extract, lettuce extract, lemon extract, forsythia extract, astragalus extract, rose extract, rosemary extract, Roman chamomile extract, royal jelly extract, and Sanguisorba officinalis extract.

Examples of UV absorbers include benzoic acid-based UV absorbers such as para-aminobenzoic acid, para-aminobenzoic acid monoglycerin ester, N,N-dipropoxypara-aminobenzoate ethyl ester, N,N-diethoxypara-aminobenzoate ethyl ester, N,N-dimethylpara-aminobenzoate ethyl ester, N,N-dimethylpara-aminobenzoate butyl ester, and N,N-dimethylpara-aminobenzoate ethyl ester; anthranilic acid-based UV absorbers such as homomenthyl-N-acetylanthranilate; salicylic acid-based UV absorbers such as salicylic acid and its sodium salt, amyl salicylate, menthyl salicylate, homomenthyl salicylate, octyl salicylate, phenyl salicylate, benzyl salicylate, and p-isopropanolphenyl salicylate; octyl cinnamate, ethyl-4-isopropyl cinnamate, and methyl-2,5-diisopropyl Cinnamic acid-based UV absorbers such as pyr cinnamate, ethyl-2,4-diisopropyl cinnamate, methyl-2,4-diisopropyl cinnamate, propyl-p-methoxy cinnamate, isopropyl-p-methoxy cinnamate, isoamyl-p-methoxy cinnamate, 2-ethylhexyl-p-methoxy cinnamate (octyl paramethoxycinnamate), 2-ethoxyethyl-p-methoxy cinnamate (cinoxate), cyclohexyl-p-methoxy cinnamate, ethyl-α-cyano-β-phenyl cinnamate, 2-ethylhexyl-α-cyano-β-phenyl cinnamate (octocrine), glyceryl mono-2-ethylhexanoyl-diparamethoxy cinnamate, ferulic acid and its derivatives; 2,4-dihydroxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimeth Benzophenone-based UV absorbers such as xybenzophenone, 2,2',4,4'-tetrahydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone (oxybenzone-3), 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonate, 4-phenylbenzophenone, 2-ethylhexyl-4'-phenylbenzophenone-2-carboxylate, 2-hydroxy-4-n-octoxybenzophenone, 4-hydroxy-3-carboxybenzophenone; 3-(4'-methylbenzylidene)-d,l-camphor, 3-benzylidene-d,l-camphor; 2-phenyl-5-methylbenzoxazole; 2,2'-hydroxy-5-methylphenylbenzotriazole; 2-(2'-hydroxy-5'-t-octylphenyl)benzotriazole; 2-(2' Preferred materials include hydroxy-5'-methylphenylbenzotriazole; dibenzarazine; dianisioylmethane; 5-(3,3-dimethyl-2-norbornylidene)-3-pentan-2-one; dibenzoylmethane derivatives such as 4-t-butylmethoxydibenzoylmethane; octyltriazone; urocanic acid derivatives such as urocanic acid and ethyl urocanic acid; hydantoin derivatives such as 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, 1-(3,4-dimethoxyphenyl)-4,4-dimethyl-1,3-pentanedione, dimethoxybenzylidene dioxoimidazolidinepropionate 2-ethylhexyl; phenylbenzimidazol sulfonic acid; terephthalylidene dicamphor sulfonic acid; drometrizole trisiloxane; methyl anthranilate; rutin and its derivatives; and oryzanol and its derivatives.

As antibacterial and preservative agents, parabens (hydroxybenzoic acid esters) such as methylparaben, ethylparaben, propylparaben, and butylparaben; phenoxyethanol; 1,2-alkanediols such as 1,2-pentanediol, 1,2-hexanediol, and 1,2-octanediol; alkylglyceryl ethers such as 2-ethylhexylglyceryl ether (ethylhexylglycerin); salicylic acid; lanolin fatty acids and their salts; sodium benzoate; isothiazolinone derivatives such as methylchloroisothiazolinone and methylisothiazolinone; imidazolinium urea; dehydroacetic acid and its salts; phenols; halogenated bisphenols such as triclosan, acid amides, quaternary ammonium salts; trichlorocarbanide, zinc pyrithione, benzalkonium chloride Preferred agents include benzethonium chloride, sorbic acid, chlorhexidine, chlorhexidine gluconate, halocarban, hexachlorophene, hinokitiol; phenols, isopropylphenol, cresol, thymol, parachlorophenol, phenylphenol, sodium phenylphenol, and other phenols; phenylethyl alcohol, photosensitizers, antimicrobial zeolites, and silver ions. However, when used as an antimicrobial or preservative for preservation purposes, from the viewpoint of safety for cosmetics or topical skin preparations, phenoxyethanol; 1,2-alkanediols such as 1,2-pentanediol, 1,2-hexanediol, and 1,2-octanediol; and alkylglyceryl ethers such as 2-ethylhexylglyceryl ether are more preferable.

Preferred chelating agents include edetates (ethylenediaminetetraacetate) such as EDTA, EDTA2Na, EDTA3Na, and EDTA4Na; hydroxyethylethylenediaminetriacetate such as HEDTA3Na; pentetates (diethylenetriaminepentaacetate); phytic acid; phosphonic acids such as etidronic acid and their sodium salts; sodium oxalate; polypolyamino acids such as polyaspartic acid and polyglutamic acid; sodium polyphosphate, sodium metaphosphate, phosphoric acid; sodium citrate, citric acid, alanine, dihydroxyethylglycine, gluconic acid, ascorbic acid, succinic acid, and tartaric acid.

Preferred pH adjusters, acids, and alkalis include citric acid, sodium citrate, lactic acid, sodium lactate, glycolic acid, succinic acid, acetic acid, sodium acetate, malic acid, tartaric acid, fumaric acid, phosphoric acid, hydrochloric acid, sulfuric acid, monoethanolamine, diethanolamine, triethanolamine, isopropanolamine, triisopropanolamine, 2-amino-2-methyl-1,3-propanediol, 2-amino-2-hydroxymethyl-1,3-propanediol, arginine, sodium hydroxide, potassium hydroxide, aqueous ammonia, guanidine carbonate, and ammonium carbonate.

Solvents and propellants include lower alcohols such as ethanol, 2-propanol (isopropyl alcohol), butanol, and isobutyl alcohol; glycols such as propylene glycol, 1,3-butylene glycol, diethylene glycol, dipropylene glycol, and isopentyl diol; diethylene glycol monoethyl ether (ethoxydiglycol), ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, triethylene glycol monoethyl ether, diethylene glycol diethyl ether, diethylene glycol dibutyl ether, propylene glycol monoethyl ether, and di Preferred propellants include glycol ethers such as propylene glycol monoethyl ether; glycol ether esters such as ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, and propylene glycol monoethyl ether acetate; glycol esters such as diethoxyethyl succinate and ethylene glycol disuccinate; benzyl alcohol, benzyloxyethanol, propylene carbonate, dialkyl carbonate, acetone, ethyl acetate, N-methylpyrrolidone; toluene; fluorocarbons, next-generation chlorofluorocarbons; LPG, dimethyl ether, and carbon dioxide.

Examples of antipruritic agents include diphenhydramine hydrochloride, chlorpheniramine maleate, camphor, and substance-P inhibitors. Examples of exfoliating and dissolving agents include salicylic acid, sulfur, resorcinol, selenium sulfide, pyridoxine, and glycolic acid. Examples of antiperspirants include aluminum chlorohydrate, aluminum chloride, zinc oxide, and zinc paraphenolsulfonate. Examples of cooling agents include menthol and methyl salicylate. Examples of astringent agents include citric acid, tartaric acid, lactic acid, potassium aluminum sulfate, tannic acid, and caffeine. Examples of enzymes include superoxide dismutase, catalase, lysozyme chloride, lipase, papain, pancreatin, and protease. Preferred nucleic acids include ribonucleic acid and its salts, deoxyribonucleic acid and its salts, and adenosine triphosphate disodium.

Preferred anti-inflammatory agents include glycyrrhizic acid and its derivatives, glycyrrhetinic acid derivatives, salicylic acid and its derivatives, azelaic acid and its derivatives, hinokitiol, guaiazulene, allantoin, indomethacin, zinc oxide, hydrocortisone acetate, prednisone, diphedramine hydrochloride, chlorpheniramine maleate; and plant extracts such as peach leaf extract and mugwort leaf extract. Preferred hair growth agents, blood circulation promoters, and stimulants include plant extracts and tinctures such as Swertia japonica extract, Capsicum tincture, Ginger tincture, Ginger extract, and Cantharis tincture; capsaicin, nonylic acid valenylamide, gingerol, ichthammol, tannic acid, borneol, cyclandelate, cinnarizine, trazoline, acetylcholine, verapamil, cepharanthine, γ-oryzanol, cepharanthine, vitamin E and derivatives such as tocopherol nicotinate and tocopherol acetate; γ-oryzanol, nicotinic acid and derivatives such as nicotinamide, benzyl nicotinate, inositol hexanicotinate, and nicotinic alcohol; allantoin, photosensitizer 301, photosensitizer 401, capronium chloride, pentadecanoic acid monoglyceride, flavanonol derivatives, stigmasterol or stigmamanol and its glycosides; and minoxidil. Preferred hormones include estradiol, estrone, ethinylestradiol, cortisone, hydrocortisone, and prednisone.

As anti-wrinkle and anti-aging agents, these include ascorbic acid, ascorbic acid phosphate salts such as sodium ascorbic acid phosphate and magnesium ascorbic acid phosphate; ascorbic acid fatty acid esters such as ascorbic acid monostearate, ascorbic acid monopalmitate, ascorbic acid dipalmitate, and ascorbic acid tetraisopalmitate; ascorbic acid ethers such as 3-O-ethyl ascorbic acid, 2-O-ethyl ascorbic acid, cetyl ascorbic acid, glyceryl ascorbic acid, and hexylglyceryl ascorbic acid; ascorbic acid glucosides such as ascorbic acid-2-glucoside and their fatty acid esters; and ascorbic acid derivatives such as ascorbic acid sulfate and tocopheryl ascorbyl phosphate. Preferred materials include: Vitamin A compounds such as retinol, retinyl acetate, retinyl palmitate, and hydrogenated retinol; nicotinamide, glutathione, cysteine, crocetin, sericin, geraniol, glycerin glucoside, lactoferrin, proanthocyanidin, pantothenic acid, panthenol, soy saponin, revelastol, isoflavone, coenzyme Q10, chondroitin sulfate, acetylglucosamine, glycerophosphatidylcholine, hydrolyzed hyaluronic acid, collagen peptide, conchiolin hydrolysate, adenosine 5'-monophosphate, phosphatidylinositol, sodium trifluoride isopropyl oxopropylaminocarbonylpyrrolidinecarbonylmethylpropylaminocarbonylbenzoylaminoacetate, tranexamic acid and its derivatives.

Preferred irritation-reducing agents include mannosylerythritol lipid, diethylene glycol dimer dilinoleate oligomer ester, diisostearyl malate, N-acyl-L-glutamic acid, trehalose mono-fatty acid ester, fatty acid amidoamine oxide, alkyldimethylamine oxide, phenylethyl glucoside, lauryl glucoside, ferulic acid glucoside, salicin, cedrol, polyethylene glycol, and polypropylene glycol. Preferred cooling agents include menthol, camphor, menthyl lactate, monomentyl succinate, menthyl acetate, borneol, cineole, thymol, peppermint oil, and derivatives thereof. Preferred warming agents include vanillin and its derivatives, vanillyl nonanoate, gingerol, capsicum tincture, capsicum extract, benzyl nicotinate, methyl nicotinate, phenyl nicotinate, tocopherol nicotinate and other nicotinic acid derivatives, capsaicin, watercress extract, sansho pepper extract, ginger extract, and canthari extract.

Powders include mica, talc, kaolin, sericite, montmorillonite, kaolinite, mica, muscovite, phlogopite, synthetic mica, red mica, biotite, vermiculite, magnesium carbonate, calcium carbonate, aluminum silicate, barium silicate, calcium silicate, magnesium silicate, strontium silicate, tungstate metal salts, magnesium, zeolite, barium sulfate, calcined calcium sulfate, calcium phosphate, fluorapatite, hydroxyapatite, ceramic powder, bentonite, smectite, clay, mud, metal soaps (e.g., zinc myristate, calcium palmitate, aluminum stearate), calcium carbonate, red iron oxide, yellow iron oxide, black iron oxide, ultramarine, Prussian blue, carbon black, titanium dioxide, fine and ultrafine titanium dioxide, zinc oxide, fine and ultrafine zinc oxide, alumina, silica, fuzzy silica (ultrafine anhydrous silicic acid), and titanium mica. Preferred materials include inorganic powders of various sizes and shapes such as fish scale foil, boron nitride, photochromic pigments, synthetic fluorphlogopite, fine particle composite powders, gold, aluminum, and inorganic powders that have been hydrophobized or hydrophilized by treating them with various surface treatment agents such as hydrogen silicone, cyclic hydrogen silicone, or other silanes or titanium coupling agents; organic powders of various sizes and shapes such as starch, cellulose, nylon powder, polyethylene powder, polymethyl methacrylate powder, polystyrene powder, styrene-acrylic acid copolymer resin powder, polyester powder, benzoguanamine resin powder, polyethylene terephthalate/polymethyl methacrylate laminated powder, polyethylene terephthalate/aluminum/epoxy laminated powder, urethane powder, silicone powder, Teflon® powder, and other organic powders and surface-treated powders, as well as organic-inorganic composite powders. Preferred inorganic salts include sodium chloride-containing salts such as table salt, regular salt, rock salt, sea salt, and natural salt; potassium chloride, aluminum chloride, calcium chloride, magnesium chloride, bittern, zinc chloride, and ammonium chloride; sodium sulfate, aluminum sulfate, aluminum potassium sulfate (alum), aluminum ammonium sulfate, barium sulfate, calcium sulfate, potassium sulfate, magnesium sulfate, zinc sulfate, iron sulfate, and copper sulfate; and sodium phosphates such as 1Na, 2Na, and 3Na phosphates, potassium phosphates, calcium phosphates, and magnesium phosphates.

As pigments, colorants, dyes, and pigments, we have Brown No. 201, Black No. 401, Purple No. 201, Purple No. 401, Blue No. 1, Blue No. 2, Blue No. 201, Blue No. 202, Blue No. 203, Blue No. 204, Blue No. 205, Blue No. 403, Blue No. 404, Green No. 3, Green No. 201, Green No. 202, Green No. 204, Green No. 205, Green No. 3, Green No. 401, Green No. 402 Red No. 102, Red No. 104-1, Red No. 105-1, Red No. 106, Red No. 2, Red No. 3, Red No. 201, Red No. 202, Red No. 203, Red No. 204, Red No. 205, Red No. 206, Red No. 207, Red No. 208, Red No. 213, Red No. 214, Red No. 215, Red No. 218, Red No. 219, Red No. 220, Red No. 221, Red No. 223 , Red No. 225, Red No. 226, Red No. 227, Red No. 228, Red No. 230-1, Red No. 230-2, Red No. 231, Red No. 232, Red No. 3, Red No. 401, Red No. 40 No. 4, Red No. 405, Red No. 501, Red No. 502, Red No. 503, Red No. 504, Red No. 505, Red No. 506, Orange No. 201, Orange No. 203, Orange No. 204, Orange 20 No. 5, Orange No. 206, Orange No. 207, Orange No. 401, Orange No. 402, Orange No. 403, Yellow No. 201, Yellow No. 202-1, Yellow No. 202-2, Yellow No. 203, Yellow No. 204, Legal dyes such as Yellow No. 205, Yellow No. 4, Yellow No. 401, Yellow No. 402, Yellow No. 403-1, Yellow No. 404, Yellow No. 405, Yellow No. 406, Yellow No. 407, Yellow No. 5; Acid Other acidic dyes such as Red 14; Basic dyes such as Arianor Sienna Brown, Arianor Madder Red, Arianor Steel Blue, Arianor Straw Yellow; HC Yellow 2, HC Yellow 5, HC Red 3, 4-hydroxypropylamino-3-nitrophenol, N,N’-bis(2-hydroxyethyl)-2-nitro-p-phenylenediamine, HC Blue 2, Basic Blue Nitro dyes such as 26; disperse dyes; inorganic white pigments such as titanium dioxide and zinc oxide; inorganic red pigments such as iron oxide (red iron oxide) and iron titanate; inorganic brown pigments such as γ-iron oxide; inorganic yellow pigments such as yellow iron oxide and ochre; inorganic black pigments such as black iron oxide and lower titanium oxide; inorganic purple pigments such as mango violet and cobalt violet; inorganic green pigments such as chromium oxide, chromium hydroxide, and cobalt titanate; inorganic blue pigments such as ultramarine and Prussian blue; pearl pigments such as titanium dioxide-coated mica, titanium dioxide-coated bismuth oxychloride, titanium dioxide-coated talc, colored titanium dioxide-coated mica, bismuth oxychloride, and fish scale foil; metal powder pigments such as aluminum powder, copper powder, and gold; astaxanthin, aliza Natural pigments and dyes such as anthraquinones (e.g., phosphorus), anthocyanidins, β-carotene, catenal, capsanthin, chalcone, calsamine, quercetin, crocin, chlorophyll, curcumin, naphthoquinones (e.g., cochineal, shikonin), bixin, flavones, betacyanidin, henna, hemoglobin, lycopene, riboflavin, rutin, and other natural pigments and dyes; oxidative dye intermediates and couplers such as p-phenylenediamine, toluene-2,5-diamine, o-, m-, or p-aminophenol, m-phenylenediamine, 5-amino-2-methylphenol, resorcinol, 1-naphthol, 2,6-diaminopyridine, and their salts; auto-oxidative dyes such as indoline; and dihydroxyacetone are preferred.

The fragrance ingredients include acetyl cedrene, amyl cinnamaldehyde, allyl amyl glycolate, β-ionone, iso-esuper, isobutyl quinoline, iris oil, ylone, indole, ylang-ylang oil, undecanal, undecenal, γ-undecalactone, estragol, eugenol, oakmoss, opoponax resinoid, orange oil, eugenol, aurantiol, galacsolid, carvacrol, L-carbone, camphor, canone, carrot seed oil, clove oil, methyl cinnamate, geraniol, geranyl nitrile, and isobornyl acetate. Geranyl acetate, dimethylbenzylcarbinyl acetate, styraryl acetate, cedyl acetate, terepinel acetate, p-t-butylcyclohexyl acetate, vetiveryl acetate, benzyl acetate, linalyl acetate, isopentyl salicylate, benzyl salicylate, sandalwood oil, santalol, cyclamenaldehyde, cyclopentadecanol, methyl dihydrojasmonate, dihydromyrcenolate, jasmine absolute, jasmine lactone, cis-jasmone, citral, citronenol, citronellal, cinnamon bark oil, 1,8-cineole, cinnamaldehyde, s Thylax resinoid, cedarwood oil, cedrene, cedrol, celery seed oil, thyme oil, damascone, damacenone, thymol, tuberose absolute, decanal, decalactone, terpineol, γ-terpinene, tripral, nerol, nonanal, 2,6-nonadienol, nonalactone, patchouli alcohol, vanilla absolute, vanillin, basil oil, patchouli oil, hydroxycitronellal, α-pinene, piperitone, phenethyl alcohol, phenylacetaldehyde, petitgrain oil, hexyl cinnamaldehyde, cis-3-hexeno Preferred examples include synthetic and natural fragrances such as ol, peruvian balsam, vetiver oil, vetiverol, peppermint oil, pepper oil, heliotropin, bergamot oil, benzyl benzoate, borneol, myrrhizinoid, musk ketone, methyl nonylacetaldehyde, γ-methylionone, menthol, L-menthol, L-menthone, eucalyptus oil, β-ionone, lime oil, lavender oil, D-limonene, linalool, liral, lilial, lemon oil, rose absolute, rose oxide, rose oil, rosemary oil, various essential oils, and various blended fragrances.

In addition to tap water and purified water, preferred types of water include hard water, soft water, natural water, deep-sea water, electrolyzed alkaline ionized water, electrolyzed acidic ionized water, ionized water, and clustered water.

In addition to the above, it is possible to include known cosmetic ingredients, pharmaceutical ingredients, and food ingredients in known combinations, formulation ratios, and amounts, including ingredients listed in the Cosmetic Ingredient Standards, Cosmetic Ingredient Formulation Standards, Japan Cosmetic Industry Association Ingredient Labeling Name List, INCI Dictionary (The International Cosmetic Ingredient Dictionary and Handbook), Quasi-drug Ingredient Standards, Japanese Pharmacopoeia, Pharmaceutical Additive Standards, Food Additives, etc., as well as ingredients listed in Japanese and foreign patent gazettes and patent publications (including published and republished gazettes) belonging to the International Patent Classification IPC A61K7 and A61K8.

Examples of cosmetic compositions of the present invention include hair cosmetics, skin cosmetics, makeup cosmetics, fragrance cosmetics, and body cosmetics. The cosmetic compositions of the present invention can be manufactured according to conventional methods.

To further describe the types of cosmetics of the present invention, preferred hair cosmetics include shampoos such as oil shampoos, cream shampoos, conditioning shampoos, anti-dandruff shampoos, hair color shampoos, and rinse-integrated shampoos; hair care products such as rinses, conditioners, treatments, hair packs, leave-on treatments, hair mists, and hair oils; hair styling products such as hair foams, hair mousses, hair sprays, hair waxes, hair gels, hair creams, water greases, setting lotions, pomades, and hair sticks; hair dyes such as color lotions, hair color treatments, hair manicures, and oxidative hair dyes; and hair tonics, hair liquids, hair blow dryers, split end coats, permanent wave agents, straightening perm agents, hair bleaches, hair color pre-treatments, hair color after-treatments, perm pre-treatments, perm after-treatments, and hair growth agents.

As skin cosmetics, we offer a variety of products including: toners such as softening toners, astringent toners, cleansing toners, multi-layer toners, and liposome toners; lotions such as emollient lotions, moisturizing lotions, milky lotions, nourishing lotions, nourishing milks, skin moisturizers, moisturizing emulsions, massage lotions, exfoliating smoothers, elbow lotions, hand lotions, and body lotions; emollient creams, nourishing creams, nourishing creams, vanishing creams, moisturizing creams, night creams, massage creams, cleansing creams, makeup creams, base creams, pre-makeup creams, sunscreen creams, suntan creams, hair removal creams, deodorant creams, shaving creams, and keratin removers. Preferred products include: skincare cosmetics such as creams including softening creams, moisturizing gels, whitening gels, all-in-one gels, moisturizing essences, whitening essences, moisturizing serums, whitening serums, and other beauty serums; sunscreen cosmetics such as sun protectors, sun protection milks, and sunscreens; packs and masks such as peel-off packs, powder packs, washing packs, oil packs, and cleansing masks; cleansing cosmetics such as cleansing foams, cleansing creams, cleansing milks, cleansing lotions, cleansing gels, and cleansing oils; and facial cleansers such as paste facial cleansing foams, gel facial cleansing foams, foaming facial cleansing foams, facial cleansing powders, cosmetic soaps, clear soaps, medicated soaps, liquid soaps, and shaving soaps.

Preferred makeup products include lipstick, lip gloss, foundation, blush, face powder, concealer, eyeliner, mascara, eyeshadow, eyebrow pencil, eyebrow products, nail polish, nail polish remover, and nail treatment.

Preferred fragranced cosmetics include perfumes, fragrances, parfums, eau de parfums, eau de toilettes, eau de colognes, solid perfumes, fragrance powders, fragranced soaps, body lotions, and bath oils.

Preferred body cosmetics include body washes such as body shampoos, deodorant lotions, deodorant powders, deodorant sprays, deodorant sticks, deodorizing cosmetics, bleaching agents, depilatory agents, bath additives, and insect repellent sprays.

Preferred types of topical skin preparations of the present invention include ointments, lotions, creams or gels, patches, liniments, and liquid application preparations. They can also be used as oral cosmetics such as toothpaste and mouthwash.

Preferred dosage forms for the cosmetic or topical skin preparation of the present invention include emulsified cosmetics such as oil-in-water (O/W) type, water-in-oil (W/O) type, W/O/W type, and O/W/O type, as well as oily cosmetics, solid cosmetics, liquid cosmetics, paste cosmetics, stick cosmetics, volatile oil-type cosmetics, powder cosmetics, jelly-type cosmetics, gel-type cosmetics, paste-type cosmetics, emulsified polymer-type cosmetics, sheet-type cosmetics, mist-type cosmetics, and spray-type cosmetics.

The present invention will be described in more detail by the following examples, but the present invention is not limited thereto.

Example 1 Synthesis of β-Lysophosphatidic Acid In a 200 mL reaction vessel equipped with a stirrer, thermometer, gas inlet tube, and condenser, 21 g of soy lecithin (SLP-PC70, manufactured by Tsuji Oil Co., Ltd.) was dispersed in 120 g of 1.0 M sodium acetate buffer (pH 6.5) containing 0.3 M calcium chloride. Then, 0.21 g of phospholipase A2 (Nagase 10P/R, manufactured by Nagase Chemtec Co., Ltd.) was charged, and the reaction was stirred at 40°C for 20 hours. After the reaction, 2.1 g of EDTA was charged and stirred for 0.5 hours, then 0.7 g of phospholipase D (manufactured by Meito Sangyo Co., Ltd.) was charged, and the reaction was stirred at 40°C for 20 hours. After concentrating the resulting reaction solution, 210 g of acetone was added, and the precipitated solid was filtered off. 50.0 g of a 10% phosphoric acid aqueous solution was added to the obtained solid and stirred at 75°C for 1 hour to perform hydrolysis. Then, 415 g of acetone was added, and the precipitated solid was filtered off and dried to obtain a β-lysophosphatidic acid-containing substance as a yellow solid (yield 42.3%). The β-lysophosphatidic acid content was 25.8% by mass. The fatty acid composition was palmitic acid 27%, stearic acid 7%, oleic acid 6%, linoleic acid 50%, linolenic acid 6%, and others 4%.
2.5 g of the β-lysophosphatidic acid-containing material obtained above and 7.5 g of glycerin were stirred and mixed at 70°C for 3 hours to obtain a glycerin solution of β-lysophosphatidic acid.

Example 2 Synthesis of β-Lysophosphatidic Acid Aluminum 2.5 g of the β-lysophosphatidic acid-containing material obtained in Example 1, 7.375 g of glycerin, and 0.125 g of aluminum hydroxide were stirred and mixed at 70°C for 3 hours to obtain β-lysophosphatidic acid aluminum as a glycerin solution.

Example 3 Synthesis of β-Lysophosphatidic Acid Zinc 2.5 g of the β-Lysophosphatidic acid-containing material obtained in Example 1, 7.375 g of glycerin, and 0.125 g of zinc oxide were stirred and mixed at 70°C for 3 hours to obtain β-Lysophosphatidic acid zinc as a glycerin solution.

Example 4 Synthesis of β-lysophosphatidic acid β-lysophosphatidic acid was obtained by following the same procedure as in Example 1, except that a 10% aqueous citric acid solution was used instead of an aqueous 10% phosphoric acid solution.

Example 5 Synthesis of β-lysophosphatidic acid β-lysophosphatidic acid was obtained by following the same procedure as in Example 1, except that a 10% aqueous acetic acid solution was used instead of a 10% aqueous phosphoric acid solution.

<Evaluation of physiological activity>
Normal human epidermal keratinocytes were seeded in 24-well plates at a concentration of 1.0 × ^10⁵ cells/well and cultured in HuMedia-KB2 medium (Kurabo Industries Ltd.) for 16 hours. Then, each test substance listed in Table 1 was added to the medium at a concentration of 25 ppm, and the cells were cultured for a further 4 hours. Subsequently, the gene expression levels of various proteins (standardized by GAPDH) were measured by real-time PCR. As a control, the gene expression levels of various proteins were similarly measured without the addition of the test substances. The results are shown in Table 1 as relative values using the average of three wells, with the control expression level set to 100.

Table 1 shows that the β-lysophosphatidic acid of the present invention significantly increased the gene expression levels of HAS3, CLDN1, CLDN4, ZO-2, INV, and TGM compared to the control. HAS3 is a hyaluronic acid synthase abundant in the epidermis, and increased HAS3 gene expression leads to increased hyaluronic acid production in the epidermis. CLDN1, CLDN4, and ZO-2 are proteins that form tight junctions, which govern cell-cell adhesion; increased gene expression levels of these proteins lead to increased tight junction formation. INV is a protein that forms the cornified envelope, an insoluble membrane surrounding keratinocytes, and TGM is an enzyme that acts during the formation of the cornified envelope; increased gene expression levels of these proteins lead to increased maturation of the cornified envelope.

<Evaluation of Hyaluronic Acid Production Promotion>
In the culture medium supplemented with β-lysophosphatidic acid from Example 1, normal human epidermal keratinocytes (NHEK cells) were cultured for 72 hours, and the amount of hyaluronic acid in the supernatant was quantified by ELISA. As a control, the amount of hyaluronic acid in a culture medium without the test substance was similarly quantified. The results are shown in Table 2 as relative values with the control amount of hyaluronic acid set to 100%.

<Collagen production promotion evaluation>
In the culture medium supplemented with β-lysophosphatidic acid from Example 1, normal human dermal fibroblasts (NHDF cells) were cultured for 24 hours, and the amount of type I collagen in the supernatant was quantified by ELISA. As a control, the amount of type I collagen in a culture medium without the test substance was similarly quantified. The results are shown in Table 3 as relative values with the control amount of type I collagen set to 100%.

<Evaluation of Actin Fibre Enhancement>
In the culture medium supplemented with β-lysophosphatidic acid from Example 1, normal human epidermal keratinocytes (NHEK cells) or normal human dermal fibroblasts (NHDF cells) were cultured for 24 hours. After that, actin filaments in the medium were stained with phalloidin and observed under a fluorescence microscope, and the amount of actin filaments was measured using brightness as an indicator. As a control, the amount of actin filaments in a culture medium without the test substance was similarly measured. The results are shown in Table 4 as relative values with the amount of actin filaments in the control set to 100%.

<Evaluation of cell proliferation promotion>
In the culture medium supplemented with β-lysophosphatidic acid from Example 1, normal human epidermal keratinocytes (NHEK cells) or normal human dermal fibroblasts (NHDF cells) were cultured for 48 hours, and the number of viable cells was measured by absorbance using WST-8 as a chromogenic reagent. The number of viable cells in a culture medium without the test substance was similarly quantified as a control. The results are shown in Table 5 as relative values with the control number of viable cells set to 100%.

The results shown in Tables 2-5 indicate that the β-lysophosphatidic acid of the present invention has hyaluronic acid production-promoting, collagen production-promoting, actin filament-enhancing, and cell proliferation-promoting effects.

<Stimuli Assessment>
For each test substance listed in Table 6, a 1% aqueous solution was prepared and used as the test solution. The irritation of the obtained test solutions was evaluated using the SIRC-STE method, which is included in the OECD Test Guidelines (TG491), as an alternative to the Draize test using rabbits, which was a commonly used method for evaluating irritation to the eyes and mucous membranes.

Test method
Rabbit corneal epithelial cells (SIRCs) were seeded in 200 μL at a concentration of 6.0 × ^10³ cells/well in a 96-well plate and cultured for 4 days. After culture, the culture medium was removed, and 200 μL each of 5% physiological saline solution of the test solution, 0.05% physiological saline solution of the test solution, and physiological saline as a control were added. After exposure for 5 minutes, the test samples were removed and washed three times with PBS(-). Then, 200 μL of 0.5 mg/mL MTT solution was added and reacted for 2 hours. After removing the MTT solution, 200 μL of isopropanol containing 0.04 mol/L hydrochloric acid was added to extract formazan for 1 hour. After extraction, the absorbance at 570 nm (OD570) of the extract was measured using a microplate reader, and the cell viability was calculated using the average OD570 of the three wells with the following formula. The experiment was conducted three times, and the results are shown in Table 1 as the average cell viability obtained in each experiment.

Based on the results in Table 6, the zinc salt form of β-lysophosphatidic acid was considered to have the highest cell viability and lowest irritant properties.

The following cosmetic composition was prepared using the composition of the present invention. The resulting cosmetic composition exhibits excellent moisturizing and penetrating properties, and prevents fine lines and rough skin.

Example 6 Moisturizing lotion Ingredients Amount (weight %)
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Part A: 0.5g of glycerin solution of β-type aluminum lysophosphatidicate from Example 2
BG 5.0
1,2-pentanediol 3.0
Purified water 20.0
Part B Neosolue-Aqulio (Nippon Fine Chemical) 1.0
Glucosylceramide 0.5
Tremoist-TP (Nippon Fine Chemical) 0.1
EDTA-2Na 0.05
Phenoxyethanol 0.4
Purified water, an amount that totals 100.
(Preparation method)
Parts A and B were mixed uniformly at approximately 40°C. A and B were mixed together to form a homogeneous liquid.

Example 7 Moisturizing lotion Ingredients Amount (weight %)
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Glycerin solution of β-type zinc lysophosphatidicate from Example 3 3.0
Phenoxyethanol 0.4
Sodium citrate (appropriate amount) Purified water (total amount to 100)
(Preparation method)
All ingredients were mixed at approximately 40°C, and sodium citrate was added to achieve a pH of 6.5-7.0 to create a homogeneous solution.

Example 8 Moisturizing lotion Ingredients Amount (weight %)
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Glycerin solution of β-type aluminum lysophosphatidic acid from Example 2 1.0
Phenoxyethanol 0.4
Hydroxyethylcellulose 0.2
Carbomer 0.1
Arginine 0.1
Purified water, an amount that totals 100.
(Preparation method)
All components were uniformly mixed at approximately 40°C to obtain a homogeneous liquid.

Example 9 Moisturizing lotion Ingredients Amount (weight %)
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Part A: 0.5g of glycerin solution of β-type aluminum lysophosphatidicate from Example 2
Diglycerin 1.0
Glycerin 8.0
BG 3.0
Plandool-LG2 (Nippon Seika) 0.1
Plandool-ISS (Nippon Fine Chemical) 0.05
Cholesterol 0.1
Part B Purified water 30.0
Part C: Maltitol solution 1.0
Betaine 0.5
α-Glucan Oligosaccharide 0.1
Pullulan 0.5
Tuberose polysaccharide 0.01
Hydroxypropyl methylcellulose stearoxy ether 0.05
(Acrylates/C10-30 Alkyl Acrylate) Crosspolymer 0.05
Arginine 0.05
Phenoxyethanol 0.2
Methylparaben 0.15
Purified water, an amount that totals 100.
(Preparation method)
Parts A and B were heated to 70°C each. Part A was added to Part B while stirring with a homomixer (7000 rpm) to prepare a nano-dispersion. The dispersion was then further dispersed using a high-pressure emulsifier (Mizuho Industries Microfluidizer). After cooling, pre-mixed Part C was added to create a homogeneous liquid.

Example 10 Moisturizing lotion Ingredients Amount (weight %)
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Part A: Glycerin solution of β-type aluminum lysophosphatidicate from Example 2 3.5
Diglycerin 1.0
Glycerin 8.0
Plandool-LG2 (Nippon Seika) 0.1
Plandool-ISS (Nippon Fine Chemical) 0.05
Phytosterol 0.1
Tocopherol 0.05
Part B Purified water 30.0
Section C: Betaine 0.5
Nicotinamide 5.0
Tranexamic acid (Nippon Seika) 1.0
Phenoxyethanol 0.2
Purified water, an amount that totals 100.
(Preparation method)
Parts A and B were heated to 70°C each. Part A was added to Part B while stirring with a homomixer (7000 rpm) to prepare a nano-dispersion. After cooling, Part C, which had been mixed beforehand, was added to create a homogeneous liquid.

Example 11 Moisturizing lotion Ingredients Amount (weight %)
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Part A: Glycerin solution of β-type aluminum lysophosphatidic acid from Example 2 5.0
BG 2.0
1,2-pentanediol 3.0
Purified water 20.0
Part B Neosolue-Aqulio (Nippon Fine Chemical) 1.0
Tranexamic acid (Nippon Seika) 2.0
Phenoxyethanol 0.4
Purified water, an amount that totals 100.
(Preparation method)
Parts A and B were mixed uniformly at approximately 40°C. A and B were mixed together to form a homogeneous liquid.

Example 12 Moisturizing lotion Ingredients Amount (weight %)
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Part A Phytopresome-MEL (Nippon Fine Chemical) 0.8
PrimeLipid-PI (Nippon Fine Chemical) 1.0
BG 5.0
Glycerin 10.0
1,2-Hexanediol 3.0
Part B: Purified water, in an amount that makes a total of 100. Part C: Glycerin solution of β-type aluminum lysophosphatidic acid from Example 2. 7.0
Sodium cyclic lysophosphatidic acid 0.001
Neosolue-AquaS (Nippon Fine Chemical) 1.0
PEG/PPG/Polybutylene Glycol-8/5/3 Glycerin 0.5
Polyquaternium-51 0.5
Phenoxyethanol 0.2
Methylparaben 0.15
Purified water 20.0
---------------------------------------------------------------------------
(Preparation method)
Parts A and B were heated to 70°C each. Part A was added to Part B while stirring with a homomixer (7000 rpm) to prepare the nanovesicle liquid. After further cooling, pre-mixed Part C was added to create a homogeneous liquid.

Example 13: Whitening lotion. Ingredients and amount (weight %).
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Glycerin solution of β-type aluminum lysophosphatidicate from Example 2 10.0
Glycerin 8.0
1,3-Propanediol 7.0
3-O-ethyl ascorbic acid (Nippon Seika) 1.0
Arbutin (Nippon Seika) 3.0
Ethanol 3.0
DPG 2.0
Methylgluceth-10 2.0
Dipotassium glycyrrhizate 0.05
Tremoist-TP (Nippon Fine Chemical) 0.01
Xanthan gum 0.05
Phenoxyethanol 0.2
Methylparaben 0.15
Citric acid 0.1
Sodium citrate 0.2
Purified water, an amount that totals 100.
(Preparation method)
All ingredients were weighed into a container and stirred with a paddle at room temperature to obtain a homogeneous liquid.

Example 14 Whitening lotion Ingredients Amount (weight %)
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Part A: Glycerin solution of β-type zinc lysophosphatidicate from Example 3 5.0
PrimeLipid-PI (Nippon Fine Chemical) 1.0
Tranexamic acid (Nippon Seika) 2.0
Nicotinamide 5.0
Phytic acid 0.3
Purified water 20.0
Part B BG 5.0
Tripropylene glycol 2.0
Sodium hyaluronate 0.01
DPG 2.0
Carbomer 0.01
Phenoxyethanol 0.4
Purified water, an amount that totals 100.
(Preparation method)
Parts A and B were each measured into containers and stirred with a paddle at room temperature to obtain a homogeneous liquid. Part A was then mixed with part B to obtain a homogeneous liquid.

Example 15 Gel lotion Ingredients Amount (weight %)
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Part A: Glycerin solution of β-type aluminum lysophosphatidic acid from Example 2 3.0
Glycerin 10.0
Sorbitol solution (70%) 5.0
PEG-10 Dimethicone 0.4
Glucose 1.0
BG 3.0
Purified water 20.0
Part B: Pullulan 0.2
Ethylhexylglycerin 0.2
Polymethacryloyl lysine 0.05
Crystalline cellulose powder 0.1
Locust bean gum 0.03
Hydroxyethylcellulose 0.05
Xanthan gum 0.05
Sodium hyaluronate 0.01
Inulin-SC (Nippon Fine Chemical) 1.0
Heparin-like substance 0.3
Dipotassium glycyrrhizate 0.1
Placenta extract 1.0
Centella asiatica extract 0.2
Tranexamic acid (Nippon Seika) 4.0
Carbomer 0.06
Purified water, an amount that totals 100.
(Preparation method)
Parts A and B were each measured into containers and stirred with a paddle at room temperature to obtain a homogeneous liquid. Part A was then mixed with part B to obtain a homogeneous liquid.

Example 16 Transparent Gel Ingredients Amount (weight %)
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Part A: Glycerin solution of β-type zinc lysophosphatidicate from Example 3 2.0
PrimeLipid-PI (Nippon Fine Chemical) 0.2
Glycerin 5.0
PPG-6 Decyltetradeceth-30 0.2
PEG-30 Phytosterol 0.3
Purified water 30.0
Part B PEG-4M 0.2
Methylgluceth-10 1.0
Pyridoxine hydrochloride 0.05
Ethylhexylglycerin 0.2
Phenoxyethanol 0.4
Tranexamic acid (Nippon Seika) 2.0
Tremoist-TP (Nippon Fine Chemical) 0.01
Hydrolyzed collagen 0.01
Purified water, in an amount that makes a total of 100 (ammonium dimethyltaurate acrylate/vinylpyrrolidone) copolymer 0.05
(Acrylates/C10-30 Alkyl Acrylate) Crosspolymer 0.15
Arginine 0.25
---------------------------------------------------------------------------
(Preparation method)
Parts A and B were each measured into containers and stirred with a paddle at room temperature to obtain a homogeneous liquid. Part A was then mixed with part B to obtain a homogeneous liquid.

Example 17: Scalp Lotion Ingredients and Amount (Weight %)
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Glycerin solution of β-lysophosphatidic acid zinc salt from Example 3 3.0
Maltitol solution 0.5
PEG-60 Hydrogenated Castor Oil 0.3
Ethanol 10.0
Neosolue-AquaS (Nippon Fine Chemical) 2.0
Betaine 0.2
Hydroxypropyl chitosan solution 0.05
Carrot extract 0.1
Pyridoxine hydrochloride 0.05
Panthenol 0.1
Dipotassium glycyrrhizinate 0.1
Phenoxyethanol 0.3
Purified water, an amount that totals 100.
(Preparation method)
All ingredients were weighed into a container and stirred with a paddle at room temperature to obtain a homogeneous liquid.

Example 18: Scalp Lotion Ingredients and Amount (Weight %)
------------------------------------------------------------------
Glycerin solution of β-lysophosphatidic acid zinc salt from Example 3 2.0
1,2-Hexanediol 1.0
Neosolue-Aqualio (Nippon Seika) 1.0
Tocopherol acetate 0.05
Menthol 0.1
Betaine 0.2
Swertia japonica extract 0.1
Stephania tetrandra root extract 0.003
Hinokitiol 0.1
PCA-Na 0.1
Carbomer 0.01
K hydroxide 0.01
Pentasodium pentetate 0.05
Phenoxyethanol 0.4
Purified water, an amount that totals 100.
(Preparation method)
All ingredients were weighed into a container and stirred with a paddle at room temperature to obtain a homogeneous liquid.

Example 19 Hair growth agent Ingredients and amount (weight %)
------------------------------------------------------------------
Glycerin 2.0
Glycerin solution of β-type zinc lysophosphatidicate from Example 3 1.0
PEG-60 Hydrogenated Castor Oil 0.3
Betaine 0.5
Ethanol 20.0
Menthol 0.1
Neosolue-AquaS (Nippon Fine Chemical) 2.0
Orange oil 0.05
Panthenyl ethyl ether 0.2
Carrot extract 1.0
Sophora angustifolia extract 2.0
Chlorella extract 1.0
Trehalose 0.5
Nicotinamide 1.0
Piroctone olamine 0.1
Dipotassium glycyrrhizinate 0.1
Purified water, an amount that totals 100.
(Preparation method)
All ingredients were weighed into a container and stirred with a paddle at room temperature to obtain a homogeneous liquid.

Example 20: Hair growth agent ingredients and their amounts (by weight)
------------------------------------------------------------------
Glycerin solution of β-type zinc lysophosphatidicate from Example 3 4.0
Phytopresome-MEL (Nippon Seika) 1.0
Neosolue-Aqualio (Nippon Seika) 0.5
DPG 2.0
Lactic acid 0.1
Tremoist-TP (Nippon Fine Chemical) 0.01
Ethanol 10.0
Menthol 0.1
Menthyl glyceryl ether 0.15
Panthenyl ethyl ether 0.2
Camphor 0.1
Cordyceps sinensis extract 1.0
Swertia japonica extract 1.0
Loquat leaf extract 1.0
Hydrolyzed hyaluronic acid 0.02
Sodium cyclic lysophosphatidic acid 0.001
Chili pepper extract 0.01
Betaine 0.3
Trehalose 0.2
Cymene-5-ol 0.1
Tocopherol acetate 0.05
β-Glycyrrhetinic acid 0.05
Purified water, an amount that totals 100.
(Preparation method)
All ingredients were weighed into a container and stirred with a paddle at room temperature to obtain a homogeneous liquid.

Example 21 Whitening emulsion Ingredients Amount (wt%)
---------------------------------------------------------------------------
Part A Plandool-DP (Nippon Fine Chemical) 1.0
Cetyl ethylhexanoate (Nippon Seika) 10.0
Cetanol 1.2
Dimethicone 100 cs 3.0
Myristyl alcohol 2.0
Oleyl alcohol 1.0
Part B: Stearoxyhydroxypropylmethylcellulose 0.1
Xanthan gum 0.1
Sodium citrate (appropriate amount), purified water (20 ml)
C part Phytocompo-PP (Nippon Fine Chemical) 1.0
Glycerin 8.0
Part D: 3-O-ethyl ascorbic acid (Nippon Seika) 0.5
Tranexamic acid (Nippon Seika) 2.0
Nicotinamide 5.0
Glycerin solution of β-type zinc lysophosphatidicate from Example 3 1.0
Purified water 5.0
Section E: Phenoxyethanol 0.2
Methylparaben 0.15
Phytic acid 0.5
Purified water, an amount that totals 100.
(Preparation method)
Parts A and E were heated to approximately 70°C and dissolved uniformly. Part B was stirred to make a viscous liquid. Part C was heated to approximately 70°C and dispersed uniformly. Part A was added to Part C while stirring in a homodisperser, and then Part E was added while stirring. Parts D and B were added at approximately 50°C, stirred to mix uniformly, and the pH was adjusted to 6.5-7.0 with sodium citrate.

Example 22 Emulsion Component Amount (wt%)
------------------------------------------------------------------
Part A: Glycerin 3.0
Diglycerin 1.0
BG 5.0
Phytocompo-C (Nippon Fine Chemical) 1.5
Part B: Triethylhexanoin (Nippon Seika) 3.0
LUSPLAN SR-DM4 (Nippon Seika) 0.5
Hydrogenated polyisobutene 3.5
Isododecane 1.5
Cetostearyl alcohol 1.0
Alkali alcohol 0.1
Jojoba alcohol 3.0
Kimyl alcohol 0.3
Cerakill alcohol 0.1
Hexyldecanol 0.5
Part C (Hydroxyethyl Acrylate/Sodium Acryloyldimethyl Taurate) Copolymer
0.2
Tremoist-TP (Nippon Fine Chemical) 0.03
Carbomer 0.1
Potassium hydroxide 0.2
Purified water 30.0
D part Neosolue-AquaS (Nippon Fine Chemical) 0.5
Polyquaternium-51 1.0
Glycerin solution of β-type zinc lysophosphatidicate from Example 3 1.0
Tranexamic acid (Nippon Seika) 2.0
Nicotinamide 5.0
Methylparaben 0.15
Purified water, an amount that totals 100.
(Preparation method)
Parts A, B, and D were mixed separately and heated to approximately 70°C to uniformly dissolve and disperse. Part C was mixed in and stirred to form a viscous liquid. Part B was added to Part A while stirring in a homodisperser, then Part D was added and emulsified. The mixture was cooled to approximately 50°C, Part C was added, stirred, and cooled to approximately 40°C.

Example 23: Skincare Cream - Ingredients and Amount (Weight %)
------------------------------------------------------------------
Part A: Glycerin solution of β-type zinc lysophosphatidicate from Example 3 1.0
Sodium cyclic lysophosphatidic acid 0.01
Glycerin 9.0
DPG 5.0
Tripropylene glycol 2.0
Sucrose stearate 1.5
Part B (C13-15) Alkanes 8.0
Vaseline 10.0
Pentaerythrityl tetraisostearate 5.0
Astaxanthin 0.01
Cetyl PG hydroxyethyl palmitamide 0.05
Dipentaerythrityl hexahydroxystearate 1.0
Stearyl glycyrrhetinate 0.05
Part C: Carbomer 0.1
Potassium hydroxide 0.07
Xanthan gum 0.1
Purified water 10.0
Part D: Phenoxyethanol 0.4
Ethylhexylglycerin 0.2
Methylparaben 0.05
Inulin-SC (Nippon Fine Chemical) 1.0
Nicotinamide 5.0
Purified water, an amount that totals 100.
(Preparation method)
Parts A, B, and D were mixed separately and heated to approximately 70°C to uniformly dissolve and disperse. Part C was mixed in and stirred to form a viscous liquid. Part B was added to Part A while stirring in a homodisperser, then Part D was added and emulsified. The mixture was cooled to approximately 50°C, Part C was added, stirred, and cooled to approximately 40°C.

Example 24 Skincare Cream Ingredients Amount (weight %)
------------------------------------------------------------------
Part A: Sugar Squalane 10.0
Stearic acid 1.0
Plandool-ISS (Nippon Fine Chemical) 1.0
Macadamia nut oil 3.0
Hydrogenated rapeseed alcohol 2.0
Cetearyl olivate 1.0
Olive oil fatty acid sorbitan 0.8
Polyglyceryl-10 oleate 1.0
Part B: Acrylic acid/alkyl methacrylate copolymer 0.1
Potassium hydroxide 0.07
(Acryloyldimethyltaurate ammonium/
Beheneth-25 methacrylate crosspolymer 0.2
Tremoist-SL (Nippon Seika) 1.0
Purified water 20.0
Hydrolyzed polyγ-glutamate K 0.1
Sodium polyglutamate 0.1
Oligopeptide-24 0.05
Part C PrimeLipid-PI (Nippon Fine Chemical) 1.0
0.5g of glycerin solution of β-type aluminum lysophosphatidicate from Example 2
Propanediol 10.0
PEG-8 5.0
PEG-2M 2.0
Glyceryl caprylate 0.8
Purified water, an amount that totals 100.
(Preparation method)
Parts A and C were mixed separately and heated to approximately 70°C to dissolve and disperse uniformly. Part B was mixed and stirred to form a viscous liquid. Part C was added to Part A while stirring with a homomixer and emulsified. After cooling to approximately 50°C, Part B was added and stirred, and the mixture was cooled to approximately 40°C.

Example 25 Skincare Cream Ingredients Amount (weight %)
------------------------------------------------------------------
Part A Plandool-MAS (Nippon Fine Chemical) 2.0
Plandool-LG1 (Nippon Seika) 1.0
Paraffin wax 3.0
Shea butter 3.0
Squalane 8.0
Cetanol 1.8
Hydrogenated Cocoglycerides 0.8
Glyceryl stearate 1.0
Behenyl alcohol 1.5
Sorbitan stearate 1.0
Polyglyceryl-10 laurate 1.0
PEG-60 Glyceryl Isostearate 1.0
Methyl glucose sesquistearate 1.5
Part B: Xanthan gum 0.1
Hydroxyethylcellulose 0.1
Crystalline cellulose powder 0.3
Stearoxyhydroxypropylmethylcellulose 0.1
Tranexamic acid (Nippon Seika) 4.0
Purified water 20.0
Part C: Glycerin 8.0
DPG 5.0
Sorbitol 2.0
2.5g of glycerin solution of β-type aluminum lysophosphatidicate from Example 2
Neosolue-Aqualio (Nippon Seika) 1.0
Methylparaben 0.15
Purified water, an amount that totals 100.
(Preparation method)
Parts A and C were mixed separately and heated to approximately 70°C to dissolve and disperse uniformly. Part B was mixed and stirred to form a viscous liquid. Part C was added to Part A while stirring with a homomixer and emulsified. After cooling to approximately 50°C, Part B was added and stirred, and the mixture was cooled to approximately 40°C.

Example 26 Skincare Cream Ingredients Amount (weight %)
------------------------------------------------------------------
Part A: Glycerin 12.0
BG 3.0
Phytocompo-PP (Nippon Fine Chemical) 2.5
Part B: Olive fruit oil 3.0
Olive oil 1.5
Shea butter 1.0
Pentaerythrityl tetraethylhexanoate (Nippon Seika) 3.0
Sucrose stearate 0.8
Cetearyl glucoside 1.2
Behenyl alcohol 1.5
Ascorbyl tetrahexyldecanoate 7.0
Isopropyl lauroyl sarcosinate 2.0
Hydrogenated Cocoglycerides 3.0
Cetanol 2.5
Sorbitan stearate 0.8
Part C: Xanthan gum 0.05
Tremoist-SL (Nippon Seika) 1.0
Tuberose polysaccharide 0.01
Water-soluble collagen 0.05
Hydrolyzed collagen 0.5
Sodium pyrosulfite 0.03
3.5 glycerin solution of β-type aluminum lysophosphatidicate from Example 2
Arbutin (Nippon Seika) 1.0
Tranexamic acid (Nippon Seika) 1.0
Purified water 10.0
D part Neosolue-Aqulio (Nippon Fine Chemical) 1.0
Propanediol 3.0
Methylparaben 0.1
Glyceryl caprylate 1.0
Purified water, an amount that totals 100.
(Preparation method)
Parts A, B, and D were mixed separately and heated to approximately 70°C to uniformly dissolve and disperse. Part C was mixed in and stirred to form a viscous liquid. Part B was added to Part A while stirring in a homodisperser, then Part D was added and emulsified. The mixture was cooled to approximately 50°C, Part C was added, stirred, and cooled to approximately 40°C.

Example 27 Skincare Cream Ingredients Amount (weight %)
--------------------------------------------------
Part A Neosolue-DiSM (Nippon Fine Chemical) 5.0
Jojoba oil 2.0
Plandool-H (Nippon Fine Chemical) 1.0
Neosolue-MCT (Nippon Seika) 3.0
LUSPLAN DD-DHR (Nippon Seika) 1.0
Plandool-SUN (Nippon Fine Chemical) 1.3
Propylene glycol stearate 0.6
Squalane 3.0
Behenyl alcohol 2.0
Liquid isoparaffin 0.5
Carnauba wax 0.3
Corn oil 0.3
Rapeseed oil 1.0
Sunflower oil 1.0
wheat germ oil 1.0
Flaxseed oil 0.1
Cottonseed oil 0.1
Soybean oil 0.1
Shea butter 0.5
Stigmasterol 1.0
Stigma 1.0
Dihydrocholesterol 0.1
Lanosterol 0.1
Dihydrolanosterol 0.1
Cholesteryl nonanoate 0.1
Cholesteryl stearate 0.1
Cholesteryl isostearate 1.0
Cholesteryl oleate 0.1
12-Cholesteryl hydroxystearate 0.1
Long-chain branched fatty acid cholesteryl 0.3
Octyldodecyl myristate 1.0
Octyldodecyl isostearate 1.0
Dimer dilinoleic acid hydrogenated castor oil 1.0
Hydroxyalkyl dimer dilinoleyl ether 1.0
Tetra(hydroxystearic acid/isostearate)dipentaerythrityl
0.5
Rice bran oil fatty acid phytosteryl 0.5
Phenylentrimethicone 1.0
Diphenyldimethicone 1.0
Methylhydrogenpolysiloxane 1.0
Polyglyceryl-3 polydimethylsiloxyethyl dimethicone 0.5
Dimethicone 50 cs 0.3
Polyoxyethylene methylpolysiloxane copolymer 1.0
Tocopherol ferulate 0.1
Tocopherol phosphate 0.1
Tocotrienol 0.1
Tannin 0.01
Sesamin 0.01
Proanthocyanidin 0.01
Glabridin 0.01
Grabren 0.01
Liquiiritin 0.01
Isoliqueritin 0.01
Lactoferrin 0.01
Gingerol 0.01
Gingerol 0.01
Part B (Acryloyldimethyltaurine/Beheneth-25 Methacrylate) Copolymer
0.2
Crystalline cellulose 0.1
Gellan gum 0.1
Carboxyvinyl polymer 0.1
K hydroxide 0.08
Purified water 20.0
Part C Phytocompo-PP (Nippon Fine Chemical) 1.0
Glycerin solution of β-type zinc lysophosphatidicate from Example 3 0.5
Polyglyceryl-10 stearate 0.5
Glycerin 7.0
DPG 7.0
Part D: Citric Acid 0.07
Sodium citrate (appropriate amount), EDTA-2Na (0.05%)
Pentasodium pentetate 0.03
Phenoxyethanol 0.4
Purified water, an amount that totals 100.
(Preparation method)
Part A was mixed and heated to approximately 70°C to dissolve uniformly. Part B was mixed and stirred to form a viscous liquid. Part C was mixed and heated to approximately 70°C to disperse uniformly. Part D was mixed and heated to approximately 70°C to dissolve uniformly. Part A was added to Part C while stirring in a homogenizer, then Part D was added and emulsified. After cooling to approximately 50°C, Part B was added and stirred to dissolve uniformly.

Example 28: Skincare Cream - Ingredients and Amount (Weight %)
---------------------------------------------------------------------------
Part A Plandool-G (Nippon Fine Chemical) 1.0
Neosolue-Aqualio (Nippon Seika) 1.5
Diethylhexyl sebacate (Nippon Seika) 8.0
Diisopropyl sebacate (Nippon Seika) 2.0
Theobroma grandiflorum seed butter 3.0
Batyl isostearate 2.0
Shea butter 3.0
(Dimethicone/Vinyl Dimethicone) Crosspolymer 0.3
(Vinyl dimethicone/Lauryl dimethicone) crosspolymer 0.5
(Dimethicone/PEG-10/15) Crosspolymer 0.5
(PEG-15/Lauryl Dimethicone) Crosspolymer 0.2
(Alkyl acrylate/dimethicone) copolymer 0.1
Isostearyl pivalate 0.1
Pentaerythrityl tetraethylhexanoate (Nippon Seika) 0.1
Stearyl alcohol 3.5
Cetanol 1.3
Coconut fatty acid sucrose 1.0
Polyglyceryl-3 methylglucose distearate 0.8
Triglycerides (C10-18) 3.0
Squalane 3.0
Dimethicone 100 cs 1.0
Tocopherol 0.1
Ascorbyl tetrahexyldecanoate 8.0
Tocopheryl ascorbyl phosphate 2.0
Placenta extract 1.0
Oryzanol 0.3
Phytosphingosine 0.0001
Ubiquinone 0.03
Carotene 0.05
Lycopene 0.01
Astaxanthin 0.01
Lutein 0.01
Fullerene 0.001
Peanut oil 0.1
Rice bran oil 1.0
Hydrogenated castor oil 0.3
Jojoba oil 2.0
Orange roughy oil 1.0
Liquid lanolin (Nippon Seika) 1.0
Lanolin (Nippon Seika) 1.0
Polyoxyethylene lanolin 1.0
Lanolin alcohol (Nippon Seika) 0.3
Alcoholic lanolin acetate 0.1
Cholesteryl acetate 0.1
Octocrylene 0.5
Sorbitan sesquistearate 1.2
Part B Tremoist-TP (Nippon Fine Chemical) 0.05
Water-soluble collagen 0.05
Hydrolyzed collagen 0.5
Glutathione 0.3
Arbutin (Nippon Seika) 3.0
Nicotinamide 5.0
Part C: Glycerin solution of β-type zinc lysophosphatidicate from Example 3 1.0
Propanediol 10.0
PPG-9 Diglyceryl 2.0
Diglycerin 1.0
Sodium pyrosulfite 0.1
Imidazolinium urea 0.1
Polyvinylpyrrolidone 0.1
Pullulan 0.1
Polyvinyl alcohol 0.1
Dehydroacetic acid 0.1
PEG-32 1.0
Polyglycerin-10 1.0
Pentasodium pentetate 0.05
Phenoxyethanol 0.4
1,2-pentanediol 2.0
Succinic acid 0.05
Sodium succinate (appropriate amount) Purified water (total amount equal to 100)
(Preparation method)
Part A was heated to approximately 70°C and dissolved uniformly. Part B was homogenized using some purified water. Part C was heated to approximately 70°C and dispersed. While stirring with a homomixer at approximately 70°C, Part A was gradually added to Part C and emulsified. After cooling to approximately 40°C, Part B was added and mixed uniformly, and the pH was adjusted to 6.5-7.0 with sodium succinate.

Example 29 Emulsion Component Amount (wt%)
--------------------------------------------------
Part A Phytocompo-SP (Nippon Fine Chemical) 10.0
Lysolecithin (Nippon Seika) 0.1
Glycerin solution of β-type zinc lysophosphatidicate from Example 3 3.5
Part B: Squalane 4.0
Neosolue-MCT (Nippon Seika) 4.0
α-olefin oligomer 2.5
Dimethicone 5cs 3.5
Cetanol 1.5
Glyceryl stearate 1.0
Part C: Hydroxyproline 0.05
Citric acid 0.01
Sodium citrate 0.09
Arbutin (Nippon Seika) 3.0
Phenoxyethanol 0.3
Methylparaben 0.1
Acrylic acid/alkyl methacrylate copolymer 0.1
K hydroxide 0.1
Purified water, an amount that totals 100.
(Preparation method)
Parts A, B, and C were each taken and heated to approximately 70°C, then mixed uniformly. Part B was gradually added to part A while stirring with a homodisperser, and then part C was added at approximately 70°C and emulsified. After that, it was cooled to approximately 40°C.

Example 30 Cleansing Gel Ingredients Amount (weight %)
--------------------------------------------------
Part A: Glycerin solution of β-type zinc lysophosphatidicate from Example 3 2.5
1,2-pentanediol 1.0
Cetyl ethylhexanoate (Nippon Seika) 10.0
Plandool-S (Nippon Fine Chemical) 1.0
Dihydrocholeth-30 (Nippon Seika) 2.0
LUSPLAN DD-IS (Nippon Fine Chemical) 8.0
PEG-25 Hydrogenated Castor Oil 20.0
Octyldodeceth-20 15.0
Glycerin 16.0
BG 5.0
Part B: Phenoxyethanol 0.5
Purified water, an amount that totals 100.
(Preparation method)
Part A was heated to approximately 80°C and dissolved. Part B was heated to approximately 80°C. Part B was gradually added to Part A while stirring, and after mixing, it was cooled to 40°C.

Example 31 Cleansing Cream Ingredients Amount (weight %)
--------------------------------------------------
Part A Plandool-LG2 (Nippon Fine Chemical) 1.0
Neosolue-Aqualio (Nippon Seika) 1.0
Ceresin 6.0
0.5g of glycerin solution of β-type zinc lysophosphatidicate from Example 3
PEG-12 isostearate 3.0
Sorbitan sesquioleate 1.5
Polyoxyethylene sorbitan oleate 0.3
Polyglyceryl-10 laurate 0.3
Microcrystalline wax 2.0
Tocopherol 0.05
Part B Neosolue-Aqua (Nippon Fine Chemical) 0.5
DPG 5.0
EDTA trisodium 0.02
Phenoxyethanol 0.5
Purified water, an amount that totals 100.
(Preparation method)
Part A was heated to approximately 80°C and dissolved. Part B was heated to approximately 80°C. Part B was gradually added to Part A while stirring, and after mixing, it was cooled to 40°C.

Example 32 Facial Cleansing Foam Ingredients Amount (weight %)
--------------------------------------------------
Part A: Glycerin solution of β-type zinc lysophosphatidicate from Example 3 1.0
(Coconut fatty acid/hydrogenated beef tallow fatty acid) sodium glutamate 30.0
Cocoyl glycine K 5.0
Plandool-LG2 (Nippon Seika) 0.2
Lauric acid diethanolamide 3.0
Tocopherol 0.1
PEG-8 5.0
PEG-32 10.0
Glycerin 14.0
Part B: Glyceryl Caprylate 1.0
Hexanediol 1.0
Polyquaternium-51 1.0
Tremoist-SL (Nippon Seika) 0.5
Crystalline cellulose 0.3
Polyquaternium-7 0.8
Purified water, an amount that totals 100.
(Preparation method)
Part A was heated to approximately 80°C and dissolved. Part B was heated to approximately 80°C. Part B was gradually added to Part A while stirring, and after mixing, it was cooled to 40°C.

Example 33 Body Shampoo Ingredients Amount (weight %)
--------------------------------------------------
Glycerin solution of β-type zinc lysophosphatidicate from Example 3 1.0
Sodium Cocoyl Methyl Taurate 10.0
Sodium Lauroyl Hydrolyzed Silk 6.0
Sodium lauroyl methylalanine 10.0
Sodium cocoamphoacetate (30%) 4.0
Cocamidopropyl betaine (30%) 10.0
Sodium olefin (C14-16) sulfonate 5.0
Polyquaternium-10 1.3
Guar hydroxypropyltrimonium chloride 0.8
Sodium acetylated hyaluronate 0.02
Cocamide DEA 3.0
Glycerin 5.0
Methylparaben 0.2
Purified water, an amount that totals 100.
(Preparation method)
All ingredients were heated to approximately 80°C and stirred until uniform.

Example 34 Non-silicone shampoo Ingredients Amount (weight %)
--------------------------------------------------
Glycerin solution of β-type zinc lysophosphatidicate from Example 3 1.0
Plandool-LG2 (Nippon Seika) 0.03
Neosolue-AquaS (Nippon Fine Chemical) 0.1
Tremoist-SL (Nippon Seika) 0.5
Sodium laureth-4 carboxylate (28%) 10.0
Laureth-6 carboxylic acid 4.0
Cocamidopropyl betaine (30%) 10.0
Sodium Lauroyl Methylalanine (30%) 5.0
Cocamide methyl MEA 3.0
PEG-7 glyceryl coconut oil fatty acid 5.0
0.5g of 1% sodium hydroxide solution
Polyquaternium-10 0.8
Glycol distearate 0.5
Polyquaternium-7 0.5
EDTA-2Na 0.05
Phenoxyethanol 0.4
Sodium benzoate 0.2
Purified water, an amount that totals 100.
(Preparation method)
All ingredients were heated to approximately 80°C and stirred until uniform.

Example 35 Hand soap Ingredients Amount (weight %)
--------------------------------------------------
Part A: Sodium Cocoyl Isethionate 1.0
Glycerin 50.0
Glycerin solution of β-type zinc lysophosphatidicate from Example 3 1.0
Part B: Sodium Lauroyl Sarcosinate 12.0
Sodium myristoylmethyltaurate 2.0
Polyglyceryl-6 laurate 2.0
Coconut oil fatty acid diethanolamide 2.0
PEG-7 Coconut Oil Fatty Acid Glyceryl 2.0
Sorbitol 8.0
Hydrolyzed conchiolin 0.1
1,3-Butylene glycol 8.0
Phenoxyethanol 0.8
Ethanol 3.0
Purified water, an amount that totals 100.
(Preparation method)
Part A was heated to approximately 80°C and melted. Part B was added to Part A, heated to approximately 80°C, and after uniform melting, it was cooled.

Example 36 Leave-in hair treatment Ingredients Amount (weight %)
------------------------------------------------------------------
Part A: Glycerin solution of β-type zinc lysophosphatidicate from Example 3 1.0
Polyquaternium-37 2.0
Squalane 2.0
PPG-3 Caprylyl Ether 2.0
Microcrystalline wax 0.1
Lanolin alcohol 0.2
Montan Wax 0.1
Polyethylene wax 0.1
Woodrow 0.2
Ceresin 0.1
PG dicaprate 1.0
Almond oil 0.5
Ethylhexyl ethylhexanoate 1.0
Candelilla wax extract 0.1
Octyldodecyl erucate 4.5
Tocopherol acetate 0.02
Elcalactone MCT (Nippon Seika) 2.0
Dipentaerythrityl tripolyhydroxystearate 1.5
PPG-5 Phytosteryl 0.5
Glycerin 4.0
Sorbitol 2.0
Phenoxyethanol 0.5
Part B: Hydrolyzed hyaluronic acid 0.1
Panthenol 0.1
Hydroxypropyltrimonium hyaluronate 0.01
Polyquaternium-11 0.2
Glycosyltrehalose 0.1
Glyceryl glucoside 0.3
Arginine 0.1
Part C: Purified water (total amount to 100), Hydroxypropyl starch phosphate 1.0
---------------------------------------------------------------------------
(Preparation method)
Part C was uniformly dispersed and heated to approximately 80°C. Next, Part A was heated to approximately 80°C and dissolved. Part A was added to Part C while stirring, and after uniform mixing, it was cooled to approximately 40°C. Then, Part B was added to each and mixed uniformly.

Example 37 Leave-in scalp/hair treatment Ingredients Amount (weight %)
---------------------------------------------------------------------------
Part A: Glycerin solution of β-type zinc lysophosphatidicate from Example 3 1.5
Neosolue-Aqualio (Nippon Seika) 1.0
Ethanol 40.0
Glycyrrhetinic acid 0.02
Elcalactone DES (Nippon Seika) 1.5
PEG/PPG-20/20 Dimethicone 0.2
PEG-12 Dimethicone 0.4
Hydrogenated retinol 0.1
Pyridoxine trishexyldecanoate 0.05
Bisglyceryl ascorbate 0.3
Hexyl 3-glyceryl ascorbate 0.3
Part B: Triethanolamine 0.1
Purified water (total amount to 100) (Acrylates/C10-30 alkyl acrylate) crosspolymer 0.4
Carbomer 0.05
Tremoist-SL (Nippon Seika) 1.0
(Acryloyldimethyltaurate Ammonium/VP) Copolymer 0.05
(Acryloyldimethyltaurate ammonium/
Beheneth-25 methacrylate crosspolymer 0.1
Hydroxypropyl chitosan 0.1
Methylparaben 0.1
Phenoxyethanol 0.2
Part C: 3-O-ethyl ascorbic acid (Nippon Seika) 0.3
Nicotinamide 0.3
Pyridoxine hydrochloride 0.1
Caffeine 0.1
Glucosyltrehalose 0.1
Purified water 10.0
---------------------------------------------------------------------------
(Preparation method)
Part A was heated to approximately 50°C and dissolved. Next, Part B was uniformly dispersed to form a viscous liquid. Part A was added to Part B while stirring and mixed uniformly. Then Part C was added and mixed uniformly.

Example 38 Shampoo Ingredients Amount (weight %)
--------------------------------------------------
Part A: Glycerin solution of β-type zinc lysophosphatidicate from Example 3.
PPG-3 Caprylyl Ether 0.2
Ammonium laureth sulfate 5.0
Sodium laureth sulfate (25%) 10.0
Lauryl hydroxysultaine (30%) 10.0
Potassium laurate 1.0
Glycol distearate 0.5
Toluene sulfonic acid 0.3
Stearoxypropyldimethylamine 0.5
PPG-17 0.3
Dimethicone 0.1
PEG-9 Dimethicone 0.1
Amodimethicone 0.1
Diethylhexyl sebacate (Nippon Seika) 1.0
Neopentyl glycol diethylhexanoate 0.4
Lanolin fatty acid 0.3
Isodecyl glyceryl ether 0.4
Miconazole nitrate 0.75
Cocamide MEA 1.0
Laureth-4 0.3
Laureth-16 0.2
Steerless-6 0.2
Phenoxyethanol 0.3
Part B: Malic acid 0.1
Methylparaben 0.2
Phosphate 0.03
Sodium benzoate 0.3
Arginine 0.4
Purified water, amount C to make a total of 100; Polyquaternium-10, 0.2
Guar hydroxypropyltrimonium chloride 0.1
Tremoist-SL (Nippon Seika) 3.0
Purified water 6.7
--------------------------------------------------
(Preparation method)
Part A was uniformly mixed at approximately 80°C. Part B, which had been set aside, was heated to approximately 60°C and made uniform. Part B was gradually added to Part A while stirring, and after being uniformly mixed, it was cooled to approximately 50°C. Part C was then added and uniformly mixed.

Example 39 Leave-on Hair Treatment Ingredients Amount (weight %)
--------------------------------------------------
Part A: Glycerin solution of β-type zinc lysophosphatidicate from Example 3 1.0
Neosolue-Aqualio (Nippon Seika) 2.0
RepairLipid-DSL (Nippon Fine Chemical) 1.0
Cetanol 3.8
Caprylyl glucoside (50%) 1.5
Glycerin 4.0
Phenoxyethanol 0.5
Part B: Ethanol 5.0
Part C: Polyquaternium-6 0.6
Polyquaternium-7 0.4
Polyquaternium-39 0.5
Purified water, an amount that totals 100.
(Preparation method)
Part C was heated to approximately 80°C and dissolved. Next, Part A was heated to approximately 80°C and dissolved. Part A was added to Part C while stirring, and after uniform mixing, it was cooled to approximately 40°C. Then, Part B was added and uniformly mixed.

Example 40 Lipstick Ingredients Amount (wt%)
--------------------------------------------------
0.5g of glycerin solution of β-type zinc lysophosphatidicate from Example 3
LUSPLAN SR-DM4 (Nippon Seika) 7.0
Hydrogenated polyisobutene 5.0
Triethylhexanoin (Nippon Seika) 10.0
Neosolue-MCT (Nippon Seika) Amount that totals 100 Dialkyl carbonate (C14, 15) 3.0
Dextrin palmitate 0.9
Sodium stearoyl lactate 0.9
Cetyl ethylhexanoate (Nippon Seika) 24.0
Dimethicone 50 cs 5.0
Plandool-MAS (Nippon Seika) 2.0
Ceresin 8.5
Candelilla Raw 4.0
Sorbitan sesquioleate 0.15
Hydrogen dimethicone 2.0
Ethanol 0.1
Tocopherol 0.5
Nylon-12 2.0
(Ethylene/Propylene) Copolymer 0.5
Barium sulfate 1.0
Iron oxide 2.0
Mica 2.0
Titanium dioxide 1.0
--------------------------------------------------
(Preparation method)
After uniformly heating, stirring, and mixing all the ingredients, the mixture was filled into molds and rapidly cooled.

Example 41 Lip balm Ingredients Amount (weight %)
--------------------------------------------------
Plandool-H (Nippon Fine Chemical) 10.0
Plandol-LG3 (Nippon Seika) 5.0
Polyglyceryl-2 diisostearate 15.0
Glycerin solution of β-type zinc lysophosphatidicate from Example 3 4.0
Squalane: Amount that makes a total of 100 12-Hydroxystearic Acid: 5.0
Silylated silica 3.0
Menthol 0.5
Fragrance: appropriate amount Antioxidant: appropriate amount --------------------------------------------------
(Preparation method)
All ingredients were heated to approximately 90°C, mixed uniformly, and then cooled.

Example 42 Foundation Ingredients and Amount (Weight %)
--------------------------------------------------
Plandool-S (Nippon Fine Chemical) 1.0
Plandool-G (Nippon Fine Chemical) 0.1
Plandool-SUN (Nippon Fine Chemical) 0.1
Plandool-MAS (Nippon Seika) 0.1
Plandool-ISS (Nippon Fine Chemical) 0.1
Glycerin solution of β-type zinc lysophosphatidicate from Example 3 2.0
Cyclomethicone 3.5
Trimethylsiloxysilicate 1.5
Talc 24.0
Iron oxide 1.9
Titanium dioxide 20.0
Tocopherol 0.1
Ethylhexyl methoxycinnamate 1.0
Neosolue-AquaS (Nippon Fine Chemical) 0.4
Phenoxyethanol 0.4
The amount of mica that totals 100 --------------------------------------------------
(Preparation method)
All ingredients were stirred and mixed uniformly before being molded.

Example 43: Solid powder foundation. Ingredients and amount (weight %).
--------------------------------------------------
Part A Plandool-H (Nippon Fine Chemical) 2.0
YOFCO MAC (Nippon Seika) 0.1
Plandool-LG1 (Nippon Seika) 0.1
Plandool-LG2 (Nippon Seika) 0.1
Plandool-LG4 (Nippon Seika) 0.1
LUSPLAN PI-DA (Nippon Fine Chemical) 3.0
Cetyl ethylhexanoate (Nippon Seika) 3.0
Glycerin solution of β-type zinc lysophosphatidicate from Example 3 3.0
Squalane 1.6
Part B: Lecithin-treated sericite 20.0
Boron nitride 10.0
Mica 3.0
Silica 2.0
Dimethicone 3.0
Nylon-12 3.0
Talc 10.0
Titanium dioxide 10.0
The amount of iron oxide that makes up 100 -------------------------------------------------
(Preparation method)
Part A was heated and mixed. Part B was placed in a separate container and mixed and dispersed. Part A was added to Part B, and after uniform mixing, it was molded.

Example 44 Liquid Foundation Ingredients Amount (weight %)
--------------------------------------------------
Part A: Glycerin solution of β-type zinc lysophosphatidicate from Example 3 7.0
PrimeLipid-PI (Nippon Fine Chemical) 1.0
Octyltriazone 1.5
Ethylhexyl methoxycinnamate 1.0
Quaternium-18 hectorite 0.5
Part B: Cyclomethicone 25.0
Polyether-modified silicone mixture 5.0
(Manufactured by Toray Dow Corning Silicone Co., Ltd., BY22-008M)
Polyglyceryl-2 isostearate 1.0
Titanium oxide/iron oxide mixture 12.5
Mica 6.0
Part C: Glycerin 5.0
Neosolue-AquaS (Nippon Fine Chemical) 0.4
Methylparaben 0.2
Tranexamic acid (Nippon Seika) 2.0
Purified water, an amount that totals 100.
(Preparation method)
Part A was heated to approximately 80°C and thoroughly dispersed. Part B, also heated to approximately 80°C, was added to this, and then Part C, further heated to approximately 80°C, was added. The mixture was emulsified and dispersed using a homogenizer, and then stirred and cooled to room temperature.

Example 45 Foundation Ingredients and Amount (Weight %)
--------------------------------------------------
Part A: Glycerin solution of β-type zinc lysophosphatidicate from Example 3 1.0
Isododecane 10.0
Neosolue-MCT (Nippon Seika) 4.0
Ethylhexyl Methoxycinnamate 3.0
Plandool-SUN (Nippon Fine Chemical) 1.0
Plandool-LG2 (Nippon Seika) 1.0
Plandool-LG4 (Nippon Seika) 1.0
Vaseline 1.0
Isotridecyl isononanoate 2.0
Ascorbyl tetrahexyldecanoate 0.1
Dextrin palmitate 0.3
Sorbitan isostearate 1.5
Tribehenin 0.5
(Butyl acrylate/glycol dimethacrylate) crosspolymer, silica,
(Methyl methacrylate/glycol dimethacrylate) crosspolymer mixture
2.0
Boron nitride 1.0
Polysorbate 20 2.0
PEG-60 Hydrogenated Castor Oil 1.0
Disteardimonium hectorite (20%) 2.5
Polypropylsilsesquioxane and cyclopentasiloxane mixture
1.0
Mica 15.0
Talc 4.0
Zinc oxide 5.0
Titanium dioxide 10.0
Iron oxide 1.5
Part B: Water, total amount to make 100, DPG 4.0
Maltitol (75% solution) 1.0
Neosolue-AquaS (Nippon Fine Chemical) 0.4
Sodium chloride 1.0
BG 1.0
Tremoist-SL (Nippon Seika) 1.0
Ethanol 0.5
Phenoxyethanol 0.3
--------------------------------------------------
(Preparation method)
Part A was heated to approximately 70°C and thoroughly stirred to ensure uniform dispersion. Part B was heated to approximately 70°C and made uniform, then Part B was added to Part A, stirred at approximately 70°C to emulsify, and cooled to approximately 40°C.

Example 46 Sunscreen Cosmetic Ingredients Amount (by weight)
--------------------------------------------------
Part A: FINEX-33W (Sakai Chemical Industry) 5.0
STR-100W (Sakai Chemical Industry) 5.0
Purified water, amount to make a total of 100, BG 7.0
Disodium edetate 0.05
Triethanolamine 1.0
Part B: Oxybenzone 3.0
Octyl paramethoxycinnamate 5.0
t-Butylmethoxybenzoylmethane 3.0
PrimeLipid-PI (Nippon Fine Chemical) 1.0
Glycerin solution of β-type zinc lysophosphatidicate from Example 3 3.0
Diethylhexyl sebacate (Nippon Seika) 8.0
Plandool-H (Nippon Fine Chemical) 2.0
Plandool-SUN (Nippon Fine Chemical) 2.0
Plandool-MAS (Nippon Seika) 0.1
Plandool-LG1 (Nippon Seika) 0.1
Plandool-LG2 (Nippon Seika) 0.1
Plandool-LG3 (Nippon Seika) 0.1
Plandool-LG4 (Nippon Seika) 0.1
LUSPLAN PI-DA (Nippon Fine Chemical) 3.0
Cetyl ethylhexanoate (Nippon Seika) 3.0
Diisopropyl sebacate (Nippon Seika) 5.0
Dimethicone 2cs 5.0
Sucrose stearate 1.5
Polyglyceryl-10 stearate 2.0
Stearyl alcohol 3.0
Batyl alcohol 1.0
Stearic acid 3.0
Glyceryl monostearate 3.0
Ethyl polyacrylate 1.0
Phenoxyethanol 0.5
--------------------------------------------------
(Preparation method)
Part A was heated to approximately 80°C and thoroughly dispersed. Part B, also heated to approximately 80°C, was added to this, and the mixture was emulsified and dispersed using a homogenizer, then stirred and cooled to room temperature.

Example 47 Sunscreen Cosmetic Ingredients Amount (by weight)
--------------------------------------------------
Part A BG 10.0
Glycerin 9.0
Phytocompo-PP (Nippon Fine Chemical) 1.0
Octocrylene 4.0
Octyl salicylate 4.0
Diethylamino hydroxybenzoyl hexyl benzoate 2.25
t-Butyl methoxydibenzoylmethane 1.0
Diethylhexyl sebacate (Nippon Seika) 3.0
Pentaerythrityl tetraethylhexanoate (Nippon Seika) 2.0
Diisopropyl sebacate (Nippon Seika) 1.0
Behenyl alcohol 2.0
Cetearyl alcohol 2.0
Plandool-MAS (Nippon Seika) 1.0
Tocopherol 0.05
Part B Neosolue-AquaS (Nippon Fine Chemical) 1.0
Methylparaben (appropriate amount), Water (total amount equal to 100), C parts Carbomer (2%) 5.0
Tremoist-SL (Nippon Seika) 10.0
DIS-AB-10W (Sakai Chemical Industry) 5.0
0.2g of glycerin solution of β-type zinc lysophosphatidicate from Example 3
--------------------------------------------------
(Preparation method)
Heat and dissolve parts A and B to approximately 70°C. Gradually add part B to part A and emulsify. Cool while stirring, and mix in part C at 45°C.

Example 48 Cosmetic Oil Ingredients Amount (weight %)
--------------------------------------------------
Neosolue-DiSM (Nippon Seika) Amount that totals 100 2.0g of glycerin solution of β-type zinc lysophosphatidicate from Example 3
PrimeLipid-PI (Nippon Fine Chemical) 1.0
Octyldodecanol 40.0
Plandool-LG2 (Nippon Seika) 3.0
Ceramide 2 1.0
Ceramide 5 1.0
Cholesterol 5.0
Appropriate amount of corrosive agent --------------------------------------------------
(Preparation method)
All ingredients were stirred and mixed at approximately 90°C, and then allowed to cool.

In the above formulation, the details of the ingredients listed under the product name are as follows:

Plandool-H: Dimer dilinoleate (phytosteryl/isostearyl/cetyl/stearyl/behenyl)
〇Plandol-S: Dimer dilinoleate (phytosteryl/isostearyl/cetyl/stearyl/behenyl)
〇Plandol-G: Dimer dilinoleyl dimer dilinoleate bis(behenyl/isostearyl/phytosteryl)
Plandool-DP: Bis-diglyceryl polyacyladipate-2
○Plandool-ISS: Phytosteryl isostearate ○Plandool-SUN: Phytosteryl sunflower seed oil fatty acid ○Plandool-MAS: Phytosteryl macadamia nut oil fatty acid ○Plandool-LG1: Phytosteryl lauroyl glutamate / octyldodecyl / behenyl
〇Plandol-LG2: Lauroyl glutamate di(phytosteryl/octyldodecyl)
〇Plandool-LG3: Lauroyl glutamate di(phytosteryl/octyldodecyl/behenyl)
〇Plandol-LG4: Lauroyl glutamate di(phytosteryl/octyldodecyl/behenyl)
〇LUSPLAN DD-IS: Dimer dilinoleyl diisostearate 〇LUSPLAN PI-DA: Di(isostearyl/phytosteryl) dimer dilinoleate
〇LUSPLAN DD-DHR: Dimer Dilinoleyl Hydrogenated Rosin Condensate 〇LUSPLAN SR-DM4: Dimer Dilinoleyl Dimer Dilinoleate, Caprylic/Capric Triglyceride 〇Neosolue-Aqualio: Cyclohexanedicarboxylic Acid Bisethoxydiglycol 〇Neosolue-Aqua: (Eicosanedioic Acid/Tetradecanedioic Acid) Polyglyceryl-10, Glycerin 〇Neosolue-AquaS: (Eicosanedioic Acid/ Tetradecanediolate (Polyglyceryl-10, Glycerin) ○Neosolue-DiSM: Diisostearyl Malate ○Neosolue-MCT: Caprylic/Capric Triglyceride ○Phytocompo-PP: Hydrogenated Lecithin, Phytosterol ○Phytocompo-C: Hydrogenated Lecithin, Phytosterol, Ceramide 2, Ceramide 3, Ceramide 6II
〇Phytocompo-SP: Hydrogenated lecithin, phytosterol, BG, glycerin 〇Phytopressome MEL: Glycolipid, hydrogenated lecithin, BG, purified water 〇Elcalactone MCT: γ-docosalactone, tri(caprylic/capric acid) glyceryl 〇Elcalactone DES: γ-docosalactone, diethyl sebacate 〇Tremoist-TP: Tremella fuciformis polysaccharide 〇Tremoist-SL: Tremella fuciformis polysaccharide aqueous solution (1%)
〇YOFCO MAC: Macadamia nut oil fatty acid cholesteryl 〇PrimeLipid-PI: Hydrogenated lecithin, phytosterol, lecithin, tocopherol 〇Inulin-SC: Inulin 〇RepairLipid-DSL: Sodium stearoyl lactylate, diethyl sebacate 〇STR-100W: Titanium dioxide, hydrated silica 〇FINEX-33W: Zinc oxide, hydrated silica 〇DIS-AB-10W: Titanium dioxide, hydrated silica, hydrogen dimethicone, water, BG, PEG-9 dimethicone

Claims (1)

A method for producing a compound represented by the following general formula (1), comprising the steps (1) to (3) below.
(1) A step of reacting lecithin containing phosphatidylcholine with phospholipase A2 in water or a mixture of water and an organic solvent. (2) A step of reacting the product obtained in step (1) with phospholipase D in water or a mixture of water and an organic solvent. (3) A step of hydrolyzing the product obtained in step (2) in water or a mixture of water and an organic solvent under acidic conditions.
(In the formula, R represents a saturated or unsaturated aliphatic acyl group having 14 to 24 carbon atoms.)