JP7630811B2 - Allergen-reducing composition - Google Patents

Description

The present invention relates to an allergen-reducing composition.

Allergens such as dust mites, including Dermatophagoides farinae and Dermatophagoides pteronyssinus, and pollens, including cedar pollen and cypress pollen, have been known in recent years to cause allergic diseases, including asthma and atopic dermatitis. These allergens are present in textile products, including clothing, curtains, and bedding covers. As a result, allergen-reducing compositions that inactivate allergens are being developed.

Ellagic acid is said to be effective as a skin-whitening agent and anti-cancer agent (Patent Documents 1 and 2), but it was not known to have an allergen-reducing effect.

JP 2003-81826 A JP 2007-145836 A

The objective of the present invention is to provide an allergen-reducing composition that exhibits excellent allergen-reducing effects.

The present invention was completed based on the discovery that ellagic acid, which has been known to have a whitening effect, also has an allergen reducing effect.
(1) An allergen-reducing composition comprising one or more compounds selected from ellagic acid and hexahydroxydiphenate,
(2) A processed product obtained by processing the allergen-reducing composition containing the above-mentioned ellagic acid or hexahydroxydiphenate.

The present invention provides an allergen-reducing composition that has excellent allergen-reducing effects.

The ellagic acid used in the allergen-reducing composition of the present invention is known as a type of natural polyphenol compound contained in plants such as pomegranate fruit, and is obtained by extracting plants such as pomegranate fruit.

Ellagic acid can also be obtained by synthesizing hexahydroxydiphenate through an oxidative coupling reaction between a gallic acid ester such as methyl gallate, ethyl gallate, or propyl gallate and an oxidizing agent, and then reacting this hexahydroxydiphenate with an acid.

The hexahydroxydiphenate used in the allergen-reducing composition of the present invention can be obtained as described above, or by dispersing ellagic acid in water and making the pH of the resulting dispersion alkaline with sodium hydroxide or the like, thereby hydrolyzing two ester moieties within the ellagic acid molecule.

The allergen-reducing composition of the present invention can be used as is, for example, one or more compounds selected from ellagic acid or hexahydroxydiphenate, or can be used in the form of a liquid or powder.

When the allergen-reducing composition of the present invention is used as a liquid, it can be dispersed or dissolved in water, glycol-based compounds, petroleum-based compounds, alcohol-based compounds, glycol ether-based compounds, ketone-based compounds, amine-based compounds, etc.

Examples of glycol compounds include ethylene glycol, propylene glycol, butylene glycol, diethylene glycol, triethylene glycol, polyethylene glycols having a molecular weight of 1000 or less, and polypropylene glycols having a molecular weight of 1000 or less.
Examples of the petroleum-based compounds include linear or branched hydrocarbons having 6 to 12 carbon atoms and hydrocarbons having 6 to 16 carbon atoms and having an aromatic ring, examples of the alcohol-based compounds include ethanol, propyl alcohol, isopropyl alcohol, and butanol, examples of the glycol ether-based compounds include diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, and diethylene glycol monopropyl ether, examples of the ketone-based compounds include methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone, and examples of the amine-based compounds include ethanolamine, triethanolamine, propanolamine, N-methylpyrrolidone, and N-ethylpyrrolidone. These compounds may be used alone or in combination of two or more.

When used as a liquid agent, one or more surfactants selected from nonionic surfactants, anionic surfactants, cationic surfactants, and amphoteric surfactants can be further blended. Nonionic surfactants or anionic surfactants are preferred. Examples of nonionic surfactants include polyoxyethylene alkyl phenyl ethers, polyoxyethylene styryl phenyl ethers, polyoxyethylene alkyl ethers, polyoxyethylene alkenyl ethers, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters. Examples of anionic surfactants include alkyl benzene sulfonates, polyoxyethylene alkyl phenyl ether sulfates, and dialkyl sulfosuccinates. Examples of cationic surfactants include aliphatic amine salts and their quaternary ammonium salts. Examples of amphoteric surfactants include betaine-type surfactants and amino carboxylates.

When the allergen-reducing composition of the present invention is used as a powder, it is mixed with clay, calcium carbonate, talc, silica, etc.

The liquid or powder may be used together with acaricides, fungicides, antibacterial agents, chelating agents, rust inhibitors, fragrances, scale inhibitors, defoamers, antistatic agents, thickeners, fabric softeners, fabric softeners, deodorants, disinfectants, insecticides, and adhesives.

Acaricides include pyrethroid compounds such as natural pyrethrins, fenothrin, and permethrin, organophosphorus compounds such as fenitrothion, malathion, fenthion, and diazinon, dicofol, chlorbenzilate, hexythiazox, tebufenpyrad, pyridaben, amidoflumet, benzyl alcohol, benzyl benzoate, phenyl salicylate, cinnamaldehyde, hyssop oil, and carrot seed oil.

Examples of antifungal or antibacterial agents include 5-chloro-N-methylisothiazolone, methylene bisthiocyanate, 2-bromo-2-nitropropane-1,3-diol, glutaraldehyde, iodopropynyl butylcarbamate, zinc salt of pyridinethiol-N-oxide, 1,2-benzisothiazolone, 1,2-dibromo-2,4-dicyanobutane, chlorhexidine gluconate, 2-isopropyl-5-methylphenol, 3-methyl-4-isopropylphenol, orthophenylphenol, methyl parahydroxybenzoate, ethyl parahydroxybenzoate, and propyl parahydroxybenzoate. , butyl paraoxybenzoate, parachlorometaxylenol, parachlorometacresol, polylysine, benzalkonium chloride, didecyldimethylammonium chloride, N-n-butylbenzisothiazolone, N-octylisothiazolone, 2-(4-thiazolyl)benzimidazole, 2-methylbenzimidazolylcarbamate, tetrachloroisophthalonitrile, diiodomethylparatolylsulfone, parachlorophenyl-3-iodopropargylformal, 2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine, fatty acid glycerin esters, hinokitiol, etc.

The allergen-reducing composition of the present invention is used by being processed into coating agents such as paints, plastics, wallpaper, fibers, wood, concrete, metals, stone, glass, rubber, and the like.
In addition to the above, a liquid containing the allergen-reducing composition of the present invention may be used by spraying it into space, or by spraying or applying it to furniture such as chairs and sofas.

Examples of coating agents include water-based paints, oil-based paints, car wax, silicone-based coating agents, and fluorine-based coating agents. Examples of plastics include polyethylene, polypropylene, vinyl chloride, and ABS resin. Examples of wallpaper include polyvinyl chloride resin-based, polyolefin and other plastic-based, paper-based, fiber-based, and inorganic-based wallpaper.

The allergen-reducing composition of the present invention exerts an excellent allergen-reducing effect particularly in cleaning wet wipes, masks, filter materials, vacuum cleaner dust bags, clothing, interior items such as carpets, sofas, wallpaper and curtains, bedding such as futon covers, futon batting, sheets, pillowcases and mats, automobile parts such as car seats, car mats, ceiling materials and floor materials, stuffed toys, etc., which are based on such fibers.

Allergens that are reduced by the allergen-reducing composition of the present invention include allergens derived from mites in house dust, allergens derived from the hair and epithelium of pets such as dogs and cats, cockroaches, feathers, and mold, as well as pollen from cedar, mugwort, Japanese laurel, cypress, ragweed, and other plants, and natural rubber latex.

The allergen-reducing composition of the present invention will be described in more detail with reference to examples, but is not limited to these.

(Synthesis of Ellagic Acid)
1. 4 g of methyl gallate (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.) and 4 g of sodium hydrogen carbonate (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.) were dissolved in 120 g of ion-exchanged water, and the solution was placed in a 200 mL measuring cylinder. Air was then bubbled into the solution at a flow rate of 1 L/min using an air pump for 6 hours to obtain a precipitate.
2. The precipitate was filtered off, suspended in a 10% aqueous sulfuric acid solution, and stirred for 40 minutes. The suspension was filtered off, washed with ion-exchanged water, and air-dried at 25° C. to synthesize ellagic acid.

[Preparation of allergen-reduced composition]
Example 1
0.1 g of ellagic acid was added to 9.9 g of ion-exchanged water and the mixture was shaken to obtain a 1% dispersion of ellagic acid, thereby preparing the allergen-reduced composition of the present invention.

Example 2
An allergen-reduced composition of the present invention was prepared by dissolving 0.1 g of ellagic acid in a mixture of 8 g of diethylene glycol monomethyl ether and 1.9 g of ion-exchanged water to give a 1% solution of ellagic acid.

Example 3
The allergen-reducing composition of the present invention was prepared by dispersing 0.1 g of ellagic acid in 9.5 g of ion-exchanged water, adding 0.4 g of a 10% aqueous sodium hydroxide solution to dissolve the ellagic acid and obtaining a 1% solution of sodium hexahydroxydiphenate.

Example 4
The allergen-reducing composition of the present invention was prepared by dispersing 0.1 g of ellagic acid in 9.6 g of ion-exchanged water, and then adding 0.3 g of methyldiethanolamine (AMIETOL M12, manufactured by Eastman Chemical Co.) to dissolve the ellagic acid and obtain a 1% solution of the methyldiethanolamine salt of hexahydroxydiphenic acid.

Example 5
The allergen-reducing composition of the present invention was prepared by dissolving 0.1 g of pomegranate ellagic acid (ellagic acid purity 90%, manufactured by Sabinsa Japan Corporation) in 8 g of N-methylpyrrolidone and 1.9 g of ion-exchanged water to prepare a 0.9% solution of ellagic acid.

[Test Example 1]
Measurement of the reduction rate of cedar pollen allergens 1. Cry j1 monoclonal antibody 013 (Bio Dynamics Institute Co., Ltd.) diluted to 2 μg/mL with PBS (Fujifilm Wako Pure Chemical Industries, Ltd.) was added to an F16 MAXISORP NUNC-IMMUNO MODULE plate (NUNC Corporation) at 100 μL per well and allowed to stand at 4° C. for 1 day.
2. After standing, the liquid was discarded, and 200 μL of a blocking reagent {PBS containing 1% by weight bovine serum albumin (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.)} was added per well, and the plate was left to stand at 37° C. for 60 minutes.
3. The liquid in the wells was discarded, and the plate was rinsed with PBS (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.).
4. 50 μL of a solution obtained by diluting the allergen-reduced composition of the present invention 10-fold with ion-exchanged water was mixed with 1 mL of an allergen solution containing 12.5 ng/mL cedar pollen allergen Cry j1 (a solution prepared with PBS-T (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) to give a concentration of 12.5 μg/mL) (hereinafter referred to as standard cedar pollen allergen solution). As a control, the standard cedar pollen allergen solution was mixed with 50 μL of ion-exchanged water.
5. 100 μL of these mixtures were dropped into each well and allowed to stand at 37° C. for 60 minutes.
6. The liquid in the wells was discarded, and the plate was rinsed with PBS (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.).
7. Peroxidase-labeled Cry j1 monoclonal antibody 053 (Bio Dynamics Institute Co., Ltd.) was dissolved in distilled water at 200 μg/mL, and the solution was diluted 1200-fold with PBS-T (Fujifilm Wako Pure Chemical Industries, Ltd.) containing 1% by weight of bovine serum albumin. 100 μL of the solution was added per well and allowed to stand at 37° C. for 60 minutes.
8. The liquid in the wells was discarded, and the plate was rinsed with PBS (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.).
9. 6.5 mL of 0.2 mol/L phosphate buffer (pH 6.2) was mixed with ortho-phenylenediamine dihydrochloride (13 mg tablet, Fujifilm Wako Pure Chemical Industries, Ltd.) and 6.5 μL of 30% hydrogen peroxide solution, and 100 μL of the mixture was added per well and allowed to stand at 37° C. for 5 minutes.
50 μL of 10.2 mol/L aqueous sulfuric acid solution was added to each well, and the absorbance (OD 490 nm) was measured using a microplate spectrophotometer (manufactured by Tecan Japan Co., Ltd.).
11. The Cry j1 concentration was determined from the absorbance, and the cedar pollen allergen reduction rate was calculated using formula (2).

Cedar pollen allergen reduction rate (%) = (12.5 - (Cry j1 amount)) / 12.5 x 100 (2)

Table 1 shows the Cry j1 concentration and the reduction rate of cedar pollen allergens.

Table 1

[Test Example 2]
Measurement of mite allergen reduction rate 1. Anti-Der f2 monoclonal antibody 15E11 (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) diluted to 2 μg/mL with PBS (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was added at 100 μL per well to an F16 MAXISORP NUNC-IMMUNO MODULE plate (manufactured by NUNC Corporation), and the plate was allowed to stand at 4° C. for 3 days.
2. After standing, the liquid was discarded, and 200 μL of a blocking reagent {PBS containing 1% by weight bovine serum albumin (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.)} was added per well, and the plate was left to stand at 37° C. for 60 minutes.
3. The liquid in the wells was discarded, and the plate was rinsed with PBS (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.).
4. 1 mL of an allergen solution containing the mite allergen Der f2 (a solution prepared with PBS-T (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) so that the protein amount converted to Der f2 was 900 ng/mL) was mixed with 25 μL of each of the allergen-reduced compositions of the present invention in Examples 3 to 5. As a control, 25 μL of ion-exchanged water was mixed in place of the allergen-reduced compositions of the present invention in Examples 3 to 5.
5. 100 μL of the mixture was dropped into each well and allowed to stand at 37° C. for 60 minutes.
6. The liquid in the wells was discarded, and the plate was rinsed with PBS (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.).
7. Peroxidase-labeled anti-Der f2 monoclonal antibody 13A4 (manufactured by Fuji Film Wako Shibayagi Co., Ltd.) was dissolved in PBS-T (manufactured by Fuji Film Wako Pure Chemical Industries, Ltd.) containing 1% by weight of bovine serum albumin at 200 μg/mL, and then diluted 1200-fold with PBS-T (manufactured by Fuji Film Wako Pure Chemical Industries, Ltd.) containing 1% by weight of bovine serum albumin.
8. 100 μL of the 1200-fold diluted solution was added to each well, and the plate was left to stand at 37° C. for 60 minutes.
9. The liquid in the wells was discarded, and the plate was rinsed with PBS (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.).
10. One tablet of ortho-phenylenediamine dihydrochloride (13 mg Tablet, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) and 6.5 μL of 30% hydrogen peroxide were added to 6.5 mL of 0.2 mol/L phosphate buffer (pH 6.2), and the resulting solution was added in an amount of 100 μL per well and allowed to stand at 37° C. for 3 minutes.
50 μL of 11.2 mol/L aqueous sulfuric acid solution was added per well, and the absorbance (OD490 nm) was measured using a microplate spectrophotometer (manufactured by Tecan Japan Co., Ltd.) The protein concentration converted to Der f2 was determined from the absorbance, and the mite allergen reduction rate was calculated according to formula (1).

Mite allergen reduction rate (%) = (900 - (protein amount converted to Der f2)) / 900 x 100 (1)

Table 2 shows the Der f2 equivalent protein concentration and allergen reduction rate.

Table 2

(Preparation of Filters Treated with Allergen-Reduced Composition)
A 13 cm x 13 cm polypropylene nonwoven fabric (basis weight: 80 g/ ^m2 ) was immersed in 50 mL of a diluted solution prepared by diluting the allergen-reducing composition of Example 4 10 times with ion-exchanged water, and wrung to a wringing rate of 100% (wringing rate = (weight of fiber after immersion - weight of fiber before immersion) / weight of fiber before immersion x 100), and then heated and dried in a dryer at 105°C for 15 minutes to produce an allergen-reducing composition-processed filter.

[Test Example 3] (Test on cedar pollen allergen reduction using a filter treated with an allergen-reducing composition)
The allergen-reducing composition processed filter cut to 5cm x 5cm was placed in a zippered plastic bag, and 1mL of standard cedar pollen allergen liquid was added. After 1 hour, the cedar pollen allergen liquid was squeezed out of the zippered plastic bag, and the squeezed cedar pollen allergen liquid was centrifuged, and the supernatant was used as cedar pollen allergen extract. The cedar pollen allergen extract was subjected to a cedar pollen allergen reduction test according to the procedure for measuring the cedar pollen allergen reduction rate described in [Test Example 1]. The results are shown in Table 3.

[Table 3]

The allergen-reducing composition of the present invention can reduce allergens such as mites and pollen. The allergen-reducing composition of the present invention can also be used as an allergen-reducing composition for imparting an allergen-reducing function to coating agents such as paints, plastics, wallpaper, fibers, etc.

Claims (2)

An allergen -reducing composition comprising one or more compounds selected from ellagic acid or hexahydroxydiphenate, wherein the target allergen is at least one of cedar pollen and dust mites. A processed product produced by processing the allergen-reducing composition according to claim 1.