JP3274522B2 - Novel carboxybetaine, its production method and its use - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel carboxybetaine having excellent moisturizing properties, a method for producing the same, and a cosmetic or detergent composition containing the same.

[0002]

2. Description of the Related Art
Moisturizing agents are added to hair cosmetics such as shampoos and rinses and skin cosmetics to impart a moist feel to hair and skin. Usually, propylene glycol, glycerin, urea, sorbitol, alkylene oxide adducts of alcohols and the like have been used as humectants.

However, none of these compounds is necessarily satisfactory in terms of moisture retention, moisture absorption, moisture absorption rate, feel and the like. In addition, natural polysaccharide components such as hyaluronic acid have excellent moisturizing properties and feel, but are not easily available and are expensive, so that their use range has been limited to relatively high-grade cosmetics.

[0004] Therefore, the development of compounds which are excellent in moisturizing properties, easily obtainable and inexpensive, and which can be incorporated into cleaning compositions such as shampoos, body shampoos, kitchen detergents, hair cosmetics such as rinses and skin cosmetics, etc. Was desired.

[0005]

Under these circumstances, the present inventors have conducted intensive studies, and as a result, the carboxybetaine represented by the following general formula (1) has excellent moisturizing properties and various cleaning bases. The present invention was found to be useful as a cosmetic base and the like, and to be simple and inexpensive to produce.

That is, the present invention provides the following general formula (1)

[0007]

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[Wherein R ¹ is a group having 1 to 1 carbon atoms having a hydroxyl group.
An alkyl group of 6,

[0009]

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Wherein R ³ and R ⁴ are the same or different and each represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, and R ² represents a hydrogen atom or a hydroxyl group Which represents an alkyl group having 1 to 6 carbon atoms which may be substituted with a carboxybetaine), a method for producing the carboxybetaine, and a cosmetic and detergent composition containing the carboxybetaine.

In R ¹ in the general formula (1), which represents the carboxybetaine of the present invention, the alkyl group having 1 to 6 carbon atoms includes methyl, ethyl, propyl, isopropyl, butyl, t- Examples thereof include a butyl group, a pentyl group, and a hexyl group.Examples of the alkyl group having 1 to 6 carbon atoms substituted with a hydroxyl group include those obtained by substituting the above-mentioned alkyl group with a hydroxyl group, specifically, a hydroxymethyl group,
1-hydroxyethyl group, 1-hydroxypropyl group,
Examples thereof include a 2-hydroxyethyl group, a 1,2-hydroxypropyl group, a 1-hydroxybutyl group, a 1-hydroxypentyl group, and a 1-hydroxyhexyl group. Among the alkyl group having 1 to 6 carbon atoms which is substituted with the hydroxyl groups, especially a human Dorokishimechiru group, 1-hydroxyethyl group, 2-hydroxyethyl group is preferred.

When R ¹ is a group represented by —N (R ³ ) (R ⁴ ), R ³ and R ⁴ may be the same or different and each have 1 to 1 carbon atoms which may be substituted by a hydrogen atom or a hydroxyl group. Although an alkyl group having 6 is shown, examples of the alkyl group having 1 to 6 carbon atoms which may be substituted with the hydroxyl group include the same groups as those described above for R ¹ . Particularly preferred groups among R ³ and R ⁴ are a hydrogen atom, a methyl group and a 1-hydroxyethyl group.

Further, examples of the alkyl group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group in R ² include the same groups as those in R ¹ . Particularly preferred groups in R ² are a hydrogen atom and a methyl group.

The carboxybetaine (1) of the present invention can be prepared by, for example, reacting an amine compound represented by the general formula (2) with a haloacetic acid represented by the general formula (3) or a salt thereof according to the following reaction formula. Can be manufactured.

[0015]

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Wherein R ¹ and R ² have the same meaning as described above, X represents a halogen atom, and Y represents a hydrogen atom or a cation.

In the production method of the present invention, the amine compound (2), which is a raw material, comprises a carboxylic acid compound represented by the general formula (4) and a carboxylic acid compound represented by the general formula (5) according to the following reaction formula (A).
Or an urea or urea derivative represented by the general formula (6) and an N, N-dimethyl compound represented by the formula (7) according to the following reaction formula (B). It can be obtained by reacting with ethanolamine in an inert solvent.

[0018]

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[0019] wherein, R ^2, R ³ and R ⁴ are as defined above, R ⁵ is 1 to carbon atoms which is substituted by hydroxyl
6 alkyl groups or

[0020]

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In the above reaction formula (A), examples of the carboxylic acid compound (4) include acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, glycolic acid, lactic acid, glyceric acid, and pyrrolidone carboxylic acid. Examples of the amine compound (5) include N, N-dimethylethylenediamine, N, N-dimethyl-N'-methylethylenediamine, and the like.

In order to carry out the reaction represented by the reaction formula (A), the amine compound (5) is used in a molar amount of 0.5 to 3 times, especially 1.0 to 1.5 times the carboxylic acid compound (4). 40-200 ° C., especially 80-1
It is preferred to carry out the reaction at a temperature of 50 ° C.

Examples of the inert solvent used herein include solvents having low compatibility with water, such as toluene and xylene. From the viewpoint of improving the reaction efficiency, the reaction is preferably performed while trapping generated water.

In the above reaction formula (B), examples of the urea derivative (6) include methyl urea, ethyl urea,
2-hydroxyethyl urea and the like.

In order to carry out the reaction represented by the reaction formula (B), N, N-dimethylethanolamine (7)
Urea or a urea derivative (6) is used in an amount of 0.5 to 5 times, especially 1.0 to 2.0 times, in an inert solvent containing an acid.
It is preferred to carry out the reaction at a temperature of 0 to 150 ° C.

Examples of the acid used here include hydrochloric acid, acetic acid, sulfuric acid, and a mixed acid of two or more selected from them. Examples of the inert solvent include water, methanol, ethanol, isopropyl alcohol, dimethyl sulfoxide,
Examples thereof include polar solvents such as dimethylformamide and the like, and a mixed solvent of two or more kinds selected from these. Among them, water and a mixed solvent of water and a lower alcohol are particularly preferable.

In the production method of the present invention, in the general formula (3) representing haloacetic acid or a salt thereof as another raw material,
Examples of the halogen atom represented by X include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. In addition, examples of the cations among those represented by Y include sodium ions and potassium ions. Specific examples of such a haloacetic acid or a salt thereof include sodium chloroacetate, sodium bromoacetate, chloroacetic acid and the like.

The production method of the present invention is carried out by reacting the amine compound (2) obtained by the above reaction formula (A) or (B) with haloacetic acid or a salt thereof (3). Is 1 to 5 moles, particularly 1 to 2 moles, of haloacetic acid or a salt thereof (3) with respect to the amine compound (2), and is used in an inert solvent at 20 to 120C, particularly 40 to 90C.
It is preferred to carry out at a temperature of

Examples of the inert solvent used herein include polar solvents such as water, methanol, ethanol, isopropanol, dimethylformamide, and dimethyl sulfoxide, or a mixed solvent of two or more selected from these.
Of these, water and a mixed solvent of water and a lower alcohol are preferred.

It is preferable that the base is present in an amount of 1 to 3 moles with respect to the amine compound (2) during the reaction, since the reaction can proceed efficiently. Examples of the base used here include sodium hydroxide and potassium hydroxide.

The reaction product obtained as described above contains, in addition to the target product carboxybetaine (1), an inorganic salt as a by-product, unreacted amine compound (2), haloacetic acid or a salt thereof (3). And / or hydrolysates thereof. The proportion of each component in the reaction product depends on the type of raw materials used, their reaction ratio, the type and amount of solvent used, the reaction temperature, and the like. Therefore, depending on the purpose of use, it is possible to use the reaction product as it is, but when a higher purity product is required, for example, a solvent separation method,
It can be purified by a known purification method such as an ion exchange chromatography method and an electrodialysis method.

The carboxybetaine (1) thus obtained has excellent moisturizing properties, and is therefore used not only as a moisturizer but also as a cleanser for skin and hair, a body shampoo, a shampoo, a kitchen detergent and the like. It can also be applied.

To prepare the cosmetic of the present invention using carboxybetaine (1), 0.1 to 20% by weight, especially 0.5 to 10% by weight, of carboxybetaine (1) is blended in the cosmetic. Is preferred.

The cosmetic of the present invention includes, in addition to the carboxybetaine (1), components used in ordinary cosmetics, for example, ethylene glycol, diethylene glycol, triethylene glycol, higher polyethylene glycols, propylene glycol and dipropylene. Glycol,
More polypropylene glycols, 1,3-butylene glycol, butylene glycols such as 1,4-butylene glycol, glycerin, diglycerin, more polyglycerins, sorbitol, mannitol,
Sugar alcohols such as xylitol and maltitol, glycerin ethylene oxide (hereinafter abbreviated as EO), propylene oxide (hereinafter abbreviated as PO) adducts, sugar alcohols EO and PO adducts, galactose, glucose, fructose, etc. Monosaccharides and their EO and PO adducts,
Polysaccharides such as maltose and lactose and polyhydric alcohols such as EO and PO adducts; hydrocarbons such as liquid paraffin, squalane, petrolatum, and solid paraffin; natural oils such as olive oil, jojoba oil, evening primrose oil, coconut oil, and tallow , Isopropyl myristate, cetyl isooctanoate,
Oily components such as ester oils such as neopentyl glycol dicaprate, silicone oils such as methyl silicone and methyl phenyl silicone, higher fatty acids such as isostearic acid and oleic acid; POE alkyl ether, PO
E-branched alkyl ether, POE sorbitan ester,
POE glycerin fatty acid ester, POE hydrogenated castor oil, sorbitan ester, glycerin fatty acid ester,
Nonionic surfactants such as polyglycerin fatty acid esters, phosphoric acid type, sulfonic acid type, sulfuric acid type, anionic surfactants such as carboxylic acid type, and other amphoteric surfactants,
Cationic surfactants, etc .; vitamins, triclosan,
Fungicides such as trichlorocarban; anti-inflammatory agents such as dipotassium glycyrrhizinate and tocopherol acetate; anti-dandruff agents such as zinc pyrithione and octopirox; agents such as activators and ultraviolet absorbers; preservatives such as methylparaben and butylparaben; Amine oxides, foaming agents such as fatty acid alkanolamides, inorganic salts, viscosity modifiers such as polyethylene glycol stearate ethanol, pearling agents, fragrances, pigments, antioxidants; montmorillonite, saponite, heclite, veegum, kunibia, smecton, etc. Water-swellable clay minerals; polysaccharides such as carrageenan, xanthan gum, sodium alginate, pullulan, methylcellulose, carboxymethylcellulose, hydroxyethylcellulose and hydroxypropylcellulose;
Other polymers such as carboxyvinyl polymer and synthetic polymer such as polyvinylpyrrolidone; titanium oxide, kaolin,
An extender such as mica, sericite, zinc white, and talc, and a pigment such as a polymer powder such as polymethyl methacrylic acid and nylon powder can be appropriately compounded as long as the effects of the present invention are not impaired.

The cosmetic of the present invention can be produced by a usual method, and the dosage form can be any dosage form such as liquid, cream, solid, powder, etc. It is preferably in the form of a cream.

On the other hand, in order to obtain the detergent composition of the present invention using carboxybetaine (1), carboxybetaine (1) is incorporated in the composition in an amount of 0.5 to 50% by weight, particularly 1 to 30% by weight. Is preferred.

In the cleaning composition of the present invention, various surfactants usually used for cleaning agents can be arbitrarily used as long as the effects of the present invention are not impaired.

Specifically, examples of the anionic surfactant include sulfate and sulfonate.
Alkyl sulfate, polyoxyethylene alkyl sulfate,
Sulfosuccinic, taurate, isethionate,
Examples of the surfactant include α-olefin sulfonic acid-based surfactants, and examples of the carboxylate-based surfactant include fatty acid soaps, ether carboxylic acid-based surfactants, and acylated amino acid-based surfactants. Phosphate-based surfactants and the like can be mentioned.

Examples of the amphoteric surfactant include carbobetaine-based, phosphobetaine-based, sulfobetaine-based, and imidazolinium betaine-based amphoteric surfactants.

Examples of the nonionic surfactant include polyoxyalkylene addition type, polyoxypropylene / polyoxyethylene addition type, amine oxide type, mono or diethanolamide type, sorbitan fatty acid ester, glycerin fatty acid ester, and sucrose fatty acid. Examples include esters, alkyl saccharides, and polyhydric alcohols of N-polyhydroxyalkyl fatty acid amides.

Examples of the cationic surfactant include a mono- or di-alkyl-added quaternary ammonium salt having a linear or branched alkyl group and an alkylene oxide added to the alkyl group. A straight chain monoalkyl quaternary ammonium salt having 12 to 16 carbon atoms, a quaternary monoalkyl quaternary ammonium salt having 20 to 28 carbon atoms
Grade ammonium salts and the like are preferably used.

These surfactants may be used alone or in combination of two or more. The amount of the surfactant varies depending on the dosage form, but it is 2 to 60% by weight, especially 10 to 50% by weight in the detergent composition of the present invention. % By weight is preferred. The weight ratio to carboxybetaine (1) is preferably in the range of 1: 2 to 1:50, particularly 1: 3 to 1:30.

In addition to the above components, the detergent composition of the present invention contains components used in ordinary detergents, for example, ethylene glycol, diethylene glycol, triethylene glycol, and more polyethylene glycols, propylene glycol and dipropylene. Glycol, higher polypropylene glycols, butylene glycols such as 1,3-butylene glycol and 1,4-butylene glycol, glycerin, diglycerin, higher polyglycerins, sorbitol, mannitol, xylitol, maltitol and the like. Sugar alcohols, ethylene oxide (hereinafter abbreviated as EO) or propylene oxide (hereinafter abbreviated as PO) adducts of glycerin, EO or PO adducts of sugar alcohols, simple substances such as galactose, glucose, fructose, etc. And its EO or PO adducts, polysaccharides of maltose, lactose sugar and its EO or PO adducts; hydrocarbons such as liquid paraffin, squalane, petrolatum, solid paraffin, olive oil, jojoba oil, evening primrose oil , Coconut oil, natural oils such as tallow, isopropyl myristate, cetyl isooctanoate,
Oily components such as ester oils such as neopentyl glycol dicaprate, silicone oils such as dimethyl silicone and methyl phenyl silicone, higher fatty acids such as isostearic acid and oleic acid; bactericides such as vitamins and triclosan trichlorocarban; dipotassium glycyrrhizinate; Anti-inflammatory agents such as tocopherol acetate, anti-dandruff agents such as zinc pyrithione and octopirox, activators, agents such as ultraviolet absorbers; water-swellable clay minerals such as montmorillonite, saponite, hecrite, veegum, kunibia, smecton; carrageenan; Xanthan gum, sodium alginate, pullulan, methylcellulose, carboxymethylcellulose, hydroxyethylcellulose,
Polysaccharides such as hydroxypropyl cellulose, carboxyvinyl polymer, other polymers such as synthetic polymers such as polyvinylpyrrolidone; extender pigments such as titanium oxide, kaolin, mica, sericite, zinc white, talc, polymethylmethacrylic acid, Pigments such as polymer powders such as nylon powder; preservatives such as methyl paraben and butyl paraben; viscosity modifiers such as inorganic salts, polyethylene glycol stearate, and ethanol; pearlizing agents; fragrances; It can be appropriately compounded within a range that does not impair the effects of the invention.

The cleaning composition of the present invention can be produced by a usual method, and the dosage form can be any dosage form such as a liquid, a paste, a solid, and a powder. It is particularly preferable to use a liquid state or a paste state.

[0045]

EFFECT OF THE INVENTION Since the carboxybetaine of the present invention has excellent moisturizing properties, shampoos, body shampoos,
It is useful as a compounding component in detergent compositions such as kitchen detergents, hair cosmetics such as rinses, and various skin cosmetics. Also,
This compound can be easily and inexpensively produced using readily available raw materials, and is an extremely economically advantageous compound.

[0046]

EXAMPLES The present invention will be described in more detail with reference to the following Examples, which should not be construed as limiting the invention thereto.

Example 1 55.0 ml of N, N-dimethylethylenediamine was added to a reactor.
(0.5 mol) and 50.0 ml of concentrated hydrochloric acid under ice-cooling
(0.5 mol) was added dropwise to obtain a hydrochloride. Thereafter, an aqueous solution of 120.12 g (2 mol) of urea and hydrochloric acid-acetic acid (4 ml)
-4 ml) of an aqueous solution, and reacted under reflux for 4 hours. After completion of the reaction, 30% aqueous sodium hydroxide solution 20 was added to the reaction solution.
0 ml was added, the mixture was extracted with chloroform, the obtained chloroform layer was concentrated to dryness, and then redissolved in 200 ml of water. An aqueous solution of 58.2 g (0.5 mol) of sodium chloroacetate was added dropwise to the obtained aqueous solution at room temperature over 1 hour. After the completion of the dropwise addition, the temperature was gradually raised, and the reaction was carried out at 70 ° C. for 15 hours. After the reaction, ion exchange chromatography (ion exchange resin: BIO-RAD, A
G501-X8), and the solvent was distilled off under reduced pressure to obtain 72.8 g of N, N-dimethyl-N-ethylureidoglycine. This was prepared by HPLC (column: Shimadzu Seika Gel SCR101N, eluent: water,
Detector: RI), the purity was 99%. ¹ H-NMR (D ₂ O); δ (ppm) D ₂ O: 4.6
5: 3.68 (s, 2H, d), 3.55 (t, 2H,
b), 3.33 (m, 2H, a), 3.07 (s, 6
H, c).

[0048]

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Example 2 In a reactor, 76.05 g (1.0 mol) of glycolic acid, 500 ml of toluene, N, N-dimethylethylenediamine 1
32 ml (1.2 mol) was added and reacted under reflux for 20.5 hours. This reaction was performed while trapping generated water. After completion of the reaction, the mixture was concentrated to dryness, and 300 ml of water was added to redissolve it. To the resulting aqueous solution, an aqueous solution of 139.8 g (1.2 mol) of sodium chloroacetate was added dropwise at room temperature over 1.5 hours. After the completion of the dropwise addition, the temperature was gradually raised, and the reaction was carried out at 70 ° C. for 12 hours. After completion of the reaction, ion exchange chromatography (ion exchange resin: BIO-RAD)
The product was purified by AG501-X8) and the solvent was distilled off under reduced pressure to obtain 162 g of N, N-dimethyl-N-glycolamidoethylglycine. This is HPL
C (column: Shimadzu Gel SCR101, manufactured by Shimadzu Corporation)
N, eluent: water, detector: RI), the purity was 99.5%. ¹ H-NMR (D ₂ O); δ (ppm) D ₂ O: 4.7
1: 4.05 (s, 2H, a), 3.89 (s, 2H,
d), 3.55-3.78 (m, 4H, b), 3.18
(S, 6H, c).

[0050]

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Example 3 L-2-Pyrrolidone-5-carboxylic acid
12 g (1.0 mol), 500 ml of toluene and 110 ml (1.0 mol) of N, N-dimethylethylenediamine were added and reacted under reflux for 15.5 hours. This reaction was performed while trapping generated water. After completion of the reaction, the mixture was concentrated to dryness, and 400 ml of water was added to redissolve. In the obtained aqueous solution,
At room temperature, an aqueous solution of 128.1 g (1.1 mol) of sodium chloroacetate was added dropwise over 2 hours. After the completion of the dropwise addition, the temperature was gradually raised, and the reaction was carried out at 70 ° C. for 15 hours. After completion of the reaction, purification is performed by ion exchange chromatography (ion exchange resin: AG501-X8, manufactured by BIO-RAD), and the solvent is distilled off under reduced pressure to give N, N-dimethyl-N-2-pyrrolidone-. 156.8 g of 5-carboxamidoethylglycine was obtained. This is HPLC
(Column: Shimadzu Corporation, Shimadzu Gel SCR101N,
Eluent: water, detector: RI), purity 9
9%. ¹ H-NMR (D ₂ O); δ (ppm) D ₂ O: 4.5
5: 4.00 to 4.15 (m, 1H, b), 3.66
(S, 2H, e), 3.38 to 3.63 (m, 4H,
c), 3.05 (m, 6H, d), 1.74-2.39.
(M, 4H, a).

[0052]

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[0053]

Example 1 A hair treatment having the following composition was prepared. 2-dodecylhexadecyltrimethylammonium chloride 2 (% by weight) stearyltrimethylammonium chloride 2 Compound of Example 2 5 Stearyl alcohol 5 Lanolin 3 Liquid paraffin 3 Polypeptide (collagen hydrolyzate) 5 Hydroxyethyl cellulose (1% aqueous solution viscosity 8, 000cp) 0.5 Polyethylene (5) oleyl ether 0.5 Methyl paraben 0.2 Fragrance 0.4 Water balance This hair treatment is excellent in imparting softness to hair, and it gives a non-greasy and moist feel. Met.

[0054]

Example 5 A lotion having the following composition was prepared. Lactic acid 0.03 (% by weight) Sodium lactate 0.84 Compound of Example 3 5 Glycerin 2 Polyoxyethylene oleyl ether (20EO adduct) 1 Ethanol 10 Fragrance 0.3 Water Balance This lotion loses moisturizing properties due to sweat It was not sticky, and it was not sticky, giving a moist feeling.

[0055]

Example 6 A powder bath preparation having the following composition was prepared. Sodium bicarbonate 67 (% by weight) Dextrin 30 Compound 2 of Example 1 Fragrance 0.5 Dye 0.5 This powder bath had an excellent moisturizing effect on the skin and gave a moist feeling.

[0056]

Example 7 A paste-like facial cleanser having the following composition was prepared. Sodium sesquilauryl phosphate 25 (% by weight) dipotassium myristyl sulfosuccinate 5 cocoyl diethanolamide 2 polyethylene glycol monostearate 4 compound of Example 5 5 carboxyvinyl polymer 0.5 paraben 0.3 fragrance 0.3 purified water balance This face wash The material had a refreshing finish, a moist feel, and no crispness.

[0057]

Example 8 A liquid body shampoo having the following composition was prepared. Triethanolamine lauryl phosphate 20 (% by weight) Alkyl saccharide [C ₁₂ -O- (G) _2.5 ] ^{* 15} Sodium lauroyl sarcosine 5 Compound of Example 2 8 Xanthan gum 0.5 Propylene glycol 3 Perfume 0.7 Purified water Balance * 1: C ₁₂ represents a lauryl group, and G represents glucose. This body shampoo was moist without any bulk after washing.

[0058]

Example 9 An anti-dandruff shampoo having the following composition was prepared. Lauryl dimethylamine betaine acetate 10 (wt%) Sodium N-lauroylglutamate 10 Pyroctone auramine (Octopirox, Hoechst) 0.5 Ethylene glycol distearate 2 Compound of Example 2 5 Perfume 0.5 Water balance This anti-dandruff shampoo had no squeaky feeling when washing and rinsing hair, and the finish was moist without stickiness.

[0059]

Table 7 Example 10 A dishwashing detergent having the following composition was prepared. Polyoxyethylene (4) lauryl ether sodium sulfate 8 (wt%) polyoxyethylene (20) myristyl ether 5 lauryl dimethylamine oxide 3 ethanol 3 compound of Example 3 perfume 0.1 water balance There was little bulkiness of the hands after use and it was moist.

Continued on the front page (51) Int.Cl. ⁷ Identification code FI A61K 7/40 A61K 7/40 7/50 7/50 C07C 231/12 C07C 231/12 275/14 275/14 C07D 207/28 C07D 207 / 28 C11D 1/90 C11D 1/90 (72) Inventor Yoshiaki Fujikura 271-6 Yamamotocho, Utsunomiya City, Tochigi Prefecture (56) Reference International Publication 92/5240 (WO, A1) (58) Fields investigated (Int. Cl) . ^7, DB name) CA (STN) CAOLD (STN ) REGISTRY (STN)

Claims (5)

(57) [Claims] 1. The following general formula (1): Wherein, R ¹ represents an alkyl group having 1 to 6 carbon atoms having a hydroxyl group, ## STR2 ## Wherein R ³ and R ⁴ are the same or different and each represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, and R ² is substituted with a hydrogen atom or a hydroxyl group. Represents an alkyl group having 1 to 6 carbon atoms which may be
A carboxybetaine represented by 2. R ¹ is a methyl or ethyl group having a hydroxyl group, H ₂ N— or The carboxybetaine according to claim 1, which is: 3. The following general formula (2): Wherein, R ¹ represents an alkyl group having 1 to 6 carbon atoms having a hydroxyl group, embedded image Wherein R ³ and R ⁴ are the same or different and each represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may be substituted with a hydroxyl group, and R ² is substituted with a hydrogen atom or a hydroxyl group. Represents an alkyl group having 1 to 6 carbon atoms which may be
Amine compounds and the following general formula _{(3) X-CH 2 -COOY} (3) represented in [wherein, X represents a halogen atom, Y represents a hydrogen atom or a cation] haloacetic acid or represented by The method for producing carboxybetaine according to claim 1, wherein the method is reacted with a salt. 4. A cosmetic comprising the carboxybetaine according to claim 1 or 2. 5. A detergent composition comprising the carboxybetaine according to claim 1 or 2.