JPH10273426A - Agent for treating hair - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a hair-treating agent excellent in biodegradability and usability and further excellent in emulsion stability due to the increase in the viscosity of the product by including a specific quaternary ammonium amino acid salt. SOLUTION: This hair-treating agent contains a quaternary ammonium amino acid salt of formula I (X<1> is an amide group; R<1> is an alkyl, etc.; R<2> is an alkylene, etc.; R<3> , R<4> are each a 1-4C alkyl, etc.; R<5> is a 1-4C alkyl, etc.; Q<-> is the anion of an amino acid). The hair-treating agent containing the compound of formula I preferably further contains a tertiary amine amino acid neutralization product of formula II (R<8> is a 6-28C alkyl, etc.; R<9> and R<10> re each a 1-28C alkyl, etc.; QH is an amino acid). In the treating agent, the compound of formula I or the mixture of the compound of formula I with the compound of formula II is preferably contained in an amount of 0.1-30 wt.%.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a hair treatment agent.

[0002]

2. Description of the Related Art A quaternary ammonium salt having a long-chain alkyl group, which has a carboxylic acid, a sulfonic acid, or a phosphoric acid as a counter ion, has conventionally been used as a quaternary ammonium organic acid salt used in a hair treatment agent. (JP-A-8-208443) is known.

[0003]

However, these quaternary ammonium salts have problems in biodegradability, irritation to humans, and usability (feel after use represented by hair slip, moist feeling, etc.). Although it can be improved as compared with the conventional chloride salt, it is still not enough. In addition, there are problems that the product viscosity is not increased, the emulsion stability is poor, and the emulsification is difficult.

[0004]

Means for Solving the Problems As a result of intensive studies to solve these problems, the present inventors have found that hair containing an amino acid ammonium salt whose quaternary ammonium counterion is an amino acid anion as an essential component. The treating agent was found to be excellent in biodegradability and usability, and the product viscosity was increased and the emulsification stability was also excellent, and the present invention was completed.

The present invention provides a compound represented by the following general formula (1):
It is a hair treatment agent containing a quaternary ammonium amino acid salt (A) as an essential component.

[0006]

Embedded image

Where X¹Represents an amide group. R¹Is
Alkyl group, alkenyl group or hydroxyalkyl group
Represents, R^TwoIs an alkylene group, alkenylene group or hydride
Roxyalkylene group, and R¹And R^TwoCarbon number of
Is 6 to 32. R^ThreeAnd R^FourAre the same young
Is different and R¹-X¹-R^Two-Groups (wherein, R¹,
X ¹, R^TwoIs the same as described above), R⁶-X^Two-R⁷-Group
(Where X^TwoRepresents an ester group. R⁶Is an alkyl
Group, alkenyl group or hydroxyalkyl group,
⁷Is an alkylene group, alkenylene group or hydroxya
Represents a alkylene group, and R⁶And R⁷The total carbon number of
6 to 32), an alkyl group having 1 to 4 carbon atoms, or
Represents a hydroxyalkyl group having 1 to 4 carbon atoms. R^FiveIs
C1-C4 alkyl group or C1-C4 hydroxy
Represents a silalkyl group. Q^-Represents the amino acid anion
You. Hereinafter, the present invention will be described in detail.

[0008]

BEST MODE FOR CARRYING OUT THE INVENTION The hair treatment composition of the present invention contains a quaternary ammonium amino acid salt (A) as an essential component. The quaternary ammonium amino acid salt (A) in the hair treatment composition of the present invention is represented by the general formula (1).
In the general formula (1), X ¹ is an amide group.
The amide group can be represented by -CONH- or -NHCO-.

In the general formula (1), R ¹ is an alkyl group, an alkenyl group or a hydroxyalkyl group. These may be residues obtained by removing carboxyl groups from higher fatty acids or residues obtained by removing amino groups from primary amines. The higher fatty acid and the primary amine are not particularly limited as long as the conditions for the total number of carbon atoms of R ¹ and R ² described below are satisfied.
Usually, those having 6 to 28 carbon atoms, preferably 12 to 12 carbon atoms
24. When the number of carbon atoms is 5 or less, not only the texture of the hair is inferior, but also irritation to the skin may increase. When the number of carbon atoms is 29 or more, the emulsifiability may be inferior. Of these, those having 16 to 24 carbon atoms are more preferable because they can give the hair a moist feeling.

The higher fatty acids include, for example, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, undecylic acid, lauric acid, tridecylic acid, myristic acid, pentadecylic acid, palmitic acid, margaric acid, stearic acid, Examples include nonadecyl acid, behenic acid, oleic acid, linoleic acid, linolenic acid, and the like. Also,
Palm oil fatty acids, palm kernel oil fatty acids, tallow fatty acids, hardened tallow fatty acids, lanolin fatty acids, soybean fatty acids, and the like, which are mixtures thereof, can also be used.

The primary amine includes, for example, octylamine, decylamine, laurylalamine, myristylamine, cetylamine, stearylamine, behenylamine, oleylamine and the like.

In the above formula (1), R ² is an alkylene group, alkenylene group or hydroxyalkylene group. These are not particularly limited as long as the following conditions regarding the total number of carbon atoms of R ¹ are satisfied, but usually they have 1 to 4 carbon atoms. Examples of such a group include a methylene group, an ethylene group, a propylene group, a butylene group, a hydroxymethyl group, a hydroxyethyl group, a hydroxypropyl group, and a hydroxybutyl group. Among these, a methylene group, an ethylene group and a propylene group are preferred from the viewpoint of price.

In the above general formula (1), the total of the carbon number of R ^{1 and} the carbon number of ² is 6 to 32. If the total number of carbon atoms is less than 6, not only the texture of the hair is inferior, but also the irritancy to the skin may increase, and if it exceeds 32, the emulsifiability may deteriorate. Of these, hair can be given a moist feeling, so that the total carbon number is 16
~ 28 are preferred.

In the above general formula (1), R ³ and R ⁴
Are the same or different and are each an R ¹ -X ¹ -R ² -group,
⁶ -X ² -R ⁷ - group, an alkyl group having 1 to 4 carbon atoms, or a hydroxyalkyl group having 1 to 4 carbon atoms. Hereinafter, these will be described in detail.

In the above R ¹ -X ¹ -R ² -group,
R ¹ , X ¹ and R ² are the same as those described above. Among them, those having a total carbon number of 16 to 28 are preferable since they can give a moist feeling to hair. In the above R ⁶ —X ² —R ⁷ — group, X ² is an ester group. The ester group is -COO- or -O
It can be represented by CO-.

[0016] The R ⁶ -X ² -R ⁷ - In the group, R ⁶
Is an alkyl group, an alkenyl group or a hydroxyalkyl group. These may be residues obtained by removing carboxyl groups from higher fatty acids, or residues obtained by removing hydroxyl groups from higher alcohols. The higher fatty acid and the higher alcohol are not particularly limited as long as the conditions for the sum of the number of carbon atoms of R ^{6 and} the number of carbon atoms of R ⁷ described below are satisfied, but usually those having 6 to 28 carbon atoms are preferable. Has 12 to 24 carbon atoms. When the number of carbon atoms is 5 or less, not only the texture of the hair is inferior, but also irritation to the skin may increase. When the number of carbon atoms is 29 or more, the emulsifiability may be inferior. Of these, since the hair can be given a moist feeling, it has 16 to 16 carbon atoms.
24 are more preferred.

Examples of the higher fatty acids include those exemplified above. As the higher alcohol, for example, octyl alcohol, decyl alcohol,
Lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol, oleyl alcohol and the like.

In the above R ⁶ -X ² -R ⁷ -group, R ⁷
Is an alkylene group, alkenylene group or hydroxyalkylene group. These are not particularly limited as long as the following conditions regarding the total number of carbon atoms of R ⁶ are satisfied,
Usually, the carbon number is 1-4. Examples of these include, for example, those exemplified above.

[0019] The R ⁶ -X ² -R ⁷ - In the group, R ⁶
And the total number of carbon atoms of R ⁷ are from 6 to 32.
When the total number of carbon atoms is less than 6, not only the texture of the hair is inferior, but also the irritation to the skin may increase.
If it exceeds 2, the emulsifiability may be poor. Among them, those having a total carbon number of 16 to 28 are preferable since they can give a moist feeling to hair.

Examples of the alkyl group having 1 to 4 carbon atoms or the hydroxyalkyl group having 1 to 4 carbon atoms include a methylene group, an ethylene group, a propylene group, a butylene group, a hydroxymethyl group, a hydroxyethyl group, and a hydroxypropyl group. , A hydroxybutyl group and the like.

In the general formula (1), R ⁵ is an alkyl group having 1 to 4 carbon atoms or a hydroxyalkyl group having 1 to 4 carbon atoms. Examples of these include a methyl group, an ethyl group, a propyl group, a butyl group, a hydroxymethyl group, a hydroxyethyl group, a hydroxypropyl group, a hydroxybutyl group, and the like. Particularly, a methyl group, an ethyl group and a hydroxyethyl group are preferable from the viewpoint of cost.

The amino acid salt (A) of the quaternary ammonium is a counter ion represented by Q in the general formula (1).
^- quaternary ammonium represented by the general formula excluding (a)
If, Q ^- is composed of an anion of an amino acid represented by. Examples of the quaternary ammonium (a), a counter ion in the formula (1) above Q ^- as long as represented by the general formula excluding, if specific examples of this, for example, And combinations of R ^{1 to} R ⁵ and X ¹ shown in (1) to (16) in Tables 1 and 2 and the like.

[0023]

[Table 1]

[0024]

[Table 2]

The anion of the amino acid which is a counter ion of the quaternary ammonium amino acid salt (A) includes:
For example, glycine, alanine, valine, leucine, isoleucine, serine, threonine, cysteine, methionine, asparagine, glutamine, phenylalanine, tyrosine, proline, tryptophan, aspartic acid,
Examples include anions of amino acids such as glutamic acid, cysteinic acid, lysine, arginine, histidine and the like.

Of these, anions obtained from glycine, alanine, valine, leucine, isoleucine, aspartic acid, glutamic acid and cysteinic acid are preferred. In particular, aspartic acid and glutamic acid, which are acidic amino acids, are more preferable in terms of cost and ease of salt exchange reaction. These can be used alone or as a mixture of two or more.

The hair treatment composition of the present invention comprising the quaternary ammonium amino acid salt (A) as an essential component, further comprises:
It preferably contains a neutralized amino acid of a tertiary amine (B) represented by the following general formula (2).

[0028]

Embedded image

In the formula, R ⁸ is an alkyl group having 6 to 28 carbon atoms, an alkenyl group having 6 to 28 carbon atoms, a hydroxyalkyl group having 6 to 28 carbon atoms, an R ¹ -X ¹ -R ² -group, or ,
Represents an R ⁶ —X ² —R ⁷ — group. R ⁹ and R ¹⁰ are the same or different and are an alkyl group having 1 to 28 carbon atoms, an alkenyl group having 1 to 28 carbon atoms, a hydroxyalkyl group having 1 to 28 carbon atoms, an R ⁶ -X ² -R ⁷ -group Or R ¹ -X ¹
—R ² — represents a group. QH represents an amino acid.

In the above general formula (2) representing the amino acid neutralized product (B) of the tertiary amine, R ⁸ has 6 to 2 carbon atoms.
An alkyl group having 8 carbon atoms, an alkenyl group having 6 to 28 carbon atoms, a hydroxyalkyl group having 6 to 28 carbon atoms, and the above R ¹ -X ^1-
R ² - group or the R ⁶ -X ² -R ⁷ - is a group.

The C6-C28 alkyl group, C6-C28 alkenyl group or C6-C28 hydroxyalkyl group includes, for example, hexyl group,
Heptyl, octyl, nonyl, dodecyl, tetradecyl, hexadecyl, octadecyl, docosyl, tetradecyl, hexadecyl, octadecyl, docosyl, 2-ethylhexyl, 2-hexyldecyl, 2-octyl Undecyl, hexene, heptene, octene, nonene, decenyl, dodecenyl, tetradecenyl, hexadecenyl, octadecenyl, hydroxyoctadecyl and the like. When the number of carbon atoms is 5 or less, not only the texture of the hair is inferior, but also the irritation to the skin and the like increases, and the number of carbon atoms is 29.
With the above groups, the emulsifiability may be poor. Among these, a group having 12 to 24 carbon atoms is preferable, and furthermore, a moist feeling can be imparted to the hair.
Is more preferred.

In the above general formula (2), R ⁹ and R ¹⁰
Are the same or different, an alkyl group having 1 to 28 carbon atoms, an alkenyl group having 1 to 28 carbon atoms, a hydroxyalkyl group having 1 to 28 carbon atoms, the above R ⁶ -X ² -R ⁷ -group, or the above R ¹ -X ¹ -R ² - is a radical.

Examples of the alkyl group having 1 to 28 carbon atoms, the alkenyl group having 1 to 28 carbon atoms and the hydroxyalkyl group having 1 to 28 carbon atoms include those exemplified above. A group having 29 or more carbon atoms may have poor emulsifiability. Among these, a group having 1 to 24 carbon atoms is preferable, and further, because of good texture and emulsion stability at 50 ° C., an alkyl group having 1 to 4 carbon atoms or 1 to 24 carbon atoms is preferable.
4 hydroxyalkyl groups are more preferred.

Amino acid neutralized tertiary amine (B)
Is composed of a tertiary amine (b) represented by the general formula except for the amino acid QH in the general formula (2), and an amino acid represented by QH. The tertiary amine (b) may be any of those represented by the general formula (2) except for the amino acid QH, and specific examples thereof include, for example, Tables 3 to 5 Ni (a) ~
The combination of R ^{8 to} R ¹⁰ shown in (W) is exemplified.

[0035]

[Table 3]

[0036]

[Table 4]

[0037]

[Table 5]

As the amino acids constituting the amino acid neutralized product (B) of the tertiary amine, the amino acids exemplified as the anion of the amino acid in the amino acid salt (A) of the quaternary ammonium can be suitably used.

The quaternary ammonium amino acid salt (A) is usually prepared by preparing a tertiary amine having an R ¹ -X ¹ -R ² -group and then converting the tertiary amine to an alkyl halide such as methyl chloride. And quaternized with an alkylating agent such as dialkyl sulfate such as dimethyl sulfate or dialkyl carbonate such as dimethyl carbonate, and then salt-exchanged with an amino acid or a salt thereof. In particular, from the viewpoint that no inorganic salt is generated and that the emulsion stability is good, it is preferable that the quaternary compound be produced by quaternizing with a dialkyl carbonate such as dimethyl carbonate and then performing salt exchange with an amino acid.

The tertiary amine having an R ¹ —X ¹ —R ² — group is usually obtained by an amidation reaction in which an alkylaminoalkyleneamine such as dimethylaminopropylamine and a carboxylic acid such as behenic acid are dehydrated and condensed. Can be manufactured. In the above amidation reaction, the amount of the alkylaminoalkyleneamine used is, based on the carboxylic acid,
Usually, it is 0.1 to 5.0 moles, preferably 0.3 mole.
~ 3.0-fold molar. The reaction temperature of the amidation reaction is usually 100 to 220 ° C, preferably 120 to 18 ° C.
0 ° C. The reaction is very slow below 100 ° C.
Above 0 ° C., coloring becomes severe.

When dialkyl carbonate is used as the alkylating agent in the above quaternization reaction, the amount used is usually 0.5 to 5.0 moles, preferably 0.1 mole, per mole of the tertiary amine. It is 7 to 2.0 times mol. The reaction temperature of the quaternization reaction is usually 50 to 150 ° C, preferably 80 to 150 ° C.
120 ° C. If the temperature is lower than 50 ° C., not only the reaction is very slow, but also the product may be solidified and cannot be stirred, and if the temperature is higher than 150 ° C., the coloring becomes intense.

In the above salt exchange reaction with the amino acid, the amount of the amino acid used is usually 0.5 to 3.0 times mol, preferably 0.5 mol, to the produced quaternary ammonium salt.
２．０2.0 times mol. The reaction temperature of the salt exchange reaction with the amino acid is usually 50 to 150 ° C, preferably 70 to 150 ° C.
120 ° C. If the temperature is lower than 50 ° C., the solidification may not be possible, and if the temperature is higher than 150 ° C., the coloring becomes intense.

Amino acid neutralized product of the above tertiary amine (B)
Can be produced by neutralizing a tertiary amine with an amino acid. In the neutralization reaction, the amount of the amino acid to be used is generally 0.5 to 3.0 times, preferably 0.5 to 2.0 times, the mole of the tertiary amine. The reaction temperature of the above-mentioned neutralization reaction is usually 50 to 150 ° C, preferably 70 to 120 ° C. If the temperature is lower than 50 ° C., the solidification may not be possible, and if the temperature is higher than 150 ° C., the coloring becomes intense.

The quaternary ammonium amino acid salt (A) may be used alone or after use as represented by biodegradability, hypoallergenicity to humans, and usability (such as hair slippage and moist feeling). Fully demonstrates the performance of hair texture).
However, when the (A) and the amino acid neutralized tertiary amine (B) are used in combination, the product viscosity of the hair treatment agent can be further increased, and the emulsion stability can be further improved. In this case, the weight ratio of (A) / (B) is usually 99.9 / 0.1 to 50/50, preferably 99.50.
9 / 0.1 to 70/30. If the proportion of (A) is less than 50% by weight, the texture of the hair after use, which is typified by slippery and moist feeling, may be poor.

The amount of the quaternary ammonium amino acid salt (A) or the mixture of the above (A) and the above tertiary amine amino acid neutralized product (B) in the hair treatment composition of the present invention. However, usually 0.1 to hair treatment agent
30% by weight. Preferably, it is 0.5 to 20% by weight. If the amount is less than 0.1% by weight, the texture of the hair after use, which is typified by the slippery and moist feeling of the hair, may be deteriorated. If the amount exceeds 30% by weight, the hair tends to gel.

The application of the hair treatment composition of the present invention is generally applicable to all the use of conventionally used hair treatment compositions containing a quaternary ammonium salt, but in particular, rinses, conditioners, treatments, etc. , Shampoo, hair dye, mousse, etc.

When the hair treatment composition of the present invention is used as a rinse, a conditioner or a treatment, it is usually used as the quaternary ammonium amino acid salt (A) and, if desired, the tertiary amine amino acid neutralized product (B). ) Other than nonionic surfactants, oils, humectants, chelating agents, lower alcohols, high molecular compounds, fragrances, coloring agents,
Contains preservatives, UV absorbers, water, etc.

Examples of the nonionic surfactant include 1: 1 type coconut oil fatty acid diethanolamide, lauryl dimethylamine oxide, glyceryl monostearate, ethylene glycol monostearate, polyethylene glycol monostearate, polyethylene distearate. Glycol, sorbitan monolaurate, polyoxyethylene sorbitan monolaurate, polyoxyethylene dioleic acid methyl glucoside, polyoxyethylene tallow alkyl hydroxy myristyl ether, ethylene glycol distearate, and the like. In particular, glyceryl monostearate or ethylene glycol monostearate is preferred because of good emulsion stability at 50 ° C.

Examples of the oil component include higher alcohols such as cetyl alcohol, stearyl alcohol and behenyl alcohol; fatty acid esters such as octyl myristate, cetyl 2-ethylhexanoate, isopropyl myristate and cetyl palmitate; solid paraffin;
Examples include hydrocarbon compounds such as liquid paraffin and squalane; and silicones such as dimethylpolysiloxane, modified silicone in which various organic groups are introduced into some of the methyl groups of dimethylpolysiloxane, and cyclic dimethylpolysiloxane. In particular, higher alcohols or silicones are preferred because they can give the hair a moist feeling.

The humectants include, for example, glycerin, diglycerin, sodium pyrrolidonecarboxylate and the like. In particular, glycerin is preferred in terms of price. Examples of the chelating agent include sodium ethylenediaminetetraacetate and 1-hydroxyethane-1,1.
-Sodium diphosphonate and the like. They are,
It can be blended as needed.

The lower alcohols include, for example,
Examples include ethanol, propylene glycol, dipropylene glycol and the like. These can be blended as needed.

Examples of the high molecular compound include cationized cellulose, cationized guar gum, polyethylene glycol, polypropylene glycol, sodium polyacrylate, hydroxyethyl cellulose, protein derivatives, N-methacryloyloxyethyl-N, N-
And dimethylammonium-α-N-methylcarboxybetaine / methacrylic acid alkyl ester copolymer. In particular, cationized cellulose or cationized guar gum is preferred because it can give the hair a moist feeling.

When used as a rinse, conditioner or treatment, the amount of the quaternary ammonium amino acid salt (A) or the above (A) and the tertiary amine is usually used in the hair treatment composition of the present invention. The mixture with the neutralized amino acid (B) is 0.5 to 20% by weight, the nonionic surfactant is 0 to 5% by weight, and the oil content is 0.5%.
-30% by weight, the humectant is 0-10% by weight, the chelating agent, the lower alcohols, the high molecular compound, etc. are 0-10% by weight, and the water is 25-99% by weight. The oil content is determined from the aspect of the texture of the hair after use represented by the slippery and moist feeling of the hair, from the above (A) or the above (A)
It is preferable that the weight ratio of the mixture of the tertiary amine amino acid neutralized product (B) and the oil component be 1/1 to 1/4.

In addition, anionic surfactants, amphoteric surfactants, cationic surfactants and the like may be used in combination as long as the effects of the present invention are not impaired.

Examples of the anionic surfactant include sodium lauryl sulfate, sodium polyoxyethylene lauryl sulfate, triethanolamine polyoxyethylene lauryl sulfate, sodium polyoxyethylene lauryl ether acetate, polyoxyethylene coconut fatty acid monoethanolamide. Sodium sulfate, disodium polyoxyethylene lauryl sulfosuccinate, disodium polyoxyethylene lauroylethanolamide sulfosuccinate, sodium coconut fatty acid methyltaurine, magnesium coconut fatty acid methyltaurine, coconut fatty acid sarcosine sodium, coconut fatty acid sarcosine triethanolamine , N-coconut fatty acid acyl-L-
Sodium glutamate, N-coconut fatty acid acyl-L
-Triethanolamine glutamate, sodium lauroylmethyl-β-alanine, N-lauroyl-N-methyl-β-alaninetriethanolamine, sodium lauryl phosphate and the like.

Examples of the amphoteric surfactant include coconut oil fatty acid amidopropyldimethylaminoacetic acid betaine, lauryldimethylaminoacetic acid betaine, 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, and laurylhydroxysulfonate. Betaine, sodium lauroylamidoethylhydroxyethylcarboxymethylbetainehydroxypropylphosphate, sodium β-laurylaminopropionate, and the like.

As the cationic surfactant, quaternary ammonium salts other than (A) used in the present invention can be used. For example, stearyltrimethylammonium chloride, behenyltrimethylammonium chloride, distearyldimethylammonium chloride , Lanolin ethyl sulfate fatty acid aminopropylethyldimethylammonium,
Lactate of diethylaminoethylamide stearate, lactate of dimethylaminopropylamide stearate and the like can be mentioned.

When the hair treatment composition of the present invention is used as a shampoo, it is usually used in addition to the quaternary ammonium amino acid salt (A) and, if desired, the tertiary amine amino acid neutralized product (B). , An anionic surfactant, an amphoteric surfactant, a nonionic surfactant, a humectant, a chelating agent, a polymer compound, a fragrance, a coloring agent, a preservative, an ultraviolet absorber, water and the like. As such anionic surfactants, amphoteric surfactants, nonionic surfactants, humectants, chelating agents, and high molecular compounds, those described above can be suitably used.

When used as a shampoo, the amount of the quaternary ammonium amino acid salt (A) or the neutralized amino acid (A) and tertiary amine (B) ) Is 0.5 to 10% by weight, the anionic surfactant is 1.0 to 30% by weight,
0 to 10% by weight of the amphoteric surfactant, 0.5 to 10% by weight of the nonionic surfactant, and 0 to 1% of the humectant
0% by weight, the chelating agent, the polymer compound, etc.
5% by weight and 25-98% by weight of water.

In addition, a cationic surfactant may be used together as long as the effects of the present invention are not impaired. As the cationic surfactant, the above-mentioned cationic surfactant and the like can be suitably used. Further, other additives may be contained as needed. For example, a higher fatty acid such as stearic acid can be blended as an oil component in addition to the above-described oil component, and trichlorocarbanilide, sulfur, salicylic acid, zinc pyrithione, isopropylmethylphenol, and the like can be blended as a drug.

When used as a hair dye, the hair treatment composition of the present invention generally comprises the above-mentioned quaternary ammonium amino acid salt (A) and, if desired, the above-mentioned tertiary amine amino acid neutralized product (B). In addition, it contains an acid dye, a solvent, a pH adjuster, a thickener, water and the like.

The acidic dye is not particularly limited, but may be any one belonging to an azo dye or an anthraquinone dye. Examples of the solvent include lower alcohols such as benzyl alcohol and isopropyl alcohol;
-Methylpyrrolidone and the like. Examples of the pH adjuster include citric acid. Examples of the thickener include carboxymethyl cellulose, xanthan gum and the like.

When used as a hair dye, the amount of the quaternary ammonium salt (A) or the amino acid neutralized product of the above (A) and the tertiary amine is used in the hair treatment composition of the present invention. 0.1 to 5% by weight of a mixture with (B),
0.5 to 10% by weight of the acid dye and 1 to 3 of the solvent
0% by weight, the pH adjuster is 0 to 5% by weight, the thickener is 0 to 5% by weight, and the water is 45 to 98.4% by weight.

In addition, anionic surfactants, amphoteric surfactants, nonionic surfactants, and cationic surfactants may be used in combination as long as the effects of the present invention are not impaired. As the anionic surfactant, amphoteric surfactant, nonionic surfactant and cationic surfactant, those described above can be suitably used. Further, other additives may be contained as needed. For example,
An oil, a humectant, a chelating agent or a polymer compound as described above, a fragrance, a coloring agent, a preservative, an ultraviolet absorber, water and the like can be blended.

When the hair treatment composition of the present invention is used as a hair setting agent such as mousse, the quaternary ammonium amino acid salt (A) and, if desired, the amino acid neutralized tertiary amine are used. In addition to (B), it contains a polymer compound, an oil, a humectant, a chelating agent, a lower alcohol, a nonionic surfactant, a fragrance, a coloring agent, a preservative, an ultraviolet absorber, water and the like.

In particular, when the above composition is used as a hair foam or a hair spray, it is filled in a can with liquefied petroleum gas, dimethyl ether and the like. By doing this,
The advantage is that the can is not rusted.

Examples of the polymer compound include, in addition to those exemplified above, acrylic resin alkanolamine, carboxyvinyl polymer, polyvinylpyrrolidone / vinyl acetate copolymer, and the like. Examples of the oil component include waxes such as refined mokuro and beeswax in addition to the above-described oil components. As the humectant, chelating agent, lower alcohols and nonionic surfactant, those described above and the like can be suitably used.

When used as a hair setting agent such as mousse, the compounding amount of the hair treatment composition of the present invention is the above
Amino acid salt of secondary ammonium (A) or the above (A)
0.1 to 10% by weight of a mixture of the above and a tertiary amine amino acid neutralized product (B);
0% by weight, 0.5 to 10% by weight of the oil, 0 to 5% by weight of the humectant, 0 to 5% by weight of the chelating agent, 0.5 to 30% by weight of the lower alcohol, non-ionic 0 to 5% by weight of water-soluble surfactant, 15 to 98.4% by weight of water
It is.

In addition, anionic surfactants, amphoteric surfactants and cationic surfactants as described above may be used in combination as long as the effects of the present invention are not impaired.

The pH of the hair treatment composition of the present invention is usually from 3 to
9 If the number is less than 3 or more than 9, counter ion exchange occurs, so that irritation to the skin increases, the texture of the hair after use represented by slippery and moist feeling of the hair deteriorates, The performance as the quaternary ammonium salt of the invention may not be sufficiently exhibited.

[0071]

EXAMPLES The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples.

Production Example 1 Behenic acid 34 was placed in a stirred reactor equipped with a thermometer.
0 g and 153 g of dimethylaminopropylamine were charged and subjected to a dehydration condensation reaction at a reaction temperature of 140 to 150 ° C., and unreacted dimethylaminopropylamine was distilled off. Thereafter, 424 g of the obtained dehydrated condensate, 99 g of dimethyl carbonate, and 170 g of isopropyl alcohol were charged into a stirring autoclave, and the reaction temperature was set to 110 to 13.
The mixture was stirred and reacted at 0 ° C. for 12 hours. Next, 147 g of glutamic acid was added, and salt exchange was performed while decarbonating at a reaction temperature of 60 to 80 ° C. Thereafter, 1755 g of water was charged, and the temperature was 60 to 90 ° C. and the degree of decompression was 100 mm under a nitrogen stream.
Isopropyl alcohol and unreacted dimethyl carbonate were removed with Hg. The pH was adjusted to 5 with citric acid to obtain a glutamate salt of compound (a) in (3) of Table 1.

Production Example 2 Behenic acid 34 was placed in a stirred reactor equipped with a thermometer.
0 g and 153 g of dimethylaminopropylamine were charged and subjected to a dehydration condensation reaction at a reaction temperature of 140 to 150 ° C., and unreacted dimethylaminopropylamine was distilled off. Then, 424 g of the obtained dehydrated condensate and 308 g of isopropyl alcohol were placed in a stirring autoclave.
Was charged, and 53 g of methyl chloride was blown in over 3 hours while maintaining the reaction temperature at 80 to 90 ° C. with stirring, followed by aging for 3 hours. After distilling off unreacted methyl chloride, 169 g of sodium glutamate and 17 parts of water
55 g, and under a nitrogen stream, a processing temperature of 80 to 90 ° C.
Isopropyl alcohol was removed while performing salt exchange at a reduced pressure of 100 mmHg. The pH was adjusted to 5 with citric acid to obtain a glutamate salt of compound (a) in (3) of Table 1.

Production Example 3 Behenic acid 34 was placed in a stirred reactor equipped with a thermometer.
0 g and 153 g of dimethylaminopropylamine were charged and subjected to a dehydration condensation reaction at a reaction temperature of 140 to 150 ° C., and unreacted dimethylaminopropylamine was distilled off. Thereafter, 424 g of the obtained dehydrated condensate, 99 g of dimethyl carbonate, and 170 g of isopropyl alcohol were charged into a stirring autoclave, and the reaction temperature was set to 110 to 13.
The mixture was stirred and reacted at 0 ° C. for 12 hours. Next, 133 g of aspartic acid was added, and salt exchange was performed while decarbonating at a reaction temperature of 60 to 80 ° C. Thereafter, 1755 g of water was charged, and the temperature was 60 to 90 ° C. and the degree of decompression was 100 mm under a nitrogen stream.
Isopropyl alcohol and unreacted dimethyl carbonate were removed with Hg. The pH was adjusted to 5 with citric acid to obtain aspartate of compound (a) in Table 3 (3).

Production Example 4 Behenic acid 28 was placed in a stirred reactor equipped with a thermometer.
9 g, 43 g of stearic acid and 153 g of dimethylaminopropylamine were charged, and the reaction temperature was 140 to 150.
The unreacted dimethylaminopropylamine was distilled off at ℃. Then, 424 g of the obtained dehydrated condensate, dimethyl carbonate 99 were placed in a stirred autoclave.
g, and 170 g of isopropyl alcohol,
The mixture was reacted at a reaction temperature of 110 to 130 ° C. with stirring for 12 hours. Next, 147 g of glutamic acid was added, and the reaction temperature was 6
Salt exchange was performed while decarboxylation at 0 to 80 ° C. afterwards,
1755 g of water was charged, and the temperature was 60 to 90 under a nitrogen stream.
Isopropyl alcohol and unreacted dimethyl carbonate were removed at 100 ° C. and a reduced pressure of 100 mmHg. The pH was adjusted to 5 with citric acid to obtain a glutamate salt of the compound (a) in Table 11 (11).

Production Example 5 In a stirred reactor equipped with a thermometer, stearic acid 2 was added.
84 g and 153 g of dimethylaminopropylamine
, And subjected to a dehydration condensation reaction at a reaction temperature of 140 to 150 ° C. to distill off unreacted dimethylaminopropylamine. Thereafter, 368 g of the obtained dehydrated condensate, 99 g of dimethyl carbonate, and 170 g of isopropyl alcohol were charged into a stirring autoclave, and the reaction temperature was set to 110 to 13.
The mixture was stirred and reacted at 0 ° C. for 12 hours. Next, 147 g of glutamic acid was added, and salt exchange was performed while decarbonating at a reaction temperature of 60 to 80 ° C. Thereafter, 1587 g of water was charged, and the temperature was reduced to 60 to 90 ° C. and the degree of decompression was set to 100 mm under a nitrogen stream.
Isopropyl alcohol and unreacted dimethyl carbonate were removed with Hg. The pH was adjusted to 5 with citric acid to obtain a glutamate salt of the compound (a) in Table 1 (2).

Production Example 6 279 g of hardened tallow fatty acid and 153 g of dimethylaminopropylamine were placed in a stirred reactor equipped with a thermometer.
g, and the mixture was subjected to a dehydration condensation reaction at a reaction temperature of 140 to 150 ° C., and unreacted dimethylaminopropylamine was distilled off. Thereafter, 368 g of the obtained dehydrated condensate, 99 g of dimethyl carbonate, and 170 g of isopropyl alcohol were charged into a stirring autoclave, and the reaction temperature was set to 110 to 13.
The mixture was stirred and reacted at 0 ° C. for 12 hours. Next, 147 g of glutamic acid was added, and salt exchange was performed while decarbonating at a reaction temperature of 60 to 80 ° C. Thereafter, 1587 g of water was charged, and the temperature was reduced to 60 to 90 ° C. and the degree of pressure reduction was set to 100 mm under a nitrogen stream.
Isopropyl alcohol and unreacted dimethyl carbonate were removed with Hg. The pH was adjusted to 5 with citric acid to obtain a glutamate salt of the compound (a) in Table 1 (2).

Production Example 7 Behenic acid 34 was placed in a stirred reactor equipped with a thermometer.
0 g, 134 g of dimethylaminoethanol, and an appropriate amount of p-toluenesulfonic acid as a catalyst were charged, and a dehydration condensation reaction was performed at a reaction temperature of 140 to 150 ° C., and unreacted dimethylaminoethanol was distilled off. Next, glutamic acid 1
47 g and water (1,674 g) were added thereto, and the mixture was neutralized under a nitrogen stream at a treatment temperature of 80 to 90 ° C., and the pH was adjusted to 5 with citric acid. A neutralized product was obtained.

Production Example 8 Behenic acid 34 was placed in a stirred reactor equipped with a thermometer.
0 g, 134 g of dimethylaminoethanol, and an appropriate amount of p-toluenesulfonic acid as a catalyst were charged, and a dehydration condensation reaction was performed at a reaction temperature of 140 to 150 ° C., and unreacted dimethylaminoethanol was distilled off. Next, 133 g of aspartic acid and 1,674 g of water were added, and under a nitrogen stream,
After neutralization at a treatment temperature of 80 to 90 ° C., p
By adjusting H to 5, a neutralized aspartic acid of the compound (b) of (g) in Table 4 was obtained.

Production Example 9 Behenic acid 28 was placed in a stirred reactor equipped with a thermometer.
9 g, 43 g of stearic acid, 134 g of dimethylaminoethanol, and an appropriate amount of p-toluenesulfonic acid as a catalyst were charged and subjected to a dehydration condensation reaction at a reaction temperature of 140 to 150 ° C., and unreacted dimethylaminoethanol was distilled off.
Next, 147 g of glutamic acid and 1674 g of water were charged, and neutralization was performed at a treatment temperature of 80 to 90 ° C. under a nitrogen stream, and then the pH was adjusted to 5 with citric acid. A glutamic acid neutralized compound (b) was obtained.

Production Example 10 Behenic acid 34 was placed in a stirred reactor equipped with a thermometer.
0 g and 153 g of dimethylaminopropylamine were charged and subjected to a dehydration condensation reaction at a reaction temperature of 140 to 150 ° C., and unreacted dimethylaminopropylamine was distilled off. Next, 147 g of glutamic acid and 1713 g of water
And neutralized at a treatment temperature of 80 to 90 ° C. under a nitrogen stream, and then adjusted to pH 5 with citric acid to obtain a glutamic acid neutralized product of the compound (b) in Table 4 (c). Obtained.

Production Example 11 Behenic acid 34 was placed in a stirred reactor equipped with a thermometer.
0 g and 153 g of dimethylaminopropylamine were charged and subjected to a dehydration condensation reaction at a reaction temperature of 140 to 150 ° C., and unreacted dimethylaminopropylamine was distilled off. Next, 147 g of aspartic acid and 1713 of water
g, and the mixture was neutralized at a treatment temperature of 80 to 90 ° C. under a nitrogen stream, and then adjusted to pH 5 with citric acid to neutralize the aspartic acid of compound (b) in Table 4 (c). I got something.

Production Example 12 Behenic acid 28 was placed in a stirred reactor equipped with a thermometer.
9 g, 43 g of stearic acid and 153 g of dimethylaminopropylamine were charged, and the reaction temperature was 140 to 150.
The unreacted dimethylaminopropylamine was distilled off at ℃. Next, 147 g of glutamic acid and 1713 g of water were charged, and the mixture was treated at a processing temperature of 80 under a nitrogen stream.
After neutralization at ~ 90 ° C, the pH was adjusted to 5 with citric acid to obtain a glutamic acid-neutralized compound (b) of Table 5 (U).

Production Example 13 In a stirred reactor equipped with a thermometer, stearic acid 2 was added.
84 g, 134 g of dimethylaminoethanol and an appropriate amount of p-toluenesulfonic acid as a catalyst were charged, and a dehydration condensation reaction was performed at a reaction temperature of 140 to 150 ° C., and unreacted dimethylaminoethanol was distilled off. Next, 147 g of glutamic acid and 1506 g of water were added, and neutralization was performed at a treatment temperature of 80 to 90 ° C. under a nitrogen stream, and the pH was adjusted to 5 with citric acid.
To obtain a glutamic acid-neutralized product of the compound (b) in Table 4 (T).

Production Example 14 In a stirred reactor equipped with a thermometer, 279 g of hardened tallow fatty acid, 134 g of dimethylaminoethanol, and
An appropriate amount of p-toluenesulfonic acid was charged as a catalyst, and a dehydration condensation reaction was performed at a reaction temperature of 140 to 150 ° C., and unreacted dimethylaminoethanol was distilled off. Next, 147 g of glutamic acid and 1,674 g of water were added, and neutralization was performed at a treatment temperature of 80 to 90 ° C. under a nitrogen stream, and then the pH was adjusted to 5 with citric acid. A glutamic acid neutralized compound (b) was obtained.

Production Example 15 In a stirred reactor equipped with a thermometer, stearic acid 2 was added.
84 g and 153 g of dimethylaminopropylamine
, And subjected to a dehydration condensation reaction at a reaction temperature of 140 to 150 ° C. to distill off unreacted dimethylaminopropylamine. Next, 147 g of glutamic acid and 1545 g of water
And neutralized at a treatment temperature of 80 to 90 ° C. under a nitrogen stream, and then adjusted to pH 5 with citric acid to obtain a glutamic acid-neutralized product of the compound (b) in Table 4 (no). Obtained.

Production Example 16 In a stirred reactor equipped with a thermometer, 279 g of hardened tallow fatty acid and 153 of dimethylaminopropylamine were added.
g, and the mixture was subjected to a dehydration condensation reaction at a reaction temperature of 140 to 150 ° C., and unreacted dimethylaminopropylamine was distilled off. Next, 147 g of glutamic acid and 1545 g of water
And neutralized at a treatment temperature of 80 to 90 ° C. under a nitrogen stream, and then adjusted to pH 5 with citric acid to obtain a glutamic acid neutralized product of the compound (b) in Table 5 (wa). Obtained.

Production Example 17 Behenic acid 34 was placed in a stirred reactor equipped with a thermometer.
0 g and 153 g of dimethylaminopropylamine were charged and subjected to a dehydration condensation reaction at a reaction temperature of 140 to 150 ° C., and unreacted dimethylaminopropylamine was distilled off. Then, 424 g of the obtained dehydrated condensate, 72 g of dimethyl carbonate, and 170 g of isopropyl alcohol were charged into a stirring autoclave, and the reaction temperature was set to 110 to 11.
The mixture was kept at 5 ° C and stirred for 12 hours to react. Next, 147 g of glutamic acid was added, and salt exchange was performed while decarbonating at a reaction temperature of 60 to 80 ° C. Thereafter, 1741 g of water was charged, and the temperature was 60 to 90 ° C. and the degree of decompression was 100 m under a nitrogen stream.
Isopropyl alcohol and unreacted dimethyl carbonate were removed at mHg. The pH was adjusted to 5 with citric acid.
A glutamate of the compound (a) of (3) and a neutralized glutamic acid of the compound (b) of (c) in Table 4 were obtained.

Production Example 18 In a stirred reactor equipped with a thermometer, 325 g of behenylamine and 94.5 g of monochloroacetic acid were charged.
A dehydration condensation reaction was performed at a reaction temperature of 90 to 100 ° C. Thereafter, the obtained dehydrated condensate 40 was placed in a stirred autoclave.
1.5 g and 308 g of isopropyl alcohol were charged, and while stirring, 70 g of trimethylamine was charged over 3 hours while maintaining the reaction temperature at 80 to 90 ° C., followed by aging for 3 hours. After distilling off unreacted trimethylamine,
169 g of sodium glutamate and 1755 g of water
Was added, and isopropyl alcohol was removed under a nitrogen stream while performing a salt exchange at a treatment temperature of 80 to 90 ° C. and a reduced pressure of 100 mmHg. The pH was adjusted to 5 with citric acid to obtain the glutamate salt of the compound (a) in (8) of Table 1.

Examples 1 to 10 and Comparative Examples 1 to 4 Using the compounds shown in Tables 1 to 5 prepared by the methods shown in Production Examples 1 to 18, the compositions (parts by weight) shown in Tables 6 to 8 were used. ), An appropriate amount of a fragrance and a dye are added, the pH is adjusted to 5 with citric acid, and water (remainder) is added to make the total amount 100 parts. Hair treatment agents were prepared and tested for skin irritation, hand, biodegradability, thickening, and emulsion stability. The results are shown in Tables 6 to 8.

[0091]

[Table 6]

[0092]

[Table 7]

[0093]

[Table 8]

The amino acid salt of quaternary ammonium (A) or the neutralized amino acid of tertiary amine (B) in Tables 6 to 8 is the quaternary ammonium (a) or Table 4 in Tables 1 and 2. The tertiary amine (b) of 3 to 5 is shown in combination with an amino acid. In addition, the composition ratios in the table are shown in terms of pure components of active ingredients.

The additives used in Examples 1 to 10 and Comparative Examples 1 to 4 shown in Tables 6 to 8 are as follows. Higher alcohol E1: Cetyl alcohol E2: Stearyl alcohol E3: Behenyl alcohol Fatty acid ester F1: Octyl myristate F2: Cetyl 2-ethylhexanoate Emulsifier: Glycerin monostearate Moisturizer: Glycerin Low silicone: Low polymerization degree dimethylpoly Siloxane High silicone: High degree of polymerization dimethylpolysiloxane

Polymer compound G1: Cationized cellulose G2: Cationized guar gum Hydrocarbon compound H1: Solid paraffin H2: Liquid paraffin chelating agent: EDTA-2Na Lower alcohol J1: Propylene glycol J2: Dipropylene glycol amino acid As: Aspartic acid Gl : Glutamic acid

The quaternary ammonium salts C1 to C3 used in Comparative Examples 1 to 3 are the following compounds. C1: Stearyltrimethylammonium chloride C2: Distearyldimethylammonium chloride C3: Stearate of behenyltrimethylammonium

Test Method <Skin irritation> 1.0% aqueous surfactant solutions of the compositions shown in Tables 6 to 8 were prepared, and were subjected to a closed
A patch test (after 48 hours, inside the upper arm) was performed and evaluated according to the following criteria. The result was shown by the total value. -Evaluation criteria- 0; No reaction (erythema) 1; Very mild erythema 2; Clear erythema 3; Medium to strong erythema 4;

<Hands> 4 g of each of the compositions shown in Tables 6 to 8 was taken, and water was added to make 200 cc. A hair bundle (length 15 cm, weight 5 g) washed with shampoo was immersed at 40 ° C. for 5 seconds. Then, the substrate was rinsed twice with warm water (200 ° C., 40 ° C.) for 30 seconds, and then dried overnight at 25 ° C. × 65% RH. The texture was scored on the following criteria using ten panelists for the flexibility, moist feeling, and smoothness of the hair bundle after rinsing and drying all day and night, and the total score was evaluated. -Scoring criteria- 0: Inferior to standard rinse 1; Slightly inferior to standard rinse 2: Equivalent to standard rinse 3: Slightly superior to standard rinse 4; Superior to standard rinse Note that Comparative Example 1 was used as the standard rinse.

<Biodegradability> 4 of the compositions shown in Tables 6 to 8
A 0 ppm surfactant aqueous solution was prepared and subjected to a biodegradability test in accordance with the 301A Die-Away test method of the OECD Chemicals Test Guideline, and evaluated according to the following criteria. -Evaluation Criteria- ◎: Very good biodegradability than standard surfactant ○: Good biodegradability than standard surfactant △: Equivalent to standard surfactant × ×: Biodegradable from standard surfactant Degradability is poor. Comparative Example 3 was used as a standard surfactant.

<Thickening> Thickening of the compositions shown in Tables 6 to 8 was checked. ○: viscosity sufficiently satisfactory as a rinse △; viscosity almost satisfactory as a rinse ×; viscosity not satisfactory as a rinse

<Emulsification Stability> The compositions shown in Tables 6 to 8 were checked for emulsification stability at 50 ° C. for 30 days. ；: Not separated △: partially separated ×: completely separated

From Tables 6 to 8, it can be seen that the quaternary ammonium amino acid salt (A) of the present invention or a mixture thereof with a tertiary amine amino acid neutralized product (B) has an irritation to the skin and the like. It is clear that the hair texture and the biodegradability are excellent, and the hair is extremely excellent. Furthermore, it is excellent in thickening and emulsion stability.

[0104]

Industrial Applicability The quaternary ammonium amino acid salt of the present invention has a good texture of hair after use represented by slippery and moist feeling of hair, good biodegradability, and low skin irritation. Therefore, it is useful as an environment- and human-friendly hair treatment agent. It is also excellent in thickening and emulsion stability, and is extremely useful as a hair treatment agent.

Claims (4)

[Claims] 1. A hair treatment agent comprising, as an essential component, a quaternary ammonium amino acid salt (A) represented by the following general formula (1). [In the formula, X ¹ represents an amide group. R ¹ represents an alkyl group, an alkenyl group or a hydroxyalkyl group;
² represents an alkylene group, alkenylene group or hydroxyalkylene group, and the total number of carbon atoms of R ¹ and R ² is 6 to 32. R ³ and R ⁴ may be the same or different and are each an R ¹ -X ¹ -R ² -group (wherein R ¹ , X ¹ , R
² is the same as defined above), an R ⁶ -X ² -R ⁷ -group (wherein X is
² represents an ester group. R ⁶ represents an alkyl group, an alkenyl group or a hydroxyalkyl group, R ⁷ represents an alkylene group, an alkenylene group or a hydroxyalkylene group, and the total number of carbon atoms of R ⁶ and R ⁷ is ⁶ to 32. ), An alkyl group having 1 to 4 carbon atoms, or 1 to 4 carbon atoms
4 represents a hydroxyalkyl group. R ⁵ has 1 to 1 carbon atoms
4 represents an alkyl group or a hydroxyalkyl group having 1 to 4 carbon atoms. Q ^- represents an anion of the amino acid. ] 2. In the general formula (1), R ³ and R
The hair treating agent according to claim 1, wherein ⁴ is the same or different and is an alkyl group having 1 to 4 carbon atoms or a hydroxyalkyl group having 1 to 4 carbon atoms. 3. Further, 3 represented by the following general formula (2)
The hair treatment composition according to claim 1 or 2, further comprising a neutralized amino acid (B) of a secondary amine. [Wherein, R ⁸ represents an alkyl group having 6 to 28 carbon atoms, an alkenyl group having 6 to 28 carbon atoms, a hydroxyalkyl group having 6 to 28 carbon atoms, an R ¹ -X ¹ -R ² -group (wherein, X ¹ represents an amide group, R ¹ represents an alkyl group, an alkenyl group or a hydroxyalkyl group, R ² represents an alkylene group,
Represents an alkenylene group or a hydroxyalkylene group, and the total number of carbon atoms of R ¹ and R ² is 6 to 32), or an R ⁶ -X ² -R ⁷ -group (where X ² is an ester R ⁶ represents an alkyl group, an alkenyl group or a hydroxyalkyl group, R ⁷ represents an alkylene group, an alkenylene group or a hydroxyalkylene group;
The total number of carbon atoms of ⁶ and R ⁷ is ⁶ to 32). R
⁹ and R ¹⁰ are the same or different and each have 1 to 28 carbon atoms.
Alkyl group, an alkenyl group of 1 to 28 carbon atoms, a hydroxyalkyl group having 1 to 28 carbon atoms, R ⁶ -X ² -R ⁷ -
Wherein R ⁶ , X ² and R ⁷ are the same as defined above, or
It represents an R ¹ -X ¹ -R ² -group (wherein R ¹ , X ¹ and R ² are the same as described above). QH represents an amino acid. ] 4. The hair treatment composition according to claim 1, wherein the amino acid is aspartic acid or glutamic acid.