JPH09255638A - New quaternary ammonium salt, its production and hair cosmetic containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new quaternary ammonium salt useful as a new surfactant used as a base of softening agents for fabric, hair, etc. SOLUTION: This quaternary ammonium salt is represented by formula I [R<1> to R<3> are each a 1-6C straight-chain or branched alkyl or hydroxyalkyl; R<4> is H or same as R<1> to R<3> ; R<5> and R<6> are each H or an 8-22C straight or branched alkanoyl, alkenoyl or hydroxyalkanoyl; at least either one of R<5> and R<6> is an 8-22C straight-chain or branched alkanoyl, alkenoyl, or hydroxyalkanoyl; X is an anion], e.g. 2-dimethylamino-1,3-di(octadecanoyloxy) propane of formula II. The compound of formula I is obtained by reacting an aminoalcohol of formula III with a compound of the formula, R<7> Y (R<7> is R<5> or R<6> except H; Y is OH, an alkoxy or a halogen) to afford aminoester of formula IV and reacting the aminoester of formula IV with a quaternarizing agent of the formula, R<3> X.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel quaternary ammonium salt, a method for producing the same, and a hair cosmetic containing the same. More specifically, the present invention relates to a novel quaternary ammonium salt which is a novel surfactant and is used as a base of a softening agent for fabrics, hair and the like, a method for producing the same, and a hair cosmetic composition containing the same. .

[0002]

2. Description of the Related Art In recent years,
Surfactants used for fabrics and softeners for hair are
In addition to surface-active ability, it is required to have various properties such as safety, low irritation to skin, and biodegradability. Currently, as surfactants used in softeners,
Well-known are di long-chain alkyl dimethyl ammonium salts represented by the following formula (A), di long-chain alkyl imidazolines represented by the following formula (B), and the like.

[0003]

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(In the formula, R represents a long-chain alkyl group.)

[0005]

[Chemical 6]

(In the formula, R has the same meaning as described above, R'represents a long chain alkyl group, and E represents -O-, -NH- or -S-.) These surfactants are used. The softeners that have been used have been widely used because they are generally excellent in softness and fluffiness with respect to cloth and hair. However, while these surfactants are generally excellent in safety and performance as a base of a softening agent,
There was a problem with biodegradability, and after use, it did not decompose easily in rivers and the sea, and there was a problem that it existed for a long time.

Therefore, an object of the present invention is to provide a compound which is excellent in the softening effect on fibers and hair and is more biodegradable, and which is suitable as a softening agent base and a hair treatment base.

[0008]

In view of the above situation, the present inventors have made earnest studies to obtain a compound which is excellent as a softener for fabrics and hair, has high safety, and has good biodegradability. As a result, they found that the novel quaternary ammonium salt represented by the following general formula (1) meets the object of the present invention, and completed the present invention. That is, the present invention provides a quaternary ammonium salt represented by the general formula (1), a method for producing the same, and a hair cosmetic composition containing the same.

[0009]

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[Wherein R ¹ , R ² and R ³ are the same or different and are linear or branched alkyl or hydroxyalkyl groups having 1 to 6 carbon atoms, R ⁴ is H, and straight chain having 1 to 6 carbon atoms. Chain or branched alkyl group or hydroxyalkyl group, R ⁵ and
R ⁶ are the same or different and represent H, a straight-chain or branched alkanoyl group, an alkenoyl group or a hydroxyalkanoyl group having 8 to 22 carbon atoms, and at least one of R ⁵ and R ⁶ is a straight chain having 8 to 22 carbon atoms or It is a branched alkanoyl group, alkenoyl group or hydroxyalkanoyl group. X represents an anionic group. The present invention also provides an amino ester represented by the following general formula (4), which is useful as an intermediate for producing a quaternary ammonium salt represented by the general formula (1).

[0011]

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[In the formula, R ¹ , R ² , R ⁴ , R ⁵ and R ⁶ have the same meanings as described above. ]

[0013]

Embodiments of the present invention will be described below in detail. There is no report on the quaternary ammonium salt represented by the general formula (1) in the conventional publications, and the quaternary ammonium salt of the present invention is a novel compound.

In the quaternary ammonium salt represented by the general formula (1) of the present invention, R ¹ , R ² and R ³ are the same or different and are linear or branched alkyl groups having 1 to 6 carbon atoms or A hydroxyalkyl group is shown, specifically, a methyl group,
Examples include groups such as ethyl group, propyl group, butyl group, pentyl group, hexyl group, hydroxyethyl group, hydroxypropyl group, hydroxybutyl group and hydroxyhexyl group, and preferably methyl group, ethyl group or hydroxyethyl group. , And more preferably a methyl group.

R ⁴ represents H, a linear or branched alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group, and specifically, H, a methyl group, an ethyl group, a propyl group,
Examples thereof include a butyl group, a pentyl group, a hexyl group, a hydroxyethyl group, a hydroxypropyl group, a hydroxybutyl group, and a hydroxyhexyl group, preferably H, a methyl group, an ethyl group or a hydroxyethyl group, and more preferably H, a methyl group or an ethyl group.

R ⁵ and R ⁶ are the same or different and are H and have 8 carbon atoms.
~ 22 linear or branched alkanoyl group, alkenoyl group or hydroxyalkanoyl group, wherein at least one of R ⁵ and R ⁶ is a linear or branched alkanoyl group, alkenoyl group or hydroxyalkanoyl group having 8 to 22 carbon atoms. However, it is preferable that both R ⁵ and R ⁶ are linear or branched alkanoyl groups, alkenoyl groups or hydroxyalkanoyl groups having 8 to 22 carbon atoms. Specific examples of the linear or branched alkanoyl group having 8 to 22 carbon atoms, alkenoyl group or hydroxyalkanoyl group include octanoyl group, decanoyl group, dodecanoyl group,
Tetradecanoyl group, hexadecanoyl group, octadecanoyl group, isooctadecanoyl group, hydroxyoctadecanoyl group, eicosanoyl group, behenoyl group, beef tallow fatty acid, hardened tallow fatty acid, palm fatty acid, hardened palm fatty acid, palm stearin Examples of the residue include a residue obtained by removing a hydroxyl group from a fatty acid such as acid and hardened palm stearic acid, preferably a linear alkanoyl group having 8 to 22 carbon atoms, more preferably an octadecanoyl group or a hexadecanoyl group or a mixture thereof. It is an alkanoyl group.

X represents an anionic group, preferably Cl, B
halogen atom such as r, sulfate, carboxylate optionally substituted with a hydroxyl group having 1 to 4 carbon atoms or alkyl sulfate having 1 to 4 carbon atoms (CH ₃ SO ₄ , C ₂ H ₅ SO
₄ etc.), more preferably Cl or CH ₃ SO ₄ , and particularly preferably
Cl.

Examples of preferable quaternary ammonium salts represented by the general formula (1) include the followings.

[0019]

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The quaternary ammonium salt of the present invention represented by the above general formula (1) (hereinafter abbreviated as quaternary ammonium salt (1)) can be produced by the following production method 1.

Production Method 1: General Formula (2)

[0022]

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[In the formula, R ¹ , R ² and R ⁴ have the same meanings as described above. ] And an amino alcohol represented by the general formula (3) R ⁷ Y (3) [wherein, R ⁷ represents a linear or branched alkanoyl group having 8 to 22 carbon atoms, an alkenoyl group or a hydroxyalkanoyl group, Y represents OH, an alkoxy group having 1 to 6 carbon atoms or a halogen atom. ] The general formula (4) obtained by reacting one or more of long-chain fatty acids, fatty acid esters, or fatty acid halides represented by

[0024]

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[In the formula, R ¹ , R ² , R ⁴ , R ⁵ and R ⁶ have the same meanings as described above. ] The amino ester represented by
(5) R ³ X (5) [In the formula, R ³ and X have the same meanings as described above. ] A quaternary ammonium salt (1) is obtained by reacting with a quaternizing agent represented by the following formula, and salt exchange is carried out if necessary.

The details of the method for producing the quaternary ammonium salt (1) will be described below. First, an amino alcohol represented by the general formula (2) (hereinafter abbreviated as amino alcohol (2)) and a long chain fatty acid, a fatty acid ester or a fatty acid halide represented by the general formula (3) A chain fatty acid or its derivative (3) is reacted to obtain an amino ester represented by the general formula (4) (hereinafter abbreviated as amino ester (4)).

The amino alcohol (2) used here is 2-dimethylamino-1,3-propanediol, 2-dimethylamino-2-methyl-1,3-propanediol, 2-dimethylamino-2. -Ethyl-1,3
-Propanediol, 2-diethylamino-1,3-propanediol, 2-diethylamino-2-methyl-
1,3-propanediol, 2-diethylamino-2-
Ethyl-1,3-propanediol, 2-dihydroxyethylamino-1,3-propanediol, 2-dihydroxyethylamino-2-methyl-1,3-propanediol, 2-dihydroxyethylamino-2-ethyl-
1,3-propanediol etc. can be mentioned.

As this amino alcohol (2), a commercially available product may be used as it is, or 2-amino-1,3
-Propanediol may be prepared by alkylation by an existing alkylation method such as a Leukart method or a reductive methylation method. In the case of 2-dihydroxyalkylamino-1,3-propanediol, it may be prepared by adding alkylene oxide to 2-amino-1,3-propanediol. Furthermore, JP-A-53-135948
It can also be obtained by reacting 2-amino-1,3-propanediol with formalin according to the method disclosed in the publication.

Examples of the long chain fatty acid or its derivative (3) used in the present invention include octanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, isooctadecanoic acid, hydroxyoctadecanoic acid, eicosanoic acid, Examples thereof include behenic acid, tallow fatty acid, hardened beef tallow fatty acid, palm fatty acid, hardened palm fatty acid, palm stearic acid, hardened palm stearic acid, and other fatty acids, and their methyl esters, ethyl esters, and fatty acid chlorides.

When the amino alcohol (2) is reacted with the long-chain fatty acid or its derivative (3), the reaction temperature in the esterification reaction is preferably 80 to 240 ° C. in the case of fatty acid,
More preferably, it is 100 to 200 ° C. When a fatty acid ester is used, the temperature is preferably 50 to 240 ° C, more preferably 80 to 200 ° C. 0 if fatty acid halide is used
The temperature is preferably up to 200 ° C, more preferably 10 to 100 ° C. When the reaction temperature is within this range, a product with little coloration can be obtained with an appropriate yield, which is preferable. When fatty acid or fatty acid ester is used, a catalyst may be used to accelerate dealcoholization. As the catalyst at this time, a general esterification catalyst can be mentioned, and an alkali catalyst, a metal catalyst or the like is used. Further, when a fatty acid halide is used, an alkali trap agent may be used for the purpose of trapping hydrogen halide generated.

The molar ratio of [long-chain fatty acid or its derivative (3) / amino alcohol (2)] in this esterification reaction is preferably 1/1 to 4/1, more preferably 1.5 /
It is 1-3 / 1. Within this range, amino alcohols
(2) and the long-chain fatty acid or its derivative (3) are preferable because they remain little in the reaction system.

The reaction pressure may be either normal pressure or reduced pressure, but a reduced pressure reaction is preferable in order to efficiently remove by-produced water or lower alcohol. Specifically, 5 to 400 mmHg,
More preferably, it is 10 to 200 mmHg. When the value indicating the reaction pressure is 5 mmHg or more, there is no risk of unreacted aminoalcohol (2) or long chain fatty acid or its derivative (3) being excluded from the system during the reaction, and it is generated at 400 mmHg or less. It is preferable because the yield of amino ester (4) does not decrease.

Amino ester obtained as described above
(4) is a new compound. Representative compounds of amino ester (4) are exemplified below.

[0034]

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In this reaction, amino alcohol
When a compound in which R ¹ and / or R ² is a hydroxyalkyl group having 1 to 6 carbon atoms is used as (2), the hydroxyalkyl group is acylated with a long chain fatty acid or its derivative (3). The following compounds are by-produced.

[0036]

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Such by-products can be purified and removed by crystallization, chromatography or the like, but if there is no particular problem, the following quaternization reaction may be carried out as it is.

In the quaternization reaction, the amino ester (4) obtained above is quaternized with a quaternizing agent represented by the general formula (5) (hereinafter abbreviated as quaternizing agent (5)). Is a reaction to obtain a quaternary ammonium salt (1).

The quaternizing agent (5) used here is
Examples include lower alkyl halides such as methyl chloride and di-lower alkyl sulfates such as dimethyl sulfate. Examples of the solvent for the quaternization reaction include water, methanol, ethanol, isopropyl alcohol, acetone and the like.

The reaction temperature between the amino ester (4) and the quaternizing agent (5) is preferably 70 to 120 ° C. In addition, in this quaternization reaction, [quaternization agent (5) / amino ester (4)]
The molar ratio of is preferably 0.8 to 2.0, more preferably 0.
95 to 1.5. Under these conditions, the quaternization reaction can be completed without solvent or in a solvent for 0.5 to 10 hours to complete the reaction. After that, post-treatment is carried out according to a conventional method, and if necessary, a salt is added using an ion exchange resin or the like. When exchanged, a quaternary ammonium salt (1) having a necessary counter ion can be obtained.

In this quaternization reaction, the above by-products are also quaternized to produce the compounds exemplified below.

[0042]

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Such by-products can be purified and removed by crystallization, chromatography, or the like if there is a problem in use, but they may be used as they are for a hair treatment agent etc. unless there is a particular problem. .

The structure of the quaternary ammonium salt (1) and amino ester (4) of the present invention can be confirmed by infrared absorption spectrum and nuclear magnetic resonance spectrum.

The quaternary ammonium salt (1) of the present invention is a novel surfactant, can impart excellent flexibility to fibers, and is useful as a soft base having excellent biodegradability.
It can also give excellent flexibility and smoothness to hair,
It can also be applied to hair cosmetics.

The hair cosmetic composition of the present invention contains the quaternary ammonium salt (1) as an essential component, and is used as a hair rinse, hair conditioner, hair treatment, hair pack, hair cream, styling lotion, styling mousse, and conditioning. It can be used for mousses, hair mousses, hair sprays, shampoos, non-rinsing conditioning agents, permanent or basic hair colors, perms and the like. In this case, the quaternary ammonium salt (1) of the present invention can be used alone or in combination of two or more, and is contained in the hair cosmetic composition of the present invention in an amount of 0.1% by weight.
It is preferable to blend the above, particularly 0.1 to 20% by weight,
It is preferable to add 0.1 to 10% by weight.

In the hair cosmetic composition of the present invention, in addition to the quaternary ammonium salt (1) of the present invention, oils and fats and silicones can be used alone or in combination. Examples of the oils and fats include higher alcohols having a linear or branched alkyl group or alkenyl group, hydrocarbons such as liquid paraffin, petrolatum, and solid paraffin, liquid lanolin, lanolin derivatives such as lanolin fatty acid, higher fatty acid esters, and higher fatty acids. Examples thereof include fats and oils such as long-chain amidoamine having an alkyl group or an alkenyl group, and animal and vegetable fats and oils such as mink oil and olive oil. Among these, monoglycerides derived from saturated or unsaturated linear or branched fatty acids having 12 to 24 carbon atoms, higher alcohols and higher fatty acids having a linear or branched alkyl group or alkenyl group having 12 to 26 carbon atoms are preferable, Especially oleic acid monoglyceride, palmitic acid monoglyceride, behenic acid monoglyceride, fatty acid monoglyceride such as isostearic acid monoglyceride, higher alcohol such as cetyl alcohol, stearyl alcohol, arachin alcohol, behenyl alcohol, caranavir alcohol, ceryl alcohol, stearic acid, myristic acid, Higher fatty acids such as behenic acid, isostearic acid, 18-methylicosanoic acid and coconut oil fatty acid are preferred.

Examples of silicones include dimethylpolysiloxane, methylphenylpolysiloxane, and various modified silicones such as amino-modified silicone and polyether-modified silicone. When blending these oils and fats and silicones, 0.01% by weight or more is preferably blended in the hair cosmetic composition of the present invention, particularly 0.01 to 30% by weight,
Further, it is preferable to add 0.05 to 20% by weight.

In the hair cosmetic composition of the present invention, in addition to the above-mentioned components, conventional mono- or di- (long-chain alkyl) may be added, if necessary.
Cationic activators such as quaternary ammonium salts, nonionic activators, humectants such as glycerin and urea, cationic polymers, polymeric substances such as polysaccharides and polypeptides, α
-Hydroxycarboxylic acids, aromatic sulfonic acids, dyes, fragrances, propellants, solvents, chelating agents, pH adjusters, preservatives, anti-dandruff agents, etc. can be appropriately blended within the range not impairing the object of the present invention. .

[0050]

[Examples] The present invention will be described in more detail below with reference to production examples of the quaternary ammonium salt (1) of the present invention and formulation examples of the hair cosmetics of the present invention. However, it is not limited to the prescription example.

Example 1 In a 1-liter 4-necked flask equipped with a stirrer, a thermometer, and a distillation column, 119 g (1.0 mol) of 2-dimethylamino-1,3-propanediol and 596 g (2.1 mol) of octadecanoic acid. Was charged and stirred at 180 ° C. The reaction was carried out while distilling off water produced during the reaction in a distillation column. After confirming the disappearance of 2-dimethylamino-1,3-propanediol in the reaction system after 10 hours by gas chromatography, the reaction system was heated to 200 ° C. and 1 mmHg to remove excess octadecanoic acid. Removed to give 650g of pale yellow solid (yield
97%). The obtained substance was analyzed by IR analysis and NMR, and 2-dimethylamino-1,3- having the following structural formula.
It was confirmed to be di (octadecanoyloxy) propane.

[0052]

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Results of IR analysis and NMR analysis <IR analysis> At 1743 cm ^-1 (5.74 μ), strong absorption peculiar to the ester was observed. <NMR analysis> Solvent CDCl ₃ , internal standard TMS 4.2 ppm (dd, 4H) CC H ₂ -OCO 2.9 ppm (m, 1H) NC H 2.4ppm (s, 6H) C H ₃ -N.

Example 2 The 2-dimethylamino-1, obtained in Example 1, was placed in a 0.5 liter autoclave equipped with a stirrer, a thermometer and a pressure gauge.
100 g of 3-di (octadecanoyloxy) propane, 11 g of methyl chloride and 80 g of isopropyl alcohol were added, and the temperature was raised to 90 ° C. The reaction was terminated by stirring at the same temperature for 6 hours. After the reaction, excess methyl chloride was distilled off,
180 g (yield 98%) of 2-trimethylammonio-1,3-di (octadecanoyloxy) propane chloride having the following structural formula was obtained as a pale yellow solid.

[0055]

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Results of IR analysis and NMR analysis <IR analysis> At 1740 cm ^-1 (5.75 μ), strong absorption peculiar to the ester was observed.

<NMR Analysis> Solvent CDCl ₃ , internal standard TMS 4.6 ppm (dd, 4H) CC H ₂ -OCO 4.5 ppm (m, 1H) NC H 3.6 ppm (s, 9H) C H ₃ -N Example 3 As a raw material amino alcohol, 2-dimethylamino-
A light yellow solid was obtained in the same manner as in Example 1 except that 2-dimethylamino-2-methyl-1,3-propanediol was used instead of 1,3-propanediol (yield 95
%). It was confirmed by the same method as in Example 1 that the obtained compound was 2-dimethylamino-2-methyl-1,3-di (octadecanoyloxy) propane having the following structural formula.

[0058]

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<IR Analysis> At 1743 cm ⁻¹ (5.74 μ), strong absorption peculiar to the ester was observed.

Example 4 2-dimethylamino-2-methyl-obtained in Example 3
1,3-di (octadecanoyloxy) propane 2-
A light yellow solid was obtained in the same manner as in Example 2 except that dimethylamino-1,3-di (octadecanoyloxy) propane was used instead of dimethylamino-1,3-di (octadecanoyloxy) propane (yield 98%). It was confirmed in the same manner as in Example 2 that the obtained compound had the following structural formula.

[0061]

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<IR Analysis> At 1740 cm ⁻¹ (5.73 μ), strong absorption peculiar to the ester was observed.

Example 5 As a raw material amino alcohol, 2-dimethylamino-1,
2-dimethylamino-instead of 3-propanediol
A light yellow solid was obtained in the same manner as in Example 1 except that 2-ethyl-1,3-propanediol was used and hardened tallow fatty acid was used instead of octadecanoic acid (yield 95%). It was confirmed by the same method as in Example 1 that the obtained compound was 2-dimethylamino-2-ethyl-1,3-di (alkanoyloxy) propane having the following structural formula.

[0064]

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(In the formula, R ⁸ represents a residue obtained by removing a carboxyl group from hardened beef tallow fatty acid.) <IR analysis> At 1743 cm ⁻¹ (5.74 μ), strong absorption peculiar to the ester was observed.

Example 6 2-dimethylamino-2-ethyl-obtained in Example 5
The same procedure as in Example 2 was repeated except that 1,3-di (alkanoyloxy) propane was used instead of 2-dimethylamino-1,3-di (octadecanoyloxy) propane,
A pale yellow solid was obtained (98% yield). It was confirmed in the same manner as in Example 2 that the obtained compound had the following structural formula.

[0067]

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(In the formula, R ⁸ has the same meaning as described above.) <IR analysis> At 1740 cm ⁻¹ (5.75 μ), strong absorption peculiar to the ester was observed.

Example 7 The 2-dimethyloxyamino-2-ethyl-1,3-di (alkanoyloxy) propane obtained in Example 5 was replaced with 2 parts.
-Dimethylamino-1,3-di (octadecanoyloxy) propane was used in place of dimethylsulfate in place of methyl chloride to obtain a pale yellow solid (yield 92 %). It was confirmed in the same manner as in Example 2 that the obtained compound had the following structural formula.

[0070]

[Chemical 21]

(In the formula, R ⁸ has the same meaning as described above.) <IR analysis> At 1737 cm ^-1 (5.76 μ), strong absorption peculiar to the ester was observed.

Example 8 As a raw material amino alcohol, 2-dimethylamino-1,
A light yellow solid was obtained in the same manner as in Example 1 except that 2-di (hydroxyethyl) amino-1,3-propanediol was used instead of 3-propanediol (yield 97
%). It was confirmed by the same method as in Example 1 that the obtained compound was 2-di (hydroxyethyl) amino-1,3-di (octadecanoyloxy) propane having the following structural formula.

[0073]

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<IR Analysis> At 1740 cm ⁻¹ (5.73 μ), strong absorption peculiar to the ester was observed.

Example 9 2-di (hydroxyethyl) amino-1,3-di (octadecanoyloxy) propane obtained in Example 8 was replaced with 2 parts.
A light yellow solid was obtained in the same manner as in Example 2 except that it was used instead of -dimethylamino-1,3-di (octadecanoyloxy) propane (yield 95%). It was confirmed in the same manner as in Example 2 that the obtained compound had the following structural formula.

[0076]

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<IR Analysis> At 1737 cm ⁻¹ (5.76 μ), strong absorption peculiar to the ester was observed.

Formulation Example 1 (Hair conditioner) A hair conditioner having the following composition was produced. The obtained hair rinse was able to impart excellent flexibility and smoothness to the hair.

<Composition> Quaternary ammonium salt (Example 2) 1.0 wt% cetyl alcohol 3.0 wt% behenic acid 1.0 wt% diethylene glycol monoethyl ether 3.0 wt% hydroxyethyl cellulose 0.5 wt% water 91.1 wt% fragrance 0.4 wt% prescription Example 2 (styling lotion) A styling lotion having the following composition was produced. The obtained styling lotion was able to impart excellent flexibility and smoothness to hair.

<Composition> Quaternary ammonium salt (Example 4) 0.5% by weight Polyethylene glycol 0.5% by weight Acrylic resin alkanolamine solution 5.0% by weight 2-benzyloxyethanol 1.0% by weight Methacrylic ester polymer 1.0% by weight Ethanol 20.0% by weight % Perfume 0.4% by weight Water balance ─────────────────────────────── 100.0% by weight Formulation 3 (conditioning foam) Composition below A conditioning foam was produced. The obtained conditioning foam was able to impart excellent flexibility and smoothness to hair.

<Composition> Quaternary ammonium salt (Example 6) 0.5% by weight Octyldodecyl myristate 1.0% by weight Dipropylene glycol 1.0% by weight Glycerin 2.5% by weight Liquid paraffin 2.5% by weight Polyoxyethylene monostearate (20) Sorbitan 0.2 wt% Glycolic acid 0.5 wt% Isostearyl pentaerythryl glycidyl ether 1 mol adduct 0.5 wt% Ethanol 5.0 wt% Methylparaben 0.1 wt% Perfume 0.1 wt% Propellant (LPG) 10.0 wt% Water balance ──── ──────────────────────────────── 100.0% by weight

[0082]

The quaternary ammonium salt (1) obtained according to the present invention has flexibility and is easily decomposed by microorganisms. Further, the hair cosmetic composition containing such a quaternary ammonium salt (1) as a main component exhibits excellent flexibility to hair and is mild to skin.

Claims (5)

[Claims] 1. A quaternary ammonium salt represented by the general formula (1). Embedded image [In the formula, R ¹ , R ² and R ³ are the same or different and have 1 to 6 carbon atoms.
A straight-chain or branched alkyl group or a hydroxyalkyl group, R ⁴ is H, a straight-chain or branched alkyl group or a hydroxyalkyl group having 1 to 6 carbon atoms, and R ⁵ and R ⁶ are the same or different and have H or a carbon number. 8 to 22 is a linear or branched alkanoyl group, alkenoyl group or hydroxyalkanoyl group, and at least one of R ⁵ and R ⁶ is a linear or branched alkanoyl group, alkenoyl group or hydroxyalkanoyl group having 8 to 22 carbon atoms. Is. X represents an anionic group. ] 2. In the general formula (1), R ¹ , R ² and R ³ are a methyl group, an ethyl group or a hydroxyethyl group, R ⁴ is H, a methyl group or an ethyl group, and R ⁵ and R ⁶ are carbon atoms. The quaternary ammonium salt according to claim 1, wherein the linear alkanoyl group of 8 to 22 and X is Cl or CH ₃ SO ₄ . 3. A compound of the general formula (2) [In the formula, R ¹ , R ² and R ⁴ have the same meanings as described above. ] And an amino alcohol represented by the general formula (3) R ⁷ Y (3) [wherein, R ⁷ represents a linear or branched alkanoyl group having 8 to 22 carbon atoms, an alkenoyl group or a hydroxyalkanoyl group, Y represents OH, an alkoxy group having 1 to 6 carbon atoms or a halogen atom. ] A long-chain fatty acid represented by the following formula, a fatty acid ester, or one or more kinds of fatty acid halides is reacted to obtain the general formula (4) [In the formula, R ¹ , R ² , R ⁴ , R ⁵ and R ⁶ have the same meanings as described above. ] The amino ester represented by the following general formula (5) R ³ X (5) [In the formula, R ³ and X have the same meanings as described above. ] It reacts with the quaternization agent represented by these, The manufacturing method of the quaternary ammonium salt of Claim 1 characterized by the above-mentioned. 4. An amino ester represented by the general formula (4). Embedded image [In the formula, R ¹ , R ² , R ⁴ , R ⁵ and R ⁶ have the same meanings as described above. ] 5. A hair cosmetic containing the quaternary ammonium salt according to claim 1.