JPH07309724A - Hair cosmetic - Google Patents

Abstract

PURPOSE:To obtain a hair cosmetic which contains a specific quaternary ammo nium salt, thus gives smooth hair dressing results without greasiness, even when it is applied to thin hairs, and further can prevent hairs from tangling with each other on washing. CONSTITUTION:This hair cosmetic contains an ammonium salt of formula I [R<1>, R<2> are alkyl, hydroxyalkyl; R<3>, R<4> are alkylene, alkenylene or hydroxyalkylene; R<5> is formulas II and III (R<8> is H, an alkyl) R<6>, R<7> are alkyl, alkenyl; n is 0-10; X<-> is an anion)], for example, the compound of formula IV, in addition, substances selected from among oils and fats, silicones, solvents, alpha-hydroxymonocarboxylic acid and a liquid crystal-forming base material. The solvent is preferably a compound of formula V (R<28> is H, alkyl; Y, Z are H, OH; g'-j' are 0-5). The liquid crystal-forming substance is preferably selected from glycerylated polyols, branched fatty acid methyl esters and branched fatty acid glyceroglycolipids.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a hair cosmetic composition, and more specifically, it can obtain a smooth finish without stickiness regardless of the quality of hair, and is particularly excellent in preventing entanglement of hair during washing. Regarding hair cosmetics.

[0002]

2. Description of the Related Art Hair cosmetics are required to impart flexibility and smoothness to hair. From such requirements, conventionally, two long-chain alkyl groups in one molecule have been conventionally used. A quaternary ammonium salt having a is used. Examples of such a quaternary ammonium salt include distearyldimethylammonium chloride and di (hardened tallow alkyl).
Dimethyl ammonium salt or the like is used. But,
Hair cosmetics containing these quaternary ammonium salts did not satisfy all of the softness, smoothness and oily feel at the time of washing and drying. There is also a problem that hair is entangled during washing, especially for thin hair.

[0003]

SUMMARY OF THE INVENTION Therefore, the present invention solves the above-mentioned problems and can obtain a smooth finish without stickiness regardless of the hair quality such as thick and thin hair, especially when washing hair. An object of the present invention is to provide a hair cosmetic composition capable of preventing hair entanglement.

[0004]

Under such circumstances, the inventors of the present invention have conducted diligent research and as a result, by using a specific quaternary ammonium salt, even a thin hair has a smooth finish without stickiness. It was found that a hair cosmetic composition capable of obtaining the following can be obtained, and further that the hair can be prevented from being entangled at the time of washing the hair, and the present invention has been completed.

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

[0006]

[Chemical 4]

[In the formula, R ¹ and R ² are the same or different and each represents an alkyl group or a hydroxyalkyl group having 1 to 4 carbon atoms, and R ³ and R ⁴ are the same or different and each have 1 to ⁴ carbon atoms. 5 represents an alkylene group, an alkenylene group or a hydroxyalkylene group, and R ⁵ is represented by the following formula;

[0008]

[Chemical 5]

(R ⁸ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms)
⁵ may be the same or different), R ⁶ and R ⁷ are
The same or different, and represents a linear or branched alkyl group or alkenyl group having 8 to 36 carbon atoms, n represents an integer of 0 to 10, and X ⁻ represents an anion]. The present invention provides a hair cosmetic composition containing an ammonium salt.

Further, in the present invention, in addition to the quaternary ammonium salt, one or more kinds selected from the group consisting of oils and fats, silicones, solvents, α-hydroxymonocarboxylic acid and liquid crystal forming base are further contained. The present invention provides a hair cosmetic composition.

The quaternary ammonium salt used in the present invention is represented by the above general formula (1).

In the formula, the number of carbon atoms represented by R ¹ and R ² is 1 to
Examples of the alkyl group and hydroxyalkyl group of 4 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group,
Examples thereof include a butyl group, and those in which one or more hydroxyl groups are substituted, and an alkyl group having 1 to 2 carbon atoms or a hydroxyalkyl group is preferable, and a methyl group is particularly preferable. Examples of the alkylene group having 1 to 5 carbon atoms represented by R ³ and R ⁴ include a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, and the like, and a hydroxyalkylene group includes one or more hydroxyl groups thereof. Examples thereof include those substituted with a group, and examples of the alkenylene group include ethenylene group, propenylene group, butenylene group and the like. Of these, an alkylene group having 1 to 2 carbon atoms is preferable. As R ⁵ , R ⁸ in the formula is preferably a hydrogen atom or a methyl group, and particularly preferably an ethylene group. 8 to 36 carbon atoms represented by R ⁶ and R ⁷
The alkyl group of, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, eicosyl group, heneicosyl group and these Corresponding branched chain alkyl groups and the like can be mentioned, and as the alkenyl group,
Octenyl group, nonenyl group, decenyl group, undecenyl group, tridecenyl group, tetradecenyl group, pentadecenyl group, hexadecenyl group, heptadecenyl group, octadecenyl group, nonadecenyl group, eicosenyl group, heneeicosenyl group, docosenyl group, tricosenyl group, tetracosenyl group, tetraconcenyl group Examples thereof include a nyl group, a pentatriaconcenyl group, a branched-chain alkenyl group corresponding thereto, and an alkyl group derived from natural fats and oils such as coconut oil, palm oil, beef tallow, rapeseed oil, and fish oil. Of these, an alkyl group or an alkenyl group having 12 to 22 carbon atoms is preferable, and a tetradecyl group, a hexadecyl group, an octadecyl group, an eicosyl group, a tetradecenyl group, a hexadecenyl group, an octadecenyl group, an eicosenyl group, and a docosenyl group are particularly preferable. n represents an integer of 0 to 10,
An integer of 0 to 5 is preferable, and 0 to 2 is particularly preferable. Examples of X ⁻ include halogen ions such as Cl ⁻ and Br ⁻ , alkyl sulfate ions such as CH ₃ SO ₄ ⁻ , and Cl ⁻ is particularly preferable.

Of these quaternary ammonium salts, one of
In general formula (1), R¹And R ²Has 1 to 2 carbon atoms
An alkyl group or a hydroxyalkyl group, R³as well as
R^FourIs an alkylene group having 1 to 2 carbon atoms, and R^FiveIn the formula
R⁸Is a hydrogen atom or a methyl group, and R⁶Over
And R⁷Is a linear or branched alkyl group having 12 to 22 carbon atoms
A group or an alkenyl group, n is an integer of 0 to 5,
X^-Is Cl^-, Br^-Halogen ion such as CH or CH₃SO
_Four ^-Alkylsulfate ion (preferably Cl
^-) Are preferred, and especially R¹And R²Is methyl
Group, R³And R^FourIs an alkylene group having 1 to 2 carbon atoms
And R^FiveIs preferably an ethylene group.

Preferred specific examples of the quaternary ammonium salt represented by the general formula (1) include those represented by the following formula.

[0015]

[Chemical 6]

The quaternary ammonium salt represented by the general formula (1) can be produced, for example, according to the following method.

[0017]

[Chemical 7]

(Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ ,
R ⁶ , R ⁷ , n and X ⁻ have the same meanings as described above, and R ⁹
Represents an alkyl group having 1 to 3 carbon atoms, and Y represents a halogen atom)

That is, the quaternary ammonium salt (1) can be obtained by reacting the amino ester (2) with the amine (3) to obtain amidoamine, and then reacting this with the compound (5).

The reaction between the amino ester (2) and the amine (3) is carried out in the presence of a solvent such as ethanol, isopropanol or toluene, or in the absence of a solvent, in the presence of a catalyst such as sodium hydroxide, potassium hydroxide or sodium methylate. Alternatively, it is preferably carried out without a catalyst. Also, amino ester (2)
The amount of amine (3) to be used is 0.8-
1.5 is preferable, and the reaction temperature is preferably 60 to 150 ° C.

The aminoester (2) used in this reaction is methyl N, N-dimethylaminoacetate,
Methyl N- (2-hydroxyethyl) -N-methylaminoacetate, methyl N, N-bis (2-hydroxyethyl) aminoacetate, methyl N, N-dimethylaminopropionate, N- (2-hydroxyethyl)- Methyl N-methylaminopropionate, methyl N, N-bis (2-hydroxyethyl) aminopropionate, methyl N, N-dimethylaminobutyrate, N- (2-hydroxyethyl) -N-
Methyl methylaminobutyrate, N, N-bis (2-hydroxyethyl) -methyl aminobutyrate, methyl N, N-dimethylaminocaproate, N- (2-hydroxyethyl)-
Methyl N-methylaminocaproate, N, N-bis (2
-Hydroxyethyl) aminocaproic acid methyl or their ethyl ester, propyl ester and the like can be mentioned.

As the amine (3), octylamine, decylamine, dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, eicosylamine, docosylamine, 2-ethylhexylamine, 2-butyloctylamine, 2- Hexyldecylamine, 2-octyldodecylamine, 2-decyltetradecylamine, 2-dodecylhexadecylamine, 2
Mention may be made of tetradecyl octadecyl amine, 2-hexadecyl eicosyl amine, oleyl amine, elaidyl amine and mixtures thereof.

Further, amidoamine (4) and compound (5)
The reaction of is preferably carried out at 40 to 130 ° C. in the presence of a solvent such as ethanol, isopropanol and acetone.
The amount of the compound (5) used with respect to the amidoamine (4) is preferably 0.8 to 1.5 in terms of molar ratio.

As the compound (5) used in this reaction, for example, JP-A-56-10153, page 4, page 1
It can be produced by reacting a halocarboxylic acid or a corresponding halocarboxylic acid chloride with an alcohol or an alkylene oxide adduct thereof, as described in Column 2, Line 10 to Column 13, Line 12. Examples of the halocarboxylic acid used here include chloroacetic acid, chloropropionic acid, chlorobutyric acid, and chlorocaproic acid. Further, as the alcohol, octanol, decanol, dodecanol, tetradecanol, hexadecanol, octadecanol, eicosanol,
Docosanol, 2-ethylhexanol, 2-butyloctanol, 2-hexyldecanol, 2-octyldodecanol, 2-decyltetradecanol, 2-dodecylhexadecanol, 2-tetradecyloctadecanol, 2-hexadecyleicosa Examples thereof include nols, oleyl alcohol, elaidyl alcohol and mixtures thereof. Further, examples of alkylene oxide adducts of these alcohols include propylene oxide adducts and random or block adducts of ethylene oxide and propylene oxide.

The quaternary ammonium salt (1) thus obtained may contain an ion exchange resin or the like, if necessary.
The counter ion can be exchanged with the above-mentioned halogen ion or alkyl sulfate ion.

These quaternary ammonium salts may be used either individually or in combination of two or more. It is preferable to add 0.1% by weight or more to the total composition, especially 0.1 to 0.1% by weight.
It is preferable to add 20% by weight, more preferably 0.1 to 10% by weight.

The hair cosmetic composition of the present invention may contain amidoamine (4), which is a production intermediate in the above reaction formula, in order to impart flexibility. As the amidoamine (4), the remaining unreacted product can be used as it is as a cosmetic ingredient. Examples of this amidoamine include those represented by the following formula.

[0028]

[Chemical 8]

(In the formula, R ³⁴ represents an alkyl group having a composition obtained by substituting the carboxyl group of hardened tallow fatty acid with a methylene group, and R ³⁵ is obtained by substituting the carboxyl group of hardened palm oil fatty acid with a methylene group. And R ³⁶ represents an oleyl group.)

The hair cosmetic composition of the present invention may further contain one or more selected from the group consisting of oils and fats, silicones, solvents, α-hydroxymonocarboxylic acid and liquid crystal forming bases. By compounding, the effect of the present invention can be further enhanced. These components may be used alone or in appropriate combination of two or more in consideration of the properties of each.

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, and higher fatty acids. Examples thereof include esters, higher fatty acids, 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, carbon number 12-24
Saturated or unsaturated linear or branched fatty acid-derived monoglyceride, higher alcohols and higher fatty acids having a linear or branched alkyl or alkenyl group having 12 to 26 carbon atoms are preferable, and oleic acid monoglyceride is particularly preferable.
Palmitic acid monoglyceride, behenic acid monoglyceride, fatty acid monoglyceride such as isostearic acid monoglyceride, cetyl alcohol, stearyl alcohol,
Higher alcohols such as araquin alcohol, behenyl alcohol, caranavir alcohol and ceryl alcohol,
Higher fatty acids such as stearic acid, myristic acid, behenic acid, isostearic acid, 18-methylicosanoic acid and coconut oil fatty acid are preferred.

When fats and oils are blended, 0.01 wt% or more is preferably blended in the entire composition, and especially 0.0
It is preferable to add 1 to 30% by weight, more preferably 0.05 to 20% by weight.

Examples of silicones include the following (1)
~ (10) are mentioned. (1) A dimethylpolysiloxane represented by the following formula (6).

[0034]

[Chemical 9]

(In the formula, a represents a number of 3 to 20,000.) (2) A methylphenylpolysiloxane represented by the following formula (7) or (8).

[0036]

[Chemical 10]

(In the formula, b is a number of 1 to 20,000, and c and d are numbers such that the sum thereof is 1 to 500.) (3) Amino represented by the following formula (9) or (10) Modified silicone.

[0038]

[Chemical 11]

Of these, particularly preferred amino-modified silicones are represented by the following general formula.

[0040]

[Chemical 12]

(In the formula, R ¹² , e and f have the above-mentioned meanings.) A preferred amino-modified silicone used in the present invention is represented by the following general formula and has an average molecular weight of about 300.
0-100000, which is CTFA under the name of Amodimethicone
Dictionary (US, Cosmetic Ingredient
Dictionary) 3rd edition.

[0042]

[Chemical 13]

(In the formula, e and f have the above-mentioned meanings.) The above amino-modified silicone is preferably used as an aqueous emulsion, and the aqueous emulsion is, for example, JP-B-56-
According to the method described in Japanese Patent No. 38609, a cyclic diorganopolysiloxane and an organodialkoxysilane having an aminoalkyl group and a hydroxyl group, a hydroxyalkyl group, an oxyalkylene group or a polyoxyalkylene group are combined with a quaternary ammonium salt. It can be obtained by emulsion polymerization in the presence of a system surfactant and water.

When the above amino-modified silicone is used as an aqueous emulsion, the amount of amino-modified silicone contained in the aqueous emulsion is usually 20 to 60% by weight, preferably 30 to 50% by weight. is there.

Examples of commercially available amino modified silicone aqueous emulsions include SM 8702C (manufactured by Toray Silicone Co., Ltd.) and DC 929 (manufactured by Dow Corning Co., Ltd.).

(4) A fatty acid-modified polysiloxane represented by the following formula (11).

[0047]

[Chemical 14]

[Wherein j, k and l are numbers from 1 to 350]
, M is a number from 0 to 10, R¹⁸Is C _nH_{2n + 1}(N =
9 to 21). ] (5) An alcohol represented by the following formula (12) or (13)
Modified silicone.

[0049]

[Chemical 15]

[In the formula, o and p each represent a number of 1 to 500 (preferably 1 to 200), and R ¹⁹ represents C _q H _2q (q =
0-4) is shown. (6) An aliphatic alcohol-modified polysiloxane represented by the following formula (14).

[0051]

[Chemical 16]

[In the formula, R ²⁰ represents a methyl group or a phenyl group, r represents an integer of 1 to 3000, and s and t represent s +.
t is an integer of 1 to 500, and R ²¹ has 1 to 2 carbon atoms.
8 represents an alkyl group having 8 to 12 carbon atoms (preferably 12 to 22 carbon atoms), and u represents an integer of 0 to 6. ] (7) The following formulas (15), (16), (17) or (1
A polyether-modified silicone represented by 8).

[0053]

[Chemical 17]

(8) An epoxy-modified silicone represented by the following formula (19).

[0055]

[Chemical 18]

[Wherein a'is 1 to 500 (preferably 1
~ 250), b'is 1 to 50 (preferably 1 to 3)
0) and R ²³ represents an alkylene group having 1 to 3 carbon atoms. (9) A fluorine-modified silicone represented by the following formula (20).

[0057]

[Chemical 19]

[Wherein c'is 1 to 400 (preferably 1
.About.250). ] (10) Cyclic silicone represented by the following formula (21).

[0059]

[Chemical 20]

[In the formula, d ′ represents a number of 3 to 8 and R ²⁴ represents an alkyl group having 1 to 3 carbon atoms. (11) An alkyl-modified silicone represented by the following formula (22) or (23).

[0061]

[Chemical 21]

In these silicones, rinse,
In the case of a rinse-type hair cosmetic such as a conditioner, in the above (1) [wherein, a can be selected from 3 to 20,000 depending on the purpose of the feeling of finish, but a light finish type Is preferably about 100 to 1000], (3), (6), (7) and (10).
Are preferred. Further, in the case of a soothing type hair cosmetic such as a hair cream, a styling lotion, or a styling mousse, in the formula (6), for the purpose of reducing oily feeling, a Is 2000
To 8000 are preferable], (2), (3),
Those of (7) and (10) are preferable.

When blending these silicones,
These can be used alone or in combination of two or more, and it is preferable to add 0.01% by weight or more to the whole composition, particularly 0.01 to 20% by weight, and further 0.1 to 10% by weight. It is preferable to mix them.

Examples of the solvent include compounds represented by the following formula (24).

[0065]

[Chemical formula 22]

Specific examples of these solvents include ethanol, isopropanol, n-propanol, n-butanol, isobutanol, ethylene glycol, propylene glycol, 1,3-butanediol, benzyl alcohol, cinnamyl alcohol, phenethyl alcohol, p-anisyl alcohol, p-methylbenzyl alcohol, phenoxyethanol, 2-benzyloxyethanol, methylcarbitol, ethylcarbitol,
Propyl carbitol, butyl carbitol, glycerin, N-methylpyrrolidone, N-octylpyrrolidone,
N-laurylpyrrolidone, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monobutyl ether, diethylene glycol monopentyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monot
-Butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopentyl ether, dipropylene glycol monoisopropyl ether, dipropylene glycol mono t-butyl ether , Triethylene glycol monoethyl ether, triethylene glycol monobutyl ether, and the like.

As the solvent, ethanol, isopropanol, propylene glycol, glycerin, benzyl alcohol, 2-benzyloxyethanol, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether and dipropylene glycol monopropyl ether are particularly preferable.

When a solvent is added, it may be added in an amount of 0.
It is preferable to add 1% by weight or more, particularly 0.1 to 90
It is preferable to add 0.5% by weight, more preferably 0.5 to 50% by weight.

The α-hydroxymonocarboxylic acid or its salt is represented by the following formula (25)

[0070]

[Chemical formula 23]

(In the formula, R ³¹ represents a hydrogen atom or a C 1-3 carbon atom.
Which represents an alkyl group of), and specific examples thereof include glycolic acid, lactic acid, α-hydroxybutyric acid, and the like. Examples of the salt include sodium salt, potassium salt, calcium salt, ammonium salt, triethanolamine salt, organic quaternary ammonium salt and the like. Of these, glycolic acid and salts thereof are preferable because they are particularly excellent in the effect of imparting flexibility and the effect of preventing entanglement of hair during washing.

When the α-hydroxymonocarboxylic acid is blended, it is preferably blended in an amount of 0.1% by weight or more, particularly 0.1 to 90% by weight, and further 0.5 to 50% by weight in the entire composition. Preferably.

Examples of the liquid crystal forming base include those having at least one long-chain branched alkyl group or alkenyl group and at least three hydroxyl groups in one molecule, and the lamellar at temperatures above 25 ° C and 50 ° C. Those retaining a crystal structure are preferable. In particular,
Preference is given to (a) glycerylated polyols, (b) methyl branched fatty acid ester, (c) branched fatty acid glyceroglycolipid and the like.

The glycerylated polyols (a) are represented by the following general formula: A _x (G) [wherein G is X from a polyol selected from pentaerythritol, sorbitol, maltitol, glucose, fructose and alkyl glycosides]. Is a residue excluding the hydroxyl group of

[0075]

[Chemical formula 24]

(Wherein R ³² represents a branched alkyl group or alkenyl group having 10 to 36 carbon atoms), x is a number of 1 or more, and does not exceed the total number of hydroxyl groups of the polyol] Can be mentioned.

Examples of the alkyl glycoside represented by G include methyl glycoside, ethyl glycoside, propyl glycoside, octyl glycoside, methyl maltoside, ethyl maltoside and the like. Also,
R ¹¹ is preferably a branched alkyl group having 16 to 36 carbon atoms, and more preferably a branched alkyl group having 18 to 24 carbon atoms. Examples of such branched alkyl groups include the following formulas;

[0078]

[Chemical 25]

(In the formula, j'and k'are 0 to 20 respectively.
Is an integer such that the sum of j'and k'is 6 to 20) or the following formula;

[0080]

[Chemical formula 26]

(In the formula, l'and m'are 0 to 18 respectively.
And a sum of l ′ and m ′ is 4 to 18), and specific examples thereof include a methylpentadecyl group, a methylhexadecyl group, and a methylheptadecyl group. (Isostearyl) group, methyloctadecyl group, methylbehenyl group, ethylhexadecyl group,
Ethyl octadecyl group, ethyl behenyl group, butyl dodecyl group, butyl hexadecyl group, butyl octadecyl group, hexyl decyl group, heptyl undecyl group, octyl dodecyl group, decyl dodecyl group, decyl tetradecyl group, dodecyl hexadecyl group, tetradecyl group An octadecyl group etc. can be mentioned. Moreover, as x, 1 or 2 is preferable.

(B) Methyl branched fatty acid ester has the following formula;

[0083]

[Chemical 27]

(In the formula, n'and o'are 0 to 20 respectively.
In which the sum of n'and o'is 1 to 20). Where n '
The sum of and o'is preferably 10 to 16, and more preferably 14. The branched methyl group is preferably located near the center of the alkyl main chain.

The branched fatty acid glyceroglycolipid (c) has the following formula:

[0086]

[Chemical 28]

(Here, p'and q'are 0 to 20 respectively.
Is an integer such that the sum of p'and q'is 6 to 20, r'and s'are integers of 0 to 18, respectively, and the sum of r'and s'is 4 to 18. And a group represented by the following). Here, the sum of p'and q'is preferably 10 to 16, and more preferably 14. The sum of r'and s'is preferably 10 to 16, and more preferably 14.

When these liquid crystal forming bases are blended, 0.01 wt% or more is preferably blended in the entire composition, particularly 0.1-60 wt%, and further 0.1-30 wt%.
It is preferable to mix them.

When two or more kinds of oil agent, silicones, solvent, α-hydroxymonocarboxylic acid and liquid crystal base are used in combination, the total amount thereof is 0.05 to 90.
%, Especially 0.1 to 50% by weight is preferred.

In addition to the above-mentioned components, the hair cosmetic composition of the present invention may contain conventional mono- or di- (long-chain alkyl), if necessary.
Cationic activators such as quaternary ammonium salts, nonionic activators, moisturizers such as glycerin and urea, cationic polymers, polymeric substances such as polysaccharides and polypeptides, aromatic sulfonic acids, dyes, fragrances, sprays Agent, chelating agent,
A pH adjusting agent, an antiseptic agent, an anti-dandruff agent and the like can be appropriately added within a range that does not impair the object of the present invention.

The hair cosmetic composition of the present invention can be manufactured by a conventional method. The dosage form is not particularly limited and may be a desired dosage form such as an aqueous solution, an ethanol solution, an emulsion, a suspension, a gel, a liquid crystal, a solid or an aerosol.

The hair cosmetic composition of the present invention comprises a hair rinse, a hair conditioner, a hair treatment, a hair pack,
It can be used for heme cream, styling lotion, styling mousse, conditioning mousse, hair mousse, hair spray, shampoo, non-rinsing conditioning agent, permanent or basic hair color, perm agent and the like.

[0093]

Since the hair cosmetic composition of the present invention contains the quaternary ammonium salt represented by the general formula (1), it can achieve a smooth finish without stickiness regardless of hair quality. Especially, the effect of preventing entanglement of hair during washing is excellent. Further, in addition to the quaternary ammonium salt, 1 selected from the group consisting of oils and fats, silicones, solvents, α-hydroxymonocarboxylic acid and liquid crystal forming bases.
By blending more than one species, the above effects can be further enhanced.

[0094]

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

Synthesis Example 1 Octadecylamine (179 g) and N, N-dimethylaminomethylacetate (86 g) were placed in a four-necked flask equipped with a stirrer, a thermometer and a condenser, and the temperature was raised to 110 ° C. The reaction was carried out at the same temperature for 20 hours. Recrystallized from acetone,
200 g of amidoamine was obtained. Next, stirrer, thermometer,
The above-mentioned amidoamine 57 was placed in a four-necked flask equipped with a cooling tube.
g, acetone 400 ml, octadecyl chloroacetate 60
g was added and the mixture was reacted at 55 ° C. for 10 hours. The precipitated crystals were collected by filtration and dried to obtain 80 g of the target compound (1-1) represented by the following structural formula. Its structure was confirmed from the NMR spectrum and IR spectrum.

[0096]

[Chemical 29]

[0097]

[Chemical 30]

IR spectrum (KBr tablet method) 1761 cm ^-1 , 1677 cm ^-1 , 1578 cm ^-1

Synthesis Examples 2 to 10 In the same manner as in Synthesis Example 1, target compounds 1-2 to 1-10 were obtained. These are summarized in Table 1. In the formulas in Table 1, R ³⁷ and R ³⁸ represent an alkyl group having a composition obtained by substituting the carboxyl group of hardened beef tallow fatty acid with a methylene group, and R ³⁹ and R ⁴⁰ represent the carboxyl group of hardened palm oil fatty acid. Shows an alkyl group having a composition obtained by substituting a methylene group.

[0100]

[Table 1]

Example 1 Hair rinses having the compositions shown in Tables 2 to 7 (Products 1 to 1 of the invention)
4 and comparative products 1-2) were produced by a conventional method. The obtained hair rinse agent was subjected to sensory evaluation of smoothness and the like by the following method. The results are shown in Tables 2 to 7.

(Evaluation method) 25 g of hair of a Japanese woman (length 15 c) that has not been chemically treated with cold perm or the like.
m, average diameter 60 μm), and hair rinsing agent 2.5 g
Was evenly applied and then rinsed under running water for 30 seconds. Then, it was towel dried and further dried with a dryer. The dried hair tresses were evaluated for smoothness and non-stickiness according to the following criteria. Further, the hair bundle after the evaluation was washed with a commercially available shampoo mainly containing an anion activator, and the entanglement of the hair in that case was evaluated according to the following criteria.

Smoothness: Good: Smooth. Δ: Neither can be said. X: Not smooth Sticky feeling; Good: little. Δ: Neither can be said. X: Many. Ease of entanglement of hair during the next shampoo; ◯: Difficult to entangle. Δ: Neither can be said. X: Easy to get entangled.

[0104]

[Table 2]

[0105]

[Table 3]

[0106]

[Table 4]

[0107]

[Table 5]

[0108]

[Table 6]

[0109]

[Table 7]

Example 2 A hair rinse agent (Invention product 15 and Comparative product 3) having the following composition was produced by a conventional method.

(Invention product 15) (wt%) quaternary ammonium salt (1-2) 1.0 cetyl alcohol 3.0 behenic acid 1.0 diethylene glycol monoethyl ether 3.0 hydroxyethyl cellulose 0.5 water 91.1 Fragrance 0.4 (Comparative Product 3) (% by weight) Stearyl trimethylammonium chloride 1.0 Cetyl alcohol 3.0 Behenic acid 1.0 Diethylene glycol monoethyl ether 3.0 Hydroxyethyl cellulose 0.5 Water 91.1 Fragrance 0.4

Using these hair rinse agents, the rinsing performance was evaluated by the paired comparison method for the hair of 10 panelists who were permed. The comparison criteria are shown as +2 when it is very good and +1 when it is good, and the number of persons corresponding to each is displayed. The results are shown in Table 9.

[0112]

[Table 9]

Example 3 Hair rinse agent having the composition shown in Table 10 (Products 16 to 1 of the present invention)
8) was produced by a conventional method.

[0114]

[Table 10]

Example 4 Shampoos having the compositions shown in Table 11 (Products 19 to 24 of the present invention)
Was produced by a conventional method.

[0116]

[Table 11]

With these shampoos, the hair was not tangled during washing, and the feel after drying was also smooth.

Example 5 (Styling lotion) A styling lotion having the following composition was produced.

Table 12 (Components) (% by weight) Quaternary ammonium salt (1-6) 0.5 Polyethylene glycol 0.5 Acrylic resin Alkanolamine liquid 5.0 2-Benzyloxyethanol 1.0 Methacrylic ester polymer 1 0.0 ethanol 20.0 fragrance 0.4 water balance 100.0

Example 6 (conditioning foam)

Table 13 (Components) (wt%) Quaternary ammonium salt (1-7) 0.5 Octyldodecyl myristate 1.0 Dipropylene glycol 1.0 Glycerin 2.5 Liquid paraffin 2.5 Monostearate poly Oxyethylene (20) sorbitan 0.2 Glycolic acid 0.5 Isostearyl pentaerythryl glycidyl ether 1 mol adduct 0.5 Ethanol 5.0 Methylparaben 0.1 Perfume 0.1 Propellant (LPG) 10.0 Water Balance 100.0

Example 7 (Hair Cream)

[Table 14] (Components) (% by weight) Quaternary ammonium salt (1-8) 2.0 Cetyl trimethyl ammonium chloride 1.0 Polyoxyethylene monostearate (20) sorbitan 0.5 Cetyl alcohol 5.0 Iso Stearyl pentaerythryl glycidyl ether 1 mol adduct 0.5 Behenic acid 1.0 Dipropylene glycol 6.0 Glycerin 10.0 Liquid paraffin 3.0 Perfume 0.4 Water balance 100.0

Example 8 (First agent for permanent hair dye)

Table 15 (Components) (wt%) Paraphenylenediamine 2.0 2,4-Diaminoanisole 1.0 Resorcin 0.2 Oleic acid 10.0 Polyoxyethylene (10) oleyl ether 15.0 Quaternary ammonium Salt (1-1) 1.0 Propylene glycol 10.0 Ammonia water (28%) 6.0 Water Balance Frost DS (EDTA2Na) 0.5 100.0

Example 9 (Permanent Wave First Agent)

Table 16 (Components) (% by weight) Ammonium thioglycolate 6.0 18-Methylicosanoic acid 1.0 Ammonia water (28%) 3.0 Frost DS (EDTA2Na) 0.5 2-Benzyloxyethanol 10.0 Quaternary ammonium salt (1-2) 2.0 Water balance 100.0

Example 10 (Second wave of permanent wave)

Table 17 (Component) (wt%) Sodium bromate 8.0 Quaternary ammonium salt (1-2) 2.0 Isostearate 0.5 2-Benzyloxyethanol 5.0 Water Balance 100.0

The hair cosmetics obtained in Examples 3 to 10 were
All of them were able to obtain a smooth finish without stickiness, and were particularly excellent in the effect of preventing entanglement of hair during washing.

Claims (6)

[Claims] 1. The following general formula (1): [In the formula, R ¹ and R ² are the same or different and each has 1 carbon atom.
~ 4 alkyl group or hydroxyalkyl group, R
³ and R ⁴ are the same or different and each represents an alkylene group having 1 to 5 carbon atoms, an alkenylene group or a hydroxyalkylene group, and R ⁵ is represented by the following formula: (R ⁸ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms) (provided that n R ^{5 s} may be the same or different), and R ⁶ and R ⁷ are The same or different, and represents a linear or branched alkyl group or alkenyl group having 8 to 36 carbon atoms, n represents an integer of 0 to 10,
X ⁻ represents an anion], wherein the hair cosmetic composition comprises a quaternary ammonium salt. 2. Further, oils and fats, silicones, solvents, α
The hair cosmetic composition according to claim 1, which contains at least one member selected from the group consisting of hydroxymonocarboxylic acid and a liquid crystal forming base. 3. The solvent is represented by the following formula: The hair cosmetic composition according to claim 2, which is represented by 4. The liquid crystal forming base has at least one long-chain branched alkyl or alkenyl group and at least three hydroxyl groups in one molecule.
Or the hair cosmetic composition according to item 3. 5. A liquid crystal forming base material having at least one long-chain branched alkyl group or alkenyl group and at least three hydroxyl groups in one molecule and having a lamellar crystal structure at a temperature above 25 ° C. and 50 ° C. The hair cosmetic composition according to claim 2 or 3, which holds 6. The hair cosmetic composition according to claim 2, wherein the liquid crystal forming base is selected from glycerylated polyols, methyl branched fatty acid esters and branched fatty acid glyceroglycolipids.