JPH1072323A - Hair cosmetic - Google Patents

Abstract

PROBLEM TO BE SOLVED: To prepare a hair cosmetic that has excellent adhesive property and compatibility with different base materials, good water solubility, and provides a film having excellent hair setting force and feeling by compounding a specific amine oxide-containing water-soluble resin. SOLUTION: This hair cosmetic contains an amine oxide-containing water-soluble resin of weight-average molecular weight ranging from 5000 to 100,000 obtained by polymerizing (A) 15-100wt.% of hydrophilic monomers, including amine oxide-containing monomers, and (B) 85-0wt.% of hydrophobic monomers. Component (A) is preferably a compound of formula I (R<1> is H or methyl, R<2> and R<3> are each an alkyl, an aryl or an arylalky; (m) is 0-1) or formula II (R<4> is an alkyl, an aryl, etc.; (n) is 0-4). This amine oxide-containing water-soluble resin is added to shampoos, rinses, hair treatments, hair setting agents, permanent wave liquids, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a hair cosmetic containing an amine oxide group-containing water-soluble resin. The hair cosmetic composition of the present invention has excellent adhesion to hair, compatibility with various base materials, good water solubility, and gives a film having excellent hair setting power and texture.

[0002]

2. Description of the Related Art It is well known to fix hair to a desired shape by fixing it with a resin. Nonionic, anionic and cationic resins are used as such hair cosmetic resins. Polyvinyl methyl ether, polyvinyl pyrrolidone, and the like are used as the nonionic resin, and polyvinylipyrrolidone is easily affected by humidity conditions. In other words, the film before moisture absorption is hard and easily causes a flaking phenomenon, but at high temperature and high humidity, it becomes very flexible and causes a blocking phenomenon, and the hairs may stick to each other and combing or brushing may not be possible. is there. In the case of polyvinyl methyl ether, the influence of such humidity is even more remarkable.

The anionic resin includes a copolymer of vinyl carboxylic acid, for example, acrylic acid, methacrylic acid or the like as an ionic group, and vinyl carboxylic acid and styrene, alkyl acrylate or the like. Unlike the nonionic resin, the anionic resin is hardly affected by humidity, but has the same anionic property as the hair and thus has a low affinity for the hair. In general, a film of an anionic resin is hard and has a high hair-dressing effect, but is brittle and may cause a flaking phenomenon. Furthermore, the addition of a cationic substance is restricted by being anionic, and there is a concern about a solidification phenomenon due to a rinsing agent (cationic) during hair washing.

[0004] Cationic resins have a greater affinity for hair than the former two, but are susceptible to humidity as well as nonionic resins. In addition, there is concern about toxicity and skin irritation due to being cationic, addition of an anionic substance is restricted, and solidification by shampoo (anionic) during hair washing is also a problem. Further, the resin used is easily removable by washing hair, is easily diluted with water at the time of preparing hair cosmetics, and alcohol-free hair cosmetics are being demanded from the viewpoint of environmental problems. Is preferably water-soluble. However, generally, there has been a problem that increasing the water solubility of the resin lowers the setting force. To improve the drawbacks of hair cosmetics containing these anionic resin, cationic resin and nonionic resin, it has been proposed to use an amphoteric ionic polymer which is a copolymer having a carboxybetaine moiety as a hydrophilic group. .
This zwitterionic polymer is known as a hair styling polymer excellent in terms of affinity with hair and performance such as setting power, and a tertiary amine-containing (meth) acrylic acid ester (hereinafter, referred to as (meth) acrylic acid). Is a term collectively expressing acrylic acid and methacrylic acid.)-Based unsaturated monomer (a) having an alkyl group having 1 to 4 carbon atoms (meth)
Acrylic acid alkyl ester (b) and carbon number of 12 to 1
A hair styling resin comprising a zwitterionic polymer obtained by amphoteric ionizing a terpolymer with a (meth) acrylic acid alkyl ester (c) having an alkyl group of 8 with a halogenated acetate (Japanese Patent Application Laid-Open No. 51-1979) 9732, JP-A-55
See -104209. )

[0005]

However, the zwitterionic polymer is not sufficiently compatible with various cosmetic base materials, for example, an anionic surfactant. Particularly, the compatibility with the gel base material is poor.

As described above, the conventional resins cannot always satisfy all the performances. The present invention solves the problems of the conventional cosmetic base material for hair, particularly the zwitterionic polymer, and solves the problem that it is difficult to dilute with water when preparing hair cosmetics. It is intended to provide a hair cosmetic having sufficient hair washing properties and good hair styling properties when used by application.

[0007]

SUMMARY OF THE INVENTION The gist of the present invention is a hair cosmetic containing a water-soluble resin containing an amine oxide group having a weight average molecular weight of 5,000 to 1,000,000. Amine oxide group-containing resins include (1) one kind of amine oxide group-containing monomer (2). Two or more kinds of amine oxide group-containing monomers (3). It can be obtained by polymerizing or copolymerizing another hydrophilic monomer (4). Any of (1) to (3) and a hydrophobic monomer. Preferably, the proportion of the amine oxide group-containing monomer in all the monomers used for the water-soluble resin of the present invention is 30%.
% By weight or more. In the case of (4), the hydrophobic monomer is copolymerized within a range that does not impair the water solubility of the resin. Further, it can also be obtained by using a nitrogen-containing precursor monomer instead of the amine oxide group-containing monomer, and polymerizing or copolymerizing this, followed by oxidization. Furthermore, it can also be obtained by polymerizing a monomer having a reactive functional group, and then reacting a compound having both an active group and an amine oxide group capable of reacting with the functional group.

In the present invention, the term "water-soluble" means that 1 part by weight of an amine oxide group-containing resin and 99 parts by weight of deionized water are 6 parts by weight.
After heating and stirring at 0 ° C. for 2 hours and leaving it at room temperature for 1 day after cooling, the aqueous solution was uniform without forming a precipitate, and the transmittance of this aqueous solution at 655 nm in a 1 cm × 1 cm cell was 70%. This is what is described above. Hydrophilic monomer (A): In the water-soluble resin containing an amine oxide group used in the present invention, 30% by weight or more of the hydrophilic monomer (A) used for the polymerization is an amine oxide group-containing monomer. (A) is preferable, and the ratio of the amine oxide group-containing monomer (a) to the entire hydrophilic monomer (A) is more preferably 50% by weight or more.

Amine oxide group-containing monomer (a):
Examples of the amine oxide group-containing monomer of the component (a) include monomers represented by formulas (I) to (IV).

[0010]

Embedded image

(Wherein R ¹ represents a hydrogen atom or a methyl group;
R ² and R ³ are the same or different C ₁ may also be -C ₂₄ alkyl group, aryl group C ₆ -C _24, or an arylalkyl group of C ₇ -C _24, R ⁴ and R ⁵ are C alkyl group of ₁ -C _24, aryl group of C ₆ -C _24, or an arylalkyl group of C ₇ ~C _24, X is a divalent linking group, m is an integer of 0 to 1, n is 0 An integer of 0 to 4, p is an integer of 0 to 3, Y
Is

[0012]

Embedded image Other R ^{6 to} R ¹³ are a hydrogen atom or a C _{1 to} C ₂₄ alkyl group, a C _{6 to} C ₂₄ aryl group, or a C _{7 to} C ₂₄ arylalkyl group, and a and b are the same or different. Good one
And an integer of 10 to 10. The monomers represented by the general formula (I) include N, N-dimethylaminoethyl (meth) acrylate, N, N-diethylaminoethyl (meth) acrylate, N, N-dimethylaminopropyl (meth) acrylate, N, N-diethylaminopropyl (meth) acrylate, N, N-dimethylaminoethyl (meth) acrylamide, N, N-diethylaminoethyl (meth) acrylamide, N, N-
Dimethylaminopropyl (meth) acrylamide, N,
N-diethylaminopropyl (meth) acrylamide,
Amine oxides such as vinyl N, N-dimethylaminopropionate, p-dimethylaminomethylstyrene, p-dimethylaminoethylstyrene, p-diethylaminomethylstyrene and p-diethylaminoethylstyrene;
Alternatively, it contains a reactive group between an acid anhydride containing an unsaturated group such as maleic anhydride, itaconic anhydride and crotonic anhydride and an acid anhydride such as N, N-dimethyl-1,3-propanediamine and aniline. Reaction product with a product containing an epoxy group such as glycidyl methacrylate and an epoxy group such as N, N-dimethyl-1,3-propanediamine, and the like. Examples are amine oxides. Also, a product of an epoxy group-containing monomer such as glycidyl methacrylate and an amine oxide-containing material containing a group reactive with an epoxy group such as hydroxyethyl-N, N-dimethylamine oxide, 2-isocyanatoethyl ( Examples of the product include an isocyanate group-containing monomer such as meth) acrylate and an amine oxide-containing product containing a group reactive with an isocyanate group such as hydroxyethyl-N, N-dimethylamine oxide.

The monomers represented by the general formula (II) include 2-vinylpyridine, 3-vinylpyridine, 4-vinylpyridine, 2-methyl-5-vinylpyridine, and 3-methyl-5.
-Vinylpyridine, 4-methyl-5-vinylpyridine,
6-methyl-5-vinylpyridine, 2-methyl-4-vinylpyridine, 3-methyl-4-vinylpyridine, 2-
Alkyl, aryl, alkylaryl such as lauryl-5-vinylpyridine, 2-lauryl-4-vinylpyridine, 2- (t-butyl) -5-vinylpyridine, 2- (t-butyl) -4-vinylpyridine and the like Examples thereof include amine oxides such as adducts of groups.

The monomer represented by the general formula (III) includes 1-
Vinylimidazole, 2-methyl-1-vinylimidazole, 4-methyl-1-vinylimidazole, 5-methyl-1-vinylimidazole, 2-lauryl-1-vinylimidazole, 4- (t-butyl) -1-vinyl Examples thereof include amine oxides such as imidazole. The monomer represented by the general formula (IV) includes 4-vinylmorpholine, 2
-Methyl-4-vinylmorpholine, 4-allylmorpholine, 1-vinylpiperidine, 4-methyl-4-vinylpiperidine, 2-lauryl-1-vinylpiperazine, 2-
Examples thereof include amine oxides such as methylpiperazinoethyl methacrylate.

Among these, the monomers represented by the general formula (I) are most preferable, and R ² and R ³ of the general formula (I) are particularly preferable.
Is most preferably a C ₁ -C ₄ alkyl group. Nitrogen-containing precursor monomer (b): Examples of the nitrogen-containing monomer before being oxidized include monomers represented by the following formulas (V) to (VIII).

[0016]

Embedded image

(Wherein R1 to R10, a, b, m, n,
The definitions of p, X, and Y are the same as those in the formulas (I) to (IV). ) Other hydrophilic monomers (c): Examples of such hydrophilic monomers include nonionic, anionic, cationic, or amphoteric monomers having anionic and cationic zwitterions in the same molecule. .

Among such monomers, specific examples of nonionic monomers include hydroxyethyl (meth) acrylate, polyethylene glycol (meth) acrylate, and methoxy poly (ethylene glycol / propylene glycol) mono (meth) acrylate. A monomer derived from (meth) acrylic acid or (meth) acrylamide such as polyethylene glycol di (meth) acrylate, N-polyalkyleneoxy (meth) acrylamide and an alkylene oxide having 2 to 4 carbon atoms, and ( (Meth) acrylonitrile, N-cyclohexylmaleimide, N-
Examples thereof include hydrophilic monomers such as phenylmaleimide, N-vinylpyrrolidone, N- (meth) acryloylmorpholine, and acrylamide.

Specific examples of the anionic monomer include:
Unsaturated carboxylic acid monomers such as (meth) acrylic acid, maleic acid, maleic anhydride, itaconic acid, fumaric acid, crotonic acid; unsaturated polybasic anhydrides (for example, succinic anhydride,
Half ester of phthalic anhydride or the like and a hydroxy group-containing (meth) acrylate (for example, hydroxyethyl (meth) acrylate or the like); a monomer having a sulfonic acid group such as styrenesulfonic acid or sulfoethyl (meth) acrylate; Monomers having a phosphate group such as phosphooxyethyl (meth) acrylate are exemplified.

These anionic unsaturated monomers can be used as they are, partially neutralized or completely neutralized, or they can be used as they are for copolymerization and then partially neutralized or completely neutralized. You can also sum up. Examples of the base used for neutralization include alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, aqueous ammonia, and amine compounds such as mono, di, triethanolamine and trimethylamine.

Specific examples of the cationic monomer include:
N, N-dimethylaminoethyl (meth) acrylate,
N, N-diethylaminoethyl (meth) acrylate,
N, N-dimethylaminopropyl (meth) acrylate, N, N-diethylaminopropyl (meth) acrylate, N, N-dimethylaminoethyl (meth) acrylamide, N, N-diethylaminoethyl (meth) acrylamide, N, N- Dimethylaminopropyl (meth) acrylamide, N, N-diethylaminopropyl (meth) acrylamide, p-dimethylaminomethylstyrene, p-dimethylaminoethylstyrene, p-diethylaminomethylstyrene, p-diethylaminoethylstyrene, etc. are used as cationizing agents. For example, alkyl halides such as methyl chloride, methyl bromide, and methyl iodide; dialkyl sulfates such as dimethyl sulfate; N- (3-chloro-2-hydroxypropyl) -N, N, N-trimethylammonium chloride; The third Epichlorohydrin adducts of amines mineral, hydrochloric, hydrobromic, sulfuric, inorganic salts such as phosphoric acid, formic acid, acetic acid, cationic monomer which is cationized with a carboxylic acid such as propionic acid.

As specific examples of the amphoteric unsaturated monomer, the above-mentioned cationic monomer can be used as a zwitterionic monomer by using a modifying agent such as sodium or potassium haloacetate as a modifying agent. Can be used. Hydrophobic monomer (B): As the hydrophobic monomer (B), C
₁ -C ₂₄ alcohol (meth) acrylic acid alkyl ester, styrene, p- methyl styrene, p- chlorostyrene, vinyl methyl ether, vinyl cyclohexyl ether, vinyl acetate, diethyl maleate, hydrophobic vinyl such as dibutyl maleate Examples include monomers, glycidyl (meth) acrylates, fluoroalkyl esters of (meth) acrylic acid, and unsaturated group-containing macromonomers such as radically polymerizable unsaturated group-containing silicon macromonomers.

Examples of the above (meth) acrylates of alcohols having 1 to 24 carbon atoms include (meth)
Methyl acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, secondary butyl (meth) acrylate,
Tert-butyl (meth) acrylate, pentyl (meth) acrylate, secondary pentyl (meth) acrylate, 1-ethylpropyl (meth) acrylate, 2-methylbutyl (meth) acrylate, isopentyl (meth) acrylate, Tert-pentyl (meth) acrylate, 3-methylbutyl (meth) acrylate, neopentyl (meth) acrylate, hexyl (meth) acrylate,
2-methylpentyl (meth) acrylate, 4-methylpentyl (meth) acrylate, 2-ethylbutyl (meth) acrylate, cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, heptyl (meth) acrylate, 2-heptyl (meth) acrylate, 3-heptyl (meth) acrylate, octyl (meth) acrylate,
2-octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isooctyl (meth) acrylate, nonyl (meth) acrylate, 3,3,5-trimethylhexyl (meth) acrylate, (meth) acryl Decyl acid, undecyl (meth) acrylate, lauryl (meth) acrylate, cetyl (meth) acrylate, (meth)
Stearyl acrylate, eicosyl (meth) acrylate, docosyl (meth) acrylate, tetracosyl (meth) acrylate, methylcyclohexyl (meth) acrylate, isobornyl (meth) acrylate, norbornyl (meth) acrylate, (meth) Examples include benzyl acrylate and phenethyl (meth) acrylate.

Among them, (meth) acrylates of C ₁ -C ₂₄ alcohols, especially C ₁ -C ₁₈
(Meth) acrylic acid esters of alcohols are preferred. (A) The polymerization ratio of the component (B): The preferred amount of the hydrophobic monomer used as the component (B) is the degree of hydrophobicity of the component (B), the use of the obtained amine oxide group-containing water-soluble resin. Depends on usage. Generally, it is not more than 85% by weight of the whole monomers to be subjected to polymerization, and is within a range that does not impair the water solubility of the resin after polymerization. Hair cosmetics are broadly divided into sets and conditioning.

When used as a setting resin, (A)
It is preferable that the component is a copolymer of 15 to 90% by weight and the component (B) is 85 to 10% by weight. (A) Component is 15
When the amount is less than the weight percentage, the smoothness and transparency of the copolymer film are deteriorated, and the copolymer film becomes hardly soluble in water, and it may be difficult to wash and remove the hair during washing. If the component (A) exceeds 90% by weight, the setting force may be insufficient.

Hair cosmetics for setting are in the form of spray, mousse, gel and the like. For example, when used as a spray resin, the component (A) preferably has a content of 15 to 90%.
% By weight, 85 to 10% by weight of component (B), more preferably 30 to 80% by weight of component (A), and 70 to 80% by weight of component (B).
20% by weight. When used as a mousse resin,
Since the proportion of water used as a solvent is large, the hydrophilicity is required to be relatively high.
The content of the component (A) is from 40 to 80% by weight, and the content of the component (B) is from 60 to 20% by weight.

When used as a gel resin, the proportion of water is high similarly to mousse, so that appropriate hydrophilicity is required, and from the viewpoint of affinity with the gel base, the component (A) preferably has a content of 40%. ~ 90% by weight, component (B) is 60%
-10% by weight, more preferably 50-80% by weight of the component (A).
% By weight, and 50 to 20% by weight of the component (B). on the other hand,
When used as a conditioning resin, the hydrophilicity is required to be high for smooth feel of hair and easy removal by washing. Preferably, component (A) is 3%.
0 to 100% by weight, component (B) is 0 to 70% by weight, more preferably component (A) is 50 to 100% by weight, and component (B) is 0 to 50% by weight.

Polymerization method: When actually producing the amine oxide group-containing water-soluble resin of the present invention, the nitrogen-containing precursor monomer represented by the above formulas (V) to (VIII) is oxidized to obtain A method of polymerizing or copolymerizing an amine oxide group-containing monomer, and a method of homogenizing or copolymerizing the nitrogen-containing precursor monomer represented by the formulas (V) to (VIII). Method of Oxidation A method of polymerizing a monomer having a reactive group and reacting a substance having both an active group capable of reacting with the functional group and an amine oxide group can be employed. Among them, the method is preferable.

The amine oxide group-containing resin is prepared by subjecting the above monomer component to solution polymerization, usually in the presence of a radical polymerization initiator.
It is obtained by polymerizing by a known method such as bulk polymerization or suspension polymerization. In particular, it can be suitably obtained by solution polymerization. As the polymerization solvent, an organic solvent such as acetone, methyl ethyl ketone, methyl isobutyl ketone, methanol, ethanol, propanol, isopropanol, butanol, isobutanol, secondary butanol, ethyl acetate, propyl acetate, and butyl acetate may be used alone or in combination of two or more. Used as a mixture.

As the radical polymerization initiator, 2,2'-
Azobisisobutyronitrile (AIBN), 2,2'-
Azobis (2,4-dimethylvaleronitrile), 2,
2'-azobis (4-methoxy-2,4-dimethylvaleronitrile), dimethyl-2,2'-azobisisobutyrate, 2,2'-azobis (2-methylbutyronitrile), 1,1 ' Azo compounds such as -azobis (1-cyclohexanecarbonitrile), benzoyl peroxide,
Dicumyl peroxide, di-t-butyl peroxide,
A peroxide such as lauroyl peroxide is used.
These polymerization initiators are usually used in an amount of 0.01 to 5% by weight based on the components (A) and (B). The polymerization is carried out usually at 30 ° C. to 120 ° C., preferably at 40 ° C. to 100 ° C. for 1 to 20 hours under an atmosphere of an inert gas such as nitrogen or argon.

Oxidation: For example, when the amine oxide group-containing water-soluble resin used in the present invention is produced by the above method, an oxidizing agent is added to a precursor polymer solution obtained by polymerizing a monomer component. In addition, amine oxide group-containing water-soluble resin can be obtained by oxidizing in a range of 20 ° C to 100 ° C for 0.1 to 100 hours, preferably 1 to 50 hours.

As the oxidizing agent, an oxidizing agent such as peroxide or ozone is used. The peroxide includes hydrogen peroxide, ammonium persulfate, sodium persulfate, peracetic acid, metachloroperbenzoic acid, benzoyl peroxide, t-butyl hydroperoxide, and the like.In general, hydrogen peroxide is usually used. Is used in the form of an aqueous solution. The oxidizing agent is used in an amount of 0.2 to 3 molar equivalents, more preferably 0.5 to 2 molar equivalents, based on the oxidizable functional group contained in the precursor polymer. Is more preferred. The obtained resin solution can be used for hair cosmetics without treating the remaining peroxide, but can be used after being treated by a known method. Specific examples include a reducing agent addition treatment, an ion exchange treatment, an activated carbon treatment, and a treatment with a metal catalyst.

The obtained resin solution can be used as it is, but if necessary, an amine oxide group-containing resin can be isolated and used by a known method such as reprecipitation or solvent distillation. The isolated amine oxide group-containing resin can be further purified, if necessary, by reprecipitation, solvent washing, membrane separation, adsorption treatment, or the like. Obtained in this way,
The resin of the present invention has a weight average molecular weight of 5,000 to 1,000.
0000, preferably 10,000 to 500,000
0, more preferably 20,000 to 300,000. In general, resins used for hair cosmetics are preferably those having a relatively small molecular weight for setting and those having relatively large molecular weight for conditioning.
The same applies to the resin of the present invention. The weight average molecular weight is 5,000 to 300,000 for the set, and 20,000 to 1,000,000 for the conditioning.
Are preferred.

[0034]

BEST MODE FOR CARRYING OUT THE INVENTION The water-soluble resin containing an amine oxide group used in the present invention is added as a resin for hair cosmetics to hair cosmetics such as shampoos, rinses, treatments, setting agents, and permanent wave liquids. use. At this time, you may use together with the well-known polymer conventionally used. Hair cosmetics to be used are liquid,
It may be in any form such as cream, emulsion, gel, mousse. The amount of the amine oxide group-containing water-soluble resin varies depending on the form and purpose of the hair cosmetic, or the type and amount of the polymer used in combination. It is preferable to add at a ratio of weight%.

1) When used for a set product This set product is an aerosol hair spray, a pump type hair spray, a foam hair spray, a hair mist,
It includes well-known hair styling compositions using water and / or alcohols such as ethanol and isopropanol as solvents, such as set lotions, hair stylings, hair creams, and hair oils. The amine oxide group-containing resin is used alone or in combination with a conventional cationic, anionic, nonionic and amphoteric known setting polymer.

For example, when used as a hair cosmetic (mousse) which can be spouted in a foam state, the composition is 0.01 to 10% by weight of an amine oxide group-containing water-soluble resin, 0 to 15% by weight of a known setting polymer, Nonionic surfactant 0.
1 to 5% by weight, 3 to 25% by weight of liquefied gas and 60% by weight of water-soluble solvent mainly composed of water to the remainder. (However, water is contained in hair cosmetics in an amount of 60% by weight or more).

When used as a gel, the composition is 0.01 to 10% by weight of a water-soluble resin containing an amine oxide group, 0 to 15% by weight of a known setting polymer, 0.1 to 3% by weight of a gel base, and 72% of water. % By weight to the balance. When used as a hair spray, the composition is 0.01 to 10% by weight of an amine oxide group-containing resin, 0 to 15% by weight of a known setting polymer, 30 to 80% by weight of a solvent,
７０70% by weight. Examples of known setting polymers that can be used in combination include cationic polymers such as ethers of hydroxycellulose and glycidyltrimethylammonium chloride (trade name: LEOGARD G (manufactured by Lion), trade names: polymer JR-30M-125 and
400 (manufactured by Union Carbide Co.)), 4 of vinylpyrrolidone-dimethylaminoethyl methacrylate copolymer
Grade (trade name: GAFQUAT 734 and 755)
(Manufactured by GAF)), dimethyl diallyl ammonium chloride polymer (trade name: MERQUAT 100 (manufactured by Merck)), dimethyl diallyl ammonium chloride acryloamide copolymer (trade name: MERQUAT)
550 (manufactured by Merck)).

Examples of the anionic polymer include, for example, a copolymer of (meth) acrylic acid and an alkyl methacrylate (trade name: Diahold (manufactured by Mitsubishi Chemical Corporation), trade name: plus size (manufactured by Yoyo Chemical Co., Ltd.) )), Monoalkyl maleate and methyl vinyl ether copolymer (trade name: GANTREZ (manufactured by ISP)).

Examples of the nonionic polymer include a polyvinylpyrrolidone polymer (trade name: PVP (manufactured by ISP)) and vinylpyrrolidone and a vinyl acetate copolymer (trade name: LUVISKOL (manufactured by BASF)). Examples of the amphoteric polymer include a methacrylic acid ester copolymer (trade name: Yuka Former-AM-75W (manufactured by Mitsubishi Chemical Corporation)).

Examples of nonionic surfactants that can be used in mousse include sorbitan fatty acid ester, glycerin fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyethylene glycol fatty acid ester, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, Polyoxyethylene castor oil, polyoxyethylene hydrogenated castor oil, fatty acid alkanolamide, and the like.

Examples of the propellant usable for spraying or mousse include liquefied petroleum gas, liquefied gas such as dimethyl ether and halogenated hydrocarbon, and compressed gas such as air, carbon dioxide gas and nitrogen gas. 2) When used for products with conditioning function Hair cosmetics for imparting conditioning function include hair cosmetics whose solvent is water and / or alcohols such as ethanol and isopropanol, such as shampoo, rinse and permanent liquid, or There are hair cosmetics, such as hair treatments, in which the solvent is water and / or alcohols such as ethanol and isopropanol, or alcohols and / or hydrocarbons having a boiling point of 50 ° C to 300 ° C. Amine oxide group-containing resin alone, as in the above-mentioned set products, or conventional cationic, anionic,
It is used in combination with a known nonionic and amphoteric conditioning polymer.

For example, when used as a shampoo,
An amine oxide group-containing water-soluble resin is added to a known anionic, amphoteric or nonionic surfactant substrate. As an example of the surfactant base material, as the anionic surfactant, N-coconoyl-N-methyl-β-alanine sodium, N-myristoyl-N-methyl-β-
N-fatty acid acyl-N-methyl-β-alanine salts such as sodium alanine and the like are used as amphoteric surfactant bases. Cocoaside propyl betaine, dimethyl lauryl betaine, bis (2-hydroxyethyl) lauryl betaine, cyclohexyl lauryl Amine oxide, dimethyl lauryl amine oxide, bis (2-hydroxyethyl) lauryl amine oxide and the like, and nonionic surfactant base materials include stearic acid diethanolamide, coconut oil fatty acid diethanolamide, sorbitan sesquioleate, polyoxy And ethylene stearyl ether.

When used as a rinse, a water-soluble resin containing an amine oxide group is added to a known cationic surfactant. Examples of the cationic surfactant base include stearyltrimethylammonium chloride, distearyldimethylammonium chloride, and stearyldimethylbenzylammonium chloride. When used as a permanent liquid, a water-soluble resin containing an amine oxide group is added to a known oxidizing agent such as bromates and perboric acids, and a reducing agent such as thioglycolic acid and salts thereof and cysteine.

When used as a hair treatment, it may be used in combination with or in place of a known cationic surfactant base material and / or a cationized polymer such as a cationic polypeptide, a cationic cellulose, or a cationic polysiloxane. A water-soluble resin containing an amine oxide group is added and used. As the cationic surfactant substrate, those exemplified as usable for rinsing, for example, can be used for hair treatment.

Optional Ingredients: In each case of the set product and the product with a conditioning function, other optional components are blended, if necessary, in addition to the above-mentioned various components, as long as the effects of the present invention are not affected. May be. Examples of the optional components include liquid paraffin, petrolatum, solid paraffin, squalane, hydrocarbons such as olefin oligomers, ethanol, lauryl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol, myristyl alcohol, oleyl alcohol, cetostearyl alcohol and the like. Chain alcohols; alcohols such as branched alcohols such as monostearyl glycerin ether, 2-decyltetradecinol, lanolin alcohol, cholesterol, phytosterol, hexyldecanol, isostearyl alcohol, and octyldodecanol; lauric acid, myristic acid, and palmitin Acid, stearic acid, behenic (behenyl) acid, oleic acid, 1,2-
Hydroxystearic acid, undecylenic acid, tallic acid,
Lanolin fatty acids, isostearic acid, linoleic acid, linoleic acid, γ-linolenic acid, higher fatty acids such as eicosapentaenoic acid and derivatives thereof,

Carrageenan, pectin, agar, quince seed (quince), alge colloid (cassow extract), starch (rice, corn, potato,
Plant-based polymers such as wheat) and glycyrrhizic acid; microbial polymers such as xanthan gum, dextran and pullulan; natural water-soluble polymers such as animal-based polymers such as collagen and gelatin; methylcellulose; ethylcellulose;
Cellulose polymers such as methylhydroxypropylcellulose, hydroxyethylcellulose, cellulose sodium sulfate, hydroxypropylcellulose, sodium carboxymethylcellulose (CMC), crystalline cellulose and cellulose powder; alginic acid polymers such as sodium alginate and propylene glycol alginate; Semi-synthetic water-soluble polymer,

Vinyl polymers such as polyvinyl alcohol, polyvinyl methyl ether, polyvinyl pyrrolidone and carboxyvinyl polymer (Carbopol); polyethylene glycol 20,000, 4,000,000, 6
Polyoxyethylene polymers such as 00000; synthetic water-soluble polymers such as polyethyleneimine, bentonite,
Inorganic water-soluble polymers such as AlMg silicate (Vegum), Rabonite, hectorite, and silicic acid, volatile silicone oils, silicone resins, silicone gums, silicones such as alkyl-modified silicones, N-lauryl-L-glutamic acid Monosodium, N-coconut oil fatty acid-L-glutamate monotriethanolamine, N-acyl myristylate-L-glutamate monosodium, N-mixed fatty acid acyl-L-glutamate monosodium, etc.
-Fatty acid acyl-L-glutamate,

N-fatty acids such as sodium laurate methyltaurine, coconut oil fatty acid sodium methyltaurine, etc.
Salts of N-fatty acid sarcosine condensates such as N-methyltaurine salt, sodium lauroyl sarcosine, cocoyl sarcosine sodium, acyl sarcosine sodium, acyl glutamate, acyl-β-alanine sodium,
Surfactants such as acyl taurate, lauryl sulfate, betaine lauryl dimethylaminoacetate, alkyl trimethyl ammonium chloride, polyoxyethylene hydrogenated castor oil,

1-hydroxyethane-1,1-diphosphonic acid, 1-hydroxyethane-1,1-diphosphonic acid tetrasodium salt, disodium edetate, trisodium edetate, tetrasodium edetate, sodium citrate, polyphosphoric acid Sequestering agents such as sodium silicate, sodium metaphosphate, gluconic acid, 3- (4'-methylbenzylidene) -d, 1-camphor, 3-benzylidene-d, 1-camphor, urocanic acid, urocanic acid ethyl ester, 2-phenyl-5-methylbenzoxazole, 2,2'-hydroxy-5-methylphenylbenzotriazole, 2- (2'-hydroxy-5'-t-
Octylphenyl) benzotriazole, 2- (2'-
Hydroxy-5'-methylphenylbenzotriazole, dibenzalazine, dianisoylmethane, 4-methoxy-4'-t-butyldibenzoylmethane, 5- (3,
Various ultraviolet absorbers such as 3-dimethyl-2-norbornylidene) -3-pentan-2-one, benzoic acid, anthranilic acid, salicylic acid, cinnamic acid, and benzophenone;

Emulsifiers such as glyceryl monostearate, sorbitan monopalmitate, polyoxyethylene cetyl ether, polyoxyethylene sorbitan monolaurate, (poly) ethylene glycol, (poly) propylene glycol, glycerin, 1,3-butylene glycol , Maltitol, sorbitol, chondroitin sulfate, hyaluronic acid, atelocollagen, cholesteryl-1,2-hydroxystearate, sodium lactate,
Humectants such as bile salts, dl-pyrrolidone carboxylate, short-chain soluble collagen, antibacterial agents such as hinokitiol, hexachlorophene, benzalkonium chloride, trichlorocarbanilide and picionol; vasodilators such as carpronium chloride; menthol Stimulants such as benzyl nicotinate, etc., vitamin A, B,
Bactericidal preservatives such as vitamins such as C, D, and E, chlorhexidine gluconate, isopropylmethylphenol, and paraoxybenzoate;

Protein hydrolyzate, amino acid, plant extract, chelating agent such as EDTA-Na, succinic acid,
PH adjusters such as sodium succinate and triethanolamine, foaming agents, foaming agents, foam stabilizers, in the case of aerosol products, liquefied petroleum gas, propellants such as dimethyl ether, metal ion scavengers, fungicides, fungicides , An emulsifier, a conditioning agent, a thickener, an antioxidant, a solubilizer, a rosin, a hydrotrope, a hair restorer, a crude drug, a pigment, a fragrance, and the like.

[0052]

EXAMPLES Hereinafter, the present invention will be described more specifically with reference to Examples, but the present invention is not limited to these Examples. Production Example 1 70 parts by weight of N, N-dimethylaminoethyl methacrylate and N-vinylpyrrolidone 20 were placed in a reactor equipped with a reflux condenser, a dropping funnel, a thermometer, a nitrogen gas inlet tube and a stirrer.
Parts by weight, 10 parts by weight of t-butyl methacrylate, and 150 parts by weight of absolute ethanol, 0.6 part by weight of 2,2′-azobisisobutyronitrile was charged, and the mixture was reacted at 80 ° C. for 8 hours under a nitrogen atmosphere. Cooled to 60 ° C. next,
A 31% aqueous solution of N, N-dimethylaminoethyl methacrylate and an equimolar amount of hydrogen peroxide was dropped into the polymerization solution in a dropping funnel over 1 hour, and the dimethylamino group was oxidized by continuing stirring for 20 hours. . Completion of the oxidation reaction was confirmed by measuring the amine value of the reaction solution. The obtained polymer is designated as "P-1". In addition, the obtained polymer weight average molecular weight was 110,000. In addition, N-O absorption was recognized from the infrared absorption spectrum,
Generation of an amine oxide group was confirmed.

Production Example 2 30 parts by weight of N, N-dimethylaminoethyl methacrylate, 70 parts by weight of stearyl methacrylate, and 150 parts by weight of absolute ethanol were placed in a reactor similar to that of Production Example 1, and 2,2'-azobisiso- After charging 0.6 parts by weight of butyronitrile and reacting at 80 ° C. for 8 hours in a nitrogen atmosphere,
Cooled to ° C.

Next, an equimolar 31% aqueous solution of hydrogen peroxide of N, N-dimethylaminoethyl methacrylate was added dropwise over 1 hour, and the dimethylamino group was oxidized by continuing stirring for 20 hours. Completion of the oxidation reaction was confirmed by measuring the amine value of the reaction solution. The obtained polymer is designated as "P-2". The weight average molecular weight of the obtained polymer was 100,000. In addition, N-O absorption was recognized from the infrared absorption spectrum, and formation of an amine oxide group was confirmed.

Production Example 3 In the same reactor as in Production Example 1, 40 parts by weight of N, N-dimethylaminopropyl methacrylamide, 30 parts by weight of methyl methacrylate, 25 parts by weight of t-butyl methacrylate,
5 parts by weight of a polysiloxane FM0721, 0.6 parts by weight of 2,2-azobisisobutyronitrile, and 150 parts by weight of absolute ethanol were added, and the mixture was heated and refluxed at 80 ° C. under a nitrogen atmosphere, and further polymerized for 10 hours.

Next, a 31% aqueous solution of 1.2% by mole of hydrogen peroxide of N, N-dimethylaminopropyl methacrylamide was dropped into the polymerization solution in a dropping funnel in 1 hour, and stirring was continued for 10 hours. The dimethylamino group was oxidized by the method described above. The end of the oxidation reaction is
It was confirmed by measuring the amine value of the reaction solution. The obtained polymer is designated as "P-3". The weight average molecular weight of the obtained polymer was 80,000. In addition, N-O absorption was recognized from the infrared absorption spectrum, and formation of an amine oxide group was confirmed.

Production Example 4 50 parts by weight of N, N-dimethylaminoethyl methacrylate, 50 parts by weight of t-butyl methacrylate, and 150 parts by weight of absolute ethanol were placed in a reactor similar to that of Production Example 1, and 2,2'-azo 0.6 parts by weight of bisisobutyronitrile was charged, and heated to 80 ° C. in a nitrogen atmosphere for 40 minutes.
After reacting at 80 ° C. for 8 hours, it was cooled to 60 ° C.

Next, an equimolar 31% aqueous solution of hydrogen peroxide of N, N-dimethylaminoethyl methacrylate was added dropwise over one hour, and the dimethylamino group was oxidized by continuing stirring for another 20 hours. Completion of the oxidation reaction was confirmed by measuring the amine value of the reaction solution.
The obtained polymer is designated as "P-4". The weight average molecular weight of the obtained polymer was 100,000. In addition, N-O absorption was recognized from the infrared absorption spectrum, and formation of an amine oxide group was confirmed.

Preparation Example 5 In a reactor similar to that of Preparation Example 1, 100 parts by weight of N, N-dimethylaminoethyl methacrylate and 1 part of anhydrous ethanol were added.
50 parts by weight, 0.1 part by weight of 2,2'-azobisisobutyronitrile was charged, and 8 parts in 40 minutes in a nitrogen atmosphere.
The temperature was raised to 0 ° C., the reaction was performed at 80 ° C. for 8 hours, and then cooled to 60 ° C.

Next, a 31% aqueous solution of hydrogen peroxide of 1.2 times the molar amount of N, N-dimethylaminoethyl methacrylate was added dropwise over 1 hour, and the dimethylamino group was oxidized by continuing stirring for 20 hours. Was. Completion of the oxidation reaction was confirmed by measuring the amine value of the reaction solution. The obtained polymer is designated as "P-5". The weight average molecular weight of the obtained polymer was 200,000. In addition, N-O absorption was recognized from the infrared absorption spectrum,
Generation of an amine oxide group was confirmed.

Production Example 6 In a reactor similar to that of Production Example 1, 80 parts by weight of N, N-dimethylaminoethyl methacrylate and butyl methacrylate 2 were added.
0 parts by weight and 150 parts by weight of absolute ethanol,
After charging 0.6 parts by weight of 2,2'-azobisisobutyronitrile and reacting at 80 ° C. for 8 hours under a nitrogen atmosphere,
And cooled.

Next, a 0.5% molar aqueous solution of hydrogen peroxide of 31% of N, N-dimethylaminoethyl methacrylate was added dropwise over 1 hour, and the dimethylamino group was oxidized by continuing stirring for 20 hours. Was. Completion of the oxidation reaction was confirmed by measuring the amine value of the reaction solution. The obtained polymer is designated as "P-6". The weight average molecular weight of the obtained polymer was 110,000. In addition, N-O absorption was recognized from the infrared absorption spectrum,
Generation of an amine oxide group was confirmed.

Production Example 7 45 parts by weight of N, N-dimethylaminoethyl methacrylate, 35 parts by weight of octyl methacrylate, 20 parts by weight of butyl acrylate, and 150 parts by weight of anhydrous ethanol were placed in the same reactor as in Production Example 1, and 0.6 part by weight of 2'-azobisisobutyronitrile was charged, and under nitrogen substitution,
After reacting at 80 ° C. for 8 hours, it was cooled to 60 ° C.

Next, a 31% aqueous solution of hydrogen peroxide of 0.5 times the molar amount of N, N-dimethylaminoethyl methacrylate was added dropwise over 1 hour, and the dimethylamino group was oxidized by continuing stirring for 20 hours. Was. next,
A potassium hydroxide-neutralized product of monochloroacetic acid prepared in advance was added dropwise to the flask with a dropping funnel in a 0.5-fold molar amount of N, N-dimethylaminoethyl methacrylate. Further, an amphoteric reaction was carried out at 80 ° C. for 20 hours in a nitrogen atmosphere. Completion of the reaction was confirmed by measuring an amine value of the reaction solution. The obtained polymer is designated as "P-7". The weight average molecular weight of the obtained polymer was 110,00.
It was 0. In addition, N-O absorption was recognized from the infrared absorption spectrum, and formation of an amine oxide group was confirmed.

Production Example 8 80 parts by weight of N, N-dimethylaminoethyl methacrylate, 20 parts by weight of stearyl acrylate, and 150 parts by weight of absolute ethanol were placed in a reactor similar to that of Production Example 1.
1.0 part by weight of 2,2'-azobisisobutyronitrile was charged, and reacted at 80 ° C. for 8 hours under a nitrogen atmosphere.
And cooled. Next, a 31% aqueous solution of hydrogen peroxide, 1.5 times the molar amount of N, N-dimethylaminoethyl methacrylate, was added dropwise over 1 hour, and the dimethylamino group was oxidized by continuing stirring for 20 hours. Completion of the oxidation reaction was confirmed by measuring the amine value of the reaction solution. The obtained polymer is designated as "P-8". The weight average molecular weight of the obtained polymer was 50,000. Also,
From the infrared absorption spectrum, absorption of NO was recognized, and the formation of an amine oxide group was confirmed.

Production Example 9 A reactor similar to that of Production Example 1 was charged with 5 parts by weight of N, N-dimethylaminoethyl methacrylate, 80 parts by weight of stearyl methacrylate, 15 parts by weight of ethyl methacrylate, and 150 parts by weight of butanol. '-Azobisisobutyronitrile, 0.6 parts by weight, and under a nitrogen atmosphere,
After reacting at 80 ° C. for 8 hours, it was cooled to 60 ° C. Next, N,
A dimethylamino group was oxidized by dropwise adding a 31% aqueous solution of hydrogen peroxide in a 1.0-fold molar amount of N-dimethylaminoethyl methacrylate over 1 hour and continuing stirring for 20 hours. Completion of the oxidation reaction was confirmed by measuring the amine value of the reaction solution. The obtained polymer is designated as "P-9". The weight average molecular weight of the obtained polymer was 150,000. In addition, N-O absorption was recognized from the infrared absorption spectrum, and formation of an amine oxide group was confirmed.

Production Example 10 20 parts by weight of N, N-dimethylaminoethyl methacrylate, 30 parts by weight of lauryl methacrylate, fluoroalkyl methacrylate (trade name “Light Ester FM-108”, Kyoeisha Chemical Co., Ltd.) 50 parts by weight) and 150 parts by weight of butanol,
After charging 0.6 parts by weight of 2,2'-azobisisobutyronitrile and reacting at 80 ° C. for 8 hours under a nitrogen atmosphere,
And cooled.

Next, a dimethylamino group was oxidized by dropwise adding a 31% aqueous solution of hydrogen peroxide in a 1.2-fold molar amount of N, N-dimethylaminoethyl methacrylate over 1 hour and continuing stirring for 20 hours. Was. Completion of the oxidation reaction was confirmed by measuring the amine value of the reaction solution. The obtained polymer is set to "P-10". The weight average molecular weight of the obtained polymer was 100,000. In addition, N-O absorption was recognized from the infrared absorption spectrum,
Generation of an amine oxide group was confirmed.

"P-1" obtained in Production Examples 1 to 10
The water solubility of "P-10" was measured, and the results are shown in Table 1. The measuring method and evaluation criteria are as follows. <Water solubility> 1 part by weight of polymer and 99 parts by weight of deionized water were heated and stirred at 60 ° C. for 2 hours. After cooling, the aqueous solution was allowed to stand for 1 day. 100%: ○, 30-70%: Δ, 0
３０30%: x

[0070]

[Table 1]

Example 1 The following shampoo composition was prepared. (% By weight) Sodium polyoxyethylene lauryl sulfate (3EO adduct) 16% Lauroyl diethanolamide 2% "P-1" 1.5% Fragrance 0.2% Preservative 0.1% Pigment trace amount Pure water Balance ─── ──────────────────────────────── 100%

When this composition was used as a shampoo, the hair after shampooing could be easily combed,
The hair after drying had excellent gloss and luster and could be easily combed with a smooth feel. Further, even if shampoo was repeated, there was no adverse effect such as stickiness. In addition, the same results as described above were obtained with the compositions using the polymers “P-4”, “P-5”, “P-6”, and “P-8”.

Comparative Example 1 When the same composition as in Example 1 was used as a shampoo using “P-9” and “P-10”, it was difficult to dissolve in water. There was no smooth feel and combing was poor.

Experimental Example 2 The following rinse composition was prepared. (Wt%) Stearyltrimethylammonium chloride 1.5% Cetanol 2% “P-2” 1.5% Fragrance 0.2% Pure water Balance ────────────────── ───────────────── 100%

When this composition was used for rinsing, the hair after rinsing could be easily combed, and the hair after drying had excellent gloss and luster, and was easily combed with a smooth feel. Was able to. Further, even if rinsing was repeated, there was no adverse effect such as stickiness. In addition, "P-
1 "" P-3 "" P-4 "" P-5 "" P-6 "" P-
The same results as described above were obtained with the composition using the polymer No. 8 ".

Comparative Example 2 When the same composition as in Example 2 was used as a rinse using “P-9” and “P-10”, the hair after drying was difficult to dissolve in water. There is no smooth feel,
Combing was also bad.

Example 3 A hair spray composition was prepared by placing the following diluted stock solution in a spray can and filling with liquefied petroleum gas. Dilute stock solution (wt%) "P-2" 4% Absolute ethanol 46% ───────────────────────────────── ── 50% liquefied petroleum gas (3 kg / cm2 G, 20 ° C) 50%

When this composition was spray-applied to hair and used, it gave an excellent set holding power to hair,
In addition, it gave the hair excellent gloss and luster and a smooth feel. Also, "P-1", "P-3", "P-4", "P-
The same results as described above were obtained with the compositions using the polymers No. 6, "P-7" and "P-8".

Comparative Example 3 The same composition as in Example 3 was spray-applied and used using “P-9” and “P-10”. Had no gloss, luster, or smooth feel.

Example 4 In the same manner as in Example 3, a foam aerosol composition was prepared. Diluted stock solution (% by weight) "P-3" 2% Carboxybetaine-type amphoteric polymer (trade name "Yukaformer AM-75R 205S" manufactured by Mitsubishi Chemical Corporation) 2% Polyoxyethylene cetyl ether (10EO adduct) 0.3% Poly Oxyethylene cetyl ether (2EO adduct) 0.1% Pure water balance (83.6%) ──────────────────────────── ８８ 88% Liquefied petroleum gas (3kg / cm2 G, 20 ° C) 12%

When this composition was sprayed onto hair and used, excellent results similar to those of Example 3 were obtained.
In addition, "P-1", "P-2", "P-4", "P-6", "P
The same results as above were obtained with the compositions using the polymers of "-7" and "P-8".

Comparative Example 4 The same composition as in Example 4 was spray-coated using “P-9” and “P-10”, and the set retention was evaluated because of poor solubility in water. No, and the hair did not give a gloss, luster or smooth feel.

Example 5 The following set lotion composition was prepared. (% By weight) "P-4" 3% Pure water 60% Absolute ethanol Balance (37%) ──────────────────────────── ─────── 100%

When this composition was applied to hair and used,
The same excellent results as in Example 4 were obtained. In addition, "P-
1, P-2, P-3, P-6, P-7, P-
The same results as described above were obtained with the composition using the polymer No. 8 ".

Comparative Example 5 When the same composition as in Example 5 was used as a set lotion using "P-9" and "P-10", the set holding power was weak for hair and the hair was glossy Glossy, did not give a smooth feel.

Example 6 The following gel composition was prepared. (% By weight) “P-4” 2% gel base (trade name “Carbopol 940” BF 0.5% manufactured by Goodrich Chemical) Pure water Balance (97.5%) ─────── ──────────────────────────── 100%

When this composition was used as a gel on hair, it gave excellent set holding power to the hair, and also gave the hair excellent gloss and luster and a smooth feel. When the application and use of the gel composition and the washing of the hair were repeated, there was no adverse effect such as stickiness and discomfort due to accumulation. "P-1", "P-2", "P-3"
The same results as described above were obtained with the compositions using the polymers of "P-6", "P-7" and "P-8".

Comparative Example 6 When a composition similar to that of Example 6 was used as a gel using “P-9” and “P-10”, the set holding power could not be evaluated due to poor solubility in water. , And the hair is shiny,
Glossy, did not give a smooth feel.

Comparative Example 7 90 parts by weight of N, N-dimethylaminoethyl methacrylate, 70 parts by weight of butyl methacrylate, lauryl were placed in a five-necked flask equipped with a reflux condenser, a dropping funnel, a thermometer, a nitrogen-substituted glass tube and a stirrer. 40 parts by weight of methacrylate and 200 parts by weight of ethyl alcohol are added, and α,
1.2 parts by weight of α'-azobisisobutyronitrile was added, and the mixture was refluxed and heated at 80 ° C. under nitrogen substitution to carry out polymerization for 4 hours.

Next, 56 parts by weight of cyclohexylamine was added to a solution of 54 parts by weight of monochloroacetic acid dissolved in 110 parts by weight of ethanol to neutralize monochloroacetic acid, and this solution was dropped into a flask with a dropping funnel. Further, an amphoteric reaction was carried out at 80 ° C. for 4 hours under a nitrogen stream to obtain a highly viscous solution having a resin content of 50 parts by weight. When the water solubility of the obtained polymer was measured by the same method as in Production Examples 1 to 10, the transmittance was as good as 70% or more.

A hair gel comprising 4% by weight of this highly viscous solution, 0.5% by weight of gel base and the balance of pure water (95.5% by weight) was prepared and evaluated in the same manner as in Example 6. . Table 2 shows the results. The evaluation method is as follows.

(1) Setting force 2.0 g of a hair bundle having a length of 23 cm was immersed in the gel composition, pulled out, lightly squeezed, wound around a rod having a diameter of 1 cm, dried and then taken out from the rod to obtain a curled product. Was. The set force was evaluated from the degree of extension of the hair bundle after vertically suspending the hair bundle for 30 minutes in a thermo-hygrostat that had been conditioned for 3 hours at 20 ° C. and 80% humidity for 3 hours. ○ = almost no change. Δ = Slight elongation is observed. × = Elongation is clearly observed. (2) Transmittance The transmittance of the gel composition in a 1 cm × 1 cm cell at a wavelength of 655 nm was measured. (3) Strength The viscosity of the gel composition was measured using a B8H type viscometer, and 6. The rotation speed was measured at 10 rpm and 20 rpm.

[0093]

[Table 2] Table 2 shows that the gel composition of the present invention has a higher transmittance than the gel composition using the conventional zwitterionic polymer. This is because the amine oxide group-containing water-soluble resin of the present invention has higher compatibility with a gel base (cosmetic base material) than conventional zwitterionic polymers, and does not cause turbidity when formed into a gel composition. .

[0094]

The present invention provides various hair cosmetics, such as hair sprays, mousses, set lotions, gels, etc., which are excellent in adhesion to hair and have good setting power or conditioning effect and feeling. Can be.

Claims (9)

[Claims] (1) a weight average molecular weight of 5,000 to 1,000
Hair cosmetics containing 0000 amine oxide group-containing water-soluble resins. 2. The water-soluble resin comprises: (A) a hydrophilic monomer containing an amine oxide group-containing monomer: 15 to 100% by weight; and (B) a hydrophobic monomer: 85 to 0% by weight. The hair cosmetic according to claim 1, which is obtained by polymerization. 3. The hair cosmetic according to claim 2, wherein the amine oxide group-containing monomer as the component (A) is an amine oxide group-containing ethylenically unsaturated monomer. 4. The hair cosmetic according to claim 2, wherein the amine oxide group-containing monomer of the component (A) is at least one compound selected from the formulas (I) to (VI). Embedded image (Wherein, R ¹ is a hydrogen atom or a methyl group, R ² and R ³ are a C ₁ -C ₂₄ alkyl group which may be the same or different,
An aryl group of C ₆ -C _24, or an arylalkyl group of C ₇ -C _24, alkyl group of R ⁴ and R ⁵ are C ₁ ~C _24, C ₆ ~
Aryl group of C _24, or aryl alkyl radical of C ₇ -C _24, an X represents a divalent linking group, m is an integer of 0 to 1, n is an integer of 0 to 4, p is 0 to 3 And Y is the following: Other R ^{6 to} R ¹³ are a hydrogen atom or a C _{1 to} C ₂₄ alkyl group, a C _{6 to} C ₂₄ aryl group, or a C _{7 to} C ₂₄ arylalkyl group, and a and b are the same or different. Good one
And an integer of 10 to 10. ) 5. The hair cosmetic according to claim 2, wherein the proportion of the amine oxide group-containing monomer in all the monomers used for the water-soluble resin is 30% by weight or more. 6. The hair cosmetic composition according to claim 1, wherein the water-soluble resin is obtained by polymerizing a monomer containing a nitrogen-containing precursor monomer and then oxidizing the polymerized monomer. . 7. The hair cosmetic according to claim 6, wherein the nitrogen-containing precursor monomer is an ethylenically unsaturated monomer. 8. The method according to claim 1, wherein the nitrogen-containing precursor monomer has the formula (V):
(VIII) at least one compound selected from
The hair cosmetic according to claim 6. Embedded image (The definitions of R ^{1 to} R ¹⁰ , a, b, m, n, p, X, and Y in the formula are the same as those in the formulas (I) to (IV).) 9. The hair cosmetic according to claim 6, wherein the proportion of the nitrogen-containing precursor monomer in all the monomers used for the water-soluble resin is 30% by weight or more.