JP2003034704A - Cationic polymer providing conditioning effect - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a cationic polymer improved for stickiness and stiffness at drying and conditioning effect at rinsing for hair cosmetics, while got rid of twitching and improved for stickiness and sliminess for skin cosmetics. SOLUTION: The amino acid-modified cationic polymer is obtained by neutralizing an amino acid-modified water soluble polymer having an amino acid on the side chain with an inorganic acid and/or an organic acid. The amino acid-modified water soluble polymer having an amino acid on the side chain is a polymer comprising repeating unit of a basic amino acid-modified polymerizable monomer as the main component and/or a copolymer of the above monomer with a kind of monomer selected from monomers having ethylenic and allylic double bonds.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION The present invention has good adsorptivity to hair and skin, and when incorporated into a cosmetic for hair, provides smooth finger passage during rinsing and is soft and non-greasy after drying. A cationic polymer that gives excellent conditioning properties such as a finishing feel and, when incorporated into a skin cosmetic, improves a tightness and gives a non-greasy, dry feel, and a cosmetic composition containing the cationic polymer. It is about.

[0002]

2. Description of the Related Art In cosmetics for hair such as shampoos and rinses, anionic surfactants are generally used for imparting detergency. However, during cleaning, oil and fat components of hair are removed more than necessary, and after cleaning, The smoothness of the hair is lost, the hair feels dry and hard, and combing becomes poor, which may cause problems such as easy occurrence of split hairs and split ends. Furthermore, these symptoms are promoted by entanglement of hair during washing and rinsing. Further, although anionic surfactants are commonly used in skin cosmetics, there is a problem in that the skin feels taut. In order to eliminate such inconvenience, a conditioning agent is incorporated into cosmetic compositions such as hair cosmetics and skin cosmetics.

In the case of cosmetics for hair, it is essential that the conditioning agent is adsorbed to the hair, and as a substance that gives a conditioning effect, a cationic water-soluble polymer having an adsorption function based on ionicity and a chemical adsorption effect are used. There are amino acid derivatives and the like utilizing. As the former, a water-soluble polymer obtained by introducing quaternary nitrogen into a polysaccharide such as a cellulose derivative or guar gum or starch is used. For example, Japanese Patent Publication No. 47-20635 discloses a cation-modified cellulose derivative which is a cellulose derivative having quaternary nitrogen introduced into shampoo and hair cosmetics. Further, Japanese Patent Publication No. 60-42761 discloses cation-modified starch having quaternary nitrogen introduced therein, and Japanese Patent Publication No. 7-17491 discloses cation-modified guar gum containing cation-modified guar gum as hair care products such as shampoo and rinse. Is used for. Furthermore, JP-A-1
JP-A-128914 discloses a shampoo composition containing a copolymer of a dialkyldiallylammonium salt and a quaternary nitrogen-introduced cellulose derivative.
Further, these cationic water-soluble polymers have been blended in skin cosmetics such as body soaps because of the effects of modifying the foam such as obtaining creamy foam quality and imparting a moist feeling to the skin.

On the other hand, an alkyl quaternary ammonium salt such as alkyltrimethylammonium chloride is most widely used as a substance which gives a conditioning effect by a chemical adsorption action. Recently, amidoamine compounds and amino acid derivatives such as collagen protein hydrolysates have been used. For example, Japanese Patent Laid-Open No. 8-32
Japanese Patent No. 5122 discloses a shampoo composition containing an amidoamine compound, a cationic polymer and an amphoteric surfactant. Further, JP-A-11-106314 discloses a basic amino acid derivative obtained by reacting an epoxy alkane with a basic amino acid.
In particular, amino acid derivatives have an adsorption amount on hair of pH 6 to
7 is the largest, and the adsorption amount increases as the degree of hair damage increases.

In the case of skin cosmetics such as body soap, a moisturizing agent such as glycerin is incorporated to eliminate the feeling of sensation.

[0006]

A cationic water-soluble polymer such as a cation-modified cellulose derivative forms a complex salt with an anionic surfactant at the time of washing the hair and is adsorbed to the hair.
While showing an excellent conditioning effect during rinsing,
There is a problem that a sticky feeling or a stiff feeling remains after drying and the feeling becomes bad. In addition, cation-modified guar gum is
Although it does not feel sticky after drying, the amount of adsorption is small,
There is a problem that the conditioning effect during rinsing is weak. Copolymers of dialkyldiallylammonium salts and the like have a smooth dry feel, but have a problem that the amount of adsorption is small and the conditioning effect is weak.
Further, in the case of a copolymer in which the composition ratio of the dialkyldiallylammonium salt is increased in order to increase the adsorption amount, the adsorption amount increases, but there is a problem that the stickiness after drying increases. Further, when an ionic functional group is introduced into a polymer compound, even if the amount is small, it has a great influence on the physical and chemical properties of the polymer. For example, a cation-modified cellulose derivative, a cation-modified guar gum, a copolymer of a dialkyldiallylammonium salt, and the like have a quaternary ammonium base, which is a cationic functional group, in the molecule so that they can be mixed with an anionic polymer. Occurrence of complex salts is observed, and restrictions are imposed on the formulation. But,
Those having a tertiary amino group in the molecule are not affected by this effect.

On the other hand, the amino acid derivative has an appropriate amount of adsorption to the hair, but it is easy to fall off during rinsing, and in a rinse-off product such as shampoo, the conditioning effect cannot be expected so much, and a water-soluble polymer such as a cationic polymer is included in the formulation. Added to supplement the effect. Therefore, these substances are mainly applied to hair rinses and hair treatments.

Further, although amidoamine compounds are excellent in biodegradability and low irritation, etc., they have a small amount of adsorption to hair and the like, and thus have other properties such as alkyl quaternary ammonium salts, quaternized polypeptide compounds and cationic water-soluble polymers. It is used as a cosmetic composition when used in combination with the conditioning agent. Further, the alkyl quaternary ammonium salt has a large irritation to the skin and the eye mucous membrane, and development of a conditioning agent to replace the alkyl quaternary ammonium salt is required.

Although a conditioning agent such as a cationic water-soluble polymer or a moisturizing agent such as glycerin eliminates the feeling of tightness, it may cause a sticky feeling or a slimy feeling depending on the blending amount in the formulation.

[0010]

In such a situation, the present invention has an appropriate adsorption action of amino acid derivatives on hair, maintains a conditioning effect without dropping during rinsing, and has a conventional cationic water-soluble polymer. As a result of diligent studies to improve the sticky feeling and dry feeling of dryness, the weakness of conditioning effect at the time of rinsing, and further to eliminate the tight feeling on the skin and to improve the sticky feeling and the slimy feeling. An amino acid-modified water-soluble polymer having an amino acid in a side chain and / or a monomer composed mainly of an amino acid-modified polymerizable monomer A copolymer of a monomer and one kind of monomer selected from monomers having an ethylenic and allylic double bond,
The inventors have found that an amino acid-modified cationized polymer obtained by neutralizing an amino acid-modified water-soluble polymer having an amino acid in its side chain with an acid can meet this purpose, and completed the present invention.

Regarding the amino acid-modified polymer, Japanese Patent Application Laid-Open No. Sho 60
However, the amino acids are limited to optically active amino acids. Also,
The obtained amino acid-modified polymer can be optically resolved by forming a salt of a transition metal such as Cu, Ni or Co. Further, this product can be used as an inorganic carrier such as silica gel or glass beads, or a polystyrene gel or polyacrylamide gel. It has been shown that it can be used as a packing material for liquid chromatography having optical resolution by being supported on a carrier by physical adsorption such as coating or chemical bonding on the organic carrier. However, there is no indication that this amino acid-modified polymer is used as a conditioning agent for cosmetics. Furthermore, the amino acid-modified cationized polymer of the present invention uses an amino acid in an amino acid-modified water-soluble polymer having an amino acid in a side chain as a basic amino acid, and neutralizes the amino group portion of the basic amino acid with an acid to give a cation. In the form of a water-soluble polymer having a property, the water-soluble polymer having a cationic property exerts an excellent effect as a conditioning agent. Therefore, the amino acid modified polymer is Cu,
By using a salt of a transition metal such as Ni or Co, the amino acid-modified cationized polymer of the present invention is different from the packing material for liquid chromatography having optical resolution in structure, physical properties and function.

Further, as an amino acid-based polymer, JP-A-200
No. 0-119233, the nitrogen atom of the amino group in the amino acid is bound by a crosslinking agent such as a polyepoxy compound.
It has been shown that a polyamino acid derivative has an excellent effect in moisturizing, imparting gloss to hair, treating effect, and imparting wettability to hair and skin in cosmetic applications. However, since these substances are polyamino acids in which amino groups in amino acids are bound to each other and the main chain has an amino acid structure, the amino groups in the amino acids do not sufficiently function as hydrophilic groups, and the amino groups in the amino acids above a certain level are not used. When it becomes a high molecular weight polymer, it has the property of lacking stability in solvents including water. Therefore, the amino acid-modified cationized polymer of the present invention, which is water-soluble and has a conditioning effect during washing, is also different in structure, physical properties, and function.

The amino acid-modified water-soluble polymer of the present invention can be obtained by reacting a polymerizable monomer having a reactive group with an amino acid with an amino acid as one synthetic method.
The amino acid-modified polymerizable monomer can be obtained by a conventionally known polymerization method. Similarly, when the amino acid-modified water-soluble polymer is a copolymer, an amino acid-modified polymerizable monomer and one kind of monomer selected from monomers having an ethylenic and allylic double bond are also included. Can be obtained by copolymerization by a conventionally known polymerization method. Examples of these polymerization methods include a radical polymerization method using a peroxide or an azo compound as an initiator, an ionic polymerization method using a Grignard reagent or an alkyl metal, and a radiation polymerization method. As another synthetic method, it can be obtained by polymerizing a polymerizable monomer having a reactive group with an amino acid by the above-mentioned polymerization method and then reacting with the amino acid. In the case of, a polymerizable monomer having a reactive group with an amino acid and one kind of monomer selected from monomers having an ethylenic and allylic double bond were polymerized by the above polymerization method. It can also be obtained later by reacting with an amino acid. Furthermore, it is also possible to polymerize by a previous polymerization method while reacting a polymerizable monomer having a reactive group with an amino acid with an amino acid. Similarly, in the case of a copolymer, the reactivity with an amino acid is It is also possible to copolymerize with one kind of monomer selected from monomers having ethylenic and allylic double bonds by the above-mentioned polymerization method while reacting a polymerizable monomer having a group with an amino acid. Is. However, the synthetic method for obtaining the amino acid-modified water-soluble polymer of the present invention can be performed by any synthetic method, and is not limited to these methods.

The method of adding and modifying an amino acid to a polymerizable monomer is carried out by the following chemical formula (1) and / or the following chemical formula (2)
The oxirane compound represented by can be reacted under alkaline conditions with an organic solvent such as a lower alcohol or a polyhydric alcohol, or a mixed solvent of these organic solvents and water. For example, it can be easily synthesized by the method described in JP-A-48-22417. However, in the case of arginine, it is possible to react with an oxirane compound without being under alkaline conditions.

At this time, by adding a polymerization initiator or the like into the reaction system of the amino acid and the polymerizable monomer, the addition reaction with the amino acid and the polymerization reaction can be simultaneously carried out. When a copolymer is obtained, a monomer selected from a polymerization initiator and a monomer having an ethylenic and allylic double bond in the reaction system of an amino acid and a polymerizable monomer. The addition reaction with the amino acid and the copolymerization reaction can be carried out at the same time.

[0016] (In the formula, R ₁ is hydrogen, an alkyl group having 1 to 3 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, R ₂ is hydrogen, a carboxymethyl group or an alkyl group having 1 to 3 carbon atoms, R ₃ , R ₄
And R ₅ each represent hydrogen or an alkyl group having 1 to 3 carbon atoms)

[0017] (In the formula, R ₁ is hydrogen, an alkyl group having 1 to 3 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, R ₂ is hydrogen, a carboxymethyl group or an alkyl group having 1 to 3 carbon atoms, R ₃ , R ₄
And R ₅ each represent hydrogen or an alkyl group having 1 to 3 carbon atoms)

On the other hand, a polymerizable monomer having a reactive group with an amino acid, that is, an oxirane compound is polymerized by a conventionally known polymerization method such as a radical polymerization method, an ionic polymerization method, a radiation polymerization method, and the following chemical formula (3) And / or a high molecular weight oxirane compound having a reactive group with an amino acid represented by the following chemical formula (4), a lower alcohol,
The amino acid-modified water-soluble polymer which is the substance of the present invention can also be obtained by reacting with an amino acid in an organic solvent such as a polyhydric alcohol or a mixed solvent of these organic solvents and water. In the case of a copolymer, an oxirane compound and one kind of monomer selected from monomers having an ethylenic and allylic double bond are polymerized by a conventionally known polymerization method to form a reactive group with an amino acid. It can also be obtained by reacting a high molecular weight copolymer oxirane compound having the above with an amino acid in an organic solvent such as a lower alcohol or a polyhydric alcohol, or a mixed solvent of these organic solvents and water.

[0019] (In the formula, R ₁ is hydrogen, an alkyl group having 1 to 3 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, R ₂ is hydrogen, a carboxymethyl group or an alkyl group having 1 to 3 carbon atoms, R ₃ , R ₄
And R ₅ are each hydrogen or an alkyl group having 1 to 3 carbon atoms,
m represents an integer of 40 or more)

As the polymerizable monomer having an amino acid-reactive group which constitutes the amino acid-modified water-soluble polymer according to the present invention, glycidyl methacrylate having an epoxy group represented by the chemical formula (1), glycidyl acrylate, glycidyl An oxirane compound having an ethylenic double bond such as sorbate, glycidyl metaitaconate, ethyl glycidyl malate, and glycidyl vinyl sulfonate, allyl glycidyl ether having an epoxy group represented by the chemical formula (2), and methallyl glycidyl Ether, allyl-methyl glycidyl ether, methallyl-
Examples thereof include oxirane compounds having an allylic double bond such as methyl glycidyl ether. Each of these oxirane compounds can be used alone,
It is also possible to use a mixture of two or more kinds. Of these, glycidyl methacrylate, glycidyl acrylate, allyl glycidyl ether, and methallyl glycidyl ether are preferable.

[0021] (In the formula, R ₁ is hydrogen, an alkyl group having 1 to 3 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, R ₂ is hydrogen, a carboxymethyl group or an alkyl group having 1 to 3 carbon atoms, R ₃ , R ₄
And R ₅ are each hydrogen or an alkyl group having 1 to 3 carbon atoms,
m represents an integer of 40 or more)

As the basic amino acid that reacts with the polymerizable monomer, any natural or synthetic amino acid can be used.
For example, lysine, histidine, arginine, ornithine, hydroxylysine and the like can be mentioned. One of these amino acids may be used alone, or two or more of them may be mixed and used. Of these amino acids, arginine is preferable. Further, any of D body, L body and DL body can be used.

Among the basic amino acids, for example, in the case of arginine, a compound in which two molecules of the oxirane compound are added to one molecule of the basic amino acid may be used.

When the oxirane compound that reacts with the basic amino acid is a high molecular weight oxirane compound represented by the chemical formula (3) and / or the chemical formula (4), arginine can be added in the same manner as the oxirane compound which is a polymerizable monomer. In this case, a compound represented by the following chemical formula (5) and / or the following chemical formula (6) in which two oxirane compound segments constituting a polymer are added to one molecule of basic amino acid may be used. Furthermore, when the oxirane compound segment is a copolymer with one kind of monomer selected from monomers having an ethylenic and allylic double bond, the following chemical formula (7) and / or the following chemical formula (8) ).

[0025] (In the formula, R ₁ is hydrogen, an alkyl group having 1 to 3 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, R ₂ is hydrogen, a carboxymethyl group or an alkyl group having 1 to 3 carbon atoms, R ₃ , R ₄
And R ₅ are each hydrogen or an alkyl group having 1 to 3 carbon atoms,
m and n each represent an integer of 40 or more)

However, it is particularly preferred that one oxirane compound, which is a polymerizable monomer, be added to one basic amino acid molecule.
The polymer of the basic amino acid-modified polymerizable monomer to which the molecule is added and the oxirane compound segment constituting the polymer are 1
It is a compound with individual additions.

[0027] (In the formula, R ₁ is hydrogen, an alkyl group having 1 to 3 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, R ₂ is hydrogen, a carboxymethyl group or an alkyl group having 1 to 3 carbon atoms, R ₃ , R ₄
And R ₅ are each hydrogen or an alkyl group having 1 to 3 carbon atoms,
m and n each represent an integer of 40 or more)

The product obtained by the reaction of an oxirane compound and an amino acid is not usually a single compound, but is composed of one basic amino acid molecule with one molecule of the oxirane compound added and a mixture with two or more molecules added. These mixtures may be isolated and purified into a single compound by, for example, chromatography and the like, and one of them may be blended into cosmetics as the substance of the present invention and used, or the mixture may be used without isolation and purification. You can use it as it is. Furthermore, the reaction product of the oxirane compound reacting with the organic solvent or water, and the unreacted basic amino acid may be present in the mixture, but the proportion thereof is preferably 30% or less. If it exceeds 30%, the original conditioning effect may be impaired when incorporated into a cosmetic composition.

[0029] (In the formula, R ₁ is hydrogen, an alkyl group having 1 to 3 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, R ₂ is hydrogen, a carboxymethyl group or an alkyl group having 1 to 3 carbon atoms, R ₃ , R ₄
And R ₅ are each hydrogen or an alkyl group having 1 to 3 carbon atoms,
Y is one kind of monomer selected from monomers having an ethylenic and allylic double bond, k and l are each 1 or more, and k + m and l + n are each an integer of 40 or more)

As the acid for neutralizing the amino acid-modified water-soluble polymer, inorganic acids such as hydrochloric acid, sulfuric acid, carbonic acid and phosphoric acid, acetic acid,
Organic acids such as citric acid, lactic acid, malic acid, glycolic acid, tartaric acid, glutamic acid and / or its derivative, aspartic acid and / or its derivative, and pyrrolidonecarboxylic acid can be used. Particularly preferred acids include hydrochloric acid, acetic acid, citric acid, lactic acid and glycolic acid.

[0031] (In the formula, R ₁ is hydrogen, an alkyl group having 1 to 3 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, R ₂ is hydrogen, a carboxymethyl group or an alkyl group having 1 to 3 carbon atoms, R ₃ , R ₄
And R ₅ are each hydrogen or an alkyl group having 1 to 3 carbon atoms,
Y is one kind of monomer selected from monomers having an ethylenic and allylic double bond, k and l are each 1 or more, and k + m and l + n are each an integer of 40 or more)

By neutralizing with these acids, the amino group in the amino acid-modified water-soluble polymer becomes cationic,
The amino acid-modified cationized polymer of the present invention is obtained.
The amount of the acid at this time is preferably 0.2 to 1.0 per 1 polymerizable monomer segment which has reacted with the basic amino acid and constitutes the amino acid-modified water-soluble polymer of the present invention. For example, when the amino acid is arginine, a cationic polymer having a structure represented by the following chemical formula (9) and / or the following chemical formula (10) can be obtained. Similarly, in the case of a copolymer with one kind of monomer selected from monomers having an ethylenic and allylic double bond, the following chemical formula (1
1) and / or a cationic polymer having a structure represented by the following chemical formula (12) can be obtained.

[0033] (In the formula, R ₁ is hydrogen, an alkyl group having 1 to 3 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, R ₂ is hydrogen, a carboxymethyl group or an alkyl group having 1 to 3 carbon atoms, R ₃ , R ₄
And R ₅ are each hydrogen or an alkyl group having 1 to 3 carbon atoms,
m is 0 or more, m + n is 40 or more, and 0.2 ≦
n / (m + n) ≦ 1.0, X ⁻ represents an anion)

[0034] (In the formula, R ₁ is hydrogen, an alkyl group having 1 to 3 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, R ₂ is hydrogen, a carboxymethyl group or an alkyl group having 1 to 3 carbon atoms, R ₃ , R ₄
And R ₅ are each hydrogen or an alkyl group having 1 to 3 carbon atoms,
m is 0 or more, m + n is 40 or more, and 0.2 ≦
n / (m + n) ≦ 1.0, X ⁻ represents an anion)

As the method of neutralization, the above-mentioned method of neutralizing the amino acid-modified water-soluble polymer with a required amount of acid and the basic amino acid-modified polymerizable monomer neutralized with the required amount of acid are first described. It can also be obtained by polymerization according to the polymerization method shown.

[0036] (In the formula, R ₁ is hydrogen, an alkyl group having 1 to 3 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, R ₂ is hydrogen, a carboxymethyl group or an alkyl group having 1 to 3 carbon atoms, R ₃ , R ₄
And R ₅ are each hydrogen or an alkyl group having 1 to 3 carbon atoms,
m is 0 or more, l is 1 or more, l + m + n is 40 or more, and an integer of 0.2 ≦ n / (m + n) ≦ 1.0,
Y is one kind of monomer selected from monomers having an ethylenic and allylic double bond, and X ⁻ represents an anion)

Among the monomers having an ethylenic and allylic double bond used as a monomer for copolymerization with an oxirane compound in the present invention, acrylamide, methacrylamide, N-methylolacrylamide, N-alkyl acrylamide, vinyl acetate, acrylic acid esters, vinyl alcohol, vinyl pyrrolidone, vinyl acetamide, diacetone acrylamide,
2-hydroxyethyl methacrylate, 2-methacrylic acid
Hydroxypropyl, 2-methoxyethyl methacrylate, 2-ethoxyethyl methacrylate, 2-acrylic acid
Hydroxyethyl, 2-hydroxypropyl acrylate, 2-methoxyethyl acrylate, 2-ethoxyethyl acrylate, methoxypolyethylene glycol methacrylate, ethylene glycol dimethacrylate, 2-methacryloyloxyethyl succinate, 2-methacryloyloxy maleate. Ethyl, polyethylene glycol dimethacrylate, methacryloylethyl dimethyl betaine,
N-methacryloyloxyethyl N, N-dimethylammonium-α-methylcarboxybetaine, allyloxy-hydroxypropyl-hydroxyethylcellulose, allyl alcohol, acrylic acid, methacrylic acid, crotonic acid, 2-acrylamido-2-methylpropanesulfonic acid, vinyl Sodium sulfonate, acrylamidoglycolic acid, 2-acrylamido-2-methylpropanephosphonic acid, sodium vinylphosphonate, allylphosphonic acid, reaction product of glycidyl acrylate with acidic and neutral amino acids, glycidyl methacrylate with acidic and neutral amino acids , A reaction product of allyl glycidyl ether with acidic and neutral amino acids, a reaction product of methallyl glycidyl ether with acidic and neutral amino acids, more preferably, Acrylamide, N- methylol acrylamide, methoxypolyethylene glycol methacrylate, allyloxy - hydroxypropyl - hydroxyethylcellulose, and methacrylic acid, acrylic acid. Each of these may be a commercially available product, and acrylamide is a trade name of acrylic amide (Mitsubishi Chemical Corporation).
N-methylol acrylamide is a trade name N-methylol acrylamide (manufactured by Nakarai Desk Co., Ltd.), and methoxy polyethylene glycol methacrylate is a trade name ME-15, ME-20 and ME-100 (Toho Chemical Industry Co., Ltd. ), Allyloxy-hydroxypropyl-hydroxyethyl cellulose is a trade name Tylos
e HL 40YP2 AM (manufactured by Clariant Polymer Co., Ltd.), methacrylic acid is trade name methacrylic acid (manufactured by Mitsubishi Rayon Co., Ltd.), acrylic acid is trade name acrylic acid 100% (manufactured by Mitsubishi Chemical Co., Ltd.) It is easily available.

[0038] (In the formula, R ₁ is hydrogen, an alkyl group having 1 to 3 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, R ₂ is hydrogen, a carboxymethyl group or an alkyl group having 1 to 3 carbon atoms, R ₃ , R ₄
And R ₅ are each hydrogen or an alkyl group having 1 to 3 carbon atoms,
m is 0 or more, l is 1 or more, l + m + n is 40 or more, and an integer of 0.2 ≦ n / (m + n) ≦ 1.0,
Y is one kind of monomer selected from monomers having an ethylenic and allylic double bond, and X ⁻ represents an anion)

The content of the amino acid-modified cationized polymer of the present invention in the cosmetic is preferably 0.1 to 5% by weight. If it is less than 0.1% by weight, the effect is not sufficiently exhibited.
If the content exceeds 10% by weight, a sticky feeling or a stiff feeling is generated after use and the usability deteriorates.

The amino acid-modified cationized polymer of the present invention is mixed in a prescribed amount in a known system by a known formulation to obtain the cosmetic composition of the present invention. However, other components in the cosmetic composition are not particularly limited, Ingredients commonly used in foods can be added as optional ingredients. Other components that can be blended are illustrated below.

Examples of anionic surfactants include alkyl (C8-24) sulfates and alkyl (C8-8).
4) Ether sulfate, alkyl (C8-24) benzene sulfonate, alkyl (C8-24) phosphate, polyoxyalkylene alkyl (C8-24)
Ether phosphate, alkyl (C8-24) sulfosuccinate, polyoxyalkylene alkyl (C8
~ 24) ether sulfosuccinate, acyl (8 carbon atoms
To 24) alanine salt, acyl (8 to 24 carbon atoms) glutamate, acyl (8 to 24 carbon atoms) isethionate salt, acyl (8 to 24 carbon atoms) sarcosinate salt, acyl (8 carbon atoms) To 24) modified taurine salt, acyl (8 to 24 carbon atoms) methyl taurine salt, α-sulfo fatty acid ester salt, ether carboxylate, polyoxyalkylene fatty acid monoethanolamide sulfate, long chain (8 to 8 carbon atoms)
24) Carboxylic acid salts and the like can be mentioned.

As the nonionic surfactant, alkanolamide, glycerin fatty acid ester, polyoxyalkylene alkyl ether, polyoxyalkylene glycol ether, polyoxyalkylene sorbitan fatty acid ester, sorbitan fatty acid ester, polyoxyalkylene sorbit fatty acid ester, sorbit fatty acid ester. , Polyoxyalkylene glycerin fatty acid ester, polyoxyalkylene fatty acid ester, polyoxyalkylene alkyl phenyl ether, tetrapolyoxyalkylene ethylenediamine condensate, sucrose fatty acid ester, polyoxyalkylene fatty acid amide, polyoxyalkylene glycol fatty acid ester, polyoxy Alkylene castor oil derivative, polyoxyalkylene hydrogenated castor oil derivative, Le Kill polyglycosides, polyglycerol fatty acid esters, and the like.

As the amphoteric surfactant, alkyl (C8-24) amidopropyl betaine, alkyl (C8-24) carboxybetaine, alkyl (C8)
~ 24) Sulfobetaine, Alkyl (C8-24)
Hydroxysulfobetaine, alkyl (8 to 2 carbon atoms
4) Aminocarboxylic acid, alkyl (C8-24) imidazolinium betaine, alkyl (C8-24)
Examples thereof include amine oxides, alkyl (C 8-24) phosphates containing tertiary nitrogen and quaternary nitrogen, and the like.

As the polymer, anionic, cationic,
Nonionic or amphoteric polymers can be blended. Examples of anionic polymers include acrylic acid derivatives (polyacrylic acid and its salts, acrylic acid / acrylamide /
Ethyl acrylate copolymer and its salts, etc.), Methacrylic acid derivatives (polymethacrylic acid and its salts, methacrylic acid / acrylamide / diacetone acrylamide / acrylic acid alkyl ester / methacrylic acid alkyl ester copolymers and its salts, etc.), Crotonic acid derivative (vinyl acetate / crotonic acid copolymer, etc.), maleic acid derivative (maleic anhydride / diisobutylene copolymer, isobutylene /
Maleic acid copolymer, etc.), polyglutamic acid and its salt, hyaluronic acid and its salt, carboxymethyl cellulose, carboxyvinyl polymer and the like.

Examples of the cationic polymer include quaternary nitrogen-modified polysaccharides (cation-modified cellulose derivative, cation-modified guar gum, cation-modified locust bean gum, cation-modified starch, etc.), dimethyldiallylammonium chloride derivative (dimethyldiallyl chloride). Ammonium / acrylamide copolymer, poly (dimethylmethylene piperidinium chloride), vinylpyrrolidone derivative (vinylpyrrolidone / dimethylaminoethylmethacrylic acid copolymer salt, vinylpyrrolidone / methacrylamidopropyltrimethylammonium chloride copolymer,
Vinylpyrrolidone / methylvinylimidazolium chloride copolymer, etc.), methacrylic acid derivative (methacryloylethyldimethylbetaine / methacryloylethyltrimethylammonium chloride / methacrylic acid 2-hydroxyethyl copolymer, methacryloylethyldimethylbetaine / methacryloylethyltrimethylammonium chloride) Methoxy polyethylene glycol copolymer etc.)
Etc.

Examples of the nonionic polymer include acrylic acid derivatives (hydroxyethyl acrylate / methoxyethyl acrylate copolymer, polyacrylic acid amide, etc.), vinylpyrrolidone derivatives (polyvinylpyrrolidone, vinylpyrrolidone / vinyl acetate copolymer). Etc.), polyoxyalkylene glycol derivatives (polyethylene glycol, polypropylene glycol, etc.), cellulose derivatives (methyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, etc.), polysaccharides and their derivatives (guar gum, locust bean gum, dextran, etc.), polyamide epichlorohydrin Resin etc. are mentioned.

Examples of the amphoteric polymer include dimethyldiallylammonium chloride derivatives (acrylamide / acrylic acid / dimethyldiallylammonium chloride copolymers, acrylic acid / dimethyldiallylammonium chloride copolymers), methacrylic acid derivatives (polymethacryloylethyl). Dimethyl betaine, N-methacryloyloxyethyl N, N-dimethylammonium-α-methylcarboxybetaine / alkyl methacrylate copolymer, etc.) and the like.

Examples of the oil component include olive oil, jojoba oil, liquid paraffin, fatty acid alkyl ester and the like. Examples of the pearling agent include fatty acid ethylene glycol, and examples of the suspending agent include polystyrene emulsion.

Other components include cationic surfactants, solubilizers (ethanol, ethylene glycol, propylene glycol, etc.), moisturizers (glycerin, sorbitol, maltitol, dipropylene glycol, 1,3).
-Butylene glycol, hyaluronic acid, etc.), antioxidants, silicones and silicone derivatives, higher alcohols, higher fatty acids, thickeners, sequestering agents (edetate salts, etc.), pH adjusters, UV absorbers, bactericides, preservatives Agents, pigments, fragrances, foam enhancers and the like.

In still another embodiment, the organic acid and / or inorganic acid of the amidoamine compound and the higher fatty acid and / or
Alternatively, higher alcohols can be added.

[0051]

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

Example 1 L-lysine 50% aqueous solution 29.4 g (0.1 mol) was dissolved in 11 wt% isopropanol aqueous solution 181.5 g, and then 48% sodium hydroxide aqueous solution 8.3 g.
(0.1 mol) was added and uniformly dissolved. Glycidyl methacrylate (hereinafter referred to as GMA) heated to 40 ° C 1
4.2 g (0.1 mol) was added dropwise over 6 hours. After the dropping, the temperature is raised to 60 ° C. and the reaction is performed at the same temperature for 10 hours. After the reaction, the temperature was cooled to 30 ° C or lower, and 35% hydrochloric acid 20.9 g (0.2 m
ol) to neutralize. After neutralization, nitrogen is introduced and deoxidation is performed for 2 hours. After deoxidation, the temperature was raised to 80 ° C., 0.2 g of ammonium persulfate was added, and polymerization was carried out for 2 hours. After 2 hours, 0.2 g of the same amount of ammonium persulfate is further added, and polymerization is further performed at the same temperature for 3 hours. After the completion of the polymerization reaction, the pH was adjusted to 5 to 7, and then isopropanol was removed under reduced pressure to obtain 220 g of a 17% aqueous solution of the compound of the present invention.

Example 2 30 wt of 17.4 g (0.1 mol) of L-arginine
% Isopropanol aqueous solution 104.4 g, and then heated to 40 ° C. and GMA 14.2 g (0.1 mo)
1) was added dropwise in 6 hours. After the dropping, the temperature is raised to 60 ° C. and the reaction is performed at the same temperature for 10 hours. After completion of the reaction, p with 35% hydrochloric acid
Prepared to H6-7. After adjustment, 335 g of distilled water is added, and further 7.2 g (0.1 mol) of acrylamide is added and dissolved, and then nitrogen is introduced and deoxidation is performed for 2 hours. After deoxidation, the temperature was raised to 55 ° C., 0.1 g of V-50 (azo initiator: Wako Pure Chemical Industries, Ltd.) was added, and polymerization was carried out for 6 hours. After 6 hours, 0.5 g of V-50 was further added, and polymerization was further carried out at the same temperature for 10 hours. After completion of the polymerization reaction, isopropanol was removed under reduced pressure to obtain 430 g of a 9% aqueous solution of the compound of the present invention.

Example 3 30 wt of 17.4 g (0.1 mol) of L-arginine
% Isopropanol aqueous solution 104.4 g, and then heated to 40 ° C. and GMA 14.2 g (0.1 mo)
1) was added dropwise in 6 hours. After the dropping, the temperature is raised to 60 ° C. and the reaction is performed at the same temperature for 10 hours. After completion of the reaction, p with 35% hydrochloric acid
Prepared to H6-7. After adjustment, 364 g of distilled water was added, and further 10.1 g of N-methylolacrylamide (0.1 m
ol) is added and dissolved, then nitrogen is introduced and deoxidation is performed for 2 hours. After deoxidation, the temperature was raised to 55 ° C., 0.1 g of V-50 (azo initiator: Wako Pure Chemical Industries, Ltd.) was added, and polymerization was carried out for 6 hours. After 6 hours, 0.5 g of V-50 was further added, and polymerization was further carried out at the same temperature for 10 hours. After completion of the polymerization reaction, isopropanol was removed under reduced pressure to obtain 462 g of a 9% aqueous solution of the compound of the present invention.

Example 4 30 wt of 17.4 g (0.1 mol) of L-arginine
% Isopropanol aqueous solution 104.4 g, and then heated to 40 ° C. and GMA 14.2 g (0.1 mo)
1) was added dropwise in 6 hours. After the dropping, the temperature is raised to 60 ° C. and the reaction is performed at the same temperature for 10 hours. After completion of the reaction, p with 35% hydrochloric acid
Prepared to H6-7. After adjustment, 422 g of distilled water was added, and further 10.5 g of methoxypolyethylene glycol methacrylate (trade name ME-100: manufactured by Toho Chemical Industry Co., Ltd.).
(0.01 mol) is added and dissolved, then nitrogen is introduced and deoxidation is performed for 2 hours. After deoxidation, the temperature was raised to 55 ° C and V-5.
0 (azo initiator: manufactured by Wako Pure Chemical Industries, Ltd.) was added in an amount of 0.1 g, and 6
Polymerize for a period of time. After 6 hours, 0.5 g of V-50 was further added, and polymerization was further carried out at the same temperature for 10 hours. After completion of the polymerization reaction, isopropanol was removed under reduced pressure to obtain 521 g of an 8% aqueous solution of the compound of the present invention.

Example 5 30 wt of 17.4 g (0.1 mol) of L-arginine
% Isopropanol aqueous solution 104.4 g, and then heated to 40 ° C. and GMA 14.2 g (0.1 mo)
1) was added dropwise in 6 hours. After the dropping, the temperature is raised to 60 ° C. and the reaction is performed at the same temperature for 10 hours. After completion of the reaction, p with 35% hydrochloric acid
Prepared to H6-7. After the adjustment, 783 g of distilled water was added, and allyloxy-hydroxypropyl-hydroxyethyl cellulose (trade name Tylose HL40YP2A) was added.
M: 31.6 g of Clariant Polymer Co., Ltd.) was added and dissolved, then nitrogen was introduced and deoxidation was performed for 2 hours. After deoxidation, the temperature was raised to 55 ° C., 0.1 g of V-50 (azo initiator: Wako Pure Chemical Industries, Ltd.) was added, and polymerization was carried out for 6 hours. After 6 hours, 0.5 g of V-50 was added, and the mixture was added at the same temperature for 10 hours.
Polymerize for a period of time. After completion of the polymerization reaction, isopropanol was removed under reduced pressure to obtain a 7% aqueous solution of the compound of the present invention 897
g was obtained.

Example 6 30 wt of 17.4 g (0.1 mol) of L-arginine
% Isopropanol aqueous solution 104.4 g, and then heated to 40 ° C. and GMA 14.2 g (0.1 mo)
1) was added dropwise in 6 hours. After the dropping, the temperature is raised to 60 ° C. and the reaction is performed at the same temperature for 10 hours. After completion of the reaction, p with 35% hydrochloric acid
Prepared to H3-4. After the adjustment, 335 g of distilled water was added, and further 7.2 g (0.1 mol) of acrylic acid was added and dissolved, then nitrogen was introduced and deoxidation was performed for 2 hours. 55 after deoxidation
V-50 (azo initiator: Wako Pure Chemical Industries, Ltd.)
0.1 g is added and polymerization is carried out for 6 hours. After 6 hours, V-
0.5 g of 50 is added, and polymerization is further performed at the same temperature for 10 hours. After completion of the polymerization reaction, isopropanol was removed under reduced pressure to obtain 430 g of a 9% aqueous solution of the compound of the present invention.

Example 7 14.2 g (0.1 mol) of GMA was added to 24.0 g of isopropanol, nitrogen was introduced into the solution, and deoxidation was carried out for 2 hours. After deoxidation, the temperature is raised to 80 ° C., 0.1 g of AIBN (azobisbutylnitrile) is added, and polymerization is carried out at the same temperature for 10 hours. L-arginine 17.4 g (0.1 mol)
Is dissolved in 10 wt% isopropanol aqueous solution and then heated to 40 ° C. 37wt% G after temperature rise
38.2 g of MA polymer isopropanol solution is added dropwise in 6 hours. After the dropping, the temperature is raised to 60 ° C. and the reaction is performed at the same temperature for 10 hours. After completion of polymerization reaction, dilute with 220g of distilled water, pH
After adjusting to 5 to 7, isopropanol was removed under reduced pressure to obtain 295 g of an 11% aqueous solution of the compound of the present invention.

Example 8 After dissolving 17.4 g (0.1 mol) of L-arginine in 156.6 g of a 30% aqueous solution of isopropanol,
Nitrogen is introduced into the liquid and deoxidation is performed for 2 hours. Warm to 80 ° C. and add 0.2 g of ammonium persulfate. 14.2 g of GMA (0.1 mo
1) was added dropwise in 1 hour. After the dropping, 0.2 g of ammonium persulfate was further added, and the reaction was further performed at the same temperature for 2 hours. After completion of the polymerization reaction, the mixture was diluted with 95 g of distilled water and adjusted to pH 5 to 7, and then isopropanol was removed under reduced pressure to obtain 195 g of a 16% aqueous solution of the compound of the present invention.

Example 9 A shampoo having a composition shown in (A) of Table 1 was prepared using the amino acid-modified cationized polymers obtained in Examples 1 to 8. (12) of (A) in Table 1 is heated to 60 ° C,
After adding (1) with stirring to dissolve and confirming dissolution, (3) to (8) were added with stirring at 50 to 60 ° C. to homogenize, and (9) to (11) at 30 to 40 ° C. ) Was similarly added with stirring and mixed uniformly. Thus, the shampoos having the compositions shown in (A) of Table 1 were prepared, and the formulations of the present invention were prepared in the order of the inventive products obtained in Examples 1-8. As the standard product, a shampoo containing no amino acid-modified cationized polymer shown in the standard product (B) of Table 1 was prepared. (12) of (B) in Table 1 is heated to 60 ° C., and (3) to (8) are added with stirring at 50 to 60 ° C. to make the mixture uniform, and further at 30 to 40 ° C. (9) to ( Similarly, 11) was added while stirring and mixed uniformly. Thus, the shampoo having the composition shown in (B) of Table 1 was prepared and used as a standard product.

With respect to each shampoo prepared in (A) of Table 1, 10 testers evaluated the performance of the following items. Foaming when washing hair, fingers,
Feeling of wet hair, squeaky feeling after rinsing, softness after use (dry hair), moisturizing feeling, dry feeling,
The goodness of combing and the barbs were compared with the standard product prepared by the standard product (B) of Table 1, and the values were digitized by the methods of Tables 2 and 3 below, and the integrated value was obtained. The evaluation results are shown in Table 4.

[0062]

[Table 1]

Comparative Example 1 In order to compare the effect with the amino acid-modified cationized polymer used in the present invention, a cation-modified hydroxyethyl cellulose (catinal HC-100) having an ethylene oxide average addition mole number of 1.8 and a nitrogen content of 1.8% by weight. A shampoo having the composition shown in Comparative product (C) in Table 1 was prepared using Toho Chemical Industry Co., Ltd.). After heating (12) of (C) in Table 1 to 60 ° C. and adding (2) with stirring to dissolve, and confirming dissolution, (3) to (50) to 60 ° C.
(8) is added with stirring to make it uniform, and further 30-40
(9) to (11) were similarly added with stirring at 0 ° C. and mixed uniformly. Thus, a shampoo having the composition shown in (C) of Table 1 was prepared and designated as Comparative Product 1. As in Example 9, lathering during washing, fingering, feel of wet hair, and squeaky feeling after rinsing, softness after use (dry hair), moisturizing feeling, dry feeling, and good combability. And the gloss was compared with the standard product. The results are shown in Table 4.

[0064]

[Table 2]

[0065]

[Table 3]

Comparative Example 2 Similar to the shampoo formulation of Comparative Example 1, cation-modified guar gum (Catinal CG-100; manufactured by Toho Chemical Industry Co., Ltd.) having cationized guar gum, which is a galactomannan polysaccharide, has a nitrogen content of 1. 8% by weight), diallyldimethylammonium chloride / acrylamide copolymer (ME
Polymer 09W; manufactured by Toho Chemical Industry Co., Ltd.), N- [3
-Alkyloxy-2-hydroxypropyl] -L-arginine (composition component standard listed product according to makeup product type) was evaluated by combining the formulations (comparative products 2, 3, 4 in the order of description). The results are shown in Table 4.

[0067]

[Table 4]

The results in Table 4 show that the amino acid-modified cationized polymer, which is a neutralized product of the amino acid-modified water-soluble polymer with an organic acid and / or an inorganic acid, improved the shampoo performance.

It was also found that the amino acid-modified cationized polymer of the present invention is superior to the cation-modified hydroxyethyl cellulose in combing after use (dry hair), has a less sticky feeling, and gives a soft and silky feel. Furthermore, with cationized guar gum, which is a galactomannan polysaccharide, it is excellent in finger passage when washing hair, and has less squeaky feeling after rinsing, giving a smooth feel,
It was found that a dry feeling can be obtained after use (dry hair). Furthermore, with diallyldimethylammonium chloride / acrylamide copolymer, it has excellent slimy feel when washing hair, and also has less squeaky feeling after rinsing, and has a soft and moist feel after use (dry hair). Found to give. Furthermore, N
-[3-Alkyloxy-2-hydroxypropyl]-
Compared with L-arginine, it is excellent in foaming when washing hair,
It was found to give a dry feel after use.

Example 10 Using the amino acid-modified cationized polymers obtained in Examples 1 to 8, rinses having the compositions shown in Table 5 (A) were prepared.
A solution obtained by heating (3) to (8) of (A) in Table 5 to 80 ° C. and stirring to homogenize the solution, which was previously dissolved in (10) while stirring (1), is heated to 80 ° C. Then, after adding with stirring, (9) was added with cooling and uniformly mixed.
In this way, the rinses having the compositions shown in (A) of Table 5 were adjusted, and the formulations of the invention products 9 to 16 were obtained in the order of the invention products obtained in Examples 1 to 8. As a standard product, the standard product (B) in Table 5
A rinse was prepared in which the amino acid-modified cationic polymer shown in 1 above was not mixed. To the solution obtained by heating (3) to (8) of (B) in Table 5 to 80 ° C. and stirring to homogenize, add (10) heated to 80 ° C. with stirring and then cooling ( 9) was added and mixed uniformly. In this way, (B) in Table 5
The rinse having the composition shown in was adjusted to be a standard product.

[0071]

[Table 5]

With respect to each rinse prepared in (A) of Table 5, the performance evaluation of the following items was carried out by 10 testers. The flexibility of dry hair, combing, squeaky feeling, moisturizing feeling, dry feeling, and barbs were compared with the standard product prepared in the standard product (B) of Table 5, and the values were quantified by the method of Table 6 below. The integrated value was calculated. The evaluation results are shown in Table 7.

[0073]

[Table 6]

Comparative Example 3 In order to compare the effect with the amino acid-modified cationized polymer used in the present invention, cation-modified hydroxyethyl cellulose having an ethylene oxide average addition mole number of 1.8 and a nitrogen content of 1.8% by weight was used. A rinse having the composition shown in the comparative product (C) was prepared. (3) of (C) in Table 5
~ (8) was heated to 80 ℃, stirred to a uniform solution,
8 solution prepared by dissolving (2) in (10) while stirring.
After heating to 0 ° C. and adding with stirring, (9) was added with cooling and uniformly mixed. Thus, (C) in Table 5
The rinse having the composition shown in was adjusted to obtain Comparative product 5. In the same manner as in Example 10, the flexibility of dry hair after combing, combing, creaking, moisturizing, dryness and luster were compared with the standard product. The results are shown in Table 7.

Comparative Example 4 Similar to the rinse formulation of Comparative Example 3, two formulations of diallyldimethylammonium chloride / acrylamide copolymer and N- [3-alkyloxy-2-hydroxypropyl] -L-arginine were combined. (Comparative product 6,
7) Evaluation was performed. The results are shown in Table 7.

[0076]

[Table 7]

From the results shown in Table 7, it can be seen that the rinse performance was improved by the amino acid-modified cationized polymer which is a neutralized product of the organic acid and / or inorganic acid of the amino acid-modified water-soluble polymer.

Further, it was found that the amino acid-modified cationized polymer of the present invention was superior to the cation-modified hydroxyethyl cellulose in combing, was soft and had less sticky feeling, and gave a dry feel. Further, it was found that it was excellent in combing and gave a moist feel when compared with a diallyldimethylammonium chloride / acrylamide copolymer. It was found to give a smooth and dry feel when compared to N- [3-alkyloxy-2-hydroxypropyl] -L-arginine.

Example 11 A body soap having the composition shown in (A) of Table 8 was prepared using the amino acid-modified cationized polymers obtained in Examples 1-8. (11) of (A) in Table 8 is heated to 60 ° C.,
After adding (1) with stirring to dissolve and confirming dissolution, (3) to (7) were added with stirring at 50 to 60 ° C. to homogenize, and (8) to (10) at 30 to 40 ° C. ) Was similarly added with stirring and mixed uniformly. In this way, body soaps having the compositions shown in (A) of Table 8 were adjusted, respectively, and the formulations 17 to 2 of the invention products were obtained in the order of the invention products obtained in Examples 1 to 8.
It was set to 4. As a standard product, a body soap containing no amino acid-modified cationic polymer shown in the standard product (B) of Table 8 was prepared. (B) (11) in Table 8 at 60 ° C
The mixture is heated to 50 ° C to 60 ° C and (3) to (7) is added with stirring to make the mixture uniform, and further at 30 to 40 ° C, (8) to (1).
0) was similarly added with stirring and mixed uniformly. In this way, the body soap having the composition shown in (B) of Table 8 was adjusted,
Standard product.

[0080]

[Table 8]

With respect to each body soap adjusted in (A) of Table 8, the performance evaluation of the items shown below was carried out by 10 testers. The amount and quality of foam during use, ease of rinsing, tightness and sliminess after rinsing, tightness after drying, stickiness, and moistness are the standard products adjusted with the standard product (B) in Table 8. For comparison, Table 9 and Table 1 below
The value was converted into a numerical value by the method of 0 and the integrated value was obtained. The evaluation results are shown in Table 11.

Comparative Example 5 In order to compare the effect with the amino acid-modified cationized polymer used in the present invention, cation-modified hydroxyethyl cellulose having an average addition mole number of ethylene oxide of 1.8 and a nitrogen content of 1.8% by weight was used. A body soap having the composition shown in the comparative product (C) was prepared. (11) of (C) in Table 8 was heated to 60 ° C., (2) was added while stirring to dissolve, and after confirming dissolution, (3) at 50 to 60 ° C.
(7) is added with stirring to make it uniform, and further 30-40
(8) to (10) were similarly added with stirring at 0 ° C. and mixed uniformly. In this way, the body soap having the composition shown in (C) of Table 8 was prepared and designated as Comparative product 8. Similar to Example 11, the amount and quality of bubbles during use, ease of rinsing, tightness and sliminess after rinsing, tightness after drying, stickiness and moistness were compared with the standard product. The results are shown in Table 1.
Shown in 1.

[0083]

[Table 9]

[0084]

[Table 10]

COMPARATIVE EXAMPLE 6 Similar to the body soap formulation of Comparative Example 5, a diallyldimethylammonium chloride / acrylamide copolymer was formulated and Comparative Product 9 was evaluated. The results are shown in Table 11.

[0086]

[Table 11]

From the results shown in Table 11, it can be seen that the performance of the body soap is improved by the amino acid-modified cationized polymer which is a neutralized product of the organic acid and / or inorganic acid of the amino acid-modified water-soluble polymer.

Further, it was found that the amino acid-modified cationized polymer of the present invention has less slimy feeling after rinsing than cation-modified hydroxyethyl cellulose, reduces the tense feeling after drying, and gives a dry feel without stickiness. It was Further, it was found that compared to the diallyldimethylammonium chloride / acrylamide copolymer, the feeling of tightness was improved, and a dry feel was imparted without stickiness.

[0089]

EFFECT OF THE INVENTION The amino acid-modified water-soluble polymer of the present invention is neutralized with an acid, and the amino acid-modified cationized polymer is incorporated into hair cosmetics such as shampoos and conditioners to give the amino acid derivative a suitable adsorption action on hair. It has a long-lasting effect and does not fall off during rinsing. It also improves the sticky feeling and dryness of conventional cationic polymers, gives a smooth finger passage during rinsing, and gives a soft and silky finish after drying. When added to skin cosmetics such as body soap, it gives a dry feel without a tightness.

Front page continuation (51) Int.Cl. ⁷ Identification code FI theme code (reference) C08F 16/14 C08F 16/14 20/36 20/36 F term (reference) 4C083 AB052 AC072 AC122 AC182 AC302 AC312 AC342 AC392 AC482 AC532 AC642 AC712 AC782 AC902 AD091 AD092 AD111 AD112 BB34 CC23 CC38 CC39 DD23 DD27 EE06 4J100 AD02Q AD03Q AE18P AE18Q AG04Q AJ01Q AJ02Q AL03Q AL08Q AL09Q AL10P AL10Q AM15Q AM21Q AQ08Q BA03Q BA06Q BA08Q BA12Q BA16H BA27H BA30H BA56Q BA64Q BC54P BC54Q CA04 HA61 HC28 HC46 HE13 JA61

Claims (8)

[Claims] 1. An amino acid-modified cationized polymer obtained by neutralizing a water-soluble polymer having an amino acid as a side chain with an acid. 2. A polymer of an oxirane compound having a water-soluble polymer having an amino acid as a side chain and having an ethylenic double bond represented by the following chemical formula (1) and / or an allyl represented by the following chemical formula (2). A reaction product of a polymer of an oxirane compound having a polymerizable double bond and an amino acid.
The amino acid-modified cationized polymer described. (In the formula, R ₁ is hydrogen, an alkyl group having 1 to 3 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, R ₂ is hydrogen, a carboxymethyl group or an alkyl group having 1 to 3 carbon atoms, R ₃ , R ₄
And R ₅ each represent hydrogen or an alkyl group having 1 to 3 carbon atoms) (In the formula, R ₁ is hydrogen, an alkyl group having 1 to 3 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, R ₂ is hydrogen, a carboxymethyl group or an alkyl group having 1 to 3 carbon atoms, R ₃ , R ₄
And R ₅ each represent hydrogen or an alkyl group having 1 to 3 carbon atoms) 3. A water-soluble polymer having an amino acid as a side chain, an oxirane compound represented by the chemical formula (1) and / or the chemical formula (2) of claim 2, and a single monomer having an ethylenic and allylic double bond. The amino acid-modified cationized polymer according to claim 1, which is a reaction product of an amino acid with a copolymer of one kind of monomer selected from a monomer. 4. The amino acid-modified cationization according to claim 1, 2 or 3, wherein the oxirane compound having an ethylenic double bond represented by the chemical formula (1) in claim 2 is glycidyl acrylate and / or glycidyl methacrylate. polymer. 5. The amino acid according to claim 1, 2 or 3, wherein the oxirane compound having an allylic double bond represented by the chemical formula (2) in claim 2 is allyl glycidyl ether and / or methallyl glycidyl ether. Modified cationized polymer. 6. The amino acid-modified cationized polymer according to claim 1, wherein the side chain amino acid is a basic amino acid. 7. The acid for neutralizing a water-soluble polymer having an amino acid as a side chain is an organic acid and / or an inorganic acid.
~ 6 amino acid modified cationized polymer. 8. A cosmetic composition comprising the amino acid-modified cationized polymer according to claim 1 as an active ingredient.