JP3446979B2 - Water-soluble hairdressing - Google Patents

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a water-soluble hair styling agent such as hair liquid, set lotion, hair styling gel, water grease, hair styling mousse agent, hair styling blow agent, and more specifically, for protecting hair. Restores damaged hair, shines and moisturizes hair,
The present invention relates to a water-soluble hair styling agent which imparts a tension (tension), prevents split ends, improves combability of hair, and has excellent storage stability.

[0002]

2. Description of the Related Art Heretofore, as a hair styling agent, oily hair styling agents such as pomade and hair oil, which impart tackiness and luster to the hair by using vegetable oils and mineral oils as the main ingredients, have been used recently. Water-soluble hair styling products such as hair liquids, set lotions, hair styling gels, and hair styling mousses, which have little thickness, have been mainly used.

[0003] In these water-soluble hair styling agents, a water-soluble polymer setting agent is blended to give the hair a setting power and luster. Further, from the pursuit of a more natural hair luster, it has been attempted to add silicone or protein hydrolyzate to these water-soluble hair styling agents like other cosmetics.

[0004]

However, since silicone is generally a hydrophobic substance, there is a problem that it is difficult to incorporate it in a water-soluble hair styling composition, except for a small amount of modified silicone. Silicone is easily sorbed to hair with little damage, that is, highly hydrophobic hair, but to damaged hair, that is, hair that becomes hydrophilic due to exposure of hydrophilic groups to the surface. It is said that it is difficult to sorb, and there is a problem that the characteristics possessed by silicone cannot be sufficiently exerted on damaged hair.

The protein hydrolyzate is very useful for recovering hair damaged by elution of protein components in the hair by washing the hair, etc., but the protein hydrolyzate is generally a water-soluble substance. However, even water-soluble hair styling products often contain oils and fats and alcohols, and there is a problem that the amount of protein hydrolyzate to be mixed is limited and that protein hydrolyzate coagulates and precipitates during storage. there were.

Therefore, the present invention protects the hair, restores the damaged hair, imparts gloss, moisturizing and balding to the hair, prevents split ends, improves the combability of the hair, and is storage-stable. An object is to provide a water-soluble hair styling agent having excellent properties.

[0007]

Means for Solving the Problems As a result of intensive studies to achieve the above object, the present inventors have found that a functional group containing only one silicon atom in the amino group of a peptide containing the amino group of the amino acid side chain. The following general formula (I) in which (silyl functional group) is covalently bonded

[0008]

[Chemical 3]

[In the formula, at least two of R ¹ , R ² and R ³ represent a hydroxyl group, and the rest represent a methyl group. R ⁴ represents a residue excluding the terminal amino group of a basic amino acid having an amino group at the end of the side chain, R ⁵ represents a side chain of an amino acid other than R ⁴ , a is 1 or 3, and m is 0. Greater than 50
Hereinafter, n is 1 to 200, m + n is 2 to 200 (however, m and n only indicate the number of amino acids, not the order of the amino acid sequence)], or , The following general formula (II)

[0010]

[Chemical 4]

[In the formula, ^{two of} R ¹ , R ² and R ³ represent a hydroxyl group, and the rest represent a methyl group. R ⁴ represents a residue excluding the terminal amino group of a basic amino acid having an amino group at the end of the side chain, R ⁵ represents a side chain of an amino acid other than R ⁴ , a is 1 or 3, and m is 0. Greater than 50 or less, n
Is 1 to 200 and m + n is 2 to 200 (however, m
And n only show the number of amino acids, not the order of amino acid sequences)], the silylated peptide has both the properties of the peptide and the properties of the silicone. When the silylated peptide is added to a water-soluble hair styling composition containing a water-soluble polymer setting agent, it protects the hair, restores damaged hair, imparts gloss, moisturizing and softness to the hair, and splits the hair. The inventors have found that a water-soluble hair styling product that can prevent the hair, improve the combability of hair, and have excellent storage stability can be obtained, and completed the present invention.

That is, the silylated peptide sorbs to the hair by the sorption action of the peptide moiety, protects the hair, restores damaged hair, and moisturizes the hair.
The silyl functional group part also sorbs to the hair via the peptide part, so it smoothes the surface of the hair, imparts gloss and luster to the hair, improves combability of the hair, and causes split ends by combing. Prevent. Moreover, since the silylated peptide has water solubility, it has excellent storage stability in a water-soluble hair styling material.

The water-soluble hair styling agent of the present invention is prepared by using the water-soluble polymer setting agent and the silylated peptide as an essential component. First, the silylated peptide will be described in detail below.

[Silylated Peptide] The silylated peptide represented by the above general formula (I) is, for example, the following general formula (III)

[0015]

[Chemical 5]

[Wherein R ⁶ , R ⁷ , and R ⁸ represent a methyl group, an alkoxy group having 1 to 3 carbon atoms, a hydroxyl group, or a halogen atom, and R ⁶ , R ⁷ , and R ⁸ may be the same. Also, two or more of R ⁶ , R ⁷ and R ⁸ may not be methyl groups at the same time, although they may be different. a is 1 or 3, and X is a halogen atom such as Cl, Br, F, or I], and the following general formula (IV)

[0017]

[Chemical 6]

[In the formula, R ⁴ represents a residue excluding an amino group of a basic amino acid having an amino group at the end of a side chain, and R ⁵
Is an amino acid side chain other than R ⁴ , and m is greater than 0 and 5
0 or less, n is 1 to 200, and m + n is 2 to 200]
It can be obtained by a condensation reaction with the peptides represented by

The silylated peptide represented by the general formula (II) is, for example, the following general formula (V)

[0020]

[Chemical 7]

[In the formula, one of R ⁶ , R ⁷ and R ⁸ represents a methyl group, and the remaining two represent an alkoxy group having 1 to 3 carbon atoms, a hydroxyl group or a halogen atom. a represents 1 or 3] and a silyl compound represented by the general formula (IV) are subjected to a condensation reaction.

[Characteristics of Silylated Peptide] The silylated peptide represented by the general formula (I) and the general formula (I
As is clear from the chemical structural formula, the silylated peptide represented by I) is a silicon atom based on the silyl compound represented by the general formula (III) or the silyl compound represented by the general formula (V). Since it has a silyl functional group moiety containing a and a peptide moiety based on the peptides represented by the general formula (IV), when it is incorporated into a water-soluble hair styling product, the silyl functional group moiety has excellent extensibility and friction reduction. Properties, gloss and luster, water repellency, etc., and sorption of peptide part to hair, resulting in volume increase of hair, firmness, protection by film formation, moisturizing, etc. Can be demonstrated. Moreover, since peptides have a good sorption property to damaged hair, the silylated peptide can sorb a silyl functional group via a peptide moiety to damaged hair that is difficult to sorb with a high molecular weight silicone oil. Therefore, it is possible to improve the feel of damaged hair and contribute to the recovery of strength.

Therefore, when this silylated peptide is blended to prepare a water-soluble hair styling product, the silylated peptide prevents damage to the hair, imparts luster and moisture to the hair, smoothes the hair, and Improves combability, split ends,
Prevents the generation of cut hair and restores damaged hair.

Also, high molecular weight silicone is difficult to remove once it adheres to the hair, and therefore, perm, bleach,
Although it has the drawback of making chemical treatment such as hair dyeing difficult and reducing the sorption action of peptides and cationic polymers on hair, the silylated peptide represented by the above general formula (I) and the general formula The silylated peptide represented by (II) has a low-molecular-weight silyl functional group bound to the peptide part, and it sorbs to the hair by a normal peptide sorption mechanism. By washing with the agent, the silylated peptide can be reversibly desorbed from the hair and the above-mentioned adverse effects do not occur.

In the silylated peptide represented by the general formula (I), at least two of R ¹ , R ² and R ³ are hydroxyl groups, and the rest are methyl groups. In the silylated peptide according to the present invention, ^{two of} R ¹ , R ² and R ³ are hydroxyl groups and the rest are methyl groups, which means that the silylated peptide represented by the general formula (I) or the general formula ( This is because the silylated peptide represented by II) has water solubility and maintains good storage stability in a water-soluble hairdressing preparation. Further, a is specified as 1 or 3 when a is 2, the storage stability in the state of the silyl compound represented by the general formula (III) or the silyl compound represented by the general formula (V). This is because if the property is poor and a is larger than 3, the proportion of the silyl functional group portion in the entire molecule becomes small, and the characteristics of the silyl functional group cannot be fully exhibited.

[Peptide Part in Silylated Peptide] The silylated peptide represented by the general formula (I) or the general formula (I
In the silylated peptide represented by I), R ⁴ is a residue excluding the terminal amino group of a basic amino acid having an amino group at the end of the side chain. Examples of the basic amino acid possessed include lysine, arginine, hydroxylysine and the like.
R ⁵ represents a side chain of an amino acid other than R ⁴ , and examples of such an amino acid include glutamic acid, aspartic acid, alanine, serine, threonine, valine,
Methionine, leucine, isoleucine, tyrosine, phenylalanine, proline, hydroxyproline and the like can be mentioned.

In the silylated peptide represented by the general formula (I) or the silylated peptide represented by the general formula (II),
m is greater than 0 and 50 or less (0 <m ≦ 50),
It is preferably more than 0 and 10 or less (0 <m ≦ 10), n is 1 to 200, and preferably 1 to 100,
More preferably 2-40, m + n is 2-200, preferably 2-100, more preferably 3-5.
Although it is 0, this is due to the following reason.

That is, when m is larger than the above range, the number of silyl functional groups bonded to the amino group of the side chain is increased, and the sorption action on the original hair of the peptide is decreased. The ratio of the silyl functional group portion to the silyl functional group portion is reduced, and the effect of the silyl functional group portion cannot be fully exerted. When m + n is larger than the above range, the peptide has poor sorption and penetrability on hair. In addition to the decrease in molecular weight of the peptide, it tends to aggregate during storage, resulting in poor storage stability.

The above m, n and m + n are theoretically integers, but when the peptide portion is a hydrolyzed protein as described below, the hydrolyzed protein is obtained as a mixture of those having different molecular weights. Therefore, the measured value becomes an average value.

The peptides represented by the above general formula (IV) include peptides or esters of peptides.

The above peptides include natural peptides, synthetic peptides, hydrolyzed peptides obtained by partially hydrolyzing a protein (protein) with an acid, an alkali or an enzyme.

Examples of natural peptides include glutathione, bacitracin A, insulin, glucagon, oxytocin, vasopressin, etc., and examples of synthetic peptides include polyglycine, polylysine, polyglutamic acid, polyserine and the like.

Examples of the hydrolyzed peptide include collagen (including its modified product gelatin), keratin, silk fibroin, sericin, casein, conchiolin, elastin, chicken, and egg yolk protein of eggs such as duck,
Proteins derived from plants and animals such as egg white protein, soy protein, wheat protein, corn protein, rice (rice bran) protein, potato protein, or yeasts of the genera Saccharomyces, Candita and Endomycopsis, so-called beer yeast, sake yeast. Peptides obtained by partially hydrolyzing microorganism-derived proteins such as yeast proteins isolated from yeasts, proteins extracted from mushrooms (basidiomycetes), proteins isolated from Chlorella with acid, alkali or enzyme And so on.

Examples of the ester of the above peptide include esters with a hydrocarbon alcohol having 1 to 20 carbon atoms in the carboxyl group of the above peptide, for example, methyl ester, ethyl ester, propyl ester, isopropyl ester, lauryl ester, cetyl ester, 2 -Ethylhexyl ester, 2-hexyldecyl ester,
Stearyl ester etc. are mentioned.

[Synthesis of Silylated Peptide] The silylated peptide represented by the general formula (I) or the silylated peptide represented by the general formula (II) can be prepared by using the general formula (II
The silyl compound represented by I) or the silyl compound represented by the general formula (V) and the peptide represented by the general formula (IV) are subjected to a catalytic reaction to obtain a compound represented by the general formula (III As the silyl compound represented by) and the silyl compound represented by the general formula (V), commercially available silane coupling agents can be used. Examples of such a silane coupling agent include T, manufactured by Toshiba Silicone Co., Ltd.
SL8390, TSL8219, TSL8395, TS
L8326, TSL8325, TSL8320, TSL
8355, TSL8350 (both are trade names), Nippon Unicar Co., Ltd. A-143 (trade name), Toray Dow Corning Silicone Co., Ltd. SH6040, SH
6076 (both are trade names), Shin-Etsu Silicone Co., Ltd.
KBM403, KBM402, KBM703 (all are trade names) manufactured by K.K.

The silyl compound represented by the general formula (III) or the silyl compound represented by the general formula (V) and the general formula (IV)
In the reaction with the peptides represented by, for example, first, the silyl compound is stirred in water at 30 to 50 ° C. for 5 to 20 minutes to be hydrolyzed, whereby an alkoxy group or a halogen atom bonded to a silicon atom is converted into a hydroxyl group. After conversion into, the hydroxylated silyl compound is added dropwise to the solution of the peptide represented by the general formula (IV), and both are brought into contact with each other.

In the above reaction, the peptides were 30 to 5
The aqueous solution is preferably about 0% by weight, and the dropping of the hydroxylated silyl compound is preferably completed in 30 minutes to 5 hours.

When the silyl compound represented by the general formula (III) is used, during the reaction, hydrogen halide is produced by the reaction and the pH of the reaction solution is lowered. It is preferable to maintain the pH in the reaction system at 8 to 11, particularly 9 to 10, by dropping an alkaline solution such as. Further, when the silyl compound represented by the general formula (V) is used, the pH does not decrease due to the reaction, but the reaction proceeds on the basic side, so the pH of the peptide solution is 8 to 11, particularly 9 to 10. It is preferable to keep it at 10.

The reaction proceeds even at room temperature, but the higher the temperature, the faster the reaction rate. However, since the hydrolysis of the silyl compound is promoted when the temperature rises in a high pH state, it is preferably at most 70 ° C. or lower, and particularly preferably 40 to 60 ° C.

The progress and completion of the reaction can be confirmed by measuring the amount of amino nitrogen of the peptides in the reaction by the Van Slyke method.

After completion of the reaction, the reaction solution is neutralized, then appropriately concentrated, and purified by ion exchange resin, dialysis membrane, electrodialysis, gel filtration, ultrafiltration, etc. Used for the preparation of hair styling products.

In the silylated peptide represented by the above general formula (I), the introduction rate of the silyl functional group (that is, the functional group containing only one silicon atom) into the amino group of the peptide is 50% or more and 85% or less. Is preferred. If the introduction rate of the silyl functional group is less than 50%, the characteristics based on the silyl compound may not be sufficiently exhibited, and if it is more than 85%, the hydrophobicity may increase and the hydrophilicity may decrease.

In the silylated peptide represented by the general formula (II), the introduction rate of the silyl functional group into the amino group of the peptide is preferably 50% or more and 75% or less. If the introduction rate of the silyl functional group is less than 50%, the characteristics based on the silyl compound may not be sufficiently exhibited.
If it exceeds 5%, the hydrophobicity may increase and the hydrophilicity may decrease.

[Amount of Silylated Peptide] The amount of the silylated peptide represented by the general formula (I) or the silylated peptide represented by the general formula (II) to the water-soluble hair styling agent (water-soluble hair styling agent) Content) in 0.1
-20 wt% is preferable, and 0.5-15 wt% is particularly preferable. That is, when the amount of the silylated peptide added to the water-soluble hair styling agent is less than the above range, the effects of imparting luster and moisture to the hair, protecting the hair, and improving combability are sufficiently exhibited. Moreover, even if the amount of the silylated peptide to be added to the water-soluble hair styling agent exceeds the above range, almost no increase in the effect due to the increase in the amount of addition is observed, and the stickiness caused by the peptide portion is not observed. It will occur. In addition, the above silylated peptides may be used alone or in combination of two or more when blending with the water-soluble hair styling agent.

[Water-Soluble Polymer Setting Agent] The water-soluble polymer setting agent is not particularly limited, and any of natural setting agents, semi-synthetic setting agents, and synthetic setting agents can be used as in the past. . Examples of the natural and semi-synthetic water-soluble polymer setting agents include ethyl cellulose, hydroxyethyl cellulose, sodium carboxymethyl cellulose, natural protein hydrolysates or quaternized derivatives thereof. Further, as the synthetic water-soluble polymer setting agent, for example, polyvinylpyrrolidone, vinylpyrrolidone-alkylaminoacrylate copolymer, polyvinylpyrrolidone-vinyl acetate copolymer, carboxyvinyl polymer, polyacrylic acid ester, polymethacrylic acid ester , A copolymer of acrylic acid and / or methacrylic acid with an acrylic acid alkyl ester and / or a methacrylic acid alkyl ester.

The content of this water-soluble polymer setting agent in the water-soluble hair styling agent is 0.1 to 10% by weight, particularly 0.5.
-5% by weight is preferred. That is, when the content of the water-soluble polymer setting agent in the water-soluble hair styling agent is less than the above range, the effect of setting hair is not sufficiently exerted, and the content of the water-soluble polymer setting agent in the water-soluble hair styling agent is insufficient. When the content is more than the above range, the hair may be hardened, and the natural product type setting agent may have high hygroscopicity and become sticky, or the set holding power may be lowered.

[Preparation of Water-Soluble Hairdressing Agent Containing Silylated Peptide] The water-soluble hairdressing agent of the present invention is intended for hair liquid, set lotion, hair styling gel, hair styling mousse agent, hair styling blow agent, water grease, etc. , A water-soluble polymer setting agent, and the like, which are usually added to those water-soluble hair styling agents, and then the silylated peptide is added. However, the order of compounding may be either first,
For example, containing a water-soluble polymer setting agent, hair liquid, set lotion, hair styling gel, hair styling mousse agent, hair styling blow agent,
The silylated peptide may be blended with a pre-prepared product such as water grease, and the silylated peptide may be blended with the water-soluble polymer setting agent and other components when preparing the water-soluble hair styling product. May be.

The above silylated peptides can be used in combination with various other components in addition to the water-soluble polymer setting agent, and in each water-soluble hair styling agent, they are appropriately used in combination with other components. .

Examples of such components include ammonium lauryl sulfate, ethanolamine lauryl sulfate,
Alkylsulfates such as sodium lauryl sulfate and triethanolamine lauryl sulfate, polyoxyethylene (2
EO) lauryl ether sulfate triethanolamine (where EO is ethylene oxide, the number before EO indicates the number of moles of ethylene oxide added), polyoxyethylene (3EO) alkyl (any of 11 to 15 carbon atoms or Mixture of two or more kinds) Polyoxyethylene alkyl ether sulfate such as sodium ether sulfate, sodium lauryl benzene sulfonate, alkyl benzene sulfonate such as triethanolamine lauryl benzene sulfonate, sodium polyoxyethylene (3EO) tridecyl ether acetate Polyoxyethylene alkyl ether acetate, such as coconut oil fatty acid sarconsi sodium, lauroyl sarcosine triethanolamine,
Lauroylmethyl-β-alanine sodium, sodium lauroyl-L-glutamate, lauroyl-L-glutamate triethanolamine, coconut oil fatty acid-L-
N-acyl amino acid salts such as sodium glutamate, coconut oil fatty acid-L-glutamic acid triethanolamine, coconut oil fatty acid sodium methyl taurate, sodium lauroyl methyl taurine, sodium ether alkanesulfonate, hardened coconut oil fatty acid glycerin sodium sulfate, undecyl Noylamide ethyl disodium sulfosuccinate, sodium octylphenoxydiethoxyethyl sulfonate, oleic acid amide disodium sulfosuccinate, dioctyl sodium sulfosuccinate, disodium lauryl sulfosuccinate, polyoxyethylene alkyl (carbon number 12-16) ether phosphate (2-12EO), sodium polyoxyethylene oleyl ether phosphate, sodium polyoxyethylene cetyl ether phosphate Polyoxyethylene sulfo lauryl disodium succinate, sodium polyoxyethylene lauryl ether phosphate, sodium lauryl sulfoacetate, sodium tetradecene sulfonate, collagen, keratin, fibroin, casein, soy, wheat,
An acylated hydrolyzed protein obtained by acylating a protein hydrolyzate derived from plants and animals such as corn, potatoes, yeasts, etc. with a fatty acid having 8 to 20 carbon atoms, or anions such as salts thereof such as sodium, potassium and triethanolamine. Surfactant, 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, undecylhydroxyethylimidazolium betaine sodium, undecyl-N-hydroxyethyl-N-carboxymethylimidazolinium betaine, stearyldihydroxy Ethyl betaine, stearyl dimethylaminoacetic acid betaine, coconut oil alkyl betaine, coconut oil fatty acid amide propyl betaine, coconut oil alkyl-
N-carboxyethyl-N-hydroxyethyl imidazolinium betaine sodium, coconut oil alkyl-N-carboxyethoxyethyl-N-carboxyethyl imidazolinium disodium hydroxide, coconut oil alkyl-N-carboxymethoxyethyl-N-carboxy Amphoteric surfactants such as methyl imidazolinium disodium lauryl sulfate, N-coconut oil fatty acid acyl-L-arginine ethyl DL-pyrrolidone carboxylate, polyoxyethylene alkyl (C12-14) ether (7E
O), polyoxyethylene octyl phenyl ether, polyoxyethylene oleyl ether, polyoxyethylene glyceryl oleate, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene cetyl stearyl diether, polyoxyethylene sorbitol lanolin ( 40EO), polyoxyethylene nonylphenyl ether, polyoxyethylene polyoxypropylene cetyl ether, polyoxyethylene polyoxypropylene decyl tetradecyl ether, polyoxyethylene lanolin, polyoxyethylene lanolin alcohol, polyoxypropylene stearyl ether, alkyl glycoside, Nonionic surfactants such as alkyl polyglycosides, stearyl trimethylammonium chloride System, cetyltrimethylammonium chloride, cetostearyltrimethylammonium chloride, stearylbis (diethyleneglycol) hydroxyethylammonium chloride, behenyltrimethylammonium chloride, distearyldimethylammonium bromide, tri [polyoxyethylene (5EO)] stearylammonium chloride, stearyl chloride. Dimethylbenzylammonium, behenyltrimethylammonium bromide, cetyltrimethylammonium iodide, oleylbenzyldimethylammonium chloride, oleylbis [polyoxyethylene (15EO)] methylammonium chloride, alkyltrimethylammonium salt, dialkyldimethylammonium salt, polyoxypropylenemethyl chloride. Diethyl ammonium, Mink chloride oil Fatty acid amide Pyrdimethylhydroxyethylammonium, γ-gluconamide propyldimethylhydroxyammonium chloride, cationic surfactants such as alkylpyridinium salts, isostearic acid diethanolamide, undecylenic acid monoethanolamide, oleic acid diethanolamide, tallow fatty acid monoethanolamide, hardening Beef tallow fatty acid diethanolamide, stearic acid diethanolamide, stearic acid diethylaminoethylamide, stearic acid monoethanolamide, myristic acid diethanolamide, coconut oil fatty acid ethanolamide, coconut oil fatty acid diethanolamide, lauric acid isopropanolamide, lauric acid ethanolamide, laurin Acid diethanolamide,
Thickeners such as lanolin fatty acid diethanolamide, waxes, paraffins, fatty acid esters, glycerides, oils and fats such as animal and vegetable oils, animal and vegetable extracts, collagen, keratin, fibroin, sericin, casein, soybean, wheat, corn, potato, rice ( Rice bran), yeast, hydrolyzed peptides of proteins derived from animals and plants such as mushrooms and microorganisms and peptide ester derivatives thereof, propylene glycol, 1,3-butylene glycol, ethylene glycol, glycerin, polyethylene glycol and other wetting agents, ethanol, Lower alcohols such as methanol, propyl alcohol and isopropyl alcohol, higher alcohols such as cetyl alcohol, stearyl alcohol, oleyl alcohol and behenyl alcohol, L-aspara Phosphate, sodium L- aspartate, DL-alanine, L- arginine, glycine, L
-Amino acids such as glutamic acid, L-cysteine and L-threonine can be mentioned.

Further, chain or cyclic methyl polysiloxane, methylphenyl polysiloxane, dimethyl polysiloxane polyethylene glycol copolymer, dimethyl polysiloxane polypropylene copolymer, amino-modified silicone, quaternary ammonium-modified silicone, and other silicones are used. When used in combination, since the silyl functional group portion of the silylated peptide is compatible with silicone, the emulsion stabilizer of silicone in the water-soluble hair styling agent is increased, so that the action of silicone is easily exhibited.

[0051]

The water-soluble hair styling composition of the present invention protects hair, restores damaged hair, and imparts gloss, luster and moisturizing to the hair. In particular, the silylated peptide sorbs silyl functional groups to the hair via the peptide moiety, which gives the hair luster and moisture, improves the combability of the hair, and prevents split ends from combing. To do. Further, in the water-soluble hair styling composition of the present invention, the silylated peptide is water-soluble, and therefore the storage stability is excellent.

[0052]

EXAMPLES Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples. In addition, the blending amount of each component in Examples and Comparative Examples is based on parts by weight, and when the blending amount is not the solid content, the solid content concentration is shown in parentheses after the component name. Further, in the examples and the like,% indicating the concentration is% by weight.

Example 1 and Comparative Examples 1 and 2 Three kinds of set lotions having the compositions shown in Table 1 were prepared,
Each set lotion was applied to shampoo-washed hair to study the gloss, moisturization and set retention of the treated hair.

The usage of the silylated peptide in the set lotions of Example 1 and Comparative Examples 1 and 2 will be described. In Example 1, the silylated peptide represented by the general formula (I) is R ¹ ═CH ₃ , R ²
= OH, R ³ = OH, a = 3, the average value of m = 2, the average value of n = 8, the average value of m + n = 10, and the silylated hydrolyzed keratin having a silyl functional group introduction rate of 61% is obtained. I am using. In Comparative Example 1, methylphenyl polysiloxane [SH556 manufactured by Toray Dow Corning Silicone Co., Ltd. was used as the silicone instead of the silylated hydrolyzed keratin.
(Trade name)], and in Comparative Example 2, neither silylated peptide nor silicone is used.

[0055]

[Table 1]

Prior to the treatment with the above set lotion, the hair was previously treated with 2% polyoxyethylene (10E).
O) Washed with nonyl phenyl ether aqueous solution, rinsed with water and air dried in greenhouse. Select 20 hairs from this hair,
Twenty of them are bundled, the hair roots are aligned and fixed with an adhesive, the length is aligned to 18 cm, the diameter is 10 mm and the length is 80 m.
It was wound around a rod of m and fixed at both ends with rubber bands. Each of the rods was dipped in the set lotion of Example 1 and Comparative Examples 1 and 2 for 10 seconds. After the dipping, excess set lotion was sucked with a towel, and then the hair bundle was air-dried at room temperature for 12 hours while being wound around the rod. .

After drying, the hair bundle was detached from the rod and suspended with the hair root side up, and the length of the hair bundle at this time was measured and taken as the length at 0 hour (L ₀ ). Next, this hair bundle was left suspended in a 58% constant humidity tank for 20 hours, the length of the hair bundle was measured, and this was taken as L _20, and the set retention rate was calculated by the following formula. The results are shown in Table 2.

[0058]

Before measuring the set retention rate, 10 female panelists evaluated the luster and moisturization of the hair when these hair bundles were removed from the rod.

As for the evaluation criteria, the best one is [2 points], the second best one is [1 point], and the worst one is [0].
Point], the results are shown in Table 2 as an average value of 5 persons.

[0061]

[Table 2]

As shown in Table 2, the set lotion of Example 1 has a larger amount than the set lotion of Comparative Examples 1 and 2.
It was revealed that the evaluation values of gloss and moisturization of hair are high, and that the silylated peptide is well sorbed on the hair to impart gloss and moisturization to the hair. In addition, the set retention rate of Example 1 is
Although it was slightly better than Comparative Example 2 in which the silylated peptide or silicone was not added, in Comparative Example 1 in which silicone was added, the set retention rate was lowered due to the influence of silicone, whereas the set of Example 1 was set. Since the retention rate was equal to or higher than that of Comparative Example 2, it was revealed that the silylated peptide does not interfere with the action of the setting agent.

Example 2 and Comparative Examples 3 to 4 Three types of hair styling gels having the compositions shown in Table 3 were prepared, and the gloss, moisturization and set retention rate of the hair when each of the hair styling gels was used were evaluated. It investigated like 1.

In Example 2, as the silylated peptide, R ¹ ═CH ₃ and R ² ═O in the general formula (II) were used.
H, R ³ = OH, a = 3, average value of m = 1.4, average value of n = 18.6, average value of m + n = 20, and silyl functional group having a silyl functional group introduction rate of 67%. Degraded collagen is used. In Comparative Example 3, instead of the silylated hydrolyzed collagen, a water-soluble dimethylsiloxane / methyl (polyoxyethylene) siloxane copolymer [SH-377 manufactured by Toray Dow Corning Silicone Co., Ltd. was used.
1C (trade name)], and in Comparative Example 4, neither silylated peptide nor silicone was used.

[0065]

[Table 3]

Prior to the treatment with the above hair styling gel, the hair was treated in the same manner as in Example 1. However,
Since these hair styling gels are gel type, they are treated in the hair bundle in Example 2 and Comparative Example 3 to
0.2 g of each of the hair styling gels of Example 4 was applied to the hair wrapped around the rod while being well spread. 10 female panelists evaluated the luster and moisture of the hair immediately after removing it from the rod according to the same evaluation criteria as in Example 1,
The set retention rate was also examined in the same manner as in Example 1. Table 4 shows the results.

[0067]

[Table 4]

As shown in Table 4, the hair styling gels of Example 2 had higher evaluation values for both gloss and moisturization of the hair than the hair styling gels of Comparative Examples 3-4.
It was revealed that the set retention rate was also good, and that the silylated hydrolyzed collagen sorbed to the hair to give the hair gloss and moisturizing and not to hinder the styling action.

Example 3 and Comparative Examples 5 to 6 Three types of hair styling mousse bases having the compositions shown in Table 5 were prepared, and the styling mousse base and liquefied petroleum gas (LPG) were mixed at 90:10 (weight ratio). ) Was used to fill a spray container into a styling mousse, and the hair was subjected to permanent wave treatment, and the hair was evaluated for ease of cohesion, luster, moisturization, combability, and tensile strength of hair.

In Example 3, as the silylated peptide,
In the general formula (I), R ¹ , R ² and R ³ are all O
H, a = 1, average value of m = 1, average value of n = 8, m
An average value of + n = 9, and a silylated hydrolyzed casein having a silyl functional group introduction rate of 64% is used. In Comparative Example 5,
Amodimethicone emulsion [Toray Dow Corning Silicone SM8702C (trade name)] as a silicone oil instead of silylated hydrolyzed casein
In Comparative Example 6, neither silylated peptide nor silicone was used.

[0071]

[Table 5]

Prior to the treatment with the hair styling mousse, a hair bundle having a length of 15 cm and a weight of 1 g was washed with a 2% aqueous polyoxyethylene nonylphenol solution, rinsed with water, and then the hair bundle was subjected to the following procedure. Wave processed. That is, each hair bundle has a diameter of 10 cm and a length of 8
A 6 cm thioglycolic acid solution (5 ml) adjusted to pH 9.2 with 28% ammonia water was applied on the rod, and the rod was covered with a wrap and left for 15 minutes. After washing for 10 seconds in running water, apply 5 ml of 6% sodium bromate solution, cover with plastic wrap and leave for 15 minutes, then wash in running water for 3 seconds.
Washed for 0 seconds.

The hair bundle was removed from the rod, and 2 g of the hair styling mousse agent of Example 3 and Comparative Examples 5 to 6 was applied to each hair bundle by rubbing, and then dried with a hair dryer. .

The dried hair was evaluated by 10 panelists (6 females and 4 males) for gloss, moisture and combability according to the same evaluation criteria as in Example 1.

Thirty hairs were taken out from each of the above hair bundles, and the tensile strength of each hair was measured. That is, after measuring the cross-sectional area by measuring the major axis and the minor axis of the portion 7.5 cm from the end of each hair with a micrometer, the tensile strength of the portion is measured by a tensile tester [Fudo Kogyo Co., Ltd., Rheometer]. And the tensile strength per cross-sectional area was calculated.

In the tensile strength test, the permanent wave-treated hair not treated with the hair styling mousse has a tensile strength of 28.4 kgf /
mm ² , and based on this, the strength increase rate of the hair treated with each hair styling mousse agent was calculated. The results are shown in Table 6. All evaluation values are average values.

[0077]

[Table 6]

As shown in Table 6, when the hair styling mousse agent of Example 3 was used, Comparative Example 5 and Comparative Example 6 were obtained.
Compared to using the hair styling mousse of
The evaluation values were high for all items of hair gloss, moisturization, and combability, and the tensile strength of the hair increased about 2.5 times that of Comparative Example 6 compared to Comparative Example 6, and the silylated hydrolyzate was used. It has been shown that degraded casein sorbs on the hair and contributes to the recovery of damaged hair. Comparative Example 5
The tensile strength was lower than that of Comparative Example 6, but it is considered that this is because the hair was damaged by the permanent wave treatment, the silicone was difficult to sorb on the damaged hair, and there was no action to recover the damaged hair.

Example 4 and Comparative Example 7 A hair liquid having the composition shown below was prepared. In this hair liquid, as the silylated peptide, R ¹ ═CH ₃ , R ² ═OH, R ³ ═O in the general formula (I) is used.
H, a = 3, average value of m = 1, average value of n = 7, m +
A silylated hydrolyzed wheat protein having an average value of n = 8 and a silyl functional group introduction rate of 65% is used.

Separately, a hair liquid having the same composition as in Example 4 except that the silylated hydrolyzed wheat protein was not added, and the amount of sterilized ion-exchanged water was increased, was prepared. Example 7 is set. In addition, the compounding quantity of each component is a weight part.

[0081]   Silylated hydrolyzed wheat protein (m + n = 8), (20%) 12.5   Acrylic acid alkyl ester / methacrylic acid alkyl ester 1.0   Copolymer (Plastic size L-53P, 50%, made by Kyosho Chemical Co., Ltd.)   Polyoxypropylene butyl ether (40EO) 20.0   Ethanol 50.0   Disodium edetate 0.1   Fragrance suitable amount   Sterilized ion-exchanged water Total 100

The following evaluations were carried out on the above hair liquids. That is, to five male panelists, once a day,
The hair liquid of Comparative Example 7 was used for the first 5 days, and the hair liquid of Example 4 was used for the next 5 days. After using the hair liquid of Example 4 for 5 days,
They asked whether the easiness of cohesion of hair, gloss, moisture and combability were better, worse, or unchanged than when the hair liquid of Comparative Example 7 was used. The results are shown in Table 7.

[0083]

[Table 7]

As shown in Table 7, after all the panelists used the hair liquid of Example 4 containing the silylated hydrolyzed wheat protein, the easiness of cohesion of hair, luster, moisturization and comb were compared with those before use. It was replied that the passability was improved, and it was revealed that the silylated hydrolyzed wheat protein has the effect of imparting luster and moisture to the hair, improving combability, and improving the hair setting property. Was there.

[Storage stability of water-soluble hairdressing preparation containing silylated peptide] The set lotion of Example 1 and the hair liquid of Example 4 were stored at room temperature (15 to 25 ° C) for 45 days to prevent precipitation and layer separation. It was visually observed whether or not it occurred, but no turbidity or layer separation occurred. The hair styling gel of Example 2 was in a gel form, and the hair styling mousse of Example 3 was filled in a liquefied petroleum gas and a spray container, and precipitation and layer separation could not be observed. .

─────────────────────────────────────────────────── ─── Continuation of the front page (72) Sukeko Oumi 1-2-14, Nunoichi-cho, Higashiosaka-shi, Osaka Prefecture Seiwa Kasei Co., Ltd. (56) Reference JP-A-3-223207 (JP, A) Kaihei 4-368317 (JP, A) JP-A 5-221836 (JP, A) JP-A 61-12609 (JP, A) (58) Fields investigated (Int.Cl. ⁷ , DB name) A61K 7 / 11

Claims (3)

(57) [Claims] 1. In a water-soluble hair styling composition containing a water-soluble polymer setting agent, the following general formula in which a functional group containing only one silicon atom is covalently bonded to the amino group of a peptide containing the amino group of the amino acid side chain: (I) [In the formula, at least two of R ¹ , R ² and R ³ represent a hydroxyl group, and the rest represent a methyl group. R ⁴ represents a residue excluding the terminal amino group of a basic amino acid having an amino group at the end of the side chain, R ⁵ represents a side chain of an amino acid other than R ⁴ ,
a is 1 or 3, m is greater than 0 and 50 or less , and n is 1
~ 200, m + n is 2 to 200 (however, m and n only indicate the number of amino acids and do not indicate the order of amino acid sequences)],
Alternatively, the following general formula (II): ^{Wherein, R 1, R 2, R} 3 2 or Chi caries represents a hydroxyl group,
The rest represent methyl groups. R ⁴ represents a residue excluding the terminal amino group of a basic amino acid having an amino group at the end of the side chain, R ⁵ represents a side chain of an amino acid other than R ⁴ , a is 1 or 3, and m is 0. Greater than 50 and n is 1 to 20
0, m + n is 2 to 200 (however, m and n only indicate the number of amino acids, and do not indicate the order of amino acid sequences)]. Water-soluble hair dressing. 2. The amount of the silylated peptide compounded is 0.1 to 2.
The water-soluble hair styling product according to claim 1, which is 0% by weight. 3. The content of the water-soluble polymer setting agent is 0.1.
The water-soluble hair styling agent according to claim 1 or 2, which is 10% by weight.