JPH11302300A - Cosmetic - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new acylated peptide usable in e.g. hair cosmetics having remarkable effect on hair damage prevention and recovery from hair damage, by condensation reaction between a protein-derived peptide formed by hydrolyzing the corresponding protein and a specific lanolin-derived nonhydroxyfatty acid. SOLUTION: This new acylated peptide (salt) is obtained by condensation reaction between a protein-derived peptide afforded by hydrolyzing the corresponding protein and a lanolin-derived nonhydroxyfatty acid containing 30-45 wt.% of a 10-31C iso-type fatty acid, 30-50 wt.% of a 11-31C anti-iso type fatty acid with the total content of the above two kinds of fatty acid being >=60 wt.%, and containing <10 wt.% of hydroxyfatty acid (s). This new acylated peptide is excellent in hair damage prevention and recovery from hair damage and useful in hair cosmetics capable of markedly improving hair feel of touch such as wiriness, dampishness and luster, and in skin cosmetics having skin- protective effect or skin-moisturizing effect and excellent feeling when applied.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to cosmetics and an acylated peptide suitable for being incorporated into the cosmetics.

2. Description of the Related Art In recent years, various types of chemical treatments such as permanent waving and hair dyeing, and beauty treatments, and further, the effects of ultraviolet rays and exhaust gas make the surface of the hair hydrophilic or damage the hair pelts on the surface. In addition, the damage to the hair such that even the fur cortex undergoes a structural change is increasing. Such damage to the hair causes split ends and cut hairs, and deteriorates the color, luster and texture of the hair. As one of the means to prevent such damage to the hair and to restore the damaged hair to its original properties, acylate the hydrolyzate of a protein known to have a moisturizing property with a higher fatty acid. A shampoo, a rinse, which contains an acylated peptide that imparts the ability to reduce the frictional force of the hair surface together with the surfactant activity.
Various hair cosmetics such as treatments have been proposed. For example, JP-A-63-105000 discloses various cosmetics containing an acylated peptide obtained by adding an acyl group having 8 to 20 carbon atoms to a casein-derived peptide. Japanese Patent No. 60086 discloses a fatty acid halide having 8 to 22 carbon atoms and an average molecular weight of 200 to 1
A shampoo containing an acylated peptide obtained by acylating 000 peptides is disclosed. In addition, for the purpose of protecting the skin and moisturizing, the formulation of such an acylated peptide into skin cosmetics has been proposed.

[0002]

However, even if such a known acylated peptide is incorporated into a cosmetic for hair, a sufficiently satisfactory effect can be always obtained in preventing hair damage and recovering damaged hair. Not been. In particular, the texture, feel, and feeling of use of the hair are still insufficient. In addition, satisfactory effects have not been obtained with respect to skin cosmetics in terms of feel, feeling of use, and the like.

[0003]

Means for Solving the Problems The present inventors have conducted intensive studies to solve the problems of such known hair cosmetics and skin cosmetics, and as a result, obtained by hydrolyzing proteins. By a method of blending an acylated peptide or a salt thereof obtained by condensing a protein-derived peptide with a lanolin fatty acid having a specific composition in a cosmetic for hair, it is possible to prevent hair damage and to obtain satisfactory results for recovery of damaged hair. It has been found that it is possible to significantly improve the moist feeling, the feel of hair, the luster, etc.

Further, it has been found that skin cosmetics containing this acylated peptide or a salt thereof have a sufficient skin protecting and moisturizing effect and show an excellent feeling of use. did.

That is, the present invention provides a protein-derived peptide obtained by hydrolyzing a protein,
30 to 45% by weight of 31 iso-type fatty acids, 11 to 11 carbon atoms
30 to 50% by weight of 31 anteiso fatty acids and 10 to 30% by weight of normal fatty acids having 10 to 30 carbon atoms
Wherein the total amount of the iso-type fatty acid and the anteiso-type fatty acid is at least 60% by weight and the content of the hydroxy fatty acid is less than 10% by weight, and the acylation obtained by condensing the non-hydroxy fatty acid derived from lanolin. A peptide or a salt thereof is provided.

Here, the iso-type fatty acids, anteiso-type fatty acids and normal-type fatty acids are compounds represented by the following structural formulas. * Iso-type fatty acid CH3-CH (CH3)-(CH2) n-COOH (n = 6 ~
27) * Anteiso fatty acid CH3CH2-CH (CH3)-(CH2) n-COOH (n
= 6-26) * Normal fatty acid CH3- (CH2) n-COOH (n = 8-28) The hydroxy fatty acid is a fatty acid having a hydroxyl group in the molecule, and is, for example, the following α-position or Fatty acids having a hydroxyl group at the ω-position are included. CH3- (CH2) n-CH (OH) -COOH (n = 7-
29) CH3-CH (CH3)-(CH2) n-CH (OH) -CO
OH (n = 7-29) CH3-CH2-CH (CH3)-(CH2) n-CH (OH)
-COOH (n = 5 to 27) CH2 (OH)-(CH2) n-COOH (n = 20 to 3)
4)

[0007] The present invention further provides a protein-derived peptide obtained by hydrolyzing a protein, a peptide having 10 to 3 carbon atoms.
30 to 45% by weight of 1 iso-type fatty acid, 11 to 13 carbon atoms
1 to 30% by weight of an anteiso-type fatty acid and 10 to 30% by weight of a normal-type fatty acid having 10 to 30 carbon atoms, wherein the total amount of the iso-type fatty acid and the anteiso-type fatty acid is at least 60% by weight, and Cosmetics containing an acylated peptide or a salt thereof obtained by condensing lanolin-derived non-hydroxy fatty acids having a hydroxy fatty acid content of less than 10% by weight (hereinafter referred to as non-hydroxy lanolin fatty acids), such as hair Cosmetics, skin cosmetics and the like.

[0008] The non-hydroxylanolin fatty acid used in the present invention, an iso-type fatty acid having 10 to 31 carbon atoms, 1 carbon atom
1 to 31 anteiso fatty acids and 10 to 30 carbon atoms
Has a carbon number of preferably 15 to 24, and more preferably 17 to 22. Further, the content of the branched fatty acid having 20 or more carbon atoms (iso-type fatty acid, anteiso-type fatty acid) is preferably less than 40% by weight. Furthermore, the number of carbon atoms in non-hydroxylanolin fatty acid is 10
The content of the iso-type fatty acid of from 30 to 31 is preferably from 30 to 35.
% By weight, the content of the anteiso fatty acid having 11 to 31 carbon atoms is preferably 35 to 45% by weight and 10 to 3 carbon atoms.
The normal fatty acid content of 0 is preferably 12 to 16
% By weight.

The non-hydroxylanolin fatty acid used in the present invention can be produced by the method described in JP-A-6-293614. That is, a known lanolin fatty acid or a lower alcohol ester thereof is borated and distilled to obtain a non-hydroxylanoline fatty acid or a lower alcohol ester thereof and a boric acid ester of a hydroxylanolin fatty acid or a lower alcohol ester thereof. Can be However, the production method is not particularly limited, and any method capable of obtaining a fatty acid having the above composition can be employed.

[0010] The protein-derived peptide used in the present invention can be obtained by a method of hydrolyzing a protein using an acid, an alkali, or a protease.
The molecular weight of this protein-derived peptide is 100-300
00, preferably 200-5000. (Note that
In the present specification, the molecular weight of the protein-derived peptide is a number average molecular weight. ) The molecular weight of the protein-derived peptide can be adjusted by appropriately selecting the amount of acid, alkali, and enzyme used in the hydrolysis, the reaction temperature, and the reaction time. Production of the protein-derived peptide used in the present invention is described in JP-A-63-105000,
It can be carried out under the same method and conditions as those described in Japanese Patent Publication No. 4-60086. Natural proteins are preferably used as proteins used for the production of peptides. Among natural proteins, collagen,
Keratin, silk protein, casein, soy protein, and wheat protein can be particularly preferably used. Here, the soybean protein is a protein obtained from soybean or the like, and is obtained by, for example, isoelectrically precipitating an aqueous extract of defatted soybean seeds at pH 4-5. Wheat protein is a protein obtained from wheat or the like, and is obtained, for example, by isoelectrically precipitating an aqueous extract of wheat seeds. Silk protein
It is a protein obtained from silkworm cocoons, silk thread, silk cloth, etc. Further, as the protein-derived peptide used in the present invention, various commercially available protein-derived peptides can be used. For example, a collagen-derived peptide (Clothein A, manufactured by Croda Japan KK), a keratin-derived peptide (produced by Seiwa Chemical Co., Ltd., Promois WK-H)
P), silk protein-derived peptide (produced by Seiwa Kasei, Promois Silk-700SP), casein-derived peptide (produced by Seiwa Kasei, Promois Milk-P),
Soy protein-derived peptide (Croda Japan K.K.)
Manufactured by Hydrosoi 2000SF) and a wheat protein-derived peptide (Hydrotriticum 2000 manufactured by Croda Japan KK) can be used.

[0011] The condensation of non-hydroxylanolin fatty acids with protein-derived peptides can be carried out as follows. That is, most commonly, protein-derived peptides are converted to Schotten-Bau.
mann) reaction, pH 7-14, preferably pH 8
Acylation is performed using an acid halide of a non-hydroxylanolin fatty acid in an aqueous solution under alkaline conditions of 10 to 10 to obtain an acylated peptide. At that time, the pH decreases with the progress of the reaction. Therefore, the pH is maintained by adding an alkali such as sodium hydroxide or potassium hydroxide. Reaction temperature is 0-60
The reaction is carried out at a temperature of 20 ° C., preferably 20 to 40 ° C. for 1 to 6 hours.
Acid chlorides are most commonly used as acid halides, but acid halides such as acid bromide and acid iodide can also be used.

The above-mentioned Schotten-Baumann (Schott)
Ten-Baumann) reaction, 150 to 20
A method in which non-hydroxylanolin fatty acid or a lower alcohol ester thereof and a protein-derived peptide are subjected to dehydration condensation or dealcoholation condensation at a high temperature of 0 ° C. and a high pressure can also be adopted. In addition, a method in which a protein-derived peptide is subjected to a reduction treatment to generate a thiol group, and then, in the presence or absence of an acid or an alkali catalyst, a method of heating with a non-hydroxylanolin fatty acid to generate an ester may be employed.

[0013] The acylated peptide thus obtained can be directly blended into a cosmetic after neutralization.
Preferably, the precipitate is recovered by pouring it into an aqueous solution of a strong acid such as hydrochloric acid or sulfuric acid, and the precipitate is washed with water and purified. The acylated peptide thus obtained is used in a free form or in a salt form after neutralization. The acylated peptide thus obtained is prepared as a solution of water or alcohol, a polyhydric alcohol such as propylene glycol, or
It is dried and used as a powder. The concentration of the solution is preferably 10 to 60% by weight, more preferably 2 to 60% by weight.
0 to 40%. As the alkali used for neutralization,
Caustic alkalis such as sodium hydroxide and potassium hydroxide,
Ammonia or monoethanolamine, diethanolamine, triethanolamine, 2-amino-2
Organic alkanolamines such as -methyl-1,3-propanediol can be preferably used.

The cosmetics of the present invention include hair cosmetics, skin cosmetics, foundations, lipsticks, soaps,
Nail cosmetics and the like. The acylated peptide of the present invention or a salt thereof is particularly preferably used for cosmetics for hair and cosmetics for skin.

The hair cosmetics of the present invention refer to all the cosmetics applied to the hair, such as shampoos, rinses, conditioners, hair packs and other hair wash cosmetics, hair creams, hair tonics, and the like. Hair cosmetics such as hair spray, permanent wave solution, hair dye, color rinse, bleaching agent, hair chemicals that may damage the hair by any chemical treatment such as color nail polish, hair dryer, etc. Hair styling materials such as mousse and gel used for hot air treatment are included. The skin cosmetics of the present invention include face wash, lotion, cream, emulsion and the like. Further, the cosmetic of the present invention may be an aqueous solution, an ethanol solution, an emulsion,
Various dosage forms such as suspension, gel, liquid crystal, solid, and aerosol can be used.

The amount of the acylated peptide of the present invention or a salt thereof in a hair cosmetic is about 0.01 to 20% by weight for a non-aqueous oil type, and 0.1% for a non-aqueous cream type. About 01 to 30% by weight, about 0.1 to 30% by weight for shampoo, about 0.1 to 20% by weight for rinsing, and 0.01 to 30% for the first agent for permanent wave. About 20% by weight, preferably about 0.1 to 10% by weight, and in the case of a hair dye, 0.01 to 2% by weight.
About 0% by weight, preferably about 0.1 to 10% by weight, about 0.05 to 10% by weight for color nail polish, about 0.05 to 10% by weight for bleaching agent, hair styling such as mousse and gel In the case of an agent, the content is preferably about 0.05 to 10% by weight. The amount of the cream, milky lotion or the like to be added to the cosmetic for skin is preferably about 0.05 to 10% by weight.

In the cosmetic of the present invention, any component of a known cosmetic composition can be used as a component other than the acylated peptide of the present invention or a salt thereof. For example,
The hair cosmetic composition of the present invention may contain optional components described in JP-B-6-39592, JP-A-8-310920 and the like.

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

Example 1 Non-hydroxylanolin fatty acid /
Synthesis of Collagen-Derived Peptide Condensate Potassium Salt Non-hydroxylanolin fatty acid (acid value 180, carbon number 10
34.4% by weight of isoform fatty acid having a carbon number of 11 to 31
Average of fatty acid content of isotype fatty acid, anteiso type fatty acid and normal type fatty acid of 39.2% by weight of normal type fatty acid content of 10 to 30 carbon atoms and 2.4% by weight of hydroxy fatty acid Content of iso-fatty acid and anteiso-fatty acid having 19.3 carbon atoms and 20 to 32 carbon atoms: 38.6% by weight) 312
g (1 mol) was melted at 55 ° C. Thereto, 69 g (0.5 mol) of phosphorus trichloride was added dropwise over about 30 minutes, and then 5
The mixture was stirred at 5 to 60 ° C for 3 hours and left for 8 hours. Thereafter, the lower layer of phosphorous acid was removed to obtain a crude acid chloride.
The crude acid chloride was distilled with a glass distillation apparatus to obtain 324 g of the acid chloride. Collagen-derived peptide (manufactured by Nikko Chemicals Co., Ltd., CCP-100P, average molecular weight 10)
00) 44.6 g of the acid chloride thus obtained (0.9 equivalents of collagen-derived peptide) was added to a solution obtained by dissolving 150 g in 350 g of water at 40 ° C. for 2 hours while stirring. It dripped over. After completion of dropping, at 40 ° C 1
After stirring for an hour, the temperature was further raised to 45 ° C., and the mixture was stirred for 1 hour to complete the reaction. During the reaction, a 20% aqueous sodium hydroxide solution was appropriately added dropwise to maintain the pH of the reaction solution at 9.0.
After the completion of the reaction, the reaction solution was poured into 5 liters of a 5% aqueous sulfuric acid solution, and the lower aqueous layer was removed, whereby the generated acylated product was separated as a floating precipitate. Further, by adding this acylated product to water and then removing the lower aqueous layer,
Washed with water. The obtained acylated product was neutralized and dissolved with a 30% aqueous potassium hydroxide solution, and the concentration was adjusted to obtain 587 g of a 30% aqueous solution of a potassium salt of a condensate of a non-hydroxylanolin fatty acid and a collagen-derived peptide. This is abbreviated as NH-collagen-K salt.

Example 2 Non-hydroxylanolin fatty acid /
Synthesis of sodium salt of silk protein-derived peptide condensate 150 g of collagen-derived peptide of Example 1 was added to 350 parts of water.
g, and then changed to a solution obtained by dissolving the protein in silk protein-derived peptide (promois silk-manufactured by Seiwa Kasei Co., Ltd.).
700SP, average molecular weight 350) 52.5 g in water 175
g of sodium hydroxide of the condensate of non-hydroxylanolin fatty acid and silk protein-derived peptide, except that a solution obtained by dissolving the non-hydroxylanoline fatty acid and the silk protein-derived peptide was used. 301 g of a 30% aqueous solution was obtained. This is abbreviated as NH-silk-Na salt.

Example 3 Non-hydroxylanolin fatty acid /
Synthesis of sodium salt of keratin-derived peptide condensate 150 g of collagen-derived peptide of Example 1 was added to 350 parts of water.
g), and a solution obtained by dissolving 150 g of keratin-derived peptide (promois WK-HP, average molecular weight 1000) (produced by Seiwa Chemical Co., Ltd.) in 350 g of water is used, and The same operation as in Example 1 was carried out except that potassium hydroxide was changed to sodium hydroxide, to obtain 613 g of a 30% aqueous solution of a sodium salt of a condensate of a nonhydroxylanolin fatty acid and a keratin-derived peptide. This is N
Abbreviated as H-keratin-Na.

Example 4 Non-hydroxylanolin fatty acid /
Synthesis of Wheat Protein Derived Peptide Condensate Triethanolamine Salt
g, and 750 g of wheat protein-derived peptide (manufactured by Croda Japan Co., Ltd., Hydrotriticum 2000, average molecular weight 3000, 20% aqueous solution) was used. The procedure was the same as that of Example 1 except that triethanolamine was used instead of potassium hydroxide, and 30% of triethanolamine salt of a condensate of non-hydroxylanolin fatty acid and wheat protein-derived peptide was used. 503 g of an aqueous solution was obtained. This is abbreviated as NH-wheat-T salt.

Example 5 Non-hydroxylanolin fatty acid /
Synthesis of Silk Protein-Derived Peptide Condensate 2-Amino-2-methyl-1,3-propanediol Salt Sodium hydroxide as a neutralizing agent of Example 2 was replaced with 2-amino-2-
The same operation as in Example 2 was carried out except that methyl-1,3-propanediol was used, and the 2-amino-2-condensate of a non-hydroxylanolin fatty acid and a silk protein-derived peptide condensate was used.
25% aqueous solution of methyl-1,3-propanediol salt 36
0 g was obtained. This is NH-silk-2-amino-2-methyl-
Abbreviated as 1,3-propanediol salt.

Example 6 Non-hydroxylanolin fatty acid /
Casein-derived peptide condensate 2-amino-2-methyl-1,
Synthesis of 3-propanediol salt 150 g of the collagen-derived peptide of Example 1 was
g of a solution obtained by dissolving 90 g of casein-derived peptide (promois milk-P, manufactured by Seiwa Kasei Co., Ltd., average molecular weight 600) in 210 g of water, and Example 1 except that potassium hydroxide was changed to 2-amino-2-methyl-1,3-propanediol
The same operation as described above was carried out to obtain the 2-amino-2-methyl-1,3
510 g of a 25% aqueous solution of -propanediol salt were obtained.
This is abbreviated as NH-casein-2-amino-2-methyl-1,3-propanediol salt.

Example 7 Non-hydroxylanolin fatty acid /
Synthesis of potassium salt of soy protein-derived peptide condensate 150 g of collagen-derived peptide of Example 1 was added to 350 parts of water.
g, and then converted to a solution obtained, soybean protein-derived peptide (manufactured by Croda Japan K.K., Hydrosoy 2000SF, average molecular weight 4000, 20% aqueous solution) 7
Using the same procedure as in Example 1 except that 50 g was used and the amount of the acid chloride dropped was changed to 11.2 g, 710 g of a 20% aqueous solution of a potassium salt of a condensate of a non-hydroxylanolin fatty acid and a soybean protein-derived peptide was used. I got This is NH
-Abbreviated as Soy-K Salt.

Comparative Example 1 Synthesis of potassium salt of myristate / collagen-derived peptide condensate Myristate (NAA142, manufactured by NOF Corporation) 22
8 g (1 mol) were melted at 55 ° C. After dropping 69 g (0.5 mol) of phosphorus trichloride over about 30 minutes,
Stir at 55-60 ° C for 3 hours and leave for another 8 hours. Thereafter, the lower layer of phosphorous acid was removed to obtain a crude acid chloride. The crude acid chloride is distilled with a glass distillation apparatus,
230 g of acid chloride were obtained. In a solution obtained by dissolving 150 g of collagen-derived peptide (manufactured by Nikko Chemicals Co., Ltd., CCP-100P, average molecular weight: 1000) in 350 g of water, 33.3 g of the acid chloride thus obtained (collagen-derived peptide) 0.9 equivalents) was added dropwise at 40 ° C. over 2 hours with stirring. After completion of the dropwise addition, the mixture was stirred at 40 ° C. for 1 hour, and the temperature was further raised to 45 ° C., and the mixture was stirred for 1 hour to complete the reaction. During the reaction, a 20% aqueous sodium hydroxide solution was appropriately added dropwise to maintain the pH of the reaction solution at 9.0. After the completion of the reaction, the reaction solution was poured into 5 liters of a 5% aqueous sulfuric acid solution, and the lower aqueous layer was removed, whereby the generated acylated product was separated as a floating precipitate. Further, the acylated product was added to water, and then the lower aqueous layer was removed to wash with water. The obtained acylated product was neutralized and dissolved with a 30% aqueous solution of potassium hydroxide, and the concentration was adjusted to obtain 590 g of a 30% aqueous solution of a potassium salt of a condensate of myristic acid and a collagen-derived peptide. This is myristine
-Collagen-K salt.

Comparative Example 2 Synthesis of sodium salt of lanolin fatty acid / keratin-derived peptide condensate Lanolin fatty acid (manufactured by Nippon Seika Co., Ltd., lanolin fatty acid A, isotype fatty acid having 10 to 31 carbon atoms: 24.6% by weight, carbon 31. Content of anteiso type fatty acids of formulas 11 to 31
0% by weight, 13.3% by weight of normal fatty acid having 10 to 30 carbon atoms, 18.5% by weight of hydroxy fatty acid, average number of carbon atoms of iso-type fatty acid, anteiso-type fatty acid and normal-type fatty acid 21.1) 330 g (1 mol)
Was melted at 55 ° C. There, 69 g of phosphorus trichloride (0.
5 mol) was added dropwise over about 30 minutes, and the mixture was stirred at 55 to 60 ° C. for 3 hours and left for 8 hours. Thereafter, the lower layer of phosphorous acid was removed to obtain a crude acid chloride. The crude acid chloride was distilled with a glass distillation apparatus to obtain 270 g of the acid chloride. To a solution obtained by dissolving 150 g of keratin-derived peptide (promois WK-HP, manufactured by Seiwa Chemical Co., Ltd., average molecular weight: 1000) in 350 g of water, 47 g of the acid chloride thus obtained (keratin-derived peptide) 0.9
Was added dropwise at 40 ° C. over 2 hours with stirring.
After the addition, the mixture was stirred at 40 ° C. for 1 hour,
C. and the reaction was completed by stirring for 1 hour. During the reaction, a 20% aqueous sodium hydroxide solution was appropriately added dropwise to maintain the pH of the reaction solution at 9.0. After the reaction is completed, 5%
By pouring into 5 liters of a sulfuric acid aqueous solution and removing the lower aqueous layer, the generated acylated product was separated as a floating precipitate. Further, the acylated product was added to water, and then the lower aqueous layer was removed to wash with water. After neutralizing and dissolving the obtained acylated product with a 30% aqueous sodium hydroxide solution, the concentration is adjusted, and a 30% aqueous solution of a sodium salt of a condensate of a lanolin fatty acid and a keratin-derived peptide is prepared.
g was obtained. This is abbreviated as lanolin-keratin-Na salt.

Comparative Example 3 Synthesis of Triethanolamine Salt of Isostearic Acid / Wheat Protein Derived Peptide Condensate After heating 291 g (1 mol) of isostearic acid (manufactured by Higher Alcohol Industry Co., Ltd., isostearic acid PK) to 55 ° C., 69 g (0.5 mol) of phosphorus chloride was added dropwise over about 30 minutes. Thereafter, the mixture was stirred at 55 to 60 ° C. for 3 hours, and further stirred at
Left for hours. Thereafter, the lower layer of phosphorous acid was removed to obtain a crude acid chloride. The crude acid chloride was distilled with a glass distillation apparatus to obtain 280 g of the acid chloride. 13.9 g of the acid chloride thus obtained (0.9 equivalents of the wheat protein-derived peptide) was added to a wheat protein-derived peptide (manufactured by Croda Japan Co., Ltd., Hydrotriticum 2).
000, average molecular weight 3000, 20% aqueous solution) 750 g
At 40 ° C. with stirring over 2 hours. After the completion of the dropwise addition, the mixture was stirred at 40 ° C. for 1 hour, further raised to 45 ° C., and stirred for 1 hour to complete the reaction. During the reaction, 2
A 0% aqueous sodium hydroxide solution is appropriately added dropwise, and p
H was kept at 9.0. After the completion of the reaction, the reaction solution was poured into 5 liters of a 5% aqueous sulfuric acid solution, and the lower aqueous layer was removed, whereby the generated acylated product was separated as a floating precipitate. Further, the acylated product was added to water, and then the lower aqueous layer was removed to wash with water. After neutralizing the obtained acylated product with triethanolamine and dissolving in water,
After adjusting the concentration, 30% of the triethanolamine salt of the condensate of isostearic acid and wheat protein-derived peptide was prepared.
530 g of a 30% aqueous solution was obtained. This is abbreviated as isostere-wheat-T salt.

Comparative Example 4 Isostearic acid / silk protein-derived peptide condensate 2-amino-2-methyl-1,3
-Synthesis of propanediol salt Silk protein-derived peptide (Promois Silk-700SP, average molecular weight 350) manufactured by Seiwa Chemical Co., Ltd.5
Dissolve 2.5 g in 175 g of water and stir at 40 ° C.
41.8 g of the acid chloride prepared in Comparative Example 3 (0.9 equivalents of the silk-derived peptide) was added dropwise over 2 hours. After the completion of the dropwise addition, the mixture was stirred at 40 ° C. for 1 hour, further raised to 45 ° C., and stirred for 1 hour to complete the reaction. During the reaction,
A 20% aqueous sodium hydroxide solution was appropriately added dropwise to maintain the pH of the reaction solution at 9.0. After the completion of the reaction, the reaction solution was poured into 5 liters of a 5% aqueous sulfuric acid solution, and the lower aqueous layer was removed, whereby the generated acylated product was separated as a floating precipitate. Further, the acylated product was added to water, and then the lower aqueous layer was removed to wash with water. The obtained acylated product is neutralized with 2-amino-2-methyl-1,3-propanediol and dissolved in water, and then the concentration is adjusted. The 2-amino-2-condensation product of isostearic acid and a silk protein-derived peptide is obtained. 368 g of a 25% aqueous solution of -2-methyl-1,3-propanediol salt was obtained. This is abbreviated as isostyl-silk-2-amino-2-methyl-1,3-propanediol salt.

Examples 8 to 9 and Comparative Examples 5 to 6 Four types of shampoo compositions having the compositions shown in Table 1 were prepared.
A performance evaluation test was conducted for the gloss and moist feeling after use and drying.

Evaluation method: A shampoo composition having the composition shown in Table 1 was used by 10 female panelists, and a sensory evaluation was conducted on gloss and moist feeling after use and drying. The results are shown in Table 1 based on the following evaluation criteria. ：: 7 to 10 people who answered good △: 4 to 6 people who answered good ×: 0 to 3 people who answered good

[0031]

[Table 1] The numerical values in the table are numerical values in which the amount is expressed in parts by weight.
In the table, "balance" means an amount necessary to make the total amount 100 parts by weight. The same applies to the following tables.

Examples 10 to 11 and Comparative Examples 7 to 8 Four types of rinse compositions having the compositions shown in Table 2 were prepared and subjected to performance evaluation tests for gloss and moist feeling after use and drying.

Evaluation method: A rinse composition having the composition shown in Table 2 was used by 10 female panelists, and sensory evaluation was performed on gloss and moist feeling after use and drying based on the same criteria as in Examples 8 and 9. . Table 2 shows the results.

[0034]

[Table 2]

Examples 12 to 13 and Comparative Examples 9 to 10 Four types of cold permanent wave liquid compositions having the compositions shown in Table 3 were prepared and subjected to performance evaluation tests for hair strength and moist feeling.

Evaluation method: (Moist feeling) Using a cold permanent wave liquid composition having the composition shown in Table 3, 10 female panelists were subjected to a permanent wave treatment, and the moist feeling after drying was evaluated in Examples 8 to 10. Sensory evaluation was performed based on the same criteria as in Example 9. Table 3 shows the results.

(Hair strength) Using black healthy hair of a 20-year-old female, the hair was washed with a 5% shampoo solution and thoroughly rinsed with running water. Thereafter, a hair bundle having a length of 15 cm and a weight of 5 g was prepared. The hair bundle was wound around a curler having a diameter of 1.3 cm, and immersed in the first permanent wave agent at 30 ° C. for 10 minutes. Furthermore, after washing with running water for 1 minute, it was immersed in the second permanent wave agent at 30 ° C. for 10 minutes. Thereafter, the plate was washed with running water for 1 minute, the curler was removed, and air-dried. Then, the hair bundle is suspended in a thermo-hygrostat at 25 ° C. and 70% humidity,
The specimen was left overnight.

Ten hairs having the same thickness (80 μm) were selected from the hair bundle, and one by one was subjected to a breaking load (tensile strength) using a tribo gear (surface property measuring device (TYPE: 14DR) manufactured by Shinto Kagaku Co., Ltd.). Was measured and the average value was taken as the hair strength. Table 3 shows the results. Similarly, when the hair was not subjected to the permanent wave treatment, the hair strength was measured to be 145 g. The higher the hair strength after the permanent wave treatment, the greater the effect of preventing hair damage.

[0039]

[Table 3]

Examples 14 to 15 and Comparative Examples 11 to 12 Four types of hair blow compositions having the compositions shown in Table 4 were prepared and subjected to a performance evaluation test for gloss and moist feeling after use and drying.

Evaluation method: A hair blow composition having a composition shown in Table 4 was used by 10 female panelists, and the gloss and moist feeling after use and drying were subjected to a sensory evaluation based on the same criteria as in Examples 8 and 9. Was. Table 4 shows the results.

[0042]

[Table 4]

Examples 16 to 17 and Comparative Examples 13 to 14 Four kinds of skin soap compositions having the compositions shown in Table 5 were prepared and subjected to a performance evaluation test for the moist feeling after use.

Evaluation method: A skin soap composition having the composition shown in Table 5 was used by 10 female panelists, and the moist feeling after use was evaluated organoleptically based on the same criteria as in Examples 8 and 9. Table 5 shows the results.

[0045]

[Table 5]

Example 18 and Comparative Examples 15 to 16 Three types of shampoo compositions having the compositions shown in Table 6 were prepared.
Each of the compositions was applied to the hair, and a performance evaluation test was performed on the easiness of uniting, gloss, moisture, and combability of the washed hair. In Example 18, the potassium salt of the condensate of the non-hydroxylanolin fatty acid synthesized in Example 7 and the soybean protein-derived peptide was added as the acylated peptide or a salt thereof to the composition. In Comparative Example 15, the potassium salt of the condensate of myristic acid and the collagen-derived peptide synthesized in Comparative Example 1 was added to the composition instead of the potassium salt of the condensate of the non-hydroxylanolin fatty acid and the soybean protein-derived peptide. In Comparative Example 16, the acylated peptide or a salt thereof was not added to the composition.

[0047]

[Table 6] Evaluation method: 20-year-old female black healthy hair, length 15c
A hair bundle having a weight of 1 g and a weight of 1 g was prepared. Table 6 shows the respective hair bundles.
Was washed with 1 g of each shampoo solution, rinsed with hot water and dried with a hair dryer. After repeating this shampoo process 5 times, the hair is easy to unite,
The gloss, moisture and combability were evaluated by 10 female panelists on a 5-point scale based on the following evaluation criteria. The results are shown in Table 7 as an average value of 10 persons.

Evaluation criteria 5: Very good 4: Good 3: Normal 2: Bad 1: Very bad

[0049]

[Table 7]

As shown in Table 7, the hair treated with the shampoo solution of Example 18 exhibited Comparative Example 15 regardless of the evaluation items of gloss, moisture, combability and unity.
And superior to the hair treated with the shampoo solution of Comparative Example 16. This result indicates that the potassium salt of an acylated peptide obtained by condensing a non-hydroxylanolin fatty acid with a soybean protein-derived peptide has an effect of imparting gloss and moisture to hair, an effect of improving combability of hair, and an effect of improving hair combability. This indicates that the composition is excellent in the action of facilitating cohesion.

Example 19 and Comparative Examples 17 to 18 Three kinds of hair treatment agents (hair treatment creams) having the compositions shown in Table 8 were prepared, and each of them was applied to the hair. A performance evaluation test was conducted for moisture, combability, and the like. In Example 19, as the acylated peptide or a salt thereof, a sodium salt of a condensate of the non-hydroxylanolin fatty acid synthesized in Example 3 and the keratin-derived peptide was added to the composition. Comparative Example 1
In 7, the sodium salt of the condensate of the lanolin fatty acid and the keratin-derived peptide synthesized in Comparative Example 2 was added to the composition instead of the sodium salt of the condensate of the non-hydroxylanolin fatty acid and the keratin-derived peptide. In Comparative Example 18, the acylated peptide or a salt thereof was not added to the composition.

[0052]

[Table 8] Evaluation method: 20-year-old female black healthy hair, length 15c
A hair bundle having a weight of 1 g and a weight of 1 g was prepared. After each hair bundle was washed with a commercially available shampoo, 2 g of each hair treatment agent shown in Table 8 was applied, and the hair was rinsed with hot water. After repeating the shampoo washing and the treatment with the hair treatment agent five times, the hair is easy to be united, glossy, moist and combable.
A female panel was evaluated on a 5-point scale based on the same evaluation criteria as in Example 18. The results are shown in Table 9 as an average value of 10 persons.

[0053]

[Table 9]

As shown in Table 9, the hair treated with the hair treating agent of Example 19 showed that the hair of Comparative Examples 17 and 18 had any of the evaluation items of gloss, moisture, combability and unity. Better than hair treated with treatment agents. This result indicates that the sodium salt of the acylated peptide obtained by condensing the non-hydroxylanolin fatty acid with the keratin-derived peptide has the effect of imparting gloss and moisture to the hair, the effect of improving the combability of the hair, and the cohesion of the hair. It shows that it is excellent in the effect of making it easier. The sodium salt of the acylated peptide obtained by condensing the lanolin fatty acid and the keratin-derived peptide of Comparative Example 2 also has the effect of imparting gloss and moisture to the hair, the effect of improving the combability of the hair, and the ease of cohesion of the hair. Table 9 shows that the sodium salt of an acylated peptide obtained by condensing a non-hydroxylanolin fatty acid with a keratin-derived peptide is even better.
The results are shown. Example 20 and Comparative Examples 19 to 20 Three kinds of first agents for permanent wave having the compositions shown in Table 10 were prepared, and each of the first agents and the second agent for permanent wave comprising a 6% aqueous sodium bromate solution. The hair bundle was subjected to a permanent wave treatment using, and the gloss and moisture of the treated hair were subjected to a sensory evaluation, and the hair strength (tensile strength) and the amount of cysteic acid in the hair were examined. In Example 20, a potassium salt of a condensate of a non-hydroxylanolin fatty acid synthesized in Example 1 and a collagen-derived peptide was added to the composition as an acylated peptide or a salt thereof. In Comparative Example 19, the potassium salt of the condensate of myristic acid and the collagen-derived peptide synthesized in Comparative Example 1 was added to the composition instead of the potassium salt of the condensate of the non-hydroxylanolin fatty acid and the collagen-derived peptide. In Comparative Example 20, the acylated peptide or a salt thereof was not added to the composition.

[0055]

[Table 10] Evaluation method: (Sensory evaluation) Using healthy black hair of women in their 20s, length 2
A hair bundle of 0 cm and a weight of 1 g was prepared. Each hair bundle,
Washed with commercial shampoo. The washed hair bundles were wound around rods each having a diameter of 1 cm and a length of 8 cm, and both ends were fixed with rubber bands. Then, 2 ml of each of the first agents for permanent wave shown in Table 10 was added to each hair bundle.
The rods were covered with wrap and left for 15 minutes. Thereafter, each hair bundle was washed in running water for 10 seconds, and then 2 ml of a permanent waving second agent composed of a 6% aqueous sodium bromate solution was applied to each hair bundle, covered with a wrap, and left for 15 minutes. Then, after gently washing in running water for 30 seconds, the hair bundle was dried in a dryer at 50 ° C. for 20 minutes to remove the hair bundle from the rod. Thereafter, the gloss and moisture of the hair were evaluated by ten female panelists based on the same evaluation criteria as in Example 18 in five steps. The results are shown in Table 11 as an average value of 10 persons. (Hair Strength) The tensile strength of hair was measured as follows. That is, each of the hair bundles after the sensory evaluation is 40
Take out the hair of each book and place it at the center of each hair (10c from the hair end)
m) Measure the major axis and minor axis with a micrometer and calculate the cross-sectional area, excluding 5 hairs each from the larger and smaller cross-sectional areas from the test object, and the tensile strength of the remaining 30 hairs Was measured. In the measurement of the tensile strength, an adhesive tape [Scotch filament tape, manufactured by Sumitomo 3M Ltd.] was fixed to the hair at intervals of 0.5 mm before and after the portion where the cross-sectional area was measured. After that, the part where this tape was fixed was pulled by a tensile tester [Fudo Kogyo Co., Ltd.
And the strength of the cut hair was measured. From the strength at the time of cutting and the cross-sectional area determined earlier, the tensile strength per cross-sectional area (kgf / mm
2) was calculated. Table 11 shows the results. (Amount of cysteic acid) Further, 2 g of 6N hydrochloric acid was added to 0.01 g of hair taken out from each hair bundle, and the hair was left at 105 ° C. for 20 hours so that the protein of the hair was completely hydrolyzed. Thereafter, the amount of cysteic acid (μmol / g) was determined by an automatic amino acid analyzer. Table 11 shows the results. The amount of cysteic acid in the hair indicates the degree of damage to the hair, and the smaller the value, the less damage to the hair.

[0056]

[Table 11]

As shown in Table 11, the hair subjected to the permanent wave treatment using the first permanent wave agent containing the potassium salt of the condensate of the non-hydroxylanolin fatty acid and the collagen-derived peptide of Example 20 Is superior to the hair treated with the first agent for permanent wave of Comparative Examples 19 and 20 in any of the evaluation items of gloss and moisture, furthermore, the tensile strength of the hair is large, and the cysteic acid in the hair is high. The amount is small. In addition, this result indicates that the potassium salt of an acylated peptide obtained by condensing a non-hydroxylanolin fatty acid and a collagen-derived peptide is excellent in the effect of imparting gloss and moisture to the hair, and that the hair is treated with a permanent wave. It is also excellent in preventing damage and increasing the tensile strength of hair.

Example 21 and Comparative Examples 21 to 22 A first agent of three kinds of oxidative hair dyes having compositions shown in Table 12 and a second agent of oxidative hair dyes having compositions shown in Table 13 were prepared. The hair was subjected to a hair dyeing treatment, and the gloss, moisture and combability of the treated hair were subjected to a sensory evaluation, and the strength of the hair (tensile strength) and the amount of cysteic acid in the hair were examined. In Example 21, the 2-hydroxylanolin fatty acid synthesized in Example 5 and the condensate of the silk protein-derived peptide were used as the acylated peptide or a salt thereof.
Amino-2-methyl-1,3-propanediol salt was added to the composition. In Comparative Example 21, 2-condensate of non-hydroxylanolin fatty acid and silk protein-derived peptide was used.
Instead of amino-2-methyl-1,3-propanediol salt, 2-amino-2-methyl-condensate of isostearic acid synthesized in Comparative Example 4 with a silk protein-derived peptide
A 1,3-propanediol salt was added to the composition. In Comparative Example 22, the acylated peptide or a salt thereof was not added to the composition.

[0059]

[Table 12]

[0060]

[Table 13] Evaluation method (Sensory evaluation) Using healthy black hair of women in their 20s, length 1
A hair bundle of 5 cm and a weight of 1 g was prepared. Table 1 shows each hair bundle.
The hair was dyed using 2 g of a mixture obtained by mixing the first agent of No. 2 and the second agent of Table 13 in equal amounts. After the hair was dyed, the hair was rinsed with lukewarm water, dyed again with the same amount of the hair dye, washed with a 2% aqueous solution of polyoxyethylene nonylphenyl ether, and dried with a hair dryer. After drying, the gloss, moisture and combability of the dyed hair were evaluated by 10 female panelists as in Example 18
Based on the same evaluation criteria as in the above, a five-step evaluation was performed. The results are shown in Table 14 as an average value of 10 persons. (Hair strength and cysteic acid content) For each of the hair bundles after the sensory evaluation, the tensile strength of the hair was measured in the same manner as in Example 20. Further, a part of the hair after the hair dyeing treatment was used,
The amount of cysteic acid (μmol / g) was measured in the same manner as in Example 1. Table 14 shows the results (average values).

[0061]

[Table 14]

As shown in Table 14, the hair dye containing the 2-amino-2-methyl-1,3-propanediol salt of the condensate of the non-hydroxylanolin fatty acid and the silk protein-derived peptide of Example 21 was used. The hair that has been subjected to the hair dyeing treatment is superior to the hair treated with the hair dye of Comparative Example 21 or Comparative Example 22 in any of the evaluation items of gloss, moisture, and combability, and furthermore, the hair is pulled. High strength,
Low cysteic acid content in hair. This result also indicates that the 2-amino-2-methyl-1,3-propanediol salt of an acylated peptide obtained by condensing a non-hydroxylanolin fatty acid with a silk protein-derived peptide imparts gloss and moisture to hair. It is excellent in the action of improving the combability of hair and the action of improving the combability of hair, and is also excellent in the action of preventing hair damage during hair dyeing treatment and increasing the tensile strength of hair.

Example 22 and Comparative Examples 23 to 24 Three types of body shampoos having the compositions shown in Table 15 were prepared, the body was washed with each of the body shampoos, and the smoothness and moisture of the washed skin were evaluated. In Example 22, a triethanolamine salt of a condensate of a non-hydroxylanolin fatty acid synthesized in Example 4 and a wheat protein-derived peptide was added as an acylated peptide to the composition. In Comparative Example 23, a triethanolamine salt of a condensate of isostearic acid and a wheat protein-derived peptide synthesized in Comparative Example 3 was used instead of a triethanolamine salt of a condensate of a non-hydroxylanolin fatty acid and a wheat protein-derived peptide. Was added to the material. In Comparative Example 24, the acylated peptide or a salt thereof was not added to the composition.

[0064]

[Table 15]

Evaluation method: Each body shampoo shown in Table 15 was used for 3 days by panelists of 5 men and 5 women without displaying the contents, and the smoothness and moisture of the skin after use were evaluated. . Evaluation criteria are the best (2
Points), next good (1 point), bad (0 points)
Evaluation was made based on the average value of 10 persons. Table 16 shows the results.

[0066]

[Table 16]

As shown in Table 16, all the panelists showed that the body shampoo containing the triethanolamine salt of the condensate of the non-hydroxylanolin fatty acid and the wheat protein-derived peptide of Example 22 was smooth on the washed skin. They say that the action of giving hydration is superior to the body shampoos of Comparative Examples 23 and 24. This result indicates that the triethanolamine salt of an acylated peptide obtained by condensing a non-hydroxylanolin fatty acid with a wheat protein-derived peptide has an excellent effect of giving smoothness and moisture to the skin after washing, and that it is an isostearic acid and wheat This shows that the acylated peptide is superior to the triethanolamine salt of an acylated peptide obtained by condensing with a protein-derived peptide.

Example 23 and Comparative Examples 25 to 26 Three types of hand and nail creams having the compositions shown in Table 17 were prepared, and each was applied to the washed hands, and the gloss, moisture and smoothness of the skin were evaluated. . In Example 23, as an acylated peptide or a salt thereof, a sodium salt of a condensate of a non-hydroxylanolin fatty acid synthesized in Example 3 and a keratin-derived peptide was added to the composition. In Comparative Example 25, Comparative Example 2 was used instead of the sodium salt of the condensate of the non-hydroxylanolin fatty acid and the keratin-derived peptide.
The sodium salt of a condensate of the lanolin fatty acid and the keratin-derived peptide synthesized in the above was added to the composition. Comparative Example 26
Did not add the acylated peptide or salt thereof to the composition.

[0069]

[Table 17]

Evaluation method: A panel of 5 men and 5 women was washed with 20% coconut oil fatty acid potassium soap aqueous solution and washed with water, and each hand & nail cream in Table 18 was measured in a 1 ml measuring spoon. 1 cup (approximately 1
g) was evenly spread over the back of the hand and rubbed, and the smoothness, moisture, and luster of the skin after application were evaluated in three steps according to the same evaluation criteria as in Example 22. The results are shown in Table 18 as the average value of 10 persons.

[0071]

[Table 18]

As shown in Table 18, almost all of the panelists applied the hand and nail cream containing the sodium salt of the condensate of the non-hydroxylanolin fatty acid and the keratin-derived peptide of Example 23 to the skin after application. Smoothness,
They answered that the action of imparting moisture and luster was superior to the hand and nail creams of Comparative Examples 25 and 26.
This result indicates that the sodium salt of the acylated peptide obtained by condensing the non-hydroxylanolin fatty acid and the keratin-derived peptide is excellent in the effect of imparting smoothness, moisture, and luster to the washed skin, and that the comparative example 2 This shows that the lanolin fatty acid is superior to the sodium salt of an acylated peptide obtained by condensing a keratin-derived peptide.

As described in detail above, the cosmetic for hair containing the acylated peptide obtained by condensing the non-hydroxylanolin fatty acid of the present invention with the protein-derived peptide obtained by hydrolyzing the protein or a salt thereof is used for hair. In addition to imparting a moist feeling, luster, moisture and the like, it has an effect of remarkably suppressing damage caused by chemical treatment such as permanent treatment of hair. In addition, the cosmetic for skin containing an acylated peptide or a salt thereof obtained by condensing the non-hydroxylanolin fatty acid and the protein-derived peptide obtained by hydrolyzing a protein of the present invention exhibits a protective effect on the skin and a moisturizing effect. Gives an excellent feeling of use such as smoothness and moisture.

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁶ Identification code FI A61K 7/09 A61K 7/09 7/13 7/13 7/48 7/48 7/50 7/50 C07K 14/415 C07K 14 / 415 14/435 14/435 14/47 14/47 (72) Inventor Masato Yoshioka 1-2-14 Fukuichicho, Higashiosaka-shi, Osaka Co., Ltd.Seiwa Kaseinai Co., Ltd. (72) Inventor Sueko Kobayashi Osaka Prefecture Seiwa Kaseinai Co., Ltd. 1-2-14 Fukuichicho, Higashiosaka City

Claims (6)

[Claims] 1. A protein-derived peptide obtained by hydrolyzing a protein, 30 to 45% by weight of an iso-type fatty acid having 10 to 31 carbon atoms, 30 to 50% by weight of an anteiso-type fatty acid having 11 to 31 carbon atoms, and It contains 10 to 30% by weight of a normal fatty acid having 10 to 30 carbon atoms, and the total amount of the iso-fatty acid and the anteiso-fatty acid is at least 6%.
0% by weight, and the content of hydroxy fatty acid is 10%.
An acylated peptide or a salt thereof obtained by condensing lanolin-derived non-hydroxy fatty acid in an amount of less than 10% by weight. 2. A protein-derived peptide obtained by hydrolyzing a protein, 30 to 45% by weight of an iso-type fatty acid having 10 to 31 carbon atoms, 30 to 50% by weight of an anteiso-type fatty acid having 11 to 31 carbon atoms, and It contains 10 to 30% by weight of a normal fatty acid having 10 to 30 carbon atoms, and the total amount of the iso-fatty acid and the anteiso-fatty acid is at least 6%.
0% by weight, and the content of hydroxy fatty acid is 10%.
A cosmetic containing an acylated peptide or a salt thereof obtained by condensing lanolin-derived non-hydroxy fatty acid in an amount of less than 10% by weight. 3. The cosmetic according to claim 2, wherein the average number of carbon atoms of the iso-type fatty acid, anteiso-type fatty acid and normal-type fatty acid in the lanolin-derived non-hydroxy fatty acid is 15 to 24. 4. The cosmetic according to claim 2, wherein the average carbon number of the iso-type fatty acid, the anteiso-type fatty acid and the normal-type fatty acid in the lanolin-derived non-hydroxy fatty acid is 17 to 22. 5. The lanolin-derived non-hydroxy fatty acid having a content of isoform fatty acid having 10 to 31 carbon atoms of 30 to 35.
3. The composition of claim 2, wherein the content of the anteiso fatty acid having 11 to 31 carbon atoms is 35 to 45 wt% and the content of the normal fatty acid having 10 to 30 carbon atoms is 12 to 16 wt%. 5. The cosmetic according to items 4 to 4. 6. The cosmetic according to claim 2, wherein the protein-derived peptide is selected from a collagen-derived peptide, a keratin-derived peptide, a silk protein-derived peptide, a casein-derived peptide, a soybean protein-derived peptide, and a wheat protein-derived peptide. Fees.