JPH05124936A - Hair cosmetic - Google Patents

Abstract

PURPOSE:To provide a cosmetic having a combination of hair conditioning effect and hair trimming effect. CONSTITUTION:The objective hair cosmetic excellent in both hair conditioning and hair trimming effects, contains, as essential ingredients (A) pref. 0.1-20 (esp. 0.5-10)wt.% of a siloxane derivative of formula I (R<1>-R<3> are such that at least one of them is formula II and/or formula III, the rest being 1-4C alkyl; R<4> is 1-4C alkyl; R<5> and R<6> are such that one of them is H, the other being 6-30C straight, branched or cyclic alkyl, alkenyl or hydroxyalkyl; (m) and (n) satisfy the relationship: m+n=1-200) (e.g. a compound of formula IV) and (B) pref. 0.05-10(esp. 0.1-5)wt.% of a film-forming polymer, e.g. polyvinylpyrrolidone-, acidic vinyl ether-, acidic polyvinyl acetate-, or acrylic(acidic, amphoteric or basic)-based polymeric compound.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a hair cosmetic composition containing a siloxane derivative and a film-forming polymer, which is excellent in hair conditioning and styling effects.

[0002]

2. Description of the Related Art Conventionally, the problems to be solved by the invention
For the purpose of adjusting the conditioning of hair such as comb street,
Oil components such as silicone oil, ester oil, hydrocarbon oil,
Hair cosmetics containing a cationic activator and a protein hydrolyzate are used.

However, these hair cosmetics have not satisfied both the conditioning effect and the hair styling effect.

[0004] Therefore, there has been a demand for a hair cosmetic having both a conditioning effect and a hair styling effect.

[0005]

Under such circumstances, as a result of intensive studies, the present inventors have found that, when a specific siloxane derivative and a film-forming polymer are used, a hair makeup having both a hair conditioning effect and a hair styling effect. The present invention has been completed by finding that a charge can be obtained.

That is, the present invention provides the following components (a) and (b) (a) a siloxane derivative represented by the general formula (1).

[0007]

[Chemical 2]

[Wherein at least one of R ¹ , R ² and R ³ is of the formula: —CH ₂ CH ₂ CH ₂ OCH ₂ CH (OR ⁶ ) CH ₂ OR ⁵ or —CH ₂ CH ₂ CH ₂ OCH (CH ₂ OR ⁵ ) CH ₂ OR ⁵ (One of R ⁵ and R ⁶ represents a hydrogen atom, and the other is a linear, branched or cyclic alkyl group, alkenyl group or hydroxyalkyl group having 6 to 30 carbon atoms. Is a substituent represented by R ¹ , R ² and R ³ and R other than the above.
⁴ represents an alkyl group having 1 to ⁴ carbon atoms, m and n are m +
n represents a number of 1 to 200] (b) A hair cosmetic comprising: a film-forming polymer.

The siloxane derivative (1) of the component (a) used in the present invention can be produced by a conventional method. For example, as shown in JP-A-2-265926, a platinum catalyst of a platinum catalyst can be prepared according to the following reaction formula. It is produced by subjecting siloxane (2) to allyl glyceryl ether (3) or (4) in the presence of hydrosilylation reaction.

[0010]

[Chemical 3]

(In the formula, at least one of R ⁷ , R ⁸ and R ⁹ represents a hydrogen atom, the rest represent an alkyl group having 1 to 4 carbon atoms, and R ⁷ , R ⁸ , R ⁹ , m and n has the same meaning as above)

As the siloxane used in the above reaction, for example, pentamethyldisiloxane, heptamethyltrisiloxane, nonamethyltetrasiloxane, undecamethylpentasiloxane, tridecamethylhexasiloxane, tetramethyldisiloxane, hexamethyltrisiloxane. , Octamethyltetrasiloxane, decamethylpentasiloxane, dodecamethylhexasiloxane and other relatively short chain length polysiloxanes,
Polysiloxanes having a long chain length up to a molecular weight of about 15,000 can be used as long as they have m + n of 1 to 200 and contain at least one Si-H group in the molecule.

The allyl glyceryl ether (3) or (4) is obtained by reacting the glycidyl ethers (5) with allyl alcohol in the presence of a Lewis acid catalyst or a base catalyst, for example, according to the following reaction formula: It can be easily manufactured.

[0014]

[Chemical 4]

(In the formula, R ¹⁰ represents a linear, branched or cyclic alkyl group, alkenyl group or hydroxyalkyl group having 6 to 30 carbon atoms)

As the glycidyl ether (5),
For example, n-hexyl glycidyl ether, n-octyl glycidyl ether, n-decyl glycidyl ether,
saturated linear aliphatic glycidyl ethers such as n-dodecyl glycidyl ether, n-tetradecyl glycidyl ether, n-hexadecyl glycidyl ether, and n-octadecyl glycidyl ether; 2-ethylhexyl glycidyl ether, 2-hexyl decyl glycidyl ether, 2- Heptyl undecyl glycidyl ether, 2-
Octyl dodecyl glycidyl ether, 2-decyl tetradecyl glycidyl ether, 5,7,7-trimethyl-2- (1,3,3-trimethylbutyl) octyl glycidyl ether, the following formula

[0017]

[Chemical 5]

A saturated branched aliphatic glycidyl ether such as methyl-branched isostearyl glycidyl ether represented by the formula (wherein p + q = 14 and a distribution having p = q = 7 at the top); cyclohexylglycidyl ether, cyclo Heptyl glycidyl ether, cyclooctyl glycidyl ether, cyclododecyl glycidyl ether,
Cyclic aliphatic glycidyl ethers such as abiethyl glycidyl ether, dihydroabietyl glycidyl ether, tetrahydroabietyl glycidyl ether, cholesteryl glycidyl ether, cholestanyl glycidyl ether; unsaturated fatty acids such as 9-octadecenyl glycidyl ether, farnesyl glycidyl ether Group glycidyl ethers; and hydroxyalkyl glycidyl ethers such as 12-hydroxystearyl glycidyl ether.

In the hair cosmetic composition of the present invention, the siloxane derivative (1) is preferably added in an amount of 0.1 to 20% by weight (hereinafter simply referred to as%), particularly 0.5 to 10% in the total composition.

Examples of the film-forming polymer as the component (b) include polyvinylpyrrolidone-based polymer compounds,
An acidic vinyl ether polymer compound, an acidic polyvinyl acetate polymer compound, an acidic acrylic polymer compound, an amphoteric acrylic polymer compound, a basic acrylic polymer compound or the like can be used.

As the polyvinylpyrrolidone-based polymer compound, for example, Luviskol K12, 17, 30,
60, 80, 90 (above, manufactured by BASF), PVP K
Polyvinylpyrrolidone such as 15, 30, 60, 90 (all manufactured by GAF); Luviskol VA28, 3
7, 55, 64, 73 (above, manufactured by BASF), PVP
/ VA E-735, E-635, E-535, E-3
35, S-630, W-735 (above, manufactured by GAF) and the like; polyvinylpyrrolidone / vinyl acetate copolymer; Luv
Polyvinylpyrrolidone / vinyl acetate / vinyl propionate terpolymer such as iskol VAP343 (manufactured by BASF); Luviflex (manufactured by BASF), COP
OLYMER 845, 937, 958 (above, GAF
Polyvinylpyrrolidone / alkylamino acrylate copolymers such as manufactured by Luviflex VBM 35
(Manufactured by BASF) polyvinylpyrrolidone / acrylate / (meth) acrylic acid copolymer; COPOLYME
Examples thereof include polyvinylpyrrolidone / alkylaminoacrylate / vinylcaprolactam copolymers such as RVC-713 (all manufactured by GAF).

Examples of the acidic vinyl ether type polymer compound include GANTREZ ES-225 and ES-42.
5, and a vinyl vinyl ether / alkyl maleic anhydride half ester copolymer such as SP-215 (all manufactured by GAF).

Examples of acidic polyvinyl acetate-based polymer compounds include RESIN 28-1310 (National Stains).
rch), Luviset CA66 (manufactured by BASF) and other vinyl acetate / crotonic acid copolymers; RESIN
28-2930 (National Starch) vinyl acetate / crotonic acid / vinyl neodecanoate copolymer; Lu
vinyl acetate such as viset CAP (manufactured by BASF)
Examples include crotonic acid / vinyl propionate copolymer.

Examples of the acidic acrylic polymer compound include (meth) acrylic acid / (meth) acrylic acid esters such as plus size L53P (manufactured by Kyosho Chemical Co., Ltd.) and Diahold (manufactured by Mitsubishi Yuka Co., Ltd.). Copolymer; Ultr
ahold 8 (manufactured by BASF), AMPHOMER
Examples thereof include acrylic acid / acrylic acid alkyl ester / alkyl acrylamide copolymers such as V-42 (manufactured by National Starch).

Examples of the amphoteric acrylic polymer compound include Yuka Former M-75 and SM (Mitsubishi Yuka Co., Ltd.).
AMPHOMER 28-49; dialkylaminoethyl (meth) acrylate / (meth) acrylic acid alkyl ester copolymer;
10 (manufactured by National Starch) and the like, such as hydroxypropyl acrylate / butylaminoethyl methacrylate / octylamide acrylate copolymer.

As the basic acrylic polymer compound,
For example, an acrylamide / acrylic ester type quaternary copolymer described in JP-A-2-180911 can be used.

In the hair cosmetic composition of the present invention, these film-forming polymers account for 0.05 to 10%, especially 0.1 to 10%, based on the total composition.
It is preferable to add 5%.

Further, in the hair cosmetic composition of the present invention, in addition to the above-mentioned essential components, cosmetic components that are usually used, such as anionic activators, nonionic activators, cationic activators, amphoteric activators, etc., can be used as required. Surfactants; ester oils, waxes, wax esters, hydrocarbons, silicones and their derivatives, polyoxyalkylene derivatives, polyoxyalkylene alkyl ether derivatives, higher alcohols and other oil agents; water, lower alcohols and other volatile carriers; LP
Propellants such as liquefied gases such as G, CFCs and DME, and compressed gases such as carbon dioxide and nitrogen; other protein derivatives, plant extracts such as crude drugs, water-soluble polymer substances, sequestering agents,
Preservatives, bactericides, moisturizers such as glycerin, pH adjusters, ultraviolet absorbers, antioxidants, oxidizing agents, reducing agents, dyes, and fragrances can be added within the range that does not impair the effects of the present invention.

The hair cosmetic composition of the present invention can be produced by mixing the siloxane derivative (1) and the film-forming polymer according to a usual method, and can be used in shampoos, hair foams, conditioners, hair tonics, setting agents and the like. Although it can be made into a dosage form, a setting agent is particularly preferable.
It is preferable to use a propellant when forming a hair foam or a hair spray, and to use a double-structured container when forming a pump spray.

[0030]

The hair cosmetic composition of the present invention is excellent in both hair conditioning effect and hair styling effect.

[0031]

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. Reference example 1

[0032]

[Chemical 6]

Synthesis of 1- (4,8-dioxa-6-hydroxytetradecyl) -1,1,3,3,3-pentamethyldisiloxane [compound (a)]: (1) 3-allyloxy-1 -Hexyloxy-2-propanol; To 290 g of allyl alcohol, under a nitrogen atmosphere, slowly add 1.15 g of metallic sodium carefully and dissolve,
After heating to 60 ° C., 79 g of hexyl glycidyl ether was slowly added dropwise over about 80 minutes. After the dropping was completed, stirring was continued at 60 ° C. for another 4.5 hours. After distilling off unreacted allyl alcohol from the reaction mixture, 500 ml of ether was added,
It was repeatedly washed with saturated saline until the aqueous layer became neutral.
The ether layer was dried over anhydrous sodium sulfate, the ether was distilled off, and the residue was distilled under reduced pressure to give 99 g of 3-allyloxy-1-hexyloxy-2-propanol (yield 88
%) Was obtained. (2) Compound (a); 3-allyloxy-1 obtained in (1)
-Hexyloxy-2-propanol 28 g (0.13 mol),
Pentamethyldisiloxane 14.8 g (0.10 mol), 10% potassium acetate ethanol solution 2 ml and isopropyl alcohol 100 ml as a solvent were stirred at room temperature under H ₂ PtCl ₆・ 6.
It was added H ₂ 0 2% isopropyl alcohol solution 1 ml. The reaction mixture was warmed to 50 ° C. and stirred for 2 hours, then
Insoluble matter was removed by filtration, and the filtrate was concentrated to recover the crude product.
40 g was obtained. This was purified by flash column chromatography (silica gel 800 g, developing solvent; hexane: ethyl acetate = 3: 1), and compound (a) 11.8 g (yield 32
%) Was obtained.

Reference Example 2

[0035]

[Chemical 7]

1,9-bis (4-oxa-6-hydroxy-7-methylheptadecyloxyheptyl) -1,1,
Synthesis of 3,3,5,5,7,7,9,9-decamethylpentasiloxane [compound (b)]: (1) 3-allyloxy-1-methylheptadecyloxy-
2-propanol; in Reference Example 1 (1), 32.7 g of methyl-branched isostearyl glycidyl ether (0.01 mol
) And 58 g (1.0 mol) of allyl alcohol and 33.4 g (0.087 mol, yield) of 3-allyloxy-1-methylheptadecyloxy-2-propanol.
87%). (2) Compound (b): In Reference Example 1 (2), 12.5 g of 3-allyloxy-1-methylheptadecyloxy-2-propanol obtained in (1) above and 13.8 g of decamethylpentasiloxane (0.20 mol) Compound (b) (14.6 g, yield 68%) was obtained in substantially the same manner except that the compound (b) was used.

Reference Example 3

[0038]

[Chemical 8]

1- (4-oxa-6-hydroxy-7-
Tetrahydroabietyloxyheptyl) -1,1,
3,3,5,5,7,7,9,9,11,11,13,
Synthesis of 13,15,15,17,17,17,17-nonadecamethylnonasiloxane [compound (c)]: (1) 3-allyloxy-1-tetrahydroabietyloxy-2-propanol; Reference Example 1 (1) At 52.3 g of tetrahydroabiethyl glycidyl ether (0.15
mol) and allyl alcohol 174 g (3.0 mol) were used in the same manner as described above, and 3-allyloxy-1-tetrahydroabietyloxy-2-propanol 48.6 g (0.11
9 mol, yield 80%) was obtained. (2) Compound (c); 3-allyloxy-1 obtained in (1)
-Tetrahydroabiethyloxy-2-propanol
9.8 g (0.024 mol), 1,1,3,3,5,5,7,
7,9,9,11,11,13,13,15,15,1
13.3g of 17,17,17-nonadecamethylnonasiloxane
(0.02mol), 10% potassium acetate ethanol solution 0.47g
While stirring 60 ml of isopropyl alcohol at room temperature, 1.2 g of a 2% isopropyl alcohol solution of H ₂ PtCl ₆ .6H ₂ O as a catalyst was added. The reaction mixture was heated to 40 ° C. and stirred for 20 hours, the solvent was evaporated under reduced pressure, and the catalyst was removed by silica gel short column chromatography. Then, under reduced pressure, excess 3-allyloxy-1-
Tetrahydroabietyloxy-2-propanol was distilled off, and the residue was purified again by silica gel short column chromatography to give 11.0 g of compound (c).
(Yield 51%) was obtained.

Reference Example 4

[0041]

[Chemical 9]

Synthesis of 1- (4,7-dioxa-6-hydroxymethylpentacosa) -1,1,3,3,3-pentamethyldisiloxane [compound (d)]: (1) 1-allyloxy- 3-benzyloxy-2-octadecyloxypropane; allyl alcohol 232g (4.0mo
l), in a nitrogen atmosphere, sodium 1.9 g (0.08 mol)
) Was slowly and carefully added to dissolve it, and the mixture was heated to 60 ° C., and then 65.7 g (0.40 mol) of benzyl glycidyl ether was added dropwise over about 30 minutes. After the dropping was completed, stirring was continued at 60 ° C. for another 5 hours. After unreacted allyl alcohol was distilled off from the reaction mixture, 500 ml of ether was added, and the mixture was repeatedly washed with saturated saline. The ether layer was dried over anhydrous sodium sulfate, the ether was distilled off, and the residue was distilled under reduced pressure to obtain 63.0 g of 1-allyloxy-3-benzyloxy-2-propanol (yield 71%). 31 g (0.1%) of the obtained 1-allyloxy-3-benzyloxy-2-propanol.
14mol) and toluene 500ml, potassium hydroxide (granular) 30g and octadecyl chloride 48.5g (0.17mol)
) Was added and the mixture was heated under reflux under azeotropic dehydration for 5 hours. After repeatedly washing the organic layer with water, toluene was distilled off. 43.1 g (0.112 mol, 80% yield) of 1-allyloxy-3-benzyloxy-2-octadecyloxypropane by purifying using a silica gel short column
Got (2) Compound (d); 1-allyloxy-3-benzyloxy-2-octadecyloxypropane 40 obtained in (1)
g (0.105 mol) and pentamethyldisiloxane 14 g (0.
A small amount of H ₂ PtCl ₆ .4H ₂ O was directly added to the mixture (10 mol) and the mixture was stirred at room temperature for about 30 minutes. After diluting the reaction mixture with 200 ml of hexane, a silica gel short column (silica gel 150 g, developing solvent; hexane: ethyl acetate = 10:
The origin was removed in 1). By distilling off the solvent,
38.7 g of crude product was obtained. Then, add this to methanol 500
ml and 10% Pd-C 1.7g, and hydrogen gas 19ml at room temperature
It was introduced for 14 hours at a speed of / min. After removing the catalyst by filtration and distilling off methanol from the filtrate, flash column chromatography (silica gel 800 g, developing solvent;
Purification using hexane: ethyl acetate = 12: 1) gave 18.7 g (0.035 mol, yield 35%) of compound (d).

Reference Example 5

[0044]

[Chemical 10]

1- (4-oxa-6-hydroxy-7-
Methylheptadecyloxyheptyl) -1,1,3,3,3
Synthesis of 5,5,7,7,9,9,9-undecamethylpentasiloxane [Compound (e)]: In the same manner as in Reference Example 2 (2) except that 9.0 g of undecamethylpentasiloxane was used. 11.0 g of compound (e) (yield 59
%) Was obtained.

Reference Example 6

[0047]

[Chemical 11]

Α, ω-bis {4-oxa-6-hydroxy-7- [5,7,7-trimethyl-2- (1,3,3
Synthesis of -trimethylbutyl) octyloxy] heptyl} -dimethylpolysiloxane [compound (f)]: In Reference Example 3, 3-allyloxy-1 was used instead of 3-allyloxy-1-tetrahydroabiethyloxy-2-propanol. -{5,7,7-trimethyl-2- (1,3,
3-trimethylbutyl) octyloxy} -2-propanol was used in substantially the same manner as in the case of using compound (f) 3
3.38 g (yield 83%) was obtained.

Reference Example 7

[0050]

[Chemical 12]

Synthesis of α, ω-bis (4-oxa-6-hydroxy-7-tetraabiethyloxyheptyl) -dimethylpolysiloxane [compound (g)]: Reference Example 3
In (2), α, ω-dihydrogendimethylpolysiloxane

[0052]

[Chemical 13]

Compound (g) 32.5 g (yield 65%) was obtained in substantially the same manner except that was used.

Example 1 A hair lotion having the following composition was produced by a conventional method. Compound (a) 5 (%) Acrylic acid / acrylic acid ester copolymer (Plus size L-53P, manufactured by Kyowa Chemical Co., Ltd.) 0.5 Perfume 0.3 Ethyl alcohol Suitable amount

Example 2 A jet hair lotion having the following composition was produced by a conventional method. Compound (b) 15 (%) Polyvinylpyrrolidone (PVP K-30, manufactured by GAF) 0.1 Fragrance Liquefied petroleum gas Appropriate amount Dimethyl ether 25

Comparative Example 1 A hair lotion having the following composition was produced by a conventional method. Dimethylpolysiloxane (5000cs) 5 (%) Acrylic acid / acrylic acid ester copolymer (Plus size L-53P, manufactured by Mutual Chemical) 0.5 Fragrance 0.3 Ethyl alcohol Suitable amount

Comparative Example 2 A jet hair lotion having the following composition was produced by a conventional method. Isoparaffin (Isosol 400, manufactured by Nippon Petrochemical Co., Ltd.) 15 (%) Polyvinylpyrrolidone (PVP K-30, manufactured by GAF) 0.5 Perfume Trace amount of liquefied petroleum gas Dimethyl ether 25

Test Examples The hair cosmetics obtained in Examples 1 and 2 and Comparative Examples 1 and 2 were examined for hair styling effect, combing and sticky feeling.
The results are shown in Table 1. (Test method) Each sample was applied to a hair bundle of 20 g and sensory-evaluated according to the following criteria. Comb path: Good comb / brush path ○ Good comb / brush path △ Comb / brush path is poor x Sticky feeling: No sticky feeling ○ Slight sticky feeling △ Slight sticky feeling × Hair styling effect : Hair bundles have cohesiveness ○ Hair bundles have slightly cohesiveness △ Hair bundles have no cohesiveness ×

[0059]

[Table 1]

Example 3 Shampoo: A shampoo having the following composition was produced by a conventional method. Sodium polyoxyethylene lauryl ether sulfate 64.0 (%) Lauric acid diethanolamide 3.0 Acrylamide / acrylic ester type quaternary copolymer (Japanese Patent Laid-Open No. 2-180911, Synthesis Example 1) 0.2 Cationic polymer (Polymer JR-400, UCQ) 0.1) Compound (c) 0.5 Sodium benzoate 0.8 Perfume Trace amount of purified water Appropriate amount

Example 4 Hair Foam: A hair foam having the following composition was produced by a conventional method. Acrylic acid / Acrylic ester copolymer (Plus size L-53P, manufactured by Kyowa Chemical Co., Ltd.) 3.4 (%) Compound (d) 10.0 Ethyl alcohol 9.8 Stearyl trimethyl ammonium chloride 0.5 2-Amino-2-methyl-1-propanol Trace fragrance 0.1 LPG 10.0 Purified water Suitable amount

Example 5 Conditioner: A conditioner having the following composition was produced by a conventional method. Amphoteric polymer (Yukaformer SM, manufactured by Mitsubishi Yuka) 0.5 (%) Cetyl trimethyl ammonium chloride 2.0 Hydroxyethyl cellulose 0.5 Compound (e) 0.5 Propylene glycol 5.0 Cetanol 3.0 Perfume 0.3 Purified water Suitable amount

Example 6 Aerosol Spray: An aerosol spray having the following composition was produced by a conventional method. Compound (f) 10.0 (%) Amphoteric polymer (Yukaformer AM-75, manufactured by Mitsubishi Yuka) 2.0 Dimethyl ether 5.0 Perfume 0.2 LPG 40.0 Ethanol Suitable amount

Example 7 Pump Spray: A pump spray having the following composition was produced by a conventional method. Polyvinylpyrrolidone (PVP K-90, GAF) 0.1 (%) Compound (f) 3.0 Ethanol 10.0 Fragrance 0.3 Purified water Suitable amount

Example 8 Hair Tonic: A hair tonic having the following composition was produced by a conventional method. Polyvinylpyrrolidone / alkylaminoacrylate copolymer (Copolymer 845, manufactured by GAF) 0.1 (%) Octopirox 0.5 Ethanol 40.0 Compound (g) 1.0 Perfume 0.2 Purified water Suitable amount

Claims (1)

[Claims] 1. The following components (a) and (b) (a) a siloxane derivative represented by the general formula (1): [In the formula, at least one of R ¹ , R ² and R ³ has the following formula: -CH ₂ CH ₂ CH ₂ OCH ₂ CH (OR ⁶ ) CH ₂ OR ⁵ or -CH ₂ CH ₂ CH ₂ OCH (CH ₂ OR ⁵ ) CH ₂ OR ⁵ (one of R ⁵ and R ⁶ represents a hydrogen atom, and the other represents a linear, branched or cyclic alkyl group, alkenyl group or hydroxyalkyl group having 6 to 30 carbon atoms) The substituents represented are represented by R ¹ , R ² and R ³ and R other than the above.
⁴ represents an alkyl group having 1 to ⁴ carbon atoms, m and n are m +
n represents a number of 1 to 200] (b) A hair cosmetic containing a film-forming polymer.