JPH1029916A - Cosmetic material for hair - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a cosmetic material which is useful for application to hair as a hair treatment and the like excellent in smoothness, pliability, moisture- holding capacity, giving good feeling, protection from external simulation and fixation of an active ingredient by formulating a specific component thereto. SOLUTION: This objective cosmetic material for hair contains a modified polysiloxane of formula I R<1> and R<2> are each an 1-6C alkyl and an 6-10C aromatic hydrocarbon; R<3> is a 16-600C saturated hydrocarbon; (n) is an average value of 0-3,000}. The compound of formula I is preferably formulated at the ratio of 0.1-20wt.% in the cosmetic material. Cationic surfactants, particularly quaternary ammonium salts of formula II one or two of R<4> -R<7> are each an 8-27C alkyl and a 8-28C hydroxyalkyl; X is a halogen and an organic anion} are preferably formulated additionally at the ratio of 0.5-5wt.% in the cosmetic material.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a hair cosmetic,
Specifically, when applied to hair, it is specified as a component for expressing effects such as imparting smoothness, flexibility, moisturizing properties and good feel, protection from external stimuli, and improving the fixability of active ingredients. The present invention relates to a hair cosmetic containing a modified polysiloxane and having the above-mentioned effects and excellent durability.

[0002]

2. Description of the Related Art Conventionally, hair in which a cationic surfactant is combined with an oil such as a higher alcohol, glyceride, liquid paraffin, or an ester to impart flexibility, smoothness, and antistatic property to the hair. Cosmetics are used. In this case, by using these oil agents, the flexibility and smoothness of the hair can be improved as compared with the case where the cationic surfactant is used alone. However, there is a disadvantage that a feeling of residual oil agent, that is, an oily feeling cannot be avoided.

[0003] Compared with the above-mentioned oils, silicone compounds such as polydimethylsiloxane which can impart more excellent properties to hair in terms of smoothness, lubricity, crisp feel and glossiness are widely used in hair cosmetics. Is being done. However, since the silicone compound has insufficient compatibility with water and other oil agents, there has been a problem that the stability of the hair cosmetic during preparation and storage becomes insufficient.

Accordingly, a hair cosmetic in which a high molecular weight silicone oil is dissolved in a low boiling point oil and emulsified into a W / O type has been proposed (Japanese Patent Application Laid-Open No. 3-157317). Silicone oil has a feature that it spreads easily on the hair surface due to its low surface tension, but has the disadvantage that it has a strong squeaky feeling when the hair is wet and has insufficient adhesion to the hair.

[0005] Many hair cosmetics have also been proposed in which modified silicone compounds such as amino-modified silicone and polyether-modified silicone are blended to improve the compoundability and the adsorptivity to hair. The feeling of squeaking is not sufficiently improved, and the increased water-solubility results in insufficient sustainability, resulting in insufficient moisturizing effect when the hair is dried, and a lack of moist feeling.

Accordingly, the squeaky feeling, which is a disadvantage of silicones, is improved, and excellent characteristics (smoothness,
It has been desired to develop a hair cosmetic which has flexibility, gloss, etc.) and has a long-lasting fixability to the hair surface.

[0007]

SUMMARY OF THE INVENTION An object of the present invention is to provide smoothness, flexibility, moisturizing properties and good feel when applied to hair, protection from external stimuli, and fixing properties of active ingredients. It is an object of the present invention to provide a hair cosmetic which has an effect of improving and has excellent durability of these effects.

[0008]

Means for Solving the Problems The present inventors have conducted intensive studies in view of such circumstances, and as a result, have found that a hair cosmetic containing a specific polysiloxane can solve the above-mentioned problems. Was completed. That is, the present invention provides a hair cosmetic comprising the modified polysiloxane represented by the general formula (I).

[0009]

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[Wherein, R ¹ and R ² may be the same or different and each is an alkyl group having 1 to 6 carbon atoms or an aromatic group having 6 to 10 carbon atoms which may be substituted by an alkyl group. Shows a hydrocarbon group. However,
The (n + 2) R ¹ groups and the (n + 2) R ² groups may be the same or different. R ³ represents a linear or branched saturated hydrocarbon group having an average carbon number of 16 to 600. However, the two R ³ groups may be the same or different. n: The average value shows the number of 0-3000. ]

[0011]

Embodiments of the present invention will be described below in detail.

In the general formula (I), among the groups represented by R ¹ and R ² , the alkyl group having 1 to 6 carbon atoms includes
Methyl group, ethyl group, propyl group, isopropyl group, n
-Butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group and the like. Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted with an alkyl group include a phenyl group, a methylphenyl group, and a naphthyl group. R ¹ and R ² are particularly preferably a methyl group and a phenyl group. These R ¹ and R ² may be the same or different for each repeating unit.

In the general formula (I), the linear or branched saturated hydrocarbon group represented by R ³ has an average carbon number of 16 to 16.
It is 600, preferably 30 to 300, more preferably 40 to 300. When the average carbon number is less than 16, the composition becomes oily, and sufficient effect persistence cannot be obtained, resulting in a sticky feeling. Further, the compatibility with hydrocarbon oils, surfactants, and the like deteriorates, which is not preferable. On the other hand, if it exceeds 600, it becomes resinous, and the compoundability of the product deteriorates.

Among such hydrocarbon groups, examples of the branched chain include those having a short-chain branch having 1 to 5 carbon atoms at the fifth carbon atom counted from the terminal carbon atom of the saturated hydrocarbon group. be able to. In this case, examples of the short-chain branch include a 2-methyl group, a 3-methyl group, and a 2,2-dimethyl group. When the chain has such a short-chain branch, and when the chain length of the saturated hydrocarbon group is short, the melting point of the modified polysiloxane represented by the formula (I) can be increased without affecting other physical properties at all. Can be reduced.

In the above general formula (I), n has an average value of 0 to 300.
Although the number is 0, a number having an average value of 100 to 3000 is preferable. This is because when n is 100 or more, smoothness and flexibility are further improved. As for the compoundability depending on the viscosity of the compound, n is preferably 3000 or less. For similar reasons, n
Is more preferably a number having an average value of 200 to 2,000.

Furthermore, in the above general formula (I), is not particularly limited to the ratio of the polysiloxane moiety remaining two saturated hydrocarbon group moiety represented by R ^3, the two represented by R ³ saturated hydrocarbons The weight ratio of the sum of the hydrogen group portions to the remaining polysiloxane portion is preferably 30:70 to 1:99, and 20:80 to 2:98.
Is more preferred. When the weight ratio of the sum of the two saturated hydrocarbon groups represented by R ³ is 30% by weight or less, a smooth feel (smoothness) peculiar to silicone is obtained, and the oily feeling seen in hydrocarbon oils is obtained. Less stickiness is preferred. Further, when the weight ratio of the sum of the two saturated hydrocarbon groups represented by R ³ is 1% by weight or more, the crystallinity of the R ³ increases, so that the stickiness is suppressed and the pour point (melting point) , The duration of the effect increases, which is preferable.

The method for producing such a modified polysiloxane represented by the general formula (I) is not particularly limited. For example, the present inventors have found the method and have already filed a patent application.
It is preferable to synthesize according to the method for synthesizing a long-chain alkyl-modified polysiloxane described in JP-A-8310. That is, the living polyethylene obtained after the polymerization of ethylene is reacted with a cyclic siloxane, and the cyclic siloxane, a linear polysiloxane having a silanol group at the end, or a mixture thereof is polymerized in the presence of a catalyst, so that a long end is obtained at both ends. A polysiloxane having a chain saturated hydrocarbon group can be synthesized with good reproducibility.

The modified polysiloxane having a long-chain saturated hydrocarbon group at both terminals represented by the general formula (I) thus synthesized has a crystalline hydrocarbon group having a high melting point at both terminals. This means that when the temperature is high, sweating, rain,
The hair cosmetics to be blended can be provided with effects such as continuously imparting a good feel even when wet by sports or the like and high humidity, protecting from external stimuli, and improving the fixability of the active ingredient. Further, since it has a long-chain hydrocarbon group only at both terminal portions, it has a feature that a siloxane portion can be contained in a molecule at a high ratio, and gloss and the like peculiar to silicone can be imparted.

The amount of the modified polysiloxane represented by the general formula (I) in the hair cosmetic composition of the present invention is not particularly limited, but is preferably 0.1 to 50% by weight, more preferably 0.1 to 20% by weight. .

The hair cosmetic composition of the present invention essentially imparts a good feel and exhibits a protective effect against external irritation by the modified polysiloxane represented by the general formula (I). It is preferable to include a cationic surfactant as an active ingredient for increasing the water content. As the cationic surfactant, known ones conventionally used in hair cosmetics can be appropriately selected and used, and among them, quaternary ammonium salts are preferably used. A quaternary ammonium salt as described in JP-A-108719, that is, a quaternary ammonium salt represented by the following general formula (II) can be used.

[0021]

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[In the above formula, one or two of R ^{4 to} R ⁷ are a linear or branched alkyl group having 8 to 28 carbon atoms,
Hydroxyalkyl group or the formula R ⁸ of 8 to 28 carbon atoms _{- (CH 2 CH 2 O)} r - (R 8 represents an alkyl or hydroxyalkyl group having a carbon number of 8 to 28 8 to 24 carbon atoms, r is The remainder is a benzyl group, an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group having 1 to 3 carbon atoms, and X ^- is a halogen ion or an organic anion. Is shown. Particularly preferred among the quaternary ammonium salts represented by the general formula (II) are branched quaternary ammonium salts represented by the following general formula (III) or (IV).

[0023]

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[In the above formula, R ⁹ and R ¹⁰ represent the formula (V)

[0025]

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A branched alkyl group represented by the formula (VI) and an alkyl group selected from the linear alkyl groups represented by the formula (VI) CH ₃ (CH ₂ ) _q- (VI) (in the formulas (V) and (VI) , R ¹³ is a methyl group or an ethyl group, p and q are numbers each having a total carbon number of 8 to 16 in the formula (V) or (VI)), and the branching ratio (V) of the groups R ⁹ and R ¹⁰ / (V) + (VI) is 10 to 100% by weight, and R ¹¹ and R ¹² are selected from a benzyl group, an alkyl group having 1 to 3 carbon atoms and a hydroxyalkyl group having 1 to 3 carbon atoms. And X ^- has the same meaning as described above. ]

[0027]

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[In the above formula, R ¹⁴ and R ^{15 each} have 2 carbon atoms.
Represents an alkyl group of ~ 12, and R ¹⁶ is a group represented by the formula

[0029]

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(R ¹⁴ and R ¹⁵ have the same meanings as above) or an alkyl group having 1 to 3 carbon atoms, and R ¹⁷ and R ¹⁸ are a benzyl group and an alkyl group having 1 to 3 carbon atoms. And a group selected from hydroxyalkyl groups having 1 to 3 carbon atoms, and X ^- has the above-mentioned meaning. The amount of such a quaternary ammonium salt in the hair cosmetic composition of the present invention is not particularly limited, but is preferably 0.1 to 20% by weight, more preferably 0.5 to 5% by weight.

In the present invention, oils generally used for hair cosmetics may be blended, for example, higher alcohols having a linear or branched alkyl or alkenyl group, liquid paraffin, petrolatum And animal and plant fats and oils such as hydrocarbons such as solid paraffin, lanolin derivatives, higher fatty acid esters, higher fatty acids, higher fatty acid amides, mink oil and olive oil, and modified polysiloxanes represented by the formula (I) Other silicone oils such as polydimethylsiloxane, cyclic polydimethylsiloxane, polymethylphenylsiloxane and the like can be used. The amount of these oils is usually 0.1 to 30% by weight in the hair cosmetic, preferably
1. Make it 0 to 10% by weight.

Since the modified polysiloxane represented by the general formula (I) allows these surfactants and oils to remain on the skin continuously, it imparts a better feel and a higher protective effect from external stimuli. Obtainable.

The hair cosmetic composition of the present invention further comprises, if necessary, components other than the above-mentioned components, which are usually used in hair cosmetics.
For example, aqueous components, emulsifiers, preservatives, antioxidants, fragrances,
Optional components such as powders, alcohols, natural polymer compounds, and synthetic polymer compounds can be appropriately compounded within a range that does not impair the effects of the present invention, and include liquids, solid dispersions, solids, and pastes (semi-solids). ), Gel, water-in-oil or oil-in-water emulsion, foam and the like.

The hair cosmetic of the present invention can be produced according to a usual method, and includes, for example, a hair rinse, a hair conditioner, a hair treatment, a conditioning shampoo, a hair cream, a styling lotion, a styling mousse, a conditioning mousse,
It can be applied as a hair spray, styling spray, hair dye and the like.

[0035]

EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples.

Example 1 (Hair Rinsing Agent) A hair rinsing agent was prepared by uniformly mixing the components having the composition shown in Table 1, and for each of the obtained hair rinsing agents, a hair conditioning effect (moist feeling, softness) was obtained according to the following method. , Smoothness, oiliness and squeaky feeling in a wet state) were evaluated. Table 1 shows the results.

<Test Method and Evaluation Method for Hair Conditioning Effect> Hair of a Japanese woman with a length of 15 cm (average 80 μm)
m) 20 g were bundled, wound into a lot, and subjected to a perm treatment with a commercially available perm agent. After that, wash with commercial shampoo,
After rinsing with warm water, apply a hair rinse to the entire surface, then rinse with running water for 30 seconds, wipe off the moisture with a towel, and comb the wet hair with a comb with a comb tooth spacing of 2 mm. For the degree, a sensory evaluation (a 4-level evaluation) was performed by 10 expert panelists, and the rank closest to the average was taken as the evaluation result. Next, the hair whose moisture was wiped off with a towel was dried with a drier, and a tenth panel of experts evaluated the moistness, flexibility, smoothness, and oiliness (4-grade evaluation). Closer ranks were used as the evaluation results.

(A) Evaluation criteria of "moist feeling" Rank condition A Very moist B Moist C slightly moist D Not moist (b) Evaluation criteria of "flexibility" Rank condition A Very soft Case B Soft case C Slightly hard D Hard case (c) Evaluation criteria of "smoothness" Rank State A Very smooth case B Smooth case C Slightly non-smooth D Not smooth (d) Evaluation criteria Rank status A No oiliness B Oiliness somewhat C Oiliness D Very oiliness (e) Evaluation criteria for "wetness squeakiness" Rank condition A Kizziness When there is no B When there is a slight squeaky feeling C When there is a squeaky feeling D When there is a considerable squeaky feeling.

[0039]

[Table 1]

Note) * 1: In the general formula (I), R ¹ = R ² = CH ₃ , R ³ = C ₇₀ H
₁₄₁ (average carbon number), n = 400 (average value) * 2: In the general formula (I), R ¹ = CH ₃ , R ² = C ₆ H ₅ (phenyl group), R ³ = C ₄₀ H ₈₁ ( (Average carbon number), n = 100 (average value) * 3: SM-8702C manufactured by Dow Corning Toray Silicone Co., Ltd. * 4: KF-96-1000cs (viscosity 1000cs) manufactured by Shin-Etsu Chemical Co., Ltd. The hair rinsing agent of the present invention imparts a moist feeling and flexibility to the hair, has no oily feeling or sticky feeling, and does not cause a squeaky feeling when applied to wet hair. showed that. In addition, a good smooth feeling could be imparted to the hair, and the hair could be prevented from becoming loose. In addition, bulkiness of the scalp could be suppressed. on the other hand,
The hair rinse agent of the comparative product was inferior to the product of the present invention in the evaluation items of the above hair conditioning effect test.

Example 2 (Hair treatment agent) A hair treatment agent having the following composition was prepared by uniformly mixing the following components. The obtained hair treatment agent was excellent in moist feeling, flexibility, and smoothness, without oily feeling and squeaky feeling in a wet state, and gave a good feeling.

Component content (% by weight) 両 C _{50 at} both ends Modified dimethylpolysiloxane ^{* 1} 3.0 2-Dodecylhexadecyltrimethylammonium chloride 1.0 Stearyltrimethylammonium chloride 1.5 Cetanol 4.0 Diethylene glycol ethyl ether 5.0 Glycerin 5.0 Isopropyl palmitate 1.0 Hydroxyethylcellulose 0.3 Citric acid 0.05 Perfume 0.3 Water balance ─── 100 Total 100 Note) * 1: In general formula (I), R ¹ = R ^{_{2 = CH 3, R 3 =}} C 50 H 101 ( average carbon number), n = 400 (average value) example 3 (hair rinse) by mixing the following ingredients uniformly, to prepare a hair rinse of the following composition The obtained hair rinsing agent was excellent in moist feeling, flexibility and smoothness, had no oily feeling and no squeaky feeling in a wet state, and gave a good feel.

Component content (% by weight) 両 C _{45 at} both ends Modified methylphenylpolysiloxane ^{* 1} 2.0 Amino-modified silicone ^{* 2} 1.0 Propylene glycol 3.0 Glycerin 2.0 Stearyltrimethylammonium chloride 1.0 Stearyl alcohol 3.0 Isotridecyl myristate 0.2 Methylparaben 0.1 Hydroxycellulose aqueous solution ^{* 3} 0.4 Fragrance 0.4 Water balance ───────計 Total 100 Note) * 1: In general formula (I), R ¹ = CH ₃ , R ² = C ₆ H ₅ (phenyl group), R ³ = C ₄₅ H ₉₁ (average carbon number), n = 100 (average value) * 2: SM8702 manufactured by Dow Corning Toray Silicone Co., Ltd. * 3: 1% aqueous solution / viscosity 8000cp Example 4 (Hair treatment agent) By uniformly mixing the above components, a hair treatment agent having the following composition was prepared. The obtained hair treatment agent was excellent in moist feeling, flexibility, and smoothness, without oily feeling and squeaky feeling in a wet state, and gave a good feeling.

Component Content (% by weight) ％ C ₁ -C ₄₅ Modified dimethylpolysiloxane ^{* 1} 3.0 Dimethylpolysiloxane (degree of polymerization 3000) 1.5 Dimethylpolysiloxane (degree of polymerization 300) 5.0 Diethylene glycol ethyl ether 5.0 Stearyltrimethylammonium chloride 2.0 Dialkyldimethylammonium chloride ^{* 2} 1.0 Cetanol 4.0 Palmitic acid Isopropyl 1.0 Polyoxyethylene stearyl ether (SEO) 0.5 Methyl paraben 0.2 Fragrance 0.5 Water Balance ───────────────────────────────── 100 Total 100 Note) * 1: In formula (I), R ¹ = R ² = CH ₃ , R ³ = C ₄₅ H ₉₁ (Average carbon number, provided that the number of carbon atoms is 3rd from the terminal methyl group. Minute of methyl group Yes), n = 200 (average value) * 2: Branched quaternary ammonium salt derived from a commercially available oxo synthetic alcohol having 12 to 15 carbon atoms (manufactured by Mitsubishi Yuka Co., Ltd.) (branching ratio: 20%) Example 5 ( Conditioning mousse) A conditioning mousse having the following composition was prepared from the following components by a conventional method. The obtained conditioning mousse was excellent in moist feeling, flexibility and smoothness, without oily feeling and squeaky feeling in a wet state, and gave good feeling.

Component Content (% by weight) 両 C _{40 at} both ends Modified dimethylpolysiloxane ^{* 1} 1.0 Dimethylpolysiloxane (degree of polymerization 120) 1.5 Glycerin 2.5 Isopropyl palmitate 2.5 2-hexyldecyltrimethylammonium chloride 0.5 Polyoxyethylene sorbitan monostearate 0.2 95% ethanol 5.0 Methylparaben 0.1 Perfume 0.1 LPG ^{* 2} 10.0 Water balance ─────────────────────────────────── Total 100.0 Note) * 1: In general formula (I) , R ¹ = R ² = CH ₃ , R ³ = C ₄₀ H ₈₁ (average carbon number), n = 100 (average value) * 2: 4.0 kg / cm ² , 20 ° C. Example 6 (hair dye) A hair dye having the following composition was prepared by the conventional method. The obtained hair dye had excellent moistness, flexibility and smoothness, no oily feeling, no squeaky feeling in a wet state, and gave a good feel.

Component Content (% by weight) 両 C _{40 at} both ends Modified dimethylpolysiloxane ^{* 1} 0.5 Ethanol 20.0 Benzyl alcohol 3.0 Brown 201 0.6 Yellow 4 0.6 Black 401 0.2 Xanthan gum 2.0 Preservative 0.1 Perfume 0.02 Water balance ───────────────── ────────────────── Total 100.0 Note) * 1: In general formula (I), R ¹ = R ² = CH ₃ , R ³ = C ₄₀ H ₈₁ (average (Carbon number), n = 100 (average value) Example 7 (conditioning shampoo) The following components were blended by a conventional method to prepare a conditioning shampoo having the following composition. The obtained conditioning shampoo was excellent in moist feeling, flexibility and smoothness, without oiliness and without squeaky feeling in a wet state, and gave a good feel.

Component Blended amount (% by weight) ─────────────────────────────────── C _{40 at} both ends Modified dimethylpolysiloxane ^{* 1} 0.5 Polyoxyethylene (3.0) lauryl ether triethanolamine sulfate 8.0 lauroyl-N-methyl-β-alanine sodium salt ^{* 2} 8.0 lauric acid diethanolamide ^{* 3} 5.0 cationized cellulose ^{* 4} 0.5 preservative 0.1 Dye, fragrance, pH adjuster Appropriate amount Water balance ─────────────────────────────────── Total 100.0 Note) * 1: In the general formula (I), R ¹ = R ² = CH ₃ , R ³ = C ₄₀ H ₈₁ (average carbon number), n = 100 (average value) * 2: Alanon AIE manufactured by Kawaken Fine Chemical Co. * 3: Kawaken Fine Chemical's Amizole CDE * 4: Union Carbide's polymer JR-400 Example 8 Tiling spray) The following components were blended in a conventional manner to prepare a styling spray having the following composition. The obtained styling spray was excellent in moistness, flexibility and smoothness, without oiliness and squeaky feeling in a wet state, and gave a good feel.

Component Content (% by weight) 両 C _{40 at} both ends Modified dimethylpolysiloxane ^{* 1} 0.5 Methacrylate polymer 2.5 LPG (propellant) 50.0 Fragrance 0.1 Ethanol Balance ─────────────────────────── ──────── Total 100.0 Note) * 1: In the general formula (I), R ¹ = R ² = CH ₃ , R ³ = C ₄₀ H ₈₁ (average carbon number), n = 100 (average value) )

Claims (4)

[Claims] 1. A hair cosmetic comprising a modified polysiloxane represented by the general formula (I). Embedded image [Wherein, R ¹ and R ² may be the same or different, and each may be an alkyl group having 1 to 6 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted with an alkyl group. Is shown. However,
The (n + 2) R ¹ groups and the (n + 2) R ² groups may be the same or different. R ³ represents a linear or branched saturated hydrocarbon group having an average carbon number of 16 to 600. However, the two R ³ groups may be the same or different. n: The average value shows the number of 0-3000. ] 2. The hair cosmetic according to claim 1, wherein in formula (I), the R ³ group is a linear or branched saturated hydrocarbon group having an average of 40 to 300 carbon atoms. 3. In the general formula (I), the average value of n is 1
The hair cosmetic according to claim 1, wherein the amount is from 00 to 3,000. 4. In the general formula (I), 2 represented by R ³
The hair cosmetic according to any one of claims 1 to 3, wherein the weight ratio of the sum of the two saturated hydrocarbon group parts to the remaining polysiloxane part is 30:70 to 1:99.