JPH10310509A - Hair cosmetic - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a hair cosmetic excellent in conditioning activities and usability, and hardly imparting a sticky feeling to the hair by including a specific silicone compound modified with a fluorinated alkyl in combination with a (poly)glycerin. SOLUTION: This hair cosmetic is obtained by formulating 0.001-80 wt.% silicone compound modified with a fluorinated alkyl in combination with a (poly)glycerin, of formula I R<1> to R<12> is each a 1-10C alkyl or a phenyl with the proviso that one or more of the R<1> to R<12> is a fluorine-substituted alkyl, and further another one or more thereof is formulas II to IV [Q is a 1-10C divalent hydrocarbon; (1) is 1-20; (m) is 1-20]; (p), (q) and (r) are each 10, and when (p)=(q)=0 and (r)≠0, one or more of R<1> to R<3> and R<8> to R<12> are each a fluorine-substituted alkyl and formulas II to TV, and when (p)=(r)=0 and (q)≠0, one or more of R<1> to R<3> , R<6> to R<7> and R<10> to R<12> are each a fluorine- substituted alkyl and formulas II to IV, and when (p)≠0 and (q)=(r)=0, one or more of R<1> to R<5> and R<10> to R<12> are each a fluorine-substituted alkyl and formulas II to IV, etc.} based on the hair cosmetic.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a fluorine-containing alkyl (poly) having a fluorine compound-containing group and a hydrophilic group simultaneously.
By blending a glycerin co-modified silicone compound, it has excellent conditioning effect and usability, and
The present invention relates to a hair cosmetic which is non-greasy, glossy, and excellent in setting power.

More specifically, when a fluorine-alkyl / (poly) glycerin co-modified silicone compound is used as a conditioning agent, a shampoo, rinse and conditioner excellent in conditioning effect and usability can be obtained. The present invention relates to a hair styling agent which is non-greasy, glossy, has excellent setting power, and has a long lasting setting effect.

[0003]

2. Description of the Related Art Detergents such as shampoos in hair care products not only have basic functions as detergents such as detergency and foaming property, but also have good foam quality and finger passing during and during hair washing. The important points are that the hair has good usability, for example, the hair does not squeak, and that the hair has a good finished feeling, such as ease of uniting, suppleness, and good combability after drying. Therefore, there has been proposed a composition in which various oils such as a cationic polymer, an ester oil, and a silicone oil are blended in a detergent base.

[0004]

However, in the case where a conventional cationic polymer or silicone oil is blended, a sufficient conditioning effect cannot be obtained. Furthermore, in recent years, for the purpose of improving these effects, blending of an alkyl polyalkylene glycol ether, a silicone derivative, a perfluoropolyether, or the like has been attempted. Due to poor compatibility, there was a problem that satisfactory feeling of use and finish could not be obtained.

On the other hand, oils such as silicone oil and cationic surfactants are used as hair styling agents for the purpose of giving the hair suppleness and luster. Particularly, silicone oil has been widely used in recent years because of its low surface tension, excellent lubricity of hair, and luster. However, when the silicone oil is used in a large amount or used for a long time, there is a drawback that the hair has a squeaky feeling. Therefore, it has excellent conditioning effect and usability, and it is not sticky to hair,
There has been a demand for the development of a conditioning agent and a setting agent having a good luster and excellent setting power.

[0006]

In view of the above circumstances, as a result of intensive studies, when a fluorine-alkyl / (poly) glycerin co-modified silicone compound is used as a conditioning agent, a shampoo and a rinse excellent in conditioning effect and usability are provided. , A conditioner is obtained, and
When used as a setting agent, the present inventors have found that a hair styling agent which is non-greasy, has good gloss, is excellent in setting power, and has a good sticky property can be obtained, and has completed the present invention.

That is, the present invention provides a conditioning effect and usability by blending a fluorine-alkyl / (poly) glycerin co-modified silicone compound represented by the following general formula (1). The present invention relates to a hair cosmetic which is non-greasy, has a good luster, and is excellent in setting power.

[0008]

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[Wherein, R ^{1 to} R ¹² may be the same or different and represent an alkyl group having 1 to 10 carbon atoms or a phenyl group, at least one of which is a fluorine-substituted alkyl group; At least one of the following formula (A):
(B) or (C)

[0010]

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[0011]

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[0012]

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(Wherein Q is a divalent hydrocarbon group having 1 to 10 carbon atoms, l is a positive integer of 1 to 20 and m is a positive integer of 1 to 20), and p, q and r are Each is an integer of 0 or more, but when p = q = 0 and r ≠ 0, R ^{1 to} R ³ and R ⁸
At least one of R 1 to R ¹² represents a fluorine-substituted alkyl group or a group represented by the above formula (A), (B) or (C), and when p = r = 0 and q ≠ 0, R ^{1 to} R ³ , R ⁶ -R ⁷ , R
^At least one of ^{10 to} R ¹² represents a fluorine-substituted alkyl group and a group represented by the above formula (A), (B) or (C), and when p ≠ 0 and q = r = 0, R ^{1 to} R 12 ⁵ , at least one of R ^{10 to} R ¹² represents a fluorine-substituted alkyl group and a group represented by the above formula (A), (B) or (C), and p =
0, when q = r ≠ 0, at least one of R ^{1 to} R ³ and R ^{6 to} R ¹⁵ is a fluorine-substituted alkyl group, and the above formula (A);
A group represented by (B) or (C), p = r ≠ 0,
When q = 0, at least one of R ^{1 to} R ⁵ and R ^{8 to} R ¹² represents a fluorine-substituted alkyl group and a group represented by the above formula (A), (B) or (C), and p = q When ≠ 0 and r = 0, at least one of R ^{1 to} R ⁷ and R ^{10 to} R ¹² represents a fluorine-substituted alkyl group and a group represented by the above formula (A), (B) or (C); When p = q = r = 0, R ^{1 to} R ³ , R
At least one fluorine-substituted alkyl group having ¹⁰ to R ^12, and the above formula (A), a group represented by (B) or (C). Hereinafter, the present invention will be described in detail.

The fluorine-alkyl / (poly) glycerin co-modified silicone compound used in the present invention is a compound in which monoglycerin and / or polyglycerin are bonded to a silicone chain via a spacer as shown in the above general formula (1). . In the compound represented by the general formula (1), R ^{1 to} R ¹² may be the same or different, and have 1 carbon atom.
Represents an alkyl group or a phenyl group, for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group,
Hexyl group, heptyl group, octyl group, nonyl group, dekel group, cyclopentyl group, cyclohexyl group, phenyl group, tolyl group, and the like, and at least one of R ^{1 to} R ¹² is a fluorine-substituted alkyl group, For example, trifluoropropyl group, nonafluorohexyl group, heptadecafluorodecyl group and the like, or even R ¹ ~
At least one of R ^{12 is} a group represented by the above formula (A), (B) or (C), and examples thereof include monoglycerin, diglycerin, triglycerin, and tetraglycerin.

When the fluorine-alkyl / (poly) glycerin co-modified silicone compound of the present invention is blended into a hair cosmetic, it varies depending on the dosage form.
0.001 to 80% by weight (hereinafter simply referred to as “%”),
In particular, it is preferable to mix 0.1 to 40%.

In the present invention, hair cosmetics include shampoos, hair rinses, rinse-in shampoos, hair treatments, hair conditioners, hair styling agents, and the like.
Includes all hair products topically applied to hair, including topical medicines.

In the hair cosmetic composition of the present invention, in addition to the above-mentioned components, cationic surfactants, nonionic surfactants and anionic surfactants used in ordinary hair cosmetics as long as the effects of the present invention are not impaired. Activator, activator such as amphoteric surfactant, solid, semi-solid, liquid oil, water, water-soluble polymer, polyhydric alcohol, higher alcohol, powder, resin, organically modified clay mineral, polymer compound, ultraviolet light Absorbent, humectant, preservative, bactericide, fragrance, antioxidant, sequestering agent, p
An H preparation agent, a pigment, a component for beautiful skin, a physiologically active component, a solvent, a propellant, and the like can be added.

[0018]

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

Production Example 1 Glycerin monoallyl ether 38.4 of the following formula was placed in a glass flask equipped with a stirrer, thermometer and reflux condenser.
g,

[0020]

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And 200 g of a SiH group-containing fluorine-alkyl-modified silicone represented by the following formula:

[0022]

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100 g of isopropyl alcohol, 0.3 g of a 10% ethanol solution of potassium acetate and 0.3 g of an isopropyl alcohol solution of chloroplatinic acid (2% platinum concentration)
g was heated and reacted at the reflux temperature of isopropyl alcohol for 5 hours. After completion of the reaction, isopropyl alcohol was distilled off under reduced pressure to obtain 211.4 g of a fluoroalkyl / glycerin co-modified silicone represented by the following formula.

[0024]

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Production Example 2 81.4 g of triglycerin monoallyl ether of the following formula was obtained by converting the glycerin monoallyl ether of Production Example 1 to:

[0026]

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The same procedure was repeated except that the above procedure was repeated to obtain a fluorine-alkyl / polyglycerin co-modified silicone represented by the following formula.

[0028]

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Production Example 3 81.4 g of triglycerin monoallyl ether of the following formula was prepared by converting the glycerin monoallyl ether of Production Example 1 to:

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The same procedure was repeated except that the above procedure was repeated, to obtain 246.6 g of a fluorine-alkyl / polyglycerin co-modified silicone represented by the following formula.

[0031]

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Production Example 4 196.3 g of the SiH group-containing fluorine-alkyl-modified silicone represented by the following formula was prepared from the SiH group-containing fluorine-alkyl-modified silicone of Production Example 1.

[0033]

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The same operation as in Production Example 3 was carried out, except that 243 g of a fluorine-alkyl / polyglycerin co-modified silicone represented by the following formula was obtained.

[0035]

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Production Example 5 142.3 g of the SiH group-containing fluoroalkyl-modified silicone represented by the following formula was prepared by converting the SiH group-containing fluoroalkyl-modified silicone of Production Example 1 to the following formula.

[0037]

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The same procedure as in Production Example 3 was carried out, except that the substitution was made, to obtain 194.7 g of a fluorine-alkyl / polyglycerin co-modified silicone represented by the following formula.

[0039]

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Examples 1 to 4 and Comparative Examples 1 to 4 Shampoos Shampoos having the respective compositions shown in the following Table 1 were produced, and their usability was evaluated.

[0041]

[Table 1]

(Production Method) A: Components 1 to 6 were mixed by stirring to obtain a product.

(Evaluation) A use test was conducted by a panel of 50 women, and the foaming property, detergency, feeling of use during hair washing, and feeling of finish were evaluated according to the following criteria, and the average score was determined. [Evaluation criteria] 5 points: Very good 4 points: Good 3 points: Normal 2 points: Somewhat poor 1 point: Poor [Judgment] ：: Average score of 4.5 or more ○: Average score of 3.5 or more and less than 4.5 Δ: Average score of 2.5 or more and less than 3.5 ×: Average score of less than 2.5 The obtained results are shown in Table 2.

[0044]

[Table 2]

As is clear from the results in Table 2, the shampoos of Examples 1 to 4 containing the fluorine-alkyl / (poly) glycerin co-modified silicone compound of the present invention were compared with Comparative Example 1.
Compared to No. 4, the foaming property and the washing property were excellent, and the finger feeling was good and the hair was not squeezed.

Examples 5 to 6 and Comparative Examples 5 to 6 Hair conditioners Hair conditioners having the compositions shown in Table 3 below were produced, and their usability was evaluated.

[0047]

[Table 3]

(Production Method) A: Components 1 to 4 were stirred and mixed to obtain a product.

(Evaluation) A use test was conducted using a panel of 50 women, and evaluation was performed on the above-described criteria for spread during application, finger passage during application, finger passage during rinsing, gloss during drying, and finished feeling. The judgment was made based on the average score. Table 4 shows the results.

[0050]

[Table 4]

As is evident from the results in Table 4, the hair conditioners of Examples 5 and 6 containing the fluorine-alkyl / (poly) glycerin co-modified silicone compound of the present invention had a lower effect on application than Comparative Examples 5 and 6. It had good spreadability and finger passage, and good finger passage during rinsing, and very good gloss and finish when dry.

Example 7 Styling mousse A styling mousse having the following composition was produced and its usability was evaluated.

(Composition) (%) 1. Polyvinylpyrrolidone / vinyl acetate copolymer 5.0 2. Fluoroalkyl / (poly) glycerin co-modified 1.0 Silicone compound (Production Example 3) Ethanol 10.0 4. Preservative qs. Appropriate amount of fragrance 6. Remaining purified water 7. Propellant 3.0

(Production method) A: Components 1 to 6 are uniformly mixed. B: A and Component 7 were filled in an aerosol can to obtain a styling mousse. The styling mousse of Example 7 was non-greasy, glossy, and excellent in setability, and very easy to use.

[0055]

As described in detail above, the fluorine alkyl
Hair cosmetics containing a (poly) glycerin co-modified silicone compound have excellent conditioning effect and usability, and are non-sticky, glossy, have excellent setting power, and have a long lasting set effect. Is good.

Claims (1)

[Claims] 1. A hair cosmetic comprising a fluorine-alkyl / (poly) glycerin co-modified silicone compound represented by the following general formula (1). Embedded image [Wherein, R ^{1 to} R ¹² may be the same or different and represent an alkyl group having 1 to 10 carbon atoms or a phenyl group;
At least one is a fluorine-substituted alkyl group, and further, at least one is of the following formula (A), (B) or (C): Embedded image Embedded image (However, Q is a divalent hydrocarbon group having 1 to 10 carbon atoms, l is 1
-20 and m are positive integers of 1-20. ), P, q, and r are each an integer of 0 or more.
When q = 0 and r ≠ 0, at least one of R ^{1 to} R ³ and R ^{8 to} R ¹² is a fluorine-substituted alkyl group, and the above formula (A)
A group represented by (B) or (C), p = r = 0,
When q ≠ 0, at least one of R ^{1 to} R ³ , R ^{6 to} R ⁷ , and R ^{10 to} R ¹² is a fluorine-substituted alkyl group, and the above formula (A);
A group represented by (B) or (C), p ≠ 0, q =
When r = 0, at least one of R ^{1 to} R ⁵ and R ^{10 to} R ¹² represents a fluorine-substituted alkyl group and a group represented by the above formula (A), (B) or (C), and p = 0 , Q = r ≠ 0, at least one of R ^{1 to} R ³ and R ^{6 to} R ¹⁵ represents a fluorine-substituted alkyl group and a group represented by the above formula (A), (B) or (C) , P = r ≠ 0, q ¹ = 0
At least one of R ⁵ and R ^{8 to} R ¹² represents a fluorine-substituted alkyl group or a group represented by the above formula (A), (B) or (C), and when p = q ≠ 0 and r = 0 R ^{1 to} R ⁷ , R ¹⁰ to
At least one of R ¹² represents a fluorine-substituted alkyl group and a group represented by the above formula (A), (B) or (C);
When p = q = r = 0, at least one of R ^{1 to} R ³ and R ^{10 to} R ¹² is a fluorine-substituted alkyl group, and the above formula (A)
It represents a group represented by (B) or (C). ]