JPH10310506A - Low irritant cosmetic - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject cosmetic hardly causing skin irritation and having skin-protecting activities by including a silicone compound modified a specific fluoroalkyl in combination with a (poly)glycerin. SOLUTION: This low irritant cosmetic is obtained by formulating 0.1-30 wt.% silicone compound modified with a fluoroalkyl in combination with a (poly)glycerin, of formula I R<1> to R<12> are each a 1-10C alkyl or phenyl, and one or more thereof are fluorine-substituted alkyls, and another one or more are formulas II to TV [Q is a 1-10C divalent hydrocarbon; (1) is 1-20; (m) is 1-20]; (p), (q) and (r) are each 0 or more, and when (p)=(q)=0 and (r)≠0, one or more of R<1> to R<3> , and R<8> to R<12> are the fluorine-substituted alkyl, and formulas If to IV, 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 the fluorine-substituted alkyl or formulas II to TV, 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 the fluorine-substituted alkyl or formulas II to IV, etc.}.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION An object of the present invention is to provide a highly safe cosmetic containing a silicone compound having a specific structure.

[0002] More specifically, a hypoallergenic cosmetic having a low skin irritation and a protective effect on the skin, containing a fluorine alkyl / (poly) glycerin co-modified silicone compound having both a fluorine compound-containing group and a hydrophilic group. It is about.

[0003]

2. Description of the Related Art Hitherto, a polyether-modified silicone having a polyoxyalkylene group has been used as a nonionic surfactant. In addition, it is known that polyether-modified silicone has an effect of relieving irritation when shampoo gets into eyes by relieving irritation of other irritants or blending in shampoo.

[0004]

The polyether-modified silicone, however, has less skin irritation than surfactants such as sodium lauryl sulfate, but has not been sufficient. Therefore, there has been a demand for the development of a material having an effect of alleviating skin irritation and having less skin irritation of the compound itself, and a cosmetic containing the same.

[0005]

Means for Solving the Problems In view of the above-mentioned circumstances, as a result of intensive studies, it has been found that when a fluorine-alkyl / (poly) glycerin co-modified silicone compound is used in cosmetics, skin irritation is reduced and the skin has a protective effect. And completed the present invention.

[0006] That is, the present invention provides a skin protective property by blending a fluorine-alkyl / (poly) glycerin co-modified silicone compound represented by the following general formula (1).
The present invention relates to a cosmetic having excellent hypoallergenicity.

[0007]

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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)

[0009]

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[0010]

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[0011]

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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 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. Also, a wide range of HLB compounds is possible depending on the number of p, q, and r.

When the fluorine-alkyl / (poly) glycerin co-modified silicone compound of the present invention is incorporated into a cosmetic,
It is preferable to add 0.1 to 30% by weight (hereinafter simply referred to as "%").

The cosmetics in the present invention include not only make-up cosmetics, skin cosmetics and hair cosmetics used as oils, emulsifiers and detergents but also all products used externally on the skin, such as external medicines. .

In the cosmetic of the present invention, in addition to the above components,
Solid, semi-solid, liquid oils, water, water-soluble polymers, polyhydric alcohols, solvents, surfactants, powders, resins, organically modified solid cosmetics used in ordinary cosmetics as long as the effects of the present invention are not impaired. A clay mineral, a polymer, an ultraviolet absorber, a humectant, a preservative, a bactericide, a fragrance, an antioxidant, a beautiful skin component, a physiologically active component, and the like can be added.

[0017]

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,

[0019]

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

[0021]

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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 (platinum concentration: 2%)
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.

[0023]

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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:

[0025]

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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.

[0027]

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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.

[0030]

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

[0032]

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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.

[0034]

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Production Example 5 142.3 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.

[0036]

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

[0038]

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

[0040]

[Table 1]

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

(Evaluation) A use test was conducted by a panel of 50 women, and the foaming property, washability, hand roughness, use feeling during hair washing, and finish feeling were evaluated according to the following criteria.
The judgment was made based on the average score. [Evaluation Criteria] 5 points: Very good 4 points: Good 3 points: Normal 2 points: Slightly poor 1 point: Bad 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.

[0043]

[Table 2]

As is evident from the results in Table 2, the shampoo of Example 1 containing the fluorine-alkyl / (poly) glycerin co-modified silicone compound of the present invention is superior in foaming property and detergency as compared with Comparative Example 1. The usability and finish during hair washing were good, and the usability and safety were excellent, as the hands were not rough.

Example 2 and Comparative Example 2 Hand Lotion Hand lotions having the compositions shown in Table 3 below were produced, and their usability was evaluated.

[0046]

[Table 3]

(Production method) A: Components 1 to 3 are mixed. B: Component 4 is heated. C: Add A to B and dissolve to obtain a hand lotion.

(Evaluation) A test for safety and a test for skin protective effect were performed. In the safety test, a skin cumulative irritation test and a human patch test were performed and evaluated by the following methods.

Cumulative skin irritation test Three rabbits were applied once a day, five times in total. Each time, erythema, edema and eschar were visually observed, and when no reaction occurred, “no irritation” was evaluated, and when a reaction occurred, “irritation” was evaluated.

A human patch test panel was obstructed and adhered to the upper arm flexion side of 20 panelists. Twenty-four hours later, erythema, edema, and eschar were visually observed and evaluated by the number of people who had a reaction.

Skin protection effect test A use test was conducted by a panel of 10 women, a hand lotion was applied to the hands, washed with water, inspected for the roughness of the skin surface, and evaluated according to the following criteria. Was determined. [Evaluation Criteria] 5 points: Not rough and moist. 4 points: Not rough at all. 3 points: Normal. 2 points: Rough and rough. 1 point: Hand rough. [Determination] ：: 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 Table 4 shows the obtained results. Shown in

[0052]

[Table 4]

As is evident from the results in Table 4, the hand lotion of Example 2 in which the fluorine-alkyl / (poly) glycerin co-modified silicone compound of the present invention was blended had a very excellent skin protection effect as compared with Comparative Example 2. Was what it was.

Example 3 Sun-cutting agent A sun-cutting agent having the following composition was produced and its usability was evaluated.

(Composition) (%) 1. Fluoroalkyl / (poly) glycerin co-modified 10.0 Silicone compound (Production Example 1) Sodium cetyl sulfate 1.03. 3. Octamethylcyclotetrasiloxane 63.0 Octyl paramethoxycinnamate 6.0 5. Ethanol 10.0 6. Preservative appropriate amount 7. Appropriate amount of flavor 8. Purified water balance

(Manufacturing method) A: Components 1 to 8 are mixed to obtain a suncut agent. Example 3 was a very good suncut agent which had a high sunscreen effect and had little skin irritation and no rough skin.

[0057]

As described in detail above, the fluorine alkyl
Cosmetics containing a (poly) glycerin co-modified silicone compound are excellent in skin protection and low irritation.

Claims (1)

[Claims] 1. A hypoallergenic 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). ]