JPH09194335A - Hair cosmetics - Google Patents

Abstract

(57) [Abstract] [PROBLEMS] To provide a hair cosmetic composition having good product stability and capable of imparting gloss, suppleness, slipperiness, and moisturizing feeling to hair. A hair cosmetic containing an organopolysiloxane represented by the following chemical formula 1. Embedded image However, R in the formula is a monovalent hydrocarbon group having 1 to 20 carbon atoms, A is _a monovalent group represented by -R ^1- (NR ² -R ³ ) _a -NR ⁴ R ⁵ , and X is
Is a monovalent group represented by R, A or —OR ⁷ , and m is 5 to 500
, N is a positive number from 0 to 100, and when n = 0, at least one X is A. However, R in the above formula
¹ is a divalent hydrocarbon having 1 to 8 carbon atoms, R ² , R ⁴ and R ⁵
Is a hydrogen atom directly linked to a nitrogen atom or -CH ₂ CH (OH) CH
_A monovalent group represented by ₂ (OC ₂ H ₄ ) _b (OC ₃ H ₆ ) _c OR ⁶ , R ² ,
The total amount of R ⁴ and R ⁵ is 30 mol% of the total NH in such a group.
And above, R ³ is a divalent hydrocarbon group having 1 to 4 carbon atoms, a
Is an integer of 0 to 4, R ⁶ is a hydrogen atom or a monovalent hydrocarbon group having 1 to 8 carbon atoms, a monovalent group selected from an acyl group, b
Is an integer of 2 to 20, c is an integer of 1 to 10, and R ⁷ is a hydrogen atom or a monovalent hydrocarbon group having 1 to 8 carbon atoms. Embedded image Embedded image

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a hair cosmetic,
In particular, it relates to a hair cosmetic containing a special organopolysiloxane having excellent dispersibility in water as an essential component.

[0002]

2. Description of the Related Art Hair is prone to mechanical damage due to brushing, washing, etc., and physical or chemical damage due to sun rays, dryers, permanent waves, etc., to protect the hair from such damage. To
Conventionally, vegetable oils such as camellia oil and olive oil, animal oils such as lanolin and beef tallow, mineral oils such as petrolatum and paraffin, synthetic oils and the like are directly or dissolved in an emulsion or a solvent to prepare a hair styling agent.

In recent years, it has been found that organopolysiloxane imparts gloss, suppleness, slipperiness and moisturizing feeling to hair, and various hair cosmetics containing it have been put to practical use. There is. For example, a hair cosmetic composition comprising dimethylpolysiloxane and a diol derivative or a branched aliphatic alcohol (JP-A-52-47923).
JP), a hair conditioner composition comprising a polyorganosiloxane-polyoxyalkylene block copolymer and water-containing ethanol or anhydrous ethanol (JP-A-5-58200).
No. 5-136214) and the like are already known.

However, the one containing dimethylpolysiloxane has a drawback that static electricity is easily generated and dust is easily attached. Further, when dimethylpolysiloxane is blended with an aqueous hair cosmetic such as shampoo, hair conditioner, hair rinse, the product stability may be impaired. Further, in the case of blending the polyorganosiloxane-polyoxyalkylene block copolymer, there is a drawback that the effect of imparting slipperiness to hair is not sufficient.

On the other hand, a hair cosmetic composition comprising (aminoalkyl) methylpolysiloxane, a cationic surfactant and an aqueous carrier (JP-A-56-45406), No. 4
Cosmetics using a cationic nitrogen-containing organopolysiloxane (JP-A-55-66506), hair cosmetics using an organopolysiloxane containing an amino group and a polyoxyalkylene group (Japanese Patent Publication No. 6-96499). Cationic hair cosmetics such as Japanese Patent Laid-Open Publications) have also been developed. However, these cosmetics have only been found to have some effect, and have not been satisfactory yet.

[0006]

Therefore, as a result of intensive studies for developing a superior hair cosmetic composition, the present inventors have found that a reaction between a specific organopolysiloxane and a specific polyoxyalkylene glycidyl ether. The present inventors have found that the organopolysiloxane obtained by the method is excellent in the adsorptivity to hair, and at the same time, it is rich in hydrophilicity and the stability when it is used as an aqueous cosmetic composition is improved. Therefore, an object of the present invention is to provide a hair cosmetic composition which can give the hair gloss, suppleness, slipperiness, moisturizing feeling, and the like, and which is excellent in product stability.

[0007]

SUMMARY OF THE INVENTION The above objects of the present invention are as follows.
This is achieved by a hair cosmetic composition containing an organopolysiloxane represented by the following chemical formula 4.

Embedded image However, in the formula, R is a monovalent hydrocarbon group having 1 to 20 carbon atoms, A is a monovalent group represented by the following formula (1), and X is R or A.
Alternatively, a monovalent group represented by the following formula (3), m is 5 to 500
, N is a positive number from 0 to 100, and when n = 0, X
At least one is A.

(1) -R ^1- (NR ² -R ³ ) _a -NR ⁴ R ^{5 wherein} R ¹ is a divalent hydrocarbon group having 1 to 8 carbon atoms, R ² and R ⁴ And R ⁵ is a hydrogen atom directly connected to a nitrogen atom or a monovalent group represented by the following formula (2), wherein the group represented by the formula (2) is the total amount of R ² , R ⁴ and R ⁵ . Of 3
It is 0 mol% or more, R ³ is a divalent hydrocarbon group having 1 to 4 carbon atoms, and a is an integer of 0 to 4. If a exceeds 4, synthesis becomes difficult.

(2) -CH ₂ CH (OH) CH ₂ (OC ₂ H ₄ ) _b (OC ₃ H ₆ ) _c OR ⁶ where R ⁶ is a hydrogen atom or 1 having 1 to 8 carbon atoms. A monovalent group selected from a valent hydrocarbon group and an acyl group, b is an integer of 2 to 20 and c is an integer of 0 to 10; (3) -OR ⁷ provided that R in the formula ⁷ is a hydrogen atom or a monovalent hydrocarbon group having 1 to 8 carbon atoms.

Specific examples of R in the above chemical formula 4 are methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group, tetradecyl group, octadecyl group. Alkyl group such as; vinyl group, alkenyl group such as allyl group; cycloalkyl group such as cyclopentyl group, cyclohexyl group; and aryl group such as phenyl group, tolyl group, naphthyl group, or a carbon atom of these groups And a group in which the hydrogen atom is partially substituted with a halogen atom.

In the present invention, R is particularly preferably a methyl group. Further, as a specific example of the monovalent hydrocarbon group R ^{7 in} the case where X is —OR ⁷ , a methyl group,
Examples thereof include ethyl group, propyl group, pentyl group, hexyl group, octyl group and phenyl group.

M in the chemical formula 4 is a positive number of 5 to 500, and particularly preferably a positive number of 10 to 100. When m is less than 5, the effect of imparting luster and slipperiness to the hair is poor, and when it is more than 500, the stability of the product when incorporated into an aqueous hair treatment agent is reduced. In addition, n is a positive number from 0 to 100, and particularly 0.5 to
It is preferably a positive number of 10. When n is larger than 100, the effect of imparting gloss and slipperiness to hair is reduced.

R ¹ in the chemical formula 4 is preferably an alkylene group such as a methylene group, a dimethylene group, a trimethylene group, and a tetramethylene group, and particularly preferably a trimethylene group. In addition, specific examples of R ³ include alkylene groups such as methylene group, dimethylene group, trimethylene group, and tetramethylene group.
In the present invention, it is particularly preferably a dimethylene group.

R ² , R ⁴ and R ⁵ are a hydrogen atom directly connected to a nitrogen atom or a monovalent group represented by the above formula (2), wherein the group represented by the formula (2) is R. ² , R ⁴ and R
It is 30 mol% or more of the total amount of ⁵ , and particularly preferably 50 mol% or more. This is because if it is less than 30 mol%, the dispersibility in an aqueous hair treatment agent is lowered.

Further, b is an integer of 2 to 20, particularly 3
It is preferably from 10 to 10. When b is less than 2, the dispersibility in an aqueous hair cosmetic composition is poor and 20
This is because if it is larger, the slipperiness-imparting effect becomes inferior. Further, c is an integer of 0 to 10, and particularly preferably 0 to 5. This is because when c is greater than 10, the dispersibility in an aqueous hair cosmetic composition is poor.

A specific example of R ⁶ is a hydrogen atom;
Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a heptyl group, and an octyl group; and an acyl group such as an acetyl group and a benzoyl group. Groups and acetyl groups are preferred.

The organopolysiloxane represented by Chemical Formula 4 in the present invention can be obtained by reacting the organopolysiloxane represented by Chemical Formula 5 below with the polyoxyalkylene glycidyl ether represented by Chemical Formula 6 below.

Embedded image However, R in the formula is the same as R in the above chemical formula 4,
Is a monovalent group represented by the following formula (4), Z is R, B or a group represented by the formula (3), m is a positive number from 5 to 500, and n is a positive number from 0 to 100. And if n = 0, then at least one Z is B. ^{(4) -R 1 - (NH} -R 3) a -NH 2 where, R ^1, R ³ and a in the formula is the same as R ^1, R ³ and a in the formula 4.

[0018]

[Chemical 6] However, R ⁶ is R ^6, b and c in the formula in the formula 4,
The same as b and c.

Specific examples of the organopolysiloxane represented by the above chemical formula 5 used in the present invention include compounds represented by the following chemical formula 7.

Embedded image However, m and n in the formula are the same as m and n in the above chemical formula 4.

Specific examples of the polyoxyalkylene glycidyl ether represented by the above chemical formula 6 used in the present invention include compounds represented by the following chemical formula 8.

Embedded image However, b and c in the formula are the same as b and c in the above chemical formula 4.

In the present invention, the content of the essential organopolysiloxane in the hair cosmetic composition is 0.01-1.
It is preferably 0% by weight, and particularly preferably 0.1 to 5% by weight. Further, the addition method, an oil component to be further added if necessary, a method of emulsifying in water, a method of adding and blending to an alcohol solution or an aqueous solution, a method of mixing with an oil component, a powder, etc.,
The selection is made according to the form of the product such as shampoo, milky lotion, and hair styling agent.

The hair cosmetic composition of the present invention contains the organopolysiloxane represented by the above chemical formula 4 as an essential component. Further, depending on the use, various nonionic surfactants, anionic surfactants, Ingredients such as cationic surfactants, amphoteric surfactants, waxes, plant oils and various powders may be added as appropriate. Examples thereof include components containing fatty acid soap, alkylbenzene sulfonate, alkyl sulfate, alkyl ether sulfate, monoglyceride sulfate, alkyl phosphate, methyl tauride, fatty acid alkanolamide, and the like.

When the hair cosmetic composition of the present invention is used in a shampoo for hair of humans or animals, it is preferable to use a fatty alcohol or a fatty alcohol ethoxylate as the above-mentioned additive, especially from lauryl and mistyl alcohol. Derivatives and salts thereof are preferred. Examples of such salts include sodium lauryl sulfate, sodium lauryl ether sulfate, ammonium lauryl sulfate, triethanolamine lauryl sulfate, monoethanolamine lauryl sulfate, and disodium laurylethoxysulfosuccinate.

Since the hair cosmetic composition of the present invention uses a specific organopolysiloxane containing an amino group and a polyoxyalkylene group in its structure, it does not depend on the product form, and the hair has gloss and gloss. It can give suppleness, slipperiness, and a moist feeling. The hair cosmetics can be in the form of an aqueous solution, emulsion, aerosol, solid, paste, powder, etc., and can be used in shampoos, hair conditioners, after-shampoos, conditioners, hair conditioners, set lotions, broth styling lotions, prestresses. Shampoo treatment, hair spray, hair styling gel, hair dye, hair bleach, first permanent wave agent,
Permanent wave second agents, and hair styling agents such as hair dyes, hair liquids, hair tonics and the like can be mentioned.

[0025]

BEST MODE FOR CARRYING OUT THE INVENTION The hair cosmetic composition of the present invention can be used as an emulsion, a solution paste, or a spray, together with a known additive or solvent to which the organopolysiloxane represented by Chemical Formula 4 is added, if necessary. It can be easily obtained by mixing and preparing.

[0026]

EFFECTS OF THE INVENTION The hair cosmetic composition of the present invention has excellent product stability because it contains an aminoalkyl-modified organopolysiloxane having a special structure. In addition, the treated hair has gloss, suppleness, slipperiness,
A moist feeling and a light brushing property can be imparted.

[0027]

EXAMPLES The present invention will be described in more detail with reference to the following Examples, but it should not be construed that the invention is limited thereto.
Unless otherwise specified, "%" and "parts" described below mean "% by weight" and "parts by weight". The viscosity is a value measured at 25 ° C.

Synthesis Example 1 In a 500 ml separable flask equipped with a stirrer, a thermometer, a reflux cooling device, and a nitrogen gas inlet tube, an aminoalkyl group-containing organopolysiloxane A (molecular weight 2,056) 61.
7 g, 36.4 g of polyoxyalkylene glycidyl ether A (molecular weight 404) represented by the following chemical formula 10 (100 mol% based on the total NH in the aminoalkyl group-containing organopolysiloxane), and isopropyl alcohol 9
Charge 8.0 g, stir while introducing nitrogen gas, and
When the low boiling point fraction was removed at 00 ° C. for 1 hour, 9
2.8 g of organopolysiloxane-1 having a viscosity of 190 cP and represented by the following chemical formula 11 was obtained.

[0029]

Embedded image

Embedded image

[0030]

Embedded image However, R in the formula is a group represented by the following chemical formula 12.

Embedded image

The aminoalkyl group-containing organopolysiloxane A represented by the chemical formula 9 above, dimethylpolysiloxane used in Comparative Example 1 to be described later, and the obtained organopolysiloxane-1, 1% for each 20 parts It was dispersed in 80 parts of an aqueous acetic acid solution (about 1 equivalent of acetic acid / nitrogen atom), and the water dispersibility of the resulting aqueous solution was visually observed and evaluated as follows. The results are as shown in Table 1.

Evaluation Criteria : Solution becomes transparent ◯ (water dispersibility is good) Solution is suspended ・ ・ ・ △ (water dispersibility is slightly bad) Dissolution is not possible ・ ・ ・・ ・ ・ ・ ・ ・ × (insoluble)

[Table 1]

Synthesis Example 2. The amount of the polyoxyalkylene glycidyl ether A represented by Chemical formula 10 is 24.2 g.
The reaction was carried out in the same manner as in Synthesis Example 1 except that the amount was (67 mol% based on the total NH in the aminoalkyl group-containing organopolysiloxane A).
P organopolysiloxane-2 was obtained. The obtained organopolysiloxane-2 was evaluated for water dispersibility in exactly the same manner as in Synthesis Example 1, and the results are shown in Table 1.

Synthesis Example 3. 51.4 g of an aminoalkyl group-containing organopolysiloxane A represented by Chemical Formula 9 and the following Chemical Formula 1
Same as Synthesis Example 1 except that 48.8 g of polyoxyalkylene glycidyl ether B (molecular weight 650) represented by 3 (100 mol% relative to total NH in aminoalkyl group-containing organopolysiloxane A) was used. And the reaction was carried out to obtain 91.0 g of organopolysiloxane-3. The results of evaluating the water dispersibility of the obtained organopolysiloxane-3 in the same manner as in Synthesis Example 1 are shown in Table 1.
As shown in FIG.

Embedded image

Synthesis Example 4. Organopolysiloxane-4 was prepared in the same manner as in Synthesis Example 1 except that the aminoalkyl group-containing organopolysiloxane represented by Chemical formula 9 and the glycidyl alcohol represented by Chemical formula 14 below were used.
I got The results of evaluating the water dispersibility of the obtained organopolysiloxane-4 in the same manner as in Synthesis Example 1 are as shown in Table 1.

Embedded image

Examples 1, 2 and Comparative Example 1. A shampoo was prepared by the usual preparation method using the compositions shown in Table 2. With respect to the obtained shampoo, the results of observing the foaming property, drying property and slipperiness during hair washing are as shown in the same table.

[Table 2]

Examples 3, 4 and Comparative Example 2. An oil rinse was prepared by the usual preparation method using the compositions shown in Table 3. The results of observing the appearance, the hair treatment, and the slipperiness of the dried hair of the obtained oil rinse are as shown in the same table.

[Table 3]

Examples 5 and 6 and Comparative Example 3. A styling gel was prepared by the usual preparation method using the compositions shown in Table 4. With respect to the obtained styling gel, the results of observing the luster and smoothness when the hair is treated are as shown in the same table.

[Table 4]

Claims (2)

[Claims] 1. A hair cosmetic composition comprising an organopolysiloxane represented by the following chemical formula 1; However, in the formula, R is a monovalent hydrocarbon group having 1 to 20 carbon atoms, A is a monovalent group represented by the following formula (1), and X is R or A.
Alternatively, a monovalent group represented by the following formula (3), m is 5 to 500
, N is a positive number from 0 to 100, and when n = 0, X
At least one of them is A; (1) -R ^1- (NR ² -R ³ ) _a -NR ⁴ R ⁵ where R ¹ is a divalent hydrocarbon group having 1 to 8 carbon atoms. , R ² , R ⁴ and R ⁵ are hydrogen atoms directly connected to a nitrogen atom or a monovalent group represented by the following formula (2), wherein the group represented by the formula (2) is R ² , R ⁴ And ³ of the total amount of R ⁵
0 mol% or more, R ³ is a divalent hydrocarbon group having 1 to 4 carbon atoms, and a is an integer of 0 to 4; (2) -CH ₂ CH (OH) CH ₂ (OC ₂ H ₄ ) _b (OC ₃ H ₆ ) _c OR ⁶ wherein R ⁶ is a hydrogen atom or a monovalent hydrocarbon group having 1 to 8 carbon atoms, and a monovalent group selected from an acyl group. , B is an integer of 2 to 20 and c is an integer of 0 to 10; (3) -OR ⁷ wherein R ⁷ is a hydrogen atom or a monovalent hydrocarbon group having 1 to 8 carbon atoms. is there. 2. The organopolysiloxane represented by Chemical formula 1 is a reaction product of an organopolysiloxane represented by Chemical formula 2 below and a polyoxyalkylene glycidyl ether represented by Chemical formula 3 below. Hair cosmetics described in [Chemical Formula 2] However, in the formula, R is a monovalent hydrocarbon group having 1 to 20 carbon atoms, B is a monovalent group represented by the following formula (4), and Z is R or B.
Or a monovalent group represented by —OR ⁷ (wherein R ⁷ is a hydrogen atom or a monovalent hydrocarbon group having 1 to 8 carbon atoms), and m is 5
~ 500 positive number, n is 0-100 positive number, n = 0
And at least one Z is B; (4) -R ^1- (NH-R ³ ) _a -NH _{2 wherein} R ¹ is a divalent hydrocarbon group having 1 to 8 carbon atoms, R ³ is a divalent hydrocarbon group having 1 to 4 carbon atoms, and a is an integer of 0 to 4; However, R ⁶ in the formula is a monovalent group selected from a hydrogen atom or a monovalent hydrocarbon group having 1 to 8 carbon atoms, and an acyl group, b is an integer of 2 to 20, and c is 0. It is an integer of -10.