JPH04112814A - Hair-treatment agent composition - Google Patents

Abstract

PURPOSE:To provide a hair-treatment agent composition containing a silicone modified with a cyclic Bunte salt and an oxidizing agent and effective in imparting hair with split-prevention effect and luster durable over a long period. CONSTITUTION:The objective composition contains 0.01-50wt.% of a cyclic Bunte salt-modified silicone of formula I (X is alkali metal, alkaline-earth metal, ammonia, amine or quaternary ammonium salt; n is 4-10; m is 3-11) and 0.05-30wt.% of an oxidizing agent (e.g. hydrogen peroxide). More desirably, the composition is produced by compounding 0.1-50wt.% of compounds of formula II and formula III (R is H, 1-4C alkyl, etc.; Y is H or OH; p, q and r are 0-5; R3 is 8-18C alkyl) and properly compounding conventional components for hair-treatment. The composition is used in the form of two-pack type composition consisting of the 1st agent containing the compound of formula I and the 2nd agent containing the oxidizing agent.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a hair treatment composition that can impart long-lasting split-end prevention effects and shine to hair.

(Prior art) Hair treatment agents for the purpose of preventing split ends of hair have conventionally been formulated with polymeric silicone (Japanese Patent Application Laid-Open No. 1-273
No. 513), etc., which attempts to prevent split ends/hair breakage during the brushing process by improving the slippage of the hair surface.

[Problem to be solved by the invention]

However, in all of the above-mentioned conventional hair treatment agents, the conditioning ingredients are simply adsorbed to the hair surface by physical adsorption, so the conditioning ingredients tend to fall off with shampoo after being applied to the hair, and the conditioning ingredients are easily removed from the hair by shampooing. However, there is a problem in that it cannot provide a long-lasting split-end prevention effect and shine.

Therefore, an object of the present invention is to provide a hair treatment composition that can impart long-lasting split-end prevention effects and shine to hair.

[Means for Solving the Problems] As a result of intensive research to achieve the above object, the present inventors found that a cyclic Bunte salt-modified silicone represented by the following general formula (I) can be used in combination with an oxidizing agent to affect hair. By applying
It has been found that it is possible to impart long-lasting split-end prevention effects and shine to hair.

CHz CH-OR CHz-3t(hX (In the above general formula (I), X represents an alkali metal, alkaline earth metal, ammonia, amine or quaternary ammonium salt, n is an integer of 4 to 10, m is is an integer from 3 to 11.] The present invention was made based on the above findings, and includes (a)
One or more cyclic Bunte salt-modified silicones represented by the above general formula (+), and (b) one or two oxidizing agents.
The present invention provides a hair treatment composition characterized in that it contains at least one species.

Hereinafter, the hair treatment composition of the present invention will be explained in detail.

Cyclic Bunte salt-modified silicone represented by the general formula (I) used in the present invention (hereinafter referred to as cyclic silicone)
Examples of the alkali metal represented by X include sodium, potassium, lithium, etc., examples of the alkaline earth metal include magnesium, calcium, etc., and examples of the amine include ammonium, monoethanolamine, jetanolamine, Examples of quaternary ammonium salts include mono- or di-long-chain alkyl quaternary ammonium salts having branched or straight-chain alkyl groups, and polyoxyalkylene adducts thereof. can be mentioned.

The above-mentioned cyclic silicone is preferably one in which n in the general formula (I) is 4 to 6.

The content of the cyclic silicone in the composition is preferably 0.01 to 50% by weight, more preferably 0.1 to 20M.
The amount is %.

In addition, examples of the oxidizing agent used in the present invention include peroxides such as hydrogen peroxide, sodium percarbonate, and sodium perborate, and bromates such as sodium bromate and potassium bromate. Hydrogen and sodium bromate are preferred.

The content of the oxidizing agent in the composition is preferably 0.05
-30% by weight, more preferably 0.5-10% by weight.

The hair treatment composition of the present invention also contains the following general formula (I
It is preferable to blend one or more of the compounds represented by t) or CDI).

(CL), y (J: In the general formula (■), R is a hydrogen atom, R, -φR
,,R, -φ or a linear or branched lower alkyl group having 1 to 4 carbon atoms, R1 represents a hydrogen atom, a methyl group or a methoxy group, and R2 represents -CH.

C(CH,), -1-CH2-CH(CH,)- or -
Indicates CH=CHCHHz-. Further, Y represents a hydrogen atom or a hydroxyl group, p, q and r are each an integer of 0 to 5, and at least one of P and q is 0. ) R (In the above general formula (I[[), R1 represents a branched or straight chain alkyl group having 8 to 18 carbon atoms.) Examples of the compound represented by the above general formula (U) include Eba, Examples include isopropyl alcohol, ethyl alcohol, benzyl alcohol, and the like, with ethyl alcohol and benzyl alcohol being particularly preferred.

Moreover, as a compound represented by the above general formula (lII), one in which R1 is an alkyl group having 8 to 12 carbon atoms is preferable.

The content of the compound represented by the above general formula ([[) or (I[l)] in the composition is preferably 0.1 to 50% by weight,
More preferably, it is 0.5 to 50% by weight.

The compound represented by the above general formula (II) or (I[l) significantly increases the permeation and adsorption of the above-mentioned cyclic silicone to the hair, and particularly in damaged areas such as the ends of hair and permed hair, the permeation and adsorption makes it more sustainable. It can impart a natural split-end prevention effect and shine.

In addition, the hair treatment composition of the present invention may include, if necessary,
Ammonia, amino compounds, amines and quaternary ammonium salts can be blended.

The above amino compounds include cysteine, arginine,
Examples of amines include triethanolamine, jetanolamine, monoethanolamine, etc., and examples of quaternary ammonium salts include stearyltrimethylammonium chloride and branched or straight chain alkyl salts. Examples thereof include mono- or di-long chain alkyl quaternary ammonium salts and polyoxyalkylene adducts.

Furthermore, the hair treatment composition of the present invention may contain surfactants, polymer compounds, oils, polyhydric alcohols, and other ingredients that are usually applied to hair cosmetics depending on the purpose, use, split mold, etc. It can also be blended as appropriate, and the remainder other than these components is water.

The surfactants include linear or branched alkyl hanzene sulfonates, alkyl or alkenyl ether sulfates with ethylene oxide and/or propylene oxide added, olefin sulfonates, alkanesulfonates, saturated or unsaturated Fatty acid salt, alkyl or alkenyl ether carboxylate with ethylene oxide and/or propylene oxide added, α-sulfo fatty acid salt ester, amino acid type surfactant, sulfosuccinic acid type surfactant, phosphate ester type surfactant, sulfone Acid type amphoteric surfactant, hetain type amphoteric surfactant, alkylamine oxide, cationic surfactant, Po1! Oxyalkyl or alkenyl ether, polyoxyalkylphenyl ether, higher fatty acid alkanolamide or alkylene oxide adduct, ester of polyhydric alcohol and fatty acid, ester of sorbitol and fatty acid, ester of sucrose and fatty acid, ether of higher alcohol and sugar, etc. can be mentioned. Moreover, as the above-mentioned polymer compound,
Cationized cellulose derivatives, cationic starches, cationized guar gum derivatives, copolymers of diallyl quaternary ammonium salts and acrylamide, quaternized polyvinylpyrrolidone derivatives and polyglycolamine condensates, carboxyvinyl polymers, xanthan gum, methylcellulose, hydroxyethylcellulose etc. Also,
The above-mentioned oils include higher fatty acids such as stearic acid, higher alcohols such as cetanol, solid fats such as cholesterol, petrolatum, and cholesteryl isostearate, liquid oils such as squalene and jojoba oil, and cyclic silicones other than the above-mentioned cyclic silicone used in the present invention. Examples include silicone derivatives. Further, as the polyhydric alcohol, glycerin, 1.3
-Butylene glycol, propylene glycol, dipropylene glycol, polyethylene glycol, sorbitol and the like. In addition, the other ingredients listed above include various medicinal agents, chelating agents, the other side of the pearl, fragrances, pigments, ultraviolet absorbers, disinfectants such as triclosan and trichlorocarpan, and anti-inflammatory agents such as potassium glycyrrhizinate and tocopherol acetate. , anti-dandruff agents such as zinc pyrithione and piroctone auramine, and preservatives such as methylparaben and butylparahen.

The hair treatment composition of the present invention is usually in the form of a two-part composition comprising, for example, a first part containing the above-mentioned cyclic silicone or the above-mentioned oxidizing agent, and a second part containing the remaining compound. Either the first agent or the second agent is applied to the hair and then the other is applied, or the first agent and the second agent are mixed immediately before use and then applied to the hair. used.

Further, the hair treatment composition of the present invention can be used as shampoo, rinse, treatment, styling agent, permanent waving agent, hair color, bleaching agent, and the like.

[Effect]

When the hair treatment composition of the present invention is applied to hair and allowed to dry as is, or after rinsing and drying the hair, the conditioning component penetrates and adsorbs into the damaged areas of the hair surface layer, resulting in a long-lasting effect. A film-like coating can be formed on the surface layer of the hair, and a long-lasting split-end prevention effect and shine can be imparted to the hair.

The cyclic Bunte salt-modified silicone represented by the general formula (I) used in the present invention is a new compound, and can be produced, for example, as follows.

First, monomethylcyclopolysiloxane and allyl glycidyl ether are reacted.

This reaction is catalyzed by chloroplatinic acid, a platinum catalyst supported on carbon or alumina, a platinum olefin complex, or a phosphine complex. It is also catalyzed by complexes of Group I transition metal elements. The above reaction is carried out in the presence of these catalysts at a temperature of about room temperature to about 200°C for about 0.5 to 10 hours. Moreover, the ratio (molar ratio) of both used in this case is preferably monomethylcyclopolysoloxane:allyl glycidyl ether-1:1 to I:10.

Next, the reaction product obtained in the above reaction is treated with thiosulfate to open the epoxy ring of the reaction product.

This ring-opening reaction is carried out using a phase transfer catalyst, such as the following formula (IV).
In the presence of the compound represented by, using a solvent such as a mixed solvent of water and ethanol, a mixed solvent of water and ituburobanol,
The thiosulfate is allowed to act on the reaction product for about 0.5 to 24 hours at a temperature ranging from room temperature to reflux. Also, at this time, since the pH of the reaction solution increases, the HCffi solution,
H2SO, solution, H, PO.

It is preferable to carry out the reaction while maintaining the pH within 5 to 9 using a solution or the like. Further, the usage ratio (molar ratio) of the above reaction product and the above thiosulfate is as follows: reaction product:thiosulfate=I
:1 to 1:3 is preferable.

H2 H-OH CI! , -OH Thus, the general formula (I) used in the present invention
A cyclic Bunte salt-modified silicone can be obtained.

[Examples] Hereinafter, the present invention will be explained in more detail by giving synthesis examples and examples showing the production of the cyclic silicone used in the present invention together with comparative examples, but the present invention is limited to these examples. It's not a thing.

Synthesis Example 1 (In I, n=4, m=3, C) 1-OH CHz-520Ja (I) 50 g of tetramethylcyclotetrasoloxane and 123.4 g of allyl glycidyl ether are charged into a 300-row flask. While thoroughly stirring, add 30μ of 2% chloroplatinic acid isopropanol solution! Add. After 2 hours, excess allyl glycidyl ether was distilled off from the reaction mixture using one distillation under reduced pressure, resulting in a colorless and transparent liquid.
g was obtained.

This liquid is a silicone compound represented by the following formula (V).

Inclusion of cyclic silicone in which X = sodium (V) CH2 (2) 15 g of the silicone compound obtained in the above (I),
Na25Js・51 (z021.4 g, water 35.2
g, 60.6 g of ethanol, 0.5 g of 8 liquids of 0.1% phenolphthalein, and 0.4 g of the compound represented by the above formula (TV) were placed in a 300 jIf volume three-neck flask, and heated to 80°C with stirring. . During the reaction, the pH increases, but the reaction is continued while being neutralized with 10% 1 (CI!, Pjj solution).The reaction is completed in 2 hours.Then, water is distilled off from the reaction solution under reduced pressure, and 500 IIl of ethanol is added. Add and heat.

Insoluble salts were filtered off and the filtrate was concentrated to obtain 26 g of the desired product as a white to pale yellow solid.

The molecular weight and spectral data of the obtained target product were as follows.

・Decomposed at 150°C ・Molecular weight 1241.6 ・Spectrum data' HNMR (MeOH-d,); δ (ppm)
0, 1 (Si-CHs, S, 128) 0, 55
(Si-CHz-, t 8.7)1z, 8)1)1,
53 (Si-CHz-CHz-, m, 88) 3, 0
7 (Si-CHz-CHz-CHz-0-, t 6
Hz, 8H)4,75 (:;CH-OH,m, 4
H)”CNMR(MeOH-d4);δ(pp
s+)1,1 (Si-CHs) 15,0 (Si-CHz-) 25,2 (-cow-) 40,2 (-CHt-5tOxNa>71, a (
〉CHOH) I R (KBr) v max 3446 cm-' (-OH) 1 038 cm-' (Si-0) Example 1 According to the formulation shown in Table 1 below, 2 consisting of the first agent and the second agent Cutting allowance compositions (present invention products 1 to 3 and comparative products 1 to 2) were prepared. These compositions were applied to Japanese black hair perm according to the application method shown in Table 1 below, and the results obtained are shown in Table 1 below.

Example 2 Two-drug compositions (products of the present invention 4 to 6 and comparative products 3 to 4) consisting of a first part and a second part were prepared according to the formulations shown in Table 2 below. These compositions were applied to Japanese black hair perm according to the application method shown in Table 2 below, and the results obtained are shown in Table 2 below.

[Effects of the Invention] According to the hair treatment composition of the present invention, the conditioning component penetrates and adsorbs into the surface layer of the hair, and a continuous film-like film is formed on the surface layer of the hair. It can provide long-lasting split-end prevention effect and shine,
Furthermore, when applied to hair, a more lasting film-like film can be formed on damaged areas of the surface layer of the hair by using a heating device such as a blow dryer during daily care or a heating device at a salon (beauty salon). This can further enhance the effect of preventing split ends and the effect of maintaining gloss.

Claims (1)

[Scope of Claims] (a) one or more cyclic Bunte salt-modified silicones represented by the following general formula (I); and (b) one oxidizing agent.
A hair treatment composition comprising one or more species. ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・(I) [In the above general formula (I), X represents an alkali metal, alkaline earth metal, ammonia, amine, or quaternary ammonium salt, and n is an integer of 4 to 10, and m is an integer of 3 to 11. )