JP2829111B2 - Hair treatment composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a hair treatment composition capable of imparting a long-lasting effect on preventing split ends and a luster to hair.

[Conventional technology]

As a hair treatment agent for the purpose of preventing split ends of hair, those containing a high molecular weight silicone (Japanese Unexamined Patent Publication No. 1-2735)
No. 13) which aims to prevent split ends / cuts in the brushing process by improving the slip on the surface of the hair.

[Problems to be solved by the invention]

However, any of the above-mentioned conventional hair treatment agents,
Since the conditioning component is simply adsorbed on the hair surface only by the physical adsorption action, the conditioning component is easily dropped off by the shampoo after being applied to the hair, and the hair has a long-lasting effect on preventing split ends and gloss. Cannot be granted.

Accordingly, an object of the present invention is to provide a hair treatment composition capable of imparting a long-lasting effect on preventing split ends and luster to hair.

[Means for solving the problem]

The present inventors have conducted intensive studies to achieve the above object. As a result, the cyclic Bunte salt-modified silicone represented by the following general formula (I) was applied to hair in combination with a reducing agent to give long-lasting hair. It was found that the effect of preventing split ends having long-lasting properties and luster can be imparted.

[In the above general formula (I), X represents an alkali metal, alkaline earth metal, ammonium, amine or quaternary ammonium salt, n is an integer of 4 to 10, and m is an integer of 3 to 11. However, when X is an alkaline earth metal, two residues other than X from the compound represented by the general formula (I) are bonded to X. The present invention has been made based on the above findings,
(A) a hair treating agent composition comprising one or more of the cyclic Bunte salt-modified silicone represented by the above general formula (I) and (b) one or more of a reducing agent; It provides things.

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

In the 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 and the like; Examples of the metal include magnesium and calcium, and examples of the amine include ammonium, monoethanolamine, diethanolamine, triethanolamine,
Examples of the quaternary ammonium salt include amino acids and the like, and examples of the quaternary ammonium salt include mono- or di-long-chain alkyl quaternary ammonium salts having a branched or linear alkyl group, and polyoxyalkylene adducts thereof.

As the above-mentioned cyclic silicone, those in which n in the general formula (I) is 4 to 6 are preferable.

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

Examples of the reducing agent used in the present invention include thioglycolic acid and salts thereof (preferred salts are alkali metal salts such as ammonium salt, sodium salt and potassium salt and alkaline earth metal salts such as calcium salt) and cysteine. And salts thereof (preferably salts are hydrochlorides), L-acetylcysteine and salts thereof (preferably salts are hydrochlorides), and the like. In particular, thioglycolic acid, ammonium thioglycolate, cysteine and cysteine Is preferred.

The content of the reducing agent is preferably 0.1 to 2 in the composition.
0% by weight, more preferably 0.5 to 10% by weight.

The hair treatment composition of the present invention preferably contains one or more compounds represented by the following general formula (II) or (III).

(In the general formula (II), R is a hydrogen atom, R ₁ -φ-R ₂ ,
R ₁ -φ represents a linear or branched lower alkyl group having 1 to 4 carbon atoms, R ₁ represents a hydrogen atom, a methyl group or a methoxy group, and R ₂ represents —CH ₂ —, —C (CH ₃ ) _{2 -, - CH 2 -CH (} C
H ₃ ) — or —CH ＝ CH—CH ₂ —. 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. ) (In the general formula (III), R ₃ represents a branched or straight-chain alkyl group having 8 to 18 carbon atoms.) Examples of the compound represented by the general formula (II) include isopropyl alcohol and ethyl alcohol , Benzyl alcohol, and the like, and ethyl alcohol and benzyl alcohol are particularly preferable.

As the compound represented by the general formula (III), those in which R ₃ is an alkyl group having 8 to 12 carbon atoms are preferable.

The content of the compound represented by the general formula (II) or (III) is preferably 0.1 to 50% by weight, more preferably 0.5 to 50% by weight in the composition.

The compound represented by the general formula (II) or (III) is
Remarkably enhances the permeation and adsorption of the above-mentioned cyclic silicone to hair,
In particular, at a damaged site such as a hair tip or perm hair, osmotic adsorption can impart a more sustained effect on preventing split ends and luster.

Further, the hair treatment composition of the present invention may optionally contain ammonia, amino compounds, amines and quaternary ammonium salts. Examples of the amino compound include cysteine, arginine, glycine, and glutamic acid. Examples of the amines include triethanolamine, diethanolamine, and monoethanolamine. Examples of the quaternary ammonium salt include stearyltrimethylammonium chloride. And mono- or di-long-chain alkyl quaternary ammonium salts having a branched or linear alkyl group, and polyoxyalkylene adducts.

Further, in the hair treatment composition of the present invention, a surfactant, a polymer compound, an oil component, a polyhydric alcohol, and other components which are usually applied to hair cosmetics, depending on the purpose, use, dosage form, etc. They can be appropriately blended, and the balance other than these components is water.

Examples of the surfactant include a linear or branched alkylbenzene sulfonate, an alkyl or alkenyl ether sulfate to which ethylene oxide and / or propylene oxide is added, an olefin sulfonate, an alkane sulfonate, a saturated or unsaturated fatty acid salt. Alkyl or alkenyl ether carboxylate to which ethylene oxide and / or propylene oxide is added, α-sulfofatty acid salt ester, amino acid type surfactant, sulfosuccinic acid type surfactant, phosphate ester type surfactant, sulfonic acid type Amphoteric surfactant, betaine-type amphoteric surfactant, alkylamine oxide, cationic surfactant, polyoxyalkyl or alkenyl ether, polyoxyalkylphenyl ether, higher fatty acid alkanolamide or alkylene oxide Id adducts, esters of polyhydric alcohols and fatty acids, esters of sorbitol and fatty acids, esters of sucrose with fatty acids, ethers of higher alcohols and sugar and the like. Further, as the polymer compound,
Cationized cellulose derivative, cationic starch, cationized guar gum derivative, copolymer of diallyl quaternary ammonium salt and acrylamide, quaternized polyvinylpyrrolidone derivative and polyglycolamine condensate, carboxyvinyl polymer, xanthan gum, methylcellulose, hydroxyethylcellulose And the like. Further, as the oil, higher fatty acids such as stearic acid,
Examples include higher alcohols such as cetanol, solid fats such as cholesterol, petrolatum and cholesteryl isostearate, liquid oils such as squalene and jojoba oil, and silicone derivatives other than the above-mentioned cyclic silicone used in the present invention. Further, as the polyhydric alcohol, glycerin,
Examples thereof include 1,3-butylene glycol, propylene glycol, dipropylene glycol, polyethylene glycol, and sorbitol. In addition, as the other components, various medicinal agents, chelating agents, perming agents, fragrances,
Dyes, UV absorbers, antioxidants, bactericides such as triclosan and trichlorocarban, anti-inflammatory agents such as potassium glycyrrhizinate and tocopherol acetate, anti-dandruff agents such as zinc pyrithione and pyrocton auramine, and preservatives such as methylparaben and butylparaben Agents and the like.

The hair treatment composition of the present invention is usually provided in the form of a two-part composition composed of, for example, a first part containing the above-mentioned cyclic silicone and a second part containing the above-mentioned reducing agent, It is used by applying either the first agent or the second agent to the hair and subsequently applying the other, or by mixing the first agent and the second agent immediately before use and applying the mixture to the hair.

In addition, the hair treatment composition of the present invention is used as a shampoo, a rinse, a treatment, a styling agent, a permanent waving agent, a hair color, a bleaching agent and the like.

[Action]

When the hair treatment composition of the present invention is applied to the hair and dried as it is, or when the hair is dried after rinsing, the conditioning component permeates and adsorbs to the damaged site on the surface layer of the hair, and a continuous film is obtained. Can be formed on the surface layer of the hair, and can impart a long-lasting effect on preventing split ends and luster to the hair.

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

First, monomethylcyclopolysiloxane is reacted with allyl glycidyl ether.

This reaction is catalyzed by chloroplatinic acid, a platinum catalyst supported on carbon, alumina or the like, an olefin complex of platinum, and an osphin complex. It is also catalyzed by a complex of a Group VIII transition metal element. The above reaction is carried out in the presence of these catalysts at a temperature from room temperature to about 200 ° C. for about 0.5 to 10 hours. In this case, the use ratio (molar ratio) of both is preferably monomethylcyclopolysiloxane: allyl glycidyl ether = 1: 1 to 1:10.

Next, a thiosulfate is allowed to act on the reaction product obtained by the above reaction to open the epoxy ring of the reaction product.

This ring opening reaction is carried out by a phase transfer catalyst such as the following formula (IV)
In the presence of a compound represented by, water and ethanol mixed solvent, using a solvent such as water-isopropanol mixed solvent,
The reaction is performed at a temperature of about room temperature to about reflux for about 0.5 to 24 hours by allowing the above thiosulfate to act on the above reaction product. At this time, since the pH of the reaction solution increases, it is preferable to carry out the reaction while maintaining the pH within 5 to 9 using an HCl solution, an H ₂ SO ₄ solution, an H ₃ PO ₄ solution, or the like. Further, the use ratio (molar ratio) of the above reaction product and the above thiosulfate is preferably reaction product: thiosulfate = 1: 1 to 1: 3.

Thus, the cyclic Bunte salt-modified silicone represented by the general formula (I) used in the present invention can be obtained.

〔Example〕

Hereinafter, the present invention will be described in more detail with reference to 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 not limited to these Examples.

Synthesis Example 1 Synthesis of a cyclic silicone in which n = 4, m = 3, and X = sodium in the general formula (I) (1) 50 g of tetramethylcyclotetrasiloxane and 123.4 g of allyl glycidyl ether are charged into a 300 ml three-neck flask. While sufficiently stirring, 30 μ of a 2% solution of isopropanol chloroplatinate is added. After 2 hours, excess allyl glycidyl ether was distilled off from the reaction mixture by vacuum distillation to obtain 120 g of a colorless and transparent liquid. This liquid is a silicone compound represented by the following formula (V).

(2) 15 g of the silicone compound obtained in the above (1), Na _{2
S 2 O 3 · 5H 2 O21.4g} , water 35.2 g, ethanol 60.6 g, was charged with compound 0.4g represented 0.1% phenolphthalein solution 0.5g and the formula (IV) in 300ml capacity three-necked flask, 80 ° C
And stir. During the reaction, the pH rises, but the reaction is continued while neutralizing the solution with 10% HCl. The reaction is completed in 2 hours. Then, water is distilled off from the reaction solution under reduced pressure, and 500 ml of ethanol is added and heated. The insoluble salt was removed by filtration, and the filtrate was concentrated to obtain 26 g of the target substance as a white to pale yellow solid.

The molecular weight and spectrum data of the obtained target product are as follows:
It was as follows.

Decomposes at 150 ° C Molecular weight 1241.6 Example 1 According to the formulation shown in Table 1 below, a two-part composition comprising a first part and a second part (products 1 to 3 of the present invention and comparative products 1 to 2)
Was prepared respectively. These compositions were applied to Japanese black permed hair by the application method shown in Table 1 below, and the obtained effects are shown in Table 1 below.

Example 2 According to the formulation shown in Table 2 below, a two-part composition comprising a first part and a second part (products 4 to 6 of the present invention and comparative products 3 to 4)
Was prepared respectively. These compositions were applied to Japanese black permed hair by the application method shown in Table 2 below, and the obtained effects are shown in Table 2 below.

(Effect of the Invention) According to the hair treatment composition of the present invention, the conditioning component penetrates and adheres to the surface layer of hair, and a continuous film-like film is formed on the surface layer of hair.
It can provide long-lasting anti-split effect and luster, and when applied to hair, it can be more sustained by using heating equipment such as blows for daily care or heating equipment in salons (beauty salons). A film-like film can be formed on the damaged portion of the hair surface layer, and the effect of preventing split ends and the effect of maintaining gloss can be further enhanced.

Continuation of front page (72) Inventor Akira Kawamata 2606 Akabane, Kaigamachi, Haga-gun, Tochigi Prefecture Kao Inside Tochigi Research Institute, Inc. (58) Fields investigated (Int. Cl. ⁶ , DB name) A61K 7/00

Claims (2)

(57) [Claims] (A) one or more cyclic Bunte salt-modified silicones represented by the following general formula (I); and (b)
A hair treatment composition comprising one or more reducing agents. [In the above general formula (I), X represents an alkali metal, alkaline earth metal, ammonium, amine or quaternary ammonium salt, n is an integer of 4 to 10, and m is an integer of 3 to 11. However, when X is an alkaline earth metal, two residues other than X from the compound represented by the general formula (I) are bonded to X. ] 2. The hair treatment according to claim 1, comprising a two-part composition comprising a first part containing the cyclic Bunte salt-modified silicone and a second part containing the reducing agent. Composition.