JPH0463104B2 - - Google Patents

Description

[Detailed description of the invention]

[Industrial Application Field] The present invention relates to a dyeing composition, and more particularly to a dyeing composition for keratinous fibers that can dye keratinous fibers such as hair with high chroma. [Prior Art] So-called oxidation dyes, which use a combination of a color developer and a coupling substance, have been widely used for dyeing keratinous fibers such as hair. This oxidative dye utilizes the fact that the so-called oxidized dye, which is produced by oxidative coupling of a color developing substance and a coupling substance, strongly dyes hair and the like.
As the color developer, p-phenylenediamine derivatives, diaminopyridine, 4-aminopyrazolone derivatives, heterocyclic hydrazone, etc. are generally used. [Problems to be Solved by the Invention] However, conventional oxidation dyes are still unsatisfactory in saturation, dyeing power, and fastness. [Means for Solving the Problems] The present inventors have made various studies to solve the above-mentioned problems, and as a result, the present inventors have found that by using a specific trifluoromethylated aniline derivative as a color developer, keratinous fibers can be removed. The present invention was completed based on the discovery that it is possible to dye a product with a strong color tone with high saturation, and that the dyeing has excellent fastness. That is, the present invention provides a dyeing composition comprising a color developing substance and a coupling substance, in which the color developing substance is expressed by the following general formula (). (wherein R represents an amino group or a hydroxyl group) A dyeing composition for keratinous fibers is provided, which is characterized by containing a trifluoromethylated aniline derivative or a salt thereof represented by the following formula. Among the trifluoromethylated aniline derivatives () used as color developing substances in the dyeing composition of the present invention, 2-trifluoromethyl-1,
4-diaminobenzene, 3-trifluoromethyl-4-aminophenol or 5-trifluoromethyl-4-aminophenol is preferred. As the salt of the trifluoromethylated aniline derivative (), salts of inorganic or organic acids such as hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, propionic acid, lactic acid, and citric acid are preferable. The trifluoromethylated aniline derivative (), which is a color developer, is a trifluoromethylated p-
It is produced by reducing nitrophenol or p-nitroaniline. Trifluoromethylated p-aminophenols are described, for example, in Journal of Organic Chemistry, No. 27.
Trifluoromethylated p-phenylenediamine is produced by the method described in Kogyo Kagaku Zasshi, Vol. 69, p. 2229 (1966). The coupling substance used in the dye composition of the present invention is not particularly limited as long as it is commonly used in oxidative hair dyes, but examples include α-naphthol, o-cresol, m-cresol,
2,6-dimethylphenol, 2,5-dimethylphenol, 3,4-dimethylphenol, 3,
5-dimethylphenol, benzcatechin, pyrogallol, 1,5- or 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol,
Hydroquinone, 2,4-diaminoanisole, m
-tolylene diamine, 4-aminophenol,
resorcin, resorcin monomethyl ether, m
-phenylenediamine, 1-phenyl-3-methyl-5-pyrazolone, 1-phenyl-3-amino-5-pyrazolone, 1-phenyl-3,5-diketo-pyrazolidine, 1-methyl-7-dimethyl-
Amino-4-hydroxyquinolone-2, 1-amino-3-acetyl-acetamino-4-nitrobenzole or 1-amino-3-cyanoacetyl-
Amino-4-nitro-benzole, m-aminophenol, 4-chlororesorcin, 2-methylresorcin, 2,4-diaminophenoxyethanol, 2,6-diaminopyridine, 3,5-diamino-trifluoromethylbenzene , 2,4-diamino-fluorobenzene, 3,5-diamino-fluorobenzene, 2,4-diamino-6-hydroxypyrimidine, 2,4,6-triaminopyrimidine,
2-amino-4,6-dihydroxypyrimidine,
4-amino-2,6-dihydroxypyrimidine,
4,6-diamino-2-hydroxypyrimidine,
Examples include p-nitro-o-phenylenediamine, 2-amino-5-nitrophenol, p-nitro-m-phenylenediamine, o-nitro-p-phenylenediamine, 2-amino-4-nitrophenol, etc. It will be done. Among these, when using a compound in which R in the general formula () is an amino group as a color developer, 1,3-diaminobenzenes,
2,6-diaminopyridine, phenols; R
When using a compound in which is represented by a hydroxyl group, it is more preferable to use phenols. The mixing ratio of the color developing substance and the coupling substance in the dyeing composition of the present invention may be in excess of one component compared to the other, but the molar ratio should be approximately 1:0.5 to 1:2. is preferred. Further, the color developing substance and the coupling substance can be used alone or in combination of two or more. Further, the dyeing composition of the present invention may contain known color developing substances and ordinary direct dyes, if necessary, in order to obtain a desired color tone. The dyeing composition of the present invention causes oxidative coupling even with oxygen in the air and dyes hair, etc., but it is preferable to cause oxidative coupling by adding a chemical oxidizing agent. Particularly preferred oxidizing agents include hydrogen peroxide; products of addition of hydrogen peroxide to urea, melamine or sodium borate; mixtures of such hydrogen peroxide adducts with potassium peroxide-disulfuric acid, and the like. The dyeing composition of the present invention is usually preferably provided in the form of a cream, emulsion, gel, solution, or the like. In order to form such a dosage form, the color developing substance and the coupling substance should be combined with a wetting or emulsifying agent, a solubilizer, a thickener, a stabilizer, a feel improver, a hair styling base, and a fragrance, which are usually used in the cosmetics field. etc., and may be manufactured according to a conventional method. Wetting or emulsifying agents used here include, for example, alkylbenzene sulfonates, fatty alcohol sulfates, alkyl sulfonates, fatty acid alkanolamides, addition products of ethylene oxide and fatty alcohols, and the like. Examples of thickeners include methylcellulose, starch, higher fatty alcohols, paraffin oil, fatty acids, etc., and examples of stabilizers include reducing agents such as sulfites, hydroquinone derivatives, chelating agents, etc. to improve the feel. As agents and hair styling bases, for example,
Examples include silicones, higher alcohols, oil agents such as various nonionic surfactants, and various cationic polymers. The total amount of the color developing substance and coupling substance in these dosage forms is preferably 0.2 to 5% by weight (hereinafter simply expressed as %), particularly preferably 1 to 3%. It is preferable that the wetting or emulsifying agent is usually blended in an amount of 0.5 to 30%, and the sizing agent is blended in an amount of 0.1 to 25%. In these dosage forms, the pH of the entire composition is preferably adjusted to about 8 to 10. In order to dye horny fibers using the dyeing composition of the present invention, for example, an oxidizing agent is added to the dyeing composition of the present invention to perform oxidative coupling to prepare a dyeing solution, and this dyeing solution is applied to the horny fibers. , 10-50 minutes,
This is preferably carried out by washing the horny fibers for an action time of about 25 to 35 minutes and then drying. Here, the application temperature of the staining solution is 15 to 40°C. [Effects of the Invention] When stratum corneum fibers are dyed using the dyeing composition of the present invention, a wide range of dyeing is possible from yellow to red to blue and even gray to blackish brown due to the combination of color developing substance and coupling substance. High color saturation. Moreover, the obtained color tone has good light fastness, wash resistance and abrasion resistance. [Example] Next, the present invention will be explained in detail with reference to Examples, but the present invention is not limited thereto. Example base composition: (%) Oleic acid 10 Oleic acid diethanolamide 8 Oleyl alcohol 2 Polyoxyethylene octyl dodecyl ether (average addition of 20 moles of EO) 10 Ethanol 15 Propylene glycol 10 Ammonium chloride 3 25% ammonia 7 Water 35 Consists of the above composition 0.01 mol of the color developing substance and 0.01 mol of the coupling substance shown in Table 1 were mixed into 100 g of the base. Then adjust the pH of the composition with ammonia.
The dyeing composition of the present invention was manufactured by adjusting the dyeing composition to 9.5. 6% of the equivalent weight for 100g of the dyeing composition of the present invention
A staining solution was prepared by adding an aqueous hydrogen peroxide solution. Apply this dye solution to human hair with white hair, and dye it at 30℃ for 30 minutes.
Leave it for a minute. The hair was then washed with regular shampoo and dried. Table 1 shows the results of observing the color tone of the obtained dyeing. Color developer P1: 2-trifluoromethyl-1,4-diaminobenzene P2: 3-trifluoromethyl-4-aminophenol P3: 2-trifluoromethyl-4-aminophenol Coupling substance C1: m-phenylene Diamine C2: Resorcinol C3: m-aminophenol C4: p-amino-o-cresol

[Table] Test Example Using the color developing substance and coupling substance shown in Table 2, human hair with gray hair was dyed in the same manner as in the example, and the saturation of the dyed human hair was evaluated according to the following criteria. The results are shown in Table 2. Color developer P1: 2-trifluoromethyl-1,4-diaminobenzene P2: 3-trifluoromethyl-4-aminophenol P3: 2-trifluoromethyl-4-aminophenol PPD: p-phenylenediamine PAP: p-aminophenol coupling substance C1: m-phenylenediamine C4: p-amino-o-cresol Evaluation method ○: Very bright △: Not so bright ×: Not bright

[Table] As is clear from the results in Table 2, the dyeing composition for keratinous fibers of the present invention can dye negative keratin fibers more vividly than the comparative product.

Claims (1)

[Claims] 1. In a dyeing composition comprising a color developing substance and a coupling substance, the color developing substance has the following general formula () (In the formula, R represents an amino group or a hydroxyl group.) A dyeing composition for keratinous fibers, comprising a trifluoromethylated aniline derivative or a salt thereof. 2 The trifluoromethylated aniline derivative is 2-
The dyeing composition according to claim 1, which is selected from trifluoromethyl-1,4-diaminobenzene, 3-trifluoromethyl-4-aminophenol and 2-trifluoromethyl-4-aminophenol. .