CA2066399A1 - Oxidative hair dye with levelling action - Google Patents
Oxidative hair dye with levelling actionInfo
- Publication number
- CA2066399A1 CA2066399A1 CA002066399A CA2066399A CA2066399A1 CA 2066399 A1 CA2066399 A1 CA 2066399A1 CA 002066399 A CA002066399 A CA 002066399A CA 2066399 A CA2066399 A CA 2066399A CA 2066399 A1 CA2066399 A1 CA 2066399A1
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- Prior art keywords
- hair
- hair dyes
- present
- oxidation
- dye
- Prior art date
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4953—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
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- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Management, Administration, Business Operations System, And Electronic Commerce (AREA)
Abstract
The levelling action of oxidative hair dyes containing as the oxidative dye 2,4,5,6-tetraaminopyrimidine, or a derivative thereof, can be improved by the addition of histidine or its salts.
Particularly intense and uniform dyeing of the hair is obtained if, in addition to 0.1-10 % by wt. of histidine, the hair dye contains 0.1-5 % by wt. of N-2-hydroxyethylacetamide.
Particularly intense and uniform dyeing of the hair is obtained if, in addition to 0.1-10 % by wt. of histidine, the hair dye contains 0.1-5 % by wt. of N-2-hydroxyethylacetamide.
Description
2 ~ r, .`) OXIDATIVE XAIR DYE ~ITH LEVELLING ~CTION
This invention relates to oxidation hair dyes contain-ing a 2,4,5,6-tetraaminopyrimidine as primary intermediate component and histidine or a water-soluble salt thereof as an auxiliary for improving the uniformity of hair dyeing.
So-called oxidation dyes, which are formed by oxida-tive development from oxidation dye precursors, play an im-portant par~ in the dyeing of hair. Oxidation hair dyes contain such oxidation dye intermediates together with dye-ing auxiliaries in a cosmetic carrier. The oxidation dye intermediates used are so-called primary intermediates or oxidation bases which form the dyes either with one another or with so-called couplers (color modifiers) under the ef-fect of oxidizing agents. Primary aromatic amines con-~53~
taining another free or substituted amino or hydroxy group in the para or ortho position and also diaminopyridines, heterocyclic hydrazona derivatives, 4-aminopyrazolone de-rivatives and tetraaminopyrimidines are normally used as the primary intermediates. m-Phenylenediamines, m-amino-phenols, resorcinols, naphthols and pyrazolones are used as the so-called couplers.
The dyeing auxiliaries used are, for example, anti-oxidants ~or preventillg premature oxidation, pH regulators, buff~Qrs and llair-cosmetic additives. Suitable carriers ~r2, .-or e~ le, c-~ea~.~s, amul~.ons, gels or even foaming solutions, sha~ oos, aerosols or o~siler pre~arations suit-abl_ for a~lica~loil ~O ~Ah2 ~a~
A particuiarly vaiuable pri.~ary intermediate component 1~ whlch, with At~an~ Xnown couplers, forms a broad spectrum of int~nsi~e c~lcrs with good fast-ess properties is 2,4,5,6-tetraaminopyrimidine and derivatives thereof. Many of the hair colors obtainable with 2,4,5,6-tetraaminopyrimidine have the disadvantage that they are absorbed unevenly onto the hair and, for example, color the more seriously damaged hair ends much more intensively than the less damaged regions of the hair roots.
It has now been found that the uniformity of hair dyeing with oxidation hair dyes containing 2,4,5,6-tetra-2S aminopyrimidine or derivatives thereof as primary inter-mediate component can be considerably improved by an ad-dition of histidine or a water-soluble salt thereof.
The histidine may be used in free form or in the form of salt, for example the carbonate, hydrochloride, sulfate, phosphate, acetate, propionate, lactate or citrate. To ob-tain significant levelling, it is sufficient to add the histidine or a salt thereof to the dye in a quantity of 0.1 to 10% by weight and preferably in a quantity of 1 to 5% by weight, expressed as free histt~ine. (All percentages by weight apply to the percentage content, based on the oxi-dation hair dye according to the invention before addition of an oxidizing agent.) Q~&~g~
Another auxiliary which has proved to be effective in improving the depth of color and uniformity of dyeing is N-(2-hydroxyethyl)-acetamide of which the favorable effect on the intensity and fastness of hair colors is already known from DE 2 942 376 C2. In combination with histidine, how-ever, it produces an overproportional, i.e. synergistic, increase in the depth of color and unifor~ity of the dye finish. The 2-hydroxyethyl acetamide is preferably intro-duced into the oxidation ilair dye in a ~uantity of 0.1 to 5~ by weight. Th2 2,4,5,~-tet~aaminopyri~lidine suitable as primary in~2~ clia~2 co.~lpc~nen~ is `;no~n, or example, from DE 2 3S~ 3~. Ho.iever, ,i,~ raamillopyri~.nidine de-rivatives co ~espoildillg ~o ~;e~eral ~oLn~ ula I:
R~R2N ~ NRsR6 in which Rl to R6 independently of one another represent hydrogen, Cl 4 alkyl groups, or C2_4 hydroxyalkyl groups; or the substituents Rl and R2 or ~3 and R4 or R5 and R6 togeth-er with the nitrogen atom form a morpholine, piperidine, pyrrolidine, or piperazine ring, or salts thereof with inor~anic or or~aric acids, for ex-ample in the form of the hydrochlorides, sulfates, phos-phates, acetates, propionates, lactates, or citrates, are 3S also suitable primary intermediate components.
Suitable couplers are virtually any known color coup-ler compounds which form useful dyes with tetraaminopyrim-idine. Ho~ever, preferred couplers for the oxidation hair dyes according to the invention are resorcinol, methyl re-sorcinol, 2,7-dihydroxynaphth~lene, 2,6-dihydroxy-3,4-di-methyl pyridine, and salts the-eof.
~3~ J
. .
In addition to 2,4,5,6-tetraaminopyrimidine and de-rivatives thereof corresponding to formula I, the hair dyes according to the invention may contain other known pri~ary intermediates which are necessary for modifying the colors and for producing natural-loo~ing color ~ones, for example p-phenylenediamine, p-aminophenol, o-amino~hellol or deriva-tives thereof.
Substantive dyes may additionally be used for toning.
Suitable substantive dyes are, ~or ex.~mple~ ni~rophenylene-diamines, nitroaminophenols, nitrophenols, ~nthraquinone dyes, or indophenols.
The primary intermediates ai~d cou~ is ~r~ erally used in substantially molar ~.a~itie " ~ ou(~h it is not a disadvantage if individua, oxida~ion d~e in~erme~iates are present in excess, so tha~ the ~rimarv lntermediates and couplers may be present in a molar r2t~0 of 1:0.5 to 1:2. 2,4,5,6-Tetraaminopyrimidine and derivatives thereof are preferably present in the hair dyes according to the invention in quantities of 0.1 to 10 millimoles per 100 g of hair dye. In addition to the levelling agents men-tioned, namely histidine and N-(2-hydroxyethyl)-acetamide, the oxidation hair dyes according to the invention may con-tain other dyeing auxiliaries, in_luding in particular - antioxidants, for example sodium sulfite~ ascorbic acid, - alkalizing agents, for example ammonia, alkanolamines, such as mono-, di- and triethanolamine, isopropanol-amine, basic amino acids, such as for example orni-thine and arginine, - buffers, for example ammonium carbonate, ammonium chloride, ammonium sulfate, - complexing agents, for example 1-hydroxyethane-1,1-diphosphonic acid, nitrilotriacetic acid, ethylene-diamine tetraacetic acid, - hair-cosmetic auxiliaries, for example water-soluble cationic polymers, glucose, D-panthenol, protein de-rivatives, cholesterol, r ~.
- solubilizers, for example isopropanol, 1,2-propylene glycol, glycerol, - substantive hair dyes, for example nitrophenylene-diamines, nitroaminophenols and anthraquinone dyes.
To produce the oxidation hair dyes according to the invention, the oxidation dye intermediates and the dyeing auxiliaries are incorporated in a suitable cos~etic car-rier. Preferred carriers are gels and cream emulsions.
Apart from water, typical constituents o such carriers are soaps, more particularly ammonium oleate; nonionic, ampho-lytic and anionic wetting agents and emulsifl2rs, ~or e~ai~-ple fatty alcohol sulfates, fatty alcohoi polyglycoi etne~
sulfates, alkanesulfonates, ~-ole~in sul~-on-a~s, e~hvlene oxide adducts with fa~ty alcohols, with fa~ty acids, with alkylphenols, with glycerol and sorbitan fatty acid partial esters; fatty acid alkanolamides and fatty components, for example C12_22 fatty alcohols, paraffin oils. or fatty acid esters; water-soluble thickening agents, for example methyl or hydroxyethyl cellulose, starch, carboxymethyl cellulose, guar, vegetable gums and synthetic water-soluble polymers having a thickening effect; and perfume oils.
In one particularly preferred embodiment, the hair dye according to the invention is in the form of a cream emul-sion containing 0.1 to 25% by weight of a fatty component, O.S to 30% by weight of an emulsifier from the group of anionic, nonionic, zwitterionic or ampholytic surfactants, 0.1 to 10 millimoles per 100 g of primary intermediate com-ponents and 0.1 - 10 millimoles per 100 g of coupler com-ponents and also typical dyeing auxiliaries. The histidine is present in a quantity of 0.1 to 10% by weight.
In principle, the dye may be oxidatively developed with atmospheric oxygen. However, a chemical oxidizing agent is preferably added shortly before application of the dye, particularly in cases where hair is not only to be dyed, but also lightened. Suitable oxidizing agents are, in particular, hydrogen peroxide or adducts thereof with urea, melamine, or sodium borate and also mixtures of such 3.J ~
hydrogen peroxide adducts.
The hair dyes according to the invention are preferab-ly applied at pH values in the range from 6 to 10, irre-spective of their cosmetic formulation, for example in the form of a cream, gel or shampoo. In a particularly pre-ferred embodiment, the hair dyes are applied in a mildly alkaline medium. The application temperatures are in the range from l~ to 40 C. After a contact time of about 30 minutes, the hair dye is removed by washing from the hair to be dyed. The hair is then washed with a ~ild shampoo and dried. There is no need for shampooing in cases where a carrier of high surfactant content, for example a dye shampoo, ~as been used.
The following Examples are intended to illustrate t~.e invention without limiting it in any way.
Examples Hair dyes according to the invention were prepared in the form of a hair dye cream emulsion. Hair strands of which the lower parts had not been pretreated while the upper parts had been predamaged under defined conditions were dyed with the cream emulsion and the color differences between the damaged and undamaged hair regions were meas-ured and evaluated by computer.
1. Preparation of the hair dye cream emul~ion The hair dye cream emulsions, of which the composi-tions are shown in Table 1, were prepared as follows: The fatty alcohols were melted and emulsified with the fatty alcohol ether sulfate and 30 g of water at 90 C. The emulsion was cooled to 60 C. The ascor~ic acid and the histidine dissolved in 20 g of water at 90 C were then added. The oxidation dye intermediates were then dissolved in 10 g of water at 90 C, adjusted with concentrated am-monia to pH 9.5, and added. After cooling to 30 C, the other components were added in the order indicated, the emulsions were adjusted to pH 9.5 with concentrated ammonia solution, made up with water to 100 g, and homogenized.
For comparison, the formulations were also prepared J
without histidine (instead of histidine, a corresponding quantity of water was added).
~air dyeing Oxidative development of the hair dye was carried out S with 6% hydrogen peroxide solution as oxidizing agent. To this end, 50 g of hydrogen peroxide solution (6%) were add-ed to and mixed with 100 g of the emulsion. The ready-to-use dye preparations were then applied to about 15 cm long strands of hair ~eighing about 2 g which had been pre-treated as follot~s:
The upper half of the hair strands (in the region ofthe ends) ~ere treated for 30 minutes with an a~ueous solu-~ion of a cold-wave preparation based on ammonium thiogly-colate. After fixing (10 minutes, potassium bromate solu-~ion), the s2me half of the hair strands was "ultra-bleach~d'` Wit}l an aqueous solution of hydrogen peroxide and ammonium peroxydisulfate, followed ~by another treatment with the cold wave preparation, fixing and ultrableaching.
The lower half of the hair strands (root area) was ultra-bleached only once. In this way, the hair strands weredamaged to different extents in each half.
The dye creams were then left on the hair strands for about 30 minutes at 27 C and subsequently washed out with water. After rinsing with water, the strands were then dried.
3 . Deter~ination of the uniformity of ha~ r dyeing by measurement of the color difference values (DE values) Each hair strand was measured at eight places (four in the region of the root and four in the region of the end) using a Datacolor color measuring system. To this end, the sample to be measured was fixed in a clamp to a spectro-photometer and the remission values were measured over the visible light range of 390 to 700 nm at intervals of 10 nm and evaluated by a computer (HP 2113 E minicomputer). The computer program determines the standard color values under the CIE system (Commission Internationale de l'Eclairage) in accordance with DIN 5033 and converts them into color ?
difference figures in accordance with DIN 6174.
In practical hair dyeing with oxidation hair dyes, DE
vales below 12 may be regarded as satisfactory and accept-able providing no difference in color is visible with the naked eye.
The hair strands dyed with the hair dyes of Examples 1 to 5 according to the invention showed no difference in color visible to the naked eye between the relatively ser-iously damaged upper half and the less dama~ed lower half of the strands. The only visible differences were in the int2ns.i~y or ~a~'ler sti^eil-J~h of color.
3 ,i `3 .. ..
Table 1 Composition in g/100 g l 2 3 4 5 Hydr. tallow fatty 6.5 6.5 6.5 6.5 6.5 alcOhol C16/18 Hydr. coconut oil 2.0 2.0 ~.0 2.0 2.0 lOfatty alcohol C12/18 Fatty alcohol Cl2~1~ l ~ 2 E0 sul,ate, ~5.0 25.0 25.025.0 ~5.0 15Na salt, 28~ aqueous solution Water 30 0 l30.0 30 0 l30 ~ 30.0 Histidine ~ o j 1.0 l.0 Ascorbic acid¦ 0.4 ~ o.~ 1 0.4 0.4 0.4 Water20.0 20.0 20.0 20.0 20.0 2,4,5,6-tetraamino-2.082 2.082 2.082 2.082 2.082 pyrimidine Resorcinol_ _ _ 0.220 0.220 2-Nethyl resorcinol0.993 0.496 0.496 _ _ 2,7-Dihydroxy-3,4- _ 0.492 0.492 0.740 0.740 dimethyl pyridine (NH4)2C03 1.0 1.0 1.0 1.0 1.0 Na2S3 0.5 0.5 0.5 0.5 0.5 2-Hydroxyethyl acetamide _¦ - ¦ 0.5 _ 0.5 Conc. ammonia solution to pH 9.5 Water ad 100 g Colors Ma- Coral Coral Henna Henna hog- red red gold gold any DE value (color 4.48 10.77 8.56 10.88 7.22 difference) Comparison DE value 20.01 27.23 27.23 25.56 25.56 without histidine
This invention relates to oxidation hair dyes contain-ing a 2,4,5,6-tetraaminopyrimidine as primary intermediate component and histidine or a water-soluble salt thereof as an auxiliary for improving the uniformity of hair dyeing.
So-called oxidation dyes, which are formed by oxida-tive development from oxidation dye precursors, play an im-portant par~ in the dyeing of hair. Oxidation hair dyes contain such oxidation dye intermediates together with dye-ing auxiliaries in a cosmetic carrier. The oxidation dye intermediates used are so-called primary intermediates or oxidation bases which form the dyes either with one another or with so-called couplers (color modifiers) under the ef-fect of oxidizing agents. Primary aromatic amines con-~53~
taining another free or substituted amino or hydroxy group in the para or ortho position and also diaminopyridines, heterocyclic hydrazona derivatives, 4-aminopyrazolone de-rivatives and tetraaminopyrimidines are normally used as the primary intermediates. m-Phenylenediamines, m-amino-phenols, resorcinols, naphthols and pyrazolones are used as the so-called couplers.
The dyeing auxiliaries used are, for example, anti-oxidants ~or preventillg premature oxidation, pH regulators, buff~Qrs and llair-cosmetic additives. Suitable carriers ~r2, .-or e~ le, c-~ea~.~s, amul~.ons, gels or even foaming solutions, sha~ oos, aerosols or o~siler pre~arations suit-abl_ for a~lica~loil ~O ~Ah2 ~a~
A particuiarly vaiuable pri.~ary intermediate component 1~ whlch, with At~an~ Xnown couplers, forms a broad spectrum of int~nsi~e c~lcrs with good fast-ess properties is 2,4,5,6-tetraaminopyrimidine and derivatives thereof. Many of the hair colors obtainable with 2,4,5,6-tetraaminopyrimidine have the disadvantage that they are absorbed unevenly onto the hair and, for example, color the more seriously damaged hair ends much more intensively than the less damaged regions of the hair roots.
It has now been found that the uniformity of hair dyeing with oxidation hair dyes containing 2,4,5,6-tetra-2S aminopyrimidine or derivatives thereof as primary inter-mediate component can be considerably improved by an ad-dition of histidine or a water-soluble salt thereof.
The histidine may be used in free form or in the form of salt, for example the carbonate, hydrochloride, sulfate, phosphate, acetate, propionate, lactate or citrate. To ob-tain significant levelling, it is sufficient to add the histidine or a salt thereof to the dye in a quantity of 0.1 to 10% by weight and preferably in a quantity of 1 to 5% by weight, expressed as free histt~ine. (All percentages by weight apply to the percentage content, based on the oxi-dation hair dye according to the invention before addition of an oxidizing agent.) Q~&~g~
Another auxiliary which has proved to be effective in improving the depth of color and uniformity of dyeing is N-(2-hydroxyethyl)-acetamide of which the favorable effect on the intensity and fastness of hair colors is already known from DE 2 942 376 C2. In combination with histidine, how-ever, it produces an overproportional, i.e. synergistic, increase in the depth of color and unifor~ity of the dye finish. The 2-hydroxyethyl acetamide is preferably intro-duced into the oxidation ilair dye in a ~uantity of 0.1 to 5~ by weight. Th2 2,4,5,~-tet~aaminopyri~lidine suitable as primary in~2~ clia~2 co.~lpc~nen~ is `;no~n, or example, from DE 2 3S~ 3~. Ho.iever, ,i,~ raamillopyri~.nidine de-rivatives co ~espoildillg ~o ~;e~eral ~oLn~ ula I:
R~R2N ~ NRsR6 in which Rl to R6 independently of one another represent hydrogen, Cl 4 alkyl groups, or C2_4 hydroxyalkyl groups; or the substituents Rl and R2 or ~3 and R4 or R5 and R6 togeth-er with the nitrogen atom form a morpholine, piperidine, pyrrolidine, or piperazine ring, or salts thereof with inor~anic or or~aric acids, for ex-ample in the form of the hydrochlorides, sulfates, phos-phates, acetates, propionates, lactates, or citrates, are 3S also suitable primary intermediate components.
Suitable couplers are virtually any known color coup-ler compounds which form useful dyes with tetraaminopyrim-idine. Ho~ever, preferred couplers for the oxidation hair dyes according to the invention are resorcinol, methyl re-sorcinol, 2,7-dihydroxynaphth~lene, 2,6-dihydroxy-3,4-di-methyl pyridine, and salts the-eof.
~3~ J
. .
In addition to 2,4,5,6-tetraaminopyrimidine and de-rivatives thereof corresponding to formula I, the hair dyes according to the invention may contain other known pri~ary intermediates which are necessary for modifying the colors and for producing natural-loo~ing color ~ones, for example p-phenylenediamine, p-aminophenol, o-amino~hellol or deriva-tives thereof.
Substantive dyes may additionally be used for toning.
Suitable substantive dyes are, ~or ex.~mple~ ni~rophenylene-diamines, nitroaminophenols, nitrophenols, ~nthraquinone dyes, or indophenols.
The primary intermediates ai~d cou~ is ~r~ erally used in substantially molar ~.a~itie " ~ ou(~h it is not a disadvantage if individua, oxida~ion d~e in~erme~iates are present in excess, so tha~ the ~rimarv lntermediates and couplers may be present in a molar r2t~0 of 1:0.5 to 1:2. 2,4,5,6-Tetraaminopyrimidine and derivatives thereof are preferably present in the hair dyes according to the invention in quantities of 0.1 to 10 millimoles per 100 g of hair dye. In addition to the levelling agents men-tioned, namely histidine and N-(2-hydroxyethyl)-acetamide, the oxidation hair dyes according to the invention may con-tain other dyeing auxiliaries, in_luding in particular - antioxidants, for example sodium sulfite~ ascorbic acid, - alkalizing agents, for example ammonia, alkanolamines, such as mono-, di- and triethanolamine, isopropanol-amine, basic amino acids, such as for example orni-thine and arginine, - buffers, for example ammonium carbonate, ammonium chloride, ammonium sulfate, - complexing agents, for example 1-hydroxyethane-1,1-diphosphonic acid, nitrilotriacetic acid, ethylene-diamine tetraacetic acid, - hair-cosmetic auxiliaries, for example water-soluble cationic polymers, glucose, D-panthenol, protein de-rivatives, cholesterol, r ~.
- solubilizers, for example isopropanol, 1,2-propylene glycol, glycerol, - substantive hair dyes, for example nitrophenylene-diamines, nitroaminophenols and anthraquinone dyes.
To produce the oxidation hair dyes according to the invention, the oxidation dye intermediates and the dyeing auxiliaries are incorporated in a suitable cos~etic car-rier. Preferred carriers are gels and cream emulsions.
Apart from water, typical constituents o such carriers are soaps, more particularly ammonium oleate; nonionic, ampho-lytic and anionic wetting agents and emulsifl2rs, ~or e~ai~-ple fatty alcohol sulfates, fatty alcohoi polyglycoi etne~
sulfates, alkanesulfonates, ~-ole~in sul~-on-a~s, e~hvlene oxide adducts with fa~ty alcohols, with fa~ty acids, with alkylphenols, with glycerol and sorbitan fatty acid partial esters; fatty acid alkanolamides and fatty components, for example C12_22 fatty alcohols, paraffin oils. or fatty acid esters; water-soluble thickening agents, for example methyl or hydroxyethyl cellulose, starch, carboxymethyl cellulose, guar, vegetable gums and synthetic water-soluble polymers having a thickening effect; and perfume oils.
In one particularly preferred embodiment, the hair dye according to the invention is in the form of a cream emul-sion containing 0.1 to 25% by weight of a fatty component, O.S to 30% by weight of an emulsifier from the group of anionic, nonionic, zwitterionic or ampholytic surfactants, 0.1 to 10 millimoles per 100 g of primary intermediate com-ponents and 0.1 - 10 millimoles per 100 g of coupler com-ponents and also typical dyeing auxiliaries. The histidine is present in a quantity of 0.1 to 10% by weight.
In principle, the dye may be oxidatively developed with atmospheric oxygen. However, a chemical oxidizing agent is preferably added shortly before application of the dye, particularly in cases where hair is not only to be dyed, but also lightened. Suitable oxidizing agents are, in particular, hydrogen peroxide or adducts thereof with urea, melamine, or sodium borate and also mixtures of such 3.J ~
hydrogen peroxide adducts.
The hair dyes according to the invention are preferab-ly applied at pH values in the range from 6 to 10, irre-spective of their cosmetic formulation, for example in the form of a cream, gel or shampoo. In a particularly pre-ferred embodiment, the hair dyes are applied in a mildly alkaline medium. The application temperatures are in the range from l~ to 40 C. After a contact time of about 30 minutes, the hair dye is removed by washing from the hair to be dyed. The hair is then washed with a ~ild shampoo and dried. There is no need for shampooing in cases where a carrier of high surfactant content, for example a dye shampoo, ~as been used.
The following Examples are intended to illustrate t~.e invention without limiting it in any way.
Examples Hair dyes according to the invention were prepared in the form of a hair dye cream emulsion. Hair strands of which the lower parts had not been pretreated while the upper parts had been predamaged under defined conditions were dyed with the cream emulsion and the color differences between the damaged and undamaged hair regions were meas-ured and evaluated by computer.
1. Preparation of the hair dye cream emul~ion The hair dye cream emulsions, of which the composi-tions are shown in Table 1, were prepared as follows: The fatty alcohols were melted and emulsified with the fatty alcohol ether sulfate and 30 g of water at 90 C. The emulsion was cooled to 60 C. The ascor~ic acid and the histidine dissolved in 20 g of water at 90 C were then added. The oxidation dye intermediates were then dissolved in 10 g of water at 90 C, adjusted with concentrated am-monia to pH 9.5, and added. After cooling to 30 C, the other components were added in the order indicated, the emulsions were adjusted to pH 9.5 with concentrated ammonia solution, made up with water to 100 g, and homogenized.
For comparison, the formulations were also prepared J
without histidine (instead of histidine, a corresponding quantity of water was added).
~air dyeing Oxidative development of the hair dye was carried out S with 6% hydrogen peroxide solution as oxidizing agent. To this end, 50 g of hydrogen peroxide solution (6%) were add-ed to and mixed with 100 g of the emulsion. The ready-to-use dye preparations were then applied to about 15 cm long strands of hair ~eighing about 2 g which had been pre-treated as follot~s:
The upper half of the hair strands (in the region ofthe ends) ~ere treated for 30 minutes with an a~ueous solu-~ion of a cold-wave preparation based on ammonium thiogly-colate. After fixing (10 minutes, potassium bromate solu-~ion), the s2me half of the hair strands was "ultra-bleach~d'` Wit}l an aqueous solution of hydrogen peroxide and ammonium peroxydisulfate, followed ~by another treatment with the cold wave preparation, fixing and ultrableaching.
The lower half of the hair strands (root area) was ultra-bleached only once. In this way, the hair strands weredamaged to different extents in each half.
The dye creams were then left on the hair strands for about 30 minutes at 27 C and subsequently washed out with water. After rinsing with water, the strands were then dried.
3 . Deter~ination of the uniformity of ha~ r dyeing by measurement of the color difference values (DE values) Each hair strand was measured at eight places (four in the region of the root and four in the region of the end) using a Datacolor color measuring system. To this end, the sample to be measured was fixed in a clamp to a spectro-photometer and the remission values were measured over the visible light range of 390 to 700 nm at intervals of 10 nm and evaluated by a computer (HP 2113 E minicomputer). The computer program determines the standard color values under the CIE system (Commission Internationale de l'Eclairage) in accordance with DIN 5033 and converts them into color ?
difference figures in accordance with DIN 6174.
In practical hair dyeing with oxidation hair dyes, DE
vales below 12 may be regarded as satisfactory and accept-able providing no difference in color is visible with the naked eye.
The hair strands dyed with the hair dyes of Examples 1 to 5 according to the invention showed no difference in color visible to the naked eye between the relatively ser-iously damaged upper half and the less dama~ed lower half of the strands. The only visible differences were in the int2ns.i~y or ~a~'ler sti^eil-J~h of color.
3 ,i `3 .. ..
Table 1 Composition in g/100 g l 2 3 4 5 Hydr. tallow fatty 6.5 6.5 6.5 6.5 6.5 alcOhol C16/18 Hydr. coconut oil 2.0 2.0 ~.0 2.0 2.0 lOfatty alcohol C12/18 Fatty alcohol Cl2~1~ l ~ 2 E0 sul,ate, ~5.0 25.0 25.025.0 ~5.0 15Na salt, 28~ aqueous solution Water 30 0 l30.0 30 0 l30 ~ 30.0 Histidine ~ o j 1.0 l.0 Ascorbic acid¦ 0.4 ~ o.~ 1 0.4 0.4 0.4 Water20.0 20.0 20.0 20.0 20.0 2,4,5,6-tetraamino-2.082 2.082 2.082 2.082 2.082 pyrimidine Resorcinol_ _ _ 0.220 0.220 2-Nethyl resorcinol0.993 0.496 0.496 _ _ 2,7-Dihydroxy-3,4- _ 0.492 0.492 0.740 0.740 dimethyl pyridine (NH4)2C03 1.0 1.0 1.0 1.0 1.0 Na2S3 0.5 0.5 0.5 0.5 0.5 2-Hydroxyethyl acetamide _¦ - ¦ 0.5 _ 0.5 Conc. ammonia solution to pH 9.5 Water ad 100 g Colors Ma- Coral Coral Henna Henna hog- red red gold gold any DE value (color 4.48 10.77 8.56 10.88 7.22 difference) Comparison DE value 20.01 27.23 27.23 25.56 25.56 without histidine
Claims (5)
1. Oxidation hair dyes containing oxidation dye interm-ediates and dyeing auxiliaries in a cosmetic carrier, at least one 2,4,5,6-tetraaminopyrimidine or a derivative thereof or water-soluble salts thereof being present as the primary intermediate component, characterized in that his-tidine or a water-soluble salt thereof is present as a levelling agent.
2. Oxidation hair dyes as claimed in claim 1, charac-terized in that N-2-hydroxyethyl acetamide is present as another dyeing auxiliary.
3. Oxidation hair dyes as claimed in claim 1, charac-terized in that histidine or a salt thereof is present in a quantity of 0.1 to 10% by weight, expressed as free histidine.
4. Oxidation hair dyes as claimed in claim 2, charac-terized in that N-2-hydroxyethyl acetamide is present in a quantity of 0.1 to 5% by weight.
5. Oxidation hair dyes as claimed in claim 1 or 2, characterized in that they contain 2,4,5,6-tetraamino-pyrimidine or derivatives thereof corresponding to the following formula:
in which R1 to R6 independently of one another represent hydrogen, C1-4 alkyl groups, or C2-4 hydroxyalkyl groups; or the substituents R1 and R2 or R3 and R4 or R5 and R6 togeth-er with the nitrogen atom form a morpholine, piperidine, pyrrolidine or piperazine ring, or salts thereof and, as coupler components, one or more compounds from the group consisting of resorcinol, 2-methyl resorcinol, 2,7-dihydroxynaphthalene, 2,6-dihydroxy-3,5-dimethyl pyridine or salts thereof.
in which R1 to R6 independently of one another represent hydrogen, C1-4 alkyl groups, or C2-4 hydroxyalkyl groups; or the substituents R1 and R2 or R3 and R4 or R5 and R6 togeth-er with the nitrogen atom form a morpholine, piperidine, pyrrolidine or piperazine ring, or salts thereof and, as coupler components, one or more compounds from the group consisting of resorcinol, 2-methyl resorcinol, 2,7-dihydroxynaphthalene, 2,6-dihydroxy-3,5-dimethyl pyridine or salts thereof.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3929333.5 | 1989-09-04 | ||
| DE3929333A DE3929333A1 (en) | 1989-09-04 | 1989-09-04 | EQUALIZING OXIDATION HAIR COLORING AGENTS |
| PCT/EP1990/001419 WO1991003230A1 (en) | 1989-09-04 | 1990-08-24 | Oxidative hair dye with levelling action |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2066399A1 true CA2066399A1 (en) | 1991-03-05 |
Family
ID=6388599
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002066399A Abandoned CA2066399A1 (en) | 1989-09-04 | 1990-08-24 | Oxidative hair dye with levelling action |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0491003B1 (en) |
| JP (1) | JPH05500224A (en) |
| KR (1) | KR920702999A (en) |
| AT (1) | ATE119024T1 (en) |
| CA (1) | CA2066399A1 (en) |
| DD (1) | DD297325A5 (en) |
| DE (2) | DE3929333A1 (en) |
| ES (1) | ES2069749T3 (en) |
| FI (1) | FI920898A0 (en) |
| WO (1) | WO1991003230A1 (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE261297T1 (en) * | 1995-06-26 | 2004-03-15 | Hans Schwarzkopf & Henkel Gmbh | HAIR DYE PRODUCT WITH AT LEAST ONE CONDITIONER |
| DE19527124A1 (en) * | 1995-07-25 | 1997-01-30 | Henkel Kgaa | An oxidation |
| JP2002167311A (en) * | 2000-11-30 | 2002-06-11 | Hoyu Co Ltd | Method of hair treatment and hair-treatment agent composition |
| DE102006017901A1 (en) * | 2006-04-13 | 2007-10-25 | Henkel Kgaa | Brightening and / or coloring with improved skin compatibility |
| DE102006020789A1 (en) * | 2006-05-03 | 2007-11-08 | Henkel Kgaa | Brightening and / or coloring agent with imidazoles and aminoalcohols |
| DE102006043920A1 (en) * | 2006-09-14 | 2008-03-27 | Henkel Kgaa | Hydrogen peroxide activation with diones |
| FR2922444B1 (en) | 2007-10-19 | 2014-03-21 | Oreal | COMPOSITION COMPRISING AT LEAST ONE AMMONIUM SALT, AMMONIA AND AT LEAST ONE AMINO ACID |
| US9642788B2 (en) | 2014-04-25 | 2017-05-09 | The Procter & Gamble Company | Shampoo composition comprising gel matrix and histidine |
| US9642787B2 (en) | 2014-04-25 | 2017-05-09 | The Procter & Gamble Company | Method of inhibiting copper deposition on hair |
| US9586063B2 (en) | 2014-04-25 | 2017-03-07 | The Procter & Gamble Company | Method of inhibiting copper deposition on hair |
| EP2937112B1 (en) * | 2014-04-25 | 2019-05-22 | The Procter and Gamble Company | Method of inhibiting copper deposition on hair |
| DE102014225380A1 (en) * | 2014-12-10 | 2016-06-16 | Henkel Ag & Co. Kgaa | Hair colorants containing tetraaminopyrimidine derivatives |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR82354B (en) * | 1978-10-20 | 1984-12-13 | Combe Inc | |
| DE3115643A1 (en) * | 1981-04-18 | 1982-12-16 | Henkel Kgaa | "USE OF DIHYDROXYPYRIDINES AS A COUPLING COMPONENT IN OXIDATION DURANTS AND HAIR COLORING AGENTS" |
-
1989
- 1989-09-04 DE DE3929333A patent/DE3929333A1/en not_active Withdrawn
-
1990
- 1990-08-24 EP EP90914729A patent/EP0491003B1/en not_active Expired - Lifetime
- 1990-08-24 ES ES90914729T patent/ES2069749T3/en not_active Expired - Lifetime
- 1990-08-24 JP JP2513560A patent/JPH05500224A/en active Pending
- 1990-08-24 DE DE59008607T patent/DE59008607D1/en not_active Expired - Fee Related
- 1990-08-24 AT AT90914729T patent/ATE119024T1/en not_active IP Right Cessation
- 1990-08-24 WO PCT/EP1990/001419 patent/WO1991003230A1/en active IP Right Grant
- 1990-08-24 KR KR1019920700481A patent/KR920702999A/en not_active Application Discontinuation
- 1990-08-24 CA CA002066399A patent/CA2066399A1/en not_active Abandoned
- 1990-08-30 DD DD90343749A patent/DD297325A5/en not_active IP Right Cessation
-
1992
- 1992-02-28 FI FI920898A patent/FI920898A0/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE3929333A1 (en) | 1991-03-07 |
| ES2069749T3 (en) | 1995-05-16 |
| EP0491003A1 (en) | 1992-06-24 |
| JPH05500224A (en) | 1993-01-21 |
| FI920898A0 (en) | 1992-02-28 |
| WO1991003230A1 (en) | 1991-03-21 |
| DD297325A5 (en) | 1992-01-09 |
| EP0491003B1 (en) | 1995-03-01 |
| ATE119024T1 (en) | 1995-03-15 |
| DE59008607D1 (en) | 1995-04-06 |
| KR920702999A (en) | 1992-12-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |