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EP1261599A1 - 1,3-diamino-4-heteroaryl-benzol-derivate enthaltende färbemittel für keratinfasern sowie neue 1,3-diamino-4-heteroaryl-benzol-derivate - Google Patents

1,3-diamino-4-heteroaryl-benzol-derivate enthaltende färbemittel für keratinfasern sowie neue 1,3-diamino-4-heteroaryl-benzol-derivate

Info

Publication number
EP1261599A1
EP1261599A1 EP01960727A EP01960727A EP1261599A1 EP 1261599 A1 EP1261599 A1 EP 1261599A1 EP 01960727 A EP01960727 A EP 01960727A EP 01960727 A EP01960727 A EP 01960727A EP 1261599 A1 EP1261599 A1 EP 1261599A1
Authority
EP
European Patent Office
Prior art keywords
diamino
amino
benzene
group
methyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP01960727A
Other languages
German (de)
English (en)
French (fr)
Inventor
Laurent Chassot
Hans-Jürgen BRAUN
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Procter and Gamble Deutschland GmbH
Original Assignee
Wella GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Wella GmbH filed Critical Wella GmbH
Publication of EP1261599A1 publication Critical patent/EP1261599A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/28—Radicals substituted by nitrogen atoms

Definitions

  • the present invention relates to agents for the oxidative dyeing of keratin fibers, in particular human hair, on the basis of a developer substance / coupler substance combination, which contain 1,3-diamino-4-heteroaryl-benzene derivatives as coupler substance, and new 1,3-diamino -4-heteroaryl-benzene derivatives.
  • Oxidation dyes have become very important in the field of coloring keratin fibers, in particular hair coloring.
  • the coloration arises from the reaction of certain developer substances with certain coupler substances in the presence of a suitable oxidizing agent.
  • 2,5-diaminotoluene, 2,5-diaminophenylethyl alcohol, p-aminophenol, 1,4-diaminobenzene and 4,5-diamino-1- (2'-hydroxyethyl) pyrazole are used as developer substances, while resorcinol is used as coupler substances , 2-aminoresorcinol, 1-naphthol, 3-aminophenol, m-phenylenediamine, 2-amino-4- (2'-hydroxy-ethyl) amino-anisole, 1, 3-diamino-4- (2 ' - hydroxyethoxy ) benzene and 2,4-diamino-5-fluorotoluene are mentioned.
  • Oxidation dyes which are used to dye human hair, are subject to numerous additional requirements in addition to dyeing in the desired intensity.
  • the dyes have to be harmless from a toxicological and dermatological point of view and the hair colorations obtained have good lightfastness, perm, fastness to acids and fastness to rubbing. In any case, such stains must remain stable over a period of at least 4 to 6 weeks without exposure to light, friction and chemical agents. It is also necessary that a wide range of different color shades can be produced by combining suitable developer substances and coupler substances.
  • DE-OS 30 28 131 which also describes, among other things, colorants which contain, as coupler substances, special m-phenylenediamines which are substituted in the 4-position by alkyl.
  • the present invention therefore relates to an agent for the oxidative coloring of keratin fibers, such as wool, furs, feathers or hair, in particular human hair, on the basis of a developer substance-coupler substance combination, which as Contains at least one 1,3-diamino-4-heteroaryl-benzene derivative of the formula (I) or its physiologically tolerated salt,
  • X1 is sulfur, oxygen, C-R3 or N-R2;
  • X2 is nitrogen or C-R4;
  • X3 is sulfur, nitrogen, oxygen, CR5 or N-R2;
  • R1, R3, R4 and R5 can be the same or different and independently of one another are hydrogen, a halogen atom (fluorine, chlorine, bromine,
  • Nitro group an amino group, a C ⁇ C ⁇ -monoalkylamino group, a D ⁇ -C -alkylamino group, a di (CC 4 -hydroxyalkyl) -amino group, a C ⁇ C ⁇ -hydroxyalkylamino group, a trifluoromethane group , a -C (O) CH 3 group, a -C (O) CF 3 group, an -Si (CH 3 ) 3 -
  • R2 is hydrogen, a C 1 -C 6 alkyl group, a C 2 -C 4 hydroxyalkyl group, a phenyl group or an acetyl group; where at least one and a maximum of two of the radicals X1 to X3 are the same
  • Preferred compounds of the formula (I) are those in which (i) X1 or X3 is sulfur, X2 is C-R4 and X3 is C-R5 or X1 is C-R3; or (ii) X1 or X3 is sulfur, X2 is C-R4 and X3 is C-R5 or X1 is C-R3, where at least two of the radicals R1, R3, R4 and R5 are hydrogen.
  • 1,3-diamino-4-heteroaryl-benzene derivatives are particularly preferred: 1,3-diamino-4- (thiophene-2-yl) benzene, 1,3-diamino-4- (thiophene-3- yl) -benzene and their physiologically tolerable salts.
  • the compounds of the formula (I) can be used both as free bases and in the form of their physiologically tolerable salts with inorganic or organic acids, such as, for example, hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, propionic acid, lactic acid or citric acid.
  • inorganic or organic acids such as, for example, hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, propionic acid, lactic acid or citric acid.
  • the 1,3-diamino-4-heteroaryl-benzene derivatives of the formula (I) are present in the colorant according to the invention in a total amount of about 0.005 to 20 percent by weight, an amount of about 0.01 to 5 percent by weight and in particular 0.1 1 to 2.5 percent by weight is preferred.
  • developer substances known and suitable for such colorants can be used as developer substances, for example 1,4-diamino-benzene (p-phenylenediamine), 1,4-diamino-2-methyl-benzene (p-toluenediamine), 1,4-diamino-2 , 6-dimethyl-benzene, 1, 4-diamino-3,5-diethyl-benzene, 1, 4-diamino-2,5-dimethyl-benzene, 1, 4-diamino-2,3-dimethyl-benzene, 2 -Chlor-1,4-diaminobenzene, 1,4-diamino-2- (thiophene-2-yl) benzene, 1,4-diamino-2- (thiophene-3-yl) benzene, 1,4-diamino-2 - (pyridin-3-yl) benzene, 2,5-diaminobiphenyl, 1,4-dia
  • the colorant according to the invention may optionally also include other coupler substances, for example 2,6-diamino-pyridine, 2-amino-4 - [((2-hydroxyethyl)) amino] anisole, 2,4-diamino-1-fluoro-5 - methyl-benzene, 2,4-diamino-1-methoxy-5-methyl-benzene, 2,4-diamino-1-ethoxy-5-methyl-benzene, 2,4-diamino-1- (2-hydroxyethoxy) -5-methyl- benzene, 2,4-di [(2-hydroxyethyl) amino] -1, 5-dimethoxy-benzene, 2,3-diamino-6-methoxy-pyridine, 3-amino-6-methoxy-2- (methylamino) - pyridine, 2,6-diamino-3,5-dimethoxy-pyridine, 3,5-diamino-2,6-dimethoxy-pyridine
  • the coupler substances and developer substances can each be contained in the colorant according to the invention individually or in a mixture with one another, the total amount of coupler substances and developer substances in the colorant according to the invention (based on the total amount of the colorant) in each case about 0.005 to 20 percent by weight, preferably about 0.01 to 5.0 percent by weight and in particular 0.1 to 2.5 percent by weight.
  • the total amount of developer-coupler combination contained in the colorant described here is preferably about 0.01 to 20 percent by weight, with an amount of about 0.02 to 10 percent by weight and in particular 0.2 to 6 percent by weight being particularly preferred.
  • the developer substances and coupler substances are generally used in approximately equimolar amounts; however, it is not disadvantageous if the developer substances are present in this respect in a certain excess or deficit (for example in a ratio (coupler: developer) of 1: 2 to 1: 0.5).
  • the colorant according to the invention can additionally contain other color components, for example 6-amino-2-methylphenol and 2-amino-5-methylphenol, and also conventional anionic, cationic, zwitterionic or non-ionic direct dyes, for example Triphenylmethane dyes such as 4 - [(4 , -aminophenyl) - (4 * imino-2 ", 5" - cyclohexadien-1 "-ylidene) -methyl] -2-methylaminobenzene-monohydrochloride (Cl 42 510) and 4 - [(4th 'amino-3'-methylphenyl) - (4 "-imino-3" -methyl-2 ", 5" cyclohexadien-1 "-ylidene) -methyl] -2-methyl-aminobenzene monohydrochloride (Cl 42 520), aromatic nitro dyes such as 4- (2'-hydroxyethyl) amino-nitrotoluene,
  • the coupler substances and developer substances as well as the other color components can also be in the form of the physiologically compatible salts with organic or inorganic acids, such as hydrochloric acid or sulfuric acid, or - if they have aromatic OH groups - in the form of the salts
  • organic or inorganic acids such as hydrochloric acid or sulfuric acid
  • Bases for example as alkali phenolates, are used.
  • the colorant according to the invention is to be used for dyeing hair, it is also possible to use other additives customary for cosmetic compositions, for example antioxidants such as ascorbic acid, thioglycolic acid or sodium sulfite, and perfume oils, Complexing agents, wetting agents, emulsifiers, thickeners and care substances can be included.
  • antioxidants such as ascorbic acid, thioglycolic acid or sodium sulfite
  • perfume oils for example antioxidants such as ascorbic acid, thioglycolic acid or sodium sulfite, and perfume oils, Complexing agents, wetting agents, emulsifiers, thickeners and care substances can be included.
  • the preparation form of the colorant according to the invention can be, for example, a solution, in particular an aqueous or aqueous-alcoholic solution.
  • the particularly preferred preparation forms are a cream, a gel or an emulsion.
  • Their composition represents a mixture of the dye components with the additives customary for such preparations.
  • Usual additives in solutions, creams, emulsions or gels are, for example, solvents such as water, lower aliphatic alcohols, for example ethanol, propanol or isopropanol, glycerol or glycols such as 1,2-propylene glycol, furthermore wetting agents or emulsifiers from the classes of the anionic, cationic, amphoteric or nonionic surfactants such as fatty alcohol sulfates, ethoxylated fatty alcohol sulfates, alkylsulfonates, alkylbenzenesulfonates, alkyltrimethylammonium salts, alkylbetaines, oxyethylated fatty alcohols, oxyethylated nonylphenols, fatty acid alkanolamides and oxyethylated fatty acid ester, also thickeners such as higher fatty alcohols, starch, cellulose derivatives, petrolatum, paraffin oil and fatty acids, and
  • the ingredients mentioned are used in the amounts customary for such purposes, for example the wetting agents and emulsifiers in concentrations of about 0.5 to 30 percent by weight, the thickeners in an amount of about 0.1 to 25 percent by weight and the care substances in a concentration of about 0.1 to 5 weight percent.
  • the colorant according to the invention can react weakly acidic, neutral or alkaline. In particular, it has a pH of 6.5 to 11.5, the basic setting preferably being carried out with ammonia.
  • organic amines for example monoethanolamine and triethanolamine, or else inorganic bases such as sodium hydroxide and potassium hydroxide can also be used.
  • Inorganic or organic acids for example phosphoric acid, acetic acid, citric acid or tartaric acid, are suitable for pH adjustment in the acidic range.
  • the colorant described above is mixed with an oxidizing agent immediately before use, and an amount sufficient for the hair dyeing treatment, depending on the fullness of the hair, generally about 50 to 200 grams, of this mixture is applied to the hair.
  • the ready-to-use oxidation hair dye obtained after mixing with the oxidizing agent preferably has a pH of 6.5 to 11.5.
  • the main oxidizing agents used to develop hair color are hydrogen peroxide or its addition compounds with urea, melamine, sodium borate or sodium carbonate in the form of a 3 to 12 percent, preferably 6 percent, aqueous solution, but also atmospheric oxygen. If a 6 percent hydrogen peroxide solution is used as the oxidizing agent, the weight ratio between hair dye and oxidizing agent is 5: 1 to 1: 2, but preferably 1: 1. Larger amounts of oxidizing agent are used in particular in the case of higher dye concentrations in hair dyeing. medium, or if at the same time more bleaching of the hair is intended.
  • the mixture is allowed to act on the hair at 15 to 50 degrees Celsius for about 10 to 45 minutes, preferably 30 minutes, then the hair is rinsed with water and dried. If necessary, this rinse is washed with a shampoo and possibly rinsed with a weak organic acid, such as citric acid or tartaric acid. The hair is then dried.
  • the colorant according to the invention with a content of 1,3-diamino-4-heteroaryl-benzene derivatives of the formula (I) as a coupler substance enables dyeings with excellent color fastness, in particular with regard to light fastness, wash fastness and rub fastness.
  • the colorant according to the invention offers a wide range of different color nuances depending on the type and composition of the color components, which ranges from blonde to brown, purple, violet to blue and black hues, depending on the developer substance / coupler combination used the intense, stable blue shades that can now be achieved should be emphasized.
  • the very good coloring properties of the colorant according to the present application are further demonstrated by the fact that this means in particular also enables graying, chemically not previously damaged hair to be colored easily and with good coverage.
  • 1,3-diamino-4-heteroaryl-benzene derivatives of the formula (I) according to the invention can be prepared using known Synthesis processes, for example in analogy to the processes described in the exemplary embodiments, take place.
  • the 1, 3-diamino-4-heteroaryl-benzene derivatives of the formula (I) are readily soluble in water and enable dyeings - in particular in the blue color range - with high color intensity and excellent color fastness, in particular as far as light fastness, wash fastness and rub fastness are concerned. They also have excellent storage stability, particularly as a component of the oxidation colorants described here.
  • Another object of the present invention are therefore to provide.
  • reaction mixture is poured into 300 ml of water, a precipitate forming.
  • the precipitate is filtered off and with
  • the mixture is stirred at 80 ° C. for 26 hours and then a mixture of 4.2 g (16.9 mmol) of diboronpinacol ester and 700 mg (0.95 mmol) of PdCl 2 (dppf) is added.
  • the reaction mixture is stirred for a further 14 hours at 80 ° C., then poured onto water and extracted with ethyl acetate.
  • the organic phase is then washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated after filtration.
  • the crude product obtained is purified on deactivated silica gel using hexane / ethyl acetate (1: 1).
  • the reaction mixture is poured into 10 ml of ethyl acetate, the organic phase is extracted with dilute sodium hydroxide solution and then dried with magnesium sulfate.
  • the solvent is distilled off on a rotary evaporator and the residue is purified on silica gel with petroleum ether / ethyl acetate (9: 1).
  • the product thus obtained is heated to 50 ° C. in 4 ml of ethanol.
  • 1.5 ml of a 2.9 molar ethanolic hydrochloric acid solution are added dropwise to produce the hydrochloride.
  • the precipitate is filtered off, washed twice with 1 ml of ethanol and then dried. a.
  • cream-like color carrier compositions are prepared: X g 1, 3-diamino-4-heteroaryl-benzene (coupler substance K1 of the formula (I) according to Table 4) U g developer substance E8 to E15 according to Table 2 Y g coupler substance K11 to K36 according to the table 4 g g direct dye D2 according to Table 3 15.0 g cetyl alcohol 0.3 g ascorbic acid 3.5 g sodium lauryl alcohol diglycol ether sulfate, 28 percent aqueous solution 3.0 g ammonia, 22 percent aqueous solution 0.3 g sodium sulfite, anhydrous ad 100 g water

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP01960727A 2001-02-02 2001-09-10 1,3-diamino-4-heteroaryl-benzol-derivate enthaltende färbemittel für keratinfasern sowie neue 1,3-diamino-4-heteroaryl-benzol-derivate Withdrawn EP1261599A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10104768 2001-02-02
DE10104768 2001-02-02
PCT/EP2001/010411 WO2002062783A1 (de) 2001-02-02 2001-09-10 1,3-diamino-4-heteroaryl-benzol-derivate enthaltende färbemittel für keratinfasern sowie neue 1,3-diamino-4-heteroaryl-benzol-derivate

Publications (1)

Publication Number Publication Date
EP1261599A1 true EP1261599A1 (de) 2002-12-04

Family

ID=7672663

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01960727A Withdrawn EP1261599A1 (de) 2001-02-02 2001-09-10 1,3-diamino-4-heteroaryl-benzol-derivate enthaltende färbemittel für keratinfasern sowie neue 1,3-diamino-4-heteroaryl-benzol-derivate

Country Status (8)

Country Link
US (1) US6811573B2 (pt)
EP (1) EP1261599A1 (pt)
JP (1) JP2004517957A (pt)
AU (1) AU2001282133B2 (pt)
BR (1) BR0109607A (pt)
CA (1) CA2436433A1 (pt)
MX (1) MXPA03006937A (pt)
WO (1) WO2002062783A1 (pt)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10217271A1 (de) * 2002-04-18 2003-11-06 Wella Ag 3-Aminophenol-Derivate und diese Verbindungen enthaltende Färbemittel für Keratinfasern
EP1760072A1 (en) * 2005-08-30 2007-03-07 Wella Aktiengesellschaft 1,3-diaminobenzene derivatives and colorants comprising these compounds
FR3020945B1 (fr) * 2014-05-16 2016-05-06 Oreal Composition pour colorer les fibres keratiniques comprenant une base d'oxydation et un coupleur heteroaryle particulier

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2461494A1 (fr) 1979-07-24 1981-02-06 Oreal Compositions tinctoriales pour cheveux contenant, en tant que coupleur, au moins un diamino-2,4 alkylbenzene
DE3132885A1 (de) * 1981-08-20 1983-03-03 Wella Ag Mittel und verfahren zur faerbung von haaren
US4845291A (en) * 1986-12-24 1989-07-04 Air Products And Chemicals, Inc. Cycloalkenyl aryldiamines
FR2715296B1 (fr) * 1994-01-24 1996-04-12 Oreal Composition de teinture d'oxydation des fibres kératiniques comprenant une paraphénylènediamine, une métalphénylènediamine et un para-aminophénol ou un méta-aminophénol, et procédé de teinture utilisant une telle composition.
DE19812058C1 (de) * 1998-03-19 1999-10-07 Wella Ag Diaminobenzol-Derivate und diese Verbindungen enthaltende Haarfärbemittel

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO02062783A1 *

Also Published As

Publication number Publication date
JP2004517957A (ja) 2004-06-17
AU2001282133B2 (en) 2006-01-05
US20030093867A1 (en) 2003-05-22
CA2436433A1 (en) 2002-08-15
BR0109607A (pt) 2003-02-04
US6811573B2 (en) 2004-11-02
MXPA03006937A (es) 2005-02-17
WO2002062783A1 (de) 2002-08-15

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