US3210252A - 1-methyl-2-hydroxy-4-aminobenzene as a modifier for oxidation dyes - Google Patents

1-methyl-2-hydroxy-4-aminobenzene as a modifier for oxidation dyes Download PDF

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Publication number
US3210252A
US3210252A US240471A US24047162A US3210252A US 3210252 A US3210252 A US 3210252A US 240471 A US240471 A US 240471A US 24047162 A US24047162 A US 24047162A US 3210252 A US3210252 A US 3210252A
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Prior art keywords
methyl
hair
hydroxy
diaminobenzene
benzene
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US240471A
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English (en)
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Blanke Rolf
Gross Erika
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/10Preparations for permanently dyeing the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • A61K8/415Aminophenols
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B22CASTING; POWDER METALLURGY
    • B22DCASTING OF METALS; CASTING OF OTHER SUBSTANCES BY THE SAME PROCESSES OR DEVICES
    • B22D19/00Casting in, on, or around objects which form part of the product
    • B22D19/0009Cylinders, pistons

Definitions

  • the present invention relates to a method and composition for the dyeing of hair and the like, particularly human hair.
  • oxidative dyeing of keratin-containing material can be carried out so as to obtain brilliant colors of high stability, by applying to the material which is to be dyed, such as living hair, a mixture of one or more aromatic p-diamines and/or one or more p-aminophenols, together with 1-methy1-2-hydroxy-4-aminobenzene.
  • Very clear and pure color shades are obtained by applying equimolar amounts of a .p-aminophenol or aromatic p-diamine and of 1-methyl-2-hydroxy-4-aminobenzene.
  • the above described mixture may be applied as an aqueous or alcoholic solution, or dispersed in other suittempted to dye living human hair in this manner, serious 1 ditficulties were encountered due to the fact that the requirements in connection with dyeing living human hair are, of course, much more strict than those pertaining to the dyeing of furs or cut, dead hair.
  • the compositions used for dyeing living hair should be non-toxic and should not cause allergies.
  • the dyed living hair should maintain its color even when subjected to sunlight, moisture, acidic sweat, hair washing compositions and other chemicals used in the care of living hair, for instance hair waving and fixing preparations. It is desired that the developed hair dye on the living hair should be resistant against the above mentioned and other influences so that the desired and initially obtained color will be maintained.
  • the color obtained by dyeing hair with a given composition should be the same regardless of the color of the undyed hair.
  • the dyeing of hair according to the present invention may serve the purpose of giving to the hair the thus obtained color, or to shade thereby the hair color obtained by means of other hair dyeing compositions.
  • the dyeing composition may be applied in any desired consistency, preferably in liquid or cream-like consistency.
  • the dyeing composition may be adjusted so as to react slightly alkaline, neutral or slightly acidic, broadly within a pH range from 2 to 11. In many cases it is particularly advantageous and will result in colors of greater lumi-.
  • the dyeing composition contains 1-methyl-2-hydroxy-4-aminobenzene.
  • any aromatic pdiamine or p-aminophenol may be used.
  • 1,4-diaminobenzene 1,2,4-triaminobenzene 1-methyl-2,5-diaminobenzene l,4-dimethyl-2,5 diaminobenzene l-methoxy-4-chloro-2,S-diaminobenzene 1-methoxy-4-methyl-2,S-diaminobenzene 1-amino-4-hydroxy-benzene 1-amino-2-methyl-4-hydroxy-benzene 1-amino-3 -m ethyl-4-hydroxy-benzene l,3-diamino-4-hydroxy-benzene 4,4-diaminodiphenylamine
  • detergents such as Other objects and advantages of the present invention fatty alcohol sulfonates, alkyl-aryl sulfonates, condensates of fatty alcohol-polyethylene oxide or fatty acid-methyltaurine condensation products; or thickening agents such as
  • Suitable alcohols for forming an alcoholic or aqueous alcoholic solution of the essential components of the dyeing composition include ethanol, isopropanol and polyglycols.
  • additives which may be included in the dyeing composition of the present invention comprise perfume oils, certain essential oils and the like.
  • Example I A solution is formed of:
  • the thus formed solution is mixed with an equal volume of 6% aqueous hydrogen peroxide and applied to the hair for between 20 and 30 minutes at body temperature- Thereafter, the hair is rinsed to remove the excess of the dyeing solution. In this manner a deep violet hair. color is obtained.
  • the thus formed solution is mixed with an equal volume of 6% aqueous hydrogen peroxide, and living hair is treated with the thus formed mixture as described in Example I. A deep blue-violet hair color is obtained.
  • Example 111 A solution is formed of:
  • the thus formed solution is mixed with an equal volume of 6% aqueous hydrogen peroxide, and living hair is treated With the thus formed mixture as described in Example I. A deep, full orange hair color is obtained.
  • Example IV A solution is formed of:
  • the thus formed solution is mixed with an equal volume of 6% aqueous hydrogen peroxide, and living hair is treated with the thus formed mixture as described in Example I. A deep red-violet hair color is obtained.
  • Example V A solution is formed of:
  • the thus formed solution is mixed with an equal volume of 6% aqueous hydrogen peroxide, and living hair is treated with the thus formed mixture as described in Example I. In this manner, beautiful ruby-colored hair is obtained.
  • Example VI A solution is formed of:
  • the thus formed solution is mixed with an equal volume of 6% aqueous hydrogen peroxide, and living hair is treated with the thus formed mixture as described in Example I. A bluish-black hair color is obtained.
  • Acetic acid is added so as to adjust the pH of the solution to 5.
  • the thus formed solution is mixed with an equal volume of 6% aqueous hydrogen peroxide, and living hair is treated with the thus formed mixture as described in Example I. A dark chestnut brown hair color is obtained.
  • Example VIII A solution is formed of:
  • the solution is adjusted to pH 7 (for adjusting the pH of the dyeing solutions, preferably either acetic acid or ammonia solution is used).
  • the thus formed solution is mixed with an equal volume of 6% aqueous hydrogen peroxide, and living hair is treated With the thus formed mixture as described in Example I. A dark mahogany hair color is obtained.
  • Example IX 20 grams 12% potassium oleate solution in 30 grams distilled water, are stirred into 15 grams molten fatty alcohol.
  • a smooth cream is obtained.
  • a solution of the composition described below is stirred into the thus obtained cream:
  • Example X A solution is formed of:
  • a method of dyeing hair comprising the step of applying to hair which is to be dyed 1-methyl-2-hydroxy- 4-aminobenzene, at least one substance selected from the group consisting of 1-methyl-2,S-diaminobenzene, 1,4-diaminobenzene, 1,2,4-triaminobenzene, 1-methyl-2,5-diaminobenzene, 1,4-dimethyl-2,S-diaminobenzene, l-methoxy-4-chloro-2,5-diaminobenzene, 1-methoxy-4-methyl- 2,5-diaminobenzene, l-amino 4 hydroxy benzene, 1 amino-2-methyl-4-hydroxy-benzene, 1-amino-3-methyl-4- hydroxy-benzene, 1,3-diamino-4-hydroxy-benzene and 4,4-diaminodiphenylamine, and an effective amount of an oxidizing agent therefor.
  • a method of dying hair comprising the step of applying to hair which is to be dyed substantially equimolar quantities of 1-methy1-2-hydroxy-4-aminobenzene, and of at least one substance selected from the group consisting of 1-methyl-2,5-diaminobenzene, 1,4-diaminobenzene, 1,2,4-triaminobenzene, 1-methyl-2,5-diamino benzene, 1,4-dimethyl-2,S-diaminobenzene, 1-methoxy-4- chlor0-2,5-diaminobenzene, 1-methoxy-4-methyl-2,5-di aminobenzene, 1-amino-4-hydroxy-benzene, 1-amino-2- methyl-4-hydroxy-benzene, 1-amino-3-methyl-4-hydroxybenzene, 1,3-diamino-4-hydroxy-benzene, and 4,4-diaminodiphenylamine, and an effective amount of hydrogen peroxide as an oxid
  • a method of dyeing hair comprising the step of applying to hair which is to be dyed 1-methyl-2-hydroxy- 4-aminobenzene, at least one aromatic p-diamine adapted to form a hair dye upon oxidation, and an effective amount of oxidizing agent therefor.
  • a method of dyeing hair comprising the step of applying to hair which is to be dyed I-methyl-Z-hydroxy- 44aminobenzene, :at least one p-aminop'henol adapted to form a hair dye upon oxidation, and an effective amount of oxidizing agent therefor.
  • a method of dyeing hair comprising the step of applying to hair which is to be dyed a carrier substance compatible With hair and having distributed therethrough substantially equimolar quantities of 1 methyl 2 hydroxy- 4 aminobenzene, and of at least one substance selected from the group consisting of 1 methyl 2,5 diaminobenzene, 1,4 diaminobenzene, 1,2,4 triaminobenzene, 1 methyl 2,5 diaminobenzene, 1,4 dimethyl 2,5- diaminobenzene, 1 methoxy 4 chloro 2,5 diaminobenzene, 1 methoxy 4 methyl 2,5 diaminobenzene, 1 amino 4 hydroxy benzene, 1 amino 2 methyl- 4 hydroxy benzene, 1 amino 3 methyl 4 hydroxy benzene, 1,3 diamino 4 hydroxy benzene and 4,4-diaminodiphenylamine, and an effective amount of hydrogen peroxide as an oxidizing agent therefor.
  • a composition of matter for dyeing of hair which comprises 1 methyl 2 hydroxy 4 aminobenzene, at least one substance selected from the group consisting of 1 methyl 2,5 diaminobenzene, 1,4 diaminobenzene, 1,2,4 triaminobenzene, 1 methyl -2,5 diaminobenzene, 1,4 dimethyl 2,5 diaminobenzene, 1 methoxy 4- chloro 2,5 diaminobenzene, 1 methoxy- 4 methyl- 2, 5 diaminobenzene, 1 amino 4 hydroxy benzene, 1 amino 2 methyl 4 hydroxy benzene, 1 amino- 3 methyl 4 hydroxy benzene, 1,3 diamino 4- hydroxy benzene, and 4,4 diaminodiphenylamine, and an effective amount of an oxidizing agent therefor.
  • a composition of matter for dyeing of hair which comprises substantially equimolar quantities of 1 methyl- 2 hydroxy 4 aminobenzene and of at least one substance selected from the group consisting of 1 methyl- 2,5 diaminobenzene, 1,4 diaminobenzene, 1,2,4 triaminobenzene, 1 methyl 2,5 diaminobenzene, 1,4- dimethyl 2,5 diaminobenzene, 1 methoxy 4 chloro- 2,5 diaminobenzene, 1 methoxy 4 methyl 2,5 diamino benzene, 1 amino 4 hydroxy benzene, 1- amino 2 methyl 4 hydroxy benzene, 1 amino 3- methyl 4 hydroxy benzene, 1,3 diamino 4 hydroxy benzene, and 4,4-diaminodiphenylamine, and an eifective amount of hydrogen peroxide as an oxidizing agent therefor.
  • composition of matter for dyeing of hair which comprises 1-methyl-2-hydroxy-4-aminobenzene, at least one aromatic p-diamine adapted to form a hair dye upon oxidation, and an effective amount of an oxidizing agent therefor.
  • a composition of matter for dyeing of hair which comprises 1-methyl-2-hydroxy-4-aminobenzene, at least one p-aminophenol adapted to form a hair dye upon oxidation, and an effective amount of an oxidizing agent therefor.
  • a composition of matter for dyeing of hair which comprises a carrier substance compatible With hair and having distributed therethrough substantially equimolar quantities of 1-methyl-2-hydroxy-4-aminobenzene and of at least one substance selected from the group consisting of 1-methyl-2,S-diaminobenzene, 1,4-diaminobenzene, 1, 2,4 triaminobenzene, 1 methyl 2,5 diaminobenzene, 1,4-dimethyl 2,5 diaminobenzene, 1 methoxy 4- chloro 2,5 diaminobenzene, 1 methoxy 4 methyl- 2, 5 diaminobenzene, 1 amino 4 hydroxy benzene, 1 amino 2 methyl 4 hydroxy benzene, 1 amino- 3 methyl 4 hydroxy benzene, 1,3 diamino 4 hydroxy-benzene and 4,4-diaminodiphenylamine, and an effective amount of hydrogen peroxide as an oxidizing agent therefor.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Cosmetics (AREA)
US240471A 1961-11-22 1962-11-23 1-methyl-2-hydroxy-4-aminobenzene as a modifier for oxidation dyes Expired - Lifetime US3210252A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DESCH30596A DE1143605B (de) 1961-11-22 1961-11-22 Mittel zum Faerben von lebenden Haaren

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BE (1) BE625116A (fi)
DE (1) DE1143605B (fi)
GB (1) GB973599A (fi)

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3413073A (en) * 1965-04-21 1968-11-26 Oreal Substituted paradiamino-anisole and its use for dyeing human hair and keratinic fibers
US3867094A (en) * 1970-12-30 1975-02-18 Oreal Dyeing keratinous fibers with dye compositions containing indoanilines
US3876368A (en) * 1970-09-18 1975-04-08 Oreal Indamines for dyeing keratinic fibers
US3884627A (en) * 1971-10-04 1975-05-20 Clairol Inc Oxidative hair dye compositions
US3898032A (en) * 1971-06-11 1975-08-05 Zotos Int Inc Oxidative hair-coloring mixtures containing a conditioning agent
US3899288A (en) * 1971-12-02 1975-08-12 Jean Galerne Keratinic fibres oxidation dyeing compositions containing a carbonate of an alkali metal amino acid
US3905761A (en) * 1969-08-11 1975-09-16 Oreal Composition and method for dyeing keratinous fibers
US3918896A (en) * 1973-06-22 1975-11-11 Oreal Dye composition for keratinic fibers containing an oxidation base and a meta-aminophenol coupler
US3929403A (en) * 1969-06-11 1975-12-30 Oreal Process for producing indoanilines and keratin fiber dye composition containing the same
US3931912A (en) * 1971-08-12 1976-01-13 The Gillette Company Two-part hair dye or hair bleach package
US3957424A (en) * 1971-10-27 1976-05-18 The Procter & Gamble Company Enzyme-activated oxidative process for coloring hair
US3970423A (en) * 1971-10-04 1976-07-20 Clairol Incorporated Oxidative hair dye compositions
US3981677A (en) * 1974-01-02 1976-09-21 Clairol Incorporated Oxidative hair dye compositions containing N-substituted o-phenylenediamines and method for their use
US4045170A (en) * 1970-12-30 1977-08-30 L'oreal Hair dye composition containing an indoaniline
US4065255A (en) * 1975-06-26 1977-12-27 L'oreal 2-Methyl-5-N-hydroxyalkylaminophenol in an oxidation dye composition and method of using the same
US4171203A (en) * 1976-06-28 1979-10-16 Henkel Kommanditgesellschaft Auf Aktien Hair dye compositions containing 3,5-diamino-2-substituted-alkylbenzenes
US5073173A (en) * 1990-05-18 1991-12-17 Clairol Incorporated Dye couplers
US5183941A (en) * 1989-05-18 1993-02-02 Clairol Incorporated Hair dye coupler compounds
EP0630642A1 (en) 1993-05-17 1994-12-28 Bristol-Myers Company Naphthol couplers
JPH0834716A (ja) * 1994-01-24 1996-02-06 L'oreal Sa パラ−フェニレンジアミン誘導体および2−メチル−5−アミノフェノールを含有する、ケラチン繊維の酸化染色用組成物、および該組成物を用いる染色方法
US5514188A (en) * 1993-07-13 1996-05-07 L'oreal Oxidation dye composition for keratinous fibres comprising a para-aminophenol, 2-methyl-5-aminophenol and a para-phenylenediamine and/or a bis(phenylalkylenediamine)
US5693101A (en) * 1993-12-22 1997-12-02 L'oreal Composition for the oxidation dyeing of keratinous fibres comprising a 3-fluoropara-aminophenol and at least one coupler selected from a meta-aminophenol and a meta-phenylenediamine and dyeing process using such a composition
US5899212A (en) * 1998-05-07 1999-05-04 Novo Nordisk A/S Re-formation of keratinous fibre cross links
US5961666A (en) * 1997-11-19 1999-10-05 Lim; Mu-Ill Hair dye compositions containing 3-substituted-4-aminophenols and 2-substituted-1-naphthols
WO2014131579A1 (de) * 2013-02-27 2014-09-04 Henkel Ag & Co. Kgaa Multitonale einschritt-färbungen i

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2833989A1 (de) * 1978-08-03 1980-02-21 Wella Ag Mittel zum faerben von haaren
FR2706297B1 (fr) * 1993-06-16 1995-08-18 Oreal Composition de teinture d'oxydation des fibres kératiniques comprenant un paraaminophénol, un méta-aminophénol et un ortho-aminophénol, et procédé de teinture utilisant une telle composition.

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB805746A (en) * 1955-11-18 1958-12-10 Oreal Improvements in or relating to the dyeing of animal fibres

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB805746A (en) * 1955-11-18 1958-12-10 Oreal Improvements in or relating to the dyeing of animal fibres

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3413073A (en) * 1965-04-21 1968-11-26 Oreal Substituted paradiamino-anisole and its use for dyeing human hair and keratinic fibers
US3929403A (en) * 1969-06-11 1975-12-30 Oreal Process for producing indoanilines and keratin fiber dye composition containing the same
US3905761A (en) * 1969-08-11 1975-09-16 Oreal Composition and method for dyeing keratinous fibers
US3876368A (en) * 1970-09-18 1975-04-08 Oreal Indamines for dyeing keratinic fibers
US3867094A (en) * 1970-12-30 1975-02-18 Oreal Dyeing keratinous fibers with dye compositions containing indoanilines
US4045170A (en) * 1970-12-30 1977-08-30 L'oreal Hair dye composition containing an indoaniline
US3898032A (en) * 1971-06-11 1975-08-05 Zotos Int Inc Oxidative hair-coloring mixtures containing a conditioning agent
US3931912A (en) * 1971-08-12 1976-01-13 The Gillette Company Two-part hair dye or hair bleach package
US3970423A (en) * 1971-10-04 1976-07-20 Clairol Incorporated Oxidative hair dye compositions
US3884627A (en) * 1971-10-04 1975-05-20 Clairol Inc Oxidative hair dye compositions
US3957424A (en) * 1971-10-27 1976-05-18 The Procter & Gamble Company Enzyme-activated oxidative process for coloring hair
US3899288A (en) * 1971-12-02 1975-08-12 Jean Galerne Keratinic fibres oxidation dyeing compositions containing a carbonate of an alkali metal amino acid
US3918896A (en) * 1973-06-22 1975-11-11 Oreal Dye composition for keratinic fibers containing an oxidation base and a meta-aminophenol coupler
US3981677A (en) * 1974-01-02 1976-09-21 Clairol Incorporated Oxidative hair dye compositions containing N-substituted o-phenylenediamines and method for their use
US4065255A (en) * 1975-06-26 1977-12-27 L'oreal 2-Methyl-5-N-hydroxyalkylaminophenol in an oxidation dye composition and method of using the same
US4171203A (en) * 1976-06-28 1979-10-16 Henkel Kommanditgesellschaft Auf Aktien Hair dye compositions containing 3,5-diamino-2-substituted-alkylbenzenes
US5183941A (en) * 1989-05-18 1993-02-02 Clairol Incorporated Hair dye coupler compounds
US5073173A (en) * 1990-05-18 1991-12-17 Clairol Incorporated Dye couplers
EP0630642A1 (en) 1993-05-17 1994-12-28 Bristol-Myers Company Naphthol couplers
US5514188A (en) * 1993-07-13 1996-05-07 L'oreal Oxidation dye composition for keratinous fibres comprising a para-aminophenol, 2-methyl-5-aminophenol and a para-phenylenediamine and/or a bis(phenylalkylenediamine)
US5693101A (en) * 1993-12-22 1997-12-02 L'oreal Composition for the oxidation dyeing of keratinous fibres comprising a 3-fluoropara-aminophenol and at least one coupler selected from a meta-aminophenol and a meta-phenylenediamine and dyeing process using such a composition
JPH0834716A (ja) * 1994-01-24 1996-02-06 L'oreal Sa パラ−フェニレンジアミン誘導体および2−メチル−5−アミノフェノールを含有する、ケラチン繊維の酸化染色用組成物、および該組成物を用いる染色方法
US5961666A (en) * 1997-11-19 1999-10-05 Lim; Mu-Ill Hair dye compositions containing 3-substituted-4-aminophenols and 2-substituted-1-naphthols
US5899212A (en) * 1998-05-07 1999-05-04 Novo Nordisk A/S Re-formation of keratinous fibre cross links
WO2014131579A1 (de) * 2013-02-27 2014-09-04 Henkel Ag & Co. Kgaa Multitonale einschritt-färbungen i
US9402795B2 (en) 2013-02-27 2016-08-02 Henkel Ag & Co. Kgaa Multi-tonal one-step dyes

Also Published As

Publication number Publication date
BE625116A (fi)
GB973599A (en) 1964-10-28
DE1143605B (de) 1963-02-14

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