US3011858A - Process for dyeing hair, fur and other keratinic fibers with dihydroxyaminobenzenes - Google Patents

Process for dyeing hair, fur and other keratinic fibers with dihydroxyaminobenzenes Download PDF

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US3011858A
US3011858A US805136A US80513659A US3011858A US 3011858 A US3011858 A US 3011858A US 805136 A US805136 A US 805136A US 80513659 A US80513659 A US 80513659A US 3011858 A US3011858 A US 3011858A
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solution
dihydroxyaminobenzene
hair
shade
value
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US805136A
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Lantz Robert
Kalopissis Gregoire
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LOreal SA
Monsavon LOreal SA
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LOreal SA
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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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/415—Aminophenols
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/30—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts
    • D06P3/305—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts with oxidation dyes

Definitions

  • This invention relates to a process for dyeing hair, fur and other keratinic fibers, and particularly live human hair.
  • a process for the dyeing of hair, fur and other keratinic fibers comprises impregnating the said fibers with a composition comprising in aqueous solution at least one dihydroxyaminobenzene selected from 2,5-dihydroxyaminobenzene (aminohydroquinone), 2,4-dihydroxyaminobenzene (aminoresorcinol), and 3,4-dihydroxyaminobenzene (aminopyrocatechol) and the acid addition salts thereof, and subjecting the impregnated fibers to the action of an oxidizing agent (which may be the oxygen of the air).
  • an oxidizing agent which may be the oxygen of the air
  • the process is particularly valuable for dyeing live human hair.
  • the hydroxyaminobenzenes of the invention individually or in mixture, it gives natural shades suitable for this use, which range from blond to light brown and black.
  • the hair while in contact with the air, is impregnated with an aqueous solution of one or more of the aforesaid hydroxyaminobenzenes.
  • the results are particularly favourable when the pH-value of this solution is adjusted between 2 and 10 and preferably between 6 and 8.5.
  • the foregoing procedure may also be applied to furs and other keratinous substances.
  • the process is carried out in two steps, one in which hydroxyaminobenzene is fixed on the fiber to be dyed, while in the other one the oxidation is efiected.
  • the fixing of the aminohydroxyl derivative is advantageously effected in an aqueous medium of which the pH is lower than 9.
  • oxidation may be effected by the air after the fiber has been impregnated, with an alkaline solution of a pH-value higher than 7. This oxidation can be accelerated by the use of another oxidizing agent such as hydrogen peroxide.
  • aqueous dyeing compositions for use in the aforesaid process, more especially for dyeing live human hair, said compositions consisting essentially of an aqueous solution of at least one dihydroxyaminobenzene selected from 2,5'-dihydroxyaminobeuzene (aminohydroquinone) 2,4-dihydroxyaminobenzene (aminoresorcinol) and 3,4-dihydroxyaminobenzene (aminopyrocatechol) and the acid addition salts thereof, the pH-value of said solution being comprised between 2 and 10 and preferably between 6 and 8.5.
  • dihydroxyaminobenzene selected from 2,5'-dihydroxyaminobeuzene (aminohydroquinone) 2,4-dihydroxyaminobenzene (aminoresorcinol) and 3,4-dihydroxyaminobenzene (aminopyrocatechol) and the acid addition salts thereof, the pH-value of said solution being comprised between 2 and 10
  • the dyeing process of the invention permits of readily obtaining all the shades intermediate between those given individually by the specified dihydroxyaminobenzenes. These intermediate shades can be obtained by employing variable proportions of these derivatives in one and the same composition. it is therefore possible to prepare,
  • the pH-value of the solution obtained is about 9.
  • This solution is applied to grey hair and is allowed to act thereon for 20 minutes in contact with the air. After rinsing and drying, the hair is dyed in a golden blond shade.
  • Example 11 A solution is prepared by mixing:
  • Example 111 A solution is prepared by mixing:
  • the pH-value of the solution thus prepared is about 7. If this solution is applied for about 20 minutes to grey hair, there is obtained after rinsing and drying a golden blond shade which does not change in the course of time.
  • Example IV A solution is prepared by mixing:
  • Example V A solution prepared from:
  • Ammonium alkylsulfate (alkyl being taken as the average chain length of mixed fatty alcohols derived from coconut-oil) with a 20% content in free unreacted fatty alcohols l 2 N sodium carbonate solution in a quantity sufiicient to obtain a pH-value of 7.
  • Example VII (pH about 2.3), there is obtained under the same conditions a golden chestnut shade.
  • Example IX By replacing the 3,4-dihydroxyaminobenzene hydrochloride solution of Example VII by a 3% by weight aqueous solution of 2,4-dihydroxyaminobenzene hydrochloride (pH about 2.5) there is obtained, under the same conditions, a dull blond shade.
  • Example X A solution having the following composition is prepared:
  • the pH-value of the solution obtained is about 8. This solution is applied for 20 minutes to grey hair and a grey shade tinged with gold is obtained.
  • Example XI There is prepared a solution containing:
  • Example XII There is prepared a solution containing:
  • Example XIV There is prepared a solution containing:
  • This mixture is applied for 20 minutes to grey hair (containing 85-90% of white hair), whereby there is obtained, after rinsing and drying, a golden-chestnut shade.
  • Example XV There is prepared a solution containing:
  • Example XVI The procedure of Example XV is followed, the 2,5-dihydroaminobenzene hydrobromide being replaced by 2,4- dihydroxyarninobenzene hydrochloride in a quantity of 6 g. A stable black shade is obtained.
  • Example XVII There is prepared a solution containing:
  • the pH-value of the solution obtained is about 5.
  • Grey hair is impregnated with this solution and, after contact for 20 minutes, the hair is rinsed. A 1.2% hydrogen peroxide solution is thereafter applied for, 10 minutes and the hair is again rinsed. There is thus obtained a stable mahogany shade.
  • Example XVIII A solution is prepared as in Example XViI, but the 3,4-dihydroxyarninobenzene hydrochloride is replaced by 2,5-dihydroxyaminobenzene hydrobromide in a quantity of 3.8 g.
  • Example XIX A solution is prepared under the same conditions as in Example XVII but the 3,4-dihydroxyaminobenzene hydrochloride is replaced by 2,4-dihydroxyaminobenzene hydrochloride in a quantity of 3 g.
  • Example XVII After treatment under the same conditions as in Example XVII, a dark ash-blond shade is obtained.
  • Example XX A piece of unmord'anted rabbit skin is introduced into (b) Mordanted with chromium, there is obtained a brownish-black shade.
  • Example XXI Under the same conditions as in Example XX, but replacing the 2,4-dihydroxyaminobenzene hydrochloride by an equivalent quantity of 2,4-dihydroxyaminobenzene hydrobromide, a brown shade is obtained on an unmordanted rabbit skin, and a dark brown shade is obtained on a rabbit skin mordanted with copper.
  • the process according to the invention also comprises, in a first step, the application of the dyeing composition and the impregnation of the hair for a period of about 20 minutes and in a second step after rinsing of the hair, the impregnation of the hair by means of a hydrogen peroxide solution for a period of the order of 10 minutes (Examples XVII to XIX).
  • the dyeing process according to the invention may comprise other forms of application within the ability of the. person skilled in the art, in the light of the present description.
  • any appropriate oxidizing agent already used with oxidation dyes may be employed.
  • agents of the type usually employed in hair dyeing e.g. reducing, thickening and foaming agents for the purpose 'of facilitating their preservation, their application and their penetration into the fiber.
  • a process for dyeing live human hair and other keratinous fibers which process comprises impregnating said fibers with an aqueous solution of at least one dihydroxyaminobenzene selected from the group consisting of 2.5 dihydroxyaminobenzene, 2.4 dihydroxyaminobenzene, 3.4 dihydroxyaminobenzene and acid addition' salts thereof, said solution being brought to a pH between 2 and 10 by addition of a base chosen from the group consisting of sodium carbonate, sodium bicarbonate and sodium acetate, the keratinous fibers being thereafter subjected to the action of an oxidizing agent.

Description

PRQCESS FOR DYEING HAIR, FUR AND OTHER KERATINIC FIBERS WITH DIHYDRGXYAMIYG- BENZENES Robert Lantz and Gregoire Kalopissis, Paris, France, assignors to Societe Anonyme dite: Societe MonsavonlOreal, Paris, France, a corporation of France No Drawing. Filed Apr. 9, 1959, Ser. No. 805,136
Claims priority, application France Apr. 15, 1958 7 Claims. (Cl. 811) This invention relates to a process for dyeing hair, fur and other keratinic fibers, and particularly live human hair.
According to the present invention a process for the dyeing of hair, fur and other keratinic fibers comprises impregnating the said fibers with a composition comprising in aqueous solution at least one dihydroxyaminobenzene selected from 2,5-dihydroxyaminobenzene (aminohydroquinone), 2,4-dihydroxyaminobenzene (aminoresorcinol), and 3,4-dihydroxyaminobenzene (aminopyrocatechol) and the acid addition salts thereof, and subjecting the impregnated fibers to the action of an oxidizing agent (which may be the oxygen of the air).
The process is particularly valuable for dyeing live human hair. By the use of the hydroxyaminobenzenes of the invention, individually or in mixture, it gives natural shades suitable for this use, which range from blond to light brown and black.
According to one method of carrying out the process of the invention the hair, while in contact with the air, is impregnated with an aqueous solution of one or more of the aforesaid hydroxyaminobenzenes. The results are particularly favourable when the pH-value of this solution is adjusted between 2 and 10 and preferably between 6 and 8.5. The foregoing procedure may also be applied to furs and other keratinous substances.
According to another method of carrying out the process of the invention the process is carried out in two steps, one in which hydroxyaminobenzene is fixed on the fiber to be dyed, while in the other one the oxidation is efiected. The fixing of the aminohydroxyl derivative is advantageously effected in an aqueous medium of which the pH is lower than 9. If desired oxidation may be effected by the air after the fiber has been impregnated, with an alkaline solution of a pH-value higher than 7. This oxidation can be accelerated by the use of another oxidizing agent such as hydrogen peroxide. it is also possible to add hydrogen peroxide directly to the solution containing the 'hydroxyaminobenzene at the time of its application to the fiber, in accordance with the conventional technique employed with oxidation dyes, this procedure obviating the second step.
According to a further feature of the invention there are provided aqueous dyeing compositions for use in the aforesaid process, more especially for dyeing live human hair, said compositions consisting essentially of an aqueous solution of at least one dihydroxyaminobenzene selected from 2,5'-dihydroxyaminobeuzene (aminohydroquinone) 2,4-dihydroxyaminobenzene (aminoresorcinol) and 3,4-dihydroxyaminobenzene (aminopyrocatechol) and the acid addition salts thereof, the pH-value of said solution being comprised between 2 and 10 and preferably between 6 and 8.5.
The dyeing process of the invention permits of readily obtaining all the shades intermediate between those given individually by the specified dihydroxyaminobenzenes. These intermediate shades can be obtained by employing variable proportions of these derivatives in one and the same composition. it is therefore possible to prepare,
States Patent Example I A solution is prepared by mixing:
G. 2,5-dihydroxyaminobenzene hydrobromide 3.8 Sodium carbonate 3.1
Water to make cc.
The pH-value of the solution obtained is about 9.
This solution is applied to grey hair and is allowed to act thereon for 20 minutes in contact with the air. After rinsing and drying, the hair is dyed in a golden blond shade.
Example 11 A solution is prepared by mixing:
G. 2,4-dihydroxyaminobenzene hydrochloride 3 Sodium carbonate 3 Water to make 100 cc.
By applying this solution (having a pH-value of about 9) as in the foregoing example to grey hair, there is obtained after rinsing and drying a brown shade.
Example 111 A solution is prepared by mixing:
G. 2,S-dihydroxyaminobenzene hydrobromide 3.80 Sodium bicarbonate 43 Water to make 100 cc.
The pH-value of the solution thus prepared is about 7. If this solution is applied for about 20 minutes to grey hair, there is obtained after rinsing and drying a golden blond shade which does not change in the course of time.
Example IV A solution is prepared by mixing:
G. 2,4-dihydroxyaminobenzene hydrochloride 3 Sodium bicarbonate 4.4
Water to make 100 cc.
This solution has a pH-value of about 7 and applied as in Example III it gives a very stable blue-black shade.
Example V A solution prepared from:
2,5-dihydroxyaminobenzene hydrobromide 4.8
Ammonium alkylsulfate (alkyl being taken as the average chain length of mixed fatty alcohols derived from coconut-oil) with a 20% content in free unreacted fatty alcohols l 2 N sodium carbonate solution in a quantity sufiicient to obtain a pH-value of 7.
Water to make 100 cc.
Applied as in Example III this solution gives a golden blond shade on grey hair.
xample VI In the same manner as in the preceding examples, a blue-black shade is obtained by applying to grey hair a solution having the following composition:
2,4-dihydroxyaminobenzene hydrochloride 6.46 Ammonium alkylsulfate (alkyl being taken as the average chain length of mixed fatty alcohols derived from coconut-oil) with a 20% content in free, unreacted fatty alcohols 0.8
2 N sodiumcarbonate solution, in a quantity suffi- V cient to obtain a pH-value of 7. Water to make 100 cc.
Example VII (pH about 2.3), there is obtained under the same conditions a golden chestnut shade.
Example IX By replacing the 3,4-dihydroxyaminobenzene hydrochloride solution of Example VII by a 3% by weight aqueous solution of 2,4-dihydroxyaminobenzene hydrochloride (pH about 2.5) there is obtained, under the same conditions, a dull blond shade.
Example X A solution having the following composition is prepared:
V I G. 2,4-dihydroxyaminobenzene hydrochloride 1.5 2,5-dihydroxyaminobenzene hydrobromide 1.9 Sodium carbonate 2 Water to make 100 cc.
The pH-value of the solution obtained is about 8. This solution is applied for 20 minutes to grey hair and a grey shade tinged with gold is obtained.
Example XI There is prepared a solution containing:
. G. 3,4-dihydroxyaminobenzene hydrochloride 3 2,5-dihydroxyaminobenzene hydrobromide 2.4
2 N sodium carbonate solution in a quantity sufficient to obtain a pH-value of about 7. Water to make 100 cc. 7
This solution is applied for 20 minutes to grey hair (containing 85-90% of white hair). There is thus obtained, after rinsing and drying of the hair, a light chestnut shade. 1
Example XII There is prepared a solution containing:
. G. 3,4-dihydroxyaminobenzene hydrochloride 1.6 2,5-dihydroxyaininobenzene hydrobromide 2 2 N sodium carbonate solution in a quantity sufficient to obtain a pI-I-value of 7. Water to make 100 cc.
By proceeding as in Example XI, a blond shade is obtained after rinsing and drying.
4 Example XIII The following solution is prepared:
3,4-dihydroxyaminobenzene hydrochloride 6.4 2,S-dihydroxyaminobenzene hydrobromide 8 Sodium carbonate in a quantity sufficient to obtain a pH-value of 7. Water to make 100* cc.
By proceeding as in Example XI and rinsing and drying, a dark brown shade is obtained.
Example XIV There is prepared a solution containing:
G. 3,4-dihydroxyaminobenzene hydrochloride 3.23 2,S-dihydroxyaminobenzene hydrobrornide 4.12 2 N sodiumwcarbonate solution in a quantity sufiicient to obtain a pH-value of 7. Sulphate of fatty alcohols of copra (ammonium salt of) containing 20% of fatty alcohols 0.7
Water to make 100 cc.
This mixture is applied for 20 minutes to grey hair (containing 85-90% of white hair), whereby there is obtained, after rinsing and drying, a golden-chestnut shade.
Example XV There is prepared a solution containing:
. G. 2,S-dihydroxyaminobenzene hydrobromide 7.6 Sodium hydrogen carbonate 9.6
Water to make 100 cc.
This solution, with an addition of an equal quantity of a 0.6% solution of hydrogen peroxide is immediately applied to grey hair. After contact for 20 minutes, a golden blond shade is obtained.
Example XVI The procedure of Example XV is followed, the 2,5-dihydroaminobenzene hydrobromide being replaced by 2,4- dihydroxyarninobenzene hydrochloride in a quantity of 6 g. A stable black shade is obtained.
Example XVII There is prepared a solution containing:
G. 3,4-dihydroxyaminobenzene hydrochloride 3.0 Sodium acetate (cryst.) NaOOC-CH ,3H O 2.5
Water to make 100 cc.
The pH-value of the solution obtained is about 5.
Grey hair is impregnated with this solution and, after contact for 20 minutes, the hair is rinsed. A 1.2% hydrogen peroxide solution is thereafter applied for, 10 minutes and the hair is again rinsed. There is thus obtained a stable mahogany shade.
Example XVIII A solution is prepared as in Example XViI, but the 3,4-dihydroxyarninobenzene hydrochloride is replaced by 2,5-dihydroxyaminobenzene hydrobromide in a quantity of 3.8 g.
7 By proceeding under the same conditions as in Example XVII, a light chestnut shade is obtained.
Example XIX A solution is prepared under the same conditions as in Example XVII but the 3,4-dihydroxyaminobenzene hydrochloride is replaced by 2,4-dihydroxyaminobenzene hydrochloride in a quantity of 3 g.
.After treatment under the same conditions as in Example XVII, a dark ash-blond shade is obtained.
Example XX A piece of unmord'anted rabbit skin is introduced into (b) Mordanted with chromium, there is obtained a brownish-black shade.
(c) Mordanted with iron, there is obtained shade.
a brown Example XXI Under the same conditions as in Example XX, but replacing the 2,4-dihydroxyaminobenzene hydrochloride by an equivalent quantity of 2,4-dihydroxyaminobenzene hydrobromide, a brown shade is obtained on an unmordanted rabbit skin, and a dark brown shade is obtained on a rabbit skin mordanted with copper.
The foregoing examples illustrate that it is possible to use a dyeing composition according to the invention which contains either a single dihydroxyaminobenzene compound (Examples I and II, solution having a pH- value of about 9; Examples III to VI, solution having a pH-value of about 7; Examples VII to IX, solution having a pH-value in the neighbourhood of 2.5; and Examples XV to XVIII), or two dihydroxyaminobenzene compounds (Examples X to XIV). It is also possible in accordance with the invention to apply to hair an aqueous composition with which there has been previously mixed an oxidizing agent such as a hydrogen peroxide solution (Examples XV and XVI). Finally, the process according to the invention also comprises, in a first step, the application of the dyeing composition and the impregnation of the hair for a period of about 20 minutes and in a second step after rinsing of the hair, the impregnation of the hair by means of a hydrogen peroxide solution for a period of the order of 10 minutes (Examples XVII to XIX).
It will be understood that the dyeing process according to the invention may comprise other forms of application within the ability of the. person skilled in the art, in the light of the present description. Thus, any appropriate oxidizing agent already used with oxidation dyes may be employed. It is also possible to add to the dyeing solution according to the invention agents of the type usually employed in hair dyeing, e.g. reducing, thickening and foaming agents for the purpose 'of facilitating their preservation, their application and their penetration into the fiber.
What we claim is:
. l. A process for dyeing live human hair and other keratinous fibers which process comprises impregnating said fibers with an aqueous solution of at least one dihydroxyaminobenzene selected from the group consisting of 2.5 dihydroxyaminobenzene, 2.4 dihydroxyaminobenzene, 3.4 dihydroxyaminobenzene and acid addition' salts thereof, said solution being brought to a pH between 2 and 10 by addition of a base chosen from the group consisting of sodium carbonate, sodium bicarbonate and sodium acetate, the keratinous fibers being thereafter subjected to the action of an oxidizing agent.
2. A process according to claim 1 wherein the impregnating solution contains two of the said dihydroxyaminobenzenes.
3. A process according to claim 1 wherein the impregnating solution has a pH value between 6 and 8.5.
4. A process according to claim 1 wherein the oxidation is effected by ambient air.
5. A process according to claim 1 wherein the oxidizing agent is a diluted hydrogen peroxide solution.
6. A process according to claim 5, where n the hydro-- gen peroxide is included in the impregnating solution.
7. A process according to claim 1, wherein the hair is first treated with a mordanting solution.
References Cited in the file of this patent Heilingotter: Am. Perf. and Ess. Oil 1Review, May 1954, pp. 345-348.
Eggers et al.: Chem. Abs, :6982d (1956).
Chem. Abst., 47:9191-9193 (1953).
Sagarin: Cosmetics, Science and Technology, Interscience PubL, Inc., N.Y. (1957), pp. 5034.

Claims (1)

1. A PROCESS FOR DYEING LIVE HUMAN HAIR AND OTHER KERATINOUS FIBERS WHICH PROCESS COMPRISES IMPREGNATING SAID FIBERS WITH AN AQUEOUS SOLUTION OF AT LEAST ONE DIHYDROXYAMINOBENZENE SELECTED FROM THE GROUP CONSISTING OF 2.5 DIHYDROXYAMOBENZENE, 2,4 DIHYDROXYAMINOBENZENE, 3.4 DIHYDROXYAMINOBENZENE AND ACID ADDITION SALTS THEREOF, SAID SOLUTION BEING BROUGHT TO A PH BETWEEN 2 AND 10 BY ADDITION OF A BASE CHOSEN FROM THE GROUP CONSISTING OF SODIUM CARBONATE, SODIUM BICARBONATE AND SODIUM ACETATE, THE KERATINOUS FIBERS BEING THEREAFTER SUBJECTED TO THE ACTION OF AN OXIDIZING AGENT.
US805136A 1958-04-15 1959-04-09 Process for dyeing hair, fur and other keratinic fibers with dihydroxyaminobenzenes Expired - Lifetime US3011858A (en)

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DE (1) DE1135417B (en)
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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3236734A (en) * 1959-01-20 1966-02-22 Oreal Process for dyeing hair with aromatic aminohydroxyl derivatives
US3485568A (en) * 1961-09-25 1969-12-23 Oreal 2,5 - dihydroxy - monomethyl- or diethyl-aminobenzene for dyeing living human hair,furs and other keratinous fibers
US3546293A (en) * 1962-07-11 1970-12-08 Oreal Amino phenols
US3617167A (en) * 1965-08-05 1971-11-02 Therachemie Chem Therapeut Methods and compositions containing 4-aminopyrazolones for the dyeing of human hair
US3649159A (en) * 1968-06-03 1972-03-14 Fmc Corp Hair coloring method using a peroxydiphosphate oxidant
US3898032A (en) * 1971-06-11 1975-08-05 Zotos Int Inc Oxidative hair-coloring mixtures containing a conditioning agent
US4529404A (en) * 1976-06-30 1985-07-16 Clairol Incorporated Hair dye preparation

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE80814C (en) *
DE256794C (en) *
DE179881C (en) * 1905-06-21
NL69995C (en) * 1946-12-14

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3236734A (en) * 1959-01-20 1966-02-22 Oreal Process for dyeing hair with aromatic aminohydroxyl derivatives
US3485568A (en) * 1961-09-25 1969-12-23 Oreal 2,5 - dihydroxy - monomethyl- or diethyl-aminobenzene for dyeing living human hair,furs and other keratinous fibers
US3546294A (en) * 1961-09-25 1970-12-08 Oreal 2,5-dihydroxy-monomethyl- or -diethylamino benzene and the salts thereof
US3546293A (en) * 1962-07-11 1970-12-08 Oreal Amino phenols
US3617167A (en) * 1965-08-05 1971-11-02 Therachemie Chem Therapeut Methods and compositions containing 4-aminopyrazolones for the dyeing of human hair
US3649159A (en) * 1968-06-03 1972-03-14 Fmc Corp Hair coloring method using a peroxydiphosphate oxidant
US3898032A (en) * 1971-06-11 1975-08-05 Zotos Int Inc Oxidative hair-coloring mixtures containing a conditioning agent
US4529404A (en) * 1976-06-30 1985-07-16 Clairol Incorporated Hair dye preparation

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CH348784A (en) 1960-09-15
GB857070A (en) 1960-12-29
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NL238044A (en)

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