US3184387A - Process for dyeing hair with substituted 2, 4-diaminophenols - Google Patents

Process for dyeing hair with substituted 2, 4-diaminophenols Download PDF

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US3184387A
US3184387A US857989A US85798959A US3184387A US 3184387 A US3184387 A US 3184387A US 857989 A US857989 A US 857989A US 85798959 A US85798959 A US 85798959A US 3184387 A US3184387 A US 3184387A
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hair
dyeing
compound
diaminophenols
substituted
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US857989A
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Seemuller John Robert
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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

Definitions

  • This invention relates to the dyeing of animal fibres, and more especially the dyeing of live hair, by the use of polyaminophenol compounds and derivatives thereof.
  • oxidation dyes which are not true dyes but products which, on oxidation, give colored derivatives.
  • the known oxidation dyes are generally aromatic polyamines and/or polyaminophenols.
  • oxidation dyes a solution of such a dye is mixed, a short time before use, with an oxidizing solution, for example dilute hydrogen peroxide, and the mixture is then applied to the hair to be dyed. Satisfactory results are obtained, but this method offers the disadvantage that the treatment is of excessively long duration, the hydrogen peroxide tends to act deleteriously on the substance of the hair during the application, and it is necessary to store the working solutions in separate bottles.
  • R and R designate a member of the group consisting of a hydrogen atom, a lower alkyl group or a lower hydroxyalkyl group; one or the other of the groups R and R must be other than hydrogen.
  • a process for dyeing live hair comprises applying to the fibres a solution of a compound of the aforesaid general formula, allowing the oxygen of the ambient air to act on the hair impregnated with the compound for a time sufiicient to the desired development of the shade, and thereafter rinsing the hair.
  • aqueous solution of these compounds or of their derivatives is prepared, the pH of the solution is adjusted with the aid of an alkali, for example ammonium hydroxide, and the solution is applied to the fibres to be dyed, for example to the human hair.
  • an alkali for example ammonium hydroxide
  • the fibre is dyed to a shade depending upon the derivative chosen.
  • the process is very simple, avoids the use of an oxidizing agent such as dilute hydrogen peroxide, and permits dyeing at room temperature.
  • the present invention further provides compositions for application to animal fibres for dyeing the same, comprising an aqueous solution of a compound of the aforesaid general formula adjusted to a pH value of 5 to 8.
  • This compound is then reduced to obtain the desired compound, which is isolated in the form of its sulphate, melting at C.
  • This compound is prepared in the following manner: N-methyl-paraminophenol is acetylated, then nitrated by the classical method. Then it is deacetylated to obtain the 4-methy1amino-Z-nitrophenol, which gives by reduction using the usual technique, the 4-methylamino-2-aminophenol which is isolated as the sulphate.
  • Dyeing This material is used in a manner analogous to that described in the preceding examples.
  • a 3% sulphate solution is applied to live human hair having a pH adjusted to 8 by the addition of ammonium hydroxide. This allows the dyeing of white hair a deep blue shade.
  • a process for dyeing live human hairr which comprises: applying thereto an aqueous solution as an oxi- V "'dative dyestutf containing Z-methylamino-4aminophenol,
  • a process for dyeing live human hair which com prises: applying to the hair an aqueous solutionas an oxidative dye stuff adjusted to a pH of 5 to 8 of a sulphate of a compound of the formula I THRI wherein R and R are selected fromthe group consisting of hydrogen, lower alkyl and lower hydroxy alkyl, and at least one of R and R are other than hydrogen, thereafter said hair is aerated to promote the substantial oxi dation of this compound before being rinsed.

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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)

Description

3,184,387 PROCESS FOR DYEING HAIR WITH SUBSTITUTED 2,4-DIAMINOPHENOLS John Robert Seemuller, Maisons-Lafitte, Seine et Oise, France, assignor to LOreal, a corporation of France N Drawing. Filed Dec. 7, 1959, Ser. No. 857,989 Claims priority, application France, Nov. 25, 1955, 703,367, Patent 1,137,922; Oct. 18, 1956, 57,825 Claims. (Cl. 167--88) This application is a continuation-in-part of my copending application of Serial No. 623,773, filed November 23, 1956, which application is now abandoned.
This invention relates to the dyeing of animal fibres, and more especially the dyeing of live hair, by the use of polyaminophenol compounds and derivatives thereof.
It has long been known to elfect the dyeing of hair with the aid of so-called oxidation dyes, which are not true dyes but products which, on oxidation, give colored derivatives. The known oxidation dyes are generally aromatic polyamines and/or polyaminophenols.
Generally in using oxidation dyes a solution of such a dye is mixed, a short time before use, with an oxidizing solution, for example dilute hydrogen peroxide, and the mixture is then applied to the hair to be dyed. Satisfactory results are obtained, but this method offers the disadvantage that the treatment is of excessively long duration, the hydrogen peroxide tends to act deleteriously on the substance of the hair during the application, and it is necessary to store the working solutions in separate bottles.
It has now been found that polyaminophenols of the general formula:
wherein R and R designate a member of the group consisting of a hydrogen atom, a lower alkyl group or a lower hydroxyalkyl group; one or the other of the groups R and R must be other than hydrogen.
These compounds have remarkable properties as oxidation dyes for the dyeing of animal fibres and more especially of the human hair. The said compounds oxidize rapidly in the air so that the use of an auxiliary oxidizing agent, such as hydrogen peroxide, is avoided, together with the concomitant disadvantages referred to above.
According to the present invention therefore, a process for dyeing live hair comprises applying to the fibres a solution of a compound of the aforesaid general formula, allowing the oxygen of the ambient air to act on the hair impregnated with the compound for a time sufiicient to the desired development of the shade, and thereafter rinsing the hair.
An aqueous solution of these compounds or of their derivatives is prepared, the pH of the solution is adjusted with the aid of an alkali, for example ammonium hydroxide, and the solution is applied to the fibres to be dyed, for example to the human hair. By simple exposure to the ambient air, the fibre is dyed to a shade depending upon the derivative chosen. The process is very simple, avoids the use of an oxidizing agent such as dilute hydrogen peroxide, and permits dyeing at room temperature.
The present invention further provides compositions for application to animal fibres for dyeing the same, comprising an aqueous solution of a compound of the aforesaid general formula adjusted to a pH value of 5 to 8.
United States Patent 0 Patented May 18, 1965 "ice EXAMPLE I 2-methylamin0-4-aminophenol EXAMPLE II 4-beta-hydr0xyethylamino-Z-aminophenol NIL-011 011 011 Potassium 2-nitro-4-aminophenate is condensed with glycol chlorohydrin in alcoholic solution. There is thus obtained 4-beta-hydr0xyethylamino-2-nitropheno1 melting at 114115 C.
Analysis:
Element Calculated Found C. 48. 5 48. 3 I 5. 05 4. 86 N 14.14 14. 21
This compound is then reduced to obtain the desired compound, which is isolated in the form of its sulphate, melting at C.
Dyeing.-By operating under conditions similar to those of the foregoing example a beautiful violet shade is obtained on live hair.
EXAMPLE III 4-methylamino-2-amin0phenol NH-CH;
This compound is prepared in the following manner: N-methyl-paraminophenol is acetylated, then nitrated by the classical method. Then it is deacetylated to obtain the 4-methy1amino-Z-nitrophenol, which gives by reduction using the usual technique, the 4-methylamino-2-aminophenol which is isolated as the sulphate.
Dyeing.-This material is used in a manner analogous to that described in the preceding examples. A 3% sulphate solution is applied to live human hair having a pH adjusted to 8 by the addition of ammonium hydroxide. This allows the dyeing of white hair a deep blue shade.
In order to clearly show the particular possibilities of the use of the compounds according to the invention, all
. 3 V the dyeing tests described in the foregoing examples were carried out without any oxidizing agent other than atmospheric oxygen.
' What is claimed is:
1. A process for dyeing live human hair which com-.
prises: applying to the-hair an aqueous solution as' an oxidative dye stuff of a compound of'the formula NHRr wherein R and R are selected from the group consisting of hydrogen, lower alkyl and lower hydroxy alkyl, and at '3. A process for dyeing live human hairrwhich comprises: applying thereto an aqueous solution as an oxi- V "'dative dyestutf containing Z-methylamino-4aminophenol,
least one of R and R are other than hydrogen, thereafter said hair is aerated to promote the substantial oxidation of this compound before being rinsed. 1
2. A process for dyeing live human hair which com prises: applying to the hair an aqueous solutionas an oxidative dye stuff adjusted to a pH of 5 to 8 of a sulphate of a compound of the formula I THRI wherein R and R are selected fromthe group consisting of hydrogen, lower alkyl and lower hydroxy alkyl, and at least one of R and R are other than hydrogen, thereafter said hair is aerated to promote the substantial oxi dation of this compound before being rinsed.
7 May 1954, pp. 345-348.
thereafter said hair is aerated to promote the substantial oxidation of this compound before being rinsed.
prises: applying thereto an aqueous solution, as an oxidative dye stuff, containing 4-methylarnino-2eaminophenol,
' thereafter said hairis aerated to promote the substantial oxidation of this compound before beingrinsed.
References Cited by the Examiner UNITED STATES PATENTS 7 1,853,455 7 4/32 Reddelien et a1. 260573 FOREIGN PATENTS 7/11 France. 7
Addition to 413,877.
OTHER REFERENCES Chemical Abstracts, vol. 12: 1781 1918 Heilingotter: Am. Perfumer and Essential Oil Review,
Kaas I: Am. Perfumer and Aromatics, 68: 1, July 1956, 25-28.
Wood: Chemical Abstracts, vol. 46 (1952), col. 10117i.
JULIAN s. LEVITT, Primary Examiner.
.S. ROSEN, FRANK CACCIAPAGLIA, JR., LEWIS GOTTS, Examiners. v

Claims (1)

1. A PROCESS FOR DYEING LIVE HUMAN HAIR WHICH COMPRISES: APPLYING TO THE HAIR AN AQUEOUS SOLUTION AS AN OXIDATIVE DYE STUFF OF A COMPOUND OF THE FORMULA
US857989A 1955-11-25 1959-12-07 Process for dyeing hair with substituted 2, 4-diaminophenols Expired - Lifetime US3184387A (en)

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3666812A (en) * 1962-07-11 1972-05-30 Oreal Diamino phenol hair dyeing compounds
US4196145A (en) * 1973-10-15 1980-04-01 Clairol Incorporated Dyeing keratin fibers with 2-substituted m-toluenediamines
US4213758A (en) * 1977-01-20 1980-07-22 Henkel Kommanditgesellschaft Auf Aktien Oxidation hair dyes based upon tetraaminopyrimidine developers and couplers therefor
US4259261A (en) * 1976-08-20 1981-03-31 L'oreal Metaphenylenediamines
US4612396A (en) * 1984-06-20 1986-09-16 Hoechst Aktiengesellschaft Process for the preparation of pure 2-ethylamino-4-nitro-1-alkoxybenzenes
AU601482B2 (en) * 1986-10-15 1990-09-13 Bristol-Myers Squibb Company Process for coloring keratinaceous materials
US5676706A (en) * 1994-10-27 1997-10-14 Akram; Mustafa Substituted diaminophenols, and hair dyes containing such compounds
WO2002005767A1 (en) * 2000-07-17 2002-01-24 Henkel Kommanditgesellschaft Auf Aktien Oxidised hair colouring agents containing at least one disubstituited 2.4-diamino phenyl ether as a coupling component

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR413877A (en) * 1909-10-23 1910-08-20 Anilin Fabrikation Ag Method and compositions for dyeing hair and fur
FR14113E (en) * 1910-03-21 1911-09-23 Anilin Fabrikation Ag Method and compositions for dyeing hair and fur
US1853455A (en) * 1929-08-19 1932-04-12 Agfa Ansco Corp Photographic developer

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR413877A (en) * 1909-10-23 1910-08-20 Anilin Fabrikation Ag Method and compositions for dyeing hair and fur
FR14113E (en) * 1910-03-21 1911-09-23 Anilin Fabrikation Ag Method and compositions for dyeing hair and fur
US1853455A (en) * 1929-08-19 1932-04-12 Agfa Ansco Corp Photographic developer

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3666812A (en) * 1962-07-11 1972-05-30 Oreal Diamino phenol hair dyeing compounds
US4196145A (en) * 1973-10-15 1980-04-01 Clairol Incorporated Dyeing keratin fibers with 2-substituted m-toluenediamines
US4259261A (en) * 1976-08-20 1981-03-31 L'oreal Metaphenylenediamines
US4213758A (en) * 1977-01-20 1980-07-22 Henkel Kommanditgesellschaft Auf Aktien Oxidation hair dyes based upon tetraaminopyrimidine developers and couplers therefor
US4612396A (en) * 1984-06-20 1986-09-16 Hoechst Aktiengesellschaft Process for the preparation of pure 2-ethylamino-4-nitro-1-alkoxybenzenes
AU601482B2 (en) * 1986-10-15 1990-09-13 Bristol-Myers Squibb Company Process for coloring keratinaceous materials
US5676706A (en) * 1994-10-27 1997-10-14 Akram; Mustafa Substituted diaminophenols, and hair dyes containing such compounds
US5990355A (en) * 1994-10-27 1999-11-23 Hans Schwarzkopf Gmbh & Co. Kg. Substituted diaminophenols, process for their preparation, and hair dyes containing such compounds
WO2002005767A1 (en) * 2000-07-17 2002-01-24 Henkel Kommanditgesellschaft Auf Aktien Oxidised hair colouring agents containing at least one disubstituited 2.4-diamino phenyl ether as a coupling component

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