US3649158A - Process for dyeing locks of human hair with tetragolium salts - Google Patents

Process for dyeing locks of human hair with tetragolium salts Download PDF

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Publication number
US3649158A
US3649158A US749958A US3649158DA US3649158A US 3649158 A US3649158 A US 3649158A US 749958 A US749958 A US 749958A US 3649158D A US3649158D A US 3649158DA US 3649158 A US3649158 A US 3649158A
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United States
Prior art keywords
hair
dyeing
solution
rinsed
process according
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Expired - Lifetime
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US749958A
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English (en)
Inventor
Gregoire Kalopissis
Andree Bugaut
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LOreal SA
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LOreal SA
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Classifications

    • 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
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/06Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065Preparations for temporary colouring the hair, e.g. direct dyes
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916Natural fiber dyeing
    • Y10S8/917Wool or silk

Definitions

  • compositions which contain compounds which are colorless and soluble in water when in a reduced state, but capable of being transformed, when oxidized, into colored pigments which are insoluble in water.
  • coloring compositions are those based on oxidation dyes and on vat dyes.
  • the present invention relates to the use of compounds for dyeing keratinic fibers which, in contradistinction to those heretofore in use, are colorless and soluble in water when oxidized, but are insoluble or nearly so in water, and very strongly colored when reduced.
  • the dyes of this type have several advantages when used to dye keratinic fibers, and particularly human hair. When in their colorless, oxidized form, they penetrate the keratinic fibers very well and have a great afiinity for them, so that the hair may be washed immediately after impregnation with one of these colorless dyeing compositions, and the color then developed by reduction.
  • n is a whole number equal to 1 or 2
  • R and R" represent aromatic radicals which may be substituted by groups such as nitro, methoxy and halogen groups;
  • R regardless of the value of n, represents hydrogen
  • Y represents:
  • A represents an anion, such for example, as a halide
  • thecolor is brought out by applying a reducing solution which transforms the said tetrazolium salt or salts into colored insoluble formazanes, according to the reaction:
  • the reducing agents which may be used in accordance with 75 I 3,3 .929 tent r the s e sy whis h e y qit e vsi tion potentials lower than those of formazane/tetrazolium salt systems.
  • the reducing agents which may be used in carrying out the invention may be those which do not have any effect on the structure of the keratin of the hair, and specifically not on the S-S bonds, that is to say, soft reducing agents such as ascorbic acid, hydrazine, dithionic acids, and the reductones.
  • reducing agents such as thiols or borohydrides, which can disrupt the SS bonds of the keratin, but preferably in such weak concentrations, that they have practically no chemical effect on the hair.
  • Colorless compounds which do not react with the keratin and which are transformed into colored compounds by oxidation such as leuco derivatives, or oxidation dyes may also be used as reducing agents.
  • the reducing agents of the leuco-derivative type or the oxidation dyes may act as shade varying means.
  • a colored permanent wave may be effected by utilizing the properties of tetrazolium salts.
  • the hair may first be treated with a conventional reducing agent, rinsed, and treated with a solution of tetrazolium salt which, by reacting with the reducing groups in the hair, are transformed into formazane and develop a color. If so desired, an oxidizing agent may then be applied to carry out the second step of a conventional permanent.
  • a solution of tetrazolium salts is applied to the hair, after which a conventional permanent waving process is carried out, that is to say, a reducing solution is applied, which transforms the tetrazolium salts into forrnazanes and so develops the color.
  • a conventional permanent waving process that is to say, a reducing solution is applied, which transforms the tetrazolium salts into forrnazanes and so develops the color.
  • the second step of a permanent waving process that is to say, the application of a conventional oxidizing agent, may then be carried out, if desired.
  • a further object of the invention is to provide a hair dyeing composition characterized by the fact that it contains at least one tetrazolium salt, as above defined.
  • tetrazolium salts which may be used in accordance with the present invention are the following, but this list is not exhaustive:
  • composition contains from 0.1 to 10 percent of tetrazolium salts.
  • the pH value of the composition is basic, that is to say, greater than 7.
  • composition according to the invention may also contain any additives which are conventionally used in dyeing solutions. They may take the form of aqueous or hydroalcoholic solutions, creams, gels, or aerosols.
  • tetrazolium salts which may be used in carrying out the invention, a certain number have the characteristic of forming photosensitive formazanes, that is to say formazanes which are unstable in the presence of light. in this particular case the colors obtained are transient and make it possible to apply shades to the hair which are of short duration, and are then eliminated without any need to resort to a bleach.
  • transient dyeing compounds according to the invention have the advantage over those transient dyeing compounds heretofore known that they degrade progressively with out changing the color of the hair, their disappearance being evidenced only by a progressive decrease in the intensity of the color.
  • This solution is applied to 90 percent white hair, and left to act for 15 minutes, after which the hair is rinsed.
  • the hair is then rinsed and shampooed.
  • thioglycnlic acid 5 g. ammonia q.s.p. pH 7.7 water q.s.p. 100 g.
  • a deep red color is produced at once, and resists subsequent shampooings.
  • Solution 2 hydrazine 0.3 5. water. q.s.p. 100 g.
  • Solution l 3,3'-para (di-orthornethoxy) diphenylene-LZ ',S,S -tetmv phenyl-ditctrazolium dichloride lwater q.s.p. N30 Solution 2: alloxantine 0.32 g.
  • the two solutions are mixed in equal quantities, so that they are in equimolecular proportions.
  • a lock of 90 percent white hair is impregnated with this solution, and left to act for 15 minutes. The hair is then rinsed.
  • a 3 percent solution of sodium hydrosulfite, brought to pH by the addition of sodium hydroxide is then applied. This is left to act for 5 minutes, after which the hair is rinsed and shampooed. A deep blue grey results.
  • the two solutions are mixed in equal quantities, i.e., in equimolecular proportions.
  • the mixture has a pH value of about 7.
  • This mixture is applied to 90 percent white hair, and left to act for minutes. The hair is then rinsed and shampooed. A deep grey black results.
  • a process for dyeing locks of human hair which comprises the step of impregnating the hair with at least one composition containing from about 0.1 to 10 percent of a tetrazolium salt responding to the formula:
  • n is a whole number between 1 and 2 inclusive
  • R is a radical selected from the group consisting of phenylene and a phenylene substituted by a substituent selected from the group consisting of nitro and methoxy radicals;
  • R" is a radical selected from the group consisting of phenyl and a phenyl substituted by a substituent selected from the group consisting of nitro and methoxy radicals;
  • R is selected from the group consisting of hydrogen, phenyl, and a phenyl radical substituted by a substituent selected from the group consisting of nitro and methoxy radicals;
  • the reducing solution contains a reducing agent selected from the group consisting of ascorbic acid, hydrazine, dithionic acids, reductones, borohydrides, thiols, sodium ascorbates, forrnamidine sulfinic acid, alloxanthine, aminohydroquinone hydrobromide, and sodium hydrosulfite.
  • a reducing agent selected from the group consisting of ascorbic acid, hydrazine, dithionic acids, reductones, borohydrides, thiols, sodium ascorbates, forrnamidine sulfinic acid, alloxanthine, aminohydroquinone hydrobromide, and sodium hydrosulfite.

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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)
US749958A 1967-08-08 1968-08-05 Process for dyeing locks of human hair with tetragolium salts Expired - Lifetime US3649158A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
LU54267 1967-08-08
LU55016 1967-12-04

Publications (1)

Publication Number Publication Date
US3649158A true US3649158A (en) 1972-03-14

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US749958A Expired - Lifetime US3649158A (en) 1967-08-08 1968-08-05 Process for dyeing locks of human hair with tetragolium salts

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US (1) US3649158A (enrdf_load_stackoverflow)
BE (1) BE719055A (enrdf_load_stackoverflow)
CH (1) CH489247A (enrdf_load_stackoverflow)
DE (1) DE1769916C3 (enrdf_load_stackoverflow)
FR (1) FR1584111A (enrdf_load_stackoverflow)
GB (1) GB1228634A (enrdf_load_stackoverflow)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5161553A (en) * 1986-09-19 1992-11-10 Clairol Incorporated Process for simultaneously waving and coloring hair
US5782933A (en) * 1997-04-30 1998-07-21 Bristol-Myers Squibb Company Ascorbic and isoascorbic acids to remove or adjust oxidative color in hair
US20060277693A1 (en) * 2005-05-31 2006-12-14 Jean-Baptiste Saunier Composition for dyeing keratin fibers, comprising at least one diamino-N,N-dihydropyrazolone derivative, at least one coupler and at least one associative polyurethane polymer
US20060277691A1 (en) * 2005-05-31 2006-12-14 Jean-Baptiste Saunier Composition for dyeing keratin fibers, comprising a diamino-N,N-dihydropyrazolone compound, a coupler, and a polyol
US20060277692A1 (en) * 2005-05-31 2006-12-14 Jean-Baptiste Saunier Composition for dyeing keratin fibers, comprising at least one diamino-N,N-dihydropyrazolone derivative, at least one coupler, and at least one surfactant
EP1859782A1 (de) * 2006-05-24 2007-11-28 Henkel Kommanditgesellschaft auf Aktien Aufhell- und/oder Färbemittel mit Tetrazolen
WO2007121852A3 (de) * 2006-04-19 2008-04-17 Henkel Kgaa Aufhell- und/oder färbemittel mit amidinen
US7582121B2 (en) 2005-05-31 2009-09-01 L'oreal S.A. Composition for dyeing keratin fibers, comprising at least one diamino-N,N-dihydropyrazolone derivative, at least one coupler, and at least one heterocyclic direct dye
FR3105734A1 (fr) * 2019-12-30 2021-07-02 L'oreal Procédé de traitement des fibres kératiniques comprenant l’application d’une composition comprenant un composé particulier et une étape d’apport énergétique auxdites fibres kératiniques

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3185567A (en) * 1959-07-06 1965-05-25 Polaroid Corp Photographic color process and product
US3257205A (en) * 1960-10-12 1966-06-21 Gevaert Photo Prod Nv Method for heat development
US3297709A (en) * 1965-11-19 1967-01-10 American Home Prod Certain substituted tetrazole derivatives
US3396736A (en) * 1961-03-16 1968-08-13 Turner Hall Corp Fiber reactive dyestuff composition and methods of dyeing human hair therewith

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3185567A (en) * 1959-07-06 1965-05-25 Polaroid Corp Photographic color process and product
US3257205A (en) * 1960-10-12 1966-06-21 Gevaert Photo Prod Nv Method for heat development
US3396736A (en) * 1961-03-16 1968-08-13 Turner Hall Corp Fiber reactive dyestuff composition and methods of dyeing human hair therewith
US3297709A (en) * 1965-11-19 1967-01-10 American Home Prod Certain substituted tetrazole derivatives

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5161553A (en) * 1986-09-19 1992-11-10 Clairol Incorporated Process for simultaneously waving and coloring hair
US5782933A (en) * 1997-04-30 1998-07-21 Bristol-Myers Squibb Company Ascorbic and isoascorbic acids to remove or adjust oxidative color in hair
US7488355B2 (en) 2005-05-31 2009-02-10 L'oreal S.A. Composition for dyeing keratin fibers, comprising a diamino-N,N-dihydropyrazolone compound, a coupler, and a polyol
US20060277691A1 (en) * 2005-05-31 2006-12-14 Jean-Baptiste Saunier Composition for dyeing keratin fibers, comprising a diamino-N,N-dihydropyrazolone compound, a coupler, and a polyol
US20060277692A1 (en) * 2005-05-31 2006-12-14 Jean-Baptiste Saunier Composition for dyeing keratin fibers, comprising at least one diamino-N,N-dihydropyrazolone derivative, at least one coupler, and at least one surfactant
US7485156B2 (en) 2005-05-31 2009-02-03 L'oreal S.A. Composition for dyeing keratin fibers, comprising at least one diamino-N,N-dihydropyrazolone derivative, at least one coupler and at least one associative polyurethane polymer
US7488356B2 (en) 2005-05-31 2009-02-10 L'oreal S.A. Composition for dyeing keratin fibers, comprising at least one diamino-N,N-dihydropyrazolone derivative, at least one coupler, and at least one surfactant
US20060277693A1 (en) * 2005-05-31 2006-12-14 Jean-Baptiste Saunier Composition for dyeing keratin fibers, comprising at least one diamino-N,N-dihydropyrazolone derivative, at least one coupler and at least one associative polyurethane polymer
US7582121B2 (en) 2005-05-31 2009-09-01 L'oreal S.A. Composition for dyeing keratin fibers, comprising at least one diamino-N,N-dihydropyrazolone derivative, at least one coupler, and at least one heterocyclic direct dye
WO2007121852A3 (de) * 2006-04-19 2008-04-17 Henkel Kgaa Aufhell- und/oder färbemittel mit amidinen
EP1859782A1 (de) * 2006-05-24 2007-11-28 Henkel Kommanditgesellschaft auf Aktien Aufhell- und/oder Färbemittel mit Tetrazolen
FR3105734A1 (fr) * 2019-12-30 2021-07-02 L'oreal Procédé de traitement des fibres kératiniques comprenant l’application d’une composition comprenant un composé particulier et une étape d’apport énergétique auxdites fibres kératiniques
WO2021136788A1 (en) * 2019-12-30 2021-07-08 L'oreal Process for treating keratin fibres, comprising the application of a composition comprising a particular compound comprising at least two tetrazoles groups

Also Published As

Publication number Publication date
GB1228634A (enrdf_load_stackoverflow) 1971-04-15
FR1584111A (enrdf_load_stackoverflow) 1969-12-12
DE1769916B2 (de) 1978-06-01
DE1769916A1 (de) 1971-07-29
BE719055A (enrdf_load_stackoverflow) 1969-02-05
DE1769916C3 (de) 1979-01-25
CH489247A (fr) 1970-04-30

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