US3041244A - Quinone hair dye compositions - Google Patents

Quinone hair dye compositions Download PDF

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US3041244A
US3041244A US68442657A US3041244A US 3041244 A US3041244 A US 3041244A US 68442657 A US68442657 A US 68442657A US 3041244 A US3041244 A US 3041244A
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sodium
hair
dye
water
quinone
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Jerome A Feit
Aloysius J Feit
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Jerome A Feit
Aloysius J Feit
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35Ketones, e.g. benzophenone
    • A61K8/355Quinones
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/19Cosmetics or similar toilet preparations characterised by the composition containing inorganic ingredients
    • A61K8/26Aluminium; Compounds thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/72Cosmetics or similar toilet preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73Polysaccharides
    • A61K8/733Alginic acid; Salts thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/10Preparations for permanently dyeing the hair

Description

United States Patent 3,041,244 QUINONE HAIR DYE COMPOSITION Jerome A. Feit,.5tl N. Kildare Ave, and Aloysius J. Feit, 5601 N. Lowell Ave., Chicago 30, Ill. No Drawing. Filed Sept. 17, 1957, Ser. No. 684,426 9 Claims. (01. 167-88) This invention relates to the dyeing of hair on the human head and is particularly concerned with new and improved hair dye compositions therefor.

Various types of hair dyes and hair dyeing and coloring compositions have been suggested over a period of many years and various of them have come into use. Among the organic dyes which have found varying favor from time to time in hair dyeing compositions are those of vegetable, coal tar, and synthetic origin, basic and direct dyes, including those of the type of paraphenyleno diamine and para-diaminophenol, azo dyes, and triphenylmethane dyes, etc. rogallol with soluble salts of various metals such as lead, silver, iron, nickel, copper, bismuth, mercury, and still others, have at times been used but they have fallen into disfavor due to their poisonous nature, their interference with the cold waving of hair and restrictive Government regulations. The hair dye compositions which are in largest use and Which have met with the greatest reception at the present time are those which utilize so-called para dyes, such as paraphenylenediamine and para-diaminophenol, mentioned above, as well as others of this type such as metaphenylenediamine, and ortho, metaand para-toluenediamine, and the acid salts thereof as well, also, as sulfonic derivatives of cer tain of said para dyes. The said para dyes are conventionally applied to the hair in solution with hydrogen peroxide or the hydrogen peroxide is applied immediately after the subjection of the hair to contact with the para dyes. Because the para dyes are toxic to some persons, it is necessary to resort to the so-called patch test to determine preliminarily whether the particular individual involved may be adversely affected by the hair dye. This, and the requirement by law for the placement of a caution notice on the packages of such dyes, has left much to be desired in the way of achieving fully satisfactory hair dye compositions which give good results and are essentially free from toxic effects. Indeed, it may safely be said that no hair dye compositions have yet been evolved which are capable of simple use by the woman in the home which give good dyeing results and which effectively eliminate the problem of toxicity to the user.

Suggestions have also been made broadly to utilize anthraquinone dyes in hair dyeing compositions, but no effective way was found to obtain satisfactory hair dye compositions containing anthraquinone dyes, and such compositions have not gone into commercial use.

In accordance with the present invention, new and highly improved hair dye compositions have been evolved which achieve excellent dyeing results, are simple to use, and are materially freer from toxic effects such as commonly characterize the para dyes. The hair dye compositions of the present invention are made, for marketing, in the form of dry compositions, and in use are employed particularly in the form of freshly prepared pastes, although they can also, with less convenience, be utilized in the form of freely .fiowing liquids. They are characterized by 'the presence, as essential ingredients, of a synthetic nontoxic quinone dye which is or has been rendered water-soluble 'or water-dispersible, a water-soluble Formulations based on tannin or py' A 3,041,244 Patented June 26, 1962 ice The synthetic nontoxic quinone dyes which are utilizedin accordance with the present invention may contain one, two or three rings, any one or more of whichmay comprise quinone rings. In order to be effective for the purposes of this invention, the said quinone dyes must be'water-soluble or water-dispersible or rendered Watersoluble or water-dispersible. Their molecules may con tain substituent groups, for instance, hydroxyl, carboxyl, amino, nitro and sulfonic. Such groups serve to enhance the water-solubility of the quinone dyes, the sulfonic groups generally speaking being most effective in this regard but they tend to diminish the afiinity of the quinones for the hair. The quinone dyes may also contain alkyl and halogen, such as chlorine and bromine, groups. These substituent groups, as well as various of those previously mentioned, affect not only the water-solubility but also the shades of colors obtained on the hair. Typical or illustrative examples of synthetic nontoxic quinone dyes which produce good results, when used in accordance with the principles of this invention, are benzoquinones,

naphthoquinones and anthraquinones such as hyclroq'uinone; 1,4-naphthoquinone; 1,2-naphthoquinone; 2,6-dichloroquinonechlorimide; N-chloro-p-quinone-chlorimide;

tert F butylhydroxyquinone; 1,2 dihydroxyanthraquinone; tetrachloroquinone; 1,2-dihydroXy-3-nitroanthraquinone; 1,4-diaminodihydroanthraquinone; N-chloro-p quinoneimine; and 'various mixtures of two or more thereof.

Modifications of the shades of the hair dyes can be obtained by including with the synthetic nontoxic quinones various agents as, for instance, tannic acid and phenols and naphthols such as resorcinol, catechol, 2- amino F l naphthol, 4 amino 1 naphthol and 8- amino-I-naphthol; and aminosalicylic acid. In some cases, the inclusion of certain naphthols has resulted in new dyes or colors as, for example, in the case of 8- amino-I-naphthol and tetrachloroquinone which produces a green shade whereas naphthol alone gives a brown shade and tetrachloroquinone alone gives a tan shade.

The water-soluble dispersing agent or surface active agent serves, among other purposes, to enhance the solubility of the quinones and to increase the afiinity of the quinone dyes for the hair. Numerous agents of that type are readily available as, for instance, higher alkyl benzene sulfonates such as dodecyl benzene sodium sulfonate; alkyl naphthalene sulfonates such as nonyl naphthalene sodium. sulfonate and isopropyl naphthalene sodium sulfonate; sulfonated esters of alcohols and polybasic acids as, for instance, dioctyl sodium sulfosuccinate, typical of such products being sold under the names Aerosol OT and Decerosol OT; taurates such as sodiumN- methyl-N-oleoyl taurate and sodium N-methyl-N-coconut oil fatty acid taurate, such products being sold under the name Igepon T; oleic acid ester of sodium isethionate, sold under the name Igepon AP-; fatty alcohol sulfates such as sodium dodecyl sulfate; sulfates of branched chain or secondary alcohols such as 7-ethyl-2-methylundecanol-4 sulfate, sodium salt, and 3,9-diethyl tridecanol- 6 sulfate, sodium salt, sold under the name Tergitol; naphthalene sulfonic acid condensates sold under the name Blancol N, and the like.

The thickening agents serve to make a paste of the dye compositions when used for the dyeing of the hair and make for convenient application and prevent the dye composition from running off the hair. No novelty is claimed broadly in using thickening agents hair dye compositions as this has broadly been known and pracbination with the other ingredients of the hair dye compositions of this invention, serves to increase the affinity of the hair for the dye ingredients. It is particularly preferred to use an alkaline reacting compound with oxidizing properties. Suitable alkaline reacting compounds are trisodium phosphate, sodium carbonate, tetrasodium pyrophosphate, sodium hexametaphosphate, sodium tripoly phosphates and sodium perborate. Sodium perborate is especially satisfactory because of its mildness, stability and the relatively low pH of its solutions, namely pH 9.9. It is particularly desirable that the alkalinity of the dye compositions fall within the range of 8 to 10.5.

The proportions of the ingredients are variable within reasonable limits. In general, the proportions set forth below, while not intended as limiting the invention, produce dye compositions which give excellent results. The percentages stated are by'weight:

Percent Synthetic nontoxic quinone dye (or dye mixture) 2 to 25 Water-soluble surface active agent .15 to 40 Thickening agent 3 to 15 Alkaline reacting compound 2 to 8 The especially preferred hair dye compositions of the present invention fall within the following compositional limits:

By increasing the amount of sodium alginate or the like and correspondingly reducing the bentonite, varying adjustments can be made in the thickness of the paste. It will be understood that various supplemental ingredients can be added, including perfumes, for obtaining special effects without departing from the novel teachings and principles set forth herein.

The following examples are illustrative of hair dye compositions made in accordance with this invention. It Will be understood that various other hair dye compositions can readily be evolved following the guiding principles and teachings set forth herein. All parts listed are by weight.

4 EXAMPLE 3 Dark Ash Blonde 1,2-naphthoquinone 7.0 5 Resorcinol 7.0 Nonyl naphthalene sodium sulfonate 35.0 Sodium alginate 10.0 Sodium perborate 5.0 Bentonite 36.0

EXAMPLE 4 Reddish Blonde Hydroquinone 10.0 Dodecyl benzene sodium sulfonate 35.0 Sodium alginate 10.0 Sodium perborate 5.0 Bentonite 40m EXAMPLE 5 Neutral Brown 2,-6-dichloroquinonechlorimide 13.0 Tert-butylhydroquinone 8.0 Sodium N-methyl-N-oleoyl taurate 35.0 Sodium alginate 10.0 Sodium perborate 5.0 Bentonite 29.0

EXAMPLE 6 3O Reddish Brown 1,2-naphthoquinone 10.0 p-toluquinone 10.0 Dodecyl benzene sodium sulfonate .0 Sodium alginate 10.0 35 Sodium perborate 5.0 Bentonite 30.0

EXAMPLE 7 Golden Blonde 4O Hydroquinone 8.0 2-amino-1,4-naphthoquinone 0.5 Isopropyl napthalene sodium sulfonate 35.0 Sodium alginate 10.0 Sodium perborate 5.0 Bentonite 41.5

EXAMPLE 8 Steel Grey Z-amino-l-naphthol 1.0 Tetradhloroquinone 2.0 1,4-diaminoanthraquinon e 3.0 Naphthalene sulfonic acid condensate 35.0 Sodium alginate 10.0 Sodium perborate 5.0 Bentonite 44.0

EXAMPLE 9 Pale Blonde 6O Hydroquinone 2.5 Aminosalicylic acid 2.5 Sodium N-Methyl-N-oleoyl taurate 35.0 Sodium alginate 10.0 Sodium perborate 5.0 5 Bentonite 45.0

EXAMPLE 10 Bright Red 1,2dihydroxy-3-nitroanthraquinone 10.0 1,4-diaminodihydroanthraquinone 1.0 Oleic acid ester of sodium isethionate 35.0 Sodium alginate 10.0 Sodium perborate 5.0

Bentonite 39.0

g EXAMPLE 11 Golden Brown 1,2-naphthoquinone 5.0 Resorcinol 5.0 'Dioctyl sodium sulfosuccinate 35.0 Sodium alginate A 10.0 Sodium perborate 5.0 Bentonite 40.0

EXAMPLE 12 Black N-chloro-p-quinoneimine 40.0 4-amino-1-naphtho1 1.0 8-amino-1-naphthol 0.4 Tetrachloroquinone 0.6 Lauryl sodium sulfate 35.0 Sodium alginate 10.0 Sodium perborate 5.0 Bentonite 8.0

EXAMPLE 13 Light Ash Brown 1,2-naphthoquinone 10.0 Resorcinol 20.0 Dodecyl benzene sodium sulfonate 35.0 Sodium alginate 10.0 Sodium perborate 5.0 Bentonite 20.0

EXAMPLE 14 Dark Brown N-chloro-p-quinoneimine 15.0 8-amino-1-naphthol 5.0 Tetrachloroquinone 10.0 Dodecyl benzene sodium sulfonate 35.0 Sodium alginate 10.0 Sodium perborate 5.0 Bentonite 20.0

In dyeing the hair with the novel hair dye compositions of the present invention, 1 gram of the hair dye composition of any of the foregoing examples is admixed with 4.5 cc. of water at 40 to 50 degrees C. The resulting paste is then applied to the hair and allowed to remain in contact therewith for from about 15 to 30 minutes while maintaining the temperature of the scalp at above 40 degrees C. to develop the full shade. Longer contact times are used where lower application temperatures are employed. The dye paste can be applied to the hair by means of a comb, brush, swab or the like. After the dye paste has been in contact with the hair for about 15 to 30 minutes, in the usual case, the hair is rinsed wth lukewarm water to remove excess dye composition and is then shampooed.

What is claimed as new and desired to be protected by Letters Patent of the United States is:

1. A hair dye in the form selected from the group consisting of an aqueous paste and of a dry composition which is adapted upon admixture with water to form a paste for application to the hair, said composition comprising a mixture containing a synthetic nontoxic watersoluble to dispersible quinone dye, a water-soluble surface active agent, bentonite, sodium alginate, and an alkaline reacting compound.

2. A hair dye in the form selected from the group consisting of an aqueous paste and of a dry composition which is adapted upon admixture with Water to form a paste for application to the hair, said composition comprising a mixture containing a synthetic nontoxic watersoluble to dispersible quinone dye, a water-soluble dispering surface active agent, bentonite, sodium alginate, and an alkaline reacting oxidizing agent.

3. A hair dye in the form selected from the group consisting of an aqueous paste and of a dry composition 6 which is adapted upon admixture with water to form a paste for application to the hair, said composition comprising a mixture containing a synthetic nontoxic watersoluble to dispersible quinone dye, a-water-soluble dispersing surface active agent, bentonite, sodium alginate, and sodium perbo-rate.

4. A hair dye in the form selected from the group consisting of an aqueous paste and of a dry composition which is adapted upon admixture with water to form a paste for application to the hair, said composition, on the dry basis, containing the following ingredients in substantially the following percentages by weight:

Percent Synthetic nontoxic water-soluble to dispersbile quinone dye 2 to 25 Water-soluble surface active agent 15 to 40 Thickening agent 3 to 15 Alkaline reacting compound 2 to 8 5. A hair dye composition in accordance with claim 4, wherein the quinone dye is selected from the group consisting of 1,4-naphthoquinone; 1,2-naphthoquinone; 2,6- dichloroquinonechlorimide; N-chloro-p-quinone chlorimide; tert-butylhydroxyquinone; 1,2-dihydroxyanthraquinone; tetrachloroquinone; 1,2-dihydroxy-3-nitroanthraquinone; 1,4-diaminodihydroanthraquinone; N-chloro-pquinoneimine; and compatible mixtures thereof.

'6. A hair dye in the form selected from the group consisting of an aqueous paste and of a dry composition which is adapted upon admixture with water to form a paste for application to the hair, said composition, on the dry basis, containing the following ingredients in substantially the following percentages by weight:

Percent Synthetic nontoxic water-soluble to dispersible quinone dye 8 to 25 Water-soluble surface active agent 15 to 40 Sodium alginate 3 to 15 Alkaline reacting oxidizing agent 2 to 8 7. A hair dye in the form selected from the group consisting of an aqueous paste and of a dry composition which is adapted upon admixture with water to form a paste for application to the hair, said composition, on the dry basis, containing the following ingredients in substantially the following percentages by weight:

Percent Synthetic nontoxic water-soluble to dispersible quinone dye 8 to 25 Water-soluble surface active agent 15 to 40 Sodium alginate 3 to 15 Sodium perborate 2 to 8 8. A hair dye in the form selected from the group consisting of an aqueous paste and of a dry composition which is adapted upon admixture with water to form a paste for application to the hair, said composition, on the dry basis, containing the following ingredients in substantially the following percentages by weight:

9. A hair dye composition in accordance with claim 8, wherein the quinone dye is selected from the group consisting of 1,4-naphthoquinone; 1,2-naphthoquinone; 2,6-

dichloroquinonechlorimide; N-chloro-p-quinone chlorimide; tert-butylhydroxyquinone; 1,2-clihydroxyanthraquinone; tetrachloroquinone; l,2-dihydroxy-3-nitroanthraquinone; 1,4-diaminodihydroanthraquinone; N-chloro-p-quinoneimine; and compatible mixtures thereof.

(References on following page) 7 8 References Cited in the file of this patent 2,776,668 Morgan Ian. 8, 1957 UNITED STATES PATENTS FOREIGN PATENTS girgc qnt gg. 1:, 13:; 687,227 Great Britain Feb. 11, 1953 u1s mg ept.

2,548,543 Mecco Apr. 10, 1951 5 OTHER REFERENCES 2,618,529 Luttringhaus et a1. Nov. 18, 1952 Harry: Cosmetic Materials, vol. 2, Leonard Hill Ltd., 2,695,259 Charle Nov. 23, 1954 London (1950), pp. 43-44. 2,745,788 lFrohnsdorfi et a1 May 15, 1956 AATC The pplication of Vat Dy Assno 2,763,269 Den Bests Sept. 18, 1956 Textile Chemists and Colorists (1953), pp. 31 and 166-9,

Claims (1)

  1. 4. A HAIR DYE IN THE FORM SELECTED FROM THE GROUP CONSISTING OF AN AQUEOUS PASTE AND OF A DRY COMPOSITION WHICH IS ADEQUATE UPON ADMIXTURE WITH WATER TO FORM A PASTE FOR APPLICATION TO THE HAIR, SAID COMPOSITION, ON THE DRY BASIS, CONTAINING THE FOLLOWING INGREDIENTS IN SUBSTANTIALLY THE FOLLOWING PERCENTAGES BY WEIGHT: PERCENT SYNTHETIC NONTOXIC WATER-SOLUBLE TO DISPERSBILE QUINONE DYE 2 TO 25 WATER-SOLUBLE SURFACE ACTIVE AGENT 15 TO 40 THICKENING AGENT 3 TO 15 ALKALINE REACTING COMPOUND 2 TO 8
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Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3168441A (en) * 1961-07-31 1965-02-02 Clairol Inc Blue anthraquinone dye
US3216899A (en) * 1958-11-13 1965-11-09 Wella Ag Hair dye comprising m-lower-dialkyl aminophenol and p-mononuclear diamines
US3251744A (en) * 1963-02-08 1966-05-17 Clairol Inc Naphthazarin hair dyeing composition and method
US3251742A (en) * 1962-05-14 1966-05-17 Revlon Method for coloring human hair with polyhydric aromatic compound, aromatic amine andan oxidation enzyme
US3330624A (en) * 1964-06-05 1967-07-11 Allied Chem Preparation of pyrosulfuryl fluoride and by-products
US3415607A (en) * 1965-03-01 1968-12-10 Warner Lambert Pharmaceutical Hair dye composition containing 2-hydroxy-1,4-naphthoquinone
DE3207036A1 (en) * 1981-02-27 1982-09-16 Oreal Hair dyes containing hydroxyanthrachinonverbindungen and a process for dyeing of human hair
FR2517200A1 (en) * 1981-12-02 1983-06-03 Oreal
FR2563215A1 (en) * 1984-04-20 1985-10-25 Shiseido Co Ltd Derived from naphthalene and composition of hair dye containing
EP0257399A2 (en) * 1986-08-13 1988-03-02 Beratungslabor für die kosmetische und pharmazeutische Industrie Dipl.-Ing. Karlheinz Schrader Hair dyeing composition
US4888026A (en) * 1981-12-02 1989-12-19 L'oreal Use of hydroxynaphthoquinones for dyeing human keratin fibres
US4895575A (en) * 1982-12-08 1990-01-23 L'oreal Use of 5-hydroxynaphthoquinones for dyeing human keratin fibres
US5259849A (en) * 1982-04-29 1993-11-09 L'oreal Composition based on quinone dyestuffs for use in hair dyeing and process for the preservation of quinone dyestuffs
US5785961A (en) * 1995-03-28 1998-07-28 Shiseido Company, Ltd. Mixing-at the time of use-type hair-treating composition
WO2002102336A1 (en) * 2001-06-19 2002-12-27 Wella Aktiengesellschaft Agent containing quinonimine derivatives and used to colour keratin fibres, and associated method
EP1982691A1 (en) * 2007-04-20 2008-10-22 KPSS-Kao Professional Salon Services GmbH Composition for coloring keratin fibres

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2382188A (en) * 1943-02-04 1945-08-14 Mathieson Alkali Works Inc Oxidation of vat and sulphur dyes
US2383990A (en) * 1941-11-21 1945-09-04 Quisling Sverre Prolamine coating materials
US2548543A (en) * 1949-11-30 1951-04-10 American Cyanamid Co Compositions and methods using reduction-sensitive vat dyes and inorganic nitrites
US2618529A (en) * 1949-12-31 1952-11-18 Gen Dyestuff Corp Application of leuco esters of vat dyestuffs on animal fibers using urea and an acid
GB687227A (en) * 1950-03-06 1953-02-11 Unilever Ltd Improvements in or relating to the dyeing of human hair
US2695259A (en) * 1949-01-03 1954-11-23 Union Francaise Commerciale Et Industrielle Sa Dermatologically harmless hair dyeing creams
US2745788A (en) * 1954-04-30 1956-05-15 Gillette Co Dyeing with quinones or hydroquinones and borohydrides and compositions therefor
US2763269A (en) * 1952-02-01 1956-09-18 Rayette Inc Foaming hair coloring compositions comprising basic dyes, and method of use
US2776668A (en) * 1951-06-28 1957-01-08 Rubinstein Inc H Method and preparations for the permanent dyeing of keratinous material

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2383990A (en) * 1941-11-21 1945-09-04 Quisling Sverre Prolamine coating materials
US2382188A (en) * 1943-02-04 1945-08-14 Mathieson Alkali Works Inc Oxidation of vat and sulphur dyes
US2695259A (en) * 1949-01-03 1954-11-23 Union Francaise Commerciale Et Industrielle Sa Dermatologically harmless hair dyeing creams
US2548543A (en) * 1949-11-30 1951-04-10 American Cyanamid Co Compositions and methods using reduction-sensitive vat dyes and inorganic nitrites
US2618529A (en) * 1949-12-31 1952-11-18 Gen Dyestuff Corp Application of leuco esters of vat dyestuffs on animal fibers using urea and an acid
GB687227A (en) * 1950-03-06 1953-02-11 Unilever Ltd Improvements in or relating to the dyeing of human hair
US2776668A (en) * 1951-06-28 1957-01-08 Rubinstein Inc H Method and preparations for the permanent dyeing of keratinous material
US2763269A (en) * 1952-02-01 1956-09-18 Rayette Inc Foaming hair coloring compositions comprising basic dyes, and method of use
US2745788A (en) * 1954-04-30 1956-05-15 Gillette Co Dyeing with quinones or hydroquinones and borohydrides and compositions therefor

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3216899A (en) * 1958-11-13 1965-11-09 Wella Ag Hair dye comprising m-lower-dialkyl aminophenol and p-mononuclear diamines
US3168441A (en) * 1961-07-31 1965-02-02 Clairol Inc Blue anthraquinone dye
US3251742A (en) * 1962-05-14 1966-05-17 Revlon Method for coloring human hair with polyhydric aromatic compound, aromatic amine andan oxidation enzyme
US3251744A (en) * 1963-02-08 1966-05-17 Clairol Inc Naphthazarin hair dyeing composition and method
DE1229251B (en) * 1963-02-08 1966-11-24 Clairol Inc Naphthazarin hair dye
US3330624A (en) * 1964-06-05 1967-07-11 Allied Chem Preparation of pyrosulfuryl fluoride and by-products
US3415607A (en) * 1965-03-01 1968-12-10 Warner Lambert Pharmaceutical Hair dye composition containing 2-hydroxy-1,4-naphthoquinone
DE3207036A1 (en) * 1981-02-27 1982-09-16 Oreal Hair dyes containing hydroxyanthrachinonverbindungen and a process for dyeing of human hair
US4602913A (en) * 1981-02-27 1986-07-29 L'oreal Use of hydroxyanthraquinones for the coloration of human keratin fibres
FR2517200A1 (en) * 1981-12-02 1983-06-03 Oreal
US4888026A (en) * 1981-12-02 1989-12-19 L'oreal Use of hydroxynaphthoquinones for dyeing human keratin fibres
US4867751A (en) * 1981-12-02 1989-09-19 L'oreal Use of benzoquinones for the direct dyeing of keratin fibres
US5259849A (en) * 1982-04-29 1993-11-09 L'oreal Composition based on quinone dyestuffs for use in hair dyeing and process for the preservation of quinone dyestuffs
US4895575A (en) * 1982-12-08 1990-01-23 L'oreal Use of 5-hydroxynaphthoquinones for dyeing human keratin fibres
US4605419A (en) * 1984-04-20 1986-08-12 Shiseido Company Ltd. 5,8-dihydroxy naphthalene-1,4-dione derivative and a hair dye composition containing the same
FR2563215A1 (en) * 1984-04-20 1985-10-25 Shiseido Co Ltd Derived from naphthalene and composition of hair dye containing
EP0257399A3 (en) * 1986-08-13 1988-04-20 Blendax-Werke R. Schneider Gmbh & Co. Hair dyeing composition
EP0257399A2 (en) * 1986-08-13 1988-03-02 Beratungslabor für die kosmetische und pharmazeutische Industrie Dipl.-Ing. Karlheinz Schrader Hair dyeing composition
US5785961A (en) * 1995-03-28 1998-07-28 Shiseido Company, Ltd. Mixing-at the time of use-type hair-treating composition
WO2002102336A1 (en) * 2001-06-19 2002-12-27 Wella Aktiengesellschaft Agent containing quinonimine derivatives and used to colour keratin fibres, and associated method
US20030182736A1 (en) * 2001-06-19 2003-10-02 Cecile Pasquier Agent containing quinonimine derivatives and used to colour keratin fibres, and associated method
US7056349B2 (en) 2001-06-19 2006-06-06 Wella Ag Agent containing quinonimine derivatives and used to color keratin fibres, and associated method
EP1982691A1 (en) * 2007-04-20 2008-10-22 KPSS-Kao Professional Salon Services GmbH Composition for coloring keratin fibres
EP2002821A1 (en) * 2007-04-20 2008-12-17 KPSS-Kao Professional Salon Services GmbH Composition for colouring keratin fibres

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