US3402986A - Dyeing live human hair with direct dyes and alcohol solvents - Google Patents
Dyeing live human hair with direct dyes and alcohol solvents Download PDFInfo
- Publication number
- US3402986A US3402986A US533239A US53323966A US3402986A US 3402986 A US3402986 A US 3402986A US 533239 A US533239 A US 533239A US 53323966 A US53323966 A US 53323966A US 3402986 A US3402986 A US 3402986A
- Authority
- US
- United States
- Prior art keywords
- hair
- alcohol
- dyeing
- human hair
- live human
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 210000004209 hair Anatomy 0.000 title description 25
- 239000000982 direct dye Substances 0.000 title description 16
- 238000004043 dyeing Methods 0.000 title description 16
- 239000005456 alcohol based solvent Substances 0.000 title description 2
- 239000000203 mixture Substances 0.000 description 14
- 239000000975 dye Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- -1 thioether alcohols Chemical class 0.000 description 10
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 8
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- MEBQXILRKZHVCX-UHFFFAOYSA-N methidathion Chemical compound COC1=NN(CSP(=S)(OC)OC)C(=O)S1 MEBQXILRKZHVCX-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000012736 aqueous medium Substances 0.000 description 5
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 235000014655 lactic acid Nutrition 0.000 description 4
- 239000004310 lactic acid Substances 0.000 description 4
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 3
- 229950006389 thiodiglycol Drugs 0.000 description 3
- 229930194542 Keto Natural products 0.000 description 2
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 239000000981 basic dye Substances 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
-
- 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
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
-
- 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
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
- A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/42—Colour properties
- A61K2800/43—Pigments; Dyes
- A61K2800/432—Direct dyes
-
- Y—GENERAL 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/917—Wool or silk
Definitions
- ABSTRACT OF THE DISCLOSURE Method of dyeing hair at ambient temperature using a direct dye dispersed in an aqueous medium containing not more than 10% by weight of any water miscible alcohol selected from the group consisting of thioether alcohols, keto alcohols, saturated carbocyclic alcohols and heterocyclic alcohols that are colorless, non-toxic and chemically indifferent to the dye and hair.
- any water miscible alcohol selected from the group consisting of thioether alcohols, keto alcohols, saturated carbocyclic alcohols and heterocyclic alcohols that are colorless, non-toxic and chemically indifferent to the dye and hair.
- This invention relates to compositions which can be used for dyeing animal fibres, particularly for dyeing live human hair and to the preparation and use of such compositions.
- composition for dyeing live human hair comprising a solution of a direct dye in an aqueous organic solvent which is chemically indifferent with respect to the dye and to the product to be dyed, the said solvent being completely miscible with water in the proportion in which it is present and having the general formula:
- R represents an aliphatic hydrocarbon group having a straight or branched chain containing at most 8 carbon atoms
- n is from 1 to 4.
- direct dye any dyestuff capable of being fixed directly and in the final shade by the hair to be dyed, without it being necessary to interpose any chemical transformation, such as for example an oxidation, a coupling or a mordanting of the fibre.
- organic solvents miscible to greater or lesser degree with water which are employed in the present invention act in the same manner as those of the aforesaid patent by considerably increasing the developments and the fixing of such dyestuffs on the hair, either at ambient temperature or under the aforesaid temperature conditions.
- a composition for dyeing animal fibres and human hair comprises a solution of a direct dye in an aqueous alcohol which is chemically indifferent with respect to the dye and to the hair, the said alcohol being miscible with water in the proportion in which it is present and being selected from the class consisting of butyl alcohol, thioether alcohols, keto alcohols, aralkanols, carbocyclic alcohols and heterocyclic alcohols and mixtures thereof.
- thioether alcohol e.g., thiodiglycol (up to 10%);
- ketoalcohol e.g., diacetone alcohol (up to 10%);
- an aralkanol e.g. benzyl alcohol (up to 4%) or betaphenylethyl alcohol (up to 1%);
- a carbocyclic alcohol e.g. cyclohexanol (up to 3%);
- a heterocyclic alcohol e.g. furfuryl alcohol.
- nitro such as methylisopicramic acid and l-hydroxy-Z-amino- S-nitrobenzene, azo, anthraquinone, pigment, basic dyes complex metalliferous dyes, examples of which are given hereinafter.
- compositions of the invention contain a small proportion of an organic acid, e.g., lactic acid.
- the dyes used are of the aforesaid types, having very low affinity, or even no affinity, for hair at ambient temperature under the conditions of application previously
- This solution is applied at ambient temperature to live hair which is naturally white and it is left in contact therewith for 15-20 minutes, whereupon the hair is rinsed with clean Water.
- a deep grey shade is obtained with yellow tints.
- Supracide Black is the following composition, as described in British Patent 758,743:
- S OaNa Supracide Brown 4R has the following structure, as described in British Patent 758,743:
- the dye compositions of this invention may contain conventional adjuvants, such as foaming agents, softeners and other products intended to brighten or improve in any other manner the texture or appearance of the hair.
- a method of dyeing live human hair with a direct dye comprising applying a direct dye composition to the hair at ambient temperatures, said composition comprising a direct dye distributed in a substantially aqueous medium having an amount, not exceeding about 10% of the total weight thereof, of an alcohol which is totally miscible in water in the proportions added and is selected from the group consisting of thiodiglycol, diacetone alcohol, cyclohexanol, furfuryl alcohol and mixtures thereof.
- a method of dyeing live human hair with direct dye stuff comprising dyeing the hair at ambient temperature with a composition comprising a direct dye distributed in a substantially aqueous medium containing an amount not exceeding about 10% of the total thereof, of diacetone alcohol.
- a method of dyeing live human hair with a direct dye stuff comprising dyeing the hair at ambient temperature with a composition comprising a direct dye distributed in a substantially aqueous medium containing an amount, not exceeding about 10% of the total thereof, of thiodiglycol.
- a method of dyeing live human hair with a direct dye stuff comprising dyeing the hair at ambient temperature with a composition comprising a direct dye stuff distributed in a substantially aqueous medium containing an amount, not exceeding about 10% of the total thereof, of furfuryl alcohol.
Landscapes
- 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)
- Emergency Medicine (AREA)
- Cosmetics (AREA)
- Coloring (AREA)
Description
United States Patent 3,402,986 DYEING LIVE HUMAN HAIR WITH DIRECT DYES AND ALCOHOL SOLVENTS Charles Zviak, La Garenne, and Giuliana Ghilardi, Paris,
France, assignors to Societe Anonyme dit: Societe Monsavon lOreal, Paris, France, a corporation of France No Drawing. Continuation of application Ser. No.
689,267, Oct. 10, 1957. This application Mar. 10,
1966, Ser. No. 533,239 7 Claims. (Cl. 8--10.1)
ABSTRACT OF THE DISCLOSURE Method of dyeing hair at ambient temperature using a direct dye dispersed in an aqueous medium containing not more than 10% by weight of any water miscible alcohol selected from the group consisting of thioether alcohols, keto alcohols, saturated carbocyclic alcohols and heterocyclic alcohols that are colorless, non-toxic and chemically indifferent to the dye and hair.
This application is a continuation of our prior application Ser. No. 689,267, filed Oct. 10, 1957, and now abandoned.
This invention relates to compositions which can be used for dyeing animal fibres, particularly for dyeing live human hair and to the preparation and use of such compositions.
In copending US. Patent No. 2,983,651, there is described a composition for dyeing live human hair comprising a solution of a direct dye in an aqueous organic solvent which is chemically indifferent with respect to the dye and to the product to be dyed, the said solvent being completely miscible with water in the proportion in which it is present and having the general formula:
in which R represents an aliphatic hydrocarbon group having a straight or branched chain containing at most 8 carbon atoms, n is from 1 to 4. By direct dye is meant any dyestuff capable of being fixed directly and in the final shade by the hair to be dyed, without it being necessary to interpose any chemical transformation, such as for example an oxidation, a coupling or a mordanting of the fibre.
It has now been found that other organic solvents miscible to greater or lesser degree with water and of a constitution different from those of the general formula given in the aforesaid patent permit similar results to be obtained, i.e., permit the use of a large number of dyestuffs which normally, under temperature conditions lower than C., have only a very low aflinity, or even no affinity, for hair and which have so far been considered unsuitable for practical use for such an application.
The organic solvents miscible to greater or lesser degree with water, which are employed in the present invention act in the same manner as those of the aforesaid patent by considerably increasing the developments and the fixing of such dyestuffs on the hair, either at ambient temperature or under the aforesaid temperature conditions.
According to the present invention a composition for dyeing animal fibres and human hair comprises a solution of a direct dye in an aqueous alcohol which is chemically indifferent with respect to the dye and to the hair, the said alcohol being miscible with water in the proportion in which it is present and being selected from the class consisting of butyl alcohol, thioether alcohols, keto alcohols, aralkanols, carbocyclic alcohols and heterocyclic alcohols and mixtures thereof.
Illustrative examples of such alcohols and preferred weight proportions in which they are used are:
(l) butyl alcohol (up to 5%);
(2) a thioether alcohol, e.g., thiodiglycol (up to 10%);
(3) a ketoalcohol, e.g., diacetone alcohol (up to 10%);
(4) an aralkanol, e.g. benzyl alcohol (up to 4%) or betaphenylethyl alcohol (up to 1%);
(5) a carbocyclic alcohol, e.g. cyclohexanol (up to 3%);
(6) a heterocyclic alcohol, e.g. furfuryl alcohol.
It will be understood that the proportions are only given by way of example. They can be increased or reduced according to the effect which is desired without thereby departing from the scope of the invention, provided that the limits of miscibility of the selected solvents and of the water are maintained. Moreover, in the case where two or more solvents corresponding to the aforesaid compounds are associated, the percentages given by way of indication in the case where one of the solvents is used must generally be reduced. Finally, it is possible for one of the solvents listed above or several of such solvents to have mixed therewith one or more other solvents corresponding to the aforesaid formula:
where R and n have the value set forth above, the respective proportions being modified in consequence.
Among the direct dyes (as hereinabove defined) suitable for use according to the present invent-ion are: nitro, such as methylisopicramic acid and l-hydroxy-Z-amino- S-nitrobenzene, azo, anthraquinone, pigment, basic dyes complex metalliferous dyes, examples of which are given hereinafter.
Preferably the compositions of the invention contain a small proportion of an organic acid, e.g., lactic acid.
The following examples will serve to illustrate the invention: the dyes used are of the aforesaid types, having very low affinity, or even no affinity, for hair at ambient temperature under the conditions of application previously This solution is applied at ambient temperature to live hair which is naturally white and it is left in contact therewith for 15-20 minutes, whereupon the hair is rinsed with clean Water. A deep grey shade is obtained with yellow tints.
Example H The following solution is prepared:
Percent Supracide Brown 4R 3 Diacetone alcohol 10 Lactic acid 3 Water to make A beige shade with slightly pink tints is obtained by operating as indicated in Example I.
Example HI The following solution is prepared:
Percent Supracide Brown 4R 3 Benzyl alcohol a 3 Lactic acid 3 Water to make 100 Patented Sept. 24, 1968" A deep brown shade with pink tints is obtained when I operating'as indicated in Example 1.
Example IV The following solution is prepared:
Percent Supracide Black 1 Beta-phenylethyl alcohol l Lactic acid 3 Water to make 100 A grey shade is obtained by operating at indicated in Example I.
A beautiful beige shade with pink tints is obtained by operating as indicated in Example I.
Example VI The following solution is prepared:
Percent Supracide Black 1 2-butoxyethanol 7 Benzyl alcohol 3 Lactic acid 3 Water to make 100 A very deep grey is obtained when operating as indicated in Example I.
Supracide Black is the following composition, as described in British Patent 758,743:
S OaNa Supracide Brown 4R has the following structure, as described in British Patent 758,743:
iNEi The majority of the dyes set forth above as dyes suitable for carrying the present invention into effect, are dyes which are proposed especially by the manufacturers for dyeing cellulose acetate, cotton and other cellulose fibres. It is thus all the more surprising that it is possible by using such dyes in accordance with the present invention to obtain a very satisfactory dyeing of keratinic fibres such as wool and hair, this even being possible at ambient temperature.
Furthermore, it will be understood that it is possible for two or more of these dyes to be associated in a single dye solution in identical or different proportions in order to obtain any desired shade and more particularly to match a natural shade of hair.
The dye compositions of this invention may contain conventional adjuvants, such as foaming agents, softeners and other products intended to brighten or improve in any other manner the texture or appearance of the hair.
What is claimed is:
1. A method of dyeing live human hair with a direct dye comprising applying a direct dye composition to the hair at ambient temperatures, said composition comprising a direct dye distributed in a substantially aqueous medium having an amount, not exceeding about 10% of the total weight thereof, of an alcohol which is totally miscible in water in the proportions added and is selected from the group consisting of thiodiglycol, diacetone alcohol, cyclohexanol, furfuryl alcohol and mixtures thereof.
2. The method of claim 1, wher in said alcohol is cyclohexanol.
3. A method of dyeing live human hair with direct dye stuff comprising dyeing the hair at ambient temperature with a composition comprising a direct dye distributed in a substantially aqueous medium containing an amount not exceeding about 10% of the total thereof, of diacetone alcohol.
4. A method of dyeing live human hair with a direct dye stuff comprising dyeing the hair at ambient temperature with a composition comprising a direct dye distributed in a substantially aqueous medium containing an amount, not exceeding about 10% of the total thereof, of thiodiglycol.
5. A method of dyeing live human hair with a direct dye stuff comprising dyeing the hair at ambient temperature with a composition comprising a direct dye stuff distributed in a substantially aqueous medium containing an amount, not exceeding about 10% of the total thereof, of furfuryl alcohol.
References Cited FOREIGN PATENTS 758,743 10/1956 Great Britain.
ALBERT T. MEYERS, Primary Examiner, Y. CLARKE, Assistant Examiner.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US533239A US3402986A (en) | 1966-03-10 | 1966-03-10 | Dyeing live human hair with direct dyes and alcohol solvents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US533239A US3402986A (en) | 1966-03-10 | 1966-03-10 | Dyeing live human hair with direct dyes and alcohol solvents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3402986A true US3402986A (en) | 1968-09-24 |
Family
ID=24125102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US533239A Expired - Lifetime US3402986A (en) | 1966-03-10 | 1966-03-10 | Dyeing live human hair with direct dyes and alcohol solvents |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3402986A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3617211A (en) * | 1969-07-08 | 1971-11-02 | Allied Chem | Phenyl glycol and short-chain halogenated hydrocarbon dye composition |
| US3981676A (en) * | 1970-03-03 | 1976-09-21 | L'oreal | Lyophilized dyes and the use thereof to color keratinic fibers |
| US3981678A (en) * | 1970-03-03 | 1976-09-21 | L'oreal | Lyophilized dyes and the use thereof to color keratinic fibers |
| US4145413A (en) * | 1977-08-15 | 1979-03-20 | The Gillette Company | Artificial skin darkening composition and method of using the same |
| US4873079A (en) * | 1987-08-21 | 1989-10-10 | Clairol Incorporated | Hair coloring composition and its method of use |
| US6440175B1 (en) * | 2001-06-28 | 2002-08-27 | Stanley, Iii Virgil E. | Hair coloring kit |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB758743A (en) * | 1953-01-19 | 1956-10-10 | Oreal | Improvements in or relating to the dyeing of human hair |
-
1966
- 1966-03-10 US US533239A patent/US3402986A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB758743A (en) * | 1953-01-19 | 1956-10-10 | Oreal | Improvements in or relating to the dyeing of human hair |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3617211A (en) * | 1969-07-08 | 1971-11-02 | Allied Chem | Phenyl glycol and short-chain halogenated hydrocarbon dye composition |
| US3981676A (en) * | 1970-03-03 | 1976-09-21 | L'oreal | Lyophilized dyes and the use thereof to color keratinic fibers |
| US3981678A (en) * | 1970-03-03 | 1976-09-21 | L'oreal | Lyophilized dyes and the use thereof to color keratinic fibers |
| US4145413A (en) * | 1977-08-15 | 1979-03-20 | The Gillette Company | Artificial skin darkening composition and method of using the same |
| US4873079A (en) * | 1987-08-21 | 1989-10-10 | Clairol Incorporated | Hair coloring composition and its method of use |
| US6440175B1 (en) * | 2001-06-28 | 2002-08-27 | Stanley, Iii Virgil E. | Hair coloring kit |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0007537B1 (en) | Hair dyeing composition | |
| EP0008039B1 (en) | Hair dyeing composition containing 6-amino-3-methyl-phenol | |
| DE69001413T2 (en) | A COLOR AGENT FOR KERATINE FIBERS AND METHOD CONTAINING AN INDOLE DYE AND AT LEAST ONE PARAPHENYLENE DIAMINE WITH A SECOND AMINO GROUP. | |
| JP2000503327A (en) | Dyeing agent that exhibits metameric effect on keratin fiber | |
| US4395262A (en) | Hair dyeing agent | |
| US3402986A (en) | Dyeing live human hair with direct dyes and alcohol solvents | |
| US3480377A (en) | Solvent dyeing of living human hair | |
| DE2509096A1 (en) | HAIR DYE PRODUCTS | |
| US2733186A (en) | Compositions for the dyeing of hair | |
| DE2702118B2 (en) | Hair dye | |
| US2695259A (en) | Dermatologically harmless hair dyeing creams | |
| DE2160317C3 (en) | Preparations for coloring human hair | |
| KR0129858B1 (en) | Hair dye | |
| EP0132568B1 (en) | Derivatives of 1,4-diamino-5-chloro-2-nitrobenzene, process for their production and agents for dyeing hair | |
| NO167437C (en) | APPLICATION OF NITROBENZEN DERIVATIVES AS DIRECT PURCHASING HAIR COLORS | |
| EP0002828B1 (en) | Hair dyeing composition | |
| US3011858A (en) | Process for dyeing hair, fur and other keratinic fibers with dihydroxyaminobenzenes | |
| US3128232A (en) | Oxidation dyestuff agent for human hair | |
| US3989447A (en) | Process for nonpermanently dyeing human hair with indamine indoaniline and indophenol hair dyes | |
| US3206363A (en) | Composition and process for solvent dyeing with tetraloweralkyl ureas | |
| EP0150765B1 (en) | Use of p-ureidoalkylamino nitrobenzene compounds in hair dyeing compositions and p-ureidoalkylamino nitrobenzene compounds | |
| EP0881894B1 (en) | Dyeing agent for dyeing keratin fibres | |
| US3619102A (en) | Dyeing keratinic fibers with aqueous solutions of direct dyes and organic solvents | |
| US2338745A (en) | Dyeing of hair | |
| US3251744A (en) | Naphthazarin hair dyeing composition and method |