US3531502A - Anthraquinone dyes - Google Patents
Anthraquinone dyes Download PDFInfo
- Publication number
- US3531502A US3531502A US428867A US3531502DA US3531502A US 3531502 A US3531502 A US 3531502A US 428867 A US428867 A US 428867A US 3531502D A US3531502D A US 3531502DA US 3531502 A US3531502 A US 3531502A
- Authority
- US
- United States
- Prior art keywords
- hair
- hydroxy
- methyl
- aminoanthraquinone
- sulphate
- 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
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
- A61K8/355—Quinones
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/501—Amino-hydroxy-anthraquinones; Ethers and esters thereof containing onium groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/514—N-aryl derivatives
- C09B1/5145—N-aryl derivatives only amino and hydroxy groups
Definitions
- R is a lower alkyl radical (for instance a methyl, ethyl, propyl or butyl radical); and A- is an anion, such as a halogen or a methylsulphate ion.
- Examples of two compounds falling within the scope of the above-indicated Formula I are: bis-methyl-[lhydroxy 2,4 (p-trimethylammoniumphenyl)aminoanthraquinone]sulphate, that is the compound of Formula I where R is methyl and A" is methylsulphate, and [1- hydroxy-2,4 (p trimethyl-ammoniumphenyl) aminoanthraquinone] iodide, that is the compound of Formula I where R is methyl and A- is iodide.
- the quaternary salts of this invention when applied to the hair give attractive grey shades of great intensity for which there is need in the art of hair-dyeing. They also have the advantage that they are very soluble in water over a very wide pH range, the aqueous solutions obtained being, in general, tolerant of all the practical conditions under which hair dyeing is carried out. Moreover, the quaternary salts when applied to hair have a 3,531 ,502 Patented Sept. 29, 1970 high resistance to sunlight, which is a most valuable property for hair dyes, and they also well withstand the presence of ingredients generally incorporated in dyeing compositions, such as hair penetrating and swelling agents, lustre-producing products and thickening agents.
- 1 hydroxy 2,4 (p-dimethylaminophenyl) aminoanthraquinone can be obtained by the reaction of N,N-dimethyl-p-phenylenediamine with purpurin, that is, 1,2,4- trihydroxyanthraquinone.
- the quaternary salts of l-hydroxy 2,4 (p dimethylaminophenyl)aminoanthra quinone can be obtained by reacting the latter compound with a quaternising agent such as methyl iodide or methyl sulphate.
- the present invention also relates to a method of dyeing keratinic fibres, more particularly hair, by applying to the fibres a quaternary salt of this invention, allowing sufficient time to elapse for the said compound to exert its dyeing effect and then removing any unwanted excess of the compound from the hair.
- the quaternary salt is conveniently used in the form of an aqueous solution that is left in contact with the hair for about 15 to 60 minutes at ambient temperature, after which the hair is rinsed and washed.
- the invention also comprises dyeing compositions suitable for dyeing keratinic fibres, which may take the form of solutions, emulsions, gels or creams, containing a quaternary salt of this invention.
- the dyeing composi tions preferably have a pH value of from 3 to 9.
- the dye compositions of the" invention may be used in combination with other dyestufis which may or may not be quaternary salts of this invention or belong to the family of the anthraquinone dyestuffs.
- a dyeing solution according to the invention is prepared by mixing:
- This solution is applied to 100% white hair and left in contact therewith for 20 minutes at ambient temperature, whereafter the hair is washed, rinsed and dried.
- the coloration thus obtained in the hair is violet-grey.
- a dyeing solution according to the invention is prepared by mixing: 1-hydroXy-2,4- (p-trimethylammoniumphenyl) arninoanthraquinone] iodide-10 g. Sodium carbonate, q.s. for pH 7 Water, q.s. for 1000 cc.
- This solution is applied to 100% white hair and left in contact therewith for 20 minutes at ambient temperature, whereafter the hair is rinsed, shampooed, rinsed again and dried.
- the coloration thus obtained in the hair is blue-grey.
- a dyeing solution according to the invention is prepared by mixing:
- N-monomethylnitro-p-phenylenediamine 6.5 l-(v-dimethylaminopropyl)-amino, 2-amino-4- nitrobenzene monohydrochloride 12
- Sodium carbonate q.s. for pH 8.5. Water, q.s. for 1000 cc.
- R is a lower alkyl having 1-4 carbon atoms and A* is a halide or methyl sulfate.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Chemistry (AREA)
- Emergency Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR962659A FR1430091A (fr) | 1964-02-05 | 1964-02-05 | Nouveaux colorants anthraquinoniques et nouveaux procédés de teinture des cheveux à l'aide de ces colorants |
Publications (1)
Publication Number | Publication Date |
---|---|
US3531502A true US3531502A (en) | 1970-09-29 |
Family
ID=8822443
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US428867A Expired - Lifetime US3531502A (en) | 1964-02-05 | 1965-01-28 | Anthraquinone dyes |
US37903A Expired - Lifetime US3692461A (en) | 1964-02-05 | 1970-05-15 | Hair dye composition and method of dyeing human hair therewith |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US37903A Expired - Lifetime US3692461A (en) | 1964-02-05 | 1970-05-15 | Hair dye composition and method of dyeing human hair therewith |
Country Status (8)
Country | Link |
---|---|
US (2) | US3531502A (xx) |
AT (2) | AT269359B (xx) |
BE (1) | BE659168A (xx) |
CH (2) | CH435507A (xx) |
DE (1) | DE1492073A1 (xx) |
FR (1) | FR1430091A (xx) |
GB (1) | GB1050863A (xx) |
NL (2) | NL6501324A (xx) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5314505A (en) * | 1991-11-01 | 1994-05-24 | Clairol, Inc. | Aminoan thraquinone dyes having a quaternary center with a long aliphatic chain |
US20050011012A1 (en) * | 2003-03-19 | 2005-01-20 | Regents Of The University Of California | Multifunctional antimicrobial dyes |
WO2007090800A2 (en) * | 2006-02-09 | 2007-08-16 | Dystar Textilfarben Gmbh & Co Deutschland Kg | Hair dye compositions |
US20080201871A1 (en) * | 2003-03-19 | 2008-08-28 | The Regents Of The University Of California | Antimicrobial colorants |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4138415A (en) * | 1978-05-05 | 1979-02-06 | American Cyanamid Company | 1,4-Bis(aminoalkylamino)-anthraquinones and leuco derivatives thereof |
LU83177A1 (fr) * | 1981-02-27 | 1982-09-10 | Oreal | Utilisation d'hydroxyanthraquinones pour la coloration des fibres keratiniques humaines,procede et composition les mettant en oeuvre |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1937531A (en) * | 1928-06-22 | 1933-12-05 | Nat Aniline & Chem Co Inc | Production of anthraquinone dyestuffs |
US3004974A (en) * | 1958-12-24 | 1961-10-17 | Ciba Ltd | Water-soluble salts of anthraquinone dyestuffs |
US3192117A (en) * | 1961-02-23 | 1965-06-29 | Therachemie Chem Therapeut | Hair dye comprising substituted anthraquinones in shampoo base |
US3368942A (en) * | 1963-09-04 | 1968-02-13 | Therachemie Chem Therapeut | Water soluble aminoanthraquinone hair dyes |
-
0
- GB GB1050863D patent/GB1050863A/en active Active
- NL NL125671D patent/NL125671C/xx active
-
1964
- 1964-02-05 FR FR962659A patent/FR1430091A/fr not_active Expired
-
1965
- 1965-01-28 CH CH154867A patent/CH435507A/fr unknown
- 1965-01-28 CH CH119865A patent/CH440558A/fr unknown
- 1965-01-28 US US428867A patent/US3531502A/en not_active Expired - Lifetime
- 1965-01-30 DE DE19651492073 patent/DE1492073A1/de not_active Withdrawn
- 1965-02-02 NL NL6501324A patent/NL6501324A/xx unknown
- 1965-02-02 BE BE659168D patent/BE659168A/xx unknown
- 1965-02-02 AT AT868065A patent/AT269359B/de active
- 1965-02-02 AT AT90865A patent/AT251145B/de active
-
1970
- 1970-05-15 US US37903A patent/US3692461A/en not_active Expired - Lifetime
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1937531A (en) * | 1928-06-22 | 1933-12-05 | Nat Aniline & Chem Co Inc | Production of anthraquinone dyestuffs |
US3004974A (en) * | 1958-12-24 | 1961-10-17 | Ciba Ltd | Water-soluble salts of anthraquinone dyestuffs |
US3192117A (en) * | 1961-02-23 | 1965-06-29 | Therachemie Chem Therapeut | Hair dye comprising substituted anthraquinones in shampoo base |
US3368942A (en) * | 1963-09-04 | 1968-02-13 | Therachemie Chem Therapeut | Water soluble aminoanthraquinone hair dyes |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5314505A (en) * | 1991-11-01 | 1994-05-24 | Clairol, Inc. | Aminoan thraquinone dyes having a quaternary center with a long aliphatic chain |
US20050011012A1 (en) * | 2003-03-19 | 2005-01-20 | Regents Of The University Of California | Multifunctional antimicrobial dyes |
US20080201871A1 (en) * | 2003-03-19 | 2008-08-28 | The Regents Of The University Of California | Antimicrobial colorants |
WO2007090800A2 (en) * | 2006-02-09 | 2007-08-16 | Dystar Textilfarben Gmbh & Co Deutschland Kg | Hair dye compositions |
WO2007090799A2 (en) | 2006-02-09 | 2007-08-16 | Dystar Textilfarben Gmbh & Co Deutschland Kg | Dyestuffs and hair dye compositions |
EP1820826A1 (en) * | 2006-02-09 | 2007-08-22 | DyStar Textilfarben GmbH & Co. Deutschland KG | Dyestuffs and Hair Dye Compositions |
WO2007090800A3 (en) * | 2006-02-09 | 2007-12-21 | Dystar Textilfarben Gmbh & Co | Hair dye compositions |
WO2007090799A3 (en) * | 2006-02-09 | 2008-01-10 | Dystar Textilfarben Gmbh & Co | Dyestuffs and hair dye compositions |
US20090217466A1 (en) * | 2006-02-09 | 2009-09-03 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Dyestuffs and hair dye compositions |
US20090249564A1 (en) * | 2006-02-09 | 2009-10-08 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Hair dye compositions |
US7776106B2 (en) | 2006-02-09 | 2010-08-17 | Dystar Textilfarben Gmbh & Co., Deutschland Kg | Dyestuffs and hair dye compositions |
Also Published As
Publication number | Publication date |
---|---|
US3692461A (en) | 1972-09-19 |
CH440558A (fr) | 1967-07-31 |
GB1050863A (xx) | |
AT251145B (de) | 1966-12-12 |
FR1430091A (fr) | 1966-03-04 |
NL125671C (xx) | |
NL6501324A (xx) | 1965-08-06 |
AT269359B (de) | 1969-03-10 |
DE1492073A1 (de) | 1969-05-14 |
CH435507A (fr) | 1967-05-15 |
BE659168A (xx) | 1965-08-02 |
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