GB1097271A - Naphthoquinone imine dyestuffs, and hair dyeing compositions - Google Patents
Naphthoquinone imine dyestuffs, and hair dyeing compositionsInfo
- Publication number
- GB1097271A GB1097271A GB64165A GB64165A GB1097271A GB 1097271 A GB1097271 A GB 1097271A GB 64165 A GB64165 A GB 64165A GB 64165 A GB64165 A GB 64165A GB 1097271 A GB1097271 A GB 1097271A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- hydrogen
- alkyl
- formula
- naphthoquinone
- 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
Links
Classifications
-
- 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
- A61K8/413—Indoanilines; Indophenol; Indoamines
-
- 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
Landscapes
- 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)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises naphthoquinone imines (I) having the formula <FORM:1097271/C4-C5/1> and tautomers thereof, wherein n is 1-3, which are obtained by condensing 5,8-dihydroxy-1,4-naphtho quinone with the appropriate alkylene polyamine and (2) having the formula <FORM:1097271/C4-C5/2> and tautomers thereof wherein R represents a hydroxyalkyl aminoalkyl radical or a phenyl radical bearing an amino group -NR1R2 wherein either R1 is alkyl and R2 is hydrogen or alkyl or R1 and R2 are hydrogen or monoor poly-hydroxyalkyl, at most one of R1 and R2 being hydrogen, the formula <FORM:1097271/C4-C5/3> and tautomers thereof wherein R1 is -alkylene-or -(alkylene-NH)n-alkylene-, n being 1 to 3, or the formula <FORM:1097271/C4-C5/4> and tautomers thereof, wherein X is a monovalent radical R or a divalent radical -R1-or -R1-R1-, r being 1 or 2 according to the valency of X and R and R1 are the heterocyclic groups; 2-pyridyl, 3-pyridyl, 6-amino-2-pyridyl, 2 - methyl - 4 - thiazodyl, 4 - quinolyl, 7-quinolyl, 2 - imidazolyl, 5 - benzimidazolyl, 2-benthiazolyl or 2-naphtho-(1,2)-thiazolyl. The imines of (2) and other analogous naphthoquinone imines are prepared by condensing a primary mono- or di-amine with 5-amino-8-hydroxy - 1,4 - naphthoquinone - 1 - imine (NI); condensation of the di-amine with two moles of NI yield a bis-naphthoquinone imine. Numerous examples are given of the condensation of NI with primary alkyl amines, N-hydroxyethyl ethylene diamine, polyhydroxy alkyl amines, alkylene polyamines, hydroxy and alkoxy aromatic amines, hydroxy alkyl phenylene diamines, dialkylamino aromatic amines, nitro anilines, amino benzyl alcohols, and heterocyclic amines. NI is prepared by reacting 1,5-dinitro naphthalene with sulphuric acid and purified by heating it in an aqueous solution of a secondary or tertiary alkanolamine followed by precipitation with brine. The NI may be sulphonated by adding the imine in powder form to oleum at 25-30 DEG C. The various imines and others of the general formula <FORM:1097271/C4-C5/5> and tautomers thereof wherein X is a monovalent radical -R or a divalent radical -R1-, wherein R is hydrogen or a monovalent aliphatic, cycloaliphatic, aryl, aralkyl or heterocyclic radical and R1 is a divalent aliphatic, cycloaliphatic, arylene, aralkyl or heterocyclic radical, r is 1 or 2 depending on X and A, B, C, D, E and G are hydrogen, chlorine, bromine, sulpho, alkyl or -HNR, where R is as defined above and wherein A and B may also be hydroxy, may be used for hair dyeing (see Division D1).ALSO:Human hair is dyed on the head with a substantive naphthoquinone imine represented by the formula <FORM:1097271/D1-D2/1> wherein X is a monovalent radical -R or divalent radical -R\svwherein R is hydrogen or a monovalent aliphatic, cycloaliphatic, aryl, aralkyl or heterocyclic radical and R\sv is a divalent aliphatic, cycloaliphatic, arylene, aralkyl or heterocyclic radical, r is 1 or 2 depending on the value of X and A, B, C, D, E and G are hydrogen, chlorine, bromine, sulpho, alkyl or -HNR where R is as above defined and wherein A and B may also be hydroxy. The dyes may be used in aqueous media which are acid or alkaline, alone or with other direct dyes and/or with oxidation dyes, including nitro, azo, phenolic and anthraquinone dyes and phenylene diamines. The oxidation dyes are used in conjunction with H2O2 or urea peroxide. The dyes may be used together with conventional anionic, cationic or non-ionic surfactants and with thickening agents. Numerous examples are given.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US34510764A | 1964-02-17 | 1964-02-17 | |
US37383864A | 1964-06-09 | 1964-06-09 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1097271A true GB1097271A (en) | 1968-01-03 |
Family
ID=26994257
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB64165A Expired GB1097271A (en) | 1964-02-17 | 1965-01-06 | Naphthoquinone imine dyestuffs, and hair dyeing compositions |
Country Status (5)
Country | Link |
---|---|
CH (1) | CH480838A (en) |
DE (1) | DE1467837A1 (en) |
FR (1) | FR1555464A (en) |
GB (1) | GB1097271A (en) |
SE (1) | SE328090B (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL7008472A (en) * | 1969-06-11 | 1970-12-15 | ||
FR2111698A1 (en) * | 1970-10-19 | 1972-06-09 | Oreal | |
NL7110684A (en) * | 1970-12-11 | 1972-06-13 | ||
NL7112460A (en) * | 1970-12-21 | 1972-06-23 | ||
NL7708063A (en) * | 1976-07-21 | 1978-01-24 | Oreal | PROCESS FOR PREPARING A SOLUTION OF ONE OR MORE COLOR AGENTS FOR DYING HAIR. |
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 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
LU59063A1 (en) * | 1969-07-08 | 1971-03-09 | ||
JP2001288054A (en) * | 2000-04-07 | 2001-10-16 | Kao Corp | Hair dye |
-
1965
- 1965-01-05 CH CH6065A patent/CH480838A/en not_active IP Right Cessation
- 1965-01-05 FR FR1555464D patent/FR1555464A/fr not_active Expired
- 1965-01-06 GB GB64165A patent/GB1097271A/en not_active Expired
- 1965-01-08 DE DE19651467837 patent/DE1467837A1/en active Pending
- 1965-01-08 SE SE16565A patent/SE328090B/xx unknown
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL7008472A (en) * | 1969-06-11 | 1970-12-15 | ||
FR2111698A1 (en) * | 1970-10-19 | 1972-06-09 | Oreal | |
NL7110684A (en) * | 1970-12-11 | 1972-06-13 | ||
NL7112460A (en) * | 1970-12-21 | 1972-06-23 | ||
NL7708063A (en) * | 1976-07-21 | 1978-01-24 | Oreal | PROCESS FOR PREPARING A SOLUTION OF ONE OR MORE COLOR AGENTS FOR DYING HAIR. |
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 |
Also Published As
Publication number | Publication date |
---|---|
DE1467837A1 (en) | 1968-12-12 |
FR1555464A (en) | 1969-01-31 |
SE328090B (en) | 1970-09-07 |
CH480838A (en) | 1969-11-15 |
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