GB951667A - New water soluble azo dyestuffs containing quaternary ammonium groups - Google Patents
New water soluble azo dyestuffs containing quaternary ammonium groupsInfo
- Publication number
- GB951667A GB951667A GB1469561A GB1469561A GB951667A GB 951667 A GB951667 A GB 951667A GB 1469561 A GB1469561 A GB 1469561A GB 1469561 A GB1469561 A GB 1469561A GB 951667 A GB951667 A GB 951667A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloride
- radical
- ethyl
- phenyl
- product
- 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
-
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/085—Monoazo 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
- C09B44/00—Azo dyes containing onium groups
- C09B44/02—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
p-(b -N-ethyl-phenylaminoethoxy) - phenyl trimethylammonium chloride is obtained by reacting N-ethylaniline with p-nitrophenoxyethyl bromide, catalytically reducing the product with hydrogen, treating the product with dimethyl sulphate and then sodium hydroxide and acidifying the mixture with hydrochloric acid. 3-(41-aminobenzoylamino) phenyl-trimethyl ammonium chloride is obtained by reacting p-nitrobenzoyl chloride with m-aminophenyltrimethyl ammonium bromide, isolating the product as chloride and reducing the nitrogroup catalytically. 3-(31-hydroxy-21-naphthoylamino) phenyl trimethyl ammonium chloride is obtained by condensing m-aminophenyl trimethyl ammonium bromide with 2-hydroxy-3-naphthoyl chloride, isolating the product and treating with hydrochloric acid. 3-(41-aminophenylsulphonylamino) phenyl trimethylammonium chloride is obtained by reacting m-aminophenyl trimethylammonium bromide with p-acetamidobenzene sulphonyl-chloride, hydrolysing the product with hydrochloric acid and isolating the desired chloride. 4-(41-dimethylaminobenzoylamino) phenol is obtained by phosgenating dimethyl aniline and condensing the product with p-aminophenol. N-ethyl-N-p-dimethylaminobenzoyloxyethyl aniline is obtained by condensing the intermediate from the last process with N-ethyl-N-b -hydroxyethylaniline in the presence of pyridine.ALSO:The invention comprises water-soluble dyes of the formula <FORM:0951667/C3/1> wherein D represents the residue of an azo dye devoid of sulphonic and carboxylic groups, A represents an arylene radical, X represents a bivalent non-chromophoric radical which links the arylene radical A to an aromatic ring of the residue D, R, R1 and R11 represent alkyl or substituted alkyl radicals and Z represents an anion and process for the preparation thereof comprising (a) coupling a diazo component with a coupling component, provided that both components are devoid of sulphuric and carboxylic acid groups and one of said components contains, attached to an aromatic ring, a radical of the formula <FORM:0951667/C3/2> or (b) treating a water-insoluble dyestuff of the formula <FORM:0951667/C3/3> with an alkylating agent. Values specified for X are as follows, the arylene ring being attached to the right-hand side of the divalent radical: -CO-, -SO2-, -OB-, -BO-, -SO2N(Q)-, -COO-, N(Q)B, -N(Q)BO, N(Q)BOCO-, -N(Q)BN(Q)CO-, -N(Q)CO- and <FORM:0951667/C3/4> where Q = hydrogen or a hydrocarbon radical optionally substituted, e.g. methyl, ethyl, b -hydroxyethyl, phenyl, p-tolyl, B = an alkylene radical, e.g. -CH2, -CH2CH2-, -CH2CH2-CH2-, Y = chlorine or bromine, a hydroxyl or amino radical or an organic radical containing O, N or S attached to the triazine ring, e.g. a methoxy, phenoxy, p-tolylthio-, phenylamino or 4-dimethylaminophenylamino radical. A may be o-, m- or p-phenylene or 1 : 4, 1 : 5 or 1 : 7-naphthylene. R, R1 and R11 may be methyl, ethyl or b -hydroxyethyl. Z may be a chloride, iodide, sulphate, methosulphate, methyl- or p-tolylsulphonate ion. Among the dyes described are 4 - aminophenylmethyl sulphone --> p-(b - N - ethyl - N - phenylamino - ethoxy) phenyltrimethylammonium chloride, 3 - (41-aminobenzoyloxy) - N : N - diethylaniline --> 1 - phenyl - 3 - methyl - 5 - pyrazolone and 2-chloro - 4 - nitroaniline --> 2 : 4 - di - (41-dimethylaminophenylamino) - 6 - [b - N - phenylamino - ethylamino] - 1 : 3 : 5 - triazine quaternated with dimethyl sulphate in the presence of magnesium oxide and boiling monochlorbenzene. The dyes are particularly suitable for colouring textile materials of polymers and copolymers of acrylonitrile and dicyanoethylene.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1469561A GB951667A (en) | 1961-04-25 | 1961-04-25 | New water soluble azo dyestuffs containing quaternary ammonium groups |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1469561A GB951667A (en) | 1961-04-25 | 1961-04-25 | New water soluble azo dyestuffs containing quaternary ammonium groups |
Publications (1)
Publication Number | Publication Date |
---|---|
GB951667A true GB951667A (en) | 1964-03-11 |
Family
ID=10045918
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1469561A Expired GB951667A (en) | 1961-04-25 | 1961-04-25 | New water soluble azo dyestuffs containing quaternary ammonium groups |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB951667A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0022209A2 (en) * | 1979-07-07 | 1981-01-14 | Bayer Ag | Fluor-triazine dyestuffs and their use in dyeing cellulosic fibrous materials |
EP0059355A2 (en) * | 1981-02-26 | 1982-09-08 | Bayer Ag | Use of reactive dyestuffs in dyeing and printing of hydroxylgroups containing fibrous materials |
EP0062824A2 (en) * | 1981-04-08 | 1982-10-20 | Bayer Ag | Cationic azo dyestuffs containing sulfonic-acid groups, their preparation and their use |
EP0062825A2 (en) * | 1981-04-08 | 1982-10-20 | Bayer Ag | Water-soluble triazine compounds, their preparation and their use |
US7375222B2 (en) | 2002-02-05 | 2008-05-20 | Astellas Pharma Inc. | 2,4,6-Triamino-1,3,5-triazine derivative |
-
1961
- 1961-04-25 GB GB1469561A patent/GB951667A/en not_active Expired
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4503224A (en) * | 1979-07-07 | 1985-03-05 | Bayer Aktiengesellschaft | Halogenotriazinyl dyestuffs |
JPS5614562A (en) * | 1979-07-07 | 1981-02-12 | Bayer Ag | Basic halogenotriazinyl dyes* their manufacture and their use for dyeing celluloseecontaining fibrous matter |
EP0022209A3 (en) * | 1979-07-07 | 1982-03-17 | Bayer Ag | Basic halogen-triazine dyestuffs and their preparation, and their use in dyeing cellulosic fibrous materials |
EP0022209A2 (en) * | 1979-07-07 | 1981-01-14 | Bayer Ag | Fluor-triazine dyestuffs and their use in dyeing cellulosic fibrous materials |
JPH0335340B2 (en) * | 1979-07-07 | 1991-05-27 | Bayer Ag | |
EP0059355A2 (en) * | 1981-02-26 | 1982-09-08 | Bayer Ag | Use of reactive dyestuffs in dyeing and printing of hydroxylgroups containing fibrous materials |
EP0059355A3 (en) * | 1981-02-26 | 1983-04-06 | Bayer Ag | Use of reactive dyestuffs in dyeing and printing of hydroxylgroups containing fibrous materials |
EP0062824A3 (en) * | 1981-04-08 | 1983-04-13 | Bayer Ag | Cationic azo dyestuffs containing sulfonic-acid groups, their preparation and their use |
EP0062825A3 (en) * | 1981-04-08 | 1983-06-01 | Bayer Ag | Water-soluble triazine compounds, their preparation and their use |
EP0062825A2 (en) * | 1981-04-08 | 1982-10-20 | Bayer Ag | Water-soluble triazine compounds, their preparation and their use |
US4839468A (en) * | 1981-04-08 | 1989-06-13 | Bayer Aktiengesellschaft | N-(hydroxy-sulpho-naphthyamino-triazinyl)-arylene-diamines |
EP0062824A2 (en) * | 1981-04-08 | 1982-10-20 | Bayer Ag | Cationic azo dyestuffs containing sulfonic-acid groups, their preparation and their use |
US7375222B2 (en) | 2002-02-05 | 2008-05-20 | Astellas Pharma Inc. | 2,4,6-Triamino-1,3,5-triazine derivative |
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