GB856348A - Improvements in or relating to water-insoluble monoazo dyestuffs containing carboxylic ester groups - Google Patents
Improvements in or relating to water-insoluble monoazo dyestuffs containing carboxylic ester groupsInfo
- Publication number
- GB856348A GB856348A GB23501/57A GB2350157A GB856348A GB 856348 A GB856348 A GB 856348A GB 23501/57 A GB23501/57 A GB 23501/57A GB 2350157 A GB2350157 A GB 2350157A GB 856348 A GB856348 A GB 856348A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- dyestuffs
- nitro
- formula
- ch2ome
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Compounds of formula: <FORM:0856348/IV(b)/1> Where R2 is Me, Et, CH2Cl, CH2OMe, CF3 or C Cl3, R3 is Me, Et, CH2 Cl or CH2OMe, R4 is an alkyl radicle of 1-4 C atoms or CH2 Cm H2m OCO R3, R5 is H or NH-y-R2, X is H or, when R5 is H, may also be Cl, Br, Me Et, OMe or OEt, y is a carbonyl, carbonyloxy, sulphur, sulphoxide or sulphonyl bridge, m is 1, 2 or 3 and n is 1 or 2 are used as coupling components for azo dyes (see Group IV(c)) and stated to be new. They are made by reacting compounds of formula: <FORM:0856348/IV(b)/2> Where Z is H, Me, Et, propyl, isopropyl or hydroxy-methyl, -ethyl or -propyl, or of formula: <FORM:0856348/IV(b)/3> With a functional derivative of an appropriate aliphatic carboxylic acid, in the latter instance y-R2 in the products is COR3. Many components are specified in list and tabular form and in Example 13 l-di-(hydroxyethyl)-amino-3-aminobenzene is triacetylated with acetic anhydride. Reference has been directed by the Comptroller to Specifications 744,577, 764,308, 764,309 and 774,611.ALSO:The invention comprises dyestuffs of formula: <FORM:0856348/IV (c)/1> where R1 is a residue of a benzene, naphthalene or heterocyclic diazo component free form sulphonic or a carboxylic acid groups, R2 is Me, Et, CH2Cl, CH2OMe, CF3 or CCl3, R3 is Me Et, CH2Cl or CH2OMe, R4 is an alkyl radical of 1-4 C atoms or -CH2-CmH2m-O-CO-R3, R5 is H or -NH-Y-R2, X is H or, when R5 is H, is also Cl, Br Me, Et, OMe or OEt, OMe and OEt being excluded when R1 is: <FORM:0856348/IV (c)/2> where Z is Hlg or NO2, Y is carbonyl, carbonyloxy, sulphur, sulphoxide or sulphonyl bridge, n is 1 or 2 and m is 1, 2 or 3. Of especial interest are dyestuffs of formula: <FORM:0856348/IV (c)/3> where R4, n and m are as above, S is NO2 or MeSO2-t is H, Cl, Br, MeO, CF3, CN or MeSO2 and R2 and R3 are Me or Et. The dyestuffs are made by coupling, preferably in acid solution, an appropriate diazotised amine R, NH2 with the necessary coupling component. Dyestuffs in which R4 is CH2-Z where Z is H, Me, Et, propyl or isopropyl or CH2-CmH2m-1 H2-n-(O-COR3)n and derived from benzene or naphthalene diazo compounds, may also be made by acylating corresponding dyestuffs where -(O-COR3)n is replaced by (OH)n. Indicated amines corresponding to R1 are 4-nitroaniline, 1-amino-4-alkylsulphonylbenzene and its 2-mono- or 2, 6-di-substituted derivatives, 1-amino-4-alkylsulphonylnaphthalene and 1- naphthylamine -4- sulphonic acid fluoride and their derivatives and 2- aminothiazole, -thiophene and thio-diazole and their derivatives. The dyestuffs dye cellulose ester, polyamide, polyvinyl, terephthalic acid ester and polyacrylonitrile fibres in orange, red or violet shades. A large number of illustrative examples are provided the values for R1, R2, R3, R4 R5, x, y, n, m, s, t and z in the reactants used being selected from those specified above, additional diazo components being 2- amino -6- methylsulphonyl-or -nitrobenzothiazole, 2- amino-1, 3, 5-, -5- nitro- 1, 3, 4- and 4- phenylthiodiazoles, 2- amino -5- thiocyanonitro- and -cyanothiazoles, 2-amino -5- nitro -4- methylthiazole, 2- aminothiazole -5- carboxylic acid esters, 2-amino -3- nitro -5- acetylthiophene, 1- amino-2, 4- dicyano- and -nitro-, 2- chloro -4- cyano-, 2- cyano -4- nitro -6- chloro -2, 4- dinitro -6-chloro- and -cyanobenzenes, 1- amino -2, 4-dinitrobenzene -6- sulphonethylamide, 1-amino -4- nitrobenzene -2- sulphonfluoride, 4-methylsulphonyl- and -fluorosulphonylnaphthalene. Reference has been directed by the Comptroller to Specifications 744,877, 764,308, 764,309 and 774,611.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH856348X | 1956-07-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB856348A true GB856348A (en) | 1960-12-14 |
Family
ID=4542713
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB23501/57A Expired GB856348A (en) | 1956-07-25 | 1957-07-24 | Improvements in or relating to water-insoluble monoazo dyestuffs containing carboxylic ester groups |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB856348A (en) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3268507A (en) * | 1962-08-10 | 1966-08-23 | Bayer Ag | Water-insoluble monoazo dyestuffs |
US3342803A (en) * | 1963-02-21 | 1967-09-19 | Ciba Ltd | Water-insoluble monoazo-dyestuffs |
US3398135A (en) * | 1963-02-15 | 1968-08-20 | Sandoz Ltd | 2-cyano-4-nitro-6-halogeno-2'-acylamino-4'-dialkylamino-1, 1'-azobenzene dyes |
US3406165A (en) * | 1962-07-11 | 1968-10-15 | Bayer Ag | Monoazo dyestuffs |
US3406164A (en) * | 1965-01-14 | 1968-10-15 | Sandoz Ltd | Disperse dyes of the monoazo series |
DE2201113A1 (en) * | 1971-01-11 | 1972-08-03 | Ici Ltd | Disperse azo dyes |
WO1995020014A1 (en) * | 1994-01-19 | 1995-07-27 | Zeneca Limited | Monoazo dyes containing a fluorosulphonyl group and use thereof |
US5973127A (en) * | 1996-06-25 | 1999-10-26 | Basf Aktiengesellschaft | Monoazo dyes substituted by haloalkylcarbamate and sulphonylfluoride groups |
-
1957
- 1957-07-24 GB GB23501/57A patent/GB856348A/en not_active Expired
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3406165A (en) * | 1962-07-11 | 1968-10-15 | Bayer Ag | Monoazo dyestuffs |
US3268507A (en) * | 1962-08-10 | 1966-08-23 | Bayer Ag | Water-insoluble monoazo dyestuffs |
US3398135A (en) * | 1963-02-15 | 1968-08-20 | Sandoz Ltd | 2-cyano-4-nitro-6-halogeno-2'-acylamino-4'-dialkylamino-1, 1'-azobenzene dyes |
US3342803A (en) * | 1963-02-21 | 1967-09-19 | Ciba Ltd | Water-insoluble monoazo-dyestuffs |
US3406164A (en) * | 1965-01-14 | 1968-10-15 | Sandoz Ltd | Disperse dyes of the monoazo series |
DE2201113A1 (en) * | 1971-01-11 | 1972-08-03 | Ici Ltd | Disperse azo dyes |
WO1995020014A1 (en) * | 1994-01-19 | 1995-07-27 | Zeneca Limited | Monoazo dyes containing a fluorosulphonyl group and use thereof |
US5739299A (en) * | 1994-01-19 | 1998-04-14 | Zeneca Limited | Monoazo dyes which are free from water-solubilizing groups and which contain a fluorosulphonyl group and process for colouring polyamides and polyester materials therewith |
US5973127A (en) * | 1996-06-25 | 1999-10-26 | Basf Aktiengesellschaft | Monoazo dyes substituted by haloalkylcarbamate and sulphonylfluoride groups |
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