GB599834A - Improvements in or relating to the manufacture of azodyestuffs - Google Patents
Improvements in or relating to the manufacture of azodyestuffsInfo
- Publication number
- GB599834A GB599834A GB17989/45A GB1798945A GB599834A GB 599834 A GB599834 A GB 599834A GB 17989/45 A GB17989/45 A GB 17989/45A GB 1798945 A GB1798945 A GB 1798945A GB 599834 A GB599834 A GB 599834A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- indazol
- chloro
- nitro
- coupling
- 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
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
- C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Azo dyestuffs are formed in substance or on the fibre by coupling an arylide of an orthooxycarboxylic or acylacetic acid with a diazo derivative of 7-amino-indazol in which the benzene nucleus may carry substituents, such as halogen, alkyl, alkoxy, aryloxy, acylamino, nitro, sulphone, sulphamido or arylazo groups, which do not confer solubility in water. The coupling may be effected in the presence of a metallizing agent, or the dyed fibre may be treated with a copper salt in presence of an organic base containing at least one oxyalkyl group, e.g. mono-, di- and tri-ethanolamines, propanolamine and diethyl-oxyethylamine. The following examples are given: (1) cotton is foularded in a bath containing the b -naphthylamide of 2,3-oxynaphthoic acid and developed in a diazotized solution containing 7-amino-indazol to which is added neutral copper acetate and magnesium sulphate; (2) the 7-amino-indazol of (1) is replaced by 4-chloro-7-aminoindazol, obtainable by diazotizing 3-nitro - 6 - chloro - 2 - acetylaminotoluene, boiling, and reducing the 4-chloro-7-nitro-indazol so obtained; (3) a mixture of 7-amino-indazol and 4-chloro-7-amino-indazol is diazotized and coupled with b -naphthylamide of 2,3-oxynaphthoic acid on cotton, and the dyeing after-treated with a solution containing copper sulphate and monoethanolamine; (4) the previous example is repeated using 4-nitro-7-amino-indazol, obtained by nitrating 7-amino-indazol in glacial acetic acid and then saponifying; (5) example (3) is repeated using 4-diethylsulphamido-7-amino-indazol obtained by (a) treating 1 - acetylamino - 2 - methyl - 3 - chloro - 6 - nitrobenzene with sodium sulphide and sulphur, (b) chlorinating the 2,21-dimethyldiphenyl sulphide so formed to yield 2-methyl-3 - acetylamino - 4 - nitrobenzene sulphochloride, (c) treating with diethylamine to give 2 - methyl - 3 - acetylamino - 4 - nitrobenzene - diethylsulphamide, (d) saponifying, (e) diazotizing to give 7-nitro-4-diethylsulphamidoindazol and then (f) reducing with iron powder and acetic acid; (6) example (3) is repeated using 4-methoxy-7-amino-indazole as base and the anilide of 2,3-oxynaphthoic acid as coupling agent, the former being prepared by (a) heating 3 - nitro - 6 - chloro - 2 - aminotoluene with methyl alcohol and potash to give 3-nitro-6-methoxy-2-aminotoluene which is then (b) diazotized and poured into hot sodium acetate solution to give 4-methoxy-7-nitroindazol which is finally (c) reduced with iron powder and acetic acid; (7) example (3) is repeated using 5 - chloro - 7 - amino - indazol prepared by diazotizing 3-nitro - 5 - chloro - 2 - aminotoluene, pouring into a hot solution of sodium acetate, and reducing with iron powder and hydrochloric acid; (8) example (3) is repeated using 4 - benzoylamino - 5 - methyl - 7 - amino - indazol, which is prepared by reducing 4-nitro-5-methyl-indazol with iron powder and acetic acid, benzoylating the amino group, nitrating in the presence of acetic acid, and again reducing. A Table is also included showing the various colours obtained with a number of specified bases and coupling agents before and after coppering. Specification 518,987 is referred to. The Specification as open to inspection under Sect. 91 refers generally to the production of dyestuffs, in substance or on the fibre, from a coupling agent having a substantive character and an amino-indazol of the formula <FORM:0599834/IV/1> in which X is a hydrogen or halogen atom, Y is hydrogen or an alkyl, aralkyl or cycloalkyl group, and in which the benzene nucleus may carry substituents which do not confer solubility in water. The dyestuffs may then be converted into their metalliferous complexes. Examples given include the diazotizing of 6-amino-indazol and coupling with b -naphthylamide of b -oxynaphthoic acid in the presence of neutral copper acetate; diazotizing 3-chloro-6-amino-indazol and coupling with b -naphthylamide of b -oxynaphthoic acid in the presence of copper acetate; diazotizing 6-amino-indazol, coupling with b -naphthylamide of b -oxynaphthoic acid and coppering with copper sulphate in presence of monoethanolamine; diazotizing 3 - chloro - 6 - amino - indazol, coupling with b -naphthylamide of b -oxynaphthoic acid and coppering with copper sulphate in presence of triethanolamine; in other similar examples the following amino-indazoles are used, 5-chloro-6-amino-indazol, a mixture of 1- and 2 - methyl - 6 - amino - indazol, 4-amino - 7 - benzoylamino - indazol, o - chloroaniline --> 6 - amino - indazol, o - chloro - aniline --> 1- or 2-methyl-6-amino-indazol, 5- - amino - indazol, 6 - chloro - 5 - amino - indazol, o-nitraniline --> 6-amino-indazol. A Table is given of many diazotizable bases and coupling components showing the colours obtained before and after coppering. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR599834X | 1943-04-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB599834A true GB599834A (en) | 1948-03-22 |
Family
ID=8969816
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB17989/45A Expired GB599834A (en) | 1943-04-08 | 1945-07-13 | Improvements in or relating to the manufacture of azodyestuffs |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB599834A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2795575A (en) * | 1954-04-30 | 1957-06-11 | Cfmc | Azo dyes |
US4036976A (en) * | 1973-04-05 | 1977-07-19 | Sandoz, Inc. | Substituted imidazolinylamino-indazoles |
EP2178870A1 (en) * | 2007-08-17 | 2010-04-28 | LG Life Sciences Ltd. | Indole and indazole compounds as an inhibitor of cellular necrosis |
JP2017508766A (en) * | 2014-03-26 | 2017-03-30 | メルク・シャープ・アンド・ドーム・コーポレーションMerck Sharp & Dohme Corp. | TrkA kinase inhibitors, compositions and methods thereof |
-
1945
- 1945-07-13 GB GB17989/45A patent/GB599834A/en not_active Expired
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2795575A (en) * | 1954-04-30 | 1957-06-11 | Cfmc | Azo dyes |
US4036976A (en) * | 1973-04-05 | 1977-07-19 | Sandoz, Inc. | Substituted imidazolinylamino-indazoles |
EP2178870A1 (en) * | 2007-08-17 | 2010-04-28 | LG Life Sciences Ltd. | Indole and indazole compounds as an inhibitor of cellular necrosis |
JP2010536846A (en) * | 2007-08-17 | 2010-12-02 | エルジー・ライフ・サイエンシーズ・リミテッド | Indole and indazole compounds as cell necrosis inhibitors |
EP2178870A4 (en) * | 2007-08-17 | 2012-04-11 | Lg Life Sciences Ltd | Indole and indazole compounds as an inhibitor of cellular necrosis |
JP2017508766A (en) * | 2014-03-26 | 2017-03-30 | メルク・シャープ・アンド・ドーム・コーポレーションMerck Sharp & Dohme Corp. | TrkA kinase inhibitors, compositions and methods thereof |
JP2017512786A (en) * | 2014-03-26 | 2017-05-25 | メルク・シャープ・アンド・ドーム・コーポレーションMerck Sharp & Dohme Corp. | TrkA kinase inhibitors, compositions and methods thereof |
US9862707B2 (en) * | 2014-03-26 | 2018-01-09 | Merck Sharp & Dohme Corp. | TrkA kinase inhibitors, compositions and methods thereof |
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