GB948837A - New azo dyestuffs containing disulphonimide groups and their metal complexes - Google Patents
New azo dyestuffs containing disulphonimide groups and their metal complexesInfo
- Publication number
- GB948837A GB948837A GB4275361A GB4275361A GB948837A GB 948837 A GB948837 A GB 948837A GB 4275361 A GB4275361 A GB 4275361A GB 4275361 A GB4275361 A GB 4275361A GB 948837 A GB948837 A GB 948837A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulpho
- methanesulpho
- isopropylimide
- pyrazolone
- reacting
- 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
- 239000002184 metal Substances 0.000 title 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 abstract 10
- 239000000975 dye Substances 0.000 abstract 5
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 abstract 4
- LLCOIQRNSJBFSN-UHFFFAOYSA-N methane;sulfurochloridic acid Chemical compound C.OS(Cl)(=O)=O LLCOIQRNSJBFSN-UHFFFAOYSA-N 0.000 abstract 3
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 abstract 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 abstract 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 abstract 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 2
- 230000008878 coupling Effects 0.000 abstract 2
- 238000010168 coupling process Methods 0.000 abstract 2
- 238000005859 coupling reaction Methods 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 abstract 2
- SWFNPENEBHAHEB-UHFFFAOYSA-N 2-amino-4-chlorophenol Chemical compound NC1=CC(Cl)=CC=C1O SWFNPENEBHAHEB-UHFFFAOYSA-N 0.000 abstract 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- QSACCXVHEVWNMX-UHFFFAOYSA-N N-acetylanthranilic acid Chemical compound CC(=O)NC1=CC=CC=C1C(O)=O QSACCXVHEVWNMX-UHFFFAOYSA-N 0.000 abstract 1
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 abstract 1
- ZMJZYXKPJWGDGR-UHFFFAOYSA-N aminosulfamic acid Chemical compound NNS(O)(=O)=O ZMJZYXKPJWGDGR-UHFFFAOYSA-N 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000002843 carboxylic acid group Chemical group 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001844 chromium Chemical class 0.000 abstract 1
- 229910052804 chromium Inorganic materials 0.000 abstract 1
- 239000011651 chromium Substances 0.000 abstract 1
- 150000001868 cobalt Chemical class 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- 230000009918 complex formation Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 1
- 150000001989 diazonium salts Chemical class 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 239000004922 lacquer Substances 0.000 abstract 1
- 150000002790 naphthalenes Chemical class 0.000 abstract 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 abstract 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 abstract 1
- 235000010265 sodium sulphite Nutrition 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/04—Azo compounds in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
2 - Aminophenol - 4 - sulpho - (methanesulpho) -methylimide is prepared by reacting 2 - nitrophenol -4-sulphomethylamide with methane sulphochloride to give 2 - nitrophenol - 4 - sulpho -(methanesulpho) - methylimide and reducing this by catalytic hydrogenation; 2 - Aminophenol - 4 -sulpho - (methanesulpho) - isobutyl - and isopropyl -imides are also specified. 1 - Phenyl - 3 - methyl-5-pyrazolone - 31 -sulpho-(methanesulpho) -isopropylimide is prepared by reacting 3 - nitrobenzenesulpho - isopropylamide with methane sulphochloride and hydrogenating the product to give 3 - aminobenzene - sulpho -(methanesulpho) - isopropylimide, diazotizing this compound reacting the diazonium compound with sodium sulphite and saponifying the hydrazine -N - sulphonic acid obtained to give 3 -hydrazino - benzene - sulpho - (methanesulpho) -isopropylimide and reacting this with acetoacetamide. 1 - Amino - 2 - carboxybenzene - 5 - sulpho -(methanesulpho) - isopropylimide is prepared by reacting N - acetyl - anthranilic acid - 5 - sulpho-isopropylimide with methane sulphochloride and saponifying the product.ALSO:The invention comprises metallizable dyes of formula <FORM:0948837/C3/1> wherein A is the radical of a diazo component of the benzene series, X is a metallizable group or a substituent convertible into a metallizable group under metallizing conditions in ortho-position to the azo group, B is an azo component of the pyrazolone or naphthalene series coupling ortho to -OH and R and R1 are alkyl radicals containing up to 5 carbon atoms, which may be substituted; and chromium, copper and cobalt complexes thereof. The dyes are prepared by the usual coupling procedure using suitable components one of which contains a disulphonimide group and metallized by known methods using cobalt-, chromium- or copper-yielding agents. A preferred class of the dyes are those which are free of sulphonic acid and carboxylic acid groups not taking part in complex formation which are used to dye lacquers. In examples the following dyes are prepared and converted into their cobalt and chromium complexes: 2 - amino - phenol - 4 - sulpho - (methanesulpho)-methylimide --> 1 - phenyl - 3 - methyl - 5 - pyrazolone; 2 - aminophenol - 4 - sulpho - (methanesulpho) - isobutylimide--> b - naphthol; 2 - aminophenol - 4 - sulpho - (methanesulpho) - isopropylimide --> b - naphthol; 2 - amino - 4 - chlorophenol--> 1 - phenyl - 3 - methyl - 5 - pyrazolone - 31 - sulpho - (methanesulpho) - isopropylimide; 1 - amino - 2 - carboxy - benzene - 5 - sulpho - (methanesulpho)-isopropylimide--> 1 phenyl - 3 - methyl - 5 - pyrazolone.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF32658A DE1219147B (en) | 1960-11-30 | 1960-11-30 | Process for the preparation of metal complex compounds of azo dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB948837A true GB948837A (en) | 1964-02-05 |
Family
ID=7094726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4275361A Expired GB948837A (en) | 1960-11-30 | 1961-11-29 | New azo dyestuffs containing disulphonimide groups and their metal complexes |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE610868A (en) |
| DE (1) | DE1219147B (en) |
| GB (1) | GB948837A (en) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH247715A (en) * | 1946-01-31 | 1947-03-31 | Ag J R Geigy | Process for the preparation of a sulfonic acid group-free monoazo dye of the pyrazolone series. |
| DE1039676B (en) | 1956-12-05 | 1958-09-25 | Bayer Ag | Process for the preparation of monoazo dyes |
| FR1208272A (en) * | 1957-05-31 | 1960-02-23 | Basf Ag | Process for the production of azo dyes |
-
1960
- 1960-11-30 DE DEF32658A patent/DE1219147B/en active Pending
-
1961
- 1961-11-28 BE BE610868A patent/BE610868A/en unknown
- 1961-11-29 GB GB4275361A patent/GB948837A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE610868A (en) | 1962-03-16 |
| DE1219147B (en) | 1966-06-16 |
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