GB954100A - Coppered azo dyestuffs containing triazole residues - Google Patents
Coppered azo dyestuffs containing triazole residuesInfo
- Publication number
- GB954100A GB954100A GB4240461A GB4240461A GB954100A GB 954100 A GB954100 A GB 954100A GB 4240461 A GB4240461 A GB 4240461A GB 4240461 A GB4240461 A GB 4240461A GB 954100 A GB954100 A GB 954100A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- coppering
- coupling
- diazotising
- amino
- 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
- 125000001425 triazolyl group Chemical group 0.000 title 1
- 239000000975 dye Substances 0.000 abstract 6
- 230000008878 coupling Effects 0.000 abstract 5
- 238000010168 coupling process Methods 0.000 abstract 5
- 238000005859 coupling reaction Methods 0.000 abstract 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 4
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 abstract 3
- 150000008049 diazo compounds Chemical class 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- -1 aminoazo Chemical group 0.000 abstract 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 abstract 1
- QYFYIOWLBSPSDM-UHFFFAOYSA-N 6-aminonaphthalen-1-ol Chemical compound OC1=CC=CC2=CC(N)=CC=C21 QYFYIOWLBSPSDM-UHFFFAOYSA-N 0.000 abstract 1
- 229920003043 Cellulose fiber Polymers 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 239000000987 azo dye Substances 0.000 abstract 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000004696 coordination complex Chemical class 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 abstract 1
- 230000020335 dealkylation Effects 0.000 abstract 1
- 238000006900 dealkylation reaction Methods 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/06—Preparation of azo dyes from other azo compounds by oxidation
-
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention comprises copper-containing azo dyes of formula <FORM:0954100/C3/1> wherein A is the residue of a diazo compound, which may contain a further azo group, in which X is in o-position to the azo group, X is an -O- or -COO- group, B is a p-phenylene or -naphthylene residue, D is an o-naphthylene residue, Y is a hydrogen or halogen atom, m is 0 or 1 and n is 1 or 2. The dyes may be prepared by the usual procedure, for example coupling the diazo compound of a suitable amine (A-NH2) which contains an -OH or COOH group or a group or atom convertible thereto under coppering conditions in o-position to the -NH2 group, with a 2-amino-5-naphthol-7-sulphonic acid, coppering the aminoazo dye obtained, diazotising the metal complex, coupling in p-position with an amino-benzene or -naphthalene, again diazotising and coupling in o-position to an NH2 group in a naphthalene azo component and finally triazolising the o-aminoazo compound. Alternatively by diazotising a 2 - amino - 5 - naphthol - 7 - sulphoric acid in which the hydroxy group is protected by acylation (e.g. with benzenesulphonic acid), coupling in p-position with an amino-benzene or -naphthalene, diazotising the aminoazo dye obtained, coupling with a naphthylamine and triazolising the o-aminoazo compound obtained. The resultant monoazo dye is saponified to remove the acyl group, coupled with a suitable diazo compound and coppered. The coppering reaction is carried out using aqueous copper sulphate and possibly ammonia and includes oxidatiol coppering and coppering with dealkylation. The dyes give brown and green shades on cellulose fibres. Examples describe the preparation of the dyes.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF32635A DE1285644B (en) | 1960-11-26 | 1960-11-26 | Process for the production of metal-containing azo dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB954100A true GB954100A (en) | 1964-04-02 |
Family
ID=7094716
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4240461A Expired GB954100A (en) | 1960-11-26 | 1961-11-27 | Coppered azo dyestuffs containing triazole residues |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH438537A (en) |
| DE (1) | DE1285644B (en) |
| GB (1) | GB954100A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009057676A1 (en) * | 2007-11-02 | 2009-05-07 | Nippon Kayaku Kabushiki Kaisha | Azo compound, and dye-containing polarizing film comprising the same |
| US8643809B2 (en) | 2006-06-01 | 2014-02-04 | Nippon Kayaku Kabushiki Kaisha | Azo compound and salt thereof, and dye-containing polarizing film comprising the compound or salt |
| US9354371B2 (en) | 2008-05-20 | 2016-05-31 | Nippon Kayaku Kabushiki Kaisha | Azo compounds, and dye-based polarizing films and polarizing plates comprising the same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE737941C (en) * | 1938-11-15 | 1943-08-02 | Ig Farbenindustrie Ag | Process for the preparation of copper-containing disazo dyes |
-
1960
- 1960-11-26 DE DEF32635A patent/DE1285644B/en active Pending
-
1961
- 1961-10-30 CH CH1250861A patent/CH438537A/en unknown
- 1961-11-27 GB GB4240461A patent/GB954100A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8643809B2 (en) | 2006-06-01 | 2014-02-04 | Nippon Kayaku Kabushiki Kaisha | Azo compound and salt thereof, and dye-containing polarizing film comprising the compound or salt |
| US9213130B2 (en) | 2006-06-01 | 2015-12-15 | Nippon Kayaku Kabushiki Kaisha | Azo compound and salt thereof, and dye-containing polarizing film comprising the compound or salt |
| WO2009057676A1 (en) * | 2007-11-02 | 2009-05-07 | Nippon Kayaku Kabushiki Kaisha | Azo compound, and dye-containing polarizing film comprising the same |
| US8232375B2 (en) | 2007-11-02 | 2012-07-31 | Nippon Kayaku Kabushiki Kaisha | Azo compound, and dye-containing polarizing film comprising the same |
| US9354371B2 (en) | 2008-05-20 | 2016-05-31 | Nippon Kayaku Kabushiki Kaisha | Azo compounds, and dye-based polarizing films and polarizing plates comprising the same |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1285644B (en) | 1968-12-19 |
| CH438537A (en) | 1967-06-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB954100A (en) | Coppered azo dyestuffs containing triazole residues | |
| GB299331A (en) | Manufacture of azo-dyestuffs and intermediate products | |
| GB987740A (en) | Water-insoluble disazo dyestuffs and process for their manufacture | |
| GB907383A (en) | Disazo and trisazo dyestuffs and copper complexes thereof | |
| GB944909A (en) | Improvements relating to heavy metal-containing formazane dyestuffs and their use | |
| GB458843A (en) | The manufacture of azodyestuffs capable of forming metallic complex compounds | |
| US1849573A (en) | Disazo-dyestuffs and process of making same | |
| GB1130348A (en) | Metal-containing disazo dyestuffs and process for their manufacture | |
| GB1015789A (en) | Metalliferous azo-dyestuffs and process for preparing them | |
| GB864276A (en) | Metallized azo dyestuffs containing triazole rings | |
| GB853013A (en) | Monoazo dyestuffs containing triazole rings | |
| GB760347A (en) | Azo-dyestuffs, metalliferous azo-dyestuffs and process for making them | |
| GB786918A (en) | Improvements relating to disazo dyestuffs, complex copper compounds thereof, and their use | |
| GB866386A (en) | Metallized disazo dyestuffs containing triazole rings | |
| GB589536A (en) | Manufacture of tetrakisazo-dyestuffs capable of being metallised | |
| GB490389A (en) | The manufacture of azodyestuffs | |
| GB901927A (en) | Copper-containing polyazo dyestuffs | |
| GB1001066A (en) | New metallisable monoazo dyes containing halopyrimidine residues and their copper and nickel complexes | |
| GB803810A (en) | Copper-containing trisazo dyestuffs | |
| GB819841A (en) | Copper-containing disazo dyestuffs | |
| GB901900A (en) | Metal complex compounds of triazole azo dyestuffs | |
| GB700211A (en) | Manufacture of azo dyestuffs | |
| GB874545A (en) | New mono-azo-dyestuffs containing halo-triazinylamino residues and their manufactureand use | |
| GB744406A (en) | Manufacture of azo-dyestuffs | |
| GB948837A (en) | New azo dyestuffs containing disulphonimide groups and their metal complexes |