GB831840A - Monoazo dyestuffs containing sulphonic acid-(sulphonyl)í¡í¡ps - Google Patents
Monoazo dyestuffs containing sulphonic acid-(sulphonyl)í¡í¡psInfo
- Publication number
- GB831840A GB831840A GB37192/57A GB3719257A GB831840A GB 831840 A GB831840 A GB 831840A GB 37192/57 A GB37192/57 A GB 37192/57A GB 3719257 A GB3719257 A GB 3719257A GB 831840 A GB831840 A GB 831840A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- amino
- sulphonic acid
- sulpho
- chloro
- 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
- 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 title 1
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000002843 carboxylic acid group Chemical group 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 2
- 210000002268 wool Anatomy 0.000 abstract 2
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 abstract 1
- BOTOIHAKCFLTEG-UHFFFAOYSA-N 2-amino-n-methylsulfonylbenzenesulfonamide Chemical class CS(=O)(=O)NS(=O)(=O)C1=CC=CC=C1N BOTOIHAKCFLTEG-UHFFFAOYSA-N 0.000 abstract 1
- XJQRCFRVWZHIPN-UHFFFAOYSA-N 3-amino-4-chlorobenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1Cl XJQRCFRVWZHIPN-UHFFFAOYSA-N 0.000 abstract 1
- JZEMWPDXKQPACX-UHFFFAOYSA-N 3-amino-N-(benzenesulfonyl)-4-chlorobenzenesulfonamide Chemical compound C1(=CC=CC=C1)S(=O)(=O)NS(=O)(=O)C=1C=C(C(=CC1)Cl)N JZEMWPDXKQPACX-UHFFFAOYSA-N 0.000 abstract 1
- QRRXGUYBWCPMGI-UHFFFAOYSA-N 3-amino-n-(benzenesulfonyl)benzenesulfonamide Chemical compound NC1=CC=CC(S(=O)(=O)NS(=O)(=O)C=2C=CC=CC=2)=C1 QRRXGUYBWCPMGI-UHFFFAOYSA-N 0.000 abstract 1
- TXWROWPXUQZXFZ-UHFFFAOYSA-N 4-amino-n-(benzenesulfonyl)benzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NS(=O)(=O)C1=CC=CC=C1 TXWROWPXUQZXFZ-UHFFFAOYSA-N 0.000 abstract 1
- FSTWYHAPODNOCA-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)NS(=O)(=O)C1=C(C=C(C=C1)Cl)N Chemical class C1(=CC=CC=C1)S(=O)(=O)NS(=O)(=O)C1=C(C=C(C=C1)Cl)N FSTWYHAPODNOCA-UHFFFAOYSA-N 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 abstract 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 229920002635 polyurethane Polymers 0.000 abstract 1
- 239000004814 polyurethane Substances 0.000 abstract 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 abstract 1
- 150000003217 pyrazoles Chemical class 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
- C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
- C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention comprises dyestuffs of formula R1SO2NHSO2R.N=NR3 where R is a benzene residue which may contain substituents other than sulphonic or carboxylic acid groups, R1 is an alkyl or phenyl radicle which may contain substituents except sulphonic or carboxylic acid groups and R3 is the residue of a 1-sulphoaryl-3-methyl-5-pyrazolone or aminopyrazole linked to the azo bridge in the 4-position, the sulphoaryl groups of which may be substituted by halogen atoms or alkyl radicles. The dyestuffs are made by coupling, in weakly acid to alkaline media, diazotized amines of formula R1SO2NHSO2.R.NH2 with appropriate pyrazolones or pyrazoles. Specified diazo components are 1-amino- and 1 - amino - 5 - chloro - benzene - 2 - sulphonic acid (phenylsulphonyl) - amides, 1 - amino - benzene - 2 - sulphonic acid -(41 - chloro-, -methyl- and -acetylamino-, 21 - methyl- and -21,51- and -31,41 - dichloro - phenylsulphonyl)-amides, 1 - amino - benzene - 3 - sulphonic acid -(phenylsulphonyl)-amide and its 21- and 41-methyl and 41-chloro- and -acetylamino derivatives, 1-amino-6-chlorobenzene-3-sulphonic acid -(phenyl-sulphonyl)-amide and its 41-methyl and 31,41-dichloro derivatives, 1-aminobenzene-4 - sulphonic acid -(phenyl - sulphonyl) - amide and its 21- and 41-methyl derivatives. Specified coupling components are 1-(21-, 31- and 41-sulpho-, 21-methyl- and -chloro- and 21,51-dichloro - 41 - sulpho- and 21 - chloro- and 21,31,61 - trichloro - 51 - sulpho - phenyl) - 3 - methyl - 5 - pyrazolones, 1 - (21 - naphthyl - 61 - sulpho and -61,81 - disulpho) - 3 - methyl - 5 - pyrazolones and 1-(31-sulphophenyl) and -(21-naphthyl - 81 - sulpho) - 3 - methyl - 5 - amino-pyrazoles. The dyestuffs dye wool and polyamide and polyurethane fibres from a weakly acid bath in yellow shades. Examples are provided illustrating the preparation of the dyestuffs and their uses in dyeing wool, the components used being selected from those indicated above with the addition of 1-amino-benzene-2-sulphonic acid -(21,51-dimethyl-41-chlorophenyl)-, 1 - amino - 2 - chlorobenzene - 5-sulphonic acid -(21,51-dichlorophenyl) and 1-aminobenzene - 2 - sulphonic acid -(methyl)-sulphonylamides and 1-(21-naphthyl-41,81-disulpho) - 3 - methyl - 5 - pyrazolones and 1 - (21,51-disulphophenyl) - 3 - methyl - 5 - aminopyrazole.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE831840X | 1956-12-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB831840A true GB831840A (en) | 1960-04-06 |
Family
ID=6754581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB37192/57A Expired GB831840A (en) | 1956-12-05 | 1957-11-28 | Monoazo dyestuffs containing sulphonic acid-(sulphonyl)í¡í¡ps |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB831840A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4159265A (en) * | 1973-07-14 | 1979-06-26 | Bayer Aktiengesellschaft | Phenylazopyrazolo dyestuffs including disulfimide substituent |
-
1957
- 1957-11-28 GB GB37192/57A patent/GB831840A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4159265A (en) * | 1973-07-14 | 1979-06-26 | Bayer Aktiengesellschaft | Phenylazopyrazolo dyestuffs including disulfimide substituent |
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