GB868474A - Improvements relating to monoazo-pyrazole dyestuffs and their use - Google Patents
Improvements relating to monoazo-pyrazole dyestuffs and their useInfo
- Publication number
- GB868474A GB868474A GB7389/60A GB738960A GB868474A GB 868474 A GB868474 A GB 868474A GB 7389/60 A GB7389/60 A GB 7389/60A GB 738960 A GB738960 A GB 738960A GB 868474 A GB868474 A GB 868474A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amide
- substituents
- dyes
- acid
- residue
- 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
- 239000000975 dye Substances 0.000 abstract 7
- -1 sulphonyl group Chemical group 0.000 abstract 6
- 125000003118 aryl group Chemical group 0.000 abstract 5
- 125000001931 aliphatic group Chemical group 0.000 abstract 3
- 150000001408 amides Chemical class 0.000 abstract 3
- 230000008878 coupling Effects 0.000 abstract 3
- 238000010168 coupling process Methods 0.000 abstract 3
- 238000005859 coupling reaction Methods 0.000 abstract 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004104 aryloxy group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 238000004043 dyeing Methods 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 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
- 210000002268 wool Anatomy 0.000 abstract 2
- FMKMKBLHMONXJM-UHFFFAOYSA-N 5-methyl-2-phenylpyrazol-3-amine Chemical class N1=C(C)C=C(N)N1C1=CC=CC=C1 FMKMKBLHMONXJM-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical group 0.000 abstract 1
- 150000007860 aryl ester derivatives Chemical class 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 150000008048 phenylpyrazoles Chemical class 0.000 abstract 1
- 239000004814 polyurethane Substances 0.000 abstract 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract 1
- 125000000565 sulfonamide group Chemical group 0.000 abstract 1
- 150000003456 sulfonamides Chemical class 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- 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 dyes of formula:- RSO2-A-N=N-B where A is a benzene residue which may be substituted and which has the sulphonyl group m- or pto N2, R is a hydrocarbon, aryloxy or secondary amino radical, the nitrogen substituents of which together have at least 4 C atoms, B is the residue of a 1-aryl-5-aminopyrazole coupling component and the dye has an acid-dissociating group which forms alkali metal salts which are neutral in water. The dyes are made in conventional fashion from appropriate 3- or 4-aminobenzene-1-sulphonyl compounds and aminopyrazoloes. Coupling is preferably effected in an acid medium. R is indicated as an aliphatic, araliphatic, cycloaliphatic or aromatic group with halogens as substituents when aliphatic and, when araliphatic or aromatic, halogens, alkyl, alkoxy, phenoxy, phenylthio, acylamino, triazinylamino, carboxylic acid, carboxylic acid ester and amide, sulphonic acid and aryl ester and amide, acylated sulphonamide with the acyl radical derived from aliphatic or aromatic sulphonic or carboxylic acids and alkyl and aryl sulphony groups as substituents. R, when aryloxy, may be substituted as above, as may the aromatic radicals of the amine residue when R is an amide radical. The N-substituents of R, when an amide, may be joined to form a heterocyclic residue such as piperidine or morpholine. Advantageously the N-substituents have at least 7 C atoms when taken together. The benzene ring of the diazo component and the aryl residue of the pyrazole may be similarly substituted. Phenyl-pyrazoles are preferred coupling components especially 1-phenyl-3-methyl-5-aminopyrazoles. Indicated as acid-dissociating groups are sulphonic acid carboxylic acid, and acylated sulphonamide groups. The dyes dye wool in green and yellow shades and colour silk and synthetic poly-amide and -urethane fibres. Dyes with the sulphonyl substituent in the m-position give greener dyeings than those substituted in the p-position. Examples are provided of the preparation of the dyes and their use in dyeing wool.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH868474X | 1959-03-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB868474A true GB868474A (en) | 1961-05-17 |
Family
ID=4543855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7389/60A Expired GB868474A (en) | 1959-03-03 | 1960-03-02 | Improvements relating to monoazo-pyrazole dyestuffs and their use |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB868474A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2195663A1 (en) * | 1972-08-12 | 1974-03-08 | Bayer Ag | |
| EP0102325A1 (en) * | 1982-08-04 | 1984-03-07 | Ciba-Geigy Ag | Monoazo dyestuffs, their preparation and their use |
| US5106960A (en) * | 1980-03-28 | 1992-04-21 | Ciba-Geigy Corporation | Azo dyes and the production and use thereof |
-
1960
- 1960-03-02 GB GB7389/60A patent/GB868474A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2195663A1 (en) * | 1972-08-12 | 1974-03-08 | Bayer Ag | |
| US4055557A (en) * | 1972-08-12 | 1977-10-25 | Bayer Aktiengesellschaft | Sulfonamidobenzene-azo-aminopyrazole dyestuffs |
| US5106960A (en) * | 1980-03-28 | 1992-04-21 | Ciba-Geigy Corporation | Azo dyes and the production and use thereof |
| EP0102325A1 (en) * | 1982-08-04 | 1984-03-07 | Ciba-Geigy Ag | Monoazo dyestuffs, their preparation and their use |
| JPS5962667A (en) * | 1982-08-04 | 1984-04-10 | チバ−ガイギ・アクチエンゲゼルシヤフト | Monoazo dye, manufacture and use |
| US4918183A (en) * | 1982-08-04 | 1990-04-17 | Ciba-Geigy Corporation | Monoazo dyes, process for their preparation, and the use thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3907769A (en) | Azo compounds containing a 2,6-diaminopyridine coupler component | |
| GB1033266A (en) | Improvements relating to mono-and dis-azo dispersion dyestuffs and their use | |
| GB868474A (en) | Improvements relating to monoazo-pyrazole dyestuffs and their use | |
| GB1199243A (en) | Azo Dyestuffs and process for their production | |
| GB955085A (en) | Improvements relating to monoazo aminopyrazole dyestuffs and their use | |
| GB984802A (en) | New azo dyestuffs containing unsaturated carboxylic acid amide groups | |
| GB1061268A (en) | New water-insoluble azo dyestuffs | |
| GB977472A (en) | New monoazo compounds containing halogeno-triazinylamino groups | |
| GB1019774A (en) | Process for the production of anthraquinone dyestuffs | |
| GB1048250A (en) | New water-insoluble monoazo dyestuffs | |
| GB1117747A (en) | Water-soluble mono and disazo dyestuffs and processes for their manufacture | |
| GB878129A (en) | Improvements relating to monoazo dyestuffs derived from diphenyl ether and their use | |
| US3565884A (en) | Disperse monoazo dyes derived from 3-aminodiphenylene oxides | |
| GB1264071A (en) | ||
| GB885814A (en) | Water-soluble dyestuffs containing unsaturated carboxylic acid residues | |
| GB995368A (en) | Improvements relating to disazo dyestuffs and their use | |
| US2134038A (en) | Monoazo dyestuffs | |
| GB993594A (en) | Improvements in or relating to dyestuffs comprising anthraquinonyl and azo dye moieties | |
| GB957414A (en) | Benzene monoazo dyestuffs | |
| GB917725A (en) | Azo dyestuffs | |
| GB832285A (en) | Monoazo dyestuffs containing amidino groups | |
| GB2005292A (en) | Azo dyes | |
| GB1012239A (en) | New disperse dyestuffs of the benzene-azo-benzene series | |
| GB928675A (en) | New monoazo dyes containing 3-chlorotetrahydrofuryl-(2)-oxy groups and their manufacture and use | |
| GB1518842A (en) | Disperse monoazo dyestuffs |