GB951105A - Improvements in and relating to new azo dyestuffs - Google Patents
Improvements in and relating to new azo dyestuffsInfo
- Publication number
- GB951105A GB951105A GB2310760A GB2310760A GB951105A GB 951105 A GB951105 A GB 951105A GB 2310760 A GB2310760 A GB 2310760A GB 2310760 A GB2310760 A GB 2310760A GB 951105 A GB951105 A GB 951105A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyrazolone
- methyl
- dyestuff
- phenyl
- aniline
- 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 5
- 125000003118 aryl group Chemical group 0.000 abstract 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 abstract 1
- NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 abstract 1
- OXRSFHYBIRFJSF-UHFFFAOYSA-N 3-phenyl-1,4-dihydropyrazol-5-one Chemical compound N1C(=O)CC(C=2C=CC=CC=2)=N1 OXRSFHYBIRFJSF-UHFFFAOYSA-N 0.000 abstract 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 abstract 1
- FGCPAXRNQIOISG-UHFFFAOYSA-N ethyl 5-oxo-1,2-dihydropyrazole-3-carboxylate Chemical compound CCOC(=O)C=1C=C(O)NN=1 FGCPAXRNQIOISG-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 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
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 abstract 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical class ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 abstract 1
- 150000004993 o-toluidines Chemical class 0.000 abstract 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical class COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 abstract 1
- 150000004995 p-toluidines Chemical class 0.000 abstract 1
- 229920002239 polyacrylonitrile Polymers 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000003381 solubilizing effect Effects 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000001256 steam distillation Methods 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 0.000 abstract 1
- 239000011592 zinc chloride Substances 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
- C09B44/00—Azo dyes containing onium groups
- C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
- C09B44/14—1,2-Diazoles or hydrogenated 1,2-diazoles ; Pyrazolium; Indazolium
-
- 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 azo dyestuffs of formula <FORM:0951105/C3/1> wherein A is an anionic radical, R is the residue of a diazotizable amine free from solubilizing groups, R1 is hydrogen or an aryl group and R2 is an alkyl, aryl or alkoxycarbonyl group. The dyestuffs are prepared by alkylation of a suitable monoazo dyestuff. They are used to dye polyacrylonitrile fibres in yellow-green to red shades. In examples, the dyestuff aniline --> 3-methyl-5-pyrazolone is refluxed in chlorobenzene with dimethyl sulphate or methyl paratoluenesulphonate, the solvent is removed by steam distillation, the dyestuff solution filtered and the dyestuff precipitated by the addition of zinc chloride and salt. In further examples, additional components specified are o- and p-toluidines, m- and p-xylidines, the chloroanilines, o- and p-anisidines, o-nitroaniline, 4-nitro-2-methyl- or -methoxy-aniline, 2:5-dichloroaniline and b -naphthylamine; 3-ethoxycarbonyl - 5 - pyrazolone, 3 - phenyl - 5 - pyrazolone and 1-phenyl-3-methyl-5-pyrazolone.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR799016A FR1238392A (en) | 1959-07-01 | 1959-07-01 | New basic dyes and their application to the dyeing of polyacrylonitrile-based polymerizates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB951105A true GB951105A (en) | 1964-03-04 |
Family
ID=8716668
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2310760A Expired GB951105A (en) | 1959-07-01 | 1960-07-01 | Improvements in and relating to new azo dyestuffs |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH387196A (en) |
| FR (1) | FR1238392A (en) |
| GB (1) | GB951105A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH391145A (en) * | 1961-05-25 | 1965-04-30 | Geigy Ag J R | Process for the preparation of water-soluble color salts of azo dyes |
-
1959
- 1959-07-01 FR FR799016A patent/FR1238392A/en not_active Expired
-
1960
- 1960-06-15 CH CH681560A patent/CH387196A/en unknown
- 1960-07-01 GB GB2310760A patent/GB951105A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1238392A (en) | 1960-08-12 |
| CH387196A (en) | 1965-01-31 |
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