GB813906A - New mono-azo dyes - Google Patents
New mono-azo dyesInfo
- Publication number
- GB813906A GB813906A GB23935/55A GB2393555A GB813906A GB 813906 A GB813906 A GB 813906A GB 23935/55 A GB23935/55 A GB 23935/55A GB 2393555 A GB2393555 A GB 2393555A GB 813906 A GB813906 A GB 813906A
- Authority
- GB
- United Kingdom
- Prior art keywords
- nitro
- atom
- dyestuffs
- aniline
- hydroxyethyl
- 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
- 239000000987 azo dye Substances 0.000 title 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 title 1
- 238000005859 coupling reaction Methods 0.000 abstract 4
- 239000000975 dye Substances 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- 230000008878 coupling Effects 0.000 abstract 3
- 238000010168 coupling process Methods 0.000 abstract 3
- -1 cresidines Chemical class 0.000 abstract 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 abstract 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 2
- 229920000297 Rayon Polymers 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 150000004982 aromatic amines Chemical class 0.000 abstract 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical class C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 abstract 1
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical class NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 abstract 1
- YZOXPLQWARQVEJ-UHFFFAOYSA-N 2-methylsulfonyl-1,3-benzothiazole Chemical class C1=CC=C2SC(S(=O)(=O)C)=NC2=C1 YZOXPLQWARQVEJ-UHFFFAOYSA-N 0.000 abstract 1
- FENJKTQEFUPECW-UHFFFAOYSA-N 3-anilinopropanenitrile Chemical class N#CCCNC1=CC=CC=C1 FENJKTQEFUPECW-UHFFFAOYSA-N 0.000 abstract 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- 229910006095 SO2F Inorganic materials 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 229920002301 cellulose acetate Polymers 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 150000008049 diazo compounds Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 150000005002 naphthylamines Chemical class 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 150000004992 toluidines 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
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Coupling components for dyestuff manufacture (see Group IV (c)) of formula <FORM:0813906/IV (b)/1> where R2 is an acyl residue of an aliphatic carboxylic acid in which the O atom is attached to the b C atom of the N ethyl substituent and X is H or a non-reactive substituent which does not interfere with the initial formation of dyestuff during the coupling reaction may be made by acylating the corresponding N-b -hydroxyethyl-N-a -cyanoethylaniline. A preferred component is made by reacting N-b -hydroxyethyl-N-b -cyanoethyl-aniline with acetic anhydride at 125-30 DEG C. for 3 hours. Other components mentioned are the corresponding propionate and butyrate.ALSO:The invention comprises dyestuffs of formula <FORM:0813906/IV (c)/1> where R1 is the residue of an aromatic amine excluding an aromatic amine having an -SO2F group in the 2-position, or a benzothiazole, R2 is an acyl residue of an aliphatic carboxylic acid in which the O atom is attached to the b C atom of the N ethyl substituent and X is H or a non-reactive substituent on the benzene nucleus which does not interfere with the initial formation of the dyestuff. They may be made by coupling appropriate diazo compounds with the required acylated cyanoethylanilines. Indicated amines are aniline and its nitro and chloro derivatives, toluidines, phenetidine, cresidines, naphthylamines and amino benzothiazoles. The dyestuffs dye fibres of cellulose acetate, synthetic polyamides, polyesters and acrylonitrile copolymers. In examples, dyestuffs are made which colour cellulose acetate and acetate rayon fibres in red and orange shades the dyestuffs being prepared from the following amines: 4-nitro-, 2,4-dinitro- and 2-chlor-4-nitro-anilines and 2-amino-6-methyl-, methoxy-, chloro-, nitro- and methyl-sulphonyl-benzothiazoles and the following coupling components: the acetate, propionate and butyrate of N - b - hydroxyethyl - N - b - cyanoethyl - aniline. Specification 744,877 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US813906XA | 1954-08-19 | 1954-08-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB813906A true GB813906A (en) | 1959-05-27 |
Family
ID=22163834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23935/55A Expired GB813906A (en) | 1954-08-19 | 1955-08-19 | New mono-azo dyes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB813906A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1219608B (en) * | 1960-06-10 | 1966-06-23 | Sandoz Ag | Process for the preparation of water-insoluble monoazo dyes |
| FR2013236A1 (en) * | 1968-07-19 | 1970-03-27 | Basf Ag | |
| US4968318A (en) * | 1988-12-28 | 1990-11-06 | Bayer Aktiengesellschaft | Red mixtures of disperse azo dyestuffs |
-
1955
- 1955-08-19 GB GB23935/55A patent/GB813906A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1219608B (en) * | 1960-06-10 | 1966-06-23 | Sandoz Ag | Process for the preparation of water-insoluble monoazo dyes |
| FR2013236A1 (en) * | 1968-07-19 | 1970-03-27 | Basf Ag | |
| US4968318A (en) * | 1988-12-28 | 1990-11-06 | Bayer Aktiengesellschaft | Red mixtures of disperse azo dyestuffs |
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