GB1112875A - Azo dyestuffs - Google Patents
Azo dyestuffsInfo
- Publication number
- GB1112875A GB1112875A GB4405266A GB4405266A GB1112875A GB 1112875 A GB1112875 A GB 1112875A GB 4405266 A GB4405266 A GB 4405266A GB 4405266 A GB4405266 A GB 4405266A GB 1112875 A GB1112875 A GB 1112875A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- substituted
- alkyl
- carboxylic acid
- appropriate
- 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
- -1 carboxylic acid ester radical Chemical class 0.000 abstract 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 abstract 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract 2
- 229910052736 halogen Chemical group 0.000 abstract 2
- 150000002367 halogens Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 239000000987 azo dye Substances 0.000 abstract 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 abstract 1
- 125000002843 carboxylic acid group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000004966 cyanoalkyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical group [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 239000010985 leather Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 abstract 1
- 239000004627 regenerated cellulose Substances 0.000 abstract 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical group NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 abstract 1
- 229940124530 sulfonamide Drugs 0.000 abstract 1
- 125000001174 sulfone group Chemical group 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 150000003568 thioethers Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- 210000002268 wool Anatomy 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/021—Disazo dyes characterised by two coupling components of the same type
- C09B35/03—Disazo dyes characterised by two coupling components of the same type in which the coupling component is a heterocyclic compound
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention comprises azo dyestuffs of the general formula <FORM:1112875/C4-C5/1> wherein A is an aromatic-carbocyclic or -heterocyclic radical or a copper phthalo-cyanine residue (Cu-Pc), R is H, alkyl, aralkyl, aryl, or carboxylic acid ester radical, R1 is C2-C10 straight or branched chain alkylene radical which may be substituted, R2 is H or C1-C4 alkyl radical, R3 is C1-C4 alkyl or alkenyl radical, n is 1 or 2 and when A is CuPc n is 1, 2, 3 or 4. R1, which is preferably ethylene or propylene, may be substituted by aryl, cycloalkyl, ether, thioether or halogen and A is preferably a benzene, naphthalene, thiazole, benzothiazole, imidazole or benzimidazole radical which may be substituted by sulphonic or carboxylic acid groups, sulphonamide, sulphone, carboxylic acid ester, nitro, substituted or acylated amino groups, cyano, halogen, trifluoromethyl, alkyl, alkoxy, cyanoalkyl, cyanalkoxy or further azo groups. They are prepared by (a) diazotizing an appropriate aromatic-carbocyclic or heterocyclic or CuPc diazo compound with an appropriate pyrazolone coupling component or (b) reacting an appropriate azo dye containing an -R1-OH group in the 1-pyrazolone position with a compound OCN-CH(R2)-OR3 in an organic solvent which is inert to isocyanates. The dyes give yellow, orange, red and green shades on wool, silk, leather and synthetic polyamides, natural or regenerated cellulose at elevated temperatures.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0047923 | 1965-12-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1112875A true GB1112875A (en) | 1968-05-08 |
Family
ID=7101920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4405266A Expired GB1112875A (en) | 1965-12-15 | 1966-10-03 | Azo dyestuffs |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE690912A (en) |
| CH (1) | CH470460A (en) |
| DE (1) | DE1544550A1 (en) |
| FR (1) | FR1505719A (en) |
| GB (1) | GB1112875A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4118186A (en) | 1976-05-13 | 1978-10-03 | Hoechst Aktiengesellschaft | Process for the fixation of organic dyestuffs on materials having a fibrous structure |
| US4201547A (en) | 1977-03-22 | 1980-05-06 | Hoechst Aktiengesellschaft | Process for the preparation of azo dyestuffs on fiber materials consisting of, or containing, cellulose fibers |
-
1965
- 1965-12-15 DE DE19651544550 patent/DE1544550A1/en active Pending
-
1966
- 1966-09-08 CH CH1299366A patent/CH470460A/en not_active IP Right Cessation
- 1966-10-03 GB GB4405266A patent/GB1112875A/en not_active Expired
- 1966-12-08 BE BE690912D patent/BE690912A/xx unknown
- 1966-12-15 FR FR87617A patent/FR1505719A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4118186A (en) | 1976-05-13 | 1978-10-03 | Hoechst Aktiengesellschaft | Process for the fixation of organic dyestuffs on materials having a fibrous structure |
| US4201547A (en) | 1977-03-22 | 1980-05-06 | Hoechst Aktiengesellschaft | Process for the preparation of azo dyestuffs on fiber materials consisting of, or containing, cellulose fibers |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1505719A (en) | 1967-12-15 |
| CH470460A (en) | 1969-03-31 |
| DE1544550A1 (en) | 1970-05-21 |
| BE690912A (en) | 1967-05-16 |
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