GB1600923A - Monoazo dyes based on dialkoxy-substituted acetoacetarylides as coupling components - Google Patents
Monoazo dyes based on dialkoxy-substituted acetoacetarylides as coupling components Download PDFInfo
- Publication number
- GB1600923A GB1600923A GB17961/78A GB1796178A GB1600923A GB 1600923 A GB1600923 A GB 1600923A GB 17961/78 A GB17961/78 A GB 17961/78A GB 1796178 A GB1796178 A GB 1796178A GB 1600923 A GB1600923 A GB 1600923A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- chlorine
- bromine
- general formula
- hydrogen
- 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
- 230000008878 coupling Effects 0.000 title claims description 10
- 238000010168 coupling process Methods 0.000 title claims description 10
- 238000005859 coupling reaction Methods 0.000 title claims description 10
- 239000000975 dye Substances 0.000 title description 6
- 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 description 3
- 239000000460 chlorine Substances 0.000 claims description 24
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 150000001989 diazonium salts Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000008199 coating composition Substances 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- -1 nitro, methyl Chemical group 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- 239000012463 white pigment Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 2
- 239000001060 yellow colorant Substances 0.000 description 2
- QMBANXLJKPZBTA-UHFFFAOYSA-N 2,4-dimethoxy-3-oxo-n-phenylbutanamide Chemical compound COCC(=O)C(OC)C(=O)NC1=CC=CC=C1 QMBANXLJKPZBTA-UHFFFAOYSA-N 0.000 description 1
- BEKMTRPOJAKFPZ-UHFFFAOYSA-N 2-(3-phenyl-1,2,4-oxadiazol-5-yl)aniline Chemical compound NC1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NO1 BEKMTRPOJAKFPZ-UHFFFAOYSA-N 0.000 description 1
- YLQDROQQHPYPHU-UHFFFAOYSA-N 4-chloro-2-(3-phenyl-1,2,4-oxadiazol-5-yl)aniline Chemical compound NC1=CC=C(Cl)C=C1C1=NC(C=2C=CC=CC=2)=NO1 YLQDROQQHPYPHU-UHFFFAOYSA-N 0.000 description 1
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 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
- C09B29/32—Monoazo dyes prepared by diazotising and coupling from coupling components containing a reactive methylene group
- C09B29/33—Aceto- or benzoylacetylarylides
- C09B29/335—Aceto- or benzoylacetylarylides free of acid groups
- C09B29/337—Carbocyclic arylides
-
- 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
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
- C09B29/0011—Monoazo dyes prepared by diazotising and coupling from diazotized anilines from diazotized anilines directly substituted by a heterocyclic ring (not condensed)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Coloring (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772720659 DE2720659A1 (de) | 1977-05-07 | 1977-05-07 | Pigmentfarbstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1600923A true GB1600923A (en) | 1981-10-21 |
Family
ID=6008352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17961/78A Expired GB1600923A (en) | 1977-05-07 | 1978-05-05 | Monoazo dyes based on dialkoxy-substituted acetoacetarylides as coupling components |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS53138433A (enrdf_load_stackoverflow) |
| BE (1) | BE866667A (enrdf_load_stackoverflow) |
| DE (1) | DE2720659A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2389663A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1600923A (enrdf_load_stackoverflow) |
| IT (1) | IT1094808B (enrdf_load_stackoverflow) |
| NL (1) | NL7804779A (enrdf_load_stackoverflow) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH611324A5 (enrdf_load_stackoverflow) * | 1974-04-09 | 1979-05-31 | Basf Ag | |
| AT350998B (de) * | 1976-03-18 | 1979-06-25 | Basf Ag | Farbstoffzubereitungen fuer cellulose und cellulosehaltiges textilmaterial |
-
1977
- 1977-05-07 DE DE19772720659 patent/DE2720659A1/de not_active Withdrawn
-
1978
- 1978-04-28 IT IT22882/78A patent/IT1094808B/it active
- 1978-05-03 FR FR7813074A patent/FR2389663A1/fr not_active Withdrawn
- 1978-05-03 BE BE187357A patent/BE866667A/xx unknown
- 1978-05-03 NL NL7804779A patent/NL7804779A/xx not_active Application Discontinuation
- 1978-05-04 JP JP5285478A patent/JPS53138433A/ja active Pending
- 1978-05-05 GB GB17961/78A patent/GB1600923A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2720659A1 (de) | 1978-11-09 |
| BE866667A (fr) | 1978-11-03 |
| IT1094808B (it) | 1985-08-10 |
| FR2389663A1 (enrdf_load_stackoverflow) | 1978-12-01 |
| NL7804779A (nl) | 1978-11-09 |
| JPS53138433A (en) | 1978-12-02 |
| IT7822882A0 (it) | 1978-04-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR20000016141A (ko) | 안료 조성물 | |
| GB1599812A (en) | Salts of 1:2-metal-complex dyes free from sulphonic acid groups processes for producing the salts and their use | |
| DE2023295A1 (en) | Water insoluble azo dyes for dyeing polyesters polyamides cellulose - esters and polypropylene | |
| GB1583109A (en) | Disazo dyes | |
| USRE27575E (en) | Water-insoluble benzimidazolone containing monoazo dyestuffs | |
| CA2497388A1 (en) | Mono azo dyes | |
| CA1135688A (en) | Disazo compounds, process for their manufacture and their use | |
| US3583970A (en) | Mono azo pyrazolyl containing dyestuffs | |
| JPH05202306A (ja) | 染料、その製造方法及びその用途 | |
| GB1600923A (en) | Monoazo dyes based on dialkoxy-substituted acetoacetarylides as coupling components | |
| JP3608813B2 (ja) | アゾ化合物およびその製法 | |
| DE2351294A1 (de) | Azopigmente | |
| US6756486B1 (en) | Non-migrating metallized disazo green shade yellow pigment | |
| EP0062200B1 (de) | Neue Disazofarbstoffe | |
| US4055559A (en) | Disazo pigment containing at least 2 chlorine atoms and process for their manufacture | |
| US5428136A (en) | Water-insoluble azo colorants having two azo groups and a 1,4-bis (acetoacetylamino) benzene coupling component | |
| CA1062702A (en) | Disazo dyes | |
| EP0036081A1 (de) | Azofarbstoffe sowie deren Herstellung und Verwendung zum Färben von Synthesefasern | |
| EP0074048A2 (de) | Farbstoffe mit Isochinolin-Kupplungskomponenten | |
| US3718640A (en) | Triazole azo pigments | |
| CA1045121A (en) | Disazo pigment and process for its manufacture | |
| DE2544568C3 (de) | Sulfonsäuregruppenfreie Azofarbstoffe, Verfahren zu ihrer Herstellung und deren Verwendung als Pigmente in Lacken, Druckfarben oder Kunststoffen | |
| DE2531776A1 (de) | Azopigmente mit einem phthalazonrest | |
| DE2424538A1 (de) | Azofarbstoffe mit einem phthalazonrest | |
| JPH09255886A (ja) | ジスアゾ顔料 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CSNS | Application of which complete specification have been accepted and published, but patent is not sealed |