DE69324721T2 - Polyzyklische Farbstoffe - Google Patents
Polyzyklische FarbstoffeInfo
- Publication number
- DE69324721T2 DE69324721T2 DE69324721T DE69324721T DE69324721T2 DE 69324721 T2 DE69324721 T2 DE 69324721T2 DE 69324721 T DE69324721 T DE 69324721T DE 69324721 T DE69324721 T DE 69324721T DE 69324721 T2 DE69324721 T2 DE 69324721T2
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- alkoxy
- ring
- substituted
- formula
- 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 - Fee Related
Links
- 125000003367 polycyclic group Chemical group 0.000 title claims description 7
- 239000000975 dye Substances 0.000 title description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical compound OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- BRWDHRZYOYDXTG-UHFFFAOYSA-N 5-hydroxy-3-phenyl-3h-1-benzofuran-2-one Chemical compound C12=CC(O)=CC=C2OC(=O)C1C1=CC=CC=C1 BRWDHRZYOYDXTG-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000001117 sulphuric acid Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 2
- QJQZRLXDLORINA-UHFFFAOYSA-N 2-cyclohexylethanol Chemical compound OCCC1CCCCC1 QJQZRLXDLORINA-UHFFFAOYSA-N 0.000 description 2
- CLYAQFSQLQTVNO-UHFFFAOYSA-N 3-cyclohexylpropan-1-ol Chemical compound OCCCC1CCCCC1 CLYAQFSQLQTVNO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- -1 alkyl radicals Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 229960002510 mandelic acid Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 description 1
- ISWSIWMERMANOR-UHFFFAOYSA-N 2-[4-(carboxymethoxy)phenyl]-2-hydroxyacetic acid Chemical compound OC(=O)C(O)C1=CC=C(OCC(O)=O)C=C1 ISWSIWMERMANOR-UHFFFAOYSA-N 0.000 description 1
- UBHMYNPCDNGWBM-UHFFFAOYSA-N 2-hydroxy-2-(4-propoxyphenyl)acetic acid Chemical compound CCCOC1=CC=C(C(O)C(O)=O)C=C1 UBHMYNPCDNGWBM-UHFFFAOYSA-N 0.000 description 1
- FKGJKJMSGFXIFA-UHFFFAOYSA-N 3-cyclohexylpropyl methanesulfonate Chemical compound CS(=O)(=O)OCCCC1CCCCC1 FKGJKJMSGFXIFA-UHFFFAOYSA-N 0.000 description 1
- ZUJQPYHJGXSZON-UHFFFAOYSA-N 5-hydroxy-3-(4-propoxyphenyl)-3h-1-benzofuran-2-one Chemical compound C1=CC(OCCC)=CC=C1C1C2=CC(O)=CC=C2OC1=O ZUJQPYHJGXSZON-UHFFFAOYSA-N 0.000 description 1
- ONALDONXJIPGKM-UHFFFAOYSA-N 5-hydroxy-3-(4-propoxyphenyl)-4h-1-benzofuran-2-one Chemical compound C1=CC(OCCC)=CC=C1C(C(O1)=O)=C2C1=CC=C(O)C2 ONALDONXJIPGKM-UHFFFAOYSA-N 0.000 description 1
- 239000004160 Ammonium persulphate Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- 235000019395 ammonium persulphate Nutrition 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929204904A GB9204904D0 (en) | 1992-03-06 | 1992-03-06 | Polycyclic dyes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69324721D1 DE69324721D1 (de) | 1999-06-10 |
| DE69324721T2 true DE69324721T2 (de) | 1999-11-11 |
Family
ID=10711626
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69324721T Expired - Fee Related DE69324721T2 (de) | 1992-03-06 | 1993-02-16 | Polyzyklische Farbstoffe |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5319109A (en:Method) |
| EP (1) | EP0559345B1 (en:Method) |
| JP (1) | JP3359685B2 (en:Method) |
| KR (1) | KR100248295B1 (en:Method) |
| DE (1) | DE69324721T2 (en:Method) |
| GB (2) | GB9204904D0 (en:Method) |
| TW (1) | TW274557B (en:Method) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0024440D0 (en) * | 2000-10-05 | 2000-11-22 | Basf Ag | Polycyclic dyes |
| CN102391274B (zh) * | 2011-09-23 | 2013-12-11 | 杭州福莱蒽特精细化工有限公司 | 一种不对称型苯并二呋喃酮类化合物的合成方法 |
| CN102924961B (zh) * | 2012-11-20 | 2014-03-26 | 江苏德旺化工工业有限公司 | 一种分散红的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8429169D0 (en) * | 1983-12-16 | 1984-12-27 | Ici Plc | Hetero-polycyclic aromatic compound |
| GB8823158D0 (en) * | 1988-10-03 | 1988-11-09 | Ici Plc | Polycyclic dyes |
| JP2900509B2 (ja) * | 1989-05-11 | 1999-06-02 | 住友化学工業株式会社 | 複素環式化合物およびそれを用いて疎水性繊維材料を染色または捺染する方法 |
-
1992
- 1992-03-06 GB GB929204904A patent/GB9204904D0/en active Pending
-
1993
- 1993-02-15 GB GB939303015A patent/GB9303015D0/en active Pending
- 1993-02-16 EP EP93301096A patent/EP0559345B1/en not_active Expired - Lifetime
- 1993-02-16 DE DE69324721T patent/DE69324721T2/de not_active Expired - Fee Related
- 1993-02-19 TW TW082101184A patent/TW274557B/zh active
- 1993-03-03 US US08/025,654 patent/US5319109A/en not_active Expired - Fee Related
- 1993-03-04 JP JP04348593A patent/JP3359685B2/ja not_active Expired - Fee Related
- 1993-03-06 KR KR1019930003396A patent/KR100248295B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR100248295B1 (ko) | 2000-03-15 |
| DE69324721D1 (de) | 1999-06-10 |
| KR930019771A (ko) | 1993-10-18 |
| TW274557B (en:Method) | 1996-04-21 |
| EP0559345B1 (en) | 1999-05-06 |
| GB9303015D0 (en) | 1993-03-31 |
| GB9204904D0 (en) | 1992-04-22 |
| US5319109A (en) | 1994-06-07 |
| JPH06128499A (ja) | 1994-05-10 |
| JP3359685B2 (ja) | 2002-12-24 |
| EP0559345A1 (en) | 1993-09-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1098125B (de) | Verfahren zur Herstellung von fluoreszierenden Verbindungen | |
| DE68920393T2 (de) | Polycyclische Farbstoffe. | |
| EP0252406A2 (de) | Verfahren zur Herstellung polycyclischer Verbindungen | |
| DE1443877C3 (en:Method) | ||
| EP0014344A1 (de) | Cumarinverbindungen, Verfahren zu ihrer Herstellung und deren Verwendung als Weisstöner und Laserfarbstoffe | |
| DE69703340T2 (de) | Heterozyklische monoazofarbstoffe | |
| DE69324721T2 (de) | Polyzyklische Farbstoffe | |
| EP0193885A1 (de) | Thiophenderivate | |
| DE1069313B (en:Method) | ||
| DE2736785A1 (de) | Neue dispersionsazofarbstoffe, verfahren zu ihrer herstellung sowie deren verwendung zum faerben oder bedrucken von synthetischen fasermaterialien | |
| DE2134518B2 (de) | Verfahren zur Herstellung von Verbindungen der Benzothioxanthenreihe | |
| DE2129565A1 (de) | Fluoreszierende Farbstoffe | |
| DE2262794A1 (de) | Styrylfarbstoffe und verfahren zu ihrer herstellung | |
| DE1225326B (de) | Verfahren zur Herstellung von Farbstoffen | |
| DE1519468A1 (de) | 3-Pyrazolyl-7-aryltriazolyl-cumarinverbindungen | |
| EP0095638B1 (de) | 2,6-Dicyananiline | |
| AT238212B (de) | Verfahren zur Herstellung von neuen 3-Aryl-4-halogen-pyridazonen-(6) | |
| EP0198206A1 (de) | Azofarbstoffe | |
| DE2357442C3 (de) | Naphtholactamfarbstoffe und deren Verwendung | |
| DE2306843B2 (de) | In wasser schwer loesliche cumarinverbindungen, ihre herstellung und verwendung | |
| DE1028718B (de) | Verfahren zur Herstellung von Cyanin- und Styryl-Farbstoffen | |
| CH624980A5 (en:Method) | ||
| DE1296722B (de) | Dioxoindanylchinolylbenthiazole, deren Herstellung und Verwendung als substantive Farbstoffe | |
| DE1769789C3 (de) | Gemische aus Chinophthalonfarbstoffen, deren Herstellung und Verwendung | |
| EP0169459A2 (de) | Azofarbstoffe |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |