JPS6241542B2 - - Google Patents
Info
- Publication number
- JPS6241542B2 JPS6241542B2 JP55029846A JP2984680A JPS6241542B2 JP S6241542 B2 JPS6241542 B2 JP S6241542B2 JP 55029846 A JP55029846 A JP 55029846A JP 2984680 A JP2984680 A JP 2984680A JP S6241542 B2 JPS6241542 B2 JP S6241542B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- dye
- substituted
- dye according
- 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
- 239000000049 pigment Substances 0.000 claims description 19
- -1 N-phenylcarbamoyl group Chemical group 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 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
- 239000002966 varnish Substances 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 239000000976 ink Substances 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229920003002 synthetic resin Polymers 0.000 claims description 4
- 239000000057 synthetic resin Substances 0.000 claims description 4
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 3
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 3
- 230000000485 pigmenting effect Effects 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 239000000975 dye Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- RZVCEPSDYHAHLX-UHFFFAOYSA-N 3-iminoisoindol-1-amine Chemical compound C1=CC=C2C(N)=NC(=N)C2=C1 RZVCEPSDYHAHLX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- MWUCSURZWUDISB-UHFFFAOYSA-N 2-(4-aminophenyl)isoindole-1,3-dione Chemical compound C1=CC(N)=CC=C1N1C(=O)C2=CC=CC=C2C1=O MWUCSURZWUDISB-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- OGAMRAQUAIMWKV-UHFFFAOYSA-N 2-(3-aminoisoindol-1-ylidene)-2-cyano-n-phenylacetamide Chemical compound C12=CC=CC=C2C(=N)NC1=C(C#N)C(=O)NC1=CC=CC=C1 OGAMRAQUAIMWKV-UHFFFAOYSA-N 0.000 description 1
- MTKKGHVQPVOXIL-UHFFFAOYSA-N 3h-isoindol-1-amine Chemical compound C1=CC=C2C(N)=NCC2=C1 MTKKGHVQPVOXIL-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000005236 alkanoylamino group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 1
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000005281 alkyl ureido group Chemical group 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000005239 aroylamino group Chemical group 0.000 description 1
- 125000005116 aryl carbamoyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 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
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000003950 cyclic amides Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 235000012438 extruded product Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical group N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/04—Isoindoline dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Detergent Compositions (AREA)
- Indole Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2909645A DE2909645A1 (de) | 1979-03-12 | 1979-03-12 | Schwerloesliche isoindolinfarbstoffe und deren verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55123654A JPS55123654A (en) | 1980-09-24 |
| JPS6241542B2 true JPS6241542B2 (US06815460-20041109-C00097.png) | 1987-09-03 |
Family
ID=6065149
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2984680A Granted JPS55123654A (en) | 1979-03-12 | 1980-03-11 | Hard soluble isoindoline coloring matter and its use |
Country Status (5)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63154230U (US06815460-20041109-C00097.png) * | 1987-03-31 | 1988-10-11 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0568497B1 (de) * | 1992-04-30 | 1999-07-07 | Ciba SC Holding AG | Chromogene Methylenpyrroline |
| DE4409902A1 (de) * | 1994-03-23 | 1995-09-28 | Basf Ag | Isoindolinazopigmente |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670748A1 (de) * | 1966-09-09 | 1973-05-30 | Bayer Ag | Verfahren zur herstellung neuer isoindolinderivate |
| FR1537299A (fr) * | 1966-09-09 | 1968-08-23 | Bayer Ag | Procédé de préparation de nouveaux dérivés de l'isoindoline |
| CH614457A5 (US06815460-20041109-C00097.png) * | 1975-04-11 | 1979-11-30 | Ciba Geigy Ag | |
| US4040882A (en) * | 1975-09-29 | 1977-08-09 | General Electric Company | Primer composition, composite and method for making the same |
-
1979
- 1979-03-12 DE DE2909645A patent/DE2909645A1/de not_active Withdrawn
-
1980
- 1980-03-07 US US06/128,153 patent/US4356123A/en not_active Expired - Lifetime
- 1980-03-07 EP EP80101163A patent/EP0015570B1/de not_active Expired
- 1980-03-07 DE DE8080101163T patent/DE3061390D1/de not_active Expired
- 1980-03-11 JP JP2984680A patent/JPS55123654A/ja active Granted
- 1980-03-11 AU AU56315/80A patent/AU532900B2/en not_active Ceased
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63154230U (US06815460-20041109-C00097.png) * | 1987-03-31 | 1988-10-11 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0015570B1 (de) | 1982-12-22 |
| DE3061390D1 (en) | 1983-01-27 |
| EP0015570A1 (de) | 1980-09-17 |
| AU532900B2 (en) | 1983-10-20 |
| AU5631580A (en) | 1980-09-18 |
| JPS55123654A (en) | 1980-09-24 |
| DE2909645A1 (de) | 1980-09-18 |
| US4356123A (en) | 1982-10-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5248774A (en) | Inner salts based on ammonium and sulfonate groups of perylene-3,4,9,10-tetracarboxylic and derivatives thereof | |
| US4262120A (en) | Isoindoline pigments | |
| DE2041999A1 (de) | Pigmentfarbstoffe | |
| US3891685A (en) | Azomethine copper complex dyes and process for their preparation | |
| US4480097A (en) | Isoindoline colorants | |
| US3979386A (en) | Iminoisoindoline pigments and processes for the preparation thereof | |
| US4666526A (en) | Azine pigments, processes for their preparation, and their use | |
| JPS644543B2 (US06815460-20041109-C00097.png) | ||
| JPS6241542B2 (US06815460-20041109-C00097.png) | ||
| US4525591A (en) | 2,4-Dioxotetrahydropyrimido-(1,2-a)-benzimidazole substituted isoindoline dyes and their use | |
| EP0035139B1 (de) | Isoindolinfarbstoffe und deren Verwendung | |
| US4259488A (en) | Bis-isoindoline pigments | |
| US4052410A (en) | Iminoisoindoline pigments | |
| JPH07747B2 (ja) | ビス―イソインドリン顔料及び合成樹脂、印刷インキ又はワニスの着色法 | |
| US4340735A (en) | Isoindoline colorants | |
| US4725685A (en) | Novel isoindoline compounds, their metal complexes and their use as pigments | |
| JPS6331515B2 (US06815460-20041109-C00097.png) | ||
| US3994921A (en) | Iminoisoindolenine pigments, process for their manufacture and their use | |
| US4271309A (en) | Isoindoline colorants | |
| US5756691A (en) | Water--insoluble azo colorants based on N-acetoacetyldehydrothiotoluidine | |
| DE3311375A1 (de) | Isoindolinfarbstoffe und deren verwendung | |
| EP0043010B1 (de) | Pigmentfarbstoffe | |
| DE3111650A1 (de) | "neue isolindolinfarbstoffe und deren verwendung" | |
| EP0017003A1 (de) | Isoindolinfarbstoffe und deren Verwendung als Pigmente | |
| EP0025473A1 (de) | Pigmentfarbstoffe der Monoazo-2,3-oxynaphthoesäurearylidreihe und deren Verwendung zum Färben von Druckfarben, Lacken oder Kunststoffen |
