DE60302472T2 - Oxidationsverfahren zur herstellung von chinacridonpigmenten - Google Patents
Oxidationsverfahren zur herstellung von chinacridonpigmenten Download PDFInfo
- Publication number
- DE60302472T2 DE60302472T2 DE60302472T DE60302472T DE60302472T2 DE 60302472 T2 DE60302472 T2 DE 60302472T2 DE 60302472 T DE60302472 T DE 60302472T DE 60302472 T DE60302472 T DE 60302472T DE 60302472 T2 DE60302472 T2 DE 60302472T2
- Authority
- DE
- Germany
- Prior art keywords
- quinacridone
- dihydroquinacridone
- weight
- salt
- dichloroquinacridone
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 48
- 239000000049 pigment Substances 0.000 title claims abstract description 48
- 230000008569 process Effects 0.000 title claims abstract description 17
- 238000007254 oxidation reaction Methods 0.000 title claims description 35
- 230000003647 oxidation Effects 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 title claims description 7
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 claims abstract description 59
- SNDAOXYSCAWUFQ-UHFFFAOYSA-N 5,6,12,13-tetrahydroquinolino[2,3-b]acridine-7,14-dione Chemical class N1C2=CC=CC=C2C(=O)C2=C1CC(C(=O)C1=CC=CC=C1N1)=C1C2 SNDAOXYSCAWUFQ-UHFFFAOYSA-N 0.000 claims abstract description 46
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 46
- 239000003054 catalyst Substances 0.000 claims abstract description 27
- 230000001590 oxidative effect Effects 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- XPZQBGDNVOHQIS-UHFFFAOYSA-N 2,9-dichloro-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione Chemical compound N1C2=CC=C(Cl)C=C2C(=O)C2=C1C=C(C(=O)C=1C(=CC=C(C=1)Cl)N1)C1=C2 XPZQBGDNVOHQIS-UHFFFAOYSA-N 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- 239000002585 base Substances 0.000 claims description 18
- -1 alkali metal salt Chemical class 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000002245 particle Substances 0.000 claims description 11
- 239000012429 reaction media Substances 0.000 claims description 11
- TXWSZJSDZKWQAU-UHFFFAOYSA-N 2,9-dimethyl-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione Chemical compound N1C2=CC=C(C)C=C2C(=O)C2=C1C=C(C(=O)C=1C(=CC=C(C=1)C)N1)C1=C2 TXWSZJSDZKWQAU-UHFFFAOYSA-N 0.000 claims description 9
- 238000010992 reflux Methods 0.000 claims description 9
- WKLOSXKZASUWLB-UHFFFAOYSA-N 2,9-dimethoxy-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione Chemical compound N1C2=CC=C(OC)C=C2C(=O)C2=C1C=C(C(=O)C=1C(=CC=C(C=1)OC)N1)C1=C2 WKLOSXKZASUWLB-UHFFFAOYSA-N 0.000 claims description 8
- 239000006104 solid solution Substances 0.000 claims description 8
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- 239000003966 growth inhibitor Substances 0.000 claims description 6
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 5
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- BFEJTCHFLJECJN-UHFFFAOYSA-N 4,11-Dichloro-5,12-dihydroquino[2,3-b]acridine-7,14-dione Chemical compound N1C2=C(Cl)C=CC=C2C(=O)C2=C1C=C(C(C=1C=CC=C(C=1N1)Cl)=O)C1=C2 BFEJTCHFLJECJN-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- YEIYQKSCDPOVNO-UHFFFAOYSA-N 5,8,9,12-tetrahydroquinolino[2,3-b]acridine-7,14-dione Chemical compound N1C2=CC=CC=C2C(=O)C(C=C2N3)=C1C=C2C(=O)C1=C3C=CCC1 YEIYQKSCDPOVNO-UHFFFAOYSA-N 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- VTGOVLRDTGCTMT-UHFFFAOYSA-N 2,9-difluoro-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione Chemical compound N1C2=CC=C(F)C=C2C(=O)C2=C1C=C(C(=O)C=1C(=CC=C(C=1)F)N1)C1=C2 VTGOVLRDTGCTMT-UHFFFAOYSA-N 0.000 claims description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
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- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 1
- KKQCQCXUVZBOCL-UHFFFAOYSA-N 1h-pyrrole-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CN1 KKQCQCXUVZBOCL-UHFFFAOYSA-N 0.000 claims 1
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- 239000003377 acid catalyst Substances 0.000 claims 1
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- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 abstract description 13
- OKONMFPEKSWGEU-UHFFFAOYSA-N 9,10-dioxoanthracene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 OKONMFPEKSWGEU-UHFFFAOYSA-N 0.000 abstract description 6
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229920005989 resin Chemical class 0.000 description 10
- 239000011347 resin Chemical class 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
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- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 6
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- KSLLMGLKCVSKFF-UHFFFAOYSA-N 5,12-dihydroquinolino[2,3-b]acridine-6,7,13,14-tetrone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C(=O)C(C(=O)C1=CC=CC=C1N1)=C1C2=O KSLLMGLKCVSKFF-UHFFFAOYSA-N 0.000 description 4
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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- 150000002828 nitro derivatives Chemical class 0.000 description 1
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- 239000004014 plasticizer Chemical class 0.000 description 1
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- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
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- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920001291 polyvinyl halide Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
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- 159000000001 potassium salts Chemical class 0.000 description 1
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- GGCZERPQGJTIQP-UHFFFAOYSA-M sodium 2-anthraquinonesulfonate Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)[O-])=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-M 0.000 description 1
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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
- C09B48/00—Quinacridones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0025—Crystal modifications; Special X-ray patterns
- C09B67/0027—Crystal modifications; Special X-ray patterns of quinacridones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Compounds Of Unknown Constitution (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39637702P | 2002-07-17 | 2002-07-17 | |
| US396377P | 2002-07-17 | ||
| PCT/EP2003/007337 WO2004007623A1 (en) | 2002-07-17 | 2003-07-08 | Oxidation process for preparing quinacridone pigments |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60302472D1 DE60302472D1 (de) | 2005-12-29 |
| DE60302472T2 true DE60302472T2 (de) | 2006-04-13 |
Family
ID=30116019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60302472T Expired - Lifetime DE60302472T2 (de) | 2002-07-17 | 2003-07-08 | Oxidationsverfahren zur herstellung von chinacridonpigmenten |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7161007B2 (enExample) |
| EP (1) | EP1521809B1 (enExample) |
| JP (1) | JP4563804B2 (enExample) |
| KR (1) | KR101061456B1 (enExample) |
| CN (1) | CN100358949C (enExample) |
| AT (1) | ATE310773T1 (enExample) |
| AU (1) | AU2003250911A1 (enExample) |
| BR (1) | BR0312705A (enExample) |
| CA (1) | CA2489989A1 (enExample) |
| DE (1) | DE60302472T2 (enExample) |
| MX (1) | MX251590B (enExample) |
| WO (1) | WO2004007623A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6864371B2 (en) * | 2002-11-27 | 2005-03-08 | Ciba Specialty Chemicals Corporation | Preparation of beta quinacridone pigments |
| WO2004067642A1 (en) | 2003-01-28 | 2004-08-12 | Ciba Specialty Chemicals Holding Inc. | Synthesis of small particle size quinacridone of beta crystal phase |
| DE102004019415A1 (de) * | 2004-04-19 | 2005-11-03 | Röhm GmbH & Co. KG | Mischungen zur Herstellung transparenter Kunststoffe, transparente Kunststoffe sowie Verfahren zu deren Herstellung und Verwendung |
| WO2009132293A1 (en) | 2008-04-25 | 2009-10-29 | Sun Chemical Corporation | Novel crystal forms of quinacridones made from 2,9-dimethoxyquinacridone and 2,9-dichloroquinacridone |
| CN102585541A (zh) * | 2012-01-09 | 2012-07-18 | 浙江永泉化学有限公司 | 2，9-二甲基喹吖啶酮的制备方法 |
| CN105367454B (zh) * | 2015-11-10 | 2017-06-06 | 杭州百合科莱恩颜料有限公司 | 一种利用喹吖啶酮颜料副产物生产间氨基苯磺酸的方法 |
| CN105384652B (zh) * | 2015-11-27 | 2017-12-19 | 百合花集团股份有限公司 | 制备2,5‑二(取代)芳胺基对苯二酸的方法 |
| CN105348127A (zh) * | 2015-12-08 | 2016-02-24 | 温州金源化工有限公司 | 喹吖啶酮中间体的制备方法 |
| CN111019387A (zh) * | 2019-12-29 | 2020-04-17 | 河北彩客化学股份有限公司 | 一种2,9-二甲基喹吖啶酮紫红颜料的制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5502192A (en) | 1994-08-08 | 1996-03-26 | Ciba-Geigy Corporation | Process for the preparation of quinacridones from dihydroquinacridones in an aqueous medium |
| EP0806456B1 (en) | 1996-05-10 | 2001-07-25 | Ciba SC Holding AG | Oxidation process for preparing quinacridone pigments |
| EP0829523B1 (en) * | 1996-08-16 | 2001-09-12 | Ciba SC Holding AG | Oxidation process for preparing quinacridone pigments |
| DE69801302T2 (de) | 1997-08-01 | 2002-03-14 | Ciba Speciality Chemicals Holding Inc., Basel | Verfahren zur Herstellung fester Lösungen von Chinacridonen |
| US6031100A (en) * | 1997-09-18 | 2000-02-29 | Bayer Corporation | Microwave syntheses of quinacridones, 6,13-Dihydroquinacridones, and 6,13-quinacridonequinones |
| DE60026133T2 (de) * | 1999-02-02 | 2006-08-03 | Ciba Speciality Chemicals Holding Inc. | Verbindungen zur Kontrolle des Teilchenwachstums und /oder der Kristallphase von Pigmenten |
| US6264733B1 (en) * | 1999-02-02 | 2001-07-24 | Ciba Specialty Chemicals Corporation | Pigment particle growth and/or crystal phase directors |
| US6225472B1 (en) | 1999-02-02 | 2001-05-01 | Ciba Specialty Chemicals Corporation | 6,13-dihydroquinacridone derivatives |
| GB9920919D0 (en) * | 1999-09-03 | 1999-11-10 | Sb Pharmco Inc | Novel compound |
-
2003
- 2003-07-08 BR BR0312705-2A patent/BR0312705A/pt not_active Application Discontinuation
- 2003-07-08 US US10/517,412 patent/US7161007B2/en not_active Expired - Lifetime
- 2003-07-08 EP EP03763746A patent/EP1521809B1/en not_active Expired - Lifetime
- 2003-07-08 JP JP2004520524A patent/JP4563804B2/ja not_active Expired - Lifetime
- 2003-07-08 MX MXPA04012541 patent/MX251590B/es active IP Right Grant
- 2003-07-08 KR KR1020057000726A patent/KR101061456B1/ko not_active Expired - Lifetime
- 2003-07-08 CA CA002489989A patent/CA2489989A1/en not_active Abandoned
- 2003-07-08 AT AT03763746T patent/ATE310773T1/de not_active IP Right Cessation
- 2003-07-08 WO PCT/EP2003/007337 patent/WO2004007623A1/en not_active Ceased
- 2003-07-08 AU AU2003250911A patent/AU2003250911A1/en not_active Abandoned
- 2003-07-08 CN CNB038167816A patent/CN100358949C/zh not_active Expired - Lifetime
- 2003-07-08 DE DE60302472T patent/DE60302472T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR101061456B1 (ko) | 2011-09-02 |
| CN100358949C (zh) | 2008-01-02 |
| US20050176959A1 (en) | 2005-08-11 |
| CN1668708A (zh) | 2005-09-14 |
| EP1521809A1 (en) | 2005-04-13 |
| US7161007B2 (en) | 2007-01-09 |
| BR0312705A (pt) | 2005-04-26 |
| KR20050028027A (ko) | 2005-03-21 |
| ATE310773T1 (de) | 2005-12-15 |
| MXPA04012541A (es) | 2005-04-19 |
| MX251590B (es) | 2007-11-20 |
| DE60302472D1 (de) | 2005-12-29 |
| CA2489989A1 (en) | 2004-01-22 |
| EP1521809B1 (en) | 2005-11-23 |
| AU2003250911A1 (en) | 2004-02-02 |
| WO2004007623A1 (en) | 2004-01-22 |
| JP2005533144A (ja) | 2005-11-04 |
| JP4563804B2 (ja) | 2010-10-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8328 | Change in the person/name/address of the agent |
Representative=s name: PFENNING MEINIG & PARTNER GBR, 80339 MUENCHEN |
|
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: CIBA HOLDING INC., BASEL, CH |
|
| 8328 | Change in the person/name/address of the agent |
Representative=s name: MAIWALD PATENTANWALTSGESELLSCHAFT MBH, 80335 MUENC |