JP4369539B2 - キナクリドン固溶体の製造方法 - Google Patents
キナクリドン固溶体の製造方法 Download PDFInfo
- Publication number
- JP4369539B2 JP4369539B2 JP21494798A JP21494798A JP4369539B2 JP 4369539 B2 JP4369539 B2 JP 4369539B2 JP 21494798 A JP21494798 A JP 21494798A JP 21494798 A JP21494798 A JP 21494798A JP 4369539 B2 JP4369539 B2 JP 4369539B2
- Authority
- JP
- Japan
- Prior art keywords
- dihydroquinacridone
- quinacridone
- weight
- salt
- solid solution
- 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
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- 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 title claims description 90
- 239000006104 solid solution Substances 0.000 title claims description 52
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- SNDAOXYSCAWUFQ-UHFFFAOYSA-N 5,6,12,13-tetrahydroquinolino[2,3-b]acridine-7,14-dione Chemical compound N1C2=CC=CC=C2C(=O)C2=C1CC(C(=O)C1=CC=CC=C1N1)=C1C2 SNDAOXYSCAWUFQ-UHFFFAOYSA-N 0.000 claims description 119
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 64
- 239000000049 pigment Substances 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 44
- 239000002245 particle Substances 0.000 claims description 30
- 238000007254 oxidation reaction Methods 0.000 claims description 26
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 22
- -1 aromatic nitro compound Chemical class 0.000 claims description 22
- 239000002585 base Substances 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 21
- 230000003647 oxidation Effects 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 238000010992 reflux Methods 0.000 claims description 14
- 239000012429 reaction media Substances 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000007800 oxidant agent Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 230000001590 oxidative effect Effects 0.000 claims description 9
- 239000012071 phase Substances 0.000 claims description 9
- 239000013078 crystal Substances 0.000 claims description 7
- 239000007791 liquid phase Substances 0.000 claims description 7
- 239000003966 growth inhibitor Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- 239000002002 slurry Substances 0.000 claims description 4
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 claims description 2
- HWTDMFJYBAURQR-UHFFFAOYSA-N 80-82-0 Chemical class OS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O HWTDMFJYBAURQR-UHFFFAOYSA-N 0.000 claims description 2
- 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 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000003796 beauty Effects 0.000 claims 1
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- 238000002441 X-ray diffraction Methods 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
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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
- 239000007789 gas Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000001054 red pigment Substances 0.000 description 4
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- 238000005406 washing Methods 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000004129 EU approved improving agent Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 3
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- MMNWSHJJPDXKCH-UHFFFAOYSA-N 9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 MMNWSHJJPDXKCH-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 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 2
- 239000011230 binding agent Substances 0.000 description 2
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- 239000002270 dispersing agent Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical class CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
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- 239000012467 final product Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 230000002572 peristaltic effect Effects 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 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 2
- LJRGBERXYNQPJI-UHFFFAOYSA-M sodium;3-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 LJRGBERXYNQPJI-UHFFFAOYSA-M 0.000 description 2
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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- KKQCQCXUVZBOCL-UHFFFAOYSA-N 1h-pyrrole-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CN1 KKQCQCXUVZBOCL-UHFFFAOYSA-N 0.000 description 1
- ZJQZWNLKRBUEKX-UHFFFAOYSA-N 2,5-dianilinoterephthalic acid Chemical compound OC(=O)C=1C=C(NC=2C=CC=CC=2)C(C(=O)O)=CC=1NC1=CC=CC=C1 ZJQZWNLKRBUEKX-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
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- 239000011521 glass Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 150000005181 nitrobenzenes Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 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
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- VLCQZHSMCYCDJL-UHFFFAOYSA-N tribenuron methyl Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 VLCQZHSMCYCDJL-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
- 239000008096 xylene 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
- 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
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0034—Mixtures of two or more pigments or dyes of the same type
- C09B67/0036—Mixtures of quinacridones
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5452097P | 1997-08-01 | 1997-08-01 | |
| US60/054520 | 1997-08-01 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH11100522A JPH11100522A (ja) | 1999-04-13 |
| JPH11100522A5 JPH11100522A5 (enExample) | 2005-10-27 |
| JP4369539B2 true JP4369539B2 (ja) | 2009-11-25 |
Family
ID=21991661
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21494798A Expired - Fee Related JP4369539B2 (ja) | 1997-08-01 | 1998-07-30 | キナクリドン固溶体の製造方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6013127A (enExample) |
| EP (1) | EP0894832B1 (enExample) |
| JP (1) | JP4369539B2 (enExample) |
| KR (1) | KR100566838B1 (enExample) |
| CN (1) | CN1105154C (enExample) |
| BR (1) | BR9802832A (enExample) |
| CZ (1) | CZ240898A3 (enExample) |
| DE (1) | DE69801302T2 (enExample) |
| TW (1) | TW523530B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0208220A (pt) | 2001-03-22 | 2004-04-13 | Ciba Sc Holding Ag | Uso de compostos aromáticos como diretores de fase e redutores de tamanho de partìcula para pigmentos quinacridona |
| BR0312705A (pt) | 2002-07-17 | 2005-04-26 | Ciba Sc Holding Ag | Processo de oxidação para preparação de pigmentos de quinacridona |
| KR101082130B1 (ko) * | 2002-10-18 | 2011-11-09 | 이화이어 아이피 코포레이션 | 컬러 전계발광 디스플레이 |
| EP1457535B1 (en) * | 2002-11-01 | 2011-08-24 | Seiko Epson Corporation | Ink set, recording method, recording device, recording system, and recorded object |
| US6864371B2 (en) | 2002-11-27 | 2005-03-08 | Ciba Specialty Chemicals Corporation | Preparation of beta quinacridone pigments |
| WO2004063284A1 (en) * | 2003-01-14 | 2004-07-29 | Ciba Specialty Chemicals Holding Inc. | Oxidation process for preparing highly dispersible 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 |
| AU2004263664A1 (en) * | 2003-07-18 | 2005-02-17 | Ciba Specialty Chemicals Holding Inc. | Quinacridone pigment compositions comprising unsymmetrically substituted components |
| US11091615B2 (en) | 2014-11-20 | 2021-08-17 | Cytec Industries Inc. | Stabilizer compositions and methods for using same for protecting organic materials from UV light and thermal degradation |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3160510A (en) * | 1960-04-25 | 1964-12-08 | Du Pont | Quinacridone pigment compositions |
| FR1346126A (fr) * | 1963-01-31 | 1963-12-13 | Cassella Farbwerke Mainkur Ag | Procédé de préparation de quinacridones |
| US3748162A (en) * | 1971-03-19 | 1973-07-24 | Du Pont | Light stable quinacridonequinone yellow pigment |
| DE3834748A1 (de) * | 1988-10-12 | 1990-04-19 | Bayer Ag | Verfahren zur herstellung eines gegebenenfalls substituierten chinacridons |
| US5229515A (en) * | 1991-06-07 | 1993-07-20 | Ciba-Geigy Corporation | Process for preparing modified β-quinacridone pigment |
| US5223624A (en) * | 1991-08-22 | 1993-06-29 | Baebler Fridolin | Modified gamma-quinacridone pigment |
| 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 |
-
1998
- 1998-07-23 DE DE69801302T patent/DE69801302T2/de not_active Expired - Lifetime
- 1998-07-23 EP EP98810713A patent/EP0894832B1/en not_active Expired - Lifetime
- 1998-07-24 US US09/122,553 patent/US6013127A/en not_active Expired - Lifetime
- 1998-07-30 TW TW087112539A patent/TW523530B/zh not_active IP Right Cessation
- 1998-07-30 JP JP21494798A patent/JP4369539B2/ja not_active Expired - Fee Related
- 1998-07-30 CZ CZ982408A patent/CZ240898A3/cs unknown
- 1998-07-31 CN CN98116750A patent/CN1105154C/zh not_active Expired - Fee Related
- 1998-07-31 KR KR1019980031143A patent/KR100566838B1/ko not_active Expired - Fee Related
- 1998-08-03 BR BR9802832-4A patent/BR9802832A/pt not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE69801302D1 (de) | 2001-09-13 |
| EP0894832A3 (en) | 1999-02-10 |
| US6013127A (en) | 2000-01-11 |
| KR100566838B1 (ko) | 2006-05-25 |
| BR9802832A (pt) | 2000-05-09 |
| EP0894832A2 (en) | 1999-02-03 |
| DE69801302T2 (de) | 2002-03-14 |
| EP0894832B1 (en) | 2001-08-08 |
| KR19990023273A (ko) | 1999-03-25 |
| TW523530B (en) | 2003-03-11 |
| CZ240898A3 (cs) | 1999-03-17 |
| JPH11100522A (ja) | 1999-04-13 |
| CN1207402A (zh) | 1999-02-10 |
| CN1105154C (zh) | 2003-04-09 |
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