DE69715130T2 - Einarbeitung von Chinacridonderivaten während des Chinacridonherstellungsverfahrens - Google Patents
Einarbeitung von Chinacridonderivaten während des ChinacridonherstellungsverfahrensInfo
- Publication number
- DE69715130T2 DE69715130T2 DE69715130T DE69715130T DE69715130T2 DE 69715130 T2 DE69715130 T2 DE 69715130T2 DE 69715130 T DE69715130 T DE 69715130T DE 69715130 T DE69715130 T DE 69715130T DE 69715130 T2 DE69715130 T2 DE 69715130T2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- substituted
- alkyl
- hydrogen
- component
- 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
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 title claims description 61
- 238000004519 manufacturing process Methods 0.000 title description 6
- 238000010348 incorporation Methods 0.000 title 1
- 239000000049 pigment Substances 0.000 claims description 123
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 63
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 44
- 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 claims description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 35
- 230000008569 process Effects 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 31
- 239000011541 reaction mixture Substances 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 125000006413 ring segment Chemical group 0.000 claims description 19
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 15
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 11
- 238000001556 precipitation Methods 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- FVLUGNOOEZYDNV-UHFFFAOYSA-N 2,5-bis(4-methylanilino)terephthalic acid Chemical compound C1=CC(C)=CC=C1NC(C(=C1)C(O)=O)=CC(C(O)=O)=C1NC1=CC=C(C)C=C1 FVLUGNOOEZYDNV-UHFFFAOYSA-N 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
- NDOIVBNLFLMVIT-UHFFFAOYSA-N 2,5-dianilino-3,6-dioxocyclohexa-1,4-diene-1,4-dicarboxylic acid Chemical compound O=C1C(C(O)=O)=C(NC=2C=CC=CC=2)C(=O)C(C(=O)O)=C1NC1=CC=CC=C1 NDOIVBNLFLMVIT-UHFFFAOYSA-N 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 230000003750 conditioning effect Effects 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 239000012024 dehydrating agents Substances 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- LVTSHUZPPLHMEB-UHFFFAOYSA-N 2,5-bis(4-chloroanilino)terephthalic acid Chemical compound OC(=O)C=1C=C(NC=2C=CC(Cl)=CC=2)C(C(=O)O)=CC=1NC1=CC=C(Cl)C=C1 LVTSHUZPPLHMEB-UHFFFAOYSA-N 0.000 claims description 2
- UHNQJYAKDVEVGU-UHFFFAOYSA-N 2,5-bis(4-methoxyanilino)terephthalic acid Chemical compound C1=CC(OC)=CC=C1NC(C(=C1)C(O)=O)=CC(C(O)=O)=C1NC1=CC=C(OC)C=C1 UHNQJYAKDVEVGU-UHFFFAOYSA-N 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- 239000007787 solid Substances 0.000 description 37
- 239000002002 slurry Substances 0.000 description 22
- -1 amine salts Chemical class 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000003973 paint Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 17
- 238000006798 ring closing metathesis reaction Methods 0.000 description 17
- 239000002245 particle Substances 0.000 description 16
- 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 description 15
- 238000001914 filtration Methods 0.000 description 14
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 12
- 239000011230 binding agent Substances 0.000 description 12
- 239000000654 additive Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 239000006185 dispersion Substances 0.000 description 11
- 230000001965 increasing effect Effects 0.000 description 11
- 238000007363 ring formation reaction Methods 0.000 description 11
- 239000002966 varnish Substances 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 229920000180 alkyd Polymers 0.000 description 9
- 235000011007 phosphoric acid Nutrition 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 229940124530 sulfonamide Drugs 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000004800 polyvinyl chloride Substances 0.000 description 7
- 229920000915 polyvinyl chloride Polymers 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 229920000877 Melamine resin Polymers 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 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 6
- 239000007858 starting material Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- XRWXXHKKLFMVDD-UHFFFAOYSA-N 2,5-bis(n-sulfamoylanilino)terephthalic acid Chemical compound C=1C(C(O)=O)=C(N(C=2C=CC=CC=2)S(N)(=O)=O)C=C(C(O)=O)C=1N(S(=O)(=O)N)C1=CC=CC=C1 XRWXXHKKLFMVDD-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000000227 grinding Methods 0.000 description 5
- 238000003801 milling Methods 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000012552 review Methods 0.000 description 5
- 150000003456 sulfonamides Chemical class 0.000 description 5
- WIWJFWANKMRGGS-UHFFFAOYSA-N 3,4-dimethyl-1,6-dioxecane-2,5,7,10-tetrone Chemical compound C1(CCC(=O)OC(C(C(C(=O)O1)C)C)=O)=O WIWJFWANKMRGGS-UHFFFAOYSA-N 0.000 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 description 4
- 239000004925 Acrylic resin Substances 0.000 description 4
- 229920000178 Acrylic resin Polymers 0.000 description 4
- 229920003275 CYMEL® 325 Polymers 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- JMHCCAYJTTWMCX-QWPJCUCISA-M sodium;(2s)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate;pentahydrate Chemical compound O.O.O.O.O.[Na+].IC1=CC(C[C@H](N)C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 JMHCCAYJTTWMCX-QWPJCUCISA-M 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- 150000003460 sulfonic acids Chemical class 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- RBEJBFBZZAWKTP-UHFFFAOYSA-N 2,5-bis[4-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]anilino]terephthalic acid Chemical compound CC1=NOC(NS(=O)(=O)C=2C=CC(NC=3C(=CC(NC=4C=CC(=CC=4)S(=O)(=O)NC4=C(C(C)=NO4)C)=C(C(O)=O)C=3)C(O)=O)=CC=2)=C1C RBEJBFBZZAWKTP-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229920003265 Resimene® Polymers 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 230000001143 conditioned effect Effects 0.000 description 3
- 210000003298 dental enamel Anatomy 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000012860 organic pigment Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000006104 solid solution Substances 0.000 description 3
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 2
- BNSUAPUXTQJZDU-UHFFFAOYSA-N 2,5-bis[4-(diethylsulfamoyl)anilino]terephthalic acid Chemical compound C1=CC(S(=O)(=O)N(CC)CC)=CC=C1NC(C(=C1)C(O)=O)=CC(C(O)=O)=C1NC1=CC=C(S(=O)(=O)N(CC)CC)C=C1 BNSUAPUXTQJZDU-UHFFFAOYSA-N 0.000 description 2
- VKPQLZPZPYQFOK-UHFFFAOYSA-N 2-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=CC=C1S(Cl)(=O)=O VKPQLZPZPYQFOK-UHFFFAOYSA-N 0.000 description 2
- AVBIDYMRZQDJGP-UHFFFAOYSA-N 4-amino-n-(3-methoxypropyl)benzenesulfonamide Chemical compound COCCCNS(=O)(=O)C1=CC=C(N)C=C1 AVBIDYMRZQDJGP-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000004640 Melamine resin Substances 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 238000007580 dry-mixing Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000003966 growth inhibitor Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 2
- 150000003503 terephthalic acid derivatives Chemical class 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- GQJBHYJDDVVMED-UHFFFAOYSA-N 2,5-bis(4-sulfamoylanilino)terephthalic acid Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC(C(=C1)C(O)=O)=CC(C(O)=O)=C1NC1=CC=C(S(N)(=O)=O)C=C1 GQJBHYJDDVVMED-UHFFFAOYSA-N 0.000 description 1
- SJIQTGOBEGYKSI-UHFFFAOYSA-N 2-[(1,3-dioxoisoindol-2-yl)methyl]-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC1=CC=C(NC=2C(=CC3=C(C(C4=CC=CC=C4N3)=O)C=2)C2=O)C2=C1 SJIQTGOBEGYKSI-UHFFFAOYSA-N 0.000 description 1
- 229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
- LTFVELCIFWEGGA-UHFFFAOYSA-N 4-amino-n,n-diethylbenzenesulfonamide Chemical compound CCN(CC)S(=O)(=O)C1=CC=C(N)C=C1 LTFVELCIFWEGGA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
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- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
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- 235000011187 glycerol Nutrition 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
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- 125000000842 isoxazolyl group Chemical group 0.000 description 1
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- OBQVOBQZMOXRAL-UHFFFAOYSA-L magnesium;docosanoate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCCCCCC([O-])=O OBQVOBQZMOXRAL-UHFFFAOYSA-L 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
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- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical group C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
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- 239000004014 plasticizer Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
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- 239000003755 preservative agent Substances 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000004076 pyridyl group Chemical group 0.000 description 1
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- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
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- 229910052705 radium Inorganic materials 0.000 description 1
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- 229910052701 rubidium Inorganic materials 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
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- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000005028 tinplate Substances 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/748,742 US5755873A (en) | 1996-11-18 | 1996-11-18 | Incorporation of quinacridone additives during quinacridone preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69715130D1 DE69715130D1 (de) | 2002-10-10 |
| DE69715130T2 true DE69715130T2 (de) | 2003-01-16 |
Family
ID=25010732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69715130T Expired - Fee Related DE69715130T2 (de) | 1996-11-18 | 1997-11-06 | Einarbeitung von Chinacridonderivaten während des Chinacridonherstellungsverfahrens |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US5755873A (enExample) |
| EP (1) | EP0842987B1 (enExample) |
| JP (1) | JP4205190B2 (enExample) |
| CA (1) | CA2219294C (enExample) |
| DE (1) | DE69715130T2 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5972099A (en) * | 1997-12-17 | 1999-10-26 | Bayer Corporation | Process for preparing organic pigment compositions |
| US5868828A (en) * | 1998-05-20 | 1999-02-09 | Bayer Corporation | Heterocyclic-substituted quinacridone pigments |
| 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 |
| US6284890B1 (en) * | 1999-02-26 | 2001-09-04 | Ciba Specialty Chemicals Corp. | Aqueous process for the preparation of linear quinacridones having a reduced particle size |
| US6494948B2 (en) | 2000-12-22 | 2002-12-17 | Bayer Corporation | Preparation of quinacridone pigment compositions |
| 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 |
| JP2003096324A (ja) * | 2001-09-27 | 2003-04-03 | Dainippon Ink & Chem Inc | キナクリドンスルホン酸誘導体の製造方法 |
| WO2004067642A1 (en) * | 2003-01-28 | 2004-08-12 | Ciba Specialty Chemicals Holding Inc. | Synthesis of small particle size quinacridone of beta crystal phase |
| US7160380B2 (en) | 2003-09-22 | 2007-01-09 | Fuji Photo Film Co., Ltd. | Organic pigment fine-particle, and method of producing the same |
| JP5641929B2 (ja) * | 2007-04-24 | 2014-12-17 | サン・ケミカル・コーポレーション | 非水溶性インク及び塗料用の顔料 |
| JP7112578B1 (ja) * | 2021-10-05 | 2022-08-03 | 大日精化工業株式会社 | キナクリドン固溶体顔料の製造方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3157659A (en) * | 1959-10-10 | 1964-11-17 | Basf Ag | Process for preparing 2, 9-dichloro-quinacridone |
| DE1261106B (de) * | 1961-06-13 | 1968-02-15 | Hoechst Ag | Verfahren zur Verbesserung der Pigmenteigenschaften substituierter linearer Chinacridone |
| US3257405A (en) * | 1961-10-02 | 1966-06-21 | Allied Chem | Preparation of quinacridone pigments |
| US3386843A (en) * | 1963-10-01 | 1968-06-04 | Du Pont | Quinacridone pigments |
| US3317539A (en) * | 1965-08-20 | 1967-05-02 | Du Pont | Beta phase of 2, 9-dimethoxyquinacridone |
| DE2842468A1 (de) * | 1978-09-29 | 1980-04-10 | Hoechst Ag | Chinacridon-pigmentgemische, verfahren zu ihrer herstellung und ihre verwendung |
| JPS56118462A (en) * | 1980-02-25 | 1981-09-17 | Toyo Ink Mfg Co Ltd | Pigment composition |
| US4455173A (en) * | 1981-07-07 | 1984-06-19 | E. I. Du Pont De Nemours And Company | Preparation of pigmentary form of quinacridone pigments |
| DE3833423A1 (de) * | 1988-10-01 | 1990-04-19 | Hoechst Ag | Chinacridon-pigmente, verfahren zu ihrer herstellung und ihre verwendung |
| US5084100A (en) * | 1990-12-20 | 1992-01-28 | Ciba-Geigy Corporation | Quinacridone dispersion milling process |
| DE4325247A1 (de) * | 1993-07-28 | 1995-02-02 | Basf Ag | Pigmentzubereitungen mit Perylenderivaten als Dispergiermitteln |
| US5457203A (en) * | 1993-09-15 | 1995-10-10 | Ciba-Geigy Corporation | Pigmentary synthesis of quinacridone solid solutions |
| DE4403231A1 (de) * | 1994-02-03 | 1995-08-10 | Hoechst Ag | Verfahren zur Herstellung von Chinacridonpigmenten |
-
1996
- 1996-11-18 US US08/748,742 patent/US5755873A/en not_active Expired - Lifetime
-
1997
- 1997-10-24 CA CA002219294A patent/CA2219294C/en not_active Expired - Fee Related
- 1997-11-06 EP EP97119395A patent/EP0842987B1/en not_active Expired - Lifetime
- 1997-11-06 DE DE69715130T patent/DE69715130T2/de not_active Expired - Fee Related
- 1997-11-13 JP JP32720997A patent/JP4205190B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE69715130D1 (de) | 2002-10-10 |
| US5755873A (en) | 1998-05-26 |
| MX9708779A (es) | 1998-05-31 |
| EP0842987B1 (en) | 2002-09-04 |
| JP4205190B2 (ja) | 2009-01-07 |
| EP0842987A3 (en) | 1998-08-05 |
| EP0842987A2 (en) | 1998-05-20 |
| CA2219294C (en) | 2007-01-09 |
| CA2219294A1 (en) | 1998-05-18 |
| JPH10158536A (ja) | 1998-06-16 |
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| 8364 | No opposition during term of opposition | ||
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Owner name: SUN CHEMICAL CORP., FORT LEE, N.J., US |
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| 8327 | Change in the person/name/address of the patent owner |
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