CN1946811A - 高纯度萘酚as颜料 - Google Patents
高纯度萘酚as颜料 Download PDFInfo
- Publication number
- CN1946811A CN1946811A CNA2005800124906A CN200580012490A CN1946811A CN 1946811 A CN1946811 A CN 1946811A CN A2005800124906 A CNA2005800124906 A CN A2005800124906A CN 200580012490 A CN200580012490 A CN 200580012490A CN 1946811 A CN1946811 A CN 1946811A
- Authority
- CN
- China
- Prior art keywords
- pigment
- naphthol
- pigments
- phenyl
- hydrogen
- 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.)
- Pending
Links
- 239000000049 pigment Substances 0.000 title claims abstract description 91
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 title description 6
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000000976 ink Substances 0.000 claims description 38
- -1 phenyl amino formyl Chemical group 0.000 claims description 26
- 239000004615 ingredient Substances 0.000 claims description 22
- 239000000725 suspension Substances 0.000 claims description 21
- 239000000463 material Substances 0.000 claims description 20
- 238000007639 printing Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 229920005989 resin Polymers 0.000 claims description 11
- 239000011347 resin Substances 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 239000000460 chlorine Chemical group 0.000 claims description 8
- 229910052801 chlorine Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 7
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 6
- 238000006149 azo coupling reaction Methods 0.000 claims description 6
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000011368 organic material Substances 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 2
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 239000010408 film Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- 239000003795 chemical substances by application Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000001514 detection method Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 150000004780 naphthols Chemical class 0.000 description 10
- AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000012530 fluid Substances 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- 239000001993 wax Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 150000001989 diazonium salts Chemical class 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000012752 auxiliary agent Substances 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- NQPMHBRLFWMCTR-UHFFFAOYSA-N n-(chloromethoxy)aniline Chemical compound ClCONC1=CC=CC=C1 NQPMHBRLFWMCTR-UHFFFAOYSA-N 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000004530 micro-emulsion Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000003791 organic solvent mixture Substances 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229920001807 Urea-formaldehyde Polymers 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012943 hotmelt Substances 0.000 description 3
- 239000004816 latex Substances 0.000 description 3
- 229920000126 latex Polymers 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000011144 upstream manufacturing Methods 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 239000008351 acetate buffer Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 2
- 235000021240 caseins Nutrition 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000005352 clarification Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000013530 defoamer Substances 0.000 description 2
- 238000011026 diafiltration Methods 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 229920003987 resole Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- CFQPVBJOKYSPKG-UHFFFAOYSA-N 1,3-dimethylimidazol-2-one Chemical compound CN1C=CN(C)C1=O CFQPVBJOKYSPKG-UHFFFAOYSA-N 0.000 description 1
- KPAPHODVWOVUJL-UHFFFAOYSA-N 1-benzofuran;1h-indene Chemical compound C1=CC=C2CC=CC2=C1.C1=CC=C2OC=CC2=C1 KPAPHODVWOVUJL-UHFFFAOYSA-N 0.000 description 1
- ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical compound COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 description 1
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- UHOPWFKONJYLCF-UHFFFAOYSA-N 2-(2-sulfanylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)C2=C1 UHOPWFKONJYLCF-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- WFRBDWRZVBPBDO-UHFFFAOYSA-N 2-methyl-2-pentanol Chemical compound CCCC(C)(C)O WFRBDWRZVBPBDO-UHFFFAOYSA-N 0.000 description 1
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical class CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
- KRIMXCDMVRMCTC-UHFFFAOYSA-N 2-methylhexan-2-ol Chemical compound CCCCC(C)(C)O KRIMXCDMVRMCTC-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 239000013032 Hydrocarbon resin Substances 0.000 description 1
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- GLLRIXZGBQOFLM-UHFFFAOYSA-N Xanthorin Natural products C1=C(C)C=C2C(=O)C3=C(O)C(OC)=CC(O)=C3C(=O)C2=C1O GLLRIXZGBQOFLM-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000000227 bioadhesive Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- NQIZDFMZAXUZCZ-UHFFFAOYSA-N carbifene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCC)C(=O)N(C)CCN(C)CCC1=CC=CC=C1 NQIZDFMZAXUZCZ-UHFFFAOYSA-N 0.000 description 1
- 229950003365 carbifene Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 210000004534 cecum Anatomy 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920001727 cellulose butyrate Polymers 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229920006270 hydrocarbon resin Polymers 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 238000010309 melting process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000001471 micro-filtration Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- ORSCIKBWIBQCTR-UHFFFAOYSA-N n,n-dimethylacetamide;urea Chemical class NC(N)=O.CN(C)C(C)=O ORSCIKBWIBQCTR-UHFFFAOYSA-N 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000012465 retentate Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000002700 tablet coating Substances 0.000 description 1
- 238000009492 tablet coating Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000002525 ultrasonication Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000002348 vinylic group Chemical group 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 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
- C09B41/00—Special methods of performing the coupling reaction
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0093—Microreactors, e.g. miniaturised or microfabricated reactors
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
- C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series
-
- 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
- C09B41/00—Special methods of performing the coupling reaction
- C09B41/006—Special methods of performing the coupling reaction characterised by process features
-
- 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0079—Azoic dyestuff preparations
-
- 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
- C09B67/0096—Purification; Precipitation; Filtration
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00781—Aspects relating to microreactors
- B01J2219/00783—Laminate assemblies, i.e. the reactor comprising a stack of plates
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00781—Aspects relating to microreactors
- B01J2219/00873—Heat exchange
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Paints Or Removers (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
本发明涉及式(Ⅵ)的萘酚AS颜料,其具有由右述上限限定的最大含量的副组分(1)-(5)(参见表)。
Description
技术领域
本发明涉及偶氮颜料的领域。
背景技术
萘酚AS颜料是工业界特别感兴趣的,这是由于它们通常达到高着色强度和覆盖工艺油墨组配的品红色区域。它们也具有良好的耐晒牢度。
萘酚AS颜料传统上采用间歇方法生产。这些方法的共同特征是要求工艺参数的精确控制和维持:例如温度、时间、充分混合和着色剂浓度以及悬浮液浓度对于收率、色彩性能和获得的颜料的坚牢度以及对于它们的品质恒定性是决定性的。相似地,例如由于罐和搅拌器几何结构或热传递对初级粒子尺寸、粒度分布和色彩性能具有显著影响,所以新产品从实验室规模到大工业规模的放大对于间歇工艺是昂贵和费力的,和可能带来困难。尽管在合成时的所有工艺最优化,但常规生产的偶氮颜料由工艺决定有时还包含残余数量的未转化的起始材料以及由副反应形成的副产物。特别对于用于无接触印刷工艺,如小型办公室/家庭办公室打印机的那些颜料,高化学纯度是绝对必要的。对于某些应用,例如日用消费品的着色,对于使用的着色剂存在对于伯芳族胺、萘酚和三氮烯的特定极限值。
发明内容
本发明的目的是提供包含明显降低含量的不希望的副组分的萘酚AS颜料。
本发明因此提供式(IV)的萘酚AS颜料
其中
X1是氢、卤素、硝基、氨基甲酰基、苯基氨基甲酰基、氨磺酰基、苯基氨磺酰基、C1-C4烷基氨磺酰基或二(C1-C4)烷基氨磺酰基;
X2是氢或卤素;
Y是氢、卤素、硝基、C1-C4烷基、C1-C4烷氧基或C1-C4烷氧基羰基;和
Z是苯基、萘基、苯并咪唑酮基、苯基或由卤素、硝基、C1-C4烷基和/或C1-C4烷氧基取代的苯基,
具有由下述上限限定的最大含量的下文所述的副组分(1)-(5):
其中Ar具有含义
每种情况下由高压液相色谱(HPLC)测定。
对于本发明的目的优选是式(IV)的萘酚AS颜料,该颜料的副组分1的含量最高为80ppm和特别是最高为60ppm。
对于本发明的目的优选是式(IV)的萘酚AS颜料,该颜料的副组分2的含量小于50ppm的检测极限。
对于本发明的目的优选是式(IV)的萘酚AS颜料,该颜料的副组分3的含量小于50ppm的检测极限。
对于本发明的目的优选是式(IV)的萘酚AS颜料,该颜料的副组分4的含量小于50ppm的检测极限。
对于本发明的目的优选是式(IV)的萘酚AS颜料,该颜料的副组分5的含量最高为200ppm和特别是最高为100ppm。
副组分(1)-(5)可以按如下路径形成:
(1):由使用的重氮化合物的离解形成;
(2):由使用的偶合剂的酰胺键的离解形成;
(3):从如上所述释放的重氮化合物和胺(1)形成;
(4):从如上所述释放的重氮化合物和胺(2)形成;
(5):是未转化的偶合剂。
为由HPLC测定副组分,将式(IV)的化合物的样品(每个样品0.5g)干燥,由此采用N-甲基吡咯烷酮和甲醇制备悬浮液和通过装配有UV-Vis检测器的HPLC系统分析滤液。
对于本发明的目的优选是式(IV)的高纯度萘酚AS颜料,其中
Y是氢、甲氧基、甲氧基羰基、甲基或氯;
X1在5位且是氢、氯、硝基、氨基甲酰基、苯基氨基甲酰基、氨磺酰基、苯基氨磺酰基、甲基氨磺酰基或二甲基氨磺酰基;
X2在4位且是氢或氯;和
Z是由氯、硝基、C1-C2烷基和/或C1-C2-烷氧基取代的苯基。
对于本发明的目的特别优选是颜料C.I.颜料红146、147、176、184、185、269。
本发明也提供生产这样高纯度萘酚AS颜料的方法,该方法的特征是
(a)在微型反应器中至少进行偶氮偶合,
(b)在0-60℃的温度下将微型反应器中生产的萘酚AS颜料与选自C3-C6醇、C4-C10醚醇和卤代芳族化合物的有机溶剂充分接触,和/或
(c)在含水或含溶剂的悬浮液中将微型反应器中生产的萘酚AS颜料进行膜纯化。
步骤(c)也可以在步骤(b)之前进行。在一些情况下也可能已经通过步骤(b)或(c)之一达到所需的纯度。
(a)微型反应器中的合成:
可用的微型反应器包括在WO01/59013A1中描述的设备。微型反应器从多个小板构造,该多个小板在彼此上方堆叠和彼此连接,且其表面带有微机械方式产生的结构,该结构相互作用形成用于实施化学反应的反应空间。存在至少一个贯穿该系统的连接到入口和出口的通道。材料物流的流量由设备限制,例如由依赖于微型反应器的几何结构设计出现的压力限制。期望微型反应器中的反应完全进行,但也可以接着存在停留区以提供可能要求的停留时间。流量有利地为0.05-5l/min,优选0.05-500ml/min,更优选0.05-250ml/min和特别地0.1-100ml/min。
微反应系统连续操作,在此每种情况下彼此混合的流体数量在微升(μl)到毫升(ml)范围内变动。反应器内部微结构化区域的尺寸对于此微反应系统中萘酚AS颜料的生产是决定性的。这些尺寸必须选择这样大,使得特别地固体粒子可通过而没有问题和故不堵塞通道。微结构的最小净宽应当比最大颜料粒子的直径大出约十倍。此外,必须通过适当的几何设计保证没有死水区,例如盲端或尖角,其中颜料粒子例如可沉降。因此优选是具有圆角的连续路径。结构必须足够小以利用微反应技术的固有优点,即优异的热控制,层流,扩散混合和低内部反应体积。
输送溶液或悬浮液的通道的净宽有利地是5-10000μm,优选5-2000μm,更优选10-800μm,特别地20-700μm。
换热器通道的净宽主要依赖于输送流体或悬浮液的通道的净宽和有利地小于或等于10000μm,优选小于或等于2000μm和特别是小于或等于800μm。换热器通道的净宽的下限不是关键的和至多由要泵送的换热器流体的压力增量和由最优化的供热或散热的必要性限制。使用的微反应系统的尺寸是:
换热器结构: 通道宽度约600μm,通道高度:约250μm;
混合器和停留时间:通道宽度约600μm,通道高度:约500μm。
优选从上方向微型反应器中加入所有的换热器流体和反应物。同样优选向上方输出产物和换热器流体。通过紧邻位于反应器上游的T形支路实现参与反应的第三种和第四种流体(例子是缓冲溶液)的可能供应,即反应物各自可以与缓冲溶液预先混合。优选通过精确活塞泵和计算机控制的调控系统控制必要的浓度和流量。通过集成传感器监测反应温度并借助于调控系统和恒温器/低温恒温器监测和控制反应温度。使用材料的混合物的制备也可以预先在微混合器中或在上游混合区中进行。也可以将使用材料计量入下游混合区或计量入下游微混合器或反应器。在此使用的系统由不锈钢制成;其它材料,例如玻璃、陶瓷、硅、塑料或其它金属同样可使用。
除偶氮偶合外,重氮化也可以在微型反应器中进行。也可以在串联的微型反应器中进行这两个阶段。
有利地将反应物作为水溶液或悬浮液和优选以化学计量量/当量数量输送到微型反应器。偶氮偶合反应优选在水溶液或悬浮液中进行,但也可以单独或作为与水的混合物形式使用有机溶剂,例如,含有1-10个碳原子的醇,例子是甲醇、乙醇、正丙醇、异丙醇,丁醇,如正丁醇、仲丁醇、叔丁醇,戊醇,如正戊醇和2-甲基-2-丁醇,己醇,如2-甲基-2-戊醇、3-甲基-3-戊醇、2-甲基-2-己醇和3-乙基-3-戊醇,辛醇,如2,4,4-三甲基-2-戊醇,和环己醇;或二醇,如乙二醇、二甘醇、丙二醇、二丙二醇,或甘油;聚二醇,如聚乙二醇或聚丙二醇;醚,如甲基异丁基醚、四氢呋喃或二甲氧基乙烷;二醇醚,如乙二醇或丙二醇的单甲基醚或单乙基醚、二甘醇单甲基醚、二甘醇单乙基醚、丁基乙二醇或甲氧基丁醇;酮,如丙酮、二乙基酮、甲基异丁基酮、甲乙酮或环己酮;脂族酰胺,如甲酰胺、二甲基甲酰胺、N-甲基乙酰胺或N,N-二甲基乙酰胺;脲衍生物,如四甲基脲;或环状羧酰胺,如N-甲基吡咯烷酮、戊内酰胺或己内酰胺;酯,如羧酸-C1-C6烷基酯,如甲酸丁酯、乙酸乙酯或丙酸丙酯;或羧酸-C1-C6二醇酯;或二醇醚乙酸酯,如乙酸-1-甲氧基-2-丙基酯;或邻苯二甲酸-或苯甲酸-C1-C6烷基酯,如苯甲酸乙酯;环状酯,如己内酯;腈,如乙腈或苄腈;脂族或芳族烃,如环己烷或苯;或由烷基、烷氧基、硝基或卤素取代的苯,如甲苯、二甲苯、乙苯、苯甲醚、硝基苯、氯苯、邻二氯苯、1,2,4-三氯苯或溴苯;或其它取代的芳族化合物,如苯甲酸或苯酚;芳族杂环,如吡啶、吗啉、甲基吡啶或喹啉;以及六甲基磷酰三胺、1,3-二甲基-2-咪唑啉酮、二甲亚砜和环丁砜。所述溶剂也可以作为混合物形式使用。优选使用可与水混溶的溶剂。
本发明的方法中也可采用常规方法中使用的助剂,例如表面活性剂,颜料性和非颜料性分散剂,填料,标准化剂,树脂,蜡,消泡剂,防尘剂,增量剂,配色着色剂,防腐剂,干燥延迟剂,流变控制添加剂,湿润剂,抗氧化剂,UV吸收剂,光稳定剂或其组合。可以在微反应器中的反应之前、期间或之后的任何时间点,一次性或分多份加入助剂。例如,助剂可以直接加入反应物的溶液或悬浮液中,也可在反应期间采用流体、被溶解或被悬浮的形式加入。加入的助剂的总数量可为0-40wt%,优选1-30wt%,更优选2.5-25wt%,基于萘酚AS颜料。
合适的表面活性剂包括阴离子或阴离子活性的、阳离子或阳离子活性的和非离子型的物质或这些试剂的混合物。可用于本发明的方法的表面活性剂、颜料性和非颜料性分散剂的例子在EP-A-1195411中有说明。
由于在反应期间和之后对所需pH值的保持对于品质经常是决定性的,所以也可以输入缓冲溶液,优选有机酸及其盐的缓冲溶液,例如甲酸/甲酸盐缓冲剂、乙酸/乙酸盐缓冲剂、柠檬酸/柠檬酸盐缓冲剂;或无机酸及其盐的缓冲溶液,如磷酸/磷酸盐缓冲剂或碳酸/碳酸氢盐或碳酸盐缓冲剂。
(b)溶剂洗涤:
本发明的溶剂洗涤包括直接来自微型反应器或在中间分离之后例如作为滤饼(固体含量约5wt%-30wt%)形式的步骤(a)中制备的萘酚AS颜料在提及的有机溶剂之一中的吸收。优选的溶剂在此是C3-C4醇、二醇醚和氯代苯,例如丁氧基乙醇、邻二氯苯、异丁醇、异丙醇或其混合物。也可以使用按照(c)处理的颜料悬浮液。
溶剂的数量优选为1体积%-30体积%和特别地5体积%-15体积%,基于颜料悬浮液的体积,或1-10倍重量的溶剂,基于滤饼中颜料的重量。将颜料悬浮液或滤饼和溶剂的混合物优选在10℃-50℃和特别地20℃-45℃的温度下搅拌优选0.1-2小时和特别地0.25-1小时,且优选在常压下搅拌。可以使用常用的搅拌设备,例如实验室搅拌器用于搅拌。然而,原则上也可以在接收容器的循环泵送系统中使用装配适当分散工具的在线分散机。这样的分散机不仅仅保证悬浮液在接收容器中的深度充分混合,而且具有解附聚作用,使得暴露任何夹杂物。将溶剂处理的颜料悬浮液随后过滤和洗涤或输送到膜纯化(c)。
(c)膜纯化:
本发明的膜纯化阶段包括将从步骤(a)或从(b)获得的偶氮着色剂悬浮液这样导引通过膜装置,该膜装置具有这样的性质,使得萘酚AS颜料由膜尽可能完全地保留。液体介质可以特别地是水或有机溶剂,如果适当地,采用与水的混合物。悬浮液中的固体浓度有利地为1wt%-10wt%和优选2wt%-5wt%,基于悬浮液的总重量。透膜的物质输运的驱动力是在膜两侧之间的压差。压差有利地为0.5-5巴和优选1-2巴。压力例如由合适的泵产生,例子是活塞泵。使用的膜例如是典型分离极限是100-106g/mol的陶瓷或聚合物膜。优选使用静态膜组件,如管状或板状组件,或动态膜组件。温度有利地为0-100℃和特别地20-80℃。
膜纯化也可以作为膜渗滤形式进行。在此情况下,将保留物,即偶氮颜料再循环输送回初始容器和由补充供给保持水或溶剂含量恒定。与传统优化的间歇操作相比,本发明的方法可实现如下产品改进:
步骤(a)显著降低三氮烯和混合三氮烯的含量,即多数情况下降低到低于50ppm的检测极限,但通常总是仍有高于100ppm的游离芳族胺H2N-Ar和未转化偶合组分,即萘酚存在。
通过步骤(b)或步骤(c),优选步骤(b)与步骤(c)的结合令人惊奇地成功降低游离胺和萘酚含量经常直到低于25ppm或100ppm的各自检测极限。作为膜纯化的副作用,无机盐也被保留。
根据本发明的高纯度萘酚AS颜料特别用于将如下物质着色:电子照相调色剂和显影剂,例如单组分或双组分粉末调色剂(也称为单组分或双组分显影剂)、磁性调色剂、液体调色剂、胶乳调色剂、聚合调色剂以及特种调色剂,粉末涂料、喷墨油墨和滤色器,以及作为电子油墨(“e-油墨”)或电子纸(“e-纸”)的着色剂。调色剂粒子也可用于化妆品和药物应用,如用于片剂包衣。
典型的调色剂粘结剂是加成聚合、聚加成和缩聚树脂,如苯乙烯、苯乙烯-丙烯酸酯、苯乙烯-丁二烯、丙烯酸酯、聚酯、酚醛-环氧树脂、聚砜、聚氨酯,单独或组合使用,以及聚乙烯和聚丙烯,它们可还包含另外的成分,如电荷控制剂、蜡或流动助剂,或后续由这些添加剂改性。
本发明的萘酚AS颜料显然地也可非常普遍地用于将天然或合成来源的高分子量有机材料着色,例如将塑料、树脂、涂料、油漆、电子照相调色剂和显影剂、驻极体材料、滤色器着色,以及将包括印刷油墨在内的油墨,和种子着色。
可以由本发明的萘酚AS颜料着色的高分子量有机材料例如是纤维素化合物,如纤维素醚和纤维素酯,如乙基纤维素、硝化纤维素、乙酸纤维素或丁酸纤维素,天然粘结剂,例如脂肪酸、脂肪油、树脂和它们的转化产物,或人造树脂,如缩聚物、聚加合物、加成聚合物和加成共聚物,例如氨基塑料,特别地脲-和蜜胺-甲醛树脂、醇酸树脂、丙烯酸类树脂、酚醛塑料和酚醛树脂,如线性酚醛清漆或甲阶酚醛树脂,脲树脂,乙烯基类聚合物如聚乙烯醇、聚乙烯醇缩醛、聚乙酸乙烯酯或聚乙烯基醚,聚碳酸酯,聚烯烃,如聚苯乙烯、聚氯乙烯、聚乙烯或聚丙烯,聚(甲基)丙烯酸酯和它们的共聚物,如聚丙烯酸酯或聚丙烯腈、聚酰胺、聚酯、聚氨酯、苯并呋喃-茚树脂和烃树脂、环氧树脂、具有不同固化机理的不饱和人造树脂(聚酯,丙烯酸酯)、蜡、醛树脂和酮树脂、树胶、橡胶和其衍生物和胶乳、酪蛋白、硅酮和有机硅树脂,它们单独或混合使用。提及的高分子量有机化合物是否作为塑性的物料、熔体或以纺丝溶液、分散体、清漆、油漆或印刷油墨的形式存在不是重要的。依赖于预计的用途,经证实有利的是作为共混物形式或以制剂或分散体的形式使用本发明的萘酚AS颜料。基于要着色的高分子量有机材料,本发明的萘酚AS颜料的使用数量为0.05wt%-30wt%和优选0.1wt%-15wt%。
对于其虽然不需要高纯度颜料但必须满足某些纯度标准的应用,从经济上考虑可能有意义的是共混本发明的萘酚AS颜料与常规生产的萘酚AS颜料,使得仍然满足要求的纯度。在一些情况下也可以使用BET表面积大于2m2/g和优选大于5m2/g的对应粗产品代替经研磨和/或整理的本发明萘酚AS颜料。此粗产品可以单独或如果适当地则与其它粗产品或成品颜料混合地,用于生产液体或固体形式的5wt%-99wt%浓度的色母料。
本发明进一步提供所述的着色剂制剂作为可喷射印刷油墨(Drucktinten),特别地喷墨油墨的着色剂的用途。喷墨油墨不仅仅表示含水基(包括微乳液油墨)和非含水基(溶剂基)的油墨,可UV固化的油墨,而且表示由热熔工艺操作的油墨。溶剂基喷墨油墨基本上包含0.5-30wt%和优选1wt%-15wt%一种或多种本发明的萘酚AS颜料,70wt%-95wt%有机溶剂或溶剂混合物和/或助水溶化合物。如果适当地,溶剂基喷墨油墨可包含可溶于溶剂中的载体材料和粘结剂,例子是聚烯烃、天然橡胶、合成橡胶、聚氯乙烯、氯乙烯-乙酸乙烯酯共聚物、聚乙烯醇缩丁醛、蜡-胶乳体系或这些化合物的组合。如果适当地,溶剂基喷墨油墨可包含进一步的添加剂,例子是湿润剂,脱气剂/消泡剂,防腐剂和抗氧化剂。微乳液油墨基于有机溶剂、水和如果适当地还有用作界面介质的另外物质(表面活性剂)。微乳液油墨包含0.5-30wt%和优选1wt%-15wt%本发明的萘酚AS颜料,0.5wt%-95wt%水和0.5wt%-95wt%有机溶剂和/或界面介质。可UV固化的油墨基本上包含0.5-30wt%一种或多种本发明的萘酚AS颜料,0.5wt%-95wt%水,0.5wt%-95wt%有机溶剂或溶剂混合物,0.5wt%-50wt%可辐射固化的粘结剂和如果适当地,0wt%-10wt%光敏引发剂。热熔油墨通常基于在室温下为固体和在加热时液化的蜡、脂肪酸、脂肪醇或磺酰胺,在此优选的熔融范围是约60-约140℃。热熔喷墨油墨基本上由20wt%-90wt%蜡和1wt%-10wt%一种或多种本发明的萘酚AS颜料组成。它们可进一步包含0wt%-20wt%另外的聚合物(作为“染料溶解剂”),0wt%-5wt%分散剂,0wt%-20wt%粘度改进剂,0wt%-20wt%增塑剂,0wt%-10wt%粘性添加剂,0wt%-10wt%透明度稳定剂(例如防止蜡的结晶)以及0wt%-2wt%抗氧化剂。
可以通过将萘酚AS颜料分散入微乳液介质中、分散入非含水介质中或分散入生产可UV固化的油墨的介质中或分散入生产热熔喷墨油墨的蜡中,而生产本发明的可喷射印刷油墨,特别地喷墨油墨。有利地,为喷墨应用将在此获得的可喷射印刷油墨随后过滤,例如通过1μm过滤器。
本发明的萘酚AS颜料进一步也适用作滤色器的着色剂(该滤色器不仅用于加法色生成而且用于减法色生成),以及作为电子油墨(“e-油墨”)或电子纸(“e-纸”)的着色剂。在生产所述滤色器(不仅指反射性滤色器而且指透光性滤色器)中,将颜料以糊剂的形式或作为在合适粘结剂(丙烯酸酯,丙烯酸类酯,聚酰亚胺,聚乙烯醇,环氧化物,聚酯,蜜胺,明胶,酪蛋白)中的着色光致抗蚀剂形式施加到各自的LCD构件(例如TFT-LCD=薄膜晶体管液晶显示器或例如((S)TN-LCD=(超)扭转向列型-LCD)。除了高热稳定性以外,高颜料纯度对于稳定糊剂或着色光致抗蚀剂也是先决条件。此外,着色的滤色器也可以由喷墨印刷工艺或其它合适的印刷工艺施加。
具体实施方式
实施例1:C.I.颜料红269
a1)制备茴香碱(Anisbase)重氮盐溶液:
加入2532g水作为初始进料并在室温下首先将242g的3-氨基-4-甲氧基-N-苯甲酰苯胺均匀搅拌入,由盐酸的加入进行沉淀和采用1.5kg冰/水冷却到10℃。在将沉淀的盐酸盐采用138ml亚硝酸钠溶液(40%)重氮化中最终形成可容易搅拌的茴香碱重氮溶液。此溶液在向其中加入澄清助剂后滤出到接收容器中。由氨基磺酸的加入脱除过量亚硝酸盐。
a2)制备用于茴香碱重氮盐溶液的缓冲剂:
加入1884g冰/水作为初始进料并加入502g乙酸以及加入614g氢氧化钠水溶液,和在加入1kg水之后保持温度在室温下。
a3)制备偶合组分(萘酚AS-CA)的溶液:
将包含湿润助剂的2720g水加入作为初始进料并加热到80℃。在搅拌的同时,将328g的N-(5-氯-2-甲氧基苯基)-3-羟基萘-2-羧酰胺引入和在碱性条件下溶解。通过加入另外的2720g冰/水,将萘酚AS溶液冷却到室温。最后在加入澄清助剂的条件下将其过滤。
a4)微型反应器中的偶氮偶合:
将茴香碱重氮盐溶液和萘酚AS溶液在8ml/min的流量下泵送入微型反应器(型号:CPC-Systems/法兰克福公司的Cytos)的各自反应物入口。为达到对于偶氮偶合必需的4.8-5.0的pH值,刚好在反应器入口上游将反应物溶液采用根据a2)制备的乙酸/乙酸盐缓冲剂稀释。在每种情况下在6ml/min的流量下同样借助于校准的活塞泵通过T形支路将缓冲溶液输送入微型反应器的反应物进料管线。将微型反应器的换热器回路连接到设定为20℃-35℃的所需反应温度的恒温器。将偶合的颜料悬浮液(21℃,pH=5.0)在接收容器中收集和进行如下溶剂洗涤。
b)溶剂洗涤:
将从微型反应器获得的颜料悬浮液与一定数量的丁氧基乙醇混合,使得整个淤浆包含约10体积%的丁氧基乙醇。将淤浆在约45℃的温度下搅拌30分钟,滤出和采用水洗涤。在取样之后,将着色剂-溶剂-水悬浮液进行如下膜纯化。
c)膜纯化:
使用对于分离选择性层的标称分离极限为60nm和膜面积为0.09m2的陶瓷多通道微过滤膜。将约15kg颜料含量为约2wt%的着色剂悬浮液加入温度可控制的接收容器中作为初始进料。将膜在保留物侧在环境温度下以约1.5巴的压力进汽冲击。为保证接收容器中的恒定体积,采用间歇方式由软化水替代分离除去的渗透物的质量。在这些条件下,完全保留颜料和将有机副组分降低到表2中所列的数值。交换体积(即输入的软化水体积/使用的颜料悬浮液体积)是约4。渗透物流量是约200l/(m2·h·巴)。
同时,在10小时渗滤后,初始的氯离子含量从2.5%降低至920ppm以及硫酸根含量从初始的0.3%降低至30ppm。
d)分析:
将取出的样品(每个0.5g)干燥,与每种情况下10ml的N-甲基吡咯烷酮混合和由超声粉碎15min。在加入20ml甲醇和再次研磨15min之后,滤出悬浮液。在每种情况下,将20μl滤液引入HPLC系统的自动取样器和由UV-Vis检测器在240和375nm下检测(分离柱Nucleosil120-5 C18(长度:25cm,i=4.6mm);对于1ml/min的总流量,流动相采用各种组成由缓冲剂(575mg的NH4H2PO4加上1000g的H2O加上3.0g的NaN3(pH5.0))和甲醇Chromasolv组成)。
表2列出在每个步骤之后的副组分的含量:
表2显示常规间歇法颜料的典型副组分含量与来自微型反应器中的合成[步骤(a)]和随后溶剂洗涤[步骤(b)]和膜纯化[步骤(c)]的颜料的副组分含量的比较。
为归类和评定表2中的数值,参考表1中列出的考虑的副组分的检测极限值。选择的分析方法的测量精度是约±5ppm。
表1:副组分的检测极限:
副组分 | 检测极限 |
茴香碱,如3-氨基-4-甲氧基-N-苯甲酰苯胺 | 25ppm |
氯甲氧基苯胺 | 50ppm |
茴香碱三氮烯 | 50ppm |
混合三氮烯 | 50ppm |
萘酚AS-CA | 100ppm |
表2:得自间歇合成,或微型反应器合成与随后溶剂洗涤和膜纯化结合的颜料中副组分含量的比较
间歇法颜料 | 在[步骤a)]之后的颜料 | 在溶剂洗涤[步骤b)]之后的颜料 | 在膜纯化[步骤c)]之后的颜料 | |
3-氨基-4-甲氧基-N-苯甲酰苯胺 | 132ppm | 100ppm | 80ppm | 60ppm |
氯甲氧基苯胺 | 54ppm | 50ppm | n.n.* | n.n.* |
茴香碱三氮烯 | 134ppm | n.n.* | n.n.* | n.n.* |
混合三氮烯 | 138ppm | n.n.* | n.n.* | n.n.* |
萘酚AS-CA | 500ppm | <100ppm | <100ppm | <100ppm |
*:不可检出,即小于表1的检测极限。
实施例2:C.I.颜料红146
相似于实施例1进行步骤a)-d)。在步骤c)之后获得的颜料含有低于各自检测极限的茴香碱、氯甲氧基苯胺、茴香碱三氮烯和萘酚AS。
实施例3:C.I.颜料红147
相似于实施例1进行步骤a)-d)。在步骤c)之后获得的颜料含有低于各自检测极限的茴香碱、氯甲氧基苯胺、茴香碱三氮烯和萘酚AS。
对比例2和3:
总共80次间歇批次的平均数值:
茴香碱 519ppm
氯甲氧基苯胺 32ppm
茴香碱三氮烯 446ppm
萘酚AS 1.10%
Claims (10)
2.权利要求1的颜料,其特征为副组分(1)的含量最高为80ppm。
3.权利要求1或2的颜料,其特征为副组分(1)的含量最高为60ppm。
4.权利要求1-3中一项或多项的颜料,其特征为副组分(5)的含量最高为200ppm。
5.权利要求1-4中一项或多项的颜料,其特征为副组分(5)的含量最高为100ppm。
6.权利要求1-5中一项或多项的颜料,其特征为
Y是氢、甲氧基、甲氧基羰基、甲基或氯;
X1在5位且是氢、氯、硝基、氨基甲酰基、苯基氨基甲酰基、氨磺酰基、苯基氨磺酰基、甲基氨磺酰基或二甲基氨磺酰基;
X2在4位且是氢或氯;和
Z是由氯、硝基、C1-C2烷基和/或C1-C2烷氧基取代的苯基。
7.权利要求1-6中一项或多项的颜料,其特征为该颜料是选自C.I.颜料红146、147、176、184、185和269的颜料。
8.生产根据权利要求1-7中一项或多项的萘酚AS颜料的方法,其特征为
(a)在微型反应器中至少进行偶氮偶合,
(b)在0-60℃的温度下将微型反应器中生产的萘酚AS颜料与选自C3-C6醇、C4-C10醚醇和卤代芳族化合物的有机溶剂充分接触,和/或
(c)在含水或含溶剂的悬浮液中将微型反应器中生产的萘酚AS颜料进行膜纯化。
9.根据权利要求1-7中一项或多项的萘酚AS颜料用于将如下物质着色的用途:天然或合成来源的高分子量有机材料,特别是塑料、树脂、涂料、油漆、电子照相调色剂和显影剂、驻极体材料、滤色器,以及包括印刷油墨在内的油墨,和种子。
10.权利要求9的用途,用于将单组分或双组分粉末调色剂、磁性调色剂、液体调色剂、聚合调色剂着色,将喷墨油墨着色,用作滤色器中的着色剂,以及用作电子油墨或电子纸的着色剂。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102004019560A DE102004019560A1 (de) | 2004-04-22 | 2004-04-22 | Hochreine Naphthol AS-Pigmente |
DE102004019560.9 | 2004-04-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1946811A true CN1946811A (zh) | 2007-04-11 |
Family
ID=34962425
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNA2005800124906A Pending CN1946811A (zh) | 2004-04-22 | 2005-04-06 | 高纯度萘酚as颜料 |
Country Status (9)
Country | Link |
---|---|
US (1) | US20070240618A1 (zh) |
EP (1) | EP1740658A1 (zh) |
JP (1) | JP2007533802A (zh) |
KR (1) | KR20060135896A (zh) |
CN (1) | CN1946811A (zh) |
BR (1) | BRPI0510073A (zh) |
CA (1) | CA2563812A1 (zh) |
DE (1) | DE102004019560A1 (zh) |
WO (1) | WO2005105928A1 (zh) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103424987A (zh) * | 2012-05-21 | 2013-12-04 | 东洋油墨Sc控股株式会社 | 滤色器用着色组合物以及滤色器 |
CN103421345A (zh) * | 2012-05-21 | 2013-12-04 | 东洋油墨Sc控股株式会社 | 颜料组合物、其制造方法、着色组合物以及滤色器 |
CN105524484A (zh) * | 2016-01-14 | 2016-04-27 | 上虞市新利化工有限公司 | 一种c.i.颜料红176的制备方法 |
CN106257332A (zh) * | 2015-06-19 | 2016-12-28 | 富士施乐株式会社 | 静电图像显影用调色剂、静电图像显影剂、调色剂盒、处理盒、成像装置和成像方法 |
CN108659607A (zh) * | 2017-03-27 | 2018-10-16 | 佳能株式会社 | 颜料分散体、调色剂的制造方法、水性墨和叠氮化合物 |
CN109971211A (zh) * | 2017-12-01 | 2019-07-05 | 山阳色素株式会社 | 颜料组合物 |
CN111039812A (zh) * | 2020-01-13 | 2020-04-21 | 肥城岳海化工有限公司 | 一种微通道连续法制备色酚as-ol的方法 |
CN111607247A (zh) * | 2020-06-16 | 2020-09-01 | 杭州百合科莱恩颜料有限公司 | 一种混晶型色酚as有机颜料及其制备方法 |
CN111679560A (zh) * | 2019-03-11 | 2020-09-18 | 富士施乐株式会社 | 静电荷像显影用色粉、静电荷像显影剂及色粉盒 |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5134794B2 (ja) * | 2006-08-22 | 2013-01-30 | 東京色材工業株式会社 | 変異原性の低減されたナフトール系アゾ顔料組成物およびその製造方法 |
JP2010195909A (ja) * | 2009-02-25 | 2010-09-09 | Toyo Ink Mfg Co Ltd | 顔料組成物およびインクジェット印刷用インキ |
JP5327399B1 (ja) * | 2012-05-21 | 2013-10-30 | 東洋インキScホールディングス株式会社 | 顔料組成物とその製造方法、それを用いた着色組成物、カラーフィルタ |
WO2014002335A1 (ja) | 2012-06-26 | 2014-01-03 | 保土谷化学工業株式会社 | カラーフィルター用キサンテン系色素並びに該色素を用いたカラーフィルター |
WO2016152636A1 (ja) | 2015-03-24 | 2016-09-29 | 保土谷化学工業株式会社 | キサンテン系染料を含有する青色系着色組成物、カラーフィルター用着色剤およびカラーフィルター |
US10472532B2 (en) * | 2015-03-31 | 2019-11-12 | Toyo Ink Sc Holdings Co., Ltd. | Magenta ink for ink-jet recording |
DE102015211827A1 (de) | 2015-06-25 | 2016-12-29 | Clariant International Ltd | Neue Naphthol AS-Pigmente |
DE102015211829A1 (de) | 2015-06-25 | 2016-12-29 | Clariant International Ltd | Verwendung von neuen Naphthol AS-Pigment-Mischungen in Printing-Materialien |
EP3181642A1 (en) | 2015-12-14 | 2017-06-21 | Cappelle Pigments nv | Method for manufacturing azoic pigments |
JP6065149B1 (ja) | 2016-06-01 | 2017-01-25 | コニカミノルタ株式会社 | 静電荷像現像用トナー |
JP6763213B2 (ja) * | 2016-06-29 | 2020-09-30 | Dic株式会社 | 新規アゾ化合物 |
CN110997822B (zh) | 2017-06-29 | 2023-01-03 | 保土谷化学工业株式会社 | 含有呫吨系染料的着色组合物、滤色器用着色剂和滤色器 |
DK3434737T3 (da) | 2017-07-26 | 2023-03-27 | Evonik Operations Gmbh | Modificerede pigmenter og deres anvendelse |
JP6368844B1 (ja) | 2017-08-25 | 2018-08-01 | 東洋インキScホールディングス株式会社 | アゾ顔料、カラーフィルタ用着色剤、着組成物およびカラーフィルタ |
KR20200072468A (ko) | 2017-10-24 | 2020-06-22 | 호도가야 가가쿠 고교 가부시키가이샤 | 크산텐계 카티온 염료와 유기 아니온으로 이루어지는 조염 화합물을 함유하는 착색 조성물, 컬러 필터용 착색제 및 컬러 필터 |
US10599060B2 (en) | 2017-12-06 | 2020-03-24 | Canon Kabushiki Kaisha | Toner |
JP7283887B2 (ja) | 2018-01-16 | 2023-05-30 | 保土谷化学工業株式会社 | キサンテン系カチオン染料とアニオン染料からなる造塩化合物を含有する着色組成物、カラーフィルター用着色剤およびカラーフィルター |
CN110511593B (zh) | 2018-05-21 | 2022-07-08 | 东洋油墨Sc控股株式会社 | 偶氮颜料、彩色滤光片及用于其的着色剂与着色组合物、以及包含其的显示装置与摄像元件 |
CN112048215A (zh) | 2019-06-05 | 2020-12-08 | 株式会社理光 | 墨水以及印刷方法 |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2533603A1 (de) * | 1975-07-26 | 1977-02-10 | Bayer Ag | Herstellung von azofarbstoffen unter zerkleinerung |
US4159264A (en) * | 1975-08-09 | 1979-06-26 | Ciba-Geigy Corporation | Automatic control of azo coupling processes in the manufacture of azo pigments |
GB2014597A (en) * | 1978-02-14 | 1979-08-30 | Ici Ltd | Continuous Coupling Process |
GB2021132B (en) * | 1978-02-14 | 1982-07-21 | Ici Ltd | Azo coupling process |
CH655125A5 (de) * | 1983-09-21 | 1986-03-27 | Ciba Geigy Ag | Verfahren zur herstellung von azofarbstoffpraeparaten. |
CH660494B (zh) * | 1984-12-12 | 1987-04-30 | ||
DE3926466C2 (de) * | 1989-08-10 | 1996-12-19 | Christoph Dipl Ing Caesar | Mikroreaktor zur Durchführung chemischer Reaktionen von zwei chemischen Stoffen mit starker Wärmetönung |
DE50100960D1 (de) * | 2000-02-09 | 2003-12-18 | Clariant Internat Ltd Muttenz | Verfahren zur herstellung von azofarbmitteln in mikroreaktoren |
US6432192B1 (en) * | 2000-02-23 | 2002-08-13 | Flint Ink Corporation | Process for manufacturing pigments |
DE10049200A1 (de) * | 2000-10-05 | 2002-04-11 | Clariant Gmbh | Verfahren zur Herstellung von Azofarbmitteln |
DE10143189A1 (de) * | 2001-09-04 | 2003-03-20 | Clariant Gmbh | Verfahren und Vorrichtung zur prozeßbegleitenden Reinigung von Mikro-und Minireaktoren |
JP2003162097A (ja) * | 2001-11-26 | 2003-06-06 | Kyocera Mita Corp | 正帯電マゼンタトナー |
JP3963795B2 (ja) * | 2002-07-09 | 2007-08-22 | 大日精化工業株式会社 | トナー |
JP3891280B2 (ja) * | 2002-07-26 | 2007-03-14 | 日本ゼオン株式会社 | マゼンタトナー |
JP2004070005A (ja) * | 2002-08-06 | 2004-03-04 | Kao Corp | レッドトナー |
JP2004117649A (ja) * | 2002-09-25 | 2004-04-15 | Dainippon Ink & Chem Inc | 赤色トナー |
-
2004
- 2004-04-22 DE DE102004019560A patent/DE102004019560A1/de not_active Withdrawn
-
2005
- 2005-04-06 EP EP05716543A patent/EP1740658A1/de not_active Withdrawn
- 2005-04-06 WO PCT/EP2005/003598 patent/WO2005105928A1/de active Application Filing
- 2005-04-06 CA CA002563812A patent/CA2563812A1/en not_active Abandoned
- 2005-04-06 BR BRPI0510073-9A patent/BRPI0510073A/pt not_active Application Discontinuation
- 2005-04-06 CN CNA2005800124906A patent/CN1946811A/zh active Pending
- 2005-04-06 JP JP2007508754A patent/JP2007533802A/ja active Pending
- 2005-04-06 KR KR1020067021744A patent/KR20060135896A/ko not_active Application Discontinuation
- 2005-04-06 US US11/578,739 patent/US20070240618A1/en not_active Abandoned
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103421345A (zh) * | 2012-05-21 | 2013-12-04 | 东洋油墨Sc控股株式会社 | 颜料组合物、其制造方法、着色组合物以及滤色器 |
TWI573841B (zh) * | 2012-05-21 | 2017-03-11 | 東洋油墨Sc控股股份有限公司 | 顏料組成物、其製造方法、著色組成物及濾色器 |
CN103424987A (zh) * | 2012-05-21 | 2013-12-04 | 东洋油墨Sc控股株式会社 | 滤色器用着色组合物以及滤色器 |
CN106257332B (zh) * | 2015-06-19 | 2019-11-12 | 富士施乐株式会社 | 静电图像显影用调色剂、静电图像显影剂、调色剂盒、处理盒、成像装置和成像方法 |
CN106257332A (zh) * | 2015-06-19 | 2016-12-28 | 富士施乐株式会社 | 静电图像显影用调色剂、静电图像显影剂、调色剂盒、处理盒、成像装置和成像方法 |
CN105524484A (zh) * | 2016-01-14 | 2016-04-27 | 上虞市新利化工有限公司 | 一种c.i.颜料红176的制备方法 |
CN105524484B (zh) * | 2016-01-14 | 2018-04-10 | 上虞市新利化工有限公司 | 一种c.i.颜料红176的制备方法 |
CN108659607A (zh) * | 2017-03-27 | 2018-10-16 | 佳能株式会社 | 颜料分散体、调色剂的制造方法、水性墨和叠氮化合物 |
CN108659607B (zh) * | 2017-03-27 | 2022-05-13 | 佳能株式会社 | 颜料分散体、调色剂的制造方法、水性墨和叠氮化合物 |
CN109971211A (zh) * | 2017-12-01 | 2019-07-05 | 山阳色素株式会社 | 颜料组合物 |
CN109971211B (zh) * | 2017-12-01 | 2021-11-30 | 山阳色素株式会社 | 颜料组合物 |
CN111679560A (zh) * | 2019-03-11 | 2020-09-18 | 富士施乐株式会社 | 静电荷像显影用色粉、静电荷像显影剂及色粉盒 |
CN111039812A (zh) * | 2020-01-13 | 2020-04-21 | 肥城岳海化工有限公司 | 一种微通道连续法制备色酚as-ol的方法 |
CN111039812B (zh) * | 2020-01-13 | 2023-01-06 | 泰安岳海新材料股份有限公司 | 一种微通道连续法制备色酚as-ol的方法 |
CN111607247A (zh) * | 2020-06-16 | 2020-09-01 | 杭州百合科莱恩颜料有限公司 | 一种混晶型色酚as有机颜料及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
US20070240618A1 (en) | 2007-10-18 |
EP1740658A1 (de) | 2007-01-10 |
WO2005105928A1 (de) | 2005-11-10 |
BRPI0510073A (pt) | 2007-10-16 |
CA2563812A1 (en) | 2005-11-10 |
KR20060135896A (ko) | 2006-12-29 |
DE102004019560A1 (de) | 2005-11-10 |
JP2007533802A (ja) | 2007-11-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1946811A (zh) | 高纯度萘酚as颜料 | |
CN1942529A (zh) | 高纯度偶氮着色剂的制备方法 | |
CN100424137C (zh) | 有机颜料的调理 | |
CN1298786C (zh) | 进行化学和物理工艺的方法和设备 | |
US7309389B2 (en) | Preparation of azo colorants in microreactors and their use in electrophotographic toners and developers, powder coatings, ink jet inks and electronic medias | |
CN1080292C (zh) | 制备喹丫啶酮颜料的方法 | |
CN1705719A (zh) | 酞菁颜料制剂 | |
JP3981396B2 (ja) | 水系顔料分散体の製造方法 | |
CN1814680A (zh) | 荧光着色剂组合物、着色方法和着色制品 | |
CN1305971C (zh) | 双偶氮颜料的制备方法 | |
JP4956917B2 (ja) | 水性顔料分散体および水性顔料記録液 | |
CN1890327A (zh) | 基于c.i.颜料黄74的单偶氮颜料制剂 | |
CN101831196B (zh) | 具有改进的可分散性的c.i.颜料红112 | |
CN101089051A (zh) | ε型铜酞菁颜料、其制造方法和着色组合物 | |
JP2006282758A (ja) | 紫外線硬化型インクジェット記録用イエロー色インク組成物 | |
CN1458965A (zh) | 偶氮橙颜料组合物 | |
KR100962922B1 (ko) | 불용성 아조 안료의 제조방법 및 그 제조장치 | |
JP6854782B2 (ja) | 新規ナフトールas顔料 | |
JP4495050B2 (ja) | 不溶性アゾ顔料の製造方法およびその製造装置 | |
EP1972662A2 (en) | Organic pigment fine particles and an organic pigment fine particle dispersion, method of producing an organic pigment fine particle dispersion | |
JP2006028341A (ja) | ジスアゾ顔料の製造方法及びジスアゾ顔料 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
WD01 | Invention patent application deemed withdrawn after publication |
Open date: 20070411 |