KR101620843B1 - pigment additives, their preparation and compositions containing the same - Google Patents
pigment additives, their preparation and compositions containing the same Download PDFInfo
- Publication number
- KR101620843B1 KR101620843B1 KR1020140039535A KR20140039535A KR101620843B1 KR 101620843 B1 KR101620843 B1 KR 101620843B1 KR 1020140039535 A KR1020140039535 A KR 1020140039535A KR 20140039535 A KR20140039535 A KR 20140039535A KR 101620843 B1 KR101620843 B1 KR 101620843B1
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- aryl
- pigment
- group
- arylamino
- 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
- 239000000049 pigment Substances 0.000 title claims abstract description 137
- 239000000203 mixture Substances 0.000 title claims abstract description 75
- 239000000654 additive Substances 0.000 title claims abstract description 57
- 238000002360 preparation method Methods 0.000 title description 7
- 239000006185 dispersion Substances 0.000 claims abstract description 62
- 230000000996 additive effect Effects 0.000 claims abstract description 54
- 238000000034 method Methods 0.000 claims abstract description 23
- 125000003118 aryl group Chemical group 0.000 claims description 36
- -1 monoalkylamino Chemical group 0.000 claims description 29
- 239000012860 organic pigment Substances 0.000 claims description 27
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 125000001769 aryl amino group Chemical group 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 16
- 239000012954 diazonium Substances 0.000 claims description 16
- 150000001989 diazonium salts Chemical class 0.000 claims description 16
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 10
- 125000004986 diarylamino group Chemical group 0.000 claims description 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 235000010288 sodium nitrite Nutrition 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 150000004056 anthraquinones Chemical class 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 claims description 2
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 claims 1
- 230000003287 optical effect Effects 0.000 abstract description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 229920005989 resin Polymers 0.000 description 17
- 239000011347 resin Substances 0.000 description 17
- 238000003756 stirring Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000002270 dispersing agent Substances 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- 235000002639 sodium chloride Nutrition 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- MBJAPGAZEWPEFB-UHFFFAOYSA-N 5-amino-2-(4-amino-2-sulfophenyl)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1C1=CC=C(N)C=C1S(O)(=O)=O MBJAPGAZEWPEFB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000003801 milling Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- LSPMHHJCDSFAAY-UHFFFAOYSA-N 2,6-dichloro-4-methylpyridine-3-carbonitrile Chemical compound CC1=CC(Cl)=NC(Cl)=C1C#N LSPMHHJCDSFAAY-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000001054 red pigment Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- PEOFTKOVYVXAMQ-UHFFFAOYSA-N 4-methyl-2,6-bis(2,4,6-trimethylanilino)pyridine-3-carbonitrile Chemical compound CC1=CC(C)=CC(C)=C1NC1=CC(C)=C(C#N)C(NC=2C(=CC(C)=CC=2C)C)=N1 PEOFTKOVYVXAMQ-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000000889 atomisation Methods 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000011247 coating layer Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000001056 green pigment Substances 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920006122 polyamide resin Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000009719 polyimide resin Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000011164 primary particle Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000001057 purple pigment Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 229920006337 unsaturated polyester resin Polymers 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 239000001052 yellow pigment Substances 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- NBUKAOOFKZFCGD-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)F NBUKAOOFKZFCGD-UHFFFAOYSA-N 0.000 description 1
- MWGUZDJVOZCARW-UHFFFAOYSA-N 2,6-bis(2,6-diethylanilino)-4-methylpyridine-3-carbonitrile Chemical compound CCC1=CC=CC(CC)=C1NC1=CC(C)=C(C#N)C(NC=2C(=CC=CC=2CC)CC)=N1 MWGUZDJVOZCARW-UHFFFAOYSA-N 0.000 description 1
- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- BXUYHLOOAOXULR-UHFFFAOYSA-N 2-ethoxyhexyl acetate Chemical compound CCCCC(OCC)COC(C)=O BXUYHLOOAOXULR-UHFFFAOYSA-N 0.000 description 1
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
- GGDYAKVUZMZKRV-UHFFFAOYSA-N 2-fluoroethanol Chemical compound OCCF GGDYAKVUZMZKRV-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 1
- CWJQQASJVVAXKL-UHFFFAOYSA-N 4-(3-Methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonic acid Chemical compound O=C1CC(C)=NN1C1=CC=C(S(O)(=O)=O)C=C1 CWJQQASJVVAXKL-UHFFFAOYSA-N 0.000 description 1
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 1
- TYCNXOAPQGVAQU-UHFFFAOYSA-N 5-oxo-1-(4-sulfophenyl)-4h-pyrazole-3-carboxylic acid Chemical compound O=C1CC(C(=O)O)=NN1C1=CC=C(S(O)(=O)=O)C=C1 TYCNXOAPQGVAQU-UHFFFAOYSA-N 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- NEDSWGQLHDMMFD-UHFFFAOYSA-N C(CCCCC)NC1=C(C#N)C(=CC(=N1)NCCCCCC)C Chemical compound C(CCCCC)NC1=C(C#N)C(=CC(=N1)NCCCCCC)C NEDSWGQLHDMMFD-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/16—Disazo dyes from other coupling components
-
- 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
- C09B67/006—Preparation of organic pigments
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Organic Chemistry (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Optical Filters (AREA)
Abstract
본 발명은 신규한 안료 첨가제, 이의 제조방법 및 이를 포함하는 안료 분산 조성물에 관한 것으로 본 발명의 안료 분산 조성물은 본 발명의 안료 첨가제를 포함하여 광학적 특성, 분산성 및 분산 안정성이 매우 높다.The present invention relates to a novel pigment additive, a process for producing the same, and a pigment dispersion composition containing the same, wherein the pigment dispersion composition of the present invention contains the pigment additive of the present invention and has excellent optical properties, dispersibility and dispersion stability.
Description
본 발명은 신규한 안료 첨가제, 이의 제조방법 및 이를 포함하는 안료 분산 조성물에 관한 것으로, 보다 상세하게는 디페닐렌 양쪽에 아조기를 가지는 안료 첨가제, 이의 제조방법, 이를 포함하는 안료 분산 조성물에 관한 것이다.The present invention relates to a novel pigment additive, a process for producing the same, and a pigment dispersion composition containing the same, and more particularly, to a pigment additive having an azo group on both diphenylenes, a process for producing the same, and a pigment dispersion composition containing the same .
액정컬러디스플레이, 촬상 소자 등의 제조에 사용되는 컬러필터는 감광성 수지액 중에 적색(R), 녹색(G), 및 청색(B)의 삼색의 안료를 각각 분산시킨 컬러필터용 안료 분산 조성물을 도포하여 착색피막을 형성하고, 착색피막에 포토마스크를 이용하여 노광, 현상하여 착색피막을 패턴화하는 방식으로 원하는 화소를 형성하는 방법으로 제조된다.The color filter used in the production of liquid crystal color display and image pickup device is made by applying a pigment dispersion composition for a color filter in which three colors of red (R), green (G), and blue (B) To form a colored film, and the colored film is exposed and developed by using a photomask to form a desired colored film by patterning the colored film.
컬러필터용 안료 분산 조성물에 요구되는 특성으로는 고 휘도, 착색력 및 고 명암비 등의 우수한 광학적 성질과 분산성, 저장 안정성이 요구된다. 이러한 특성을 만족시키기 위한 안료 분산 조성물을 제조하기 위해서는 100 nm이하의 미세한 안료입자가 균일한 분포도를 가지며 분산되어야 한다. Properties required for a pigment dispersion composition for a color filter are required to have excellent optical properties such as high luminance, coloring power and high contrast ratio, dispersibility, and storage stability. In order to prepare a pigment dispersion composition for satisfying such characteristics, fine pigment particles of 100 nm or less must be dispersed with a uniform distribution.
컬러필터용 안료 분산 조성물에 적합한 미세 안료를 얻기 위한 종래의 주요 기술로 소금을 이용하여 안료 입자를 미세화 시키는 솔트 밀링(salt milling)이 있으며, 이 방법을 이용하여 원하는 입도와 분포도를 갖는 미세 안료를 제조하여 고 휘도, 착색력 및 고 명암비 등의 광학적 성질을 향상 시켜왔다. As a conventional technique for obtaining a fine pigment suitable for a pigment dispersion composition for a color filter, there is a salt milling method in which pigment particles are finely dispersed using salt, and a fine pigment having a desired particle size and distribution is obtained by using this method To improve optical properties such as high luminance, tinting strength and high contrast ratio.
그러나 안료가 미세화되면 안료입자 자체의 재 응집력이 강해져, 안료의 분산성 및 분산 안정성이 나빠지게 되어 문제가 있다. 이를 해결하기 위해, 분산제 등을 사용한 기술도 알려져 있지만, 상기 용도에서 요구되는 특성을 얻기에는 아직 불충분하다. However, if the pigment becomes finer, the coagulation power of the pigment particle itself becomes strong, and the dispersibility and dispersion stability of the pigment become poor, which is problematic. To solve this problem, a technique using a dispersing agent or the like is known, but it is still insufficient to obtain the properties required in the above applications.
따라서, 고 휘도, 착색력 및 고 명암비 등의 광학적 성질을 만족할 뿐만 아니라 고 분산성 및 분산 안정성을 충분히 만족시킬 수 있는 안료 분산 조성물의 첨가제 개발이 요구된다. Therefore, it is required to develop an additive for a pigment dispersion composition that not only satisfies optical properties such as high luminance, tinting strength and high contrast ratio but also satisfies high dispersibility and dispersion stability.
본 발명은 안료 분산 조성물의 광학적 특성과 분산성 및 분산 안정성을 높일 수 있는 안료 첨가제 및 이의 제조방법을 제공한다.The present invention provides a pigment additive capable of enhancing optical properties, dispersibility, and dispersion stability of a pigment dispersion composition and a method for producing the same.
또한 본 발명은 본 발명의 안료 첨가제를 포함하는 안료 분산 조성물을 제공한다.The present invention also provides a pigment dispersion composition comprising the pigment additive of the present invention.
또한 본 발명은 본 발명의 안료 분산 조성물을 포함하는 컬러 레지스트 조성물 및 이를 이용하여 제조되는 컬러필터를 제공한다.The present invention also provides a color resist composition comprising the pigment dispersion composition of the present invention and a color filter manufactured using the same.
본 발명은 고휘도와 고명암비를 가지며 분산성과 분산 안정성이 뛰어난 안료 분산 조성물을 제조하기 위한 신규한 안료 첨가제를 제공한다.The present invention provides a novel pigment additive for producing a pigment dispersion composition having high brightness and high contrast ratio and excellent dispersibility and dispersion stability.
본 발명의 안료 첨가제는 하기 화학식 1로 표시된다.The pigment additive of the present invention is represented by the following general formula (1).
[화학식 1] [Chemical Formula 1]
[상기 화학식 1에서, [In the above formula (1)
A는 
R1은 수소, (C1-C30)알킬, (C3-C30)시클로알킬, (C3-C30)헤테로시클로알킬, (C1-C30)알콕시, (C6-C30)아릴, (C6-C30)아르(C1-C30)알킬, (C3-C30)헤테로아릴, (C6-C30)아릴옥시, (C1-C30)알킬옥시, 모노(C1-C30)알킬아미노, 디(C1-C30)알킬아미노, 모노(C6-C30)아릴아미노, 디(C6-C30)아릴아미노, (C1-C30)알킬카보닐, 카르복실산기, 술포닐, 할로겐, 아미노, 시아노 또는 니트로이며,R 1 is hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, (C3-C30) heterocycloalkyl, (C1-C30) alkoxy, (C6-C30) aryl, (C6-C30) ar ( (C1-C30) alkyl, (C3-C30) heteroaryl, (C6-C30) aryloxy, (C6-C30) arylamino, di (C6-C30) arylamino, (C1-C30) alkylcarbonyl, carboxylic acid group, sulfonyl, halogen, amino, cyano or nitro,
o는 1 내지 3의 정수이며,o is an integer from 1 to 3,
p는 1 내지 2의 정수이며;p is an integer of 1 to 2;
M은 Na, H, K 또는 Li이며;M is Na, H, K, or Li;
B는 수소, 아미노, (C1-C30)알킬, (C1-C30)알콕시, (C6-C30)아릴, 모노(C1-C30)알킬아미노, 디(C1-C30)알킬아미노, 모노(C6-C30)아릴아미노 또는 디(C6-C30)아릴아미노이며;B is selected from the group consisting of hydrogen, amino, (C 1 -C 30) alkyl, (C 1 -C 30) alkoxy, (C 6 -C 30) aryl, mono (C 1 -C 30) alkylamino, ) Arylamino or di (C6-C30) arylamino;
상기 R1의 알킬, 시클로알킬, 헤테로시클로알킬, 알콕시, 아릴, 아르알킬, 헤테로아릴, 아릴옥시, 알킬옥시, 모노알킬아미노, 디알킬아미노, 모노아릴아미노, 디아릴아미노 및 알킬카보닐과 B의 알킬, 알콕시, 아릴, 모노알킬아미노, 디알킬아미노, 모노아릴아미노 및 디아릴아미노는 할로겐, 카르복실산기, 술포닐, 시아노, 니트로, 히드록시, (C1-C30)알킬, (C6-C30)아릴, (C3-C30)헤테로아릴에서 선택되는 어느 하나이상으로 더 치환될 수 있다.]Wherein R 1 is selected from the group consisting of alkyl, cycloalkyl, heterocycloalkyl, alkoxy, aryl, aralkyl, heteroaryl, aryloxy, alkyloxy, monoalkylamino, dialkylamino, monoarylamino, diarylamino and alkylcarbonyl and B (C1-C30) alkyl, (C6-C30) alkyl, alkoxy, aryl, monoalkylamino, dialkylamino, monoarylamino, and diarylamino groups are optionally substituted with one or more substituents selected from the group consisting of halogen, carboxylic acid group, sulfonyl, cyano, nitro, C30) aryl, (C3-C30) heteroaryl, and the like.
본 발명의 안료 첨가제는 디아조 화합물로 술폰산기 또는 술포네이트기로 치환된 바이페닐렌 양쪽에 아조기를 가져 우수한 휘도와 명암비를 가질 수 있으며, 바이페닐렌기에 치환된 술폰산기 또는 술포네이트기를 가져 이를 첨가제로 포함하는 안료 분산 조성물의 분산성과 분산 안정성을 높인다.The pigment additive of the present invention has azo groups on both sides of biphenylene substituted with a sulfonic acid group or sulfonate group as a diazo compound and can have excellent brightness and contrast ratio and has sulfonic acid group or sulfonate group substituted in biphenylene group, To improve dispersibility and dispersion stability of the pigment dispersion composition.
뿐만 아니라 아조기 양쪽에 다양한 치환기, 구체적으로 상기 화학식 1에서 A와 B를 다양한 치환기로 변환시켜 안료 분산 조성물의 광학적 특성뿐만 아니라 용해도, 분산성등의 물리적 특성을 조절할 수 있는 장점이 있다.In addition, it is possible to control various physical properties such as solubility and dispersibility as well as optical properties of the pigment dispersion composition by converting various substituents on both azo groups, specifically, A and B in the above formula (1) into various substituents.
본 발명의 안료 첨가제를 포함하는 안료 분산 조성물이 우수한 광학적 특성을 가지기위한 측면에서 바람직하게 본 발명의 일 실시예에 따른 상기 화학식 1에서 R1은 서로 독립적으로 (C1-C30)알킬, (C6-C30)아릴, (C6-C30)아르(C1-C30)알킬, 모노(C1-C30)알킬아미노, 디(C1-C30)알킬아미노, 모노(C6-C30)아릴아미노, 디(C6-C30)아릴아미노, (C1-C30)알킬카보닐, 카르복실산기, 술포닐, 할로겐, 시아노, 아미노 또는 니트로이며;In a preferred embodiment of the present invention, R 1 in the formula ( 1) is independently selected from the group consisting of (C 1 -C 30) alkyl, (C 6 -C 30) (C6-C30) aryl, (C6-C30) aryl (C1-C30) alkyl, mono Arylamino, (C1-C30) alkylcarbonyl, carboxylic acid group, sulfonyl, halogen, cyano, amino or nitro;
상기 R1의 알킬, 아릴, 아르알킬, 모노알킬아미노, 디알킬아미노, 모노아릴아미노 및 디아릴아미노은 할로겐, 카르복실산기, 술포닐, 시아노, 니트로, 히드록시, (C1-C30)알킬, (C6-C30)아릴, (C3-C30)헤테로아릴에서 선택되는 어느 하나이상으로 더 치환될 수 있다.Alkyl of said R 1, aryl, aralkyl, monoalkylamino, dialkylamino, mono-arylamino and diarylamino ahminoeun halogen, carboxylic acid group, a sulfonyl, cyano, nitro, hydroxy, (C1-C30) alkyl, (C6-C30) aryl, (C3-C30) heteroaryl, and the like.
보다 바람직하게 본 발명의 일 실시예에 따른 상기 화학식 1은 하기 화학식 2 또는 화학식 3으로 표시될 수 있다.More preferably, Formula 1 according to an embodiment of the present invention may be represented by Formula 2 or Formula 3 below.
[화학식 2] (2)
[화학식 3] (3)
[상기 화학식 2 및 3에서,[In the above formulas (2) and (3)
R11 내지 R12 및 R15는 서로 독립적으로 수소, (C1-C30)알킬, (C6-C30)아릴, 또는 (C6-C30)아르(C1-C30)알킬이며;R 11 to R 12 and R 15 are independently of each other hydrogen, (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 6 -C 30) aryl (C 1 -C 30) alkyl;
R13 및 R14는 서로 독립적으로 수소, (C1-C30)알킬 또는 카르복실산기이며;R 13 and R 14 are, independently of each other, hydrogen, (C 1 -C 30) alkyl or a carboxylic acid group;
상기 R11 내지 R12 및 R15의 알킬, 아릴 및 아르알킬과 R13 및 R14의 알킬은 할로겐, 카르복실산기, 술포닐, 시아노, 니트로, 히드록시, (C1-C30)알킬, (C6-C30)아릴, (C3-C30)헤테로아릴에서 선택되는 어느 하나이상으로 더 치환될 수 있다.]The alkyl, aryl and aralkyl of R 11 to R 12 and R 15 and the alkyl of R 13 and R 14 are independently selected from the group consisting of halogen, carboxylic acid group, sulfonyl, cyano, nitro, hydroxy, (C 1 -C 30) C6-C30) aryl, (C3-C30) heteroaryl, and the like.
상기 화학식 2 또는 3으로 표시되는 본 발명의 안료 첨가제는 고리내 포함된 질소원자 또는 아미노기를 가져 이를 포함하는 안료 분산 조성물의 광학적 특성뿐만 아니라 용해도와 분산성을 높일 수 있다.
The pigment additive of the present invention represented by the above general formula (2) or (3) has a nitrogen atom or an amino group contained in the ring and can increase the solubility and dispersibility as well as the optical properties of the pigment dispersion composition containing the nitrogen atom or amino group.
구체적으로 본 발명의 일 실시예에 따른 안료 첨가제는 하기 화합물에서 선택될 수 있으나, 이에 한정이 있는 것은 아니다. Specifically, the pigment additive according to one embodiment of the present invention may be selected from the following compounds, but is not limited thereto.
본 발명에 기재된 본 발명에 기재된 「알킬」, 「알콕시」 및 그 외 「알킬」부분을 포함하는 치환체는 직쇄 또는 분쇄 형태를 모두 포함한다. The substituents including the "alkyl", "alkoxy" and other "alkyl" moieties described in the present invention described in the present invention include both linear and branched forms.
또한 본 발명에 기재된 「아릴」은 하나의 수소 제거에 의해서 방향족 탄화수소로부터 유도된 유기 라디칼로, 각 고리에 적절하게는 4 내지 7개, 바람직하게는 5 또는 6개의 고리원자를 포함하는 단일 또는 융합고리계를 포함하며, 다수개의 아릴이 단일결합으로 연결되어 있는 형태까지 포함한다. 구체적인 예로 페닐, 나프틸, 비페닐, 안트릴, 인데닐(indenyl), 플루오레닐 등을 포함하지만, 이에 한정되지 않는다. The term " aryl " in the present invention means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, and may be a single or fused ring containing 4 to 7, preferably 5 or 6 ring atoms, A ring system, and a form in which a plurality of aryls are connected by a single bond. Specific examples include, but are not limited to, phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, and the like.
본 발명에 기재된 「헤테로아릴」은 방향족 고리 골격 원자로서 B, N, O, S, P(=O), Si 및 P로부터 선택되는 1 내지 4개의 헤테로원자를 포함하고, 나머지 방향족 고리 골격 원자가 탄소인 아릴 그룹을 의미하는 것으로, 5 내지 6원 단환 헤테로아릴, 및 하나 이상의 벤젠환과 축합된 다환식 헤테로아릴이며, 부분적으로 포화될 수도 있다. 또한, 본 발명에서의 헤테로아릴은 하나 이상의 헤테로아릴이 단일결합으로 연결된 형태도 포함한다. "Heteroaryl" in the present invention includes 1 to 4 heteroatoms selected from B, N, O, S, P (= O), Si and P as aromatic ring skeletal atoms and the remaining aromatic ring skeletal atoms are carbon Means a 5 to 6 membered monocyclic heteroaryl and a polycyclic heteroaryl condensed with at least one benzene ring and may be partially saturated. The heteroaryl in the present invention also includes a form in which one or more heteroaryl is connected to a single bond.
본 발명에 기재된 단독으로 또는 또 다른 기의 일부분으로서 기재된 「시클로알킬」은 3 내지 9개의 탄소 원자의 완전히 포화 및 부분적으로 불포화된 탄화수소 고리를 의미하며, 아릴 또는 헤테로아릴이 융합되어 있는 경우도 포함된다. &Quot; Cycloalkyl ", alone or as part of another group described in the present invention, refers to a fully saturated and partially unsaturated hydrocarbon ring of 3 to 9 carbon atoms, inclusive of the fused aryl or heteroaryl do.
본 발명에 기재된「헤테로시클로알킬」은 헤테로원자로서 고리 내에 산소, 황 또는 질소를 포함하는 완전히 포화 및 부분적으로 불포화된 탄화수소 고리를 의미하며, 헤테로원자의 개수는 1-4이며, 바람직하게는 1-2이다. 헤테로시클로알킬에서 시클로알킬은 바람직하게는 모노시클로알킬 또는 비시클로알킬이며, 방향족고리리인 아릴 또는 헤테로아릴이 융합되어 있는 경우도 포함하며, 이중결합 또는 삼중결합으로 연결되어 있는 경우도 포함된다."Heterocycloalkyl" in the present invention means a fully saturated and partially unsaturated hydrocarbon ring containing oxygen, sulfur or nitrogen as a heteroatom in the ring, the number of heteroatoms being 1-4, preferably 1 -2. Cycloalkyl in heterocycloalkyl is preferably monocycloalkyl or bicycloalkyl, including those in which an aromatic cyclic aryl or heteroaryl is fused and also includes a double bond or a triple bond.
또한 본 발명은 본 발명의 안료 첨가제의 제조방법을 제공한다.The present invention also provides a process for preparing the pigment additive of the present invention.
본 발명의 안료 첨가제의 제조방법은 산 존재하에 하기 화학식 4와 아질산나트륨을 반응시켜 하기 화학식 4의 디아조늄염을 형성하는 단계; 및The method for preparing a pigment additive according to the present invention comprises the steps of: reacting a compound represented by the formula (4) with sodium nitrite in the presence of an acid to form a diazonium salt represented by the following formula (4); And
하기 화학식 4의 디아조늄염과 하기 화학식 5를 반응시켜 상기 화학식 1로 표시되는 안료 첨가제를 제조하는 단계;를 포함한다.Reacting a diazonium salt of the following formula (4) with a compound of the following formula (5) to prepare a pigment additive represented by the formula (1).
[화학식 4] [Chemical Formula 4]
[화학식 5][Chemical Formula 5]
[상기 화학식 화학식 4 내지 5에서,
[In the formulas (4) to (5)
A는 
R1은 수소, (C1-C30)알킬, (C3-C30)시클로알킬, (C3-C30)헤테로시클로알킬, (C1-C30)알콕시, (C6-C30)아릴, (C6-C30)아르(C1-C30)알킬, (C3-C30)헤테로아릴, (C6-C30)아릴옥시, (C1-C30)알킬옥시, 모노(C1-C30)알킬아미노, 디(C1-C30)알킬아미노, 모노(C6-C30)아릴아미노, 디(C6-C30)아릴아미노, (C1-C30)알킬카보닐, 카르복실산기, 술포닐, 할로겐, 아미노, 시아노 또는 니트로이며,R 1 is hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, (C3-C30) heterocycloalkyl, (C1-C30) alkoxy, (C6-C30) aryl, (C6-C30) ar ( (C1-C30) alkyl, (C3-C30) heteroaryl, (C6-C30) aryloxy, (C6-C30) arylamino, di (C6-C30) arylamino, (C1-C30) alkylcarbonyl, carboxylic acid group, sulfonyl, halogen, amino, cyano or nitro,
o는 1 내지 3의 정수이며,o is an integer from 1 to 3,
p는 1 내지 2의 정수이며;p is an integer of 1 to 2;
M은 Na, H, K 또는 Li이며;M is Na, H, K, or Li;
B는 수소, 아미노, (C1-C30)알킬, (C1-C30)알콕시, (C6-C30)아릴, 모노(C1-C30)알킬아미노, 디(C1-C30)알킬아미노, 모노(C6-C30)아릴아미노 또는 디(C6-C30)아릴아미노이며;B is selected from the group consisting of hydrogen, amino, (C 1 -C 30) alkyl, (C 1 -C 30) alkoxy, (C 6 -C 30) aryl, mono (C 1 -C 30) alkylamino, ) Arylamino or di (C6-C30) arylamino;
상기 R1의 알킬, 시클로알킬, 헤테로시클로알킬, 알콕시, 아릴, 아르알킬, 헤테로아릴, 아릴옥시, 알킬옥시, 모노알킬아미노, 디알킬아미노, 모노아릴아미노, 디아릴아미노 및 알킬카보닐과 B의 알킬, 알콕시, 아릴, 모노알킬아미노, 디알킬아미노, 모노아릴아미노 및 디아릴아미노는 할로겐, 카르복실산기, 술포닐, 시아노, 니트로, 히드록시, (C1-C30)알킬, (C6-C30)아릴, (C3-C30)헤테로아릴에서 선택되는 어느 하나이상으로 더 치환될 수 있다.]Wherein R 1 is selected from the group consisting of alkyl, cycloalkyl, heterocycloalkyl, alkoxy, aryl, aralkyl, heteroaryl, aryloxy, alkyloxy, monoalkylamino, dialkylamino, monoarylamino, diarylamino and alkylcarbonyl and B (C1-C30) alkyl, (C6-C30) alkyl, alkoxy, aryl, monoalkylamino, dialkylamino, monoarylamino, and diarylamino groups are optionally substituted with one or more substituents selected from the group consisting of halogen, carboxylic acid group, sulfonyl, cyano, nitro, C30) aryl, (C3-C30) heteroaryl, and the like.
본 발명의 일 실시예에 따른 상기 산은 염산, 황산, 질산, 인산 및 이들의 혼합산일 수 있으며, 반응효율면에서 바람직하게는 염산일 수 있다.The acid according to an embodiment of the present invention may be hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, or a mixed acid thereof, and may be hydrochloric acid in view of reaction efficiency.
본 발명의 일 실시에에 따른 상기 화학식 4 및 화학식 5는 유기합성분야에서 사용되는 반응으로 합성하거나 상업적으로 구입하여 사용될 수 있음은 물론이다.It is needless to say that the above-mentioned chemical formulas (4) and (5) according to one embodiment of the present invention can be synthesized as a reaction used in the field of organic synthesis or can be purchased commercially.
본 발명의 제조방법에서 사용되는 용매는 유기용매, 물 또는 이들의 혼합물일 수 있으며, 통상의 유기용이면 모두 가능하나, 에틸아세테이트(EA), 다이클로로메탄(DCM), 다이클로로에탄(DCE), 톨루엔(Toluene), 아세토나이트릴(MeCN), 나이트로 메탄(Nitromethan), 테트라하이드로퓨란(THF), N,N-다이메틸 포름아마이드 (DMF) 및 N,N-다이메틸아세트아마이드(DMA)로 이루어진 군으로부터 선택되는 1종 이상을 사용하는 것이 바람직하다.The solvent used in the production method of the present invention may be an organic solvent, water or a mixture thereof. Any organic solvent may be used, but ethyl acetate (EA), dichloromethane (DCM), dichloroethane (DCE) , toluene (toluene), acetonitrile (MeCN), nitro methane (Nitromethan), tetrahydrofuran (THF), N, N - dimethylformamide (DMF) and N, N - dimethylacetamide (DMA) Is preferably used.
본 발명의 반응온도는 통상의 유기합성에서 사용되는 온도에서 사용가능하나, 반응시간 반응물질 및 출발물질의 양에 따라 달라질 수 있으며, TLC 등을 통하여 출발물질이 완전히 소모됨을 확인한 후 반응을 완결시키도록 한다. 반응을 완결되면 통상의 유기합성에서 사용되는 방법으로 분리정제할 수 있으며, 일례로 추출과정 후 감압 하에서 용매를 증류시킨 후 관 크로마토그래피 등의 통상적인 방법을 통하여 목적물을 분리 정제할 수도 있다.Although the reaction temperature of the present invention can be used at a temperature used in conventional organic synthesis, it can be varied depending on the amount of the reaction material and the starting material, and it is confirmed through the TLC or the like that the starting material is completely consumed, . When the reaction is completed, it can be separated and purified by a method commonly used in organic synthesis. For example, after the extraction process, the solvent may be distilled off under reduced pressure, and the target product may be separated and purified through a conventional method such as column chromatography.
또한 본 발명은 본 발명의 신규한 안료 첨가제를 포함하는 안료 분산 조성물을 제공한다.The present invention also provides a pigment dispersion composition comprising the novel pigment additive of the present invention.
본 발명의 안료 분산 조성물은 본 발명의 안료 첨가제를 포함하여 휘도, 명암비등의 광학적 특성이 우수할 뿐만 아니라 분산성과 안정성이 우수하다.The pigment dispersion composition of the present invention is excellent in optical properties such as brightness and contrast ratio, as well as excellent dispersibility and stability, including the pigment additive of the present invention.
본 발명의 일 실시예에 따른 안료 분산 조성물은 본 발명의 안료 첨가제 및 유기 안료를 포함할 수 있으며, 유기 안료 100중량부에 대해서 0.1 내지 30중량부의 배합 비율이 바람직하고, 더 바람직하게는 1 내지 20질량부의 배합 비율이 좋다. 상기 안료 첨가제의 배합 비율이 너무 적으면, 목적으로 하는 효과를 충분히 얻기 어려워지며 상기의 배합 비율이 너무 많아도, 이에 비례하는 효과는 얻지 못하고, 안료 분산 조성물 및 이를 이용한 착색 조성물의 여러 가지 물성을 저하시켜, 본래의 색상을 크게 변화시는 요인이 된다.The pigment dispersion composition according to an embodiment of the present invention may include the pigment additive and the organic pigment of the present invention, and the blending ratio of 0.1 to 30 parts by weight is preferable for 100 parts by weight of the organic pigment, 20 parts by mass is preferable. If the compounding ratio of the pigment additive is too small, it is difficult to obtain a desired effect sufficiently, and if the compounding ratio is too large, the effect proportional thereto can not be obtained and the physical properties of the pigment dispersing composition and the coloring composition using the pigment are deteriorated Which causes the original color to largely change.
본 발명의 안료 분산 조성물에 포함되는 유기 안료는 특별히 제한되지 않으나, 아조계 안료, 프탈로시아닌계 안료, 퀴나크리돈계 안료, 페릴렌/페리논계 안료(perylene/perinone pigments), 이소인돌리논계 안료(isoindolinone pigments), 이소인돌린계 안료(isoindoline pigments), 디옥사진계 안료(dioxazine pigments), 퀴노프탈론계 안료(quinophthalone pigments), 디케토피롤로피롤계 안료(diketopyrrolopyrole pigments), 안트라퀴논계 안료(anthraquinone pigments), 티오인디고계 안료(thioindigo pigments) 및 금속 착체계 안료(metal complex pigments) 등에서 선택되는 하나이상일 수 있다.The organic pigments contained in the pigment dispersion composition of the present invention are not particularly limited, and examples thereof include azo pigments, phthalocyanine pigments, quinacridone pigments, perylene / perinone pigments, isoindolinone pigments pigments, isoindoline pigments, dioxazine pigments, quinophthalone pigments, diketopyrrolopyrole pigments, anthraquinone pigments, anthraquinone pigments, , Thioindigo pigments, and metal complex pigments. [0035] The term " pigments "
본 발명의 안료 분산 조성물은 적색, 녹색, 황색, 자색 안료등을 단독 또는 혼합하여 사용될 수 있다.The pigment dispersion composition of the present invention may be used alone or in combination of red, green, yellow, and purple pigments.
적색 안료의 경우 C.I. Pigment Red 7, 14, 48:1, 48:2, 48:3, 48:4, 81:1, 81:2, 81:3, 146, 177, 184, 185, 187, 200, 202, 208, 210, 246, 254, 255, 264, 270, 272 등을 사용할 수 있으며, 상기 녹색 안료의 경우 C.I. Pigment Green 7, 10, 36, 37등을 사용할 수 있고, 상기 청색 안료의 경우 C.I. Pigment Blue 15:1, 15:2, 15:3, 15:4, 15:6, 16, 80등을 사용할 수 있으며, 상기 황색 안료의 경우 C.I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 193, 194, 199, 213, 214 등을 사용할 수 있고, 상기 자색 안료의 경우 C.I. Pigment Violet 23, 34, 35, 37 등을 사용할 수 있으며, 이들을 단독으로 또는 2종 이상 혼합하여 사용할 수 있다.C.I. Pigment Red 7, 14, 48: 1, 48: 2, 48: 3, 48: 4, 81: 1, 81: 2, 81: 3, 146, 177, 184, 185, 187, 200, 210, 246, 254, 255, 264, 270, and 272 may be used. In the case of the green pigment, CI Pigment Green 7, 10, 36, 37 and the like can be used. In the case of the blue pigment, C.I. Pigment Blue 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 80 and the like. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35: 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 169, 170, 171, 172, 173, 193, 194, 199, 213 and 214 can be used. In the case of the purple pigment, CI Pigment Violet 23, 34, 35, 37 or the like may be used, and these may be used singly or in combination of two or more kinds.
특히, 적색 안료 분산 조성물의 경우에는 상기 유기 안료가, C.I. 피그먼트 레드 122, C.I. 피그먼트 레드 177, C.I. 피그먼트 레드 254 및 C.I. 피그먼트 바이올렛 19로부터 적어도 하나 이상 선택되는 것이 좋다. Particularly, in the case of the red pigment dispersion composition, the organic pigment is preferably selected from the group consisting of C.I. Pigment Red 122, C.I. Pigment Red 177, C.I. Pigment Red 254 and C.I. Pigment Violet < SEP > 19 < SEP >
상술한 유기 안료는 상기 안료 첨가제로 표면이 개질되는 바, 이는 밀링 등과 같은 분쇄 및 분산 과정을 통해 분쇄되어 미립화된 안료의 표면상에 상기 안료 첨가제가 결합하는 것을 의미하며, 이를 통해 상기 유기 안료의 성질을 개선하는 것이 가능해진다. 즉, 상기 안료 첨가제는 상기 유기 안료의 표면상에 코팅층을 형성하게 되며, 이는 연속 또는 비 연속상의 코팅층을 의미한다. 이와 같이 표면층을 형성하는 안료 첨가제를 통해 상기 유기 안료의 분산 안정성, 저장 안정성 및 컬러특성을 개선하는 것이 가능해진다. The organic pigments described above are surface-modified with the pigment additive, which means that the pigment additive binds on the surface of an atomized pigment which is pulverized through milling and dispersion processes such as milling, It becomes possible to improve the properties. That is, the pigment additive forms a coating layer on the surface of the organic pigment, which means a continuous or discontinuous coating layer. The dispersion stability, storage stability and color characteristics of the organic pigment can be improved through the pigment additive forming the surface layer.
상기 안료 첨가제의 잔기와 유기 안료는 동일한 계열을 사용하는 것이 좋으나 반드시 동일할 필요는 없으며, 반드시 동일한 색상을 나타내는 것을 조합할 필요는 없고, 필요에 따라서는 상이한 색상을 나타내는 물질을 사용하는 것도 가능하다. 즉 적색 안료에 황색 안료 첨가제로 표면을 개질하고 색 특성을 개선하는 것도 가능하며, 또한 동일한 색상을 갖는 유기 안료 및 안료 첨가제를 사용하여 색 순도를 개선하는 것도 또한 가능하다.It is preferable that the residue of the pigment additive and the organic pigment use the same series, but they do not necessarily have to be the same, and it is not always necessary to combine those having the same hue, and it is also possible to use a material exhibiting a different hue . That is, it is also possible to modify the surface of the red pigment with a yellow pigment additive to improve color characteristics, and it is also possible to improve the color purity by using organic pigments and pigment additives having the same color.
본 발명의 안료 분산 조성물은 본 발명의 안료 첨가제외에도 분산제를 사용할 수 있으며, 이와 같은 분산제로서는 제한되지 않으나, 고분자량 분산제를 사용하는 것이 바람직하다.The pigment dispersion composition of the present invention may contain a dispersant in addition to the pigment additive of the present invention. The dispersant is not limited to such a dispersant, but it is preferable to use a high molecular weight dispersant.
상기 고분자량 분산제로서는 바람직하게는 1,000 내지 100,000 범위내의 중량평균 분자량을 가지는 것을 사용할 수 있으며, 더욱 바람직하게는 10,000 내지 30,000의 중량평균분자량을 갖는 고분자량 분산제를 사용하는 것이 좋다. 이와 같은 고분자량 분산제로서는 시판중인 제품, 예를 들어 상품명 EFKA4046(EFKA사 제조), PB-821(Ajinomoto Fine Techno사 제조), BYK사의 디스퍼빅(DISPERBIK) 160, 161, 162, 163, 164, 182, 184(상품명), 아비시아사(Avecia Limited)의 소르스파스(SOLSPERSE) 22000, 24000, 28000(상품명), 쿠스모토 화성사의 디스바론(DISPARLON) DA-234, 325, 375, 725(상품명) 등을 들 수 있지만, 이들에 한정되지 않는다.The high molecular weight dispersant may preferably have a weight average molecular weight in the range of 1,000 to 100,000, and more preferably 10,000 to 30,000 in the high molecular weight dispersant. Examples of such a high molecular weight dispersant include commercially available products such as EFKA4046 (trade name, manufactured by EFKA), PB-821 (manufactured by Ajinomoto Fine Techno), DISPERBIK 160, 161, 162, 163, 164 and 182 , DISPARLON DA-234, 325, 375, 725 (trade name) of Auxia Limited, SOLSPERSE 22000, 24000, 28000 (trade name) , But are not limited thereto.
이와 같은 고분자량 분산제는 제한되지 않으나 상기 유기 안료 100중량부에 대하여 1 내지 30중량부의 함량으로 사용 할 수 있다. 상기 분산제 함량이 1중량부 미만이면 충분한 분산 효과를 얻을 수 없고, 30중량부를 초과하는 경우 경제성이 저하되어 바람직하지 않다. The high molecular weight dispersant is not limited, but may be used in an amount of 1 to 30 parts by weight based on 100 parts by weight of the organic pigment. If the content of the dispersant is less than 1 part by weight, a sufficient dispersing effect can not be obtained. If the amount is more than 30 parts by weight, economical efficiency is lowered.
안료 분산 조성물에는 수지가 더 포함될 수 있다. 일례로는 페트롤륨 수지, 카세인, 쉘락, 로진-변성 말레산 수지, 로진-변성페놀수지, 니트로셀룰로오스, 셀룰로오스아세테이트 부티레이트, 고리화 고무, 염소화 고무, 산화 고무, 염산 고무, 페놀 수지, 알키드 수지, 폴리에스테르 수지, 불포화 폴리에스테르 수지, 아미노 수지, 에폭시 수지, 비닐 수지, 염화 비닐, 염화비닐-비닐 아세테이트 공중합체, 아크릴 수지, 메타크릴 수지, 폴리우레탄 수지, 실리콘 수지, 플루오르 수지, 건성유, 합성건성유, 스티렌-변성 말레산 수지, 폴리아미드 수지, 폴리이미드 수지, 벤조구안아민 수지, 멜라민 수지, 우레아 수지 염화폴리프로필렌, 부티랄 수지 및 염화 비닐리덴 수지를 포함한다.The pigment dispersion composition may further contain a resin. Examples of the thermoplastic resin include petroleum resin, casein, shellac, rosin-modified maleic resin, rosin-modified phenolic resin, nitrocellulose, cellulose acetate butyrate, cyclized rubber, chlorinated rubber, oxidized rubber, A vinyl chloride resin, a vinyl chloride-vinyl acetate copolymer, an acrylic resin, a methacrylic resin, a polyurethane resin, a silicone resin, a fluorine resin, a drying oil, a synthetic drying oil, a polyester resin, an unsaturated polyester resin, an amino resin, , A styrene-modified maleic resin, a polyamide resin, a polyimide resin, a benzoguanamine resin, a melamine resin, a urea resin polypropylene chloride, a butyral resin and a vinylidene chloride resin.
나아가, 감광 수지가 수지로서 사용될 수도 있다. 상기 감광수지로써, 예를 들어, 이소시아네이트기, 알데히드기 또는 에폭시기 또는 신남산 와 같은 반응성 치환체를 갖는 (메트)아크릴 화합물 및 선형 중합체 사이의 반응에 의한 하이드록시기, 카르복시기 또는 아미노기와 같은 반응성 치환체를 갖는 선형 중합체에 (메트)아크릴로일기 또는 스티릴기와 같은 광가교성기를 도입하여 얻어지는 수지; 및 스티렌-말레산 무수물 공중합체 또는 α-올레핀-말레산 무수물 공중합체와 같은 산 무수물을 함유하는 선형 중합체와 하이드록시알킬 (메트)아크릴레이트와 같은 하이드록시기를 갖는 (메트)아크릴 화합물의 반-에스테르화에 의해 얻어지는 수지;가 사용될 수 있다. 이와 같은 수지는 상기 유기 안료 100중량부에 대하여 1 내지 30중량부의 함량으로 사용하는 것이 가능하다. Further, a photosensitive resin may be used as the resin. As the photosensitive resin, for example, a resin having a reactive substituent such as a hydroxyl group, a carboxyl group or an amino group by reaction between a (meth) acrylic compound having a reactive substituent such as an isocyanate group, an aldehyde group or an epoxy group or cinnamic acid, A resin obtained by introducing a photo-crosslinkable group such as a (meth) acryloyl group or a styryl group into a linear polymer; And (meth) acrylic compounds having a hydroxy group such as a hydroxyalkyl (meth) acrylate with a linear polymer containing an acid anhydride such as styrene-maleic anhydride copolymer or? -Olefin-maleic anhydride copolymer, A resin obtained by esterification can be used. Such a resin can be used in an amount of 1 to 30 parts by weight based on 100 parts by weight of the organic pigment.
본 발명의 안료 분산 조성물에 사용되는 유기 용매는 상기 유기 안료 등을 분산시킬 수 있는 것이라면 특별히 한정되지 않으며, 탄소 원자 수 3 내지 12의 에스테르, 케톤, 에테르, 알콜, 탄화수소 등으로부터 선택된 용매가 바람직하다. 상기 에스테르, 케톤, 에테르 또는 알콜은 고리 구조를 가질 수 있다. 에스테르, 케톤 및 에테르와 같은 작용기(-O-, -CO- 및 -COO-)를 2개 이상 갖는 화합물도 용매로서 사용할 수 있으며, 알콜계 히드록시기와 같은 다른 작용기도 동시에 존재할 수 있다. 2개 이상의 작용기를 갖는 용매의 경우, 많은 탄소원자가 상기 작용기를 갖는 화합물에 대하여 정의된 범위 내에 존재할 수 있다.The organic solvent used in the pigment dispersion composition of the present invention is not particularly limited as long as it can disperse the organic pigment and the like, and is preferably a solvent selected from esters, ketones, ethers, alcohols and hydrocarbons having 3 to 12 carbon atoms . The ester, ketone, ether or alcohol may have a ring structure. Compounds having two or more functional groups (-O-, -CO- and -COO-) such as esters, ketones and ethers can also be used as solvents and other functional groups such as alcoholic hydroxyl groups can be present at the same time. In the case of a solvent having two or more functional groups, a large number of carbon atoms may be present within a defined range for the compound having the functional group.
상기 탄소 원자 수 3 내지 12개를 갖는 에스테르로서는 에틸 포르메이트, 프로필 포르메이트, 펜틸 포르메이트, 메틸 아세테이트, 에틸 아세테이트 또는 펜틸 아세테이트를 예로 들 수 있다. 상기 탄소 원자수 3 내지 12개를 갖는 케톤으로서는 아세톤, 메틸 이소부틸 케톤, 메틸 에틸 케톤, 디에틸 케톤, 디이소부틸 케톤, 시클로펜타논, 시클로헥사논 및 메틸시클로헥사논을 예로 들 수 있다. 상기 탄소 원자 수 3 내지 12개를 갖는 에테르로서는 프로필렌 글리콜 모노메틸 에테르 아세테이트, 디이소프로필에테르, 디메톡시메탄, 디메톡시에탄, 1,4-디옥산, 1,3-디옥산, 테트라히드로퓨란, 아니솔 및 펜에톨을 예로 들 수 있다. 또한 2종 이상의 작용기를 갖는 유기 용매로서는 2-에톡시헥실 아세테이트, 2-메톡시에탄올 및 2-부톡시에탄올을 예로 들 수 있다. 또한 상기 염소화 유기 용매와 조합하여 사용가능한 알콜은 선형, 분지형 또는 고리형이 있으며, 이들 중에서 포화지방족 탄화수소가 바람직하다. 상기 알콜의 히드록시기는 1가, 2가 또는 3가가 가능하다. 알콜로서는 메탄올, 에탄올, 1-프로판올, 2-프로판올, 1-부탄올, 2-부탄올, t-부탄올, 1-펜탄올, 2-메틸-2부탄올 및 시클로헥산올을 예로 들 수 있다. 또한 불소화 알콜로서는 2-플루오로에탄올, 2,2,2-트리플루오로에탄올 또는 2,2,3,3-테트라플루오로-1-프로판올을 예로 들 수 있다. 또한 상기 탄화수소는 선형, 분지형 또는 고리형이 가능하며, 방향족 탄화수소 또는 지방족 탄화수소를 사용할 수 있다. 지방족 탄화수소는 포화 또는 불포화 모두 사용할 수 있다. 이와 같은 탄화수소로서는 시클로헥산, 헥산, 벤젠, 에틸벤젠, 톨루엔 및 크실렌을 예로 들 수 있다. Examples of the ester having 3 to 12 carbon atoms include ethyl formate, propyl formate, pentyl formate, methyl acetate, ethyl acetate or pentyl acetate. Examples of the ketone having 3 to 12 carbon atoms include acetone, methyl isobutyl ketone, methyl ethyl ketone, diethyl ketone, diisobutyl ketone, cyclopentanone, cyclohexanone and methylcyclohexanone. Examples of the ether having 3 to 12 carbon atoms include propylene glycol monomethyl ether acetate, diisopropyl ether, dimethoxymethane, dimethoxyethane, 1,4-dioxane, 1,3-dioxane, tetrahydrofuran, Anisole and phenetole are examples. Examples of the organic solvent having two or more functional groups include 2-ethoxyhexyl acetate, 2-methoxyethanol and 2-butoxyethanol. The alcohols usable in combination with the chlorinated organic solvent may be linear, branched or cyclic, of which saturated aliphatic hydrocarbons are preferred. The hydroxy group of the alcohol may be monovalent, divalent or trivalent. Examples of the alcohol include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, t-butanol, 1-pentanol, 2-methyl-2-butanol and cyclohexanol. Examples of the fluorinated alcohols include 2-fluoroethanol, 2,2,2-trifluoroethanol and 2,2,3,3-tetrafluoro-1-propanol. The hydrocarbons may be linear, branched or cyclic, and aromatic hydrocarbons or aliphatic hydrocarbons may be used. Aliphatic hydrocarbons can be used both saturated and unsaturated. Examples of such hydrocarbons include cyclohexane, hexane, benzene, ethylbenzene, toluene and xylene.
이와 같은 유기용매는 상기 안료 분산 조성물에서 상기 유기 안료 입자들을 분산시킬 수 있는 함량으로 사용될 수 있으며, 특별한 제한은 없으나, 상기 유기 안료 100중량부에 대하여 100 내지 1,000중량부의 함량으로 사용할 수 있다. 상기 유기 용매의 함량이 100중량부 미만이면 충분한 안료 분산을 얻을 수가 없고 점도가 높아져 작업성 등이 저하되며, 1,000중량부를 초과하는 경우 안료 농도가 지나치게 낮아 목적하는 색상을 충분히 발현하기 곤란하다는 문제가 있다. The organic solvent may be used in an amount such that the organic pigment particles can be dispersed in the pigment dispersion composition. The organic solvent may be used in an amount of 100 to 1,000 parts by weight based on 100 parts by weight of the organic pigment. If the content of the organic solvent is less than 100 parts by weight, sufficient pigment dispersion can not be obtained, viscosity becomes high and workability is lowered, and when the amount is more than 1,000 parts by weight, the pigment concentration is too low, have.
본 발명의 안료 분산 조성물은 통상의 보조제 또는 첨가제, 예컨대, 계면활성제, 충전제, 표준화제, 소포제, 항분진제, 증진제, 정전기 방지제, 보존제, 건조 지연제, 습윤화제, 항산화제 등을 바람직하게는 안료 분산 조성물 총 중량을 기준으로 0.01 내지 10중량%, 특히 0.5 내지 5중량%의 양으로 추가로 포함할 수 있다.The pigment dispersion composition of the present invention may contain conventional auxiliary agents or additives such as surfactants, fillers, standardizers, antifoaming agents, anti-dust agents, enhancing agents, antistatic agents, preservatives, drying retarders, wetting agents, antioxidants, In an amount of 0.01 to 10% by weight, especially 0.5 to 5% by weight, based on the total weight of the pigment dispersion composition.
한편, 안료 분산 조성물을 제조하기 위해서는, 유기 안료는, 1차 입자 지름이 100㎚ 이하이거나, 미립화 처리에 의해 1차 입자 지름을 100㎚ 이하로 한 유기안료를 이용하는 것이, 얻어지는 안료 분산 조성물의 투명성이나 선명성의 향상이라는 관점으로부터 바람직하다. 유기 안료의 미립화 처리법으로서는, 예를 들면, 식염(common salt)의 존재 하에서 밀링을 실시하는 솔트 밀링법(salt-milling method) 등(예를 들면, 일본 특개 2001-220520 공보 및 일본 특개 2001-264528 공보)을 들 수 있지만, 이들에 한정되지 않는다.On the other hand, in order to prepare the pigment dispersion composition, it is preferable that the organic pigment has a primary particle diameter of 100 nm or less, or an organic pigment having a primary particle diameter of 100 nm or less by the atomization treatment, And from the viewpoint of improvement of sharpness. Examples of the atomization treatment method of the organic pigment include a salt-milling method in which milling is carried out in the presence of a common salt (see, for example, JP-A-2001-220520 and JP-A-2001-264528 ), But the present invention is not limited thereto.
본 발명의 일실시 예에 따른 안료 분산 조성물은 각각 상기 유기 안료와 상기 안료 첨가제를 종래 공지의 방법(예를 들면, 일본 특개 2001-271004 공보 및 특개 2004-91497 공보)에 의해 혼합하여 제조할 수 있다. 예를 들면, 상기 유기 안료와 상기 안료 첨가제의 분말끼리 혼합하는 방법, 물이나 용해력이 있는 유기용매에 분산시킨 상기 유기 안료와 상기 안료 첨가제와의 서스펜션끼리 혼합하는 방법, 유기 안료의 제조 공정 중의 임의의 공정에 상기 안료 첨가제를 첨가하는 방법 등을 들 수 있지만, 제조 방법은 특별히 한정되지 않는다. 상기 유기 안료 제조 공정중의 임의의 공정으로서는, 예를 들면, 솔트 밀링(salt milling)을 들 수 있지만, 이것에 한정되지 않는다. 상기 안료 첨가제를 첨가할 때 상태로서는, 분말, 페이스트, 서스펜션의 형태를 들 수 있지만, 이에 한정되지 않는다. The pigment dispersion composition according to one embodiment of the present invention can be produced by mixing the organic pigment and the pigment additive respectively by a conventionally known method (for example, Japanese Patent Application Laid-Open Nos. 2001-271004 and 2004-91497) have. For example, a method of mixing the organic pigment and the pigment additive powder, a method of mixing suspensions between the organic pigment and the pigment additive dispersed in water or a dissolvable organic solvent, And a method of adding the pigment additive to the process of the present invention. However, the production method is not particularly limited. Examples of the optional step in the organic pigment production process include, but are not limited to, salt milling. The state when the pigment additive is added may be in the form of powders, pastes or suspensions, but is not limited thereto.
일례로서, 본 발명의 안료 분산 조성물은 상기 각 성분을 적정량 투입한 후 교반기로 혼합하면서 유기 안료 파우더를 습윤(wetting)시키는 습윤 분산 안정화 공정을 통해 제조될 수 있으며, 이렇게 제조된 조성물 내 유기 안료는 20 내지 150 nm의 평균입자 크기를 갖게 된다. 이때, 안료 분산의 효율성을 고려하여, 물리적 충돌력을 극대화시키기 위해 0.05 내지 2.0mm 지름의 비드(beads)를 사용할 수 있으며, 이러한 비드는 글라스, 스테인레스 스틸 또는 지르코늄 등의 재질인 것일 수 있다. For example, the pigment dispersion composition of the present invention can be prepared by a wet dispersion stabilization process in which an organic pigment powder is wetted while mixing the components with an appropriate amount of the above components, and the organic pigment in the thus- And have an average particle size of 20 to 150 nm. In order to maximize the physical impact force in consideration of the efficiency of pigment dispersion, beads having a diameter of 0.05 to 2.0 mm may be used. Such beads may be glass, stainless steel, zirconium or the like.
또한, 상기 교반 공정 시 사용되는 분산기로는 비드밀, 롤밀, 아트라이터, 수퍼밀, 디졸버, 호모믹서, 샌드밀, 3-롤밀, 디스크밀, 페인트세이커 및 스칸덱스 등이 있으며, 일반적으로 비드밀이 가장 많이 사용된다. Examples of the dispersing machine used in the stirring step include a bead mill, a roll mill, an attritor, a super mill, a dissolver, a homomixer, a sand mill, a 3-roll mill, a disc mill, a paint shaker and a scandel. Bead mill is the most used.
또한 본 발명은 본 발명의 안료 분산 조성물을 포함하는 컬러 레지스트 조성물을 제공한다. The present invention also provides a color resist composition comprising the pigment dispersion composition of the present invention.
또한 본 발명은 본 발명의 컬러 레지스트 조성물을 이용하여 제조되는 컬러필터를 제공한다.The present invention also provides a color filter manufactured using the color resist composition of the present invention.
상세하게 본 발명의 안료 분산 조성물은 도료, 인쇄잉크 등으로서도 이용할 수 있으며, 감광성 피막 형성 재료와 혼합하여 광조사에 의해 화상형성이 가능한 컬러 레지스트 조성물로서도 적용될 수 있다. 본 발명의 안료 분산 조성물이 포함된 컬러 레지스트 조성물을 이용하여 공지의 방법 및 구조로 화소를 형성하게 되면 우수한 특성의 컬러필터를 얻게 된다. 컬러 레지스트 조성물은 본 발명의 안료 분산 조성물과, 감광성 피막 형성 재료를 혼합하여 고 분산이 되어 얻어진다. 감광성 피막 형성 재료는 특별히 제한되지 않는다. 일반적으로 감광성 폴리아크릴레이트계 수지, 감광성 아크릴계 수지, 감광성 폴리아미드계 수지, 감광성 폴리이미드계 수지, 혹은 감광성 불포화 폴리에스테르계 수지 등의 감광성 수지 바니스, 또는 그러한 수지 반응 희석제로서 모노머 또는 올리고머가 더 첨가된 바니스, 광개시제(필요에 따라서 증감제와 함께), 용제 등의 성분으로 이루어진다. 본 발명의 안료 분산 조성물을 이용함으로써, 분산성, 분산 안정성, 투명성 및 선명성이 뛰어난 컬러필터 화소 형성용 컬러 레지스트 조성물 및 컬러필터를 얻을 수 있다. In detail, the pigment dispersion composition of the present invention can be used as a coating material, a printing ink, or the like, and can be applied as a color resist composition which can be mixed with a photosensitive film forming material and form an image by light irradiation. When a pixel is formed by a known method and structure using a color resist composition including the pigment dispersion composition of the present invention, a color filter having excellent characteristics is obtained. The color resist composition is obtained by mixing the pigment-dispersed composition of the present invention and the photosensitive film-forming material in a highly dispersed state. The photosensitive film-forming material is not particularly limited. In general, a photosensitive resin varnish such as a photosensitive polyacrylate resin, a photosensitive acrylic resin, a photosensitive polyamide resin, a photosensitive polyimide resin or a photosensitive unsaturated polyester resin, or a monomer or oligomer is further added as such a resin reaction diluent A varnish, a photoinitiator (if necessary, together with a sensitizer), and a solvent. By using the pigment dispersion composition of the present invention, it is possible to obtain a color resist composition and a color filter for color filter pixel formation which are excellent in dispersibility, dispersion stability, transparency and clarity.
상기 모노머 또는 올리고머로서는, 예를 들면, (메타)아크릴산에스테르, (메타)아크릴산, (메타)아크릴아미드, 초산비닐, 스티렌, (메타)크릴로니트릴, (메타)아크릴레이트 올리고머 등을 들 수 있지만, 이들에 한정되지 않는다. 상기 광개시제로서는, 예를 들면, 아세트페논계, 벤조인계, 벤조페논계, 티옥산톤계, 트리아진계, 카르바졸계, 이미다졸계 등을 들 수 있지만, 이들에 한정되지 않는다. 상기 증감제로서는, 예를 들면, 아실포스핀옥사이드 (acylphosphine oxide), 메틸페닐글리옥실레이트 (methylphen ylglyoxylate), 퀴논계(quinone-based), 안트라퀴논계(anthraquinone-based), 이소프탈로페논계(isophthalo phenone-based), 에스테르계(ester-based), 벤질계(benzil-based), 벤조페논계 (benzophenone-based) 등을 들 수 있지만, 이들에 한정되지 않는다. 용제로서는, 예를 들면, (폴리)알킬렌글리콜모노알킬에테르, (폴리)알킬렌글리콜모노알킬 에테르아세테이트, 에테르, 케톤, 유산알킬에스테르, 그 외의 에스테르, 방향족 탄화수소, 아미드 등을 들 수 있지만, 이들에 한정되지 않는다. Examples of the monomer or oligomer include (meth) acrylic acid ester, (meth) acrylic acid, (meth) acrylamide, vinyl acetate, styrene, (meth) acrylonitrile, , But are not limited thereto. Examples of the photoinitiator include, but are not limited to, acetophenone, benzoin, benzophenone, thioxanthone, triazine, carbazole, and imidazole. Examples of the sensitizer include acylphosphine oxide, methylphen ylglyoxylate, quinone-based, anthraquinone-based, isophthaloyl-isophthaloquinone, phenone-based, ester-based, benzyl-based, benzophenone-based, and the like. Examples of the solvent include (poly) alkylene glycol monoalkyl ether, (poly) alkylene glycol monoalkyl ether acetate, ether, ketone, fatty acid alkyl ester, other esters, aromatic hydrocarbons and amides. But are not limited thereto.
본 발명의 안료 첨가제는 휘도와 명암비가 높아 이를 포함하는 안료 분산 조성물의 광학적 특성을 향상시킨다.The pigment additive of the present invention has high brightness and contrast ratio and thus improves the optical properties of the pigment dispersion composition containing it.
본 발명의 안료 첨가제는 안료 분산 조성물에 포함되어 미세한 유기 안료의 응집을 억제해 안료 분산 조성물의 분산성과 더불어 분산 안정성을 높인다.The pigment additive of the present invention is contained in a pigment dispersion composition to inhibit the aggregation of fine organic pigments, thereby enhancing dispersion stability of the pigment dispersion composition as well as dispersion stability.
본 발명의 안료 분산 조성물은 상술한 바와 같이 본 발명의 신규한 안료 첨가제를 포함하여 광학적 특성뿐만 아니라 분산성과 분산 안정성이 매우 높다.As described above, the pigment dispersion composition of the present invention includes the novel pigment additive of the present invention and has very high dispersibility and dispersion stability as well as optical properties.
본 발명의 컬러 레지스트 조성물 또한 분산성과 분산 안정성이 높은 본 발명의 안료 분산 조성물을 포함함으로써 양질의 컬러 필터를 제조할 수 있다. The color resist composition of the present invention also includes a pigment dispersion composition of the present invention having high dispersibility and high dispersion stability, so that a color filter of good quality can be produced.
이하 구체적인 실시 예를 통해 안료 첨가제의 구체예 및 합성 방법 등을 설명한다. 하기 설명은 본 발명의 일례이므로 나열된 구조나 설명으로 한정되지 않는다.Hereinafter, concrete examples of the pigment additive, a synthesis method and the like will be described through specific examples. The following description is only an example of the present invention, and thus the present invention is not limited to the structure or the description.
[실시예 1] 안료 첨가제 A의 제조[Example 1] Production of Pigment Additive A
중간체(2,6-bis(mesitylamino)-4-methylpyridine-3-carbonitrile)의 합성Synthesis of intermediate (2,6-bis (mesitylamino) -4-methylpyridine-3-carbonitrile)
2,4,6-trimethyaniline 9.0ml(64.16 mmol) 및 NMP 0.8ml에, 2,6-dichloro-4-methylnicotinon itrile 3g(16,04 mmol)과 zinc oxide 1530mg을 첨가하고, oil bath를 180℃로 승온했다. 반응 중에 생성되는 물을 제거하면서 180℃에 4시간 가열 교반시켰다. 그 뒤, 80℃까지 냉각하고, 물 1000ml에 반응액을 30분에 걸쳐 적하한 후 실온까지 냉각 후 여과했다. 얻어진 결정을 세척, 건조하고 목적의 화합물을 4.2g(수율 68%) 얻었다. (16.04 mmol) of 2,6-dichloro-4-methylnicotinon itrile and 1530 mg of zinc oxide were added to 9.0 ml (64.16 mmol) of 2,4,6-trimethyaniline and 0.8 ml of NMP, It has warmed up. And the mixture was heated and stirred at 180 캜 for 4 hours while removing water produced during the reaction. Thereafter, the solution was cooled to 80 DEG C, and the reaction solution was added dropwise to 1000 ml of water over 30 minutes, cooled to room temperature, and then filtered. The obtained crystals were washed and dried to obtain 4.2 g (yield: 68%) of the aimed compound.
안료 첨가제 A의 제조Preparation of pigment additive A
별도로, 2,6-bis(mesitylamino)-4-methylnicotinonitrile 2.1g (5.5 mmol)을 3목 플라스크에 넣고 sodium acetate 5.9g (72.59 mmol), 5ml 의 DMF와 5ml의 EA를 첨가하였다. 혼합물을 교반시키고 5℃의 내부 온도로 냉각시켰다. 여기에 디아조늄 염을 10분에 걸쳐 첨가하고, 추가로 1시간 동안 교반을 계속시켰다. 50ml의 포화 염화나트륨 수용액을 반응 혼합물에 첨가하였다. 이와 같이 형성된 침전물을 흡입에 의한 여과에 의해 수집하여 안료 첨가제 A, 2.5g (수율 75%)를 얻었다. Separately, 2.1 g (5.5 mmol) of 2,6-bis (mesitylamino) -4-methylnicotinonitrile was added to a three-necked flask and 5.9 g (72.59 mmol) of sodium acetate, 5 ml of DMF and 5 ml of EA were added. The mixture was stirred and cooled to an internal temperature of 5 < 0 > C. The diazonium salt was added thereto over 10 minutes, and stirring was continued for an additional 1 hour. 50 ml of a saturated aqueous sodium chloride solution was added to the reaction mixture. The precipitate thus formed was collected by filtration by suction to obtain 2.5g (yield 75%) of pigment additive A.
ESI-MS : MW 1179.33, m/z 1178.40
ESI-MS: MW 1179.33, m / z 1178.40
[실시예 2] 안료 첨가제 B의 제조[Example 2] Production of Pigment Additive B
중간체의 제조Preparation of intermediate
2,6-diethylaniline 13.2ml(80.2 mmol) 및 NMP 0.8ml에, 2,6-dichloro-4-methylnicotinonitrile 3g(16,04 mmol)과 zinc oxide 1530mg을 첨가하고, oil bath에 180℃로 승온했다. 반응 중에 생성되는 물을 제거하면서 180℃에세 4시간동안 가열 교반시켰다. 이후, 80℃까지 냉각시키고, 반응혼합액에 물 1000ml을 30분에 걸쳐 적하하고 실온까지 냉각 후 여과했다. 얻어진 결정을 세척, 건조하고 목적의 화합물을 4.0g(수율 60%) 얻었다.
(16.04 mmol) of 2,6-dichloro-4-methylnicotinonitrile and 1530 mg of zinc oxide were added to 13.2 ml (80.2 mmol) of 2,6-diethylaniline and 0.8 ml of NMP, and the temperature was raised to 180 ° C in an oil bath. The resulting mixture was heated and stirred at 180 캜 for 4 hours while removing water produced during the reaction. Thereafter, the reaction mixture was cooled to 80 deg. C, 1000 ml of water was added dropwise to the reaction mixture over 30 minutes, cooled to room temperature and filtered. The obtained crystals were washed and dried to obtain 4.0 g (yield: 60%) of the aimed compound.
안료 첨가제 B의 제조Preparation of pigment additive B
2,2'-Benzidinedisulfonic acid 1g (2.9 mmol), 1ml의 진한 염산, 및 3ml의 물의 혼합물을 5℃의 내부 온도에서 교반하고, 0.4g (5.8 mmol)의 Sodium nitrite를 분획하여 5분에 걸쳐 첨가하였다, 첨가 후 30분 동안 교반을 계속 하여 디아조늄 염을 형성하였다. A mixture of 1 g (2.9 mmol) of 2,2'-benzidinedisulfonic acid, 1 ml of concentrated hydrochloric acid and 3 ml of water was stirred at an internal temperature of 5 ° C and 0.4 g (5.8 mmol) of sodium nitrite was added and added over 5 minutes The stirring was continued for 30 minutes after the addition to form a diazonium salt.
별도로, 2,6-bis((2,6-diethylphenyl)amino)-4-methylnicotinonitrile 2.2g (5.5 mmol)을 3목 플라스크에 넣고 sodium acetate 5.9g (72.59 mmol), 5ml 의 DMF와 5ml의 EA를 첨가하였다. 혼합물을 교반하고 내부 온도로 5℃가 되도록 냉각시켰다. 반응 혼합물에 디아조늄 염을 10분에 걸쳐 첨가하고 추가로 1시간 동안 교반을 계속하였다. 50ml의 포화 염화나트륨 수용액을 반응 혼합물에 첨가하여 형성된 침전물을 흡입에 의한 여과에 의해 수집하여 안료 첨가제 B, 2.4g (수율 69%)를 얻었다. Separately, 2.2 g (5.5 mmol) of 2,6-bis ((2,6-diethylphenyl) amino) -4-methylnicotinonitrile was added to a three-necked flask and 5.9 g (72.59 mmol) of sodium acetate, 5 ml of DMF and 5 ml of EA . The mixture was stirred and cooled to an internal temperature of 5 < 0 > C. The diazonium salt was added to the reaction mixture over 10 minutes and stirring was continued for an additional 1 hour. 50 ml of a saturated aqueous sodium chloride solution was added to the reaction mixture and the precipitate formed was collected by filtration by suction to obtain 2.4 g (69% yield) of pigment additive B.
ESI-MS : MW 1235.43, m/z 1234.46
ESI-MS: MW 1235.43, m / z 1234.46
[실시예 3] 안료 첨가제 C의 제조[Example 3] Production of Pigment Additive C
중간체의 제조Preparation of intermediate
2-ethylhexan-1-amine 11.4ml(80.2 mmol) 및 NMP 0.8ml에 2,6-dichloro-4-methyl nicotinonitrile 3g(16,04 mmol)과 zinc oxide 1530mg을 첨간 가열하고, oil bath를 180℃로 승온했다. 반응 중에 생성되는 물을 제거하면서 180℃에 4시간동안 교반시켰다. 그 뒤, 80℃까지 냉각하고, 반응혼합액에 물 1000ml를 30분 걸쳐 적하하고, 실온까지 냉각 후 여과했다. 얻어진 결정을 세척, 건조하고 목적의 화합물을 4.1g(수율 62%) 얻었다. (16.04 mmol) of 2,6-dichloro-4-methyl nicotinonitrile and 1530 mg of zinc oxide were added to 11.4 ml (80.2 mmol) of 2-ethylhexan-1-amine and 0.8 ml of NMP, It has warmed up. And the mixture was stirred at 180 캜 for 4 hours while removing water produced during the reaction. Thereafter, the reaction mixture was cooled to 80 deg. C, and 1000 ml of water was added dropwise to the reaction mixture over 30 minutes, cooled to room temperature, and then filtered. The obtained crystals were washed and dried to obtain 4.1 g (yield: 62%) of the aimed compound.
안료 첨가제 C의 제조Preparation of pigment additive C
별도로, 2,6-bis(hexylamino)-4-methylnicotinonitrile 2.0g (5.5 mmol)을 3목 플라스크에 놓고 sodium acetate 5.9g (72.59 mmol), 5ml 의 DMF와 5ml의 EA를 첨가하여 교반하고 5℃의 내부 온도로 냉각시켰다. 여기에 상기에서 제조한 디아조늄 염을 10분에 걸쳐 첨가하고, 추가로 1시간 동안 교반을 계속하였다. 50ml의 포화 염화나트륨 수용액을 반응 혼합물에 첨가하여 형성된 침전물을 흡입에 의한 여과에 의해 수집하여 2.4g (수율 72%)를 얻었다. Separately, 2.0 g (5.5 mmol) of 2,6-bis (hexylamino) -4-methylnicotinonitrile was placed in a three-necked flask, 5.9 g (72.59 mmol) of sodium acetate, 5 ml of DMF and 5 ml of EA were added, And cooled to an internal temperature. The diazonium salt prepared above was added thereto over 10 minutes, and stirring was further continued for 1 hour. 50 ml of a saturated aqueous sodium chloride solution was added to the reaction mixture, and the formed precipitate was collected by filtration by suction to obtain 2.4 g (yield 72%).
ESI-MS : MW 1155.47, m/z 1154.59
ESI-MS: MW 1155.47, m / z 1154.59
[실시예 4] 안료 첨가제 D의 합성[Example 4] Synthesis of pigment additive D
별도로, 4-(3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonic acid 1.4g (5.5 mmol)을 3목 플라스크에 놓고 sodium acetate 5.9g (72.59 mmol), 5ml 의 DMF와 5ml의 EA를 첨가하여 교반하고 내부온도가 5℃가 되도록 냉각시켰다. 여기에 상기에서 제조한 디아조늄 염을 10분에 걸쳐 첨가하고, 추가로 1시간 동안 교반을 계속하였다. 50ml의 포화 염화나트륨 수용액을 반응 혼합물에 첨가하여 형성된 침전물을 흡입에 의한 여과에 의해 수집하여 안료 첨가제 D, 1.7g (수율 67%)를 얻었다. Separately, 1.4 g (5.5 mmol) of 4- (3-methyl-5-oxo-4,5-dihydro-1H- pyrazol-1-yl) benzenesulfonic acid was placed in a three- 5 ml of DMF and 5 ml of EA were added and stirred and cooled to an internal temperature of 5 캜. The diazonium salt prepared above was added thereto over 10 minutes, and stirring was further continued for 1 hour. 50 ml of a saturated sodium chloride aqueous solution was added to the reaction mixture, and the precipitate formed was collected by filtration by suction to obtain 1.7 g (67% yield) of pigment additive D.
ESI-MS : MW 918.82, m/z 918.01
ESI-MS: MW 918.82, m / z 918.01
[실시예 5] 안료 첨가제 E의 합성[Example 5] Synthesis of pigment additive E
별도로, 5-oxo-1-(4-sulfophenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid 1.4g (5.5 mmol)을 3목 플라스크에 놓고 sodium acetate 5.9g (72.59 mmol), 5ml 의 DMF와 5ml의 EA를 첨가하여 교반하고 5℃의 내부 온도로 냉각시켰다. 여기에 상기 제조한 디아조늄 염을 10분에 걸쳐 첨가하고, 추가로 1시간 동안 교반을 계속하였다. 50ml의 포화 염화나트륨 수용액을 반응 혼합물에 첨가하여 형성된 침전물을 흡입에 의한 여과에 의해 수집하여 안료 첨가제 E, 1.9g (수율 70%)를 얻었다. Separately, 1.4 g (5.5 mmol) of 5-oxo-1- (4-sulfophenyl) -4,5-dihydro-1H-pyrazole-3-carboxylic acid was placed in a three-necked flask and 5.9 g (72.59 mmol) Of DMF and 5 ml of EA were added and stirred and cooled to an internal temperature of 5 < 0 > C. The diazonium salt prepared above was added over 10 minutes and stirring was continued for a further 1 hour. 50 ml of saturated sodium chloride aqueous solution was added to the reaction mixture, and the precipitate formed was collected by filtration by suction to obtain 1.9 g (70% yield) of pigment additive E.
ESI-MS : MW 978.78, m/z 977.96
ESI-MS: MW 978.78, m / z 977.96
[실시예 6] 안료 첨가제 F의 제조[Example 6] Production of pigment additive F
2,2'-Benzidinedisulfonic acid 1g (2.9 mmol), 1ml의 진한 염산, 및 3ml의 물의 혼합물을 5℃의 내부 온도에서 교반하고, 0.4g (5.8 mmol)의 Sodium nitrite를 분획하여 5분에 걸쳐 첨가하였다, 첨가 후 30분 동안 교반을 계속 하여 디아조늄 염을 형성하였다.A mixture of 1 g (2.9 mmol) of 2,2'-benzidinedisulfonic acid, 1 ml of concentrated hydrochloric acid and 3 ml of water was stirred at an internal temperature of 5 ° C and 0.4 g (5.8 mmol) of sodium nitrite was added and added over 5 minutes The stirring was continued for 30 minutes after the addition to form a diazonium salt.
별도로, 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one 0.9g (5.5 mmol)을 3목 플라스크에 놓고 sodium acetate 5.9g (72.59 mmol), 5ml 의 DMF와 5ml의 EA를 첨가하였다. 혼합물을 교반하고 내부 온도가 5℃가 되도록 냉각시켰다. 여기에 상기에서 제조한 디아조늄 염을 10분에 걸쳐 첨가하고, 추가로 1시간 동안 교반을 계속하였다. 50ml의 포화 염화나트륨 수용액을 반응 혼합물에 첨가하여 형성된 침전물을 흡입에 의한 여과에 의해 수집하여 안료 첨가제 F, 1.4g (수율 67%)를 얻었다. Separately, 0.9 g (5.5 mmol) of 3-methyl-1-phenyl-1H-pyrazol-5 (4H) -one was placed in a three-necked flask and 5.9 g (72.59 mmol) of sodium acetate, 5 ml of DMF and 5 ml of EA Respectively. The mixture was stirred and cooled to an internal temperature of 5 < 0 > C. The diazonium salt prepared above was added thereto over 10 minutes, and stirring was further continued for 1 hour. 50 ml of a saturated aqueous sodium chloride solution was added to the reaction mixture, and the precipitate formed was collected by filtration by suction to obtain 1.4 g of pigment additive F (67% yield).
ESI-MS : MW 758.69, m/z 758.109
ESI-MS: MW 758.69, m / z 758.109
[실시예 7 내지 12 및 비교예 1] 안료 분산 조성물의 제조[Examples 7 to 12 and Comparative Example 1] Preparation of pigment dispersion composition
하기 표 1과 같은 조성비로 안료, 안료 첨가제를 혼합하여 0.5mm 지르코니아 100g을 넣고 페인트 쉐이커(paint shaker)에서 5시간 동안 분산 후 안료 분산 조성물을 얻었다. The pigment and the pigment additive were mixed at the composition ratios shown in Table 1 below, and 100 g of 0.5 mm zirconia was added and dispersed in a paint shaker for 5 hours to obtain a pigment dispersion composition.
제조된 실시 예 6 내지 12 및 비교 예 1의 안료 분산 조성물로 형성된 패턴을 이용하여 각각의 조성물에 대한 평가를 하기에 기재된 바와 같이 실시하였다.The evaluation of each composition was carried out as described below using the patterns formed from the pigment dispersion compositions of Examples 6 to 12 and Comparative Example 1 thus prepared.
평가의 결과는 하기 표 2에 나타내었다.The results of the evaluation are shown in Table 2 below.
하기에 평가 방법이나 기준으로 특별히 기재되지 않은 사항은 본 기술 분야에서 통상적으로 사용되는 평가규격 또는 통상의 방법에 따른다.Items not specifically described in the following evaluation method or standard are in accordance with the evaluation standard or ordinary method commonly used in this technical field.
(1) 콘트라스트(1) Contrast
상기 실시 예 6 내지 12, 비교 예 1의 안료 분산 조성물을 판두께 0.5mm의 60mm X 60mm 사이즈(Size)의 유리 기판에 경화 후의 x=0.650이 (C광원)이 되도록 스핀 코팅하고, 90℃로 100초 건조한 뒤 초고압 수은 램프를 이용, 적산광량 60mJ/cm2 자외선 노광을 행했으며 도포 유리 기판을 230℃ 90분 가열한 후 각 건조 코팅 필름에 대하여 휘도계 CT-1(쓰보사카) 및 편광 플래이트를 사용하여 평행인 경우의 휘도와 직교인 경우의 휘도의 비율로써 콘트라스트 값을 계산하였다.
The pigment-dispersed compositions of Examples 6 to 12 and Comparative Example 1 were spin-coated on a glass substrate of 60 mm X 60 mm size having a plate thickness of 0.5 mm so that x = 0.650 after curing (C light source) 100 seconds dry after ultra-high pressure mercury lamp used, the accumulated light quantity 60mJ / cm 2 ultraviolet ray was carried out exposing the coated glass substrate 230 ℃ after heating 90 minutes the luminance meter CT-1 (sseubo saccharose) and the polarizing plates on each dry coating film The contrast value was calculated as the ratio of the luminance in the case of parallelism to the luminance in the case of orthogonalization.
(2) 휘도(2) Brightness
휘도 측정기로서 색 휘도 측정기 MCPD 3000(오츠카사)을 사용하여 x=0.650 (C광원)에서의 RY를 측정하였다. Display 상에서 RGB 각각 성분의 x, y 좌표는 한 점으로 표시되며 여기서 말한 x는 Chromaticity diagram에서 레드 성분의 크기를, RY는 레드 성분의 명도를 나타낸다(y는 그린 성분의 크기, GY는 그린 성분의 명도, z는 블루 성분의 크기, BY는 블루 성분의 명도를 나타낸다). As a luminance meter, RY was measured at x = 0.650 (C light source) using a color luminance meter MCPD 3000 (Otsuka). The x and y coordinates of each component of RGB on the display are represented by a point, where x is the size of the red component in the chromaticity diagram and RY is the brightness of the red component (y is the size of the green component, GY is the size of the green component Brightness, z is the size of the blue component, and BY is the brightness of the blue component).
상기 표 2 에서와 같이, 본 발명의 실시 예에 따른 안료 분산 조성물은 비교 예에 대비하여 점도가 낮으며 시간에 따른 점도변화가 미미하여 분산 안정성이 우수한 것을 알 수 있으며 콘트라스트와 휘도가 매우 우수한 것을 알 수 있다. As shown in Table 2, the pigment dispersion composition according to the present invention has low viscosity as compared with the comparative example and shows little dispersion of viscosity with time, showing excellent dispersion stability. .
Claims (11)
[화학식 1]
[상기 화학식 1에서,
A는
R1은 수소, (C1-C30)알킬, (C3-C30)시클로알킬, (C3-C30)헤테로시클로알킬, (C1-C30)알콕시, (C6-C30)아릴, (C6-C30)아르(C1-C30)알킬, (C3-C30)헤테로아릴, (C6-C30)아릴옥시, (C1-C30)알킬옥시, 모노(C1-C30)알킬아미노, 디(C1-C30)알킬아미노, 모노(C6-C30)아릴아미노, 디(C6-C30)아릴아미노, (C1-C30)알킬카보닐, 카르복실산기, 술포닐, 할로겐, 아미노, 시아노 또는 니트로이며,
o는 1 내지 3의 정수이며,
p는 1 내지 2의 정수이며;
M은 Na, H, K 또는 Li이며;
B는 수소, 아미노, (C1-C30)알킬, (C1-C30)알콕시, (C6-C30)아릴, 모노(C1-C30)알킬아미노, 디(C1-C30)알킬아미노, 모노(C6-C30)아릴아미노 또는 디(C6-C30)아릴아미노이며;
상기 R1의 알킬, 시클로알킬, 헤테로시클로알킬, 알콕시, 아릴, 아르알킬, 헤테로아릴, 아릴옥시, 알킬옥시, 모노알킬아미노, 디알킬아미노, 모노아릴아미노, 디아릴아미노 및 알킬카보닐과 B의 알킬, 알콕시, 아릴, 모노알킬아미노, 디알킬아미노, 모노아릴아미노 및 디아릴아미노는 할로겐, 카르복실산기, 술포닐, 시아노, 니트로, 히드록시, (C1-C30)알킬, (C6-C30)아릴, (C3-C30)헤테로아릴에서 선택되는 어느 하나이상으로 더 치환될 수 있다.]A pigment additive represented by the following formula (1):
[Chemical Formula 1]
[In the above formula (1)
A is
R 1 is hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, (C3-C30) heterocycloalkyl, (C1-C30) alkoxy, (C6-C30) aryl, (C6-C30) ar ( (C1-C30) alkyl, (C3-C30) heteroaryl, (C6-C30) aryloxy, (C6-C30) arylamino, di (C6-C30) arylamino, (C1-C30) alkylcarbonyl, carboxylic acid group, sulfonyl, halogen, amino, cyano or nitro,
o is an integer from 1 to 3,
p is an integer of 1 to 2;
M is Na, H, K, or Li;
B is selected from the group consisting of hydrogen, amino, (C 1 -C 30) alkyl, (C 1 -C 30) alkoxy, (C 6 -C 30) aryl, mono (C 1 -C 30) alkylamino, ) Arylamino or di (C6-C30) arylamino;
Wherein R 1 is selected from the group consisting of alkyl, cycloalkyl, heterocycloalkyl, alkoxy, aryl, aralkyl, heteroaryl, aryloxy, alkyloxy, monoalkylamino, dialkylamino, monoarylamino, diarylamino and alkylcarbonyl and B (C1-C30) alkyl, (C6-C30) alkyl, alkoxy, aryl, monoalkylamino, dialkylamino, monoarylamino, and diarylamino groups are optionally substituted with one or more substituents selected from the group consisting of halogen, carboxylic acid group, sulfonyl, cyano, nitro, C30) aryl, (C3-C30) heteroaryl, and the like.
상기 화학식 1에서 R1은 서로 독립적으로 (C1-C30)알킬, (C6-C30)아릴, (C6-C30)아르(C1-C30)알킬, 모노(C1-C30)알킬아미노, 디(C1-C30)알킬아미노, 모노(C6-C30)아릴아미노, 디(C6-C30)아릴아미노, (C1-C30)알킬카보닐, 카르복실산기, 술포닐, 할로겐, 시아노, 아미노 또는 니트로이며;
상기 R1의 알킬, 아릴, 아르알킬, 모노알킬아미노, 디알킬아미노, 모노아릴아미노 및 디아릴아미노는 할로겐, 카르복실산기, 술포닐, 시아노, 니트로, 히드록시, (C1-C30)알킬, (C6-C30)아릴, (C3-C30)헤테로아릴에서 선택되는 어느 하나이상으로 더 치환될 수 있는 것인 안료 첨가제.The method according to claim 1,
Wherein R 1 is independently selected from the group consisting of (C 1 -C 30) alkyl, (C 6 -C 30) aryl, (C 6 -C 30) aryl (C 1 -C 30) alkyl, C30) alkylamino, mono (C6-C30) arylamino, di (C6-C30) arylamino, (C1-C30) alkylcarbonyl, carboxylic acid group, sulfonyl, halogen, cyano, amino or nitro;
Wherein said alkyl, aryl, aralkyl, monoalkylamino, dialkylamino, monoarylamino and diarylamino of said R 1 are independently selected from the group consisting of halogen, carboxylic acid group, sulfonyl, cyano, nitro, hydroxy, (C 1 -C 30) , (C6-C30) aryl, and (C3-C30) heteroaryl.
상기 화학식 1은 하기 화학식 2로 표시되는 안료 첨가제.
[화학식 2]
[상기 화학식 2에서,
R11 내지 R12는 서로 독립적으로 수소, (C1-C30)알킬, (C6-C30)아릴, 또는 (C6-C30)아르(C1-C30)알킬이며;
R13는 서로 독립적으로 수소, (C1-C30)알킬 또는 카르복실산기이며;
상기 R11 내지 R12의 알킬, 아릴 및 아르알킬과 R13의 알킬은 할로겐, 카르복실산기, 술포닐, 시아노, 니트로, 히드록시, (C1-C30)알킬, (C6-C30)아릴, (C3-C30)헤테로아릴에서 선택되는 어느 하나이상으로 더 치환될 수 있다.The method according to claim 1,
Wherein the formula (1) is represented by the following formula (2).
(2)
[In the formula (2)
R 11 to R 12 are independently of each other hydrogen, (C 1 -C 30) alkyl, (C 6 -C 30) aryl or (C 6 -C 30) aryl (C 1 -C 30) alkyl;
R 13 is independently from each other hydrogen, (C 1 -C 30) alkyl or a carboxylic acid group;
The alkyl, aryl and aralkyl of R 11 to R 12 and the alkyl of R 13 are independently selected from the group consisting of halogen, carboxylic acid group, sulfonyl, cyano, nitro, hydroxy, (C 1 -C 30) alkyl, (C 6 -C 30) (C3-C30) heteroaryl. ≪ / RTI >
상기 화학식 1은 하기 화합물에서 선택되는 것인 안료 첨가제.
Wherein the formula (1) is selected from the following compounds.
하기 화학식 4의 디아조늄염과 하기 화학식 5를 반응시켜 하기 화학식 1로 표시되는 안료 첨가제를 제조하는 단계;를 포함하는 안료 첨가제의 제조방법.
[화학식 1]
[화학식 4]
[화학식 5]
[상기 화학식 1 및 화학식 4 내지 5에서,
A는
R1은 수소, (C1-C30)알킬, (C3-C30)시클로알킬, (C3-C30)헤테로시클로알킬, (C1-C30)알콕시, (C6-C30)아릴, (C6-C30)아르(C1-C30)알킬, (C3-C30)헤테로아릴, (C6-C30)아릴옥시, (C1-C30)알킬옥시, 모노(C1-C30)알킬아미노, 디(C1-C30)알킬아미노, 모노(C6-C30)아릴아미노, 디(C6-C30)아릴아미노, (C1-C30)알킬카보닐, 카르복실산기, 술포닐, 할로겐, 아미노, 시아노 또는 니트로이며,
o는 1 내지 3의 정수이며,
p는 1 내지 2의 정수이며;
M은 Na, H, K 또는 Li이며;
B는 수소, 아미노, (C1-C30)알킬, (C1-C30)알콕시, (C6-C30)아릴, 모노(C1-C30)알킬아미노, 디(C1-C30)알킬아미노, 모노(C6-C30)아릴아미노 또는 디(C6-C30)아릴아미노이며;
상기 R1의 알킬, 시클로알킬, 헤테로시클로알킬, 알콕시, 아릴, 아르알킬, 헤테로아릴, 아릴옥시, 알킬옥시, 모노알킬아미노, 디알킬아미노, 모노아릴아미노, 디아릴아미노 및 알킬카보닐과 B의 알킬, 알콕시, 아릴, 모노알킬아미노, 디알킬아미노, 모노아릴아미노 및 디아릴아미노는 할로겐, 카르복실산기, 술포닐, 시아노, 니트로, 히드록시, (C1-C30)알킬, (C6-C30)아릴, (C3-C30)헤테로아릴에서 선택되는 어느 하나이상으로 더 치환될 수 있다.](4) with sodium nitrite in the presence of an acid to form a diazonium salt of the following formula
Reacting a diazonium salt of the following formula (4) with a compound of the following formula (5) to prepare a pigment additive represented by the following formula (1).
[Chemical Formula 1]
[Chemical Formula 4]
[Chemical Formula 5]
[In the formulas (1) and (4) to (5)
A is
R 1 is hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, (C3-C30) heterocycloalkyl, (C1-C30) alkoxy, (C6-C30) aryl, (C6-C30) ar ( (C1-C30) alkyl, (C3-C30) heteroaryl, (C6-C30) aryloxy, (C6-C30) arylamino, di (C6-C30) arylamino, (C1-C30) alkylcarbonyl, carboxylic acid group, sulfonyl, halogen, amino, cyano or nitro,
o is an integer from 1 to 3,
p is an integer of 1 to 2;
M is Na, H, K, or Li;
B is selected from the group consisting of hydrogen, amino, (C 1 -C 30) alkyl, (C 1 -C 30) alkoxy, (C 6 -C 30) aryl, mono (C 1 -C 30) alkylamino, ) Arylamino or di (C6-C30) arylamino;
Wherein R 1 is selected from the group consisting of alkyl, cycloalkyl, heterocycloalkyl, alkoxy, aryl, aralkyl, heteroaryl, aryloxy, alkyloxy, monoalkylamino, dialkylamino, monoarylamino, diarylamino and alkylcarbonyl and B (C1-C30) alkyl, (C6-C30) alkyl, alkoxy, aryl, monoalkylamino, dialkylamino, monoarylamino, and diarylamino groups are optionally substituted with one or more substituents selected from the group consisting of halogen, carboxylic acid group, sulfonyl, cyano, nitro, C30) aryl, (C3-C30) heteroaryl, and the like.
상기 산은 염산, 황산, 질산, 인산 및 이들의 혼합산인 안료 첨가제의 제조방법.6. The method of claim 5,
Wherein the acid is hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid and mixed acid thereof.
유기 안료는 안트라퀴논계, 디안트라퀴논계, 디케토피롤로피롤계, 퀴노프탈론계 중에서 선택되는 하나이상인 안료 분산 조성물. 8. The method of claim 7,
Wherein the organic pigment is at least one selected from anthraquinone-based, dianthraquinone-based, diketopyrrolopyrrole-based, and quinophthalone-based pigments.
안료 첨가제는 유기 안료 100중량부에 대하여 0.1 내지 30중량부로 포함되는 안료 분산 조성물.8. The method of claim 7,
Wherein the pigment additive is contained in an amount of 0.1 to 30 parts by weight based on 100 parts by weight of the organic pigment.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2005248127A (en) | 2004-03-08 | 2005-09-15 | Toyo Ink Mfg Co Ltd | Pigment dispersant, pigment composition containing the same, and pigment dispersion |
| KR100980178B1 (en) | 2005-04-19 | 2010-09-03 | 다이니치 세이카 고교 가부시키가이샤 | Pigment Dispersants and Their Uses |
| JP2011219741A (en) * | 2010-03-25 | 2011-11-04 | Mitsubishi Chemicals Corp | Pigment dispersion, colored resin composition, color filter, liquid crystal display, and organic el display |
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2014
- 2014-04-02 KR KR1020140039535A patent/KR101620843B1/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005248127A (en) | 2004-03-08 | 2005-09-15 | Toyo Ink Mfg Co Ltd | Pigment dispersant, pigment composition containing the same, and pigment dispersion |
| KR100980178B1 (en) | 2005-04-19 | 2010-09-03 | 다이니치 세이카 고교 가부시키가이샤 | Pigment Dispersants and Their Uses |
| JP2011219741A (en) * | 2010-03-25 | 2011-11-04 | Mitsubishi Chemicals Corp | Pigment dispersion, colored resin composition, color filter, liquid crystal display, and organic el display |
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