JP2017171909A - Colorant dispersant for dispersing oil-soluble dye or lipophilic pigment fine particles in water, and water-soluble ink - Google Patents
Colorant dispersant for dispersing oil-soluble dye or lipophilic pigment fine particles in water, and water-soluble ink Download PDFInfo
- Publication number
- JP2017171909A JP2017171909A JP2017053584A JP2017053584A JP2017171909A JP 2017171909 A JP2017171909 A JP 2017171909A JP 2017053584 A JP2017053584 A JP 2017053584A JP 2017053584 A JP2017053584 A JP 2017053584A JP 2017171909 A JP2017171909 A JP 2017171909A
- Authority
- JP
- Japan
- Prior art keywords
- water
- soluble
- copolymer
- colorant dispersant
- ink
- 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.)
- Granted
Links
- 239000000049 pigment Substances 0.000 title claims abstract description 58
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 40
- 239000003086 colorant Substances 0.000 title claims abstract description 30
- 239000010419 fine particle Substances 0.000 title claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title description 22
- 229920001577 copolymer Polymers 0.000 claims abstract description 38
- 239000000178 monomer Substances 0.000 claims abstract description 38
- 239000003999 initiator Substances 0.000 claims abstract description 21
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 16
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 15
- 150000001447 alkali salts Chemical class 0.000 claims abstract description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 25
- 239000000463 material Substances 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000003368 amide group Chemical group 0.000 claims description 5
- 125000000320 amidine group Chemical group 0.000 claims description 5
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 5
- 125000002560 nitrile group Chemical group 0.000 claims description 5
- 238000004040 coloring Methods 0.000 claims description 3
- -1 carboxylate salt Chemical class 0.000 description 71
- 239000000976 ink Substances 0.000 description 51
- 238000004519 manufacturing process Methods 0.000 description 46
- 239000002245 particle Substances 0.000 description 36
- 239000000975 dye Substances 0.000 description 34
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 32
- 238000003860 storage Methods 0.000 description 32
- 239000011347 resin Substances 0.000 description 31
- 229920005989 resin Polymers 0.000 description 31
- 235000014113 dietary fatty acids Nutrition 0.000 description 19
- 239000000194 fatty acid Substances 0.000 description 19
- 229930195729 fatty acid Natural products 0.000 description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 17
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 16
- 239000006185 dispersion Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 239000000843 powder Substances 0.000 description 16
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- 238000013112 stability test Methods 0.000 description 15
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 12
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 11
- 239000004094 surface-active agent Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 9
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000005587 bubbling Effects 0.000 description 4
- 239000013522 chelant Substances 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- 238000002296 dynamic light scattering Methods 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 description 3
- 239000011362 coarse particle Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 125000006353 oxyethylene group Chemical group 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 2
- JDSQBDGCMUXRBM-UHFFFAOYSA-N 2-[2-(2-butoxypropoxy)propoxy]propan-1-ol Chemical compound CCCCOC(C)COC(C)COC(C)CO JDSQBDGCMUXRBM-UHFFFAOYSA-N 0.000 description 2
- PRBXPAHXMGDVNQ-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]acetic acid Chemical compound OCCOCCOCC(O)=O PRBXPAHXMGDVNQ-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical compound C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- 229910052793 cadmium Inorganic materials 0.000 description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000003951 lactams Chemical class 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- ASWBNKHCZGQVJV-UHFFFAOYSA-N (3-hexadecanoyloxy-2-hydroxypropyl) 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C ASWBNKHCZGQVJV-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SDICTISQCKLMEB-UHFFFAOYSA-N 1,4-diamino-5-nitroanthracene-9,10-dione Chemical compound O=C1C=2C(N)=CC=C(N)C=2C(=O)C2=C1C=CC=C2[N+]([O-])=O SDICTISQCKLMEB-UHFFFAOYSA-N 0.000 description 1
- WDQFELCEOPFLCZ-UHFFFAOYSA-N 1-(2-hydroxyethyl)pyrrolidin-2-one Chemical compound OCCN1CCCC1=O WDQFELCEOPFLCZ-UHFFFAOYSA-N 0.000 description 1
- ITYXXSSJBOAGAR-UHFFFAOYSA-N 1-(methylamino)-4-(4-methylanilino)anthracene-9,10-dione Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(NC)=CC=C1NC1=CC=C(C)C=C1 ITYXXSSJBOAGAR-UHFFFAOYSA-N 0.000 description 1
- XUDJOVURIXHNRW-UHFFFAOYSA-N 1-amino-4-anilinoanthracene-9,10-dione Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=CC=C1NC1=CC=CC=C1 XUDJOVURIXHNRW-UHFFFAOYSA-N 0.000 description 1
- SSZOCHFYWWVSAI-UHFFFAOYSA-N 1-bromo-2-ethenylbenzene Chemical compound BrC1=CC=CC=C1C=C SSZOCHFYWWVSAI-UHFFFAOYSA-N 0.000 description 1
- KQJQPCJDKBKSLV-UHFFFAOYSA-N 1-bromo-3-ethenylbenzene Chemical compound BrC1=CC=CC(C=C)=C1 KQJQPCJDKBKSLV-UHFFFAOYSA-N 0.000 description 1
- WGGLDBIZIQMEGH-UHFFFAOYSA-N 1-bromo-4-ethenylbenzene Chemical compound BrC1=CC=C(C=C)C=C1 WGGLDBIZIQMEGH-UHFFFAOYSA-N 0.000 description 1
- RSPAWCCGXDUDMM-UHFFFAOYSA-N 1-but-1-enyl-4-ethenylbenzene Chemical compound CCC=CC1=CC=C(C=C)C=C1 RSPAWCCGXDUDMM-UHFFFAOYSA-N 0.000 description 1
- BOVQCIDBZXNFEJ-UHFFFAOYSA-N 1-chloro-3-ethenylbenzene Chemical compound ClC1=CC=CC(C=C)=C1 BOVQCIDBZXNFEJ-UHFFFAOYSA-N 0.000 description 1
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
- OEVVKKAVYQFQNV-UHFFFAOYSA-N 1-ethenyl-2,4-dimethylbenzene Chemical compound CC1=CC=C(C=C)C(C)=C1 OEVVKKAVYQFQNV-UHFFFAOYSA-N 0.000 description 1
- VTPNYMSKBPZSTF-UHFFFAOYSA-N 1-ethenyl-2-ethylbenzene Chemical compound CCC1=CC=CC=C1C=C VTPNYMSKBPZSTF-UHFFFAOYSA-N 0.000 description 1
- YNQXOOPPJWSXMW-UHFFFAOYSA-N 1-ethenyl-2-fluorobenzene Chemical compound FC1=CC=CC=C1C=C YNQXOOPPJWSXMW-UHFFFAOYSA-N 0.000 description 1
- YBHWIVKIQYJYOH-UHFFFAOYSA-N 1-ethenyl-2-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC=C1C=C YBHWIVKIQYJYOH-UHFFFAOYSA-N 0.000 description 1
- XKMDZVINHIFHLY-UHFFFAOYSA-N 1-ethenyl-3,5-dimethylbenzene Chemical compound CC1=CC(C)=CC(C=C)=C1 XKMDZVINHIFHLY-UHFFFAOYSA-N 0.000 description 1
- XHUZSRRCICJJCN-UHFFFAOYSA-N 1-ethenyl-3-ethylbenzene Chemical compound CCC1=CC=CC(C=C)=C1 XHUZSRRCICJJCN-UHFFFAOYSA-N 0.000 description 1
- ZJSKEGAHBAHFON-UHFFFAOYSA-N 1-ethenyl-3-fluorobenzene Chemical compound FC1=CC=CC(C=C)=C1 ZJSKEGAHBAHFON-UHFFFAOYSA-N 0.000 description 1
- PECUPOXPPBBFLU-UHFFFAOYSA-N 1-ethenyl-3-methoxybenzene Chemical compound COC1=CC=CC(C=C)=C1 PECUPOXPPBBFLU-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- BYYLJVQCWRRFMP-UHFFFAOYSA-N 1-ethenyl-3-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC(C=C)=C1 BYYLJVQCWRRFMP-UHFFFAOYSA-N 0.000 description 1
- WHFHDVDXYKOSKI-UHFFFAOYSA-N 1-ethenyl-4-ethylbenzene Chemical compound CCC1=CC=C(C=C)C=C1 WHFHDVDXYKOSKI-UHFFFAOYSA-N 0.000 description 1
- KEZDVVCDQRDBDN-UHFFFAOYSA-N 1-ethenyl-4-fluoro-2-methylbenzene Chemical compound CC1=CC(F)=CC=C1C=C KEZDVVCDQRDBDN-UHFFFAOYSA-N 0.000 description 1
- JWVTWJNGILGLAT-UHFFFAOYSA-N 1-ethenyl-4-fluorobenzene Chemical compound FC1=CC=C(C=C)C=C1 JWVTWJNGILGLAT-UHFFFAOYSA-N 0.000 description 1
- QQHQTCGEZWTSEJ-UHFFFAOYSA-N 1-ethenyl-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(C=C)C=C1 QQHQTCGEZWTSEJ-UHFFFAOYSA-N 0.000 description 1
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 1
- QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 description 1
- GZMAAYIALGURDQ-UHFFFAOYSA-N 2-(2-hexoxyethoxy)ethanol Chemical compound CCCCCCOCCOCCO GZMAAYIALGURDQ-UHFFFAOYSA-N 0.000 description 1
- JSMWMVVVPBPVPX-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxymethyl)butanedioic acid Chemical compound CC(=C)C(=O)OCC(C(O)=O)CC(O)=O JSMWMVVVPBPVPX-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
- FWLHAQYOFMQTHQ-UHFFFAOYSA-N 2-N-[8-[[8-(4-aminoanilino)-10-phenylphenazin-10-ium-2-yl]amino]-10-phenylphenazin-10-ium-2-yl]-8-N,10-diphenylphenazin-10-ium-2,8-diamine hydroxy-oxido-dioxochromium Chemical compound O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.Nc1ccc(Nc2ccc3nc4ccc(Nc5ccc6nc7ccc(Nc8ccc9nc%10ccc(Nc%11ccccc%11)cc%10[n+](-c%10ccccc%10)c9c8)cc7[n+](-c7ccccc7)c6c5)cc4[n+](-c4ccccc4)c3c2)cc1 FWLHAQYOFMQTHQ-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- ISRGONDNXBCDBM-UHFFFAOYSA-N 2-chlorostyrene Chemical compound ClC1=CC=CC=C1C=C ISRGONDNXBCDBM-UHFFFAOYSA-N 0.000 description 1
- CKSAKVMRQYOFBC-UHFFFAOYSA-N 2-cyanopropan-2-yliminourea Chemical compound N#CC(C)(C)N=NC(N)=O CKSAKVMRQYOFBC-UHFFFAOYSA-N 0.000 description 1
- DBWWINQJTZYDFK-UHFFFAOYSA-N 2-ethenyl-1,4-dimethylbenzene Chemical compound CC1=CC=C(C)C(C=C)=C1 DBWWINQJTZYDFK-UHFFFAOYSA-N 0.000 description 1
- LYPGJGCIPQYQBW-UHFFFAOYSA-N 2-methyl-2-[[2-methyl-1-oxo-1-(prop-2-enylamino)propan-2-yl]diazenyl]-n-prop-2-enylpropanamide Chemical compound C=CCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCC=C LYPGJGCIPQYQBW-UHFFFAOYSA-N 0.000 description 1
- 229940044120 2-n-octyl-4-isothiazolin-3-one Drugs 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- BYLRZCIZXYKLQL-UHFFFAOYSA-N 3-[3-(3-sulfopropoxycarbonyl)but-3-enoyloxy]propane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCOC(=O)CC(=C)C(=O)OCCCS(O)(=O)=O BYLRZCIZXYKLQL-UHFFFAOYSA-N 0.000 description 1
- QJRKNPUNWGNXQR-UHFFFAOYSA-N 3-butyl-2-phenylphenol Chemical compound CCCCC1=CC=CC(O)=C1C1=CC=CC=C1 QJRKNPUNWGNXQR-UHFFFAOYSA-N 0.000 description 1
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- QPQKUYVSJWQSDY-UHFFFAOYSA-N 4-phenyldiazenylaniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC=C1 QPQKUYVSJWQSDY-UHFFFAOYSA-N 0.000 description 1
- 229940100484 5-chloro-2-methyl-4-isothiazolin-3-one Drugs 0.000 description 1
- 241000557626 Corvus corax Species 0.000 description 1
- 241000721047 Danaus plexippus Species 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- 241001594894 Mesites Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 239000004288 Sodium dehydroacetate Substances 0.000 description 1
- 239000004283 Sodium sorbate Substances 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- JZFICWYCTCCINF-UHFFFAOYSA-N Thiadiazin Chemical compound S=C1SC(C)NC(C)N1CCN1C(=S)SC(C)NC1C JZFICWYCTCCINF-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 1
- QAFYDZVGLWZHHG-UHFFFAOYSA-L [Cl-].[Cl-].[Ca++].O=c1ccs[nH]1 Chemical compound [Cl-].[Cl-].[Ca++].O=c1ccs[nH]1 QAFYDZVGLWZHHG-UHFFFAOYSA-L 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- XREZMAAQVYVESP-UHFFFAOYSA-N acetyloxymethyl 2-[n-[2-(acetyloxymethoxy)-2-oxoethyl]-2-[2-[2-[bis[2-(acetyloxymethoxy)-2-oxoethyl]amino]-4-fluorophenoxy]ethoxy]-5-fluoroanilino]acetate Chemical compound CC(=O)OCOC(=O)CN(CC(=O)OCOC(C)=O)C1=CC(F)=CC=C1OCCOC1=CC=C(F)C=C1N(CC(=O)OCOC(C)=O)CC(=O)OCOC(C)=O XREZMAAQVYVESP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 239000000981 basic dye Substances 0.000 description 1
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 1
- 239000003876 biosurfactant Substances 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- ABBZJHFBQXYTLU-UHFFFAOYSA-N but-3-enamide Chemical compound NC(=O)CC=C ABBZJHFBQXYTLU-UHFFFAOYSA-N 0.000 description 1
- QAJHFVRPDSGYSZ-UHFFFAOYSA-N butyl 2-phenylbenzenesulfonate Chemical compound CCCCOS(=O)(=O)C1=CC=CC=C1C1=CC=CC=C1 QAJHFVRPDSGYSZ-UHFFFAOYSA-N 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- ZNUJLBVUZKNDOW-UHFFFAOYSA-L calcium;2-methyl-1,2-thiazol-3-one;dichloride Chemical compound [Cl-].[Cl-].[Ca+2].CN1SC=CC1=O ZNUJLBVUZKNDOW-UHFFFAOYSA-L 0.000 description 1
- ZLJXBBQYDUERBP-UHFFFAOYSA-L calcium;5-chloro-2-methyl-1,2-thiazol-3-one;dichloride Chemical compound [Cl-].[Cl-].[Ca+2].CN1SC(Cl)=CC1=O ZLJXBBQYDUERBP-UHFFFAOYSA-L 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- PXOZAFXVEWKXED-UHFFFAOYSA-N chembl1590721 Chemical compound C1=CC(NC(=O)C)=CC=C1N=NC1=CC(C)=CC=C1O PXOZAFXVEWKXED-UHFFFAOYSA-N 0.000 description 1
- DHNRXBZYEKSXIM-UHFFFAOYSA-N chloromethylisothiazolinone Chemical compound CN1SC(Cl)=CC1=O DHNRXBZYEKSXIM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- ISRJTGUYHVPAOR-UHFFFAOYSA-N dihydrodicyclopentadienyl acrylate Chemical compound C1CC2C3C(OC(=O)C=C)C=CC3C1C2 ISRJTGUYHVPAOR-UHFFFAOYSA-N 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 description 1
- 150000004662 dithiols Chemical class 0.000 description 1
- LLRANSBEYQZKFY-UHFFFAOYSA-N dodecanoic acid;propane-1,2-diol Chemical compound CC(O)CO.CCCCCCCCCCCC(O)=O LLRANSBEYQZKFY-UHFFFAOYSA-N 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003752 hydrotrope Substances 0.000 description 1
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical class C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 229910017053 inorganic salt Chemical class 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- MOUPNEIJQCETIW-UHFFFAOYSA-N lead chromate Chemical compound [Pb+2].[O-][Cr]([O-])(=O)=O MOUPNEIJQCETIW-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- JGHGKNIEYCBHJY-UHFFFAOYSA-L magnesium;5-chloro-2-methyl-1,2-thiazol-3-one;dichloride Chemical compound [Mg+2].[Cl-].[Cl-].CN1SC(Cl)=CC1=O JGHGKNIEYCBHJY-UHFFFAOYSA-L 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- SFBTTWXNCQVIEC-UHFFFAOYSA-N o-Vinylanisole Chemical compound COC1=CC=CC=C1C=C SFBTTWXNCQVIEC-UHFFFAOYSA-N 0.000 description 1
- JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- HDBWAWNLGGMZRQ-UHFFFAOYSA-N p-Vinylbiphenyl Chemical compound C1=CC(C=C)=CC=C1C1=CC=CC=C1 HDBWAWNLGGMZRQ-UHFFFAOYSA-N 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229940110337 pigment blue 1 Drugs 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- ARENMZZMCSLORU-UHFFFAOYSA-N propan-2-yl naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OC(C)C)=CC=CC2=C1 ARENMZZMCSLORU-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- FCBUKWWQSZQDDI-UHFFFAOYSA-N rhamnolipid Chemical compound CCCCCCCC(CC(O)=O)OC(=O)CC(CCCCCCC)OC1OC(C)C(O)C(O)C1OC1C(O)C(O)C(O)C(C)O1 FCBUKWWQSZQDDI-UHFFFAOYSA-N 0.000 description 1
- QPRQEDXDYOZYLA-UHFFFAOYSA-N sec-pentyl alcohol Natural products CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229940079839 sodium dehydroacetate Drugs 0.000 description 1
- 235000019259 sodium dehydroacetate Nutrition 0.000 description 1
- DVQHRBFGRZHMSR-UHFFFAOYSA-N sodium methyl 2,2-dimethyl-4,6-dioxo-5-(N-prop-2-enoxy-C-propylcarbonimidoyl)cyclohexane-1-carboxylate Chemical compound [Na+].C=CCON=C(CCC)[C-]1C(=O)CC(C)(C)C(C(=O)OC)C1=O DVQHRBFGRZHMSR-UHFFFAOYSA-N 0.000 description 1
- LROWVYNUWKVTCU-STWYSWDKSA-M sodium sorbate Chemical compound [Na+].C\C=C\C=C\C([O-])=O LROWVYNUWKVTCU-STWYSWDKSA-M 0.000 description 1
- 235000019250 sodium sorbate Nutrition 0.000 description 1
- DSOWAKKSGYUMTF-GZOLSCHFSA-M sodium;(1e)-1-(6-methyl-2,4-dioxopyran-3-ylidene)ethanolate Chemical compound [Na+].C\C([O-])=C1/C(=O)OC(C)=CC1=O DSOWAKKSGYUMTF-GZOLSCHFSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 229920005792 styrene-acrylic resin Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
Abstract
Description
本発明は、油溶性染料あるいは親油性顔料微粒子を水に分散するための色材分散剤、および水溶性インキに関する。 The present invention relates to a colorant dispersant for dispersing oil-soluble dyes or lipophilic pigment fine particles in water, and a water-soluble ink.
特許文献１に示すように、油溶性染料あるいは親油性顔料微粒子を水に分散するための分散剤として、芳香族ビニル単量体と不飽和カルボン酸単量体の共重合体のアルカリ塩を使用することができることが知られている。
芳香族構造は油溶性染料あるいは親油性顔料微粒子への親和性を高めカルボン酸塩は水に対する親和性を高める。
前記共重合体塩を、油溶性染料あるいは親油性顔料微粒子の分散剤とすることにより水中で安定なコロイドとすることができる。
As shown in Patent Document 1, an alkali salt of a copolymer of an aromatic vinyl monomer and an unsaturated carboxylic acid monomer is used as a dispersant for dispersing oil-soluble dyes or lipophilic pigment fine particles in water. It is known that you can.
The aromatic structure increases the affinity for oil-soluble dyes or lipophilic pigment particles, and the carboxylate salt increases the affinity for water.
A stable colloid in water can be obtained by using the copolymer salt as a dispersant for oil-soluble dyes or lipophilic pigment fine particles.
一方、前記共重合体が過酸化物系開始剤で重合された共重合体であると、共重合体の末端がアルコキシ基となってしまい油溶性染料あるいは親油性顔料微粒子に対する親和性は低下してしまう。 On the other hand, if the copolymer is a copolymer polymerized with a peroxide-based initiator, the terminal of the copolymer becomes an alkoxy group, and the affinity for oil-soluble dyes or lipophilic pigment fine particles decreases. End up.
本発明はかかる事情を鑑みてなされたものであり、分子鎖両端に油溶性染料あるいは親油性顔料微粒子に対する親和性構造を持った構造を有する共重合体を有する色材分散剤、および当該色材分散剤を用いた水溶性インキを得ることを目的とする。 The present invention has been made in view of such circumstances, and a colorant dispersant having a copolymer having a structure having an affinity structure for oil-soluble dyes or lipophilic pigment fine particles at both ends of a molecular chain, and the colorant The object is to obtain a water-soluble ink using a dispersant.
本発明の第１態様に係る色材分散剤は、アゾ系開始剤で重合された芳香族ビニル単量体単位と不飽和カルボン酸単量体単位とを有する共重合体のアルカリ塩を備える。 The colorant dispersant according to the first aspect of the present invention includes an alkali salt of a copolymer having an aromatic vinyl monomer unit and an unsaturated carboxylic acid monomer unit polymerized with an azo initiator.
前記共重合体の末端の少なくとも一方に窒素が存在していてもよい。 Nitrogen may be present at least at one end of the copolymer.
前記アゾ系開始剤は、アゾ基以外の窒素を備えていてもよい。 The azo initiator may include nitrogen other than an azo group.
前記アゾ系開始剤は、アミド基、ニトリル基、アミジン基およびイミダゾリン基のうち少なくとも一つをさらに有していてもよい。 The azo initiator may further have at least one of an amide group, a nitrile group, an amidine group, and an imidazoline group.
前記共重合体の重量平均分子量が２０００〜１０００００の範囲であってもよい。 The range of 2000-100000 may be sufficient as the weight average molecular weight of the said copolymer.
前記共重合体のうちの、前記芳香族ビニル単量体単位の質量比率をｎと表し、前記不飽和カルボン酸単量体単位の質量比率をｍと表したとき、ｎが５〜７４であり、ｍが２５〜５０であり、ｎ＋ｍ≦１００であってもよい。 When the mass ratio of the aromatic vinyl monomer unit in the copolymer is expressed as n and the mass ratio of the unsaturated carboxylic acid monomer unit is expressed as m, n is 5 to 74. , M may be 25 to 50, and n + m ≦ 100 may be satisfied.
本発明の第２態様に係る水溶性インキは、上記態様に係る色材分散剤と、油溶性染料および親油性顔料微粒子のうち少なくとも一つと、を含む。 The water-soluble ink according to the second aspect of the present invention includes the color material dispersant according to the above aspect and at least one of an oil-soluble dye and lipophilic pigment fine particles.
本発明の上記態様に係る色材分散剤および水溶性インキによれば、油溶性染料あるいは親油性顔料微粒子の水溶性インキ中における分散安定性が良好になる。
また、末端に開始剤由来の窒素が存在すること、および、アミド基やニトリル基、アミジン基、イミダゾリン基などのアゾ基以外の窒素を持つアゾ系開始剤の使用によりさらに油溶性染料あるいは親油性顔料微粒子（特に含窒素染料、顔料）への親和性がさらに高まる。
また、上記態様に係る色材分散剤および水溶性インキによれば、分子量をある程度小さくし分子数を増やし、共重合体末端の数を増加させているので、油溶性染料への親和性が高まる。
According to the colorant dispersant and the water-soluble ink according to the above aspect of the present invention, the dispersion stability of the oil-soluble dye or the lipophilic pigment fine particles in the water-soluble ink is improved.
In addition, the presence of initiator-derived nitrogen at the end, and the use of azo-based initiators with nitrogen other than azo groups such as amide group, nitrile group, amidine group, imidazoline group, etc. The affinity for fine pigment particles (particularly nitrogen-containing dyes and pigments) is further increased.
In addition, according to the colorant dispersant and the water-soluble ink according to the above aspect, the molecular weight is reduced to some extent, the number of molecules is increased, and the number of copolymer ends is increased, so the affinity for oil-soluble dyes is increased. .
以下、好適な実施形態に基づいて、本発明を説明する。 Hereinafter, the present invention will be described based on preferred embodiments.
（色材分散剤）
本発明の一実施形態に係る色材分散剤は、アゾ系開始剤で重合された芳香族ビニル単量体単位と不飽和カルボン酸単量体単位とを有する共重合体のアルカリ塩を備える。
本実施形態に係る色材分散剤においては、油溶性染料あるいは親油性顔料微粒子を水に分散するための分散剤として、芳香族ビニル単量体と不飽和カルボン酸単量体の共重合体のアルカリ塩を使用することができる。
芳香族構造は油溶性染料あるいは親油性顔料微粒子への親和性を高めカルボン酸塩は水に対する親和性を高める。
前記共重合体塩を、油溶性染料あるいは親油性顔料微粒子の分散剤とすることにより水中で安定なコロイドとすることができる。
(Coloring material dispersant)
The colorant dispersant according to an embodiment of the present invention includes an alkali salt of a copolymer having an aromatic vinyl monomer unit and an unsaturated carboxylic acid monomer unit polymerized with an azo initiator.
In the colorant dispersant according to this embodiment, a copolymer of an aromatic vinyl monomer and an unsaturated carboxylic acid monomer is used as a dispersant for dispersing oil-soluble dyes or lipophilic pigment fine particles in water. Alkali salts can be used.
The aromatic structure increases the affinity for oil-soluble dyes or lipophilic pigment particles, and the carboxylate salt increases the affinity for water.
A stable colloid in water can be obtained by using the copolymer salt as a dispersant for oil-soluble dyes or lipophilic pigment fine particles.
一方、前記共重合体が過酸化物系開始剤で重合された共重合体であると、共重合体の末端がアルコキシ基となってしまい油溶性染料あるいは親油性顔料微粒子に対する親和性は低下してしまう。 On the other hand, if the copolymer is a copolymer polymerized with a peroxide-based initiator, the terminal of the copolymer becomes an alkoxy group, and the affinity for oil-soluble dyes or lipophilic pigment fine particles decreases. End up.
よって色材分散剤の安定性を高めるために、本実施形態に係る色材分散剤においては、分子鎖両端に油溶性染料あるいは親油性顔料微粒子に対する親和性構造を持った構造が必要であるため、共重合体をアゾ系開始剤で重合している。
すなわち、本実施形態に係る色材分散剤においては、共重合体の末端の少なくとも一方に窒素が存在することが好ましい。
Therefore, in order to improve the stability of the color material dispersant, the color material dispersant according to the present embodiment requires a structure having an affinity structure for oil-soluble dyes or lipophilic pigment fine particles at both ends of the molecular chain. The copolymer is polymerized with an azo initiator.
That is, in the colorant dispersant according to this embodiment, it is preferable that nitrogen is present at at least one of the ends of the copolymer.
また、末端に開始剤由来の窒素が存在することによりさらに油溶性染料あるいは親油性顔料微粒子（特に含窒素染料、顔料）への親和性がさらに高まると考えられるため、アゾ基以外の窒素を持つアゾ系開始剤の使用が特に望ましい。アゾ基以外の窒素を持つ構造（官能基）としてはアミド基やニトリル基、アミジン基、イミダゾリン基などが挙げられる。
すなわち、本実施形態に係る色材分散剤においては、アゾ系開始剤は、官能基として、アゾ基に加えて、アミド基、ニトリル基、アミジン基およびイミダゾリン基のうち少なくとも一つをさらに有していてもよい。
In addition, the presence of nitrogen derived from the initiator at the end further increases the affinity for oil-soluble dyes or lipophilic pigment fine particles (particularly nitrogen-containing dyes and pigments), and therefore has nitrogen other than azo groups. The use of an azo initiator is particularly desirable. Examples of the structure (functional group) having nitrogen other than the azo group include an amide group, a nitrile group, an amidine group, and an imidazoline group.
That is, in the colorant dispersant according to the present embodiment, the azo initiator further has at least one of an amide group, a nitrile group, an amidine group, and an imidazoline group as a functional group in addition to the azo group. It may be.
油溶性染料への親和性を高めるには共重合体の末端の数が多いほどよい。したがって分子量をある程度小さくし分子数を増やし、共重合体末端の数を増加させることが肝要である。 In order to increase the affinity for the oil-soluble dye, the larger the number of terminals of the copolymer, the better. Therefore, it is important to reduce the molecular weight to some extent, increase the number of molecules, and increase the number of copolymer ends.
これらのことから、本実施形態に係る油溶性染料あるいは親油性顔料微粒子を水に分散するための色材分散剤としては、アゾ系開始剤を用い重合された芳香族ビニル単量体と不飽和カルボン酸単量体の共重合体のアルカリ塩が適当である。 From these facts, as a colorant dispersant for dispersing the oil-soluble dye or lipophilic pigment fine particles according to the present embodiment in water, an aromatic vinyl monomer polymerized using an azo initiator and unsaturated An alkali salt of a copolymer of carboxylic acid monomers is suitable.
（水溶性インキ）
本発明の一実施形態に係る水溶性インキは上記色材分散剤と、油溶性染料あるいは親油性顔料微粒子を含んだ分散液に、水性溶媒、樹脂、界面活性剤、その他の添加剤などを加えて均一に混合することにより製造できる。
(Water-soluble ink)
The water-soluble ink according to an embodiment of the present invention is obtained by adding an aqueous solvent, a resin, a surfactant, other additives, etc. to the dispersion containing the colorant dispersant and the oil-soluble dye or lipophilic pigment fine particles. Can be produced by mixing uniformly.
また、本実施形態に係る水溶性インキは、所望の濃度に希釈して、自動車や建材用の塗料分野や、オフセットインキ、グラビアインキ、フレキソインキ、シルクスクリーンインキ等の印刷インキ分野、あるいはインクジェット記録用水性インク分野等様々な用途に使用することができる。 In addition, the water-soluble ink according to the present embodiment is diluted to a desired concentration to be used in the paint field for automobiles and building materials, the printing ink field such as offset ink, gravure ink, flexo ink, silk screen ink, or ink jet recording. It can be used for various applications such as water-based inks.
本実施形態に係る水溶性インキにおいては、添加剤を必要に応じて添加することができる。
例えば、表面張力調整剤、ヒドロトロープ剤、ｐＨ調整剤、粘度調整剤、防錆剤、酸化防止剤、還元防止剤、光安定剤、キレート化剤、消泡剤等である。
In the water-soluble ink according to the present embodiment, an additive can be added as necessary.
For example, surface tension adjusters, hydrotropes, pH adjusters, viscosity adjusters, rust inhibitors, antioxidants, reduction inhibitors, light stabilizers, chelating agents, antifoaming agents, and the like.
（共重合体の単量体の比率の範囲）
本実施形態に係る色材分散剤において用いられる共重合体の単量体の質量比率の範囲は、共重合体を構成する全ての構成単位を１００質量部としたとき、（芳香族ビニル単量体（芳香族ビニル単量体単位））の質量比率をｎと表し、（不飽和カルボン酸単量体（不飽和カルボン酸単量体単位））の質量比率をｍと表したとき、以下に示す比率の範囲である。
（芳香族ビニル単量体）ｎ‐（不飽和カルボン酸単量体）ｍ
ｎ：５〜７４
ｍ：２５〜５０
ただし、ｎ＋ｍ≦１００である。
すなわち、本実施形態に係る色材分散剤においては、前記共重合体のうちの、前記芳香族ビニル単量体単位の質量比率をｎと表し、前記不飽和カルボン酸単量体単位の質量比率をｍと表したとき、ｎが５〜７４であり、ｍが２５〜５０であり、ｎ＋ｍ≦１００であってもよい。
なお、特性を妨げない範囲でその他の単量体を含めてもよい。
(Range of copolymer monomer ratio)
The range of the mass ratio of the monomer of the copolymer used in the colorant dispersant according to the present embodiment is such that when all the structural units constituting the copolymer are 100 parts by mass, (aromatic vinyl monomer) Body (aromatic vinyl monomer unit)) is expressed as n, and (unsaturated carboxylic acid monomer (unsaturated carboxylic acid monomer unit)) is expressed as m. It is the range of the ratio shown.
(Aromatic vinyl monomer) n- (Unsaturated carboxylic acid monomer) m
n: 5 to 74
m: 25-50
However, it is n + m <= 100.
That is, in the colorant dispersant according to this embodiment, the mass ratio of the aromatic vinyl monomer unit in the copolymer is represented by n, and the mass ratio of the unsaturated carboxylic acid monomer unit. When m is expressed as m, n may be 5 to 74, m may be 25 to 50, and n + m ≦ 100.
In addition, you may include another monomer in the range which does not disturb a characteristic.
（芳香族ビニル単量体）
本実施形態に係る色材分散剤において、原料として用いられる芳香族ビニル単量体としては、スチレン、アルキルスチレン、アリールスチレン、ハロゲン化スチレン、アルコキシスチレン、アルキルスチレンの具体例としては、ｏ−メチルスチレン、ｍ−メチルスチレン、ｐ−メチルスチレン、ｏ−エチルスチレン、ｍ−エチルスチレン、ｐ−エチルスチレン、ｏ−ｎ−プロピレンスチレン、ｍ−ｎ−プロピルスチレン、ｐ−ｎ−プロピルスチレン、ｏ−イソプロピルスチレン、ｍ−イソプロピルスチレン、ｐ−イソプロピルスチレン、ｍ−ｎ−ブチルスチレン、ｐ−ｎ−ブチルスチレン、ｐ−ｔｅｒｔ−ブチルスチレン、４−ブテニルスチレン、２，４−ジメチルスチレン、２，５−ジメチルスチレン、３，５−ジメチルスチレン、メシチルスチレン等が挙げられる。
(Aromatic vinyl monomer)
In the colorant dispersant according to this embodiment, examples of the aromatic vinyl monomer used as a raw material include styrene, alkyl styrene, aryl styrene, halogenated styrene, alkoxy styrene, and alkyl styrene. Styrene, m-methyl styrene, p-methyl styrene, o-ethyl styrene, m-ethyl styrene, p-ethyl styrene, on-propylene styrene, mn-propyl styrene, pn-propyl styrene, o- Isopropyl styrene, m-isopropyl styrene, p-isopropyl styrene, mn-butyl styrene, pn-butyl styrene, p-tert-butyl styrene, 4-butenyl styrene, 2,4-dimethyl styrene, 2,5 -Dimethylstyrene, 3,5-dimethylstyrene, mesit Styrene.
アリールスチレンの具体例としては、ｐ−フェニルスチレン等が挙げられる。
ハロゲン化スチレンの具体例としては、ｏ−フルオロスチレン、ｍ−フルオロスチレン、ｐ−フルオロスチレン、ｏ−クロロスチレン、ｍ−クロロスチレン、ｐ−クロロスチレン、ｏ−ブロモスチレン、ｍ−ブロモスチレン、ｐ−ブロモスチレン、ｏ−メチル−ｐ−フルオロスチレン等が挙げられる。
Specific examples of the aryl styrene include p-phenyl styrene.
Specific examples of the halogenated styrene include o-fluorostyrene, m-fluorostyrene, p-fluorostyrene, o-chlorostyrene, m-chlorostyrene, p-chlorostyrene, o-bromostyrene, m-bromostyrene, p -Bromostyrene, o-methyl-p-fluorostyrene and the like.
アルコキシスチレンの具体例としては、ｏ−メトキシスチレン、ｍ−メトキシスチレン、ｐ−メトキシスチレン等が挙げられる。 Specific examples of alkoxystyrene include o-methoxystyrene, m-methoxystyrene, p-methoxystyrene and the like.
上記芳香族ビニル単量体は、１種を単独で用いてもよく、２種以上を組み合わせて用いてもよい。 The said aromatic vinyl monomer may be used individually by 1 type, and may be used in combination of 2 or more type.
（メタ）アクリレートとは、メタクリレートおよびアクリレートの総称である。また、（メタ）アクリル酸は、メタクリル酸およびアクリル酸の総称である。
不飽和カルボン酸単量体としては、アクリル酸、メタクリル酸、クロトン酸、イタコン酸、マレイン酸、フマル酸、シトラコン酸、２−メタクリロイルオキシメチルコハク酸等が挙げられる。不飽和スルホン酸モノマーとして具体的には、スチレンスルホン酸、２−アクリルアミド−２−メチルプロパンスルホン酸、３−スルホプロピル（メタ）アクリレート、ビス−（３−スルホプロピル）−イタコン酸エステル等が挙げられる。
(Meth) acrylate is a general term for methacrylate and acrylate. Moreover, (meth) acrylic acid is a general term for methacrylic acid and acrylic acid.
Examples of the unsaturated carboxylic acid monomer include acrylic acid, methacrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, citraconic acid, and 2-methacryloyloxymethyl succinic acid. Specific examples of the unsaturated sulfonic acid monomer include styrene sulfonic acid, 2-acrylamido-2-methylpropane sulfonic acid, 3-sulfopropyl (meth) acrylate, and bis- (3-sulfopropyl) -itaconate. It is done.
上記不飽和カルボン酸モノマーは、１種を単独で用いてもよく、２種以上を組み合わせて用いてもよい。 The said unsaturated carboxylic acid monomer may be used individually by 1 type, and may be used in combination of 2 or more type.
その他の単量体としては不飽和カルボン酸エステル単量体が挙げられる。
不飽和カルボン酸エステル単量体としては、単官能（メタ）アクリレートが挙げられ、具体的には、（メタ）アクリル酸メチル、（メタ）アクリル酸エチル、（メタ）アクリル酸プロピル、（メタ）アクリル酸ブチル、（メタ）アクリル酸ペンチル、（メタ）アクリル酸ヘキシル、（メタ）アクリル酸へプチル、（メタ）アクリル酸オクチル等の（メタ）アクリル酸アルキルエステル；（メタ）アクリル酸２−メトキシエチル、（メタ）アクリル酸２−エトキシエチル、（メタ）アクリル酸２−（ｎ−プロポキシ）エチル、（メタ）アクリル酸２−（ｎ−ブトキシ）エチル、（メタ）アクリル酸３−メトキシプロピル、（メタ）アクリル酸３−エトキシプロピル、（メタ）アクリル酸２−（ｎ−プロポキシ）プロピル、（メタ）アクリル酸２−（ｎ−ブトキシ）プロピル等の（メタ）アクリル酸アルコキシアルキルエステル；（メタ）アクリル酸シクロヘキシル、（メタ）アクリル酸ジシクロペンタニル、（メタ）アクリル酸イソボルニル等の脂環構造を有する（メタ）アクリル酸エステルなどが挙げられる。
不飽和カルボン酸エステルは、１種単独で用いてもよく、２種以上を併用してもよい。
Examples of other monomers include unsaturated carboxylic acid ester monomers.
Examples of unsaturated carboxylic acid ester monomers include monofunctional (meth) acrylates, specifically, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, (meth) (Meth) acrylic acid alkyl esters such as butyl acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate; 2-methoxy (meth) acrylate Ethyl, 2-ethoxyethyl (meth) acrylate, 2- (n-propoxy) ethyl (meth) acrylate, 2- (n-butoxy) ethyl (meth) acrylate, 3-methoxypropyl (meth) acrylate, (Meth) acrylic acid 3-ethoxypropyl, (meth) acrylic acid 2- (n-propoxy) propyl, (meth) acrylic acid 2 (Meth) acrylic acid alkoxyalkyl ester such as (n-butoxy) propyl; (meth) having an alicyclic structure such as cyclohexyl (meth) acrylate, dicyclopentanyl (meth) acrylate, isobornyl (meth) acrylate Examples include acrylic acid esters.
Unsaturated carboxylic acid ester may be used individually by 1 type, and may use 2 or more types together.
共重合性の観点から、スチレン−アクリル酸ブチル-（メタ）アクリル酸、スチレン−アクリル酸２エチルヘキシル−（メタ）アクリル酸などが好ましい。 From the viewpoint of copolymerization, styrene-butyl acrylate- (meth) acrylic acid, styrene-2-ethylhexyl acrylate- (meth) acrylic acid, and the like are preferable.
（開始剤）
本実施形態に係る色材分散剤において用いられる開始剤としては、例えば、以下の化合物が挙げられる。
具体的には、２，２’−ａｚｏｂｉｓ〔Ｎ−（２−ｐｒｏｐｅｎｙｌ）−２−ｍｅｔｙｌｐｒｏｐｉｏｎａｍｉｄｅ〕、１−〔（１−Ｃｙａｎｏ−１−ｍｅｔｈｙｌｅｔｈｙｌ）ａｚｏ〕ｆｏｒｍａｍｉｄｅ、１，１’−ａｚｏｂｉｓ（ｃｙｃｌｏｈｅｘａｎｅ−１−ｃａｒｂｏｎｉｔｒｉｌｅ）、２，２’−ａｚｏｂｉｓ（２−ｍｅｔｈｙｌｂｕｔｙｒｏｎｉｔｒｉｌｅ）、２，２’−ａｚｏｂｉｓ（ｉｓｏｂｕｔｙｒｏｎｉｔｒｉｌｅ）、２，２’−ａｚｏｂｉｓ（２，４−ｄｉｍｅｔｈｙｌｖａｌｅｒｏｎｉｔｒｉｌｅ）、２，２’−ａｚｏｂｉｓ（４−ｍｅｔｈｏｘｙ−２，４−ｄｉｍｅｔｈｙｌｖａｌｅｒｏｎｉｔｒｉｌｅ）、Ｄｉｍｅｔｈｙｌ ２，２’−ａｚｏｂｉｓ（ｉｓｏｂｕｔｙｒａｔｅ）、２，２’−ａｚｏｂｉｓ〔２−（２−ｉｍｉｄａｚｏｌｉｎ−２−ｙｌ）ｐｒｏｐａｎｅ〕、２，２’−ａｚｏｂｉｓ（２−ａｍｉｄｉｎｏｐｒｏｐａｎｅ）ｄｉｈｙｄｒｏｃｈｌｏｒｉｄｅ、２，２’ａｚｏｂｉｓ（Ｎ−ｂｕｔｙｌ−２−ｍｅｔｈｙｌｐｒｏｐｉｏｎａｍｉｄｅ）、２，２’−ａｚｏｂｉｓ〔Ｎ−（２−ｐｒｏｐｅｎｙｌ）−２−ｍｅｔｈｙｌｐｒｏｐｉｏｎａｍｉｄｅ〕等のアゾ系開始剤が挙げられる。
(Initiator)
Examples of the initiator used in the color material dispersant according to this embodiment include the following compounds.
Specifically, 2,2′-azobis [N- (2-propenyl) -2-methylpropionamide], 1-[(1-Cyano-1-methylethyl) azo] formamide, 1,1′-azobis (cyclohexane- 1-carbonitrile), 2,2′-azobis (2-methylbutyronitrile), 2,2′-azobis (isobutyronitrile), 2,2′-azobis (2,4-dimethylvaleronitile), 2,2′-azobis (2 methyl-2,4-dimethylvaleritile), Dimethyl 2,2′-azobis (isobutyrate), 2,2′-azobis [2- (2-i idazolin-2-yl) propane], 2,2'-azobis (2-amidopropane) dihydrochloride, 2,2'azobis (N-but-2-methylpropionamide), 2,2'-azobis [N- (2-propen) ) -2-methylpropionamide] and the like.
（分子量の範囲）
本実施形態に係る色材分散剤において用いられる共重合体の分子量の範囲としては、ポリスチレン換算の重量平均分子量で、２，０００〜１００，０００、好ましくは４，０００〜７０，０００、さらに好ましくは６，０００〜３０，０００がより好ましい。
共重合体の重量平均分子量を２，０００以上にすることにより、共重合体の末端に開始剤由来の窒素数が多くなり、かつ立体反発も得られ油溶性染料に対する親和性が良好になり、分散安定性が良い。
共重合体の重量平均分子量が１００，０００以下であると、共重合体の末端に開始剤由来の窒素が存在し、また高分子量化による立体反発が強く起こり、油溶性染料に親和し分散安定化が良好となる。
上記分子量範囲（２，０００〜１００，０００）である場合、本実施形態に係る色材分散剤は、特に構造中に窒素を持つアゾ染料やアゾ顔料に対して有効である。
(Range of molecular weight)
The range of the molecular weight of the copolymer used in the colorant dispersant according to the present embodiment is 2,000 to 100,000, preferably 4,000 to 70,000, more preferably in terms of polystyrene-equivalent weight average molecular weight. Is more preferably 6,000 to 30,000.
By setting the weight average molecular weight of the copolymer to 2,000 or more, the number of nitrogen derived from the initiator at the end of the copolymer is increased, and steric repulsion is also obtained, and the affinity for oil-soluble dyes is improved. Good dispersion stability.
When the weight average molecular weight of the copolymer is 100,000 or less, nitrogen derived from the initiator is present at the end of the copolymer, and steric repulsion due to high molecular weight occurs strongly, making it compatible with oil-soluble dyes and being stable in dispersion. Is improved.
When the molecular weight is in the above range (2,000 to 100,000), the colorant dispersant according to this embodiment is particularly effective for azo dyes and azo pigments having nitrogen in the structure.
（染料の種類と羅列）
本実施形態において用いられる顔料、油溶性染料としては、特に制限はなく、目的に応じて適宜選択することができ、例えば、有機顔料、無機顔料いずれであってもよい。
(Types of dyes and enumeration)
There is no restriction | limiting in particular as a pigment and oil-soluble dye used in this embodiment, According to the objective, it can select suitably, For example, any of an organic pigment and an inorganic pigment may be sufficient.
有機顔料としては、例えば、アゾ顔料、多環式顔料、染料キレート、ニトロ顔料、ニトロソ顔料、アニリンブラック、などが挙げられる。 Examples of organic pigments include azo pigments, polycyclic pigments, dye chelates, nitro pigments, nitroso pigments, and aniline black.
前記アゾ顔料としては、例えば、アゾレーキ、不溶性アゾ顔料、縮合アゾ顔料、キレートアゾ顔料、などが挙げられる。 Examples of the azo pigments include azo lakes, insoluble azo pigments, condensed azo pigments, and chelate azo pigments.
前記多環式顔料としては、例えば、フタロシアニン顔料、ペリレン顔料、ペリノン顔料、アントラキノン顔料、キナクリドン顔料、ジオキサジン顔料、インジゴ顔料、チオインジゴ顔料、イソインドリノン顔料、アンスラキノン顔料、メチン顔料、アリルアミド顔料、キノフタロン顔料、ベンズイミダゾリノン顔料、ペリレン顔料などが挙げられる。 Examples of the polycyclic pigment include phthalocyanine pigment, perylene pigment, perinone pigment, anthraquinone pigment, quinacridone pigment, dioxazine pigment, indigo pigment, thioindigo pigment, isoindolinone pigment, anthraquinone pigment, methine pigment, allylamide pigment, quinophthalone. And pigments, benzimidazolinone pigments, perylene pigments and the like.
前記染料キレートとしては、例えば、塩基性染料型キレート、酸性染料型キレートなどが挙げられる。 Examples of the dye chelate include basic dye chelate and acid dye chelate.
前記無機顔料としては、例えば、酸化チタン、酸化鉄、炭酸カルシウム、硫酸バリウム、水酸化アルミニウム、バリウムイエロー、カドミウムレッド、クロムイエロー、カーボンブラック、などが挙げられる。 Examples of the inorganic pigment include titanium oxide, iron oxide, calcium carbonate, barium sulfate, aluminum hydroxide, barium yellow, cadmium red, chrome yellow, and carbon black.
ブラック系顔料及び油溶性染料として、具体的には、コロンビアン・カーボン社製Ｒａｖｅｎ７６０ｕｌｔｒａ，１０６０ｕｌｔｒａ，１０８０，１１００ｕｌｔｒａ，１１７０，１２００，１２５０，１２５５，１５００，２０００，２５００ｕｌｔｒａ，３５００，５２５０，５７５０，７０００，５０００ｕｌｔｒａＩＩ，１１９０ｕｌｔｒａＩＩ；
キャボット社製ＢｌａｃｋＰｅａｒｌｓＬ、ＭＯＧＵＬ−Ｌ、および、Ｒｅｇａｌ４００Ｒ，６６０Ｒ，３３０Ｒ、ならびに、Ｍｏｎａｒｃｈ８８０，９００，１０００，１３００，１４００；
デグッサ社製ＣｏｌｏｒＢｌａｃｋＦＷ１、ＣｏｌｏｒＢｌａｃｋＦＷ２、ＣｏｌｏｒＢｌａｃｋＦＷ２００、ＣｏｌｏｒＢｌａｃｋ１８、ＣｏｌｏｒＢｌａｃｋＳ１６０、ＣｏｌｏｒＢｌａｃｋＳ１７０、ＳｐｅｃｉａｌＢｌａｃｋ４、ＳｐｅｃｉａｌＢｌａｃｋ４Ａ、ＳｐｅｃｉａｌＢｌａｃｋ６、ＳｐｅｃｉａｌＢｌａｃｋ５５０、およびＰｒｉｎｔｅｘ３５，４５，５５，８５，９５，Ｕ，１４０Ｕ，Ｖ，１４０Ｖ；
三菱化学製Ｎｏ．２５，３３，４０，４５，４７，５５２，９００，９７０，２２００Ｂ，２３００，および２４００Ｂ，ＭＣＦ−８８，ＭＡ６００，ＭＡ７７，ＭＡ８，ＭＡ１００，ＭＡ２３０，およびＭＡ２２０などが挙げられる。
Specific examples of black pigments and oil-soluble dyes include Raven 760 ultra, 1060 ultra, 1080, 1100 ultra, 1170, 1200, 1250, 1255, 1500, 2000, 2500 ultra, 3500, 5250, 5750, 7000, manufactured by Columbian Carbon. 5000ultraII, 1190ultraII;
BlackPearlsL, MOGUL-L, and Regal 400R, 660R, 330R, and Monarch 880, 900, 1000, 1300, 1400 manufactured by Cabot Corporation;
ColorBlack FW1, ColorBlack FW2, ColorBlack FW200, ColorBlack18, ColorBlackS160, ColorBlackS170, SpecialBlack4, 140, Black5, 45, and 45
Mitsubishi Chemical No. 25, 33, 40, 45, 47, 552, 900, 970, 2200B, 2300, and 2400B, MCF-88, MA600, MA77, MA8, MA100, MA230, and MA220.
イエロー系の顔料及び油溶性染料として、具体的には、Ｃ．Ｉ．ピグメントイエロー１，２，３，４，５，６，７，１０，１１，１２，１３，１４，１４Ｃ，１６，１７，２４，３４，３５，３７，４２，５３，５５，６２６５，７３，７４，７５，８１，８３，９３，９５，９７，９８，１００，１０１，１０４，１０８，１０９，１１０，１１４，１１７，１２０，１２８，１２９，１３８，１５０，１５１，１５３，１５４，１５５，１８０；
Ｃ．Ｉ．ソルベントイエロー１，２，３，１３，１４，１９，２１，２２，２９，３６，３７，３８，３９，４０，４２，４３，４４，４５，４７，６２，６３，７１，７４，７６，７９，８１，８２，８３：１，８５，８６，８８，１５１；
Ｃ．Ｉ．ディスパースイエロー３，７，８，２３，３９，５１，５４，６０，７１，８６，１１４，１６３などが挙げられる。
Specific examples of yellow pigments and oil-soluble dyes include C.I. I. Pigment Yellow 1, 2, 3, 4, 5, 6, 7, 10, 11, 12, 13, 14, 14C, 16, 17, 24, 34, 35, 37, 42, 53, 55, 6265, 73, 74,75,81,83,93,95,97,98,100,101,104,108,109,110,114,117,120,128,129,138,150,151,153,154,155 180;
C. I. Solvent Yellow 1, 2, 3, 13, 14, 19, 21, 22, 29, 36, 37, 38, 39, 40, 42, 43, 44, 45, 47, 62, 63, 71, 74, 76, 79, 81, 82, 83: 1, 85, 86, 88, 151;
C. I. Disperse Yellow 3, 7, 8, 23, 39, 51, 54, 60, 71, 86, 114, 163 and the like.
マゼンタ系の顔料及び油溶性染料として、具体的には、Ｃ．Ｉ．ピグメントレッド１，２，３，４，５，６，７，８，９，１０，１１，１２，１３，１４，１５，１６，１７，１８，１９，２１，２２，２３，３０，３１，３２，３７，３８，３９，４０，４８（Ｃａ），４８（Ｍｎ），４８：２，４８：３，４８：４，４９，４９：１，５０，５１，５２，５２：２，５３：１，５３，５５，５７（Ｃａ），５７：１，６０，６０：１，６３：１，６３：２，６４，６４：１，８１，８３，８７，８８，８９，９０，１０１（べんがら），１０４，１０５，１０６，１０８（カドミウムレッド），１１２，１１４，１２２（キナクリドンマゼンタ），１２３，１４６，１４９，１６３，１６６，１６８，１７０，１７２，１７７，１７８，１７９，１８４，１８５，１９０，１９３，２０２，２０９，２１９，２６９など；
Ｃ．Ｉ．ソルベントレッド８，２７，３５，３６，３７，３８，３９，４０，４９，５８，６０，６５，６９，８１，８３：１，８６，８９，９１，９２，９７，９９，１００，１０９，１１８，１１９，１２２，１２７，２１８；
Ｃ．Ｉ．ピグメントバイオレット１９；
Ｃ．Ｉ．ディスパースレッド１，１１，１５，５０，５３，５５，５５：１，５９，６０，６５，７０，７４，７５，９１，９２，９３，１４５，１４６，１５２，１５４，１５８，１７９，１９０，１９０：１，１９１，２０７，２３９，２４０，３０２，３４３；
Ｃ．Ｉ．ディスパースバットレッド４１；
Ｃ．Ｉ．ディスパースバイオレット８，１７，２３，２７，２８，２９，３６，５７などが挙げられる。
Specific examples of magenta pigments and oil-soluble dyes include C.I. I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 21, 22, 23, 30, 31, 32, 37, 38, 39, 40, 48 (Ca), 48 (Mn), 48: 2, 48: 3, 48: 4, 49, 49: 1, 50, 51, 52, 52: 2, 53: 1, 53, 55, 57 (Ca), 57: 1, 60, 60: 1, 63: 1, 63: 2, 64, 64: 1, 81, 83, 87, 88, 89, 90, 101 (Bengara) ), 104, 105, 106, 108 (cadmium red), 112, 114, 122 (quinacridone magenta), 123, 146, 149, 163, 166, 168, 170, 172, 177, 178, 179, 184, 185 190, 193, 202, 209, 2 Such as 9,269;
C. I. Solvent Red 8, 27, 35, 36, 37, 38, 39, 40, 49, 58, 60, 65, 69, 81, 83: 1, 86, 89, 91, 92, 97, 99, 100, 109, 118, 119, 122, 127, 218;
C. I. Pigment violet 19;
C. I. Disperse thread 1, 11, 15, 50, 53, 55, 55: 1, 59, 60, 65, 70, 74, 75, 91, 92, 93, 145, 146, 152, 154, 158, 179, 190, 190: 1, 191, 207, 239, 240, 302, 343;
C. I. Disperse Bat Red 41;
C. I. Disperse violet 8, 17, 23, 27, 28, 29, 36, 57 etc. are mentioned.
シアン系の顔料及び油溶性染料として、具体的には、Ｃ．Ｉ．ピグメントブルー１，２，３，１５，１５：１，１５：２，１５：３，１５：３４，１６，１７：１，２２，２５，５６，６０，６６；
Ｃ．Ｉ．ソルベントブルー１１，１４，２４，２５，２６，３４，３６，３７，３８，３９，４２，４３，４４，４５，４８，５２，５３，５５，５９，６３，６７，７０，８３，１０５，１１１；
Ｃ．Ｉ．ディスパースブルー１９，２６，２６：１，３５，５５，５６，５８，６０，６４，６４：１，７２，７２：１，８１，８１：１，９１，９５，１０８，１３１，１４１，１４５，１６５，３５９；
Ｃ．Ｉ．バットブルー４，６０，６３などが挙げられる。
Specific examples of cyan pigments and oil-soluble dyes include C.I. I. Pigment Blue 1, 2, 3, 15, 15: 1, 15: 2, 15: 3, 15:34, 16, 17: 1, 22, 25, 56, 60, 66;
C. I. Solvent Blue 11, 14, 24, 25, 26, 34, 36, 37, 38, 39, 42, 43, 44, 45, 48, 52, 53, 55, 59, 63, 67, 70, 83, 105, 111;
C. I. Disperse Blue 19, 26, 26: 1, 35, 55, 56, 58, 60, 64, 64: 1, 72, 72: 1, 81, 81: 1, 91, 95, 108, 131, 141, 145 , 165, 359;
C. I. Bat blue 4, 60, 63 and the like.
その他の油溶性染料としては、具体的に、Ｃ．Ｉ．ディスパースオレンジ１，１：１，５，２０，２５，２５：１，３０，３２，３３，４７，５６，７６；
Ｃ．Ｉ．ディスパースブラウン２などが挙げられる。
Specific examples of other oil-soluble dyes include C.I. I. Disperse orange 1, 1: 1, 5, 20, 25, 25: 1, 30, 32, 33, 47, 56, 76;
C. I. Disperse Brown 2 etc. are mentioned.
上記顔料及び油溶性染料は、単独で使用しても良く、また上記した各群内もしくは各群間より複数種選択してこれらを組み合わせて使用してもよい。 The above-mentioned pigments and oil-soluble dyes may be used alone, or a plurality of these pigments and oil-soluble dyes may be selected from each group or between each group and used in combination.
（分散機）
本発明の水性色材分散液を製造するために使用する分散機は特に限定されないが、例えば、横型サンドミル、縦型サンドミル、アニュラー型ビーズミル、アトライター、マイクロフルイタイザー、ハイスピードミキサー、ホモミキサー、ホモジナイザー、ボールミル、ペイントシェーカー、ロールミル、石臼式ミル、超音波分散機等が挙げられ、分散体を製造するために通常に使用されるあらゆる分散機や混合機を使用することができる。
(Dispersing machine)
The disperser used for producing the aqueous color material dispersion of the present invention is not particularly limited. For example, a horizontal sand mill, a vertical sand mill, an annular bead mill, an attritor, a microfluidizer, a high speed mixer, a homomixer, A homogenizer, a ball mill, a paint shaker, a roll mill, a stone mill, an ultrasonic disperser and the like can be mentioned, and any disperser or mixer which is usually used for producing a dispersion can be used.
（水）
本実施形態で使用する水は顔料の分散媒である。水としては、イオン交換水、限外濾過水、逆浸透水、蒸留水等の純水、または超純水を用いることができる。
水は単独で使用してもよいし、水と水溶性溶剤からなる混合溶媒でもよい。
(water)
The water used in this embodiment is a pigment dispersion medium. As the water, pure water such as ion exchange water, ultrafiltration water, reverse osmosis water, distilled water, or ultrapure water can be used.
Water may be used alone or a mixed solvent composed of water and a water-soluble solvent.
（安定剤、乾燥防止剤）
アセトン、メチルエチルケトン、メチルブチルケトン、メチルイソブチルケトン、等のケトン類；メタノール、エタノール、１−プロパノール、２−プロパノール、２−メチル−１−プロパノール、１−ブタノール、２−メトキシエタノール、等のアルコール類；テトラヒドロフラン、１，４−ジオキサン、１，２−ジメトキシエタン、等のエーテル類；ジメチルホルムアミド、Ｎ’−メチルピロリドン，エチレングリコール，ジエチレングリコール，トリエチレングリコール、テトラエチレングリコール、プロピレングリコール、ポリエチレングリコール、ポリプロピレングリコールなどのグリコール類；ブタンジオール、ペンタンジオール、ヘキサンジオール、およびこれらと同族のジオールなどのジオール類；ラウリン酸プロピレングリコールなどのグリコールエステル；ジエチレングリコールモノエチル、ジエチレングリコールモノブチル、ジエチレングリコールモノヘキシルの各エーテル、プロピレングリコールエーテル、ジプロピレングリコールエーテル、およびトリエチレングリコールエーテルを含むセロソルブなどのグリコールエーテル類；あるいは、スルホラン；γ−ブチロラクトンなどのラクトン類；Ｎ−（２−ヒドロキシエチル）ピロリドンなどのラクタム類；グリセリンおよびその誘導体など、水溶性有機溶剤として知られる他の各種の溶剤などを挙げることができる。
(Stabilizer, anti-drying agent)
Ketones such as acetone, methyl ethyl ketone, methyl butyl ketone and methyl isobutyl ketone; alcohols such as methanol, ethanol, 1-propanol, 2-propanol, 2-methyl-1-propanol, 1-butanol and 2-methoxyethanol Ethers such as tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane; dimethylformamide, N′-methylpyrrolidone, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, polyethylene glycol, polypropylene Glycols such as glycol; diols such as butanediol, pentanediol, hexanediol, and diols of the same family; propylene glycol laurate Glycol esters such as coal; glycol ethers such as cellosolve including diethylene glycol monoethyl, diethylene glycol monobutyl, diethylene glycol monohexyl ether, propylene glycol ether, dipropylene glycol ether, and triethylene glycol ether; or sulfolane; γ- Examples include lactones such as butyrolactone; lactams such as N- (2-hydroxyethyl) pyrrolidone; various other solvents known as water-soluble organic solvents such as glycerin and derivatives thereof.
これらの水溶性有機溶剤は１種または２種以上混合して用いることができる。
またこのとき使用する水溶性有機溶剤は、後工程で脱溶剤等の必要がないことから、高沸点の水溶性有機溶剤が好ましい。
These water-soluble organic solvents can be used alone or in combination.
In addition, the water-soluble organic solvent used at this time is preferably a high-boiling water-soluble organic solvent because it is not necessary to remove the solvent in a subsequent step.
このような高沸点の水溶性有機溶剤としては、例えば、エチレングリコール、ジエチレングリコール、トリエチレングリコール、テトラエチレングリコール、プロピレングリコール、ポリエチレングリコール、ポリプロピレングリコールなどのグリコール類；ブタンジオール、ペンタンジオール、ヘキサンジオール、およびこれらと同族のジオールなどのジオール類；ラウリン酸プロピレングリコールなどのグリコールエステル；ジエチレングリコールモノエチル、ジエチレングリコールモノブチル、ジエチレングリコールモノヘキシルの各エーテル、プロピレングリコールエーテル、ジプロピレングリコールエーテル、およびトリエチレングリコールエーテルを含むセロソルブなどのグリコールエーテル類；スルホラン；γ−ブチロラクトンなどのラクトン類；Ｎ−（２−ヒドロキシエチル）ピロリドンなどのラクタム類；グリセリンおよびその誘導体など水溶性有機溶剤として知られる他の各種の溶剤などを挙げることができる。
これらの水溶性有機溶剤は１種または２種以上混合して用いることができる。
Examples of such high-boiling water-soluble organic solvents include glycols such as ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, polyethylene glycol, and polypropylene glycol; butanediol, pentanediol, hexanediol, And diols such as diols of the same family; glycol esters such as propylene glycol laurate; ethers of diethylene glycol monoethyl, diethylene glycol monobutyl, diethylene glycol monohexyl, propylene glycol ether, dipropylene glycol ether, and triethylene glycol ether Containing glycol ethers such as cellosolve; sulfolane; γ-butyrolacto Lactones such as; N-(2-hydroxyethyl) lactams, such as pyrrolidone; and other various solvents known as glycerol and water-soluble organic solvents such as its derivatives.
These water-soluble organic solvents can be used alone or in combination.
なお、前記工程で使用する水溶性有機溶剤には、例えば安定性や乾燥防止剤としての機能を果たすものがある。 In addition, some water-soluble organic solvents used at the said process fulfill | perform the function as stability or a drying inhibitor, for example.
（界面活性剤）
前記界面活性剤は、表面張力等のインク特性を調整するために添加する。このために添加することのできる界面活性剤は特に限定されるものではなく、各種のアニオン性界面活性剤、カチオン性界面活性剤、両性界面活性剤などが挙げられ、これらの中では、アニオン性界面活性剤、ノニオン性界面活性剤が好ましい。
(Surfactant)
The surfactant is added to adjust ink properties such as surface tension. The surfactant that can be added for this purpose is not particularly limited, and examples include various anionic surfactants, cationic surfactants, and amphoteric surfactants. Among these, anionic Surfactants and nonionic surfactants are preferred.
アニオン性界面活性剤としては、例えば、アルキルベンゼンスルホン酸塩、アルキルフェニルスルホン酸塩、アルキルナフタレンスルホン酸塩、高級脂肪酸塩、高級脂肪酸エステルの硫酸エステル塩、高級脂肪酸エステルのスルホン酸塩、高級アルコールエーテルの硫酸エステル塩及びスルホン酸塩、高級アルキルスルホコハク酸塩、ポリオキシエチレンアルキルエーテルカルボン酸塩、ポリオキシエチレンアルキルエーテル硫酸塩、アルキルリン酸塩、ポリオキシエチレンアルキルエーテルリン酸塩等が挙げられる。これらの具体例として、ドデシルベンゼンスルホン酸塩、イソプロピルナフタレンスルホン酸塩、モノブチルフェニルフェノールモノスルホン酸塩、モノブチルビフェニルスルホン酸塩、ジブチルフェニルフェノールジスルホン酸塩、などを挙げることができる。 Examples of the anionic surfactant include alkylbenzene sulfonate, alkylphenyl sulfonate, alkylnaphthalene sulfonate, higher fatty acid salt, sulfate of higher fatty acid ester, sulfonate of higher fatty acid ester, higher alcohol ether. And sulfates and sulfonates thereof, higher alkyl sulfosuccinates, polyoxyethylene alkyl ether carboxylates, polyoxyethylene alkyl ether sulfates, alkyl phosphates, polyoxyethylene alkyl ether phosphates, and the like. Specific examples thereof include dodecylbenzenesulfonate, isopropylnaphthalenesulfonate, monobutylphenylphenol monosulfonate, monobutylbiphenylsulfonate, dibutylphenylphenol disulfonate, and the like.
ノニオン性界面活性剤としては、例えば、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキルフェニルエーテル、ポリオキシエチレン脂肪酸エステル、ソルビタン脂肪酸エステル、ポリオキシエチレンソルビタン脂肪酸エステル、ポリオキシエチレンソルビトール脂肪酸エステル、グリセリン脂肪酸エステル、ンソルビトール脂肪酸エステル、グリセリン脂肪酸エステル、ポリオキシエチレングリセリン脂肪酸エステル、ポリグリセリン脂肪酸エステル、ショ糖脂肪酸エステル、ポリオキシエチレンアルキルアミン、ポリオキシエチレン脂肪酸アミド、脂肪酸アルキロールアミド、アルキルアルカノールアミド、アセチレングリコール、アセチレングリコールのオキシエチレン付加物、ポリエチレングリコールポリプロピレングリコールブロックコポリマー等を挙げることができる。これらの中では、ポリオキシエチレンノニルフェニルエーテル、ポリオキシエチレンオクチルフェニルエーテル、ポリオキシエチレンドデシルフェニルエーテル、ポリオキシエチレンアルキルエーテル、ポリオキシエチレン脂肪酸エステル、ソルビタン脂肪酸エステル、ポリオキシエチレンソルビタン脂肪酸エステル、脂肪酸アルキロールアミド、アセチレングリコール、アセチレングリコールのオキシエチレン付加物、ポリエチレングリコールポリプロピレングリコールブロックコポリマーが好ましい。 Nonionic surfactants include, for example, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbitol fatty acid ester, glycerin fatty acid ester , Sorbitol fatty acid ester, glycerin fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyglycerin fatty acid ester, sucrose fatty acid ester, polyoxyethylene alkylamine, polyoxyethylene fatty acid amide, fatty acid alkylolamide, alkyl alkanolamide, acetylene glycol , Oxyethylene adduct of acetylene glycol, polyethylene glycol polypropylene It can be exemplified glycol block copolymer or the like. Among these, polyoxyethylene nonyl phenyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene dodecyl phenyl ether, polyoxyethylene alkyl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, fatty acid Preference is given to alkylolamide, acetylene glycol, oxyethylene adducts of acetylene glycol and polyethylene glycol polypropylene glycol block copolymers.
その他の界面活性剤として、ポリシロキサンオキシエチレン付加物のようなシリコーン系界面活性剤；パーフルオロアルキルカルボン酸塩、パーフルオロアルキルスルホン酸塩、オキシエチレンパーフルオロアルキルエーテルのようなフッ素系界面活性剤；スピクリスポール酸、ラムノリピド、リゾレシチンのようなバイオサーファクタント等も使用することができる。 Other surfactants include silicone surfactants such as polysiloxane oxyethylene adducts; fluorine surfactants such as perfluoroalkyl carboxylates, perfluoroalkyl sulfonates, and oxyethylene perfluoroalkyl ethers. Biosurfactants such as spicrispolic acid, rhamnolipid, lysolecithin and the like can also be used.
これらの界面活性剤は、単独で用いることもでき、又２種類以上を混合して用いることもできる。界面活性剤を添加する場合その添加量はインキの全質量に対し、０．００１〜２質量％の範囲が好ましく、０．００１〜１．５質量％であることがより好ましく、０．０１〜１質量％の範囲であることがさらに好ましい。界面活性剤の添加量が０．００１質量％未満の場合は、界面活性剤添加の効果が得られない傾向にあり、２質量％を超えて用いると、インキが滲むなどの問題を生じやすくなる。 These surfactants can be used alone or in combination of two or more. When the surfactant is added, the addition amount is preferably in the range of 0.001 to 2% by mass, more preferably 0.001 to 1.5% by mass, relative to the total mass of the ink, and 0.01 to More preferably, it is in the range of 1% by mass. When the added amount of the surfactant is less than 0.001% by mass, the effect of adding the surfactant tends to be not obtained, and when it exceeds 2% by mass, problems such as ink bleeding tend to occur. .
また、必要に応じて防腐剤、粘度調整剤、ｐＨ調整剤、キレート化剤、可塑剤、酸化防止剤、紫外線吸収剤等を添加することができる。 Moreover, antiseptic | preservative, a viscosity modifier, a pH adjuster, a chelating agent, a plasticizer, antioxidant, an ultraviolet absorber etc. can be added as needed.
（防腐剤）
例えば、日本曹達製ベストサイド３００、５００、６００など、有機硫黄系、有機窒素硫黄系、有機ハロゲン系、ハロアリルスルホン系、ヨードプロパギル系、Ｎ−ハロアルキルチオ系、ベンゾチアゾール系、二トリル系、ピリジン系、８−オキシキノリン系、イソチアゾリン系、ジチオール系、ピリジンオキシド系、ニトロプロパン系、有機スズ系、フェノール系、第４アンモニウム塩系、トリアジン系、チアジアジン系、アニリド系、アダマンタン系、ジチオカーバメイト系、ブロム化インダノン系、ベンジルプロムアセテート系、無機塩系などの化合物が挙げられる。
(Preservative)
For example, Nippon Soda Best Side 300, 500, 600, etc., organic sulfur, organic nitrogen sulfur, organic halogen, haloallylsulfone, iodopropargyl, N-haloalkylthio, benzothiazole, nitrile , Pyridine, 8-oxyquinoline, isothiazoline, dithiol, pyridine oxide, nitropropane, organotin, phenol, quaternary ammonium salt, triazine, thiadiazine, anilide, adamantane, dithio Examples thereof include carbamate compounds, brominated indanone compounds, benzylprom acetate compounds, and inorganic salt compounds.
例えばイソチアゾリン系化合物としては、１−ベンズイソチアゾリン−３−オンのアミン塩、１，２−ベンズイソチアゾリン−３−オン、２−ｎ−オクチル−４−イソチアゾリン−３−オン、５−クロロ−２−メチル−４−イソチアゾリン−３−オン、５−クロロ−２−メチル−４−イソチアゾリン−３−オンマグネシウムクロライド、５−クロロ−２−メチル−４−イソチアゾリン−３−オンカルシウムクロライド、２−メチル−４−イソチアゾリン−３−オンカルシウムクロライド、２−メチル−４−イソチアゾリン−３−オンカルシウムクロライド等が挙げられる。 For example, as an isothiazoline-based compound, an amine salt of 1-benzisothiazolin-3-one, 1,2-benzisothiazolin-3-one, 2-n-octyl-4-isothiazolin-3-one, 5-chloro-2- Methyl-4-isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one magnesium chloride, 5-chloro-2-methyl-4-isothiazolin-3-one calcium chloride, 2-methyl- Examples include 4-isothiazolin-3-one calcium chloride and 2-methyl-4-isothiazolin-3-one calcium chloride.
その他、デヒドロ酢酸ナトリウム、ソルビン酸ナトリウム、安息香酸ナトリウムなどが挙げられる。 Other examples include sodium dehydroacetate, sodium sorbate, and sodium benzoate.
以下、実施例によって上記した効果についてより具体的に説明するが、本発明は以下の記載によって限定されない。 Hereinafter, although an effect mentioned above is explained more concretely by an example, the present invention is not limited by the following statements.
（色材分散樹脂製造例）
＜製造例１＞
フラスコに、あらかじめスチレン（Ｓｔ） ３５部、メタクリル酸１５部、２，２’−アゾビス（２−メチルブチロニトリル）８部、メチルエチルケトンを２３３部仕込み、窒素を供給し１０分間バブリングを行い、系中を脱気した。
フラスコ内が８０℃になるよう加温し、フラスコ内温 ８０℃に維持しながら、スチレン３５部、メタクリル酸１５部を２時間かけて滴下し、滴下終了後２０時間反応を行い、固化、解砕工程を経て、樹脂粉体を得た。重合率約１００％の樹脂粉体が得られた。
製造例１の重量平均分子量（Ｍｗ）は９５００であった。
(Color material dispersion resin production example)
<Production Example 1>
Into the flask, 35 parts of styrene (St), 15 parts of methacrylic acid, 8 parts of 2,2′-azobis (2-methylbutyronitrile) and 233 parts of methyl ethyl ketone are charged, nitrogen is supplied, and bubbling is performed for 10 minutes. I was degassed inside.
The flask was heated to 80 ° C., and while maintaining the flask internal temperature at 80 ° C., 35 parts of styrene and 15 parts of methacrylic acid were added dropwise over 2 hours. A resin powder was obtained through a crushing process. A resin powder having a polymerization rate of about 100% was obtained.
The weight average molecular weight (Mw) of Production Example 1 was 9,500.
＜製造例２＞
製造例１の２，２’−アゾビス（２−メチルブチロニトリル）を２，２’−アゾビス（イソブチロニトリル）に変えた以外は同様の操作を行った。重合率約１００％の樹脂粉体が得られた。
製造例２の重量平均分子量（Ｍｗ）は９０００であった。
<Production Example 2>
The same operation was performed except that 2,2′-azobis (2-methylbutyronitrile) in Production Example 1 was changed to 2,2′-azobis (isobutyronitrile). A resin powder having a polymerization rate of about 100% was obtained.
The weight average molecular weight (Mw) of Production Example 2 was 9000.
＜製造例３＞
製造例１の２，２’−アゾビス（２−メチルブチロニトリル）を２，２’−アゾビス（２，４−ジメチルバレロニトリル）に変えた以外は、製造例１と同様の操作を行った。重合率約１００％の樹脂粉体が得られた。
製造例２の重量平均分子量（Ｍｗ）は、８０００であった。
<Production Example 3>
The same operation as in Production Example 1 was performed except that 2,2′-azobis (2-methylbutyronitrile) in Production Example 1 was changed to 2,2′-azobis (2,4-dimethylvaleronitrile). . A resin powder having a polymerization rate of about 100% was obtained.
The weight average molecular weight (Mw) of Production Example 2 was 8,000.
＜製造例４＞
製造例１の２，２’−アゾビス（２−メチルブチロニトリル）を１，１’−アゾビス（シクロヘキサン−１−カルボニトリル）に変えた以外は、製造例１と同様の操作を行った。重合率約１００％の樹脂粉体が得られた。
製造例４の重量平均分子量（Ｍｗ）は、１００００であった。
<Production Example 4>
The same operation as in Production Example 1 was performed, except that 2,2′-azobis (2-methylbutyronitrile) in Production Example 1 was changed to 1,1′-azobis (cyclohexane-1-carbonitrile). A resin powder having a polymerization rate of about 100% was obtained.
The weight average molecular weight (Mw) of Production Example 4 was 10,000.
＜製造例５＞
フラスコに、あらかじめスチレン（Ｓｔ）５部、メタクリル酸２５部、アクリル酸２−エチルヘキシル２０部、２，２’−アゾビス（２−メチルブチロニトリル）８部、メチルエチルケトンを２３３部仕込み、窒素を供給し１０分間バブリングを行い、系中を脱気した。
フラスコ内が８０℃になるよう加温し、フラスコ内温 ８０℃に維持しながら、スチレン５部、メタクリル酸２５部、アクリル酸２−エチルヘキシル２０部、を２時間かけて滴下し、滴下終了後２０時間反応を行い、固化、解砕工程を経て、樹脂粉体を得た。重合率約１００％の樹脂粉体が得られた。
製造例５の重量平均分子量（Ｍｗ）は、９５００であった。
<Production Example 5>
In a flask, 5 parts of styrene (St), 25 parts of methacrylic acid, 20 parts of 2-ethylhexyl acrylate, 8 parts of 2,2′-azobis (2-methylbutyronitrile) and 233 parts of methyl ethyl ketone are charged in advance and nitrogen is supplied. Then, bubbling was performed for 10 minutes to degas the system.
While the flask was heated to 80 ° C. and maintained at 80 ° C., 5 parts of styrene, 25 parts of methacrylic acid, and 20 parts of 2-ethylhexyl acrylate were added dropwise over 2 hours. Reaction was performed for 20 hours, and resin powder was obtained through solidification and crushing steps. A resin powder having a polymerization rate of about 100% was obtained.
The weight average molecular weight (Mw) of Production Example 5 was 9500.
＜製造例６＞
フラスコに、あらかじめスチレン（Ｓｔ）１５部、メタクリル酸２０部、アクリル酸ブチル１５部、２，２’−アゾビス（２−メチルブチロニトリル）８部、メチルエチルケトンを２３３部仕込み、窒素を供給し１０分間バブリングを行い、系中を脱気した。
フラスコ内が８０℃になるよう加温し、フラスコ内温８０℃に維持しながら、スチレン１５部、メタクリル酸２０部、アクリル酸ブチル１５部、を２時間かけて滴下し、滴下終了後２０時間反応を行い、固化、解砕工程を経て、樹脂粉体を得た。重合率約１００％の樹脂粉体が得られた。
製造例６の重量平均分子量（Ｍｗ）は、９５００であった。
<Production Example 6>
A flask is charged with 15 parts of styrene (St), 20 parts of methacrylic acid, 15 parts of butyl acrylate, 8 parts of 2,2′-azobis (2-methylbutyronitrile) and 233 parts of methyl ethyl ketone, and nitrogen is supplied to the flask. Bubbling was performed for a minute, and the system was deaerated.
While the flask was heated to 80 ° C. and maintained at 80 ° C., 15 parts of styrene, 20 parts of methacrylic acid and 15 parts of butyl acrylate were added dropwise over 2 hours, and 20 hours after the completion of the addition. Reaction was performed, and resin powder was obtained through solidification and crushing steps. A resin powder having a polymerization rate of about 100% was obtained.
The weight average molecular weight (Mw) of Production Example 6 was 9500.
＜製造例７＞
製造例１の２，２’−アゾビス（２−メチルブチロニトリル）をジメチル２，２’−アゾビス（イソブチレート）に変えた以外は、製造例１と同様の操作を行った。重合率約１００％の樹脂粉体が得られた。
製造例７の重量平均分子量（Ｍｗ）は９４００であった。
<Production Example 7>
The same operation as in Production Example 1 was performed except that 2,2′-azobis (2-methylbutyronitrile) in Production Example 1 was changed to dimethyl 2,2′-azobis (isobutyrate). A resin powder having a polymerization rate of about 100% was obtained.
The weight average molecular weight (Mw) of Production Example 7 was 9400.
＜製造例８＞
製造例１の２，２’−アゾビス（２−メチルブチロニトリル）を２，２’−アゾビス（２−アミジノプロパン）ジヒドロクロライドに変えた以外は、製造例１と同様の操作を行った。重合率約１００％の樹脂粉体が得られた。
製造例８の重量平均分子量（Ｍｗ）は８２００であった。
<Production Example 8>
The same operation as in Production Example 1 was carried out except that 2,2′-azobis (2-methylbutyronitrile) in Production Example 1 was changed to 2,2′-azobis (2-amidinopropane) dihydrochloride. A resin powder having a polymerization rate of about 100% was obtained.
The weight average molecular weight (Mw) of Production Example 8 was 8200.
＜製造例９＞
フラスコに、あらかじめスチレン（Ｓｔ） ３５部、メタクリル酸１５部、２，２’−アゾビス（２−メチルブチロニトリル）３部、メチルエチルケトンを２３３部仕込み、窒素を供給し１０分間バブリングを行い、系中を脱気した。
フラスコ内が８０℃になるよう加温し、フラスコ内温 ８０℃に維持しながら、スチレン３５部、メタクリル酸１５部を２時間かけて滴下し、滴下終了後２０時間反応を行い、固化、解砕工程を経て、樹脂粉体を得た。重合率約１００％の樹脂粉体が得られた。
製造例９の重量平均分子量（Ｍｗ）は３００００であった。
<Production Example 9>
A flask is charged with 35 parts of styrene (St), 15 parts of methacrylic acid, 3 parts of 2,2′-azobis (2-methylbutyronitrile) and 233 parts of methyl ethyl ketone, nitrogen is supplied, and bubbling is performed for 10 minutes. I was degassed inside.
The flask was heated to 80 ° C., and while maintaining the flask internal temperature at 80 ° C., 35 parts of styrene and 15 parts of methacrylic acid were added dropwise over 2 hours. A resin powder was obtained through a crushing process. A resin powder having a polymerization rate of about 100% was obtained.
The weight average molecular weight (Mw) of Production Example 9 was 30000.
＜製造例１０＞
製造例１の２，２’‐アゾビス（２−メチルブチロニトリル）を４，４’‐アゾビス（４シアノペンタノイックアシッド）に変えた以外は、製造例１と同様の操作を行った結果、重合率約１００％の樹脂粉体が得られた。
製造例１０の重量平均分子量（Ｍｗ）は９５００であった。
<Production Example 10>
Results of performing the same operations as in Production Example 1 except that 2,2′-azobis (2-methylbutyronitrile) in Production Example 1 was changed to 4,4′-azobis (4 cyanopentanoic acid) A resin powder having a polymerization rate of about 100% was obtained.
The weight average molecular weight (Mw) of Production Example 10 was 9500.
＜比較製造例１＞
製造例１の２，２’−アゾビス（２−メチルブチロニトリル）を過酸化ベンゾイルに変えた以外は、製造例１と同様の操作を行った。重合率約１００％の樹脂粉体となった。
比較製造例１の重量平均分子量（Ｍｗ）は、９０００であった。
<Comparative Production Example 1>
The same operation as in Production Example 1 was performed except that 2,2′-azobis (2-methylbutyronitrile) in Production Example 1 was changed to benzoyl peroxide. A resin powder having a polymerization rate of about 100% was obtained.
The weight average molecular weight (Mw) of Comparative Production Example 1 was 9000.
＜比較製造例２＞
製造例１の２，２’−アゾビス（２−メチルブチロニトリル）をターシャリーブチルパーオキシ２エチルヘキサノエートに変えた以外は、製造例１と同様の操作を行った。重合率約１００％の樹脂粉体となった。
比較製造例２の重量平均分子量（Ｍｗ）は、９５００であった。
<Comparative Production Example 2>
The same operation as in Production Example 1 was carried out except that 2,2′-azobis (2-methylbutyronitrile) in Production Example 1 was changed to tertiary butyl peroxy 2-ethylhexanoate. A resin powder having a polymerization rate of about 100% was obtained.
The weight average molecular weight (Mw) of Comparative Production Example 2 was 9,500.
（保存安定性評価）
＜色材分散樹脂水溶液の作製＞
フラスコに、上記製造例または比較製造例により得られた色材分散樹脂、苛性カリ（水酸化カリウム）、純水を、以下の表１に示す組成にて混合し、７０℃３時間撹拌することにより、２５％の色材分散樹脂水溶液が得られた。
(Storage stability evaluation)
<Preparation of aqueous solution of colorant dispersed resin>
By mixing the colorant-dispersed resin, caustic potash (potassium hydroxide) and pure water obtained in the above production example or comparative production example with the composition shown in Table 1 below, and stirring at 70 ° C. for 3 hours. 25% of a colorant-dispersed resin aqueous solution was obtained.
＜水性色材分散液の組成＞
以下の表２に示すように、＜色材分散樹脂水溶液の作製＞の項で得られた色材分散樹脂水溶液と各成分とを、０．２ｍｍ径ガラスビーズ２００ｇとともに配合し、ダイノーミル（シンマルエンタープライゼス製）により３，０００ｒｐｍ １０時間分散処理を行った。
<Composition of aqueous coloring material dispersion>
As shown in Table 2 below, the colorant-dispersed resin aqueous solution obtained in the section <Preparation of colorant-dispersed resin aqueous solution> and each component are blended together with 200 g of 0.2 mm-diameter glass beads, Dispersion treatment was performed at 3,000 rpm for 10 hours using an enterprise.
＜水溶性インキ組成＞
以下の表３に示すように、＜水性色材分散液の組成＞の項で得られた水性色材分散液と表３に記した材料とを混合し、１時間撹拌することで、以下に示す実施例および比較例に係るインキ組成物を得た。
なお、実施例および比較例に係るインキ組成物は、調製時に、ろ紙（Ｎｏ５ＣＡＤＶＡＮＴＥＣ社製）にて吸引ろ過し粗大粒子などを除いた。
<Water-soluble ink composition>
As shown in Table 3 below, the aqueous color material dispersion obtained in the section <Composition of the aqueous color material dispersion> and the materials described in Table 3 were mixed and stirred for 1 hour. Ink compositions according to the examples and comparative examples shown were obtained.
In addition, the ink composition which concerns on an Example and a comparative example was suction-filtered with the filter paper (made by No5CADVANTEC) at the time of preparation, and removed the coarse particle.
また、実施例および比較例に係るインキ組成物の評価結果を表４〜６に示す。 Moreover, the evaluation result of the ink composition which concerns on an Example and a comparative example is shown to Tables 4-6.
インキ組成物の評価には、インキ作成直後、保存安定性試験後における粒子径測定を行った。
粒子径測定においては、動的光散乱法粒子測定装置（大塚電子製 ＦＰＡＲ−１０００）により平均粒子径を測定した。
表４〜６中の数値の単位は、平均粒子径（ｎｍ）である。
For the evaluation of the ink composition, the particle size was measured immediately after the ink preparation and after the storage stability test.
In the particle diameter measurement, the average particle diameter was measured with a dynamic light scattering particle measuring apparatus (FPAR-1000 manufactured by Otsuka Electronics Co., Ltd.).
The unit of the numerical values in Tables 4 to 6 is the average particle diameter (nm).
なお、保存安定性試験とは、６０℃７日間静置によるインク組成物の保存安定性評価のことを示す。
６０℃７日間静置による保存安定性試験におけるインク組成物の保存安定性評価基準は以下に示す通りである。
The storage stability test refers to evaluation of storage stability of the ink composition by standing at 60 ° C. for 7 days.
The storage stability evaluation criteria of the ink composition in the storage stability test by standing at 60 ° C. for 7 days are as follows.
＜保存安定性評価基準＞
Ａ：（保存安定性試験後の平均粒子径−インキ作製直後の平均粒子径）／（保存安定性試験後の平均粒子径）×１００％において、５％未満であった。
Ｂ：（保存安定性試験後の平均粒子径−インキ作製直後の平均粒子径）／（保存安定性試験後の平均粒子径）×１００％において、５％以上８％未満であった。
Ｃ：（保存安定性試験後の平均粒子径−インキ作製直後の平均粒子径）／（保存安定性試験後の平均粒子径）×１００％において、８％以上１５％未満であった。
Ｄ：（保存安定性試験後の平均粒子径−インキ作製直後の平均粒子径）／（保存安定性試験後の平均粒子径）×１００％において、１５％以上であった。
評価基準Ｂ以上で、保存安定性に優れていると判定される。
<Storage stability evaluation criteria>
A: (Average particle diameter after storage stability test−Average particle diameter immediately after ink preparation) / (Average particle diameter after storage stability test) × 100% was less than 5%.
B: (average particle diameter after storage stability test−average particle diameter immediately after ink preparation) / (average particle diameter after storage stability test) × 100% was 5% or more and less than 8%.
C: (average particle diameter after storage stability test−average particle diameter immediately after ink preparation) / (average particle diameter after storage stability test) × 100% was 8% or more and less than 15%.
D: (average particle diameter after storage stability test−average particle diameter immediately after ink preparation) / (average particle diameter after storage stability test) × 100% was 15% or more.
It is determined that the storage stability is excellent when the evaluation standard is B or higher.
表４中の数値は、平均粒子径（ｎｍ）である。 The numerical values in Table 4 are average particle diameters (nm).
表５中の数値は、平均粒子径（ｎｍ）である。 The numerical values in Table 5 are average particle diameters (nm).
表６中の数値は、平均粒子径（ｎｍ）である。 The numerical values in Table 6 are average particle diameters (nm).
＜実施例１＞
製造例１より得た色材分散樹脂を用いて、上記＜水性色材分散液の組成＞の項に示す組成にて水性色材分散液を得て、上記＜水溶性インキ組成＞の項に示す組成により、実施例１の水溶性インキを得た。
ろ紙（Ｎｏ５ＣＡＤＶＡＮＴＥＣ社製）にて吸引ろ過し粗大粒子などを除いた。
動的光散乱法粒子測定装置（大塚電子製 ＦＰＡＲ−１０００）により平均粒子径を測定したところ、９１ｎｍとなった。
実施例１に係る水溶性インキは、６０℃７日間静置による保存安定性試験において、粒子径９５ｎｍとなり、保存安定性良好となった。
<Example 1>
Using the color material-dispersed resin obtained from Production Example 1, an aqueous color material dispersion was obtained with the composition shown in the section <Composition of water-based color material dispersion>, and the section <Water-soluble ink composition> was used. A water-soluble ink of Example 1 was obtained with the composition shown.
Suction filtration was performed with a filter paper (manufactured by No5 CADVANTEC) to remove coarse particles and the like.
When an average particle diameter was measured by a dynamic light scattering particle measuring apparatus (FPAR-1000, manufactured by Otsuka Electronics Co., Ltd.), it was 91 nm.
The water-soluble ink according to Example 1 had a particle size of 95 nm in a storage stability test by standing at 60 ° C. for 7 days, and the storage stability was good.
＜実施例２〜９＞
以降、実施例２〜９は、実施例１と同様の手順により、製造例２〜９より得た色材分散樹脂を使用し、水性色材分散液２〜９を調製し、各水溶性インキを作製したことを意味する。
実施例２〜９に係る水溶性インキは、６０℃７日間静置による保存安定性試験において、保存安定性良好となった。
<Examples 2 to 9>
Thereafter, Examples 2 to 9 use the color material dispersed resins obtained from Production Examples 2 to 9 in the same procedure as Example 1 to prepare aqueous color material dispersions 2 to 9, and each water-soluble ink. Means that
The water-soluble ink which concerns on Examples 2-9 became favorable in storage stability in the storage stability test by leaving still at 60 degreeC for 7 days.
＜実施例１０＞
製造例１より得た色材分散樹脂を用いて、上記＜水性色材分散液の組成＞の項に示す組成にてＣ．Ｉ．ピグメントブルー１５：３をＣ．Ｉ．ディスパースブルー６０に変え、同様の手順により水性色材分散液を得て、上記＜水溶性インキ組成＞の項に示す組成により、実施例１０の水溶性インキを得た。
ろ紙（Ｎｏ５ＣＡＤＶＡＮＴＥＣ社製）にて吸引ろ過し粗大粒子などを除いた。
動的光散乱法粒子測定装置（大塚電子製 ＦＰＡＲ−１０００）により平均粒子径を測定したところ、９２ｎｍとなった。
実施例１０に係る水溶性インキは、６０℃７日間静置による保存安定性試験において、粒子径９６ｎｍとなり、保存安定性良好となった。
<Example 10>
Using the color material-dispersed resin obtained from Production Example 1, the C.I. I. Pigment Blue 15: 3 to C.I. I. Instead of Disperse Blue 60, an aqueous color material dispersion was obtained by the same procedure, and the water-soluble ink of Example 10 was obtained by the composition shown in the section <Water-soluble ink composition>.
Suction filtration was performed with a filter paper (manufactured by No5 CADVANTEC) to remove coarse particles and the like.
When an average particle diameter was measured by a dynamic light scattering particle measuring apparatus (FPAR-1000, manufactured by Otsuka Electronics Co., Ltd.), it was 92 nm.
The water-soluble ink according to Example 10 had a particle size of 96 nm in a storage stability test by standing at 60 ° C. for 7 days, and the storage stability was good.
＜実施例１１＞
実施例１１では、実施例１と同様の手順により、製造例１０より得た色材分散樹脂を使用し、水性色材分散液１１を調製し、実施例１１の水溶性インキを作製した。
動的光散乱法粒子測定装置により平均粒子径を測定したところ、９４ｎｍとなった。
表５に示すように、実施例１１の水溶性インキは、６０℃７日間静置による保存安定性試験において、粒子径が９７ｎｍであり、保存安定性良好であった。
<Example 11>
In Example 11, a water-based ink of Example 11 was prepared in the same manner as in Example 1, using the color material-dispersed resin obtained in Production Example 10 to prepare an aqueous color material dispersion 11.
When the average particle diameter was measured by a dynamic light scattering particle measuring apparatus, it was 94 nm.
As shown in Table 5, the water-soluble ink of Example 11 had a particle size of 97 nm and good storage stability in a storage stability test by standing at 60 ° C. for 7 days.
＜比較例１＞
過酸化ベンゾイル使用し製造した色材分散樹脂を使用し所定の工程を経て作製した水溶性インキは、粒子径が１６２ｎｍとなった。
また、比較例１に係る水溶性インキは、保存安定性試験において、２１３ｎｍとなり保存安定性が悪かった。
<Comparative Example 1>
A water-soluble ink produced through a predetermined process using a colorant-dispersed resin produced using benzoyl peroxide has a particle diameter of 162 nm.
Further, the water-soluble ink according to Comparative Example 1 was 213 nm in the storage stability test, and the storage stability was poor.
＜比較例２＞
過酸化ラウロイルを使用し製造した色材分散樹脂を使用し所定の工程を経て作製した水溶性インキは、粒子径が１７３ｎｍとなった。
また、比較例２に係る水溶性インキは、保存安定性試験において、２５４ｎｍとなり保存安定性が悪かった。
<Comparative example 2>
The water-soluble ink produced through a predetermined process using a colorant-dispersed resin produced using lauroyl peroxide has a particle diameter of 173 nm.
Further, the water-soluble ink according to Comparative Example 2 was 254 nm in the storage stability test, and the storage stability was poor.
＜比較例３＞
分子量が３，０００の色材分散樹脂を使用し所定の工程を経て作製した水溶性インキは、粒子径が１８７ｎｍとなった。
また、比較例３に係る水溶性インキは、保存安定性試験においては、３１２ｎｍとなり保存安定性が悪かった。
<Comparative Example 3>
The water-soluble ink produced through a predetermined process using a colorant-dispersed resin having a molecular weight of 3,000 has a particle diameter of 187 nm.
In addition, the water-soluble ink according to Comparative Example 3 was 312 nm in the storage stability test, and the storage stability was poor.
＜比較例４＞
色材分散樹脂の代わりに汎用スチレン−アクリル樹脂（Ｄ−ＢＡＳＦ社製のジョンクリル６９０、重量平均分子量１６，５００）を使用し所定の工程を経て作製した水溶性インキは、粒子径が１４３ｎｍとなった。
また、比較例４に係る水溶性インキは、保存安定性試験においては、１６７ｎｍとなり保存安定性が悪かった。
<Comparative Example 4>
A water-soluble ink produced by using a general-purpose styrene-acrylic resin (Don-BASF Jonkrill 690, weight-average molecular weight 16,500) instead of the colorant-dispersing resin through a predetermined process has a particle size of 143 nm. became.
In addition, the water-soluble ink according to Comparative Example 4 was 167 nm in the storage stability test, and the storage stability was poor.
以上に、本発明の実施形態を説明したが、実施形態における各構成及びそれらの組み合わせ等は一例であり、本発明の趣旨から逸脱しない範囲内で、構成の付加、省略、置換、及びその他の変更が可能である。また、本発明は実施形態によって限定されない。 Although the embodiments of the present invention have been described above, the configurations and combinations thereof in the embodiments are examples, and the addition, omission, replacement, and other configurations of the configurations are within the scope not departing from the spirit of the present invention. It can be changed. Further, the present invention is not limited by the embodiment.
本発明の分子鎖両端に油溶性染料あるいは親油性顔料微粒子に対する親和性構造を持った構造を有する共重合体を有する色材分散剤は、水溶性インキ用の分散剤として有用である。 The colorant dispersant having a copolymer having a structure having an affinity structure for oil-soluble dyes or lipophilic pigment fine particles at both ends of the molecular chain of the present invention is useful as a dispersant for water-soluble ink.
Claims (7)
アゾ系開始剤で重合された芳香族ビニル単量体単位と不飽和カルボン酸単量体単位とを有する共重合体のアルカリ塩を備える、
色材分散剤。 A colorant dispersant,
An alkali salt of a copolymer having an aromatic vinyl monomer unit polymerized with an azo-based initiator and an unsaturated carboxylic acid monomer unit;
Colorant dispersant.
油溶性染料および親油性顔料微粒子のうち少なくとも一つと、を含む
水溶性インキ。 The colorant dispersant according to any one of claims 1 to 6,
A water-soluble ink comprising at least one of an oil-soluble dye and lipophilic pigment fine particles.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662312520P | 2016-03-24 | 2016-03-24 | |
| US62/312,520 | 2016-03-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2017171909A true JP2017171909A (en) | 2017-09-28 |
| JP6866711B2 JP6866711B2 (en) | 2021-04-28 |
Family
ID=59970593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017053584A Active JP6866711B2 (en) | 2016-03-24 | 2017-03-17 | Color material dispersant for dispersing oil-soluble dye or lipophilic pigment fine particles in water, and water-soluble ink |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP6866711B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019131491A1 (en) * | 2017-12-25 | 2019-07-04 | 三菱鉛筆株式会社 | Dispersion of colored resin fine particles for aqueous ink, and aqueous ink composition, for use in writing utensils, using same |
| JP2020204004A (en) * | 2019-06-19 | 2020-12-24 | 昭和電工マテリアルズ株式会社 | Polystyrene compound |
| KR102296033B1 (en) * | 2021-05-31 | 2021-09-01 | 주식회사 플린토 | The composite of eco water soluble ink chip |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0214207A (en) * | 1988-06-30 | 1990-01-18 | Kyowa Gas Chem Ind Co Ltd | Production of cast-molded product improved in releasablily |
| JPH11228891A (en) * | 1998-02-18 | 1999-08-24 | Fuji Xerox Co Ltd | Ink for ink jet recording |
| JP2000007967A (en) * | 1998-06-24 | 2000-01-11 | Seiko Epson Corp | Water-base ink composition, process for ink jet recording therewith, and recording recorded by using them |
| JP2005154549A (en) * | 2003-11-25 | 2005-06-16 | Seiko Epson Corp | Water-based ink composition and inkjet printing method using the same, and printed matter |
| JP2006169345A (en) * | 2004-12-15 | 2006-06-29 | Canon Inc | Inkjet pigment ink, ink set, image formation method and image recording apparatus |
| JP2006274141A (en) * | 2005-03-30 | 2006-10-12 | Dainippon Ink & Chem Inc | Aqueous dispersion for preparing ink-jet printing water-based ink and the resultant ink-jet printing water-based ink |
| JP2011219556A (en) * | 2010-04-06 | 2011-11-04 | Mitsubishi Chemicals Corp | Carbon black dispersion, ink composition, and inkjet recording method |
| JP2012158625A (en) * | 2011-01-28 | 2012-08-23 | Kyocera Document Solutions Inc | Ink for ink-jet recording apparatus |
| JP2012167222A (en) * | 2011-02-16 | 2012-09-06 | Ricoh Co Ltd | Pigment dispersion, inkjet ink using the pigment dispersion, ink cartridge, and image formation apparatus |
-
2017
- 2017-03-17 JP JP2017053584A patent/JP6866711B2/en active Active
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0214207A (en) * | 1988-06-30 | 1990-01-18 | Kyowa Gas Chem Ind Co Ltd | Production of cast-molded product improved in releasablily |
| JPH11228891A (en) * | 1998-02-18 | 1999-08-24 | Fuji Xerox Co Ltd | Ink for ink jet recording |
| JP2000007967A (en) * | 1998-06-24 | 2000-01-11 | Seiko Epson Corp | Water-base ink composition, process for ink jet recording therewith, and recording recorded by using them |
| JP2005154549A (en) * | 2003-11-25 | 2005-06-16 | Seiko Epson Corp | Water-based ink composition and inkjet printing method using the same, and printed matter |
| JP2006169345A (en) * | 2004-12-15 | 2006-06-29 | Canon Inc | Inkjet pigment ink, ink set, image formation method and image recording apparatus |
| JP2006274141A (en) * | 2005-03-30 | 2006-10-12 | Dainippon Ink & Chem Inc | Aqueous dispersion for preparing ink-jet printing water-based ink and the resultant ink-jet printing water-based ink |
| JP2011219556A (en) * | 2010-04-06 | 2011-11-04 | Mitsubishi Chemicals Corp | Carbon black dispersion, ink composition, and inkjet recording method |
| JP2012158625A (en) * | 2011-01-28 | 2012-08-23 | Kyocera Document Solutions Inc | Ink for ink-jet recording apparatus |
| JP2012167222A (en) * | 2011-02-16 | 2012-09-06 | Ricoh Co Ltd | Pigment dispersion, inkjet ink using the pigment dispersion, ink cartridge, and image formation apparatus |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019131491A1 (en) * | 2017-12-25 | 2019-07-04 | 三菱鉛筆株式会社 | Dispersion of colored resin fine particles for aqueous ink, and aqueous ink composition, for use in writing utensils, using same |
| JP2019112561A (en) * | 2017-12-25 | 2019-07-11 | 三菱鉛筆株式会社 | Dispersion liquid of coloring resin fine particles for aqueous ink, and aqueous ink composition for writing instrument using the same |
| JP7042610B2 (en) | 2017-12-25 | 2022-03-28 | 三菱鉛筆株式会社 | Water-based ink composition for stationery |
| US11560489B2 (en) | 2017-12-25 | 2023-01-24 | Mitsubishi Pencil Company, Limited | Dispersion liquid of colored resin fine particles for aqueous ink, and aqueous ink composition for writing instruments using same |
| JP2020204004A (en) * | 2019-06-19 | 2020-12-24 | 昭和電工マテリアルズ株式会社 | Polystyrene compound |
| JP7343143B2 (en) | 2019-06-19 | 2023-09-12 | 学校法人神奈川大学 | polystyrene compound |
| KR102296033B1 (en) * | 2021-05-31 | 2021-09-01 | 주식회사 플린토 | The composite of eco water soluble ink chip |
Also Published As
| Publication number | Publication date |
|---|---|
| JP6866711B2 (en) | 2021-04-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4642892B2 (en) | Pigment composition, aqueous pigment dispersion, method for producing aqueous pigment dispersion, water-based ink for inkjet recording | |
| CA2863374C (en) | Aqueous coloring agent dispersion for inkjet, ink composition, inkjet recording method, and colored body | |
| JP6609242B2 (en) | Ink composition and printing method | |
| JP2009084494A (en) | Aqueous colorant dispersion, method of producing aqueous colorant dispersion, and aqueous ink for inkjet recording | |
| JP5867659B2 (en) | Aqueous pigment composition and pigment ink | |
| JP2017171909A (en) | Colorant dispersant for dispersing oil-soluble dye or lipophilic pigment fine particles in water, and water-soluble ink | |
| WO2015072333A1 (en) | Pigment dispersant and pigment-dispersed composition containing same | |
| WO2017135011A1 (en) | Aba block copolymer, dispersant, and pigment dispersion composition | |
| JP2014196262A (en) | Triphenylmethane compound | |
| JP5583375B2 (en) | Water-based ink composition and image forming method | |
| JP2022181175A (en) | Seeded emulsion polymerization process for latexes and aqueous inkjet ink compositions made therefrom | |
| JP2011099081A (en) | Aqueous ink composition and method for forming image | |
| JP2009292900A (en) | Aqueous ink composition, ink set and image-forming method | |
| JP4633845B2 (en) | Pigment composition, method for producing aqueous pigment dispersion, and aqueous ink for inkjet recording | |
| JP2007231180A (en) | Aqueous dispersing agent and watercolor ink | |
| JP6376711B2 (en) | How to improve friction fastness | |
| JP6166685B2 (en) | How to improve friction fastness | |
| JP5513043B2 (en) | Aqueous pigment dispersions and aqueous pigment inks for writing instruments or inkjets | |
| WO2020066468A1 (en) | Pigment dispersion, inkjet ink composition and ink set obtained using said pigment dispersion, and image formed using said inkjet ink composition, and method for forming said image | |
| JP6372923B2 (en) | Ink composition and printing method | |
| JP7166532B2 (en) | Coloring material dispersion | |
| JP6166684B2 (en) | Method for improving storage stability of ink composition | |
| JP2023035200A (en) | Isoindoline pigment-containing aqueous coloring composition and colored matter | |
| JP2014201715A (en) | Xanthene compound | |
| JP2010174152A (en) | Method for manufacturing pigment dispersion liquid, pigment dispersion liquid, ink for ink jet recording, and image recording method |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RD03 | Notification of appointment of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7423 Effective date: 20181116 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20191212 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20200811 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20200901 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20201029 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20210309 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20210322 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 6866711 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |