JP2001172520A - Pigment dispersant, pigment composition, and pigment dispersion - Google Patents
Pigment dispersant, pigment composition, and pigment dispersionInfo
- Publication number
- JP2001172520A JP2001172520A JP36011399A JP36011399A JP2001172520A JP 2001172520 A JP2001172520 A JP 2001172520A JP 36011399 A JP36011399 A JP 36011399A JP 36011399 A JP36011399 A JP 36011399A JP 2001172520 A JP2001172520 A JP 2001172520A
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- benzimidazolone
- parts
- cooh
- pigments
- 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 161
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 27
- 239000000203 mixture Substances 0.000 title claims description 27
- 239000006185 dispersion Substances 0.000 title claims description 15
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract description 6
- 150000003839 salts Chemical group 0.000 claims abstract description 6
- 150000003863 ammonium salts Chemical class 0.000 claims description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- -1 alkali metal salt Chemical class 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- DSPHFASHOJAOKN-UHFFFAOYSA-N 1-[(7-oxobenzo[a]phenalen-2-yl)amino]anthracene-9,10-dione Chemical compound C1=CC2=CC(NC3=C4C(=O)C5=CC=CC=C5C(C4=CC=C3)=O)=CC(C=3C(=CC=CC=3)C3=O)=C2C3=C1 DSPHFASHOJAOKN-UHFFFAOYSA-N 0.000 claims 1
- 150000008641 benzimidazolones Chemical group 0.000 claims 1
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 abstract description 52
- 239000002687 nonaqueous vehicle Substances 0.000 abstract description 9
- 229910006069 SO3H Inorganic materials 0.000 abstract 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 239000003973 paint Substances 0.000 description 27
- 239000002966 varnish Substances 0.000 description 24
- 238000004519 manufacturing process Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- 239000000463 material Substances 0.000 description 9
- 229920000877 Melamine resin Polymers 0.000 description 7
- 239000004640 Melamine resin Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 239000000976 ink Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229920001225 polyester resin Polymers 0.000 description 4
- 239000004645 polyester resin Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229920000180 alkyd Polymers 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- WLCFKPHMRNPAFZ-UHFFFAOYSA-M didodecyl(dimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCC WLCFKPHMRNPAFZ-UHFFFAOYSA-M 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 1
- MDWZEQCQZJKVOS-UHFFFAOYSA-N 1-(1h-benzimidazol-2-yl)butane-1,3-dione Chemical compound C1=CC=C2NC(C(=O)CC(=O)C)=NC2=C1 MDWZEQCQZJKVOS-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- GVNHOISKXMSMPX-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]ethanol Chemical compound CCCCN(CCO)CCO GVNHOISKXMSMPX-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- IYVBNEJDHFJJEM-UHFFFAOYSA-N 22-methyltricosan-1-amine Chemical compound CC(C)CCCCCCCCCCCCCCCCCCCCCN IYVBNEJDHFJJEM-UHFFFAOYSA-N 0.000 description 1
- WGLQHUKCXBXUDV-UHFFFAOYSA-N 3-aminophthalic acid Chemical compound NC1=CC=CC(C(O)=O)=C1C(O)=O WGLQHUKCXBXUDV-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 229920003270 Cymel® Polymers 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical group CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N N-butylamine Natural products CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
- FHNINJWBTRXEBC-UHFFFAOYSA-N Sudan III Chemical compound OC1=CC=C2C=CC=CC2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 FHNINJWBTRXEBC-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 238000006149 azo coupling reaction Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000000981 basic dye Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 101150038956 cup-4 gene Proteins 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- QQJDHWMADUVRDL-UHFFFAOYSA-N didodecyl(dimethyl)azanium Chemical class CCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCC QQJDHWMADUVRDL-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- NAPSCFZYZVSQHF-UHFFFAOYSA-N dimantine Chemical compound CCCCCCCCCCCCCCCCCCN(C)C NAPSCFZYZVSQHF-UHFFFAOYSA-N 0.000 description 1
- 229950010007 dimantine Drugs 0.000 description 1
- UAKOZKUVZRMOFN-JDVCJPALSA-M dimethyl-bis[(z)-octadec-9-enyl]azanium;chloride Chemical compound [Cl-].CCCCCCCC\C=C/CCCCCCCC[N+](C)(C)CCCCCCCC\C=C/CCCCCCCC UAKOZKUVZRMOFN-JDVCJPALSA-M 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 235000019239 indanthrene blue RS Nutrition 0.000 description 1
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-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
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- UQKAOOAFEFCDGT-UHFFFAOYSA-N n,n-dimethyloctan-1-amine Chemical compound CCCCCCCCN(C)C UQKAOOAFEFCDGT-UHFFFAOYSA-N 0.000 description 1
- SFBHPFQSSDCYSL-UHFFFAOYSA-N n,n-dimethyltetradecan-1-amine Chemical compound CCCCCCCCCCCCCCN(C)C SFBHPFQSSDCYSL-UHFFFAOYSA-N 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- UWHRNIXHZAWBMF-UHFFFAOYSA-N n-dodecyl-n-methyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)CCCCCCCCCCCC UWHRNIXHZAWBMF-UHFFFAOYSA-N 0.000 description 1
- HKUFIYBZNQSHQS-UHFFFAOYSA-N n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC HKUFIYBZNQSHQS-UHFFFAOYSA-N 0.000 description 1
- OBJNZHVOCNPSCS-UHFFFAOYSA-N naphtho[2,3-f]quinazoline Chemical compound C1=NC=C2C3=CC4=CC=CC=C4C=C3C=CC2=N1 OBJNZHVOCNPSCS-UHFFFAOYSA-N 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 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
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 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 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
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 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
- 239000004576 sand Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000005028 tinplate Substances 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
Landscapes
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Abstract
Description
【0001】[0001]
【発明の属する技術分野】本発明は、使用適性、特に非
集合性、非結晶性、流動性に優れた顔料分散体を提供す
る顔料分散剤および顔料組成物に関する。[0001] The present invention relates to a pigment dispersant and a pigment composition which provide a pigment dispersion excellent in usability, especially non-aggregation, non-crystallinity and fluidity.
【0002】[0002]
【従来の技術】顔料の微細な粒子は、オフセットイン
キ、グラビアインキおよび塗料のような非水性ビヒクル
に分散する場合、安定な分散体を得ることが難しく、製
造作業上および得られる製品の価値に重要な影響を及ぼ
す種々の問題を引き起こすことが知られている。例え
ば、微細な粒子からなる顔料を含む分散体は、往々にし
て高粘度を示し製品の分散機からの取り出し、輸送が困
難となるばかりでなく、更に悪い場合は貯蔵中にゲル化
を起こし使用困難となることがある。また、異種の顔料
を混合して使用する場合、凝集による色分れや、沈殿な
どの現象により展色物において色むらや著しい着色力の
低下となって現れることがある。以上のような問題点に
対して、顔料に種々の置換基を導入した顔料分散剤が知
られているが、黄色系顔料、特にベンズイミダゾロン系
顔料に対しては有効な顔料分散剤は知られていなかっ
た。2. Description of the Related Art When fine particles of pigment are dispersed in non-aqueous vehicles such as offset inks, gravure inks, and paints, it is difficult to obtain a stable dispersion, and this is a problem in terms of manufacturing operations and the value of the resulting product. It is known to cause various problems that have significant effects. For example, a dispersion containing a pigment composed of fine particles often has a high viscosity, which not only makes it difficult to remove and transport the product from the disperser, but also worse, causes gelation during storage and causes use. It can be difficult. When different kinds of pigments are mixed and used, color unevenness or marked reduction in coloring power may be caused in a colored product due to phenomena such as color separation due to aggregation and precipitation. Pigment dispersants in which various substituents are introduced into pigments to solve the above problems are known, but effective pigment dispersants are known for yellow pigments, particularly benzimidazolone pigments. Had not been.
【0003】[0003]
【発明が解決しようとする課題】本発明は、顔料、特に
ベンズイミダゾロン系顔料の非水性ビヒクル中の分散に
対して有効な顔料分散剤を提供するものである。SUMMARY OF THE INVENTION The present invention provides a pigment dispersant effective for dispersing a pigment, particularly a benzimidazolone pigment, in a non-aqueous vehicle.
【0004】[0004]
【課題を解決するための手段】本発明は、下記一般式
(1)で示されるベンズイミダゾロン系顔料誘導体から
なる顔料分散剤に関する。 一般式(1)The present invention relates to a pigment dispersant comprising a benzimidazolone pigment derivative represented by the following general formula (1). General formula (1)
【化3】 式中、R1 は−CH(COCH3 )−またはナフチレン
基を表し、X1 〜X5 は、それぞれ独立に−SO3 Hも
しくはそのアルカリ金属塩もしくはアンモニウム塩、−
COOHもしくはそのアルカリ金属塩もしくはアンモニ
ウム塩、−H、−Cl、−Br、−F、−CF3 、−C
H3 、−NO2 、−OH、−OCH3 、−OC2 H5 、
−COOR2 、−OCNHC6H4CONH2、−CON
HC6 H5、−SO2NHR2 、一般式(2)で表される
基を表し(R2 は炭素数1〜4のアルキル基を表
す。)、一般式(2)Embedded image In the formula, R 1 represents —CH (COCH 3 ) — or a naphthylene group; X 1 to X 5 each independently represent —SO 3 H or an alkali metal salt or ammonium salt thereof;
COOH or alkali metal or ammonium salts thereof, -H, -Cl, -Br, -F , -CF 3, -C
H 3, -NO 2, -OH, -OCH 3, -OC 2 H 5,
-COOR 2, -OCNHC 6 H 4 CONH 2, -CON
HC 6 H 5 , —SO 2 NHR 2 , a group represented by the general formula (2) (R 2 represents an alkyl group having 1 to 4 carbon atoms), and a general formula (2)
【化4】 式(2)中、X6〜X9は、それぞれ独立に−SO3 Hも
しくはそのアルカリ金属塩もしくはアンモニウム塩、−
COOHもしくはそのアルカリ金属塩もしくはアンモニ
ウム塩、−H、−Cl、−Br、−F、−CF3 、−C
H3 、−NO2 、−OH、−OCH3 、−OC2 H5 、
−COOR2 、−CONHC6H4CONH 2、−CON
HC6 H5 、−SO2NHR2を表し(R2 は炭素数1〜
4のアルキル基を表す。)、X1 〜X9の少なくとも1
個は−SO3 Hもしくはそのアルカリ金属塩もしくはア
ンモニウム塩、または−COOHもしくはそのアルカリ
金属塩もしくはアンモニウム塩を表す(但し、X1が−
COOH、X2〜X5が−HかつR1が−CH(COC
H3)−である場合を除く。)。更に本発明は、顔料と
上記顔料分散剤とからなる顔料組成物に関する。更に本
発明は、上記顔料組成物とビヒクルとからなる顔料分散
体に関する。X1が−COOH、X2〜X5が水素原子、
R1が−CH(COCH3)−である化合物は、PY1
51の顔料として既に公知であり、この化合物は水およ
び溶剤への溶解性が極めて低く、顔料分散剤としての適
性を示さない。Embedded imageIn the formula (2), X6~ X9Are each independently -SOThree H
Or its alkali metal salt or ammonium salt,
COOH or its alkali metal salt or ammonia
Salt, -H, -Cl, -Br, -F, -CFThree , -C
HThree , -NOTwo , -OH, -OCHThree , -OCTwo HFive ,
-COORTwo , -CONHC6HFourCONH Two, -CON
HC6 HFive , -SOTwoNHRTwoRepresents (RTwo Has 1 to 1 carbon atoms
4 represents an alkyl group. ), X1 ~ X9At least one of
Is -SOThree H or its alkali metal salt or
Ammonium salt, or -COOH or its alkali
Represents a metal salt or an ammonium salt (however, X1But-
COOH, XTwo~ XFiveIs -H and R1Is -CH (COC
HThree)-Is excluded. ). Further, the present invention provides
The present invention relates to a pigment composition comprising the above pigment dispersant. More books
The invention provides a pigment dispersion comprising the pigment composition and a vehicle.
About the body. X1Is -COOH, XTwo~ XFiveIs a hydrogen atom,
R1Is -CH (COCH3)-, PY1
51, already known as pigment
Extremely low solubility in solvents and solvents, making it suitable as a pigment dispersant.
Does not show sex.
【0005】[0005]
【発明の実施の形態】ベンズイミダゾロン系顔料誘導体
の製造方法としては、アゾカップリングまたはベンズイ
ミダゾロン系顔料のスルホン化による方法があり、スル
ホン化剤として発煙硫酸、濃硫酸、クロロ硫酸などを用
いて行うのが一般的である。本発明で使用されるベンズ
イミダゾロン系顔料誘導体の代表例として下記にいくつ
か示した。DESCRIPTION OF THE PREFERRED EMBODIMENTS As a method for producing a benzimidazolone pigment derivative, there is a method by azo coupling or sulfonation of a benzimidazolone pigment. As a sulfonating agent, fuming sulfuric acid, concentrated sulfuric acid, chlorosulfuric acid or the like is used. It is common to use this. Some typical examples of the benzimidazolone pigment derivatives used in the present invention are shown below.
【0006】ベンズイミダゾロン系顔料誘導体(a)Benzimidazolone pigment derivatives (a)
【化5】 Embedded image
【0007】ベンズイミダゾロン系顔料誘導体(b)Benzimidazolone pigment derivative (b)
【化6】 Embedded image
【0008】ベンズイミダゾロン系顔料誘導体(c)Benzimidazolone pigment derivative (c)
【化7】 Embedded image
【0009】ベンズイミダゾロン系顔料誘導体(d)Benzimidazolone pigment derivative (d)
【化8】 Embedded image
【0010】ベンズイミダゾロン系顔料誘導体(e)Benzimidazolone pigment derivative (e)
【化9】 Embedded image
【0011】ベンズイミダゾロン系顔料誘導体(f)The benzimidazolone pigment derivative (f)
【化10】 Embedded image
【0012】ベンズイミダゾロン系顔料誘導体(g)Benzimidazolone pigment derivative (g)
【化11】 Embedded image
【0013】ベンズイミダゾロン系顔料誘導体(h)Benzimidazolone pigment derivative (h)
【化12】 Embedded image
【0014】ベンズイミダゾロン系顔料誘導体(i)Benzimidazolone pigment derivative (i)
【化13】 Embedded image
【0015】ベンズイミダゾロン系顔料誘導体(j)Benzimidazolone pigment derivative (j)
【化14】 Embedded image
【0016】[0016]
【0017】[0017]
【0018】ベンズイミダゾロン系顔料誘導体(k)Benzimidazolone pigment derivative (k)
【化15】 Embedded image
【0019】本発明の顔料組成物は、一般に市販されて
いるほとんどすべての顔料に効果的であるが、特に、ベ
ンズイミダゾロン系顔料の分散に効果を発揮する。本発
明に使用できる顔料としては、例えば、ベンズイミダゾ
ロン系顔料、可溶性及び不溶性アゾ顔料、縮合アゾ顔料
等のアゾ系顔料、フタロシアニン系顔料、キナクリドン
系顔料、イソインドリノン系顔料、イソインドリン系顔
料、キノフタロン系顔料、ペリレン・ペリノン系顔料、
ジオキサジン系顔料、アントラキノン系顔料、ジアンス
ラキノニル系顔料、アンスラピリミジン系顔料、アンサ
ンスロン系顔料、インダンスロン系顔料、フラバンスロ
ン系顔料、ピランスロン系顔料、ジケトピロロピロール
系顔料、建染染料系顔料、塩基性染料系顔料等の有機顔
料がある。The pigment composition of the present invention is effective for almost all commercially available pigments, but is particularly effective for dispersing benzimidazolone pigments. Examples of the pigment that can be used in the present invention include, for example, benzimidazolone pigments, azo pigments such as soluble and insoluble azo pigments, condensed azo pigments, phthalocyanine pigments, quinacridone pigments, isoindolinone pigments, and isoindoline pigments. , Quinophthalone pigments, perylene / perinone pigments,
Dioxazine pigments, Anthraquinone pigments, Dianthraquinonyl pigments, Anthrapyrimidine pigments, Ansanthrone pigments, Indanthrone pigments, Flavanthrone pigments, Pyranthrone pigments, Diketopyrrolopyrrole pigments, Vat dyes And organic pigments such as basic pigments and basic dye pigments.
【0020】ベンズイミダゾロン系顔料としては、C.
I.ピグメントイエロー120、151、154、15
6、175、180、181、194、ピグメントオレ
ンジ36、60、62、72、ピグメントレッド17
1、175、176、185、208、ピグメントバイ
オレット32、ピグメントブラウン25などがある。The benzimidazolone pigments include C.I.
I. Pigment Yellow 120, 151, 154, 15
6, 175, 180, 181, 194, Pigment Orange 36, 60, 62, 72, Pigment Red 17
1, 175, 176, 185, 208, Pigment Violet 32, Pigment Brown 25, and the like.
【0021】本発明の有機アンモニウム塩タイプの顔料
分散剤を形成するために使用されるアミン成分として
は、第1級アミン、第2級アミン、第3級アミン、第4
級アミンがある。具体的に、第1級アミンはエチルアミ
ン、プロピルアミン、イソプロピルアミン、ブチルアミ
ン、イソブチルアミン、sec−ブチルアミン、エタノ
ールアミン、イソプロパノールアミン、オクチルアミ
ン、ドデシルアミン、ラウリルアミン、ステアリルアミ
ン、オレイルアミンなど、第2級アミンはジメチルアミ
ン、ジエチルアミン、ジプロピルアミン、ジエタノール
アミン、ジステアリルアミンなど、第3級アミンはトリ
メチルアミン、トリエチルアミン、トリエタノールアミ
ン、トリイソプロパノールアミン、ジメチルエタノール
アミン、ジエチルエタノールアミン、n−ブチルジエタ
ノールアミン、N,N−ジメチル−1,3−ジアミノプ
ロパン、N,N−ジエチル−1,3−ジアミノプロパ
ン、ジメチルオクチルアミン、ジメチルデシルアミン、
ジメチルラウリルアミン、ジメチルミリスチルアミン、
ジメチルパルミチルアミン、ジメチルステアリルアミ
ン、ジメチルベヘニルアミン、ジラウリルモノメチルア
ミン、トリオクチルアミンなど、第4級アミンはジメチ
ルジドデシルアンモニウムクロライド、ジメチルジオレ
イルアンモニウムクロライド、トリメチルステアリルア
ンモニウムクロライドなどが挙げられる。The amine component used for forming the organic ammonium salt type pigment dispersant of the present invention includes a primary amine, a secondary amine, a tertiary amine and a quaternary amine.
There are secondary amines. Specifically, primary amines include secondary amines such as ethylamine, propylamine, isopropylamine, butylamine, isobutylamine, sec-butylamine, ethanolamine, isopropanolamine, octylamine, dodecylamine, laurylamine, stearylamine, and oleylamine. The amines are dimethylamine, diethylamine, dipropylamine, diethanolamine, distearylamine, etc., and the tertiary amines are trimethylamine, triethylamine, triethanolamine, triisopropanolamine, dimethylethanolamine, diethylethanolamine, n-butyldiethanolamine, N, N-dimethyl-1,3-diaminopropane, N, N-diethyl-1,3-diaminopropane, dimethyloctylamine, dimethyl Shiruamin,
Dimethyl lauryl amine, dimethyl myristyl amine,
The quaternary amines include dimethyl palmidoylamine, dimethylstearylamine, dimethylbehenylamine, dilaurylmonomethylamine, and trioctylamine. Examples of the quaternary amine include dimethyldidodecylammonium chloride, dimethyldioleylammonium chloride, and trimethylstearylammonium chloride.
【0022】本発明の顔料組成物の製造方法としては下
記の方法がある。 1.顔料と顔料分散剤を予め混合して得られる顔料組成
物を非水系ビヒクルなどに添加して分散する。 2.非水系ビヒクルなどに顔料と顔料分散剤を別々に添
加して分散する。 3.非水系ビヒクルなどに顔料と顔料分散剤を予め別々
に分散し得られた分散体を混合する。この場合、顔料分
散剤を溶媒のみで分散しても良い。 4.非水系ビヒクルなどに顔料を分散したあと、得られ
た分散体に顔料分散剤を添加する。The method for producing the pigment composition of the present invention is as follows. 1. A pigment composition obtained by previously mixing a pigment and a pigment dispersant is added to a non-aqueous vehicle or the like and dispersed. 2. A pigment and a pigment dispersant are separately added and dispersed in a non-aqueous vehicle or the like. 3. A pigment and a pigment dispersant are separately dispersed in a non-aqueous vehicle or the like, and the resulting dispersion is mixed. In this case, the pigment dispersant may be dispersed only with the solvent. 4. After dispersing the pigment in a non-aqueous vehicle or the like, a pigment dispersant is added to the resulting dispersion.
【0023】上記1で示した顔料組成物における顔料分
散剤の好ましい配合量は、顔料100重量部に対して、
0.1〜40重量部、さらに好ましくは5〜20重量部
である。顔料分散剤の配合量が上記数値より少ないと、
充分な顔料分散効果が得られず、また、上記数値より多
く配合しても用いた分の効果が得られない。The preferred compounding amount of the pigment dispersant in the pigment composition shown in the above 1 is 100 parts by weight of the pigment.
0.1 to 40 parts by weight, more preferably 5 to 20 parts by weight. If the amount of the pigment dispersant is less than the above values,
A sufficient pigment dispersing effect cannot be obtained, and the effect of the used amount cannot be obtained even if the amount is more than the above value.
【0024】顔料組成物は、顔料粉末と顔料分散剤の粉
末を単に混合して調製しても、充分目的とする効果が得
られる。しかし、ニーダー、ロール、アトライター、ス
ーパーミル等の各種粉砕機により機械的に混合するか、
顔料の水または有機溶剤によるサスペンジョン系に顔料
分散剤を含む溶液を添加し、顔料表面に顔料分散剤を吸
着させるか、硫酸等の強い溶解力を持つ溶媒に有機顔料
と顔料分散剤を共溶解して水等の貧溶媒により共沈させ
る等の緊密な混合法を行えばさらに良好な結果を得るこ
とができる。Even if the pigment composition is prepared by simply mixing the pigment powder and the pigment dispersant powder, the desired effect can be sufficiently obtained. However, mechanical mixing with various pulverizers such as kneaders, rolls, attritors, and super mills,
A solution containing a pigment dispersant is added to the suspension of the pigment in water or an organic solvent, and the pigment dispersant is adsorbed on the pigment surface, or the organic pigment and the pigment dispersant are co-dissolved in a solvent having strong dissolving power such as sulfuric acid. If a close mixing method such as coprecipitation with a poor solvent such as water is used, better results can be obtained.
【0025】また、上記2〜4で示した本発明の顔料分
散剤の使用においては、水系ビヒクルまたは水、非水系
ビヒクルまたは溶剤中への顔料あるいは顔料分散剤の分
散、これらの混合等に分散機械としてディゾルバー、ハ
イスピードミキサー、ホモミキサー、ニーダー、ロール
ミル、サンドミル、アトライター等を使用することによ
り顔料の良好な分散ができる。In the use of the pigment dispersant of the present invention as described in the above items 2 to 4, dispersion of the pigment or the pigment dispersant in an aqueous vehicle or water, a non-aqueous vehicle or a solvent, or a mixture thereof, etc. By using a dissolver, a high-speed mixer, a homomixer, a kneader, a roll mill, a sand mill, an attritor, or the like as a machine, good dispersion of the pigment can be achieved.
【0026】本発明の顔料組成物が好適に用いられるビ
ヒクルとしては、ライムロジンワニス、ポリアミド樹脂
ワニスまたは塩化ビニル樹脂ワニス等のグラビアイン
キ、ニトロセルロースラッカー、アミノアルキッド樹脂
の常乾もしくは焼き付け塗料、ウレタン系樹脂塗料、ア
クリル樹脂塗料等が挙げられる。なお、本発明の顔料組
成物の使用は非水系ビヒクルだけに限定されず、その他
の印刷インキや塗料、プラスチックの着色、さらには水
性インキ、水性塗料、エマルション型インキ、エマルシ
ョン型塗料においても、分散効果に優れ、着色力のある
着色物が得られる。The vehicle in which the pigment composition of the present invention is preferably used is a gravure ink such as lime rosin varnish, polyamide resin varnish or vinyl chloride resin varnish, nitrocellulose lacquer, amino-alkyd resin dry or baked paint, urethane Base resin paint, acrylic resin paint and the like. Note that the use of the pigment composition of the present invention is not limited to non-aqueous vehicles, and other printing inks and paints, coloring of plastics, and also aqueous inks, aqueous paints, emulsion-type inks, and emulsion-type paints can be dispersed. An excellent effect and a colored product having coloring power can be obtained.
【0027】[0027]
【実施例】以下に、実施例により本発明をさらに詳細に
説明する。例中、「部」とは「重量部」を表す。 製造例1(カップリング反応によるベンズイミダゾロン
系顔料誘導体の製造) 水200部に水酸化ナトリウム8.0部を溶解させ、3
−アミノフタル酸18.1部を加えた。これに濃塩酸5
0部を添加し、0℃以下に冷却した。次に、亜硝酸ナト
リウム7.2部を水20部に溶解させて反応系に滴下
し、5℃以下で1時間撹拌した。次に、水1000部に
水酸化ナトリウム10.4部を溶解させ、アセトアセチ
ルベンズイミダゾール23.3部を添加した。これに8
5%酢酸25.5部を添加し、上記で調整したジアゾニ
ウム塩溶液を滴下し室温で1時間撹拌した。沈殿物をろ
過、水洗、乾燥し、ベンズイミダゾロン系顔料誘導体
(a)43部を製造した。 製造例2(製造例1のドデシルアンモニウム塩の製造) 水200部に水酸化ナトリウム2.0部を溶解させ、製
造例1記載の顔料誘導体10部を添加しpH9.0にし
た。次にドデシルアミン15部を添加したあと沈殿物を
ろ過、水洗、乾燥し、ンズイミダゾロン系顔料誘導体
(b)19部を製造した。 製造例3(スルホン化反応によるベンズイミダゾロン系
顔料誘導体の製造) 顔料(PY180)50部を95重量%硫酸750部に
10℃以下で添加した。次に、昇温させ15℃で2時間
撹拌したあと、氷水に投入し析出させた。沈殿物をろ
過、食塩水で洗浄、乾燥し、ベンズイミダゾロン系顔料
誘導体(f)53部を製造した。 製造例4(製造例3のジメチルジドデシルアンモニウム
塩の製造) 水200部に水酸化ナトリウム0.5部を溶解させ、製
造例1記載の顔料誘導体5部を添加しpH9.0にし
た。次にジメチルジドデシルアンモニウムクロライド
3.5部を添加したあと沈殿物をろ過、水洗、乾燥し、
ベンズイミダゾロン系顔料誘導体(g)7.0部を製造
した。 実施例1 ベンズイミダゾロン系顔料(PY156)およびベンズ
イミダゾロン系顔料誘導体(a)を用いて下記処方によ
り塗料を作成した。塗料は、下記の配合のうち分散後添
加する混合ワニス以外の成分を容器に入れ、スチールボ
ールを加えてペイントシェイカーで分散した後、混合ワ
ニスを添加して作成した。 顔料(PY156) 9.5部 ベンズイミダゾロン系顔料誘導体(a) 0.5部 アルキド樹脂系ワニス(不揮発分60%) 26.4部 メラミン樹脂系ワニス(不揮発分50%) 13.6部 シンナー(キシレン/n−ブタノール=8/2) 20.0部 分散後添加する混合ワニス(アルキド樹脂系ワニス/メラミン樹脂系ワニス =7/3(固形分)) 48.3部 得られた塗料を下記の方法により評価したところ、良好
な流動性と途膜の光沢を示した。The present invention will be described in more detail with reference to the following examples. In the examples, “parts” means “parts by weight”. Production Example 1 (Production of benzimidazolone-based pigment derivative by coupling reaction) 8.0 parts of sodium hydroxide was dissolved in 200 parts of water, and 3
-18.1 parts of aminophthalic acid were added. Add concentrated hydrochloric acid 5
0 parts were added and cooled to below 0 ° C. Next, 7.2 parts of sodium nitrite were dissolved in 20 parts of water, added dropwise to the reaction system, and stirred at 5 ° C. or lower for 1 hour. Next, 10.4 parts of sodium hydroxide were dissolved in 1000 parts of water, and 23.3 parts of acetoacetylbenzimidazole was added. 8
25.5 parts of 5% acetic acid was added, and the diazonium salt solution prepared above was added dropwise, followed by stirring at room temperature for 1 hour. The precipitate was filtered, washed with water, and dried to produce 43 parts of a benzimidazolone pigment derivative (a). Production Example 2 (Production of Dodecyl Ammonium Salt of Production Example 1) 2.0 parts of sodium hydroxide was dissolved in 200 parts of water, and 10 parts of the pigment derivative described in Production Example 1 was added to adjust the pH to 9.0. Next, 15 parts of dodecylamine was added, and the precipitate was filtered, washed with water, and dried to produce 19 parts of a zimidazolone pigment derivative (b). Production Example 3 (Production of benzimidazolone pigment derivative by sulfonation reaction) 50 parts of pigment (PY180) was added to 750 parts of 95% by weight sulfuric acid at 10 ° C or lower. Next, the mixture was heated and stirred at 15 ° C. for 2 hours, and then poured into ice water to precipitate. The precipitate was filtered, washed with brine, and dried to produce 53 parts of a benzimidazolone pigment derivative (f). Production Example 4 (Production of dimethyldidodecylammonium salt of Production Example 3) 0.5 part of sodium hydroxide was dissolved in 200 parts of water, and 5 parts of the pigment derivative described in Production Example 1 was added to adjust the pH to 9.0. Next, 3.5 parts of dimethyldidodecylammonium chloride was added, and the precipitate was filtered, washed with water, and dried.
7.0 parts of a benzimidazolone pigment derivative (g) was produced. Example 1 A coating material was prepared using the benzimidazolone pigment (PY156) and the benzimidazolone pigment derivative (a) according to the following formulation. The paint was prepared by placing components other than the mixed varnish to be added after dispersing in the following composition into a container, adding a steel ball, dispersing with a paint shaker, and then adding the mixed varnish. Pigment (PY156) 9.5 parts Benzimidazolone pigment derivative (a) 0.5 part Alkyd resin varnish (nonvolatile content 60%) 26.4 parts Melamine resin varnish (nonvolatile content 50%) 13.6 parts Thinner (Xylene / n-butanol = 8/2) 20.0 parts Mixed varnish added after dispersion (alkyd resin varnish / melamine resin varnish = 7/3 (solid content)) 48.3 parts As a result, good fluidity and gloss of the film were shown.
【0028】塗料粘度の評価法 得られた塗料の粘度をB型粘度計にて評価した(測定温
度25℃、回転数6(r.p.m)および 60(r.p.m))。Method for Evaluating Paint Viscosity The viscosity of the obtained paint was evaluated using a B-type viscometer (measuring temperature 25 ° C., rotation speed 6 (rpm) and 60 (rpm)).
【0029】途膜光沢の評価法 得られた塗料を最終塗料粘度がフォードカップ4で23
秒になるようにシンナーで調製し、エアースプレーガン
でブリキ板に吹き付けた後焼き付け、グロスメーターで
20°グロスを測定し、塗面の鮮映性を評価した。Evaluation Method for Film Gloss The obtained paint was applied to a Ford Cup 4 having a final paint viscosity of 23.
Seconds were prepared with a thinner, sprayed on a tin plate with an air spray gun and baked, and the glossiness of the coated surface was evaluated by measuring 20 ° gloss with a gloss meter.
【0030】比較例1 実施例1においてベンズイミダゾロン系顔料誘導体
(a)を添加せず、顔料を10部とした塗料を作成し
た。得られた塗料は実施例1に比較して流動性と光沢に
劣るものであった。実施例1においてベンズイミダゾロ
ン系顔料誘導体(a)の代わりにベンズイミダゾロン系
顔料誘導体(b)、(c)(d)、(e)を用いたとこ
ろベンズイミダゾロン系顔料誘導体(i)と同等の良好
な結果が得られた。Comparative Example 1 A coating material was prepared in the same manner as in Example 1 except that the benzimidazolone-based pigment derivative (a) was not added and the pigment content was 10 parts. The obtained paint was inferior to Example 1 in fluidity and gloss. In Example 1, the benzimidazolone-based pigment derivatives (b), (c), (d), and (e) were used in place of the benzimidazolone-based pigment derivative (a). Equivalent good results were obtained.
【0031】実施例2 ベンズイミダゾロン系顔料(PR171)およびベンズ
イミダゾロン系顔料誘導体(i)を用いて下記処方によ
り塗料を作成した。塗料は、下記の配合のうち分散後添
加する混合ワニス以外の成分を容器に入れ、スチールボ
ールを加えてペイントシェイカーで分散したのち、混合
ワニスを添加して作成した。得られた塗料を実施例1と
同様にして評価したところ良好な流動性と途膜の光沢を
示した。 顔料(PR171) 9.5部 ベンズイミダゾロン系顔料誘導体(i) 0.5部 オイルフリーポリエステル樹脂系ワニス(不揮発分60%) 26.4部 メラミン樹脂系ワニス(不揮発分50%) 13.6部 スワゾール 20.0部 分散後添加する混合ワニス(オイルフリーポリエステル樹脂系ワニス/メラ ミン樹脂系ワニス=7/3(固形分)) 48.3部Example 2 A coating material was prepared using the benzimidazolone pigment (PR171) and the benzimidazolone pigment derivative (i) according to the following formulation. The paint was prepared by placing components other than the mixed varnish to be added after dispersing in the following formulation into a container, adding a steel ball, dispersing with a paint shaker, and then adding the mixed varnish. When the obtained paint was evaluated in the same manner as in Example 1, it showed good fluidity and gloss of the coating film. Pigment (PR171) 9.5 parts Benzimidazolone pigment derivative (i) 0.5 part Oil-free polyester resin varnish (nonvolatile content 60%) 26.4 parts Melamine resin varnish (nonvolatile content 50%) 13.6 Part Swazol 20.0 parts Mixed varnish added after dispersion (oil-free polyester resin varnish / melamine resin varnish = 7/3 (solid content)) 48.3 parts
【0032】比較例2 実施例2においてベンズイミダゾロン系顔料誘導体
(i)を添加せず、顔料を10部とした塗料を作成し
た。得られた塗料は実施例1に比較して流動性と光沢に
劣るものであった。実施例2においてベンズイミダゾロ
ン系顔料誘導体(i)の代わりにベンズイミダゾロン系
顔料誘導体(j)、(h)を用いたところベンズイミダ
ゾロン系顔料誘導体(i)と同等の良好な結果が得られ
た。Comparative Example 2 A coating material was prepared in the same manner as in Example 2 except that the benzimidazolone-based pigment derivative (i) was not added and the pigment content was 10 parts. The obtained paint was inferior to Example 1 in fluidity and gloss. When the benzimidazolone pigment derivative (j) and (h) were used in Example 2 in place of the benzimidazolone pigment derivative (i), good results equivalent to those of the benzimidazolone pigment derivative (i) were obtained. Was done.
【0033】実施例3 ベンズイミダゾロン系顔料(PY180)およびベンズ
イミダゾロン系顔料誘導体(f)を用いて下記処方によ
り塗料を作成した。塗料は、下記の配合のうち分散後添
加する樹脂以外の成分を容器に入れ、3mmφアルミナ
ビーズを加えてペイントコンディショナーで分散したの
ち、下記のアクリル樹脂37.5部とメチル化メラミン
樹脂(商品名サイメル303 三井サイテック製)4.
3部を添加して作成した。 顔料(PY180) 9.9部 ベンズイミダゾロン系顔料誘導体(f) 0.1部 アクリル樹脂溶液(重量平均分子量25000、酸価60、モノマー組成( 重量比)アクリル酸/ジメチルアミノエチルメタクリレート/アクリル酸エチル /メタクリル酸メチル/酢酸ビニル=7.7/15/37.3/30/10(固 形分20%)) 12.5部 イオン交換水 20.0部 得られた塗料を下記の方法により評価したところ、良好
な流動性と途膜の光沢を示した。Example 3 A coating material was prepared using the benzimidazolone pigment (PY180) and the benzimidazolone pigment derivative (f) according to the following formulation. For the paint, components other than the resin to be added after dispersion of the following formulation are put into a container, 3 mmφ alumina beads are added, and the mixture is dispersed with a paint conditioner. Then, 37.5 parts of the following acrylic resin and methylated melamine resin (trade name) 3. Cymel 303 manufactured by Mitsui Cytec)
Prepared by adding 3 parts. Pigment (PY180) 9.9 parts Benzimidazolone pigment derivative (f) 0.1 part Acrylic resin solution (weight average molecular weight 25,000, acid value 60, monomer composition (weight ratio) acrylic acid / dimethylaminoethyl methacrylate / acrylic acid Ethyl / methyl methacrylate / vinyl acetate = 7.7 / 15 / 37.3 / 30/10 (solid content 20%)) 12.5 parts Ion-exchanged water 20.0 parts As a result of the evaluation, good fluidity and gloss of the film were shown.
【0034】塗膜光沢の評価法 得られた水性塗料を4ミルのフィルムアプルケーターで
PETフィルム上に展色し、140℃で30分間焼き付
け、デジタル変角光沢計20°グロスを測定し、塗面の
鮮映性を評価した。Evaluation method of coating film gloss The obtained water-based coating material was spread on a PET film using a 4 mil film applicator, baked at 140 ° C for 30 minutes, and measured with a digital variable gloss meter at 20 ° gloss. The sharpness of the surface was evaluated.
【0035】比較例3 実施例3においてベンズイミダゾロン系顔料誘導体
(f)を添加せず、顔料を10部とした塗料を作成し
た。得られた塗料は実施例3に比較して流動性と光沢に
劣るものであった。Comparative Example 3 A coating material was prepared in the same manner as in Example 3 except that the benzimidazolone-based pigment derivative (f) was not added and the pigment content was 10 parts. The obtained paint was inferior to Example 3 in fluidity and gloss.
【0036】実施例3においてベンズイミダゾロン系顔
料誘導体(f)の代わりにベンズイミダゾロン系顔料誘
導体(a)、(b)、(c)、(d)、(e)、(g)
を用いたところベンズイミダゾロン系顔料誘導体(f)
と同等の良好な結果が得られた。In Example 3, instead of the benzimidazolone pigment derivative (f), the benzimidazolone pigment derivative (a), (b), (c), (d), (e), (g)
When a benzimidazolone pigment derivative (f) is used
As good results as were obtained.
【0037】実施例4 ベンズイミダゾロン系顔料(PY175)およびベンズ
イミダゾロン系顔料誘導体(k))を用いて下記処方に
より塗料を作成した。塗料は、下記の配合のうち分散後
添加する混合ワニス以外の成分を容器に入れ、スチール
ボールを加えてペイントシェイカーで分散したのち、混
合ワニスを添加して作成した。得られた塗料を実施例1
と同様にして評価したところ良好な流動性と途膜の光沢
を示した。 顔料(PY175) 9.5部 ベンズイミダゾロン系顔料誘導体(k) 0.5部 オイルフリーポリエステル樹脂系ワニス(不揮発分60%) 26.4部 メラミン樹脂系ワニス(不揮発分50%) 13.6部 スワゾール 20.0部 分散後添加する混合ワニス(オイルフリーポリエステル樹脂系ワニス/メラ ミン樹脂系ワニス=7/3(固形分)) 48.3部Example 4 A coating material was prepared using the benzimidazolone pigment (PY175) and the benzimidazolone pigment derivative (k) according to the following formulation. The paint was prepared by placing components other than the mixed varnish to be added after dispersing in the following formulation into a container, adding a steel ball, dispersing with a paint shaker, and then adding the mixed varnish. The obtained paint was used in Example 1
When evaluated in the same manner as above, good fluidity and gloss of the coating film were shown. Pigment (PY175) 9.5 parts Benzimidazolone pigment derivative (k) 0.5 part Oil-free polyester resin varnish (nonvolatile content 60%) 26.4 parts Melamine resin varnish (nonvolatile content 50%) 13.6 Part Swazol 20.0 parts Mixed varnish added after dispersion (oil-free polyester resin varnish / melamine resin varnish = 7/3 (solid content)) 48.3 parts
【0038】比較例4 実施例4においてベンズイミダゾロン系顔料誘導体
(k)の代わりに顔料(PY151)を添加し、顔料
(PY175)を10部とした塗料を作成した。得られ
た塗料は実施例4に比較して流動性と光沢に劣るもので
あった。 比較例5 実施例4においてベンズイミダゾロン系顔料誘導体を添
加せず、顔料(PY151)を10部とした塗料を作成
した。得られた塗料は比較例4に比較して流動性と光沢
に劣るものであった。Comparative Example 4 A pigment was prepared in the same manner as in Example 4 except that the pigment (PY151) was added instead of the benzimidazolone-based pigment derivative (k), and the pigment (PY175) was 10 parts. The obtained paint was inferior to Example 4 in fluidity and gloss. Comparative Example 5 A coating material was prepared in the same manner as in Example 4 except that the benzimidazolone-based pigment derivative was not added and the pigment (PY151) was 10 parts. The obtained paint had poor fluidity and gloss as compared with Comparative Example 4.
【0039】[0039]
【発明の効果】本発明の顔料組成物は各種ビヒクルに対
して良好な分散性を示し、分散体の粘度の低下、構造粘
性の減少等の良好な流動性を示すと同時に、色別れ、結
晶の変化等の問題がないインキや塗料が得られる。その
結果、印刷物あるいは塗膜の光沢が良く、従って美麗な
製品を得ることができる。The pigment composition of the present invention shows good dispersibility in various vehicles, shows good fluidity such as a decrease in the viscosity of the dispersion and a decrease in the structural viscosity, and at the same time, shows color separation and crystallinity. Inks and paints free from problems such as changes in color. As a result, it is possible to obtain a printed product or a coated film with good gloss and thus a beautiful product.
Claims (5)
ダゾロン系顔料誘導体からなる顔料分散剤。 一般式(1) 【化1】 式中、R1 は−CH(COCH3 )−またはナフチレン
基を表し、X1 〜X5 は、それぞれ独立に−SO3 Hも
しくはそのアルカリ金属塩もしくはアンモニウム塩、−
COOHもしくはそのアルカリ金属塩もしくはアンモニ
ウム塩、−H、−Cl、−Br、−F、−CF3 、−C
H3 、−NO2 、−OH、−OCH3 、−OC2 H5 、
−COOR2 、−CONHC6H4CONH2、−CON
HC6 H5、−SO2NHR2 、一般式(2)で表される
基を表し(R2 は炭素数1〜4のアルキル基を表
す。)、一般式(2) 【化2】 式(2)中、X6〜X9は、それぞれ独立に−SO3 Hも
しくはそのアルカリ金属塩もしくはアンモニウム塩、−
COOHもしくはそのアルカリ金属塩もしくはアンモニ
ウム塩、−H、−Cl、−Br、−F、−CF3 、−C
H3 、−NO2 、−OH、−OCH3 、−OC2 H5 、
−COOR2 、−CONHC6H4CONH 2、−CON
HC6 H5 、−SO2NHR2を表し(R2 は炭素数1〜
4のアルキル基を表す。)、X1 〜X9 の少なくとも1
個は−SO3 Hもしくはそのアルカリ金属塩もしくはア
ンモニウム塩、または−COOHもしくはそのアルカリ
金属塩もしくはアンモニウム塩を表す(但し、X1が−
COOH、X2〜X5が−HかつR1が−CH(COC
H3)−である場合を除く。)。1. A benzimid represented by the following general formula (1):
A pigment dispersant comprising a dazolone pigment derivative. General formula (1)Where R1 Is -CH (COCHThree )-Or naphthylene
X represents a group1 ~ XFive Are each independently -SOThree H
Or its alkali metal salt or ammonium salt,
COOH or its alkali metal salt or ammonia
Salt, -H, -Cl, -Br, -F, -CFThree , -C
HThree , -NOTwo , -OH, -OCHThree , -OCTwo HFive ,
-COORTwo , -CONHC6HFourCONHTwo, -CON
HC6 HFive, -SOTwoNHRTwo Represented by the general formula (2)
Represents a group (RTwo Represents an alkyl group having 1 to 4 carbon atoms.
You. ), General formula (2)In the formula (2), X6~ X9Are each independently -SOThree H
Or its alkali metal salt or ammonium salt,
COOH or its alkali metal salt or ammonia
Salt, -H, -Cl, -Br, -F, -CFThree , -C
HThree , -NOTwo , -OH, -OCHThree , -OCTwo HFive ,
-COORTwo , -CONHC6HFourCONH Two, -CON
HC6 HFive , -SOTwoNHRTwoRepresents (RTwo Has 1 to 1 carbon atoms
4 represents an alkyl group. ), X1 ~ X9 At least one of
Is -SOThree H or its alkali metal salt or
Ammonium salt, or -COOH or its alkali
Represents a metal salt or an ammonium salt (however, X1But-
COOH, XTwo~ XFiveIs -H and R1Is -CH (COC
HThree)-Is excluded. ).
の有機アンモニウム塩または−COOHの有機アンモニ
ウム塩である請求項1記載の顔料分散剤。2. At least one of X 1 to X 9 is —SO 3 H
The pigment dispersant according to claim 1, which is an organic ammonium salt of -COOH or an organic ammonium salt of -COOH.
剤とからなる顔料組成物。3. A pigment composition comprising a pigment and the pigment dispersant according to claim 1 or 2.
請求項3記載の顔料組成物。4. The pigment composition according to claim 3, wherein the pigment is a benzimidazolone pigment.
ヒクルとからなる顔料分散体。5. A pigment dispersion comprising the pigment composition according to claim 3 and a vehicle.
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005000973A1 (en) * | 2003-06-26 | 2005-01-06 | Dainippon Ink And Chemicals, Inc. | Benzimidazolone compound |
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JP2006176694A (en) * | 2004-12-24 | 2006-07-06 | Toyo Ink Mfg Co Ltd | Active energy ray curable composition |
CN1323077C (en) * | 2003-06-26 | 2007-06-27 | 大日本油墨化学工业株式会社 | Benzimidazolone compound |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS58101161A (en) * | 1981-12-14 | 1983-06-16 | Toyo Ink Mfg Co Ltd | Pigment composition |
JPS59227951A (en) * | 1983-06-10 | 1984-12-21 | Toyo Ink Mfg Co Ltd | Dispersant for pigment |
JPS6274965A (en) * | 1985-09-30 | 1987-04-06 | Konishiroku Photo Ind Co Ltd | Method of dispersing pigment |
JPH01306475A (en) * | 1988-06-03 | 1989-12-11 | Toyo Ink Mfg Co Ltd | Dispersion of pigment and pigment composition |
-
1999
- 1999-12-20 JP JP36011399A patent/JP4622016B2/en not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS58101161A (en) * | 1981-12-14 | 1983-06-16 | Toyo Ink Mfg Co Ltd | Pigment composition |
JPS59227951A (en) * | 1983-06-10 | 1984-12-21 | Toyo Ink Mfg Co Ltd | Dispersant for pigment |
JPS6274965A (en) * | 1985-09-30 | 1987-04-06 | Konishiroku Photo Ind Co Ltd | Method of dispersing pigment |
JPH01306475A (en) * | 1988-06-03 | 1989-12-11 | Toyo Ink Mfg Co Ltd | Dispersion of pigment and pigment composition |
Cited By (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005000973A1 (en) * | 2003-06-26 | 2005-01-06 | Dainippon Ink And Chemicals, Inc. | Benzimidazolone compound |
KR100704879B1 (en) * | 2003-06-26 | 2007-04-09 | 다이니혼 잉키 가가쿠 고교 가부시키가이샤 | Benzimidazolone compound |
CN1323077C (en) * | 2003-06-26 | 2007-06-27 | 大日本油墨化学工业株式会社 | Benzimidazolone compound |
US7371870B2 (en) | 2003-06-26 | 2008-05-13 | Dainippon Ink And Chemicals, Inc. | Benzimidazolone compound |
WO2006051752A1 (en) * | 2004-11-09 | 2006-05-18 | Konica Minolta Medical & Graphic, Inc. | Active energy ray-curable inkjet ink, image forming method using same, and inkjet recorder |
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