JPH02245231A - Polymer dispersant and dispersion containing the same dispersant - Google Patents
Polymer dispersant and dispersion containing the same dispersantInfo
- Publication number
- JPH02245231A JPH02245231A JP1067915A JP6791589A JPH02245231A JP H02245231 A JPH02245231 A JP H02245231A JP 1067915 A JP1067915 A JP 1067915A JP 6791589 A JP6791589 A JP 6791589A JP H02245231 A JPH02245231 A JP H02245231A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- dispersant
- hydroxyl group
- monocarboxylic acid
- dispersion
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 52
- 239000006185 dispersion Substances 0.000 title claims abstract description 48
- 229920000642 polymer Polymers 0.000 title claims abstract description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 24
- -1 glycidyl ester Chemical class 0.000 claims abstract description 21
- 229920000728 polyester Polymers 0.000 claims abstract description 10
- 239000007787 solid Substances 0.000 claims abstract description 9
- 230000002378 acidificating effect Effects 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 239000007788 liquid Substances 0.000 claims description 21
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 claims description 11
- 239000002245 particle Substances 0.000 claims description 9
- 229940114072 12-hydroxystearic acid Drugs 0.000 claims description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 5
- 239000001023 inorganic pigment Substances 0.000 claims description 5
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 5
- 239000012860 organic pigment Substances 0.000 claims description 5
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 4
- 238000007142 ring opening reaction Methods 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 claims description 2
- 229960003656 ricinoleic acid Drugs 0.000 claims description 2
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004849 alkoxymethyl group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000000049 pigment Substances 0.000 abstract description 49
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 abstract description 10
- 239000002904 solvent Substances 0.000 abstract description 9
- 230000035939 shock Effects 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 3
- 230000016615 flocculation Effects 0.000 abstract 1
- 238000005189 flocculation Methods 0.000 abstract 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 16
- 239000003973 paint Substances 0.000 description 13
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- 150000004665 fatty acids Chemical class 0.000 description 11
- 239000000976 ink Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000003981 vehicle Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 238000007639 printing Methods 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 229910001868 water Inorganic materials 0.000 description 6
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 5
- 229940072282 cardura Drugs 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 description 5
- 235000010215 titanium dioxide Nutrition 0.000 description 5
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000007667 floating Methods 0.000 description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 229920000180 alkyd Polymers 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 239000010419 fine particle Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000944 linseed oil Substances 0.000 description 3
- 235000021388 linseed oil Nutrition 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class 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 3
- 230000008569 process Effects 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- KMOUUZVZFBCRAM-UHFFFAOYSA-N 1,2,3,6-tetrahydrophthalic anhydride Chemical compound C1C=CCC2C(=O)OC(=O)C21 KMOUUZVZFBCRAM-UHFFFAOYSA-N 0.000 description 2
- FSRIVDLBMYWIAO-UHFFFAOYSA-N 1-(2-aminoethylamino)butan-2-ol Chemical compound CCC(O)CNCCN FSRIVDLBMYWIAO-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
- 241001561902 Chaetodon citrinellus Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 229920002873 Polyethylenimine Polymers 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 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
- 230000015572 biosynthetic process Effects 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000002612 dispersion medium Substances 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000003784 tall oil Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- SSUJUUNLZQVZMO-UHFFFAOYSA-N 1,2,3,4,8,9,10,10a-octahydropyrimido[1,2-a]azepine Chemical compound C1CCC=CN2CCCNC21 SSUJUUNLZQVZMO-UHFFFAOYSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- JQQXAMIFWQJQEA-UHFFFAOYSA-N 1-(2-aminoethylamino)-3-phenoxypropan-2-ol Chemical compound NCCNCC(O)COC1=CC=CC=C1 JQQXAMIFWQJQEA-UHFFFAOYSA-N 0.000 description 1
- CWKVFRNCODQPDB-UHFFFAOYSA-N 1-(2-aminoethylamino)propan-2-ol Chemical compound CC(O)CNCCN CWKVFRNCODQPDB-UHFFFAOYSA-N 0.000 description 1
- UYLNEXRLQPVSOZ-UHFFFAOYSA-N 1-[3-(hydroxymethyl)-2,2,5,5-tetramethylpyrrol-1-yl]ethanone Chemical compound CC(=O)N1C(C)(C)C=C(CO)C1(C)C UYLNEXRLQPVSOZ-UHFFFAOYSA-N 0.000 description 1
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 1
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical class CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-Hydroxyoctadecanoic acid Natural products CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- 229940105325 3-dimethylaminopropylamine Drugs 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 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
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-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
- 238000002679 ablation Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000006258 conductive agent Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling 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
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- MUTGBJKUEZFXGO-UHFFFAOYSA-N hexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21 MUTGBJKUEZFXGO-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012535 impurity 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
- 239000011261 inert gas Substances 0.000 description 1
- WTFXARWRTYJXII-UHFFFAOYSA-N iron(2+);iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+2].[Fe+3].[Fe+3] WTFXARWRTYJXII-UHFFFAOYSA-N 0.000 description 1
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 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
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 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
- 230000007774 longterm Effects 0.000 description 1
- 239000000696 magnetic material Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- PTLZMJYQEBOHHM-UHFFFAOYSA-N oxiran-2-ylmethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC1CO1 PTLZMJYQEBOHHM-UHFFFAOYSA-N 0.000 description 1
- KYVUJPJYTYQNGJ-UHFFFAOYSA-N oxiran-2-ylmethyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC1CO1 KYVUJPJYTYQNGJ-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- NVKTUNLPFJHLCG-UHFFFAOYSA-N strontium chromate Chemical compound [Sr+2].[O-][Cr]([O-])(=O)=O NVKTUNLPFJHLCG-UHFFFAOYSA-N 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は有機液体、好ましくは非極性の有機液体中に無
機或は有機液体の如き微細な粉末状固体を分散させた場
合、当該分散系に対し優れた流動性と分散安定性を賦与
することの出来る分散剤、とりわけポリエステル、アル
キッド樹脂等の塗料用ビヒクルポリマーとの相溶性が良
好な分散剤、及びこの分散剤を用いて成る分散液に関す
るものであって、その適用範囲は印刷インキや塗料の如
き被覆用組成物全般に係わるものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a dispersion system in which fine powdery solids such as inorganic or organic liquids are dispersed in an organic liquid, preferably a non-polar organic liquid. Dispersants that can provide excellent fluidity and dispersion stability to paints, particularly those that have good compatibility with paint vehicle polymers such as polyester and alkyd resins, and dispersions made using these dispersants. The scope of application is related to coating compositions such as printing inks and paints in general.
換言すれば、濃厚な顔料濃度に於て優れた流動性を示し
、且つレットダウン時のソルベントショックをも防止す
る安定な被覆用の分散液を与えることの出来る分散剤、
及びこの分散剤を用いて成る分散液を提供するものであ
る。In other words, a dispersant that can provide a stable coating dispersion that exhibits excellent fluidity at a high pigment concentration and also prevents solvent shock during letdown.
and a dispersion using this dispersant.
一般に印刷インキや塗料の様な各種被覆用の色材組成物
の構成成分である有機或は無機顔料は、微細な粉末から
成っている。印刷インキや塗料に於けるが如く、ビヒク
ルポリマーを含有する非極性有機液体に顔料粒子を分散
させた場合、特に高い顔料濃度に於いては、流動性、貯
蔵安定性の優れた色材組成物を得ることが難しく、製造
工程上並びに得られた製品の品質に重大な影響を及ぼす
様々な問題を往々にして惹起する。Organic or inorganic pigments, which are constituent components of color material compositions for various coatings such as printing inks and paints, generally consist of fine powders. When pigment particles are dispersed in a non-polar organic liquid containing a vehicle polymer, such as in printing inks and paints, the colorant composition has excellent fluidity and storage stability, especially at high pigment concentrations. are difficult to obtain and often cause various problems that seriously affect the manufacturing process and the quality of the resulting products.
即ち、微細な粒子からなる顔料の高濃度分散液は概して
流動性が悪く、分散過程に於いて混合、攪拌、練肉する
場合、或は分散機からの取り出し、容器からの移し替え
等の際に、少なからず付着ロスを生ずる如き不都合を生
ずるとか、異種顔料を混合使用した場合の色分かれ、浮
き、光沢の低下、塗装方法の相違による色違い、粘度や
光沢の経時変化など様々な好ましからざる現象が起こる
ことが知られている。In other words, highly concentrated dispersions of pigments made up of fine particles generally have poor fluidity, and when mixed, stirred, or kneaded during the dispersion process, or when taken out from a dispersion machine or transferred from a container, etc. However, there are various undesirable problems such as considerable adhesion loss, color separation when different pigments are mixed, floating, reduced gloss, color differences due to different painting methods, and changes in viscosity and gloss over time. This phenomenon is known to occur.
非水系の印刷インキ或は塗料は、ビヒクルポリマー及び
他の助剤を含有する有機液体を分散媒体とする顔料分散
体であるが、この分散体の流動学的な性質の基本的な部
分は微細粒子から成る顔料の表面性質に依存している。Non-aqueous printing inks or coatings are pigment dispersions whose dispersion medium is an organic liquid containing a vehicle polymer and other auxiliaries; the rheological properties of these dispersions are essentially due to fine particles. It depends on the surface properties of the pigment particles.
即ち、分散液の流動性が不良であったり、色分かれ、浮
きなど異常分散に係わる現象のみられる系にあっては顔
料凝集の度合か大きく、この様な分散液を用いた色材は
安定な分散状態を保持する色材に比較して、展色時の色
濃度、着色力、隠ぺい力、鮮映性が劣り、粗大凝集体に
よる凹凸のため塗面が平滑性を失い、光沢も低下する傾
向があり、従って被塗装物の商品価値を損なう。In other words, in systems where the fluidity of the dispersion is poor or where phenomena related to abnormal dispersion such as color separation or floating occur, the degree of pigment aggregation may be large, and colorants using such dispersions may be unstable. Compared to colorants that maintain a dispersed state, color density, tinting power, hiding power, and sharpness during color development are inferior, and the painted surface loses smoothness and gloss due to unevenness caused by coarse aggregates. tend to damage the commercial value of the object to be coated.
また、印刷インキや塗料のような高い顔料濃度の分散液
に於て、当該分散液の濃度、流動性を改良しようとする
と塗膜光沢が失われ、光沢を改良しようとすると流動性
が損なわれるなど、各種の適性を十分に満足するような
被覆用色材の製造は容易ではなかった。非水系の印刷イ
ンキ或は塗料中に於ける顔料の凝集を防ぐ目的で、従来
様々な方法が提案されており、それらはある程度の効果
が認められている。In addition, in dispersions with high pigment concentrations such as printing inks and paints, if you try to improve the concentration or fluidity of the dispersion, the gloss of the coating will be lost, and if you try to improve the gloss, the fluidity will be impaired. It has not been easy to produce coating coloring materials that fully satisfy various suitability requirements. Various methods have been proposed in the past for the purpose of preventing aggregation of pigments in non-aqueous printing inks or paints, and these methods have been recognized to be effective to some extent.
例えば、英国特許第９４９．７３９号、米国特許第４、
３１３．７６６号、特公昭３９−２．８８４号公報、特
開昭５２−３３．９２２号公報、特開昭５７−１２．０
６７号公報等の各明細書にはフタロシアニン顔料の分散
に有効なフタロシアニン誘導体系分散助剤が、また英国
特許第１．１３９．２９４号、米国特許第３．５３２．
５２０号の各明細書等にはジスアゾ系黄色顔料の分散に
有効な分散助剤が挙げられている。しかしながら、これ
らの分散助剤はそれによって処理される顔料か同様の色
調、或は類似骨格を有する顔料に用途が限定されるとい
う欠点がある。実質的に無色の分散剤の例としては、特
開昭５５−１１２．２７３号、英国特許第１、３１３．
７４５号、米国特許第４．２９４．６２０号、***特許
筒２．０４１．０３３号の各明細書に述べられている様
な尿素誘導体、英国特許第１．４４５．１０４号、特公
昭５８−２４、４３３号、特開昭６０−１６６、３１８
号等の各明細書に記載されている ウレタン誘導体、或
は米国特許第４、３１７．６８２号明細書に述べられて
いるアミド誘導体等が知られている。For example, British Patent No. 949.739, U.S. Patent No. 4,
No. 313.766, Japanese Patent Publication No. 39-2.884, Japanese Patent Application Publication No. 33.922-1982, Japanese Patent Application Publication No. 1987-12.0
67 and other specifications describe phthalocyanine derivative dispersion aids effective for dispersing phthalocyanine pigments, as well as British Patent No. 1.139.294 and U.S. Patent No. 3.532.
The specifications of No. 520 and the like list dispersion aids that are effective in dispersing disazo yellow pigments. However, these dispersion aids have the disadvantage that their use is limited to pigments that have a similar color tone or similar skeleton to the pigments treated with them. Examples of substantially colorless dispersants include JP-A-55-112.273 and British Patent No. 1,313.
745, U.S. Patent No. 4.294.620, West German Patent No. 2.041.033, British Patent No. 1.445.104, Japanese Patent Publication No. 1983- 24, No. 433, JP-A-60-166, 318
Urethane derivatives described in US Pat. No. 4,317,682 and amide derivatives are known.
一般に、顔料分散液を製造する過程に於いては、顔料粒
子表面の濡れ、強いせん断力による磨砕、ビヒクルポリ
マーの吸着による分散安定化の三つの過程を経て分散媒
（ビヒクル）中に混合微細化分散されるが、顔料とビヒ
クルポリマーの濡れを良くし、親和性を向上させること
を目的として従来から分散剤を使用することが良く知ら
れている。In general, in the process of manufacturing pigment dispersions, fine particles are mixed into a dispersion medium (vehicle) through three processes: wetting the pigment particle surface, grinding with strong shear force, and stabilizing the dispersion by adsorbing the vehicle polymer. However, it has been well known to use a dispersant for the purpose of improving the wetting of the pigment and vehicle polymer and improving their affinity.
これらは一般に界面活性物質であって其極性基の種類に
より、陽イオン、陰イオン、非イオン性活柱側等に分類
される。顔料の製造過程に於いて、これらの物質で処理
するとか、分散液の製造過程に於いて比較的小量を系に
添加する等の方法が従来から知られており、分散エネル
ギーの節減が可能となる。These are generally surface-active substances and are classified into cations, anions, nonionic active pillars, etc., depending on the type of polar group. Methods such as treating with these substances during the pigment manufacturing process or adding relatively small amounts to the system during the dispersion manufacturing process have been known, and it is possible to save dispersion energy. becomes.
とりわけ、かなりの汎用性を有する湿潤分散剤の例とし
ては、特公昭５４−３４．００９号、英国特許第１、３
４２．７４６号、米国特許３．７７８．２８２号の各明
細書に見られる如く、１２−ヒドロキシステアリン酸の
様なヒドロキシカルボン酸を脱水して得られる末端カル
ボキシル基含有ポリエステルまたはその塩から成る分散
剤があり、また特開昭５４−３７．０８２号、特公昭６
３−３０．０５７号、英国特許出願公開第２．００１．
０８３号、米国特許第３．８８２．０８８号、同第４．
２２４．２１２号、同第４、４１５．７０５号、***特
許出願公開第２．８３０．８６０号の各明細書には、上
記末端カルボキシル基含有ポリエステルと、ポリ（低級
アルキレンイミン）とを反応させて得られるアミン塩及
び／またはアミドから成る分散剤が記載されている。ま
た英国特許第１、４７３．３８０号明細書には、１２−
ヒドロキシステアリン酸と３−ジメチルアミノプロピル
アミンの脱水で得られるアミド系分散剤が報告されてお
り、特公昭５７−２５．２５１号、英国特許第１．３７
３．６６０号の各明細書によると、末端にカルボ牛シル
基を有するポリ（１２−ヒドロキシステアリン酸）ポリ
エステルに、ジアルキルアミノアルコールやジアルキル
アミノアル牛ルアミンを反応させて得られるエステル或
はアミド誘導体の末端３級アミン基をジメチル硫酸等の
４級化剤と反応させて得られる４級アンモニウム塩型分
散剤が報告されている。In particular, examples of wetting and dispersing agents having considerable versatility include Japanese Patent Publication No. 54-34.009 and British Patent Nos. 1 and 3.
42.746 and U.S. Pat. No. 3.778.282, a dispersion consisting of a polyester containing a terminal carboxyl group or a salt thereof obtained by dehydrating a hydroxycarboxylic acid such as 12-hydroxystearic acid. There are also JP-A No. 54-37.082 and JP-A No. 6
3-30.057, British Patent Application Publication No. 2.001.
No. 083, U.S. Patent No. 3.882.088, U.S. Patent No. 4.
No. 224.212, No. 4, 415.705, and West German Patent Application No. 2.830.860 disclose that the above-mentioned terminal carboxyl group-containing polyester is reacted with poly(lower alkylene imine). Dispersants are described which consist of amine salts and/or amides obtained in the following manner. Also, in British Patent No. 1,473.380, 12-
An amide dispersant obtained by dehydrating hydroxystearic acid and 3-dimethylaminopropylamine has been reported, and is disclosed in Japanese Patent Publication No. 57-25.251 and British Patent No. 1.37.
According to the specifications of No. 3.660, an ester or amide derivative obtained by reacting a poly(12-hydroxystearic acid) polyester having a carboxyl group at the end with a dialkylamino alcohol or a dialkylaminoalkylaminoylamine. A quaternary ammonium salt type dispersant obtained by reacting a terminal tertiary amine group with a quaternizing agent such as dimethyl sulfate has been reported.
これらのうち、特に上述のポリエステルカルボン酸アミ
ン塩及び／またはアミド系分散剤は、広い範囲の顔料に
対してかなり有効な減粘、流動化剤ではあるが、当該分
散液の分散安定性に関しては十分とは言い難く、顔料／
非極性有機溶剤／分散剤から成る、いわゆるノン・レジ
ン・べ・−スと称する分散液は、貯蔵中に顔料沈降があ
るとか、溶剤或は異種ビヒクルによる希釈の際にソルベ
ントショックと称する凝集粒子の発生が認められるなど
、多くの改良を要する点かあった。Among these, the above-mentioned polyestercarboxylic acid amine salt and/or amide dispersant are quite effective thinning and fluidizing agents for a wide range of pigments, but the dispersion stability of the dispersion liquid is It is difficult to say that there is enough pigment/
So-called non-resin based dispersions consisting of non-polar organic solvents/dispersants may suffer from pigment settling during storage or agglomerated particles known as solvent shock upon dilution with solvents or foreign vehicles. There were many points that required improvement, such as the occurrence of
本発明者等は、前記従来技術の有する課題に鑑み、鋭意
研究を重ねた結果、有機液体、好ましくは非極性の有機
液体中に微細な粉末状固体、特に有機、無機の顔料を分
散させた場合、特定の変性ポリエステル型化合物を分散
剤として用いると、高い顔料濃度に於て当該分散液中の
顔料凝集を防ぎ、ソルベントショックを起こさない安定
な分散液を形成するのに有効である事を見出し、本発明
を完成するに至った。即ち本発明は一般式（１）で表さ
れるテトラキズ（２−ヒドロキシアルキル）エチレンジ
アミン
コキシメチル、フェノキシメチル、アルケノキシメチル
、アルキル置換フェノキシメチルを表す、）１モルを、
ヒドロキル基含有高級モノカルホン酸０．５〜２０モル
及びヒドロキル基不含高級モノカルボン酸０〜２モルで
エステル化して得られる生成物に、当該生成物中のヒド
ロキシル基１当量に対して高級モノカルボン酸グリシジ
ルエステル０１〜１当量を開環付加せしめ、次いで酸性
基、塩基性基またはその両者を導入して得られる変性ポ
リエステル型化合物から成ることを特徴とする高分子分
散剤、及びこの分散剤と粉末状固体と有機液体とから成
ることを特徴とする分散液を提供するものである。In view of the above-mentioned problems with the prior art, the present inventors have conducted extensive research, and as a result, have discovered a method for dispersing fine powdery solids, particularly organic and inorganic pigments, in an organic liquid, preferably a non-polar organic liquid. In some cases, the use of certain modified polyester-type compounds as dispersants has been shown to be effective in preventing pigment aggregation in the dispersion at high pigment concentrations and forming stable dispersions that do not cause solvent shock. This discovery led to the completion of the present invention. That is, in the present invention, 1 mole of tetrakid(2-hydroxyalkyl)ethylenediaminekoxymethyl, phenoxymethyl, alkenoxymethyl, alkyl-substituted phenoxymethyl represented by the general formula (1),
A product obtained by esterification with 0.5 to 20 mol of a hydroxyl group-containing higher monocarboxylic acid and 0 to 2 mol of a hydroxyl group-free higher monocarboxylic acid is added to a higher monocarboxylic acid per equivalent of hydroxyl group in the product. A polymeric dispersant characterized by comprising a modified polyester type compound obtained by ring-opening addition of 01 to 1 equivalent of acid glycidyl ester and then introducing an acidic group, a basic group, or both, and this dispersant. The present invention provides a dispersion liquid characterized by comprising a powdery solid and an organic liquid.
一般式（Ｉ）で表されるテトラキズ（２−ヒドロキシア
ルキル）エチレンジアミンとしては、例えばテトラキズ
（２−ヒドロキシエチル）エチレンジアミン、テトラキ
ズ（２−ヒドロキシフロビル）エチレンジアミン、テト
ラキズ（２−ヒドロキシブチル）エチレンジアミン、テ
トラキズ（２−ヒドロキン−３−ｎ−ブト牛ジプロピル
）エチレンジアミン、テトラキズ（２−ヒドロキシ−３
−フェノキシプロビル）エチレンジアミン等を挙げるこ
とかできる。またこの反応で使用するヒドロキシル基含
有高級モノカルボン酸（以下ヒドロキシカルボン酸と称
す）としては、なかでも１２−ヒドロキシステアリン酸
、リシノール酸等が好適である。通常工業的に入手可能
な１２−ヒドロキシステアリン酸は、水添ひまし油の加
水分解によって製造され７）（７）で不純物として小量
のステアリン酸やパルミチン酸等が含まれているが、こ
れらの存在は本発明の分散剤を製造するのに別設支障を
来すものではない。また、ヒドロキシル基不含高級モノ
カルボン酸としては、例えば炭素数８〜２２の鎖状、分
岐状、環状のモノカルボン酸等が挙げられ、それぞれ単
独或は２種以上混合して用いる。その具体例としては、
ｎ−オクチル酸、２−エチルへ牛サン酸、ラウリル酸、
ミリスチン酸、パルミチン酸、ステアリン酸、オレイン
酸、リノール酸、リルン酸、ヤシ浦脂肪酸、大豆油脂肪
酸、牛脂脂肪酸、アマニ油脂肪酸、トール油脂肪酸、脱
水ヒマシ油脂肪酸、アビエチン酸、４−ｔｅｒＬ、−ブ
チル安息香酸等を挙げる事か出来る。更に高級モノカル
ボン酸グリシジルエステルとしては、例えばステアリン
酸グリシジルエステル、パルミチン酸グリシジルエステ
ル、ラウリン酸グリ／ジルエステル、オクチル酸グリシ
ジルエステル、ネオデカン酸グリノジルエステル（商品
名：“カージュラ”Ｅ、シェル油化エポ牛シ社製；バー
サチック酸グリシジルエステル）が好ましい。テトラキ
ズ（２−ヒドロキシアルキル）エチレンジアミン（Ｉ）
のヒドロキシカルボン酸及びヒドロキシル基不含高級モ
／カルホン酸によるエステル化反応は、公知の触媒、例
えば、ｍ酸、ｐ−トルエンスルホン酸テトラ−ｎ−フ゛
チルチタネート、テトラ−１ｓｏ−プロピルチタネート
、或は、オーストラリ、ア特許第４９３，０１５号明細
書に記載されている様に、メタンスルホン酸等の存在下
に、好ましくは窒素の様な不活性ガスを通すとか水と共
沸混合物を形成する様な芳香族炭化水素、例えばトルエ
ン、キシレン等の存在下に加熱還流して生成した水を反
応系外に共沸除去するのが有利である。エステル化の反
応温度は１２０〜２００°Ｃ１好ましくは１４０〜１８
０°Ｃであって、反応の進行度合は留出した水の同と酸
価を測定する事によって判断できる。このエステル化反
応に於て使用するヒドロキシカルボン酸の量は、テトラ
キズ （２−ヒドロキンアルキル）エチレンジアミン（
Ｉ）１モル当り、通常０．５〜２０モルであり、ヒドロ
キシカルボン酸が過剰の場合には、エステル化により（
Ｉ）の側鎖に結合したヒドロキシカルボン酸のヒドロキ
シル基が更に未反応のヒドロキシカルボン酸と脱水縮合
してポリエステル連鎖を形成するが、ポリエステル連鎖
の形成が少なく、塗膜の密着性に優れる点て、なかんず
く０．８〜３５モルか好ましい。また、ヒドロキシル基
不含高級モノカルボン酸の使用■は式（■）１モル当り
、通常０〜２，０モルである。このエステル化反応を実
施するに当たっては、（Ｉ）とヒドロキシカルボン酸及
びヒドロキシル基不含高級モノカルボン酸を同時に仕込
み、混合脱水エステル化してもよいし、（Ｉ）とヒドロ
キシカルボン酸とを脱水エステル化Ｌ、然る後にヒドロ
キシル基不含高級モノカルボン酸を加え、更に脱水エス
テル化しても良い。かくして得られる中間体生成物に高
級モノカルボン酸グリシジルエステルを開環付加させる
反応は、例えば３フツ化はう素、ジブチル錫オキサイド
、テトラ −ｎ−ブチルチタネート、テトラ−１ｓｏ−
プロピルチタネート、アルミニウムイソフロポキシド、
の如キルイス酸、或はテ）・シーｎ−ブチルアンモニウ
ムブロマイドの如き４級アンモニウム塩触媒の存在下に
加熱攪拌しつつ、上記中間体生成物中のヒドロキシル基
１当ｍに対して高級モノカルホン酸グリシジルエステル
０．１〜１．０当回、好ましくは０．８〜１当皿を徐々
に添加することによって行われる。この開環付加反応の
温度条件は１６０〜１８０ ’Ｃか好ましく、反応の進
行度合は例えばゲル・パーミエ−ンヨン・クロマトグラ
フィーで判定できるが、反応時間は通常１〜４時間で十
分である。Examples of the tetra-wound (2-hydroxyalkyl)ethylenediamine represented by the general formula (I) include tetra-wound (2-hydroxyethyl)ethylenediamine, tetra-wound (2-hydroxyfurobyl)ethylenediamine, tetra-wound (2-hydroxybutyl)ethylenediamine, and tetra-wound (2-hydroxybutyl)ethylenediamine. (2-hydroquine-3-n-butoxdipropyl) ethylenediamine, tetra-scratch (2-hydroxy-3
-phenoxypropyl) ethylenediamine and the like. Moreover, as the hydroxyl group-containing higher monocarboxylic acid (hereinafter referred to as hydroxycarboxylic acid) used in this reaction, 12-hydroxystearic acid, ricinoleic acid, etc. are particularly suitable. 12-Hydroxystearic acid, which is usually commercially available, is produced by hydrolysis of hydrogenated castor oil and contains small amounts of stearic acid and palmitic acid as impurities (7). This does not cause any trouble in producing the dispersant of the present invention. Examples of the hydroxyl group-free higher monocarboxylic acids include chain, branched, and cyclic monocarboxylic acids having 8 to 22 carbon atoms, each of which is used singly or in combination of two or more. As a specific example,
n-octylic acid, 2-ethyl bovine acid, lauric acid,
Myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, lilunic acid, palm fatty acid, soybean oil fatty acid, beef tallow fatty acid, linseed oil fatty acid, tall oil fatty acid, dehydrated castor oil fatty acid, abietic acid, 4-terL, - Butylbenzoic acid can be mentioned. Further, higher monocarboxylic acid glycidyl esters include, for example, stearic acid glycidyl ester, palmitic acid glycidyl ester, lauric acid glycidyl ester, octylic acid glycidyl ester, neodecanoic acid glinodyl ester (trade name: "Cardura" E, shell oil). Versatic acid glycidyl ester (manufactured by Kaepogushi Co., Ltd.) is preferred. Tetra-wound (2-hydroxyalkyl)ethylenediamine (I)
The esterification reaction with a hydroxycarboxylic acid and a hydroxyl-free higher mono/carphonic acid can be carried out using a known catalyst, such as m-acid, p-toluenesulfonic acid tetra-n-butyl titanate, tetra-1so-propyl titanate, or , Australia, US Pat. No. 493,015, preferably by passing an inert gas such as nitrogen or forming an azeotrope with water in the presence of methanesulfonic acid or the like. It is advantageous to azeotropically remove the water produced by heating under reflux in the presence of aromatic hydrocarbons such as toluene, xylene, etc., out of the reaction system. The reaction temperature for esterification is 120-200°C, preferably 140-18°C.
0°C, and the degree of progress of the reaction can be judged by measuring the acid value of the distilled water. The amount of hydroxycarboxylic acid used in this esterification reaction is
I) It is usually 0.5 to 20 mol per 1 mol, and if the hydroxycarboxylic acid is in excess, by esterification (
The hydroxyl group of the hydroxycarboxylic acid bonded to the side chain of I) further dehydrates and condenses with unreacted hydroxycarboxylic acid to form a polyester chain, but the formation of polyester chains is small and the adhesion of the coating film is excellent. , particularly preferably 0.8 to 35 mol. Further, the amount of the hydroxyl group-free higher monocarboxylic acid used is usually 0 to 2.0 mol per 1 mol of formula (■). In carrying out this esterification reaction, (I), a hydroxycarboxylic acid, and a hydroxyl group-free higher monocarboxylic acid may be charged simultaneously to form a mixed dehydrated ester, or (I) and a hydroxycarboxylic acid may be combined into a dehydrated ester. After that, a hydroxyl group-free higher monocarboxylic acid may be added to further dehydrate and esterify. The ring-opening addition reaction of a higher monocarboxylic acid glycidyl ester to the thus obtained intermediate product can be carried out, for example, with fluorine trifluoride, dibutyltin oxide, tetra-n-butyl titanate, tetra-1so-
Propyl titanate, aluminum isofropoxide,
While heating and stirring in the presence of a quaternary ammonium salt catalyst such as a carboxylic acid, or a quaternary ammonium salt catalyst such as te)-n-butylammonium bromide, a higher monocarphonic acid is added per equivalent of hydroxyl group in the above intermediate product. This is carried out by gradually adding 0.1 to 1.0 parts, preferably 0.8 to 1 part, of the glycidyl ester. The temperature conditions for this ring-opening addition reaction are preferably from 160 to 180'C, and the degree of progress of the reaction can be determined, for example, by gel permeability chromatography, but a reaction time of from 1 to 4 hours is usually sufficient.
このようにして得られる末端ヒドロキンル基含有ポリエ
ステルは、それ自体でも顔料分散剤として使用できるが
、顔料の種類により表面特性を異にするので、本発明で
は安定な顔料分散剤を得るためには、当該分散剤に適当
な酸性基、塩基性基またはその両者を導入する。The polyester containing a terminal hydroxyl group obtained in this way can be used as a pigment dispersant by itself, but since the surface characteristics differ depending on the type of pigment, in the present invention, in order to obtain a stable pigment dispersant, A suitable acidic group, basic group, or both are introduced into the dispersant.
酸性基の導入試剤としては、２塩基酸またはその無水物
が好ましく使用されるが、その例としては無水フタル酸
、無水マレイン酸、ｃｉｓ−△４−テトラヒドロ無水フ
タル酸、ヘキサヒドロ無水フタル酸、無水ハイミック酸
、無水コハク酸、無水ゲルタール酸、ヘット酸、イソフ
タル酸、テレフタル酸、フマール酸、アジピン酸、ピメ
リン酸、スペリン酸、アゼライン酸、セパチン酸、ドデ
カン２酸、ダイマー酸等を挙げることが出来る。As the agent for introducing acidic groups, dibasic acids or their anhydrides are preferably used, examples of which include phthalic anhydride, maleic anhydride, cis-Δ4-tetrahydrophthalic anhydride, hexahydrophthalic anhydride, and anhydride. Examples include hymic acid, succinic anhydride, geltaric anhydride, het acid, isophthalic acid, terephthalic acid, fumaric acid, adipic acid, pimelic acid, superric acid, azelaic acid, sepatic acid, dodecanedioic acid, dimer acid, etc. .
また、塩航性基の導入試剤としては例えばトリレンジイ
ソシアネート、ジフェニルメタンジイソシアネート、イ
ンフォロンジイソシアネート、キシリレンジイソシアネ
ート、ナフタレンジイソシアネート、ヘキサメチレンジ
イソシアネート及びそれらのポリ縮合体の如きインシア
ネート類とか、ポリエチレンイミン、ピペラジン、Ｎ−
アルキルピペラジン、１，４−ジアザビシクロ （２，
２，２）オクタン、１．８−ジアザビシクロ （５、４
、０）ウンデセン（７）、各種アルカノールアミン、ジ
アルキルアミノプロピルアミン及びその他のアミン類を
挙げることが出来る。Examples of agents for introducing salt-navigating groups include incyanates such as tolylene diisocyanate, diphenylmethane diisocyanate, inlon diisocyanate, xylylene diisocyanate, naphthalene diisocyanate, hexamethylene diisocyanate, and polycondensates thereof, polyethyleneimine, and piperazine. , N-
Alkylpiperazine, 1,4-diazabicyclo (2,
2,2) Octane, 1,8-diazabicyclo (5,4
, 0) undecene (7), various alkanolamines, dialkylaminopropylamine and other amines.
本発明の分散剤は、構造的に高度の立体障害を有する可
溶化基の末端に酸性または塩基性の′極性基またはその
両者を有しているので、被分散粒子に対して立体的保護
効果が大きく、安定な顔料分散液を得るのに好適である
と言う特徴があり、長時間貯蔵後も顔料の沈降分離、粘
度の経時変化が殆どなく、異種顔料を混合使用した際の
色分かれ、浮き、光沢の低下などの現象も認められず、
且つ各種の溶剤やビヒクルに対する相溶性が優れている
ので、塗料やインキの多用途ミルベース製造用分散剤と
して好適である。The dispersing agent of the present invention has an acidic or basic polar group or both at the end of the solubilizing group that has a high degree of structural steric hindrance, so it has a steric protective effect on the particles to be dispersed. It has the characteristics that it is suitable for obtaining a stable pigment dispersion, and there is almost no sedimentation and separation of pigments even after long-term storage, and there is almost no change in viscosity over time, and there is no color separation when different pigments are mixed. No phenomena such as lifting or loss of gloss were observed.
In addition, it has excellent compatibility with various solvents and vehicles, so it is suitable as a dispersant for producing a versatile mill base for paints and inks.
また本発明の分散剤は、既存のポリエステルアミン塩及
び／またはアミド型分散剤、例えば特願昭６３−１９４
．３６９号、特開昭６３−１２．３３５号、特公昭６３
−３０、０５７号の各明細書、或は米国特許第４，４１
５，７０５号明細書等に記載されているような分散剤、
英国ＩＣ１社製ソルスバーズ１３，２４０ （商品名；
ポリヒドロキシステアリン酸のポリエチレンイミン塩及
びアミド）等を併用すると更に分散効果が増大し、高い
顔料濃度でも優れた流動性を示し、且つ貯蔵安定性の良
好な塗料或はインキ用の汎用性ミルベースを得ることが
出来る。Furthermore, the dispersant of the present invention can be used in conjunction with existing polyester amine salt and/or amide type dispersants, such as Japanese Patent Application No.
．． No. 369, JP-A-63-12.335, JP-A-63
-30,057, or U.S. Patent No. 4,41
Dispersants such as those described in No. 5,705, etc.
Sols Bars 13,240 manufactured by IC1 in the UK (product name;
When used in combination with polyethyleneimine salts and amides of polyhydroxystearic acid, etc., the dispersion effect is further increased, and a versatile mill base for paints or inks that exhibits excellent fluidity even at high pigment concentrations and has good storage stability. You can get it.
本発明に係る分散液に使用する有機液体としては、例え
ばトルエン、キシレン、“ツルペッツ“１００、“ツル
ペッツ”１５０（共に商品名）の如き芳香族炭化水素；
クロロホルム、パークロロエチレン、トリクロロエチレ
ン、クロロベンゼンのヨウナハロゲン化炭化水素；メチ
ルエチルケトン、メチルイソブチルケトン、シクロヘキ
サノン、イソホロンのような鎖状或は環状のケトン類；
酢酸エチル、酢酸ブチル、酢酸アミル、セロソルブアセ
テート、カルピトールアセテートの如きエステル類；イ
ソプロピルアルコール、イソブチルアルコール、ｎ−ブ
チルアルコール、エチルセロソルブ、ブチルセロソルブ
、エチルカルピトール、ブチルカルピトールの如きアル
コール類が挙げられるが、勿論これらの２種以上の混合
溶剤であって良く、また公知のアルキッド樹脂、ポリエ
ステル樹脂、エポキシ樹脂、エポキシエステル樹脂、ポ
リウレタン樹脂、アクリル樹脂、アクリルウレタン樹脂
、ビニル樹脂、フェノール樹脂、メラミン樹脂、ニトロ
セルロース樹脂等の混合系であっても差し支えない。Examples of the organic liquid used in the dispersion according to the present invention include aromatic hydrocarbons such as toluene, xylene, and "Tsurupets" 100 and "Tsurupets" 150 (both trade names);
Halogenated hydrocarbons such as chloroform, perchloroethylene, trichloroethylene, and chlorobenzene; linear or cyclic ketones such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, and isophorone;
Esters such as ethyl acetate, butyl acetate, amyl acetate, cellosolve acetate, carpitol acetate; alcohols such as isopropyl alcohol, isobutyl alcohol, n-butyl alcohol, ethyl cellosolve, butyl cellosolve, ethyl calpitol, and butyl carpitol. However, it is of course possible to use a mixed solvent of two or more of these, and also known alkyd resins, polyester resins, epoxy resins, epoxy ester resins, polyurethane resins, acrylic resins, acrylic urethane resins, vinyl resins, phenol resins, and melamine resins. , nitrocellulose resin, etc. may be used.
本発明の分散剤によって有機液体中に分散される粉末状
固体は、通常その平均粒子径が２０μｍ以下の微細な固
体であり、例えば二酸化チタン、赤色並びに黄色或は黒
色酸化鉄、硫酸バリウム、水酸化アルミニウム、炭酸カ
ルシウム、タルク、クレー、シリカ、磁性酸化鉄、クロ
ム酸鉛、クロム酸亜鉛、クロム酸ストロンチウム、カー
ボンブラック、アルミニウム、黄銅、鉄等のような着色
剤、充填剤、電導剤、磁性剤その他を包含する各種の無
機顔料、アブ顔料、レーキ、トナー フタロシアニン顔
料、イソインドリノン顔料、ベンツイミダシロン顔料、
キナクリドン顔料、インダンスレン顔料、ジオキサジン
顔料等の有機顔料が挙げられる。なかんずく、ベンガラ
／チタン白、フタロシアニンブルー／チタン白、カーボ
ンブラック／チタン白等の混合顔料系でしばしば生ずる
色分かれ（フラディング）、浮き（フローティング）を
防ぐのに有効である。The powdery solids dispersed in the organic liquid by the dispersant of the present invention are usually fine solids with an average particle size of 20 μm or less, such as titanium dioxide, red, yellow or black iron oxide, barium sulfate, water, etc. Colorants, fillers, conductive agents, magnetic materials such as aluminum oxide, calcium carbonate, talc, clay, silica, magnetic iron oxide, lead chromate, zinc chromate, strontium chromate, carbon black, aluminum, brass, iron, etc. various inorganic pigments, including pigments, ablation pigments, lakes, toners, phthalocyanine pigments, isoindolinone pigments, benzimidasilone pigments,
Examples include organic pigments such as quinacridone pigments, indanthrene pigments, and dioxazine pigments. In particular, it is effective in preventing color separation (flooding) and floating that often occur in mixed pigment systems such as red iron/titanium white, phthalocyanine blue/titanium white, and carbon black/titanium white.
顔料分散液中に於ける本発明分散剤の相対的比率は被分
散粉体１００重量部に対して０，１〜２００重量部、好
ましくは１〜５０重量部で使用するのが有利であり、分
散液中の被分散粉体含有率は５〜８０％、好ましくは１
０〜７０重量％である。The relative proportion of the dispersant of the present invention in the pigment dispersion is advantageously 0.1 to 200 parts by weight, preferably 1 to 50 parts by weight, based on 100 parts by weight of the powder to be dispersed. The content of the dispersed powder in the dispersion is 5 to 80%, preferably 1
It is 0 to 70% by weight.
顔料分散カラーペースト或はミルベースは、それを調製
するのに、例えばボールミル、サンドミル、ロールミル
、アトライターなど通常公知の分散機を使用する。Pigment-dispersed color pastes or millbases are prepared using commonly known dispersing machines such as ball mills, sand mills, roll mills, and attritors.
以下に実施例及び試験例を挙げて本発明を更に具体的に
説明するが、勿論本発明の主旨はこれらの実施例によっ
て制限されるものではない。なお例中の部及び％は重量
基準である。The present invention will be explained in more detail below with reference to Examples and Test Examples, but the gist of the present invention is of course not limited to these Examples. Note that parts and percentages in the examples are based on weight.
実施例１ 中間体＜１）
温度計、窒素導入管、コンデンサー及び攪拌機を付した
１１の４顆フラスコにＴＨＥＥＡ（Ｎ、Ｎ。Example 1 Intermediate <1) THEEA (N, N) was placed in 11 4-cone flasks equipped with a thermometer, nitrogen inlet tube, condenser and stirrer.
Ｎ ’、 Ｎ ’−テトラキズ（２−ヒドロキシエチル
）エチレンジアミン＞１１８．２ ｇ （０，５モル）
、１２−ＨＳ Ａ （１２−ヒドロキシステアリン酸）
１５０．３ ｇ （０，５モル）、脱水ヒマシ油脂肪酸
（酸価２０１．ＯｍｇＫＯＨ／ｇ）２７９．２ｇ（１，
０当皿）、溶媒としてトルエン５０ｇ及び触媒としてオ
ルトチタン酸−ｎ−ブチル０．２ｇを仕込み、ディーン
・スタークトラップをつけた後、窒素気流中で攪拌しな
がら１３２〜１７３°Ｃで５時間還流した。N', N'-tetrakiz(2-hydroxyethyl)ethylenediamine>118.2 g (0.5 mol)
, 12-HS A (12-hydroxystearic acid)
150.3 g (0.5 mol), dehydrated castor oil fatty acid (acid value 201.0 mgKOH/g) 279.2 g (1,
After adding 50 g of toluene as a solvent and 0.2 g of n-butyl orthotitanate as a catalyst, and attaching a Dean-Stark trap, the mixture was refluxed at 132 to 173 °C for 5 hours while stirring in a nitrogen stream. did.
トラップ中に留出した水のＩは２６．１ ｇであった。The I of water distilled into the trap was 26.1 g.
次いで、触媒としてアルミニウムイソプロポキサイド０
．３ｇを添加し、滴下ロートを通じて、”カージュラ“
Ｅ−１０（商品名；シェル油化エポキシ社製；ハーサテ
ィック酸グリシジルエステル）２４５ ｇ（１，０当ｍ
）を、内温を約１６０°Ｃに保ちながら約１時間３０分
にわたって滴下した。滴下終了後、更に昇温し１８０°
Ｃに３時間保った。その後、揮発分を吸引ポンプ及び真
空ポンプにより減圧濃縮後、反応生成物を冷却し７５１
．２ｇの濃褐色油状の中間体（Ｉ）を得た。このものの
不揮発分は９８％、水酸基価は７４．１ｍｇＫＯＨ／
ｇであった。Then, aluminum isopropoxide 0 was used as a catalyst.
．． Add 3g of “Cardura” through the dropping funnel.
E-10 (trade name; manufactured by Shell Yuka Epoxy Co., Ltd.; hersatic acid glycidyl ester) 245 g (1.0 equim
) was added dropwise over a period of about 1 hour and 30 minutes while maintaining the internal temperature at about 160°C. After dropping, the temperature is further increased to 180°.
It was kept at C for 3 hours. After that, the volatile components were concentrated under reduced pressure using a suction pump and a vacuum pump, and the reaction product was cooled to 751
．． 2 g of intermediate (I) as a dark brown oil was obtained. The nonvolatile content of this product is 98%, and the hydroxyl value is 74.1mgKOH/
It was g.
実施例２ 中間体（ＩＩ） 実施例１と同様の装置に、ＴＨＰＥＡ （Ｎ、Ｎ。Example 2 Intermediate (II) In the same apparatus as in Example 1, THPEA (N, N.
Ｎ ’、 Ｎ ’−テトラキズ （２−ヒドロキシプロ
ピル）エチレンジアミン１４６．２ｇ （０，５モル
）、１２−Ｈ３Ａ １５０Ｊｇ（０，５モル）、脱水
ヒマシ油脂肪酸２７９．２ｇ （１，０当！ｔ）、ト
ルエン５０ｇ及びオルトチタン酸ｎ−ブチル０．２ｇを
仕込み、１５０〜１８８°Ｃで約７時間還流した。捕捉
した水の１は合計２５．９ ｇであった。N', N'-tetra-kiz (2-hydroxypropyl)ethylenediamine 146.2g (0.5mol), 12-H3A 150Jg (0.5mol), dehydrated castor oil fatty acid 279.2g (1.0 equivalent!t) , 50 g of toluene and 0.2 g of n-butyl orthotitanate were charged, and the mixture was refluxed at 150 to 188°C for about 7 hours. The total amount of water captured was 25.9 g.
次に、実施例１と同様にアルミニウムイソプロポキサイ
ド０３ｇを加えた後、約１６０℃に保ちなから”カージ
ュラ”Ｅ−１０２４５ｇ（１，０当■）を約１時間２０
分にわたって滴下した。その後昇温し、内温を１８０°
Ｃに３時間保った。Next, after adding 03 g of aluminum isopropoxide in the same manner as in Example 1, 245 g (1.0 kg) of "Cardura" E-10 was added for about 1 hour while keeping the temperature at about 160°C.
dripped over a period of minutes. After that, increase the temperature and bring the internal temperature to 180°
It was kept at C for 3 hours.
次いで揮発分を減圧濃縮し、７９］、、５ｇの淡赤褐色
透明油状の中間体（Ｉｆ）を得た。The volatile components were then concentrated under reduced pressure to obtain 5 g of intermediate (If) as a pale reddish brown transparent oil.
このものの不揮発分は９０％、水酸基価は７１．４ｍｇ
ＫＯＨ／ｇであった。The nonvolatile content of this product is 90%, and the hydroxyl value is 71.4 mg.
KOH/g.
実施例３ 中間体（ｍ）
実施例１と同様な装置に、ＴＨＰＥＡ １４６．２ｇ（
０，５モル）、１２− ＨＳ Ａ １５０．３ ｇ
（（１，５モル）、アマニ油脂肪酸く酸価２０１．４ｍ
ｇＫＯＩＩ／ ｇ） ２７８．６ ｇ （１，０当量）
、トルエン５０ｇ及びオルトチタン酸−ｎ−ブチル０，
２ｇを仕込み、１４２〜１８８℃で約１０時間還流した
。留出した水の１は２６．３ｇであったｔアルミニウム
イソプロポキサイド０．３ｇを添加した後、内温約１６
０°Ｃに保って“カージュラ“Ｅｌｏ ２４５ｇ （
１，０当量）を約１時間２５分にわたって滴下した。昇
温して内温を約１８０°Ｃに３時間保った。Example 3 Intermediate (m) Into the same apparatus as in Example 1, 146.2 g of THPEA (
0.5 mol), 12-HS A 150.3 g
((1.5 mol), linseed oil fatty acid acid value 201.4 m
gKOII/g) 278.6 g (1.0 equivalent)
, toluene 50g and n-butyl orthotitanate 0,
2 g was charged and refluxed at 142 to 188°C for about 10 hours. The amount of distilled water was 26.3g. After adding 0.3g of aluminum isopropoxide, the internal temperature was about 16.
Keep it at 0°C and add “Cardura” Elo 245g (
1.0 equivalents) was added dropwise over about 1 hour and 25 minutes. The temperature was increased and the internal temperature was maintained at approximately 180°C for 3 hours.
減圧濃縮して揮発分を除き、７０９．８ ｇの赤褐色油
状の中間体（ＩＩＩ）が得られた。The volatile components were removed by concentration under reduced pressure to obtain 709.8 g of intermediate (III) as a reddish brown oil.
このものの不揮発分は９７％、水酸基価は７１．６ｍｇ
Ｋｏｎ／ ｇであった。The non-volatile content of this product is 97%, and the hydroxyl value is 71.6 mg.
Kon/g.
実施例４ 中間体（ＩＶ）
実施例１と同様な装置に、Ｔ ＨＰ Ｅ Ａ １４６．
２ｇ（０，５モル）、１２− ＨＳ Ａ １５０．３
ｇ （０，５モル）、 トール油脂肪酸（酸価１９４．
ＯｍｇＫＯ１ｌ／ ｇ） ２８９．２ ｇ （１，０
当量）、トルエン５０ｇ 及びオルトチタン酸−〇−フ
チル０．２ｇを仕込ろ、１４５〜１７７°Ｃで約１１時
間還流して、２６．１ ｇの留出水を得た。Example 4 Intermediate (IV) In an apparatus similar to Example 1, T HP E A 146.
2g (0.5 mol), 12-HS A 150.3
g (0.5 mol), tall oil fatty acid (acid value 194.
OmgKO1l/g) 289.2g (1,0
(equivalent), 50 g of toluene, and 0.2 g of -0-phthyl orthotitanate were charged, and the mixture was refluxed at 145 to 177°C for about 11 hours to obtain 26.1 g of distilled water.
実施例１と同様に、アルミニウムイソプロポキサイド０
．３ｇを添加し、その後内温を約１６０℃に保って°カ
ージュラ”Ｅ −１０２４５ｇ （１，０当量）を約１
時間２０分にわたって滴下した。昇温して内温を約ｉａ
ｏ℃に３時間保った。Similar to Example 1, aluminum isopropoxide 0
．． After that, while keeping the internal temperature at about 160°C, add about 1.5 g of Cardura "E-10245 g (1.0 equivalent).
It was added dropwise over a period of 20 minutes. Raise the temperature to bring the internal temperature to about ia
It was kept at 0°C for 3 hours.
減圧ｍ緬して６６０．４ ｇの赤褐色油状の中間体（■
）を得た。660.4 g of a reddish brown oily intermediate (■
) was obtained.
このものの不揮発分は９９％、水酸基価は７０．４ｍｇ
ＫＯＲ／ｇであった。The nonvolatile content of this product is 99%, and the hydroxyl value is 70.4 mg.
KOR/g.
実施例５ 中間体（Ｖ）
実施例１と同様の装置で、ＴＲＥＥＡ １１８．２ｇ（
０，５モル）１２−ＩＳＡ １５０．３ｇ（０，５モ
ル）、アマニ油脂肪酸く酸価２０１．４ｍｇＫＯＩＩ／
ｇ）２７８．４ ｇ （１，０当量）、トルエン５０
ｇ及びオルトチタン酸−〇−ブチル０．２ ｇを仕込み
、１４３〜１８６℃で約９時間還流して、２５．９ ｇ
の水をトラップ中に捕捉した。Example 5 Intermediate (V) In the same apparatus as in Example 1, 118.2 g of TREEA (
0.5 mol) 12-ISA 150.3 g (0.5 mol), linseed oil fatty acid acid value 201.4 mg KOII/
g) 278.4 g (1.0 equivalent), toluene 50
g and 0.2 g of -butyl orthotitanate, and refluxed at 143 to 186°C for about 9 hours to produce 25.9 g.
of water was captured in the trap.
先の実施例１と同じように、アルミニウムイソプロポキ
サイド０．３ｇを添加し、内温を１５５〜１６０°Ｃに
保ッテ°カージｘ ５−Ｅ １０ ２４５ｇ （１，
０当ｍ）を約１時間３０分にわたって滴下した。その後
内温を約１８０°Ｃに３時間保持した。In the same manner as in Example 1, 0.3 g of aluminum isopropoxide was added and the internal temperature was maintained at 155 to 160°C.
0 equim) was added dropwise over about 1 hour and 30 minutes. Thereafter, the internal temperature was maintained at about 180°C for 3 hours.
実施例４と同様に処理して、７３８．３ ｇの赤褐色油
状物が得られた。Working up as in Example 4, 738.3 g of a reddish-brown oil was obtained.
このものの不揮発分は９８％、水酸基価は７４．２ｍｇ
ＫＯＨ／ｇであった。The nonvolatile content of this product is 98%, and the hydroxyl value is 74.2mg.
KOH/g.
実施例６分散剤 Ａ
温度計、窒素導入管、コンデンサー及び攪拌機をセット
した１１の４頚丸底フラスコに、実施例１で得られた中
間体（１） ７５７．２ｇ （０，５モル）及びヘキ
サヒドロ無水フタル酸（ＨＨＰＡ、 商品名リカジッ
ドＨＨ新日本理化社製） ３８．５ ｇ （０，２５モ
ル；ｌ／４当量）を仕込み、１６０〜１６４°Ｃで３時
間加熱、攪拌した。濃褐色透明な油状物となる。Example 6 Dispersant A 757.2 g (0.5 mol) of the intermediate (1) obtained in Example 1 and 38.5 g (0.25 mol; l/4 equivalent) of hexahydrophthalic anhydride (HHPA, trade name: Rikazid HH, manufactured by Shinnihon Chemical Co., Ltd.) was charged, and the mixture was heated and stirred at 160 to 164°C for 3 hours. It becomes a dark brown transparent oil.
放冷後分析し、不揮発分９９％、酸価１２．２ｍｇＫＯ
１ｌ／ｇの値を得た。Analyzed after cooling, non-volatile content 99%, acid value 12.2mgKO
A value of 1 l/g was obtained.
実施例７分散剤 Ｂ
実施例６と同様な装置に、実施例２で得られた中間体（
ＩＩ ）７５８．９ ｇ ＜０．５モル）及びヘキサヒ
ドロ無水フタル酸３８．５ ｇ （０，２５モル；１７
４当量）を仕込み、１６０〜１６６℃で３時間加熱、攪
拌した。赤褐色透明な油状物となった。Example 7 Dispersant B Into the same apparatus as in Example 6, the intermediate obtained in Example 2 (
II) 758.9 g <0.5 mol) and 38.5 g hexahydrophthalic anhydride (0.25 mol; 17
4 equivalents) and heated and stirred at 160 to 166°C for 3 hours. It became a reddish-brown transparent oil.
このものの不揮発分９８％、酸価は０．６ｍｇＫＯＨ／
ｇであった。This product has a non-volatile content of 98% and an acid value of 0.6mgKOH/
It was g.
また、ガードナー法による粘度（２５℃）は Ｑ〜Ｒ２
、色数は１１−１２、ＧＰＣによる重量平均分子量は２
１０６、数平均分子量は１９９６であった。In addition, the viscosity (25℃) according to the Gardner method is Q~R2
, color number is 11-12, weight average molecular weight by GPC is 2
106, and the number average molecular weight was 1996.
実施例８分散剤 Ｃ
実施例６と同様な装置に、実施例３で得られた中間体（
ｍ ）７８３．７ ｇ （０，５モル）及びヘキサヒド
ロ無水フ９ル酸３８．５ｇ（０，２５モル； ｌ／４当
Ｉｔ）ヲ仕込み、１６０−１６５℃で３時間２０分間加
熱、攪拌し、赤褐色油状の透明な液体が得られた。Example 8 Dispersant C The intermediate obtained in Example 3 (
m ) 783.7 g (0.5 mol) and 38.5 g (0.25 mol; l/4 equivalent It) of hexahydrofuranhydride were heated at 160-165°C for 3 hours and 20 minutes, and stirred. A reddish-brown oily clear liquid was obtained.
このものの不揮発分１００％、酸価は１．２ｍｇＫＯＩ
ｌ／ ｇであった。This product has a non-volatile content of 100% and an acid value of 1.2mg KOI.
l/g.
実施例９ 分散剤 Ｄ
実施例６と同様な装置に、実施例４で得られた中間体（
ｒＶ ）７９？、 Ｏｇ （０，５モル）及びヘキサヒ
ドロ無水フタル酸３８．５ ｇ （０，２５モル； １
／４当ｍ）を仕込み、１６０〜１６４°Ｃで３時間１０
分間加熱、攪拌し、赤褐色透明な油状液体が得られた。Example 9 Dispersant D Into the same apparatus as in Example 6, the intermediate obtained in Example 4 (
rV)79? , Og (0,5 mol) and 38.5 g of hexahydrophthalic anhydride (0,25 mol; 1
/4 tm) and heated at 160 to 164°C for 3 hours 10
After heating and stirring for a minute, a reddish-brown transparent oily liquid was obtained.
このものの不揮発分９９％、酸価は１．１ｍｇＫＯＨ／
ｇであった。This product has a non-volatile content of 99% and an acid value of 1.1mgKOH/
It was g.
実施例１０分散剤 Ｅ
実施例６と同様な装置に、実施例２で得られた中間体（
ｎ ）７５８．９ ｇ （０，５モル）及びテトラヒド
ロ無水フタル酸（Ｔ ＨＰ Ａ ：商品名 リカジッド
ＴＨ新日本理化製）３８．０ ｇ （０，２５モル；ｌ
／４当量）を仕込み、１６０〜１６２℃で３時間１５分
間加熱、攪拌した。Example 10 Dispersant E Into the same apparatus as in Example 6, the intermediate obtained in Example 2 (
n) 758.9 g (0.5 mol) and tetrahydrophthalic anhydride (THPA: trade name Rikazid TH manufactured by Shin Nihon Rika) 38.0 g (0.25 mol; l
/4 equivalent) and heated and stirred at 160 to 162°C for 3 hours and 15 minutes.
赤褐色透明な油状液体が得られた。A reddish-brown transparent oily liquid was obtained.
このものの不揮発分は９７．５％、酸価は０．８ｍｇＫ
ＯＨ／ｇであった。The nonvolatile content of this product is 97.5%, and the acid value is 0.8 mgK.
It was OH/g.
実施例１１分散剤 Ｆ
実施例６と同様な装置に、実施例２て得られた中間体（
ＩＩ） ７５８．９ｇ （０，５モル）及び無水フタ
ル酸３７、０ ｇ （０，２５モル）を仕込み、１６０
〜１６５℃で３時間加熱、攪拌した。赤褐色透明な油状
液体が得られた。Example 11 Dispersant F The intermediate obtained in Example 2 (
II) 758.9 g (0.5 mol) and 37.0 g (0.25 mol) of phthalic anhydride were charged, and 160
The mixture was heated and stirred at ~165°C for 3 hours. A reddish-brown transparent oily liquid was obtained.
このものの不揮発分は９９．５％、酸価は１． Ｏｍｇ
ＫＯＨ／ｇであった。This product has a non-volatile content of 99.5% and an acid value of 1. Omg
KOH/g.
試験例１
赤色酸化鉄１４０Ｍ （バイエル社製）４５部、実施
例７の分散剤８８部、キシレン２２部及び径３ｍｍのガ
ラスピーズ１５０部を混合し、レッドデビル社製ペイン
ト・コンディショナーを使用して １時間振とう、解膠
して顔料分散液を調製した。分散液の粘度を２５°Ｃに
於てＢ型粘度計で測定したところ、次のような結果を得
た。Test Example 1 45 parts of red iron oxide 140M (made by Bayer), 88 parts of the dispersant of Example 7, 22 parts of xylene and 150 parts of glass beads with a diameter of 3 mm were mixed, and a paint conditioner made by Red Devil was used. A pigment dispersion was prepared by shaking for 1 hour and peptizing the mixture. The viscosity of the dispersion was measured at 25°C using a B-type viscometer, and the following results were obtained.
＊チキソトロピック・インデックス二６回転粘度を６０
回回転度で割った値。*Thixotropic index 26 rotational viscosity 60
The value divided by the degree of rotation.
分散剤Ｂに代えて′ベッコゾール゛Ｊ ５２４− Ｉ
Ｍ ６０（商品名；大日本インキ化学社製アルキッド樹
脂）を使用したところビーズは動かず、得られた組成物
は非流動的であった。'Beccosol' J 524-I instead of dispersant B
When M 60 (trade name; alkyd resin manufactured by Dainippon Ink Chemical Co., Ltd.) was used, the beads did not move and the resulting composition was non-fluid.
試験例２
試験例１の分散剤Ｂに代えて、同一配合量で実施例８及
び９の分散剤Ｃ及びＤを使用した場合の分散液の粘度は
次のようであった。Test Example 2 When dispersant C and D of Examples 8 and 9 were used in the same amount in place of dispersant B of Test Example 1, the viscosity of the dispersion liquid was as follows.
分散液はいずれも良好な流動性を示し、１ケ月貯蔵後も
顔料の沈降分離によるハードケーキの形成は見られなか
った。All of the dispersions exhibited good fluidity, and no hard cake formation due to pigment sedimentation was observed even after storage for one month.
試験例３
ルチル型チタン白ＪＲ−７０１（帝国化工製）４９部、
実施例９の分散剤Ｄ８部、キシレン１８部を径３ｍｍの
ガラスピーズ１５０部と共にレッドデビル社製ペイント
コンディショナーを使用して１時間振とう、解膠して顔
料分散液を調製した。分散液の粘度を２５°Ｃで測定し
たどころ次のような結果を分散剤りに代えて”ベッコゾ
ール“Ｊ −５２４−ＩＭ−６０を同一条件で使用した
ところ、ビーズは動かず、得られた組成物は非流動的で
あった。Test Example 3 49 parts of rutile type titanium white JR-701 (manufactured by Teikoku Kako),
A pigment dispersion was prepared by shaking and peptizing 8 parts of the dispersant D of Example 9 and 18 parts of xylene together with 150 parts of glass beads having a diameter of 3 mm for 1 hour using a paint conditioner manufactured by Red Devil. When the viscosity of the dispersion was measured at 25°C, the following results were obtained. When "Beccosol" J-524-IM-60 was used under the same conditions in place of the dispersant, the beads did not move. The composition was non-flowing.
本発明は以上の如きものであるから、本発明分散剤は、
印刷インキや塗料等の非極性有機液体中に、有機、無機
の種々の顔料やフィラー等の粉末状固体を高含有率で長
期間安定に分散させることが可能で、しかも得られる本
発明分散液は、非分散微粉体が高含有率であっても、従
来のこの種の物に比して著しく低粘性および高流動性で
あるという優れた特徴を有する。Since the present invention is as described above, the dispersant of the present invention includes:
The dispersion of the present invention is capable of stably dispersing powdered solids such as various organic and inorganic pigments and fillers at a high content rate over a long period of time in non-polar organic liquids such as printing inks and paints. has the excellent characteristics of significantly lower viscosity and higher fluidity than conventional products of this type, even when the content of non-dispersed fine powder is high.
又、本発明分散剤は、分子か化学構造上多様な極性基を
有し、しかも多種類の分子が混然一体となっているため
、非分散粒子である顔料等に対して広汎な適用性を有し
、しかも広範囲の有機液体との相溶性に優れている。従
って、本発明分散剤は、異種顔料を混合使用した際の色
別れ、浮き、光沢の低下などを防止し、異種溶剤や異種
ビヒクルとの混合やそれらによる希釈の際のソルベント
ショックにもとずく凝集粒子の発生を効果的に防止する
。In addition, the dispersant of the present invention has various polar groups in its molecule or chemical structure, and since many types of molecules are mixed together, it has wide applicability to non-dispersed particles such as pigments. Moreover, it has excellent compatibility with a wide range of organic liquids. Therefore, the dispersant of the present invention prevents color separation, floating, and loss of gloss when different types of pigments are mixed and used, and prevents solvent shock when mixed with different types of solvents or vehicles or diluted with them. Effectively prevents the generation of agglomerated particles.
本発明分散剤の特徴と利点を列挙すると以下の通りであ
る。The characteristics and advantages of the dispersant of the present invention are listed below.
（イ）流動性向上による分散時間、エネルギー・コスト
の節約と分散機への仕込量増加、付着ロスの減少による
生産性の向上。(b) Improved productivity by reducing dispersion time, energy and cost by improving fluidity, increasing the amount charged to the dispersing machine, and reducing adhesion loss.
（ロ）ミル・ベース数の削減による連肉回数、貯蔵スペ
ース、在庫金利の低減。(b) Reducing the number of mills and bases, reducing the number of times the meat is processed, storage space, and inventory interest.
（ハ）ミル・ベース中の顔料濃度増加による輸送コスト
の節約。(c) Savings on transportation costs due to increased pigment concentration in the mill base.
（ニ）色剤製品中における分散状態安定化にもとづく混
合顔料の異常凝集、色別れの防止と塗膜の色濃度、光沢
等の品質の向上。(d) Prevention of abnormal agglomeration and color separation of mixed pigments and improvement of quality such as color density and gloss of paint films based on stabilization of the dispersion state in colorant products.
Claims (1)
キシアルキル）エチレンジアミン ▲数式、化学式、表等があります▼（ I ） （Ｒは、Ｈ、アルキル、フェニル、アルコキシメチル、
フェノキシメチル、アルケノキシメチル、アルキル置換
フェノキシメチルを表す）１モルを、ヒドロキシル基含
有高級モノカルボン酸０．２〜２０モル及びヒドロキシ
ル基不含高級モノカルボン酸０〜２モルでエステル化し
て得られる生成物に、当該生成物中のヒドロキシル基１
当量に対して高級モノカルボン酸グリシジルエステル０
．１〜１当量開環付加せしめ、次いで酸性基、塩基性基
またはその両者を導入して得られる変性ポリエステル型
化合物から成ることを特徴とする高分子分散剤。 ２、ヒドロキシル基含有高級モノカルボン酸がリシノー
ル酸または１２−ヒドロキシステアリン酸である請求項
１記載の高分子分散剤。 ３、高級モノカルボン酸グリシジルエステルが、ネオデ
カン酸グリシジルエステルである請求項１記載の高分子
分散剤。 ４、ヒドロキシル基不含高級モノカルボン酸が炭素数８
〜２２の鎖状、分岐及び環状モノカルボン酸から選ばれ
る少なくとも１種である請求項１記載の高分子分散剤。 ５、請求項１記載の高分子分散剤、粉末状固体及び有機
液体からなることを特徴とする分散液。 ６、粉末状固体が粒径２０μｍ以下の有機または無機顔
料である請求項５記載の分散液。[Scope of Claims] 1. Tetra-wound (2-hydroxyalkyl)ethylenediamine represented by the general formula (I) ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ (I) (R is H, alkyl, phenyl, alkoxymethyl ,
(representing phenoxymethyl, alkenoxymethyl, alkyl-substituted phenoxymethyl) is esterified with 0.2 to 20 moles of a hydroxyl group-containing higher monocarboxylic acid and 0 to 2 moles of a hydroxyl group-free higher monocarboxylic acid. The hydroxyl group 1 in the product is
Higher monocarboxylic acid glycidyl ester 0 per equivalent weight
．． A polymeric dispersant characterized by comprising a modified polyester type compound obtained by ring-opening addition of 1 to 1 equivalent and then introducing an acidic group, a basic group, or both. 2. The polymeric dispersant according to claim 1, wherein the hydroxyl group-containing higher monocarboxylic acid is ricinoleic acid or 12-hydroxystearic acid. 3. The polymer dispersant according to claim 1, wherein the higher monocarboxylic acid glycidyl ester is neodecanoic acid glycidyl ester. 4. Hydroxyl group-free higher monocarboxylic acid has 8 carbon atoms
2. The polymer dispersant according to claim 1, which is at least one selected from chain, branched, and cyclic monocarboxylic acids. 5. A dispersion liquid comprising the polymer dispersant according to claim 1, a powdery solid, and an organic liquid. 6. The dispersion according to claim 5, wherein the powdery solid is an organic or inorganic pigment with a particle size of 20 μm or less.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1067915A JPH02245231A (en) | 1989-03-20 | 1989-03-20 | Polymer dispersant and dispersion containing the same dispersant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1067915A JPH02245231A (en) | 1989-03-20 | 1989-03-20 | Polymer dispersant and dispersion containing the same dispersant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02245231A true JPH02245231A (en) | 1990-10-01 |
Family
ID=13358680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1067915A Pending JPH02245231A (en) | 1989-03-20 | 1989-03-20 | Polymer dispersant and dispersion containing the same dispersant |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02245231A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002246786A (en) * | 2001-02-19 | 2002-08-30 | Dainippon Printing Co Ltd | Radio wave absorbing body |
| JP2004224839A (en) * | 2003-01-20 | 2004-08-12 | Kimoto & Co Ltd | Hard coat coating material and molding using the same |
| EP1975702A2 (en) | 2007-03-29 | 2008-10-01 | Fujifilm Corporation | Colored photocurable composition for solid state image pick-up device, color filter and method for production thereof, and solid state image pick-up device |
| JP2011184522A (en) * | 2010-03-05 | 2011-09-22 | Sumitomo Metal Mining Co Ltd | Near-infrared shielding polyester resin composition and molded article thereof, and laminate of the molded article |
| JP2011225892A (en) * | 2004-09-09 | 2011-11-10 | Kansai Paint Co Ltd | Polyester resin |
| US8551676B2 (en) | 2007-03-30 | 2013-10-08 | Fujifilm Corporation | Pigment-dispersed composition, curable composition, and color filter and production method thereof |
| US8785087B2 (en) | 2006-12-27 | 2014-07-22 | Fujifilm Corporation | Pigment-dispersed composition, curable composition, color filter and production method thereof |
| JP2014185210A (en) * | 2013-03-22 | 2014-10-02 | Fujifilm Corp | Carbon black composition and carbon black containing coating film |
-
1989
- 1989-03-20 JP JP1067915A patent/JPH02245231A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002246786A (en) * | 2001-02-19 | 2002-08-30 | Dainippon Printing Co Ltd | Radio wave absorbing body |
| JP2004224839A (en) * | 2003-01-20 | 2004-08-12 | Kimoto & Co Ltd | Hard coat coating material and molding using the same |
| JP2011225892A (en) * | 2004-09-09 | 2011-11-10 | Kansai Paint Co Ltd | Polyester resin |
| US8785087B2 (en) | 2006-12-27 | 2014-07-22 | Fujifilm Corporation | Pigment-dispersed composition, curable composition, color filter and production method thereof |
| EP1975702A2 (en) | 2007-03-29 | 2008-10-01 | Fujifilm Corporation | Colored photocurable composition for solid state image pick-up device, color filter and method for production thereof, and solid state image pick-up device |
| US8163447B2 (en) | 2007-03-29 | 2012-04-24 | Fujifilm Corporation | Colored photocurable composition for solid state image pick-up device, color filter and method for production thereof, and solid state image pick-up device |
| US8551676B2 (en) | 2007-03-30 | 2013-10-08 | Fujifilm Corporation | Pigment-dispersed composition, curable composition, and color filter and production method thereof |
| JP2011184522A (en) * | 2010-03-05 | 2011-09-22 | Sumitomo Metal Mining Co Ltd | Near-infrared shielding polyester resin composition and molded article thereof, and laminate of the molded article |
| JP2014185210A (en) * | 2013-03-22 | 2014-10-02 | Fujifilm Corp | Carbon black composition and carbon black containing coating film |
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