JPH0511150B2 - - Google Patents
Info
- Publication number
- JPH0511150B2 JPH0511150B2 JP60210293A JP21029385A JPH0511150B2 JP H0511150 B2 JPH0511150 B2 JP H0511150B2 JP 60210293 A JP60210293 A JP 60210293A JP 21029385 A JP21029385 A JP 21029385A JP H0511150 B2 JPH0511150 B2 JP H0511150B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- pigment
- dispersant
- acid
- ink
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- -1 phosphoric acid ester compound Chemical class 0.000 claims description 63
- 239000000049 pigment Substances 0.000 claims description 58
- 239000002270 dispersing agent Substances 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 239000000976 ink Substances 0.000 description 36
- 229920000728 polyester Polymers 0.000 description 31
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 28
- 239000003973 paint Substances 0.000 description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 235000019441 ethanol Nutrition 0.000 description 23
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 229920005989 resin Polymers 0.000 description 19
- 239000011347 resin Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000003921 oil Substances 0.000 description 15
- 235000019198 oils Nutrition 0.000 description 15
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 13
- 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 13
- 239000000463 material Substances 0.000 description 13
- 150000004702 methyl esters Chemical class 0.000 description 13
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000001055 blue pigment Substances 0.000 description 12
- 238000007639 printing Methods 0.000 description 12
- 238000011010 flushing procedure Methods 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000012065 filter cake Substances 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 9
- 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 8
- 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 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 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 8
- 239000002966 varnish Substances 0.000 description 8
- 239000003981 vehicle Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 229920000180 alkyd Polymers 0.000 description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 7
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 239000003086 colorant Substances 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 230000002209 hydrophobic effect Effects 0.000 description 6
- 235000013162 Cocos nucifera Nutrition 0.000 description 5
- 244000060011 Cocos nucifera Species 0.000 description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000006229 carbon black Substances 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 230000000865 phosphorylative effect Effects 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 235000015278 beef Nutrition 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000787 lecithin Substances 0.000 description 4
- 229940067606 lecithin Drugs 0.000 description 4
- 235000010445 lecithin Nutrition 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000001459 lithography Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 4
- 229910052712 strontium Inorganic materials 0.000 description 4
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 4
- 239000003760 tallow Substances 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- 239000004640 Melamine resin Substances 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 3
- 229960003656 ricinoleic acid Drugs 0.000 description 3
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-Hydroxyoctadecanoic acid Natural products CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- QLIQIXIBZLTPGQ-UHFFFAOYSA-N 4-(2-hydroxyethoxy)benzoic acid Chemical compound OCCOC1=CC=C(C(O)=O)C=C1 QLIQIXIBZLTPGQ-UHFFFAOYSA-N 0.000 description 2
- PHOJOSOUIAQEDH-UHFFFAOYSA-N 5-hydroxypentanoic acid Chemical compound OCCCCC(O)=O PHOJOSOUIAQEDH-UHFFFAOYSA-N 0.000 description 2
- KAUQJMHLAFIZDU-UHFFFAOYSA-N 6-Hydroxy-2-naphthoic acid Chemical compound C1=C(O)C=CC2=CC(C(=O)O)=CC=C21 KAUQJMHLAFIZDU-UHFFFAOYSA-N 0.000 description 2
- IWHLYPDWHHPVAA-UHFFFAOYSA-N 6-hydroxyhexanoic acid Chemical compound OCCCCCC(O)=O IWHLYPDWHHPVAA-UHFFFAOYSA-N 0.000 description 2
- 239000004923 Acrylic lacquer Substances 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- 239000007900 aqueous suspension Substances 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
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 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 2
- IRHTZOCLLONTOC-UHFFFAOYSA-N hexacosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCO IRHTZOCLLONTOC-UHFFFAOYSA-N 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 229940097275 indigo Drugs 0.000 description 2
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 150000007974 melamines Chemical class 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 229940042880 natural phospholipid Drugs 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000007645 offset printing Methods 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 235000015096 spirit Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- 235000010215 titanium dioxide Nutrition 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000001052 yellow pigment Substances 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-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
- FWLHAQYOFMQTHQ-UHFFFAOYSA-N 2-N-[8-[[8-(4-aminoanilino)-10-phenylphenazin-10-ium-2-yl]amino]-10-phenylphenazin-10-ium-2-yl]-8-N,10-diphenylphenazin-10-ium-2,8-diamine hydroxy-oxido-dioxochromium Chemical compound O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.Nc1ccc(Nc2ccc3nc4ccc(Nc5ccc6nc7ccc(Nc8ccc9nc%10ccc(Nc%11ccccc%11)cc%10[n+](-c%10ccccc%10)c9c8)cc7[n+](-c7ccccc7)c6c5)cc4[n+](-c4ccccc4)c3c2)cc1 FWLHAQYOFMQTHQ-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
- RZJWLSPNMSHOHK-UHFFFAOYSA-N 4-methyl-1-phenylpenta-1,4-dien-3-one Chemical compound CC(=C)C(=O)C=CC1=CC=CC=C1 RZJWLSPNMSHOHK-UHFFFAOYSA-N 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- ZLFVRXUOSPRRKQ-VHEBQXMUSA-N CI Pigment Red 3 Chemical compound [O-][N+](=O)C1=CC(C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 ZLFVRXUOSPRRKQ-VHEBQXMUSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
- LIPOUNRJVLNBCD-UHFFFAOYSA-N acetyl dihydrogen phosphate Chemical compound CC(=O)OP(O)(O)=O LIPOUNRJVLNBCD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229920001893 acrylonitrile styrene Polymers 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 238000004458 analytical method Methods 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
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229960001777 castor oil Drugs 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- PZTQVMXMKVTIRC-UHFFFAOYSA-L chembl2028348 Chemical compound [Ca+2].[O-]S(=O)(=O)C1=CC(C)=CC=C1N=NC1=C(O)C(C([O-])=O)=CC2=CC=CC=C12 PZTQVMXMKVTIRC-UHFFFAOYSA-L 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 238000006298 dechlorination reaction Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- FPVGTPBMTFTMRT-NSKUCRDLSA-L fast yellow Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-NSKUCRDLSA-L 0.000 description 1
- 235000019233 fast yellow AB Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- SEPFQHJECFKHGD-UHFFFAOYSA-N henicos-2-ene Chemical group CCCCCCCCCCCCCCCCCCC=CC SEPFQHJECFKHGD-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 235000014413 iron hydroxide Nutrition 0.000 description 1
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 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
- 150000002531 isophthalic acids Chemical class 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- MOUPNEIJQCETIW-UHFFFAOYSA-N lead chromate Chemical compound [Pb+2].[O-][Cr]([O-])(=O)=O MOUPNEIJQCETIW-UHFFFAOYSA-N 0.000 description 1
- 235000010187 litholrubine BK Nutrition 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-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
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-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
- 229940099800 pigment red 48 Drugs 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 239000011029 spinel Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920005792 styrene-acrylic resin Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- TYWMIZZBOVGFOV-UHFFFAOYSA-N tetracosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCO TYWMIZZBOVGFOV-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- PDSVZUAJOIQXRK-UHFFFAOYSA-N trimethyl(octadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)C PDSVZUAJOIQXRK-UHFFFAOYSA-N 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
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Landscapes
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Coloring (AREA)
- Polyesters Or Polycarbonates (AREA)
Description
（産業上の利用分野）
本発明は新規な顔料組成物に関し、更に詳しく
はポリエステル鎖を含有するリン酸エステル化合
物を分散剤或はフラツシング助剤として使用した
塗料、印刷インキ、合成樹脂等の着色剤として有
用な顔料組成物の提供を目的とする。
（従来の技術）
従来、塗料や印刷インキの製造において、顔料
を塗料ベヒクルや印刷インキワニス中に分散させ
たり、又、水性濾過ケーキから油性ベヒクルや油
性ワニス中へフラツシングしたりする際の分散剤
又はフラツシング助剤として、例えば、リン脂質
であるレシチンが使用されてきた。
（発明が解決しようとしている問題点）
しかし、レシチンは天然品のリン脂質である
為、酸化や酸敗を受け易く、変質したり腐敗した
りする虞があり、安定で優れた性質を有する分散
剤又はフラツシング助剤として利用することが出
来る化合物が必要とされていた。
本発明者らは、上記の顔料の分散剤又はフラツ
シング助剤の欠陥に鑑み、各種のベヒクルやワニ
ス類に親和性を有し、且つ顔料に対しても親和性
を有する化合物を種々研究した結果、ヒドロキシ
ル基を有するポリエステルをリン酸と反応させて
得られるリン酸エステル化合物が優れた性質及び
効果を発揮することを見出し、本発明を完成した
ものである。
（問題点を解決する為の手段）
即ち、本発明は、顔料及び分散剤を含有する顔
料組成物において、該分散剤が、下記一般式で表
されるリン酸エステル化合物又はそれらのアンモ
ニウム塩、第１級〜第３級有機アミン塩、有機第
４級アンモニウム塩又は１〜３価の金属塩である
ことを特徴とする顔料組成物である。
［但しR1は、炭素数４〜30の炭化水素基である。
R2は、R3OOC−R1［―Ｏ・OC−R1〕―o、水素原子
又は炭素数１〜30の炭化水素基である。R3は水
素原子又は炭素数１〜30の炭化水素基である。ｎ
は１以上で分子量が10000以下になる値である。］
（好ましい実施態様）
本発明を詳細に説明すると、本発明において使
用し、本発明を主として特徴づける分散剤は、特
定の上記定義のリン酸エステル化合物である。
本発明で使用するリン酸エステル化合物は、リ
ン酸化剤１モルに対し、必須成分として１モル又
は２モルのポリエステルアルコール成分を従来公
知の方法に準じて反応させることによつて得られ
る。
リン酸化剤としては従来公知のオキシ塩化リ
ン、五酸化リン、三塩化リン、無水リン酸、アセ
チルリン酸等が使用される。オキシ塩化リンが最
も好ましいリン酸化剤である。
反応条件としては、オキシ塩化リンの場合、最
初のエステル化反応が激しい為、低温で反応させ
ることが好ましく、反応を促進させる為に反応装
置を減圧にして発生する塩化水素を除去すること
も出来る。又、反応を完結させるには加熱するこ
とも好ましい。
反応終了後は、未反応の塩化物は、湯、温水、
冷水等で洗浄して加水分解する。又、ハロゲン化
リン化合物を使用する場合、塩基性触媒を使用す
ることも好ましく、例えば、トリエチルアミン等
の第三級アミン類、ピリジン、２，６−ルチジ
ン、１，８−ジアザ−ビシクロ（５，４，０）ウ
ンデセン−７等の有機塩基、アルカリ金属、アル
カリ土類金属の酸化物、水酸化物、炭酸塩、有機
酸塩等の顕在又は潜在の無機塩基を使用すること
が出来、反応後、濾過、中和、水洗等によりハロ
ゲン化物、塩、塩基その他の不純物を除くことが
好ましい。
反応させるポリエステルアルコール成分は、そ
の生成物の目的によつて種々選択して使用する。
本発明で使用するリン酸エステル化合物は、目
的化合物で合致したポリエステルアルコール成分
等をリン酸化剤に直接反応させて目的物を得る
他、予め、例えば、12−ヒドロキシステアリン酸
のメチルエステル等と反応させて、末端がメチル
エステル等のジ又はモノリン酸エステルを合成
し、次いで該メチルエステルを加水分解し、それ
と12−ヒドロキシステアリン酸のポリエステル又
は更に他のアルコール類と脱メタノール反応で縮
合させて該ポリエステルのリン酸ジ又はモノエス
テル化合物を合成する等の方法によつても得られ
る。
使用するポリエステルアルコール成分は従来公
知の水酸基を有する脂肪族、脂環族及び芳香のカ
ルボン酸又はそのポリエステルである。
使用されるポリエステルアルコール成分の分子
量は、特に規制されるものではないが、二量体〜
平均分子量約10000以下、好ましくは約500〜約
5000である。
この様なポリエステルアルコール成分として
は、例えば、下記の如きものが使用される。
(A) ヒドロキシカルボン酸の自己縮合ポリエステ
ル類、好ましくは炭素数４〜30の炭化水素鎖を
含むヒドロキシカルボン酸のポリエステル。
例えば、リシノレイン酸、リシノール酸、12
−ヒドロキシステアリン酸、ヒマシ油脂肪酸、
水添ヒマシ油脂肪酸、δ−ヒドロキシ吉草酸、
ε−ヒドロキシカプロン酸、ｐ−ヒドロキシエ
チルオキシ安息香酸、２−ヒドロキシナフタレ
ン−６−カルボン酸等のヒドロキシカルボン酸
から選ばれた一種又は二種以上の自己縮合ポリ
エステルが挙げられる。
(B) 上記(A)で述べたポリエステルアルコール成分
の他端のカルボン酸のエステル化物。
これらは炭素数１〜30の脂肪族、脂環族又は芳
香族のアルコール類とのエステルであり、例え
ば、上記のポリエステルのメチル−、エチル−、
プロピル−、ブチル−、ヘキシル−、オクチル
−、ドデシル−、ヘキサデシル−、オクタデシル
−、シクロヘキシル−、ベンジル−アルコール等
のエステルが挙げられる。
本発明で使用するリン酸エステル化合物は、上
記のポリエステルアルコール成分のリン酸ジエス
テル化合物の他、該ポリエステルアルコール成分
とリン酸化剤との反応をモノエステルに留め、他
のモノエステル分を従来公知のヒドロキシカルボ
ン酸、ヒドロキシカルボン酸のアルコールエステ
ル又はアルコールを用いてエステル化した非対称
リン酸ジエステル化合物も含まれ、従来公知の非
対称リン酸ジエステル化合物の合成方法に準じて
合成することが出来る。
これらのアルコール成分は、従来公知のものが
使用され、例えば、ヒドロキシカルボン酸及びそ
のアルコールエステルとしては、リシノール酸、
12−ヒドロキシステアリン酸、γ−ヒドロキシ酪
酸、δ−ヒドロキシ吉草酸、ε−ヒドロキシカプ
ロン酸、ｐ−ヒドロキシエチルオキシ安息香酸、
２−ヒドロキシナフタレン−６−カルボン酸等及
びそれらと炭素数１〜30のアルコールとのエステ
ルであり、アルコールとしては、炭素数１〜30の
アルコールであり、例えば、メチルアルコール、
エチルアルコール、プロピルアルコール、ブチル
アルコール、ヘキシルアルコール、オクチルアル
コール、デシルアルコール、ドデシルアルコー
ル、トリデシルアルコール、ヘキサデシルアルコ
ール、オクタデシルアルコール、テトラコシルア
ルコール、ヘキサコシルアルコール、オクタデセ
ニルアルコール、シクロヘキシルアルコール、ベ
ンジルアルコール等が挙げられる。
上記の本発明を使用するポリエステルアルコー
ルを必須成分とするアルコール成分のリン酸エス
テル化反応にあたつては、これらの原料及び生成
物に対して不活性であり、且つそれらの原料等を
溶解する有機溶媒を使用することも好ましい。
例えば、オクタン、石油エーテル、リグロイ
ン、ミネラルスピリツト、ケロシン等の脂肪族飽
和炭化水素、ベンゼン、トルエン、キシレン等の
芳香族炭化水素、トリクロルエタン、テトラクロ
ルエタン等のハロゲン化脂肪族炭化水素、ｏ−ジ
クロルベンゼン、トリクロルベンゼン等の塩素化
芳香族炭化水素等の従来これらの反応で使用され
ている溶媒を使用することが出来る。
本発明で使用するリン酸ジ又はモノエステル化
合物は当然酸性根を有し、それは酸としての水素
イオン、塩の形となつたナトリウム、カリウム等
のアルカリ金属塩、マグネシウム、カルシウム、
ストロンチウム、バリウム、マンガン、鉄、コバ
ルト、ニツケル、亜鉛、アルミニウム、錫等の二
価以上の多価金属塩；アンモニウム塩；メチル
−、エチル−、プロピル−、ブチル−、ヘキシル
−、オクチル−、ドデシル−、オクタデシル−、
オレイル−、ジエチル−、ジブチル−、ジステア
リル−、トリエチル−、トリブチル−、ジメチル
オクチル−、ジメチルデシル−、ジメチルドデシ
ル−、ジメチルテトラデシル−、ジメチルヘキサ
デシル−、ジメチルオクタデシル−、ジメチルオ
レイル−、ジラウリルモノメチル−、トリオクチ
ル−アミン、ジメチルアニリン；エチレンジアミ
ン、プロピレンジアミン、ヘキサメチレンジアミ
ン、ステアリルプロピレンジアミン等の炭素数１
〜30の第一級、第二級、第三級のモノ−及びポリ
アミン塩、オクタデシルトリメチルアンモニウ
ム、ジオクタデシルジメチルアンモニウム等の第
四級アンモニウム塩及びエタノールアミン、ジエ
タノールアミン、トリエタノールアミン、ジメチ
ルエタノールアミン、ジエチルエタノールアミ
ン、プロパノールアミン、ジプロパノールアミ
ン、前記の高級脂肪族アミンにエチレンオキサイ
ドを付加したアルカノールアミン等のアルカノー
ルアミン塩等が挙げられ、単独又は混合して使用
することが出来る。又、高級脂肪族アミン、アン
モニウム類としては、原料とした天然油脂に起因
する炭素数或は飽和度の異なるアミン類の混合物
であるものもそのまま使用することが出来る。
疎水性基とのバランスによるが、上記の塩類の
うち、アルカリ金属塩、アンモニウム塩、低級ア
ミン塩、低級アルカノールアミン塩等は親水性を
示し、水溶性乃至水分散性を示すものであり、使
用に際しては水溶性乃至水分散液での使用が可能
である。
又、二価以上の多価金属塩や高級アミン塩等は
疎水性で親油性を示し、顔料等の基材の表面の疎
水性化乃至油性化剤として単独又は溶剤溶液とし
て使用することも出来る。
又、勿論、酸の形或は前者の水溶液乃至水分散
液で予め顔料等の基材を処理した後、多価金属の
化合物乃至高級アミン化合物等を反応させて後者
の疎水性化合物乃至油性化合物とし、顔料等の基
材を処理することにも使用することが出来る。
次に本発明の顔料組成物を更に詳細に説明する
と、本発明において使用される顔料は、従来公知
の有機顔料、無機顔料、体質顔料等全て使用する
ことが出来る。
例えば、有機顔料としては、フタロシアニン
系、アゾ系、縮合アゾ系、アンスラキノン系、ペ
ノリン・ペリレン系、インジゴ・チオインジゴ
系、イソインドリノン系、アゾメチンアゾ系、ジ
オキサジン系、キナクリドン系、アニリンブラツ
ク系、トリフエニルメタン系及びカーボンブラツ
ク等であり、無機顔料系としては、酸化チタン
系、酸化鉄系、水酸化鉄系、酸化クロム系、スピ
ンネル型焼成顔料、クロム酸鉛系、クロム酸バー
ミリオン系、紺青系、アルミニウム粉末、ブロン
ズ粉末等、体質顔料としては、炭酸カルシウム
系、硫酸バリウム系、酸化珪素系、水酸化アルミ
ニウム系等が挙げられる。
本発明において、これらの顔料は乾燥微粉末状
の他、水性濾過ケーキ或は水性懸濁液の状態でも
使用することが出来る。
本発明で使用するリン酸エステル化合物は、単
独又は場合により、各用途に合せて従来公知の適
当な有機溶剤、塗料用ベヒクル、印刷インキ用ワ
ニス、コーテイング剤用ベヒクル等の固着剤樹
脂、熱可塑性樹脂、熱硬化性樹脂、可塑剤、架橋
剤、触媒等から選ばれた材料と共に使用すること
が出来る。
本発明の顔料組成物は、顔料と分散剤たるリン
酸エステル化合物、更には上記した材料と共に、
水性系で処理する方法、水性系で処理後油性に変
換する方法、油性乃至溶剤系にて処理する方法等
において、各種の分散機を用いて製造することが
出来る。
例えば、ボールミル、サンドミル、アトライタ
ー、横型連続媒体分散機、二本ロール、三本ロー
ル、加圧ニーダー、バンバリミキサー、エクスト
ルーダー等の従来公知の分散機により混合し混練
摩砕する方法が代表的な方法である。
又、顔料が水性濾過ケーキ或は水性懸濁液の状
態で得られる場合には、本発明で使用する疎水性
の分散剤を単独又は疎水性溶媒或は更に前記した
固着剤樹脂等と共にニーダー、フラツシヤー等に
てフラツシング法により顔料を水相から油相媒体
に容易に効率よく移行させることが出来る。
本発明におけるリン酸エステル化合物の使用量
は、顔料100重量部当り約１〜300重量部、好まし
くは約３〜約150重量部である。
本発明の顔料組成物は、それ自体、塗料、印刷
インキ、着色コーテイング剤、樹脂着色剤等の各
用途に合せた着色剤として使用される組成物であ
る場合の他、顔料を高濃度に含有する高顔料分散
体としても使用することが出来る。
塗料としては、従来公知の顔料が使用されてい
る塗料が全て含まれ、例えば、自動車塗料、建築
用塗料、木材用塗料、車両・機器用塗料、家庭塗
料、プラスチツク用塗料、プレコートメタル用塗
料、缶用塗料、船舶用塗料、防食塗料、光硬化塗
料、電子線硬化塗料、静電粉体塗料、ビニルゾル
塗料等が挙げられる。
又、印刷インキとしては従来公知の印刷インキ
が全て含まれ、例えば、凸版インキ、平版イン
キ、凹版のグラビアインキ、孔版のスクリーイン
キ、新聞インキ、フレキソインキ等が挙げられ
る。
塗料、印刷インキ、着色コーテイング剤等の場
合の顔料分が約0.1〜20重量％であるに対して、
高顔料含有分散体の場合は、約20〜70重量％、更
に溶媒を使用して処理した後乾燥させた易分散性
顔料の場合には約60〜95重量％の範囲で製造さ
れ、且つ使用される。
これら本発明で使用するリン酸エステル化合物
を分散剤として使用することは、顔料の合成時、
合成直後の段階、濾過等の後処理を行つた後、更
には乾燥・粉砕を行つた後、混練、分散を行う時
に添加使用することが出来る。
又、使用量も上記の段階で全量使用してもよい
し、製造工程、例えば、合成直後と分散時の如く
各段階に分けて分割添加することも優れた方法で
ある。
前記した如く、各用途に応じて従来公知の材料
が併せて使用されるが、媒体としては水或は水−
親水性溶媒系又は有機溶媒が使用され、有機溶媒
としては脂肪族系、脂環族系、芳香族系炭化水
素、ハロゲン化炭化水素系、エステル系、ケトン
系、グリコールエーテル系、アルコール系等が使
用され、特に限定されるものではない。
又、塗料用ビヒクル、印刷インキ用ワニス、コ
ーテイング剤用ベヒクル等としては、各用途に応
じて従来公知の油性乃至水性系のベヒクル材料を
使用することが出来る。例えば、長油長、中油
長、短油長のアルキツド樹脂、フエノール変性、
スチレン化アルキツド等の変性アルキツド樹脂、
アミノアルキツド樹脂、オイルフリーアルキツド
樹脂、焼付用アクリル樹脂、アクリルラツカー樹
脂、アクリルポリオール樹脂、ポリエステル樹
脂、エポキシ樹脂、ブチル化メラミン樹脂、メチ
ル化メラミン樹脂、尿素−メラミン樹脂、フエノ
ール樹脂、ロジン変性フエノール樹脂、ロジン変
性マレイン酸樹脂、フエノール変性マレイン酸樹
脂、ポリウレタン樹脂、スチレン樹脂、スチレン
アクリル樹脂、スチレン−ジエン共重合体、塩化
ビニル系共重合体、酢酸ビニル樹脂、酢酸ビニル
系共重合体、エチレン−酢酸ビニル樹脂、ブチラ
ール樹脂、石油樹脂、ロジンエステル、マレイン
化ロジンエステル等の変性樹脂、乾性油、ボイル
油等が挙げられる。
熱可塑性樹脂としては、ポリ塩化ビニル樹脂、
スチレン樹脂、アクリロニトリル−スチレン樹
脂、アクリル樹脂、メタクリル−スチレン樹脂、
ポリエステル樹脂が挙げられる。
可塑剤としては、フタル酸エステル、アジピン
酸エステル、セバシン酸エステル、ポリエステル
可塑剤、エポキシ化大豆油等が挙げられる。
又、必要に応じ、従来公知の顔料の分散剤或は
フラツシング助剤等を添加して併用することも本
発明の目的達成を妨げない。例えば、高級脂肪族
モノアミンや高級脂肪族ジアミン或はそれらの酢
酸塩や高級脂肪族塩等が挙げられる。
（作用・効果）
本発明で使用するポリエステル鎖が結合したリ
ン酸エステル化合物は、顔料、塗料、印刷イン
キ、プラスチツク着色剤等の色材分野において、
前記した天然リン脂質のレシチンに見られるが如
き酸化や酸敗による変質或いは腐敗の虞のない、
安定性に優れた表面改質や、媒体への再分散等に
優れた効果を有する。
本発明で使用するポリエステル鎖を結合したリ
ン酸エステル化合物は、その有するリン酸エステ
ル結合やエステル結合の電荷的吸引性、炭化水素
鎖の親媒性等の作用により顔料の表面に吸着して
媒体への湿潤性を向上させ、分散剤として媒体へ
の分散性及び流動性を良好にし、水性濾過ケーキ
等からのフラツシング助剤としても顔料の表面を
親油性若しくは疎水性に処理し、容易に効率良
く、フラツシングすることが出来る。
（参考例・実施例）
次に参考例（リン酸ジ又はモノエステル化合物
の製造例）及び実施例を挙げて本発明を更に具体
的に説明する。尚、文中、部又は％とあるのは特
に断りのない限り重量基準である。
参考例 １
(1) 12−ヒドロキシステアリン酸の自己縮合ポリ
エステルの合成及びそのメチルエステル化反
応。
攪拌機、温度計、水分計付逆流コンデンサー
及び投入口を有する四ツ口のガラス製反応器及
びオイルバスを準備した。
そこへ12−ヒドロキシステアリン酸100部及
びトルエン100部を仕込み、攪拌して溶解させ
た。溶解後昇温させ、縮合触媒としてｐ−トル
エンスルホン酸1.0部を添加した。反応液を120
℃に昇温し、12−ヒドロキシステアリン酸の自
己縮合ポリエステル化反応を進行させた。60
分、120分及び180分間と溜出水分量及び反応物
の赤外吸収スペクトルによつて反応の進行を調
べ、200分で冷却しポリエステル化反応を終了
した。
次いで63℃になつたところで、メタノール50
部、酢酸メチル100部及びｐ−トルエンスルホ
ン酸0.5部加え、110℃に昇温し、溶媒を溜出さ
せながらメチルエステル化反応を進めた。150
部溜出したところで63℃に温度を下げ、メタノ
ール200部を加え、110℃に昇温し、溶媒を溜去
した。溜去量は245部であつた。
メチルエステル化反応については約５時間要
した。反応後、300部の水を加えて水溶分を抽
出し二層に別れた油層分を取出した。脱水する
為、油層分にトルエン150部及びメタノール200
部を加えて窒素ガスを吹込みながら130℃まで
昇温し溶媒を溜去した。溜出量は345部であつ
た。
得られた反応生成物はこはく色の液状物であ
り、それが12−ヒドロキシステアリン酸の自己
縮合ポリエステルのメチルエステルであること
は赤外吸収スペクトル及びゲルパーミエーシヨ
ンクロマトグラフの分析データにて確認した。
反応生成物の酸価の測定からポリマーのメチ
ルエステル化反応はほぼ完結していることが確
認された。又、反応生成物のヒドロキシル化の
測定値は40.8であつた。このことからこの12−
ヒドロキシステアリン酸の自己縮合ポリエステ
ルのメチルエステルの１グラム当量は1375であ
り、それからの平均縮合重合度はおおよそ５で
ある。
(2) 12−ヒドロキシステアリン酸の自己縮合ポリ
エステルのメチルエステルのリン酸ジエステル
化合物の合成反応、
攪拌機、温度計、滴下ロート及び逆流コンデ
ンサーを有する四ツ口のガラス製反応器及びウ
オーターバスを準備した。
逆流コンデンサーには、発生する塩酸ガス除
去用ガラス管を付け、これに安全瓶及び塩酸ガ
ス吸収瓶を連絡し、更に水銀減圧計に連結し、
真空ポンプに連絡した。
反応器に7.0部のオキシ塩化リンを入れた。
別に上記(1)で得た12−ヒドロキシステアリン
酸の自己縮合ポリエステルのメチルエステル
（１グラム当量は1375）62.8部及びベンゼン
62.8部を混合溶解し、滴下ロートに仕込んで反
応器に装填した。
反応器を氷及び水で外部から冷却しながら上
記の12−ヒドロキシステアリン酸のポリエステ
ルのメチルエステルのベンゼン溶液を５〜10℃
で、特に温度10℃以上に上がらない様に注意し
ながら滴下する。添加終了後、10℃で１時間か
きまぜ、反応温度を上昇させながら反応器内を
徐々に減圧にし、反応により生成する塩酸ガス
を吸収瓶中の水酸化ナトリウム水溶液に吸収さ
せる。約５時間を要して温度を約40℃、真空度
100mmHgとし塩酸ガスの発生が認められなくな
つた後冷却する。
この状態ではリン酸（ポリ12−ヒドロキシス
テアリン酸のメチルエステル）モノエステル・
ジクロライドが発生している。次いで上記のポ
リ（12−ヒドロキシステアリン酸）のメチルエ
ステル62.8部、ベンゼン62.8部及びトリエチル
アミン4.62部を混合溶解し、滴下ロートに仕込
んで10〜20℃にて60分間を要して滴下し反応さ
せ、２時間攪拌し、更に２時間かけて40℃に昇
温し、２時間攪拌し、冷却した。
上記において、水酸基を有するポリエステ
ル、オキシ塩化リン及びトリエチルアミンの当
量比は２：３：１である。
次いで、反応生成液からリン酸エステルクロ
ライドの脱塩素反応（加水分解）及び除去又は
トリエチルアミン塩酸塩除去の為、水、希水酸
化ナトリウム水、希塩酸酸性水及び水にて洗浄
した。洗浄したベンゼン相を硫酸ナトリウムで
乾燥した後、ベンゼンを減圧下で溜去し、茶色
の液状の反応生成物を得た。
上記反応生成物は赤外吸収スペクトル及びゲ
ルパーミエーシヨンクロマトグラフの分析チヤ
ートによつて、12−ヒドロキシステアリン酸の
自己縮合ポリエステルのメチルエステルのリン
酸ジエステル化合物を主成分とするもの（分散
剤１）であることが確認された。主成分の平均
分子量は約2500〜2800であつた。
参考例 ２〜11
参考例１の(2)の資材に代えて、後記第１表に記
載の資材を使用し、参考例１の(2)と同様にして各
種のリン酸エステル化合物を得た。
参考例 12
参考例１の(2)で使用した攪拌機、温度計、滴下
ロート、逆流コンデンサー、減圧系及び塩酸ガス
吸収系の付いた四つ口のガラス製反応器に70部の
オキシ塩化リンを仕込んだ。
別に参考例１の(1)と同様にして合成したポリ12
−ヒドロキシステアリン酸のメチルエステル（平
均分子量1440）65.8部をベンゼン65.8部に混合溶
解し、滴下ロートに仕込み、参考例１の(2)と同様
にして反応させて、リン酸（ポリ12−ヒドロキシ
ステアリン酸のメチルエステル）モノエステル・
ジクロラドを生成させ、次いで参考例１の(1)と同
様にして合成したポリ12−ヒドロキシステアリン
酸のメチルエステル（平均分子量600）27.4部を
ベンゼン27.4部及びトリエチルアミン4.62部と混
合溶解し、参考例１の(2)と同様に反応させた。
上記において、平均分子量1440ポリエステルア
ルコール、平均分子量600のポリエステルアルコ
ール、オキシ塩化リン及びトリエチルアミンの当
量比は、１：１：３：１である。
冷却した反応生成液を参考例１の(2)と同様にし
て、脱塩素反応（加水分解）、洗浄、精製、乾燥、
濃縮及び脱溶剤して茶色の液状の反応生成物を得
た。
参考例１の(2)と同様に分析して、ポリ12−ヒド
ロキシステアリン酸のメチルエステルのリン酸ジ
エステルを主成分とするもの（分散剤12）であ
り、その主成分の平均分子量は約1900〜2100であ
る事が確認された。
参考例 13〜20
参考例12の資材に代えて後記第２表に記載の資
材を使用し、参考例12と同様にして各種のリン酸
エステル化合物を得た。
実施例 １
銅フタロシアニンブルー顔料（C.I.ピグメント
ブルー15−３）水性濾過ケーキ（顔料含有率42
％）238部を、フラツシヤーに仕込んだ。別に、
参考例１で得られた分散剤１のリン酸根をほぼ等
しい当量のロジンアミンにて中和し、塩を作つ
た。このロジンアミン塩60部を石油系インキソル
ベント40部に溶解して添加し、常法に従いながら
混練し、フラツシングを行つた。
従来公知のフラツシング助剤に比べ非常に容易
にケーキの水分が遊離し、銅フタロシアニンブル
ー顔料は油性の該分散剤に移行した。
更に水分を完全に除去し、銅フタロシアニンブ
ルー顔料を含むフラツシユドカラーが得られた。
上記で得られた銅フタロシアニンブルー顔料を含
むフラツシユドカラーを用いてオフセツト平板印
刷インキを調製した。
上記で得た銅フタロシアニンブルー顔料のフラ
ツシドカラー（純分50％） 38.0部
オフセツト片版インキ用調合ワニス 60.0部
５％コバルトドライヤー 0.2部
８％マンガンドライヤー 1.0部インキソルベント 0.8部
合 計 100部
上記において、オフセツト平版インキ用調合ワ
ニスは下記の配合のものである。
ロジン変性フエノール樹脂 35部
乾性油 25部
乾性油変性イソフタル酸アルキツド 10部
インキソルベント 29.5部アルミニウムキレート 0.5部
合 計 100部
上記で得た銅フタロシアニンブルー顔料インキ
を藍色インキとしてオフセツト印刷機にて上質紙
に印刷し、鮮明な藍色の印刷物を得た。
又、前記の銅フタロシアニンブルー顔料の水性
濾過ケーキに代えて、ジスアゾイエロー顔料（C.
I.ピグメントイエロー12）の水性濾過ケーキ（顔
料含有率27％）、ブリリアントカーミン6B顔料
（C.I.ピグメントレツド57−１）の水性濾過ケー
キ（顔料含有率25％）を用いて上記と同様にして
フラツシユドカラーを作り、次いで各々黄色及び
紅色のオフセツト平版インキを調製した。
同様にしてレーキツドＣ顔料（C.I.ピグメント
レツド53−１）の水性濾過ケーキからフラツシユ
ドカラーを得、オフセツト平版用金赤インキを得
た。又、銅フタロシアニンブルー顔料（C.I.ピグ
メントグリーン７）の水性濾過ケーキからフラツ
シユドカラーを得、、オフセツト平版用草インキ
を得た。
夫々フラツシングにおいては水の分離が容易で
あり、優れた油相への移行を示し、オフセツト平
版印刷においては鮮明で優れた印刷物が得られ
た。
又、上記において使用した分散剤１に代えて分
散剤２〜分散剤20を使用し、上記と同様に優れた
効果が得られた。
又、上記において分散剤のリン酸根を中和した
ロジンアミンに代えて、ココナツトアミン又は牛
脂プロピレンジアミン又はカルシウム、ストロン
チウム又はアルミニウムの水酸化物にて中和して
得た分散剤の塩を使用し、上記と同様に優れた効
果が得られた。
実施例 ２
カーボンブラツク顔料 20部
参考例１で得られた分散剤１の牛脂プロピレンジ
アミン塩 ６部オフセツト平版インキ用調合ワニス 69部
合 計 95部
の配合にて三本ロールでカーボンブラツク顔料を
混練及び分散した。カーボンブラツク顔料はワニ
ス中に非常に良く分散した。
上記で得たカーボンブラツク顔料のワニス分散
物 95部
５％コバルトドライヤー 0.2部
８％マンガンドライヤー 1.0部イソキソルベント 3.8部
合 計 100部
にて充分均一に混合及び混練し、カーボンブラツ
クインキを得た。これを用いてオフセツト印刷機
にて印刷し、黒度の高い墨色の印刷物を得た。
又、上記において使用した分散剤１に代えて分
散剤２〜分散剤20を使用し上記と同様優れた効果
が得られた。
又、上記において分散剤のリン酸根を中和した
牛脂プロピレンジアミンに代えて、ロジンアミ
ン、ココナツトアミン又はココナツトプロピレン
ジアミン又はカルシウム、ストロンチウム又はア
ルミニウムの水酸化物にて中和して得た分散剤の
塩を使用し、上記と同様に優れた効果が得られ
た。
又、実施例で得られた黄色インキ、紅色インキ
及び藍色インキに、上記で得た墨インキを加え
て、オフセツト平版用プロセス黄インキ、プロセ
ス紅インキ、プロセス藍インキ、プロセス墨イン
キとして四色プロセス印刷を行い、鮮明で美麗な
多色刷り印刷物が得られた。
実施例 ３
実施例１で得られた銅フタロシアニンブルー顔
料のフラツシユドカラー（純分50％） 10.8部
ルチル型チタン白 2.0部
速乾性スチレン化アルキツド樹脂 72.6部
キシロール 6.6部
ミネラルスピリツド 7.6部
６％ナフテン酸コバルト 0.3部皮張り防止剤 0.1部
合 計 100部
の処方にて充分均一に混合及び分散し、機械、車
輛等の金属材料用の常温乾燥型の青色の速乾エナ
メルを得た。塗布したところ鮮明で美麗な塗装が
行われた。
次に、実施例１の銅フタロシアニンブルー顔料
に代えて、ジスアゾイエロー（C.I.ピグメントイ
エロー14）、４−アミノフタルイミドをジアゾ化
してアセトアセトアニライドとカツプリングした
フアーストイエロー系顔料、ウオツチングレツド
（C.I.ピグメントレツド48）、カーミンFB（C.I.ピ
グメントレツド３）の顔料の水性濾過ケーキを使
用して実施例１と同様にしてフラツシングを行
い、各々の顔料のフラツシユドカラーを得た。
これらは上記塗料の組成において銅フタロシア
ニン顔料に代えて使用し、各々の色の塗料が得ら
れ、鮮明で美麗な塗布板が得られた。
実施例 ４
銅フタロシアニンブルー顔料（C.I.ピグメントブ
ルー15−３）の乾燥粉砕顔料 10部
参考例１で得られた分散剤１の酸根をほぼ等しい
当量のトリエチルアミンで中和した塩 ２部
キシロール 13部ブタノール ５部
合 計 30部
にて連続式横型媒体分散機にて分散させ、銅フタ
ロシアニンブルー顔料のキシロールブタノール混
合溶媒の分散液が得られた。
次いで以下の処方で塗料を調製した。
上記で得た銅フタロシアニンブルー及び分散剤１
の塩を含む溶媒分散液 ３部
ルチル型チタン白 14部
熱可塑性アクリル樹脂 70部
トルオール 6.8部
キシロール 3.2部
ブタノール 2.2部セロソルブ 0.8部
合 計 100部
これを、自動車用アクリルラツカーエナメルと
して使用して塗布し、鮮明で美麗な塗装が得られ
た。
又、上記において使用した分散剤１に代えて分
散剤２〜分散剤20を使用し、上記と同様優れた塗
料が得られた。
又、上記において分散剤のリン酸根を中和した
トリエチルアミンに代えて、ロジンアミン、ココ
ナツトアミン、牛脂プロピレンジアミン又はココ
ナツトプロピレンジアミン又はカルシウム、スト
ロンチウム又はアルミニウムの水酸化物にて中和
して得た分散剤の塩を使用し、上記と同様に優れ
た効果が得られた。
(Industrial Application Field) The present invention relates to a new pigment composition, and more specifically, the present invention relates to a new pigment composition, and more specifically, it is used for coloring paints, printing inks, synthetic resins, etc., using a phosphoric acid ester compound containing a polyester chain as a dispersant or flushing aid. The purpose of the present invention is to provide a pigment composition useful as a pigment composition. (Prior Art) Conventionally, in the production of paints and printing inks, dispersants or For example, the phospholipid lecithin has been used as a flushing aid. (Problems to be solved by the invention) However, since lecithin is a natural phospholipid, it is susceptible to oxidation and rancidity, and there is a risk of deterioration and putrefaction.However, lecithin is a dispersing agent that has stable and excellent properties. There was a need for a compound that could also be used as a flushing aid. In view of the above-mentioned deficiencies in pigment dispersants or flushing aids, the present inventors have conducted various studies on compounds that have an affinity for various vehicles and varnishes, and also have an affinity for pigments. The present invention was completed based on the discovery that a phosphoric acid ester compound obtained by reacting a polyester having a hydroxyl group with phosphoric acid exhibits excellent properties and effects. (Means for Solving the Problems) That is, the present invention provides a pigment composition containing a pigment and a dispersant, wherein the dispersant is a phosphoric acid ester compound represented by the following general formula or an ammonium salt thereof, The pigment composition is characterized by being a primary to tertiary organic amine salt, an organic quaternary ammonium salt, or a monovalent to trivalent metal salt. [However, R 1 is a hydrocarbon group having 4 to 30 carbon atoms.
R2 is R3OOC - R1 [-O.OC- R1 ] -o , a hydrogen atom, or a hydrocarbon group having 1 to 30 carbon atoms. R 3 is a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms. n
is a value of 1 or more and the molecular weight is 10,000 or less. ] (Preferred Embodiment) To explain the present invention in detail, the dispersant used in the present invention and which mainly characterizes the present invention is a specific phosphoric ester compound as defined above. The phosphoric acid ester compound used in the present invention can be obtained by reacting 1 mol or 2 mol of a polyester alcohol component as an essential component with 1 mol of a phosphorylating agent according to a conventionally known method. As the phosphorylating agent, conventionally known phosphorus oxychloride, phosphorus pentoxide, phosphorus trichloride, phosphoric anhydride, acetyl phosphoric acid, etc. are used. Phosphorous oxychloride is the most preferred phosphorylating agent. Regarding reaction conditions, in the case of phosphorus oxychloride, the initial esterification reaction is intense, so it is preferable to carry out the reaction at a low temperature.To accelerate the reaction, it is also possible to reduce the pressure in the reactor to remove the generated hydrogen chloride. . It is also preferable to heat the reaction to complete the reaction. After the reaction is complete, remove unreacted chloride with hot water,
Wash with cold water and hydrolyze. In addition, when using a halogenated phosphorus compound, it is also preferable to use a basic catalyst, for example, tertiary amines such as triethylamine, pyridine, 2,6-lutidine, 1,8-diaza-bicyclo(5, 4,0) Organic bases such as undecene-7, manifest or latent inorganic bases such as oxides, hydroxides, carbonates, organic acid salts of alkali metals and alkaline earth metals can be used, and after the reaction It is preferable to remove halides, salts, bases and other impurities by filtration, neutralization, washing with water, etc. The polyester alcohol component to be reacted is selected and used depending on the purpose of the product. The phosphoric acid ester compound used in the present invention can be obtained by directly reacting a polyester alcohol component, etc. that matches the target compound with a phosphorylating agent, or by reacting it with, for example, methyl ester of 12-hydroxystearic acid in advance. Then, the methyl ester is hydrolyzed, and it is condensed with a polyester of 12-hydroxystearic acid or other alcohols by a demethanol reaction. It can also be obtained by a method such as synthesizing a phosphoric acid di- or monoester compound of polyester. The polyester alcohol component used is a conventionally known aliphatic, alicyclic or aromatic carboxylic acid having a hydroxyl group or a polyester thereof. The molecular weight of the polyester alcohol component used is not particularly limited, but
Average molecular weight of about 10,000 or less, preferably about 500 to about
It is 5000. As such a polyester alcohol component, for example, the following are used. (A) Self-condensing polyesters of hydroxycarboxylic acids, preferably polyesters of hydroxycarboxylic acids containing a hydrocarbon chain having 4 to 30 carbon atoms. For example, ricinoleic acid, ricinoleic acid, 12
-Hydroxystearic acid, castor oil fatty acid,
Hydrogenated castor oil fatty acid, δ-hydroxyvaleric acid,
Examples include one or more self-condensing polyesters selected from hydroxycarboxylic acids such as ε-hydroxycaproic acid, p-hydroxyethyloxybenzoic acid, and 2-hydroxynaphthalene-6-carboxylic acid. (B) An esterified product of the carboxylic acid at the other end of the polyester alcohol component described in (A) above. These are esters with aliphatic, alicyclic or aromatic alcohols having 1 to 30 carbon atoms, such as methyl-, ethyl-,
Examples include esters such as propyl, butyl, hexyl, octyl, dodecyl, hexadecyl, octadecyl, cyclohexyl, and benzyl alcohol. In addition to the phosphoric diester compound of the polyester alcohol component described above, the phosphoric acid ester compound used in the present invention limits the reaction between the polyester alcohol component and the phosphorylating agent to a monoester, and converts other monoester components into monoesters. It also includes asymmetric phosphodiester compounds esterified using hydroxycarboxylic acids, alcohol esters of hydroxycarboxylic acids, or alcohols, and can be synthesized according to conventional methods for synthesizing asymmetric phosphodiester compounds. Conventionally known alcohol components are used. For example, hydroxycarboxylic acids and alcohol esters thereof include ricinoleic acid,
12-hydroxystearic acid, γ-hydroxybutyric acid, δ-hydroxyvaleric acid, ε-hydroxycaproic acid, p-hydroxyethyloxybenzoic acid,
These are esters of 2-hydroxynaphthalene-6-carboxylic acid and the like and alcohols having 1 to 30 carbon atoms, and the alcohols include alcohols having 1 to 30 carbon atoms, such as methyl alcohol,
Ethyl alcohol, propyl alcohol, butyl alcohol, hexyl alcohol, octyl alcohol, decyl alcohol, dodecyl alcohol, tridecyl alcohol, hexadecyl alcohol, octadecyl alcohol, tetracosyl alcohol, hexacosyl alcohol, octadecenyl alcohol, cyclohexyl alcohol , benzyl alcohol and the like. In the phosphoric acid esterification reaction of an alcohol component containing polyester alcohol as an essential component using the above-mentioned present invention, it is inert to these raw materials and products, and dissolves these raw materials, etc. It is also preferred to use organic solvents. For example, aliphatic saturated hydrocarbons such as octane, petroleum ether, ligroin, mineral spirits, kerosene, aromatic hydrocarbons such as benzene, toluene, xylene, halogenated aliphatic hydrocarbons such as trichloroethane, tetrachloroethane, etc. - Solvents conventionally used in these reactions, such as chlorinated aromatic hydrocarbons such as dichlorobenzene and trichlorobenzene, can be used. The phosphoric acid di- or monoester compound used in the present invention naturally has an acidic radical, which includes hydrogen ions as acids, alkali metal salts such as sodium and potassium in the form of salts, magnesium, calcium, etc.
Salts of divalent or higher polyvalent metals such as strontium, barium, manganese, iron, cobalt, nickel, zinc, aluminum, tin; ammonium salts; methyl, ethyl, propyl, butyl, hexyl, octyl, dodecyl -, octadecyl-,
Oleyl, diethyl, dibutyl, distearyl, triethyl, tributyl, dimethyloctyl, dimethyldecyl, dimethyldodecyl, dimethyltetradecyl, dimethylhexadecyl, dimethyloctadecyl, dimethyloleyl, Lauryl monomethyl, trioctylamine, dimethylaniline; carbon number 1 such as ethylene diamine, propylene diamine, hexamethylene diamine, stearyl propylene diamine, etc.
~30 primary, secondary, and tertiary mono- and polyamine salts, quaternary ammonium salts such as octadecyltrimethylammonium, dioctadecyldimethylammonium, and ethanolamine, diethanolamine, triethanolamine, dimethylethanolamine, Examples include alkanolamine salts such as diethylethanolamine, propanolamine, dipropanolamine, and alkanolamines obtained by adding ethylene oxide to the above-mentioned higher aliphatic amines, which can be used alone or in combination. Further, as the higher aliphatic amines and ammoniums, amines which are mixtures of amines having different carbon numbers or degrees of saturation derived from the natural oils and fats used as raw materials can also be used as they are. Depending on the balance with the hydrophobic group, among the above salts, alkali metal salts, ammonium salts, lower amine salts, lower alkanolamine salts, etc. exhibit hydrophilicity and are water-soluble or water-dispersible, and are used. In this case, it can be used in a water-soluble or aqueous dispersion. In addition, polyvalent metal salts of divalent or higher valence, higher amine salts, etc. are hydrophobic and lipophilic, and can be used alone or as a solvent solution as agents for making the surface of base materials such as pigments hydrophobic or oily. . Of course, after treating a base material such as a pigment in advance with an acid form or an aqueous solution or dispersion of the former, a polyvalent metal compound or a higher amine compound is reacted to form a hydrophobic compound or an oily compound of the latter. It can also be used to treat base materials such as pigments. Next, the pigment composition of the present invention will be explained in more detail. As the pigment used in the present invention, all conventionally known organic pigments, inorganic pigments, extender pigments, etc. can be used. For example, organic pigments include phthalocyanine, azo, condensed azo, anthraquinone, penolin/perylene, indigo/thioindigo, isoindolinone, azomethine azo, dioxazine, quinacridone, aniline black, and trifluoride. Inorganic pigments include titanium oxide, iron oxide, iron hydroxide, chromium oxide, spinel fired pigments, lead chromate, vermilion chromate, and navy blue. Examples of extender pigments include calcium carbonate, barium sulfate, silicon oxide, and aluminum hydroxide. In the present invention, these pigments can be used not only in the form of dry fine powder but also in the form of an aqueous filter cake or an aqueous suspension. The phosphoric acid ester compound used in the present invention may be used alone or in accordance with each application with a conventionally known suitable organic solvent, a fixing agent resin such as a vehicle for paint, a varnish for printing ink, a vehicle for coating agent, or a thermoplastic. It can be used with materials selected from resins, thermosetting resins, plasticizers, crosslinking agents, catalysts, etc. The pigment composition of the present invention comprises a pigment, a phosphoric acid ester compound as a dispersant, and the above-mentioned materials.
Various types of dispersion machines can be used for production, such as a method of processing in an aqueous system, a method of converting the aqueous system to an oil-based one after treatment, and a method of processing in an oil-based or solvent system. For example, a typical method is mixing, kneading, and grinding using a conventionally known dispersing machine such as a ball mill, sand mill, attritor, horizontal continuous media dispersing machine, two rolls, three rolls, pressure kneader, Banbury mixer, and extruder. This is a great method. In addition, when the pigment is obtained in the form of an aqueous filter cake or an aqueous suspension, the hydrophobic dispersant used in the present invention may be used alone or together with a hydrophobic solvent or the above-mentioned fixing agent resin etc. in a kneader, The pigment can be easily and efficiently transferred from the aqueous phase to the oil phase medium by a flushing method using a flusher or the like. The amount of the phosphoric acid ester compound used in the present invention is about 1 to 300 parts by weight, preferably about 3 to about 150 parts by weight, per 100 parts by weight of the pigment. The pigment composition of the present invention can be used as a coloring agent for various uses such as paints, printing inks, colored coating agents, resin colorants, etc. It can also be used as a high pigment dispersion. Paints include all paints that use conventionally known pigments, such as automotive paints, architectural paints, wood paints, vehicle and equipment paints, household paints, plastic paints, pre-coated metal paints, Examples include can paints, marine paints, anticorrosion paints, photo-curable paints, electron beam-curable paints, electrostatic powder paints, vinyl sol paints, and the like. The printing ink includes all conventionally known printing inks, such as letterpress ink, lithographic ink, gravure ink for intaglio, screen ink for stencil printing, newspaper ink, and flexo ink. While the pigment content in paints, printing inks, colored coating agents, etc. is approximately 0.1 to 20% by weight,
In the case of high pigment content dispersions, it is produced and used in the range of about 20 to 70% by weight, and in the case of easily dispersible pigments treated with a solvent and then dried, in the range of about 60 to 95% by weight. be done. The use of these phosphoric acid ester compounds used in the present invention as a dispersant means that during pigment synthesis,
It can be added and used immediately after synthesis, after post-treatment such as filtration, after drying and pulverization, and during kneading and dispersion. Further, the amount to be used may be used in its entirety at the above-mentioned stage, or it is also an excellent method to add it in portions at each stage of the manufacturing process, for example, immediately after synthesis and at the time of dispersion. As mentioned above, conventionally known materials are used in conjunction with each application, but the medium may be water or water.
Hydrophilic solvents or organic solvents are used, and organic solvents include aliphatic, alicyclic, aromatic hydrocarbons, halogenated hydrocarbons, esters, ketones, glycol ethers, alcohols, etc. used, and is not particularly limited. Furthermore, as the paint vehicle, printing ink varnish, coating agent vehicle, etc., conventionally known oil-based or water-based vehicle materials can be used depending on the purpose. For example, alkyd resins with long oil length, medium oil length, and short oil length, phenol modified resins,
Modified alkyd resins such as styrenated alkyds,
Amino alkyd resin, oil-free alkyd resin, acrylic resin for baking, acrylic lacquer resin, acrylic polyol resin, polyester resin, epoxy resin, butylated melamine resin, methylated melamine resin, urea-melamine resin, phenolic resin, rosin-modified phenol Resin, rosin modified maleic acid resin, phenol modified maleic acid resin, polyurethane resin, styrene resin, styrene acrylic resin, styrene-diene copolymer, vinyl chloride copolymer, vinyl acetate resin, vinyl acetate copolymer, ethylene - Modified resins such as vinyl acetate resin, butyral resin, petroleum resin, rosin ester, maleated rosin ester, drying oil, boiling oil and the like. Thermoplastic resins include polyvinyl chloride resin,
Styrene resin, acrylonitrile-styrene resin, acrylic resin, methacryl-styrene resin,
Examples include polyester resins. Examples of the plasticizer include phthalate ester, adipate ester, sebacate ester, polyester plasticizer, and epoxidized soybean oil. Further, if necessary, conventionally known pigment dispersants or flushing aids may be added and used in combination without hindering the achievement of the object of the present invention. Examples include higher aliphatic monoamines, higher aliphatic diamines, acetates and higher aliphatic salts thereof. (Actions/Effects) The phosphoric acid ester compound with bonded polyester chains used in the present invention is used in the field of color materials such as pigments, paints, printing inks, and plastic colorants.
There is no risk of deterioration or putrefaction due to oxidation or rancidity as seen in the natural phospholipid lecithin mentioned above.
It has excellent effects on surface modification with excellent stability and redispersion into media. The phosphoric acid ester compound used in the present invention, which has a polyester chain bonded thereto, adsorbs onto the surface of the pigment due to the charge-absorbing properties of its phosphoric acid ester bonds and ester bonds, and the hydrophilic properties of its hydrocarbon chains. As a dispersant, it improves dispersibility and fluidity in media, and as a flushing aid for aqueous filter cakes, etc., it treats the surface of pigments to be lipophilic or hydrophobic, making them easy to use and efficient. It can be flushed well. (Reference Examples/Examples) Next, the present invention will be described in more detail with reference to Reference Examples (manufacturing examples of phosphoric acid di- or monoester compounds) and Examples. In the text, parts or percentages are based on weight unless otherwise specified. Reference Example 1 (1) Synthesis of self-condensing polyester of 12-hydroxystearic acid and its methyl esterification reaction. A four-neck glass reactor with a stirrer, a thermometer, a backflow condenser with a moisture meter, and an inlet, and an oil bath were prepared. 100 parts of 12-hydroxystearic acid and 100 parts of toluene were charged therein and dissolved by stirring. After dissolution, the temperature was raised, and 1.0 part of p-toluenesulfonic acid was added as a condensation catalyst. 120% reaction solution
The temperature was raised to .degree. C., and the self-condensation polyesterification reaction of 12-hydroxystearic acid was allowed to proceed. 60
The progress of the reaction was checked by the amount of distilled water and the infrared absorption spectrum of the reactant at 200 minutes, 120 minutes, and 180 minutes, and the polyesterification reaction was completed by cooling at 200 minutes. Next, when the temperature reached 63℃, methanol was added at 50℃.
100 parts of methyl acetate and 0.5 parts of p-toluenesulfonic acid were added thereto, and the temperature was raised to 110°C to proceed with the methyl esterification reaction while distilling off the solvent. 150
After partially distilling, the temperature was lowered to 63°C, 200 parts of methanol was added, the temperature was raised to 110°C, and the solvent was distilled off. The amount distilled off was 245 parts. The methyl esterification reaction required about 5 hours. After the reaction, 300 parts of water was added to extract the water-soluble component, and the oil layer separated into two layers was taken out. To dehydrate, add 150 parts of toluene and 200 parts of methanol to the oil layer.
The mixture was heated to 130°C while blowing nitrogen gas, and the solvent was distilled off. The distillate amount was 345 parts. The reaction product obtained was an amber liquid, and it was confirmed by infrared absorption spectrum and gel permeation chromatography analysis data that it was a methyl ester of self-condensed polyester of 12-hydroxystearic acid. did. Measurement of the acid value of the reaction product confirmed that the methyl esterification reaction of the polymer was almost complete. The measured value of hydroxylation of the reaction product was 40.8. From this, this 12−
One gram equivalent of the methyl ester of the self-condensing polyester of hydroxystearic acid is 1375, and the average degree of condensation polymerization therefrom is approximately 5. (2) Synthesis reaction of phosphoric diester compound of methyl ester of self-condensed polyester of 12-hydroxystearic acid. A four-necked glass reactor equipped with a stirrer, thermometer, dropping funnel, and backflow condenser, and a water bath were prepared. . A glass tube for removing generated hydrochloric acid gas is attached to the backflow condenser, and a safety bottle and a hydrochloric acid gas absorption bottle are connected to this, and further connected to a mercury decompression gauge.
I contacted the vacuum pump. 7.0 parts of phosphorus oxychloride was charged to the reactor. Separately, 62.8 parts of methyl ester of self-condensed polyester of 12-hydroxystearic acid obtained in (1) above (1 gram equivalent is 1375) and benzene.
62.8 parts were mixed and dissolved, charged into a dropping funnel, and loaded into a reactor. While externally cooling the reactor with ice and water, the benzene solution of the above polyester methyl ester of 12-hydroxystearic acid was heated to 5-10°C.
Then, drop the solution while being careful not to let the temperature rise above 10℃. After the addition is complete, stir at 10°C for 1 hour, gradually reduce the pressure inside the reactor while increasing the reaction temperature, and absorb the hydrochloric acid gas produced by the reaction into the aqueous sodium hydroxide solution in the absorption bottle. It takes about 5 hours to raise the temperature to about 40℃ and the degree of vacuum.
Set the temperature to 100 mmHg and cool after no longer generating hydrochloric acid gas. In this state, phosphoric acid (methyl ester of poly12-hydroxystearic acid) monoester
Dichloride is generated. Next, 62.8 parts of the above methyl ester of poly(12-hydroxystearic acid), 62.8 parts of benzene, and 4.62 parts of triethylamine were mixed and dissolved, charged into a dropping funnel, and added dropwise over 60 minutes at 10 to 20°C to react. The mixture was stirred for 2 hours, heated to 40°C over a further 2 hours, stirred for 2 hours, and cooled. In the above, the equivalent ratio of the polyester having a hydroxyl group, phosphorus oxychloride, and triethylamine is 2:3:1. Next, in order to dechlorinate (hydrolyze) and remove phosphoric acid ester chloride or to remove triethylamine hydrochloride from the reaction product solution, it was washed with water, diluted sodium hydroxide solution, diluted hydrochloric acid acidified water, and water. After drying the washed benzene phase with sodium sulfate, benzene was distilled off under reduced pressure to obtain a brown liquid reaction product. The above reaction product was found to be mainly composed of a phosphoric diester compound of methyl ester of self-condensing polyester of 12-hydroxystearic acid (dispersing agent 1). ) was confirmed. The average molecular weight of the main components was about 2500-2800. Reference Examples 2 to 11 Various phosphate ester compounds were obtained in the same manner as in Reference Example 1 (2), using the materials listed in Table 1 below in place of the materials in Reference Example 1 (2). . Reference Example 12 70 parts of phosphorus oxychloride was added to the four-necked glass reactor equipped with the stirrer, thermometer, dropping funnel, backflow condenser, pressure reduction system, and hydrochloric acid gas absorption system used in Reference Example 1 (2). I prepared it. Separately, poly12 synthesized in the same manner as (1) of Reference Example 1
- 65.8 parts of methyl ester of hydroxystearic acid (average molecular weight 1440) was mixed and dissolved in 65.8 parts of benzene, charged into a dropping funnel, and reacted in the same manner as in Reference Example 1 (2). Stearic acid methyl ester) monoester
Dichlorad was produced, and then 27.4 parts of methyl ester of poly-12-hydroxystearic acid (average molecular weight 600) synthesized in the same manner as in Reference Example 1 (1) was mixed and dissolved with 27.4 parts of benzene and 4.62 parts of triethylamine to produce Reference Example. The reaction was carried out in the same manner as in (2) of 1. In the above, the equivalent ratio of polyester alcohol with an average molecular weight of 1440, polyester alcohol with an average molecular weight of 600, phosphorus oxychloride, and triethylamine is 1:1:3:1. The cooled reaction product liquid was subjected to dechlorination reaction (hydrolysis), washing, purification, drying, and treatment in the same manner as in (2) of Reference Example 1.
Concentration and solvent removal gave a brown liquid reaction product. Analyzing in the same manner as in Reference Example 1 (2), it was found that the main component was a phosphoric diester of methyl ester of poly-12-hydroxystearic acid (Dispersant 12), and the average molecular weight of the main component was approximately 1900. ~2100 was confirmed. Reference Examples 13 to 20 Various phosphate ester compounds were obtained in the same manner as Reference Example 12, except that the materials listed in Table 2 below were used in place of the materials in Reference Example 12. Example 1 Copper phthalocyanine blue pigment (CI Pigment Blue 15-3) aqueous filter cake (pigment content 42
%) 238 copies were placed in a flasher. Separately,
The phosphate group of Dispersant 1 obtained in Reference Example 1 was neutralized with approximately the same amount of rosin amine to prepare a salt. 60 parts of this rosin amine salt was dissolved in 40 parts of petroleum-based ink solvent and added, kneaded and flushed according to a conventional method. The water content of the cake was released much more easily than conventional flushing aids, and the copper phthalocyanine blue pigment was transferred to the oil-based dispersant. Furthermore, water was completely removed to obtain a flushed color containing copper phthalocyanine blue pigment.
An offset lithography ink was prepared using the flat color containing the copper phthalocyanine blue pigment obtained above. Flatusid color of the copper phthalocyanine blue pigment obtained above (50% purity) 38.0 parts Mixed varnish for offset single plate ink 60.0 parts 5% cobalt dryer 0.2 parts 8% manganese dryer 1.0 parts Ink solvent 0.8 parts Total 100 parts Above The varnish for offset lithographic ink has the following composition. Rosin-modified phenolic resin 35 parts Drying oil 25 parts Drying oil-modified isophthalic acid alkyd 10 parts Ink solvent 29.5 parts Aluminum chelate 0.5 parts Total 100 parts The copper phthalocyanine blue pigment ink obtained above was used as an indigo ink and printed using an offset printing machine. It was printed on paper and a clear blue print was obtained. Also, instead of the aqueous filter cake of copper phthalocyanine blue pigment, disazo yellow pigment (C.
I. Pigment Yellow 12) aqueous filter cake (pigment content 27%) and Brilliant Carmine 6B pigment (CI Pigment Red 57-1) aqueous filter cake (pigment content 25%) in the same manner as above. A flush color was prepared, and then yellow and red offset lithographic inks were prepared respectively. Similarly, a flush color was obtained from an aqueous filter cake of Laked C pigment (CI Pigment Red 53-1), and a gold red ink for offset lithography was obtained. Also, a flush color was obtained from an aqueous filter cake of copper phthalocyanine blue pigment (CI Pigment Green 7), and a grass ink for offset lithography was obtained. In each case, water was easily separated in flushing and showed excellent transition to an oil phase, and clear and excellent printed matter was obtained in offset lithographic printing. Furthermore, Dispersant 2 to Dispersant 20 were used in place of Dispersant 1 used above, and the same excellent effects as above were obtained. In addition, in place of the rosin amine in which the phosphate group of the dispersant is neutralized in the above, a salt of a dispersant obtained by neutralizing with coconut amine, beef tallow propylene diamine, or calcium, strontium, or aluminum hydroxide is used. , the same excellent effects as above were obtained. Example 2 Carbon black pigment 20 parts Beef tallow propylene diamine salt of dispersant 1 obtained in Reference Example 1 6 parts Mixed varnish for offset planographic ink 69 parts A total of 95 parts of carbon black pigment was kneaded using three rolls. and dispersed. The carbon black pigment was very well dispersed in the varnish. Varnish dispersion of carbon black pigment obtained above 95 parts 5% cobalt dryer 0.2 parts 8% manganese dryer 1.0 parts Isoxol vent 3.8 parts Total 100 parts were thoroughly mixed and kneaded to obtain carbon black ink. . This was used to print with an offset printing machine to obtain a black printed matter with a high degree of blackness. Further, in place of Dispersant 1 used above, Dispersants 2 to 20 were used, and the same excellent effects as above were obtained. In addition, in place of the beef tallow propylene diamine that has neutralized the phosphate group of the dispersant in the above, a dispersant obtained by neutralizing it with rosin amine, coconut amine, coconut propylene diamine, or a hydroxide of calcium, strontium, or aluminum. The same excellent effect as above was obtained using the salt. In addition, the black ink obtained above was added to the yellow ink, red ink, and blue ink obtained in the examples to obtain four colors of process yellow ink, process red ink, process blue ink, and process black ink for offset lithography. Process printing was performed and clear and beautiful multicolor printed matter was obtained. Example 3 Flush color of copper phthalocyanine blue pigment obtained in Example 1 (purity 50%) 10.8 parts Rutile titanium white 2.0 parts Quick-drying styrenated alkyd resin 72.6 parts Xylol 6.6 parts Mineral spirits 7.6 parts 6 % cobalt naphthenate 0.3 parts anti-skinning agent 0.1 part A total of 100 parts of the formulation was thoroughly and uniformly mixed and dispersed to obtain a blue quick-drying enamel that dries at room temperature for metal materials such as machines and vehicles. When applied, the paint was clear and beautiful. Next, in place of the copper phthalocyanine blue pigment of Example 1, disazo yellow (CI Pigment Yellow 14), a fast yellow pigment prepared by diazotizing 4-aminophthalimide and coupling it with acetoacetanilide, and watching red ( Flushing was carried out in the same manner as in Example 1 using the aqueous filter cakes of pigments CI Pigment Red 48) and Carmine FB (CI Pigment Red 3) to obtain flush colors of each pigment. These were used in place of the copper phthalocyanine pigment in the composition of the above paint, and paints of various colors were obtained, and clear and beautiful coated plates were obtained. Example 4 Dry and crushed pigment of copper phthalocyanine blue pigment (CI Pigment Blue 15-3) 10 parts Salt obtained by neutralizing the acid radical of Dispersant 1 obtained in Reference Example 1 with approximately equal equivalent amount of triethylamine 2 parts xylol 13 parts butanol A total of 30 parts ( 5 parts) were dispersed using a continuous horizontal media disperser to obtain a dispersion of copper phthalocyanine blue pigment in a xyol-butanol mixed solvent. Next, a paint was prepared using the following recipe. Copper phthalocyanine blue obtained above and dispersant 1
3 parts rutile titanium white 14 parts thermoplastic acrylic resin 70 parts toluene 6.8 parts xylol 3.2 parts butanol 2.2 parts cellosolve 0.8 parts total 100 parts This was used as an acrylic lacquer enamel for automobiles. A clear and beautiful coating was obtained. Further, by using Dispersant 2 to Dispersant 20 in place of Dispersant 1 used above, excellent coating materials were obtained in the same manner as above. In addition, instead of the triethylamine that neutralized the phosphate group of the dispersant in the above, rosin amine, coconut amine, beef tallow propylene diamine, coconut propylene diamine, or a hydroxide of calcium, strontium, or aluminum was used to neutralize the dispersant. Similar excellent effects as above were obtained using the dispersant salt.
【表】【table】
【表】
平均分子量
[Table] Average molecular weight
【表】【table】
【表】【table】
【表】
主成分の平均分子量。
これらは参考例１のリン酸ジエステルと同様
に、酸の形、有機アミン塩及び金属塩の形で顔料
分散剤及びフラツシング剤等として有用であつ
た。[Table] Average molecular weight of main components.
Like the phosphoric acid diester of Reference Example 1, these were useful as pigment dispersants, flushing agents, etc. in the form of acids, organic amine salts, and metal salts.
Claims (1)
て、該分散剤が、下記一般式で表されるリン酸エ
ステル化合物又はそれらのアンモニウム塩、第１
級〜第３級有機アミン塩、有機第４級アンモニウ
ム塩又は１〜３価の金属塩であることを特徴とす
る顔料組成物。 ［但しR1は、炭素数４〜30の炭化水素基である。
R2は、R3OOC−R1［―Ｏ・OC−R1〕―o、水素原子
又は炭素数１〜30の炭化水素基である。R3は水
素原子又は炭素数１〜30の炭化水素基である。ｎ
は１以上で分子量が10000以下になる値である。］[Scope of Claims] 1. A pigment composition containing a pigment and a dispersant, wherein the dispersant is a phosphoric acid ester compound represented by the following general formula or an ammonium salt thereof,
A pigment composition characterized in that it is a grade to tertiary organic amine salt, an organic quaternary ammonium salt, or a monovalent to trivalent metal salt. [However, R 1 is a hydrocarbon group having 4 to 30 carbon atoms.
R2 is R3OOC - R1 [-O.OC- R1 ] -o , a hydrogen atom, or a hydrocarbon group having 1 to 30 carbon atoms. R 3 is a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms. n
is a value of 1 or more and the molecular weight is 10,000 or less. ]
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60033492A JPS61194091A (en) | 1985-02-21 | 1985-02-21 | Phosphoric acid ester |
| JP60106982A JPS61266472A (en) | 1985-02-21 | 1985-05-21 | Pigment composition and process for preparing same |
| JP60210293A JPS6270455A (en) | 1985-09-25 | 1985-09-25 | Pigment composition and production thereof |
| US06/824,576 US4698099A (en) | 1985-02-21 | 1986-01-23 | Pigment composition |
| CA000501035A CA1279140C (en) | 1985-02-21 | 1986-02-04 | Pigment composition |
| DE86101686T DE3688401T2 (en) | 1985-02-21 | 1986-02-10 | Pigment composition. |
| EP86101686A EP0192160B1 (en) | 1985-02-21 | 1986-02-10 | Pigment composition |
| AT86101686T ATE89301T1 (en) | 1985-02-21 | 1986-02-10 | PIGMENT COMPOSITION. |
| AU65898/86A AU583963B2 (en) | 1985-02-21 | 1986-12-02 | Phosphoric ester compound |
| AU65896/86A AU587660B2 (en) | 1985-02-21 | 1986-12-02 | Pigment composition |
| AU65899/86A AU591735B2 (en) | 1985-02-21 | 1986-12-02 | Pigment composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60210293A JPS6270455A (en) | 1985-09-25 | 1985-09-25 | Pigment composition and production thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6270455A JPS6270455A (en) | 1987-03-31 |
| JPH0511150B2 true JPH0511150B2 (en) | 1993-02-12 |
Family
ID=16586997
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60210293A Granted JPS6270455A (en) | 1985-02-21 | 1985-09-25 | Pigment composition and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6270455A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6180302B2 (en) * | 2013-11-29 | 2017-08-16 | 富士フイルム株式会社 | Colored photosensitive resin composition, cured film, pattern, color filter, method for producing color filter, solid-state imaging device, and image display device |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52969A (en) * | 1975-06-24 | 1977-01-06 | Shin Meiwa Ind Co Ltd | Alllround solid mould |
| JPS5813209A (en) * | 1981-07-02 | 1983-01-25 | ダンフオス・エ−・エス | Hydraulic controller |
| JPS5910750A (en) * | 1982-07-07 | 1984-01-20 | Mazda Motor Corp | Engine throttle valve controller |
| JPS60161730A (en) * | 1984-01-31 | 1985-08-23 | Sanyo Chem Ind Ltd | Dispersant and composition of antimony oxide |
| JPS60210292A (en) * | 1984-09-25 | 1985-10-22 | 松下電器産業株式会社 | Drainage of one-tub type dehydration washer |
-
1985
- 1985-09-25 JP JP60210293A patent/JPS6270455A/en active Granted
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52969A (en) * | 1975-06-24 | 1977-01-06 | Shin Meiwa Ind Co Ltd | Alllround solid mould |
| JPS5813209A (en) * | 1981-07-02 | 1983-01-25 | ダンフオス・エ−・エス | Hydraulic controller |
| JPS5910750A (en) * | 1982-07-07 | 1984-01-20 | Mazda Motor Corp | Engine throttle valve controller |
| JPS60161730A (en) * | 1984-01-31 | 1985-08-23 | Sanyo Chem Ind Ltd | Dispersant and composition of antimony oxide |
| JPS60210292A (en) * | 1984-09-25 | 1985-10-22 | 松下電器産業株式会社 | Drainage of one-tub type dehydration washer |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6270455A (en) | 1987-03-31 |
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