CA1124916A - Fine spherical polymer particles containing inorganic pigment and/or coloring agent and process for the preparation thereof - Google Patents
Fine spherical polymer particles containing inorganic pigment and/or coloring agent and process for the preparation thereofInfo
- Publication number
- CA1124916A CA1124916A CA331,226A CA331226A CA1124916A CA 1124916 A CA1124916 A CA 1124916A CA 331226 A CA331226 A CA 331226A CA 1124916 A CA1124916 A CA 1124916A
- Authority
- CA
- Canada
- Prior art keywords
- polymer particles
- particle size
- particles
- polymerizable monomers
- dispersion stabilizer
- 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
Links
- 239000002245 particle Substances 0.000 title claims abstract description 277
- 229920000642 polymer Polymers 0.000 title claims abstract description 78
- 238000000034 method Methods 0.000 title claims abstract description 76
- 239000001023 inorganic pigment Substances 0.000 title claims abstract description 19
- 239000003086 colorant Substances 0.000 title claims abstract description 18
- 230000008569 process Effects 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 239000000178 monomer Substances 0.000 claims abstract description 73
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 62
- 239000006185 dispersion Substances 0.000 claims abstract description 40
- 239000003381 stabilizer Substances 0.000 claims abstract description 37
- 238000009826 distribution Methods 0.000 claims abstract description 27
- 238000010557 suspension polymerization reaction Methods 0.000 claims abstract description 19
- 229920005989 resin Polymers 0.000 claims description 76
- 239000011347 resin Substances 0.000 claims description 76
- 239000000203 mixture Substances 0.000 claims description 71
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 60
- 239000007788 liquid Substances 0.000 claims description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 31
- 239000000126 substance Substances 0.000 claims description 24
- 239000006229 carbon black Substances 0.000 claims description 17
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical group O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 16
- 125000000129 anionic group Chemical group 0.000 claims description 11
- 125000002091 cationic group Chemical group 0.000 claims description 11
- 238000010008 shearing Methods 0.000 claims description 11
- 150000001450 anions Chemical class 0.000 claims description 8
- 150000001768 cations Chemical class 0.000 claims description 8
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000005011 phenolic resin Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000002270 dispersing agent Substances 0.000 claims description 5
- 239000003822 epoxy resin Substances 0.000 claims description 5
- 229920000647 polyepoxide Polymers 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000000440 bentonite Substances 0.000 claims description 4
- 229910000278 bentonite Inorganic materials 0.000 claims description 4
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 4
- 239000008119 colloidal silica Substances 0.000 claims description 4
- 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 claims description 4
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 229920006122 polyamide resin Polymers 0.000 claims description 3
- GZBSIABKXVPBFY-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO GZBSIABKXVPBFY-UHFFFAOYSA-N 0.000 claims description 2
- 229910001021 Ferroalloy Inorganic materials 0.000 claims description 2
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 claims description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 2
- HSZUHSXXAOWGQY-UHFFFAOYSA-N [2-methyl-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(C)(COC(=O)C=C)COC(=O)C=C HSZUHSXXAOWGQY-UHFFFAOYSA-N 0.000 claims description 2
- 239000000980 acid dye Substances 0.000 claims description 2
- 239000000981 basic dye Substances 0.000 claims description 2
- 229920002857 polybutadiene Polymers 0.000 claims description 2
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 claims 1
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 claims 1
- 239000005062 Polybutadiene Substances 0.000 claims 1
- 239000012860 organic pigment Substances 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- 239000000992 solvent dye Substances 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 description 107
- 238000003756 stirring Methods 0.000 description 70
- 239000012798 spherical particle Substances 0.000 description 68
- 239000012153 distilled water Substances 0.000 description 33
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 26
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 20
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 17
- 239000011521 glass Substances 0.000 description 17
- 235000019241 carbon black Nutrition 0.000 description 16
- SZVJSHCCFOBDDC-UHFFFAOYSA-N ferrosoferric oxide Chemical compound O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 16
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 14
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 14
- 239000000843 powder Substances 0.000 description 14
- 239000000725 suspension Substances 0.000 description 13
- 238000004581 coalescence Methods 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 10
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 9
- 229910052742 iron Inorganic materials 0.000 description 9
- -1 a-chlorostyr~ne Chemical compound 0.000 description 8
- 229940056319 ferrosoferric oxide Drugs 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000375 suspending agent Substances 0.000 description 8
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 7
- AJCDFVKYMIUXCR-UHFFFAOYSA-N oxobarium;oxo(oxoferriooxy)iron Chemical compound [Ba]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O AJCDFVKYMIUXCR-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 6
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- XOYONZYDWNTDAL-UHFFFAOYSA-N n-butoxyprop-2-enamide Chemical compound CCCCONC(=O)C=C XOYONZYDWNTDAL-UHFFFAOYSA-N 0.000 description 6
- 229910052725 zinc Inorganic materials 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 229910002012 Aerosil® Inorganic materials 0.000 description 5
- 239000004342 Benzoyl peroxide Substances 0.000 description 5
- IRERQBUNZFJFGC-UHFFFAOYSA-L azure blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[S-]S[S-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] IRERQBUNZFJFGC-UHFFFAOYSA-L 0.000 description 5
- 235000019400 benzoyl peroxide Nutrition 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 5
- 239000011800 void material Substances 0.000 description 5
- 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 4
- 229910000531 Co alloy Inorganic materials 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- 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 4
- 238000007796 conventional method Methods 0.000 description 4
- 230000005611 electricity Effects 0.000 description 4
- 238000001962 electrophoresis Methods 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 4
- 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 4
- NIBPGNKODUOZIW-UHFFFAOYSA-M (2-hydroxy-3-prop-2-enoyloxypropyl)-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)COC(=O)C=C NIBPGNKODUOZIW-UHFFFAOYSA-M 0.000 description 3
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 3
- 229910002019 Aerosil® 380 Inorganic materials 0.000 description 3
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 3
- 239000010419 fine particle Substances 0.000 description 3
- 238000001879 gelation Methods 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- QHVBLSNVXDSMEB-UHFFFAOYSA-N 2-(diethylamino)ethyl prop-2-enoate Chemical compound CCN(CC)CCOC(=O)C=C QHVBLSNVXDSMEB-UHFFFAOYSA-N 0.000 description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-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
- 241000721047 Danaus plexippus Species 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- 229910001030 Iron–nickel alloy Inorganic materials 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- KGWWEXORQXHJJQ-UHFFFAOYSA-N [Fe].[Co].[Ni] Chemical compound [Fe].[Co].[Ni] KGWWEXORQXHJJQ-UHFFFAOYSA-N 0.000 description 2
- 229940019789 acid black 52 Drugs 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- XRPLBRIHZGVJIC-UHFFFAOYSA-L chembl3182776 Chemical compound [Na+].[Na+].NC1=CC(N)=CC=C1N=NC1=CC=C(C=2C=CC(=CC=2)N=NC=2C(=CC3=CC(=C(N=NC=4C=CC=CC=4)C(O)=C3C=2N)S([O-])(=O)=O)S([O-])(=O)=O)C=C1 XRPLBRIHZGVJIC-UHFFFAOYSA-L 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000011362 coarse particle Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- AOMZHDJXSYHPKS-UHFFFAOYSA-L disodium 4-amino-5-hydroxy-3-[(4-nitrophenyl)diazenyl]-6-phenyldiazenylnaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC2=CC(S([O-])(=O)=O)=C(N=NC=3C=CC=CC=3)C(O)=C2C(N)=C1N=NC1=CC=C([N+]([O-])=O)C=C1 AOMZHDJXSYHPKS-UHFFFAOYSA-L 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 2
- 239000011164 primary particle Substances 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 238000010558 suspension polymerization method Methods 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 235000014692 zinc oxide Nutrition 0.000 description 2
- JMYZLRSSLFFUQN-UHFFFAOYSA-N (2-chlorobenzoyl) 2-chlorobenzenecarboperoxoate Chemical compound ClC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1Cl JMYZLRSSLFFUQN-UHFFFAOYSA-N 0.000 description 1
- WOTCBNVQQFUGLX-UHFFFAOYSA-N (2-methoxybenzoyl) 2-methoxybenzenecarboperoxoate Chemical compound COC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1OC WOTCBNVQQFUGLX-UHFFFAOYSA-N 0.000 description 1
- DZSVIVLGBJKQAP-UHFFFAOYSA-N 1-(2-methyl-5-propan-2-ylcyclohex-2-en-1-yl)propan-1-one Chemical compound CCC(=O)C1CC(C(C)C)CC=C1C DZSVIVLGBJKQAP-UHFFFAOYSA-N 0.000 description 1
- KPAPHODVWOVUJL-UHFFFAOYSA-N 1-benzofuran;1h-indene Chemical compound C1=CC=C2CC=CC2=C1.C1=CC=C2OC=CC2=C1 KPAPHODVWOVUJL-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- AHEAPQJDMSHYKL-UHFFFAOYSA-N 1H-indene 5-phenylpenta-2,4-dienenitrile Chemical compound C1=CC=C2CC=CC2=C1.N#CC=CC=CC1=CC=CC=C1 AHEAPQJDMSHYKL-UHFFFAOYSA-N 0.000 description 1
- TZJQCUDHKUWEFU-UHFFFAOYSA-N 2,2-dimethylpentanenitrile Chemical compound CCCC(C)(C)C#N TZJQCUDHKUWEFU-UHFFFAOYSA-N 0.000 description 1
- WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0097—Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
- C09B67/0063—Preparation of organic pigments of organic pigments with only macromolecular substances
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S524/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S524/904—Powder coating compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polymerisation Methods In General (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Developing Agents For Electrophotography (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP81949/78 | 1978-07-07 | ||
| JP81950/78 | 1978-07-07 | ||
| JP8194978A JPS559632A (en) | 1978-07-07 | 1978-07-07 | Fine spherical polymer particle containing inorganic pigment and its production |
| JP8195078A JPS559633A (en) | 1978-07-07 | 1978-07-07 | Blackened fine spherical polymer particle and its production |
| JP13733878A JPS5580404A (en) | 1978-11-09 | 1978-11-09 | Black colored fine spherical polymer particle containing resin and preparation thereof |
| JP137337/78 | 1978-11-09 | ||
| JP13733778A JPS5580403A (en) | 1978-11-09 | 1978-11-09 | Fine spherical polymer particle containing inorganic pigment and resin and preparation thereof |
| JP137338/78 | 1978-11-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1124916A true CA1124916A (en) | 1982-06-01 |
Family
ID=27466640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA331,226A Expired CA1124916A (en) | 1978-07-07 | 1979-07-05 | Fine spherical polymer particles containing inorganic pigment and/or coloring agent and process for the preparation thereof |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4314932A (cg-RX-API-DMAC7.html) |
| CA (1) | CA1124916A (cg-RX-API-DMAC7.html) |
| DE (1) | DE2927249A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2430427A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB2029425B (cg-RX-API-DMAC7.html) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5659802A (en) * | 1979-10-23 | 1981-05-23 | Shinroihi Kk | Microspherical polymer particle and production thereof |
| JPS56110946A (en) * | 1980-02-06 | 1981-09-02 | Konishiroku Photo Ind Co Ltd | Toner for electrostatic charge image development and its production |
| JPS56154739A (en) * | 1980-05-02 | 1981-11-30 | Konishiroku Photo Ind Co Ltd | Toner for developing electrostatic charge image and its manufacture |
| JPS57149314A (en) * | 1981-03-12 | 1982-09-14 | Mitsubishi Rayon Co Ltd | Production of novel polymer composition |
| GB2090602B (en) * | 1981-01-06 | 1984-08-15 | Mitsubishi Rayon Co | Polymer composition |
| DE3689160T2 (de) * | 1985-08-29 | 1994-05-05 | Mitsubishi Rayon Co | Verfahren zur Herstellung einer Polymerzusammensetzung. |
| JPH01150154A (ja) * | 1987-12-08 | 1989-06-13 | Canon Inc | 静電荷像現像用トナーの製造方法 |
| US4835084A (en) * | 1988-03-21 | 1989-05-30 | Eastman Kodak Company | Electrostatographic toner and method of producing the same |
| US4833060A (en) * | 1988-03-21 | 1989-05-23 | Eastman Kodak Company | Polymeric powders having a predetermined and controlled size and size distribution |
| DE3824333A1 (de) * | 1988-07-18 | 1990-01-25 | Fraunhofer Ges Forschung | Verfahren zur fixierung einer anorganischen spezies in einer organischen matrix |
| US4912009A (en) * | 1988-12-30 | 1990-03-27 | Eastman Kodak Company | Toner composition and method of making |
| US5126394A (en) * | 1989-10-18 | 1992-06-30 | Dow Corning Corporation | Radiation curable abrasion resistant coatings from colloidal silica and acrylate monomer |
| US5188900A (en) * | 1989-10-18 | 1993-02-23 | Dow Corning Corporation | Substrates having an abrasion-resistant coating formed thereon |
| US5738694A (en) * | 1994-01-21 | 1998-04-14 | Covol Technologies, Inc. | Process for recovering iron from iron-containing material |
| US5589118A (en) * | 1994-01-21 | 1996-12-31 | Covol Technologies, Inc. | Process for recovering iron from iron-containing material |
| AUPM695294A0 (en) * | 1994-07-20 | 1994-08-11 | Borody, Thomas Julius | Improved combination therapy dose unit |
| AUPM807094A0 (en) * | 1994-09-09 | 1994-10-06 | Commonwealth Scientific And Industrial Research Organisation | Polymer beads and method for preparation thereof |
| EP0725317A1 (en) | 1995-01-30 | 1996-08-07 | Agfa-Gevaert N.V. | Polymer suspension method for producing toner particles |
| RU2147617C1 (ru) * | 1995-06-06 | 2000-04-20 | Ковол Текнолоджиз, Инк. | Способ извлечения железа из железосодержащих материалов |
| NZ303005A (en) * | 1995-06-06 | 1998-11-25 | Covol Tech Inc | Process for recovering iron from iron-rich material |
| US5728786A (en) * | 1996-07-15 | 1998-03-17 | Minnesota Mining And Manufacturing Company | Styrl-modified acrylate polymer pressure sensitive adhesive beads |
| EP1091801A4 (en) * | 1998-05-30 | 2006-05-10 | Univ Kansas State | POROUS PELLET ADSORBENTS MADE FROM SINGLE CRYSTALS |
| US6093236A (en) * | 1998-05-30 | 2000-07-25 | Kansas State University Research Foundation | Porous pellet adsorbents fabricated from nanocrystals |
| JP3877970B2 (ja) * | 2001-04-06 | 2007-02-07 | 株式会社トクヤマ | 変性乾式シリカ分散液 |
| KR100437224B1 (ko) * | 2001-08-29 | 2004-06-23 | 주식회사 태평양 | 자외선 산란용 무기/고분자 복합입자 및 그의 제조방법 |
| US8192909B2 (en) | 2005-12-21 | 2012-06-05 | Eastman Kodak Company | Chemically prepared porous toner |
| TWI350071B (en) * | 2006-09-11 | 2011-10-01 | Univ Nat Taiwan Science Tech | Detection system for identifying faults in a passive optical network |
| US20090149591A1 (en) * | 2007-12-07 | 2009-06-11 | Yong Yang | Paint Compositions With Low- or Zero-VOC Coalescence Aids and Nano-Particle Pigments |
| US8299140B2 (en) | 2007-12-21 | 2012-10-30 | Eastman Kodak Company | Discrete ink particle with solid phase and liquid phase |
| US8299141B2 (en) | 2007-12-21 | 2012-10-30 | Eastman Kodak Company | Mixed phase method of manufacturing ink |
| US8614039B2 (en) | 2010-04-26 | 2013-12-24 | Eastman Kodak Company | Toner containing metallic flakes and method of forming metallic image |
| US8722304B2 (en) | 2010-07-30 | 2014-05-13 | Eastman Kodak Company | Method for forming surface decorated particles |
| US8728692B2 (en) | 2010-07-30 | 2014-05-20 | Eastman Kodak Company | Surface decorated particles |
| US8507089B2 (en) | 2011-01-04 | 2013-08-13 | Eastman Kodak Company | Articles with porous particles for security purposes |
| US8507088B2 (en) | 2011-01-04 | 2013-08-13 | Eastman Kodak Company | Porous particles with multiple markers |
| WO2013016080A2 (en) | 2011-07-28 | 2013-01-31 | Eastman Kodak Company | Crosslinked organic porous particles |
| US8603725B2 (en) | 2011-07-28 | 2013-12-10 | Eastman Kodak Company | Laser-engraveable compositions and flexographic printing precursors |
| US8613999B2 (en) | 2011-07-28 | 2013-12-24 | Eastman Kodak Company | Laser-engraveable compositions and flexographic printing precursors comprising organic porous particles |
| US20130071143A1 (en) | 2011-09-19 | 2013-03-21 | Thomas Nelson Blanton | Antibacterial and antifungal protection for toner image |
| US9029431B2 (en) | 2012-11-28 | 2015-05-12 | Eastman Kodak Company | Porous particles and methods of making them |
| US9176405B2 (en) | 2013-10-18 | 2015-11-03 | Eastman Kodak Company | Polymeric composite materials, manufacture, and uses |
| CN116515191B (zh) * | 2023-06-01 | 2025-03-04 | 陕西延长泾渭新材料科技产业园有限公司 | 一种炭黑功能母粒及其制备方法与应用 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3117943A (en) * | 1957-12-05 | 1964-01-14 | Crylor | Pigmented vinyl polymers prepared by adsorbing vinyl monomer on carbon black and then polymerizing said monomer |
| US3183208A (en) * | 1961-08-22 | 1965-05-11 | Koppers Co Inc | Incorporating finely divided particles during suspension polymerization |
| GB1156653A (en) * | 1965-06-10 | 1969-07-02 | Ici Ltd | Coated Particles |
| JPS5114895B1 (cg-RX-API-DMAC7.html) * | 1968-03-06 | 1976-05-13 | ||
| DE2153043A1 (de) * | 1970-10-24 | 1972-04-27 | Pilot Pen Co Ltd | Aufzeichnungsmaterial |
| US3714102A (en) * | 1970-12-02 | 1973-01-30 | Gulf Oil Canada Ltd | Polymer encapsulation of finely divided solids |
| DE2162264C2 (de) * | 1970-12-16 | 1983-07-14 | Sinloihi Co. Ltd., Osaka | Verfahren zur Herstellung fluoreszierender gefärbter Kunstharzpartikel |
| CA995837A (en) * | 1970-12-22 | 1976-08-24 | Dai Nippon Toryo Co. | Dispersion of finely divided pigment particles and process for preparation of the same |
| JPS5146552B2 (cg-RX-API-DMAC7.html) * | 1972-12-04 | 1976-12-09 | ||
| JPS5247355B2 (cg-RX-API-DMAC7.html) * | 1974-10-15 | 1977-12-01 | ||
| DE2559375A1 (de) * | 1975-12-31 | 1977-07-07 | Bayer Ag | Verfahren zur herstellung von pigmenten verbesserter dispergierbarkeit und ihre verwendung |
| US4071670A (en) * | 1976-08-02 | 1978-01-31 | Xerox Corporation | Method of sizing monomer droplets for suspension polymerization to form small particles |
-
1979
- 1979-07-05 CA CA331,226A patent/CA1124916A/en not_active Expired
- 1979-07-05 FR FR7917509A patent/FR2430427A1/fr active Granted
- 1979-07-05 DE DE19792927249 patent/DE2927249A1/de not_active Ceased
- 1979-07-06 GB GB7923697A patent/GB2029425B/en not_active Expired
-
1980
- 1980-08-18 US US06/178,930 patent/US4314932A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2430427A1 (fr) | 1980-02-01 |
| US4314932A (en) | 1982-02-09 |
| GB2029425B (en) | 1982-08-04 |
| FR2430427B1 (cg-RX-API-DMAC7.html) | 1985-05-24 |
| DE2927249A1 (de) | 1980-01-17 |
| GB2029425A (en) | 1980-03-19 |
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry |