CA2347093C - Polymer coated carbon products and other pigments and methods of making same by aqueous media polymerizations or solvent coating methods - Google Patents
Polymer coated carbon products and other pigments and methods of making same by aqueous media polymerizations or solvent coating methods Download PDFInfo
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- CA2347093C CA2347093C CA002347093A CA2347093A CA2347093C CA 2347093 C CA2347093 C CA 2347093C CA 002347093 A CA002347093 A CA 002347093A CA 2347093 A CA2347093 A CA 2347093A CA 2347093 C CA2347093 C CA 2347093C
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- modified carbon
- carbon product
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- 229920000642 polymer Polymers 0.000 title claims abstract description 269
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims abstract description 120
- 238000000034 method Methods 0.000 title claims abstract description 105
- 229910052799 carbon Inorganic materials 0.000 title claims abstract description 89
- 238000000576 coating method Methods 0.000 title claims abstract description 76
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 58
- 239000002904 solvent Substances 0.000 title claims abstract description 51
- 239000000049 pigment Substances 0.000 title description 17
- 239000012736 aqueous medium Substances 0.000 title description 11
- 150000001721 carbon Chemical class 0.000 claims abstract description 276
- 125000000962 organic group Chemical group 0.000 claims abstract description 107
- 239000003960 organic solvent Substances 0.000 claims abstract description 8
- 239000006229 carbon black Substances 0.000 claims description 147
- 239000000178 monomer Substances 0.000 claims description 86
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 79
- 239000000203 mixture Substances 0.000 claims description 76
- 239000011248 coating agent Substances 0.000 claims description 64
- 239000003999 initiator Substances 0.000 claims description 57
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 53
- -1 sulfophenyl group Chemical group 0.000 claims description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 40
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 23
- 239000006185 dispersion Substances 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 239000004793 Polystyrene Substances 0.000 claims description 19
- 238000001704 evaporation Methods 0.000 claims description 16
- 238000010526 radical polymerization reaction Methods 0.000 claims description 15
- 239000011159 matrix material Substances 0.000 claims description 14
- 239000004094 surface-active agent Substances 0.000 claims description 11
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 10
- 229920001577 copolymer Polymers 0.000 claims description 10
- 230000008020 evaporation Effects 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 238000001914 filtration Methods 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 229920000098 polyolefin Polymers 0.000 claims description 8
- 239000004594 Masterbatch (MB) Substances 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 239000004417 polycarbonate Substances 0.000 claims description 7
- 229920002223 polystyrene Polymers 0.000 claims description 7
- 239000010410 layer Substances 0.000 claims description 6
- 229920000049 Carbon (fiber) Polymers 0.000 claims description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000004917 carbon fiber Substances 0.000 claims description 5
- 229910021397 glassy carbon Inorganic materials 0.000 claims description 5
- 229910002804 graphite Inorganic materials 0.000 claims description 5
- 239000010439 graphite Substances 0.000 claims description 5
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 5
- 229920000515 polycarbonate Polymers 0.000 claims description 5
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 239000010703 silicon Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 4
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- 229910052736 halogen Inorganic materials 0.000 claims description 4
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- 238000011065 in-situ storage Methods 0.000 claims description 4
- 229920001778 nylon Polymers 0.000 claims description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 4
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- 239000004800 polyvinyl chloride Substances 0.000 claims description 4
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 238000001694 spray drying Methods 0.000 claims description 4
- 125000000626 sulfinic acid group Chemical group 0.000 claims description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
- 238000012546 transfer Methods 0.000 claims description 4
- 229920001567 vinyl ester resin Polymers 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 3
- 229920000106 Liquid crystal polymer Polymers 0.000 claims description 3
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 claims description 3
- 229920000877 Melamine resin Polymers 0.000 claims description 3
- 229920002292 Nylon 6 Polymers 0.000 claims description 3
- 239000004962 Polyamide-imide Substances 0.000 claims description 3
- 239000004698 Polyethylene Substances 0.000 claims description 3
- 229920002367 Polyisobutene Polymers 0.000 claims description 3
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 229920001807 Urea-formaldehyde Polymers 0.000 claims description 3
- 229920000180 alkyd Polymers 0.000 claims description 3
- 150000001555 benzenes Chemical class 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 229920002313 fluoropolymer Polymers 0.000 claims description 3
- 239000004811 fluoropolymer Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000000468 ketone group Chemical group 0.000 claims description 3
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- 229920000126 latex Polymers 0.000 claims description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 3
- 150000002978 peroxides Chemical group 0.000 claims description 3
- 229920001568 phenolic resin Polymers 0.000 claims description 3
- 229920002312 polyamide-imide Polymers 0.000 claims description 3
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- 238000001556 precipitation Methods 0.000 claims description 3
- 229920005573 silicon-containing polymer Polymers 0.000 claims description 3
- 229910052709 silver Inorganic materials 0.000 claims description 3
- 239000004332 silver Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 229920002725 thermoplastic elastomer Polymers 0.000 claims description 3
- 229920006305 unsaturated polyester Polymers 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 238000005119 centrifugation Methods 0.000 claims description 2
- 238000007156 chain growth polymerization reaction Methods 0.000 claims description 2
- 238000005345 coagulation Methods 0.000 claims description 2
- 230000015271 coagulation Effects 0.000 claims description 2
- 238000007155 step growth polymerization reaction Methods 0.000 claims description 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 238000010557 suspension polymerization reaction Methods 0.000 claims description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 1
- 229920002396 Polyurea Polymers 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 230000008021 deposition Effects 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 238000012643 polycondensation polymerization Methods 0.000 claims 1
- 239000002356 single layer Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 8
- 239000000047 product Substances 0.000 description 238
- 235000019241 carbon black Nutrition 0.000 description 135
- 238000006243 chemical reaction Methods 0.000 description 65
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 44
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 32
- 229920001897 terpolymer Polymers 0.000 description 30
- 239000000243 solution Substances 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000001030 gas--liquid chromatography Methods 0.000 description 27
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 27
- 239000000839 emulsion Substances 0.000 description 26
- 229920000638 styrene acrylonitrile Polymers 0.000 description 25
- 150000001875 compounds Chemical class 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000463 material Substances 0.000 description 20
- 239000002609 medium Substances 0.000 description 19
- 230000008569 process Effects 0.000 description 19
- 239000012954 diazonium Substances 0.000 description 18
- 150000001989 diazonium salts Chemical class 0.000 description 18
- 238000009472 formulation Methods 0.000 description 18
- 239000002245 particle Substances 0.000 description 17
- 238000002474 experimental method Methods 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000002156 mixing Methods 0.000 description 15
- 230000002378 acidificating effect Effects 0.000 description 14
- 238000000113 differential scanning calorimetry Methods 0.000 description 12
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- 230000004907 flux Effects 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 235000019395 ammonium persulphate Nutrition 0.000 description 9
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- 125000000524 functional group Chemical group 0.000 description 9
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- 230000000694 effects Effects 0.000 description 8
- 239000000945 filler Substances 0.000 description 8
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 7
- 150000001450 anions Chemical class 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 241000894007 species Species 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
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- 208000016261 weight loss Diseases 0.000 description 6
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- 150000001412 amines Chemical class 0.000 description 5
- 239000000010 aprotic solvent Substances 0.000 description 5
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- 238000013329 compounding Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
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- 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 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
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- 125000001072 heteroaryl group Chemical group 0.000 description 4
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
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- 238000004566 IR spectroscopy Methods 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 3
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- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
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- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 3
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- 238000012360 testing method Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
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- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 2
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
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- 239000002585 base Substances 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
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- 125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 description 2
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- 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 2
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- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 2
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- 125000001424 substituent group Chemical group 0.000 description 2
- 235000001508 sulfur Nutrition 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- 238000002076 thermal analysis method Methods 0.000 description 2
- ILWJAOPQHOZXAN-UHFFFAOYSA-N 1,3-dithianyl Chemical group [CH]1SCCCS1 ILWJAOPQHOZXAN-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
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- QWOVZHUJHAFOJS-UHFFFAOYSA-N 4-amino-2-(4-sulfophenyl)benzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(C=2C=CC(=CC=2)S(O)(=O)=O)=C1 QWOVZHUJHAFOJS-UHFFFAOYSA-N 0.000 description 1
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- 238000005520 cutting process Methods 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
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- 229910021641 deionized water Inorganic materials 0.000 description 1
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- LFINSDKRYHNMRB-UHFFFAOYSA-N diazanium;oxido sulfate Chemical compound [NH4+].[NH4+].[O-]OS([O-])(=O)=O LFINSDKRYHNMRB-UHFFFAOYSA-N 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
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- 238000004821 distillation Methods 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
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- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
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- HDCXQTPVTAIPNZ-UHFFFAOYSA-N n-({[4-(aminosulfonyl)phenyl]amino}carbonyl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 HDCXQTPVTAIPNZ-UHFFFAOYSA-N 0.000 description 1
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- 239000003208 petroleum Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
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- 239000004014 plasticizer Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
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- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 235000019394 potassium persulphate Nutrition 0.000 description 1
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- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
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- 238000001228 spectrum Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000008054 sulfonate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/08—Ingredients agglomerated by treatment with a binding agent
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/44—Carbon
- C09C1/48—Carbon black
- C09C1/56—Treatment of carbon black ; Purification
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2002/00—Crystal-structural characteristics
- C01P2002/80—Crystal-structural characteristics defined by measured data other than those specified in group C01P2002/70
- C01P2002/88—Crystal-structural characteristics defined by measured data other than those specified in group C01P2002/70 by thermal analysis data, e.g. TGA, DTA, DSC
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/01—Particle morphology depicted by an image
- C01P2004/04—Particle morphology depicted by an image obtained by TEM, STEM, STM or AFM
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2991—Coated
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2991—Coated
- Y10T428/2998—Coated including synthetic resin or polymer
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/30—Self-sustaining carbon mass or layer with impregnant or other layer
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerisation Methods In General (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Graft Or Block Polymers (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10411798P | 1998-10-13 | 1998-10-13 | |
| US60/104,117 | 1998-10-13 | ||
| US09/317,706 | 1999-05-24 | ||
| US09/317,706 US6458458B1 (en) | 1998-10-13 | 1999-05-24 | Polymer coated carbon products and other pigments and methods of making same by aqueous media polymerizations or solvent coating methods |
| PCT/US1999/023429 WO2000022051A1 (en) | 1998-10-13 | 1999-10-08 | Polymer coated carbon products and other pigments and methods of making same by aqueous media polymerizations or solvent coating methods |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2347093A1 CA2347093A1 (en) | 2000-04-20 |
| CA2347093C true CA2347093C (en) | 2009-04-07 |
Family
ID=26801197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002347093A Expired - Fee Related CA2347093C (en) | 1998-10-13 | 1999-10-08 | Polymer coated carbon products and other pigments and methods of making same by aqueous media polymerizations or solvent coating methods |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6458458B1 (https=) |
| EP (1) | EP1124905B1 (https=) |
| JP (3) | JP2002527564A (https=) |
| KR (1) | KR100639724B1 (https=) |
| AT (1) | ATE331000T1 (https=) |
| AU (1) | AU6421299A (https=) |
| CA (1) | CA2347093C (https=) |
| DE (1) | DE69932071T2 (https=) |
| ES (1) | ES2262344T3 (https=) |
| WO (1) | WO2000022051A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108864774A (zh) * | 2018-07-20 | 2018-11-23 | 江南大学 | 一种棉织物染色用反应性自分散纳米炭黑的制备方法 |
Families Citing this family (84)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7247379B2 (en) | 1997-08-28 | 2007-07-24 | E Ink Corporation | Electrophoretic particles, and processes for the production thereof |
| US7002728B2 (en) | 1997-08-28 | 2006-02-21 | E Ink Corporation | Electrophoretic particles, and processes for the production thereof |
| ES2193059T3 (es) | 1999-03-05 | 2003-11-01 | Cabot Corp | Procedimiento para preparar pigmentos de color. |
| US6221143B1 (en) | 1999-03-12 | 2001-04-24 | Cabot Corporation | Cationic pigments and aqueous compositions containing same |
| EP1228150B1 (en) | 1999-10-28 | 2013-09-04 | Cabot Corporation | Ink jet inks, inks, and other compositions containing colored pigments |
| US6506245B1 (en) | 1999-10-28 | 2003-01-14 | Cabot Corporation | Ink jet inks, inks, and other compositions containing colored pigments |
| WO2001050117A1 (en) | 1999-12-30 | 2001-07-12 | Cabot Corporation | Sensors with improved properties |
| WO2001051566A1 (en) | 2000-01-07 | 2001-07-19 | Cabot Corporation | Polymers and other groups attached to pigments and subsequent reactions |
| US6534569B2 (en) | 2000-01-25 | 2003-03-18 | Cabot Corporation | Polymers containing modified pigments and methods of preparing the same |
| US6890373B2 (en) * | 2000-06-19 | 2005-05-10 | Bridgestone Corporation | Adsorbents, process for producing the same, and applications thereof |
| KR100776467B1 (ko) * | 2000-07-06 | 2007-11-16 | 캐보트 코포레이션 | 개질된 안료 생성물, 이의 분산액 및 이를 포함하는 조성물 |
| ATE495890T1 (de) | 2000-07-06 | 2011-02-15 | Cabot Corp | Druckplatten mit modifizierten pigmentprodukten |
| US6822781B1 (en) | 2000-10-24 | 2004-11-23 | Cabot Corporation | Gyricon displays containing modified particles |
| WO2002062906A1 (en) * | 2001-02-02 | 2002-08-15 | Cabot Corporation | Ink compositions comprising salts with polyvalent ions |
| US7230750B2 (en) | 2001-05-15 | 2007-06-12 | E Ink Corporation | Electrophoretic media and processes for the production thereof |
| DE10120821A1 (de) * | 2001-04-27 | 2002-10-31 | Sachtleben Chemie Gmbh | Mit Polyalken beschichtete, poröse Füllstoffe |
| US6712894B2 (en) | 2001-05-09 | 2004-03-30 | Cabot Corporation | Method of producing secure images using inks comprising modified pigment particles |
| JP4188091B2 (ja) * | 2001-05-15 | 2008-11-26 | イー インク コーポレイション | 電気泳動粒子 |
| US6641653B2 (en) | 2001-07-19 | 2003-11-04 | Cabot Corporation | Ink compositions comprising modified colored pigments and methods for preparing the same |
| KR100437224B1 (ko) * | 2001-08-29 | 2004-06-23 | 주식회사 태평양 | 자외선 산란용 무기/고분자 복합입자 및 그의 제조방법 |
| US20030050361A1 (en) * | 2001-09-05 | 2003-03-13 | Eastman Kodak Company | Ink jet ink composition |
| US6641656B2 (en) | 2001-10-17 | 2003-11-04 | Cabot Corporation | Dispersions comprising modified pigments |
| AU2003206405A1 (en) * | 2002-01-07 | 2003-07-24 | Cabot Corporation | Modified pigment products and black matrixes comprising same |
| US7001934B2 (en) * | 2002-01-24 | 2006-02-21 | Cabot Coroporation | Inkjet ink systems comprising a gelling agent |
| ATE444332T1 (de) * | 2002-03-27 | 2009-10-15 | Cabot Corp | Verfahren zur anbindung einer oder mehrerer organischer gruppen an ein teilchen |
| US7173078B2 (en) | 2002-04-12 | 2007-02-06 | Cabot Corporation | Process for preparing modified pigments |
| US6699319B2 (en) | 2002-05-06 | 2004-03-02 | Cabot Corporation | Process for preparing modified pigments |
| US6833026B2 (en) | 2002-05-10 | 2004-12-21 | Cabot Corporation | Modified pigments and process for preparing modified pigments |
| CA2411443A1 (en) * | 2002-11-07 | 2004-05-07 | Formmat Technologies Inc. | Method to produce graphite/polymer composites |
| US6936097B2 (en) * | 2003-04-16 | 2005-08-30 | Cabot Corporation | Modified organic colorants and dispersions, and methods for their preparation |
| US6942724B2 (en) * | 2003-04-16 | 2005-09-13 | Cabot Corporation | Modified organic colorants and dispersions, and methods for their preparation |
| KR20060041251A (ko) * | 2003-07-23 | 2006-05-11 | 도아고세이가부시키가이샤 | 수성 잉크 |
| US20050233203A1 (en) * | 2004-03-15 | 2005-10-20 | Hampden-Smith Mark J | Modified carbon products, their use in fluid/gas diffusion layers and similar devices and methods relating to the same |
| US20050256225A1 (en) * | 2004-05-11 | 2005-11-17 | Viola Michael S | Aqueous inkjet ink compositions comprising comb-branched copolymers |
| FR2871162B1 (fr) * | 2004-06-02 | 2007-06-29 | Univ Paris 7 Denis Diderot | Materiau de surface modifiee, son procede de preparation et ses utilisations |
| US7807321B2 (en) * | 2004-10-15 | 2010-10-05 | Cabot Corporation | High resistivity compositions |
| EP1833931B1 (en) * | 2004-12-17 | 2012-08-01 | Cabot Corporation | Inkjet inks comprising multi-layer pigments |
| US20060144410A1 (en) * | 2004-12-30 | 2006-07-06 | Philip Morris Usa Inc. | Surface-modified activated carbon in smoking articles |
| JP2008530306A (ja) * | 2005-02-11 | 2008-08-07 | カーネギー メロン ユニバーシティ | 改質された炭素粒子 |
| KR20080032210A (ko) * | 2005-07-22 | 2008-04-14 | 캐보트 코포레이션 | 안료 조성물의 제조 방법 |
| FR2892325B1 (fr) * | 2005-10-26 | 2008-01-18 | Alchimer Sa | Procede de modification de surfaces isolantes, semi-conductrices ou metalliques, et produits tels qu'obtenus |
| BRPI0618100B1 (pt) | 2005-10-31 | 2018-03-27 | Cabot Corporation | Corantes modificados e composições de tinta para jatos de tinta compreendendo corantes modificados |
| BRPI0709848B1 (pt) * | 2006-04-03 | 2018-03-27 | The University Of Sydney | Métodos para polimerizar monômero para formar polímero na superfície de material particulado sólido, para preparar uma dispersão de material particulado sólido encapsulado em polímero em um líquido hidrofílico, para preparar um polímero e para preparar uma tinta, carga, adesivo, toner, tinta líquida, base de revestimento, selante, produto de diagnóstico ou produto terapêutico, tinta, carga, adesivo, toner, tinta líquida, base de revestimento, selante, produto diagnóstico ou produto terapêutico, material particulado sólido encapsulado em polímero, composição, e, dispersão líquida |
| WO2008055244A2 (en) | 2006-10-31 | 2008-05-08 | Sensient Colors Inc. | Modified pigments and methods for making and using the same |
| US9725602B2 (en) * | 2006-12-19 | 2017-08-08 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Method for preparing an organic film at the surface of a solid support under non-electrochemical conditions, solid support thus obtained and preparation kit |
| FR2910006B1 (fr) * | 2006-12-19 | 2009-03-06 | Commissariat Energie Atomique | Procede de preparation d'un film organique a la surface d'un support solide dans des conditions non-electrochimiques, support solide ainsi obtenu et kit de preparation |
| FR2910010B1 (fr) * | 2006-12-19 | 2009-03-06 | Commissariat Energie Atomique | Procede de preparation d'un film organique a la surface d'un support solide dans des conditions non-electrochimiques, support solide ainsi obtenu et kit de preparation |
| FR2910007B1 (fr) * | 2006-12-19 | 2009-03-06 | Commissariat Energie Atomique | Procede de preparation d'un film organique a la surface d'un support solide dans des conditions non-electrochimiques, support solide ainsi obtenu et kit de preparation |
| CN101646734A (zh) * | 2007-01-24 | 2010-02-10 | 卡伯特公司 | 形成改性颜料的方法 |
| EP2129731A2 (en) * | 2007-02-27 | 2009-12-09 | Cabot Corporation | Inkjet ink compositions comprising multiple modified pigments |
| US8133311B2 (en) * | 2007-04-30 | 2012-03-13 | Cabot Corporation | Pigment dipsersions comprising functionalized non-polymeric dispersants |
| EP3483222A3 (en) | 2007-08-23 | 2019-08-07 | Sensient Colors LLC | Self-dispersed pigments and methods for making and using the same |
| WO2009075802A2 (en) * | 2007-12-07 | 2009-06-18 | Cabot Corporation | Method of preparing a pigment composition |
| US20090155508A1 (en) | 2007-12-14 | 2009-06-18 | Pactiv Corporation | Encapsulated Activated Carbon and the Preparation Thereof |
| CN101970586B (zh) * | 2008-03-17 | 2014-08-20 | 卡伯特公司 | 具有降低的磷酸根释放的改性颜料以及得自其的分散体和喷墨油墨组合物 |
| US8129448B2 (en) * | 2008-12-18 | 2012-03-06 | Cabot Corporation | Method of preparing polymer modified pigments |
| JP2012514683A (ja) * | 2009-01-09 | 2012-06-28 | キャボット コーポレイション | 低減された導電率増加を有する改質顔料含有インクジェットインク組成物 |
| US20100227162A1 (en) * | 2009-03-03 | 2010-09-09 | Abhimanyu Onkar Patil | Atom transfer radical polymerization (ATRP) based inorganic polymer structures |
| EP2417202A2 (en) | 2009-04-07 | 2012-02-15 | Sensient Colors LLC | Self-dispersing particles and methods for making and using the same |
| CN101870464B (zh) * | 2009-04-24 | 2013-05-08 | 清华大学 | 碳纳米管胶囊及制备方法,其复合材料及制备方法 |
| US9644042B2 (en) | 2010-12-17 | 2017-05-09 | Carnegie Mellon University | Electrochemically mediated atom transfer radical polymerization |
| US8435707B2 (en) | 2011-06-16 | 2013-05-07 | Cabot Corporation | Toner additive comprising carbon-silica dual phase particles |
| US9546286B2 (en) | 2011-07-22 | 2017-01-17 | Cabot Corporation | High resistivity coating compositions having unique percolation behavior, and electrostatic image developing systems and components thereof incorporating same |
| US20140275420A1 (en) | 2011-08-22 | 2014-09-18 | Carnegie Mellon University | Atom transfer radical polymerization under biologically compatible conditions |
| JP5900734B2 (ja) * | 2011-12-06 | 2016-04-06 | 株式会社豊田中央研究所 | 樹脂複合材料およびその製造方法 |
| US9533297B2 (en) | 2012-02-23 | 2017-01-03 | Carnegie Mellon University | Ligands designed to provide highly active catalyst complexes |
| KR101391825B1 (ko) * | 2012-05-21 | 2014-05-12 | (주)고딘테크 | 그라핀-공중합체 나노복합체 제조 방법 |
| WO2014012597A1 (en) * | 2012-07-20 | 2014-01-23 | Hewlett-Packard Indigo B.V. | Polymerically coated metallic pigment particles, method for providing them and electrostatic inks |
| US20140120339A1 (en) | 2012-10-31 | 2014-05-01 | Cabot Corporation | Porous carbon monoliths templated by pickering emulsions |
| ES2688532T3 (es) | 2013-01-18 | 2018-11-05 | Basf Se | Composiciones de recubrimiento a base de dispersión acrílica |
| EP3038836B1 (en) | 2013-08-28 | 2021-10-06 | Hewlett-Packard Development Company, L.P. | Printable recording media |
| TWI519608B (zh) * | 2013-12-27 | 2016-02-01 | 財團法人工業技術研究院 | 混成碳黑、及包含其之塗佈組合物與遮光材料 |
| WO2015168327A1 (en) | 2014-04-29 | 2015-11-05 | Rennovia Inc. | Carbon black based shaped porous products |
| US11253839B2 (en) | 2014-04-29 | 2022-02-22 | Archer-Daniels-Midland Company | Shaped porous carbon products |
| KR102405453B1 (ko) * | 2014-07-15 | 2022-06-03 | 이머리스 그래파이트 앤드 카본 스위춰랜드 리미티드 | 친수성 표면 개질된 탄소질 미립자 물질 |
| US9982070B2 (en) | 2015-01-12 | 2018-05-29 | Carnegie Mellon University | Aqueous ATRP in the presence of an activator regenerator |
| TWI565655B (zh) * | 2015-09-25 | 2017-01-11 | 財團法人工業技術研究院 | 混成碳黑與塗佈組合物 |
| US10722867B2 (en) | 2015-10-28 | 2020-07-28 | Archer-Daniels-Midland Company | Porous shaped carbon products |
| US10464048B2 (en) | 2015-10-28 | 2019-11-05 | Archer-Daniels-Midland Company | Porous shaped metal-carbon products |
| WO2018132582A1 (en) | 2017-01-12 | 2018-07-19 | Carnegie Mellon University | Surfactant assisted formation of a catalyst complex for emulsion atom transfer radical polymerization processes |
| US11185845B1 (en) | 2017-12-07 | 2021-11-30 | U.S. Government As Represented By The Secretary Of The Army | Water extractable microcapsules of activated carbon, super activated carbon, and other adsorptive and reactive materials |
| JP6964646B2 (ja) * | 2018-05-16 | 2021-11-10 | 旭化成株式会社 | セルロース含有樹脂組成物の製造方法 |
| JP6796107B2 (ja) * | 2018-05-16 | 2020-12-02 | 旭化成株式会社 | セルロース含有樹脂組成物の製造方法 |
| JP7781073B2 (ja) | 2020-05-18 | 2025-12-05 | アーチャー－ダニエルズ－ミッドランド カンパニー | グリセロールの水素化分解プロセス |
Family Cites Families (70)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2439442A (en) | 1943-02-06 | 1948-04-13 | Cabot Godfrey L Inc | Process of making hydrophilic carbon black |
| US2502254A (en) | 1945-12-07 | 1950-03-28 | Ici Ltd | Manufacture of pigments |
| US2514236A (en) | 1948-03-12 | 1950-07-04 | Ici Ltd | Manufacture of pigments |
| US2867540A (en) | 1955-12-30 | 1959-01-06 | Monsanto Chemicals | Modified carbon black product and process |
| DE1082045B (de) | 1958-01-30 | 1960-05-19 | Hoechst Ag | Faerbung von plastischen Massen |
| GB910309A (en) | 1958-07-22 | 1962-11-14 | Dunlop Rubber Co | Rubber compositions |
| US3043708A (en) | 1958-07-22 | 1962-07-10 | Dunlop Rubber Co | Modified carbon black |
| US3335020A (en) | 1964-03-02 | 1967-08-08 | Huber Corp J M | Modified carbon blacks |
| US3479300A (en) | 1965-10-22 | 1969-11-18 | Cabot Corp | Carbonaceous products |
| US3471439A (en) | 1966-03-10 | 1969-10-07 | Amicon Corp | Reinforcing filler |
| US4014844A (en) | 1970-06-26 | 1977-03-29 | Agence Nationale De Valorisation De La Recherche (Anvar) | Process for grafting polymers on carbon black through free radical mechanism |
| US3755244A (en) | 1971-06-02 | 1973-08-28 | Hercules Inc | Polyolefin pigment dispersions |
| US3884871A (en) | 1973-06-29 | 1975-05-20 | Nl Industries Inc | Process for coating pigment particles with organic polymers |
| GB1589960A (en) | 1977-06-02 | 1981-05-20 | Bayer Ag | Dyestuff formulations |
| DE2850662A1 (de) | 1978-11-22 | 1980-06-12 | Bayer Ag | Polyaetherfarbstoffe, praeparationen dieser farbstoffe, deren herstellung sowie deren verwendung |
| GB2036779B (en) | 1978-11-22 | 1983-03-09 | Bayer Ag | Polyether disazo dyestuffs |
| DE3049180A1 (de) | 1980-12-24 | 1982-07-29 | Cassella Ag, 6000 Frankfurt | Wasserunloesliche monoazofarbstoffe, ihre herstellung und ihre verwendung |
| US4758243A (en) | 1986-05-27 | 1988-07-19 | Milliken Research Corporation | Process for coloring polyester shaped articles |
| US4880857A (en) | 1986-12-17 | 1989-11-14 | Nippon Shokubai Kagaku Kogyo Co., Ltd. | Carbon black-graft polymer, method for production thereof, and use thereof |
| US4871371A (en) | 1988-10-24 | 1989-10-03 | Milliken Research Corporation | Tint compositions useful for providing coloration to aqueous and non-aqueous liquids |
| US4946509A (en) | 1989-05-23 | 1990-08-07 | Sun Chemical Corporation | Diarylide pigment compositions |
| EP0437105B1 (en) | 1990-01-08 | 1996-11-13 | Milliken Research Corporation | Intermediates and colorants having primary hydroxyl enriched poly(oxyalkylene) moieties and their preparation |
| JPH0428776A (ja) | 1990-05-24 | 1992-01-31 | Mitsubishi Kasei Corp | インクジェット用記録液 |
| US5281261A (en) | 1990-08-31 | 1994-01-25 | Xerox Corporation | Ink compositions containing modified pigment particles |
| JP3004062B2 (ja) | 1991-02-06 | 2000-01-31 | 株式会社日本触媒 | インキ及びインキ用着色剤 |
| CA2050019A1 (en) | 1991-08-27 | 1993-02-28 | John Bery Hines | Colorants and intermediates therefor having branched poly(oxyalkylene) moieties, and their manufacture |
| ZA933185B (en) * | 1992-05-08 | 1994-05-23 | Dick Co Ab | Encapsulated magnetic particles pigments and carbon black compositions and methods related thereto |
| US5298356A (en) | 1992-11-13 | 1994-03-29 | Eastman Kodak Company | Toner composition with elastomeric thermoplastic polymer and process of preparing |
| IL116376A (en) | 1994-12-15 | 2001-03-19 | Cabot Corp | Aqueous ink jet ink compositions containing modified carbon products |
| IL116379A (en) * | 1994-12-15 | 2003-12-10 | Cabot Corp | Aqueous inks and coatings containing modified carbon products |
| US5554739A (en) | 1994-12-15 | 1996-09-10 | Cabot Corporation | Process for preparing carbon materials with diazonium salts and resultant carbon products |
| US5807494A (en) | 1994-12-15 | 1998-09-15 | Boes; Ralph Ulrich | Gel compositions comprising silica and functionalized carbon products |
| US5559169A (en) | 1994-12-15 | 1996-09-24 | Cabot Corporation | EPDM, HNBR and Butyl rubber compositions containing carbon black products |
| IL116377A (en) | 1994-12-15 | 2003-05-29 | Cabot Corp | Reaction of carbon black with diazonium salts, resultant carbon black products and their uses |
| US5571311A (en) | 1994-12-15 | 1996-11-05 | Cabot Corporation | Ink jet ink formulations containing carbon black products |
| IL116552A (en) | 1995-01-10 | 2001-09-13 | Cabot Corp | Carbon black compositions, polymer compositions including the carbon black compositions and articles of manufacture including the polymer compositions |
| US5869550A (en) | 1995-05-22 | 1999-02-09 | Cabot Corporation | Method to improve traction using silicon-treated carbon blacks |
| JP3512129B2 (ja) * | 1995-06-14 | 2004-03-29 | 株式会社日本触媒 | 着色剤組成物 |
| US5952429A (en) * | 1995-06-14 | 1999-09-14 | Nippon Shokubai Co., Ltd. | Carbon black graft polymer, method for production thereof, and use thereof |
| US6017584A (en) | 1995-07-20 | 2000-01-25 | E Ink Corporation | Multi-color electrophoretic displays and materials for making the same |
| JP3460762B2 (ja) * | 1995-10-30 | 2003-10-27 | 三菱化学株式会社 | 絶縁性ブラックマトリックス用カーボンブラック |
| US5747559A (en) | 1995-11-22 | 1998-05-05 | Cabot Corporation | Polymeric compositions |
| JP3501436B2 (ja) * | 1996-02-15 | 2004-03-02 | 株式会社リコー | 処理カーボンブラック顔料および該顔料を含有する静電荷像現像用トナー |
| JPH09292703A (ja) | 1996-04-25 | 1997-11-11 | Mitsubishi Chem Corp | レーザーダイレクト湿し水不要感光性平版印刷版 |
| US6110994A (en) | 1996-06-14 | 2000-08-29 | Cabot Corporation | Polymeric products containing modified carbon products and methods of making and using the same |
| US5698016A (en) | 1996-06-14 | 1997-12-16 | Cabot Corporation | Compositions of modified carbon products and amphiphilic ions and methods of using the same |
| US5707432A (en) | 1996-06-14 | 1998-01-13 | Cabot Corporation | Modified carbon products and inks and coatings containing modified carbon products |
| KR100463354B1 (ko) * | 1996-06-14 | 2005-06-16 | 캐보트 코포레이션 | 개질탄소생성물및양친매성이온함유조성물 |
| US6069190A (en) * | 1996-06-14 | 2000-05-30 | Cabot Corporation | Ink compositions having improved latency |
| US5747562A (en) | 1996-06-14 | 1998-05-05 | Cabot Corporation | Ink and coating compositions containing silicon-treated carbon black |
| US5837045A (en) | 1996-06-17 | 1998-11-17 | Cabot Corporation | Colored pigment and aqueous compositions containing same |
| US6103782A (en) * | 1996-07-29 | 2000-08-15 | Marconi Data Systems, Inc. | Method of making dry pigment surface modified with polyethylene coating |
| JPH1053722A (ja) * | 1996-08-12 | 1998-02-24 | Yokohama Rubber Co Ltd:The | ゴム補強用表面処理カーボンブラックの製造方法 |
| JPH1090691A (ja) * | 1996-09-11 | 1998-04-10 | Natoko Paint Kk | 液晶用着色遮光スペーサーおよび液晶表示素子 |
| JPH1095943A (ja) * | 1996-09-24 | 1998-04-14 | Citizen Watch Co Ltd | 水性顔料系記録液 |
| US6197274B1 (en) | 1996-09-25 | 2001-03-06 | Cabot Corporation | Silica coated carbon blacks |
| US5930026A (en) | 1996-10-25 | 1999-07-27 | Massachusetts Institute Of Technology | Nonemissive displays and piezoelectric power supplies therefor |
| US5919855A (en) | 1997-02-11 | 1999-07-06 | Cabot Corporation | Use of modified carbon black in gas-phase polymerizations |
| US5783614A (en) | 1997-02-21 | 1998-07-21 | Copytele, Inc. | Polymeric-coated dielectric particles and formulation and method for preparing same |
| US5961804A (en) | 1997-03-18 | 1999-10-05 | Massachusetts Institute Of Technology | Microencapsulated electrophoretic display |
| US6017980A (en) * | 1997-03-27 | 2000-01-25 | Cabot Corporation | Elastomeric compounds incorporating metal-treated carbon blacks |
| US6020063A (en) * | 1997-07-31 | 2000-02-01 | Virginia Tech Intellectual Properties, Inc. | Composites of thermosetting resins and carbon fibers having polyhydroxyether sizings |
| US5932633A (en) | 1997-08-22 | 1999-08-03 | Copytele, Inc. | Method for making polymers-coated pigment particles using initiator-treated pigments |
| US5964935A (en) | 1997-08-22 | 1999-10-12 | Copytele, Inc. | Initiator-treated pigment particles and method for preparing same |
| US5990202A (en) | 1997-10-31 | 1999-11-23 | Hewlett-Packard Company | Dual encapsulation technique for preparing ink-jets inks |
| US6057384A (en) | 1997-10-31 | 2000-05-02 | Hewlett-Packard Company | Latex polymer blends for improving the permanence of ink-jet inks |
| US6103380A (en) * | 1998-06-03 | 2000-08-15 | Cabot Corporation | Particle having an attached halide group and methods of making the same |
| US6150433A (en) * | 1998-07-31 | 2000-11-21 | Hewlett-Packard Company | Ink-jet ink compositions containing modified macromolecular chromophores with covalently attached polymers |
| DE69918498T2 (de) * | 1998-07-31 | 2005-08-18 | Hewlett-Packard Development Co., L.P., Houston | Kovalente Fixierung von Polymeren an Makromolekülchromophoren durch nucleophile Substitution für den Tintenstrahldruck |
| US6479571B1 (en) | 2000-01-25 | 2002-11-12 | Cabot Corporation | Elastomeric compositions containing polymer coated carbon products and other pigments |
-
1999
- 1999-05-24 US US09/317,706 patent/US6458458B1/en not_active Expired - Lifetime
- 1999-10-08 CA CA002347093A patent/CA2347093C/en not_active Expired - Fee Related
- 1999-10-08 DE DE69932071T patent/DE69932071T2/de not_active Expired - Lifetime
- 1999-10-08 KR KR1020017004653A patent/KR100639724B1/ko not_active Expired - Fee Related
- 1999-10-08 AU AU64212/99A patent/AU6421299A/en not_active Abandoned
- 1999-10-08 EP EP99951860A patent/EP1124905B1/en not_active Expired - Lifetime
- 1999-10-08 WO PCT/US1999/023429 patent/WO2000022051A1/en not_active Ceased
- 1999-10-08 AT AT99951860T patent/ATE331000T1/de not_active IP Right Cessation
- 1999-10-08 ES ES99951860T patent/ES2262344T3/es not_active Expired - Lifetime
- 1999-10-08 JP JP2000575948A patent/JP2002527564A/ja not_active Withdrawn
-
2011
- 2011-12-20 JP JP2011278264A patent/JP2012072414A/ja active Pending
-
2014
- 2014-12-26 JP JP2014266662A patent/JP2015110785A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108864774A (zh) * | 2018-07-20 | 2018-11-23 | 江南大学 | 一种棉织物染色用反应性自分散纳米炭黑的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002527564A (ja) | 2002-08-27 |
| EP1124905B1 (en) | 2006-06-21 |
| DE69932071D1 (de) | 2006-08-03 |
| KR100639724B1 (ko) | 2006-10-30 |
| ATE331000T1 (de) | 2006-07-15 |
| ES2262344T3 (es) | 2006-11-16 |
| JP2015110785A (ja) | 2015-06-18 |
| KR20010085918A (ko) | 2001-09-07 |
| AU6421299A (en) | 2000-05-01 |
| DE69932071T2 (de) | 2006-11-23 |
| EP1124905A1 (en) | 2001-08-22 |
| WO2000022051A1 (en) | 2000-04-20 |
| CA2347093A1 (en) | 2000-04-20 |
| JP2012072414A (ja) | 2012-04-12 |
| US6458458B1 (en) | 2002-10-01 |
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