TWI422605B - 以二烯為主體之聚合物乳膠的氫化（二） - Google Patents
以二烯為主體之聚合物乳膠的氫化（二） Download PDFInfo
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- TWI422605B TWI422605B TW097148849A TW97148849A TWI422605B TW I422605 B TWI422605 B TW I422605B TW 097148849 A TW097148849 A TW 097148849A TW 97148849 A TW97148849 A TW 97148849A TW I422605 B TWI422605 B TW I422605B
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- Prior art keywords
- catalyst component
- latex
- weight
- polymer
- hydrogenation
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims description 79
- 229920000126 latex Polymers 0.000 title claims description 71
- 239000004816 latex Substances 0.000 title claims description 70
- 238000005984 hydrogenation reaction Methods 0.000 title claims description 69
- 150000001993 dienes Chemical class 0.000 title claims description 28
- 239000003054 catalyst Substances 0.000 claims description 96
- 238000000034 method Methods 0.000 claims description 63
- 239000000178 monomer Substances 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 239000006185 dispersion Substances 0.000 claims description 23
- 239000003960 organic solvent Substances 0.000 claims description 22
- 229920000459 Nitrile rubber Polymers 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 238000011065 in-situ storage Methods 0.000 claims description 15
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 14
- 229910052762 osmium Inorganic materials 0.000 claims description 12
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 12
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 11
- 150000002825 nitriles Chemical class 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 10
- VZCYOOQTPOCHFL-OWOJBTEDSA-N fumaric acid group Chemical group C(\C=C\C(=O)O)(=O)O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 10
- 229910052707 ruthenium Inorganic materials 0.000 claims description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 10
- 229920001577 copolymer Polymers 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000011574 phosphorus Substances 0.000 claims description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 239000001530 fumaric acid Substances 0.000 claims description 5
- 150000004678 hydrides Chemical class 0.000 claims description 5
- 229910052741 iridium Inorganic materials 0.000 claims description 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 5
- 239000011976 maleic acid Substances 0.000 claims description 5
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 4
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000007983 Tris buffer Substances 0.000 claims description 3
- 229910052785 arsenic Inorganic materials 0.000 claims description 3
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 3
- 150000004820 halides Chemical group 0.000 claims description 3
- 229910000510 noble metal Inorganic materials 0.000 claims description 3
- 229920001897 terpolymer Polymers 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 229940006460 bromide ion Drugs 0.000 claims description 2
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical group C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000005567 fluorenylene group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- VYOUONUEBBCXHG-UHFFFAOYSA-K methylsulfanylmethane ruthenium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3].CSC.CSC.CSC VYOUONUEBBCXHG-UHFFFAOYSA-K 0.000 claims 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims 1
- 150000003003 phosphines Chemical class 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 description 22
- -1 azabenzenes Chemical class 0.000 description 19
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- 239000000839 emulsion Substances 0.000 description 13
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 229910052783 alkali metal Inorganic materials 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 150000003863 ammonium salts Chemical class 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 8
- 239000010948 rhodium Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000004815 dispersion polymer Substances 0.000 description 7
- 229920001971 elastomer Polymers 0.000 description 7
- 239000005060 rubber Substances 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 238000007720 emulsion polymerization reaction Methods 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
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- 150000002466 imines Chemical class 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- NTUROZDXWLPVHB-UHFFFAOYSA-M sodium;3-diphenylphosphanylbenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NTUROZDXWLPVHB-UHFFFAOYSA-M 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 239000012018 catalyst precursor Substances 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
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- 238000004332 deodorization Methods 0.000 description 3
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- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
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- 159000000000 sodium salts Chemical class 0.000 description 3
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- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
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- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
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- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
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- 229910000071 diazene Inorganic materials 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 2
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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 2
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- QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 2
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- 239000011995 wilkinson's catalyst Substances 0.000 description 2
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- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
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- 125000000000 cycloalkoxy group Chemical group 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
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- IGBZOHMCHDADGY-UHFFFAOYSA-N ethenyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OC=C IGBZOHMCHDADGY-UHFFFAOYSA-N 0.000 description 1
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
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- 239000012074 organic phase Substances 0.000 description 1
- 150000002907 osmium Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
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- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
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- 125000005385 peroxodisulfate group Chemical group 0.000 description 1
- WJIBZZVTNMAURL-UHFFFAOYSA-N phosphane;rhodium Chemical group P.[Rh] WJIBZZVTNMAURL-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
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- 229940096992 potassium oleate Drugs 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
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- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
- 159000000008 strontium salts Chemical class 0.000 description 1
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- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/04—Reduction, e.g. hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/02—Hydrogenation
-
- 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
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07123385A EP2072535A1 (en) | 2007-12-17 | 2007-12-17 | Hydrogenation of diene-based polymer latex |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200940576A TW200940576A (en) | 2009-10-01 |
| TWI422605B true TWI422605B (zh) | 2014-01-11 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW097148849A TWI422605B (zh) | 2007-12-17 | 2008-12-16 | 以二烯為主體之聚合物乳膠的氫化（二） |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7799872B2 (enExample) |
| EP (2) | EP2072535A1 (enExample) |
| JP (1) | JP5525724B2 (enExample) |
| KR (1) | KR20090065456A (enExample) |
| CN (1) | CN101463098B (enExample) |
| BR (1) | BRPI0809598A2 (enExample) |
| CA (1) | CA2646847A1 (enExample) |
| TW (1) | TWI422605B (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2289947A1 (en) * | 2009-08-26 | 2011-03-02 | University Of Waterloo | Nano-sized hydrogenated diene-based latex particles |
| TWI526491B (zh) * | 2010-08-13 | 2016-03-21 | 朗盛公司 | 異烯烴與二烯烴的官能化共聚物、及它們作為增容劑的用途 |
| RU2470942C1 (ru) * | 2011-06-22 | 2012-12-27 | ОТКРЫТОЕ АКЦИОНЕРНОЕ ОБЩЕСТВО "СИБУР Холдинг" | Способ гидрирования бутадиен-нитрильного каучука |
| EP2676971B1 (en) * | 2012-06-22 | 2015-04-08 | University Of Waterloo | Hydrogenation of a diene-based polymer latex |
| EP2676970B1 (en) | 2012-06-22 | 2015-04-08 | University Of Waterloo | Hydrogenation of diene-based polymers |
| JP6414937B2 (ja) * | 2016-12-22 | 2018-10-31 | 株式会社レヂテックス | 水素化天然ゴムラテックスの製造方法 |
| CN110540609B (zh) * | 2018-05-28 | 2022-12-23 | 王辉 | 制备氢化二烯基纳米乳液的方法和双子表面活性剂的用途 |
| CN111019018B (zh) * | 2019-12-25 | 2022-03-04 | 山东京博石油化工有限公司 | 一种氢化二烯烃基橡胶的制备方法 |
| CN111303317B (zh) * | 2020-04-01 | 2022-04-22 | 山东京博中聚新材料有限公司 | 一种共轭二烯烃加氢胶乳制备氢化共聚物的方法 |
| CN114149520B (zh) * | 2021-12-09 | 2023-03-24 | 北京化工大学 | 一锅法制备氢化丁腈胶乳的方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1358201A (zh) * | 1999-05-27 | 2002-07-10 | 巴斯福股份公司 | 聚合物中烯属不饱和双键的选择性氢化 |
| CN1834112A (zh) * | 2005-03-18 | 2006-09-20 | 兰科瑟斯有限公司 | 二烯基聚合物胶乳的氢化 |
Family Cites Families (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3454644A (en) | 1966-05-09 | 1969-07-08 | Shell Oil Co | Homogeneous hydrogenation process employing a complex of ruthenium or osmium as catalyst |
| EP0061337A1 (en) * | 1981-03-25 | 1982-09-29 | Johnson Matthey Public Limited Company | Catalytic process |
| US4452950A (en) | 1983-02-22 | 1984-06-05 | The Goodyear Tire & Rubber Company | Process for hydrogenation of carbon-carbon double bonds in an unsaturated polymer in latex form |
| DE3433392A1 (de) | 1984-09-12 | 1986-03-20 | Bayer Ag, 5090 Leverkusen | Hydrierung nitrilgruppenhaltiger ungesaettigter polymerer |
| DE3803450A1 (de) | 1988-02-05 | 1989-08-17 | Hoechst Ag | Emissionsarme dispersionsfarben, anstrichmittel und kunststoffdispersionsputze sowie verfahren zu ihrer herstellung |
| DE3834734A1 (de) | 1988-10-12 | 1990-04-19 | Basf Ag | Verfahren zur herstellung von polymerisaten aus olefinisch ungesaettigten monomeren |
| JP2732273B2 (ja) | 1988-12-29 | 1998-03-25 | 日本ゼオン株式会社 | ニトリル基含有水素化重合体の製造方法 |
| DE3902103A1 (de) | 1989-01-25 | 1990-08-02 | Roehm Gmbh | Bindemittel fuer waessrige glanzfarben |
| US5021649A (en) | 1989-03-28 | 1991-06-04 | Canon Kabushiki Kaisha | Relief diffraction grating encoder |
| US5039737A (en) | 1990-02-22 | 1991-08-13 | The Goodyear Tire & Rubber Company/Olin Corp. | Ozonolysis of hydrogenated latices |
| US5057581A (en) | 1990-05-02 | 1991-10-15 | University Of Waterloo | Polymer hydrogenation process |
| JPH04323205A (ja) * | 1991-04-23 | 1992-11-12 | Mitsubishi Kasei Corp | ニトリル基含有不飽和共重合体の水素化方法 |
| CA2091128C (en) | 1992-03-08 | 1999-07-27 | Michael A. Taylor | Removal of organic volatiles from polymer solutions and dispersions |
| DE4213965A1 (de) | 1992-04-29 | 1993-11-04 | Basf Ag | Waessrige polymerisatdispersion |
| DE4213964A1 (de) | 1992-04-29 | 1993-11-04 | Basf Ag | Waessrige polymerisatdispersionen |
| DE4213967A1 (de) | 1992-04-29 | 1993-11-04 | Basf Ag | Waessrige polymerisatdispersion |
| DE4213968A1 (de) | 1992-04-29 | 1993-11-04 | Basf Ag | Waessrige polymerisatdispersion |
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2007
- 2007-12-17 EP EP07123385A patent/EP2072535A1/en not_active Withdrawn
-
2008
- 2008-12-11 EP EP08171276.2A patent/EP2072538B1/en active Active
- 2008-12-16 TW TW097148849A patent/TWI422605B/zh active
- 2008-12-16 BR BRPI0809598-1A patent/BRPI0809598A2/pt not_active IP Right Cessation
- 2008-12-16 KR KR1020080127968A patent/KR20090065456A/ko not_active Ceased
- 2008-12-16 US US12/335,978 patent/US7799872B2/en active Active
- 2008-12-16 CA CA002646847A patent/CA2646847A1/en not_active Abandoned
- 2008-12-16 JP JP2008320193A patent/JP5525724B2/ja active Active
- 2008-12-17 CN CN2008101840896A patent/CN101463098B/zh active Active
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| CN1358201A (zh) * | 1999-05-27 | 2002-07-10 | 巴斯福股份公司 | 聚合物中烯属不饱和双键的选择性氢化 |
| CN1834112A (zh) * | 2005-03-18 | 2006-09-20 | 兰科瑟斯有限公司 | 二烯基聚合物胶乳的氢化 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2072538B1 (en) | 2014-02-26 |
| US20090281248A1 (en) | 2009-11-12 |
| JP2009144160A (ja) | 2009-07-02 |
| CN101463098B (zh) | 2012-08-22 |
| KR20090065456A (ko) | 2009-06-22 |
| EP2072538A1 (en) | 2009-06-24 |
| JP5525724B2 (ja) | 2014-06-18 |
| BRPI0809598A2 (pt) | 2011-05-17 |
| CN101463098A (zh) | 2009-06-24 |
| EP2072535A1 (en) | 2009-06-24 |
| CA2646847A1 (en) | 2009-06-17 |
| TW200940576A (en) | 2009-10-01 |
| US7799872B2 (en) | 2010-09-21 |
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