JP2015526542A - ジエン系ポリマーラテックスの水素化 - Google Patents
ジエン系ポリマーラテックスの水素化 Download PDFInfo
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- JP2015526542A JP2015526542A JP2015517869A JP2015517869A JP2015526542A JP 2015526542 A JP2015526542 A JP 2015526542A JP 2015517869 A JP2015517869 A JP 2015517869A JP 2015517869 A JP2015517869 A JP 2015517869A JP 2015526542 A JP2015526542 A JP 2015526542A
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- JP
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- Prior art keywords
- hydrogenation
- catalyst
- alkyl
- aryl
- group
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract description 88
- 150000001993 dienes Chemical class 0.000 title claims abstract description 48
- 238000005984 hydrogenation reaction Methods 0.000 title claims description 91
- 229920000126 latex Polymers 0.000 title abstract description 47
- 239000004816 latex Substances 0.000 title abstract description 45
- 239000003054 catalyst Substances 0.000 claims abstract description 77
- 238000000034 method Methods 0.000 claims abstract description 73
- 239000003960 organic solvent Substances 0.000 claims abstract description 25
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 12
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052762 osmium Inorganic materials 0.000 claims abstract description 8
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003446 ligand Substances 0.000 claims description 34
- 239000000178 monomer Substances 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 230000008569 process Effects 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 229920001577 copolymer Polymers 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 239000007900 aqueous suspension Substances 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 8
- 125000000129 anionic group Chemical group 0.000 claims description 7
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 6
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 5
- 125000005110 aryl thio group Chemical group 0.000 claims description 5
- 125000000962 organic group Chemical group 0.000 claims description 5
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 5
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 4
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000001905 inorganic group Chemical group 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000000725 suspension Substances 0.000 abstract description 17
- 239000002245 particle Substances 0.000 abstract description 7
- 239000012736 aqueous medium Substances 0.000 abstract description 6
- UMDKEXZDYVKYRU-UHFFFAOYSA-N [Bi].[C].[C] Chemical compound [Bi].[C].[C] UMDKEXZDYVKYRU-UHFFFAOYSA-N 0.000 abstract 1
- -1 azines Chemical class 0.000 description 41
- 238000006116 polymerization reaction Methods 0.000 description 29
- 229920000459 Nitrile rubber Polymers 0.000 description 25
- 150000002148 esters Chemical class 0.000 description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 15
- 239000000499 gel Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
- 238000005649 metathesis reaction Methods 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 11
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 229940018557 citraconic acid Drugs 0.000 description 10
- 239000003995 emulsifying agent Substances 0.000 description 10
- 239000010948 rhodium Substances 0.000 description 10
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 150000005690 diesters Chemical class 0.000 description 9
- 150000002431 hydrogen Chemical class 0.000 description 9
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 9
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 150000002825 nitriles Chemical class 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 7
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 238000011065 in-situ storage Methods 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 150000002763 monocarboxylic acids Chemical class 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 238000006555 catalytic reaction Methods 0.000 description 6
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 6
- 229910000071 diazene Inorganic materials 0.000 description 6
- 238000007720 emulsion polymerization reaction Methods 0.000 description 6
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 125000005907 alkyl ester group Chemical group 0.000 description 5
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 239000011976 maleic acid Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 229910052703 rhodium Inorganic materials 0.000 description 5
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 150000003568 thioethers Chemical class 0.000 description 5
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 5
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 150000002466 imines Chemical class 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000010526 radical polymerization reaction Methods 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000011734 sodium 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
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical group [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical group SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 150000007860 aryl ester derivatives Chemical class 0.000 description 3
- 235000010323 ascorbic acid Nutrition 0.000 description 3
- 239000011668 ascorbic acid Substances 0.000 description 3
- 229960005070 ascorbic acid Drugs 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
- 150000001718 carbodiimides Chemical group 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000012018 catalyst precursor Substances 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 125000004966 cyanoalkyl group Chemical group 0.000 description 3
- 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 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 238000004332 deodorization Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 239000012948 isocyanate Chemical group 0.000 description 3
- 150000002513 isocyanates Chemical group 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000002560 nitrile group Chemical group 0.000 description 3
- LJDZFAPLPVPTBD-UHFFFAOYSA-N nitroformic acid Chemical group OC(=O)[N+]([O-])=O LJDZFAPLPVPTBD-UHFFFAOYSA-N 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- MYAJTCUQMQREFZ-UHFFFAOYSA-K tppts Chemical compound [Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC=CC(P(C=2C=C(C=CC=2)S([O-])(=O)=O)C=2C=C(C=CC=2)S([O-])(=O)=O)=C1 MYAJTCUQMQREFZ-UHFFFAOYSA-K 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical compound CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- DETXZQGDWUJKMO-UHFFFAOYSA-N 2-hydroxymethanesulfonic acid Chemical compound OCS(O)(=O)=O DETXZQGDWUJKMO-UHFFFAOYSA-N 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 2
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 2
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- DAFQZPUISLXFBF-UHFFFAOYSA-N tetraoxathiolane 5,5-dioxide Chemical compound O=S1(=O)OOOO1 DAFQZPUISLXFBF-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- FICPQAZLPKLOLH-UHFFFAOYSA-N tricyclohexyl phosphite Chemical compound C1CCCCC1OP(OC1CCCCC1)OC1CCCCC1 FICPQAZLPKLOLH-UHFFFAOYSA-N 0.000 description 1
- AVYPTBDUFIEJDP-UHFFFAOYSA-N tricyclohexylstibane Chemical compound C1CCCCC1[Sb](C1CCCCC1)C1CCCCC1 AVYPTBDUFIEJDP-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- PORFVJURJXKREL-UHFFFAOYSA-N trimethylstibine Chemical compound C[Sb](C)C PORFVJURJXKREL-UHFFFAOYSA-N 0.000 description 1
- HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-UHFFFAOYSA-N 0.000 description 1
- SJHCUXCOGGKFAI-UHFFFAOYSA-N tripropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC(C)C SJHCUXCOGGKFAI-UHFFFAOYSA-N 0.000 description 1
- NZIQBDROTUFRHZ-UHFFFAOYSA-N tritert-butyl phosphite Chemical compound CC(C)(C)OP(OC(C)(C)C)OC(C)(C)C NZIQBDROTUFRHZ-UHFFFAOYSA-N 0.000 description 1
- 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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- 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
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- 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
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/12—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated with nitriles
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- 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
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
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Abstract
Description
Mはオスミウムまたはルテニウムであり、
X1およびX2は、同一であるかまたは異なるアニオン性リガンドであり、
Lは、リガンド、好ましくは無電荷の電子供与体であり、
Yは、酸素(O)、イオウ(S)、N-R1基またはP-R1基であり、ここで、R1は、アルキル、シクロアルキル、アルケニル、アルキニル、アリール、アルコキシ、アルケニルオキシ、アルキニルオキシ、アリールオキシ、アルコキシカルボニル、アルキルアミノ、アルキルチオ、アリールチオ、アルキルスルホニルまたはアルキルスルフィニル基であり、それらは各場合、場合により1つもしくは複数のアルキル、ハロゲン、アルコキシ、アリールまたはヘテロアリール基により置換されていてよく、
R2、R3、R4およびR5は、同一であるかまたは異なり、各々水素または有機もしくは無機の基であり、ならびに
R6は、水素またはアルキル、アルケニル、アルキニルもしくはアリール基である)
の触媒の存在下で水素化する工程を含み、一般式(A)のそのような触媒が、固体形態でジエン系ポリマーの水性懸濁液に添加されることを特徴とする、ジエン系ポリマー中の炭素-炭素二重結合を選択的に水素化する方法を提供する。
本発明による方法は、一般式(A)
Mはオスミウムまたはルテニウムであり、
X1およびX2は、同一であるかまたは異なるアニオン性リガンドであり、
Lは、リガンド、好ましくは無電荷の電子供与体であり、
Yは、酸素(O)、イオウ(S)、N-R1基またはP-R1基であり、ここで、R1は、アルキル、シクロアルキル、アルケニル、アルキニル、アリール、アルコキシ、アルケニルオキシ、アルキニルオキシ、アリールオキシ、アルコキシカルボニル、アルキルアミノ、アルキルチオ、アリールチオ、アルキルスルホニルまたはアルキルスルフィニル基であり、それらは各場合、場合により1つもしくは複数のアルキル、ハロゲン、アルコキシ、アリールまたはヘテロアリール基により置換されていてよく、
R2、R3、R4およびR5は、同一であるかまたは異なり、各々水素または有機もしくは無機の基であり、ならびに
R6は、水素またはアルキル、アルケニル、アルキニルもしくはアリール基である)
を有する少なくとも1種の触媒の存在下で実施される。
一般式(A)の触媒において、X1およびX2は、同一であるかまたは異なり、アニオン性リガンドを表す。
一般式(A)において、記号Lはリガンドを表し、好ましくは無電荷の電子供与体である。
R12、R13およびR14は、同一であるかまたは異なり、さらにより好ましくは同一であり、C1〜C20アルキル、好ましくはメチル、エチル、n-プロピル、イソプロピル、n-ブチル、sec-ブチル、tert-ブチル、n-ペンチル、1-メチルブチル、2-メチルブチル、3-メチルブチル、ネオペンチル、1-エチルプロピル、n-ヘキシル、またはネオフェニル、C3〜C8-シクロアルキル、好ましくはシクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、シクロヘプチルまたはシクロオクチル、C1〜C20アルコキシ、置換されたもしくは非置換のC6〜C20アリール、好ましくはフェニル、ビフェニル、ナフチル、フェナントレニル、アントラセニル、トリル、2,6-ジメチルフェニル、またはトリフルオロメチル、C6〜C20アリールオキシ、環中に少なくとも1種のヘテロ原子を有するC2〜C20ヘテロアリール、環中に少なくとも1種のヘテロ原子を有するC2〜C20ヘテロシクリルまたはハロゲン、好ましくはフルオロを表すことができ;
Lが、一般式(IIf)のホスフィンを、一般式(A)または(B)における電子供与性リガンドとして表す場合、そのようなホスフィンは、好ましくは、PPh3、P(p-Tol)3、P(o-Tol)3、PPh(CH3)2、P(CF3)3、P(p-FC6H4)3、P(p-CF3C6H4)3、P(C6H4-SO3Na)3、P(CH2C6H4-SO3Na)3、P(イソプロピル)3、P(CHCH3(CH2CH3))3、P(シクロペンチル)3、P(シクロヘキシル)3、P(ネオペンチル)3またはP(ネオフェニル)3を表し、その場合Phはフェニルを意味し、Tolはトリルを意味する)を有する。
R8、R9、R10およびR11は同一であるかまたは異なり、水素、直鎖もしくは分岐C1〜C30-アルキル、C3〜C20-シクロアルキル、C2〜C20-アルケニル、C2〜C20-アルキニル、C6〜C24-アリール、C7〜C25-アルカリール、C2〜C20ヘテロアリール、C2〜C20ヘテロシクリル、C1〜C20-アルコキシ、C2〜C20-アルケニルオキシ、C2〜C20-アルキニルオキシ、C6〜C20-アリールオキシ、C2〜C20-アルコキシカルボニル、C1〜C20-アルキルチオ、C6〜C20-アリールチオ、-Si(R)3、-O-Si(R)3、-O-C(=O)R、C(=O)R、-C(=O)N(R)2、-NR-C(=O)-N(R)2、-SO2N(R)2、-S(=O)R、-S(=O)2R、-O-S(=O)2R、ハロゲン、ニトロまたはシアノを表し;ここで、R8、R9、R10およびR11の意味に関して、上のものが現れる全ての場合、R基は同一であるかまたは異なり、水素、アルキル、シクロアルキル、アルケニル、アルキニル、アリールまたはヘテロアリールを表す)に対応する構造を有する。
R8およびR9は同一であるかまたは異なり、水素、C6〜C24-アリール、より好ましくはフェニル、直鎖もしくは分岐C1〜C10-アルキル、より好ましくはメチル、エチル、n-プロピル、i-プロピル、n-ブチル、sec-ブチル、i-ブチルまたはtert-ブチルを表し、あるいはそれらが結合している炭素原子と一緒になってシクロアルキルまたはアリール構造を形成する。
R10およびR11は同一であるかまたは異なり、好ましくは、直鎖もしくは分岐C1〜C10-アルキル、より好ましくはi-プロピルまたはネオペンチル、C3〜C10-シクロアルキル、より好ましくはアダマンチル、置換されたもしくは非置換のC6〜C24-アリール、より好ましくはフェニル、2,6-ジイソプロピルフェニル、2,6-ジメチルフェニル、または2,4,6-トリメチルフェニル、C1〜C10-アルキルスルホネート、またはC6〜C10-アリールスルホネートを表す。
R8およびR9は同一であるかまたは異なり、水素、C6〜C24-アリール、より好ましくはフェニル、直鎖もしくは分岐C1〜C10-アルキル、より好ましくはメチル、エチル、n-プロピル、i-プロピル、n-ブチル、sec-ブチル、およびi-ブチルを表し、またはそれらが結合している炭素原子と一緒になってシクロアルキルもしくはアリール構造を形成し、ならびに
R10およびR11は同一であるかまたは異なり、好ましくは、直鎖もしくは分岐C1〜C10-アルキル、より好ましくはi-プロピルまたはネオペンチル、C3〜C10-シクロアルキル、より好ましくはアダマンチル、置換されたもしくは非置換のC6〜C24-アリール、より好ましくはフェニル、2,6-ジイソプロピルフェニル、2,6-ジメチルフェニル、または2,4,6-トリメチルフェニル、C1〜C10-アルキルスルホネート、またはC6〜C10-アリールスルホネートを表す。
本発明の水素化方法に適当な基質は、原理的に「ラテックス」とも呼ばれるジエン系ポリマーの全ての水性懸濁液である。そのようなジエン系ポリマーは、炭素-炭素二重結合を含有する。これらのラテックスは、水性モノマーエマルション(一次懸濁液)のフリーラジカル重合により調製された懸濁液と、ポリマーがどのような方法または経路によって調製されたにしろ、次に水性懸濁液形態に変換されたもの(二次懸濁液)の両方を含む。用語「水性懸濁液」は、原理的に、マイクロカプセルの懸濁液も含む。
- マレイン酸モノアルキルエステル、好ましくはマレイン酸モノメチル、マレイン酸モノエチル、マレイン酸モノプロピル、およびマレイン酸モノn-ブチル;
- マレイン酸モノシクロアルキルエステル、好ましくはマレイン酸モノシクロペンチル、マレイン酸モノシクロヘキシル、およびマレイン酸モノシクロヘプチル;
- マレイン酸モノアルキルシクロアルキルエステル、好ましくはマレイン酸モノメチルシクロペンチル、およびマレイン酸モノエチルシクロヘキシル;
- マレイン酸モノアリールエステル、好ましくはマレイン酸モノフェニル;
- マレイン酸モノベンジルエステル、好ましくはマレイン酸モノベンジル;
- フマル酸モノアルキルエステル、好ましくはフマル酸モノメチル、フマル酸モノエチル、フマル酸モノプロピル、およびフマル酸モノn-ブチル;
- フマル酸モノシクロアルキルエステル、好ましくはフマル酸モノシクロペンチル、フマル酸モノシクロヘキシル、およびフマル酸モノシクロヘプチル;
- フマル酸モノアルキルシクロアルキルエステル、好ましくはフマル酸モノメチルシクロペンチル、およびフマル酸モノエチルシクロヘキシル;
- フマル酸モノアリールエステル、好ましくはフマル酸モノフェニル;
- フマル酸モノベンジルエステル、好ましくはフマル酸モノベンジル;
- シトラコン酸モノアルキルエステル、好ましくはシトラコン酸モノメチル、シトラコン酸モノエチル、シトラコン酸モノプロピル、およびシトラコン酸モノn-ブチル;
- シトラコン酸モノシクロアルキルエステル、好ましくはシトラコン酸モノシクロペンチル、シトラコン酸モノシクロヘキシル、およびシトラコン酸モノシクロヘプチル;
- シトラコン酸モノアルキルシクロアルキルエステル、好ましくはシトラコン酸モノメチルシクロペンチル、およびシトラコン酸モノエチルシクロヘキシル;
- シトラコン酸モノアリールエステル、好ましくはシトラコン酸モノフェニル;
- シトラコン酸モノベンジルエステル、好ましくはシトラコン酸モノベンジル;
- イタコン酸モノアルキルエステル、好ましくはイタコン酸モノメチル、イタコン酸モノエチル、イタコン酸モノプロピル、およびイタコン酸モノn-ブチル;
- イタコン酸モノシクロアルキルエステル、好ましくはイタコン酸モノシクロペンチル、イタコン酸モノシクロヘキシル、およびイタコン酸モノシクロヘプチル;
- イタコン酸モノアルキルシクロアルキルエステル、好ましくはイタコン酸モノメチルシクロペンチル、およびイタコン酸モノエチルシクロヘキシル;
- イタコン酸モノアリールエステル、好ましくはイタコン酸モノフェニル;
- イタコン酸モノベンジルエステル、好ましくはイタコン酸モノベンジル
が挙げられる。
本発明の方法に供することができるポリマーが、1種または複数の共役ジエンの反復単位だけでなく、1種または複数のさらなる共重合可能なモノマーの反復単位も含む場合、共役ジエンと他の共重合可能なモノマーとの比率は広範囲で変化することができる。
本発明における水素化は、出発ジエン系ポリマー中に存在する残留二重結合(RDB)の好ましくは少なくとも50%、好ましくは70〜100%、より好ましくは80〜100%、さらにより好ましくは90〜100%、最も好ましくは95〜100%が水素化されることにより理解される。
(実施例1)
水素化反応は、300mLのParr 316ステンレス鋼の反応装置中で実施した。最初に表1で明細を示した25mlのNBRラテックスおよび75mlの水を反応装置に装填した。固体のHG2触媒(0.00487g)を、反応装置の頭部に備え付けた触媒添加デバイスに入れた。反応装置を組み立てた後、NBRラテックスを、室温で20分間、約200psi(1.38MPa)の窒素ガスをバブリングすることにより脱ガスして、次に系を100℃に加熱した。次に、1000psi(6.89MPa)の水素ガスでNBRラテックス中に触媒を添加した。水素圧および反応温度を、反応期間を通じて一定に保った。水素化されたNBRラテックスを、反応装置中に浸したチューブを通して、反応中に間隔をおいてサンプリングした。水素化の結果を表2に示す。4時間後に、水素化率は98%に達する。目に見えるゲルは生じず、生じた水素化されたNBR(「HNBR」)ポリマーを試験すると、メチルエチルケトンに容易に溶解した。HNBRの分子量は249,000であり、PDIは3.1である。分子量変化は水素化のみが原因である。
HG2触媒の代わりにGrubbs II触媒(G2、0.0066g)を使用したことを除いて、同じ反応装置および同じNBRラテックスを比較例laで使用した。水素化率は4時間後15%に達した。水素化期間をさらに10時間に延長すると水素化率は22%という結果になった。水素化率のさらなる増大は達成できなかった。
0.00244gのみのHG2触媒を添加したことを除いて、実施例1で記載した同じ手順を使用した。19時間後に、90%の水素化率が達成され、目に見えるゲルは生じなかった。
反応温度を120℃に上げたことを除いて、実施例1で記載した同じ手順を使用した。1.6時間後に、98%の水素化率が達成され、目に見えるゲルは全く生じなかった。
より高い触媒の装荷(0.00975g)を使用したことを除いて、実施例3で記載した同じ手順を使用した。0.5時間後に、98%の水素化率が達成され、目に見えるゲルは全く生じなかった。
より少量のHG2触媒(0.00125g)を使用したことを除いて、実施例3で記載した同じ手順を使用した。10時間後に、74%の水素化率が達成され、目に見えるゲルは全く生じなかった。
より低い水素圧(500psi; 3.45MPa)を使用したことを除いて、実施例1で記載した同じ手順を使用した。10時間後に、99%の水素化率が達成され、目に見えるゲルは全く生じなかった。
実施例3で記載した同じ手順を使用した。しかしながら、より高い水素圧(1500psi; 10.34MPa)を120℃で使用した。9時間後に、99%の水素化率が達成され、目に見えるゲルは全く生じなかった。
100mlのNBRラテックスおよび0.01253gのHG2触媒を使用した。NBRラテックスを希釈するための増量水は全く加えなかった。全ての他の反応パラメーターは実施例1に記載したのと同じであった。3時間後に、99%の水素化率が達成され、目に見えるゲルは全く生じなかった。
Claims (8)
- 水性懸濁液中に存在するジエン系ポリマーを、一般式(A)
Mはオスミウムまたはルテニウムであり、
X1およびX2は同一であるかまたは異なるアニオン性リガンドであり、
Lは、リガンド、好ましくは無電荷の電子供与体であり、
Yは、酸素(O)、イオウ(S)、N-R1基またはP-R1基であり、ここで、R1は、アルキル、シクロアルキル、アルケニル、アルキニル、アリール、アルコキシ、アルケニルオキシ、アルキニルオキシ、アリールオキシ、アルコキシカルボニル、アルキルアミノ、アルキルチオ、アリールチオ、アルキルスルホニルまたはアルキルスルフィニル基であり、それらは各場合、場合により1つもしくは複数のアルキル、ハロゲン、アルコキシ、アリールまたはヘテロアリール基により置換されていてよく、
R2、R3、R4およびR5は同一であるかまたは異なり、各々水素または有機もしくは無機基であり、ならびに
R6は、水素またはアルキル、アルケニル、アルキニルもしくはアリール基である)
の触媒の存在下で、水素化する工程を含む、水素化されたジエン系ポリマーを調製する方法であって、一般式(A)の触媒が、ジエン系ポリマーの水性懸濁液に固体形態で添加されることを特徴とする方法。 - 前記ジエン系ポリマーが、好ましくは、1,3-ブタジエン、イソプレン、1-メチルブタジエン、2,3-ジメチルブタジエン、ピペリレン、クロロプレン、およびそれらの混合物からなる群から選択される少なくとも1種の(C4〜C6)共役ジエンの反復単位を含有する、請求項1に記載の方法。
- 前記ジエン系ポリマーが、少なくとも1種のさらなる共重合可能なモノマー(b)の反復単位を追加的に含有する、請求項2に記載の方法。
- 前記ジエン系ポリマーが、1,3-ブタジエンとアクリロニトリルのコポリマーである、請求項3に記載の方法。
- 前記水素化が、60℃から200℃、好ましくは80℃から180℃、最も好ましくは100℃から160℃の範囲内の温度で、および0.5MPaから35MPa、より好ましくは3.0MPaから10MPaの範囲内の水素圧で実施される、請求項1から5のいずれか一項に記載の方法。
- 前記一般式(A)の触媒が、水性懸濁液中に存在するジエン系ポリマーの質量に対して0.01から5.0質量%、好ましくは0.02%から2.0質量%の範囲内の量で使用される、請求項1から6のいずれか一項に記載の方法。
- いかなる有機溶媒も存在せずに行われる、請求項1から7のいずれか一項に記載の方法。
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