JP2002212203A - ニトリルコポリマーゴムの水素化 - Google Patents
ニトリルコポリマーゴムの水素化Info
- Publication number
- JP2002212203A JP2002212203A JP2001396245A JP2001396245A JP2002212203A JP 2002212203 A JP2002212203 A JP 2002212203A JP 2001396245 A JP2001396245 A JP 2001396245A JP 2001396245 A JP2001396245 A JP 2001396245A JP 2002212203 A JP2002212203 A JP 2002212203A
- Authority
- JP
- Japan
- Prior art keywords
- hydrogenation
- copolymer
- epoxidized
- cocatalyst
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 73
- 229920001577 copolymer Polymers 0.000 title claims abstract description 66
- 229920001971 elastomer Polymers 0.000 title claims abstract description 16
- 239000005060 rubber Substances 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 54
- 239000003054 catalyst Substances 0.000 claims abstract description 33
- 150000004696 coordination complex Chemical class 0.000 claims abstract description 9
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 31
- 239000000370 acceptor Substances 0.000 description 29
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 150000002118 epoxides Chemical group 0.000 description 10
- 229910052703 rhodium Inorganic materials 0.000 description 10
- 239000010948 rhodium Substances 0.000 description 10
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 9
- 239000003446 ligand Substances 0.000 description 9
- 150000001993 dienes Chemical class 0.000 description 8
- 229920013648 Perbunan Polymers 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- 238000004566 IR spectroscopy Methods 0.000 description 6
- 229920013647 Krynac Polymers 0.000 description 6
- 229920000459 Nitrile rubber Polymers 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 239000003549 soybean oil Substances 0.000 description 5
- 235000012424 soybean oil Nutrition 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 4
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241001441571 Hiodontidae Species 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- -1 vinyl compound Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 235000019483 Peanut oil Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910052785 arsenic Inorganic materials 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- IETKMTGYQIVLRF-UHFFFAOYSA-N carbon monoxide;rhodium;triphenylphosphane Chemical compound [Rh].[O+]#[C-].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 IETKMTGYQIVLRF-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003426 co-catalyst Substances 0.000 description 3
- 239000002285 corn oil Substances 0.000 description 3
- 235000005687 corn oil Nutrition 0.000 description 3
- 235000012343 cottonseed oil Nutrition 0.000 description 3
- 239000002385 cottonseed oil Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000000944 linseed oil Substances 0.000 description 3
- 235000021388 linseed oil Nutrition 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000004006 olive oil Substances 0.000 description 3
- 235000008390 olive oil Nutrition 0.000 description 3
- 239000000312 peanut oil Substances 0.000 description 3
- 239000002383 tung oil Substances 0.000 description 3
- 150000007934 α,β-unsaturated carboxylic acids Chemical group 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 235000019482 Palm oil Nutrition 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229910021604 Rhodium(III) chloride Inorganic materials 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000010793 Steam injection (oil industry) Methods 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 235000014121 butter Nutrition 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 239000003026 cod liver oil Substances 0.000 description 2
- 235000012716 cod liver oil Nutrition 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- 239000003346 palm kernel oil Substances 0.000 description 2
- 235000019865 palm kernel oil Nutrition 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 229910052702 rhenium Inorganic materials 0.000 description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 2
- FCQRKDSALKMOGU-UHFFFAOYSA-K rhodium(3+);triphenylphosphane;trichloride Chemical compound Cl[Rh](Cl)Cl.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 FCQRKDSALKMOGU-UHFFFAOYSA-K 0.000 description 2
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
- RGVUOOXMJUYRPP-UHFFFAOYSA-N (2,3-dimethylphenyl)-diphenylphosphane Chemical compound CC1=CC=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1C RGVUOOXMJUYRPP-UHFFFAOYSA-N 0.000 description 1
- KYLUAQBYONVMCP-UHFFFAOYSA-N (2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P KYLUAQBYONVMCP-UHFFFAOYSA-N 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- 238000011925 1,2-addition Methods 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- KCVSMGBGFUGLMU-UHFFFAOYSA-N 2-cyclopenta-2,4-dien-1-ylethyl-(2-diphenylphosphanylethyl)-phenylphosphane Chemical compound C(CP(CCP(c1ccccc1)c1ccccc1)c1ccccc1)C1C=CC=C1 KCVSMGBGFUGLMU-UHFFFAOYSA-N 0.000 description 1
- MICCAWHGLAEEEX-UHFFFAOYSA-N 2-cyclopenta-2,4-dien-1-ylethyl-(3-diphenylphosphanylpropyl)-phenylphosphane Chemical compound C(CP(CCC1C=CC=C1)c1ccccc1)CP(c1ccccc1)c1ccccc1 MICCAWHGLAEEEX-UHFFFAOYSA-N 0.000 description 1
- PTFVEGSFABPRIA-UHFFFAOYSA-N 2-cyclopenta-2,4-dien-1-ylethyl-(4-diphenylphosphanylbutyl)-phenylphosphane Chemical compound C(CCP(c1ccccc1)c1ccccc1)CP(CCC1C=CC=C1)c1ccccc1 PTFVEGSFABPRIA-UHFFFAOYSA-N 0.000 description 1
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- YGRVCNYIEKLRED-UHFFFAOYSA-N 4,4-diphenylbutylphosphane Chemical compound C=1C=CC=CC=1C(CCCP)C1=CC=CC=C1 YGRVCNYIEKLRED-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- SFUCQIUDZBXOOP-UHFFFAOYSA-N 4-bis(4-cyanophenyl)phosphanylbenzonitrile Chemical compound C1=CC(C#N)=CC=C1P(C=1C=CC(=CC=1)C#N)C1=CC=C(C#N)C=C1 SFUCQIUDZBXOOP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XVVRJVYAGSGYIB-UHFFFAOYSA-N [2,3,4-tris(2,3-dimethylphenyl)phenyl]phosphane Chemical compound CC1=CC=CC(C=2C(=C(C=3C(=C(C)C=CC=3)C)C(P)=CC=2)C=2C(=C(C)C=CC=2)C)=C1C XVVRJVYAGSGYIB-UHFFFAOYSA-N 0.000 description 1
- LYEZAEXHLSEXON-UHFFFAOYSA-N [RhH3].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [RhH3].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 LYEZAEXHLSEXON-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000003679 aging effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001450 anions Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- DGJOCBJPCSLLKK-UHFFFAOYSA-N bis(2,3-dimethoxyphenyl)-phenylphosphane Chemical compound COC1=CC=CC(P(C=2C=CC=CC=2)C=2C(=C(OC)C=CC=2)OC)=C1OC DGJOCBJPCSLLKK-UHFFFAOYSA-N 0.000 description 1
- FOZRTQVZEZIVAK-UHFFFAOYSA-N bis(2,3-dimethylphenyl)-phenylphosphane Chemical compound CC1=CC=CC(P(C=2C=CC=CC=2)C=2C(=C(C)C=CC=2)C)=C1C FOZRTQVZEZIVAK-UHFFFAOYSA-N 0.000 description 1
- 229940006460 bromide ion Drugs 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- IQIRNRBHGWXSLV-UHFFFAOYSA-N cyclohexyl(diphenyl)arsane Chemical compound C1CCCCC1[As](C=1C=CC=CC=1)C1=CC=CC=C1 IQIRNRBHGWXSLV-UHFFFAOYSA-N 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- BOHNWWTZVYEMMA-UHFFFAOYSA-N dibutyl(phenyl)arsane Chemical compound CCCC[As](CCCC)C1=CC=CC=C1 BOHNWWTZVYEMMA-UHFFFAOYSA-N 0.000 description 1
- MUBZDQFQOYOFBM-UHFFFAOYSA-N diethyl(phenyl)arsane Chemical compound CC[As](CC)C1=CC=CC=C1 MUBZDQFQOYOFBM-UHFFFAOYSA-N 0.000 description 1
- LVTCZSBUROAWTE-UHFFFAOYSA-N diethyl(phenyl)phosphane Chemical compound CCP(CC)C1=CC=CC=C1 LVTCZSBUROAWTE-UHFFFAOYSA-N 0.000 description 1
- VPHDWBWBTVPDAZ-UHFFFAOYSA-N diphenyl-(2,3,4-trimethoxyphenyl)phosphane Chemical compound COC1=C(OC)C(OC)=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 VPHDWBWBTVPDAZ-UHFFFAOYSA-N 0.000 description 1
- PFLORXVMVNHPEC-UHFFFAOYSA-N diphenyl-(2,3,4-trimethylphenyl)phosphane Chemical compound CC1=C(C)C(C)=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 PFLORXVMVNHPEC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- DLINORNFHVEIFE-UHFFFAOYSA-N hydrogen peroxide;zinc Chemical compound [Zn].OO DLINORNFHVEIFE-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002736 metal compounds Chemical group 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- ZJAKNSASNSLIOG-UHFFFAOYSA-N methyl 4-bis(4-methoxycarbonylphenyl)phosphanylbenzoate Chemical compound C1=CC(C(=O)OC)=CC=C1P(C=1C=CC(=CC=1)C(=O)OC)C1=CC=C(C(=O)OC)C=C1 ZJAKNSASNSLIOG-UHFFFAOYSA-N 0.000 description 1
- UJNZOIKQAUQOCN-UHFFFAOYSA-N methyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C)C1=CC=CC=C1 UJNZOIKQAUQOCN-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- VWSSOSUSCXKKKL-UHFFFAOYSA-N phenyl-bis(2,3,4-trimethoxyphenyl)phosphane Chemical compound COC1=C(OC)C(OC)=CC=C1P(C=1C(=C(OC)C(OC)=CC=1)OC)C1=CC=CC=C1 VWSSOSUSCXKKKL-UHFFFAOYSA-N 0.000 description 1
- OHUBTNCFAYBUKT-UHFFFAOYSA-N phenyl-bis(2,3,4-trimethylphenyl)phosphane Chemical compound CC1=C(C)C(C)=CC=C1P(C=1C(=C(C)C(C)=CC=1)C)C1=CC=CC=C1 OHUBTNCFAYBUKT-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- QQZMDXUEROTLLD-UHFFFAOYSA-N rhodium;triphenylphosphane Chemical compound [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 QQZMDXUEROTLLD-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
- 125000003203 triacylglycerol group Chemical group 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical group C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- DMEUUKUNSVFYAA-UHFFFAOYSA-N trinaphthalen-1-ylphosphane Chemical compound C1=CC=C2C(P(C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 DMEUUKUNSVFYAA-UHFFFAOYSA-N 0.000 description 1
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
- JRIXTOAARDBEIG-UHFFFAOYSA-N tris(2,3,4-trimethoxyphenyl)phosphane Chemical compound COC1=C(OC)C(OC)=CC=C1P(C=1C(=C(OC)C(OC)=CC=1)OC)C1=CC=C(OC)C(OC)=C1OC JRIXTOAARDBEIG-UHFFFAOYSA-N 0.000 description 1
- PADOFXALCIVUFS-UHFFFAOYSA-N tris(2,3-dimethoxyphenyl)phosphane Chemical compound COC1=CC=CC(P(C=2C(=C(OC)C=CC=2)OC)C=2C(=C(OC)C=CC=2)OC)=C1OC PADOFXALCIVUFS-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229940105296 zinc peroxide Drugs 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2329844 | 2000-12-28 | ||
| CA002329844A CA2329844A1 (en) | 2000-12-28 | 2000-12-28 | Esbo enhanced hydrogenation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002212203A true JP2002212203A (ja) | 2002-07-31 |
| JP2002212203A5 JP2002212203A5 (enExample) | 2005-07-21 |
Family
ID=4168007
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001396245A Pending JP2002212203A (ja) | 2000-12-28 | 2001-12-27 | ニトリルコポリマーゴムの水素化 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6683136B2 (enExample) |
| EP (1) | EP1219640A3 (enExample) |
| JP (1) | JP2002212203A (enExample) |
| CA (1) | CA2329844A1 (enExample) |
| MX (1) | MXPA01012875A (enExample) |
Families Citing this family (70)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1757623A1 (en) * | 2005-07-14 | 2007-02-28 | Lanxess Inc. | Process for the preparation of low mooney nitrile terpolymers |
| ATE538139T1 (de) * | 2005-08-30 | 2012-01-15 | Lanxess Deutschland Gmbh | Verwendung von katalysatoren für den metatheseabbau von nitrilkautschuk |
| DE102005042265A1 (de) | 2005-09-06 | 2007-03-08 | Lanxess Deutschland Gmbh | Vernetzbare Zusammensetzungen, daraus erhältliche thermoplastische Elastomere und deren Verwendung |
| DE102005047115A1 (de) * | 2005-09-30 | 2007-04-05 | Lanxess Deutschland Gmbh | Vernetzbare Zusammensetzungen, Verfahren zu deren Herstellung und deren Verwendung |
| DE102005059625A1 (de) * | 2005-12-14 | 2007-06-21 | Lanxess Deutschland Gmbh | Mikrogel-enthaltende vulkanisierbare Zusammensetzung auf Basis von hydriertem Nitrilkautschuk |
| DE102005061628A1 (de) * | 2005-12-21 | 2007-06-28 | Lanxess Deutschland Gmbh | Hydrierter Nitrilkautschuk mit enger Molekulargewichtsverteilung, ein Verfahren zu seiner Herstellung und seine Verwendung |
| DE102005061627A1 (de) * | 2005-12-21 | 2007-06-28 | Lanxess Deutschland Gmbh | Synthetischer Kautschuk mit enger Molekulargewichtsverteilung, ein Verfahren zu seiner Herstellung und seine Verwendung |
| DE102006008520A1 (de) * | 2006-02-22 | 2007-08-23 | Lanxess Deutschland Gmbh | Neue Katalysator-Systeme und deren Verwendung für Metathese-Reaktionen |
| DE102006008521A1 (de) * | 2006-02-22 | 2007-08-23 | Lanxess Deutschland Gmbh | Verwendung von Katalysatoren mit erhöhter Aktivität für die NBR-Metathese |
| DE102006040569A1 (de) * | 2006-08-30 | 2008-03-06 | Lanxess Deutschland Gmbh | Verfahren zum Metathese-Abbau von Nitrilkautschuken |
| DE102007024010A1 (de) * | 2007-05-22 | 2008-11-27 | Lanxess Deutschland Gmbh | Nitrilkautschuke |
| DE102007024008A1 (de) * | 2007-05-22 | 2008-11-27 | Lanxess Deutschland Gmbh | Nitrilkautschuke |
| DE102007024011A1 (de) * | 2007-05-22 | 2008-11-27 | Lanxess Deutschland Gmbh | Nitrilkautschuke |
| DE102007039526A1 (de) * | 2007-08-21 | 2009-02-26 | Lanxess Deutschland Gmbh | Katalysator-Systeme und deren Verwendung für Metathese-Reaktionen |
| DE102007039695A1 (de) | 2007-08-22 | 2009-02-26 | Lanxess Deutschland Gmbh | Katalysatoren für Metathese-Reaktionen |
| EP2027920B1 (de) | 2007-08-21 | 2014-10-08 | LANXESS Deutschland GmbH | Katalysatoren für Metathese-Reaktionen |
| DE102007039527A1 (de) | 2007-08-21 | 2009-02-26 | Lanxess Deutschland Gmbh | Katalysatoren für Metathese-Reaktionen |
| EP2028194B1 (en) | 2007-08-21 | 2010-05-12 | Lanxess Deutschland GmbH | Metathesis of nitrile rubbers in the presence of transition metal complex catalysts |
| DE102007039525A1 (de) | 2007-08-21 | 2009-02-26 | Lanxess Deutschland Gmbh | Verfahren zum Metathese-Abbau von Nitrilkautschuk |
| EP2072536A1 (en) | 2007-12-17 | 2009-06-24 | Lanxess Inc. | Hydrogenation of diene-based polymers |
| EP2075262A1 (en) | 2007-12-17 | 2009-07-01 | Lanxess Inc. | Hydrogenation of diene-based polymers |
| EP2238175B1 (de) * | 2008-01-29 | 2011-12-14 | LANXESS Deutschland GmbH | Optional alkylthio-endgruppen enthaltende optional hydrierte nitrilkautschuke |
| RU2464278C9 (ru) * | 2008-01-29 | 2013-04-27 | ЛЕНКСЕСС Дойчланд ГмбХ | При необходимости гидрированные нитрильные каучуки, содержащие при необходимости концевые алкилтиогруппы |
| KR101233846B1 (ko) * | 2008-01-29 | 2013-02-18 | 란세스 도이치란트 게엠베하 | 알킬티오 말단기를 임의로 함유하고 임의로 수소화된 니트릴 고무 |
| EP2147721A1 (de) * | 2008-07-08 | 2010-01-27 | Lanxess Deutschland GmbH | Katalysator-Systeme und deren Verwendung für Metathese-Reaktionen |
| EP2143489A1 (de) * | 2008-07-08 | 2010-01-13 | Lanxess Deutschland GmbH | Katalysator-Systeme und deren Verwendung für Metathese-Reaktionen |
| EP2267037B1 (de) | 2009-06-26 | 2012-11-14 | LANXESS Deutschland GmbH | Verwendung von ganz oder teilweise hydrierten Nitrilkautschuken |
| EP2289622A1 (en) | 2009-08-31 | 2011-03-02 | LANXESS Deutschland GmbH | Ruthenium based catalysts for the metathesis of nitrile rubbers |
| WO2011023771A1 (en) | 2009-08-31 | 2011-03-03 | Lanxess Deutschland Gmbh | Vulcanizable polymer composition comprising a low molecular weight optionally hydrogenated nitrile rubber |
| EP2289623A1 (en) | 2009-08-31 | 2011-03-02 | LANXESS Deutschland GmbH | Metathesis of nitrile rubbers in the presence of transition metal catalysts |
| EP2385074A1 (de) | 2010-05-07 | 2011-11-09 | LANXESS Deutschland GmbH | Nitrilkautschuke und deren Herstellung in organischen Lösungsmitteln |
| EP2298824A1 (de) | 2009-09-17 | 2011-03-23 | LANXESS Deutschland GmbH | Nitrilkautschuke und deren Herstellung in organischen Lösungsmitteln |
| IN2012DN02284A (enExample) | 2009-09-17 | 2015-08-21 | Lanxess Deutschland Gmbh | |
| EP2316861A1 (de) | 2009-11-03 | 2011-05-04 | LANXESS Deutschland GmbH | Nitrilkautschuke |
| EP2368917B1 (en) | 2010-03-25 | 2013-01-09 | LANXESS International SA | Process for the production of water and solvent-free hydrogenated nitrile rubbers |
| EP2386600B1 (de) | 2010-04-15 | 2013-06-19 | LANXESS Deutschland GmbH | Isocyanatgruppen-enthaltende Vernetzer für Nitrilkautschuke |
| EP2418225A1 (de) | 2010-08-09 | 2012-02-15 | LANXESS Deutschland GmbH | Teilhydrierte Nitrilkautschuke |
| EP2423235A1 (de) | 2010-08-31 | 2012-02-29 | LANXESS Deutschland GmbH | Verfahren zur Herstellung von Nitrilkautschuken in organischen Lösungsmitteln |
| EP2423238A1 (de) | 2010-08-31 | 2012-02-29 | LANXESS Deutschland GmbH | Verfahren zur Herstellung von Nitrilkautschuken in organischen Lösungsmitteln |
| EP2423234A1 (de) | 2010-08-31 | 2012-02-29 | LANXESS Deutschland GmbH | Kautschukblends aus verschiedenen Nitrilkautschuken |
| EP2471852A1 (de) | 2010-12-29 | 2012-07-04 | Lanxess Deutschland GmbH | Vulkanisierbare Zusammensetzungen auf Basis Epoxygruppen-haltiger Nitrilkautschuke |
| EP2471851A1 (de) | 2010-12-29 | 2012-07-04 | LANXESS Deutschland GmbH | Vulkanisierbare Zusammensetzungen auf Basis Epoxygruppen-haltiger Nitrilkautschuke |
| EP2484700B1 (de) | 2011-02-04 | 2013-10-09 | LANXESS Deutschland GmbH | Funktionalisierte Nitrilkautschuke und ihre Herstellung |
| WO2012174734A1 (en) | 2011-06-24 | 2012-12-27 | Lanxess Deutschland Gmbh | Solution polymerization/co-polymerization of dienes, hydrogenation of dienerubbers and hydrogenated dienerubbers |
| EP2554558A1 (de) | 2011-08-02 | 2013-02-06 | Lanxess Deutschland GmbH | Verfahren zur Herstellung von Nitrilkautschuken in organischen Lösungsmitteln |
| EP2565229A1 (de) | 2011-09-02 | 2013-03-06 | LANXESS Deutschland GmbH | Vulkanisierbare Zusammensetzungen auf Basis von Epoxygruppen-haltigen Ethylenvinylacetat-Copolymerisaten |
| EP2581407A1 (de) | 2011-10-11 | 2013-04-17 | Lanxess Deutschland GmbH | Vulkanisierbare Zusammensetzungen auf Basis Epoxygruppen-haltiger Nitrilkautschuke |
| EP2581409A1 (de) | 2011-10-11 | 2013-04-17 | Lanxess Deutschland GmbH | Vulkanisierbare Zusammensetzungen auf Basis Epoxygruppen-haltiger Nitrilkautschuke |
| WO2013098052A2 (en) | 2011-12-28 | 2013-07-04 | Lanxess Deutschland Gmbh | Metathesis of nitrile rubbers in the presence of transition metal complex catalysts |
| KR102365309B1 (ko) | 2014-02-03 | 2022-02-22 | 아란세오 도이치란드 게엠베하 | 안정화된 고무 |
| CN104338558B (zh) * | 2014-09-11 | 2017-04-05 | 华南理工大学 | 杂化树状聚合物负载双金属纳米粒子催化剂及其制备方法与应用 |
| CN105622783B (zh) * | 2014-10-29 | 2017-06-30 | 中国石油化工股份有限公司 | 一种共聚物的制备方法 |
| EP3034518B1 (de) | 2014-12-19 | 2017-05-24 | ARLANXEO Deutschland GmbH | Farbstabile Nitrilkautschuke |
| EP3196239A1 (de) | 2016-01-25 | 2017-07-26 | ARLANXEO Deutschland GmbH | Vulkanisierbare zusammensetzungen auf basis von hydriertem nitrilkautschuk, verfahren zu deren herstellung und deren verwendung |
| EP3248989B1 (en) | 2016-05-23 | 2020-12-02 | University Of Waterloo | Hydrogenation of nitrile groups in hydrogenated nitrile butadiene rubber and tandem hydrogenation of nitrile groups and olefinic groups in nitrile butadiene rubber using a ruthenium or rhodium complex and a basic reagent |
| EP3248988B1 (en) | 2016-05-23 | 2020-12-02 | University Of Waterloo | Hydrogenation of nitrile groups in hydrogenated nitrile butadiene rubber and tandem hydrogenation of nitrile groups and olefinic groups in nitrile butadiene rubber using an unsupported rhodium containing catalyst |
| EP3255088B1 (de) | 2016-06-07 | 2020-04-29 | ARLANXEO Deutschland GmbH | Verwendung von vulkanisierbaren zusammensetzungen und vulkanisaten in kontakt mit kühlmittel enthaltend silan-beschichteten wollastonit |
| CN106179504B (zh) * | 2016-07-11 | 2018-10-09 | 华南理工大学 | 杂化树状聚合物负载金属催化剂及其制备方法与应用 |
| CN106512993B (zh) * | 2016-08-30 | 2018-11-16 | 北京化工大学 | 钯-钌双金属纳米催化剂制备及加氢应用 |
| CN106423283B (zh) * | 2016-08-31 | 2019-05-17 | 北京化工大学 | 二元胺过渡金属络合物催化剂及其制备方法与应用 |
| CN111032764A (zh) | 2017-08-16 | 2020-04-17 | 阿朗新科德国有限责任公司 | 包含氢化丁腈橡胶的可固化的组合物、由其生产的固化橡胶以及其用途 |
| CN111107985B (zh) | 2017-09-20 | 2022-06-07 | 阿朗新科德国有限责任公司 | 具有高热导率的可固化的hnbr组合物 |
| JP7248677B2 (ja) | 2017-12-08 | 2023-03-29 | アランセオ・ドイチュランド・ゲーエムベーハー | ルテニウム錯体触媒を使用してニトリルゴムを製造するためのプロセス |
| EP3781309A1 (en) | 2018-04-20 | 2021-02-24 | ARLANXEO Deutschland GmbH | Hydrogenation catalyst compositions and their use for hydrogenation of nitrile rubber |
| CN112088044B (zh) | 2018-04-27 | 2023-10-24 | 阿朗新科德国有限责任公司 | 钌和锇催化剂用于丁腈橡胶复分解的用途 |
| JP2021532208A (ja) | 2018-07-23 | 2021-11-25 | アランセオ・ドイチュランド・ゲーエムベーハー | 水素化ニトリルゴムを製造するための方法及びそのｈｎｂｒ組成物 |
| WO2020020629A1 (en) | 2018-07-23 | 2020-01-30 | Arlanxeo Deutschland Gmbh | Use of catalysts for the metathesis of nitrile rubber |
| CN113164941B (zh) | 2018-12-12 | 2023-12-12 | 阿朗新科德国有限责任公司 | 含复分解催化剂和至少一种酚类化合物的催化剂体系及使用催化剂体系进行丁腈橡胶(nbr)的复分解的方法 |
| WO2020126345A1 (en) | 2018-12-17 | 2020-06-25 | Arlanxeo Deutschland Gmbh | Process for preparing hnbr solutions with alternative solvents |
| WO2020126343A1 (en) | 2018-12-19 | 2020-06-25 | Arlanxeo Deutschland Gmbh | Electrode composition for a cathode of a cell of a lithium-ion battery, a cathode slurry composition, a cathode and the battery incorporating it |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE654989C (de) | 1930-05-06 | 1938-01-06 | Ig Farbenindustrie Ag | Verfahren zur Herstellung von Polymerisationsprodukten |
| US3700637A (en) | 1970-05-08 | 1972-10-24 | Shell Oil Co | Diene-nitrile rubbers |
| US3673281A (en) * | 1971-01-29 | 1972-06-27 | Basf Ag | Catalytic hydrogenation of polymers containing double bonds |
| DE2539132C2 (de) * | 1975-09-03 | 1987-04-09 | Bayer Ag, 5090 Leverkusen | Verwendung hydrierter Dien-Copolymere als temperaturbeständige Materialien auf dem Dichtungssektor |
| CA1220300A (en) * | 1982-12-08 | 1987-04-07 | Polysar Limited | Polymer hydrogenation process |
| DE3433075A1 (de) * | 1984-09-08 | 1986-03-20 | Bayer Ag, 5090 Leverkusen | Niedermolekulare copolymerisate und daraus hergestellte covulkanisate |
| DE3433392A1 (de) * | 1984-09-12 | 1986-03-20 | Bayer Ag, 5090 Leverkusen | Hydrierung nitrilgruppenhaltiger ungesaettigter polymerer |
| US5075388A (en) * | 1990-12-13 | 1991-12-24 | Rempel Garry L | Amine modified hydrogenation of nitrile rubber |
| NL1004993C2 (nl) * | 1997-01-14 | 1998-07-15 | Dsm Nv | Werkwijze voor de bereiding van RuHX(H2)(PR3)2 en de toepassing hiervan als hydrogeneringskatalysator. |
| CA2329551A1 (en) * | 2000-12-22 | 2002-06-22 | Bayer Inc. | Process for the production of hydrogenated nitrile rubber |
-
2000
- 2000-12-28 CA CA002329844A patent/CA2329844A1/en not_active Abandoned
-
2001
- 2001-12-13 MX MXPA01012875A patent/MXPA01012875A/es not_active Application Discontinuation
- 2001-12-17 EP EP01129343A patent/EP1219640A3/en not_active Withdrawn
- 2001-12-19 US US10/027,762 patent/US6683136B2/en not_active Expired - Fee Related
- 2001-12-27 JP JP2001396245A patent/JP2002212203A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP1219640A3 (en) | 2002-11-13 |
| CA2329844A1 (en) | 2002-06-28 |
| MXPA01012875A (es) | 2002-07-09 |
| US20020128393A1 (en) | 2002-09-12 |
| EP1219640A2 (en) | 2002-07-03 |
| US6683136B2 (en) | 2004-01-27 |
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