JPH0237211B2 - - Google Patents
Info
- Publication number
- JPH0237211B2 JPH0237211B2 JP57005852A JP585282A JPH0237211B2 JP H0237211 B2 JPH0237211 B2 JP H0237211B2 JP 57005852 A JP57005852 A JP 57005852A JP 585282 A JP585282 A JP 585282A JP H0237211 B2 JPH0237211 B2 JP H0237211B2
- Authority
- JP
- Japan
- Prior art keywords
- platinum
- styrene
- compounds
- reaction
- unsaturated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 80
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 48
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 26
- -1 platinum halide Chemical class 0.000 claims abstract description 20
- 150000002367 halogens Chemical class 0.000 claims abstract description 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 14
- 150000003440 styrenes Chemical class 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims description 27
- 125000004429 atom Chemical group 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 150000003057 platinum Chemical class 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 6
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 32
- 150000003961 organosilicon compounds Chemical class 0.000 abstract description 17
- BUJVWPBYOKNVRO-UHFFFAOYSA-N platinum;styrene Chemical class [Pt].C=CC1=CC=CC=C1 BUJVWPBYOKNVRO-UHFFFAOYSA-N 0.000 abstract description 14
- 125000001931 aliphatic group Chemical group 0.000 abstract description 9
- 239000000463 material Substances 0.000 abstract description 6
- 239000000203 mixture Substances 0.000 description 32
- 229920001296 polysiloxane Polymers 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 150000002894 organic compounds Chemical class 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 238000007259 addition reaction Methods 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 150000003377 silicon compounds Chemical class 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 150000003058 platinum compounds Chemical class 0.000 description 3
- 238000004382 potting Methods 0.000 description 3
- 239000010453 quartz Substances 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- SJNALLRHIVGIBI-UHFFFAOYSA-N allyl cyanide Chemical group C=CCC#N SJNALLRHIVGIBI-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910021485 fumed silica Inorganic materials 0.000 description 2
- 150000004687 hexahydrates Chemical class 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- OBRYRJYZWVLVLF-UHFFFAOYSA-N 1-ethenyl-4-ethoxybenzene Chemical compound CCOC1=CC=C(C=C)C=C1 OBRYRJYZWVLVLF-UHFFFAOYSA-N 0.000 description 1
- WHFHDVDXYKOSKI-UHFFFAOYSA-N 1-ethenyl-4-ethylbenzene Chemical compound CCC1=CC=C(C=C)C=C1 WHFHDVDXYKOSKI-UHFFFAOYSA-N 0.000 description 1
- KUIZKZHDMPERHR-UHFFFAOYSA-N 1-phenylprop-2-en-1-one Chemical compound C=CC(=O)C1=CC=CC=C1 KUIZKZHDMPERHR-UHFFFAOYSA-N 0.000 description 1
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 description 1
- QIJQUSMHFFKBLU-UHFFFAOYSA-N 3-[dichloro(ethenyl)silyl]propanenitrile Chemical compound C=C[Si](Cl)(Cl)CCC#N QIJQUSMHFFKBLU-UHFFFAOYSA-N 0.000 description 1
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000005047 Allyltrichlorosilane Substances 0.000 description 1
- 229910004723 HSiO1.5 Inorganic materials 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-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
- 229910008072 Si-N-Si Inorganic materials 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000004964 aerogel Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 description 1
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- SOYVLBDERBHIME-UHFFFAOYSA-N chloro(diethyl)silicon Chemical compound CC[Si](Cl)CC SOYVLBDERBHIME-UHFFFAOYSA-N 0.000 description 1
- YCITZMJNBYYMJO-UHFFFAOYSA-N chloro(diphenyl)silicon Chemical compound C=1C=CC=CC=1[Si](Cl)C1=CC=CC=C1 YCITZMJNBYYMJO-UHFFFAOYSA-N 0.000 description 1
- ZIFXYFOVERKZLG-UHFFFAOYSA-N chloro-methyl-(2-phenylethenyl)silane Chemical compound C[SiH](Cl)C=CC1=CC=CC=C1 ZIFXYFOVERKZLG-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 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
- QRBVERKDYUOGHB-UHFFFAOYSA-L cyclopropane;dichloroplatinum Chemical compound C1CC1.Cl[Pt]Cl QRBVERKDYUOGHB-UHFFFAOYSA-L 0.000 description 1
- 239000002978 dental impression material Substances 0.000 description 1
- VJIYRPVGAZXYBD-UHFFFAOYSA-N dibromosilane Chemical compound Br[SiH2]Br VJIYRPVGAZXYBD-UHFFFAOYSA-N 0.000 description 1
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 description 1
- XNAFLNBULDHNJS-UHFFFAOYSA-N dichloro(phenyl)silicon Chemical compound Cl[Si](Cl)C1=CC=CC=C1 XNAFLNBULDHNJS-UHFFFAOYSA-N 0.000 description 1
- VTEHVUWHCBXMPI-UHFFFAOYSA-N dichloro-bis(prop-2-enyl)silane Chemical compound C=CC[Si](Cl)(Cl)CC=C VTEHVUWHCBXMPI-UHFFFAOYSA-N 0.000 description 1
- YLJJAVFOBDSYAN-UHFFFAOYSA-N dichloro-ethenyl-methylsilane Chemical compound C[Si](Cl)(Cl)C=C YLJJAVFOBDSYAN-UHFFFAOYSA-N 0.000 description 1
- QDASGLPLQWLMSJ-UHFFFAOYSA-N dichloro-ethenyl-phenylsilane Chemical compound C=C[Si](Cl)(Cl)C1=CC=CC=C1 QDASGLPLQWLMSJ-UHFFFAOYSA-N 0.000 description 1
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- MYRTYDVEIRVNKP-UHFFFAOYSA-N divinylbenzene Substances C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- BITPLIXHRASDQB-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)C=C BITPLIXHRASDQB-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940052303 ethers for general anesthesia Drugs 0.000 description 1
- DRUOQOFQRYFQGB-UHFFFAOYSA-N ethoxy(dimethyl)silicon Chemical compound CCO[Si](C)C DRUOQOFQRYFQGB-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000003106 haloaryl group Chemical group 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000007774 longterm Effects 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
- 229910052751 metal Chemical class 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 239000005048 methyldichlorosilane Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- RPMXALUWKZHYOV-UHFFFAOYSA-N nitroethene Chemical group [O-][N+](=O)C=C RPMXALUWKZHYOV-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000005474 octanoate group Chemical group 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- IMYGMRDBUAOCFV-UHFFFAOYSA-N trichloro(dichlorosilyloxy)silane Chemical compound Cl[SiH](Cl)O[Si](Cl)(Cl)Cl IMYGMRDBUAOCFV-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- HKFSBKQQYCMCKO-UHFFFAOYSA-N trichloro(prop-2-enyl)silane Chemical compound Cl[Si](Cl)(Cl)CC=C HKFSBKQQYCMCKO-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2291—Olefins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
- A61K6/61—Cationic, anionic or redox initiators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/90—Compositions for taking dental impressions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0801—General processes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/828—Platinum
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
- B01J31/30—Halides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/230,462 US4394317A (en) | 1981-02-02 | 1981-02-02 | Platinum-styrene complexes which promote hydrosilation reactions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57136945A JPS57136945A (en) | 1982-08-24 |
| JPH0237211B2 true JPH0237211B2 (en, 2012) | 1990-08-23 |
Family
ID=22865319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57005852A Granted JPS57136945A (en) | 1981-02-02 | 1982-01-18 | Platinum-styrene complex for promoting hydrosilinating reaction |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US4394317A (en, 2012) |
| EP (1) | EP0057459B1 (en, 2012) |
| JP (1) | JPS57136945A (en, 2012) |
| AT (1) | ATE11543T1 (en, 2012) |
| AU (1) | AU540319B2 (en, 2012) |
| BR (1) | BR8200450A (en, 2012) |
| CA (1) | CA1180319A (en, 2012) |
| DE (1) | DE3262070D1 (en, 2012) |
Families Citing this family (131)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4593084A (en) * | 1984-11-19 | 1986-06-03 | Doe Corning Corporation | Platinum-phosphine-vinylsiloxane complexes |
| FR2575085B1 (fr) * | 1984-12-20 | 1987-02-20 | Rhone Poulenc Spec Chim | Complexe platine-triene comme catalyseur de reaction d'hydrosilylation et son procede de preparation |
| FR2575086B1 (fr) * | 1984-12-20 | 1987-02-20 | Rhone Poulenc Spec Chim | Complexe platine-alcenylcyclohexene comme catalyseur de reaction d'hydrosilylation et son procede de preparation |
| US4681963A (en) * | 1985-12-19 | 1987-07-21 | General Electric Company | Hydrosilylation catalyst, method for making and use |
| JPS63198692A (ja) * | 1987-02-13 | 1988-08-17 | Shin Etsu Chem Co Ltd | シクロアルキルシランの製造方法 |
| JPH089006B2 (ja) * | 1989-11-15 | 1996-01-31 | 信越化学工業株式会社 | 白金触媒組成物及びその製造方法 |
| US4965386A (en) * | 1990-03-26 | 1990-10-23 | E. I. Du Pont De Nemours And Company | Hydrosilation, and dehydrocondensation of silicon hydrides, catalyzed by scandium, yttrium and rare earth metal compounds |
| US5328974A (en) * | 1993-05-06 | 1994-07-12 | Wacker Silicones Corporation | Platinum catalyst and a curable organopolysiloxane composition containing said platinum catalyst |
| FR2727115B1 (fr) | 1994-11-17 | 1996-12-27 | Oreal | Nouveaux filtres solaires, compositions cosmetiques photoprotectrices les contenant et utilisations |
| FR2727114B1 (fr) | 1994-11-17 | 1996-12-27 | Oreal | Nouveaux filtres solaires, compositions cosmetiques photoprotectrices les contenant et utilisations |
| FR2727113B1 (fr) | 1994-11-17 | 1996-12-27 | Oreal | Nouveaux filtres solaires, compositions cosmetiques photoprotectrices les contenant et utilisations |
| FR2740479B1 (fr) | 1995-10-31 | 1998-01-09 | Rhone Poulenc Chimie | Utilisation d'une composition organopolysiloxanique pour l'enduction d'une bande transporteuse et bande transporteuse ainsi obtenue |
| FR2743564A1 (fr) | 1996-01-11 | 1997-07-18 | Michelin & Cie | Compositions de caoutchouc pour enveloppes de pneumatiques a base de silices contenant un additif de renforcement a base d'un polyorganosiloxane fonctionnalise et d'un compose organosilane . |
| US5567848A (en) * | 1996-01-16 | 1996-10-22 | Dow Corning Corporation | Alkyne hydrosilation using cycloalkadiene-platinum complex as catalyst |
| DE19634971A1 (de) * | 1996-08-29 | 1998-03-05 | Wacker Chemie Gmbh | Flüssigsiliconkautschuk mit verbessertem Druckverformungsrest |
| DE19808117A1 (de) * | 1998-02-26 | 1999-09-09 | Wacker Chemie Gmbh | RTV-2 Siliconschäume mit niedrigem Druckverformungsrest |
| DE19905820A1 (de) * | 1998-10-27 | 2000-05-04 | Degussa | Schwefelfunktionelle Polyorganosilane |
| DE19904510A1 (de) | 1999-02-04 | 2000-08-10 | Wacker Chemie Gmbh | Siliconkautschuk |
| DE19957276A1 (de) | 1999-11-29 | 2001-10-11 | Abb Research Ltd | Additionsvernetzende Siliconkautschukmischungen |
| TWI242584B (en) | 2001-07-03 | 2005-11-01 | Lord Corp | High thermal conductivity spin castable potting compound |
| WO2003092890A2 (fr) * | 2002-04-29 | 2003-11-13 | Rhodia Chimie | Ensemble catalytique pour hydrosilylation, son procede de preparation et compositions silicone l'incorporant |
| GB0223108D0 (en) * | 2002-10-04 | 2002-11-13 | Johnson Matthey Plc | Hydrosilation catalyst |
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| WO2010078235A1 (en) | 2008-12-30 | 2010-07-08 | Bluestar Silicones | Coating compositions and textile fabrics coated therewith |
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| FR2957604A1 (fr) | 2010-03-22 | 2011-09-23 | Bluestar Silicones France | Composition silicone reticulable pour la realisation de revetements anti-adherents pour supports souples et additif promoteur d'accrochage contenu dans cette composition |
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| KR102756905B1 (ko) | 2019-02-22 | 2025-01-22 | 엘켐 실리콘즈 유에스에이 코포레이션 | 활성 성분 용출을 개선시키기 위한 약물 전달 실리콘 조성물 |
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| FR3099165A1 (fr) | 2019-07-25 | 2021-01-29 | Elkem Silicones France Sas | Composition silicone pour mousse elastomere. |
| JP7591035B2 (ja) | 2019-07-30 | 2024-11-27 | エルケム・シリコーンズ・ユーエスエイ・コーポレーション | 液体シリコーンゴム組成物から射出成形によりシリコーンゴム製品を製造するのに有用なプロセス及び装置組立体 |
| US12037458B2 (en) | 2019-09-06 | 2024-07-16 | Elkem Silicones USA Corp. | Process and premix for incorporating optical brighteners into a polymeric composition |
| WO2021123315A1 (en) | 2019-12-20 | 2021-06-24 | Elkem Silicones France Sas | Method for the additive manufacturing of a silicone elastomer article |
| EP4097190A1 (en) | 2020-01-30 | 2022-12-07 | Elkem Silicones USA Corp. | Article useful for circular economy and comprising a silicone elastomer with peelable and clean-releasing properties |
| MX2022009619A (es) | 2020-02-06 | 2022-11-07 | Elkem Silicones Usa Corp | Composiciones adhesivas de silicona altamente estirables y usos de las mismas como agentes de sellado/union. |
| US11643555B2 (en) | 2020-04-15 | 2023-05-09 | Elkem Silicones USA Corp. | Use of aryl group containing organopolysiloxane gums as additives to increase rheological behavior |
| US20230250283A1 (en) | 2020-06-25 | 2023-08-10 | Elkem Silicones France Sas | Thermally conductive silicone compositions |
| EP4189013A1 (fr) | 2020-07-29 | 2023-06-07 | Elkem Silicones France SAS | Composition silicone réticulable en élastomère comprenant un additif de tenue thermique |
| EP4005599A1 (en) | 2020-11-30 | 2022-06-01 | Elkem Silicones France SAS | Method for manufacturing a silicone elastomer article using a 3d printer |
| EP4039749A1 (en) | 2021-02-04 | 2022-08-10 | Elkem Silicones France SAS | A method of additive manufacture of a three-dimensional article made of a cured material and a gel like support for use in additive manufacturing |
| MX2024007344A (es) | 2021-12-17 | 2024-06-26 | Elkem Silicones France Sas | Metodo para preparar espuma de silicona. |
| FR3130816B1 (fr) | 2021-12-17 | 2023-12-15 | Elkem Silicones France Sas | Composition silicone réticulable par irradiation |
| CN118679061A (zh) | 2021-12-31 | 2024-09-20 | 埃肯有机硅（上海）有限公司 | 用于增材制造的双组份有机硅组合物 |
| JP2025515648A (ja) | 2022-05-03 | 2025-05-20 | エルケム・シリコーンズ・フランス・エスアエス | 食品との接触に適した物品及びその製造方法 |
| EP4273204A1 (en) | 2022-05-03 | 2023-11-08 | ELKEM SILICONES France SAS | Medical silicone pressure-sensitive adhesive composition |
| KR20250048278A (ko) | 2022-07-28 | 2025-04-08 | 엘켐 실리콘즈 유에스에이 코포레이션 | 실리콘 폼을 포함하는 임플란트 |
| WO2024067506A1 (en) | 2022-09-27 | 2024-04-04 | Elkem Silicones Shanghai Co., Ltd. | Method for post-treating an object |
| EP4344873A1 (en) | 2022-09-27 | 2024-04-03 | Elkem Silicones France SAS | Post-treatment of a 3d-printed elastomer silicone article |
| WO2024138379A1 (en) | 2022-12-27 | 2024-07-04 | Elkem Silicones Shanghai Co., Ltd. | Use of coating system comprising acrylic pre-coat and silicone top-coat in a paper-based food container and the paper-based food container coated with the coating system |
| FR3144920A1 (fr) | 2023-01-16 | 2024-07-19 | Elkem Silicones France Sas | Dispositif de protection passive contre l’incendie comprenant une mousse silicone |
| EP4410869A1 (en) | 2023-02-03 | 2024-08-07 | Elkem Silicones France SAS | New functionalized organopolysiloxane compounds, manufacturing method, and uses thereof |
| US20240400827A1 (en) | 2023-05-31 | 2024-12-05 | Gelest, Inc. | Siloxane composition for lower temperature adhesion |
| WO2025133478A1 (fr) | 2023-12-22 | 2025-06-26 | Elkem Silicones France Sas | Procédé de préparation d'un article comprenant une couche de mousse silicone |
| WO2025133477A1 (fr) | 2023-12-22 | 2025-06-26 | Elkem Silicones France Sas | Gel silicone adhésif à la peau |
| WO2025133479A1 (fr) | 2023-12-22 | 2025-06-26 | Elkem Silicones France Sas | Composition silicone réticulable par polyaddition pour la préparation d'élastomère silicone thermoconducteur |
| WO2025140702A1 (en) | 2023-12-29 | 2025-07-03 | Elkem Silicones Shanghai Co., Ltd. | Composite with high air-holding property |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3159662A (en) * | 1962-07-02 | 1964-12-01 | Gen Electric | Addition reaction |
| US3159601A (en) * | 1962-07-02 | 1964-12-01 | Gen Electric | Platinum-olefin complex catalyzed addition of hydrogen- and alkenyl-substituted siloxanes |
| US3516946A (en) * | 1967-09-29 | 1970-06-23 | Gen Electric | Platinum catalyst composition for hydrosilation reactions |
| US3775452A (en) * | 1971-04-28 | 1973-11-27 | Gen Electric | Platinum complexes of unsaturated siloxanes and platinum containing organopolysiloxanes |
| US4398010A (en) * | 1981-12-07 | 1983-08-09 | Sws Silicones Corporation | Method for accelerating the activity of a hydrosilation catalyst |
-
1981
- 1981-02-02 US US06/230,462 patent/US4394317A/en not_active Expired - Fee Related
- 1981-12-01 AU AU78128/81A patent/AU540319B2/en not_active Ceased
-
1982
- 1982-01-18 JP JP57005852A patent/JPS57136945A/ja active Granted
- 1982-01-21 CA CA000394595A patent/CA1180319A/en not_active Expired
- 1982-01-27 BR BR8200450A patent/BR8200450A/pt unknown
- 1982-02-02 EP EP82100708A patent/EP0057459B1/en not_active Expired
- 1982-02-02 AT AT82100708T patent/ATE11543T1/de not_active IP Right Cessation
- 1982-02-02 DE DE8282100708T patent/DE3262070D1/de not_active Expired
-
1983
- 1983-02-18 US US06/468,118 patent/US4450283A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57136945A (en) | 1982-08-24 |
| BR8200450A (pt) | 1982-11-30 |
| AU7812881A (en) | 1982-08-12 |
| EP0057459A1 (en) | 1982-08-11 |
| AU540319B2 (en) | 1984-11-08 |
| EP0057459B1 (en) | 1985-01-30 |
| CA1180319A (en) | 1985-01-02 |
| DE3262070D1 (en) | 1985-03-14 |
| US4450283A (en) | 1984-05-22 |
| ATE11543T1 (de) | 1985-02-15 |
| US4394317A (en) | 1983-07-19 |
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