CA1240093A - Process for the continuous manufacture of silicone gums - Google Patents
Process for the continuous manufacture of silicone gumsInfo
- Publication number
- CA1240093A CA1240093A CA000473933A CA473933A CA1240093A CA 1240093 A CA1240093 A CA 1240093A CA 000473933 A CA000473933 A CA 000473933A CA 473933 A CA473933 A CA 473933A CA 1240093 A CA1240093 A CA 1240093A
- Authority
- CA
- Canada
- Prior art keywords
- set forth
- mixture
- resulting
- chainstopping
- catalyst
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 65
- 230000008569 process Effects 0.000 title claims abstract description 63
- 229920001296 polysiloxane Polymers 0.000 title abstract description 22
- 238000004519 manufacturing process Methods 0.000 title abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 40
- 239000003054 catalyst Substances 0.000 claims abstract description 34
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 34
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 32
- 239000000178 monomer Substances 0.000 claims abstract description 30
- 229920000642 polymer Polymers 0.000 claims abstract description 30
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 17
- 238000002156 mixing Methods 0.000 claims abstract description 13
- 230000000379 polymerizing effect Effects 0.000 claims abstract 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- IALUUOKJPBOFJL-UHFFFAOYSA-N potassium oxidosilane Chemical group [K+].[SiH3][O-] IALUUOKJPBOFJL-UHFFFAOYSA-N 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 9
- 230000003068 static effect Effects 0.000 claims description 9
- YIKQLNRXIWIZFA-UHFFFAOYSA-N silyl dihydrogen phosphate Chemical group OP(O)(=O)O[SiH3] YIKQLNRXIWIZFA-UHFFFAOYSA-N 0.000 claims description 8
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 claims description 7
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 238000006386 neutralization reaction Methods 0.000 claims description 4
- 238000004898 kneading Methods 0.000 claims description 3
- 239000002808 molecular sieve Substances 0.000 claims description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 3
- 125000005389 trialkylsiloxy group Chemical group 0.000 claims description 3
- 230000009471 action Effects 0.000 claims description 2
- 238000004064 recycling Methods 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 30
- -1 polysiloxanes Polymers 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000004122 cyclic group Chemical group 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 9
- 229920002554 vinyl polymer Polymers 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 5
- 239000003039 volatile agent Substances 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000010924 continuous production Methods 0.000 description 4
- 229960004838 phosphoric acid Drugs 0.000 description 4
- 235000011007 phosphoric acid Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 239000004614 Process Aid Substances 0.000 description 3
- 238000010923 batch production Methods 0.000 description 3
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 229920002379 silicone rubber Polymers 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 102100038916 Caspase-5 Human genes 0.000 description 2
- 101100112336 Homo sapiens CASP5 gene Proteins 0.000 description 2
- 101100273286 Mus musculus Casp4 gene Proteins 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229920005573 silicon-containing polymer Polymers 0.000 description 2
- 239000004945 silicone rubber Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VMAWODUEPLAHOE-UHFFFAOYSA-N 2,4,6,8-tetrakis(ethenyl)-2,4,6,8-tetramethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound C=C[Si]1(C)O[Si](C)(C=C)O[Si](C)(C=C)O[Si](C)(C=C)O1 VMAWODUEPLAHOE-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 101150034533 ATIC gene Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- OUKMJYHQZXBWNQ-UHFFFAOYSA-N cesium oxidosilane Chemical compound [Cs+].[SiH3][O-] OUKMJYHQZXBWNQ-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 229920005645 diorganopolysiloxane polymer Polymers 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- KBJKWYZQIJZAOZ-UHFFFAOYSA-N lithium;oxidosilane Chemical compound [Li+].[SiH3][O-] KBJKWYZQIJZAOZ-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- LUVCTYHBTXSAMX-UHFFFAOYSA-N tris(2-chloroethyl) phosphite Chemical compound ClCCOP(OCCCl)OCCCl LUVCTYHBTXSAMX-UHFFFAOYSA-N 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
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/18—Stationary reactors having moving elements inside
- B01J19/20—Stationary reactors having moving elements inside in the form of helices, e.g. screw reactors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Silicon Polymers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/584,060 US4551515A (en) | 1984-02-27 | 1984-02-27 | Process for the continuous manufacture of silicone gums |
| US584,060 | 1984-02-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1240093A true CA1240093A (en) | 1988-08-02 |
Family
ID=24335766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000473933A Expired CA1240093A (en) | 1984-02-27 | 1985-02-08 | Process for the continuous manufacture of silicone gums |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4551515A (enExample) |
| JP (1) | JPS60202124A (enExample) |
| CA (1) | CA1240093A (enExample) |
| GB (1) | GB2154596A (enExample) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0610262B2 (ja) * | 1985-05-28 | 1994-02-09 | 東レ・ダウコーニング・シリコーン株式会社 | シリコ−ン重合体−充填剤混合物の製造方法 |
| DE3519411A1 (de) * | 1985-05-30 | 1986-12-04 | Wacker-Chemie GmbH, 8000 München | Kontinuierliches verfahren zur aenderung des molekulargewichts von organosiliciumverbindungen |
| US4701491A (en) * | 1986-10-27 | 1987-10-20 | Dow Corning Corporation | Silicone extrusion stock |
| US4719276A (en) * | 1986-10-27 | 1988-01-12 | Dow Corning Corporation | Neutralization of catalyst in polymerization of polydiorganosiloxane |
| US4780519A (en) * | 1986-10-27 | 1988-10-25 | Dow Corning Corporation | Method of producing polydiorganosiloxane gum |
| US4766192A (en) * | 1987-07-10 | 1988-08-23 | Dow Corning Corporation | Silicone polymer termination |
| US4766191A (en) * | 1987-07-10 | 1988-08-23 | Dow Corning Corporation | Silicone polymer termination |
| DE3914912A1 (de) * | 1989-05-05 | 1990-11-08 | Wacker Chemie Gmbh | Verfahren zur kontinuierlichen herstellung von hochmolekularen organosiliciumverbindungen |
| US5079291A (en) * | 1989-11-20 | 1992-01-07 | General Electric Company | Polar aprotic catalysts for formation of fluorosilicone fluids |
| DE4007312C2 (de) * | 1990-03-08 | 2000-04-27 | Basf Ag | Verfahren zur Herstellung von feinteiligen, wasserlöslichen, Vinylamin-Einheiten enthaltenden Polymerisaten |
| US5173558A (en) * | 1991-05-20 | 1992-12-22 | Dow Corning Corporation | Base catalyzed preparation of polyorganosiloxanes with controlled low levels of hydroxy substitution |
| EP0546747A1 (en) * | 1991-12-05 | 1993-06-16 | General Electric Company | Polymerisation process |
| US5481014A (en) * | 1995-05-08 | 1996-01-02 | Dow Corning Corporation | Silyl phosphonate as stabilizing agent for polydiorganosiloxanes |
| US5710300A (en) * | 1997-04-11 | 1998-01-20 | Dow Corning Corporation | Siloxy phosphonate as stabilizing agent for polydiorganosiloxanes |
| US6103847A (en) * | 1997-05-27 | 2000-08-15 | Witco Corporation | Siloxane-polyether copolymers with unsaturated functionalities, and process for making them |
| US6103839A (en) * | 1998-05-11 | 2000-08-15 | Nalco Chemical Company | Horizontally flowing continuous free radical polymerization process for manufacturing water-soluble polymers from monomers in aqueous solution |
| GB9818539D0 (en) * | 1998-08-26 | 1998-10-21 | Dow Corning | Process for producing a silicone polymer |
| GB9818541D0 (en) * | 1998-08-26 | 1998-10-21 | Dow Corning | Continuous process for producing a silicone polymer |
| GB9818543D0 (en) * | 1998-08-26 | 1998-10-21 | Dow Corning | Continuous process for producing a silicone polymer |
| JP3546728B2 (ja) | 1998-12-02 | 2004-07-28 | 信越化学工業株式会社 | オルガノポリシロキサンガムの連続製造方法 |
| TW500768B (en) * | 1998-12-02 | 2002-09-01 | Shinetsu Chemical Co | Preparation of organopolysiloxane gum |
| JP2004217850A (ja) * | 2003-01-17 | 2004-08-05 | Dow Corning Toray Silicone Co Ltd | オルガノポリシロキサン組成物および硬化性オルガノポリシロキサン組成物 |
| DE102004014218A1 (de) * | 2004-03-23 | 2005-10-13 | Wacker-Chemie Gmbh | Verfahren zur Herstellung von aminofunktionellen Organopolysiloxanen |
| CN100347264C (zh) * | 2005-12-05 | 2007-11-07 | 叶照光 | 一种硅酮密封结构胶全自动生产、灌装、分装方法 |
| JP5207627B2 (ja) * | 2006-12-27 | 2013-06-12 | 東レ・ダウコーニング株式会社 | オルガノポリシロキサンの熱安定性を改善する方法およびオルガノポリシロキサン混合物 |
| DE102007036069A1 (de) * | 2007-08-01 | 2009-02-05 | Wacker Chemie Ag | Mehrstufiges Verfahren zur Herstellung von Aminoalkylgruppen aufweisenden Organopolysiloxanen |
| CN102421828B (zh) | 2009-05-13 | 2014-12-10 | 陶氏康宁公司 | 聚合和乳化硅氧烷的连续法 |
| CN102070785A (zh) * | 2010-11-26 | 2011-05-25 | 杭州赛默科技有限公司 | 一种羟基封端聚甲基苯基硅氧烷的制备方法 |
| CN103459027A (zh) * | 2011-03-31 | 2013-12-18 | 道康宁公司 | 包含膦酸酯催化剂的组合物以及制备和使用组合物的方法 |
| CN102492145A (zh) * | 2011-12-07 | 2012-06-13 | 江苏宏达新材料股份有限公司 | 一种高分子量甲基苯基硅橡胶生胶的制备方法 |
| CN102924721B (zh) * | 2012-11-22 | 2013-12-25 | 深圳市森日有机硅材料有限公司 | 一种乙烯基硅油的连续化制备方法 |
| CN105111445A (zh) * | 2015-09-30 | 2015-12-02 | 桂林健评环保节能产品开发有限公司 | 一种led灌封胶用甲基苯基硅油及其制备方法 |
| JP2025516012A (ja) | 2022-05-09 | 2025-05-23 | ダウ シリコーンズ コーポレーション | シロキサンポリマーの重合 |
| CN115417991B (zh) * | 2022-09-06 | 2024-02-09 | 江西蓝星星火有机硅有限公司 | 连续生产有机聚硅氧烷的聚合-终止装置及方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2546036A (en) * | 1946-06-11 | 1951-03-20 | Gen Electric | Method of preparation of dimethyl silicone gums |
| US2634252A (en) * | 1949-05-25 | 1953-04-07 | Dow Corning | Method of polymerizing organosiloxanes with alkoxides and alcohol-hydroxide complexes |
| FR1583057A (enExample) * | 1967-05-09 | 1969-10-17 | ||
| US3433765A (en) * | 1967-08-07 | 1969-03-18 | Stauffer Chemical Co | Method for the production of silicone gums |
| US3803084A (en) * | 1968-03-23 | 1974-04-09 | Bayer Ag | Process for the production of high-polymer organo-siloxanes |
| GB1436883A (en) * | 1972-07-20 | 1976-05-26 | Gen Electric | Process for the production of silanol-stopped diorganopoly siloxanes |
| DE2705563C2 (de) * | 1977-02-10 | 1982-10-14 | Bayer Ag, 5090 Leverkusen | Verfahren zur kontinuierlichen Herstellung von hochviskosen Polydiorganosiloxanen |
| AU5900880A (en) * | 1979-06-18 | 1981-01-08 | General Electric Company | Continuous manufacture of siloxane polymers |
| JPS5626248A (en) * | 1979-08-10 | 1981-03-13 | Kawasaki Steel Corp | Observing device for x-ray kossel diffraction pattern |
| GB2052539B (en) * | 1980-06-03 | 1984-06-20 | Gen Electric | Process for the continuous manufacture of diorganopolysiloxane polymers |
-
1984
- 1984-02-27 US US06/584,060 patent/US4551515A/en not_active Expired - Lifetime
- 1984-10-17 GB GB08426177A patent/GB2154596A/en not_active Withdrawn
-
1985
- 1985-02-08 CA CA000473933A patent/CA1240093A/en not_active Expired
- 1985-02-15 JP JP60026619A patent/JPS60202124A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60202124A (ja) | 1985-10-12 |
| GB2154596A (en) | 1985-09-11 |
| GB8426177D0 (en) | 1984-11-21 |
| JPH0319250B2 (enExample) | 1991-03-14 |
| US4551515A (en) | 1985-11-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |