CN1050144C - 星形聚二甲基硅氧烷嵌段共聚物及其制备方法 - Google Patents
星形聚二甲基硅氧烷嵌段共聚物及其制备方法 Download PDFInfo
- Publication number
- CN1050144C CN1050144C CN93112998A CN93112998A CN1050144C CN 1050144 C CN1050144 C CN 1050144C CN 93112998 A CN93112998 A CN 93112998A CN 93112998 A CN93112998 A CN 93112998A CN 1050144 C CN1050144 C CN 1050144C
- Authority
- CN
- China
- Prior art keywords
- branches
- branch
- block copolymer
- coupler
- radial block
- 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 - Fee Related
Links
- -1 polydimethylsiloxane Polymers 0.000 title claims abstract description 19
- 229920001400 block copolymer Polymers 0.000 title claims abstract description 18
- 239000004205 dimethyl polysiloxane Substances 0.000 title claims abstract description 11
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 22
- 229920000642 polymer Polymers 0.000 claims abstract description 15
- 150000001993 dienes Chemical class 0.000 claims abstract description 13
- HTDJPCNNEPUOOQ-UHFFFAOYSA-N hexamethylcyclotrisiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O1 HTDJPCNNEPUOOQ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract 5
- 230000000379 polymerizing effect Effects 0.000 claims abstract 3
- 238000006243 chemical reaction Methods 0.000 claims description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 11
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical group C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 10
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical group CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 10
- 239000004793 Polystyrene Substances 0.000 claims description 10
- 239000000178 monomer Substances 0.000 claims description 10
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 9
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 229920002223 polystyrene Polymers 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- 239000007822 coupling agent Substances 0.000 claims 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 abstract description 9
- 230000008878 coupling Effects 0.000 abstract description 7
- 238000010168 coupling process Methods 0.000 abstract description 7
- 229920001577 copolymer Polymers 0.000 abstract description 5
- 229920002554 vinyl polymer Polymers 0.000 abstract description 3
- 239000000126 substance Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 229920013730 reactive polymer Polymers 0.000 description 9
- XZKRXPZXQLARHH-UHFFFAOYSA-N buta-1,3-dienylbenzene Chemical group C=CC=CC1=CC=CC=C1 XZKRXPZXQLARHH-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 239000003205 fragrance Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 3
- 229920005601 base polymer Polymers 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 125000005401 siloxanyl group Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000012815 thermoplastic material Substances 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- MPGOMZYTJXESSF-UHFFFAOYSA-N 1,2,5-tris(ethenyl)-3,7-diethylnaphthalene Chemical compound C1=C(CC)C(C=C)=C(C=C)C2=CC(CC)=CC(C=C)=C21 MPGOMZYTJXESSF-UHFFFAOYSA-N 0.000 description 1
- FWFAJEYKHANIJP-UHFFFAOYSA-N 1,3,5-tris(ethenyl)naphthalene Chemical compound C1=CC=C(C=C)C2=CC(C=C)=CC(C=C)=C21 FWFAJEYKHANIJP-UHFFFAOYSA-N 0.000 description 1
- SZEZDFQBIICMNO-UHFFFAOYSA-N 1,3-bis(ethenyl)-5-(4-ethenylphenyl)benzene Chemical group C1=CC(C=C)=CC=C1C1=CC(C=C)=CC(C=C)=C1 SZEZDFQBIICMNO-UHFFFAOYSA-N 0.000 description 1
- TUDTVAXRTPHZAJ-UHFFFAOYSA-N 1,3-bis(ethenyl)naphthalene Chemical compound C1=CC=CC2=CC(C=C)=CC(C=C)=C21 TUDTVAXRTPHZAJ-UHFFFAOYSA-N 0.000 description 1
- WEERVPDNCOGWJF-UHFFFAOYSA-N 1,4-bis(ethenyl)benzene Chemical compound C=CC1=CC=C(C=C)C=C1 WEERVPDNCOGWJF-UHFFFAOYSA-N 0.000 description 1
- HFOCWQKBVRVPGX-UHFFFAOYSA-N 1,7,8-tributyl-2,4-bis(ethenyl)naphthalene Chemical compound C=CC1=CC(C=C)=C(CCCC)C2=C(CCCC)C(CCCC)=CC=C21 HFOCWQKBVRVPGX-UHFFFAOYSA-N 0.000 description 1
- FTUDIUREWUBVKL-UHFFFAOYSA-N 1,8-bis(ethenyl)naphthalene Chemical compound C1=CC(C=C)=C2C(C=C)=CC=CC2=C1 FTUDIUREWUBVKL-UHFFFAOYSA-N 0.000 description 1
- JVXPEVSEOVECRV-UHFFFAOYSA-N 2,4-bis(ethenyl)-1-phenylbenzene Chemical group C=CC1=CC(C=C)=CC=C1C1=CC=CC=C1 JVXPEVSEOVECRV-UHFFFAOYSA-N 0.000 description 1
- QTTAWIGVQMSWMV-UHFFFAOYSA-N 3,4-dimethylhexa-1,3-diene Chemical compound CCC(C)=C(C)C=C QTTAWIGVQMSWMV-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
- CJSBUWDGPXGFGA-UHFFFAOYSA-N 4-methylpenta-1,3-diene Chemical compound CC(C)=CC=C CJSBUWDGPXGFGA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- 241000237502 Ostreidae Species 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Chemical group 0.000 description 1
- 150000001298 alcohols Chemical group 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 125000000217 alkyl 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
- 239000002585 base Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000012661 block copolymerization Methods 0.000 description 1
- PCWZHTGDXLRULT-UHFFFAOYSA-N buta-1,3-dienylbenzene styrene Chemical compound C(=C)C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 PCWZHTGDXLRULT-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 235000020636 oyster Nutrition 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
Classifications
-
- 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
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/442—Block-or graft-polymers containing polysiloxane sequences containing vinyl polymer sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Silicon Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US996,285 | 1992-12-23 | ||
| US07/996,285 US5276095A (en) | 1992-12-23 | 1992-12-23 | Star block copolymers of vinyl aromatic hydrocarbons and polydimethylsiloxane and method of synthesis |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1105036A CN1105036A (zh) | 1995-07-12 |
| CN1050144C true CN1050144C (zh) | 2000-03-08 |
Family
ID=25542727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN93112998A Expired - Fee Related CN1050144C (zh) | 1992-12-23 | 1993-12-21 | 星形聚二甲基硅氧烷嵌段共聚物及其制备方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5276095A (enExample) |
| EP (1) | EP0675916B1 (enExample) |
| JP (1) | JPH08504865A (enExample) |
| KR (1) | KR100296248B1 (enExample) |
| CN (1) | CN1050144C (enExample) |
| AT (1) | ATE151793T1 (enExample) |
| AU (1) | AU5834294A (enExample) |
| BR (1) | BR9307703A (enExample) |
| DE (1) | DE69309961T2 (enExample) |
| DK (1) | DK0675916T3 (enExample) |
| ES (1) | ES2100687T3 (enExample) |
| GR (1) | GR3023844T3 (enExample) |
| TW (1) | TW299339B (enExample) |
| WO (1) | WO1994014876A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU663661B1 (en) * | 1994-06-03 | 1995-10-12 | Morton International, Inc. | Impact-resistant acrylic powder coatings |
| US5773521A (en) * | 1995-12-19 | 1998-06-30 | Shell Oil Company | Coupling to produce inside-out star polymers with expanded cores |
| US5663245A (en) * | 1996-03-22 | 1997-09-02 | The University Of Akron | Star polymers having a well-defined siloxane core and multiple polyisobutylene arms and a method for the synthesis thereof |
| US5840814A (en) * | 1996-08-07 | 1998-11-24 | The University Of Akron | Multi-arm star polymers having a well-defined core and methods for the synthesis thereof |
| US5789516A (en) * | 1997-04-07 | 1998-08-04 | Dow Corning Corporation | Method of making silicone-organic block copolymers |
| US6090902A (en) * | 1998-12-21 | 2000-07-18 | Dow Corning Corporation | Organopolysiloxane-modified graft copolymers |
| FR2802542A1 (fr) * | 1999-12-20 | 2001-06-22 | Michelin Soc Tech | Composition de caoutchouc vulcanisable pour la fabrication d'un pneumatique et pneumatique dont la bande de roulement comprend une telle composition |
| CN100503719C (zh) * | 2001-07-18 | 2009-06-24 | 旭化成化学株式会社 | 聚合物组合物 |
| DE10135305A1 (de) * | 2001-07-19 | 2003-02-06 | Wacker Chemie Gmbh | Verzweigte Organosiloxan(co)polymere |
| DE50201143D1 (de) * | 2001-07-19 | 2004-11-04 | Wacker Chemie Gmbh | Verzweigte Organosiloxan(co)polymere und deren Verwendung als Antimisting Additive für Siliconbeschichtungszusammensetzungen |
| DE102004051034A1 (de) * | 2004-10-20 | 2006-04-27 | Hella Kgaa Hueck & Co. | Beschichtungsmasse zur Herstellung einer hydrophilen Beschichtung |
| WO2007051252A1 (en) * | 2005-11-03 | 2007-05-10 | The University Of Melbourne | Porous polymeric materials and polymer particles for preparation thereof |
| CN102120807B (zh) * | 2010-01-09 | 2012-09-12 | 中国石油化工集团公司 | 一种苯乙烯-共轭二烯烃星型嵌段共聚物及其制备方法 |
| CN102140170B (zh) * | 2010-12-28 | 2012-12-05 | 蓝星化工新材料股份有限公司江西星火有机硅厂 | 高分子量全甲基硅油的制备工艺 |
| US20150065647A1 (en) * | 2013-08-28 | 2015-03-05 | The Goodyear Tire & Rubber Company | Functionalized polymer, rubber composition and pneumatic tire |
| CN104108216B (zh) * | 2014-07-04 | 2016-02-24 | 常州大学 | 一种采用星形共聚物改性增透聚酯薄膜的方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0420686A2 (en) * | 1989-09-29 | 1991-04-03 | E.I. Du Pont De Nemours And Company | Hybrid acrylic star polymers with polysiloxane cores |
| JPH03190911A (ja) * | 1989-12-20 | 1991-08-20 | Nippon Paint Co Ltd | 星型共重合体およびその製造方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3051684A (en) * | 1959-03-26 | 1962-08-28 | Directors Of The University Of | Organosiloxane polymers containing polydiene blocks |
| US3483270A (en) * | 1966-04-11 | 1969-12-09 | Gen Electric | Stereospecific organosiloxane-macromolecular hydrocarbon block copolymers |
| GB1257304A (enExample) * | 1968-03-29 | 1971-12-15 | ||
| US3644322A (en) * | 1969-02-03 | 1972-02-22 | Phillips Petroleum Co | Polymerization of conjugated dienes and monovinyl aromatic compounds with multifunctional polymerization initiators |
| US3665052A (en) * | 1970-08-25 | 1972-05-23 | Dow Corning | Method of preparing a block copolymer containing a poly-alpha-methylstyrene block and a polydiorganosiloxane block |
| US3760030A (en) * | 1971-06-02 | 1973-09-18 | Gen Electric | Multiple sequence block copolymers of silicones and styrene |
| US3928490A (en) * | 1972-03-07 | 1975-12-23 | Firestone Tire & Rubber Co | Block polymers of polysiloxanes and polybutadiene |
| US3985830B1 (en) * | 1974-07-15 | 1998-03-03 | Univ Akron | Star polymers and process for the preparation thereof |
| CA1065334A (en) * | 1974-12-16 | 1979-10-30 | Eugene R. Martin | Silylated polymers and silylated organic-organopolysiloxane block copolymers |
| US4273896A (en) * | 1978-07-12 | 1981-06-16 | Sws Silicones Corporation | Silylated polymers and silylated organic-organopolysiloxane block copolymers |
| FR2436155A1 (fr) * | 1978-09-13 | 1980-04-11 | Rhone Poulenc Ind | Elastomeres thermoplastiques polystyreniques-diorganopolysiloxaniques |
| US4768750A (en) * | 1987-01-16 | 1988-09-06 | Fisher Controls International, Inc. | Valve joint connection |
| US5212249A (en) * | 1991-10-28 | 1993-05-18 | Shell Oil Company | Method for preparing asymmetric radial polymers |
-
1992
- 1992-12-23 US US07/996,285 patent/US5276095A/en not_active Expired - Lifetime
-
1993
- 1993-11-29 TW TW082110051A patent/TW299339B/zh active
- 1993-12-21 CN CN93112998A patent/CN1050144C/zh not_active Expired - Fee Related
- 1993-12-22 BR BR9307703-3A patent/BR9307703A/pt not_active IP Right Cessation
- 1993-12-22 DK DK94904185.9T patent/DK0675916T3/da active
- 1993-12-22 DE DE69309961T patent/DE69309961T2/de not_active Expired - Fee Related
- 1993-12-22 AU AU58342/94A patent/AU5834294A/en not_active Abandoned
- 1993-12-22 KR KR1019950702635A patent/KR100296248B1/ko not_active Expired - Fee Related
- 1993-12-22 WO PCT/EP1993/003692 patent/WO1994014876A1/en not_active Ceased
- 1993-12-22 JP JP6514835A patent/JPH08504865A/ja active Pending
- 1993-12-22 AT AT94904185T patent/ATE151793T1/de not_active IP Right Cessation
- 1993-12-22 ES ES94904185T patent/ES2100687T3/es not_active Expired - Lifetime
- 1993-12-22 EP EP94904185A patent/EP0675916B1/en not_active Expired - Lifetime
-
1997
- 1997-06-19 GR GR970401482T patent/GR3023844T3/el unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0420686A2 (en) * | 1989-09-29 | 1991-04-03 | E.I. Du Pont De Nemours And Company | Hybrid acrylic star polymers with polysiloxane cores |
| JPH03190911A (ja) * | 1989-12-20 | 1991-08-20 | Nippon Paint Co Ltd | 星型共重合体およびその製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU5834294A (en) | 1994-07-19 |
| EP0675916A1 (en) | 1995-10-11 |
| ES2100687T3 (es) | 1997-06-16 |
| WO1994014876A1 (en) | 1994-07-07 |
| ATE151793T1 (de) | 1997-05-15 |
| DK0675916T3 (enExample) | 1997-05-26 |
| DE69309961D1 (de) | 1997-05-22 |
| TW299339B (enExample) | 1997-03-01 |
| BR9307703A (pt) | 1999-08-31 |
| KR100296248B1 (ko) | 2001-10-24 |
| EP0675916B1 (en) | 1997-04-16 |
| DE69309961T2 (de) | 1997-07-24 |
| US5276095A (en) | 1994-01-04 |
| GR3023844T3 (en) | 1997-09-30 |
| JPH08504865A (ja) | 1996-05-28 |
| KR960700293A (ko) | 1996-01-19 |
| CN1105036A (zh) | 1995-07-12 |
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