JP6594305B2 - モノビニル芳香族共役ジエンブロックコポリマー、および該ブロックコポリマーとモノビニルアレーンアクリラートコポリマーとを含むポリマー組成物 - Google Patents
モノビニル芳香族共役ジエンブロックコポリマー、および該ブロックコポリマーとモノビニルアレーンアクリラートコポリマーとを含むポリマー組成物 Download PDFInfo
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- JP6594305B2 JP6594305B2 JP2016524769A JP2016524769A JP6594305B2 JP 6594305 B2 JP6594305 B2 JP 6594305B2 JP 2016524769 A JP2016524769 A JP 2016524769A JP 2016524769 A JP2016524769 A JP 2016524769A JP 6594305 B2 JP6594305 B2 JP 6594305B2
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- Prior art keywords
- block
- conjugated diene
- block copolymer
- copolymer
- polymer composition
- 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.)
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- 229920001400 block copolymer Polymers 0.000 title claims description 105
- 239000000203 mixture Substances 0.000 title claims description 82
- 150000001993 dienes Chemical class 0.000 title claims description 81
- 229920000642 polymer Polymers 0.000 title claims description 79
- 125000003118 aryl group Chemical group 0.000 title claims description 57
- 229920001577 copolymer Polymers 0.000 title claims description 26
- 239000000178 monomer Substances 0.000 claims description 88
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 72
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 68
- 238000006116 polymerization reaction Methods 0.000 claims description 33
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims description 25
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 19
- 229920007962 Styrene Methyl Methacrylate Polymers 0.000 claims description 18
- ADFPJHOAARPYLP-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;styrene Chemical group COC(=O)C(C)=C.C=CC1=CC=CC=C1 ADFPJHOAARPYLP-UHFFFAOYSA-N 0.000 claims description 18
- 229920002554 vinyl polymer Polymers 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 239000003505 polymerization initiator Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 239000011591 potassium Substances 0.000 claims description 11
- 229910052700 potassium Inorganic materials 0.000 claims description 9
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 7
- HLKWWJWIDARXEW-UHFFFAOYSA-N potassium;2-methylbutan-1-olate Chemical compound [K+].CCC(C)C[O-] HLKWWJWIDARXEW-UHFFFAOYSA-N 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 4
- PSGOPFRAYAIOMX-UHFFFAOYSA-N potassium;2,3-dimethylpentan-3-olate Chemical compound [K+].CCC(C)([O-])C(C)C PSGOPFRAYAIOMX-UHFFFAOYSA-N 0.000 claims description 4
- 159000000001 potassium salts Chemical class 0.000 claims description 3
- RGTULLOKMOQGAQ-UHFFFAOYSA-N potassium;3,7-dimethyloctan-3-olate Chemical compound [K+].CCC(C)([O-])CCCC(C)C RGTULLOKMOQGAQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 2
- 238000005516 engineering process Methods 0.000 claims description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 1
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- 238000000465 moulding Methods 0.000 claims 1
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- 239000007822 coupling agent Substances 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 2
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
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- 125000001931 aliphatic group Chemical group 0.000 description 2
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- 230000005540 biological transmission Effects 0.000 description 2
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- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
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- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
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- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
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- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
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- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 239000011414 polymer cement Substances 0.000 description 1
- 150000003109 potassium Chemical class 0.000 description 1
- ZRLVQFQTCMUIRM-UHFFFAOYSA-N potassium;2-methylbutan-2-olate Chemical compound [K+].CCC(C)(C)[O-] ZRLVQFQTCMUIRM-UHFFFAOYSA-N 0.000 description 1
- XFLAKIAEOPDWCP-UHFFFAOYSA-N potassium;2-methylhexan-1-olate Chemical compound [K+].CCCCC(C)C[O-] XFLAKIAEOPDWCP-UHFFFAOYSA-N 0.000 description 1
- LZDGSLFCXXQIQC-UHFFFAOYSA-N potassium;3-ethylpentan-3-olate Chemical compound [K+].CCC([O-])(CC)CC LZDGSLFCXXQIQC-UHFFFAOYSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
-
- 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
- C08F297/02—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type
- C08F297/04—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type polymerising vinyl aromatic monomers and conjugated dienes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/04—Homopolymers or copolymers of styrene
- C08L25/08—Copolymers of styrene
- C08L25/14—Copolymers of styrene with unsaturated esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/06—Polymer mixtures characterised by other features having improved processability or containing aids for moulding methods
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)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13175483.0 | 2013-07-08 | ||
| EP13175483 | 2013-07-08 | ||
| PCT/EP2014/064411 WO2015004043A1 (en) | 2013-07-08 | 2014-07-07 | Mono vinyl aromatic conjugated diene block copolymer and polymer composition comprising said block copolymer and a mono vinylarene acrylate copolymer |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016524027A JP2016524027A (ja) | 2016-08-12 |
| JP2016524027A5 JP2016524027A5 (enExample) | 2017-06-15 |
| JP6594305B2 true JP6594305B2 (ja) | 2019-10-23 |
Family
ID=48745832
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016524769A Expired - Fee Related JP6594305B2 (ja) | 2013-07-08 | 2014-07-07 | モノビニル芳香族共役ジエンブロックコポリマー、および該ブロックコポリマーとモノビニルアレーンアクリラートコポリマーとを含むポリマー組成物 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9845374B2 (enExample) |
| EP (1) | EP3019542B1 (enExample) |
| JP (1) | JP6594305B2 (enExample) |
| CN (1) | CN105377924B (enExample) |
| WO (1) | WO2015004043A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4134046A1 (en) | 2013-10-15 | 2023-02-15 | TechMah Medical LLC | Method of designing a patient-specific placement guide |
| JP6122464B2 (ja) * | 2015-05-15 | 2017-04-26 | デンカ株式会社 | チューブラー成形用材料及びそれを使用した熱収縮フィルム |
| ES2909554T3 (es) | 2016-11-21 | 2022-05-09 | Ineos Styrolution Group Gmbh | Mezclas de copolímeros de estireno-butadieno (SBC) con bloques aleatorios y SMMA |
| KR102672998B1 (ko) * | 2018-04-16 | 2024-06-05 | 이네오스 스티롤루션 그룹 게엠베하 | 초고 흐름 아크릴로니트릴 부타디엔 스티렌 코폴리머 조성물 |
| US20220033593A1 (en) | 2018-09-21 | 2022-02-03 | Ineos Styrolution Group Gmbh | Thermoplastic polymer powders and use thereof for selective laser sintering |
| EP3853008A1 (de) | 2018-09-21 | 2021-07-28 | INEOS Styrolution Group GmbH | Verfahren des selektiven lasersinterns unter verwendung von thermoplastischen polymerpulvern |
| CN113348207B (zh) * | 2019-01-24 | 2023-05-12 | 旭化成株式会社 | 嵌段共聚物组合物、成型品、成型品的制造方法、以及调整成型品的雾度值的方法 |
| JP2024521493A (ja) * | 2021-06-16 | 2024-05-31 | イネオス・スタイロリューション・グループ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | Ｓｍｍａコポリマーおよびｓｂｃブロックコポリマーを含む高い透明度および延性のある成形用組成物 |
| EP4479473A1 (en) * | 2022-02-14 | 2024-12-25 | INEOS Styrolution Group GmbH | High clarity and ductile molding composition comprising a smma copolymer, a sbc-block copolymer and at least one light stabilizer |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4386190A (en) * | 1982-08-23 | 1983-05-31 | Phillips Petroleum Company | Polymer blend of diene/vinyl aromatic block copolymer and styrene/acrylate copolymer |
| LU86698A1 (fr) * | 1986-12-04 | 1988-07-14 | Labofina Sa | Procede pour fabriquer des copolymeres blocs transparents |
| IT1227901B (it) | 1988-12-23 | 1991-05-14 | Enichem Elastomers | Composizioni polimeriche e loro metodo di preparazione |
| US5304598A (en) * | 1988-12-23 | 1994-04-19 | Enichem Elastomeri S.P.A. | Polymeric compositions and method for preparing them |
| DE4420952A1 (de) | 1994-06-17 | 1995-12-21 | Basf Ag | Thermoplastisches Elastomer |
| US5777030A (en) | 1996-09-27 | 1998-07-07 | Phillips Petroleum Company | Blends of a styrenic polymer and monovinylaren/conjugated diene block copolymers |
| DE19806785A1 (de) * | 1998-02-18 | 1999-08-19 | Basf Ag | Verfahren zur Herstellung von Blockcopolymeren durch retardierten anionischen Polymerisation |
| DE69941620D1 (de) | 1998-08-03 | 2009-12-17 | Asahi Chemical Ind | Lineares blockcopolymer und harzzusammensetzung die dieses enthält |
| US6326127B1 (en) | 1998-12-31 | 2001-12-04 | Kraton Polymers U.S. Llc | Photo-curable polymer composition and flexographic printing plates containing the same |
| US6593430B1 (en) | 1999-03-27 | 2003-07-15 | Basf Aktiengesellschaft | Transparent, impact-resistant polystyrene on a styrene-butadiene block copolymer basis |
| DE19914075A1 (de) | 1999-03-27 | 2000-09-28 | Basf Ag | Glasklares, schlagzähes Polystyrol auf Basis von Styrol-Butadien-Blockcopolymeren |
| WO2002038642A1 (fr) * | 2000-11-10 | 2002-05-16 | Denki Kagaku Kogyo Kabushiki Kaisha | Copolymere bloc, sa composition et films en etant faits |
| US6916879B2 (en) * | 2001-05-18 | 2005-07-12 | Basf Aktiengesellschaft | Core-hydrogenated block copolymers having an asymmetric structure |
| US7193014B2 (en) | 2004-02-20 | 2007-03-20 | Chevron Phillips Chemical Company, Lp | Binary and ternary blends comprising monovinylarene/conjugated diene block copolymers and monovinylarene/alkyl (meth)acrylate copolymers |
| US20060100371A1 (en) | 2004-11-08 | 2006-05-11 | Foss David R | Polymer blends of a monovinylarene conjugated diene block copolymer and a monvinylarene acrylate copolymer |
| US7776965B2 (en) | 2004-11-09 | 2010-08-17 | Chevron Phillips Chemical Company, Lp | Monovinylarene conjugated diene copolymer compositions for acrylate blends |
| CN103073831B (zh) * | 2010-12-30 | 2016-02-10 | 中国石油化工股份有限公司 | 一种嵌段共聚物、其制备方法及其用途 |
| EP2679626B1 (en) * | 2011-02-23 | 2016-06-08 | Bridgestone Corporation | Rubber composition and tire produced using same, and process of producing rubber composition |
-
2014
- 2014-07-07 JP JP2016524769A patent/JP6594305B2/ja not_active Expired - Fee Related
- 2014-07-07 WO PCT/EP2014/064411 patent/WO2015004043A1/en not_active Ceased
- 2014-07-07 EP EP14735589.5A patent/EP3019542B1/en not_active Not-in-force
- 2014-07-07 US US14/903,505 patent/US9845374B2/en not_active Expired - Fee Related
- 2014-07-07 CN CN201480038855.1A patent/CN105377924B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US9845374B2 (en) | 2017-12-19 |
| EP3019542B1 (en) | 2017-07-05 |
| EP3019542A1 (en) | 2016-05-18 |
| CN105377924B (zh) | 2018-08-10 |
| JP2016524027A (ja) | 2016-08-12 |
| CN105377924A (zh) | 2016-03-02 |
| US20160168303A1 (en) | 2016-06-16 |
| WO2015004043A1 (en) | 2015-01-15 |
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