JP6279588B2 - ポリベンゾオキサジン組成物 - Google Patents
ポリベンゾオキサジン組成物 Download PDFInfo
- Publication number
- JP6279588B2 JP6279588B2 JP2015534588A JP2015534588A JP6279588B2 JP 6279588 B2 JP6279588 B2 JP 6279588B2 JP 2015534588 A JP2015534588 A JP 2015534588A JP 2015534588 A JP2015534588 A JP 2015534588A JP 6279588 B2 JP6279588 B2 JP 6279588B2
- Authority
- JP
- Japan
- Prior art keywords
- benzoxazine
- polymerizable composition
- group
- composition
- 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 - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims description 171
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 claims description 96
- 229920000642 polymer Polymers 0.000 claims description 59
- 125000005842 heteroatom Chemical group 0.000 claims description 45
- 239000003054 catalyst Substances 0.000 claims description 43
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 42
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 29
- 229920000647 polyepoxide Polymers 0.000 claims description 22
- 239000012745 toughening agent Substances 0.000 claims description 22
- 150000001412 amines Chemical class 0.000 claims description 20
- 150000005130 benzoxazines Chemical group 0.000 claims description 19
- 125000001931 aliphatic group Chemical group 0.000 claims description 17
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 15
- 239000003822 epoxy resin Substances 0.000 claims description 14
- 239000003085 diluting agent Substances 0.000 claims description 13
- 238000006116 polymerization reaction Methods 0.000 claims description 13
- 150000004985 diamines Chemical class 0.000 claims description 12
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 10
- 150000004982 aromatic amines Chemical class 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 229960005265 selenium sulfide Drugs 0.000 claims description 4
- JNMWHTHYDQTDQZ-UHFFFAOYSA-N selenium sulfide Chemical compound S=[Se]=S JNMWHTHYDQTDQZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 claims 1
- VIDTVPHHDGRGAF-UHFFFAOYSA-N selenium sulfide Chemical compound [Se]=S VIDTVPHHDGRGAF-UHFFFAOYSA-N 0.000 claims 1
- -1 benzoxazine compound Chemical class 0.000 description 80
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- 238000005481 NMR spectroscopy Methods 0.000 description 13
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
- 150000003573 thiols Chemical class 0.000 description 12
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- 125000000524 functional group Chemical group 0.000 description 11
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- 125000003277 amino group Chemical group 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 8
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
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- 239000000376 reactant Substances 0.000 description 7
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical group N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
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- 239000007795 chemical reaction product Substances 0.000 description 6
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- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
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- 239000002313 adhesive film Substances 0.000 description 5
- 239000002671 adjuvant Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
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- 238000000113 differential scanning calorimetry Methods 0.000 description 5
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
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- 235000013824 polyphenols Nutrition 0.000 description 5
- 229910052711 selenium Inorganic materials 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
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- 239000004416 thermosoftening plastic Substances 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- 229920002799 BoPET Polymers 0.000 description 4
- 229920000459 Nitrile rubber Polymers 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Chemical group 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
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- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
- C08K5/357—Six-membered rings
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Sealing Material Composition (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (3)
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| US201261706808P | 2012-09-28 | 2012-09-28 | |
| US61/706,808 | 2012-09-28 | ||
| PCT/US2013/061273 WO2014052255A1 (en) | 2012-09-28 | 2013-09-24 | Polybenzoxazine composition |
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| CN (1) | CN104781308B (enExample) |
| WO (1) | WO2014052255A1 (enExample) |
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| US10920020B2 (en) | 2011-08-11 | 2021-02-16 | Arizona Board Of Regents On Behalf Of The University Of Arizona | 3D-printing of ultra-high refractive index polymers |
| US11015023B2 (en) | 2011-08-11 | 2021-05-25 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Fire retardant compositions utilizing elemental sulfur |
| US9567439B1 (en) | 2011-08-11 | 2017-02-14 | The Arizona Board Of Regents On Behalf Of The University Of Arizona | Sulfur composites and polymeric materials from elemental sulfur |
| US11795248B2 (en) | 2011-08-11 | 2023-10-24 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Copolymerization of elemental sulfur and epoxy functional styrenics |
| EP2938652B1 (en) | 2012-12-27 | 2021-03-31 | 3M Innovative Properties Company | Polymerizable composition including a benzoxazine and an acid-forming peroxide catalyst, article, and method |
| KR20160003641A (ko) | 2013-04-30 | 2016-01-11 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 폴리(벤족사진)의 제조 방법 |
| WO2015057414A1 (en) | 2013-10-16 | 2015-04-23 | 3M Innovative Properties Company | Benzoxazine polymerization |
| US10894863B2 (en) | 2014-02-14 | 2021-01-19 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Cathode materials for Li—S batteries |
| JP2017517603A (ja) * | 2014-02-14 | 2017-06-29 | ザ アリゾナ ボード オブ リージェンツ オン ビハーフ オブ ザ ユニバーシティー オブ アリゾナThe Arizona Board of Regents on behalf of The University of Arizona | 元素状硫黄に由来する硫黄複合材及び重合体材料 |
| JP2017538836A (ja) * | 2014-12-18 | 2017-12-28 | スリーエム イノベイティブ プロパティズ カンパニー | 改善された熱安定性を有する硬化性ベンゾオキサジン組成物 |
| US20160297994A1 (en) * | 2015-04-10 | 2016-10-13 | Eastman Chemical Company | Curable benzoxazine-based phenolic resins and coating compositions thereof |
| KR102272186B1 (ko) | 2015-06-16 | 2021-07-02 | 코오롱인더스트리 주식회사 | 주쇄 벤족사진을 포함하는 고무 조성물 및 그 제조방법 |
| US11078333B2 (en) | 2015-07-13 | 2021-08-03 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Copolymerization of elemental sulfur to synthesize high sulfur content polymeric materials |
| MX2018013703A (es) | 2016-05-10 | 2019-05-02 | Huntsman Advanced Mat Americas Llc | Benzotiazoles como catalizadores latentes para resinas de benzoxazina. |
| WO2017200180A1 (ko) * | 2016-05-17 | 2017-11-23 | 주식회사 엘지화학 | 고분자-황 공중합체, 이의 제조방법 및 이를 포함하는 리튬-황 전지 |
| KR102006724B1 (ko) | 2016-05-17 | 2019-08-02 | 주식회사 엘지화학 | 고분자-황 공중합체, 이의 제조방법 및 이를 포함하는 리튬-황 전지 |
| US10731003B2 (en) | 2016-09-15 | 2020-08-04 | 3M Innovative Properties Company | Benzoxazine composition |
| FR3057802A1 (fr) * | 2016-10-26 | 2018-04-27 | Compagnie Generale Des Etablissements Michelin | Renfort metallique ou metallise dont la surface est revetue d'une polybenzoxazine |
| US11649548B2 (en) | 2016-12-09 | 2023-05-16 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Metallopolymers for catalytic generation of hydrogen |
| WO2018232155A1 (en) | 2017-06-15 | 2018-12-20 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Chalcogenide hybrid inorganic/organic polymer (chip) materials as improved crosslinking agents for vulcanization |
| CA3082116A1 (en) | 2017-12-14 | 2019-06-20 | Sara DE VRIJ | Pressure sensitive adhesive with broad damping temperature and frequency range |
| IL260726B (en) | 2018-07-22 | 2021-09-30 | D Fend Solutions Ad Ltd | Interfering in time-division duplex communication |
| WO2020169785A1 (en) | 2019-02-22 | 2020-08-27 | Universitat Autonoma De Barcelona | Process for polymerizing 1,3-benzoxazines |
| US11396581B2 (en) * | 2020-05-08 | 2022-07-26 | Baker Hughes Oilfield Operations Llc | Oxyalkylated polybenzoxazine emulsion breakers |
| US11162036B1 (en) * | 2020-05-13 | 2021-11-02 | Baker Hughes Oilfield Operations Llc | Polybenzoxazine asphaltene inhibitors |
| CN112778519B (zh) * | 2020-12-30 | 2022-04-15 | 山东大学 | 含官能团的苯并噁嗪齐聚物、高耐热固化物及其制备方法 |
| EP4613790A1 (en) * | 2024-03-05 | 2025-09-10 | Empa | High performance sulphur-enriched polymers and composites thereof |
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| US3496250A (en) | 1967-02-21 | 1970-02-17 | Borg Warner | Blends of epoxy resins and acrylonitrile butadiene-styrene graft copolymers |
| US3890272A (en) | 1973-05-25 | 1975-06-17 | Univ Notre Dame Du Lac | Polymerizing bis-maleimides |
| EP0493310A1 (de) * | 1990-12-21 | 1992-07-01 | Gurit-Essex AG | Zu schwerentflammbaren Kunststoffen härtbare Harzmischungen und deren Verwendung |
| US5543516A (en) | 1994-05-18 | 1996-08-06 | Edison Polymer Innovation Corporation | Process for preparation of benzoxazine compounds in solventless systems |
| CN1059909C (zh) * | 1995-06-23 | 2000-12-27 | 四川联合大学 | 粒状多苯并嗪中间体及其制备方法 |
| US6207586B1 (en) | 1998-10-28 | 2001-03-27 | Lucent Technologies Inc. | Oxide/nitride stacked gate dielectric and associated methods |
| US6207786B1 (en) | 1998-11-10 | 2001-03-27 | Edison Polymer Innovation Corporation | Ternary systems of benzoxazine, epoxy, and phenolic resins |
| US6376080B1 (en) | 1999-06-07 | 2002-04-23 | Loctite Corporation | Method for preparing polybenzoxazine |
| ES2233564T3 (es) | 2001-01-22 | 2005-06-16 | Huntsman Advanced Materials (Switzerland) Gmbh | Agentes incombustibles. |
| MY138485A (en) | 2001-03-12 | 2009-06-30 | Hitachi Chemical Co Ltd | Process for producing benzoxazine resin |
| US6743852B2 (en) | 2001-11-13 | 2004-06-01 | Henkel Corporation | Benzoxazines, thermosetting resins comprised thereof, and methods for use thereof |
| US20100016504A1 (en) * | 2006-09-21 | 2010-01-21 | Henkel Ag & Co. Kgaa | Catalytic low temperature polymerization |
| WO2009115488A1 (en) * | 2008-03-19 | 2009-09-24 | Henkel Ag & Co. Kgaa | Copolymerization method |
| KR20110039339A (ko) * | 2008-08-14 | 2011-04-15 | 헨켈 아게 운트 코. 카게아아 | 중합성 벤족사진 조성물 |
| US8389758B2 (en) * | 2009-06-05 | 2013-03-05 | 3M Innovative Properties Company | Benzoxazine-thiol adducts |
| US8383706B2 (en) | 2009-06-05 | 2013-02-26 | 3M Innovative Properties Company | Benzoxazine-thiol adducts |
| US20110054100A1 (en) * | 2009-08-26 | 2011-03-03 | 3M Innovative Properties Company | Polybenzoxazine composition |
| CN102575062B (zh) * | 2009-10-22 | 2014-12-24 | 汉高股份有限及两合公司 | 含苯并噁嗪化合物和作为可热活化的催化剂的具有环结构的磺酸酯的可固化的组合物 |
| US9840591B2 (en) * | 2010-08-04 | 2017-12-12 | 3M Innovative Properties Company | Method of preparing benzoxazine-thiol polymers films |
| CN102161762A (zh) * | 2011-01-19 | 2011-08-24 | 华东理工大学 | 一种改性苯并噁嗪树脂的方法 |
| EP2487215B1 (en) * | 2011-02-11 | 2013-07-24 | Henkel AG & Co. KGaA | Electrically conductive adhesives comprising at least one metal precursor |
| CN103562317A (zh) | 2011-03-28 | 2014-02-05 | 3M创新有限公司 | 可固化组合物、制品、固化方法和反应产物 |
| JP6109144B2 (ja) | 2011-03-28 | 2017-04-05 | スリーエム イノベイティブ プロパティズ カンパニー | 硬化性組成物、物品、硬化方法及びタックフリー反応生成物 |
| KR101993864B1 (ko) | 2011-09-28 | 2019-06-27 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 벤족사진의 아민/티올 경화 |
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| WO2014052255A1 (en) | 2014-04-03 |
| US20150218429A1 (en) | 2015-08-06 |
| EP2900731A1 (en) | 2015-08-05 |
| JP2015530462A (ja) | 2015-10-15 |
| CN104781308B (zh) | 2016-12-21 |
| CN104781308A (zh) | 2015-07-15 |
| EP2900731B1 (en) | 2018-09-05 |
| US9416302B2 (en) | 2016-08-16 |
| KR20150065751A (ko) | 2015-06-15 |
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