JP5484464B2 - 重合性組成物 - Google Patents
重合性組成物 Download PDFInfo
- Publication number
- JP5484464B2 JP5484464B2 JP2011522512A JP2011522512A JP5484464B2 JP 5484464 B2 JP5484464 B2 JP 5484464B2 JP 2011522512 A JP2011522512 A JP 2011522512A JP 2011522512 A JP2011522512 A JP 2011522512A JP 5484464 B2 JP5484464 B2 JP 5484464B2
- Authority
- JP
- Japan
- Prior art keywords
- polymerizable composition
- benzoxazine
- formula
- nitrogen
- hydrogen
- 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 123
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 claims description 67
- 125000002947 alkylene group Chemical group 0.000 claims description 46
- -1 benzoxazine compound Chemical class 0.000 claims description 45
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 36
- 150000005130 benzoxazines Chemical class 0.000 claims description 34
- 229910052760 oxygen Inorganic materials 0.000 claims description 32
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- 239000001301 oxygen Substances 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
- 229910052717 sulfur Inorganic materials 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 23
- 239000000835 fiber Substances 0.000 claims description 23
- 239000011593 sulfur Substances 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 238000006116 polymerization reaction Methods 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 19
- 229940126062 Compound A Drugs 0.000 claims description 16
- 239000004593 Epoxy Substances 0.000 claims description 16
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- QEQVCPKISCKMOQ-UHFFFAOYSA-N 3h-benzo[f][1,2]benzoxazine Chemical group C1=CC=CC2=C(C=CNO3)C3=CC=C21 QEQVCPKISCKMOQ-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
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- 150000003457 sulfones Chemical class 0.000 claims description 9
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 5
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims description 4
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- 238000005304 joining Methods 0.000 claims description 2
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- 238000006243 chemical reaction Methods 0.000 description 23
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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 13
- 229910052799 carbon Inorganic materials 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
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- 239000003054 catalyst Substances 0.000 description 9
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- 229920002866 paraformaldehyde Polymers 0.000 description 8
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 7
- 150000002989 phenols Chemical class 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 101000901617 Notophthalmus viridescens Homeobox protein DLX-3 Proteins 0.000 description 5
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- 238000000576 coating method Methods 0.000 description 5
- 239000003822 epoxy resin Substances 0.000 description 5
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- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- 125000006413 ring segment Chemical group 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 241001598984 Bromius obscurus Species 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 4
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- 125000004429 atom Chemical group 0.000 description 4
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- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- BLDLRWQLBOJPEB-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfanylphenol Chemical compound OC1=CC=CC=C1SC1=CC=CC=C1O BLDLRWQLBOJPEB-UHFFFAOYSA-N 0.000 description 3
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 3
- 0 CC**1COC(C=CC)=C(C)C1 Chemical compound CC**1COC(C=CC)=C(C)C1 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
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- 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 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 125000003504 2-oxazolinyl group Chemical class O1C(=NCC1)* 0.000 description 2
- KDHWOCLBMVSZPG-UHFFFAOYSA-N 3-imidazol-1-ylpropan-1-amine Chemical compound NCCCN1C=CN=C1 KDHWOCLBMVSZPG-UHFFFAOYSA-N 0.000 description 2
- 229920003319 Araldite® Polymers 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
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- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 230000036314 physical performance Effects 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
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- 238000010189 synthetic method Methods 0.000 description 1
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- YOIAWAIKYVEKMF-UHFFFAOYSA-N trifluoromethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)F.OS(=O)(=O)C(F)(F)F YOIAWAIKYVEKMF-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/16—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with only hydrogen or carbon atoms directly attached in positions 2 and 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/249921—Web or sheet containing structurally defined element or component
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Plural Heterocyclic Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08014512 | 2008-08-14 | ||
| EP08014512.1 | 2008-08-14 | ||
| PCT/EP2009/060448 WO2010018198A1 (en) | 2008-08-14 | 2009-08-12 | Polymerizable benzoxazine compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011530570A JP2011530570A (ja) | 2011-12-22 |
| JP2011530570A5 JP2011530570A5 (https=) | 2013-05-16 |
| JP5484464B2 true JP5484464B2 (ja) | 2014-05-07 |
Family
ID=41228600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011522512A Expired - Fee Related JP5484464B2 (ja) | 2008-08-14 | 2009-08-12 | 重合性組成物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20110189458A1 (https=) |
| EP (1) | EP2323995B1 (https=) |
| JP (1) | JP5484464B2 (https=) |
| KR (1) | KR20110039339A (https=) |
| CN (1) | CN102119154A (https=) |
| WO (1) | WO2010018198A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US8288591B2 (en) | 2008-11-20 | 2012-10-16 | Designer Molecules, Inc. | Curing agents for epoxy resins |
| DE102009028099A1 (de) * | 2009-07-29 | 2011-02-03 | Henkel Ag & Co. Kgaa | Schlagzähmodifizierte Zusammensetzungen |
| WO2011116050A2 (en) * | 2010-03-17 | 2011-09-22 | Designer Molecules, Inc. | Curing agents for epoxy resins |
| CN105108929B (zh) * | 2010-04-13 | 2021-06-22 | 汉高知识产权控股有限责任公司 | 可固化的组合物、利用该组合物制备复合材料的方法以及制备表面光洁度优异且纤维固结高的复合材料的方法 |
| US9178237B2 (en) | 2010-12-14 | 2015-11-03 | Samsung Electronics Co., Ltd. | Conductive composition and method of preparation, polymer thereof, and electrode, electrolyte membrane and fuel cell including the composition or polymer |
| JP5923291B2 (ja) * | 2010-12-14 | 2016-05-24 | 三星電子株式会社Ｓａｍｓｕｎｇ Ｅｌｅｃｔｒｏｎｉｃｓ Ｃｏ．，Ｌｔｄ． | 伝導性作用基を有する化合物、その重合体、これを含んだ燃料電池用電極、これを含んだ燃料電池用電解質膜及びこれを採用した燃料電池 |
| US9416302B2 (en) * | 2012-09-28 | 2016-08-16 | 3M Innovative Properties Company | Polybenzoxazine composition |
| SG11201510498WA (en) * | 2013-06-21 | 2016-01-28 | Nissan Chemical Ind Ltd | Thermosetting resin composition containing polymer having specific terminal structure |
| EP3240829B1 (en) * | 2014-12-29 | 2019-08-21 | Cytec Industries Inc. | Benzoxazines and compositions containing the same |
| CN107428708B (zh) * | 2015-03-04 | 2021-11-09 | 亨斯迈先进材料美国有限责任公司 | 苯并噁嗪低温可固化组合物 |
| BR112018001264B1 (pt) * | 2015-07-23 | 2022-04-19 | Huntsman Advanced Materials Americas Llc | Composição curável, processo para produção de uma composição curável, artigo curado, e, método para produção de um prepreg ou towpreg. |
| CN106518926B (zh) * | 2016-11-09 | 2018-08-14 | 湖北大学 | 一种含dopo的水溶性苯并恶嗪化合物的制备方法 |
| KR101997349B1 (ko) * | 2017-11-03 | 2019-07-05 | 주식회사 케이씨씨 | 에폭시 수지 조성물 |
| LU102316B1 (en) * | 2020-12-09 | 2022-06-13 | Luxembourg Inst Science & Tech List | Catalysts for benzoxazine |
| CN116745271A (zh) * | 2021-01-29 | 2023-09-12 | 本州化学工业株式会社 | 苯并噁嗪化合物的新型制造方法 |
| US20240279189A1 (en) * | 2021-01-29 | 2024-08-22 | Honshu Chemical Industry Co., Ltd. | Method for producing benzoxazine compound |
| CN116724027B (zh) * | 2021-01-29 | 2026-03-06 | 本州化学工业株式会社 | 新型苯并噁嗪化合物、含有该化合物的树脂原料组合物、固化性树脂组合物及其固化物 |
| US20240101522A1 (en) * | 2021-01-29 | 2024-03-28 | Honshu Chemical Industry Co., Ltd. | Novel method for producing benzoxazine compound |
| KR20230137341A (ko) | 2021-01-29 | 2023-10-04 | 혼슈우 카가쿠고교 가부시키가이샤 | 신규한 벤즈옥사진 화합물, 그것을 함유하는 수지 원료조성물, 경화성 수지 조성물 및 그의 경화물 |
| US20250051509A1 (en) | 2021-09-10 | 2025-02-13 | Honshu Chemical Industry Co., Ltd. | Curable resin composition, varnish, cured product, and method for producing cured product |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3433851C2 (de) * | 1984-09-14 | 1987-01-08 | Gurit-Essex Ag, Freienbach | Chemisch härtbare Harze aus 1-Oxa-3-aza-tetralin-Gruppen enthaltenden Verbindungen und cycloaliphatischen Epoxid-harzen, Verfahren zu deren Herstellung sowie Verwendung solcher Harze |
| DE58909626D1 (de) * | 1988-07-18 | 1996-04-25 | Gurit Essex Ag | Zu schwerentflammbaren und hochtemperaturbeständigen Kunststoffen härtbare Harze und Verfahren zu deren Herstellung |
| US5443911A (en) * | 1990-05-21 | 1995-08-22 | Gurit-Essex Ag | Curable resins comprising halogenated epoxy resins and 1-oxa-3-aza tetraline compounds, method for preparing and use of resins |
| 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 |
| JPH111604A (ja) * | 1997-06-11 | 1999-01-06 | Hitachi Chem Co Ltd | 熱硬化性樹脂組成物 |
| US6225440B1 (en) * | 1998-06-26 | 2001-05-01 | Edison Polymer Innovation Corporation | Cationic ring-opening polymerization of benzoxazines |
| US6376080B1 (en) * | 1999-06-07 | 2002-04-23 | Loctite Corporation | Method for preparing polybenzoxazine |
| WO2001034581A1 (en) * | 1999-11-05 | 2001-05-17 | The Dow Chemical Company | High char yield benzoxazine compositions |
| US6437026B1 (en) * | 2001-01-05 | 2002-08-20 | Cookson Singapore Pte Ltd. | Hardener for epoxy molding compounds |
| US20030023007A1 (en) * | 2001-07-27 | 2003-01-30 | Hycomp, Inc. | Enhancement of thermal properties of benzoxazine polymers by use of aromatic polyamines to incorporate internal benzoxazine groups within the monomer |
| US6743852B2 (en) * | 2001-11-13 | 2004-06-01 | Henkel Corporation | Benzoxazines, thermosetting resins comprised thereof, and methods for use thereof |
| US6620905B1 (en) * | 2002-02-23 | 2003-09-16 | National Starch And Chemical Investment Holding Corporation | Curable compositions containing benzoxazine |
| US20070191555A1 (en) * | 2004-03-30 | 2007-08-16 | Hatsuo Ishida | Thermosetting resin composition and its article |
| US20060025509A1 (en) * | 2004-07-29 | 2006-02-02 | Ruzhi Zhang | Fluxing no-flow underfill composition containing benzoxazines |
| US7649060B2 (en) * | 2005-12-02 | 2010-01-19 | Henkel Corporation | Curable compositions |
| EP2218748B1 (en) * | 2005-09-03 | 2012-10-10 | Samsung SDI Co., Ltd. | Polybenzoxazine-based compound, electrolyte membrane including the same, and fuel cell employing the electrolyte membrane |
| JP2007169587A (ja) * | 2005-11-24 | 2007-07-05 | Sekisui Chem Co Ltd | 繊維複合体及びその製造方法 |
| JP2008050557A (ja) * | 2005-11-24 | 2008-03-06 | Sekisui Chem Co Ltd | 繊維複合体及びその製造方法 |
| KR100754374B1 (ko) * | 2006-02-07 | 2007-08-31 | 삼성에스디아이 주식회사 | 폴리벤조옥사진계 화합물을 이용한 전해질막 및 그제조방법 |
| KR100818255B1 (ko) * | 2006-05-29 | 2008-04-02 | 삼성에스디아이 주식회사 | 폴리벤조옥사진계 화합물, 이를 포함한 전해질막 및 이를채용한 연료전지 |
| JP5409373B2 (ja) * | 2006-11-13 | 2014-02-05 | ヘンケル コーポレイション | コア−シェルゴムを有するベンゾキサジン組成物 |
| JP2008195907A (ja) * | 2007-02-16 | 2008-08-28 | Shikoku Chem Corp | 熱硬化性ベンゾオキサジン樹脂組成物 |
-
2009
- 2009-08-12 EP EP20090781761 patent/EP2323995B1/en not_active Not-in-force
- 2009-08-12 JP JP2011522512A patent/JP5484464B2/ja not_active Expired - Fee Related
- 2009-08-12 KR KR1020117003126A patent/KR20110039339A/ko not_active Withdrawn
- 2009-08-12 WO PCT/EP2009/060448 patent/WO2010018198A1/en not_active Ceased
- 2009-08-12 CN CN2009801313246A patent/CN102119154A/zh active Pending
-
2011
- 2011-02-14 US US13/026,639 patent/US20110189458A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP2011530570A (ja) | 2011-12-22 |
| EP2323995B1 (en) | 2012-11-21 |
| WO2010018198A1 (en) | 2010-02-18 |
| US20110189458A1 (en) | 2011-08-04 |
| CN102119154A (zh) | 2011-07-06 |
| KR20110039339A (ko) | 2011-04-15 |
| EP2323995A1 (en) | 2011-05-25 |
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