JP5690851B2 - 低発熱性を有する熱可塑性樹脂強化シアネートエステル樹脂複合材 - Google Patents
低発熱性を有する熱可塑性樹脂強化シアネートエステル樹脂複合材 Download PDFInfo
- Publication number
- JP5690851B2 JP5690851B2 JP2012555012A JP2012555012A JP5690851B2 JP 5690851 B2 JP5690851 B2 JP 5690851B2 JP 2012555012 A JP2012555012 A JP 2012555012A JP 2012555012 A JP2012555012 A JP 2012555012A JP 5690851 B2 JP5690851 B2 JP 5690851B2
- Authority
- JP
- Japan
- Prior art keywords
- cyanate ester
- weight percent
- resin
- ester resin
- composite part
- 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
- 239000004643 cyanate ester Substances 0.000 title claims description 108
- 229920005992 thermoplastic resin Polymers 0.000 title description 15
- 239000000805 composite resin Substances 0.000 title description 11
- 229920005989 resin Polymers 0.000 claims description 140
- 239000011347 resin Substances 0.000 claims description 140
- 239000002131 composite material Substances 0.000 claims description 83
- 239000004697 Polyetherimide Substances 0.000 claims description 43
- 229920001601 polyetherimide Polymers 0.000 claims description 43
- 239000011159 matrix material Substances 0.000 claims description 40
- 229920002312 polyamide-imide Polymers 0.000 claims description 38
- 239000004962 Polyamide-imide Substances 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 34
- 230000002787 reinforcement Effects 0.000 claims description 22
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 19
- 229910052698 phosphorus Inorganic materials 0.000 claims description 19
- 239000011574 phosphorus Substances 0.000 claims description 19
- 239000000835 fiber Substances 0.000 claims description 18
- 239000003063 flame retardant Substances 0.000 claims description 16
- 229920001169 thermoplastic Polymers 0.000 claims description 16
- 239000004416 thermosoftening plastic Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 14
- 229930185605 Bisphenol Natural products 0.000 claims description 10
- -1 bisphenol sulfone Chemical class 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 230000020169 heat generation Effects 0.000 claims description 5
- 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 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000004848 polyfunctional curative Substances 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 2
- 238000012360 testing method Methods 0.000 description 35
- 239000011342 resin composition Substances 0.000 description 31
- 239000002245 particle Substances 0.000 description 22
- 238000001723 curing Methods 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 13
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 10
- 238000009472 formulation Methods 0.000 description 8
- 238000011417 postcuring Methods 0.000 description 8
- 239000003351 stiffener Substances 0.000 description 8
- 229920000049 Carbon (fiber) Polymers 0.000 description 7
- 239000004917 carbon fiber Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000004952 Polyamide Substances 0.000 description 6
- 239000004963 Torlon Substances 0.000 description 6
- 229920003997 Torlon® Polymers 0.000 description 6
- 229920004752 ULTEM® 1000P Polymers 0.000 description 6
- 229920002647 polyamide Polymers 0.000 description 6
- 238000002485 combustion reaction Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000010586 diagram Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 230000002411 adverse Effects 0.000 description 3
- OWEYKIWAZBBXJK-UHFFFAOYSA-N 1,1-Dichloro-2,2-bis(4-hydroxyphenyl)ethylene Chemical compound C1=CC(O)=CC=C1C(=C(Cl)Cl)C1=CC=C(O)C=C1 OWEYKIWAZBBXJK-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- AHZMUXQJTGRNHT-UHFFFAOYSA-N [4-[2-(4-cyanatophenyl)propan-2-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C)(C)C1=CC=C(OC#N)C=C1 AHZMUXQJTGRNHT-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000004760 aramid Substances 0.000 description 2
- 229920003235 aromatic polyamide Polymers 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000748 compression moulding Methods 0.000 description 2
- QUKSVRDBEZRSSW-UHFFFAOYSA-N cyanic acid 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound N#CO.OC1=CC=C(C(C(F)(F)F)(C(F)(F)F)C(C=C2)=CC=C2O)C=C1 QUKSVRDBEZRSSW-UHFFFAOYSA-N 0.000 description 2
- ZYDCNZOJNSJLMS-PHWWCQNVSA-N dicyclopentadienylbisphenolcyanateester Chemical compound C1=CC(OC#N)=CC=C1C1CC2[C@@H](C(C3)C=4C=CC(OC#N)=CC=4)C[C@@H]3C2C1 ZYDCNZOJNSJLMS-PHWWCQNVSA-N 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 238000005304 joining Methods 0.000 description 2
- 239000012778 molding material Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000012815 thermoplastic material Substances 0.000 description 2
- PVFQHGDIOXNKIC-UHFFFAOYSA-N 4-[2-[3-[2-(4-hydroxyphenyl)propan-2-yl]phenyl]propan-2-yl]phenol Chemical compound C=1C=CC(C(C)(C)C=2C=CC(O)=CC=2)=CC=1C(C)(C)C1=CC=C(O)C=C1 PVFQHGDIOXNKIC-UHFFFAOYSA-N 0.000 description 1
- 229920012266 Poly(ether sulfone) PES Polymers 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 239000002313 adhesive film Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 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 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Images
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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
- C08G73/065—Preparatory processes
- C08G73/0655—Preparatory processes from polycyanurates
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/14—Polyamide-imides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
- C08J5/243—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using carbon fibres
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/249—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs characterised by the additives used in the prepolymer mixture
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K7/00—Use of ingredients characterised by shape
- C08K7/02—Fibres or whiskers
-
- 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
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- 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
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24132—Structurally defined web or sheet [e.g., overall dimension, etc.] including grain, strips, or filamentary elements in different layers or components parallel
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Inorganic Chemistry (AREA)
- Reinforced Plastic Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/713,534 US8283408B2 (en) | 2010-02-26 | 2010-02-26 | Thermoplastic-toughened cyanate ester resin composites with low heat release properties |
| US12/713,534 | 2010-02-26 | ||
| PCT/US2011/022799 WO2011106125A1 (en) | 2010-02-26 | 2011-01-28 | Thermoplastic-toughened cyanate ester resin composites with low heat release properties |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013520552A JP2013520552A (ja) | 2013-06-06 |
| JP2013520552A5 JP2013520552A5 (enExample) | 2014-03-13 |
| JP5690851B2 true JP5690851B2 (ja) | 2015-03-25 |
Family
ID=43798532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012555012A Expired - Fee Related JP5690851B2 (ja) | 2010-02-26 | 2011-01-28 | 低発熱性を有する熱可塑性樹脂強化シアネートエステル樹脂複合材 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US8283408B2 (enExample) |
| EP (1) | EP2539391B1 (enExample) |
| JP (1) | JP5690851B2 (enExample) |
| CN (1) | CN102770482B (enExample) |
| BR (1) | BR112012021077B1 (enExample) |
| ES (1) | ES2576277T3 (enExample) |
| RU (1) | RU2561990C2 (enExample) |
| WO (1) | WO2011106125A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060292375A1 (en) * | 2005-06-28 | 2006-12-28 | Martin Cary J | Resin compositions with high thermoplatic loading |
| EP2781539A1 (en) * | 2013-03-19 | 2014-09-24 | Siemens Aktiengesellschaft | Fibre reinforced plastic composite, method of manufacturing thereof, plastic composite starting material for manufacturing the fibre reinforced plastic composite, and component of a wind turbine comprising the fibre reinforced plastic composite |
| CN104212127A (zh) * | 2014-09-10 | 2014-12-17 | 江苏恒神纤维材料有限公司 | 低温固化高温使用的模具预浸料 |
| JP6880706B2 (ja) * | 2015-12-25 | 2021-06-02 | 東レ株式会社 | 航空機用構造体 |
| JP7192202B2 (ja) * | 2017-09-20 | 2022-12-20 | 横浜ゴム株式会社 | 繊維強化複合材料用シアネートエステル樹脂組成物、プリプレグおよび繊維強化複合材料 |
| EP3842481A4 (en) | 2018-08-22 | 2022-06-08 | Toray Industries, Inc. | PREPREGNATED |
| WO2025123021A1 (en) * | 2023-12-08 | 2025-06-12 | Barrday Corporation | Epoxy resin compositions and composite materials thereof |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4692416A (en) | 1982-12-03 | 1987-09-08 | Yeshiva University | Monoclonal antibodies reactive with shared idiotypes on human antibodies to native DNA from patients with systemic lupus erythematosus |
| US4902752A (en) | 1987-10-05 | 1990-02-20 | Hi-Tek Polymers, Inc. | Polycyanate esters of polyhydric phenols blended with thermoplastic polymers |
| GB9016343D0 (en) | 1989-08-09 | 1990-09-12 | Ici Plc | Polymer composition |
| JP2965278B2 (ja) * | 1991-12-24 | 1999-10-18 | 松下電工株式会社 | 熱硬化型ポリイミド樹脂組成物と熱硬化品およびその製造方法 |
| US5548034A (en) | 1992-07-31 | 1996-08-20 | International Business Machines Corporation | Modified dicyanate ester resins having enhanced fracture toughness |
| RU2105017C1 (ru) * | 1993-05-28 | 1998-02-20 | Всероссийский научно-исследовательский институт авиационных материалов | Состав связующего для получения препрега |
| US6194495B1 (en) | 1998-03-23 | 2001-02-27 | General Electric Company | Cyanate ester based thermoset compositions |
| US6242638B1 (en) | 1999-03-12 | 2001-06-05 | Vantico Inc. | Cyanate esters having flame resistant properties |
| ES2272518T3 (es) * | 2000-08-22 | 2007-05-01 | Cytec Technology Corp. | Elemento polimerico flexible como agente endurecedor en preipregnaciones. |
| JP2003128765A (ja) * | 2001-10-17 | 2003-05-08 | Sumitomo Bakelite Co Ltd | 耐熱性樹脂組成物、これを用いたプリプレグ及び積層板 |
| JP2003128785A (ja) | 2001-10-19 | 2003-05-08 | Hitachi Chem Co Ltd | 難燃性熱硬化性樹脂組成物並びに該組成物を用いたプリプレグ、積層板、樹脂フィルム、樹脂付き金属箔及び多層配線板とその製造方法 |
| US7087707B2 (en) | 2003-12-15 | 2006-08-08 | The United States Of America As Represented By The Secretary Of The Navy | Synthesis of oligomeric cyanate esters |
| US20050182203A1 (en) | 2004-02-18 | 2005-08-18 | Yuuichi Sugano | Novel cyanate ester compound, flame-retardant resin composition, and cured product thereof |
| GB0805640D0 (en) * | 2008-03-28 | 2008-04-30 | Hexcel Composites Ltd | Improved composite materials |
| US8034453B2 (en) | 2008-10-07 | 2011-10-11 | Hexcel Corporation | Composite materials with improved burn properties |
-
2010
- 2010-02-26 US US12/713,534 patent/US8283408B2/en active Active
-
2011
- 2011-01-28 RU RU2012140973/05A patent/RU2561990C2/ru active
- 2011-01-28 ES ES11703098.1T patent/ES2576277T3/es active Active
- 2011-01-28 JP JP2012555012A patent/JP5690851B2/ja not_active Expired - Fee Related
- 2011-01-28 BR BR112012021077-7A patent/BR112012021077B1/pt not_active IP Right Cessation
- 2011-01-28 WO PCT/US2011/022799 patent/WO2011106125A1/en not_active Ceased
- 2011-01-28 EP EP11703098.1A patent/EP2539391B1/en active Active
- 2011-01-28 CN CN201180010981.2A patent/CN102770482B/zh not_active Expired - Fee Related
-
2012
- 2012-09-12 US US13/611,812 patent/US8404777B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN102770482A (zh) | 2012-11-07 |
| CN102770482B (zh) | 2015-09-02 |
| JP2013520552A (ja) | 2013-06-06 |
| US8404777B2 (en) | 2013-03-26 |
| EP2539391A1 (en) | 2013-01-02 |
| RU2012140973A (ru) | 2014-04-10 |
| US20110212292A1 (en) | 2011-09-01 |
| EP2539391B1 (en) | 2016-03-23 |
| WO2011106125A1 (en) | 2011-09-01 |
| US20130005898A1 (en) | 2013-01-03 |
| RU2561990C2 (ru) | 2015-09-10 |
| BR112012021077B1 (pt) | 2020-06-23 |
| ES2576277T3 (es) | 2016-07-06 |
| BR112012021077A2 (pt) | 2016-05-17 |
| US8283408B2 (en) | 2012-10-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5690851B2 (ja) | 低発熱性を有する熱可塑性樹脂強化シアネートエステル樹脂複合材 | |
| US8034453B2 (en) | Composite materials with improved burn properties | |
| US10208176B2 (en) | Composite material with thermoplastic toughened novolac-based epoxy resin matrix | |
| US8404339B2 (en) | Prepreg containing epoxy resin with improved flexural properties | |
| JP7592651B2 (ja) | ハイブリッドポリアミド粒子で強化されたマトリックス樹脂 | |
| US10465052B2 (en) | Composite material with thermoplastic toughened novolac-based epoxy resin matrix | |
| AU2019215293A1 (en) | Prepreg for use in making composite parts which tolerate hot and wet conditions | |
| CN106170504A (zh) | 延长的室温储存环氧树脂 | |
| US8039109B2 (en) | Epoxy resins with improved burn properties | |
| US10787997B1 (en) | Rocket booster casings made with semipreg having a thermoplastic toughened novolac-based epoxy resin matrix | |
| JP7348181B2 (ja) | 熱可塑性強化ノボラック系エポキシ樹脂マトリックスを備えたセミプレグ |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140121 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20140121 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20140424 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140502 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140804 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20150127 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20150202 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5690851 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |