ES2562106T3 - Composiciones de resina termoestable con mayor resistencia - Google Patents
Composiciones de resina termoestable con mayor resistencia Download PDFInfo
- Publication number
- ES2562106T3 ES2562106T3 ES12756801.2T ES12756801T ES2562106T3 ES 2562106 T3 ES2562106 T3 ES 2562106T3 ES 12756801 T ES12756801 T ES 12756801T ES 2562106 T3 ES2562106 T3 ES 2562106T3
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- Prior art keywords
- polymer
- thermosetting resin
- low
- aromatic
- resin
- Prior art date
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- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 87
- 239000011342 resin composition Substances 0.000 title claims description 23
- 229920000642 polymer Polymers 0.000 claims abstract description 222
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- 239000011347 resin Substances 0.000 claims abstract description 144
- 239000000203 mixture Substances 0.000 claims abstract description 130
- 229920001400 block copolymer Polymers 0.000 claims abstract description 80
- 239000002243 precursor Substances 0.000 claims abstract description 68
- 125000003118 aryl group Chemical group 0.000 claims abstract description 61
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 39
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 19
- 230000009477 glass transition Effects 0.000 claims abstract description 19
- -1 aliphatic alcohols Chemical class 0.000 claims abstract description 17
- 239000000126 substance Substances 0.000 claims abstract description 16
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 15
- 150000001298 alcohols Chemical class 0.000 claims abstract description 14
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 14
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 14
- 230000003252 repetitive effect Effects 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 13
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 12
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 9
- 150000003568 thioethers Chemical class 0.000 claims abstract description 6
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- 229920000647 polyepoxide Polymers 0.000 claims description 54
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 12
- 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 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 8
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- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 8
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- 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 6
- 238000007306 functionalization reaction Methods 0.000 claims description 6
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- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
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- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- DEQUKPCANKRTPZ-UHFFFAOYSA-N (2,3-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1O DEQUKPCANKRTPZ-UHFFFAOYSA-N 0.000 claims description 3
- FAUAZXVRLVIARB-UHFFFAOYSA-N 4-[[4-[bis(oxiran-2-ylmethyl)amino]phenyl]methyl]-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC(CC=2C=CC(=CC=2)N(CC2OC2)CC2OC2)=CC=1)CC1CO1 FAUAZXVRLVIARB-UHFFFAOYSA-N 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
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- 238000005304 joining Methods 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 2
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 claims description 2
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- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 claims description 2
- 150000001718 carbodiimides Chemical class 0.000 claims description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 2
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- 150000005846 sugar alcohols Polymers 0.000 claims description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims 1
- 150000007824 aliphatic compounds Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 41
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
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- 229920006393 polyether sulfone Polymers 0.000 description 28
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- 239000002245 particle Substances 0.000 description 25
- 239000003607 modifier Substances 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 17
- 239000004593 Epoxy Substances 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 16
- 239000003054 catalyst Substances 0.000 description 13
- 239000012046 mixed solvent Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 101000605126 Mus musculus Prostaglandin G/H synthase 2 Proteins 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
- 238000001723 curing Methods 0.000 description 10
- 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 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
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- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 7
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 6
- 239000002086 nanomaterial Substances 0.000 description 6
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- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 6
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 5
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 5
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- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 4
- 150000001263 acyl chlorides Chemical class 0.000 description 4
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- C08G59/20—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 epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/38—Epoxy compounds containing three or more epoxy groups together with di-epoxy compounds
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| GBGB1113196.8A GB201113196D0 (en) | 2011-08-01 | 2011-08-01 | Thermoset resin compositions with increased toughness |
| GB201113196 | 2011-08-01 | ||
| PCT/GB2012/051779 WO2013017843A2 (en) | 2011-08-01 | 2012-07-25 | Thermoset resin compositions with increased toughness |
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| ES2562106T3 true ES2562106T3 (es) | 2016-03-02 |
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Family Applications (1)
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| ES12756801.2T Active ES2562106T3 (es) | 2011-08-01 | 2012-07-25 | Composiciones de resina termoestable con mayor resistencia |
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| EP2808353A1 (en) * | 2013-05-31 | 2014-12-03 | Huntsman International Llc | A method for improving toughness of polyisocyanate polyaddition reaction products |
| JP5852633B2 (ja) * | 2013-07-04 | 2016-02-03 | 太陽インキ製造株式会社 | 硬化性樹脂組成物、その硬化物、これを有するプリント配線板、及び硬化物の製造方法 |
| JP2017523256A (ja) | 2014-05-22 | 2017-08-17 | サイテック インダストリーズ インコーポレイテッド | 強化剤として使用するための官能化重合体粒子 |
| US10023735B2 (en) | 2014-08-18 | 2018-07-17 | International Business Machines Corporation | 3D printing with PHT/PHA based materials and polymerizable monomers |
| US9957345B2 (en) | 2014-08-18 | 2018-05-01 | International Business Machines Corporation | 3D printing with PHT based materials |
| KR102408039B1 (ko) * | 2014-12-18 | 2022-06-13 | 사이텍 인더스트리스 인코포레이티드 | 액상 수지 주입에 적합한 개질된 수지 시스템 |
| US20190023863A1 (en) * | 2015-07-30 | 2019-01-24 | University Of Massachusetts | Impact modified compositions methods of manufacture thereof and articles comprising the same |
| US9758620B2 (en) | 2015-09-03 | 2017-09-12 | International Business Machines Corporation | Tailorable viscoelastic properties of PEG-hemiaminal organogel networks |
| KR101720563B1 (ko) * | 2015-11-05 | 2017-03-29 | 국방과학연구소 | 폴리술폰계 고분자 강인화제를 함유하는 폴리술폰계 고분자 강인화 에폭시 수지 조성물 및 이의 제조 방법 |
| US9873766B2 (en) | 2015-11-24 | 2018-01-23 | International Business Machines Corporation | Systems chemistry approach to polyhexahydrotriazine polymeric structures |
| US10968367B2 (en) | 2016-11-08 | 2021-04-06 | H.B. Fuller Company | Low temperature curable adhesive composition and articles including the same |
| JPWO2018131580A1 (ja) * | 2017-01-13 | 2019-11-07 | 東レ株式会社 | エポキシ樹脂組成物、エポキシ樹脂硬化物、プリプレグ、繊維強化複合材料、ブロック共重合体およびその製造方法 |
| US10213642B2 (en) * | 2017-04-28 | 2019-02-26 | Katie Swarts | Terrain belt for use with a treadmill |
| CN110914355A (zh) * | 2017-07-12 | 2020-03-24 | 赫克塞尔合成有限公司 | 树脂组合物 |
| KR102802243B1 (ko) * | 2018-03-16 | 2025-05-07 | 훈츠만 어드밴스트 머티리얼스 라이센싱 (스위처랜드) 게엠베하 | 저장 안정성 조성물 및 경화성 수지 조성물 |
| KR102311641B1 (ko) | 2018-11-23 | 2021-10-13 | 주식회사 엘지화학 | 수지 조성물, 이를 포함하는 프리프레그, 이를 포함하는 적층판, 및 이를 포함하는 수지 부착 금속박 |
| US11086200B2 (en) | 2019-03-20 | 2021-08-10 | Ticona Llc | Polymer composition for use in a camera module |
| CN113710738A (zh) * | 2019-03-20 | 2021-11-26 | 提克纳有限责任公司 | 用于相机模块的致动器组件 |
| KR20230146005A (ko) * | 2021-02-18 | 2023-10-18 | 도레이 카부시키가이샤 | 섬유 강화 복합 재료용 에폭시 수지 조성물, 섬유 강화복합 재료, 및 섬유 강화 복합 재료의 제조 방법 |
| US12209163B2 (en) | 2021-05-06 | 2025-01-28 | Ticona Llc | Polymer composition for use in a camera module |
| DE102021121497A1 (de) | 2021-08-19 | 2023-02-23 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein | Zusammensetzung zur Herstellung eines flächigen Halbzeugs |
| TW202340697A (zh) | 2021-12-13 | 2023-10-16 | 美商堤康那責任有限公司 | 樣品之滾珠凹部性質之測試技術 |
| JP7541419B2 (ja) | 2022-04-22 | 2024-08-28 | エル・コーポレイション | アクリレート官能基を有する線状ブロック共重合体強化剤 |
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2011
- 2011-08-01 GB GBGB1113196.8A patent/GB201113196D0/en not_active Ceased
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- 2012-06-21 TW TW101122289A patent/TWI548698B/zh not_active IP Right Cessation
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- 2012-07-25 IN IN768CHN2014 patent/IN2014CN00768A/en unknown
- 2012-07-25 KR KR1020147005303A patent/KR102000655B1/ko not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| TWI548698B (zh) | 2016-09-11 |
| KR20140063647A (ko) | 2014-05-27 |
| KR102000655B1 (ko) | 2019-07-16 |
| TW201307479A (zh) | 2013-02-16 |
| MX2014001309A (es) | 2014-04-14 |
| US8907049B2 (en) | 2014-12-09 |
| JP6184951B2 (ja) | 2017-08-23 |
| EP2739672A2 (en) | 2014-06-11 |
| GB201113196D0 (en) | 2011-09-14 |
| MX343157B (es) | 2016-10-26 |
| WO2013017843A2 (en) | 2013-02-07 |
| CN103906793B (zh) | 2016-04-27 |
| RU2611628C2 (ru) | 2017-02-28 |
| JP2014521800A (ja) | 2014-08-28 |
| IN2014CN00768A (enExample) | 2015-04-03 |
| AU2012291863A1 (en) | 2014-01-23 |
| CA2843659A1 (en) | 2013-02-07 |
| EP2739672B1 (en) | 2015-11-18 |
| BR112014002564B1 (pt) | 2021-04-06 |
| BR112014002564A2 (pt) | 2017-02-21 |
| US20130184376A1 (en) | 2013-07-18 |
| WO2013017843A3 (en) | 2013-06-13 |
| CN103906793A (zh) | 2014-07-02 |
| RU2014107837A (ru) | 2015-09-10 |
| CA2843659C (en) | 2020-01-14 |
| MY171025A (en) | 2019-09-23 |
| AU2012291863B2 (en) | 2015-06-25 |
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