ES2612236T3 - Resinas epoxídicas con alta estabilidad y tenacidad - Google Patents
Resinas epoxídicas con alta estabilidad y tenacidad Download PDFInfo
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- ES2612236T3 ES2612236T3 ES12785700.1T ES12785700T ES2612236T3 ES 2612236 T3 ES2612236 T3 ES 2612236T3 ES 12785700 T ES12785700 T ES 12785700T ES 2612236 T3 ES2612236 T3 ES 2612236T3
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- epoxy resin
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- 229920000647 polyepoxide Polymers 0.000 title abstract description 15
- 239000003822 epoxy resin Substances 0.000 title abstract 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 title 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 14
- 239000000203 mixture Substances 0.000 abstract description 14
- 229920005989 resin Polymers 0.000 abstract description 10
- 239000011347 resin Substances 0.000 abstract description 10
- -1 bisphenol compound Chemical class 0.000 abstract description 5
- 125000003118 aryl group Chemical group 0.000 abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- 239000001257 hydrogen Substances 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 2
- 125000000962 organic group Chemical group 0.000 abstract description 2
- 229930185605 Bisphenol Natural products 0.000 abstract 1
- 239000004593 Epoxy Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000000758 substrate Substances 0.000 description 7
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- DNDWXJDUTDZBNV-UHFFFAOYSA-N 1-benzofuran-2,3-diol Chemical compound C1=CC=C2C(O)=C(O)OC2=C1 DNDWXJDUTDZBNV-UHFFFAOYSA-N 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 238000003475 lamination Methods 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical group C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 2
- 239000002648 laminated material Substances 0.000 description 2
- 239000004970 Chain extender Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000012783 reinforcing fiber Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- 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
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
- C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
- C08G59/066—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols with chain extension or advancing agents
-
- 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
- C08G59/182—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 using pre-adducts of epoxy compounds with curing agents
-
- 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
- C08G59/20—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
- C08G59/22—Di-epoxy compounds
- C08G59/226—Mixtures of di-epoxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- 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
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
-
- 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
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
- C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
-
- 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
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
- C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
- C08G59/063—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols with epihalohydrins
-
- 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
- C08G59/20—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
- C08G59/22—Di-epoxy 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
- 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
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Reinforced Plastic Materials (AREA)
Abstract
Composición de resina epoxídica que comprende: (a) una resina de poliepóxido; (b) un agente de extensión de cadena que comprende al menos un compuesto de fórmula general (III) o (V): OH-A-OH (III) R2O-A-OR2 (V) en las que A es un grupo que tiene la fórmula (IV)**Fórmula** en la que Z es hidrógeno, metilo o fenilo; y A1 representa un grupo orgánico requerido para completar un residuo aromático y R2 es un grupo alquilo funcionalizado con epoxi que tiene de 1 a 6 átomos de carbono; (c) un agente de aumento de la tenacidad; (d) un agente de curado; y opcionalmente (e) un compuesto de bisfenol.
Description
La composición de resina epoxídica también contiene un agente de extensión de cadena. El agente de extensión de 10 cadena de la presente divulgación incluye un compuesto de fórmula general (III):
OH-A-OH (III)
en la que A es un grupo que tiene la fórmula (IV) 15
en la que Z es hidrógeno, metilo o fenilo; y A1 representa un grupo orgánico requerido para completar un residuo aromático.
20 Los residuos aromáticos completados por A1; es decir residuos aromáticos formados por A1 junto con los átomos de carbono unidos indicados en la fórmula (IV), incluyen fenilo, difenilmetano (es decir, fenilmetilfenilo), bifenilo (es decir, bifenililo), difenilmetano sustituido en el grupo metano (es decir, en el átomo de carbono del metano) con uno o dos grupos alquilo C1 -C4 (es decir, fenildi(alquil C1 -C4)metilfenilo), difenilcetona (es decir, benzoilfenilo) o
25 difenilsulfona (es decir, fenilsulfonilfenilo). En algunas realizaciones, A es un grupo que tiene la fórmula:
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En una realización, la resina de poliepóxido, el componente de benzofurano-diol y/o el componente de diepóxido de benzofurano y el agente de aumento de la tenacidad se combinan con un agente de curado adecuado y son útiles como resinas de matriz de material compuesto. Pueden prepararse productos preimpregnados (prepregs) mediante la inmersión de una cinta de fibras de refuerzo continuas en una disolución de la resina (en forma monomérica o polimérica) y luego el devanado de esto sobre un tambor para formar una lámina de preimpregnación unidireccional de longitud igual a la circunferencia del tambor. También podrían usarse otros métodos de preimpregnación bien conocidos por los expertos en la técnica, tales como métodos de fusión en caliente. Entonces se evapora el disolvente del producto preimpregnado sobre el tambor o en un horno. La lámina de preimpregnación parcial o completamente secada se corta entonces en trozos más pequeños que se apilan en la configuración deseada y luego se consolidan para dar un material laminado mediante la aplicación de calor y presión. El procedimiento de laminación también sirve para curar la resina. Normalmente, el material laminado se consolida (se funde y se hace que esté libre de huecos) a una temperatura por debajo de la cual el curado es rápido. Una vez consolidado, se eleva la temperatura para realizar el curado. Después de la laminación, la pieza a menudo se cura posteriormente de manera independiente a una temperatura todavía mayor en un horno.
Las composiciones de resina epoxídica novedosas de la presente divulgación también son útiles como adhesivos de alta temperatura. Normalmente, la composición de resina puede aplicarse a cualquiera o a ambas superficies adheridas como un producto preimpregnado de tejido de vidrio, una disolución de resina (en forma monomérica o polimérica) o una película de resina. Entonces se consolida el conjunto y se cura con calor y presión de manera similar a la usada para formar los materiales compuestos descritos anteriormente.
Además, existen numerosos usos para las composiciones de resina epoxídica de la presente divulgación, tales como en aplicaciones de electrónica. Por ejemplo, pueden aplicarse desde disoluciones para formar capa(s) de planarización o dieléctrica(s) sobre obleas de silicio, o pueden usarse para encapsular dispositivos electrónicos. La(s) capa(s) o encapsulantes aplicados pueden secarse y curarse entonces para formar una película termoestable, estable de manera termooxidativa.
En otra realización, con el fin de lograr un curado más rápido y/o más completo, la mezcla combinada que puede obtenerse a partir de la resina de poliepóxido, el componente de benzofurano-diol y/o el componente de diepóxido de benzofurano y el agente de aumento de la tenacidad según la presente divulgación en combinación con los agentes de curado mencionados, también puede calentarse a de 50ºC a 300ºC durante un periodo de tiempo de una duración apropiada. Pueden usarse ciclos de calentamiento, tales como, 50ºC durante aproximadamente 0,251 hora, de 150ºC a 200ºC durante aproximadamente 0,5-2 horas, y de 175ºC a 250ºC durante aproximadamente 15 horas.
En algunas realizaciones, puede preferirse hacer reaccionar la totalidad del agente de extensión de cadena con la resina de poliepóxido antes de iniciarse el curado. Esto dependerá, en parte, del porcentaje de agente de extensión de cadena que vaya a incorporarse.
Por tanto, tal como se indicó anteriormente, las composiciones de resina epoxídica de la presente divulgación son adecuadas para su uso en una variedad de aplicaciones, por ejemplo, en el campo de los materiales compuestos tales como en la fabricación de piezas coladas o de productos preimpregnados, en el campo de la electrónica tales como composiciones de encapsulado y moldeo, en procedimientos de laminación, como adhesivos y en protección de superficies tal como un recubrimiento para una tubería o un recipiente.
En otra realización, la presente divulgación proporciona un método de unión de al menos dos sustratos entre sí, que incluye:
a) proporcionar una composición de resina epoxídica que comprende: (i) una resina de poliepóxido; (ii) un componente de benzofurano-diol; un componente de diepóxido de benzofurano o una mezcla de los mismos tal como se describió anteriormente; (iii) un agente de aumento de la tenacidad; y (iv) un agente de curado;
b) aplicar la composición de resina epoxídica a al menos una superficie de uno o más de los sustratos; y
c) acoplar de manera coincidente las superficies de los sustratos que van a unirse entre sí permitiendo que la composición que ha de curarse forme un enlace entre las mismas.
Los sustratos que han de adherirse pueden sujetarse para mayor firmeza durante el curado en aquellas instalaciones en las que podría esperarse el movimiento relativo de los sustratos. Por ejemplo, para adherir dos superficies de sustrato, se aplica una cantidad adherente de la composición de resina epoxídica a al menos una superficie, preferiblemente a ambas superficies, y las superficies se ponen en contacto con la composición entre las mismas. La lisura de las superficies y su holgura determinarán el grosor de película requerido para una unión óptima. La composición de resina epoxídica puede aplicarse a una o más superficies de los sustratos, antes de, de manera posterior a, o simultáneamente con el agente de curado, a un grosor deseado mediante métodos bien conocidos por los expertos en la técnica, tales como, pulverización, inmersión, cepillado, pintado, recubrimiento con
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Claims (1)
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imagen1 imagen2 imagen3 imagen4
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161485902P | 2011-05-13 | 2011-05-13 | |
| US201161485902P | 2011-05-13 | ||
| PCT/US2012/036421 WO2012158363A1 (en) | 2011-05-13 | 2012-05-04 | Epoxy resins with high thermal stability and toughness |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2612236T3 true ES2612236T3 (es) | 2017-05-12 |
Family
ID=47177258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12785700.1T Active ES2612236T3 (es) | 2011-05-13 | 2012-05-04 | Resinas epoxídicas con alta estabilidad y tenacidad |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US9051498B2 (es) |
| EP (1) | EP2751160B1 (es) |
| JP (1) | JP2014513195A (es) |
| KR (1) | KR20140043752A (es) |
| CN (1) | CN103534289B (es) |
| AU (1) | AU2012256282B2 (es) |
| BR (1) | BR112013028011A2 (es) |
| CA (1) | CA2835204A1 (es) |
| ES (1) | ES2612236T3 (es) |
| TW (1) | TW201302832A (es) |
| WO (1) | WO2012158363A1 (es) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102145814B1 (ko) * | 2013-06-26 | 2020-08-19 | 디아이씨 가부시끼가이샤 | 에폭시 화합물, 에폭시 수지, 경화성 조성물, 그 경화물, 반도체 봉지 재료, 및 프린트 배선 기판 |
| CN107636094A (zh) * | 2015-05-20 | 2018-01-26 | 3M创新有限公司 | 高温稳定的单组分可固化热固性组合物 |
| WO2017106596A1 (en) | 2015-12-18 | 2017-06-22 | 3M Innovative Properties Company | Curable epoxy compositions and methods for accelerating the curing of epoxy compositions |
| CN107502261B (zh) * | 2017-09-14 | 2020-07-14 | 广州欣凯化工科技有限公司 | 一种用于木制品的耐高温抗冻树脂胶 |
| FR3073223B1 (fr) * | 2017-11-07 | 2019-11-15 | Arianegroup Sas | Composes biphenyles pluriepoxydes, preparation et utilisations |
| KR102566321B1 (ko) * | 2021-07-26 | 2023-08-14 | 한국화학연구원 | 산 무수물기반 에폭시 화합물, 이를 포함하는 에폭시 수지 이액형 조성물 및 이로부터 제조된 경화물 |
| CN116410714A (zh) * | 2021-12-30 | 2023-07-11 | 天津中油渤星工程科技有限公司 | 一种树脂胶凝材料及其制备方法 |
| CN116144165B (zh) * | 2022-12-27 | 2024-04-02 | 四川大学 | 可回收、可修复的热固性聚氨酯改性沥青材料及其制法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3969372A (en) * | 1975-06-02 | 1976-07-13 | Eastman Kodak Company | 2,3-Dihydro-3,3-dimethyl-2,5-benzofurandiol from isobutyraldehyde and benzoquinone |
| US4568735A (en) * | 1984-11-05 | 1986-02-04 | Shell Oil Company | Process for preparing polyepoxides (II) |
| US5073595A (en) * | 1987-12-23 | 1991-12-17 | Minnesota Mining And Manufacturing Company | Epoxide resin compositions and method |
| GB8901573D0 (en) * | 1989-01-25 | 2001-12-05 | Royal Ordnance Plc | Polymer bonded energetic materials |
| US5151485A (en) * | 1990-11-21 | 1992-09-29 | The Dow Chemical Company | Advanced epoxy compositions, curable compositions and cured products |
| GB9222698D0 (en) * | 1992-10-29 | 1992-12-09 | Ciba Geigy Ag | Expoxides |
| US6486256B1 (en) * | 1998-10-13 | 2002-11-26 | 3M Innovative Properties Company | Composition of epoxy resin, chain extender and polymeric toughener with separate base catalyst |
| US7022777B2 (en) * | 2001-06-28 | 2006-04-04 | General Electric | Moldable poly(arylene ether) thermosetting compositions, methods, and articles |
| JP2004263021A (ja) * | 2003-02-28 | 2004-09-24 | Sumitomo Chem Co Ltd | ポリエーテル樹脂および絶縁膜形成用塗布液 |
| EP2714763B1 (en) * | 2011-05-12 | 2017-03-01 | Huntsman Advanced Materials Americas LLC | Epoxy resins with high thermal stability and toughness |
-
2012
- 2012-05-04 KR KR1020137032978A patent/KR20140043752A/ko not_active Withdrawn
- 2012-05-04 CA CA2835204A patent/CA2835204A1/en not_active Abandoned
- 2012-05-04 AU AU2012256282A patent/AU2012256282B2/en not_active Ceased
- 2012-05-04 WO PCT/US2012/036421 patent/WO2012158363A1/en not_active Ceased
- 2012-05-04 ES ES12785700.1T patent/ES2612236T3/es active Active
- 2012-05-04 US US14/110,300 patent/US9051498B2/en active Active
- 2012-05-04 JP JP2014510370A patent/JP2014513195A/ja active Pending
- 2012-05-04 BR BR112013028011A patent/BR112013028011A2/pt not_active IP Right Cessation
- 2012-05-04 EP EP12785700.1A patent/EP2751160B1/en active Active
- 2012-05-04 CN CN201280023141.4A patent/CN103534289B/zh active Active
- 2012-05-10 TW TW101116720A patent/TW201302832A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2751160A4 (en) | 2015-04-22 |
| CN103534289A (zh) | 2014-01-22 |
| AU2012256282A1 (en) | 2013-10-31 |
| JP2014513195A (ja) | 2014-05-29 |
| KR20140043752A (ko) | 2014-04-10 |
| EP2751160A1 (en) | 2014-07-09 |
| EP2751160B1 (en) | 2016-09-28 |
| AU2012256282B2 (en) | 2015-12-17 |
| CN103534289B (zh) | 2016-08-17 |
| US9051498B2 (en) | 2015-06-09 |
| CA2835204A1 (en) | 2012-11-22 |
| US20140069583A1 (en) | 2014-03-13 |
| TW201302832A (zh) | 2013-01-16 |
| BR112013028011A2 (pt) | 2019-09-24 |
| WO2012158363A1 (en) | 2012-11-22 |
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