WO2024023846A1 - Matériau à changement de phase à base d'époxy, composition et procédé correspondants - Google Patents

Matériau à changement de phase à base d'époxy, composition et procédé correspondants Download PDF

Info

Publication number
WO2024023846A1
WO2024023846A1 PCT/IN2023/050721 IN2023050721W WO2024023846A1 WO 2024023846 A1 WO2024023846 A1 WO 2024023846A1 IN 2023050721 W IN2023050721 W IN 2023050721W WO 2024023846 A1 WO2024023846 A1 WO 2024023846A1
Authority
WO
WIPO (PCT)
Prior art keywords
epoxy
phase change
based phase
change material
organic compound
Prior art date
Application number
PCT/IN2023/050721
Other languages
English (en)
Inventor
Amol Murlidharrao KENDHALE
Shashikant Sangmeshwar Paymalle
Original Assignee
Elantas Beck India Limited
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Elantas Beck India Limited filed Critical Elantas Beck India Limited
Publication of WO2024023846A1 publication Critical patent/WO2024023846A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/02—Materials undergoing a change of physical state when used
    • C09K5/06—Materials undergoing a change of physical state when used the change of state being from liquid to solid or vice versa
    • C09K5/063—Materials absorbing or liberating heat during crystallisation; Heat storage materials

Definitions

  • the present disclosure relates to an epoxy-based material. Specifically, the present disclosure relates to an epoxy-based phase change material. More specifically, the present disclosure relates to an epoxy resin modified with an organic compound having two or more terminal hydroxyl groups. Further, the present disclosure relates to a process for making the epoxy-based phase change material. The present disclosure also relates to an epoxy-based phase change composition comprising an epoxy-based phase change material, a solvent and a filler.
  • a phase change material is a substance which releases or absorbs sufficient energy at phase transition to provide useful heat/cooling.
  • thermal energy is absorbed and released (known as latent heat).
  • Many materials have the ability to absorb a large quantity of heat energy during the phase transition. At different temperatures, different materials melt and solidify, and they may absorb varying amounts of heat energy.
  • PCMs can be used to control the temperature in a wide range of applications since they melt and solidify at precise, specified temperatures. Amongst various applications, PCM is also utilized widely in automobile applications. PCMs are being researched in relation to potting applications.
  • Thermal energy can be stored in a material as sensible heat, latent heat and thermochemical energy etc., and may be a combination of more than one. Latent heat storage is considered the most convenient and efficient method for this purpose.
  • PCMs have the further advantages of high heat-storage ability, thermal stability and easily controlled phase-change processes. A large number of organic, inorganic, polymeric, and eutectic PCMs have been designed owing to increasing interest in these materials, combined with understanding of their potential.
  • Patent literature US 7,488,773 B2 discloses silicone rubber materials containing finely divided phase change materials such as crystalline alkyl hydrocarbons or salt hydrates.
  • the phase change material provides a thermo-regulating system which enhances the thermal performance of silicone rubber materials substantially.
  • Patent literature US005755987A describes a phase change material comprising a dibasic ester.
  • Patent literature WO2021035649A1 discloses a resin type phase change energy storage material comprising resin, phase change powder and curing agent.
  • Patent literature CN107541027B discloses a phase-change energy storage material prepared from polymer matrix material, phase change material, porous filler and heat conducting filler.
  • the phase change material used is paraffin wax. It is to be noted that paraffin wax as a phase change material has low temperature stability or lower operation temperature.
  • Patent literature CA2720844A1 discloses a curable epoxy-based composition comprising an epoxy resin, a hardener, and an endothermic transition additive (PCM).
  • the endothermic transition additive (PCM) discloses are such as an organic polymer, including thermoplastic materials or inorganic materials including sodium thiosulfate pentahydrate, sodium acetate trihydrate, sodium sulfate decahydrate, barium hydroxide hydrate, nickel nitrate tetrahydrate, zinc nitrate hexahydrate, blends thereof, alloys thereof, and eutectic mixtures thereof.
  • phase change material which allows improvement in performance of electronic components, safety and has ability to reduce and even eliminate the potential for thermal runaway or propagation in electronic devices. It is still desired to obtain a phase change material which is suitable for a broad range of applications.
  • the present disclosure addresses above by providing an epoxy -based phase change material, composition and a method of preparing the same.
  • the present disclosure provides an epoxy-based phase change material and a method of preparing the same.
  • the present disclosure also relates to an epoxy-based phase change composition comprising an epoxy-based phase change material.
  • the present disclosure also provides products based on epoxy-based phase change material which demonstrates phase change temperature of -40-55 °C.
  • the present disclosure relates to a solid to semisolid (and reverse) epoxy-based phase change material comprising a reaction product of an epoxy resin, an organic compound having two or more terminal hydroxyl groups, and a coupling agent, wherein the epoxy-based phase change material is represented by the following formula (1): wherein ‘A’ represents the backbone of the epoxy resin, ‘B’ represents backbone of an organic compound, and ‘n’ represents an integer having value 1 to 12.
  • An epoxy equivalent weight (EEW) of the epoxy-based phase change material is the range of 300 - 400.
  • the epoxy-based phase change material improves performance of electronic components, safety and has ability to reduce and even eliminate the potential for thermal runaway or propagation in electronic devices. Further, the present disclosure relates to a process for making the epoxy-based phase change material.
  • the present disclosure also relates to an epoxy-based phase change composition
  • an epoxy-based phase change composition comprising an epoxy-based phase change material.
  • the epoxy-based phase change composition is prepared by mixing an epoxy-based phase change material, a solvent and a filler.
  • compositions comprising a list of components does not include only those components but may include other components not expressly listed or inherent to such process.
  • one or more elements in a composition, system or process proceeded by “comprises... a” does not, without more constraints, preclude the existence of other elements or additional elements in the system or process. Accordingly, one aspect of the present disclosure relates to an epoxy-based phase change material comprising a reaction product of:
  • a coupling agent wherein the epoxy -based phase change material is represented by the following formula (1): wherein ‘A’ represents the backbone of the epoxy resin, wherein ‘B’ represents backbone of an organic compound having two or more terminal hydroxyl groups, and wherein ‘n’ represents an integer having value 1 to 12, and wherein the organic compound is an aromatic organic compound having two or more terminal hydroxyl groups or a combination of an aromatic and non-aromatic organic compound having two or more terminal hydroxyl groups.
  • the ratio of epoxy resin to organic compound is in the range of 7:1 - 10:1.5, preferably in the range of 7.5: 1.1 - 8.5 :1.2.
  • the epoxy equivalent weight (EEW) of the epoxy based phase change material is the range of 300 - 400.
  • the EEW is measured by a titration method involving following steps:
  • step 1 Adding in step 1, 10 ml of 1,4 dioxane and 10 ml chlorobenzene in conical flask and stir until the sample is dissolved completely.
  • step 2 Adding in step 2, 10 ml of TEAB solution and stir.
  • step 3 Adding in step 3, 2-3 drops of crystal violet indicator and stir well.
  • the phase change temperature is between 40 to 55 °C.
  • the phase change temperature is measured by following methods.
  • the PCM material is placed in a petri dish and is gradually heated inside an oven at a temperature in the range of 25° C to 60° C and recording the temperature wherein the phase transition occurs.
  • the PCM temperature can also be measured by putting PCM material in the flask equipped with thermometer and then gradually heating it and then recording the temperature wherein the phase transition occurs.
  • the epoxy oligomers or polymers suitable for the compositions of the present disclosure include those derived from Bisphenol-A, hydrogenated Bisphenol-A, Bisphenol-F, Bisphenol-S, novolac epoxies, phenol novolac epoxies, cresol novolac epoxies, N-glycidyl epoxies, glyoxal epoxies dicyclopentadiene phenolic epoxies, silicone-modified epoxies, and epsilon- caprolactone modified epoxies. Combinations of different halogenated epoxy oligomers can also be used.
  • the backbone of the epoxy resin ‘A’ is selected from bisphenol-A based epoxy resins such as Bisphenol A diglycidyl ether (DGEBA or BADGE), or bisphenol-F based epoxy resin (BPF).
  • bisphenol-A based epoxy resins such as Bisphenol A diglycidyl ether (DGEBA or BADGE), or bisphenol-F based epoxy resin (BPF).
  • the bisphenol-A based epoxy resins and bisphenol-F based epoxy resin are commercially available such as EPIKOTE 828/EPOTEC YD 128 and EPIKOTE 862.
  • backbone of the epoxy resin ‘A’ is preferably selected from but not limited to halogenated bisphenols-A based resins or bisphenol-F based resins, or mixtures thereof.
  • the aromatic organic compound having two or more terminal hydroxyl groups is selected from hydroquinone, resorcinol, catechol, or mixtures thereof.
  • the non-aromatic organic compound having two or more terminal hydroxyl groups is selected from 1,6-hexanediol, 1,4-butanediol or mixtures thereof.
  • the coupling agent can be used as known in the art and is not limited, but preferably selected from triphenyl phosphonium acetate, or triphenylphosphine or mixtures thereof.
  • the amount of epoxy resin is selected from 50 - 99 wt%, preferably selected in the range of 70-90 wt%.
  • the amount of organic compound having two or more terminal hydroxyl groups is selected from 1 -50 wt%, preferably selected in the range of 10 -30 wt %.
  • the amount of coupling agent is selected from 0.005- 3 wt%, preferably 0.01-0.1 wt%.
  • Another aspect of the present disclosure relates to a method of preparing an epoxy-based phase change material comprising the following steps: a. adding an epoxy resin, an organic compound having two or more terminal hydroxyl groups and a coupling agent in a vessel followed by stirring, b. increasing the temperature from room temperature to a minimum of 70 °C, preferably between 70 °C to 140 °C and maintaining the temperature for 2 to 5 hours to provide an epoxy-based phase change material.
  • the epoxy -based phase change material is represented by the following formula (1): wherein ‘A’ represents the backbone of the epoxy resin, wherein ‘B’ represents backbone of an organic compound having two or more terminal hydroxyl groups, and wherein ‘n’ represents an integer having value 1 to 12, and wherein the organic compound is an aromatic organic compound having two or more terminal hydroxyl groups or a combination of an aromatic and non-aromatic organic compound having two or more terminal hydroxyl groups.
  • Yet another aspect of the present disclosure relates to an epoxy -based phase change composition
  • an epoxy -based phase change composition comprising an epoxy-based phase change material, a solvent and a filler.
  • the epoxy-based phase change composition is prepared by mixing an epoxy-based phase change material, a solvent and a filler.
  • the amount of the epoxy-based phase change material is in the range of 20 - 70 wt%.
  • the filler is selected from but not limited to aluminum trihydrate (ATH), alumina, boron nitride, aluminum nitride, zinc oxide, or combinations thereof.
  • ATH aluminum trihydrate
  • alumina aluminum trihydrate
  • boron nitride aluminum nitride
  • zinc oxide zinc oxide
  • the amount of filler is selected from 10 - 90 wt%, preferably selected in the range of 30 - 70 wt%.
  • the solvent is selected from but not limited to propylene carbonate, 1,6- hexanediol glycidyl ether, phenyl glycidyl ether or mixtures thereof.
  • the amount of solvent is selected from 5 - 20 wt%.
  • the latent heat capacity of the thermally conductive phase change material at 40°C is in the range of 17580 to 18500 KJ/kg by DSC analysis.
  • the epoxy-based phase change material is used in insulated gate bipolar transistor (IGBT) gel applications, in energy storage devices and in electric vehicle potting applications.
  • IGBT insulated gate bipolar transistor
  • Another aspect of the present disclosure relates to products based on epoxy-based phase change material which demonstrates phase change temperature of -40-55 °C along with improved thermal conductivity (TC) of -15-25 %. Further salient features of the epoxy-based phase change material and the method of preparing the same providing the disclosed enhancements are discussed in the examples provided below.
  • PCM 1 Standard epoxy resin DGEBA (89.58 parts by wt%), resorcinol (10.39 parts by wt%) and ethyl triphenyl phosphonium acetate (0.03 parts by wt%) were charged in a clean, dry kettle and stirred. The reaction temperature was increased from room temp to 70°C for 30 min, then 80°C for 30 min., 100°C for another 30 min, 120°C for 1 hr and then 130-140°C for 90 min. The reaction mixture was cooled and the product having a dark brown solid was obtained.
  • the PCM had epoxy equivalent weight (EEW) of 330 -350.
  • PCM 2 Standard epoxy resin DGEBA (89.58 parts by wt%), Catechol (10.39 parts by wt%) and ethyl triphenyl phosphonium acetate (0.03 parts by wt%) were charged in a clean, dry kettle and stirred. The reaction temperature was increased from room temp to 70°C for 30 min, then 80°C for 30 min., 100°C for another 30 min, 120°C for Bit and then 130-140°C for 90 min. The reaction mixture was cooled and the product having a dark brown solid was obtained.
  • the PCM had epoxy equivalent weight (EEW) of 320 -350.
  • PCM based on bisphenol F epoxy resin
  • PCM 3 Bisphenol F Epoxy resin (89.58 parts by wt%), hydroquinone (10.39 parts by wt%) and ethyl triphenyl phosphonium acetate (0.03 parts by wt%) were charged in a clean, dry kettle and stirred. The reaction temperature was increased from room temp to 70°C for 30 min, then 80°C for 30 min., 100°C for another 30 min, 120°C for Bit and then 130-140°C for 90 min. The reaction mixture was cooled and the product having a dark brown solid was obtained.
  • the PCM had epoxy equivalent weight (EEW) of 300 -350.
  • PCM 4 Bisphenol F Epoxy resin (89.58 parts by wt%), Resorcinol (10.39 parts by wt%) and ethyl triphenyl phosphonium acetate (0.03 parts by wt%) were charged in a clean, dry kettle and stirred. The reaction temperature increased from room temp to 70°C for 30 min, then 80°C for 30 min., 100°C for another 30 min, 120°C for Bit and then 130-140°C for 90 min. The reaction mixture was cooled and the product having a dark brown solid was obtained. The PCM had epoxy equivalent weight (EEW) of 310 -350.
  • EW epoxy equivalent weight
  • PCM 5 Bisphenol F Epoxy resin (89.58 parts by wt%), Catechol (10.39 parts by wt%) and ethyl triphenyl phosphonium acetate (0.03 parts by wt%) were charged in a clean, dry kettle and stirred. The reaction temperature was increased from room temp to 70°C for 30 min, then 80°C for 30-40 min., 100°C for another 30 min, 120°C for Bit and then 130-140°C for 2hr. The reaction mixture was cooled and the product having a dark brown solid was obtained.
  • the PCM had epoxy equivalent weight (EEW) of 320 -350.
  • PCM 6 Standard epoxy resin DGEBA (87.29 parts by wt%), hydroquinone (11.19 parts by wt%), 1,6-Hexanediol (1.46 parts by wt%), and ethyl triphenyl phosphonium acetate (0.06 parts by wt%) were charged in a clean, dry kettle and stirred. The reaction temperature was increased from room temp to 220°C and maintained for 4hr. The reaction mixture was cooled and the product having a dark brown solid was obtained.
  • the PCM had epoxy equivalent weight (EEW) of 360 -380.
  • PCM 7 Standard epoxy resin DGEBA (87.29 parts by wt%), Resorcinol (11.20 parts by wt%), 1,6-Hexanediol (1.46 parts by wt%), and ethyl triphenyl phosphonium acetate (0.03 parts by wt%) were charged in a clean, dry kettle and stirred. The reaction temperature was increased from room temp to 220°C and maintained for 4hr. The reaction mixture was cooled and the product having a dark brown solid was obtained.
  • the PCM had epoxy equivalent weight (EEW) of 370 -390.
  • PCM 8 Standard epoxy resin DGEBA (YD 128) (87.30 parts by wt%), Catechol (11.19 parts by wt%), 1,6-Hexanediol (1.46 parts by wt%), and ethyl triphenyl phosphonium acetate (0.03 parts by wt%) were charged in a clean, dry kettle and stirred. The reaction temperature was increased from room temp to 220°C and maintained for 4hr and finally 250°C for Jackpot. The reaction mixture was cooled and the product having a dark brown solid was obtained.
  • the PCM had epoxy equivalent weight (EEW) of 355 -380.
  • Control 1 (Comparative example) Control 1: Standard epoxy resin DGEBA (85.14 parts by wt%), 1,6-Hexanediol (14.81 parts by wt%), and ethyl triphenyl phosphonium acetate (0.05 parts by wt%) were charged in a clean, dry kettle and stirred. The reaction temperature was increased from room temp to 220°C and maintained for 4hr. Cool the reaction mixture. The reaction mixture was cooled and the product having a dark brown solid was obtained.
  • the Control 1 had an epoxy equivalent weight (EEW) of 360 -375.
  • the epoxy-based phase change composition is prepared by mixing an epoxy-based phase change material (PCM) with a filler and a solvent in a vessel.
  • PCM epoxy-based phase change material
  • the amount of the epoxy-based phase change material is in the range of 20 - 70 wt% with respect to the amount of filler being in the range of 30 - 80 wt%.
  • the fillers used in examples of present disclosure are Aluminum oxide/ Alumina and Boron nitride.
  • the solvent used in examples of present disclosure is propylene carbonate.
  • PCM phase change material

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Combustion & Propulsion (AREA)
  • Thermal Sciences (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Resins (AREA)

Abstract

La présente invention concerne un matériau à changement de phase à base d'époxy et un procédé de fabrication du matériau à changement de phase à base d'époxy. Le matériau à changement de phase à base d'époxy comprend un produit de réaction d'une résine époxy, d'un composé organique présentant deux groupes hydroxyle terminaux ou plus et d'un agent de couplage. Le poids équivalent en époxy (EEW) du matériau à changement de phase à base d'époxy est situé dans la plage de 300 à 400. Le matériau à changement de phase à base d'époxy améliore la performance de composants électroniques, la sécurité et présente une aptitude à réduire et même à éliminer le potentiel d'emballement ou de propagation thermique dans des dispositifs électroniques. La présente invention concerne également une composition à changement de phase à base d'époxy comprenant un matériau à changement de phase à base d'époxy, un solvant et une charge.
PCT/IN2023/050721 2022-07-29 2023-07-27 Matériau à changement de phase à base d'époxy, composition et procédé correspondants WO2024023846A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN202221043523 2022-07-29
IN202221043523 2022-07-29

Publications (1)

Publication Number Publication Date
WO2024023846A1 true WO2024023846A1 (fr) 2024-02-01

Family

ID=87974222

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2023/050721 WO2024023846A1 (fr) 2022-07-29 2023-07-27 Matériau à changement de phase à base d'époxy, composition et procédé correspondants

Country Status (1)

Country Link
WO (1) WO2024023846A1 (fr)

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5755987A (en) 1996-08-23 1998-05-26 The Dow Chemical Company Dibasic ester based phase change material compositions
JP3632285B2 (ja) * 1996-03-22 2005-03-23 東都化成株式会社 フェノール性水酸基含有変性エポキシ樹脂、その製造方法及びその粉体塗料組成物
US7488773B2 (en) 2002-01-23 2009-02-10 Barbara Hildegard Pause Material made from a silicone rubber, production process, and application
CA2720844A1 (fr) 2008-04-14 2009-10-22 Dow Global Technologies Inc. Utilisation d'une matiere de charge qui subit une transition de phase endothermique pour abaisser la chaleur exothermique de reaction de compositions a base d'epoxyde
CN107541027A (zh) 2017-05-19 2018-01-05 上海叹止新材料科技有限公司 一种聚合物基相变储能材料及其制备方法
US20190225742A1 (en) * 2016-08-25 2019-07-25 Stepan Company Polyester-epoxide polymer compositions
US20200377646A1 (en) * 2018-02-23 2020-12-03 Stepan Company Solid-solid phase-change materials
WO2021035649A1 (fr) 2019-08-29 2021-03-04 张立强 Matériau de stockage d'énergie à changement de phase de type résine et son procédé de préparation
US20220041798A1 (en) * 2019-04-26 2022-02-10 Stepan Company Polyol-epoxide polymers for nvh damping applications

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3632285B2 (ja) * 1996-03-22 2005-03-23 東都化成株式会社 フェノール性水酸基含有変性エポキシ樹脂、その製造方法及びその粉体塗料組成物
US5755987A (en) 1996-08-23 1998-05-26 The Dow Chemical Company Dibasic ester based phase change material compositions
US7488773B2 (en) 2002-01-23 2009-02-10 Barbara Hildegard Pause Material made from a silicone rubber, production process, and application
CA2720844A1 (fr) 2008-04-14 2009-10-22 Dow Global Technologies Inc. Utilisation d'une matiere de charge qui subit une transition de phase endothermique pour abaisser la chaleur exothermique de reaction de compositions a base d'epoxyde
US20190225742A1 (en) * 2016-08-25 2019-07-25 Stepan Company Polyester-epoxide polymer compositions
CN107541027A (zh) 2017-05-19 2018-01-05 上海叹止新材料科技有限公司 一种聚合物基相变储能材料及其制备方法
US20200377646A1 (en) * 2018-02-23 2020-12-03 Stepan Company Solid-solid phase-change materials
US20220041798A1 (en) * 2019-04-26 2022-02-10 Stepan Company Polyol-epoxide polymers for nvh damping applications
WO2021035649A1 (fr) 2019-08-29 2021-03-04 张立强 Matériau de stockage d'énergie à changement de phase de type résine et son procédé de préparation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
ROY CHOUDHURY SHREYA ET AL: "study", vol. 138, no. 39, 15 October 2021 (2021-10-15), US, pages 50995, XP093022934, ISSN: 0021-8995, Retrieved from the Internet <URL:https://onlinelibrary.wiley.com/doi/full-xml/10.1002/app.50995> DOI: 10.1002/app.50995 *

Similar Documents

Publication Publication Date Title
JP7306987B2 (ja) 硬化樹脂用組成物、該組成物の硬化物、該組成物および該硬化物の製造方法、ならびに半導体装置
TWI742211B (zh) 硬化樹脂用組成物、該硬化樹脂用組成物之硬化物及硬化方法以及半導體裝置
EP3702390B1 (fr) Composition pour résines réticulables, produit réticulé de ladite composition, procédé de préparation de ladite composition et dudit produit réticulé, et dispositif semi-conducteur
JP2006525377A (ja) 難燃性成形用組成物
JP7086983B2 (ja) 硬化樹脂用組成物、該組成物の硬化物、該組成物および該硬化物の製造方法、ならびに半導体装置
EP3702388B1 (fr) Composition pour résine à durcissement, objet durci de cette composition, procédés de fabrication de cette composition et de cet objet durci, et dispositif à semi-conducteurs
JPS6230215B2 (fr)
JP5079721B2 (ja) エポキシ樹脂組成物および成形物
JP5209556B2 (ja) エポキシ樹脂組成物および成形物
WO2024023846A1 (fr) Matériau à changement de phase à base d&#39;époxy, composition et procédé correspondants
TW202100707A (zh) 硬化樹脂用組合物、該組合物之硬化物、該組合物及該硬化物之製造方法、以及半導體裝置
JP3369323B2 (ja) 半導体封止用エポキシ樹脂組成物
JP2023000691A (ja) エポキシ樹脂組成物および硬化物
JP2002047337A (ja) 封止用樹脂組成物および半導体封止装置
JP7410052B2 (ja) 硬化樹脂用組成物、該組成物の硬化物、該組成物および該硬化物の製造方法、ならびに半導体装置
JPS61183317A (ja) 低温速硬化型エポキシ樹脂組成物
TW201127898A (en) High thermal conductivity, halogen-free flame-retardant resin composition and its pre-impregnated body and coating materials for printed circuit boards
JPH11292956A (ja) エポキシ樹脂組成物
JP2021091799A (ja) エポキシ樹脂組成物および成形物
JP4000658B2 (ja) 固形エポキシ樹脂組成物
JP3791711B2 (ja) エポキシ樹脂組成物
JP3145687B2 (ja) エポキシ樹脂組成物および半導体封止装置
JP2021195459A (ja) エポキシ樹脂組成物及び成形物
JPS637569B2 (fr)
KR20240088722A (ko) 봉지재용 말레이미드 수지 혼합물, 말레이미드 수지 조성물 및 그의 경화물

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 23768009

Country of ref document: EP

Kind code of ref document: A1