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WO2024159528A1 - Composition adhésive époxyde en deux parties - Google Patents

Composition adhésive époxyde en deux parties Download PDF

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Publication number
WO2024159528A1
WO2024159528A1 PCT/CN2023/074426 CN2023074426W WO2024159528A1 WO 2024159528 A1 WO2024159528 A1 WO 2024159528A1 CN 2023074426 W CN2023074426 W CN 2023074426W WO 2024159528 A1 WO2024159528 A1 WO 2024159528A1
Authority
WO
WIPO (PCT)
Prior art keywords
weight
adhesive composition
epoxy adhesive
shear strength
groups
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.)
Ceased
Application number
PCT/CN2023/074426
Other languages
English (en)
Inventor
Jinfei Wang
Haiying Li
Yongchun Chen
Qingwei Meng
Linfei WANG
Shaoguang Feng
Yi Zhang
Ping Zhang
Yonghua GONG
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dow Global Technologies LLC
Original Assignee
Dow Global Technologies LLC
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 Dow Global Technologies LLC filed Critical Dow Global Technologies LLC
Priority to PCT/CN2023/074426 priority Critical patent/WO2024159528A1/fr
Publication of WO2024159528A1 publication Critical patent/WO2024159528A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C08G59/18—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
    • C08G59/50—Amines
    • C08G59/504—Amines containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen
    • 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
    • C08G59/50—Amines
    • C08G59/54—Amino amides>
    • 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
    • C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
    • C08G2650/50—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing nitrogen, e.g. polyetheramines or Jeffamines(r)

Definitions

  • the present disclosure relates to a two-part epoxy adhesive composition, particularly a polyamidoamine-based or polyetheramine-based low temperature curing two-part epoxy adhesive composition having improved adhesion with aluminum alloy.
  • EV-car manufacturers are eager to replace steel with aluminum (e.g., VI-type Al) , replace small parts with integrated large castings, and applying adhesives at low temperature in the assembly shop instead of high temperature curing in the body shop.
  • aluminum e.g., VI-type Al
  • 2K (i.e., two-kit or two-part) epoxy or 2K polyurethane adhesive are commonly used for room temperature curing, but the strength is far below the requirements.
  • the inventors After persistent exploration, the inventors have surprisingly developed a two-part epoxy adhesive composition, which exhibits excellent initial lap shear strength, after curing at 120°C for 300 seconds, of greater than 1.0 MPa and a final lap shear strength of greater than18 MPa.
  • a two-part epoxy adhesive composition comprising:
  • Part A which comprises an epoxy resin in the amount of 20-90 %by weight, based on the total weight of part A;
  • Part B which comprises an epoxy hardener based on polyetheramine or polyamidoaminein the amount of 30-70 %by weight, based on the total weight of Part B;
  • Part A and Part B further comprises a silane coupling agent in the amount of 0.5-5 %by weight, based on the total weight of Part A or Part B, respectively;
  • polyetheramine has active hydrogen equivalent weight (AHEW) in a range of 50 to 200; or
  • the polyamidoamine has active hydrogen equivalent weight (AHEW) in a range of 110 to 600, and
  • silane coupling agent comprises epoxy groups and OH-terminated polydimethylsilicone groups.
  • the two-part epoxy adhesive composition as an adhesive agent in fast curing at room temperature.
  • the two-part epoxy adhesive composition as an adhesive agent on aluminum alloy substrate.
  • the two-part epoxy adhesive composition may exhibits a low temperature curing characteristic, excellent initial lap shear strength, after curing at 120°C for 300 seconds, of greater than 1.0 MPa and a final lap shear strength of greater than18 MPa, as well as cohesive failure.
  • part A in the two-part epoxy adhesive composition may comprise an epoxy resin in the amount of 20-90 %by weight, 40-90 %by weight, 60-90 %by weight, 80-90 %by weight, 20-80 %by weight, 40-80 %by weight, 60-80 %by weight, 20-60 %by weight, 40-60 %by weight, 20-40 %by weight, based on the total weight of part A.
  • the epoxy resin may be a liquid epoxy resin, a solid epoxy resin, or a mixture of them.
  • part A also comprises dilute agent in balance.
  • the two-part epoxy adhesive composition is a polyetheramine-based or polyamidoamine-based low temperature curing two-part epoxy adhesive system having improved adhesion with e.g., aluminum alloy.
  • Part B in the two-part epoxy adhesive composition may comprise a polyetheramine or polyamidoamine in the amount of 30-70 %by weight, 30-60 %by weight, 30-50 %by weight, 30-40 %by weight, 40-70 %by weight, 40-60 %by weight, 40-50 %by weight, 50-70 %by weight, 50-60 %by weight, 60-70 %by weight, based on the total weight of part (B) .
  • part B in the two-part epoxy adhesive composition may comprise a silane coupling agent in the amount of 0.5-5 %by weight, 0.5-4 %by weight, 0.5-3 %by weight, 0.5-2 %by weight, 0.5-1 %by weight, 1-5 %by weight, 1-4 %by weight, 1-3 %by weight, 1-2 %by weight, 2-5 %by weight, 2-4 %by weight, 2-3 %by weight, 3-5 %by weight, 3-4 %by weight, 4-5 %by weight, based on the total weight of part (B) .
  • the silane coupling agent can also be added into Part A.
  • active hydrogen equivalent weight also refers to Amine-Hydrogen Equivalent Weight (AHEW) , which is defined as the average molecular weight of the amine compound divided by the Amine Hydrogen Functionality (AHF) .
  • the polyetheramine is an amine hardener having active hydrogen equivalent weight (AHEW) in a range of 50 to 200, 50 to 150, 50 to 100, 50 to 70, 70 to 200, 70 to 150, 70 to 100, 100 to 200, 100 to 150 or 150 to 200.
  • the polyamidoamine is an amine hardener having active hydrogen equivalent weight (AHEW) in a range of 110 to 600, 110 to 500, 110 to 400, 110 to 300, 110 to 200, 200 to 600, 200 to 500, 200 to 400, 200 to 300, 300 to 600, 300 to 500, 300 to 400, 400 to 600, 400 to 500 or 500 to 600.
  • AHEW active hydrogen equivalent weight
  • the polyetheramine is characterized by repeating oxypropylene units in the backbone, which may be represented by the following formula:
  • x is an integer of ⁇ 6, ⁇ 5, ⁇ 4, ⁇ 3, ⁇ 2, or is 1.
  • the polyamidoamine is a reaction product of fatty acid with aliphatic amine in which the fatty acid has a carbon length of 12-18 and aliphatic amine is a polyethylamine.
  • the polyamidoamine may be represented by the following formula:
  • amidoamine can be further dehydrated to form imidazoline. All of amines referred here can also be further reacted with epoxy resin to make an adduct in Part B, so the compatibility with Part A can be improved.
  • the silane coupling agent may comprise epoxy groups and HO-terminated polydimethylsilicone (PDMS) groups.
  • the silane coupling agent may further comprise vinyl groups.
  • the silane coupling agent is a mixture, which contains epoxy (reactive) groups and OH-terminated polydimethylsilicon groups.
  • the epoxy reactive groups may play a role of providing desired compatibility with epoxy groups in Part A and being reactive with curing agents for fast curing.
  • the OH-terminated polydimethylsilicon groups act as a wetting agent, which may wetting a metal (such as Al alloy) substrate quickly for good adhesion due to, e.g., Si-O-Al anchor groups formed by the OH-groups.
  • part A of the two-part epoxy adhesive composition may further comprise optional additives, such as a toughener (such as a core-shell rubber, pre-polymer and etc. ) , a filler and etc.
  • the tougher may include, but not limited to, those formed from elastomers, branched polymers, hyperbranched polymers, dendrimers, rubbery polymers, rubbery copolymers, block copolymers, core-shell particles, oxides or inorganic materials such as clay, polyhedral oligomeric silsesqui oxanes (POSS) , carbonaceous materials (e.g., carbon black, carbon nanotubes, carbon nanofibers, fullerenes) , ceramics and silicon carbides, with or without surface modification or functionalization.
  • PES polyhedral oligomeric silsesqui oxanes
  • Core-shell rubbers are particulate materials (particles) having a rubbery core (e.g., polybutadiene) .
  • a rubbery core e.g., polybutadiene
  • Such materials are known and described in, for example, US Patent Application Publication No. 20150184039, as well as US Patent Application Publication No. 20150240113, and US Patent Nos. 6, 861, 475, 7, 625, 977, 7, 642, 316, 8, 088, 245, and elsewhere.
  • the core-shell rubber particles are nanoparticles (i.e., having an average particle size of less than 1000 nanometers (nm) ) .
  • the average particle size of the core-shell rubber nanoparticles is less than 500 nm, e.g., less than 300 nm, less than 200 nm, less than 100 nm, or even less than 50 nm.
  • such particles are spherical, so the particle size is the diameter; however, if the particles are not spherical, the particle size is defined as the longest dimension of the particle.
  • Suitable core-shell rubbers include, but are not limited to, those sold by Kaneka Corporation under the designation Kaneka Kane Ace, including the Kaneka Kane Ace 15 and 120 series of products, including Kaneka Kane Ace MX 120, Kaneka Kane Ace MX 136, Kaneka Kane Ace MX 137, Kaneka Kane Ace MX 153, Kaneka Kane Ace MX 154, Kaneka Kane Ace MX 156, Kaneka Kane Ace MX170, Kaneka Kane Ace MX 257 and Kaneka Kane Ace MX 120 core-shell rubber dispersions, and mixtures thereof, and those sold by Dow under the designation Parloid.
  • Kaneka Kane Ace including the Kaneka Kane Ace 15 and 120 series of products, including Kaneka Kane Ace MX 120, Kaneka Kane Ace MX 136, Kaneka Kane Ace MX 137, Kaneka Kane Ace MX 153, Kaneka Kane Ace MX 154, Kaneka Kane Ace MX
  • Exemplary inorganic fillers include, but are not limited to metal oxide, fumed silica, calcium carbonate, calcium oxide, kaolin clay, metakaolin clay, talc, mica, mullite, phlogopite, muscovite montmorillonite, smectite, bentonite, illite, chlorite, sepiolite, attapulgite, halloysite, vermiculite, laponite, rectorite, perlite, glass fibers, ceramic fibers, fly ash, Portland cement, concrete mixes or similar inorganic materials, and combinations thereof.
  • the inorganic filler can be a mixture of a plurality of the fillers provided above.
  • the inorganic filler can be a mixture of inorganic fillers comprising at least above two fillers.
  • the inorganic filler is a mixture of fumed silica, calcium carbonate and calcium oxide.
  • the toughener may be in the amount of 0-70 %by weight, 0-50 %by weight, 0-30 %by weight, 0-10 %by weight, 10-70 %by weight, 10-50 %by weight, 10-30 %by weight, 30-70 %by weight, 30-50 %by weight, 50-70 %by weight; and the filler may be in the amount of 8-30 %by weight, 8-20 %by weight, 8-10 %by weight, 10-30 %by weight, 10-20 %by weight, 20-30 %by weight, based on the total weight of part A.
  • volume ratio of part A and part B in the two-part epoxy adhesive composition may be in a range from 8: 1 to 1: 1, from 8: 1 to 2: 1, from 8: 1 to 4: 1, from 8: 1 to 6: 1, from 6: 1 to 1: 1, from 6: 1 to 2: 1, from 6: 1 to 4: 1, from 4: 1 to 1: 1, from 4: 1 to 2: 1, or from 2: 1 to 1: 1.
  • the silane coupling agent may be a single compound comprising epoxy groups and OH-terminated polydimethylsilicone groups; or a mixture which comprises epoxy groups and OH-terminated polydimethylsilicone groups.
  • the two-part epoxy adhesive composition may be used as an adhesive agent in fast curing at low temperature, such as room temperature, a temperature of ⁇ 120°C.
  • the two-part epoxy adhesive composition may be used as an adhesive agent on metal substrates such as aluminum alloy substrate.
  • the two-part epoxy adhesive composition may exhibit a low temperature curing characteristic, excellent initial lap shear strength, after curing at 120°C for 300 seconds, of greater than 1.0MPa and a final lap shear strength of greater than18MPa, as well as cohesive failure.
  • NPEL 128, a solid epoxy resin D. E. R. 671, a core-shell rubber Kane Ace MX 154, a pre-polymer ADEKATM QR-9466, 3604, fumed Silica H18, calcium carbonate Omya 520, calcium oxide JYQ-01 and silane coupling agent listed in Tables 2 and 3 were mixed in a container containing a dilute agent DY-C equipped with a high-speed mixing machine, to form uniform Part A. Then, the uniform Part A and a polyetheramine, e.g., D-400, were mixed with a speed of 2000 rpm for 2 minutes, to form the two-part epoxy adhesive composition.
  • a polyetheramine e.g., D-400
  • Table 3 shows performance of the compositions according to Inventive Examples 1-3, 9 and Comparative Examples 1-14, 26.
  • Failure mode AF-Adhesive failure; and CF-Cohesive failure.
  • synergy of silane coupling agent with curing agent in the two-part epoxy adhesive composition shows improved bonding performance both at initial lap shear strength and final lap shear strength.
  • CE1 a single polyetheramine was used as curing hardener, both initial lap shear strength and final lap shear strength were weak.
  • Even using a single silane agent AE-40-2, AE-40-3, AE-40-4, AE-40-5, AE-40-6) , the lap shear strength was improved but it was not significant.
  • Adding 1 ⁇ 5%silane coupling agent into Part B can improve both initial lap shear strength and final lap shear strength (AE-40-1, AE-76, AE-77, AE-78) .
  • combinations comprising other amine hardeners AE-70 ⁇ 75, AE-79, AE-46-1, AE-46-2
  • silane coupling agents the lap shear strength was weak.
  • NPEL 128, a solid epoxy resin D. E. R. 671, a core-shell rubber Kane Ace MX 154, a pre-polymer ADEKA TM QR-9466, 3604, fumed Silica H18, calcium carbonate Omya 520, calcium oxide JYQ-01 and silane coupling agent listed in Tables 4 and 5 were mixed in a container containing a dilute agent DY-C equipped with a high-speed mixing machine, to form uniform Part A. Then, the uniform Part A and a polyamidoamine, e.g., 450 Hardener, were mixed with a speed of 2000 rpm for 2 minutes, to form the two-part epoxy adhesive composition.
  • a polyamidoamine e.g., 450 Hardener
  • Table 5 shows performance of the compositions according to Inventive Examples 4-8 and Comparative Examples 15-25, 27-28.
  • Failure mode AF-Adhesive failure; and CF-Cohesive failure.
  • synergy of silane coupling agent with curing agent in the two-part epoxy adhesive composition shows improved bonding performance both at initial lap shear strength and final lap shear strength.
  • CE15 a single polyamidoamine was used as curing hardener, both initial lap shear strength and final lap shear strength were weak.
  • CE3, CE4, CE5, CE6 the lap shear strength was improved but it was not significant.
  • Adding 1 ⁇ 5%silane coupling agent into Part B can improve both initial lap shear strength and final lap shear strength (AE-40-1, AE-76, AE-77) .
  • the lap shear strength was weak (CE8-CE12, AE-46-3, AE-45-4) .
  • Adhesion failue represents the interfacial failure between adhesive and substrate
  • Cohesive failure represents the adhesion self fracture, on the substrate there is adhesive residue.
  • the adhesive coated on the VI-Al substrate one side, the subastrate is 100mm*25mm*2mm, the coating area is 12.5mm*5mm, the coating thickness limited by 0.2mm diameter metal wire. Then the other VI-Al substrate lap jointed with it, get rid of the excess the adhesive sample, at last clamped the both side by dovetail holding 1hour at 23 ⁇ 2°C, the moisture is (50 ⁇ 10) % environment.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Epoxy Resins (AREA)

Abstract

La composition adhésive époxyde en deux parties peut comprendre une partie A et une partie B ; la partie A comprend une résine époxyde en une quantité de 20 à 90 % en poids, sur la base du poids total de la partie A ; et la partie B comprend une polyétheramine ou une polyamidoamine en une quantité de 30 à 70 % en poids, sur la base du poids total de la partie B ; au moins l'une de la partie A et de la partie B comprenant en outre un agent de couplage de type silane en la quantité de 0,5 à 5 % en poids, sur la base du poids total de la partie A ou de la partie B, respectivement ; la polyétheramine a un poids équivalent d'hydrogène actif (AHEW) dans une plage de 50 à 200 ; la polyamidoamine a un poids équivalent d'hydrogène actif (AHEW) dans une plage de 110 à 600, et l'agent de couplage de type silane comprend des groupes époxyde et des groupes de polydiméthylsiloxane à terminaison OH. Les compositions adhésives époxyde en deux parties présentent une caractéristique de durcissement à basse température, une excellente résistance au cisaillement de recouvrement initial, après durcissement à 120 °C pendant 300 secondes, supérieure à 1,0 MPa, une résistance au cisaillement de recouvrement finale supérieure à 18 MPa, et une défaillance cohésive, ainsi qu'une excellente adhérence à divers substrats, en particulier un substrat en alliage d'Al.
PCT/CN2023/074426 2023-02-03 2023-02-03 Composition adhésive époxyde en deux parties Ceased WO2024159528A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/CN2023/074426 WO2024159528A1 (fr) 2023-02-03 2023-02-03 Composition adhésive époxyde en deux parties

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2023/074426 WO2024159528A1 (fr) 2023-02-03 2023-02-03 Composition adhésive époxyde en deux parties

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Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6861475B2 (en) 2002-10-16 2005-03-01 Rohm And Haas Company Smooth, flexible powder coatings
US7625977B2 (en) 2007-06-20 2009-12-01 Dow Global Technologies Inc. Adhesive of epoxy resin, toughener and blocked isocyanate polytetrahydrofuran toughener
US7642316B2 (en) 2004-10-14 2010-01-05 Dow Global Technologies, Inc. Rubber modified monovinylidene aromatic polymers and fabricated articles prepared therefrom
US8088245B2 (en) 2007-04-11 2012-01-03 Dow Global Technologies Llc Structural epoxy resins containing core-shell rubbers
EP2402394A1 (fr) * 2009-02-27 2012-01-04 Henkel (China) Investment Company Ltd. Composition adhésive structurale d'époxy durcissable à température ambiante et procédé de préparation de celle-ci
CN104312513A (zh) * 2014-11-17 2015-01-28 南京艾布纳密封技术有限公司 一种双组分环氧电子灌封硅胶
US20150175856A1 (en) * 2012-07-20 2015-06-25 Namics Corporation Liquid sealing material and electronic component using same
US20150184039A1 (en) 2012-08-27 2015-07-02 Dow Global Technologies Llc Accelerated and toughened two part epoxy adhesives
US20150240113A1 (en) 2012-09-17 2015-08-27 3N Innovative Properties Company Powder coating epoxy compositions, methods, and articles
US20190359816A1 (en) * 2017-01-26 2019-11-28 Huntsman Advanced Materials Licensing (Switzerland) Gmbh Thermosetting Epoxy Resin Composition for the Preparation of Articles for Electrical Engineering, and the Articles Obtained Therefrom
WO2021220090A1 (fr) * 2020-04-28 2021-11-04 3M Innovative Properties Company Composition durcissable

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6861475B2 (en) 2002-10-16 2005-03-01 Rohm And Haas Company Smooth, flexible powder coatings
US7642316B2 (en) 2004-10-14 2010-01-05 Dow Global Technologies, Inc. Rubber modified monovinylidene aromatic polymers and fabricated articles prepared therefrom
US8088245B2 (en) 2007-04-11 2012-01-03 Dow Global Technologies Llc Structural epoxy resins containing core-shell rubbers
US7625977B2 (en) 2007-06-20 2009-12-01 Dow Global Technologies Inc. Adhesive of epoxy resin, toughener and blocked isocyanate polytetrahydrofuran toughener
EP2402394A1 (fr) * 2009-02-27 2012-01-04 Henkel (China) Investment Company Ltd. Composition adhésive structurale d'époxy durcissable à température ambiante et procédé de préparation de celle-ci
US20150175856A1 (en) * 2012-07-20 2015-06-25 Namics Corporation Liquid sealing material and electronic component using same
US20150184039A1 (en) 2012-08-27 2015-07-02 Dow Global Technologies Llc Accelerated and toughened two part epoxy adhesives
US20150240113A1 (en) 2012-09-17 2015-08-27 3N Innovative Properties Company Powder coating epoxy compositions, methods, and articles
CN104312513A (zh) * 2014-11-17 2015-01-28 南京艾布纳密封技术有限公司 一种双组分环氧电子灌封硅胶
US20190359816A1 (en) * 2017-01-26 2019-11-28 Huntsman Advanced Materials Licensing (Switzerland) Gmbh Thermosetting Epoxy Resin Composition for the Preparation of Articles for Electrical Engineering, and the Articles Obtained Therefrom
WO2021220090A1 (fr) * 2020-04-28 2021-11-04 3M Innovative Properties Company Composition durcissable

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