Synthesis of a Novel Silicon-containing Epoxy Compound and Its Mechanical Properties for Amine Curing

Abstract

[2-(3,4-epoxy-cyclohexyl)ethyl]dimethyltert-butylsilane was synthesized, using tert-butyldimethylsilane (TBDMS) and 1,2-epoxy-4-vinylcyclohexane (EVC) as the main raw materials and tris(triphenylphosphine) chlororhodium(I) [RhCl(Ph₃P)₃] as the catalyst. [2-(3,4-epoxy-cyclohexyl)ethyl] dimethyltert-butylsilane is a novel kind of silicon-containing epoxide. The factors affecting the reaction yield, such as catalyst use, reaction time and reaction temperature, were investigated, and the synthesized product was characterized and analyzed by FT-IR and ¹H-NMR. A series of amine-curing resins were prepared with [2-(3,4-epoxy-cyclohexyl)ethyl]dimethyltert-butylsilane, bisphenol A epoxy resin (E-51) and modified amine (593 amine). The mechanical properties of cured splines with the different proportions of amine-curing resins were tested. When the content of 593 amine was 20%, the content of E-51 was 75% and the amount of [2-(3,4-epoxy-cyclohexyl) ethyl] dimethyltert-butylsilane was 5%, the mechanical properties of the cured splines were the best with the tensile strength being 23.3 MPa, the elongation at break being 7.8%, and the Young’s modulus being 421.3 MPa.

Keywords

epoxide resin / silicone / amine curing / diluents / mechanical properties

References

[1] JinFL, LiX, ParkSJ. Synthesis and Application of Epoxy Resins: A Review[J]. J. Ind. Eng. Chem., 2015, 29: 1-11

[2] HeP, WangJX, LuFY, et al.. Synergistic Effect of Polyaniline Grafted Basalt Plates for Enhanced Corrosion Protective Performance of Epoxy Coatings[J]. Prog. Org. Coat., 2017, 110: 1-9

[3] PangHW, LiX, ZouYN, et al.. Analysis on Research Progress of Epoxy Resin Anticorrosion Coatings for Metal Equipment[J]. Mater. Prot., 2023, 56(12): 148-156+187

[4] WenYF, ChenC, YeYS, et al.. Advances on Thermally Conductive Epoxy-Based Composites as Electronic Packaging Underfill Materials-A Review[J]. Adv. Mater., 2022, 34522 201 023

[5] ZhangXY, ZhaoY, LiS, et al.. KGM Derived CNTs Foam/Epoxy Composites with Excellent Microwave Absorbing Performance[J]. J. Wuhan. Univ. Technol. Mater. Sci. Ed., 2022, 37(2): 155-162

[6] LiraviF, ToyserkaniE. Additive Manufacturing of Silicone Structures: A Review and Prospective[J]. Addit. Manuf., 2018, 24: 232-242

[7] LiuYX, KangXT, FanZR, et al.. Preparation and Performance of Graphene Oxide Modified Polyurethane Thermal Conductive Insulating Adhesive[J]. J. Wuhan. Univ. Technol. -Mater. Sci. Ed., 2022, 37(5): 1 025-1 031

[8] KhalinaM, BeheshtyMH, SalimiA. The Effect of Reactive Diluent on Mechanical Properties and Microstructure of Epoxy Resins[J]. Polym. Bull., 2019, 76(8): 3 905-3 927

[9] SamynP, BosmansJ, CosemansP. Role of Bio-Based and Fossil-Based Reactive Diluents in Epoxy Coatings with Amine and Phenalkamine Crosslinker[J]. Polym., 2023, 15193 856

[10] OzgulEO, OzkulMH. Effects of Epoxy, Hardener, and Diluent Types on the Workability of Epoxy Mixtures[J]. Constr. Build. Mater., 2018, 158: 369-377

[11] JagtapAR, MoreA. Developments in Reactive Diluents: A Review[J]. Polym. Bull., 2022, 79(8): 5 667-5 708

[12] KurbatovVG, PugachevaTA, MalkovGV, et al.. Effect of Active Diluents on Properties of Epoxy Compounds and Coatings Based on Them[J]. Russ. J. Appl. Chem., 2020, 93(9): 1 340-1 348

[13] XiaoHL, ZhangJN, HouYX, et al.. Process-Specified Emission Factors and Characteristics of VOCs from the Auto-Repair Painting Industry[J]. J. Hazard. Mater., 2024, 467133 666

[14] LiangCR, FengBY, WangSX, et al.. Differentiated Emissions and Secondary Organic Aerosol Formation Potential of Organic Vapor from Industrial Coatings in China[J]. J. Hazard. Mater., 2024, 466133 668

[15] LiuJ, YeDY. Photo-curable Waterborne Polyurethane Acrylates with Low VOCs and Low Odor by Devolatilization and Deodorizing[J]. Prog. Org. Coat., 2023, 185107 930

[16] SreehariH, SethulekshmiAS, SarithaA. Bio Epoxy Coatings: an Emergent Green Anticorrosive Coating for the Future[J]. Macromol. Mater. Eng., 2022, 30782 200 004

[17] HuoSP, MaHL, LiuGF, et al.. Synthesis and Properties of Organosilicon-Grafted Cardanol Novolac Epoxy Resin as a Novel Biobased Reactive Diluent and Toughening Agent[J]. ACS. Omega., 2018, 3(12): 16 403-16 408

[18] OchiM, TakemiyaK, KiyoharaO, et al.. Effect of the Addition of Aramid-Silicone Block Copolymer on the Phase Structure and Toughness of Cured Epoxy Resins Modified with RTV Silicons[J]. Polymer, 2000, 41(1): 195-201

[19] DengX, ZhangBG, LiangJK, et al.. The Crosslinking Mechanism of Camellia Oleifera Protein Adhesive with Amine Resins by ¹³C-NMR and ESI-MS[J]. J. Wuhan. Univ. Technol. Mater. Sci. Ed., 2023, 38(2): 460-466

[20] RudawskaA, FrigioneM. Effect of Diluents on Mechanical Characteristics of Epoxy Compounds[J]. Polym., 2022, 14112 277

RIGHTS & PERMISSIONS

Wuhan University of Technology and Springer-Verlag GmbH Germany, Part of Springer Nature