Synthesis and characterization of a thermosetting resins based on 4-(N-maleimidophenylester) hydroxypropylmethacrylate

Abstract

A hybrid monomer on 4-(N-maleimidophenylester) hydroxypropylmethacrylate (MPEHPM) possessing both maleimide and methacrylate groups has been synthesized from 4-N-carboxyphenylmaleimide (CPMI) and glycidylmethacrylate (GMA) in the presence of triethylbenzylamonium chloride (TEBAC) as a catalyst. The monomer was modified with diaminodiphenylmethane bismaleimide (MDABMI) and diglycidyl bisphenol A (DGEBA) and cured in the presence of 4,4'-methylenedianiline (MDA). The presence of an epoxy ring, amino groups and the both types of double bonds, makes these systems potential materials for obtaining thermosetting products. The curing and thermal stability of the crosslinked products were studied by differential scanning calorimetry (DSC) and TGA techniques.SYNTEZA I CHARAKTERYSTYKA TERMOUTWARDZALNYCH¯YWIC NA PODSTAWIE ESTRU 4-(N-MALEIMIDOFENYLOWEGO) METAKRYLANU HYDROKSYPROPYLOWEGO Streszczenie -Zsyntetyzowano ester 4-(N-maleimidofenylowy) metakrylanu hydroksypropylowego (MPEHPM) w reakcji 4-N-karboksyfenylomaleimidu (CPMI) z metakrylanem glicydylu (GMA) w obecnooeci chlorku trietylobenzyloamoniowego (TEBAC) jako katalizatora. Otrzymany hybrydowy monomer zawieraj¹cy zarówno grupy maleimidowe, jak i metakrylanowe modyfikowano za pomoc¹ bismaleimidu diaminodifenylometanu (MDABMI) b¹dŸ diglicydylowego eteru bisfenolu A (DGEBA) a nastêpnie sieciowano wobec 4,4'-metylenodianiliny (MDA). Obecnooeae w zastosowanym systemie pieroecienia epoksydowego, grup aminowych oraz obydwu typów wi¹zañ podwójnych pozwala na uzyskanie termoutwardzalnego polimeru. Budowê syntezowanych produktów badano metodami FT-IR (rys. 1, 5, 6), 1 H NMR (rys. 2) i 13 C NMR (rys. 3). Proces utwardzania oraz stabilnooeae termiczn¹ usieciowanych zwi¹zków charakteryzowano przy u¿yciu ró¿nicowej kalorymetrii skaningowej (rys. 4, tabela 1) i technik¹ TGA (rys. 7, tabela 2). S³owa kluczowe: ester 4-(N-maleimidofenylowy) metakrylanu hydroksypropylowego, w³aoeciwooeci termiczne, energia aktywacji.High performance thermosets such as epoxy and maleimide resins are of great interest as matrix resins for use in numerous industrial applications, including electrical and electronic industry, car industries, aero and hydrospaces engineering, transporting, etc. because of their unique properties such as: good prelucrability and adherence to different substrates prior to crosslinking, good thermal resistance, superior mechanical and electrical properties and excellent chemical and solvent resistance after crosslinking [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16]. Bismaleimides are attractive materials for the structural adhesives or as resins for matrices, because they can be polymerized under thermal treatment without the elimination of the by-products.The objective of the present work is to report the results of the synthesis and crosslinking polymerization of 4-(N-maleimidophenylester) hydroxypropylmetha-crylate (MPEHPM), a monomer that possesses two polymerizable carbon-carbon double bonds with different reactivities (one of which is the vinylene group of male...