Glycerol carbonate methacrylate: A cross-linking agent for hydroxyurethane-acrylate coatings

Abstract

Poly(meth)acrylates are well-known commodity polymers widely used for coating applications due to easy production, low cost and interesting properties such as their relatively high thermal stability, resistance to breakage and transparency. Some of these properties can be improved by cross-linking, therefore an additional functionalization is necessary. Carbonate group allowed reaction with amines to generate a urethane linkage without the use of toxic and harmful isocyanates. We have synthesized (meth)acrylic copolymers functionalized with cyclic carbonates groups using butyl acrylate (BA), methyl methacrylate (MMA) and glycerol carbonate methacrylate (GCMA) as comonomers to obtain cross-linkable polymers. Different ratios of BA and MMA have been used in order to evaluate the effect on the thermomechanical properties. The cross-linking was performed with tris(2-aminoethyl)amine at 80°C during 2h and was quantitative. The cross-linked hydroxyurethane acrylate copolymers were fully characterized and were used as coatings on glass and steel. The ease of the application and curing process as well as the adhesion strength tests showed that these cross-linked copolymers are promising materials as coating on glass and steel.

Poly(hydroxyurethane) Adhesives and Coatings: State-of-the-Art and Future Directions

“…71 Coatings derived from 40/60 w/w [VEC]/[VV9] were glossy and resistant to MEK but displayed poor impact resistance as a result of high cross-linking density. Recently, Morales-Cerrada et al 72 carried out the copolymerization of butyl acrylate, methyl methacrylate, and glycerol carbonate methacrylate for hydroxyurethane-acrylate coatings (Scheme 3a). The copolymers were dissolved in MEK and mixed with tris(2-aminoethyl)amine and cured at 80 °C for 2 h. The cross-linked materials presented high adhesion to stainless and glass.…”

The effect of polyhedral oligomeric silsesquioxane fillers in non‐isocyanate polyurethane hybrid resins

“…Similarly, studies that focused on silicones applied siloxane‐containing monomers, 29,30 polyhedral oligomeric silsesquioxanes (POSS), 30–35 and sol–gel methods 36–39 . Finally, acrylic‐based routes for HPHU synthesis employed amine terminated PHU prepolymers, 40–43 hydroxyurethane methacrylates, 44–47 and pendant cyclic carbonate functional prepolymers 48–52 . In addition to these routes, other hybrid approaches have been particularly applied with waterborne HPHUs 53–55 which have been reviewed recently 56–58 .…”

“…[36][37][38][39] Finally, acrylic-based routes for HPHU synthesis employed amine terminated PHU prepolymers, [40][41][42][43] hydroxyurethane methacrylates, [44][45][46][47] and pendant cyclic carbonate functional prepolymers. [48][49][50][51][52] In addition to these routes, other hybrid approaches have been particularly applied with waterborne HPHUs [53][54][55] which have been reviewed recently. [56][57][58] Namely, these routes are hybrids in that the urethanes are functionalized and hybridized, for example, with monomers employing free radical polymerization methods.…”

Fabrication of novel buckypaper metal oxide nano-catalysis glycerol carbonate/MWCNTs membrane for efficient removal of heavy metals

“…These reactive sites open up a wide range of possibilities for employing glycerol carbonate as a raw material for converting chemical intermediates into surfactants and polymers. This is an indirect method of synthesizing polymers for application in coatings, adhesives, foams, and other materials [ 36 , 37 ]. The objective view of this study is the fabrication of a novel membrane buckypaper metal oxide nano-catalysis glycerol carbonate/MWCNTs membrane for the efficient removal of heavy metals from wastewater.…”