Michael addition curable coatings from renewable resources with enhanced adhesion performance

Abstract

Novel malonate-functional polyesters from biobased and potentially biobased monomers were developed and cured through the base-catalyzed carbon-Michael addition reaction with acryloyl-functional oligomers. Both drop-in monomers, such as fully biobased diethyl malonate, and alternative raw materials, such as isosorbide and vegetable oil, were introduced. Isosorbide-based polyesters show improved performance to humidity in terms of adhesion on epoxy-amine primer, while vegetable oil-containing resins lead to improved coating appearance due to better flow and levelling. This study demonstrates that biobased malonate resins, having renewable contents up to 53%, offer attractive performance benefits in 2K RMA paints. It is anticipated that, with the development of additional fully biobased polyols, renewable contents in excess of 80% can be achieved.

Poly(ether)s derived from oxa-Michael polymerization: a comprehensive review

“…However, in polymer chemistry the oxa-Michael reaction has received less attention so far. Instead, academic as well as industrial researchers have focused on other Michael variants, namely aza-Michael [11][12][13][14], carba-Michael [14][15][16], and thia-Michael [14,[17][18][19][20] polymerization in which amines, CH-acidic compounds, and thiols are used as donors, respectively. The dominance of these Michael variants can be explained by the higher reactivity of the donors allowing for a relatively easy preparation of a large variety of polymers.…”

Poly(ether)s derived from oxa-Michael polymerization - A comprehensive review

“…[7][8][9] However, in polymer chemistry the oxa-Michael reaction has received less attention so far. Instead, academic as well as industrial researchers have focused on other Michael variants, namely aza-Michael [10][11][12][13], carba-Michael [13][14][15] and thia-Michael [13,[16][17][18][19] polymerization in which amines, CH-acidic compounds and thiols are used as donors, respectively. The dominance of these Michael variants can be explained by the higher reactivity of the donors allowing for a relatively easy preparation of a large variety of polymers.…”

Synthesis of polyester thermosets via internally catalyzed Michael-addition of methylene compounds on a 2-(trifluoromethyl)acrylate-derived building block

“…15 Crosslinked networks were also synthesized by thia-Michael [16][17][18][19][20][21][22] and aza-Michael [23][24][25] and some of these networks also demonstrated reprocessability under thermal stimulus via Michael exchange. [26][27][28] While Michael addition of active methylene compounds on acrylate enabled the synthesis of some crosslinked networks under catalyzed or UV-promoted conditions, [29][30][31][32] no crosslinked network based on a catalyst-free bis-carbon-Michael addition has been described to the best of our knowledge, although the use of this reaction should allow the preparation of useful materials.…”