Reaction products of parabanic acid and alkylene carbonates as components of polyurethane foams

Abstract

Esteramidoimidotetraols are obtained by reacting 8‐ and 12‐molar excess of ethylene carbonate or propylene carbonate with parabanic acid. The parabanic acid ring undergoes opening, and linear polymeric products are formed. The products can conveniently be used as polyols for polyurethane foams. The results of a study on thermal stability and on compressive strength of foams prepared from these tetraols, measured before and after thermal treatment, are reported. Copyright © 2007 Society of Chemical Industry

Oligomers with structural elements of imidazolidinetrione obtained from oxamic acid and oxamide: polyurethane foams modified by structural elements of imidazolidinetrione

“…The foams obtained by using hydroxypropyl derivatives of parabanic acid [28], urea [31], oxamic acid [26], oxamide [27] and BHPOD [25] exhibited lower water uptake after 24 h at room temperature [34] ( < 9.5 wt%) than the foams obtained by using hydroxyethyl derivatives of the above compounds ( Table 1). The lowest water uptake was the characteristic of the foams obtained by using hydroxypropyl derivatives of oxamide (6 wt% and 4 wt%, Table 1, Nos.…”

“…The resulting rigid foamed polyurethane plastics exhibited glass transition temperatures above room temperature [33], located within the range of 75-145°C [25][26][27][28][29][30][31].…”

“…The hydroxyalkylated derivatives of oxamic acid [26] and oxamide [25,27] as well as parabanic acid [28] and urea [29][30][31] were used as polyol components for the preparation of foamed polyurethane plastics. The influence of the amount of catalyst (triethylamine), isocyanate (4,4′-diisocyanate diphenylmethane with 30 wt% content of triisocyanates), foaming agent (water) and the kind of hydroxyalkyl derivative on the foaming process, has been investigated.…”

“…In the present paper, based on earlier reports [20][21][22][23][24][25][26][27][28][29][30][31], syntheses of the aforementioned oligomers in reactions of oxamic acid and oxamide with alkylene carbonates are described. The applications of oligomers with oxamidoester and oxamide groups, as well as with oxamidoestercarbamidoimide and carbamide groups as polyol components for preparation of thermally stable foamed polyurethane materials are described.…”

Obtaining of polyurethane foams with contribution of hydroxyalkylation products of oxalamide with alkylene carbonates and their properties

“…It was demonstrated in testing of thermal properties of oxamic acid's reaction products (III) [3,4] and carbamide (IV) [5,6] with ACs; structural fragments of these compounds can be distinguished in the structure of hydroxyalkylation products of parabanic acid with alkylene carbonates: (IV) Esteramidoimidotetraols obtained in reactions of parabanic acid with ACs can be used as polyol components for obtaining foamed polyurethane plastics. Rigid polyurethane foams obtained with their contribution are characterized by a slight water uptake, good stability of dimensions, enhanced thermal stability and good compression strength [7]. Similarly, reaction products of oxamic acid and carbamide with ACs can be used for obtaining thermally stable polyurethane foams [5,6,8,9].…”