Polyetherols from isocyanuric acid and ethylene carbonate

Abstract

ABSTRACT:A new method of preparation of polyetherols containing perhydro-1,3,5-triazine rings from isocyanuric acid and an excess of ethylene carbonate was developed. The course of reaction was studied at various molar ratios of reagents. The structure of the products was established, and some physical properties were measured.

Synthesis of polyetherols with isocyanuric ring. Kinetics and mechanisms of reactions, part 2: Consecutive reaction of ethylene carbonate with isocyanuric acid

“…Already in this system, low-intensity resonances at 4.4-4.9 ppm from terminal O CH 2 CH 2 OH groups of consecutive products were observed. Their intensity increases at the spectra of further products of the reaction between IA and EC [5]. Because the percentage of oxyethylene groups in the product is known from the mass balance, the number of unreacted imide groups and N-(2-hydroxyethyl) groups in intermediates can be estimated from 1 H NMR spectra.…”

Polyetherols from isocyanuric acid and propylene carbonate

“…7 The percentage of unreacted propylene carbonate (p PC ) was calculated from the following equation:…”

“…DABCO and other ternary amines catalyze mostly the formation of imide anions [11][12][13][14] (7) and alcoholates to a lesser extent: (8) TBAH plays an ambivalent role: (1) it enables the formation of imide anions due to the presence of OH groups [eq. (3)], and (2) it facilitates the formation of alcoholates because of the decomposition of TBAH at elevated temperatures to tributylamine, which plays the same role as DABCO shown in eq.…”

“…For instance, resin products were formed at IA-PC ϭ 1 : 3, whereas the use of EC instead of PC led to solid 1,3,5-tris(2-hydroxyethyl isocyanurate). 7 For the system IA-PC ϭ 1: 2.4, a mixture of solid (0.12% w/w) and resin products was obtained. The acid number of the latter was 26 mg of KOH/g, which pointed to the presence of unreacted imide groups, which was confirmed by the 1 H-NMR spectrum.…”

“…One can avoid this disadvantage by using alkylene carbonates, as demonstrated in ref. 7 by the one-step synthesis of polyetherols from IA and ethylene carbonate (EC) according to the following equation: (1) where n is the number of oxyalkylene groups in the product. EC played the roles of both reagent and solvent.…”