Polyurethanes with Pendant Hydroxyl Groups: Synthesis and Characterization

Abstract

Communication: Phenoxycarbonyloxymethyl ethylene carbonate 4 was synthesized from glycerol carbonate and phenyl chloroformate. Polyurethanes with pendant hydroxyl groups were obtained from polycondensation reactions of this AA* monomer with diamines. These polymers contain primary as well as secondary hydroxyl groups. The obtained polyurethanes are amorphous materials. The glass transition temperature decreases with increasing number of methylene groups between the urethane groups.

A novel 2,5-furandicarboxylic acid-based bis(cyclic carbonate) for the synthesis of biobased non-isocyanate polyurethanes

“…Most studies agreed that the high molecular exibility between the hydroxyurethane groups led to lower T g of PHUs. 1,28,30,34,35 The octamethylene moiety of the 1,8-diaminooctane-based PHUs should have higher exi-bility of the polymer chains than the hexamethylene moiety of the 1,6-hexanediamine-based ones. However, the PHUs synthesized from 1,8-diaminooctane showed similar T g compared to those synthesized from 1,6-hexanediamine.…”

Synthesis and characterization of functional six-membered ring carbonates for the preparation of orthogonal couplers

“…Commonly six-membered ring carbonates are used as monomers for the preparation of polycarbonates and poly(hydroxyurethane)s [9,10,12,[17][18][19][20][21]. To our knowledge this class of compounds was not used before as couplers for the connection of different building blocks.…”

“…(ii) However, reaction with the second amine leads to a mixture of two isomeric compounds as a result of the non-selective opening of the substituted five-membered ring carbonate [8][9][10]. The consequence of this are different properties in self-association and different reactivity of the resulting alcohol group.…”

“…A further example is the relative order of reactivity for acid catalysed hydrolysis, which is 6-> 5-> 7-membered ring carbonate. [16] Six-membered ring carbonates are commonly used for the preparation of poly(carbonate)s [12,[17][18][19] and poly(hydroxy urethane)s [9,10,20,21] …”

Lanthanum Oxide-catalyzed Transesterification of Dimethyl Carbonate with Glycerol: Effect of Surfactant

“…19 Glycerol carbonate (GLC) is a valuable glycerol derivative due to its potential application as a membrane component for gas separation, as a component of coatings and detergents, and as a monomer of polycarbonate and polyurethane. [20][21][22][23][24] Among the various glycerol carbonate synthetic routes such as direct reaction of glycerol and CO 2 , 25 glycerolysis of urea, [26][27][28] and oxidative carbonlyation of glycerol, 29 transesterification of dimethyl carbonate (DMC) with glycerol (Scheme 1) is preferable in terms of mild reaction conditions and high glycerol carbonate yield.…”