Solubility in CO2 and carbonation studies of epoxidized fatty acid diesters: towards novel precursors for polyurethane synthesis

How to explain low molar masses in PolyHydroxyUrethanes (PHUs)

“…This compound 19 was selected because it has no ester bonds, which could have introduced additional side-reactions [19,24]. The formation of amide groups can indeed be observed when reacting primary aliphatic amines, or even cycloaliphatic amines with compounds bearing ester groups such as vegetable oils for instance [35,36].…”

“…PHUs are an interesting class of polymers based on the formation of 2-hydroxyurethane bonds by the reaction between cyclic carbonates and amines [8][9][10]. Both the scientific and industrial communities are taking more and more interest in such PHUs as well as in non-hazardous and biobased cyclic carbonates [11][12][13][14][15][16][17][18][19][20].…”

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

“…These diesters can be epoxidized, and then carbonated and, subsequently, reacted with diamines to generate linear PHUs. 18 Although substantial progress has been made on the synthesis of PHUs from vegetable oils, the problems related to their potential competition with food production remain a concern.…”

“…However, the uncontrolled functionality and varied structures of vegetable oils sometimes result in illdened networks of the resulting cross-linked PHUs. 17,18 For this reason, several attempts have been made to synthesize linear PHUs from vegetable oils. For example, unsaturated fatty acid diesters can be obtained by the transesterication of vegetable oils with diols.…”

Recent Advances in Vegetable Oil‐Based Polyurethanes

“…[66] The two bis-carbonates, internal carbonated fatty acid diester (ICFAD) and terminal carbonated fatty acid diester (TCFAD), were derived from oleic acid methyl ester (Scheme 13). The TPUs formed had molecular weights up to 13,500 g mol À1 and exhibited relatively low T g values.…”