Synthesis and properties of renewable nonisocyanate polyurethanes (NIPUs) from dimethylcarbonate

Abstract

Novel fully renewable AA-BB type nonisocyanate polyurethanes (NIPUs) were synthesized using the transurethanization approach. Dicarbamate monomers were prepared by the reaction of a diamine with an excess of dimethylcarbonate (DMC), in presence of 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as catalyst. Then, the dicarbamate was reacted with a diol to afford the polymer, in presence of TBD or K 2 CO 3 as catalyst. Several renewable diamines and diols were tested. The two steps were conducted under neat conditions. The obtained Polym. Chem. 2015, 00, 000-000

Synthesis and properties of allyl terminated renewable non-isocyanate polyurethanes (NIPUs) and polyureas (NIPUreas) and study of their photo-crosslinking

“…Three main approaches have been described: (i) The reaction of diamines with five-membered bicyclocarbonates leading to poly(hydroxylurethane)s [4][5][6][7][8][9][10][11][12][13][14][15][16][17]; (ii) the self-polycondensation of AB-type fatty monomers bearing hydroxyl and acyl azide groups, in the presence or absence of catalyst. The heating of acyl azide groups led to in situ formation of isocyanate groups via Curtius rearrangement [18][19][20][21]; (iii) the polycondensation by transurethanization consisting in the reaction between dicarbamates and diols, in the presence of a catalyst, especially 1,5,7-triazabicyclo [4.4.0]dec-5-ene (TBD) [22,23].…”

Flexible and Bio‐Based Nonisocyanate Polyurethane (NIPU) Foams

“…Albeit bio‐based isocyanate resins are available from bio‐based diamines such as pentamethylene diamine, prepared by decarboxylated lysine, they require toxic phosgene to convert amine into isocyanate . In order to avoid special safety, health, and handling precautions and to meet the demands of green chemistry, several approaches aim at the production of nonisocyanate PU (NIPU) without requiring either phosgene or isocyanates . The most prominent members of the NIPU family are polyhydroxyurethanes, produced by polyaddition of multifunctional cyclic carbonates with polyamines .…”

Organocatalytic synthesis of new telechelic polycarbonates and study of their chemical reactivity

“…Furthermore, the presence of both of carbonecarbon double bond and hexyl side chain in PC1-MC disturbed polymer chain organization leading to absence of crystalline domains. This phenomenon has already been observed in the case of polyurethane [22] and polyamide [21] materials based on (9Z)-9-Octadecene-1,12-diol (diol 1) or its corresponding diamine. On the other hand, the linear PC3-MC and PC4-MC were also semi-crystalline with T m values of 30 (second peak at 45 C) and 60 C, respectively; however, their Tg were not observed.…”