A non‐phosgene process to homopolycarbonate and copolycarbonates of isosorbide using dimethyl carbonate: Synthesis, characterization, and properties

Abstract

Poly(isosorbide carbonate) (PIC) was synthesized by melt polycondensation of dimethyl carbonate (DMC) and isosorbide using lithium acetylacetonate (LiAcac) as the catalyst. The reaction conditions were optimized to achieve PIC with relatively high number‐average molecular weight (Mn) of 28,800 g/mol and isosorbide conversion of 95.2%. A series of poly(aliphatic diol‐co‐isosorbide carbonate)s (PAICs) were also synthesized by melt polycondensation of DMC with isosorbide and equimolar amounts of aliphatic diols (1,4‐butanediol, 1,5‐pentanediol, 1,6‐hexanediol, and 1,4‐cyclohexane dimethanol) in the presence of LiAcac and the TiO2/SiO2‐based catalyst (TSP‐44). PAICs with Mn values ranging from 18,700 to 34,400 g/mol and polydispersities between 1.64 and 1.69 were obtained. The 13C NMR analysis revealed the random microstructure of PAICs. The differential scanning calorimetry results demonstrated that all the PAICs were amorphous with a unique Tg ranging from 46 to 88 °C. The dynamic analysis results showed that the incorporation of linear or cyclohexane structure changed the dynamic mechanical properties of PIC drastically. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013

Isosorbide and dimethyl carbonate: a green match

“…Recently DCI has been also prepared via DMC chemistry in the presence of lithium acetylacetonate (Li(acac)) as catalyst [85]. Dicarboxymethyl isosorbide, once formed, has been directly converted into either homo- or co-polycarbonate via an easy straight-forward procedure (Scheme 4).…”

“…Similarly poly(aliphaticdiol- co -isosorbide carbonate)s were prepared via melt polycondensation of DMC with isosorbide and several aliphatic diols employing Li(acac) and the TiO 2 /SiO 2 -based catalyst (Scheme 4) [85]. …”

Partially bio-based polyimides from isohexide-derived diamines

“…8,10 Due to their desirable structural features, isohexides have been extensively investigated as bio-based building blocks for a variety of polymers including polyesters, [12][13] polycarbonates, [14][15] poly (ester amide)s, 16 poly (ester imide)s, 17 polyurethanes, [18][19] and polyethers. 20 The incorporation of isohexides into polymer backbones can lead to several benefits, such as high glass transition temperatures (T g ) and special optical properties.…”

Structural Foams of Biobased Isosorbide-Containing Copolycarbonate

“…Because isosorbide-containing Bio-PC has been on the market for less than five years, most available literature and patents are focused on chemical aspects such as the synthesis of Bio-PC as well as on structural analysis of the polymer [6][7][8][9][10][11]. Only few patents and no detailed scientific investigations concerning foaming and foam properties of Bio-PC were published [12].…”