Propylene carbonate as a source of carbonate units in the synthesis of elastomeric poly(carbonate–urethane)s and poly(ester–carbonate–urethane)s

Abstract

The synthesis of oligocarbonate diols from propylene carbonate (PC) and α,ω‐diols with hydrocarbon chain of various length is presented and discussed. Syntheses with different catalysts and molar ratio of the reactants were performed. Novel method of the synthesis of oligo(ester–carbonate) diols based on PC, dimethyl succinate, adipate or terephthalate, and α,ω‐diols was investigated. The resultant oligomerols did not contain any oxy‐1,2‐propylene fragments as well as other ether units in their chemical structure. Based on the obtained oligocarbonate and oligo(ester–carbonate) diols, polyurethanes were obtained according to the prepolymer method using isophorone and hexamethylene diisocyanate and water as a chain extender. The obtained products exhibited very good mechanical properties—tensile strength up to 50 MPa with 425% elongation at break [for PUR based on oligo(tetramethylene carbonate) diol] and 45 MPa, 625% [for (oligo(tetramethylene succinate‐co‐carbonate)diol with 44 mol % of carbonate units]. © 2013 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2014, 131, 39764.

Aliphatic-aromatic poly(ester-carbonate)s obtained from simple carbonate esters, α,ω-aliphatic diols and dimethyl terephthalate

“…695.91 g of poly(tetramethylene terephthalate-co-carbonate) as a white solid with M n = 24 790 and 46 mol.% of carbonate units was obtained. Poly(tetramethylene terephthalate-co-carbonate) was alternatively obtained from propylene carbonate as a source of carbonate linkages according to the procedure described by us earlier [37].…”

“…The reaction was carried out in an azeotropic solvent (n-heptane) [9,37], so the by-product (1,2-propylene glycol) was removed from the reaction mixture as an hetero-azeotrope. The attempts of removing of 1,2-propylene glycol by distillation failed due to its co-distillation together with 1,4-butanediol.…”

PET wastes utilization in the synthesis of aliphatic–aromatic polyurethane elastomers

“…FTIR spectra were recorded on a Biorad FTS-165 FTIR spectrometer as KBr pellets. 1 H NMR spectra were recorded at room temperature on Varian VXR 400-MHz spectrometer using tetramethylsilane as an internal reference and CDCl 3 or mixture of CDCl 3 and d-trifluoroacetic acid as solvent and analyzed with MestReNovav.6.2.0-7238 (Mestrelab Research S.L) software. The carbonate unit content in the copolymers was calculated from 1 H NMR spectra according to our earlier report.…”

“…In all the investigated samples, the tensile strength was improved in comparison to that of poly(carbonate-urethane)s without aromatic units in soft segments ( Table 6, runs 1, 8, 14, and 18). [1,38] CONCLUSIONS A new method of transformation of PET waste into various oligo (alkylene terephthalate)s in the alcoholysis process carried out with the use of azeotropic distillation of ethylene glycol was described and discussed. The synthesis of aromatic-aliphatic oligomerols based on oligo(alkylene terephthalate)s and DMC as a source of carbonate units was performed efficiently.…”

“…The soft segments in PUR elastomers mostly consist of ester, ether and carbonate aliphatic oligomerols. Oligocarbonate diols, due to the presence of carbonate linkages in the main chains, exhibit a much greater resistance to hydrolysis in comparison with oligoestrols and to oxidation in comparison to their ether analogues . Moreover, polyurethanes based on carbonate oligomerols are characterized by high elasticity and mechanical strength.…”