Abstract
A series of semi-aromatic polyesters named as Poly(PO-CHO-PA) were facilely synthesized via ring-opening terpolymerization of bio-based cyclohexane oxide (CHO)/propylene oxide (PO)/phthalic anhydride (PA) using economical U1/PPNCl as dual catalyst. The proportion of CHO-PA and PO-PA segments in polymer can be readily altered by changing the feed ratio of CHO/PO because the reactivity ratios of CHO and PO with PA calculated by Fineman-Ross method are comparable. All synthesized amorphous polyesters with various compositions show one Tg ranging from 62 °C to 133 °C. Significantly, the mechanical, thermal and barrier properties of these amorphous semi-aromatic polyesters are also adjustable and investigated for the first time. The results indicate the semi-polyesters exhibit superior thermostability (T5% ranging from 306 °C to 323 °C) and high tensile strength (40.21–55.7 MPa) that is comparable with polystyrene (PS). Furthermore, Poly(PO-CHO-PA) films possess a promising prospect as packaging materials because of its colorless and highly transparent nature, along with low oxygen and water vapor transmission rate. All above performances may guarantee its potential alternative to commercial PS.
Highlights
Polyesters are a class of attractive polymers,[1−5] especially the aromatic polyesters constituted by benzoic ester type repeat units, which are widely used as films, fibers, resins, due to their excellent thermal stability and mechanical properties as well as inexpensiveness.[6]
A series of semi-aromatic polyesters named as Poly(PO-CHO-PA) were facilely synthesized via ring-opening terpolymerization of biobased cyclohexane oxide (CHO)/propylene oxide (PO)/phthalic anhydride (PA) using economical U1/PPNCl as dual catalyst
The results indicate the semi-polyesters exhibit superior thermostability (T5% ranging from 306 °C to 323 °C) and high tensile strength (40.21−55.7 MPa) that is comparable with polystyrene (PS)
Summary
Polyesters are a class of attractive polymers,[1−5] especially the aromatic polyesters constituted by benzoic ester type repeat units, which are widely used as films, fibers, resins, due to their excellent thermal stability and mechanical properties as well as inexpensiveness.[6]. Since the middle of the last century, a variety of metal complexes have been developed for ROAC of epoxides and anhydrides.[16,17,24−30] Therein, the cobalt and chromium salen complexes exhibited outstanding catalytic efficiency and selectivity.[16,24,25,27,28,31−33] Most of the polyesters are used as food packaging or sensitive devices, which demand colorless and minimal content of metal element.[1,34,35] there has been a rapidly increasing attention in employing green metal-free catalysts with high activity and selectivity for ROAC of epoxides and anhydrides.[14,36−40] Firstly, organic bases, like quaternary onium salts, tertiary amines, and phosphazene were successively employed as a single catalyst for ROAC, but they did not display satisfactory catalytic efficiency.[14,38−41] Later, Zhang and Li’s group consecutively reported the usage of organoboron compounds/quaternary onium salts in this ROAC process with marvelous activity and stereoselectivity.[37,42] Recently, our group has developed an economical and effective dual organocatalyst, composed of (thio)ureas and organic bases, toward the ROAC of the most commonly used epoxides and anhydrides. A series of polyesters with diverse sequence structures and high ester linkages www.cjps.org link.springer.com
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