Alternating Copolymerization of Propylene Oxide and Cyclohexene Oxide with Tricyclic Anhydrides: Access to Partially Renewable Aliphatic Polyesters with High Glass Transition Temperatures

Sanford, Maria J.; Carrodeguas, Leticia Peña; Zee, Nathan J. Van; Kleij, Arjan W.; Coates, Geoffrey W.

doi:10.1021/acs.macromol.6b01425

Cited by 132 publications

(161 citation statements)

References 68 publications

Supporting

Mentioning

154

Contrasting

Order By: Relevance

“…[1,2] In the last decade,v arious catalyst systems have been developed for this transformation. [3][4][5][6][7][8][9] A variety of epoxides and anhydrides have been reported as monomers,w hich has resulted in the discovery of more than 400 new structural polymers with aw ide range of glass transition temperatures (T g )ofÀ29 to 184 8 8C. [1] In some cases, regio-and/or stereoselective copolymerization was achieved, thereby affording stereoregular polyesters with enhanced thermal stability.…”

mentioning

confidence: 99%

Reversible Transformation between Amorphous and Crystalline States of Unsaturated Polyesters by Cis–Trans Isomerization

et al. 2019

View full text Add to dashboard Cite

An aliphatic polyester has been prepared from ethylene oxide and maleic anhydride that undergoes reversible transformation between amorphous (T g = 18 8 8C) and crystalline (T m = 124 8 8C) states through cis-trans isomerization of the C=Cb onds in the polymer backbone without any change in either the molecular weight or dispersity of the polymer.A similar transformation was also observed in chiral unsaturated polyesters formed from enantiopure terminal epoxides,such as epichlorohydrin, phenyl glycidyl ether,and (2,3-epoxypropyl)benzene. These unsaturated polyesters with 100 %E -configuration in the crystalline state were prepared by quantitative isomerization of their Z-configuration analogues in the presence of ac atalytic amount of diethylamine,w hile in the presence of benzophenone,i rradiation with 365 nm UV light resulted in the transformation of about 30 %t rans-alkene to cis-maleate form, thereby affording amorphous polyesters.

show abstract

mentioning

confidence: 99%

Reversible Transformation between Amorphous and Crystalline States of Unsaturated Polyesters by Cis–Trans Isomerization

et al. 2019

View full text Add to dashboard Cite

show abstract

“…This was also observed for (thiolfan*)Al(O t Bu) for the polymerizations of CL, VL, and TMC, for which DFT calculations revealed a lower activation barrier for the propagation steps over initiation. [8h] With cyclohexene oxide, only the oxidized state was active ( Table 1, entries [13][14][15][16][17]. 100 equivalents of cyclohexene oxide polymerized readily within minutes at room temperature, but the polymer was difficult to isolate.…”

Section: Resultsmentioning

confidence: 99%

Switchable Ring‐Opening Polymerization by a Ferrocene Supported Aluminum Complex

2019

View full text Add to dashboard Cite

An aluminum(III) iso‐propoxide complex supported by salfen (1, salfen=1,1′‐di(2,4‐bis‐tert‐butyl‐salicylimino)ferrocene) was synthesized and characterized. Compound 1 can be reversibly oxidized and reduced, and both redox species were surveyed as ring‐opening polymerization catalysts for cyclic esters and cyclohexene oxide. Based on the observed reactivity behavior, 1 could be used as a redox‐switchable catalyst for the formation of AB and ABC type di‐ and triblock copolymers of lactide, cyclohexene oxide, and trimethylene carbonate.

show abstract

“…prepared new polyesters from propylene oxide (PO) or CHO with those anhydrides. The resultant polyesters had a broad range of T g values from 66 to 184 °C, and the T g value of 184 °C was the highest value reported for aliphatic polyesters . Williams et al.…”

Section: Introductionmentioning

confidence: 97%

Preparation and Thermal Properties of Polycarbonates/esters Catalyzed by Using Dinuclear Salph‐Al from Ring‐Opening Polymerization of Epoxide Monomers

Zhou

Duan

et al. 2017

Chemistry An Asian Journal

View full text Add to dashboard Cite

A dinuclear Salph-Al complex/bis(triphenylphosphine)iminium chloride catalyst system was synthesized and employed for cyclohexene oxide (CHO) and CO copolymerization. The catalyst system had an excellent selectivity of 99 % for carbonate linkages and the resultant poly(cyclohexene carbonate) (PCHC) had a high glass transition temperature (T ) of 123.8 °C and a thermal decomposition temperature (5 % weight loss; T ) of 265 °C. Furthermore, this catalyst system was active in the polymerization of phthalic anhydride (PA) and epoxides. Poly(CHO-alt-PA) was completely alternating, and had improved thermal properties (T =142.7 and T =295 °C) compared with PCHC. The T values of the polyesters could be adjusted by addition of PO to the CHO/PA reaction system. For the CHO/PO/PA terpolymerization, CHO and PO participated concurrently and proportionally in the chain growth and the obtained terpolyesters had tunable T values from 62.8 to 142.7 °C depending on the CHO/PO feed ratio.

show abstract

Alternating Copolymerization of Propylene Oxide and Cyclohexene Oxide with Tricyclic Anhydrides: Access to Partially Renewable Aliphatic Polyesters with High Glass Transition Temperatures

Cited by 132 publications

References 68 publications

Reversible Transformation between Amorphous and Crystalline States of Unsaturated Polyesters by Cis–Trans Isomerization

Reversible Transformation between Amorphous and Crystalline States of Unsaturated Polyesters by Cis–Trans Isomerization

Switchable Ring‐Opening Polymerization by a Ferrocene Supported Aluminum Complex

Preparation and Thermal Properties of Polycarbonates/esters Catalyzed by Using Dinuclear Salph‐Al from Ring‐Opening Polymerization of Epoxide Monomers

Contact Info

Product

Resources

About