Thermally Crosslinkable and Chemically Modifiable Aromatic Polyesters Possessing Pendant Propargyloxy Groups

Abstract

New aromatic (co)polyesters containing pendant propargyloxy groups were synthesized by phase transfer‐catalyzed interfacial polycondensation of 5‐(propargyloxy)isophthaloyl chloride (P‐IPC) and various compositions of P‐IPC and isophthaloyl chloride with bisphenol A. FTIR and NMR spectroscopic data, respectively, revealed successful incorporation of pendant propargyloxy groups into (co)polyesters and formation of (co)polyesters with desired compositions. (Co)polyesters exhibited good solubility in common organic solvents such as chloroform, dichloromethane, and tetrahydrofuran and could be cast into transparent, flexible, and tough films from chloroform solution. Inherent viscosities and number average molecular weights of (co)polyesters were in the range 0.77–1.33 dL/g and 43,600–118,000 g/mol, respectively, indicating the achievement of reasonably high‐molecular weights. The 10% weight loss temperatures of (co)polyesters were in the range 390–420 °C, demonstrating their good thermal stability. (Co)polyesters exhibited Tg in the range 146–170 °C and Tg values decreased with increase in mol % incorporation of P‐IPC. The study of non‐isothermal curing by DSC indicated thermal crosslinking of (co)polyesters via propargyloxy groups. The utility of pendant propargyloxy group was demonstrated by post‐modification of the selected copolyester with 1‐(4‐azidobutyl)pyrene, 9‐(azidomethyl)anthracene, and azido‐terminated poly(ethyleneglycol) monomethyl ether via copper(I)‐catalyzed Huisgen 1,3‐dipolar cycloaddition reaction. FTIR and 1H NMR spectra confirmed that click reaction was quantitative. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 588–597

Synthesis of aromatic polyesters derived from bisphenol‐A and bis(hydroxyphenyl)butane with diacyl chloride monomers

“…As a type of high-performance special engineering plastic, aromatic polyesters have been widely used in sectors such as industrial production, medical and healthcare, and machinery manufacturing, as well as in daily life. [1][2][3][4][5] A representative aromatic polyester is the commercialized bisphenol-A (BPA) polyarylate. Owing to their highly symmetrical structure, aromatic polyesters exhibit a high molecular chain rigidity, high thermal stability, and excellent mechanical properties.…”

“…As a type of high‐performance special engineering plastic, aromatic polyesters have been widely used in sectors such as industrial production, medical and healthcare, and machinery manufacturing, as well as in daily life 1–5 . A representative aromatic polyester is the commercialized bisphenol‐A (BPA) polyarylate.…”

Synthesis and properties of copolyarylates containing phenol red units

“…The XRD diffraction patterns of the co‐PARs demonstrated a wide halo at 2θ = 10–20°, indicating its amorphous nature. Apparently, the insertion of sulfur‐containing bulky groups hindered the crystallization of the polyarylate and reduced the regularity of the molecular chain, which leads to the formation of amorphous co‐PARs 26–28 …”

Synthesis and Studies on Aromatic Copolyester With Anticancer Activity Derived From 4,4’- Dihydroxybiphenyl and 3,5-Dihydroxytoluene

“…17 Relatively new aromatic copolyesters synthesized from 5-(propargyloxy) isophthaloyl chloride and bisphenol A have displayed 10% weight loss around 400°C validating their superior thermal stability. 18 Analogy between polyesters derived from Terephthaloyl dichloride and Isophthaloyl dichloride along with hindered Biphenols and bulky substituent bearing Hydroquinones has revealed that polyesters obtained from Isophthaloyl dichloride exhibit better solubility and lower glass transition temperatures. 19 High molecular weight crystalline aromatic copolyesters obtained from bisphenols containing pendant, Quinoxaline moiety by polymerization with Isophthaloyl chloride are reported to be thermally stable.…”