Synthesis and characterization of polyesters based on 1,1,1‐[bis(4‐hydroxyphenyl)‐4′‐pentadecylphenyl]ethane

Abstract

Aromatic polyesters are of considerable interest because of their excellent mechanical properties, chemical resistance and thermal stability. However, most aromatic polyesters are difficult to process due to their high glass transition temperatures coupled with their insolubility in common organic solvents. The present article describes a series of organosoluble polyesters and copolyesters based on 1,1,1‐[bis(4‐hydroxyphenyl)‐4′‐pentadecylphenyl]ethane. A series of new aromatic polyesters containing pendant pentadecyl chains was synthesized by interfacial polycondensation of 1,1,1‐[bis(4‐hydroxyphenyl)‐4′‐pentadecylphenyl]ethane with terephthalic acid chloride (TPC), isophthalic acid chloride (IPC) and a mixture of TPC and IPC. A series of copolyesters was synthesized from 4,4′‐isopropylidenediphenol with TPC by incorporating 1,1,1‐[bis(4‐hydroxyphenyl)‐4′‐pentadecylphenyl]ethane as a comonomer. Inherent viscosities of the polyesters and copolyesters were in the range 0.72–1.65 dL g−1 and number‐average molecular weights were in the range 18 170–87 220. The polyesters and copolyesters containing pendant pentadecyl chains dissolved readily in organic solvents such as chloroform, dichloromethane, pyridine and m‐cresol and could be cast into transparent, flexible and apparently tough films. Wide‐angle X‐ray diffraction data revealed the amorphous nature of the polyesters and copolyesters. The formation of loosely developed layered structure was observed due to the packing of pendant pentadecyl chains. The temperature at 10% weight loss, determined using thermogravimetric analysis in nitrogen atmosphere, of the polyesters and copolyesters containing pendant pentadecyl chains was in the range 400–460 °C. The polyesters and copolyesters exhibited glass transition temperatures in the range 63–82 °C and 177–183 °C, respectively. Copyright © 2010 Society of Chemical Industry

Synthesis and characterization of organo‐soluble poly(ether ether ketone)s and poly(ether ether ketone ketone)s containing pendant pentadecyl chains

“…The bisphenol monomers viz ; 1,1,1‐[bis(4‐hydroxyphenyl)‐4′‐pentadecylphenyl]ethane (BHPE) and 1,1‐bis(4‐hydroxyphenyl)‐3‐pentadecylcyclohexane (BHPC) were synthesized starting from cashewnut shell liquid (CNSL) using procedure described in our previous work. 34, 37, 39, 40 The 4,4′‐difluorobenzophenone (DFB) and 1,3‐bis(4‐fluorobenzoyl)benzene (BFB) (Aldrich, USA) were recrystallized from toluene before use. Anhydrous potassium carbonate (S.D.…”

“…Recently, we have reported a series of difunctional monomers containing pendant pentadecyl chain which were utilized for the synthesis of high performance polymers such as aromatic polyesters, polyamides, poly(amideimide)s, and polyimides. 34–38 It was demonstrated that the presence of pendant pentadecyl chains improved the solubility and processability of these polymers and provided a large temperature difference between the glass transition temperature and the initial decomposition temperature. In continuation of our ongoing‐efforts to synthesize processable high performance polymers, we wish to report herein synthesis of poly(ether ether ketone)s (PEEKs) and poly(ether ether ketone ketone)s (PEEKKs) containing pendant pentadecyl chains by nucleophilic polycondensation of each of the two bisphenols viz , 1,1,1‐[bis(4‐hydroxyphenyl)‐4′‐pentadecylphenyl]ethane (BHPE) and 1,1‐bis(4‐hydroxyphenyl)‐3‐pentadecyl cyclohexane (BHPC) with commercially available aromatic dihalide monomers viz ; 4,4′‐difluorobenzophenone (DFB) and 1,3‐bis(4‐fluorobenzoyl)benzene (BFB).…”

New poly(1,3,4‐oxadiazole)s bearing pentadecyl side chains: Synthesis and characterization

“…It is generally known that polymers having long flexible side chains crystallize into layered structures in which the main chains come together to form backbone layers and the side chains to form a separate crystal region 31–35, 38, 43–45. X‐ray diffractograms of polyhydrazides and poly(1,3,4‐oxadiazole)s displayed presence of sharp reflection peak in the small‐angle region at around 2θ = ∼ 3°.…”

“…Recently, we have reported a series of soluble and processable high performance polymers containing pendant pentadecyl chains starting from (CNSL). It was demonstrated that, the pentadecyl chains acts as an internal plasticizers and hence aids in improved processability and simultaneously imparts the solubility characteristics to the resulting polymer 33–38. In continuation with our ongoing efforts to obtain polymers with improved solubility, we wish to report herein synthesis of a series of new poly(1,3,4‐oxadiazole)s containing flexibilizing ether linkages and pentadecyl side chains.…”

Processable aromatic polyesters based on bisphenol derived from cashew nut shell liquid: synthesis and characterization

“…Continuing with our efforts towards processable high performance polymers containing pentadecyl chains, [22][23][24][25][26][27][28][29][30] we report herein the synthesis of a new bisphenol, viz., 4-(4-hydroxyphenoxy)-3-pentadecylphenol (HPPDP) starting from cashew nut shell liquid (CNSL). We also report the interfacial polycondensation of HPPDP with terephthalic acid chloride (TPC), isophthalic acid chloride (IPC) and a mixture of TPC and IPC (50:50 mol %) to form a series of polyesters.…”