Synthesis and characterization of new soluble poly(ester‐imide)s containing noncoplanar 2,2′‐dimethyl‐4,4′‐biphenylene unit

Abstract

ABSTRACT:A new diimide-diacid chloride (3) containing a noncoplanar 2,2Ј-dimethyl-4,4Ј-biphenylene unit was synthesized by treating 2,2Ј-dimethyl-4,4Ј-diamino-biphenylene with trimellitic anhydride followed by refluxing with thionyl chloride. Various new poly(ester-imide)s were prepared from 3 with different bisphenols by solution polycondensation in nitrobenzene using pyridine as hydrogen chloride quencher at 170°C. Inherent viscosities of the poly(esterimide)s were found to range between 0.31 and 0.35 dL g Ϫ1 . All of the poly(ester-imide)s, except the one containing pendent adamantyl group 5e, exhibited excellent solubility in the following solvents: N, N-dimethylformamide, tetrahydrofuran, tetrachloroethane, dimethyl sulfoxide, N,N-dimethylacetamide, N-methyl-2-pyrrolidinone, m-cresol, o-chlorophenol, and chloroform. The polymers showed glass-transition temperatures between 166 and 226°C. The 10% weight loss temperatures of the poly(ester-imide)s, measured by TGA, were found to be in the range between 415 and 456°C in nitrogen.

Poly(ester imide)s Possessing Low CTE and Low Water Absorption (II). Effect of Substituents

“…The non-substituted TAHQ/4,4 0 -ODA system showed a high T g at 340 C with a broad transition around 210 C in the DMTA curve (this lower temperature transition will be discussed later). The results revealed that the effect of the methoxy and methyl substituents caused a certain degree of T g increase (20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30) C) as shown in Table III. This can be interpreted in terms of suppressed internal rotation of the central hydroquinone moiety by some steric hindrance due to the present small substituents.…”

“…We previously proposed a hybrid material between PIs and polyesters, namely, poly(ester imide)s (PEsIs) as a new material for FCCL and our results revealed that some PEsIs derived from TAHQ with APAB and a minor fraction of a flexible diamine as a comonomers achieved a very low extent of water absorption, a low CTE value approximate to copper foil, and excellent flexibility (film toughness) at the same time. 19 Poly(ester imide)s have been so far studied only in the limited view points of film basic properties such as thermal stability and solubility, and mechanical properties, [20][21][22][23][24][25][26] mechanical properties of fibers, 27 liquid crystallinity [28][29][30] without any attentions toward FCCL applications. Many of the previously reported poly(ester imide)s were synthesized via the direct polymerization of polyester from imide-containing diols with dicarboxylic acids without the pathway of thermal imidization which plays a great role for spontaneous in-plane orientation.…”

A facile approach towards functionalization of MWCNTs with vitamin B2 for reinforcing of biodegradable and chiral poly(ester-imide) having L-phenylalanine linkages: morphological and thermal investigations

“…These are extensively used in membranes, adhesives, engineering thermoplastics, printed circuit boards, and electronic devices [25][26][27].…”

Efficient surface modification of MWCNTs with vitamin B1 and production of poly(ester-imide)/MWCNTs nanocomposites containing L-phenylalanine moiety: Thermal and microscopic study

“…This class of polymers brings together the desirable characteristics from both polyesters and polyimides. These properties make them suitable for different applications in printed circuit boards, engineering thermoplastics, electronic devices, membranes, and adhesives, [19][20][21] being a promising matrix candidate for hybrid materials. In this paper, the attaching of thiamine hydrochloride (vitamin B 1 ) on carboxylated-multi-walled carbon nanotubes (MWCNTs-COOH) was carried out under ultrasonic irradiation.…”