Novel Thermally Stable Poly(sulfone ether ester amide)s with Improved Solubility

Abstract

A three-step method was used to prepare a novel sulfone ether ester diamine. In the first step, reaction of 1,5-dihydroxy naphthalene with 4- nitrobenzoyl chloride afforded 5-hydroxy-1-naphthyl-4-nitrobenzoate (HNNB). By reduction of nitro group, an amino compound named 5-hydroxyl-1-naphthyl- 4-aminobenzoate (HNAB) was obtained. Reaction of HNAB (two moles) with bis (4-chlorophenyl) sulfone resulted in preparation of a novel sulfone ether ester diamine (SEED). Polycondensation reactions of the diamine with aromatic and aliphatic diacid chlorides led to preparation of new poly(sulfone ether ester amide)s. Conventional methods were used to characterize the structure of the monomer and polymers. Physical properties of the polymers were also studied. The polyamides were thermally stable and they showed improved solubility in dipolar aprotic solvents.

Synthesis and properties of hyperbranched polyimides derived from novel triamine with prolonged chain segments

“…Although soluble polyimides can be obtained from ether‐containing monomers, as is well known, introduction of flexible groups to the polyimide backbones will sacrifice their thermal stability and mechanical properties . It has been proved that introduction of rigid heteroaromatic pyridine ring to the polymer backbone could endow it excellent thermal stability, which should be useful to decrease the negative effects resulted from the introduction of flexible ether linkages in the polyimides backbone . Furthermore, polysubstituted pyridine derivatives, especially the symmetrical triarylsubstituted pyridine compounds are not only important medicine structural units, but also key intermediates of the synthesis of complex organics.…”

“…[16][17][18] It has been proved that introduction of rigid heteroaromatic pyridine ring to the polymer backbone could endow it excellent thermal stability, which should be useful to decrease the negative effects resulted from the introduction of flexible ether linkages in the polyimides backbone. [19][20][21] Furthermore, polysubstituted pyridine derivatives, especially the symmetrical triarylsubstituted pyridine compounds are not only important medicine structural units, but also key intermediates of the synthesis of complex organics. They present favorable physiological activity.…”

New Polyimide and Nanoporous Structures with Low Dielectric Constant

“…Among several methods for the preparation of low dielectric constant polyimides, introducing nanometric porosity into the polymer films is one of the best methods due to some advantages such as low dielectric constant and good solubility without sacrifice of their thermal and mechanical properties. [22][23][24][25][26] In this research, a pyridine-based aromatic diamine bearing ether and amide groups was synthesized and used to produce polyimide nanofoams. As shown in Scheme 1, the diamine monomer was synthesized in two steps via nucleophilic substitution reactions.…”

“…For comparison, it should be mentioned that while the dielectric constant of Kapton (as a common nonfluorinated polyimide) is about 3.67-3.89 and also most of fluorinated polyimides are in the range of 2.60-3.33, the dielectric constant of polyimide nanofoams is about 2.30-2.60, presenting the efficiency of the nanofoam method in reducing the dielectric constant of polyimides. 22,23,[28][29][30][31][32] The morphology and microstructure of nanofoams were characterized by SEM and TEM. As it was observed from micrographs, the size of pores was in the range of 35-70 nm and most of the pores existed in the form of closed cells.…”

Soluble, thermally stable poly(amide-ester)s containing pyridine pendent group

“…Another suitable way for modification of polymer properties is copolycondensation, for instance modification of the properties of polyesters by incorporation of hydrogenbonded amide groups or imide units produces copolymers with modified properties [7][8][9][10][11][12][13][14][15][16][17]. In recent years there has been a growing interest in poly(amide-ester)s because of their expected degradable, thermal and mechanical properties.…”