The preparation of perfectly alternating poly(amide-imide)s via amide unit containing new diamine

Abstract

The synthesis of N,N′‐bis(4′‐amino‐4‐biphenylene) isophthalamide (BABPI) and its applicability as a new diamine for the preparation of a series of new, high Tg, perfectly alternating poly(amide‐imide)s is described. BABPI was synthesized from the catalytic reduction of the corresponding dinitro compound which was prepared by the condensation of isophthaloyl chloride and 4‐amino‐4′‐nitrobiphenyl. The modified selective reduction technique was used for the preparation of 4‐amino‐4′‐nitrobiphenyl from 4,4′‐dinitro‐biphenyl. Poly(amide‐imide)s were synthesized by polycondensation of diamine BABPI with various commercially available aromatic dianhydrides via a conventional two‐step procedure. In the first step, poly(amic‐acid)s were prepared in a polar aprotic solvent, such as N‐methyl pyrrolidone (NMP) at room temperature. Depending on the dianhydride used, intrinsic viscosities of poly(amic‐acid)s were found to range between 0.43–0.69 dL/g. Bulk thermal imidization technique was used to obtain fully imidized poly(amide‐imide)s at the second step. The synthesized poly(amide‐imide)s showed good thermal stability up to 320°C and the 10% weight loss temperatures were recorded in the range of 525–550°C as evidenced by thermogravimetric analysis (TGA). The glass transition temperatures were found to be between 225–235°C from differential scanning calorimeter (DSC) measurements. © 1997 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 35: 1149–1155, 1997

Synthesis of Novel Thermostable Polyamideimides from Bis(2-aminoethyl)terephthalamide and Dianhydrides

“…Another series of PAIs was prepared from an aromatic amide-containing diamine, N , N ′-bis­(4′-amino-4-biphenylene)­isophthalamide, and PMDA, BTDA, or OPDA by the bulk thermal imidization of AAs. The XRD patterns of these PAIs showed broad peaks at 2θ = 20° or d = 4.4 Å.…”

“…Some key methods are used to prepare PAI: (i) condensation of an imide-containing diacid with a diamine, − (ii) condensation of an amide-containing diamine with a dianhydride, − and (iii) thermal imidization of a polyamide–amic acid (AA) …”

“…This diamine was prepared by the aminolysis of waste poly(ethylene terephthalate) (PET) bottles with ethylenediamine. 26 This is a short and cost-effective approach to prepare an amide-containing diamine compared to the two-step 22 or four-step 23 methods from monomers.…”

Synthesis of Aromatic Conjugated Main Chain Azobenzene Polymers and Their Properties

“…Syntheses were performed according to the literature [13]. Nitroamine products 4-amino-4′-nitro biphenyl 1, 4-amino-4′-nitro-biphenyl ether 2 were obtained.…”

Soluble Poly(amide-imide)s from Diamide–Diamine Monomer with Trifluoromethyl Groups

“…Particularly, most structural modifications of PAIs have been achieved by the development and subsequent polymerization of novel diimide-dicarboxylic acid monomers which can be easily prepared from diamine and commercially available trimellitic anhydride via simple refluxing in glacial acetic acid [ 20 , 21 ]. In contrast, imide- or amide-containing diamines have not been developed extensively, presumably because of relative synthetic inconvenience [ 22 ].…”