Polymers from ortho aromatic tetraamines and aromatic dianhydrides

Abstract

Aromatic heteropolymers were synthesized from aromatic tetraamines and dianhydrides; some of the polymers had a ladder‐type structure. The properties and thermal stability of the polymer were studied. The experimental conditions yielding the imidazolone structure were determined on model compounds. Polymers containing mixed aromatic units in the chain were prepared from pyromellitic anhydride or 3,3′,4,4′‐benzophenone tetracarboxylic dianhydride, and 3,3′‐diaminobenzidine, 3,3′,4,4′‐tetraaminodiphenyl ether, 1,4,5,8‐tetraaminonaphthalene, or 1,2,4,5‐tetraaminobenzene. The polycondensations were carried out in melt and in solution (in melted phenol, pyridine, dimethylacetamide, 116% polyphosphoric acid). The inherent viscosities of a number of polymers synthesized by melt condensation were in the range of approximately 0.2–0.7; the higher polymers were obtained by carrying out the polycondensations in solution in 116% polyphosphoric acid; in this case, the intrinsic viscosities ranged from 1.1 to 1.8. Most of the polymers do not melt at 350°C. and are soluble in the usual organic solvents, but the ladder‐type structure polymers were soluble only in concentrated sulfuric acid.

Nanostructured Conjugated Ladder Polymers for Stable and Fast Lithium Storage Anodes with High‐Capacity

“…In agreement with previous reports, the FT-IR spectra of BBL and SBBL show two broad bands around 1690 and 1560 cm −1 , which are associated with C=N and C=O vibrational modes in the aromatic rings ( Figure S1, Supporting Information). [29][30][31] XRD patterns of BBL show good crystallinity, which have two peaks at 11.7° and 26.3° ( Figure S2, Supporting Information). The results agree well with what have been reported by Xia and co-workers.…”

“…[ 29,30 ] 50 g PPA was added to a 100 mL twonecked fl ask fi tted with a stirrer and argon inlet and outlet. The PPA was deoxygenated by heating overnight at 110 °C with argon bubbling through the stirred acid.…”

“…BBL and SBBL were synthesized through one-pot polycondensation between 1,2,4,5-tetraaminobenzene tetrahydrobromide (TAB·4HBr) and NTCDA/PMDA in polyphosphoric acid (PPA), according to a literature method ( Figure 1 ). [ 29,30 ] The ladder polymers, BBL and SBBL are insoluble in most of solution excluding strong protonic acids, such as methanesulfonic acid (MSA), chlorosulfonic acid, and concentrated sulfuric acid, due to the protonation of the polymer chain. The solubility of BBL in MSA is better than other common strong protonic acids and it is also safer than others.…”

Synthesis and properties of PMR type poly(benzimidazopyrrolone‐imide)s

“…[1][2][3][4][5][6] However, the poor processability caused by the rigidity of polymer backbone limits their practical application in advanced technology. Improvement in the processability of polypyrrolones was attempted by polycondensation of biphenyl or bridged biphenyl dianhydrides with corresponding aromatic tetraamines to yield semi-ladder structures, 3,[5][6][7][8] or by incorporation of imide or imidazole segment into polymer backbone to produce linear poly(benzimidazo-pyrrolone-imide)s. 3,9,10 The copolymer consisting of pyrrolone and imide segments resulted in, to some extent, improvements in solubility without sacrificing thermal and mechanical properties.…”

Synthesis and properties of novel poly(benzimidazopyrrolone amide)s containing pyridine moieties

“…[1][2][3][4][5][6][7] Therefore, some efforts to improve the processability and flexibility of polypyrrolones, including the polycondensation of biphenyl or bridged biphenyl dianhydrides with aromatic tetraamines to yield semiladder structures [4][5][6]8 and the incorporation of imide or imidazole segments into the polymer backbone to produce linear poly(benzimidazopyrrolone imide)s, 4,[9][10][11][12] have been made; these studies have found that copolymers consisting of pyrrolone and imide segments resulted in, to some extent, an improvement in the processability without the sacrifice of thermal and mechanical properties. However, the poor processability and flexibility of polypyrrolones is still an unanswered problem.…”