Synthesis and characterization of new poly(aryl ether ketone)s bearing (4-phenoxyphenyl)triphenylmethane moieties

Abstract

1,1-Bis(4-hydroxyphenyl)-1-(4-phenoxyphenyl)-1-phenylmethane (BHPPPPM), a new bisphenol monomer, was synthesized with 65% yield from 4-benzoyl diphenyl ether in a one-pot, two-step synthetic procedure. Four new poly(aryl ether ketone)s (PAEKs) bearing (4-phenoxyphenyl)triphenylmethane moieties were prepared from BHPPPPM with four difluorinated aromatic ketones via a nucleophilic substitution reaction. The polycondensation proceeded in tetramethylene sulfone in the presence of anhydrous potassium carbonate and afforded the new PAEKs in nearly quantitative yields with inherent viscosities of 0.60-0.78 dL g À1 . The resulting PAEKs having number-average molecular weights in the range of 29,500-34,200 g mol À1 with the polydispersity index ranged from 1.94 to 2.01 are all amorphous and show high glass transition temperatures ranging from 174 C to 196 C, excellent thermal stability, and the temperatures at the 5% weight loss are over 500 C with char yields above 60% at 700 C under nitrogen atmosphere. These new PAEKs are all soluble in polar aprotic solvents such as N-methyl-2-pyrrolidone and N,N 0 -dimethylacetamide and could also be dissolved in chloroform and tetrahydrofuran. All the polymers formed transparent, strong, and flexible films with tensile strengths of 78-85 MPa, tensile moduli of 1.9-2.4 GPa, and elongations at break of 7-10%.

Synthesis and characterization of new aromatic polyesters with a (4-phenoxyphenyl)phenylmethene linkage

“…BHPPPPM 24 (1) and 2-(4-trifluoromethylphenoxy) terephthaloyl chloride 25 (2f) were prepared according to our reported procedures. Terephthaloyl chloride (2a, TPC), isophthaloyl chloride (2b, IPC) and aromatic dicarboxylic acids such as 4,4 0 -oxy bisbenzoic acid, 4,4 0 -dicarboxybiphenyl and 2,2-bis(4-carboxyphenyl)hexafluoropropane were obtained from Xiya Reagent Co. Ltd (China).…”

“…Recently, we have synthesized poly(ether ketone)s containing (4-phenoxyphenyl)triphenylmethane moieties in the polymer backbone from 1,1-bis(4-hydroxyphenyl)-1-(4-phenoxyphenyl)-1-phenylmethane (BHPPPPM). 24 These polymers exhibited better thermal resistance and solubility in polar aprotic and chlorinated solvents. In this study, a series of new aromatic polyesters containing a (4-phenoxyphenyl)phenylmethene linkage were prepared based on the reaction between BHPPPPM with aromatic diacid chlorides such as terephthaloyl chloride (TPC), isophthaloyl chloride (IPC), 4,4 0 -biphenyldicarbonyl chloride, 4,4 0 -oxydibenzoyl chloride, 2,2-bis(chloroformylphenyl)-1,1,1,3,3,3hexafluoropropane, and 2-(4-trifluoromethylphenoxy)terephthaloyl chloride by interfacial polycondensation.…”

Next generation high‐performance carbon fiber thermoplastic composites based on polyaryletherketones

“…(a) PEKK copolymer containing imide linkage to improve thermal resistance and mechanical properties at elevated temperature . (b) Pendant groups to improve solubility for film casting from solution . (c) Pendant groups to enhance the dielectric constant and hydrophobicity …”

“…Other PAEKs were synthesized with (4‐phenoxyphenyl)triphenylmethane moieties in the main chain [Figure (b)] . The polymers have good solubility in organic solvents at room temperature and were successfully cast into films from solutions.…”

Synthesis and characterization of soluble copoly(arylene ether ketone sulfone)s bearing xanthene moiety in the main chain

“…To overcome these limitations, various structural modification of the polymer backbone has been tried toward the improvement of solubility and processability of PEKs. These approaches include the alteration of the order and ratio of ether–ketone linkages 4 as well as the ratio of meta and para phenyl unit, 5 the insertion of flexible thioether 6 and CR 2 7 groups, the introduction of pendent groups such as methyl, 8 trifluoromethyl, 9 t -butyl, 10 phenyl, 11 trifluorophenyl, 12,13 pyridyl, 14 naphthyl, 15 and bulky cardo groups such as fluorene, 16 acenaphthenequinone, 17 spirodilactam, 18 phthalide, 19 and decahydronaphthalene, 20 as well as the incorporation of unsymmetrical or noncoplanar structure. 21 –24 Among them, the introduction of sulfone groups into the PEK chain to give poly(arylene ether ketone sulfone) (PEKS) could be another important way to induce significant variations of properties.…”