Preparation and characterization of fluorine‐containing aromatic condensation polymers, 3. Preparation and characterization of fluorine‐containing aromatic poly(ketone)s and copoly(ketone)s by direct polycondensation of 4,4′‐[1‐(trifluoromethyl)trifluoroethylidene]dibenzoic acid and/or 4,4′ ‐isopropylidenedibenzoic acid with diaryl compounds

Abstract

Four types of fluorine-containing aromatic poly(ketone)s, poly(ether/ketone), poly(ketone), poly(sulfide/ketone) and poly(sulfone/ketone), were synthesized from 4,4'-[ 1 -(trifluoromethyl)trifluoroethylidene]dibenzoic acid and diaryl compounds, diphenyl ether, diphenyl ketone, diphenyl sulfide and diphenyl sulfone, by direct polycondensation using phosphorus pentoxide/ methanesulfonic acid as both condensing agent and solvent. The expected chemical structures were confirmed by IR and 'H NMR spectroscopy and elemental analysis. Two series of fluorinecontaining copoly(ketone)s, copoly(ether/ketone) and copoly(sulfide/ketone), were also similarly prepared by using different proportions of the dicarboxylic acid and the corresponding analogous 4,4'-isopropylidenedibenzoic acid but without fluorine, and the effect of the introduction of the fluorine atom on the properties of these polymers was discussed with relation to the fluorine contents. Most of the poly(ketone)s with and without fluorine were essentially amorphous and soluble in a wide range of organic solvents including chloroform and tetrahydrofuran, and afforded transparent films by solution casting. The contact angles of the films to water increased significantly and monotonously with increasing fluorine content in the copoly(ketone)s. Thermal properties such as glass transition temperature and thermal stability were also successfully improved by the introduction of a fluorine atom, and both of them increased markedly and monotonically with the increase of the fluorine content.

Preparation and characterization of fluorine-containing aromatic condensation polymers. VI. Aromatic polybenzothiazoles from 4,4?-(hexafluoroisopropylidene)dibenzoic acid and tetrafluoroterephthalic acid and 2,5-diamino-1,4-benzenedithiol dihydrochloride

“…12 A series of our studies matic PBIs containing perfluoroisopropylidene on the synthesis, characterization, and evaluation units were successfully synthesized from 4,4 -of fluorine-containing aromatic condensation (hexafluoroisopropylidene)dibenzoic acid ( Ia) polymers has also revealed that perfluoroisoproand aromatic tetramine hydrochlorides via the dipylidene unit-containing polymers, such as polyrect polycondensation using PPMA or PPA. These carbonates, 13 polyformals, 14 polyketones, 15 polypolymers dissolved easily in protic strong acids azomethines, 16 and their copolymers, have some and polar aprotic solvents and also even in less unique properties such as good solubility in orpolar m-cresol and pyridine, while maintaining ganic solvents, toughness and flexibility at low their high thermal stability. temperature, water and oil repellency, lower reIn this study, with the hope of providing organicfractive index, and high thermal stability in addisoluble aromatic PBTs, the synthesis of fluorinetion to the prominent characteristics inherent in containing PBTs was tried.…”

Synthesis and characterization of aromatic poly(ether ketone)s containing cyclotriphosphazene units. II

“…6 The observed broad molecular weight distributions of polymers are also not uncommon for the synthesis of PEK using Friedel-Crafts acylation polymerization. 9 In a typical 1 H NMR spectrum of polymer VII in CDCl 3 , the peaks that appeared at 6.88 and 7.55-7.85 ppm were assigned to sixteen aromatic protons of 4-fluorophenoxy groups and eight aromatic protons ortho to carbonyl groups, respectively (Fig. 2).…”

Preparation and characterization of fluorine-containing aromatic condensation polymers. VII. Aromatic polyacetals and copolyacetals from 2,2-bis(4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropane and/or 2,2-bis(4-hydroxyphenyl)propane and 2-(trifluoromethyl)benzal chloride

“…1 A series of studies on the synthesis, characterization, and evaluation of fluorinecontaining aromatic condensation polymers has revealed that hexafluoroisopropylidene-groupcontaining polymers, such as polyketones, 2 polyazomethines, 3 polybenzimidazoles, 4 polybenzothiazole, 5 and/or their respective copolymers, have unique properties such as good sol-ubility in organic solvents, toughness and flexibility at low temperatures, water and oil repellency, high thermal stability, and flame resistance in addition to the prominent characteristics inherent in the corresponding polymers without fluorine. Thus, the incorporation of hexafluoroisopropylidene groups into existing aromatic condensation polymers can not only make them soluble or processable but also give them additional characteristics.…”