Chonghui Wang

Blends of polyester having amino sulfonic acid moieties with poly(vinyl alcohol) and their metal complex formation

Polyester having amino sulfonic acid moieties (TBES) was prepared by a liquid/solid biphase polycondensation of terephthaloyl chloride (TPC) and N,N-bis(2-hydroxyethyl)-2-aminoethanesulfonic acid (BES) in trimethyl phosphate (TMP) using triethylamine (TEA) as an acid acceptor. Blends of TBES with PVA and their metal complexes with Ni2+ and Co2+ ions were prepared. A strong interaction was observed between TBES and PVA. An electric conductivity of 10−6 S cm−1 was attained for the blend films containing about 5 wt % water. A coordination structure with two chelate rings is proposed for the metal complex with Ni2+ and Co2+ ions when the molar ratio of amino sulfonic acid groups in TBES to metal ions is larger than 2. Polymer blends complexed with Ni2+ or Co2+ ions result in semi-interpenetrating polymer networks from chelate formation.

Chemoselective polycondensation of isophthaloyl chloride with multifunctional monomers containing hydroxyl groups and sulfamino acid or amino acid moiety

It is shown that the nucleophilicity of hydroxyl groups and sulfonic acid or carboxyl group in multifunctional monomer (N,N-bis[2-hydroxyethyl]-2-aminoethanesulfonic acid (BES) and N,N-di[2-hydroxyethyl]glycine (DHG)) and their reactivity to isophtaloyl chloride (IPC) depends strongly on their solubility in trimethyl phosphate (TMP). When these multifunctional monomers react heterogeneously in TMP, both hydroxyl groups and the sulfonic acid or carboxyl group react with IPC, resulting in crosslinked polymers. When the reaction occurs homogeneously in TMP, IPC reacts exclusively with hydroxyl groups of BES and DHG leaving sulfonic acid and carboxyl groups unreacted, yielding zwitterionic polyesters

Synthesis of reactive aromatic polyesters having pendant chlorohydrin moieties

A monomer containing a chlorohydrin moiety, propyl chlorohydrin diphenolate (PCHDP), was synthesized. Reactive polyesters having these pendant chlorohydrin moieties were prepared by the interfacial polycondensation of isophthaloyl chloride with PCHDP or with PCHDP and diphenolic acid using phase transfer catalyst. The molar ratio of reactants and the phase ratio of water to organic solvent strongly affect the molecular weight of resulting polymers and polymers with high molecular weight are obtained at the molar ratio of 1.0–1.15 and the phase ratio of 2.0–3.5. Swelling of the growing polymers is dependent on the molar ratio of the reactants and the phase ratio because of the hydrophilic and hydrophobic nature of the pendant chlorhydrin moiety. The resulting polymers are not soluble in any solvent except water in which hydrolysis occurs. Thus so, the structure of polymers was confirmed by 13C CP/MAS NMR.

Synthesis of polyphosphate and polyphosphate ester having pendant amine salt groups

Abstract Seven cyclic and noncyclic organic phosphates have been examined for the reactivity to polycondensation. Polyphosphate and polyphosphate ester having pendant tertiary amine salt groups are obtained from a cyclic organic phosphate having a primary amine salt group and a tertiary amine salt group by a molten organic phosphate phase/organic phase polycondensation method. A novel concept of the zwitterion polycondensation mechanism is proposed. The chemical structure of the resulting polymers was confirmed from infrared spectra, solid state 31 P and 13 C NMR spectra.

Synthesis of copolyesters having tertiary amine groups or zwitterion moieties in the main chain

Copolyesters having tertiary amine groups or zwitterion moieties in the main chain were prepared from terephthaloyl chloride (TPC) and mixtures of bisphenol A and aliphatic diols such as N-ethyldiethanolamine (EDA), N,N-bis(2-hydroxyethyl)-2-aminoethanesulfonic acid (BES) and N,N-bis(2-hydroxyethyl)glycine (BHG) by a liquid/solid biphase polycondensation in trimethyl phosphate (TMP) as well as a water phase/organic phase interfacial polycondensation. The composition of copolymers obtained by the biphase polycondensation is close to that of the feeds. The nucleophilicity of hydroxyl groups of these aliphatic diols is increased in TMP and the solvent TMP participates in the reaction. In the water phase/organic phase interfacial polycondensation, the copolyester (P1) from EDA has a higher aliphatic diol residue content than P2 and P3 from BES and BHG, because the self-nucleophilic catalysis of the tertiary amine groups of the resulting polymer occurs in the organic phase. The copolyesters (P2 and P3) having pendant hydrophilic groups contain very few aliphatic diol residues because the self-nucleophilic catalysis of the tertiary amine groups takes place in the water phase and the extensive hydrolysis of the intermediate occurs, which results from TPC with the tertiary amine groups during the reaction.