Interfacial polycondensation method used in the synthesis of polymers containing phosphorus in the main chain

Abstract

Polyphosphoesters gained importance especially due to their use as flame retardants and as biocompatible and biodegradable materials for medicine and in the pharmaceutical industry. This paper presents the results obtained by our research group in the synthesis of polyphosphoesters by interfacial polycondensation. This reaction is rapid and irreversible polymerization at the interface between a phase containing one difunctional intermediate and another phase containing a complementary difunctional reactant. Different methods like liquid–liquid, vapor–liquid or solid<uni-2013;liquid were used in the synthesis of polyphosphates of polyphosphonates using aliphatic/aromatic phosphoric/phosphonic dichlorides and different diols. Aqueous NaOH, or tripotasium phosphate were used as bases. In almost all cases a catalyst is not needed.

Synthesis, thermal analysis, and linear and nonlinear optical characterization of substituted polyphosphonates derived from 1,12-dodecanediol

“…Polyphosphonates (Chart ) are a highly modular class of hybrid inorganic/organic polymers. The properties of these polymers are highly tunable via the appropriate choice of the X, R, and R′ groups, therefore making them accessible for a variety of applications . In addition, this class of polymers possesses thermal stabilities similar to those of organic systems such as poly(methyl methacrylate), polystyrene, polyethylene, or polypropylene…”

Semicrystalline Long-Chain Polyphosphoesters from Polyesterification

“…The phosphorus hydroxide species (P–OH) nominally formed along with alkyl chloride further reacts with a phosphorus chloride species to the P–O–P anhydride group, which occurs to a small extent in the polymer backbone . This results in the formation of three different stereoisomers: the meso-anhydride as well as the two racemic anhydrides.…”

“…The phosphorus hydroxide species (P−OH) nominally formed along with alkyl chloride further reacts with a phosphorus chloride species to the P−O−P anhydride group, which occurs to a small extent in the polymer backbone. 35 This results in the formation of three different stereoisomers: the meso-anhydride as well as the two racemic anhydrides. These species are observable at δ = 22.6 and δ = 22.3 ppm for PPEXMe 36,37 and at δ = −19.1 ppm and δ = −19.3 ppm for PPEX(OPh) 38 by 31 P{ 1 H} NMR spectroscopy (Figure 2).…”

Vapor phase interfacial polymerization: a method to synthesize thin film composite membranes without using organic solvents

“…[17][18][19] More specifically, polyphosphoesters were obtained by interfacial polycondensation in a vapor-liquid system in which an organic solvent was not required. 20 However, none of these approaches pretended to produce the polyamide membranes studied here. In any event, this research is in line with others carried out to reduce the harmful effect of organic solvents and monomers during TFC membrane preparation.…”