Preparation of polymers from di-(4-carboxyphenoxymethyl)methylphosphine oxide

Abstract

We know that the introduction of phosphorus into polymer molecules is associated with definite improvements in the properties of the materials, particularly as regards better non-inflammability, improved adhesion, and fairly frequently, good heat resistance. Korshak [1] and coworkers synthesized a number of phosphorylated polymers of di-(4-carboxyphenyl)-phenyl(methyl)phosphine oxide. The resulting products had better heat resistance in addition to self-extinguishing properties. These phosphine oxides are relatively difficult to obtain as their synthesis involves the use of Grignard reagents. It was recently shown [2] that di-(chloromethyl)methylphosphine oxide is relatively easy to prepare from tetra-(chloromethyl)phosphonium chloride. After this new phosphine oxides were synthesized by replacing the chlorine atoms in this compound by other groups: some of these new phosphine oxides also contained functional groups. For instance, di-(4-carbomethoxyphenoxymethyl)-methylphosphine oxide (OCMP) was prepared from di(chloromethyl)methylphosphine oxide and the methyl ester of 4-hydroxybenzoic acid.