Novel Polyanhydrides with Enhanced Thermal and Solubility Properties

Abstract

A series of polyanhydrides based on o-, m-, and p-xylenes as derived from o-and p-hydroxybenzoic acids were synthesized by melt-condensation polymerization. Precursors, monomers, and polymers were characterized by NMR and IR spectroscopies, elemental and thermogravimetric analyses, and thermal transition temperatures. Polymers containing p-xylenes and p-hydroxybenzoic acids were relatively insoluble with high Tg's. In contrast, polymers containing o-and m-xylyl moieties based on o-hydroxybenzoic acids exhibit good solubilities and Tg's below 100°C.

In vitro degradation of an aromatic polyanhydride with enhanced thermal properties

“…The melting temperature (T m ) previously reported[9] was found to be due to impurities, as the poly( o CPX) used in this study did not exhibit a T m The originally reported T m = 114 °C for poly( o CPX) is near the o CPX methyl ester precursor T m = 120-122 °C.…”

“…The polymer was synthesized by methods previously reported (summarized in Figure 1 below),[9] resulting in a polymer with a weight average molecular weight = 5600 Da, a polydispersity = 2.1, and a T g = 68 °C. The melting temperature (T m ) previously reported[9] was found to be due to impurities, as the poly( o CPX) used in this study did not exhibit a T m The originally reported T m = 114 °C for poly( o CPX) is near the o CPX methyl ester precursor T m = 120-122 °C.…”

“…[9] This polymer is being evaluated as a biomaterial, specifically as a drug delivery matrix, because it is soluble in organic solvents and the T g value falls within a practical range for thermal processibility (∼68°C), while still being above physiological temperatures. [9] It is these solubility and thermal characteristics that permit the facile fabrication of microspheres, fibers, or films, and useful in biomedical applications.…”

Synthesis and characterization of antiseptic-based poly(anhydride-esters)

“…Molecular weight values for these poly(anhydride-esters) are typical for aromatic polyanhydrides synthesized by melt condensation. [26][27][28] The glass transition temperature (T g ) for these polymers ranged from 23 °C to 84 °C, with no indication of a melting temperature (T m ). Molecular weight and thermal properties are summarized in Table 1.…”

Engineering bioerodible polymers with tailored micro/nanostructure for vaccine delivery

“…Campo et al (1999) reported the solubility of Po-CPP and Po-CPH in THF to be 124 mg/ml and 130 mg/ml respectively. Anastasiou and Uhrich (2000a) and 400 °C (Yoda, 1963).…”