Thermally Stable Bio Based Polycarbonate Using Dispiro Bornane Diol Derived from Camphorquinone and Glycerol via a One-step Ketalization Reaction

Abstract

Bio-based aliphatic polycarbonates with two cyclic ketal moieties were designed, and the bio-based dispiro bornane diol monomer (1',7',7'-trimethyldispiro[[1,3]dioxolane-2,2'-bicyclo[2,2,1]heptane-3',2''-[1,3]dioxolane]-4,4''-diyl)dimethanol, camphorquinone diketal glycerol, abbreviated as CaG) was synthesized from camphorquinone and glycerol to improve thermal properties of polymers and replace bisphenol A which is used in the polymer industry.

The novel bio-based diol monomer containing complex cyclic molecular structure was analyzed by FT-IR, 1H, 13C, and 2D-COSY NMR techniques. GPC results display that CaG was successfully proceeded and conducted to the high molecular weights for homopoly CaG carbonates (Mw = 18,652) abbreviated as PCaGC and for bisphenol-A (BPA) copolycarbonates (Mw = 78,482) as PCaG20BPA80C. The high glass transition and thermal stability of PCaGC and copolyCaGxBPAyC were studied by TGA and DSC and shown sufficiently high values temperature (Tg value from 128 to 151 ℃ and Td value above 350℃) for practical applications.

Given the high thermal stability and sufficient reactivity, CaG is a promising synthesis starting compound or renewable building block for applicable polymers.