The previously ignored or unreported impact of regiosomerism within diglycidyl ether of bisphenol F (DGEBF) on its network properties is presented. Routes to the isomers of DGEBF were explored: high-performance liquid chromatography showed good separation of the three isomers [--DGEBF (ppDGEBF), --DGEBF (poDGEBF), and --DGEBF (ooDGEBF)] with small yields; column chromatography gave good separation of pp- + po- from oo-DGEBF but pp-/po- separation was not achieved. Synthesis was optimized to crude yields of 76% for pp-; 87% for po-, and 86% for oo-. Subsequently, crosslinked networks were prepared with -xylylenediamine. With increasing ortho content, degradation of chemical resistance and an inherent weakening of the network was observed, that is, glass transition temperature ( ), beta transition temperature ( ), density, crosslink density, and the desorption diffusion coefficient decreased, whereas sorption diffusion coefficient and ultimate solvent uptake increased. This clearly shows that a subtle chemical structure change can significantly impact network performance.
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| http://dx.doi.org/10.1021/acs.macromol.9b01441 | DOI Listing |
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