對苯二酚衍生異質雙官能基高分子中間體之合成及應用

廖宜哲

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對苯二酚衍生異質雙官能基高分子中間體之合成及應用

Synthesis of Hydroquinone Derived Dual Functional Polymer Intermediates and Applications

廖宜哲 , Masters　　Advisor：戴憲弘　　

繁體中文

對苯二酚異質雙官能基中間體；交替式合成；精準聚胺酯硬鏈段；窄分子量分佈；熱交聯中間體；交聯高分子； hydroquinone-dual functional polymer intermediate ； iterative synthesis ； precise length PU hard-segment ； narrow molecular weight distribution ； heat-curable intermediate ； crosslinkable polymers

Abstract │ Reference (46) │ Times Cited (2) │ Altmetrics

Abstract 〈TOP〉

Parallel Abstract 〈TOP〉

This research used an inexpensive commodity chemical, bisphenol A (BPA), as the starting material to synthesize several dual functional intermediates of hydroquinone (HQ) in four consecutive steps. In the first step, BPA was cracked into isopropenyl phenol (IPP) and separated from phenol. This is followed by the first functionalization reactions of IPP at its phenolic hydroxyl group to give isopropenyl phenyl ethers. Then, the intermediates were oxidized at isopropenyl group with hydrogen peroxide to give mono-functionalized HQ derivatives. In the final step, newly generated phenolic groups were again converted into the final products by the second functionalization. Efficient high yield synthesis were achieved in each step in this straightforward strategy with overall yields of >56% for the entire four steps.
　　The usefulness of dual functional intermediate was exemplified by synthesis of linear urethane monol and diol, it through iterative syntheses based on reactivity difference of two hydroxyl groups. In all these step-wise syntheses, high selectivity, high purity and low dispersity have been achieved. In order to demonstrate utility of diol, it was used as a hard-segment extender in the preparation of polyurethane elastomers, PU1. PU1 was found to have substantial superior performances in Td and mechanical properties over the PU2 which was prepared with the same basic components in the PU formulation but without pre-making of the ordered extender. The formation of distinctive phase-segregations in PU1 due to aggregate of the ordered hard segments is believed to be the major cause of the differences.
　　In another application of dual functional HQ was subjected to react with polyisocyanates or polyacid chlorides at its ethoxylated alcohol site in making multiple functional propargyl poly-intermediates with either urethane or ester linkages. The yields of these four intermediates are all well over 90%. These compounds were then spread as a thin films on glasses and thermally cured. Since the curing reaction of propargyl groups occurred only at a temperature of over 200 oC, only ester were found to cured to form cross-linked polymers with enhanced thermal and mechanical properties. Particularly, the hardness increased 184.3 sec. in a hardness test.
　　Through this reseach, the four-step synthetic methodology developed can make many different dual functional intermediates for testings in precision syntheses and applications in the future.

Reference ( 46 ) 〈TOP〉

2.Washio, I.; Shibasaki, Y.; Ueda, M. Macromolecules 2005, 38, 2237.
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6.陳星儒. 國立中興大學化學工程學系碩士論文, 2009.
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7.郭明杰. 國立中興大學化學工程學系博士論文, 2009.
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8.蘇哲民. 國立中興大學化學工程學系碩士論文, 2009.
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19.Crivello, J. V.; Lai, Y. L. J. Polym. Sci., Part A: Polym. Chem. 1995, 33, 653.
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