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首页> 外文期刊>Bulletin of the Chemical Society of Japan >Preparation of α,ω-Diods of Long Carbon Chains and Their Use in Polyurethane Synthesis
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Preparation of α,ω-Diods of Long Carbon Chains and Their Use in Polyurethane Synthesis

机译：长碳链α，ω-二价烯烃的制备及其在聚氨酯合成中的应用

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摘要

NaH promoted coupling reaction of HO(CH_2)_(12)O-TBDMS (1, TBDMS-SiMe_2(t-Bu)) and Br(CH_2)_(12)O-TBDMS (2) followed by deprotection of the organosilyl groups affords HO(CH_2)_(12)O(CH_2)_(12)OH (5). 1,12-Dodecanediol reacts with an excess amount of 2 in the presence of NaH to give TBDMS-O(CH_2)_(12)O(CH_2)_(12)O(CH_2)_(12)O-TBDMS (6) which is turned into HO(CH_2)_(12)O(CH_2)_(12)O(CH_2)_(12)OH (7) by removal of the protecting groups. Similar 1 : 2 condensation of hydroquinone with 2 and with Br(CH_2)_6O-TBDMS (3) leads to formation of the corresponding α,ω-diols, HO(CH_2)_(12)OC_6H_4O(CH_2)_(12)OH (9) and HO(CH_2)_6OC_6H_4O(CH_2)_6OH (11), respectively. The four new long α,ω-diols are isolated and characterized by means of IR and NMR spectroscopy as well as elemental analyses. Polyaddition reactions of 5, 7, 9, and 11 to 1,3-bis(isocyanatomethly) benzene and 1,1'-methylenebis [4-isocyanatobenzene] give the corresponding poly (urethane)s in high yields. The obtained polymers, which were characterized by IR and NMR spectroscopy, have molecular weights over 20000 as determined from gel permeation chromatography using polystyrene standards.
机译：NaH促进HO（CH_2）_（12）O-TBDMS（1，TBDMS-SiMe_2（t-Bu））和Br（CH_2）_（12）O-TBDMS（2）的偶联反应，然后使有机甲硅烷基脱保护得到HO（CH_2）_（12）O（CH_2）_（12）OH（5）。 1,12-十二烷二醇在NaH存在下与过量2反应生成TBDMS-O（CH_2）_（12）O（CH_2）_（12）O（CH_2）_（12）O-TBDMS（6 ），通过除去保护基将其变成HO（CH_2）_（12）O（CH_2）_（12）O（CH_2）_（12）OH（7）。对苯二酚与2和与Br（CH_2）_6O-TBDMS的类似的1：2缩合反应导致形成相应的α，ω-二醇HO（CH_2）_（12）OC_6H_4O（CH_2）_（12）OH （9）和HO（CH_2）_6OC_6H_4O（CH_2）_6OH（11）。分离出四种新的长α，ω-二醇，并通过IR和NMR光谱以及元素分析对其进行表征。 5、7、9和11与1,3-双（异氰酸根合甲基）苯和1,1'-亚甲基双[4-异氰酸根合苯]的加聚反应可以高收率得到相应的聚氨基甲酸酯。通过IR和NMR光谱表征的所得聚合物，其分子量超过20000，如使用聚苯乙烯标准物的凝胶渗透色谱法所测定的。

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