ひまし油由来分解性エステル結合を有するポリテトラメチレングリコールの合成とそれによるリサイクル可能なポリウレタン材料の開発
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概要
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Ricinoleic acid derived from castor oil was utilized for the preparation of ester linkages-containing poly(tetramethylene ether) [or poly(tetrahydrofuran)] glycol{HO-CH[(CH2)5CH3]CH2CH=CH(CH2)7-C(=O)O-[(CH2)4O]n-1-(CH2)4-OC(=O)-(CH2)7-CH=CH-CH-CH2CH[(CH2)5CH3]-OH; PTHF-RA-OH}. This polyol was reacted with two-fold amount of 4,4'-diphenylmethane diisocyanate followed by the chain-extension reaction with 1,4-butanediol to give a new polyurethane with degradable ester moieties. The obtained polyurethane (PTHF-RA-BD-PU) exhibited similar thermal and mechanical properties to those of the polyurethane (PTHF-BD-PU) prepared from poly(tetramethylene ether)[or poly(tetrahydrofuran)]glycol (PTHF-OH). The treatment of PTHF-RA-BD-PU with potassium hydroxide in tetrahydrofuran/ethanol (9/1 v/v) solvent in the presence of a small amount of water caused hydrolysis reaction of the recinolate ester linkages to give the mixture of PTHF-OH and the urethane oligomers capped with recinoleic acid moieties. The extraction of PTHF-OH with methylene chloride from the mixture resulted in the recovery of PTHF-OH in over 90% yield based on the poly(tetrahydrofuran) segments of PTHF-RA-BD-PU. Enzymatic degradation of PTHF-RA-BD-PU was carried out with lipase as a catalyst. Both of the heterogeneous reaction with film speciments in water using phosphate buffer solution (pH 7.4) at 37â and the homegeneous reaction in N,N-dimethylformamide at 45â caused the decrease in the molecular weight of PTHF-RA-BD-PU. This is probably due to the lipase-catalyzed hydrolysis of the recinolate ester groups of PTHF-RA-BD-PU.
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