Synthesis of degradable and chemically recyclable polymers using 4,4-disubstituted five-membered cyclic ketene hemiacetal ester (CKHE) monomers,Chemical Science

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Synthesis of degradable and chemically recyclable polymers using 4,4-disubstituted five-membered cyclic ketene hemiacetal ester (CKHE) monomers
Chemical Science ( IF 7.6 ) Pub Date : 2021-09-28 , DOI: 10.1039/d1sc03560f
Xin Yi Oh ₁ , Yicen Ge ₁ , Atsushi Goto ₁

Affiliation

Novel degradable and chemically recyclable polymers were synthesized using five-membered cyclic ketene hemiacetal ester (CKHE) monomers. The studied monomers were 4,4-dimethyl-2-methylene-1,3-dioxolan-5-one (DMDL) and 5-methyl-2-methylene-5-phenyl-1,3-dioxolan-4-one (PhDL). The two monomers were synthesized in high yields (80–90%), which is an attractive feature. DMDL afforded its homopolymer with a relatively high molecular weight (M_n >100 000, where M_n is the number-average molecular weight). DMDL and PhDL were copolymerized with various families of vinyl monomers, i.e., methacrylates, acrylates, styrene, acrylonitrile, vinyl pyrrolidinone, and acrylamide, and various functional methacrylates and acrylate. Such a wide scope of the accessible polymers is highly useful for material design. The obtained homopolymers and random copolymers of DMDL degraded in basic conditions (in the presence of a hydroxide or an amine) at relatively mild temperatures (room temperature to 65 °C). The degradation of the DMDL homopolymer generated 2-hydroxyisobutyric acid (HIBA). The generated HIBA was recovered and used as an ingredient to re-synthesize DMDL monomer, and this monomer was further used to re-synthesize the DMDL polymer, demonstrating the chemical recycling of the DMDL polymer. Such degradability and chemical recyclability of the DMDL polymer may contribute to the circular materials economy.

中文翻译：

使用4,4-二取代五元环烯酮半缩醛酯（CKHE）单体合成可降解且可化学回收的聚合物

使用五元环烯酮半缩醛酯（CKHE）单体合成了新型可降解且可化学回收的聚合物。研究的单体是 4,4-二甲基-2-亚甲基-1,3-二氧戊环-5-酮 (DMDL) 和 5-甲基-2-亚甲基-5-苯基-1,3-二氧戊环-4-酮 (PhDL) ）。这两种单体的合成产率很高（80-90%），这是一个有吸引力的特点。 DMDL 使其均聚物具有相对较高的分子量（ M _n >100 000，其中M _n是数均分子量）。 DMDL和PDL与各种乙烯基单体，即甲基丙烯酸酯、丙烯酸酯、苯乙烯、丙烯腈、乙烯基吡咯烷酮和丙烯酰胺，以及各种官能化的甲基丙烯酸酯和丙烯酸酯共聚。如此广泛的可获取聚合物对于材料设计非常有用。所得DMDL均聚物和无规共聚物在碱性条件（氢氧化物或胺存在）和相对温和的温度（室温至65℃）下降解。 DMDL 均聚物的降解产生 2-羟基异丁酸 (HIBA)。回收产生的HIBA并用作重新合成DMDL单体的成分，并且该单体进一步用于重新合成DMDL聚合物，证明了DMDL聚合物的化学回收利用。 DMDL聚合物的这种可降解性和化学可回收性可能有助于循环材料经济。

更新日期：2021-09-28

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