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The aza-Michael reaction: towards semi-crystalline polymers from renewable itaconic acid and diamines†
Polymer Chemistry ( IF 4.1 ) Pub Date : 2019-06-20 00:00:00 , DOI: 10.1039/c9py00463g G. J. Noordzij 1, 2, 3, 4, 5 , Y. J. G. van den Boomen 1, 2, 3, 4, 5 , C. Gilbert 1, 2, 3, 4, 5 , D. J. P. van Elk 1, 2, 3, 4, 5 , M. Roy 1, 2, 3, 4, 5 , C. H. R. M. Wilsens 1, 2, 3, 4, 5 , S. Rastogi 1, 2, 3, 4, 5
Polymer Chemistry ( IF 4.1 ) Pub Date : 2019-06-20 00:00:00 , DOI: 10.1039/c9py00463g G. J. Noordzij 1, 2, 3, 4, 5 , Y. J. G. van den Boomen 1, 2, 3, 4, 5 , C. Gilbert 1, 2, 3, 4, 5 , D. J. P. van Elk 1, 2, 3, 4, 5 , M. Roy 1, 2, 3, 4, 5 , C. H. R. M. Wilsens 1, 2, 3, 4, 5 , S. Rastogi 1, 2, 3, 4, 5
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This study reports, for the first time, semi-crystalline polymers based on bis-pyrrolidone dicarboxylic acids (BPDA) derived from renewable itaconic acid and various diamines. Rigid BPDA monomers could be obtained in high purity and yield from dimethyl itaconate, instead of the normally used itaconic acid as the starting material. The reduction in the melting point of dimethyl-BPDA monomers, compared to that of normal BPDA monomers, enables melt-polycondensation thus avoiding the need for a solvent in the oligomerization step. Under standard polycondensation conditions, the dimethyl-BPDA monomer with a rigid trans-cyclohexanediamine (t-CH-BPDA) could readily be polymerized with linear aliphatic diols (C6 to C12) to yield high molecular weight polyesters. These polyesters are the first in their class to be reported semi-crystalline, having a Tg between 65 and 33 °C and a Tm between 213 and 184 °C, with an increasing aliphatic chain length. Furthermore, even in the presence of hydrophilic pyrrolidone groups, semi-crystalline polyesters based on t-CH-BPDA showed high stability in water with no significant water uptake. Preliminary studies show that t-CH-BPDA monomers can also be polymerized into semi-crystalline polyamides, although insolubility and an unstable melt prevented the accurate characterization of the synthesized polyamides. Though trans-cyclohexanediamine is currently not available from biomass, the potential biomass content in the described semi-crystalline polyesters ranges from 71% for the C6 diol up to 81% for the C12 diol.
中文翻译：
氮杂-迈克尔反应：由可再生的衣康酸和二胺合成半结晶聚合物†
这项研究首次报道了基于双吡咯烷酮二羧酸（BPDA）的半结晶聚合物，该聚合物衍生自可再生的衣康酸和各种二胺。刚性的BPDA单体可以从衣康酸二甲酯获得高纯度和收率，而不是通常使用的衣康酸作为起始原料。与普通的BPDA单体相比，二甲基-BPDA单体的熔点降低使得能够进行熔融缩聚，从而避免了在低聚步骤中对溶剂的需求。在标准缩聚条件下，具有刚性反式-环己二胺（t -CH-BPDA）的二甲基-BPDA单体可以很容易地与线性脂肪族二醇（C 6至C 12）聚合）以产生高分子量聚酯。这些聚酯是同类中第一个被报道为半结晶的聚酯，其T g在65至33°C之间，T m在213至184°C之间，且脂族链长不断增加。此外，即使在存在亲水的吡咯烷酮基团的情况下，基于t -CH-BPDA的半结晶聚酯在水中也显示出高稳定性，而没有明显的吸水率。初步研究表明，尽管不溶性和不稳定的熔体阻碍了合成聚酰胺的准确表征，但t -CH-BPDA单体也可以聚合成半结晶聚酰胺。虽然反式-环己二胺目前无法从生物质中获得，所述半结晶聚酯中潜在的生物质含量范围从C 6二醇的71％到C 12二醇的81％不等。
更新日期：2019-06-20
中文翻译：
氮杂-迈克尔反应：由可再生的衣康酸和二胺合成半结晶聚合物†
这项研究首次报道了基于双吡咯烷酮二羧酸（BPDA）的半结晶聚合物，该聚合物衍生自可再生的衣康酸和各种二胺。刚性的BPDA单体可以从衣康酸二甲酯获得高纯度和收率，而不是通常使用的衣康酸作为起始原料。与普通的BPDA单体相比，二甲基-BPDA单体的熔点降低使得能够进行熔融缩聚，从而避免了在低聚步骤中对溶剂的需求。在标准缩聚条件下，具有刚性反式-环己二胺（t -CH-BPDA）的二甲基-BPDA单体可以很容易地与线性脂肪族二醇（C 6至C 12）聚合）以产生高分子量聚酯。这些聚酯是同类中第一个被报道为半结晶的聚酯，其T g在65至33°C之间，T m在213至184°C之间，且脂族链长不断增加。此外，即使在存在亲水的吡咯烷酮基团的情况下，基于t -CH-BPDA的半结晶聚酯在水中也显示出高稳定性，而没有明显的吸水率。初步研究表明，尽管不溶性和不稳定的熔体阻碍了合成聚酰胺的准确表征，但t -CH-BPDA单体也可以聚合成半结晶聚酰胺。虽然反式-环己二胺目前无法从生物质中获得，所述半结晶聚酯中潜在的生物质含量范围从C 6二醇的71％到C 12二醇的81％不等。
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