Fully Renewable Non‐Isocyanate Polyurethanes via the Lossen Rearrangement,Macromolecular Rapid Communications

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Fully Renewable Non‐Isocyanate Polyurethanes via the Lossen Rearrangement
Macromolecular Rapid Communications ( IF 4.2 ) Pub Date : 2020-09-16 , DOI: 10.1002/marc.202000440
Luca Filippi ₁ , Michael A R Meier _{1,

2}

Affiliation

In this work, a straightforward and efficient synthesis approach to renewable non‐isocyanate polyurethanes (NIPUs) is described. For this purpose, suitable and renewable carbamate monomers, possessing two double bonds, are synthesized from hydroxamic fatty acid derivatives via the Lossen rearrangement in a one‐step synthesis, and sustainable dithiols are synthesized from dialkenes derived from renewable feedstock (i.e., limonene and 1,4‐cyclohexadiene). Subsequently, the comonomers are polymerized with the highly efficient thiol–ene reaction to produce NIPUs with M_n values up to 26 kg mol⁻¹ bearing thioether linkages. The main side product of the Lossen rearrangement, a symmetric urea, can also be polymerized in the same fashion. Important in the view of sustainability, the monomer mixture can also be used directly, without separation. The obtained polymers are characterized by NMR, attenuated total reflection‐infrared spectroscopy, differential scanning calorimetry, and size exclusion chromatography.

中文翻译：

通过Lossen重排的完全可再生的非异氰酸酯聚氨酯

在这项工作中，描述了一种可再生的非异氰酸酯聚氨酯（NIPU）的简单有效的合成方法。为此，可以通过一步法合成由异羟肟酸脂肪酸衍生物通过Lossen重排合成具有两个双键的合适的可再生氨基甲酸酯单体，并从可再生原料（即li烯和1 ，4-环己二烯）。随后，将共聚单体与高效硫醇-烯反应以生产NIPUs聚合中号_Ñ值高达26公斤摩尔^-1带有硫醚键。Lossen重排的主要副产物对称尿素也可以相同的方式聚合。从可持续性的角度来看很重要，单体混合物也可以不分离而直接使用。获得的聚合物通过NMR，衰减全反射红外光谱，差示扫描量热法和尺寸排阻色谱进行表征。

更新日期：2020-09-16

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