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通过草氨酸的氧化脱羧合成聚氨酯：通往自发泡泡沫的新途径。

Synthesis of polyurethanes through the oxidative decarboxylation of oxamic acids: a new gateway toward self-blown foams.

作者信息

Jaussaud Quentin, Ogbu Ikechukwu Martin, Pawar Govind Goroba, Grau Etienne, Robert Frédéric, Vidil Thomas, Landais Yannick, Cramail Henri

机构信息

University of Bordeaux, CNRS, Bordeaux INP, LCPO, UMR 5629 16 Avenue Pey-Berland F-33600 Pessac France

University of Bordeaux, CNRS, Bordeaux INP, ISM, UMR 5255 351, Cours de la Libération F-33400 Talence France

出版信息

Chem Sci. 2024 Jul 25;15(33):13475-13485. doi: 10.1039/d4sc02562h. eCollection 2024 Aug 22.

DOI:10.1039/d4sc02562h
PMID:39183929
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11339942/
Abstract

Polyurethane (PU) thermoplastics and thermosets were prepared through the step-growth polymerization of generated polyisocyanates through the decarboxylation of polyoxamic acids, in the presence of phenyliodine diacetate (PIDA), and polyols. The CO produced during the reaction allowed the access to self-blown polyurethane foams through an endogenous chemical blowing. The acetic acid released from ligand exchange at the iodine center was also shown to accelerate the polymerization reaction, avoiding the recourse to an additional catalyst. Changing simple parameters during the production process allowed us to access flexible PU foams with a wide range of properties.

摘要

通过在二醋酸碘苯（PIDA）存在下，使聚草氨酸脱羧生成的多异氰酸酯与多元醇进行逐步增长聚合反应，制备了聚氨酯（PU）热塑性塑料和热固性塑料。反应过程中产生的一氧化碳通过内源性化学发泡作用，使我们能够制得自发泡聚氨酯泡沫。碘中心配体交换释放出的乙酸也被证明可加速聚合反应，无需额外添加催化剂。在生产过程中改变简单参数，使我们能够获得具有广泛性能的柔性PU泡沫。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7da7/11339942/582f92ff41c3/d4sc02562h-f8.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7da7/11339942/bbdeff3945e4/d4sc02562h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7da7/11339942/ad72651ec945/d4sc02562h-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7da7/11339942/f75cda8b4366/d4sc02562h-f6.jpg
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本文引用的文献

1
PIDA-mediated Oxidative Decarboxylation of Oxamic Acids. The Role of Radical Acidity Enhancement.PIDA介导的草氨酸的氧化脱羧反应。自由基酸度增强的作用。
Chemistry. 2023 Mar 13;29(15):e202202963. doi: 10.1002/chem.202202963. Epub 2023 Feb 24.
2
Water-Induced Self-Blown Non-Isocyanate Polyurethane Foams.水致自发泡非异氰酸酯聚氨酯泡沫
Angew Chem Int Ed Engl. 2022 Dec 19;61(51):e202213422. doi: 10.1002/anie.202213422. Epub 2022 Nov 17.
3
Photocatalyzed decarboxylation of oxamic acids under near-infrared conditions.近红外条件下草氨酸的光催化脱羧反应
Chem Commun (Camb). 2022 Aug 4;58(63):8802-8805. doi: 10.1039/d2cc03155h.
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Oxamic acids: useful precursors of carbamoyl radicals.羟氨羧酸：有用的氨甲酰基自由基前体。
Chem Commun (Camb). 2022 Jul 7;58(55):7593-7607. doi: 10.1039/d2cc01953a.
5
Divergent Aminolysis Approach for Constructing Recyclable Self-Blown Nonisocyanate Polyurethane Foams.用于构建可回收自发泡非异氰酸酯聚氨酯泡沫的发散氨解方法
ACS Macro Lett. 2022 Feb 15;11(2):236-242. doi: 10.1021/acsmacrolett.1c00793. Epub 2022 Jan 20.
6
Cascade (Dithio)carbonate Ring Opening Reactions for Self-Blowing Polyhydroxythiourethane Foams.用于自发泡聚羟基硫脲泡沫的级联（二硫代）碳酸酯开环反应
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Blocking and Deblocking of Diisocyanate to Synthesize Polyurethanes.二异氰酸酯的封端与解封以合成聚氨酯
Polymers (Basel). 2021 Aug 27;13(17):2875. doi: 10.3390/polym13172875.
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From the Synthesis of Biobased Cyclic Carbonate to Polyhydroxyurethanes: A Promising Route towards Renewable Non-Isocyanate Polyurethanes.从生物基环状碳酸酯合成聚羟基聚氨酯：通往可再生非异氰酸酯聚氨酯的一条有前景的途径。
ChemSusChem. 2019 Aug 8;12(15):3410-3430. doi: 10.1002/cssc.201900737. Epub 2019 Jun 26.
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Chem Commun (Camb). 2018 Aug 16;54(67):9337-9340. doi: 10.1039/c8cc05462b.