Harnessing Catalysis Selectivity and Isophorone Diisocyanate Asymmetry for Tailored Polyurethane Prepolymers and Networks

Arnould, Priscilla; Simon, Frédéric; Fouquay, Stéphane; Pardal, Francis; Michaud, Guillaume; Gajan, David; Raynaud, Jean; Monteil, Vincent

doi:10.1021/acs.macromol.1c02491

Cited by 5 publications

(6 citation statements)

References 31 publications

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“…Certain investigations have revealed that in specific systems, MTBD or DBU tends to outperform TBD in terms of effectively catalyzing the addition of alcohols to isocyanates. 203,204…”

Section: S C H E M E 5mentioning

confidence: 99%

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Triazabicyclodecene: A versatile catalyst for polymer synthesis

Kim,

Lee,

Lee

2023

Journal of Polymer Science

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This comprehensive review aims to provide an in‐depth analysis of the catalytic performance of 1,5,7‐triazabicyclo[4,4,0]dec‐5‐ene (TBD) in polymer synthesis. TBD, a well‐established organic superbase, possesses a distinctive bifunctional character that grants it exceptional capabilities, particularly in processes such as transesterification or transamidation. TBD has garnered considerable attention since its initial report by Hedrick and Waymouth in 2006, and it has played a pivotal role in diverse polymerization reactions. Its versatility spans various polymerization modes, including chain‐growth and step‐growth polymerization, post‐polymerization modification, and network thermoset formation. More recently, its utility has extended to the green chemical recycling of polymers. By providing an encompassing overview of TBD's historical journey, this review delves into its past accomplishments while shedding light on its present and future potential to organocatalysts in polymer science.

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“…Certain investigations have revealed that in specific systems, MTBD or DBU tends to outperform TBD in terms of effectively catalyzing the addition of alcohols to isocyanates. 203,204…”

Section: S C H E M E 5mentioning

confidence: 99%

“…Within the realm of organocatalysts, it is important to note that TBD is not universally the optimal choice. Certain investigations have revealed that in specific systems, MTBD or DBU tends to outperform TBD in terms of effectively catalyzing the addition of alcohols to isocyanates 203,204 …”

Section: Tbd‐mediated Step‐growth Polymerizationmentioning

confidence: 99%

Triazabicyclodecene: A versatile catalyst for polymer synthesis

Kim,

Lee,

Lee

2023

Journal of Polymer Science

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“…However, the isocyanate group on C 1 appears to be less hindered than that on C 8 , which could enhance its reactivity. Indeed, it has been shown that in most instances, the secondary isocyanate group in IPDI exhibits higher reactivity due to lower steric hindrance in the chair conformation when compared to the quaternary isocyanate group [40,41]. Nevertheless, some catalysts have proven to be effective for activating both isocyanates in a similar manner [41][42][43][44][45][46][47][48].…”

Section: Influence Of Catalyst Nature On the Reactivity Of Pmdimentioning

confidence: 99%

Paving the Way towards Sustainability of Polyurethanes: Synthesis and Properties of Terpene-Based Diisocyanate

Delavarde,

Lemouzy,

Lebrun

et al. 2023

Molecules

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Due to growing concerns about environmental issues and the decline of petroleum-based resources, the synthesis of new biobased compounds for the polymer industry has become a prominent and timely topic. P-menthane-1,8-diamine (PMDA) is a readily available compound synthesized from turpentine, a cheap mixture of natural compounds isolated from pine trees. PMDA has been extensively used for its biological activities, but it can also serve as a source of valuable monomers for the polymer industry. In this work, commercial PMDA (ca. 85% pure) was purified by salinization, crystallization, and alkali treatment and then converted into p-menthane-1,8-diisocyanate (PMDI) through a phosgene-free synthesis at room temperature. A thorough analytical study using NMR techniques (1H, 13C, 13C-1H HSQC, 13C-1H HMBC, and 1H-1H NOESY) enables the characterization of the cis-trans isomeric mixtures of both PMDA and PMDI. These structural studies allowed for a better understanding of the spatial configuration of both isomers. Then, the reactivity of PMDI with a primary alcohol (benzyl alcohol) was studied in the presence of nine different catalysts exhibiting different activation modes. Finally, the use of PMDI in the synthesis of polyurethanes was explored to demonstrate that PMDI can be employed as a new biobased alternative to petrochemical-based isocyanates such as isophorone diisocyanate (IPDI).

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“…5,6 Tin-based catalysts are another class of popular and effective catalysts for the synthesis of polyurethanes. [7][8][9] One commonly used example is dibutyltin dilaurate (DBTDL), 10 which is also used for the synthesis of polyesters 11,12 and many other elastomers, especially for coating applications. 13 However, tin-based compounds are also toxic (with toxicity threshold of 3 ppm (ref.…”

Section: Introductionmentioning

confidence: 99%