Variation of Aliphatic Diisocyanates in Bio-Based TPUs

Journal Article · Wed Oct 25 00:00:00 UTC 2023 · Macromolecules

DOI: https://doi.org/10.1021/acs.macromol.3c00776 · OSTI ID:2503941

Rajput, Bhausaheb S. ^[1]; Forman, Aaron ^[1]; Halloran, Matthew W.  ^[1]; Phung Hai, Thien An ^[1]; Scofield, Gordon B. ^[2]; Burkart, Michael D.  ^[1]

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1. University of California San Diego, La Jolla, CA (United States)
2. Algenesis Materials, San Diego, CA (United States)

The utilization of bio-based materials for polymer production poses a challenge to both the industrial and academic sectors due to the availability and production costs of the necessary raw materials. Diisocyanates necessary for polyurethane synthesis have posed a particular challenge, given the paucity of natural diamine precursors for traditional phosgenation. We recently developed a phosgene-free flow chemistry methodology that allows for the safe, efficient, and scalable preparation of diisocyanates from naturally produced diacids. This chemistry broadens the potential for the development of renewable diisocyanates for a broad variety of applications. Here, we expand upon this work by demonstrating the scaled production of a panel of bio-based linear, aliphatic diisocyanates, with chain lengths ranging from four to eight carbons in good yields of 57–81% and high purity (~97%). Furthermore, these are applied to the synthesis of thermoplastic polyurethanes (TPUs) containing up to a 100% renewable carbon content. TPUs formulated using shorter carbon-chained diisocyanates displayed a higher tensile strength compared to those formulated using longer chains. Ready access to diisocyanates of varying chain length affords the ability to tailor TPU properties through careful selection of the diisocyanate, polyol, and chain extender, offering hard and soft TPUs for multiple end-use applications.

• Research Organization: University of California San Diego, La Jolla, CA (United States)
• Sponsoring Organization: National Science Foundation (NSF); USDOE Office of Energy Efficiency and Renewable Energy (EERE), Office of Sustainable Transportation. Bioenergy Technologies Office (BETO)
• Grant/Contract Number: EE0008246; EE0009295
• OSTI ID: 2503941
• Journal Information: Macromolecules, Journal Name: Macromolecules Journal Issue: 21 Vol. 56; ISSN 0024-9297
• Publisher: American Chemical SocietyCopyright Statement
• Country of Publication: United States
• Language: English