Thiol–ene Click Chemistry Incorporates Hydroxyl Functionality on Polycyclooctene to Tune Properties

Chethalen, Roshni John; Fastow, Eli J.; Coughlin, E. Bryan; Winey, Karen I.

doi:10.1021/acsmacrolett.2c00670

Title: Thiol–ene Click Chemistry Incorporates Hydroxyl Functionality on Polycyclooctene to Tune Properties

Journal Article · Thu Jan 05 00:00:00 EST 2023 · ACS Macro Letters

DOI:https://doi.org/10.1021/acsmacrolett.2c00670· OSTI ID:1924538

Chethalen, Roshni John ^[1];

^[2];

^[1];

^[2]

Univ. of Massachusetts, Amherst, MA (United States)
Univ. of Pennsylvania, Philadelphia, PA (United States)

Polyolefins compose the majority of plastic waste, but conventional mechanical recycling degrades their properties, thereby reducing their value. We report the functionalization of a model for dehydrogenated polyethylene, polycyclooctene (PCOE), with thiol–ene click chemistry to install pendant hydroxyl ethyl thioethers. Functionalization of PCOE using mercaptoethanol via thiol–ene click chemistry yielded functionalization between 1.4 and 22.9% based on ethylene monomeric units. Reactions were well-controlled by varying the reagent stoichiometry and reaction time. Crystallinity and melting temperature decreased, and glass transition temperature increased with greater functionalization. Contact angle measurements reveal an increase in surface polarity with functionalization. Here, comparisons with poly(ethylene-co-vinyl alcohol) (EVOH) show comparable surface polarity at similar levels of alcohol functionalization. At 12% functionalization, the ultimate shear stress (USS) of functionalized PCOE in an adhesive configuration is 4.10 ± 0.48 MPa, comparable to EVOH. At >12% functionalization, the failure mode changed from adhesive to mixed adhesive–cohesive, and the USS decreased.

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Research Organization:: Univ. of Pennsylvania, Philadelphia, PA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0022238

OSTI ID:: 1924538

Journal Information:: ACS Macro Letters, Vol. 12, Issue 1; ISSN 2161-1653

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Title: Thiol–ene Click Chemistry Incorporates Hydroxyl Functionality on Polycyclooctene to Tune Properties

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