Bifunctional diazirine reagent for covalent dyeing of Kevlar and inert polymer materials
We report a convenient bifunctional diazirine reagent that is capable of photochemically modifying inert polymers, particularly those used in fibers and textiles for ballistics and blast protective gear, such as para-aramid and ultra-high molecular weight polyethylene (UHMWPE). The reagent's st...
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| Format: | Article |
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Royal Society of Chemistry
2024
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| Online Access: | https://hdl.handle.net/1721.1/154143 |
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| author | Liu, Richard Y. Luo, Shao-Xiong Lennon Hirst, Elizabeth S. Doona, Christopher J. Swager, Timothy M. |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Liu, Richard Y. Luo, Shao-Xiong Lennon Hirst, Elizabeth S. Doona, Christopher J. Swager, Timothy M. |
| author_sort | Liu, Richard Y. |
| collection | MIT |
| description | We report a convenient bifunctional diazirine reagent that is capable of photochemically modifying inert polymers, particularly those used in fibers and textiles for ballistics and blast protective gear, such as para-aramid and ultra-high molecular weight polyethylene (UHMWPE). The reagent's structure features a trifluoromethyl diazirine group as a precursor to a carbene that binds the textile surface. On the reagent's other terminus, a benzyl bromide group acts as a site accessible for substitution reactions. As a bench-stable liquid, this bifunctional diazirine can be prepared on gram-scale quantities and rapidly activates under long-wave UV light. A series of fabrics made from Kevlar, Spectra, Dyneema, etc. were functionalized with this diazirine reagent, then subsequently dyed by binding nucleophilic dyes. The resulting coloration was found to be robust and colorfast with respect to water, organic solvent, and simulated laundering with detergent, and the strength of the fibers or fabrics was retained through the dyeing process, as shown through TGA and mechanical break testing. Overall, this carbene-based method provides a general, mild strategy for the covalent attachment of small molecules to textiles made from inert polymers, particularly para-aramids and UHMWPE, as well as nylon and fiber blends of these materials, and has potential use in next-generation protective outerwear. |
| first_indexed | 2024-09-23T12:22:04Z |
| format | Article |
| id | mit-1721.1/154143 |
| institution | Massachusetts Institute of Technology |
| last_indexed | 2025-02-19T04:21:08Z |
| publishDate | 2024 |
| publisher | Royal Society of Chemistry |
| record_format | dspace |
| spelling | mit-1721.1/1541432025-01-08T04:48:57Z Bifunctional diazirine reagent for covalent dyeing of Kevlar and inert polymer materials Liu, Richard Y. Luo, Shao-Xiong Lennon Hirst, Elizabeth S. Doona, Christopher J. Swager, Timothy M. Massachusetts Institute of Technology. Department of Chemistry Organic Chemistry Polymers and Plastics Biochemistry Bioengineering We report a convenient bifunctional diazirine reagent that is capable of photochemically modifying inert polymers, particularly those used in fibers and textiles for ballistics and blast protective gear, such as para-aramid and ultra-high molecular weight polyethylene (UHMWPE). The reagent's structure features a trifluoromethyl diazirine group as a precursor to a carbene that binds the textile surface. On the reagent's other terminus, a benzyl bromide group acts as a site accessible for substitution reactions. As a bench-stable liquid, this bifunctional diazirine can be prepared on gram-scale quantities and rapidly activates under long-wave UV light. A series of fabrics made from Kevlar, Spectra, Dyneema, etc. were functionalized with this diazirine reagent, then subsequently dyed by binding nucleophilic dyes. The resulting coloration was found to be robust and colorfast with respect to water, organic solvent, and simulated laundering with detergent, and the strength of the fibers or fabrics was retained through the dyeing process, as shown through TGA and mechanical break testing. Overall, this carbene-based method provides a general, mild strategy for the covalent attachment of small molecules to textiles made from inert polymers, particularly para-aramids and UHMWPE, as well as nylon and fiber blends of these materials, and has potential use in next-generation protective outerwear. U.S. Army Combat Capabilities Development Command Soldier Center 2024-04-12T18:12:35Z 2024-04-12T18:12:35Z 2023 Article http://purl.org/eprint/type/JournalArticle 1759-9954 1759-9962 https://hdl.handle.net/1721.1/154143 Liu, Richard Y., Luo, Shao-Xiong Lennon, Hirst, Elizabeth S., Doona, Christopher J. and Swager, Timothy M. 2023. "Bifunctional diazirine reagent for covalent dyeing of Kevlar and inert polymer materials." Polymer Chemistry, 14 (36). PUBLISHER_CC 10.1039/d3py00907f Polymer Chemistry Creative Commons Attribution-Noncommercial https://creativecommons.org/licenses/by-nc/3.0/ application/pdf Royal Society of Chemistry Royal Society of Chemistry |
| spellingShingle | Organic Chemistry Polymers and Plastics Biochemistry Bioengineering Liu, Richard Y. Luo, Shao-Xiong Lennon Hirst, Elizabeth S. Doona, Christopher J. Swager, Timothy M. Bifunctional diazirine reagent for covalent dyeing of Kevlar and inert polymer materials |
| title | Bifunctional diazirine reagent for covalent dyeing of Kevlar and inert polymer materials |
| title_full | Bifunctional diazirine reagent for covalent dyeing of Kevlar and inert polymer materials |
| title_fullStr | Bifunctional diazirine reagent for covalent dyeing of Kevlar and inert polymer materials |
| title_full_unstemmed | Bifunctional diazirine reagent for covalent dyeing of Kevlar and inert polymer materials |
| title_short | Bifunctional diazirine reagent for covalent dyeing of Kevlar and inert polymer materials |
| title_sort | bifunctional diazirine reagent for covalent dyeing of kevlar and inert polymer materials |
| topic | Organic Chemistry Polymers and Plastics Biochemistry Bioengineering |
| url | https://hdl.handle.net/1721.1/154143 |
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