Bio-based light-healing isocyanate-free polyurethanes derived from carbonated soybean oil and coumarin
ABSTRACTIn response to environmental concerns and restrictions on isocyanate-based materials, researchers and the coatings industry are focused on developing eco-friendly isocyanate-free polyurethanes. This article introduces a novel class of environmentally-friendly, initiator/catalyst-free, UV-cur...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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Taylor & Francis Group
2023-01-01
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| Series: | Green Chemistry Letters and Reviews |
| Subjects: | |
| Online Access: | https://www.tandfonline.com/doi/10.1080/17518253.2023.2283439 |
| _version_ | 1797450062921465856 |
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| author | Karteek Boga Nikhil Rambharosh Dhore Aruna Palanisamy Antonio F. Patti John C. Warner George P. Simon Kei Saito |
| author_facet | Karteek Boga Nikhil Rambharosh Dhore Aruna Palanisamy Antonio F. Patti John C. Warner George P. Simon Kei Saito |
| author_sort | Karteek Boga |
| collection | DOAJ |
| description | ABSTRACTIn response to environmental concerns and restrictions on isocyanate-based materials, researchers and the coatings industry are focused on developing eco-friendly isocyanate-free polyurethanes. This article introduces a novel class of environmentally-friendly, initiator/catalyst-free, UV-curable, self-healing non-isocyanate polyurethanes (NIPUs) synthesized from bio-based carbonated soybean oil (CSO) and non-toxic coumarin. The synthesis of these polymers is based on using a photo-reactive coumarin that undergoes a reversible [2 + 2] cycloaddition upon exposure to the wavelength of UV light. UV-curable three coumarin-terminated isocyanate-free polyurethane prepolymers were synthesized using CSO and three different amines and epoxy coumarin. Subsequently, a set of cross-linked NIPU polymers were obtained with exposure of 365 nm UV irradiation. The photo-reversible nature of these polymers was investigated in response to various wavelengths of UV radiation. Additionally, their self-healing ability and the thermal and mechanical properties of NIPU coatings were studied using optical microscopy, thermogravimetric analysis, differential scanning calorimetry, and a universal testing machine. The outcomes demonstrate that this polyurethane has the potential to provide a sustainable alternative to isocyanate-based materials. Two examples of stimulated healing are given, that of healing a scratch and the other being the healing of a sample that has been mechanically stressed to failure in a tensile mode. |
| first_indexed | 2024-03-09T14:35:06Z |
| format | Article |
| id | doaj.art-dd5d0b64c41044dba0c3db0925a5168c |
| institution | Directory Open Access Journal |
| issn | 1751-8253 1751-7192 |
| language | English |
| last_indexed | 2024-03-09T14:35:06Z |
| publishDate | 2023-01-01 |
| publisher | Taylor & Francis Group |
| record_format | Article |
| series | Green Chemistry Letters and Reviews |
| spelling | doaj.art-dd5d0b64c41044dba0c3db0925a5168c2023-11-27T14:52:10ZengTaylor & Francis GroupGreen Chemistry Letters and Reviews1751-82531751-71922023-01-0116110.1080/17518253.2023.2283439Bio-based light-healing isocyanate-free polyurethanes derived from carbonated soybean oil and coumarinKarteek Boga0Nikhil Rambharosh Dhore1Aruna Palanisamy2Antonio F. Patti3John C. Warner4George P. Simon5Kei Saito6School of Chemistry, Monash University Clayton, Clayton, AustraliaPolymers & Functional Materials Department, CSIR-Indian Institute of Chemical Technology, Hyderabad, IndiaPolymers & Functional Materials Department, CSIR-Indian Institute of Chemical Technology, Hyderabad, IndiaSchool of Chemistry, Monash University Clayton, Clayton, AustraliaSchool of Chemistry, Monash University Clayton, Clayton, AustraliaDepartment of Materials Science and Engineering, Monash University Clayton, Clayton, AustraliaGraduate School of Advanced Integrated Studies in Human Survivability, Kyoto University, Higashi-Ichijo-Kan, Kyoto, JapanABSTRACTIn response to environmental concerns and restrictions on isocyanate-based materials, researchers and the coatings industry are focused on developing eco-friendly isocyanate-free polyurethanes. This article introduces a novel class of environmentally-friendly, initiator/catalyst-free, UV-curable, self-healing non-isocyanate polyurethanes (NIPUs) synthesized from bio-based carbonated soybean oil (CSO) and non-toxic coumarin. The synthesis of these polymers is based on using a photo-reactive coumarin that undergoes a reversible [2 + 2] cycloaddition upon exposure to the wavelength of UV light. UV-curable three coumarin-terminated isocyanate-free polyurethane prepolymers were synthesized using CSO and three different amines and epoxy coumarin. Subsequently, a set of cross-linked NIPU polymers were obtained with exposure of 365 nm UV irradiation. The photo-reversible nature of these polymers was investigated in response to various wavelengths of UV radiation. Additionally, their self-healing ability and the thermal and mechanical properties of NIPU coatings were studied using optical microscopy, thermogravimetric analysis, differential scanning calorimetry, and a universal testing machine. The outcomes demonstrate that this polyurethane has the potential to provide a sustainable alternative to isocyanate-based materials. Two examples of stimulated healing are given, that of healing a scratch and the other being the healing of a sample that has been mechanically stressed to failure in a tensile mode.https://www.tandfonline.com/doi/10.1080/17518253.2023.2283439Polyurethanesoybean oilcoumarin[2 + 2] cycloadditionself-healinggreen chemistry |
| spellingShingle | Karteek Boga Nikhil Rambharosh Dhore Aruna Palanisamy Antonio F. Patti John C. Warner George P. Simon Kei Saito Bio-based light-healing isocyanate-free polyurethanes derived from carbonated soybean oil and coumarin Green Chemistry Letters and Reviews Polyurethane soybean oil coumarin [2 + 2] cycloaddition self-healing green chemistry |
| title | Bio-based light-healing isocyanate-free polyurethanes derived from carbonated soybean oil and coumarin |
| title_full | Bio-based light-healing isocyanate-free polyurethanes derived from carbonated soybean oil and coumarin |
| title_fullStr | Bio-based light-healing isocyanate-free polyurethanes derived from carbonated soybean oil and coumarin |
| title_full_unstemmed | Bio-based light-healing isocyanate-free polyurethanes derived from carbonated soybean oil and coumarin |
| title_short | Bio-based light-healing isocyanate-free polyurethanes derived from carbonated soybean oil and coumarin |
| title_sort | bio based light healing isocyanate free polyurethanes derived from carbonated soybean oil and coumarin |
| topic | Polyurethane soybean oil coumarin [2 + 2] cycloaddition self-healing green chemistry |
| url | https://www.tandfonline.com/doi/10.1080/17518253.2023.2283439 |
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