Preparation and properties of a fast‐cross‐linking α‐cyanoacryloyloxyethyloxypropyl‐functionalized polydimethylsiloxane
Abstract α‐cyanoacryloyloxyethyloxypropyl‐functionalized polysiloxanes were prepared using a condensation reaction between the adduct of anthracene/α‐cyanoacryloyl chloride and hydroxyethyloxypropyl‐modified polydimethylsiloxanes, followed by a retro‐Diels–Alder reaction to deprotect the anthracene....
| Main Authors: | , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Wiley-VCH
2022-12-01
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| Series: | Nano Select |
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| Online Access: | https://doi.org/10.1002/nano.202200151 |
| _version_ | 1811178405794676736 |
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| author | Qingyue Liu Hong Dong Shiping Guo Yipin Zhang Erlei Wang Zhirong Qu Daowei Chen Liangbing Huang Jianchao Hou Yunfeng Zheng Chuan Wu |
| author_facet | Qingyue Liu Hong Dong Shiping Guo Yipin Zhang Erlei Wang Zhirong Qu Daowei Chen Liangbing Huang Jianchao Hou Yunfeng Zheng Chuan Wu |
| author_sort | Qingyue Liu |
| collection | DOAJ |
| description | Abstract α‐cyanoacryloyloxyethyloxypropyl‐functionalized polysiloxanes were prepared using a condensation reaction between the adduct of anthracene/α‐cyanoacryloyl chloride and hydroxyethyloxypropyl‐modified polydimethylsiloxanes, followed by a retro‐Diels–Alder reaction to deprotect the anthracene. Structures of the obtained polymers and their intermediates were characterized using 1H NMR, 13C NMR, and FT‐IR spectroscopies. Under mild conditions such as at room temperature with a relative humidity of 60%, the α‐cyanoacryloyloxyethyloxypropyl‐functionalized polysiloxanes could be completely cured within 3 minutes. With a small amount of N,N‐dimethyl‐p‐toluidine as the initiator, the curing time could be further shortened to 3–5 seconds. Various factors affected on the cross‐linking density and the average molecular weight between two adjacent cross‐linking points were investigated. The results indicated that with the introduction of the α‐cyanoacryloyloxyethyloxypropyl group, α‐cyanoacryloyloxyethyloxypropyl‐functionalized PDMS exhibited much better thermal stabilities than that of pure poly(ethyl α‐cyanoacrylate). Besides, the introduction of an α‐cyanoacryloyloxyethyloxypropyl group in the PDMS molecule also eliminated the crystallization behavior and glass transition temperature of PDMS. The results of the water contact angle test showed the interfacial characteristics of the prepared material changed significantly relative to pure PDMS. With the increase in the content of the functional group, the water contact angle of the material showed an overall increasing trend. |
| first_indexed | 2024-04-11T06:17:44Z |
| format | Article |
| id | doaj.art-bae4a1da1f414d848d1dfd2e2526f7bf |
| institution | Directory Open Access Journal |
| issn | 2688-4011 |
| language | English |
| last_indexed | 2024-04-11T06:17:44Z |
| publishDate | 2022-12-01 |
| publisher | Wiley-VCH |
| record_format | Article |
| series | Nano Select |
| spelling | doaj.art-bae4a1da1f414d848d1dfd2e2526f7bf2022-12-22T04:40:59ZengWiley-VCHNano Select2688-40112022-12-013121557157310.1002/nano.202200151Preparation and properties of a fast‐cross‐linking α‐cyanoacryloyloxyethyloxypropyl‐functionalized polydimethylsiloxaneQingyue Liu0Hong Dong1Shiping Guo2Yipin Zhang3Erlei Wang4Zhirong Qu5Daowei Chen6Liangbing Huang7Jianchao Hou8Yunfeng Zheng9Chuan Wu10College of Material Chemistry and Chemical Engineering Key Laboratory of Organosilicon Chemistry and Material Technology Ministry of Education Key Laboratory of Organosilicon Material Technology Hangzhou Normal University Zhejiang Province Hangzhou Zhejiang People's Republic of ChinaCollege of Material Chemistry and Chemical Engineering Key Laboratory of Organosilicon Chemistry and Material Technology Ministry of Education Key Laboratory of Organosilicon Material Technology Hangzhou Normal University Zhejiang Province Hangzhou Zhejiang People's Republic of ChinaCollege of Material Chemistry and Chemical Engineering Key Laboratory of Organosilicon Chemistry and Material Technology Ministry of Education Key Laboratory of Organosilicon Material Technology Hangzhou Normal University Zhejiang Province Hangzhou Zhejiang People's Republic of ChinaCollege of Material Chemistry and Chemical Engineering Key Laboratory of Organosilicon Chemistry and Material Technology Ministry of Education Key Laboratory of Organosilicon Material Technology Hangzhou Normal University Zhejiang Province Hangzhou Zhejiang People's Republic of ChinaCollege of Material Chemistry and Chemical Engineering Key Laboratory of Organosilicon Chemistry and Material Technology Ministry of Education Key Laboratory of Organosilicon Material Technology Hangzhou Normal University Zhejiang Province Hangzhou Zhejiang People's Republic of ChinaCollege of Material Chemistry and Chemical Engineering Key Laboratory of Organosilicon Chemistry and Material Technology Ministry of Education Key Laboratory of Organosilicon Material Technology Hangzhou Normal University Zhejiang Province Hangzhou Zhejiang People's Republic of ChinaNovel Silicone Research Institute Affiliated to Kaihua Synthetic Material Co. Ltd Zhejiang Wynca Chemical Industry Group Co. Ltd Kaihua Zhejiang People's Republic of ChinaNovel Silicone Research Institute Affiliated to Kaihua Synthetic Material Co. Ltd Zhejiang Wynca Chemical Industry Group Co. Ltd Kaihua Zhejiang People's Republic of ChinaNovel Silicone Research Institute Affiliated to Kaihua Synthetic Material Co. Ltd Zhejiang Wynca Chemical Industry Group Co. Ltd Kaihua Zhejiang People's Republic of ChinaNovel Silicone Research Institute Affiliated to Kaihua Synthetic Material Co. Ltd Zhejiang Wynca Chemical Industry Group Co. Ltd Kaihua Zhejiang People's Republic of ChinaCollege of Material Chemistry and Chemical Engineering Key Laboratory of Organosilicon Chemistry and Material Technology Ministry of Education Key Laboratory of Organosilicon Material Technology Hangzhou Normal University Zhejiang Province Hangzhou Zhejiang People's Republic of ChinaAbstract α‐cyanoacryloyloxyethyloxypropyl‐functionalized polysiloxanes were prepared using a condensation reaction between the adduct of anthracene/α‐cyanoacryloyl chloride and hydroxyethyloxypropyl‐modified polydimethylsiloxanes, followed by a retro‐Diels–Alder reaction to deprotect the anthracene. Structures of the obtained polymers and their intermediates were characterized using 1H NMR, 13C NMR, and FT‐IR spectroscopies. Under mild conditions such as at room temperature with a relative humidity of 60%, the α‐cyanoacryloyloxyethyloxypropyl‐functionalized polysiloxanes could be completely cured within 3 minutes. With a small amount of N,N‐dimethyl‐p‐toluidine as the initiator, the curing time could be further shortened to 3–5 seconds. Various factors affected on the cross‐linking density and the average molecular weight between two adjacent cross‐linking points were investigated. The results indicated that with the introduction of the α‐cyanoacryloyloxyethyloxypropyl group, α‐cyanoacryloyloxyethyloxypropyl‐functionalized PDMS exhibited much better thermal stabilities than that of pure poly(ethyl α‐cyanoacrylate). Besides, the introduction of an α‐cyanoacryloyloxyethyloxypropyl group in the PDMS molecule also eliminated the crystallization behavior and glass transition temperature of PDMS. The results of the water contact angle test showed the interfacial characteristics of the prepared material changed significantly relative to pure PDMS. With the increase in the content of the functional group, the water contact angle of the material showed an overall increasing trend.https://doi.org/10.1002/nano.202200151hydrogen‐containing polydimethylsiloxanehydrosilylation reactionretro‐Diels–Alder reactionα‐cyanoacryloyl chlorideα‐cyanoacryloyloxyethyloxypropyl‐functionalized polydimethylsiloxane |
| spellingShingle | Qingyue Liu Hong Dong Shiping Guo Yipin Zhang Erlei Wang Zhirong Qu Daowei Chen Liangbing Huang Jianchao Hou Yunfeng Zheng Chuan Wu Preparation and properties of a fast‐cross‐linking α‐cyanoacryloyloxyethyloxypropyl‐functionalized polydimethylsiloxane Nano Select hydrogen‐containing polydimethylsiloxane hydrosilylation reaction retro‐Diels–Alder reaction α‐cyanoacryloyl chloride α‐cyanoacryloyloxyethyloxypropyl‐functionalized polydimethylsiloxane |
| title | Preparation and properties of a fast‐cross‐linking α‐cyanoacryloyloxyethyloxypropyl‐functionalized polydimethylsiloxane |
| title_full | Preparation and properties of a fast‐cross‐linking α‐cyanoacryloyloxyethyloxypropyl‐functionalized polydimethylsiloxane |
| title_fullStr | Preparation and properties of a fast‐cross‐linking α‐cyanoacryloyloxyethyloxypropyl‐functionalized polydimethylsiloxane |
| title_full_unstemmed | Preparation and properties of a fast‐cross‐linking α‐cyanoacryloyloxyethyloxypropyl‐functionalized polydimethylsiloxane |
| title_short | Preparation and properties of a fast‐cross‐linking α‐cyanoacryloyloxyethyloxypropyl‐functionalized polydimethylsiloxane |
| title_sort | preparation and properties of a fast cross linking α cyanoacryloyloxyethyloxypropyl functionalized polydimethylsiloxane |
| topic | hydrogen‐containing polydimethylsiloxane hydrosilylation reaction retro‐Diels–Alder reaction α‐cyanoacryloyl chloride α‐cyanoacryloyloxyethyloxypropyl‐functionalized polydimethylsiloxane |
| url | https://doi.org/10.1002/nano.202200151 |
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