A novel shape memory poly(ε-caprolactone) network via UV-triggered thiol-ene reaction

Yang, Pengfei; Zhu, Guangming; Xu, Shuogui; Zhang, Xiaoyan; Shen, Xuelin; Chen, Xiaoping; Gao, Ye; Nie, Jing

doi:10.1002/polb.24314

Cited by 19 publications

(19 citation statements)

References 61 publications

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“…With the addition of 0.5 mol% DPAB, the reaction can perform quickly under visible light irradiation. Yang et al [ 58 ] reported a rapid start/stop thiol–ene reaction by turning on‐off the UV source, which produced a series of biodegradable shape memory materials. It can be seen from Figure that the growth of polymer chains in the light‐on periods followed a linear relationship between the M n and reaction time, whereas no M n growth was observed during the dark periods.…”

Section: Resultsmentioning

confidence: 99%

Polythioethers with Controlled α,ω‐End Groups Prepared by Visible Light Induced Thiol–Ene Click Polymerization of Dithiol and Divinyl Ether with 4‐(N,N‐diphenylamino)benzaldehyde as Organocatalyst

Zhang

Chen

et al. 2020

Macro Chemistry & Physics

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This study reports a step‐growth click‐polymerization of 1,4‐benzenedimethane (BDMT) and diethylene glycol divinyl ether (DEGVE) with 4‐(N,N‐diphenylamino)‐benzaldehyde (DPAB) as a photoredox catalyst under irradiation of visible light. DPAB exhibits a strong UV–vis absorption at 350 nm and a strong fluorescence emission at 480 nm in anisole. There is a strong fluorescence quenching between BDMT and DPAB. The molecular weight of the polythiolether can be controlled by reaction time and monomer feed ratios. More importantly, α,ω‐dithiol and α,ω‐divinyl telechelic polythiolether oligomers are successfully synthesized by simply changing the molar ratios of BDMT to DEGVE. 1H NMR and MALDI‐TOF MS spectra demonstrate that the oligomers have high end group fidelity. In addition, strong fluorescence is observed when the α,ω‐dithiol terminated polythiolether adds with N‐(1‐pyrenyl) maleimide, indicating that the as‐prepared polythiolether bears reactive thiol end groups. Furthermore, high molecular weight polythiolether are prepared by chain extension with reactive polythiolether oligomers as macro‐monomers. For example, α,ω‐divinyl oligomer (Mn = 2000 g mol−1) could further react with α,ω‐dithiol oligomer (Mn = 2400 g mol−1) to form high molecular weight polythiolether (Mn = 6000 g mol−1).

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Section: Resultsmentioning

confidence: 99%

Polythioethers with Controlled α,ω‐End Groups Prepared by Visible Light Induced Thiol–Ene Click Polymerization of Dithiol and Divinyl Ether with 4‐(N,N‐diphenylamino)benzaldehyde as Organocatalyst

Zhang

Chen

et al. 2020

Macro Chemistry & Physics

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“…The initial length was recorded as ɛ o , the sample was heated in a 60 °C water bath at a constant temperature for 1 min, then stretched to 200% (the length obtained was recorded as ɛ m ), cooled to room temperature, with an isothermal time of 1 min, unloaded external forces (the length after removal of load was recorded as ɛ u ), then placed into 60 °C hot water to recover its original shape (the length was recorded as ɛ p ), the shape memory test of all samples was repeated for three times. The shape recovery ratio ( R r ) and the shape fixity ratio ( R f ) were calculated by the following equations

R_{r} = \frac{ɛ_{u} - ɛ_{P}}{ɛ_{u} - ɛ_{o}} \times 100 %

R_{f} = \frac{ɛ_{u} - ɛ_{o}}{ɛ_{m} - ɛ_{o}} \times 100 %

…”

Section: Methodsmentioning

confidence: 99%

Biodegradable magnetic‐sensitive shape memory poly(ɛ‐caprolactone)/Fe₃O₄ nanocomposites

Gao

Zhu

et al. 2017

J of Applied Polymer Sci

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A novel biodegradable magnetic-sensitive shape memory poly(E-caprolactone) nanocomposites, which were crosslinked with functionalized Fe 3 O 4 magnetic nanoparticles (MNPs), were synthesized via in situ polymerization method. Fe 3 O 4 MNPs pretreated with g-(methacryloyloxy) propyl trimethoxy silane (KH570) were used as crosslinking agents. Because of the crosslinking of functionalized Fe 3 O 4 MNPs with poly(E-caprolactone) prepolymer, the properties of the nanocomposites with different content of functionalized Fe 3 O 4 MNPs, especially the mechanical properties, were significantly improved. The nanocomposites also showed excellent shape memory properties in both 60 8C hot water and alternating magnetic field (f 5 60, 90 kHz, H 5 38.7, 59.8 kA m 21 ).In hot water bath, all the samples had shape recovery rate (R r ) higher than 98% and shape fixed rate (R f ) nearly 100%. In alternating magnetic field, the R r of composites was over 85% with the highest at 95.3%. In addition, the nanocomposites also have good biodegradability.

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“…Considerable research has been devoted to the development of novel BSMP formulations that have the potential for use in medicine. For recent examples we direct the reader to the following references . In the Becker lab, we have developed amino acid‐based poly(ester urea)s (PEUs) and explored their shape memory behavior .…”

Section: Future and Outlookmentioning

confidence: 99%

Biodegradable Shape Memory Polymers in Medicine

Peterson

Dobrynin

Becker

2017

Adv Healthcare Materials

157

155

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Shape memory materials have emerged as an important class of materials in medicine due to their ability to change shape in response to a specific stimulus, enabling the simplification of medical procedures, use of minimally invasive techniques, and access to new treatment modalities. Shape memory polymers, in particular, are well suited for such applications given their excellent shape memory performance, tunable materials properties, minimal toxicity, and potential for biodegradation and resorption. This review provides an overview of biodegradable shape memory polymers that have been used in medical applications. The majority of biodegradable shape memory polymers are based on thermally responsive polyesters or polymers that contain hydrolyzable ester linkages. These materials have been targeted for use in applications pertaining to embolization, drug delivery, stents, tissue engineering, and wound closure. The development of biodegradable shape memory polymers with unique properties or responsiveness to novel stimuli has the potential to facilitate the optimization and development of new medical applications.

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A novel shape memory poly(ε-caprolactone) network via UV-triggered thiol-ene reaction

Cited by 19 publications

References 61 publications

Polythioethers with Controlled α,ω‐End Groups Prepared by Visible Light Induced Thiol–Ene Click Polymerization of Dithiol and Divinyl Ether with 4‐(N,N‐diphenylamino)benzaldehyde as Organocatalyst

Polythioethers with Controlled α,ω‐End Groups Prepared by Visible Light Induced Thiol–Ene Click Polymerization of Dithiol and Divinyl Ether with 4‐(N,N‐diphenylamino)benzaldehyde as Organocatalyst

Biodegradable magnetic‐sensitive shape memory poly(ɛ‐caprolactone)/Fe₃O₄ nanocomposites

Biodegradable Shape Memory Polymers in Medicine

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A novel shape memory poly(ε-caprolactone) network via UV-triggered thiol-ene reaction

Cited by 19 publications

References 61 publications

Polythioethers with Controlled α,ω‐End Groups Prepared by Visible Light Induced Thiol–Ene Click Polymerization of Dithiol and Divinyl Ether with 4‐(N,N‐diphenylamino)benzaldehyde as Organocatalyst

Polythioethers with Controlled α,ω‐End Groups Prepared by Visible Light Induced Thiol–Ene Click Polymerization of Dithiol and Divinyl Ether with 4‐(N,N‐diphenylamino)benzaldehyde as Organocatalyst

Biodegradable magnetic‐sensitive shape memory poly(ɛ‐caprolactone)/Fe3O4 nanocomposites

Biodegradable Shape Memory Polymers in Medicine

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Biodegradable magnetic‐sensitive shape memory poly(ɛ‐caprolactone)/Fe₃O₄ nanocomposites