Synthesis of clickable hydrogels and linear polymers by type <scp>II</scp> photoinitiation

Murtezi, Eljesa; Çiftçi, Mustafa; Yaǧcı, Yusuf

doi:10.1002/pi.4786

Cited by 24 publications

(23 citation statements)

References 56 publications

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“…Initiating radicals are generated by electron and proton transfer through a charge transfer intermediate complex between CQ* and hydrogen donors such as tertiary amines. The polymerization reaction is initiated by the reactive amine radicals while the ketyl radicals dimerize . Alternatively, polymerization photoinitiated by CQ in the absence of co‐initiator has been reported in methacrylate monomers containing hydrogen donor groups such as methylene ether (OCH 2 ) .…”

Section: Resultsmentioning

confidence: 99%

Novel hydrogels based on a high‐molar‐mass water‐soluble dimethacrylate monomer

Asmussen

Gómez

Vallo

2018

Polymer International

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This report describes the preparation and swelling behaviour of novel hydrogels based on a water‐soluble dimethacrylate monomer (EBisEMA), which is characterized by a relatively high molar mass (Mn ∼ 1700 g mol−1) and contains a high proportion of aliphatic ether bonds in its structure. This feature results in moderately crosslinked and flexible polymer networks. Significant differences were observed in degree of swelling, depending on the synthesis method employed to obtain the hydrogels. The equilibrium water sorption of EBisEMA photopolymerized in bulk was 68 wt% while that of EBisEMA photopolymerized in aqueous solution (0.5 g mL−1) was 104 wt%. Thiol–methacrylate hydrogels were prepared by visible light photopolymerization of EBisEMA with a tetrafunctional thiol (PETMP) at various EBisEMA‐to‐PETMP molar ratios. These hydrogels contained unreacted thiol groups because of a faster homopolymerization reaction of EBisEMA. Hydrogels were also prepared in bulk by propylamine‐catalysed Michael addition reaction. No significant differences in swelling were observed between EBisEMA homopolymer and photocured EBisEMA–PETMP copolymer. Conversely, a marked increase in water uptake (110 wt%) was observed in the EBisEMA–PETMP hydrogels prepared by the Michael addition reaction catalysed by propylamine. These trends are explained in terms of a balance between the mass fraction of hydrophilic groups and the crosslinking density of the network. EBisEMA–PETMP hydrogels formulated with thiol in excess showed a noticeable tendency to adhere to diverse substrates, including paper, metals, glass and skin. This feature makes them especially attractive in applications for which adhesion is particularly critical such as dermatological patches. © 2018 Society of Chemical Industry

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Section: Resultsmentioning

confidence: 99%

Novel hydrogels based on a high‐molar‐mass water‐soluble dimethacrylate monomer

Asmussen

Gómez

Vallo

2018

Polymer International

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“…Diels‐Alder and copper‐catalyzed azide‐alkyne cycloaddition reactions (CuAAC) are the most common examples of segment coupling approach . We also showed CuAAC click reactions for the synthesis of various macromolecules such as block and graft copolymers.…”

Section: Introductionmentioning

confidence: 99%

A versatile approach for the preparation of end‐functional polymers and block copolymers by stable radical exchange reactions

Göksu

Yılmaz

Yaǧcı

2019

J. Polym. Sci. Part A: Polym. Chem.

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A versatile strategy for the preparation of end‐functional polymers and block copolymers by radical exchange reactions is described. For this purpose, first polystyrene with 2,2,6,6‐tetramethylpiperidine‐1‐oxyl end group (PS‐TEMPO) is prepared by nitroxide‐mediated radical polymerization (NMRP). In the subsequent step, these polymers are heated to 130 °C in the presence of independently prepared TEMPO derivatives bearing hydroxyl, azide and carboxylic acid functionalities, and polymers such as poly(ethylene glycol) (TEMPO‐PEG) and poly(ε‐caprolactone) (TEMPO‐PCL). Due to the simultaneous radical generation and reversible termination of the polymer radical, TEMPO moiety on polystyrene is replaced to form the corresponding end‐functional polymers and block copolymers. The intermediates and final polymers are characterized by 1H NMR, UV, IR, and GPC measurements. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 2387–2395

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“…For example, the dithioester and three dithioester groups of the polymerization product are unstable in high temperature and alkaline conditions, which restricts the practical application of the polymer . Recently, copper(I)‐ catalyzed azide − alkyne cycloaddition (CuAAC), commonly known as click chemistry, has become a very interesting tool for synthesizing biocompatible polymer‐based materials such as hydrogels or microgels due to its high efficiency, high tolerance of functional groups and solvents, and moderate reaction temperature . Whittaker's group utilized the CuAAC reaction to form networks from azide‐ N ‐isopropylacrylamide (azide‐NIPAM) and alkyne‐polyethylene glycol (alkyne‐PEG) chains that resulted in highly crosslinked hydrogels …”

Section: Introductionmentioning

confidence: 99%

Temperature and pH responsive hydrogels based on polyethylene glycol analogues and poly(methacrylic acid) via click chemistry

Sheng

Liu

et al. 2015

Polymer International

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A novel temperature responsive copolymer, poly[2-(2-methoxyethoxy)ethyl methacrylate-co-oligo(ethylene glycol) methacrylate-co-N-hydroxymethyl acrylamide] [P(MEO 2 MA-co-OEGMA-co-HMAM)], was synthesized by atom transfer radical polymerization. pH responsive poly(methacrylic acid) (PMAA) was synthesized by reversible addition-fragmentation chain transfer polymerization. After the hydroxyl groups on P(MEO 2 MA-co-OEGMA-co-HMAM) were transformed into azide groups and the carboxyl groups on PMAA were transformed into alkyne groups respectively, a novel temperature and pH responsive hydrogel was fabricated by click chemistry between the azide-P(MEO 2 MA-co-OEGMA-co-HMAM) and alkyne-PMAA in the presence of CuSO 4 and sodium ascorbate in aqueous solution. The rheological kinetics of gel formation demonstrated that gelation had commenced within 5 min at 25 ∘ C, since then the storage modulus (G ′ ) was higher than the loss modulus (G ′′ ). SEM images of hydrogel morphology and the swelling ratios of hydrogel at different temperatures and pH proved that the formed hydrogel had temperature and pH sensitivities. Bovine serum albumin was used as a model to evaluate the sustained release of the hydrogel; the results indicated that the hydrogel was a promising candidate for controlling protein drug delivery.

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Synthesis of clickable hydrogels and linear polymers by type II photoinitiation

Cited by 24 publications

References 56 publications

Novel hydrogels based on a high‐molar‐mass water‐soluble dimethacrylate monomer

Novel hydrogels based on a high‐molar‐mass water‐soluble dimethacrylate monomer

A versatile approach for the preparation of end‐functional polymers and block copolymers by stable radical exchange reactions

Temperature and pH responsive hydrogels based on polyethylene glycol analogues and poly(methacrylic acid) via click chemistry

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