Facile preparation of poly(N-isopropylacrylamide)-based hydrogels via aqueous Diels–Alder click reaction

Wei, Hongliang; Yang, Zhe; Chu, Huijuan; Zhu, Jing; Li, Zhicheng; Cui, Jin-Shi

doi:10.1016/j.polymer.2010.02.008

Cited by 59 publications

(48 citation statements)

References 42 publications

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“…As reported in our previous papers, 20,21 in order to suppress the gelation which may be attributed to lability of the carbon-5 of the furan ring during polymerization of furan derivatives, herein, the initial total concentration of the monomers was also reduced to 0.3 mol/L. The GPC data show that all the obtained macromers have a unimodal peak with a polydispersity index (PDI) less than 3 (Table I).…”

Section: Resultssupporting

confidence: 54%

“…This motivated us to investigate Diels-Alder reaction between diene-functionalized polymers and dienophile-functionalized polymers in water, and some interesting results have already been observed. [19][20][21] Therefore, DA reaction was used to prepare injectable hydrogels during the tandem physical and chemical cross-linking herein. On the other hand, thermosensitive poly(N-isopropylacrylamide) (PNIPA) exhibits a unique soluble-insoluble change at its lower critical solution temperature (LCST).…”

Section: Introductionmentioning

confidence: 99%

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Preparation of thermosensitive hydrogels by means of tandem physical and chemical crosslinking

et al. 2011

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The tandem physical and chemical crosslinking was used to prepare injectable hydrogels. First, the terpolymers with diene groups were synthesized by the free radical copolymerization of N-isopropylacrylamide (NIPA), N,N-dimethylacrylamide (DMA) and furfuryl methacrylate (FM). Second, dienophile-functionalized terpolymers were obtained from the terpolymers of NIPA, DMA, and 2-hydroxyethyl methacrylate (HEMA) and Nmaleoyl alanine (AMI) by a coupling reaction under N,N'-dicyclohexylcarbodiimide (DCC). When the screened diene-functionalized terpolymer and dienophile-functionalized terpolymer were dissolved separately in water and mixed, physically cross-linked hydrogels formed rapidly within 10 s at 37 o C. Subsequently, the physically crosslinked hydrogels could change gradually into chemically cross-linked hydrogels by a Diels-Alder reaction and the mechanical strength of the hydrogels could be improved. The swelling behavior study suggests that the hydrogels possess thermosensitivity and good reproducibility at different temperatures. The strategy described, i.e. incorporating the advantages of physically crosslinked hydrogels and chemically crosslinked hydrogels, has potential applications in the preparation of injectable hydrogels.

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Section: Resultssupporting

confidence: 54%

Section: Introductionmentioning

confidence: 99%

Preparation of thermosensitive hydrogels by means of tandem physical and chemical crosslinking

et al. 2011

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“…10 Furfuryl methacrylate was also copolymerized with different monomers and the DA reaction was carried out with bismaleimides based on different amino acids modified with maleic anhydride. [11][12][13] In this context, we previously designed DA hydrogels from poly(2-aminoethyl methacrylate)-based furan and maleimide counterparts.…”

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confidence: 99%

Hydrogel synthesis by aqueous Diels‐Alder reaction between furan modified methacrylate and polyetheramine‐based bismaleimides

García‐Astrain

Algar

Gandini

et al. 2014

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

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A simple method for preparing cross-linked hydrogels in an aqueous medium is investigated using Diels-Alder (DA) "click" reaction, without employing a catalyst. A polymeric diene is first synthesized by the functionalization of poly(2-aminoethyl methacrylate) hydrochloride with furfural. Suited bisdienophiles are prepared by modification of Jeffamine V R ED of different molecular weights with maleic anhydride. Both precursors of the DA coupling are thoroughly characterized before their reactions. The ensuing hydrogels are analyzed in terms of their microstructure, swelling, and rheological behavior, as a function of the reaction conditions. The influence of the molecular weight of the cross-linker and the furan-to-maleimide ratio on the final properties of the hydrogels were also investigated.

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“…The Diels-Alder reaction, highly selective [4 + 2] cycloaddition between a diene and a dienophile without a catalyst, is also known as a click type reaction. Diels-Alder click crosslinked PEG [38], NIPAAm [39], or hyaluronic acid (HA) [40,41] based hydrogels have been investigated for tissue engineering applications. 1 There has been an increased interest in the enzymatically crosslinked hydrogels that shows few side reactions since their high specificity for substrates.…”

Section: Chemical Hydrogelsmentioning

confidence: 99%

Introduction to In Situ Forming Hydrogels for Biomedical Applications

Choi

Loh

Tan

et al. 2014

In-Situ Gelling Polymers

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In situ gelling polymer aqueous solutions undergo sol-to-gel transition through chemical and/or physical crosslinking. The criterion on sol and gel is an important issue, therefore, rheology of hydrogel have been discussed in detail. The in situ gelling system has been investigated for minimally invasive drug delivery, injectable tissue engineering, gene delivery, and wound healing. In this chapter, in situ gelling systems and their various biomedical applications were briefly summarized.

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Facile preparation of poly(N-isopropylacrylamide)-based hydrogels via aqueous Diels–Alder click reaction

Cited by 59 publications

References 42 publications

Preparation of thermosensitive hydrogels by means of tandem physical and chemical crosslinking

Preparation of thermosensitive hydrogels by means of tandem physical and chemical crosslinking

Hydrogel synthesis by aqueous Diels‐Alder reaction between furan modified methacrylate and polyetheramine‐based bismaleimides

Introduction to In Situ Forming Hydrogels for Biomedical Applications

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