Networks Based on Poly(α‐methylene‐δ‐valerolactone‐<i>co</i>‐δ‐valerolactone): Crosslinking Through Free‐Radical Vinyl Copolymerization

Stöhr, Olesja; Ritter, Helmut

doi:10.1002/macp.201300674

Cited by 13 publications

(10 citation statements)

References 19 publications

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“…a-Methylidene-d-valerolactone (A23) has usually been polymerized as ''vinyl monomer''. Ritter and coworkers 86 reported the first polymerization by ring-opening. Formylation of d-valerolactone, subsequent formyl transfer and elimination of a carboxylate anion yielded A23 (yield: 57%, Scheme 5).…”

Section: Polyestersmentioning

confidence: 99%

Functional biodegradable polymers via ring-opening polymerization of monomers without protective groups

2018

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Biodegradable polymers are of current interest and chemical functionality in such materials is often demanded in advanced biomedical applications. Functional groups often are not tolerated in the polymerization process of ring-opening polymerization (ROP) and therefore protective groups need to be applied. Advantageously, several orthogonally reactive functions are available, which do not demand protection during ROP. We give an insight into available, orthogonally reactive cyclic monomers and the corresponding functional synthetic and biodegradable polymers, obtained from ROP. Functionalities in the monomer are reviewed, which are tolerated by ROP without further protection and allow further post-modification of the corresponding chemically functional polymers after polymerization. Synthetic concepts to these monomers are summarized in detail, preferably using precursor molecules. Post-modification strategies for the reported functionalities are presented and selected applications highlighted.

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Section: Polyestersmentioning

confidence: 99%

Functional biodegradable polymers via ring-opening polymerization of monomers without protective groups

2018

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“…On the other hand, direct copolymerization of MBL and ε ‐CL by lanthanide‐based coordination polymerization catalysts in toluene at low temperature (below 0 °C) leads to the exclusive formation of the ring‐opening copolyester PMBL‐ co ‐PCL, with the MBL incorporation up to 40 mol % without any detectable vinyl‐addition homopolymer PMBL formation . Ring‐opening copolymerizations of exo ‐methylene‐lactones bearing six‐ and seven‐membered rings with their respective parent lactones (i.e., δ ‐valerolactone and ε ‐CL) proceed smoothly to form the corresponding unsaturated copolyesters …”

Section: Introductionmentioning

confidence: 99%

Polymerizability of Exo‐methylene‐lactide toward vinyl addition and ring opening

Miyake

Zhang

Chen

2015

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

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This work examines the stereochemical control and polymerizability of exo-methylene-lactide (MLA) or (6S)-3-methylene-6-methyl-1,4-dioxane-2,5-dione, a chiral monomer derived from L-lactide, toward vinyl-addition and ring-opening polymerization (ROP) pathways, respectively. Currently, no information on the stereochemistry of the vinyl-addition polymerization of MLA is known, and the possible ROP pathway is unexplored. Accordingly, this work first investigated the stereochemical control and other characteristics of the radical polymerization of MLA and its copolymerization with an analogous exo-methylene-lactone, c-methyl-a-methylene-c-butyrolactone (MMBL), and di-methylene-lactide (DMLA) or 3,6-dimethylene-1,4-dioxane-2,5-dione. The MLA homopolymerization produced optically active, but atactic, vinyl-type polymers having a specific rotation of [a]

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“…Scheme shows the reaction pathway of the hydroxyl‐functionalized lactones 4 . The first step was conducted according to the procedure in our previously reported work . The product 3 was reacted with 2‐mercaptoethanol in bulk under basic conditions (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Hyperbranched polyesters based on hydroxyalkyl-lactones via thiol-ene click reaction

Stöhr

Ritter

2014

Polym. Int.

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The preparation of AB 2 monomers via thiol-ene click reaction from six-and seven-membered unsaturated lactones is described. The hydroxyl-functionalized valerolactone was prepared by use of Michael thiol-ene-addition reaction starting from 2-mercaptoethanol and 3-methylenetetrahydro-2H-pyran-2-on. The hydroxyl-functionalized caprolactone was prepared radically from 2-mercaptoethanol and 7-allyloxepan-2-one. Both AB 2 monomers were polymerized via ring opening in the presence of tin(II)-2-ethylhexanoate (Sn(Oct) 2 ) as a catalyst yielding the hyperbranched polyesters. The new hyperbranched polyesters were analyzed by 13 C NMR spectra to determine the degree of branching.

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Networks Based on Poly(α‐methylene‐δ‐valerolactone‐co‐δ‐valerolactone): Crosslinking Through Free‐Radical Vinyl Copolymerization

Cited by 13 publications

References 19 publications

Functional biodegradable polymers via ring-opening polymerization of monomers without protective groups

Functional biodegradable polymers via ring-opening polymerization of monomers without protective groups

Polymerizability of Exo‐methylene‐lactide toward vinyl addition and ring opening

Hyperbranched polyesters based on hydroxyalkyl-lactones via thiol-ene click reaction

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