Nucleophile-initiated and thermal bulk polymerizations of cyclic trimethylene carbonate in the absence of added catalysts

Sépulchre, Maurice; Dourges, Marie-Anne; Neblai, Mirna

doi:10.1002/1521-3935(20000801)201:13<1405::aid-macp1405>3.0.co;2-t

Cited by 13 publications

(23 citation statements)

References 31 publications

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“…The network formation was proposed to result from intermolecular transesterification. This explanation is supported by reports of intermolecular transesterification in tin(II) 2‐ethylhexanoate‐catalyzed polymerization of polylactones, as well as for the catalyst‐free polymerization of linear TMC using alcohols as initiators . The extent of intermolecular transesterification is influenced by numerous factors, including polymerization temperature, monomer‐initiator ratio, polymerization time, and the nature of the initiator .…”

Section: Resultssupporting

confidence: 62%

Tough and Enzyme‐Degradable Hydrogels

Chen

Taghavi

Marecak

et al. 2017

Macro Materials & Eng

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Mechanically robust hydrogels that degrade only via cell action have potential as scaffolds for the generation of load‐bearing soft connective tissue. This study demonstrates that terminally acrylated 4‐arm‐poly(ethylene glycol)‐block‐oligo(trimethylene carbonate) (4a‐PEG‐(TMC)n) can be readily reacted with a collagenase‐degradable bis‐cysteine peptide to form hydrogels. The inclusion of the TMC blocks renders the hydrogels mechanically tough when tested under compression, with modulus and toughness values within the range of those of articular cartilage. Moreover, the hydrogels formed are resistant to degradation by hydrolysis in the absence of collagenase but degrade via surface erosion in the presence of collagenase. The strategy employed to form these hydrogels is readily tailored to create a variety of tough, enzyme‐degradable hydrogels of varying mechanical and degradation properties.

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Section: Resultssupporting

confidence: 62%

Tough and Enzyme‐Degradable Hydrogels

Chen

Taghavi

Marecak

et al. 2017

Macro Materials & Eng

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“…The spectrum of the as‐polymerized unpurified PTMC is collected in order to estimate the percentage of monomer conversion and average molecular weight of the polymer before purification. The spectrum in Figure 1A shows chemical shifts that are in perfect agreement with the dihydroxy‐terminated PTMC structure:47 partially overlapped signals in the range of δ = 4.4–4.0 ppm are attributed to protons of the methylene group adjacent to the carbonate group, which belong to chain terminal units (c) and to internal repeating units (d). In the range δ = 2.2–1.8 ppm, partially overlapped signals attributed to protons of the ‘central’ methylene group, which belong to terminal chain units (b) and to internal repeating units (e), are observed.…”

Section: Resultsmentioning

confidence: 61%

“…A well‐established procedure to synthesize PTMC is the ring‐opening polymerization (ROP) of cyclic TMC monomer, which can be conducted with different catalysts and initiators, such as organometallic compounds of tin37–39 and aluminium,40, 41 alcohols,42, 43 and enzymes,44–46 etc. In particular, Sepulchre et al investigated the synthesis of PTMC by bulk ROP using two different diols as nucleophilic initiators: propan‐1,3‐diol and 4‐(hydroxymethyl)benzyl alcohol) 47. When diols are employed the polymerization can proceed at both sides of the initiator molecule and the final product is a dihydroxy‐terminated polymer chain.…”

Section: Resultsmentioning

confidence: 99%

“…When diols are employed the polymerization can proceed at both sides of the initiator molecule and the final product is a dihydroxy‐terminated polymer chain. Moreover, the molecular weight of the synthesized polymer can be controlled by choosing the appropriate monomer‐to‐initiator molar ratio, thanks to the pseudo‐living character of the process 47…”

Section: Resultsmentioning

confidence: 99%

“…Besides the typical PTMC signals, the spectrum also shows a triplet in the range of δ = 4.5–4.4 ppm, attributed to the presence of unreacted TMC monomer units in the unpurified polymer. Indeed the TMC monomer should show47 signals at 4.5–4.4 ppm (f) and at 2.2–2.1 ppm (g). In the present case, signal (g) is not visible because it is hidden by the (b) and (e) signals of PTMC.…”

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

Organic–Inorganic Interactions in Poly(trimethylene carbonate)–Titania Hybrids

Cortecchia

Mazzocchetti

Scandola

2009

Macro Chemistry & Physics

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Polycarbonate–titania hybrids have been synthesized by a sol–gel reaction, starting from poly(trimethylene carbonate) (PTMC) and titanium isoproproxide in different ratios. PTMC with a given chain length was obtained by ring opening polymerization. FT‐IR spectra reveal the presence of TiOC covalent bonds between organic and inorganic phases, and their number increases with increasing inorganic phase content. Solvent extractions show that hybrid soluble fraction contains low $\overline M _{\rm n}$ PTMC chains with isopropoxide ends, which suggests that TiOC bond formation is mainly promoted by transesterification reactions of isopropyl alcohol onto the polymer chain, catalyzed by Ti compounds. Hybrid thermal properties reflect the combined effect of the decrease of PTMC molecular weight and of bond formation between PTMC and the inorganic network. The nanometric dimension of the TiO2 domains, confirmed by atomic force microscopy, provides optically transparent hybrids.magnified image

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Synthesis and characterization of poly‐α,β‐[N‐(2‐hydroxyethyl)‐L‐aspartamide]‐g‐poly(L‐lactide) biodegradable copolymers as drug carriers

Peng

Cheng

Zhuo

2005

J Biomedical Materials Res

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A series of biodegradable amphiphilic graft polymers were successfully synthesized by grafting poly(L-lactide) (PLLA) sequences onto a water-soluble polymer poly-alpha,beta-[N-(2-hydroxyethyl)-L-aspartamide] (PHEA) backbone. We established the feasibility of preparing these novel graft polymers by the ring-opening polymerization initiated by the macroinitiator PHEA bearing hydroxyl groups without adding any catalyst. The successful grafting of PLLA sequences onto the PHEA backbone was verified by combined size exclusion chromatography (SEC) and multiangle laser light scattering (MALLS) analysis. The chemical structures of graft polymers were characterized by FTIR and (1)H NMR. The critical micelle concentration (CMC) of the graft polymer was determined by fluorescence probe technique using pyrene. By controlling the feed ratio of the macroinitiator to the monomer, graft polymers with different branch lengths can be obtained. Using the 3-(4,5 dimethylthiozol-2-yl)-2,5-diphenyl-tetrazolium bromide (MTT) assay, the graft copolymer has been proved to have low cytotoxicity. Based on the amphiphilicity of the graft copolymers, nanoparticular drug delivery systems were prepared by the direct dissolution method and the dialysis method. The anticancer drug Tegafur was encapsulated into polymeric nanoparticles, and in vitro drug release behavior was investigated. Transmission electron microscopy (TEM) images demonstrate that these nanoparticles are regularly spherical in shape. The particle size and distribution of the nanoparticles were measured.

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Nucleophile-initiated and thermal bulk polymerizations of cyclic trimethylene carbonate in the absence of added catalysts

Cited by 13 publications

References 31 publications

Tough and Enzyme‐Degradable Hydrogels

Tough and Enzyme‐Degradable Hydrogels

Organic–Inorganic Interactions in Poly(trimethylene carbonate)–Titania Hybrids

Synthesis and characterization of poly‐α,β‐[N‐(2‐hydroxyethyl)‐L‐aspartamide]‐g‐poly(L‐lactide) biodegradable copolymers as drug carriers

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