New MethacryloxyN-Vinyl-2-pyrrolidinone- and Lactone-Based Macromers

Tarabić, Milica; Ranucci, Elisabetta

doi:10.1002/1616-5195(20010601)1:4<126::aid-mabi126>3.0.co;2-7

Cited by 4 publications

(3 citation statements)

References 11 publications

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“…The synthesis of HEMA‐Im (Scheme ) was performed as already reported 9,11. Briefly, HEMA was treated with CDI in alcohol‐free chloroform at room temperature and without added catalysts.…”

Section: Resultsmentioning

confidence: 99%

2‐[(1‐Imidazolyl)formyloxy]ethyl Methacrylate as Selective Methacryloylating Agent: Kinetics of Reaction with Model Alcohols and Amines

Ranucci

Grigolini

Ferruti

2003

Macromolecular Bioscience

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The kinetics of the coupling reactions of 2‐[(1‐imidazolyl)formyloxy]ethyl methacrylate (HEMA‐Im) with model primary and secondary alcohols and amines have been investigated both in the absence and in the presence of imidazole and triethylamine as catalysts. In the absence of added catalysts, alcohols either reacted very sluggishly or did not react at all with HEMA‐Im, but amines reacted completely in relatively short times. In the presence of catalysts, both primary and secondary alcohols underwent coupling reactions with HEMA‐Im, the former about ten times faster than the latter. Imidazole was a more effective catalyst than triethylamine. HEMA‐Im's ability to discriminate between amino and hydroxyl groups was tested with 4‐amino‐1‐butanol: the 1H NMR analysis of the reaction product confirmed 100% selectivity towards the amino group. It was therefore concluded that HEMA‐Im is a highly selective methacryloylating agent, with a synthetic potential for preparing multifunctional monomers and polymers.Reaction curves for HEMA‐Im with EtOH and PriOH at 37 °C in the presence of imidazole (HEM5 and HEM6) and triethylamine (HEM7 and HEM8).magnified imageReaction curves for HEMA‐Im with EtOH and PriOH at 37 °C in the presence of imidazole (HEM5 and HEM6) and triethylamine (HEM7 and HEM8).

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Section: Resultsmentioning

confidence: 99%

2‐[(1‐Imidazolyl)formyloxy]ethyl Methacrylate as Selective Methacryloylating Agent: Kinetics of Reaction with Model Alcohols and Amines

Ranucci

Grigolini

Ferruti

2003

Macromolecular Bioscience

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“…Similarly to the preparation of end‐hydroxylated PVP oligomers previously mentioned, PVP oligomers bearing at one terminus ester residues were prepared by radical polymerization of NVP in the presence of aliphatic esters acting in the meantime as solvents and chain transfer agents. The chain transfer involved one hydrogen atom α to the ester function . Compared with ATRP or RAFT, this synthetic method gave end‐functionalized oligomers with broader molecular weight distribution, but had the merit of being very simple and easily scaled‐up.…”

Section: Introductionmentioning

confidence: 99%

One-step synthesis of poly(lactic-co-glycolic acid)-g-poly-1-vinylpyrrolidin-2-one copolymers

Ranucci

Capuano

Manfredi

et al. 2016

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

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The radical polymerization of 1-vinylpyrrolidin-2-one (NVP) in poly(lactic-co-glycolic acid) (PLGA) 50:50 at 100 8C leads to amphiphilic PLGA-g-PVP copolymers. Their composition is determined by FT-IR spectroscopy. Thermogravimetric analyses agree with FT-IR determinations. Saponification of the PLGA-g-PVP polyester portion allows isolating the PVP side chains and measuring their molecular weight, from which the average chain transfer constant (C T ) of the PLGA units is estimated. The MALDI-TOF spectra of PVP reveal the presence at one chain end of residues of either glycolic acid-or lactic acidor lactic/glycolic acid dimers, trimers and one tetramer, the other terminal being hydrogen. This unequivocally demonstrates that grafting occurred. Accordingly, the orthogonal solvent pair ethyl acetate-methanol, while separating the components of PLGA/PVP intimate mixtures, fails to separate pure PVP or PLGA from the reaction products. All PLGA-g-PVP and PLGA/PLGA-g-PVP blends, but not PLGA/PVP blends, give long-time stable dispersions in water.

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“…The initiator was prepared by an efficient one-step process (Scheme 1). At first, 2-hydroxyethylmethacrylate (HEMA), which has been used as a coinitiator in some studies, 14,16,[23][24][25][26] was used as a reagent, but we found that the chemical modification reaction was impossible to control, and the characterizations proven there were some transesterification reactions. When 2-allyloxyethanol (AEOH) was used as alcohol, the initiator was successfully prepared without side reactions.…”

Section: Introductionmentioning

confidence: 99%

Preparation of unsaturated poly(ε‐caprolactone) with a new titanium alkoxide initiator

Xia¹,

Zerroukhi²,

Chalamet³

et al. 2008

J of Applied Polymer Sci

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Titanium alkoxides are widely used in the ring-opening polymerization of e-caprolactone. In this study, functional poly(e-caprolactone) was synthesized with a new titanium initiator by a two-step procedure: First, the titanium initiator, with an unsaturated group, was prepared by a classical organic reaction between 2-hydroxyethylmethacrylate or 2-allyloxyethanol with titanium tetrapropoxide; then, we initiated the polymerization of the e-caprolactone monomer in a glass reactor or twinscrew extruder. By means of NMR spectroscopy, the structures of the initiators and polymers were determined.When 2-hydroxyethylmethacrylate was used, there was a side reaction (transesterification) during the preparation of the initiator, and so it was impossible to obtain the expected product. With 2-allyloxyethanol, the designed titanium initiator was synthesized with high purity, and the allyl moiety remained intact after the polymerization of e-caprolactone.

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New MethacryloxyN-Vinyl-2-pyrrolidinone- and Lactone-Based Macromers

Abstract: Monomer conversion (0) and degree of polymerization ( 6 ) of d-VL macromer as a function of time.

Cited by 4 publications

References 11 publications

2‐[(1‐Imidazolyl)formyloxy]ethyl Methacrylate as Selective Methacryloylating Agent: Kinetics of Reaction with Model Alcohols and Amines

2‐[(1‐Imidazolyl)formyloxy]ethyl Methacrylate as Selective Methacryloylating Agent: Kinetics of Reaction with Model Alcohols and Amines

One-step synthesis of poly(lactic-co-glycolic acid)-g-poly-1-vinylpyrrolidin-2-one copolymers

Preparation of unsaturated poly(ε‐caprolactone) with a new titanium alkoxide initiator

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