Synthesis and polymerization of new pyrrolidone-containing methacrylate monomers

Iskander, George M.; Baker, Lucy E.; Wiley, Dianne E.; Davis, Thomas P.

doi:10.1016/s0032-3861(98)00002-0

Cited by 25 publications

(31 citation statements)

References 6 publications

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“…3 and Table 3, entries 4 and 5). These values can compete with typical Δ T values of modified polyoxazolines54, 55 and are even lower as those described for glycol modified41 and pyrrolidine containing methacrylates 56. A similar observation was made with the block copolymers with low‐degree of polymerization.…”

Section: Resultssupporting

confidence: 68%

The thermo responsive behavior of glycol functionalized ring opening metathesis polymers

Bauer

Slugovc

2010

J. Polym. Sci. A Polym. Chem.

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Herein a further step towards self‐assembly of polymers exhibiting a lower critical solution temperature (LCST) effect is presented. Ring opening metathesis polymerization has been chosen as polymerization method because of its high functional group tolerance, the reliability and the capability to synthesize different polymer architectures such as self‐assembling block copolymers, which currently gain much attention in nanotechnology, electronics, and biomedical applications. In a first step, the polymerization behavior of oligo(ethylene glycol) monoalkyl ether [HO(CH2CH2O)nR, n = 2, 3 and 5–9, R = Et or Me] substituted norbornene derivatives with [(H2IMes) (py)Cl2Ru(3‐phenyl‐indenylid‐1‐ene)] (H2IMes = N,N‐bis(mesityl) 4,5‐dihydroimidazol‐2‐yl, py = pyridine) was assessed. While monomers bearing short oligo(ethylene glycol)monoalkyl ether groups (n = 2 or 3) allowed for controlled polymerization, the monomers featuring long oligo(ethylene glycol)monoalkyl ether groups could not be polymerized in a controlled manner. Only polymers prepared from endo,exo‐bicyclo[2.2.1]hept‐5‐ene‐2,3‐dicarboxylic acid, bis[2‐[2‐(2‐ethoxyethoxy)ethoxy]ethyl] ester (2) showed satisfactory water solubility and a LCST of about 25 °C. This temperature is largely independent from the molecular weight and the macromolecular architecture of the polymers as it was revealed from determination of the LCST of a series of statistic and block copolymers incorporating less‐polar comonomers. The molecular weight affects the complete transition value (ΔT), which is rising with increasing degree of polymerization. ΔT values smaller than 1 °C can be obtained with statistic copolymers of 2 with less polar monomers like endo,exo‐bicyclo[2.2.1]hept‐5‐ene‐2,3‐dicarboxylic acid dimethyl ester. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 2098–2108, 2010

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Section: Resultssupporting

confidence: 68%

The thermo responsive behavior of glycol functionalized ring opening metathesis polymers

Bauer

Slugovc

2010

J. Polym. Sci. A Polym. Chem.

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“…In particular, PNMEP exhibits inverse solubility behaviour as already noted above. 26,40 At around ambient temperature, the pyrrolidone ring forms hydrogen bonds with water that confer aqueous solubility, despite the relatively hydrophobic methacrylic backbone. However, such hydrogen bonding is disrupted on heating to a sufficiently high temperature, causing PNMEP to precipitate from aqueous solution.…”

Section: Introductionmentioning

confidence: 99%

End-group ionisation enables the use of poly(N-(2-methacryloyloxy)ethyl pyrrolidone) as an electrosteric stabiliser block for polymerisation-induced self-assembly in aqueous media

et al. 2019

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“…Controlled polymerization methods have allowed clearer determination of LCST behavior of many polymers due to its ability to reduce the dispersity when compared to conventional radical polymerization. For example, pyrrolidone‐based polymers had no LCST or broad LCST transitions when synthesized by conventional radical polymerization . Later work with controlled radical polymerization (CRP) techniques showed a clear LCST at 52.8–71.5 °C for N ‐(2‐methacryloyloxyethyl)‐pyrrolidone (MAEPYR) homopolymers and 34.3–50.9 °C for its statistical copolymers with 9‐(4‐vinylbenzyl)−9H‐carbazole (VBK).…”

Section: Introductionmentioning

confidence: 99%

Using controlled radical polymerization to confirm the lower critical solution temperature of an N‐(alkoxyalkyl) acrylamide polymer in aqueous solution

Savelyeva

Marić

2014

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

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NANOCOMPOSITE On page 3506, Adriana C. Pinheiro, Adriana C. A. Casagrande, and Osvaldo L. Casa-grande, Jr., report linear low density polyethylene (LLDPE) nanocomposites containing different types of nanofiller (TiO 2 , MWCNT, expanded graphite, and boehmite) prepared with a tandem catalyst system composed of {Tp Ms }NiCl and Cp 2 ZrCl 2 with only ethylene as the monomer. Among the nanofillers utilized, carbon nanotubes and boehmite can nucleate LLDPE crystallization, as indicated by increased crystallization temperature. Furthermore, the presence of these nanofillers in the LLDPE matrix results in substantial improvement of the storage modulus as compared to neat LLDPE. The TEM images of LLDPE nanocomposites containing boehmite and MWCNT reveal homogeneous dispersion of these nanofillers into the LLDPE matrix. report on nanoparticles obtained after complexa-tion of Ru(NH 3) 3 Cl 3 with hydroxyl groups of dendritic copolymers of tert-butyl-glycidyl-ether and glycidol using silver tetrafluoroborate as a dechlorination agent. Visualization is performed by cryogenic transmission electron microscopy using a Libra 120 Zeiss microscope , operated at an acceleration voltage of 120 kV, at the Leibniz Institute of Polymer Research Dresden.

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Synthesis and polymerization of new pyrrolidone-containing methacrylate monomers

Cited by 25 publications

References 6 publications

The thermo responsive behavior of glycol functionalized ring opening metathesis polymers

The thermo responsive behavior of glycol functionalized ring opening metathesis polymers

End-group ionisation enables the use of poly(N-(2-methacryloyloxy)ethyl pyrrolidone) as an electrosteric stabiliser block for polymerisation-induced self-assembly in aqueous media

Using controlled radical polymerization to confirm the lower critical solution temperature of an N‐(alkoxyalkyl) acrylamide polymer in aqueous solution

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