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Fluorinated poly(ETHER)s end-capped with polymerizable cationic hydrophilic groups

a technology of fluorinated poly(ether) and cationic hydrophilic groups, which is applied in the preparation of carbamic acid derivatives, chemistry apparatus and processes, and organic chemistry, etc. it can solve the problems of uncomfortable lenses and non-wetting, and achieve high oxygen permeability, impart hydrophilicity to the fpe, and low modulus

Inactive Publication Date: 2012-04-19
BARCLAYS BANK PLC AS SUCCESSOR AGENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The modified fluorinated poly(ether)s result in optically clear, hydrophilic contact lenses with improved compatibility and oxygen permeability, combining the comfort of hydrogels with the oxygen permeability of fluorinated materials.

Problems solved by technology

FPEs functionalized with polymerizable methacrylate end-groups have been pursued for use in contact lens materials to take advantage of the high Dk but have not been incorporated into a commercial lens presumably due to the very hydrophobic nature of the fluorinated backbone and resulting incompatibility with other monomers and / or additives resulting in a non-wetting, uncomfortable lens.

Method used

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  • Fluorinated poly(ETHER)s end-capped with polymerizable cationic hydrophilic groups
  • Fluorinated poly(ETHER)s end-capped with polymerizable cationic hydrophilic groups
  • Fluorinated poly(ETHER)s end-capped with polymerizable cationic hydrophilic groups

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examples

[0058]All solvents and reagents are obtained from Sigma-Aldrich, Milwaukee, Wis., and used as received with the exception of the fluorinated poly(ether)s, under trade name ZDOL, obtained from Solvay Solexis, Thorofare, N.J., which is used without further purification. The monomers 2-hydroxyethyl methacrylate and 1-vinyl-2-pyrrolidone are purified using standard techniques.

Analytical Measurements

[0059]NMR: 1H-Nuclear Magnetic Resonance (NMR) characterization is carried out using a 400 MHz Varian spectrometer using standard techniques in the art. Samples are dissolved in chloroform-d (99.8 atom % D), unless otherwise noted. Chemical shifts are determined by assigning the residual chloroform peak at 7.25 ppm. Peak areas and proton ratios are determined by integration of baseline separated peaks. Splitting patterns (s=singlet, d=doublet, t=triplet, q=quartet, m=multiplet, br=broad) and coupling constants (J / Hz) are reported when present and clearly distinguishable.

[0060]SEC: Size Exclus...

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Abstract

The present invention relates to polymeric compositions useful in the manufacture of biocompatible medical devices. More particularly, the present invention relates to certain cationic monomers capable of polymerization to form polymeric compositions having desirable physical characteristics useful in the manufacture of ophthalmic devices. The polymer compositions comprise polymerized fluorinated polyether monomer end-capped with ethylenically unsaturated cationic hydrophilic groups.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application is a divisional of application Ser. No. 11 / 480,170, filed Jun. 30, 2006, the contents of which are incorporated herein by reference.FIELD[0002]The present invention relates to polymeric compositions useful in the manufacture of biocompatible medical devices. More particularly, the present invention relates to certain fluorinated poly(ether)s end-capped with polymerizable cationic hydrophilic groups capable of polymerization to form polymeric compositions having desirable physical characteristics useful in the manufacture of ophthalmic devices.BACKGROUND AND SUMMARY[0003]Fluorinated poly(ether)s (FPEs) are a unique class of chemically inert, low modulus materials that have characteristically high oxygen permeability. FPEs functionalized with polymerizable methacrylate end-groups have been pursued for use in contact lens materials to take advantage of the high Dk but have not been incorporated into a commercial lens presuma...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C08F236/20C07C271/22
CPCC08G65/007C08G2650/48C08G65/33306
Inventor SCHORZMAN, DEREKKUNZIER, JAY
Owner BARCLAYS BANK PLC AS SUCCESSOR AGENT