CA2343159A1 - Perfluoropolyalkylpolyether polymers for ophthalmic applications - Google Patents

Perfluoropolyalkylpolyether polymers for ophthalmic applications Download PDF

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Publication number
CA2343159A1
CA2343159A1 CA002343159A CA2343159A CA2343159A1 CA 2343159 A1 CA2343159 A1 CA 2343159A1 CA 002343159 A CA002343159 A CA 002343159A CA 2343159 A CA2343159 A CA 2343159A CA 2343159 A1 CA2343159 A1 CA 2343159A1
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CA
Canada
Prior art keywords
units
group
polymer according
pfpe
formula
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002343159A
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French (fr)
Other versions
CA2343159C (en
Inventor
Hassan Chaouk
Timothy Charles Hughes
John Stuart Wilkie
Gordon Francis Meijs
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Commonwealth Scientific and Industrial Research Organization CSIRO
Novartis AG
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Individual
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Publication of CA2343159A1 publication Critical patent/CA2343159A1/en
Application granted granted Critical
Publication of CA2343159C publication Critical patent/CA2343159C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses
    • G02B1/043—Contact lenses
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5003—Polyethers having heteroatoms other than oxygen having halogens
    • C08G18/5015—Polyethers having heteroatoms other than oxygen having halogens having fluorine atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/81—Unsaturated isocyanates or isothiocyanates
    • C08G18/8108—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group
    • C08G18/8116—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/002—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds
    • C08G65/005—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens
    • C08G65/007—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02—Polyalkylene oxides

Abstract

The present invention relates to polymers comprising one or more perfluoralkylpolyether units and one or more different charged units, to a process for producing such polymers in non-porous or particularly in porous form and to mouldings composed thereof. The novel polymers have an improved wettability and cell growth ability and are thus useful, for example, for the manufacture of biomedical devices, in particular ophthalmic devices.

Claims (24)

1. A polymer comprising one or more perfluoroalkylpolyether (PFPE) units and one or more charged units selected from the group consisting of zwitter-ionic units and a mixture of anionic and cationic units.
2. A polymer according to claim 1, wherein the charged units are zwitter-ionic units.
3. A polymer according to claim 1 or 2, wherein the PFPE units are of formula -OCH2CF2O (CF2CF2O )x(CF2O )y CF2CH2O- (1) wherein the CF2CF2O and CF2O units may be randomly distributed or distributed as blocks throughout the chain and wherein x and y may be the same or different such that the molecular weight of the perfluorinated polyether is in the range of from 242 to 8000, preferably from 242 to 4000.
4. A polymer according to claim 3, wherein x is from 1 to 20, and y is from 1 to 25.
5. A polymer according to any one of claims 1 to 4, wherein the charged units each correspond to formula , (2), wherein either (i) two of the three variables R5, R6 and R7 are hydrogen and the third one is hydrogen, carboxy, carboxymethyl or C1-C4-alkyl; or (ii) R5 and R6 together with the adjacent carbon atoms form a 5- to 7-membered cycloaliphatic or heterocyclic ring and R7 is hydrogen; or (iii) R5 and R6 are each hydrogen and R7 and A together with the adjacent carbon atoms form a 5- to 7-membered cycloaliphatic or heterocyclic ring; or (iv) R5 and R7 are each hydrogen and R6 and A together with the adjacent carbon atom form a 5- to 7-membered cycloaliphatic or heterocyclic ring;

A is a direct bond or a a carbonyl, carbonate, amide, ester, dicarboanhydride, dicarboimide, urea or urethane functional group; and Z is an aliphatic, cycloaliphatic or heterocyclic moiety comprising an anionic group or a cationic group or one anionic and one cationic group each.
6. A polymer according to claim 5, wherein the cationic group is a monovalent group -NRR'R"+ or a bivalent group -NRR'+-, wherein R, R' and R" may be the same or different and are each independently of the other hydrogen or C1-C24-alkyl, and the anionic group is a monovalent group -COO-, -SO3- , -OSO3-, -OPO3H- -OPO2 -OR11 or bivalent -O-PO2 -O-, wherein R11 is C1-C12-alkyl.
7. A polymer according to any one of claims 1 to 6, wherein the charged units are zwitter-ionic units of formula wherein A is a direct bond or a carbonyl, ester or amide functional group, and Z is C2-C12-alkyl which is substituted by -NRR'R"+, -COO-, -SO3- , -OSO3- , -OPO2 -OR11 or and/or is interrupted by a group -NRR'+ - or -O-PO2 -O-, R, R' and R" are each independently of the other hydrogen or C1-C12-alkyl and R11 is C2-C8-alkyl, with the proviso that Z contains one anionic and one cationic group each.
8. A polymer according to claim 7, wherein -A-Z is a radical of formula -C(O)O-alk-NRR'+-alk'-An- (3a) or -C(O)O-alk-O-PO2--O-alk'-NRR'R"+ (3b), R, R' and R" may be the same or different and are each independently of the other hydrogen or C1-C12-alkyl, alk and alk' may be the same or different and are each independently of the other C1-C12-alkylene, and An- is an anionic group -COO, -SO3, -OSO3 , -OPO2-OR11 or -OPO3H- wherein R11 is C2-C8-alkyl.
9. A polymer according to any one of claims 1 to 8, wherein the PFPE units are derived from a macromonomer of formula Q-(PFPE- L)n-1-PFPE-Q (4), Q-B-(L-B)n- T (5), or Q-PFPE-L-M-L-PFPE-Q (6), wherein Q may be the same or different and is a polymerizable group;
PFPE is a divalent residue of formula (1) according to claim 1;
L is a difunctional linking group;
n is at least 1;
each B may be the same or different and is a difunctional block of molecular weight in the range of from 100 to 4000 and wherein at least one B is a perfluorinated polyether of formula (1) according to claim 1;
T is a univalent terminal group which is not polymerisable by free radicals but which may contain other functionality; and M is a residue from a difunctional polymer or copolymer having a molecular weight in the range of from 180 to 6000 and comprising silicone repeat units of formula (7), wherein R1 and R1' may be the same or different and are selected from the group consisting of hydrogen, alkyl, aryl and halosubstituted alkyl.
10. A polymer according to claim 9, wherein the PFPE units are derived from a macromonomer of formula (4), wherein n is in the range of from 2 to 5, L is a bivalent residue -C(O)-NH-R3-NH-C(O)- of a diisocyanate wherein R3 is alkylene, arylene, alkylenearylene, arylenealkylene or arylenealkylenearylene having up to 14 carbon atoms or a saturated divalent cycloaliphatic group having 6 to 14 carbon atoms, and Q is a compound of formula P1 -(Y)m-(R2-X1)p- (8), wherein P1 is alkenyl of 2 to 4 carbon atoms, Y is -COO-, R2 is alkylene of 1 to 4 carbon atoms, X1 is -NHCO- and m and p are each 1.
11. A polymer according to any one of claims 1 to 10, wherein the charged units are derived from one or more different monomers of formula wherein R5, R6, R7, A and Z are defined as in claim 5, or from a suitable precursor thereof.
12. A polymer according to claim 11, wherein the PFPE macromonomer is present in the polymerization mixture in an amount of 99.5 to 70 % by weight, and the charged monomer is present in an amount of 0.5 to 30 % by weight, each based on the total of polymerizable material.
13. A process for the preparation of a polymer according to any one of claims 1 to 12, comprising the step of copolymerizing one or more macromonomers comprising at least one PFPE unit and at least one polymerizable charged monomer or a precursor thereof, and, if a charged monomer precursor has been used, converting the precursor units into charged units after the copolymerization reaction.
14. A polymer obtainable by the process according to claim 13.
15. A polymer according to any one of claims 1 to 12, which is porous and has a water contents, when fully swollen in water, which is higher than that of the same polymer if polymerized under conventional conditions.
16. A polymer according to claim 15, wherein the water contents, when fully swollen in water, is from 5 to 60 % by weight.
17. A process for the production of a porous polymer according to claim 15 or 16, comprising the steps of:

i) forming a mixture comprising a polymerizable component and an organic solvent wherein the polymerizable component comprises at least one PFPE macromonomer and one charged monomer;
ii) polymerizing said mixture wherein immediately after the polymerization of said mixture at least a substantial proportion of said organic solvent is in the form of a discrete phase and wherein said discrete organic solvent phase forms an interpenetrating network throughout the mixture or is dispersed throughout the mixture; and iii) removing the discrete organic solvent phase.
18. A process according to claim 17, wherein the organic solvent is a C1-C3-alkanol.
19. A process for the production of a porous polymer according to claim 15 or 16, comprising the steps of:
i) dispersing a porogen in a continuous phase of a polymerizable component wherein said polymerizable component comprises at least one PFPE macromonomer and one charged monomer, and wherein said porogen is an optionally substituted poly(alkylene)glycol;
ii) polymerising said dispersion; and iii) removing the porogen from the porous polymer.
20. A process according to claim 19, wherein the porogen is a polyalkylene glycol.
21. A moulding comprising a polymer according to any one of claims 1 to 12 and 14 to 16.
22. A moulding according to claim 21, which is a biomedical device, in particular an ophthalmic device.
23. A moulding according to claim 21, which is an ocular prostheses, in particular a corneal implant.
24. Use of a polymer according to any one of claims 1 to 12 and 14 to 16 for the manufacture of an ophthalmic device or an ocular prostheses.
CA2343159A 1998-09-15 1999-09-13 Perfluoropolyalkylpolyether polymers for ophthalmic applications Expired - Fee Related CA2343159C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP98117421.2 1998-09-15
EP98117421 1998-09-15
PCT/EP1999/006767 WO2000015686A1 (en) 1998-09-15 1999-09-13 Polymers

Publications (2)

Publication Number Publication Date
CA2343159A1 true CA2343159A1 (en) 2000-03-23
CA2343159C CA2343159C (en) 2010-06-22

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Family Applications (1)

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CA2343159A Expired - Fee Related CA2343159C (en) 1998-09-15 1999-09-13 Perfluoropolyalkylpolyether polymers for ophthalmic applications

Country Status (14)

Country Link
US (1) US6225367B1 (en)
EP (1) EP1161476B1 (en)
JP (1) JP2002524628A (en)
CN (1) CN1318076A (en)
AT (1) ATE356157T1 (en)
AU (1) AU754125C (en)
BR (1) BR9913694A (en)
CA (1) CA2343159C (en)
DE (1) DE69935457T2 (en)
ES (1) ES2284268T3 (en)
NO (1) NO20011292L (en)
TW (1) TWI230712B (en)
WO (1) WO2000015686A1 (en)
ZA (1) ZA200102072B (en)

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CA2343159C (en) 2010-06-22
JP2002524628A (en) 2002-08-06
EP1161476A1 (en) 2001-12-12
AU754125B2 (en) 2002-11-07
DE69935457D1 (en) 2007-04-19
NO20011292D0 (en) 2001-03-14
WO2000015686A1 (en) 2000-03-23
BR9913694A (en) 2001-06-05
ATE356157T1 (en) 2007-03-15
EP1161476B1 (en) 2007-03-07
AU6190699A (en) 2000-04-03
DE69935457T2 (en) 2007-11-15
ZA200102072B (en) 2001-10-30
TWI230712B (en) 2005-04-11
US6225367B1 (en) 2001-05-01
NO20011292L (en) 2001-05-14
CN1318076A (en) 2001-10-17
ES2284268T3 (en) 2007-11-01
AU754125C (en) 2006-08-31

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