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Novel polysiloxane-polyurethanes and contact lens thereof

Assignee: Novartis Corp
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Filing: 1988-11-03
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Granted: 1990-10-09
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Expires: 2008-11-03
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Abstract

Abstract A novel polysiloxane polyurethane is described which is obtained by reaction of an isocyanate capped polysiloxane prepolymer with a polysiloxane-disilanol and which contains O-silyl-urethane linkages. The novel polysiloxane-polyurethanes are useful as oxygen permeable membranes or films, as bandages and drug carriers, for example in transdermal drug delivery, and especially as highly oxygen permeable, soft contact lenses.

Inventors

  • 👤 Paul Harisiades

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 21:50
CPC Classifications
A; A61; A61K; A61K9/00; A61K9/70; A61K9/7023; A61K9/703; A61K9/7038; A61K9/7046; A61K9/7069; A61L; A61L15/00; A61L15/16; A61L15/22; A61L15/26; C; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/10; C08G18/28; C08G18/40; C08G18/61; G; G02; G02B; G02B1/00; G02B1/04; G02B1/041; G02B1/043

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 331 words
A siloxane-urethane polymer, suitable for use as an oxygen permeable membrane or an ophthalmic device, having based on total urethane groups 50 to 80% of --C--NH--COO--C-- groups and 50 and 20% of --C--NH--COO--Si-- groups, which consists essentially of the polymerization product of (a) 80-95% weight (based on the total polymer) of a poly-isocyanate capped, linear or branched polysiloxane prepolymer, having a molecular weight of about 1000 to about 10,000 and containing at least one isocyanate group per 3000 molecular weight unit of polysiloxane, said isocyanate groups being attached to the polysiloxane through urethane linkages, said polysiloxane prepolymer having the structure A 1 , A 2 and A 3 ##STR8## wherein: R 1 is a linear or branched alkylene group with 2-6 carbon atoms or a polyoxyalkylene group of structures ##STR9## wherein R 3 is hydrogen or methyl and p is an integer from 1-50; R 2 , R a , R b , R c , R d , R e , R f , R g , R h , R i , R j , R k are independently methyl or phenyl; x 1 , x 2 are integers from 1 to 500 with the proviso that the sum of x 1 +x 2 is 12 to 1,000; y 1 is 0 to 4 and y 2 is 2 to 5 with the proviso that the respective ratios of ##EQU3## are not greater than 70, ##STR10## wherein T 1 is A 1 from which X 1 removed, and T 3 is A 3 from which X 3 is removed, R 4 is a di-radical obtained by removing NCO-groups from an aliphatic, cycloaliphatic or aromatic di-isocyanate; and (b) 20-50% by weight (based on the total polymer) of a linear polydialkyl- or polydiphenyl-siloxane disilanol in ##STR11## having a molecular weight from about 240 to about 1000 and containing terminal siloxanol groups, where, n is 2-50 and E a and E b are alkyl of 1 to 4 carbon atoms or phenyl.
Claim 2
Dependent Claim 331 words
A siloxane-urethane polymer, suitable for use as an oxygen permeable membrane or an ophthalmic device, having based on total urethane groups 50 to 80% of --C--NH--COO--C-- groups and 50 and 20% of --C--NH--COO--Si-- groups, which consists essentially of the polymerization product of (a) 80-95% weight (based on the total polymer) of a poly-isocyanate capped, linear or branched polysiloxane prepolymer, having a molecular weight of about 1000 to about 10,000 and containing at least one isocyanate group per 3000 molecular weight unit of polysiloxane, said isocyanate groups being attached to the polysiloxane through urethane linkages, said polysiloxane prepolymer having the structure A 1 , A 2 and A 3 ##STR8## wherein: R 1 is a linear or branched alkylene group with 2-6 carbon atoms or a polyoxyalkylene group of structures ##STR9## wherein R 3 is hydrogen or methyl and p is an integer from 1-50; R 2 , R a , R b , R c , R d , R e , R f , R g , R h , R i , R j , R k are independently methyl or phenyl; x 1 , x 2 are integers from 1 to 500 with the proviso that the sum of x 1 +x 2 is 12 to 1,000; y 1 is 0 to 4 and y 2 is 2 to 5 with the proviso that the respective ratios of ##EQU3## are not greater than 70, ##STR10## wherein T 1 is A 1 from which X 1 removed, and T 3 is A 3 from which X 3 is removed, R 4 is a di-radical obtained by removing NCO-groups from an aliphatic, cycloaliphatic or aromatic di-isocyanate; and (b) 20-50% by weight (based on the total polymer) of a linear polydialkyl- or polydiphenyl-siloxane disilanol in ##STR11## having a molecular weight from about 240 to about 1000 and containing terminal siloxanol groups, where, n is 2-50 and E a and E b are alkyl of 1 to 4 carbon atoms or phenyl.
Claim 3
Dependent Claim 15 words
A polymer according to claim 1 which is in the form of an ophthalmic device.
Claim 4
Dependent Claim 15 words
A polymer according to claim 2 which is in the form of a contact lens.
Claim 5
Dependent Claim 20 words
A polymer according to claim 1 wherein the prepolymer of component (a) has structure A 1 or A 2 .
Claim 6
Dependent Claim 17 words
A polymer according to claim 4 wherein the prepolymer of component (a) has structure A 1 .
Claim 7
Dependent Claim 103 words
A polymer according to claim 1 wherein the prepolymer of component (a) has structure A 1 or A 2 , R 1 is alkylene of 3 or 4 carbon atoms, R 2 , R a , R b , R c , R d , R f , R g , R h , R i , R j and R k are each methyl, x 1 +x 2 is 12 to 100, y 1 is 0 to 2, y 2 is 2 to 3, and R 4 is a diradical of an aliphatic or cycloaliphatic diisocyanate with 6 to 10 carbon atoms.
Claim 8
Dependent Claim 81 words
A polymer according to claim 1 wherein the prepolymer of component (a) has structure A 1 , A 2 or A 3 in which R 4 is a diradical obtained by removing the --NCO groups from a diisocyanate selected from the group consisting of ethylene diisocyanate, 1,2-diisocyanatopropane, 1,3-diioscyanatopropane, 1,6-diiso-cyanatohexane, 1,6-diisocyanato-2,2-4-(2,4,4)-trimethylhexane, 2,2'-diisocyanatodiethyl fumarate, 1,2-, 1,3-, 1,5-, 1,6-, 1,7-, 1,8-, 2,7- and 2,3-diisocyanatomaphthalene; 2,4- and 2,7-diisocyanato-1-methylnaphthalene; 1,4-diisocyanatobiphenyl; 1,2-diisocyanatocyclohexane, 1,3-diisocyanatocyclohexane, 1,4-diisocyanatobenzene, bis-(4-isocyanatocyclohexanyl)methane, bis(4-isocyanato-phenyl)methane, 1,2 and 1,4-toluene diisocyanate, 3,3-dichloro-4,4'-diisocyanatobiphenyl, hydrogenated toluene diisocyanate, and isophorone diisocycanate.
Claim 9
Dependent Claim 14 words
A polymer according to claim 7 wherein the isocyanate is isophorone diisocyanate or 1,6-diisocyanato-2,2,4-(2,4,4-)-trimethylhexane.
Claim 10
Dependent Claim 21 words
A polymer according to claim 1 where in the siloxane disilanol of component (b) E a and E b are methyl.
Claim 11
Dependent Claim 17 words
A polymer according to claim 9 where in the siloxane silanol of component (b) n is 3-6.

References Cited (Backward Citations)

US3179622A Cited
US3562352A Cited
US4202807A Cited
US4292423A Cited
JPS57156005A Cited
US4692476A Cited
US4644046A Cited
US4590224A Cited
JPS6383121A Cited
US4740533A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1993-10-08 1994-04-09 1994-10-09 $2000.00 Window Closed / Lapsed
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