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US4933408A Expired / Lapsed US ⏱️ 0.0 years remaining

Vinylic macromers containing perfluoropolyalkyl ether and polyalkyl ether segments, polymers and opthalmic devices made therefrom

Assignee: Ciba Vision Corp
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Filing: 1989-01-11
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Granted: 1990-06-12
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Expires: 2009-01-11
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Abstract

Abstract The instant invention relates to vinylic macromers containing perfluoropolyalkylether and polyalkylether segments, polymers and ophthalmic devices such as intraocular implants and contact lenses and particularly soft hydrogel contact lenses made therefrom.

Inventors

  • 👤 Merrill Goldenberg

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 16:19
CPC Classifications
G; G02; G02B; G02B1/00; G02B1/04; G02B1/041; G02B1/043; C; C08; C08F; C08F290/00; C08F290/02; C08F290/06; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/48; C08G18/50; C08G18/5003; C08G18/5015; C08G18/70; C08G18/81; C08G18/8108; C08G18/8141; C08G18/815; C08G18/8158; C08G65/00; C08G65/002; C08G65/005; C08G65/007; C08G2210/00; Y; Y10; Y10S; Y10S525/00; Y10S525/937

Claims Analysis

Total Claims: 28
Claim 1
Independent Claim 365 words
A macromer containing perfluoropolyalkylether and polyalkylether segments and ethylenically unsaturated moieties, having the formula I, more specifically as seen in formulas Ia to ID, E-T-L-Q-X-Z-X-Q-L-T-E, (Ia) E-T-L-Q-X-Z-X-Q-L, (Ib) E-T-L-Q-X-G-X-Q-L-T-E, or (Ic) E-T-L-Q-X-G-X-Q-L (Id) wherein Z is --(C a F 2a O) b --CF 2 --, where a is 1 to 4, b is 2 to 200; X is a direct bond, --CH 2 --, --CH 2 OCH 2 CHOHCH 2 --, --CH 2 (OCH 2 CH 2 ) y -- or carbonyl where y is 1 to 10 and where in each case the carbon atom is attached to Z or G; Q is a direct bond or --ACONH--R--NHCO-- where A is oxa or imino and R is a divalent aliphatic group having from 2 to 14 carbon atoms, a divalent 5-or 6-membered cycloaliphatic group having 5 to 14 carbon atoms or an arylene group having 6 to 14 carbon atoms; L is --A(C m H 2m O) n C m H 2m AY-- or L 1 where Y is a direct bond or H and m is 2 to 4 or mixtures thereof and n is 5 to 100, where A is attached to Q; T is --COHN--R 5 A-- or --CONH--R--NHCOOR 5 A-- or --CONH--R--NHCO--A-- or --R 5 A-- or direct bond where the carbonyl group is attached to L, where R 5 is alkylene or hydroxy-substituted alkylene of 2 to 15 carbon atoms and R is as above; ##STR8## where R 1 is hydrogen or methyl, and R 2 is hydrogen, methyl or --COOR 3 where R 3 is hydrogen or alkyl of 1 to 4 carbon atoms with the proviso that, when R 1 is methyl, R 2 is hydrogen, R 4 is hydrogen or methyl and G is --(C a F 2a O) b --CF 2 [CH 2 --OCONH--R--NHCOOCH 2 CF 2 (OC a F 2a ) b ] x or --(C a F 2a O) b --CF 2 [CH 2 --NHCONH--R--NHCONHCH 2 CF 2 (OC a F 2a ) b ] x where x is 1 to 3; ##STR9## where n 1 is 5 to 100, z is 1 to 10 and Y is a direct bond or H.
Claim 2
Dependent Claim 365 words
A macromer containing perfluoropolyalkylether and polyalkylether segments and ethylenically unsaturated moieties, having the formula I, more specifically as seen in formulas Ia to ID, E-T-L-Q-X-Z-X-Q-L-T-E, (Ia) E-T-L-Q-X-Z-X-Q-L, (Ib) E-T-L-Q-X-G-X-Q-L-T-E, or (Ic) E-T-L-Q-X-G-X-Q-L (Id) wherein Z is --(C a F 2a O) b --CF 2 --, where a is 1 to 4, b is 2 to 200; X is a direct bond, --CH 2 --, --CH 2 OCH 2 CHOHCH 2 --, --CH 2 (OCH 2 CH 2 ) y -- or carbonyl where y is 1 to 10 and where in each case the carbon atom is attached to Z or G; Q is a direct bond or --ACONH--R--NHCO-- where A is oxa or imino and R is a divalent aliphatic group having from 2 to 14 carbon atoms, a divalent 5-or 6-membered cycloaliphatic group having 5 to 14 carbon atoms or an arylene group having 6 to 14 carbon atoms; L is --A(C m H 2m O) n C m H 2m AY-- or L 1 where Y is a direct bond or H and m is 2 to 4 or mixtures thereof and n is 5 to 100, where A is attached to Q; T is --COHN--R 5 A-- or --CONH--R--NHCOOR 5 A-- or --CONH--R--NHCO--A-- or --R 5 A-- or direct bond where the carbonyl group is attached to L, where R 5 is alkylene or hydroxy-substituted alkylene of 2 to 15 carbon atoms and R is as above; ##STR8## where R 1 is hydrogen or methyl, and R 2 is hydrogen, methyl or --COOR 3 where R 3 is hydrogen or alkyl of 1 to 4 carbon atoms with the proviso that, when R 1 is methyl, R 2 is hydrogen, R 4 is hydrogen or methyl and G is --(C a F 2a O) b --CF 2 [CH 2 --OCONH--R--NHCOOCH 2 CF 2 (OC a F 2a ) b ] x or --(C a F 2a O) b --CF 2 [CH 2 --NHCONH--R--NHCONHCH 2 CF 2 (OC a F 2a ) b ] x where x is 1 to 3; ##STR9## where n 1 is 5 to 100, z is 1 to 10 and Y is a direct bond or H.
Claim 3
Dependent Claim 28 words
A macromer according to claim 1 wherein X is --CH 2 -- or --CH 2 (OCH 2 CH 2 ) y -- where y is 1 to 2.
Claim 4
Dependent Claim 30 words
A macromer according to claim 1 wherein Q is --ACONH--R--NHCO-- where R is the radical derived from hexane-1,6-diisocyanate, trimethyl-hexane-1,6-diisocyanate, tetramethylenediisocyanate, phenylene-1,4-diisocyanate, toluene-2,4-diisocyanate, toluene-2,6-diisocyanate, m- or p-tetramethylxylenediisocyanate, isophorone diisocyanate or cyclohexane-1,4-diisocyanate.
Claim 5
Dependent Claim 16 words
A macromer according to claim 3 wherein R is the divalent radical derived from isophorone diisocyanate.
Claim 6
Dependent Claim 20 words
A macromer according to claim 1 where in Z, a is 1 or 2, and b is 3 to 50.
Claim 7
Dependent Claim 35 words
A macromer according to claim 1 where L is --O(C m H 2m O) n C m H 2m O-- where m is 2 or a mixture of 2 and 3, and n is 9-50.
Claim 8
Dependent Claim 21 words
A macromer according to claim 1 where T is --CONH--R 5 A-- and R 5 is ethylene and A is oxa.
Claim 9
Dependent Claim 30 words
A macromer according to claim 1 where T is --CONH--R--NHCOOR 5 A-- and R 5 is ethylene and R is the radical derived from isophorone diisocyanate and A is oxa.
Claim 10
Dependent Claim 19 words
A macromer according to claim 1 where E is ##STR10## R 1 is methyl and R 2 is hydrogen.
Claim 11
Dependent Claim 18 words
A macromer according to claim 1 where E is ##STR11## R 1 and R 2 are both hydrogen.
Claim 12
Dependent Claim 21 words
A macromer according to claim 1 where in G, x is 1 and R is a radical derived from isophorone diisocyanate.
Claim 13
Dependent Claim 33 words
A macromer according to claim 1 where in L 1 , A is oxa, R is a radical derived from isophorone diisocyanate, z is 1 to 5 and n is 5 to 100.
Claim 14
Dependent Claim 11 words
A macromer according to claim 1 having the formula (Ia) E-T-L-Q-X-Z-X-Q-L-T-E.
Claim 15
Dependent Claim 68 words
A macromer according to claim 13 wherein E is --CO--C(CH 3 )═CH 2 , T is --CONH--CH 2 CH 2 --O--, L is --O(C 2 H 4 O) n C 2 H 4 O-- where n is 19-25, Q is --OCONH--isophorone--NHCO--, X is --CH 2 --, and Z is --CF 2 O(C 2 F 4 O) r --(CF 2 O) s --CF 2 where r/s is about 0.7.
Claim 16
Dependent Claim 14 words
A crosslinked hompolymerization product of a macromer E-T-L-Q-X-Z-X-Q-L-T-E or E-T-L-Q-X-G-X-Q-L-T-E according to claim 1.
Claim 17
Dependent Claim 14 words
A crosslinked copolymerization product of the macromer E-T-L-Q-X-Z-X-Q-L-T-E and E-T-L-Q-X-Z-X-Q-L according to claim 1.
Claim 18
Dependent Claim 74 words
A crosslinked product according to claim 15 wherein the macromer is E-T-L-Q-X-Z-X-Q-L-T-E where E is --CO--C(CH 3 )═CH 2 , T is --CONH--CH 2 CH 2 --O--, L is --O(C 2 H 4 O) n C 2 H 4 O-- where n is 19-25, Q is --OCONH--isophorone--NHCO--, X is --CH 2 --, and Z is --CF 2 O(C 2 F 4 O) r --(CF 2 O) s --CF 2 where r/s is about 0.7.
Claim 19
Dependent Claim 10 words
An ophthalmic device prepared from the product of claim 15.
Claim 20
Dependent Claim 10 words
An ophthalmic device prepared from the product of claim 16.
Claim 21
Dependent Claim 10 words
An ophthalmic device prepared from the product of claim 17.
Claim 22
Dependent Claim 19 words
A product according to claim 16 where greater than 1% of the material is derived from the macromer E-T-L-Q-X-Z-X-Q-L-T-E.
Claim 23
Dependent Claim 19 words
A product according to claim 16 where greater than 10% of the material is derived from the macromer E-T-L-Q-X-Z-X-Q-L-T-E.
Claim 24
Dependent Claim 19 words
A product according to claim 16 where greater than 20% of the material is derived from the macromer E-T-L-Q-X-Z-X-Q-L-T-E.
Claim 25
Dependent Claim 19 words
A product according to claim 16 where greater than 30% of the material is derived from the macromer E-T-L-Q-X-Z-X-Q-L-T-E.
Claim 26
Dependent Claim 7 words
A contact lens according to claim 18.
Claim 27
Dependent Claim 7 words
A contact lens according to claim 19.
Claim 28
Dependent Claim 7 words
A contact lens according to claim 20.

References Cited (Backward Citations)

US3639524A Cited
US3841985A Cited
US3985697A Cited
US3929741A Cited
EP0084406A1 Cited
US4440918A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1993-06-11 1993-12-11 1994-06-12 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1997-06-11 1997-12-11 1998-06-12 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2001-06-11 2001-12-11 2002-06-12 $7700.00 Window Closed / Lapsed

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