US4933408A
Expired / Lapsed
US
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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
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.
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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 |