Patent US4661573A successfully refreshed from Google Patents.
US4661573A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Lens composition articles and method of manufacture
Assignee: Barnes Hind Inc
•
Filing: 1986-04-14
•
Granted: 1987-04-28
•
Expires: 2006-04-14
Abstract
Abstract New copolymer composition, methods for processing the copolymers into optical devices and articles resulting therefrom, especially intraocular and contact lenses having outstanding extended wear and daily wear properties. The composition comprises, in weight percent: from 3% to 35% polyfluoroalkyl acrylate; from 45% to 65% acryloxyalkylpolysiloxane; 1% to 15% acryloxyalkylsilanol; 2% to 20% polyacryloxyalkylpolysiloxane; 2% to 15% polyol polyacrylate and 2% to 15% polymerizable ethylenically unsaturated monomeric wetting agent such as acrylic acid. The composition may also contain 0 to 15% acrylic acid ester of a monohydric alcohol having no more than 20 carbon atoms and from 0.05% to about 2.0% of a free radical initiator.
Inventors
- 👤 Donald J. Ratkowski
- 👤 William J. Burke
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 22:01
CPC Classifications
C; C08; C08F; C08F230/00; C08F230/04; C08F230/08; G; G02; G02B; G02B1/00; G02B1/04; G02B1/041; G02B1/043
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
309 words
A copolymer composition, especially suited for fabricating optical lenses, comprising a copolymer of copolymerized comonomers containing: (a) about 45% to about 65% by weight of a siloxy substituted ester of acrylic or methacrylic acid having the structure: ##STR9## wherein R=CH 3 -- or H--; X=C 1 -C 6 alkyl, cyclohexyl, phenyl or Z; Y=C 1 -C 6 alkyl, cyclohexyl, phenyl or Z; Z= ##STR10## R1=C 1 -C 6 alkyl, cyclohexyl, or phenyl; m=1-3; R2=C 1 -C 6 alkyl, cyclohexyl, or phenyl; n=1-5; R3=C 1 -C 6 alkyl, cyclohexyl, or phenyl; p=1-3; R4=C 1 -C 6 alkyl or cyclohexyl; (b) about 3% to about 35% by weight of a polyfluoroalkyl acrylate having no more than 20 fluorine atoms and the structure: ##STR11## wherein: R=H or CH 3 ; A=H or E; and E=a polyfluoroalkyl group; (c) about 1% to about 15% by weight of an acryloxyalkylsilanol having the structure: ##STR12## wherein: R=CH 3 -- or H--; X, Y=C 1 -C 6 alkyl; phenyl or Z; Z= ##STR13## n=1-5 m=1-3 p=1-3 R1=C 1 -C 6 alkyl, cyclohexyl, or phenyl; R2=C 1 -C 6 alkyl, cyclohexyl, or phenyl; R3=C 1 -C 6 alkyl, cyclohexyl, or phenyl; (d) about 2% to about 20% by weight of a polyacryloxyalkylpolysiloxane having the structure: ##STR14## wherein: R=CH 3 -- or H--; m=0-3; n=1-5; X=C 1 -C 6 alkyl, cyclohexyl, phenyl or Z; Y=C 1 -C 6 alkyl, cyclohexyl, phenyl or Z; and Z= ##STR15## p=1-3; R1=C 1 -C 6 alkyl, cyclohexyl, or phenyl; R2=C 1 -C 6 alkyl, cyclohexyl, or phenyl; and R3=C 1 -C 6 alkyl, cyclohexyl, or phenyl; (e) about 2% to 15% of a polyol polyacrylate; (f) about 2% to about 15% of an ethylenically unsaturated polymerizable wetting agent; and (g) zero to about 15% by weight of an acrylic acid ester of a monohydric alcohol having no more than 20 carbon atoms.
Claim 2
Dependent Claim
309 words
A copolymer composition, especially suited for fabricating optical lenses, comprising a copolymer of copolymerized comonomers containing: (a) about 45% to about 65% by weight of a siloxy substituted ester of acrylic or methacrylic acid having the structure: ##STR9## wherein R=CH 3 -- or H--; X=C 1 -C 6 alkyl, cyclohexyl, phenyl or Z; Y=C 1 -C 6 alkyl, cyclohexyl, phenyl or Z; Z= ##STR10## R1=C 1 -C 6 alkyl, cyclohexyl, or phenyl; m=1-3; R2=C 1 -C 6 alkyl, cyclohexyl, or phenyl; n=1-5; R3=C 1 -C 6 alkyl, cyclohexyl, or phenyl; p=1-3; R4=C 1 -C 6 alkyl or cyclohexyl; (b) about 3% to about 35% by weight of a polyfluoroalkyl acrylate having no more than 20 fluorine atoms and the structure: ##STR11## wherein: R=H or CH 3 ; A=H or E; and E=a polyfluoroalkyl group; (c) about 1% to about 15% by weight of an acryloxyalkylsilanol having the structure: ##STR12## wherein: R=CH 3 -- or H--; X, Y=C 1 -C 6 alkyl; phenyl or Z; Z= ##STR13## n=1-5 m=1-3 p=1-3 R1=C 1 -C 6 alkyl, cyclohexyl, or phenyl; R2=C 1 -C 6 alkyl, cyclohexyl, or phenyl; R3=C 1 -C 6 alkyl, cyclohexyl, or phenyl; (d) about 2% to about 20% by weight of a polyacryloxyalkylpolysiloxane having the structure: ##STR14## wherein: R=CH 3 -- or H--; m=0-3; n=1-5; X=C 1 -C 6 alkyl, cyclohexyl, phenyl or Z; Y=C 1 -C 6 alkyl, cyclohexyl, phenyl or Z; and Z= ##STR15## p=1-3; R1=C 1 -C 6 alkyl, cyclohexyl, or phenyl; R2=C 1 -C 6 alkyl, cyclohexyl, or phenyl; and R3=C 1 -C 6 alkyl, cyclohexyl, or phenyl; (e) about 2% to 15% of a polyol polyacrylate; (f) about 2% to about 15% of an ethylenically unsaturated polymerizable wetting agent; and (g) zero to about 15% by weight of an acrylic acid ester of a monohydric alcohol having no more than 20 carbon atoms.
Claim 3
Dependent Claim
26 words
A copolymr composition according to claim 1 containing from about 48% to about 55% by weight of said siloxy substituted ester of acrylic or methacrylic acid.
Claim 4
Dependent Claim
25 words
A copolymer composition according to claim 2 in which said siloxy substituted ester is selected from the group consisting of γ-methacryloxypropyl-tris(trimethylsiloxy)-silane; γ-acryloxypropyl-tris(trimethylsiloxy) silane; and 5-methacryloxypropyl-1,1,1-trimethyl-3,3,5,5-tetrakis(trimethylsiloxy)trisiloxane.
Claim 5
Dependent Claim
20 words
A copolymer composition according to claim 1 containing from about 8% to about 25% by weight of said polyfluoroalkyl acrylate.
Claim 6
Dependent Claim
45 words
A copolymer composition according to claim 4 in which said polyfluoroalkyl acrylate is selected from the group consisting of: 2,2,2-trifluoroethyl methacrylate, hexafluoroisopropyl methacrylate; 1,1-dihydroperfluoro 2,2-dimethylpropyl acrylate; 1,1-dihydroperfluorobutyl methacrylate; 1-trifluoromethylethyl acrylate; nonafluorocyclohexyl acrylate; 1,1-dihydroperfluorooctyl methacrylate; 2,2,3,3-tetrafluoropropyl methacrylate; 1,1-dihydroperfluoropropyl acrylate; 1,1-dihydroperfluorononyl methacrylate; 2-(N-ethylperfluorooctanesulfamido)ethyl methacrylate; and 2,2,2-trifluoroethyl-α-carboxymethyl acrylate.
Claim 7
Dependent Claim
19 words
A copolymer composition according to claim 1 containing from about 3% to about 13% by weight of said acryloxyalkylsilanol.
Claim 8
Dependent Claim
29 words
A copolymer composition according to claim 6 in which said acryloxyalkylsilanol is selected from the group consisting of bis(trimethylsiloxy)-γ-methacryloxypropylsilanol, methyl (trimethylsiloxy)-methacryloxymethylsilanol, methyl(trimethylsiloxy)-β-methacryloxyethylsilanol, methyl(trimethylsiloxy)-γ-methacryloxypropylsilanol, bis(trimethylsiloxy)-β-methacryloxyethylsilanol, bis(trimethylsiloxy)-methylacryloxymethylsilanol, (trimethylsiloxy)-(pentamethyldisiloxanyl)-methacryloxymethylsilanol, (trimethylsiloxy)-(pentamethyldisiloxanyl)-β-methacryloxymethylsilanol, and (trimethylsiloxy)-(pentamethyldisiloxanyl)-γ-methacryloxypropylsilanol.
Claim 9
Dependent Claim
19 words
A copolymer composition according to claim 1 containing from about 3% to about 15% by weight of said polyacryloxyalkylpolysiloxane.
Claim 10
Dependent Claim
31 words
A copolymer composition according to claim 8 in which said polyacryloxyalkylpolysiloxane is selected from the group consisting of 1,3-bis(methacryloxypropyl)-1,1,3,3-tetrakis (trimethylsiloxy) disiloxane, 1,3-bis(acryloxymethyl)-1,1,3,3-tetrakis (trimethylsiloxy) disiloxane, 1,3-bis(methacryloxypropyl)-1,1,3,3-tetrakis (triethylsiloxy) disiloxane, and 1,5-bis(methacryloxymethyl)-1,1,3,3,5,5-hexa (trimethylsiloxy) trisiloxane.
Claim 11
Dependent Claim
20 words
A copolymer composition according to claim 1 containing from about 5% to about 12% by weight of said polyol polyacrylate.
Claim 12
Dependent Claim
31 words
A copolymer composition according to claim 10 in which said polyol polyacrylate is selected from the group consisting of ethylene glycol dimethacrylate, trimethylolpropane triacrylate, diethyleneglycol dimethacrylate, glycerol trimethacrylate and tetramethyleneglycol dimethacrylate.
Claim 13
Dependent Claim
23 words
A copolymer composition according to claim 1 containing from about 5% to about 12% by weight of said ethylenically unsaturated polymerizable wetting agent.
Claim 14
Dependent Claim
40 words
A copolymer composition according to claim 12 in which said wetting agent is selected from the group consisting of acrylic acid; methacrylic acid; itaconic acid; N-vinylpyrrolidone; hydroxyethyl methacrylate; N-(1,1-dimethyl-3-oxybutyl)-2-acrylamide; glycerol monomethacrylate; N,N-dimethylaminomethyl methacrylate; 2-methoxyethyl acrylate; N,N-dimethylacrylamide; acrylamide and 2-carboxyethyl methacrylate.
Claim 15
Dependent Claim
22 words
A copolymer composition according to claim 1 containing up to about 10% by weight of an acrylic acid ester of monohydric alcohol.
Claim 16
Dependent Claim
42 words
A copolymer composition according to claim 14 in which said acrylic acid ester is selected from the group consisting of methyl methacryate; stearyl methacrylate; cyclohexyl acrylate; isopropyl methacrylate; isoborynl acrylate; cyclopentadienyl methacrylate; phenylacrylate; benzyl methacrylate; 2-methyl-propyl methacrylate; isopropyl acrylate and methyl-α-carbomethoxy acrylate.
Claim 17
Dependent Claim
20 words
A copolymer composition according to claim 8 containing from about 5% to about 12% by weight of said polyol polyacrylate.
Claim 18
Dependent Claim
31 words
A copolymer composition according to claim 16 in which said polyol polyacrylate is selected from the group consisting of ethylene glycol dimethacrylate, trimethylolpropane triacrylate, diethyleneglycol dimethacrylate, glycerol trimethacrylate and tetramethyleneglycol dimethacrylate.
Claim 19
Dependent Claim
26 words
A copolymer composition according to claim 17 in which said polyacryloxyalkylpolysiloxane is selected from the group consisting of 1,3-bis(methacryloxypropyl)-1,1,3,3-tetrakis (trimethylsiloxy)disiloxane, 1,3-bis(acryloxymethyl)-1,1,3,3-tetrakis(trimethylsiloxy)disiloxane, 1,3-bis(methacryloxypropyl)-1,1,3,3-tetrakis(triethylsiloxy)disiloxane, and 1,5-bis(methacryloxymethyl)-1,1,3,5,5-hexa (trimethylsiloxy) trisiloxane.
Claim 20
Dependent Claim
51 words
A copolymer composition according to claim 1 containing from about 0.05% to about 2% by weight of an initiator selected from the group consisting of 2,2'-azobis(isobutyronitrile); 2,2'-azobis(2,4-dimethylvaleronitrile); 2,2'-azobis (methylbutyronitrile)-acetyl peroxide; lauroyl peroxide; benzoyl peroxide; tertiary-butyl peroxypivalate; diisopropyl peroxycarbonate; tertiary-butyl peroctoate; methyl ethyl ketone peroxide; di(2-phenoxyethyl) peroxydicarbonate; and di(2-phenoxyethyl)methyl ethyl ketone peroxide.
Claim 21
Dependent Claim
105 words
A copolymer composition according to claim 1 containing by weight percent: from about 48% to about 55% of a siloxy substituted ester of acrylic or methacrylic acid; from about 8% to about 25% of a polyfluoroalkyl acrylate; from about 3% to about 13% of an acryloxyalkylsilanol; from about 3% to about 15% of a polyacryloxyalkylpolysiloxane; from about 5% to about 12% of a polyol polyacrylate; from about 5% to about 12% of one or more polymerizable, ethylenically unsaturated monomeric wetting agents; up to 10% of an acrylic acid ester of a monohydric alcohol; and from 0.1% to about 1.5% of a free radical polymerization initiator.
Claim 22
Dependent Claim
95 words
A copolymer composition according to claim 20 containing by weight percent: from about 48% to about 55% of methacryloxypropyltris-(trimethylsiloxy) silane; from about 8% to about 25% of a monomer selected from the group consisting of 2,2,2-trifluoroethyl methacrylate, 1,1-dihydroperfluoro methacrylate, and 2-N-ethylperfluorooctanesulfonamidoethyl methacrylate; from about 3% to about 13% of bis(trimethylsiloxy)-γ-methacryloxypropylsilanol; from about 3% to about 15% of 1,3-bis(methacryloxypropyl)-1,1,3,3-tetrakis(trimethylsiloxy) disiloxane; from about 5% to about 12% of ethylene glycol dimethacrylate; from about 5% to about 12% of methacrylate acid; up to 10% of methylmethacrylate of N-vinyl pyrrolidone; and from 0.1% up to about 1.5% of 2,2'-azobis(isobutyronitrile).
Claim 23
Dependent Claim
19 words
As a new article of manufacture, an optical lens fabricated from the copolymer of copolymerized comonomers of claim 1.
Claim 24
Dependent Claim
14 words
An article of manufacture according to claim 22 comprising an extended wear contact lens.
Claim 25
Dependent Claim
20 words
As a new article of manufacture, a contact lens button fabricated from the copolymer of copolymerized comonomers of claim 1.
Claim 26
Dependent Claim
16 words
As a new article of manufacture, a contact lens formed from the button of claim 24.
Claim 27
Dependent Claim
19 words
As a new article of manufacture, an optical lens fabricated from the copolymer of copolymerized comonomers of claim 20.
Claim 28
Dependent Claim
14 words
An article of manufacture according to claim 26 comprising an extended wear contact lens.
Claim 29
Dependent Claim
20 words
As a new article of manufacture, a contact lens button fabricated from the copolymer of copolymerized comonomers of claim 20.
Claim 30
Dependent Claim
16 words
As a new article of manufacture, a contact lens formed from the button of claim 28.
Claim 31
Dependent Claim
19 words
As a new article of manufacture, an optical lens fabricated from the copolymer of copolymerized comonomers of claim 21.
Claim 32
Dependent Claim
14 words
An article of manufacture according to claim 30 comprising an extended wear contact lens.
Claim 33
Dependent Claim
20 words
As a new article of manufacture, a contact lens button fabricated from the copolymer of copolymerized comonomers of claim 21.
Claim 34
Dependent Claim
16 words
As a new article of manufacture, a contact lens formed from the button of claim 32.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-04-27 | 1990-10-27 | 1991-04-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-04-27 | 1994-10-27 | 1995-04-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-04-27 | 1998-10-27 | 1999-04-28 | $7700.00 | Window Closed / Lapsed |