Hydrophilized polydiorganosiloxane vinylic crosslinkers and uses thereof
First Claim
1. A silicone hydrogel contact lens comprising a crosslinked polymeric material which comprises:
- units of a hydrophilized polydiorganosiloxane vinylic crosslinker which comprises (1) a polydiorganosiloxane polymer chain comprising dimethylsiloxane units and siloxane unit having one methyl substituent and one monovalent C4-C40 organic radical substituent having two to six hydroxyl groups, wherein the molar ratio of the hydrophilized siloxane units to the dimethylsiloxane units is from about 0.035 to about 0.15 and (2) two terminal (meth)acryloyl groups, wherein the polydiorganosiloxane vinylic crosslinker has a number average molecular weight of from about 3000 Daltons to about 80,000 Daltons;
units of a siloxane-containing vinylic monomer; and
units of at least one hydrophilic vinylic monomer,wherein the silicone hydrogel contact lens, when being fully hydrated, has an oxygen permeability (Dk) of at least about 70 barrers, a water content of from about 25% to about 70% by weight, and an elastic modulus of from about 0.2 MPa to about 1.2 MPa.
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Accused Products
Abstract
The invention provides a hydrophilized polydiorganosiloxane vinylic crosslinker which comprises (1) a polydiorganosiloxane polymer chain comprising dimethylsiloxane units and hydrophilized siloxane units each having one methyl substituent and one monovalent C4-C40 organic radical substituent having two to six hydroxyl groups, wherein the molar ratio of the hydrophilized siloxane units to the dimethylsiloxane units is from about 0.035 to about 0.15, and (2) two terminal (meth)acryloyl groups. The hydrophilized polydiorganosiloxane vinylic crosslinker has a number average molecular weight of from about 3000 Daltons to about 80,000 Daltons. The present invention is also related to a silicone hydrogel contact lens, which comprises repeating units derived from a hydrophilized polydiorganosiloxane vinylic crosslinker of the invention.
18 Citations
20 Claims
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1. A silicone hydrogel contact lens comprising a crosslinked polymeric material which comprises:
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units of a hydrophilized polydiorganosiloxane vinylic crosslinker which comprises (1) a polydiorganosiloxane polymer chain comprising dimethylsiloxane units and siloxane unit having one methyl substituent and one monovalent C4-C40 organic radical substituent having two to six hydroxyl groups, wherein the molar ratio of the hydrophilized siloxane units to the dimethylsiloxane units is from about 0.035 to about 0.15 and (2) two terminal (meth)acryloyl groups, wherein the polydiorganosiloxane vinylic crosslinker has a number average molecular weight of from about 3000 Daltons to about 80,000 Daltons; units of a siloxane-containing vinylic monomer; and units of at least one hydrophilic vinylic monomer, wherein the silicone hydrogel contact lens, when being fully hydrated, has an oxygen permeability (Dk) of at least about 70 barrers, a water content of from about 25% to about 70% by weight, and an elastic modulus of from about 0.2 MPa to about 1.2 MPa. - View Dependent Claims (2, 3, 4, 14, 15, 16, 17, 18, 19, 20)
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15. The silicone hydrogel contact lens of claim 14, wherein R4 is a monovalent radical of formula (2).
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16. The silicone hydrogel contact lens of claim 14, wherein R4 is a monovalent radical of formula (3).
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17. The silicone hydrogel contact lens of claim 14, wherein R4 is a monovalent radical of formula (4).
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18. The silicone hydrogel contact lens of claim 14, wherein R4 is a monovalent radical of formula (5).
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19. The silicone hydrogel contact lens of claim 14, wherein R4 is a monovalent radical of formula (6).
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20. The silicone hydrogel contact lens of claim 19, wherein in formula (6) n1 is 3 and q1 is 1.
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5. A method for producing silicone hydrogel contact lenses, comprising the steps of:
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preparing a lens-forming composition which is clear at room temperature and optionally but preferably at a temperature of from about 0 to about 4°
C., wherein the lens-forming composition comprises(a) from about 5% to about 35% by weight of a hydrophilized polydiorganosiloxane vinylic crosslinker of which comprises (1) a polydiorganosiloxane polymer chain comprising dimethylsiloxane units and siloxane unit having one methyl substituent and one monovalent C4-C40 organic radical substituent having two to six hydroxyl groups, wherein the molar ratio of the hydrophilized siloxane units to the dimethylsiloxane units is from about 0.035 to about 0.15 and (2) two terminal (meth)acryloyl groups, wherein the polydiorganosiloxane vinylic crosslinker has a number average molecular weight of from about 3000 Daltons to about 80,000 Daltons, (b) a siloxane-containing vinylic monomer, (c) from about 30% to about 60% by weight of at least one hydrophilic vinylic monomer, and (d) at least one free-radical initiator, provided that the above-listed polymerizable components and any additional polymerizable components add up to 100% by weight; introducing the lens-forming composition into a mold, wherein the mold has a first mold half with a first molding surface defining the anterior surface of a contact lens and a second mold half with a second molding surface defining the posterior surface of the contact lens, wherein said first and second mold halves are configured to receive each other such that a cavity is formed between said first and second molding surfaces; and
curing thermally or actinically the lens-forming composition in the lens mold to form a silicone hydrogel contact lens, wherein the silicone hydrogel contact lens has an oxygen permeability (Dk) of at least about 70 barrers, a water content of from about 25% to about 70% by weight, and an elastic modulus of from about 0.2 MPa to about 1.2 MPa. - View Dependent Claims (6, 7, 8, 9, 10, 11, 12, 13)
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Specification