ACTINICALLY-CROSSLINKABLE SILOXANE-CONTAINING COPOLYMERS
First Claim
1. An actinically crosslinkable prepolymer, which is a RAFT polymerization product of a reactive mixture comprising a polysiloxane crosslinker with two terminal vinyl-groups, a hydrophilic vinylic monomer, a RAFT agent, and a free-radical initiator, wherein the prepolymer comprises:
- (1) polysiloxane crosslinking units derived from the polysiloxane crosslinker both the two terminal vinyl-groups of which undergo the RAFT polymerization;
(2) hydrophilic units derived from a hydrophilic vinylic monomer;
(3) dangling polysiloxane chains with one terminal vinyl group, wherein the dangling polysiloxane chains are derived from the polysiloxane crosslinker one of the two terminal vinyl-groups of which undergoes the RAFT polymerization while the other remains unreacted, wherein the prepolymer is capable of being actinically crosslinked, in the absence of one or more vinylic monomers, to form a silicone hydrogel material.
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Accused Products
Abstract
The invention provide a class of actinically-crosslinkable silicone-containing prepolymers which comprise dangling polysiloxane chains each having a terminal ethylenically-unsaturated group and are obtained in a one-step of RAFT polymerization of a reactive mixture comprising a polysiloxane crosslinker, a hydrophilic vinylic monomer, a RAFT agent, and a free-radical initiator. The present invention is also related to silicone hydrogel contact lenses made from a prepolymer of the invention and methods for making the contact lenses in a cost-effective way and with high consistency and high fidelity to the original lens design.
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Citations
20 Claims
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1. An actinically crosslinkable prepolymer, which is a RAFT polymerization product of a reactive mixture comprising a polysiloxane crosslinker with two terminal vinyl-groups, a hydrophilic vinylic monomer, a RAFT agent, and a free-radical initiator, wherein the prepolymer comprises:
- (1) polysiloxane crosslinking units derived from the polysiloxane crosslinker both the two terminal vinyl-groups of which undergo the RAFT polymerization;
(2) hydrophilic units derived from a hydrophilic vinylic monomer;
(3) dangling polysiloxane chains with one terminal vinyl group, wherein the dangling polysiloxane chains are derived from the polysiloxane crosslinker one of the two terminal vinyl-groups of which undergoes the RAFT polymerization while the other remains unreacted, wherein the prepolymer is capable of being actinically crosslinked, in the absence of one or more vinylic monomers, to form a silicone hydrogel material. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12)
- (1) polysiloxane crosslinking units derived from the polysiloxane crosslinker both the two terminal vinyl-groups of which undergo the RAFT polymerization;
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13. A soft contact lens, comprising:
- a silicone hydrogel material that is obtained by curing a lens-forming material in a mold, wherein the lens-forming material comprises an actinically crosslinkable prepolymer which is a RAFT polymerization product of a reactive mixture comprising a polysiloxane crosslinker with two terminal vinyl-groups, a hydrophilic vinylic monomer, a RAFT agent, and a free-radical initiator, wherein the prepolymer comprises;
(1) polysiloxane crosslinking units derived from the polysiloxane crosslinker both the two terminal vinyl-groups of which undergo the RAFT polymerization;
(2) hydrophilic units derived from a hydrophilic vinylic monomer;
(3) dangling polysiloxane chains with one terminal vinyl group, wherein the dangling polysiloxane chains are derived from the polysiloxane crosslinker one of the two terminal vinyl-groups of which undergoes the RAFT polymerization while the other remains unreacted, wherein the contact lens has at least one property selected from the group consisting of an oxygen permeability of preferably at least about 40 barrers, an elastic modulus of about 1.5 MPa or less, an lonoflux Diffusion Coefficient, D, of at least about 1.5×
10−
6 mm2/min, and a water content of preferably from about 15% to about 70%. - View Dependent Claims (14, 15, 16, 17, 18, 19)
- a silicone hydrogel material that is obtained by curing a lens-forming material in a mold, wherein the lens-forming material comprises an actinically crosslinkable prepolymer which is a RAFT polymerization product of a reactive mixture comprising a polysiloxane crosslinker with two terminal vinyl-groups, a hydrophilic vinylic monomer, a RAFT agent, and a free-radical initiator, wherein the prepolymer comprises;
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20. A method for producing soft contact lenses, comprising the steps of:
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providing a mold for making a soft contact lens, 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; introduce a lens-forming material into the cavity, wherein the lens-forming material comprises an actinically crosslinkable prepolymer which is a RAFT polymerization product of a reactive mixture comprising a polysiloxane crosslinker with two terminal vinyl-groups, a hydrophilic vinylic monomer, a RAFT agent, and a free-radical initiator, wherein the prepolymer comprises (1) polysiloxane crosslinking units derived from the polysiloxane crosslinker both the two terminal vinyl-groups of which undergo the RAFT polymerization, (2) hydrophilic units derived from a hydrophilic vinylic monomer, and (3) dangling polysiloxane chains with one terminal vinyl group, wherein the dangling polysiloxane chains are derived from the polysiloxane crosslinker one of the two terminal vinyl-groups of which undergoes the RAFT polymerization while the other remains unreacted; and actinically irradiating the lens forming material in the cavity to form a contact lens.
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Specification