Silicone hydrogels comprising n-vinyl amides and hydroxyalkyl (meth)acrylates or (meth)acrylamides
AssigneeJohnson & Johnson Vision Care, Inc.
InventorsAzaam Alli, Douglas G. Vanderlaan, James D. Ford, Scott L. Joslin
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Abstract
The present invention relates to a process comprising the steps of reacting a reactive mixture comprising at least one silicone-containing component, at least one hydrophilic component, and at least one diluent to form an ophthalmic device having an advancing contact angle of less than about 80°; and contacting the ophthalmic device with an aqueous extraction solution at an elevated extraction temperature, wherein said at least one diluent has a boiling point at least about 10° higher than said extraction temperature.
Claims46
A silicone hydrogel formed from a reaction mixture comprising,
- (a) from about 37 to 70 wt % of at least one slow reacting monomer selected from the group consisting of N-vinylamide monomers of Formula I, vinyl pyrrolidones of Formula II-IV, and N-vinyl piperidones of Formula V:
- wherein in Formula I through V R is H or methyl;
- R1, R2, R3, R6, R7, R10, and R11 are independently selected from the group consisting of H, CH3, CH2CH3, CH2CH2CH3, C(CH3)2;
- R4 and R8 are independently selected from the group consisting of CH2, CHCH3 and C(CH3);
- R5 is selected from H, methyl, ethyl;
- and
- R9 is selected from CH═CH2, CCH3═CH2, and CH═CHCH3;
- (b) at least one mono (meth)acryloxyalkyl polydialkylsiloxane monomer of Formula VII or the styryl polydialkylsiloxane monomer of Formula VIII:
- wherein in Formula VI through VIII R12 is H or methyl;
- X is O or NR16;
- each R14 is independently a C1 to C4 alkyl which may be fluorine substituted, or phenyl;
- R15 is a C1 to C4 alkyl;
- R13 is a divalent alkyl group, which may further be functionalized with a group selected from the group consisting of ether groups, hydroxyl groups, carbamate groups and combinations thereof;
- a is 3 to 50;
- R16 is selected from H, C1-C4, which may be further substituted with one or more hydroxyl groups;
- (c) at least one hydroxyalkyl (meth)acrylate or (meth)acrylamide monomer of Formula IX or a styryl compound of Formula X
- wherein R17 is H or methyl,
- Q is O or NR16, R16 is a H, or C1 to C4 alkyl, which may be further substituted with at least one OH;
- R18 is selected from C2-C4 mono or dihydroxy substituted alkyl, and poly(ethylene glycol) having 1-10 repeating units;
- wherein said at least one hydroxyalkyl (meth)acrylate or (meth)acrylamide monomer and said slow reacting monomer are present in mole percents which form a molar ratio between 0.15 and 0.4;
- and
- (d) at least one crosslinking monomer.
Dependencies are inferred from the claim text.