METHOD OF MAKING A FULLY POLYMERIZED UV BLOCKING SILICONE HYDROGEL LENS
A method of making a substantially fully copolymerized UV blocking hydrogel lens demonstrating sufficient blocking of UV light to meet at least FDA Class II specifications for UV blocking formed from a reaction mixture comprising at least NVP and one other comonomer and a free-radical polymerizable, substituted or unsubstituted, Bis O-hydroxy benzophenone is provided herein.
1 . A method of making a substantially fully polymerized UV blocking hydrogel lens comprising:
polymerizing a monomer reaction mixture of at least NVP and one other comonomer and a free-radical polymerizable, substituted or unsubstituted, Bis O-hydroxy benzophenone to provide a substantially fully polymerized hydrogel ophthalmic device.
2 . The method of claim 1 wherein the substantially fully polymerized hydrogel ophthalmic device has a wettable surface.
3 . The method of claim 1 or 2 wherein the hydrogel ophthalmic device demonstrates sufficient blocking of UV light to meet at least FDA Class II specifications for UV blocking.
4 . The method of claim 1 further wherein the step of polymerizing produces substantially full co-curing of a monomer system component of the monomer reaction mixture to provide a substantially fully copolymerized ophthalmic device.
5 . The method of claim 1 , wherein the free-radical polymerizable, substituted or unsubstituted, Bis O-hydroxy substituted benzophenone is selected from the group consisting of 1,3-Bis(4-benzoyl-3-hydroxyphenoxy)-2-propyl acrylate and 1,3-Bis(4-benzoyl-3-hydroxyphenoxy)-2-propyl methacrylate and mixtures thereof.
6 . The method of claim 1 or 4 , wherein the substantially fully copolymerized ophthalmic device has a water content of about 42.3% to about 59.1% when fully hydrated.
7 . The method of claim 1 or 4 , wherein the substantially fully copolymerized ophthalmic device has a receding contact angle of about 21.
8 . The method of claim 1 or 4 , wherein the substantially fully copolymerized ophthalmic device has an advancing contact angle of between about 29 and about 33.
9 . The method of claim 1 wherein the free-radical polymerizable, substituted or unsubstituted, Bis O-hydroxy benzophenone is functionalized with a free-radical polymerizable mono acrylate or mono methacrylate group.
10 . The method of claim 1 , wherein the substantially fully copolymerized UV blocker containing ophthalmic device has a Wilhelmy Plate area loop of between 0.91 and 1.83.
11 . The method of claim 1 , wherein the monomer mixture further comprises a organosilicon-containing hydrophobic monomer.
12 . The method of claim 11 wherein the organosilicon-containing monomer is present at between 0.1 to 75.8 percent by weight.
13 . The method of claim 11 wherein the organosilicon-containing monomer is present at between 2 to 20 percent by weight.
14 . The method of claim 11 wherein the organosilicon-containing monomer is present at between 5 to 13 percent by weight.
15 . The method of claim 12 wherein the monomer mixture further comprises non-organosilicon-containing hydrophobic monomers.
16 . The method of claim 15 wherein the non-organosilicon-containing hydrophobic monomers are present at about 0 to 60 percent by weight.
17 . The method of claim 15 wherein the non-organosilicon-containing hydrophobic monomers are selected from the group consisting of alkyl acrylates and alkyl methacrylates.
18 . The method of claim 11 wherein the monomer mixture further comprises a bulky monomer selected from the group consisting of methacryloxypropyl tris(trimethylsiloxy)silane (TRIS), pentamethyldisiloxanyl methylmethacrylate, tris(trimethylsiloxy)methacryloxy propylsilane, phenyltretramethyl-disiloxanylethyl acrylate, methyl-di(trimethylsiloxy)methacryloxymethyl silane, 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbamate, 3[tris(trimethylsiloxy)silyl]propyl allyl carbamate, and 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbonate, and mixtures thereof.
19 . The method of claim 18 wherein the bulky monomer is present at greater than 0 to 41.2 percent by weight.
20 . The method of claim 18 herein the bulky monomer is present at greater than 34 to 41 percent by weight.
21 . The method of claim 18 wherein the bulky monomer is present at greater than 25 to 41 percent by weight.
22 . The method of claim 11 wherein the monomer mixture further comprises a hydrophobic crosslinkers selected from the group consisting of ethylene glycol dimethacrylate (EGDMA), allyl methacrylate (AMA) and mixtures thereof.
23 . The method of claim 22 wherein the hydrophobic crosslinkers is present at between 0 to 76 percent by weight.
24 . The method of claim 22 wherein the hydrophobic crosslinkers is present at between 2 to 20 percent by weight.
25 . The method of claim 22 wherein the hydrophobic crosslinkers is present at between 5 to 13 percent by weight.
26 . The method of claim 12 wherein the monomer mixture further comprises a slow reacting hydrophilic monomer in addition to NVP.
27 . The method of claim 26 wherein the slow reacting hydrophilic monomer is 1-vinylazonan-2-one.
28 . The method of claim 12 wherein the monomer mixture further comprises a fast reacting hydrophilic monomer.
29 . The method of claim 28 wherein the fast reacting hydrophilic monomer is selected from the group consisting of unsaturated carboxylic acids, acrylic substituted alcohols, acrylamides and mixtures thereof.
30 . The method of claim 28 wherein the fast reacting hydrophilic monomer is selected from the group consisting of methacrylic acid, acrylic acid, 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, methacrylamide, N,N-dimethylacrylamide (DMA), N-isopropylacrylamide (NIPAM) and mixtures thereof.
31 . The method of claim 28 wherein the fast reacting hydrophilic monomer is present at between 25 to 60 percent by weight.
32 . The method of claim 28 wherein the fast reacting hydrophilic monomer is present at between 30 to 50 percent by weight.
33 . The method of claim 28 wherein the fast reacting hydrophilic monomer is present at between 35 to 45 percent by weight.
34 . The method of claim 26 wherein the slow reacting hydrophilic monomer is present at between 25 to 65 percent by weight.
35 . The method of claim 26 wherein the slow reacting hydrophilic monomer is present at between 30 to 55 percent by weight.
36 . The method of claim 26 wherein the slow reacting hydrophilic monomer is present at between 35 to 45 percent by weight.
37 . The method of claim 1 wherein the monomeric mixture further comprises at least one slow reacting hydrophilic monomer, at least one ethylenically unsaturated hydrophobic monomer and an organic diluent and comprising a combined step of shaping and polymerizing by a method step selected from the group consisting of static casting and spin casting.
38 . The method of claim 37 further comprising a step of exposing the polymerized materials to a solvent selected from the group consisting of water, 2-propanol, etc. and mixes thereof.
39 . The method of claim 37 further comprising a step of autoclaving the polymerized material in water or buffer solution