VISIBLE LIGHT ABSORBERS FOR OPHTHALMIC DEVICES
A visible light absorbing azo compound having a structure of Formula I: wherein X 1 , X 2 , X 3 , Y and Z are as defined herein, and ophthalmic devices formed therefrom.
1 . A visible light absorbing azo compound having a structure of Formula I:
wherein X 1 , X 2 and X 3 are independently hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a vinyl group or an allyl group; Y is hydrogen, a substituted or unsubstituted alkyl group, or a vinyl group or an allyl group; and Z is hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a vinyl group or an allyl group, wherein at least one of X 1 , X 2 , X 3 , Y and Z is a vinyl group or an allyl group.
2 . The visible light absorbing azo compound according to claim 1 , wherein X 1 and X 2 are hydrogen, X 3 is a vinyl group, Y is a C 1 to C 6 alkyl group and Z is a hydrogen.
3 . The visible light absorbing azo compound according to claim 1 , wherein X 1 and X 2 are hydrogen, X 3 is a C 1 to C 6 alkyl group, Y is a C 1 to C 6 alkyl group and Z is an allyl group.
4 . The visible light absorbing azo compound according to claim 1 , wherein each of X 1 , X 2 and X 3 are independently a C 1 to C 6 alkyl group, Y is a vinyl group and Z is a substituted or unsubstituted alkoxy group.
5 . The visible light absorbing azo compound according to claim 1 , wherein X 1 and X 2 are hydrogen, X 3 is a C 1 to C 6 alkyl group, Y is a vinyl group or an allyl group and Z is a C 1 to C 6 alkoxy group.
6 . The visible light absorbing azo compound according to claim 1 , wherein each of X 1 , X 2 and X 3 are independently a C 1 to C 6 alkyl group, Y is a vinyl group or an allyl group and Z is a hydrogen.
7 . The visible light absorbing azo compound according to claim 1 , wherein one of X 1 , X 2 and X 3 is a vinyl group or an allyl group, and the other ones of X 1 , X 2 and X 3 are hydrogen, Y is a vinyl group or an allyl group and Z is a hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted alkoxy group.
8 . An ophthalmic device which is a polymerization product of a monomeric mixture comprising:
(a) a visible light absorbing azo compound having a structure of Formula I:
wherein X 1 , X 2 and X 3 are independently hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a vinyl group or an allyl group; Y is hydrogen, a substituted or unsubstituted alkyl group, or a vinyl group or an allyl group; and Z is hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a vinyl group or an allyl group, wherein at least one of X 1 , X 2 , X 3 , Y and Z is a vinyl group or an allyl group; and
(b) one or more ophthalmic device-forming monomers.
9 . The ophthalmic device according to claim 8 , wherein in the visible light absorbing azo compound X 1 and X 2 are hydrogen, X 3 is a vinyl group, Y is a C 1 to C 6 alkyl group and Z is a hydrogen.
10 . The ophthalmic device according to claim 8 , wherein in the visible light absorbing azo compound X 1 and X 2 are hydrogen, X 3 is a C 1 to C 6 alkyl group, Y is a C 1 to C 6 alkyl group and Z is an allyl group.
11 . The ophthalmic device according to claim 8 , wherein in the visible light absorbing azo compound each of X 1 , X 2 and X 3 are independently a C 1 to C 6 alkyl group, Y is a vinyl group and Z is a substituted or unsubstituted alkoxy group.
12 . The ophthalmic device according to claim 8 , wherein in the visible light absorbing azo compound X 1 and X 2 are hydrogen, X 3 is a C 1 to C 6 alkyl group, Y is a vinyl group or an allyl group and Z is a C 1 to C 6 alkoxy group.
13 . The ophthalmic device according to claim 8 , wherein in the visible light absorbing azo compound each of X 1 , X 2 and X 3 are independently a C 1 to C 6 alkyl group, Y is a vinyl group or an allyl group and Z is a hydrogen.
14 . The ophthalmic device according to claim 8 , wherein in the visible light absorbing azo compound one of X 1 , X 2 and X 3 is a vinyl group or an allyl group, and the other ones of X 1 , X 2 and X 3 are hydrogen, Y is a vinyl group or an allyl group and Z is a hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted alkoxy group.
15 . The ophthalmic device according to claim 8 , wherein the monomeric mixture comprises about 0.005 wt. % to about 0.5 wt. %, based on the total weight of the monomeric mixture, of the visible light absorber.
16 . The ophthalmic device according to claim 8 , wherein the one or more ophthalmic device-forming monomers comprise one or more of styrene, a hydrophilic monomer, a polyethylene glycol methacrylate monomer, and a heterocyclic monomer having an ethylenically unsaturated reactive end group.
17 . The ophthalmic device according to claim 8 , wherein the ophthalmic device absorbs light between about 380 and about 500 nanometers (nm) wavelength.
18 . The ophthalmic device according to claim 17 , wherein the light is blue light.
19 . The ophthalmic device according to claim 8 , which is one of an intraocular lens, intraocular implant and a contact lens.
20 . A method for making an ophthalmic device, comprising:
(a) providing a monomeric mixture comprising:
(i) a visible light absorbing azo compound having a structure of Formula I:
wherein X 1 , X 2 and X 3 are independently hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a vinyl group or an allyl group; Y is hydrogen, a substituted or unsubstituted alkyl group, or a vinyl group or an allyl group; and Z is hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a vinyl group or an allyl group, wherein at least one of X 1 , X 2 , X 3 , Y and Z is a vinyl group or an allyl group, and
(ii) one or more ophthalmic device-forming monomers; and
(b) subjecting the monomeric mixture to polymerization conditions to provide an ophthalmic device.