Polymerizable fused tricyclic compounds as absorbers of UV and visible light
Described are polymerizable fused tricyclic compounds of formula I: wherein R 1 , R 2 , R 3 , m, n, t, and rings B, C, and D are as defined herein. The compounds absorb various wavelengths of ultraviolet and/or visible light (such as high energy visible light) and are suitable for incorporation in a variety of products, such as biomedical devices and ophthalmic devices.
1 . An ophthalmic device that is a polymerization reaction product of a reactive mixture comprising: (a) a monomer suitable for making the ophthalmic device; and (b) a compound of formula II:
wherein m and n are independently 0, 1, 2, 3, or 4;
R 1 and R 2 are independently at each occurrence H, an optional substituent, or —Y—P g , or two adjacent R 1 or R 2 groups, together with the atoms to which they are attached, combine to form a cycloalkyl or aryl ring optionally substituted with —Y—P g ;
EWG at each occurrence is independently an electron withdrawing group;
P g at each occurrence is independently a polymerizable group; and
Y at each occurrence is independently a linking group;
wherein the compound of formula II contains at least one P g group.
2 . The ophthalmic device of claim 1 wherein the monomer suitable for making the device is selected from a hydrophilic component, a hydrophobic component, a silicone-containing component, or a mixture of two or more thereof.
3 . The ophthalmic device of claim 1 that is a conventional hydrogel or a silicone hydrogel.
4 . The ophthalmic device of claim 1 that is an intraocular lens or a soft contact lens.
5 . The ophthalmic device of claim 1 wherein m and n are independently 0 or 1.
6 . The ophthalmic device of claim 1 wherein R 1 is H, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 thioalkyl, C 3 -C 7 cycloalkyl, aryl, halo, hydroxy, amino, NR 4 R 5 , benzyl, SO 3 H, or SO 3 Na, wherein R 4 and R 5 are independently H or C 1 -C 6 alkyl.
7 . The ophthalmic device of claim 1 wherein R 2 is —Y—P g .
8 . The ophthalmic device of claim 1 wherein P g at each occurrence independently comprises styryl, vinyl carbonate, vinyl ether, vinyl carbamate, N-vinyl lactam, N-vinylamide, (meth) acrylate, or (meth) acrylamide.
9 . The ophthalmic device of claim 1 wherein Y at each occurrence is independently alkylene, cycloalkylene, heterocycloalkylene, arylene, heteroarylene, oxaalkylene, alkylene-amide-alkylene, alkylene-amine-alkylene, or combinations of any of the foregoing groups.
10 . The ophthalmic device of claim 1 wherein EWG at each occurrence is independently cyano, amide, ester, keto, or aldehyde.
11 . The ophthalmic device of claim 1 wherein the compound of formula II contains one Y—P g group.
12 . The ophthalmic device of claim 1 wherein the compound of formula II is:
3-((9-(dicyanomethylene)-9H-xanthen-3-yl)oxy)propyl methacrylate;
3-((9-(dicyanomethylene)-9H-xanthen-2-yl)oxy)propyl methacrylate;
1-((9-(dicyanomethylene)-9H-xanthen-3-yl)oxy)propan-2-yl methacrylate;
4-((9-(dicyanomethylene)-9H-xanthen-3-yl)oxy)butyl methacrylate;
3-((9-(dicyanomethylene)-9H-xanthen-3-yl)oxy)propyl acrylate;
1-((9-(dicyanomethylene)-9H-xanthen-3-yl)oxy)propan-2-yl acrylate;
4-((9-(dicyanomethylene)-9H-xanthen-3-yl)oxy)butyl acrylate;
N-(3-((9-(dicyanomethylene)-9H-xanthen-3-yl)oxy)propyl) methacrylamide;
N-(3-((9-(dicyanomethylene)-9H-xanthen-3-yl)oxy)propyl) acrylamide; or
3-((9-(dicyanomethylene)-9H-xanthen-3-yl) amino) propyl methacrylate.
13 . An ophthalmic device comprising a polymeric network and a non-reactive polymer comprising repeating units derived from a compound of formula II:
wherein m and n are independently 0, 1, 2, 3, or 4;
R 1 and R 2 are independently at each occurrence H, an optional substituent, or —Y—P g , or two adjacent R 1 or R 2 groups, together with the atoms to which they are attached, combine to form a cycloalkyl or aryl ring optionally substituted with —Y—P g ;
EWG at each occurrence is independently an electron withdrawing group;
P g at each occurrence is independently a polymerizable group; and
Y at each occurrence is independently a linking group;
wherein the compound of formula II contains at least one P g group.
14 . The ophthalmic device of claim 13 wherein the non-reactive polymer further comprises repeating units derived from an amide monomer, a monofunctional polyalkylene glycol, or a combination thereof.
15 . The ophthalmic device of claim 14 wherein the amide monomer is an acyclic amide of formula H1 or H2, a cyclic amide of formula H3, or combinations thereof:
wherein R 45 is H or methyl; V is a direct bond, —(CO)—, or —(CONHR 44 )—; R 44 is C 1 to C 3 alkyl; R 40 is H or C 1 to C 4 alkyl; R 41 is H, C 1 to C 4 alkyl, amino having up to two carbon atoms, amide having up to four carbon atoms, and alkoxy having up to two carbon groups; R 42 is H, C 1 to C 4 alkyl groups; or methoxy, ethoxy, hydroxyethyl, or hydroxymethyl; R 43 is H, C 1 to C 4 alkyl; or methoxy, ethoxy, hydroxyethyl, or hydroxymethyl; wherein the number of carbon atoms in R 40 and R 41 taken together is 8 or less; and wherein the number of carbon atoms in R 42 and R 43 taken together is 8 or less; and f is a number from 1 to 10.