High refractive index aromatic-based prepolymers
View Patent ↗Relatively high refractive index polymeric compositions and ophthalmic devices such as for example intraocular lenses and corneal inlays made therefrom are described herein. The preferred polymeric compositions are produced through the copolymerization of one or more aromatic-substituted polysiloxane prepolymers with one or more aromatic monomers, alkylated monomers or hydrophilic monomers.
1. A polymeric composition produced through the copolymerization of one or more prepolymers
wherein the V groups may be the same or different unsaturated photo or thermal polymerizable substituents of the general structure
R 3 CH═C(R 4 )(CH 2 ) p (W) q (Z) q (Ar) q R 5 ; the R groups may be the same or different saturated C 1-10 hydrocarbon substituents; the R 1 groups may be the same or different C 1-10 alkyl substituents; the R 2 groups may be the same or different selected from the group consisting of C 1-10 alkyl substituents, C 1-10 fluoroalkyl substituents, C 2-20 alkyl-fluoroalkyl substituents and C 6-30 aromatic substituents;
the L groups, which may or may not be present in the subject prepolymers, may be the same or different urethane, urea or ester linkages; y is a natural number greater than 4 representing the sum of siloxane moieties with randomly differing R 2 groups as defined above so as to have a molar ratio of aromatic substituents to alkyl substituents no less than 1:4; x is a natural number such that the prepolymer molecular weight is at least approximately 1000 and refractive index is at least approximately 1.45; R 3 is selected from the group consisting of hydrogen, C 1-10 alkyl and —CO—U; R 4 is selected from the group consisting of hydrogen and methyl; R 5 is a C 1-10 divalent alkylene radical; the W group is selected from the group consisting of —O— and —OCO—; the Z group is selected from the group consisting of —O— and —NH—; the Ar groups may be the same or different C 6-30 aromatic radicals: p is a non-negative integer less than 7; q is either 0 or 1; and U is selected from the group consisting of —OC 1-12 alkyl radical, —SC 1-12 alkyl radical and —NHC 1-12 alkyl radical; with one or more aromatic monomers, alkyl monomers, hydrophilic monomers or a combination thereof.
2. The polymeric composition of claim 1 wherein said one or more aromatic monomers are selected from the group consisting of acrylates, methacrylates, acrylamides and methacrylamides, each with aromatic substituents.
3. The polymeric composition of claim 1 wherein said one or more aromatic monomers are selected from the group consisting of phenyl acrylate, phenyl(meth)acrylate, phenyl acrylamide, benzyl acrylate, benzyl acrylamide, phenylethylacrylate, phenyl(meth)acrylamide, phenylethyl(meth)acrylate and benzyl(meth)acrylate.
4. The polymeric composition of claim 1 wherein said one or more alkyl monomers are selected from the group consisting of C 1-20 alkyl acrylate, C 1-20 alkyl methacrylate, C 5-20 acrylamide and C 5-20 methacrylamide.
5. The polymeric composition of claim 1 wherein said one or more alkyl monomers are selected from the group consisting of methyl acrylate, ethyl acrylate, n-propyl acrylate, n-butyl acrylate, n-hexyl acrylate, n-octyl acrylate, 2-ethylhexyl acrylate, n-propyl methacrylate, n-butyl methacrylate, n-hexyl methacrylate, n-octyl methacrylate, 2-ethylhexyl methacrylate and n-octyl acrylamide.
6. The polymeric composition of claim 1 wherein said one or more hydrophilic monomers are selected from the group consisting of N,N-dimethyl acrylamide, N-vinylpyrrolidone, 2-hydroxyethyl methacrylate, glycerol methacrylate, 2-hydroxyethyl acrylate, acrylamide, n-methyl acrylamide, acrylic acid and (meth)acrylic acid.
7. A method of producing the polymeric composition of claim 1 useful in the manufacture of ophthalmic devices comprising:
reacting one or more polysiloxane prepolymers with one or more aromatic monomers, alkyl monomers or hydrophilic monomers.
8. The method of claim 7 wherein said one or more aromatic monomers are selected from the group consisting of acrylates, methacrylates, acrylamides and methacrylamides, each with aromatic substituents.
9. The method of claim 7 wherein said one or more aromatic monomers are selected from the group consisting of phenyl acrylate, phenyl(meth)acrylate, phenyl acrylamide, benzyl acrylate, benzyl acrylamide, phenylethylacrylate, phenyl(meth)acrylamide, phenylethyl(meth)acrylate and benzyl(meth)acrylate.
10. The method of claim 7 wherein said one or more alkyl monomers are selected from the group consisting of C 1-20 alkyl acrylate, C 1-20 alkyl methacrylate, C 5-20 acrylamide and C 5-20 methacrylamide.
11. The method of claim 7 wherein said one or more alkyl monomers are selected from the group consisting of methyl acrylate, ethyl acrylate, n-propyl acrylate, n-butyl acrylate, n-hexyl acrylate, n-octyl acrylate, 2-ethylhexyl acrylate, n-propyl methacrylate, n-butyl methacrylate, n-hexyl methacrylate, n-octyl methacrylate, 2-ethylhexyl methacrylate and n-octyl acrylamide.
12. The method of claim 7 wherein said one or more hydrophilic monomers are selected from the group consisting of N,N-dimethyl acrylamide, N-vinylpyrrolidone, 2-hydroxyethyl methacrylate, glycerol methacrylate, 2-hydroxyethyl acrylate, acrylamide, n-methyl acrylamide, acrylic acid and (meth)acrylic acid.