Photoactive device

Abstract

The present invention relates to novel ophthalmic devices comprising polymerizable compounds containing photoactive chromophores, specialized polymerizable compounds, and specialized monomeric compounds that are particularly suitable for compositions and ophthalmic devices. The present invention also relates to a process for altering the optical properties of said ophthalmic devices or precursor articles for ophthalmic devices.

Claims

1. An ophthalmic lens or a precursor article for an ophthalmic lens comprising an oligomer, polymer, or copolymer containing a structural unit based on at least one polymerizable compound of formula (I), 【Chemistry 1】 During the ceremony, X-W is O-C (=O), or SO ２ -O, R ３ However, it is a linear alkyl group having 1 to 8 carbon atoms, R ４ However, it is F, Cl, CN, a linear alkyl group having 1 to 8 carbon atoms, or a fully fluorinated alkyl group having 1 to 8 carbon atoms. R ５ However, in each instance, independently, it is Cl, a linear alkyl group having 1 to 8 carbon atoms, or a linear alkoxy group having 1 to 8 carbon atoms. x is 0 or 1, Y is O, R １ However, it is a polymerizable group of formula (4), 【Chemistry 2】 During the ceremony, X １１ However, C(=O)O, R ６ 、 R ７ 、 R ８ are, in each occurrence, independently of one another, H or a straight-chain, non-fluorinated alkyl group having 1 to 20 carbon atoms c is 1, -R ２ - but - (CH ２ ) ｏ - or - (CH ２ ) ｐ -O ８ - (CH ２ ) ｑ -O ｓ - (CH ２ ) ｒ -O ｔ - (CH ２ ) ｕ - and o is selected from a group consisting of 5 to 20, s and t are 0 or 1, p and q are independently selected in each existence from a group consisting of 1 to 10. r and u are independently selected in each existence from the group consisting of 0 to 10, in the formula - (CH ２ ) ｐ -O-(CH ２ ) ｑ -O ｓ - (CH ２ ) ｒ - (O) ｔ - (CH) ｕ An ophthalmic lens, or a precursor article for an ophthalmic lens, wherein the total number of atoms of the negative compound is at most 20.

2. The oligomer, polymer, or copolymer comprises a constituent unit based on at least one polymerizable compound of formula (Ia), (Ib), or (Ic), 【Transformation 3】 In the formula, R １ , -R ２ -, Y, R ３ , R ４ , X-W, x and R ５ The ophthalmic lens or precursor article for an ophthalmic lens according to claim 1, having the meaning described in claim 1.

3. An ophthalmic lens or a precursor article for an ophthalmic lens according to claim 1 or 2, wherein X-W is O-C (=O).

4. Constituent unit M based on formulas (I), (Ia), (Ib), or (Ic) ０ The formula includes an oligomer, polymer, or copolymer containing R １ In each existence, they are polymerized, and therefore, R １ An ophthalmic lens or precursor article for an ophthalmic lens according to any one of claims 1 to 3, wherein the ophthalmic lens forms a regioregular, alternating, regiorandom, statistical, block, or random oligomer or polymer main chain, or is part of the main chain of the copolymer.

5. Polymerized group R １ However, this is the one in equation (4-p), 【Chemistry 4】 asterisk" ＊ " indicates a bond to an adjacent repeating unit in the polymer chain or oligomer chain, or to a terminal group, and an asterisk " ＊＊ An ophthalmic lens or precursor article for an ophthalmic lens according to any one of claims 1 to 4, wherein " indicates bonding to the remainder of formula (I), (Ia), (Ib), or (Ic).

6. The aforementioned structural unit M ０ However, formula (M ０ -I), (M ０ -Ia), (M ０ -Ib) or (M ０ -Ic) is, 【Transformation 5】 In the formula, R １ , -R ２ -, X-W, Y, R ３ , R ４ , R ５ , x, R ６ , R ７ , R ８ , X １１ and c have the meanings described in claim 1, and in the formula, the asterisk " ＊ The ophthalmic lens or precursor article for an ophthalmic lens according to claim 4, wherein in each presence, the '' exhibits bonding to the adjacent repeating units in the polymer chain or oligomer chain, or to the terminal groups.

7. The oligomer, polymer, or copolymer is the constituent unit based on at least one polymerizable compound of formula (I), (Ia), (Ib), or (Ic), or formula (M ０ -I), (M ０ -Ia), (M ０ -Ib), (M ０ -Ic) The aforementioned constituent unit M ０ In addition, styrene, ethoxyethyl methacrylate (EOEMA), methyl methacrylate (MMA), methyl acrylate, n-alkyl acrylate (n-alkyl group containing 2 to 20 carbon atoms), n-alkyl methacrylate (n-alkyl group containing 2 to 20 carbon atoms), i-alkyl acrylate (i-alkyl group containing 3 to 20 carbon atoms), i-alkyl methacrylate (i-alkyl group containing 3 to 20 carbon atoms), ethoxyethoxyethyl acrylate (EEEA), n-hydroxyalkyl acrylate (2 to 10 carbon atoms) n-alkyl groups (containing n-alkyl groups), n-hydroxyalkyl methacrylate (n-alkyl groups containing 2 to 10 carbon atoms), tetrahydrofuryl methacrylate (THFMA), glycidyl methacrylate (GMA), 16-hydroxyhexadecyl acrylate, 16-hydroxyhexadecyl methacrylate, 18-hydroxyoctadecyl acrylate, 18-hydroxyoctadecyl methacrylate, 2-phenoxyethyl acrylate (EGPEA), heptafluorobutyl acrylate, heptafluorobutyl methacrylate, hexafluorobutyl Acrylate, hexafluorobutyl methacrylate, hexafluoroisopropyl acrylate, hexafluoroisopropyl methacrylate, octafluoropentyl acrylate, octafluoropentyl methacrylate, betanfluoropropyl acrylate, pentafluoropropyl methacrylate, tetrafluoropropyl methacrylate, trifluoroethyl acrylate, trifluoroethyl methacrylate, trimethylcyclohexyl acrylate, trimethylcyclohexyl methacrylate, 2-(4-bromophenyl)ethyl methacrylate, 4-phenylbutyl methacrylate, 4-methylphenyl methacrylate, phenyl methacrylate, 4-methylphenyl acrylate, benzyl acrylate, benzyl methacrylate, 2-benzyloxyethyl methacrylate, 3-benzyloxypropyl methacrylate, phenylethyl acrylate, 3-phenylpropyl methacrylate, 2-phenoxyethyl acrylate, 2-benzyloxyethyl acrylate, 3-phenylpropyl acrylate, 4-methylbenzyl acrylate,Phenyl acrylate, 2-(phenylthio)ethyl methacrylate, 4-phenylbutyl acrylate, 5-phenylpentyl acrylate, 3-benzyloxypropyl acrylate, 2-(phenylthio)propyl acrylate, 2-(phenylthio)ethyl acrylate, 4-phenylbutyl acrylate, 4-methylbenzyl methacrylate, 2-(2-methylphenyl)ethyl acrylate, 2-(2-methylphenyl)ethyl methacrylate, 2-(3-methylphenyl)ethyl acrylate, 2-(3-methylphenyl)ethyl methacrylate 4-methylphenyl)ethyl acrylate, 2-(4-methylphenyl)ethyl methacrylate, 2-(4-propylphenyl)ethyl acrylate, 2-(4-propylphenyl)ethyl methacrylate, 2-(4-(1-methylethyl)phenyl)ethyl acrylate, 2-(4-(1-methylethyl)phenyl)ethyl methacrylate, 2-(4-methoxyphenyl)ethyl methacrylate, 2-(4-methoxyphenyl))ethyl acrylate, 2-(4-cyclohexylphenyl)ethyl acrylate, 2-(4 -Cyclohexylphenyl) ethyl methacrylate, 2-(4-chlorophenyl) ethyl methacrylate, 2-(4-chlorophenyl) ethyl acrylate, 2-(3-chlorophenyl) ethyl methacrylate, 2-(3-chlorophenyl) ethyl acrylate, 2-(2-chlorophenyl) ethyl methacrylate, 2-(2-chlorophenyl) ethyl acrylate, 2-(4-bromophenyl) ethyl acrylate, 2-(4-phenylphenyl) ethyl methacrylate, 2-(4-phenylphenyl) ethyl acrylate, 2-(3-phenyl Phenyl)ethyl methacrylate, 2-(3-phenylphenyl)ethyl acrylate, 2-(4-benzylphenyl)ethyl methacrylate, 2-(4-benzylphenyl)ethyl acrylate, 2-(phenylthio)ethyl acrylate, 3-benzyloxypropyl acrylate, 2-[2-(benzyloxy)ethoxy]ethyl acrylate, 2-[2-(benzyloxy)ethoxy]ethyl methacrylate, pentafluorophenyl methacrylate, heptadecafluorodecyl methacrylate, dodecafluoroheptyl methacrylate,An ophthalmic lens or precursor article for an ophthalmic lens according to any one of claims 1 to 6, comprising a constituent unit based on heptadecafluorodecyl acrylate or pentafluorophenyl acrylate.

8. The ophthalmic lens or precursor article for an ophthalmic lens according to claim 7, wherein the at least one further polymerizable comonomer is selected from methyl methacrylate, alkyl n-acrylate (n-alkyl group containing 2 to 20 carbon atoms), fluorinated alkyl n-acrylate (n-alkyl group containing 2 to 20 carbon atoms), n-alkyl methacrylate (n-alkyl group containing 2 to 20 carbon atoms), fluorinated n-alkyl methacrylate (n-alkyl group containing 2 to 20 carbon atoms), alkyl i-acrylate (i-alkyl group containing 3 to 20 carbon atoms), fluorinated alkyl i-acrylate (i-alkyl group containing 3 to 20 carbon atoms), i-alkyl methacrylate (i-alkyl group containing 3 to 20 carbon atoms), fluorinated i-alkyl methacrylate, n-hydroxyalkyl acrylate (n-alkyl group containing 2 to 10 carbon atoms), n-hydroxyalkyl methacrylate (n-alkyl group containing 2 to 10 carbon atoms), or a mixture thereof.

9. -R ２ - In each existence independently, - (CH ２ ) ｏ - An ophthalmic lens or a precursor article for an ophthalmic lens according to any one of claims 1 to 8.

10. Polymerizable R １ An ophthalmic lens or precursor article for an ophthalmic lens according to any one of claims 1 to 9, wherein each is independently derived from an acryloyloxy group or a methacryloyloxy group.

11. The precursor article for an ophthalmic lens according to any one of claims 1 to 10, wherein the precursor article is a blank that can be transformed into an ophthalmic implant, preferably an intraocular lens.

12. A process for forming an ophthalmic lens or a precursor article for an ophthalmic lens according to any one of claims 1 to 11, wherein the process comprises: - A step of providing a composition comprising: an oligomer or polymer having at least one compound of formula (I), (Ia), (Ib), or (Ic) as described in any one of claims 1 to 3, 9, and 10, and / or at least one compound of formula (I), (Ia), (Ib), or (Ic) as described in any one of claims 1 to 3, 9, and 10, and at least one reactive group remaining for polymerization, and further monomers optionally different from the compound of formula (I), (Ia), (Ib), or (Ic), and / or a crosslinking agent, and / or an ultraviolet absorber, and / or a radical initiator; A process comprising the steps of subsequently forming the ophthalmic lens or the precursor article of the ophthalmic lens.

13. A process for changing the optical properties of an ophthalmic lens or a precursor article for an ophthalmic lens according to any one of claims 1 to 11, wherein the process comprises: - A step of providing an ophthalmic lens or precursor article as described in claim 1, - A process comprising the step of exposing the ophthalmic lens or the precursor article to irradiation having a wavelength of at least 200 nm and a maximum of 1500 nm.

14. A compound of formula (I), 【Transformation 6】 During the ceremony, X-W is O-C (=O), or SO ２ -O, R ３ However, it is a linear alkyl group having 1 to 8 carbon atoms, R ４ However, it is F, Cl, a linear alkyl group having 1 to 8 carbon atoms, or a fully fluorinated alkyl group having 1 to 8 carbon atoms. R ５ However, in each instance, independently, it is Cl, a linear alkyl group having 1 to 8 carbon atoms, or a linear alkoxy group having 1 to 8 carbon atoms. x is 0 or 1, Y is O, R １ However, it is a polymerizable group of formula (4), 【Transformation 7】 During the ceremony, X １１ However, C(=O)O, R ６ , R ７ , R ８ However, in each instance, they are linear, non-fluorinated alkyl groups having 1 to 20 H or carbon atoms, independently of each other. c is 1, -R ２ - but - (CH ２ ) ｏ - and A compound in which o is selected from the group consisting of 5 to 20.

15. An oligomer, polymer, or copolymer comprising a structural unit based on at least one polymerizable compound of formula (I) as described in claim 14.

16. In addition to the constituent units based on the polymerizable compound of formula (I), styrene, ethoxyethyl methacrylate (EOEMA), methyl methacrylate (MMA), methyl acrylate, n-alkyl acrylate (n-alkyl group containing 2 to 20 carbon atoms), n-alkyl methacrylate (n-alkyl group containing 2 to 20 carbon atoms), i-alkyl acrylate (i-alkyl group containing 3 to 20 carbon atoms), i-alkyl methacrylate (i-alkyl group containing 3 to 20 carbon atoms), ethoxyethoxyethyl acrylate (EEEA), n-hydroxyal Kill acrylate (n-alkyl group containing 2 to 10 carbon atoms), n-hydroxyalkyl methacrylate (n-alkyl group containing 2 to 10 carbon atoms), tetrahydrofuryl methacrylate (THFMA), glycidyl methacrylate (GMA), 16-hydroxyhexadecyl acrylate, 16-hydroxyhexadecyl methacrylate, 18-hydroxyoctadecyl acrylate, 18-hydroxyoctadecyl methacrylate, 2-phenoxyethyl acrylate (EGPEA), heptafluorobutyl acrylate, heptafluorobutyl 1-Methacrylate, hexafluorobutyl acrylate, hexafluorobutyl methacrylate, hexafluoroisopropyl acrylate, hexafluoroisopropyl methacrylate, octafluoropentyl acrylate, octafluoropentyl methacrylate, betanfluoropropyl acrylate, pentafluoropropyl methacrylate, tetrafluoropropyl methacrylate, trifluoroethyl acrylate, trifluoroethyl methacrylate, trimethylcyclohexyl acrylate, trimethylcyclohexyl methacrylate, 2-(4-bromophenyl)ethyl methacrylate, 4-phenylbutyl methacrylate, 4-methylphenyl methacrylate, phenyl methacrylate, 4-methylphenyl acrylate, benzyl acrylate, benzyl methacrylate, 2-benzyloxyethyl methacrylate, 3-benzyloxypropyl methacrylate, phenylethyl acrylate, 3-phenylpropyl methacrylate, 2-phenoxyethyl acrylate, 2-benzyloxyethyl acrylate, 3-phenylpropyl acrylate,4-methylbenzyl acrylate, phenyl acrylate, 2-(phenylthio)ethyl methacrylate, 4-phenylbutyl acrylate, 5-phenylpentyl acrylate, 3-benzyloxypropyl acrylate, 2-(phenylthio)propyl acrylate, 2-(phenylthio)ethyl acrylate, 4-phenylbutyl acrylate, 4-methylbenzyl methacrylate, 2-(2-methylphenyl)ethyl acrylate, 2-(2-methylphenyl)ethyl methacrylate, 2-(3-methylphenyl)ethyl acrylate, 2-(3 2-(methylphenyl)ethyl methacrylate, 2-(4-methylphenyl)ethyl acrylate, 2-(4-methylphenyl)ethyl methacrylate, 2-(4-propylphenyl)ethyl acrylate, 2-(4-propylphenyl)ethyl methacrylate, 2-(4-(1-methylethyl)phenyl)ethyl acrylate, 2-(4-(1-methylethyl)phenyl)ethyl methacrylate, 2-(4-methoxyphenyl)ethyl methacrylate, 2-(4-methoxyphenyl))ethyl acrylate, 2-(4-cyclohexylphenyl)ethyl acrylate 2-(4-cyclohexylphenyl)ethyl methacrylate, 2-(4-chlorophenyl)ethyl methacrylate, 2-(4-chlorophenyl)ethyl acrylate, 2-(3-chlorophenyl)ethyl methacrylate, 2-(3-chlorophenyl)ethyl acrylate, 2-(2-chlorophenyl)ethyl methacrylate, 2-(2-chlorophenyl)ethyl acrylate, 2-(4-bromophenyl)ethyl acrylate, 2-(4-phenylphenyl)ethyl methacrylate, 2-(4-phenylphenyl)ethyl acrylate, 2-(3- Phenylephenyl) ethyl methacrylate, 2-(3-phenylphenyl) ethyl acrylate, 2-(4-benzylphenyl) ethyl methacrylate, 2-(4-benzylphenyl) ethyl acrylate, 2-(phenylthio) ethyl acrylate, 3-benzyloxypropyl acrylate, 2-[2-(benzyloxy)ethoxy]ethyl acrylate, 2-[2-(benzyloxy)ethoxy]ethyl methacrylate, pentafluorophenyl methacrylate, heptadecafluorodecyl methacrylate, dodecafluoroheptyl methacrylate,The polymer according to claim 15, comprising a structural unit based on at least one further polymerizable monomer selected from the group consisting of heptadecafluorodecyl acrylate and pentafluorophenyl acrylate.

17. A composition comprising at least one compound of formula (I) as described in claim 14, and / or an oligomer or polymer as described in claim 15 or 16 having at least one reactive group remaining for polymerization.

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