In one aspect, the invention relates to hydrolysis-resistant silicone compounds. In particular, disclosed are sterically hindered hydrolysis-resistant silicone compounds and improved purity hydrolysis-resistant silicone compounds. Also disclosed are processes for making hydrolysis-resistant silicone
In one aspect, the invention relates to hydrolysis-resistant silicone compounds. In particular, disclosed are sterically hindered hydrolysis-resistant silicone compounds and improved purity hydrolysis-resistant silicone compounds. Also disclosed are processes for making hydrolysis-resistant silicone compounds; the products of the disclosed processes; compositions and polymers comprising the disclosed compounds and products of the disclosed processes; and ophthalmic lenses, for example contact lenses, intraocular lenses, artificial cornea, and spectacle lenses, comprising the disclosed compositions, disclosed polymers, disclosed compounds, and products of the disclosed processes. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.
대표청구항▼
1. A compound having the structure: wherein M represents a radical-polymerizable group;wherein L has the structure: wherein G is hydrogen;wherein k is 1; andwherein m represents an integer of from 1 to 20, with the proviso that 1<3k+m<20;wherein Z1 to Z11 independently represent C1-C20 alkyl groups,
1. A compound having the structure: wherein M represents a radical-polymerizable group;wherein L has the structure: wherein G is hydrogen;wherein k is 1; andwherein m represents an integer of from 1 to 20, with the proviso that 1<3k+m<20;wherein Z1 to Z11 independently represent C1-C20 alkyl groups, with the provisos that: at least one of Z3, Z4, and Z9 is methyl, and at least one is ethyl or propyl,at least one of Z5, Z6, and Z10 is methyl, and at least one is ethyl or propyl, andat least one of Z7, Z8, and Z11 is methyl, and at least one is ethyl or propyl;wherein n represents an integer of from 0 to 200; andwherein a, b, and c independently represent integers of from 0 to 20, with the proviso that a, b, and c are not simultaneously 0. 2. The compound of claim 1, wherein M is a group comprising an acryloyloxy group or a methacryloyloxy group. 3. A compound having the structure: wherein M represents a radical-polymerizable group;wherein L has the structure: wherein G is hydrogen;wherein k is 1; andwherein m represents an integer of from 1 to 20, with the proviso that 1<3k+m<20;wherein Z1 to Z11 independently represent optionally substituted C1-C20 alkyl groups or optionally substituted C6-C20 aryl groups, with the provisos that: at least one of Z3, Z4, and Z9 is methyl, and at least one is an organic group having at least two carbon atoms,at least one of Z5, Z6, and Z10 is methyl, and at least one is an organic group having at least two carbon atoms, andat least one of Z7, Z8, and Z11 is methyl, and at least one is an organic group having at least two carbon atoms;wherein n represents an integer of from 0 to 200; andwherein a, b, and c independently represent integers of from 0 to 20, with the proviso that a, b, and c are not simultaneously 0,wherein n is 0, and wherein all of a, b, and c are 1. 4. A compound having the structure: wherein M represents a radical-polymerizable group;wherein L has the structure: wherein G is hydrogen;wherein k is 1; andwherein m represents an integer of from 1 to 20, with the proviso that 1<3k+m<20;wherein Z1 to Z11 independently represent optionally substituted C1-C20 alkyl groups or optionally substituted C6-C20 aryl groups, with the provisos that: at least one of Z3, Z4, and Z9 is methyl, and at least one is an organic group having at least two carbon atoms,at least one of Z5, Z6, and Z10 is methyl, and at least one is an organic group having at least two carbon atoms, andat least one of Z7, Z8, and Z11 is methyl, and at least one is an organic group having at least two carbon atoms;wherein n represents an integer of from 0 to 200; andwherein a, b, and c independently represent integers of from 0 to 20, with the proviso that a, b, and c are not simultaneously 0,wherein a is 0; wherein b and c are 1; and wherein Z9 comprises a methyl group, an ethyl group, a propyl group, a butyl group, or a phenyl group. 5. A compound having the structure: wherein M represents a radical-polymerizable group;wherein L has the structure: wherein G is hydrogen;wherein k is 1; andwherein m represents an integer of from 1 to 20, with the proviso that 1<3k+m<20;wherein Z1 to Z11 independently represent optionally substituted C1-C20 alkyl groups or optionally substituted C6-C20 aryl groups, with the provisos that: at least one of Z3, Z4, and Z9 is methyl, and at least one is an organic group having at least two carbon atoms,at least one of Z5, Z6, and Z10 is methyl, and at least one is an organic group having at least two carbon atoms, andat least one of Z7, Z8, and Z11 is methyl, and at least one is an organic group having at least two carbon atoms;wherein n represents an integer of from 0 to 200; andwherein a, b, and c independently represent integers of from 0 to 20, with the proviso that a, b, and c are not simultaneously 0,wherein two of Z3, Z4, and Z9 are methyl, and one of Z3, Z4, and Z9 is ethyl, propyl, or butyl;wherein two of Z5, Z6, and Z10 are methyl, and one of Z5, Z6, and Z10 is ethyl, propyl, or butyl;and wherein two of Z7, Z8, and Z11 are methyl, and one of Z5, Z6, and Z10 is ethyl, propyl, or butyl. 6. A compound having the structure: wherein M represents a radical-polymerizable group;wherein L has the structure: wherein G is hydrogen;wherein k is 1; andwherein m represents an integer of from 1 to 20, with the proviso that 1<3k+m<20;wherein Z1 to Z11 independently represent optionally substituted C1-C20 alkyl groups or optionally substituted C6-C20 aryl groups, with the provisos that: at least one of Z3, Z4, and Z9 is methyl, and at least one is an organic group having at least two carbon atoms,at least one of Z5, Z6, and Z10 is methyl, and at least one is an organic group having at least two carbon atoms, andat least one of Z7, Z8, and Z11 is methyl, and at least one is an organic group having at least two carbon atoms;wherein n represents an integer of from 0 to 200; andwherein a, b, and c independently represent integers of from 0 to 20, with the proviso that a, b, and c are not simultaneously 0,wherein Z3, Z4, Z5, Z6, Z7, and Z8 are methyl, and wherein and Z9, Z10, and Z11 are independently ethyl, propyl, or butyl. 7. The compound of claim 1, wherein the compound exhibits a hydrolysis resistance of at least about 90% at about 90° C. 8. A polymer comprising at least one residue of a compound of claim 1. 9. The polymer of claim 8, wherein at least 25% of the polymer comprises residues of a compound of claim 1. 10. The product of the process comprising the step of reacting an alkoxysilyl compound having the structure: with one or more silyl halide compounds having the structure: wherein X1, X2, and X3 independently represent a halogen selected from the group consisting of chlorine, bromine, and iodine;wherein M represents a radical-polymerizable group;wherein L represents an optionally substituted divalent C1-C20 organic group;wherein n represents an integer of from 0 to 200;wherein Q1, Q2, and Q3 independently represent hydrogen or a hydrolyzable group;wherein Z1 to Z11 independently represent C1-C20 alkyl groups, with the provisos that: at least one of Z3, Z4, and Z9 is methyl, and at least one is ethyl or propyl,at least one of Z5, Z6, and Z10 is methyl, and at least one is ethyl or propyl, andat least one of Z7, Z8, and Z11 is methyl, and at least one is ethyl or propyl;wherein a, a, b, b, c, and c independently represent integers of from 0 to 20; andwherein (a+a), (b+b), and (c+c) are, independently, integers of from 0 to 20,with the proviso that (a+a′), (b+b′), and (c+c′) are not simultaneously 0. 11. A polymer comprising at least one residue of a product of claim 10. 12. The polymer of claim 11, wherein at least 25% of the polymer comprises residues of a product of claim 10. 13. The product of the process comprising the step of reacting an alkoxysilyl compound having the structure: with one or more silyl halide compounds having the structure: wherein X1, X2, and X3 independently represent a halogen selected from the group consisting of chlorine, bromine, and iodine;wherein M represents a radical-polymerizable group;wherein L represents an optionally substituted divalent C1-C20 organic group;wherein n represents an integer of from 0 to 200;wherein Q1, Q2, and Q3 independently represent hydrogen or a hydrolyzable group;wherein Z1 to Z11 independently represent optionally substituted C1-C20 alkyl groups or optionally substituted C6-C20 aryl groups, with the provisos that: at least one of Z3, Z4, and Z9 is methyl, and at least one is an organic group having at least two carbon atoms,at least one of Z5, Z6, and Z10 is methyl, and at least one is an organic group having at least two carbon atoms, andat least one of Z7, Z8, and Z11 is methyl, and at least one is an organic group having at least two carbon atoms;wherein a, a, b, b, c, and c independently represent integers of from 0 to 20; andwherein (a+a), (b+b), and (c+c) are, independently, integers of from 1 to 20. 14. A polymer comprising at least one residue of a product of claim 13. 15. The polymer of claim 14, wherein at least 25% of the polymer comprises residues of a product of claim 13. 16. A compound having the structure: wherein M represents a radical-polymerizable group;wherein L has the structure: wherein G is hydrogen;wherein k is 1; andwherein m represents an integer of from 1 to 20, with the proviso that 1<3k+m<20;wherein Z1 to Z11 independently represent optionally substituted C1-C20 alkyl groups or optionally substituted C6-C20 aryl groups, with the provisos that: at least one of Z3, Z4, and Z9 is methyl, and at least one is an organic group having at least two carbon atoms,at least one of Z5, Z6, and Z10 is methyl, and at least one is an organic group having at least two carbon atoms, andat least one of Z7, Z8, and Z11 is methyl, and at least one is an organic group having at least two carbon atoms;wherein n represents an integer of from 0 to 200; andwherein a, b, and c independently represent integers of from 1 to 20. 17. A polymer comprising at least one residue of a compound of claim 16. 18. The polymer of claim 17, wherein at least 25% of the polymer comprises residues of a compound of claim 16. 19. The product of the process comprising the step of reacting an alkoxysilyl compound having the structure: with one or more silyl halide compounds having the structure: wherein X1, X2, and X3 independently represent a halogen selected from the group consisting of chlorine, bromine, and iodine;wherein M represents a radical-polymerizable group;wherein L represents an optionally substituted divalent C1-C20 organic group;wherein n represents an integer of from 0 to 200;wherein Q1, Q2, and Q3 independently represent hydrogen or a hydrolyzable group;wherein Z1 to Z11 independently represent optionally substituted C1-C20 alkyl groups or optionally substituted C6-C20 aryl groups, with the provisos that: at least one of Z3, Z4, and Z9 is methyl, and at least one is an organic group having at least two carbon atoms,at least one of Z5, Z6, and Z10 is methyl, and at least one is an organic group having at least two carbon atoms, andat least one of Z7, Z8, and Z11 is methyl, and at least one is an organic group having at least two carbon atoms;wherein a, a, b, b, c, and c independently represent integers of from 0 to 20; andwherein (a+a), (b+b), and (c+c) are, independently, integers of from 0 to 20,with the proviso that (a+a), (b+b), and (c+c) are not simultaneously 0,wherein n is 0, and wherein all of a, b, and c are 1. 20. The product of the process comprising the step of reacting an alkoxysilyl compound having the structure: with one or more silyl halide compounds having the structure: wherein X1, X2, and X3 independently represent a halogen selected from the group consisting of chlorine, bromine, and iodine;wherein M represents a radical-polymerizable group;wherein L represents an optionally substituted divalent C1-C20 organic group;wherein n represents an integer of from 0 to 200;wherein Q1, Q2, and Q3 independently represent hydrogen or a hydrolyzable group;wherein Z1 to Z11 independently represent optionally substituted C1-C20 alkyl groups or optionally substituted C6-C20 aryl groups, with the provisos that: at least one of Z3, Z4, and Z9 is methyl, and at least one is an organic group having at least two carbon atoms,at least one of Z5, Z6, and Z10 is methyl, and at least one is an organic group having at least two carbon atoms, andat least one of Z7, Z8, and Z11 is methyl, and at least one is an organic group having at least two carbon atoms;wherein a, a, b, b, c, and c independently represent integers of from 0 to 20; andwherein (a+a), (b+b), and (c+c) are, independently, integers of from 0 to 20,with the proviso that (a+a), (b+b), and (c+c) are not simultaneously 0,wherein a is 0; wherein b and c are 1; and wherein Z9 comprises a methyl group, an ethyl group, a propyl group, a butyl group, or a phenyl group. 21. The product of the process comprising the step of reacting an alkoxysilyl compound having the structure: with one or more silyl halide compounds having the structure: wherein X1, X2, and X3 independently represent a halogen selected from the group consisting of chlorine, bromine, and iodine;wherein M represents a radical-polymerizable group;wherein L represents an optionally substituted divalent C1-C20 organic group;wherein n represents an integer of from 0 to 200;wherein Q1, Q2, and Q3 independently represent hydrogen or a hydrolyzable group;wherein Z1 to Z11 independently represent optionally substituted C1-C20 alkyl groups or optionally substituted C6-C20 aryl groups, with the provisos that: at least one of Z3, Z4, and Z9 is methyl, and at least one is an organic group having at least two carbon atoms,at least one of Z5, Z6, and Z10 is methyl, and at least one is an organic group having at least two carbon atoms, andat least one of Z7, Z8, and Z11 is methyl, and at least one is an organic group having at least two carbon atoms;wherein a, a, b, b, c, and c independently represent integers of from 0 to 20; andwherein (a+a), (b+b), and (c+c) are, independently, integers of from 0 to 20,with the proviso that (a+a), (b+b), and (c+c) are not simultaneously 0,wherein two of Z3, Z4, and Z9 are methyl, and one of Z3, Z4, and Z9 is ethyl, propyl, or butyl;wherein two of Z5, Z6, and Z10 are methyl, and one of Z5, Z6, and Z10 is ethyl, propyl, or butyl;and wherein two of Z7, Z8, and Z11 are methyl, and one of Z5, Z6, and Z10 is ethyl, propyl, or butyl. 22. The product of the process comprising the step of reacting an alkoxysilyl compound having the structure: with one or more silyl halide compounds having the structure: wherein X1, X2, and X3 independently represent a halogen selected from the group consisting of chlorine, bromine, and iodine;wherein M represents a radical-polymerizable group;wherein L represents an optionally substituted divalent C1-C20 organic group;wherein n represents an integer of from 0 to 200;wherein Q1, Q2, and Q3 independently represent hydrogen or a hydrolyzable group;wherein Z1 to Z11 independently represent optionally substituted C1-C20 alkyl groups or optionally substituted C6-C20 aryl groups, with the provisos that: at least one of Z3, Z4, and Z9 is methyl, and at least one is an organic group having at least two carbon atoms,at least one of Z5, Z6, and Z10 is methyl, and at least one is an organic group having at least two carbon atoms, andat least one of Z7, Z8, and Z11 is methyl, and at least one is an organic group having at least two carbon atoms;wherein a, a, b, b, c, and c independently represent integers of from 0 to 20; andwherein (a+a), (b+b), and (c+c) are, independently, integers of from 0 to 20,with the proviso that (a+a), (b+b), and (c+c) are not simultaneously 0,wherein Z3, Z4, Z5, Z6, Z7, and Z8 are methyl, and wherein and Z9, Z10, and Z11 are independently ethyl, propyl, or butyl.
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