Silicone hydrogel lens with a crosslinked hyrdophilic coating
US-2017038501-A1 · Feb 9, 2017 · US
US9748576B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9748576-B2 |
| Application number | US-201514589172-A |
| Country | US |
| Kind code | B2 |
| Filing date | Jan 5, 2015 |
| Priority date | Aug 12, 2014 |
| Publication date | Aug 29, 2017 |
| Grant date | Aug 29, 2017 |
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A polymer including a first repeating unit including at least one carboxyl group substituted with a cation and a second repeating unit including at least one carboxyl group substituted with a moiety containing a dihydroxyphenyl group.
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What is claimed is: 1. A polymer comprising: a first repeating unit comprising at least one carboxyl group substituted with a cation, wherein the cation comprises at least one selected from Li + , Na + , K + , and NH 4 + ; and a second repeating unit comprising at least one carboxyl group substituted with a moiety comprising a dihydroxyphenyl group, wherein the first repeating unit is represented by Formula 1 and the second repeating unit is represented by Formula 2: wherein in Formula 1, L is selected from a single bond, a substituted or unsubstituted C 1 -C 6 alkylene group, a substituted or unsubstituted C 1 -C 6 heteroalkylene group, a substituted or unsubstituted C 2 -C 6 alkenylene group, a substituted or unsubstituted C 2 -C 6 alkynylene group, a substituted or unsubstituted C 6 -C 10 arylene group, and a substituted or unsubstituted C 6 -C 10 heteroarylene group; R 1 and R 2 are each independently selected from a hydrogen, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 7 -C 30 arylalkyl group, a substituted or unsubstituted C 7 -C 30 arylalkoxy group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 2 -C 30 heteroaryloxy group, a substituted or unsubstituted C 3 -C 30 heteroarylalkyl group, a substituted or unsubstituted C 3 -C 30 heteroarylalkoxy group, a substituted or unsubstituted C 4 -C 30 carbocyclic group, a substituted or unsubstituted C 4 -C 30 carbocyclic oxy group, a substituted or unsubstituted C 5 -C 30 carbocyclic alkyl group, a substituted or unsubstituted C 5 -C 30 carbocyclic alkoxy group, a substituted or unsubstituted C 2 -C 30 heterocyclic group, a substituted or unsubstituted C 2 -C 30 heterocyclic oxy group, a substituted or unsubstituted C 2 -C 30 heterocyclic alkyl group, and a substituted or unsubstituted C 2 -C 30 heterocyclic alkoxy group; and R 5 and R 6 are each independently selected from a hydrogen, —C(═O)OH, and —C(═O)O-M, wherein M is selected from Li + , Na + , K + , and NH 4 + , at least one of R 5 and R 6 is —C(═O)O-M; and wherein in Formula 2, L 1 is selected from a single bond, a substituted or unsubstituted C 1 -C 6 alkylene group, a substituted or unsubstituted C 1 -C 6 heteroalkylene group, a substituted or unsubstituted C 2 -C 6 alkenylene group, a substituted or unsubstituted C 2 -C 6 alkynylene group, a substituted or unsubstituted C 6 -C 10 arylene group, and a substituted or unsubstituted C 6 -C 10 heteroarylene group; R 3 and R 4 are each independently selected from a hydrogen, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 7 -C 30 arylalkyl group, a substituted or unsubstituted C 7 -C 30 arylalkoxy group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 2 -C 30 heteroaryloxy group, a substituted or unsubstituted C 3 -C 30 heteroarylalkyl group, a substituted or unsubstituted C 3 -C 30 heteroarylalkoxy group, a substituted or unsubstituted C 4 -C 30 carbocyclic group, a substituted or unsubstituted C 4 -C 30 carbocyclic oxy group, a substituted or unsubstituted C 5 -C 30 carbocyclic alkyl group, a substituted or unsubstituted C 5 -C 30 carbocyclic alkoxy group, a substituted or unsubstituted C 2 -C 30 heterocyclic group, a substituted or unsubstituted C 2 -C 30 heterocyclic oxy group, a substituted or unsubstituted C 2 -C 30 heterocyclic alkyl group, and a substituted or unsubstituted C 2 -C 30 heterocyclic alkoxy group; and R 7 and R 8 are each independently selected from a hydrogen, —C(═O)OH, an amide group substituted with R a , and an ammonium carboxylate salt substituted with R a , wherein R a is a 3,4-dihydroxyphenyl group linked to an unsubstituted C 1 -C 5 alkylene group, provided that at least one of R 7 and R 8 is at least one selected from an amide group substituted with R a and an ammonium carboxylate salt substituted with R a . 2. The polymer of claim 1 , wherein the moiety comprising a dihydroxyphenyl group comprises at least one selected from a moiety comprising a 3,4-dihydroxyphenyl group linked to a C 1 -C 5 alkylene group substituted with a hydroxyl group, a moiety comprising a 3,4-dihydroxyphenyl group linked to an unsubstituted C 1 -C 5 alkylene group, a 3,4-dihydroxyphenyl group linked to a C 1 -C 5 heteroalkylene group substituted with a hydroxyl group, and a moiety comprising a 3,4-dihydroxyphenyl group linked to an unsubstituted C 1 -C 5 heteroalkylene group. 3. The polymer of claim 1 , wherein the moiety comprising a dihydroxyphenyl group comprises at least one selected from 2-(3,4-dihydroxyphenyl)ethyl-1-amine, 2-hydroxy-2-(3,4-dihydroxyphenyl)ethyl-1-amine, and 2-hydroxy-2-(3,4-dihydroxyphenyl)ethyl-1-methylamine. 4. The polymer of claim 1 , wherein the polymer has a weight average molecular weight in a range of about 100,000 Daltons to about 3,000,000 Daltons. 5. The polymer of claim 1 , wherein the polymer further comprises a third repeating unit represented by Formula 3 and a fourth repeating unit represented by Formula 4: wherein in Formula 3, R 9 and R 10 are each independently selected from a hydrogen and a substituted or unsubstituted C 1 -C 10 alkyl group, wherein in Formula 4, L 3 is selected from a single bond, a substituted or unsubstituted C 1 -C 10 alkylene group, a substituted or unsubstituted C 1 -C 10 heteroalkylene group, a substituted or unsubstituted C 2 -C 10 alkenylene group, a substituted or unsubstituted C 2 -C 10 alkynylene group, a substituted or unsubstituted C 6 -C 10 arylene group, a substituted or unsubstituted C 6 -C 10 heteroarylene group; and R 11 to R 14 are each independently selected from a hydrogen, —C(═O)OH, a substituted or unsubstituted C 1 -C 10 alkyl group, and a substituted or unsubstituted C 1 -C 10 alkoxy group. 6. The polymer of claim 5 , wherein the polymer has a weight average molecular weight in a range of about 100,000 Daltons to about 3,000,000 Daltons. 7. The polymer of claim 1 , wherein the polymer comprises at least one of polymers represented by Formulae 5 to 8, and has a weight average molecular weight in a range of about 100,000 Daltons to about 3,000,000 Daltons: wherein in Formula 5, x and y each indicate a mole fraction, and 0<x <1, 0<y <1, provided that x+y =1; M 1 is at least one selected from Li + , Na + , K + , and NH 4 + ; and Q is at least one selected from an amide group substituted with R b and an ammonium carboxylate salt substituted with R b , wherein R b is a 3,4-dihydroxyphenyl group link
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