Claims
- 1. A method comprising the steps of
(a) curing a reactive monomer mix comprising at least one lens forming component and at least one ligand monomer under conditions sufficient to provide a reactivity ratio of the ligand monomer to at least one major lens forming component of at least about 0.45 lens; and (b) treating said lens with a silver solution to form an antimicrobial lens comprising silver in an amount which is at least about 80% of target silver concentration, where the ligand monomer is of Formulae 1, 11, III or IV, 6wherein R1 is hydrogen or C1-6alkyl; R is —OR3, —NH—R3, —S—(CH2)d—R3,or —(CH2)d—R3, wherein d is 0-8; R3 is substituted C1-6alkyl where the alkyl substituents are selected from one or more members of the group consisting of carboxylic acid, sulfonic acid, phosphonic acid, amine, amidine, acetamide, nitrile, thiol, C1-6alkyldisulfide, C1-6alkylsulfide, phenyldisulfide, urea, C1-6alkylurea, phenylurea, thiourea, C1-6alkylthiourea, phenylthiourea, substituted C1-6alkyldisulfide, substituted phenyldisulfide, substituted C1-6alkylurea, substituted phenylurea, substituted C1-6alkylthiourea, and substituted phenylthiourea wherein the C1-6alkyldisulfide, phenyldisulfide, C1-6alkylurea, C1-6alkylthiourea, phenylurea, and phenylthiourea substituents are selected from the group consisting of C1-6alkyl, haloC1-6alkyl, halogen, hydroxyl, carboxylic acid, sulfonic acid, phosphonic acid, amine, amidine, acetamide, and nitrile; —(CR4R5)q—(CHR6)m—SO3H wherein R4, R5, and R6 are independently selected from the group consisting of hydrogen, halogen, hydroxyl, and C1-6alkyl, q is 1-6, and m is 0-6; —(CH2)n—S—S—(CH2)xNH—C(O)CR7CH2, wherein R7 is hydrogen or C1-6alkyl, n is 1-6, and x is 1-6; —(CR8R9)t—(CHR10)u—P(O)(OH)2 wherein R8, R9, and R10 are independently selected from the group consisting of hydrogen, halogen, hydroxyl, and C1-6alkyl, t is 1-6, and u is 0-6; phenyl, benzyl, pyridinyl, pyrimidinyl, pyrazinyl, benzimidazolyl, benzothiazolyl, benzotriazolyl, naphthaloyl, quinolinyl, indolyl, thiadiazolyl, triazolyl, 4-methylpiperidin-1-yl, 4-methylpiperazin-1-yl, substituted phenyl, substituted benzyl, substituted pyridinyl, substituted pyrimidinyl, substituted pyrazinyl, substituted benzimidazolyl, substituted benzothiazolyl, substituted benzotriazolyl, substituted naphthaloyl, substituted quinolinyl, substituted indolyl, substituted thiadiazolyl, substituted triazolyl, substituted 4-methylpiperidin-1-yl; or substituted 4-methylpiperazin-1-yl, wherein the substituents are selected from one or more members of the group consisting of C1-6alkyl, haloC1-6alkyl, halogen, sulfonic acid, phosphonic acid, hydroxyl, carboxylic acid, amine, amidine, N-(2-aminopyrimidine)sulfonyl, N-(aminopyridine)sulfonyl, N-(aminopyrazine)sulfonyl, N-(2-aminopyrimidine)carbonyl, N-(aminopyridine)carbonyl, N-(aminopyrazine)carbonyl, N-(2-aminopyrimidine)phosphonyl, N-(2-aminopyridine)phosphonyl, N-(aminopyrazine)phosphonyl, N-(aminobenzimidazolyl)sulfonyl, N-(aminobenzothiazolyl)sulfonyl, N-(aminobenzotriazolyl)sulfonyl, N-(aminoindolyl)sulfonyl, N-(aminothiazolyl)sulfonyl, N-(aminotriazolyl)sulfonyl, N-(amino-4-methylpiperidinyl)sulfonyl, N-(amino-4-methylpiperazinyl)sulfonyl, N-(aminobenzimidazolyl)carbonyl, N-(aminobenzothiazolyl)carbonyl, N-(aminobenzotriazolyl)carbonyl, N-(aminoindolyl)carbonyl, N-(aminothiazolyl)carbonyl, N-(aminotriazolyl)carbonyl, N-(amino-4-methylpiperidinyl)carbonyl, N-(amino-4-methylpiperazinyl)carbonyl, N-(2-aminobenzimidazolyl)phosphonyl, N-(2-aminobenzothiazolyl)phosphonyl, N-(2-aminobenzotriazolyl)phosphonyl, N-(2-aminoindolyl)phosphonyl, N-(2-aminothiazolyl)phosphonyl, N-(2-aminotriazolyl)phosphonyl, N-(amino-4-methylpiperidinyl) phosphonyl, N-(amino-4-methylpiperazinyl) phosphonyl, acetamide, nitrile, thiol, C1-6alkyldisulfide, C1-6alkylsulfide, phenyl disulfide, urea, C1-6alkylurea, phenylurea, thiourea, C1-6alkylthiourea, phenylthiourea, substituted C1-6alkyldisulfide, substituted phenyldisulfide, substituted C1-6alkylurea, substituted C1-6alkylthiourea, substituted phenylurea, and substituted phenylthiourea wherein the C1-6alkyldisulfide, phenyldisulfide, C1-6alkylurea, C1-6alkylthiourea, phenylurea, and phenylthiourea substituents are selected from the group consisting of C1-6alkyl, haloC1-6alkyl, halogen, hydroxyl, carboxylic acid, sulfonic acid, phosphonic acid, amine, amidine, acetamide, and nitrite; a is 1-5; R11 is hydrogen or C1-6alkyl; R12 is hydroxyl, sulfonic acid, phosphonic acid, carboxylic acid, acetamide, thioC1-6alkylcarbonyl, C1-6alkyldisulfide, C1-6alkylsulfide, phenyl disulfide, urea, C1-6alkylurea, phenylurea, thiourea, C1-6alkylthiourea, phenylthiourea, —OR13, —NH—R13, —S—(CH2)d—R13, —(CH2)d—R13, —C(O)NH—(CH2)d—R13, —C(O)—(CH2)d—R13, substituted C1-6alkyldisulfide, substituted phenyldisulfide, substituted C1-6alkylurea, substituted phenylurea, substituted phenylthiourea or substituted C1-6alkylthiourea wherein the substituents are selected from the group consisting of C1-6alkyl, haloC1-6alkyl, halogen, hydroxyl, carboxylic acid, sulfonic acid, phosphonic acid, amine, amidine, acetamide, and nitrile; where d is 0-8; R13 is thioC1-6alkylcarbonyl; substituted C1-6alkyl where the alkyl substituents are selected from one or more members of the group consisting of hydroxyl, carboxylic acid, sulfonic acid, phosphonic acid, amine, amidine, acetamide, nitrile, thiol, C1-6alkyldisulfide, C1-6alkylsulfide, phenyldisulfide, urea, C1-6alkylurea, phenylurea, thiourea, C1-6alkylthiourea, phenylthiourea, substituted C1-6alkyldisulfide, substituted phenyldisulfide, substituted C1-6alkylurea, substituted phenylurea, substituted C1-6alkylthiourea and substituted phenylthiourea wherein the C1-6alkyldisulfide, phenyldisulfide, C1-6alkylurea, C1-6alkylthiourea, phenylurea, and phenylthiourea substituents are selected from the group consisting of C1-6alkyl, haloC1-6alkyl, halogen, hydroxyl, carboxylic acid, sulfonic acid, phosphonic acid, amine, amidine, acetamide, and nitrile; —(CR14R15)q—(CHR16)m—SO3H where R14, R15, and R16 are independently selected from the group consisting of hydrogen, halogen, hydroxyl, and C1-6alkyl, q is 1-6, and m is 0-6; —(CH2)n—S—S—(CH2)xNH—C(O)CR17CH2, where R17 is hydrogen or C1-6alkyl, n is 1-6, and x is 1-6; —(CR18 R19)t—(CHR20)u—P(O)(OH)2 where R18, R19, and R20 are independently selected from the group consisting of hydrogen, halogen, hydroxyl, and C1-6alkyl, t is 1-6, and u is 0-6; phenyl; benzyl; pyridinyl; pyrimidinyl; pyrazinyl; benzimidazolyl; benzothiazolyl; benzotriazolyl; naphthaloyl; quinolinyl; indolyl; thiadiazolyl; triazolyl; 4-methylpiperidin-1-yl; 4-methylpiperazin-1-yl; substituted phenyl; substituted benzyl; substituted pyridinyl; substituted pyrimidinyl; substituted pyrazinyl; substituted benzimidazolyl; substituted benzothiazolyl; substituted benzotriazolyl; substituted naphthaloyl; substituted quinolinyl; substituted indolyl; substituted thiadiazolyl; substituted triazolyl; substituted 4-methylpiperidin-1-yl; or substituted 4-methylpiperazin-1-yl wherein the substituents are selected from one or more members of the group consisting of C1-6alkyl, haloC1-alkyl, halogen, sulfonic acid, phosphonic acid, hydroxyl, carboxylic acid, amine, amidine, N-(2-aminopyrimidine)sulfonyl, N-(aminopyridine)sulfonyl, N-(aminopyrazine)sulfonyl, N-(2-aminopyrimidine)carbonyl, N-(aminopyridine)carbonyl, N-(aminopyrazine)carbonyl, N-(2-aminopyrimidine)phosphonyl, N-(2-aminopyridine)phosphonyl, N-(aminopyrazine)phosphonyl, N-(aminobenzimidazolyl)sulfonyl, N-(aminobenzothiazolyl)sulfonyl, N-(aminobenzotriazolyl)sulfonyl, N-(aminoindolyl)sulfonyl, N-(aminothiazolyl)sulfonyl, N-(aminotriazolyl)sulfonyl, N-(amino-4-methylpiperidinyl)sulfonyl, N-(amino-4-methylpiperazinyl)sulfonyl, N-(aminobenzimidazolyl)carbonyl, N-(aminobenzothiazolyl)carbonyl, N-(aminobenzotriazolyl)carbonyl, N-(aminoindolyl)carbonyl, N-(aminothiazolyl)carbonyl, N-(aminotriazolyl)carbonyl, N-(amino-4-methylpiperidinyl)carbonyl, N-(amino-4-methylpiperazinyl)carbonyl, N-(2-aminobenzimidazolyl)phosphonyl, N-(2-aminobenzothiazolyl)phosphonyl, N-(2-aminobenzotriazolyl)phosphonyl, N-(2-aminoindolyl)phosphonyl, N-(2-aminothiazolyl)phosphonyl, N-(2-aminotriazolyl)phosphonyl, N-(amino-4-methylpiperidinyl) phosphonyl, N-(amino-4-methylpiperazinyl) phosphonyl, acetamide, nitrile, thiol, C1-6alkyldisulfide, C1-6alkylsulfide, phenyl disulfide, urea, C1-6alkylurea, phenylurea, thiourea, C1-6alkylthiourea, phenylthiourea, substituted C1-6alkyldisulfide, substituted phenyldisulfide, substituted C1-6alkylurea, substituted C1-6alkylthiourea, substituted phenylurea, and substituted phenylthiourea wherein the C1-6alkyldisulfide, phenyldisulfide, C1-6alkylurea, C1-6alkylthiourea, phenylurea, and phenylthiourea substituents are selected from the group consisting of C1-6alkyl, haloC1-6alkyl, halogen, hydroxyl, carboxylic acid, sulfonic acid, phosphonic acid, amine, amidine, acetamide, and nitrile; b is 1-5; p is 1-5; R21 is hydrogen; R22 is hydroxyl, sulfonic acid, phosphonic acid, carboxylic acid, thioC1-6alkylcarbonyl, thioC1-6alkylaminocarbonyl, C1-6alkyldisulfide, phenyldisulfide, —C(O)N H(CH2)1-6—SO3H, —C(O)NH(CH2)1-6—P(O)(OH)2, —OR23, −NH—R23, —C(O)NH—(CH2)d—R23—S—(CH2)d—R23, —(CH2)d—R23, urea, C1-6alkylurea, phenylurea, thiourea, C1-6alkylthiourea, phenylthiourea, substituted C1-6alkyldisulfide, substituted phenyldisulfide, substituted C1-6alkylurea, substituted, C1-6alkylthiourea substituted phenylurea or substituted phenylthiourea wherein the substituents are selected from the group consisting of C1-6alkyl, haloC1-6alkyl, halogen, hydroxyl, carboxylic acid, sulfonic acid, phosphonic acid, amine, amidine, acetamide, and nitrile, where d is 0-8; R23 is thioC1-6alkylcarbonyl, C1-6alkyl, substituted C1-6alkyl where the alkyl substituents are selected from one or more members of the group consisting of C1-6alkyl, halo C1-6alkyl, halogen, hydroxyl, carboxylic acid, sulfonic acid, phosphonic acid, amine, amidine, acetamide, nitrile, thiol, C1-6alkyldisulfide, C1-6alkylsulfide, phenyldisulfide, urea, C1-6alkylurea, phenylurea, thiourea, C1-6alkylthiourea, phenylthiourea, substituted C1-6alkyldisulfide, substituted phenyldisulfide, substituted C1-6alkylurea, substituted phenylurea, substituted C1-6alkylthiourea, and substituted phenylthiourea wherein the C1-6alkyldisulfide, phenyldisulfide, C1-6alkylurea, C1-6alkylthiourea, phenylurea, and phenylthiourea substituents are selected from the group consisting of C1-6alkyl, haloC1-6alkyl, halogen, hydroxyl, carboxylic acid, sulfonic acid, phosphonic acid, amine, amidine, acetamide, and nitrile; —(CR24R25)q—(CHR26)m—SO3H where R24, R25, and R26 are independently selected from the group consisting of hydrogen, halogen, hydroxyl, and C1-6alkyl, q is 1-6, and m is 0-6 —(CH2)n—S—S—(CH2)xNH—C(O)CR27CH2, where R is hydrogen or C1-6alkyl, n is 1-6, and x is 1-6; —(CR28R29)t(CHR30)u—P(O)(OH)2 where R28, R29, and R30 are independently selected from the group consisting of hydrogen, halogen, hydroxyl, and C1-6alkyl, t is 1-6, and u is 0-6; phenyl; benzyl; pyridinyl; pyrimidinyl; pyrazinyl; benzimidazolyl; benzothiazolyl; benzotriazolyl; naphthaloyl; quinolinyl; indolyl; thiadiazolyl; triazolyl; 4-methylpiperidin-1-yl; 4-methylpiperazin-1-yl; substituted phenyl; substituted benzyl; substituted pyridinyl; substituted pyrimidinyl; substituted pyrazinyl; substituted benzimidazolyl; substituted benzothiazolyl; substituted benzotriazolyl; substituted naphthaloyl; substituted quinolinyl; substituted indolyl; substituted thiadiazolyl; substituted triazolyl; substituted 4-methylpiperidin-1-yl; or substituted 4-methylpiperazin-1-yl, wherein the substituents are selected from one or more members of the group consisting of C1-6alkyl, haloC1-6alkyl, halogen, sulfonic acid, phosphonic acid, hydroxyl, carboxylic acid, amine, amidine, N-(2-aminopyrimidine)sulfonyl, N-(aminopyridine)sulfonyl, N-(aminopyrazine)sulfonyl, N-(2-aminopyrimidine)carbonyl, N-(aminopyridine)carbonyl, N-(aminopyrazine)carbonyl, N-(2-aminopyrimidine)phosphonyl, N-(2-aminopyridine)phosphonyl, N-(aminopyrazine)phosphonyl, N-(aminobenzimidazolyl)sulfonyl, N-(aminobenzothiazolyl)sulfonyl, N-(aminobenzotriazolyl)sulfonyl, N-(aminoindolyl)sulfonyl, N-(aminothiazolyl)sulfonyl, N-(aminotriazolyl)sulfonyl, N-(amino-4-methylpiperidinyl)sulfonyl, N-(amino-4-methylpiperazinyl)sulfonyl, N-(aminobenzimidazolyl)carbonyl, N-(aminobenzothiazolyl)carbonyl, N-(aminobenzotriazolyl)carbonyl, N-(aminoindolyl)carbonyl, N-(aminothiazolyl)carbonyl, N-(aminotriazolyl)carbonyl, N-(amino-4-methylpiperidinyl)carbonyl, N-(amino-4-methylpiperazinyl)carbonyl, N-(2-aminobenzimidazolyl)phosphonyl, N-(2-aminobenzothiazolyl)phosphonyl, N-(2-aminobenzotriazolyl)phosphonyl, N-(2-aminoindolyl)phosphonyl, N-(2-aminothiazolyl)phosphonyl, N-(2-aminotriazolyl)phosphonyl, N-(amino-4-methylpiperidinyl) phosphonyl, N-(amino-4-methylpiperazinyl) phosphonyl, acetamide, nitrile, thiol, C1-6alkyldisulfide, C1-6alkylsulfide, phenyl disulfide, urea, C1-6alkylurea, phenylurea, thiourea, C1-6alkylthiourea, phenylthiourea, substituted C1-6alkyldisulfide, substituted phenyldisulfide, substituted C1-6alkylurea, substituted C1-6alkylthiourea, substituted phenylurea, and substituted phenylthiourea wherein the C1-6alkyldisulfide, phenyldisulfide, C1-6alkylurea, C1-6alkylthiourea, phenylurea, and phenylthiourea substituents are selected from the group consisting of C1-6alkyl, haloC1-6alkyl, halogen, hydroxyl, carboxylic acid, sulfonic acid, phosphonic acid, amine, amidine, acetamide, and nitrile; w is 0-1; Y is oxygen or sulfur; R31 is hydrogen or C1-6alkyl; R32 is hydroxyl, sulfonic acid, phosphonic acid, carboxylic acid, thioC1-6alkylcarbonyl, thioC1-6alkylaminocarbonyl, —C(O)NH—(CH2)d—R33, —O—R33, −NH—R33, —S—(CH2)d—R33, —(CH2)d—R33, C1-6alkyldisulfide, phenyldisulfide, urea, C1-6alkylurea, phenylurea, thiourea, C1-6alkylthiourea, phenylthiourea, C1-6alkylamine, phenylamine, substituted C1-6alkyldisulfide, substituted phenyldisulfide, substituted phenylurea, substituted C1-6alkylamine, substituted phenylamine, substituted phenylthiourea, substituted C1-6alkylurea or substituted C1-6alkylthiourea wherein the substitutents are selected from the group consisting of C1-6alkyl, haloC1-6alkyl, halogen, hydroxyl, carboxylic acid, sulfonic acid, phosphonic acid, amine, amidine, acetamide, and nitrile where d is 0-8; R33 is thioC1-6alkylcarbonyl, C1-6alkyl, substituted C1-6alkyl where the alkyl substituents are selected from one or more members of the group consisting of C1-6alkyl, halo C1-6alkyl, halogen, hydroxyl, carboxylic acid, sulfonic acid, phosphonic acid, amine, amidine, acetamide, nitrile, thiol, C1-6alkyldisulfide, C1-6alkylsulfide, phenyldisulfide, urea, C1-6alkylurea, phenylurea, thiourea, C1-6alkylthiourea, phenylthiourea, substituted C1-6alkyldisulfide, substituted phenyldisulfide, substituted C1-6alkylurea, substituted phenylurea, substituted C1-6alkylthiourea or substituted phenylthiourea wherein the C1-6alkyldisulfide, phenyldisulfide, C1-6alkylurea, C1-6alkylthiourea, phenylurea, and phenylthiourea substituents are selected from the group consisting of C1-6alkyl, haloC1-6alkyl, halogen, hydroxyl, carboxylic acid, sulfonic acid, phosphonic acid, amine, amidine, acetamide, and nitrile; —(CR34R35)q—(CHR36)m—SO3H where R34, R35, and R36 are independently selected from the group consisting of hydrogen, halogen, hydroxyl, and C1-6alkyl, q is 1-6, and m is 0-6; —(CH2)n—S—S—(CH2)xNH—C(O)CR37CH2, where R37 is hydrogen or C1-6alkyl, n is 1-6, and x is 1-6; —(CR38R39)t—(CHR40)u—P(O)(OH)2 where R38, R39, and R40 are independently selected from the group consisting of hydrogen, halogen, hydroxyl, and C1-6alkyl, t is 1-6, and u is 0-6; phenyl; benzyl; pyridinyl; pyrimidinyl; pyrazinyl; benzimidazolyl; benzothiazolyl; benzotriazolyl; naphthaloyl; quinolinyl; indolyl; thiadiazolyl; triazolyl; 4-methylpiperidin-1-yl; 4-methylpiperazin-1-yl; substituted phenyl; substituted benzyl; substituted pyridinyl; substituted pyrimidinyl; substituted pyrazinyl; substituted benzimidazolyl; substituted benzothiazolyl; substituted benzotriazolyl; substituted naphthaloyl; substituted quinolinyl; substituted indolyl; substituted thiadiazolyl; substituted triazolyl; substituted 4-methylpiperidin-1-yl; or substituted 4-methylpiperazin-1-yl, wherein the substituents are selected from one or more members of the group consisting of C1-6alkyl, haloC1-alkyl, halogen, sulfonic acid, phosphonic acid, hydroxyl, carboxylic acid, amine, amidine, N-(2-aminopyrimidine)sulfonyl, N-(aminopyridine)sulfonyl, N-(aminopyrazine)sulfonyl, N-(2-aminopyrimidine)carbonyl, N-(aminopyridine)carbonyl, N-(aminopyrazine)carbonyl, N-(2-aminopyrimidine)phosphonyl, N-(2-aminopyridine)phosphonyl, N-(aminopyrazine)phosphonyl, N-(aminobenzimidazolyl)sulfonyl, N-(aminobenzothiazolyl)sulfonyl, N-(aminobenzotriazolyl)sulfonyl, N-(aminoindolyl)sulfonyl, N-(aminothiazolyl)sulfonyl, N-(aminotriazolyl)sulfonyl, N-(amino-4-methylpiperidinyl)sulfonyl, N-(amino-4-methylpiperazinyl)sulfonyl, N-(aminobenzimidazolyl)carbonyl, N-(aminobenzothiazolyl)carbonyl, N-(aminobenzotriazolyl)carbonyl, N-(aminoindolyl)carbonyl, N-(aminothiazolyl)carbonyl, N-(aminotriazolyl)carbonyl, N-(amino-4-methylpiperidinyl)carbonyl, N-(amino-4-methylpiperazinyl)carbonyl, N-(2-aminobenzimidazolyl)phosphonyl, N-(2-aminobenzothiazolyl)phosphonyl, N-(2-aminobenzotriazolyl)phosphonyl, N-(2-aminoindolyl)phosphonyl, N-(2-aminothiazolyl)phosphonyl, N-(2-aminotriazolyl)phosphonyl, N-(amino-4-methylpiperidinyl) phosphonyl, N-(amino-4-methylpiperazinyl) phosphonyl, acetamide, nitrile, thiol, C1-6alkyldisulfide, C1-6alkylsulfide, phenyl disulfide, urea, C1-6alkylurea, phenylurea, thiourea, C1-6alkylthiourea, phenylthiourea, substituted C1-6alkyldisulfide, substituted phenyldisulfide, substituted C1-6alkylurea, substituted C1-6alkylthiourea, substituted phenylurea, and substituted phenylthiourea wherein the C1-6alkyldisulfide, phenyldisulfide, C1-6alkylurea, C1-6alkylthiourea, phenylurea, and phenylthiourea substituents are selected from the group consisting of C1-6alkyl, haloC1-6alkyl, halogen, hydroxyl, carboxylic acid, sulfonic acid, phosphonic acid, amine, amidine, acetamide, and nitrile; R41 is hydrogen, C1-6alkyl, phenyl, C1-6alkylcarbonyl, phenylcarbonyl, substituted C1-6alkyl, substituted phenyl, substituted C1-6alkylcarbonyl or substituted phenylcarbonyl, wherein the substituents are selected from the group consisting of C1-6alkyl, haloC1-6alkyl, halogen, hydroxyl, carboxylic acid, sulfonic acid, phosphonic acid, amine, amidine, acetamide, and nitrile.
- 2. The method of claim 1 wherein said ratio is at least about 0.5.
- 3. The method of claim 1 wherein the lens comprises silver in an amount which is at least about 90% of the target silver concentration.
- 4. The method of claim 1 wherein said at least one lens forming component comprises at least about 30 weight percent of said reactive monomer mixture.
- 5. The method of claim 1 wherein said at least one lens forming component comprises at least about 50 weight percent of said reactive monomer mixture.
- 6. The method of claim 4 wherein said at least one lens forming component comprises at least two lens forming components having similar solubilities.
- 7. The method of claim 1 wherein the ligand monomer is a monomer of Formula I and,
R1 is hydrogen or C1-3alkyl; R2 is NH—R3; d is 0; R3 is substituted phenyl, —(CR4R5)q—(CHR6)m—SO3H, —(CR8R9)t—(CHR10)u—P(O)(OH)2 or —(CH2)n—S—S—(CH2)xNH—C(O)CR7CH2; R4-6 are independently selected from the group consisting of hydrogen or C, 3alkyl; q is 1-3; m is 1-3; R7-10 are independently selected from the group consisting of hydrogen or C1-3alkyl; t is 1-3; u is 1-3; n is 2-4; and x is 2-4.
- 8. The method of claim 1 wherein the lens is a soft contact lens.
- 9. The method of claim 1 wherein the lens comprises about 0.01 to about 20 weight percent ligand monomer.
- 10. The method of claim 1 wherein the lens comprises about 0.01 to about 3 weight percent ligand monomer.
- 11. The method of claim 1 wherein the lens comprises about 100 to about 2000 ppm ligand monomer.
- 12. The method of claim 1 wherein the lens is a silicone hydrogel.
- 13. The method of claim 1 wherein, the lens comprises a formulation selected from the group consisting of etafilcon A, balafilcon, A, acquafilcon A, lenefilcon A, galyfilcon A, senofilcon A and lotrafilcon A.
- 14. The method of claim 1 wherein,
R1 is hydrogen or methyl; R2 is NH—R3; R3 is —(CR4R5)q—(CHR6)m—SO3H, —(CR8R9)t13 (CHR10)u—P(O)(OH)2 or —(CH2)n—S—S—(CH2)xNH—C(O)CHR7CH2; R4-6 are independently hydrogen or methyl; q is 1-2; m is 1-2; R7 is hydrogen; R8-10 are independently hydrogen or methyl; t is 1; u is 1-2; n is 2-3; and x is 2-3.
- 15. The method of claim 1 wherein the ligand monomer is selected from the group consisting of
- 16. The method of claim 1 wherein the antimicrobial lens comprises about 10 ppm to about 4,000 ppm silver.
- 17. The method of claim 1 wherein the antimicrobial lens comprises about 30 ppm to about 2000 ppm silver.
- 18. The method of claim 1 wherein the antimicrobial lens comprises about 30 ppm to about 1000 ppm silver.
- 19. The method of claim 1 wherein the lens is a silicone hydrogel and the ligand monomer is
- 20. The method of claim 19 wherein silver is present at about 30 ppm to about 2000 ppm and the ligand monomer is present at about 0.01 to about 3 weight percent.
- 21. The method of claim 13 wherein the ligand monomer is
- 22. The method of claim 21 wherein silver is present in the antimicrobial lens at about 30 ppm to about 2000 ppm and the ligand monomer is present at about 0.01 to about 3 weight percent.
- 23. The method of claim 21 wherein the lens formulation is etafilcon A or acquafilcon A.
- 24. The method of claim 1 wherein the silver solution is aqueous silver nitrate having a concentration of about 0.1 μg/mL to about 0.3 g/mL.
- 25. The method of claim 1 wherein, treating comprises soaking the lens with or in a silver solution.
- 26. The method of claim 25 wherein, the lens is soaked in the silver solution for about 2 minutes to about 2 hours.
- 27. The method of claim 1 wherein, treating comprises storing the lens in the silver solution for about 20 minutes to about 5 years.
- 28. The method of claim 1 wherein said monomer mix further comprises at least one initiator.
- 29. The method of claim 28 wherein said initiator comprises at least one photoinitiator.
- 30. The method of claim 29 wherein the curing step comprises an initiator concentration and light intensity sufficient to provide the reactivity ratio of at least about 0.45.
- 31. The method of claim 30 wherein the initiator concentration is at least about 0.4 weight % and said intensity is at least about 4 mW/cm2.
- 32. The method of claim 30 wherein the initiator concentration is at least about 0.9 weight % and said intensity is at least about 1 mW/cm2.
- 33. The method of claim 30 wherein the initiator concentration is at least about 0.4 weight % and said intensity is at least about 6 mW/cm2.
- 34. The method of claim 30 wherein the initiator concentration is at least about 0.9 weight % and said intensity is at least about 4 mW/cm2.
- 35. The method of claim 30 wherein the initiator concentration about 0.4 to about 2 weight % and said intensity is at least about 4 mW/cm2.
- 36. The method of claim 1 wherein said ligand monomer is selected from the monomers of Formula II.
- 37. The method of claim 36 wherein,
a is 1-2, R11 is hydrogen or C1-3alkyl, R12 is sulfonic acid, carboxylic acid, phosphonic acid, C1-6alkyldisulfide, C1-6alkylsulfide, phenyldisulfide, substiuted phenyldisulfide or NH—R13, R13 is thioC1-6alkylcarbonyl.
- 38. The method of claim 36 wherein the monomer of Formula II is selected from the group consisting of
- 39. The method of claim 1 wherein said ligand monomer is selected from the group consisting of monomers of Formula III.
- 40. The method of claim 39 wherein,
p is 1-3; b is 1-2; R21 is hydrogen; R22 is sulfonic acid, phosphonic acid, carboxylic acid, thioC1-6alkylcarbonyl, thioC1-6alkylaminocarbonyl, C1-6alkyldisulfide, C1-6alkylsulfide, phenyldisulfide, substiuted phenyldisulfide, H3OS—(CH2)1-6NHC(O) or (HO)2(O)P—(CH2)1-6NHC(O)—.
- 41. The method of claim 39 wherein the monomer of Formula III is selected from the group consisting of
- 42. The method of claim 1 wherein the ligand monomer is selected from the group consisting of monomers of Formula IV.
- 43. The method of claim 42 wherein,
w is 0-1; R31 is hydrogen; R32 is amine, C1-3alkylamine, phenylamine, substituted phenylamine; thioC1-3alkylcarbonyl; and R41 is hydrogen.
- 44. The method of claim 42 wherein the ligand monomer is selected from the group consisting of
RELATED INVENTIONS
[0001] This patent application claims priority from U.S. Ser. No. 10/028,400, filed on Dec. 20, 2001.
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
10028400 |
Dec 2001 |
US |
Child |
10703770 |
Nov 2003 |
US |