BIOMEDICAL DEVICES CONTAINING INTERNAL WETTING AGENTS

• US 20080015282A1
• Filed: 03/30/2007
• Published: 01/17/2008
• Est. Priority Date: 09/10/2001
• Status: Active Grant

• Current Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Original Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Inventors: Ford, James, Hill, Gregory, Steffen, Robert, McCabe, Kevin, Vanderlaan, Douglas, Molock, Frank, Alli, Azaam
• Granted Patent: US 8,450,387 B2
• Time in Patent Office: Days
• US Class Current: 523/107
• CPC Class Codes: A61L 2430/16 for reconstruction of eye parts, e.g. intraocular lens, cornea
• CPC Class Codes: A61L 27/18 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61L 27/26 Mixtures of macromolecular compounds
• CPC Class Codes: A61L 27/52 Hydrogels or hydrocolloids
• CPC Class Codes: C08F 251/00 Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
• CPC Class Codes: C08F 265/04 on to polymers of esters
• CPC Class Codes: C08F 271/00 Macromolecular compounds obtained by polymerising monomers on to polymers of nitrogen-containing monomers as defined in group C08F26/00
• CPC Class Codes: C08F 271/02 on to polymers of monomers containing heterocyclic nitrogen
• CPC Class Codes: C08F 283/06 on to polyethers, polyoxymethylenes or polyacetals C08F283/004 takes precedence
• CPC Class Codes: C08F 283/12 on to polysiloxanes
• CPC Class Codes: C08F 290/06 Polymers provided for in subclass C08G
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08F 291/00 Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses
• CPC Class Codes: G02C 7/022 Ophthalmic lenses having special refractive features achieved by special materials or material structures G02C7/049 takes precedence

Abstract

This invention includes a wettable biomedical device containing a high molecular weight hydrophilic polymer and a hydroxyl-functionalized silicone-containing monomer.

Claims

1. A biomedical device formed from a reaction mixture comprising a high molecular weight hydrophilic polymer and an effective amount of an hydroxyl-functionalized silicone-containing monomer.

2. The biomedical device of claim 1 wherein the effective amount of said hydroxyl-functionalized silicone-containing monomer is about 5% to about 90%

3. The biomedical device of claim 1 wherein the device is a silicone hydrogel contact lens.

4. The biomedical device of claim 1 comprising about 1% to about 15% high molecular weight hydrophilic polymer.

5. The biomedical device of claim 2 wherein the effective amount of hydroxyl-functionalized silicone-containing monomer is about 10% to about 80%.

6. The biomedical device of claim 1 wherein said hydroxyl-functionalized silicone-containing monomer is a compound of Formula I or II

wherein:

n is an integer between 3 and 35

R¹ is hydrogen, C_1-6alkyl,

R²,R³, and R⁴, are independently, C_1-6alkyl, triC_1-6alkylsiloxy, phenyl, naphthyl, substituted C_1-6alkyl, substituted phenyl, or substituted naphthyl

where substitutents for said substituted C_1-6alkyl are selected from one or more members of the group consisting of C_1-6alkoxycarbonyl, C_1-6alkyl, C_1-6alkoxy, amide, halogen, hydroxyl, carboxyl, C_1-6alkylcarbonyl and formyl, and

where substitutents for said substituted phenyl, or substituted naphthyl are selected from one or more members of the group consisting of C_1-6alkoxycarbonyl, C_1-6alkyl, C_1-6alkoxy, amide, halogen, hydroxyl, carboxyl, C_1-6alkylcarbonyl and formyl;

R⁵ is a hydroxyl, an alkyl group containing one or more hydroxyl groups;

or (CH₂(CR⁹R¹⁰)_yO)_x)—

R¹¹ wherein y is 1 to 5, preferably 1 to 3, x is an integer of 1 to 100, preferably 2 to 90 and more preferably 10 to 25;

R⁹-R¹¹ are independently selected from H, alkyl having up to 10 carbon atoms and alkyls having up to 10 carbon atoms substituted with at least one polar functional group,

R⁶ is a divalent group comprising up to 20 carbon atoms;

R⁷ is a monovalent group that can undergo free radical or cationic polymerization, comprising up to 20 carbon atoms; and

R⁸ is a divalent or trivalent group comprising up to 20 carbon atoms.

7. The biomedical device of claim 1 wherein said hydroxyl-functionalized silicone-containing monomer is selected from the group consisting of 2-propenoic acid, 2-methyl-2-hydroxy-3-[3-[1,3,3,3-tetramethyl-1-[trimethylsilyl)oxy]disiloxanyl]propoxy]propyl ester, (3-methacryloxy-2-hydroxypropyloxy)propyltris(trimethylsiloxy)silane, (2-methacryloxy-3-hydroxypropyloxy)propylbis(trimethylsiloxy)methylsilane and mixtures thereof.

11. The biomedical device of claim 1, wherein the hydroxyl-functionalized silicone-containing monomer has a monomer compatibility index of greater than about 0.5.

12. The biomedical device of claim 1, wherein the high molecular weight hydrophilic polymer is poly-N-vinylpyrrolidone.

167. The biomedical device of claim 1 wherein said hydroxyl-functionalized silicone-containing monomer is selected from the group consisting of 2-propenoic acid, 2-methyl-2-hydroxy-3-[3-[1,3,3,3-tetramethyl-1-[trimethylsilyl)oxy]disiloxanyl]propoxy]propyl ester, (3-methacryloxy-2-hydroxypropyl)propyltris(trimethylsiloxy)silane, (2-methacryloxy-3-hydroxypropyloxy)propylbis(trimethylsiloxy)methylsilane(3-methacryloxy-2-hydroxypropyloxy)propyltris(trimethylsiloxy)silane, bis-3-methacryloxy-2-hydroxypropyloxypropylpolydimethylsiloxane, 3-methacryloxy-2-(2-hydroxyethoxy)propyloxy)propylbis(trimethylsiloxy)methylsilane and mixtures thereof.

13. A method of preparing a biomedical device comprising mixing a high molecular weight hydrophilic polymer and an effective amount of a hydroxyl-functionalized silicone-containing monomer to form a clear solution, and curing said solution.

14. A silicone hydrogel formed from a reaction mixture comprising a high molecular weight hydrophilic polymer and an effective amount of an hydroxyl-functionalized silicone-containing monomer.

66. A method comprising the steps of (a) mixing reactive components comprising at least one high molecular weight hydrophilic polymer and an effective amount of at least one hydroxyl-functionalized silicone-containing monomer and (b) curing the product of step (a) to form a biomedical device.

67. The method of claim 66 wherein said biomedical device comprises an ophthalmic device.

68. The method of claim 67 wherein said ophthalmic device is a silicone hydrogel contact lens.

69. The method of claim 67 wherein said reactive components are mixed in the presence of a diluent to form a reaction mixture.

70. The method of claim 69 wherein said diluent is selected from the group consisting of ethers, esters, alkanes, alkyl halides, silanes, amides, alcohols and mixtures thereof.

71. The method of claim 69 wherein said diluent selected from the group consisting of amides, alcohols and mixtures thereof.

72. The method of claim 69 wherein said diluent selecting the group consisting of secondary and tertiary alcohols and mixtures thereof.

73. The method of claim 69 wherein said diluent selecting the group consisting of tetrahydrofuran, ethyl acetate, methyl lactate, i-propyl lactate, ethylene chloride, octamethylcyclotetrasiloxane, dimethyl formamide, dimethyl acetamide, dimethyl propionamide, N methyl pyrrolidinone mixtures thereof and mixtures of any of the foregoing with at least one alcohol.

74. The method of claim 71 wherein said diluent comprises at least one alcohol having at least 5 carbon atoms.

75. The method of claim 71 wherein said diluent comprises at least one alcohol having at least 6 carbons atoms.

76. The method of claim 69 wherein said diluents are inert and easily displaceable with water.

77. The method of claim 69 wherein said diluent comprises at least one alcohol selected from the group consisting of tert-butanol, tert-amyl alcohol, 2-butanol, 2-methyl-2-pentanol, 2,3-dimethyl-2-butanol, 3-methyl-3-pentanol, 3-ethyl-3-pentanol, 3,7-dimethyl-3-octanol and mixtures thereof.

78. The method of claim 69 wherein said diluent is selected from the group consisting of hexanol, heptanol, octanol, nonanol, decanol, tert-butyl alcohol, 3-methyl-3-pentanol, isopropanol, t amyl alcohol, ethyl lactate, methyl lactate, i-propyl lactate, 3,7-dimethyl-3-octanol, dimethyl formamide, dimethyl acetamide, dimethyl propionamide, N methyl pyrrolidinone and mixtures thereof.

79. The method of claim 69 wherein said diluent is selected from the group consisting of 1-ethoxy-2-propanol, 1-methyl-2-propanol, t-amyl alcohol, tripropylene glycol methyl ether, isopropanol, 1-methyl-2-pyrrolidone, ethyl lactate, N,N-dimethylpropionamide, dipropylene glycol methyl ether and mixtures thereof.

80. The method of claim 69 wherein said diluent is present in an amount less than about 50 weight %, based upon the reaction mixture.

81. The method of claim 69 wherein said diluent is present in an amount less than about 40 weight % based upon the reaction mixture.

82. The method of claim 69 wherein said diluent is present in an amount between about 10 and about 30 weight % based upon the reaction mixture.

83. The method of claim 69 wherein said diluent is water soluble at processing conditions and said process further comprises (c) removing said lens from a mold in which said lens was cured and (d) hydrating said lens, wherein both steps (c) and (d) are performed in aqueous solutions which comprise water as a substantial component.

84. The method of claim 69 wherein said reaction mixture further comprises at least one initiator.

85. The method of claim 84 wherein said curing is conducted via heat, exposure to radiation or a combination thereof.

86. The method of claim 84 wherein said curing is conducted via irradiation comprises ionizing and/or actinic radiation and said initiator comprises at least one photoinitiator.

87. The method of claim 86 wherein said radiation comprises light having a wavelength of about 200 to about 500 nm and said initiator is selected from the group consisting of aromatic alpha-hydroxy ketones, alkoxyoxybenzoins, acetophenones, acyl phosphine oxides, mixtures of tertiary amines and diketones, and mixtures thereof.

88. The method of claim 86 wherein said initiator is selected from the group consisting of 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, bis(2,6-dimethoxybenzoyl)-2,4-4-trimethylpentyl phosphine oxide, bis(2,4,6-trimethylbenzoyl)-phenylphosphineoxide, 2,4,6-trimethylbenzyldiphenyl phosphine oxide and 2,4,6-trimethylbenzyoyl diphenylphosphine oxide, benzoin methyl ester, combinations of camphorquinone and ethyl 4-(N,N-dimethylamino)benzoate and mixtures thereof.

89. The method of claim 84 wherein said initiator is present in the reaction mixture in amounts effective to initiate polymerization of the reaction mixture.

90. The method of claim 84 wherein said initiator is present in the reaction mixture in amounts from about 0.1 to about 2 weight percent based upon said reactive components.

91. The method of claim 86 wherein said curing is conducted via visible light irradiation.

92. The method of claim 91 wherein said initiator comprises 1-hydroxycyclohexyl phenyl ketone, bis(2,6-dimethoxybenzoyl)-2,4-4-trimethylpentyl phosphine oxide and mixtures thereof.

93. The method of claim 91 wherein said initiator comprises bis(2,4,6-trimethylbenzoyl)-phenylphosphineoxide.

94. The method of claim 91 wherein said reactive components further comprises at least one UV absorbing compound.

95. The method of claim 91 wherein said curing step is conducted at a cure intensity between about 0.1 and about 6 mW/cm².

96. The method of claim 91 wherein said curing step is conducted at a cure intensity of between about. 0.2 mW/cm² to about 3 mW/cm².

97. The method of claims 95 wherein said curing step further comprises a cure time of at least about 1 minute.

98. The method of claims 95 wherein said curing step further comprises a cure time of between about 1 and about 60 minutes.

99. The method of claim 95 wherein said curing step further comprises a cure time of between about 1 and about 30 minutes.

100. The method of claim 97 wherein said curing step is conduct at a temperature greater than about 25°

C.

101. The method of claim 97 wherein said curing step is conduct at a temperature between about 25°

C. and 70°

C.

102. The method of claim 97 wherein said curing step is conduct at a temperature between about 40°

C. and 70°

C.

103. The method of claim 69 wherein said reaction mixture is cured in a mold and said method further comprises the step of deblocking said ophthalmic device from said mold.

104. The method of claim 103 wherein said reaction mixture further comprises at least one low molecular weight hydrophilic polymer.

105. The method of claim 104 wherein said low molecular weight hydrophilic polymer has a number average molecular weight of less than about 40,000 Dalton.

106. The method of claim 104 wherein said low molecular weight hydrophilic polymer has a number average molecular weight of less than about 20,000 Dalton.

107. The method of claim 104 wherein the low molecular weight polymer is selected from the group consisting of water soluble polyamides, lactams and polyethylene glycols, and mixtures thereof.

108. The method of claim 104 wherein the low molecular weight polymer is selected from the group consisting poly-vinylpyrrolidone, polyethylene glycols, poly 2 ethyl-2-oxazoline and mixtures thereof.

109. The method of claim 104 wherein the low molecular weight hydrophilic polymer is present in amounts up to about 20 weight % based upon the reaction mixture.

110. The method of claim 104 wherein the low molecular weight hydrophilic polymer is present in amounts between about 5 and about 20 weight % based upon the reaction mixture.

111. The method of claim 103 wherein said deblocking is conducted using an aqueous solution.

112. The method of claim 111 wherein said aqueous solution further comprises at least one surfactant.

113. The method of claim 112 wherein said surfactant comprises at least one non-ionic surfactant.

114. The method of claim 112 wherein said surfactant comprises polyoxyethylene (20) sorbitan monostearate, or ethoxylated methyl glucoside dioleate.

115. The method of claim 112 wherein said surfactant is present in amounts up to about 10,000 ppm.

116. The method of claim 112 wherein said surfactant is present in amounts between about 500 ppm and about 1500 ppm.

117. The method of claim 112 wherein said surfactant is present in amounts between about 100 and about 1200 ppm.

118. The method of claim 103 wherein said aqueous solution comprises at least one organic solvent.

119. The method of claim 103 wherein said deblocking is conducted at a temperature between about ambient and about 100°

C.

120. The method of claim 103 wherein said deblocking is conducted at a temperature between about 70°

C. and about 95°

C.

121. The method of claim 103 wherein said deblocking is conducted using agitation.

122. The method of claim 121 wherein said agitation comprises sonication.

123. A method comprising the steps of (a) mixing reactive components comprising a high molecular weight hydrophilic polymer and an effective amount of a hydroxyl-functionalized silicone containing monomer and (b) curing the product of step (a) at or above a minimum gel time, to form a wettable biomedical device.

124. The method of claim 123 wherein said device is a ophthalmic lens.

125. The method of claim 123 wherein said device is a contact lens.

126. The method of claim 125 wherein said wettability comprises an advancing dyanimc contact angle of about 70°

or less.

127. The method of claim 125 wherein said wettability comprises an advancing dynamic contact angle of about 60°

or less.

128. The method of claim 125 wherein said wettability comprises a tear film break up time of at least about 7 seconds.

129. The method of claim 125 wherein said reactive components further comprises at least one initiator

130. The method of claim 129 wherein said cure is conducted via irradiation and said conditions comprise an initiator concentration and cure intensity effective to provide said minimum gel time.

131. The method of claim 129 wherein said initiator is present in an amount up to about 1% based upon all reactive components.

132. The method of claim 129 wherein said initiator is present in an amount less than about 0.5% based upon all reactive components.

133. The method of claim 130 wherein said cure is conducted via irradiation at an intensity of less than about 5 mW/cm².

134. The method of claim 130 wherein said gel time is at least about 30 seconds.

135. The method of claim 123 wherein said gel time is at least about 35 seconds.

161. The method of claim 125 wherein said wettability comprises a contact angle of about 80°

or less.

136. An ophthalmic device comprising at least one hydroxyl-functionalized silicone-containing monomer and an amount of high molecular weight hydrophilic polymer sufficient to provide said device, without a surface treatment, with an advancing dynamic contact angle of less than about 80°

.

139. The ophthalmic device claim 136 wherein said device is a silicone hydrogel contact lens.

140. The ophthalmic device of claim 136 wherein said hydroxyl-functionalized silicone containing monomer is present in a compatibilizing effective amount.

141. The ophthalmic device of claim 136 wherein said hydroxyl-functionalized silicone containing monomer is present in an amount between about 5% to about 90%

142. The biomedical device of claim 136 comprising about 1% to about 15% high molecular weight hydrophilic polymer.

143. The biomedical device of claim 136 further comprising 0 to about 80 weight % at least one additional silicone containing monomer.

144. The biomedical device of claim 136 further comprising 0 to about 70 weight % at least one hydrophilic monomer.

145. The biomedical device of claim 136 comprising about 1% to about 15% high molecular weight hydrophilic polymer;

about 5 to about 90 weight % hydroxyl-functionalized silicone containing monomer;

0 to about 80 weight % additional silicone containing monomer and 0 to about 70 weight % hydrophilic monomer.

146. The biomedical device of claim 136 further comprising a haze value of less than about 100.

147. The biomedical device of claim 136 further comprising a haze value of less than about 50.

137. An ophthalmic device comprising at least one hydroxyl-functionalized silicone-containing monomer and an amount of high molecular weight hydrophilic polymer sufficient to provide said device, without a surface treatment, with an advancing dynamic contact angle which is at least about 10% lower than an advancing dynamic contact angle for an ophthalmic device which does not contain said hydrophilic polymer.

138. An ophthalmic device comprising at least one hydroxyl-functionalized silicone-containing monomer and an amount of high molecular weight hydrophilic polymer sufficient to provide said device, without a surface treatment, with tear film break up time after about one day of wear of at least about 7 seconds.

152. A method for improving the wettability of an ophthalmic device formed from a reaction mixture comprising adding at least one high molecular weight hydrophilic polymer and an effective amount of at least one compatibilizing monomer to said reaction mixture.

153. The method of claim 152 wherein said compatibilizing monomer has a compatibility index of greater than about 0.5.

154. The method of claim 152 wherein said compatibilizing monomer has a compatibility index of greater than about 1.

155. The method of claim 152 wherein said compatibilizing monomer comprises at least one siloxane group.

156. A method for improving the wettability of an ophthalmic device formed from a reaction mixture comprising incorporating at least one high molecular weight hydrophilic polymer and an effective amount of at least one hydroxyl-functionalized silicone containing monomer to said reaction mixture.

157. The method of claim 156 wherein said compatibilizing monomer has a compatibility index of greater than about 0.5.

158. The method of claim 156 wherein said compatibilizing monomer has a compatibility index of greater than about 1.

159. The method of claim 156 wherein said compatibilizing monomer has a Si to OH ratio of less than about 15:

1.

160. The method of claim 156 wherein said compatibilizing monomer has a Si to OH ratio of between about 1:

1 to about 10;

1

162. A device comprising a silicone hydrogel contact lens which is substantially free from surface deposition without surface modification.

163. A silicone hydrogel formed from a reaction mixture comprising high molecular weight hydrophilic polymer and an effective amount of hydroxyl-functionalized silicone-containing monomer selected from the group consisting of

(3-methacryloxy-2-hydroxypropyloxy)propyltris(trimethylsiloxy)silane, (2-methacryloxy-3-hydroxypropyloxy)propylbis(trimethylsiloxy)methylsilane (3-methacryloxy-2-hydroxypropyloxy)propyltris(trimethylsiloxy)silane, bis-3-methacryloxy-2-hydroxypropyloxypropyl polydimethylsiloxane, 3-methacryloxy-2-(2-hydroxyethoxy)propyloxy)propylbis(trimethylsiloxy)methylsilane, N,N,N′

,N′

-tetrakis(3-methacryloxy-2-hydroxypropyl)-α

,ω

-bis-3-aminopropyl-polydimethylsiloxane and mixtures thereof.

8. The biomedical device of claim 16 wherein the effective amount of said hydroxyl-functionalized silicone-containing monomer is about 20% to about 50%.

9. The biomedical device of claim 16 further comprising about 10% to about 40% additional silicone containing monomer, about 10% to about 50% hydrophilic monomers, and about 3% to about 15% high molecular weight hydrophilic polymer.

10. The biomedical device of claim 9, wherein the device is a soft contact lens.

15. The silicone hydrogel of claim 163 wherein said hydrophilic polymer is selected from the group consisting of polyamides, polylactones, polyimides, polylactams, functionalized polyamides, functionalized polylactones, functionalized polyimides, functionalized polylactams, and mixtures thereof.

16. The silicone hydrogel of claim 163 wherein said hydrophilic polymer is selected from the group consisting of poly-N-vinyl pyrrolidone, poly-N-vinyl-2-piperidone, poly-N-vinyl-2-caprolactam, poly-N-vinyl-3-methyl-2-caprolactam, poly-N-vinyl-3-methyl-2-piperidone, poly-N-vinyl-4-methyl-2-piperidone, poly-N-vinyl-4-methyl-2-caprolactam, poly-N-vinyl-3-ethyl-2-pyrrolidone, and poly-N-vinyl-4,5-dimethyl-2-pyrrolidone, polyvinylimidazole, poly-N-N-dimethylacrylamide, polyvinyl alcohol, polyacrylic acid, polyethylene oxide, poly 2 ethyl oxazoline, heparin polysaccharides, polysaccharides, mixtures and copolymers thereof.

17. The silicone hydrogel of claim 163 wherein said hydrophilic polymer comprises poly-N-vinylpyrrolidone.

18. The silicone hydrogel of claim 163 comprising about 1 to about 15 weight % high molecular weight hydrophilic polymer.

19. The silicone hydrogel of claim 163 comprising about 3 to about 15 weight % high molecular weight hydrophilic polymer.

20. The silicone hydrogel of claim 163 comprising about 5 to about 12 weight % high molecular weight hydrophilic polymer.

21. The silicone hydrogel of claim 163 wherein said hydroxyl-functionalized silicone-containing monomer is a compound of Formula I or II

wherein:

n is an integer between 3 and 35

R¹ is hydrogen, C_1-6alkyl,

R²,R³, and R⁴, are independently, C_1-6alkyl, triC_1-6alkylsiloxy, phenyl, naphthyl, substituted C_1-6alkyl, substituted phenyl, or substituted naphthyl

where substitutents for said substituted C_1-6alkyl are selected from one or more members of the group consisting of C_1-6alkoxycarbonyl, C_1-6alkyl, C_1-6alkoxy, amide, halogen, hydroxyl, carboxyl, C_1-6alkylcarbonyl and formyl, and

where substitutents for said substituted phenyl, or substituted naphthyl are selected from one or more members of the group consisting of C_1-6alkoxycarbonyl, C_1-6alkyl, C_1-6alkoxy, amide, halogen, hydroxyl, carboxyl, C_1-6alkylcarbonyl and formyl;

R⁵ is a hydroxyl, an alkyl group containing one or more hydroxyl groups, or (CH₂(CR⁹R¹⁰)_yO)_x)—

R¹¹ wherein y is 1 to 5, preferably 1 to 3, x is an integer of 1 to 100, preferably 2 to 90 and more preferably 10 to 25;

R⁹-R¹¹ are independently selected from H, alkyl having up to 10 carbon atoms and alkyls having up to 10 carbon atoms substituted with at least one polar functional group;

R⁶ is a divalent group comprising up to 20 carbon atoms;

R⁷ is a monovalent group that can undergo free radical or cationic polymerization, comprising up to 20 carbon atoms, and

R⁸ is a divalent or trivalent group comprising up to 20 carbon atoms.

22. The silicone hydrogel of claim 163 or 164 wherein the effective amount of hydroxyl-functionalized silicone-containing monomer is about 20% to about 50%.

23. The silicone hydrogel of claim 21 wherein said hydroxyl-functionalized silicone-containing monomer is selected from the group consisting of 2-propenoic acid, 2-methyl-2-hydroxy-3-[3-[1,3,3,3-tetramethyl-1-[trimethylsilyl)oxy]disiloxanyl]propoxy]propyl ester, (3-methacryloxy-2-hydroxypropyloxy)propyltris(trimethylsiloxy)silane, (2-methacryloxy-3-hydroxypropyloxy)propylbis(trimethylsiloxy)methylsilane and mixtures thereof.

24. The silicone hydrogel of claim 163 or 164 further comprising at least one additional silicone containing monomer.

25. The silicone hydrogel of claim 24 wherein said additional silicone containing monomers are selected from the group consisting of amide analogs of 3-methacryloxypropyltris(trimethylsiloxy)silane;

siloxane vinyl carbamate analogs, siloxane vinyl carbonate analogs, and siloxane containing monomers, combinations and oligomers thereof.

26. The silicone hydrogel of claim 24 wherein said additional silicone containing monomers are selected from the group consisting of 3-methacryloxypropyltris(trimethylsiloxy)silane, monomethacryloxypropyl terminated polydimethylsiloxanes, polydimethylsiloxanes, 3-methacryloxypropylbis(trimethylsiloxy)methylsilane, methacryloxypropylpentamethyl disiloxane and combinations thereof.

27. The silicone hydrogel of claim 24 wherein said additional silicone containing monomers are present in an amount of 0 to about 80 weight %.

28. The silicone hydrogel of claim 24 wherein said additional silicone containing monomers are present in an amount of about 5 to about 60%.

29. The silicone hydrogel of claim 24 wherein said additional silicone containing monomers are present in an amount of about 10 to about 40%.

30. The silicone hydrogel of claim 163 or 164 further comprising at least one hydrophilic monomer.

31. The silicone hydrogel of claim 30 wherein said at least one hydrophilic monomer comprises at least one acrylic group, vinyl group or a combination thereof.

32. The silicone hydrogel of claim 31 wherein said acrylic group has the formula CH₂═

CRCOX, where R is hydrogen or C_1-6alkyl and X is O or N.

33. The silicone hydrogel of claim 30 wherein said at least one hydrophilic monomer is selected from the group consisting of N,N-dimethylacrylamide, 2-hydroxyethyl methacrylate, glycerol methacrylate, 2-hydroxyethyl methacrylamide, polyethyleneglycol monomethacrylate, methacrylic acid, acrylic acid, N-vinyl pyrrolidone, N-vinyl-N-methyl acetamide, N-vinyl-N-ethyl acetamide, N-vinyl-N-ethyl formamide, N-vinyl formamide, hydrophilic vinyl carbonate monomers, vinyl carbamate monomers, hydrophilic oxazolone monomers, polydextran and copolymers and combinations thereof.

34. The silicone hydrogel of claim 30 wherein said at least one hydrophilic monomer comprises at least one polyoxyethylene polyol having one or more of the terminal hydroxyl groups replaced with a functional group containing a polymerizable double bond.

35. The silicone hydrogel of claim 34 wherein said at least one hydrophilic monomer is selected from the group consisting of polyethylene glycol, ethoxylated alkyl glucoside, and polyethylene polyols having one or more terminal polymerizable olefinic groups bonded to the polyethylene polyol.

36. The silicone hydrogel of claim 30 wherein said at least one hydrophilic monomer is selected from the group consisting of N,N-dimethylacrylamide, 2-hydroxyethyl methacrylate, glycerol methacrylate, 2-hydroxyethyl methacrylamide, N-vinylpyrrolidone, polyethyleneglycol monomethacrylate, methacrylic acid, acrylic acid and combinations thereof.

37. The silicone hydrogel of claim 30 wherein said at least one hydrophilic monomer comprises N,N-dimethylacrylamide.

38. The silicone hydrogel of claim 30 wherein said at least one hydrophilic monomer is present in amounts of about 0 to about 70 weight %.

39. The silicone hydrogel of claim 30 wherein said at least one hydrophilic monomer is present in amounts of about 5 to about 60 weight %.

40. The silicone hydrogel of claim 30 wherein said at least one hydrophilic monomer is present in amounts of about 10 to 50 weight %.

41. The silicone hydrogel of claim 163 or 164 comprising about 1 to about 15 weight % high molecular weight hydrophilic polymer and about 5 to about 90 weight % hydroxyl-functionalized silicone-containing monomer.

42. The silicone hydrogel of claim 163 or 164 comprising about 3 to about 15 weight % high molecular weight hydrophilic polymer and about 10 to about 80 weight % hydroxyl-functionalized silicone-containing monomer.

43. The silicone hydrogel of claim 15 comprising about 5 to about 12 weight % high molecular weight hydrophilic polymer and about 20 to about 50 weight % hydroxyl-functionalized silicone-containing monomer.

44. The silicone hydrogel of claim 163 or 164 further comprising 0 to about 80 weight % at least one additional silicone containing monomer.

45. The silicone hydrogel of claim 163 or 164 further comprising about 0 to about 70 weight % at least one hydrophilic monomer.

46. The silicone hydrogel of claim 44 comprising about 5 to about 60 weight % of said at least one additional silicone containing monomer.

47. The silicone hydrogel of claim 44 comprising about 10 to about 40 weight % of said at least one additional silicone containing monomer.

48. The silicone hydrogel of claim 45 comprising about 5 to about 60 weight % of said at least one hydrophilic monomer.

49. The silicone hydrogel of claim 45 comprising about 10 to about 50 weight % of said at least one hydrophilic monomer.

50. The silicone hydrogel of claim 163 or 164 comprising about 1% to about 15% high molecular weight hydrophilic polymer;

about 5 to about 90 weight % hydroxyl-functionalized silicone containing monomer;

5 to about 60 weight % additional silicone containing monomer and 5 to about 60 weight % hydrophilic monomer.

51. The silicone hydrogel of claim 163 or 164 comprising about 3% to about 15% high molecular weight hydrophilic polymer;

about 10 to about 80 weight % hydroxyl-functionalized silicone containing monomer;

5 to about 60 weight % additional silicone containing monomer and 5 to about 60 weight % hydrophilic monomer.

52. The silicone hydrogel of claim 163 or 164 comprising about 5% to about 12% high molecular weight hydrophilic polymer;

about 20 to about 50 weight % hydroxyl-functionalized silicone containing monomer;

5 to about 60 weight % additional silicone containing monomer and 50 to about 60 weight % hydrophilic monomer.

53. The silicone hydrogel of claim 163 or 164 comprising about 5% to about 12% high molecular weight hydrophilic polymer;

about 20 to about 50 weight % hydroxyl-functionalized silicone containing monomer;

10 to about 40 weight % additional silicone containing monomer and 10 to about 50 weight % hydrophilic monomer.

54. The silicone hydrogel of claim 163 or 164 wherein said hydrophilic polymer has a weight average molecular weight of at least about 100,000 daltons.

55. The silicone hydrogel of claim 163 or 164 wherein said hydrophilic polymer comprises at least one cyclic moiety along a backbone portion of said hydrophilic polymer.

56. The silicone hydrogel of claim 163 or 164 wherein said hydrophilic polymer is selected from the group consisting of polymers comprising cyclic amides, cyclic imides and combinations thereof.

57. An ophthalmic device comprising the silicone hydrogel of claim 163 or 164.

58. The opthalmic 163 or 164 device of claim 57 further comprising an advancing dynamic contact angle of less than about 70°

.

59. The ophthalmic 163 or 164 device of claim 57 further comprising an advancing dynamic contact angle of less than about 60°

.

60. The ophthalmic device of claim 57 further comprising, after about one day of wear, a tear film break up time of at least about 7 seconds and an oxygen permeability of at least about 50 barrers.

61. The ophthalmic device of claim 58 further comprising a modulus of less than about 90 psi.

62. The ophthalmic device of claim 58 further comprising a water content between about 10 and about 60%.

63. The ophthalmic device of claim 58 further comprising a water content between about 20 and about 55%.

64. The ophthalmic device of claims 58 further comprising a water content between about 25 and about 40%.

65. The ophthalmic device of claim 60 wherein said tear film breakup time is at least about 7 seconds after about 7 days of wear.

148. The silicone hydrogel of claim 50 wherein said hydroxyl-functionalized silicone containing monomer comprises 2-propenoic acid, 2-methyl-,2-hydroxy-3-[3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propoxy]propyl ester, said hydrophilic polymer comprises polyvinylpyrrolidone;

said additional silicone containing monomer comprises monomethacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane and said hydrophilic monomers comprise 2-hydroxyethyl methacryate and N,N-dimethylacrylamide.

149. The silicone hydrogel of claim 148 comprising the reaction product of about 28 weight % 2-propenoic acid, 2-methyl-,2-hydroxy-3-[3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propoxy]propyl ester, about 31 weight % monomethacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane about 24 weight % N,N-dimethylacrylamide, about 6 weight % 2-hydroxyethyl methacryate, about 1.5 weight % tetraethyleneglycoldimethacrylate, about 7 weight % polyvinylpyrrolidone, and up to about 1 weight % photoinitiator.

150. The silicone hydrogel of claim 148 comprising the reaction product of about 30 weight % 2-propenoic acid, 2-methyl-,2-hydroxy-3-[3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propoxy]propyl ester, about 23 weight % monomethacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane about 31 weight % N,N-dimethylacrylamide, about 7.5 weight % 2-hydroxyethyl methacryate, about 0.75 weight % ethyleneglycoldimethacrylate, about 6 weight % polyvinylpyrrolidone, and up to about 1 weight % photoinitiator.

151. The silicone hydrogel of claim 148 comprising the reaction product of about 30 weight % 2-propenoic acid, 2-methyl-,2-hydroxy-3-[3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propoxy]propyl ester, about 18 weight % monomethacryloxypropyl terminated mono-n-butyl terminated polydimethylsiloxane about 31 weight % N,N-dimethylacrylamide, about 9 weight % 2-hydroxyethyl methacryate, about 0.8 weight % ethyleneglycoldimethacrylate, about 6 weight % polyvinylpyrrolidone, and less than about 1 weight % photoinitiator.

165. The silicone hydrogel of claim 163 or 164 wherein said hydroxyl-functionalized silicone-containing monomer is present in an amount between about 5 weight % to about 90 weight %.

166. The silicone hydrogel of claim 163 or 164 wherein said hydroxyl-functionalized silicone-containing monomer is present in an amount between about 10 weight % to about 80 weight %.

168. A biomedical device formed from the silicone hydrogel of claim 163 or 164.

164. A silicone hydrogel formed from a reaction mixture comprising high molecular weight hydrophilic polymer and an effective amount of hydroxyl-functionalized silicone-containing monomer comprising bis-3-methacryloxy-2-hydroxypropyloxypropyl polydimethylsiloxane.