Amphiphilic polysiloxane prepolymers and uses thereof

• US 8,987,403 B2
• Filed: 08/30/2013
• Issued: 03/24/2015
• Est. Priority Date: 07/30/2010
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Chang, Frank, Scott, Robert, Huang, Jinyu, Medina, Arturo N., Smith, Dawn A., Sanders, Laura A., Pruitt, John Dallas
• Primary Examiner(s): MOORE, MARGARET G
• Application Number:
  US14/014,631
• Publication Number:
  US 20140005430A1
• Time in Patent Office: 571 Days
• Field of Search: 528/32, 526/279
• US Class Current: 528/32
• CPC Class Codes: C08F 220/20 of polyhydric alcohols or phenols , e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
• CPC Class Codes: C08F 220/54 Amides , e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
• CPC Class Codes: C08F 220/56 Acrylamide; Methacrylamide
• CPC Class Codes: C08F 230/085 the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08G 2210/00 Compositions for preparing hydrogels
• CPC Class Codes: C08G 77/388 containing nitrogen
• CPC Class Codes: C08G 77/458 containing polyurethane sequences
• CPC Class Codes: C08L 101/14 the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
• CPC Class Codes: C08L 2205/02 containing two or more polymers of the same C08L -group
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

The present invention provides an amphiphilic polysiloxane prepolymer which comprises hydrophilic monomeric units derived from at least one hydrophilic vinylic monomer, polysiloxane crosslinking units derived from at least one polysiloxane crosslinker having at least two terminal ethylenically-unsaturated groups, dangling polysiloxane chains each of which is terminated with one ethylenically unsaturated group, and chain-transfer units derived from a chain transfer agent other than a RAFT agent. A prepolymer of the invention is suitable for making hydrogel contact lenses. The present invention is also related to hydrogel contact lenses made from an amphiphilic polysiloxane prepolymer of the invention and to processes for preparing an amphiphilic polysiloxane prepolymer of the invention and for making silicone hydrogel contact lenses.

Claims

1. A partially ethylenically-functionalized polysiloxane, which is a mixture of reaction products obtained by reacting an ethylenically functionalizing vinylic monomer having a first reactive functional group with a linear functional polysiloxane compound having two terminal second reactive functional groups at a molar equivalent ratio, R_Equivalent, of from about 40% to about 97%, wherein each first reactive functional group reacts with one second reactive functional group in the presence or absence of a coupling agent to form a covalent bond or linkage, wherein the mixture of reaction product comprises (R_Equivalent)²×

100% by mole of a linear polysiloxane crosslinkers having two terminal ethylenically-unsaturated groups, 2×

R_Equivalent×

(1−

R_Equivalent)×

100% by mole of a polysiloxane vinylic monomer or macromer having one terminal second reactive functional group and one terminal ethylenically-unsaturated group, and (1−

R_Equivalent)×

(1−

R_Equivalent)×

100% by mole of unreacted linear polysiloxane compound with two terminal second reactive functional groups.

2. The partially ethylenically-functionalized polysiloxane of claim 1, wherein R_Equivalent is from about 50% to about 95%.

3. The partially ethylenically-functionalized polysiloxane of claim 1, wherein R_Equivalent is from about 60% to about 92%.

4. The partially ethylenically-functionalized polysiloxane of claim 1, wherein R_Equivalent is from about 70% to about 90%.

5. The partially ethylenically-functionalized polysiloxane of claim 1, wherein the linear functional polysiloxane compound is defined by formula (1)

FG-G₁-PDMS-G₂-FG 

 

(1)

CR(-G₁-PDMS-G₂-FG)_a1 

 

(2)

in which

G₁ and G₂ independent of each other are a linear or branched C₁-C₁₀ alkylene divalent radical, a divalent radical of alk′

-O_qalk- in which q is an integer of from 1 to 5 and alk and alk′

independent of each other is a C₁-C₆ alkylene divalent radical, or a divalent radical of -R′

₁-X₁-E-X₂-R′

₂-in which R′

₁ and R′

₂ independent of each other is a linear or branched C₁-C₁₀ alkylene divalent radical or a divalent radical of alk′

-O_qalk- as defined above, X₁ and X₂ independent of each other are a linkage selected from the group consisting of

6. The partially ethylenically-functionalized polysiloxane of claim 5, wherein the ethylenically functionalizing vinylic monomer is selected from the group consisting of C₁ to C₆ hydroxylalkyl (meth)acrylate, C₁ to C₆ hydroxyalkyl (meth)acrylamide, C₁ to C₆ aminoalkyl (meth)acrylate, allylalcohol, allylamine, C₁ to C₆ aminoalkyl (meth)acrylamide, aziridinyl C₁-C₁₂ alkyl (meth)acrylate (e.g., 2-(1-aziridinyl) ethyl (meth)acrylate, 3-(1-aziridinyl) propyl (meth)acrylate, 4-(1-aziridinyl) butyl (meth)acrylate, 6-(1-aziridinyl) hexyl (meth)acrylate, or 8-(1-axiridinyl) octyl (meth)acrylate), glycidyl (meth)acrylate, C₁ to C₆ alkyl (meth)acrylic acid, (meth)acrylic acid halide (—

COX, X═

Cl, Br, or I), C₁ to C₆ isocyanatoalkyl (meth)acrylate, 2-vinyl-4,4-dimethyl-1,3-oxazolin-5-one, 2-isopropenyl-4,4-dimethyl-1,3-oxazolin-5-one, 2-vinyl-4-methyl-4-ethyl-1,3-oxazolin-5-one, 2-isopropenyl-4-methyl-4-butyl-1,3-oxazolin-5-one, 2-vinyl-4,4-dibutyl-1,3-oxazolin-5-one, 2-isopropenyl-4-methyl-4-dodecyl-1,3-oxazolin-5-one, 2-isopropenyl-4,4-diphenyl-1,3-oxazolin-5-one, 2-isopropenyl-4,4-pentamethylene-1,3-oxazolin-5-one, 2-isopropenyl-4,4-tetramethylene-1,3-oxazolin-5-one, 2-vinyl-4,4-diethyl-1,3-oxazolin-5-one, 2-vinyl-4-methyl-4-nonyl-1,3-oxazolin-5-one, 2-isopropenyl-4-methyl-4-phenyl-1,3-oxazolin-5-one, 2-isopropenyl-4-methyl-4-benzyl-1,3-oxazolin-5-one, 2-vinyl-4,4-pentamethylene-1,3-oxazolin-5-one, and 2-vinyl-4,4-dimethyl-1,3-oxazolin-6-one, with 2-vinyl-4,4-dimethyl-1,3-oxazolin-5-one (VDMO), 2-isopropenyl-4,4-dimethyl-1,3-oxazolin-5-one (IPDMO), and combinations thereof.