CA2592011A1 - Polymerizable surfactants and their use as device forming comonomers - Google Patents

Polymerizable surfactants and their use as device forming comonomers Download PDF

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Publication number
CA2592011A1
CA2592011A1 CA002592011A CA2592011A CA2592011A1 CA 2592011 A1 CA2592011 A1 CA 2592011A1 CA 002592011 A CA002592011 A CA 002592011A CA 2592011 A CA2592011 A CA 2592011A CA 2592011 A1 CA2592011 A1 CA 2592011A1
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CA
Canada
Prior art keywords
ophthalmic device
group
mixtures
meth
end terminal
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
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CA002592011A
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French (fr)
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CA2592011C (en
Inventor
Jeffrey G. Linhardt
Joseph C. Salamone
Daniel M. Ammon, Jr.
Daniel J. Hook
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Bausch and Lomb Inc
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Individual
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Publication of CA2592011A1 publication Critical patent/CA2592011A1/en
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Publication of CA2592011C publication Critical patent/CA2592011C/en
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Classifications

    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses
    • G02B1/043—Contact lenses

Abstract

This invention describes the use of polymerizable surfactants as comonomers in forming ophthalmic devices such as contact lenses, intraocular lenses, corneal implants, etc.

Claims (30)

1. An ophthalmic device comprising:

a polymerized comonomer mixture comprising at least one polymerizable surfactant selected from the group consisting of poloxamers having at least one end terminal functionalized, reverse poloxamers having at least one end terminal functionalized, poloxamines having at least one end terminal functionalized, reverse poloxamines having at least one end terminal functionalized and mixtures thereof.
2. The ophthalmic device of claim 1 wherein the ophthalmic device is a contact lens.
3. The ophthalmic device of claim 2 wherein the contact lens is a rigid gas permeable contact lens.
4. The ophthalmic device of claim 2 wherein the lens is a soft contact lens.
5. The ophthalmic device of claim 2 wherein the lens is a hydrogel contact lens.
6. The ophthalmic device of claim 1 wherein the lens is an intraocular lens.
7. The ophthalmic device of claim 6 wherein the lens is a phakic intraocular lens.
8. The ophthalmic device of claim 6 wherein the lens is an aphakic intraocular lens.
9. The ophthalmic device of claim 1 wherein the device is a corneal implant.
10. The ophthalmic device of claim 1 further comprising as part of the comonomer mixture an organo silicon compound.
11. The ophthalmic device of claim 10 wherein the silicon compound is selected from the group consisting of siloxanyl (meth)acrylate, siloxanyl (meth)acrylamide, siloxynyl vinyl carbamate, polymerizable siloxane oligomers and macromonomers and mixtures thereof.
12. The ophthalmic device of claim 10 further comprising as part of the monomer mixture at least one member selected from the group consisting of crosslinking agents, internal wetting agents, hydrophilic monomers and toughening agents.
13. The ophthalmic device of claim 12 wherein the hydrophilic monomers are selected from the group consisting of hydrophilic acrylic-, methacrylic-, itaconic-, styrenyl-, acrylamido-, methacrylamido- and vinyl-containing monomers and mixtures thereof.
14. The ophthalmic device of claim 13 wherein the hydrophilic monomers are selected from the group consisting of monomers containing the acrylic group represented by the formula:

wherein X is hydrogen or methyl and Y is --O--, --OQ--, --NH--, --NQ-- and --NH(Q)--, and Q is an alkyl or substituted alkyl group; and mixtures thereof.
15. The ophthalmic device of claim 13 wherein the vinyl-containing hydrophilic monomers are selected from the group consisting of N-vinyllactams, N-vinylpyrrolidone, N-vinyl-N-methylacetamide, N-vinyl-N-ethylacetamide, N-vinyl-N-ethylformamide, N-vinylformamide, and mixtures thereof.
16. The ophthalmic device of claim 13 wherein the hydrophilic monomers are selected from the group consisting of as N,N-dimethylacrylamide , 2-hydroxyethyl methacrylate, glycerol methacrylate, 2-hydroxyethyl methacrylamide, methacrylic acid, acrylic acid and mixtures thereof.
17. The opthalmic device of claim 1 further comprising as part of the comonomer mixture an ethylenically unsaturated hydrophilic monomer selected from the group consisting of ethylenically unsaturated polyoxyalkylenes, ethylenically unsaturated polyacrylamides, ethylenically unsaturated polyvinylpyrrolidones, ethylenically unsaturated polyvinyl alcohols, ethylenically unsaturated poly (hydroxyethyl methacrylate), ethylenically unsaturated N-alkyl-N-vinyl acetamides and mixtures thereof.
18. The ophthalmic device of claim 17 wherein the ethylenic unsaturation is provided by a group selected from (meth)acrylate, (meth)acrylamide, styrenyl, alkenyl, vinyl carbonate, vinyl carbamate groups and mixtures thereof.
19. The ophthalmic device of claim 1 further comprising hydrophobic monomers.
20. The ophthalmic device of claim 19 wherein the hydrophobic monomer is selected from the group consisting of alkyl (meth)acrylates, N-alkyl (meth)acrylamides, alkyl vinylcarbonates, alkyl vinylcarbamates, fluoroalkyl (meth)acrylates, N-fluoroalkyl (meth)acrylamides, N-fluoroalkyl vinylcarbonates, N-fluoroalkyl vinylcarbamates, silicone-containing (meth)acrylates, (meth)acrylamides, vinyl carbonates, vinyl carbamates, styrenic monomers such as styrene, alpha-methyl styrene, .rho.-methyl styrene, .rho.-t-butyl monochloro styrene, and .rho.-t-butyl dichloro styrene;
polyoxypropylene (meth)acrylates, methyl methacrylate, dodecyl methacrylate, octafluoropentyl methacrylate, perfluorooctyl methacrylate, methacryoyl oxypropyl tris(trimethylsiloxy)silane (TRIS) and mixtures thereof.
21. The ophthalmic device of claim 1 further comprising a free radical thermal polymerization initiators selected from the group consisting of organic peroxides such as acetyl peroxide, lauroyl peroxide, decanoyl peroxide, stearoyl peroxide, benzoyl peroxide, t-butyl peroxypivalate, peroxydicarbonate and mixtures thereof.
22. The ophthalmic device of claim 1 further comprising a UV initiator.
23. A method of forming an ophthalmic device comprising:

providing a polymerizable mixture comprising a comonomer mixture comprising at least one polymerizable surfactant selected from the group consisting of poloxamers having at least one end terminal functionalized, reverse poloxamers having at least one end terminal functionalized, poloxamines having at least one end terminal functionalized, reverse poloxamines having at least one end terminal functionalized and mixtures thereof;

subjecting the polymerizable mixture to polymerizing conditions; and, shaping the polymerizable mixture into the desired shape of the ophthalmic device.
24. The method of claim 23 wherein the step of shaping occurs after subjecting the polymerizable mixture to polymerization conditions.
25. The method of claim 23 wherein the step of shaping comprises cutting, lathing, polishing and combinations thereof.
26. The method of claim 23 further comprising the step of placing the polymerizable mixture comprising a comonomer mixture comprising at least one polymerizable surfactant selected from the group consisting of poloxamers having at least one end terminal functionalized, reverse poloxamers having at least one end terminal functionalized, poloxamines having at least one end terminal functionalized, reverse poloxamines having at least one end terminal functionalized and mixtures thereof in a mold prior to the step of subjecting the polymerizable mixture to polymerization conditions.
27. The method of claim 26 wherein the step of polymerizing is conducted in a mold selected from the group consisting of spinning molds and stationary molds.
28. The method of claim 23 wherein the step of polymerizing is conducted in an appropriate mold or vessel to form buttons, plates or rods.
29. The method of claim 23 further comprising the step of hydrating the polymerized mixture.
30. The method of claim 23 wherein the ophthalmic device formed is selected from the group consisting of rigid gas permeable contact lens, soft contact lens, intraocular lens, phakic intraocular lens, aphakic intraocular lens and corneal implant.
CA2592011A 2004-12-22 2005-11-03 Polymerizable surfactants and their use as device forming comonomers Active CA2592011C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US11/020,541 2004-12-22
US11/020,541 US8197841B2 (en) 2004-12-22 2004-12-22 Polymerizable surfactants and their use as device forming comonomers
PCT/US2005/039731 WO2006068705A1 (en) 2004-12-22 2005-11-03 Polymerizable surfactants and their use as device forming comonomers

Publications (2)

Publication Number Publication Date
CA2592011A1 true CA2592011A1 (en) 2006-06-29
CA2592011C CA2592011C (en) 2010-07-20

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CA2592011A Active CA2592011C (en) 2004-12-22 2005-11-03 Polymerizable surfactants and their use as device forming comonomers

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US (3) US8197841B2 (en)
EP (1) EP1828813B1 (en)
JP (1) JP4732464B2 (en)
CN (1) CN101088029B (en)
AT (1) ATE457469T1 (en)
CA (1) CA2592011C (en)
DE (1) DE602005019322D1 (en)
ES (1) ES2338681T3 (en)
MX (1) MX2007007361A (en)
WO (1) WO2006068705A1 (en)

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Also Published As

Publication number Publication date
CA2592011C (en) 2010-07-20
US20120157565A1 (en) 2012-06-21
CN101088029A (en) 2007-12-12
DE602005019322D1 (en) 2010-03-25
EP1828813B1 (en) 2010-02-10
US8377464B2 (en) 2013-02-19
US8197841B2 (en) 2012-06-12
EP1828813A1 (en) 2007-09-05
CN101088029B (en) 2011-05-18
ES2338681T3 (en) 2010-05-11
US20060275342A1 (en) 2006-12-07
JP4732464B2 (en) 2011-07-27
MX2007007361A (en) 2007-10-04
JP2008525847A (en) 2008-07-17
ATE457469T1 (en) 2010-02-15
US20060134169A1 (en) 2006-06-22
WO2006068705A1 (en) 2006-06-29

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