Method for making silicone hydrogel contact lenses

• US 20100258961A1
• Filed: 06/16/2009
• Published: 10/14/2010
• Est. Priority Date: 12/18/2008
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Turek, Richard Charles, Holland, Troy Vernon, Wu, Daqing, Vogt, Jürgen, Pruitt, John Dallas, Domschke, Angelika Maria, Qian, Xinming, Chang, Frank, Smith, Dawn A.
• Granted Patent: US 8,163,206 B2
• Time in Patent Office: Days
• US Class Current: 264/1.380
• CPC Class Codes: C08F 283/124 on to polysiloxanes having carbon-to-carbon double bonds
• 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 invention provide a method for making silicone hydrogel based on the Lightstream Technology from a monomer mixture with a curing time of less than about 100 seconds. The present invention is also related to silicone hydrogel contact lenses made according to methods of the invention.

Claims

1. A method for producing silicone hydrogel contact lenses, comprising the steps of:

providing a mold for making a soft contact lens, wherein the mold has a first mold half with a first molding surface defining the anterior surface of a contact lens and a second mold half with a second molding surface defining the posterior surface of the contact lens, wherein said first and second mold halves are configured to receive each other such that a cavity is formed between said first and second molding surfaces;

introduce a monomer mixture of lens-forming materials into the cavity, wherein the monomer mixture comprises at least one hydrophilic amide-type vinylic monomer, at least one siloxane-containing (meth)acrylamide monomer, at least one polysiloxane vinylic monomer or macromer, and from about 0.05% to about 1.5% by weight of a photoinitator, wherein the lens forming material is characterized by having an ability to be cured by a UV light having an UV-intensity of about 4.1 mW/cm² within about 100 seconds; and

irradiating, under a spatial limitation of actinic radiation, the lens-forming material in the mold for a time period of about 120 seconds or less, so as to crosslink the lens-forming material to form the silicone hydrogel contact lens, wherein the produced contact lens comprises an anterior surface defined by the first molding surface, an opposite posterior surface defined by the second molding surface, and a lens edge defined by the spatial limitation of actinic radiation.

2. The method of claim 1, wherein siloxane-containing (meth)acrylamide monomer is represented by formula (1)

3. The method of claim 2, wherein the monomer mixture comprises a polysiloxane-containing vinylic macromer of formula (4)

Q-X₁-G₁-PDMS-G₂

X₂-Q)_r  

 

(4)

in which

r is an integer of 0 or 1;

G₁ and G₂ independent of each other is 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—

X₄-E-X₅—

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, X₄ and X₅ independent of each other are a linkage selected from the group consisting of

4. The method of claim 2, wherein the hydrophilic amide-type vinylic monomer is selected from the group consisting of 2-acrylamidoglycolic acid, 2-acrylamido-2-methyl-1-propanesulfonic acid, 2-acrylamido-2-methyl-1-propanesulfonic acid or salt thereof, (3-acrylamidopropyl)trimethylammonium chloride, 3-acryloylamino-1-propanol, N-(butoxymethyl)acrylamide, N-tert-butylacrylamide, diacetone acrylamide, N,N-dimethylacrylamide, N,N-dimethylmethacrylamide, N-[3-(dimethylamino)propyl]methacrylamide, N-hydroxyethyl acrylamide, N-(hydroxymethyl)acrylamide, N-(isobutoxymethyl)acrylamide, N-isopropylacrylamide, N-isopropylmethacrylamide, methacrylamide, N-phenylacrylamide, N-[Tris(hydroxymethyl)methyl]acrylamide, N-methyl-3-methylene-2-pyrrolidone, and a mixture thereof.

5. The method of claim 3, wherein the siloxane-containing (meth)acrylamide monomer is selected from the group consisting of N-[tris(trimethylsiloxy)silylpropyl]methacrylamide, N-[tris(trimethylsiloxy)-silylpropyl]acrylamide, N-[tris(dimethylpropylsiloxy)silylpropyl]acrylamide, N-[tris(dimethylpropylsiloxy)silylpropyl]methacrylamide, N-[tris(dimethyl-phenylsiloxy)silylpropyl]acrylamide, N-[tris(dimethylphenylsiloxy)silylpropyl]methacrylamide, N-[tris(dimethylethylsiloxy)silylpropyl]acrylamide, N-[tris(dimethylethylsiloxy)silylpropyl]methacrylamide, N-(2-hydroxy-3-(3-(bis(trimethylsilyloxy)methylsilyl)propyloxy)propyl)-2-methyl acrylamide;

N-(2-hydroxy-3-(3-(bis(trimethylsilyloxy)methylsilyl)propyloxy)propyl)acrylamide;

N, N-bis[2-hydroxy-3-(3-(bis(trimethylsilyloxy)methylsilyl)propyloxy)propyl]-2-methyl acrylamide;

N, N-bis[2-hydroxy-3-(3-(bis(trimethylsilyloxy)methylsilyl)propyloxy)propyl]acrylamide;

N-(2-hydroxy-3-(3-(tris(trimethylsilyloxy)silyl)propyloxy)propyl)-2-methyl acrylamide;

N-(2-hydroxy-3-(3-(tris(trimethylsilyloxy)silyl)propyloxy)propyl)acrylamide;

N,N-bis[2-hydroxy-3-(3-(tris(trimethylsilyloxy)silyl)propyloxy)propyl]-2-methyl acrylamide;

N,N-bis[2-hydroxy-3-(3-(tris(trimethylsilyloxy)silyl)propyloxy)propyl]acrylamide;

N-[2-hydroxy-3-(3-(t-butyidimethylsilyl)propyloxy)propyl]-2-methyl acrylamide;

N-[2-hydroxy-3-(3-(t-butyldimethylsilyl)propyloxy)propyl]acrylamide;

N,N-bis[2-hydroxy-3-(3-(t-butyldimethylsilyl)propyloxy)propyl]-2-methyl acrylamide;

N,N-bis[2-hydroxy-3-(3-(t-butyidimethylsilyl)propyloxy)propyl]acrylamide.

6. The method of claim 3, wherein the monomer mixture comprises a polysiloxane-containing vinylic macromer of formula (4) in which D₁;

D₂ and D₃ independently of each other are a divalent radical of formula (6).

7. The method of claim 3, wherein the monomer mixture comprises a polymerizable UV-absorbing agent or a polymerizable latent UV-absorbing agent in an amount from about 0.2% to about 5.0% by weight.

8. The method of claim 7, wherein the monomer mixture comprises a polymerizable UV-absorbing agent which comprises a benzotriazole- and/or benzophenone-moiety.

9. The method of claim 8, wherein the photoinitiator is a benzoylphosphine oxide photoinitiator.

10. The method of claim 7, wherein the monomer mixture comprises a polymerizable latent UV-absorbing agent.

11. The method of claim 3, wherein at least one of the first and second molding surfaces is permeable to UV radiation and optionally the other molding surface is poorly permeable to UV radiation.

12. The method of claim 11, wherein the mold is a reusable mold comprising a mask which is fixed, constructed or arranged in, at or on the mold half having the radiation-permeable molding surface, wherein the mask is UV-impermeable or at least of poor UV-permeability compared with the UV-permeable molding surface, wherein the mask extends inwardly right up to the mold cavity and surrounds the mold cavity so as to screen all areas behind the mask with the exception of the mold cavity.

13. The method of claim 12, wherein the monomer mixture in the mold is irradiated under the spatial limitation of actinic radiation for a time period of about 50 seconds or less.

14. The method of claim 2, wherein the monomer mixture comprises (1) from about 10% to about 50% by weight of the hydrophilic amide-type vinylic monomer;

(2) from about 10% to about 40% by weight of the siloxane-containing acrylate or acrylamide or methacrylamide monomer;

(3) from about 10% to about 40% by weight of the polysiloxane-containing vinylic macromer;

(4) from about 0.1% to 1.3% by weight of a photoinitiator; and

(5) from 0 to 5% by weight of a polymerizable UV-absorbing agent or a polymerizable latent UV-absorbing agent, provided that components (1) to (5) and any additional components add up to 100% by weight.

15. A silicone hydrogel contact lens obtained according to claim 1.

16. The silicone hydrogel contact lens of claim 15, wherein the contact lens has at least one property selected from the group consisting of an oxygen permeability of preferably at least about 40 barrers, an elastic modulus of about 2.0 MPa or less, an Ionoflux Diffusion Coefficient, D, of at least about 1.5×

10<sup>−

6</sup> mm²/min, and a water content of preferably from about 15% to about 70%.

17. A method for producing silicone hydrogel contact lenses, comprising the steps of:

providing a mold for making a soft contact lens, wherein the mold has a first mold half with a first molding surface defining the anterior surface of a contact lens and a second mold half with a second molding surface defining the posterior surface of the contact lens, wherein said first and second mold halves are configured to receive each other such that a cavity is formed between said first and second molding surfaces;

introduce a monomer mixture of lens-forming materials into the cavity, wherein the monomer mixture comprises at least one hydrophilic amide-type vinylic monomer, at least one siloxane-containing acrylate monomer, at least one polysiloxane vinylic monomer or macromer, and from about 0.05% to about 1.5% by weight of a photoinitator, wherein the lens forming material is characterized by having an ability to be cured by a UV light having an UV-intensity of about 4.1 mW/cm² within about 100 seconds; and

irradiating, under a spatial limitation of actinic radiation, the lens-forming material in the mold for a time period of about 120 seconds or less, so as to crosslink the lens-forming material to form the silicone hydrogel contact lens, wherein the produced contact lens comprises an anterior surface defined by the first molding surface, an opposite posterior surface defined by the second molding surface, and a lens edge defined by the spatial limitation of actinic radiation.

18. A lens-forming composition suitable for making silicone hydrogel contact lenses according to a curing method based on a spatial limitation of actinic radiation, comprising:

at least one hydrophilic amide-type vinylic monomer;

at least one siloxane-containing vinylic monomer selected from the group consisting of siloxane-containing acrylate, siloxane-containing acrylamide, siloxane-containing methacrylamide; and

from about 0.05% to about 1.5% by weight of a photoinitator, provided that the total amount of all methacrylate monomer(s) in the lens-forming composition is less than about 10% by weight and is sufficient low so as to provide the lens forming composition with a characteristics of being able to be cured by a UV light having an UV-intensity of about 4.1 mW/cm² within a time period of less than about 100 seconds.