Method for producing MPS-compatible water gradient contact lenses

Patent metadata

Field	Value
Publication number	US-11029447-B2
Application number	US-201816204705-A
Country	US
Kind code	B2
Filing date	Nov 29, 2018
Priority date	Dec 13, 2017
Publication date	Jun 8, 2021
Grant date	Jun 8, 2021

Abstract

The invention is related to a process for producing contact lenses that not only comprise a water gradient structural configurations, but also have a minimized uptakes of polyquaternium-1 and a long-lasting surface hydrophilicity and wettability even after being undergone a simulated 30-days lens care regime.

First claim

What is claimed is:

1. A process for producing a contact lens, comprising the steps of:
(a) obtaining a contact lens precursor which is a coated contact lens which comprises a lens bulk material completely covered with an anchor layer of a polyanionic polymer which comprises at least 60% by mole of repeating units of at least one carboxyl-containing vinylic monomer; and
(b) heating, in the presence of at least one first polyaziridine which has a number average molecular weight of about 2000 Dalton or less and at least two aziridine groups, the contact lens precursor in a first aqueous solution which comprises a thermally-crosslinkable hydrophilic polymeric material which has thermally-crosslinkable groups, to and at a temperature from about 30° C. to about 140° C. for a period of time sufficient to obtain the contact lens,
wherein the contact lens comprise (i) a crosslink anchor layer thereon and (2) an outer surface hydrogel layer which is covalently attached to the crosslinked anchor layer, wherein the crosslinked anchor layer is obtained crosslinking the polyanionic polymer in the anchor layer via crosslinkers derived from said at least one polyaziridine in coupling reaction between at least two pair of aziridine and carboxyl groups, wherein the outer surface hydrogel layer is formed by crosslinking the thermally-crosslinked hydrophilic polymeric material, wherein the contact lens has a polyquaternium-1 uptake (“PU pz ”) of about 0.6 μg/lens or less.

2. The process of claim 1 , further comprising a step of soaking the contact lens precursor in a second aqueous solution comprising at least one second polyaziridine having a number average molecular weight of about 2000 Dalton or less and at least two aziridine groups.

3. The process of claim 2 , wherein the first aqueous solution further comprises said at least one first polyaziridine.

4. The process of claim 3 , wherein the first and second polyaziridines independent of each other are selected from a group consisting of trimethylolpropane tris(2-methyl-1-aziridinepropionate), pentaerythritol tris[3-(1-aziridinyl)propionate], trimethylolpropane tris(3-aziridinopropionate), a Michael reaction product of a vinylic crosslinker having at least three (meth)acryloyl groups and 2-methylaziridine, a Michael reaction product of a vinylic crosslinker having at least three (meth)acryloyl groups and aziridine, or a combination thereof.

5. The process of claim 4 , wherein the vinylic crosslinker is selected from the group consisting of trimethylolpropane triacrylate, pentaerythritol triacrylate, tris(2-hydroxyethyl)isocyanurate triacrylate, trimethylolpropane ethoxylate triacrylates, glyceryl propoxylate triacrylate, trimethylolpropane propoxylate triacrylates, pentaerythritol tetraacrylate, ditrimethylolpropane tetraacrylate, pentaerythritol ethoxylate tetraacrylate, dipentaerythritol pentaacrylate, caprolactone modified dipentaerythritol hexaacrylates, caprolactone modified dipentaerythritol pentaacrylate, ethoxylated glycerol triacrylate, ethoxylated trimethylolpropane trimethacrylate, propoxylated trimethylolpropane trimethacrylate, ethoxylated pentaerythritol trimethacrylate, ethoxylated pentaerythritol tetramethacrylate, ethoxylated dipentaerythritol trimethacrylate, ethoxylated dipentaerythritol tetramethacrylate, ethoxylated dipentaerythritol pentamethacrylate, ethoxylated dipentaerythritol hexamethacrylate, ethoxylated dipentaerythritol triacrylate, ethoxylated dipentaerythritol tetraacrylate, ethoxylated dipentaerythritol pentaacrylate, ethoxylated dipentaerythritol hexaacrylate, propoxylated pentaerythritol trimethacrylate, propoxylated pentaerythritol triacrylate, propoxylated pentaerythritol tetramethacrylate, propoxylated pentaerythritol tetraacrylate, propoxylated dipentaerythritol trimethacrylate, propoxylated dipentaerythritol tetramethacrylate, propoxylated dipentaerythritol pentamethacrylate, propoxylated dipentaerythritol hexamethacrylate, propoxylated dipentaerythritol triacrylate, propoxylated dipentaerythritol tetraacrylate, propoxylated dipentaerythritol pentaacrylate and propoxylated dipentaerythritol hexaacrylate, ethoxylated trimethyloylpropane triacrylamide, and combinations thereof.

6. The process of claim 5 , wherein the first and second aqueous solutions independent of each other comprise two polyaziridines, a first polyaziridine having at least two aziridine groups of

and a second polyaziridine having at least two aziridine groups of

and at least one hydrophilic moiety selected from the group consisting of —OH, —[OC 2 H 4 O] n1 —. —CONHR 1 , —CONR 1 —, and combinations thereof, wherein n1 is an integer of 1 to 10 and R 1 is hydrogen, methyl or ethyl.

7. The process of claim 6 , wherein the first and second aqueous solutions independent of each other comprise from about 0.01% to about 2.5% by weight of said at least one first or second polyaziridine.

8. The process of claim 6 , wherein the first aqueous solution is a lens packaging solution, wherein the step of heating is performed by autoclaving the contact lens precursor immersed in the lens packaging solution in a sealed lens package at a temperature of from about 115° C. to about 125° C. for approximately 20-90 minutes.

9. The process of claim 8 , wherein the lens packaging solution further comprises a partially hydrolyzed polyvinyl alcohol having a hydrolysis degree of hydrolysis of from about 80% to about 98%.

10. The process of claim 8 , wherein the lens packaging solution has a pH of from about 7.0 to about 9.0 before autoclaving and a pH of from about 6.5 to about 7.7 after autoclaving.

11. The process of claim 8 , wherein the first aqueous solution is obtained directly in the lens package by mixing a third aqueous solution and a fourth aqueous, wherein the third aqueous solution comprises the thermally-crosslinkable hydrophilic polymeric material.

12. The process of claim 11 , wherein the third aqueous solution is free of any polyaziridine.

13. The process of claim 11 , wherein the third aqueous solution further comprises said at least one polyaziridine.

14. The process of claim 11 , wherein the fourth aqueous solution comprises said at least one first polyaziridine.

15. The process of claim 11 , wherein the fourth aqueous solution is free of any polyaziridine.

16. The process of claim 11 , wherein said at least one carboxyl-containing vinylic monomer is acrylic acid, methacrylic acid, ethylacrylic acid, 2-(meth)acrylamidoglycolic acid, and combinations thereof.

17. The process of claim 11 , wherein the polyanionic polymer is polyacrylic acid, polymethacrylic acid, poly(ethylacrylic acid), poly(acrylic acid-co-methacrylic acid), poly[ethylacrylic acid-co-(meth)acrylic acid], poly(N,N-2-acrylamidoglycolic acid), poly[(meth)acrylic acid-co-acrylamide], poly[(meth)acrylic acid-co-vinylpyrrolidone], poly[ethylacrylic acid-co-acrylamide], poly[ethylacrylic acid-co-vinylpyrrolidone], poly[(meth)acrylic acid-co-vinylacetate], poly[ethylacrylic acid-co-vinylacetate], or combinations thereof.

18. The process of claim 11 , wherein the polyanionic polymer is a graft polymer which is grafted onto the inner layer or the lens bulk material, wherein the graft polymer comprises repeating units of at least one carboxyl-containing vinylic monomer which is acrylic acid, methacrylic acid, ethylacrylic acid, 2-(meth)acrylamidoglycolic acid, and comb

Assignees

• Novartis Ag
• Alcon Inc

Inventors

• Qiu Yongxing
• Pruitt John Dallas
• Samuel Newton T
• Chiang Chung-Yuan
• Driver-Scott Angela
• Dauenhauer Ciara
• Anand Rita

Classifications

• B29D11/00865

  Applying coatings; tinting; colouring (printing, marking or copying processes B41M; identification in general G09F3/00; producing decorative effects in general B44C; positioning or marking of lenses B24B13/0055) · CPC title

• B65B55/22

  Immersing contents in protective liquids · CPC title

• C08L2201/10

  Transparent films; Clear coatings; Transparent materials · CPC title

• G02C7/049 Primary

  Contact lenses having special fitting or structural features achieved by special materials or material structures · CPC title

• G02B1/043 Primary

  Contact lenses · CPC title