Method for producing MPS-compatible water gradient contact lenses

Patent metadata

Field	Value
Publication number	US-11029446-B2
Application number	US-201816204664-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 30-days lens care regime.

First claim

What is claimed is:

1. A process for producing contact lenses, comprising the steps of:
(a) obtaining a contact lens precursor which is a coated contact lens and has a first polyquaternium-1 uptake (“PU o ”), wherein the coated contact lens comprises a lens bulk material completely covered with an anchor layer of a polyanionic polymer and an outer surface hydrogel layer covalently attached to the anchor layer, wherein the polyanionic polymer comprises at least 60% by mole of repeating units of at least one carboxyl-containing vinylic monomer; and
(b) heating the contact lens precursor in an aqueous solution in the presence of at least one polyaziridine to and at a temperature from about 30° C. to about 140° C. for a period of time sufficient to obtain the contact lens having a second polyquaternium-1 uptake (“PU pz ”), wherein the polyaziridine having a number average molecular weight of about 2000 Dalton or less and at least two aziridine groups each of which is a mono-valent radical of formula

in which R1 is hydrogen, methyl or ethyl, wherein (PU o -PU pz )/PU o is at least 60%.

2. The process of claim 1 , wherein said at least one polyaziridine is 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.

3. The process of claim 2 , wherein the aqueous solution comprises 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.

4. The process of claim 3 , wherein the aqueous solution comprises from about 0.01% to about 2.5% by weight of said at least one polyaziridine.

5. The process of claim 4 , wherein the 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.

6. The process of claim 5 , 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%.

7. The process of claim 5 , 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.

8. The process of claim 7 , wherein said at least one carboxyl-containing vinylic monomer is acrylic acid, methacrylic acid, ethylacrylic acid, 2-(meth)acrylamidoglycolic acid, and combinations thereof.

9. The process of claim 7 , 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.

10. The process of claim 7 , 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 combinations thereof.

11. The process of claim 7 , wherein the lens bulk material is a silicone hydrogel material, wherein the silicone hydrogel bulk material comprises: (1) repeating units of at least one polysiloxane vinylic monomer; (2) repeating units of at least one hydrophilic vinylic monomer; (3) repeating units of at least one polysiloxane vinylic crosslinker; (4) repeating units of at least one hydrophilic N-vinyl amide monomer; (5) repeating units of at least one polycarbosiloxane vinylic monomer; (6) repeating units of at least one polycarbosiloxane vinylic crosslinker; (7) repeating units of at least one silicone-containing vinylic monomer having a bis(trialkylsilyloxy)alkylsilyl or tris(trialkylsilyloxy)silyl group; (8) repeating units of one or more blending vinylic monomers; (9) repeating units of one or more non-silicone vinylic crosslinking agents; or (10) combinations thereof.

12. The process of claim 7 , wherein the lens bulk material is a non-silicone hydrogel material, wherein the non-silicon hydrogel material comprises at least 50% by mole of repeating units of at least one hydroxyl-containing vinylic monomer.

13. A process for producing contact lenses, comprising the steps of:
(a) obtaining a contact lens precursor which is a coated contact lens and has a first polyquaternium-1 uptake (“PU o ”), wherein the coated contact lens comprises a lens bulk material completely covered with at least one layer of a polyanionic polymer, wherein the polyanionic polymer comprises at least 60% by mole of repeating units of at least one carboxyl-containing vinylic monomer; and
(b) heating the contact lens precursor in an aqueous solution in the presence of at least one polyaziridine to and at a temperature from about 30° C. to about 140° C. for a period of time sufficient to obtain the contact lens having a second polyquaternium-1 uptake (“PU pz ”), wherein the polyaziridine having a number average molecular weight of about 2000 Dalton or less and at least two aziridine groups each of which is a mono-valent radical of formula

in which R1 is hydrogen, methyl or ethyl, wherein (PU o -PU pz )/PU o is at least 60%.

14. The process of claim 13 , wherein said at least one polyaziridine is 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.

15. The process of claim 14 , wherein the aqueous solution comprises 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 combination

Assignees

• Novartis Ag
• Alcon Inc

Inventors

• Qiu Yongxing
• Pruitt John Dallas
• Samuel Newton T

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

• B05D1/18

  performed by dipping · CPC title

• B29D11/00125

  Auxiliary operations, e.g. removing oxygen from the mould, conveying moulds from a storage to the production line in an inert atmosphere · CPC title

• B29D11/00038

  Production of contact lenses · CPC title

• B05D3/02

  by baking {(B05D3/04 takes precedence)} · CPC title