# US 11,029,446 B2 · Method for producing MPS-compatible water gradient contact lenses

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- Number: US 11,029,446 B2
- Document ID: US11029446B2
- Status: Granted
- Kind: B2
- Application number: 16/204,664
- Filed: 2018-11-29
- Published: 2019-06-13
- Granted: 2021-06-08
- Earliest claimed: 2017-12-13
- Assignees: Alcon Inc.
- Applicants: Novartis AG
- Inventors: Yongxing Qiu; John Dallas Pruitt; Newton T. Samuel
- Web page: https://patentgrep.com/patent/US11029446B2

## CPC

- G02B 1/043: {Contact lenses}
- B05D 5/00: Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
- B29D 11/00038: {Production of contact lenses}
- B29D 11/00125: {Auxiliary operations, e.g. removing oxygen from the mould, conveying moulds from a storage to the production line in an inert atmosphere}
- B29D 11/00865: {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)}
- B65B 55/22: Immersing contents in protective liquids
- C08L 33/02: Homopolymers or copolymers of acids; Metal or ammonium salts thereof
- C08L 79/04: Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L 83/04: Polysiloxanes
- C09D 133/02: Homopolymers or copolymers of acids; Metal or ammonium salts thereof
- G02B 1/18: Coatings for keeping optical surfaces clean, e.g. hydrophobic or photo-catalytic films (G02B1/16 takes precedence)
- G02C 7/049: {Contact lenses having special fitting or structural features achieved by special materials or material structures}
- B05D 1/18: performed by dipping
- B05D 1/38: with intermediate treatment (intermediate treatment per se B05D3/00)
- B05D 3/002: {Pretreatement}
- B05D 3/02: by baking {(B05D3/04 takes precedence)}
- B05D 5/10: to obtain an adhesive surface
- B29K 2083/00: Use of polymers having silicon, with or without sulfur, nitrogen, oxygen, or carbon only, in the main chain, as moulding material
- B29K 2105/0061: {Gel or sol}
- C08L 2201/10: Transparent films; Clear coatings; Transparent materials
- C08L 2201/54: Aqueous solutions or dispersions
- G02B 2207/109: Sols, gels, sol-gel materials
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02)
- B29D: PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE (making granules B29B9/00; making preforms B29B11/00)
- B65B: MACHINES, APPARATUS OR DEVICES FOR, OR METHODS OF, PACKAGING ARTICLES OR MATERIALS; UNPACKING (bundling and pressing devices for cigars A24C1/44; devices for tensioning and securing binders adapted to be supported by the article or articles to be bound B25B25/00; applying closure members to bottles, jars or similar containers B67B1/00-B67B6/00; concurrent cleaning, filling and closing of bottles B67C7/00; emptying bottles, jars, cans, casks, barrels or similar containers B67C9/00)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- G02C: SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES (trial frames for testing the eyes A61B3/04; goggles or eyeshields not having the same features as spectacles A61F9/00)
- B29K: INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR {MOULDS, } REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS

## 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.

## Claims

### Claim 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 (“PUo”), 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 (“PUpz”), 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 (PUo-PUpz)/PUo is at least 60%.

### Claim 2 (depends on 1)

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.

### Claim 3 (depends on 2)

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, —[OC2H4O]n1—, —CONHR1, —CONR1—, and combinations thereof, wherein n1 is an integer of 1 to 10 and R1 is hydrogen, methyl or ethyl.

### Claim 4 (depends on 3)

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.

### Claim 5 (depends on 4)

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.

### Claim 6 (depends on 5)

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%.

### Claim 7 (depends on 5)

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.

### Claim 8 (depends on 7)

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.

### Claim 9 (depends on 7)

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.

### Claim 10 (depends on 7)

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.

### Claim 11 (depends on 7)

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.

### Claim 12 (depends on 7)

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.

### Claim 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 (“PUo”), 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 (“PUpz”), 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 (PUo-PUpz)/PUo is at least 60%.

### Claim 14 (depends on 13)

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.

### Claim 15 (depends on 14)

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, —[OC2H4O]n1—, —CONHR1, —CONR1—, and combinations thereof, wherein n1 is an integer of 1 to 10 and R1 is hydrogen, methyl or ethyl.

### Claim 16 (depends on 15)

The process of claim 15, wherein the aqueous solution comprises from about 0.01% to about 2.5% by weight of said at least one polyaziridine.

### Claim 17 (depends on 16)

The process of claim 16, 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.

### Claim 18 (depends on 17)

The process of claim 17, 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%.

### Claim 19 (depends on 17)

The process of claim 17, 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.

### Claim 20 (depends on 19)

The process of claim 19, wherein said at least one carboxyl-containing vinylic monomer is acrylic acid, methacrylic acid, ethylacrylic acid, 2-(meth)acrylamidoglycolic acid, and combinations thereof.

### Claim 21 (depends on 19)

The process of claim 19, 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.

### Claim 22 (depends on 19)

The process of claim 19, 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.

### Claim 23 (depends on 19)

The process of claim 19, 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.