Method for producing embedded or hybrid hydrogel contact lenses

Patent metadata

Field	Value
Publication number	US-11833770-B2
Application number	US-202117205148-A
Country	US
Kind code	B2
Filing date	Mar 18, 2021
Priority date	Mar 19, 2020
Publication date	Dec 5, 2023
Grant date	Dec 5, 2023

Abstract

The invention is generally related to a method for producing, in a relatively efficient and consistent manner, embedded or hybrid silicone hydrogel contact lenses, and also to unprocessed embedded or hybrid silicone hydrogel contact lenses, according to conventional cast-molding technologies. A method of the invention involve use of a polymeric non-reactive diluent in preparing a polymerizable composition for forming the silicone hydrogel material of the unprocessed embedded or hybrid silicone hydrogel contact lens, which is cast-molded with a lens mold. The unprocessed cast-molded embedded or hybrid silicone hydrogel contact lens has no or a minimal water-swelling degree, so that lens distortion or delamination during the hydration of the unprocessed embedded or hybrid silicone hydrogel contact lens.

First claim

What is claimed is:

1. A method for producing embedded silicone hydrogel contact lenses, wherein each of the embedded silicone hydrogel contact lenses has at least one insert embedded therein, comprising the steps of:
(1) obtaining a polymerizable composition for forming a silicone hydrogel material, wherein the polymerizable composition comprising from about 1% to about 25% by weight of at least one polymeric non-reactive diluent relative to the total weight of the polymerizable composition and polymerizable materials dissolved in or blended with the polymeric diluent, wherein the polymerizable materials comprise (a) at least one silicone-containing vinylic monomer and/or at least one silicone-containing vinylic crosslinker and (b) at least one hydrophilic vinylic monomer, wherein said at least one polymeric non-reactive diluent comprises a poly(C 2 -C 4 alkyleneoxide) polymer;
(2) obtaining a lens mold, wherein the lens mold comprises a male mold half having a first molding surface and a female mold half having a second molding surface, wherein the male and female mold halves are configured to receive each other such that a mold cavity is formed between the first and second molding surfaces when the mold is closed;
(3) obtaining an insert or a disk, wherein the insert is made of a non-hydrogel material;
(4) in no particular order, placing the insert at a specified position in the lens mold and introducing the polymerizable composition in the lens mold, wherein the insert is immersed in the polymerizable composition in the lens mold;
(5) curing the polymerizable composition in the lens mold to form an unprocessed embedded silicone hydrogel contact lens, wherein the unprocessed embedded silicone hydrogel contact lens has the insert surrounded by the silicone hydrogel material;
(6) separating the lens mold obtained in step (5) into the male and female mold halves, with the unprocessed embedded silicone hydrogel contact lens adhered on a lens-adhered mold half which is one of the male and female mold halves;
(7) removing the unprocessed embedded silicone hydrogel contact lens from the lens-adhered mold half; and
(8) subjecting the unprocessed embedded silicone hydrogel contact lens to post-molding processes including a hydration process and one or more other processes selected from the group consisting of extraction, surface treatment, packaging, sterilization, and combinations thereof to obtain the embedded silicone hydrogel contact lenses.

2. The method of claim 1 , wherein the unprocessed embedded silicone hydrogel contact lens is mechanically removed from the lens-adhered mold half.

3. The method of claim 2 , wherein the step of removing the unprocessed embedded silicone hydrogel contact lens from the lens-adhered mold half is aided by blowing cold air over the unprocessed embedded silicone hydrogel contact lens and/or the lens-adhered mold half.

4. The method of claim 1 , wherein the step of curing the polymerizable composition in the lens mold is carried out actinically by irradiating the polymerizable composition in the mold with a UV light or visible light.

5. The method of claim 1 , wherein the step of curing the polymerizable composition in the lens mold is carried out thermally in an oven at a temperature of from 25° C. to 120° C. for from about 1 to 24 hours.

6. The method of claim 5 , wherein the step of curing is carried out under an inert atmosphere.

7. The method of claim 1 , wherein the amount of the polymeric non-reactive diluent in the polymerizable composition is sufficient for providing the unprocessed embedded silicone hydrogel contact lens with a water-swelling degree of from about −7% to about 7%.

8. The method of claim 7 , wherein the polymerizable composition comprises less than 10% by weight of any non-reactive diluent other than the polymeric non-reactive diluent.

9. The method of claim 8 , wherein the polymerizable composition comprises: (i) from about 20% to about 79% by weight of said at least one silicone-containing vinylic monomer and/or said at least one silicone-containing vinylic crosslinker relative to the total weight of the polymerizable composition; (ii) from 20% to about 79% by weight of the hydrophilic vinylic monomer relative to the total weight of the polymerizable composition; (iii) from 0 to about 2.5 by weight of at least one non-silicone vinylic crosslinker relative to the total weight of the polymerizable composition; (iv) from 0 to about 15% by weight of at least one blending vinylic monomer relative to the total weight of the polymerizable composition; or (vi) combinations thereof.

10. The method of claim 9 , wherein the sum of the amounts of polymerizable materials (a) and (b) is at least 70% by weight relative to the total amount of all polymerizable materials in the polymerizable composition.

11. The method of claim 10 , wherein at least one poly(C 2 -C 4 alkyleneoxide) polymer is represented by formula of R 1 —O-(EO) m1 (PO) n1 (BO) p1 —R 2 in which: R 1 and R 2 independent of each other is hydrogen or a C 1 -C 4 alkyl; EO is a divalent radical of ethyleneoxide (—CH 2 —CH 2 —O—); PO is a divalent radical of propyleneoxide

 BO is a divalent radical of butyleneoxide

 m1 is zero or an integer of from 5 to 65; n1 is zero or an integer of from 5 to 52; p1 is zero or integer of from 5 to 30; wherein if n1 is not zero, p1 is zero; wherein if p1 is not zero, n1 is zero and m1 is not zero; wherein (m1+n1+p1) is a value to provide the poly(C 2 -C 4 alkyleneoxide) polymer with a number average molecular weight of from about 300 to about 3000 Daltons.

12. The method of claim 11 , wherein at least one poly(C 2 -C 4 alkyleneoxide) polymer is poly(ethyleneoxide) (“PEO”), poly(propyleneoxide) (“PPO”), poly(ethyleneoxide)-poly(propyleneoxide) di-block copolymer (“PEO-PPO”), poly(ethyleneoxide)-poly(propyleneoxide)-poly(ethyleneoxide) tri-block copolymer (“PEO-PPO-PEO”), poly(propyleneoxide)-poly(ethyleneoxide)-poly(propyleneoxide) tri-block copolymer (“PPO-PEO-PPO”), poly(ethyleneoxide)-poly(butyleneoxide) di-block copolymer (“PEO-PBO”), poly(ethyleneoxide)-poly(butyleneoxide)-poly(ethyleneoxide) tri-block copolymer (“PEO-PBO-PEO”), poly(butyleneoxide)-poly(ethyleneoxide)-poly(butyleneoxide) tri-block copolymer (“PBO-PEO-PBO”), or a mixture thereof.

13. The method of claim 11 , wherein at least one poly(C 2 -C 4 alkyleneoxide) polymer is poly(propyleneoxide) (“PPO”).

14. The method of claim 11 , wherein said at least one silicone-containing vinylic monomer is a vinylic monomer having a bis(trialkylsilyloxy)alkylsilyl group or a tris(trialkylsilyloxy)silyl group, a polysiloxane vinylic monomer, a polycarbosiloxane vinylic monomer, 3-methacryloxy propylpentamethyldisiloxane, t-butyldimethyl-siloxyethyl vinyl carbonate, trimethylsilylethyl vinyl carbonate, trimethylsilylmethyl vinyl carbonate, or combinations thereof, wherein said at least one silicone-containing vinylic monomer is a polysiloxane vinylic crosslinkers, a polycarbosiloxane vinylic crosslinker, or combinations thereof; wherein said at least one hydrophilic vinylic monomer comprises an alkyl (meth)acrylamide, a hydroxyl-containing acrylic monomer, an amino-containing acrylic monomer, a carboxyl-containing acrylic monomer, a N-vinyl amide monomer, a methylene-containing pyrrolidone monomer, an acrylic monomer having a C 1 -C 4 alkoxyethoxy group, a vinyl ether monomer, an allyl ether monomer, a phosphorylcholine-containing

Assignees

• Alcon Inc

Inventors

• Zheng Yang
• Ge Junhao
• Zhang Steve Yun

Classifications

• B29D11/00038 Primary

  Production of contact lenses · CPC title

• C08J3/075

  Macromolecular gels · CPC title

• C08J3/24

  Crosslinking, e.g. vulcanising, of macromolecules (mechanical aspects B29C35/00; crosslinking agents C08K) · CPC title

• C08L83/04

  Polysiloxanes · CPC title

• G02B1/043

  Contact lenses · CPC title