CA2456036A1 - Method for coating articles by mold transfer - Google Patents

Method for coating articles by mold transfer Download PDF

Info

Publication number
CA2456036A1
CA2456036A1 CA002456036A CA2456036A CA2456036A1 CA 2456036 A1 CA2456036 A1 CA 2456036A1 CA 002456036 A CA002456036 A CA 002456036A CA 2456036 A CA2456036 A CA 2456036A CA 2456036 A1 CA2456036 A1 CA 2456036A1
Authority
CA
Canada
Prior art keywords
coating
coating composition
poly
contact lens
amount
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002456036A
Other languages
French (fr)
Other versions
CA2456036C (en
Inventor
David C. Turner
Lenora C. Copper
Dominic Gourd
Shivkumar Mahadevan
Frank F. Molock
Kevin P. Mccabe
Dharmesh K. Dubey
Jeffrey S. Longo
Jonathan P. Adams
Andrew J. Wagner
Xiaoping Lin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Johnson and Johnson Vision Care Inc
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2456036A1 publication Critical patent/CA2456036A1/en
Application granted granted Critical
Publication of CA2456036C publication Critical patent/CA2456036C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C37/00—Component parts, details, accessories or auxiliary operations, not covered by group B29C33/00 or B29C35/00
    • B29C37/0025—Applying surface layers, e.g. coatings, decorative layers, printed layers, to articles during shaping, e.g. in-mould printing
    • B29C37/0028—In-mould coating, e.g. by introducing the coating material into the mould after forming the article
    • B29C37/0032—In-mould coating, e.g. by introducing the coating material into the mould after forming the article the coating being applied upon the mould surface before introducing the moulding compound, e.g. applying a gelcoat
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C39/00—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor
    • B29C39/02—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor for making articles of definite length, i.e. discrete articles
    • B29C39/04—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor for making articles of definite length, i.e. discrete articles using movable moulds not applied
    • B29C39/08—Introducing the material into the mould by centrifugal force
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
    • B29D11/00—Producing optical elements, e.g. lenses or prisms
    • B29D11/00009—Production of simple or compound lenses
    • B29D11/00038—Production of contact lenses
    • B29D11/00125—Auxiliary operations, e.g. removing oxygen from the mould, conveying moulds from a storage to the production line in an inert atmosphere
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
    • B29D11/00—Producing optical elements, e.g. lenses or prisms
    • B29D11/00009—Production of simple or compound lenses
    • B29D11/00471—Production of simple or compound lenses made by rotational casting
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • 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
    • B29K2105/00—Condition, form or state of moulded material or of the material to be shaped
    • B29K2105/0002—Condition, form or state of moulded material or of the material to be shaped monomers or prepolymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • 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
    • B29K2995/00—Properties of moulding materials, reinforcements, fillers, preformed parts or moulds
    • B29K2995/0037—Other properties
    • B29K2995/0092—Other properties hydrophilic
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29L—INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
    • B29L2011/00—Optical elements, e.g. lenses, prisms
    • B29L2011/0016—Lenses
    • B29L2011/0041—Contact lenses

Abstract

A method for coating hydrogel and silicone hydrogel articles, and articles made by the method, are provided in which the coating is first applied to th e molding surface in which an article-forming material will be cured to form t he article. The method permits the thickness and uniformity of the coating to b e more easily controlled than in known coating methods.

Claims (51)

1. ~A method for manufacturing an article comprising the steps of a.) coating a molding surface of a mold or a mold half with a coating effective amount of a high molecular weight coating composition; b.) dispensing a mixture comprising a hydrogel monomer, a silicone-containing hydrogel monomer, or a combination thereof into the mold or mold half; and c.) curing the monomer mixture and the coating composition using a dwell time of less than about 5 minutes and under conditions suitable to form an article coated with the coating composition.
2. ~The method of claim 1, wherein the article is a contact lens.
3. ~The method of claim 1 or 2, wherein the monomer mixture comprises a hydrogel.
4. ~The method of claim 1 or 2, wherein the monomer mixture comprises a silicone hydrogel monomer.
5. ~The method of claim 1, wherein the molecular weight of the coating composition is greater than about 300 kD.
6. ~The method of claim 1, wherein the dwell time is less than about 45 seconds.
7. ~The method of claim 5, wherein the dwell time is less than about 45 seconds.
8. ~The method of claim 1, wherein the coating composition further comprises a low boiling point solvent and a high boiling point solvent.

36~
9. The method of claim 8, wherein the coating of the molding surface is carried out by spin coating.
10. The method of claim 9, wherein spin coating is carried out using at least about 2 µl and no more than about 20 µl of the coating composition.
11. The method of claim 10, further comprising applying, subsequent to the spin coating step, a pressurized air jet to an edge of the mold.
12. An article formed by the method of claim 1, 6, 7, or 9.
13. A contact lens formed by the method of claim 2.
14. A method for manufacturing an article comprising: a.) coating a molding surface of a mold or a mold half with a coating effective amount of a high molecular weight hydrophilic coating composition; b.) dispensing a mixture of a hydrogel monomer, silicone-containing hydrogel monomer, or combination thereof into the mold or mold half; and c.) curing the monomer mixture and coating composition using a dwell time of less than about 5 minutes and under conditions suitable to form an article coated with the coating composition.
15. The method of claim 14, wherein the article is a contact lens.
16. The method of claim 15, wherein the monomer mixture comprises a hydrogel monomer.
17. The method of claim 15, wherein the monomer mixture comprises a silicone hydrogel monomer.
18. ~The method of claim 14, wherein the dwell time is less than about 45 seconds.
19. ~The method of claim 17, wherein the silicone hydrogel monomer mixture comprises a reaction product of a silicone based macromer Group Transfer Polymerization product and a polymerizable mixture comprising Si8-10 monomethacryloxy terminated polydimethyl siloxane, polydimethylsiloxane other than Si8-10 monomethacryloxy terminated polydimethyl siloxane, and a hydrophilic monomer.
20. The method of claim 19, wherein the silicone hydrogel monomer mixture comprises the macromer in an amount of about 15 to about 25 wt percent, the Si8-10 monomethacryloxy terminated polydimethyl siloxane in an amount of about 20 to about 30 wt percent; methacryloxypropyl tris(trimethyl siloxy) silane in an amount of about 15 to about 25 wt percent;
N,N-dimethyl acrylamide in an amount of about 20 to about 30 wt percent; 2-hydroxy ethyl methacrylate in an amount of about 2 to about 7 wt percent;
tetraethyleneglycol dimethacrylate in an amount of about 0 to about 5 wt percent and poly(N-vinyl pyrrolidinone) in an amount of about 0 to about 5 weight percent.
21. The method of claim 14, 15, 16, 17, 18, 19, or 20 wherein the coating composition comprises polyvinyl alcohol), polyethylene oxide, poly(2-hydroxyethyl methacrylate), poly(acrylic acid), poly(methacrylic acid), poly(maleic acid), poly(itaconic acid), poly(acrylamide), poly(dimethylacrylamide), carboxymethylated polymers, polystyrene sulfonic acid, polysulfonate polymers, polysaccharides, glucose amino glycans, block or random copolymers thereof, or mixtures thereof.
22. The method of claim 21, wherein the coating composition comprises poly(2-hydroxyethyl methacrylate).
23. ~The method of claim 15, wherein the coating composition further comprises a low boiling point solvent and a high boiling point solvent.
24. ~The method of claim 23, wherein the coating of the molding surface is carried out by spin coating.
25. ~The method of claim 24, wherein spin coating is carried out using at least about 2 µl and no more than about 20 µl of the coating composition.
26. ~The method of claim 25, further comprising applying, subsequent to the spin coating step, a pressurized air jet to an edge of the mold.
27. ~An article formed by the method of claim 14.
28. ~A contact lens formed by the method of claim 15, 18, 19, or 20.
29. ~A contact lens formed by the method of claim 21.
30. ~A contact lens formed by the method of claim 22.
31. ~A method for manufacturing contact lenses comprising: a.) coating a molding surface of a mold or a mold half with a coating effective amount of a hydrophilic coating composition having a molecular weight of greater than about 300 kD; b.) dispensing a mixture comprising a hydrogel monomer, a silicone-containing hydrogel monomer, or a combination thereof into the mold or mold half; and c.) curing the monomer mixture and coating composition using a dwell time of less than about 45 seconds and under conditions suitable to form a contact lens coated with the coating composition, wherein the formed lens exhibits physiological compatibility.
32. ~The method of claim 31, wherein the monomer mixture comprises hydrogel monomer.
33. ~The method of claim 31, wherein the monomer mixture comprises silicone hydrogel monomer.
34. ~The method of claim 33, wherein the silicone hydrogel monomer mixture comprises a reaction product of a silicone based macromer Group Transfer Polymerization product and a polymerizable mixture comprising Si8-10 monomethacryloxy terminated polydimethyl siloxane, polydimethylsiloxane other than Si8-10 monomethacryloxy terminated polydimethyl siloxane, and a hydrophilic monomer.
35. ~The method of claim 34, wherein the silicone hydrogel monomer mixture comprises the macromer an amount of about 15 to about 25 wt percent, the Si8-10 monomethacryloxy terminated polydimethyl siloxane in an amount of about 20 to about 30 wt percent; methacryloxypropyl tris(trimethyl siloxy) silane in an amount of about 15 to about 25 wt percent;
N,N-dimethyl acrylamide in an amount of about 20 to about 30 wt percent; 2-hydroxy ethyl methacrylate in an amount of about 2 to about 7 wt percent;
tetraethyleneglycol dimethacrylate in an amount of about 0 to about 5 wt percent and poly(N-vinyl pyrrolidinone) in an amount of about 0 to about 5 weight percent.
36. ~The method of claim 31, 32, 33, 34, or 35, wherein the coating composition comprises poly(vinyl alcohol), polyethylene oxide, poly(2-hydroxyethyl methacrylate), poly(acrylic acid), poly(methacrylic acid), poly(maleic acid), poly(itaconic acid), poly(acrylamide), poly(dimethacrylamide), carboxymethylated polymers, polystyrene sulfonic acid, polysulfonate polymers, polysaccharides, glucose amino glycans, block or random copolymers thereof, or mixtures thereof.
37. The method of claim 36, wherein the coating composition comprises poly(2-hydroxyethyl methacrylate).
38. The method of claim 36, wherein the coating composition further comprises a low boiling point solvent and a high boiling point solvent.
39. The method of claim 38, wherein the coating of the molding surface is carried out by spin coating.
40. The method of claim 39, wherein spin coating is carried out using at least about 2 µl and no more than about 20 µl of the coating composition.
41. The method of claim 40, further comprising applying, subsequent to the spin coating step, a pressurized air jet to an edge of the mold.
42. A contact lens formed by the method of claim 31, 32, 33, 34, or 35.
43. A contact lens formed by the method of claim 36.
44. A contact lens formed by the method of claim 37.
45. A contact lens formed by the method of claim 38.
46. A contact lens formed by the method of claim 39.
47. The contact lens of claim 42, wherein the coating composition comprises a coating of a dry film thickness of not less than about 5 nm and not more than about 70 nm.
48. The contact lens of claim 43, wherein the coating composition comprises a coating of a dry film thickness of not less than about 5 nm and not more than about 70 nm.
49. The contact lens of claim 44, wherein the coating composition comprises a coating of a dry film thickness of not less than about 5 nm and not more than about 70 nm.
50. The contact lens of claim 45, wherein the coating composition comprises a coating of a dry film thickness of not less than about 5 nm and not more than about 70 nm.
51. The contact lens of claim 4, wherein the coating composition comprises a coating of a dry film thickness of not less than about 5 nm and not more than about 70 nm.
CA2456036A 2001-08-02 2002-07-29 Method for coating articles by mold transfer Expired - Fee Related CA2456036C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/921,192 US7879267B2 (en) 2001-08-02 2001-08-02 Method for coating articles by mold transfer
US09/921,192 2001-08-02
PCT/US2002/024022 WO2003011551A1 (en) 2001-08-02 2002-07-29 Method for in mold coating hydrogel articles

Publications (2)

Publication Number Publication Date
CA2456036A1 true CA2456036A1 (en) 2003-02-13
CA2456036C CA2456036C (en) 2010-09-21

Family

ID=25445062

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2456036A Expired - Fee Related CA2456036C (en) 2001-08-02 2002-07-29 Method for coating articles by mold transfer

Country Status (13)

Country Link
US (1) US7879267B2 (en)
EP (1) EP1412154B1 (en)
JP (1) JP4387189B2 (en)
KR (1) KR100886580B1 (en)
CN (1) CN1289277C (en)
AR (1) AR035263A1 (en)
AU (1) AU2002322750B2 (en)
BR (1) BR0211644B1 (en)
CA (1) CA2456036C (en)
DE (1) DE60219318T2 (en)
HK (1) HK1063611A1 (en)
TW (1) TW590868B (en)
WO (1) WO2003011551A1 (en)

Families Citing this family (108)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6451871B1 (en) * 1998-11-25 2002-09-17 Novartis Ag Methods of modifying surface characteristics
US6822016B2 (en) 2001-09-10 2004-11-23 Johnson & Johnson Vision Care, Inc. Biomedical devices containing internal wetting agents
US20070043140A1 (en) * 1998-03-02 2007-02-22 Lorenz Kathrine O Method for the mitigation of symptoms of contact lens related dry eye
US7052131B2 (en) * 2001-09-10 2006-05-30 J&J Vision Care, Inc. Biomedical devices containing internal wetting agents
US7461937B2 (en) * 2001-09-10 2008-12-09 Johnson & Johnson Vision Care, Inc. Soft contact lenses displaying superior on-eye comfort
CA2422782C (en) 2000-10-19 2012-02-07 Applied Medical Resources Corporation Surgical access apparatus and method
CA2457687C (en) 2001-08-14 2013-01-15 Applied Medical Resources Corporation Access sealing apparatus and method
US20120245248A1 (en) * 2001-09-10 2012-09-27 Azaam Alli Silicone hydrogels formed from reaction mixtures free of hydrophilic monomers
TWI255224B (en) * 2002-01-09 2006-05-21 Novartis Ag Polymeric articles having a lubricious coating and method for making the same
EP2340791B1 (en) 2002-06-05 2012-11-14 Applied Medical Resources Corporation Wound retractor
US6936641B2 (en) * 2002-06-25 2005-08-30 Johnson & Johnson Vision Care, Inc. Macromer forming catalysts
KR101021433B1 (en) * 2002-08-16 2011-03-15 존슨 앤드 존슨 비젼 케어, 인코포레이티드 A mold for producing contact lenses, a method of making a lens, a lens, and a method for making a coated lenses
US8158695B2 (en) * 2002-09-06 2012-04-17 Johnson & Johnson Vision Care, Inc. Forming clear, wettable silicone hydrogel articles without surface treatments
US20070138692A1 (en) * 2002-09-06 2007-06-21 Ford James D Process for forming clear, wettable silicone hydrogel articles
US20040150788A1 (en) 2002-11-22 2004-08-05 Ann-Margret Andersson Antimicrobial lenses, processes to prepare them and methods of their use
US6926965B2 (en) * 2002-09-11 2005-08-09 Novartis Ag LbL-coated medical device and method for making the same
JP4776926B2 (en) * 2002-12-23 2011-09-21 ジョンソン・アンド・ジョンソン・ビジョン・ケア・インコーポレイテッド Contact lens package with additives
US20050020884A1 (en) 2003-02-25 2005-01-27 Hart Charles C. Surgical access system
CA2518108C (en) * 2003-03-07 2014-07-08 Johnson & Johnson Vision Care, Inc. Diluents for forming clear, wettable silicone hydrogel articles
WO2005013803A2 (en) * 2003-08-06 2005-02-17 Applied Medical Resources Corporation Surgical device with tack-free gel and method of manufacture
AU2004286869A1 (en) * 2003-11-05 2005-05-19 Johnson & Johnson Vision Care, Inc. Methods of inhibiting the adherence of lenses to their packaging materials
US7416737B2 (en) 2003-11-18 2008-08-26 Johnson & Johnson Vision Care, Inc. Antimicrobial lenses, processes to prepare them and methods of their use
US7805822B2 (en) * 2003-12-15 2010-10-05 Turbocombustor Technology, Inc. Process for removing thermal barrier coatings
US7786185B2 (en) 2004-03-05 2010-08-31 Johnson & Johnson Vision Care, Inc. Wettable hydrogels comprising acyclic polyamides
EP1805013A1 (en) * 2004-10-29 2007-07-11 3M Innovative Properties Company Optical films incorporating cyclic olefin copolymers
US7572468B1 (en) * 2004-12-28 2009-08-11 The United States Of America As Represented By The Secretary Of Agriculture Extraction of carotenoids from plant material
US7799249B2 (en) * 2005-08-09 2010-09-21 Coopervision International Holding Company, Lp Systems and methods for producing silicone hydrogel contact lenses
US20070037897A1 (en) * 2005-08-12 2007-02-15 Guigui Wang Method for making contact lenses
AU2006301984A1 (en) 2005-10-14 2007-04-19 Applied Medical Resources Corporation Method of making a hand access laparoscopic device
US20070087113A1 (en) * 2005-10-19 2007-04-19 Bausch & Lomb Incorporated Surface-modified medical devices and method of making
TWI351415B (en) * 2006-02-08 2011-11-01 Johnson & Johnson Vision Care Facilitating release of silicone hydrogel ophthalm
AU2011203208B2 (en) * 2006-02-08 2014-12-04 Johnson & Johnson Vision Care, Inc. Facilitating release of silicone hydrogel ophthalmic lenses
US20070222095A1 (en) * 2006-03-23 2007-09-27 Diana Zanini Process for making ophthalmic lenses
US8414804B2 (en) * 2006-03-23 2013-04-09 Johnson & Johnson Vision Care, Inc. Process for making ophthalmic lenses
US8044112B2 (en) * 2006-03-30 2011-10-25 Novartis Ag Method for applying a coating onto a silicone hydrogel lens
US7858000B2 (en) * 2006-06-08 2010-12-28 Novartis Ag Method of making silicone hydrogel contact lenses
TWI512017B (en) * 2006-06-15 2015-12-11 Coopervision Int Holding Co Lp Wettable silicone hydrogel contact lenses and related compositions and methods
WO2007147152A2 (en) * 2006-06-15 2007-12-21 Lai Shui T High visual acuity contact lenses
US8231218B2 (en) 2006-06-15 2012-07-31 Coopervision International Holding Company, Lp Wettable silicone hydrogel contact lenses and related compositions and methods
US7960465B2 (en) * 2006-06-30 2011-06-14 Johnson & Johnson Vision Care, Inc. Antimicrobial lenses, processes to prepare them and methods of their use
WO2008008752A2 (en) 2006-07-12 2008-01-17 Novartis Ag Actinically crosslinkable copolymers for manufacturing contact lenses
EP3015119A1 (en) * 2006-10-30 2016-05-04 Novartis AG Method for applying a coating onto a silicone hydrogel lens
US7968650B2 (en) * 2006-10-31 2011-06-28 Johnson & Johnson Vision Care, Inc. Polymeric compositions comprising at least one volume excluding polymer
AR064286A1 (en) 2006-12-13 2009-03-25 Quiceno Gomez Alexandra Lorena PRODUCTION OF OPHTHALMIC DEVICES BASED ON POLYMERIZATION BY PHOTOINDUCIDED SCALE GROWTH
WO2008074838A1 (en) * 2006-12-21 2008-06-26 Novartis Ag Process for the coating of biomedical articles
CA2682923C (en) 2007-05-11 2014-10-07 Applied Medical Resources Corporation Surgical retractor with gel pad
TWI551305B (en) * 2007-08-31 2016-10-01 諾華公司 Use of a relatively-viscous packaging solution
US8689971B2 (en) * 2007-08-31 2014-04-08 Novartis Ag Contact lens packaging solutions
US20090200692A1 (en) * 2008-02-07 2009-08-13 Jame Chang Method for manufacturing a silicone contact lens having a hydrophilic surface
MY152305A (en) * 2008-03-18 2014-09-15 Novartis Ag Coating process for ophthalmic lenses
CA2730506A1 (en) * 2008-07-21 2010-01-28 Novartis Ag Silicone-containing polymeric materials with hydrolyzable groups
US8128951B2 (en) 2008-09-15 2012-03-06 Cv Ingenuity Corp. Local delivery of water-soluble or water-insoluble therapeutic agents to the surface of body lumens
US8114429B2 (en) * 2008-09-15 2012-02-14 Cv Ingenuity Corp. Local delivery of water-soluble or water-insoluble therapeutic agents to the surface of body lumens
US8257722B2 (en) 2008-09-15 2012-09-04 Cv Ingenuity Corp. Local delivery of water-soluble or water-insoluble therapeutic agents to the surface of body lumens
US9198968B2 (en) 2008-09-15 2015-12-01 The Spectranetics Corporation Local delivery of water-soluble or water-insoluble therapeutic agents to the surface of body lumens
US20130203812A1 (en) 2008-09-30 2013-08-08 Johnson & Johnson Vision Care, Inc. Ionic silicone hydrogels comprising pharmaceutical and/or nutriceutical components and having improved hydrolytic stability
US8470906B2 (en) * 2008-09-30 2013-06-25 Johnson & Johnson Vision Care, Inc. Ionic silicone hydrogels having improved hydrolytic stability
JP5671468B2 (en) 2008-10-13 2015-02-18 アプライド メディカル リソーシーズ コーポレイション Single port access system
US8927618B2 (en) * 2009-11-18 2015-01-06 Menicon Co., Ltd. Dye composition for ophthalmic lens, method for producing colored ophthalmic lens using the same, and colored ophthalmic lens
US8877103B2 (en) 2010-04-13 2014-11-04 Johnson & Johnson Vision Care, Inc. Process for manufacture of a thermochromic contact lens material
US9690115B2 (en) 2010-04-13 2017-06-27 Johnson & Johnson Vision Care, Inc. Contact lenses displaying reduced indoor glare
US8697770B2 (en) 2010-04-13 2014-04-15 Johnson & Johnson Vision Care, Inc. Pupil-only photochromic contact lenses displaying desirable optics and comfort
JP5956438B2 (en) 2010-07-09 2016-07-27 クーパーヴィジョン インターナショナル ホウルディング カンパニー リミテッド パートナーシップ Polar thermoplastic ophthalmic lens mold, ophthalmic lens molded therein, and related methods
WO2012016152A1 (en) 2010-07-30 2012-02-02 Siddiqui A K M Shahab Ophthalmic lens molds, ophthalmic lenses molded therein, and related methods
KR102139022B1 (en) * 2010-07-30 2020-07-29 알콘 인코포레이티드 A silicone hydrogel lens with a crosslinked hydrophilic coating
JP6396657B2 (en) 2010-10-01 2018-09-26 アプライド メディカル リソーシーズ コーポレイション Natural orifice surgery system
US9289115B2 (en) 2010-10-01 2016-03-22 Applied Medical Resources Corporation Natural orifice surgery system
US9623614B2 (en) 2010-11-10 2017-04-18 Novartis Ag Method for making contact lenses
KR20200006622A (en) 2011-05-10 2020-01-20 어플라이드 메디컬 리소시스 코포레이션 Wound retractor
WO2012170603A1 (en) * 2011-06-09 2012-12-13 Novartis Ag Silicone hydrogel lenses with nano-textured surfaces
JP5863008B2 (en) * 2011-09-12 2016-02-16 国立研究開発法人理化学研究所 Polymer in which dissimilar materials are joined, and method for producing the same
HUE029018T2 (en) 2011-10-12 2017-02-28 Novartis Ag Method for making uv-absorbing ophthalmic lenses by coating
HUE043061T2 (en) * 2011-10-28 2019-07-29 Novartis Ag Method for molding an ophthalmic lens and device for applying a coating to the surface of an ophthalmic lens mold
US9956385B2 (en) 2012-06-28 2018-05-01 The Spectranetics Corporation Post-processing of a medical device to control morphology and mechanical properties
US9395468B2 (en) 2012-08-27 2016-07-19 Ocular Dynamics, Llc Contact lens with a hydrophilic layer
WO2014095690A1 (en) 2012-12-17 2014-06-26 Novartis Ag Method for making improved uv-absorbing ophthalmic lenses
EP2967512B1 (en) 2013-03-15 2019-11-06 Applied Medical Resources Corporation Mechanical gel surgical access device
CA2930552C (en) 2013-11-15 2022-12-13 Ocular Dynamics, Llc Contact lens with a hydrophilic layer
US9708087B2 (en) 2013-12-17 2017-07-18 Novartis Ag Silicone hydrogel lens with a crosslinked hydrophilic coating
US10525171B2 (en) 2014-01-24 2020-01-07 The Spectranetics Corporation Coatings for medical devices
ES2703184T3 (en) 2014-07-18 2019-03-07 Applied Med Resources Method for manufacturing gels that have permanent tack-free coatings
ES2731049T3 (en) 2014-08-15 2019-11-13 Applied Med Resources Natural hole surgery system
CN106715101B (en) 2014-08-26 2019-11-05 诺华股份有限公司 Method for applying stable coating in silicone hydrogel contact lens on piece
US10562248B2 (en) 2014-09-04 2020-02-18 Essilor International Optical lens comprising a protective removable film
WO2016085930A2 (en) 2014-11-25 2016-06-02 Applied Medical Resources Corporation Circumferential wound retraction with support and guidance structures
US9789654B2 (en) 2014-12-05 2017-10-17 Coopervision International Holding Company, Lp Method of manufacturing wettable silicone hydrogel contact lenses
CN107206119B (en) 2014-12-09 2021-01-29 实体科学公司 Medical device coating with biocompatible layer
EP3349675B1 (en) 2015-09-15 2020-10-21 Applied Medical Resources Corporation Surgical robotic access system
ES2951168T3 (en) 2015-10-07 2023-10-18 Applied Med Resources Multi-segment outer ring wound retractor
EP3543004B1 (en) 2015-12-03 2020-08-26 Alcon Inc. Contact lens packaging solutions
EP3391101B1 (en) 2015-12-15 2020-07-08 Alcon Inc. Method for applying stable coating on silicone hydrogel contact lenses
US10371865B2 (en) * 2016-07-06 2019-08-06 Johnson & Johnson Vision Care, Inc. Silicone hydrogels comprising polyamides
US10370476B2 (en) * 2016-07-06 2019-08-06 Johnson & Johnson Vision Care, Inc. Silicone hydrogels comprising high levels of polyamides
US10422927B2 (en) 2016-07-14 2019-09-24 Coopervision International Holding Company, Lp Method of manufacturing silicone hydrogel contact lenses having reduced rates of evaporation
AU2017324450B2 (en) 2016-09-12 2022-09-29 Applied Medical Resources Corporation Surgical robotic access system for irregularly shaped robotic actuators and associated robotic surgical instruments
US10676575B2 (en) * 2016-10-06 2020-06-09 Johnson & Johnson Vision Care, Inc. Tri-block prepolymers and their use in silicone hydrogels
JP6930534B2 (en) * 2017-05-11 2021-09-01 東レ株式会社 Manufacturing method of medical device
US20180354213A1 (en) 2017-06-13 2018-12-13 Coopervision International Holding Company, Lp Method of Manufacturing Coated Silicone Hydrogel Contact Lenses
CN107486537B (en) * 2017-06-27 2019-10-25 马鞍山市鑫龙特钢有限公司 A kind of preparation method of smokeless casting mold-releasing agent
CN111386478B (en) 2017-12-13 2023-11-14 爱尔康公司 Zhou Pao and month polishing gradient contact lens
JP6850268B2 (en) * 2018-02-09 2021-03-31 信越化学工業株式会社 (Meta) Acrylic Silicone Graft Copolymer and Its Manufacturing Method
US10996491B2 (en) 2018-03-23 2021-05-04 Johnson & Johnson Vision Care, Inc. Ink composition for cosmetic contact lenses
SG11202007012TA (en) 2018-03-28 2020-10-29 Alcon Inc Method for making silicone hydrogel contact lenses
DE102018127812B4 (en) 2018-11-07 2020-06-18 Fachhochschule Kiel Contact lens with a surface coating and manufacturing process
US11724471B2 (en) 2019-03-28 2023-08-15 Johnson & Johnson Vision Care, Inc. Methods for the manufacture of photoabsorbing contact lenses and photoabsorbing contact lenses produced thereby
US11578176B2 (en) 2019-06-24 2023-02-14 Johnson & Johnson Vision Care, Inc. Silicone hydrogel contact lenses having non-uniform morphology
US11891526B2 (en) 2019-09-12 2024-02-06 Johnson & Johnson Vision Care, Inc. Ink composition for cosmetic contact lenses
CN113021738B (en) * 2019-12-24 2023-06-27 烟台爱博诺德医用材料有限公司 Process for the preparation of ophthalmic materials

Family Cites Families (70)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3926756A (en) 1968-12-06 1975-12-16 Hercules Inc Process for preparing high molecular-weight, water soluble vinyl polymers by irradiation
US3912607A (en) 1969-10-22 1975-10-14 Rhone Progil Process for obtaining high molecular weight water-soluble acrylic polymers and copolymers using radiation
US3968305A (en) 1970-12-28 1976-07-06 Mitsubishi Rayon Co., Ltd. Mar-resistant synthetic resin shaped article
US3916033A (en) 1971-06-09 1975-10-28 High Voltage Engineering Corp Contact lens
US3764502A (en) 1971-08-12 1973-10-09 Ici America Inc Water soluble sodium acrylate polymers of high molecular weight
US4115339A (en) 1971-11-18 1978-09-19 Hercules Incorporated High molecular-weight, water-soluble vinyl polymers
US3808178A (en) 1972-06-16 1974-04-30 Polycon Laboratories Oxygen-permeable contact lens composition,methods and article of manufacture
US3948740A (en) 1973-05-04 1976-04-06 Hercules Incorporated Polymerization of water soluble monomers with radiation and chemical initiator
US4099859A (en) 1974-12-02 1978-07-11 High Voltage Engineering Corporation Contact lens having a smooth surface layer of a hydrophilic polymer
JPS5539170B2 (en) 1975-01-16 1980-10-08
FR2348227A1 (en) 1976-04-14 1977-11-10 Rhone Poulenc Ind IMPROVEMENT IN PROCESSES FOR THE PREPARATION OF WATER-SOLUBLE ACRYLIC POLYMERS BY PHOTOPOLYMERIZATION
US4120570A (en) 1976-06-22 1978-10-17 Syntex (U.S.A.) Inc. Method for correcting visual defects, compositions and articles of manufacture useful therein
US4136250A (en) 1977-07-20 1979-01-23 Ciba-Geigy Corporation Polysiloxane hydrogels
US4153641A (en) 1977-07-25 1979-05-08 Bausch & Lomb Incorporated Polysiloxane composition and contact lens
FR2431876A2 (en) 1978-07-24 1980-02-22 Rhone Poulenc Ind PROCESS FOR THE PREPARATION OF AQUEOUS SOLUTIONS OF OLEFINIC MONOMERS FOR PHOTOPOLYMERIZATION
US4190277A (en) 1978-08-30 1980-02-26 England Robert C Device for insertion, manipulation and removal of soft contact lenses
US4325794A (en) 1980-06-02 1982-04-20 Calgon Corporation Combined visible light and thermally activated continuous polymerization process
US4529782A (en) 1981-09-14 1985-07-16 Union Carbide Corporation High molecular weight water soluble polymers
EP0080539B1 (en) 1981-11-27 1986-05-07 Tsuetaki, George F. Polymers primarily for contact lenses, and contact lenses made from them
US4440918A (en) 1982-01-18 1984-04-03 Minnesota Mining And Manufacturing Company Contact lens containing a fluorinated telechelic polyether
US4544572A (en) 1982-09-07 1985-10-01 Minnesota Mining And Manufacturing Company Coated ophthalmic lenses and method for coating the same
US4569962A (en) 1983-09-19 1986-02-11 Minnesota Mining And Manufacturing Company Perfluoropolyether compositions which are soluble in non-fluorinated solvents
US4581430A (en) 1984-02-01 1986-04-08 Armstrong World Industries, Inc. Acrylate and methacrylate polymers and processes for preparing them
US4863647A (en) 1984-06-28 1989-09-05 Baylor Jr Charles Process for preparation of electrophoresis gel material
CA1268732A (en) 1984-12-27 1990-05-08 Akira Yada Radiation-polymerizing water-soluble cast vinyl monomer layer and forming particles
DE3518673C2 (en) 1985-05-24 1994-08-11 Henkel Kgaa Easily dissolvable preparation of cationic polymers
US4640805A (en) 1985-10-07 1987-02-03 Neefe Charles W Method of selectively tinting cast lenses
US5529728A (en) 1986-01-28 1996-06-25 Q2100, Inc. Process for lens curing and coating
US4740533A (en) 1987-07-28 1988-04-26 Ciba-Geigy Corporation Wettable, flexible, oxygen permeable, substantially non-swellable contact lens containing block copolymer polysiloxane-polyoxyalkylene backbone units, and use thereof
US5185385A (en) 1987-01-13 1993-02-09 Texaco Chemical Company Polymerization process
US4800123A (en) 1987-09-03 1989-01-24 Freeman Chemical Corporation In-mold scratch resistant coating for peroxide curable urethane elastomers
US4895102A (en) * 1987-10-29 1990-01-23 Techna Vision Incorporated Spin coater
US4963159A (en) * 1987-11-24 1990-10-16 Schering Corporation Hydrophilic colored contact lens
US4874827A (en) 1988-03-09 1989-10-17 Hart Chemical Limited Production of highly-dispersible water-soluble polymers
US5010155A (en) 1988-09-28 1991-04-23 Ciba-Geigy Corporation Vinyl-urethane substituted hydroxyethyl cellulose
EP0362137A3 (en) 1988-09-28 1991-09-04 Ciba-Geigy Ag Molded polymers with hydrophilic surfaces, and process for making them
US5055602A (en) 1989-05-02 1991-10-08 Bausch & Lomb Incorporated Polymerizable dye
US5070215A (en) 1989-05-02 1991-12-03 Bausch & Lomb Incorporated Novel vinyl carbonate and vinyl carbamate contact lens material monomers
US5034461A (en) 1989-06-07 1991-07-23 Bausch & Lomb Incorporated Novel prepolymers useful in biomedical devices
US5397848A (en) * 1991-04-25 1995-03-14 Allergan, Inc. Enhancing the hydrophilicity of silicone polymers
ES2090710T3 (en) 1991-11-05 1996-10-16 Bausch & Lomb HUMECTABLE SILICONE HYDROGEL COMPOSITIONS AND METHODS FOR ITS MANUFACTURE.
NZ248969A (en) 1992-10-26 1995-08-28 Johnson & Johnson Vision Prod Tinted contact lens; method of preparation using reactive monomer-halotriazine dye adjunct
US5316700A (en) * 1992-11-02 1994-05-31 Wesley-Jessen Corporation Method and apparatus for removing excess lens forming material
DE4310643A1 (en) 1993-04-01 1994-10-06 Merck Patent Gmbh Cyclic adhesion inhibitors
US5667735A (en) 1994-05-23 1997-09-16 2C Optics, Inc. Opthalmic mold coatings
US5804107A (en) * 1994-06-10 1998-09-08 Johnson & Johnson Vision Products, Inc. Consolidated contact lens molding
US5760100B1 (en) * 1994-09-06 2000-11-14 Ciba Vision Corp Extended wear ophthalmic lens
US5779943A (en) * 1996-03-19 1998-07-14 Johnson & Johnson Vision Products, Inc. Molded polymeric object with wettable surface made from latent-hydrophilic monomers
AR008108A1 (en) 1996-08-01 1999-12-09 Novartis Ag A METHOD FOR FORMING A RADIATION ABSORBENT POLYMERIC ARTICLE, A POLYMERIC ARTICLE SO FORMED, AND A METHOD FOR FORMING A POLYMERIC DYE
DE19636266A1 (en) * 1996-09-06 1998-03-12 Kaltenbach & Voigt Method and device for curing photosensitive polymeric compositions
US6169127B1 (en) * 1996-08-30 2001-01-02 Novartis Ag Plasma-induced polymer coatings
US6486262B1 (en) * 1997-06-06 2002-11-26 Nippon Zeon Co., Ltd. Molding material for plastic lens
US5945465A (en) * 1998-05-15 1999-08-31 Bausch & Lomb Incorporated Method for polymerizing contact lenses having UV absorbing properties
US6217171B1 (en) 1998-05-26 2001-04-17 Novartis Ag Composite ophthamic lens
US6087415A (en) * 1998-06-11 2000-07-11 Johnson & Johnson Vision Care, Inc. Biomedical devices with hydrophilic coatings
AU750236B2 (en) * 1998-07-17 2002-07-11 Biocompatibles Uk Limited Method for providing coated moulded polymeric articles
US6818018B1 (en) * 1998-08-14 2004-11-16 Incept Llc In situ polymerizable hydrogels
US6099852A (en) * 1998-09-23 2000-08-08 Johnson & Johnson Vision Products, Inc. Wettable silicone-based lenses
US20010036556A1 (en) 1998-10-20 2001-11-01 James S. Jen Coatings for biomedical devices
DE60001457T2 (en) * 1999-06-11 2003-09-11 Bausch & Lomb LENS MOLDING TOOLS WITH PROTECTIVE LAYER FOR THE PRODUCTION OF CONTACT LENSES AND INTRAOCULAR LENSES
AUPQ326399A0 (en) 1999-09-21 1999-10-28 Sola International Holdings Ltd Method of coating an optical element
CN1313842C (en) * 1999-10-12 2007-05-02 庄臣及庄臣视力保护公司 Contact lens coating selection and manufacturing process thereof
US6478423B1 (en) * 1999-10-12 2002-11-12 Johnson & Johnson Vison Care, Inc. Contact lens coating selection and manufacturing process
US6406739B1 (en) * 2000-01-12 2002-06-18 Alcon Universal Ltd. Coating compositions and methods for reducing edge glare in implantable ophthalmic lenses
US6719929B2 (en) * 2000-02-04 2004-04-13 Novartis Ag Method for modifying a surface
US6551531B1 (en) * 2000-03-22 2003-04-22 Johnson & Johnson Vision Care, Inc. Molds for making ophthalmic devices
AR029901A1 (en) * 2000-03-24 2003-07-23 Novartis Ag RETICULABLE OR POLYMERIZABLE PREPOLIMEROS, AND A PROCESS FOR THE MANUFACTURE OF '' BIOMEDICAL '' '' MOLDED ITEMS
US6706836B1 (en) * 2000-03-31 2004-03-16 Avery Dennison Corporation Hydrophilic polymers, pressure sensitive adhesives and coatings
US6248266B1 (en) * 2000-08-11 2001-06-19 Bausch & Lomb Incorporated Method of making lens with colored portion
US6832887B2 (en) 2002-04-09 2004-12-21 K-Tron Technologies, Inc. Bulk material pump feeder

Also Published As

Publication number Publication date
DE60219318T2 (en) 2008-01-03
DE60219318D1 (en) 2007-05-16
JP4387189B2 (en) 2009-12-16
AR035263A1 (en) 2004-05-05
CA2456036C (en) 2010-09-21
CN1564732A (en) 2005-01-12
WO2003011551A1 (en) 2003-02-13
AU2002322750B2 (en) 2007-09-20
US20030052424A1 (en) 2003-03-20
KR100886580B1 (en) 2009-03-05
CN1289277C (en) 2006-12-13
TW590868B (en) 2004-06-11
EP1412154A1 (en) 2004-04-28
EP1412154B1 (en) 2007-04-04
KR20040029392A (en) 2004-04-06
JP2005520703A (en) 2005-07-14
BR0211644B1 (en) 2011-09-06
HK1063611A1 (en) 2005-01-07
BR0211644A (en) 2004-07-13
US7879267B2 (en) 2011-02-01

Similar Documents

Publication Publication Date Title
CA2456036A1 (en) Method for coating articles by mold transfer
EP1194273B1 (en) Lens molds with protective coatings for production of contact lenses and intraocular lenses
TWI509312B (en) Silicone hydrogel contact lenses and methods of making silicone hydrogel contact lenses
CA2248467C (en) Molded polymer article having a hydrophilic surface and process for producing the same
EP1585630B1 (en) Methods for the extraction of contact lenses
US7833443B2 (en) Molds for producing contact lenses
KR101696014B1 (en) Ophthalmic lens molds with low levels of uv light transmittance, ophthalmic lenses molded therein, and related methods
MX2008015849A (en) Wettable silicone hydrogel contact lenses and related compositions and methods.
AU2002322750A1 (en) Method for in mold coating hydrogel articles
SG173578A1 (en) Wettable hydrogel materials for use in ophthalmic applications and methods
JP5631655B2 (en) Contact lens and manufacturing method thereof
CA2635612A1 (en) Silicone containing polymers formed from non-reactive silicone containing prepolymers
JPH02140718A (en) Contact lens material and making thereof
JP2002047365A (en) Method of preparing surface-treated plastic molding
CA2646659C (en) Demolding aids for silicone hydrogels and related methods
CA2371965A1 (en) Colorants for use in tinted contact lenses and methods for their production
WO2018229475A1 (en) Method of manufacturing coated silicone hydrogel contact lenses
US20100331443A1 (en) Silicone hydrogels formed from symmetric hydroxyl functionalized siloxanes

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20200831