WO2001002881A1 - Procede d'elimination d'extractibles a partir de lentilles de contact polymeres - Google Patents
Procede d'elimination d'extractibles a partir de lentilles de contact polymeres Download PDFInfo
- Publication number
- WO2001002881A1 WO2001002881A1 PCT/US2000/016172 US0016172W WO0102881A1 WO 2001002881 A1 WO2001002881 A1 WO 2001002881A1 US 0016172 W US0016172 W US 0016172W WO 0102881 A1 WO0102881 A1 WO 0102881A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- solvent
- vapor
- extractables
- lenses
- contact lens
- Prior art date
Links
Classifications
-
- 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
-
- 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
- B29C71/00—After-treatment of articles without altering their shape; Apparatus therefor
- B29C71/009—After-treatment of articles without altering their shape; Apparatus therefor using gases without chemical reaction
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/02—Chemical treatment or coating of shaped articles made of macromolecular substances with solvents, e.g. swelling agents
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
-
- 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
- B29C71/00—After-treatment of articles without altering their shape; Apparatus therefor
- B29C71/0009—After-treatment of articles without altering their shape; Apparatus therefor using liquids, e.g. solvents, swelling agents
- B29C2071/0036—Extracting, degassing, removing gases from moulded articles
-
- 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
Definitions
- the present invention relates to contact lens manufacture and, more particularly, to an improved process for removing extractables from polymeric contact lenses.
- Hydrogels represent a desirable class of materials for the manufacture of contact lenses.
- a hydrogel is a hydrated cross-linked polymeric system that contains water in an equilibrium state.
- Hydrogel lenses offer relatively high oxygen permeability as well as desirable biocompatibility and comfort.
- a composition containing a diluent and suitable monomers is charged to a mold and cured.
- the molded lens can be subjected to machining operations such as lathe cutting, buffing, and polishing and further subjected to extraction, hydration, and sterilization procedures.
- Residual material which may be either hydrophilic or hydrophobic, include solvents, unreacted monomers, or low molecular weight oligomers. Residual materials are referred to herein as "extractables". Hydrophilic residual materials can be extracted by water whereas hydrophobic residual components are typically removed by extraction with water- miscible organic solvents, in particular, alcohols such as isopropyl alcohol. Following the alcohol extraction process, the lens needs to be hydrated by treatment with water before being sterilized by, for example, autoclaving in buffered saline.
- Removal of extractable hydrophobic components from contact lenses is typically carried out by immersing the lenses in the extraction solvent for a period of time to ensure removal of the components.
- Manufacturing contact lenses on a commercial scale requires the replacement and disposal of large volumes of spent solvent, which is undesirable both economically and environmentally. Finding a way of reducing the amount of spent extraction solvent needing to be replaced and disposed of would be desirable.
- the present invention provides such a way.
- the present invention is directed to an improved process for treating contact lenses.
- the improvement comprises contacting a polymeric contact lens containing extractables with substantially pure vapor or substantially pure condensate of the vapor of a volatile solvent that is effective for dissolving and thereby removing the extractables from the contact lens.
- FIG. 1 schematically depicts a lens extraction process of the prior art.
- FIG. 2 schematically depicts the improved process of the present invention.
- Hydrogel lenses are generally formed of a copolymer of at least one hydrophilic monomer and a cross linking monomer.
- the hydrophilicity is due to the presence of hydrophilic groups such as, for example, hydroxy, carboxylic acid, amide and sulfonic acid.
- the swollen equilibrated state results from a balance between the osmotic driving forces that cause the water to enter the hydrophilic polymer and the forces exerted by the polymer chains in resisting expansion.
- the copolymeric material further includes a silicone-containing monomer.
- Lenses in this class are generally formed of a copolymer of at least one hydrophilic monomer and a cross-linking monomer.
- Hydrophilic monomers include those known in the art such as: unsaturated carboxylic acids such as methacrylic acid and acrylic acid; (meth)acrylic substituted alcohols or glycols such as 2-hydroxyethyl mefhacrylate, 2-hydroxyethyl acrylate, and glyceryl mefhacrylate; vinyl lactams such as N-vinyl-2-pyrrolidone; and acrylamides such as methacrylamide and N,N-dimethylacrylamide. Further examples of such hydrophilic monomers can be found in U.S. Patent Nos. 4,153,641; 4,740,533; 5,034,461 ; and 5,070,215, the disclosures of which are incorporated herein by reference.
- the cross-linking monomer may be material having multiple polymerizable functionalities, preferably vinyl functionalities.
- Representative cross-linking monomers include: divinylbenzene, allyl methacrylate, ethylene glycol dimethacrylate, tetraethyleneglycol dimethacrylate, polyethyleneglycol dimethacrylate, and vinylcarbonate derivatives of the glycol dimethacrylates.
- the copolymeric material further includes at least one silicone-containing monomer.
- organic diluent is included in the initial monomeric mixture.
- organic diluent encompasses organic compounds that minimize incompatibility of the components in the initial monomeric mixture and are substantially nonreactive with the components in the initial mixture. Additionally, the organic diluent serves to minimize phase separation of polymerized products produced by polymerization of the monomeric mixture. Also, the organic diluent will generally lower the glass transition temperature of the reacting polymeric mixture, which allows for a more efficient curing process and ultimately results in a more uniformly polymerized product. Uniformity of the initial monomeric mixture and the polymerized product are of particular concern for silicone hydrogels primarily due to the inclusion of silicone- containing monomers.
- Contemplated organic diluents include: monohydric alcohols, with C 6 -C 10 straight-chained aliphatic monohydric alcohols being especially preferred; diols such as ethylene glycol; polyols such as glycerin; ethers such as diethylene glycol monoethyl ether; ketones such as methyl ethyl ketone; esters such as methyl heptanoate; and hydrocarbons such as toluene.
- a preferred diluent is nonanol, a C 9 alcohol.
- the organic diluent is sufficiently volatile to facilitate its removal from a cured article by evaporation at or near ambient pressure.
- a casting process may yield a shaped article having the desired posterior and anterior lens surfaces.
- a monomeric mixture can be charged to a mold comprising a first mold section including a surface for forming a desired anterior lens surface and a second mold section including a surface for forming a desired posterior lens surface.
- the monomeric mixture can be charged to an open mold having a surface for forming a desired anterior lens surface, and a desired posterior lens surface is formed from rotation of the mold.
- machining operations subsequent to the curing of the article, may still be necessary to provide a contact lens more suitable for placement on the eye. Such machining operations include lathe cutting the lens to obtain a desired lens edge, buffing the lens edge, or polishing the lens edge or surface.
- the casting process may yield a shaped article which does not have the desired anterior and/or posterior lens surfaces. Accordingly, the casting process is followed by a machining operation to form a desired lens surface.
- a machining operation to form a desired lens surface.
- U.S. Patent No. 4,555,732 the disclosure of which is incorporated herein by reference, describes a process where an excess of a monomeric mixture is cured by spincasting in a mold to form a shaped article having an anterior lens surface and a relatively large thickness, and the posterior surface of the cured spincast article is subsequently lathe cut to provide a contact lens having the desired thickness and posterior surface. Further machining operations such as the previously described edge finishing operations may follow the lathe cutting of the lens surface.
- Removal of extractable components from contact lenses is typically carried out by contacting the lenses with an extraction solvent for a period of time sufficient to ensure substantially complete removal of the components.
- a batch of contact lenses is immersed in a bath of isopropyl alcohol and held for several hours to effect removal of extractables such as monomers and oligomers from the lenses.
- the lenses are removed, and a new batch is immersed in the bath. After several hours holding, this batch is removed, and the process is repeated.
- the isopropyl alcohol bath is reused, several thousand contact lenses being extracted with a given quantity of isopropyl alcohol before it is replaced with fresh solvent.
- FIG. 1 is schematically depicted a lens extraction process of the prior art.
- One or more contact lenses 10 in a holder 11 is immersed in a solvent 12 in a vessel 13.
- Solvent 12 acts to dissolve extractable components (not shown) and thereby remove them from lenses 10.
- the contact lens is contacted with the vapor or vapor condensate of substantially pure solvent for a period of time effective to remove substantially all extractables such as, for example, monomers or oligomers, from the lens.
- the contact lens preferably is formed from a hydrogel, more preferably, a silicone hydrogel.
- the extraction solvent preferably has a boiling point of up to about 200°C at atmospheric pressure. More preferably, the boiling point of the solvent is 100°C or less (at atmospheric pressure) to ensure that substantially all the extractables removed from the lenses remain condensed in the bulk solvent and are not included in the vapor generated therefrom.
- the extraction solvent is an organic solvent, which can be selected from the group consisting of alcohols, glycols, ketones, ethers, alkanes, and aromatic hydrocarbons, is preferably an alcohol containing up to about 8 carbon atoms.
- a particularly preferred extraction solvent is isopropyl alcohol.
- FIG. 2 schematically represents the improved process of the present invention.
- Contact lenses 10 in holder 11 are suspended above solvent 12 contained in a closed vessel 23.
- Solvent 12 is heated above its boiling point by a source of heat 24.
- vessel 23 is a condenser 25.
- the resulting solvent vapor 26 and its condensate droplets 27 contact lenses 10 and dissolve extractables (not shown) contained in lenses 10 and transport the extractable components to the bulk solvent 12. Because the extractables are much less volatile than solvent 12, vapor 26 and condensate droplets 27 are composed of substantially pure solvent 12.
- the extractables removed from lenses 10 are thereby concentrated in bulk solvent 12.
- the process can be run substantially continuously; upon completion of the treatment of a batch of lenses 10, they can be removed and replaced by a new batch.
- the improved process of the present invention provides for the extraction of the lenses with substantially pure solvent vapor or condensate, there is no loss in extraction efficiency.
- the solvent can be replaced after extraction of a specified number of lenses, but this number can be substantially increased over that of current practice, resulting in large savings in the cost of spent solvent disposal and replacement.
- a further advantage of the improved process of the present invention lies in the fact that the solvent-extracted lenses contain less residual solvent to be removed in a subsequent hydration step.
- the lenses may be obtained dry and unwa ⁇ ed, enabling them to be surface treated immediately following the extraction step.
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- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Optics & Photonics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Plasma & Fusion (AREA)
- Manufacturing & Machinery (AREA)
- Ophthalmology & Optometry (AREA)
- Mechanical Engineering (AREA)
- Eyeglasses (AREA)
Abstract
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU56090/00A AU5609000A (en) | 1999-07-01 | 2000-06-13 | Process for removing extractables from polymeric contact lenses |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US14215999P | 1999-07-01 | 1999-07-01 | |
US60/142,159 | 1999-07-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001002881A1 true WO2001002881A1 (fr) | 2001-01-11 |
Family
ID=22498771
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2000/016172 WO2001002881A1 (fr) | 1999-07-01 | 2000-06-13 | Procede d'elimination d'extractibles a partir de lentilles de contact polymeres |
Country Status (2)
Country | Link |
---|---|
AU (1) | AU5609000A (fr) |
WO (1) | WO2001002881A1 (fr) |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002036669A2 (fr) * | 2000-11-03 | 2002-05-10 | Johnson & Johnson Vision Care, Inc. | Solvants utiles dans la preparation de polymeres contenant des monomeres hydrophiles et hydrophobes |
WO2003068846A1 (fr) * | 2002-02-18 | 2003-08-21 | Nkt Research & Innovation A/S | Procedes pour traiter des substrats polymeres |
WO2003082367A2 (fr) * | 2002-03-28 | 2003-10-09 | Bausch & Lomb Incorporated | Procede d'elimination de matieres extractibles se trouvant dans des dispositifs biomedicaux |
WO2005113028A1 (fr) * | 2004-05-21 | 2005-12-01 | Bausch & Lomb Incorporated | Procédé pour extraire des dispositifs biomédicaux |
WO2007075604A1 (fr) * | 2005-12-21 | 2007-07-05 | Bausch & Lomb Incorporated | Procede de moulage et d’extraction de dispositifs biomedicaux |
WO2009025845A1 (fr) * | 2007-08-21 | 2009-02-26 | Johnson & Johnson Vision Care, Inc. | Procédés de formation d'un précurseur de lentille ophtalmique, et lentille |
US7905594B2 (en) | 2007-08-21 | 2011-03-15 | Johnson & Johnson Vision Care, Inc. | Free form ophthalmic lens |
US8240849B2 (en) | 2009-03-31 | 2012-08-14 | Johnson & Johnson Vision Care, Inc. | Free form lens with refractive index variations |
US9266294B2 (en) | 2007-08-21 | 2016-02-23 | Johnson & Johnson Vision Care, Inc. | Apparatus for formation of an ophthalmic lens precursor and lens |
US9346226B2 (en) | 2010-03-12 | 2016-05-24 | Johnson & Johnson Vision Care, Inc. | Apparatus for vapor phase processing ophthalmic devices |
US9417464B2 (en) | 2008-08-20 | 2016-08-16 | Johnson & Johnson Vision Care, Inc. | Method and apparatus of forming a translating multifocal contact lens having a lower-lid contact surface |
US9610742B2 (en) | 2007-08-21 | 2017-04-04 | Johnson & Johnson Vision Care, Inc. | Apparatus for formation of an ophthalmic lens precursor and lens |
US9645412B2 (en) | 2014-11-05 | 2017-05-09 | Johnson & Johnson Vision Care Inc. | Customized lens device and method |
US10359643B2 (en) | 2015-12-18 | 2019-07-23 | Johnson & Johnson Vision Care, Inc. | Methods for incorporating lens features and lenses having such features |
CN110382211A (zh) * | 2017-01-09 | 2019-10-25 | 增材制造技术有限公司 | 增材制造的改进 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1991004288A1 (fr) * | 1989-09-14 | 1991-04-04 | Chang Sing Hsiung | Lentille de contact souple, non irritante et permeable au gaz et methode de fabrication |
WO1996026059A1 (fr) * | 1995-02-22 | 1996-08-29 | Novartis Ag | Procede de degagement, d'extraction et de nettoyage d'articles polymeres a l'aide d'un fluide supercritique |
JPH1075971A (ja) * | 1996-09-02 | 1998-03-24 | Menicon Co Ltd | 眼用レンズの製造方法 |
-
2000
- 2000-06-13 AU AU56090/00A patent/AU5609000A/en not_active Abandoned
- 2000-06-13 WO PCT/US2000/016172 patent/WO2001002881A1/fr active Application Filing
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1991004288A1 (fr) * | 1989-09-14 | 1991-04-04 | Chang Sing Hsiung | Lentille de contact souple, non irritante et permeable au gaz et methode de fabrication |
WO1996026059A1 (fr) * | 1995-02-22 | 1996-08-29 | Novartis Ag | Procede de degagement, d'extraction et de nettoyage d'articles polymeres a l'aide d'un fluide supercritique |
JPH1075971A (ja) * | 1996-09-02 | 1998-03-24 | Menicon Co Ltd | 眼用レンズの製造方法 |
Non-Patent Citations (1)
Title |
---|
PATENT ABSTRACTS OF JAPAN vol. 1998, no. 08 30 June 1998 (1998-06-30) * |
Cited By (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002036669A2 (fr) * | 2000-11-03 | 2002-05-10 | Johnson & Johnson Vision Care, Inc. | Solvants utiles dans la preparation de polymeres contenant des monomeres hydrophiles et hydrophobes |
WO2002036669A3 (fr) * | 2000-11-03 | 2003-03-06 | Johnson & Johnson Vision Care | Solvants utiles dans la preparation de polymeres contenant des monomeres hydrophiles et hydrophobes |
US6765083B2 (en) | 2000-11-03 | 2004-07-20 | Johnson & Johnson Vision Care, Inc. | Solvents useful in the preparation of polymers containing hydrophilic and hydrophobic monomers |
US7112652B2 (en) | 2000-11-03 | 2006-09-26 | Johnson & Johnson Vision Care, Inc. | Solvents useful in the preparation of polymers containing hydrophilic and hydrophobic monomers |
WO2003068846A1 (fr) * | 2002-02-18 | 2003-08-21 | Nkt Research & Innovation A/S | Procedes pour traiter des substrats polymeres |
WO2003082367A2 (fr) * | 2002-03-28 | 2003-10-09 | Bausch & Lomb Incorporated | Procede d'elimination de matieres extractibles se trouvant dans des dispositifs biomedicaux |
WO2003082367A3 (fr) * | 2002-03-28 | 2003-12-04 | Bausch & Lomb | Procede d'elimination de matieres extractibles se trouvant dans des dispositifs biomedicaux |
WO2005113028A1 (fr) * | 2004-05-21 | 2005-12-01 | Bausch & Lomb Incorporated | Procédé pour extraire des dispositifs biomédicaux |
WO2007075604A1 (fr) * | 2005-12-21 | 2007-07-05 | Bausch & Lomb Incorporated | Procede de moulage et d’extraction de dispositifs biomedicaux |
US7905594B2 (en) | 2007-08-21 | 2011-03-15 | Johnson & Johnson Vision Care, Inc. | Free form ophthalmic lens |
US9857607B2 (en) | 2007-08-21 | 2018-01-02 | Johnson & Johnson Vision Care, Inc. | Apparatus for formation of an ophthalmic lens precursor and lens |
US10901319B2 (en) | 2007-08-21 | 2021-01-26 | Johnson & Johnson Vision Care, Inc. | Apparatus for forming an ophthalmic lens |
JP2015084100A (ja) * | 2007-08-21 | 2015-04-30 | ジョンソン・アンド・ジョンソン・ビジョン・ケア・イン | 眼科レンズを形成する方法 |
WO2009025845A1 (fr) * | 2007-08-21 | 2009-02-26 | Johnson & Johnson Vision Care, Inc. | Procédés de formation d'un précurseur de lentille ophtalmique, et lentille |
US9180634B2 (en) | 2007-08-21 | 2015-11-10 | Johnson & Johnson Vision Care, Inc. | Methods for formation of an ophthalmic lens precursor and lens |
US9180633B2 (en) | 2007-08-21 | 2015-11-10 | Johnson & Johnson Vision Care, Inc. | Methods for formation of an ophthalmic lens precursor and lens |
US9266294B2 (en) | 2007-08-21 | 2016-02-23 | Johnson & Johnson Vision Care, Inc. | Apparatus for formation of an ophthalmic lens precursor and lens |
US10571718B2 (en) | 2007-08-21 | 2020-02-25 | Johnson & Johnson Vision Care, Inc | Apparatus for formation of an ophthalmic lens precursor and lens |
US9610742B2 (en) | 2007-08-21 | 2017-04-04 | Johnson & Johnson Vision Care, Inc. | Apparatus for formation of an ophthalmic lens precursor and lens |
US10126567B2 (en) | 2007-08-21 | 2018-11-13 | Johnson & Johnson Vision Care, Inc. | Apparatus for formation of an ophthalmic lens precursor and lens |
US9417464B2 (en) | 2008-08-20 | 2016-08-16 | Johnson & Johnson Vision Care, Inc. | Method and apparatus of forming a translating multifocal contact lens having a lower-lid contact surface |
US8157373B2 (en) | 2009-03-02 | 2012-04-17 | Johnson & Johnson Vision Care, Inc. | Free form ophthalmic lens |
US9075186B2 (en) | 2009-03-31 | 2015-07-07 | Johnson & Johnson Vision Care, Inc. | Free form lens with refractive index variations |
US8240849B2 (en) | 2009-03-31 | 2012-08-14 | Johnson & Johnson Vision Care, Inc. | Free form lens with refractive index variations |
US9346226B2 (en) | 2010-03-12 | 2016-05-24 | Johnson & Johnson Vision Care, Inc. | Apparatus for vapor phase processing ophthalmic devices |
US9645412B2 (en) | 2014-11-05 | 2017-05-09 | Johnson & Johnson Vision Care Inc. | Customized lens device and method |
US10359643B2 (en) | 2015-12-18 | 2019-07-23 | Johnson & Johnson Vision Care, Inc. | Methods for incorporating lens features and lenses having such features |
CN110382211A (zh) * | 2017-01-09 | 2019-10-25 | 增材制造技术有限公司 | 增材制造的改进 |
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