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WO1994013717A1 - Procede de production d'une lentille de contact douce - Google Patents

Procede de production d'une lentille de contact douce Download PDF

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Publication number
WO1994013717A1
WO1994013717A1 PCT/CA1992/000529 CA9200529W WO9413717A1 WO 1994013717 A1 WO1994013717 A1 WO 1994013717A1 CA 9200529 W CA9200529 W CA 9200529W WO 9413717 A1 WO9413717 A1 WO 9413717A1
Authority
WO
WIPO (PCT)
Prior art keywords
acrylamide
bis
soft contact
contact lens
methylene
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.)
Ceased
Application number
PCT/CA1992/000529
Other languages
English (en)
Inventor
Anatoliy Mihailovich Sokolyuk
Natalia Vladimirovna Kokosha
Zoya Rudolfovna Ulberg
Fyodor Danilovich Ovcharenko
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.)
958075 Ontario Inc
Original Assignee
958075 Ontario Inc
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 958075 Ontario Inc filed Critical 958075 Ontario Inc
Priority to AU30789/92A priority Critical patent/AU3078992A/en
Priority to PCT/CA1992/000529 priority patent/WO1994013717A1/fr
Publication of WO1994013717A1 publication Critical patent/WO1994013717A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F220/56—Acrylamide; Methacrylamide
    • 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

Definitions

  • the present invention relates to the sphere of obtaining medical materials from cross-linked polymeric hydrogele; specifically, to a method of obtaining a soft contact lens , which can be used in medical practice.
  • U.S. Patent 4,430,458 describes a cross-linked hydrogel polymeric material intended for contact lenses.
  • the process of obtaining contact lenses from the hydrogel material containing at least 65% by weight of water includes polymerization in the form of mixed monomers:
  • a poly- merizable hydrophobic vinyl monomer which is at least one monomer selected from the group consisting of vinyl aromatic hydrocarbons of the styrene type and hydrophobic es ⁇ er of acrylic or methacrylic acid.
  • the initiator is, for example, methyl ethyl ke ⁇ one peroxide
  • the cross-linking agent for example, ethylene glycol dimethacrylate
  • the process of polymerization in the form continues for 48 hours at 60°-100°; the linking of the polymer is initiated by exposure to light. As a result a hard contact lense is received. It is then cut and immersed in an aqueous medium for 4 days. After saturation it contains 65-70% by weight of water.
  • the hydrogel is harder to use for soft contact lenses and other medical products.
  • the GB 21,145,786 method is designed to produce poly- acrylamide gel for medical and biological purposes and boils down to this:
  • A,B and C initial solutions are prepared for polymerization.
  • the A solution is prepared by dissolving 5 ml of H,N,N',N'-tetramethylethylenediamine in 995 ml of distilled water.
  • the B solution is obtained by dissolving 7.35 g M,N'-methylene-bis-acrylamide in 350 ml distilled water heated to 60°C, filtering the solution, adding 280 g acrylamide and then up to 1,000 ml distilled water.
  • the C solution is prepared by dissolving 1.4 g ammonium persulphate in 1,000 ml distilled water.
  • the solutions thus prepared are mixed: 2 parts of B solution, 4 parts of C solution, and 1 part of A solution, so as to receive a reaction mix.
  • This reaction mix is then placed in the form for polymerization. It can consist of two parallel plates, or a reac tor whose inner surface repeats the form of the contact less. After the polymerization of the reaction mix, which lasts for 3 - 15 min, a cross-linked polyacrylamide gel is received, which can be used as an artificial medium for microorganisms, also as soft contact lenses and artificial lenses of the eye.
  • the cross-linked polyacrylamide gel thus obtained contains (in percent by weight of mass):
  • polyacrylamide gel proves moat effective when used as an artificial medium-for growing-microorganisms. Its use as soft-durable contact lenses is less-preferable, in that it shows-low physical-mechanical characteristics.
  • the first step is to prepare initial solutions for polymerization with the following con- o ⁇ ntration (g/l):
  • the contact lense thus obtained is retrieved from the form and rinsed in 10-15 ml distilled water or sterile 0.85ft sodium chloride solution for 20-30 min, with solution 1 being changed three times.
  • Soft contact lenses produced according to the above method possess sufficiently high physical-mechanical characteristics only when sufficiently thick, which hinders their adjustment to the eye apple. Besides, the thicker the lens, the lower its diffusive performance.
  • the material of the soft contact lens to excercise free transportation of K + , Na + , Ca ++ ions and oxygen which ensure the normal funotion- ing of the cornea when wearing durable oontact lenaes.
  • the present invention is aimed at increasing the physical-chemical and diffusive qualities of a soft contact lens with a high water content (up to 97%) and lower thickness.
  • She method of obtaining polyacrylamide gel is implemented as follows.
  • N,N'-methylene-bis-acrylamide used C 7 H 10 N 2 O 3 , mol. mass 154,16, white crystalline odorless powder; melting temperature: 185°C; water dissolvability: 20°C (3g per 100 g water). It is possible to use N.N'-methylene-bis-acrylamide made by Reanal (Hungary), Fluca Chemica (Switzerland) - basic agent: 96.8ft; acrylic acid: 0.02%; that produced by
  • the aforementioned monomers are cleansed of the traces of acrylic acid, for example, by recrystalization.
  • Acrylamide recrystalization' is performed as follows: 70 g acrylamide is dissolved in 1 liter of chloroform at 50-60°C, then the mix is filtered while etill hot. The filtrate is cooled in a refrigerator to -15-20°C. The falling out crystals are tnen filtered off and rinsed on the filter with cold chloroform. After drying out the crystals their melting tem- perature is determined.
  • the content of the basic agent increases to 99.9% when using acrylamide made by Reanal (Hungary) or Aldrich (U.S.). Ko traces of acrylic acid are detected. If acrylamide of
  • N,N'-metnylene-bis-acrylamide is recrystalized in acetone. To do so, 36 g N,N'-methylene-bis-acrylamide is dissolved in one liter of acetone, boiled with reverse refrigeration, let through a filter, then cooled till a temperature below zero, whereupon the fallen out- crystals are filtered off and the melting temperature determined.
  • the content of the basic substance is higher wnen using N.N'-methylene-bis-acrylamide made by Reanal (Hungary), Fluca Chemica (Switzerland), and registers up to 98%. No traces of acrylic acid are detected.
  • N,N'-methylene-bis-acry- lamide of Electran (U.K.) manufature the content of the basic agent reaches 99.94%.
  • the monomers of acrylamide and N,N'-methy- lene-bis-acrylamide can be stored for a month and used to prepare solutions.
  • the monomers of acrylamide and N,N'-methylene-bis-acrylamide are used for the preparation of solutions, the solvent being a sodium chloride solution or any other acceptable solvent - for example, distilled water.
  • An acrylamide solution has a concentration of 310-750 g/l, and that of N.N'-methylene-bis-acrylamide 0.5-9.0 g/l.
  • N,N,N',N'-tetramethylethylenediamine and ammonium persulphate are pre- pared.
  • Ammonium persulphate /NH 4 / 2 S 2 O 8 - molecular mass 228.19; colorless plate-like crystals; density 1.982 g/cm 3 ; decomposition temperature: 120°C; dissolvability: 15.5°C (74.8 g per 100 g water).
  • a solution of N,N,N' ,N'-tetramethylethylenediamine has a concentration of 0.1 - 3.0 g/l, and that of ammonium persul- phate 0.1 -4.0g/l .
  • the ratio of N,N,N',N'-tetramethylethylenediamine and the mix of acrylamide and N,N'-methylene-bis-acrylamide in the polymerizing mix is used in such a way as to ensure that the ratio between N,N,H',N'-tetramethylethylenediamine and the mix of acrylamide -and N,N'-methylene-bis-acrylamide range from 1:6 to 1:25.
  • Ammonium persulphate is added to the polymerizing mix as an initiator.
  • the cross-linked polyacrylamide gel in the form of a soft contact lens is rinsed in 10-15 ml distilled water or sterile sodium chloride solution for 20-30 min (changing solution three times). Then the lens is immersed for 24 till saturated. It can contain 87-98ft by weight of water.
  • Soft contact lenses thus obtained have been used in me- dical practice.
  • Patients treated at AQUALAN, Ltd. (Ukraine) wore continuously soft contact lenses produced following the above procedures for as many as three months and snowed good corrective results.
  • Water content was determined by weighing saturated lenses and those dried to constant weight.
  • Dioptrics of the soft contact lenses were determined using an ordinary dioptometer.
  • the ion diffusion (K + , Na + , Ca ++) and oxygen diffusion coefficients were determined by comparing the concentration of corresponding ions on both sides of the membrane - in this case the soft contact lens, produced following the above procedures.
  • a soft contact lens was obtained using the method and techniques described above herein.
  • a solution of 310 g/l acrylamide, a solution of N,N , -methylene-bis-acrylamide 9,0 g/l , a solution of 0.1 g/l N,N,N',N'-tetramethylethylenedia- mine, and a solution of 4.0 g/l ammonium persulphate were used.
  • the ratio between N.N,N',N'-tetramethylethylenediamine and the mix of acrylamide and N,N'-methylene-bis-acrylamide was 1:6.
  • the time of polymerization 60 min.
  • Temperature +25°C.
  • the soft contact lens thus obtained was -3D.
  • a soft contact lens was obtained using the method and techniques described above herein.
  • Acrylamide and N,N'-methylene-bis-acrylamide were first purified by means of recrystalization.
  • a solution of 750 g/l acrylamide, that of 0.5 g/l N.N'-methylene-bis-acrylamide, 3.0 g/l N,N,N',N'-tetramethylethylenediamine, and 0.1 g/l ammonium persulphate were used.
  • Time of polymerization 45 min; temperature: 25°C.
  • the soft contact lense obtained was -10 D.
  • a ⁇ oft contact lens was produced using the method and techniques described above herein.
  • This soft contact lens was tested for thickness, relative elongation, elasticity, refraction coefficient, water content, and the coefficients of ion (Ha + , K + , Ca ++ ) and oxygen diffusion.
  • a soft contact lens was obtained using the method and techniques described above herein.
  • the soft contact lens thus obtained was +5 D.
  • the soft contact lens was also tested for thickness, relative elongation, elasticity, water content, refraction coefficient and the coefficients of ion (Na + , K + , Ca ++ ) and oxygen diffusion.
  • a soft contact lens was obtained using the method and techniques de ⁇ cribed abover herein.
  • the soft contact lens thus obtained registered -9.5 D.
  • the soft contact lens was also tested for thickness, relative elongation, elasticity, water content and refraction coefficient, as well as for the coefficients of ion (Na + , K + , Ca ++ ) and oxygen diffusion.
  • a soft contact lens was obtained using the method and techniques described above herein.
  • solutions of 500 g/l acrylamide, 0.4 g/l N,N'-bis-acrylamide, 0.05 g/l N,N,N',N'- tetramethylethylenediamine, and 0.06 g/l ammonium persulphate 500 g/l acrylamide, 0.4 g/l N,N'-bis-acrylamide, 0.05 g/l N,N,N',N'- tetramethylethylenediamine, and 0.06 g/l ammonium persulphate.
  • the ratio between the solution N,N,N',N'-tetramethylethylenediamine and the mix of solutions of acrylamide and N,N'-bisacrylamide was 1:7.
  • the soft contact lens was also tested for thickness, relative elongation, elasticity, water content, refraction coefficient, as well as for the coefficients of ion (Na + , K + , Ca ++ ) and oxygen diffusion.
  • a soft contact lens was produced using the method and techniques described above herein(see Example 1).
  • the soft contact lens thus obtained was tested for thickness, relative elongation, elasticity, water content, ion (Na + , K + , Ca ++ ) and oxygen diffusion coefficients.
  • a soft contact lense was received using the method and techniques described in Example 2.
  • the soft contact lens thus obtained was tested for thickness, relative elongation, elasticity, water content, coefficients of ion (Na + , K + , Ca ++ ) and oxygen diffusion.
  • a soft contact lens was produced using the method and techniques described in Example 3.
  • the soft contact lens thus obtained was tested for thickness, relative elongation, elasticity, water content. ion (Ha + , K + , Ca ++ ) and oxygen diffusion coefficients.
  • Table 1 shows that the method and techniques of obtaining soft contact lenses, as laid down in the preaent invention (Example 1 - 3), unlike the conventional method (SU,A, 959,313) produces soft contact lenses of lesser thickness but with higher physical-mechanical and diffusive properties, which makes it possible to use them as soft durable contact lenses worn continuously over considerable periods.
  • comparative analysis (Example 4-9) testifies to the significance of all the parameters contained in the formula of the present invention, in that they distinguish the present method from all the other known methods and techniques.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Eyeglasses (AREA)

Abstract

Selon ce procédé d'obtention d'une lentille de contact solide, une acrylamide et une acrylamide-méthylène-bis-N,N' sont d'abord purifiées et ensuite utilisées pour préparer des solutions de 310 à 750 g/l d'acrylamide, 0,5 à 9,0 g/l d'acrylamide-méthylène-bis-N,N', 0,1 à 3,0 g/l de tétraméthyléthylènediamine N,N,N'N', et 0,1 à 4,0 g/l de persulphate d'ammoniaque. Ces solutions sont mélangées et placées dans le moule de manière à obtenir simultanément une polymérisation et une réticulation, pendant un temps suffisant pour la production d'un matériau hydrogel sous la forme d'une lentille de contact souple. Après avoir été retirée du moule, la lentille est saturée avec de l'eau jusqu'à l'état d'équilibre.
PCT/CA1992/000529 1992-12-04 1992-12-04 Procede de production d'une lentille de contact douce Ceased WO1994013717A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU30789/92A AU3078992A (en) 1992-12-04 1992-12-04 A method for the production of a soft contact lens
PCT/CA1992/000529 WO1994013717A1 (fr) 1992-12-04 1992-12-04 Procede de production d'une lentille de contact douce

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CA1992/000529 WO1994013717A1 (fr) 1992-12-04 1992-12-04 Procede de production d'une lentille de contact douce

Publications (1)

Publication Number Publication Date
WO1994013717A1 true WO1994013717A1 (fr) 1994-06-23

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ID=4172949

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Application Number Title Priority Date Filing Date
PCT/CA1992/000529 Ceased WO1994013717A1 (fr) 1992-12-04 1992-12-04 Procede de production d'une lentille de contact douce

Country Status (2)

Country Link
AU (1) AU3078992A (fr)
WO (1) WO1994013717A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2400106A (en) * 2003-02-19 2004-10-06 Bioartem Ltd Polyacrylamide gel
US7468398B2 (en) 1994-09-06 2008-12-23 Ciba Vision Corporation Extended wear ophthalmic lens
US8568626B2 (en) 1994-09-06 2013-10-29 Ciba Vision Corporation Extended wear ophthalmic lens
EP4241797A2 (fr) * 2014-04-18 2023-09-13 Benz Research And Development Corporation Polymères de (méth)acrylamide pour lentille de contact et lentille intraoculaire

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2114578A (en) * 1979-11-06 1983-08-24 Ki Med I Polyacrylamide gel for medical and biological application and method of its preparation
US4430458A (en) * 1981-10-08 1984-02-07 Kelvin Lenses Limited Hydrogel-forming polymeric materials

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2114578A (en) * 1979-11-06 1983-08-24 Ki Med I Polyacrylamide gel for medical and biological application and method of its preparation
US4430458A (en) * 1981-10-08 1984-02-07 Kelvin Lenses Limited Hydrogel-forming polymeric materials

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 114, no. 26, 1 July 1991, Columbus, Ohio, US; abstract no. 248264a, UL¡BERG ET AL. 'Structure and mechanical and physical properties of gels on polyacrylamide base' page 33 ;column 2 ; *
DATABASE WPIL Section Ch, Week 8533, 9 October 1985 Derwent Publications Ltd., London, GB; Class A, Page 733, AN 85-201701/33 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7468398B2 (en) 1994-09-06 2008-12-23 Ciba Vision Corporation Extended wear ophthalmic lens
US7538146B2 (en) 1994-09-06 2009-05-26 Ciba Vision Corporation Extended wear ophthalmic lens
US7553880B2 (en) 1994-09-06 2009-06-30 Ciba Vision Corporation Extended wear ophthalmic lens
US8415404B2 (en) 1994-09-06 2013-04-09 Ciba Vision Corporation Extended wear ophthalmic lens
US8568626B2 (en) 1994-09-06 2013-10-29 Ciba Vision Corporation Extended wear ophthalmic lens
GB2400106A (en) * 2003-02-19 2004-10-06 Bioartem Ltd Polyacrylamide gel
GB2400106B (en) * 2003-02-19 2006-07-12 Bioartem Ltd Gel
EP4241797A2 (fr) * 2014-04-18 2023-09-13 Benz Research And Development Corporation Polymères de (méth)acrylamide pour lentille de contact et lentille intraoculaire

Also Published As

Publication number Publication date
AU3078992A (en) 1994-07-04

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