EP2170992A1 - Composé d'hydrogel de silicone pour lentilles de contact souples et lentilles de contact souples fabriquées en utilisant le composé - Google Patents

Composé d'hydrogel de silicone pour lentilles de contact souples et lentilles de contact souples fabriquées en utilisant le composé

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Publication number
EP2170992A1
EP2170992A1 EP07833407A EP07833407A EP2170992A1 EP 2170992 A1 EP2170992 A1 EP 2170992A1 EP 07833407 A EP07833407 A EP 07833407A EP 07833407 A EP07833407 A EP 07833407A EP 2170992 A1 EP2170992 A1 EP 2170992A1
Authority
EP
European Patent Office
Prior art keywords
contact lens
bis
trimethylsilyl
acrylamide
vinyl
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.)
Withdrawn
Application number
EP07833407A
Other languages
German (de)
English (en)
Other versions
EP2170992A4 (fr
Inventor
Tack In Nam
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.)
Bescon Co Ltd
Original Assignee
Bescon Co Ltd
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Filing date
Publication date
Application filed by Bescon Co Ltd filed Critical Bescon Co Ltd
Publication of EP2170992A1 publication Critical patent/EP2170992A1/fr
Publication of EP2170992A4 publication Critical patent/EP2170992A4/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2/00—Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
    • A61F2/02—Prostheses implantable into the body
    • A61F2/14—Eye parts, e.g. lenses or corneal implants; Artificial eyes
    • A61F2/16—Intraocular lenses
    • 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
    • C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
    • C08F226/10—N-Vinyl-pyrrolidone
    • 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
    • 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
    • C08F220/10—Esters
    • C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate

Definitions

  • the present invention relate to a silicone -hydrogel soft contact lens, and more particularly, to a silicone-hydrogel composition for a soft contact lens including 2-hydroxyethyl methacrylate and N,O-bis(trimethylsilyl)acrylamide as a silicone monomer, and a soft contact lens using the same.
  • a contact lens is classified into a hard lens having methyl metacrylate
  • MMA as a basic material
  • HEMA 2-hydroxyethyl methacrylate
  • hydrogel refers to a cross-linking high molecule including much moisture in equilibrium and has a lot of physiological applications including medical high molecule for a contact lens (Reference: US. Patent No. 4300820).
  • hydrogel used for lenses includes mostly 2-hydroxyethyl methacrylate as a monomer which is mixed with a small amount of a cross-linking agent and manufactured by a radical thermal polymerization.
  • the lenses which are manufactured by the foregoing material have a water content rate of approximately 40% for properties of the material, are hydrophilic and soft to give a user less sense of a foreign matter and less pressure to the cornea when attached thereto.
  • the lenses have weak mechanical strength and have a limited oxygen permeability of approximately 10Dk[IO cm /sec](m£ O mmHg)] and a limited wearing feeling, and protein is attached thereto if a user wears them for a long time (Wilson et al., Encyclo. Of Chem. Tech., 7: 192(1976); and US patent No. 6096138).
  • the wearing feeling of the lens is closely related to the water content rate, and various attempts have been made to raise the water content rate.
  • Some of the attempts have been commercialized. Specifically, an advanced product which has a water content rate of 80% and oxygen permeability of 40Dk[IO cm /sec] (m ⁇ O mmHg)] with a water-soluble monomer such as N-vinyl-2-pyrrolidone (NVP) and N,N-dimethylacrylamide (DMA) has been developed.
  • NDP N-vinyl-2-pyrrolidone
  • DMA N,N-dimethylacrylamide
  • the soft contact lens having the high water oontent rate easily dries and has a weak material to lower optical correction performance. A user may feel inconvenient when wearing and removing the lens.
  • the contact lens having the high water content rate is mainly used as a one day disposable lens and inappropriate for long term use (Refojo. et al., Cont. & Intracular Lens Med. J.,
  • Methacrylic high molecule which includes siloxane or fluorine and is used to manufacture RGP (rigid gas permeable) contact lens provides good wearing feeling and high oxygen permeability, and affects less to the cornea and is stable even though a hard material is used. Also, methacrylic high molecule triggers side effects such as corneal edema less than conventional polymethylmethacrylate (PMMA) does.
  • siloxane or fluorine high molecule is a representative hydrophobic high molecule and is not wet by tears when applying to a contact lens. As RGB contact lens is hard and has an inherent shape, it may trigger some side effects or complications due to cornea distortion or difficulty in tear circulation. Also, the RGB contact lens has weak strength and is difficult to be manufactured, which results in high expenses and is easy to be contaminated or damaged when being worn.
  • silicone hydrogel soft contact lens including hydrogel having good oxygen permeability with silicone has been started to be manufactured.
  • Such a contact lens was released in the market for the first time in 1998, sharply increasing market share to approximately 150 million dollars in 2003 (Optician 2005).
  • Silicone hydrogel is produced as a copolymer of a hydrophilic monomer such as
  • HEMA and a silicone containing monomer General silicone monomers are very hydrophobic and difficult to maintain visibility due to separation of a phase when polymerized with a hydrophilic monomer such as HEMA
  • a compatibilizer should be developed and used to improve compatibility between hydrophilic and hydrophobic monomers.
  • PBVC poly[dimethysiloxy]di[silylbutanol] bis[vinyl carbamate]
  • a silicone macromer are used as a compatibilizer, which cost a lot of development expenses, and are difficult to manufacture lenses since they have a large molecular amount and high viscosity.
  • silicone resin is hydrophobic and limitedly used in hydrogel type lenses since it lowers a water content rate.
  • the surface should be oxygen plasma treated to be hydrophilic through a post processing to thereby prevent a problem in wearing the lenses. There arises a problem that protein adheres to the surface of the lenses.
  • Silicone hydrogel has a low elongation due to a property of the material and thus has low shape restoration of a contact lens. With increased hydrophobic property of the surface of the lens due to silicone, epithelial tissue of the cornea and the lenses are compatible with each other, and the lenses adhere to the cornea. Disclosure of Invention Technical Problem
  • a silicone hydrogel composition for a soft contact lens which includes water properly by adding N- vinyl-2-pyrrolidone (NVP>99%: Aldrich) or N,N-dimethylacrylamide (DMA, Aldrich), provides good optical transmission without a compatibilizer, and does not have a problem to be worn even without an additional surface treatment, and a soft contact lens using the same.
  • N- vinyl-2-pyrrolidone N- vinyl-2-pyrrolidone
  • DMA N,N-dimethylacrylamide
  • a silicone hydrogel composition for a soft contact lens which comprises 2-hydroxyethyl methacrylate and silicone N,O-bis(trimethylsilyl)acrylamide) monomer represented by a following chemical formula 1.
  • N,O-bis(trimethylsilyl)acrylamide) in the composition is 10 wt% and below.
  • the composition comprises ethylene glycol dimethacrylate.
  • N,O-bis(trimethylsilyl)acrylamide in the composition is 10 wt% and below, and a content of ethylene glycol dimethacrylate is 05 wt% and below.
  • the composition comprises divinyl benzene.
  • N,O-bis(trimethylsilyl)acrylamide in the composition is 10 wt% and below, and a content of divinyl benzene is 04 wt% and below.
  • the composition comprises one of N-vinyl-2-pyrrolidone and N,N-dimethylacrylamide.
  • N,O-bis(trimethylsilyl)acrylamide) is 5 wt% and below, a content of ethylene glyxtl dimethacrylate is 04 to 07 wt% and below and a content of N-vinyl-2-pyrrolidone is
  • the composition comprises N- vinyl-2-pyrrolidone.
  • N,O-bis(trimethylsilyl)acrylamide is 5 wt% and below, a content of divinyl benzene is
  • N-vinyl-2-pyrrolidone 35 wt% and below.
  • the composition comprises
  • N,O-bis(trimethylsilyl)acrylamide is 5 wt% and below, a content of ethylene glyx>l dimethacrylate is 04 wt% and below and a content of N,N-dimethylacrylamide is 40 wt% and below.
  • the composition comprises
  • N,O-bis(trimethylsilyl)acrylamide is 5 wt% and below, a content of divinyl benzene is
  • silicone hydrogel composition for a soft contact lens and a soft contact lens using the same provides a contact lens which is directly attached to the eye to correct myopia, hypermetropia and astigmatism and adjust eyesight.
  • the silicone hydrogel soft contact lens according to the present invention has hydrophilic property and high water content of 40 to 70%, high oxygen permeability of 50 to 100DK, good elongation of 200 to 400% and good optical transmission, secures healthy eyes, minimizes a sense of a foreign matter, a sense of dryness and pressure of the cornea to make a user feel comfortable. Also, the contact lens reduces rates of corneal edema or other illnesses.
  • the silicone hydrogel soft contact lens according to the present invention provides advantages of both oxygen permeable hard lens (RGP lens) having good oxygen permeability and a soft contact lens providing good wearing feeling to be wearable for consecutive two weeks to one month and tackle the problem of an existing lens being attached and detached every day.
  • RGP lens oxygen permeable hard lens
  • the present invention relates to a copolymer which is made by mixing
  • 2-hydroxyethyl methacrylate (BISOMER HEMA ULTRA made by Cognis), a hydrophilic monomer as a main material, N,O-bis(trimethylsilyl)acrylamide (self synthesis) as a silicone monomer to improve oxygen permeability, N- vinyl-2-pyrrolidone (NVP>99%, made by Aldrich) or N,N-dimethylacrylamide (DMA made by Aldrich) water soluble monomer to raise hydrophilic property and ethylene glyool dimethacrylate (EGDMA>98%, made by Aldrich) or divinyl benzene (DVB> 80%, made by Aldrich) as a cross-linking agent in small amounts and then by a thermal polymerization of 2,5-dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane) as a radical initiator.
  • a copolymer is a long molecular structure in which small units called monomers are
  • the contact lens was not particularly surface treated as it had a water content rate of
  • the contact lens is not weak and thus wearable for two weeks even though it has a high water content rate.
  • Oxygen permeability was high, 50- 100Dk ([10 (cnf/sec)(m£ O mmHg)], and had no side effects, provided comfortable feeling and caused no problem for long term wear according to many clinical tests.
  • the amount of N,O-bis(trimethylsilyl)acrylamide is increased from 1Og to 9Og by adding 1Og each, and the amount of 2-hydroxyethyl methacrylate is decreased from 9Og to 1Og by reducing 1Og each to make a mixture.
  • An initiator, 2,5-dimethyl 2,5-di(2-ethylhexanoylperoxy)hexane of QIg to Ig is dissolved to polymerize the mixture at 11O 0 C for 30 minutes.
  • an initiator of 02g (02 wt%) is used for polymerization.
  • N,O-bis(trimethylsilyl)acrylamide has high degree of crosslink, the mixture is cured without a cross-linking agent.
  • Compatibility was good with 2-hydroxyethyl methacrylate and N,O-bis(trimethylsilyl)acrylamide monomer of 1Og (10 wt%).
  • the amount of N,O-bis(trimethylsilyl)acrylamide is increased from 1Og to 9Og by adding 1Og each, and the amount of N-vinyl-2-pyrrolidone is decreased from 9Og to 1Og by reducing 1Og each to make a mixture.
  • An initiator, 2,5-dimethyl 2,5-di(2-ethylhexanoylperoxy)hexane, of QIg to Ig is dissolved to polymerize the mixture at 11O 0 C for 30 minutes.
  • the amount of N,O-bis(trimethylsilyl)acrylamide is increased from 1Og to 9Og by adding 5g each, and the amount of 2-hydroxyethyl methacrylate is decreased from 9Og to 1Og by redoing 5g each to make a mixture added with a cross-linking agent, ethylene glycol dimethacrylate, of Olg to Ig.
  • a cross-linking agent ethylene glycol dimethacrylate, of Olg to Ig.
  • An initiator, 2,5-dimethyl 2,5-di(2-ethylhexanoylperoxy)hexane of Q2g is dissolved to polymerize the mixture at HO 0 C for 30 minutes.
  • a polymer was obtained to be applicable to a lens by using ethylene glyool dimethacrylate of 05g (05 wt% and below).
  • the polymer was cured by using N,O-bis(trimethylsilyl)acrylamide of 20 wt% and below and became transparent, but water absorption was not good after hydration for N,O-bis(trimethylsilyl)acrylamide of 10 wt% to 20 wt% and below.
  • the polymer was transparently cured for 20 wt% and above, but became opaque and easily broken after hydration.
  • ethylene glycol dimethacrylate In the present polymerization, use of the cross-linking agent, ethylene glycol dimethacrylate, improved degree of cross link and transparency (compatibility) and raised curability of the polymer and strength. It can be known that ethylene glycol dimethacrylate of 05 wt% is suitable for a lens.
  • N,O-bis(trimethylsilyl)acrylamide of 10 wt% and below, 2-hydroxyethyl methacrylate of 90 wt% and above and a cross-linking agent, ethylene glyool dimethacrylate, of 05 wt% and below are polymerized, compatibility improved and the polymer was transparently cured and had good hydration, which is applicable for a flexible lens to some extent.
  • N,O-bis(trimethylsilyl)acrylamide is increased from 1Og to 9Og by adding 5g each, and the amount of 2-hydroxyethyl methacrylate is decreased from 9Og to 5g by reducing 5g each to make a mixture added with a cross-linking agent, divinyl benzene, of QIg to Ig.
  • a polymer was obtained to be applicable to a lens by using divinyl benzene of 04g (04 wt%) and below.
  • the polymer was cured by using N,O-bis(trimethylsilyl)acrylamide of 20 wt% and below and became transparent, but water absorption was not good after hydration for 10 wt% to 20 wt% and below.
  • the hydration of the polymer was good for 10 wt% and below. For 20 wt% and above, the polymer was cured transparently, but became opaque and easily broken after hydration.
  • N,O-bis(trimethylsilyl)acrylamide of 10 wt% and below, 2-hydroxyethyl methacrylate of 90 wt% and above and a cross-linking agent, divinyl benzene, of 04 wt% and below are polymerized, compatibility improves and thus a polymer which is elongated and has good transparency and water absorption can be made.
  • the polymerization is performed by adjusting a water content rate of the polymer according to the exemplary embodiment 3 to improve hydrophilic property and by adding a water soluble monomer, N-vinyl-2-pyrrolidone, to check polymerization between the materials.
  • the amount of N,O-bis(trimethylsilyl)acrylamide is increased from 5 wt% to 50 wt% by adding 5 wt% each, the amount of 2-hydroxyethyl methacrylate is decreased from 90 wt% by reducing 5 wt% each, and N-vinyl-2-pyrrolidone is increased from 5 wt% by adding 5 wt% each to make a mixture added with a cross-linking agent, ethylene glyool dimethacrylate, of Ql wt% to 1 wt%.
  • An initiator, 2,5-dimethyl 2,5-di(2-ethylhexanoylperoxy)hexane of 02 wt% is dissolved to polymerize the mixture at 110 0 C for 30 minutes.
  • the polymer was cured by using N,O-bis(trimethylsilyl)acrylamide of 5 wt% to 10 wt%, 2-hydroxyethyl methacrylate of 50 wt% and below and N-vinyl-2-pyrrolidone of 40 wt% and above are polymerized to be cured transparently.
  • N,O-bis(trimethylsilyl)acrylamide of 5 wt% to 10 wt%
  • 2-hydroxyethyl methacrylate 50 wt% and below
  • N-vinyl-2-pyrrolidone 40 wt% and above are polymerized to be cured transparently.
  • the polymer was easily broken, and lost elongation and was easily torn after hydration.
  • the polymer was cured by using N,O-bis(trimethylsilyl)acrylamide of 5 wt% and below, 2-hydroxyethyl methacrylate of 5 wt% to 90 wt% and below and N-vinyl-2-pyrrolidone of 5 wt% to 40 wt% and below are polymerized to be cured transparently.
  • the polymer using the cross-linking agent of 04 wt% to 07 wt% had good water absorption and elongation after hydration.
  • N-vinyl-2-pyrrolidone improves compatibility between materials and transparency, but increases a water oontent rate and lowers elongation and tensile strength of the polymer. If N-vinyl-2-pyrrolidone of 45 wt% and below is used, a polymer having a water content rate of 38 wt% to 55 wt% is created to appropriate for a lens since it has good elongation and wettability.
  • the polymerization is performed by adjusting a water content rate of the polymer according to the exemplary embodiment 4 to improve hydrophilb property and by adding a water soluble monomer, N-vinyl-2-pyrrolidone, to check polymerization between the materials and by using divinyl benzene to be compared with ethylene glycol dimethacrylate as the cross-linking agent a ⁇ »rding to the exemplary embodiment 5.
  • a water content rate of the polymer according to the exemplary embodiment 4 to improve hydrophilb property and by adding a water soluble monomer, N-vinyl-2-pyrrolidone, to check polymerization between the materials and by using divinyl benzene to be compared with ethylene glycol dimethacrylate as the cross-linking agent a ⁇ »rding to the exemplary embodiment 5.
  • the amount of N,O-bis(trimethylsilyl)acrylamide is increased from 5 wt% to 50 wt% by adding 5 wt% each, the amount of 2-hydroxyethyl methacrylate is decreased from 90 wt% by reducing 5 wt% each, and N-vinyl-2-pyrrolidone is increased from 5 wt% by adding 5 wt% each to make a mixture added with a cross-linking agent, divinyl benzene, of Ql wt% to 1 wt%.
  • An initiator, 2,5-dimethyl 2,5-di(2-ethylhexanoylperoxy)hexane of 02 wt% is dissolved to polymerize the mixture at 110 0 C for 30 minutes.
  • N,O-bis(trimethylsilyl)acrylamide of 5 wt% to 10 wt%, 2-hydroxyethyl methacrylate of 50 wt% to 90 wt% and below and N-vinyl-2-pyrrolidone of 10 wt% and above are polymerized to be cured transparently.
  • the polymer was easily broken, and lost elongation and was easily torn after hydration.
  • N,O-bis(trimethylsilyl)acrylamide of 5 wt% and below N,O-bis(trimethylsilyl)acrylamide of 5 wt% and below, 2-hydroxyethyl methacrylate of 5 wt% to 90 wt% and below and N- vinyl-2-pyrrolidone of 5 wt% to 40 wt% and below are polymerized to be cured transparently.
  • the polymer using the cross-linking agent of 04 wt% to 07 wt% had good water absorption and elongation after hydration.
  • N-vinyl-2-pyrrolidone improves compatibility between materials and transparency. If N-vinyl-2-pyrrolidone of 35 wt% and below is used, compatibility was good and a transparent polymer was obtained. Here, a water content rate was 38% to 55%. If N-vinyl-2-pyrrolidone of 35 wt% and above is used, a polymer having high water content rate of 55% and above was obtained.
  • N-vinyl-2-pyrrolidone improves compatibility between materials and transparency, but lowers elongation and tensile strength of the polymer due to increase in a water content rate. If N-vinyl-2-pyrrolidone of 35 wt% and below is used, a polymer has a water content rate of 38% to 55%, and provides good transparency and elongation to be appropriate for a lens.
  • the polymerization is performed by adjusting a water content rate of the polymer according to the exemplary embodiment 3 to improve hydrophilb property and by adding another water soluble monomer, N,N-dimethylacrylamide to check polymerization between the materials.
  • N,O-bis(trimethylsilyl)acrylamide of 5wt% and below according to the result from the exemplary embodiment 5 is used, the amount of 2-hydroxyethyl methacrylate is decreased from 90 wt% by reducing 5 wt% each, and the amount of N,N-dimethylacrylamide is increased from 5 wt% by adding 5 wt% each to make a mixture added with a cross-linking agent, ethylene glycol dimethacrylate, of 04 wt%.
  • An initiator, 2,5-dimethyl 2,5-di(2-ethylhexanoylperoxy)hexane of 02 wt% is dissolved to polymerize the mixture at 11O 0 C for 30 minutes.
  • N,O-bis(trimethylsilyl)acrylamide of 5 wt% and became cured to generate a transparent polymer.
  • a water oontent rate was 55% and above with a very high expansion rate.
  • Increased use of N,N-dimethylacrylamide raised the water content rate and expansion rate, and improved compatibility between the materials and transparency.
  • N,N-dimethylacrylamide improved compatibility between the materials and transparency, but triggered a very high expansion rate due to increase in the water oontent rate and lowered elongation and tensile strength of the polymer. If N,N-dimethylacrylamide of 40 wt% and above and 70 wt% and below is used, a polymer provides good transparency, water content rate and elongation to be appropriate for a lens.
  • the polymerization is performed by adjusting a water oontent rate of the polymer according to the exemplary embodiment 4 to improve hydrophilic property, to check polymerization suitability between materials and to compare with the cross-linking agent, ethylene gljcol dimethacrylate, according to the exemplary embodiment 7.
  • N,O-bis(trimethylsilyl)acrylamide of 5wt% and below according to the result from the exemplary embodiment 5 is used, the amount of 2-hydroxyethyl methacrylate is decreased from 90 wt% by reducing 5 wt% each, and the amount of N,N-dimethylacrylamide is increased from 5 wt% by adding 5 wt% each to make a mixture added with a cross-linking agent, divinyl benzene, of Q4 wt%.
  • An initiator, 2,5-dimethyl 2,5-di(2-ethylhexanoylperoxy)hexane of 02 wt% is dissolved to polymerize the mixture at 11O 0 C for 30 minutes.
  • N,O-bis(trimethylsilyl)acrylamide of 5 wt% and became cured to generate a transparent polymer.
  • a water oontent rate was 55% and above with a very high expansion rate.
  • Increased use of N,N-dimethylacrylamide raised the water content rate and expansion rate, and improved compatibility between the materials and transparency.
  • N,N-dimethylacrylamide improved compatibility between the materials and transparency, but triggered a very high expansion rate due to increase in the water content rate and lowered elongation and tensile strength of the polymer. If N,N-dimethylacrylamide of 30 wt% and above and 70 wt% and below is used, a polymer provides good transparency, water content rate and elongation to be appropriate for a lens.
  • the polymerization is performed by adjusting a water content rate of the polymer according to the exemplary embodiment 4 to improve hydrophilb property and to check polymerization suitability between two materials of N,N-dimethylacrylamide and N-vinyl-2-pyrrolidone as water soluble monomers.
  • N,O-bis(trimethylsilyl)acrylamide of 5 wt% and below according to the result from the exemplary embodiment 7 is used, 2-hydroxyethyl methacrylate of 60wt% is used and N,N-dimethylacrylamide and N-vinyl-2-pyrrolidone are changed properly within 40 wt% to make a mixture added with a cross-linking agent, ethylene glyool dimethacrylate, of 04 wt%.
  • 2,5-di(2-ethylhexanoylperoxy)hexane of 02 wt% is dissolved to polymerize the mixture at 110 0 C for 30 minutes.
  • the mixture had good compatibility and generated a transparent polymer when cured, but it changed into a milk color by hydration, regardless of changes in N,N-dimethylacrylamide and N-vinyl-2-pyrrolidone.
  • the polymer may not be used for a lens, and one of N,N-dimethylacrylamide and N- vinyl-2-pyrrolidone should be selected to use the polymer for a lens.
  • the polymerization is performed by adjusting a water content rate of the polymer according to the exemplary embodiment 5 to check polymerization suitability between two materials of N,N-dimethylacrylamide and N-vinyl-2-pyrrolidone.
  • N,O-bis(trimethylsilyl)acrylamide of 5 wt% and 2-hydroxyethyl methacrylate of 63 wt% are used and N,N-diemthylacrylamide and N-vinyl-2-pyrrolidone are changed properly within 40 wt% to make a mixture added with a cross-linking agent, divinyl benzene, of Q4 wt%.
  • An initiator, 2,5-dimethyl 2,5-di(2-ethylhexanoylperoxy)hexane of 02 wt% is dissolved to polymerize the mixture at 11O 0 C for 30 minutes.
  • the polymerization according to the present embodiment has the same result as that according to the exemplary embodiment 9.
  • the mixture had good compatibility and generated a transparent polymer when cured, but it changed into a milk color by hydration, regardless of changes in N,N-dimethylacrylamide and N- vinyl-2-pyrrolidone.
  • the polymer may not be used for a lens, and one of N,N-dimethylacrylamide and N-vinyl-2-pyrrolidone should be selected to use the polymer for a lens.
  • the polymerization according to the present embodiment has the same result as that according to the exemplary embodiment 9.
  • a soft contact lens was made by mixing 2-hydroxyethyl methacrylate, N,O-bis(trimethylsilyl)acrylamide and divinyl benzene (or ethylene glycol dimethacrylate), and N-vinyl-2-pyrrolidone or N,N-dimethylacrylamide.
  • a contact lens was made by mixing 2-hydroxyethyl methacrylate, divinyl benzene as a cross-linking agent and 2,5-dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane) as an initiator to thereby compare properties such as a water content rate, elongation rate, tensile strength and oxygen permeability.
  • the oxygen permeability is a flow rate of oxygen transmitting a unit area of a contact lens material in a unit thickness, according to a unit pressure change.
  • the method of measuring the oxygen permeability is as follows.
  • P, V and T refer to the status of the environment where the experiment is carried out.
  • P' and T' refer to STP status and V is a value calculated according to the STP status.
  • I is an average thickness of the sample
  • Pressure has a value indicated by the pressure sensor.
  • the value of the formula ® is substituted for the formula ⁇ to calculate permeability (DK).
  • the water content rate is calculated commonly by dry- weight-basis representing moisture weight ratio to a dry weight of the sample as percent, but also by wet- weight-basis representing containing moisture ratio to a total weight including moisture as percent.
  • wet- weight-basis representing containing moisture ratio to a total weight including moisture as percent.
  • there are made many definitions related to the water content rate such as "relative water content rate in saturated water content rate” or "equilibrium water content rate by relative humidity of surrounding air”.
  • volume water content rate representing containing moisture volume ratio to a total volume of the sample is also used in some cases.
  • the moisture content of the contact lens is measured by using wet- weight-basis.
  • the measuring method is as follows.
  • the mixture was then injected to a mold manufactured with polypropylene (Casting Mold) and polymerized at 11O 0 C for 30 minutes to be cured. Then, the lens was separated from the mold to check compatibility (transparency). The lens was transparent, and the water content rate and the status were measured after hydration.
  • Exemplary embodiment 12 Manufacturing of contact lens 2: [137] 2-hydroxyethyl methacrylate, N,O-bis(trimethylsilyl)acrylamide, N- vinyl-2-pyrrolidone and divinyl benzene (or ethylene gljcol dimethacrylate) [138] A mixture of 2-hydroxyethyl methacrylate of 835 wt% and above, N- vinyl-2-pyrrolidone of 15 wt% and below, N,O-bis(trimethylsilyl)acrylamide of 1 wt% and below, and divinyl benzene of 03 wt% and above (or ethylene gljcol dimethacrylate of 04 wt% and above) as a cross-linking agent is added with dissolved 2,5-dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane) of 02 wt% and above as an initiator.
  • a lens was manufactured the same as that according to the exemplary embodiment
  • Exemplary embodiment 13 Manufacturing of contact lens 3: [140] 2-hydroxyethyl methacrylate, N,O-bis(trimethylsilyl)acrylamide, N- vinyl-2-pyrrolidone and divinyl benzene (or ethylene gljcol dimethacrylate) [141] A mixture of 2-hydroxyethyl methacrylate of 71.4 wt% and above, N- vinyl-2-pyrrolidone of 25 wt% and below, N,O-bis(trimethylsilyl)acrylamide of 3 wt% and below, and divinyl benzene of 04 wt% and above (or ethylene gljcol dimethacrylate of 05 wt% and above) as a cross-linking agent is added with dissolved 2,5-dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane) of 02 wt% and above as an initiator.
  • a lens was manufactured the same as that according to the exemplary
  • Exemplary embodiment 14 Manufacturing of contact lens 4: [143] 2-hydroxyethyl methacrylate, N,O-bis(trimethylsilyl)acrylamide, N- vinyl-2-pyrrolidone and divinyl benzene (or ethylene gljcol dimethacrylate) [144] A mixture of 2-hydroxyethyl methacrylate of 643 wt% and below, N- vinyl-2-pyrrolidone of 30 wt% and above, N,O-bis(trimethylsilyl)acrylamide of 5 wt% and below, and divinyl benzene of 05 wt% and above (or ethylene glyxil dimethacrylate of 06 wt% and above) as a cross-linking agent is added with dissolved 2,5-dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane) of 02 wt% and above as an initiator.
  • a lens was manufactured the same as that according to the exemplary
  • Exemplary embodiment 15 Manufacturing of contact lens 5: [146] 2-hydroxyethyl methacrylate, N,O-bis(trimethylsilyl)acrylamide, N- vinyl-2-pyrrolidone and divinyl benzene (or ethylene glycol dimethacrylate) [147] A mixture of 2-hydroxyethyl methacrylate of 65.4 wt% and below, N- vinyl-2-pyrrolidone of 30 wt% and above, N,O-bis(trimethylsilyl)acrylamide of 4 wt% and below, and divinyl benzene of 04 wt% and above (or ethylene glycol dimethacrylate of 05 wt% and above) as a cross-linking agent is added with dissolved 2,5-dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane) of 02 wt% and above as an initiator.
  • a lens was manufactured the same as that according to the exemplary embodiment 11 to evaluate properties.
  • Exemplary embodiment 16 Manufacturing of contact lens 5: [149] 2-hydroxyethyl methacrylate, N,O-bis(trimethylsilyl)acrylamide,
  • N,N-dimethylacrylamide and divinyl benzene (or ethylene glycol dimethacrylate) [150] A mixture of 2-hydroxyethyl methacrylate of 66.4 wt% and below,
  • N,N-dimethylacrylamide of 30 wt% and above, N,O-bis(trimethylsilyl)acrylamide of Q3g, and divinyl benzene of 04 wt% and above (or ethylene glycol dimethacrylate of 05 wt% and above) as a cross-linking agent is added with dissolved 2,5-dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane) of 02 wt% and above as an initiator.
  • a lens was manufactured the same as that according to the exemplary embodiment 11 to evaluate properties.
  • Comparative embodiment 1 Manufacturing of contact lens [152] A mixture of 2-hydroxyethyl methacrylate of 9g and divinyl benzene of Ig as a cross-linking agent which are commonly used is added with dissolved 2,5-dimethyl-2,5-di(2-ethylhexanoyl peroxy)hexane) of (B2g as an initiator. The mixture was then injected to a mold manufactured with polypropylene (Casting Mold) and polymerized at 11O 0 C for 30 minutes to be cured. Then, the lens was separated from the mold to check a water content rate. According to the checking result, the lens
  • the exemplary embodiments according to the present invention are hydrophilic, and have high water content rate of 40 to 70% and high oxygen permeability of 50 to 90Dk[IO (cm /sec)(m# O mmHg)], which are far better than those according to the comparative embodiment.

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  • Health & Medical Sciences (AREA)
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  • Ophthalmology & Optometry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • Polymers & Plastics (AREA)
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Abstract

La présente invention concerne une composition d'hydrogel de silicone pour une lentille de contact souple et une lentille de contact souple qui utilise cette composition. La composition selon l'invention comprend un monomère de silicone N,O-bis(triméthylsilyl)acrylamide et du méthacrylate de 2-hydroxyéthyle ajouté avec de la N-vinyl-2-pyrrolidone hydrosoluble ou un monomère de N,N-diméthylacrylamide pour améliorer les propriétés hydrophiles et un agent de réticulation tel que le diméthacrylate d'éthylène glycol ou le divinyle benzène pour conférer des propriétés hydrophiles, une teneur en eau élevée, une perméabilité élevée à l'oxygène, un bon allongement et une bonne transmission optique.
EP07833407A 2007-06-25 2007-10-18 Composé d'hydrogel de silicone pour lentilles de contact souples et lentilles de contact souples fabriquées en utilisant le composé Withdrawn EP2170992A4 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020070061970A KR101231181B1 (ko) 2007-06-25 2007-06-25 연질 콘텍트렌즈용 실리콘 하이드로겔 조성물 및 그 조성에의해 제조된 연질 콘텍트렌즈
PCT/KR2007/005098 WO2009001987A1 (fr) 2007-06-25 2007-10-18 Composé d'hydrogel de silicone pour lentilles de contact souples et lentilles de contact souples fabriquées en utilisant le composé

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EP2170992A1 true EP2170992A1 (fr) 2010-04-07
EP2170992A4 EP2170992A4 (fr) 2010-08-04

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EP07833407A Withdrawn EP2170992A4 (fr) 2007-06-25 2007-10-18 Composé d'hydrogel de silicone pour lentilles de contact souples et lentilles de contact souples fabriquées en utilisant le composé

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JP (1) JP5432133B2 (fr)
KR (1) KR101231181B1 (fr)
CN (1) CN101688042B (fr)
AU (1) AU2007355828B2 (fr)
CA (1) CA2686938C (fr)
RU (1) RU2434899C2 (fr)
UA (1) UA92126C2 (fr)
WO (1) WO2009001987A1 (fr)

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RU2499288C2 (ru) * 2008-12-18 2013-11-20 Новартис Аг Способ изготовления силиконовых гидрогелевых контактных линз

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KR101995404B1 (ko) 2017-08-29 2019-07-02 대구가톨릭대학교산학협력단 고기능성 하이드로겔 콘택트 렌즈 조성물
KR101944717B1 (ko) * 2017-11-17 2019-02-01 주식회사 인터로조 자외선 차단 기능을 갖는 소프트 콘택트렌즈 및 이의 제조방법
CN117492228A (zh) 2017-12-13 2024-02-02 爱尔康公司 周抛和月抛水梯度接触镜片
KR102006918B1 (ko) 2017-12-21 2019-08-02 주식회사 티씨 싸이언스 실리콘 함유 소프트 콘텍트렌즈 제조방법과 상기 방법에 의해 제조된 소프트 콘텍트렌즈 및 상기 소프트 콘텍트렌즈 성형용 조성물
KR20220160733A (ko) 2021-05-28 2022-12-06 김영일 내구성과 습윤성이 양호하고 상용성이 향상되는 하이드로겔 콘택트렌즈
CN114176895B (zh) * 2021-11-23 2025-01-10 天津世纪康泰生物医学工程有限公司 一种动物用角膜保护镜
CN115128839B (zh) * 2022-08-09 2025-04-08 重庆大学 一种基于天然蚕丝制备丝素蛋白隐形眼镜的方法
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RU2499288C2 (ru) * 2008-12-18 2013-11-20 Новартис Аг Способ изготовления силиконовых гидрогелевых контактных линз
CN102382226A (zh) * 2011-08-12 2012-03-21 天津博纳艾杰尔科技有限公司 一种聚n-乙烯吡咯烷酮-二乙烯苯微球的制备方法
CN102382226B (zh) * 2011-08-12 2014-03-19 天津博纳艾杰尔科技有限公司 一种聚n-乙烯吡咯烷酮-二乙烯苯微球的制备方法

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RU2434899C2 (ru) 2011-11-27
KR101231181B1 (ko) 2013-02-07
CN101688042A (zh) 2010-03-31
KR20080113467A (ko) 2008-12-31
EP2170992A4 (fr) 2010-08-04
AU2007355828A1 (en) 2008-12-31
JP2010531474A (ja) 2010-09-24
WO2009001987A1 (fr) 2008-12-31
CA2686938A1 (fr) 2008-12-31
CN101688042B (zh) 2012-01-11
AU2007355828B2 (en) 2011-03-03
CA2686938C (fr) 2013-04-02
AU2007355828A8 (en) 2010-03-18
UA92126C2 (ru) 2010-09-27
RU2009146491A (ru) 2011-07-27

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