Classifications

• • G—PHYSICS
  • G02—OPTICS
  • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
  • G02C7/00—Optical parts
  • G02C7/02—Lenses; Lens systems ; Methods of designing lenses
  • G02C7/04—Contact lenses for the eyes
• • 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
  • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
  • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
  • C08F220/285—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
  • C08F220/286—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety and containing polyethylene oxide in the alcohol moiety, e.g. methoxy polyethylene glycol (meth)acrylate
• • 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
  • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
  • C08F230/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
• • 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
  • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
  • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
  • C08F290/06—Polymers provided for in subclass C08G
  • C08F290/062—Polyethers
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
  • C08L33/04—Homopolymers or copolymers of esters
  • C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
  • C08L51/08—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
• • G—PHYSICS
  • G02—OPTICS
  • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
  • G02C13/00—Assembling; Repairing; Cleaning
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
  • A61L12/00—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor
  • A61L12/08—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor using chemical substances
  • A61L12/14—Organic compounds not covered by groups A61L12/10 or A61L12/12
  • A61L12/141—Biguanides, e.g. chlorhexidine
  • A61L12/142—Polymeric biguanides
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L43/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium or a metal; Compositions of derivatives of such polymers
  • C08L43/02—Homopolymers or copolymers of monomers containing phosphorus

Definitions

• the present disclosure is for a soft contact lens that can provide a soft contact lens that can provide a soft contact lens that has excellent long-lasting hydrophilicity and lubricity by a simple treatment and that maintains a good wearing feeling all day. It relates to processing liquids.
• This application claims priority from Japanese Application No. 2021-177580, which is incorporated herein by reference.
• Patent Literature 1 discloses a technique of subjecting a soft contact lens to plasma treatment.
• Patent Document 2 discloses a technique of chemically bonding a soft contact lens having a reactive group and a hydrophilic polymer having a reactive group to hydrophilize the surface of the soft contact lens.
• Patent Documents 1 and 2 are intended to impart excellent hydrophilicity to the surface of the soft contact lens by subjecting the soft contact lens itself to a treatment, and although the hydrophilicity and durability are excellent, the lubricity is improved. There was room for In addition, since the surface treatment process is complicated, highly controlled manufacturing equipment is required, which is economically disadvantageous.
• Patent Documents 3 and 4 disclose techniques for imparting and enhancing hydrophilicity to the surface of soft contact lenses and improving wearing comfort by adding polyethylene glycol, cellulose-based polymers, or the like to a treatment liquid for soft contact lenses.
• Patent Document 5 discloses a technique for improving wearing comfort by adding a copolymer of a phosphorylcholine group-containing monomer and butyl methacrylate to a treatment liquid for soft contact lenses.
• An object of the present disclosure is to provide a soft contact lens treatment liquid that can easily impart hydrophilicity and lubricity to the surface of a soft contact lens and that has excellent durability.
• the treatment liquid for soft contact lenses according to the present disclosure, the surface treatment method for soft contact lenses according to the present disclosure, and the use of the copolymer (P) according to the present disclosure for producing a treatment liquid for soft contact lenses are as follows.
• R 1 and R 2 each independently represent a hydrogen atom or a methyl group.
• (meth)acrylate means “acrylate or methacrylate", and the same applies to other similar terms.
• each lower limit and upper limit can be independently combined.
• a combination of "preferable lower limit: 10” and “more preferred upper limit: 90” can be set to “10 or more and 90 or less”.
• the statement “preferably 10 to 100, more preferably 20 to 90” can be similarly changed to "10 to 90.”
• the copolymer (P) used (contained) in the treatment liquid for soft contact lenses of the present disclosure contains structural units represented by the following formulas (1a) and (1b), and the molar ratio of each structural unit is n a :n b is 10 to 90:10 to 90 (or n a :n b is 100:10 to 900), and the weight average molecular weight is 10,000 to 5,000,000.
• a structural unit means a unit of a compound contained in a polymer based on or derived from each monomer.
• the copolymer (P) used in the present disclosure has a structural unit represented by general formula (1a) below.
• the structural unit is a hydrophilic monomer represented by the following general formula (1a′), i.e., a monomer having a phosphorylcholine structure (hereinafter also referred to as “hydrophilic monomer” or “PC monomer” ) are obtained by polymerization.
• PC monomer a monomer having a phosphorylcholine structure
• R 1 represents a hydrogen atom or a methyl group.
• PC monomer is 2-((meth)acryloyloxy)ethyl 2-(trimethylammonio)ethyl phosphate, preferably 2-(methacryloyloxy)ethyl 2- (Trimethylammonio)ethyl phosphate (hereinafter also referred to as "2-methacryloyloxyethylphosphorylcholine").
• the content of the PC monomer in the copolymer (P) is 10 to 90 mol%, preferably 20 to 80 mol%, more preferably 30 to 70 mol%, still more preferably 40 ⁇ 60 mol% or 30-50 mol%. If the content is less than 10 mol%, the effect of improving the hydrophilicity of the surface of the soft contact lens cannot be expected. As the amount of the polymer decreases, the adsorption power of the copolymer (P) to the surface of the soft contact lens decreases, and the durability of the wearing feeling becomes insufficient.
• the copolymer (P) used in the present disclosure has a structural unit represented by formula (1b) below.
• the structural unit has a monomer represented by the following general formula (1b'), that is, a monomer having a polyethylene glycol structure (hereinafter also referred to as "PME monomer").
• PME monomer a monomer having a polyethylene glycol structure
• the copolymer (P) may contain a plurality of structural units represented by the following (1b) having different values of n.
• the content of the PME monomer in the copolymer (P) is 10 to 90 mol%, preferably 20 to 80 mol%, more preferably 30 to 70 mol%, still more preferably 40 ⁇ 60 mol% or 50-70 mol%.
• the copolymer (P) used in the present disclosure has the monomer represented by the formula (1b) as a structural unit, so that the adsorption power of the copolymer (P) to the surface of the soft contact lens is improved. and the durability of the feeling of wearing is improved.
• the copolymer (P) can be both hydrophilic and hydrophobic, and can be strongly adsorbed to the contact lens surface while maintaining a good effect of imparting hydrophilicity.
• the copolymer (P) may contain other monomers other than the PC monomer and the PME monomer to the extent that the effects of the present disclosure are not impaired. It is preferably composed only of the polymer.
• Linear or branched chain alkyl (meth)acrylates include, for example, methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate etc.
• Cyclic alkyl (meth)acrylates include, for example, cyclohexyl (meth)acrylate.
• aromatic group-containing (meth)acrylates include benzyl (meth)acrylate and phenoxyethyl (meth)acrylate.
• Styrenic monomers include, for example, styrene, methylstyrene and chlorostyrene.
• Examples of vinyl ether monomers include methyl vinyl ether and butyl vinyl ether.
• Vinyl ester monomers include, for example, vinyl acetate and vinyl propionate.
• Examples of hydrophilic hydroxyl group-containing (meth)acrylates include polyethylene glycol (meth)acrylate, polypropylene glycol (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate and 4-hydroxybutyl (Meth)acrylate and the like.
• Examples of acid group-containing monomers include (meth)acrylic acid, styrenesulfonic acid (meth)acryloyloxyphosphonic acid, and the like.
• Nitrogen-containing group-containing monomers include, for example, N-vinylpyrrolidone.
• the weight average molecular weight of the copolymer (P) is 10,000 to 5,000,000, preferably 11,000 or more, more preferably 12,000 or more, still more preferably 13,000 or more, and preferably is 4,000,000 or less, more preferably 3,000,000 or less, still more preferably 2,000,000 or less, even more preferably 1,500,000 or less, particularly preferably 1,000,000 or less .
• the weight average molecular weight of the copolymer (P) is 10,000 to 2,000,000, 10,000 to 1,000,000, 10,000 to 750,000, 15,000 to 750,000, 50 ,000-500,000, 100,000-500,000, 50,000-2,000,000, 100,000-2,000,000, 150,000-270,000, 13,000-1,000 , 000.
• the weight-average molecular weight is less than 10,000, the adsorptive power to the surface of the soft contact lens is reduced, and there is a possibility that the effect of the copolymer (P) on the surface of the soft contact lens cannot be expected to last. If the weight-average molecular weight exceeds 5,000,000, the viscosity may increase and handling may become difficult.
• the weight average molecular weight of the copolymer (P) is the value measured by gel permeation chromatography (GPC).
• the copolymer (P) can be prepared by copolymerizing the above monomers, and is usually a random copolymer, but an alternating copolymer in which each monomer is regularly arranged. or a block copolymer, and may partially have a graft structure.
• a copolymer ( P) can be obtained.
• the radical polymerization method can be carried out by known methods such as bulk polymerization, suspension polymerization, emulsion polymerization and solution polymerization.
• the radical polymerization method is preferably solution polymerization from the viewpoint of purification and the like.
• Purification of the copolymer (P) can be performed by known purification methods such as reprecipitation, dialysis, and ultrafiltration.
• radical polymerization initiators include azo radical polymerization initiators, organic peroxides, and persulfates.
• Azo radical polymerization initiators include, for example, 2,2'-azobis(2-diaminopropyl) dihydrochloride, 2,2'-azobis(2-(5-methyl-2-imidazolin-2-yl)propane ) dihydrochloride, 4,4′-azobis(4-cyanovaleric acid), 2,2′-azobisisobutyramide dihydrate, 2,2′-azobis(2,4-dimethylvaleronitrile), and 2,2'-azobisisobutyronitrile (AIBN) and the like.
• Organic peroxides include, for example, t-butylperoxyneodecanate, benzoyl peroxide, diisopropylperoxydicarbonate, t-butylperoxy-2-ethylhexanoate, t-butylperoxypivalate, t-butylperoxyiso butyrate, lauroyl peroxide, t-butyl peroxydecanate, succinic acid peroxide, and the like.
• persulfates include ammonium persulfate, potassium persulfate, and sodium persulfate. These radical polymerization initiators may be used alone or in combination of two or more.
• the amount of the polymerization initiator to be used is usually 0.001 to 10 parts by weight, preferably 0.02 to 5.0 parts by weight, more preferably 0.03 to 3.0 parts by weight, based on 100 parts by weight of each monomer in total. It is 0 parts by mass.
• Linear or cyclic ether solvents include, for example, ethyl cellosolve, tetrahydrofuran, and the like.
• Nitrogen-containing solvents include, for example, acetonitrile, nitromethane, N-methylpyrrolidone, and the like. Among these solvents, a mixed solvent of water and alcohol is preferred.
• the concentration of the copolymer (P) is 0.001 w/v% or more, preferably 0.002 w/v% or more, more preferably 0.003 w/v% or more. , more preferably 0.02 w/v % or more, most preferably 0.05 w/v % or more. v %, and not more than 2.0 w/v %, preferably not more than 1.5 w/v %, more preferably not more than 1.0 w/v %.
• bases include potassium hydroxide, sodium hydroxide, borax, trishydroxymethylaminomethane, monoethanolamine and the like.
• antioxidants include tocopherol acetate, dibutylhydroxytoluene and the like.
• Stabilizers include, for example, sodium edetate, glycine and the like.
• antiseptics include benzalkonium chloride, chlorhexidine gluconate, potassium sorbate, polyhexanide hydrochloride, and the like.
• the pH of the contact lens treatment liquid of the present disclosure is preferably 3.0 to 8.0, more preferably 3.5 to 7.8, and still more preferably 4.0 to 7.0, from the viewpoint of improving wearing comfort. 6, more preferably 4.5 to 7.5.
• the pH of the contact lens treatment liquid used herein refers to a value measured according to the 17th revision of the Japanese Pharmacopoeia General Test Method 2.54 pH measurement method.
• Physiological saline was prepared with reference to the literature (ISO 18369-3:2006, Ophthalmic Optics-Contact Lenses Part 3: Measurement Methods.). 8.3 g of sodium chloride, 5.993 g of sodium hydrogen phosphate dodecahydrate, and 0.528 g of sodium dihydrogen phosphate dihydrate were weighed, dissolved in water to make 1000 mL, and filtered to obtain a physiological saline solution.
• test contact lens Take out the test contact lens from the glass vial, measure the coefficient of friction in physiological saline with Nano Tribometer NTR3 (probe material: polypropylene, load: 2 mN, moving distance: 1.00 mm, speed: 0.1 mm /s) and evaluated according to the following criteria.
• ⁇ Lubricity evaluation assuming the end of wearing of soft contact lenses (1) 10 mL of physiological saline was added to a 15 mL conical tube, and one test contact lens taken out of the blister pack was immersed and shaken for 6 hours. (2) The test contact lens was taken out and sealed in a 10 mL glass vial containing 5 mL of the treatment solution for soft contact lenses of the present disclosure. (3) Sterilization was performed at 121° C.
• the contact lens treatment liquid of Example 5 was able to impart good hydrophilicity and good lubricity to the soft contact lens surface at the start of wearing and at the end of wearing. That is, the contact lens treatment liquid of Example 5 can provide a soft contact lens with a good wearing feeling for a long time due to its good hydrophilicity and lubricity and their sustainability.
• the contact lens treatment liquid of Example 6 was able to impart excellent hydrophilicity and good lubricity to the soft contact lens surface at the start of wearing and at the end of wearing. That is, the contact lens treatment liquid of Example 6 can provide a soft contact lens with a good wearing feeling for a long time due to its excellent hydrophilicity, good lubricity and durability thereof.

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• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Physics & Mathematics (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Ophthalmology & Optometry (AREA)
• General Physics & Mathematics (AREA)
• Optics & Photonics (AREA)
• General Health & Medical Sciences (AREA)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
• Eyeglasses (AREA)

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• 2022
  • 2022-10-24 WO PCT/JP2022/039425 patent/WO2023074596A1/ja not_active Ceased
  • 2022-10-24 EP EP22886923.6A patent/EP4425244A1/en active Pending
  • 2022-10-24 CN CN202280072141.7A patent/CN118202295A/zh active Pending
  • 2022-10-24 TW TW111140275A patent/TW202328421A/zh unknown
  • 2022-10-24 KR KR1020247013795A patent/KR20240089082A/ko active Pending

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