Treatment solution for soft contact lenses

Abstract

[Problem] To provide a treatment fluid for a soft contact lens that can easily provide hydrophilic and lubricating properties to a surface of a contact lens, and has superior persistence. [Solution] A treatment fluid for a soft contact lens according to the present disclosure was achieved by dissolving a copolymer in a solution at a specific concentration, said copolymer being obtained by copolymerizing at least two specific types of monomers.

Description

[Technical Field]

[0001] This disclosure relates to a processing solution for soft contact lenses that, through a simple process, imparts excellent and long-lasting hydrophilicity and lubricity to the surface of the soft contact lens, thereby providing a soft contact lens that offers a comfortable wearing experience throughout the day. This application claims priority to Japanese application No. 2021-177580, as incorporated herein by reference. [Background technology]

[0002] The comfort of wearing soft contact lenses is deeply related to the hydrophilicity and lubricity of the lens surface. To obtain soft contact lenses that provide all-day comfort, it is necessary for the lens surface to maintain high hydrophilicity and lubricity for an extended period of time. Patent Document 1 discloses a technique for applying plasma treatment to soft contact lenses. Patent Document 2 discloses a technique for hydrophilizing the surface of soft contact lenses by chemically bonding a soft contact lens having reactive groups with a hydrophilic polymer having reactive groups. Patent Documents 1 and 2 apply treatment to the soft contact lens itself to impart excellent hydrophilicity to the surface of the soft contact lens. While these methods excel in hydrophilicity and durability, there was room for improvement in lubricity. Furthermore, the complex surface treatment process necessitates highly controlled manufacturing facilities, which can be economically disadvantageous.

[0003] Patent documents 3 and 4 disclose a technology that improves the wearing comfort of soft contact lenses by adding polyethylene glycol, cellulose-based polymers, etc., to a processing solution for soft contact lenses to impart and enhance hydrophilicity to the surface of soft contact lenses.

[0004] Polymers containing phosphorylcholine analogs are known to have excellent properties such as being highly hydrophilic and highly moisturizing, possessing a phospholipid-like structure derived from biological membranes. Patent Document 5 describes a technology that improves the wearing comfort of soft contact lenses by adding a copolymer of a phosphorylcholine group-containing monomer and butyl methacrylate to a treatment solution. [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] WO2010 / 092686 [Patent Document 2] WO0001 / 074932 [Patent Document 3] WO2009 / 032122 [Patent Document 4] WO2012 / 098653 [Patent Document 5] US2009 / 0100801 [Overview of the Initiative] [Problems that the invention aims to solve]

[0006] Although contact lenses using the soft contact lens processing solutions described in Patent Documents 3, 4, and 5 offer superior wearing comfort, the copolymer does not adsorb sufficiently to the contact lens surface, resulting in only a temporary improvement in wearing comfort.

[0007] The objective of this disclosure is to provide a treatment solution for soft contact lenses that can easily impart hydrophilicity and lubricity to the surface of soft contact lenses and has excellent durability. [Means for solving the problem]

[0008] As a result of intensive studies, the inventors of the present invention have found that an excellent treatment liquid for soft contact lenses can be obtained by dissolving a copolymer obtained by copolymerizing at least two specific monomers in a solvent at a specific concentration, and the above object can be achieved, and the treatment liquid for soft contact lenses of the present disclosure has been completed.

[0009] That is, the treatment liquid for soft contact lenses according to the present disclosure, the surface treatment method of the soft contact lenses according to the present disclosure, and the use of the copolymer (P) according to the present disclosure as the production of the treatment liquid for soft contact lenses are as follows. 1. A treatment liquid for soft contact lenses containing 0.001 to 2.0 w / v% of a copolymer (P) having structural units represented by the following formulas (1a) and (1b), wherein the molar ratio n of each structural unit a :n b is 10 to 90:10 to 90, and the weight average molecular weight is 10,000 to 5,000,000. [Chemical formula] [Chemical formula] [In the above formulas (1a) and (1b), R 1 and R 2 each independently represent a hydrogen atom or a methyl group. In formula (1b), n represents 4 to 90] 2. The treatment liquid for soft contact lenses according to item 1 above, wherein the structural unit (1a) is 2-(methacryloyloxy)ethyl 2-(trimethylammonio)ethyl phosphate. 3. The treatment liquid for soft contact lenses according to item 1 or 2 above, wherein the copolymer (P) is a copolymer composed of structural units represented by formulas (1a) and (1b). 4. A method for surface treatment of a soft contact lens, including a step of bringing a solution for soft contact lenses into contact with the surface of the soft contact lens, where the solution for soft contact lenses has structural units represented by the following formulas (1a) and (1b), and the molar ratio n of each structural unit a:n b containing 0.001 to 2.0 w / v% of a copolymer (P) in which the molar ratio n Method for surface treatment of soft contact lenses. [Chemical formula] [Chemical formula] [In the above formulas (1a) and (1b), R 1 and R 2 each independently represents a hydrogen atom or a methyl group. In formula (1b), n represents 4 to 90] 5. Having structural units represented by the following formulas (1a) and (1b), and the molar ratio n a :n b is 10 to 90:10 to 90, and the weight average molecular weight is 10,000 to 5,000,000, and use of the copolymer (P) as a treatment liquid for soft contact lenses. [Chemical formula] [Chemical formula] [In the above formulas (1a) and (1b), R 1 and R 2 each independently represents a hydrogen atom or a methyl group. In formula (1b), n represents 4 to 90] [Advantages of the Invention]

[0010] It is possible to provide a treatment liquid for soft contact lenses that can impart excellent hydrophilicity, lubricity, and their persistence to soft contact lenses. [Embodiments for Carrying Out the Invention]

[0011] The treatment liquid for soft contact lenses of the present disclosure has structural units represented by the following formulas (1a) and (1b), and the molar ratio n a :nb It contains 0.001 to 2.0 w / v% copolymer (P) with a ratio of 10 to 90:10 to 90 and a weight-average molecular weight of 10,000 to 5,000,000. [ka] [ka]

[0012] In formulas (1a) and (1b) above, R 1 and R 2 Each of these independently represents either a hydrogen atom or a methyl group. In formula (1b), n represents a value between 4 and 90.

[0013] In this specification, "(meth)acrylate" means "acrylate or methacrylate," and the same applies to other similar terms. Furthermore, when preferred numerical ranges (e.g., ranges for concentration or weight-average molecular weight) are described in steps in this specification, each lower and upper limit can be combined independently. For example, in the description "preferably 10 or more, more preferably 20 or more, and preferably 100 or less, and more preferably 90 or less," the "preferred lower limit: 10" and the "more preferred upper limit: 90" can be combined to get "10 or more and 90 or less." Similarly, in the description "preferably 10 to 100, more preferably 20 to 90," the range can be changed to "10 to 90."

[0014] In this specification, "soft contact lens processing solution" (in particular, "soft contact lens shipping solution") refers to a solution that is sealed in a packaging container such as a blister package along with the soft contact lenses when they are distributed. Generally, soft contact lenses are used in a swollen state with an aqueous solution, so the lenses are sealed in a packaging container in a swollen state with the aqueous solution at the time of shipment from the factory so that they can be used immediately.

[0015] <Copolymer (P)> The copolymer (P) used (included) in the processing solution for soft contact lenses of this disclosure comprises constituent units represented by the following formulas (1a) and (1b), and the molar ratio n of each constituent unit a :n b 10~90:10~90 (or, n a :n b The ratio is 100:10~900, and the weight-average molecular weight is 10,000~5,000,000. A constituent unit refers to a compound unit contained in a polymer based on or derived from each monomer.

[0016] [ka] [ka]

[0017] In formulas (1a) and (1b) above, R 1 and R 2 Each of these independently represents either a hydrogen atom or a methyl group. In formula (1b), n represents a value between 4 and 90.

[0018] [Monomer represented by formula (1a)] The copolymer (P) used in this disclosure has a constituent unit represented by the following general formula (1a). This constituent unit is obtained by polymerizing a hydrophilic monomer represented by the following general formula (1a'), that is, a monomer having a phosphorylcholine structure (hereinafter also referred to as "hydrophilic monomer" or "PC monomer"). By including the PC monomer as a constituent unit in the copolymer (P), hydrophilicity can be imparted to soft contact lenses.

[0019] [ka] [ka]

[0020] In equations (1a) and (1a') above, R 1This indicates a hydrogen atom or a methyl group.

[0021] The PC monomer is 2-((meth)acryloyloxy)ethyl 2-(trimethylammonio)ethyl phosphate, preferably 2-(methacryloyloxy)ethyl 2-(trimethylammonio)ethyl phosphate represented by the following formula (1a'') (hereinafter also referred to as "2-methacryloyloxyethyl phosphorylcholine").

[0022] [ka]

[0023] The PC monomer content in the copolymer (P) is 10 to 90 mol%, preferably 20 to 80 mol%, more preferably 30 to 70 mol%, and even more preferably 40 to 60 mol% or 30 to 50 mol%. If the content is less than 10 mol%, the effect of improving the hydrophilicity to the soft contact lens surface cannot be expected, and if the content is greater than 90 mol%, the amount of monomer represented by formula (1b) becomes relatively small, the adsorption force of the copolymer (P) to the soft contact lens surface decreases, and the duration of wearing comfort becomes insufficient.

[0024] [Monomer represented by formula (1b)] The copolymer (P) used in this disclosure has a structural unit represented by the following formula (1b). This 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"). By including the PME monomer in the copolymer (P), the resulting soft contact lens will have a sustained good wearing comfort. Furthermore, the copolymer (P) may include a plurality of constituent units represented by (1b) below, each having a different value of n.

[0025] [ka] [ka]

[0026] In the above formulas (1b) and (1b'), R 2 The symbol represents a hydrogen atom or a methyl group. n = 4 to 90.

[0027] The PME monomer content in the copolymer (P) is 10 to 90 mol%, preferably 20 to 80 mol%, more preferably 30 to 70 mol%, and even more preferably 40 to 60 mol% or 50 to 70 mol%. As described above, since the copolymer (P) used in this disclosure has monomers represented by formula (1b) as constituent units, the adsorption force of the copolymer (P) to the soft contact lens surface can be improved, resulting in good durability of wearing comfort.

[0028] In formula (1b) above, n = 4 to 90, preferably n = 9 to 60, more preferably n = 9 to 30, and even more preferably n = 20 to 30. If n is less than 4, the adsorption force of the copolymer (P) to the soft contact lens surface decreases, and if it is greater than 90, the cohesive force between copolymers (P) increases, resulting in a deterioration of the transparency of the resulting soft contact lens treatment solution and contact lenses.

[0029] The copolymer (P) can achieve both hydrophilic and hydrophobic properties, allowing it to strongly adsorb to the contact lens surface while maintaining a good hydrophilic effect.

[0030] [Other monomers] The copolymer (P) may contain other monomers other than the PC monomer and PME monomer, to the extent that it does not impair the effects of the present disclosure, but it is preferable that it consists only of the PC monomer and PME monomer.

[0031] Other monomers include polymerizable monomers selected from, for example, linear or branched alkyl (meth)acrylates, cyclic alkyl (meth)acrylates, aromatic group-containing (meth)acrylates, styrene monomers, vinyl ether monomers, vinyl ester monomers, hydrophilic hydroxyl group-containing (meth)acrylates, acid group-containing monomers, and nitrogen group-containing monomers.

[0032] Examples of linear or branched alkyl (meth)acrylates include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, lauryl (meth)acrylate, and stearyl (meth)acrylate. Examples of cyclic alkyl (meth)acrylates include cyclohexyl (meth)acrylate. Examples of aromatic group-containing (meth)acrylates include benzyl (meth)acrylate and phenoxyethyl (meth)acrylate. Examples of styrene monomers include styrene, methylstyrene, and chlorostyrene. Examples of vinyl ether monomers include methyl vinyl ether and butyl vinyl ether. Examples of vinyl ester monomers include 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. Examples of acid group-containing monomers include (meth)acrylic acid, styrene sulfonic acid, and (meth)acryloyloxyphosphonic acid. Examples of nitrogen-containing monomers include N-vinylpyrrolidone.

[0033] When the copolymer (P) contains other monomers as constituent units, the number of moles of PC monomers (n a ), PME monomer (number of moles: n b ), and other monomers (number of moles: n x The molar ratio of each constituent unit based on ) is n a :n b :n x It is preferable that the ratios are 10-50:10-80:10-50.

[0034] [Weight-average molecular weight of copolymer (P)] The weight-average molecular weight of copolymer (P) is 10,000 to 5,000,000, preferably 11,000 or more, more preferably 12,000 or more, even more preferably 13,000 or more, preferably 4,000,000 or less, more preferably 3,000,000 or less, even more preferably 2,000,000 or less, even more preferably 1,500,000 or less, and particularly preferably 1,000,000 or less. For example, the weight-average molecular weight of copolymer(P) may be 10,000-2,000,000, 10,000-1,000,000, 10,000-750,000, 15,000-750,000, 50,000-500,000, 100,000-500,000, 50,000-2,000,000, 100,000-2,000,000, 150,000-270,000, or 13,000-1,000,000. If the weight-average molecular weight is less than 10,000, the adsorption force to the soft contact lens surface will decrease, and the sustained effect of the copolymer (P) on the soft contact lens surface may not be achieved. If the weight-average molecular weight exceeds 5,000,000, the viscosity may increase, making it difficult to handle.

[0035] The weight-average molecular weight of a copolymer (P) is the value obtained by gel permeation chromatography (GPC).

[0036] [Method for producing copolymer (P)] The copolymer (P) can be prepared by copolymerizing the monomers, and is usually a random copolymer, but may also be an alternating copolymer or a block copolymer in which each monomer is regularly arranged, and may have a graft structure in part.

[0037] Specifically, for example, a copolymer (P) can be obtained by radical polymerization of a mixture of the monomers in the presence of a radical polymerization initiator under an inert gas atmosphere such as nitrogen, carbon dioxide, argon, and helium. Radical polymerization can be carried out by known methods such as bulk polymerization, suspension polymerization, emulsion polymerization, and solution polymerization. Solution polymerization is preferred as the radical polymerization method from the viewpoint of purification. The copolymer (P) can be purified by known purification methods such as reprecipitation, dialysis, and ultrafiltration.

[0038] Examples of radical polymerization initiators include azo radical polymerization initiators, organic oxides, and persulfur oxides. Examples of azo radical polymerization initiators include 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'-azobisisobutylamide dihydrate, 2,2'-azobis(2,4-dimethylvaleronitrile), and 2,2'-azobisisobutyronitrile (AIBN). Examples of organic oxides include t-butyl peroxyneodecanate, benzoyl peroxide, diisopropyl peroxydicarbonate, t-butyl peroxy-2-ethylhexanoate, t-butyl peroxypivalate, t-butyl peroxyisobutyrate, lauroyl peroxide, t-butyl peroxydecanate, and succinate peroxide. Examples of persulfur oxides include ammonium persulfate, potassium persulfate, and sodium persulfate. These radical polymerization initiators may be used individually or in combination of two or more. The amount of polymerization initiator used is typically 0.001 to 10 parts by mass, preferably 0.02 to 5.0 parts by mass, and more preferably 0.03 to 3.0 parts by mass, per 100 parts by mass of the total of each monomer.

[0039] The copolymer (P) can be synthesized in the presence of a solvent. The solvent is not particularly limited as long as it dissolves each monomer composition and does not adversely affect the reaction. Examples include water, alcohol-based solvents, ketone-based solvents, ester-based solvents, linear or cyclic ether-based solvents, and nitrogen-containing solvents. Examples of alcohol-based solvents include methanol, ethanol, n-propanol, and isopropanol. Examples of ketone solvents include acetone, methyl ethyl ketone, and diethyl ketone. An example of an ester solvent is ethyl acetate. Examples of linear or cyclic ether solvents include ethyl cellosolve and tetrahydrofuran. Examples of nitrogen-containing solvents include acetonitrile, nitromethane, and N-methylpyrrolidone. Among these solvents, a mixed solvent of water and alcohol is preferred.

[0040] [Concentration of copolymer (P)] The processing solution for soft contact lenses of this disclosure has a copolymer (P) concentration of 0.001 w / v% or more, preferably 0.002 w / v% or more, more preferably 0.003 w / v% or more, even more preferably 0.02 w / v% or more, and most preferably 0.05 w / v%. / The concentration is v%, and is 2.0 w / v% or less, preferably 1.5 w / v% or less, and more preferably 1.0 w / v% or less. If the copolymer (P) concentration is less than 0.001 w / v%, the amount of copolymer (P) added is insufficient, resulting in contact lenses that do not provide good wearing comfort and its long-lasting effect. If it exceeds 2.0 w / v%, aseptic filtration during manufacturing may become difficult.

[0041] In this disclosure, "w / v%" refers to the mass of a component in 100 mL of solution, expressed in grams (g). For example, "the processing solution of this disclosure contains 1.0 w / v% copolymer (P)" means that 100 mL of the solution contains 1.0 g of copolymer (P). As the solvent used in the processing solution of this disclosure, water, methanol, ethanol, n-propanol, isopropanol, or other alcohols or mixtures thereof can be used. The water used in the contact lens processing solution of this disclosure can be water that is typically used in the manufacture of pharmaceuticals and medical devices. Specifically, ion-exchanged water, purified water, sterile purified water, distilled water, and water for injection can be used.

[0042] [Other ingredients] In addition to the polymer (P), the contact lens treatment solution disclosed herein may contain other components as needed, such as vitamins, amino acids, sugars, viscosity modifiers, cooling agents, inorganic salts, organic acid salts, acids, bases, antioxidants, stabilizers, and preservatives. Examples of vitamins include flavin adenine dinucleotide sodium, cyanocobalamin, retinyl acetate, retinyl palmitate, pyridoxine hydrochloride, panthenol, sodium pantothenate, and calcium pantothenate. Examples of amino acids include aspartic acid or its salts, and aminoethylsulfonic acid. Examples of sugars include glucose, mannitol, sorbitol, xylitol, and trehalose. Examples of viscosity-concentrating agents include hydroxypropylmethylcellulose. vinegar Examples include hydroxyethylcellulose. Examples of cooling agents include menthol and camphor. Examples of inorganic salts include sodium chloride, potassium chloride, sodium hydrogen phosphate, and anhydrous sodium dihydrogen phosphate. Examples of organic acid salts include sodium citrate. Examples of acids include phosphoric acid, citric acid, sulfuric acid, acetic acid, hydrochloric acid, and boric acid. Examples of bases include potassium hydroxide, sodium hydroxide, borax, trishydroxymethylaminomethane, and monoethanolamine. Examples of antioxidants include tocopherol acetate and dibutylhydroxytoluene. Examples of stabilizers include sodium edetate and glycine. Examples of preservatives include benzalkonium chloride, chlorhexidine gluconate, potassium sorbate, and polyhexanide hydrochloride.

[0043] [pH of contact lens treatment solution] The pH of the contact lens treatment solution of this disclosure is preferably 3.0 to 8.0, more preferably 3.5 to 7.8, even more preferably 4.0 to 7.6, and even more preferably 4.5 to 7.5, from the viewpoint of improving wearing comfort. In this specification, the pH of the contact lens treatment solution refers to the value measured according to the pH measurement method in accordance with the 17th edition of the Japanese Pharmacopoeia, General Test Methods 2.54.

[0044] [Osmotic pressure and osmotic pressure ratio of contact lens treatment solution] The osmotic pressure of the contact lens treatment solution disclosed herein is preferably 200 mOsm to 400 mOsm, more preferably 225 mOsm to 375 mOsm, even more preferably 230 mOsm to 350 mOsm, and even more preferably 240 mOsm to 340 mOsm, from the viewpoint of improving wearing comfort. The osmotic pressure ratio is preferably 0.7 to 1.4, more preferably 0.7 to 1.3, and even more preferably 0.8 to 1.2. In this specification, the osmotic pressure of the contact lens treatment solution refers to the value measured according to the osmotic pressure measurement method (osmolality measurement method) of General Test Methods 2.47 of the 17th edition of the Japanese Pharmacopoeia, and the osmotic pressure ratio refers to the value obtained by dividing the obtained osmotic pressure by the osmotic pressure of 0.9 mass% physiological saline solution (286 mOsm).

[0045] [Method for manufacturing a treatment solution for soft contact lenses] The soft contact lens treatment solution disclosed herein can be manufactured by a general method for manufacturing contact lens solutions. For example, it can be manufactured by mixing and stirring a polymer (P), a solvent and other components as needed. The resulting soft contact lens treatment solution may be subjected to sterile filtration or other operations as needed.

[0046] [Surface treatment method for soft contact lenses] One embodiment of the present disclosure also relates to a surface treatment method for soft contact lenses, which includes a step of bringing the soft contact lens solution of the present disclosure into contact with the surface of the soft contact lens. The contact may include, but is not limited to, immersing the soft contact lens in the soft contact lens solution of the present disclosure or spraying the soft contact lens solution of the present disclosure onto the surface of the soft contact lens.

[0047] [Use of copolymer (P) in the manufacture of soft contact lens solutions] One embodiment of the present disclosure also includes the use of the copolymer (P) described above as a means of manufacturing the soft contact lens solution of the present disclosure.

[0048] (Example of the composition of the processing solution for soft contact lenses in this disclosure) The following are examples, but are not limited to, of the combinations of constituent units of the copolymer (P) contained in the processing solution for soft contact lenses of this disclosure. Constituent units represented by formula (1a): Constituent units represented by formula (1b): Other monomers 2-Methacryloyloxyethyl phosphorylcholine (MPC): Equation (1b) for n=9~30 2-Methacryloyloxyethyl phosphorylcholine (MPC): Formula (1b) for n=9~30: one or more other monomers selected from butyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, (meth)acrylic acid and N-vinylpyrrolidone 2-Methacryloyloxyethyl phosphorylcholine (MPC): Equation (1b) for n=20~30 2-Methacryloyloxyethyl phosphorylcholine (MPC): Formula (1b) for n=20-30: one or more other monomers selected from butyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, (meth)acrylic acid and N-vinylpyrrolidone In addition, the constituent units represented by formula (1a), formula (1b), and other monomers in each of the above combinations may be replaced with constituent units from other combinations to constitute the copolymer (P) contained in the soft contact lens processing solution of this disclosure. [Examples]

[0049] The soft contact lens solutions of this disclosure will be described in more detail below with reference to examples and comparative examples, but this disclosure is not limited thereto. The copolymers used in the examples and comparative examples are as follows.

[0050] <Copolymer (P)> In the examples, copolymers 1 to 4 shown below were used as the polymers for implementation.

[0051] MPC: 2-Methacryloyloxyethyl phosphorylcholine (product of NOF Corporation) PME-400: Methoxy polyethylene glycol methacrylate (n≒9, product of NOF Corporation) PME-1000: Methoxy polyethylene glycol methacrylate (n ≈ 23, product of NOF Corporation) PME-4000: Methoxy polyethylene glycol methacrylate (n ≈ 90, product of NOF Corporation)

[0052] The obtained copolymer (1 mg) was dissolved in purified water (1 g) and measured. Other measurement conditions are as follows. Column: SB-802.5HQ + SB-806MN HQ Mobile phase: 20 mM phosphate buffer (pH 7.0) Standard substance: polyethylene glycol / oxide Measuring instrument: HLC-8320GPC (manufactured by Tosoh Corporation) Method for calculating weight-average molecular weight: Molecular weight calculation program (EcoSEC Date Analysis) Flow rate: 0.5 mL per minute Injection volume: 100μL Column oven: 45℃ Measurement time: 70 minutes

[0053] Copolymer 1: MPC / PME-1000 copolymer (molar ratio = 30 / 70, weight-average molecular weight: 253,000)

[0054] Copolymer 2: MPC / PME-1000 copolymer (molar ratio = 50 / 50, weight-average molecular weight: 202,000)

[0055] Copolymer 3: MPC / PME-400 / PME-1000 copolymer (molar ratio = 30 / 20 / 50, weight-average molecular weight: 195,000)

[0056] Copolymer 4: MPC / PME-4000 copolymer (molar ratio = 80 / 20, weight-average molecular weight: 170,000)

[0057] <Comparative polymer> In the comparative example, the following homopolymers were used as comparative polymers: homopolymer 1, homopolymer 2, comparative copolymer, and PVP K90.

[0058] Homopolymer 1: MPC homopolymer (weight-average molecular weight: 300,000)

[0059] Homopolymer 2: PME-1000 homopolymer (weight-average molecular weight: 84,000)

[0060] Comparative copolymer: MPC / 2-hydroxyethyl methacrylate copolymer (molar ratio = 50 / 50, weight-average molecular weight: 356,000)

[0061] PVP K90: Polyvinylpyrrolidone K90

[0062] <Test contact lenses used for evaluation> Lens A: One Day Fine UV Plus soft contact lens (product of Seed Co., Ltd.) Lens B: Menicon 1-Day soft contact lenses (a product of Menicon Co., Ltd.)

[0063] <Preparation of physiological saline solution> Physiological saline solution was prepared based on the reference (ISO 18369-3:2006, Ophthalmic Optics-Contact Lenses Part3: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 out, dissolved in water to make 1000 mL, and filtered to obtain physiological saline solution.

[0064] <Preparation of treatment solution for soft contact lenses> The copolymer was dissolved in a predetermined amount of physiological saline to prepare the polymer solution shown in Table 1 below. Furthermore, the polymer solution and physiological saline were mixed to prepare the contact lens treatment solution shown in Table 1 below.

[0065] <Hydrophilicity Evaluation> In the examples and comparative examples, the surface hydrophilicity of the soft contact lenses was evaluated according to the following procedure. 〇 Evaluation of surface hydrophilicity, simulating the initial wear of soft contact lenses. (1) Add 10 mL of physiological saline to a 15 mL conical tube, immerse one test contact lens removed from the blister pack, and shake for 6 hours. (2) The test contact lens was removed and sealed in a 10 mL glass vial to which 5 mL of the soft contact lens processing solution of the present disclosure was added. (3) Sterilized at 121°C for 20 minutes. (4) The test contact lenses were removed from the glass vials, and the time until the water film on the lens surface was broken (BUT) was measured with a stopwatch and evaluated according to the following criteria. 〇 Evaluation of surface hydrophilicity of soft contact lenses, assuming the end of wear. (1) Add 10 mL of physiological saline to a 15 mL conical tube, immerse one test contact lens removed from the blister pack, and shake for 6 hours. (2) The test contact lens was removed and sealed in a 10 mL glass vial to which 5 mL of the soft contact lens processing solution of the present disclosure was added. (3) Sterilized at 121°C for 20 minutes. (4) Add 10 mL of physiological saline to a 15 mL conical tube, immerse one test contact lens removed from the glass vial, and shake for 6 hours. (5) The test contact lenses were removed from the conical tubes, and the time until the water film on the lens surface broke off (BUT) was measured with a stopwatch and evaluated according to the following criteria. 3 points: 15 seconds or more 2 points: 10 seconds or more, less than 15 seconds 1 point: 5 seconds or more, less than 10 seconds 0 points: Less than 5 seconds

[0066] <Lubricity Evaluation> In the examples and comparative examples, the lubricity of the contact lenses was evaluated according to the following procedure. Lubricity evaluation simulating the initial wear of soft contact lenses. (1) Add 10 mL of physiological saline to a 15 mL conical tube, immerse one test contact lens removed from the blister pack, and shake for 6 hours. (2) The test contact lens was removed and sealed in a 10 mL glass vial to which 5 mL of the soft contact lens processing solution of the present disclosure was added. (3) Sterilized at 121°C for 20 minutes. (4) The test contact lenses were removed from the glass vials, and the coefficient of friction in physiological saline solution was measured using a nanotribometer NTR3 (probe material: polypropylene, load: 2mN, travel distance: 1.00mm, speed: 0.1mm / s), and evaluated according to the following criteria. Lubricity evaluation simulating the end of soft contact lens wear. (1) Add 10 mL of physiological saline to a 15 mL conical tube, immerse one test contact lens removed from the blister pack, and shake for 6 hours. (2) The test contact lens was removed and sealed in a 10 mL glass vial to which 5 mL of the soft contact lens processing solution of the present disclosure was added. (3) Sterilized at 121°C for 20 minutes. (4) Add 10 mL of physiological saline to a 15 mL conical tube, immerse one test contact lens removed from the glass vial, and shake for 6 hours. (5) The test contact lenses were removed from the conical tubes, and the coefficient of friction was measured using a nanotribometer NTR3 (probe material: polypropylene, load: 2mN, travel distance: 1.00mm, speed: 0.1mm / s), and evaluated according to the following criteria. 3 points: Less than 0.50 2 points: 0.50 or higher, less than 1.0 1 point: 1.0 or higher, less than 1.5 0 points: 1.5 or higher

[0067] <Sustainability Assessment> In the examples and comparative examples, the durability was evaluated based on the hydrophilicity and lubricity evaluation results, according to the following criteria. +++: In both evaluations, the scores for the initial and final estimated wear times are the same. ++: In either evaluation, the score for the initial and final assessments decreased by 1 point. +: In both evaluations, the scores for both the initial and final assessments decreased by 1 point. —: In any evaluation, the score at the start of wear decreased by 2 points or more compared to the score at the end of wear.

[0068] <Wearing comfort evaluation> Regarding the examples and comparative examples, the wearing comfort was evaluated based on the following criteria, using the evaluation results of hydrophilicity and lubricity assumed at the end of wearing. Excellent wearing comfort: Hydrophilicity: 3, Lubricity: 3 Comfortable to wear: Hydrophilicity: 2, Lubricity: 3 : Hydrophilicity: 3, Lubricity: 2 : Hydrophilicity: 2, Lubricity: 2 Unsatisfactory wearing comfort: Other than the above

[0069] <Example 1> 100 mL of physiological saline was measured, 1 g of copolymer 1 was added, and the mixture was stirred to dissolve it (this is the polymer solution). 10 mL of the polymer solution was taken out, and the total volume was increased to 100 mL using physiological saline. The solution was then sterile filtered to obtain the treatment solution for soft contact lenses. The hydrophilicity, lubricity, and durability of test contact lenses treated with this soft contact lens treatment solution were evaluated. The evaluation results are shown in Table 1 below.

[0070] <Examples 2-5> The hydrophilicity, lubricity, and durability of test contact lenses treated with a contact lens treatment solution prepared according to the same procedure as in Example 1, except that the types and amounts of components shown in Table 1 below were used, were evaluated. The evaluation results are shown in Table 1 below.

[0071] <Comparative Examples 1-4> The hydrophilicity, lubricity, and durability of test contact lenses treated with a contact lens treatment solution prepared according to the same procedure as in Example 1, except that the types and amounts of components shown in Table 2 below were used, were evaluated. The evaluation results are shown in Table 2 below.

[0072] <Rating> The contact lens treatment solutions of Examples 1-3 were able to impart excellent hydrophilicity and lubricity to the surface of soft contact lenses, both under simulated conditions at the start and end of wear. In other words, the contact lens treatment solutions of Examples 1-3 and 5, with their excellent hydrophilicity and lubricity and their persistence, can provide soft contact lenses with excellent comfort for extended periods. The contact lens treatment solution of Example 4 was able to impart good hydrophilicity and good lubricity to the surface of the soft contact lens, both under simulated conditions at the start and end of wear. In other words, the contact lens treatment solution of Example 4 can provide soft contact lenses with good long-term comfort due to its good hydrophilicity and lubricity and their persistence. The contact lens treatment solution of Example 5 was able to impart good hydrophilicity and good lubricity to the surface of the soft contact lens, both under simulated conditions at the start and end of wear. In other words, the contact lens treatment solution of Example 5 can provide soft contact lenses with good long-term comfort due to its good hydrophilicity and lubricity and their persistence. The contact lens treatment solution of Example 6 was able to impart excellent hydrophilicity and good lubricity to the surface of the soft contact lens, both under simulated conditions at the start and end of wear. In other words, the contact lens treatment solution of Example 6 can provide soft contact lenses with a comfortable wearing experience for extended periods due to its excellent hydrophilicity, good lubricity, and the persistence of these properties. The contact lens treatment solution in Comparative Example 1 had significantly inferior durability and provided an unsatisfactory wearing experience. The contact lens treatment solution in Comparative Example 2 did not provide sufficient comfort when worn. The contact lens treatment solution in Comparative Example 3 had significantly inferior durability and provided an unsatisfactory wearing experience. The contact lens treatment solution in Comparative Example 4 had significantly inferior durability and provided an unsatisfactory wearing experience.

[0073] [Table 1]

[0074] [Table 2] [Industrial applicability]

[0075] By using the soft contact lens processing solution disclosed herein with soft contact lenses, it is possible to provide soft contact lenses with excellent wearing comfort throughout the day.

Claims

1. It has constituent units represented by the following formulas (1a) and (1b), and the molar ratio n of each constituent unit ａ :n ｂ A treatment solution for soft contact lenses containing 0.001 to 2.0 w / v% of a copolymer (P) having a ratio of 10 to 90:10 to 90 and a weight-average molecular weight of 10,000 to 5,000,000. 【Chemistry 1】 【Chemistry 2】 [In formulas (1a) and (1b) above, R １ and R ２ Each of these independently represents either a hydrogen atom or a methyl group. In formula (1b), n represents 4 to 90.

2. The treatment solution for soft contact lenses according to claim 1, wherein the constituent unit (1a) is 2-(methacryloyloxy)ethyl 2-(trimethylammonio)ethyl phosphate.

3. The processing solution for soft contact lenses according to claim 1 or 2, wherein the copolymer (P) is a copolymer consisting of structural units represented by formulas (1a) and (1b).

4. The treatment solution for soft contact lenses according to Claim 1, wherein the constituent unit (1a) is 2-(methacryloyloxy)ethyl 2-(trimethylammonio)ethyl phosphate, and the constituent unit (1b) is methoxypolyethylene glycol methacrylate.

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