Soft contact lens solution

Abstract

[Problem] To provide a soft contact lens solution that imparts, to a soft contact lens, surface hydrophilicity, lubricity, and lipid-adhesion-suppressing ability. [Solution] It was found that said problem can be solved by a solution containing a buffer and two specific copolymers, resulting in the completion of a soft contact lens according to the present disclosure.

Description

[Technical Field]

[0001] The present disclosure relates to a solution for soft contact lenses that imparts surface hydrophilicity, lubricity, and lipid adhesion inhibitory properties to soft contact lenses. This application claims priority from Japanese Application No. 2021-107493, which is incorporated herein by reference. [Background technology]

[0002] Due to their ease and convenience, the number of contact lens wearers has increased rapidly, and they have now become a commonly used medical device. However, many patients stop wearing contact lenses due to discomfort, and research into improving contact lens comfort is still insufficient. It is known that this discomfort is closely related to wettability and antifouling properties, and there is a need for methods to improve the hydrophilicity of contact lens surfaces, impart antifouling properties, etc. In recent years, the coefficient of friction of contact lens surfaces has also become important, and contact lenses with a high coefficient of friction can not only cause discomfort when worn, but can also cause conjunctivitis and other conditions (see Non-Patent Documents 1 and 2).

[0003] To solve the above problems, methods for surface treatment of contact lenses have been developed. For example, a method has been disclosed in which a hydrophilic monomer is graft-polymerized onto the surface of a plasma-treated contact lens to impart hydrophilicity and antifouling properties to the surface (Patent Document 1). Another method has been disclosed for producing contact lenses that are highly hydrophilic and lubricating by coating the surface of the contact lens with a polymer (Patent Document 2). However, these surface treatments require complicated steps, which is undesirable for mass production. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Patent Publication No. 2018-022174 [Patent Document 2] Patent Publication No. 6-122779 [Non-patent literature]

[0005] [Non-Patent Document 1] Roba, M., 2011, Friction Measurements on Contacct Lenses In Their Operating Environment, Tribol. Lett., 44(3), 387-397. [Non-patent document 2] Yokoi, Norihiko, 2009, Mechanism of dry eye sensation when wearing soft contact lenses, Journal of the Japanese Contact Lens Society, 51, S33-S35 Summary of the Invention [Problem to be solved by the invention]

[0006] The present invention aims to provide a solution for soft contact lenses that imparts surface hydrophilicity, lubricity, and lipid adhesion inhibitory properties to soft contact lenses. [Means for solving the problem]

[0007] As a result of intensive research to solve the above problems, the inventors discovered that a solution containing two specific copolymers and a buffer agent can solve the above problems, and have completed the solution for soft contact lenses of the present disclosure.

[0008] 1. 0.001 to 1.0 w / v% of a copolymer (P) containing structural units represented by formulas (1a) to (1c), in which the ratio of the numbers of the structural units, na:nb:nc, is 100:10 to 400:2 to 50, and the weight average molecular weight is 5,000 to 2,000,000; 0.002 to 2.0 w / v% of a copolymer (Q) which is a polyoxyethylene-polyoxypropylene block copolymer, the number of moles of ethylene oxide (EO) added being 120 to 200, the number of moles of propylene oxide (PO) added being 10 to 70, and the EO content being 60 to 90 wt%; and a buffering agent; A soft contact lens solution containing [ka] [ka] [ka] (In the formula, R 1 , R 2 and R 5 R each independently represents a hydrogen atom or a methyl group. 3 and R 4 R each independently represents a hydrogen atom, a methyl group, an ethyl group, or combines with each other to form a morpholino group. 6 represents a monovalent hydrocarbon group having 12 to 24 carbon atoms. 2. A solution for soft contact lenses according to the preceding item 1, wherein the buffer is a phosphate buffer solution. 3. A solution for soft contact lenses according to the preceding item 1 or 2, wherein the structural unit represented by formula (1a) is a structural unit based on 2-(methacryloyloxy)ethyl 2-(trimethylammonio)ethyl phosphate, the structural unit represented by formula (1b) is a structural unit based on N,N-dimethylacrylamide, and the structural unit represented by formula (1c) is a structural unit based on stearyl methacrylate. 4. A solution for soft contact lenses according to the preceding item 1 or 2, wherein the structural unit represented by formula (1a) is a structural unit based on 2-(methacryloyloxy)ethyl 2-(trimethylammonio)ethyl phosphate, the structural unit represented by formula (1b) is a structural unit based on N,N-dimethylacrylamide, and the structural unit represented by formula (1c) is a structural unit based on lauryl methacrylate. 5. A method for treating the surface of a soft contact lens, comprising: a step of contacting a soft contact lens solution with the surface of a soft contact lens, The soft contact lens solution comprises: 0.001 to 1.0 w / v% of a copolymer (P) containing structural units represented by formulas (1a) to (1c), wherein the ratio of the numbers of the structural units, na:nb:nc, is 100:10 to 400:2 to 50 and the weight average molecular weight is 5,000 to 2,000,000; 0.002 to 2.0 w / v% of a copolymer (Q) which is a polyoxyethylene-polyoxypropylene block copolymer, the number of moles of ethylene oxide (EO) added being 120 to 200, the number of moles of propylene oxide (PO) added being 10 to 70, and the EO content being 60 to 90 wt%; and and a buffering agent, A method for treating the surface of soft contact lenses. [ka] [ka] [ka] (In the formula, R 1 , R 2 and R 5 R each independently represents a hydrogen atom or a methyl group. 3 and R 4 R each independently represents a hydrogen atom, a methyl group, an ethyl group, or combines with each other to form a morpholino group. 6 represents a monovalent hydrocarbon group having 12 to 24 carbon atoms. 6. A copolymer (P) containing structural units represented by formulas (1a) to (1c), in which the ratio of the numbers of the structural units, na:nb:nc, is 100:10 to 400:2 to 50, and the weight average molecular weight is 5,000 to 2,000,000; A copolymer (Q) which is a polyoxyethylene-polyoxypropylene block copolymer, in which the number of moles of ethylene oxide (EO) added is 120 to 200, the number of moles of propylene oxide (PO) added is 10 to 70, and the EO content is 60 to 90 wt %; and 1. Use of a buffer in the manufacture of a solution for soft contact lenses. [ka] [ka] [ka] (In the formula, R 1 , R 2 and R 5 R each independently represents a hydrogen atom or a methyl group. 3 and R 4 R each independently represents a hydrogen atom, a methyl group, an ethyl group, or combines with each other to form a morpholino group. 6 represents a monovalent hydrocarbon group having 12 to 24 carbon atoms. [Effects of the Invention]

[0009] The solution for soft contact lenses of the present disclosure can impart surface hydrophilicity, lubricity, and lipid adhesion inhibitory properties to soft contact lenses. DETAILED DESCRIPTION OF THE INVENTION

[0010] The soft contact lens solution of the present disclosure comprises: 0.001 to 1.0 w / v% of a copolymer (P) containing structural units represented by general formulas (1a) to (1c), wherein the ratio of the numbers of the structural units, na:nb:nc, is 100:10 to 400:2 to 50 and the weight average molecular weight is 5,000 to 2,000,000; 0.002 to 2.0 w / v% of a copolymer (Q) which is a polyoxyethylene-polyoxypropylene block copolymer, the number of moles of ethylene oxide (EO) added being 120 to 200, the number of moles of propylene oxide (PO) added being 10 to 70, and the EO content being 60 to 90 wt%; and a buffering agent; Contains.

[0011] [ka]

[0012] [ka]

[0013] [ka]

[0014] R 1 , R 2 and R 5 R each independently represents a hydrogen atom or a methyl group. 3 and R 4 R each independently represents a hydrogen atom, a methyl group, an ethyl group, or combines with each other to form a morpholino group. 6 represents a monovalent hydrocarbon group having 12 to 24 carbon atoms. The composition of the solution for soft contact lenses of the present disclosure will be described below.

[0015] In this specification, "(meth)acrylate" means "acrylate or methacrylate," and the same applies to other similar terms. Furthermore, in this specification, when preferred numerical ranges (e.g., ranges of concentration or weight-average molecular weight) are described in stages, the respective lower and upper limits can be independently combined. For example, in the description "preferably 10 or more, more preferably 20 or more, and preferably 100 or less, more preferably 90 or less," the "preferable lower limit: 10" and the "more preferable upper limit: 90" can be combined to form "10 or more and 90 or less." Furthermore, in the description "preferably 10 to 100, more preferably 20 to 90," the "10 to 90" can be similarly expressed.

[0016] <Copolymer (P)> The copolymer (P) contains structural units represented by general formulas (1a) to (1c), in which the ratio of the numbers of the structural units, na:nb:nc, is 100:10 to 400:2 to 50, and the weight average molecular weight is 5,000 to 2,000,000. The structural unit means a unit of a compound contained in a polymer based on or derived from each monomer.

[0017] [Constituent unit represented by general formula (1a)] Copolymer (P) teeth, Copolymer (P) has a structural unit having a phosphorylcholine structure represented by the following formula (1a) (hereinafter also referred to as a "PC structural unit"): By including the PC structural unit, copolymer (P) has hydrophilicity, and can impart lubricity and lipid adhesion inhibitory properties to contact lenses.

[0018] [ka]

[0019] Above R 1 represents a hydrogen atom or a methyl group.

[0020] The copolymer (P) having the PC structural unit can be obtained, for example, by copolymerizing a phosphorylcholine group-containing monomer (hereinafter also referred to as "PC monomer") represented by the following general formula (1a'):

[0021] [ka]

[0022] From the viewpoint of availability, the PC monomer is preferably 2-((meth)acryloyloxy)ethyl-2-(trimethylammonio)ethyl phosphate, and more preferably 2-(methacryloyloxy)ethyl-2-(trimethylammonio)ethyl phosphate (hereinafter also referred to as "2-methacryloyloxyethyl phosphorylcholine") represented by the following formula (1a''):

[0023] [ka]

[0024] PC monomers can be produced by known methods. For example, the method disclosed in JP-A-54-63025 can be referenced. One example of such a method involves reacting a hydroxyl-containing polymerizable monomer with 2-bromoethylphosphoryl dichloride in the presence of a tertiary base, and then reacting the resulting compound with a tertiary amine. Another example of such a method is the method disclosed in JP-A-58-154591. Another example of such a method involves reacting a hydroxyl-containing polymerizable monomer with a cyclic phosphorus compound to obtain a cyclic compound, which is then subjected to a ring-opening reaction with a tertiary amine.

[0025] [Constituent unit represented by general formula (1b)] The copolymer (P) has a structural unit (hereinafter also referred to as an "amide structural unit") represented by the following general formula (1b): The presence of the amide structural unit in the copolymer (P) can improve the adhesion of the copolymer (P) to contact lenses.

[0026] [ka]

[0027] In the above formula (1b), R 2 represents a hydrogen atom or a methyl group, and R 3 and R 4 each independently represents a hydrogen atom, a methyl group, an ethyl group, or combines with each other to form a morpholino group. n is the number of amide units b Regarding the number of PC components, n a When is set to 100, n b / n a The ratio is 10 to 400 / 100, preferably 30 to 250 / 100. n b If the size is too large, the biocompatibility will be insufficient, and if it is too small, it will not be possible to achieve the desired effect on the contact lens.

[0028] The amide constitutional units in the copolymer (P) are obtained from (meth)acrylamide or a (meth)acrylamide derivative, which is a monomer represented by the following formula (1b') used during polymerization of the copolymer (P).

[0029] [ka]

[0030] R in formula (1b') 2 , R 3 and R 4 are R in formula (1b), respectively. 2 , R 3 and R 4 is the same as Examples of (meth)acrylamide or (meth)acrylamide derivatives represented by the above formula (1b') include N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, and N-acryloylmorpholine. A preferred amide structural unit is N,N-dimethylacrylamide.

[0031] [Constituent unit represented by general formula (1c)] Copolymer (P) has a structural unit represented by the following general formula (1c) (hereinafter also referred to as a "hydrophobic structural unit"): The hydrophobic structural unit in copolymer (P) is introduced to enhance adsorption to contact lenses and impart a desired effect to the contact lenses.

[0032] [ka]

[0033] In the above formula (1c), R 5 represents a hydrogen atom or a methyl group, and R 6 represents a monovalent hydrocarbon group having 12 to 24, 12 to 22, or 12 to 18 carbon atoms. R 6 The alkyl group may be either linear or branched, but is preferably linear. Specific examples include lauryl, stearyl, and behenyl groups. Number of hydrophobic units, n c Regarding the number of PC components, n a When is set to 100, n c / n a The ratio is 2 to 50 / 100, preferably 5 to 25 / 100. n c If n is too large, the hydrophilicity of the copolymer (P) decreases, which may reduce its solubility in aqueous solutions, making it difficult to prepare a contact lens solution. c If the value is too small, the ability to form a physically crosslinked gel through hydrophobic interactions will decrease, the adhesion to the contact lens surface will decrease, and the intended effect on the contact lens may not be sustained. The hydrophobic structural unit in the copolymer (P) is obtained from a hydrophobic monomer represented by the following formula (1c') used during polymerization of the copolymer (P).

[0034] [ka]

[0035] R in formula (1c') 5 and R 6 are R in formula (1c), respectively. 5 and R 6 is the same as Examples of the hydrophobic monomer represented by formula (1c') include linear alkyl (meth)acrylates such as lauryl (meth)acrylate, stearyl (meth)acrylate, and behenyl (meth)acrylate. Preferred hydrophobic structural units include stearyl methacrylate and lauryl methacrylate.

[0036] [Other structural units] Copolymer (P) used in the soft contact lens solution of the present disclosure can also incorporate structural units other than those represented by formulas (1a) to (1c) within the range that does not impair the effects of the solution. When the following other polymerizable monomers (other structural units) are blended into the monomer composition used to synthesize copolymer (P), the blending ratio can be appropriately selected within the range that does not affect the effects of the solution. For example, n represented by the above formula (1a) constituting copolymer (P) a When the molar ratio is taken as 100, the molar ratio is preferably 50 or less.

[0037] Other polymerizable monomers that can be used in the synthesis of the copolymer (P) include, for example, linear or branched alkyl (meth)acrylates, cyclic alkyl (meth)acrylates, aromatic group-containing (meth)acrylates, styrene-based monomers, vinyl ether monomers, vinyl ester monomers, hydrophilic hydroxyl group-containing (meth)acrylates, acid group-containing monomers, nitrogen-containing group-containing monomers, amino group-containing monomers, and cationic group-containing monomers. Examples of linear or branched alkyl(meth)acrylates include methyl(meth)acrylate, ethyl(meth)acrylate, butyl(meth)acrylate, and 2-ethylhexyl(meth)acrylate. Examples of cyclic alkyl(meth)acrylates include cyclohexyl(meth)acrylate. Examples of aromatic-containing (meth)acrylates include benzyl (meth)acrylate and phenoxyethyl (meth)acrylate. Examples of the styrene-based monomer include styrene, methylstyrene, and chloromethylstyrene. Examples of the vinyl ether monomer include methyl vinyl ether, butyl vinyl ether, diethylene glycol monovinyl ether, and ethylene glycol monovinyl 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, 4-hydroxybutyl (meth)acrylate, and 2-hydroxypropyl (meth)acrylate. Examples of the acid group-containing monomer include (meth)acrylic acid, styrenesulfonic acid, and (meth)acryloyloxyphosphonic acid. Examples of the nitrogen-containing group-containing monomer include N-vinylpyrrolidone, N-vinylacetamide, and N-methyl-N-vinylacetamide. Examples of the amino group-containing monomer include aminoethyl (meth)acrylate, dimethylaminoethyl (meth)acrylate, and N,N-dimethylaminopropyl (meth)acrylamide. Examples of the cationic group-containing monomer include 2-hydroxy-3-(meth)acryloyloxypropyltrimethylammonium chloride.

[0038] [Molecular weight of copolymer (P)] The copolymer (P) used in the soft contact lens solution of the present disclosure is a polymer having a weight-average molecular weight of 5,000 to 2,000,000, and preferably 100,000 to 1,500,000. If the weight-average molecular weight is less than 5,000, the copolymer may not be able to sufficiently adsorb to the contact lens surface, and the desired effects (surface hydrophilicity, lubricity, and lipid adhesion inhibitory ability) may not be achieved, while if it exceeds 2,000,000, the sterile filtration required for producing the contact lens solution may become difficult.

[0039] [Method for synthesizing copolymer (P)] The copolymer (P) used in the soft contact lens solution of the present disclosure can be obtained by radical polymerization of the above-mentioned monomer blend. The copolymer (P) can be synthesized, for example, by radically polymerizing the above-mentioned monomer composition in the presence of a radical polymerization initiator under an inert gas-substituted or inert gas atmosphere such as nitrogen, carbon dioxide, argon, or helium. Radical polymerization can be carried out by known methods such as bulk polymerization, suspension polymerization, emulsion polymerization, and solution polymerization. Of the radical polymerization methods, solution polymerization is preferred from the standpoint of purification, etc. The copolymer (P) can be purified by known purification methods such as reprecipitation, dialysis, and ultrafiltration.

[0040] Examples of the radical polymerization initiator include an azo-based radical polymerization initiator, an organic peroxide, and a persulfate. Examples of the azo radical polymerization initiator 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 peroxides include t-butyl peroxyneodecanate, benzoyl peroxide, diisopropyl peroxydicarbonate, t-butyl peroxy-2-ethylhexanoate, t-butyl peroxypivalate, t-butyl peroxydiisobutyrate, lauroyl peroxide, t-butyl peroxydecanoate, and succinic acid peroxide (=succinyl peroxide). Examples of persulfate include ammonium persulfate, potassium persulfate, and sodium persulfate. These radical polymerization initiators can be used alone or in combination of two or more. The amount of the polymerization initiator used is usually 0.001 to 10 parts by mass, preferably 0.01 to 5.0 parts by mass, per 100 parts by mass of the monomer composition.

[0041] The synthesis of the copolymer (P) can be carried out in the presence of a solvent. The solvent may be any solvent that dissolves the monomer composition and does not react with it, such as water, alcohol solvents, ketone solvents, ester solvents, linear or cyclic ether solvents, and nitrogen-containing solvents. Preferably, water, alcohol, or a mixture thereof is used. Examples of alcohol solvents include methanol, ethanol, n-propanol, and isopropanol. Examples of the ketone solvent include acetone, methyl ethyl ketone, and diethyl ketone. Examples of ester solvents include ethyl acetate. Examples of the linear or cyclic ether solvent include ethyl cellosolve and tetrahydrofuran. Examples of nitrogen-containing solvents include acetonitrile, nitromethane, and N-methylpyrrolidone.

[0042] <Copolymer Q> The copolymer (Q) used in the solution for soft contact lenses of the present disclosure is a polyoxyethylene-polyoxypropylene block copolymer, in which the number of moles of ethylene oxide (EO) added is 120 to 200, the number of moles of propylene oxide (PO) added is 10 to 70, and the content of EO is 60 to 90. wt% is. Examples of polyoxyethylene-polyoxypropylene block copolymers include polyoxyethylene-polyoxypropylene-polyoxyethylene triblock copolymers and polyoxypropylene-polyoxyethylene-polyoxypropylene triblock copolymers, with polyoxyethylene-polyoxypropylene-polyoxyethylene triblock copolymers being preferred. The number of moles of ethylene oxide (EO) added in copolymer (Q) is preferably in the range of 120 to 200, more preferably 140 to 180. The number of moles of propylene oxide (PO) added in copolymer (Q) is preferably in the range of 10 to 70, more preferably 20 to 40. The ranges (preferred ranges, more preferred ranges, etc.) of the number of moles of ethylene oxide (EO) added and the number of moles of propylene oxide (PO) added can be combined or changed. For example, the number of moles of ethylene oxide (EO) added can be selected within a preferred range, and the number of moles of propylene oxide (PO) added can be selected within a more preferred range. If these moles are too small, copolymer (Q) becomes too small and may penetrate into the contact lens, causing deformation. If the number of moles is too large, the viscosity of the contact lens solution increases, potentially making sterile filtration difficult. The EO content in copolymer (Q) is preferably 60 to 90 wt%, more preferably 70 to 80 wt%. If the EO content is less than 60 wt%, it becomes difficult to impart sufficient effects (particularly surface hydrophilicity and lubricity) to contact lenses, while if it exceeds 90 wt%, there is a risk that the adsorption to contact lenses will decrease.

[0043] <Buffering agent> The buffer used in the soft contact lens solution of the present disclosure can be one that can be used in general contact lens solutions, etc. Specific examples include hydrochloric acid, acetic acid, citric acid, sodium hydroxide, boric acid, borates (borax, etc.), phosphates (monosodium phosphate, disodium phosphate, monopotassium phosphate, dipotassium phosphate, etc.), citrates (sodium citrate, etc.), tris(hydroxymethyl)aminomethane, and hydrates thereof, and it is preferable to use two or more of these. The phosphate buffer used in the soft contact lens solution of the present disclosure is not particularly limited as long as it is a buffer that dissolves in the soft contact lens solution to contain phosphoric acid (phosphate ions), but is preferably a buffer containing monosodium phosphate and disodium phosphate or hydrates thereof. The concentration of the buffering agent is 0.01 to 1.5 w / v%, and more preferably 0.05 to 1.0 w / v%. A concentration of less than 0.01 w / v% results in low buffering capacity, making it difficult to control the pH, while a concentration of more than 1.5 w / v% is undesirable because it impairs the solubility of other components. Furthermore, from the viewpoints of reducing irritation when wearing contact lenses and improving wearing comfort, the buffering agent is preferably blended in at an appropriate ratio so that the pH of the contact lens solution is 3 to 9, and more preferably 4 to 8. In this specification, the pH of the contact lens solution refers to the value measured in accordance with the pH measurement method in General Test Method 2.54 of the 17th Edition of the Japanese Pharmacopoeia.

[0044] <Composition of the solution for soft contact lenses of the present disclosure> The solution for soft contact lenses of the present disclosure can be obtained by dissolving 0.001 to 1.0 w / v % of copolymer (P), 0.002 to 2.0 w / v % of copolymer (Q), and a buffer in water or a mixed solution of water and an alcohol such as ethanol, n-propanol, or isopropanol. By including copolymer (P), copolymer (Q) and a buffer in the soft contact lens solution, lubricity, hydrophilicity and lipid adhesion inhibitory properties can be imparted to the contact lens, thereby providing a comfortable wearing experience to the contact lens wearer.

[0045] In addition to the copolymer (P) and the copolymer (Q), the soft contact lens solution of the present disclosure may contain, as needed, isotonic agents, vitamins, amino acids, sugars, thickening agents, cooling agents, inorganic salts, antioxidants, stabilizers, preservatives, and the like that can be used in general contact lens solutions. The amount of these components other than the copolymer (P) and the copolymer (Q) to be added is not particularly limited, but is preferably 0.01 to 5.0 w / v%, more preferably 0.05 to 4.0 w / v%, and even more preferably 0.1 to 3.0 w / v%.

[0046] Examples of isotonic agents include sodium chloride. Examples of vitamins include flavin adenine dinucleotide sodium, cyanocobalamin, retinol acetate, retinol palmitate, pyridoxine hydrochloride, panthenol, sodium pantothenate, calcium pantothenate, and the like. 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 thickening agents include hydroxypropylmethylcellulose and hydroxyethylcellulose. Examples of the cooling agent include menthol and camphor. Examples of inorganic salts include sodium chloride, potassium chloride, and anhydrous sodium dihydrogen phosphate. Examples of antioxidants include tocopherol acetate, sodium hydrogen sulfite, sodium sulfite, ascorbic acid, and dibutylhydroxytoluene. Examples of stabilizers include sodium edetate and glycine. Examples of preservatives include benzalkonium chloride, chlorhexidine gluconate, potassium sorbate, and polyhexanide hydrochloride.

[0047] <Product Form of the Soft Contact Lens Solution of the Present Disclosure> Specific product forms of the soft contact lens solution of the present disclosure include the following. Specific examples include contact lens shipping solutions, contact lens care products, contact lens storage solutions, contact lens cleaning solutions, and contact lens cleaning and storage solutions. In this specification, contact lens shipping solutions refer to solutions in which contact lenses are immersed before shipping. In this specification, soft contact lens care products are not particularly limited as long as they are solutions used in the care of soft contact lens products, and include, for example, disinfecting solutions, cleaning solutions, storage solutions, cleaning and storage solutions, disinfecting and cleaning and storage solutions, and wearing solutions for soft contact lenses.

[0048] (Configuration example of contact lens solution of the present disclosure) Examples of combinations of the constituent units of the copolymer (P) contained in the contact lens solution of the present disclosure are shown below, but are not limited thereto. Structural unit represented by formula (1a): Structural unit represented by formula (1b): Structural unit represented by formula (1c) 2-(Methacryloyloxy)ethyl 2-(trimethylammonio)ethyl phosphate:N,N-dimethylacrylamide:Stearyl methacrylate 2-(Methacryloyloxy)ethyl 2-(trimethylammonio)ethyl phosphate:N,N-dimethylacrylamide:Lauryl methacrylate In addition, the constitutional unit represented by formula (1a), the constitutional unit represented by formula (1b), and the constitutional unit represented by formula (1c) in each of the above combinations may be replaced with constitutional units in other combinations to form the copolymer (P) contained in the contact lens solution of the present disclosure.

[0049] (Surface treatment method for soft contact lenses according to the present disclosure) One embodiment of the present disclosure is also directed to a method for treating the surface of a soft contact lens, comprising the step of bringing the above-described solution for soft contact lenses of the present invention into contact with the surface of the soft contact lens. Examples of contacting include, but are not limited to, immersing the soft contact lens in the solution for soft contact lenses of the present disclosure, or spraying the solution for soft contact lenses of the present disclosure onto the surface of the soft contact lens.

[0050] (Use of the copolymer (P), copolymer (Q) and buffer of the present disclosure in the production of a solution for soft contact lenses) One embodiment of the present disclosure is also directed to the use of the above-described copolymer (P), copolymer (Q), and buffering agent in the production of the soft contact lens solution of the present disclosure.

[0051] Hereinafter, the solution for soft contact lenses of the present disclosure will be described in more detail with reference to examples and comparative examples, but the solution for soft contact lenses of the present disclosure is not limited to these.

[0052] <Copolymer (P)> As the copolymer (P), the following copolymers (P1) to (P4) were used. In this example, the weight average molecular weight of the copolymer (P) was measured by dissolving 5 mg of each copolymer obtained in a methanol / chloroform mixture (80:20) to prepare a sample solution. The analytical conditions were as follows: Column: PLgel-mixed-C Standard substance: polyethylene glycol Detector: Differential refractometer RI-8020 (manufactured by Tosoh Corporation) Calculation method for weight average molecular weight: Molecular weight calculation program (GPC program for SC-8020) Flow rate: 1 mL per minute Injection volume: 100μL Column oven: constant temperature around 40°C

[0053] [Copolymer (P1)] A copolymer using 2-(methacryloyloxy)ethyl 2-(trimethylammonio)ethyl phosphate represented by general formula (1a") as a PC monomer (PC building block), N,N-dimethylacrylamide as an amide monomer (amide building block), and stearyl methacrylate as a hydrophobic monomer (hydrophobic building block) as building blocks. Ratio of the number of constituent units: [(1a) / (1b) / (1c)] = 100 / 90 / 10 Weight average molecular weight: 1,000,000 [Copolymer (P2)] A copolymer using 2-(methacryloyloxy)ethyl 2-(trimethylammonio)ethyl phosphate represented by general formula (1a") as a PC monomer, N,N-dimethylacrylamide as an amide monomer, and stearyl methacrylate as a hydrophobic monomer as building blocks. Ratio of the number of constituent units: [(1a) / (1b) / (1c)] = 100 / 223 / 10 Weight average molecular weight: 1,200,000 [Copolymer (P3)] A copolymer using 2-(methacryloyloxy)ethyl 2-(trimethylammonio)ethyl phosphate represented by general formula (1a") as a PC monomer, N,N-dimethylacrylamide as an amide monomer, and stearyl methacrylate as a hydrophobic monomer as building blocks. Ratio of the number of constituent units: [(1a) / (1b) / (1c)] = 100 / 34 / 9 Weight average molecular weight: 700,000 [Copolymer (P4)] A copolymer using 2-(methacryloyloxy)ethyl 2-(trimethylammonio)ethyl phosphate represented by general formula (1a") as a PC monomer, N,N-dimethylacrylamide as an amide monomer, and lauryl methacrylate as a hydrophobic monomer as building blocks. Ratio of the number of constituent units: [(1a) / (1b) / (1c)] = 100 / 90 / 20 Weight average molecular weight: 1,000,000

[0054] <Comparative polymer for copolymer (P)> The following polymers (A) to (C) were used as comparative polymers for copolymer (P). [Polymer (A)] 2-Methacryloyloxyethyl phosphorylcholine homopolymer (weight average molecular weight 200,000) obtained by the method described in the examples of JP-A-8-333421 [Polymer (B)] Commercially available N,N-dimethylacrylamide homopolymer (Sigma-Aldrich Japan, product name: Poly(N,N-dimethylacrylamide), DDMAT Terminated, number-average molecular weight: 10,000) [Polymer (C)] Commercially available lauryl methacrylate homopolymer (Sigma-Aldrich Japan, product name: Polylauryl methacrylate, weight-average molecular weight: 470,000)

[0055] <Copolymer (Q)> As the copolymer (Q), the following copolymers (Q1) to (Q3) were used. [Copolymer (Q1)] Commercially available polyoxyethylene-polyoxypropylene-polyoxyethylene block copolymer (NOF Pronon) (登録商標) 188P (product name), EO added mole number 160, PO added mole number 30, EO content 80wt%) [Copolymer (Q2)] Commercially available polyoxyethylene-polyoxypropylene-polyoxyethylene block copolymer (NOF Pronon) (登録商標) 208 (product name), EO added mole number 150, PO added mole number 35, EO content 80wt%) [Copolymer (Q3)] Commercially available polyoxyethylene-polyoxypropylene-polyoxyethylene block copolymer (NOF Unilube) (登録商標) 70DP-950B (product name), EO added mole number 200, PO added mole number 70, EO content 70wt%)

[0056] <Comparative polymer for copolymer (Q)> The following polymers (D) to (E) were used as comparative polymers for copolymer (Q). [Polymer (D)] Commercially available ethylene glycol homopolymer (Sigma-Aldrich Polyethylene Glycol 10000 (product name), weight-average molecular weight 9,000) [Polymer (E)] Commercially available propylene glycol homopolymer (Alfa Aesar's Polypropylene Glycol 4,000 (product name), weight-average molecular weight 4,000)

[0057] <Preparation of contact lens solution> Example 1 Approximately 80 g of purified water was weighed out, and 0.01 g of copolymer (P1), 0.02 g of copolymer (Q1), and 0.83 g of sodium chloride, 0.599 g of sodium hydrogen phosphate dodecahydrate, and 0.053 g of sodium dihydrogen phosphate dihydrate were dissolved therein to make a total volume of 100 mL. This was filtered to obtain a sterile contact lens solution. The appearance and properties of the contact lens solution of Example 1 are shown in Table 1. [Examples 2 to 15] Sterile contact lens solutions were prepared in the same manner as in Example 1, except that the types and amounts of ingredients shown in Tables 1 and 2 were used. The appearance and properties of the contact lens solutions of each Example are shown in Tables 1 and 2. [Comparative Examples 1 to 5] Sterile contact lens solutions were prepared in the same manner as in Example 1, except that the types and amounts of ingredients shown in Table 3 were used. The appearance and properties of the contact lens solutions of each Comparative Example are shown in Table 3.

[0058] [Table 1]

[0059] [Table 2]

[0060] [Table 3]

[0061] Sodium chloride: Otsuka Pharmaceutical Co., Ltd. Sodium hydrogen phosphate dodecahydrate: Fujifilm Wako Pure Chemical Industries, Ltd. Sodium dihydrogen phosphate dihydrate: Fujifilm Wako Pure Chemical Industries, Ltd. Boric acid: Fujifilm Wako Pure Chemical Industries Borax: Fujifilm Wako Pure Chemical Industries Purified water: Kenei Pharmaceutical

[0062] <Confirmation of the effect of contact lens solution on improving the lubricity of contact lenses> The improvement in lubricity of contact lenses by the contact lens solutions of the Examples and Comparative Examples was evaluated according to the following procedure. (登録商標) (manufactured by Menicon) was used. (procedure) 1) The contact lens solution of Example 1 was prepared. 2) One contact lens was removed from the blister pack and placed in a 15 mL centrifuge tube. 3) 10 mL of ISO physiological saline was added to the centrifuge tube from 2) and shaken overnight. 4) After shaking in 3), the ISO saline solution was removed and 10 mL of the contact lens solution prepared in 1) was added. 5) Autoclave treatment was carried out at 121°C for 20 minutes. 6) After cooling to room temperature, the contact lens was removed and placed on the index finger to evaluate its lubricity, simulating the start of wearing the contact lens. 7) After 6), the contact lens was immersed once in the solution prepared in 1), the water film on the surface of the contact lens was wiped off, and the lens was placed on the index finger to evaluate the lubricity simulating wearing the contact lens. (ISO saline composition) Sodium chloride 8.3g Sodium hydrogen phosphate dodecahydrate 0.528g Sodium dihydrogen phosphate dihydrate 0.528g Ion-exchanged water, total volume 100 mL (ISO18369-3:2006, Ophthalmic Optics-Contact Lenses Part3:Measurement Methods)

[0063] Lubricity was evaluated on a scale of 1 to 10, with 10 being the "best lubricity" and 1 being the "no lubricity at all." A value of 6.0 or higher was considered to have "excellent surface lubricity," and a value of 8.5 or higher was considered to have "particularly excellent surface lubricity." The contact lens solutions of Examples 2 to 15 and Comparative Examples 1 to 5 were also evaluated according to the above procedure.

[0064] <Confirmation of the effect of contact lens solution on improving the hydrophilicity of contact lens surfaces> The improvement in the hydrophilicity of the contact lens surface by the contact lens solutions of the Examples and Comparative Examples was evaluated according to the following procedure. Menicon 1Day (registered trademark) (manufactured by Menicon) was used to evaluate the effect of improving the hydrophilicity of the contact lens surface.

[0065] (procedure) 1) The same procedures as 1) to 5) described in <Confirmation of the effect of improving the surface lubricity of contact lenses> were carried out. 2) The contact lenses were removed, and the time until the water film on the lens surface disappeared (BUT) was measured with a stopwatch. This was used to evaluate the surface hydrophilicity at the time of starting contact lens wear. 3) Another contact lens was immersed in 2 mL of ISO physiological saline and shaken for 6 hours. 4) After 6 hours, the contact lenses were removed and the BUT was measured with a stopwatch. This was used to evaluate the surface hydrophilicity of the contact lenses while they were being worn. Those with a BUT of 10 seconds or more were rated as "excellent surface hydrophilicity," and those with a BUT of 15 seconds or more were rated as "particularly excellent surface hydrophilicity." The contact lens solutions of Examples 2 to 15 and Comparative Examples 1 to 5 were also evaluated according to the above procedure.

[0066] <Confirmation of the effect of contact lens solution in improving the ability to inhibit lipid adhesion to contact lenses> The ability of the contact lens solutions of the Examples and Comparative Examples to inhibit lipid adhesion to contact lenses was evaluated according to the following procedure. CLARITI 1Day (registered trademark) (manufactured by CooperVision) was used to examine the effect of improving the ability to inhibit lipid adhesion to contact lenses.

[0067] (procedure) Preparation of artificial eye discharge 1) 0.5 g of the lipid mixture shown below was mixed with 100 mL of the phosphate-borate buffer solution shown below. 2) The mixture was suspended at 60°C using a homomixer. 3) The pH was adjusted to 7.0 with 1N hydrochloric acid. (Composition of mixed lipids) Oleic acid 0.06g Linolenic acid 0.06g Palmitic acid 0.06g Tripalmitic acid 0.81g Cetyl alcohol 0.20g Cetyl myristate 0.81g Cholesterol 0.08g Cholesterol palmitate 0.08g Lecithin (derived from eggs) 2.83g (Composition of phosphate-borate buffer solution) Sodium chloride 2.25g Potassium dihydrogen phosphate 1.25g Sodium tetraborate decahydrate 5.65g Ion-exchanged water: make the total volume 250 mL Reference: Kaoru Iwai, Mari Moriyama, Masaki Imayasu, Hidenari Tanaka: Study on lipid adhesion to contact lenses, Nihon Colle Magazine, 37, 58-61, 1995

[0068] (evaluation) 1) The same procedures as 1) to 5) described in <Confirmation of the effect of improving the surface lubricity of contact lenses> were carried out. 2) After the contact lenses were cooled to room temperature, they were immersed in 4 mL of artificial eye lubricant per contact lens for 4 hours. 3) The contact lenses were removed, lightly rinsed with the ISO physiological saline solution shown above, and then dried. 4) The contact lens was immersed in 3 mL of extraction solution (ethanol / diethyl ether = 1 / 1 (v / v)). 5) Sonication was carried out for 10 minutes. 6) 2 mL of the extract was placed in a test tube and the solvent was evaporated at 90°C. 7) 0.4 g of concentrated sulfuric acid was added to the test tube from 6) and heated at 90°C for 15 minutes. 8) After cooling the test tube in 7) to room temperature, 2.5 mL of the vanillin solution shown below was added. 9) After keeping the mixture at 37°C for 10 minutes, the absorbance at 540 nm was measured. (vanillin solution) Vanillin 0.12g 20mL of ion-exchanged water Phosphoric acid 80mL The amount of lipid adhesion to the contact lens was calculated by comparing the obtained absorbance with a calibration curve. The lipid adhesion inhibition rate was calculated based on the amount of lipid adhesion when a similar experiment was performed using ISO physiological saline as a control solution for the contact lens solution. A lipid adhesion inhibition rate of 10% or more was considered to have "adhesion inhibition ability," and a rate of over 15% was considered to have "excellent adhesion inhibition ability." The contact lens solutions of Examples 2 to 15 and Comparative Examples 1 to 5 were also evaluated according to the above procedure.

[0069] <Each evaluation result> (Improves the lubricity of contact lens surfaces) The surface lubricity of the contact lenses treated with the contact lens solutions of Examples 1-15 was excellent or the best at the beginning and during wear. In particular, the surface lubricity of the contact lenses treated with the contact lens solution of Example 4 was the best at the beginning and during wear. Furthermore, it was confirmed that the contact lens solutions do not cause deformation of the contact lenses. On the other hand, no improvement in the surface lubricity of the contact lens treated with the contact lens solution of Comparative Example 1-5 could be confirmed. As a result, the contact lens solutions of Examples 1-15 can impart excellent (durable) surface lubricity to contact lenses even while they are being worn.

[0070] (Improvement of hydrophilicity of contact lens surfaces) The surface hydrophilicity of the contact lenses treated with the contact lens solutions of Examples 1-15 was found to be excellent or the best at the beginning and during wear. On the other hand, no improvement in the surface hydrophilicity of the contact lens treated with the contact lens solution of Comparative Example 1-5 could be confirmed. As a result, the contact lens solutions of Examples 1-15 can impart excellent (durable) surface hydrophilicity to contact lenses even while they are being worn.

[0071] (Improved ability to inhibit lipid adhesion to contact lenses) The lipid adhesion inhibitory ability of the contact lenses treated with the contact lens solutions of Examples 1-15 was evaluated as "excellent" or "excellent." On the other hand, the ability to inhibit lipid adhesion could not be confirmed for the contact lenses treated with the contact lens solutions of Comparative Examples 1-5. As a result, the contact lens solutions of Examples 1-15 can impart the ability to inhibit lipid adhesion to contact lenses.

[0072] As described above, the contact lens solution of the present disclosure can impart durable surface hydrophilicity, durable lubricity, and lipid adhesion inhibitory properties to contact lenses by a simple treatment (e.g., immersing the contact lenses in the solution), thereby providing contact lens wearers with a comfortable wearing experience. Furthermore, this comfortable wearing experience can be maintained for a long period of time. [Industrial Applicability]

[0073] A contact lens solution can be provided that imparts surface hydrophilicity, lubricity, and lipid adhesion inhibitory properties to contact lenses.

Claims

1. 0.001 to 1.0 w / v% of a copolymer (P) containing structural units represented by formulas (1a) to (1c), wherein the ratio of the numbers of the structural units na:nb:nc is 100:10 to 400:2 to 50 and the weight average molecular weight is 5,000 to 2,000,000; 0.002 to 2.0 wt % of a copolymer (Q) which is a polyoxyethylene-polyoxypropylene block copolymer, the number of moles of ethylene oxide (EO) added being 120 to 200, the number of moles of propylene oxide (PO) added being 10 to 70, and the EO content being 60 to 90 wt %, and a buffering agent; wherein the copolymer contains only the copolymer (P) and the copolymer (Q), Soft contact lens solution. 【Chemistry 1】 【Chemistry 2】 【Transformation 3】 (In the formula, R １ , R ２ and R ５ R each independently represents a hydrogen atom or a methyl group. ３ and R ４ R each independently represent a hydrogen atom, a methyl group, an ethyl group, or combine with each other to form a morpholino group. ６ represents a monovalent hydrocarbon group having 12 to 24 carbon atoms.

2. 2. The soft contact lens solution of claim 1, wherein the buffer is a phosphate buffer.

3. The soft contact lens solution according to claim 1 or 2, wherein the structural unit represented by formula (1a) is a structural unit based on 2-(methacryloyloxy)ethyl 2-(trimethylammonio)ethyl phosphate, the structural unit represented by formula (1b) is a structural unit based on N,N-dimethylacrylamide, and the structural unit represented by formula (1c) is a structural unit based on stearyl methacrylate.

4. The soft contact lens solution according to claim 1 or 2, wherein the structural unit represented by formula (1a) is a structural unit based on 2-(methacryloyloxy)ethyl 2-(trimethylammonio)ethyl phosphate, the structural unit represented by formula (1b) is a structural unit based on N,N-dimethylacrylamide, and the structural unit represented by formula (1c) is a structural unit based on lauryl methacrylate.

5. 2. The soft contact lens solution according to claim 1, which does not contain a cooling agent.

6. 4. The soft contact lens solution according to claim 3, wherein the number of moles of ethylene oxide (EO) added is 160, the number of moles of propylene oxide (PO) added is 30, and the EO content is 80 wt %.

7. 5. The soft contact lens solution according to claim 4, wherein the number of moles of ethylene oxide (EO) added is 160, the number of moles of propylene oxide (PO) added is 30, and the EO content is 80 wt %.

8. A solution for soft contact lenses as described in claim 1, which does not contain polyhexamethylene biguanide or its salts.

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