Treatment liquid for contact lenses

Abstract

The present invention provides a treatment liquid for contact lenses, with which it is possible to achieve both improvement of hydrophilicity of a contact lens surface and sustainability of hydrophilicity improvement effect. The treatment liquid for contact lenses contains a copolymer (P) that has constituent units derived from a monomer (a) represented by formula (1a), a monomer (b) represented by formula (1b) or (2b), and a monomer (c) represented by formula (1c). (R1 represents a hydrogen atom or a methyl group, X represents O or NR2, and R2 represents H or an alkyl group having 1 to 4 carbon atoms.) (R3 represents a hydrogen atom or a methyl group, Y1 represents O or NR4, and R4 represents H or an alkyl group having 1 to 4 carbon atoms.) (R5 represents a hydrogen atom or a methyl group, Y2 represents O or NR6, and R6 represents H or an alkyl group having 1 to 4 carbon atoms.) (R7 represents a hydrogen atom or a methyl group, R8 represents an alkyl group having 1 to 10 carbon atoms, Z represents O or NR9, and R9 represents H or an alkyl group having 1 to 4 carbon atoms.)

Description

Contact lens treatment solution

[0001] This invention relates to a processing solution for contact lenses.

[0002] In recent years, the demand for contact lenses has increased due to the rise in the myopic population accompanying the widespread use of electronic devices such as smartphones. However, many people discontinue wearing contact lenses due to discomfort, and research on improving wearing comfort is still insufficient.

[0003] Poor wearing comfort is said to be caused by increased friction due to poor wettability and dirt on the lenses, which can lead not only to discomfort but also to conjunctivitis and infections.

[0004] To address the above issues, methods for hydrophilizing the surface of contact lenses have been developed. Patent Document 1 discloses a technique for applying plasma treatment to contact lenses. Patent Document 2 discloses a technique for improving the hydrophilicity of a silicone hydrogel lens by having a hydrogel layer with a high water content on its surface. However, Patent Documents 1 and 2 require specialized manufacturing equipment to treat the contact lens itself, which presents cost challenges.

[0005] On the other hand, Patent Document 3 discloses a method for incorporating hydrophilic polymer compounds such as hyaluronic acid into contact lens packing solution. Patent Document 4 discloses a technology that improves wearing comfort by adding a copolymer of a phosphorylcholine group-containing monomer and butyl methacrylate to a soft contact lens processing solution.

[0006] International Publication No. 2010 / 092686, International Publication No. 2012 / 016098, International Publication No. 2013 / 031020, U.S. Patent Application No. 2009 / 0100801

[0007] Although the techniques using the contact lens treatment solutions described in Patent Documents 3 and 4 are excellent in terms of wearing comfort, the hydrophilic polymer compounds and copolymers used in these documents have insufficient adsorptivity to the contact lens and are washed away by tears, so the improvement in wearing comfort was only temporary. In order to maintain a comfortable wearing feeling over a long period of time, it was necessary to enhance the adsorptivity to the contact lens and impart durability to withstand washing by tears.

[0008] The present invention has been made in view of the problems of the above prior art, and an object thereof is to provide a contact lens treatment solution capable of achieving both improvement in hydrophilicity of the contact lens surface and persistence of the hydrophilicity improvement effect.

[0009] As a result of intensive studies, the inventors of the present invention have found that by dissolving a copolymer obtained by copolymerizing at least three types of monomers in a solvent at a specific concentration, an excellent contact lens preparation can be obtained and the above object can be achieved, and the present invention has been completed.

[0010] That is, the present invention consists of the following [1] to [6]. [1] A contact lens treatment solution containing a copolymer (P) composed of a structural unit derived from a monomer (a) represented by the following formula (1a), a structural unit derived from a monomer (b) represented by any one of the following formulas (1b) and (2b), and a structural unit derived from a monomer (c) represented by the following formula (1c). (In formula (1a), R １ is a hydrogen atom or a methyl group, and X is O or NR ２ , where R ２ is H or an alkyl group having 1 to 4 carbon atoms.) (In formula (1b), R ３ is a hydrogen atom or a methyl group, and Y1 is O or NR ４ , where R ４ is H or an alkyl group having 1 to 4 carbon atoms.) (In formula (2b), R ５ is a hydrogen atom or a methyl group, and Y2 is O or NR ６ , where R ６ is H or an alkyl group having 1 to 4 carbon atoms.) (In formula (1c), R ７ R is a hydrogen atom or a methyl group, ８ is an alkyl group having 1 to 10 carbon atoms, which may have a linear or branched structure, and Z is O or NR ９ Here, R ９ (wherein is H or an alkyl group having 1 to 4 carbon atoms.) [2] The contact lens treatment solution according to [1], wherein when the molar ratios of the constituent units derived from monomer (a), monomer (b), and monomer (c) in the copolymer (P) are na, nb, and nc, respectively, na = 40 to 80 mol%, nb = 10 to 40 mol%, and nc = 5 to 25 mol%. [3] The contact lens treatment solution according to [1] or [2], wherein the weight-average molecular weight of the copolymer (P) is 10,000 to 1,000,000. [4] The contact lens treatment solution according to any one of [1] to [3], wherein the monomer (a) is 2-(methacryloyloxy)ethyl 2-(trimethylammonio)ethyl phosphate and the monomer (b) is 2,3-dihydroxypropyl methacrylate or 2-[{(2,3-dihydroxypropoxy)carbonyl}amino]ethyl methacrylate. [5] The contact lens treatment solution according to any one of [1] to [4], wherein the monomer (c) is n-butyl methacrylate. [6] The contact lens treatment solution according to any one of [1] to [5], comprising 0.001 w / v% or more and 5.0 w / v% or less of the copolymer (P).

[0011] The present invention provides a treatment solution for contact lenses that can achieve both improved hydrophilicity of the contact lens surface and sustained hydrophilicity improvement.

[0012] The present invention will be described in more detail below.

[0013] In this specification, when preferred numerical ranges (e.g., ranges for concentration or weight-average molecular weight) are described in steps, each lower and upper limit can be combined independently. For example, in the description "preferably 10 to 100, more preferably 20 to 90," the "preferred lower limit: 10" and the "more preferred upper limit: 90" can be combined to make "10 or more and 90 or less." In other words, it can be "10 to 90."

[0014] In this specification, "(meth)acrylic" means acrylic or methacrylic (methacrylic), "(meth)acryloyl" means acryloyl or methacryloyl (methacryloyl), "(meth)acrylate" means acrylate or methacrylate (methacrylate), and "(meth)acrylamide" means acrylamide or methacrylamide (methacrylamide).

[0015] Specific product forms of contact lens processing solutions include the following: Specifically, contact lens packing solution (contact lens shipping solution), contact lens storage solution, contact lens cleaning solution, contact lens cleaning and storage solution, contact lens care products, contact lens disinfectants, contact lens insertion solutions, and processing solutions for contact lens surface treatment.

[0016] In this specification, "contact lens packing solution" refers to an aqueous solution that is sealed in a packaging container such as a blister package along with the contact lenses when they are distributed. Generally, contact lenses are used in a swollen state with the aqueous solution, so the lenses are sealed in a packaging container with the aqueous solution (contact lens packing solution) swollen at the time of shipment so that they can be used immediately.

[0017] [Copolymer (P)] The copolymer (P) contained in the treatment liquid for contact lenses is obtained by polymerizing a monomer (a) represented by the following formula (1a), a monomer (b) represented by either of the following formulas (1b) and (2b), and a monomer (c) represented by the following formula (1c). Therefore, the copolymer (P) includes a structural unit derived from the monomer (a), a structural unit derived from the monomer (b), and a structural unit derived from the monomer (c).

[0018]

[0019] (In formula (1a), R １ is a hydrogen atom or a methyl group, and X is O or NR ２ , where R ２ is H or an alkyl group having 1 to 4 carbon atoms.)

[0020]

[0021] (In formula (1b), R ３ is a hydrogen atom or a methyl group, and Y1 is O or NR ４ , where R ４ is H or an alkyl group having 1 to 4 carbon atoms.)

[0022]

[0023] (In formula (2b), R ５ is a hydrogen atom or a methyl group, and Y2 is O or NR ６ , where R ６ is H or an alkyl group having 1 to 4 carbon atoms.)<​​​​​​​​​​​​​​​Copolymer (P) is a hydrophilic polymer with high affinity for the contact lens surface. By using such copolymer (P) in a contact lens treatment solution, high hydrophilicity can be imparted to the contact lens surface and maintained. For this reason, a contact lens treatment solution containing copolymer (P) is particularly useful as a packing solution for contact lenses.

[0027] [Monomer (a)] The copolymer (P) has constituent units derived from the phosphorylcholine group-containing monomer (a) represented by formula (1a). Monomer (a) can enhance the hydrophilicity of copolymer (P) and improve the hydrophilic effect of copolymer (P) on the contact lens surface. Note that monomer (a) is not limited to one type, and one or more types can be used.

[0028]

[0029] (In formula (1a), R １ is a hydrogen atom or a methyl group, and X is O or NR ２ Here, R ２ (This is either H or an alkyl group having 1 to 4 carbon atoms.)

[0030] Examples of monomers containing a phosphorylcholine group include 2-(meth)acryloyloxy)ethyl-2-(trimethylammonio)ethyl phosphate and 2-(meth)acrylamide)ethyl-2-(trimethylammonio)ethyl phosphate, and more preferably 2-(methacryloyloxy)ethyl 2-(trimethylammonio)ethyl phosphate (also known as 2-methacryloyloxyethyl phosphorylcholine).

[0031] The monomer represented by formula (1a) can be produced by known methods, for example, by reacting a hydroxyl group-containing polymerizable monomer with 2-bromoethylphosphoryl dichloride in the presence of a tertiary base, and then reacting the resulting compound with a tertiary amine. Alternatively, a method may be used in which a cyclic compound is obtained by reacting a hydroxyl group-containing polymerizable monomer with a cyclic phosphorus compound, and then a ring-opening reaction is carried out with a tertiary amine.

[0032] The content of monomer (a) in copolymer (P) is not particularly limited, but can be, for example, 10 to 80 mol%, preferably 40 to 80 mol%, more preferably 50 to 70 mol%, and even more preferably 55 to 65 mol%. When the content is 40 mol% or more, the hydrophilicity of copolymer (P) is sufficiently increased, and the effect of imparting hydrophilicity to contact lenses is further enhanced. When the content is 80 mol% or less, the content of monomers (b) and (c) can be increased to improve the adsorption of copolymer (P) to the contact lens surface, making it easier to sustain the hydrophilic effect.

[0033] Furthermore, multiple types of monomers (a) can be used in any ratio. In that case, the above content refers to the total number of moles of all monomers (a) combined.

[0034] [Monomer (b)] The copolymer (P) has constituent units derived from a polyhydric hydroxyl group-containing monomer (b) represented by the following formula (1b) or (2b). By coexisting monomer (b) with monomer (c), the adsorption of copolymer (P) to the contact lens surface can be improved and the hydrophilic effect can be sustained. Note that monomer (b) is not limited to one type, and one or more types can be used.

[0035]

[0036] (In formula (1b), R ３ is a hydrogen atom or a methyl group, and Y1 is O or NR ４ Here, R ４ (This is either H or an alkyl group having 1 to 4 carbon atoms.)

[0037]

[0038] (In formula (2b), R ５ is a hydrogen atom or a methyl group, and Y2 is O or NR ６ Here, R ６ (This is either H or an alkyl group having 1 to 4 carbon atoms.)

[0039] Examples of monomers represented by formula (1b) include 2,3-hydroxypropyl (meth)acrylate (also known as glycerol (meth)acrylate), and more preferably 2,3-dihydroxypropyl methacrylate (glycerol methacrylate).

[0040] Examples of monomers represented by formula (2b) include 2-[{(2,3-dihydroxypropoxy)carbonyl}amino]ethyl (meth)acrylate, and more preferably 2-[{(2,3-dihydroxypropoxy)carbonyl}amino]ethyl methacrylate.

[0041] The monomer (b) content in the copolymer (P) is not particularly limited, but can be, for example, 10 to 80 mol%, preferably 10 to 40 mol%, more preferably 15 to 30 mol%, and even more preferably 15 to 25 mol%. When the content is 10 mol% or more, the adsorption of the copolymer (P) to the contact lens surface is sufficiently increased, making it easier to sustain the hydrophilic effect. When the content is 40 mol% or less, the monomer (a) content is increased, thereby increasing the hydrophilicity of the copolymer (P) and further enhancing the hydrophilic effect on the contact lens.

[0042] Furthermore, multiple types of monomers (b) can be used in any ratio. In that case, the above content refers to the total number of moles of all monomers (b) combined.

[0043] The content of monomers (a) and (b) is not limited to the examples described above. For example, in another aspect of the present invention, the content of monomer (a) in copolymer (P) is preferably 10 to 40 mol%, more preferably 15 to 40 mol%, and even more preferably 20 to 35 mol%. When the content is 10 mol% or more, the hydrophilicity of copolymer (P) increases, and the effect of imparting hydrophilicity to contact lenses is further enhanced. When the content is 40 mol% or less, the content of monomers (b) and (c) can be increased to improve the adsorption of copolymer (P) to the contact lens surface, making it easier to sustain the hydrophilic effect.

[0044] In this embodiment, the content of monomer (b) in the copolymer (P) is preferably 40 to 80 mol%, more preferably 50 to 70 mol%, and 55 to 65 mol%. If the content is greater than 40 mol%, the adsorption of copolymer (P) to contact lenses can be further enhanced, and the hydrophilic effect can be made to last longer. If the content is 80 mol% or less, the content of monomer (a) can be increased to enhance the hydrophilicity of copolymer (P), and the hydrophilic effect on contact lenses can be enhanced.

[0045] [Monomer (c)] The copolymer (P) has constituent units derived from the hydrophobic monomer (c) represented by the following formula (1c). By coexisting monomer (c) with monomer (b), the adsorption of copolymer (P) to the contact lens surface can be improved and the hydrophilic effect can be sustained. Note that the hydrophobic monomer (c) is not limited to one type, and one or more types can be used.

[0046]

[0047] (In formula (1c), R ７ R is a hydrogen atom or a methyl group, ８ is an alkyl group having 1 to 10 carbon atoms, which may have a linear or branched structure, and Z is O or NR ９ Here, R ９ (This is either H or an alkyl group having 1 to 4 carbon atoms.)

[0048] A preferred example of monomer (c) is R ８ n-butyl (meth)acrylate, which is a linear alkyl group with 4 carbon atoms, R ８ n-hexyl (meth)acrylate, which is a linear alkyl group with 6 carbon atoms, R ８ tert-butyl (meth)acrylate, R is an alkyl group having four carbon atoms and a branched structure. ８ Examples include 2-ethylhexyl (meth)acrylate, which is an alkyl group having eight carbon atoms and a branched structure. More preferably is n-butyl (meth)acrylate, and even more preferably is n-butyl methacrylate.

[0049] The monomer (c) content in the copolymer (P) is not particularly limited, but is preferably 5 to 25 mol%, more preferably 10 to 25 mol%, and even more preferably 10 to 20 mol%. When the content is 5 mol% or more, the adsorption of the copolymer (P) to the contact lens surface is sufficiently increased, making it easier to sustain the hydrophilic effect. When the content is 25 mol% or less, the content of monomer (a) is increased to enhance the hydrophilicity of the copolymer (P), further enhancing the hydrophilic effect on the contact lens. Also, when the content is 25 mol% or less, the solubility in water does not decrease easily, making it easier to prepare the treatment solution for contact lenses.

[0050] Furthermore, multiple types of monomers (c) can be used in any ratio. In that case, the above content refers to the total number of moles of all monomers (c) combined.

[0051] [Other monomers] Copolymer (P) may contain monomer (d) other than monomer (a), monomer (b), and monomer (c).

[0052] Monomer (d) can be arbitrarily selected from monomer (a), monomer (b), and monomer (d) copolymerizable with monomer (c).

[0053] Examples of such monomers (d) include styrene sulfonic acid, (meth)acryloyloxyphosphonic acid, 2-hydroxy-3-(meth)acryloyloxypropyltrimethylammonium chloride, polyethylene glycol (meth)acrylate, aminoethyl (meth)acrylate, N,N-dimethylaminoethyl (meth)acrylate, N-acryloylmorpholine, (meth)cyclohexyl acrylate, (meth)stearyl acrylate, styrene, α-methylstyrene, vinyltoluene, indene, vinylnaphthalene, vinylaniline, ethylene, propylene, butadiene, isobutylene, alkenes such as octene, acrylonitrile, methacrylonitrile, polypropylene glycol (meth)acrylate, and others. One or more of these can be used. The ratio of monomer (d) to all monomers used when preparing copolymer (P) is preferably 30 mol% or less, and more preferably 15 mol% or less. The lower limit of the ratio of monomer (d) is not particularly limited, but it can be 0 mol% or more. Within the above range, the effects of monomer (a), monomer (b), and monomer (c) can be fully exerted, and if necessary, the properties of monomer (d) can also be imparted to copolymer (P).

[0054] [Weight-average molecular weight of copolymer (P)] The weight-average molecular weight of copolymer (P) is not particularly limited, but is preferably 10,000 to 1,000,000, more preferably 20,000 to 500,000, and even more preferably 40,000 to 100,000. By setting the weight-average molecular weight of copolymer (P) to 10,000 or more, the hydrophilic effect on contact lenses can be enhanced, and the production of copolymer (P) can be made easier. By setting the weight-average molecular weight of copolymer (P) to 1,000,000 or less, interaction with the contact lens surface can be facilitated, and the duration of the hydrophilic effect can be increased. In addition, the handling of copolymer (P) can be made easier.

[0055] The weight-average molecular weight of the copolymer (P) is determined by GPC (gel filtration chromatography) measurement, expressed in terms of polyethylene glycol / oxide.

[0056] [Polymerization form of copolymer (P)] Copolymer (P) is usually a random copolymer, but it may also be an alternating copolymer or a block copolymer in which each monomer is arranged regularly, and may have a graft structure in part.

[0057] [Method for producing copolymer (P)] Copolymer (P) can be produced by copolymerizing monomer (a) represented by formula (1a), monomer (b) represented by either formula (1b) or (2b), and monomer (c) represented by formula (1c).

[0058] The above polymerization reaction can be carried out by radical polymerization in the presence of a radical initiator, substituted with an inert gas such as nitrogen, carbon dioxide, argon, or helium, or in an atmosphere, using known methods such as bulk polymerization, suspension polymerization, emulsion polymerization, or solution polymerization. Solution polymerization is preferred from the viewpoint of purification. The copolymer can be purified by general purification methods such as reprecipitation, dialysis, or ultrafiltration.

[0059] Examples of radical polymerization initiators include azo radical polymerization initiators, organic peroxides, and persulfur oxides.

[0060] Examples of azo radical polymerization initiators include 2,2'-azobis(2-methylpropionamidine) dihydrochloride (V-50), 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).

[0061] Examples of organic peroxides include t-butylperoxyneodecanoate (Perbutyl® ND), benzoyl peroxide, diisopropyl peroxydicarbonate, t-butylperoxy-2-ethylhexanoate, t-butylperoxypivalate, t-butylperoxydiisobutyrate, lauroyl peroxide, and succinate peroxide (succinyl peroxide).

[0062] Examples of persulfur oxides include ammonium persulfate, potassium persulfate, and sodium persulfate.

[0063] As a radical polymerization initiator, it is preferable to use an organic peroxide, and more preferably to use t-butylperoxyneodecanoate (Perbutyl® ND).

[0064] These radical polymerization initiators can be used individually or in combination of two or more. The amount of 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 of the copolymer (P).

[0065] Polymerization reactions can be carried out in the presence of a solvent, which can be any solvent that dissolves the monomer composition without reacting with it. Examples of such solvents include alcoholic solvents such as water, methanol, ethanol, n-propanol, and isopropanol; ketoneic solvents such as acetone, methyl ethyl ketone, and diethyl ketone; esteric solvents such as ethyl acetate; linear or cyclic etheric solvents such as ethyl cellosolve, tetrahydrofuran, and N-methylpyrrolidone; and nitrogen-containing solvents such as acetonitrile and nitromethane. Preferably, water, alcohol, or a mixture thereof is used, and more preferably, a mixture of water and ethanol is used.

[0066] [Contact Lens Treatment Solution] The concentration of copolymer (P) in the contact lens treatment solution is not particularly limited, but is preferably 0.001 w / v% or more, more preferably 0.01 w / v% or more, and even more preferably 0.1 w / v% or more. Furthermore, the concentration of copolymer (P) is 5.0 w / v% or less, preferably 2.0 w / v% or less, and more preferably 0.7 w / v% or less. By setting the concentration of copolymer (P) to 0.001 w / v% or more, a sufficient hydrophilic effect can be obtained, and from the viewpoint of the manufacturability of the contact lens treatment solution, it is desirable to set the concentration of copolymer (P) to 5.0 w / v% or less.

[0067] In this specification, "w / v%" refers to the mass of a component in grams (g) in 100 mL of solution. For example, "the composition contains 1.0 w / v% copolymer (P)" means that 100 mL of solution contains 1.0 g of copolymer (P).

[0068] As solvents used in contact lens processing solutions, water, ethanol, n-propanol, isopropanol, glycerol, propylene glycol, and other alcohols or mixtures thereof can be used. Preferably, water or a mixture of water and alcohol is used, and more preferably, water.

[0069] The water used in contact lens processing solutions can typically be the same water 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.

[0070] Contact lens treatment solutions can contain buffering agents. By including buffering agents in the contact lens treatment solution, the pH and osmotic pressure can be adjusted, further improving the user experience.

[0071] From the viewpoint of obtaining the aforementioned effects more fully, it is desirable to use one or more buffers selected from phosphate buffers and borate buffers. In this specification, a phosphate buffer is a buffer consisting of disodium hydrogen phosphate, sodium dihydrogen phosphate, anhydrous sodium dihydrogen phosphate, potassium dihydrogen phosphate, dipotassium hydrogen phosphate, hydrochloric acid, sodium hydroxide, potassium hydroxide, etc., and a borate buffer is a buffer consisting of boric acid, borax, hydrochloric acid, sodium hydroxide, potassium hydroxide, etc.

[0072] The concentration of the buffer in the contact lens processing solution is preferably 0.0001 w / v% to 15 w / v%, more preferably 0.001 w / v% to 10 w / v%, and even more preferably 0.01 w / v% to 5.0 w / v%.

[0073] In particular, when one or more buffers selected from phosphate buffer and borate buffer are used, their concentration is preferably 0.001 w / v% to 10 w / v%, more preferably 0.01 w / v% to 5.0 w / v%, and even more preferably 0.1 w / v% to 5.0 w / v%, as the total of the components of the phosphate buffer and borate buffer.

[0074] The contact lens treatment solution may further contain, as needed, ingredients commonly used in ophthalmic formulations, such as decongestants, anti-inflammatory and astringent ingredients, vitamins, cooling agents, isotonic agents, pH adjusters, antioxidants, stabilizers, preservatives, mucin secretion promoters, and thickeners.

[0075] Examples of decongestant ingredients include epinephrine or its salts, ephedrine hydrochloride, tetrahydrozoline hydrochloride, naphazoline or its salts, phenylephrine, and methyl ephedrine hydrochloride.

[0076] Examples of anti-inflammatory and astringent ingredients include epsilon-aminocaproic acid, allantoin, berberine or its salts, sodium azulene sulfonate, glycyrrhizic acid or its salts, zinc lactate, zinc sulfate, and lysozyme chloride.

[0077] Examples of vitamins include flavin adenine dinucleotide sodium, cyanocobalamin, retinyl acetate, retinyl palmitate, pyridoxine hydrochloride, panthenol, sodium pantothenate, and calcium pantothenate.

[0078] Examples of cooling agents include menthol and camphor.

[0079] Examples of isotonic agents include sodium chloride, potassium chloride, magnesium chloride, calcium chloride, aspartic acid or its salts, and aminoethylsulfonic acid.

[0080] Examples of pH adjusting agents include citric acid, sulfuric acid, acetic acid, trishydroxymethylaminomethane, monoethanolamine, sodium bicarbonate, and sodium citrate.

[0081] Examples of antioxidants include tocopherol acetate, dibutylhydroxytoluene, and sodium bisulfite.

[0082] Examples of stabilizers include sodium edetate, glycine, and taurine.

[0083] Examples of preservatives include benzalkonium chloride, chlorhexidine gluconate, potassium sorbate, methylparaben, ethylparaben, propylparaben, isopropylparaben, butylparaben, isobutylparaben, polyhexanide hydrochloride, sulfamexazole or its salts, sulfisoxazole, and sulfisomidine sodium.

[0084] Examples of mucin secretion promoters include diquafosol sodium and rebamipide.

[0085] Examples of thickening agents include poly(meth)acrylic acid, (meth)acrylic acid-acrylic(meth)acrylate copolymer, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, carboxymethylcellulose, polyvinylpyrrolidone, polyvinyl alcohol, and polyethylene glycol.

[0086] From the viewpoint of minimizing eye irritation, the pH of the contact lens processing solution is preferably 3.0 to 8.0, more preferably 3.8 to 7.8, and even more preferably 4.0 to 7.6.

[0087] From the viewpoint of minimizing eye irritation, the osmotic pressure of the contact lens treatment solution is preferably 200 mOsm to 400 mOsm, more preferably 225 mOsm to 375 mOsm, and even more preferably 230 mOsm to 340 mOsm. 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.

[0088] In this specification, the osmotic pressure of the contact lens treatment solution refers to the value measured according to the 2.47 Osmotic Pressure Measurement Method (Osmolality Measurement Method) of the 18th Revised 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% by mass physiological saline solution (286 mOsm).

[0089] [Method for Manufacturing Contact Lens Treatment Solution] The contact lens treatment solution can be manufactured using a general method for manufacturing contact lens treatment solutions. For example, it can be manufactured by mixing a copolymer (P), a solvent and other components as needed, and stirring. The resulting contact lens treatment solution may be subjected to sterile filtration or other operations as needed.

[0090] [Target Lenses for Contact Lens Treatment Solution] The contact lenses targeted by the contact lens treatment solution are not particularly limited, but examples include nonionic low water content lenses (Group I), nonionic high water content lenses (Group II), ionic low water content lenses (Group III), ionic high water content lenses (Group IV), silicone hydrogel lenses, etc., and lenses having amide bonds that act as hydrogen bond acceptors are preferred. Examples of such amide bonds include N,N-dimethylacrylamide and its polymers, acrylamide and its polymers, N-vinylpyrrolidone and its polymers, and lenses having N-vinylpyrrolidone and its polymers are more preferred.

[0091] The present invention will be described in more detail below based on examples and comparative examples, but the present invention is not limited thereto.

[0092] <Copolymer (P)> Copolymers P1 to P9 were used as examples. The molar ratios of each constituent monomer in copolymers P1 to P9 are shown in Table 1. In Table 1, MPC refers to 2-(methacryloyloxy)ethyl 2-(trimethylammonio)ethyl phosphate, GLM refers to glycerol methacrylate, and BMA refers to n-butyl methacrylate.

[0093] <Comparative Copolymer (Q)> As comparative examples, comparative copolymers Q1 and Q2, whose molar ratios of constituent monomers are shown in Table 1, were used.

[0094] <Measurement of Weight-Average Molecular Weight> Copolymers P1-P9 and comparative copolymers Q1 and Q2 were dissolved in deionized water to a concentration of 0.1 wt%, and their weight-average molecular weight was measured by gel permeation chromatography (GPC). Other measurement conditions were as follows. The measurement results are shown in Table 1. Column: SB-802.5HQ + SB-806M HQ Mobile phase: 20 mM phosphate buffer (pH 7.4) Standard substance: Polyethylene glycol / oxide Measuring instrument: HLC-8420GPC (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: 100 μL Column oven: 45°C Measurement time: 60 minutes

[0095]

[0096] <Test contact lenses used for evaluation> Lens A: 1-Day Acuvue Oasys (manufactured by Johnson & Johnson K.K.) Lens B: Aqualox (manufactured by Bausch + Lomb K.K.) Lens C: 1-Day Acuvue Moist (manufactured by Johnson & Johnson K.K.) Lens D: 1-Day Fine UV Plus (manufactured by Seed Co., Ltd.)

[0097] <Preparation of physiological saline solution> Physiological saline solution was prepared based on the literature (ISO 18369-3:2006, Optical Optics-Contact Lenses Part 3: Measurement Methods).

[0098] 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.

[0099] <Preparation of Contact Lens Treatment Solution> Using the physiological saline solution and copolymer prepared above, the contact lens treatment solutions for Examples 1 to 9 and Comparative Examples 1 to 2 were prepared by blending them as shown in Table 2.

[0100] <Evaluation of Hydrophilicity-Imparting Effect and Durability of Contact Lenses> In the examples and comparative examples, the hydrophilicity-imparting effect and durability of the contact lens treatment solution were evaluated according to the following procedure. The results are shown in Table 2. A lower contact angle indicates higher hydrophilicity, and a larger difference in contact angle with the blank lens, i.e., a higher contact angle score, indicates a higher hydrophilicity-imparting effect. Durability was evaluated by washing with physiological saline solution as a substitute for tears to assess durability against washing with tears. The evaluation before washing simulates the start of contact lens wear, and the evaluation after washing simulates the state after wearing the contact lens all day.

[0101] (1) The test contact lenses removed from the blister pack were immersed in physiological saline solution and shaken for 6 hours. (2) The test contact lenses were sealed in glass vials containing 5 mL of physiological saline solution and glass vials containing 5 mL of the contact lens treatment solution listed in Table 2. (3) The lenses were sterilized at 121°C for 20 minutes. (4) The test contact lenses sterilized in physiological saline solution were removed from the glass vials, excess moisture was wiped off with a water-moistened Bencot (manufactured by Asahi Kasei Corporation), and the contact angle was measured using a DropMaster 500 contact angle meter (manufactured by Kyowa Interface Science Co., Ltd.) by the liquid application method. Measurements were performed with n=3, and the average value was taken as the contact angle of the blank lens. (5) The test contact lenses treated in each contact lens treatment solution listed in Table 2 were removed from the glass vials, and the contact angle was measured in the same manner as above. Measurements were performed with n=3, and the average value was taken as the contact angle before washing. (6) The pre-cleaning contact angle score was evaluated based on the difference from the contact angle of the blank lens, according to the following criteria.

[0102] Contact Angle Score Criteria Before Cleaning Difference from the contact angle of the blank lens: 50° or more: Score "3" 20° or more but less than 50°: Score "2" 10° or more but less than 20°: Score "1" Less than 10°: Score "0"

[0103] (7) Durability evaluation was performed using the lenses from (3). The test contact lenses were removed from the glass vials and immersed in 2 mL of another physiological saline solution. After shaking and washing at 37°C, 100 rpm for 30 minutes, the contact angle was measured. Measurements were taken with n=3, and the average value was taken as the post-wash contact angle. (8) The post-wash contact angle score was evaluated based on the difference from the contact angle of the blank lens according to the following criteria.

[0104] Contact Angle Score after Cleaning: Difference from the contact angle of the standard blank lens: 25° or more: Score "3" 15° or more and less than 25°: Score "2" 5° or more and less than 15°: Score "1" Less than 5°: Score "0"

[0105]

[0106] <Evaluation> From the results in Table 2, it was found that the contact lens treatment solution using copolymers P1 to P9 significantly reduced the contact angle of the contact lens and improved its hydrophilicity. Furthermore, since the contact angle remained low after washing, it was found that the solution had excellent washing durability and the hydrophilic effect was sustained.

[0107] The contact lens treatment solutions using Q1 and Q2 slightly reduced the contact angle of the contact lenses, but not sufficiently, and the high contact angle after washing indicated insufficient adsorption to the lenses.

[0108] This application claims priority to Japanese Patent Application No. 2024-179826, filed on 15 October 2024. The matters set forth in the original specification and claims of said application are incorporated herein by reference.

[0109] The contact lens treatment solution of the present invention can impart hydrophilicity to contact lenses and has excellent adsorption properties to contact lenses, thus allowing the hydrophilic effect to be sustained.

Claims

1. A treatment liquid for contact lenses, comprising a copolymer (P) having a structural unit derived from a monomer (a) represented by the following formula (1a), a structural unit derived from a monomer (b) represented by any one of the following formulas (1b) and (2b), and a structural unit derived from a monomer (c) represented by the following formula (1c). (In formula (1a), R １ is a hydrogen atom or a methyl group, and X is O or NR ２ , where R ２ is H or an alkyl group having 1 to 4 carbon atoms.) (In formula (1b), R ３ is a hydrogen atom or a methyl group, and Y1 is O or NR ４ , where R ４ is H or an alkyl group having 1 to 4 carbon atoms.) (In formula (2b), R ５ is a hydrogen atom or a methyl group, and Y2 is O or NR ６ , where R ６ is H or an alkyl group having 1 to 4 carbon atoms.) (In formula (1c), R ７ is a hydrogen atom or a methyl group, R ８ is an alkyl group having 1 to 10 carbon atoms, which may be a linear structure or a branched structure, and Z is O or NR ９ , where R ９ is H or an alkyl group having 1 to 4 carbon atoms.) 2. The contact lens treatment solution according to claim 1, wherein when the content of constituent units derived from monomer (a), constituent units derived from monomer (b), and constituent units derived from monomer (c) in the copolymer (P) is na, nb, and nc, respectively, na = 40 to 80 mol%, nb = 10 to 40 mol%, and nc = 5 to 25 mol%.

3. The contact lens treatment solution according to claim 1, wherein the weight-average molecular weight of the copolymer (P) is 10,000 to 1,000,000.

4. The contact lens treatment solution according to claim 1, wherein monomer (a) is 2-(methacryloyloxy)ethyl 2-(trimethylammonio)ethyl phosphate, and monomer (b) is 2,3-dihydroxypropyl methacrylate or 2-[{(2,3-dihydroxypropoxy)carbonyl}amino]ethyl methacrylate.

5. The contact lens treatment solution according to claim 1, wherein the monomer (c) is n-butyl methacrylate.

6. The contact lens treatment solution according to claim 1, comprising 0.001 w / v% or more and 5.0 w / v% or less of the copolymer (P).

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