Maleic anhydride-based polymer, lens with hydrophilic coating, treatment agent for lens, and composition for lens

Abstract

The present invention provides a maleic anhydride-based polymer, a lens having a hydrophilic coating, a treatment agent for a lens, and a composition for a lens. The maleic anhydride-based polymer includes one or more first repeating units represented by the following Formula I, one or more second repeating units represented by the following Formula II, and one or more third repeating units represented by the following Formula III. Ra in the formula II is H or C1-C3 alkyl, and Rb is H or C1-C3 alkyl or a first repeating unit or a second repeating unit or a third repeating unit. [Formula I] [Formula II] [Formula III]

Description

TECHNICAL FIELD

[0001] The present application relates to a maleic anhydride-based polymer, a lens with a hydrophilic coating, a treating agent for a lens, and a composition for a lens. BACKGROUND

[0002] Maleic anhydride-containing compounds are common materials for improving hydrophilicity, which can be used to form a hydrophilic coating, a contact lens, a treating agent for a contact lens, etc. However, the poor solubility of maleic anhydride can cause suspended particles in the solution, and the maleic anhydride solution appears cloudy, which increases the difficulty of the process, reduces the reactivity of the maleic anhydride-containing compound with other materials, and also causes poor quality of the formed product. SUMMARY

[0003] The present application relates to a maleic anhydride-based polymer and a lens with a hydrophilic coating, which modifies the maleic anhydride-containing compound to improve the solubility, thereby improving the hydrophilicity and stability of the hydrophilic coating to improve the wearing comfort of the user. At the same time, the lens has excellent effect of resisting grease adsorption. The present application relates to a treating agent for a lens and a composition for a lens, which comprises a maleic anhydride-based polymer, thereby improving the hydrophilicity of the lens to improve the wearing comfort of the user.

[0004] According to an embodiment of the present application, a maleic anhydride-based polymer is provided. The maleic anhydride-based polymer comprises one or more first repeating units represented by the following formula I, one or more second repeating units represented by the following formula II, and one or more third repeating units represented by the following formula III. In formula II, R a is H or C1-C3 alkyl, and R b is H or C1-C3 alkyl or the first repeating unit or the second repeating unit or the third repeating unit.

[0005] [Formula I]

[0006]

[0007] [Formula II]

[0008]

[0009] [Formula III]

[0010]

[0011] According to an embodiment of the present application, a lens with a hydrophilic coating is provided. The lens with the hydrophilic coating includes a lens body and a hydrophilic coating. The hydrophilic coating is formed at least partially on an outer surface of the lens body. The hydrophilic coating includes a first polymer. The first polymer includes one or more first repeating units represented by the following Formula I, one or more second repeating units represented by the following Formula II, and one or more fourth repeating units represented by the following Formula IV. R1 in Formula IV is H or a substituent including at least one of a primary amine group, a secondary amine group, and a tertiary amine group. R2 in Formula IV is a substituent including at least one of a primary amine group, a secondary amine group, and a tertiary amine group. R a is H or C1-C3 alkyl, R b is H or C1-C3 alkyl or the first repeating unit or the second repeating unit or the fourth repeating unit.

[0012] [Formula I]

[0013]

[0014] [Formula II]

[0015]

[0016] [Formula IV]

[0017]

[0018] According to an embodiment of the present application, a treating agent for a lens is provided. The treating agent includes a buffer solution and a maleic anhydride-based polymer.

[0019] According to an embodiment of the present application, a composition for a lens is provided. The composition includes a maleic anhydride-based polymer and a polymerizable monomer. BRIEF DESCRIPTION OF DRAWINGS

[0020] In order to make the above objects, features and advantages of the present application more clear and comprehensible, a detailed description of the preferred embodiments will be made with reference to the accompanying drawings, in which:

[0021] Figure 1 is a schematic view showing a lens body according to an embodiment of the present application;

[0022] Figure 2 is a schematic view showing a lens according to an embodiment of the present application; and

[0023] Figure 3 is a schematic view showing a lens according to another embodiment of the present application.

[0024] REFERENCE NUMERALS:

[0025] 10: lens body

[0026] 11: Front surface

[0027] 12: Back surface

[0028] 13: Edge

[0029] 20: Hydrophilic coating

[0030] 20S1: First side

[0031] 20S2: Second side

[0032] 30: Basal layer

[0033] 100, 200: Lenses

[0034] D1: Normal direction

[0035] S: Outer surface Detailed Implementation

[0036] <Polymers Based on Maleic Anhydride and Their Manufacturing Methods>

[0037] The maleic anhydride-based polymer of the present invention comprises z first repeating units represented by Formula I, m second repeating units represented by Formula II, and p third repeating units represented by Formula III. Where z, m, and p are integers greater than or equal to 1 or non-integers. In Formula I, the line segment extending from inside to outside the parentheses represents a bond to another repeating unit or other functional group, which may be a first repeating unit, a second repeating unit, or a third repeating unit. R in Formula II... a It is H or C1-C3 alkyl, R b The repeating unit is H or a C1-C3 alkyl group or another repeating unit, which can be a first repeating unit, a second repeating unit, or a third repeating unit. In Formula III, the line segment extending from inside the brackets to outside the brackets represents a bond to another repeating unit or other functional group, which can be a first repeating unit, a second repeating unit, or a third repeating unit. In maleic anhydride-based polymers, one or more first repeating units, one or more second repeating units, and one or more third repeating units can be randomly bonded to each other.

[0038] [Formula I]

[0039]

[0040] [Formula II]

[0041]

[0042] [Formula III]

[0043]

[0044] In one embodiment, the mole ratio of the second repeating unit to the third repeating unit in the maleic anhydride-based polymer is between 0.5 and 50, for example, between 2 and 30. In one embodiment, the mole ratio of the second repeating unit to the third repeating unit in the maleic anhydride-based polymer can be 2.3, 2.5, 3, 8, or 21.

[0045] In one embodiment, z is between 4 and 50, for example, between 7 and 11. In one embodiment, m is between 10 and 50, for example, between 20 and 45, or between 30 and 40. In one embodiment, p is between 1 and 20, for example, between 5 and 15. The content of the third repeating unit can be between 0.5 wt% (weight percent concentration) and 9 wt%, for example, between 0.8 wt% and 8 wt%, or between 2.5 wt% and 7.4 wt%, based on the total weight of the maleic anhydride-based polymer described above. If the content of the third repeating unit is too low, the maleic anhydride-based polymer is less reactive when used to form a hydrophilic coating. If the content of the third repeating unit is too high, the solubility in water is poor and even precipitation can occur.

[0046] The weight-average molecular weight (Mw) of the maleic anhydride-based polymer can be between 5,000 and 1,500,000, for example, between 5,000 and 1,000,000 or between 5,000 and 500,000. The infrared spectrum of the maleic anhydride-based polymer has at least one absorption peak near 1780 cm -1 and at least one absorption peak near 1728 cm -1 .

[0047] In the maleic anhydride-based polymer, at least one first repeating unit can be bonded to a second repeating unit, and at least one third repeating unit can be bonded to a second repeating unit. In one embodiment, in the maleic anhydride-based polymer, a plurality of first repeating units can be bonded to each other to form a first chain structure, a plurality of second repeating units can be bonded to each other to form a second chain structure, and a plurality of third repeating units can be bonded to each other to form a third chain structure, a first repeating unit at the end of the first chain structure can be bonded to a second repeating unit in the second chain structure, and a third repeating unit at the end of the third chain structure can be bonded to a second repeating unit in the second chain structure. In one embodiment, the maleic anhydride-based polymer can be represented by the following formula A, in which z, m, and p are in the ranges described above.

[0048] [Formula A]

[0049]

[0050] A method of manufacturing a maleic anhydride-based polymer will be described below through an example, but the present application is not limited thereto, and the maleic anhydride-based polymer can also be formed through other manufacturing methods.

[0051] The maleic anhydride-based polymer can be formed by reacting a maleic anhydride-containing compound with polyethylene glycol dimethacrylate (PEGMA). In an embodiment, the method of manufacturing the maleic anhydride-based polymer can include the steps of: placing the maleic anhydride-containing compound, the polyethylene glycol dimethacrylate, and a starter in a solvent to form a raw material solution; stirring the raw material solution under a nitrogen atmosphere to allow the maleic anhydride-containing compound to react with the polyethylene glycol dimethacrylate to form the maleic anhydride-based polymer. The starter can include or be a photostarter or a thermal starter.

[0052] The type and amount of the photostarter and the thermal starter to be added can be selected by those having ordinary knowledge in the art as needed. The solvent can be methanol, ethanol, acetone, dimethyl sulfoxide, dimethylformamide, tetrahydrofuran, N-methyl-2-pyrrolidone, or dimethylacetamide. The maleic anhydride-containing compound can include or be maleic anhydride.

[0053] The method of manufacturing the maleic anhydride-based polymer can further include the steps of heating or irradiating the raw material solution with light, and / or performing reduced pressure concentration, and / or washing the product with a washing solution. The method of manufacturing the maleic anhydride-based polymer can be understood as a modification of the maleic anhydride-containing compound using the polyethylene glycol dimethacrylate. The method of manufacturing the maleic anhydride-based polymer can include a radical polymerization reaction.

[0054] <Applications of the maleic anhydride-based polymer>

[0055] The maleic anhydride-based polymer of the present application can be applied to various products to improve their hydrophilicity, such as a hydrophilic coating, a lens having hydrophilicity, and a treatment agent having hydrophilicity. In an embodiment, the maleic anhydride-based polymer can be used to form a hydrophilic coating in a lens. The following will describe an application of the maleic anhydride-based polymer in a lens. Figure 1 With reference to Figure 2 One application of the maleic anhydride-based polymer will be described.

[0056] Please refer to Figure 1 With reference to Figure 2 , Figure 1 is a schematic view showing a lens body 10 according to an embodiment, Figure 2is a schematic diagram showing a lens 100 according to an embodiment. The lens 100 comprises a lens body 10 and a hydrophilic coating 20. The lens body 10 can be a hard contact lens or a soft contact lens. The lens body 10 can be a hydrogel contact lens or a silicone hydrogel contact lens. In an embodiment, the lens body 10 is a silicone hydrogel contact lens, a tinted contact lens, a contact lens with a pattern design, an ultraviolet light resistant contact lens, a blue light resistant contact lens, a contact lens for astigmatism, a multifocal contact lens, or a myopia control contact lens, etc. The lens body 10 has an outer surface S. The outer surface S of the lens body 10 comprises an anterior surface 11, a posterior surface 12, and an edge 13. The edge 13 is connected between the anterior surface 11 and the posterior surface 12. The anterior surface 11 is opposite to the posterior surface 12. The edge 13 of the lens body 10 can have a circular shape, an elliptical shape, or any shape. The anterior surface 11 and the posterior surface 12 can be curved surfaces. In Figure 1 an embodiment, the anterior surface 11 is shown as a convex curved surface, and the posterior surface 12 is shown as a concave curved surface, but the present disclosure is not limited thereto. When the lens body 10 is placed on the surface of the eye of a user, the posterior surface 12 of the lens body 10 faces the eye of the user and can directly contact the surface of the eye of the user. The hydrophilic coating 20 is formed at least partially on the outer surface S of the lens body 10. The hydrophilic coating 20 can be formed on at least a portion of the anterior surface 11 and / or at least a portion of the posterior surface 12 of the lens body 10. The hydrophilic coating 20 can cover the outer surface S of the lens body 10. In Figure 2 an embodiment, the hydrophilic coating 20 is shown as covering the anterior surface 11, the posterior surface 12, and the edge 13 of the lens body 10, but the present disclosure is not limited thereto. The hydrophilic coating 20 can be attached on the outer surface S of the lens body 10. Alternatively, a portion of the hydrophilic coating 20 can be attached on the outer surface S of the lens body 10, and another portion of the hydrophilic coating 20 can be formed inside the lens body 10, which can improve the adhesion between the hydrophilic coating 20 and the lens body 10, and can improve the durability of the lens 100. There can be no chemical bonding between the hydrophilic coating 20 and the lens body 10. The hydrophilic coating 20 can be optically transparent.

[0057] The hydrophilic coating 20 comprises a first polymer. The first polymer comprises z first repeating units represented by the above Formula I, m second repeating units represented by the above Formula II, and q fourth repeating units represented by the below Formula IV. Wherein z, m are in the ranges as described above, and q is an integer or a non-integer greater than or equal to 1. R1in Formula IV is H or a substituent comprising at least one of a primary amine group, a secondary amine group, and a tertiary amine group. R2in Formula IV is a substituent comprising at least one of a primary amine group, a secondary amine group, and a tertiary amine group. In the first polymer, R a in the above Formula II is H or C1-C3 alkyl, and R bH or C1-C3 alkyl or another repeat unit, which can be a first repeat unit, a second repeat unit, or a fourth repeat unit. In Formula IV, the line segment extending from inside the parentheses to outside the parentheses represents a bond to another repeat unit, which can be a first repeat unit, a second repeat unit, or a fourth repeat unit. In the first polymer, one or more first repeat units, one or more second repeat units, and one or more fourth repeat units can be randomly bonded to each other.

[0058] [Formula IV]

[0059]

[0060] In one embodiment, q is between 1 and 20, for example, between 5 and 15.

[0061] In one embodiment, at least one of R1and R2in Formula IV can comprise a structure represented by Formula IV-1 or Formula IV-2.

[0062] [Formula IV-1]

[0063]

[0064] [Formula IV-2]

[0065]

[0066] *1 in Formula IV-1 represents a bond to N in the fourth repeat unit; the dashed line represents that the structure represented by Formula IV-1 can extend to a larger structure with similar structures. *2 in Formula IV-2 represents a bond to N in the fourth repeat unit, and x is an integer greater than zero.

[0067] In the first polymer, at least one first repeat unit can be bonded to a second repeat unit, and at least one fourth repeat unit can be bonded to a second repeat unit. In one embodiment, in the first polymer, a plurality of first repeat units can be bonded to each other to form a first chain structure, a plurality of second repeat units can be bonded to each other to form a second chain structure, and a plurality of fourth repeat units can be bonded to each other to form a fourth chain structure, an end first repeat unit in the first chain structure can be bonded to a second repeat unit in the second chain structure, and an end fourth repeat unit in the fourth chain structure can be bonded to a second repeat unit in the second chain structure. In one embodiment, the first polymer can be represented by Formula B below, where z, m, and q are in the ranges described above, and R1and R2are as defined above. In one embodiment, the molar ratio of the second repeat units to the fourth repeat units in the first polymer is between 0.5 and 50, for example, between 2 and 30. In one embodiment, the molar ratio of the second repeat units to the fourth repeat units in the first polymer can be 2.3, 2.5, 3, 8, or 21.

[0068] [Formula B]

[0069]

[0070] The hydrophilic coating 20 can have non-covalent bonding with the lens body 10. The hydrophilic coating 20 can be attached to the lens body 10 through non-covalent bonding between at least one of the R1 and R2 substituents of the fourth repeating unit in the first polymer and the lens body 10. The at least one of the R1 and R2 substituents of the fourth repeating unit in the first polymer can be attached to the lens body 10 through intermolecular forces. The at least one of the R1 and R2 substituents of the fourth repeating unit can stretch into the interior of the lens body 10 and entangle with the lens material, which can improve the adhesion between the hydrophilic coating 20 and the lens body 10, and can improve the durability of the lens 100.

[0071] In an embodiment, in the hydrophilic coating 20, the content of the at least one of the R1 and R2 substituents of the fourth repeating unit in the first polymer decreases along a direction away from the outer surface S of the lens body 10 (e.g., the normal direction D1 of the outer surface S, but the outer surface S can have multiple normal directions, and the normal direction D1 here is only one of the multiple normal directions); the content of the first repeating unit and / or the second repeating unit in the first polymer increases along a direction away from the outer surface S of the lens body 10 (e.g., the normal direction D1 of the outer surface S).

[0072] In an embodiment, the hydrophilic coating 20 has a first side 20S1 facing the outer surface S of the lens body 10 and a second side 20S2 opposite to the first side 20S1. On the first side 20S1 of the hydrophilic coating 20, the content of the fourth repeating unit in the first polymer is greater than the content of the first repeating unit and / or the second repeating unit. On the second side 20S2 of the hydrophilic coating 20, the content of the fourth repeating unit is less than the content of the first repeating unit and / or the second repeating unit.

[0073] The first polymer can be formed by reacting a maleic anhydride-based polymer with an amine-containing polymer. The fourth repeating unit represented by Formula IV in the first polymer can be formed by reacting the third repeating unit represented by Formula III in the maleic anhydride-based polymer with the amine-containing polymer, in which at least a portion of the cyclic structure in the third repeating unit is opened and forms a bond (e.g., a covalent bond) with the amine-containing polymer to form a structure as represented by Formula IV. The fourth repeating unit represented by Formula IV in the first polymer can also be understood to include a residue of the maleic anhydride-based polymer and a residue of the amine-containing polymer, or can be understood as a residue of the maleic anhydride-based polymer bonded to a residue of the amine-containing polymer. The term "residue of the maleic anhydride-based polymer" can mean a moiety derived from the maleic anhydride-based polymer. The term "residue of the amine-containing polymer" can mean a moiety derived from the amine-containing polymer. At least one of the R1and R2substituents of the fourth repeating unit in the first polymer can be derived from the amine-containing polymer. The reaction of the maleic anhydride-based polymer with the amine-containing polymer can include a grafting reaction.

[0074] In an embodiment, the amine-containing polymer can include or be a polyethyleneimine, which is a branched polyethyleneimine and / or a linear polyethyleneimine; at least one of the R1and R2substituents of the fourth repeating unit in the first polymer can be derived from the polyethyleneimine. The branched polyethyleneimine can include a structure represented by the following Formula C-1. The linear polyethyleneimine can include a structure represented by the following Formula C-2.

[0075] [Formula C-1]

[0076]

[0077] [Formula C-2]

[0078]

[0079] Formula C-1 shows only a partial structure of the branched polyethyleneimine, and the dashed line represents that it can extend with similar structures to form a macromolecule. In Formula C-2, x is an integer greater than zero.

[0080] In one embodiment, the method of manufacturing the lens 100 with the hydrophilic coating 20 can include the following steps. The lens body 10 manufactured by any suitable method is sequentially soaked in a first treatment solution including an amine-containing polymer and a second treatment solution including a maleic anhydride-based polymer. The amine-containing polymer and the maleic anhydride-based polymer can be used as described above. The maleic anhydride-based polymer and the amine-containing polymer can react to form a first polymer, and a hydrophilic coating 20 including the first polymer can be formed on the outer surface S of the lens body 10 and / or the interior of the lens 10. In one embodiment, the first treatment solution and the second treatment solution can further include methanol, ethanol, propanol, isopropanol, or acetone and / or deionized water. The soaking time of the lens in the first treatment solution and the soaking time of the lens in the second treatment solution is 30 seconds to 240 minutes, and the temperature of the first treatment solution and the temperature of the second treatment solution is 20°C to 60°C.

[0081] The weight average molecular weight of the amine-containing polymer can be between 1,000 and 1,000,000, or can be between 1,500 and 850,000, or can be between 2,000 and 750,000. If the weight average molecular weight of the amine-containing polymer is too low, the oil and grease adsorption resistance of the lens will be reduced, and if the weight average molecular weight of the amine-containing polymer is too high, the winding effect on the lens body will be affected and the bonding effect with the maleic anhydride-based polymer will also be reduced, thereby affecting the hydrophilicity and oil and grease adsorption resistance of the lens.

[0082] The content of the amine-containing polymer in the first treatment solution can be between 10 ppm and 20,000 ppm, or can be between 100 ppm and 15,000 ppm, relative to the total weight of the first treatment solution. If the content of the amine-containing polymer is too low, the lens requires a longer soaking time. If the content of the amine-containing polymer is too high, the lens will have a whitening phenomenon.

[0083] The weight average molecular weight of the maleic anhydride-based polymer can be between 5,000 and 1,500,000, for example, between 5,000 and 1,000,000 or for example, between 5,000 and 500,000. If the weight average molecular weight of the maleic anhydride-based polymer is too high or too low, the bonding effect of the maleic anhydride-based polymer with the amine-containing polymer will be affected, thereby affecting the properties of the lens.

[0084] The content of the maleic anhydride-based polymer in the second treatment solution can be between 10 ppm and 25,000 ppm, or can be between 100 ppm and 20,000 ppm, relative to the total weight of the second treatment solution. If the content of the maleic anhydride-based polymer is too low, the lens requires a longer soaking time.

[0085] In one embodiment, the method of manufacturing the lens 100 with the hydrophilic coating 20 can further comprise the following steps. After soaking in the second treatment solution, the lens with the hydrophilic coating is removed from the second treatment solution and stored in a buffer solution before being subjected to a process of sterilization by packaging. The buffer solution can be, for example, a phosphate buffered saline. The sterilization conditions are 110°C to 135°C for 3 minutes to 120 minutes.

[0086] Reference is made to Figure 3 . Figure 3 is a schematic view showing a lens 200 according to another embodiment. The lens 200 differs from the lens 100 shown in Figure 2 by comprising a base layer 30 formed between the lens body 10 and the hydrophilic coating 20. The base layer 30 is formed at least partially on the outer surface S of the lens body 10. The base layer 30 can be formed on at least part of the front surface 11 and / or at least part of the back surface 12 of the lens body 10. In Figure 3 , the base layer 30 is shown as covering the front surface 11, the back surface 12 and the edge 13 of the lens body 10, but the present application is not limited thereto. The hydrophilic coating 20 is formed at least partially on the surface of the base layer 30. The base layer 30 can be optically transparent. The base layer 30 comprises a second polymer having carboxyl groups. The second polymer of the base layer 30 can be selected from one of the group consisting of poly(acrylic acid) (PAA), polymethacrylate (PMA), poly(methyl methacrylate) (PMMA) and poly(methacrylic acid) (PMAA). The hydrophilic coating 20 in the lens 200 is not formed inside the lens body 10. In the hydrophilic coating 20 in the lens 200, the R1 and R2 substituents of the fourth repeating unit of the first polymer do not extend into the interior of the lens body 10 and entangle with the lens material.

[0087] In the hydrophilic coating 20 in the lens 200, the content of at least one of the R1 and R2 substituents of the fourth repeating unit of the first polymer decreases in a direction away from the outer surface of the lens body 10, and the content of the first repeating unit and / or the second repeating unit of the first polymer increases in a direction away from the outer surface of the lens body 10. In the hydrophilic coating 20 in the lens 200, the content of the fourth repeating unit of the first polymer is greater than the content of the first repeating unit and / or the second repeating unit on the side of the hydrophilic coating 20 facing the lens body 10. In the hydrophilic coating 20 in the lens 200, the content of the fourth repeating unit of the first polymer is less than the content of the first repeating unit and / or the second repeating unit on the side of the hydrophilic coating 20 facing away from the lens body 10.

[0088] The difference between the manufacturing method of the lens 200 and the manufacturing method of the lens 100 is that the manufacturing method of the lens 200 further comprises: before the lens body 10 is soaked in the first treatment solution, the lens body 10 is soaked in a third treatment solution containing a second polymer. The content of the second polymer in the third treatment solution can be between 10 ppm and 25,000 ppm, or between 100 ppm and 10,000 ppm, relative to the total weight of the third treatment solution. If the content of the second polymer is too low, the anti-lipid adsorption effect of the lens is low. In an embodiment, the soaking time of the lens in the third treatment solution is 30 seconds to 240 minutes. The temperature of the third treatment solution is 20°C to 60°C.

[0089] <Applications of maleic anhydride-based polymers>

[0090] In an embodiment, the maleic anhydride-based polymer can be used to prepare a composition that can be used to manufacture a lens having hydrophilicity. The composition for a lens comprises a maleic anhydride-based polymer and a polymerizable monomer. The content of the maleic anhydride-based polymer can be 0.05wt% to 1wt%, for example 0.1wt%, relative to the total weight of the composition for a lens.

[0091] The polymerizable monomer can comprise a monomer containing an alkenyl group, or a hydrophilic monomer containing an alkenyl group and having hydrophilicity. The polymerizable monomer can comprise at least one of a hydrophilic monomer and a siloxane monomer. The siloxane monomer can comprise one or more different siloxane monomers, for example can comprise at least one of a siloxane monomer having one methacryloyl group, a siloxane monomer having two methacryloyl groups, and a siloxane monomer having three or more methacryloyl groups. The polymerizable monomer can be selected from at least one of the group consisting of a hydrophilic monomer and a siloxane monomer. In an embodiment, the siloxane monomer comprises a siloxane monomer having one methacryloyl group and a siloxane monomer having two methacryloyl groups.

[0092] <Hydrophilic monomers>

[0093] The hydrophilic monomer can be selected from one or more of the group consisting of 2-hydroxyethyl methacrylate (HEMA), methyl methacrylate (MMA), methacrylic acid (MAA), N-vinyl pyrrolidone (NVP), N,N-dimethyl-acrylamide (DMA), 4-acryloylmorpholine (AcMO), 2-hydroxyethyl acrylamide (HEAA), glycidylmethacrylate (GMA), glycerol mono-methacrylate (GMMA), acrylic acid (AA), N,N-di(methyl methacryl-amide) (DMA), hexafluoroisopropyl methacrylate (HFMA), N-vinyl-N-methyl acetamide, glycine vinylcarbonate, 2-methacryloyloxyethylphosphorylcholine, and 2-hydroxy-butyl methacrylate.

[0094] <silicone monomer>

[0095] A methacryloyl group can be represented as CH2=C(CH3)CO-; alternatively, a methacryloyl group can be represented as

[0096] The silicone monomer having a single methacryloyl group can be selected from one or more of the group consisting of silicone monomers represented by the following Formula 1A to the following Formula 1H.

[0097] [Formula 1A]

[0098]

[0099] [Formula 1B]

[0100]

[0101] In Formula 1B, aa = 4 ~ 80.

[0102] [Formula 1C]

[0103]

[0104] In Formula 1C, bb = 4 ~ 80, cc = 3 ~ 40.

[0105] [Formula 1D]

[0106]

[0107] In Formula 1D, dd = 2 ~ 40, ee = 2 ~ 40.

[0108] [Formula 1E]

[0109]

[0110] In Formula 1E, ff = 2 ~ 40, gg = 2 ~ 40.

[0111] [Formula 1F]

[0112]

[0113] In Formula 1F, hh = 4 ~ 80.

[0114] [Formula 1G]

[0115]

[0116] In Formula 1G, ii = 4 ~ 80.

[0117] [Formula 1H]

[0118]

[0119] In Formula 1H, TMS is an abbreviation for trimethylsiloxane.

[0120] The second siloxane monomer having two methacryl groups can be selected from one or more of the group consisting of siloxane monomers represented by the following Formula 2A to the following Formula 2C.

[0121] [Formula 2A]

[0122]

[0123] In Formula 2A, jj = 4 ~ 80, kk = 1 ~ 10, rr = 1 ~ 10.

[0124] [Formula 2B]

[0125]

[0126] In Formula 2B, ss = 4-80.

[0127] [Formula 2C]

[0128]

[0129] In Formula 2C, tt = 4-80.

[0130] In one embodiment, the content of the siloxane monomer having one methacryl group can be 50wt% to 91wt% and the content of the siloxane monomer having two methacryl groups can be 9wt% to 50wt% relative to the total weight of the siloxane monomer.

[0131] In one embodiment, the composition for the lens can further comprise an ultraviolet light absorber, and / or an initiator, and / or a blue light absorber. The ultraviolet light absorber can be selected from the ultraviolet light absorbers known in the art that can be applied to contact lens materials. The content of the ultraviolet light absorber can be 0.01wt% to 5wt% relative to the total weight of the composition for the lens. The initiator can be a thermal initiator or a photo initiator. The thermal initiator and the photo initiator can be selected from the initiators known in the art that can be applied to polymerization reactions. The content of the initiator can be 0.45wt% to 0.75wt% relative to the total weight of the composition for the lens. The kind and the amount of the blue light absorber to be added can be selected by those skilled in the art according to the actual needs. For example, the blue light absorber can be Reactive Yellow 15. In one embodiment, the content of the blue light absorber can be 0.1wt% to 5wt% relative to the total weight of the composition for the lens.

[0132] The above-mentioned components can be mixed in a specific ratio to form the composition for the lens. In one embodiment, the composition for the lens can be placed in a contact lens mold and cured by heating or light to form the lens by the curing reaction (thermal curing reaction or photo curing reaction) of the components in the composition. The heating temperature can be about 30-150°C and the heating time can be about 1-12 hours. After the curing reaction, hydration treatment and / or sterilization can be performed. The hydration treatment can include soaking the lens in alcohol and pure water and then placing the lens in a buffer solution for equilibration.

[0133] <Use of maleic anhydride-based polymer>

[0134] In one embodiment, the maleic anhydride-based polymer can be used to prepare a treatment agent having hydrophilicity, which can be used for a lens. The treatment agent for a lens is, for example, a packaging solution for a lens (a delivery solution for a lens), a cleaning solution for a lens, a maintenance solution for a lens, or a disinfectant for a lens, and the like. The packaging solution for a lens refers to a solution stored in a packaging container together with a lens. A lens is usually stored in a packaging container containing a packaging solution for sale. The packaging solution for a lens can be a buffer solution. When a lens contacts a treatment agent, the treatment agent enters the inside of the lens or adheres to the surface of the lens to affect the degree of moisture retention and the degree of comfort of the lens.

[0135] The treatment agent for a lens contains at least a buffer solution and a maleic anhydride-based polymer. The treatment agent can contain 0.05 to 5% by weight of the maleic anhydride-based polymer, for example, 0.1 to 2% by weight, relative to the total weight of the treatment agent. The buffer solution can contain one or more of boric acid or a salt thereof, tromethamine, citric acid or a salt thereof, phosphoric acid or a salt thereof, tartaric acid or a salt thereof, gluconic acid or a salt thereof, acetic acid or a salt thereof, carbonic acid or a salt thereof, and an amino acid.

[0136] In one embodiment, the treatment agent can further contain a moisturizing lubricant, a vitamin, an osmotic pressure adjusting agent, a surfactant, a cooling agent, or any combination thereof. The moisturizing lubricant can be selected from one or more of the group consisting of methylcellulose (MC), hydroxypropyl methylcellulose (HPMC), hydroxyethyl cellulose, carboxymethyl cellulose (CMC), hyaluronic acid (HA), a hyaluronate, alginic acid, an alginate, a phosphorylcholine group-containing polymer, polyvinylpyrrolidone (PVP), and polyglucose. The phosphorylcholine group-containing polymer can be, for example, poly[2-methacryloyloxyethylphosphorylcholine] (poly-MPC), a copolymer of 2-methacryloyloxyethylphosphorylcholine (MPC) and methacrylic acid ester, or a combination thereof. The content of the moisturizing lubricant can be 0.01 to 1% by weight, relative to the total weight of the treatment agent.

[0137] The vitamin can be one or more selected from the group consisting of vitamin A, vitamin B, vitamin C, vitamin D, vitamin E and vitamin K. The vitamin B can be one or more selected from the group consisting of vitamin Bl, vitamin B2, vitamin B3, vitamin B6 and vitamin B 12. The content of the vitamin can be 0.001 wt% to 1 wt%, for example, 0.001 wt% to 0.5 wt%, relative to the total weight of the treating agent. The osmotic pressure regulator can be one or more selected from the group consisting of sodium chloride, potassium chloride, calcium chloride, zinc chloride, magnesium chloride and dextrose. The content of the osmotic pressure regulator can be 0.01 wt% to 2.5 wt%, relative to the total weight of the treating agent. The osmotic pressure regulator can adjust the osmotic pressure of the treating agent so that the osmotic pressure thereof is close to the osmotic pressure of normal tear. The surfactant can be one or more selected from the group consisting of nonionic surfactant, cationic surfactant and zwitterionic surfactant. The type and usage amount of the surfactant can be selected by those skilled in the art according to actual needs. For example, the content of the surfactant can be 0.0001 wt% to 5.0 wt%, relative to the total weight of the treating agent. The type and usage amount of the cooling agent can be selected by those skilled in the art according to actual needs. For example, the content of the cooling agent can be 0.0001 wt% to 1.0 wt%, relative to the total weight of the treating agent.

[0138] In an embodiment, the treating agent can further comprise a pharmaceutically effective ingredient, such as a vasoconstrictor, an anti-inflammatory agent, an astringent, an anti-allergic ingredient, an antibacterial agent or any combination thereof. The content of the pharmaceutically effective ingredient can be 0.001 wt% to 5.0 wt%, relative to the total weight of the treating agent.

[0139] In an embodiment, the treating agent comprises a maleic anhydride-based polymer, vitamin B, a polymer having a choline phosphate group and deionized water. The simultaneous presence of vitamin B and the polymer having a choline phosphate group in the treating agent can improve the moisturizing degree and comfort level of the lens.

[0140] The above-mentioned ingredients can be added to deionized water in a specific ratio, mixed uniformly to obtain a treating agent for lenses.

[0141] In order to make the above-mentioned objects, features and advantages of the present application more obvious and easy to understand, specific examples are given below for detailed description as follows:

[0142] <Maleic anhydride-based polymer>

[0143] A maleic anhydride-based polymer (hereinafter also referred to as product) was produced according to the components and proportions described in Table 1 below using the production method described above. The examples and comparative examples of Table 1 use maleic anhydride as the maleic anhydride-containing compound. The content of the third repeating unit refers to the proportion of the third repeating unit in the total weight of the product. The product was added to a predetermined amount of water at a proportion of 1% and the solubility was observed visually and the content of the third repeating unit was determined by titration.

[0144] The symbol represents that the product is soluble in water and the solution is transparent, and the symbol represents that the product is not completely soluble in water and the solution is white and turbid.

[0145] [Table 1]

[0146]

[0147] Comparative Example 1 uses maleic anhydride to form polymaleic anhydride (i.e. a polymer that is not modified with poly(ethylene glycol) methacrylate) and tests its solubility in water, and the results show that it has poor solubility and precipitates. In Comparative Example 2, the amount of the maleic anhydride-containing compound is too high, and the product formed has poor solubility in water and precipitates, and the content of the third repeating unit cannot be determined by titration due to the precipitation. The maleic anhydride-based polymers of Examples 1 to 5 are all soluble in water without precipitation or turbidity, which indicates that the use of poly(ethylene glycol) methacrylate to modify the product at a specific proportion can effectively improve the solubility. Moreover, the use of poly(ethylene glycol) methacrylate to modify the product does not open the cyclic structure of the maleic anhydride functional group, so the reactivity of the maleic anhydride functional group can be maintained. The ring-opened maleic anhydride functional group will be difficult to bond with other materials (such as an amine-containing polymer) in subsequent hydrophilic coating processes, so that a stable hydrophilic coating cannot be formed.

[0148] In addition to visual observation, a dynamic light scattering (DLS) instrument can also be used to detect the transmittance (%) of the product aqueous solution (the product is added to a predetermined amount of water at a proportion of 1% to form the product aqueous solution), and the results show that the product aqueous solution of the examples has a transmittance of 86% or more, and the product aqueous solution of Comparative Example 2 has a transmittance of less than 86%, indicating that the solubility of the product of the examples in water is better than that of the product of the comparative examples.

[0149] [Contact lenses with hydrophilic coatings]

[0150] The maleic anhydride-based polymers of Examples 1-5 were prepared according to the components and proportions described in Table 1 using the aforementioned preparation method. The maleic anhydride-based polymers of Examples 1-5 were then used in the aforementioned method for preparing a lens with a hydrophilic coating to prepare lenses with a hydrophilic coating of Examples 1A-5B. The components used in the method for preparing a lens with a hydrophilic coating are shown in Table 2 below. Examples 1A and 1B used the maleic anhydride-based polymer of Example 1, and the lenses of Example 1B further included a base layer. Examples 2A and 2B used the maleic anhydride-based polymer of Example 2, and the lenses of Example 2B further included a base layer. Examples 3A and 3B used the maleic anhydride-based polymer of Example 3, and the lenses of Example 3B further included a base layer. Examples 4A and 4B used the maleic anhydride-based polymer of Example 4, and the lenses of Example 4B further included a base layer. Examples 5A and 5B used the maleic anhydride-based polymer of Example 5, and the lenses of Example 5B further included a base layer. Comparative Example 3 was a lens that did not include a hydrophilic coating or a base layer (an untreated lens). The lenses of the Examples and Comparative Example of Table 2 used the same components as the lens body.

[0151] [Table 2]

[0152]

[0153]

[0154] The method and conditions used in the Examples and Comparative Example of Table 2 are as follows. The amine-containing polymer was dissolved in ethanol and deionized water, and mixed to form a first treatment solution. The maleic anhydride-based polymer was dissolved in deionized water, and mixed to form a second treatment solution. The second polymer was dissolved in ethanol and deionized water, and mixed to form a third treatment solution. The lens body was immersed in the first treatment solution for 60 to 120 minutes. The lens body was removed from the first treatment solution, and then immersed in the second treatment solution for 60 to 120 minutes. The lens structure including the hydrophilic coating and the lens was removed from the second treatment solution, and stored in a buffer solution for a packaging sterilization process. The sterilization conditions were 125°C for 50 minutes. Examples 1B, 2B, 3B, 4B, and 5B further included immersing the lens body in the third treatment solution for 60 to 120 minutes before immersing the lens body in the first treatment solution.

[0155] The lenses of Examples 1A-5B and Comparative Example 3 were tested for water contact angle, and the results are shown in Table 2 above.

[0156] [Water Contact Angle Test]

[0157] The lens was placed on a non-woven cloth, and the lens structure was pressed for 10 seconds through the non-woven cloth to remove the moisture on the lens surface, and then a contact angle measuring instrument (model DSA25) was used to detect the angle between the water droplet surface and the lens surface (water contact angle). The greater the water contact angle, the more hydrophobic the lens surface; the smaller the water contact angle, the more hydrophilic the lens surface.

[0158] The water contact angles of the lenses of Examples 1A to 5B were all smaller than that of the lens of Comparative Example 3, indicating that the lens surface of the present application has high hydrophilicity. The lenses of Examples 2B, 3B and 4B all have a water contact angle of 60° or less, indicating that the base layer can further improve the hydrophilicity of the lens. In addition, the lenses of Examples 1B, 2B, 3B, 4B and 5B were subjected to dyeing tests using Sudan dye solution, and the test results showed that the lenses of Examples 1B, 2B, 3B, 4B and 5B were not dyed or were lightly dyed by the Sudan dye solution, indicating that the base layer can improve the oil adsorption resistance of the lens. As can be seen from Table 2, the lens surface of the present application has high hydrophilicity and oil adsorption resistance, which can effectively improve the wearing comfort of the user and can improve the dryness, infection, eye damage and other conditions of the user.

[0159] <Processing agent for lenses>

[0160] The components described in Table 3 were mixed in the proportions in the table, stirred until uniform and no undissolved substances were observed in the solution to the naked eye, to prepare a processing agent for lenses. The maleic anhydride-based polymer in Table 3 was the maleic anhydride-based polymer of Example 1, and deionized water was used as the solvent. 1 mL of the processing agent for lenses was placed in a packaging container, the lens was immersed in the processing agent in the packaging container, an aluminum foil was heat-sealed on the packaging container and then subjected to a sterilization process, and the sterilization conditions were as described above. The lenses of Examples 6 to 10 and Comparative Example 4 were subjected to water contact angle detection, and the results are shown in Table 3. The processing agent shown in Examples 6 to 10 can be used as a packaging solution for lenses.

[0161] [Table 3]

[0162]

[0163] As can be seen from Table 3, the water contact angles of the lenses of Examples 6 to 10 were all smaller than that of the lens of Comparative Example 4, indicating that storing the lens in the processing agent of the present application can improve the hydrophilicity of the lens surface and improve the wearing comfort of the user.

[0164] <Composition for lenses>

[0165] ​In Example 11, the composition for the lens includes 0.1 wt% of the maleic anhydride-based polymer (relative to the total weight of the composition) and the hydrophilic monomer and the siloxane monomer. In Comparative Example 5, the composition for the lens includes only the hydrophilic monomer and the siloxane monomer without the maleic anhydride-based polymer. Example 11 and Comparative Example 5 use the same hydrophilic monomer and the siloxane monomer, and the compositions for the lenses are made using the aforementioned manufacturing method. The compositions for the lenses of Example 11 and Comparative Example 5 are placed in the contact lens mold, and the lenses are made using the aforementioned manufacturing method. The lenses are subjected to the water contact angle test (the water contact angle test is performed in the manner described above), and the water contact angle of the lens of Example 11 is 82°, and the water contact angle of the lens of Comparative Example 5 is 85°, indicating that the use of the maleic anhydride-based polymer of the present application in the composition for the lens can effectively improve the hydrophilicity of the lens surface.

[0166] Therefore, the maleic anhydride-based polymer of the present application can effectively improve the solubility of the maleic anhydride-based polymer and maintain the reactivity of the maleic anhydride functional group. The lens, the treating agent for the lens, and the composition for the lens of the present application can effectively improve the hydrophilicity and the oil adsorption resistance, improve the wearing comfort, and reduce the problem of the clarity caused by the oil adhering to the lens surface, and have the advantages of simple manufacturing process, low cost, high yield, and the like.

[0167] Although the present application has been disclosed with reference to the preferred embodiments, it is not intended to limit the present application, and any person skilled in the art can make some modifications and improvements without departing from the spirit and scope of the present application, and therefore the scope of protection of the present application is defined by the claims.

Claims

1. A maleic anhydride-based polymer comprising: one or more first repeating units represented by the following Formula I; one or more second repeating units represented by the following Formula II; and one or more third repeating units represented by the following formula III, wherein R a is H or C1-C3 alkyl, and R b is H or C1-C3 alkyl or the first repeating unit or the second repeating unit or the third repeating unit, [Formula I] [Formula II] [Formula III] 2. The maleic anhydride-based polymer of claim 1, wherein, a content of the third repeating unit is 0.5 wt% to 9 wt% based on a total weight of the maleic anhydride-based polymer.

3. The maleic anhydride-based polymer of claim 1, wherein, a molar ratio of the second repeating unit to the third repeating unit is 0.5 to 50.

4. The maleic anhydride-based polymer of claim 1, wherein, the maleic anhydride-based polymer comprises z of the first repeating units, m of the second repeating units, and p of the third repeating units, z is between 4 and 50, m is between 10 and 50, and p is between 1 and 20.

5. The maleic anhydride-based polymer of claim 1, wherein, the first repeating unit is bonded to the second repeating unit, and the third repeating unit is bonded to the second repeating unit.

6. The maleic anhydride-based polymer of claim 1, wherein, the maleic anhydride-based polymer is represented by the following Formula A: [Formula A] wherein z is between 4 and 50, m is between 10 and 50, and p is between 1 and 20.

7. An ophthalmic lens having a hydrophilic coating comprising: an ophthalmic lens body; and a hydrophilic coating formed at least partially on an outer surface of the ophthalmic lens body, wherein the hydrophilic coating comprises a first polymer, the first polymer comprising: one or more first repeating units represented by the following Formula I: one or more second repeating units represented by the following Formula II; and one or more fourth repeating units represented by the following formula IV, R1in formula IV is H or a substituent comprising at least one of a primary amine group, a secondary amine group, and a tertiary amine group, R2in formula IV is a substituent comprising at least one of a primary amine group, a secondary amine group, and a tertiary amine group, R a is H or C1-C3 alkyl, R b is H or C1-C3 alkyl or the first repeating unit or the second repeating unit or the fourth repeating unit, [Formula I] [Formula II] [Formula IV] 8. The lens having a hydrophilic coating according to claim 7, wherein, a molar ratio of the second repeating unit to the fourth repeating unit is 0.5 to 50.

9. The lens having a hydrophilic coating according to claim 7, wherein, the polymer comprises z of the first repeating units and m of the second repeating units, z is between 4 and 50, and m is between 10 and 50.

10. The lens having a hydrophilic coating according to claim 7, wherein, further comprising a primer layer formed between the ophthalmic lens body and the hydrophilic coating, wherein the primer layer comprises a second polymer, the second polymer having a carboxyl group.

11. The lens having a hydrophilic coating according to claim 7, wherein, the first polymer is represented by the following Formula B: [Formula B] wherein z is between 4 and 50, m is between 10 and 50, and q is between 1 and 20.

12. A treatment agent for an ophthalmic lens comprising a buffer solution and the maleic anhydride-based polymer of claim 1.

13. The treatment of claim 12, wherein, further comprising at least one of a humectant lubricant and a vitamin.

14. The treatment of claim 12, wherein, the treatment agent comprises 0.05 wt% to 5 wt% of the maleic anhydride-based polymer relative to a total weight of the treatment agent.

15. A composition for an ophthalmic lens comprising: the maleic anhydride-based polymer of claim 1 and a polymerizable monomer.

16. The composition of claim 15, wherein the polymerizable monomer comprises at least one of a hydrophilic monomer and a siloxane monomer.

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