Maleic anhydride-based polymer, lens having hydrophilic layer, lens treating agent, and lens composition

Abstract

To provide a maleic anhydride-based polymer, a lens having a hydrophilic layer, a treating agent for the lens, and a composition for the lens which improve the hydrophilic property and stability of the hydrophilic layer to improve the wearing comfort of a user.SOLUTION: The polymer includes one or more first repeat units represented by the following Chemical Formula I, one or more second repeat units represented by the following Chemical Formula II, and one or more third repeat units represented by the following Chemical Formula III. In Formula II, Ra is H or a C1 to C3 alkyl group and Rb is H or a C1 to C3 alkyl group or one or more first repeat unit or one or more second repeat unit or one or more third repeat unit.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present disclosure relates to maleic anhydride-based polymers, lenses having a hydrophilic layer, lens treatments, and lens compositions. [Background technology]

[0002] Compounds containing maleic anhydride are common materials that can improve hydrophilicity and can be used to form hydrophilic layers, contact lenses, contact lens treatment agents, etc. However, due to the low solubility of maleic anhydride, suspended particles are formed in the solution, resulting in a visibly cloudy white appearance. The low solubility of maleic anhydride complicates the manufacturing process and reduces its reactivity with other materials, ultimately resulting in lower quality products. Summary of the Invention [Problem to be solved by the invention]

[0003] The present disclosure relates to a maleic anhydride-based polymer and a lens having a hydrophilic layer. The present disclosure modifies a maleic anhydride-containing compound to improve solubility, thereby improving the hydrophilicity and stability of the hydrophilic layer and improving wear comfort for the user. Meanwhile, the lens exhibits excellent resistance to lipid adsorption. The present disclosure relates to a lens treatment agent and a lens composition. These treatment agents and compositions include a maleic anhydride-based polymer to improve the hydrophilicity of the lens, thereby improving wear comfort for the user. [Means for solving the problem]

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

[0005] [Chemical formula I] JPEG2026012049000001.jpg2917

[0006] [Chemical formula II] JPEG2026012049000002.jpg3925

[0007] [Chemical formula III] JPEG2026012049000003.jpg2532

[0008] According to an embodiment of the present disclosure, a lens having a hydrophilic layer is provided. The lens having a hydrophilic layer includes a lens body and the hydrophilic layer. The hydrophilic layer is on at least a portion of the outer surface of the lens body. The hydrophilic layer includes a first polymer. The first polymer includes one or more first repeating units represented by the following chemical formula I, one or more second repeating units represented by the following chemical formula II, and one or more fourth repeating units represented by the following chemical formula IV. In chemical formula IV, R1 is H or a substituent containing at least one of a primary amine group, a secondary amine group, and a tertiary amine group. In chemical formula IV, R2 is a substituent containing at least one of a primary amine group, a secondary amine group, and a tertiary amine group. In chemical formula II, R a is H or a C1-C3 alkyl group, and Rb is H or a C1-C3 alkyl group or one or more first repeat units or one or more second repeat units or one or more fourth repeat units.

[0009] [Chemical formula I] JPEG2026012049000004.jpg2917

[0010] [Chemical formula II] JPEG2026012049000005.jpg3925

[0011] [Chemical formula IV] JPEG2026012049000006.jpg3633

[0012] According to an embodiment of the present disclosure, there is provided a lens treatment agent, the treatment agent comprising a buffer and a maleic anhydride-based polymer.

[0013] According to an embodiment of the present disclosure, there is provided a lens composition, the composition comprising a maleic anhydride-based polymer and a polymerizable monomer.

[0014] These and other embodiments of the present disclosure will become better understood with regard to the following detailed description of non-limiting embodiments, the following description being made with reference to the accompanying drawings. [Brief explanation of the drawings]

[0015] [Figure 1] 1 shows a schematic diagram of a lens body according to an embodiment of the present disclosure. [Figure 2] 1 shows a schematic diagram of a lens according to an embodiment of the present disclosure. [Figure 3] 1 shows a schematic diagram of a lens according to another embodiment of the present disclosure. DETAILED DESCRIPTION OF THE INVENTION

[0016] The illustrations may not necessarily be drawn to scale, and there may be other embodiments of the present disclosure that are not clearly illustrated. Therefore, the specification and drawings should be regarded as illustrative rather than restrictive. Furthermore, the disclosed descriptions of the embodiments of the present disclosure, such as detailed configurations, manufacturing steps, and material selection, are for illustrative purposes only and are not intended to limit the scope of the present disclosure. The steps and elements in the details of these embodiments can be improved or changed according to the actual needs of practical application. It is expected that elements and features of one embodiment can be advantageously incorporated into another embodiment without further elaboration. The present disclosure is not limited to the descriptions of these embodiments. In the illustrations, the same / similar symbols are used to indicate the same / similar elements.

[0017] As used in the specification and the appended claims, ordinal numbers such as "first," "second," etc. to describe elements do not imply or represent a particular location in the structure, order of arrangement, or order of fabrication. These ordinal numbers are merely used to clearly distinguish between multiple elements or components of the same name.

[0018] Maleic anhydride-based polymers and methods for producing same

[0019] A maleic anhydride-based polymer according to the present disclosure includes z first repeat units represented by the following formula I, m second repeat units represented by the following formula II, and p third repeat units represented by the following formula III, where z, m, and p are integers or non-integers greater than or equal to 1. In formula I, a line segment extending from inside the brackets to outside the brackets represents a bond to another repeat unit (which may be the first repeat unit, the second repeat unit, or the third repeat unit) or to another functional group. In formula II, R a is H or a C1-C3 alkyl group, and R bis H or a C1-C3 alkyl group or a first repeat unit or a second repeat unit or a third repeat unit. In Formula III, the line segment extending from inside the brackets to outside the brackets represents a bond to another repeat unit (which may be a first repeat unit, a second repeat unit, or a third repeat unit) or another functional group. In maleic anhydride-based polymers, one or more first repeat units, one or more second repeat units, and one or more third repeat units may be randomly bonded to each other.

[0020] [Chemical formula I] JPEG2026012049000007.jpg2917

[0021] [Chemical formula II] JPEG2026012049000008.jpg3925

[0022] [Chemical formula III] JPEG2026012049000009.jpg2532

[0023] In embodiments, the molar ratio of the second repeat unit to the third repeat unit in the maleic anhydride-based polymer is in the range of 0.5 to 50, such as in the range of 2 to 30. In embodiments, the molar ratio of the second repeat unit to the third repeat unit in the maleic anhydride-based polymer can be 2.3, 2.5, 3, 8, or 21.

[0024] In an embodiment, z is in the range of 4 to 50, for example, in the range of 7 to 11. In an embodiment, m is in the range of 10 to 50, for example, in the range of 20 to 45 or in the range of 30 to 40. In an embodiment, p is in the range of 1 to 20, for example, in the range of 5 to 15. The amount of the third repeat unit can be in the range of 0.5 wt% (weight percent concentration) to 9 wt%, for example, 0.8 wt% to 8 wt% or 2.5 wt% to 7.4 wt%, based on the total weight of the maleic anhydride-based polymer. If the amount of the third repeat unit is too low, the maleic anhydride-based polymer will be less reactive in forming a hydrophilic layer. If the amount of the third repeat unit is too high, the maleic anhydride-based polymer will have low solubility in water, and precipitation may occur.

[0025] The weight average molecular weight (Mw) of the maleic anhydride-based polymer is in the range of 5,000 to 1,500,000, for example, in the range of 5,000 to 1,000,000 or in the range of 5,000 to 500,000. The infrared spectrum of the maleic anhydride-based polymer has a peak at 1780 cm -1 At least one absorption peak near 1728 cm -1 It shows at least one absorption peak in the vicinity.

[0026] In the maleic anhydride-based polymer, at least one first repeat unit can be bonded to a second repeat unit, and at least one third repeat unit can be bonded to the second repeat unit. In an embodiment, in the maleic anhydride-based 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, a plurality of third repeat units can be bonded to each other to form a third chain structure, a first repeat unit at an end of the first chain structure can be bonded to a second repeat unit in the second chain structure, and a third repeat unit at an end of the third chain structure can be bonded to a second repeat unit in the second chain structure. In an embodiment, the maleic anhydride-based polymer is represented by the following chemical formula A, where the ranges of z, m, and p in chemical formula A are as described above.

[0027] [Chemical formula A] JPEG2026012049000010.jpg6256

[0028] Methods for producing maleic anhydride-based polymers are described below with reference to the above embodiments. However, the present disclosure is not limited to these examples. Maleic anhydride-based polymers can be formed by other manufacturing methods.

[0029] The maleic anhydride-based polymer can be formed by reacting a maleic anhydride-containing compound with polyethylene glycol dimethacrylate (PEGMA). In an embodiment, a method for producing the maleic anhydride-based polymer can include the following steps: adding a maleic anhydride-containing compound, polyethylene glycol dimethacrylate, and an initiator into a solvent to form a material solution; and stirring the material solution under a nitrogen atmosphere to promote the reaction between the maleic anhydride-containing compound and the polyethylene glycol dimethacrylate to form the maleic anhydride-based polymer. The initiator can include or be a photoinitiator or a thermal initiator.

[0030] The types and amounts of the photoinitiator and thermal initiator can be selected by those skilled in the art according to actual needs. The solvent can be methanol, ethanol, acetone, dimethyl sulfoxide, dimethylformamide, tetrahydrofuran, N-methyl-2-pyrrolidone, or dimethylacetamide. The maleic anhydride-containing compound can include maleic anhydride or can be maleic anhydride.

[0031] The method for producing maleic anhydride-based polymers can include heating and irradiating the above-mentioned material solution with light, and / or a concentration process under reduced pressure, and / or washing the product with a washing solution. The method for producing maleic anhydride-based polymers can be understood as modification of maleic anhydride-containing compounds with polyethylene glycol dimethacrylate. The method for producing maleic anhydride-based polymers can include radical polymerization.

[0032] <Applications of maleic anhydride-based polymers>

[0033] The maleic anhydride-based polymer according to the present disclosure can be applied to various products, such as hydrophilic layers, hydrophilic lenses, and hydrophilic treatments, to improve hydrophilicity. In an embodiment, the maleic anhydride-based polymer can be used in a hydrophilic layer in a lens. One application of the maleic anhydride-based polymer is described below with reference to Figures 1 and 2.

[0034] 1 and 2, FIG. 1 shows a schematic diagram of a lens body 10 according to an embodiment of the present disclosure, and FIG. 2 shows a schematic diagram of a lens 100 according to an embodiment of the present disclosure. The lens 100 includes a lens body 10 and a hydrophilic layer 20. The lens body 10 can be a hard or soft contact lens. The lens body 10 can be a hydrogel or silicone hydrogel contact lens. In an embodiment, the lens body 10 is a silicone hydrogel contact lens, a colored contact lens, a contact lens with a pattern design, a UV-blocking contact lens, a blue-light-blocking contact lens, a contact lens for astigmatism, a progressive contact lens, or a contact lens for myopia. The lens body 10 includes an outer surface S. The outer surface S of the lens body 10 includes a front surface 11, a back surface 12, and an edge 13. The edge 13 connects the front surface 11 and the back surface 12. The front surface 11 faces the back surface 12. The edge 13 of the lens body 10 can have a circular shape, an elliptical shape, or any other shape. The front surface 11 and the back surface 12 can be curved. In FIG. 1, the front surface 11 is illustrated as a convex surface and the back surface 12 is illustrated as a concave surface, but the present disclosure is not limited thereto. When the lens body 10 is placed on the surface of a user's eye, the back surface 12 of the lens body 10 faces the user's eye and can directly contact the surface of the user's eye. A hydrophilic layer 20 can be formed on at least a portion of the outer surface S of the lens body 10. The hydrophilic layer 20 can be formed on at least a portion of the front surface 11 of the lens body 10 and / or on at least a portion of the back surface 12 of the lens body 10. The hydrophilic layer 20 can cover the outer surface S of the lens body 10. In FIG. 2, the hydrophilic layer 20 is illustrated as covering the front surface 11, back surface 12, and edge 13 of the lens body 10, but the present disclosure is not limited thereto. The hydrophilic layer 20 may be attached to the outer surface S of the lens body 10. Alternatively, a portion of the hydrophilic layer 20 may be attached to the outer surface S of the lens body 10, and another portion of the hydrophilic layer 20 may be formed on the inside of the lens body 10, which can improve adhesion between the hydrophilic layer 20 and the lens body 10 and can improve the durability of the lens 100.There may be no chemical bond between the hydrophilic layer 20 and the lens body 10. The hydrophilic layer 20 may be optically transparent.

[0035] The hydrophilic layer 20 includes a first polymer. The first polymer includes z first repeating units represented by the above chemical formula I, m second repeating units represented by the above chemical formula II, and q fourth repeating units represented by the following chemical formula (IV), where the ranges of z and m are as described above, and q is an integer or non-integer of 1 or greater. In chemical formula IV, R1 is H or a substituent containing at least one of a primary amine group, a secondary amine group, and a tertiary amine group. In chemical formula IV, R2 is a substituent containing at least one of a primary amine group, a secondary amine group, and a tertiary amine group. In the first polymer, R in chemical formula II a is H or a C1-C3 alkyl group, and R in Formula II b is H or a C1-C3 alkyl group or another repeat unit, which may be a first repeat unit, a second repeat unit, or a fourth repeat unit. In Formula IV, the line segment extending from inside the brackets to outside the brackets represents a bond to another repeat unit (which may be a first repeat unit, a second repeat unit, or a fourth repeat unit) or another functional group. In the first polymer, one or more first repeat units, one or more second repeat units, and one or more fourth repeat units may be randomly bonded to one another.

[0036] [Chemical formula IV] JPEG2026012049000011.jpg3633

[0037] In an embodiment, q is in the range of 1-20, for example, in the range of 5-15.

[0038] In embodiments, at least one of R1 and R2 in formula IV can include a structure represented by formula IV-1 or IV-2 below.

[0039] [Chemical formula IV-1] JPEG2026012049000012.jpg5160

[0040] [Chemical formula IV-2] JPEG2026012049000013.jpg2551

[0041] In the chemical formula (IV-1), the symbol * 1 represents a chemical bond with N in the fourth repeat unit. The dotted line indicates that the structure represented by chemical formula IV-1 can be expanded to a larger structure with a similar bonding method. In chemical formula (IV-2), the symbol * 2 represents a chemical bond to N in the fourth repeat unit, and x is an integer greater than 0.

[0042] 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 the second repeat unit. In an 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, a plurality of fourth repeat units can be bonded to each other to form a fourth chain structure, a first repeat unit at an end of the first chain structure can be bonded to a second repeat unit in the second chain structure, and a fourth repeat unit at an end of the fourth chain structure can be bonded to a second repeat unit in the second chain structure. In an embodiment, the first polymer can be represented by the following chemical formula B, where the ranges of z, m, and q in chemical formula B are as described above, and R1 and R2 in chemical formula B are as described above. In embodiments, the molar ratio of the second repeat unit to the fourth repeat unit in the first polymer is in the range of 0.5 to 50, for example, in the range of 2 to 30. In embodiments, the molar ratio of the second repeat unit to the fourth repeat unit in the first polymer can be 2.3, 2.5, 3, 8, or 21.

[0043] [Chemical formula B] JPEG2026012049000014.jpg6254

[0044] A non-covalent bond may exist between the hydrophilic layer 20 and the lens body 10. The hydrophilic layer 20 can be attached to the lens body 10 through a non-covalent bond between at least one of R1 and R2 of the fourth repeat unit and the lens body 10. At least one of R1 and R2 of the fourth repeat unit in the first polymer can be attached to the lens body 10 through intermolecular forces. At least one of R1 and R2 of the fourth repeat unit can extend into the lens body 10 and entangle with the material of the lens body 10, thereby strengthening the bond between the hydrophilic layer 20 and the lens body 10 and improving the durability of the lens 10.

[0045] In an embodiment, in the hydrophilic layer 20, the amount of at least one of R1 and R2 of the fourth repeat unit in the first polymer decreases along a direction away from the outer surface S of the lens body 10 (e.g., along a normal direction D1 of the outer surface S; the outer surface S may have multiple normal directions, and the normal direction D1 is one of these multiple normal directions), and the amount of the first repeat unit and / or the second repeat unit increases along a direction away from the outer surface S of the lens body 10 (e.g., along a normal direction D1 of the outer surface S).

[0046] In the embodiment, the hydrophilic layer 20 includes a first surface 20S1 facing the outer surface S of the lens body 10 and a second surface 20S2 opposite to the first surface 20S1. On the first surface 20S1 of the hydrophilic layer 20, the amount of the fourth repeat unit in the first polymer is greater than the amount of the first repeat unit and / or the second repeat unit in the first polymer. On the second surface 20S2 of the hydrophilic layer 20, the amount of the fourth repeat unit in the first polymer is less than the amount of the first repeat unit and / or the second repeat unit in the first polymer.

[0047] The first polymer can be formed by reacting a maleic anhydride-based polymer with an amine-containing polymer. The fourth repeat unit represented by Formula IV in the first polymer can be formed by reacting the third repeat unit represented by Formula III in the maleic anhydride-based polymer with an amine-containing polymer, wherein at least a portion of the cyclic structure of the third repeat unit opens during the reaction and bonds (e.g., covalently bonds) with the amine-containing polymer to form a structure represented by Formula IV. The fourth repeat unit represented by Formula IV in the first polymer can be understood to include a residue of a maleic anhydride-based polymer and a residue of an amine-containing polymer. Alternatively, the fourth repeat unit represented by Formula IV in the first polymer can be understood as a structure in which a residue of a maleic anhydride-based polymer is bonded to a residue of an amine-containing polymer. The term "residue of a maleic anhydride-based polymer" refers to a structure derived from a maleic anhydride-based polymer. The term "residue of an amine-containing polymer" refers to a structure derived from an amine-containing polymer. At least one of R1 and R2 of the fourth repeat unit in the first polymer can be derived from an amine-containing polymer. The reaction of the maleic anhydride-based polymer with the amine-containing polymer can include a grafting reaction.

[0048] In embodiments, the amine-containing polymer may include or be polyethyleneimine, and the polyethyleneimine may be branched or linear polyethyleneimine. At least one of R1 and R2 of the fourth repeat unit in the first polymer may be derived from polyethyleneimine. The branched polyethyleneimine may include a structure represented by the following chemical formula C-1. The linear polyethyleneimine may include a structure represented by the following chemical formula C-2.

[0049] [Chemical formula C-1] JPEG2026012049000015.jpg6071

[0050] [Chemical formula C-2] JPEG2026012049000016.jpg2554

[0051] Formula C-1 shows only a partial structure of branched polyethyleneimine, and the dotted lines indicate that the above structure can be expanded in a similar manner to form a macromolecule. In Formula C-2, x is an integer greater than 0.

[0052] In an embodiment, a method for manufacturing a lens 100 having a hydrophilic layer 20 includes the following steps: A lens body 10 manufactured by any suitable method is sequentially immersed in a first treatment solution containing an amine-containing polymer and a second treatment solution containing a maleic anhydride-based polymer; the amine-containing polymer and maleic anhydride-based polymer described above can be used. The maleic anhydride-based polymer can react with the amine-containing polymer to form a first polymer, and a hydrophilic layer 20 containing the first polymer can be formed on the outer surface S of the lens body 10 and / or on the interior of the lens body 10. In an embodiment, the first treatment solution and the second treatment solution can further contain methanol, ethanol, propanol, isopropanol, or acetone and / or deionized water. The immersion time of the lens in the first treatment solution and the immersion time of the lens in the second treatment solution are 30 seconds to 240 minutes. The temperature of the first treatment solution and the second treatment solution are 20°C to 60°C.

[0053] The weight-average molecular weight of the amine-containing polymer is in the range of 1,000 to 1,000,000, or 1,500 to 850,000, or 2,000 to 750,000. If the weight-average molecular weight of the amine-containing polymer is too low, the lens will exhibit reduced resistance to lipid adsorption. If the weight-average molecular weight of the amine-containing polymer is too high, the entanglement between the amine-containing polymer and the lens body will be affected, and the bonding performance between the amine-containing polymer and the maleic anhydride-based polymer will also be reduced, affecting the hydrophilicity of the lens and the lens's resistance to lipid adsorption.

[0054] The amine-containing polymer is present in the first treatment solution in an amount of 10 ppm to 20,000 ppm or 100 ppm to 15,000 ppm, based on the total weight of the first treatment solution. If the amount of amine-containing polymer is too low, the lens immersion time must be longer. If the amount of amine-containing polymer is too high, the lens will become white.

[0055] The weight-average molecular weight of the maleic anhydride-based polymer is in the range of 5,000 to 1,500,000, for example, 5,000 to 1,000,000 or 5,000 to 500,000. If the weight-average molecular weight of the maleic anhydride-based polymer is too high or too low, the bonding performance between the amine-containing polymer and the maleic anhydride-based polymer will be affected, affecting the properties of the lens.

[0056] The maleic anhydride-based polymer is present in the second processing solution in an amount of 10 ppm to 25,000 ppm, or 100 ppm to 20,000 ppm, based on the total weight of the second processing solution. If the amount of maleic anhydride-based polymer is too low, the lens immersion time must be longer.

[0057] In an embodiment, the method for manufacturing a lens having a hydrophilic layer further includes the following steps: After the lens has been treated with the second treatment solution, the lens having the hydrophilic layer is removed from the second treatment solution and stored in a buffer solution, and then the lens is subjected to a sterilization and packaging process. For example, the buffer solution may be phosphate buffered saline. Sterilization is performed at 110°C to 135°C for 3 to 120 minutes.

[0058] Referring to FIG. 3, FIG. 3 shows a schematic diagram of a lens 200 according to another embodiment of the present disclosure. The difference between the lens 200 and the lens 100 shown in FIG. 2 is that the lens 200 includes a base layer 30 formed between the lens body 10 and the hydrophilic layer 20. The base layer 30 is formed on at least a portion of the outer surface S of the lens body 10. The base layer 30 is formed on at least a portion of the front surface 11 of the lens body 10 and / or at least a portion of the back surface 12 of the lens body 10. In FIG. 3, the base layer 30 is illustrated as covering the front surface 11, back surface 12, and edge 13 of the lens body 10, but the present disclosure is not limited thereto. The hydrophilic layer 20 is formed on at least a portion of the surface of the base layer 30. The base layer 30 may be optically transparent. The base layer 30 includes a second polymer containing a carboxyl group. The second polymer of the base layer 30 can be selected from the group consisting of poly(acrylic acid) (PPA), polymethacrylate (PMA), poly(methyl methacrylate) (PMMA), and poly(methacrylic acid) (PMAA). The hydrophilic layer 20 of the lens 200 is not formed inside the lens body 10. In the hydrophilic layer 20 of the lens 200, the substituents R1 and R2 of the fourth repeat unit of the first polymer do not need to extend inside the lens body 10 or intertwine with the material of the lens body 10.

[0059] In the hydrophilic layer 20 of the lens 200, the amount of at least one of R1 and R2 of the fourth repeat unit in the first polymer decreases in a direction away from the outer surface of the lens body 10, and the amount of the first repeat unit and / or the second repeat unit increases in a direction away from the outer surface of the lens body 10. In the hydrophilic layer 20 of the lens 200, on the surface of the hydrophilic layer 20 facing the lens body 10, the amount of the fourth repeat unit in the first polymer is greater than the amount of the first repeat unit and / or the second repeat unit in the first polymer. In the hydrophilic layer 20 of the lens 200, on the surface of the hydrophilic layer 20 facing away from the lens body 10, the amount of the fourth repeat unit in the first polymer is less than the amount of the first repeat unit and / or the second repeat unit in the first polymer.

[0060] The method for manufacturing the lens 200 differs from the method for manufacturing the lens 100 in that the method for manufacturing the lens 200 further includes a step of immersing the lens body 10 in a third treatment solution containing a second polymer before immersing the lens body 10 in the first treatment solution. The second polymer is present in the third treatment solution in an amount of 10 ppm to 25,000 ppm or 100 ppm to 10,000 ppm, based on the total weight of the third treatment solution. If the amount of the second polymer is too small, the lens has low resistance to lipid adsorption. In an embodiment, the immersion 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.

[0061] <Applications of maleic anhydride-based polymers>

[0062] In embodiments, the maleic anhydride-based polymer can be used to prepare a composition that can be used to manufacture a hydrophilic lens. The lens composition includes a maleic anhydride-based polymer and a polymerizable monomer. The amount of maleic anhydride-based polymer can range from 0.05 wt % to 1 wt %, for example, 0.1 wt %, based on the total weight of the composition.

[0063] The polymerizable monomer may include a monomer containing an alkenyl group or a hydrophilic monomer containing an alkenyl group. The polymerizable monomer may include at least one of a hydrophilic monomer and a siloxane monomer. The siloxane monomer may include one or more different siloxane monomers. For example, the siloxane monomer may include at least one of a siloxane monomer containing a single methacryloyl group, a siloxane monomer containing two methacryloyl groups, and a siloxane monomer containing three or more methacryloyl groups. The polymerizable monomer may be at least one selected from the group consisting of a hydrophilic monomer and a siloxane monomer. In an embodiment, the siloxane monomer includes a siloxane monomer containing a single methacryloyl group and a siloxane monomer containing two methacryloyl groups.

[0064] <Hydrophilic monomer>

[0065] The hydrophilic monomer may be one or more molecules selected from the group consisting of 2-hydroxyethyl methacrylate (HEMA), methyl methacrylate (MMA), methacrylic acid (MAA), N-vinylpyrrolidone (NVP), N,N-dimethylacrylamide (DMA), 4-acryloylmorpholine (AcMO), 2-hydroxyethylacrylamide (HEAA), glycidyl methacrylate (GMA), glycerol monomethacrylate (GMMA), acrylic acid (AA), N,N-di(methyl methacrylamide) (DMA), hexafluoroisopropyl methacrylate (HFMA), N-vinyl-N-methylacetamide, glycine vinyl carbonate, 2-methacryloyloxyethyl phosphorylcholine, and 2-hydroxybutyl methacrylate.

[0066] <Siloxane monomer>

[0067] A methacryloyl group can be represented as CH2=C(CH3)CO-. Alternatively, a methacryloyl group can be represented as: It can be represented as JPEG2026012049000017.jpg2529.

[0068] The siloxane monomer containing a single methacryloyl group can be one or more molecules selected from the group consisting of the following formulas 1A-1H:

[0069] [Chemical formula 1A] JPEG2026012049000018.jpg3478

[0070] [Chemical formula 1B] JPEG2026012049000019.jpg26106

[0071] In chemical formula 1B, aa=4-80.

[0072] [Chemical formula 1C] JPEG2026012049000020.jpg35146

[0073] In Formula 1C, bb = 4 to 80, and cc = 3 to 40.

[0074] [Chemical formula 1D] JPEG2026012049000021.jpg5381

[0075] In formula 1D, dd = 2-40, and ee = 2-40.

[0076] [Chemical formula 1E] JPEG2026012049000022.jpg53103

[0077] In Formula 1E, ff=2-40, and gg=2-40.

[0078] [Chemical formula 1F] JPEG2026012049000023.jpg18132

[0079] In chemical formula 1F, hh = 4 to 80.

[0080] [Chemical formula 1G] JPEG2026012049000024.jpg18119

[0081] In formula 1G, ii = 4-80.

[0082] [Chemical formula 1H] JPEG2026012049000025.jpg3275

[0083] In Formula 1H, TMS is an abbreviation for trimethylsiloxy.

[0084] The siloxane monomer containing two methacryloyl groups may be one or more molecules selected from the group consisting of the following formulas 2A-2C:

[0085] [Chemical formula 2A] JPEG2026012049000026.jpg43147

[0086] In Formula 2A, jj = 4-80, kk = 1-10, and rr = 1-10.

[0087] [Chemical formula 2B] JPEG2026012049000027.jpg21125

[0088] In chemical formula 2B, ss = 4 to 80.

[0089] [Chemical formula 2C] JPEG2026012049000028.jpg30133

[0090] In chemical formula 2C, tt = 4 to 80.

[0091] In embodiments, based on the total weight of the siloxane monomers, the amount of siloxane monomers containing a single methacryloyl group may range from 50 wt % to 91 wt %, and the amount of siloxane monomers containing two methacryloyl groups may range from 9 wt % to 50 wt %.

[0092] In an embodiment, the lens composition may further contain an ultraviolet absorber, an initiator, and / or a blue light absorber. The ultraviolet absorber may be selected from ultraviolet absorbers known in the art that are applicable to contact lens materials. The amount of the ultraviolet absorber may be in the range of 0.01 wt% to 5 wt% based on the total weight of the lens composition. The initiator may be a thermal initiator or a photoinitiator. The thermal initiator and photoinitiator may be selected from initiators known in the art that can be used in polymerization reactions. The amount of the initiator may be in the range of 0.45 wt% to 0.75 wt% based on the total weight of the lens composition. The type and amount of the blue light absorber can be selected by a person of ordinary skill in the relevant art according to actual needs. For example, the blue light absorber may be Reactive Yellow 15. In an embodiment, the amount of the blue light absorber may be in the range of 0.1 wt% to 5 wt% based on the total weight of the lens composition.

[0093] The above components can be mixed in specific ratios to form a lens composition. In embodiments, the lens composition can be placed into a contact lens mold, and the components in the composition undergo a curing reaction (thermal curing or photocuring) through heating or light irradiation to form the lens. The heating temperature can be between about 30°C and about 150°C, and the heating time can be between about 1 hour and 12 hours. A hydration process and / or a sterilization process can be performed after the curing reaction. The hydration process can include immersing the lens in alcohol and pure water, followed by placing the lens in a buffer solution to allow it to equilibrate.

[0094] <Applications of maleic anhydride-based polymers>

[0095] In embodiments, the maleic anhydride-based polymer can be used to prepare a hydrophilic treatment agent, which can be applied to lenses. For example, the lens treatment agent can be a lens packing solution (lens transport solution), a lens cleaning solution, a lens care solution, or a lens disinfecting solution. A lens packing solution refers to a solution stored in a packaging container together with a lens. Lenses are typically sold in a packaging container that contains the packing solution. The lens packing solution can be a buffer solution. When the lens comes into contact with the treatment agent, the treatment agent can either penetrate into the lens or adhere to its surface, improving the moisturizing and comfort of the lens.

[0096] The lens treatment agent includes at least a buffer solution and a maleic anhydride-based polymer. The treatment agent may include 0.05 wt% to 5 wt%, for example 0.1 wt% to 2 wt%, of the maleic anhydride-based polymer based on the total weight of the treatment agent. The buffer solution may include one or more of boric acid or a salt thereof, trometamol, 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.

[0097] In embodiments, the treatment agent may further include a humectant, a vitamin, an osmotic pressure adjuster, a surfactant, a cooling agent, or any combination thereof. The humectant may be one or more selected from the group consisting of methylcellulose (MC), hydroxypropylmethylcellulose (HPMC), hydroxyethylcellulose, carboxymethylcellulose (CMC), hyaluronic acid (HA), a salt of hyaluronic acid (hyaluronate), alginic acid, a salt of alginic acid, a polymer containing a phosphorylcholine group, polyvinylpyrrolidone (PVP), and glucan. For example, the polymer containing a phosphorylcholine group may be poly[2-methacryloyloxyethylphosphorylcholine] (poly-MPC), a copolymer of 2-methacryloyloxyethylphosphorylcholine (MPC) and a methacrylic acid ester, or a combination thereof. The amount of the humectant may range from 0.01 wt% to 1 wt% based on the total weight of the treatment agent.

[0098] The vitamin may 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 may be one or more selected from the group consisting of vitamin B1, vitamin B2, vitamin B3, vitamin B6, and vitamin B12. The amount of the vitamin may be in the range of 0.001 wt% to 1 wt%, for example, 0.001 wt% to 0.5 wt%, based on the total weight of the treatment agent. The osmolality adjuster may be one or more selected from the group consisting of sodium chloride, potassium chloride, calcium chloride, zinc chloride, magnesium chloride, and dextrose. The amount of the osmolality adjuster may be in the range of 0.01 wt% to 2.5 wt% based on the total weight of the treatment agent. The osmolality adjuster can adjust the osmolality of the treatment agent so that the osmolality of the treatment agent is close to that of normal tears. The surfactant may be one or more selected from the group consisting of nonionic surfactants, cationic surfactants, and zwitterionic surfactants. The type and amount of surfactant can be selected by a person of ordinary skill in the relevant technical field according to actual needs. For example, the amount of surfactant can be in the range of 0.0001 wt% to 5.0 wt% based on the total weight of the treatment agent. The type and amount of coolant can be selected by a person of ordinary skill in the relevant technical field according to actual needs. For example, the amount of coolant can be in the range of 0.0001 wt% to 1.0 wt% based on the total weight of the treatment agent.

[0099] In an embodiment, the treatment agent may further include a pharmaceutically active ingredient. For example, the pharmaceutically active ingredient may be a vasoconstrictor, an anti-inflammatory agent, an astringent, an anti-allergic agent, an antibacterial agent, or any combination thereof. The amount of the pharmaceutically active ingredient may be in the range of 0.001 wt% to 5.0 wt% based on the total weight of the treatment agent.

[0100] In an embodiment, the treatment agent includes a maleic anhydride-based polymer, vitamin B, a polymer containing phosphorylcholine groups, and deionized water. The treatment agent containing both vitamin B and phosphorylcholine groups can enhance the moisturizing and comfort of the lens.

[0101] The above components can be added to deionized water in a specific ratio and mixed uniformly with the deionized water to form a treatment agent.

[0102] To make the above-mentioned objects, features, and advantages of the present disclosure more apparent, the present disclosure will be described in more detail with reference to examples. [Example]

[0103] Maleic anhydride-based polymer

[0104] Maleic anhydride-based polymers (hereinafter referred to as "products") are produced by the above-described manufacturing method according to the compositions and ratios shown in Table 1 below. In the examples and comparative examples in Table 1, maleic anhydride is used as the maleic anhydride-containing compound. The amount of the third repeat unit represents the ratio of the weight of the third repeat unit in the product to the total weight of the product. The product is added to a determined volume of water at a ratio of 1%. The solubility is evaluated visually, and the amount of the third repeat unit is determined by titration. The symbol "○" indicates that the product is soluble in water and forms a clear solution. In contrast, the symbol "×" indicates incomplete dissolution, resulting in a cloudy white solution.

[0105] [Table 1]

[0106] In Comparative Example 1, maleic anhydride was used to form polymaleic anhydride (i.e., a polymer not modified with polyethylene glycol dimethacrylate) and test its water solubility. The test results showed that polymaleic anhydride exhibited poor water solubility and resulted in the formation of a precipitate. In Comparative Example 2, the amount of maleic anhydride-containing compound was too high, resulting in low water solubility of the resulting product, leading to the formation of a precipitate. Due to the precipitate, the amount of the third repeating unit could not be determined by titration. All of the maleic anhydride-based polymers in Examples 1 to 5 dissolved in water without precipitation or turbidity, indicating that the present disclosure can effectively improve solubility by modifying them with polyethylene glycol dimethacrylate at a specific ratio. Furthermore, modification with polyethylene glycol dimethacrylate does not open the ring structure of the maleic anhydride group, thus maintaining the reactivity of the maleic anhydride group. The ring-opened maleic anhydride group is difficult to combine with other materials (such as amine-containing polymers) in the subsequent hydrophilic layer manufacturing process, and therefore, a stable hydrophilic layer cannot be formed.

[0107] In addition to visual observation, a dynamic light scattering (DSL) device can be used to measure the transmittance (%) of the aqueous solution of the product, which is prepared by adding the product to a certain amount of water at a concentration of 1%. The test results show that the aqueous solution of the product of Example 1 has a transmittance of 86% or more, while the solution of the product of Comparative Example 2 has a transmittance of less than 86%. This indicates that the product of Example 1 has better water solubility than the product of Comparative Example 2.

[0108] <Lens with hydrophilic layer>

[0109] The maleic anhydride-based polymers of Examples 1 to 5 were prepared by the above-described manufacturing method according to the compositions and ratios shown in Table 1. The maleic anhydride-based polymers of Examples 1 to 5 were then used in the above-described manufacturing method for lenses having hydrophilic layers to form lenses having hydrophilic layers of Examples 1A to 5B. The compositions used in the manufacturing method for lenses having hydrophilic layers are shown in Table 2 below. Examples 1A and 1B used the maleic anhydride-based polymer of Example 1, and the lens of Example 1B further included a base layer. Examples 2A and 2B used the maleic anhydride-based polymer of Example 2, and the lens of Example 2B further included a base layer. Examples 3A and 3B used the maleic anhydride-based polymer of Example 3, and the lens of Example 3B further included a base layer. Examples 4A and 4B used the maleic anhydride-based polymer of Example 4, and the lens of Example 4B further included a base layer. Examples 5A and 5B used the maleic anhydride-based polymer of Example 5, and the lens of Example 5B further included a base layer. Comparative Example 3 is a lens that does not include a hydrophilic layer or a base layer (untreated lens). The examples and comparative examples shown in Table 2 use silicone hydrogel contact lenses that have the same composition as the lens body.

[0110] [Table 2]

[0111] The manufacturing methods and conditions used in the examples and comparative examples shown in Table 2 are as follows: An amine-containing polymer is dissolved in ethanol and deionized water, and these compounds are mixed together to form a first treatment solution. A maleic anhydride-based polymer is dissolved in deionized water, and these compounds are mixed together to form a second treatment solution. A second polymer is dissolved in ethanol and deionized water, and these compounds are mixed together to form a third treatment solution. A lens body is immersed in the first treatment solution for 60 to 120 minutes. The lens body is removed from the first treatment solution and then immersed in the second treatment solution for 60 to 120 minutes. A lens structure including a lens body and a hydrophilic layer is removed from the second treatment solution and then stored in a buffer solution. Sterilization and packaging are performed on the lens structure including a lens body and a hydrophilic layer. Sterilization is performed at 125°C for 50 minutes. Examples 1B, 2B, 3B, 4B, and 5B further include immersing the lens body in a third treatment solution for 60 to 120 minutes before immersing the lens body in the first treatment solution.

[0112] The water contact angles were evaluated for the lenses of Examples 1A to 5B and Comparative Example 3. The results are shown in Table 2 above.

[0113] <Experimental Example 1: Evaluation of water contact angle>

[0114] The lens is placed on a clean nonwoven fabric. The lens is pressed against the clean nonwoven fabric for 10 seconds to remove moisture from the lens surface. Next, a contact angle meter (DSA25, KRUSS) is used to analyze the contact angle (water contact angle) between the surface of the water droplet and the lens surface. The larger the water contact angle, the more hydrophobic the lens surface. The smaller the water contact angle, the more hydrophilic the lens surface.

[0115] The 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 surfaces of the lenses of the present disclosure exhibited higher hydrophilicity. The contact angles of the lenses of Examples 2B, 3B, and 4B were 60° or less, indicating that the base layer can further improve the hydrophilicity of the lenses. Furthermore, staining tests using Sudan staining solution were performed on the lenses of Examples 1B, 2B, 3B, 4B, and 5B. The test results showed that the lenses of Examples 1B, 2B, 3B, 4B, and 5B were either not stained or only slightly stained, indicating that the base layer can increase the lens's resistance to lipid adsorption. As shown in Table 2, the surfaces of the lenses according to the present disclosure have high hydrophilicity and strong resistance to lipid adsorption, thereby effectively improving the wearer's comfort and helping to reduce eye dryness, infection, and damage.

[0116] <Lens treatment agent>

[0117] A lens treatment agent is prepared by mixing the components shown in Table 3 in the ratios shown in the table and stirring the mixture until no undissolved material remains in the solution. In Table 3, the maleic anhydride-based polymer is the maleic anhydride-based polymer of Example 1, and deionized water is used as the solvent. One milliliter of the lens treatment agent is placed in a packaging container, the lens is immersed in the treatment agent in the packaging container, aluminum foil is attached to the packaging container by heat sealing, and then sterilization is performed. The sterilization conditions are as described above. The lenses of Examples 6 to 10 and Comparative Example 4 are evaluated for water contact angle. The results are shown in Table 3. The water contact angle evaluation is performed as described above. The treatment agents of Examples 6 to 10 can be used as lens packaging solutions.

[0118] [Table 3]

[0119] As shown in Table 3, the water contact angles of Examples 6 to 10 were all smaller than the water contact angle of Comparative Example 4, which means that storing lenses in the treatment agent of the present disclosure can increase the hydrophilicity of the lens surface and improve the wear comfort for the user.

[0120] <Lens composition>

[0121] In Example 11, the lens composition contains 0.1 wt% (based on the total weight of the composition) of a maleic anhydride-based polymer, a hydrophilic monomer, and a siloxane monomer. In Comparative Example 5, the lens composition contains only a hydrophilic monomer and a siloxane monomer, and does not contain a maleic anhydride-based polymer. Example 11 and Comparative Example 5 use the same hydrophilic monomer and siloxane monomer, and the manufacturing method for preparing the lens composition described above is used. The lens compositions of Example 11 and Comparative Example 5 are placed into contact lens molds, and lenses are obtained through the manufacturing method described above. Water contact angle evaluation is performed on the lenses of Example 11 and Comparative Example 5, as described above. The water contact angle of Example 11 is 82°, and the water contact angle of Comparative Example 5 is 85°, which means that the use of the maleic anhydride-based polymer of the present disclosure in the lens composition can improve the hydrophilicity of the lens surface.

[0122] Therefore, the maleic anhydride-based polymer of the present disclosure can effectively increase the solubility of the maleic anhydride-based polymer while maintaining the reactivity of the maleic anhydride group. The lenses, lens treatment agents, and lens compositions of the present disclosure can effectively increase hydrophilicity and resistance to lipid adsorption, improve wear comfort for users, and solve the problem of low transparency caused by lipids adsorbed on the lens surface. Moreover, the present disclosure has the advantages of a simple manufacturing process, low cost, and high yield.

[0123] While this disclosure has been described by way of example and in terms of exemplary embodiments, it is to be understood that the disclosure is not limited thereto. On the contrary, it is intended to cover various modifications and similar arrangements and procedures. The scope of the appended claims, therefore, should be accorded the broadest interpretation so as to encompass all such modifications and similar arrangements and procedures.

Claims

1. one or more first repeat units represented by the following formula I: one or more second repeat units represented by Formula II: one or more third repeat units represented by Formula III: [Chemical formula I] [Chemical formula II] [Chemical formula III] (However, in Chemical Formula II, R a is H or C 1 -C 3 is an alkyl group, and R b is H or C 1 -C 3 an alkyl group, or the one or more first repeat units, or the one or more second repeat units, or the one or more third repeat units. Maleic anhydride-based polymers, including

2. 10. The maleic anhydride-based polymer of claim 1, wherein the amount of the one or more third repeat units ranges from 0.5 wt % to 9 wt %, based on the total weight of the maleic anhydride-based polymer.

3. 10. The maleic anhydride-based polymer of claim 1, wherein the value of the molar ratio of the one or more second repeat units to the one or more third repeat units is in the range of 0.5 to 50.

4. 2. The maleic anhydride-based polymer of claim 1, wherein the maleic anhydride-based polymer comprises z first repeat units, m second repeat units, and p third repeat units, wherein z is in the range of 4 to 50, m is in the range of 10 to 50, and p is in the range of 1 to 20.

5. 2. The maleic anhydride-based polymer of claim 1 , wherein the one or more first repeat units are attached to the one or more second repeat units, and the one or more third repeat units are attached to the one or more second repeat units.

6. The maleic anhydride-based polymer has the following chemical formula A [Chemical formula A] (wherein z is in the range of 4 to 50, m is in the range of 10 to 50, and p is in the range of 1 to 20).

2. The maleic anhydride-based polymer of claim 1, represented by:

7. A lens having a hydrophilic layer, The lens body and the hydrophilic layer on at least a portion of the outer surface of the lens body; The hydrophilic layer comprises a first polymer, the first polymer comprising: one or more first repeat units represented by the following formula I: one or more second repeat units represented by Formula II: one or more fourth repeat units represented by Formula IV: [Chemical formula I] [Chemical formula II] [Chemical formula IV] (However, in Chemical Formula IV, R 1 is H or a substituent containing at least one of a primary amine group, a secondary amine group, and a tertiary amine group; R 2 is a substituent comprising at least one of a primary amine group, a secondary amine group, and a tertiary amine group; In Formula II, R a is H or C 1 -C 3 is an alkyl group, and R b is H or C 1 -C 3 an alkyl group, or the one or more first repeat units, or the one or more second repeat units, or the one or more fourth repeat units. Including the lens.

8. 8. The lens having a hydrophilic layer according to claim 7, wherein a molar ratio of the one or more second repeating units to the one or more fourth repeating units is in the range of 0.5 to 50.

9. 8. The lens having a hydrophilic layer according to claim 7, wherein the first polymer comprises z first repeat units and m second repeat units, where z is in the range of 4 to 50 and m is in the range of 10 to 50.

10. the lens having the hydrophilic layer further includes a base layer formed between the lens body and the hydrophilic layer, the base layer including a second polymer including a carboxyl group; A lens having the hydrophilic layer according to claim 7.

11. The first polymer is represented by the following formula B [Chemical formula B] (wherein z is in the range of 4 to 50, m is in the range of 10 to 50, and q is in the range of 1 to 20).

8. A lens having a hydrophilic layer according to claim 7, wherein the hydrophilic layer is represented by the formula:

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

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

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

15. The maleic anhydride-based polymer of claim 1; a polymerizable monomer; A lens composition comprising:

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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