Maleic anhydride-based polymer, lens with hydrophilic layer, processing agent for lens, and composition for lens

Abstract

Provided are a maleic anhydride-based polymer, a lens having a hydrophilic coating, a treatment agent for the lens, and a composition for the lens. The maleic anhydride-based polymer comprises one or more first repeating units represented by Formula I, one or more second repeating units represented by Formula II, and one or more third repeating units represented by Formula III. In Formula II, Ra is H or a C1-C3 alkyl group, and Rb is H or a C1-C3 alkyl group, or a first repeating unit, a second repeating unit, or a third repeating unit.

Description

Technical Field

[0001] This invention relates to polymers based on maleic anhydride, lenses having a hydrophilic coating, treatment agents for lenses, and compositions for lenses. Prior Technology

[0002] Maleic anhydride compounds are common materials for improving hydrophilicity, and they can be used to form hydrophilic coatings, contact lenses, and as treatment agents for contact lenses. However, the poor solubility of maleic anhydride can lead to the formation of suspended particles in the solution, which can be clearly seen as a cloudy white color. This increases the difficulty of the manufacturing process, reduces the reactivity of maleic anhydride compounds with other materials, and also results in poor quality of the finished product. Summary of the Invention

[0003] This invention relates to a polymer based on maleic anhydride and a lens with a hydrophilic coating. The maleic anhydride-containing compound is modified to improve its solubility, thereby improving the hydrophilicity and stability of the hydrophilic coating and enhancing user comfort. Simultaneously, the lens exhibits excellent anti-oil adsorption properties. This invention also relates to a lens treatment agent and a lens composition comprising a polymer based on maleic anhydride, thereby improving the lens's hydrophilicity and enhancing user comfort.

[0004] According to one embodiment of the present invention, a polymer based on maleic anhydride is proposed. The polymer based on maleic anhydride comprises one or more first repeating units represented by Formula I, one or more second repeating units represented by Formula II, and one or more third repeating units represented by Formula III. In Formula II, Ra is H or a C1-C3 alkyl group, and Rb is H or a C1-C3 alkyl group, or a first repeating unit, a second repeating unit, or a third repeating unit.

[0005] [Formula I]

[0006] [Formula II]

[0007] [Formula III]

[0008] According to one embodiment of the present invention, a lens having a hydrophilic coating is provided. The lens having the hydrophilic coating comprises a lens body and a hydrophilic coating. The hydrophilic coating is at least partially formed on the outer surface of the lens body. The hydrophilic coating comprises a first polymer. The first polymer comprises one or more first repeating units represented by Formula I, one or more second repeating units represented by Formula II, and one or more fourth repeating units represented by Formula IV. In Formula IV, R1 is H or a substituent comprising at least one of a primary amino group, a secondary amino group, and a tertiary amino group. In Formula IV, R2 is a substituent comprising at least one of a primary amino group, a secondary amino group, and a tertiary amino group. In Formula II, Ra is H or a C1-C3 alkyl group, and Rb is H or a C1-C3 alkyl group, or a first repeating unit, a second repeating unit, or a fourth repeating unit.

[0009] [Formula I]

[0010] [Formula II]

[0011] [Form IV]

[0012] According to one embodiment of the present invention, a treatment agent for lenses is provided. The treatment agent comprises a buffer solution and a maleic anhydride-based polymer.

[0013] According to one embodiment of the present invention, a composition for a lens is provided. The composition comprises a maleic anhydride-based polymer and a polymerizable monomer.

[0014] To provide a better understanding of the above and other aspects of this disclosure, specific embodiments are described below in conjunction with the accompanying drawings: Simple Explanation of the Diagram

[0015] Figure 1 is a schematic diagram illustrating a lens body according to one embodiment of the present invention; Figure 2 is a schematic diagram illustrating a lens according to one embodiment of the present invention; and Figure 3 is a schematic diagram illustrating a lens according to another embodiment of the present invention. Implementation

[0016] <Polymers Based on Maleic Anhydride and Their Manufacturing Methods>

[0017] 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. Wherein z, m, and p are integers greater than or equal to 1 or non-integers. In Formula I, the line segment extending from inside the parentheses to outside the parentheses represents a bond to another repeating unit or other functional group; the other repeating unit may be the first repeating unit, the second repeating unit, or the third repeating unit. In Formula II, Ra is H or a C1-C3 alkyl group, and Rb is H or a C1-C3 alkyl group or another repeating unit; the other repeating unit may be the first repeating unit, the second repeating unit, or the third repeating unit. In Formula III, the line segment extending from inside the parentheses to outside the parentheses represents a bond to another repeating unit or other functional group; the other repeating unit may be the first repeating unit, the second repeating unit, or the third repeating unit. In polymers based on maleic anhydride, 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.

[0018] [Formula I]

[0019] [Formula II]

[0020] [Formula III]

[0021] 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 another embodiment, the mole ratio of the second repeating unit to the third repeating unit in the maleic anhydride-based polymer may be 2.3, 2.5, 3, 8, or 21.

[0022] 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. Based on the total weight of the maleic anhydride-based polymer described above, the content of the third repeating unit can be from 0.5 wt% (weight percentage concentration) to 9 wt%, for example, from 0.8 wt% to 8 wt%, or from 2.5 wt% to 7.4 wt%. If the content of the third repeating unit is too low, the reactivity of the maleic anhydride-based polymer when used to form a hydrophilic coating is poor. If the content of the third repeating unit is too high, the solubility in water is poor and precipitation may even occur.

[0023] The weight-average molecular weight (Mw) of polymers based on maleic anhydride can range from 5,000 to 1,500,000, for example, between 5,000 and 1,000,000 or between 5,000 and 500,000. The infrared spectra of polymers based on maleic anhydride are at 1780... It has at least one absorption peak nearby, at 1728 There is at least one absorption peak nearby.

[0024] In a polymer based on maleic anhydride, 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 a polymer based on maleic anhydride, 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. The 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 the 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, a polymer based on maleic anhydride can be represented by formula A, where the ranges of z, m, and p in formula A are as described above.

[0025] [Formula A]

[0026] The following examples illustrate a method for manufacturing polymers based on maleic anhydride, but the invention is not limited thereto, and polymers based on maleic anhydride can also be formed by other manufacturing methods.

[0027] Maleic anhydride-based polymers can be formed by reacting a maleic anhydride-containing compound with polyethylene glycol dimethacrylate (PEGMA). In one embodiment, a method for manufacturing a maleic anhydride-based polymer may include the following steps: placing a maleic anhydride-containing compound, polyethylene glycol dimethacrylate, and an initiator 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 a maleic anhydride-based polymer. The initiator may include or may be a photoinitiator or a thermal initiator.

[0028] The type and amount of photoinitiator and thermal initiator added can be selected by those skilled in the art according to actual needs. Solvents can be methanol, ethanol, acetone, dimethyl sulfoxide, dimethylformamide, tetrahydrofuran, N-methyl-2-pyrrolidone, or dimethylacetamide. Compounds containing maleic anhydride may include or may be maleic anhydride.

[0029] Methods for manufacturing polymers based on maleic anhydride may further include steps such as heating or irradiating the raw material solution with light, and / or concentrating under reduced pressure, and / or washing the product with a cleaning solution. Methods for manufacturing polymers based on maleic anhydride can be understood as modifying maleic anhydride-containing compounds using polyethylene methacrylate. Methods for manufacturing polymers based on maleic anhydride may include free radical polymerization reactions.

[0030] <Applications of Polymers Based on Maleic Anhydride>

[0031] The maleic anhydride-based polymers of this invention can be applied to various products to enhance their hydrophilicity, such as hydrophilic coatings, hydrophilic lenses, and hydrophilic treatment agents. In one embodiment, the maleic anhydride-based polymer can be used to form a hydrophilic coating in a lens. The application of one such maleic anhydride-based polymer will be described below with reference to Figures 1 and 2.

[0032] Please refer to Figures 1 and 2. Figure 1 is a schematic diagram illustrating a lens body 10 according to one embodiment, and Figure 2 is a schematic diagram illustrating a lens 100 according to one embodiment. The lens 100 includes a lens body 10 and a hydrophilic coating 20. The lens body 10 can be a rigid contact lens or a soft contact lens. The lens body 10 can be a hydrogel contact lens or a silicone hydrogel contact lens. In one embodiment, the lens body 10 is a silicone hydrogel contact lens, a tinted contact lens, a patterned contact lens, an anti-ultraviolet contact lens, an anti-blue light contact lens, an astigmatism contact lens, 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 includes a front surface 11, a rear surface 12, and an edge 13. The edge 13 connects the front surface 11 and the rear surface 12. The front surface 11 is opposite to the rear surface 12. The edge 13 of the lens body 10 can be circular, elliptical, or of any shape. The front surface 11 and the rear surface 12 may be curved surfaces. In Figure 1, the front surface 11 is depicted as a convex curved surface, and the rear surface 12 is depicted as a concave curved surface, but the invention is not limited thereto. When the lens body 10 is placed on the surface of a user's eye, the rear 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 coating 20 is at least partially formed on the outer surface S of the lens body 10. The hydrophilic coating 20 may be formed on at least a portion of the front surface 11 and / or at least a portion of the rear surface 12 of the lens body 10. The hydrophilic coating 20 may cover the outer surface S of the lens body 10. In Figure 2, the hydrophilic coating 20 is depicted covering the front surface 11, the rear surface 12, and the edge 13 of the lens body 10, but the invention is not limited thereto. The hydrophilic coating 20 may adhere to the outer surface S of the lens body 10. Alternatively, a portion of the hydrophilic coating 20 may adhere to the outer surface S of the lens body 10, while another portion of the hydrophilic coating 20 may be formed inside the lens body 10. This improves the adhesion between the hydrophilic coating 20 and the lens body 10, thereby enhancing the durability of the lens 100. There may be no chemical bond between the hydrophilic coating 20 and the lens body 10. The hydrophilic coating 20 may be optically transparent.

[0033] The hydrophilic coating 20 comprises a first polymer. The first polymer comprises z first repeating units represented by Formula I above, m second repeating units represented by Formula II above, and q fourth repeating units represented by Formula IV below. Wherein z and m range as described above, and q is an integer greater than or equal to 1 or a non-integer. In Formula IV, R1 is H or a substituent comprising at least one of a primary, secondary, and tertiary amino group. In Formula IV, R2 is a substituent comprising at least one of a primary, secondary, and tertiary amino group. In the first polymer, Ra in Formula II above is H or a C1-C3 alkyl group, and Rb is H or a C1-C3 alkyl group or another repeating unit, which may be a first repeating unit, a second repeating unit, or a fourth repeating unit. In Formula IV, the line segment extending from inside the parentheses 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 fourth repeating unit. In the first polymer, one or more first repeating units, one or more second repeating units, and one or more fourth repeating units may be randomly bonded to each other.

[0034] [Form IV]

[0035] In one embodiment, q is between 1 and 20, for example, between 5 and 15.

[0036] In one embodiment, at least one of R1 and R2 in Formula IV may include a structure represented by Formula IV-1 or Formula IV-2.

[0037] [Formula IV-1]

[0038] [Formula IV-2]

[0039] In Equation IV-1, *1 represents the N-bond with the fourth repeating unit; the dashed line indicates that the structure represented by Equation IV-1 can be extended into a larger structure with similar structures. In Equation IV-2, *2 represents the N-bond with the fourth repeating unit, and x is a positive integer.

[0040] In the first polymer, at least one first repeating unit may be bonded to a second repeating unit, and at least one fourth repeating unit may be bonded to a second repeating unit. In one embodiment, in the first polymer, a plurality of first repeating units may be bonded to each other to form a first chain structure, a plurality of second repeating units may be bonded to each other to form a second chain structure, and a plurality of fourth repeating units may be bonded to each other to form a fourth chain structure. The first repeating unit at the end of the first chain structure may be bonded to a second repeating unit in the second chain structure, and the fourth repeating unit at the end of the fourth chain structure may be bonded to a second repeating unit in the second chain structure. In one embodiment, the first polymer may be represented by the following formula B, wherein the ranges of z, m, and q in formula B are as described above, and the definitions of R1 and R2 in formula B are as described above. In one embodiment, the mole number ratio of the second repeating unit to the fourth repeating unit in the first polymer is between 0.5 and 50, for example, between 2 and 30. In one embodiment, the mole number ratio of the second repeating unit to the fourth repeating unit in the first polymer may be 2.3, 2.5, 3, 8, or 21.

[0041] [Formula B]

[0042] The hydrophilic coating 20 may have a non-covalent bond with the lens body 10. The hydrophilic coating 20 may adhere to the lens body 10 through a non-covalent bond between at least one of the R1 and R2 substituents in the fourth repeating unit of the first polymer and the lens body 10. At least one of the R1 and R2 substituents in the fourth repeating unit of the first polymer may adhere to the lens body 10 through intermolecular forces. At least one of the R1 and R2 substituents in the fourth repeating unit may penetrate 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, thereby improving the durability of the lens 100.

[0043] In one embodiment, in the hydrophilic coating 20, the content of 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 may 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).

[0044] In one 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 a 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.

[0045] 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 a third repeating unit represented by Formula III in the maleic anhydride-based polymer with the amine-containing polymer, wherein 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 the structure represented by Formula IV. The fourth repeating unit represented by Formula IV in the first polymer can also be understood as comprising residues of the maleic anhydride-based polymer and residues of the amine-containing polymer, or as residues of the maleic anhydride-based polymer bonded to residues of the amine-containing polymer. The term "residues of the maleic anhydride-based polymer" can refer to a structural portion derived from the maleic anhydride-based polymer. The term "residues of the amine-containing polymer" can refer to a structural portion derived from the amine-containing polymer. At least one of the R1 and R2 substituents of the fourth repeating unit in the first polymer can be derived from the amine-containing polymer. The reaction between the maleic anhydride-based polymer and the amine-containing polymer can include a grafting reaction.

[0046] In one embodiment, the amine-containing polymer may comprise or may be polyethyleneimine, which is branched polyethylenimine and / or linear polyethyleneimine; at least one of the R1 and R2 substituents of the fourth repeating unit in the first polymer may be derived from polyethyleneimine. Branched polyethyleneimine may comprise the structure represented by formula C-1. Linear polyethyleneimine may comprise the structure represented by formula C-2.

[0047] [Formula C-1]

[0048] [Formula C-2]

[0049] Equation C-1 shows only a partial structure of branched polyethyleneimine, and the dashed lines represent structures that can be extended to form polymers. In Equation C-2, x is a positive integer.

[0050] In one embodiment, a method for manufacturing a lens 100 having a hydrophilic coating 20 may include 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 the maleic anhydride-based polymer described above may be used. The maleic anhydride-based polymer and the amine-containing polymer can react to form a first polymer, and the hydrophilic coating 20 containing 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 and second treatment solutions may 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 from 30 seconds to 240 minutes, and the temperature of the first and second treatment solutions is 20°C. Up to 60

[0051] The weight-average molecular weight of the amine-containing polymer can range from 1,000 to 1,000,000, or from 1,500 to 850,000, or from 2,000 to 750,000. If the weight-average molecular weight of the amine-containing polymer is too low, it will reduce the lens's anti-oil adsorption effect. If the weight-average molecular weight of the amine-containing polymer is too high, it will affect its entanglement with the lens body and reduce its bonding with maleic anhydride-based polymers, thereby affecting the lens's hydrophilicity and anti-oil adsorption.

[0052] The concentration of the amine-containing polymer in the first treatment solution relative to the total weight of the first treatment solution can be between 10 ppm and 20,000 ppm, or between 100 ppm and 15,000 ppm. If the concentration of the amine-containing polymer is too low, the lens will require a longer soaking time. If the concentration of the amine-containing polymer is too high, the lens will exhibit whitening.

[0053] The weight-average molecular weight of maleic anhydride-based polymers 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. If the weight-average molecular weight of the maleic anhydride-based polymer is too high or too low, it will affect the bonding effect between the maleic anhydride-based polymer and the amine-containing polymer, thus affecting the properties of the lens.

[0054] The concentration of the maleic anhydride-based polymer in the second treatment solution relative to the total weight of the second treatment solution can be between 10 ppm and 25,000 ppm, or between 100 ppm and 20,000 ppm. If the concentration of the maleic anhydride-based polymer is too low, the lens will require a longer soaking time.

[0055] In one embodiment, the method for manufacturing a lens 100 having a hydrophilic coating 20 may further include the following steps: After immersion in a second treatment solution, the lens with the hydrophilic coating is removed from the second treatment solution and placed in a buffer solution for a sealing and sterilization process. The buffer solution may be, for example, phosphate-buffered saline. The sterilization conditions are 110°C. Up to 135 The duration can range from 3 minutes to 120 minutes.

[0056] Please refer to Figure 3. Figure 3 is a schematic diagram illustrating a lens 200 according to another embodiment. The difference between lens 200 and lens 100 shown in Figure 2 is that lens 200 includes a base layer 30 formed between lens body 10 and hydrophilic coating 20. The base layer 30 is at least partially formed on the outer surface S of lens body 10. The base layer 30 may be formed on at least a portion of the front surface 11 and / or at least a portion of the rear surface 12 of lens body 10. In Figure 3, the base layer 30 is shown covering the front surface 11, rear surface 12, and edge 13 of lens body 10, but the invention is not limited thereto. The hydrophilic coating 20 is at least partially formed on the surface of the base layer 30. The base layer 30 may be optically transparent. The base layer 30 includes a second polymer having carboxyl groups. The second polymer of the base layer 30 may 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 of the lens 200, the R1 and R2 substituents of the fourth repeating unit of the first polymer cannot penetrate into the interior of the lens body 10 and become entangled with the lens material.

[0057] In the hydrophilic coating 20 of the lens 200, the content of 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 of the lens body 10, and 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 of the lens body 10. In the hydrophilic coating 20 of the lens 200, the content of the fourth repeating unit in the first polymer on the side of the hydrophilic coating 20 facing the lens body 10 is greater than the content of the first repeating unit and / or the second repeating unit. In the hydrophilic coating 20 of the lens 200, the content of the fourth repeating unit in the first polymer on the side of the hydrophilic coating 20 away from the lens body 10 is less than the content of the first repeating unit and / or the second repeating unit.

[0058] The difference between the manufacturing method of lens 200 and that of lens 100 lies in that the manufacturing method of lens 200 further includes immersing the lens body 10 in a third treatment solution containing a second polymer before immersing it in the first treatment solution. The content of the second polymer in the third treatment solution relative to the total weight of the third treatment solution can be between 10 ppm and 25,000 ppm, or between 100 ppm and 10,000 ppm. If the content of the second polymer is too low, the anti-lipid adsorption effect of the lens will be low. In one embodiment, the immersion time of the lens in the third treatment solution is between 30 seconds and 240 minutes. The temperature of the third treatment solution is 20°C. Up to 60 .

[0059] <Applications of Polymers Based on Maleic Anhydride>

[0060] In one embodiment, a maleic anhydride-based polymer can be used to prepare a composition that can be used to manufacture a hydrophilic lens. The composition for the lens comprises a maleic anhydride-based polymer and polymerizable monomers. The content of the maleic anhydride-based polymer relative to the total weight of the composition for the lens can be 0.05 wt% to 1 wt%, for example, 0.1 wt%.

[0061] The polymerizable monomer may comprise an alkenyl-containing monomer or a hydrophilic monomer containing an alkenyl group and being hydrophilic. The polymerizable monomer may comprise at least one of a hydrophilic monomer and a siloxane monomer. The siloxane monomer may comprise one or more different siloxane monomers, for example, 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 may be selected from at least one of the group consisting of hydrophilic monomers and siloxane monomers. In one embodiment, the siloxane monomer comprises a siloxane monomer having one methacryloyl group and a siloxane monomer having two methacryloyl groups.

[0062] <Hydrophilic monomers>

[0063] The hydrophilic monomer can be selected from 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), glycidyl methacrylate (GMA), glycerol mono-meth acrylate (GMMA), acrylic acid (AA), N,N-di(methyl meth acrylamide) (DMA), and hexafluoroisopropyl methacrylate. It is one or more of the group consisting of HFMA, N-vinyl-N-methyl acetamide, glycine vinyl carbonate, 2-methacryloyloxyethyl phosphorylcholine, and 2-hydroxy-butyl methacrylate.

[0064] <Silicone Monomer>

[0065] The methacrylic group can be represented as CH 2=C(CH 3)CO-; or, the methacrylic group can be represented as... .

[0066] The siloxane monomer having a single methacrylyl group may be selected from one or more of the group consisting of siloxane monomers represented by formula 1A to formula 1H.

[0067] [Formula 1A]

[0068] [Formula 1B]

[0069] In Equation 1B, aa = 4~80.

[0070] [Formula 1C]

[0071] In Equation 1C, bb = 4~80, cc = 3~40.

[0072] [Formula 1D]

[0073] In Equation 1D, dd = 2~40, ee = 2~40.

[0074] [Formula 1E]

[0075] In Equation 1E, ff = 2~40, gg = 2~40.

[0076] [Formula 1F]

[0077] In Equation 1F, hh = 4~80.

[0078] [Formula 1G]

[0079] In equation 1G, ii = 4~80.

[0080] [Formula 1H]

[0081] In formula 1H, TMS is the abbreviation for trimethylsiloxane.

[0082] The second siloxane monomer having two methacrylic groups may be selected from one or more of the group consisting of siloxane monomers represented by formulas 2A to 2C.

[0083] [Equation 2A]

[0084] In Equation 2A, jj=4~80, kk=1~10, rr=1~10.

[0085] [Formula 2B]

[0086] In Equation 2B, ss = 4~80.

[0087] [Equation 2C]

[0088] In equation 2C, tt = 4~80.

[0089] In one embodiment, the content of a silicate monomer having one methacryl group may be 50 wt% to 91 wt% relative to the total weight of the silicate monomers, and the content of a silicate monomer having two methacryl groups may be 9 wt% to 50 wt%.

[0090] In one embodiment, the composition for the lens may further include an ultraviolet (UV) absorber, and / or an initiator, and / or a blue light absorber. The UV absorber may be selected from UV absorbers known in the art and applicable to contact lens materials. The content of the UV absorber may be 0.01 wt% to 5 wt% relative to the total weight of the composition for the lens. The initiator may be a thermal initiator or a photoinitiator. Both thermal and photoinitiators may be selected from initiators known in the art and applicable to polymerization reactions. The content of the initiator may be 0.45 wt% to 0.75 wt% relative to the total weight of the composition for the lens. The type and amount of blue light absorber added may be selected by those skilled in the art according to actual needs. For example, the blue light absorber may be Reactive Yellow 15. In one embodiment, the content of the blue light absorber may be 0.1 wt% to 5 wt% relative to the total weight of the composition for the lens.

[0091] The above-mentioned components can be mixed in a specific ratio to form a composition for use in contact lenses. In one embodiment, the composition for use in contact lenses can be placed in a contact lens mold, and the components can be cured by heating or light exposure (thermocuring or photocuring) to form a lens. The heating temperature can be approximately 30-150°C. The heating time can be approximately 1-12 hours. After the curing reaction, hydration and / or sterilization can be performed. Hydration may involve immersing the lens in alcohol and pure water, followed by equilibration in a buffer solution.

[0092] <Applications of Polymers Based on Maleic Anhydride>

[0093] In one embodiment, a polymer based on maleic anhydride can be used to prepare a hydrophilic treatment agent, which can be used on lenses. The treatment agent for lenses is, for example, a lens packaging solution (lens delivery solution), a lens cleaning solution, a lens care solution, or a lens disinfectant. A lens packaging solution refers to a solution that is stored in a packaging container along with the lens. Lenses are typically stored in packaging containers containing a packaging solution for sale. The lens packaging solution may be a buffer solution. When the lens comes into contact with the treatment agent, the treatment agent may penetrate the lens interior or adhere to the lens surface, affecting the lens's moisturizing properties and comfort.

[0094] The treatment agent for the lens comprises at least a buffer solution and a maleic anhydride-based polymer. The treatment agent may contain 0.05 wt% to 5 wt% of the maleic anhydride-based polymer, for example, 0.1 wt% to 2 wt%, relative to the total weight of the treatment agent. The buffer solution may contain one or more of boric acid or a salt thereof, glycerol, 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 amino acids.

[0095] In one embodiment, the treatment agent may further comprise a moisturizing lubricant, a vitamin, an osmotic pressure regulator, a surfactant, a cooling agent, or any combination thereof. The moisturizing lubricant may be selected from one or more of the group consisting of methylcellulose (MC), hydroxypropyl methylcellulose (HPMC), hydroxyethyl cellulose, carboxymethyl cellulose (CMC), hyaluronic acid (HA), hyaluronic acid salts, alginate, alginate salts, polymers with phosphorylcholine groups, polyvinylpyrrolidone (PVP), and polydextrose. Polymers with phosphorylcholine groups may, for example, be poly[2-methacryloyloxyethyl phosphorylcholine] (poly-MPC), copolymers of 2-methacryloyloxyethyl phosphorylcholine (MPC) and methacrylic acid ester, or combinations thereof. The content of moisturizing lubricant relative to the total weight of the treatment agent can be 0.01 wt% to 1 wt%.

[0096] The vitamins may be selected from one or more of the group consisting of vitamins A, B, C, D, E, and K. The B vitamins may be selected from one or more of the group consisting of vitamins B1, B2, B3, B6, and B12. The vitamin content relative to the total weight of the treatment agent may be 0.001 wt% to 1 wt%, for example, 0.001 wt% to 0.5 wt%. The osmotic pressure regulator may be selected from one or more of the group consisting of sodium chloride, potassium chloride, calcium chloride, zinc chloride, magnesium chloride, and dextrose. The osmotic pressure regulator content relative to the total weight of the treatment agent may be 0.01 wt% to 2.5 wt%. The osmotic pressure regulator adjusts the osmotic pressure of the treatment agent to make its osmotic pressure close to that of normal tears. The surfactant may be selected from one or more of the group consisting of nonionic surfactants, cationic surfactants, and zwitterionic surfactants. The type and amount of surfactant added can be selected by those skilled in the art according to actual needs. For example, the surfactant content relative to the total weight of the treatment agent can be 0.0001 wt% to 5.0 wt%. The type and amount of cooling agent added can be selected by those skilled in the art according to actual needs. For example, the cooling agent content relative to the total weight of the treatment agent can be 0.0001 wt% to 1.0 wt%.

[0097] In one embodiment, the treatment agent may further comprise a pharmaceutically active ingredient, such as a vasoconstrictor, anti-inflammatory agent, astringent, anti-allergic agent, antibacterial agent, or any combination thereof. The content of the pharmaceutically active ingredient relative to the total weight of the treatment agent may be 0.001 wt% to 5.0 wt%.

[0098] In one embodiment, the treatment agent comprises a maleic anhydride-based polymer, vitamin B, a phosphorocholine-containing polymer, and deionized water. The presence of both vitamin B and the phosphorocholine-containing polymer in the treatment agent can improve the lens's moisturizing effect and comfort.

[0099] The above-mentioned components can be added to deionized water in a specific ratio and mixed evenly to obtain a lens treatment agent.

[0100] To make the above-mentioned objects, features, and advantages of the present invention more apparent and understandable, specific examples are provided below for detailed explanation:

[0101] <Polymers Based on Maleic Anhydride>

[0102] The maleic anhydride-based polymer (hereinafter also referred to as the product) was manufactured according to the components and proportions described in Table 1 below using the aforementioned manufacturing method. The examples and comparative examples in 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 at a ratio of 1% to a measured amount of water, its solubility was observed visually, and the content of the third repeating unit was determined by titration.

[0103] The representative product is soluble in water, and the solution is transparent. The representative product cannot be completely dissolved in water, and the solution is white and turbid.

[0104] [Table 1] Compounds containing maleic anhydride: Polyethylene methacrylate (molar ratio) Content of the third repeating unit (wt%) water solubility Example 1 8:2 8.0 Example 2 7:3 7.4 Example 3 6:4 6.2 Example 4 3:7 2.5 Example 5 1:9 0.8 Comparative Example 1 10:0 N / A Comparative Example 2 9:1 N / A

[0105] Comparative Example 1 used maleic anhydride to form polymaleic anhydride (i.e., a polymer not modified with polyethylene methacrylate) and tested its water solubility. The results showed poor solubility and precipitation. In Comparative Example 2, the amount of maleic anhydride-containing compound was too high, resulting in poor water solubility and precipitation. Furthermore, due to precipitation, the content of its third repeating unit could not be determined by titration. The maleic anhydride-based polymers of Examples 1-5 were all soluble in water without precipitation or turbidity, demonstrating that the present invention, using a specific proportion of polyethylene methacrylate for modification, can effectively improve solubility. Moreover, modification with polyethylene methacrylate does not open the ring structure of the maleic anhydride functional groups, thus maintaining the reactivity of the maleic anhydride functional groups. Opened ring-shaped maleic anhydride functional groups are difficult to bond with other materials (e.g., amine-containing polymers) in subsequent hydrophilic coating processes, thus failing to form a stable hydrophilic coating.

[0106] In addition to visual inspection, a dynamic light scattering (DLS) instrument can be used to detect the transmittance (%) of the product aqueous solution (the product is added to a quantitative amount of water at a ratio of 1% to form the product aqueous solution). The test results show that the product aqueous solution of the embodiment has a transmittance of more than 86%, while the product aqueous solution of Comparative Example 2 has a transmittance of less than 86%, indicating that the water solubility of the product of the embodiment is better than that of the product of the comparative example.

[0107] Lenses with hydrophilic coating

[0108] The maleic anhydride-based polymers of Examples 1-5 were manufactured according to the components and proportions listed in Table 1 using the aforementioned manufacturing method. These polymers were then used in the aforementioned method for manufacturing lenses with hydrophilic coatings to produce lenses with hydrophilic coatings of Examples 1A-5B. The components used in the manufacturing method of lenses with hydrophilic coatings are shown in Table 2 below. Examples 1A and 1B use the maleic anhydride-based polymer of Example 1, and the lens of Example 1B further includes a base layer. Examples 2A and 2B use the maleic anhydride-based polymer of Example 2, and the lens of Example 2B further includes a base layer. Examples 3A and 3B use the maleic anhydride-based polymer of Example 3, and the lens of Example 3B further includes a base layer. Examples 4A and 4B use the maleic anhydride-based polymer of Example 4, and the lens of Example 4B further includes a base layer. Examples 5A and 5B use the maleic anhydride-based polymer of Example 5, and the lens of Example 5B further includes a base layer. Comparative Example 3 is a lens without a hydrophilic coating and a base layer (untreated lens). The embodiments and comparative examples in Table 2 use silicone gel contact lenses of the same composition as the lens body.

[0109] [Table 2] Polymers based on maleic anhydride Amine-containing polymers Second polymer Water contact angle Example 1A Example 1 Polyethyleneimine -- 94 Example 1B Example 1 Polyethyleneimine Polyacrylic acid 80 Example 2A Example 2 Polyethyleneimine -- 93 Example 2B Example 2 Polyethyleneimine Polyacrylic acid 41 Example 3A Example 3 Polyethyleneimine -- 88 Example 3B Example 3 Polyethyleneimine Polyacrylic acid 58 Example 4A Example 4 Polyethyleneimine -- 76 Example 4B Example 4 Polyethyleneimine Polyacrylic acid 60 Example 5A Example 5 Polyethyleneimine -- 80 Example 5B Example 5 Polyethyleneimine Polyacrylic acid 73 Comparative Example 3 -- -- -- 100

[0110] The manufacturing methods and conditions used in the embodiments and comparative examples in Table 2 are as follows: The amine-containing polymer is dissolved in ethanol and deionized water, and the mixture is homogeneous to obtain the first treatment solution. The maleic anhydride-based polymer is dissolved in deionized water, and the mixture is homogeneous to obtain the second treatment solution. The second polymer is dissolved in ethanol and deionized water, and the mixture is homogeneous to obtain the third treatment solution. The 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. The lens structure, including the hydrophilic coating and the lens itself, is removed from the second treatment solution and placed in a buffer solution for sealing and sterilization. The sterilization conditions are 125°C. 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 in the first treatment solution.

[0111] The water contact angle of the lenses of Examples 1A to 5B and Comparative Example 3 was tested, and the results are listed in Table 2 above.

[0112] <Water Contact Angle Detection>

[0113] Place the lens on a cleanroom cloth and press the lens structure through the cloth for 10 seconds to remove moisture from the lens surface. Then use a contact angle meter. The company manufactures a DSA25 (model number) to measure the angle between the surface of a water droplet and the surface of a lens (water contact angle). The larger the water contact angle, the more hydrophobic the lens surface; the smaller the water contact angle, the more hydrophilic the lens surface.

[0114] The water contact angles of the lenses in Examples 1A to 5B are all smaller than that of the lens in Comparative Example 3, indicating that the lens surface of the present invention has high hydrophilicity. The lenses in Examples 2B, 3B, and 4B all have... The following water contact angles indicate that the base layer can further enhance the hydrophilicity of the lens. Furthermore, the lenses of Examples 1B, 2B, 3B, 4B, and 5B were tested for staining using Sudan dye solution. The results showed that the lenses of Examples 1B, 2B, 3B, 4B, and 5B were not stained by the Sudan dye solution or were only slightly stained, indicating that the base layer can enhance the lens's anti-oil adsorption properties. As shown in Table 2, the lens surface of the present invention has high hydrophilicity and anti-oil adsorption properties, which can effectively improve the user's wearing comfort and alleviate dryness, infection, and eye damage.

[0115] <Agent for lens treatment>

[0116] The components listed in Table 3 were mixed according to the proportions in the table, stirred until no undissolved matter was observed in the solution, to prepare a lens treatment agent. The maleic anhydride-based polymer in Table 3 is the same as the maleic anhydride-based polymer used in Example 1, with deionized water as the solvent. 1 mL of the lens treatment agent was placed in a packaging container, the lens was immersed in the treatment agent in the packaging container, and the aluminum foil was heat-sealed onto the packaging container before sterilization. The sterilization conditions were as described above. The water contact angle of the lenses from Examples 6-10 and Comparative Example 4 was tested, and the results are listed in Table 3. The water contact angle test was performed as described above. The treatment agents shown in Examples 6-10 can be used as packaging solutions for lenses.

[0117] [Table 3] Example Comparative example 6 7 8 9 10 4 Polymers based on maleic anhydride (wt%) 0.1 0.5 0.8 1 2 -- Boric acid (wt%) 0.4 0.4 0.4 0.4 0.4 0.4 Sodium borate (wt%) 0.05 0.05 0.05 0.05 0.05 0.05 Sodium chloride (wt%) 0.7 0.7 0.7 0.7 0.7 0.7 Vitamin B12 (wt%) -- -- -- 0.004 -- -- Hyaluronic acid (wt%) -- -- -- -- 0.01 -- Water contact angle 100 93 89 85 78 105

[0118] As shown in Table 3, the water contact angle of the lenses in Examples 6 to 10 is smaller than that of the lens in Comparative Example 4, indicating that storing the lenses in the treatment agent of the present invention can improve the hydrophilicity of the lens surface and improve the wearing comfort of the user.

[0119] <Components used in lenses>

[0120] In Example 11, the composition for the lens contained 0.1 wt% of a maleic anhydride-based polymer (relative to the total weight of the composition) and hydrophilic monomers and silicate monomers. In Comparative Example 5, the composition for the lens contained only hydrophilic monomers and silicate monomers and did not contain a maleic anhydride-based polymer. Example 11 and Comparative Example 5 used the same hydrophilic monomers and silicate monomers and were manufactured using the aforementioned manufacturing method to produce the composition for the lens. The compositions for the lens from Example 11 and Comparative Example 5 were placed into a contact lens mold and manufactured into lenses using the aforementioned manufacturing method. The water contact angle of the lenses was measured (the water contact angle measurement was performed as described above). It was found that the water contact angle of the lens from Example 11 was 82°. The water contact angle of the lens in Comparative Example 5 is 85°. This indicates that using the maleic anhydride-based polymer of the present invention in the composition of lenses can indeed improve the hydrophilicity of the lens surface.

[0121] Therefore, the maleic anhydride-based polymer proposed in this invention can effectively improve the solubility of maleic anhydride-based polymers while maintaining the reactivity of maleic anhydride functional groups. The lens, lens treatment agent, and lens composition proposed in this invention can effectively improve hydrophilicity and resistance to oil adsorption, thereby improving wearing comfort and reducing problems such as reduced clarity caused by oil adhering to the lens surface. It also offers advantages such as simple manufacturing process, low cost, and high yield.

[0122] In summary, although the present invention has been disclosed above with reference to embodiments, it is not intended to limit the invention. Those skilled in the art can make various modifications and refinements without departing from the spirit and scope of the invention. Therefore, the scope of protection of the present invention shall be determined by the appended claims.

[0123] 10: Lens body 11: Front surface 12: Back surface 13: Edge 20: Hydrophilic coating 20S1: First side 20S2: Second side 30: Basal layer 100, 200: Lenses D1: Normal direction S: Outer surface

Claims

1. A maleic anhydride-based polymer, represented by the following formula A: [Formula A], wherein Ra is H or C1-C3 alkyl, z, m, p are integers or non-integers greater than or equal to 1, and the content of the repeating unit in Formula A is from 0.5 wt% to 9 wt% based on the total weight of the maleic anhydride-based polymer.

2. The maleic anhydride-based polymer as claimed in claim 1, wherein the content of the repeating unit in formula A is from 0.8 wt% to 8 wt% based on the total weight of the maleic anhydride-based polymer.

3. The maleic anhydride-based polymer as claimed in claim 1, wherein the mole ratio of the repeating unit to the repeating unit in formula A is 0.5 to 50.

4. The maleic anhydride-based polymer as described in claim 3, wherein the mole ratio of the repeating unit to the repeating unit is 2 to 30.

5. The maleic anhydride-based polymer as claimed in claim 1, wherein the weight-average molecular weight of the maleic anhydride-based polymer is between 5,000 and 1,500,000.

6. The maleic anhydride-based polymer as described in claim 1, wherein z is between 4 and 50, m is between 10 and 50, and p is between 1 and 20.

7. A lens having a hydrophilic coating, comprising: a lens body; and a hydrophilic coating at least partially formed on an outer surface of the lens body, wherein the hydrophilic coating comprises a first polymer represented by formula B: [Formula B], wherein Ra is H or a C1-C3 alkyl group, R1 is H or a substituent comprising at least one of a primary amino group, a secondary amino group, and a tertiary amino group, R2 is a substituent comprising at least one of a primary amino group, a secondary amino group, and a tertiary amino group, and z, m, and q are integers or non-integers greater than or equal to 1.

8. A lens with a hydrophilic coating as described in claim 7, wherein the mole ratio of the repeating unit in formula B to the repeating unit is 0.5 to 50.

9. A lens with a hydrophilic coating as described in claim 7, wherein the mole ratio of the repeating unit to the repeating unit is 2 to 30.

10. The lens having a hydrophilic coating as described in claim 7, further comprising a base layer formed between the lens body and the hydrophilic coating, wherein the base layer comprises a second polymer having carboxyl groups.

11. A lens with a hydrophilic coating as described in claim 7, 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 lenses, comprising a buffer solution and a maleic anhydride-based polymer as described in claim 1.

13. The treatment agent as described in claim 12 further comprises at least one of a moisturizing lubricant and a vitamin.

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

15. A composition for a lens comprising: a maleic anhydride-based polymer as described in claim 1 and a polymerizable monomer.

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

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