Silicone hydrogel contact lenses

Abstract

A silicone hydrogel contact lens is provided that exhibits high oxygen permeability and high water content. [Solution] A silicone hydrogel contact lens comprising a polymer composition prepared by polymerization of a silicone hydrogel contact lens-forming composition, the silicone hydrogel contact lens-forming composition comprising about 10 to about 40% by weight of a silicon-containing macromer, about 1 to about 20% by weight of polyethylene glycol having a molecular weight of about 200 to about 1,000 g / mol, and a crosslinking agent or initiator, and the polymerization is carried out by thermal polymerization at a temperature of about 100°C to about 110°C or UV photopolymerization in a manner such that at least about 95% of the polyethylene glycol is removed from the polymer composition.

Description

[Technical Field]

[0001] This disclosure relates to a composition for forming silicone hydrogel contact lenses, a silicone hydrogel contact lens manufactured from the composition, and a method for manufacturing the composition or a silicone hydrogel contact lens. [Background technology]

[0002] Contact lenses are widely used for cosmetic purposes in addition to vision correction, and the market for cosmetic contact lenses continues to grow. Research into developing new cosmetic contact lenses is active, resulting in a constant stream of new products with various physical properties. Zanini et al., U.S. Patent No. 7,789,507, discloses an ophthalmic lens formed from a reaction mixture comprising a high molecular weight hydrophilic polymer, an effective amount of hydroxyl-functionalized silicone-containing monomer, and an effective amount of polyethylene glycol to facilitate the release of the lens from the device forming mold component, wherein the polyethylene glycol comprises one or more of PEG2000, mPEG, and PEGDME. [Overview of the Initiative] [Problems that the invention aims to solve]

[0003] In one embodiment, a composition is provided for manufacturing a silicone hydrogel contact lens exhibiting high oxygen permeability and high water content. In another embodiment, a silicone hydrogel contact lens exhibiting high oxygen permeability and high water content is provided. In yet another embodiment, a method for producing silicone hydrogel contact lenses and compositions according to this specification is provided. [Means for solving the problem]

[0004] In one embodiment, a silicone hydrogel contact lens comprising a polymer composition prepared by polymerization of a silicone hydrogel contact lens forming composition comprises about 10 to about 40% by weight of a silicon-containing macromer, about 1 to about 20% by weight of polyethylene glycol having a molecular weight of about 200 to about 1,000 g / mol, and a crosslinking agent or initiator, wherein the polymerization is carried out by thermal polymerization at a temperature of about 100°C to about 110°C or by UV photopolymerization, thereby removing at least about 95% of the polyethylene glycol from the polymer composition.

[0005] In one embodiment, a contact lens polymer composition prepared by polymerization of a silicone hydrogel contact lens forming composition comprises about 10 to about 40% by weight of silicon macromer, about 1 to about 20% by weight of polyethylene glycol having a molecular weight of about 200 to about 1,000 g / mol, and a crosslinking agent or initiator, wherein the polymerization is carried out by thermal polymerization at a temperature of about 100°C to about 110°C or by UV photopolymerization, in which at least about 95% of the polyethylene glycol is removed from the polymer composition.

[0006] In one embodiment, the method for preparing the polymer composition includes a step of polymerization of a silicone hydrogel contact lens forming composition comprising about 10 to about 40% by weight of a silicon macromer, about 1 to about 20% by weight of polyethylene glycol having a molecular weight of about 200 to about 1,000 g / mol, and a crosslinking agent or initiator, wherein the polymerization is carried out in such a manner that at least about 95% of the polyethylene glycol is removed from the polymer composition by thermal polymerization at a temperature of about 100°C to about 110°C or by UV photopolymerization.

[0007] This disclosure is not limited to the embodiments described above and includes other purposes and benefits not mentioned. Embodiments of this disclosure may provide a clearer understanding of this disclosure.

[0008] Some of the other embodiments are defined in the following description, some of which will become clear from the description or can be learned through the embodiment.

Advantages of the Invention

[0009] In one embodiment, a composition for manufacturing a silicone hydrogel contact lens exhibiting high oxygen permeability and high water content is provided.

Modes for Carrying Out the Invention

[0010] Hereinafter, embodiments of the present disclosure will be described in detail so that those skilled in the art to which the present disclosure pertains can easily implement them. Since the present disclosure can be embodied in various forms, it should not be construed as being limited to the embodiments described herein.

[0011] The cornea receives oxygen by contacting oxygen dissolved in tears or oxygen in the air. However, a contact lens placed on the cornea may interfere with the supply of oxygen. Therefore, the oxygen permeability of a contact lens is an important consideration, especially when developing a new contact lens for improving eye health.

[0012] Also, in the case of a contact lens material, a composition containing a mixture of a plurality of monomers and an initiator is injected into a mold and polymerized while causing a crosslinking reaction by instantaneous energy. The lens is formed by a polymer material generated by the polymerization reaction, and the properties of the contact lens such as refractive index, mechanical strength, wettability, and oxygen permeability are determined by the components of the composition.

[0013] <Definition> As used herein, the term "hydrogel" refers to a crosslinked polymer material that can retain at least 10% by weight or more of water in the matrix of the crosslinked polymer when hydrated. As used herein, the "silicon-containing macromer" is a monomer containing silicon and having an ethylenically unsaturated group, and refers to a macromer having a weight average molecular weight of 500 Da or more. As used herein, "polyethylene glycol" is represented by the formula H-(O-CH2-CH2)n-OH. Generally, n has a value of 4 or more. As used herein, the "hydrophilic monomer" refers to a monomer having a polymerizable functional group such as an olefin group or an acrylic group, and a hydrophilic functional group such as a hydroxyl group, an amine, or a pyrrolidone, and having a molecular weight of less than 500 Da. As used herein, the "silicon-containing monomer" refers to a monomer containing silicon and having an ethylenically unsaturated group, and having a weight-average molecular weight of less than 500 Da.

[0014] <Silicone hydrogel contact lens and polymer composition> The present disclosure provides a silicone hydrogel contact lens comprising a polymer composition prepared by polymerization of a composition for forming a silicone hydrogel contact lens. The composition for forming a silicone hydrogel contact lens comprises about 10 to about 40% by weight of a silicon-containing macromer, about 1 to about 20% by weight of polyethylene glycol having a molecular weight of about 两百 to about 1,000 g / mol, and a crosslinking agent or an initiator, and the polymerization is carried out by thermal polymerization or UV photopolymerization at a temperature of about 100 °C to about 110 °C in such a manner that at least about 95% of the polyethylene glycol is removed from the polymer composition.

[0015] The polyethylene glycol in the composition for forming a silicone hydrogel contact lens may be any PEG having a molecular weight of about 两百 to about 1,000 g / mol. For the production of silicone hydrogel contact lenses, it is not desirable to use high molecular weight polyethylene glycols such as, for example, 2,000 to 6,000 g / mol. This is because such high molecular weight PEGs are not sufficiently removed from the composition during polymerization, and the resulting polymer cannot achieve desired properties such as high oxygen permeability and high water content. In one embodiment, the polyethylene glycol is selected from the group consisting of PEG200, PEG300, PEG400, PEG600, PEG800, and PEG100]. In a particular embodiment, the polyethylene glycol is PEG200, PEG400, or PEG1000.

[0016] The polymer composition is prepared by polymerization of a silicone hydrogel contact lens forming composition. In one embodiment, polymerization is carried out by thermal polymerization at a temperature of about 100°C to about 110°C. In another embodiment, polymerization is carried out by UV photopolymerization.

[0017] In various embodiments, the polymerization step is carried out in such a manner that at least about 95% of polyethylene glycol is removed from the polymer composition. The polyethylene glycol removal rate is measured based on the initial amount of polyethylene glycol contained in the composition before polymerization. In other words, PEG removal rate = 100 - amount of PEG remaining after polymerization / amount of PEG before polymerization × 100%. In some embodiments, polymerization is carried out to remove about 95%, 96%, or 97% of polyethylene glycol from the composition.

[0018] In some embodiments, the silicone hydrogel contact lens has a water content of about 40% to about 65%. In various embodiments, the silicone hydrogel contact lens has a water content of about 40%, about 45%, about 50%, about 55%, about 60%, or about 65%.

[0019] In some embodiments, the silicone hydrogel contact lens has an oxygen permeability (Dk) of about 70 to about 120. In various embodiments, the silicone hydrogel contact lens has an oxygen permeability (Dk) of about 70, about 75, about 80, about 85, about 90, about 95, about 100, about 105, about 110, about 115, or about 120.

[0020] In some embodiments, the composition for forming silicone hydrogel contact lenses comprises about 10 to about 40% by weight of a silicon-containing macromer, about 1 to about 20% by weight of polyethylene glycol, about 10 to about 50% by weight of a hydrophilic monomer, about 10 to about 20% by weight of a silicon-containing monomer, and a crosslinking agent or initiator, and the silicone hydrogel contact lenses described herein have various improved properties, such as oxygen permeability and water content.

[0021] The morphology of silicone hydrogel contact lenses, determined by adjusting the compatibility between monomers, influences the physical properties of the silicone hydrogel contact lenses and contributes to production efficiency and quality stabilization. Compatibility between monomers can be calculated using the difference in thermodynamic energies, such as the Flory-Huggins ratio. To improve the accuracy of the calculation, three factors—dispersion, polarity, and hydrogen bonding—are used to determine the degree of compatibility. Hydrogen bonding is considered because it can further improve the accuracy of the degree of compatibility calculation. Therefore, the Hansen solubility parameter is used as a means of predicting compatibility.

[0022] Silicon-containing polymers are known to have high oxygen permeability, and contact lenses made from silicone materials generally have high oxygen permeability. However, such contact lenses typically have low water content due to the hydrophobicity of the polymer material. Increasing the amount of hydrophilic monomers in the polymer to raise the water content will again decrease oxygen permeability. Thus, in conventional contact lenses using silicone materials, oxygen permeability and water content are in a cancel-out relationship. In other words, it is difficult to manufacture contact lenses that achieve both high oxygen permeability and high water content.

[0023] The silicone hydrogel contact lenses of this disclosure are prepared by polymerizing a silicon-containing macromer, and are able to satisfactorily achieve both oxygen permeability and water content.

[0024] In one embodiment, the silicone hydrogel contact lens forming composition comprises a silicon-containing macromer and polyethylene glycol, and the differences ΔδD, ΔδP, and ΔδH of the dispersion force (δD), dipole attractive force (δP), and hydrogen bonding force (δH) that determine the Hansen solubility parameter of the silicon-containing macromer and polyethylene glycol, respectively, satisfy the following conditions. -6.0MPa 1 / 2 ≤ΔδD ≤ ​​1.0MPa 1 / 2 1.5 MPa 1 / 2 ≤ΔδP ≤ 3.5MPa 1 / 2 4.0 MPa 1 / 2 ≦ΔδH≦8.0 MPa 1 / 2

[0025] The silicone hydrogel contact lens according to an embodiment of the present disclosure includes a polymer obtained by polymerizing a composition for forming a silicone hydrogel contact lens, and the composition includes a silicon-containing macromer and polyethylene glycol. The differences ΔδD, ΔδP, and ΔδH in the dispersive force (δD), dipole-dipole force (δP), and hydrogen bonding force (δH) that define the Hansen solubility parameter in the Hansen solubility parameters of the silicon-containing macromer and polyethylene glycol respectively satisfy the following conditions. -6.0 MPa 1 / 2 ≦ΔδD≦1.0 MPa 1 / 2 1.5 MPa 1 / 2 ≦ΔδP≦3.5 MPa 1 / 2 4.0 MPa 1 / 2 ≦ΔδH≦8.0 MPa 1 / 2

[0026] Polyethylene glycol is used as a processing aid during the polymerization of the silicone hydrogel contact lens and plays roles such as dispersion, thickening, and high curing depending on the type of material for forming the polymer. Also, polyethylene glycol can greatly affect the properties of the polymer formed by the composition ratio of the composition. Non-reactive polyethylene glycol changes in gyration radius and size due to its compatibility with other components in the composition from the start of the reaction, and the compatibility between polyethylene glycol and the polymer may change. Then, through the hydration process, non-reactive polyethylene glycol escapes, and a structure formed with a specific size and molecular arrangement depending on the gyration radius remains. The structure formed by the gyration radius affects the physical properties of the contact lens.

[0027] Therefore, in compositions for forming silicone hydrogel contact lenses, polyethylene glycol is involved in controlling the properties of the hydrogel by controlling the solubility of the silicon-containing macromer in polyethylene glycol. As a result, silicone hydrogel contact lenses can achieve high oxygen permeability and high water content. The solubility of the silicon-containing macromer in polyethylene glycol is controlled so that the three control factors that determine the Hansen solubility parameter, namely dispersion force (δD), dipole attraction force (δP), and hydrogen bonding force (δH), satisfy the above ranges.

[0028] Specifically, polyethylene glycol undergoes phase separation due to decreased compatibility with the polymer produced during the polymerization process of the silicone hydrogel contact lens composition. After the polymerization reaction is complete, polyethylene glycol is isolated during the hydration process, forming voids in the polymer chain. These voids are then filled with water, resulting in a high water content.

[0029] By adjusting the solubility between silicon-containing macromers and polyethylene glycol to satisfy the Hansen solubility parameter conditions, polyethylene glycol plays a role in providing hydration sites that determine the water content.

[0030] Therefore, considering that the silicone hydrogel contact lenses of this disclosure are made from a silicon-containing macromer-based polymer, the silicone hydrogel contact lenses have high oxygen permeability. Furthermore, as described above, silicone hydrogel contact lenses can achieve both high oxygen permeability and high water content by increasing the water content using polyethylene glycol during polymerization.

[0031] The Hansen solubility parameter (HSP) consists of three parameters representing the forces acting between molecules of a substance (dispersion force δD, dipole attraction force δP, and hydrogen bonding force δH), and can be calculated according to the method presented by Charles Hansen in "Hansen Solubility Parameters: A User's Handbook," 2nd edition (2007), Boca Raton, Fla., CRC Press (ISBN 978-O-8493-7248-3).

[0032] Dispersive force (δD) quantifies the energy of intermolecular dispersion forces, i.e., van der Waals forces. Dipole attractive force (δP) represents the energy of intermolecular dipole interactions. Hydrogen bonding force (δH) quantifies the energy derived from intermolecular hydrogen bonds, i.e., the ability to interact via hydrogen bonds.

[0033] Hansen solubility parameters (HSPs) are vector quantities represented by δD, δP, and δH, and are plotted on a three-dimensional space (Hansen space) with the three parameters as coordinate axes. For example, the Hansen solubility parameters (HSPs) of commonly used materials can be obtained by referring to known information sources such as databases. For materials for which Hansen solubility parameters (HSPs) are not registered in the database, the Hansen solubility parameters (HSPs) can be calculated from the chemical structure of the substance or the Hansen solubility method using computer program software such as Hansen Solubility Parameters in Practice (HSPiP). Specifically, the Hansen solubility parameters of silicon-containing macromers may be calculated according to the Y-BM Group Contribution method, and similarly, the solubility parameters of other components of silicone hydrogel contact lens compositions, such as polyethylene glycol and other single molecules of polymers, may be calculated and used.

[0034] To control the solubility of silicon-containing macromers in polyethylene glycol, i.e., to determine the Hansen solubility parameter, three parameters—dispersion force (Δd), dipole attraction (δP), and hydrogen bonding force (δH)—are used at -6.0 MPa. 1 / 2 ≤ΔδD ≤ ​​1.0MPa 1 / 2 , 1.5 MPa 1 / 2 ≤ΔδP ≤ 3.5MPa 1 / 2 , 4.0 MPa 1 / 2 ≤ ΔδH ≤ 8.0 MPa 1 / 2 To satisfy the above conditions, variables that affect the values ​​of dispersion force (Δd), dipole attraction force (δP), and hydrogen bonding force (δH) may be controlled. For example, variables such as the formulation and amount of each component of the silicone hydrogel contact lens forming composition, the structure and molecular weight of the silicon-containing macromer, and the molecular weight and content of polyethylene glycol can complexly affect the above conditions. Therefore, the silicone hydrogel contact lens forming composition can be designed to satisfy the above conditions by controlling these variables.

[0035] In a silicone hydrogel contact lens according to another embodiment of the present invention, the difference ΔδD, ΔδP, and ΔδH of the dispersion force (δD), dipole attraction force (δP), and hydrogen bonding force (δH) that determine the Hansen solubility parameter for the silicon-containing macromer and polyethylene glycol, respectively, is -0.8 MPa. 1 / 2 ≤△δD≤0.3MPa 1 / 2 , 2.0 MPa 1 / 2 ≤ΔδP ≤ 2.5MPa 1 / 2 , 4.5 MPa 1 / 2 ≤ΔδH ≤ 5.7MPa 1 / 2 It may satisfy the range.

[0036] In one embodiment, the silicon-containing macromer comprises at least several siloxane repeating units [-Si-O-] and one or two acrylic functional groups.

[0037] In one embodiment, the weight-average molecular weight of the silicon-containing macromer may be in the range of about 500 Da to about 2,500 Da.

[0038] Specific examples of silicon-containing macromers include, but are not limited to, methacryloxypropyltris(trimethylsiloxy)silane, monomethacryloxyalkyl-terminated polydimethylsiloxane, 3-{α-(trimethylsilyl)poly[oxy(dimethylsilylene)]}propyl 2-methylpropa-2-enoate, monobutyl-terminated polydimethylsiloxane, methacryloxypropyl-terminated polydimethylsiloxane, monovinyl-terminated polydimethylsiloxane, bis(divinyl)-terminated polydimethylsiloxane, and α-monovinyl-monophenyl-Ω-monohydride-terminated polymethylsiloxane. A silicon-containing macromer may contain at least one of these substances.

[0039] In one embodiment, the silicon-containing macromer may include at least one selected from the compound represented by the following chemical formula 1, the compound represented by the following chemical formula 2, the compound represented by the following chemical formula 3, the compound represented by the following chemical formula 4, and combinations thereof.

[0040] [ka] In chemical formula 1, a is an integer from 1 to 30, b is an integer from 1 to 30, and c is an integer from 5 to 30. R1 to R4 are each independently hydrogen or a C1-C6 alkyl group, and R5 is a C1-C8 alkyl group, tri(C1-C8)alkylsiloxy, phenyl, naphthyl, substituted C1-C8 alkyl group, substituted phenyl, or substituted naphthyl. The substituents on the alkyl group are at least one selected from C1-C8 alkoxycarbonyl, C1-C8 alkyl, C1-C8 alkoxy, amide, halogen, hydroxyl, carboxyl, C1-C8 alkylcarbonyl, and formyl. The substituents on the phenyl and naphthyl groups are at least one selected from C1-C8 alkoxycarbonyl, C1-C8 alkyl, C1-C8 alkoxy, amide, halogen, hydroxyl, carboxyl, C1-C8 alkylcarbonyl, and formyl, respectively.

[0041] [ka] In chemical formula 2, a is an integer from 1 to 27, b is an integer from 3 to 27, R1 and R2 are each independently hydrogen or C1-C8 alkyl, R3 and R4 are each independently hydrogen, C1-C6 alkyl, tri(C1-C6)alkylsiloxy, phenyl, naphthyl, substituted C1-C6 alkyl, substituted phenyl, or substituted naphthyl, the alkyl substituent is at least one selected from C1-C6 alkoxycarbonyl, C1-C6 alkyl, C1-C6 alkoxy, amide, halogen, hydroxyl, carboxyl, C1-C6 alkylcarbonyl, and formyl, and the phenyl and naphthyl substituents are each at least one selected from C1-C6 alkoxycarbonyl, C1-C6 alkyl, C1-C6 alkoxy, amide, halogen, hydroxyl, carboxyl, C1-C6 alkylcarbonyl, and formyl.

[0042] [ka] In chemical formula 3, a is an integer from 1 to 27, b is an integer from 3 to 27, R1 and R2 are each independently hydrogen or C1-C8 alkyl, R3 and R4 are each independently hydrogen, C1-C6 alkyl, tri(C1-C6)alkylsiloxy, phenyl, naphthyl, substituted C1-C6 alkyl, substituted phenyl, or substituted naphthyl, the alkyl substituent is at least one selected from C1-C6 alkoxycarbonyl, C1-C6 alkyl, C1-C6 alkoxy, amide, halogen, hydroxyl, carboxyl, C1-C6 alkylcarbonyl, and formyl, and the phenyl and naphthyl substituents are each at least one selected from C1-C6 alkoxycarbonyl, C1-C6 alkyl, C1-C6 alkoxy, amide, halogen, hydroxyl, carboxyl, C1-C6 alkylcarbonyl, and formyl.

[0043] [ka] In chemical formula 4, a is an integer from 1 to 8, b is an integer from 3 to 10, R1 to R4 are each independently hydrogen or C1-C6 alkyl, R5 is C1-C8 alkyl, tri(C1-C8)alkylsiloxy, phenyl, naphthyl, substituted C1-C8 alkyl, substituted phenyl, or substituted naphthyl, the alkyl substituent is at least one selected from C1-C8 alkoxycarbonyl, C1-C8 alkyl, C1-C8 alkoxy, amide, halogen, hydroxyl, carboxyl, C1-C8 alkylcarbonyl, and formyl, and the phenyl and naphthyl substituents are at least one selected from C1-C8 alkoxycarbonyl, C1-C8 alkyl, C1-C8 alkoxy, amide, halogen, hydroxyl, carboxyl, C1-C8 alkylcarbonyl, and formyl, respectively.

[0044] The type and content of silicon-containing macromers can be freely determined within the range that satisfies the conditions of the Hansen solubility parameter for polyethylene glycol.

[0045] The silicone hydrogel contact lens forming composition may contain approximately 21% to 48% by weight of silicon-containing macromer.

[0046] In one embodiment, the weight-average molecular weight of polyethylene glycol may be in the range of about 200 g / mol to about 1,000 g / mol.

[0047] The polyethylene glycol content may vary depending on the relationship with the silicon-containing macromer in order to satisfy the Hansen solubility parameter requirements for the macromer. For example, a silicone hydrogel contact lens forming composition may contain about 4 to about 96 parts by weight of polyethylene glycol per 100 parts by weight of silicon-containing macromer.

[0048] The type, molecular weight, and content of polyethylene glycol may be freely determined within the range that satisfies the conditions of the Hansen solubility parameter for silicon-containing macromers.

[0049] The physical properties of the final contact lens product are determined by how the composition of each component of the silicone hydrogel contact lens forming composition is designed. While three factors are important when designing the physical properties of a contact lens—water content, oxygen permeability, and durability—other beneficial factors may also exist. In the case of durability, strength, elongation, and Young's modulus may be distinguished. Considering these physical properties of contact lenses, the silicone hydrogel contact lens forming composition may contain other components in addition to the silicon-containing macromer and polyethylene glycol, as long as the composition satisfies the specified Hansen solubility parameter conditions.

[0050] In one embodiment, the silicone hydrogel contact lens forming composition may further contain a hydrophilic monomer.

[0051] Hydrophilic monomers are involved in the radical polymerization of silicone hydrogel contact lens-forming compositions, and the polymer contains structural units based on hydrophilic monomers. Silicon-containing macromers and hydrophilic monomers polymerize to form polymers through radical polymerization reactions induced by heat or light.

[0052] The hydrophilic monomer may be, for example, N,N-dimethylacrylamide, 2-hydroxyethyl methacrylate, glycerol monomethacrylate, 2-hydroxyethyl methacrylate, polyethylene glycol monomethacrylate, methacrylic acid, acrylic acid, N-vinylpyrrolidone, N-vinyl-N-methylacetamide, N-vinyl-N-ethylacetamide, N-vinyl-N-ethylformamide, or N-vinylformamide, but is not limited to these, and may include at least one of these materials.

[0053] In one embodiment, the silicone hydrogel contact lens forming composition may contain about 20 to 239 parts by weight of hydrophilic monomer per 100 parts by weight of silicon-containing macromer. As long as the hydrophilic monomer content of the silicone hydrogel contact lens forming composition is within the above range, it is possible to create a contact lens with a high water content, although not significantly higher than that of commercially available contact lenses.

[0054] In one embodiment, the silicone hydrogel contact lens forming composition may further contain a silicon monomer and a crosslinking agent.

[0055] In one embodiment, the silicon-containing monomer comprises at least a plurality of siloxane repeating units [-Si-O-] and one or two acrylic functional groups.

[0056] Silicon-containing monomers have a weight-average molecular weight of less than 500 Da, are not macromers, and are different from silicon-containing macromers.

[0057] The silicon-containing monomer may be α,ω-bismethacryloxypropyl polydimethylsiloxane (SiGMA), 3-methacryloxypropyl tris(trimethylsiloxy)silane (TRIS), monomethacryloxypropyl-terminated polydimethylsiloxane, polydimethylsiloxane, 3-methacryloxypropyl bis(trimethylsiloxy)methylsilane, or methacryloxypropyl pentamethyldisiloxane, but is not limited to these, and may contain at least one of these materials.

[0058] In one embodiment, the silicone hydrogel contact lens forming composition may contain about 23 to about 143 parts by weight per 100 parts by weight of silicon-containing macromer.

[0059] In one embodiment, the silicone hydrogel contact lens forming composition may further contain a crosslinking agent.

[0060] The crosslinking agent may be, for example, allyl methacrylate (AMA), divinylbenzene (DVB), triethylene glycol dimethacrylate (TrEGDMA), triallyl isocyanurate (TAIC), ethylene glycol dimethyl acrylate (EGDMA), ethylenediamine dimethacrylamide, or glycerol dimethacrylate, but is not limited to these, and may include at least one of these materials.

[0061] In one embodiment, the silicone hydrogel contact lens forming composition may contain about 1 to about 38 parts by weight of a crosslinking agent per 100 parts by weight of silicon macromer.

[0062] In one embodiment, the silicone hydrogel contact lens forming composition may further contain an initiator. The initiator may be a thermal initiator or a photoinitiator that initiates a radical reaction by heat or light such as infrared or ultraviolet rays.

[0063] Examples of initiators include compounds such as lauryl peroxide, benzoyl peroxide, isopropyl percarbonate, or azobisisobutyronitrile, or photoinitiators such as aromatic α-hydroxyketones, alkoxybenzoin, acetophenone, tert-butylperoxine decanoate, acylphosphine oxide, tertiary amines, diketones, or mixtures thereof. Examples of photoinitiators include 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide (DMBAPO), bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide (Irgacure819), 2,4,6-trimethylbenzyldiphenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, benzoin methyl ester, camphorquinone, and ethyl 4-(N,N-dimethylamino)benzoate. Photoinitiators may be used individually or in combination. Examples of commercially available visible light photoinitiators include Irgacure 819, Irgacure 1700, Irgacure 1800, Irgacure 819, Irgacure 1850 (manufactured by Ciba Specialty Chemicals), and Lucilin TPO initiator, but are not limited to these, and may include at least one of these materials.

[0064] In one embodiment, the silicone hydrogel contact lens forming composition may contain about 1 to about 38 parts by weight of an initiator per 100 parts by weight of silicon-containing macromer.

[0065] In one embodiment, the silicone hydrogel contact lens forming composition may further contain substances known as additives that can be added to compositions for manufacturing contact lenses, such as UV blockers, pigments, antioxidants, plasticizers, wetting agents, lubricants, viscosity reducers, compatibility enhancers, and the like.

[0066] The silicone hydrogel contact lens forming composition allows for the production of silicone hydrogel contact lenses using generally known contact lens manufacturing methods. For example, the silicone hydrogel contact lens forming composition obtained by mixing as described in detail above is poured into a mold, polymerized using heat, ultraviolet light, infrared light, etc. to form a lens, the dried lens is removed from the mold, and a hydration treatment is performed. This completes the manufacturing of the silicone hydrogel contact lens.

[0067] Silicone hydrogel contact lenses manufactured using the above-mentioned silicone hydrogel contact lens forming composition exhibit physical properties that simultaneously satisfy high oxygen permeability and high water content.

[0068] In one embodiment, the silicone hydrogel contact lens has a water content of about 50% to about 60% and an oxygen permeability (Dk) of about 80 to about 120.

[0069] As described above, in order to achieve the desired physical properties of the manufactured contact lenses, it is necessary to appropriately formulate the silicone hydrogel contact lens forming composition. As a result, silicone hydrogel contact lenses can be obtained that have improved durability such as strength, elongation, and Young's modulus, as well as improved water content and oxygen permeability.

[0070] In one embodiment, the silicone hydrogel contact lens has a load of approximately 6 kgf / mm². 2 ~approximately 8 kgf / mm² 2 It has tensile strength. In one embodiment, the silicone hydrogel contact lens has an elongation of about 150% to about 200%. In one embodiment, the silicone hydrogel contact lens has an elongation of about 0.3 kgf / mm 2 ~Approximately 0.8 kgf / mm 2 It has a tensile modulus of elasticity. In one embodiment, the silicone hydrogel contact lens is approximately 80 × 10 -11 (cm 2 / s)[mlO2 / (ml·mmHg)]~Approx. 115×10 -11 (cm2 It has an oxygen permeability of [mlO2 / (ml·mmHg)]. In one embodiment, the silicone hydrogel contact lens has a water content of about 50% to about 55%.

[0071] In some embodiments, various lens compositions prepared according to the description herein are provided, examples of such compositions include: (1) a composition comprising about 100 parts by weight of silicon-containing macromer of chemical formula 11, about 95 parts by weight of PEG200, about 162 parts by weight of hydrophilic monomer, about 108 parts by weight of silicon-containing monomer, about 5 parts by weight of crosslinking agent, and about 5 parts by weight of initiator; (2) a composition comprising about 38 parts by weight of silicon-containing macromer of chemical formula 11, about 62 parts by weight of silicon-containing macromer of chemical formula 12, about 83 parts by weight of PEG200, about 135 parts by weight of hydrophilic monomer, about 90 parts by weight of silicon-containing monomer, about 4 parts by weight of crosslinking agent, initiator (3) A composition comprising approximately 4 parts by weight of a crosslinking agent, (4) A composition comprising approximately 100 parts by weight of a silicon-containing macromer of chemical formula 13, approximately 83 parts by weight of PEG200, approximately 135 parts by weight of a hydrophilic monomer, approximately 90 parts by weight of a silicon-containing monomer, approximately 4 parts by weight of a crosslinking agent, and approximately 4 parts by weight of an initiator, (5) A composition comprising approximately 97 parts by weight of a silicon-containing macromer of chemical formula 11, approximately 3 parts by weight of a silicon-containing macromer of chemical formula 12, approximately 6 parts by weight of PEG400, approximately 114 parts by weight of a hydrophilic monomer, approximately 76 parts by weight of a silicon-containing monomer, approximately 4 parts by weight of a crosslinking agent, and approximately 4 parts by weight of an initiator, (6) A composition comprising approximately 3 parts by weight of a silicon-containing macromer of chemical formula 12, and chemical formula 13 (6) A composition comprising approximately 97 parts by weight of silicon-containing macromer of chemical formula 13, approximately 6 parts by weight of PEG400, approximately 114 parts by weight of hydrophilic monomer, approximately 76 parts by weight of silicon-containing monomer, approximately 4 parts by weight of crosslinking agent, and approximately 4 parts by weight of initiator; (7) A composition comprising approximately 100 parts by weight of silicon-containing macromer of chemical formula 13, approximately 6 parts by weight of PEG400, approximately 114 parts by weight of hydrophilic monomer, approximately 76 parts by weight of silicon-containing monomer, approximately 4 parts by weight of crosslinking agent, and approximately 4 parts by weight of initiator; (8) A composition comprising approximately 100 parts by weight of silicon-containing macromer of chemical formula 14, approximately 28 parts by weight of PEG400, approximately 87 parts by weight of hydrophilic monomer, approximately 58 parts by weight of silicon-containing monomer, and approximately 3 parts by weight of crosslinking agent (8) A composition comprising parts by weight of a silicon-containing macromer of chemical formula 11, about 78 parts by weight of a silicon-containing macromer of chemical formula 15, about 28 parts by weight of PEG400, about 87 parts by weight of a hydrophilic monomer, about 58 parts by weight of a silicon-containing monomer, about 3 parts by weight of a crosslinking agent, and about 3 parts by weight of an initiator. (9) A composition comprising about 25 parts by weight of a silicon-containing macromer of chemical formula 14, about 75 parts by weight of a silicon-containing macromer of chemical formula 16, about 95 parts by weight of PEG400, about 162 parts by weight of a hydrophilic monomer, about 108 parts by weight of a silicon-containing monomer, about 5 parts by weight of a crosslinking agent, and about 5 parts by weight of an initiator.(10) A composition comprising approximately 25 parts by weight of silicon-containing macromer of chemical formula 14, approximately 75 parts by weight of silicon-containing macromer of chemical formula 17, approximately 83 parts by weight of PEG1000, approximately 135 parts by weight of hydrophilic monomer, approximately 90 parts by weight of silicon-containing monomer, approximately 4 parts by weight of crosslinking agent, and approximately 4 parts by weight of initiator; (11) A composition comprising approximately 3 parts by weight of silicon-containing macromer of chemical formula 15, approximately 97 parts by weight of silicon-containing macromer of chemical formula 18, approximately 95 parts by weight of PEG1000, approximately 162 parts by weight of hydrophilic monomer, approximately 108 parts by weight of silicon-containing monomer, approximately 5 parts by weight of crosslinking agent, and approximately 5 parts by weight of initiator; (12) A composition comprising approximately 25 parts by weight of silicon-containing macromer of chemical formula 14 (13) A composition comprising approximately 97 parts by weight of silicon-containing macromer, approximately 3 parts by weight of silicon-containing macromer of chemical formula 19, approximately 95 parts by weight of PEG1000, approximately 162 parts by weight of hydrophilic monomer, approximately 108 parts by weight of silicon-containing monomer, approximately 5 parts by weight of crosslinking agent, and approximately 5 parts by weight of initiator; and (13) a composition comprising approximately 62 parts by weight of silicon-containing macromer of chemical formula 18, approximately 38 parts by weight of silicon-containing macromer of formula 20, approximately 95 parts by weight of PEG1000, approximately 162 parts by weight of hydrophilic monomer, approximately 108 parts by weight of silicon-containing monomer, approximately 5 parts by weight of crosslinking agent, and approximately 5 parts by weight of initiator. Examples include, but are not limited to, this. In various embodiments, the hydrophilic monomer is N-vinyl-2-pyrrolidone (NVP), the crosslinking agent is tri(ethylene glycol) dimethacrylate (TEGDMA), the silicon-containing monomer is α,ω-bismethacryloxypropyl polydimethylsiloxane (SiGMA), and the initiator is 2,2'-azobisisobutyronitrile (AIBN).

[0072] Examples and comparative examples of the present disclosure are described below. The following examples are merely embodiments of the present disclosure and are not intended to limit the present disclosure. [Examples]

[0073] [Example 1] The compound is composed of 100 parts by weight of the compound represented by the following chemical formula 11 as a silicon-containing macromer (weight-average molecular weight 1000 Da), 162 parts by weight of N-vinyl-2-pyrrolidone (NVP) as a hydrophilic monomer, 95 parts by weight of polyethylene glycol (weight-average molecular weight 200 Da), 5 parts by weight of tri(ethylene glycol) dimethacrylate (TEGDMA) as a crosslinking agent, α,ω-bismethacryloxypropyl polydimethylsiloxane (SiGMA) as a silicon-containing monomer, and 2,2'-azobisisobutyro Nitrile (AIBN) was added to complete the preparation of the silicone hydrogel contact lens forming composition. A silicone hydrogel contact lens forming composition was injected into a polypropylene mold and polymerized at 110°C to produce a lens. After drying the lens, it was separated from the mold. The separated lens was then hydrated with physiological saline and sterilized at 120°C to complete the manufacturing of the silicone hydrogel contact lens.

[0074] [ka] In chemical formula 11, R1 to R4 are methyl groups, R5 is a butyl group, a=1, b=1, and c=15.

[0075] [Example 2] The compound represented by chemical formula 11 and the compound represented by chemical formula 12 were mixed in the amounts shown in Table 1 below to obtain 100 parts by weight of silicon macromer. 135 parts by weight of NVP as a hydrophilic monomer, 83 parts by weight of polyethylene glycol (weight-average molecular weight 200 Da), 4 parts by weight of TEGDMA as a crosslinking agent, SiGMA as a silicon-containing monomer, and AIBN as a thermal initiator were added to complete the production of the silicone hydrogel contact lens. Subsequently, a silicone hydrogel contact lens was produced in the same manner as in Example 1.

[0076] [ka] In chemical formula 12, R1 to R4 are methyl groups, a=1, and b=9.

[0077] [Example 3] Using the compound represented by the following chemical formula 13, 100 parts by weight of silicon-containing macromer were prepared. 135 parts by weight of NVP as a hydrophilic monomer, 83 parts by weight of polyethylene glycol (weight-average molecular weight 200 Da), 4 parts by weight of TEGDMA as a crosslinking agent, SiGMA as a silicon-containing monomer, and AIBN as a thermal initiator were mixed to complete the preparation of a composition for forming a silicone hydrogel contact lens. Subsequently, a silicone hydrogel contact lens was manufactured in the same manner as in Example 1.

[0078] [ka] In chemical formula 13, R1 to R4 are methyl groups, R5 is a butyl group, a=3, and b=6.

[0079] [Example 4] The compound represented by chemical formula 11 and the compound represented by chemical formula 12 were mixed in the amounts shown in Table 1 below to obtain 100 parts by weight of silicon macromer. Then, 114 parts by weight of NVP as a hydrophilic monomer, 6 parts by weight of polyethylene glycol (weight-average molecular weight 400 Da), 4 parts by weight of TEGDMA as a crosslinking agent, SiGMA as a silicon-containing monomer, and AIBN as a thermal initiator were mixed to complete the preparation of the composition for forming a silicone hydrogel contact lens. Subsequently, a silicone hydrogel contact lens was manufactured in the same manner as in Example 1.

[0080] [Example 5] The compound represented by chemical formula 12 and the compound represented by chemical formula 13 were mixed in the amounts shown in Table 1 below to obtain 100 parts by weight of silicon macromer. 114 parts by weight of NVP as a hydrophilic monomer, 6 parts by weight of polyethylene glycol (weight-average molecular weight 400 Da), 4 parts by weight of TEGDMA as a crosslinking agent, SiGMA as a silicon-containing monomer, and AIBN as a thermal initiator were added to complete the preparation of the composition for forming silicone hydrogel contact lenses. Subsequently, silicone hydrogel contact lenses were manufactured in the same manner as in Example 1.

[0081] [Example 6] Using the compound represented by chemical formula 13, a silicon-containing macromer was prepared to amount to 100 parts by weight. 114 parts by weight of NVP as a hydrophilic monomer, 6 parts by weight of polyethylene glycol (weight-average molecular weight 400 Da), 4 parts by weight of TEGDMA as a crosslinking agent, SiGMA as a silicon-containing monomer, and AIBN as a thermal initiator were mixed to complete the preparation of a composition for forming a silicone hydrogel contact lens. Subsequently, a silicone hydrogel contact lens was manufactured in the same manner as in Example 1.

[0082] [Example 7] Using the compound represented by the following chemical formula 14, 100 parts by weight of silicon-containing macromer were prepared. 87 parts by weight of NVP as a hydrophilic monomer, 28 parts by weight of polyethylene glycol (weight-average molecular weight 200 Da), 3 parts by weight of TEGDMA as a crosslinking agent, SiGMA as a silicon-containing monomer, and AIBN as a thermal initiator were mixed to complete the preparation of a composition for forming a silicone hydrogel contact lens. Subsequently, a silicone hydrogel contact lens was manufactured in the same manner as in Example 1.

[0083] [ka] In chemical formula 14, R1 to R4 are methyl groups, R5 is a hydroxyl-substituted butyl group, a=6, and b=18.

[0084] [Example 8] The compound represented by chemical formula 11 and the compound represented by chemical formula 15 were mixed in the amounts shown in Table 1 below to obtain 100 parts by weight of silicon macromer. 87 parts by weight of NVP as a hydrophilic monomer, 28 parts by weight of polyethylene glycol (weight-average molecular weight 400 Da), 3 parts by weight of TEGDMA as a crosslinking agent, SiGMA as a silicon-containing monomer, and AIBN as a thermal initiator were added to complete the preparation of the composition for forming silicone hydrogel contact lenses. Subsequently, silicone hydrogel contact lenses were manufactured in the same manner as in Example 1.

[0085] [ka] In chemical formula 15, R1 to R4 are methyl groups, a=1, and b=9.

[0086] [Example 9] The compound represented by chemical formula 14 and the compound represented by chemical formula 16 were mixed in the amounts shown in Table 1 below to obtain 100 parts by weight of silicon macromer. Then, 162 parts by weight of NVP as a hydrophilic monomer, 95 parts by weight of polyethylene glycol (weight-average molecular weight 400 Da), 5 parts by weight of TEGDMA as a crosslinking agent, SiGMA as a silicon-containing monomer, and AIBN as a thermal initiator were mixed to complete the preparation of the composition for forming silicone hydrogel contact lenses. Subsequently, silicone hydrogel contact lenses were manufactured in the same manner as in Example 1.

[0087] [ka] In chemical formula 16, R1 and R2 are methyl groups, R4 and R3 are methyl groups substituted with amines, a=3, and b=13.

[0088] [Example 10] The compound represented by chemical formula 14 and the compound represented by chemical formula 17 were mixed in the amounts shown in Table 1 below to obtain 100 parts by weight of silicon macromer. Then, 135 parts by weight of NVP as a hydrophilic monomer, 83 parts by weight of polyethylene glycol (weight-average molecular weight 1000 Da), 4 parts by weight of TEGDMA as a crosslinking agent, SiGMA as a silicon-containing monomer, and AIBN as a thermal initiator were mixed to complete the preparation of the composition for forming silicone hydrogel contact lenses. Subsequently, silicone hydrogel contact lenses were manufactured in the same manner as in Example 1.

[0089] [ka] In chemical formula 17, R1 to R4 are methyl groups, R5 is a hexyl group substituted with hydroxyl, a=6, b=6, and c=20.

[0090] [Example 11] The compound represented by chemical formula 15 and the compound represented by chemical formula 18 were mixed in the amounts shown in Table 1 below to obtain 100 parts by weight of silicon macromer. Then, 162 parts by weight of NVP as a hydrophilic monomer, 95 parts by weight of polyethylene glycol (weight-average molecular weight 1000 Da), 5 parts by weight of TEGDMA as a crosslinking agent, SiGMA as a silicon-containing monomer, and AIBN as a thermal initiator were mixed to complete the preparation of the composition for forming silicone hydrogel contact lenses. Subsequently, silicone hydrogel contact lenses were manufactured in the same manner as in Example 1.

[0091] [ka] In chemical formula 18, R1 to R4 are methyl groups, R5 is a hexyl group substituted with an amide, a=6, b=6, and c=18.

[0092] [Example 12] The compound represented by chemical formula 18 and the compound represented by chemical formula 19 were mixed in the amounts shown in Table 1 below to obtain 100 parts by weight of silicon macromer. 162 parts by weight of NVP as a hydrophilic monomer, 95 parts by weight of polyethylene glycol (weight-average molecular weight 1000 Da), 4 parts by weight of TEGDMA as a crosslinking agent, SiGMA as a silicon-containing monomer, and AIBN as a thermal initiator were added to complete the preparation of the composition for forming silicone hydrogel contact lenses. Subsequently, silicone hydrogel contact lenses were manufactured in the same manner as in Example 1.

[0093] [ka] In chemical formula 19, R1 to R3 are propyl groups, R4 is a methyl group substituted with a hydroxyl group, a=6, and b=13.

[0094] [Example 13] The compound represented by chemical formula 18 and the compound represented by chemical formula 20 were mixed in the amounts shown in Table 1 below to obtain 100 parts by weight of silicon macromer. Then, 162 parts by weight of NVP as a hydrophilic monomer, 95 parts by weight of polyethylene glycol (weight-average molecular weight 1000 Da), 4 parts by weight of TEGDMA as a crosslinking agent, SiGMA as a silicon-containing monomer, and AIBN as a thermal initiator were mixed to complete the preparation of the composition for forming silicone hydrogel contact lenses. Subsequently, silicone hydrogel contact lenses were manufactured in the same manner as in Example 1.

[0095] [ka] In chemical formula 20, R1 to R3 are propyl groups, R4 is a methyl group substituted with hydroxyl, a=3, and b=13.

[0096] [Comparative Example 1] Using the compound represented by chemical formula 13, a silicon-containing macromer was prepared to amount to 100 parts by weight. 114 parts by weight of NVP as a hydrophilic monomer, 6 parts by weight of polyethylene glycol (weight-average molecular weight 200 Da), 4 parts by weight of TEGDMA as a crosslinking agent, SiGMA as a silicon-containing monomer, and AIBN as a thermal initiator were mixed to complete the preparation of a composition for forming a silicone hydrogel contact lens. Subsequently, a silicone hydrogel contact lens was manufactured in the same manner as in Example 1.

[0097] [Comparative Example 2] The compound represented by chemical formula 12 and the compound represented by chemical formula 13 were mixed in the amounts shown in Table 2 below to obtain 100 parts by weight of silicon macromer. Then, 212 parts by weight of NVP as a hydrophilic monomer, 10 parts by weight of polyethylene glycol (weight-average molecular weight 400 Da), 7 parts by weight of TEGDMA as a crosslinking agent, SiGMA as a silicon-containing monomer, and AIBN as a thermal initiator were mixed to complete the preparation of the composition for forming a silicone hydrogel contact lens. Subsequently, a silicone hydrogel contact lens was manufactured in the same manner as in Example 1.

[0098] [Comparative Example 3] Using the compound represented by chemical formula 11, a silicon-containing macromer was prepared to a concentration of 100 parts by weight. 212 parts by weight of NVP as a hydrophilic monomer, 10 parts by weight of polyethylene glycol (weight-average molecular weight 400 Da), 7 parts by weight of TEGDMA as a crosslinking agent, SiGMA as a silicon-containing monomer, and AIBN as a thermal initiator were mixed to complete the preparation of a composition for forming a silicone hydrogel contact lens. Subsequently, a silicone hydrogel contact lens was manufactured in the same manner as in Example 1.

[0099] [Comparative Example 4] Using the compound represented by chemical formula 12, a silicon-containing macromer was prepared to amount to 100 parts by weight. 45 parts by weight of NVP as a hydrophilic monomer, 44 parts by weight of polyethylene glycol (weight-average molecular weight 1000 Da), 1 part by weight of TEGDMA as a crosslinking agent, SiGMA as a silicon-containing monomer, and AIBN as a thermal initiator were mixed to complete the preparation of a composition for forming a silicone hydrogel contact lens. Subsequently, a silicone hydrogel contact lens was manufactured in the same manner as in Example 1.

[0100] [Comparative Example 5] Using the compound represented by chemical formula 17, a silicon-containing macromer was prepared to amount to 100 parts by weight. 45 parts by weight of NVP as a hydrophilic monomer, 44 parts by weight of polyethylene glycol (weight-average molecular weight 1000 Da), 1 part by weight of TEGDMA as a crosslinking agent, SiGMA as a silicon-containing monomer, and AIBN as a thermal initiator were mixed to complete the preparation of a composition for forming a silicone hydrogel contact lens. Subsequently, a silicone hydrogel contact lens was manufactured in the same manner as in Example 1.

[0101] [Comparative Example 6] The compound represented by chemical formula 14 and the compound represented by chemical formula 19 were mixed in the amounts shown in Table 2 below to obtain 100 parts by weight of silicon macromer. Then, 45 parts by weight of NVP as a hydrophilic monomer, 44 parts by weight of polyethylene glycol (weight-average molecular weight 1000 Da), 1 part by weight of TEGDMA as a crosslinking agent, SiGMA as a silicon-containing monomer, and AIBN as a thermal initiator were mixed to complete the preparation of the composition for forming a silicone hydrogel contact lens. Subsequently, a silicone hydrogel contact lens was manufactured in the same manner as in Example 1.

[0102] The formulations of the silicone hydrogel contact lens forming compositions produced according to Examples 1-13 and Comparative Examples 1-6 are shown in Tables 1 and 2 below.

[0103] [Table 1]

[0104] [Table 2]

[0105] [Evaluation Example 1] The dispersion force (δD), dipole attraction force (δP), and hydrogen bonding force (δH) of the silicon-containing macromer and polyethylene glycol in each composition of Examples 1-13 and Comparative Examples 1-6 were determined using the Y-BM Group Contribution method, and their differences ΔδD, ΔδP, and ΔδH were evaluated and are shown in Table 3 below.

[0106] [Table 3] TIFF0007857303000018.tif217153

[0107] [Evaluation Example 2] The physical properties of each silicone hydrogel contact lens manufactured according to Examples 1-13 and Comparative Examples 1-6 were evaluated by the following method and are shown in Table 4.

[0108] (Evaluation of strength, elongation, and Young's modulus) Tensile testing fixtures are attached to both ends of a test specimen conforming to the ASTM standard. After attachment, a load is applied to the fixture at a constant speed, and the mechanical properties of the specimen are measured from the deformation that appears in the specimen. Depending on the characteristics of each test specimen, deformation or fracture occurs in response to the applied force, which is called tensile strain and tensile stress, respectively. The property of returning to the original shape after deformation when a load is applied and then removed is called elasticity. The slope of the elastic region can be expressed by Young's modulus. Elongation is defined as ε = ΔL / L0, which is the ratio of the change ΔL (change in the length of the test specimen in response to the applied force) to the original gauge length L0 (initial length of the test specimen before force is applied), and is generally expressed as a percentage.

[0109] (water content) The water content of each lens is measured by gravimetric method. The moisture is removed from the surface of the lens, and its weight is measured. The weight is measured after drying at 100°C to 110°C (60°C ± 5°C if the lens material has been changed) until there is no further weight change. Lenses weighing 100mg to 300mg are used, and their weight is measured to the nearest 0.1mg. Water content (W H20 The result is calculated as a percentage using the following formula.

number

[0110] (Oxygen permeability) The oxygen permeability (Dk) of a lens is expressed by the diffusion coefficient (D), which is the ability of oxygen to pass through the material, and the solubility coefficient (k), which indicates the degree to which oxygen dissolves in the material. In this invention, oxygen permeability was measured by polarography in accordance with ISO 18369.

[0111] [Table 4]

[0112] As can be seen from the results shown in Tables 3 and 4, the silicone hydrogel contact lenses of Examples 1 to 13, which satisfy all the conditions for determining the Hansen solubility parameter, were confirmed to have an oxygen permeability (Dk) of 80 to 120 and an oxygen content of 50% to 60%. In other words, they meet all the predetermined standards. Furthermore, the silicone hydrogel contact lenses of Examples 1 to 13 were confirmed to have good durability evaluation results in terms of strength, elongation, and Young's modulus.

[0113] As is clear from the above explanation, the silicone hydrogel contact lenses according to this disclosure exhibit high oxygen permeability and high water content compared to the comparative examples. Below, we will explain the specific details of implementing this disclosure, and in addition to the effects mentioned above, we will describe the specific effects of this disclosure. Although the present disclosure has been described above with reference to embodiments, the present disclosure is not limited to these embodiments, and those skilled in the art will understand that various modifications can be made without departing from the technical idea of ​​the present disclosure. Furthermore, although the effects of the configurations of the present disclosure are not explicitly described in the detailed description of the embodiments above, the predictable effects of the corresponding configurations should also be recognized.

Claims

1. A method for manufacturing a silicone hydrogel contact lens having an oxygen permeability of 80 × 10⁻¹¹ (cm² / s) [mlO₂ / (ml·mmHg)] to 120 × 10⁻¹¹ (cm² / s) [mlO₂ / (ml·mmHg)] and a water content of 50% to 60%, 10-40% by weight of silicon-containing macromers, A polyethylene glycol having a molecular weight of 200 to 1,000 g / mol in 1 to 20% by weight, The process involves polymerizing a silicone hydrogel contact lens forming composition containing a crosslinking agent and an initiator. In the composition, the difference ΔδD, ΔδP, and ΔδH of the dispersion force (δD), dipole attraction force (δP), and hydrogen bonding force (δH) that determine the Hansen solubility parameter of the silicon-containing macromer and the polyethylene glycol, respectively, satisfies the following conditions: -6.0MPa 1 / 2 ≦△δD≦1.0MPa 1 / 2 1.5MPa 1 / 2 ≦△δP≦3.5MPa 1 / 2 4.0MPa 1 / 2 ≦△δH≦8.0MPa 1 / 2 A method for producing silicone hydrogel contact lenses, wherein the polymerization is carried out in a manner in which at least 95% of the polyethylene glycol is removed from the composition by thermal polymerization at a temperature of 100°C to 110°C or by UV light polymerization.

2. A method for producing a silicone hydrogel contact lens according to claim 1, wherein the polyethylene glycol is PEG200, PEG400, or PEG1000.

3. The method for producing a silicone hydrogel contact lens according to claim 1, wherein the silicon-containing macromer contains a siloxane chain and has one or two acrylic functional groups.

4. The method for producing a silicone hydrogel contact lens according to claim 1, wherein the silicon-containing macromer has a weight-average molecular weight of 500 Da to 2,500 Da.

5. The method for producing a silicone hydrogel contact lens according to claim 1, wherein the silicone hydrogel contact lens forming composition further comprises a hydrophilic monomer.

6. The method for producing a silicone hydrogel contact lens according to claim 5, wherein the hydrophilic monomer is at least one selected from N,N-dimethylacrylamide, 2-hydroxyethyl methacrylate, glycerol monomethacrylate, 2-hydroxyethyl methacrylate, polyethylene glycol monomethacrylate, methacrylic acid, acrylic acid, N-vinylpyrrolidone, N-vinyl-N-methylacetamide, N-vinyl-N-ethylacetamide, N-vinyl-N-ethylformamide, N-vinylformamide, and combinations thereof.

7. The method for producing a silicone hydrogel contact lens according to claim 5, wherein the composition for forming the silicone hydrogel contact lens contains 20 to 239 parts by weight of the hydrophilic monomer per 100 parts by weight of the silicon macromer.

8. The method for producing a silicone hydrogel contact lens according to claim 5, wherein the silicone hydrogel contact lens forming composition contains 10 to 50% by weight of the hydrophilic monomer.

9. The method for producing a silicone hydrogel contact lens according to claim 1, wherein the silicone hydrogel contact lens forming composition further comprises a silicon monomer.

10. The method for producing a silicone hydrogel contact lens according to claim 9, wherein the silicon-containing monomer is at least one selected from α,ω-bismethacryloxypropyl polydimethylsiloxane (SiGMA), 3-methacryloxypropyl tris(trimethylsiloxy)silane (TRIS), monomethacryloxypropyl-terminated polydimethylsiloxane, polydimethylsiloxane, 3-methacryloxypropyl bis(trimethylsiloxy)methylsilane, methacryloxypropyl pentamethyldisiloxane, or combinations thereof.

11. The method for producing a silicone hydrogel contact lens according to claim 9, wherein the silicone hydrogel contact lens forming composition contains 10 to 20% by weight of the silicon-containing monomer.

12. The method for producing a silicone hydrogel contact lens according to claim 1, wherein the crosslinking agent comprises at least one selected from allyl methacrylate (AMA), divinylbenzene (DVB), triethylene glycol dimethacrylate (TrEGDMA), triallyl isocyanurate (TAIC), ethylene glycol dimethyl acrylate (EGDMA), ethylenediamine dimethacrylamide, glycerol dimethacrylate, and combinations thereof.

13. The initiators include lauryl peroxide, benzoyl peroxide, isopropyl percarbonate, azobisisobutyronitrile, aromatic α-hydroxyketone, alkoxybenzoin, acetophenone, tert-butylperoxine decanoate, acylphosphine oxide, tertiary amine, diketone, 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide (DMBAPO), and bis(2,4,6-trimethylbenzoyl). A method for producing a silicone hydrogel contact lens according to claim 1, comprising at least one selected from phenylphosphine oxide, 2,4,6-trimethylbenzyldiphenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, benzoin methyl ester, camphorquinone, 4-(N,N-dimethylamino)ethyl benzoate, Irgacure 819, Irgacure 1700, Irgacure 1800, Irgacure 819, Irgacure 1850, Lucilin TPO initiator, and combinations thereof.

14. The method for producing a silicone hydrogel contact lens according to claim 1, wherein the silicone hydrogel contact lens forming composition further comprises at least one selected from a UV blocking agent, a pigment, a diluent, and a combination thereof.

15. The difference between the dispersion force (δD), dipole attractive force (δP), and hydrogen bonding force (δH) that determine the Hansen solubility parameters of the silicon-containing macromer and the polyethylene glycol, ΔδD, ΔδP, and ΔδH, respectively, is: -0.8MPa 1 / 2 ≦△δD≦0.3MPa 1 / 2 、 2.0MPa 1 / 2 ≦△δP≦2.5MPa 1 / 2 、 4.5 MPa 1 / 2 ≦△δH≦5.7MPa 1 / 2 A method for producing a silicone hydrogel contact lens according to claim 1, which satisfies the conditions.

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