Contact lens and method for manufacturing same

Abstract

The present application relates to a contact lens and a method for manufacturing the contact lens. According to the contact lens and the method for manufacturing the contact lens of the present application, the contact lens has a desired moisture content and a low rate of expansion during hydration and thus can have excellent dimensional stability and oxygen permeability.

Description

Contact lenses and methods for manufacturing the same

[0001] The present application relates to a contact lens and a method for manufacturing the contact lens.

[0002] Contact lenses are typically manufactured using a casting process using polypropylene (PP) molds. These contact lenses, formed into a lens shape through this casting process, are formed by polymerizing a silicone-containing composition into a silicone gel, which is then hydrated into a silicone hydrogel. During this process, the silicone gel hydrates into a silicone hydrogel, undergoing expansion. Therefore, the final contact lens specifications, such as the degree, diameter, curvature, and thickness, are determined by the expanded hydrogel. Therefore, the silicone gel must be manufactured using a PP mold, taking this expansion into account.

[0003] Since the expansion of silicone gel into hydrogel must be predicted as a three-dimensional expansion, reducing the error in the predicted value in the actual process has a significant impact on improving productivity. If the specifications of silicone gel and hydrogel deviate from the predicted values, the problem of repeated redesign and remanufacturing occurs. Hydrogels have spaces between their polymer chains, which can contain water. However, it is not easy to ensure uniform expansion in all directions during the hydration process in the silicone gel state. This causes the hydrogel shape to not expand uniformly during the hydration process, resulting in an oval shape. Therefore, to solve this problem, it is necessary to use a contact lens that has excellent moisture content, dimensional stability, and oxygen permeability.

[0004] The object of the present application is to provide a contact lens having excellent dimensional stability and oxygen permeability while having excellent functional properties, and a method for manufacturing the contact lens.

[0005] In order to solve the above problem, the contact lens of the present application comprises a silicone macromer and a non-reactive diluent, and the Hansen solubility index (HSP) of the silicone macromer is 10.0 MPa. 1 / 2 Up to 20.0 MPa 1 / 2 A silicone hydrogel obtained by polymerizing a silicone-containing composition and undergoing a hydration reaction; and a hardware device.

[0006] In addition, the contact lens of the present application comprises a silicone macromer and a non-reactive diluent, and the Hansen solubility index (HSP) of the silicone macromer is 10.0 MPa. 1 / 2 Up to 20.0 MPa 1 / 2 A silicone hydrogel obtained by polymerizing a silicone-containing composition and undergoing a hydration reaction; and an ocular drug.

[0007] In addition, the silicone-containing composition has a dispersion power (δD) of 13.3 MPa. 1 / 2 Up to 15.0 MPa 1 / 2 and the dipole force (δP) is 4.5 MPa. 1 / 2 Up to 6.6 MPa 1 / 2 , and the hydrogen bonding strength (δH) is 6.8 MPa. 1 / 2 Up to 12.0 MPa 1 / 2 It could be.

[0008] Additionally, the silicone-containing composition may have a polymer-solvent interaction coefficient (χ) of 0.30 to 0.99.

[0009] In addition, the silicon-containing composition has a Gibbs free energy change (△G) of -9 × 10 23 -3.5 × 10 22 It could be.

[0010] Additionally, the silicone macromer may be represented by the following chemical formula 1.

[0011] [Chemical Formula 1]

[0012]

[0013] In the above chemical formula 1, n is 5 to 20, R1 is a (meth)acryloyl group, R2 is an alkylene group having 1 to 40 carbon atoms, and the methylene group included in the alkylene group may be substituted with -O-, -N(R9)- or a carbonyl group, R9 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R3 to R6 are each independently hydrogen, a hydroxyl group, an amino group, a carboxyl group, a halogen atom or an alkyl group having 1 to 3 carbon atoms, and the alkyl group may be substituted with a hydroxyl group, an isocyanate group, a halogen atom, a carboxyl group or an alkoxy group having 1 to 8 carbon atoms, R7 is a single bond or an alkylene group having 1 to 30 carbon atoms, and the methylene group included in the alkylene group is -O-, -N(R 10 )- or may be substituted with a carbonyl group, R 10 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and R8 is hydrogen, a hydroxyl group, an isocyanate group, an amino group, a carboxyl group, a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or a (meth)acryloyl group.

[0014] Additionally, the non-reactive diluent may be at least one selected from the group consisting of organic acid solvents, alcohol solvents, hydrocarbon solvents, and ketone solvents.

[0015] Additionally, the non-reactive diluent may be an aliphatic alcohol having 1 to 13 carbon atoms.

[0016] In addition, the non-reactive diluent has a molar volume of 20 cm 3 / mol to 800 cm 3 / mol may be.

[0017] Additionally, the non-reactive diluent may be included in an amount of more than 0 wt% and less than 50 wt%.

[0018] In addition, the silicone-containing composition may further include one or more selected from the group consisting of a silicone monomer, a hydrophilic monomer, a hydrophilic additive, an amphiphilic polymer, a crosslinking agent, an ultraviolet ray blocking agent, and an initiator.

[0019] In addition, the contact lens may include a lens body including the silicone hydrogel and formed to be wearable on the cornea; a protective layer including the silicone hydrogel and laminated on the lens body; and a hardware device inserted between the lens body and the protective layer.

[0020] In addition, the above silicone hydrogel may have an expansion ratio (E) of the following general formula 1 of 9% or less.

[0021] [General Formula 1]

[0022]

[0023] In the above general formula 1, a is the area of ​​the silicone gel before the hydration reaction, and b is the area of ​​the silicone hydrogel after the hydration reaction.

[0024] Additionally, the silicone hydrogel may have a moisture content of 10% or more.

[0025] In addition, the above silicone hydrogel has an oxygen permeability of 60 × 10 -11 (cm 2 / s)[mLO2 / (mL·mmHg)] to 160 × 10 -11 (cm 2 / s)[mLO2 / (mL·mmHg)] may be.

[0026] In addition, the method for manufacturing a contact lens of the present application includes a silicone macromer and a non-reactive diluent, and the Hansen solubility index (HSP) of the silicone macromer is 10.0 MPa. 1 / 2 Up to 20.0 MPa 1 / 2The method comprises the steps of: inserting a hardware device into a silicone-containing composition; polymerizing the silicone-containing composition into which the hardware device is inserted to produce a silicone gel into which the hardware device is inserted; and hydrating the polymerized silicone gel to produce a silicone hydrogel into which the hardware device is inserted.

[0027] In addition, the method for manufacturing a contact lens of the present application includes a silicone macromer and a non-reactive diluent, and the Hansen solubility index (HSP) of the silicone macromer is 10.0 MPa. 1 / 2 Up to 20.0 MPa 1 / 2 The method comprises the steps of mixing an ocular drug into a silicone-containing composition; polymerizing the silicone-containing composition mixed with the ocular drug to produce a silicone gel loaded with the ocular drug; and hydrating the polymerized silicone gel to produce a silicone hydrogel loaded with the ocular drug.

[0028] In addition, in the method for manufacturing the contact lens, the non-reactive diluent included in the silicone gel can be replaced with water through the hydration reaction during the hydration reaction.

[0029] In addition, the method for manufacturing the contact lens includes a silicone macromer and a non-reactive diluent, and the Hansen solubility index (HSP) of the silicone macromer is 10.0 MPa. 1 / 2 Up to 20.0 MPa 1 / 2 A method for producing a silicone hydrogel comprising: polymerizing a silicone-containing composition; and a step of subjecting the polymerized silicone gel to a hydration reaction with an ocular drug solution to produce a silicone hydrogel loaded with an ocular drug.

[0030] In addition, in the method for manufacturing the contact lens, during the hydration reaction, some or all of the non-reactive diluent contained in the silicone gel can be replaced with the ocular drug through the hydration reaction.

[0031] According to the contact lens of the present application and the method for manufacturing the contact lens, the contact lens can have excellent dimensional stability and excellent oxygen permeability while having a desired water content and a low expansion rate generated during the hydration process.

[0032] The present application relates to a silicone-containing composition. The silicone-containing composition comprises a silicone macromer and a non-reactive diluent, wherein the silicone macromer has a Hansen solubility index (HSP) of 10.0 MPa. 1 / 2 Up to 20.0 MPa 1 / 2 Specifically, the Hansen solubility index of the aforementioned silicone macromer is 11.0 MPa 1 / 2 up to 18.0 MPa 1 / 2 or 11.0 MPa 1 / 2 up to 16.0 MPa 1 / 2 It can be. The silicone-containing composition including the above-described components can have a desired water content while having a low expansion rate generated during the hydration process, thereby exhibiting excellent dimensional stability and excellent oxygen permeability, in the process of forming a silicone hydrogel described later through a hydration reaction, by having the Hansen solubility index of the silicone macromer satisfying the above-described range.

[0033] In this specification, the "Hansen Solubility Index (HSP)" refers to an index indicating the solubility to which a substance will dissolve in another substance. The Hansen Solubility Index is a three-dimensional representation of the solubility parameter introduced by Hildebrand, which is divided into three components: dispersion force (δD), dipole attraction (δP), and hydrogen bonding force (δH), which will be described later. The specific definition and calculation of the Hansen Solubility Index are described in the following references.

[0034] Charles M. Hansen, Hansen Solubility Parameters: A Users Handbook (CRC Press, 2007).

[0035] The above dispersion force (δD) reflects the van der Waals force, the above dipole attraction (δP) reflects the dipole moment, and the above hydrogen bonding force (δH) reflects the action of water or alcohol, etc. At this time, the Hansen solubility index (HSP) of the silicone-containing composition is the sum of the three components, and can be calculated by the following general formula 2.

[0036] [General Formula 2]

[0037] HSP= (δD 2 + δP 2 + δH 2 ) 1 / 2

[0038] In the above general formula 2, δD is the dispersion force of the silicon-containing composition, δP is the dipole attraction force of the silicon-containing composition, and δH is the hydrogen bonding force of the silicon-containing composition.

[0039] The above Hansen solubility index (HSP[δD, δP, δH]) can be conveniently estimated from the chemical structure, for example, using the computer software Hansen Solubility Parameters in Practice (HSPiP). Specifically, the Hansen solubility index can be obtained from the chemical structure by the Y-MB method implemented in HSPiP. In addition, the Hansen solubility index can be obtained from the results of dissolution tests using multiple solvents by the sphere method implemented in HSPiP when the chemical structure is unknown. In the present specification, the Hansen solubility index can be determined by the types of silicone macromer and non-reactive diluent used, the content thereof, etc.

[0040] The Hansen solubility index (HSP) of the above silicone-containing composition is 15.5 MPa 1 / 2 Up to 20.7 MPa 1 / 2 , 16.2 MPa 1 / 2 Up to 20.5 MPa 1 / 2 or 16.3 MPa 1 / 2 Up to 20.0 MPa 1 / 2The silicone-containing composition may have a Hansen solubility index satisfying the aforementioned range, thereby having a desired water content and a low expansion rate occurring during the hydration process, thereby exhibiting excellent dimensional stability and excellent oxygen permeability.

[0041] The above silicone-containing composition has a dispersion power (δD) of 13.3 MPa. 1 / 2 Up to 15.0 MPa 1 / 2 and the dipole force (δP) is 4.5 MPa. 1 / 2 Up to 6.6 MPa 1 / 2 , and the hydrogen bonding strength (δH) is 6.8 MPa. 1 / 2 Up to 12.0 MPa 1 / 2 It can be. Specifically, the silicone-containing composition has a dispersion power (δD) of 13.5 MPa. 1 / 2 Up to 14.5 MPa 1 / 2 and the dipole force (δP) is 4.8 MPa. 1 / 2 up to 6.3 MPa 1 / 2 , and the hydrogen bonding strength (δH) is 7.1 MPa. 1 / 2 Up to 11.5 MPa 1 / 2 The silicone-containing composition may have a desired water content while having a low expansion rate generated during the hydration process, thereby exhibiting excellent dimensional stability and excellent oxygen permeability, as the dispersion force, dipole attraction force, and hydrogen bonding force satisfy the above-described ranges.

[0042] In one example, the silicone-containing composition has a polymer-solvent interaction coefficient (χ) of 0.30 to 0.99. Specifically, the silicone-containing composition may have a polymer-solvent interaction coefficient (χ) of 0.34 to 0.98. Since the polymer-solvent interaction coefficient of the silicone-containing composition satisfies the above-described range, in the process of forming a silicone hydrogel described below through a hydration reaction, the silicone-containing composition may have a desired water content while having a low expansion rate generated during the hydration process, thereby exhibiting excellent dimensional stability and excellent oxygen permeability.

[0043] In this specification, the term "polymer-solvent interaction coefficient" refers to a coefficient indicating the affinity between a silicone macromer and a non-reactive diluent included in a silicone-containing composition. The polymer-solvent interaction coefficient (χ) of the silicone-containing composition can be calculated using the following general formula 3.

[0044] [General Formula 3]

[0045]

[0046] In the above general formula 3, R is the gas constant, T is the absolute temperature, v is the molar volume of the non-reactive diluent, Φ1 is the Hansen solubility index of the silicone macromer, and Φ2 is the Hansen solubility index of the non-reactive diluent.

[0047] In another example, the silicone-containing composition has a Gibbs free energy change (△G) of -9 × 10 23 -3.5 × 10 22 It can be, specifically, -8.9 × 10 23 -3.6 × 10 22 or -8.8 × 10 23 -3.7 × 10 22 The silicone-containing composition can improve the morphology of the silicone gel during a polymerization reaction by satisfying the Gibbs free energy change amount within the above-described range, and thus, in the process of forming a silicone hydrogel described later through a hydration reaction, the silicone hydrogel can have a desired water content while having a low expansion rate generated during the hydration process, thereby exhibiting excellent dimensional stability and excellent oxygen permeability.

[0048] In this specification, "Gibbs free energy" refers to the maximum amount of useful energy that can be extracted during a reversible process in a thermodynamic system while maintaining constant temperature and pressure. The change in Gibbs free energy of the silicone-containing composition can be calculated using the following general equation 4 based on the Flory-Huggins solution theory.

[0049] [General Formula 4]

[0050]

[0051] In the above general equation 4, R is the gas constant, T is the absolute temperature, n1 is the number of moles of silicone macromer, n2 is the number of moles of non-reactive diluent, φ1 is the volume fraction of silicone macromer, φ2 is the volume fraction of non-reactive diluent, and χ is the polymer-solvent interaction coefficient.

[0052] The above silicone macromer is a chain that forms the main skeleton of a three-dimensional structure such as a siloxane bond composed of silicon and oxygen, and refers to a large molecular unit that has a functional group at the terminal and can form a copolymer with other monomers to produce a polymer with a wider molecular weight range, and is a main component of a contact lens described below. For example, the silicone macromer may have a molecular weight of 500 g / mol to 2000 g / mol. By having the above-described molecular weight, the silicone macromer can improve the oxygen permeability, moisture content, tensile strength, etc. of the silicone hydrogel described below.

[0053] In order to improve the oxygen permeability of the silicone hydrogel described below and obtain the desired functional content through appropriate crosslinking, a silicone macromer composed of the following chemical formula 1 can be used.

[0054] [Chemical Formula 1]

[0055]

[0056] In the above chemical formula 1, n is 5 to 20, R1 is a (meth)acryloyl group, R2 is an alkylene group having 1 to 40 carbon atoms, and the methylene group included in the alkylene group may be substituted with -O-, -N(R9)- or a carbonyl group, R9 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R3 to R6 are each independently hydrogen, a hydroxyl group, an amino group, a carboxyl group, a halogen atom or an alkyl group having 1 to 3 carbon atoms, and the alkyl group may be substituted with a hydroxyl group, an isocyanate group, a halogen atom, a carboxyl group or an alkoxy group having 1 to 8 carbon atoms, R7 is a single bond or an alkylene group having 1 to 30 carbon atoms, and the methylene group included in the alkylene group is -O-, -N(R 10 )- or may be substituted with a carbonyl group, R 10 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and R8 is hydrogen, a hydroxyl group, an isocyanate group, an amino group, a carboxyl group, a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or a (meth)acryloyl group.

[0057] Additionally, in the above chemical formula 1, n may be 5 to 15, or 5 to 10.

[0058] The above R2 may be an alkylene group having 1 to 30 carbon atoms, or an alkylene group having 1 to 25 carbon atoms.

[0059] The alkyl group of R3 to R6 may be a methyl group or an ethyl group, and may be a methyl group. In addition, the alkoxy group as a substituent of the alkyl group may have 1 to 6 carbon atoms, or may have 1 to 4 carbon atoms.

[0060] The above R7 may be a single bond or an alkylene group having 1 to 20 carbon atoms, or may be a single bond or an alkylene group having 1 to 15 carbon atoms.

[0061] The alkyl group of the above R8 may have 1 to 6 carbon atoms. The alkoxy group of the above R8 may have 1 to 6 carbon atoms or 1 to 4 carbon atoms.

[0062] The above R9 and R 10 Each of them may be an alkyl group having 1 to 4 carbon atoms, and may be a methyl group or an ethyl group.

[0063] The above non-reactive diluent exists between the polymer chains during the polymerization process of the silicone macromer, and substantially does not react with the silicone macromer, specifically, with the components included in the silicone-containing composition, and serves to maintain a space that can be replaced by water during the hydration reaction. Since the non-reactive diluent has no reactive group, it can exist in its original state without reacting with the silicone macromer or the cross-linking agent described below during the polymerization and cross-linking reaction. That is, when the non-reactive diluent polymerizes with the silicone macromer, the silicone macromer is formed into a polymer chain, and as the compatibility between the polymer chain and the non-reactive diluent changes, alcohol molecules gather within the polymer chain at the nanometer level, and phase separation occurs between the polymer chain and the non-reactive diluent, thereby creating a space where water can be replaced. The phase-separated nanometer-sized non-reactive diluent can be extracted through the hydration process, and water can be replaced in its place. The morphology formed by the non-reactive diluent during the polymerization process maintains its shape even after extraction, and furthermore, the non-reactive diluent is replaced with water through a hydration reaction, which can determine the moisture content of the silicone hydrogel. At this time, since the moisture content is achieved by water replacement of the morphology rather than network expansion due to water absorption, the desired moisture content can be achieved. In addition, the silicone hydrogel has a low swelling rate during the hydration process, so it can have excellent dimensional stability and excellent oxygen permeability.

[0064] The above non-reactive diluent is not particularly limited in type as long as it does not react with the components included in the silicone-containing composition, and may be, for example, one or more solvents selected from the group consisting of organic acid solvents, alcohol solvents, hydrocarbon solvents, and ketone solvents.

[0065] As the organic acid solvent, an organic acid solvent having 1 to 16 carbon atoms or 1 to 9 carbon atoms can be used, and specifically, solvents such as formic acid, acetic acid, propionic acid, acrylic acid, propiolic acid, butyric acid, valeric acid, β-hydroxy β-methylbutyric acid, caproic acid, heptanoic acid, caprylic acid, nonanoic acid, etc. can be used.

[0066] As the alcohol solvent, an aliphatic alcohol having 1 to 13 carbon atoms or an aromatic alcohol solvent having 6 to 12 carbon atoms can be used. Specifically, the n-aliphatic alcohol having 1 to 13 carbon atoms may be methanol, ethanol, 1-propanol, 2-propanol, isopropyl alcohol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 1-octanol, 1-nonanol, 1-decanol, 1-undecanol, 1-dodecanol, tripropylene glycol monobutyl ether, ethylene glycol, propylene glycol, or Butoxy ethanol, etc. can be used. In addition, specifically, as the aromatic alcohol having 6 to 12 carbon atoms, benzyl alcohol, methyl benzyl alcohol, or phenethyl alcohol can be used.

[0067] As the hydrocarbon solvent, an aliphatic hydrocarbon solvent having 1 to 20 carbon atoms, an alicyclic hydrocarbon solvent having 3 to 20 carbon atoms, or an aromatic hydrocarbon solvent having 6 to 20 carbon atoms can be used, and examples thereof include benzene or toluene.

[0068] As the above ketone solvent, for example, acetone or methyl ethyl ketone can be used.

[0069] Specifically, the non-reactive diluent may be an alcohol-based solvent and may be an aliphatic alcohol having 1 to 13 carbon atoms. By using the non-reactive diluent, the expansion ratio can be further reduced.

[0070] In one example, the non-reactive diluent has a molar volume of 20 cm 3 / mol to 800 cm 3 / mol. Specifically, the non-reactive diluent has a molar volume of 20 cm 3 / mol to 650 cm 3 / mol, 30 cm 3 / mol to 500 cm 3 / mol, 40 cm 3 / mol to 350 cm 3 / mol or 50 cm 3 / mol to 200 cm 3 / mol. The non-reactive diluent can form the desired morphology by having the molar volume described above, thereby reducing the expansion rate occurring during the hydration process.

[0071] In addition, the non-reactive diluent may be included in the silicone-containing composition in an amount of more than 0 wt% and less than 50 wt%, specifically, may be included in an amount of 2 wt% or more, 3 wt% or more, or 5 wt% or more, and may be included in an amount of 48 wt% or less, 45 wt% or less, 43 wt% or less, or 40 wt% or less. By including the non-reactive diluent in the silicone-containing composition in the aforementioned amount, the desired numerical ranges of the Hansen solubility index, the polymer-solvent interaction coefficient, the Gibbs free energy change, etc. of the silicone-containing composition can be satisfied, and accordingly, in the process of forming a silicone hydrogel described below through a hydration reaction, the silicone hydrogel can have a desired water content while having a low swelling rate generated during the hydration process, thereby having excellent dimensional stability, and can have excellent oxygen permeability.

[0072] In one example, the silicone-containing composition may further include, in addition to the silicone macromer, one or more selected from a silicone monomer, a hydrophilic monomer, a hydrophilic additive, an amphiphilic polymer, a crosslinking agent, a UV blocking agent, and an initiator. Here, the initiator may be at least one of a photoinitiator and a thermal initiator.

[0073] Specifically, the silicone monomer is a monomer having a molecular weight of 200 g / mol to less than 500 g / mol, and may be included in the silicone-containing composition to improve the elongation, strength, and modulus of the contact lens described below. For example, the silicone monomer may include methacryloxypropyl-terminated polydimethylsiloxane; 2-propenoic acid, 2-methyl-,2-hydroxy-3-3-1,3,3,3-tetramethyl-1-(trimethylsilyl)oxydisiloxanyl-propoxypropyl ester; and / or [tris(trimethylsiloxy)silyl]propyl methacrylate.

[0074] In addition, the hydrophilic monomer is a monomer having a molecular weight of 100 g / mol to 800 g / mol, and may be included in the silicone-containing composition to improve hydrophilicity and flexibility. For example, 2-hydroxyethyl (meth)acrylate and / or hydroxybutyl (meth)acrylate may be used as the hydrophilic monomer.

[0075] Additionally, the hydrophilic additive may be included in the silicone-containing composition to increase the wettability and moisture content of the lens. For example, polyvinyl pyrrolidone, N-vinyl pyrrolidone, and / or N,N-dimethylacrylamide may be used as the hydrophilic additive.

[0076] In addition, the type of the amphiphilic polymer is not particularly limited, and any amphiphilic polymer known in the art can be used without limitation.

[0077] Additionally, the crosslinking agent may be included in the silicone-containing composition to enhance strength and elasticity by forming a network structure through linking monomers. For example, the crosslinking agent may include triallyl isocyanurate, tetraethylene glycol di(meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, and / or allyl (meth)acrylate.

[0078] Additionally, the above UV blocking agent may be included in the silicone-containing composition to prevent ultraviolet rays from directly entering our eyes. For example, the above sunscreens include 2-(4-Benzoyl-3-hydroxyphenoxy)ethyl acrylate, 2,4-dihydroxybenzophenone, 2-ethylhexyl-trans-4-methoxy-cinnamate, 2-hydroxy-4-(methacryloyloxy)benzophenone, 2-(2'-Hydroxy-5'-methacryloxyethylphenyl)-2H-benzotriazole, 2-[3-(2Hbenzotriazol-2-yl)-4-hydroxyphenyl]ethyl methacrylate, etc. can be used.

[0079] Additionally, the photoinitiator may be included in the silicone-containing composition to initiate polymerization in response to light. For example, the photoinitiator may be an aromatic alpha-hydroxy ketone, an alkoxyoxybenzoin, an acetophenone, an acyl phosphine oxide, a tertiary amine, and / or a diketone. Specifically, the photoinitiator may be 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentyl phosphine oxide (DMBAPO), bis(2,4,6-trimethylbenzoyl)-phenyl phosphine oxide (Irgacure 819), 2,4,6-trimethylbenzyldiphenyl phosphine oxide, 2,4,6-trimethylbenzyl diphenylphosphine oxide, benzoin methyl ester, and / or a combination of camphorquinone and ethyl 4-(N,N-dimethylamino)benzoate.

[0080] The present application also relates to a silicone hydrogel. The silicone hydrogel relates to a silicone hydrogel obtained from the aforementioned silicone-containing composition. Since the specific details of the silicone-containing composition described below are equally applicable to the silicone-containing composition described above, they will be omitted.

[0081] The silicone hydrogel is obtained by polymerizing and hydrating the silicone-containing composition described above. Specifically, when the silicone-containing composition is polymerized, a polymer chain is formed, and as the compatibility of the polymer chain and the non-reactive diluent changes, alcohol molecules within the polymer chain gather at the nanometer level, causing phase separation, thereby forming a silicone gel in which a space into which water can be substituted is formed. Thereafter, the silicone gel is obtained by extracting the phase-separated nanometer-sized non-reactive diluent through a hydration reaction, and water is substituted in that space. The silicone hydrogel maintains the morphology formed by the non-reactive diluent during the polymerization process even after extraction, and furthermore, the non-reactive diluent is substituted with water through a hydration reaction, thereby having a desired water content while having a low swelling rate generated during the hydration process, thereby exhibiting excellent dimensional stability and excellent oxygen permeability. The term "silicone gel" as used herein refers to a polymer state after polymerization of a silicone-containing composition but before hydration.

[0082] In one example, the silicone hydrogel may have an expansion ratio (E) of the general formula 1 below of 9% or less, and specifically, may be 7% or less, 5% or less, 3% or less, or 1% or less. In terms of the silicone hydrogel having a lower expansion ratio of the general formula 1 below indicating better dimensional stability, the lower limit is not particularly limited.

[0083] [General Formula 1]

[0084]

[0085] In the above general formula 1, a is the area of ​​the silicone gel before the hydration reaction, and b is the area of ​​the silicone hydrogel after the hydration reaction.

[0086] The silicone hydrogel described above may have excellent dimensional stability because the expansion coefficient of the general formula 1 described above is within the aforementioned range. The silicone gel and silicone hydrogel may be polymerized by a mold during the manufacturing process to take the form of a contact lens. Accordingly, the area of ​​the silicone gel and silicone hydrogel may be calculated based on the diameter measured in the polymerized state.

[0087] In addition, the silicone hydrogel may have a moisture content of 10% or more. In terms of the aspect that the higher the moisture content of the silicone hydrogel, the better the moisture content, the upper limit is not particularly limited, but may be, for example, 50% or less, 45% or less, 40% or less, or 35% or less. The silicone hydrogel may have an excellent moisture content because the moisture content is in the aforementioned range.

[0088] In addition, the above silicone hydrogel has an oxygen permeability of 60 × 10 -11 (cm 2 / s)[mLO2 / (mL·mmHg)] to 160 × 10 -11 (cm 2 / s)[mLO2 / (mL·mmHg)], and specifically, 65 × 10 -11 (cm 2 / s)[mLO2 / (mL·mmHg)] to 153 × 10 -11 (cm 2 / s)[mLO2 / (mL·mmHg)] or 70 × 10 -11 (cm 2 / s)[mLO2 / (mL·mmHg)] to 145 × 10 -11 (cm 2 / s)[mLO2 / (mL·mmHg)]. Since the silicone hydrogel has the oxygen permeability described above, when included in the contact lens described below, the amount of oxygen supplied to the cornea of ​​the eye increases, so that the wearing comfort is excellent and the eye can be maintained in a healthy state. The oxygen permeability can be expressed by the diffusion coefficient (D), which is the ability to pass through the silicone hydrogel, and the solubility coefficient (k), which indicates the degree to which oxygen dissolves in the silicone hydrogel, and can be measured using the polarographic method according to ISO 18369.

[0089] The present application also relates to a method for producing a silicone hydrogel. The method for producing a silicone hydrogel relates to the method for producing the aforementioned silicone hydrogel. Since the specific details regarding the silicone hydrogel described below are equally applicable to the silicone hydrogel described above, they will be omitted.

[0090] The method for producing the above silicone hydrogel comprises a polymerization step and a hydration step. According to the method for producing the silicone hydrogel of the present application, a silicone hydrogel having a desired water content and a low swelling rate during the hydration process, excellent dimensional stability, and excellent oxygen permeability can be produced.

[0091] The above polymerization step is a step of manufacturing a silicone gel by polymerizing the aforementioned silicone-containing composition. For example, the silicone-containing composition can be polymerized by a cast molding method, and specifically, at a wavelength of 350 nm to 500 nm, 2 mW / cm 2 40 mW / cm 2 It can be polymerized by irradiating it with ultraviolet rays at a level of .

[0092] The above hydration step is a step of manufacturing a silicone hydrogel by hydrating the silicone gel polymerized in the above polymerization step. For example, the hydration step can be performed by placing the polymerized silicone gel in purified water for 1 to 3 hours, extracting residual monomers, and replacing the non-reactive diluent with water.

[0093] The present application also relates to a contact lens. The contact lens comprises the aforementioned silicone hydrogel. Since the specific details of the contact lens described below are equally applicable to the silicone hydrogel, they will be omitted.

[0094] The above contact lens comprises the aforementioned silicone hydrogel. According to the contact lens of the present application, not only does it have excellent moisture content, but it also has excellent dimensional stability.

[0095] In one example, the contact lens may further include a hardware device inserted therein. Specifically, the contact lens may be useful for inserting a hardware device therein, as it has the aforementioned physical properties. The hardware device is not particularly limited, but may include, for example, a hardware device such as an electronic component.

[0096] The contact lens having the above-described physical properties may be useful for inserting a hardware device therein. Specifically, the contact lens comprising the silicone hydrogel may be manufactured through a hydration step. The silicone-containing composition forming the lens body of the contact lens generally has a property of expanding during the hydration step, whereas the hardware device inserted into the contact lens may have a property of not expanding. In particular, if the expansion rate is not controlled, the expansion rate of the contact lens comprising the silicone hydrogel may be outside the expected range, and the silicone hydrogel may experience irregular expansion or distortion during the hydration step.

[0097] When a hardware device is inserted into the contact lens, the hardware device may be inserted before the hydration step. Specifically, the hardware device may be inserted into the aforementioned silicone-containing composition, polymerized to produce a silicone gel with the hardware device inserted, and then the polymerized silicone gel may be hydrated to produce a silicone hydrogel with the hardware device inserted. At this time, the silicone gel with the hardware device inserted may be called a dry lens, and the silicone hydrogel with the hardware device inserted may be called a wet lens. Therefore, when the silicone composition undergoes a hydration step after the polymerization step with a hardware device such as an electronic device inserted therein, the silicone composition expands and deforms as it becomes a silicone hydrogel, thereby applying an external force to the hardware device inserted therein. At this time, the expansion of the silicone hydrogel, etc., may cause distortion, failure, or deterioration of the hardware device inserted therein. Therefore, the rate of change in the area, size, thickness, shape, and volume of the contact lens before and after hydration must be small so that the defect rate of the contact lens with hardware inserted can be reduced and its performance can be maintained.

[0098] Here, the rate of change in the area, size, thickness, shape, and volume of the contact lens before and after hydration is affected by the expansion rate of the silicone composition, so it is important to control the expansion rate below a certain level.

[0099] For example, the contact lens may include a lens body, a protective layer, and a hardware device. Specifically, the lens body is the body of the contact lens formed to be wearable on the cornea, and may include the aforementioned silicone hydrogel. In addition, the protective layer is a layer laminated on the lens body to protect the hardware device, and may include the aforementioned silicone hydrogel. In addition, the hardware device is a hardware device such as the aforementioned electronic component, and may be inserted between the lens body and the protective layer.

[0100] In one example, the silicone hydrogel may have an expansion ratio (E) of the following general formula 1 of 9% or less.

[0101] [General Formula 1]

[0102]

[0103] In the above general formula 1, a is the area of ​​the silicone gel before the hydration reaction, and b is the area of ​​the silicone hydrogel after the hydration reaction.

[0104] In another example, the contact lens may further include an ocular drug contained within the lens. Specifically, the contact lens, having the aforementioned physical properties, may be useful for containing an ocular drug within the lens. The ocular drug is not particularly limited, but may include, for example, a drug capable of diagnosing and treating ocular diseases.

[0105] This can be applied not only to the embodiment of inserting an ocular drug-carrying device into the contact lens, but also to cases where the material of the contact lens directly carries the drug. That is, if a space for carrying the drug is prepared in advance in a silicone gel state, the drug can be filled into the space, thereby manufacturing an ocular drug-carrying lens without any change in volume or shape.

[0106] In one embodiment, after mixing an ocular drug into the silicone-containing composition, the silicone-containing composition mixed with the ocular drug is polymerized to produce a silicone gel loaded with the ocular drug, and then the polymerized silicone gel is subjected to a hydration reaction, and when the non-reactive diluent is replaced by water during the hydration reaction, a silicone hydrogel loaded with the ocular drug, i.e., a contact lens, can be manufactured. At this time, the silicone gel loaded with the ocular drug may be referred to as a dry lens, and the silicone hydrogel loaded with the ocular drug may be referred to as a wet lens.

[0107] In another embodiment, after polymerizing a silicone-containing composition, the polymerized silicone gel is subjected to a hydration reaction with an ocular drug solution containing water and an ocular drug, and during the hydration reaction, part or all of the non-reactive diluent is replaced by the ocular drug contained in the ocular drug solution, thereby producing the ocular drug-loaded lens.

[0108] For example, the contact lens may include a lens body, a protective layer, and an ocular drug. Specifically, the lens body is a body of the contact lens formed to be wearable on the cornea, and may include the aforementioned silicone hydrogel. In addition, the protective layer is a layer laminated on the lens body to protect the ocular drug, and may include the aforementioned silicone hydrogel. In addition, the ocular drug may be the aforementioned ocular drug, and may be inserted between the lens body and the protective layer.

[0109]

[0110] Hereinafter, the present application will be described in more detail through examples of the present application, but the scope of the present application is not limited by the examples presented below.

[0111]

[0112] Evaluation method 1. Evaluation of Hansen solubility index (HSP), dispersion power (δD), dipole attraction (δP), and hydrogen bonding strength (δH)

[0113] The Hansen solubility index (HSP) of the silicone macromer used in each example was obtained by the Y-MB method mounted on HSPiP, and the dispersion power (δD), dipole attraction (δP), and hydrogen bonding force (δH) of each silicone-containing composition used in the production of the silicone gel in each example were obtained by the sphere method mounted on HSPiP, and then the Hansen solubility index (HSP) of the silicone-containing composition was calculated and evaluated according to the following general formula 2.

[0114] [General Formula 2]

[0115] HSP= (δD 2 + δP 2 + δH 2 ) 1 / 2

[0116] In the above general formula 2, δD is the dispersion force of the silicon-containing composition, δP is the dipole attraction force of the silicon-containing composition, and δH is the hydrogen bonding force of the silicon-containing composition.

[0117]

[0118] Evaluation Method 2. Evaluation of Polymer-Solvent Interaction Coefficient (χ)

[0119] In each example, the polymer-solvent interaction coefficient (χ) between the silicone macromer and the non-reactive diluent included in each silicone-containing composition used in the production of the silicone gel was calculated and evaluated according to the following general formula 3.

[0120] [General Formula 3]

[0121]

[0122] In the above general formula 3, R is the gas constant, T is the absolute temperature, v is the molar volume of the non-reactive diluent, Φ1 is the Hansen solubility index of the silicone macromer, and Φ2 is the Hansen solubility index of the non-reactive diluent.

[0123]

[0124] Evaluation Method 3. Evaluation of Gibbs-Free Energy Change (△G)

[0125] In each example, the change in Gibbs free energy of each silicone-containing composition used in the manufacture of the silicone gel was calculated and evaluated according to the following general formula 4.

[0126] [General Formula 4]

[0127] )

[0128] In the above general equation 4, R is the gas constant, T is the absolute temperature, n1 is the number of moles of silicone macromer, n2 is the number of moles of non-reactive diluent, φ1 is the Hansen solubility index of silicone macromer, φ2 is the Hansen solubility index of non-reactive diluent, and χ is the polymer-solvent interaction coefficient.

[0129]

[0130] Evaluation Method 4. Expansion Rate (E) Evaluation

[0131] The area of ​​each silicone gel and silicone hydrogel manufactured in each example was measured, and the expansion ratio (E) of the silicone hydrogel was calculated and evaluated according to the following general formula 1.

[0132] [General Formula 1]

[0133]

[0134] In the above general formula 1, a is the area of ​​the silicone gel before the hydration reaction, and b is the area of ​​the silicone hydrogel after the hydration reaction.

[0135]

[0136] Evaluation method 5. Function rate (W H20 )evaluation

[0137] The water content (W) of the silicone hydrogels manufactured in each example H20 ) was evaluated by calculating according to the following general formula 5 using a gravimetric method. At this time, the weight of each silicone hydrogel was measured after removing moisture from the surface, and the weight was measured after drying at 105°C until there was no change in weight.

[0138] [General Formula 5]

[0139]

[0140] In the above general formula 5, m1 is the weight of the silicone hydrogel before drying, and m2 is the weight of the silicone hydrogel after drying.

[0141]

[0142] Evaluation Method 6. Oxygen Permeability (Dk) Evaluation

[0143] The oxygen permeability (Dk) of the silicone hydrogels manufactured in each example was measured and evaluated using the polarographic method according to ISO 18369.

[0144]

[0145] Preparation Example 1

[0146] Preparation of silicone macromer 1

[0147] As a silicone macromer, the Hansen solubility index (HSP) is 12.0 MPa. 1 / 2 A silicone macromer 1 of the following chemical formula 2 was prepared.

[0148] [Chemical Formula 2]

[0149]

[0150] In the above chemical formula 2, a is 3, b is 3, c is 5, R1 to R4 are each a methyl group, and R5 is a butyl group.

[0151]

[0152] Preparation Example 2

[0153] Preparation of silicone macromer 2

[0154] As a silicone macromer, the Hansen solubility index (HSP) is 13.4 MPa. 1 / 2 A silicone macromer 2 of the following chemical formula 3 was prepared.

[0155] [Chemical Formula 3]

[0156]

[0157] In the above chemical formula 3, a is 3, b is 7, and R1 to R4 are each a methyl group.

[0158]

[0159] Preparation Example 3

[0160] Preparation of silicone macromer 3

[0161] As a silicone macromer, the Hansen solubility index (HSP) is 22.5 MPa. 1 / 2 A silicone macromer 3 of the following chemical formula 4 was prepared.

[0162] [Chemical Formula 4]

[0163]

[0164] In the above chemical formula 4, a is 1, b is 1, and R1 to R4 are each a methyl group.

[0165]

[0166] Preparation Example 4

[0167] Preparation of silicone macromer 4

[0168] As a silicone macromer, the Hansen solubility index (HSP) is 22.0 MPa. 1 / 2 A silicone macromer 4 of the following chemical formula 5 was prepared.

[0169] [Chemical Formula 5]

[0170]

[0171] In the above chemical formula 5, a is 1, b is 3, and R1 to R4 are each a methyl group.

[0172]

[0173] Preparation Example 5

[0174] Preparation of silicone macromer 5

[0175] As a silicone macromer, the Hansen solubility index (HSP) is 7.5 MPa. 1 / 2 A silicone macromer 5 of the following chemical formula 6 was prepared.

[0176] [Chemical Formula 6]

[0177]

[0178] In the above chemical formula 6, a is 10, b is 22, and R1 to R4 are each a methyl group.

[0179]

[0180] Preparation Example 6

[0181] Preparation of silicone macromer 6

[0182] As a silicone macromer, the Hansen solubility index (HSP) is 5.1 MPa. 1 / 2 A silicone macromer 6 of the following chemical formula 7 was prepared.

[0183] [Chemical Formula 7]

[0184]

[0185] In the above chemical formula 7, a is 12, b is 25, and R1 to R4 are each a methyl group.

[0186]

[0187] Example 1

[0188] Manufacturing of silicone gel

[0189] After mixing the ingredients shown in Table 1 below, place them in a mold and irradiate with a wavelength of 430 nm and 20 mW / cm 2 A silicone gel was manufactured by curing using a cast molding method under the conditions.

[0190] Ingredient Content (wt%) Silicone Macromer 129.7 Non-reactive Diluent IPA 5.0 Silicone Monomer DS 0.7 SIGMA 36.1 Hydrophilic Monomer HEMA 24.7 Hydrophilic Additive PVP 0.5 Crosslinker TAIC 0.7 TEGDMA 1.1 UV Protectant 2-(4-Benzoyl-3-hydroxyphenoxy)ethyl acrylate 0.9 Photoinitiator AIBN 0.6 IPA: Isopropyl Alcohol DS: Methacryloxypropyl Terminated Polydimethylsiloxane SIGMA: 2-Propenoic Acid, 2-Methyl-,2-Hydroxy-3-3-1,3,3,3-Tetramethyl-1-(trimethylsilyl)oxydisiloxanyl-propoxypropyl Ester HEMA: 2-Hydroxyethyl Methacrylate PVP: Polyvinyl Pyrrolidone TAIC: Triallyl Isocyanurate TEGDMA: Tetraethylene Glycol Dimethacrylate AIBN: 2,2'-azobisisobutyronitrile

[0191] Examples 2 to 8

[0192] Manufacturing of silicone gel

[0193] Each of the silicone gels of Examples 2 to 8 was prepared in the same manner as in Example 1, except that the components shown in Table 2 below were mixed.

[0194] Example 2345678 Ingredient content (wt%) Silicone macromer 128.126.524.923.421.820.231.3 Non-reactive diluent IPA 10.015.020.025.030.035.00.0 Silicone monomer DS 0.60.60.50.50.50.40.7 SIGMA 34.223.330.428.326.424.638.1 Hydrophilic monomer HEMA 23.422.120.819.418.116.826.0 Hydrophilic AdditivesPVP0.50.40.40.40.30.5CrosslinkerTAIC0.70.60.60.60.50.50.7TEGDMA1.01.00.90.90.80.71.2UV blocker2-(4-benzoyl-3-hydroxyphenoxy)ethyl acrylate0.90.90.90.90.90.90.9PhotoinitiatorAIBN0.60.60.60.60.60.60.60.6IPA: Isopropyl alcoholDS: Methacryloxypropyl terminated polydimethylsiloxaneSIGMA: 2-propenoic acid, 2-methyl-,2-hydroxy-3-3-1,3,3,3-tetramethyl-1-(trimethylsilyl)oxydisiloxanyl-propoxypropyl esterHEMA: 2-hydroxyethyl MethacrylatePVP: Polyvinyl pyrrolidoneTAIC: Triallyl isocyanurateTEGDMA: Tetraethylene glycol dimethacrylateAIBN: 2,2'-Azobisisobutyronitrile

[0195] Examples 9 to 15

[0196] Examples 9 to 15 are examples in which the expansion rate, moisture content, and oxygen permeability of the silicone gel in Examples 1 to 7 are evaluated, respectively, and the results are shown in Table 3 below.

[0197] E(%)W H2O (%)DK(× 10 -11 (cm 2 / s) [mLO2 / (mL·mmHg)])Example 91.4010.0070Example 100.9411.0085Example 110.9511.4091Example 120.4822.10103Example 130.0223.10110Example 140.0024.2093Example 150.0032.2090

[0198] Examples 16 and 17

[0199] Examples 16 and 17 are examples in which the swelling ratio, moisture content, and oxygen permeability of the silicone gels manufactured in Examples 7 and 8, respectively, were evaluated, and the results are shown in Table 4 below.

[0200] E(%)W H2O (%)DK(× 10 -11 (cm 2 / s) [mLO2 / (mL·mmHg)]) Example 160.0032.2090 Example 1714.016.9055

[0201] Examples 18 to 24

[0202] Examples 18 to 24 are examples in which the Hansen solubility index (HSP), dispersion power (δD), dipole attraction (δP), and hydrogen bonding power (δH) of each silicone-containing composition used in the production of silicone gels in Examples 1 to 7, respectively, were evaluated, and the results are shown in Table 5 below.

[0203] HSP (MPa) of silicone-containing composition 1 / 2 )δD(MPa 1 / 2 )δP(MPa 1 / 2 )δH(MPa 1 / 2 )Embodiment 1816.3913.904.987.11Embodiment 1916.6714.005.077.48Embodiment 2016.9514.105.157.86Embodiment 2117.2314.205.248.24Embodiment 2217.5314.305.328.62Embodiment 2317.8214.405.419.00Embodiment 2418.1214.505.499.38

[0204] Examples 25 to 28

[0205] Manufacturing of silicone gel

[0206] Except that the following non-reactive diluent was additionally added to the composition of the silicone gel of Example 8 and mixed with the components shown in Table 6 below, silicone gels of Examples 25 to 28 were prepared in the same manner as in Example 1. In addition, the results of evaluating the expansion ratio and moisture content of the silicone gels prepared in Examples 25 to 28 were compared with the results of evaluating the expansion ratio and moisture content of the silicone gel prepared in Example 8, and the results are shown in Table 6 below.

[0207] Example 8 Example 25 Example 26 Example 27 Example 28 Component content (wt%) Silicone macromer 131.321.821.821.821.8 Non-reactive diluent IPA (molar volume: 60.1 cm 3 / mol)-30.0--BE(molar volume: 118.2cm 3 / mol)--30.0-octanol (molar volume: 130.2 cm 3 / mol)---30.0Water(Molar volume: 18.01cm 3 / mol)----30.0Silicone monomerDS0.70.50.50.50.5SIGMA38.126.426.426.426.4Hydrophilic monomerHEMA26.018.118.118.118.1Hydrophilic additivePVP0.50.40.40.40.4CrosslinkerTAIC0.70.50.50.50.5TEGDMA1.20.80.80.80.8UV blocker2-(4-benzoyl-3-hydroxyphenoxy)ethyl acrylate0.90.90.90.90.9PhotoinitiatorAIBN0.60.60.60.60.6Physical propertiesE (%)14.010.001.021.0316.01W H20(%)6.9024.2022.0025.5024.00IPA: Isopropyl alcoholBE: ButoxyethanolDS: Methacryloxypropyl terminated polydimethylsiloxaneSIGMA: 2-Propenoic acid, 2-methyl-,2-hydroxy-3-3-1,3,3,3-tetramethyl-1-(trimethylsilyl)oxydisiloxanyl-propoxypropyl esterHEMA: 2-hydroxyethyl methacrylatePVP: Polyvinyl pyrrolidoneTAIC: Triallyl isocyanurateTEGDMA: Tetraethylene glycol dimethacrylateAIBN: 2,2'-Azobisisobutyronitrile

[0208] Examples 29 to 32

[0209] Examples 29 to 32 are examples in which the Hansen solubility index (HSP), dispersion power (δD), dipole attraction (δP), hydrogen bonding force (δH), polymer-solvent interaction coefficient (χ), and Gibbs free energy change (△G) of each silicone-containing composition used in the production of silicone gels in Examples 25 to 28, respectively, were evaluated, and the results are shown in Table 7 below.

[0210] HSP (MPa) of silicone-containing composition 1 / 2 )δD(MPa 1 / 2 )δP(MPa 1 / 2 )δH(MPa 1 / 2 )χ△G Example 2917.8214.405.419.000.42-6.57×10 23 Example 3017.6814.525.268.610.72-2.40×10 23 Example 3117.2214.464.788.040.91-1.76×10 23 Example 3225.5714.029.0619.370.99-7.02×10 24

[0211] Example 33

[0212] Manufacturing of silicone gel

[0213] A silicone gel of Example 33 was prepared in the same manner as Example 1, except that the components shown in Table 8 below were mixed.

[0214] Ingredient Content (wt%) Silicone Macromer 244.1 Non-reactive Diluent IPA 10.0 Hydrophilic Monomer HEMA 44.1 Hydrophilic Additive NVP 0.9 Photoinitiator AIBN 0.9 IPA: Isopropyl Alcohol HEMA: 2-Hydroxyethyl Methacrylate NVP: N-Vinyl Pyrrolidone AIBN: 2,2'-Azobisisobutyronitrile

[0215] Examples 34 to 37

[0216] Manufacturing of silicone gel

[0217] Silicone gels of Examples 34 to 37 were prepared in the same manner as in Example 1, except that the components shown in Table 9 below were mixed.

[0218] Example 34 Example 35 Example 36 Example 37 Ingredient content (wt%) Silicone macromer 239.2 34.3 29.4 49.0 Non-reactive diluent IPA 20.0 30.0 40.0 0.0 Hydrophilic monomer HEMA 39.2 34.3 29.4 49.0 Hydrophilic additive NVP 0.8 0.7 0.6 1.0 Photoinitiator AIBN 0.8 0.7 0.6 1.0 IPA: Isopropyl alcohol HEMA: 2-hydroxyethyl methacrylate NVP: N-vinyl pyrrolidone AIBN: 2,2'-azobisisobutyronitrile

[0219] Examples 38 to 41

[0220] Examples 38 to 41 are examples in which the expansion rate, moisture content, and oxygen permeability of the silicone gels manufactured in Examples 33 to 36, respectively, were evaluated, and the results are shown in Table 10 below.

[0221] E(%)W H2O (%)DK(× 10 -11 (cm 2 / s) [mLO2 / (mL·mmHg)])Example 384.9815.21110Example 395.0118.20130Example 404.9920.43142Example 410.0021.02145

[0222] Examples 42 and 43

[0223] Examples 42 and 43 are examples in which the swelling ratio, moisture content, and oxygen permeability of the silicone gels manufactured in Examples 35 and 37, respectively, were evaluated, and the results are shown in Table 11 below.

[0224] E(%)W H2O (%)DK(× 10 -11 (cm 2 / s) [mLO2 / (mL·mmHg)])Example 424.9920.43142Example 430.001.0250

[0225] Examples 44 to 47

[0226] Examples 44 to 47 are examples in which the Hansen solubility index (HSP), dispersion power (δD), dipole attraction (δP), and hydrogen bonding power (δH) of each silicone-containing composition used in the production of silicone gels in Examples 33 to 36, respectively, were evaluated, and the results are shown in Table 12 below.

[0227] HSP (MPa) of silicone-containing composition 1 / 2 )D(MPa 1 / 2 )P(MPa 1 / 2 )H(MPa 1 / 2 ) Example 4418.0313.596.1410.13 Example 4518.4913.846.1910.59 Example 4618.9614.086.2411.06 Example 4719.4314.336.2911.52

[0228] Examples 48 to 50

[0229] Manufacturing of silicone gel

[0230] Except that the following non-reactive diluent was additionally added to the composition of the silicone gel of Example 37 and mixed with the components shown in Table 13 below, silicone gels of Examples 48 to 50 were prepared in the same manner as in Example 1. In addition, the results of evaluating the expansion ratio and moisture content of the silicone gels prepared in Examples 48 to 50 were compared with the results of evaluating the expansion ratio and moisture content of the silicone gel prepared in Example 37, and the results are shown in Table 13 below.

[0231] Example 37 Example 48 Example 49 Example 50 Ingredient content (wt%) Silicone macromer 249.0 34.3 34.3 34.3 Non-reactive diluent IPA (molar volume: 60.1 cm 3 / mol)-30.0--BE(molar volume: 118.2cm 3 / mol)--30.0-octanol (molar volume: 130.2 cm 3 / mol)---30.0Hydrophilic monomerHEMA49.034.334.334.3Hydrophilic additiveNVP1.00.70.70.7PhotoinitiatorAIBN1.00.70.70.7PropertyE (%)0.004.990.010.01W H20 (%)1.0220.4316.7115.07IPA: Isopropyl alcoholBE: ButoxyethanolHEMA: 2-Hydroxyethyl methacrylateNVP: N-Vinyl pyrrolidoneAIBN: 2,2'-Azobisisobutyronitrile

[0232] Examples 51 to 53

[0233] Examples 51 to 53 are examples in which the Hansen solubility index (HSP), dispersion power (δD), dipole attraction (δP), hydrogen bonding force (δH), polymer-solvent interaction coefficient (χ), and Gibbs free energy change (△G) of each silicone-containing composition used in the production of silicone gels in Examples 48 to 50, respectively, were evaluated, and the results are shown in Table 14 below.

[0234] HSP (MPa) of composition containing recon 1 / 2 )D(MPa 1 / 2 )P(MPa 1 / 2 )H(MPa 1 / 2 )χ△G Example 5118.9614.086.2411.060.37-4.97×10 23 Example 5218.7714.206.0910.670.64-2.09×10 23 Example 5318.1414.145.6110.100.82-1.60×10 23

[0235] Example 54

[0236] Manufacturing of silicone gel

[0237] A silicone gel of Example 54 was prepared in the same manner as in Example 1, except that a non-reactive diluent was additionally added to the composition of the silicone gel of Example 37 and mixed with the components shown in Table 15 below. In addition, the results of evaluating the expansion rate and moisture content of the silicone gel prepared in Example 54 were compared with the results of evaluating the expansion rate and moisture content of the silicone gel prepared in Example 37, and the results are shown in Table 15 below.

[0238] Example 37 Example 54 Ingredient content (wt%) Silicone macromer 249.02 1.8 Non-reactive diluent BE 0.05 5.0 Hydrophilic monomer HEMA 49.02 1.8 Hydrophilic additive NVP 1.0 0.7 Photoinitiator AIBN 1.0 0.7 Physical property E (%) 0.00 13.04 W H20 (%)1.0219.00BE: ButoxyethanolHEMA: 2-Hydroxyethyl methacrylateNVP: N-Vinyl pyrrolidoneAIBN: 2,2'-Azobisisobutyronitrile

[0239] Example 55

[0240] Example 55 is an example in which the Hansen solubility index (HSP), dispersion power (δD), dipole attraction (δP), hydrogen bonding force (δH), polymer-solvent interaction coefficient (χ), and Gibbs free energy change (△G) of the silicone-containing composition used in the manufacture of the silicone gel in Example 54 were evaluated, and the results are shown in Table 16 below.

[0241] HSP (MPa) of silicone-containing composition 1 / 2 )δD(MPa 1 / 2 )δP(MPa 1 / 2 )δH(MPa 1 / 2 )χ△G Example 5520.8416.307.5010.600.90-3.0×10 22

[0242] Examples 56 and 57

[0243] Manufacturing of silicone gel

[0244] Silicone gels of Examples 56 and 57 were prepared in the same manner as in Example 1, except that a non-reactive diluent was additionally added to the composition of the silicone gel of Example 8 and mixed with the components shown in Table 17 below. In addition, the results of evaluating the expansion rate and moisture content of the silicone gels prepared in Examples 56 and 57, respectively, were compared with the results of evaluating the expansion rate and moisture content of the silicone gel prepared in Example 8, and the results are shown in Table 17 below.

[0245] Example 8 Example 56 Example 57 Ingredient content (wt%) Silicone macromer 131.3 15.2 16.2 Non-reactive diluent IPA 0.0 5 5.0 5 3.0 Silicone monomer DS 0.7 0.4 0.4 SIGMA 38.1 14.6 15.6 Hydrophilic monomer HEMA 26.0 11.8 11.8 Hydrophilic additive PVP 0.5 0.3 0.3 Crosslinker TAIC 0.7 0.5 0.5 TEGDMA 1.2 0.7 0.7 UV blocker 2-(4-benzoyl-3-hydroxyphenoxy) ethyl acrylate 0.9 0.9 0.9 Photoinitiator AIBN 0.6 0.6 0.6 Physical property E (%) 14.0 120.03 18.05 W H20 (%)6.9015.0430.08IPA: Isopropyl alcoholDS: Methacryloxypropyl terminated polydimethylsiloxaneSIGMA: 2-Propenoic acid, 2-methyl-,2-hydroxy-3-3-1,3,3,3-tetramethyl-1-(trimethylsilyl)oxydisiloxanyl-propoxypropyl esterHEMA: 2-hydroxyethyl methacrylatePVP: Polyvinyl pyrrolidoneTAIC: Triallyl isocyanurateTEGDMA: Tetraethylene glycol dimethacrylateAIBN: 2,2'-Azobisisobutyronitrile

[0246] Examples 58 and 59

[0247] Examples 58 and 59 are examples in which the Hansen solubility index (HSP), dispersion power (δD), dipole attraction (δP), hydrogen bonding force (δH), polymer-solvent interaction coefficient (χ), and Gibbs free energy change (△G) of each silicone-containing composition used in the production of silicone gels in Examples 56 and 57, respectively, were evaluated, and the results are shown in Table 18 below.

[0248] HSP (MPa) of silicone-containing composition 1 / 2 )δD(MPa 1 / 2 )δP(MPa 1 / 2 )δH(MPa 1 / 2 )χ△G Example 5818.9216.205.248.240.20-8.1×10 23 Example 5922.6018.308.1010.500.90-10×10 23

[0249] Examples 60 to 63

[0250] Manufacturing of silicone gel

[0251] Each of the silicone gels of Examples 60 to 63 was prepared in the same manner as Example 33, except that the components shown in Table 19 below were mixed.

[0252] Example 60 Example 61 Example 62 Example 63 Ingredient content (wt%) Silicone macromer 334.34 34.35 34.36 34.3 Non-reactive diluent IPA 30.0 30.0 30.0 30.0 Hydrophilic monomer HEMA 34.3 34.3 334.3 334.3 Hydrophilic additive NVP 0.7 0.7 0.7 0.7 Photoinitiator AIBN 0.7 0.7 0.7 0.7 IPA: Isopropyl alcohol HEMA: 2-hydroxyethyl methacrylate NVP: N-vinyl pyrrolidone AIBN: 2,2'-azobisisobutyronitrile

[0253] Examples 64 to 67

[0254] Examples 64 to 67 are examples in which the Hansen solubility index (HSP), dispersion power (δD), dipole attraction (δP), hydrogen bonding force (δH), polymer-solvent interaction coefficient (χ), and Gibbs free energy change (△G) of each silicone-containing composition used in the production of silicone gels in Examples 60 to 63, respectively, were evaluated, and the results are shown in Table 20 below.

[0255] HSP (MPa) of silicone-containing composition 1 / 2 )δD(MPa 1 / 2 )δP(MPa 1 / 2 )δH(MPa 1 / 2 )Х△G Example 6422.3916.857.5112.690.00-2.20×10 23 Example 6523.8118.048.1012.270.00-1.74×10 23 Example 6611.898.943.916.810.59-3.57×10 23 Example 677.543.275.978.240.62-4.00×10 23

[0256] Examples 68 to 71

[0257] Examples 68 to 71 are examples in which the expansion rate, moisture content, and oxygen permeability of the silicone gels manufactured in Examples 60 to 63 are evaluated, respectively, and the results are shown in Table 21 below.

[0258] E(%)W H20 (%)Dk(× 10 -11 (cm 2 / s) [mLO2 / (mL·mmHg)])Example 680.001.0230Example 690.000.0123Example 7012.0616.0471Example 7115.0120.0375

Claims

1. Containing a silicone macromer and a non-reactive diluent, wherein the Hansen solubility index (HSP) of the silicone macromer is 10.0 MPa. 1 / 2 Up to 20.0 MPa 1 / 2 A silicone hydrogel obtained by polymerizing a silicone-containing composition and undergoing a hydration reaction; and A contact lens comprising a hardware device.

2. Containing a silicone macromer and a non-reactive diluent, wherein the Hansen solubility index (HSP) of the silicone macromer is 10.0 MPa. 1 / 2 Up to 20.0 MPa 1 / 2 A silicone hydrogel obtained by polymerizing a silicone-containing composition and undergoing a hydration reaction; and Contact lenses containing ocular medications.

3. In paragraph 1 or 2, The above silicone-containing composition has a dispersion power (δD) of 13.3 MPa. 1 / 2 Up to 15.0 MPa 1 / 2 and the dipole force (δP) is 4.5 MPa. 1 / 2 Up to 6.6 MPa 1 / 2 , and the hydrogen bonding strength (δH) is 6.8 MPa. 1 / 2 Up to 12.0 MPa 1 / 2 In contact lenses.

4. In paragraph 1 or 2, The above silicone-containing composition is a contact lens having a polymer-solvent interaction coefficient (χ) of 0.30 to 0.

99.

5. In paragraph 1 or 2, The above silicone-containing composition has a Gibbs free energy change (△G) of -9 × 10 23 -3.5 × 10 22 In contact lenses.

6. In paragraph 1 or 2, The above silicone macromer is a contact lens represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, n is 5 to 20, R1 is a (meth)acryloyl group, R2 is an alkylene group having 1 to 40 carbon atoms, and the methylene group included in the alkylene group may be substituted with -O-, -N(R9)- or a carbonyl group, and R9 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R3 to R6 are each independently hydrogen, a hydroxyl group, an amino group, a carboxyl group, a halogen atom or an alkyl group having 1 to 3 carbon atoms, and the alkyl group may be substituted with a hydroxyl group, an isocyanate group, a halogen atom, a carboxyl group or an alkoxy group having 1 to 8 carbon atoms. R7 is a single bond or an alkylene group having 1 to 30 carbon atoms, and the methylene group included in the alkylene group is -O-, -N(R 10 )- or may be substituted with a carbonyl group, R 10 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R8 is hydrogen, a hydroxyl group, an isocyanate group, an amino group, a carboxyl group, a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or a (meth)acryloyl group.

7. In paragraph 1 or 2, A contact lens, wherein the non-reactive diluent is at least one selected from the group consisting of organic acid solvents, alcohol solvents, hydrocarbon solvents, and ketone solvents.

8. In paragraph 1 or 2, A contact lens wherein the non-reactive diluent is an aliphatic alcohol having 1 to 13 carbon atoms.

9. In paragraph 1 or 2, The above non-reactive diluent has a molar volume of 20 cm 3 / mol to 800 cm 3 / mol contact lenses.

10. In paragraph 1 or 2, A contact lens comprising the non-reactive diluent in an amount of greater than 0 wt% and less than 50 wt%.

11. In paragraph 1 or 2, A contact lens, wherein the silicone-containing composition further comprises at least one selected from the group consisting of a silicone monomer, a hydrophilic monomer, a hydrophilic additive, an amphiphilic polymer, a crosslinking agent, an ultraviolet ray blocking agent, and an initiator.

12. In paragraph 1, A lens body comprising the above silicone hydrogel and formed to be wearable on the cornea; A protective layer comprising the above silicone hydrogel and laminated on the lens body; and A contact lens comprising a hardware device inserted between the lens body and the protective layer.

13. In paragraph 1 or 2, The above silicone hydrogel is a contact lens having an expansion ratio (E) of 9% or less of the following general formula 1: [General Formula 1] In the above general formula 1, a is the area of ​​the silicone gel before the hydration reaction, and b is the area of ​​the silicone hydrogel after the hydration reaction.

14. In paragraph 1 or 2, The above silicone hydrogel is a contact lens having a moisture content of 10% or more.

15. In paragraph 1 or 2, The above silicone hydrogel has an oxygen permeability of 60 × 10 -11 (cm 2 / s)[mLO2 / (mL·mmHg)] to 160 × 10 -11 (cm 2 Contact lenses with a volume of / s)[mLO2 / (mL·mmHg)].

16. A silicone macromer and a non-reactive diluent, wherein the Hansen solubility index (HSP) of the silicone macromer is 10.0 MPa. 1 / 2 Up to 20.0 MPa 1 / 2 A step of inserting a hardware device into a silicone-containing composition; A step of polymerizing a silicone-containing composition into which the hardware device is inserted to produce a silicone gel into which the hardware device is inserted; and A method for manufacturing a contact lens, comprising a step of manufacturing a silicone hydrogel in which the hardware device is inserted by subjecting the polymerized silicone gel to a hydration reaction.

17. A silicone macromer comprising a silicone macromer and a non-reactive diluent, wherein the Hansen solubility index (HSP) of the silicone macromer is 10.0 MPa. 1 / 2 Up to 20.0 MPa 1 / 2 A step of mixing an ocular drug into a silicone-containing composition; A step of polymerizing a silicone-containing composition mixed with the ocular drug to produce a silicone gel containing the ocular drug; and A method for manufacturing a contact lens, comprising a step of manufacturing a silicone hydrogel loaded with an ocular drug by subjecting the polymerized silicone gel to a hydration reaction.

18. In paragraph 16 or 17, A method for manufacturing a contact lens in which, during the above hydration reaction, the non-reactive diluent contained in the silicone gel is replaced with water through a hydration reaction.

19. A silicone macromer comprising a silicone macromer and a non-reactive diluent, wherein the silicone macromer has a Hansen solubility index (HSP) of 10.0 MPa. 1 / 2 Up to 20.0 MPa 1 / 2 a step of polymerizing a silicone-containing composition; and A method for manufacturing a contact lens, comprising a step of manufacturing a silicone hydrogel loaded with an ocular drug by subjecting the polymerized silicone gel to a hydration reaction with an ocular drug solution.

20. In paragraph 19, A method for manufacturing a contact lens, wherein, during the above hydration reaction, some or all of the non-reactive diluent contained in the silicone gel is replaced with the ocular drug through a hydration reaction.

Images