Contact lens and method of manufacturing the same

Abstract

The present invention has a technical problem to provide a contact lens having hydrophilicity, lubricity and anti-lipid adhesion, and a manufacturing method of the contact lens. As a solution, the present invention has found that a contact lens obtained by surface treatment of a contact lens substrate having an epoxy group-containing organosilicon macromonomer in its composition with a hydrophilic polymer by using the hydrophilic polymer in combination with the contact lens substrate containing a specific composition can solve the above technical problem.

Description

Technical Field

[0001] This invention relates to a contact lens and a method for manufacturing the same, the contact lens comprising a hydrophilic polymer and a contact lens substrate being an epoxy group-containing silicone macromer. More specifically, this invention relates to a contact lens and a method for manufacturing the same, the contact lens being formed by surface treatment of a contact lens substrate having an epoxy group-containing silicone macromer in its composition using a hydrophilic polymer.

[0002] This application claims priority to Japanese Application No. 2021-104496, which is cited in this application by reference. Background Technology

[0003] Compared to existing hydrogel lenses, silicone hydrogel contact lenses exhibit significantly higher oxygen permeability due to the incorporation of silicone. Consequently, their market share in the contact lens market has been steadily increasing in recent years, and their future popularity is anticipated to grow even further. However, because silicone hydrogel contact lenses are inherently hydrophobic, they tend to repel tears and are prone to attracting lipid deposits. Therefore, silicone hydrogel contact lenses typically require surface modification to improve their hydrophilicity, lubricity, and lipid adhesion.

[0004] Various methods have been employed for surface modification. For example, one method includes plasma treatment as a manufacturing process for commercially available silicone hydrogel contact lenses. The advantages of plasma treatment are high hydrophilicity and durability. However, on the other hand, there is a possibility of reduced lubricity.

[0005] One approach that doesn't require high equipment investment is to add a wetting agent to the lens compound. The advantage of this approach is that since the wetting agent is added before contact lens molding, post-molding surface treatment is unnecessary. However, on the other hand, because it is used simultaneously with the silicone component in the lens compound, there is a possibility of impairing transparency.

[0006] As another approach, one could cite the method of applying a wetting agent to the surface of contact lenses. It is known that when a large amount of hydrophilic polymers are used as wetting agents, especially when using 2-methacryloyloxyethyl phosphorylcholine {2-(methacryloyloxy)ethyl-2'-(trimethylamino)ethyl phosphate, hereinafter sometimes abbreviated as MPC} which has an amphoteric structure, high hydrophilicity and lubricity can be obtained.

[0007] In Patent Document 1, the synthesis of copolymers of MPC was studied. However, the application of the illustrated copolymers to the coating of silicone hydrogel contact lenses was not investigated.

[0008] Patent document 2 investigated a coating for silicone hydrogel contact lenses formed from copolymers of MPC. However, since the coating was not covalently bonded to the contact lens, durability issues arose, indicating room for improvement in the coating method.

[0009] Patent documents 3 and 4 investigated the covalent bonding of hydrophilic polymers to the surface of silicone hydrogel contact lenses. However, there is still room for improvement in the surface's hydrophilicity, lubricity, and resistance to lipid adhesion.

[0010] In addition, there have been reports in recent years on lid-wiper epitheliopathy (LWE), which suggests that increased friction between the palpebral conjunctiva (palpebral limb) and the surface of the eye caused by blinking leads to the shedding and modification of the epithelium on the surface of the palpebral conjunctiva (Non-Patent Literature 1, Non-Patent Literature 2).

[0011] As an eye condition, limbal erosion (LWE) caused by friction between the palpebral conjunctiva and the surface of the eye has attracted attention. Therefore, contact lenses with highly hydrophilic and lubricating surfaces are needed.

[0012] Existing technical documents

[0013] Patent documents

[0014] Patent Document 1: U.S. Patent No. 6,090,901

[0015] Patent Document 2: International Publication No. 2013 / 074535

[0016] Patent Document 3: U.S. Patent No. 6,087,415

[0017] Patent Document 4: International Publication No. 2001 / 074932

[0018] Non-patent literature

[0019] Non-patent literature 1: DRKorb et al., 2002, CLAO J, 28, 211-216.

[0020] Non-patent literature 2: DRKorb et al., 2005, Eye & Contact Lens, 31, 2-8. Summary of the Invention

[0021] The technical problem to be solved by the present invention

[0022] The technical problem of the present invention is to provide a contact lens with hydrophilicity, lubricity and anti-lipid adhesion properties, and a method for manufacturing the contact lens.

[0023] Technical means to solve technical problems

[0024] In order to solve the above-mentioned technical problems, the inventors of this application conducted a careful study and found that the above-mentioned technical problems can be solved by combining a hydrophilic polymer containing a specific composition with a contact lens substrate containing a specific composition and then using the hydrophilic polymer to perform surface treatment on the contact lens substrate having an epoxy-containing organosilicon macromonomer in its composition, thereby completing the contact lens of the present invention.

[0025] That is, the contact lenses disclosed herein are as follows.

[0026] 1. A contact lens comprising a hydrophilic polymer and a contact lens substrate, characterized in that,

[0027] The hydrophilic polymer is a polymer containing a structural monomer based on at least one of 2-aminoethyl methacrylate or methacrylic acid.

[0028] The contact lens substrate is a substrate having an epoxy-containing organosilicon macromonomer as shown in formula (1) in its composition.

[0029] The hydrophilic polymer is bonded to the contact lens substrate via at least one covalent bond selected from the group consisting of formulas (A-1) to (B-2) below.

[0030] [Chemical Formula 1]

[0031]

[0032] In equation (1), a is an integer from 10 to 500, and b is an integer from 1 to 100; R 1 and R 2 Each can be used independently to represent a hydrogen atom or a methyl group; R 3 and R 4 Each is independently an alkylene divalent group having 2 to 6 carbon atoms or a -R group. 5 -OR 6 - a divalent group, wherein R 5 and R 6 Each is an alkylene divalent group with 2 to 6 carbon atoms, independent of the others; X 0 As shown in equation (2) or equation (3) below,

[0033] [Chemical Formula 2]

[0034]

[0035] In equation (2), R 7 It is an alkylene divalent group with 2 to 8 carbon atoms or -R 9 -OR 10 - a divalent group, wherein R 9 and R 10 Each is an alkylene divalent group with 1 to 6 carbon atoms, independent of the others; R 8 Indicates a hydrogen atom or a methyl group.

[0036] [Chemical Formula 3]

[0037]

[0038] In equation (3), R 11 It is an alkylene divalent group with 2 to 8 carbon atoms or -R 12 -OR 13 - a divalent group, wherein R 12 and R 13 Each of them is an alkylene divalent group with 1 to 6 carbon atoms.

[0039] [Chemical Formula 4]

[0040]

[0041] 2. A method for manufacturing a contact lens, characterized in that,

[0042] The manufacturing method includes a step of contacting a hydrophilic polymer with a contact lens substrate.

[0043] The hydrophilic polymer is a polymer containing a structural monomer based on at least one of 2-aminoethyl methacrylate or methacrylic acid.

[0044] The contact lens substrate is a substrate having an epoxy-containing organosilicon macromonomer as shown in formula (1) in its composition.

[0045] In this process, at least one covalent bond is formed from the group consisting of the following formulas (A-1) to (B-2).

[0046] [Chemical Formula 5]

[0047]

[0048] In equation (1), a is an integer from 10 to 500, and b is an integer from 1 to 100; R 1 and R 2 Each can be used independently to represent a hydrogen atom or a methyl group; R 3 and R 4 Each is independently an alkylene divalent group having 2 to 6 carbon atoms or a -R group.5 -OR 6 - a divalent group, wherein R 5 and R 6 Each is an alkylene divalent group with 2 to 6 carbon atoms, independent of the others; X 0 As shown in equation (2) or equation (3) below,

[0049] [Chemical Formula 6]

[0050]

[0051] In equation (2), R 7 It is an alkylene divalent group with 2 to 8 carbon atoms or -R 9 -OR 10 - a divalent group, wherein R 9 and R 10 Each is an alkylene divalent group with 1 to 6 carbon atoms, independent of the others; R 8 Indicates a hydrogen atom or a methyl group.

[0052] [Chemical Formula 7]

[0053]

[0054] In equation (3), R 11 It is an alkylene divalent group with 2 to 8 carbon atoms or -R 12 -OR 13 - a divalent group, wherein R 12 and R 13 Each of them is an alkylene divalent group with 1 to 6 carbon atoms.

[0055] [Chemical Formula 8]

[0056]

[0057] 3. The contact lens according to item 1 above, wherein the hydrophilic polymer is a copolymer further comprising a structural monomer based on the monomer shown in formula (4) below.

[0058] [Chemical Formula 9]

[0059]

[0060] In equation (4), R 14 It represents a hydrogen atom or a methyl group.

[0061] 4. The method for manufacturing contact lenses according to item 2 above, wherein the hydrophilic polymer is a copolymer further comprising a structural monomer based on the monomer shown in formula (4) below.

[0062] [Chemical Formula 10]

[0063]

[0064] In equation (4), R 14 It represents a hydrogen atom or a methyl group.

[0065] 5. A method of use, characterized in that it is a method for manufacturing contact lenses using a polymer containing a structural monomer based on at least one of 2-aminoethyl methacrylate or methacrylic acid and an epoxy-containing organosilicon macromonomer as shown in formula (1) below.

[0066] [Chemical Formula 11]

[0067]

[0068] In equation (1), a is an integer from 10 to 500, and b is an integer from 1 to 100; R 1 and R 2 Each can be used independently to represent a hydrogen atom or a methyl group; R 3 and R 4 Each is independently an alkylene divalent group having 2 to 6 carbon atoms or a -R group. 5 -OR 6 - a divalent group, wherein R 5 and R 6 Each is an alkylene divalent group with 2 to 6 carbon atoms, independent of the others; X 0 As shown in equation (2) or equation (3) below,

[0069] [Chemical Formula 12]

[0070]

[0071] In equation (2), R 7 It is an alkylene divalent group with 2 to 8 carbon atoms or -R 9 -OR 10 - a divalent group, wherein R 9 and R 10 Each is an alkylene divalent group with 1 to 6 carbon atoms, independent of the others; R 8 Indicates a hydrogen atom or a methyl group.

[0072] [Chemical Formula 13]

[0073]

[0074] In equation (3), R 11 It is an alkylene divalent group with 2 to 8 carbon atoms or -R 12 -OR 13 - a divalent group, wherein R 12 and R13 Each of them is an alkylene divalent group with 1 to 6 carbon atoms.

[0075] The contact lens comprises the hydrophilic polymer and a contact lens substrate having an epoxy-containing organosilicon macromonomer as shown in formula (1) in its composition.

[0076] The hydrophilic polymer is bonded to the contact lens substrate via at least one covalent bond selected from the group consisting of formulas (A-1) to (B-2) below.

[0077] [Chemical Formula 14]

[0078]

[0079] 6. The contact lens according to item 1 or 3 above, wherein the hydrophilic polymer is a polymer containing a structural monomer based on 2-aminoethyl methacrylate, and in formula (1) of the epoxy-containing organosilicon macromonomer, a is an integer from 30 to 280, b is an integer from 1 to 70, and R 1 For -CH3, R 2 For -CH3, R 3 For -CH2CH2CH2-, R 4 For -CH2CH2CH2-, X 0 For equation (2){R 7 For -CH2CH2CH2-O-CH2-, R 8 For -H}.

[0080] 7. The contact lens according to item 1 or 3 above, wherein the hydrophilic polymer is a polymer containing a structural monomer based on methacrylic acid, and in the epoxy-containing organosilicon macromonomer shown in formula (1), a is an integer from 30 to 280, b is an integer from 1 to 70, and R 1 For -CH3, R 2 For -CH3, R 3 For -CH2CH2CH2-, R 4 For -CH2CH2CH2-, X 0 For equation (2){R 7 -CH2CH2CH2-O-CH2-, R 8 For -H}.

[0081] 8. A contact lens substrate comprising, in its composition, an epoxy-containing organosilicon macromonomer as shown in formula (1),

[0082] [Chemical Formula 15]

[0083]

[0084] In equation (1), a is an integer from 10 to 500, and b is an integer from 1 to 100; R 1 and R 2 Each can be used independently to represent a hydrogen atom or a methyl group; R 3 and R 4 Each is independently an alkylene divalent group having 2 to 6 carbon atoms or a -R group. 5 -OR 6 - a divalent group, wherein R 5 and R 6 Each is an alkylene divalent group with 2 to 6 carbon atoms, independent of the others; X 0 As shown in equation (2) or equation (3) below,

[0085] [Chemical Formula 16]

[0086]

[0087] In equation (2), R 7 It is an alkylene divalent group with 2 to 8 carbon atoms or -R 9 -OR 10 - a divalent group, wherein R 9 and R 10 Each is an alkylene divalent group with 1 to 6 carbon atoms, independent of the others; R 8 Indicates a hydrogen atom or a methyl group.

[0088] [Chemical Formula 17]

[0089]

[0090] In equation (3), R 11 It is an alkylene divalent group with 2 to 8 carbon atoms or -R 12 -OR 13 - a divalent group, wherein R 12 and R 13 Each of them is an alkylene divalent group with 1 to 6 carbon atoms, which are independent of each other.

[0091] Invention Effects

[0092] The contact lenses of the present invention are hydrophilic, lubricating, and anti-lipid adhesion. Detailed Implementation

[0093] The contact lens of the present invention comprises a hydrophilic polymer and a contact lens substrate, wherein the hydrophilic polymer is a polymer containing a structural monomer based on at least one of 2-aminoethyl methacrylate or methacrylic acid, and the contact lens substrate comprises an epoxy-containing organosilicon macromonomer. The contact lens is characterized in that the hydrophilic polymer and the contact lens substrate are bonded by covalent bonds.

[0094] In the method for manufacturing contact lenses of the present invention, a hydrophilic polymer is fixed to a contact lens substrate by covalent bonds. More specifically, a covalent bond is formed between a structural monomer contained in the hydrophilic polymer based on at least one of 2-aminoethyl methacrylate or methacrylic acid, and the epoxy group of an epoxy-containing organosilicon macromonomer contained in the contact lens substrate. In this case, the hydrophilic polymer is fixed onto the organosilicon macromonomer. Through this fixation, in the organosilicon contact lens, the hydrophilic polymer is fixed to the organosilicon portion where lipids easily adhere, thus achieving excellent lipid adhesion inhibition.

[0095] Furthermore, in the contact lens and its manufacturing method of the present invention, it is not necessary to form covalent bonds between the hydrophilic polymer and the contact lens substrate at all possible reactive sites. That is, for the contact lens and its manufacturing method of the present invention, a portion of unreacted 2-aminoethyl methacrylate or methacrylic acid, a portion of unreacted epoxy-containing organosilicon macromonomers, and a portion of the epoxy groups in the epoxy-containing organosilicon macromonomers may remain in an unreacted state.

[0096] <About hydrophilic polymers>

[0097] The hydrophilic polymer disclosed herein is a polymer containing a structural monomer based on at least one of 2-aminoethyl methacrylate or methacrylic acid.

[0098] Structural monomers refer to the units of compounds contained in polymers based on or derived from individual monomers.

[0099] That is, the hydrophilic polymer can be a polymer containing either an aminoethyl methacrylate-based structural monomer or a methacrylic acid-based structural monomer, or a copolymer containing both an aminoethyl methacrylate-based structural monomer and a methacrylic acid-based structural monomer. The structural monomer (hereinafter, sometimes abbreviated as "reactive monomer") based on at least one of aminoethyl methacrylate or methacrylic acid forms a covalent bond with the contact lens substrate.

[0100] In addition, in this specification, "2-aminoethyl methacrylate" also includes its hydrochloric acid adduct structure. That is, 2-aminoethyl methacrylate contains 2-aminoethyl methacrylate hydrochloride.

[0101] Furthermore, in this specification, "methacrylic acid" also includes its metal salt structure. That is, methacrylic acid contains a metal salt of methacrylate. For example, methacrylic acid may also contain sodium methacrylate or potassium methacrylate.

[0102] The hydrophilic polymer of the present invention may further contain structural units based on a monomer (hereinafter sometimes abbreviated as "PC monomer") shown in formula (4). The PC monomer in the hydrophilic polymer is introduced to improve the hydrophilicity, lubricity and anti-lipid adhesion of the contact lens surface.

[0103] [Chemical Formula 18]

[0104]

[0105] In equation (4), R 14 It represents a hydrogen atom or a methyl group.

[0106] From the perspective of availability, R in formula (4) is preferred as the PC monomer in the hydrophilic polymer. 14 MPC represents methyl groups.

[0107] Without compromising the effectiveness of the contact lenses of the present invention, the hydrophilic polymer of the present invention may contain monomers other than the reactive monomer and the PC monomer.

[0108] Other monomers include, for example, polymerizable monomers selected from linear or branched alkyl esters of (meth)acrylate, cyclic alkyl esters of (meth)acrylate, (meth)acrylates containing aromatic groups, styrene monomers, vinyl ether monomers, vinyl ester monomers, (meth)acrylates containing hydrophilic hydroxyl groups, and monomers containing nitrogen-containing groups.

[0109] Additionally, in this specification, "(meth)acrylate" means "alkyl acrylate or alkyl methacrylate", and other similar terms are the same.

[0110] Examples of linear or branched alkyl esters of (meth)acrylate include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, lauryl (meth)acrylate, and stearate (meth)acrylate.

[0111] Examples of cycloalkyl esters of (meth)acrylate include cyclohexyl (meth)acrylate.

[0112] Examples of (meth)acrylates containing aromatic groups include benzyl (meth)acrylate and phenoxyethyl (meth)acrylate.

[0113] Examples of styrene monomers include styrene, methylstyrene, and chlorostyrene.

[0114] Examples of vinyl ether monomers include methyl vinyl ether and butyl vinyl ether.

[0115] Examples of vinyl ester monomers include vinyl acetate and vinyl propionate.

[0116] Examples of (meth)acrylates containing hydrophilic hydroxyl groups include polyethylene glycol (meth)acrylate, polypropylene glycol (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, and 4-hydroxybutyl (meth)acrylate.

[0117] Monomers containing nitrogen-containing groups include, for example, N-vinylpyrrolidone, N-vinylacetamide, and N-vinyl-N-methylacetamide.

[0118] When the hydrophilic polymer is a copolymer composed solely of the reactive monomer and the PC monomer, if the molar ratio of the reactive monomer in the hydrophilic polymer is set as n... A Set the molar ratio of PC monomers to n. B Then the molar ratio n of each structural monomer A :n B The ratio is 5-80:20-95. Or, in the case of n... A When n is set to 100, B The range is 25 to 1900.

[0119] When the molar ratio n of the reactive monomers A Below this range, there is a possibility that sufficient bonds may not be formed with the contact lens substrate. When the molar ratio n of the PC monomer... B Below the stated range, there is a possibility that the contact lenses may not be adequately endowed with hydrophilicity, lubricity, and anti-lipid adhesion.

[0120] When the hydrophilic polymer is a copolymer composed of the reactive monomer, the PC monomer, and other monomers, if the molar ratio of the reactive monomers in the hydrophilic polymer is set as m... A Set the molar ratio of PC monomers to m. B Set the molar ratio of other monomers as m C Then the preferred molar ratio m of each structural monomer is... A :m B :m C The ratio is 4-80:19-95:1-50. Or, in the case of m... A When set to 100, m B The value ranges from 23.75 to 2375 m. C It ranges from 1.25 to 1250.

[0121] When the molar ratio of the reactive monomers is m A Below this range, there is a possibility that sufficient bonds may not be formed with the contact lens substrate. When the molar ratio of the PC monomers m BBelow the stated range, there is a possibility that the contact lenses may not be adequately endowed with hydrophilicity, lubricity, and anti-lipid adhesion.

[0122] The hydrophilic polymer has a weight-average molecular weight of 10,000 to 5,000,000, preferably 12,000 to 4,000,000, more preferably 14,000 to 3,000,000, and even more preferably 16,000 to 2,000,000.

[0123] If the weight-average molecular weight is less than 10,000, there is a possibility that it will be difficult to separate from impurities during manufacturing. When the weight-average molecular weight is greater than 5,000,000, there is a possibility that the viscosity will increase and filtration will become difficult.

[0124] The weight-average molecular weight of hydrophilic polymers refers to the value obtained by gel permeation chromatography (GPC).

[0125] Hydrophilic polymers can be obtained by free radical polymerization of a reactive monomer composition of a hydrophilic polymer. The preparation of hydrophilic polymers can be carried out, for example, by free radical polymerization of a reactive monomer composition of a hydrophilic polymer in the presence of a free radical polymerization initiator, under an atmosphere of inert gas replacement such as nitrogen, carbon dioxide, argon, or helium. Regarding the polymerization method, known methods such as bulk polymerization, suspension polymerization, emulsion polymerization, and solution polymerization can be used. From the perspective of purification, solution polymerization is preferred. The purification of hydrophilic polymers can be carried out using known purification methods such as reprecipitation, dialysis, and ultrafiltration.

[0126] Examples of free radical polymerization initiators include azo radical polymerization initiators, organic peroxides, and persulfates.

[0127] Examples of azo radical polymerization initiators include 2,2'-azobis(2-methylpropanediamine) dihydrochloride, 2,2-azobis(2-diaminopropyl) dihydrochloride, 2,2-azobis(2-(5-methyl-2-imidazolin-2-yl)propane) dihydrochloride, 4,4-azobis(4-cyanopentanoic acid), 2,2-azobisisobutylamide dihydrate, 2,2-azobis(2,4-dimethylpentanonitrile), and 2,2-azobisisobutyronitrile (AIBN).

[0128] Examples of organic peroxides include tert-butyl peroxyneodecanate (PERBUTYL (registered trademark) ND), benzoyl peroxide, diisopropyl peroxydicarbonate, tert-butyl peroxy-2-ethylhexanoate, tert-butyl peroxyneodecanate, tert-butyl peroxydiisobutyrate, lauroyl peroxide, and succinic acid peroxide (=succinic acid peroxide).

[0129] Examples of persulfates include ammonium persulfate, potassium persulfate, and sodium persulfate.

[0130] These free radical polymerization initiators can be used alone, or in combination of two or more. The amount of polymerization initiator used is typically 0.001 to 10 parts by weight, preferably 0.01 to 5.0 parts by weight, relative to 100 parts by weight of the monomer composition of the hydrophilic polymer.

[0131] The preparation of the hydrophilic polymer of the present invention can be carried out in the presence of a solvent. The solvent can be any solvent that dissolves the reactive monomer composition of the hydrophilic polymer; examples include water, alcohols, ketones, esters, linear or cyclic ethers, and nitrogen-containing solvents.

[0132] Examples of alcohol solvents include methanol, ethanol, n-propanol, and isopropanol.

[0133] Examples of ketone solvents include acetone, methyl ethyl ketone, and diethyl ketone.

[0134] Examples of ester solvents include ethyl acetate.

[0135] Examples of linear or cyclic ether solvents include ethyl cellosolve and tetrahydrofuran.

[0136] Examples of nitrogen-containing solvents include acetonitrile, nitromethane, and N-methylpyrrolidone.

[0137] <About epoxy-containing organosilicon macromonomers>

[0138] In the contact lens and the method for manufacturing the contact lens of the present invention, the contact lens comprises the hydrophilic polymer described above and the contact lens substrate.

[0139] The epoxy-containing organosilicon macromonomer contained in the composition (structure) of the contact lens substrate of the present invention is as shown in the following formula (1).

[0140] [Chemical Formula 19]

[0141]

[0142] In equation (1), a is an integer from 10 to 500, and b is an integer from 1 to 100. 1 and R 2 Each can be used to represent a hydrogen atom or a methyl group independently. R 3 and R 4 Each is independently an alkylene divalent group having 2 to 6 carbon atoms or a -R group. 5 -OR 6 - a divalent group, wherein R 5and R 6 Each of them is an alkylene divalent group with 2 to 6 carbon atoms. X 0 As shown in equation (2) or equation (3) below.

[0143] [Chemical Formula 20]

[0144]

[0145] In equation (2), R 7 It is an alkylene divalent group with 2 to 8 carbon atoms or -R 9 -OR 10 - a divalent group, wherein R 9 and R 10 Each is an independent alkylene divalent group having 1 to 6 carbon atoms. 8 It represents a hydrogen atom or a methyl group.

[0146] [Chemical Formula 21]

[0147]

[0148] In equation (3), R 11 It is an alkylene divalent group with 2 to 8 carbon atoms or -R 12 -OR 13 - a divalent group, wherein R 12 and R 13 Each of them is an alkylene divalent group with 1 to 6 carbon atoms, which are independent of each other.

[0149] If a and b are within the above range, there is no particular limitation. a is 10 to 500, preferably 10 to 300, more preferably 10 to 200, even more preferably 15 to 100, particularly preferably 20 to 70, and most preferably 20 to 50.

[0150] b is 1 to 100, preferably 1 to 70, more preferably 2 to 30, even more preferably 2 to 15, and particularly preferably 3 to 10.

[0151] When 'a' is below the above range, there is a possibility that the contact lens may become hard and brittle. When 'a' is above the above range, from a compatibility perspective, there is a possibility that the synthesis of the contact lens substrate may become difficult.

[0152] When b is below the above range, there is a possibility that the hydrophilic polymer is not sufficiently fixed to the contact lens substrate; when b is above the above range, there is a possibility that the mechanical properties suitable for contact lenses may be impaired.

[0153] Furthermore, it is possible to combine and modify the various ranges (preferred ranges, more preferred ranges, etc.) of a and b. For example, a can be selected as a more preferred range while b is selected as a particularly preferred range.

[0154] Additionally, in this specification, the term "alkylene group having 2 to 6 carbon atoms" refers to a divalent group obtained by removing two hydrogen atoms from an alkyl group having 2 to 6 carbon atoms. Other similar terms are treated the same. Alkylene groups (or free radicals) form two bonds with other groups in organic compounds.

[0155] The epoxy-containing organosilicon macromonomer shown in formula (1) is synthesized through the following two processes.

[0156] In the first step, the precursor of the epoxy-containing organosilicon macromonomer shown in formula (5) is synthesized by any method known to those skilled in the art (see: Japanese Patent No. 5490547, Japanese Patent Publication No. 62-29776). For example, the precursor of the epoxy-containing organosilicon macromonomer of formula (5) is synthesized by polymerization of a mixture of octamethylcyclotetrasiloxane (D4) and 1,3,5,7-tetramethylcyclotetrasiloxane (D'4) in the presence of 1,3-bis[3-(meth)acryloyloxypropyl]tetramethyldisiloxane as a terminal block, for example by a reaction catalyzed by an acid catalyst such as trifluoromethanesulfonic acid. By controlling the molar ratio of the terminal block, D4, and D'4, a and b in formula (5) can be obtained with the desired values.

[0157] [Chemical Formula 22]

[0158]

[0159] In equation (5), a is an integer from 10 to 500, and b is an integer from 1 to 100. 1 and R 2 Each can be used to represent a hydrogen atom or a methyl group independently. R 3 and R 4 Each is independently an alkylene divalent group having 2 to 6 carbon atoms or a -R group. 5 -OR 6 - a divalent group, wherein R 5 and R 6 Each of them is an alkylene divalent group with 2 to 6 carbon atoms, which are independent of each other.

[0160] In the second step, in a platinum-catalyzed hydrosilylation reaction known to those skilled in the art, the precursor of the epoxy-containing organosilicon macromonomer shown in formula (5) is reacted with an enemonomer having an epoxy group to synthesize the epoxy-containing organosilicon macromonomer shown in formula (1), which contains an organic substituent having an epoxy group.

[0161] An epoxy group is an olefin monomer that has both vinyl and epoxy groups in one molecule. Examples of such compounds include 2-methyl-2-vinyl ethylene oxide, 3,4-epoxy-1-butene, 1,2-epoxy-5-hexene, allyl glycidyl ether, 1,2-epoxy-9-decene, and 1,2-epoxy-4-vinylcyclohexane (equivalent to formula (3)), which are commercially available.

[0162] <Contact Lens Substrate>

[0163] The contact lens substrate of the present invention is a substrate containing the epoxy-containing organosilicon macromonomer in its composition, and a covalent bond is formed between it and the hydrophilic polymer.

[0164] Relative to the monomer composition of 100 parts by weight of the contact lens substrate, the composition of the epoxy-containing organosilicon macromonomer in the contact lens substrate of the present invention is typically 1 to 50 parts by weight, preferably 5 to 45 parts by weight, and more preferably 10 to 40 parts by weight.

[0165] In addition to the epoxy-containing organosilicon macromonomers, the contact lens substrate of the present invention contains (I) organosilicon-containing vinyl monomers, (II) organosilicon-free hydrophobic vinyl monomers, (III) non-organosilicon vinyl crosslinking agents, (IV) hydrophilic vinyl monomers, (V) UV-absorbing vinyl monomers, and any combination of these monomers.

[0166] Relative to 100 parts by weight of the monomer composition of the contact lens substrate of the present invention, the composition of (I) of the contact lens substrate of the present invention containing organosilicon vinyl monomers is generally 7 to 55 parts by weight, preferably 10 to 50 parts by weight, and more preferably 13 to 35 parts by weight.

[0167] Relative to 100 parts by weight of the monomer composition of the contact lens substrate of the present invention, the composition of the (II) silicone-free hydrophobic vinyl monomer of the contact lens substrate of the present invention is generally 1 to 50 parts by weight, preferably 2 to 30 parts by weight, and more preferably 5 to 25 parts by weight.

[0168] Relative to 100 parts by weight of the monomer composition of the contact lens substrate of the present invention, the composition of the (III) non-organosilicon vinyl crosslinking agent of the contact lens substrate of the present invention is generally 0.01 to 10 parts by weight, preferably 0.1 to 10 parts by weight, and more preferably 0.2 to 5 parts by weight.

[0169] Relative to 100 parts by weight of the monomer composition of the contact lens substrate of the present invention, the composition of the (IV) hydrophilic vinyl monomer of the contact lens substrate of the present invention is generally 5 to 80 parts by weight, preferably 10 to 75 parts by weight, and more preferably 15 to 70 parts by weight.

[0170] Relative to 100 parts by weight of the monomer composition of the contact lens substrate of the present invention, the composition of the (V)UV-absorbing vinyl monomer of the contact lens substrate of the present invention is generally 0.01 to 20 parts by weight, preferably 0.1 to 10 parts by weight, and more preferably 0.5 to 5 parts by weight.

[0171] As the organosilicon-containing vinyl monomer described in (I), any suitable organosilicon-containing vinyl monomer can be used. Preferred organosilicon-containing vinyl monomers contain tris(trialkylsiloxy)silyl or bis(trialkylsiloxy)alkylsilyl. Examples of such preferred organosilicon-containing vinyl monomers are not limited, but include 3-acrylamidopropyl-bis(trimethylsiloxy)methylsilane, 3-N-methacrylamidopropyl-bis(trimethylsiloxy)methylsilane, N-[tris(trimethylsiloxy)silylpropyl]-(methyl)acrylamide, N-[tris(dimethylpropylsiloxy)silylpropyl]-(methyl)acrylamide, N-[tris(dimethylphenylsiloxy)silylpropyl](methyl)acrylamide, N-[tris(dimethylethylsiloxy)silylpropyl](methyl)acrylamide, etc. [2-hydroxy-3-(3-(bis(trimethylsiloxy)methylsilyl)propoxy)propyl]-2-methylacrylamide; N-(2-hydroxy-3-(3-(bis(trimethylsiloxy)methylsilyl)propoxy)propyl)acrylamide; N,N-bis[2-hydroxy-3-(3-(bis(trimethylsiloxy)methylsilyl)propoxy)propyl]-2-methylacrylamide; N,N-bis[2-hydroxy-3-(3-(bis(trimethylsiloxy)methylsilyl)propoxy)propyl]-2-methylacrylamide; [2-hydroxy-3-(3-(tris(trimethylsiloxy)silyl)propoxy)propyl]acrylamide; N-(2-hydroxy-3-(3-(tris(trimethylsiloxy)silyl)propoxy)propyl)-2-methylacrylamide; N-(2-hydroxy-3-(3-(tris(trimethylsiloxy)silyl)propoxy)propyl)acrylamide; N,N-bis[2-hydroxy-3-(3-(tris(trimethylsiloxy)silyl)propoxy)propyl]-2-methylacrylamide; N,N-bis[2-hydroxy-3-(3-(tris(trimethylsiloxy)silyl)propoxy)propyl]-2-methylacrylamide; [Silyloxy)silyl)propoxy)propyl]acrylamide; N-[2-hydroxy-3-(3-(tert-butyldimethylsilyl)propoxy)propyl]-2-methylacrylamide; N-[2-hydroxy-3-(3-(tert-butyldimethylsilyl)propoxy)propyl]acrylamide; N,N-bis[2-hydroxy-3-(3-(tert-butyldimethylsilyl)propoxy)propyl]-2-methylacrylamide; N,N-bis[2-hydroxy-3-(3-(tert-butyldimethylsilyl)propoxy)propyl]acrylamide;3-Methacryloxypropylpentamethyldisiloxane, tris(trimethylsiloxy)methacrylate (TRIS), (3-methacryloxy-2-hydroxypropoxy)propylbis(trimethylsiloxy)methylsilane (SIGMA), (3-methacryloxy-2-hydroxypropoxy)propyltris(trimethylsiloxy)silane, 3-(trimethylsilyl)propylvinyl carbonate, 3-(ethyleneoxycarbonylthio)propyltris(trimethyl-siloxy)silane, 3-[ Tris(trimethylsiloxy)silyl]propyl vinyl carbamate, 3-[tri(trimethylsiloxy)silyl]propyl allyl carbamate, 3-[tri(trimethylsiloxy)silyl]propyl vinyl carbonate, tert-butyldimethyl-siloxyethyl vinyl carbonate, trimethylsilyl ethyl vinyl carbonate, trimethylsilyl methyl vinyl carbonate, 4-(2-hydroxyethyl)-1-[3-tris(trimethylsiloxy)silylpropyl]-2-methylene succinate, etc.

[0172] Other preferred types of organosilicon-containing vinyl monomers are vinyl monomers containing polydimethylsiloxanes. Examples of such polydimethylsiloxane-containing vinyl monomers are mono-(meth)acryloyl-terminated polydimethylsiloxanes of various molecular weights (e.g., mono-3-methacryloyloxypropyl-terminated, mono-butyl-terminated, or mono-(3-methacryloyloxy-2-hydroxypropoxy)propyl-terminated, mono-butyl-terminated polydimethylsiloxanes of various molecular weights), mono-(meth)acrylamide-terminated polydimethylsiloxanes of various molecular weights, or combinations of these monomers.

[0173] The organosilicon-containing vinyl monomer (I) is preferably 3-(meth)acryloyloxy-2-hydroxypropoxy)propylbis(trimethylsiloxy)methylsilane, 3-(meth)acryloyloxyethoxypropoxypropylbis(trimethylsiloxy)methylsilane, 3-(meth)acrylamidopropyl-bis(trimethylsiloxy)methylsilane, 3-N-methyl(meth)acrylamidopropylbis(trimethylsiloxy)methylsilane, 4-(2-hydroxyethyl)-1-[3-tris(trimethylsiloxy)silylpropyl]-2-methylene succinate, mono-(meth)acryloyl-terminated polydimethylsiloxanes of various molecular weights, mono-(meth)acrylamide-terminated polydimethylsiloxanes of various molecular weights, or combinations of these monomers.

[0174] The (II) silicone-free hydrophobic vinyl monomer can be any suitable hydrophobic vinyl monomer. Examples of preferred hydrophobic vinyl monomers include methyl acrylate, ethyl acrylate, propyl acrylate, isopropyl acrylate, cyclohexyl acrylate, 2-ethylhexyl acrylate, methyl methacrylate, ethyl methacrylate, propyl methacrylate, vinyl acetate, vinyl propionate, vinyl butyrate, vinyl valerate, styrene, chloroprene, vinyl chloride, vinylidene chloride, acrylonitrile, 1-butene, butadiene, methacrylonitrile, vinyltoluene, vinyl ethyl ether, perfluorohexylethyl-thio-carbonyl-aminoethyl-methacrylate, isobornyl methacrylate, trifluoroethyl methacrylate, hexafluoroisopropyl methacrylate, and hexafluorobutyl methacrylate.

[0175] The (III) non-organosilicone vinyl crosslinking agent can be any suitable non-organosilicone vinyl crosslinking agent. Examples of preferred non-organosilicone crosslinking agents are not limited, but include tetraethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, ethylene glycol di(meth)acrylate, tetraethylene glycol divinyl ether, triethylene glycol divinyl ether, diethylene glycol divinyl ether, ethylene glycol divinyl ether, trimethylolpropane trimethacrylate, pentaerythritol tetramethacrylate, bisphenol A dimethacrylate, vinyl methacrylate, ethylenediamine di-(meth)acrylamide, glycerol dimethacrylate, triallyl isocyanurate, triallyl cyanurate, allyl (meth)acrylate, N-allyl-(meth)acrylamide, 1,3-bis(methacrylamidopropyl)-1,1,3,3-tetra(trimethylsilyl)acrylate. The product of diamines (preferably selected from the group consisting of N,N'-bis(hydroxyethyl)ethylenediamine, N,N'-dimethylethylenediamine, ethylenediamine, N,N'-dimethyl-1,3-propanediamine, N,N'-diethyl-1,3-propanediamine, 1,3-propanediamine, 1,4-butanediamine, 1,5-pentanediamine, hexamethylenediamine, isophoronediamine, and combinations thereof) and epoxy-containing vinyl monomers (preferably selected from the group consisting of glycidyl methacrylate, vinyl glycidyl ether, allyl glycidyl ether, and combinations thereof), and combinations thereof. More preferably, the crosslinking agent is selected from the group consisting of tetra(ethylene glycol) di(meth)acrylate, tri(ethylene glycol) di(meth)acrylate, ethylene glycol di(meth)acrylate, di(ethylene glycol) di(meth)acrylate, glycerol dimethacrylate, allyl (meth)acrylate, N,N'-methylenebis(meth)acrylamide, N,N'-ethylenebis(meth)acrylamide, N,N'-dihydroxyethylenebis(meth)acrylamide, triallyl isocyanurate, tetraethylene glycol divinyl ether, triethylene glycol divinyl ether, diethylene glycol divinyl ether, ethylene glycol divinyl ether, and combinations thereof.

[0176] The (IV) hydrophilic vinyl monomer can be any suitable hydrophilic vinyl monomer. Examples of preferred hydrophilic vinyl monomers are not limited, but include N-vinylpyrrolidone, N,N-dimethyl (meth)acrylamide, (meth)acrylamide, hydroxyethyl (meth)acrylamide, hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, hydroxybutyl (meth)acrylate, glycerol methacrylate, polyethylene glycol (meth)acrylate, polyethylene glycol C1-C4 alkyl ether (meth)acrylates having a number average molecular weight of up to 1500, N- Vinylformamide, N-vinylacetamide, N-vinylisopropylamide, N-vinyl-N-methylacetamide, N-methyl-3-methylene-2-pyrrolidone, 1-ethyl-3-methylene-2-pyrrolidone, 1-methyl-5-methylene-2-pyrrolidone, 1-ethyl-5-methylene-2-pyrrolidone, 5-methyl-3-methylene-2-pyrrolidone, 5-ethyl-3-methylene-2-pyrrolidone, (meth)acrylic acid, ethyl acrylate, MPC, and combinations thereof. The hydrophilic vinyl monomer is preferably hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, hydroxybutyl (meth)acrylate, N-vinylpyrrolidone, N-vinyl-N-methylacetamide, N-vinylformamide, N-vinylacetamide, N-vinylisopropylamide, or combinations thereof. The hydrophilic vinyl monomer is more preferably hydroxyethyl (meth)acrylate, N-vinylpyrrolidone, N-vinyl-N-methylacetamide, or a combination of these monomers.

[0177] The (V) UV-absorbing vinyl monomer can be any suitable UV-absorbing vinyl monomer. Examples of preferred UV-absorbing vinyl monomers are not limited, but include 2-(2-hydroxy-5-vinylphenyl)-2H-benzotriazole, 2-(2-hydroxy-5-acrylyloxyphenyl)-2H-benzotriazole, 2-(2-hydroxy-3-methylacrylamide methyl-5-tert-octylphenyl)benzotriazole, 2-(2'-hydroxy-5'-methylacrylamide phenyl)-5-chlorobenzotriazole, and 2-(2'-hydroxy-5'-methylacrylamide phenyl)-5-methoxyphenyl 2-(2'-hydroxy-5'-methacryloyloxypropyl-3'-tert-butyl-phenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy-5'-methacryloyloxypropylphenyl)benzotriazole, 2-hydroxy-5-methoxy-3-(5-(trifluoromethyl)-2H-benzo[d][1,2,3]triazol-2-yl)benzyl methacrylate, 2-hydroxy-5-methoxy-3-(5-methoxy-2H-benzo[d][1,2,3]triazol-2-yl)benzyl methacrylate, 3-( 5-Fluoro-2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methoxybenzyl methacrylate, 3-(2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methoxybenzyl methacrylate, 3-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-2-hydroxy-5-methoxybenzyl methacrylate, 2-hydroxy-5-methoxy-3-(5-methyl-2H-benzo[d][1,2,3]triazol-2-yl)benzyl 2-hydroxy-5-methyl-3-(5-(trifluoromethyl)-2H-benzo[d][1,2,3]triazol-2-yl)benzyl methacrylate, 4-allyl-2-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-6-methoxyphenol, 2-{2'-hydroxy-3'-tert-5'[3”-(4”-vinylbenzyloxy)propoxy]phenyl}-5-methoxy-2H-benzotriazole, 2-(5-chloro-2H-benzotriazol-2-yl)-6-(1,1-Dimethylethyl)-4-vinylphenol, 2-(2'-hydroxy-5'-methacryloyloxyethylphenyl)benzotriazole (2-methyl-2-[3-(2H-benzotriazole-2-yl)-4-hydroxyphenyl]ethyl ester, Norbloc), 2-{2'-hydroxy-3'-tert-butyl-5'-[3'-methacryloyloxypropoxy]phenyl}-5-methoxy-2H-benzotriazole, 2-[2'-hydroxy-3'-tert-butyl-5'-(3'-acryloyloxypropoxy)phenyl]-5-trifluoromethyl-2H-benzotriazole 2-(2'-hydroxy-5-methylacrylamidephenyl)-5-methoxybenzotriazole, 2-(3-allyl-2-hydroxy-5-methylphenyl)-2H-benzotriazole, 2-(2-hydroxy-3-methylallyl-5-methylphenyl)-2H-benzotriazole, 2-3'-tert-butyl-2'-hydroxy-5'-(3”-dimethylvinylsilylpropoxy)-2'-hydroxy-phenyl)-5-methoxybenzotriazole, 2-(2'-hydroxy-5'-methacryloylpropyl-3'-tert-butyl-phenyl)-5-methoxy-2H-benzotriazole.

[0178] The contact lens substrate of the present invention is synthesized by copolymerizing an epoxy-containing organosilicon macromonomer with a polymerizable composition, said polymerizable composition comprising (I) an organosilicon-containing vinyl monomer, (II) an organosilicon-free hydrophobic vinyl monomer, (III) an organosilicon-free vinyl crosslinking agent, (IV) a hydrophilic vinyl monomer, (V) a UV-absorbing vinyl monomer, and any combination thereof. In the copolymerization reaction, any solvent, any thermal initiator, or photoinitiator as a free radical initiator of the copolymerization reaction can be used.

[0179] Furthermore, the synthesis method is not particularly limited, and various methods known to those skilled in the art can be used. For example, the composition can be mixed, uniformly dissolved, dispensed into a contact lens mold, and polymerized by irradiation with visible or UV light for a specified time, thereby obtaining a contact lens substrate.

[0180] Examples of suitable solvents are not limited, but may include tetrahydrofuran, tripropylene glycol methyl ether, dipropylene glycol methyl ether, ethylene glycol n-butyl ether, acetone, methyl ethyl ketone, diethylene glycol n-butyl ether, diethylene glycol methyl ether, ethylene glycol phenyl ether, propylene glycol methyl ether, propylene glycol methyl ether acetate, dipropylene glycol methyl ether acetate, propylene glycol n-propyl ether, dipropylene glycol n-propyl ether, tripropylene glycol n-butyl ether, propylene glycol n-butyl ether, dipropylene glycol n-butyl ether, tripropylene glycol n-butyl ether, propylene glycol phenyl ether, dipropylene glycol dimethyl ether, polyethylene glycol, polypropylene glycol, ethyl acetate, butyl acetate, amyl acetate, methyl lactate, ethyl lactate, isopropyl lactate. Dichloromethane, 2-butanol, 1-propanol, 2-propanol, menthol, 1-hexanol, cyclohexanol, cyclopentanol and its derivatives - norborneol, 2-pentanol, 3-pentanol, 2-hexanol, 3-hexanol, 3-methyl-2-butanol, 2-heptanol, 2-octanol, 2-nonanol, 2-decanol, 3-octanol, norborneol, tert-butanol, tert-pentanol, 2-methyl-2-pentanol, 2,3-dimethyl-2-butanol, 3-methyl-3-pentanol, 1-methylcyclohexanol, 2-methyl-2-hexanol, 3,7-dimethyl-3-octanol, 1-chloro-2-methyl-2-propanol, 2-methyl-2-heptanol, 2-methyl 2-Octanol, 2-Methyl-2-nonanol, 2-Methyl-2-decanol, 3-Methyl-3-hexanol, 3-Methyl-3-heptanol, 4-Methyl-4-heptanol, 3-Methyl-3-octanol, 4-Methyl-4-octanol, 3-Methyl-3-nonanol, 4-Methyl-4-nonanol, 3-Methyl-3-octanol, 3-Ethyl-3-hexanol, 3-Methyl-3-heptanol, 4-Ethyl-4-heptanol, 4-propyl-4-heptanol, 4-isopropyl-4-heptanol, 2,4-dimethyl-2-pentanol, 1-methylcyclopentanol, 1-ethylcyclopentanol, 1-ethylcyclopentanol, 3-hydroxy-3-methyl The following are included: 1-butene, 4-hydroxy-4-methyl-1-cyclopentanol, 2-phenyl-2-propanol, 2-methoxy-2-methyl-2-propanol, 2,3,4-trimethyl-3-pentanol, 3,7-dimethyl-3-octanol, 2-phenyl-2-butanol, 2-methyl-1-phenyl-2-propanol, 3-ethyl-3-pentanol, 1-ethoxy-2-propanol, 1-methyl-2-propanol, tert-amyl alcohol, isopropanol, 1-methyl-2-pyrrolidone, N,N-dimethylpropionamide, dimethylformamide, dimethylacetamide, dimethylpropionamide, N-methylpyrrolidone, and mixtures of these solvents.

[0181] Suitable thermal polymerization initiators are well known to those skilled in the art, and include, for example, peroxides, hydrogen peroxide, azobis(alkyl or cycloalkyl nitrile), persulfates, percarbonates, or mixtures of these thermal polymerization initiators. Examples include benzoyl peroxide, tert-butyl peroxide, di-tert-butyl peroxyphthalate, tert-butyl hydrogen peroxide, azobis(isobutyronitrile) (AIBN), 1,1-azobisisobutyramidine, 1,1'-azobis(cyclohexane-1-carboxynitrile), and 2,2'-azobis(2,4-dimethylpentanonitrile). Polymerization is preferably carried out in the above-mentioned solvent at a temperature of 25–140°C, preferably in the above-mentioned solvent at a temperature of 40–120°C. The reaction time can vary within a wide range, for example, preferably 1–24 hours or preferably 2–12 hours. It is preferable to degas the components and solvent used in the polymerization reaction beforehand, or to purge them with nitrogen or argon.

[0182] Suitable photoinitiators include benzoin methyl ether, diethoxyacetophenone, benzoylphosphine oxide, 1-hydroxycyclohexylphenyl ketone, and Darocur and Irgacure types, preferably Darocur 1173, Darocur 2959, Irgacure 819, and germane-type Norish I photoinitiators. Examples of benzoylphosphine oxide initiators include 2,4,6-trimethylbenzoyldiphenylphosphine oxide; bis-(2,6-dichlorobenzoyl)-4-N-propylphenylphosphine oxide; and bis-(2,6-dichlorobenzoyl)-4-N-butylphenylphosphine oxide. Reactive photoinitiators capable of incorporating macromonomers or used as specific monomers are also suitable.

[0183] Polymerization reactions can be carried out in the atmosphere, but to increase the polymerization rate, they can also be carried out in an inert gas atmosphere such as nitrogen or argon. When polymerizing in an inert gas atmosphere, it is preferable to set the pressure in the polymerization system to 1 kgf / cm². 2 the following.

[0184] After polymerization, the contact lens substrate is peeled from the mold using known methods, allowing it to be removed in a dry state. Alternatively, the contact lens substrate and mold can be immersed together in a solvent (e.g., water, methanol, ethanol, 1-propanol, 2-propanol, and mixtures thereof) to swell and peel off. Furthermore, repeated immersion in these solvents can be performed for cleaning to remove residues, byproducts, etc., thus producing the contact lens substrate.

[0185] Examples of solvents used for cleaning include water, methanol, ethanol, 1-propanol, 2-propanol, and mixtures thereof. For example, the polymer can be immersed in these solvents at a temperature of 10°C to 40°C for 10 minutes to 10 hours. After cleaning, it is then immersed in water for displacement.

[0186] <Covalent bonds between hydrophilic polymers and contact lens substrates>

[0187] The hydrophilic polymer of the present invention has at least one covalent bond selected from the group consisting of the following formulas (A-1), (A-2), (B-1), and (B-2) between it and the contact lens substrate of the present invention. This covalent bond is formed through the reaction of a reactive monomer in the hydrophilic polymer with an epoxy-containing organosilicon macromonomer in the contact lens substrate.

[0188] The following formulas (A-1) and (A-2) are formed by the reaction of 2-aminoethyl methacrylate in a hydrophilic polymer with an epoxy-containing organosilicon macromonomer in a contact lens substrate.

[0189] Formulas (B-1) and (B-2) below are formed by the reaction of methacrylic acid in a hydrophilic polymer with epoxy-containing organosilicon macromonomers in a contact lens substrate.

[0190] [Chemical Formula 23]

[0191]

[0192] Covalent bonds between hydrophilic polymers and contact lens substrates can be obtained by treating the hydrophilic polymers and contact lens substrates at high temperatures of 60–200°C for 10 minutes to 10 hours. In this case, covalent bond formation can occur under high pressure conditions, for example, by performing a pressure heat treatment at 121°C for 20 minutes.

[0193] To catalyze the reaction, methyldiethanolamine, triethylamine, sodium hydroxide, potassium hydroxide, etc., can be added.

[0194] A hydrophilic polymer solution is prepared by dissolving a hydrophilic polymer in water or physiological saline at a concentration of about 0.01 to about 10 parts by weight, preferably 0.1 to 5.0 parts by weight. Typically, the amount of the hydrophilic polymer solution used for each contact lens substrate is 0.1 g to 100 g, preferably 0.5 g to 50 g, and more preferably 0.5 g to 10 g.

[0195] After the reaction, the surface of the resulting contact lenses is rinsed with water or saline solution to remove byproducts.

[0196] (Example of the structure of the contact lens of the present invention)

[0197] The following examples illustrate combinations of hydrophilic polymers and epoxy-containing organosilicon macromonomers used in the manufacture of the contact lenses of the present invention, but are not limited thereto.

[0198] Hydrophilic polymer: epoxy-containing organosilicon macromonomers as shown in formula (1)

[0199] 2-Aminoethyl methacrylate: In formula (1), a is an integer from 30 to 280, b is an integer from 1 to 70, R 1 For -CH3, R 2 For -CH3, R 3 For -CH2CH2CH2-, R 4 For -CH2CH2CH2-, X 0 For equation (2){R 7 -CH2CH2CH2-O-CH2-, R 8 For -H}.

[0200] Methacrylic acid: In formula (1), a is an integer from 30 to 280, b is an integer from 1 to 70, R 1 For -CH3, R 2 For -CH3, R 3 For -CH2CH2CH2-, R 4 For -CH2CH2CH2-, X 0 For equation (2){R 7 -CH2CH2CH2-O-CH2-, R 8 For -H}.

[0201] Methacrylic acid: In formula (1), a is an integer from 30 to 280, b is an integer from 1 to 70, R 1 For -CH3, R 2 For -CH3, R 3 For -CH2CH2CH2-, R 4 For -CH2CH2CH2-, X 0 For equation (3){R 11 It is -CH2CH2-}.

[0202] 2-Aminoethyl methacrylate: In formula (1), a is an integer from 30 to 280, b is an integer from 1 to 70, R 1 For -CH3, R 2 For -CH3, R 3 For -CH2CH2CH2-, R 4 For -CH2CH2CH2-, X 0 For equation (3){R 11 It is -CH2CH2-}.

[0203] Furthermore, the hydrophilic polymers and epoxy-containing organosilicon macromonomers of the above combinations can be replaced with other combinations of hydrophilic polymers and epoxy-containing organosilicon macromonomers of formula (1) to constitute the contact lenses of this disclosure.

[0204] (Application in manufacturing contact lenses of the present invention)

[0205] In order to manufacture contact lenses, one embodiment of the present invention also includes the polymer containing at least one of the structural monomers based on 2-aminoethyl methacrylate or methacrylic acid as described above, and the method of using the epoxy-containing organosilicon macromonomer of formula (1) described above.

[0206] (The contact lens substrate of the present invention)

[0207] One embodiment of the present invention also includes a contact lens substrate containing an epoxy-containing organosilicon macromonomer of formula (1) described above.

[0208] Example

[0209] The contact lenses and contact lens substrates of the present invention will be specifically described below through examples and comparative examples, but the contact lenses and contact lens substrates of the present invention are not limited to these examples and comparative examples.

[0210] <Preparation of Hydrophilic Polymers>

[0211] ○ Preparation of hydrophilic polymers containing structural monomers based on 2-aminoethyl methacrylate as reactive monomers

[0212] [Synthesis example 1-1]

[0213] 79.27 g (0.268 mol) of MPC (manufactured by NOF CORPORATION) and 4.46 g (0.027 mol) of 2-aminoethyl methacrylate hydrochloride (manufactured by AeMA, Sigma-Aldrich) were dissolved in 330.95 g of distilled water (manufactured by Otsuka Pharmaceutical Co., Ltd.). The solution was placed in a four-necked flask and stirred at 150 rpm at 30 °C while being purged with nitrogen at 0.4 L / min for 30 minutes. The solution was then heated to 65 °C, and 0.60 g of 2,2'-azobis(2-methylpropanediamine) dihydrochloride (manufactured by Wako Pure Chemical Industries, Ltd.) was added. The 2,2'-azobis(2-methylpropanediamine) dihydrochloride adhering to the inner wall was rinsed off with 5.0 g of distilled water. The nitrogen flow rate was set to 0.2 L / min, and the solution temperature was raised to 70 °C and maintained for 120 minutes. After the polymerization reaction, the polymerization solution was added dropwise to 3 L of acetone while stirring. The precipitate was filtered and vacuum dried at room temperature for 48 hours to obtain a powder.

[0214] ○ Preparation of hydrophilic polymers containing structural monomers based on methacrylic acid (with a carboxylic acid reactive group) as reactive monomers

[0215] [Synthesis example 1-2]

[0216] 81.57 g (0.276 mol) of MPC (manufactured by NOF CORPORATION) and 2.64 g (0.031 mol) of methacrylic acid (manufactured by Kishida Chemical Co., Ltd.) were dissolved in 330.95 g of distilled water (manufactured by Otsuka Pharmaceutical Co., Ltd.). The solution was placed in a four-necked flask and stirred at 150 rpm at 30 °C while being purged with nitrogen at 0.4 L / min for 30 minutes. The solution was then heated to 65 °C, and 0.60 g of 2,2'-azobis(2-methylpropanediamine) dihydrochloride (manufactured by Wako Pure Chemical Industries, Ltd.) was added. The 2,2'-azobis(2-methylpropanediamine) dihydrochloride adhering to the inner wall was rinsed off with 5.0 g of distilled water. The nitrogen flow rate was set to 0.2 L / min, and the solution temperature was raised to 70 °C and maintained for 120 minutes. After the polymerization reaction, the polymerization solution was added dropwise to 3 liters of acetone while stirring. The precipitate was filtered and vacuum dried at room temperature for 48 hours to obtain powder.

[0217] Preparation of polymers without reactive monomers

[0218] [Synthesis Example 1-3]

[0219] 79.27 g (0.268 mol) of MPC (manufactured by NOF CORPORATION) was dissolved in 330.95 g of distilled water (manufactured by Otsuka Pharmaceutical Co., Ltd.). The solution was placed in a four-necked flask and stirred at 150 rpm at 30 °C while being purged with nitrogen at 0.4 L / min for 30 minutes. The solution was then heated to 65 °C, and 0.60 g of 2,2'-azobis(2-methylpropanediamine) dihydrochloride (manufactured by Wako Pure Chemical Industries, Ltd.) was added. The 2,2'-azobis(2-methylpropanediamine) dihydrochloride adhering to the inner wall was rinsed off with 5.0 g of distilled water. The nitrogen flow rate was set to 0.2 L / min, and the solution temperature was raised to 70 °C and maintained for 120 minutes. After the polymerization reaction, the polymerization solution was added dropwise to 3 liters of acetone while stirring. The precipitate was filtered and vacuum dried at room temperature for 48 hours to obtain powder.

[0220] Synthesis of epoxy-containing organosilicon macromonomers

[0221] The following method was used to synthesize epoxy-containing organosilicon macromonomers.

[0222] [Synthesis example 2-1]

[0223] ○ First process

[0224] In a 100 mL light-proof bottle, 8.40 g of X-22-164AS (manufactured by Shin-Etsu Chemical Co., Ltd., a dimethylmethacryloyloxypropyl polydimethylsiloxane (molecular weight ≒1,000)), 20.41 g of octamethylcyclotetrasiloxane (D4), and 0.84 g of 1,3,5,7-tetramethylcyclotetrasiloxane (D'4) were mixed, followed by the addition of 0.04 g of trifluoromethanesulfonic acid. After reacting at 25°C for 6 hours, 0.25 g of sodium bicarbonate was added to neutralize the reaction. Then, 2.97 g of sodium sulfate was added, and dehydration was carried out for 30 minutes. The sodium bicarbonate and sodium sulfate were removed by filtration, yielding 27.35 g of a clear liquid (refer to Table 1 below for precursors of epoxy-containing organosilicon macromonomers).

[0225] ○ Second process

[0226] In a 100 mL three-necked flask, 10.00 g of the above-mentioned transparent liquid (the precursor of the epoxy-containing organosilicon macromonomer described in formula (5)), 0.81 g of allyl glycidyl ether (manufactured by Tokyo Chemical Industry Co., Ltd.) (an epoxy-containing olefin monomer), and 0.01 g of butylated hydroxytoluene (manufactured by Wako Pure Chemical Industries, Ltd.) as a stabilizer were dissolved in 20.07 g of toluene (manufactured by Kishida Chemical Co., Ltd.), and 100 μL of platinum(O)-1,3-divinyltetramethyldisiloxaneacetone complex (manufactured by Sigma-Aldrich) were added. After reacting at 25 °C for 6 hours, 2.0 g of activated carbon was added, and the mixture was stirred for another 1 hour. Then, 2.0 g of sodium sulfate was added, and dehydration was carried out for 30 minutes. Then, the activated carbon and sodium sulfate were removed by filtration, and the solvent was removed under reduced pressure, thereby obtaining 9.28g of the epoxy-containing organosilicon macromonomer shown in formula (1).

[0227] The results of synthesis example 2-1 are shown in Table 1.

[0228] [Synthesis Example 2-2 to Synthesis Example 2-8]

[0229] Using the same steps as in Synthesis Example 2-1, the amounts of X-22-164AS, D4, and D'4 were changed in the first step, and allyl glycidyl ether or 1,2-epoxy-5-hexene was used instead of allyl glycidyl ether in the second step to synthesize various epoxy-containing organosilicon macromonomers as shown in Formula (1), from Synthesis Example 2-2 to Synthesis Example 2-8.

[0230] The results of Synthetic Examples 2-2 to 2-8 are shown in Table 1.

[0231] The epoxide-containing olefin monomers used in synthetic examples 2-2 to 2-8 are as follows.

[0232] Synthesis Example 2-2: Allyl glycidyl ether

[0233] Synthesis Example 2-3: Allyl glycidyl ether

[0234] Synthetic Examples 2-4: 1,2-Epoxy-5-hexene

[0235] Synthesis Examples 2-5: Allyl glycidyl ether

[0236] Synthesis Examples 2-6: Allyl glycidyl ether

[0237] Synthetic Examples 2-7: 1,2-Epoxy-5-hexene

[0238] Synthesis Examples 2-8: Allyl glycidyl ether

[0239] Synthesis of epoxy-free organosilicon macromonomers

[0240] [Synthesis example 2-9]

[0241] In a 100 mL light-proof bottle, 8.40 g of X-22-164AS (manufactured by Shin-Etsu Chemical Co., Ltd., a dimethylmethacryloyloxypropyl polydimethylsiloxane (molecular weight ≒1,000)) and 21.43 g of octamethylcyclotetrasiloxane (D4) were mixed, followed by the addition of 0.04 g of trifluoromethanesulfonic acid. After reacting at 25 °C for 6 hours, 0.25 g of sodium bicarbonate was added, and the reaction was stopped by neutralization. Then, 2.97 g of sodium sulfate was added, and dehydration was carried out for 30 minutes. The sodium bicarbonate and sodium sulfate were removed by filtration, yielding 28.39 g of the epoxy-free organosilicon macromonomer used in the comparative example.

[0242] In addition, the epoxy-free organosilicon macromonomer is equivalent to the structure of b representing 0 in formula (1).

[0243] The results of synthetic examples 2-9 are shown in Table 1.

[0244] <Synthesis of Contact Lens Substrates>

[0245] ○ Composition of contact lens substrate

[0246] 1) Epoxy-containing organosilicon macromonomers: Synthesis Examples 2-1 to 2-8

[0247] 2) Organosilicon macromonomers without epoxy groups: Synthesis Examples 2-9

[0248] ○ Composition other than epoxy-containing organosilicon macromonomers

[0249] (I) Vinyl monomers containing organosilicon: SIGMA (3-methacryloyloxy-2-hydroxypropoxy)propylbis(trimethylsiloxy)methylsilane

[0250] (III) Non-organic silicone vinyl crosslinking agent: TEGDMA (tetraethylene glycol dimethacrylate)

[0251] (IV) Hydrophilic vinyl monomers: HEMA (hydroxyethyl methacrylate), NVP (N-vinylpyrrolidone)

[0252] ○ Solvent: HeOH: 1-Hexanol

[0253] ○Polymerization initiator: I-819 (Irgacure 819)

[0254] ○ Contact lens substrate using epoxy-containing organosilicon macromonomers

[0255] [Synthesis Example 3-1]

[0256] 30.00 parts by weight of the epoxy-containing organosilicon macromonomer of Synthesis Example 2-1, 20.00 parts by weight of SIGMA, 1.00 parts by weight of TEGDMA, 10.00 parts by weight of HEMA, 39.00 parts by weight of NVP, and 30.00 parts by weight of HeOH were mixed. Then, 2.00 parts by weight of I-819 were added to prepare a composition, and the homogeneity of the composition was evaluated.

[0257] The composition was dispensed into a contact lens mold and placed inside a UV irradiation device (manufactured by CCS Inc.). The mixture was then irradiated for 30 minutes with UV light at 405 nm and 1.5 mW / cm². 2 UV light is used to obtain the polymer of the composition.

[0258] The polymer is removed from the mold and immersed in a solution of 40g of 2-propanol: ion-exchanged water = 1:1 for 2 hours, then immersed in 40g of ion-exchanged water for 1 hour, and further immersed in 40g of physiological saline for 1 hour, thereby obtaining the contact lens substrate.

[0259] The results of synthesis example 3-1 are shown in Table 2.

[0260] [Evaluation of the homogeneity of the composition]

[0261] The composition was placed in a colorless, transparent container and evaluated visually according to the following criteria.

[0262] +: Uniform and transparent

[0263] - Uneven texture, cloudy appearance, or presence of sediment, etc.

[0264] [Synthesis Example 3-2 to Synthesis Example 3-8]

[0265] Using the same steps as in Synthesis Example 3-1, the epoxy-containing organosilicon macromonomers synthesized in Synthesis Examples 2-2 to 2-8 were used to synthesize contact lens substrates, resulting in Synthesis Examples 3-2 to 3-8.

[0266] The results of synthetic examples 3-2 to 3-8 are shown in Table 2.

[0267] ○ Contact lens substrate using epoxy-free organosilicon macromonomers

[0268] [Synthesis Example 3-9]

[0269] Following the same steps as in Synthesis Example 3-1, an attempt was made to synthesize a contact lens substrate using the epoxy-free organosilicon macromonomers synthesized in Synthesis Examples 2-9. When evaluating the homogeneity of the composition, no further polymerization was performed because the result was "-".

[0270] The results of synthetic examples 3-9 are shown in Table 2.

[0271] [Synthesis Example 3-10]

[0272] Using the same steps as in Synthesis Example 3-1, the epoxy-free organosilicon macromonomer synthesized in Synthesis Examples 2-9 was used to synthesize the contact lens substrate, resulting in Synthesis Example 3-10.

[0273] The results of synthesis example 3-10 are shown in Table 2.

[0274] [Synthesis Example 3-11]

[0275] Using the same steps as in Synthesis Example 3-1, a commercially available epoxy-free organosilicon macromonomer (manufactured by Shin-Etsu Chemical Co., Ltd., product name "X22-164AS") was used to synthesize a contact lens substrate, resulting in Synthesis Example 3-11.

[0276] The synthesis results of Synthesis Example 3-11 are shown in Table 2.

[0277] <Hydrophilicity test method (Water Break-up Time (WBUT) test method)>

[0278] The hydrophilicity of the surface of the contact lens (substrate) is evaluated according to the following steps.

[0279] The contact lens (substrate) was soaked in physiological saline overnight. In a windless room, the contact lens (substrate) was removed from the saline solution and placed under illumination. The time required for the water film to rupture and the surface of the contact lens (substrate) to be exposed (WBUT) was visually recorded. Cases with a WBUT less than 5 seconds were rated "0", cases between 5 and 15 seconds were rated "1", and cases greater than 15 seconds were rated "2".

[0280] <Lubricity Test Method>

[0281] The lubricity of the surface of a contact lens (substrate) is evaluated using the following steps.

[0282] The 1-Day ACUVUE (registered trademark) (manufactured by Johnson & Johnson KK) was used as the standard for lubrication testing. Contact lenses (substrate) soaked overnight in saline solution were removed and placed on the index finger for lubrication evaluation. The lubrication evaluation was based on the 1-Day ACUVUE (registered trademark) immediately after removal from the blister pack (4 points). Increased lubrication resulted in a higher score, while decreased lubrication resulted in a lower score. Evaluation scores ranged from 1 to 10. A score of 1-3 was assigned as "0", 4-6 as "1", and 7-10 as "2".

[0283] <Anti-lipid adhesion test>

[0284] The anti-lipid adhesion properties of contact lenses (substrate) were evaluated according to the following steps.

[0285] First, the artificial lipid was prepared according to the method described below. Next, the contact lens (substrate) that had been soaked in physiological saline overnight was immersed in 4 mL of artificial lipid for 4 hours, then gently rinsed with physiological saline to remove moisture. The appearance was then visually inspected and evaluated according to the following criteria.

[0286] The observation of overall whitening of the contact lens is scored as "0", the observation of partial whitening is scored as "1", and the observation of almost no whitening is scored as "2".

[0287] Preparation of artificial lipids

[0288] 1) Mix 0.5 g of the mixed lipids with the following composition into 100 mL of the phosphate-borate buffer solution shown below.

[0289] 2) Use a homogenizer to suspend the mixture at 60°C.

[0290] 3) Adjust the pH to 7.0 using 1N hydrochloric acid.

[0291] Composition of mixed lipids

[0292]

[0293] References: Kaoru Iwai, Mari Moriyama, Masaki Imayasu, and Hideaki Tanaka: A study on lipid adhesion of contact lenses, Journal of the Japanese Society for Contact Lenses, 37, 58-61, 1995.

[0294] <Manufacturing and evaluation of contact lenses made from a hydrophilic polymer containing 2-aminoethyl methacrylate and a contact lens substrate using an epoxy-containing organosilicon macromonomer>

[0295] [Example 1-1]

[0296] The hydrophilicity, lubricity, and anti-lipid adhesion of the contact lens substrate synthesized in Synthesis Example 3-1 were evaluated. The WBUT score was "1", the lubricity score was "0", and the anti-lipid adhesion score was "1".

[0297] The hydrophilic polymer containing 2-aminoethyl methacrylate prepared in Synthesis Example 1-1 was dissolved in water to prepare a 1% hydrophilic polymer solution.

[0298] The contact lens substrate synthesized in Synthesis Example 3-1 and 5.00 g of the prepared hydrophilic polymer solution were placed in a glass vial, and 0.03 g of sodium hydroxide (NaOH) was added as a catalyst. The glass vial was sealed, and the vial was subjected to a pressure heat treatment at 121°C for 20 minutes to manufacture contact lenses.

[0299] After heat treatment, the contact lenses are removed and rinsed with 10g of saline solution. Next, the rinsed contact lenses are placed in a glass bottle, 10g of saline solution is added, and the bottle is sealed tightly. The bottle is then heat-treated at 121°C for 20 minutes to obtain contact lenses in which the hydrophilic polymer is coated onto the contact lens substrate via covalent bonds of formula (A-1) or (A-2).

[0300] The hydrophilicity, lubricity, and anti-lipid adhesion of the obtained contact lenses were evaluated. The WBUT score was "2", the lubricity score was "1", and the anti-lipid adhesion score was "2".

[0301] The evaluation of the contact lenses of Example 1-1 is shown in Table 3.

[0302] <Manufacturing and evaluation of contact lenses made from a hydrophilic polymer containing methacrylic acid and a contact lens substrate using epoxy-containing organosilicon macromonomers>

[0303] [Examples 1-2]

[0304] The hydrophilicity, lubricity, and anti-lipid adhesion of the contact lens substrate synthesized in Synthesis Example 3-2 were evaluated. The WBUT score was "1", the lubricity score was "1", and the anti-lipid adhesion score was "1".

[0305] The hydrophilic polymer containing methacrylic acid prepared in Synthesis Examples 1-2 was dissolved in water to prepare a 1% hydrophilic polymer solution.

[0306] The contact lens substrate synthesized in Synthesis Example 3-2 and 5.00 g of the prepared hydrophilic polymer solution were placed in a glass bottle. The glass bottle was sealed, and the mixture was subjected to a pressure heat treatment at 121°C for 20 minutes to manufacture contact lenses.

[0307] After pressure heat treatment, the contact lenses are removed and rinsed with 10g of physiological saline. Next, the rinsed contact lenses are placed in a glass bottle, 10g of physiological saline is added, and the bottle is sealed tightly. The bottle is then pressure heat treated at 121°C for 20 minutes, thereby obtaining contact lenses in which the hydrophilic polymer is coated onto the contact lens substrate via covalent bonds of formula (B-1) or (B-2).

[0308] The hydrophilicity, lubricity, and anti-lipid adhesion of the obtained contact lenses were evaluated. The WBUT score was "2", the lubricity score was "2", and the anti-lipid adhesion score was "2".

[0309] The evaluation of the contact lenses of Examples 1-2 is shown in Table 3.

[0310] <Manufacturing and evaluation of contact lenses made from hydrophilic polymers containing 2-aminoethyl methacrylate or methacrylic acid and various contact lens substrates using epoxy-containing organosilicon macromonomers>

[0311] [Examples 1-3 to Examples 1-9]

[0312] The hydrophilic polymer prepared in Synthesis Example 1-1 or Synthesis Example 1-2 was combined with the contact lens substrate synthesized in Synthesis Examples 3-3 to 3-8, and the contact lenses of Examples 1-3 to 1-9 were manufactured in the same manner as in Examples 1-1 or 1-2.

[0313] In addition, the evaluation of the hydrophilicity, lubricity, and anti-lipid adhesion of the contact lens substrate surface in each synthesis example is as follows.

[0314]

[0315] The evaluation of the contact lenses of Examples 1-3 to Examples 1-9 is shown in Table 3.

[0316] <Manufacturing and evaluation of contact lenses made from polymers without reactive monomers and contact lens substrates using epoxy-containing organosilicon macromonomers>

[0317] [Comparative Example 1]

[0318] The hydrophilicity, lubricity, and anti-lipid adhesion of the contact lens substrate synthesized in Synthesis Example 3-1 were evaluated. The WBUT score was "1", the lubricity score was "0", and the anti-lipid adhesion score was "1".

[0319] The polymers without reactive monomers prepared in Synthesis Examples 1-3 were dissolved in water to prepare a 1% polymer solution.

[0320] The contact lens substrate synthesized in Synthesis Example 3-1 and 5.00 g of the prepared polymer solution were placed in a glass bottle, and 0.03 g of sodium hydroxide (NaOH) was added as a catalyst. The glass bottle was sealed, and the mixture was subjected to a pressure heat treatment at 121°C for 20 minutes to manufacture contact lenses.

[0321] After heat treatment, remove the contact lenses and rinse them with 10g of saline solution. Next, place the rinsed contact lenses into a glass bottle, add 10g of saline solution, seal the bottle tightly, and heat treat at 121°C for 20 minutes to manufacture the contact lenses.

[0322] The hydrophilicity, lubricity, and anti-lipid adhesion of the obtained contact lenses were evaluated. The WBUT score was "1", the lubricity score was "0", and the anti-lipid adhesion score was "1".

[0323] The evaluation of the contact lenses of Comparative Example 1 is shown in Table 3.

[0324] <Manufacturing and evaluation of contact lenses made from a hydrophilic polymer containing 2-aminoethyl methacrylate and a contact lens substrate using an epoxy-free organosilicon macromonomer>

[0325] [Comparative Example 2]

[0326] The hydrophilicity, lubricity, and anti-lipid adhesion properties of the contact lens substrates synthesized in Examples 3-10 were evaluated. The WBUT score was "0", the lubricity score was "0", and the anti-lipid adhesion score was "0".

[0327] The hydrophilic polymer containing 2-aminoethyl methacrylate prepared in Synthesis Example 1-1 was dissolved in water to prepare a 1% hydrophilic polymer solution.

[0328] The contact lens substrate synthesized in Synthesis Examples 3-10 and 5.00 g of the prepared hydrophilic polymer solution were placed in a glass bottle, and 0.03 g of sodium hydroxide (NaOH) was added as a catalyst. The glass bottle was sealed, and the mixture was subjected to a pressure heat treatment at 121°C for 20 minutes to manufacture contact lenses.

[0329] After heat treatment, remove the contact lenses and rinse them with 10g of saline solution. Next, place the rinsed contact lenses into a glass bottle, add 10g of saline solution, seal the bottle tightly, and heat treat at 121°C for 20 minutes to manufacture the contact lenses.

[0330] The hydrophilicity, lubricity, and anti-lipid adhesion of the obtained contact lenses were evaluated. The WBUT score was "0", the lubricity score was "0", and the anti-lipid adhesion score was "0".

[0331] The evaluation of the contact lenses of Comparative Example 2 is shown in Table 3.

[0332] <Manufacturing and evaluation of contact lenses made from a hydrophilic polymer containing methacrylic acid and a contact lens substrate using epoxy-free organosilicon macromonomers>

[0333] [Comparative Example 3]

[0334] The hydrophilicity, lubricity, and anti-lipid adhesion of the contact lens substrate synthesized in Synthesis Examples 3-11 were evaluated. The WBUT score was "0", the lubricity score was "0", and the anti-lipid adhesion score was "0".

[0335] The hydrophilic polymer containing methacrylic acid prepared in Synthesis Examples 1-2 was dissolved in water to prepare a 1% hydrophilic polymer solution.

[0336] The contact lens substrate synthesized in Synthesis Example 3-11 and 5.00 g of the prepared hydrophilic polymer solution were placed in a glass bottle. The glass bottle was sealed and subjected to a pressure heat treatment at 121°C for 20 minutes to manufacture contact lenses.

[0337] After heat treatment, remove the contact lenses and rinse them with 10g of saline solution. Next, place the rinsed contact lenses into a glass bottle, add 10g of saline solution, seal the bottle tightly, and heat treat at 121°C for 20 minutes to manufacture the contact lenses.

[0338] The hydrophilicity, lubricity, and anti-lipid adhesion of the obtained contact lenses were evaluated. The WBUT score was "0", the lubricity score was "0", and the anti-lipid adhesion score was "0".

[0339] The manufacturing results of the contact lenses of Comparative Example 3 are shown in Table 3.

[0340] In all evaluation items of WBUT, lubricity, and anti-lipid adhesion, the scores of the contact lenses manufactured in Examples 1-1 to 1-9 were improved compared to the evaluation items of the contact lens substrate used in the manufacturing. Since the scores of WBUT, lubricity, and anti-lipid adhesion of the contact lenses manufactured in Examples 1-1 to 1-9 were all "1" to "2", it shows that the contact lenses obtained by coating a hydrophilic polymer containing 2-aminoethyl methacrylate or methacrylic acid with a contact lens substrate containing an epoxy-containing organosilicon macromonomer through covalent bonding have excellent hydrophilicity, lubricity, and anti-lipid adhesion.

[0341] In the evaluation items of WBUT, lubricity, and anti-lipid adhesion, the scores of the contact lenses manufactured in Comparative Examples 1 to 3 were not improved compared with the evaluation items of the contact lens substrate used in the manufacturing. Since the scores of WBUT, lubricity, and anti-lipid adhesion were "0" to "1", they did not simultaneously exhibit excellent hydrophilicity, lubricity, and anti-lipid adhesion.

[0342] As can be seen from the above, the contact lenses of the present invention simultaneously possess hydrophilicity, lubricity, and anti-lipid adhesion properties.

[0343] [Table 1-1]

[0344]

[0345] [Table 1-2]

[0346]

[0347] [Table 2-1]

[0348]

[0349] [Table 2-2]

[0350]

[0351] [Table 3-1]

[0352]

[0353] [Table 3-2]

[0354]

[0355] Industrial applicability

[0356] This invention provides a contact lens that is hydrophilic, lubricating, and anti-lipid adhesion.

Claims

1. A contact lens comprising a hydrophilic polymer and a contact lens substrate, characterized in that, The hydrophilic polymer is a polymer containing a structural monomer based on at least one of 2-aminoethyl methacrylate or methacrylic acid. The contact lens substrate is a substrate having structural units based on the epoxy-containing organosilicon macromonomer shown in formula (1) below. The hydrophilic polymer is bonded to the contact lens substrate via at least one covalent bond selected from the group consisting of formulas (A-1) to (B-2) below. [Chemical Formula 1] In equation (1), a is an integer from 10 to 500, b is an integer from 1 to 100, and R 1 and R 2 Each can be used independently to represent a hydrogen atom or a methyl group; R 3 and R 4 Each is independently an alkylene divalent group having 2 to 6 carbon atoms or a -R group. 5 -OR 6 - a divalent group, wherein R 5 and R 6 Each of the above is an alkylene divalent group with 2 to 6 carbon atoms, X 0 As shown in equation (2) or equation (3) below, [Chemical Formula 2] In equation (2), R 7 It is an alkylene divalent group with 2 to 8 carbon atoms or -R 9 -OR 10 - a divalent group, wherein R 9 and R 10 Each is an alkylene divalent group with 1 to 6 carbon atoms, independent of the others; R 8 Indicates a hydrogen atom or a methyl group. [Chemical Formula 3] In equation (3), R 11 It is an alkylene divalent group with 2 to 8 carbon atoms or -R 12 -OR 13 - a divalent group, wherein R 12 and R 13 Each of them is an alkylene divalent group with 1 to 6 carbon atoms. [Chemical Formula 4] 2. A method for manufacturing a contact lens, characterized in that, The manufacturing method includes a step of contacting a hydrophilic polymer with a contact lens substrate. The hydrophilic polymer is a polymer containing a structural monomer based on at least one of 2-aminoethyl methacrylate or methacrylic acid. The contact lens substrate is a substrate having structural units based on the epoxy-containing organosilicon macromonomer shown in formula (1) below. In this process, at least one covalent bond is formed from the group consisting of the following formulas (A-1) to (B-2). [Chemical Formula 5] In equation (1), a is an integer from 10 to 500, and b is an integer from 1 to 100; R 1 and R 2 Each can be used independently to represent a hydrogen atom or a methyl group; R 3 and R 4 Each is independently an alkylene divalent group having 2 to 6 carbon atoms or a -R group. 5 -OR 6 - a divalent group, wherein R 5 and R 6 Each is an alkylene divalent group with 2 to 6 carbon atoms, independent of the others; X 0 As shown in equation (2) or equation (3) below, [Chemical Formula 6] In equation (2), R 7 It is an alkylene divalent group with 2 to 8 carbon atoms or -R 9 -OR 10 - a divalent group, wherein R 9 and R 10 Each is an alkylene divalent group with 1 to 6 carbon atoms, independent of the others; R 8 Indicates a hydrogen atom or a methyl group. [Chemical Formula 7] In equation (3), R 11 It is an alkylene divalent group with 2 to 8 carbon atoms or -R 12 -OR 13 - a divalent group, wherein R 12 and R 13 Each of them is an alkylene divalent group with 1 to 6 carbon atoms. [Chemical Formula 8] 3. The contact lens according to claim 1, wherein, The hydrophilic polymer is a copolymer containing structural monomers based on the monomers shown in formula (4) below. [Chemical Formula 9] In equation (4), R 14 It represents a hydrogen atom or a methyl group.

4. The method for manufacturing a contact lens according to claim 2, wherein, The hydrophilic polymer is a copolymer containing structural monomers based on the monomers shown in formula (4) below. [Chemical Formula 10] In equation (4), R 14 It represents a hydrogen atom or a methyl group.

5. A contact lens substrate containing structural units based on an epoxy-containing organosilicon macromonomer as shown in formula (1), [Chemical Formula 11] In equation (1), a is an integer from 10 to 500, and b is an integer from 1 to 100; R 1 and R 2 Each can be used independently to represent a hydrogen atom or a methyl group; R 3 and R 4 Each is independently an alkylene divalent group having 2 to 6 carbon atoms or a -R group. 5 -OR 6 - a divalent group, wherein R 5 and R 6 Each is an alkylene divalent group with 2 to 6 carbon atoms, independent of the others; X 0 As shown in equation (2) or equation (3) below, [Chemical Formula 12] In equation (2), R 7 It is an alkylene divalent group with 2 to 8 carbon atoms or -R 9 -OR 10 - a divalent group, wherein R 9 and R 10 Each is an alkylene divalent group with 1 to 6 carbon atoms, independent of the others; R 8 Indicates a hydrogen atom or a methyl group. [Chemical Formula 13] In equation (3), R 11 It is an alkylene divalent group with 2 to 8 carbon atoms or -R 12 -OR 13 - a divalent group, wherein R 12 and R 13 Each of them is an alkylene divalent group with 1 to 6 carbon atoms, which are independent of each other.

6. The contact lens according to claim 1 or 3, wherein, The hydrophilic polymer is a polymer containing a structural monomer based on 2-aminoethyl methacrylate, and for the epoxy-containing organosilicon macromonomer shown in formula (1), in formula (1), a is an integer from 30 to 280, b is an integer from 1 to 70, and R 1 For -CH3, R 2 For -CH3, R 3 For -CH2CH2CH2-, R 4 For -CH2CH2CH2-, X 0 For equation (2), in equation (2), R 7 For -CH2CH2CH2-O-CH2- or -CH2CH2CH2-, R 8 It is -H.

7. The contact lens according to claim 1 or 3, wherein, The hydrophilic polymer is a polymer containing a methacrylic acid-based structural monomer, and for the epoxy-containing organosilicon macromonomer shown in formula (1), in formula (1), a is an integer from 30 to 280, b is an integer from 1 to 70, and R 1 For -CH3, R 2 For -CH3, R 3 For -CH2CH2CH2-, R 4 For -CH2CH2CH2-, X 0 For equation (2), in equation (2), R 7 For -CH2CH2CH2-O-CH2- or -CH2CH2CH2-, R 8 It is -H.

8. The contact lens according to claim 1 or 3, wherein, The hydrophilic polymer is a polymer containing a methacrylic acid-based structural monomer, and for the epoxy-containing organosilicon macromonomer shown in formula (1), in formula (1), a is an integer from 30 to 280, b is an integer from 1 to 70, and R 1 For -CH3, R 2 For -CH3, R 3 For -CH2CH2CH2-, R 4 For -CH2CH2CH2-, X 0 For equation (3), in equation (3), R 11 It is -CH2CH2-.

9. The contact lens according to claim 1 or 3, wherein, The hydrophilic polymer is a polymer containing a structural monomer based on 2-aminoethyl methacrylate, and for the epoxy-containing organosilicon macromonomer shown in formula (1), in formula (1), a is an integer from 30 to 280, b is an integer from 1 to 70, and R 1 For -CH3, R 2 For -CH3, R 3 For -CH2CH2CH2-, R 4 For -CH2CH2CH2-, X 0 For equation (3), in equation (3), R 11 It is -CH2CH2-.

10. The method for manufacturing a contact lens according to claim 2 or 4, wherein, The hydrophilic polymer is a polymer containing a structural monomer based on 2-aminoethyl methacrylate, and for the epoxy-containing organosilicon macromonomer shown in formula (1), in formula (1), a is an integer from 30 to 280, b is an integer from 1 to 70, and R 1 For -CH3, R 2 For -CH3, R 3 For -CH2CH2CH2-, R 4 For -CH2CH2CH2-, X 0 For equation (2), in equation (2), R 7 For -CH2CH2CH2-O-CH2- or -CH2CH2CH2-, R 8 It is -H.

11. The method for manufacturing a contact lens according to claim 2 or 4, wherein, The hydrophilic polymer is a polymer containing a methacrylic acid-based structural monomer, and for the epoxy-containing organosilicon macromonomer shown in formula (1), in formula (1), a is an integer from 30 to 280, b is an integer from 1 to 70, and R 1 For -CH3, R 2 For -CH3, R 3 For -CH2CH2CH2-, R 4 For -CH2CH2CH2-, X 0 For equation (2), in equation (2), R 7 For -CH2CH2CH2-O-CH2- or -CH2CH2CH2-, R 8 It is -H.

12. The method for manufacturing a contact lens according to claim 2 or 4, wherein, The hydrophilic polymer is a polymer containing a methacrylic acid-based structural monomer, and for the epoxy-containing organosilicon macromonomer shown in formula (1), in formula (1), a is an integer from 30 to 280, b is an integer from 1 to 70, and R 1 For -CH3, R 2 For -CH3, R 3 For -CH2CH2CH2-, R 4 For -CH2CH2CH2-, X 0 For equation (3), in equation (3), R 11 It is -CH2CH2-.

13. The method for manufacturing a contact lens according to claim 2 or 4, wherein, The hydrophilic polymer is a polymer containing a structural monomer based on 2-aminoethyl methacrylate, and for the epoxy-containing organosilicon macromonomer shown in formula (1), in formula (1), a is an integer from 30 to 280, b is an integer from 1 to 70, and R 1 For -CH3, R 2 For -CH3, R 3 For -CH2CH2CH2-, R 4 For -CH2CH2CH2-, X 0 For equation (3), in equation (3), R 11 It is -CH2CH2-.

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