Method for manufacturing hybrid contact lens containing hydrophobic member

Abstract

The purpose of the present invention is to provide a method for manufacturing a hybrid contact lens containing a hydrophobic member that is a material having different properties from those of a contact lens base material, the method including specific procedures and having smaller degree of influence on the optical characteristics of the contact lens. The purpose is achieved by, for example, a method including: a step for subjecting a mold in which a male mold having a hydrophobic member placed on the top surface of a protruded portion thereof is mated with a female mold having a first contact lens formation composition in a recessed portion thereof to a first copolymerization reaction to produce a first copolymer having the hydrophobic member; a step for subjecting the mold in which the female mold containing a second contact lens formation composition on the first copolymer in the recessed portion is mated with the male mold to a second copolymerization reaction to produce a second copolymer having the hydrophobic member contained therein; and a step for swelling the second copolymer by hydration to produce a hybrid contact lens containing the hydrophobic member therein.

Description

Method for manufacturing a hybrid contact lens containing a hydrophobic component

[0001] The present invention relates to a method for making a hybrid contact lens containing a hydrophobic component.

[0002] Contact lenses are used as devices for correcting vision. In recent years, contact lenses have been developed that combine their original function of correcting vision with new functions, such as information display devices with displays that project text and images, and measuring devices for testing biological functions.

[0003] Contact lenses such as information display devices and measuring devices are formed by embedding components for realizing new functions inside the contact lens substrate. Known contact lenses include hybrid multifocal contact lenses obtained by incorporating a hard lens material into a soft lens material (see, for example, Patent Document 1), and silicone elastomer-hydrogel hybrid contact lenses obtained by bonding a silicone elastomer layer and a hydrogel layer with a peel-resistant bond (see, for example, Patent Document 2).

[0004] Special table 2006-515689 publication Special table 2019-515326 publication

[0005] When a contact lens substrate contains a component made of a material with different properties from the substrate, for example, when a hydrophobic component is contained within a hydrogel, the adhesion between the contact lens substrate and the contained hydrophobic component has a significant impact on the safety of wearing the lens. That is, if the adhesion between the contact lens substrate and the contained hydrophobic component is poor, there is a risk that the contact lens substrate will break during wear, and the exposed hydrophobic component will damage ocular tissue. Furthermore, in this case, there is a concern that the optical properties of the contact lens will be adversely affected.

[0006] The contact lens described in Patent Document 1 is a hybrid multifocal contact lens made of a soft lens material containing a hard lens material, but Patent Document 1 does not specifically disclose a manufacturing method for the contact lens. Therefore, the contact lens described in Patent Document 1 has the problem that it cannot be manufactured according to a specific procedure.

[0007] The contact lens described in Patent Document 2 is a hybrid contact lens formed by bonding a silicone elastomer layer and a hydrogel layer, and is obtained by penetrating a portion of a hydrogel material into the silicone elastomer and adhering the two together. However, in the method described in Patent Document 2, the hydrogel material that has penetrated into the silicone elastomer hydrates during the hydration swelling step, allowing moisture to penetrate into the silicone elastomer. As a result, this method has the problem of causing the silicone elastomer to become cloudy, resulting in deterioration of optical properties.

[0008] There are few known methods for manufacturing hybrid contact lenses that incorporate components, particularly hydrophobic components, made of materials with properties different from those of the contact lens substrate, and that involve specific procedures while minimizing the impact on the optical properties of the hybrid contact lens.

[0009] Therefore, the problem that the present invention aims to solve is to provide a method for producing a contact lens containing a hydrophobic member, which is a material with properties different from those of the contact lens substrate, with specific procedures and little effect on the optical properties of the hybrid contact lens.

[0010] In order to solve the above problems, the present inventors have conducted extensive research into a method for producing a contact lens that has little effect on optical properties by maintaining good adhesion between the hydrophobic material to be contained and the contact lens substrate. As a result, they have come to the conclusion that if the hydrophobic material has polymerizable functional groups on its surface that serve as bonding points with the contact lens substrate, it may be possible to chemically bond the hydrophobic material to the contact lens substrate.

[0011] Then, after further trial and error, the inventors surprisingly found that when they tried a method in which a hydrophobic material treated with a silane coupling agent whose organic functional group is a polymerizable functional group was brought into contact with a monomer composition for contact lens substrates twice, and each time subjected to a copolymerization reaction, the encapsulated hydrophobic material and the contact lens substrate were firmly adhered together even after hydration and swelling.

[0012] Based on these findings, the present inventors have finally succeeded in creating a method for producing a hybrid contact lens, which can solve the problems of the present invention, by subjecting a hydrophobic material having polymerizable functional groups on its surface and a monomer solution for a contact lens substrate to a copolymerization reaction in two separate steps. The present invention was completed based on the findings first discovered by the present inventors and the successful examples they have achieved.

[0013] That is, the present invention provides the following aspects: [1] A method for producing a hybrid contact lens containing a hydrophobic member, comprising: a step of: subjecting a molding die, which is made by fitting a male mold having a hydrophobic member having polymerizable functional groups on its surface onto the top faces of its convex parts with a female mold containing a first contact lens-forming composition in its concave parts, to a first copolymerization reaction to obtain a first copolymer having the hydrophobic member from the surface in contact with the male mold to its interior; a step of subjecting a molding die, which is made by fitting a female mold having a second contact lens-forming composition on top of the first copolymer in its concave parts with the male mold, to a second copolymerization reaction to obtain a second copolymer having the hydrophobic member inside; and a step of subjecting the second copolymer to a hydration swelling treatment to obtain a hybrid contact lens containing a hydrophobic member. [2] A method for producing a hybrid contact lens containing a hydrophobic member, comprising: a step of placing a hydrophobic member having polymerizable functional groups on the bottom of a recess, and fitting a female mold containing a first contact lens composition in the recess with a male mold, and subjecting the resulting mold to a first copolymerization reaction to obtain a first copolymer having the hydrophobic member extending from the surface in contact with the female mold to the interior, a step of fitting a female mold containing a second contact lens composition in the recess with a male mold having the first copolymer on the top surface of the convex portion, and subjecting the second copolymer to a hydration swelling treatment to obtain a hybrid contact lens containing a hydrophobic member. [3] A method for producing a hybrid contact lens according to item [1] or [2], further comprising a step of treating the hydrophobic member with a silane coupling agent whose organic functional group is a polymerizable functional group to obtain a hydrophobic member having polymerizable functional groups on the surface. [4] The method for manufacturing a hybrid contact lens according to any one of items [1] to [3], wherein the hydrophobic member is a hydrophobic member selected from the group consisting of a thermoplastic elastomer, a thermosetting elastomer, a thermosetting polymer, and a thermoplastic polymer. [5] The method for manufacturing a hybrid contact lens according to any one of items [1] to [4], wherein the hydrophobic member is a hydrophobic member having through holes.[6] A hybrid contact lens obtained by the manufacturing method according to any one of items [1] to [5].

[0014] According to the present invention, a hybrid contact lens incorporating a hydrophobic material can be produced using a specific procedure with minimal impact on the optical properties of the contact lens. Specifically, according to the present invention, the incorporated hydrophobic material is chemically bonded to the contact lens substrate, resulting in a hybrid contact lens in which the hydrophobic material is hardly separated from the contact lens substrate even when the hydrogel substrate is in a hydrated and swollen state. Therefore, according to the present invention, damage to ocular tissues and impairment of the optical properties of the contact lens caused by exposure of the incorporated hydrophobic material during contact lens wear can be prevented.

[0015] According to the present invention, the transparency of a contact lens is maintained even after hydration and swelling, and therefore it is possible to use the contact lens for vision correction, which is the original function of a contact lens, while also combining functions based on the hydrophobic material contained therein, and it is expected that the lens will be used as a new type of contact lens.

[0016] Figure 1A is a schematic diagram of a method for manufacturing a hybrid contact lens according to a first embodiment of the present invention. Figure 1B is a schematic diagram of a method for manufacturing a hybrid contact lens according to a second embodiment of the present invention. Figure 2 is an enlarged cross-sectional photograph of the hybrid contact lens of Example 1, as described in the Examples below. Figure 3 is an enlarged plan view photograph of the hybrid contact lens of Example 1, as described in the Examples below. Figure 4 is an enlarged plan view photograph of the hybrid contact lens of Reference Example 1, as described in the Examples below.

[0017] Each aspect of the present invention will be described in detail below, but the present invention can take various forms as long as the object of the present invention is achieved.

[0018] Unless otherwise specified, the terms used in this specification are used in the sense commonly used by those skilled in the chemical industry dealing with contact lenses, and should not be construed as having an unduly limiting meaning. Furthermore, the speculations and theories made in this specification are based on the knowledge and experience of the inventors to date, and therefore the present invention is not limited solely to such speculations and theories.

[0019] The term "and / or" means any one of the listed related items, or any or all combinations of two or more. "Comprising" means that elements other than those explicitly stated as being included can be added (same meaning as "comprising at least"), but also encompasses "consisting of" and "consisting essentially of." That is, "comprising" can mean including the explicitly stated elements and any one or more elements, consisting of the explicitly stated elements, or consisting essentially of the explicitly stated elements. Elements include limitations such as components, steps, conditions, parameters, etc. "(Meth)acrylate" is a general term for acrylate and methacrylate. The same applies to a (meth)acryloyl group.

[0020] [Summary of the Method of the Present Invention] According to one aspect of the present invention, there is provided a method for producing a hybrid contact lens comprising a contact lens substrate containing a hydrophobic material chemically bonded thereto. The method of one aspect of the present invention can be broadly divided into two specific embodiments.

[0021] The method of the first aspect of the present invention comprises the following steps (1) to (3): (1) a step of fitting a male mold having a hydrophobic member having polymerizable functional groups on the top surface of a convex portion thereof with a female mold containing a first contact lens-forming composition in a concave portion thereof, and subjecting the fitting to a first copolymerization reaction to obtain a first copolymer having the hydrophobic member from the surface in contact with the male mold to the interior thereof; (2) a step of fitting a male mold having a female mold containing a second contact lens-forming composition on the first copolymer in a concave portion thereof with the male mold, and subjecting the fitting to a second copolymerization reaction to obtain a second copolymer having the hydrophobic member inside; and (3) a step of subjecting the second copolymer to a hydration swelling treatment to obtain a hybrid contact lens containing a hydrophobic member.

[0022] The method of the second aspect of the present invention comprises the following steps (1)' to (3): (1)' a step of placing a hydrophobic member having a polymerizable functional group on the bottom surface of a recess, and fitting a female mold containing a first contact lens-forming composition into the recess with a male mold, and subjecting the resulting mold to a first copolymerization reaction to obtain a first copolymer having the hydrophobic member from the surface in contact with the female mold to the interior; (2)' a step of fitting a female mold containing a second contact lens-forming composition in the recess with a male mold having the first copolymer on the top surface of the convex portion, and subjecting the resulting mold to a second copolymerization reaction to obtain a second copolymer having the hydrophobic member inside; and (3)' a step of subjecting the second copolymer to a hydration swelling treatment to obtain a hybrid contact lens containing a hydrophobic member.

[0023] [Outline of the method of the first aspect of the present invention] Referring to FIG. 1A, a hybrid contact lens 10 obtained by the method of the first aspect of the present invention is made by incorporating a hydrophobic material 12 into a hydrogel contact lens substrate 11 via a chemical bond.

[0024] In the method of the first aspect of the present invention, a molding die is formed by fitting together a male mold 1 having a hydrophobic material 12, the surface of which has been modified with a polymerizable functional group, placed on the top face of the convex portion, and a female mold 2 having a first contact lens-forming composition 101 poured into its concave portion, and the resulting integrated molding die is subjected to a first copolymerization reaction to obtain a first copolymer 121 having a hydrophobic material 12 extending from the surface in contact with the male mold 1 to the interior. When the molding die is separated, the first copolymer 121 is found to be placed in the concave portion of the female mold 2.

[0025] Next, the female mold 2 containing the second contact lens forming composition 102 injected into the recess from above the first copolymer 121 is fitted together with the male mold 3 to form an integrated mold, and the mold is subjected to a second copolymerization reaction to obtain a second copolymer 122 having (encompassing) the hydrophobic member 12 therein.

[0026] Next, the second copolymer 122 is hydrated and swollen to obtain a hybrid contact lens 10 containing a hydrophobic member 12. The hybrid contact lens obtained by the method of the first aspect of the present invention has excellent functions exhibited by the hydrophobic member, such as oxygen permeability, due to the hydrophobic member contained therein, compared to a hybrid contact lens that does not contain a hydrophobic member.

[0027] [Outline of the method of the second aspect of the present invention] Referring to Figure 1B, the hybrid contact lens 10 obtained by the method of the second aspect of the present invention is made by incorporating a hydrophobic material 12 into a hydrogel contact lens substrate 11 via a chemical bond.

[0028] In the method of the second aspect of the present invention, a hydrophobic member 12 whose surface has been modified with a polymerizable functional group is placed on the bottom surface of a recess, and a female mold 2 containing a first contact lens-forming composition 101 poured into the recess is fitted into a male mold 1 to form an integrated mold, which is then subjected to a first copolymerization reaction to obtain a first copolymer 121 having a hydrophobic member 12 extending from the surface in contact with the female mold 2 to the interior. When the mold is separated, first copolymer 121 is found to be attached to the top surface of the convex portion of male mold 1.

[0029] Next, the female mold 4 containing the second contact lens-forming composition 102 injected into the recessed portion and the male mold 1 having the first copolymer 121 on the top surface of the convex portion are fitted together to form an integrated mold, which is then subjected to a second copolymerization reaction to obtain a second copolymer 122 having (encompassing) the hydrophobic member 12 therein.

[0030] Next, the second copolymer 122 is hydrated and swollen to obtain a hybrid contact lens 10 containing a hydrophobic member 12. The hybrid contact lens obtained by the method of the second aspect of the present invention is superior in the functions exhibited by the hydrophobic member, such as oxygen permeability, due to the hydrophobic member contained therein, compared to a hybrid contact lens that does not contain a hydrophobic member.

[0031] [Steps (1) and (1)' for Obtaining the First Copolymer] In step (1), a hydrophobic material having polymerizable functional groups on its surface is placed on the top surface of the convex portion of the male mold. In step (1)', a hydrophobic material having polymerizable functional groups on its surface is placed on the bottom surface of the concave portion of the female mold.

[0032] The hydrophobic material may be any material having the desired function to be imparted to the contact lens, and examples thereof include thermoplastic elastomers classified as styrene-based, olefin-based, ester-based, urethane-based, etc.; thermosetting elastomers classified as silicone-based, fluorine-based, urethane-based, etc.; thermosetting polymeric compounds containing silicone or the like in the molecule; and thermoplastic polymeric compounds such as polyethylene, polyolefin, PET, etc. From the viewpoint of the function to be imparted to the resulting hybrid contact lens, particularly oxygen permeability, silicone-based elastomers and silicone-containing polymeric compounds are preferred as the hydrophobic material.

[0033] The method for obtaining the hydrophobic member may be appropriately selected depending on the material of the hydrophobic member. For example, LIM molding is preferably used for silicone-based elastomers, and cast molding is preferably used for silicone-containing polymer compounds. In either molding method, it is preferable to use a pair of molds consisting of a female mold with a recessed portion molded to the desired shape and a male mold with a protruding portion. For example, the hydrophobic member can be formed by injecting a raw material composition for the hydrophobic member into the recessed portion of the female mold, and then subjecting the mold formed by fitting the female mold and the male mold together to a treatment under conditions that allow the raw material composition to react, such as heating or light irradiation.

[0034] Examples of raw material compositions for the hydrophobic material include commercially available raw material compositions for silicone elastomers and raw material compositions containing hydrophobic monomers such as silicone-containing monomers described below. Examples of commercially available raw material compositions include those described in the Examples described below. However, although some components of the raw material composition for the hydrophobic material may be common to some components of the composition for forming a contact lens described below, the raw material composition for the hydrophobic material as a whole is different from the composition for forming a contact lens, and therefore the hydrophobic material is different from a contact lens substrate.

[0035] The raw material composition for the hydrophobic material may further contain a polymerization initiator. When the raw material composition for the hydrophobic material contains a polymerization initiator, the polymerization initiator is introduced into the surface and / or interior of the resulting hydrophobic material, thereby improving the reactivity of the first and second copolymerization reactions carried out in the method of one embodiment of the present invention. The polymerization initiator may be one described below.

[0036] The hydrophobic material may be processed and / or modified depending on the desired properties to be imparted to the contact lens. For example, in order to exhibit excellent oxygen permeability and vision correction function, the hydrophobic material preferably has one or more through holes.

[0037] The hydrophobic member has polymerizable functional groups on its surface. The method for modifying the surface of the hydrophobic member with the polymerizable functional groups is preferably a method for orienting the polymerizable functional groups on the surface of the hydrophobic member so that they can copolymerize with the polymerizable functional groups of the contact lens-forming monomer in contact with the hydrophobic member. Specifically, the method for modifying the surface of the hydrophobic member with the polymerizable functional groups is preferably a method for reacting the hydrophobic member with a silane coupling agent whose organic functional group is a polymerizable functional group, since this method efficiently orients the polymerizable functional groups on the surface of the hydrophobic member. Note that when the method for modifying the surface of the hydrophobic member with the polymerizable functional groups involves irradiating the hydrophobic member with oxygen plasma and then reacting it with a (meth)acrylic compound containing an isocyanate, peeling occurs between the hydrophobic member and the contact lens substrate, resulting in poor adhesion.

[0038] The silane coupling agent may be any agent having a structure in which one end is a hydrolyzable group that serves as a bonding site with the hydrophobic material, and the other end is an organic functional group that is a polymerizable functional group such as an allyl group, a vinyl group, an acryloyl group, a methacryloyl group, a styrenyl group, etc., that bonds with a polymerizable functional group of a contact lens-forming monomer via a free radical reaction. Examples of such silane coupling agents include 3-(meth)acryloxypropyltrimethoxysilane, trimethoxy(7-octen-1-yl)silane, and N-[2-(N-vinylbenzylamino)ethyl]-3-aminopropyltrimethoxysilane hydrochloride, with 3-methacryloyloxypropyltrimethoxysilane being preferred from the viewpoints of ease of handling and reactivity.

[0039] A hydrophobic material having polymerizable functional groups on its surface can be obtained by treating the hydrophobic material with a silane coupling agent whose organic functional group is a polymerizable functional group. Examples of methods for treating a hydrophobic material with a silane coupling agent include common methods such as immersing the hydrophobic material in an aqueous solution containing the silane coupling agent and subjecting it to a heating treatment. To improve reactivity, the aqueous solution containing the silane coupling agent may contain an acid such as acetic acid or a nonionic surfactant such as a polyoxyethylene polyoxypropylene block polymer. To improve the affinity of the hydrophobic material with the aqueous solution and effectively introduce polymerizable functional groups, it is preferable to subject the surface of the hydrophobic material to an activation treatment such as plasma irradiation in advance.

[0040] By carrying out such a step, the surface of the hydrophobic material can be modified with a polymerizable functional group. Preferably, the method of one aspect of the present invention further includes, prior to step (1) and step (1)', a step of treating the hydrophobic material with a silane coupling agent whose organic functional group is a polymerizable functional group, thereby obtaining a hydrophobic material having a polymerizable functional group on its surface.

[0041] The method for placing the hydrophobic material having polymerizable functional groups on its surface on the top surface of the convex portion of the male mold or the bottom surface of the concave portion of the female mold is not particularly limited, but for example, the hydrophobic material having polymerizable functional groups on its surface may be held with tweezers or the like and placed on the top surface of the convex portion of the male mold or the bottom surface of the concave portion of the female mold.

[0042] In steps (1) and (1)', the first contact lens-forming composition is poured into the recess of the female mold so as to contain the first contact lens-forming composition. In step (1)', the first contact lens-forming composition is poured so as to cover the hydrophobic member placed on the bottom surface of the recess.

[0043] The composition for forming a contact lens may be any composition that can be used to form the base material of the hybrid contact lens obtained by the method of one aspect of the present invention. The hybrid contact lens is composed of a hydrogel.

[0044] Hydrogels are based on a polymer of monomer components including hydrophilic monomers. Hydrogels swell within a polymer matrix with an aqueous liquid, such as water or a solution containing water, and retain the aqueous liquid. In this specification, the polymer itself, excluding the aqueous liquid, is referred to as the base material of the hydrogel (contact lens). Polymers are formed by the polymerization of monomers, and the constituent units derived from each monomer in a polymer are also referred to as residues and moieties.

[0045] Specific examples of hydrogels include hydrogels produced using hydrophilic monomers, hydrogels produced using a hydrophilic monomer and a hydrophobic monomer, and a hydrophilic monomer and a copolymerizable monomer such as a crosslinkable monomer.

[0046] Hydrogels have at least hydrophilic monomers as residues. Therefore, the contact lens-forming composition contains a hydrophilic monomer, and may further contain other monomer components such as a hydrophobic monomer copolymerizable with the hydrophilic monomer, a crosslinking monomer, and a polymerization initiator that promotes the copolymerization reaction of the monomers, depending on the properties desired for the contact lens.

[0047] The hydrophilic monomer may be any polymerizable compound having at least one hydrophilic group and a polymerizable group such as a (meth)acryloyl group or a vinyl group in the molecule, and examples thereof include hydroxymethyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2,3-dihydroxypropyl (meth)acrylate, 2-polyethylene glycol mono(meth)acrylate, 2-polypropylene glycol (meth)acrylate, N,N-dimethyl (meth)acrylamide, N,N-diethyl (meth)acrylamide, and N-vinylpyrrolidone, with 2-hydroxyethyl methacrylate being preferred among these. As the hydrophilic monomer, one of these may be used alone, or two or more may be used in combination.

[0048] The content of the hydrophilic monomer may be any amount that allows the polymer obtained by copolymerizing the monomer components containing the hydrophilic monomer to form a hydrogel, and can be set appropriately. For example, the content of the hydrophilic monomer is preferably 50 wt % to 99 wt %, more preferably 60 wt % to 98 wt %, and even more preferably 70 wt % to 96 wt %, relative to the total amount of the monomer components.

[0049] The hydrophobic monomer may be any polymerizable compound that does not have a hydrophilic group in the molecule and has a polymerizable group such as a (meth)acryloyl group or a vinyl group, and examples thereof include (meth)acrylic monomers such as trifluoroethyl methacrylate, methacrylamide, siloxanyl methacrylate, methyl methacrylate, n-butyl methacrylate, tert-butyl methacrylate, benzyl methacrylate, ethylhexyl methacrylate, lauryl (meth)acrylate, and tridecyl methacrylate; α-mono(methacryloyloxymethyl)siloxane, α,ω-di(methacryloxymethyl)polydimethylsiloxane, α-mono(3-methacryloyloxypropyl)polydimethylsiloxane, α,ω-di(3-methacryloyloxypropyl)polydimethylsiloxane, α-mono(3-methacryloyloxybutyl)polydimethylsiloxane, and α,ω-di(3-methacryloyloxymethyl)polydimethylsiloxane. Examples of the monomer include silicone-containing monomers such as octafluoropentyl methacrylate, ...

[0050] The content of the hydrophobic monomer may be appropriately set depending on the desired optical and physicochemical properties of the hydrogel, and is preferably 0 wt% to 20 wt%, and more preferably 1 wt% to 10 wt%, relative to the total amount of the monomer components. If the content of the hydrophobic monomer exceeds 20 wt%, the flexibility of the resulting hydrogel may decrease, which may impair the wearing comfort.

[0051] The crosslinking monomer may be any polymerizable compound having two or more polymerizable groups, such as (meth)acryloyl groups or vinyl groups, in the molecule, such as ethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, methylene bis(meth)acrylamide, 2-hydroxy-1,3-di(meth)acryloxypropane, trimethylolpropane tri(meth)acrylate, etc., with triethylene glycol dimethacrylate being preferred. As the crosslinking monomer, one of these may be used alone, or two or more may be used in combination.

[0052] The content of the crosslinking monomer may be appropriately set depending on the desired network structure formability and mechanical strength of the hydrogel, and is, for example, preferably 0.1 wt % to 10 wt %, and more preferably 1 wt % to 6 wt %, relative to the total amount of the monomer components. If the content of the crosslinking monomer exceeds 10 wt %, the flexibility of the obtained hydrogel may decrease, which may impair the wearing comfort, making it unsuitable for contact lenses.

[0053] The polymerization initiator is used when copolymerizing the monomer components, and may be appropriately selected depending on the properties of the monomers to be blended in the contact lens forming composition. For example, common photopolymerization initiators such as benzophenone, 1-hydroxycyclohexyl phenyl ketone, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl-4'-(methylthio)-2-morpholinopropiophenone, 2-benzyl-2-(dimethylamino)-4'-monofolinobutyrophenone, and diphenyl(2,4,6-trimethylbenzoyl) Examples of suitable photopolymerization initiators include photoradical polymerization initiators such as phosphine oxide and phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide; photocationic polymerization initiators such as bis(4-tertiarybutylphenyl)iodonium hexafluorophosphate, 2-(1,3-benzodioxol-5-yl)-4,6-bis(trichloromethyl)-1,3,5-triazine and (4-hydroxyphenyl)dimethylsulfonium hexafluorophosphate; photoanionic polymerization initiators such as 1,2-dicyclohexyl-4,4,5,5-tetramethylbiguaninium n-butyltriphenylborate; and general thermal polymerization initiators such as peroxide-based polymerization initiators such as lauroyl peroxide, cumene hydroperoxide and benzoyl peroxide; and azo-based polymerization initiators such as azobisdimethylvaleronitrile and azobisisobutyronitrile, but photopolymerization initiators are preferred. These polymerization initiators may be used alone or in combination of two or more.

[0054] The amount of the polymerization initiator to be added may be any amount that can achieve the copolymerization reaction of the monomers, and can be set appropriately, but is preferably 10 ppm to 7,000 ppm, for example, based on the total amount of the monomer components.

[0055] The contact lens forming composition may optionally contain other ingredients known in the art, including, but not limited to, UV absorbers, diluents, stabilizers, dyes, pigments, antimicrobial compounds, mold release agents, etc. Some of the other ingredients are listed below, but these are merely examples and are not intended to be limiting.

[0056] Examples of ultraviolet absorbers include 2-hydroxy-4-(meth)acryloyloxybenzophenone, 2-hydroxy-4-(meth)acryloyloxy-5-t-butylbenzophenone, 2-(2'-hydroxy-5'-(meth)acryloyloxyethylphenyl)-2H-benzotriazole, 2-(2'-hydroxy-5'-(meth)acryloyloxyethylphenyl)-5-chloro-2H-benzotriazole, 2-hydroxy-4-methacryloyloxymethylphenyl benzoate, and 2-[3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl]ethyl methacrylate. The ultraviolet absorber may be any one of these alone or a combination of two or more. The content of the ultraviolet absorber may be set to any amount depending on the desired ultraviolet absorption ability.

[0057] Examples of diluents include water, dimethyl sulfoxide, polyethylene glycol 200, and polyethylene glycol 600. The diluent may be any one of these, or a combination of two or more of these. The content of the diluent may be set to any amount depending on the desired physical properties.

[0058] From the viewpoint of obtaining a desired water content and size of the hydrogel, it is preferable that the monomer mixture and the diluent have a predetermined relationship. For example, the ratio of the monomer mixture to the diluent (monomer mixture:diluent) is preferably 10:0 to 6:4, and more preferably 10:0 to 7:3.

[0059] The contact lens-forming composition can be obtained, for example, by stirring and dissolving a mixture containing the monomer components, the polymerization initiator, and optionally other components in accordance with a conventional method. A specific example of such a method includes a method comprising stirring and mixing a mixture of these components, the amounts of which are set so that the resulting copolymer has the desired physical properties, using a magnetic stirrer or the like.

[0060] In step (1), a female mold containing a first contact lens-forming composition in its recessed portion is fitted with a male mold having a hydrophobic member having polymerizable functional groups on its surface and mounted on the top surface of its convex portion, and the fitting and sealing are performed to obtain a molding die in which the male mold and female mold are integrated. This molding die is subjected to a first copolymerization reaction to obtain a first copolymer having a hydrophobic member extending from its surface in contact with the male mold to its interior. Similarly, in step (1)', a female mold containing a hydrophobic member having polymerizable functional groups and the first contact lens-forming composition in its recessed portion is fitted with the male mold to obtain a molding die in which the male mold and female mold are integrated. This molding die is subjected to a first copolymerization reaction to obtain a first copolymer having a hydrophobic member extending from its surface in contact with the female mold to its interior.

[0061] The first copolymerization reaction is carried out by heating or irradiating a mold containing the first contact lens-forming composition, depending on the type of copolymerization reaction. For example, if the copolymerization reaction utilizes thermal polymerization, the mold may be heated stepwise or continuously within a range of 25°C to 120°C in a thermostatic bath or the like, and the reaction may be carried out for a reaction time of 5 to 120 hours. Alternatively, if the copolymerization reaction utilizes photopolymerization, the copolymerization reaction may be carried out by irradiating the mold with ultraviolet light for 1 minute to 5 hours.

[0062] The molding die consisting of a male mold and a female mold may be one that is normally used in the production of contact lenses. For example, the resin used in the molding die may be any resin that does not dissolve the base material of the contact lens and is inactive to plasma, etc. Specific examples of resins include polyethylene, polypropylene, ethylene-vinyl acetate, polystyrene, AS resin, ABS resin, polymethyl methacrylate, polyvinyl chloride, cellulose-based resin, polyacetal, polyamide, polybutylene terephthalate, polyethylene terephthalate, polycarbonate, modified polyphenylene ether, polyphenylene sulfide, polyether ether ketone, liquid crystal polymer, polysulfone, polyether sulfone, polyarylate, polyamide-imide, polyether-imide, polymethylpentene, phenolic resin, urea resin, melamine resin, and epoxy resin. The resin may consist of one of these resins or a combination of two or more thereof, but polypropylene is preferred from the viewpoint of moldability.

[0063] In consideration of the operational efficiency of step (2), it is preferable that the first copolymer be attached to the female mold after step (1). Similarly, in consideration of the operational efficiency of step (2)', it is preferable that the first copolymer be attached to the male mold after step (1)'. Methods for attaching the first copolymer to the female mold or male mold include a method of physically treating the surface of the concave portion of the female mold or the convex portion of the male mold by corona discharge, plasma irradiation, etc., and a method of preparing a female mold made of a different material from the male mold or a male mold made of a different material from the female mold, taking into consideration the affinity with the contact lens-forming composition.

[0064] Examples of physical surface treatment methods include treating the recessed surfaces of the female mold or the protruding surfaces of the male mold by corona discharge, plasma irradiation, or the like under conditions that increase hydrophilicity. Furthermore, methods for preparing a female mold or a male mold made of a material different from that of the male mold include, for example, preparing a female mold made of a resin that has a higher affinity for the first copolymer than the male mold, or preparing a male mold made of a resin that has a higher affinity for the first copolymer than the female mold. By using such methods, the male mold and the female mold are separated after the first copolymerization reaction, which makes it possible to selectively attach the first copolymer having a hydrophobic member to the recessed surfaces of the female mold after step (1), and to selectively attach the first copolymer having a hydrophobic member to the protruding surfaces of the male mold after step (1)'.

[0065] [Steps (2) and (2)' for Obtaining a Second Copolymer] In step (2), a female mold containing the first copolymer obtained in step (1) is prepared by injecting a second contact lens-forming composition into the recess of the female mold so that the first copolymer is covered, and the female mold is then fitted with a male mold. In step (2)', a female mold containing the second contact lens-forming composition is prepared and fitted with the male mold containing the first copolymer obtained in step (1)'. In steps (2) and (2)', the mold formed by fitting the female mold and the male mold together is subjected to a second copolymerization reaction. As a result, a second copolymer is obtained that has a hydrophobic member sandwiched between the first contact lens-forming composition (copolymer) and the second contact lens-forming composition (copolymer) and has a hydrophobic member therein.

[0066] The female mold used in step (2) may be the same as or different from the mold used in step (1). For example, if the first copolymer is contained in the recesses of the female mold when recovered in step (1), the female mold containing the first copolymer may be used as is in step (2). Similarly, the male mold used in step (2)' may be the same as or different from the mold used in step (1)'. For example, if the first copolymer is attached to the protrusions of the male mold when recovered in step (1)', the male mold to which the first copolymer is attached may be used as is in step (2)'.

[0067] The second composition for forming a contact lens may be the same as or different from the first composition for forming a contact lens used in steps (1) and (1)'. The second copolymerization reaction may be carried out depending on the contents of the second composition for forming a contact lens, and may be carried out under the same conditions as those for the first copolymerization reaction, or under different conditions.

[0068] From the viewpoint of ease of recovery, the second copolymer obtained in step (2) is preferably attached to the top surfaces of the convex portions of the male mold after the second copolymerization reaction. The method of attaching the second copolymer to the male mold can be carried out by replacing the female mold with the male mold in the method of attaching the first copolymer to the female mold in step (1). The second copolymer obtained in step (2)' is also preferably attached to the top surfaces of the convex portions of the male mold after the second copolymerization reaction.

[0069] The method for attaching the first copolymer to the female mold in step (1) and the method for attaching the second copolymer to the male mold in step (2) can be the methods described above, but physical treatment methods such as corona discharge or plasma irradiation are preferred because they can easily modify the surface of the mold. The method for attaching the first copolymer to the male mold in step (1)' can be the methods described above, but physical treatment methods such as corona discharge or plasma irradiation are preferred because they can easily modify the surface of the mold. If the male mold is physically treated by corona discharge or plasma irradiation before step (1)', the second copolymer can, in principle, be attached to the male mold after step (2)'.

[0070] [Steps (3) and (3)' for Obtaining a Hybrid Contact Lens Encapsulating a Hydrophobic Material] In steps (3) and (3)', the second copolymer is subjected to a hydration swelling treatment to obtain a hybrid contact lens encapsulating a hydrophobic material. In steps (3) and (3)', for example, after separating the female mold from the male mold, the male mold to which the second copolymer is attached may be immersed in an aqueous solution to hydrate and swell the second copolymer. Upon hydration swelling, the second copolymer peels off from the male mold, thereby obtaining a hybrid contact lens encapsulating a hydrophobic material. The second copolymer and / or the hybrid contact lens may be subjected to processing such as cutting and polishing, if necessary.

[0071] The hydration and swelling treatment may be any hydration and swelling treatment using a swelling liquid that is employed in ordinary contact lens manufacturing methods, and examples thereof include hydration and swelling treatments using swelling liquids such as water, physiological saline, isotonic buffer solutions such as phosphate buffer solutions, organic solvents, and mixtures of water and organic solvents.

[0072] The organic solvent used as the swelling liquid is, for example, a primary or secondary alcohol, and specific examples thereof include methanol, ethanol, propanol, isopropanol, n-butanol, isobutanol, etc. As the organic solvent used in the hydration swelling treatment, one of these may be used alone, or two or more may be mixed and blended.

[0073] In the hydration swelling treatment in steps (3) and (3)', the second copolymer is preferably brought into a swollen state by, for example, immersing the male mold having the second copolymer attached thereto or the second copolymer for about 10 minutes to 1 hour in a swelling solution heated to 60° C. to 100° C. In addition, in the hydration swelling treatment, it is preferable to remove unreacted components contained in the second copolymer.

[0074] The hybrid contact lenses containing a hydrophobic material obtained in steps (3) and (3)' are preferably subjected to a sterilization treatment, such as autoclave sterilization, which is commonly employed in the production of contact lenses.

[0075] The method of one aspect of the present invention may be any method in which steps (1) to (3) are carried out or in which steps (1)' to (3)' are carried out, and may include various steps or operations between or during the steps as long as the problem of the present invention can be solved. However, it is preferable to carry out steps (1) to (3) or steps (1)' to (3)' continuously.

[0076] [Hybrid Contact Lens of One Aspect of the Present Invention] According to another aspect of the present invention, there is provided a hybrid contact lens containing a hydrophobic member obtained by the method of one aspect of the present invention.

[0077] The hybrid contact lens containing a hydrophobic member may have various properties as long as it is obtained by the method of one aspect of the present invention, but since the contained hydrophobic member is chemically bonded to the contact lens substrate, it has excellent adhesion between the hydrophobic member and the contact lens substrate, and between the contact lens substrates themselves. In connection with this excellent adhesion, the hybrid contact lens containing a hydrophobic member also has good contact lens shape and / or transparency.

[0078] The adhesion, contact lens shape, and transparency of a hybrid contact lens containing a hydrophobic material can be evaluated by the methods described in the Examples below. The contact lens containing a hydrophobic material may be evaluated as "+" for adhesion, but it is preferable that the adhesion is evaluated as "+" and the contact lens shape or transparency is evaluated as "+", and it is more preferable that all of the adhesion, contact lens shape, and transparency are evaluated as "+".

[0079] The method and application of hybrid contact lenses incorporating a hydrophobic material are not particularly limited, but they can be used as medical devices for vision correction, similar to conventional hydrogel contact lenses. Furthermore, hybrid contact lenses incorporating a hydrophobic material may have functions other than vision correction, depending on the properties of the incorporated hydrophobic material. Hybrid contact lenses incorporating a hydrophobic material preferably have improved oxygen permeability.

[0080] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples, and the present invention can take various forms as long as the object of the present invention can be achieved.

[0081] [1. Production of Hydrophobic Members] (1-1) Hydrophobic Member 1 A mixture of elastomer stock solution ("MED-6015" manufactured by NuSil Technology) consisting of two liquids with different viscosities (Part A liquid and Part B liquid) was obtained by weighing out Part A liquid and Part B liquid so that the mixing ratio was A:B = 10:1. The mixture was stirred at room temperature for 30 minutes using a magnetic stirrer. The resulting elastomer mixture was allowed to stand in a vacuum desiccator for 10 minutes to remove unnecessary gas.

[0082] The elastomer mixture was poured into the female mold of a pair of polypropylene resin molding dies, and then the male mold was fitted in. The resin mold containing the elastomer mixture was left to stand in a thermostatic chamber set at 90°C for 1 hour to cure the elastomer mixture.

[0083] After the curing treatment, the resin mold was allowed to cool to room temperature, and then the male and female molds were separated to remove the hydrophobic member 1 (silicone elastomer) from the mold. The hydrophobic member 1 had a diameter of 9.00 mm, a radius of curvature near the center of 9.00 mm, and a thickness of 0.1 mm.

[0084] (1-2) Hydrophobic Member 2 Hydrophobic member 2 was obtained in the same manner as in (1-1) above, except that "MED-6010" (manufactured by NuSil Technology) was used as the elastomer stock solution.

[0085] (1-3) Hydrophobic Material 3 30 mg of benzophenone was weighed out and placed in 4 mL of acetone in a container, and the resulting mixture was stirred at room temperature for 5 minutes to prepare a benzophenone-acetone solution.

[0086] A hydrophobic member 3 was obtained in the same manner as in (1-1) above, except that a 4% (externally added concentration) benzophenone-acetone solution was added to 0.97 mL of the elastomer stock solution "MED-6015."

[0087] (1-4) Hydrophobic Member 4 A monomer solution containing 55 wt% α,ω-di(3-methacryloyloxypropyl)polydimethylsiloxane, 15 wt% tris(trimethylsiloxy)silylpropyl methacrylate, 15 wt% octafluoropentyl methacrylate, and 15 wt% tridecyl methacrylate was added with 3,000 ppm (externally added concentration) of azobisisobutyronitrile (AIBN) based on the total amount of the monomer solution, and then stirred and mixed to obtain a monomer mixture. The mold containing the resulting monomer mixture was heated to a temperature range of 30°C to 110°C over 17 hours to undergo a copolymerization reaction. After the copolymerization reaction, the mold was allowed to cool to room temperature, and the male and female molds were separated to remove the hydrophobic member 4 (silicone-containing polymer compound) from the mold.

[0088] [2. Production of Composition for Forming Contact Lenses] (2-1) Composition 1 for Forming Contact Lenses 88 wt % of 2-hydroxyethyl methacrylate (HEMA), 7 wt % of methyl methacrylate (MMA), and 5 wt % of triethylene glycol dimethacrylate (3EG) were weighed out and stirred at room temperature for 30 minutes until the components became uniform, thereby obtaining a monomer mixture.

[0089] Next, 80 wt % of the prepared monomer mixture and 20 wt % of polyethylene glycol 600 (PEG600) were weighed into a solution to obtain, and 5,000 ppm (externally added concentration) of bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide was added relative to the total amount of the solution, followed by stirring and mixing to obtain a contact lens-forming composition 1.

[0090] (2-2) Composition 2 for forming contact lenses A solution was obtained by weighing out 90 wt % of the monomer mixture prepared in (2-1) above and 10 wt % of polyethylene glycol 600 (PEG600), and 5,000 ppm (externally added concentration) of bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide relative to the total amount of the solution was then added, followed by stirring and mixing to obtain composition 2 for forming contact lenses.

[0091] (2-3) Composition 3 for forming contact lenses To 100 wt % of the monomer mixture prepared in (2-1) above, 5,000 ppm (externally added concentration) of bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide was added to the mixture, and the mixture was stirred and mixed to obtain composition 3 for forming contact lenses.

[0092] 3. Production of Hybrid Contact Lenses (3-1) Hybrid Contact Lenses of Example 1 and Reference Example 1 An aqueous solution was prepared by weighing out 1.0 wt % of 3-methacryloxypropyltrimethoxysilane (a silane coupling agent), 1.0 wt % of acetic acid, and 0.5 wt % of a polyoxyethylene polyoxypropylene block polymer ("Lutrol F127", manufactured by BASF Japan Ltd.), which is a nonionic surfactant, and stirring was continued at room temperature for 30 minutes until the components became uniform, thereby obtaining an aqueous solution containing the silane coupling agent.

[0093] The surface of the hydrophobic member 1 was subjected to oxygen plasma treatment under conditions of a vacuum degree of 8 Pa, a current value of 20 mA, and a time period of 30 seconds. The treated hydrophobic member 1 was subjected to a silane coupling treatment by immersing it in an aqueous solution containing a silane coupling agent and leaving it in a thermostatic chamber set at 50°C for 3 hours, thereby obtaining a silane coupling-treated hydrophobic member 1.

[0094] The silane coupling-treated hydrophobic member 1 was taken out of the aqueous solution, lightly rinsed with pure water to remove excess aqueous solution, and then dried for 1 hour in a thermostatic chamber set at 90°C to obtain a hydrophobic member 1 having polymerizable functional groups introduced onto its surface.

[0095] The hydrophobic member 1 with polymerizable functional groups introduced onto its surface was held with tweezers and placed on the top surface of the convex portion of a male mold (having the same radius of curvature as the mold used to manufacture the hydrophobic member 1) in a molding die made of polypropylene resin.

[0096] The inner surface of the female mold was subjected to vacuum plasma treatment under conditions of a vacuum degree of 8 Pa, a current value of 20 mA, and a time period of 3 seconds. An appropriate amount of contact lens-forming composition 1, a raw material for a contact lens substrate, was poured into the recess of the female mold after the vacuum plasma treatment. The male mold having hydrophobic member 1 placed thereon and the female mold containing contact lens-forming composition 1 were fitted together to form an integrated mold, which was then subjected to ultraviolet irradiation treatment for 30 minutes at room temperature using an ultraviolet irradiation device, thereby carrying out a first copolymerization reaction.

[0097] The male mold was separated, and an appropriate amount of contact lens-forming composition 1 was poured into the female mold, whose recessed surface now had the first copolymer having hydrophobic material 1 extending from the surface that had been in contact with the male mold to the interior. The convex portion of the male mold was subjected to vacuum plasma treatment under conditions of a vacuum degree of 8 Pa, a current value of 20 mA, and a time period of 8 seconds. The male mold after the vacuum plasma treatment was fitted into the female mold to form an integrated mold, and the resulting mold was subjected to ultraviolet irradiation treatment for 30 minutes at room temperature using an ultraviolet irradiation device, thereby carrying out a second copolymerization reaction.

[0098] The female mold was separated, and the male mold with the second copolymer attached to the surface of the convex portions and having the hydrophobic material 1 embedded therein was brought into contact with a phosphate buffer solution at 60°C with the convex portions facing downward and left to stand for 30 minutes, causing the hydrogel in which the second copolymer had swollen to swell and peel off from the male mold. The swollen hydrogel was transferred to fresh phosphate buffer solution and subjected to autoclave sterilization at 121°C for 30 minutes, yielding the hybrid contact lens of Example 1.

[0099] The hybrid contact lens of Example 1 had a diameter of 14.36 mm, a radius of curvature near the center of 9.00 mm, and a thickness of 0.2 mm.

[0100] On the other hand, a hybrid contact lens of Reference Example 1 was obtained in the same manner as above, except that the silane coupling treatment was not carried out.

[0101] (3-2) Hybrid Contact Lenses of Examples 2 to 4 The hybrid contact lenses of Examples 2 to 4 were obtained in the same manner as in (3-1) above, except that hydrophobic members 2 to 4 were used.

[0102] (3-3) Hybrid Contact Lenses of Examples 5 and 6 Hybrid contact lenses of Examples 5 and 6 were obtained in the same manner as in (3-1) above, except that contact lens-forming compositions 2 and 3 were used.

[0103] (3-4) Hybrid Contact Lens of Example 7 The hybrid contact lens of Example 7 was obtained in the same manner as in (3-1) above, except that trimethoxy(7-octen-1-yl)silane was used as the silane coupling agent.

[0104] (3-5) Hybrid Contact Lens of Example 8 A hydrophobic member 1 having a polymerizable functional group introduced on the surface thereof was obtained in the same manner as in the method described in (3-1) above.

[0105] The hydrophobic member 1 with polymerizable functional groups introduced onto its surface was held with tweezers and placed on the bottom of the recess of a female mold (having the same radius of curvature as the mold used to manufacture the hydrophobic member 1) in a polypropylene resin molding die.

[0106] The convex surface of the male mold was subjected to vacuum plasma treatment under conditions of a vacuum degree of 8 Pa, a current value of 20 mA, and a time period of 3 seconds. An appropriate amount of contact lens-forming composition 1, a raw material for a contact lens substrate, was poured into the recess of the female mold on which hydrophobic member 1 had been placed. The male mold after the vacuum plasma treatment was fitted into the female mold containing hydrophobic member 1 and contact lens-forming composition 1 to form an integrated mold, and the mold was then subjected to ultraviolet irradiation treatment for 30 minutes at room temperature using an ultraviolet irradiation device, thereby carrying out a first copolymerization reaction.

[0107] The male mold, with the first copolymer having the hydrophobic member 1 extending from the surface that had been in contact with the female mold to the interior and adhering to the convex surfaces, was separated, and an appropriate amount of contact lens-forming composition 1 was poured into the female mold. The above male mold and female mold were fitted together to form an integrated mold, and the mold was subjected to ultraviolet irradiation treatment at room temperature for 30 minutes using an ultraviolet irradiation device, thereby carrying out a second copolymerization reaction.

[0108] The female mold was separated, and the male mold with the second copolymer attached to the surface of the convex portions and having the hydrophobic material 1 embedded therein was brought into contact with a phosphate buffer solution at 60°C with the convex portions facing downward and left to stand for 30 minutes, causing the hydrogel in which the second copolymer had swollen to swell and peel off from the male mold. The swollen hydrogel was transferred to fresh phosphate buffer solution and subjected to autoclave sterilization at 121°C for 30 minutes, yielding the hybrid contact lens of Example 8.

[0109] (3-6) Hybrid Contact Lenses of Comparative Examples 1 and 2 The hybrid contact lens of Comparative Example 1 was obtained by the same method as in (3-1) above, except that 3-aminopropyltriethoxysilane was used as the silane coupling agent. The hybrid contact lens of Comparative Example 2 was obtained by the same method as in (3-1) above, except that 3-glycidoxypropyltrimethoxysilane was used as the silane coupling agent.

[0110] 4. Evaluation Method The hybrid contact lenses of Examples 1 to 8, Comparative Examples 1 and 2, and Reference Example 1 were evaluated according to the following evaluation criteria.

[0111] (4-1) Adhesion The hybrid contact lenses of Examples 1 to 8, Comparative Examples 1 and 2, and Reference Example 1 were immersed in a 100% ethanol solution at room temperature to make them overswollen. The overswollen hybrid contact lenses were visually inspected for peeling between the hydrophobic member and the contact lens substrate, and evaluated according to the following criteria.

[0112] +: No peeling was observed -: Peeling was observed

[0113] (4-2) Contact Lens Shape Quality For the hybrid contact lenses of Examples 1 to 8, distortion of the peripheral shape was confirmed as the contact lens shape quality using a dimension analyzer (manufactured by JCF / OPTIMEC), and evaluated according to the following criteria.

[0114] +: No distortion was observed -: Distortion was observed

[0115] (4-3) Transparency The transparency of the hybrid contact lenses of Examples 1 to 8 was evaluated by the following method.

[0116] The light transmittance at the center of the hybrid contact lens was read at 10 nm intervals in the wavelength range of 380 nm to 780 nm, and the luminous transmittance τv was calculated according to the following formula 1 using a method in accordance with JIS Z 8722. The weighting coefficient was calculated using a visual field of 10° and a standard illuminant of D65.

[0117] T(λ): Solid angle transmittance S(λ): Value at wavelength λ of the D65 spectral distribution of standard light y(λ): Value of the color matching function in the X10Y10Z10 color system (relative luminosity factor) S(λ)y(λ): Weighting coefficient Δλ: Wavelength interval (10 nm)

[0118] Using the calculated luminous transmittance, transparency was evaluated according to the following criteria.

[0119] +: Visual transmittance was 90% or more. -: Visual transmittance was less than 90%.

[0120] [5. Evaluation Results] The evaluation results for adhesion, contact lens shapeability, and transparency are shown in Table 1. A photograph of a cross section of the hybrid contact lens of Example 1 cut in the diameter direction, observed and photographed with a digital microscope (20x magnification), is shown in Figure 2. A photograph of the hybrid contact lens of Example 1 observed and photographed from above in the vertical direction with a digital microscope (20x magnification) is shown in Figure 3, and a photograph of the hybrid contact lens of Reference Example 1 observed and photographed from above in the vertical direction with a digital microscope (20x magnification) is shown in Figure 4.

[0121] As shown in Table 1, the hybrid contact lenses of Examples 1 to 8 were excellent in all respects of adhesion, contact lens shape (peripheral shape), and transparency. Furthermore, as shown in Figures 2 and 3, the hybrid contact lens of Example 1 had a stable shape despite the contact lens substrate incorporating the hydrophobic member 1. Similarly to the hybrid contact lens of Example 1, the hybrid contact lenses of Examples 2 to 8 also had a stable shape despite incorporating the hydrophobic member. Furthermore, as shown in Figure 4, the hybrid contact lens of Reference Example 1, which was produced using a hydrophobic member that had not been silane coupling treated, had an overall wavy shape and was unusable as a contact lens.

[0122] In contrast, as shown in Table 1, the hybrid contact lenses of Comparative Examples 1 and 2 had poor adhesion to the contact lens substrate because one end (organic functional group) of the silane coupling agent used was an amino group or an epoxy group. Therefore, the hybrid contact lenses of Comparative Examples 1 and 2 could not be used as contact lenses.

[0123]

[0124] The method of one embodiment of the present invention allows hybrid contact lenses to be produced simply and easily without complex steps, making it suitable for industrial production of hybrid contact lenses. Furthermore, the hybrid contact lens of one embodiment of the present invention has high adhesion and can stably contain a hydrophobic material, making it suitable for everyday use as a hybrid contact lens that has the functions exhibited by a hydrophobic material, such as oxygen permeability.

[0125] 1: First male mold 2: First female mold 3: Second male mold 4: Second female mold 10: Hybrid contact lens 11: Hydrogel contact lens substrate 12: Hydrophobic member 101: First contact lens-forming composition 102: Second contact lens-forming composition 111: First contact lens layer 112: Second contact lens layer 121: First copolymer 122: Second copolymer CROSS-REFERENCE TO RELATED APPLICATIONS

[0126] This application claims priority from Japanese Patent Application No. 2023-133880, filed August 21, 2023, the entire disclosure of which is incorporated herein by reference. In addition, the entire disclosures of all documents referenced in the detailed description of the invention of this application, including Patent Documents 1 and 2, are incorporated herein by reference.

Claims

1. A method for producing a hybrid contact lens containing a hydrophobic member, comprising: a step of: subjecting a molding die, which is made up of a male die having a hydrophobic member having a polymerizable functional group on its surface placed on the top surface of a convex portion and a female die containing a first contact lens forming composition in its concave portion, to a first copolymerization reaction to obtain a first copolymer having the hydrophobic member from the surface in contact with the male die to its inside; a step of subjecting a molding die, which is made up of a female die having a second contact lens forming composition on top of the first copolymer in its concave portion, to a second copolymerization reaction to obtain a second copolymer having the hydrophobic member inside; and a step of subjecting the second copolymer to a hydration swelling treatment to obtain a hybrid contact lens containing a hydrophobic member.

2. A method for producing a hybrid contact lens containing a hydrophobic member, comprising: a step of placing a hydrophobic member having a polymerizable functional group on the surface of the bottom of a recess, and subjecting a molding die having a female die containing a first contact lens composition in the recess and a male die fitted together, to a first copolymerization reaction to obtain a first copolymer having the hydrophobic member from the surface in contact with the female die to the inside; a step of subjecting a molding die having a female die containing a second contact lens composition in the recess and a male die having the first copolymer on the top surface of the convex part fitted together, to a second copolymerization reaction to obtain a second copolymer having the hydrophobic member inside; and a step of subjecting the second copolymer to a hydration swelling treatment to obtain a hybrid contact lens containing a hydrophobic member.

3. A method for producing a hybrid contact lens according to claim 1 or 2, further comprising a step of treating the hydrophobic material with a silane coupling agent whose organic functional group is a polymerizable functional group, thereby obtaining a hydrophobic material having a polymerizable functional group on the surface.

4. The method for producing a hybrid contact lens according to claim 1 or 2, wherein the hydrophobic material is a hydrophobic material selected from the group consisting of thermoplastic elastomers, thermosetting elastomers, thermosetting polymers and thermoplastic polymers.

5. The method for manufacturing a hybrid contact lens according to claim 1 or 2, wherein the hydrophobic member is a hydrophobic member having through holes.

6. A hybrid contact lens obtained by the manufacturing method according to claim 1 or 2.

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