Patent Application
20220332875
The present disclosure relates to a contact lens and a manufacturing method thereof.
With the increasing popularity of contact lenses, the comfort, lubricity, and oxygen-permeability of the contact lenses have become more and more important to wearers. The use of higher permeability materials in the manufacture of contact lenses has become a trend, and this has motivated manufacturers to use siloxane-based materials to manufacture silicone hydrogel lenses. However, the silicone hydrogel lenses are hydrophobic, and therefore do not have good wetting properties. Therefore, manufacturers have been developing techniques to treat the lens surface, for example, by using a plasma treatment. However, the plasma treatment has the problem of high production costs.
In view of the above, there is a need to provide a new technique to treat the lens surface.
The present disclosure provides a contact lens including a lens body and a hydrophilic surface modification layer. The lens body is formed by a lens composition including a reactive additive, in which the reactive additive has a reactive functional group, and a surface of the lens body has the reactive functional group. The hydrophilic surface modification layer includes a modification layer and a first hydrophilic layer, in which the modification layer is adhered on the surface of the lens body by covalently bonding to the reactive functional group, and the first hydrophilic layer is formed on the modification layer by covalently bonding a first hydrophilic compound to the modification layer.
In some embodiments, the hydrophilic surface modification layer includes a plurality of hydrophilic resin structures dispersed on a first portion of the surface of the lens body, a second portion of the surface of the lens body is exposed, and a third portion of the modification layer is exposed.
In some embodiments, the modification layer is formed on the surface of the lens body by covalently bonding a compound containing an azetidinium group, an epoxy group, a vinyl group, or combinations thereof to the reactive functional group.
In some embodiments, the compound containing the azetidinium group includes an azetidinium-containing epichlorohydrin-functionalized polyamine, an azetidinium-containing epichlorohydrin-functionalized polyamidoamine, or combinations thereof.
In some embodiments, the reactive functional group includes a carboxyl group, an amino group, a thiol group, a hydroxyl group, or combinations thereof.
In some embodiments, the reactive additive includes acrylic acid, methacrylic acid, maleic acid, fumaric acid, aconitic acid, mesaconitic acid, citraconic acid, itaconitic acid, angelic acid, allylamine, 2-acrylamido-2-methylpropane sulfonic acid, vinylsulfonic acid, or combinations thereof.
In some embodiments, the content of the reactive additive in the lens composition is between 0.1 wt % and 10 wt %.
In some embodiments, the first hydrophilic compound includes a monosaccharide having a carboxyl group or an amino group, a disaccharide having a carboxyl group or an amino group, an oligosaccharide having a carboxyl group or an amino group, a polysaccharide having a carboxyl group or an amino group, or combinations thereof.
In some embodiments, the first hydrophilic compound includes hyaluronic acid, alginic acid, chondroitin sulfate, polyglutamic acid, sodium pyrrolidone carboxylate (sodium PCA), nicotinamide, derivatives of the above compounds, salts of the above acids, or combinations thereof.
In some embodiments, the first hydrophilic compound is a copolymer formed by copolymerizing at least one first monomer and at least one second monomer, in which the first monomer is a reactive vinylic monomer containing a carboxyl group or an amino group, and the second monomer is a non-reactive vinylic monomer.
In some embodiments, the reactive vinylic monomer includes acrylic acid, vinyl-functionalized acrylic acid, methacrylic acid, maleic acid, fumaric acid, aconitic acid, mesaconitic acid, citraconic acid, itaconitic acid, angelic acid, allylamine, 2-acrylamido-2-methylpropane sulfonic acid, vinylsulfonic acid, or combinations thereof.
In some embodiments, the non-reactive vinylic monomer includes acrylamide, phosphocholine, polyethylene glycol, 2-aminoethyl methacrylate hydrochloride, N-vinylpyrrolidone, N,N-dimethacrylamide, or combinations thereof.
In some embodiments, the non-reactive vinylic monomer is 55 wt % or more in the at least one first monomer and the at least one second monomer.
In some embodiments, the hydrophilic surface modification layer further includes a second hydrophilic layer formed on the first hydrophilic layer by covalently bonding a second hydrophilic compound to the first hydrophilic layer.
In some embodiments, the hydrophilic surface modification layer has a thickness of less than or equal to 100 nm.
In some embodiments, the contact lens of any one of the above embodiments has a contact angle hysteresis of less than or equal to 30 degrees.
The present disclosure provides a manufacturing method of a contact lens including the following operations. (i) A curing reaction is performed on a lens composition to form a lens body, in which the lens composition includes a reactive additive, the reactive additive has a reactive functional group, and a surface of the lens body has the reactive functional group. (ii) A surface modification is performed on the lens body. The surface modification includes forming a modification layer on the lens body, in which the modification layer is adhered on the surface of the lens body by covalently bonding to the reactive functional group; and contacting the lens body having the modification layer with a first hydrophilic compound, in which the first hydrophilic compound reacts with the modification layer to form a covalent bond, thereby forming a first hydrophilic layer on the modification layer.
In some embodiments, performing the surface modification on the lens body is performed in a process of extraction and wetting.
In some embodiments, forming the modification layer on the lens body includes: contacting the lens body with a compound containing an azetidinium group, an epoxy group, a vinyl group, or combinations thereof, in which the compound reacts with the reactive functional group to form a covalent bond, thereby forming the modification layer.
In some embodiments, a first reaction time of the compound reacting with the reactive functional group is between 10 minutes and 12 hours, and a second reaction time of the first hydrophilic compound reacting with the modification layer is between 10 minutes and 12 hours.
In some embodiments, contacting the lens body with the compound containing the azetidinium group, the epoxy group, the vinyl group, or combinations thereof is performed at a first reaction temperature of between 20° C. and 140° C.
In some embodiments, the first reaction temperature is between 20° C. and 40° C.
In some embodiments, the compound containing the azetidinium group includes an azetidinium-containing epichlorohydrin-functionalized polyamine, an azetidinium-containing epichlorohydrin-functionalized polyamidoamine, or combinations thereof.
In some embodiments, the lens body is not treated by a plasma treatment before performing the surface modification on the lens body.
In some embodiments, the reactive functional group includes a carboxyl group, an amino group, a thiol group, a hydroxyl group, or combinations thereof.
In some embodiments, the reactive additive includes acrylic acid, methacrylic acid, maleic acid, fumaric acid, aconitic acid, mesaconitic acid, citraconic acid, itaconitic acid, angelic acid, allylamine, 2-acrylamido-2-methylpropane sulfonic acid, vinylsulfonic acid, or combinations thereof.
In some embodiments, the content of the reactive additive in the lens composition is between 0.1 wt % and 10 wt %.
In some embodiments, the first hydrophilic compound includes a monosaccharide having a carboxyl group or an amino group, a disaccharide having a carboxyl group or an amino group, an oligosaccharide having a carboxyl group or an amino group, a polysaccharide having a carboxyl group or an amino group, or combinations thereof.
In some embodiments, the first hydrophilic compound is a copolymer formed by copolymerizing at least one first monomer and at least one second monomer, the first monomer is a reactive vinylic monomer containing a carboxyl group or an amino group, and the second monomer is a non-reactive vinylic monomer.
In some embodiments, the reactive vinylic monomer includes acrylic acid, vinyl-functionalized acrylic acid, methacrylic acid, maleic acid, fumaric acid, aconitic acid, mesaconitic acid, citraconic acid, itaconitic acid, angelic acid, allylamine, 2-acrylamido-2-methylpropane sulfonic acid, vinylsulfonic acid, or combinations thereof.
In some embodiments, the non-reactive vinylic monomer includes acrylamide, phosphocholine, polyethylene glycol, 2-aminoethyl methacrylate hydrochloride, N-vinylpyrrolidone, N,N-dimethacrylamide, or combinations thereof.
In some embodiments, the manufacturing method of the contact lens further includes contacting the lens body having the modification layer and the first hydrophilic layer with a second hydrophilic compound, in which the second hydrophilic compound reacts with the first hydrophilic layer to form a covalent bond, thereby forming a second hydrophilic layer on the first hydrophilic layer.
It is to be understood that both the foregoing general description and the following detailed description are by examples, and are intended to provide further explanation of the invention as claimed.
The disclosure can be more fully understood by reading the following detailed description of the embodiment, with reference made to the accompanying drawings as follows:
The following embodiments are disclosed with accompanying diagrams for detailed description. For illustration clarity, many details of practice are explained in the following descriptions. However, it should be understood that these details of practice do not intend to limit the present disclosure. That is, these details of practice are not necessary in parts of embodiments of the present disclosure. Furthermore, for simplifying the drawings, some of the conventional structures and elements are shown with schematic illustrations.
In the present specification, a range represented by “a numerical value to another numerical value” is a schematic representation for avoiding listing all of the numerical values in the range in the specification. Therefore, the recitation of a specific numerical range covers any numerical value in the numerical range and a smaller numerical range defined by any numerical value in the numerical range, as is the case with the any numerical value and the smaller numerical range stated explicitly in the specification.
Although a series of operations or steps are used below to describe the method disclosed herein, an order of these operations or steps should not be construed as a limitation to the present disclosure. For example, some operations or steps may be performed in a different order and/or other steps may be performed at the same time. In addition, all shown operations, steps and/or features are not required to be executed to implement an embodiment of the present disclosure. In addition, each operation or step described herein may include a plurality of sub-steps or actions.
The present disclosure provides a contact lens including a lens body and a hydrophilic surface modification layer. The lens body is formed by a lens composition including a reactive additive, in which the reactive additive has a reactive functional group, and a surface of the lens body has the reactive functional group. In some embodiments, the reactive functional group includes a carboxyl group, an amino group, a thiol group, a hydroxyl group, or combinations thereof. The hydrophilic surface modification layer includes a modification layer and a first hydrophilic layer. The modification layer is adhered on the surface of the lens body by covalently bonding to the reactive functional group. The first hydrophilic layer is formed on the modification layer by covalently bonding a first hydrophilic compound to the modification layer. In some embodiments, the modification layer is formed on the surface of the lens body by covalently bonding a compound containing an azetidinium group, an epoxy group, a vinyl group, or combinations thereof to the reactive functional group. In some embodiments, the hydrophilic surface modification layer includes modification layers and first hydrophilic layers, and the surface of the lens body is covered by the modification layer, the first hydrophilic layer, the modification layer, the first hydrophilic layer, etc., sequentially. The number of the modification layers and the first hydrophilic layers can be adjusted according to the design requirements. In some embodiments, the hydrophilic surface modification layer has a thickness of less than or equal to 100 nm, such as 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 70, 80, 90, or 100 nm. The azetidinium group is a positively charged group and has a structure as shown in the following formula (1):
In the present disclosure, the lens body is formed by the lens composition including the reactive additive, so that the surface of the lens body has the reactive functional group that can be covalently bonded to the compound containing the azetidinium group, the epoxy group, the vinyl group, or combinations thereof. Compared with a process of forming a lens body and then treating the lens body with plasma, the present disclosure simplifies the process of manufacturing the contact lens, reduces the complexity of the process, and reduces the manufacturing cost.
In some embodiments, the hydrophilic surface modification layer includes a plurality of hydrophilic resin structures dispersed on a first portion of the surface of the lens body, a second portion of the surface of the lens body is exposed, and a third portion of the modification layer is exposed. Further explanations will be provided with phase images taken with an AFM.
In some embodiments, the contact lens has a contact angle hysteresis of less than or equal to 30 degrees. For example, the contact angle hysteresis is in the range of 1 degree to 30 degrees, such as 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 25, or 30 degrees. It can be seen that the contact lens of the present disclosure has excellent hydrophilicity.
In some embodiments, the hydrophilic surface modification layer further includes a second hydrophilic layer formed on the first hydrophilic layer by covalently bonding a second hydrophilic compound to the first hydrophilic layer. The type of second hydrophilic compound can be selected according to the manufacturer design requirements to give the contact lens the desired properties.
The present disclosure provides a manufacturing method of a contact lens including the following operations. (i) A curing reaction is performed on a lens composition to form a lens body, in which the lens composition includes a reactive additive, the reactive additive has a reactive functional group, and a surface of the lens body has the reactive functional group. In some embodiments, the reactive functional group includes a carboxyl group, an amino group, a thiol group, a hydroxyl group, or combinations thereof. (ii) A surface modification is performed on the lens body. The surface modification includes forming a modification layer on the lens body, in which the modification layer is adhered on the surface of the lens body by covalently bonding to the reactive functional group; and contacting the lens body having the modification layer with a first hydrophilic compound, in which the first hydrophilic compound reacts with the modification layer to form a covalent bond, thereby forming a first hydrophilic layer on the modification layer.
In some embodiments, forming the modification layer on the lens body includes: contacting the lens body with a compound containing an azetidinium group, an epoxy group, a vinyl group, or combinations thereof. The compound reacts with the reactive functional group to form a covalent bond, thereby forming the modification layer. In the operation of performing the surface modification on the lens body, only a low-temperature environment is required to react the compound containing the azetidinium group, the epoxy group, the vinyl group, or combinations thereof with the reactive functional group to form sufficient covalent bonds. Therefore, the modification layer with good adhesion is formed on the surface of the lens body. The manufacturing method of the present disclosure is capable of producing the contact lens with excellent hydrophilicity at low temperature. In some embodiments, contacting the lens body with the compound containing the azetidinium group, the epoxy group, the vinyl group, or combinations thereof is performed at a first reaction temperature of between 20° C. and 140° C. In some embodiments, the first reaction temperature is between 20° C. and 40° C.
From the above steps, it can be known that the modification layer and the first hydrophilic layer are formed in two different steps. It can be seen that the modification layer is interposed between the lens body and the first hydrophilic layer. In some embodiments, the compound and the first hydrophilic compound form a cross-linked structure that covers the surface of the lens body.
In some embodiments, performing the surface modification on the lens body is performed in a process of extraction and wetting. In other words, the surface modification operation of the present disclosure can be integrated in the extraction and wetting process of the existing contact lens preparation. Therefore, the surface modification of the lens body can be performed without significant adjustment of the existing process and equipment.
In some embodiments, the manufacturing method of the contact lens further includes contacting the lens body having the modification layer and the first hydrophilic layer with a second hydrophilic compound, in which the second hydrophilic compound reacts with the first hydrophilic layer to form a covalent bond, thereby forming a second hydrophilic layer on the first hydrophilic layer. The type of second hydrophilic compound can be selected according to the manufacturer design requirements to give the contact lens the desired properties.
In some embodiments, a first reaction time of the compound reacting with the reactive functional group is between 10 minutes and 12 hours, and a second reaction time of the first hydrophilic compound reacting with the modification layer is between 10 minutes and 12 hours.
In some embodiments, the lens body is not treated by a plasma treatment before performing the surface modification on the lens body. In some embodiments, a polyionic material is not deposited on the surface of the lens body before performing the surface modification on the lens body. Therefore, compared with a process of forming the lens body and then treating the lens body with plasma, the manufacturing method of the present disclosure is more simplified, and the complexity of the process can be reduced.
In some embodiments, the operation of contacting the lens body with the compound containing the azetidinium group, the epoxy group, the vinyl group, or combinations thereof includes soaking the lens body in a solution containing the compound, in which the content of the compound is 0.005 wt % to 5 wt %, such as 0.005, 0.01, 0.02, 0.03, 0.04 0.05, 0.1, 0.5, 1, 2, 3, 4, or 5 wt %.
In some embodiments, the operation of contacting the lens body having the modification layer with the first hydrophilic compound includes: soaking the lens body having the modification layer in a solution containing the first hydrophilic compound, in which the content of the first hydrophilic compound is 0.005 wt % to 2.5 wt %, such as 0.005, 0.01, 0.05, 0.1, 0.5, 1, 1.5, 2, or 2.5 wt %.
In some embodiments, the manufacturing method of the contact lens further includes sterilizing the lens body having the modification layer and the first hydrophilic layer by an autoclaving. The autoclaving can further enhance the hydrophilicity of the contact lens and reduce the contact angle hysteresis of the contact lens.
Next, with respect to the aforementioned contact lenses and the method of manufacturing the contact lenses, the materials and content of the lens composition, the reactive additive, the first hydrophilic compound, the second hydrophilic compound, and the compound containing the azetidinium group, the epoxy group, the vinyl group, or combinations thereof are further illustrated in various embodiments.
In some embodiments, the lens composition includes a silicon polymer having a structure as shown in the following formula (2):
in which X is a secondary amine group (—NH—) or oxygen, Y is a secondary amine group (—NH—) or oxygen, at least one of X and Y is the secondary amine group (—NH—). R1 is hydrogen or methyl, R2 is a C1-C10 alkyl group, m is an integer of 2 to 4, n is an integer of 2 to 4, p is an integer of 0 to 4, q is an integer of 2 to 4, and k is an integer that makes the average molecular weight of the silicone polymer in the range of 600-3000. In some embodiments, an atomic number ratio of silicon to nitrogen is from 20:1 to 5:1. In some embodiments, the content of the silicon polymer is from 5 wt % to 50 wt % based on 100 wt % of the lens composition.
In some embodiments, when X of formula (2) is the secondary amine group (—NH—), Y is oxygen, m is 2, n is 2, p is 1, and q is 3, the silicone polymer has a structure as shown in the following formula (3):
in which k is an integer that makes the average molecular weight of the silicone polymer in the range of 600-3000, p is an integer from 0 to 4, and R2 is a C1-C10 alkyl group.
In some other embodiments, the lens composition includes a silicon polymer having a structure as shown in the following formula (4):
in which Z is O or NH; L is (CH2)e, (CH2)e—[O(CH2)a]b, or (CH2)e(CHOH)—[O(CH2)a]b; R3 is an alkyl group; R4 is OH, CH3, or OSi(CH3)3; R5 is CH3 or OSi(CH3)3; f is an integer from 1 to 30; e and a are integers from 2 to 5; and b is an integer from 1 to 5.
In some other embodiments, the lens composition includes a silicone polymer, and the silicone polymer is α-acrylamidopropyl-ω-butyl polydimethylsiloxane. However, the present disclosure is not intended to be limited in scope to the silicone polymers listed above for illustrative purposes.
In some embodiments, the lens composition further includes a hydrophilic monomer, a crosslinker, or a combination thereof. In some embodiments, the hydrophilic monomer includes N-vinylpyrrolidone (NVP), 2-hydroxyethyl methacrylate (HEMA), glycerol methacrylate (GMA), 2-hydroxy-butyl methacrylate, acrylic acid, methacrylic acid (MAA), N,N-dimethylacrylamide (DMA), N,N-dimethyl methacrylamide, N-vinyl-N-methyl acetamide, 2-methacryloyloxyethyl phosphorylcholine, or combinations thereof. In some embodiments, the crosslinker includes 1,3,5-triallyl isocyanurate (TAIC), ethylene diacrylate, ethylene glycol di(meth)acrylate (EGDA), triethylene glycol di(meth)acrylate, tetramethylene glycol di(meth)acrylae, trimethylolpropane tri(meth)acrylate (TRIM), pentaerythritol tetra(meth)acrylate, bisphenol A di(meth)acrylate, methylenebis(meth)acrylamide, divinyl ether, divinyl sulfone, divinyl benzene, trivinyl benzene, triallyl isocyanurate, triallyl phthalate, diallyl phthalate, allyl methacrylate, or combinations thereof.
In some embodiments, the reactive additive includes acrylic acid, methacrylic acid, maleic acid, fumaric acid, aconitic acid, mesaconitic acid, citraconic acid, itaconitic acid, angelic acid, allylamine, 2-acrylamido-2-methylpropane sulfonic acid, vinylsulfonic acid, or combinations thereof. In some embodiments, the content of the reactive additive in the lens composition is between 0.1 wt % and 10 wt %, such as 0.1, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 wt %. When the content of the reactive additive falls within the above-mentioned range, the lens body formed from the lens composition has sufficient reactive functional groups to react with the compounds containing the azetidinium group, the epoxy group, the vinyl group, or combinations thereof, so that the modification layer formed from the compounds has good adhesion.
In some embodiments, the first hydrophilic compound includes a monosaccharide having a carboxyl group or an amino group, a disaccharide having a carboxyl group or an amino group, an oligosaccharide having a carboxyl group or an amino group, a polysaccharide having a carboxyl group or an amino group, or combinations thereof. In some embodiments, the first hydrophilic compound includes hyaluronic acid, alginic acid, chondroitin sulfate, polyglutamic acid, sodium pyrrolidone carboxylate, nicotinamide, derivatives of the above compounds, salts of the above acids, or combinations thereof. For example, the salt of the above acids is hyaluronate, alginate, or polyglutamate. The alginate is, for example, sodium alginate.
In some embodiments, the first hydrophilic compound is a copolymer formed by copolymerizing at least one first monomer and at least one second monomer, in which the first monomer is a reactive vinylic monomer containing a carboxyl group or an amino group, and the second monomer is a non-reactive vinylic monomer. For example, the first hydrophilic compound is a copolymer formed by copolymerizing a reactive vinylic monomer and two different non-reactive vinylic monomers.
In some embodiments, the reactive vinylic monomer includes acrylic acid, vinyl-functionalized acrylic acid, methacrylic acid, maleic acid, fumaric acid, aconitic acid, mesaconitic acid, citraconic acid, itaconitic acid, angelic acid, allylamine, 2-acrylamido-2-methylpropane sulfonic acid, vinylsulfonic acid, or combinations thereof. In some embodiments, the vinyl-functionalized acrylic acid may be obtained by reacting a vinyl-functionalized reagent with acrylic acid, and the vinyl-functionalized reagent may include α-cyanoacrylate, diethylene glycol diacrylate, divinyl sulfone, or any other vinyl-functionalized reagent known in the art.
In some embodiments, the non-reactive vinylic monomer includes acrylamide, phosphocholine, polyethylene glycol, 2-aminoethyl methacrylate hydrochloride, N-vinylpyrrolidone, N,N-dimethacrylamide, or combinations thereof. The phosphocholine is, for example, 2-methacryloyloxy ethyl phosphorylcholine.
In some embodiments, the non-reactive vinylic monomer is 55 wt % or more in the at least one first monomer and the at least one second monomer. In some embodiments, the reactive vinylic monomer is 55wt % to 90wt %, for example, 55, 60, 65, 70, 75, 80, 85, or 90wt %. The content of non-reactive vinylic monomer can be adjusted according to the manufacturer design requirements to obtain the contact lens with the desired properties.
In some embodiments, the first hydrophilic compound includes a copolymer of acrylamide and vinyl-functionalized acrylic acid, or a copolymer of acrylamide, methacrylic acid, and 2-methacryloyloxy ethyl phosphorylcholine.
In some embodiments, the second hydrophilic compound is a copolymer formed by copolymerizing at least one non-reactive vinylic monomer. In some embodiments, the non-reactive vinylic monomer includes acrylamide, phosphocholine, polyethylene glycol, 2-aminoethyl methacrylate hydrochloride, N-vinylpyrrolidone, N,N-dimethacrylamide, or combinations thereof. The phosphocholine is, for example, 2-methacryloyloxy ethyl phosphorylcholine. For example, the second hydrophilic compound is a copolymer of acrylamide and 2-aminoethyl methacrylate hydrochloride. However, the present disclosure is not limited to the above compounds. The first hydrophilic compound can be modified by molecular design to have a first functional group, and the second hydrophilic compound can be modified by molecular design to have a second functional group. The first functional group and the second functional group can react to produce covalent bonding. The type of the second hydrophilic compound can be selected according to the manufacturer design requirements to give the contact lens the desired properties.
In some embodiments, the compound containing the azetidinium group includes an azetidinium-containing epichlorohydrin-functionalized polyamine, an azetidinium-containing epichlorohydrin-functionalized polyamidoamine, or combinations thereof. For example, the epichlorohydrin-functionalized polyamine is polyamide epichlorohydrin (PAE). The polyamide epichlorohydrin is also known by other names, such as polyaminoamide-epichlorohydrin, polyimide-polyamine-epichlorohydrin, polyamide-epichlorohydrin, or polyamide polyamine epichlorohydrin.
The following describes the features of the present disclosure more specifically with reference to Examples 1 to 12. Although the following embodiments are described, the materials, their amounts and ratios, processing details, processing procedures, etc., may be appropriately varied without exceeding the scope of the present disclosure. Accordingly, this disclosure should not be interpreted restrictively by the embodiments described below.
Example 1 includes the following operations. (i) N-vinylpyrrolidone (NVP), 2-hydroxyethyl methacrylate (HEMA), N,N-dimethylacrylamide (DMA), methacrylic acid (MAA), (3-methacryloxy-2-hydroxypropoxy) propyl bis(trimethyl-siloxy) methylsilane, a silicone polymer having an average molecular weight of 1500 (refer to the previous formula (3)), ethylene glycol di(meth)acrylate, 1,3,5-triallyl isocyanurate (TAIC), 2(2-hydroxy-5-methacryloxyethylphenyl)-2H-benzotriazole, a photoinitiator Irgacure 819, a reactive blue 19, and tert-amyl alcohol were mixed to form a silicone hydrogel composition. (ii) The silicone hydrogel composition was filled into a cavity of a polypropylene mold and cured under UV light for 12 min to form a lens body. (iii) After the lens body was dried and removed, the lens body was extracted in isopropanol at 40° C. for 1 hour, extracted in 50/50 (v/v) isopropanol/water at 40° C. for 1 hour, added to deionized water, and stirred at 40° C. for 1 hour. Finally, the lens body was placed in a borate buffered saline at pH 7.3-7.4 for sterilization by autoclaving to obtain a contact lens, i.e., a silicone hydrogel lens body with high oxygen-permeability.
Example 2 includes the following operations. (i) The silicone hydrogel lens body with high oxygen-permeability of Example 1 was placed in a 0.2% azetidinium-containing polyamide epichlorohydrin (PAE) solution and heated at 35° C. for 30 minutes. Afterwards, the lens body was placed in a 0.01% solution including a copolymer of acrylamide and vinyl-functionalized acrylic acid and reacted for half an hour, and then the lens body was placed in a 0.02% solution including a copolymer of acrylamide and 2-aminoethyl methacrylate hydrochloride and reacted for half an hour. (ii) The lens body was rinsed with deionized water and placed in a borate buffered saline at pH 7.4 for sterilization by autoclaving to obtain a contact lens with a surface having excellent hydrophilicity.
The surface phase image of the silicone hydrogel lens body is taken with an atomic force microscope (AFM). The AFM is operated in the tapping mode. Please refer to
As shown in
Please refer to
Several silicone hydrogel lens bodies of Example 1 and several silicone hydrogel contact lenses of Example 2 were taken for testing their dynamic contact angles (DCA). Please refer to
After several silicone hydrogel lens bodies of Example 1 and several silicone hydrogel contact lenses of Example 2 were dyed by Sudan Black dye, these lenses were taken for testing their transmittance and calculating the average transmittance. Please refer to
After several silicone hydrogel contact lenses of Example 2 were placed in an aqueous solution of isopropanol (IPA) for 3 hours, the silicone hydrogel contact lenses expanded by 30%, and the substances that were poorly cross-linked with the lens bodies fell into the solution. Afterwards, the silicone hydrogel contact lenses were washed in water and transferred to a borate buffered saline to measure their dynamic contact angles again. The average contact angle hysteresis of their surfaces was less than 5°. Please refer to
Several silicone hydrogel contact lenses of Example 2 were rubbed 300 times with finger pulps, and then their dynamic contact angles were measured. The average contact angle hysteresis of their surfaces was less than 5°. Please refer to
Example 7 includes the following operations. (i) α-acrylamidopropyl-ω-butyl polydimethylsiloxane, N,N-dimethylacrylamide (DMA), 2-hydroxyethylacrylamide (HEAA), N-vinylpyrrolidone (NVP), ethylene diacrylate, acrylic acid, 1,3,5-triallyl isocyanurate (TAIC), a photoinitiator diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TPO), a blue colorant (RB-19), and tert-amyl alcohol were mixed to form a silicone hydrogel composition. (ii) The silicone hydrogel composition was filled into a cavity of a polypropylene mold, and a light-curing reaction was carried out using a lens fabrication equipment. The lens body was formed by applying 30 mJ/cm2 of UV light for 4 minutes, 225 mJ/cm2 of UV light for 4 minutes, 300 mJ/cm2 of UV light for 2 minutes, and 470 mJ/cm2 of UV light for 2 minutes with the lens fabrication equipment. (iii) After the lens body was extracted with water, the lens body was soaked in a borate buffered saline or phosphate buffer saline of pH 7.3-7.4 and sterilized at 121° C. by autoclaving for 30 minutes to form a contact lens.
Example 8 includes the following operations. (i) The silicone hydrogel lens body of Example 7 with moderate oxygen-permeability was placed in a 0.2% azetidinium-containing polyamide epichlorohydrin (PAE) solution and heated at 31° C. for 2 hours. The lens body was placed in a 0.05% sodium alginate solution and heated at 30° C. for 1 hour. A contact lens of Example 8-1 was obtained and stored in a borate buffered saline of pH 7.4. (ii) The lens body was rinsed with deionized water and placed in a borate buffered saline at pH 7.4 for sterilization by autoclaving to obtain a contact lens of Example 8-2 having excellent hydrophilicity.
Example 9 includes the following operations. (i) The silicone hydrogel lens body with moderate oxygen-permeability of Example 7 was placed in a 0.2% azetidinium-containing polyamide epichlorohydrin (PAE) solution and heated at 31° C. for 2 hours. The lens body was placed in a 0.04% solution including a copolymer of acrylamide, methacrylic acid, and 2-methacryloyloxyethyl phosphorylcholine and heated at 30° C. for 1 hour to obtain a contact lens of Example 9-1, which was stored in a borate buffered saline at pH 7.4. (ii) The contact lens was rinsed with deionized water and placed in a borate buffered saline at pH 7.4 for sterilization by autoclaving to obtain a contact lens of Example 9-2 having excellent hydrophilicity.
Several silicone hydrogel contact lenses of Example 7, Example 8-1, and Example 8-2 were taken for testing their dynamic contact angles. Please refer to
The preparation processes of the silicone hydrogel contact lenses of Example 8-1 and Example 8-2 were repeated, and the effective contact between the lens bodies and the treatment solution (i.e., sodium alginate solution) was further improved. In detail, the treatment solution was hold in a container with mesh like holes, so that the lens bodies could uniformly contact the treatment solution during the heating process to produce the contact lenses of Example 8-1-1 and Example 8-2-1. Several silicone hydrogel contact lenses of Example 8-1-1 and Example 8-2-1 were taken for testing their dynamic contact angles. Please refer to
After several silicone hydrogel contact lenses of Example 7, Example 8-1, and Example 8-2 were dyed by Sudan Black dye, these lenses were taken for testing their transmittance and calculating the average transmittance. Please refer to
Please refer to
From the above experiment, it can be seen that the surface treatment at low temperature can effectively improve the hydrophilicity of the contact lenses, and it can be known that the autoclaving can further enhance the hydrophilicity of the contact lenses.
Several silicone hydrogel contact lenses of Example 7 and Example 9-1 were taken for testing their dynamic contact angles. Please refer to
Several silicone hydrogel contact lenses of Example 8-2 were rubbed 300 times with finger pulps, and then their dynamic contact angles were measured. The average contact angle hysteresis of their surfaces was less than 5°. Please refer to
The indentation experiment was conducted on the surfaces of contact lenses using an AFM in aqueous phase to obtain experimental data of the indentation depth and the force on the cantilever of the probe. Please refer to
In
In summary, the present disclosure provides a contact lens and a method for manufacturing a contact lens. As can be seen from the above examples, the contact lenses of the present disclosure have excellent hydrophilicity and durability. In the manufacturing method, the surface modification of the lens body requires only a low-temperature environment, and the compound containing the azetidinium group, the epoxy group, the vinyl group, or combinations thereof can react with the reactive functional group on the surface of the lens body to form the modification layer with good adhesion on the lens body. Moreover, the manufacturing method is simplified by forming the lens body by the lens composition including the reactive additive, thus reducing the complexity of the manufacturing process. The components in the solution used to soak the lens body (e.g., the solution including azetidinium-containing compounds or hydrophilic compounds) are slowly consumed and can be reused, thereby reducing the manufacturing costs.
Although the present disclosure has been described in considerable detail with reference to certain embodiments thereof, other embodiments are possible. Therefore, the spirit and scope of the appended claims should not be limited to the description of the embodiments contained herein.
It will be apparent to those skilled in the art that various modifications and variations can be made to the structure of the present disclosure without departing from the scope or spirit of the disclosure. In view of the foregoing, it is intended that the present disclosure cover modifications and variations of this disclosure provided they fall within the scope of the following claims.
| Number | Date | Country | Kind |
|---|---|---|---|
| 111109096 | Mar 2022 | TW | national |
This application claims priority to U.S. Provisional Application Ser. No. 63/175,567, filed Apr. 16, 2021, and Taiwan Application Serial Number 111109096, filed Mar. 11, 2022, the disclosures of which are incorporated herein by reference in their entireties.
| Number | Date | Country | |
|---|---|---|---|
| 63175567 | Apr 2021 | US |
