Photocuring contact lens containing microcapsules and preparation method thereof

Abstract

The invention provides a microcapsule-containing photocuring contact lens and a preparation method thereof, and relates to the field of preparation of contact lenses. The preparation method of the microcapsule-containing photocuring contact lens comprises the following steps: mixing carnosol, calendula saponin, sodium hyaluronate, ethanol and water to obtain a core material mixed solution, mixing the core material mixed solution with a polymethyl methacrylate solution under a stirring condition, and carrying out ultrasonic treatment to form an emulsion, carrying out spray drying on the emulsion to obtain microcapsules; the preparation method comprises the following steps: mixing an organic silicon monomer, an acrylate monomer, a photoinitiator, a cross-linking agent, a solvent and the microcapsule, and sequentially carrying out mold injection molding, photocuring, soaking and sterilization to obtain the microcapsule-containing photocuring contact lens. The outer-layer wall material of the microcapsule is polymethyl methacrylate, the light transmittance can reach 92%, and the refractive index of the outer-layer wall material is similar to that of a contact lens base material; carnosol and calendula officinalis glycoside in the inner layer core liquid have sterilization and fragrance effects, and sodium hyaluronate has an excellent moisturizing effect.

Description

Technical Field

[0001] The present invention relates to the technical field of contact lenses, and particularly to a photocurable contact lens containing microcapsules and a preparation method thereof. Background Art

[0002] With the increasing myopia rate among the young population, the demand for colored contact lenses and functional lenses is also getting higher and higher. Contact lens manufacturers have also started to develop and research new functional contact lenses according to the needs of consumers for contact lenses. For example, Patent CN114545658B protects a preparation method of a drug-sustained release interpenetrating network hydrogel contact lens, Patent CN115322286A discloses a contact lens for myopia prevention and control that loads and slowly releases atropine and a preparation method thereof, and Patent CN117099025A discloses a contact lens that releases WS12. Based on the above patents, it can be seen that contact lenses containing functional substances and capable of slowly releasing these functional substances are the future development direction.

[0003] The microcapsule sustained-release technology is a technology that realizes controlled release by encapsulating active substances (such as drugs, fragrances, antibacterial agents, etc.) in micron- or nanoscale wall materials, and its application in the fields of medicine, daily chemicals, food, etc. is becoming increasingly widespread. This technology provides a basis for the research of functional contact lens sheets. The existing materials for preparing the outer wall materials of microcapsules include several categories such as natural polymer materials, synthetic polymer materials, inorganic materials, organic-inorganic composite materials, and bio-based composite materials. And how to apply microcapsules to the preparation of functional contact lenses is a problem to be solved by those skilled in the art. This is because when using the microcapsule sustained-release technology to prepare contact lenses, it is necessary to consider the transparency of the outer wall material, the compatibility with the contact lens matrix material, the biological toxicity, and whether it will affect the comfort level of the contact lens.

[0004] [[ID=**14**]]In addition, after the contact lenses are prepared, they need to be sterilized comprehensively and stored in a special nursing solution in a sealed manner. However, the microcapsules have a small particle size and the outer wall material is relatively fragile. When using the existing disinfection means to disinfect the contact lenses containing microcapsules, it is easy to damage the internal microcapsules, and it may also cause the rapid dissipation of the functional substances encapsulated inside the microcapsules. For example, the temperature of high-temperature steam sterilization is 100~121°C, which is easy to cause thermal decomposition of the microcapsule wall material; ethylene oxide sterilization will affect the surface stability of the microcapsule wall material; hydrogen peroxide low-temperature plasma sterilization will damage the unsaturated double bond structure in the photocurable material; irradiation sterilization will cause crosslinking or degradation of the photocurable material, resulting in a decrease in oxygen permeability. Therefore, those skilled in the art also need to develop a sterilization method that will not damage the internal microcapsules of the contact lenses to provide technical support for the development of microcapsules in functional contact lenses. Summary of the Invention

[0005] The object of the present invention is to provide a photocurable contact lens containing microcapsules and a preparation method thereof, so as to solve the problems faced in the research and development of existing functional contact lenses, including poor compatibility between the microcapsules encapsulating functional compounds and the contact lens matrix material, resulting in a decrease in the transparency of the contact lens, and the destruction of the outer wall material of the microcapsules caused by the sterilization method.

[0006] In order to achieve the above object of the invention, the present invention provides the following technical solutions: The present invention provides a preparation method of a photocurable contact lens containing microcapsules, comprising the following steps: 1) Mix salvianol, calenduloside saponin, sodium hyaluronate, ethanol and water to obtain a core material mixture solution. Under stirring conditions, mix the core material mixture solution with a polymethyl methacrylate solution and perform ultrasonic treatment to form an emulsion. Spray-dry the emulsion to obtain microcapsules; 2) Mix organosilicon monomers, acrylate monomers, photoinitiators, crosslinkers, solvents and the microcapsules prepared in step 1), and then successively perform mold injection, photocuring, soaking and sterilization to obtain a photocurable contact lens containing microcapsules.

[0007] Preferably, in step 1), the concentration of salvianol in the core material mixture solution is 0.5 - 1.0 wt%, the concentration of calenduloside saponin is 0.2 - 1.2 wt%, and the concentration of sodium hyaluronate is 0.8 - 1.5 wt%; The volume ratio of ethanol to water is 1 - 3:97 - 99.

[0008] Preferably, in step 1), the concentration of the polymethyl methacrylate solution is 3 - 6 wt%, and the solvent is acetone.

[0009] Preferably, in step 1), the volume ratio of the core material mixture solution to the polymethyl methacrylate solution is 1:1 - 1.2; The frequency of the ultrasonic treatment is 20 - 30 kHz, and the time of the ultrasonic treatment is 5 - 15 min; The temperature of the spray drying is 70 - 120 °C.

[0010] Preferably, in step 1), the particle size of the microcapsules is 50 - 150 nm.

[0011] Preferably, in step 2), the organosilicon monomers include one or more of 3-methacryloxypropyl-tris-(trimethylsiloxy)silane, methacryloxymethyltriethoxysilane, γ-(methacryloxy)propyltrimethoxysilane, 2-methacrylic acid (pentamethyldisiloxanyl) methyl ester and 3-(trimethoxysilyl)propyl methacrylate; The acrylate monomer includes one or more of 2-hydroxyethyl methacrylate, methyl methacrylate, ethyl acrylate, and glycidyl methacrylate; The photoinitiator includes one or more of 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone, and phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide; The crosslinking agent includes one or more of ethylene glycol dimethacrylate, trimethylolpropane trimethacrylate, and 2-methacryloyloxyethyl phosphorylcholine; The solvent includes one or more of N,N-dimethylformamide, acetone, isopropyl alcohol, and ethylene glycol.

[0012] Preferably, the mixing ratio of the organosilicon monomer, acrylate monomer, photoinitiator, crosslinking agent, solvent, and microcapsules in step 2) is 5-8 g: 20-30 g: 0.3-1 g: 3-5 g: 40-50 mL: 3-5 g.

[0013] Preferably, the temperature of the photocuring in step 2) is 20-30 °C, and the wavelength of the light source for photocuring is 200-315 nm; The sterilization method is to soak and sterilize with a bactericide, and the bactericide is a solution containing polyhexamethylene guanidine, polyquaternium-1, and a complexing agent, wherein the concentration of polyhexamethylene guanidine is 0.0001-0.0002 wt%, the concentration of polyquaternium-1 is 0.001-0.004 wt%, and the concentration of the complexing agent is 0.01-0.1 wt%; The complexing agent is one or more of ethylenediaminetetraacetic acid, sodium citrate, and sodium pyrophosphate.

[0014] The present invention also provides a photocurable contact lens containing microcapsules prepared by the above preparation method.

[0015] The present invention has at least the following beneficial effects: The present invention uses polymethyl methacrylate as the outer wall material of the microcapsules. The light transmittance of this material can reach 92%, and it has a refractive index similar to that of the contact lens matrix material mainly composed of polyacrylate, which will not affect the light transmittance and wearing comfort of the final product; using this material to coat the plant extracts of salvianolic acid and calenduloside A, which have bactericidal and fragrant effects, enables the contact lens to have a certain bactericidal effect during wearing and avoids the growth of bacteria on the surface of the contact lens; and the encapsulated sodium hyaluronate has excellent moisturizing effects, improving the wearing comfort of the contact lens. Specific embodiments

[0016] The present invention provides a preparation method of a photocurable contact lens containing microcapsules, including the following steps: 1) Mix carnosol, calenduloside, sodium hyaluronate, ethanol and water to obtain a core material mixture solution. Under stirring conditions, mix the core material mixture solution with polymethyl methacrylate solution and perform ultrasonic treatment to form an emulsion, and then spray-dry the emulsion to obtain microcapsules. 2) Mix silicone monomers, acrylate monomers, photoinitiators, crosslinkers, solvents and the microcapsules prepared in step 1), and then successively perform mold injection, photocuring, soaking, and sterilization to obtain photocured contact lenses containing microcapsules.

[0017] In the present invention, in the core material mixture solution in step 1), the concentration of carnosol is 0.5 - 1.0 wt%, preferably 0.6 - 0.9 wt%, further preferably 0.7 - 0.8 wt%, and more preferably 0.75 wt%; the concentration of calenduloside is 0.2 - 1.2 wt%, preferably 0.3 - 1.0 wt%, further preferably 0.4 - 0.8 wt%, and more preferably 0.5 - 0.6 wt%; the concentration of sodium hyaluronate is 0.8 - 1.5 wt%, preferably 0.9 - 1.4 wt%, further preferably 1.0 - 1.3 wt%, and more preferably 1.1 - 1.2 wt%.

[0018] In the present invention, the volume ratio of ethanol to water is 1 - 3:97 - 99, preferably 1.5 - 2.5:97.5 - 98.5, and further preferably 2:98.

[0019] In the present invention, the mixing order of carnosol, calenduloside, sodium hyaluronate, ethanol and water is to dissolve carnosol in ethanol, dissolve calenduloside and sodium hyaluronate in water, and then mix the two to obtain a core material mixture solution.

[0020] In the present invention, in step 1), the concentration of the polymethyl methacrylate solution is 3 - 6 wt%, preferably 3.5 - 5.5 wt%, further preferably 4 - 5 wt%, and more preferably 4.5 wt%; the solvent is acetone.

[0021] In the present invention, in step 1), the volume ratio of the core material mixture solution to the polymethyl methacrylate solution is 1:1 - 1.2, preferably 1:1.05 - 1.15, and further preferably 1:1.1.

[0022] In the present invention, the frequency of the ultrasonic treatment is 20 - 30 kHz, preferably 22 - 28 kHz, further preferably 24 - 26 kHz, and more preferably 25 kHz; the time of the ultrasonic treatment is 5 - 15 min, preferably 7 - 12 min, and further preferably 10 min.

[0023] In the present invention, the temperature of the spray drying is 70~120°C, preferably 75~110°C, more preferably 80~100°C, and even more preferably 85~90°C.

[0024] In the present invention, in step 1), the particle size of the microcapsules is 50~150 nm, preferably 55~120 nm, more preferably 60~100 nm, and even more preferably 65~80 nm.

[0025] In the present invention, in step 2), the organosilicon monomers include one or more of 3-methacryloyloxypropyl-tris-(trimethylsiloxy)silane, methacryloxymethyltriethoxysilane, γ-(methacryloyloxy)propyltrimethoxysilane, 2-methylacrylic acid (pentamethyldisiloxanyl) methyl ester, and 3-(trimethoxysilyl)propyl methacrylate; In the present invention, the acrylate monomers include one or more of 2-hydroxyethyl methacrylate, methyl methacrylate, ethyl acrylate, and glycidyl methacrylate.

[0026] In the present invention, the photoinitiator includes one or more of 2-hydroxy-2-methyl-1-phenyl-1-propanone, 2-hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone, and phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide.

[0027] In the present invention, the crosslinking agent includes one or more of ethylene glycol dimethacrylate, trimethylolpropane trimethacrylate, and 2-methacryloyloxyethyl phosphorylcholine.

[0028] In the present invention, the solvent includes one or more of N,N-dimethylformamide, acetone, isopropyl alcohol, and ethylene glycol.

[0029] In the present invention, in step 2), the mixing ratio of the organosilicon monomer, acrylate monomer, photoinitiator, crosslinking agent, solvent, and microcapsules is 5~8 g: 20~30 g: 0.3~1 g: 3~5 g: 40~50 mL: 3~5 g, preferably 5.5~7.5 g: 22~28 g: 0.4~0.9 g: 3.5~4.5 g: 42~48 mL: 3.3~4.8 g, more preferably 6~7 g: 24~26 g: 0.5~0.8 g: 3.7~4.3 g: 44~46 mL: 3.5~4.5 g, and even more preferably 6.3~6.7 g: 25 g: 0.6~0.7 g: 4 g: 45 mL: 3.8~4 g.

[0030] In the present invention, in step 2), the temperature of the photocuring is 20~30°C, preferably 22~28°C, more preferably 25°C; the wavelength of the light source for photocuring is 200~315 nm.

[0031] In the present invention, the sterilization method is soaking sterilization with a bactericide, and the bactericide is a solution containing polyhexamethylene guanidine, polyquaternium-1 and a complexing agent. The concentration of polyhexamethylene guanidine is 0.0001 - 0.0002 wt%, preferably 0.00012 - 0.00018 wt%, more preferably 0.00014 - 0.00016 wt%, and even more preferably 0.00015 wt%; the concentration of polyquaternium-1 is 0.001 - 0.004 wt%, preferably 0.0015 - 0.0035 wt%, more preferably 0.002 - 0.003 wt%, and even more preferably 0.0025 wt%; the concentration of the complexing agent is 0.01 - 0.1 wt%, preferably 0.02 - 0.08 wt%, more preferably 0.04 - 0.06 wt%, and even more preferably 0.05 wt%. This bactericide has broad-spectrum bactericidal properties, and will not damage the outer wall material of the microcapsules, nor will it affect the crosslinking degree of the contact lens matrix material.

[0032] In the present invention, the complexing agent is one or more of ethylenediaminetetraacetic acid, sodium citrate and sodium pyrophosphate.

[0033] The present invention also provides a photocurable contact lens containing microcapsules prepared by the above preparation method.

[0034] The technical solutions provided by the present invention will be described in detail below in conjunction with the embodiments, but they should not be construed as limiting the protection scope of the present invention.

[0035] Example 1 (1) Take 1 g of salvigenol and dissolve it in 2 mL of ethanol, 1 g of calenduloside saponin, and 1.5 g of sodium hyaluronate (molecular weight 800 - 2000 kDa) and mix with 100 mL of water. Mix the ethanol solution of salvigenol with the aqueous solutions of calenduloside and sodium hyaluronate to obtain a core material mixture; dissolve 5 g of polymethyl methacrylate (average molecular weight 350000) in 100 mL of acetone to obtain an outer wall material solution; mix the core material mixture with the outer wall material solution (stir at 2000 r / min for 3 * 0 min), then perform ultrasonic treatment at a frequency of 25 kHz for 15 min at room temperature (25 °C) to obtain a uniform emulsion. Add 5 mL of a 1 wt% Tween 80 solution to stabilize the emulsion, then pass the emulsion through a microporous membrane with a pore size of 20 μm, and then use a spray dryer for drying. The pressure at the nozzle is 40 MPa, and the drying temperature is 80 °C. The particle size range of the obtained microcapsules is 50 - 80 nm.

[0036] (2) Mix 3-methacryloxypropyl-tris-(trimethylsiloxy)silane, 2-hydroxyethyl methacrylate, 2-hydroxy-2-methyl-1-phenyl-1-propanone, ethylene glycol dimethacrylate and N,N-dimethylformamide in a ratio of 5 g: 25 g: 0.3 g: 3 g: 50 mL: 5 g to obtain a contact lens precursor solution; inject the contact lens precursor solution into a contact lens mold and perform photocuring molding under medium and short wave ultraviolet light of 200 - 315 nm to obtain a contact lens, where the temperature of photocuring molding is 25 °C and the time is 3 min.

[0037] First, soak the contact lens in isopropanol for 30 min to wash away residual organic substances (unreacted monomers); then wash the contact lens with ultrapure water 5 times, soak it in PBS buffer solution (pH value is 7.2) for 8 h, and finally soak it in a bactericide (the concentration of polyhexamethylene guanidine is 0.0001 wt%, the concentration of polyquaternium-1 is 0.001 wt%, the concentration of EDTA is 0.05 wt%, and the pH value of the system is adjusted to 7.2 with TRIS-HCl) for 1 h for sterilization to obtain a photocured contact lens product containing microcapsules.

[0038] Example 2 (1) Dissolve 0.8 g of salvigenol in 2 mL of ethanol, then dissolve 0.5 g of calenduloside saponin and 1 g of sodium hyaluronate (molecular weight 800 - 2000 kDa) in 98 mL of water, and mix the ethanol solution of salvigenol with the aqueous solutions of calenduloside and sodium hyaluronate to obtain a core material mixture solution; dissolve 4 g of polymethyl methacrylate (average molecular weight 350000) in 100 mL of acetone to obtain an outer wall material solution; mix the core material mixture solution with the outer wall material solution (stir at 2200 r / min for 30 min), then perform ultrasonic treatment at a frequency of 20 kHz for 15 min at room temperature (25 °C) to obtain a uniform emulsion, add 5 mL of a 1 wt% Tween 80 solution to stabilize the emulsion, pass the emulsion through a microporous membrane with a pore size of 20 μm, and then dry it with a spray dryer, where the pressure at the nozzle is 40 MPa and the drying temperature is 70 °C, and the particle size range of the obtained microcapsules is 60 - 100 nm.

[0039] (2) Mix (2-pentamethyldisiloxanyl)methyl methacrylate, ethyl acrylate, 2-hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone, 2-methacryloyloxyethyl phosphorylcholine and N,N-dimethylformamide in a ratio of 8 g: 28 g: 0.5 g: 3.5 g: 50 mL: 4 g to obtain a contact lens precursor solution; inject the contact lens precursor solution into a contact lens mold and perform photocuring molding under medium and short wave ultraviolet light of 200 - 315 nm to obtain a contact lens, where the temperature of photocuring molding is 25 °C and the time is 3 min.

[0040] First, soak the contact lenses in isopropanol for 30 min to wash away the residual organic matter (unreacted monomers); then wash the contact lens lenses 5 times with ultrapure water and soak them in a PBS buffer solution (pH value of 7.2) for 8 h. Finally, soak them in a bactericide (the concentration of polyhexamethylene guanidine is 0.0001 wt%, the concentration of polyquaternium-1 is 0.003 wt%, the concentration of EDTA is 0.05 wt%, and the pH value of the system is adjusted to 7.2 with TRIS-HCl) for 1 h for sterilization to obtain a photocurable contact lens product containing microcapsules.

[0041] Example 3 (1) Dissolve 0.5 g of salvigenol in 2 mL of ethanol. Then dissolve 1.2 g of calenduloside saponin and 0.8 g of sodium hyaluronate (molecular weight 800 - 2000 kDa) in 98 mL of water. Mix the ethanol solution of salvigenol with the aqueous solutions of calenduloside and sodium hyaluronate to obtain a core material mixture solution; dissolve 5 g of polymethyl methacrylate (average molecular weight 350000) in 100 mL of acetone to obtain an outer wall material solution; mix the core material mixture solution with the outer wall material solution (stir at 2500 r / min for 30 min), then perform ultrasonic treatment at a frequency of 28 kHz for 15 min at room temperature (25 °C) to obtain a uniform emulsion. Add 5 mL of a 1 wt% Tween 80 solution to stabilize the emulsion, then pass the emulsion through a microporous membrane with a pore size of 20 μm, and then dry it using a spray dryer. The pressure at the nozzle is 40 MPa and the drying temperature is 100 °C. The particle size range of the obtained microcapsules is 50 - 65 nm.

[0042] (2) Mix methacryloxymethyltriethoxysilane, glycidyl methacrylate, phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, 2-methacryloyloxyethyl phosphorylcholine, and N,N-dimethylformamide in a ratio of 8 g:20 g:1 g:5 g:40 mL:3 g to obtain a contact lens precursor solution; inject the contact lens precursor solution into a contact lens mold and perform photocuring molding under medium and short-wave ultraviolet light of 200 - 315 nm to obtain a contact lens lens. The temperature of photocuring molding is 25 °C and the time is 3 min.

[0043] First, soak the contact lenses in isopropanol for 30 min to wash away the residual organic matter (unreacted monomers); then wash the contact lens with ultrapure water 5 times, soak it in PBS buffer solution (pH value is 7.2) for 8 h, and finally soak it in a bactericide (the concentration of polyhexamethylene guanidine is 0.0001 wt%, the concentration of polyquaternium-1 is 0.001 wt%, the concentration of EDTA is 0.05 wt%, and the pH value of the system is adjusted to 7.2 with TRIS-HCl) for 1 h for sterilization to obtain a photocurable contact lens product containing microcapsules.

[0044] Example 4 (1) Dissolve 1 g of salvigenin in 2 mL of ethanol, then dissolve 1 g of calenduloside saponin and 1.5 g of sodium hyaluronate (molecular weight 800 - 2000 kDa) in 98 mL of water, and mix the ethanol solution of salvigenin with the aqueous solutions of calenduloside and sodium hyaluronate to obtain a core material mixture solution; dissolve 5 g of polymethyl methacrylate (average molecular weight 350000) in 100 mL of acetone to obtain an outer wall material solution; mix the core material mixture solution with the outer wall material solution (stir at 2000 r / min for 30 min), then perform ultrasonic treatment at a frequency of 25 kHz for 15 min at room temperature (25 °C) to obtain a uniform emulsion, add 5 mL of a 1 wt% Tween 80 solution to stabilize the emulsion, then pass the emulsion through a microporous membrane with a pore size of 20 μm, and then dry it using a spray dryer with a pressure of 40 MPa at the nozzle and a drying temperature of 80 °C to obtain microcapsules with a particle size range of 50 - 80 nm.

[0045] (2) Mix γ-(methacryloyloxy)propyltrimethoxysilane, ethyl acrylate, 2-hydroxy-2-methyl-1-phenyl-1-propanone, trimethylolpropane trimethacrylate and N,N-dimethylformamide in a ratio of 7 g:24 g:0.4 g:3.7 g:42 mL:3.8 g to obtain a contact lens precursor solution; inject the contact lens precursor solution into a contact lens mold and perform photocuring molding under medium and short wave ultraviolet light of 200 - 315 nm to obtain a contact lens, the temperature of photocuring molding is 25 °C and the time is 3 min.

[0046] First, soak the contact lenses in isopropanol for 30 min to wash away the residual organic matter (unreacted monomers); then wash the contact lens with ultrapure water 5 times, soak it in PBS buffer solution (pH value is 7.2) for 8 h, and finally soak it in a bactericide (the concentration of polyhexamethylene guanidine is 0.0001 wt%, the concentration of polyquaternium-1 is 0.001 wt%, the concentration of EDTA is 0.05 wt%, and the pH value of the system is adjusted to 7.2 with TRIS-HCl) for 1 h for sterilization to obtain a photocurable contact lens product containing microcapsules.

[0047] Example 5 (1) Dissolve 0.75 g of salvigenol in 2 mL of ethanol, and then dissolve 0.6 g of calenduloside saponin and 0.9 g of sodium hyaluronate (molecular weight 800 - 2000 kDa) in 98 mL of water. Mix the ethanol solution of salvigenol with the aqueous solutions of calenduloside and sodium hyaluronate to obtain a core material mixture solution; dissolve 6 g of polymethyl methacrylate (average molecular weight 350000) in 100 mL of acetone to obtain an outer wall material solution; mix the core material mixture solution with the outer wall material solution (stir at 2000 r / min for 30 min), then perform ultrasonic treatment at a frequency of 25 kHz for 15 min at room temperature (25 °C) to obtain a uniform emulsion. Add 5 mL of a 1 wt% Tween 80 solution to stabilize the emulsion, then pass the emulsion through a microporous membrane with a pore size of 20 μm, and then use a spray dryer for drying. The pressure at the nozzle is 40 MPa, and the drying temperature is 80 °C. The particle size range of the obtained microcapsules is 50 - 90 nm.

[0048] (2) Mix 3 - methacryloxypropyl - tris - (trimethylsiloxysilane), 2 - hydroxyethyl methacrylate, 2 - hydroxy - 2 - methyl - 1 - phenyl - 1 - propanone, ethylene glycol dimethacrylate and N,N - dimethylformamide in a ratio of 6.3 g:24 g:0.6 g:4 g:45 mL:3.8 g to obtain a contact lens precursor solution; inject the contact lens precursor solution into a contact lens mold and perform photocuring molding under medium - short wave ultraviolet light of 200 - 315 nm to obtain a contact lens lens. The temperature of photocuring molding is 25 °C and the time is 3 min.

[0049] First, soak the contact lens in isopropanol for 30 min to wash away residual organic substances (unreacted monomers); then wash the contact lens lens 5 times with ultrapure water, soak it in a PBS buffer solution (pH value 7.2) for 8 h, and finally soak it in a bactericide (the concentration of polyhexamethyl guanidine is 0.0001 wt%, the concentration of polyquaternium - 1 is 0.001 wt%, the concentration of EDTA is 0.05 wt%, and the pH value of the system is adjusted to 7.2 with TRIS - HCl) for 1 h for sterilization to obtain a photocured contact lens product containing microcapsules.

[0050] Test the performance of the photocured contact lenses containing microcapsules prepared in Examples 1 - 5. The test methods are as follows: 1. Cytotoxicity test Perform cytotoxicity tests on the photocured contact lenses containing microcapsules prepared in Examples 1 - 5 according to standard ISO9363 - 1. The toxicity reaction grades are shown in Table 1.

[0051] 2. Water content test The water content of the photocurable contact lenses containing microcapsules prepared in Examples 1 to 5 was tested according to the "Heavy Method for Measuring the Water Content / Evaporation Loss of Hydrogel Contact Lenses" described in Section 4.5 of Standard GB / T 11417.7-2012. The test results are shown in Table 1.

[0052] 3. Oxygen permeability test The oxygen permeability of the photocurable contact lenses containing microcapsules prepared in Examples 1 to 5 was tested by the polarographic method described in Section 4.4.3 of Standard GB / T 11417.7-2012. The test results are shown in Table 1 (unit: 10 -11 (cm 2 / s)·[mLO2 / (mL·hPa)]).

[0053] 4. Light transmittance test The refractive index of the photocurable contact lenses containing microcapsules prepared in Examples 1 to 5 was tested according to the test method described in Section 4.4, refractive index, of Standard GB / T 11417.7-2012. The test results are shown in Table 1.

[0054] 5. Contact angle test The contact angle of the photocurable contact lenses containing microcapsules prepared in Examples 1 to 5 was tested according to the test method described in Section 4.6, contact angle, of Standard GB / T 11417.7-2012. The test results are shown in Table 1.

[0055] Table 1 Performance test results of the photocurable contact lenses containing microcapsules prepared in Examples 1 to 5 Test items Cytotoxicity Water content Oxygen permeability Light transmittance (wet body) Contact angle Example 1 0 47.3% 75 92% 53° Example 2 0 48.0% 73 91% 49° Example 3 0 48.8% 81 88% 50° Example 4 0 47.6% 78 89% 52° Example 5 0 48.2% 75 91% 50° It can be seen from the data in Table 1 that the contact lenses prepared in the examples of this application have high transparency and will not reduce the transparency due to the introduction of microcapsules. For contact lenses, the wearing comfort is relatively high when the contact angle is 49°. The contact lenses prepared in Examples 1 to 5 are all around 49°, and a stable tear film can be formed during wearing, improving the wearing comfort. The oxygen permeability is above 25 Dk / t of the national standard.

[0056] The antibacterial properties of the photocurable contact lenses containing microcapsules prepared in Examples 1 to 5 were tested according to the method described in Section 2.3.2 of GB19192-2003. The test results are shown in Table 2.

[0057] Table 2 Antibacterial property test results of the photocurable contact lenses containing microcapsules prepared in Examples 1 to 5 Bacterial species Escherichia coli Staphylococcus aureus Pseudomonas aeruginosa Example 1 ≥99.9% ≥99.9% ≥99.9% Example 2 ≥99.9% ≥99.9% ≥99.9% Example 3 ≥99.9% ≥99.9% ≥99.9% Example 4 ≥99.9% ≥99.9% ≥99.9% Example 5 ≥99.9% ≥99.9% ≥99.9% The test results according to Table 2 show that the photocurable contact lenses containing microcapsules prepared in Examples 1 to 5 have excellent antibacterial properties, indicating that carnosol and marigold saponins inside the microcapsules can play an antibacterial role through the outer wall material of the microcapsules during wearing, and carnosol has a delicate fragrance and can be released continuously and slowly.

[0058] The above are only the preferred embodiments of the present invention. It should be noted that for those of ordinary skill in the art, without departing from the principle of the present invention, several improvements and refinements can be made, and these improvements and refinements should also be regarded as the protection scope of the present invention.

Claims

1. A preparation method of a microcapsule-containing photocurable contact lens, characterized in that, It includes the following steps: 1) Mix salvigenol, calenduloside, sodium hyaluronate, ethanol and water to obtain a core material mixture solution. Under stirring conditions, mix the core material mixture solution with a polymethyl methacrylate solution and perform ultrasonic treatment to form an emulsion. Spray-dry the emulsion to obtain microcapsules; 2) Mix an organosilicon monomer, an acrylate monomer, a photoinitiator, a crosslinking agent, a solvent and the microcapsules prepared in step 1), and then successively perform mold injection, photocuring, soaking and sterilization to obtain a photocured contact lens containing microcapsules.

2. The preparation method of a photo-curable contact lens containing microcapsules according to claim 1, characterized in that, In step 1), the concentration of salvigenol in the core material mixture solution is 0.5 - 1.0 wt%, the concentration of calenduloside is 0.2 - 1.2 wt%, and the concentration of sodium hyaluronate is 0.8 - 1.5 wt%; The volume ratio of the ethanol to the water is 1 - 3:97 - 99.

3. The preparation method of a photo-curable contact lens containing microcapsules according to claim 2, characterized in that, In step 1), the concentration of the polymethyl methacrylate solution is 3 - 6 wt%, and the solvent is acetone.

4. The preparation method of a photocurable contact lens containing microcapsules according to any one of claims 1 to 3, characterized in that In step 1), the volume ratio of the core material mixture solution to the polymethyl methacrylate solution is 1:1 - 1.2; The frequency of the ultrasonic treatment is 20 - 30 kHz, and the time of the ultrasonic treatment is 5 - 15 min; The temperature of the spray drying is 70 - 120 °C.

5. The preparation method of a photo-curable contact lens containing microcapsules according to claim 4, characterized in that, In step 1), the particle size of the microcapsules is 50 - 150 nm.

6. The preparation method of a photocurable contact lens containing microcapsules according to claim 5, characterized in that, In step 2), the organosilicon monomer includes one or more of 3-methacryloyloxypropyl-tris-(trimethylsiloxy)silane, methacryloxymethyltriethoxysilane, γ-(methacryloyloxy)propyltrimethoxysilane, 2-methacrylic acid (pentamethyldisiloxanyl) methyl ester and 3-(trimethoxysilyl)propyl methacrylate; The acrylate monomer includes one or more of 2-hydroxyethyl methacrylate, methyl methacrylate, ethyl acrylate and glycidyl methacrylate; The photoinitiator includes one or more of 2-hydroxy-2-methyl-1-phenyl-1-propanone, 2-hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone and phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide; The crosslinking agent includes one or more of ethylene glycol dimethacrylate, trimethylolpropane trimethacrylate and 2-methacryloyloxyethyl phosphorylcholine; The solvent includes one or more of N,N-dimethylformamide, acetone, isopropanol and ethylene glycol.

7. The preparation method of a photocurable contact lens containing microcapsules according to claim 6, characterized in that, In step 2), the mixing ratio of the organosilicon monomer, acrylate monomer, photoinitiator, crosslinking agent, solvent and microcapsules is 5 - 8 g:20 - 30 g:0.3 - 1 g:3 - 5 g:40 - 50 mL:3 - 5 g.

8. The preparation method of a photo-curable contact lens containing microcapsules according to claim 7, characterized in that, In step 2), the temperature of the photocuring is 20 - 30 °C, and the wavelength of the light source for photocuring is 200 - 315 nm; The sterilization method is soaking sterilization with a bactericide. The bactericide is a solution containing polyhexamethylene guanidine, polyquaternium-1 and a complexing agent, wherein the concentration of polyhexamethylene guanidine is 0.0001 - 0.0002 wt%, the concentration of polyquaternium-1 is 0.001 - 0.004 wt%, and the concentration of the complexing agent is 0.01 - 0.1 wt%; The complexing agent is one or more of ethylenediaminetetraacetic acid, sodium citrate, and sodium pyrophosphate.

9. A photocurable contact lens containing microcapsules prepared by the method for preparing a photocurable contact lens containing microcapsules according to any one of claims 1 to 8.