Photocuring material, preparation method thereof and contact lens

Abstract

The invention relates to the technical field of biological materials, in particular to a photocuring material, a preparation method of the photocuring material and contact lenses, and the photocuring material comprises the following raw material components in parts by weight: 0.1-5 parts of polymerizable poly-beta-serine; 10-30 parts of a hydrophobic monomer; 60 to 80 parts of a hydrophilic monomer; 1-7 parts of an ultraviolet absorbent; and 0.1 to 3 parts of a photoinitiator. According to the photocuring material provided by the invention, by introducing the polymerizable poly-beta-serine into the raw materials, when the prepared photocuring material is used for contact lenses, protein adsorption and microbial adhesion can be effectively reduced, so that the antibacterial property of the contact lenses can be improved while the precipitate adsorption resistance of the contact lenses is improved; and the service life of the contact lens can be prolonged.

Description

Technical Field

[0001] The present invention relates to the technical field of biomaterials, and in particular to a photocurable material and a preparation method thereof, and a contact lens. Background Art

[0002] Contact lenses, also known as corneal contact lenses, have been widely used in vision correction, vision protection, and ophthalmic surgery auxiliary treatment. "Phakic posterior chamber intraocular lens" (foreign abbreviation: ICL, foreign full name: Implantable Collamer Lens) is a safe and high-end myopia correction solution. Unlike laser and other surgeries that cut corneal tissue, it does not cut the cornea. The lens is implanted into the eye through minimally invasive surgery without damaging the cornea. After correction, the vision is clearer, which is a new trend in myopia correction technology.

[0003] Since contact lenses need to come into contact with the human cornea during wear, the materials used to make contact lenses are required to be non-toxic to the human body and have good biocompatibility and oxygen permeability.

[0004] Traditional contact lenses are mainly made of poly(hydroxyethyl methacrylate) materials. Contact lenses made of this material are soft and comfortable, but contact lenses made of this material, especially ICL, are prone to adsorb sediment during wear, resulting in a shorter service life and limiting the use of contact lenses. In particular, when ICL is implanted in the body, it is more likely to produce protein adsorption, causing the ICL to become blurred and affecting the use effect. Summary of the invention

[0005] In order to solve the problem that contact lenses are prone to adsorbing precipitates in the prior art, the present invention provides a photocurable material. The photocurable material introduces polymerizable poly-β-serine so that the photocurable material has excellent anti-adhesion properties. When used for contact lenses, the photocurable material can effectively resist the adsorption of various proteins, thereby solving the problem that contact lenses are prone to adsorbing precipitates in the prior art.

[0006] The technical solution adopted by the present invention to solve its technical problem is: A photocurable material, wherein the raw materials include the following components in parts by weight: 0.1-5 parts of polymerizable poly-β-serine; 10-30 parts of hydrophobic monomer; 60-80 parts of hydrophilic monomer; 1-7 parts of ultraviolet absorber; Photoinitiator 0.1-3 parts.

[0007] Optionally, the polymerizable poly-β-serine is prepared according to the following method: S1: preparing acrylic acid-modified poly-β-serine using poly-β-serine and acryloyl chloride as raw materials; S2: dissolving the acrylic acid-modified poly-β-serine in dimethyl sulfoxide, adding n-butylamine dropwise, and reacting at 60° C. to obtain a first reaction solution; S3: adding 2-bromoethyl acrylate to the first reaction solution, reacting at 50° C. to obtain a second reaction solution; S4: adding the second reaction solution into diethyl ether, filtering, precipitating, and washing to obtain polymerizable poly-β-serine.

[0008] Optionally, the molar ratio of the poly-β-serine, the acryloyl chloride, the n-butylamine, and the 2-bromoethyl acrylate is in the range of 1:(6-10):(6-10):(6-10).

[0009] Optionally, preparing acrylic acid-modified poly-β-serine using poly-β-serine and acryloyl chloride as raw materials comprises: S11: mixing poly-β-serine, triethylamine and anhydrous tetrahydrofuran to obtain a first solution; S12: mixing acryloyl chloride and anhydrous tetrahydrofuran to obtain a second solution; S13: at 0° C. and in an inert gas atmosphere, dropping the second solution into the first solution, and reflux reaction to obtain a reaction solution; S14: adding the reaction solution into ethanol, filtering, precipitating, and washing to obtain acrylic acid-modified poly-β-serine.

[0010] Optionally, the hydrophobic monomer is selected from at least one of 2-hydroxy-4-(methacryloyloxy)benzophenone, ethyl 3-benzoylacrylate, 3-allyl-4-hydroxyacetophenone, 2-(2-hydroxy-3-allyl-5-methylphenyl)-2H-benzotriazole, n-propyl methacrylate, allylbenzene, allyl butyrate, allyl anisole, ethyl methacrylate, methyl methacrylate, and n-heptyl methacrylate.

[0011] Optionally, the hydrophilic monomer is selected from at least one of 2-hydroxyethyl methacrylate, hydroxypropyl methacrylate, allyl alcohol, polyethylene glycol monomethyl ether methacrylate, 4-hydroxybutyl methacrylate, and allyl glycol carbonate.

[0012] Optionally, the ultraviolet absorber is selected from at least one of 2-(2-hydroxy-3-allyl-5-methylphenyl)-2H-benzotriazole, 2-(2-hydroxy-5-methylphenyl)benzotriazole, 2-hydroxy-4-acryloyloxyethoxybenzotriazole, 2-hydroxy-4-alkoxybenzophenone and substituted acrylonitrile.

[0013] Optionally, the photoinitiator is selected from at least one of 184, 1173, TPO, TPO-L, 819, 2959, and LAP.

[0014] Another object of the present invention is to provide a method for preparing the photocurable material as described above, comprising the following steps: mixing a hydrophilic monomer, a hydrophobic monomer, a UV absorber, and a polymerizable poly-β-serine according to the formula amount, adding a photoinitiator, and polymerizing by ultraviolet light to obtain a photocurable material.

[0015] Another object of the present invention is to provide a contact lens prepared by the photocurable material as described above.

[0016] Optionally, a phakic posterior chamber intraocular lens is included.

[0017] The beneficial effects of the present invention are: The photocurable material provided by the present invention introduces polymerizable poly-β-serine into the raw material, so that when the prepared photocurable material is used for contact lenses, it can effectively reduce protein adsorption and microbial adhesion, thereby improving the anti-precipitate adsorption performance of the contact lenses while improving their antibacterial properties, which helps to extend the service life of the contact lenses. DETAILED DESCRIPTION

[0018] The present invention is now further described in detail. The embodiments described below are exemplary and intended to be used to explain the present invention, but cannot be understood as limiting the present invention. All other embodiments obtained by ordinary technicians in this field without creative work based on the embodiments of the present invention belong to the scope of protection of the present invention.

[0019] In order to solve the problem that contact lenses are prone to adsorbing precipitates in the prior art, the present invention provides a photocurable material, wherein the raw materials include the following components in parts by weight: 0.1-5 parts of polymerizable poly-β-serine; 10-30 parts of hydrophobic monomer; 60-80 parts of hydrophilic monomer; 1-7 parts of ultraviolet absorber; Photoinitiator 0.1-3 parts.

[0020] The main components of the precipitates on the contact lenses are various proteins related to tears; poly-β-serine has the characteristics of good biocompatibility and high stability, and can effectively resist the adsorption of multiple proteins and the adhesion of multiple microorganisms; by introducing polymerizable poly-β-serine into the raw materials, the polymerizable poly-β-serine can participate in the polymerization reaction, and the poly-β-serine is introduced into the prepared photocurable material through chemical bonds, thereby introducing poly-β-serine, while ensuring the excellent biocompatibility of the photocurable material, improving its anti-protein adsorption and anti-microbial adhesion performance, and thus making the contact lenses prepared by the photocurable material can effectively resist protein adsorption and anti-microbial adhesion, while avoiding precipitate adsorption, while improving antibacterial performance; especially for the case where ICL is implanted in the body, it can effectively resist protein adsorption while ensuring safety, improve the use effect, and extend the service life.

[0021] The photocurable material provided by the present invention introduces polymerizable poly-β-serine into the raw material, so that when the prepared photocurable material is used for contact lenses, it can effectively reduce protein adsorption and microbial adhesion, thereby improving the anti-precipitate adsorption performance of the contact lenses while improving their antibacterial properties, which helps to extend the service life of the contact lenses.

[0022] The preferred polymerizable poly-β-serine of the present invention is prepared according to the following method: S1: preparing acrylic acid-modified poly-β-serine using poly-β-serine and acryloyl chloride as raw materials; S2: dissolving acrylic acid-modified poly-β-serine in dimethyl sulfoxide, adding n-butylamine dropwise, and reacting at 60° C. to obtain a first reaction solution; S3: adding 2-bromoethyl acrylate to the first reaction solution, reacting at 50° C. to obtain a second reaction solution; S4: adding the second reaction solution into ether, filtering, precipitating, and washing to obtain polymerizable poly-β-serine.

[0023] In the preparation method, the target product, polymerizable poly-β-serine, can be obtained through acylation reaction, Michael addition reaction and nucleophilic substitution reaction in sequence. The reaction process is simple, easy to operate and the reaction conditions are mild.

[0024] The reaction process is as follows: ; Here, n is a natural number greater than 1.

[0025] The polymerizable poly-β-serine provided by the present invention maintains the anti-protein adhesion of the poly-β-serine after the poly-β-serine is modified, and at the same time has the antibacterial property of the quaternary ammonium salt.

[0026] In order to take into account the anti-protein adhesion performance, antibacterial property and economy, the molar ratio of poly-β-serine, acryloyl chloride, n-butylamine and 2-bromoethyl acrylate in the preferred preparation process of the present invention is 1: (6-10): (6-10): (6-10).

[0027] Among them, the method of preparing acrylic acid-modified poly-β-serine using poly-β-serine and acryloyl chloride as raw materials preferably includes: S11: mixing poly-β-serine, triethylamine and anhydrous tetrahydrofuran to obtain a first solution; S12: mixing acryloyl chloride and anhydrous tetrahydrofuran to obtain a second solution; S13: at 0° C. and in an inert gas atmosphere, dropwise adding the second solution into the first solution, and reflux reaction to obtain a reaction solution; S14: adding the reaction solution into ethanol, filtering, precipitating, and washing to obtain acrylic acid-modified poly-β-serine.

[0028] Specifically, the polymerizable poly-β-serine of the present invention is preferably prepared according to the following process: S1: Preparation of acrylic acid-modified poly-β-serine using poly-β-serine and acryloyl chloride as raw materials: S11: A magnetic stirring bar is provided in a double-necked flat-bottomed flask, and poly-β-serine, TEA, and anhydrous THF are added into the double-necked flat-bottomed flask and mixed to obtain a first solution; S12: adding acryloyl chloride to anhydrous THF and mixing to obtain a second solution; S13: at 0° C. and in an inert gas atmosphere, dropwise adding the second solution into the first solution, and reflux reacting, preferably reflux reacting for 24 hours, to obtain a reaction solution; S14: slowly adding the reaction solution into ethanol, filtering, precipitating, and washing, preferably washing with ethanol three times, to obtain acrylic acid-modified poly-β-serine; S2: dissolving acrylic acid-modified poly-β-serine in dimethyl sulfoxide (DMSO) (preferably, the mass concentration of acrylic acid-modified poly-β-serine after dissolution is 1-15%), slowly adding n-butylamine, stirring and reacting at 60° C., preferably stirring and reacting for 12 hours, until the double bonds are completely reacted, to obtain a first reaction solution; S3: adding 2-bromoethyl acrylate to the first reaction solution, stirring at 50° C. overnight, and obtaining a second reaction solution after the reaction is completed; S4: slowly adding the second reaction solution into diethyl ether, filtering, precipitating, and washing, preferably washing with diethyl ether three times, to obtain polymerizable poly-β-serine.

[0029] The polymerizable poly-β-serine prepared by the method can be copolymerized with hydrophobic monomers and hydrophilic monomers, so that the prepared copolymer has excellent anti-protein adhesion and antibacterial properties, thereby improving the anti-precipitate adsorption performance and extending the service life of contact lenses.

[0030] In order to take into account the biocompatibility, optical properties and wearing comfort of the contact lens, the present invention preferably uses a hydrophobic monomer as a hydrophobic acrylic monomer or a hydrophobic allele monomer, wherein the hydrophobic acrylic monomer refers to any water-insoluble monomer containing an acrylic group; the hydrophobic allele monomer refers to any water-insoluble monomer containing an allyl group; and further preferably, the hydrophobic monomer includes at least one hydrophobic acrylic monomer or hydrophobic allele monomer that absorbs ultraviolet light; specifically, the present invention preferably uses a hydrophobic monomer selected from at least one of 2-hydroxy-4-(methacryloyloxy)benzophenone (HMBP), ethyl 3-benzoylacrylate (EBA), 3-allyl-4-hydroxyacetophenone, 2-(2-hydroxy-3-allyl-5-methylphenyl)-2H-benzotriazole, n-propyl methacrylate, allylbenzene, allyl butyrate, allyl anisole, ethyl methacrylate, methyl methacrylate (MMA), and n-heptyl methacrylate.

[0031] The preferred hydrophilic monomer of the present invention is a hydrophilic acrylic monomer or a hydrophilic allele monomer, wherein the hydrophilic acrylic monomer refers to any water-soluble monomer containing an acrylic group; the hydrophilic allele monomer refers to any water-soluble monomer containing an allyl group; specifically, the preferred hydrophilic monomer is at least one selected from 2-hydroxyethyl methacrylate (HEMA), hydroxypropyl methacrylate (HPMA), allyl alcohol, polyethylene glycol monomethyl ether methacrylate, 4-hydroxybutyl methacrylate, and allyl glycol carbonate.

[0032] In order to ensure the anti-ultraviolet performance of the photocurable material, the present invention preferably selects at least one of the ultraviolet absorber selected from 2-(2-hydroxy-3-allyl-5-methylphenyl)-2H-benzotriazole, 2-(2-hydroxy-5-methylphenyl)benzotriazole, 2-hydroxy-4-acryloyloxyethoxybenzotriazole, 2-hydroxy-4-alkoxybenzophenone and substituted acrylonitrile.

[0033] In the present invention, the photoinitiator is preferably selected from at least one of 184, 1173, TPO, TPO-L, 819, 2959, and LAP.

[0034] The photocurable material provided by the present invention is a biocompatible polymer that absorbs ultraviolet light, which is a copolymerization product of a mixture of polymerizable poly-β-serine and hydrophobic / hydrophilic acrylic and / or allele monomers, wherein the hydrophobic monomer includes at least one hydrophobic acrylic or allele monomer that absorbs ultraviolet light. The material can be used to produce deformable lenses, such as intraocular lenses, refractive intraocular contact lenses, and standard contact lenses, such as contact lenses for correcting aopia, myopia, and hyperopia.

[0035] Another object of the present invention is to provide a method for preparing the above-mentioned photocurable material, the method comprising the following steps: mixing a hydrophilic monomer, a hydrophobic monomer, a UV absorber, and a polymerizable poly-β-serine according to the formula amount, adding a photoinitiator, and irradiating the polymer with UV light, preferably at a power of 50 mW / m 2 The ultraviolet light was irradiated for 300 s to obtain a light-cured material.

[0036] The preparation method of the photocurable material provided in the present disclosure has a simple preparation process; by introducing polymerizable poly-β-serine into the raw materials, the prepared photocurable material can effectively reduce protein adsorption and microbial adhesion when used in contact lenses, thereby improving the anti-precipitate adsorption performance of the contact lenses while improving their antibacterial properties, which helps to extend the service life of the contact lenses.

[0037] Another object of the present invention is to provide a contact lens, which is prepared by the photocurable material as described above.

[0038] The contact lenses of the present invention include conventional contact lenses and phakic posterior chamber intraocular lenses.

[0039] The contact lens provided by the present invention is prepared by a photocurable material; the adopted photocurable material, by introducing polymerizable poly-β-serine into the raw material, can effectively reduce protein adsorption and microbial adhesion when used in the contact lens, thereby improving the anti-precipitate adsorption performance of the contact lens while improving its antibacterial property, which helps to extend the service life of the contact lens.

[0040] In order to make the above-mentioned objects, features and advantages of the present invention more obvious and easy to understand, specific embodiments of the present invention are described in detail below.

[0041] The photocurable materials in the embodiments and comparative examples of the present invention are prepared according to the following method: According to the formula, the hydrophilic monomer, the hydrophobic monomer, the ultraviolet absorber, and the polymerizable poly-β-serine are mixed, and a photoinitiator is added, and the polymerization is carried out by ultraviolet irradiation, preferably at 50 mW / m 2 The ultraviolet light was irradiated for 300 s to obtain a light-cured material.

[0042] Example 1 This embodiment provides a photocurable material, and the raw materials include the following components in parts by weight: 3 parts of polymerizable poly-β-serine; HMBP 30 servings; HEMA 60 parts; 6 parts of ultraviolet absorber 2-(2-hydroxy-3-allyl-5-methylphenyl)-2H-benzotriazole; Photoinitiator 184 1 part.

[0043] The polymerizable poly-β-serine is prepared as follows: S1: Preparation of acrylic acid-modified poly-β-serine using poly-β-serine and acryloyl chloride as raw materials: S11: A magnetic stirring bar was placed in a two-necked flat-bottomed flask, and poly-β-serine (1.75 g, about 0.25 mmol), TEA (0.27 mL, 2.02 mmol), and anhydrous THF (25 mL) were added to the two-necked flat-bottomed flask and mixed to obtain a first solution; S12: Add acryloyl chloride (0.16 mL, 2.02 mmol) to anhydrous THF (25 mL) and mix to obtain a second solution; S13: at 0° C. and under a nitrogen atmosphere, dropwise adding the second solution into the first solution, and reflux reacting, preferably reflux reacting for 24 hours, to obtain a reaction solution; S14: slowly adding the reaction solution into ethanol, filtering, precipitating, and washing, preferably washing with ethanol three times, to obtain acrylic acid-modified poly-β-serine; S2: dissolving acrylic acid-modified poly-β-serine in dimethyl sulfoxide (DMSO) (the mass concentration of acrylic acid-modified poly-β-serine after dissolution is 8%), slowly adding n-butylamine (2.02 mmol) dropwise, stirring and reacting at 60° C., preferably stirring and reacting for 12 h, until the double bonds are completely reacted, to obtain a first reaction solution; S3: Add 2-bromoethyl acrylate (2.02 mmol) to the first reaction solution, stir at 50° C. overnight, and after the reaction is completed, obtain a second reaction solution; S4: slowly adding the second reaction solution into diethyl ether, filtering, precipitating, and washing, preferably washing with diethyl ether three times, to obtain polymerizable poly-β-serine.

[0044] Example 2 The difference between this embodiment and embodiment 1 is that the polymerizable poly-β-serine is prepared according to the following method: S1: Preparation of acrylic acid-modified poly-β-serine using poly-β-serine and acryloyl chloride as raw materials: S11: A magnetic stirring bar was placed in a two-necked flat-bottomed flask, and poly-β-serine (1.75 g, about 0.25 mmol), TEA (0.2 mL, 1.5 mmol), and anhydrous THF (25 mL) were added to the two-necked flat-bottomed flask and mixed to obtain a first solution; S12: Add acryloyl chloride (0.12 mL, 1.5 mmol) to anhydrous THF (20 mL) and mix to obtain a second solution; S13: at 0° C. and under a nitrogen atmosphere, dropwise adding the second solution into the first solution, and reflux reacting, preferably reflux reacting for 24 hours, to obtain a reaction solution; S14: slowly adding the reaction solution into ethanol, filtering, precipitating, and washing, preferably washing with ethanol three times, to obtain acrylic acid-modified poly-β-serine; S2: dissolving acrylic acid-modified poly-β-serine in dimethyl sulfoxide (DMSO) (the mass concentration of acrylic acid-modified poly-β-serine after dissolution is 8%), slowly adding n-butylamine (1.5 mmol) dropwise, stirring and reacting at 60° C., preferably stirring and reacting for 12 h, until the double bonds are completely reacted, to obtain a first reaction solution; S3: Add 2-bromoethyl acrylate (1.5 mmol) to the first reaction solution, stir at 50° C. overnight, and after the reaction is completed, obtain a second reaction solution; S4: slowly adding the second reaction solution into diethyl ether, filtering, precipitating, and washing, preferably washing with diethyl ether three times, to obtain polymerizable poly-β-serine.

[0045] Example 3 The difference between this embodiment and embodiment 1 is that the polymerizable poly-β-serine is prepared according to the following method: S1: Preparation of acrylic acid-modified poly-β-serine using poly-β-serine and acryloyl chloride as raw materials: S11: A magnetic stirring bar was placed in a two-necked flat-bottomed flask, and poly-β-serine (1.75 g, about 0.25 mmol), TEA (0.34 mL, 2.5 mmol), and anhydrous THF (25 mL) were added to the two-necked flat-bottomed flask and mixed to obtain a first solution; S12: Add acryloyl chloride (0.2 mL, 2.5 mmol) to anhydrous THF (30 mL) and mix to obtain a second solution; S13: at 0° C. and under a nitrogen atmosphere, dropwise adding the second solution into the first solution, and reflux reacting, preferably reflux reacting for 24 hours, to obtain a reaction solution; S14: slowly adding the reaction solution into ethanol, filtering, precipitating, and washing, preferably washing with ethanol three times, to obtain acrylic acid-modified poly-β-serine; S2: dissolving acrylic acid-modified poly-β-serine in dimethyl sulfoxide (DMSO) (the mass concentration of acrylic acid-modified poly-β-serine after dissolution is 8%), slowly adding n-butylamine (2.5 mmol) dropwise, stirring and reacting at 60° C., preferably stirring and reacting for 12 h, until the double bonds are completely reacted, to obtain a first reaction solution; S3: Add 2-bromoethyl acrylate (2.5 mmol) to the first reaction solution, stir at 50° C. overnight, and after the reaction is completed, obtain a second reaction solution; S4: slowly adding the second reaction solution into diethyl ether, filtering, precipitating, and washing, preferably washing with diethyl ether three times, to obtain polymerizable poly-β-serine.

[0046] Example 4 The difference between this embodiment and embodiment 1 is that, in parts by weight, the raw materials include the following components: 5 parts of polymerizable poly-β-serine; EBA 30 copies; HEMA 60 parts; 4.9 parts of ultraviolet absorber 2-(2-hydroxy-3-allyl-5-methylphenyl)-2H-benzotriazole; Photoinitiator 184 0.1 parts.

[0047] Example 5 The difference between this embodiment and embodiment 1 is that, in parts by weight, the raw materials include the following components: 0.5 parts of polymerizable poly-β-serine; 10 parts of 3-allyl-4-hydroxyacetophenone; HEMA 80 parts; 6.5 parts of ultraviolet absorber 2-(2-hydroxy-3-allyl-5-methylphenyl)-2H-benzotriazole; Photoinitiator 184 3 parts.

[0048] Example 6 The difference between this embodiment and embodiment 1 is that, in parts by weight, the raw materials include the following components: 2 parts of polymerizable poly-β-serine; MMA 30 parts; HPMA 60 parts; 7 parts of ultraviolet absorber 2-(2-hydroxy-3-allyl-5-methylphenyl)-2H-benzotriazole; Photoinitiator 184 1 part.

[0049] Comparative Example 1 This comparative example provides a photocurable material, and the raw materials include the following components in parts by weight: HMBP 30 servings; HEMA 60 parts; 7 parts of ultraviolet absorber 2-(2-hydroxy-3-allyl-5-methylphenyl)-2H-benzotriazole; Photoinitiator 184 3 parts.

[0050] Comparative Example 2 This comparative example provides a photocurable material, and the raw materials include the following components in parts by weight: 3 parts of polymerizable poly-β-serine; HEMA 90 parts; 6 parts of ultraviolet absorber 2-(2-hydroxy-3-allyl-5-methylphenyl)-2H-benzotriazole; Photoinitiator 184 1 part.

[0051] Comparative Example 3 This comparative example provides a photocurable material, and the raw materials include the following components in parts by weight: 3 parts of polymerizable poly-β-serine; HMBP 90 parts; 6 parts of ultraviolet absorber 2-(2-hydroxy-3-allyl-5-methylphenyl)-2H-benzotriazole; Photoinitiator 184 1 part.

[0052] Comparative Example 4 The difference between this comparative example and Example 1 is that the acrylic acid-modified poly-β-serine prepared in Example 1 is used to replace the polymerizable poly-β-serine.

[0053] The performance of the photocurable materials prepared in the above embodiments and comparative examples was tested as follows: 1) Ultraviolet visible light transmittance: tested with UV-visible light spectrometer; 2) Elongation at break: tested by uniaxial tensile testing machine; 3) Anti-protein adhesion performance: Bovine fibrinogen (1 mg / mL, PBS, pH 7.4) and 100% fetal bovine serum (FBS) were used. The samples were placed in protein solution or 100% FBS (both for 3 h, 37°C, 5% CO2, 95% relative humidity). After protein adsorption, they were washed three times with PBS. Then, 1 ml of sodium dodecyl sulfate (SDS) solution (2 wt . %) was added for 30 minutes (37°C) to remove the adsorbed proteins on these samples. The amount of eluted protein in the SDS solution was quantified at 578 nm using the BCA protein assay kit; 4) Antibacterial performance: Cut several circular specimens of uniform shape and thickness from the sample and spread them flat in a 24-well plate. Take 0.1 mL of a 1×10 8 ~3×10 8 CFU / mL of Staphylococcus aureus liquid (PBS buffer) was inoculated on each sample. Each sample was divided into two groups and cultured in a light and dark room environment for 30 minutes, respectively. Then 0.9mL of PBS buffer was added to the corresponding 24-well plate containing the sample, and after mixing evenly, the original bacterial liquid and the bacterial liquid on the sample were diluted in a centrifuge tube in a gradient of 10 6 10-fold dilution series was prepared. 10 μ The L solution was injected onto a plate containing agar medium and placed in a constant temperature incubator at 37°C for 24 hours. Finally, the colony count was determined, the bacterial survival rate was calculated, and the antibacterial effect was evaluated.

[0054] The test results are shown in Table 1: Table 1 370nm UV light transmittance (%) 500nm visible light transmittance (%) Elongation at break (%) Protein adhesion performance (ug / cm2) Bacterial survival rate (%) Example 1 2.8 98.7 150 0.25 1.6 Example 2 3.6 99 208 0.26 1.7 Example 3 4.1 98.5 96 0.28 1.8 Example 4 3.2 99.2 152 0.12 1.0 Example 5 3.5 98.2 148 0.34 2.3 Example 6 3.8 98.8 151 0.28 2.2 Comparative Example 1 7.4 95.2 246 1.25 93.5 Comparative Example 2 8.3 94.3 139 1.28 4.3 Comparative Example 3 8.8 94.6 147 1.36 4.8 Comparative Example 4 7.2 95.1 56 1.17 92.3 It can be seen from the data in Table 1 that the photocurable materials prepared in various embodiments of the present invention have excellent optical and mechanical properties, as well as excellent anti-protein adhesion and antibacterial properties.

[0055] Compared with Example 1, the technical solution provided in Comparative Example 1 does not add polymerizable poly-β-serine, and the anti-cell adhesion and antibacterial properties of the prepared photocurable material are greatly reduced, and the strength is deteriorated.

[0056] Compared with Example 1, the technical solution provided in Comparative Example 2 does not add a hydrophobic monomer, and the prepared photocurable material has reduced cell adhesion resistance.

[0057] Compared with Example 1, the technical solution provided in Comparative Example 3 does not add hydrophilic monomers, and the prepared photocurable material has reduced cell adhesion resistance.

[0058] Compared with Example 1, the technical solution provided in Comparative Example 4 uses acrylic acid-modified poly-β-serine to replace the polymerizable poly-β-serine, and the elongation at break of the prepared photocurable material is reduced, and the antibacterial property is reduced.

[0059] Based on the above ideal embodiments of the present invention, the relevant staff can make various changes and modifications without departing from the technical concept of the present invention through the above description. The technical scope of the present invention is not limited to the contents of the specification, and its technical scope must be determined according to the scope of the claims.

Claims

1. A photocurable material, characterized in that: The raw materials include the following components in parts by weight: 0.1-5 parts of polymerizable poly-β-serine; 10-30 parts of hydrophobic monomer; 60-80 parts of hydrophilic monomer; 1-7 parts of ultraviolet absorber; Photoinitiator 0.1-3 parts.

2. The photocurable material according to claim 1, wherein: The polymerizable poly-β-serine is prepared according to the following method: S1: preparing acrylic acid-modified poly-β-serine using poly-β-serine and acryloyl chloride as raw materials; S2: dissolving the acrylic acid-modified poly-β-serine in dimethyl sulfoxide, adding n-butylamine dropwise, and reacting at 60° C. to obtain a first reaction solution; S3: adding 2-bromoethyl acrylate to the first reaction solution, reacting at 50° C. to obtain a second reaction solution; S4: adding the second reaction solution into diethyl ether, filtering, precipitating, and washing to obtain polymerizable poly-β-serine.

3. The photocurable material according to claim 2, wherein: The molar ratio of the poly-β-serine, the acryloyl chloride, the n-butylamine and the 2-bromoethyl acrylate is 1:(6-10):(6-10):(6-10).

4. The photocurable material according to claim 2, wherein: The method for preparing acrylic acid-modified poly-β-serine using poly-β-serine and acryloyl chloride as raw materials comprises: S11: mixing poly-β-serine, triethylamine and anhydrous tetrahydrofuran to obtain a first solution; S12: mixing acryloyl chloride and anhydrous tetrahydrofuran to obtain a second solution; S13: at 0° C. and in an inert gas atmosphere, dropping the second solution into the first solution, and reflux reaction to obtain a reaction solution; S14: adding the reaction solution into ethanol, filtering, precipitating, and washing to obtain acrylic acid-modified poly-β-serine.

5. The photocurable material according to any one of claims 1 to 4, characterized in that: The hydrophobic monomer is selected from at least one of 2-hydroxy-4-(methacryloyloxy)benzophenone, ethyl 3-benzoylacrylate, 3-allyl-4-hydroxyacetophenone, 2-(2-hydroxy-3-allyl-5-methylphenyl)-2H-benzotriazole, n-propyl methacrylate, allylbenzene, allyl butyrate, allyl anisole, ethyl methacrylate, methyl methacrylate, and n-heptyl methacrylate.

6. The photocurable material according to any one of claims 1 to 4, characterized in that: The hydrophilic monomer is selected from at least one of 2-hydroxyethyl methacrylate, hydroxypropyl methacrylate, allyl alcohol, polyethylene glycol monomethyl ether methacrylate, 4-hydroxybutyl methacrylate, and allyl glycol carbonate.

7. The photocurable material according to any one of claims 1 to 4, characterized in that: The ultraviolet absorber is selected from at least one of 2-(2-hydroxy-3-allyl-5-methylphenyl)-2H-benzotriazole, 2-(2-hydroxy-5-methylphenyl)benzotriazole, 2-hydroxy-4-acryloyloxyethoxybenzotriazole, 2-hydroxy-4-alkoxybenzophenone and substituted acrylonitrile.

8. The photocurable material according to any one of claims 1 to 4, characterized in that: The photoinitiator is selected from at least one of 184, 1173, TPO, TPO-L, 819, 2959 and LAP.

9. A method for preparing a photocurable material according to any one of claims 1 to 8, characterized in that: The method comprises the following steps: mixing a hydrophilic monomer, a hydrophobic monomer, an ultraviolet absorber and polymerizable poly-β-serine according to the formula amount, adding a photoinitiator, and polymerizing by ultraviolet light to obtain a photocurable material.

10. A contact lens, characterized in that: The method is prepared by using the photocurable material as described in any one of claims 1 to 8.

11. The contact lens according to claim 10, wherein: Including phakic posterior chamber intraocular lenses.