Silicone hydrogel contact lens material and preparation method and application thereof
By using L-arginine zwitterionic derivative monomers in contact lens materials, the slow and slow release of NO is achieved, solving the problem of ineffective reduction of eye inflammation and nutritional visual nerves in the prior art, and improving wear comfort and biocompatibility.
Patent Information
- Application Number
- CN202210898544.9
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2022-07-28
- Publication Date
- 2025-03-21
- Estimated Expiration
- 2042-07-28
AI Technical Summary
Existing contact lens materials cannot effectively and slowly release nitric oxide (NO), resulting in the inability to effectively reduce eye inflammation and nourish visual nerves, and the wearing comfort is also low.
Silica hydrogel contact lens material containing L-arginine zwitterionic derivative monomer is used to make the compound more stable and not easily elute, achieving slow slow release of NO through specific double bonds. When inflammation occurs in the eyes, the material can intelligently respond to release NO, lower ROS, and reduce inflammation.
It achieves a slow and slow release of NO, reduces eye inflammation, nourishes visual nerves, improves wear comfort, and maintains the biocompatibility and therapeutic effect of the material.
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Figure CN115353583B_ABST
Abstract
Description
Technical Field
[0001] The invention belongs to the technical field of biomedical materials, and in particular relates to a silicone hydrogel contact lens material and a preparation method and application thereof. Background Art
[0002] Contact lenses, also known as corneal contact lenses, are lenses worn on the cornea of the eyeball to correct vision or protect the eyes. According to the hardness of the material, they can be divided into two categories: hard contact lenses and soft contact lenses. Compared with hard contact lenses, soft contact lenses are more comfortable to wear. The original contact lens hydrogel material is polymerized by hydrophilic monomers such as hydroxyethyl methacrylate. This type of contact lens has low water content and poor oxygen permeability. It has a strong foreign body sensation when worn and can also cause a series of corneal diseases. After that, various other monomers began to be added to the hydrophilic monomer to improve its performance, so that the water content, oxygen permeability and comfort of the material have also been improved. In daily work and life, the eyes are very susceptible to fatigue. When the eyes are overused and the eyes are tired, the eye sockets will feel uncomfortable and painful, the eyebrows will be sore, and symptoms such as fear of light and tears will appear, which will affect the patient's optic nerve and retina, and the intraocular pressure will increase pathologically, resulting in partial damage to the visual field and unclear vision, which will cause a series of eye diseases.
[0003] The cornea is located at the front of the eyeball and is in direct contact with the outside world. It is easily damaged and inflamed. Inflammatory reactions of the cornea caused by various factors are collectively referred to as keratitis, which is one of the common ophthalmic diseases and one of the main causes of blindness in my country. Corneal foreign bodies, corneal abrasions, improper use of corneal contact lenses, eye contact with contaminated drugs or water sources, etc. are common susceptibility factors for infectious keratitis. Patients with diabetes, malnutrition, and chronic wasting diseases are also susceptible to keratitis due to decreased resistance. Keratitis is clinically manifested by irritating symptoms such as blurred vision, pain, photophobia, and tearing, as well as obvious vision loss. In severe cases, corneal perforation, intraocular infection, and even blindness may occur.
[0004] Nitric oxide (NO) is an endogenous gas signaling molecule that plays a relevant role in the eye as a neuromodulator and vasodilator. NO promotes aqueous humor outflow by activating the soluble guanylate cyclase (sGC)-cyclic guanosine monophosphate (cGMP) pathway and directly reduces aqueous humor formation through the regulation of ion transporters, thereby reducing intraocular pressure. In addition, NO can maintain the basic blood flow of ocular tissues, regulate the tension of retinal blood vessels, and promote vascular relaxation.
[0005] In the prior art, CN 112159505 A discloses a medium water content, high oxygen permeability silicone hydrogel and silicone hydrogel contact lens, wherein the silicone monomer contains 10-60%, hydrophilic monomer 10-60%, cross-linking agent 0.1-10%, initiator 0.1-10%, solvent 30-60%. The silicone hydrogel provided by the patent has a medium water content and a large oxygen permeability coefficient. The contact lens made of the silicone hydrogel has high transparency, good oxygen permeability, and soft lenses, taking into account the requirements of wearing comfort and formability of contact lenses, but cannot produce and release NO. In the prior art, arginine monomer usually releases NO, but if arginine monomer is directly added to the raw material, the arginine monomer is easily eluted and cannot play a role. Therefore, it is very important to develop a contact lens material that can effectively control the release of NO from arginine monomer. Summary of the invention
[0006] Purpose of the invention: In view of the problems existing in the prior art, the present invention provides a silicone hydrogel contact lens material that can slowly release nitric oxide, effectively reduce eye inflammation, nourish the optic nerve, and has high wearing comfort. The present invention not only has excellent biocompatibility and meets the needs of daily wear, but also can intelligently respond to release NO when the eye is inflamed through a specific combination, thereby achieving the effect of anti-inflammatory and nourishing the optic nerve. The so-called intelligent response means that if the eye is inflamed, the silicone hydrogel contact lens containing the zwitterionic derivative of L-arginine can react with the inflammatory factor; if the eye is not inflamed, the above reaction does not occur.
[0007] The invention also provides a preparation method and application of the silicone hydrogel contact lens material.
[0008] Technical solution: In order to achieve the above-mentioned purpose, the present invention provides a silicone hydrogel contact lens material, comprising the following raw materials in parts by weight: 0.2-0.8 parts of L-arginine zwitterionic derivative monomer, 40-80 parts of hydrophilic monomer, 20-40 parts of siloxane monomer, 0.5-2 parts of initiator, and 0.5-2 parts of crosslinking agent.
[0009] Wherein, the L-arginine zwitterionic derivative is a reactive oxygen species (ROS) responsive type.
[0010] Wherein, the L-arginine zwitterionic derivative monomer is a compound having a high-density active guanidine functional group.
[0011] The L-arginine zwitterionic derivative monomer is a compound having a high-density active guanidine functional group and a carbon-carbon double bond at the chain end.
[0012] Preferably, the monomer structure of the L-arginine zwitterionic derivative is as follows:
[0013]
[0014] Wherein, the initiator is any one of an azo initiator, 2-hydroxy-2-methyl-1-phenylpropanone, and benzophenone.
[0015] Preferably, the initiator is 2-hydroxy-2-methyl-1-phenylpropanone.
[0016] Furthermore, the cross-linking agent is any one of ethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, and N,N-methylenebisacrylamide.
[0017] Preferably, the cross-linking agent is N,N-methylenebisacrylamide.
[0018] Wherein, the hydrophilic monomer is one or more of polyvinyl alcohol, methyl methacrylate, hydroxyethyl methacrylate, and N-vinyl pyrrolidone, preferably hydroxyethyl methacrylate and N-vinyl pyrrolidone.
[0019] Wherein, the siloxane monomer is one or more silane coupling agents containing Si-O-Si bonds, preferably 3-methacryloxypropyltrimethoxysilane.
[0020] The method for preparing the silicone hydrogel contact lens material of the present invention comprises the following steps:
[0021] (1) preparing an L-arginine zwitterionic derivative monomer: dissolving L-arginine powder in a mixed solvent of deionized water and 1,4-dioxane, adding triethylamine, and dropping methacrylic anhydride to react with stirring to obtain an L-arginine zwitterionic derivative;
[0022] (2) Mixing L-arginine zwitterionic derivative monomers with hydrophilic monomers and siloxane monomers, adding initiators and crosslinking agents, stirring at room temperature, injecting into a mold, irradiating with ultraviolet light, and then demolding and soaking to obtain a silicone hydrogel contact lens.
[0023] Furthermore, in the step (2), the mass ratio of the hydrophilic monomer to the siloxane monomer is 2-4:1-2.
[0024] Furthermore, the ultraviolet light irradiation time in step (2) is 4-9 minutes.
[0025] Preferably, the ultraviolet light irradiation time in step (2) is 7 minutes.
[0026] Preferably, the L-arginine zwitterionic derivative monomer is prepared by dissolving L-arginine in a mixed solvent of deionized water and 1,4-dioxane, dispersing by ultrasonication, stirring magnetically at room temperature, adding triethylamine, and cooling the solution to 0°C with an ice-water bath. After adding methacrylic anhydride dropwise under magnetic stirring, the ice-water bath is removed, and the reaction is continued by stirring at room temperature to obtain the L-arginine zwitterionic derivative.
[0027] Preferably, the L-arginine solution is 11.5 mmol.
[0028] Preferably, the 1,4-dioxane solution is 8.5 mL.
[0029] Preferably, the triethylamine is 4.5 mL.
[0030] Preferably, the reaction time is 12 h.
[0031] The silicone hydrogel contact lens material of the present invention is used in biomedical fields such as eliminating eye inflammation and nourishing optic nerves.
[0032] The silicone hydrogel contact lens material of the present invention is used in preparing contact lenses for eliminating eye inflammation and nourishing optic nerves.
[0033] The present invention proposes for the first time a contact lens material with intelligent response and sustained release of NO, which can react with the reactive oxygen species generated in the microenvironment of the eye inflammation site to continuously release NO, reduce ROS, and alleviate eye inflammation. The present invention chemically bonds arginine derivatives to the contact lens substrate, and finds that specific double bond bonding (covalent bonding of the double bonds on L-arginine to the double bonds in the contact lens substrate) is crucial for drug (NO) sustained release. The present invention initiates double bond polymerization of specific L-arginine zwitterionic derivative monomers with hydrophilic monomers and siloxane monomers under ultraviolet light irradiation. Unlike simple L-arginine small molecules, this method of covalent bonding using chemical bonds makes the compound more stable and not easy to be eluted, which is conducive to the slow release of NO and maintains the therapeutic effect of the material during wearing. In addition, low concentrations of NO promote cell proliferation, and high concentrations of NO kill cells. Therefore, the amount of monomeric L-arginine zwitterionic derivatives added in the present invention is also the key to controlling the amount of NO sustained release. The L-arginine derivative monomer used in the present invention not only retains the original dense guanidine active sites of arginine, enabling it to respond to reactive oxygen in the inflammatory microenvironment, and can continuously produce NO compared to small molecule NO donors; it also innovatively covalently bonds with the contact lens substrate through the newly assigned double bonds, and is applied to the ocular inflammatory microenvironment.
[0034] Beneficial effects: Compared with the prior art, the present invention has the following advantages:
[0035] 1. The material monomer L-arginine zwitterion derivative used in the present invention has dense guanidine active sites. Combining it with the contact lens material can not only meet the needs of daily wear, but also intelligently respond to the reactive oxygen generated in the microenvironment of the inflammatory site to continuously release NO, reduce ROS, and alleviate eye inflammation if the eye is inflamed.
[0036] 2. The preparation method of the present invention is simple and efficient, and the synthesis conditions are mild. The L-arginine zwitterionic derivative monomer, the hydrophilic monomer, and the siloxane monomer initiate double bond polymerization under ultraviolet light irradiation. Different from the simple L-arginine small molecule, this method of covalent bonding by chemical bonds makes the compound more stable and not easy to be eluted, which is beneficial to the slow release of NO and maintains the therapeutic effect of the material during wearing.
[0037] 3. The silicone hydrogel contact lens material prepared by the present invention has excellent biocompatibility, and its sustained release of NO can reduce intraocular pressure and nourish the optic nerve, and can be used in the preparation of contact lenses for eliminating eye inflammation and nourishing the optic nerve. BRIEF DESCRIPTION OF THE DRAWINGS
[0038] Figure 1 is the mass spectrum of the derivative of L-arginine in Example 1;
[0039] Figure 2 is the guanidine content of the L-arginine zwitterionic derivative detected in Example 2;
[0040] Figure 3 is the infrared spectra of Examples 3 and 4;
[0041] Figure 4 The silicone hydrogel contact lens material having anti-inflammatory effect and optic nerve nutrition prepared in Examples 3 and 4;
[0042] Figure 5 The sustained release of NO from the silicone hydrogel contact lens material having anti-inflammatory effects and nourishing the optic nerve in Example 6;
[0043] Figure 6 The biocompatibility evaluation of Example 7;
[0044] Figure 7 This is an evaluation of the anti-inflammatory and nutritional visual nerve performance of Example 8. DETAILED DESCRIPTION
[0045] The technical solution of the present invention is further described in detail below in conjunction with the accompanying drawings and embodiments.
[0046] The experimental methods described in the examples are conventional methods unless otherwise specified; the reagents and materials described are commercially available unless otherwise specified.
[0047] Example 1
[0048] Preparation of L-arginine zwitterionic derivative monomers
[0049] 2 g of L-arginine powder was dissolved in a mixed solvent of deionized water (11.5 mmol) and 1,4-dioxane (8.5 mL), ultrasonically dispersed, triethylamine (4.5 mL) was added, and the solution was cooled to 0°C with an ice-water bath. Methacrylic anhydride (3 mL) was added dropwise under magnetic stirring, and the ice-water bath was removed. The reaction was continued at room temperature with stirring for 12 h. The above solution was added dropwise to 400 mL of acetone for precipitation, and then the precipitate was redissolved in water and precipitated again in acetone. The precipitation step was repeated twice and dissolved in water; the solution was centrifuged at 8000 rpm for 15 min, the upper liquid was discarded, the lower precipitate was taken, and vacuum dried at 60°C to obtain L-arginine derivative monomer powder for subsequent examples.
[0050] The monomer structure of the L-arginine zwitterionic derivative is as follows:
[0051]
[0052] like Figure 1 The mass spectrum of the L-arginine zwitterionic derivative shown is [m / z] = 243.2 (M+H + ) , M(C 10 H 18 N4O3)=242.27, indicating the successful synthesis of the L-arginine zwitterionic derivative monomer.
[0053] Example 2
[0054] Detection of Guanidine Content in L-Arginine Derivatives
[0055] The guanidine content in the L-arginine derivative monomer was detected by colorimetric method: 1 mL of naphthol-diacetyl colorimetric solution and different series of concentrations of L-arginine standard solutions (1 μg / mL, 5 μg / mL, 10 μg / mL, 20 μg / mL, 50 μg / mL, 100 μg / mL, 200 μg / mL, 250 μg / mL, 500 μg / mL, 1000 μg / mL) were prepared. 100 μL of arginine standard solutions or L-arginine derivative monomers (100 μg mg -1 ) were added to the above 1 mL naphthol-diacetyl chromogenic solution for 15 minutes. The absorbance of the solution was measured at 570 nm. Figure 2 As shown, the content of guanidine groups in the L-arginine zwitterionic derivative monomer was measured to be 7.18 μmoL / mg.
[0056] Example 3
[0057] Preparation of silicone hydrogel contact lens materials
[0058] According to weight, 0.25 parts of L-arginine derivative monomer aqueous solution (30 mg / mL) were mixed evenly with 40 parts of hydrophilic monomer hydroxyethyl methacrylate, 40 parts of N-vinyl pyrrolidone, and 20 parts of siloxane monomer 3-(methacryloyloxy)propyl trimethoxysilane, and then 1 part of photoinitiator 2-hydroxy-2-methyl-1-phenylacetone and 0.8 parts of cross-linking agent N, N-methylenebisacrylamide were added and mixed evenly, stirred at room temperature for 2 hours, injected into the mold, and irradiated with ultraviolet light (36w, wavelength 365nm) for 7 minutes to initiate polymerization, and demolded after cooling to room temperature. After washing with water and extracting with ethanol to remove unreacted monomers or oligomers, the silicone hydrogel contact lens material was obtained by immersing in physiological saline.
[0059] Example 4
[0060] According to weight, 0.5 parts of L-arginine derivative monomer aqueous solution (30 mg / mL) was mixed with 40 parts of hydrophilic monomer hydroxyethyl methacrylate, 40 parts of N-vinyl pyrrolidone, and 20 parts of siloxane monomer 3-(methacryloyloxy)propyl trimethoxysilane, and then 1 part of photoinitiator 2-hydroxy-2-methyl-1-phenylacetone and 0.8 parts of cross-linking agent N, N-methylenebisacrylamide were added and mixed evenly, stirred at room temperature for 2 hours, injected into the mold, and irradiated with ultraviolet light (36w, wavelength 365nm) for 7 minutes to initiate polymerization, and demolded after cooling to room temperature. After washing with water and extracting with ethanol to remove unreacted monomers or oligomers, the silicone hydrogel contact lens material was obtained by immersing in physiological saline.
[0061] like Figure 3 As shown, silicone hydrogel contact lens materials are between 1750 and 1650 cm -1 The peaks at 3400-2500 cm-1 may be attributed to the stretching vibration peak of C=O, the in-plane bending vibration peak of NH, and the C=N characteristic peak of guanidine. -1 There are stretching vibration peaks from carboxyl hydroxyl groups and 1100-1000 cm -1 The characteristic absorption peak of the group Si-O-Si at is confirmed. It is confirmed that the L-arginine zwitterionic derivative and the prepolymer (hydrophilic monomer and siloxane monomer) are polymerized to successfully prepare a silicone hydrogel contact lens material with anti-inflammatory effect and optic nerve nutrition. Figure 4 As shown, the silicone hydrogel contact lens materials prepared in Examples 3 and 4 have smooth surfaces, are colorless and transparent.
[0062] Comparative Example 1
[0063] The method of Example 4 is adopted, except that no L-arginine derivative monomer is added to obtain the silicone hydrogel contact lens material.
[0064] Comparative Example 2
[0065] The method of Example 4 is adopted, except that the L-arginine derivative monomer is replaced with L-arginine to obtain the silicone hydrogel contact lens material.
[0066] Example 5
[0067] Sustained release of NO from silicone hydrogel contact lens materials with anti-inflammatory effects and optic nerve nutrition
[0068] (1) 0.25 g of each of the silicone hydrogel contact lens materials of Examples 3 and 4 and Comparative Examples 1 and 2 were placed in a 24-well plate, and 500 μM 1.5 mL / well H2O2 solution was added.
[0069] (2) After the material was incubated with H2O2 solution for specific time points (0h, 2h, 4h, 6h, 8h, 10h, 12h, 24h), the NO release was detected using a NO detection kit (Biyuntian).
[0070] (3) Figure 5As shown, 500 μM H2O2 was used to simulate the ROS generated by the ocular inflammation environment. With the blank contact lens material group (Comparative Example 1) as the control, the material group with L-arginine added alone (Comparative Example 2) had no obvious NO release at the corresponding time point. This is because the addition of L-arginine is unstable and has been eluted in the water washing and organic extraction process of the contact lens preparation process; while the material group with L-arginine derivative monomer added (Examples 3 and 4) achieved a sustained and slow release of NO. It shows that compared with the simple addition of L-arginine, the silicone hydrogel contact lens material containing L-arginine derivative monomer produced by covalent bonding is more stable and not easy to elute. It can be seen from Examples 3 and 4 in the data graph that the more the proportion of L-arginine zwitterion derivative monomer is increased, the more NO is released, indicating that the addition amount of different L-arginine zwitterion derivative monomers has an important influence on the sustained release of NO from silicone hydrogel contact lens materials. However, NO has the property of promoting cell proliferation at low concentrations and killing cells at high concentrations. Therefore, it is necessary to reasonably regulate the amount of L-arginine zwitterion derivative monomer added to ensure that NO is not released too much. At the same time, considering the actual application of silicone hydrogel contact lens materials, too much L-arginine zwitterion derivative monomer added will also affect the transparency and other properties of the material itself. When the weight part of the aqueous solution of L-arginine derivative monomer in Example 4 of the present invention is 1 part, although NO can be continuously released, too much L-arginine derivative monomer solution affects the properties of the contact lens material itself, making it poor in light transmission performance, weak in mechanical properties, and fragile. Therefore, the weight part of the L-arginine derivative monomer solution in this embodiment should not exceed 0.8 parts.
[0071] Example 6
[0072] Biocompatibility evaluation of silicone hydrogel contact lenses with anti-inflammatory and optic nerve nutrition
[0073] (1) 0.04 g of each of the silicone hydrogel contact lens materials of Examples 3, 4 and Comparative Example 1 were sterilized and placed in 1 mL of cell culture medium (endothelial-specific culture medium: fetal bovine serum: dual antibody: endothelial growth factor = 93:5:1:1 (v / v)%) for leaching, and the leaching was carried out in a 37°C incubator for 24 h. The supernatant was taken as the original leaching solution.
[0074] (2) Human umbilical vein endothelial cells were cultured at 2*10 5cell / mL was inoculated in a 96-well plate. After the cells adhered to the wall, the original culture medium of the 96-well culture plate was discarded, leaving the cell layer. The series of leaching solutions obtained in step 1 above were added at 100 μL / well. The negative control group added the corresponding volume of fresh cell culture solution, and the positive control group added the corresponding volume of PBS solution. After the material leaching solution and cells were incubated for 24 hours, the cell activity was detected using MTT reagent, the absorbance values between the groups were compared, and the relative cell survival rate was calculated.
[0075] (3) Figure 6 As shown, compared with the negative control group (without contact lens material), there was no significant difference in the absorbance of the leaching solutions of different contact lens materials. The relative cell proliferation rate value was significantly different from that of the positive control group, but had the same change trend as the negative control group. It can be considered that the contact lens material has excellent biocompatibility.
[0076] Example 8
[0077] Evaluation of the anti-inflammatory and optic nerve nourishing properties of silicone hydrogel contact lens materials with anti-inflammatory and optic nerve nourishing effects
[0078] (1) Human corneal epithelial cells were cultured at 2*10 5 cell / mL were inoculated in a 24-well plate. After the cells adhered to the wall, the original culture medium was discarded, leaving the cell layer. The positive control group and the material group were respectively added with 500 μL / well of cell culture medium containing LPS (special culture medium for human corneal epithelial cells), wherein the concentration of LPS was 1 μg / mL. The negative control group was only added with the corresponding volume of cell culture medium, and incubated in a 37°C incubator for 24 hours to stimulate the cells to produce inflammation. The latter material group was respectively added with 0.04 g of the contact lens materials of Examples 3 and 4 and Comparative Example 1, and the incubation continued in a 37°C incubator for 24 hours. The cell activity was detected using MTT reagent, the absorbance values between the groups were compared, and the relative cell survival rate was calculated.
[0079] (3) Figure 7 As shown, compared with the positive control group, the relative cell proliferation rate values of the negative control group and the material group increased significantly. There was no significant difference between the simple contact lens material group (0+LPS, comparative example 1) and the negative control group (culture solution without LPS), while the relative cell proliferation rate of the composite contact lens material group showed an upward trend compared with the negative control group, indicating that the composite contact lens material is beneficial to eliminate inflammation and promote cell proliferation in the inflammatory environment stimulated by LPS.
[0080] Example 9
[0081] According to weight, 0.2 parts of L-arginine derivative monomer aqueous solution (30 mg / mL) was mixed with 20 parts of hydrophilic monomer methyl methacrylate, 20 parts of N-vinyl pyrrolidone, and 20 parts of siloxane monomer 3-(methacryloyloxy)propyl trimethoxysilane, and then 0.5 parts of photoinitiator benzophenone and 0.5 parts of cross-linking agent ethylene glycol dimethacrylate were added and mixed evenly, stirred at room temperature for 2 hours, injected into the mold, and irradiated with ultraviolet light (36w, wavelength 365nm) for 4 minutes to initiate polymerization, and demolded after cooling to room temperature. After washing with water and extracting with ethanol to remove unreacted monomers or oligomers, the silicone hydrogel contact lens material was obtained by immersing in physiological saline.
[0082] Example 10
[0083] According to weight, 0.8 parts of L-arginine derivative monomer aqueous solution (30 mg / mL) was mixed with 30 parts of hydrophilic monomer hydroxyethyl methacrylate, 30 parts of N-vinyl pyrrolidone, and 40 parts of siloxane monomer 3-(methacryloyloxy)propyl trimethoxysilane, and then 2 parts of photoinitiator 2-hydroxy-2-methyl-1-phenylacetone and 0.8 parts of cross-linking agent triethylene glycol dimethacrylate were added and mixed evenly, stirred at room temperature for 2 hours, injected into the mold, and irradiated with ultraviolet light (36w, wavelength 365nm) for 9 minutes to initiate polymerization, and demolded after cooling to room temperature. After washing with water and extracting with ethanol to remove unreacted monomers or oligomers, the silicone hydrogel contact lens material was obtained by immersing in physiological saline.
Claims
1. A silicone hydrogel contact lens material, characterized in that: The silicone hydrogel contact lens material comprises the following raw materials in parts by weight: 0.2-0.8 parts of L-arginine zwitterionic derivative monomer, 40-80 parts of hydrophilic monomer, 20-40 parts of siloxane monomer, 0.5-2 parts of initiator, and 0.5-2 parts of crosslinking agent; The monomer structure of L-arginine zwitterionic derivative is shown below: ; The hydrophilic monomer is hydroxyethyl methacrylate and N-vinyl pyrrolidone; the siloxane monomer is 3-(methacryloyloxy)propyltrimethoxysilane; The preparation method of the hydrogel contact lens material comprises the following steps: The L-arginine zwitterionic derivative monomer is mixed with a hydrophilic monomer and a siloxane monomer, and then an initiator and a cross-linking agent are added, stirred at room temperature, injected into a mold, irradiated with ultraviolet light, and then demolded and immersed to obtain a silicone hydrogel contact lens material; the mass ratio of the hydrophilic monomer to the siloxane monomer is 2~4:1~2.
2. The silicone hydrogel contact lens material according to claim 1, characterized in that: The initiator is any one of azo initiator, 2-hydroxy-2-methyl-1-phenylpropanone and benzophenone; the crosslinking agent is any one of ethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate and N,N-methylenebisacrylamide.
3. A method for preparing the silicone hydrogel contact lens material according to claim 1, characterized in that: The steps include: (1) Preparation of L-arginine zwitterionic derivative monomers: dissolving L-arginine powder in a mixed solvent of deionized water and 1,4-dioxane, adding triethylamine, and dropping methacrylic anhydride to react with stirring to obtain an L-arginine derivative; (2) Mixing L-arginine zwitterionic derivative monomers with hydrophilic monomers and siloxane monomers, adding initiators and crosslinking agents, stirring at room temperature, injecting into a mold, irradiating with ultraviolet light, and then demolding and soaking to obtain a silicone hydrogel contact lens material.
4. The method for preparing a silicone hydrogel contact lens material according to claim 3, characterized in that: In step (2), the mass ratio of the hydrophilic monomer to the siloxane monomer is 2-4:1-2; and the ultraviolet light irradiation time is 4-9 min.
5. Use of the silicone hydrogel contact lens material according to claim 1 in preparing contact lenses for eliminating eye inflammation and nourishing optic nerves.
Citation Information
Patent Citations
Silicon hydrogel with medium water content and high oxygen permeability and silicon hydrogel contact lenses
CN112159505A
Amino acid-based polymerizable compounds and ophthalmic devices prepared therefrom
CN114096514A