Preparation and application of flexible acrylate copolymer with high optical performance

The preparation of flexible acrylate copolymers with high optical properties through polymerization of high refractive acrylate monomers has solved the problem of insufficient light transmittance and refractive index of existing materials, and achieved a balance of high light transmittance, ultraviolet protection and mechanical properties. It is suitable for artificial lens materials for minimally invasive surgery.

CN120248198APending Publication Date: 2025-07-04XIAMEN UNIV
View PDF 2 Cites 0 Cited by

Patent Information

Application Number
CN202510594373.4
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2025-05-09
Publication Date
2025-07-04

AI Technical Summary

Technical Problem

The existing intraocular lens materials have shortcomings in light transmittance and refractive index, making it difficult to take into account high optical performance and flexibility, which affects surgical results and visual quality.

Method used

The polymerization of high refractive acrylate monomers was performed to prepare flexible acrylate copolymers with high optical properties. The copolymer material was obtained through two-stage heating polymerization and washing and drying processes.

Benefits of technology

The prepared copolymer material has a light transmittance of more than 90% in the visible light range and a refractive index of more than 1.55. It has ultraviolet protection function and a tensile strength of more than 3.5MPa. It meets the needs of minimally invasive surgery, balances mechanical properties and flexibility, and reduces production difficulty and cost.

✦ Generated by Eureka AI based on patent content.

Smart Images

  • Figure CN120248198A_ABST
    Figure CN120248198A_ABST
Patent Text Reader

Abstract

The invention discloses preparation and application of a flexible acrylate copolymer with high optical performance, and relates to the field of organic chemistry. The preparation method comprises the following steps: mixing a first monomer containing a benzene ring structure, a second monomer, a cross-linking agent and an initiator to obtain a mixed solution; degassing the mixed solution, adopting a two-stage thermal polymerization mode, and finally washing and drying to obtain a copolymer finished product. The glass transition temperature of the material is lower than 20 DEG C, the visible light transmittance exceeds 90%, the refractive index is larger than or equal to 1.55, the material has the ultraviolet protection function, and the tensile strength and the elongation meet the folding and implanting requirements of an artificial lens. By preparing the flexible acrylate copolymer with high optical performance, the copolymer has good flexibility, shows excellent optical performance compared with a common soft material, and is applied to preparation of intraocular lenses. The problems that an existing high-refractive-index material is insufficient in light transmittance, the flexibility and the optical performance are difficult to consider and the like are solved, and the visual quality and the surgical adaptability are remarkably improved.
Need to check novelty before this filing date? Find Prior Art

Description

Technical Field

[0001] The present invention relates to the field of organic chemistry, and particularly to the preparation and application of a flexible acrylate copolymer with high optical properties. Background Art

[0002] Cataract is a disease caused by metabolic disorders of the lens due to reasons such as aging, genetics, and radiation, resulting in the denaturation and turbidity of lens proteins. With the increasing aging of the population, the incidence of cataract is getting higher and higher. At the same time, cataract is the main cause of blindness globally. And surgical replacement of intraocular lenses (IOLs) is the only effective method for treating cataracts. With the continuous progress of medical science, current surgeries are increasingly trending towards minimally invasive procedures, which also requires the material to be thinner, further demanding an increase in the refractive index of the material. Chinese Patent CN106632826A discloses a foldable intraocular lens material and its preparation method, but its refractive index is 1.53, still having room for further improvement. Chinese Patent CN110003385A discloses a preparation method of an intraocular lens with a high refractive index. Although the refractive coefficient reaches above 1.55, the light transmittance of the material still needs to be further improved. Therefore, preparing an intraocular lens with high optical properties can provide patients with a better visual experience effect and improve visual quality. Summary of the Invention

[0003] The purpose of the present invention is to solve the above problems in the prior art, and provide the preparation and application of a flexible acrylate copolymer with high optical properties. By polymerizing acrylate monomers with a high refractive index, a flexible acrylate copolymer with high optical properties is prepared and applied to the material for preparing intraocular lenses.

[0004] To achieve the above purpose, the present invention adopts the following technical solutions:

[0005] A preparation method of a flexible acrylate copolymer with high optical properties, comprising the following steps:

[0006] 1) Put the first monomer, the second monomer, the crosslinking agent and the initiator in a beaker, mix and stir until the solution is clear to obtain a mixed solution;

[0007] 2) Carry out vacuum degassing on the mixed solution, inject the mixed solution into a mold, and put the mold into an oven for two-stage heating polymerization;

[0008] 3) After the reaction is completed, wait for the sample to cool to room temperature, disassemble the mold and take out the sample, wash the obtained sample successively with absolute ethanol and deionized water, and dry it to obtain the copolymer material.

[0009] In step 1), the first monomer includes at least one of phenethyl acrylate, phenylpropyl acrylate, phenethyl methacrylate, phenylpropyl methacrylate, phenylbutyl acrylate, and phenylbutyl methacrylate.

[0010] The second monomer includes at least one of phenyl ether acrylate, ethylene glycol phenyl ether acrylate, diphenyl ether methacrylate, ethylene glycol methacrylate, and ethylene glycol phenyl ether methacrylate;

[0011] In step 1), the weight ratio of the first monomer to the second monomer is (1:9) to (9:1); the addition amount of the crosslinking agent is 1% to 10% of the total weight of the first monomer and the second monomer, and the addition amount of the initiator is 0.1% to 5% of the total weight of the first monomer and the second monomer; the crosslinking agent is selected from at least one of 1,4-butanediol diacrylate, 1,4-butanediol dimethacrylate, and 1,6-hexanediol diacrylate; the initiator is a thermal initiator, and the initiator can be azobisisobutyronitrile.

[0012] In step 2), the degassing time is 1 to 10 h; the specific conditions for two-stage heating polymerization are that the temperature in the first stage is 50 to 100 °C and the reaction time is 2 to 20 h; the temperature in the second stage is 100 to 150 °C and the reaction time is 1 to 10 h.

[0013] The present invention provides a high-optical-performance flexible hydrophobic acrylate copolymer obtained by the above preparation method.

[0014] The present invention provides an application of a high-optical-performance flexible hydrophobic acrylate copolymer in the preparation of intraocular lens materials.

[0015] Compared with the prior art, the beneficial effects of the present invention are:

[0016] The present invention polymerizes acrylate monomers containing a benzene ring structure to prepare a high-optical-performance flexible acrylate copolymer. The prepared copolymer has a glass transition temperature lower than 20 °C, a light transmittance exceeding 90% in the visible light range, and a refractive index exceeding 1.55. It also has an ultraviolet protection function and can effectively block UV-C band radiation to protect the retina. The tensile strength is greater than 3.5 MPa, meeting the minimally invasive implantation requirements of foldable and easily deployable intraocular lenses, and achieving a balance between mechanical properties and flexibility; experiments prove that its optical, thermal, and mechanical properties all meet industry standards, the preparation process is simple, which is conducive to reducing production difficulty and cost, and the solution has strong repeatability. The material of the present invention is applied to the preparation of intraocular lenses, providing an efficient and reliable solution for high-performance intraocular lens materials, and improving the visual quality and surgical adaptability of patients. Description of the Drawings

[0017] Figure 1Transmittance measurement diagram of the copolymer material of Example 1.

[0018] Figure 2 Refractive index measurement diagram of the copolymer materials of Examples 1-6.

[0019] Figure 3 Mechanical property measurement diagram of the copolymer materials of Examples 1-6.

[0020] Figure 4 DSC measurement diagram of the copolymer material of Example 2. Detailed implementation manners

[0021] In order to make the technical problems, technical solutions and beneficial effects to be solved by the present invention clearer and more understandable, the present invention will be further described in detail below with reference to the accompanying drawings and embodiments.

[0022] Example 1

[0023] (1) 8.0 g of phenethyl acrylate, 8.0 g of ethylene glycol phenyl ether methacrylate, 0.32 g of 1,4-butanediol diacrylate, and 0.064 g of azobisisobutyronitrile were placed in a beaker, mixed and stirred for 1 h until the solution became clear to prepare a mixed solution;

[0024] (2) The mixed solution was put into a vacuum drying oven for degassing for 2 h, then injected into a mold, and then transferred to an oven at 60 °C for polymerization reaction for 5 h, and then put into an oven at 110 °C for polymerization reaction for 4 h;

[0025] (3) After the reaction was completed, the sample was cooled to room temperature, the mold was disassembled to take out the sample, and the obtained sample was washed successively with absolute ethanol and deionized water, 3 times each, 10 min each time; then the sample was put into a vacuum drying oven at 60 °C for vacuum drying for 24 h to obtain an acrylate copolymer material.

[0026] Figure 1 It is the transmittance measurement diagram of the copolymer material of Example 1. It can be analyzed from the figure that in the visible light range (800 - 400 nm), the transmittance of the copolymer material of Example 1 is greater than 95%. In addition, in the ultraviolet range (400 - 200 nm), its transmittance drops rapidly, and in the UV-C interval (280 - 200 nm), the transmittance of the material drops to 0, protecting the retina from ultraviolet radiation damage to a certain extent.

[0027] Example 2

[0028] (1) 0.20 g of phenethyl acrylate, 0.80 g of ethylene glycol phenyl ether methacrylate, 0.02 g of 1,4-butanediol diacrylate, and 0.004 g of azobisisobutyronitrile were placed in a beaker, mixed and stirred for 1 h until the solution became clear to prepare a mixed solution;

[0029] (2) Put the mixed solution into a vacuum drying oven for degassing for 2 h, then inject it into a mold, and then transfer it to an oven at 60 °C for polymerization reaction for 5 h, and then put it into an oven at 110 °C for polymerization reaction for 4 h;

[0030] (3) After the reaction is completed, wait for the sample to cool to room temperature, disassemble the mold and take out the sample. Wash the obtained sample successively with absolute ethanol and deionized water, and then put the sample into a vacuum drying oven at 60 °C for vacuum drying for 24 h to obtain the acrylate copolymer material.

[0031] Example 3

[0032] (1) Put 1.2 g of phenethyl acrylate, 0.60 g of ethylene glycol phenyl ether methacrylate, 0.04 g of 1,4-butanediol diacrylate, and 0.008 g of azobisisobutyronitrile in a beaker, mix and stir for 1 h until the solution is clear to prepare a mixed solution;

[0033] (2) Put the mixed solution into a vacuum drying oven for degassing for 2 h, then inject it into a mold, and then transfer it to an oven at 60 °C for polymerization reaction for 5 h, and then put it into an oven at 110 °C for polymerization reaction for 4 h;

[0034] (3) After the reaction is completed, wait for the sample to cool to room temperature, disassemble the mold and take out the sample. Wash the obtained sample successively with absolute ethanol and deionized water, and then put the sample into a vacuum drying oven at 60 °C for vacuum drying for 24 h to obtain the acrylate copolymer material.

[0035] Example 4

[0036] (1) Put 4.8 g of phenethyl acrylate, 3.2 g of ethylene glycol phenyl ether methacrylate, 0.16 g of 1,4-butanediol diacrylate, and 0.032 g of azobisisobutyronitrile in a beaker, mix and stir for 1 h until the solution is clear to prepare a mixed solution;

[0037] (2) Put the mixed solution into a vacuum drying oven for degassing for 2 h, then inject it into a mold, and then transfer it to an oven at 60 °C for polymerization reaction for 5 h, and then put it into an oven at 110 °C for polymerization reaction for 4 h;

[0038] (3) After the reaction is completed, wait for the sample to cool to room temperature, disassemble the mold and take out the sample. Wash the obtained sample successively with absolute ethanol and deionized water, and then put the sample into a vacuum drying oven at 60 °C for vacuum drying for 24 h to obtain the acrylate copolymer material.

[0039] Example 5

[0040] (1) Place 5.0 g of phenethyl acrylate, 5.0 g of ethylene glycol phenyl ether methacrylate, 0.50 g of 1,4-butanediol diacrylate, and 0.04 g of azobisisobutyronitrile in a beaker, mix and stir for 1 h until the solution is clear to prepare a mixed solution;

[0041] (2) Place the mixed solution in a vacuum drying oven to degas for 2 h, then inject it into a mold, and then transfer it to an oven at 60 °C for polymerization reaction for 5 h, and then place it in an oven at 110 °C for polymerization reaction for 4 h;

[0042] (3) After the reaction is completed, wait for the sample to cool to room temperature, disassemble the mold and take out the sample. Wash the obtained sample successively with anhydrous ethanol and deionized water, and then place the sample in a vacuum drying oven at 60 °C for vacuum drying for 24 h to obtain an acrylate copolymer material.

[0043] Example 6

[0044] (1) Place 7.0 g of phenylbutyl methacrylate, 7.0 g of ethylene glycol phenyl ether acrylate, 0.28 g of 1,4-butanediol diacrylate, and 0.028 g of azobisisobutyronitrile in a beaker, mix and stir for 1 h until the solution is clear to prepare a mixed solution;

[0045] (2) Place the mixed solution in a vacuum drying oven to degas for 2 h, then inject it into a mold, and then transfer it to an oven at 60 °C for polymerization reaction for 5 h, and then place it in an oven at 110 °C for polymerization reaction for 4 h;

[0046] (3) After the reaction is completed, wait for the sample to cool to room temperature, disassemble the mold and take out the sample. Wash the obtained sample successively with anhydrous ethanol and deionized water, and then place the sample in a vacuum drying oven at 60 °C for vacuum drying for 24 h to obtain an acrylate copolymer material.

[0047] Example 7

[0048] (1) Place 7.0 g of phenylbutyl methacrylate, 7.0 g of ethylene glycol phenyl ether acrylate, 0.28 g of 1,4-butanediol diacrylate, and 0.060 g of azobisisobutyronitrile in a beaker, mix and stir for 1 h until the solution is clear to prepare a mixed solution;

[0049] (2) Place the mixed solution in a vacuum drying oven to degas for 2 h, then inject it into a mold, and then transfer it to an oven at 60 °C for polymerization reaction for 5 h, and then place it in an oven at 110 °C for polymerization reaction for 4 h;

[0050] (3) After the reaction is completed, wait for the sample to cool to room temperature, disassemble the mold and take out the sample. Wash the obtained sample successively with anhydrous ethanol and deionized water, and then place the sample in a vacuum drying oven at 60 °C for vacuum drying for 24 h to obtain an acrylate copolymer material.

[0051] Example 8

[0052] (1)Put 7.0 g of phenylbutyl acrylate, 7.0 g of ethylene glycol phenyl ether methacrylate, 0.84 g of 1,4-butanediol diacrylate, and 0.014 g of azobisisobutyronitrile in a beaker, mix and stir for 1 h until the solution is clear to prepare a mixed solution;

[0053] (2)Put the mixed solution into a vacuum drying oven for degassing for 2 h, then inject it into a mold, and then transfer it to an oven at 60 °C for polymerization reaction for 5 h, and then put it into an oven at 110 °C for polymerization reaction for 4 h;

[0054] (3)After the reaction is completed, wait for the sample to cool to room temperature, disassemble the mold and take out the sample, wash the obtained sample with anhydrous ethanol and deionized water in turn, and then put the sample into a vacuum drying oven at 60 °C for vacuum drying for 24 h to obtain an acrylate copolymer material.

[0055] Example 9

[0056] (1)Put 1.0 g of phenethyl acrylate, 9.0 g of ethylene glycol phenyl ether methacrylate, 0.1 g of 1,4-butanediol dimethacrylate, and 0.05 g of azobisisobutyronitrile in a beaker, mix and stir for 1 h until the solution is clear to prepare a mixed solution;

[0057] (2)Put the mixed solution into a vacuum drying oven for degassing for 1 h, then inject it into a mold, and then transfer it to an oven at 50 °C for polymerization reaction for 20 h, and then put it into an oven at 100 °C for polymerization reaction for 10 h;

[0058] (3)After the reaction is completed, wait for the sample to cool to room temperature, disassemble the mold and take out the sample, wash the obtained sample with anhydrous ethanol and deionized water in turn, wash 3 times each time for 10 min; then put the sample into a vacuum drying oven at 60 °C for vacuum drying for 24 h to obtain an acrylate copolymer material.

[0059] Example 10

[0060] (1)Put 9.0 g of phenylpropyl acrylate, 1.0 g of diphenyl ether methacrylate, 0.1 g of 1,4-butanediol dimethacrylate, and 0.05 g of azobisisobutyronitrile in a beaker, mix and stir for 1 h until the solution is clear to prepare a mixed solution;

[0061] (2)Put the mixed solution into a vacuum drying oven for degassing for 10 h, then inject it into a mold, and then transfer it to an oven at 100 °C for polymerization reaction for 2 h, and then put it into an oven at 150 °C for polymerization reaction for 1 h;

[0062] After the reaction is completed, wait for the sample to cool to room temperature, disassemble the mold and take out the sample. Wash the obtained sample successively with anhydrous ethanol and deionized water, wash 3 times each, 10 minutes each time; then put the sample into a vacuum drying oven at 60 °C and vacuum dry for 24 h to obtain the acrylate copolymer material.

[0063] Example 11

[0064] (1) Put 6.0 g of phenethyl methacrylate, 4.0 g of ethylene glycol phenyl ether acrylate, 0.1 g of 1,6 - hexanediol diacrylate, and 0.05 g of azobisisobutyronitrile in a beaker, mix and stir for 1 h until the solution is clear to prepare a mixed solution;

[0065] (2) Put the mixed solution into a vacuum drying oven to degas for 3 h, then inject it into the mold, and then transfer it to an oven at 65 °C for polymerization reaction for 12 h, and then put it into an oven at 120 °C for polymerization reaction for 6 h;

[0066] After the reaction is completed, wait for the sample to cool to room temperature, disassemble the mold and take out the sample. Wash the obtained sample successively with anhydrous ethanol and deionized water, wash 3 times each, 10 minutes each time; then put the sample into a vacuum drying oven at 60 °C and vacuum dry for 24 h to obtain the acrylate copolymer material.

[0067] Example 12

[0068] (1) Put 3.0 g of phenylbutyl acrylate, 7.0 g of ethylene glycol methacrylate, 1.0 g of 1,4 - butanediol diacrylate, and 0.05 g of azobisisobutyronitrile in a beaker, mix and stir for 1 h until the solution is clear to prepare a mixed solution;

[0069] (2) Put the mixed solution into a vacuum drying oven to degas for 5 h, then inject it into the mold, and then transfer it to an oven at 75 °C for polymerization reaction for 8 h, and then put it into an oven at 130 °C for polymerization reaction for 4 h;

[0070] After the reaction is completed, wait for the sample to cool to room temperature, disassemble the mold and take out the sample. Wash the obtained sample successively with anhydrous ethanol and deionized water, wash 3 times each, 10 minutes each time; then put the sample into a vacuum drying oven at 60 °C and vacuum dry for 24 h to obtain the acrylate copolymer material.

[0071] Example 13

[0072] (1) Put 5.0 g of phenylpropyl methacrylate, 5.0 g of phenyl ether acrylate, 0.5 g of 1,4 - butanediol dimethacrylate, and 0.01 g of azobisisobutyronitrile in a beaker, mix and stir for 1 h until the solution is clear to prepare a mixed solution;

[0073] (2) Put the mixed solution into a vacuum drying oven to degas for 4 h, then inject it into a mold, and then transfer it to an oven at 80 °C for polymerization reaction for 10 h, and then put it into an oven at 140 °C for polymerization reaction for 3 h;

[0074] (3) After the reaction is completed, wait for the sample to cool to room temperature, disassemble the mold and take out the sample. Wash the obtained sample with anhydrous ethanol and deionized water successively, wash 3 times each, 10 min each time; then put the sample into a vacuum drying oven at 60 °C for vacuum drying for 24 h to obtain an acrylate copolymer material.

[0075] Example 14

[0076] (1) Put 4.0 g of phenethyl acrylate, 6.0 g of ethylene glycol phenyl ether methacrylate, 0.5 g of 1,6 - hexanediol diacrylate, and 0.5 g of azobisisobutyronitrile in a beaker, mix and stir for 1 h until the solution is clear to prepare a mixed solution;

[0077] (2) Put the mixed solution into a vacuum drying oven to degas for 6 h, then inject it into a mold, and then transfer it to an oven at 90 °C for polymerization reaction for 6 h, and then put it into an oven at 135 °C for polymerization reaction for 5 h;

[0078] (3) After the reaction is completed, wait for the sample to cool to room temperature, disassemble the mold and take out the sample. Wash the obtained sample with anhydrous ethanol and deionized water successively, wash 3 times each, 10 min each time; then put the sample into a vacuum drying oven at 60 °C for vacuum drying for 24 h to obtain an acrylate copolymer material.

[0079] Example 15

[0080] (1) Put 2.0 g of phenethyl acrylate, 8.0 g of ethylene glycol phenyl ether acrylate, 0.2 g of 1,4 - butanediol diacrylate, and 0.05 g of azobisisobutyronitrile in a beaker, mix and stir for 1 h until the solution is clear to prepare a mixed solution;

[0081] (2) Put the mixed solution into a vacuum drying oven to degas for 7 h, then inject it into a mold, and then transfer it to an oven at 50 °C for polymerization reaction for 20 h, and then put it into an oven at 100 °C for polymerization reaction for 1 h;

[0082] After the reaction is completed, wait for the sample to cool to room temperature, disassemble the mold and take out the sample. Wash the obtained sample successively with anhydrous ethanol and deionized water, each washing 3 times for 10 minutes each time. Then place the sample in a vacuum drying oven at 60 °C and vacuum dry for 24 hours to obtain the acrylate copolymer material.

[0083] Example 16

[0084] (1) Put 8.0 g of phenylbutyl methacrylate, 2.0 g of diphenyl ether methacrylate, 0.2 g of 1,4 - butanediol dimethacrylate, and 0.05 g of azobisisobutyronitrile in a beaker, mix and stir for 1 h until the solution is clear to prepare a mixed solution.

[0085] (2) Put the mixed solution into a vacuum drying oven to degas for 8 h, then inject it into a mold, and then transfer it to an oven at 100 °C for polymerization reaction for 2 h, and then put it into an oven at 150 °C for polymerization reaction for 10 h.

[0086] After the reaction is completed, wait for the sample to cool to room temperature, disassemble the mold and take out the sample. Wash the obtained sample successively with anhydrous ethanol and deionized water, each washing 3 times for 10 minutes each time. Then place the sample in a vacuum drying oven at 60 °C and vacuum dry for 24 hours to obtain the acrylate copolymer material.

[0087] According to the following method, the optical properties and mechanical properties of the copolymer materials provided in some examples were tested.

[0088] 1. Transmittance measurement experiment:

[0089] Use a UV - visible spectrophotometer (SHIMADZU UV - 1780 type) to measure the transmittance of the copolymer material. First, cut the material into long strip - shaped thin slices with a size of 1 cm×3 cm×0.04 cm, put them into a cuvette filled with physiological saline, set the scanning wavelength range to 200 - 800 nm, and perform transmittance detection after calibrating the baseline.

[0090] 2. Refractive index measurement experiment:

[0091] Use an Abbe refractometer (WAY - 2S type) to measure the refractive index of the copolymer material. First, cut the material into square thin slices with a size of 1 cm×1 cm×0.04 cm, use the Abbe refractometer for measurement, and record the reading of the Abbe refractometer.

[0092] 3. Mechanical property measurement experiment:

[0093] Tensile strength refers to the ratio of the maximum tensile force a material experiences before rupture to the cross-sectional area of the material, i.e., stress. Elongation at break is the percentage of the elongation distance of the original gauge length to the original gauge length after the material is stretched and fractured. Tensile strength is an important parameter for measuring the mechanical properties of materials, and elongation at break is an important parameter indicating the uniform or stable deformation of materials. Prepare 3 standard dumbbell-shaped samples, and use a tensile testing machine of model 7000ZS to measure the tensile strength and elongation at break of the material, record the data, and take the average value.

[0094] 4. DSC Flexibility Determination Experiment:

[0095] Use a differential scanning calorimeter (NETZSCH DSC 200F3 type) to measure the glass transition temperature of the IOL material. Put about 5 mg of the dried sample into the test crucible, and the temperature scanning range is from -20 to 90 °C, with a speed of 5 °C / min.

[0096] Figure 2 It is a refractive index measurement diagram of the copolymer materials of Examples 1-6. Among them, a is the copolymer material of Example 1, b is the copolymer material of Example 2, c is the copolymer material of Example 3, d is the copolymer material of Example 4, e is the copolymer material of Example 5, and f is the copolymer material of Example 6. It can be analyzed from the figure that the refractive indices of all copolymer materials are above 1.55, and the optical properties are excellent.

[0097] Figure 3 It is a mechanical property measurement diagram of the copolymer materials of Examples 1-6. Among them, a is the group of copolymer materials of Example 2, b is the group of copolymer materials of Example 1, c is the group of copolymer materials of Example 4, and d is the group of copolymer materials of Example 3. It is shown by the analysis from the figure that as the monomer ratio changes, the tensile strength of the copolymer material continuously increases, and the elongation at break shows a trend of first increasing and then decreasing. The copolymer material in Group B has the highest elongation at break. At this time, the material has the best toughness, and the tensile strength is greater than 3.5 MPa at this time, and the mechanical properties are the best.

[0098] Figure 4 It is a DSC measurement diagram of the copolymer material of Example 2. Through the analysis in the figure, it can be found that the glass transition temperature of the copolymer material is 14.64 °C, which meets the industry standard of the commercial intraocular lens copolymer material being lower than 20 °C. The material has good flexibility and is convenient for unfolding and folding during surgery.

[0099] Experiments show that, compared with the prior art, the optical properties of the present invention are better, with a refractive index exceeding 1.55. Against the background of the increasing requirements for the refractive index of intraocular lens materials in cataract surgery, the technical solution of the present invention can better meet the demand for the refractive index of materials in minimally invasive surgery and provide higher visual quality for patients. The copolymer prepared by the present invention has a glass transition temperature lower than 20°C and a tensile strength greater than 3.5 MPa, achieving a balance between mechanical properties and flexibility and meeting the minimally invasive implantation requirements of intraocular lenses that can be folded and easily unfolded. The preparation process of the present invention is more concise, which is conducive to reducing the production difficulty and cost, and the solution has strong repeatability. The copolymer prepared by the present invention has both ultraviolet protection functions, can effectively block the radiation in the UV-C band to protect the retina; the protection function for the retina is more targeted and clear.

[0100] The above description of the embodiments is only used to help understand the method and its core idea of the present invention. The above description of the disclosed embodiments enables those skilled in the art to implement or use the present invention. Various modifications to these embodiments will be obvious to those skilled in the art, and the general principles defined herein can be implemented in other embodiments without departing from the spirit or scope of the present invention. Therefore, for those of ordinary skill in the art in this technical field, without departing from the principle of the present invention, all equal changes and modifications made according to the scope of the patent application of the present invention shall fall within the scope covered by the present invention. The present invention will not be limited to these embodiments shown herein, but will conform to the widest scope consistent with the principles and novel features disclosed herein.

Claims

1. A preparation method of a flexible acrylate copolymer with high optical performance, characterized in that It includes the following steps: 1) Put the first monomer, the second monomer, the crosslinking agent and the initiator into a beaker, mix and stir until the solution is clear to obtain a mixed solution; the first monomer is selected from at least one of phenethyl acrylate, phenylpropyl acrylate, phenethyl methacrylate, phenylpropyl methacrylate, phenylbutyl acrylate, and phenylbutyl methacrylate; the second monomer is selected from at least one of phenyl ether acrylate, ethylene glycol phenyl ether acrylate, diphenyl ether methacrylate, ethylene glycol methacrylate, and ethylene glycol phenyl ether methacrylate; 2) Carry out vacuum degassing on the mixed solution, inject the mixed solution into a mold, and put the mold into an oven for two-stage heating polymerization; 3) After the reaction is completed, wait for the sample to cool to room temperature, disassemble the mold and take out the sample, wash the obtained sample successively with absolute ethanol and deionized water, and dry it to obtain a copolymer material.

2. The preparation method of a flexible acrylate copolymer with high optical performance according to claim 1, characterized in that In step 1), the weight ratio of the first monomer to the second monomer is (1:9) to (9:1).

3. The preparation method of a flexible acrylate copolymer with high optical performance as described in claim 1, characterized in that In step 1), the addition amount of the crosslinking agent is 1% to 10% of the total weight of the first monomer and the second monomer.

4. The preparation method of a flexible acrylate copolymer with high optical performance as described in claim 1, characterized in that In step 1), the addition amount of the initiator is 0.1% to 5% of the total weight of the first monomer and the second monomer.

5. The preparation method of a flexible acrylate copolymer with high optical performance according to claim 1, characterized in that In step 1), the crosslinking agent is selected from at least one of 1,4-butanediol diacrylate, 1,4-butanediol dimethacrylate, and 1,6-hexanediol diacrylate.

6. The preparation method of a flexible acrylate copolymer with high optical performance according to claim 1, characterized in that In step 1), the initiator used is azobisisobutyronitrile.

7. The preparation method of a flexible acrylate copolymer with high optical performance as described in claim 1, characterized in that In step 2), the degassing time is 1 to 10 h.

8. The preparation method of a flexible acrylate copolymer with high optical performance according to claim 1, characterized in that In step 2), the specific conditions of the two-stage heating polymerization are that the temperature in the first stage is 50 to 100 °C and the reaction time is 2 to 20 h; the temperature in the second stage is 100 to 150 °C and the reaction time is 1 to 10 h.

9. A flexible hydrophobic acrylate copolymer with high optical performance is prepared by using the preparation method of a flexible acrylate copolymer with high optical performance as described in any one of claims 1 to 8.

10. Use of a flexible hydrophobic acrylate copolymer with high optical performance as described in claim 9 in the preparation of intraocular lens materials.

Citation Information

Patent Citations

  • Foldable artificial lens material and preparation method thereof

    CN106632826A

  • Hydrophobic foldable intraocular lens material with high refractive index and preparation method thereof

    CN110003385A