Optical lens with a protective effect and method for manufacturing same

Abstract

The application relates to the technical field of optical lenses, and discloses an optical lens with a protection effect and a preparation method thereof. The optical lens is prepared through the crosslinking polymerization of methyl methacrylate and a functional monomer by using an initiator, and is prepared through a degassing, drying and injection molding process. The functional monomer structure contains a large number of unsaturated alkenyl functional groups, which can be crosslinked and polymerized with the methyl methacrylate under the action of the initiator, so that a large number of tertiary butyl groups, biphenyl and rigid benzene ring structures are introduced into the acrylic molecular chain, and the acrylic molecular chain is converted from a straight chain into a three-dimensional structure. The tertiary butyl groups, the benzene ring and the biphenyl structure all have strong hydrophobicity, the acrylic lens has a super-hydrophobic surface, the lens has good stain resistance, in addition, the rigid structure and the three-dimensional network can improve the hardness and density of the lens, reduce the width of the grinding marks of hard substances on the coating surface, and improve the wear resistance of the lens.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of optical lenses, in particular to an optical lens with a protective effect and a preparation method thereof. BACKGROUND

[0002] In today's rapid development of optical technology, traditional glass lenses are gradually facing challenges due to their heavy weight, fragility and other limitations, while high molecular materials represented by polymethyl methacrylate (PMMA, commonly known as acrylic) are becoming emerging products in the optical field due to their lightweight, high light transmittance and excellent processing performance. From consumer electronics to medical equipment, from the automotive industry to aerospace, acrylic optical lenses are reshaping the design logic of optical products with their unique advantages, driving the industry towards more efficient and sustainable development.

[0003] Since the lens will be contaminated during use, it needs to be wiped frequently to keep the lens clean and tidy. However, since acrylic is a high molecular material with strong lipophilicity, oily stains are actually difficult to wipe, and some hard substances in the wiping process can cause scratches on the lens, reducing the service life of the lens. In summary, the acrylic organic lens at the present stage still has obvious problems in actual use, therefore, it is urgent to develop a modification technology to modify the acrylic lens, enhance its wear resistance, and endow it with good stain resistance. SUMMARY

[0004] In order to solve the problems mentioned in the background art, the purpose of the present application is to provide an optical lens with a protective effect and a preparation method thereof.

[0005] The purpose of the present application can be achieved by the following technical solutions:

[0006] An optical lens with a protective effect is made of the following raw materials by weight fraction:

[0007] Methyl methacrylate 65-75 parts, functional monomer 3-6 parts, initiator 0.1-0.3 parts, blue light absorber 1-3 parts.

[0008] As a further scheme of the present application, the preparation method of the functional monomer comprises the following steps:

[0009] Step one, nitrogen is introduced into the reaction kettle, then 3,5-di-tert-butyl benzoic acid and acetone are added into the reaction kettle, after stirring uniformly, the condensing agent and catalyst are continuously added into the reaction kettle, after completion of addition, the reaction kettle is stirred at room temperature for 20-30 min, then 1,3-diepoxy glycerol ether glycerol is added into the reaction kettle, after stirring, the temperature is increased to 30-40℃, and the mixture is stirred and kept for 2-4 h, then the solvent is removed by rotary evaporation, and the product is collected to prepare an intermediate product;

[0010] Step two, the intermediate product, 3,3'-bis(allyloxy)-[1,1'-biphenyl]-4,4'-diamine and N,N-dimethylformamide are added into the polymerization kettle, after adding, nitrogen protection is started, stirring is started, after forming a uniform solution, heating is started, the temperature is increased to 80-90℃ at a rate of 2-4℃ / min, after 12-24h of temperature maintaining and stirring, the temperature is decreased and the product is collected, thereby the functional monomer is prepared.

[0011] As a further scheme of the present application, in step one, the molar ratio of 3,5-di-tert-butylbenzoic acid and 1,3-diglycidyl glycerol ether glycerol is 1:1.

[0012] As a further scheme of the present application, in step one, the condensing agent is dicyclohexyl carbodiimide or 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide.

[0013] As a further scheme of the present application, in step one, the catalyst is any one of 4-dimethylaminopyridine, N-hydroxysuccinimide or 1-hydroxybenzotriazole.

[0014] As a further scheme of the present application, in step two, the molar ratio of the intermediate product and 3,3'-bis(allyloxy)-[1,1'-biphenyl]-4,4'-diamine is 1:1.

[0015] In the above technical solution, first, the carboxyl group of 3,5-di-tert-butylbenzoic acid is activated by using a catalyst and a condensing agent, then 1,3-diglycidyl glycerol ether glycerol is used as a reactant to perform esterification condensation reaction with the hydroxyl group in its structure, thereby an intermediate product containing two equivalent epoxy substituents in the structure is prepared, then 3,3'-bis(allyloxy)-[1,1'-biphenyl]-4,4'-diamine is used as a chain extender, two equivalent amino substituents in its structure can perform continuous ring-opening addition reaction with the intermediate product, thereby a functional monomer containing a large number of unsaturated alkenyl functional groups, a large number of biphenyl and rigid benzene ring structures in the structure is prepared.

[0016] As a further scheme of the present application, the initiator is any one of azobisisobutyronitrile, azobisisoheptyl nitrile, benzoyl peroxide or dicumyl peroxide.

[0017] As a further scheme of the present application, the blue light absorber is lutein.

[0018] A preparation method of an optical lens with a protective effect, comprising the following steps:

[0019] The first step, methyl methacrylate, functional monomer and initiator are added into a polymerization kettle, after stirring uniformly, heating is started, the temperature is increased to 75-82℃, after 1-2h of preservation and stirring, heating is stopped, and the mixture is cooled to room temperature to form a polymerization pre-material;

[0020] The second step, blue light absorber is added into the polymerization pre-material, after addition, stirring and mixing are uniformly carried out, then the formed mixture is transferred into a degassing machine, the pressure is controlled to 1-2kPa, and the degassing treatment is carried out at room temperature, then normal pressure is recovered, the mixture is placed in an oven, and the drying treatment is carried out at a temperature of 100-120℃, finally, the mixture is injection molded into a mold at a temperature of 200-230℃ to form an optical lens.

[0021] The beneficial effects of the present application are as follows:

[0022] The functional monomer prepared in the present application contains a large number of unsaturated alkenyl functional groups in the structure, which can be crosslinked and polymerized with methyl methacrylate under the action of an initiator, thereby introducing a large number of tertiary butyl groups and biphenyl and rigid benzene ring structures into the acrylic molecular chain, and converting the acrylic molecular chain from a straight chain to a three-dimensional structure. On the one hand, the tertiary butyl group, benzene ring and biphenyl structure all have strong hydrophobicity, which can make the acrylic lens have a super-hydrophobic surface, and endow the lens with good stain resistance. On the other hand, the rigid structure and three-dimensional network can improve the hardness and density of the lens, reduce the width of the grinding marks of hard substances on the coating surface, and thereby improve the wear resistance of the lens.

[0023] The present application adds a blue light absorber into the lens to endow the lens with good blue light protection effect.

[0024] Of course, it is not necessary for any product implementing the present application to achieve all the advantages described above at the same time. BRIEF DESCRIPTION OF DRAWINGS

[0025] In order to more clearly illustrate the technical solutions of the embodiments of the present application, the drawings needed for the embodiment description will be briefly introduced as follows. Obviously, the drawings in the following description are only some embodiments of the present application, and other drawings can also be obtained by those skilled in the art without creative labor.

[0026] Figure 1 The infrared test diagram of the functional monomer. DETAILED DESCRIPTION

[0027] With reference to the accompanying drawings: clear and complete description will be given to the technical solutions in the embodiments of the present application. Obviously, the described embodiments are only a part of the embodiments of the present application, rather than all the embodiments. Based on the embodiments in the present application, all other embodiments obtained by a person of ordinary skill in the art without creative labor fall within the scope of the present application.

[0028] Preparation Example

[0029] Preparation of functional monomer:

[0030] Step one, nitrogen was introduced into the reaction kettle, then 0.3g of 3,5-di-tert-butyl benzoic acid and acetone were added into the reaction kettle, after stirring uniformly, 0.1g of dicyclohexyl carbodiimide and 0.04g of 4-dimethylamino pyridine were added into the reaction kettle, after completion of addition, the reaction kettle was stirred at room temperature for 30min, then 0.26g of 1,3-diglyceryl ether glycerol was added into the reaction kettle, after stirring uniformly, the temperature was increased to 35℃, and the reaction kettle was kept stirring for 3h, then the solvent was removed by rotary evaporation, and the product was collected to prepare an intermediate product;

[0031] Step two, 0.2g of the intermediate product, 0.14g of 3,3'-bis(allyloxy)-[1,1'-biphenyl]-4,4'-diamine and N,N-dimethylformamide were added into the polymerization kettle, after completion of addition, nitrogen protection was started, and stirring was started, after a uniform solution was formed, heating was started, and the temperature increasing rate was controlled to be 3℃ / min, the temperature was increased to 90℃, and the reaction kettle was kept stirring for 18h, then the temperature was decreased to take out the product, and the functional monomer was prepared.

[0032] Figure 1 The infrared analysis test diagram of the functional monomer is shown in the figure, the characteristic absorption peak appearing at 3421cm -1 -1 is the N-H characteristic absorption peak of secondary amino group, the characteristic absorption peak appearing at 3329cm -1 -1 is the characteristic absorption peak of hydroxyl group produced by ring opening reaction, the characteristic absorption peak appearing at 3000~3100cm -1 -1 is the C-H characteristic absorption peak in benzene ring structure, the characteristic absorption peak appearing at 2800~3000cm -1 -1 is the saturated aliphatic C-H characteristic absorption peak, the characteristic absorption peak appearing at 1753cm -1 -1 is the ester group C=O characteristic absorption peak, the characteristic absorption peak appearing at 1092cm -1 -1 is the characteristic absorption peak of ether bond.

[0033] Example 1

[0034] An optical lens with protective effect is prepared from the following raw materials by weight:

[0035] Methyl methacrylate 65 parts, functional monomer 3 parts, initiator azobisisobutyronitrile 0.1 part, blue light absorber lutein 1 part.

[0036] The preparation method of the optical lens comprises the following steps:

[0037] Firstly, methyl methacrylate, functional monomer and initiator azobisisobutyronitrile are added into a polymerization kettle, and after being stirred uniformly, heating is started, the temperature is increased to 80℃, and after being kept at 80℃ for 1h, the heating is stopped, and the mixture is cooled to room temperature to form a polymerization precursor;

[0038] Secondly, blue light absorber lutein is added into the polymerization precursor, and after being stirred and mixed uniformly, the formed mixture is transferred into a degassing machine, and is degassed at room temperature under the condition of 1kPa, and then is placed in an oven for drying treatment at 100℃, and finally, is injected into a mold for molding at 200℃, and is demolded to obtain the optical lens.

[0039] Example 2

[0040] An optical lens with a protective effect is prepared by using the following raw materials according to weight parts:

[0041] Methyl methacrylate 68 parts, functional monomer 5.5 parts, initiator azobisisobutyronitrile 0.2 parts, blue light absorber lutein 2 parts.

[0042] The preparation method of the optical lens comprises the following steps:

[0043] Firstly, methyl methacrylate, functional monomer and initiator azobisisobutyronitrile are added into a polymerization kettle, and after being stirred uniformly, heating is started, the temperature is increased to 80℃, and after being kept at 80℃ for 1h, the heating is stopped, and the mixture is cooled to room temperature to form a polymerization precursor;

[0044] Secondly, blue light absorber lutein is added into the polymerization precursor, and after being stirred and mixed uniformly, the formed mixture is transferred into a degassing machine, and is degassed at room temperature under the condition of 1kPa, and then is placed in an oven for drying treatment at 100℃, and finally, is injected into a mold for molding at 200℃, and is demolded to obtain the optical lens.

[0045] Example 3

[0046] An optical lens with a protective effect is prepared by using the following raw materials according to weight parts:

[0047] Methyl methacrylate 75 parts, functional monomer 6 parts, initiator benzoyl peroxide 0.3 parts, blue light absorber lutein 3 parts.

[0048] The preparation method of the optical lens comprises the following steps:

[0049] Firstly, methyl methacrylate, functional monomer and initiator benzoyl peroxide are added into a polymerization kettle, and after being stirred uniformly, heating is started, the temperature is raised to 82℃, and after being kept at the temperature and stirred for 2 hours, the heating is stopped, and the mixture is cooled to room temperature to form a polymerization precursor;

[0050] Secondly, the blue light absorber lutein is added into the polymerization precursor, and after being added completely, the mixture is stirred uniformly, then the formed mixture is transferred into a degassing machine, the pressure is controlled to 2kPa, and the degassing treatment is carried out at room temperature, then the normal pressure is recovered, the mixture is placed in an oven, and the drying treatment is carried out at a temperature of 120℃, finally, the mixture is injection molded into a mold at a temperature of 230℃ to form an optical lens.

[0051] Comparative Example 1

[0052] An optical lens with a protective effect is prepared by using the following raw materials by weight:

[0053] Methyl methacrylate 68 parts, initiator azobis diisopropyl cyanide 0.2 parts, blue light absorber lutein 2 parts.

[0054] The preparation method of the optical lens comprises the following steps:

[0055] Firstly, methyl methacrylate and initiator azobis diisopropyl cyanide are added into a polymerization kettle, and after being stirred uniformly, heating is started, the temperature is raised to 80℃, and after being kept at the temperature and stirred for 1.5 hours, the heating is stopped, and the mixture is cooled to room temperature to form a polymerization precursor;

[0056] Secondly, the blue light absorber lutein is added into the polymerization precursor, and after being added completely, the mixture is stirred uniformly, then the formed mixture is transferred into a degassing machine, the pressure is controlled to 1kPa, and the degassing treatment is carried out at room temperature, then the normal pressure is recovered, the mixture is placed in an oven, and the drying treatment is carried out at a temperature of 110℃, finally, the mixture is injection molded into a mold at a temperature of 220℃ to form an optical lens.

[0057] Performance test

[0058] The optical lenses in the examples and comparative examples are made into test samples conforming to the specifications, and various performance tests are carried out:

[0059] According to the standard ASTM D7334-2008, the water contact angle test is carried out, in general, the larger the water contact angle, the better the stain resistance;

[0060] According to the standard HG / T 4303-2012, the wear resistance test is carried out, the selected weight is 1kg, and the steel wool type is 0000#;

[0061] The harmful blue light transmittance of the sample at 400nm wavelength is tested by the ultraviolet spectrophotometer;

[0062] The test results are shown in the following table:

[0063]

[0064] It can be seen from the analysis of the test results that the optical lens prepared in the embodiment of the application has good wear resistance and stain resistance. After removing the functional monomer, the three-dimensional network structure cannot be formed, and the rigid structure and tertiary butyl hydrophobic groups in the functional monomer structure cannot be utilized, so the stain resistance and wear resistance are obviously decreased.

[0065] The principles and implementation modes of the application are described in this paper by using specific examples, and the above examples are only used to help understand the method and core idea of the application, including the best mode, and also enable any person skilled in the art to practice the application, including manufacturing and using any device or system, and implementing any combined method. It should be noted that for ordinary skilled persons in the art, without departing from the principles of the application, some improvements and modifications can be made to the application, and these improvements and modifications also fall within the protection scope of the claims of the application. The scope of the patent protection of the application is defined by the claims, and can include other embodiments that can be thought of by those skilled in the art. If these other embodiments have structural elements similar to the wording of the claims, or if they include equivalent structural elements that are not substantially different from the wording of the claims, then these other embodiments should also be included in the scope of the claims.

[0066] The above examples are only used to illustrate the technical solutions of the application, and not to limit them; although the application has been described in detail with reference to the foregoing examples, those skilled in the art should understand that they can still modify the technical solutions recorded in the foregoing examples, or make equivalent replacements for some technical features; and these modifications or replacements will not make the essence of the corresponding technical solutions deviate from the spirit and scope of the technical solutions of the embodiments of the application.

Claims

1. An optical lens having a protective effect, characterized in that, The following raw materials are used by weight parts: methyl methacrylate 65-75 parts, functional monomer 3-6 parts, initiator 0.1-0.3 parts, blue light absorber 1-3 parts; The preparation method of the functional monomer comprises the following steps: Step one, nitrogen is introduced into the reaction kettle, then 3,5-di-tert-butyl benzoic acid and acetone are added into the reaction kettle, after stirring, the condensing agent and the catalyst are added into the reaction kettle, after completion of addition, stirring is carried out at room temperature for 20-30 min, then 1,3-diglycidyl ether glycerol is added into the reaction kettle, after stirring, the temperature is increased to 30-40℃, and the mixture is stirred and kept for 2-4 h, then the solvent is removed by rotary evaporation, and the product is collected to prepare an intermediate product; Step two, the intermediate product, 3,3'-bis(allyloxy)-[1,1'-biphenyl]-4,4'-diamine and N,N-dimethylformamide are added into the polymerization kettle, after completion of addition, nitrogen protection is carried out, stirring is started, after a uniform solution is formed, heating is started, the temperature is increased to 80-90℃ at a rate of 2-4℃ / min, and after stirring and keeping for 12-24 h, the temperature is decreased to discharge the product, which is the functional monomer.

2. An optical lens with a protective effect according to claim 1, characterized in that, In step one, the molar ratio of 3,5-di-tert-butyl benzoic acid to 1,3-diglycidyl ether glycerol is 1:

1.

3. The optical lens with a protective effect according to claim 1, characterized in that, In step one, the condensing agent is dicyclohexyl carbodiimide or 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide.

4. The optical lens with a protective effect according to claim 1, characterized in that, In step one, the catalyst is any one of 4-dimethylaminopyridine, N-hydroxysuccinimide or 1-hydroxybenzotriazole.

5. The optical lens with a protective effect according to claim 1, characterized in that, In step two, the molar ratio of the intermediate product to 3,3'-bis(allyloxy)-[1,1'-biphenyl]-4,4'-diamine is 1:

1.

6. The optical lens with a protective effect according to claim 1, characterized in that, The initiator is any one of azobisisobutyronitrile, azobisisoheptyl nitrile, benzoyl peroxide or dicumyl peroxide.

7. The optical lens with a protective effect according to claim 1, characterized in that, The blue light absorber is lutein.

8. A method of manufacturing an optical lens with a protective effect according to claim 1, characterized in that, The following steps are included: First step, methyl methacrylate, functional monomer and initiator are added into the polymerization kettle, after stirring, heating is started, the temperature is increased to 75-82℃, after stirring and keeping for 1-2 h, the heating is stopped, and the mixture is cooled to room temperature to form a polymerization precursor; Second step, the blue light absorber is added into the polymerization precursor, after completion of addition, the mixture is stirred and mixed uniformly, then the mixture is transferred into a degassing machine, the pressure is controlled to be 1-2 kPa, and the mixture is subjected to degassing treatment at room temperature, then the pressure is restored to normal pressure, the mixture is placed in an oven, and subjected to drying treatment at a temperature of 100-120℃, finally, the mixture is injected into a mold to form a product, the product is demolded, and the optical lens is prepared.

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