Optical lens with protection effect and preparation method thereof

Abstract

The invention relates to the technical field of optical lenses, and discloses an optical lens with a protective effect and a preparation method thereof.The optical lens is prepared by using an initiator to initiate cross-linking polymerization of methyl methacrylate and a functional monomer and then performing degassing, drying and injection molding processes. Wherein a functional monomer structure contains a large number of unsaturated alkenyl functional groups, and can be subjected to cross-linking polymerization with methyl methacrylate under the action of an initiator, so that a large number of tertiary butyl, biphenyl and rigid benzene ring structures are introduced into an acrylic molecular chain, and meanwhile, the acrylic molecular chain is converted into a three-dimensional structure from a straight chain; wherein the tertiary butyl, benzene ring and biphenyl structures all have extremely strong hydrophobicity, so that the acrylic lens has a super-hydrophobic surface and is endowed with good stain resistance, in addition, the rigid structure and the three-dimensional network can improve the hardness and compactness of the lens and reduce the width of a grinding crack of a hard substance on the surface of a coating, so that the wear resistance of the lens is improved.

Description

Technical Field

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

[0002] With the rapid advancement of optical technology, traditional glass lenses are increasingly facing challenges due to limitations such as heavy weight and fragility. Polymer materials such as polymethyl methacrylate (PMMA, commonly known as acrylic) are emerging as new products in the optical field, thanks to their lightweight, high light transmittance, and excellent processing properties. From consumer electronics to medical devices, 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 lenses may become contaminated during use, they need to be wiped frequently to keep them clean and tidy. However, since acrylic is a polymer material with strong lipophilicity, it is actually difficult to wipe off oily stains. In addition, some hard substances may cause scratches on the lenses during the wiping process, shortening the service life of the lenses. In summary, the current acrylic organic lenses still have obvious problems in actual use. Therefore, it is urgent to develop modification technology to modify acrylic lenses, enhance their wear resistance, and give them good stain resistance. Summary of the Invention

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

[0005] The purpose of the present invention can be achieved through the following technical solutions:

[0006] An optical lens with a protective effect, made of the following raw materials in parts by weight:

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

[0008] As a further embodiment of the present invention, the method for preparing the functional monomer comprises the following steps:

[0009] Step 1, nitrogen is introduced into the reactor, and then 3,5-di-tert-butylbenzoic acid and acetone are added to the reactor. After stirring evenly, a condensing agent and a catalyst are added to the reactor. After the addition is completed, the mixture is stirred at room temperature for 20-30 minutes. Then, 1,3-diglycidyl ether glycerol is added to the reactor, stirred evenly, and then the temperature is increased to 30-40°C. The mixture is stirred at this temperature for 2-4 hours, and the solvent is removed by rotary evaporation. The product is collected to obtain an intermediate product;

[0010] Step 2: Add the intermediate product, 3,3'-di(allyloxy)-[1,1'-biphenyl]-4,4'-diamine and N,N-dimethylformamide to the polymerization kettle. After the addition is completed, nitrogen protection is applied and stirring is started. After a uniform solution is formed, heating is started and the heating rate is controlled to be 2-4°C / min. The temperature is raised to 80-90°C. After stirring for 12-24 hours, the temperature is lowered and the material is discharged. The product is collected to obtain a functional monomer.

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

[0012] As a further embodiment of the present invention, in step 1, the condensing agent is dicyclohexylcarbodiimide or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide.

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

[0014] As a further embodiment of the present invention, in step 2, the molar ratio of the intermediate product to 3,3'-bi(allyloxy)-[1,1'-biphenyl]-4,4'-diamine is 1:1.

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

[0016] As a further embodiment of the present invention, the initiator is any one of azobisisobutyronitrile, azobisisoheptanenitrile, benzoyl peroxide or dicumyl peroxide.

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

[0018] A method for preparing an optical lens with a protective effect comprises the following steps:

[0019] Step 1: Add methyl methacrylate, functional monomer and initiator into the polymerization kettle, stir evenly, turn on the heating, raise the temperature to 75-82°C, keep stirring for 1-2 hours, stop heating, and wait for it to cool to room temperature to form a pre-polymerization material;

[0020] The second step is to add a blue light absorber to the prepolymer material, stir and mix it evenly, then transfer the formed mixture to a degasser, control the pressure to 1-2kPa, and degas at room temperature. Then restore the normal pressure, place it in an oven, and dry it at a temperature of 100-120°C. Finally, at a temperature of 200-230°C, inject it into a mold, demold it, and then you can make an optical lens.

[0021] Beneficial effects of the present invention:

[0022] The functional monomer structure prepared by the present invention contains a large number of unsaturated olefinic functional groups, which can undergo cross-linking polymerization with methyl methacrylate under the action of an initiator, thereby introducing a large number of tert-butyl groups, biphenyl groups, and rigid benzene ring structures into the acrylic molecular chain, and at the same time converting the acrylic molecular chain from a straight chain into a three-dimensional structure. On the one hand, the tert-butyl groups, benzene rings, and biphenyl structures all have extremely strong hydrophobicity, which can make the acrylic lens have a super-hydrophobic surface and impart good stain resistance to the lens. On the other hand, the rigid structure and three-dimensional network can increase the hardness and density of the lens, reduce the width of the wear scar of the hard substance on the coating surface, and thus improve the wear resistance of the lens.

[0023] The present invention provides the lens with good blue light protection effect by adding a blue light absorber into the lens.

[0024] Of course, any product implementing the present invention does not necessarily need to achieve all of the advantages described above at the same time. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the following briefly introduces the drawings required for describing the embodiments. Obviously, the drawings described below are only some embodiments of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without creative work.

[0026] Figure 1 This is the infrared test image of the functional monomer. DETAILED DESCRIPTION

[0027] The following will clearly and completely describe the technical solutions in the embodiments of the present invention in conjunction with the accompanying drawings. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without making any creative efforts shall fall within the scope of protection of the present invention.

[0028] Preparation Example

[0029] Preparation of functional monomers:

[0030] Step 1, nitrogen is introduced into the reactor, and then 0.3g of 3,5-di-tert-butylbenzoic acid and acetone are added to the reactor. After stirring evenly, 0.1g of dicyclohexylcarbodiimide and 0.04g of 4-dimethylaminopyridine are added to the reactor. After the addition is completed, stirring is carried out at room temperature for 30 minutes. Then, 0.26g of 1,3-diglycidyl ether glycerol is added to the reactor. After stirring evenly, the temperature is raised to 35°C, and the mixture is stirred for 3 hours. The solvent is removed by rotary evaporation, and the product is collected to obtain an intermediate product;

[0031] Step 2: Add 0.2 g of the intermediate product, 0.14 g of 3,3'-di(allyloxy)-[1,1'-biphenyl]-4,4'-diamine and N,N-dimethylformamide to the polymerization kettle. After the addition is completed, nitrogen protection is applied and stirring is started. After a uniform solution is formed, heating is started and the heating rate is controlled to be 3°C / min. The temperature is raised to 90°C. After stirring for 18 hours, the temperature is lowered and the material is discharged. The product is collected to obtain a functional monomer.

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

[0033] Example 1

[0034] An optical lens with a protective effect, made of the following raw materials in parts by weight:

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

[0036] The method for preparing the optical lens comprises the following steps:

[0037] The first step is to add methyl methacrylate, functional monomer and initiator azobisisobutyronitrile into the polymerization kettle, stir evenly, turn on the heating, raise the temperature to 80 ° C, keep stirring for 1 hour, stop heating, and wait for it to cool to room temperature to form a pre-polymerization material;

[0038] The second step is to add the blue light absorber lutein to the prepolymer material. After the addition, stir and mix evenly. Then transfer the formed mixture to a degasser, control the pressure to 1kPa, and degas at room temperature. Then restore the normal pressure and place it in an oven at 100°C for drying. Finally, at 200°C, inject it into a mold for molding and demold it to obtain an optical lens.

[0039] Example 2

[0040] An optical lens with a protective effect, made of the following raw materials in parts by weight:

[0041] 68 parts of methyl methacrylate, 5.5 parts of functional monomer, 0.2 parts of initiator azobisisoheptanenitrile, and 2 parts of blue light absorber lutein.

[0042] The method for preparing the optical lens comprises the following steps:

[0043] The first step is to add methyl methacrylate, functional monomer and initiator azobisisoheptanenitrile into a polymerization kettle, stir evenly, turn on the heating, raise the temperature to 80 ° C, keep stirring for 1.5 hours, stop heating, and wait for it to cool to room temperature to form a pre-polymerization material;

[0044] The second step is to add the blue light absorber lutein to the prepolymer material. After the addition, stir and mix evenly. Then transfer the formed mixture to a degasser, control the pressure to 1kPa, and degas at room temperature. Then restore the normal pressure and place it in an oven at a temperature of 110°C for drying. Finally, at a temperature of 220°C, inject it into a mold for molding and demold it to obtain an optical lens.

[0045] Example 3

[0046] An optical lens with a protective effect, made of the following raw materials in parts by weight:

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

[0048] The method for preparing the optical lens comprises the following steps:

[0049] The first step is to add methyl methacrylate, functional monomer and initiator benzoyl peroxide into the polymerization kettle, stir evenly, turn on the heating, raise the temperature to 82 ° C, keep stirring for 2 hours, stop heating, and wait for it to cool to room temperature to form a pre-polymerization material;

[0050] The second step is to add the blue light absorber lutein to the prepolymer material. After the addition, stir and mix evenly. Then transfer the formed mixture to a degasser, control the pressure to 2kPa, and degas at room temperature. Then restore the normal pressure and place it in an oven at a temperature of 120°C for drying. Finally, at a temperature of 230°C, inject it into a mold for molding and demold it to obtain an optical lens.

[0051] Comparative Example 1

[0052] An optical lens with a protective effect, made of the following raw materials in parts by weight:

[0053] 68 parts of methyl methacrylate, 0.2 parts of initiator azobisisoheptanenitrile, and 2 parts of blue light absorber lutein.

[0054] The method for preparing the optical lens comprises the following steps:

[0055] The first step is to add methyl methacrylate and initiator azobisisoheptanenitrile into a polymerization kettle, stir evenly, turn on the heating, raise the temperature to 80 ° C, keep stirring for 1.5 hours, stop heating, and wait for it to cool to room temperature to form a pre-polymerization material;

[0056] The second step is to add the blue light absorber lutein to the prepolymer material. After the addition, stir and mix evenly. Then transfer the formed mixture to a degasser, control the pressure to 1kPa, and degas at room temperature. Then restore the normal pressure and place it in an oven at a temperature of 110°C for drying. Finally, at a temperature of 220°C, inject it into a mold for molding and demold it to obtain an optical lens.

[0057] Performance Testing

[0058] The optical lenses in the examples and comparative examples were made into test samples that met the specifications and subjected to various performance tests:

[0059] According to the standard ASTM D7334-2008, the water contact angle test is carried out. Generally speaking, the larger the water contact angle, the better the anti-fouling performance;

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

[0061] Use an ultraviolet spectrophotometer to test the harmful blue light transmittance of the sample at a wavelength of 400nm;

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

[0063] Analysis and test results show that the optical lens prepared in the embodiment of the present invention has good wear resistance and anti-fouling properties. After the functional monomer is removed, a three-dimensional network structure cannot be formed, and the rigid structure and tert-butyl hydrophobic group in the functional monomer structure cannot be utilized, so the anti-fouling and wear resistance are significantly reduced.

[0064] Specific examples are used herein to illustrate the principles and implementation methods of the present invention. The description of the above embodiments is only used to help understand the method of the present invention and its core ideas, including the best mode, and also enable any technician in the field to practice the present invention, including making and using any device or system, and implementing any combined method. It should be pointed out that for ordinary technicians in this technical field, without departing from the principles of the present invention, several improvements and modifications can be made to the present invention, and these improvements and modifications also fall within the scope of protection of the claims of the present invention. The scope of patent protection of the present invention is defined by the claims and may include other embodiments that can be thought of by those skilled in the art. If these other embodiments have structural elements similar to the literal description of the claims, or if they include equivalent structural elements that are not substantially different from the literal description of the claims, then these other embodiments should also be included in the scope of the claims.

[0065] The above embodiments are only used to illustrate the technical solutions of the present invention, rather than to limit the same. Although the present invention has been described in detail with reference to the aforementioned embodiments, those skilled in the art should understand that they can still modify the technical solutions described in the aforementioned embodiments, or make equivalent replacements for some of the technical features therein. However, these modifications or replacements will not cause the essence of the corresponding technical solutions to deviate from the spirit and scope of the technical solutions of the various embodiments of the present invention.

Claims

1. An optical lens with a protective effect, characterized in that: The invention is prepared by using the following raw materials in parts by weight: 65-75 parts of methyl methacrylate, 3-6 parts of functional monomer, 0.1-0.3 parts of initiator, 1-3 parts of blue light absorber.

2. The optical lens with protective effect according to claim 1, characterized in that: The preparation method of the functional monomer comprises the following steps: Step 1, nitrogen is introduced into the reactor, and then 3,5-di-tert-butylbenzoic acid and acetone are added to the reactor. After stirring evenly, a condensing agent and a catalyst are added to the reactor. After the addition is completed, the mixture is stirred at room temperature for 20-30 minutes. Then, 1,3-diglycidyl ether glycerol is added to the reactor, stirred evenly, and then the temperature is increased to 30-40°C. The mixture is stirred at this temperature for 2-4 hours, and the solvent is removed by rotary evaporation. The product is collected to obtain an intermediate product; Step 2: Add the intermediate product, 3,3'-di(allyloxy)-[1,1'-biphenyl]-4,4'-diamine and N,N-dimethylformamide to the polymerization kettle. After the addition is completed, nitrogen protection is applied and stirring is started. After a uniform solution is formed, heating is started and the heating rate is controlled to be 2-4°C / min. The temperature is raised to 80-90°C. After stirring for 12-24 hours, the temperature is lowered and the material is discharged. The product is collected to obtain a functional monomer.

3. The optical lens with protective effect according to claim 2, characterized in that: In step 1, the molar ratio of 3,5-di-tert-butylbenzoic acid to 1,3-diepoxyglyceryl ether glycerol is 1:

1.

4. The optical lens with protective effect according to claim 2, characterized in that: In step 1, the condensing agent is dicyclohexylcarbodiimide or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide.

5. The optical lens with protective effect according to claim 2, characterized in that: In step 1, the catalyst is any one of 4-dimethylaminopyridine, N-hydroxysuccinimide or 1-hydroxybenzotriazole.

6. The optical lens with protective effect according to claim 2, characterized in that: In step 2, the molar ratio of the intermediate product to 3,3'-bi(allyloxy)-[1,1'-biphenyl]-4,4'-diamine is 1:

1.

7. The optical lens with protective effect according to claim 1, characterized in that: The initiator is any one of azobisisobutyronitrile, azobisisoheptanenitrile, benzoyl peroxide or dicumyl peroxide.

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

9. A method for preparing an optical lens with a protective effect as claimed in claim 1, characterized in that: The following steps are involved: Step 1: Add methyl methacrylate, functional monomer and initiator into the polymerization kettle, stir evenly, turn on the heating, raise the temperature to 75-82°C, keep stirring for 1-2 hours, stop heating, and wait for it to cool to room temperature to form a pre-polymerization material; The second step is to add a blue light absorber to the prepolymer material, stir and mix it evenly, then transfer the formed mixture to a degasser, control the pressure to 1-2kPa, and degas at room temperature. Then restore the normal pressure, place it in an oven, and dry it at a temperature of 100-120°C. Finally, at a temperature of 200-230°C, inject it into a mold, demold it, and then you can make an optical lens.

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