CN115109186A - 1.60-refractive-index color-changing monomer material, lens and preparation method thereof - Google Patents
1.60-refractive-index color-changing monomer material, lens and preparation method thereof Download PDFInfo
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- CN115109186A CN115109186A CN202210955118.4A CN202210955118A CN115109186A CN 115109186 A CN115109186 A CN 115109186A CN 202210955118 A CN202210955118 A CN 202210955118A CN 115109186 A CN115109186 A CN 115109186A
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- color
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
- C08F222/1025—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate of aromatic dialcohols
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
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- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
- G02C7/10—Filters, e.g. for facilitating adaptation of the eyes to the dark; Sunglasses
- G02C7/102—Photochromic filters
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- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Health & Medical Sciences (AREA)
- Ophthalmology & Optometry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymerisation Methods In General (AREA)
Abstract
The invention belongs to the technical field of optical lenses, and provides a 1.60-refractivity color-changing monomer material, a lens and a preparation method thereof. The 1.60-refractivity color-changing monomer material provided by the invention comprises the following components in parts by weight: 30-50 parts of ethoxylated bisphenol fluorene acrylate, 5-10 parts of dibenzyl maleate, 25-30 parts of ethoxylated bisphenol A acrylate, 18-25 parts of benzene series and 2-5 parts of antioxidant. The lens made of the 1.60-refractivity color-changing monomer material prepared by the invention is qualified in quality, high in color-changing speed and long in service life, and compared with a 1.56-refractivity color-changing lens, the lens is thin and light in weight, has smaller pressure on the nose bridge after being worn, and is more suitable for being worn.
Description
Technical Field
The invention relates to the technical field of optical lenses, in particular to a 1.60-refractivity color-changing monomer material, a lens and a preparation method thereof.
Background
Color changing lenses, also known as "photosensitive lenses". According to the light color interconversion reversible reaction principle, the lens can quickly darken under the irradiation of light and ultraviolet rays, blocks strong light, absorbs the ultraviolet rays, and is neutral in visible light absorption; and when the lens returns to the dark place, the colorless and transparent state can be quickly recovered, and the transmittance of the lens is ensured. Therefore, the color-changing lens is suitable for being used indoors and outdoors simultaneously, and can prevent the damage of sunlight, ultraviolet light and glare to eyes.
The existing color-changing lenses can be divided into substrate color-changing lenses and film color-changing lenses. The substrate discolors by doping the discoloring agent in the monomer raw materials, and the whole lens is filled with the discoloring agent after being produced, so that the lens has the advantages of long discoloring time and high temperature resistance; the film layer color-changing lens utilizes a coating color-changing technology. The high-refractive index color-changing monomer on the market is few, and the main application of most high-refractive index color-changing lenses is the coating color-changing technology. Although the coating color change technology can be used for various resin lenses, there is a great problem: under the irradiation of ultraviolet rays, there is a significant delamination phenomenon.
Therefore, how to provide a high refractive index color-changing monomer material that can avoid the delamination phenomenon is a problem that needs to be solved by those skilled in the art.
Disclosure of Invention
In view of the above, the present invention provides a 1.60 refractive index color-changing monomer material, a lens and a preparation method thereof. The invention aims to solve the problem of delamination of a high-refractive-index photochromic lens under ultraviolet irradiation.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a 1.60-refractivity color-changing monomer material which comprises the following components in parts by weight:
30-50 parts of ethoxylated bisphenol fluorene acrylate, 5-10 parts of dibenzyl maleate, 25-30 parts of ethoxylated bisphenol A acrylate, 18-25 parts of benzene series and 2-5 parts of antioxidant.
Further, the ethoxylated bisphenol fluorene acrylate is ethoxylated bisphenol fluorene diacrylate or ethoxylated bisphenol fluorene dimethacrylate.
Further, the ethoxylated bisphenol A acrylate is ethoxylated bisphenol A diacrylate or ethoxylated bisphenol A dimethacrylate.
Further, the benzene series is styrene or alpha-methyl styrene.
Further, the antioxidant is antioxidant 1010, antioxidant 168 or antioxidant 619.
The invention provides a preparation method of a lens containing the 1.60-refractivity color-changing monomer material, which comprises the following steps:
mixing the 1.60-refractivity color-changing monomer material, the color-changing liquid, the UV powder and the azo initiator to obtain a mixture, and sequentially degassing, filling, curing, releasing, cleaning, secondary curing, hardening and coating the mixture to obtain the lens.
Further, the mass of the color changing liquid is 2-3% of that of the color changing monomer material with the refractive index of 1.60;
the mass of the uv powder is 0.1-0.5% of that of the photochromic monomer material with the refractive index of 1.60;
the mass of the azo initiator is 0.8-1.2% of that of the 1.60-refractivity color-changing monomer material.
Further, the azo initiator is azobisisoheptonitrile; the color-changing liquid is tea color-changing liquid or gray color-changing liquid.
Furthermore, the temperature of the curing and the secondary curing are independent from each other at 30-95 ℃ for 15-30 h.
The invention provides a lens prepared by the preparation method.
According to the technical scheme, compared with the prior art, the invention has the following beneficial effects:
the lens made of the 1.60-refractivity color-changing monomer material prepared by the invention is qualified in quality, high in color-changing speed and long in service life, and compared with a 1.56-refractivity color-changing lens, the lens is thin and light in weight, has smaller pressure on the nose bridge after being worn, and is more suitable for being worn; according to the lens preparation process provided by the invention, the photosensitive particles are mixed with the lens material without plating a layer of color-changing material on the surface of the lens, so that the prepared lens is full and mellow in color-changing effect, and cannot be layered under ultraviolet irradiation.
Detailed Description
The invention provides a 1.60-refractivity color-changing monomer material which comprises the following components in parts by weight:
30-50 parts of ethoxylated bisphenol fluorene acrylate, 5-10 parts of dibenzyl maleate, 25-30 parts of ethoxylated bisphenol A acrylate, 18-25 parts of benzene series and 2-5 parts of antioxidant.
In the present invention, the components in parts by weight are preferably: 34-46 parts of ethoxylated bisphenol fluorene acrylate, 6-9 parts of dibenzyl maleate, 26-29 parts of ethoxylated bisphenol A acrylate, 20-24 parts of benzene series and 3-5 parts of antioxidant.
In the present invention, the components in parts by weight are further preferably: 37-41 parts of ethoxylated bisphenol fluorene acrylate, 7-8 parts of dibenzyl maleate, 27-28 parts of ethoxylated bisphenol A acrylate, 22-23 parts of benzene series and 4 parts of antioxidant.
In the invention, the ethoxylated bisphenol fluorene acrylate is ethoxylated bisphenol fluorene diacrylate or ethoxylated bisphenol fluorene dimethacrylate, preferably ethoxylated bisphenol fluorene diacrylate.
In the present invention, the ethoxylated bisphenol a acrylate is an ethoxylated bisphenol a diacrylate or an ethoxylated bisphenol a dimethacrylate, preferably an ethoxylated bisphenol a diacrylate.
In the present invention, the benzene series is styrene or alpha-methylstyrene, preferably styrene.
In the present invention, the antioxidant is antioxidant 1010, antioxidant 168 or antioxidant 619, preferably antioxidant 1010 or antioxidant 168, and more preferably antioxidant 168.
The invention provides a preparation method of a lens containing the 1.60-refractivity color-changing monomer material, which comprises the following steps:
mixing the 1.60-refractivity color-changing monomer material, the color-changing liquid, the UV powder and the azo initiator to obtain a mixture, and sequentially degassing, filling, curing, releasing, cleaning, secondary curing, hardening and coating the mixture to obtain the lens.
In the present invention, degassing, filling, releasing, cleaning, hardening and plating are all processes that are conventional in the art.
In the invention, the mass of the color changing liquid is 2-3% of that of the color changing monomer material with the refractive index of 1.60, and is preferably 2%;
the mass of the UV powder is 0.1-0.5% of that of the color-changing monomer material with the refractive index of 1.60, preferably 0.2-0.4%, and further preferably 0.3%;
the mass of the azo initiator is 0.8-1.2% of that of the 1.60-refractivity color-changing monomer material, preferably 0.9-1.1%, and more preferably 1.0%.
In the present invention, the azo initiator is azobisisoheptonitrile; the color changing liquid is tea color changing liquid or gray color changing liquid, and is preferably tea color changing liquid.
In the invention, the temperature of the curing and the secondary curing is independent from 30-95 ℃, preferably 40-80 ℃, and further preferably 50-60 ℃; the time is independently 15-30 h, preferably 16-28 h, and more preferably 20-25 h.
The technical solutions in the embodiments of the present invention will be described clearly and completely below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
At room temperature, 32 parts of ethoxylated bisphenol fluorene diacrylate, 7 parts of dibenzyl maleate, 26 parts of ethoxylated bisphenol A diacrylate, 20 parts of styrene and 3 parts of antioxidant 1010 are mixed and stirred for 30min to obtain a photochromic monomer material with the refractive index of 1.60;
mixing the 1.60-refractivity color-changing monomer material, the tea color-changing liquid, the UV powder and the azobisisoheptonitrile to obtain a mixture, and sequentially degassing, filling, curing, releasing, cleaning, secondary curing, hardening and coating the mixture to obtain the lens. Wherein, the mass of the brown color-changing liquid is 2 percent of the mass of the 1.60 refractive index color-changing monomer material, the mass of the UV powder is 0.3 percent of the mass of the 1.60 refractive index color-changing monomer material, and the mass of the azodiisoheptonitrile is 0.8 percent of the mass of the 1.60 refractive index color-changing monomer material.
In this example, the curing and the secondary curing were both carried out at 50 ℃ for 25 hours.
Example 2
At room temperature, 45 parts of ethoxylated bisphenol fluorene diacrylate, 8 parts of dibenzyl maleate, 28 parts of ethoxylated bisphenol A diacrylate, 18 parts of styrene and 4 parts of antioxidant 168 are mixed and stirred for 30min to obtain a photochromic monomer material with the refractive index of 1.60;
mixing the 1.60-refractivity color-changing monomer material, the gray color-changing liquid, the UV powder and the azobisisoheptonitrile to obtain a mixture, and sequentially degassing, filling, curing, releasing, cleaning, secondarily curing, hardening and coating the mixture to obtain the lens. Wherein, the mass of the gray color-changing liquid is 3 percent of the mass of the 1.60 refractive index color-changing monomer material, the mass of the UV powder is 0.4 percent of the mass of the 1.60 refractive index color-changing monomer material, and the mass of the azodiisoheptonitrile is 0.9 percent of the mass of the 1.60 refractive index color-changing monomer material.
In this example, the curing and the secondary curing were carried out at 70 ℃ for 22 hours.
Example 3
At room temperature, mixing and stirring 40 parts of ethoxylated bisphenol fluorene diacrylate, 9 parts of dibenzyl maleate, 30 parts of ethoxylated bisphenol A diacrylate, 22 parts of styrene and 5 parts of antioxidant 619 for 30min to obtain a photochromic monomer material with the refractive index of 1.60;
mixing the 1.60-refractivity color-changing monomer material, the tea color-changing liquid, the UV powder and the azobisisoheptonitrile to obtain a mixture, and sequentially degassing, filling, curing, releasing, cleaning, secondary curing, hardening and coating the mixture to obtain the lens. Wherein the mass of the tea color changing liquid is 2.5 percent of the mass of the 1.60 refractive index color changing monomer material, the mass of the UV powder is 0.5 percent of the mass of the 1.60 refractive index color changing monomer material, and the mass of the azodiisoheptanonitrile is 1.0 percent of the mass of the 1.60 refractive index color changing monomer material.
In this example, the curing and the secondary curing were carried out at 80 ℃ for 20 hours.
Example 4
At room temperature, 32 parts of ethoxylated bisphenol fluorene dimethacrylate, 7 parts of dibenzyl maleate, 26 parts of ethoxylated bisphenol A diacrylate, 20 parts of alpha-methyl styrene and 3 parts of antioxidant 1010 are mixed and stirred for 30min to obtain a color-changing monomer material with the refractive index of 1.60;
mixing the 1.60-refractivity color-changing monomer material, the tea color-changing liquid, the UV powder and the azobisisoheptonitrile to obtain a mixture, and sequentially degassing, filling, curing, releasing, cleaning, secondary curing, hardening and coating the mixture to obtain the lens. Wherein, the mass of the brown color-changing liquid is 2 percent of the mass of the 1.60 refractive index color-changing monomer material, the mass of the UV powder is 0.3 percent of the mass of the 1.60 refractive index color-changing monomer material, and the mass of the azodiisoheptonitrile is 1.1 percent of the mass of the 1.60 refractive index color-changing monomer material.
In this example, the curing and the secondary curing were both carried out at 50 ℃ for 25 hours.
Example 5
At room temperature, 45 parts of ethoxylated bisphenol fluorene dimethacrylate, 8 parts of dibenzyl maleate, 28 parts of ethoxylated bisphenol A diacrylate, 18 parts of alpha-methyl styrene and 4 parts of antioxidant 168 are mixed and stirred for 30min to obtain a color-changing monomer material with the refractive index of 1.60;
mixing the 1.60-refractivity color-changing monomer material, the gray color-changing liquid, the UV powder and the azobisisoheptonitrile to obtain a mixture, and sequentially degassing, filling, curing, releasing, cleaning, secondarily curing, hardening and coating the mixture to obtain the lens. Wherein, the mass of the gray color-changing liquid is 3 percent of the mass of the 1.60 refractive index color-changing monomer material, the mass of the UV powder is 0.4 percent of the mass of the 1.60 refractive index color-changing monomer material, and the mass of the azodiisoheptonitrile is 1.2 percent of the mass of the 1.60 refractive index color-changing monomer material.
In this example, the curing and the secondary curing were carried out at 70 ℃ for 22 hours.
Performance test
And (3) ageing resistance: the lenses prepared in examples 1-5 were placed in a UV weathering chamber at 80 ℃ for 72 h. The results show that: none of the base colors of the lenses prepared in examples 1-5 changed, indicating that the lenses prepared in accordance with the present invention meet the national requirements.
Impact resistance: the concave surface of the lens prepared in examples 1 to 5 was impacted by freely dropping a steel ball 16mm in diameter and 16g in weight from a height of 1.3m of the ball drop tester. The results show that: none of the concave surfaces of the lenses prepared in examples 1-5 cracked and no debris was generated, indicating that the lenses prepared in accordance with the present invention had excellent impact resistance.
Scratch resistance: the light transmittance A of the lenses prepared in examples 1 to 5 was measured 1 After the lens prepared in examples 1 to 5 was wiped with No. 1000 steel wool under a load of 1kg repeatedly 10 times, the lens was cleaned and the light transmittance A was measured again 2 Calculating A 2 /A 1 The results are shown in table 1:
table 1: scratch resistance test results for lenses prepared in examples 1-5
| Example 1 | Example 2 | Example 3 | Example 4 | Example 5 | |
| A 2 /A 1 | 89.6％ | 89.2％ | 90.3％ | 88.9％ | 90.1％ |
As can be seen from Table 1, the percent reduction in light transmission for the lenses prepared in examples 1-5 is small, indicating that the lenses prepared in accordance with the present invention have excellent scratch resistance.
In the present specification, the embodiments are described in a progressive manner, each embodiment focuses on differences from other embodiments, and the same and similar parts among the embodiments are referred to each other.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (10)
1. The 1.60-refractivity color-changing monomer material is characterized by comprising the following components in parts by weight:
30-50 parts of ethoxylated bisphenol fluorene acrylate, 5-10 parts of dibenzyl maleate, 25-30 parts of ethoxylated bisphenol A acrylate, 18-25 parts of benzene series and 2-5 parts of antioxidant.
2. A 1.60 index of refraction color changing monomer material of claim 1, wherein the ethoxylated bisphenol fluorene acrylate is ethoxylated bisphenol fluorene diacrylate or ethoxylated bisphenol fluorene dimethacrylate.
3. A refractive index color changing monomer material of claim 1.60, wherein the ethoxylated bisphenol a acrylate is ethoxylated bisphenol a diacrylate or ethoxylated bisphenol a dimethacrylate.
4. A 1.60 index of refraction color changing monomer material of claim 2 or 3, wherein the benzene series is styrene or alpha-methyl styrene.
5. The 1.60-refractivity color-changing monomer material according to claim 4, wherein the antioxidant is antioxidant 1010, antioxidant 168 or antioxidant 619.
6. A method for preparing a lens comprising the 1.60 refractivity color-changing monomer material according to any one of claims 1 to 5, wherein the method comprises the following steps:
mixing the 1.60-refractivity color-changing monomer material, the color-changing liquid, the UV powder and the azo initiator to obtain a mixture, and sequentially degassing, filling, curing, releasing, cleaning, secondary curing, hardening and coating the mixture to obtain the lens.
7. The preparation method according to claim 6, wherein the mass of the color-changing liquid is 2-3% of that of the color-changing monomer material with the refractive index of 1.60;
the mass of the UV powder is 0.1-0.5% of that of the photochromic monomer material with the refractive index of 1.60;
the mass of the azo initiator is 0.8-1.2% of that of the 1.60 refractive index color-changing monomer material.
8. The production method according to claim 6 or 7, characterized in that the azo initiator is azobisisoheptonitrile; the color-changing liquid is tea color-changing liquid or gray color-changing liquid.
9. The method according to claim 8, wherein the curing temperature and the secondary curing temperature are 30 to 95 ℃ and 15 to 30 hours, respectively.
10. A lens produced by the production method according to any one of claims 6 to 9.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202210955118.4A CN115109186A (en) | 2022-08-10 | 2022-08-10 | 1.60-refractive-index color-changing monomer material, lens and preparation method thereof |
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| CN202210955118.4A CN115109186A (en) | 2022-08-10 | 2022-08-10 | 1.60-refractive-index color-changing monomer material, lens and preparation method thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2024247799A1 (en) * | 2023-05-29 | 2024-12-05 | 株式会社トクヤマ | Curable composition, cured body, optical article, lens, and eyeglasses |
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| CN111349188A (en) * | 2020-05-08 | 2020-06-30 | 江苏全真光学科技股份有限公司 | Photochromic substrate material, photochromic lens and preparation method thereof |
| WO2021169033A1 (en) * | 2020-02-28 | 2021-09-02 | 江苏康耐特光学有限公司 | Photochromic resin lens with refractive index of 1.50 and preparation method therefor |
| CN113845619A (en) * | 2021-09-30 | 2021-12-28 | 山东鲁源化工科技有限公司 | High-refractive-index color-changing monomer and preparation method and application thereof |
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- 2022-08-10 CN CN202210955118.4A patent/CN115109186A/en active Pending
Patent Citations (4)
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| CN105452310A (en) * | 2013-08-08 | 2016-03-30 | 可奥熙搜路司有限公司 | Polymerizable composition for high-refractive optical material and method for preparing high-refractive optical material |
| WO2021169033A1 (en) * | 2020-02-28 | 2021-09-02 | 江苏康耐特光学有限公司 | Photochromic resin lens with refractive index of 1.50 and preparation method therefor |
| CN111349188A (en) * | 2020-05-08 | 2020-06-30 | 江苏全真光学科技股份有限公司 | Photochromic substrate material, photochromic lens and preparation method thereof |
| CN113845619A (en) * | 2021-09-30 | 2021-12-28 | 山东鲁源化工科技有限公司 | High-refractive-index color-changing monomer and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2024247799A1 (en) * | 2023-05-29 | 2024-12-05 | 株式会社トクヤマ | Curable composition, cured body, optical article, lens, and eyeglasses |
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