CN113845619A - High-refractive-index color-changing monomer and preparation method and application thereof - Google Patents
High-refractive-index color-changing monomer and preparation method and application thereof Download PDFInfo
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- 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
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- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
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Abstract
The invention discloses a high-refractive-index color-changing monomer and a preparation method and application thereof, wherein the high-refractive-index color-changing monomer comprises the following raw materials in parts by weight: (1) monomer mixture: 30-50% of acrylate monomer, 5-10% of dibenzyl maleate, 25-30% of cross-linking agent, 18-25% of vinyl monomer and 2-5% of antioxidant; (2) color-changing monomer mixture: 95% -97% of a monomer mixture; 2% -3% of color-changing liquid; 0.5 to 2 percent of initiator. The acrylic ester monomer in the high-refractive-index color-changing monomer improves the refractive index of optical resin, and the ethoxylated bisphenol fluorene diacrylate or the ethoxylated bisphenol fluorene dimethacrylate is selected because the ethoxylated group has a synergistic effect on photochromic effect, the chain segment of the ethoxylated group is soft, so that large steric hindrance is provided for the color-changing group, the color-changing strength is better, the light transmittance after color changing is lower, dibenzyl maleate is introduced to increase the plasticity of the optical resin monomer, styrene compounds are introduced to reduce the overall viscosity of the monomer, the operation of lens synthesis is facilitated, and the impact resistance and the wear resistance of the optical resin are improved.
Description
Technical Field
The invention belongs to the technical field of color-changing glasses, and particularly relates to a high-refractive-index color-changing monomer and a preparation method and application 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 lens can be divided into a substrate color-changing lens and a film color-changing lens. The basic change is that the color-changing agent is mixed in the monomer raw material, and the whole lens is filled with the color-changing agent after being produced, so that the lens has the advantages of long color-changing time and high temperature resistance; the film layer color changing lens is a coating color changing technology. In the market, the high-refractive-index color-changing lens mainly uses a coating color-changing technology because the high-refractive-index color-changing monomer is less. Although the coating discoloration technique can be used for various resin lenses, a great problem is that the coating is obviously layered under the irradiation of ultraviolet rays. The 1.56-index color-changing lens in the market is the most widely used color-changing lens with the highest yield and sales volume. But since the 1.60 index color-changing monomer is less on the market, the method is less for producing the 1.60 index color-changing lens.
Disclosure of Invention
The invention aims to provide a high-refractivity color-changing monomer and a preparation method of color-changing glasses, which can be used for well manufacturing a high-refractivity color-changing lens and solving the problem that the lens is layered under ultraviolet irradiation.
In order to achieve the purpose, the invention provides a high-refractive-index color-changing monomer which comprises the following raw materials in parts by weight:
(1) monomer mixture:
30 to 50 percent of acrylate monomer
5 to 10 percent of maleic acid dibenzyl ester
25 to 30 percent of cross-linking agent
18% -25% of vinyl monomer;
2 to 5 percent of antioxidant;
(2) color-changing monomer mixture:
95% -97% of a monomer mixture;
2% -3% of color-changing liquid;
0.5 to 2 percent of initiator.
As a preferable technical scheme of the invention, the acrylate monomer is ethoxylated bisphenol fluorene diacrylate or ethoxylated bisphenol fluorene dimethacrylate.
In a preferred embodiment of the present invention, the crosslinking agent is ethoxylated bisphenol a diacrylate or ethoxylated bisphenol a dimethacrylate, and the vinyl monomer is styrene or α -methylstyrene.
As a preferable technical scheme of the invention, the initiator is an azo initiator.
In a preferred embodiment of the present invention, the color-changing liquid contains an organic solvent for a spiropyran-based or spirooxazine-based photochromic compound.
In addition, the invention also provides a high-refractive-index color-changing monomer, which comprises the following steps: s1:
at normal temperature, uniformly mixing an acrylate monomer and a cross-linking agent;
s2: adding dibenzyl maleate, vinyl monomer and antioxidant into the mixed solution prepared in the step S1 in sequence, and fully stirring to obtain a monomer mixture;
s3: and adding the color-changing liquid and the initiator into the monomer mixture, and stirring for 1h to obtain the color-changing monomer mixture.
In addition, the invention also provides application of the high-refractive-index color-changing monomer, which is applied to
The preparation method of the color-changing lens comprises the following steps:
s4: adding UV powder into the color-changing monomer prepared according to the method of claim 6, and uniformly stirring;
s5: discharging bubbles from the mixture obtained in step S4, pouring into a mold, and placing into a mold
In the chemical furnace, the curing reaction was carried out according to the following procedure:
and S6, carrying out the procedures of releasing, cleaning, secondary curing, hardening, coating and the like on the lens after the curing reaction of the S5 is finished to prepare the color-changing lens.
The invention has the beneficial effects that: the acrylic ester monomer in the high-refractive-index color-changing monomer improves the refractive index of optical resin, and the ethoxylated bisphenol fluorene diacrylate or the ethoxylated bisphenol fluorene dimethacrylate is selected because the ethoxylated group has a synergistic effect on photochromic effect, the chain segment of the ethoxylated group is soft, so that large steric hindrance is provided for the color-changing group, the color-changing strength is better, the light transmittance after color changing is lower, dibenzyl maleate is introduced to increase the plasticity of the optical resin monomer, styrene compounds are introduced to reduce the overall viscosity of the monomer, the operation of lens synthesis is facilitated, and the impact resistance and the wear resistance of the optical resin are improved.
The photochromic lens of the invention abandons the process of plating a layer of photochromic material on the surface of the lens, and the photosensitive particles are mixed with the lens material, so that the prepared lens has qualified quality, high photochromic speed, long service life, better and full photochromic effect and mellowness, and the problem of layering of the lens under the irradiation of ultraviolet rays is solved.
Detailed Description
The present invention will be further described with reference to specific examples, but the present invention is not limited to these examples.
Example 1
A high-refractive-index color-changing monomer comprises the following raw materials in parts by weight:
(1) monomer mixture:
ethoxylated bisphenol fluorene diacrylate 40%
5 percent of dibenzyl maleate
Ethoxylated bisphenol A diacrylate 30%
22% of styrene;
3% of 2, 6-di-tert-butyl-4-methylphenol;
(2) color-changing monomer mixture:
95.5% of a monomer mixture;
3% of color-changing liquid;
azodiisobutyronitrile 1.5%.
Wherein the color-changing liquid is methyl methacrylate solution containing 3 percent of 1- (2-ethoxyl) -3, 3-dimethyl indoline-6' -nitro benzo spiropyran.
A high refractive index color-changing monomer comprising the steps of:
s1: at normal temperature, uniformly mixing ethoxylated bisphenol fluorene diacrylate and ethoxylated bisphenol A diacrylate;
s2: adding dibenzyl maleate, styrene and 2, 6-ditert-butyl-4-methylphenol into the mixed solution prepared in the step S1 in sequence, and fully stirring to obtain a monomer mixture;
s3: and adding the color-changing liquid and the azobisisobutyronitrile into the monomer mixture, and stirring for 1h to obtain the color-changing monomer mixture.
The preparation method of the color-changing lens comprises the following steps:
s4: adding 0.4% of UV powder into the color-changing monomer prepared in the S3, and uniformly stirring;
s5: discharging bubbles in the mixture prepared in the step S4, pouring the mixture into a mold, putting the mold into a curing furnace, and carrying out curing reaction according to the following procedures:
and S6, carrying out the procedures of releasing, cleaning, secondary curing, hardening, coating and the like on the lens after the curing reaction of the S5 is finished to prepare the color-changing lens.
Example 2
A high-refractive-index color-changing monomer comprises the following raw materials in parts by weight:
(1) monomer mixture:
ethoxylated bisphenol fluorene dimethacrylate 40%
5 percent of dibenzyl maleate
Ethoxylated bisphenol A dimethacrylate 30%
22% of alpha-methyl styrene;
3% of 2, 6-di-tert-butyl-4-methylphenol;
(2) color-changing monomer mixture:
95.5% of a monomer mixture;
3% of color-changing liquid;
azodiisobutyronitrile 1.5%.
Wherein the color-changing liquid is methyl methacrylate solution containing 3 percent of 1- (2-ethoxyl) -3, 3-dimethyl indoline-6' -nitro benzo spiropyran.
A high refractive index color-changing monomer comprising the steps of:
s1: at normal temperature, uniformly mixing ethoxylated bisphenol fluorene dimethacrylate and ethoxylated bisphenol A dimethacrylate;
s2: adding dibenzyl maleate, alpha-methyl styrene and 2, 6-ditert-butyl-4-methylphenol into the mixed solution prepared in the step S1 in sequence, and fully stirring to obtain a monomer mixture;
s3: and adding the color-changing liquid and the azobisisobutyronitrile into the monomer mixture, and stirring for 1h to obtain the color-changing monomer mixture.
The preparation method of the color-changing lens comprises the following steps:
s4: adding 0.4% of UV powder into the color-changing monomer prepared in the S3, and uniformly stirring;
s5: discharging bubbles in the mixture prepared in the step S4, pouring the mixture into a mold, putting the mold into a curing furnace, and carrying out curing reaction according to the following procedures:
and S6, carrying out the procedures of releasing, cleaning, secondary curing, hardening, coating and the like on the lens after the curing reaction of the S5 is finished to prepare the color-changing lens.
Example 3
A high-refractive-index color-changing monomer comprises the following raw materials in parts by weight:
(1) monomer mixture:
20 percent of ethoxylated bisphenol fluorene dimethacrylate
20 percent of ethoxylated bisphenol fluorene diacrylate
5 percent of dibenzyl maleate
Ethoxylated bisphenol A dimethacrylate 15%
Ethoxylated bisphenol A diacrylate 15%
22% of alpha-methyl styrene;
3% of 2, 6-di-tert-butyl-4-methylphenol;
(2) color-changing monomer mixture:
95.5% of a monomer mixture;
3% of color-changing liquid;
azodiisobutyronitrile 1.5%.
Wherein the color-changing liquid is methyl methacrylate solution containing 3 percent of 1- (2-ethoxyl) -3, 3-dimethyl indoline-6' -nitro benzo spiropyran.
A high refractive index color-changing monomer comprising the steps of:
s1: at normal temperature, uniformly mixing ethoxylated bisphenol fluorene dimethacrylate and ethoxylated bisphenol A dimethacrylate;
s2: adding dibenzyl maleate, alpha-methyl styrene and 2, 6-ditert-butyl-4-methylphenol into the mixed solution prepared in the step S1 in sequence, and fully stirring to obtain a monomer mixture;
s3: and adding the color-changing liquid and the azobisisobutyronitrile into the monomer mixture, and stirring for 1h to obtain the color-changing monomer mixture.
The preparation method of the color-changing lens comprises the following steps:
s4: adding 0.4% of UV powder into the color-changing monomer prepared in the S3, and uniformly stirring;
s5: discharging bubbles in the mixture prepared in the step S4, pouring the mixture into a mold, putting the mold into a curing furnace, and carrying out curing reaction according to the following procedures:
and S6, carrying out the procedures of releasing, cleaning, secondary curing, hardening, coating and the like on the lens after the curing reaction of the S5 is finished to prepare the color-changing lens.
Example 4
A high-refractive-index color-changing monomer comprises the following raw materials in parts by weight:
(1) monomer mixture:
ethoxylated bisphenol fluorene dimethacrylate 50%
5 percent of dibenzyl maleate
Ethoxylated bisphenol A dimethacrylate 25%
18% of alpha-methyl styrene;
2% of 2, 6-di-tert-butyl-4-methylphenol;
(2) color-changing monomer mixture:
95.5% of a monomer mixture;
3% of color-changing liquid;
azodiisobutyronitrile 1.5%.
Wherein the color-changing liquid is methyl methacrylate solution containing 3 percent of 1- (2-ethoxyl) -3, 3-dimethyl indoline-6' -nitro benzo spiropyran.
A high refractive index color-changing monomer comprising the steps of:
s1: at normal temperature, uniformly mixing ethoxylated bisphenol fluorene dimethacrylate and ethoxylated bisphenol A dimethacrylate;
s2: adding dibenzyl maleate, alpha-methyl styrene and 2, 6-ditert-butyl-4-methylphenol into the mixed solution prepared in the step S1 in sequence, and fully stirring to obtain a monomer mixture;
s3: and adding the color-changing liquid and the azobisisobutyronitrile into the monomer mixture, and stirring for 1h to obtain the color-changing monomer mixture.
The preparation method of the color-changing lens comprises the following steps:
s4: adding 0.4% of UV powder into the color-changing monomer prepared in the S3, and uniformly stirring;
s5: discharging bubbles in the mixture prepared in the step S4, pouring the mixture into a mold, putting the mold into a curing furnace, and carrying out curing reaction according to the following procedures:
and S6, carrying out the procedures of releasing, cleaning, secondary curing, hardening, coating and the like on the lens after the curing reaction of the S5 is finished to prepare the color-changing lens.
Comparative example 1
Prepared according to the method of example 2 of application No. 2009100477236:
the formula (weight) is as follows:
the preparation method comprises the following steps: the composition is fully stirred and uniformly mixed, then is filtered by a 0.5 micron filter and poured into a glass mould prepared in advance, and the poured mould is put into an air oven to carry out polymerization reaction according to the following heating procedure:
after heating and polymerization, the mould is removed from the glass at 60 ℃ to obtain the high-refractive-index resin color-changing spectacle lens, and then the resin color-changing spectacle lens is coated with a hard coating on the surface and plated with a color-reducing and reflecting film in vacuum to obtain a marketable product.
Comparative example 2
Prepared according to the method of example 8 of application No. 2018115254013
Mixing and stirring 46Kg of brominated epoxy acrylate, 20Kg of epoxy resin, 10Kg of dibenzyl maleate, 14Kg of styrene, 1.5Kg of dodecyl mercaptan and 0.7Kg of trioctyl phosphate uniformly, adding 0.2Kg of initiator azobisisoheptonitrile, degassing, injecting, putting into an oven, heating to 40 ℃ within 1.5 h; the temperature is increased from 40 ℃ to 100 ℃ within 4 h; then preserving the heat for 8 hours; and then raising the temperature from 100 ℃ to 150 ℃ within 2.5h, preserving the temperature for 3h, and then reducing the temperature from 150 ℃ to room temperature within 2.5h to obtain the high-refractive-index optical resin monomer.
From the above, the plant growth agent of the invention can effectively promote the growth of tobacco seedlings, improve the plant height, increase the length and width of tobacco leaves, improve the yield and quality of the tobacco leaves and improve the economic benefit of tobacco leaf planting.
The physical properties of the prepared photochromic lenses were measured by the following methods, and the results thereof are shown in table 1.
1) Refractive index and abbe number: measured using an Abbe refractometer of the model DR-M4 from Atago;
2) specific gravity: measured according to the displacement in water method using an analytical balance;
3) demolding property: the composition is thermally cured when preparing a color-changing lens and represents "O" or "X" according to the breakage of the lens or the mold when the color-changing lens and the mold are separated at 70 ℃. "O" indicates that the lens or the mold is not broken at all or 1 in the separation process of 100 color-changing lenses and molds. "X" represents the case where more than 4 lenses or molds are broken during the separation of 100 color changing lenses and molds;
4) transparency: placing 100 lenses under USHIOUSH-10D mercury arc lamp, and observing with naked eye, wherein the turbidity of the color-changing lens below 3 is represented by "O", and the turbidity of the color-changing lens above 3 is represented by "X";
5) thermal stabilizer: the cured photochromic lens was maintained at 100 ℃ for 10 hours, and when the APHA value in the color change measurement was 2 or more, no change was represented by "O", and when the APHA value was 2 or more, a change was represented by "X".
6) Light resistance: an accelerated weathering tester (AccelerlatedWeatheringtester) of the Q-Lab corporation QUV/SE model was used. In the QUV test, a flat lens having a thickness of 1.2mm was irradiated with UVA-340(340nm), a light quantity of 0.76W/m2, 4-hour BPT (blank Panel temperature) (60 ℃), and condensation (condensation) for 4 hours at 50 ℃ for 8 hours, and then, when the APHA value in the color change measurement was 3 or more, no change was represented by "O", and when the APHA value was 3 or more, a change was represented by "X".
7) Discoloration speed and fading speed: and (3) irradiating the color-changing lens under visible light, and recording the time when the lens changes color to a stable state and the time for recovering the color-changing lens after the light source is removed.
TABLE 1 Properties of color changing lens
| Optical characteristics | Example 1 | Example 2 | Example 3 | Example 4 | Comparative example 1 | Comparative example 2 |
| Refractive index (nE,20 ℃ C.) | 1.617 | 1.619 | 1.620 | 1.616 | 1.619 | 1.592 |
| Abbe number (ud,20 ℃ C.) | 30.2 | 30.1 | 30.5 | 30.4 | 29.8 | 29.9 |
| Specific gravity of | 1.197 | 1.198 | 1.198 | 1.200 | 1.203 | 1.199 |
| Releasability from mold | 0 | 0 | 0 | 0 | 0 | 0 |
| Heat stabilizer | 0 | 0 | 0 | 0 | 0 | 0 |
| Light resistance | 0 | 0 | 0 | 0 | 0 | 0 |
| Speed of color change(s) | 58 | 59 | 56 | 59 | 63 | 61 |
| Fading speed(s) | 165 | 171 | 167 | 169 | 183 | 178 |
As can be seen from the table above, the high-refractive-index color-changing monomer disclosed by the invention is high in refractive index, high in color-changing speed, low in specific gravity and high in wearing comfort.
Although the present application has been described with reference to a few embodiments, it should be understood that various changes, substitutions and alterations can be made herein without departing from the spirit and scope of the application as defined by the appended claims.
Claims (7)
1. The high-refractive-index color-changing monomer is characterized by comprising the following raw materials in parts by weight:
(1) monomer mixture:
30 to 50 percent of acrylate monomer
5 to 10 percent of maleic acid dibenzyl ester
25 to 30 percent of cross-linking agent
18% -25% of vinyl monomer;
2 to 5 percent of antioxidant;
(2) color-changing monomer mixture:
95% -97% of a monomer mixture;
2% -3% of color-changing liquid;
0.5 to 2 percent of initiator.
2. A high index of refraction color shifting monomer according to claim 1, wherein: the acrylate monomer is ethoxylated bisphenol fluorene diacrylate or ethoxylated bisphenol fluorene dimethacrylate.
3. A high index of refraction color shifting monomer according to claim 1, wherein: the cross-linking agent is ethoxylated bisphenol A diacrylate or ethoxylated bisphenol A dimethacrylate, and the vinyl monomer is styrene or alpha-methyl styrene.
4. A high index of refraction color shifting monomer according to claim 1, wherein: the initiator is an azo initiator.
5. A high index of refraction color shifting monomer according to claim 1, wherein: the color-changing liquid contains an organic solvent of a spiropyran or spirooxazine photochromic compound.
6. A method for preparing the high refractive index color-changing monomer according to any one of claims 1 to 5, comprising the steps of:
s1: at normal temperature, uniformly mixing an acrylate monomer and a cross-linking agent;
s2: adding dibenzyl maleate, vinyl monomer and antioxidant into the mixed solution prepared in the step S1 in sequence, and fully stirring to obtain a monomer mixture;
s3: and adding the color-changing liquid and the initiator into the monomer mixture, and stirring for 1h to obtain the color-changing monomer mixture.
7. The application of the high-refraction color-changing monomer is characterized in that the high-refraction color-changing monomer is applied to a color-changing lens, and the preparation method of the color-changing lens comprises the following steps:
s4: adding UV powder into the color-changing monomer prepared according to the method of claim 6, and uniformly stirring;
s5: discharging bubbles in the mixture prepared in the step S4, pouring the mixture into a mold, putting the mold into a curing furnace, and carrying out curing reaction according to the following procedures:
and S6, carrying out the procedures of releasing, cleaning, secondary curing, hardening, coating and the like on the lens after the curing reaction of the S5 is finished to prepare the color-changing lens.
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| CN115109186A (en) * | 2022-08-10 | 2022-09-27 | 山东鲁源化工科技有限公司 | 1.60-refractive-index color-changing monomer material, lens and preparation method thereof |
| CN117551232A (en) * | 2023-11-16 | 2024-02-13 | 苏州奈膜凯新材料有限公司 | A method for synthesizing high refractive index polymer resin |
| 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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