CN108467361B - Quinophthalone compound, preparation method thereof and application of quinophthalone compound as light absorption material - Google Patents
Quinophthalone compound, preparation method thereof and application of quinophthalone compound as light absorption material Download PDFInfo
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- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
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Abstract
Quinophthalone compounds as shown in formula A, preparation method thereof and application thereof as light absorption material. The preparation method comprises the following steps: phthalic anhydride and 2-methyl-3-hydroxyquinoline are added into a reaction vessel according to the weight ratio of 1: 3-5, the solvent is 1, 3, 5-trichlorobenzene, the temperature is slowly raised to 150-. The application is that the quinophthalone compound shown in the formula A, the nano titanium dioxide with the core-shell structure and the ultraviolet absorbent are dispersed in the optical resin to form the blue light prevention resin material. The material has the performance of distinguishing and absorbing blue light of different wave bands, so that harmful blue light of medium and short wave bands keeps low transmittance, beneficial blue light of long wave bands and visible light of other wave bands keep high transmittance, the eyesight is protected, and the problem that ultraviolet light and blue light cause harm to eyes is solved well.
Description
Technical Field
The invention belongs to the technical field of light absorbers, and particularly relates to a light absorber with specific absorption wavelength in a 220-470nm spectral region and a preparation method thereof.
Background
It is well known that ultraviolet light can harm a person's eyes, but many people are unaware that blue light in visible light can also cause damage to the eyes. The blue light is used as part of visible light, has extremely high energy, the wavelength range is 400-500 nm, and with the wide popularization of electronic products such as computers, mobile phones and ipads, the unnatural light taking the blue light as a main body can cause irreversible damage to human eyes, and the problems of human eyes dryness, fatigue, lacrimation, myopia acceleration, yellow spot region diseases and the like are caused. Issuing an orange early warning according to the World Health Organization (WHO) 2009: the potential stealth threat of blue light to humans will far exceed the devastating effects of sudan red, melamine, SARS, etc., with at least 30000 people becoming blind each year from the radiation of blue light. The existing ultraviolet-proof optical materials are prepared by adding ultraviolet absorbers into optical resin, and the materials can usually effectively absorb purple light and ultraviolet rays, but cannot filter harmful blue light, namely, people can block the damage of the ultraviolet light when being irradiated by sunlight (in a bright environment); but cannot block a certain amount of blue light when returning indoors (dark environment); in addition, human eyes are insensitive to the visual objects and color discrimination of blue light in the range of 400-440nm, the wavelength of the light wave in the wavelength band is short, the energy is high, the damage to the eyes is large, and the optical lens keeps low transmittance for the blue light; the 470nm range of 440-. The coating process adopted abroad cannot distinguish the short, medium and long blue spectral regions, the total blue light effective rate can only reach 17%, or the visible light in other wave band parts is lost while the blue light is blocked, so that the visible light transmittance is low or the color is distorted. Therefore, it is necessary to develop an optical material that can effectively distinguish blue light in different wavelength bands, so that harmful blue light maintains low transmittance, and beneficial blue light and visible light in other wavelength bands maintain high transmittance.
Disclosure of Invention
The invention aims to provide a quinophthalone compound, the structure of which is shown as a formula A, and the quinophthalone compound can be used as a blue light prevention additive of an optical resin material, can be used in a synergistic effect with other ultraviolet absorbers to expand the blocking spectral range of the optical resin from an ultraviolet spectral region to a blue spectral region, has the performance of distinguishing and absorbing blue light of different wave bands, keeps low transmittance of harmful blue light of medium and short wave bands, keeps high transmittance of beneficial blue light of long wave band and visible light of other wave bands, has the total effective rate of the blue light of 53 percent, is beneficial to protecting eyesight, and better solves the problem that the ultraviolet light and the blue light cause damage to human eyes.
In order to achieve the purpose, the invention provides the following technical scheme:
a quinophthalone compound has a structure shown in formula A:
in another aspect, the present invention provides a method for preparing a quinophthalone compound as described above, comprising the steps of: adding phthalic anhydride and 2-methyl-3-hydroxyquinoline into a reaction vessel according to the weight ratio of 1: 3-5, adding 1, 3, 5-trichlorobenzene as a solvent, wherein the adding amount of the 1, 3, 5-trichlorobenzene is 0.7-1.3 times of the weight ratio of the 2-methyl-3-hydroxyquinoline, slowly heating to 150 ℃ and 200 ℃, keeping the temperature for 2-3 hours, carrying out condensation reaction, cooling the temperature to room temperature after the reaction is finished, filtering, washing solids with ethanol, and drying to obtain the product.
In a further aspect, the present invention provides the use of a compound as described above as a light absorbing material.
The above-mentioned application, preferably, the application is that the quinophthalone compound shown in formula A is dispersed in the optical resin as a light absorbing material to form a blue light-proof resin material.
The application is preferably to disperse the quinophthalone compound shown in the formula A, the nano titanium dioxide with the core-shell structure and the ultraviolet absorbent in the optical resin monomer to form the blue light prevention resin monomer.
In the above application, the weight ratio of the quinophthalone compound shown in the formula A, the nano titanium dioxide with the core-shell structure, the ultraviolet absorbent and the optical resin monomer is preferably (0.1-0.2): (0.5-3.0): (0.2-2.0): 100-150).
In the above-described application, the optical resin is preferably formed by polymerizing a polymer monomer, which is at least one of a diallyl dicarbonate monomer, a methacrylate monomer, a vinyl monomer, a urethane polymer monomer, an allyl monomer, and an epoxy polymer monomer.
For the above-mentioned applications, preferably, the blue-light-preventing resin monomer is polymerized to form the blue-light-preventing resin material.
In the above-mentioned application, preferably, the ultraviolet absorbent is at least one of UV-P, UV-326, UV-327, UV-328, UV-329, UV-360, UV-531 and UV-928.
In the application, preferably, the blue-light-proof resin material is composed of a quinophthalone compound shown in formula A, core-shell structure nano titanium dioxide, an ultraviolet absorbent UV-326 and polymethacrylate.
As mentioned above, preferably, the blue-light-proof resin material is composed of the quinophthalone compound shown in formula A, the nano titanium dioxide with the core-shell structure, the ultraviolet absorbent UV-326 and the polymethacrylate according to the weight ratio of 0.1: 1.5: 0.8: 100.
In the above application, preferably, the core of the core-shell structure nano titanium dioxide is titanium dioxide nano particles, and the particle size is 5-20 nm; the shell is a surfactant with the thickness of 2-5nm, and the surfactant is polyvinylpyrrolidone or sodium dodecyl benzene sulfonate.
The invention takes the quinophthalone compound shown in the formula A as the blue light absorber in the optical resin material, and the beneficial effects are shown in the following aspects:
1. the quinophthalone compound (formula A), the ultraviolet absorbent and the nano titanium dioxide are dispersed in the resin according to a proper proportion, so that the function of absorbing blue violet light can be cooperatively exerted, and particularly, the effect of absorbing medium and short wave blue light is obviously improved compared with the existing material, the absorption spectrum range is wide, and the absorption effect is good. Wherein, the transmittance of the ultraviolet spectrum region (220 plus 380nm) is less than or equal to 0.01 percent, the transmittance of the 400 plus 440nm blue light spectrum region is less than or equal to 6 percent, the transmittance of the 440 plus 470nm blue light spectrum region is less than or equal to 30 percent, and the transmittance of the 470 plus 500nm blue light spectrum region is more than or equal to 65 percent, which is beneficial to protecting the eyesight and better solves the problem of the damage of ultraviolet light and blue light to the eyes.
2. The addition amount of the quinophthalone compound in the optical resin material is less (less than 0.2 wt%), and due to the addition of the quinophthalone, the amount of other ultraviolet absorbers is greatly lower than the conventional amount, so that the influence of the ultraviolet absorbers on the light transmittance of the optical resin is reduced. The material has high transparency, and the transmittance of the visible light spectrum region above 500nm is more than or equal to 86%.
3. The quinophthalone compound shown in the formula A forms a stable hydrogen bond in molecules, as shown in the formula (C), the molecular structure is stable, and the optical resin material prepared from the quinophthalone compound has high thermal stability (the thermal stability is more than or equal to 250 ℃).
Drawings
FIG. 1 is a graph comparing the transmittance spectra of the resin monomers prepared in example 1 and comparative example 1.
Detailed Description
The invention is further illustrated by the following specific examples, which are not intended to limit the scope of the invention.
Example 1: preparation of quinophthalone compound (formula A), blue light-proof resin monomer and blue light-proof lens
(1) The quinophthalone compound (formula A) is prepared by the following chemical reaction equation:
adding 100g of phthalic anhydride and 380g of 2-methyl-3-hydroxyquinoline into a reaction container, adding 380g of 1, 3, 5-trichlorobenzene as a solvent, slowly heating to 180 ℃, carrying out condensation reaction at the temperature, keeping the temperature for 2 hours, cooling the temperature to room temperature, filtering the mixed product to obtain separated filtrate and filter cake, washing the filter cake with ethanol, drying in a vacuum drying oven at 120 ℃ for 1.5 hours to obtain a light yellow solid, and grinding to obtain a quinophthalone compound, MS: 289.
(2) preparing a blue-light-proof resin monomer: 1.0g of quinophthalone compound (formula A) and 12g of dichloromethane are fully mixed and dissolved, then added into a reaction container containing 1000g of methyl methacrylate monomer (acrylic), 15g of titanium dioxide and 8.0g of ultraviolet absorbent UV-326 are sequentially added, and after uniform mixing, the blue light-proof resin monomer is obtained.
(3) Preparing a blue-light-proof lens: adding 2.5g of initiator dibenzoyl peroxide into the blue-light-proof monomer prepared in the step (2), stirring at a low speed of 200r/min, and controlling the mixture to carry out polymerization reaction at 80 ℃ for 3 hours to complete prepolymerization; filtering the pre-polymerization mixture by a filter screen with the thickness of 1 mu m, degassing, injecting the pre-polymerization mixture into a mold, wherein the thickness of the mold is 3mm, and heating the pre-polymerization mixture to 85 ℃ from room temperature in a curing furnace for 20 hours to finish primary curing; and (3) after the primary curing is finished, opening the die and cleaning, keeping the temperature of the precision curing furnace at 120 ℃ for 2 hours, and finishing secondary curing to obtain the blue-light-proof lens with the specific absorption wavelength.
Example 2: preparation of quinophthalone compound (formula A), blue light-proof resin monomer and blue light-proof lens
(1) Preparation of a quinophthalone compound (formula a): adding 100g of phthalic anhydride and 300g of 2-methyl-3-hydroxyquinoline into a reaction vessel, adding 260g of 1, 3, 5-trichlorobenzene as a solvent, slowly heating to 180 ℃, carrying out condensation reaction at the temperature, keeping the temperature for 2.5 hours, cooling the temperature to room temperature, filtering the mixed product to obtain separated filtrate and filter cake, washing the filter cake with ethanol, drying in a vacuum drying oven at 140 ℃ for 1 hour to obtain a light yellow solid, and grinding to obtain a quinophthalone compound (formula A), MS: 289.
(2) preparing a blue-light-proof resin monomer: 1.0g of quinophthalone compound (formula A) and 15g of dichloromethane are fully mixed and dissolved, then added into a reaction container containing 1400g of methyl methacrylate monomer (acrylic), 10g of titanium dioxide and 20.0g of ultraviolet absorbent UV-531 are sequentially added, and the mixture is uniformly mixed to obtain the blue-light-proof monomer.
(3) Preparing a blue-light-proof lens: 4g of initiator dibenzoyl peroxide (BPO) is added into the blue-light-proof monomer prepared in the step (2), stirred at a low speed of 200r/min, and subjected to polymerization reaction for 3 hours at the temperature of 80 ℃ to complete prepolymerization; filtering the pre-polymerization mixture by a filter screen with the thickness of 1 mu m, degassing, injecting the pre-polymerization mixture into a mold, wherein the thickness of the mold is 3mm, and heating the pre-polymerization mixture to 85 ℃ from room temperature in a curing furnace for 20 hours to finish primary curing; and (3) after the primary curing is finished, opening the die and cleaning, keeping the temperature of the precision curing furnace at 120 ℃ for 2 hours, and finishing secondary curing to obtain the blue-light-proof lens with the specific absorption wavelength.
Example 3: preparation of quinophthalone compound (formula A), blue light-proof resin monomer and blue light-proof lens
(1) Preparation of a quinophthalone compound (formula a): adding 100g of phthalic anhydride and 500g of 2-methyl-3-hydroxyquinoline into a reaction vessel, adding 600g of 1, 3, 5-trichlorobenzene as a solvent, slowly heating to 200 ℃, carrying out condensation reaction at the temperature, keeping the temperature for 3 hours, cooling the temperature to room temperature, filtering the mixed product to obtain separated filtrate and filter cake, washing the filter cake with ethanol, drying in a vacuum drying oven at 100 ℃ for 2 hours to obtain a light yellow solid, and grinding to obtain a quinophthalone compound (formula A), MS: 289.
(2) preparing a blue-light-proof resin monomer: 1.5g of quinophthalone compound (formula A) and 10g of dichloromethane are fully mixed and dissolved, then the mixture is added into a reaction vessel containing 800g of allyl diglycolate monomer (CR39), 20g of titanium dioxide and 4.0g of ultraviolet absorbent UV-329 are sequentially added, and the mixture is uniformly mixed, so that the blue-light-proof monomer is obtained.
(3) Preparing a blue-light-proof lens: 2g of initiator diisopropyl peroxydicarbonate (IPP) is added into the blue-light-proof monomer prepared in the step (2), stirred at a low speed of 200r/min, and subjected to polymerization reaction for 3 hours at the temperature of 45 ℃ to complete prepolymerization; filtering the pre-polymerization mixture by a filter screen with the diameter of 1 mu m, degassing, injecting the mixture into a mold, and heating the mixture to 85 ℃ from room temperature in a curing furnace for 20 hours to finish primary curing; and (3) after the primary curing is finished, opening the die and cleaning, keeping the temperature of the precision curing furnace at 140 ℃ for 2 hours, and finishing the secondary curing to obtain the blue-light-proof resin lens with the specific absorption wavelength.
Example 4: preparation of quinophthalone compound (formula A), blue light-proof resin monomer and blue light-proof lens
(1) Preparation of a quinophthalone compound (formula a): adding 100g of phthalic anhydride and 360g of 2-methyl-3-hydroxyquinoline into a reaction vessel, adding 320g of 1, 3, 5-trichlorobenzene as a solvent, slowly heating to 180 ℃, carrying out condensation reaction at the temperature, keeping the temperature for 2.5 hours, cooling the temperature to room temperature, filtering the mixed product to obtain separated filtrate and filter cake, washing the filter cake with ethanol, drying in a vacuum drying oven at 120 ℃ for 1.5 hours to obtain a light yellow solid, and grinding to obtain a quinophthalone compound (formula A), MS: 289.
(2) preparing a blue-light-proof resin monomer: 1.0g of quinophthalone compound (formula A) and 14g of dichloromethane are fully mixed and dissolved, then added into a reaction vessel containing 900g of 2, 3-dimercaptoethyl thiopropanethiol monomer (BES), 13g of titanium dioxide and 10g of ultraviolet absorbent UV-928 are sequentially added, and after uniform mixing, the blue-light-proof resin monomer is obtained.
(3) Preparing a blue-light-proof lens: mixing and stirring the blue-light-proof resin monomer prepared in the step (2) with 920g of Xylylene Diisocyanate (XDI); adding 20g of dibutyltin Dilaurate (DBTL) catalyst, then carrying out prepolymerization on the mixture at 60 ℃ for 30 minutes, pouring the raw materials into a mold after vacuum defoamation, heating the raw materials to 120 ℃ according to a curing program to enable the raw materials to be cured and molded, then slowly cooling to room temperature, demolding and cleaning to obtain the blue-light-proof resin lens.
Example 5: preparation of quinophthalone compound (formula A), blue light-proof resin monomer and blue light-proof lens
(1) Preparation of a quinophthalone compound (formula a): adding 100g of phthalic anhydride and 450g of 2-methyl-3-hydroxyquinoline into a reaction vessel, adding 500g of 1, 3, 5-trichlorobenzene as a solvent, slowly heating to 160 ℃, carrying out condensation reaction at the temperature, keeping the temperature for 2 hours, cooling the temperature to room temperature, filtering the mixed product to obtain separated filtrate and filter cake, washing the filter cake with ethanol, drying in a 115 ℃ vacuum drying oven for 2 hours to obtain a light yellow solid, and grinding to obtain a quinophthalone compound (formula A), MS: 289.
(2) preparing a blue-light-proof resin monomer: fully mixing and dissolving 1.3g of quinophthalone compound (formula A) and 10g of dichloromethane, adding the mixture into a reaction vessel containing 1200g of 2, 3-dimercaptoethyl thiopropanethiol monomer (BES), sequentially adding 18g of titanium dioxide and 12g of ultraviolet absorbent UV-326, and uniformly mixing to obtain the blue-light-proof resin monomer with a specific absorption wavelength.
(3) Preparing a blue-light-proof lens: mixing and stirring the blue-light-proof single resin body prepared in the step (2) with 1200g of Xylylene Diisocyanate (XDI); adding 28g of dibutyltin dilaurate catalyst (DBTL), then carrying out prepolymerization on the mixture at 60 ℃ for 30 minutes, pouring the raw materials into a mold after vacuum defoamation, heating the raw materials to 120 ℃ according to a curing program to enable the raw materials to be cured and molded, then slowly cooling to room temperature, demolding and cleaning to obtain the blue-light-proof resin lens.
Example 6: detection of heat stability of quinophthalone compound
The heat resistance of the quinophthalone compounds prepared in examples 1 to 5 was examined, respectively, by the following methods: the quinophthalone compound powder prepared in the example and glass microspheres are mixed, placed into a muffle furnace, set at three temperature levels of 200 ℃, 250 ℃ and 300 ℃ for 30 minutes, taken out and dissolved in an ethanol solvent respectively, and the color of the sample is compared with that of a sample which is not heated.
The detection result shows that the hue is not obvious under the conditions of 200 ℃ and 250 ℃ and the hue is obviously changed under the condition of 300 ℃ (the chroma of an unheated sample is transparent yellow, and the hue is semitransparent yellowish under the condition of 300 ℃), so that the heat-resistant temperature of the compound is more than 250 ℃.
Comparative example 1
The quinophthalone compound treated at 300 ℃ in example 6 was selected to prepare blue-light-resistant resin monomers and blue-light-resistant lenses:
(1) preparing a blue-light-proof resin monomer: 1.0g of quinophthalone compound (formula A) and 12g of dichloromethane are fully mixed and dissolved, then added into a reaction container containing 1000g of methyl methacrylate monomer (acrylic), 15g of titanium dioxide and 8.0g of ultraviolet absorbent UV-326 are sequentially added, and after uniform mixing, the blue light-proof monomer is obtained.
(2) Preparing a blue-light-proof lens: adding 2.5g of initiator dibenzoyl peroxide into the blue-light-proof resin monomer prepared in the step (1), stirring at a low speed of 200r/min, and controlling the mixture to carry out polymerization reaction at 80 ℃ for 3 hours to complete prepolymerization; filtering the pre-polymerization mixture by a filter screen with the thickness of 1 mu m, degassing, injecting the pre-polymerization mixture into a mold, wherein the thickness of the mold is 3mm, and heating the pre-polymerization mixture to 85 ℃ from room temperature in a curing furnace for 20 hours to finish primary curing; and (3) opening the mold and cleaning after the primary curing is finished, and keeping the temperature of the precision curing furnace at 120 ℃ for 2 hours to finish secondary curing to obtain the blue-light-proof lens.
Comparative example 2
The quinophthalone compound treated at 250 ℃ in example 6 was selected to prepare blue light-blocking resin monomers and blue light-blocking lenses:
(1) preparing a blue-light-proof resin monomer: 1.0g of quinophthalone compound (formula A) and 12g of dichloromethane are fully mixed and dissolved, then added into a reaction container containing 1000g of methyl methacrylate monomer (acrylic), 15g of titanium dioxide and 8.0g of ultraviolet absorbent UV-326 are sequentially added, and after uniform mixing, the blue light-proof monomer is obtained.
(2) Preparing a blue-light-proof lens: adding 2.5g of initiator dibenzoyl peroxide into the blue-light-proof resin monomer prepared in the step (1), stirring at a low speed of 200r/min, and controlling the mixture to carry out polymerization reaction at 80 ℃ for 3 hours to complete prepolymerization; filtering the pre-polymerization mixture by a filter screen with the thickness of 1 mu m, degassing, injecting the pre-polymerization mixture into a mold, wherein the thickness of the mold is 3mm, and heating the pre-polymerization mixture to 85 ℃ from room temperature in a curing furnace for 20 hours to finish primary curing; and (3) opening the mold and cleaning after the primary curing is finished, and keeping the temperature of the precision curing furnace at 120 ℃ for 2 hours to finish secondary curing to obtain the blue-light-proof lens.
Comparative example 3:
(1) preparing resin monomers:
comparative resin monomer samples 1-5 were prepared using the methods described in examples 1-5, respectively, except that no quinophthalone compound was added.
(2) Preparing a resin lens:
comparative resin lenses 1 to 5 were prepared by the methods for preparing blue light blocking lenses described in examples 1 to 5, respectively, except that the resin monomer prepared in step (1) without adding a quinophthalone compound was used as a monomer.
Example 7: blue light prevention resin monomer and lens optical performance detection
The resin monomers and the lenses prepared in examples 1 to 5 and comparative examples 1 to 3 were respectively tested for light transmittance (T/%) performance, and a UV-8000 type UV-visible spectrophotometer, a Shanghai chromatography apparatus Co., Ltd, was used. Monomer detection method 1: the resin monomers prepared in examples 1 to 5 and comparative examples 1 to 3 were directly coated on a prism of an ultraviolet-visible spectrophotometer to measure light transmittance, and the results of the measurements are shown in tables 1 and 3; the monomer transmittance spectra of the resins prepared in example 1 and comparative example 1 are shown in fig. 1. Lens detection method 2: the resin lenses prepared in examples 1 to 5 and comparative examples 1 to 3 were measured for lens transmittance, and the results of the measurements are shown in tables 2 and 4.
Table 1 unit of blue light-proof resin monomer transmittance test results: t%
Table 2 unit of blue light prevention lens transmittance test results: t%
Table 3 units of results of resin monomer transmittance measurements: t%
Table 4 units of transmittance test results of resin lenses: t%
From the above detection results, it was found that: according to the blue-light-proof resin monomer and the lens with the specific absorption wavelength, the transmittance of an ultraviolet spectrum region (220-; the heat resistant temperature of the quinophthalone compound (formula A) is above 250 ℃.
Claims (3)
1. The application of the quinophthalone compound shown in the formula A as a light absorption material is characterized in that the quinophthalone compound shown in the formula A, nano titanium dioxide with a core-shell structure and an ultraviolet absorbent are dispersed in an optical resin monomer to form a blue light prevention resin monomer; the weight ratio of the quinophthalone compound shown in the formula A, the nano titanium dioxide with the core-shell structure, the ultraviolet absorbent and the optical resin monomer is (0.1-0.2): 0.5-3.0): 0.2-2.0): 100-
（A）
The ultraviolet absorbent is at least one of UV-P, UV-326, UV-327, UV-328, UV-329, UV-360, UV-531 and UV-928;
the optical resin monomer is at least one of methacrylate type monomer, polyurethane type high molecular monomer and allyl type monomer.
2. The use of claim 1, wherein the blue-light preventing resin monomer is polymerized to form a blue-light preventing resin material.
3. The application of claim 1 or 2, wherein the core of the nano titanium dioxide with the core-shell structure is titanium dioxide nano particles with the particle size of 5-20 nm; the shell is a surfactant with the thickness of 2-5nm, and the surfactant is polyvinylpyrrolidone or sodium dodecyl benzene sulfonate.
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| CN115850995B (en) * | 2022-12-09 | 2023-12-12 | 河北中化鑫宝化工科技有限公司 | Preparation method of solvent yellow 33 |
| CN116731498A (en) * | 2023-06-09 | 2023-09-12 | 江苏视科新材料股份有限公司 | Blue light-proof photochromic resin lens |
| CN116854958A (en) * | 2023-06-09 | 2023-10-10 | 江苏视科新材料股份有限公司 | Preparation method of blue light prevention photochromic lens substrate |
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