CN111620885A - Poly R-indole blue light absorber and preparation method and application thereof - Google Patents
Poly R-indole blue light absorber and preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to a poly R-indole blue light absorbent, a preparation method and application thereof. The poly R-indole blue light absorber is a mixture of series of oligomers obtained from R-indole by a free radical oxidation process. The poly R-indole blue light absorbent has stronger absorption capacity to ultraviolet and short-wave blue light wave bands of 400-480nm, and has extremely high transmission capacity to visible light above 500 nm. In addition, the resin has better solubility in nonpolar solvents and resin monomers, and is suitable for resin spectacle lenses, high polymer material films and coatings.
Description
Technical Field
The invention belongs to the technical field of new materials, and particularly relates to a poly R-indole blue light absorbent, and a preparation method and application thereof.
Background
With the development of communication technology, the usage rate of electronic products such as mobile phones, computers, televisions and the like is higher and higher. However, the high-energy blue light projected by the screens of these electronic products is harmful to human health. According to the present research, the blue light emitted by these electronic products is high in energy and can penetrate through the crystalline lens to reach the retina, so that the photosensitive cells are damaged, and the vision is damaged. Secondly, the blue light can inhibit the secretion of melatonin, so as to cause symptoms of insomnia, anxiety and the like. Moreover, high-energy blue light easily causes blurred vision and visual fatigue of people, and may even induce diseases such as macular degeneration, cataract and the like. The blue light can excite brown pigment, and make skin generate macula lutea and freckle.
In order to reduce the harm of blue light, particularly short-wave blue light with the wavelength of 400-.
Currently, some of the prior research results on blue-light absorbers are presented below:
patent 201510611587.4 discloses a carotenoid acrylate blue-light absorber and a preparation method thereof, wherein carotenoid is prepared into carotenoid acrylate, and then the carotenoid acrylate is polymerized to obtain a carotenoid acrylate solid. The blue light absorbent has the blue light transmittance controlled below 40% for the wavelength below 450nm and the blue light absorption controlled below 30% for the wavelength above 460nm, and can regulate the blue light without causing color distortion of the display screen. However, from the data provided in the patent, the blue light absorber has about 10% absorption of visible light at 500-700nm, and the light transmittance is insufficient.
Patent 201711347842.4 discloses a 3, 3' - (1, 3-phenylene) bis [1- (alkoxyphenyl) -1,3- ] propanedione ] ultraviolet-blue light absorber and is used for preparing an ultraviolet-blue light absorbing material which can absorb high-energy ultraviolet light and part of short-wave blue light. But the absorption peak is at 340-440nm, and has no absorption effect on blue light at 440-480.
Patent 201710561713.9 discloses a blue light absorbent containing three benzene rings and pyrazole structure, which has better absorption to light with wavelength of 300-450nm, good heat resistance, and better compatibility with ethylene terephthalate, and is suitable for polyester films. However, the synthesis of the blue light absorbent is complex and the cost is high.
Patent 201780010286.3 discloses a blue-light cut-off optical material containing benzotriazole UV absorber, which has a transmittance of less than 1% for light with wavelength of 280-400nm and a transmittance of more than 65% for light with wavelength of 430nm, and can be used in resin lenses. According to data given by the patent, the light cut-off wavelength is 400-410 nm, the transmittance of the light with the wavelength of 440nm which has the greatest harm is over 80%, and the blue light blocking effect is not ideal.
Patent 201910525567.3 discloses a UV-blue light absorber containing quinolyl and conjugated olefin structure, which has a relatively obvious blue light absorption effect and can be used in the technical fields of plastics, coatings, inks, lighting, glasses and the like. However, the raw materials are expensive, the absorbent structure is complex, and the synthesis is difficult.
It can be seen that the problems with the prior art blue-light absorbers include: poor blue light blocking effect, insufficient light transmittance, complex synthesis process and the like.
Disclosure of Invention
The invention aims to provide a poly R-indole blue light absorbent, a preparation method and application thereof. The blue light absorbent can efficiently absorb ultraviolet light and short-wave blue light of 400-480nm, and has near zero absorption on visible light above 500nm, and in addition, the raw material source is wide, the synthesis method is simple and convenient, and the cost is low.
The purpose of the invention can be realized by the following technical scheme:
the invention provides a poly R-indole blue light absorber, which has a structure represented by the following general formula:
wherein n-1-6, R represents a substituent attached to a benzene ring, and one or two substituents attached to one benzene ring, R is selected from-CH3、-C2H5、-C(CH3)3、-CN、-F、-Cl、-Br、-I、-COOH、-OH、-CH2OH、-C2H5OH、-CH2COOH、-NH2、-CHO、-NO2、-COOCH3、-COOC2H5、-B(OH)2、-COCH3、-CH2COOCH3、-CH2COOC2H5、-OOCCH3、-OOCC2H5、-OCH3、-OC2H5、-CF3、-0C6H5or-OCH2C6H5One or more of them.
The invention also provides a preparation method of the poly R-indole blue light absorbent, wherein the poly R-indole blue light absorbent is obtained by indole monomers through a free radical oxidation method;
the indole monomer has a structure represented by the following general formula, and is also called R-indole:
wherein R represents a substituent group attached to a benzene ring, and one or two substituent groups attached to one benzene ring, R is selected from-CH3、-C2H5、-C(CH3)3、-CN、-F、-Cl、-Br、-I、-COOH、-OH、-CH2OH、-C2H5OH、-CH2COOH、-NH2、-CHO、-NO2、-COOCH3、-COOC2H5、-B(OH)2、-COCH3、-CH2COOCH3、-CH2COOC2H5、-OOCCH3、-OOCC2H5、-OCH3、-OC2H5、-CF3、-0C6H5or-OCH2C6H5；
The free radical oxidation method is selected from an oxidant oxidation method or an ultraviolet oxidation method;
the steps of the oxidant oxidation process include: mixing indole monomer, oxidant and solvent according to the mass ratio of 1 (0.5-5) to (0-500), reacting at 0-150 ℃ for 1-168h, and removing the solvent to obtain the poly R-indole blue light absorber.
The oxidant is selected from one or more of ferric trichloride, potassium dichromate, ammonium persulfate, sodium persulfate, potassium persulfate, sodium percarbonate, ozone, benzoyl peroxide, dicumyl peroxide or isobenzoyl hydrogen peroxide;
the solvent is one or more selected from water, methanol, ethanol, acetone, dimethylformamide, dimethyl sulfoxide, ethyl acetate, chloroform, dichloromethane, benzene, toluene, xylene, tetrahydrofuran or methyl pyrrolidone.
The ultraviolet oxidation method comprises the following steps: the indole monomer, the photoinitiator and the solvent are uniformly mixed according to the mass ratio of 1 (0.5-5) to 0-500, the mixture is irradiated for 0.1-24 hours under ultraviolet light, and the solvent is removed to obtain the poly R-indole blue light absorber.
The photoinitiator is selected from one or more of benzophenone, 2, 4-dihydroxy benzophenone, 4' -bis (dimethylamino) benzophenone, diphenylethanone, 2-hydroxy-2-methyl-1-phenyl acetone or 1-hydroxycyclohexyl phenyl ketone;
the wavelength of the ultraviolet light is 250-400 nm;
the solvent is one or more selected from water, methanol, ethanol, acetone, dimethylformamide, dimethyl sulfoxide, ethyl acetate, chloroform, dichloromethane, benzene, toluene, xylene, tetrahydrofuran or methyl pyrrolidone.
The poly R-indole blue light absorber is a mixture of series oligomers obtained by a free radical oxidation method from R-indole.
The poly R-indole blue light absorbent has stronger absorption capacity to ultraviolet and short-wave blue light wave bands of 400-480nm, and has extremely high transmission capacity to visible light above 500 nm; the poly R-indole blue light absorber has better solubility in a non-polar solvent and a resin monomer.
The invention also provides application of the poly R-indole blue light absorbent, and the poly R-indole blue light absorbent is used for preparing resin lenses, high polymer material films and high polymer material coatings.
The technical solution of the present invention is further explained and illustrated below:
the R-indole is an indole derivative, the indole ring has pi electron conjugation characteristic, and has obvious absorption characteristic on ultraviolet, as shown in figure 1, but almost has no absorption effect on blue light. In the oxidation process, the oxidant abstracts hydrogen at 2-position and 3-position of R-indole to cause coupling between the R-indole, and the coupled poly R-indole has a larger pi electron conjugated structure to enable the position of an absorption peak to be red-shifted. The blue light absorption band can be controlled by controlling the degree of oxidation. The substituent R may participate in partial conjugation, and thus changing the kind of R may also affect the absorption peak to light. The solubility of the poly R-indole blue light absorber in different solvents can be adjusted by adjusting the type of the substituent R, thereby expanding the application performance.
Compared with the prior art, the invention has the advantages that:
the poly R-indole blue light absorbent has stronger absorption capacity to ultraviolet and short-wave blue light wave bands of 400-480nm, and has extremely high transmission capacity to visible light above 500 nm; has better solubility in non-polar solvent and resin monomer, and is suitable for resin spectacle lenses, high polymer material films and coatings. In addition, the poly R-indole blue light absorbent provided by the invention has the advantages of wide raw material source, simple and convenient synthesis method and low cost.
Drawings
FIG. 1 is a UV-vis absorption spectrum of indole 7-carboxylate and indole poly-7-carboxylate in example 1.
The dotted line represents indole-7-carboxylate and the solid line represents indole-7-methyl-carboxylate.
FIG. 2 shows the absorption effect of a CR39 lens (1mm thick) with addition of poly 5-cyanoindole (200ppm) on the screen light source of a mobile phone. The dotted line represents the light source of the mobile phone screen, and the solid line represents the light source filtered by the polybenzazole lens.
Detailed Description
Provided is a poly R-indole blue light absorber having a structure represented by the following general formula:
wherein n-1-6, R represents a substituent attached to a benzene ring, and one or two substituents attached to one benzene ring, R is selected from-CH3、-C2H5、-C(CH3)3、-CN、-F、-Cl、-Br、-I、-COOH、-OH、-CH2OH、-C2H5OH、-CH2COOH、-NH2、-CHO、-NO2、-COOCH3、-COOC2H5、-B(OH)2、-COCH3、-CH2COOCH3、-CH2COOC2H5、-OOCCH3、-OOCC2H5、-OCH3、-OC2H5、-CF3、-0C6H5or-OCH2C6H5One or more of them.
Also provides a preparation method of the poly R-indole blue light absorbent, and the poly R-indole blue light absorbent is obtained by indole monomers through a free radical oxidation method;
the indole monomer has a structure represented by the following general formula, and is also called R-indole:
wherein R represents a substituent group attached to a benzene ring, and one or two substituent groups attached to one benzene ring, R is selected from-CH3、-C2H5、-C(CH3)3、-CN、-F、-Cl、-Br、-I、-COOH、-OH、-CH2OH、-C2H5OH、-CH2COOH、-NH2、-CHO、-NO2、-COOCH3、-COOC2H5、-B(OH)2、-COCH3、-CH2COOCH3、-CH2COOC2H5、-OOCCH3、-OOCC2H5、-OCH3、-OC2H5、-CF3、-0C6H5or-OCH2C6H5；
The free radical oxidation method is selected from an oxidant oxidation method or an ultraviolet oxidation method;
the steps of the oxidant oxidation process include: mixing indole monomer, oxidant and solvent according to the mass ratio of 1 (0.5-5) to (0-500), reacting at 0-150 ℃ for 1-168h, and removing the solvent to obtain the poly R-indole blue light absorber.
The oxidant is selected from one or more of ferric trichloride, potassium dichromate, ammonium persulfate, sodium persulfate, potassium persulfate, sodium percarbonate, ozone, benzoyl peroxide, dicumyl peroxide or isobenzoyl hydrogen peroxide;
the solvent is one or more selected from water, methanol, ethanol, acetone, dimethylformamide, dimethyl sulfoxide, ethyl acetate, chloroform, dichloromethane, benzene, toluene, xylene, tetrahydrofuran or methyl pyrrolidone.
The ultraviolet oxidation method comprises the following steps: the indole monomer, the photoinitiator and the solvent are uniformly mixed according to the mass ratio of 1 (0.5-5) to 0-500, the mixture is irradiated for 0.1-24 hours under ultraviolet light, and the solvent is removed to obtain the poly R-indole blue light absorber.
The photoinitiator is selected from one or more of benzophenone, 2, 4-dihydroxy benzophenone, 4' -bis (dimethylamino) benzophenone, diphenylethanone, 2-hydroxy-2-methyl-1-phenyl acetone or 1-hydroxycyclohexyl phenyl ketone;
the wavelength of the ultraviolet light is 250-400 nm;
the solvent is one or more selected from water, methanol, ethanol, acetone, dimethylformamide, dimethyl sulfoxide, ethyl acetate, chloroform, dichloromethane, benzene, toluene, xylene, tetrahydrofuran or methyl pyrrolidone.
The invention also provides application of the poly R-indole blue light absorbent, and the poly R-indole blue light absorbent is used for preparing resin lenses, high polymer material films and high polymer material coatings.
The invention is described in detail below with reference to the figures and specific embodiments.
Example 1
1 part of 7-methyl indole formate, 3 parts of anhydrous ferric chloride and 100 parts of chloroform are uniformly mixed in a reactor, stirred and reacted for 48 hours at room temperature, impurities are filtered out, the solvent is evaporated to obtain a crude product of poly-7-methyl indole formate, and then the crude product of poly-7-methyl indole formate is purified by an acetone/water dissolution precipitation method to obtain the poly-7-methyl indole formate.
7-methyl indole formate and 7-methyl indole formate were prepared into 50ppm ethanol solution, and ultraviolet-visible spectrum analysis was performed, the results are shown in FIG. 1.
The poly-7-methyl indole formate is added into a spectacle lens resin monomer, the addition amount is 0.1 wt%, then the monomer is solidified into a sheet with the thickness of 1mm, the absorption effect of the sheet on mobile phone screen light is tested, and the absorption ratio of blue light, yellow light and red light is recorded.
Example 2
1 part of 5-cyanoindole and 2 parts of sodium persulfate are uniformly mixed in a mortar, placed at 50 ℃ for 24 hours and then purified by an acetone/water dissolution precipitation method to obtain the poly-5-cyanoindole.
Poly-5-methyl indole formate was added to a spectacle lens resin monomer in an amount of 0.1 wt%, and then cured into a sheet of 1mm thickness, and its absorption effect on mobile phone screen light (FIG. 2) was tested to record the absorption ratio of blue light, yellow light and red light.
Example 3
1 part of 4, 6-difluoroindole, 2 parts of benzoyl peroxide and 50 parts of benzene are uniformly mixed in a reactor, stirred and reacted for 20 hours at the temperature of 80 ℃, the solvent is removed under reduced pressure to obtain a crude product of poly-4, 6-difluoroindole, and then the crude product of poly-4, 6-difluoroindole is purified by an acetone/water dissolution precipitation method to obtain the poly-4, 6-difluoroindole.
Poly 4, 6-difluoroindole was added to a spectacle lens resin monomer in an amount of 0.1 wt%, and then cured into a sheet 1mm thick, and its absorption effect on mobile phone screen light was tested, and the absorption ratios of blue light, yellow light and red light were recorded.
Example 4
1 part of 5-aminoindole, 2 parts of ammonium persulfate and 50 parts of deionized water are uniformly mixed in a reactor, stirred and reacted for 72 hours at the temperature of 30 ℃, filtered to obtain a crude product poly-5-aminoindole, and then purified by an acetone/water dissolution precipitation method to obtain the poly-5-aminoindole.
Adding poly-5-aminoindole into a spectacle lens resin monomer, wherein the addition amount is 0.1 wt%, curing into a sheet with the thickness of 1mm, testing the absorption effect of the sheet on mobile phone screen light, and recording the absorption ratio of blue light, yellow light and red light.
Example 5
1 part of 5-nitroindole, 1 part of benzophenone and 10 parts of dimethylformamide are uniformly mixed in a beaker, the mixture is irradiated for 30min under an ultraviolet lamp of 365nm, a crude product of poly-5-nitroindole is obtained by evaporating the solvent, and then the crude product of poly-5-nitroindole is purified by an acetone/water dissolution precipitation method to obtain the poly-5-nitroindole.
Adding poly-5-nitroindole into a spectacle lens resin monomer, wherein the addition amount is 0.1 wt%, then curing into a sheet with the thickness of 1mm, testing the absorption effect of the sheet on mobile phone screen light, and recording the absorption ratio of blue light, yellow light and red light.
Example 6
1 part of 5, 6-dimethoxy indole and 1 part of 2, 4-dihydroxy benzophenone are uniformly mixed in a beaker, irradiated for 60min under an ultraviolet lamp of 365nm, and then purified by an acetone/water dissolution precipitation method to obtain the poly-5, 6-dimethoxy indole.
Adding poly-5, 6-dimethoxy indole into spectacle lens resin monomer, adding 0.1 wt%, curing into 1mm thick sheet, testing its absorption effect on mobile phone screen light, and recording the absorption ratio of blue light, yellow light and red light.
The results of the tests of examples 1-6 are as follows:
the results show that the poly R-indoles are very suitable as blue light absorbers for blue-blocking ophthalmic lenses. A small amount of poly R-indole is added, so that part of blue light can be obviously absorbed, and yellow light and red light are absorbed less.
The polybenzazole prepared in examples 1 to 6 was dissolved in cyclohexane, toluene, methyl methacrylate, ethanol and water, respectively. The dissolution performance was qualitatively judged by comparing the dissolution rate at 0.1% addition with the transparency of the observed solution. The results were summarized as excellent solubility (++), good solubility (++), with simple shaking for 1 minute, good solubility (++), with most of the solution dissolved in 1 minute, and orange translucency for 1 minute, and insoluble (-) with most of the solution undissolved in 1 minute, as follows:
| solvent(s) | Cyclohexane | Toluene | Methacrylic acid methyl ester | Ethanol | Water (W) |
| Example 1 | + | ++ | +++ | ++ | - |
| Example 2 | + | ++ | +++ | +++ | + |
| Example 3 | - | ++ | ++ | +++ | - |
| Example 4 | - | ++ | ++ | +++ | ++ |
| Example 5 | - | ++ | +++ | +++ | + |
| Example 6 | ++ | +++ | +++ | ++ | - |
In the table, toluene and ethanol are industrially used as a solvent, cyclohexane represents a nonpolar solvent, water belongs to a polar solvent, and methyl methacrylate is a polymerizable ester monomer. The result shows that the solubility of the polybenzazole has a certain relationship with the types of the substituents thereof, and the polybenzazole with proper substituents can be selected according to the principle of similarity and compatibility when different systems are applied.
The embodiments described above are described to facilitate an understanding and use of the invention by those skilled in the art. It will be readily apparent to those skilled in the art that various modifications to these embodiments may be made, and the generic principles described herein may be applied to other embodiments without the use of the inventive faculty. Therefore, the present invention is not limited to the above embodiments, and those skilled in the art should make improvements and modifications within the scope of the present invention based on the disclosure of the present invention.
Claims (10)
1. A poly R-indole blue light absorber having a structure represented by the general formula:
wherein n-1-6, R represents a substituent attached to a benzene ring, and one or two substituents attached to one benzene ring, R is selected from-CH3、-C2H5、-C(CH3)3、-CN、-F、-Cl、-Br、-I、-COOH、-OH、-CH2OH、-C2H5OH、-CH2COOH、-NH2、-CHO、-NO2、-COOCH3、-COOC2H5、-B(OH)2、-COCH3、-CH2COOCH3、-CH2COOC2H5、-OOCCH3、-OOCC2H5、-OCH3、-OC2H5、-CF3、-0C6H5or-OCH2C6H5One or more of them.
2. The process for preparing R-indole blue-light absorber according to claim 1, wherein the poly R-indole blue-light absorber is obtained from indole monomers by a free radical oxidation method;
the indole monomer has a structure represented by the following general formula:
wherein R represents a substituent group attached to a benzene ring, and one or two substituent groups attached to one benzene ring, R is selected from-CH3、-C2H5、-C(CH3)3、-CN、-F、-Cl、-Br、-I、-COOH、-OH、-CH2OH、-C2H5OH、-CH2COOH、-NH2、-CHO、-NO2、-COOCH3、-COOC2H5、-B(OH)2、-COCH3、-CH2COOCH3、-CH2COOC2H5、-OOCCH3、-OOCC2H5、-OCH3、-OC2H5、-CF3、-0C6H5or-OCH2C6H5。
3. The method of preparing R-indole blue light absorber according to claim 2, wherein the free radical oxidation process is selected from the group consisting of oxidant oxidation;
the steps of the oxidant oxidation process include: mixing indole monomer, oxidant and solvent according to the mass ratio of 1 (0.5-5) to (0-500), reacting at 0-150 ℃ for 1-168h, and removing the solvent to obtain the poly R-indole blue light absorber.
4. The method for preparing R-indole blue light absorber according to claim 3, wherein the oxidant is selected from one or more of ferric trichloride, potassium dichromate, ammonium persulfate, sodium persulfate, potassium persulfate, sodium percarbonate, ozone, benzoyl peroxide, dicumyl peroxide or isoacene hydrogen peroxide.
5. The method for preparing R-indole blue-ray absorber according to claim 3, wherein the solvent is one or more selected from water, methanol, ethanol, acetone, dimethylformamide, dimethyl sulfoxide, ethyl acetate, chloroform, dichloromethane, benzene, toluene, xylene, tetrahydrofuran and methylpyrrolidone.
6. The method of preparing R-indole blue light absorber according to claim 2, wherein the free radical oxidation process is selected from the group consisting of uv oxidation;
the ultraviolet oxidation method comprises the following steps: the indole monomer, the photoinitiator and the solvent are uniformly mixed according to the mass ratio of 1 (0.5-5) to 0-500, the mixture is irradiated for 0.1-24 hours under ultraviolet light, and the solvent is removed to obtain the poly R-indole blue light absorber.
7. The method for preparing R-indole blue light absorber according to claim 6, wherein the photoinitiator is selected from one or more of benzophenone, 2, 4-dihydroxybenzophenone, 4' -bis (dimethylamino) benzophenone, diphenylethanone, 2-hydroxy-2-methyl-1-phenylpropanone, or 1-hydroxycyclohexyl phenyl methanone.
8. The method for preparing R-indole blue-light absorber according to claim 6, wherein the wavelength of the ultraviolet light is 250-400 nm.
9. The method for preparing R-indole blue-ray absorber according to claim 6, wherein the solvent is one or more selected from water, methanol, ethanol, acetone, dimethylformamide, dimethyl sulfoxide, ethyl acetate, chloroform, dichloromethane, benzene, toluene, xylene, tetrahydrofuran and methylpyrrolidone.
10. The use of the R-indole blue-light absorber according to claim 1, wherein the poly R-indole blue-light absorber is used for the preparation of resin lenses, polymer material films, polymer material coatings.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114031547A (en) * | 2021-11-01 | 2022-02-11 | 上海甘田光学材料有限公司 | Indole compound and application thereof |
| CN115521523A (en) * | 2022-09-15 | 2022-12-27 | 青岛上雅家居用品股份有限公司 | Hose with blue light prevention function and preparation method thereof |
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| CN115521523A (en) * | 2022-09-15 | 2022-12-27 | 青岛上雅家居用品股份有限公司 | Hose with blue light prevention function and preparation method thereof |
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| CN111620885B (en) | 2023-05-30 |
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