CN111620885B - 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
- Publication number
- CN111620885B CN111620885B CN202010616671.6A CN202010616671A CN111620885B CN 111620885 B CN111620885 B CN 111620885B CN 202010616671 A CN202010616671 A CN 202010616671A CN 111620885 B CN111620885 B CN 111620885B
- Authority
- CN
- China
- Prior art keywords
- indole
- poly
- blue light
- light absorber
- oxidation method
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
- C08K5/3417—Five-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/48—Stabilisers against degradation by oxygen, light or heat
Abstract
The invention relates to a poly R-indole blue light absorber and 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 method. The poly R-indole blue light absorber has strong absorption capacity to ultraviolet and short wave blue light wave bands of 400-480nm, and has extremely high transmission capacity to visible light of more than 500 nm. In addition, the polymer has better solubility in nonpolar solvents and resin monomers, and is suitable for being applied to resin spectacle lenses, 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 absorber, and a preparation method and application thereof.
Background
With the development of communication technology, the use rate of electronic products such as mobile phones, computers, televisions and the like is increasing. However, the high-energy blue light projected by these electronic product screens is harmful to human health. According to the present research, the blue light emitted by the electronic products has high energy and can penetrate through the crystalline lens to reach the retina, damage photosensitive cells and cause vision injury. Secondly, blue light can inhibit melatonin secretion, and causes symptoms such as insomnia, dysphoria and the like. Furthermore, high-energy blue light is easy to cause people to have blurred vision and visual fatigue, and even can induce diseases such as maculopathy, cataract and the like. Blue light can excite brown pigment to make skin produce macula and freckle.
In order to reduce the damage of blue light, especially short-wave blue light with the wavelength of 400-480nm, the blue light absorbent is applied to materials such as spectacle lenses, screen films, lamp covers and the like, and effectively plays a role in protection.
Currently, some of the current research efforts 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 polymerized to obtain a carotenoid acrylate solid. The blue light absorber has a blue light transmittance of below 40% for a wavelength below 450nm and a blue light absorptivity of below 30% for a wavelength above 460nm, and can realize blue light adjustment without causing color distortion of a display screen. However, from the data provided in this patent, the blue light absorber has about 10% absorption of 500-700nm visible light, 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, which is used for preparing an ultraviolet-blue light absorbing material and can absorb high-energy ultraviolet light and partial short-wave blue light. But has absorption peak at 340-440nm, and has no absorption effect on blue light at 440-480.
Patent 201710561713.9 discloses a blue light absorber containing three benzene rings and a pyrazole structure, which has good absorption to light with the wavelength of 300-450nm, good heat resistance and good compatibility with ethylene terephthalate, and is suitable for a blue light absorber of a polyester film. However, the blue light absorber is complex to synthesize and has high cost.
Patent 201780010286.3 discloses a blue light cut-off optical material comprising a benzotriazole uv absorber having a transmittance of less than 1% for light of 280-400nm wavelength and a transmittance of more than 65% for light of 430nm wavelength, which can be used in a resin lens. From the data given in the patent, the light cut-off wavelength is 400-410 nm, and the transmittance for the wavelength of 440nm which is the biggest hazard is more than 80%, and the blue light blocking effect is not ideal.
Patent 201910525567.3 discloses an ultraviolet-blue light absorbent containing quinolinyl and conjugated alkene structure, which has obvious blue light absorption effect and can be used in the technical fields of plastics, paint, printing ink, illumination, glasses and the like. However, the raw materials are expensive, the absorbent structure is complex, and the synthesis is difficult.
As can be seen, problems with the blue light absorber of the prior art 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 absorber, and a preparation method and application thereof. The blue light absorber can efficiently absorb ultraviolet light and short-wave blue light of 400-480nm, can absorb visible light of more than 500nm near zero, and has the advantages of wide raw material sources, simple synthesis method and low cost.
The aim of the invention can be achieved 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 to 6, R represents a substituent attached to a benzene ring, and one or two substituents attached to one benzene ring, R is selected from-CH 3 、-C 2 H 5 、-C(CH 3 ) 3 、-CN、-F、-Cl、-Br、-I、-COOH、-OH、-CH 2 OH、-C 2 H 5 OH、-CH 2 COOH、-NH 2 、-CHO、-NO 2 、-COOCH 3 、-COOC 2 H 5 、-B(OH) 2 、-COCH 3 、-CH 2 COOCH 3 、-CH 2 COOC 2 H 5 、-OOCCH 3 、-OOCC 2 H 5 、-OCH 3 、-OC 2 H 5 、-CF 3 、-0C 6 H 5 or-OCH 2 C 6 H 5 One or more of them.
The invention also provides a preparation method of the poly R-indole blue light absorber, which is obtained by using 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 attached to the benzene ring, and one or two substituents attached to one benzene ring, R is selected from-CH 3 、-C 2 H 5 、-C(CH 3 ) 3 、-CN、-F、-Cl、-Br、-I、-COOH、-OH、-CH 2 OH、-C 2 H 5 OH、-CH 2 COOH、-NH 2 、-CHO、-NO 2 、-COOCH 3 、-COOC 2 H 5 、-B(OH) 2 、-COCH 3 、-CH 2 COOCH 3 、-CH 2 COOC 2 H 5 、-OOCCH 3 、-OOCC 2 H 5 、-OCH 3 、-OC 2 H 5 、-CF 3 、-0C 6 H 5 or-OCH 2 C 6 H 5 ；
The free radical oxidation method is selected from an oxidant oxidation method or an ultraviolet oxidation method;
the steps of the oxidant oxidation method comprise: the indole monomer, the oxidant and the solvent are mixed according to the mass ratio of 1 (0.5-5) to 0-500, and react for 1-168 hours at the temperature of 0-150 ℃ to obtain the poly R-indole blue light absorber after removing the solvent.
The oxidant is one or more selected from ferric trichloride, potassium dichromate, ammonium persulfate, sodium persulfate, potassium persulfate, sodium percarbonate, ozone, benzoyl peroxide, dicumyl peroxide and isobenzol 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, and are irradiated for 0.1-24 hours under ultraviolet light, and the solvent is removed, so that the poly R-indole blue light absorber is obtained.
The photoinitiator is selected from one or more of benzophenone, 2, 4-dihydroxybenzophenone, 4' -bis (dimethylamino) benzophenone, diphenylethanone, 2-hydroxy-2-methyl-1-phenylpropion or 1-hydroxycyclohexyl phenyl ketone;
the wavelength of the ultraviolet light is 250-400nm;
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 of oligomers obtained from R-indole through a free radical oxidation method.
The poly R-indole blue light absorber has strong 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 nonpolar solvents and resin monomers.
The invention also provides application of the poly R-indole blue light absorber, which is used for preparing resin lenses, polymer material films and polymer material coatings.
The technical scheme of the invention is further explained and illustrated as follows:
r-indole is indole derivative, indole ring has pi electron conjugated characteristic, has obvious absorption characteristic to ultraviolet, and has almost no absorption effect to blue light, as shown in figure 1. In the oxidation process, the oxidant abstracts the hydrogen at the 2 and 3 positions of the R-indole to cause the coupling between the R-indole, and the coupled poly R-indole has a larger pi electron conjugated structure to enable the absorption peak position to be red shifted. The blue absorption band can be controlled by controlling the degree of oxidation. The substituent R may participate in partial conjugation, so changing the kind of R also affects the absorption peak for light. The solubility of the poly R-indole blue light absorber in different solvents can be regulated by regulating the type of the substituent R, so that the application performance is expanded.
Compared with the prior art, the invention has the advantages that:
the poly R-indole blue light absorber has strong 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 polymer has better solubility in nonpolar solvents and resin monomers, and is suitable for being applied to resin spectacle lenses, polymer material films and coatings. In addition, the poly R-indole blue light absorber provided by the invention has the advantages of wide raw material sources, simple and convenient synthesis method and low cost.
Drawings
FIG. 1 is an ultraviolet-visible light absorption spectrum of 7-methyl indole formate and poly 7-methyl indole formate in example 1.
The dashed line represents 7-methyl indole formate and the solid line represents poly 7-methyl indole formate.
FIG. 2 is the effect of absorbing light from a cell phone screen with a CR39 lens (1 mm thick) with poly 5-nitriloindole (200 ppm) added. The dotted line represents the cell phone screen light source and the solid line represents the light source after the polybenzazole lens is filtered.
Detailed Description
Provided is a poly R-indole blue light absorber having a structure represented by the following general formula:
wherein n=1 to 6, R represents a substituent attached to a benzene ring, and one or two substituents attached to one benzene ring, R is selected from-CH 3 、-C 2 H 5 、-C(CH 3 ) 3 、-CN、-F、-Cl、-Br、-I、-COOH、-OH、-CH 2 OH、-C 2 H 5 OH、-CH 2 COOH、-NH 2 、-CHO、-NO 2 、-COOCH 3 、-COOC 2 H 5 、-B(OH) 2 、-COCH 3 、-CH 2 COOCH 3 、-CH 2 COOC 2 H 5 、-OOCCH 3 、-OOCC 2 H 5 、-OCH 3 、-OC 2 H 5 、-CF 3 、-0C 6 H 5 or-OCH 2 C 6 H 5 One or more of them.
The preparation method of the poly R-indole blue light absorber is also provided, and the poly R-indole blue light absorber is obtained by an indole monomer 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 attached to the benzene ring, and one or two substituents attached to one benzene ring, R is selected from-CH 3 、-C 2 H 5 、-C(CH 3 ) 3 、-CN、-F、-Cl、-Br、-I、-COOH、-OH、-CH 2 OH、-C 2 H 5 OH、-CH 2 COOH、-NH 2 、-CHO、-NO 2 、-COOCH 3 、-COOC 2 H 5 、-B(OH) 2 、-COCH 3 、-CH 2 COOCH 3 、-CH 2 COOC 2 H 5 、-OOCCH 3 、-OOCC 2 H 5 、-OCH 3 、-OC 2 H 5 、-CF 3 、-0C 6 H 5 or-OCH 2 C 6 H 5 ；
The free radical oxidation method is selected from an oxidant oxidation method or an ultraviolet oxidation method;
the steps of the oxidant oxidation method comprise: the indole monomer, the oxidant and the solvent are mixed according to the mass ratio of 1 (0.5-5) to 0-500, and react for 1-168 hours at the temperature of 0-150 ℃ to obtain the poly R-indole blue light absorber after removing the solvent.
The oxidant is one or more selected from ferric trichloride, potassium dichromate, ammonium persulfate, sodium persulfate, potassium persulfate, sodium percarbonate, ozone, benzoyl peroxide, dicumyl peroxide and isobenzol 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, and are irradiated for 0.1-24 hours under ultraviolet light, and the solvent is removed, so that the poly R-indole blue light absorber is obtained.
The photoinitiator is selected from one or more of benzophenone, 2, 4-dihydroxybenzophenone, 4' -bis (dimethylamino) benzophenone, diphenylethanone, 2-hydroxy-2-methyl-1-phenylpropion or 1-hydroxycyclohexyl phenyl ketone;
the wavelength of the ultraviolet light is 250-400nm;
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 absorber, which is used for preparing resin lenses, polymer material films and polymer material coatings.
The invention will now be described in detail with reference to the drawings and specific examples.
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 at room temperature for 48 hours for reaction, filtered to remove impurities, the solvent is evaporated to obtain a crude product of the 7-methyl indole formate, and then the crude product of the 7-methyl indole formate is purified by an acetone/water dissolution precipitation method to obtain the 7-methyl indole formate.
The 7-methyl indole formate and the poly 7-methyl indole formate are respectively prepared into 50ppm concentration ethanol solutions, and ultraviolet-visible light spectrum analysis is carried out, and the result is shown in figure 1.
Poly (7-methyl indole formate) is added into an ophthalmic lens resin monomer in an amount of 0.1wt%, and then cured into a sheet with a thickness of 1mm, and the absorption effect of the sheet on the screen light of the mobile phone is tested, and the absorption ratio of blue light, yellow light and red light is recorded.
Example 2
1 part of 5-nitrile indole 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 poly-5-nitrile indole.
Poly (methyl 5-carboxylate) indole was added to the ophthalmic lens resin monomer in an amount of 0.1wt% and then cured into a 1mm thick sheet, which was tested for its light absorption effect on the mobile phone screen (FIG. 2), recording the absorption ratio of blue, yellow 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 at 80 ℃ for reaction for 20 hours, the solvent is removed under reduced pressure to obtain a crude product of poly 4, 6-difluoroindole, and then the poly 4, 6-difluoroindole is obtained by purifying by an acetone/water dissolution precipitation method.
Poly 4, 6-difluoroindole is added into an ophthalmic lens resin monomer in an amount of 0.1wt%, and then cured into a sheet with a thickness of 1mm, and the absorption effect of the sheet on the screen light of the mobile phone is tested, and the absorption ratio of blue light, yellow light and red light is 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 30 ℃, filtered to obtain a crude product of poly-5-aminoindole, and then purified by an acetone/water dissolution precipitation method to obtain the poly-5-aminoindole.
Poly-5-aminoindole was added to the ophthalmic lens resin monomer in an amount of 0.1wt% and then cured into a 1mm thick sheet, which was tested for its light absorption effect on the mobile phone screen and recorded the absorption ratio of blue, yellow 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, irradiated for 30min under an ultraviolet lamp of 365nm, the solvent is evaporated to obtain a crude product of poly-5-nitroindole, and then the poly-5-nitroindole is obtained by purifying by an acetone/water dissolution precipitation method.
Poly-5-nitroindole was added to the ophthalmic lens resin monomer in an amount of 0.1wt% and then cured into a 1mm thick sheet, which was tested for its light absorption effect on the mobile phone screen, recording the blue, yellow and red light absorption ratios.
Example 6
1 part of 5, 6-dimethoxy indole and 1 part of 2, 4-dihydroxybenzophenone 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 poly-5, 6-dimethoxy indole.
Poly (5, 6-dimethoxy indole) is added into an ophthalmic lens resin monomer in an amount of 0.1wt%, and then solidified into a sheet with a thickness of 1mm, and the absorption effect of the sheet on the screen light of the mobile phone is tested, and the absorption proportion of blue light, yellow light and red light is recorded.
The results of the tests of examples 1-6 are as follows:
the results show that poly R-indole is very suitable for use as blue light absorber for blue light resistant ophthalmic lenses. The addition of a small amount of poly R-indole can significantly absorb part of the blue light and has less absorption of yellow and red light.
The polybenzazole prepared in examples 1 to 6 was dissolved in cyclohexane, toluene, methyl methacrylate, ethanol and water, respectively. The dissolution performance was judged qualitatively by comparing the dissolution rate at 0.1% addition and observing the transparency of the solution. Dissolution within 10 seconds of simple shaking and showing orange transparency is marked as excellent (++) in solubility, dissolution within 1 minute of simple shaking and showing orange is marked as good (++), the majority of the solution was dissolved and the orange color of the solution was translucent within 1 minute of sonication, denoted as poor solubility (+), and the majority of the undissolved solution was insoluble within 1 minute of sonication, with the results summarized below:
| solvent(s) | Cyclohexane | Toluene (toluene) | Methyl methacrylate | Ethanol | Water and its preparation method |
| Example 1 | + | ++ | +++ | ++ | - |
| Example 2 | + | ++ | +++ | +++ | + |
| Example 3 | - | ++ | ++ | +++ | - |
| Example 4 | - | ++ | ++ | +++ | ++ |
| Example 5 | - | ++ | +++ | +++ | + |
| Example 6 | ++ | +++ | +++ | ++ | - |
Toluene and ethanol are solvents commonly used in industry, cyclohexane represents a nonpolar solvent, water belongs to a polar solvent, and methyl methacrylate is a polymerizable ester monomer. The results show that the solubility of the polybenzazole has a certain relation with the types of the substituents, and the polybenzazole with proper substituents can be selected according to the principle of similar compatibility when different systems are applied.
The previous description of the embodiments is provided to facilitate a person of ordinary skill in the art in order to make and use the present invention. It will be apparent to those skilled in the art that various modifications can be readily made to these embodiments 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-described embodiments, and those skilled in the art, based on the present disclosure, should make improvements and modifications without departing from the scope of the present invention.
Claims (3)
1. The poly R-indole blue light absorber is characterized by having a structure represented by the following general formula:
wherein n=1 to 6, R represents a substituent attached to a benzene ring, and one substituent attached to a benzene ring is one, R is selected from-CH 3 、-C 2 H 5 、-C(CH 3 ) 3 、-CN、-F、-Cl、-Br、-I、-COOH、-OH、-CH 2 OH、-C 2 H 5 OH、-CH 2 COOH、-NH 2 、-CHO、-NO 2 、-COCH 3 or-CF 3 One or more of the following;
the poly R-indole blue light absorbent is a mixture of series of oligomers obtained from R-indole by a free radical oxidation method; the poly R-indole blue light absorbent has absorption capacity to ultraviolet and short wave blue light wave bands of 400-480nm and has transmission capacity to visible light of more than 500 nm;
the poly R-indole blue light absorber is obtained from indole monomers through a free radical oxidation method;
the indole monomer has a structure represented by the following general formula:
wherein R represents a substituent attached to the benzene ring, and one substituent attached to the benzene ring is one, R is selected from-CH 3 、-C 2 H 5 、-C(CH 3 ) 3 、-CN、-F、-Cl、-Br、-I、-COOH、-OH、-CH 2 OH、-C 2 H 5 OH、-CH 2 COOH、-NH 2 、-CHO、-NO 2 、-COCH 3 or-CF 3 One or more of the following;
the free radical oxidation method is selected from an oxidant oxidation method or an ultraviolet oxidation method;
the steps of the oxidant oxidation method comprise: mixing indole monomers and an oxidant according to the mass ratio of 1 (0.5-5), reacting for 1-168 hours at the temperature of 0-150 ℃, and removing the solvent to obtain the poly R-indole blue light absorbent;
the oxidant is one or more selected from ferric trichloride, potassium dichromate, ammonium persulfate, sodium persulfate, potassium persulfate, sodium percarbonate, ozone, benzoyl peroxide, dicumyl peroxide and isobenzol hydrogen peroxide;
the ultraviolet oxidation method comprises the following steps: uniformly mixing indole monomers, a photoinitiator and a solvent according to the mass ratio of (0.5-5) to (0-500), wherein the solvent dosage is not 0, irradiating for 0.1-24 hours under ultraviolet light, and removing the solvent to obtain the poly R-indole blue light absorbent; the photoinitiator is selected from one or more of benzophenone, 2, 4-dihydroxybenzophenone, 4' -bis (dimethylamino) benzophenone, diphenylethanone, 2-hydroxy-2-methyl-1-phenylpropion or 1-hydroxycyclohexyl phenyl ketone; the wavelength of the ultraviolet light is 250-400nm; 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.
2. The method for preparing the R-indole blue light absorber according to claim 1, wherein the poly R-indole blue light absorber is selected from the group consisting of: one of poly 7-methyl indole formate, poly 5-nitrilo indole, poly 4, 6-difluoro indole, poly 5-amino indole, poly 5-nitro indole or poly 5, 6-dimethoxy indole.
3. The application of the R-indole blue light absorber according to claim 1 or 2, wherein the poly R-indole blue light absorber is used for preparing resin lenses, polymer material films and polymer material coatings.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010616671.6A CN111620885B (en) | 2020-06-30 | 2020-06-30 | Poly R-indole blue light absorber and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010616671.6A CN111620885B (en) | 2020-06-30 | 2020-06-30 | Poly R-indole blue light absorber and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111620885A CN111620885A (en) | 2020-09-04 |
| CN111620885B true CN111620885B (en) | 2023-05-30 |
Family
ID=72269514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010616671.6A Active CN111620885B (en) | 2020-06-30 | 2020-06-30 | Poly R-indole blue light absorber and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111620885B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114031547B (en) * | 2021-11-01 | 2023-05-30 | 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 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003187652A (en) * | 2001-12-21 | 2003-07-04 | Mitsubishi Rayon Co Ltd | Manufacturing method of indole derivative trimer complex conductor |
| JP2003281934A (en) * | 2002-03-20 | 2003-10-03 | Mitsubishi Rayon Co Ltd | Conductive packaging material and container for electronic part molded therefrom |
| CN1660853A (en) * | 2003-12-25 | 2005-08-31 | 伊哈拉化学工业株式会社 | Indolecarboxylic ester trimer and electrochemical cell using the same |
| CN103842338A (en) * | 2011-05-25 | 2014-06-04 | 美洲染料资源公司 | Compounds with oxime ester and/or acyl groups |
| CN105759455A (en) * | 2015-12-31 | 2016-07-13 | 江苏康耐特光学有限公司 | Blue light preventive optical resin lens and preparation method thereof |
| CN108603946A (en) * | 2016-02-08 | 2018-09-28 | 依视路国际公司 | Including the blue light of benzotriazole UV absorbers blocks optical material |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100720628B1 (en) * | 2002-11-01 | 2007-05-21 | 미츠비시 레이온 가부시키가이샤 | Composition containing carbon nanotubes, composite having coating thereof and process for producing them |
-
2020
- 2020-06-30 CN CN202010616671.6A patent/CN111620885B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003187652A (en) * | 2001-12-21 | 2003-07-04 | Mitsubishi Rayon Co Ltd | Manufacturing method of indole derivative trimer complex conductor |
| JP2003281934A (en) * | 2002-03-20 | 2003-10-03 | Mitsubishi Rayon Co Ltd | Conductive packaging material and container for electronic part molded therefrom |
| CN1660853A (en) * | 2003-12-25 | 2005-08-31 | 伊哈拉化学工业株式会社 | Indolecarboxylic ester trimer and electrochemical cell using the same |
| CN103842338A (en) * | 2011-05-25 | 2014-06-04 | 美洲染料资源公司 | Compounds with oxime ester and/or acyl groups |
| CN105759455A (en) * | 2015-12-31 | 2016-07-13 | 江苏康耐特光学有限公司 | Blue light preventive optical resin lens and preparation method thereof |
| CN108603946A (en) * | 2016-02-08 | 2018-09-28 | 依视路国际公司 | Including the blue light of benzotriazole UV absorbers blocks optical material |
Non-Patent Citations (2)
| Title |
|---|
| Electrooxidation of 5-substituted indoles;Peter Jennings等;《J. Chem. Soc., Faraday T rans.》;19970101;第93卷(第21期);第3791页左栏第1行-第3792页右栏第1行，Table 1 * |
| 蓝光有机存储染料研究进展;王雪等;《化学通报》;20091231(第07期);第603-620页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111620885A (en) | 2020-09-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111620885B (en) | Poly R-indole blue light absorber and preparation method and application thereof | |
| KR100812870B1 (en) | Process for producing photochromic layered product | |
| EP0221630A2 (en) | Ultraviolet blocking agents for contact lenses | |
| CN107735416B (en) | Curable composition | |
| CN102712815A (en) | Visible light absorbers for ophthalmic lens materials | |
| CN105008373B (en) | The condensed naphthopyran compounds of substituted 5,6- ring- | |
| EP2980105B1 (en) | Terminal group conversion method and terminal stabilizing method | |
| JP2004504474A (en) | Manufacturing method of photochromic molded product | |
| EP0030968A1 (en) | Irradiation of polyacrylate compositions in air. | |
| EP0639209B1 (en) | Substantially pure synthetic melanin particularly useful for low haze optical devices | |
| JP5484841B2 (en) | Phthalocyanine compounds | |
| EP1312621B1 (en) | Process for producing a photochromic cured product | |
| Allen et al. | Synthesis, characterization and photopolymerization activity of a novel thioxanthone monomer and photopolymers | |
| CN110698676A (en) | Photochromic material, preparation method and contact lens | |
| JP3837037B2 (en) | Coloring composition for color filter, resist composition, and color filter | |
| US3890150A (en) | Photosensitive compositions including aromatic bis-acrylic derivatives | |
| JPH0862841A (en) | Photosensitive resin composition, color filter using the same, and its production | |
| KR101958080B1 (en) | Blue light cut dye and blue light cut sheet comprising the dye | |
| JP2000095950A (en) | Composition for near-infrared absorbing filter and near- infrared absorbing filter made therefrom | |
| AU543067B2 (en) | Poly(ethylenically unsaturated alkoxy) heterocyclic compoundsand crosslinked polymeric coatings | |
| WO2019107026A1 (en) | Fluorine-containing active energy ray-curable resin, liquid repellent agent, resin composition containing same, and cured film | |
| CN115166887B (en) | Antibacterial blue light prevention film for mobile phone and preparation method thereof | |
| JP2021038354A (en) | Resin composition for optical material | |
| Ito et al. | A novel imaging system by dye-sensitized photooxidation of oxazole groups attached to a polymer backbone. 3. Effect of the sensitizer on photooxidation in thin films | |
| JPH0598252A (en) | Photochromic material having polymerizable group and high-molecular photochromic material |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |