CN115724777A - Blue light absorption material, preparation method and application - Google Patents
Blue light absorption material, preparation method and application Download PDFInfo
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- CN115724777A CN115724777A CN202210913791.1A CN202210913791A CN115724777A CN 115724777 A CN115724777 A CN 115724777A CN 202210913791 A CN202210913791 A CN 202210913791A CN 115724777 A CN115724777 A CN 115724777A
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- blue light
- light absorption
- absorbing material
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- 239000000463 material Substances 0.000 title claims abstract description 62
- 230000031700 light absorption Effects 0.000 title claims abstract description 52
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- -1 phenylamino, piperidyl Chemical group 0.000 claims abstract description 43
- 238000002156 mixing Methods 0.000 claims abstract description 33
- 239000003960 organic solvent Substances 0.000 claims abstract description 23
- 239000002994 raw material Substances 0.000 claims abstract description 22
- 238000006467 substitution reaction Methods 0.000 claims abstract description 20
- 150000001412 amines Chemical class 0.000 claims abstract description 14
- 238000005935 nucleophilic addition reaction Methods 0.000 claims abstract description 11
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 8
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims abstract description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims abstract description 5
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- 238000000034 method Methods 0.000 claims description 30
- 239000011358 absorbing material Substances 0.000 claims description 23
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
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- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 claims description 7
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 5
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- REWALGMGSNYLOK-UHFFFAOYSA-N octyl 2-(benzenesulfonyl)acetate Chemical compound CCCCCCCCOC(=O)CS(=O)(=O)C1=CC=CC=C1 REWALGMGSNYLOK-UHFFFAOYSA-N 0.000 claims description 3
- 230000002265 prevention Effects 0.000 abstract description 21
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- 238000006243 chemical reaction Methods 0.000 description 30
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
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- 238000004440 column chromatography Methods 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- CHLCPTJLUJHDBO-UHFFFAOYSA-M sodium;benzenesulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CC=C1 CHLCPTJLUJHDBO-UHFFFAOYSA-M 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
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- VSTXCZGEEVFJES-UHFFFAOYSA-N 1-cycloundecyl-1,5-diazacycloundec-5-ene Chemical compound C1CCCCCC(CCCC1)N1CCCCCC=NCCC1 VSTXCZGEEVFJES-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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- 125000004185 ester group Chemical group 0.000 description 2
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- IJDHTIMWHATBKH-UHFFFAOYSA-N octan-2-yl 2-chloroacetate Chemical compound CCCCCCC(C)OC(=O)CCl IJDHTIMWHATBKH-UHFFFAOYSA-N 0.000 description 2
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
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- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
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- NNXMXUSTTDFBDE-UHFFFAOYSA-N octyl 2-chloroacetate Chemical compound CCCCCCCCOC(=O)CCl NNXMXUSTTDFBDE-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a blue light absorption material, a preparation method and application thereof, and the blue light absorption material has structures shown in a formula I and a formula II:
in the formula II, R comprises phenylamino, piperidyl or morpholinyl; the preparation method comprises the following steps: mixing benzene sulfonyl ester, amine raw materials, an alkaline reagent and an organic solvent, and carrying out nucleophilic addition and substitution reaction to obtain a blue light absorption material; or mixing benzene sulfonyl ester, amine raw material and organic solvent for substitution reaction to obtain blueAnd (3) light absorption materials, so as to obtain the blue light absorption materials. The blue light absorption material provided by the invention can be directly doped into a lens base material, does not influence the thickness of a blue light prevention lens, and has an excellent light absorption effect of high-energy short-wave blue light.
Description
Technical Field
The invention belongs to the technical field of organic light absorption materials, and relates to a blue light absorption material, and a preparation method and application thereof.
Background
With the development of modern technologies, a series of electronic products flood the lives and works of people, such as mobile phones, computers, panels, televisions and the like. A large amount of blue light is reserved in artificial light sources of screens of the electronic products, short-wave blue light (415-455 nm) with high energy can penetrate through crystalline lenses and reach retinas, absorption peaks of retinas in blue light areas exist in retinas in human eyes, free radicals can be generated when the retinas are irradiated by the long-term blue light, and the free radicals can cause retinal pigment epithelial cells to die down, so that various ophthalmic diseases such as retinopathy and the like are caused. Blocking blue light from irradiating for a long time is the most effective method for reducing blue light harm, and the blue light prevention lens can effectively solve the problem. However, most of the existing blue light-proof lenses are covered with a blue light-proof layer on the surface of the lens substrate, for example, covered with an inorganic composite oxide layer, which results in an excessively thick blue light-proof lens.
Disclosure of Invention
The invention aims to overcome the defects in the prior art, and provides a blue light absorption material, a preparation method and application thereof, which can be directly doped into a lens base material, does not influence the thickness of a blue light prevention lens, and has an excellent light absorption effect of high-energy short-wave blue light.
In order to achieve the purpose, the invention is realized by adopting the following technical scheme:
a blue light absorption material has a structure shown in formula I and formula II:
in the formula II, R comprises phenylamino, piperidyl or morpholinyl.
A preparation method of a blue light absorption material comprises the following steps:
mixing benzene sulfonyl ester, amine raw materials, an alkaline reagent and an organic solvent, and carrying out nucleophilic addition and substitution reaction to obtain a blue light absorption material;
or mixing benzene sulfonyl ester, amine raw materials and an organic solvent, and carrying out substitution reaction to obtain a blue light absorption material;
the amine raw material comprises N-ethyl ethylamine salt, N- ((1E, 2E) -3- (phenylamino) allyl) chloroaniline, piperidine or morpholine.
Optionally, the molar ratio of the benzene sulfonyl ester to the amine raw material is 1 (1.2-1.5).
Optionally, the molar ratio of the benzenesulfonyl ester to the alkaline reagent is 1: (2-6).
Optionally, the benzenesulfonyl ester comprises octyl 2- (benzenesulfonyl) acetate, octyl 2- ((4-methoxyphenyl) sulfonyl) acetate, or octyl (2e, 4e) -5- (N-phenylacetamido) -2- (benzenesulfonyl) -2, 4-dienoate.
Optionally, the organic solvent comprises N, N-dimethylacetamide, acetonitrile, methanol, ethyl acetate, or tetrahydrofuran.
Optionally, the temperature of the nucleophilic addition reaction is 25-35 ℃, and the time is 11-14 h; the temperature of the substitution reaction is 75-85 ℃ and the time is 1-3 h.
The invention provides an application of the blue light absorption material in the technical scheme or the blue light absorption material prepared by the preparation method in the technical scheme in a blue light prevention lens.
Optionally, the blue light prevention lens comprises a lens base material and a blue light absorption material doped in the lens base material; the blue light absorption material is the blue light absorption material prepared by the technical scheme or the blue light absorption material prepared by the preparation method of the technical scheme.
Optionally, the doping amount of the blue light absorption material is 0.2 to 1 wt%.
Compared with the prior art, the invention has the following beneficial effects:
the blue light absorption material provided by the invention has a sulfone structure, and the sulfone structure is used as an electron-donating and-withdrawing group, so that intramolecular charge transfer can be promoted, and electrons in molecules of the blue light absorption material can flow, so that light absorption is realized; the ester group with conjugation ability and small steric hindrance has weak electron-withdrawing ability, and the introduction of the ester group can effectively adjust the charge transfer in molecules, so that high-energy short-wave blue light harmful to human eyes can be effectively absorbed, and the color requirement of people cannot be influenced; moreover, the light absorption material provided by the invention can be directly doped into the lens base material, the thickness of the blue light prevention lens is not influenced, the blue light transmittance and blue light blocking ratio of the blue light prevention lens containing the blue light absorption material provided by the invention are high, and the blue light prevention effect is good;
the preparation method of the blue light absorption material provided by the invention is simple to operate, low in preparation raw material cost and suitable for industrial production;
the invention provides an application of a blue light absorbing material in a blue light prevention lens, and the blue light prevention lens has high blue light transmittance and blue light blocking ratio and good blue light prevention effect.
Drawings
FIG. 1 is a UV-VIS spectrum of a solid blue light absorbing material prepared in example 1;
FIG. 2 is a graph of the blue light blocking lens prepared in example 1 and the corresponding transmittance results;
FIG. 3 is a chart of the UV-VIS absorption spectrum of the solid blue light absorbing material prepared in example 2;
FIG. 4 is a graph of the blue light blocking lens prepared in example 2 and the corresponding transmittance results;
FIG. 5 is a UV-VIS spectrum of a solid blue light absorbing material prepared in example 3;
FIG. 6 is a graph of the blue light blocking lens prepared in example 3 and the corresponding transmittance results;
FIG. 7 is a chart of the UV-VIS absorption spectrum of the solid blue light absorbing material prepared in example 4;
fig. 8 is a graph of the blue light blocking lens prepared in example 4 and the corresponding transmittance results.
Detailed Description
The invention is further described below with reference to the accompanying drawings. The following examples are only for illustrating the technical solutions of the present invention more clearly, and the protection scope of the present invention is not limited thereby.
The endpoints of the ranges and any values disclosed herein are not limited to the precise range or value, and such ranges or values should be understood to encompass values close to those ranges or values. For ranges of values, between the endpoints of each of the ranges and the individual points, and between the individual points may be combined with each other to give one or more new ranges of values, and these ranges of values should be considered as specifically disclosed herein.
For the purposes of the present specification and appended claims, unless otherwise indicated, all numbers expressing quantities, percentages or proportions, and other numerical values used in the specification and appended claims, are to be understood as being modified in all instances by the term "about". Moreover, all ranges disclosed herein are inclusive of the endpoints and independently combinable.
A blue light absorbing material has a structure represented by formula I and formula II:
in the formula II, R comprises phenylamino, piperidyl or morpholinyl.
In the invention, the blue light absorption material has a structure shown in any one of formulas I-1 and II-1 to II-3:
the invention provides a preparation method of the blue light absorption material in the technical scheme, which comprises the following steps:
mixing benzene sulfonyl ester, amine raw materials, an alkaline reagent and an organic solvent, and carrying out nucleophilic addition and substitution reaction;
or mixing the benzene sulfonyl ester, the amine raw material and the organic solvent, and carrying out substitution reaction to obtain the blue light absorption material with the structures shown in the formula I and the formula II.
In the present invention, all the raw material components are commercially available products well known to those skilled in the art unless otherwise specified.
In the present invention, the benzenesulfonyl ester comprises octyl 2- (benzenesulfonyl) acetate
Octyl 2- ((4-methoxyphenyl) sulfonyl) acetate
Or octyl (2E, 4E) -5- (N-phenylacetamido) -2- (phenylsulfonyl) -2, 4-dienoate
The amine raw material comprises N-ethyl ethylamine salt
N- ((1E, 2E) -3- (phenylamino) allyl) chloroaniline
Piperidine derivatives
Or morpholine
In the present invention, the molar ratio of the benzenesulfonyl ester to the amine-based raw material is preferably 1 (1 to 2), more preferably 1 (1.2 to 1.8), and most preferably 1 (1.4 to 1.6).
In the present invention, the piperidine and morpholine are preferably commercially available.
In the invention, the preparation method of the 2- (benzenesulfonyl) octyl acetate comprises the following steps: mixing sodium benzene sulfinate, 2-octyl chloroacetate and an organic solvent at room temperature, and carrying out substitution reaction to obtain 2- (benzenesulfonyl) octyl acetate. The organic solvent preferably comprises N, N-dimethylformamide, methanol, ethyl acetate or tetrahydrofuran. In the present invention, the molar ratio of the sodium benzene sulfinate to the octyl 2-chloroacetate is preferably 1 (1-2), more preferably 1; the amount of the organic solvent used in the present invention is not particularly limited, and sodium benzene sulfinate can be dissolved, and in a specific embodiment of the present invention, the ratio of the mass of the sodium benzene sulfinate to the volume of the N, N-dimethylformamide solvent is preferably 1g:50mL. In the invention, the mixing mode is preferably stirring mixing, the speed and time of stirring mixing are not particularly limited, and the raw materials can be uniformly mixed; the mixing order is preferably that sodium benzene sulfinate and 2-octyl chloroacetate are mixed and then mixed with the organic solvent. In the present invention, the temperature of the substitution reaction is preferably 20 to 35 ℃, more preferably 25 to 30 ℃; the time of the substitution reaction is preferably 2 to 8 hours, and more preferably 4 to 6 hours; the substitution reaction process is carried out according to the following reaction formula (1):
after the substitution reaction, the method preferably further comprises the steps of extracting the reaction liquid of the substitution reaction, and sequentially washing, drying, concentrating and separating and purifying by column chromatography to obtain the 2- (benzenesulfonyl) octyl acetate. In the present invention, the extractant used for the extraction preferably comprises ethyl acetate or dichloromethane; the use of the extractant in the extraction process can avoid the loss of the reaction liquid during transfer. In the present invention, the washing is preferably a saturated sodium chloride solution washing for the purpose of removing water-soluble impurities in the reaction liquid. In the present invention, the drying means is preferably drying with a drying agent, and the drying agent preferably includes anhydrous sodium sulfate or anhydrous magnesium sulfate. The concentration method of the present invention is not particularly limited, and the solvent can be removed by a concentration method known to those skilled in the art, such as distillation under reduced pressure. In the invention, the eluent used for column chromatography separation and purification is preferably a mixed eluent of petroleum ether and ethyl acetate or a mixed eluent of petroleum ether and dichloromethane, and the volume ratio of petroleum ether to ethyl acetate in the mixed eluent of petroleum ether and ethyl acetate is preferably (10-20): 1, more preferably (5-15): 1, and most preferably 10; the volume ratio of the petroleum ether to the dichloromethane in the mixed eluent of the petroleum ether and the dichloromethane is preferably (10-20): 1, more preferably (5-15): 1, and most preferably 10.
In the present invention, the preparation method of the octyl 2- ((4-methoxyphenyl) sulfonyl) acetate is preferably the same as the preparation method of the octyl 2- (phenylsulfonyl) acetate in the above technical solution, the preparation conditions of the octyl 2- (phenylsulfonyl) acetate are different in that sodium benzene sulfinate is replaced by sodium p-methoxybenzenesulfite, and other preparation conditions are the same as the preparation conditions of the octyl 2- (phenylsulfonyl) acetate, and therefore, the description thereof is omitted. In the invention, in the preparation process of the octyl 2- ((4-methoxyphenyl) sulfonyl) acetate, the reaction generated in the substitution reaction process is as shown in formula (2):
in the present invention, a method for preparing octyl (2e, 4e) -5- (N-phenylacetamido) -2- (phenylsulfonyl) -2, 4-dienoate, comprises the following steps: under the conditions of low temperature and protective atmosphere, (2E, 4E) -5- (phenylamino) -2- (phenylsulfonyl) penta-2, 4-dienoic acid octyl ester, acetyl chloride and an organic solvent are mixed and subjected to substitution reaction to obtain (2E, 4E) -5- (N-phenylacetylamino) -2- (phenylsulfonyl) -2, 4-dienoic acid octyl ester. The organic solvent preferably comprises dichloromethane, methanol, ethyl acetate or tetrahydrofuran; the protective atmosphere preferably comprises nitrogen, argon or helium. In the present invention, the molar ratio of octyl (2E, 4E) -5- (phenylamino) -2- (phenylsulfonyl) penta-2, 4-dienoate to acetyl chloride is preferably 1 (1-2), more preferably 1.2; the amount of the organic solvent used in the present invention is not particularly limited, and octyl (2e, 4e) -5- (phenylamino) -2- (phenylsulfonyl) penta-2, 4-dienoate may be dissolved, and in specific examples of the present invention, the ratio of the mass of octyl (2e, 4e) -5- (phenylamino) -2- (phenylsulfonyl) penta-2, 4-dienoate to the volume of the dichloromethane solvent is preferably 1g:30mL. In the invention, the mixing mode is preferably stirring mixing, the speed and time of stirring mixing are not particularly limited, and the raw materials can be uniformly mixed; the mixing order is preferably that acetyl chloride and the organic solvent are mixed and then mixed with octyl (2E, 4E) -5- (phenylamino) -2- (phenylsulfonyl) penta-2, 4-dienoate. In the present invention, the temperature of the substitution reaction is preferably-20 to-3 ℃, more preferably-15 to-5 ℃; the time of the substitution reaction is preferably 4 to 8 hours, and more preferably 3 to 5 hours; the reaction occurring during the substitution reaction is as shown in formula (3):
after the substitution reaction, the invention preferably also comprises the steps of extracting the reaction liquid of the reaction, and sequentially washing, drying and concentrating the obtained organic phase to obtain the octyl (2E, 4E) -5- (N-phenylacetamido) -2- (benzenesulfonyl) -2, 4-dienoate. In the present invention, the extractant used for the extraction preferably comprises ethyl acetate or dichloromethane; the use of the extractant in the extraction process can avoid the loss of the reaction liquid during transfer. In the present invention, the washing is preferably a saturated sodium chloride solution washing for the purpose of removing water-soluble impurities in the reaction liquid. In the present invention, the drying means is preferably drying with a drying agent, and the drying agent preferably includes anhydrous sodium sulfate or anhydrous magnesium sulfate. The concentration method of the present invention is not particularly limited, and the solvent can be removed by a concentration method known to those skilled in the art, such as distillation under reduced pressure.
In the present invention, the method for preparing the N-ethyl ethylamine salt preferably comprises the following steps: 1, 3-tetramethoxypropane, diethylamine and acetic acid are mixed and reacted to obtain N-ethyl ethylamine salt.
In the present invention, the molar ratio of the 1, 3-tetramethoxypropane to diethylamine is preferably 1 (1 to 2), more preferably 1; in a specific embodiment of the present invention, the ratio of the mass of the 1, 3-tetramethoxypropane to the volume of the acetic acid solvent is preferably 1g:40mL. In the invention, the mixing mode is preferably stirring mixing, the speed and time of stirring mixing are not particularly limited, and the raw materials can be uniformly mixed; the mixing order is preferably that 1, 3-tetramethoxypropane and diethylamine are mixed and then mixed with acetic acid solvent. In the present invention, the temperature of the reaction is preferably 120 to 145 ℃, more preferably 130 to 140 ℃; the reaction time is preferably 4 to 9 hours, and more preferably 5 to 7 hours; the reaction process has the reaction shown as the formula (4):
after the reaction, the method preferably further comprises the steps of extracting the reaction liquid of the reaction, and washing, drying and concentrating the obtained organic phase in sequence to obtain the N-ethyl ethylamine salt. In the present invention, the extractant used for the extraction preferably comprises ethyl acetate or dichloromethane; the use of the extractant in the extraction process can avoid the loss of the reaction liquid during transfer. In the present invention, the washing is preferably a saturated sodium chloride solution washing for the purpose of removing water-soluble impurities in the reaction liquid. In the present invention, the drying means is preferably drying with a drying agent, and the drying agent preferably includes anhydrous sodium sulfate or anhydrous magnesium sulfate. The present invention is not particularly limited in the manner of concentration, and the solvent can be removed by a concentration method known to those skilled in the art, such as distillation under reduced pressure.
In the present invention, the method for producing N- ((1e, 2e) -3- (phenylamino) allyl) chloroaniline preferably comprises the following steps: mixing 1, 3-tetramethoxypropane, aniline and an organic solvent at low temperature, and reacting to obtain N- ((1E, 2E) -3- (phenylamino) allyl) chloroaniline. The organic solvent preferably comprises ethanol or methanol. In the present invention, the molar ratio of the 1, 3-tetramethoxypropane to the aniline is preferably 1 (2 to 3), more preferably 1; the amount of the organic solvent used in the present invention is not particularly limited, and 1, 3-tetramethoxypropane can be dissolved, and in a specific embodiment of the present invention, the ratio of the mass of the 1, 3-tetramethoxypropane to the volume of the ethanol solvent is preferably 1g:50mL. In the invention, the mixing mode is preferably stirring mixing, the speed and time of stirring mixing are not particularly limited, and the raw materials can be uniformly mixed; the mixing order is preferably that 1, 3-tetramethoxypropane and aniline are mixed and then mixed with an organic solvent, and then hydrochloric acid is slowly dropped. In the present invention, the temperature of the reaction is preferably 20 to 35 ℃, more preferably 25 to 30 ℃; the reaction time is preferably 1 to 5 hours, and more preferably 2 to 4 hours; the reaction process takes place as shown in formula (5):
after the reaction, the invention preferably further comprises washing and drying the solid obtained by the reaction in sequence to obtain the N- ((1E, 2E) -3- (phenylamino) allyl) chloroaniline. In the present invention, the washing is preferably water washing for the purpose of removing hydrochloric acid and water-soluble impurities which may remain in the reaction solution. In the present invention, the drying method is preferably drying in a vacuum oven.
In the present invention, the basic reagent preferably comprises 1, 8-diazabicycloundec-7-ene or pyridine; the molar ratio of the benzenesulfonyl ester raw material to the alkaline reagent is 1: (2 to 6), more preferably 1: (3.5 to 5), most preferably 1: (4-4.5). The organic solvent comprises N, N-dimethylacetamide, methanol, N-dimethylformamide and tetrahydrofuran.
In the present invention, the mixing method is preferably stirring mixing, and the speed and time of stirring mixing are not particularly limited, and the raw materials may be uniformly mixed.
In the present invention, the temperature of the nucleophilic addition reaction is preferably 20 to 40 ℃, more preferably 25 to 35 ℃; the time of the nucleophilic addition reaction is preferably 10 to 16 hours, and more preferably 11 to 14 hours; the temperature for the substitution reaction is preferably 75 to 85 ℃, and more preferably 78 to 82 ℃; the substitution reaction time is preferably 4 to 8 hours, more preferably 3 to 5 hours. The reaction generated in the nucleophilic addition and substitution reaction process is shown as the formula (6):
wherein R comprises piperidinyl or morpholinyl.
After the nucleophilic addition and substitution reactions, the method preferably further comprises the steps of extracting reaction liquid of the nucleophilic addition and substitution reactions, and sequentially washing, drying, concentrating and purifying by column chromatography to obtain the blue light absorption materials with the structures shown in the formulas I and II.
In the present invention, the extractant for the extraction preferably comprises ethyl acetate or dichloromethane. In the present invention, the washing is preferably a saturated sodium chloride solution washing for the purpose of removing water-soluble impurities in the reaction liquid. In the present invention, the drying means is preferably drying with a drying agent, and the drying agent preferably includes anhydrous sodium sulfate or anhydrous magnesium sulfate. The concentration method of the present invention is not particularly limited, and the solvent can be removed by a concentration method known to those skilled in the art, such as distillation under reduced pressure. In the present invention, the eluent used for the column chromatography separation and purification is preferably a mixed eluent of petroleum ether and ethyl acetate or a mixed eluent of petroleum ether and dichloromethane, and the volume ratio of petroleum ether to ethyl acetate in the mixed eluent of petroleum ether and ethyl acetate is preferably (6-10): 1, more preferably (4-8): 1, and most preferably (3-6): 1; the volume ratio of the petroleum ether to the dichloromethane in the mixed eluent of the petroleum ether and the dichloromethane is preferably (5-30): 1, more preferably (10-20): 1, and most preferably (15-20): 1.
The invention provides an application of the blue light absorption material in the technical scheme or the blue light absorption material prepared by the preparation method in the technical scheme in a blue light prevention lens, wherein the blue light prevention lens comprises a lens base material and the blue light absorption material doped in the lens base material;
the blue light absorption material is the blue light absorption material in the technical scheme or the blue light absorption material prepared by the preparation method in the technical scheme.
The material of the lens base material is not particularly limited, and the lens base material known by the person skilled in the art can be adopted; in a specific embodiment of the present invention, the monomer of the lens substrate is preferably KR-54 epoxy resin. In the present invention, the doping amount of the blue light absorption material is preferably 0.2 to 1 wt%, more preferably 0.4 to 0.8 wt%, and most preferably 0.5 to 0.6 wt%. In the invention, the wavelength of blue light which can be absorbed by the blue light prevention lens is preferably 300-430 nm.
In the invention, the components of the blue light prevention lens further comprise a light curing agent and a coloring agent; the light curing agent is preferably ESACUREONE, and the mass ratio of the monomer to the light curing agent of the lens base material is preferably 1: (0.01 to 0.025), more preferably 1; the coloring agent is preferably a coloring agent B51, and the mass ratio of the monomer to the coloring agent of the lens base material is preferably 1: (0.001 to 0.0025), and more preferably 1.
In the present invention, the method for preparing the blue light prevention lens preferably comprises the following steps: and mixing the blue light absorption material and the monomer of the lens base material, and then carrying out ultraviolet curing to obtain the blue light prevention lens.
In the invention, when the components of the blue light prevention lens further include a light curing agent and a coloring agent, the blue light absorption material, the monomer of the lens base material, the light curing agent and the coloring agent are preferably mixed and then subjected to ultraviolet light curing to obtain the blue light prevention lens. In the invention, the mixture is subjected to ultraviolet curing after mixing, preferably, the mixture obtained by mixing is added into a reaction beaker, a reaction bottle is stirred by a digital display reinforcement stirrer in the air atmosphere, and an electronic intelligent temperature controller is used for stirring the reaction for 2 hours at room temperature to obtain a block copolymer; and (3) placing the segmented copolymer under an ultraviolet light source for ultraviolet curing to obtain the blue-light-proof lens. In the present invention, the stirring speed is preferably 500 to 650r/min, more preferably 550 to 600r/min, and the stirring time is preferably 110 to 125min, more preferably 115 to 120min. In the present invention, the block copolymer is preferably subjected to a vacuum evacuation treatment before being subjected to ultraviolet curing; the degree of vacuum after evacuation is preferably 0.45 to 0.6Pa, more preferably 0.5 to 0.55Pa. In the invention, the ultraviolet light source is preferably a high-pressure ultraviolet mercury lamp, the wavelength of light of the high-pressure ultraviolet mercury lamp is preferably 365nm, and the power of the high-pressure ultraviolet mercury lamp is preferably 800-1000W, and more preferably 900W; the distance between the block copolymer and the ultraviolet light source is preferably 4-5.5 cm, and more preferably 4.5-5 cm; the block copolymer is preferably placed in a mold, preferably quartz glass or ordinary glass; the present invention preferably moves the block copolymer placed in the mold to a space from the ultraviolet light source by conveying; the invention preferably carries out ultraviolet curing after the ultraviolet light source is stabilized. In the invention, the ultraviolet curing is preferably performed by turning over the block copolymer after one surface of the block copolymer is subjected to first ultraviolet curing, then performing second ultraviolet curing on the other surface of the block copolymer, and repeating the first ultraviolet curing and the second ultraviolet curing until the block copolymer is completely cured; the time of the first ultraviolet light curing is preferably 0.6-1.2 min, and more preferably 0.8-1 min; the time of the second ultraviolet curing is preferably 0.8-1.2 min, and more preferably 1min; the number of repetition is not particularly limited, and the block copolymer can be completely cured; the complete cure is preferably determined by visual inspection and slight shaking of the mold to block the copolymer from flowing. By adopting the ultraviolet curing mode, the two surfaces of the blue-light-proof lens can be irradiated by ultraviolet light, and the curing effect of the blue-light-proof lens can be prevented from being influenced by heat energy. After the ultraviolet curing, the invention preferably also comprises the step of demoulding the ultraviolet cured product to obtain the blue-light-proof lens; the demolding method is not particularly limited, and demolding methods known to those skilled in the art can be used.
The technical solution of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. It should be apparent that the described embodiments are only some embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The first embodiment is as follows:
after 2- ((4-methoxyphenyl) sulfonyl) acetic acid octyl ester (2.00g, 5.80mmol), N-ethyl ethylamine salt (1.68g, 6.96mmol) and N, N-dimethylacetamide (30 mL) were stirred and mixed uniformly, 1, 8-diazabicycloundec-7-ene (5.29g, 34.80mmol) was slowly added and stirred at 30 ℃ for reaction for 12 hours, and then the resulting reaction solution was extracted with ethyl acetate, and the resulting organic phase was washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate in sequence, and then ethyl acetate was removed by distillation under reduced pressure, and the resulting concentrate was subjected to column chromatography for purification, with an eluent being a petroleum ether-ethyl acetate mixed eluent (petroleum ether: ethyl acetate volume ratio = 5), to obtain a blue light-absorbing material having a structure represented by formula i-1 (abbreviated as TX1, white solid, yield 61.4%).
Nuclear magnetic data of TX 1: 1 HNMR(400MHz,CDCl 3 -d 6 )δ7.97(d,J＝12.6Hz,1H),7.82(d,J＝8.8Hz,2H),7.14(d,J＝12.5Hz,1H),6.90(d,J＝8.8Hz,2H),6.49(t,J＝12.5Hz,1H),4.04(t,J＝6.7Hz,2H),3.84(s,3H),3.37(q,J＝7.1Hz,4H),1.56–1.43(m,2H),1.36–1.12(m,16H),0.88(t,J＝6.8Hz,3H). 13 CNMR(101MHz,CDCl 3 -d 6 )δ164.02,162.31,157.91,154.75,135.30,129.84,113.48,111.68,97.10,64.29,55.58,50.95,43.45,31.94,29.43,29.28,28.73,26.09,22.75,14.74,14.21,11.96。
testing of ultraviolet-visible absorption spectrum: under the condition of room temperature, using Agilent8453 type ultraviolet visible light photometer to make ultraviolet absorption spectrum scanning in 200-800 nm waveband, and measuring concentration is 1X 10 -5 The ultraviolet-visible absorption spectrum (UV) of a dichloromethane solution of TX1 in mol/L is shown in FIG. 1. As can be seen from FIG. 1, TX1 shows a strong absorption peak at 310-410 nm, which indicates that the solid blue light absorbing material with the structure shown in formula I-1 can absorb short-wave blue light.
Preparing the blue-light-proof lens: mixing TX1 (0.2 g), resin KR-54 (200.00 g), a light curing agent ESACUREONE (4.0 g) and a coloring agent B51 (0.4 g) and adding into a reaction beaker, stirring a reaction bottle by using a digital display booster stirrer in an air atmosphere at the rotating speed of 600r/min, stirring the reaction bottle at room temperature for 2h by using an electronic intelligent thermometer to obtain a block copolymer, vacuumizing, turning on a high-pressure ultraviolet mercury lamp with the light wavelength of 365nm and the power of 900W, moving a mold filled with the copolymer to a position 5cm away from a light source through a conveyor belt when the light source is stable, starting timing, performing first ultraviolet curing on one surface of the block copolymer for 1min, turning the mold over, performing second ultraviolet curing on the other surface of the block copolymer for 1min, and repeating the first ultraviolet curing-second ultraviolet curing operation to enable both surfaces of the lens to be subjected to ultraviolet irradiation so as to prevent the influence of heat energy on a curing experiment; demolding after complete curing is determined by visual observation and slight shaking of the mold to obtain the blue-light-proof lens; wherein the addition amount of TX1 is 0.2 wt%, the UV value is 406nm, and the transmittance of the blue-light-proof lens is shown in figure 2.
The second embodiment:
after 2- (benzenesulfonyl) acetic acid octyl ester (5.00g, 16.00mmol), N- ((1e, 2e) -3- (phenylamino) allyl) chloroaniline (5.34g, 20.80mmol) and N, N-dimethylacetamide (50 mL) were uniformly mixed with stirring, 1, 8-diazabicycloundec-7-ene (4.87g, 32.00mmol) was slowly added and reacted at 30 ℃ with stirring, then the resulting reaction solution was extracted with ethyl acetate, the resulting organic phase was washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate in this order, ethyl acetate was removed by distillation under reduced pressure, and the resulting concentrate was subjected to column chromatography for purification, with an eluent of a petroleum ether-ethyl acetate mixture (petroleum ether: ethyl acetate volume ratio = 5), to obtain a blue light absorbing material having a structure represented by formula ii-1 (abbreviated as TX2, yellow powder, yield 62.3%).
Nuclear magnetic data of TX 2: 1 HNMR(400MHz,CDCl 3 -d 6 )δ8.12(d,J＝12.3Hz,1H),7.91(d,J＝7.4Hz,2H),7.64(t,J＝13.0Hz,1H),7.53(t,J＝7.2Hz,1H),7.47(t,J＝7.4Hz,2H),7.38(t,J＝7.9Hz,2H),7.21(d,J＝13.6Hz,1H),7.13(t,J＝7.4Hz,1H),7.02(d,J＝8.0Hz,2H),6.95(t,J＝12.5Hz,1H),4.03(t,J＝6.7Hz,2H),1.46(dt,J＝14.2,7.0Hz,2H),1.33–1.12(m,10H),0.88(t,J＝7.0Hz,3H). 13 CNMR(101MHz,CDCl 3 -d 6 )δ163.40,154.16,149.54,142.66,139.28,132.34,130.07,128.57,127.81,124.35,116.87,116.50,102.60,65.00,31.93,29.34,29.26,28.52,25.90,22.78,14.24。
testing of ultraviolet-visible absorption spectrum: under the condition of room temperature, using Agilent8453 type ultraviolet visible light photometer to make ultraviolet absorption spectrum scanning in 200-800 nm waveband, and measuring concentration is 1X 10 -5 The ultraviolet-visible absorption spectrum of the TX2 dichloromethane solution of mol/L and the test result are shown in the figure 3. From FIG. 3, TX2 shows a strong absorption peak at 330-450 nm.
Preparing a blue-light-proof lens: a blue light prevention lens was manufactured according to the method of example 1, which is different from example 1 in that TX1 was replaced with TX2, wherein the amount of TX2 added was 1 wt%, the UV value was 445nm, and the transmittance of the blue light prevention lens is shown in fig. 4. As can be seen from fig. 3 and 4, the blue light absorber prepared in this example has a good light absorption effect.
Example three:
after (2E, 4E) -5- (N-phenylacetamido) -2- (benzenesulfonyl) -2, 4-dienoic acid octyl ester (1.70g, 3.50mmol), piperidine (0.42g, 4.90mmol) and acetonitrile (30 mL) are stirred and mixed uniformly, the reaction is stirred and refluxed for 2 hours, after the reaction is finished, the reaction solution is cooled to room temperature naturally, 4mL of isopropanol and 20mL of water are added, a solid is precipitated, and the blue light absorbing material with the structure shown in formula II-2 is obtained by suction filtration (abbreviated as TX3, white powder and yield of 60.3%).
Nuclear magnetic data of TX 3: 1 HNMR(400MHz,CDCl 3 -d 6 )δ8.00(d,J＝12.6Hz,1H),7.87(d,J＝8.2Hz,2H),7.48(t,J＝7.0Hz,1H),7.42(t,J＝7.3Hz,2H),7.13(d,J＝12.4Hz,1H),6.59(t,J＝12.5Hz,1H),4.00(t,J＝6.6Hz,2H),3.43(t,J＝5.3Hz,4H),1.78–1.60(m,6H),1.43(p,J＝6.7Hz,2H),1.31–1.09(m,10H),0.88(t,J＝6.9Hz,3H). 13 CNMR(101MHz,CDCl 3 -d 6 )δ164.04,158.67,155.47,143.62,131.78,128.33,127.58,110.68,96.63,64.30,55.75,46.84,31.94,29.40,29.27,28.67,26.69,26.03,25.16,23.97,22.78,14.24。
testing of ultraviolet-visible absorption spectrum: under the condition of room temperature, using Agilent8453 type ultraviolet visible light photometer to make ultraviolet absorption spectrum scanning in 200-800 nm waveband, and measuring concentration is 1X 10 -5 The ultraviolet-visible absorption spectrum of the TX3 dichloromethane solution in mol/L shows the test result as shown in figure 3. As can be seen from FIG. 5, TX3 shows a strong absorption peak at 310-410 nm.
Preparing a blue-light-proof lens: a blue light-proof lens was manufactured according to the method of example 1, which is different from example 1 in that TX1 was replaced with TX3, wherein the addition amount of TX3 was 1 wt%, the UV value was 406nm, and the transmittance of the blue light-proof lens is shown in fig. 6. As can be seen from fig. 6, the light absorption effect of the blue light absorber prepared in this embodiment is closer to that of TX 1.
Example four:
after (2E, 4E) -5- (N-phenylacetamido) -2- (benzenesulfonyl) -2, 4-dienoic acid octyl ester (0.50g, 1.00mmol), morpholine (0.125g, 1.50mmol) and acetonitrile (20 mL) are stirred and mixed uniformly, the reaction is stirred and refluxed for 2h, after the reaction is finished, the reaction is naturally cooled to room temperature, then 4mL of isopropanol and 20mL of water are added, a solid is precipitated, and the blue light absorbing material with the structure shown in the formula II-3 is obtained by suction filtration (abbreviated as TX4, white powder and yield of 65.4%).
Nuclear magnetic data of TX 4: 1 HNMR(400MHz,CDCl 3 -d 6 )δ8.02(d,J＝12.5Hz,1H),7.87(d,J＝7.9Hz,2H),7.50(t,J＝7.4Hz,1H),7.44(t,J＝7.5Hz,2H),7.11(d,J＝12.6Hz,1H),6.60(t,J＝12.5Hz,1H),4.00(t,J＝6.6Hz,2H),3.77(t,J＝5.0Hz,4H),3.46(t,J＝5.0Hz,4H),1.43(p,J＝6.8Hz,2H),1.31–1.08(m,10H),0.88(t,J＝6.9Hz,3H). 13 CNMR(101MHz,DMSO-d 6 )δ162.96,160.43,154.61,143.61,131.86,128.54,126.78,108.78,96.06,63.28,52.96,45.74,31.22,28.64,28.60,28.11,25.42,22.09,13.98。
testing of ultraviolet-visible absorption spectrum: at room temperature, scanning ultraviolet absorption spectrum with Agilent8453 type ultraviolet-visible spectrophotometer at 200-800 nm to obtain 1 × 10 concentration -5 The ultraviolet-visible absorption spectrum of the TX4 dichloromethane solution of mol/L and the test result are shown in figure 3. As can be seen from FIG. 7, TX4 shows a strong absorption peak at 310-420 nm.
Preparing the blue-light-proof lens: a blue light-proof lens was manufactured according to the method of example 1, which is different from example 1 in that TX1 was replaced with TX4, wherein the addition amount of TX4 was 1 wt%, the UV value was 411nm, and the transmittance of the blue light-proof lens is shown in fig. 8. As can be seen from fig. 8, the light absorption effect of the blue light absorber prepared in this embodiment is closer to that of TX 1.
The above description is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, it is possible to make various improvements and modifications without departing from the technical principle of the present invention, and those improvements and modifications should be considered as the protection scope of the present invention.
Claims (10)
1. A blue light absorption material is characterized by having structures shown in formula I and formula II:
in the formula II, R comprises phenylamino, piperidyl or morpholinyl.
2. A method of preparing a blue-light absorbing material according to claim 1, comprising the steps of:
mixing benzene sulfonyl ester, amine raw materials, an alkaline reagent and an organic solvent, and carrying out nucleophilic addition and substitution reaction to obtain a blue light absorption material;
or mixing benzene sulfonyl ester, amine raw materials and an organic solvent, and carrying out substitution reaction to obtain a blue light absorption material;
the amine raw material comprises N-ethyl ethylamine salt, N- ((1E, 2E) -3- (phenylamino) allyl) chloroaniline, piperidine or morpholine.
3. The method of claim 2, wherein the blue light absorbing material comprises: the molar ratio of the benzene sulfonyl ester to the amine raw material is 1 (1.2-1.5).
4. The method for preparing a blue light absorbing material according to claim 2, wherein: the molar ratio of the benzenesulfonyl ester to the alkaline reagent is 1: (2-6).
5. The method of claim 2, wherein the blue light absorbing material comprises: the benzenesulfonyl ester comprises octyl 2- (benzenesulfonyl) acetate, octyl 2- ((4-methoxyphenyl) sulfonyl) acetate or octyl (2E, 4E) -5- (N-phenylacetamido) -2- (benzenesulfonyl) -2, 4-dienoate.
6. The method of claim 2, wherein the blue light absorbing material comprises: the organic solvent comprises N, N-dimethylacetamide, acetonitrile, methanol, ethyl acetate or tetrahydrofuran.
7. The method for preparing a blue light absorbing material according to claim 2, wherein: the temperature of the nucleophilic addition reaction is 25-35 ℃, and the time is 11-14 h; the temperature of the substitution reaction is 75-85 ℃ and the time is 1-3 h.
8. Use of the blue light absorbing material according to claim 1 or the blue light absorbing material prepared by the method according to any one of claims 2 to 7 in a blue light blocking lens.
9. The use of a blue light absorbing material according to claim 8 in a blue light blocking lens, wherein: the blue-light-proof lens comprises a lens base material and a blue-light-absorbing material doped in the lens base material; the blue light absorption material is prepared by the blue light absorption material of claim 1 or the preparation method of the blue light absorption material of any one of claims 2 to 7.
10. The use of the blue light absorbing material in a blue light blocking lens according to claim 9, wherein the amount of the blue light absorbing material is 0.2 to 1 wt%.
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| CN113582890A (en) * | 2021-06-24 | 2021-11-02 | 南京傅立叶生物医药科技有限公司 | Cyanine modified compound, intermediate, preparation method and application thereof |
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