CN110950804A - 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compound and synthesis method and application thereof - Google Patents

2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compound and synthesis method and application thereof Download PDF

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CN110950804A
CN110950804A CN201911200630.2A CN201911200630A CN110950804A CN 110950804 A CN110950804 A CN 110950804A CN 201911200630 A CN201911200630 A CN 201911200630A CN 110950804 A CN110950804 A CN 110950804A
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宋森川
麦裕良
史华红
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Guangdong Research Institute Of Petrochemical And Fine Chemical Engineering
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Abstract

The invention discloses a 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compound and a synthesis method and application thereof. The structural formula of the 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compound is shown in the specification
Figure DDA0002295794730000011
Or
Figure DDA0002295794730000012
Wherein R is1Selected from hydrogen, alkyl, alkoxy, halogen or aryl; r2Selected from alkyl groups. The 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compound provided by the invention has the effect of absorbing ultraviolet rays and blue light, so that the compound can be used as an ultraviolet and blue light absorbent, is applied to eye vision optical protective products in the fields of glasses, mobile phones, televisions, computer displays, game machines and the like, absorbs high-energy ultraviolet rays and partial short-wavelength blue light of electronic display screens, and has wide application prospect.

Description

2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compound and synthesis method and application thereof
Technical Field
The invention relates to the technical field of organic materials, in particular to a 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compound and a synthesis method and application thereof.
Background
The us visual commission 2015 digital asthenopia report states: almost all digital products and lighting devices and equipment emit blue light, and the spectrum considered most harmful to retinal cells is light in the wavelength range 415nm to 455nm in the blue-violet color, which accumulates to a certain extent and causes changes in the retina, which can cause problems in visual health, such as the development of age-related macular degeneration and the appearance of cataracts.
Compared with three ultraviolet rays of UV-A, UV-B and UV-C, the proportion of high-energy short-wave blue light reaching retina is larger, and the UV-A ultraviolet light in sunlight and more blue light in visible light can cause phototoxic damage to retina. After irradiation with light, the polyunsaturated fatty acids cause oxidation of photoreceptor cell outer segments, which are shed, and are subsequently phagocytosed by Retinal Pigment Epithelium (RPE), the residual material after digestion by intracellular lysosomes eventually becoming lipofuscin. With age, lipofuscin is produced in large quantities in RPE cells, making RPE cells more vulnerable to phototoxic and oxidative stress. The excessive blue light simultaneously has important influence on the human body physiological time, the coordination and control of the human biological rhythm, the change of the body state in day and night and the like.
At present, display illumination appliances such as illumination lamps used in families and offices, mobile phones, computers, televisions and the like are almost all LED light sources. The time for people to use the electronic products is rapidly increased, and particularly the light energy harm of the high-brightness mobile phone display screen is very prominent. The blue light emitted by such devices is excited by the blue light emitted by the GaM chip (λ p ═ 465nm) to emit yellow light, and the blue light and the yellow light are modulated into white light, so that a higher proportion of blue light exists in the LED backlight. Ultraviolet rays with shorter wavelengths seriously damage human skin and organs. The blue light in the LED backlight source has longer wavelength than ultraviolet light and lower energy than the ultraviolet light, but still has larger irreversible damage to human eyes, especially in the range of 400-460 nm. The electronic products are used by the low-age people in the growth and development period for a long time, the damage degree is larger, and even blindness-causing eye diseases can be induced. Therefore, special light absorbers which absorb high-energy ultraviolet light-blue light and can be applied to the product development in the field of eyesight protection such as glasses, mobile phones, computer screens, televisions and the like are urgently needed in the market.
For ultraviolet or blue light absorbers, such molecules absorb light and then undergo a self energy transition to a high energy level, resulting in poor molecular stability. The molecules are provided with structural units capable of forming intramolecular hydrogen bonds, and when the molecules form the intramolecular hydrogen bonds, energy is released, so that the internal energy of the molecules is reduced, and after the molecules absorb light energy, the energy is improved, so that the intramolecular hydrogen bonds are disconnected; then intramolecular hydrogen bonds are reformed, and energy is released. The process is as follows:
Figure BDA0002295794710000021
therefore, the light absorption process of such molecules is achieved by light energy conversion.
According to the principle that the performance of the ultraviolet absorbent depends on the formation of a six-membered ring in a molecule, the 2- (2-hydroxyphenyl) imidazole or 2- (2-alkoxyphenyl) imidazole compound also has the characteristics of the ultraviolet absorbent. However, few reports are available on the practical application of the compounds.
Disclosure of Invention
In order to overcome the problems in the prior art, the invention aims at providing a 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compound, the invention aims at a synthesis method of the 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compound, and the invention aims at providing an application of the 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compound.
The invention concept of the invention is as follows:
the technical scheme adopted by the invention is as follows: the performance of UV absorbers depends on the principle that six-membered rings can be formed in the molecule, for 2- (2-hydroxyphenyl) imidazoles, 4, 5-diphenyl-2- (2-hydroxyphenyl) imidazoles and 2- (2-hydroxyphenyl) phenanthro [9,10-d ] imidazoles, see the following:
Figure BDA0002295794710000022
by integrating the photophysical properties of 2- (2-hydroxyphenyl) imidazole compounds, 4, 5-diphenyl-2- (2-hydroxyphenyl) imidazole compounds and 2- (2-hydroxyphenyl) phenanthro [9,10-d ] imidazole compounds, the target compound to be developed is set to cover more than 410nm, including ultraviolet and blue light ranges. On the basis of the three types of mixed structures, a conjugated system of a molecular structure is changed, and the following two types of compounds (I and II) are designed and synthesized.
Figure BDA0002295794710000031
The compound is used as an additive material, is combined with other corresponding basic materials to form a composite formula, is expected to be applied to the aspects of mobile phones, televisions, computer displays, blue light protective films or protective glasses of game machines and the like, absorbs high-energy ultraviolet light and part of short-wavelength blue light, and is used for protecting eyesight.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
the invention provides a 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compound, the structural formula of which is shown as formula (I) or formula (II):
Figure BDA0002295794710000032
wherein R is1Selected from hydrogen, alkyl, alkoxy, halogen or aryl; r2Selected from alkyl groups.
The compound represented by the formula (II) means
Figure BDA0002295794710000041
Or
Figure BDA0002295794710000042
Preferably, in formula (I), R1Selected from hydrogen, C1-C6 alkyl or C1-C6 alkoxy; r2Alkyl selected from C1-C6; further preferably, in the formula (I), R1Is tert-butyl, R2Is n-butyl.
Preferably, in the formula (II), R2Alkyl selected from C1-C6; further preferably, in the formula (II), R2Is n-butyl.
The invention provides a synthesis method of a 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compound.
A synthetic method of 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compounds shown in formula (I) comprises the following steps:
1) will be provided with
Figure BDA0002295794710000043
With alkyl halides R2X is reacted to obtain
Figure BDA0002295794710000044
R2Selected from alkyl, X is selected from halogen;
2) will be provided with
Figure BDA0002295794710000045
And
Figure BDA0002295794710000046
reacting to obtain
Figure BDA0002295794710000047
R1Selected from hydrogen, alkyl, alkoxy, halogen or aryl;
3) will be provided with
Figure BDA0002295794710000048
And
Figure BDA0002295794710000049
reacting with ammonium acetate to obtain
Figure BDA00022957947100000410
Specifically, the synthesis method of the compound shown in the formula (I) comprises the following steps: reacting 5-bromo-2-hydroxybenzaldehyde with alkyl halide under the action of alkali, and converting hydroxyl of the 5-bromo-2-hydroxybenzaldehyde into ether; coupling 5-bromo-2-alkoxybenzaldehyde with 4-substituted phenylboronic acid to obtain 2-alkoxy-5 (4-substituted phenyl) benzaldehyde; reacting 2-alkoxy-5 (4-substituted phenyl) benzaldehyde with 9, 10-phenanthrenequinone and ammonium acetate to obtain a target compound I.
Preferably, in step 1) of the process for the synthesis of the compounds of formula (I),
Figure BDA0002295794710000051
with alkyl halides R2The molar ratio of X is 1: (1.2-2); alkyl halides R2X may be selected from bromoalkanes, such as bromobutane; the base used in the reaction with
Figure BDA0002295794710000052
The molar ratio of (1.5-2.5): 1; the reaction condition is 4-6 h at room temperature.
Preferably, in step 2) of the process for the synthesis of the compounds of formula (I),
Figure BDA0002295794710000053
and
Figure BDA0002295794710000054
in a molar ratio of 1: (1.1-1.5); the reaction temperature is 70-90 ℃; the reaction time is 10-15 h.
Preferably, in step 2) of the synthesis method of the compound represented by the formula (I), the reaction is carried out under the action of a base, and the base used can be potassium carbonate. And palladium catalyst is added in the reaction to participate in the reaction, wherein the palladium catalyst can be tetrakis (triphenylphosphine) palladium. The base and the catalyst are suitably used in such amounts as to satisfy the reaction and are common in the art.
Preferably, in step 2) of the synthesis process of the compound of formula (I), the reaction is carried out under a protective atmosphere, for example under a nitrogen atmosphere.
It is preferable thatThe synthesis of the compounds of formula (I) in step 3),
Figure BDA0002295794710000055
and
Figure BDA0002295794710000056
and ammonium acetate in a mass ratio of (1-1.5): 1: (2-3); the reaction temperature is 115-135 ℃; the reaction time is 10-15 h.
A synthetic method of 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compounds shown in formula (II) comprises the following steps:
1) will be provided with
Figure BDA0002295794710000061
With halogenated hydrocarbons R2X is reacted to obtain
Figure BDA0002295794710000062
R2Selected from alkyl, X is selected from halogen;
2) will be provided with
Figure BDA0002295794710000063
And
Figure BDA0002295794710000064
reacting with ammonium acetate to obtain
Figure BDA0002295794710000065
Preferably, the step 2) of the synthesis method of the 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compound shown in the formula (II) is specifically as follows: will be provided with
Figure BDA0002295794710000066
Reacting with 9, 10-phenanthrenequinone and ammonium acetate to obtain
Figure BDA0002295794710000067
Or is to
Figure BDA0002295794710000068
Reacting with 1, 2-diphenylethanedione and ammonium acetate to obtain
Figure BDA0002295794710000069
Specifically, the synthesis method of the compound shown in the formula (II) comprises the following steps: reacting 2-hydroxy naphthalene formaldehyde with alkyl halide under the action of alkali to obtain 2-alkoxy naphthalene formaldehyde; reacting 2-alkoxy naphthaldehyde with 9, 10-phenanthrenequinone (or 1, 2-diphenylethanedione) and ammonium acetate to obtain a target compound II.
Preferably, in step 1) of the process for the synthesis of the compound of formula (II),
Figure BDA00022957947100000610
with alkyl halides R2The molar ratio of X is 1: (1.2-2); alkyl halides R2X may be selected from bromoalkanes, such as bromobutane; the base used in the reaction with
Figure BDA00022957947100000611
The molar ratio of (1.5-2.5): 1; the reaction condition is 4-6 h at room temperature.
Preferably, in step 2) of the process for the synthesis of the compound of formula (II),
Figure BDA0002295794710000071
and
Figure BDA0002295794710000072
and ammonium acetate in a mass ratio of (1-1.5): 1: (2-3); the reaction temperature is 115-135 ℃; the reaction time is 10-15 h.
Figure BDA0002295794710000073
Represents 9, 10-phenanthrenequinone or 1, 2-diphenylethanedione.
The invention also provides application of the 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compound.
The 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compound is applied to the preparation of optical protection products.
Preferably, in this application, the optical protection product is an eye vision protection product for glasses, mobile phones, televisions, computer monitors or game machines. The eye vision protection product can absorb ultraviolet light and partial short-wavelength blue light of the electronic display screen. The eye vision protection product may be a protective film or a protective lens.
The invention provides an ultraviolet-blue light absorbent which comprises the 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compound.
The invention provides an optical resin composition which comprises the 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compound.
Preferably, in the optical resin composition, the mass percent of the 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compounds is 0.3% -3%; more preferably, in the optical resin composition, the mass percentage of the 2- (2-alkoxyphenyl) -4, 5-diphenyl imidazole compound is 0.8-1.2%.
Preferably, such an optical resin composition is a styrene-based resin composition.
Preferably, the optical resin composition is a lens resin material.
Preferably, the optical resin composition comprises the following components in percentage by mass: 78-82% of styrene, 3-5% of cyclopentadiene resin, 1-3% of cyano resin, 0.005-0.015% of light stabilizer, 0.005-0.015% of antioxidant, 0.4-0.8% of release agent, 3-7% of dispersing agent, 0.2-1% of molecular weight regulator, 0.2-1% of curing agent and 0.3-3% of 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compound.
In the optical resin composition, ETERMER 3386 resin can be used as cyclopentadiene resin; the cyanogen-based resin can be ETERMER 2264 resin; the light stabilizer is preferably a light stabilizer UV 770; the antioxidant is preferably antioxidant 264; the release agent is preferably polyethylene oxide release agent, the molecular weight is 200-2000, such as release agent T15; the dispersant is preferably a nano dispersant, such as a nano silicon dispersant.
The invention has the beneficial effects that:
the 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compound provided by the invention has the effects of absorbing ultraviolet (330-.
Specifically, the invention provides synthesis and application of a novel ultraviolet-short wavelength blue light absorber 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole. The method for synthesizing the 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compound is simple, the reaction condition is easy to control, and the separation and purification are easy to implement. The compounds have structural units which are common in ultraviolet absorbers, namely structural units which can form stable intramolecular hydrogen bonds. By virtue of the formation and cleavage of such intramolecular hydrogen bonds, the destructive action of ultraviolet rays can be eliminated, and thus specific stability can be exhibited against violet light; meanwhile, the main light absorption peak is red-shifted by about 10nm compared with common benzotriazole ultraviolet absorbers (UV-P and UV-329), and the main absorption peak is about 360nm, so that the use requirements of certain specific industries can be met. The coverage range of the absorption wavelength of the absorbent reaches 400 nm; when the using amount of the composite material is increased, the coverage range of the absorption wavelength of the composite material is more than 420 nm; has the characteristic of absorbing short-wavelength blue light, and can be applied to various aspects as a blue light absorber. The product can be applied to the eyesight protection products in the fields of glasses, mobile phones, televisions, computer displays, game machines and the like, and has the effect of protecting eyesight.
Drawings
FIG. 1 is an absorption spectrum of Compound 1 in ethyl acetate solution;
FIG. 2 is an absorption spectrum of compound 2 and compound 3 in ethyl acetate solution;
FIG. 3 is an absorption spectrum of compound 2 and compound 3 in a 1, 2-dichloroethane solution.
Detailed Description
The present invention will be described in further detail with reference to specific examples. The starting materials, reagents or apparatus used in the examples were obtained from conventional commercial sources unless otherwise specified. Unless otherwise indicated, the testing or testing methods are conventional in the art.
The following provides three 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compounds, which are compounds 1-3 respectively.
The structural formula of compound 1 is:
Figure BDA0002295794710000091
the structural formula of compound 2 is:
Figure BDA0002295794710000092
the structural formula of compound 3 is:
Figure BDA0002295794710000093
example 1
Synthesis of 2- (4-butoxy-4 '- (tert-butyl) - [1,1' -biphenyl ] -3-yl) phenanthro [9,10-d ] imidazole (Compound 1).
Figure BDA0002295794710000094
Synthesis of 5-bromo-2-alkoxybenzaldehyde from 5-bromo-2-hydroxybenzaldehyde was carried out according to the conventional methods reported in the literature. The references are: liu Jing Zi, Wang Yuliang, Chenshuhua, West south Master university newspaper (Nature science edition), 2005, 30 (2): 301-303; lujie, sourshong leaf, xusonping, university of jiangsu scholars (natural science edition), 2012, 30 (3): 43-46). The reaction of 2-hydroxybenzaldehyde and 1-bromobutane is exemplified here. To 50mL of N, N-dimethylformamide were added 20mmol (4.01g) of 5-bromo-2-hydroxybenzaldehyde, 40mmol (1.60g) of sodium hydroxide and 30mmol (4.11g) of bromobutane, respectively. After stirring at room temperature for 5 hours, the mixture was poured into 500mL of water with stirring, the mixture was extracted with methylene chloride (50 mL. times.3 times), and the obtained organic layer was washed with water (100 mL. times.3 times). After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off to obtain 4.63g of 5-bromo-2-butoxybenzaldehyde as a product in a yield of 90%.
2-butoxy-5- (4-tert-butyl) benzaldehyde is synthesized by referring to coupling reaction literature. Coupling reaction documents are: miyaura, n.; suzuki, A.Chem.Rev.1995,95, 2457-2483; miyaura, n.; suzuki, A.J.chem.Soc.chem.Comm.1979,590, 866-867; suzuki, A.chem.Commun.2005,38, 4759-; suzuki, A.J.organomet.chem.2002,653, 83-90; suzuki, a.; yamamoto, Y.chem.Lett.2011,40, 894-. To a mixture of 80mL of toluene, 16mL of ethanol and 32mL of water were added 10.0mmol (2.57g) of 5-bromo-2-butoxybenzaldehyde, 12.0mmol (2.14g) of 4-tert-butylbenzoic acid, potassium carbonate (5.4g) and tetrakis (triphenylphosphine) palladium (0.40g), respectively. The mixture is treated for 6 times by a method of decompression and nitrogen filling, and the existence of oxygen in the reaction system is ensured. And reacted at 81 ℃ for 12 hours under nitrogen protection. The water was separated and washed with water (50 mL. times.3) to remove sodium carbonate. The solvent was distilled off under reduced pressure, and column separation and purification were carried out to give 2.64g of the objective 5- (4-tert-butylphenyl) -2-butoxybenzaldehyde in a yield of 85%.
Reference imidazole compounds were synthesized. The synthetic imidazoles are described in: xiaoliwei, pengxiaxia, zhouqixiang, kouzwei, shisha, organic chemistry 2015, 35, 1204-; tatami, university of zhongshan university chech, 2006; penhuanan, Zhengdagui, Chenxi, Handazzling, Wuli Dan, Yanyanyangchun, chemical research and application, 2019, 203 and 207. 2.0mmol (0.62g) of 5- (4-tert-butylphenyl) -2-butoxybenzaldehyde, 2.4mmol (0.50g) of 9, 10-phenanthrenequinone, 1.20g of ammonium acetate and 20mL of acetic acid were stirred at 125 ℃ under reflux for 12 hours. After the reaction mixture was cooled, it was slowly poured into 200g of ice water with stirring, allowed to stand, and precipitated for 2 hours. And drying and grinding the solid product obtained by suction filtration, transferring the solid product into 20mL of methanol, stirring, heating to reflux, cooling, and carrying out suction filtration to obtain 0.81g of a target product. The yield was 81% based on 5- (4-tert-butylphenyl) -2-butoxybenzaldehyde.
The results of the nmr measurements of compound 1 are as follows:1H NMR(300MHz,CDCl3)δ:8.92(d,J＝2.4Hz,1H),8.65(d,J＝8.1Hz,2H),7.63(d,J＝8.4Hz,3H),7.59-7.52(m,5H),7.46(d,J＝8.4Hz,3H),6.94(d,J＝8.7Hz,1H),4.14(t,J＝6.6Hz,2H),2.01-1.93(m,2H),1.69-1.62(m,2H),1.39(s,9H)1.11(t,J＝7.2Hz,3H)。13C NMR(75MHz,CDCl3)δ:155.8,150.8,148.2,138.0,135.2,129.3,129.1,128.4,127.7,127.3,126.5,125.9,124.5,118.9,113.3,69.6,35.4,32.5,32.2,20.6,14.7.ESI-MS,m/z499.3[M+H]+。
example 2
Synthesis of 2- (1- (2-butoxynaphthyl)) -4, 5-diphenylimidazole (Compound 2).
Figure BDA0002295794710000111
Referring to the reaction conditions of 5-bromo-2-hydroxybenzaldehyde and bromobutane in example 1, 2-hydroxy-1-naphthaldehyde and 1-bromobutane were reacted to give 2-butoxy-1-naphthaldehyde; referring again to the reaction conditions for synthesizing imidazole compounds from 2-butoxy-5- (4-tert-butyl) benzaldehyde and 9, 10-phenanthrenequinone and ammonium acetate in example 1, 2-butoxy-1-naphthaldehyde and 1, 2-diphenylethanedione and ammonium acetate were synthesized to obtain the objective compound 2, in a yield of 81% based on 2-butoxy-1-naphthaldehyde.
The results of the nmr detection of compound 2 are as follows:1H NMR(300MHz,CDCl3)δ:9.35(d,J＝8.7Hz,1H),8.70(d,J＝7.8Hz,2H),7.81-7.74(m,3H),7.66-7.52(m,7H),7.42-7.39(m,1H),7.23-7.19(m,2H),4.07(t,J＝6.6Hz,2H),1.79-1.69(m,2H),1.48-1.38(m,2H),0.87(t,J＝7.2Hz,3H)。13C NMR(75MHz,CDCl3)δ:155.0,146.0,132.9,131.5,129.7,128.3,128.0,127.7,127.0,126.7,125.1,124.4,123.7,121.8,114.2,112.9,70.0,31.6,19.4,13.8.ESI-MS,m/z 419.2[M+H]+。
example 3
Synthesis of 2- (1- (2-butoxynaphthyl)) -phenanthro [9,10-d ] -imidazole (Compound 3).
Figure BDA0002295794710000112
Referring to example 2, 2-butoxy-1-naphthaldehyde and 9, 10-phenanthrenequinone were combined with ammonium acetate to synthesize the objective compound 3 in a yield of 86% calculated from 2-butoxy-1-naphthaldehyde.
Compound (I)3 the following nuclear magnetic resonance detection results:1H NMR(300MHz,CDCl3)δ:9.48(d,J＝8.7Hz,1H),7.78(J＝9.0Hz,2H),7.64-7.53(m,4H),7.41-7.22(m,7H),4.15(t,J＝6.6Hz,2H),1.82-1.75(m,2H),1.49-1.42(m,2H),0.91(t,J＝7.5Hz,3H)。13C NMR(75MHz,CDCl3)δ:154.4,142.8,132.6,130.7,129.7,128.6,127.9,127.5,127.2,127.0,124.2,114.2,112.7,69.9,31.7,19.5,13.8.ESI-MS,m/z 417.2[M+H]+。
performance testing
And (3) detecting the absorption performance of the 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compound on ultraviolet and blue light.
Compound 1, compound 2 and compound 3 were dissolved in ethyl acetate and 1, 2-dichloroethane, respectively, and their ultraviolet spectrum absorption spectra were tested. FIG. 1 shows the absorption spectrum of Compound 1 in ethyl acetate solution. FIG. 2 shows the absorption spectra of compound 2 and compound 3 in ethyl acetate solution, wherein the concentration of compound 2 is 0.19X 10-5mol/L, concentration of Compound 3 0.17X 10-5mol/L. FIG. 3 is an absorption spectrum of compound 2 and compound 3 in 1, 2-dichloroethane solution, in which the concentration of compound 2 is 0.21X 10-5mol/L, concentration of Compound 3 0.20X 10-5mol/L。
As can be seen from FIG. 3, Compound 3 is present in a solution of 1, 2-dichloroethane at a concentration of about 10-6The absorption wavelength coverage range of the nano-particles exceeds 400nm when the nano-particles are used per liter. If the concentration is increased, the absorption wavelength coverage is shifted to longer wavelengths, even over 420 nm. Therefore, the compounds can be used as long-wavelength ultraviolet and short-wavelength blue light absorbers.
Application example
A resin system comprises the following components in percentage by mass: 80% of styrene, 4% of ETERMER 3386 resin, 2% of ETERMER 2264 resin, 0.01% of UV770 light stabilizer, 0.01% of antioxidant 264, 0.6% of release agent T15, 5% of nano dispersant, 0.5% of molecular weight regulator and 0.5% of curing agent. Adding the compound 3 into a resin system respectively in an adding amount of 1% by mass, stirring uniformly, and transferring into a mold. The oven was heated to 90 c and the mold with the sample was placed in the oven and programmed to a temperature of 130 c at a rate of 1 c per minute and then held for 20 hours to cure. And then naturally cooling to room temperature, and demolding to obtain the lens. The cut-off wavelength of the product obtained was 415nm as determined by UV absorptiometry.
The 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compound provided by the invention is used as an ultraviolet-blue light absorbent, can be applied to the aspects of blue light protective films or protective glasses of mobile phones, televisions, computer monitors, game machines and the like, and can absorb high-energy ultraviolet light and part of short-wavelength blue light so as to protect eyesight.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.

Claims (10)

  1. A2- (2-alkoxyphenyl) -4, 5-diphenyl imidazole compound has a structural formula shown in formula (I) or formula (II):
    Figure FDA0002295794700000011
    wherein R is1Selected from hydrogen, alkyl, alkoxy, halogen or aryl; r2Selected from alkyl groups.
  2. 2. The 2- (2-alkoxyphenyl) -4, 5-diphenylimidazole compounds according to claim 1, characterized in that: in the formula (I), R1Selected from hydrogen, C1-C6 alkyl or C1-C6 alkoxy; r2Is selected from alkyl of C1-C6.
  3. 3. The 2- (2-alkoxyphenyl) -4, 5-diphenylimidazole compounds according to claim 1, characterized in that: in the formula (II), R2Is selected from alkyl of C1-C6.
  4. 4. A process for the synthesis of 2- (2-alkoxyphenyl) -4, 5-diphenylimidazoles of formula (i) as claimed in claim 1, characterized in that: the method comprises the following steps:
    1) will be provided with
    Figure FDA0002295794700000012
    With alkyl halides R2X is reacted to obtain
    Figure FDA0002295794700000013
    R2Selected from alkyl, X is selected from halogen;
    2) will be provided with
    Figure FDA0002295794700000014
    Reacting to obtain
    Figure FDA0002295794700000015
    R1Selected from hydrogen, alkyl, alkoxy, halogen or aryl;
    3) will be provided with
    Figure FDA0002295794700000016
    Reacting with ammonium acetate to obtain
    Figure FDA0002295794700000021
  5. 5. A method for synthesizing 2- (2-alkoxyphenyl) -4, 5-diphenyl imidazole compounds shown in formula (ii) of claim 1, which is characterized in that: the method comprises the following steps:
    1) will be provided with
    Figure FDA0002295794700000022
    With halogenated hydrocarbons R2X is reacted to obtain
    Figure FDA0002295794700000023
    R2Selected from alkyl, X is selected from halogen;
    2) will be provided with
    Figure FDA0002295794700000024
    Reacting with ammonium acetate to obtain
    Figure FDA0002295794700000025
  6. 6. The method of synthesis according to claim 5, characterized in that: the step 2) is specifically as follows: will be provided with
    Figure FDA0002295794700000026
    9, 10-phenanthrenequinone reacts with ammonium acetate to obtain
    Figure FDA0002295794700000027
    Or is to
    Figure FDA0002295794700000028
    Reacting with 1, 2-diphenylethanedione and ammonium acetate to obtain
    Figure FDA0002295794700000029
  7. 7. The use of 2- (2-alkoxyphenyl) -4, 5-diphenylimidazoles as claimed in claim 1 for the preparation of optical protection products.
  8. 8. Use according to claim 7, characterized in that: the optical protection product is an eye vision protection product of glasses, a mobile phone, a television, a computer display or a game machine.
  9. 9. An ultraviolet-blue light absorber characterized by: comprising the 2- (2-alkoxyphenyl) -4, 5-diphenylimidazole compound of claim 1.
  10. 10. An optical resin composition characterized by: comprising the 2- (2-alkoxyphenyl) -4, 5-diphenylimidazole compound of claim 1.
CN201911200630.2A 2019-11-29 2019-11-29 2- (2-alkoxy phenyl) -4, 5-diphenyl imidazole compound and synthesis method and application thereof Pending CN110950804A (en)

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