CN114031547A - Indole compound and application thereof - Google Patents
Indole compound and application thereof Download PDFInfo
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Abstract
The invention discloses an indole compound which has the following structural general formula:
wherein R is1Selected from hydrogen, C1～C8Straight chain alkyl group of (1), C1～C8An alkyl group having a branched chain,
R3Selected from hydrogen, methyl, ethyl, methoxy, ethoxy; r2Selected from hydrogen, C1～C8Straight chain alkyl group of (1), C1～C8An alkyl group containing a branch. The indole compound is adopted in the blue light prevention substrate lens, the blue light prevention effect is remarkable, the addition amount of the blue light absorbent is greatly reduced, and various physical properties of the lens are basically not influenced.
Description
Technical Field
The invention belongs to the technical field of materials for lenses, and particularly relates to an indole compound and application thereof in preparation of lenses.
Background
In 2010, smart phones, tablets, computers and the like gradually enter people's lives, various mobile phone APPs and the like occupy a large amount of fragmentization time of people, and the change can generate huge burden on eyes of people. Generally, the screen of the electronic device continuously emits harmful blue light radiation, wherein the high-energy short-wave blue light with the wavelength of 380-450 nm has a permanent damage risk to the retina. The blue light radiation has strong penetrating power and can penetrate through crystalline lens to directly reach retina, thereby causing macular degeneration of retina, aggravating chromatic aberration and blurred vision, finally destroying hormone secretion balance and influencing vision and sleep quality, and various problems and hidden troubles caused by the blue light radiation are more obvious. Therefore, various technologies for preventing and treating harmful blue light have been advanced in recent years. Especially various prevent blue light screen, prevent blue membrane and prevent blue light glasses technique, the accessible reduces smart machine and plays the guard action to the blue light of transmitting to people's eye, reduces harm.
The common blue light prevention technology is to reduce the blue light transmittance by adding one or more blue light absorbers, and the common blue light absorbers comprise yellow toner, blue toner, orange toner and nano Al2O3Polyacrylic acid mixture and nano TiO2Polyacrylic acid mixture, nano Fe2O3Polyacrylic acid mixture, metal complex dye, benzotriazole compound, PMMA polymethacrylic acid, fullerene and the like. Among these absorbers, the image toner has the defects of dark background color, low light transmittance and obvious influence on daily use of people; the problems of complex manufacturing process and high preparation cost of the nano inorganic material exist; the remaining classes of absorbers suffer from the disadvantage that the blue light protection effect is not significant.
Therefore, the development of the organic blue light absorber which is low in cost, easy to industrially produce, high in efficiency and long in service life has obvious commercial value when being applied to blue light prevention lenses and blue light prevention films.
Disclosure of Invention
The first purpose of the invention is to provide an indole compound.
The second purpose of the invention is to provide an application of the indole compound in preparing a blue light absorber.
The third purpose of the invention is to provide the application of the indole compound in preparing a blue light-proof substrate lens.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
the first aspect of the invention provides an indole compound having the following structural formula:
wherein R is1Selected from hydrogen, C1～C8Straight chain alkyl group of (1), C1～C8An alkyl group having a branched chain,
R3Selected from hydrogen, methyl, ethyl, methoxy, ethoxy;
R2selected from hydrogen, C1～C8Straight chain alkyl group of (1), C1～C8An alkyl group containing a branch.
More preferably, in the indole compound, R1Selected from hydrogen, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl,
R3Selected from hydrogen, methyl, ethyl, methoxy, ethoxy;
R2selected from hydrogen, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl.
Most preferably, the structure of the indole compound is selected from one of the following structures:
the second aspect of the invention provides an application of the indole compound in preparing a blue-light absorber.
The third aspect of the invention provides a blue-light-proof substrate lens which is prepared from the following components in parts by weight: 25-75 parts of monofunctional group reaction monomer, 25-75 parts of polyfunctional group reaction monomer and 0-10 parts of oligomer, and adding an initiator and a blue light absorbent, wherein the adding amount of the initiator accounts for 0.1-0.15% of the total mass of the monofunctional group reaction monomer, the polyfunctional group reaction monomer, the oligomer, the initiator and the blue light absorbent, and the adding amount of the blue light absorbent accounts for 0.01-0.15% of the total mass of the monofunctional group reaction monomer, the polyfunctional group reaction monomer, the oligomer, the initiator and the blue light absorbent.
The oligomer is preferably 1,2,3, 4-10 parts.
Preferably, the blue light prevention substrate lens is prepared from the following components in parts by weight: 50-75 parts of monofunctional group reaction monomer, 25-45 parts of polyfunctional group reaction monomer and 5-10 parts of oligomer, and adding an initiator and a blue light absorbent, wherein the adding amount of the initiator accounts for 0.1% of the total mass of the monofunctional group reaction monomer, the polyfunctional group reaction monomer, the oligomer, the initiator and the blue light absorbent, and the adding amount of the blue light absorbent accounts for 0.1% of the total mass of the monofunctional group reaction monomer, the polyfunctional group reaction monomer, the oligomer, the initiator and the blue light absorbent.
The monofunctional reactive monomer is selected from styrene, methacrylic acid, acrylic acid, methylstyrene, butyl acrylate, isooctyl acrylate, ethyl methacrylate, cyclohexyl acrylate, benzyl acrylate, ethoxylated nonylphenol acrylate, hydroxyethyl acrylate, o-phenylphenoxyethyl acrylate, tetrahydrofurfuryl acrylate, and the like.
The multifunctional reactive monomer is selected from dipropylene glycol diacrylate, tripropylene glycol diacrylate, polyethylene glycol diacrylate, ethoxylated bisphenol A diacrylate, polyethylene glycol dimethacrylate, propoxylated glycerol triacrylate, pentaerythritol tetraacrylate, ethoxylated pentaerythritol tetraacrylate and the like.
The oligomer is selected from aliphatic urethane acrylate oligomer, aromatic urethane acrylate, epoxy acrylate, bisphenol a epoxy acrylate, polyester acrylate, and the like.
The initiator is selected from diisopropyl peroxydicarbonate, dicyclohexyl peroxydicarbonate, benzoyl peroxide, dicumyl peroxide, tert-butyl peroxybenzoate, azobisisobutyronitrile and azobisisoheptonitrile.
The blue light absorbent is the indole compound.
The preparation method of the blue light prevention substrate lens comprises the following steps:
step one, uniformly mixing a monofunctional group reaction monomer, a polyfunctional group reaction monomer, an oligomer and a blue light absorbent, adding an initiator, vacuumizing for 10-60 min at room temperature, controlling the temperature to be 35-50 ℃, standing and vacuumizing for 10-60 min;
secondly, filtering the uniformly mixed mixture prepared in the first step, injecting the mixture into a mold for sealing, and carrying out programmed temperature rise to 95 ℃ from room temperature in a curing furnace for 20 hours to finish primary curing to obtain a lens;
temperature programmed curve: keeping the temperature for 0-5h at 34 ℃; uniformly rising the temperature to 50 ℃ within 5-12 h; ③ rising to 95 ℃ at a constant speed for 12-18 h; fourthly, keeping the temperature for 18 to 20 hours at 95 ℃;
and thirdly, performing die sinking, edge cutting and cleaning procedures on the lens obtained in the second step, and performing secondary curing molding at a constant temperature of 105-115 ℃ for 1-2 hours to obtain the blue light-proof substrate lens.
Due to the adoption of the technical scheme, the invention has the following advantages and beneficial effects:
the indole compound is adopted in the blue light prevention substrate lens, the blue light prevention effect is remarkable, the addition amount of the blue light absorbent is greatly reduced, and various physical properties of the lens are basically not influenced.
The blue-blocking substrate lens of the present invention has a lower yellowness index under the same test conditions (note that the yellowness index values measured by the apparatus of the present invention are all somewhat higher, internally measured values, and thus are internally parallel compared).
The blue light-proof substrate lens has yellowing resistance, and the yellow index does not change after long-time illumination.
Drawings
FIG. 1 is a graph showing the absorbance of THF solutions (1% by mass fraction) of compound I-1 and compound I-2.
Detailed Description
In order to more clearly illustrate the invention, the invention is further described below in connection with preferred embodiments. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and is not to be taken as limiting the scope of the invention.
The room temperature in the following examples means (20 ℃ C. to 30 ℃ C.).
The organic solvents used in the present invention, such as anhydrous Tetrahydrofuran (THF), N-Dimethylformamide (DMF) and ethanol, are purchased from Aladdin, 1,2,3,3a,4,8 b-hexahydrocyclopenta [ b ] indole is purchased from Beijing Bailingwei science and technology Co., Ltd, and other reagents are purchased from Sigma-Aldrich.
The yellow index and cut-off wavelength testing instrument is an Agilent Cary 60 type ultraviolet-visible spectrophotometer, the falling ball impact resistance is a BMC-B1 type falling ball impact testing machine of Labthink, and the anti-aging performance testing instrument is a Q-SUN Xe-1 type Xenon Test Chamber of Q-LAB.
Example 1
In the first step, the dried compound of formula (II) (15.9g, 0.1mol) was dissolved in bromoethane (10.9g, 0.1mol)Into 230mL of anhydrous tetrahydrofuran was charged a dry four-necked flask, stirred at room temperature for 2 hours, poured into a large amount of water, extracted with dichloromethane (100mL), washed with water five times (5X 100mL), combined with the organic phase, and passed through Na2SO4Drying, filtration, spin drying of the organic phase, column chromatography using 2/8 ethyl acetate/n-hexane as eluent gave product (IIIa) as an off-white solid. NMR showed that the product had a structure corresponding to 4-ethyl-1, 2,3,3a,4,8 b-hexahydrocyclopenta [ b ] group]Indoles are identical in structure. HRMS (ESI, M/z) [ M + H ]]+calcd for(C13H17N),188.1434；found,188.1336。
Secondly, the compound (IIIa) (18.7g, 0.1mol) prepared in the first step, phosphorus oxychloride (3.06g, 0.02mmol) and DMF (73g, 1.0mol) are put into a 500mL three-neck flask, reacted for 6 hours at room temperature, the solvent is removed by spinning, and column chromatography is carried out after spinning drying [ 200-300 mesh silica gel]Separating and purifying, and eluting with petroleum ether and dichloromethane in a volume ratio of 1:1 to obtain the solid compound (IVa). NMR showed that the product had a structure corresponding to 4-ethyl-1, 2,3,3a,4,8 b-hexahydrocyclopenta [ b ] group]Indole-7-carbaldehyde has a consistent structure. HRMS (ESI, M/z) [ M + H ]]+calcd for(C14H17NO),216.1383；found,216.1397。
Third, compound (IVa) (21.5g, 0.1mol) and cyanoacetic acid (6.72g, 0.08mol) were put into a 500mL two-necked flask, and ammonium acetate (3.1g, 0.04mol), acetic acid (3.6g, 0.06mol) and 200mL of toluene were added thereto, reacted at 130 ℃ and refluxed for three hours. And cooling to room temperature, precipitating a yellow solid, performing suction filtration, and leaching a filter cake with an ethanol solution to obtain a yellow solid compound (Va). NMR showed the product to have a structure similar to (E) -2-cyano-3- (4-ethyl-1, 2,3,3a,4,8 b-hexahydrocyclopenta [ b ] b]Indol-7-yl) acrylic acid. HRMS (ESI, M/z) [ M + H ]]+calcd for(C17H18N2O2),283.1441；found,283.1485。
In the fourth step, compound (Va) (28.2g, 0.1mol) and ethanol (18.4g, 0.4mol) were put into a 500mL two-necked flask, followed by addition of methanesulfonic acid (9.6g, 0.1mol) and 100mL of toluene, reaction at 120 ℃ and reflux for three hours. Cooling to room temperature, adding deionized water for washing, evaporating the solvent to dryness, adding 100ml of alcohol, precipitating yellow crystals, performing suction filtration, and leaching a filter cake by using an ethanol solution to obtain a target compound I-1.1H NMR(500MHz,CDCl3)δ6.68-7.84(m,4H),3.39-4.33(q,4H),2.74-3.02(t,2H),1.12-1.93(m,12H).HRMS(ESI,m/z):[M+H]+calcd for(C19H22N2O2),311.1754；found,311.1745。
Example 2
In the first step, the dried compound represented by the formula (II) (15.9g, 0.1mol) and p-bromoanisole (18.7g, 0.1mol) were dissolved in 230mL of anhydrous tetrahydrofuran, and the resulting solution was charged into a dry four-necked flask, stirred at room temperature for 2 hours, poured into a large amount of water, extracted with dichloromethane (100mL), washed with water five times (5X 100mL), combined with the organic phase, and Na-washed2SO4Drying, filtering and spin-drying the organic phase to obtain an oily product (IIIb) for the next reaction. NMR showed the product to have a chemical bond with 4- (4-methoxyphenyl) -1,2,3,3a,4,8 b-hexahydrocyclopenta [ b]Indoles are identical in structure. HRMS (ESI, M/z) [ M + H ]]+calcd for(C18H19NO),266.1539；found,266.1579。
In a second step, compound (IIIb) prepared in the first step (26.5g,0.1mol), phosphorus oxychloride (3.06g, 0.02mmol) and DMF (73g, 1.0mol) at room temperature for 6 hours, removing the solvent by spinning, and performing column chromatography on silica gel with 200-300 meshes after spinning drying]And eluting with petroleum ether and dichloromethane in a volume ratio of 1:1 to obtain the solid compound (IVb). NMR showed the product to have a chemical bond with 4- (4-methoxyphenyl) -1,2,3,3a,4,8 b-hexahydrocyclopenta [ b]Indole-7-carbaldehyde has a consistent structure. HRMS (ESI, M/z) [ M + H ]]+calcd for(C19H19NO2),294.1489；found,294.1476。
Third, compound (IVb) (29.3g, 0.1mol) and cyanoacetic acid (6.72g, 0.08mol) were put into a 500mL two-necked flask, and ammonium acetate (3.1g, 0.04mol), acetic acid (3.6g, 0.06mol) and 100mL of toluene were added thereto, reacted at 130 ℃ and refluxed for three hours. And cooling to room temperature, precipitating yellow solid, performing suction filtration, and leaching a filter cake by using an ethanol solution to obtain a yellow solid compound (Vb). NMR showed the product to have a structure similar to (E) -2-cyano-3- (4- (4-methoxyphenyl) -1,2,3,3a,4,8 b-hexahydrocyclopenta [ b ] b]Indol-7-yl) acrylic acid. HRMS (ESI, M/z) [ M + H ]]+calcd for(C22H20N2O3),361.1547；found,361.1433。
In the fourth step, compound (Vb) (36.0g, 0.1mol) and ethanol (18.4g, 0.4mol) were put into a 500mL two-necked flask, followed by addition of trifluoromethanesulfonic acid (15.0g, 0.1mol) and 100mL of toluene, reaction at 120 ℃ and reflux for three hours. Cooling to room temperature, adding deionized water, washing for 5 times (5 × 100mL), evaporating to remove solvent, adding 100mL alcohol to precipitate yellow crystal, vacuum filtering, and recrystallizing the filter cake with ethanol to obtain target solid compound I-2.1H NMR(500MHz,CDCl3)δ6.79-7.88(m,8H),4.43(q,2H),2.74-3.81(m,5H),1.29-1.93(m,9H).HRMS(ESI,m/z):[M+H]+calcd for(C24H24N2O3),389.1860；found,389.1745。
And (3) effect testing: the results of dissolving and diluting compound I-10.1g and I-20.1g in 10mL of THF respectively and measuring the absorbance by a UV spectrophotometer are shown in FIG. 1, and FIG. 1 is a graph showing the absorbance of THF solutions (1% by mass fraction) of compound I-1 and compound I-2. As can be seen from FIG. 1, both Compound I-1 and Compound I-2 have good absorption of light at wavelengths below 425 nm.
Example 3
Compound I-3 was obtained by substituting bromoisopropane for the bromoethane used in the first reaction step of example 1, and the other steps and reagents used were the same as in example 1.1H NMR(500MHz,CDCl3)δ8.23(S,1H)6.68-7.14(m,3H),3.39-4.33(q,3H),2.74-3.02(t,2H),1.12-1.93(m,15H).HRMS(ESI,m/z):[M+H]+calcd for(C20H24N2O2),325.1911；found,325.1945。
Example 4
Compound I-4 was obtained by substituting t-butanol for ethanol used in the fourth reaction step of example 2 and the other steps and reagents used were the same as in example 2.1H NMR(500MHz,CDCl3)δ6.79-7.88(m,8H),4.14(s,3H),2.74-3.81(m,2H),1.29-1.93(m,15H).HRMS(ESI,m/z):[M+H]+calcd for(C26H28N2O3),417.2173；found,417.2205。
Example 5
An indole compound prepared based on examples 1-4 is used as a blue light absorbent for manufacturing a casting type blue light-proof substrate lens, and is prepared from the following components in parts by weight in table 1:
TABLE 1
The amount of azobisisobutyronitrile added as an initiator was 0.1% by mass of the total amount of the monofunctional group-reactive monomer, the polyfunctional group-reactive monomer, the oligomer, the initiator and the blue light absorber (0.1 part in this example), and the amount of the blue light absorber compound I-1 was 0.1% by mass of the total amount of the monofunctional group-reactive monomer, the polyfunctional group-reactive monomer, the oligomer, the initiator and the blue light absorber (0.1 part in this example).
The preparation method of the blue light prevention substrate lens comprises the following steps:
firstly, uniformly mixing a monofunctional group reaction monomer, a polyfunctional group reaction monomer, an oligomer and a blue light absorber, adding the mixture into a conical flask, stirring for 1 hour, adding an initiator, vacuumizing for 30 minutes at room temperature, and continuously stirring and uniformly mixing in the process. Then controlling the temperature at 40 ℃, stirring at the speed of 300r/min, standing and vacuumizing for 30 minutes.
Second, the uniformly mixed mixture prepared in the first step was filtered through a 1.0 μm filter, injected into a glass mold (Jiangsu Atai optics Co., Ltd., lens mold), sealed, and temperature-programmed from room temperature to 95 ℃ over 20 hours in a curing oven, temperature-programmed curve: keeping the temperature for 0-5h at 34 ℃; uniformly rising the temperature to 50 ℃ within 5-12 h; ③ rising to 95 ℃ at a constant speed for 12-18 h; fourthly, keeping the temperature for 18 to 20 hours at 95 ℃; completing one curing to obtain the lens.
And thirdly, performing die sinking, edge cutting and cleaning procedures on the lens obtained in the second step, and performing secondary curing molding in a precise curing furnace at the constant temperature of 110 ℃ for 1.5 hours to obtain the blue light-proof substrate lens.
And fourthly, detecting the yellow index YI (obtained according to a yellow index calculation method recommended by ASTM E313 or HG/T3862-2006, wherein the calculation formula is YI-100 (CxX-CzZ)/Y, wherein X, Y, Z is a CIE tri-stimulus value, Cx and Cz are coefficients, Cx-1.28 and Cz-1.06 are values in the experiment, the UV cut-off wavelength (the wavelength with the transmittance reaching 98 percent is taken as a value), the falling ball impact resistance (the falling ball impact test is tested according to national standard QB/T2506-.
Example 6
An indole compound prepared based on examples 1-4 is used as a blue light absorbent for manufacturing a casting type blue light-proof substrate lens, and is prepared from the following components in parts by weight in table 2:
TABLE 2
| Composition (I) | Parts by weight | |
| Monofunctional reactive monomer | Methyl styrene | 50 portions of |
| Polyfunctional reactive monomer | Ethoxylated bisphenol A diacrylate | 40 portions of |
| Oligomer | Polyester acrylate | 10 portions of |
The amount of azobisisoheptonitrile added as an initiator was 0.1% of the total mass of the monofunctional group-reactive monomer, the polyfunctional group-reactive monomer, the oligomer, the initiator and the blue light absorber (0.1 part in this example), the amount of the blue light absorber compound I-1 was 0.05% of the total mass of the monofunctional group-reactive monomer, the polyfunctional group-reactive monomer, the oligomer, the initiator and the blue light absorber (0.05 part in this example), and the amount of the blue light absorber compound I-2 was 0.05% of the total mass of the monofunctional group-reactive monomer, the polyfunctional group-reactive monomer, the oligomer, the initiator and the blue light absorber (0.05 part in this example).
The preparation method is the same as example 5.
Example 7
An indole compound prepared based on examples 1-4 is used as a blue light absorbent for manufacturing a casting type blue light-proof substrate lens, and is prepared from the following components in parts by weight in table 3:
TABLE 3
The amount of azobisisobutyronitrile as an initiator added was 0.1% of the total mass of the monofunctional group-reactive monomer, the polyfunctional group-reactive monomer, the oligomer, the initiator and the blue light absorber (0.1 part in this example), the amount of the blue light absorber compound I-3 was 0.05% of the total mass of the monofunctional group-reactive monomer, the polyfunctional group-reactive monomer, the oligomer, the initiator and the blue light absorber (0.05 part in this example), and the amount of the blue light absorber compound I-4 was 0.05% of the total mass of the monofunctional group-reactive monomer, the polyfunctional group-reactive monomer, the oligomer, the initiator and the blue light absorber (0.05 part in this example).
The preparation method is the same as example 5.
Comparative example 1
The substrate lens prepared in the prior art comprises the following specific components in parts by weight:
TABLE 4
The amount of azobisisobutyronitrile added as an initiator was 0.1% by mass of the total amount of the monofunctional group-reactive monomer, the polyfunctional group-reactive monomer, the oligomer and the initiator (0.1 part in this example).
The preparation process is the same as example 5, commonly called white tablet, and the difference in the preparation process is that no blue light absorbent is added in the formula.
Comparative example 2
The substrate lens prepared in the prior art comprises the following specific components in parts by weight:
TABLE 5
| Composition (I) | Parts by weight | |
| Monofunctional reactive monomer | Methyl styrene | 50 portions of |
| Polyfunctional reactive monomer | Ethoxylated bisphenol A diacrylate | 40 portions of |
| Oligomer | Polyester acrylate | 10 portions of |
The amount of azobisisoheptonitrile added as an initiator was 0.1% of the total mass of the monofunctional reactive monomer, the polyfunctional reactive monomer, the oligomer and the initiator (in this example, 0.1 part by weight). The amount of the ultraviolet absorber UV326 added was 1% of the total mass of the monofunctional reactive monomer, polyfunctional reactive monomer, oligomer and initiator (in this example, 1 part was added).
The manufacturing process is the same as the production process of the blue light-proof substrate in the embodiment 5, the temperature programming condition is the same, and the formula is different.
The performance of the substrate lenses prepared in examples 5-7 and comparative examples 1 and 2 were tested according to the criteria given in example 5, with the results shown in table 6:
TABLE 6
The performance test results show that indole compounds used as blue light absorbers in examples 5-7 of the invention achieve the blue light prevention effect of comparative example 2 with less addition amount (0.1%), and the yellow index is lower, which is close to the level of casting common lenses under the test condition (comparative example 1), the aging resistance is improved, the service life is prolonged, and the product performance is obviously increased.
The blue light resistance of the blue light-proof substrate lens is the obstruction of a visible light 400-450nm waveband, and the waveband is high-energy short-wave blue light which is harmful to eyes. The listed cutoff wavelength T% means that the maximum wavelength with the transmittance less than 2% is about 410nm, and then is in a curve shape, part of blue light is gradually transmitted at 450nm, which mainly plays a role in completely blocking the blue light with the highest energy of the 400-410nm part, and the blue light with the wavelength of 410-450nm is partially transmitted. One of the main reasons for this is that if the blue light is totally blocked the lens turns yellow completely (as reflected by the yellow index), adding discomfort to the customer for normal use. In comprehensive consideration, it is considered that the lower the yellowness index is, the better the performance of the lens with the longer life is when the cutoff wavelength is controlled to be larger than 410nm, and examples 5 to 7 each have advantages, and the most preferable is example 6.
Example 5 compared to comparative example 1, example 5 increased the blue light absorber, and example 5 slightly worse in yellowness index by 3.8% than comparative example 1, less difference, with a cutoff wavelength greater than 410nm, had a blue light resistance effect, whereas comparative example 1 did not. The falling ball impact resistance is a conventional test and is qualified. The anti-aging performance of the lens in example 5 is that under the same test conditions, after the anti-blue light absorber is added, the stability of the lens after being irradiated by ultraviolet light is increased, while the stability of the lens in comparative example 1 without the blue light absorber is the worst, and the yellowing phenomenon is the most serious after being irradiated by light for a long time.
Example 6 compared with comparative example 2, example 6 used ultraviolet absorber UV326, the addition amount was 1%, the yellow index of example 6 compared with comparative example 2 was greatly reduced, the UV cut-off wavelength reached 414nm, the absorption effect of the lens on harmful blue light was better than that of comparative example 2, the aging resistance (or yellowing resistance) reached 2000h, and the test result was twice that of comparative example 2. In example 6, the blue light absorber is added by 0.1%, and in example 6, the ultraviolet absorber UV326 is added by 1%, and as can be seen from the cut-off wavelength data, the blue light prevention effect of example 6 is better than that of comparative example 2, which shows that the effect of the UV absorber 10 times can be achieved by using a small amount of blue light absorber, and the performance is more excellent.
Comparative example 3
The substrate lens prepared in the prior art comprises the following specific components in parts by weight as shown in table 7:
TABLE 7
| Composition (I) | Parts by weight | |
| Monofunctional reactive monomer | Methyl styrene | 50 portions of |
| Polyfunctional reactive monomer | Ethoxylated bisphenol A diacrylate | 40 portions of |
| Oligomer | Polyester acrylate | 10 portions of |
The amount of azobisisoheptonitrile added as an initiator was 0.1% of the total mass of the monofunctional reactive monomer, the polyfunctional reactive monomer, the oligomer and the initiator (in this example, 0.1 part by weight). The amount of the ultraviolet absorber UV326 added was 0.1% by mass of the total mass of the monofunctional reactive monomer, the polyfunctional reactive monomer, the oligomer and the initiator (in this example, 0.1 part by mass).
The preparation method is the same as example 5.
Performance data for comparative example 3: the yellow index is 8.63, the UV cut-off wavelength is 395nm, the falling ball impact performance is qualified, and the ageing resistance is 1000 h.
Compared with example 6, the UV cut-off wavelength of comparative example 3 is only 395nm in the ultraviolet region, and the UV cut-off wavelength of example 6 is 414nm, and it can be seen from the above data that the UV cut-off wavelength of comparative example 3 cannot achieve the effect of isolating most of short-wave blue light, i.e., has no effect of resisting blue light. Illustrating that comparative example 3 added the same amount of the ultraviolet absorber UV326 as that of inventive example 6, comparative example 3 did not have an effect of resisting blue light, while inventive example 6 had an effect of resisting blue light. The yellowness index of comparative example 3 was 8.63, the yellowness index of example 6 was 8.12, and the yellowness index of comparative example 3 was higher than that of example 6. The aging resistance of the comparative example 3 is 1000 hours, the aging resistance of the example 6 is 2000 hours, and the aging resistance of the example 6 is twice that of the comparative example 3, which shows that the blue light resistant effect can be achieved by adding a small amount (one tenth of that of the conventional blue light absorbent) of the blue light absorbent in the example 6 of the invention, and meanwhile, the yellow index and the aging resistance are excellent.
Although the present invention has been described with reference to a preferred embodiment, it should be understood that various changes, substitutions and alterations can be made herein without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (10)
1. An indole compound, characterized by the following structural formula:
wherein R is1Selected from hydrogen, C1～C8Straight chain alkyl group of (1), C1～C8An alkyl group having a branched chain,
R3Selected from hydrogen, methyl, ethyl, methoxy, ethoxy;
R2selected from hydrogen, C1～C8Straight chain alkyl group of (1), C1～C8An alkyl group containing a branch.
2. The indole compound of claim 1, wherein R is selected from the group consisting of1Selected from hydrogen, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl,
R3Selected from hydrogen, methyl, ethyl, methoxy, ethoxy; r2Selected from hydrogen,Methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl.
3. The indole compound of claim 2, wherein the structure of the indole compound is selected from one of the following structures:
4. use of an indole compound according to any one of claims 1 to 3 in the preparation of a blue-light absorber.
5. The blue-light-proof substrate lens is characterized by being prepared from the following components in parts by weight: 25-75 parts of monofunctional group reaction monomer, 25-75 parts of polyfunctional group reaction monomer and 0-10 parts of oligomer, and adding an initiator and a blue light absorbent, wherein the addition amount of the initiator accounts for 0.1-0.15% of the total mass of the monofunctional group reaction monomer, the polyfunctional group reaction monomer, the oligomer, the initiator and the blue light absorbent, and the addition amount of the blue light absorbent accounts for 0.01-0.15% of the total mass of the monofunctional group reaction monomer, the polyfunctional group reaction monomer, the oligomer, the initiator and the blue light absorbent;
the blue-light absorber is the indole compound according to any one of claims 1 to 3.
6. The blue-light resistant substrate lens according to claim 5, wherein the blue-light resistant substrate lens is prepared from the following components in parts by weight: 50-75 parts of monofunctional group reaction monomer, 25-45 parts of polyfunctional group reaction monomer and 5-10 parts of oligomer, and adding an initiator and a blue light absorbent, wherein the adding amount of the initiator accounts for 0.1% of the total mass of the monofunctional group reaction monomer, the polyfunctional group reaction monomer, the oligomer, the initiator and the blue light absorbent, and the adding amount of the blue light absorbent accounts for 0.1% of the total mass of the monofunctional group reaction monomer, the polyfunctional group reaction monomer, the oligomer, the initiator and the blue light absorbent.
7. The blue-light blocking substrate lens according to claim 5, wherein the monofunctional reactive monomer is selected from the group consisting of styrene, methacrylic acid, acrylic acid, methylstyrene, butyl acrylate, isooctyl acrylate, ethyl methacrylate, cyclohexyl acrylate, benzyl acrylate, ethoxylated nonylphenol acrylate, hydroxyethyl acrylate, o-phenylphenoxyethyl acrylate, tetrahydrofurfuryl acrylate.
8. The blue-light blocking substrate lens according to claim 5, wherein the polyfunctional reactive monomer is selected from the group consisting of dipropylene glycol diacrylate, tripropylene glycol diacrylate, polyethylene glycol diacrylate, ethoxylated bisphenol A diacrylate, polyethylene glycol dimethacrylate, propoxylated glycerol triacrylate, pentaerythritol tetraacrylate, ethoxylated pentaerythritol tetraacrylate.
9. The blue-blocking substrate lens of claim 5, wherein the oligomer is selected from the group consisting of aliphatic urethane acrylate oligomers, aromatic urethane acrylates, epoxy acrylates, bisphenol A epoxy acrylates, polyester acrylates;
the initiator is selected from diisopropyl peroxydicarbonate, dicyclohexyl peroxydicarbonate, benzoyl peroxide, dicumyl peroxide, tert-butyl peroxybenzoate, azobisisobutyronitrile and azobisisoheptonitrile.
10. The blue-light preventing substrate lens according to claim 5, wherein the method for preparing the blue-light preventing substrate lens comprises the steps of:
step one, uniformly mixing a monofunctional group reaction monomer, a polyfunctional group reaction monomer, an oligomer and a blue light absorbent, adding an initiator, vacuumizing for 10-60 min at room temperature, controlling the temperature to be 35-50 ℃, standing and vacuumizing for 10-60 min;
secondly, filtering the uniformly mixed mixture prepared in the first step, injecting the mixture into a mold for sealing, and carrying out programmed temperature rise to 95 ℃ from room temperature in a curing furnace for 20 hours to finish primary curing to obtain a lens;
temperature programmed curve: keeping the temperature for 0-5h at 34 ℃; uniformly rising the temperature to 50 ℃ within 5-12 h; ③ rising to 95 ℃ at a constant speed for 12-18 h; fourthly, keeping the temperature for 18 to 20 hours at 95 ℃;
and thirdly, performing die sinking, edge cutting and cleaning procedures on the lens obtained in the second step, and performing secondary curing molding at a constant temperature of 105-115 ℃ for 1-2 hours to obtain the blue light-proof substrate lens.
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| CN115181207A (en) * | 2022-04-22 | 2022-10-14 | 江苏康耐特光学有限公司 | Blue-light-proof resin lens with refractive index of 1.50 and preparation method thereof |
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| CN114031547B (en) | 2023-05-30 |
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