CN108467390B - Thiophene dimethylketoxime acetate containing biscarbazole as photoinitiator, preparation method and application thereof - Google Patents
Thiophene dimethylketoxime acetate containing biscarbazole as photoinitiator, preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to a preparation method of thiophene dimethyloxime acetate containing biscarbazole as a photoinitiator. Reacting carbazole and 1-bromobutane in a potassium hydroxide and DMSO system to obtain an intermediate I; carrying out nitration reaction on the intermediate I and nitric acid to obtain an intermediate II; under the catalytic action of aluminum trichloride, carrying out Friedel-Crafts reaction on the intermediate II and 2, 5-di (chloroformyl) thiophene to obtain an intermediate III; and reacting the intermediate III with hydroxylamine hydrochloride to obtain an intermediate IV under the condition of a mixed solvent of methanol and water, and finally reacting the intermediate IV with acetic anhydride to obtain the target compound photoinitiator, namely the thiophene dimethyloxime acetate containing the dicarbazole. The preparation method has the advantages of simple operation, advanced process, recyclable solvent and easy industrial production.
Description
Technical Field
The invention belongs to the field of photoinitiators, and particularly relates to a preparation method of a dicarbazole-containing thiophene dimethyloxime acetate photoinitiator.
Technical Field
Carbazole has a good rigid conjugated plane, has a strong intramolecular electron transfer performance and an excellent photoelectric property, and provides favorable conditions for the derivative of carbazole to be used as a good two-photon photoinitiator. Carbazole oxime ester is a novel carbazole two-photon photoinitiator, the electron-donating capability of a conjugated system can be enhanced by introducing alkyl on the nitrogen atom of carbazole, conjugated aromatic acyl and oxime ester electron-withdrawing groups are connected on the carbazole ring to increase the conjugated chain, so that the electron transfer degree in the molecule is increased, and the two-photon fluorescence property is improved. Since carbazolyl ketoxime acetate compounds have many of the above advantages and are used as initiators for acrylate systems, printing inks, photocurable coatings, etching resists, plating resists, hologram recording materials, pressure-sensitive adhesives, laminating resins, it is necessary to develop novel dicarbazole oxime ester photoinitiators.
Disclosure of Invention
The invention aims to provide a preparation method of thiophene dimethylglyoxime acetate containing dicarbazole, which has the advantages of simple process, high yield, low cost, small pollution and good product quality and is suitable for industrial production. In order to solve the technical problem, the invention aims to realize the following steps: a bis-carbazole containing thiophene dimethyloxime acetate photoinitiator, which has the following chemical structural formula:
the photoinitiator contains thiophene dimethylketoxime acetate of biscarbazole.
The invention adopts the following technical scheme:
a: adding an organic solvent, carbazole and potassium hydroxide into a reactor with a stirrer, slowly dropwise adding 1-bromobutane into the reactor, controlling the temperature of the reaction liquid to be 80-120 ℃, and reacting for 2.0-4.0 h. After the reaction is completed, ethyl acetate-water (V) is addedEthyl acetate:VWater (W)1) mixing the solution, separating a water layer, and recovering an organic solvent ethyl acetate by reduced pressure distillation to obtain an intermediate I;
b: adding the organic solvent and the intermediate I into a reactor provided with a stirrer, controlling the temperature to be minus 10-10 ℃, slowly dropwise adding nitric acid into the reactor, controlling the temperature of the reaction liquid to be minus 10-10 ℃, and reacting for 2.0-6.0 h. After the reaction is finished, adding water, separating out a water layer, and drying to obtain an organic solvent solution containing the intermediate II, wherein the organic solvent solution is directly used for preparing the intermediate III in the Friedel-Crafts reaction in the next step;
c: adding aluminum trichloride into an organic solution containing an intermediate II, controlling the temperature in a reaction kettle to be 0-30 ℃, stirring for 1.0-2.0h, slowly dropwise adding a dichloroethane solution of 2, 5-di (chloroformyl) thiophene, controlling the temperature in the reaction kettle to be 0-30 ℃ after dropwise adding, reacting for 6.0-8.0h, adding a hydrochloric acid solution with mass fraction into the reaction kettle after the reaction is finished, stirring for 1.0h, standing, layering, washing an organic phase with water and sodium bicarbonate for three times, evaporating an organic solvent under reduced pressure, and recrystallizing to obtain an intermediate III, wherein the reaction equation is as follows:
d: adding an organic solution, adding an intermediate III and hydroxylamine hydrochloride into a reactor, heating to 60-100 ℃, dropwise adding a sodium acetate solution, controlling the temperature in the reaction kettle to be 60-100 ℃ after dropwise adding, reacting for 7-10h, adding water into the reactor after the reaction is finished, stirring for 1h, standing, layering, distilling out an organic solvent under reduced pressure, and recrystallizing to obtain an intermediate IV, wherein the reaction equation is as follows:
e: adding dichloroethane and the intermediate IV into a reactor, controlling the temperature to be 0-20 ℃, dropwise adding acetic anhydride, controlling the temperature in the reaction kettle to be 0-20 ℃ after dropwise adding, reacting for 6.0-10h, adding a sodium hydroxide aqueous solution into the reactor after the reaction is finished, stirring for 2h, standing, layering, decompressing and distilling out an organic solvent, and recrystallizing to obtain a target compound, wherein the reaction equation is as follows:
thiophene dimethylketoxime acetate containing biscarbazole.
In the step A, the mass ratio of carbazole, 1-bromobutane and potassium hydroxide is 1: 1-1.3: 1.2-2.0, wherein the organic solvent is any one of dimethyl sulfoxide, N-dimethylformamide or acetone, and dimethyl sulfoxide is preferred; the weight of the organic solvent is 7-12 times of that of the carbazole; the preferred reaction temperature is 90-100 ℃.
In the step B, the mass ratio of the intermediate I to the nitric acid is 1: 1-1.6, wherein the organic solvent is any one of nitrobenzene, dichloroethane or dichloromethane, preferably dichloroethane; the weight of the organic solvent is 8-12 times of that of the intermediate I; the preferred reaction temperature is-5-0 ℃.
In the step C, the mass ratio of the 2, 5-di (chloroformyl) thiophene, the aluminum trichloride and the intermediate II is 1: 2.3-2.5: 2.2-3.0, the organic solvent is any one of nitrobenzene, dichloroethane or dichloromethane, preferably dichloroethane, and the weight of the organic solvent is 7-12 times that of the intermediate II; the preferred reaction temperature is 10-15 ℃.
In the step D, the mass ratio of the intermediate III, the hydroxylamine hydrochloride and the sodium acetate is 1:2.0-2.2:2-2.5, the organic solvent is ethanol-water, and V isEthanol:VWater (W)1:1, methanol-water, VMethanol:VWater (W)1:1 or DMF-water, VDMF:VWater (W)(1: 1) the mixed solution is preferably methanol-water, VMethanol:VWater (W)1:1 mixed solution; the weight of the organic solvent is 10-12 times of that of the intermediate III; the preferred reaction temperature is 80-90 ℃.
In the step E, the mass ratio of the intermediate IV to acetic anhydride is 1:2.0-2.5, the organic solvent is any one of dichloroethane and dichloromethane, preferably dichloromethane; the weight of the organic solvent is 8-10 times of that of the intermediate IV; the preferred reaction temperature is 5-10 ℃.
In the step B, the mass fraction of the nitric acid is 55-70%; in the step C, the mass fraction of the hydrochloric acid is 10-20%; in the step D, the mass fraction of sodium nitrate is 5-15%; in the step D, the mass fraction of the sodium hydroxide is 3-10%.
In the step B, the mass fraction of the nitric acid is 68 percent; in the step C, the mass fraction of the hydrochloric acid is 15 percent; in the step D, the mass fraction of sodium nitrate is 10%; in the step D, the mass fraction of the sodium hydroxide is 5%.
The technical scheme of the invention is to apply the prepared photoinitiator thiophene dimethyloxime acetate containing biscarbazole in acrylic epoxy resin.
The invention has the following beneficial effects:
1. a complete process for the preparation of biscarbazole-containing thiophenedicarboxime acetate is provided.
2. The prepared thiophene dimethylketoxime acetate containing biscarbazole overcomes the defects of low sensitivity, poor solubility, large influence of air on photocuring, poor storage stability and the like of the conventional photoinitiator generally, and the initiator can be applied to the manufacturing requirements of RGB (Red Green blue) key components of a new-generation large-screen LCD (liquid crystal display).
3. The novel dicarbazole-containing thiophene dimethylketoxime acetate is prepared by constructing photosensitive groups such as dicarbazole-containing biscarbazolyl, thiophene formyl and oxime acetate groups on the same molecule, and the photoinitiator has the advantages of high photoinitiation speed, excellent deep curing and wide spectrum absorption range.
4. The photoinitiator has good photocuring effect on acrylic epoxy resin.
Detailed Description
The invention is further illustrated by the following examples, but the scope of the invention as claimed is not limited to the examples.
Example 1:
a preparation method of thiophene dimethyloxime acetate containing dicarbazole comprises the following steps:
100mL of dimethyl sulfoxide (DMSO), 16.72g (0.10mol) of carbazole and 8.42g (0.15mol) of potassium hydroxide are added into a reactor provided with a stirrer, 17.81g (0.13mol) of 1-bromobutane is slowly dripped into the reactor, the temperature of the reaction solution is controlled to be 90-100 ℃, and the reaction lasts for 3.0-3.5 h. After the reaction is completed, ethyl acetate-water (V) is addedEthyl acetate:VWater (W)2:1) 150mL of the mixed solution, separating the aqueous layer, and recovering the organic solvent by distillation under reduced pressure to obtainObtaining an intermediate I;
preparation of intermediate II
160mL of dichloroethane and 22.34g (0.10mol) of the intermediate I are added into a reactor provided with a stirrer, the temperature is controlled to be between-5 and 0 ℃, 11.12g (0.12mol) of nitric acid with the mass fraction of 68 percent is slowly dripped into the reactor, the temperature of the reaction liquid is controlled to be between-5 and 0 ℃, and the reaction is carried out for 4.0 to 5 hours. After the reaction is finished, adding water, separating out a water layer, and drying to obtain a dichloroethane solution containing an intermediate II, wherein the dichloroethane solution is directly used for preparing an intermediate III;
preparation of intermediate III
Adding 180mL of dichloroethane and 26.84g (0.20mol) of the intermediate II into a reactor provided with a stirrer, adding 32.01g (0.24mol) of aluminum trichloride, controlling the temperature in the reactor to be 10-15 ℃, stirring for 1.0-2.0h, slowly dropwise adding 100mL of 2, 5-bis (chloroformyl) thiophene 20.91g (0.10mol) dichloroethane mixed solution, controlling the temperature in the reactor to be 10-15 ℃ after dropwise adding, reacting for 7-8h, adding a hydrochloric acid solution with the mass fraction of 15% into the reactor after the reaction is finished, stirring for 1h, standing, layering, washing an organic phase with water and sodium bicarbonate for three times, decompressing and distilling out an organic solvent, and crystallizing to obtain an intermediate III;
preparation of intermediate IV
Methanol-water (V) is added to the reactorMethanol:VWater (W)1:1) adding 180mL of mixed solution, adding 67.28g (0.10mol) of intermediate III and 15.31g (0.22mol) of hydroxylamine hydrochloride, heating to 65-70 ℃, dropwise adding 353.62g (0.26mol) of 10% sodium acetate solution, controlling the temperature in a reaction kettle to react at 80-90 ℃ for 8-9h after dropwise adding, adding water into the reactor after the reaction is finished, stirring for 1h, standing, layering, evaporating an organic solvent under reduced pressure, and recrystallizing to obtain intermediate IV;
preparation of target compound thiophene dimethyloxime acetate containing biscarbazole
200mL of dichloroethane and 70.28g (0.10mol) of the intermediate IV were added to the reactor, and 20.42g (0.20mol) of acetic anhydride was added dropwise while controlling the temperature at 5 to 10 ℃. After the dropwise addition, controlling the temperature in the reaction kettle to react at 5-10 ℃ for 7-8h, after the reaction is finished, adding 260mL of sodium hydroxide aqueous solution with the mass fraction of 5% into the reactor, stirring for 1h, standing, layering, evaporating the organic solvent under reduced pressure, and recrystallizing to obtain the target compound with the yield of 71.5%.
1H NMR(DMSO-d6,400MHz)δ:9.21-9.11(m,2H,Ar-H),8.67-8.60m,4H,Ar-H),7.91-7.53(m,5H,Ar-H),7.16-7.11(m,3H,Ar-H),4.58(d,4H,NCH2),2.22(s,6H,CH3),1.74-1.69(m,4H,CH2),1.28-1.25(m,4H,CH2),0.84(t,6H,CH3).
Example 2:
the amount of acetic anhydride was increased to 22.46g (0.22mol) and the yield of the target biscarbazole-containing thiophenedicarboxymethyloxime acetate was 75.3% as in example one.
Example 3:
the amount of acetic anhydride was increased to 24.51g (0.24mol), and the yield of the target compound biscarbazole-containing thiophenedicarboxymethyloxime acetate was 80.2% as in the other example one.
Example 4:
the amount of acetic anhydride was increased to 26.55g (0.26mol), and the yield of the target compound, biscarbazole-containing thiophenedicarboxymethyloxime acetate, was 87.5% as in the other example one.
Example 5:
the amount of acetic anhydride was increased to 28.59g (0.28mol), otherwise in the same example-yield 88.2% of biscarbazole-containing thiophenedicarboxime acetate.
Example 6:
the amount of acetic anhydride was increased to 30.63g (0.3mol), otherwise in the same way as in example one, the yield of the target compound biscarbazole-containing thiophenedicarboxymethyloxime acetate was 81.7%.
Example 7:
the photoinitiator biscarbazole-containing thiophene dimethyloxime acetate and commercially available TPO (2,4, 6-trimethylbenzoyldiphenylphosphine oxide) prepared in the examples were added to an acrylic epoxy resin sample system (formulation: 30% of bisphenol A epoxy acrylate, 8% of aminoacrylate, 30% of propoxylated glycerol triacrylate, 24% of hexanediol diacrylate, 0.5% of polysiloxane acrylate and 3.5% of ethoxypentaerythritol tetraacrylate) at a ratio of 4% by mass, respectively, and uniformly coated on a washed and dried copper-clad plate, and irradiated with a 1kw high-pressure mercury lamp to cure the liquid film, and the measurement results are shown in Table 1 below.
TABLE 1 photocuring Effect of photoinitiators of the invention on epoxy acrylates
Claims (1)
1. The application of the thiophene dimethyloxime acetate containing biscarbazole as the photoinitiator in the acrylic epoxy resin is characterized in that the thiophene dimethyloxime acetate containing biscarbazole as the photoinitiator is added into an acrylic epoxy resin sample system according to the proportion of 4% by mass, and the formula of the acrylic epoxy resin sample system is as follows: 30% of bisphenol A epoxy acrylate; 8% of amino acrylate; propoxylated glycerol triacrylate 30%; 24% of hexanediol diacrylate; 0.5 percent of polysiloxane acrylate; 3.5 percent of ethoxy pentaerythritol tetraacrylate is uniformly coated on a washed and dried copper clad plate, and a 1kw high-pressure mercury lamp is used for irradiation, so that a liquid film is polymerized and cured, the photocuring speed is 85 m/min, and the chemical structural formula of the dicarbazole-containing thiophene dimethyloxime acetate of the photoinitiator is as follows:
the preparation method of the thiophene dimethyloxime acetate containing biscarbazole comprises the following steps:
adding 100mL of dimethyl sulfoxide, 16.72g of carbazole and 8.42g of potassium hydroxide into a reactor with a stirrer, slowly dropwise adding 17.81g of 1-bromobutane into the reactor, controlling the temperature of the reaction solution to be 90-100 ℃, reacting for 3.0-3.5h, and adding ethyl acetate-water V after the reaction is finishedEthyl acetate:VWater (W)150mL of the mixed solution with the ratio of 2:1, separating out a water layer, and recovering the organic solvent by reduced pressure distillation to obtain an intermediate I;
preparation of intermediate II
Adding 160mL of dichloroethane and 22.34g of the intermediate I into a reactor provided with a stirrer, controlling the temperature to be-5-0 ℃, slowly dropwise adding 11.12g of nitric acid with the mass fraction of 68% into the reactor, controlling the temperature of the reaction liquid to be-5-0 ℃, reacting for 4.0-5h, adding water after the reaction is finished, separating out a water layer, and drying to obtain dichloroethane solution containing the intermediate II, wherein the dichloroethane solution is directly used for preparing the intermediate III;
preparation of intermediate III
Adding 180mL of dichloroethane and 26.84g of intermediate II into a reactor provided with a stirrer, adding 32.01g of aluminum trichloride, controlling the temperature in the reaction kettle to be 10-15 ℃, stirring for 1.0-2.0h, slowly dropwise adding 100mL of 2, 5-di (chloroformyl) thiophene 20.91g of dichloroethane mixed solution, controlling the temperature in the reaction kettle to react for 7-8h at 10-15 ℃ after dropwise adding, adding 15 mass percent hydrochloric acid solution into the reactor after the reaction is finished, stirring for 1h, standing, layering, washing an organic phase with water and sodium bicarbonate for three times, distilling out a reduced-pressure organic solvent, and crystallizing to obtain an intermediate III;
preparation of intermediate IV
Methanol-water V is added into a reactorMethanol:VWater (W)Adding 180mL of a 1:1 mixed solution, adding 67.28g of an intermediate III and 15.31g of hydroxylamine hydrochloride, heating to 65-70 ℃, dropwise adding 353.62g of a 10% sodium acetate solution, controlling the temperature in a reaction kettle to react at 80-90 ℃ for 8-9h after dropwise adding, adding water into the reactor after the reaction is finished, stirring for 1h, standing, layering, evaporating an organic solvent under reduced pressure, and recrystallizing to obtain an intermediate IV;
preparation of target compound thiophene dimethyloxime acetate containing biscarbazole
Adding 200mL of dichloroethane, 70.28g of the intermediate IV into the reactor, controlling the temperature to be 5-10 ℃, and dropwise adding 28.59g of acetic anhydride; and after the dropwise addition is finished, controlling the temperature in the reaction kettle to react for 7-8h at 5-10 ℃, after the reaction is finished, adding 260mL of sodium hydroxide aqueous solution with the mass fraction of 5% into the reactor, stirring for 1h, standing, layering, evaporating the organic solvent under reduced pressure, and recrystallizing to obtain the target compound.
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