CN119431168A - A photosensitizer and its preparation method and application - Google Patents
A photosensitizer and its preparation method and application Download PDFInfo
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Abstract
本发明涉及有机化学品技术领域，具体涉及一种光敏剂及其制备方法和应用。所述光敏剂的结构如式（I）所示，本发明的光敏剂无刺激性气味，固化性和附着力好，生物毒性更低。
The present invention relates to the technical field of organic chemicals, and in particular to a photosensitizer and a preparation method and application thereof. The structure of the photosensitizer is shown in formula (I). The photosensitizer of the present invention has no irritating odor, good curing property and adhesion, and lower biological toxicity.
Description
Technical Field
The invention relates to the technical field of organic chemicals, in particular to a photosensitizer and a preparation method and application thereof.
Background
Photosensitizers, also known as photoinitiators, are broadly divided into free radical type and ionic type, the former being used to initiate polymerization of vinyl functional groups, and are subdivided into two broad categories, direct cleavage type and hydrogen abstraction type, with α -substituted acetophenones and acylphosphine oxides being representative direct cleavage type photoinitiators, benzophenone and thioxanthones being representative hydrogen abstraction type photoinitiators. Chinese patent CN1281577C discloses a photosensitive quaternary ammonium salt, which can generate free radical and tertiary amine after photolysis, and is a quaternary ammonium salt of an aryl ketone based on dialkylamino. These initiators all have the disadvantage of being relatively toxic.
In recent years, a large number of photoinitiators have been disabled due to toxic or reproductive toxicity, and thus the design and development of new photosensitizers has been of increasing interest.
The photosensitizer commonly used in the current paint and ink is benzophenone, which has the main defects of strong and unpleasant pungent smell of benzophenone left on the product after use, bitter taste of residual odor for consumers, higher biological toxicity and poor solidification and adhesion.
Therefore, it is necessary to develop a photosensitizer capable of solving the above technical problems, and a preparation method and application thereof.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a photosensitizer with no pungent smell, good solidification and adhesive force and lower biotoxicity, and a preparation method and application thereof.
The invention is realized by the following technical scheme:
the invention provides a photosensitizer, the chemical name of which is 2,4, 6-trimethyl-4' -diethylaminobenzophenone, and the structure of the photosensitizer is shown as a formula (I):
(I)。
The second aspect of the invention provides a preparation method of the photosensitizer, comprising the following steps:
S1, adding anhydrous aluminum chloride, an organic solvent A and 2,4, 6-trimethyl benzoyl chloride into a reaction bottle, adding N, N-diethyl aniline under stirring, heating and refluxing to react, adding a reaction solution into a hydrochloric acid aqueous solution, extracting by adopting the organic solvent A, washing an organic phase A obtained by extraction by adopting a saturated sodium bicarbonate solution, water and saturated saline in sequence, and drying to obtain an organic phase B;
S2, filtering the organic phase B, removing the organic solvent A to obtain brown yellow oily matter, adding the nonpolar organic solvent, stirring to obtain a solid C, and washing or recrystallizing with a mixed solvent to obtain the solid C;
The reaction formula is as follows:
。
in some embodiments of the invention, in step S1, the organic solvent a is selected from one or more of dichloromethane, chloroform, 1, 2-dichloroethane, carbon tetrachloride, 1-dichloroethane, preferably dichloromethane.
In some embodiments of the invention, in step S1, the mass ratio of the volume of the organic solvent A to the 2,4, 6-trimethylbenzoyl chloride is 3-5mL to 1g.
In some embodiments of the invention, in step S1, the ratio of the amounts of the anhydrous aluminum chloride, 2,4, 6-trimethylbenzoyl chloride and N, N-diethylaniline is between 1.01 and 1.5:1:1.01 and 2.5.
In some embodiments of the present invention, in step S1, the reflux reaction time is 12h-24, the mass concentration of the aqueous hydrochloric acid solution is 10-15%, and the temperature is-5 ℃.
In some embodiments of the invention, in step S1, the organic phase a is obtained by three times of extraction with the organic solvent a and combining the organic phases.
In some embodiments of the invention, in step S1, the saturated sodium bicarbonate solution is washed to weak alkalinity.
In some embodiments of the invention, in step S1, anhydrous sodium sulfate is used for drying.
In some embodiments of the present invention, in step S2, the organic solvent a is removed by spin evaporation under reduced pressure.
In some embodiments of the present invention, in step S2, the nonpolar organic solvent is selected from one or both of petroleum ether and cyclohexane.
In some embodiments of the present invention, in step S2, the mixed solvent is composed of a solvent 1 and a solvent 2, wherein the solvent 1 is selected from one of petroleum ether and cyclohexane, the solvent 2 is selected from one of ethyl acetate, dichloromethane and methanol, and the mixed solvent is specifically selected from one of petroleum ether/ethyl acetate, cyclohexane/ethyl acetate, petroleum ether/dichloromethane, cyclohexane/dichloromethane, petroleum ether/methanol and cyclohexane/methanol. The volume ratio of the solvent 1 to the solvent 2 is 1-50:1.
The third aspect of the invention provides a preparation method of the photosensitizer, comprising the following steps:
(1) Adding anhydrous aluminum chloride and an organic solvent D into a reaction bottle, adding 4-chlorobenzoyl chloride at a temperature of-5 ℃, stirring and reacting for 0.5-1h, adding 1,3, 5-trimethylbenzene, continuously reacting for 1-3h at a temperature of 10-25 ℃, adding the reaction solution into a hydrochloric acid aqueous solution, extracting by adopting the organic solvent D, washing an organic phase D obtained by extraction by adopting a saturated sodium bicarbonate solution, water and saturated saline in sequence, and drying to obtain an organic phase E;
(2) Filtering the organic phase E, removing the organic solvent D to obtain a solid F, adding a polar organic solvent, diethylamine and an inorganic basic compound into the solid F, carrying out reaction at a certain temperature, cooling to room temperature after the reaction is finished, adding water to separate out solid, and washing with petroleum ether to obtain the catalyst;
The reaction formula is as follows:
。
in some embodiments of the invention, the ratio of the amounts of anhydrous aluminum chloride, 4-chlorobenzoyl chloride and 1,3, 5-trimethylbenzene in step (1) is 1-2:1:1-3.
In some embodiments of the present invention, the organic solvent D in the step (1) is selected from one or more of chloroform, dichloromethane and 1, 2-dichloroethane, and the mass concentration of the aqueous hydrochloric acid solution is 10-15%, and the temperature is-5 ℃.
In some embodiments of the present invention, the polar organic solvent in step (2) is selected from one or two of N, N-dimethylformamide, N-dimethylacetamide and N-methylpyrrolidone, the inorganic basic compound is selected from one or two of potassium carbonate, sodium carbonate, potassium hydroxide and sodium hydroxide, and the temperature is 100-200 ℃ and the reaction time is 12-24 hours.
In some embodiments of the invention, the amount of 4-chlorobenzoyl chloride, diethylamine, inorganic basic compound material is in the ratio of 1:1 to 3:1 to 2.
In some embodiments of the invention, the ratio of 4-chlorobenzoyl chloride to polar organic solvent is 1mol:50-100mL.
In a fourth aspect, the invention provides the use of a photosensitizer in the preparation of an ink, primarily in the field of inks.
The beneficial effects of the invention are as follows:
Compared with the photosensitizer benzophenone in the traditional printing ink, the photosensitizer 2,4, 6-trimethyl-4' -diethylaminobenzophenone has lower toxicity, no pungent smell, more excellent ultraviolet absorbability, curability and adhesive force, lower biotoxicity compared with tetramethyl ketone/tetraethyl ketone, and equivalent ultraviolet absorbability, curability and adhesive force.
Drawings
FIG. 1 is a nuclear magnetic resonance spectrum of the product prepared in example 1.
FIG. 2 is a nuclear magnetic resonance spectrum of the product prepared in example 4.
Detailed Description
The invention will be further described with reference to specific embodiments, and advantages and features of the invention will become apparent from the description. These examples are merely exemplary and do not limit the scope of the invention in any way. It will be understood by those skilled in the art that various changes and substitutions of details and forms of the technical solution of the present invention may be made without departing from the spirit and scope of the present invention, but these changes and substitutions fall within the scope of the present invention.
"Eq" in each example of the present invention represents the equivalent amount of a substance.
Example 1
The preparation of 2,4, 6-trimethyl-4' -diethylaminobenzophenone is carried out as follows:
。
To the reaction flask, 1.01eq of anhydrous aluminum chloride was added, 50mL of methylene chloride and 1.0eq of 2,4, 6-trimethylbenzoyl chloride were added, and 1.01eq of N, N-diethylaniline was added under stirring, followed by heating and refluxing for 12 hours. After the reaction, the reaction solution was slowly added dropwise to a 15wt% aqueous hydrochloric acid solution at-5 ℃ for three times of extraction with methylene chloride, the organic phases were combined, washed with saturated NaHCO 3 solution to be weakly alkaline, washed with purified water, washed with saturated brine and dried over anhydrous sodium sulfate.
The organic phase obtained after drying was filtered and the solvent was removed by rotary evaporation under reduced pressure to give a tan oil in 87% yield. Petroleum ether was added to the brown yellow oil and stirred to give a pale yellow powdered solid in 83% crude yield. And washed with petroleum ether, ethyl acetate=30:1. The product reaching the standard is yellowish, the yield is 70 percent, and the purity is 99.03 percent.
The nuclear magnetic hydrogen spectrogram is shown in figure 1.
Mass spectrometry data:
c 20H25 NO: LCMS-IT-TOF high-resolution mass spectrum [ M+H ] +:296.1997, theory 296.2009.
Example 2
The preparation of 2,4, 6-trimethyl-4' -diethylaminobenzophenone is carried out as follows:
。
To the reaction flask, 1.2eq of anhydrous aluminum chloride, 50mL of 1, 2-dichloroethane and 1.0eq of 2,4, 6-trimethylbenzoyl chloride were added, and 1.5eq of N, N-diethylaniline was added under stirring, followed by thermal reflux reaction for 24 hours. After the reaction, the reaction solution was slowly added dropwise to a 10wt% aqueous hydrochloric acid solution at 0℃and extracted three times with 1, 2-dichloroethane, the organic phases were combined, washed with saturated NaHCO 3 solution to weakly alkaline, washed with purified water, washed with saturated brine and dried over anhydrous sodium sulfate.
The organic phase obtained after drying was filtered and the solvent was removed by rotary evaporation under reduced pressure to give a tan oil in 89% yield. Cyclohexane was added to the tan oil and stirred to give a pale yellow powdered solid in 85% crude yield. Washed with cyclohexane ethyl acetate=45:1. The product reaching the standard is yellowish, and the yield is 73 percent.
Example 3
The preparation of 2,4, 6-trimethyl-4' -diethylaminobenzophenone is carried out as follows:
。
To the reaction flask, 1.5eq of anhydrous aluminum chloride, 50mL of chloroform and 1.0eq of 2,4, 6-trimethylbenzoyl chloride were added, and 2.5eq of N, N-diethylaniline was added under stirring, followed by heating and refluxing for 12 hours. After the reaction, the reaction solution was slowly added dropwise to a 5 ℃ aqueous solution of 15wt% hydrochloric acid, chloroform extracted three times, the organic phases were combined, washed with saturated NaHCO 3 solution to be weakly alkaline, purified water, saturated brine and dried over anhydrous sodium sulfate.
The organic phase obtained after drying was filtered and the solvent was removed by rotary evaporation under reduced pressure to give a tan oil with a yield of 84%. Petroleum ether was added to the brown yellow oil and stirred to give a pale yellow powdered solid with a crude yield of 82%. And washed with petroleum ether, dichloromethane=20:1. The product reaching the standard is yellowish, and the yield is 71%.
Example 4
The preparation of 2,4, 6-trimethyl-4' -diethylaminobenzophenone is carried out as follows:
。
1.0eq of anhydrous aluminum chloride and 50mL of chloroform are added into a reaction bottle, 1.0eq of 4-chlorobenzoyl chloride is added at minus 5 ℃ and stirred for reaction for 0.5h, then 1.0eq of 1,3, 5-trimethylbenzene is added, the temperature is increased to 10 ℃ and the reaction is continued for 1h, after the reaction is finished, the reaction solution is slowly dripped into 10wt% hydrochloric acid aqueous solution at minus 5 ℃ and extracted for three times by chloroform, the organic phases are combined, saturated NaHCO 3 solution is washed to be alkalescent, purified water is washed, saturated saline water is washed, and anhydrous sodium sulfate is dried.
The organic phase obtained after drying was filtered and the solvent was removed by rotary evaporation under reduced pressure to give a yellow powdery solid in 90% yield. To the solid was added 50mL of N, N-dimethylformamide, 1.0eq of diethylamine and 1.0eq of K 2CO3, and the mixture was heated to 100℃and reacted for 12h. Cooling to room temperature, adding 200mL of water into the mixture to precipitate solid, filtering to obtain pale yellow powdery solid, and washing with 200mL of petroleum ether to obtain a yellowish product with a yield of 75%. The nuclear magnetic hydrogen spectrogram is shown in figure 2.
Example 5
The preparation of 2,4, 6-trimethyl-4' -diethylaminobenzophenone is carried out as follows:
。
2.0eq of anhydrous aluminum chloride, 100mL of dichloromethane and 5 ℃ of 4-chlorobenzoyl chloride are added into a reaction bottle, stirring is carried out for 1h, then 3.0eq of 1,3, 5-trimethylbenzene is added, the temperature is increased to 25 ℃, the reaction is continued for 3h, the reaction solution is slowly dripped into 15wt% hydrochloric acid aqueous solution at 5 ℃ after the reaction is finished, the dichloromethane is extracted for three times, the organic phases are combined, saturated NaHCO 3 solution is washed to be alkalescent, purified water is washed, saturated saline solution is washed, and anhydrous sodium sulfate is dried.
The organic phase obtained after drying was filtered and the solvent was removed by rotary evaporation under reduced pressure to give a yellow powdery solid with a yield of 92%. To the solid was added 100mL of N-methylpyrrolidone, 3.0eq of diethylamine and 2.0eq of KOH, and heated to 200℃for 24h. Cooling to room temperature, adding 200mL of water into the mixture to precipitate solid, filtering to obtain pale yellow powdery solid, and washing with 200mL of petroleum ether to obtain a yellowish product with a yield of 78%.
Comparative example 1
Photoinitiation performance comparison experiments of 2,4, 6-trimethyl-4' -diethylaminobenzophenone photosensitizer and benzophenone of example 1.
Prepared by mass percentage: UV ink prepolymer (a mixture of glycidyl acrylate and bis (trimethylolpropane) tetraacrylate in a ratio of 99:1) 70%, TPO-L (2,4,6-trimethylbenzoyl phenyl phosphonic acid ethyl ester) 3%, DETX (2,4-dimethylthioanthraquinone) 3%, paraffin powder 4%, kaolin 2.5%, carbon black 15%, and 2,4,6-trimethyl-4'- diethylaminobenzophenone 2.5%, finely dispersed three times through a three roll machine to obtain UV curable ink sample A with a fineness of less than or equal to 12.5μm.
And preparing a comparison sample according to the method, wherein 2,4, 6-trimethyl-4' -diethylaminobenzophenone is changed into the traditional photoinitiator benzophenone with equal mass, and the proportion of other raw materials is unchanged, so as to prepare the ultraviolet light photo-curing ink sample B.
Sample A and sample B were subjected to performance test comparison, referring to "preparation method of test sample for volatile organic Compound of printing Material for paper print" by CY/T127-2015, sample A or sample B was spread on 100g/m 2 offset paper to obtain print (ink thickness 30 μm), and cured by irradiation of LED-UV lamp with power density of 10W/cm 2 to obtain print to be tested containing ink sample for migration test.
Referring to general rules of food contact materials and product migration tests of national food safety standards of GB 31604.1-2023, the printed matter to be tested containing the ink sample is soaked in 20% (volume fraction) alcohol solution for 1-12 days, the specific migration is tested, compared with the result of a sample B (using traditional photoinitiator benzophenone), the migration of a sample A containing the photosensitizer 2,4, 6-trimethyl-4' -diethylaminobenzophenone of the invention is lower, and the migration test result is shown in Table 1.
TABLE 1 results of alcohol migration test (migration mg/m 2)
From the mobility data in Table 1, it is clear that sample A has lower mobility, indicating that it has better curing effect, stronger adhesion, lower dissolution in alcohol, and better alcohol resistance.
Comparative example 2
Cytotoxicity comparative experiment of the novel photosensitizer of 2,4, 6-trimethyl-4' -diethylaminobenzophenone (sample D) and tetraethyl mikanone (sample C) of example 1.
Hek293 line cells and Hek293T line cells were cultured in two 96-well plates, 10% fbs-DMEM was used as a medium, then samples C and D were added with different concentration gradients (0. Mu.M, 1. Mu.M, 5. Mu.M, 25. Mu.M, 125. Mu.M, 625. Mu.M, 3125. Mu.M), after waiting 24 hours, cell viability at different concentrations was measured with CCK8 kit, and IC 50 values were calculated.
Sample D and sample C were subjected to a biotoxicity comparison test in which sample D containing the photosensitizer 2,4, 6-trimethyl-4' -diethylaminobenzophenone of the present invention was less toxic than sample C (using the photoinitiator tetraethyl Mi ketone), and the results of the particular tests are shown in Table 2.
TABLE 2 comparative cytotoxicity experiments
The foregoing detailed description is directed to one of the possible embodiments of the present invention, which is not intended to limit the scope of the invention, but is to be accorded the full scope of all such equivalents and modifications so as not to depart from the scope of the invention.
Claims (10)
1. A photosensitizer is characterized in that the structure is shown as a formula (I):
(I)。
2. the method for preparing a photosensitizer according to claim 1, comprising the steps of:
S1, adding anhydrous aluminum chloride, an organic solvent A and 2,4, 6-trimethyl benzoyl chloride into a reaction bottle, adding N, N-diethyl aniline under stirring, heating and refluxing to react, adding a reaction solution into a hydrochloric acid aqueous solution, extracting by adopting the organic solvent A, washing an organic phase A obtained by extraction by adopting a saturated sodium bicarbonate solution, water and saturated saline in sequence, and drying to obtain an organic phase B;
S2, filtering the organic phase B, removing the organic solvent A to obtain brown yellow oily matter, adding the nonpolar organic solvent, stirring to obtain a solid C, and washing or recrystallizing with a mixed solvent to obtain the solid C;
The reaction formula is as follows:
。
3. The preparation method according to claim 2, wherein in the step S1, the reflux reaction time is 12-24 hours, the mass concentration of the aqueous hydrochloric acid solution is 10-15%, the temperature is-5 ℃, the organic solvent A is one or more selected from dichloromethane, chloroform, 1, 2-dichloroethane, carbon tetrachloride and 1, 1-dichloroethane, and the mass ratio of anhydrous aluminum chloride, 2,4, 6-trimethylbenzoyl chloride and N, N-diethylaniline is 1.01-1.5:1.01-2.5.
4. The preparation method according to claim 2, wherein in the step S2, the nonpolar organic solvent is selected from one or two of petroleum ether and cyclohexane, the mixed solvent is composed of a solvent 1 and a solvent 2, the solvent 1 is selected from one of petroleum ether and cyclohexane, the solvent 2 is selected from one of ethyl acetate, dichloromethane and methanol, and the volume ratio of the solvent 1 to the solvent 2 is 1-50:1.
5. The method for preparing a photosensitizer according to claim 1, comprising the steps of:
(1) Adding anhydrous aluminum chloride and an organic solvent D into a reaction bottle, adding 4-chlorobenzoyl chloride at a temperature of-5 ℃, stirring and reacting for 0.5-1h, adding 1,3, 5-trimethylbenzene, continuously reacting for 1-3h at a temperature of 10-25 ℃, adding the reaction solution into a hydrochloric acid aqueous solution, extracting by adopting the organic solvent D, washing an organic phase D obtained by extraction by adopting a saturated sodium bicarbonate solution, water and saturated saline in sequence, and drying to obtain an organic phase E;
(2) Filtering the organic phase E, removing the organic solvent D to obtain a solid F, adding a polar organic solvent, diethylamine and an inorganic basic compound into the solid F, carrying out reaction at a certain temperature, cooling to room temperature after the reaction is finished, adding water to separate out solid, and washing with petroleum ether to obtain the catalyst;
The reaction formula is as follows:
。
6. The preparation method according to claim 5, wherein the mass ratio of anhydrous aluminum chloride, 4-chlorobenzoyl chloride and 1,3, 5-trimethylbenzene in the step (1) is 1-2:1:1-3, the organic solvent D is one or more selected from chloroform, dichloromethane and 1, 2-dichloroethane, the mass concentration of the aqueous hydrochloric acid solution is 10-15%, and the temperature is-5 ℃.
7. The process according to claim 5, wherein the polar organic solvent in the step (2) is one or two selected from the group consisting of N, N-dimethylformamide, N-dimethylacetamide and N-methylpyrrolidone, and the inorganic basic compound is one or two selected from the group consisting of potassium carbonate, sodium carbonate, potassium hydroxide and sodium hydroxide.
8. The process according to claim 5, wherein the temperature of the reaction in step (2) is 100 to 200 ℃ and the reaction time is 12 to 24 hours.
9. The process according to claim 5, wherein the amount ratio of the substances of 4-chlorobenzoyl chloride, diethylamine and inorganic basic compound is 1:1 to 3:1 to 2, and the amount ratio of the 4-chlorobenzoyl chloride to the polar organic solvent is 1mol:50 to 100mL.
10. Use of the photosensitizer of claim 1 for the preparation of an ink.
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| CN202510045929.4A CN119431168B (en) | 2025-01-13 | A photosensitizer and its preparation method and application |
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| CN202510045929.4A CN119431168B (en) | 2025-01-13 | A photosensitizer and its preparation method and application |
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| CN104927017A (en) * | 2015-06-08 | 2015-09-23 | 中国科学技术大学 | Preparation method for double-emission waterborne polyurethane capable of emitting fluorescence and phosphorescence synchronously |
| CN110922515A (en) * | 2018-09-19 | 2020-03-27 | 北京鼎材科技有限公司 | Macromolecular photoinitiator and application and preparation method thereof |
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| CN1220734A (en) * | 1996-07-25 | 1999-06-23 | 康宁股份有限公司 | Naphthopyrans, compositions and articles comprising naphthopyrans |
| CN103788342A (en) * | 2013-12-24 | 2014-05-14 | 江苏广信感光新材料股份有限公司 | Ultraviolet-thermal dual-cured resin, anti-welding ink containing resin, and application of resin |
| CN104927017A (en) * | 2015-06-08 | 2015-09-23 | 中国科学技术大学 | Preparation method for double-emission waterborne polyurethane capable of emitting fluorescence and phosphorescence synchronously |
| CN110922515A (en) * | 2018-09-19 | 2020-03-27 | 北京鼎材科技有限公司 | Macromolecular photoinitiator and application and preparation method thereof |
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| Title |
|---|
| J.L.MATEO, P.BOSCH ET AL.: ""4-N, N-Dimethylamino-4’-Isopropylbenzo-phenone as Polymerization Photoinitiator. Effect of Solvent and Photoinitiator Concentration on Its Photoreactivity and on the Polymerization Process"", 《JOURNAL OF POLYMER SCIENCE: PART A: POLYMER CHEMISTRY》, vol. 28, 31 December 1990 (1990-12-31), pages 1445 - 1454 * |
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