CN110343081B - Fluorescent anhydride compound with aggregation-induced emission property and preparation method and application thereof - Google Patents
Fluorescent anhydride compound with aggregation-induced emission property and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a fluorescent anhydride compound with aggregation-induced emission properties, and a preparation method and application thereof. During synthesis, firstly, 4-hydroxybenzophenone or 4,4' -dihydroxybenzophenone is utilized to generate cis-trans isomeric dihydroxy tetraphenylethylene or tetrahydroxy tetraphenylethylene through McMurry coupling reaction, and the obtained tetra-styrene compound and N-methyl-4-nitrophthalimide are respectively subjected to SN reaction under the action of alkali 2 Nucleophilic reaction to produce imine compound containing tetraphenylethylene, hydrolyzing the imine compound containing tetraphenylethylene to obtain carboxylic acid compounds containing tetraphenylethylene, and dehydrating to obtain anhydride compounds. The compound has aggregation-induced emission property, has good compatibility with epoxy resin, low toxicity and high curing efficiency when being used as an epoxy resin curing agent, can be widely used for curing various epoxy resins, and the cured epoxy resin has aggregation-induced emission property and can emit strong fluorescence under ultraviolet light.
Description
Technical Field
The invention relates to preparation of a coating curing agent, in particular to a fluorescent anhydride compound with aggregation-induced emission property and a preparation method and application thereof.
Background
Because of its excellent mechanical properties, thermal stability, insulation and the like, epoxy resin is widely used in the fields of building, machinery, electronics and high technology, and is one of the most basic chemicals in the polymer resin industry at present, wherein the bisphenol A type epoxy resin has the most considerable market consumption and application prospect. The single epoxy resin has no application value, and has excellent performance only after reacting with the curing agent to form a cross-linked network structure, so that the curing agent plays a very important role in the epoxy resin. The structure and performance of the curing agent directly affect the performance and practical application of the epoxy resin system. Currently, there are three major types of epoxy resin curing agents, namely amine curing agents, acid anhydride curing agents and acid curing agents. Wherein the curing temperature of the acid curing agent is the highest. The amine curing agent can be cured at normal temperature, has mild curing conditions, and is the most widely used curing agent. The amine curing agent comprises aromatic amine, aliphatic amine, alicyclic amine, polyamide, phenolic amine and the like, and each of the amine curing agent has advantages and disadvantages. The aliphatic amines have the most varieties, high reaction activity, low viscosity and wide application (such as ethylenediamine, triethyltetramine and the like), but the aliphatic amines are volatile, toxic and pungent, and are not beneficial to health and environmental protection; the polyamide can ensure that the cured epoxy resin has good toughness, but the curing is incomplete; phenolic resins generally have a tan color, limiting their use. The anhydride curing agent is also a widely used curing agent, the viscosity of the used formula system is low, the service life is long, and the curing temperature is often required to be more than 120 ℃, so that the curing temperature is required to be reduced by adding an amine or imidazole accelerator.
Although the epoxy resin curing agents are various in types, the epoxy resin curing agents have single functions, and most of the reported curing agents only play a role in crosslinking and curing. With the diversification of the demands of people, the functions of the epoxy resin are more and more diversified, and the Chinese invention CN104449219A discloses a heat-resistant flame-retardant modified epoxy resin coating which has higher curing speed, lower curing conditions and easier operation compared with the similar flame-retardant coatings. The functional epoxy resin reported at present also comprises various functional epoxy resin coatings such as antifouling, radiation-proof, light-storing and photoluminescence coatings. The fluorescent epoxy resin paint does not emit light under natural light, can emit light with specific color under ultraviolet light, and can be used as a high-grade anti-counterfeiting material. The unique properties and broad application prospects of fluorescent epoxy resins have attracted much attention from scientists. The fluorescent epoxy resins reported so far are mainly prepared by doping a fluorescent substance such as a rare earth element or an inorganic phosphor thereto. The invention CN105385397A discloses a method for preparing luminous epoxy resin by doping fluorescent powder. Although this method can produce epoxy resin with excellent luminescence property, the phosphor or other luminescent materials are generally not compatible with epoxy resin, which not only increases the complexity of the process, but also the addition of particulate materials affects the mechanical properties of the final epoxy resin coating. The curing agent with only a single curing function cannot meet the requirement, so that the development of a new functional curing agent is urgently needed.
Disclosure of Invention
The invention aims to provide a novel fluorescent anhydride compound which is simple to synthesize, easy to prepare, low in VOC (volatile organic compound) and widely applicable to curing of various types of epoxy resins and has an aggregation-induced emission property, and a preparation method and application thereof, aiming at the current research situation of the epoxy resin curing agent. During synthesis, firstly, 4-hydroxybenzophenone or 4,4' -dihydroxybenzophenone is utilized to generate cis-trans isomeric dihydroxy tetraphenylethylene or tetrahydroxy tetraphenylethylene through McMurry coupling reaction, and the obtained tetra-styrene compound (dihydroxy tetraphenylethylene or tetrahydroxy tetraphenylethylene) and N-methyl-4-nitrophthalimide are respectively subjected to SN reaction under the action of alkali 2 Nucleophilic reaction to generate an imine compound containing tetraphenylethylene, respectively hydrolyzing the imine compound containing tetraphenylethylene to obtain carboxylic acid compounds containing tetraphenylethylene, and finally dehydrating to obtain the anhydride compounds.
The invention is realized by the following modes:
a fluorescent anhydride compound with aggregation-induced emission properties has a chemical structural formula shown as formula (I), (II) or (III):
the preparation method of the fluorescent anhydride compound with the aggregation-induced emission property comprises the following steps:
(1) synthesis of tetraphenylethylene derivatives
(a) 4-hydroxybenzophenone is subjected to coupling reaction under the action of titanium chloride and a reducing agent to obtain cis-trans isomeric dihydroxy tetraphenylethylene, after the reaction is finished, dropwise adding an alkali solution while stirring until layering is achieved, collecting an organic phase after liquid separation, adding anhydrous magnesium sulfate to dry a filtrate, performing suction filtration, performing spin drying on the filtrate to obtain a crude product, and recrystallizing to obtain a pure product;
or (b)4, 4-dihydroxy benzophenone is subjected to coupling reaction under the action of titanium chloride and a reducing agent to obtain tetrahydroxy tetraphenylethylene, after the reaction is finished, alkali solution is dropwise added while stirring until layering is achieved, an organic phase is collected after liquid separation, anhydrous magnesium sulfate is added to dry a filtrate, suction filtration is carried out, a crude product is obtained after the filtrate is dried in a spinning mode, and a pure product is obtained after recrystallization;
(2) synthesis of tetraphenylethylene-containing imine compound
SN is generated between cis-trans isomeric dihydroxy tetraphenylethylene and N-methyl-4-nitrophthalyl obtained in the step (a) under the action of alkali 2 Reacting to generate a diimine compound containing tetraphenylethylene; or the tetrahydroxytetraphenylethylene obtained in the step (b) and N-methyl-4-nitrophthaloyl generate SN under the action of alkali 2 Reacting to generate tetraimine compound containing tetraphenylethylene; the tetraphenylethylene-containing diimine compounds and tetraphenylethylene-containing tetraimine compounds are collectively referred to as tetraphenylethylene-containing imine compounds;
(3) synthesis of carboxylic acid compounds containing tetraphenylvinyl group
Hydrolyzing and acidifying an imine compound containing tetraphenylethylene under an alkaline condition respectively to obtain carboxylic acid compounds containing tetraphenylethylene;
(4) synthesis of anhydride compound containing tetraphenylethylene
The carboxylic acid compounds containing tetraphenyl vinyl are heated and dehydrated respectively to obtain the anhydride compounds containing tetraphenyl vinyl.
Further, in the step (1), the titanium chloride is titanium trichloride or titanium tetrachloride, the reducing agent is one of sodium, potassium, zinc or magnesium, the base is potassium carbonate or sodium carbonate, and the reaction condition is heating reflux.
Further, in the step (1), a solvent is used for the reaction, and the solvent is tetrahydrofuran.
Further, in the step (2), the alkali is potassium carbonate, sodium carbonate or potassium bicarbonate, and the reaction condition is heating reflux.
Further, in the step (2), a solvent is used for the reaction, and the solvent is DMF or DMSO.
Further, in the step (3), the alkali is sodium hydroxide, potassium carbonate or ammonium chloride, the acid is hydrochloric acid or sulfuric acid, and the reaction condition is heating reflux.
Further, in the step (3), a solvent is used for the reaction, and the solvent is water.
Further, in the step (4), dehydration is carried out with P 2 O 5 Or (CH) 3 CO) 2 O is dehydrating agent, and the reaction condition is heating reflux.
The fluorescent anhydride compound with aggregation-induced emission property is used as a curing agent, and can be used alone, or used by mixing more than two of the fluorescent anhydride compounds, or used by mixing with other curing agents.
The invention has the beneficial effects that:
the compound has aggregation-induced emission property, when the compound is used as an epoxy resin curing agent, the curing agent has good compatibility with epoxy resin, low toxicity and high curing efficiency, can be widely used for curing various epoxy resins, can be used independently or by mixing two or more curing agents, can also be used by mixing with other various curing agents, and the cured epoxy resin has aggregation-induced emission property, can emit strong fluorescence under ultraviolet light, can be applied to the field of high-grade anti-counterfeiting coatings, and widens the application of the epoxy resin.
Drawings
FIG. 1 is a nuclear magnetic diagram of the dianhydride compound of example 1.
FIG. 2 is a mass spectrum of the dianhydride compound of example 1.
FIG. 3 is a photograph of fluorescence emission of dianhydride compound of example 1 in pure DMF and mixed solvent of DMF and petroleum ether (petroleum ether volume fraction is 90%) under 365nm ultraviolet light (solution concentration is 0.01mg/mL), which has significant aggregation-induced emission property.
Detailed Description
The present invention is further illustrated by the following examples, which are intended to be illustrative only and are not to be construed as limiting the scope of the invention, which is to be construed as being limited thereby.
Example 1
1. Synthesis of tetraphenylethylene derivatives
4-hydroxybenzophenone (0.2mol,40.0g) and zinc powder (0.4mol,25.9g) were charged into a 1000mL four-necked flask, and under a closed condition, oxygen and nitrogen were repeatedly purged three times, 600mL of purified THF was then added, titanium tetrachloride (0.3mol,32.75mL) was slowly added dropwise under stirring at-30 ℃ and after completion of addition, stirring was carried out at room temperature for 1 hour, followed by stirring at 90 ℃ for reflux reaction for 12 hours. Stopping heating after the reaction is finished, pouring the reaction solution into a 2L beaker after the reaction solution is cooled, dropwise adding a potassium carbonate solution with the mass fraction of 10% while stirring until the solution is layered, separating the solution, and using dichloromethane for three times to obtain filtrate; the organic phase was dried over anhydrous magnesium sulfate for 4h and filtered, and the filtrate was spin-dried to give the crude product. The crude product was dried, washed with toluene: recrystallization from petroleum ether at 4:1 gave a pale yellow solid.
2. Synthesis of imino compound containing tetraphenyl vinyl
Tetraphenylethenyl derivative (0.05mol,11.4g), p-chloronitrobenzene (0.11mol,17.27g) and K 2 CO 3 (0.15mol,20.73g) and DMF (150mL) were charged into a 250mL four-necked flask equipped with a water separator, a condenser, a thermometer and a stirring device, and the mixture was heated to reflux with stirring under nitrogen protection to react for 8 hours. Cooling and pouring into waterObtaining yellow precipitate, and obtaining a crude product after suction filtration, water washing and drying. The crude product is recrystallized by a mixed solvent of toluene and petroleum ether to obtain a pure product.
3. Synthesis of carboxylic acid compounds containing tetraphenylvinyl group
Sequentially adding 0.05mol of diimine compound containing tetraphenyl vinyl (32.8 g), (0.5mol of 28g) and 500mL of water into a 1000mL four-neck flask with a condenser and a stirring device, heating to 100 ℃ under the condition of mechanical stirring, carrying out reflux reaction until no ammonia gas is generated, stopping the reaction, adding hydrochloric acid into the reaction liquid until the pH value is less than 2 after the reaction system is cooled to room temperature, continuously stirring for 12h, filtering, collecting the product, and drying to obtain the target product.
4. Synthesis of anhydride compound containing tetraphenylvinyl group
Adding a carboxylic acid compound containing tetraphenyl vinyl (0.05mol,32.8g) and 200mL of acetic anhydride into a 500mL four-neck flask with a condenser and a stirrer, heating under mechanical stirring and refluxing until the reaction system forms a uniform solution, filtering, cooling and crystallizing to obtain the target product.
5. Tetraphenylethylene-containing anhydride compound cured epoxy resin
Mixing epoxy resin E-44 (epoxy value of 0.4-0.47) and the above tetraphenyl vinyl group-containing acid anhydride compound at a mass ratio of 1:0.6, stirring to homogenize, standing for aging to remove gas mixed by stirring. And placing the mixture in a ceramic crucible, placing the ceramic crucible in a forced air drying oven, and placing for 24 hours at 50 ℃ to obtain the cured epoxy resin. And (3) respectively placing the cured epoxy resin under natural light and a 360nm ultraviolet lamp for observation, wherein the cured epoxy resin does not emit light under the natural light, and the cured epoxy resin emits blue-green fluorescence under the ultraviolet lamp.
Example 2
The mixture of the tetraphenylethylene-containing anhydride compound obtained in example 1 and diaminodiphenylmethane (mass ratio 1:1) was mixed with an epoxy resin E-44 (epoxy value of 0.4 to 0.47) in a ratio of 0.6: 1, stirring to be uniform, standing and ageing to remove gas mixed in by stirring. And placing the mixture in a ceramic crucible, placing the ceramic crucible in a forced air drying oven, and placing for 24 hours at 50 ℃ to obtain the cured epoxy resin. And respectively placing the cured epoxy resin under natural light and a 360nm ultraviolet lamp for observation, wherein the cured epoxy resin does not emit light under the natural light, and the cured epoxy resin emits blue-green fluorescence under the ultraviolet lamp.
Claims (7)
1. A preparation method of a fluorescent anhydride compound with aggregation-induced emission properties is provided, wherein the fluorescent anhydride compound with aggregation-induced emission properties is used as a curing agent, and the chemical structural formula of the fluorescent anhydride compound with aggregation-induced emission properties is shown as formula (I), (II) or (III):
the preparation method of the fluorescent anhydride compound with aggregation-induced emission property comprises the following steps:
(1) synthesis of tetraphenylethylene derivatives
(a) 4-hydroxybenzophenone is subjected to coupling reaction under the action of titanium chloride and a reducing agent to obtain cis-trans isomeric dihydroxy tetraphenylethylene, after the reaction is finished, dropwise adding an alkali solution while stirring until layering is achieved, collecting an organic phase after liquid separation, adding anhydrous magnesium sulfate to dry a filtrate, performing suction filtration, performing spin drying on the filtrate to obtain a crude product, and recrystallizing to obtain a pure product;
or (b) carrying out coupling reaction on 4, 4-dihydroxy benzophenone under the action of titanium chloride and a reducing agent to obtain tetrahydroxy tetraphenylethylene, after the reaction is finished, dropwise adding an alkali solution while stirring until layering is carried out, collecting an organic phase after liquid separation, adding anhydrous magnesium sulfate to dry a filtrate, carrying out suction filtration, carrying out spin drying on the filtrate to obtain a crude product, and recrystallizing to obtain a pure product;
(2) synthesis of tetraphenylethylene-containing imine compound
SN is generated between cis-trans isomeric dihydroxy tetraphenylethylene and N-methyl-4-nitrophthaloyl obtained in step (a) under the action of alkali 2 Reacting to form a diimine compound containing tetraphenylethylene(ii) a Or the tetrahydroxy tetraphenylethylene obtained in the step (b) and N-methyl-4-nitrophthalyl generate SN under the action of alkali 2 Reacting to generate tetraimine compound containing tetraphenylethylene; the tetraphenylethylene-containing diimine compounds and tetraphenylethylene-containing tetraimine compounds are collectively referred to as tetraphenylethylene-containing imine compounds;
(3) synthesis of carboxylic acid compounds containing tetraphenylvinyl group
Hydrolyzing and acidifying the tetraphenylethylene-containing imine compound under alkaline conditions respectively to obtain a tetraphenylethylene-containing carboxylic acid compound;
(4) synthesis of tetraphenylethylene-containing anhydride compound
The carboxylic acid compounds containing the tetraphenyl vinyl group are respectively heated and dehydrated to obtain anhydride compounds containing the tetraphenyl vinyl group;
in the step (1), the titanium chloride is titanium trichloride or titanium tetrachloride, the reducing agent is one of sodium, potassium, zinc or magnesium, the alkali is potassium carbonate or sodium carbonate, and the reaction condition is heating reflux.
2. The method for preparing a fluorescent anhydride compound with an aggregation-induced emission property according to claim 1, wherein a solvent is used in the reaction in the step (1), and the solvent is tetrahydrofuran.
3. The method for preparing a fluorescent anhydride compound with aggregation-induced emission property according to claim 1, wherein in the step (2), the base is potassium carbonate, sodium carbonate or potassium bicarbonate, and the reaction condition is heating reflux.
4. The method for preparing a fluorescent anhydride compound with aggregation-induced emission properties according to claim 1, wherein in the step (2), a solvent is used for the reaction, and the solvent is DMF or DMSO.
5. The method for preparing a fluorescent anhydride compound with aggregation-induced emission property according to claim 1, wherein in the step (3), the base is sodium hydroxide, potassium carbonate or ammonium chloride, the acid is hydrochloric acid or sulfuric acid, and the reaction condition is heating reflux reaction.
6. The method for preparing a fluorescent anhydride compound with aggregation-induced emission properties according to claim 1, wherein a solvent is used in the reaction in the step (3), and the solvent is water.
7. The method for preparing fluorescent anhydride compound having aggregation-induced emission property according to claim 1, wherein in the step (4), dehydration is performed with P 2 O 5 Or (CH) 3 CO) 2 O is dehydrating agent, and the reaction condition is heating reflux.
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3479320A (en) * | 1968-06-24 | 1969-11-18 | Gen Electric | Polymerization of cyclic organosiloxanes with group ii-a metal complexes |
| CN1340067A (en) * | 1999-02-16 | 2002-03-13 | 荷兰解决方案研究有限公司 | Process for producing phenol-dicarbonyl condensates with increased fluorescence, epoxy resins, epoxy resin systems and laminates made with the same |
| CN103937158A (en) * | 2014-03-24 | 2014-07-23 | 北京化工大学 | Quantum dot with high transparency and high fluorescence efficiency/epoxy resin nano composite material, preparation and applications thereof |
| CN106008920A (en) * | 2016-06-26 | 2016-10-12 | 苏州吉人高新材料股份有限公司 | Modified epoxy resin with fluorescent characteristic and preparation method thereof |
| CN106867507A (en) * | 2016-12-27 | 2017-06-20 | 广东阿格蕾雅光电材料有限公司 | A kind of green glow dyestuff with aggregation-induced emission property |
| CN106883720A (en) * | 2017-03-13 | 2017-06-23 | 苏州吉人高新材料股份有限公司 | A kind of water-base epoxy dispersion with fluorescent effect and preparation method thereof |
| CN109233738A (en) * | 2018-08-31 | 2019-01-18 | 江苏科技大学 | Fluorescence adhesive and the preparation method and application thereof based on aggregation-induced emission mechanism |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103951943A (en) * | 2014-04-30 | 2014-07-30 | 中国科学院深圳先进技术研究院 | Insulating resin composition and preparation method thereof |
-
2019
- 2019-07-31 CN CN201910702870.6A patent/CN110343081B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3479320A (en) * | 1968-06-24 | 1969-11-18 | Gen Electric | Polymerization of cyclic organosiloxanes with group ii-a metal complexes |
| CN1340067A (en) * | 1999-02-16 | 2002-03-13 | 荷兰解决方案研究有限公司 | Process for producing phenol-dicarbonyl condensates with increased fluorescence, epoxy resins, epoxy resin systems and laminates made with the same |
| CN103937158A (en) * | 2014-03-24 | 2014-07-23 | 北京化工大学 | Quantum dot with high transparency and high fluorescence efficiency/epoxy resin nano composite material, preparation and applications thereof |
| CN106008920A (en) * | 2016-06-26 | 2016-10-12 | 苏州吉人高新材料股份有限公司 | Modified epoxy resin with fluorescent characteristic and preparation method thereof |
| CN106867507A (en) * | 2016-12-27 | 2017-06-20 | 广东阿格蕾雅光电材料有限公司 | A kind of green glow dyestuff with aggregation-induced emission property |
| CN106883720A (en) * | 2017-03-13 | 2017-06-23 | 苏州吉人高新材料股份有限公司 | A kind of water-base epoxy dispersion with fluorescent effect and preparation method thereof |
| CN109233738A (en) * | 2018-08-31 | 2019-01-18 | 江苏科技大学 | Fluorescence adhesive and the preparation method and application thereof based on aggregation-induced emission mechanism |
Non-Patent Citations (3)
| Title |
|---|
| 《Studying a novel AIE coating and its handling process via fluorescence spectrum》;Weili Li等;《RSC Adv》;20171231;第7卷;摘要、方案图1、图2 * |
| 《The synthesis of a 1,l’-bi-2-naphthol-based bis(ether anhydride) and aromatic polyamidesderived therefrom》;Qiding Mi等;《Polymer》;19971231;第38卷(第14期);实验部分 * |
| 《基于具有聚集诱导发光特性的四苯乙烯分子而构建的新型荧光分子探针的研究》;王晓晶;《中国优秀硕士学位论文全文数据库 工程科技I辑》;20160215(第02期);摘要、第2.2.3节、第3.2.4节 * |
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