CN120118110A - Preparation of a bromine-containing seven-membered fluorine boron compound and its application in fluorescent ink - Google Patents
Preparation of a bromine-containing seven-membered fluorine boron compound and its application in fluorescent ink Download PDFInfo
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- CN120118110A CN120118110A CN202510448857.8A CN202510448857A CN120118110A CN 120118110 A CN120118110 A CN 120118110A CN 202510448857 A CN202510448857 A CN 202510448857A CN 120118110 A CN120118110 A CN 120118110A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/16—Writing inks
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/50—Sympathetic, colour changing or similar inks
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
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Abstract
本发明公开了一种含溴七元氟硼化合物的制备及其在荧光墨水上的应用，以2,3,3‑三甲基吲哚与5‑甲酰基‑2,4‑二甲基‑1H‑吡咯‑3‑羧酸乙酯为原料，在醋酸、哌啶、甲苯的作用下，经Knoevenagel缩合反应，生成一种七元氟硼荧光染料，将这种七元氟硼荧光染料与NBS发生自由基反应，生成一种创新型结构。该化合物在一些溶液中荧光量子产率高，将该化合物溶于丙烯酸树脂的正丁醇溶液，可用作荧光墨水，作用于硫酸纸、玻璃板等材料，具有较高的隐蔽性且简单易得。
The invention discloses the preparation of a bromine-containing seven-membered fluoroboron compound and its application in fluorescent ink, using 2,3,3-trimethylindole and 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester as raw materials, under the action of acetic acid, piperidine and toluene, through Knoevenagel condensation reaction, a seven-membered fluoroboron fluorescent dye is generated, and this seven-membered fluoroboron fluorescent dye is subjected to free radical reaction with NBS to generate an innovative structure. The compound has a high fluorescence quantum yield in some solutions, and the compound is dissolved in a n-butanol solution of acrylic resin, which can be used as a fluorescent ink, acting on materials such as sulfuric acid paper and glass plates, with high concealment and easy to obtain.
Description
Technical Field
The invention relates to the technical field of materials, in particular to preparation of a novel bromine-containing seven-membered boron fluoride compound, which has higher fluorescence quantum yield and can be widely applied to the field of fluorescent ink.
Background
Fluorescent inks contain fluorescent agents that produce a fluorescent effect when exposed to ultraviolet light (365 nm) (e.g., ultraviolet light from sunlight, fluorescent lamps, mercury lamps, etc.). The key principle is that visible fluorescent compounds with ultraviolet excitation are added into the ink, and after absorbing light energy, the compounds generate energy level transition of atoms and release absorbed extra energy, so that visible light with red, yellow, green, blue and the like can be emitted. Such inks are often used to increase the security of documents or products, such as currency, passports, tickets and other items requiring anti-counterfeiting measures. Fluorescent inks come in a variety of colors, commonly known as yellow-green, orange-red, blue-green, etc., which are barely visible under normal light, but which appear brightly fluorescent under ultraviolet light.
The fluorescent ink has high brightness, can generate strong visual impact, has high color saturation, is vivid and lasting, does not fade, can increase visual layering and stereoscopic impression of printed matters, makes patterns or characters more vivid and attractive, has high transparency, and is suitable for covering printing to form unique visual effects.
The fluorescent ink is not only applied to commercial advertisements, but also widely applied to decoration printing and safety identification, and is beneficial to improving the visibility and the identification degree of the identification. In addition, due to the concealment and the convertibility, the fluorescent ink has important application in the anti-counterfeiting printing field, and special fluorescent patterns or characters can be displayed through ultraviolet irradiation, so that anti-counterfeiting detection is realized. When using fluorescent inks, special care is required for their compatibility with the print medium or coating layer to ensure optimal fluorescence effect and lifetime.
Disclosure of Invention
The invention provides a preparation method of a bromine-containing seven-membered boron fluoride compound and application research of the bromine-containing seven-membered boron fluoride compound in fluorescent ink. The compound is simple and easy to obtain, low in manufacturing cost, high in fluorescence quantum yield and small in environmental pollution.
Bromine-containing seven-membered boron fluoride compound and application thereof in fluorescent ink, wherein the chemical structural formula of the compound is as follows:
the synthesis method for synthesizing the bromine-containing seven-membered boron fluoride compound comprises the following synthesis paths:
The method specifically comprises the following steps:
(1) Adding a compound 1, namely 2, 3-trimethyl indole, and a compound 2, namely 5-formyl-2, 4-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester toluene into a reaction bottle at room temperature, dissolving, then sequentially adding piperidine and acetic acid, and heating to 120 ℃ for reaction to obtain a reaction solution;
(2) Removing toluene from the reaction liquid in the step (1) by rotary evaporation, and separating by silica gel column chromatography to obtain a solid product 3;
(3) Sequentially adding the compound 3, NBS and AlCl 3 obtained in the step (2) into a reaction bottle, and finally adding chloroform for ultrasonic dissolution to react to obtain a reaction solution;
(4) And (3) removing solvent chloroform by rotary evaporation of the reaction liquid in the step (3), and separating by silica gel column chromatography to obtain a solid product I, namely the bromine-containing seven-membered boron fluoride compound.
The compound 3 is a seven-membered boron fluoride compound, the compound I is a bromine-containing seven-membered boron fluoride compound, the feeding ratio of the compound 3 to NBS is 1:1-2, and the feeding ratio of the compound 3 to AlCl 3 is 1:0.5-2.
The feeding sequence of the step (1) is that the compound 1, the compound 2, toluene, acetic acid and piperidine are used as catalysts and are added at last.
The feeding sequence of the step (3) is that the compound 3, NBS and AlCl 3 are dissolved in chloroform.
The heating temperature of the step (1) is 120 ℃, the heating time is 2.5 hours, the reaction temperature of the step (3) is 0-40 ℃, and the heating time is 10 minutes-1 hour.
The invention also provides an application of the bromine-containing seven-membered boron fluoride compound as fluorescent ink.
Specifically, after acrylic resin is dispersed in n-butanol solution, the bromine-containing seven-membered boron fluoride compound is added to obtain fluorescent ink, and the fluorescent ink is coated on a substrate and has a fluorescent effect under ultraviolet light.
The adding amount of the bromine-containing seven-membered boron fluoride compound is 1.0% -1.5%.
The ultraviolet light is an ultraviolet light source of 365nm-380nm, and the substrate comprises any one of paper, steel plate, wood, A4 paper and glass material.
The invention has the following beneficial effects:
(1) The bromine-containing seven-membered boron fluoride compound synthesized by the invention has high fluorescence quantum yield, is simple and easy to obtain, and has low manufacturing cost and low pollution.
(2) The bromine-containing seven-membered boron fluoride compound has great potential in the field of fluorescent ink, and has obvious fluorescent effect when the mass ratio of fluorescent powder is 1.0% -1.5%.
Drawings
FIG. 1 is a hydrogen spectrum of compound 3 obtained in example 1.
FIG. 2 is a hydrogen spectrum of compound I obtained in example 3.
FIG. 3 is a clear fluorescent image obtained by photographing a fluorescent ink prepared by the compound I of example 10-1 with a nova 12 mobile phone under natural light and under an ultraviolet lamp (365 nm) after the fluorescent ink acts on a piece of parchment paper.
FIG. 4 is a clear fluorescent image obtained by photographing a fluorescent ink prepared by the compound I of example 10-2 with a nova 12 mobile phone under natural light and under an ultraviolet lamp (365 nm) after the fluorescent ink acts on a piece of parchment paper.
FIG. 5 is a clear fluorescent image obtained by photographing a fluorescent ink prepared by the compound I of example 10-3 on a piece of parchment paper under natural light and under an ultraviolet lamp (365 nm) with a Hua-Cheva 12 mobile phone.
FIG. 6 is a clear fluorescent image obtained by photographing a fluorescent ink prepared by the compound I of example 10-4 on a piece of parchment paper under natural light and under an ultraviolet lamp (365 nm) with a Hua-Cheva 12 mobile phone.
FIG. 7 is a clear fluorescent image obtained by photographing a fluorescent ink prepared in example 10-5 with a nova 12 mobile phone under natural light and under an ultraviolet lamp (365 nm) after the fluorescent ink acts on a piece of parchment paper.
FIG. 8 is a clear fluorescent image of the fluorescent ink prepared in example 10-2 after the fluorescent ink acts on the parchment paper, and a clear fluorescent image comparison of the fluorescent ink prepared in the patent "preparation of a phosphorus-containing seven-membered boron fluoride compound and its application in fluorescent ink".
Detailed Description
The present invention will be further illustrated by the following examples, but the scope of the invention is not limited to the examples.
Example 1
2, 3-Trimethylindole (573 mg,3.6 mmol), 5-formyl-2, 4-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester (585 mg,3 mmol) were weighed, 15mL of toluene was taken and dissolved, piperidine (297. Mu.L, 3 mmol), acetic acid (171. Mu.L, 3 mmol) were added sequentially, and reacted at 120℃for 2.5 hours, cooled to room temperature and then toluene was removed by rotary evaporation, finally silica gel column chromatography gave compound 3 as a yellow solid in 63.7% yield.
。
Example 2
Compound 3 seven-membered boron fluoride fluorescent dye (463.9 mg,1 mmol) was weighed, dissolved in 5.00mL of chloroform, then NBS (178 mg,1 mmol) and AlCl 3 (66.5 mg,0.5 mmol) were added sequentially, and the reaction was stirred at room temperature for 1 hour and completed. The reaction was extracted and then distilled off in a rotary column, and the red solid compound I was obtained after column chromatography in a yield of 56.5%.
。
Example 3
The compound 3 seven-membered boron fluoride fluorescent dye (463.9 mg,1 mmol) was weighed, 5.00mL of chloroform was taken and dissolved, NBS (178 mg,1 mmol), alCl 3 (133 mg,1 mmol) and 10mL of chloroform were sequentially added, and after ultrasonic dissolution, the reaction was stirred at room temperature for 40 minutes, and the reaction was completed. The reaction product is extracted and then rotary distilled, and the product is obtained after column chromatography. Compared with example 2, the catalyst was increased by 0.5 times equivalent, the reaction time was shortened by 30 minutes, and the yield was increased by 11.7%.
。
Example 4
The compound 3 seven-membered boron fluoride fluorescent dye (463.9 mg,1 mmol) was weighed, 5.00mL of chloroform was taken and dissolved, NBS (178 mg,1 mmol), alCl 3 (266 mg,2 mmol) and 10mL of chloroform were sequentially added, and after ultrasonic dissolution, the reaction was stirred at room temperature for 0.5 hour and completed. The reaction product is extracted and then rotary distilled, and the product is obtained after column chromatography. Compared with example 3, alCl 3 has double equivalent, the reaction time is shortened by ten minutes, the yield is not great, but obvious carbonization is realized.
。
Example 5
The compound 3 seven-membered boron fluoride fluorescent dye (463.9 mg,1 mmol) was weighed, 5.00mL of chloroform was taken and dissolved, NBS (178 mg,1 mmol), alCl 3 (133 mg,1 mmol) and 10mL of chloroform were sequentially added, and after ultrasonic dissolution, the reaction was stirred at 0 ℃ for 1 hour and was incomplete. The reaction product is extracted and then is distilled in a rotary way, and the compound I is obtained after column chromatography. Compared with example 3, the reaction temperature was 0 ℃ and the ice bath condition affected the reaction rate, so the yield was reduced by 21.8%.
。
Example 6
The compound 3 seven-membered boron fluoride fluorescent dye (463.9 mg,1 mmol) was weighed, 5.00mL of chloroform was taken and dissolved, NBS (178 mg,1 mmol), alCl 3 (133 mg,1 mmol) and 10mL of chloroform were sequentially added, and after ultrasonic dissolution, the reaction was stirred at 40℃for 0.5 hour and completed. The reaction was extracted and then distilled by spin distillation, followed by column chromatography to give compound I as a red solid. Compared with example 3, the temperature is increased by 15 ℃, carbonization is carried out after the heating reaction, and the yield is reduced by 11.4%.
。
Example 7
The compound 3 seven-membered boron fluoride fluorescent dye (463.9 mg,1 mmol) was weighed, 5.00mL of chloroform was taken and dissolved, then NBS (356 mg,2 mmol), alCl 3 (133 mg,1 mmol) and 10mL of chloroform were sequentially added, and after ultrasonic dissolution, the reaction was stirred at room temperature for 10 minutes and completed. The reaction was extracted and then distilled by spin-on, followed by column chromatography to give a red solid. Compared with example 3, the equivalent ratio of NBS is doubled, byproducts are increased, the reaction time is shortened by 20 minutes, and the yield is reduced by 36%.
。
Example 8
The compound 3 seven-membered boron fluoride fluorescent dye (463.9 mg,1 mmol) was weighed, 5.00mL of chloroform was taken and dissolved, then NBS (356 mg,1 mmol), alCl 3 (133 mg,1 mmol) and 20mL of chloroform were sequentially added, and after ultrasonic dissolution, the reaction was stirred at room temperature for 50 minutes, and the reaction was completed. The reaction was extracted and then distilled by spin-on, followed by column chromatography to give a red solid. Compared with example 3, the solvent was increased by 5mL, the reaction time was prolonged by 20 minutes, and the yield was reduced by 8.1%.
。
Example 9
The compound 3-heptafluoro-boron fluorescent dye (463.9 mg,1 mmol) was weighed, 5.00mL of chloroform was dissolved, NBS (356 mg,1 mmol), alCl 3 (133 mg,1 mmol) and 5mL of chloroform were added sequentially, and the mixture was dissolved by ultrasonic wave, and then stirred at room temperature for reaction for 1 hour. The reaction was extracted and then distilled by spin-on, followed by column chromatography to give a red solid. Compared with example 3, the solvent is reduced by 5mL, the dissolution is insufficient, the reaction is incomplete, the reaction time is prolonged by 40 minutes, and the yield is reduced by 39.3%.
。
Example 10 preparation of fluorescent ink
Example 10-1
Acrylic resin (30 mg) is uniformly dispersed in n-butyl alcohol (290 mg), stirred under magnetic stirring until the acrylic resin is completely dissolved, and kept stand for 10 minutes to form a uniformly dispersed carrier, then compound I (2 mg) is added, and after being pre-dispersed for 30 minutes on a magnetic electric stirrer, the required color paste is obtained through high-speed stirring. The color paste was applied to the coated paper, and the coated paper was photographed under natural light and ultraviolet light (365 nm) using Hua for nova 12 to obtain FIG. 3, and it can be seen that the fluorescent effect was clear under the natural light (left) and under the ultraviolet light (right) at 365 nm.
Example 10-2
Acrylic resin (30 mg) is uniformly dispersed in n-butyl alcohol (290 mg), stirred under magnetic stirring until the acrylic resin is completely dissolved, and kept stand for 10 minutes to form a uniformly dispersed carrier, then compound I (4 mg) is added, and after being pre-dispersed for 30 minutes on a magnetic electric stirrer, the required color paste is obtained through high-speed stirring. The color paste was applied to the kraft paper, and was photographed under natural light and ultraviolet lamp (365 nm) using nova 12 to obtain fig. 4, and it can be seen that the fluorescent effect was clearly seen under natural light (left) and under ultraviolet light (right) at 365 nm.
Example 10-3
Acrylic resin (30 mg) was uniformly dispersed in n-butanol (290 mg), stirred under magnetic stirring until completely dissolved, allowed to stand for 10 minutes to form a uniformly dispersed carrier, then compound I (8 mg) was added, and after 30 minutes of pre-dispersion on a magnetic stirrer, stirred at high speed to obtain the desired color paste. The color paste was applied to the kraft paper, and was photographed under natural light and ultraviolet lamp (365 nm) using nova 12 to obtain fig. 5, and it can be seen that the fluorescent effect was clearly seen under natural light (left) and under ultraviolet light (right) at 365 nm.
Examples 10 to 4
Acrylic resin (30 mg) was uniformly dispersed in n-butanol (290 mg), stirred under magnetic stirring until completely dissolved, allowed to stand for 10 minutes to form a uniformly dispersed carrier, then compound I (16 mg) was added, and after 30 minutes of pre-dispersion on a magnetic stirrer, stirred at high speed to obtain the desired color paste. The color paste was applied to the kraft paper, and was photographed under natural light and ultraviolet lamp (365 nm) using Hua for nova 12 to obtain fig. 6, and it can be seen that the fluorescent effect was clearly seen under the natural light (left) and under the ultraviolet light (right) of 365 nm.
Comparison of examples 10-1, 10-2, 10-3 and 10-4 shows that the effect is optimal when the mass ratio of the fluorescent powder is 1.0% -1.5%, the mass of the fluorescent powder is less, the fluorescence of the example 10-1 and the right graph is weaker, the fluorescent powder is sequentially amplified by two times, the fluorescent powder is the strongest in the right graph of the example 10-2, and after the mass of the fluorescent powder is continuously amplified by two times or even four times, the fluorescent powder is weakened in the right graphs of the figures 5 and 6 due to the effect of fluorescence inhibition, but the effect of the example 10-2 is not obvious.
Examples 10 to 5
Acrylic resin (30 mg) was uniformly dispersed in n-butanol (290 mg), stirred under magnetic stirring until completely dissolved, allowed to stand for 10 minutes to form a uniformly dispersed carrier, then compound 3 (4 mg) was added, and after 30 minutes of pre-dispersion on a magnetic stirrer, stirred at a high speed to obtain the desired color paste. When the obtained color paste was applied to the kraft paper, it can be seen that the color paste has no fluorescence effect under natural light, and the fluorescence effect can be clearly seen under 365nm ultraviolet light as shown in fig. 7.
Examples 10 to 6
The compounds I-1, I-2 and I-3 have stronger fluorescence effect compared with the patent 'preparation of phosphorus-containing seven-element fluorine boron compound and application thereof in fluorescent ink', and are shown in figure 8.
The fluorescent ink can be obtained by the embodiment mode of the 2 compounds. The fluorescent ink prepared by the method can also be applied to materials such as steel plates, wood, A4 paper, glass and the like.
The above embodiments are merely preferred embodiments of the present application, and should not be construed as limiting the present application, and the embodiments and features of the embodiments of the present application may be arbitrarily combined with each other without collision. The protection scope of the present application is defined by the claims, and the protection scope includes equivalent alternatives to the technical features of the claims. I.e., equivalent replacement modifications within the scope of this application are also within the scope of the application.
Claims (10)
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