CN111206288A - Fluorescent aramid fiber based on aggregation-induced emission and preparation and application thereof - Google Patents
Fluorescent aramid fiber based on aggregation-induced emission and preparation and application thereof Download PDFInfo
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- CN111206288A CN111206288A CN202010055248.3A CN202010055248A CN111206288A CN 111206288 A CN111206288 A CN 111206288A CN 202010055248 A CN202010055248 A CN 202010055248A CN 111206288 A CN111206288 A CN 111206288A
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- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F1/00—General methods for the manufacture of artificial filaments or the like
- D01F1/02—Addition of substances to the spinning solution or to the melt
- D01F1/06—Dyes
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/14—Styryl dyes
- C09B23/143—Styryl dyes the ethylene chain carrying a COOH or a functionally modified derivative, e.g.-CN, -COR, -COOR, -CON=, C6H5-CH=C-CN
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- 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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- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/88—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds
- D01F6/90—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds of polyamides
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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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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Abstract
The invention relates to a preparation method of a fluorescent aramid fiber based on aggregation-induced emission, which comprises the following steps: the method comprises the steps of adopting a micro-fluidic spinning method, taking an aramid spinning solution as an internal phase solution, wherein the aramid spinning solution comprises a fluorescent dye with aggregation-induced emission effect and aramid, taking a mixed solution of an organic solvent and water as an external phase solution, and injecting the internal phase solution into the external phase solution to solidify the obtained fiber to obtain the fluorescent aramid fiber based on aggregation-induced emission. The method has the advantages of simple process, mild conditions, safety and energy conservation, and the prepared fluorescent aramid fiber has high fluorescence efficiency, good stability and good fluorescence durability.
Description
Technical Field
The invention relates to the technical field of fiber preparation, in particular to a fluorescent aramid fiber based on aggregation-induced emission and preparation and application thereof.
Background
However, most of the traditional organic luminescent materials only emit light in solution, when the materials are in a powder or thin film state, the fluorescence intensity can be rapidly reduced or directly quenched, and the Aggregation-induced Quenching (Aggregation-Quenching ACQ) greatly limits the application of the organic luminescent materials. Since the concept of Aggregation-Induced Emission AIE (Aggregation-Induced Emission AIE) was proposed in 2001, more and more organic molecules with AIE effect enter the visual field of people, do not emit light in solution, but emit bright fluorescence during Aggregation, so that the ACQ problem is fundamentally solved, and a new idea is opened for the development of the field of photoelectric materials in the future.
The traditional fiber preparation technologies comprise melt spinning, wet spinning, electrostatic spinning and the like, although the methods are relatively mature spinning technologies at present, the preparation process usually needs spinning conditions with high energy consumption, such as high temperature and high pressure, the use of a large amount of organic solvents and the like, and the operation environment is severe, so that the method is not beneficial to physical and psychological health of workers.
The fluorescent fiber is difficult to prepare at present, low in fluorescence intensity and easy to quench. Therefore, the problem to be solved at present is to find a spinning method with simple equipment, convenient operation process and mild spinning conditions to prepare the fluorescent fiber with excellent performance.
Disclosure of Invention
In order to solve the technical problems, the invention aims to provide the fluorescent aramid fiber based on aggregation-induced emission and the preparation and application thereof.
The invention relates to a preparation method of a fluorescent aramid fiber based on aggregation-induced emission, which comprises the following steps:
the method comprises the steps of adopting a micro-fluidic spinning method, taking an aramid spinning solution as an internal phase solution, wherein the aramid spinning solution comprises a fluorescent dye with aggregation-induced emission effect and aramid, taking a mixed solution of an organic solvent and water as an external phase solution, and injecting the internal phase solution into the external phase solution to solidify the obtained fiber to obtain the fluorescent aramid fiber based on aggregation-induced emission.
Further, the fluorescent dye having aggregation-induced emission effect includes a compound having one or more of the following structural formulas:
preferably, the fluorescent dye having aggregation-induced emission effect has the following structural formula:
① at room temperature, reacting hydroxybenzyl acetonitrile with 3, 4-dihydro-2H-pyran to obtain compound 1;
② reacting the compound 1 with 1-naphthaldehyde under heating reflux to obtain a compound 2;
③ reacting the compound 2 with concentrated hydrochloric acid at room temperature to obtain the target compound, wherein the preparation route is as follows:
preferably, the molar ratio of the p-hydroxyphenylacetonitrile to the 3, 4-dihydro-2H-pyran in step ① is 1:1, and the reaction time is 24H.
Preferably, the molar ratio of the compound 1 to the 1-pyrenecarboxaldehyde in the step ② is 1:1, and stirring and refluxing are carried out at 65 ℃ for 12 h.
Preferably, the reaction time in the step ③ is 12-15 h, and after the reaction is finished, purified by pure water.
Furthermore, in the aramid fiber spinning solution, the mass fraction of the fluorescent dye with aggregation-induced emission effect is 0.1-0.5%.
Furthermore, in the aramid fiber spinning solution, the mass fraction of aramid fiber is 10-12%.
Further, the solvent in the aramid spinning solution comprises one or more of N 'N-dimethylacetamide, N' N-dimethylformamide and dimethyl sulfoxide; the organic solvent in the external phase solution comprises one or more of N 'N-dimethylacetamide, N' N-dimethylformamide and dimethyl sulfoxide.
Furthermore, the volume ratio of the organic solvent to the water in the external phase solution is 3-7: 3-7. Preferably, the volume ratio of organic solvent to water is 3:7, 4:6, 5:5, 6:4 or 7: 3.
Further, the microfluidic spinning method is carried out by adopting a microfluidic device, the microfluidic device comprises an inner phase channel for containing the inner phase solution and an outer phase channel for containing the outer phase solution, and the inner diameter ratio of the inner phase channel to the outer phase channel is 1-1.8: 6-8.
Preferably, the inner phase channel has an inner diameter of 100 to 150 μm.
Furthermore, the flow rate of the inner phase solution is 2-20 muL/min, and the flow rate of the outer phase solution is 50-550 muL/min.
The invention also provides the fluorescent aramid fiber prepared by the preparation method based on aggregation-induced emission, which comprises aramid fiber and fluorescent dye dispersed in the aramid fiber and having an aggregation-induced emission effect.
Further, the diameter of the fluorescent aramid fiber based on aggregation-induced emission is 15-100 μm.
The diameter of the obtained fluorescent aramid fiber based on aggregation-induced emission can be adjusted by changing the flow rate ratio of the inner phase solution to the outer phase solution, and the diameter of the fluorescent aramid fiber based on aggregation-induced emission is larger when the flow rate of the inner phase solution is increased while the flow rate of the outer phase solution is unchanged. In addition, the diameter of the fluorescent aramid fiber based on aggregation-induced emission is also affected by the inner diameter of the internal phase channel.
The invention also discloses application of the fluorescence aramid fiber based on aggregation-induced emission in information encryption and/or anti-counterfeiting.
By the scheme, the invention at least has the following advantages:
the invention provides a fluorescent aramid fiber based on aggregation-induced emission and a preparation method thereof, which solve the problems of low fluorescence intensity and easy quenching of the existing fluorescent fiber, have the advantages of simple process, mild conditions, safety and energy conservation, and the prepared fluorescent aramid fiber has high fluorescence efficiency, good stability and good fluorescence durability and has wide application prospect in the fields of information encryption and/or anti-counterfeiting.
The foregoing description is only an overview of the technical solutions of the present invention, and in order to make the technical solutions of the present invention more clearly understood and to implement them in accordance with the contents of the description, the following description is made with reference to the preferred embodiments of the present invention and the accompanying detailed drawings.
Drawings
FIG. 1 is a drawing showing the preparation of the title compound in example 11H NMR spectrum;
FIG. 2 is a fluorescence spectrum of the objective compound prepared in example 1 in a system of different volume ratios of tetrahydrofuran to water;
FIG. 3 is a schematic view of a microfluidic device according to example 2; FIG. 3b) is an enlarged view at the box of FIG. 3 a);
FIG. 4 is a scanning electron microscope image of the surface of the fluorescent aramid fiber prepared in example 2;
FIG. 5 is a cross-sectional scanning electron microscope image of the fluorescent aramid fiber prepared in example 2;
FIG. 6 is a fluorescence spectrum of the fluorescent aramid fiber prepared in example 2;
FIG. 7 is a photograph of the fluorescent aramid fiber prepared in example 2 under 365nm UV irradiation;
fig. 8 is a fluorescence spectrum of the fluorescent aramid fiber prepared in example 2 after being naturally left for 1 month, 3 months, and 6 months;
FIG. 9 is a scanning electron microscope image of the fluorescent aramid fiber prepared in example 2 at different external phase ratios;
fig. 10 is a graph showing the relationship between the diameter of the fluorescent aramid fiber prepared in example 2 and the flow rate of the internal and external phase solution.
Detailed Description
The following examples are given to further illustrate the embodiments of the present invention. The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
Example 1 Synthesis of aggregation-induced emission fluorescent dye
(1) Synthesis of Compound 1:
p-hydroxyphenylacetonitrile (5.8g, 44mmol), 3, 4-dihydro-2H-pyran (10mL, 48mmol) and pyridinium 4-methylbenzenesulfonate (100mg) were dissolved in 50mL of dichloromethane, stirred at room temperature for 24H and the progress of the reaction was checked by TLC. After the reaction, the reaction mixture was extracted 3 times with pure water, methylene chloride was dried by a rotary evaporator, 100mL of petroleum ether was added for recrystallization, and the mixture was filtered to obtain 10.2g (40.8mmol) of a white solid with a yield of 57%.
(2) Synthesis of Compound 2:
compound 1(3.36g, 15mmol), 1-naphthaldehyde (2.34g, 15mmol) and sodium hydroxide (210mg, 5.25mmol) were dissolved in 75mL of anhydrous ethanol, slowly warmed to 65 deg.C, stirred under reflux for 12h, and the progress of the reaction was checked by TLC. After completion of the reaction, the reaction solution was filtered and washed with absolute ethanol several times to obtain insoluble matter, which was then applied to silica gel and purified by a column chromatography (petroleum ether: ethyl acetate: 15:1, v/v) to obtain 4.05g (10.7mmol) of pale yellow solid in 71% yield.
(3) Synthesis of target compound:
compound 2(3.2g, 8.4mmol) was dissolved in 10mL tetrahydrofuran, 2 drops of concentrated HCl were added slowly dropwise, stirred at room temperature for 12h, and the progress of the reaction was checked by TLC. After completion of the reaction, the reaction mixture was purified by adding 250mL of pure water, and the reaction mixture was filtered to obtain insoluble matter, which was then applied to silica gel and purified by a column chromatography (petroleum ether: ethyl acetate: 5:1, v/v) to obtain 2.4g (8.5mmol) of a pale yellow solid with a yield of 75%.
The hydrogen spectrum data of the target compound prepared above are:1H NMR(400MHz,DMSO-d6)δ(ppm):9.16(s,1H),7.65(s,1H),7.29(s,1H),7.18(s,2H),7.08(s,1H) 6.89(s,2H),6.77(s,3H),6.07(s,2H) (as shown in FIG. 1).
The target compound prepared in example 1 was dissolved in tetrahydrofuran/water solutions of different volume ratios such that the molar concentration of the target compound in the solution was 10-5mol/L, and then detected by fluorescence spectrum F-4600 (Japan), the results are shown in FIG. 2.
Example 2 preparation of fluorescent aramid fibers based on aggregation-induced emission
(1) Preparing aramid spinning solution: weighing 0.04g of target compound powder prepared in example 1, dissolving the target compound powder in 10mL of DMAc solvent, adding 10mL of aramid fiber spinning stock solution (the aramid fiber spinning stock solution consists of aramid fiber and DMAc, wherein the concentration of the aramid fiber is 22%) after the target compound is fully dissolved, stirring the mixture on a magnetic stirrer at normal temperature for 3 hours, standing and defoaming the mixture for 2 hours to obtain the aramid fiber spinning solution with the target compound concentration of 0.2 wt%, and taking the aramid fiber spinning solution as an internal phase solution of microfluidic spinning.
(2) A solution with a DMAc and water ratio (v/v) of 70:30 was prepared as the external phase solution for microfluidic spinning.
(3) And (2) carrying out microfluidic spinning by using a microfluidic spinning device, wherein the microfluidic spinning device (shown in figure 3) consists of an outer phase channel and an inner phase channel coaxially arranged in the outer phase channel, the inner phase channel and the outer phase channel are both capillaries, the inner phase channel is a conical capillary, the inner diameter of the inner phase channel is 150 micrometers, and the inner diameter of the outer phase channel is 800 micrometers. The flow rate of the inner phase solution in the micro-fluidic spinning technology is controlled to be 5 mu L/min, and the flow rate of the outer phase solution is controlled to be 150 mu L/min. And the inner phase solution flows into the outer phase channel through the inner phase channel, is wrapped by the outer phase solution and then flows out of the outer phase channel, and different fluorescence aramid fibers based on aggregation-induced emission are obtained after solidification and drying.
The obtained fluorescent aramid fiber was placed on a copper stand, sprayed with gold, and then placed on a scanning electron microscope (S4800, japan) to observe the morphology. As shown in fig. 4-5, the fluorescent aramid fiber is solid and cylindrical, has a smooth and flat surface and a compact and uniform structure.
The fluorescence property of the fluorescent aramid fiber is detected by a fluorescence spectrometer F-4600 (Japan), and the result is shown in figure 6, which shows that the prepared fluorescent aramid fiber has a maximum emission peak at 449 nm.
The prepared fluorescent aramid fiber presents bright blue light under a 365nm ultraviolet lamp (as shown in figure 7), and can be used in the fields of information encryption and anti-counterfeiting by utilizing the performances. Fig. 8 is a fluorescence spectrum of the fluorescent aramid fiber prepared as described above after being naturally left for 1 month, 3 months, and 6 months. After natural standing for 6 months, the fluorescence effect of the fiber is still bright.
In addition, in order to investigate the influence of the ratio of the organic solvent and water in the external phase on the produced fluorescent fiber, solutions having a DMAc and water ratio (v/v) of 30:70, 40:60, 50:50, 60:40 and 70:30, respectively, were prepared as external phase solutions for microfluidic spinning, and microfluidic spinning was performed using the microfluidic spinning apparatus shown in fig. 3. As shown in FIG. 9, the sectional SEM images of the fibers obtained in FIG. 9, in which a-e correspond to the DMAc and water ratios (v/v) of 30:70, 40:60, 50:50, 60:40 and 70:30, respectively, and the surface SEM images of the fibers in FIGS. a-e correspond to FIGS. a1-e1, respectively. The results show that the internal structure of the fiber gradually changes from a porous structure to a solid compact structure with the increase of the DMAc content in the external phase solution.
In addition, in order to study the influence of the flow velocity of the internal and external phase solutions on the prepared fibers, different fibers were prepared by changing the flow velocity of the internal and external phase solutions. FIG. 10a) shows graphically the diameter results for fibers made with an external phase flow rate of 250. mu.L/min and an internal phase flow rate of 2.5, 5, 10, 15, 20. mu.L/min, FIG. 10b) shows graphically the diameter results for fibers made with an internal phase flow rate of 5. mu.L/min and an external phase flow rate of 50, 150, 250, 350, 450, 550. mu.L/min. The results show that the flow velocity of the external phase is constant, and the larger the flow velocity of the internal phase is, the larger the fiber diameter is; the flow rate of the inner phase is constant, and the larger the flow rate of the outer phase, the smaller the fiber diameter.
Example 3
A fluorescent aramid fiber based on aggregation-induced emission was prepared as in steps (1) to (3) of example 2, except that, in step (1), a fluorescent dye having an aggregation-induced emission effect was replaced with a compound of the following structural formula:
example 3
A fluorescent aramid fiber based on aggregation-induced emission was prepared as in steps (1) to (3) of example 2, except that, in step (1), a fluorescent dye having an aggregation-induced emission effect was replaced with a compound of the following structural formula:
the above is only a preferred embodiment of the present invention, and is not intended to limit the present invention, it should be noted that, for those skilled in the art, many modifications and variations can be made without departing from the technical principle of the present invention, and these modifications and variations should also be regarded as the protection scope of the present invention.
Claims (10)
1. A preparation method of a fluorescent aramid fiber based on aggregation-induced emission is characterized by comprising the following steps:
the method comprises the steps of adopting a micro-fluidic spinning method, taking an aramid spinning solution as an internal phase solution, wherein the aramid spinning solution comprises a fluorescent dye with an aggregation-induced emission effect and aramid, taking a mixed solution of an organic solvent and water as an external phase solution, and injecting the internal phase solution into the external phase solution to solidify the obtained fiber to obtain the fluorescence aramid fiber based on aggregation-induced emission.
2. The method of claim 1, wherein: the fluorescent dye with aggregation-induced emission effect comprises a compound with one or more of the following structural formulas:
3. the method of claim 1, wherein: in the aramid fiber spinning solution, the mass fraction of the fluorescent dye with aggregation-induced emission effect is 0.1-0.5%.
4. The method of claim 1, wherein: in the aramid spinning solution, the mass fraction of aramid fiber is 10-12%.
5. The method of claim 1, wherein: the solvent in the aramid spinning solution comprises one or more of N 'N-dimethylacetamide, N' N-dimethylformamide and dimethyl sulfoxide; the organic solvent in the external phase solution comprises one or more of N 'N-dimethylacetamide, N' N-dimethylformamide and dimethyl sulfoxide.
6. The method of claim 1, wherein: the volume ratio of the organic solvent to the water is 3-7: 3-7.
7. The method of claim 1, wherein: the microfluidic spinning method is carried out by adopting a microfluidic device, the microfluidic device comprises an inner phase channel for containing the inner phase solution and an outer phase channel for containing the outer phase solution, and the inner diameter ratio of the inner phase channel to the outer phase channel is 1-1.8: 6-8.
8. The method of claim 1, wherein: the flow rate of the inner phase solution is 2-20 mu L/min, and the flow rate of the outer phase solution is 50-550 mu L/min.
9. A fluorescent aramid fiber based on aggregation-induced emission prepared by the preparation method of any one of claims 1 to 8, characterized in that: the dye comprises aramid fiber and fluorescent dye with aggregation-induced emission effect dispersed in the aramid fiber.
10. Use of the aggregation-induced emission-based fluorescent aramid fiber of claim 9 for information encryption and/or anti-counterfeiting.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112961098A (en) * | 2021-02-09 | 2021-06-15 | 广东工业大学 | Organic fluorescent material containing pyrene unit and having aggregation induced luminescence, and preparation method and application thereof |
| CN113122947A (en) * | 2021-04-25 | 2021-07-16 | 江苏新视界先进功能纤维创新中心有限公司 | Multi-base color-changing luminescent fiber with antibacterial property and preparation method thereof |
| CN113307748A (en) * | 2021-04-27 | 2021-08-27 | 河北大学 | Broad-spectrum protein fluorescent probe and preparation method and application thereof |
| CN114395247A (en) * | 2022-01-28 | 2022-04-26 | 福州大学 | Polyamide 6 fluorescent composite material and preparation method thereof |
| CN114481678A (en) * | 2022-01-04 | 2022-05-13 | 煤炭科学研究总院有限公司 | Modified para-aramid nano-fiber and preparation method and application thereof |
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| CN110656387A (en) * | 2019-10-15 | 2020-01-07 | 中国科学院长春应用化学研究所 | Microfluidic biological spinning technology suitable for chemical crosslinking forming |
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| CN106381555A (en) * | 2016-08-26 | 2017-02-08 | 华南理工大学 | Composite fiber containing aggregation-induced luminescent molecules, preparation method thereof and application thereof |
| CN110512311A (en) * | 2019-09-09 | 2019-11-29 | 苏州大学 | A method of utilizing microflow control technique controllable preparation graphene fiber |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112961098A (en) * | 2021-02-09 | 2021-06-15 | 广东工业大学 | Organic fluorescent material containing pyrene unit and having aggregation induced luminescence, and preparation method and application thereof |
| CN112961098B (en) * | 2021-02-09 | 2023-01-20 | 广东工业大学 | Organic fluorescent material containing pyrene unit and having aggregation induced luminescence, and preparation method and application thereof |
| CN113122947A (en) * | 2021-04-25 | 2021-07-16 | 江苏新视界先进功能纤维创新中心有限公司 | Multi-base color-changing luminescent fiber with antibacterial property and preparation method thereof |
| CN113307748A (en) * | 2021-04-27 | 2021-08-27 | 河北大学 | Broad-spectrum protein fluorescent probe and preparation method and application thereof |
| CN113307748B (en) * | 2021-04-27 | 2022-06-28 | 河北大学 | Broad-spectrum protein fluorescent probe and preparation method and application thereof |
| CN114481678A (en) * | 2022-01-04 | 2022-05-13 | 煤炭科学研究总院有限公司 | Modified para-aramid nano-fiber and preparation method and application thereof |
| CN114395247A (en) * | 2022-01-28 | 2022-04-26 | 福州大学 | Polyamide 6 fluorescent composite material and preparation method thereof |
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