CN114395247A - Polyamide 6 fluorescent composite material and preparation method thereof - Google Patents
Polyamide 6 fluorescent composite material and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a polyamide 6 fluorescent composite material and a preparation method thereof. Polyamide 6 is a polymer material widely used in the fields of plastics, textiles, films and the like. According to the invention, the salicylaldehyde hydrazone compound is blended with polyamide 6, and the binary system has good dispersibility, can form a homogeneous material in wet spin coating film preparation and melt blending injection molding, and has remarkable photoluminescence property and good chemical stability. The preparation method is simple and feasible, the raw material price is moderate, and the production cost is low.
Description
Technical Field
The invention belongs to a polyamide material with fluorescent property, and particularly relates to a fluorescent material prepared by spin coating and melt blending a binary system containing salicylaldehyde hydrazone and polyamide 6 by a wet method.
Background
Polyamide is a polymer having an amide group as a repeating unit for polymerization. Because of the characteristics of good mechanical property, heat resistance, abrasion resistance, easy processing and the likeThe method develops materials such as plates, bars, fibers, films and the like, and is widely applied to various links of production and life. Wherein the polyamide 6 (hereinafter referred to as PA 6) is prepared by ring-opening polymerization of caprolactam and has a structural formula of [ -HN (CH)2)5CO-]n。
From the molecular structure, PA6 does not have a strong light-emitting ability. Although weak fluorescence can be observed by adjusting the state of molecular aggregation, it cannot be applied to a practical melt extrusion production process. Therefore, in order to obtain luminescent PA6 materials, it is a common strategy to add chromophores to prepare composite PA6 luminescent polymers in a grafting or copolymerization manner. However, this strategy is limited in production cost and product reproducibility by copolymerization or grafting reactions. On the other hand, it is also common practice to obtain luminescent composites by blending modification. The blending modification of PA6 refers to the physical blending of PA6 and fluorescent nanoparticles or molecules, generally does not generate the generation or the breakage of covalent bonds, and has the characteristics of simple and convenient operation and mild reaction conditions. However, since a strong chemical bond does not exist between the fluorescent molecule and PA6, the blended material often has a phase separation phenomenon, resulting in poor uniformity and reproducibility of the luminescence of the material. The high temperature treatment method of melt extrusion can solve the phase separation problem well, but requires the blended materials to have similar melting points, thus greatly limiting the types of the selectable fluorescent materials. On the other hand, a melt extrusion manufacturing process is generally adopted in actual production practice of PA6, so that a proper fluorescent blending material is selected, the fluorescent blending material is suitable for a melt extrusion manufacturing link, and the fluorescent property with good reproducibility can be embodied as a problem to be considered in the blending method research. Therefore, there is a need to further find suitable blending formulations.
In this context, the present invention blends a luminescent acylhydrazone compound with PA 6. The luminous acylhydrazone compound has AIE property and melting point similar to PA 6. In addition, the acylhydrazone functional group can form a relatively stable hydrogen bond with an amido bond of PA6, and the phase separation condition can be improved well. The luminescent acylhydrazone compound has 6 sites per molecule available for coordination or hydrogen bonding, possibly with the amide bond of PA 6. The prepared binary system can be used for preparing a film by wet spin coating at normal temperature, and can also be subjected to high-temperature heat treatment for melt extrusion and injection molding. The fluorescent composite polyamide material can be prepared by both methods.
Disclosure of Invention
The invention aims to obtain a composite polyamide 6 fluorescent material by a blending method and provides a preparation method thereof. According to the invention, an acylhydrazone fluorescent molecule is blended with PA6 to prepare a binary system which can be used for preparing a film by spin coating at normal temperature by a wet method, and can also be used for high-temperature melt extrusion injection molding, and the obtained film or plastic part has obvious photoluminescence properties, and also has high melting point and the capability of keeping stability in an acidic solution. The invention has the advantages of cheap and easily obtained raw materials, simple method and quick preparation process.
In order to achieve the purpose, the invention adopts the following technical scheme:
a preparation method of a polyamide 6 fluorescent composite material comprises the following steps:
1. preparation of 4, 4' -Diphenyleneformyl salicylaldehyde hydrazone (hereinafter referred to as L)
The preparation method of L comprises the following specific steps: adding salicylaldehyde and hydrazine hydrate into an absolute ethyl alcohol solvent, stirring the mixture at room temperature in an open manner, and separating out the salicylaldehyde hydrazone after the ethyl alcohol is volatilized; 4,4 '-diphenylethylene dicarboxylic acid and thionyl chloride are subjected to acyl chlorination reaction by taking a small amount of DMF as a catalyst to obtain 4, 4' -diphenylethylene diacid chloride; and finally, heating and refluxing the salicylaldehyde hydrazone and the 4, 4' -diphenylethylene dichloride with triethylamine as a catalyst and DMF as a solvent to react, removing the solvent, and washing the precipitate with absolute ethyl alcohol to obtain yellow powder, namely the product L. The yield was about 81.4%.
2. And (3) wet spin coating film preparation of a binary system of L and PA 6:
weighing L powder and PA6 powder (the mass ratio of L to PA6 is 1-8: 100) according to a certain proportion, dissolving the L powder and the PA6 powder in 98wt% formic acid solution, and stirring for 4 hours until the L powder and the PA6 are completely dissolved. And then flatly spreading the mixed solution on a spin coater, standing for 2min, then spin-coating, firstly rotating at a low speed (the rotating speed is 500r/min and 30 s), and then rotating at a high speed (3000 r/min and 30 s). The blend film of L and PA6 was obtained and left at room temperature without further treatment.
3. Melt extrusion injection molding of the binary system of L and PA 6:
drying the L powder and the PA6 powder in an oven at 80 ℃ overnight, blending and stirring the powder (the mass ratio of L to PA6 is 0.1-2: 100), carrying out melt blending on the mixed powder by using a double-screw extruder, heating an upper plate and a lower plate to 230 ℃, keeping the screw rotation speed at 70r/min, feeding the mixture at 10g/min, introducing nitrogen, carrying out self-circulation stirring for 2min, and then carrying out extrusion cooling by using an injection molding machine to obtain a dumbbell shape. The mold temperature of the injection molding machine was 50 ℃.
The invention has the following remarkable advantages:
according to the invention, the salicylaldehyde hydrazone compound is blended with polyamide 6, and the binary system has good dispersibility, can form a homogeneous material in wet spin coating film preparation and melt blending injection molding, and has remarkable photoluminescence property and good chemical stability. The preparation method is simple and feasible, the raw material price is moderate, and the production cost is low. The product has stronger fluorescence, better fluorescence stability in wider acid-base aqueous solution and different organic solvents, and better use value in practical application.
Drawings
FIG. 1 shows the nuclear magnetic hydrogen spectrum of ligand L (deuterated DMSO as solvent);
FIG. 2 is a fluorescence spectrum of ligand L and a spin-on film of PA 6;
FIG. 3 is a fluorescence spectrum of a melt-extruded injection-molded part of ligand L and PA 6.
Detailed Description
The present invention is further illustrated by the following examples, but the scope of the present invention is not limited to the following examples.
Example 1 (preparation L)
Synthesis of salicylaldehyde hydrazone: mixing 9 mL of salicylaldehyde and 8 mL of hydrazine hydrate with 10mL of absolute ethanol respectively, and dropwise adding the ethanol solution of the salicylaldehyde into the ethanol solution of the hydrazine hydrate; stirring the mixture at room temperature overnight in an open manner, and gradually precipitating white powder along with the volatilization of ethanol; filtering, and washing with ethanol to obtain the salicylaldehyde hydrazone.
Synthesis of 4, 4' -distyryl dichloride: weighing 10 mmol of 4, 4' -diphenylethylene diCarboxylic acid in round bottom flask, 20 mL SOCl2And 40. mu.L of DMF was added to the mixture, which was refluxed at 75 ℃ for 9 hours in a drying tube, and unreacted SOCl was removed by rotary evaporation2Obtaining yellow green acyl chloride powder which is 4, 4' -diphenylethylene diacyl chloride;
synthesis of fluorescent small molecule L: weighing 24 mmol of salicylaldehyde hydrazone, adding 10mL of DMF and 1.4 mL of triethylamine to dissolve the salicylaldehyde hydrazone in a round-bottom flask, adding 10 mmol of 4, 4' -diphenylethylene dichloride, and after mixing, moving the mixture to a 90 ℃ oil bath for reflux reaction for 9 hours; distilling off DMF under reduced pressure, cooling, and washing the residue with anhydrous ethanol; and then dissolving the mixture in DMSO to prepare a saturated solution, standing the saturated solution at room temperature overnight in an open manner, filtering the precipitated precipitate, and washing the precipitate with absolute ethyl alcohol to obtain yellow powder, namely the final product of 4, 4' -stilbene formyl salicylaldehyde hydrazone L. The yield was about 81.4%.
Example 2 (Wet spin-on film formation of binary System L and PA 6)
Weighing 0.01g L powder, adding into 10g of 98wt% formic acid solution, adding magnet, and stirring for 4h to dissolve completely; weighing 1g of PA6 powder, adding the PA6 powder into 9g of 98wt% formic acid solution, adding a magnet, stirring for 4 hours until the PA6 powder is completely dissolved, adding the L formic acid solution into the PA6 formic acid solution, and blending for 4 hours to obtain an L/PA6 formic acid solution with the L accounting for 1% of PA6 by mass, wherein the concentration of PA6 is 5 wt%. And (3) using a spin coating spin coater, taking a cover glass as a base, dripping 200uL of the blending solution until the cover glass is completely covered, standing for 2min, then spin-coating, firstly rotating at a low speed (the rotating speed is 500r/min and 30 s), and then rotating at a high speed (3000 r/min and 30 s). A film of L blended with PA6 (corresponding to the 1% curve in FIG. 2) was obtained, which was left at ambient temperature without further treatment.
The above L powder amounts were replaced with 0.02g, 0.04g, 0.07g, and 0.08g, respectively, and the remaining operating conditions were unchanged, to obtain 2%, 4%, 7%, and 8% L12/PA 6 blend films, respectively.
Example 3 (melt extrusion injection of a binary System L and PA 6)
The L powder and PA6 powder were placed in an oven at 80 ℃ and dried overnight to ensure accurate weighing. 0.1g of powder was weighed into 10gPA6 (corresponding to L12: PA6=1% in FIG. 3), and homogenized for 2min with a glass rod. And (3) carrying out melt extrusion on the blended powder by using a double-screw extruder, adjusting the rotating speed of the screw to 70r/min and the feeding speed to 10g/min after the temperatures of an upper plate and a lower plate of the double-screw extruder are stabilized to 230 ℃, carrying out self-circulation on the blended material in the extruder for 2min, and introducing nitrogen in the whole process. And transferring the material to an injection molding machine, and extruding and rapidly cooling to obtain the dumbbell-shaped material. The temperature of the injection molding machine mold is constant at 50 ℃.
The above L powder amounts were replaced with 0.01g, 0.02g, 0.05g, and 0.2g, respectively, and the remaining operating conditions were unchanged, to obtain 0.1%, 0.2%, 0.5%, and 2% of L12/PA 6 blended frits, respectively.
And (3) functional characterization of a product:
(1) nuclear magnetic hydrogen spectrum of compound L: in DMSO-d6Hydrogen nuclear magnetic characterization of L in the reagent (see fig. 1) was performed, and the groups of peaks were assigned as follows: 12.13 ppm of a proton peak attributed to H on acylhydrazone amine group, 11.31 ppm of a proton peak attributed to H on phenolic hydroxyl group, 8.67 ppm of a proton peak attributed to H on Schiff base methylene group, and 8.01-6.92 ppm of a proton peak attributed to H on benzene ring and vinyl group.
(2) Fluorescence properties of the blended films:
the prepared blend film was tested for fluorescence spectrum (see fig. 2). The films produced had a thickness of about 2-10um, indicating that the blend film had very little mass of PA6 and less L. In the fluorescence test, the mixed film is excited by light with the wavelength of 350nm, and the mixed film has the strongest fluorescence when the addition amount reaches 8 percent, and the maximum emission wavelength is 500 nm. When the addition amount is less than 4%, the maximum emission wavelength is 390nm, which is the fluorescence of the PA6 film, when the addition amount of L is in the range of 1% -4%, the PA6 luminescence in the blending material can be enhanced, when the addition amount of L is in the range of 4% -8%, the blending film mainly shows the fluorescence property of L because L is an AIE molecule. The L has better dispersibility in the film, and is aggregated when the content is more than 4 percent, so that the phenomenon of fluorescence enhancement shows that the improvement of the fluorescence property is mainly due to the addition of the L and the fluorescence property of the L in the blended film plays a main role. Therefore, when preparing L/PA6 film, it is preferable to add 4% of L.
(3) Fluorescence enhancement of the blended frit:
the prepared blended frit added in an amount of 0.1% to 2% was tested for fluorescence spectrum (see fig. 3). The frit was prepared to a thickness of 2 mm. Unlike the thin film properties, the frit has a better fluorescence intensity under 405nm excitation. When excited at 405nm, the frit was found to have the strongest fluorescence intensity when added at 1%. The fluorescence intensity of the frit was also increased when the amount was increased from 0.1%, and it was found that the fluorescence intensity was slightly decreased when the amount was more than 1%, indicating that the fluorescence intensity of the blended frit reached the maximum value. In the fluorescence of the frit, the maximum emission wavelength of the blended frit is mainly due to the fluorescence property exhibited by L after excitation, even in a small amount. It is shown that L is well dispersed in PA6 in the molten state, and the aggregation of L is related to the amount of the added material, so that the fluorescence intensity of the blended material is enhanced along with the increase of the added material. The quantum yield of the frit of PA6 is tested, the quantum yield of the frit of PA6 is 0.013, the quantum yield of 1% of the blended frit reaches 0.034, and the blending frit realizes the enhancement of the fluorescence property of PA6, and the feeding amount is 1% as the best.
The above description is only a preferred embodiment of the present invention, and all equivalent changes and modifications made in accordance with the claims of the present invention should be covered by the present invention.
Claims (7)
1. The preparation method of the polyamide 6 fluorescent composite material is characterized in that 4, 4' -stilbene formyl salicylaldehyde hydrazone and polyamide 6 are blended, and the polyamide 6 fluorescent composite material is obtained through wet spin coating film making or melt blending injection molding.
2. The method according to claim 1, wherein the method for preparing 4, 4' -stilbene formyl salicylaldohydrazone comprises the following steps:
(1) dissolving salicylaldehyde and hydrazine hydrate in an absolute ethyl alcohol solvent, stirring the mixture at room temperature in an open manner, and separating out the salicylaldehyde hydrazone after the ethyl alcohol is volatilized;
(2) mixing 4,4 '-diphenylethylene dicarboxylic acid and thionyl chloride, and carrying out acyl chlorination reaction by using DMF as a catalyst to obtain 4, 4' -diphenylethylene diacid chloride;
(3) mixing salicylaldehyde hydrazone with 4,4 '-stilbene-diacyl chloride, taking triethylamine as a catalyst and DMF as a solvent, heating and refluxing the mixture to react, removing the solvent, and washing precipitates with absolute ethyl alcohol to obtain yellow powdery 4, 4' -stilbene-formyl salicylaldehyde hydrazone.
3. The preparation method according to claim 1, wherein the method for preparing the polyamide 6 fluorescent composite material by wet spin-on film preparation comprises the following steps:
dissolving 4,4 '-stilbene formyl salicylaldehyde hydrazone powder and PA6 powder in 98wt% formic acid solution, stirring for 4h until the stilbene formyl salicylaldehyde hydrazone powder and the PA6 powder are completely dissolved, spreading the mixed solution on a spin coater, standing for 2min, then spin-coating, firstly rotating at a low speed for 30s and a rotating speed of 500r/min, then rotating at a high speed for 30s and a rotating speed of 3000r/min, and obtaining the blend film of the 4, 4' -stilbene formyl salicylaldehyde hydrazone and the PA6, namely the polyamide 6 fluorescent composite material.
4. The preparation method according to claim 3, wherein the mass ratio of the 4, 4' -distyrylbenzoyl salicylaldohydrazone powder to the PA6 powder is 1-8: 100.
5. The preparation method according to claim 1, wherein the method for preparing the polyamide 6 fluorescent composite material by melt blending injection molding comprises the following steps:
drying 4, 4' -stilbene formyl salicylaldehyde hydrazone powder and PA6 powder in an oven at the temperature of 80 ℃ overnight, then blending and stirring, carrying out melt blending on the mixed powder by using a double-screw extruder at the temperature of 230 ℃, keeping the screw rotation speed of 70r/min, the feeding speed of 10g/min, introducing nitrogen, carrying out self-circulation stirring for 2min, then extruding and cooling by using an injection molding machine to obtain the dumbbell-shaped polyamide 6 fluorescent composite material, wherein the mold temperature of the injection molding machine is 50 ℃.
6. The method according to claim 5, wherein the mass ratio of the 4, 4' -distyrylbenzoyl salicylaldohydrazone powder to the PA6 powder is 0.1-2: 100.
7. The polyamide 6 fluorescent composite material prepared by the preparation method according to any one of claims 1 to 6.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2015041729A2 (en) * | 2013-06-03 | 2015-03-26 | The Research Foundation Of State University Of New York | SITE-SPECIFIC ORTHOGONAL LABELING OF THE CARBOXY TERMINUS OF α-TUBULIN IN LIVE CELLS |
| CN110423346A (en) * | 2019-08-31 | 2019-11-08 | 湘潭大学 | A kind of polyamide liquid crystal macromolecule and preparation method thereof with aggregation-induced emission property |
| CN110849856A (en) * | 2019-12-03 | 2020-02-28 | 浙江大学 | Application of salicylaldehyde hydrazone derivative with aggregation-induced emission performance in detection of nitrite ions |
| CN111206288A (en) * | 2020-01-17 | 2020-05-29 | 苏州大学 | Fluorescent aramid fiber based on aggregation-induced emission and preparation and application thereof |
| CN113754560A (en) * | 2020-06-02 | 2021-12-07 | 东北林业大学 | Preparation method of salicylaldehyde-based fluorescent compound |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015041729A2 (en) * | 2013-06-03 | 2015-03-26 | The Research Foundation Of State University Of New York | SITE-SPECIFIC ORTHOGONAL LABELING OF THE CARBOXY TERMINUS OF α-TUBULIN IN LIVE CELLS |
| CN110423346A (en) * | 2019-08-31 | 2019-11-08 | 湘潭大学 | A kind of polyamide liquid crystal macromolecule and preparation method thereof with aggregation-induced emission property |
| CN110849856A (en) * | 2019-12-03 | 2020-02-28 | 浙江大学 | Application of salicylaldehyde hydrazone derivative with aggregation-induced emission performance in detection of nitrite ions |
| CN111206288A (en) * | 2020-01-17 | 2020-05-29 | 苏州大学 | Fluorescent aramid fiber based on aggregation-induced emission and preparation and application thereof |
| CN113754560A (en) * | 2020-06-02 | 2021-12-07 | 东北林业大学 | Preparation method of salicylaldehyde-based fluorescent compound |
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