CN111468081A - Magnetic polymer microsphere, preparation method thereof and dye adsorbent - Google Patents
Magnetic polymer microsphere, preparation method thereof and dye adsorbent Download PDFInfo
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- CN111468081A CN111468081A CN202010290098.4A CN202010290098A CN111468081A CN 111468081 A CN111468081 A CN 111468081A CN 202010290098 A CN202010290098 A CN 202010290098A CN 111468081 A CN111468081 A CN 111468081A
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/261—Synthetic macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
- B01J20/06—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising oxides or hydroxides of metals not provided for in group B01J20/04
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28002—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their physical properties
- B01J20/28009—Magnetic properties
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28014—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their form
- B01J20/28016—Particle form
- B01J20/28021—Hollow particles, e.g. hollow spheres, microspheres or cenospheres
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/28—Treatment of water, waste water, or sewage by sorption
- C02F1/285—Treatment of water, waste water, or sewage by sorption using synthetic organic sorbents
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- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/40—Aspects relating to the composition of sorbent or filter aid materials
- B01J2220/48—Sorbents characterised by the starting material used for their preparation
- B01J2220/4806—Sorbents characterised by the starting material used for their preparation the starting material being of inorganic character
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- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/40—Aspects relating to the composition of sorbent or filter aid materials
- B01J2220/48—Sorbents characterised by the starting material used for their preparation
- B01J2220/4812—Sorbents characterised by the starting material used for their preparation the starting material being of organic character
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/30—Organic compounds
- C02F2101/308—Dyes; Colorants; Fluorescent agents
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Abstract
The application provides a magnetic polymer microsphere, which comprises a porous resin microsphere, magnetic particles dispersed in the porous resin microsphere and diazo resin adsorbed on the surface of the porous resin microsphere, wherein the porous resin microsphere and the diazo resin pass through-SO3-linked, the diazo resin having amino or imino groups.
Description
Technical Field
The application relates to the field of material preparation, in particular to a magnetic polymer microsphere, a preparation method thereof and a dye adsorbent.
Background
The Color Filter (CF) is a key component for realizing colorization of a liquid Crystal Display (L i quick Crystal Display, L CD). The working principle of the Color filter is that light rays of three primary colors of red (R), green (G) and blue (B) are generated by filtering a backlight, and then the light rays of the three primary colors are mixed in different proportions to obtain light rays of various colors, so that L CD shows colors, and the performances of the Color filter such as Color purity, brightness, contrast and the like can directly influence the performances such as Color saturation, Display brightness, contrast and the like of L CD.
Disclosure of Invention
In view of the above, the present application aims to provide a magnetic polymer microsphere capable of effectively removing a dye in wastewater, a preparation method thereof, and a dye adsorbent.
The application provides a magnetic polymer microsphere, which comprises a porous resin microsphere, magnetic particles dispersed in the porous resin microsphere and diazo resin adsorbed on the surface of the porous resin microsphere, wherein the porous resin microsphere and the diazo resin are connected through-SO 3-, and amino or imino is contained in the diazo resin.
In one embodiment, the content of amino or imino groups in the magnetic polymer microspheres ranges from 0.1mmol/g to 50 mmol/g.
In one embodiment, the surface of the magnetic polymer microsphere further comprises free sulfonic acid groups attached thereto.
In one embodiment, the free sulfonic acid group content ranges from 0.1mmol/g to 10 mmol/g.
In one embodiment, the diazo resin is a diazo resin represented by the following formula (1),
wherein Q is hydrogen or a substituent.
In one embodiment, the magnetic polymeric microspheres have a particle size in the range of 0.5um to 20 um.
The present application also provides a dye-adsorbent comprising magnetic polymeric microspheres as described in any one of the above.
The application also provides a preparation method of the magnetic polymer microsphere, which comprises the following steps:
providing tree porous resin microspheres, and sulfonating the porous resin microspheres to form sulfonic groups on the surfaces of the porous resin microspheres;
growing magnetic particles in the porous resin microspheres to obtain magnetic microspheres;
immersing the magnetic microspheres into a diazo resin solution containing acid to enable the magnetic microspheres to adsorb the diazo resin solution, wherein amino or imino is contained in the diazo resin;
and irradiating the magnetic microspheres adsorbed with the diazo resin solution by using ultraviolet light to obtain the magnetic polymer microspheres.
In one embodiment, the diazo resin is selected from one or more compounds represented by the following formula (2),
wherein Q is hydrogen or a substituent, and X-is an anion.
In one embodiment, in the step of immersing the magnetic microspheres in a diazo resin solution containing acid, the PH of the solution is adjusted to control the content of free sulfonic acid groups in the magnetic polymer microspheres.
The surface of the magnetic polymer microsphere provided by the application contains both free sulfonic acid groups (showing electronegativity in solution) and amino groups or imino groups (showing electropositivity in solution). The magnetic polymer microsphere can be used as a dye adsorbent to adsorb cationic dye and anionic dye at the same time. And the porous structure enables the dye adsorbent to have a large specific surface area and stronger adsorption performance.
Drawings
In order to more clearly illustrate the technical solutions in the present application, the drawings needed to be used in the description of the embodiments will be briefly introduced below, and it is obvious that the drawings in the following description are only some embodiments of the present application, and it is obvious for those skilled in the art to obtain other drawings based on these drawings without creative efforts.
FIG. 1 is a schematic representation of magnetic polymeric microspheres provided in a first embodiment of the present application.
Fig. 2 is a schematic diagram of a method for preparing magnetic polymer microspheres according to a second embodiment of the present disclosure.
FIG. 3 is a Fourier transform infrared spectrum of reactants and products of a process for preparing magnetic polymeric microspheres according to a second embodiment of the present disclosure.
Fig. 4 is a comparative graph of an experiment of adsorbing methylene blue dye by using magnetic polymer microspheres provided in the first embodiment of the present application.
Detailed Description
The technical solution in the present application will be clearly and completely described below with reference to the accompanying drawings in the embodiments of the present application. It should be apparent that the described embodiments are only some embodiments of the present application, and not all embodiments. All other embodiments, which can be obtained by a person skilled in the art without making any inventive step based on the embodiments in the present application, are within the scope of protection of the present application.
The dye adsorbent can be used for adsorbing pollutants in water, such as dye contained in wastewater generated in the filter manufacturing process of adsorbing L CD.
The dye adsorbents provided herein include magnetic polymer microspheres 100 as shown in fig. 1. The magnetic polymer microsphere 100 includes a porous resin microsphere, magnetic particles dispersed in the porous resin microsphere, and diazo resin R adsorbed on the surface of the porous resin microsphere. Porous resin microspheres and diazo resin R pass-SO3-linked, the diazo resin R has an amino group or an imino group. The surface of the magnetic polymer microsphere can also be connected with free sulfonic groups. The present application does not limit the material of the porous resin microspheres and the magnetic particles. In one embodiment, the material of the porous resin microspheres is selected from one or more of polyethylene terephthalate, polymethyl methacrylate, and polystyrene. The magnetic particles can be pure iron powder, carbonyl iron, ferroferric oxide, ferrate and the like.
In one embodiment, the magnetic polymeric microspheres have a particle size in the range of 0.5um to 20 um. In one embodiment, the content of free sulfonic acid groups in the magnetic polymer microspheres ranges from 0.1mmol/g to 10 mmol/g. The content range of amino or imino in the magnetic polymer microsphere is 0.1mmol/g to 50 mmol/g. Within this range, the adsorption performance is the best.
Since the surface of the magnetic polymer microsphere 100 contains both free sulfonic acid groups (exhibiting electronegativity in solution) and amino groups or imino groups (exhibiting electropositivity in solution). The magnetic polymer microsphere 100 as a dye adsorbent can adsorb cationic dyes and anionic dyes simultaneously. And the porous structure enables the dye adsorbent to have a large specific surface area and stronger adsorption performance.
In one embodiment, the magnetic polymer microspheres 100 may be SPS/Fe3O4a/DR microsphere. SPS refers to sulfonated polystyrene. DR refers to Diazoresin.
The diazo resin R is selected from one or more of diazo resins represented by the following formula (1),
wherein Q is hydrogen or a substituent.
The substituents may be selected from one or more of halogen, alkyl, alkoxy, hydroxy, aromatic, or the like.
The diazo resin has benzene rings on the chain, and pi-pi acting force is generated between the benzene rings. The dye adsorbent can also enhance the adsorption effect on the dye by utilizing pi-pi acting force.
In the manufacturing process of the display panel, the yellow light process of the color filter comprises the following steps: coating color resistance material, physical vapor deposition, prebaking, exposure, development, postbaking and the like. In the developing section, the developer dissolves the uncured color-resisting material, and the dissolved waste water carries the dye. When the dye adsorbent provided by the application is dissolved in water, a positively charged group (diazo group) and a negatively charged group (sulfonic group) are generated on the surface, and a cationic dye and an anionic dye in water can be adsorbed simultaneously. Place the dyestuff adsorbent that this application provided in the filter of development section or in the waste water treatment pond, can reach the purpose of water purification. Because the adsorbent contains magnetic particles, the adsorbent can be quickly collected and treated after wastewater treatment is finished, and time cost is reduced. The dye adsorbent provided by the invention has the advantages of simple preparation, good adsorption effect, low cost and the like.
Referring to fig. 2, the present application further provides a method for preparing a magnetic polymer microsphere 100, which comprises the following steps:
s1: providing porous resin microspheres, and sulfonating the porous resin microspheres to form sulfonic groups on the surfaces of the porous resin microspheres.
The material of the porous resin microspheres is selected from one or more of polyethylene terephthalate, polymethyl methacrylate and polystyrene. In this step, the resin microspheres may be immersed in concentrated sulfuric acid and heated to react, thereby sulfonating the porous resin microspheres to form sulfonic acid groups on the surfaces of the porous resin microspheres. The sulfonation reaction conditions, such as temperature and reaction time, can be referred to the prior art and are not described in detail herein.
S2: and growing magnetic particles in the porous resin microspheres to obtain the magnetic microspheres.
The magnetic particles can be pure iron powder, carbonyl iron, ferroferric oxide, ferrate and the like.
In one embodiment, the magnetic particles may be ferroferric oxide. The method of growing the magnetic particles may be: immersing porous resin microspheres in a solution containing iron ions (Fe)3+) And/or ferrous ions (Fe)2+) In the salt solution, iron ions and/or ferrous ions and-SO on the surface of the porous resin microspheres3The H sulfonate is adsorbed by electrostatic binding. Then washing the porous resin microspheres, transferring the porous resin microspheres into an ammonia water solution, and obtaining Fe3O4The particles can grow inside the pores of the SPS.
S3: and (3) immersing the magnetic microspheres into a diazo resin solution containing acid to enable the magnetic microspheres to adsorb the diazo resin solution. The diazo resin has an amino group or an imino group. By regulating the acid contentThe pH value of the diazoresin solution can control the content of free sulfonic groups in the product. The acid may be H2SO4。
In one embodiment, the diazo resin is a diazo resin represented by the following formula (2),
wherein Q is hydrogen or a substituent, X-Is an anion.
The substituents may be selected from one or more of halogen, alkyl, alkoxy, hydroxy, aromatic, or the like.
In this step, the part of the surface of the magnetic microspheres-SO3NH4The radicals being converted into free-SO by the action of acids3H, preparation of-N of diazo resin2+with-SO on the surface of the magnetic microspheres3-bonding by electrostatic forces.
S4: and irradiating the magnetic microspheres adsorbed with the diazo resin solution by using ultraviolet light to obtain the magnetic polymer microspheres.
Diazo resin is a photosensitive material, and diazo groups contained in the diazo resin become free radicals or positive ions under the irradiation of ultraviolet light, and are subjected to photo-cracking, so that covalent bonds are formed between the diazo resin and the magnetic microspheres, and the resin is firmly bonded on the microspheres.
In one embodiment, the magnetic polymeric microspheres have a particle size in the range of 0.5um to 20 um.
Referring now to fig. 2, a method for preparing magnetic polymeric microspheres 100 according to one embodiment of the present disclosure is illustrated.
First, 98% H was added to porous polystyrene microspheres2SO4The solution is heated to 120 ℃ for 12 hours after being evenly stirred until the porous polystyrene microspheres are submerged; cooling to room temperature, adding into ice water mixture for crystallization, centrifuging, and cleaning for later use.
Next, 200mg of sulfonated porous polystyrene microspheres were added to a solution containing 0.043g FeCl2·4H2O and 0.118g FeCl3·6H2O in 20m L aqueous solutionIn the middle, the mixture is evenly mixed to ensure-SO3Better adsorption of Fe2+And Fe3+Cleaning, then adding 2.5m L NH under nitrogen atmosphere3·H2O, reacting at 80 ℃ for 30min to obtain sulfonated polystyrene/Fe3O4And (5) cleaning and drying the microspheres for later use. In this step, sulfonated polystyrene particles are soaked in FeCl2/FeCl3In the mixed solution of (1), Fe2+And Fe3+Ions and-SO3H (sulfonate) is combined through electrostatic action to adsorb two ions. Then washing the microsphere particles, transferring into ammonia water solution, and Fe3O4The particles can grow inside the pores of the SPS. In this step, the sulfonated porous polystyrene microspheres have sulfuric acid in themselves, thus promoting Fe2+And Fe3+Ions and-SO3H (sulfonate) is bound by electrostatic interaction. In addition, acid can be added to adjust the pH value to adjust the free-SO3The concentration of H.
Then, the sulfonated polystyrene/Fe3O4Soaking the microspheres in 50 mg/L diazo resin solution for 30min, cleaning, separating, and repeating the soaking-cleaning operation for several times to ensure the adsorption of the diazo resin.
And finally, irradiating the microspheres for 1h by 365nm ultraviolet light to enable diazo resin and the microspheres to form covalent bonds, thereby obtaining the stable magnetic polymer microspheres 100.
During the preparation, the reactants and products were characterized by Fourier transform Infrared Spectroscopy (FT-IR), and the obtained FT-IR spectrum is shown in FIG. 3. Wherein, a represents the FT-IR spectrum of solid polystyrene microspheres (PS) used as a reference; b represents the FT-IR spectrum of porous polystyrene microspheres (SPS); c represents magnetic microspheres (SPS/Fe)3O4) (ii) a FT-IR spectrum of (A); d represents magnetic polymer microspheres (SPS/Fe)3O4/DR).
Wherein the content of the first and second substances,
2924cm-1and 2850cm-1Is represented by-CH2-stretching vibrations;
1640cm-1and 1450cm-1Represented is vibration of aromatic benzene ring;
1175cm-1and 1038cm-1Representative is stretching vibration of-S ═ O bond;
3424cm-1represented is the vibration of the O-H bond;
580cm-1represented by vibration of Fe-O bond;
1380cm-1representative is vibration of C-N bond
The above data may illustrate SPS/Fe3O4the/DR was successfully prepared.
SPS/Fe prepared in example3O4FIG. 4 shows the comparison between the adsorption experiment of/DR on Methylene Blue (MB) dye and the comparison between the adsorption experiment and the experiment, and it can be seen that SPS/Fe prepared in the present application3O4the/DR has good adsorption effect on the cationic dye. In addition, SPS/Fe prepared in the examples3O4The adsorption experiment of azo dyes by using/DR is similar to that of FIG. 4, and better adsorption results are obtained, so that SPS/Fe prepared in the application can be known3O4the/DR also has good adsorption effect on anionic dyes.
Compared with the prior art, the preparation method of the magnetic polymer microsphere has the advantages of simple preparation and low cost.
The foregoing provides a detailed description of embodiments of the present application, and the principles and embodiments of the present application have been described herein using specific examples, which are presented solely to aid in the understanding of the present application. Meanwhile, for those skilled in the art, according to the idea of the present application, there may be variations in the specific embodiments and the application scope, and in summary, the content of the present specification should not be construed as a limitation to the present application.
Claims (10)
1. The magnetic polymer microsphere is characterized by comprising a porous resin microsphere, magnetic particles dispersed in the porous resin microsphere and diazo adsorbed on the surface of the porous resin microsphereResin, the porous resin microspheres and the diazo resin pass through-SO3-linked, the diazo resin having amino or imino groups.
2. The magnetic polymeric microspheres of claim 1, wherein the content of amino or imino groups in the magnetic polymeric microspheres ranges from 0.1mmol/g to 50 mmol/g.
3. The magnetic polymeric microsphere of claim 1, wherein the surface of the magnetic polymeric microsphere further comprises free sulfonic acid groups attached thereto.
4. The magnetic polymer microspheres of claim 3, wherein the free sulfonic acid group content ranges from 0.1mmol/g to 10 mmol/g.
5. The magnetic polymer microsphere of claim 1, wherein the diazo resin is a diazo resin represented by the following formula (1),
wherein Q is hydrogen or a substituent.
6. The magnetic polymeric microspheres of claim 1, wherein the magnetic polymeric microspheres have a particle size in the range of 0.5um to 20 um.
7. A dye-adsorbing agent comprising the magnetic polymer microsphere according to any one of claims 1 to 6.
8. A preparation method of magnetic polymer microspheres comprises the following steps:
providing tree porous resin microspheres, and sulfonating the porous resin microspheres to form sulfonic groups on the surfaces of the porous resin microspheres;
growing magnetic particles in the porous resin microspheres to obtain magnetic microspheres;
immersing the magnetic microspheres into a diazo resin solution containing acid to enable the magnetic microspheres to adsorb the diazo resin solution, wherein amino or imino is contained in the diazo resin;
and irradiating the magnetic microspheres adsorbed with the diazo resin solution by using ultraviolet light to obtain the magnetic polymer microspheres.
9. The method for preparing magnetic polymer microspheres according to claim 8, wherein the diazo resin is one or more selected from the group consisting of compounds represented by the following formula (2),
wherein Q is hydrogen or a substituent, and X-is an anion.
10. The method for preparing magnetic polymer microspheres according to claim 8, wherein in the step of immersing the magnetic microspheres in a diazo resin solution containing an acid, the PH of the solution is adjusted to control the content of free sulfonic acid groups in the magnetic polymer microspheres.
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| CN114854085A (en) * | 2022-04-20 | 2022-08-05 | 中国科学院苏州生物医学工程技术研究所 | Photosensitive diazoresin coated magnetic porous microsphere and preparation method of fluorescence encoding magnetic microsphere |
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| CN1699447A (en) * | 2005-04-07 | 2005-11-23 | 天津大学 | Nano solid magnetic ion exchange resin ball and method for preparing same |
| US20100129794A1 (en) * | 2005-12-09 | 2010-05-27 | Roland Fabis | Magnetic Polymer Particles |
| CN103627022A (en) * | 2013-11-06 | 2014-03-12 | 江苏大学 | Method for preparing magnetic porous polystyrene microspheres on basis of suspension polymerization |
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2020
- 2020-04-14 CN CN202010290098.4A patent/CN111468081A/en not_active Withdrawn
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| CN1699447A (en) * | 2005-04-07 | 2005-11-23 | 天津大学 | Nano solid magnetic ion exchange resin ball and method for preparing same |
| US20100129794A1 (en) * | 2005-12-09 | 2010-05-27 | Roland Fabis | Magnetic Polymer Particles |
| CN103627022A (en) * | 2013-11-06 | 2014-03-12 | 江苏大学 | Method for preparing magnetic porous polystyrene microspheres on basis of suspension polymerization |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114854085A (en) * | 2022-04-20 | 2022-08-05 | 中国科学院苏州生物医学工程技术研究所 | Photosensitive diazoresin coated magnetic porous microsphere and preparation method of fluorescence encoding magnetic microsphere |
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Application publication date: 20200731 |