CN113881043A - Polyhydroxy polymer microsphere and preparation method and application thereof - Google Patents
Polyhydroxy polymer microsphere and preparation method and application thereof Download PDFInfo
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- 239000004005 microsphere Substances 0.000 title claims abstract description 53
- 229920000642 polymer Polymers 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 15
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 claims abstract description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 10
- 238000001179 sorption measurement Methods 0.000 claims abstract description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims description 9
- 150000007530 organic bases Chemical class 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- 239000002244 precipitate Substances 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 4
- 238000004090 dissolution Methods 0.000 abstract 1
- 238000012673 precipitation polymerization Methods 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 230000006872 improvement Effects 0.000 description 7
- 239000000975 dye Substances 0.000 description 6
- 230000007547 defect Effects 0.000 description 5
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000011031 large-scale manufacturing process Methods 0.000 description 4
- 229960000907 methylthioninium chloride Drugs 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000007720 emulsion polymerization reaction Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001045 blue dye Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000012674 dispersion polymerization Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- MCPLVIGCWWTHFH-UHFFFAOYSA-L methyl blue Chemical compound [Na+].[Na+].C1=CC(S(=O)(=O)[O-])=CC=C1NC1=CC=C(C(=C2C=CC(C=C2)=[NH+]C=2C=CC(=CC=2)S([O-])(=O)=O)C=2C=CC(NC=3C=CC(=CC=3)S([O-])(=O)=O)=CC=2)C=C1 MCPLVIGCWWTHFH-UHFFFAOYSA-L 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 239000003774 sulfhydryl reagent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000635 electron micrograph Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- CSJDCSCTVDEHRN-UHFFFAOYSA-N methane;molecular oxygen Chemical compound C.O=O CSJDCSCTVDEHRN-UHFFFAOYSA-N 0.000 description 1
- 238000012701 michael addition polymerization Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001878 scanning electron micrograph Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
- C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated compounds
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/06—Making microcapsules or microballoons by phase separation
- B01J13/14—Polymerisation; cross-linking
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- 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
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Abstract
The invention discloses a polyhydroxy polymer microsphere and a preparation method thereof, wherein the preparation method comprises the following steps: dissolving acrylate and dithiothreitol in methanol, adding the mixture into triethylamine after complete dissolution, and standing for a period of time at room temperature to obtain the polymer microspheres with uniform size. The method has the advantages of common and easily obtained reagents and raw materials, high reaction rate, mild reaction conditions, simple operation method and wide application prospect in the field of adsorption.
Description
Technical Field
The invention belongs to the field of polymer synthesis, and particularly relates to a polyhydroxy polymer microsphere and a preparation method thereof.
Background
The polymer microsphere has the advantages of high specific surface area, controllable size, easy functionalization, high adsorption capacity and the like, and is widely applied to the fields of ion adsorption, dye adsorption, drug release, biomedicine, catalyst carriers and the like. Generally, polymeric microspheres can be prepared by microfluidics, suspension polymerization, dispersion polymerization, precipitation polymerization, and the like. The microfluidic method is a new polymer microsphere preparation technology, has advantages in controlling the composition, morphology and particle size of the polymer microsphere, but has the defect of difficult large-scale preparation; the suspension polymerization method has low cost, easy operation and easy large-scale production, but the prepared polymer microsphere has the defect of wide particle size distribution; the polymer microspheres prepared by emulsion polymerization have the characteristics of high molecular weight and good monodispersity, but the emulsifier in an emulsion polymerization product system is not easy to remove and easily affects the performance of the product, so that the application of the product is limited, and soap-free emulsion polymerization has no emulsifier residue, but the polymerization process has the defects of poor emulsion stability, low solid content and incapability of large-scale production; the dispersion polymerization has the advantages of simple, convenient and rapid preparation of monodisperse, functionalized and morphology-controllable polymer microspheres in a large scale, but the method can only prepare the polymer microspheres with the size of 500nm-10 mu m and cannot be used for preparing porous polymer microspheres; the precipitation polymerization is a main preparation method for preparing 1-10 mu m monodisperse polymer microspheres due to the simple system and no need of any stabilizer or surfactant, but has the limitations of low monomer concentration, large amount of cross-linking agent and toxic medium acetonitrile.
In order to improve the defect, subsequent researchers propose distillation precipitation polymerization, wherein a part of solvent is distilled out by using a distillation device, and a polymer is gradually separated out and grown to form polymer microspheres under the condition of no stirring, so that the precipitation polymerization is obviously improved, but the reactions are polymerization carried out by a free radical chain mechanism. This leads to the disadvantages of complicated operation, time and energy consumption in the preparation process of the polymer microspheres.
Therefore, the preparation of polymer microspheres by stepwise polymerization is the direction of the researchers' attempts, and it is a problem to be solved urgently to find reactants and reactions having the advantages of low cost, easy availability, high efficiency, time saving, energy saving, high conversion rate, no solvent or environment-friendly solvent, controllable reaction time sequence/space, simple separation, etc.
Since Sharpless proposed click chemistry in 2001, it has been a focus of research because of its unique advantages. The click chemistry has the advantages of mild reaction conditions, insensitivity to water and oxygen, easily available raw materials, capability of being used in a solvent-free or environment-friendly solvent, high conversion rate, no by-product and simplicity in separation and purification, and is widely applied to the design and synthesis of high polymer materials. From the perspective of green chemistry, click chemistry can achieve the highest atom utilization rate, and is a synthetic method with click characteristics such as high selectivity and high yield. Especially the mercapto group and alkene, alkyne, isocyanate and other monomers can carry out efficient coupling reaction under the conditions of light, heat, initiator or catalyst.
At present, the method of combining mercapto-Michael addition and precipitation polymerization is adopted, the surface of the prepared microsphere is often required to be modified in multiple steps, so that the surface of the microsphere can be provided with hydroxyl functional groups with larger polarity, and the method develops that the microsphere with the hydroxyl functional groups with larger polarity can be obtained through one-time precipitation polymerization or the multifunctional microsphere can be prepared through simple post-modification, which becomes the problem to be solved urgently.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide a polyhydroxy polymer microsphere.
In order to achieve the purpose, the invention provides the following technical scheme:
a multi-hydroxyl polymer microsphere, a preparation method thereof,
the molecular formula is as follows:
as a further improvement of the present invention,
wherein R is one of the following structures:
as another object of the present invention, there is provided a method for preparing polyhydroxylated polymer microspheres,
the method comprises the following steps: adding an acrylate reagent and dithiothreitol into a reaction vessel containing a first solvent, and stirring and mixing to form a first mixture.
Step two: the first mixture is added to a reaction vessel containing an organic base to form a second mixture.
Step three: and standing the second mixture for 5-10min, finishing the reaction, filtering, putting the precipitate in an oven at 27-30 ℃, and drying the surface to obtain the product.
As a further improvement of the present invention,
the structural formula of the dithiothreitol is as follows:
as a further improvement of the present invention,
the first solvent is methanol.
As a further improvement of the present invention,
the organic base is triethylamine.
As a further improvement of the present invention,
the ratio of functionalities in the first mixture when feeding acrylate to dithiothreitol is: 1: 1-1.05;
as a further improvement of the present invention,
in the first step, the total mass fraction of the acrylate and the dithiothreitol is 5 to 20 percent;
as a further improvement of the present invention,
in the second step, the mass fraction of the organic base in the second mixture is 20% -60%.
As another object of the present invention, there is provided a use of the polyhydroxylated polymer microspheres, and a use of the polymer microspheres as an adsorption dye.
The invention adopts typical dithiothreitol and acrylate reagent as reactants, selects methanol as solvent, and generates sulfydryl-Michael addition reaction in the presence of triethylamine to obtain the polymer microsphere.
The principle of the invention is as follows: reacting acrylate with hydroxyl-containing sulfhydryl reagent, wherein the structural formula is shown in the specificationThe acrylate of (a) is exemplified by the following reaction equation:
the other thiol reagents listed were chosen for reaction, and the reaction scheme was similar.
The invention has the beneficial effects that:
1. the method has the advantages of cheap and easily-obtained raw materials, high reaction rate, mild reaction conditions, simple and easy operation, and suitability for large-scale production;
2. the microspheres with a large number of hydroxyl functional groups can be prepared by only one-time precipitation polymerization, and the method is simple and easy to implement.
3. The polyhydroxy microspheres provide a concept for the subsequent modification of other functional groups.
4. The polymer microsphere obtained by the invention has uniform particles and can be applied to the adsorption of methyl blue dye.
Drawings
FIG. 1 is an infrared spectrum of example 1 of the present invention;
FIG. 2 is an electron micrograph of example 1 of the present invention;
FIG. 3 is a graph of UV variation at different time periods according to example 1 of the present invention;
FIG. 4 is a graph showing the color change of the absorption dye in example 1 of the present invention.
Detailed Description
The invention will be further described in detail with reference to the following examples, which are given in the accompanying drawings.
Example 1
Preparation method of polyhydroxy polymer microspheres
The method comprises the following steps: 0.35g of pentaerythritol tetraacrylate, 0.31g of dithiothreitol were added to a beaker containing 3.3g of methanol and dispersed by sonication until the mixture was completely dissolved.
Step two: the mixture was poured into a beaker containing 4ml of triethylamine and allowed to stand to slowly precipitate the formed polymer.
Step three: standing for 5-10min, reacting, filtering, washing with methanol for 2-3 times, placing precipitate in oven at 27-30 deg.C, drying surface, and collecting.
Taking a little microsphere, measuring the infrared, obtaining an infrared spectrum as shown in figure 1, and clearly seeing the wave number of 3431cm-1Stretching vibration of hydroxyl group appears at wave number of 1724cm-1The carbon-oxygen stretching vibration on the ester bond is generated at the same time of 2500cm wave number-1The stretching vibration of the sulfydryl disappears, and the product containsThe microsphere has hydroxyl and ester bonds, does not contain sulfydryl, and further proves the structure of the synthesized microsphere.
A few of SEM images are taken from the prepared microspheres, the measured morphology is shown in figure 2, and the microspheres are observed to be uniform in morphology and 1.25 mu m in size.
20mg of methylene blue is weighed, dissolved in 50mL of distilled water, and transferred to a 100mL volumetric flask to be constant volume after being completely dissolved, so as to obtain a methylene blue solution of 0.2mg/mL as a stock solution. 1mL of each stock solution was taken out by a pipette and fixed to a volume in a corresponding 10mL volumetric flask to obtain a methylene blue solution with a concentration of 0.02 mg/mL.
Placing 5mg of polyhydroxy microspheres in 5mL of methylene blue solution with the concentration of 0.02mg/mL, measuring the ultraviolet change of the polyhydroxy microspheres at the later period of time, and respectively measuring the ultraviolet change at 0h, 20h, 53h, 84h, 108h and 127h to obtain an ultraviolet change curve as shown in figure 3, wherein the ultraviolet absorption values are sequentially reduced along with the prolonging of the time until the dye is basically and completely adsorbed. After 127h is obtained through calculation, the dye amount absorbed by the microspheres is as follows: 20mg/g, the apparent dye color changes in shade as shown in FIG. 4, and becomes transparent after 127h from 0h of blue.
The reaction equation of example 1 of the present invention is:
the invention has the beneficial effects that:
1. the method has the advantages of cheap and easily-obtained raw materials, high reaction rate, mild reaction conditions, simple and easy operation, and suitability for large-scale production;
2. the microspheres with a large number of hydroxyl functional groups can be prepared by only one-time precipitation polymerization, and the method is simple and easy to implement.
3. The polyhydroxy microspheres provide a concept for the subsequent modification of other functional groups.
4. The polymer microsphere obtained by the invention has uniform particles and can be applied to the adsorption of methyl blue dye.
The above description is only a preferred embodiment of the present invention, and the protection scope of the present invention is not limited to the above embodiments, and all technical solutions belonging to the idea of the present invention belong to the protection scope of the present invention. It should be noted that modifications and embellishments within the scope of the invention may occur to those skilled in the art without departing from the principle of the invention, and are considered to be within the scope of the invention.
Claims (10)
3. the method of any one of claims 1 to 2, wherein:
the method comprises the following steps: adding an acrylate reagent and dithiothreitol into a reaction vessel containing a first solvent, and stirring and mixing to form a first mixture.
Step two: the first mixture is added to a reaction vessel containing an organic base to form a second mixture.
Step three: and standing the second mixture for 5-10min, finishing the reaction, filtering, putting the precipitate in an oven at 27-30 ℃, and drying the surface to obtain the product.
5. the method of claim 3, wherein the polyhydroxy polymer microspheres are prepared by the following steps:
the first solvent is methanol.
6. The method of claim 3, wherein the polyhydroxy polymer microspheres are prepared by the following steps:
the organic base is triethylamine.
7. The method of claim 3, wherein the polyhydroxy polymer microspheres are prepared by the following steps:
the ratio of functionalities in the first mixture when feeding acrylate to dithiothreitol is: 1: 1-1.05.
8. The method of claim 3, wherein the polyhydroxy polymer microspheres are prepared by the following steps:
in the first step, the total mass fraction of the acrylate and the dithiothreitol is 5 to 20 percent.
9. The method of claim 3, wherein the polyhydroxy polymer microspheres are prepared by the following steps:
in the second step, the mass fraction of the organic base in the second mixture is 20% -60%.
10. The use of polyhydroxyl polymeric microspheres according to claim 1, wherein: the application of the polymer microsphere as an adsorption dye.
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN104530280A (en) * | 2015-01-13 | 2015-04-22 | 浙江大学 | Method for preparing monodispersed polymer gel micro-spheres through nonaqueous emulsion polymerization system |
US20160039961A1 (en) * | 2014-08-05 | 2016-02-11 | The Regents Of The University Of Colorado, A Body Corporate | Monodisperse microspheres and method of preparing same |
CN105418872A (en) * | 2015-12-03 | 2016-03-23 | 西北工业大学 | Method for preparing functionalized crosslinked monodisperse polymer microspheres through one-step dispersion polymerization |
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US20160039961A1 (en) * | 2014-08-05 | 2016-02-11 | The Regents Of The University Of Colorado, A Body Corporate | Monodisperse microspheres and method of preparing same |
CN104530280A (en) * | 2015-01-13 | 2015-04-22 | 浙江大学 | Method for preparing monodispersed polymer gel micro-spheres through nonaqueous emulsion polymerization system |
CN105418872A (en) * | 2015-12-03 | 2016-03-23 | 西北工业大学 | Method for preparing functionalized crosslinked monodisperse polymer microspheres through one-step dispersion polymerization |
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