CN113788945A - A kind of polyethylene glycol diacrylate polymer microgel and its preparation method and application - Google Patents
A kind of polyethylene glycol diacrylate polymer microgel and its preparation method and application Download PDFInfo
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- CN113788945A CN113788945A CN202110933073.6A CN202110933073A CN113788945A CN 113788945 A CN113788945 A CN 113788945A CN 202110933073 A CN202110933073 A CN 202110933073A CN 113788945 A CN113788945 A CN 113788945A
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- 239000002202 Polyethylene glycol Substances 0.000 title claims abstract description 33
- 229920001223 polyethylene glycol Polymers 0.000 title claims abstract description 33
- 229920000642 polymer Polymers 0.000 title claims abstract description 31
- 125000004386 diacrylate group Chemical group 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 7
- 239000003774 sulfhydryl reagent Substances 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 7
- 150000007530 organic bases Chemical class 0.000 claims description 6
- 239000002244 precipitate Substances 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 2
- 239000002994 raw material Substances 0.000 abstract description 6
- 239000004005 microsphere Substances 0.000 description 17
- 230000006872 improvement Effects 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 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 5
- 230000008859 change Effects 0.000 description 5
- 229960000907 methylthioninium chloride Drugs 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 238000012673 precipitation polymerization Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- 239000000017 hydrogel Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000012674 dispersion polymerization Methods 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000001878 scanning electron micrograph Methods 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000012798 spherical particle Substances 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000002604 ultrasonography 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- 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
- B01J20/262—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. obtained by polycondensation
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- B—PERFORMING OPERATIONS; TRANSPORTING
- 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
- B01J20/28—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
- B01J20/28047—Gels
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Analytical Chemistry (AREA)
- Dispersion Chemistry (AREA)
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- Polymers & Plastics (AREA)
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Abstract
本发明公开了一种聚乙二醇二丙烯酸酯聚合物微凝胶的制备方法及其应用，其制备方法是：将聚乙二醇二丙烯酸酯和巯基试剂在室温条件下，溶于甲醇中，在三乙胺存在条件下，得到聚合物微凝胶。本发明的优点是，所用到的试剂及原料常见易得，反应速率快，反应条件温和，操作方法简单，在高分子领域内具有广泛的应用前景。
The invention discloses a preparation method and application of a polyethylene glycol diacrylate polymer microgel. The preparation method comprises the following steps: dissolving polyethylene glycol diacrylate and a sulfhydryl reagent in methanol at room temperature , in the presence of triethylamine to obtain polymer microgels. The invention has the advantages that the used reagents and raw materials are common and readily available, the reaction rate is fast, the reaction conditions are mild, the operation method is simple, and has wide application prospects in the polymer field.
Description
Technical Field
The invention belongs to the field of polymer synthesis, and particularly relates to a polyethylene glycol diacrylate polymer microgel and a preparation method and application thereof.
Background
The microgel (namely, microsphere) is one of hydrogels, is similar to macroscopic hydrogel, can freely swell in water, but is insoluble in water, and is a functional material with a three-dimensional network structure; the microgel has micron or nanometer size, the particle size of common particles is between 1 and 5000nm, and the microgel also has a cross-linked network structure and can be swelled by a solvent. In practical applications, the microgel and the macroscopic hydrogel have the same characteristics in application due to different sizes and structures. For microgel, the balance between the hydrophilic action of a polymer chain segment and the entropy elasticity of a polymer network exists inside the microgel, and when the microgel is stimulated by the outside, the balance moves, and the particle size changes remarkably, namely volume phase transformation exists; for temperature sensitive microgels, at a certain temperature, there is a significant change in volume, i.e., a "volume-to-phase transition temperature". The microgel has wide application prospect in the aspects of drug controlled release, coating, preparation of nano hybrid materials, optics, sensors, microgel profile control and flooding systems and the like.
The preparation method of the microgel and the preparation method of the polymer microsphere generally comprise the preparation of the microsphere which takes a monomer as a raw material and a polymer as a raw material and the preparation of a high-molecular composite microsphere. The general preparation method using monomers as raw materials comprises the following steps: suspension polymerization, emulsion polymerization, dispersion polymerization, precipitation polymerization, and the like. Although the suspension polymerization can obtain micron spherical particles, the prepared polymer microspheres have the defect of wide particle size distribution; emulsion polymerization typically results in monodisperse submicron spherical particles, but requires the use of appropriate stabilizers or surfactants, and the emulsifiers are not subsequently easily removed from the product; the dispersion polymerization requires adding a stabilizer into a system; the precipitation polymerization method developed by Stover et al (Journal of Polymer Science Part A: Polymer Chemistry, 1993, 31: 3257-3263) does not require a stabilizer or a surfactant, which provides a convenient and direct approach for the synthesis of monodisperse crosslinked microspheres.
Early precipitation polymerization was carried out using acetonitrile as solvent, which is highly toxic, and the monomers of choice were usually styrenic monomers with strong hydrophobicity, such as: styrene, divinylbenzene, etc., and also acrylate monomers, such as: acrylonitrile, acrylamide, and the like. Acrylate monomers are usually copolymerized with divinylbenzene to form polymeric microspheres, and such microspheres often fail to provide a broader range of polarity and functionality in practical applications. Therefore, as the microgel, a monomer or a polymer with higher polarity is often selected as a reactant, and the prepared microsphere has the performance of the microgel. With the development, researchers have prepared poly (acrylamide-co-methylenebisacrylamide) microgel by precipitation polymerization method using ethanol as solvent, but because ethanol has affinity with acrylic acid, it needs to be further stabilized after adding a small amount of acrylic acid. Therefore, it is an urgent need to develop microspheres that can be used for preparing microgel by precipitation polymerization without adding any other reagents to stabilize the generated microspheres.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide a polyethylene glycol diacrylate polymer microgel.
In order to achieve the purpose, the invention provides the following technical scheme:
a polyethylene glycol diacrylate polymer microgel,
the molecular formula of the microgel is as follows:
as a further improvement of the present invention,
r is one of the following structural formulas
As another object of the present invention, there is provided a method for preparing a microgel of a polyethylene glycol diacrylate polymer,
the method comprises the following steps:
the method comprises the following steps: adding polyethylene glycol diacrylate and a sulfydryl reagent into a reaction vessel filled with 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 10-30min, 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 polyethylene glycol diacrylate 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 sulfhydryl reagent is a compound with the following structural formula:
as a further improvement of the present invention,
the ratio of the functionalities of the polyethylene glycol diacrylate to the mercapto agent in the first mixture is: 1: 1-1.05.
As a further improvement of the present invention,
in the first mixed solution, the mass fraction of the sum of the mass of the polyethylene glycol diacrylate and the mass of the mercapto reagent is 5-20%; the mass fraction of the organic base in the second mixture is 20% to 60%.
As another object of the invention, the invention provides an application of the polyethylene glycol diacrylate polymer microgel, and the microgel is used as an absorption dye.
The principle of the invention is as follows: reacting polyethylene glycol and acrylate with mercapto reagent, wherein the molecular formula is
the other thiol reagents listed were chosen for reaction, and the reaction scheme was similar.
The invention has the beneficial effects that: 1. the raw materials used in the invention are cheap and easily available, a typical mercapto-Michael addition reaction mechanism is adopted for polymerization, the reaction rate is high, the reaction condition is mild, and the operation is simple and easy to implement;
2. the reaction raw material adopted by the invention is the polyethylene glycol diacrylate, and the chain segment of the contained polyethylene glycol is a material with excellent biocompatibility and is relatively environment-friendly.
3. The microsphere particles obtained by the method are uniform and have good performance on dye adsorption.
Drawings
FIG. 1 is an infrared spectrum of a microgel provided in example 1 of the present invention;
FIG. 2 is a scanning electron micrograph of a microgel provided in example 1 of the present invention;
FIG. 3 is a standard curve of a methylene blue solution provided in example 1 of the present invention;
FIG. 4 is a graph showing the variation of UV in methylene blue solution at different times after microgel addition as provided in example 1 of the present invention;
FIG. 5 is a graph showing the change in apparent color of the system before and after the microgel provided in example 1 of the present invention adsorbs a dye.
Detailed Description
The present invention will be described in further detail with reference to the accompanying drawings and examples.
Example 1
Preparation method of polyethylene glycol diacrylate polymer microgel
The method comprises the following steps: 0.5g of polyethylene glycol diacrylate (Mn 1000) and 0.122g of pentaerythritol tetrakis (3-mercaptopropionate) were added to a beaker containing 3.11g of methanol and dispersed by ultrasound until the mixture was completely dissolved.
Step two: the mixture was added to a beaker containing 4ml of triethylamine, and the mixture was allowed to stand to slowly precipitate a polymer formed.
Step three: standing for 10-30min, reacting, filtering, placing the precipitate in an oven at 27-30 deg.C, drying, and collecting.
Taking a little of microspheres, measuring the infrared of the microspheres to obtain an infrared spectrum as shown in figure 1, wherein C-H stretching vibration appears at a wave number of 2867cm-1, C ═ O stretching vibration appears at a wave number of 1735cm-1 on an ester bond, and C-O stretching vibration appears at a wave number of 1088cm-1, so that the product contains the ester bond, and the structure of the synthesized microspheres is further proved.
A few of SEM images are taken for the prepared microspheres, the measured morphology is shown in figure 2, and the microspheres are observed to be uniform in morphology and have the size of 3-4 microns.
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. Taking 1mL, 0.75mL, 0.5mL, 0.25mL and 0.125mL of stock solutions by using a pipette, fixing the volume in a corresponding 10mL volumetric flask, and measuring the ultraviolet absorption to obtain a standard curve, as shown in FIG. 3.
Placing 5mg of polyethylene glycol microgel in 5mL of methylene blue solution with the concentration of 0.02mg/mL, measuring the ultraviolet change of the microgel at an over-period of time, and obtaining an ultraviolet change curve as shown in FIG. 4, wherein it can be seen that the ultraviolet absorption values are sequentially reduced along with the time extension, and the change of the ultraviolet absorption intensity of the system is not obvious after 84h, which shows that the dye adsorption is saturated, and the dye quantity adsorbed by the microgel is as follows after 84h is obtained through calculation: 13.4mg/g, the apparent dye color changed from dark blue to light green as shown in FIG. 5.
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)
1. A polyethylene glycol diacrylate polymer microgel, which is characterized in that:
the molecular formula of the microgel is as follows:
2. the polyethylene glycol diacrylate polymer microgel of claim 1, wherein:
r is one of the following structural formulas
3. The method for preparing a polyethylene glycol diacrylate polymer microgel as described in claim 1 or 2, wherein:
the method comprises the following steps:
the method comprises the following steps: adding polyethylene glycol diacrylate and a sulfydryl reagent into a reaction vessel filled with 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 10-30min, finishing the reaction, filtering, putting the precipitate in an oven at 27-30 ℃, and drying the surface to obtain the product.
4. The method for preparing a polyethylene glycol diacrylate polymer microgel according to claim 3, wherein: the structural formula of the polyethylene glycol diacrylate is as follows:
5. the method for preparing a polyethylene glycol diacrylate polymer microgel according to claim 3, wherein:
the first solvent is methanol.
6. The method for preparing a polyethylene glycol diacrylate polymer microgel according to claim 3, wherein:
the organic base is triethylamine.
7. The method for preparing a polyethylene glycol diacrylate polymer microgel according to claim 3, wherein:
the sulfhydryl reagent is a compound with the following structural formula:
8. the method for preparing a polyethylene glycol diacrylate polymer microgel according to claim 3, wherein:
the ratio of the functionalities of the polyethylene glycol diacrylate to the mercapto agent in the first mixture is: 1: 1-1.05.
9. The method for preparing a polyethylene glycol diacrylate polymer microgel according to claim 3, wherein:
in the first mixed solution, the mass fraction of the sum of the mass of the polyethylene glycol diacrylate and the mass of the mercapto reagent is 5-20%;
the mass fraction of the organic base in the second mixture is 20% to 60%.
10. The use of a polyethylene glycol diacrylate polymer microgel as claimed in claim 1 or 2, wherein:
the microgel is used for adsorbing dye.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102718991A (en) * | 2012-04-05 | 2012-10-10 | 天津大学 | High strength injectable hydrogel and preparation method thereof |
| 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 |
| CN107635655A (en) * | 2015-01-06 | 2018-01-26 | Lvmh研究公司 | Poly(ethylene glycol) methacrylate microgel, preparation method and use |
| CN110172115A (en) * | 2019-04-19 | 2019-08-27 | 华中科技大学 | A kind of method for preparing polymer electrolytes and its application |
-
2021
- 2021-08-13 CN CN202110933073.6A patent/CN113788945A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102718991A (en) * | 2012-04-05 | 2012-10-10 | 天津大学 | High strength injectable hydrogel and preparation method thereof |
| 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 |
| CN107635655A (en) * | 2015-01-06 | 2018-01-26 | Lvmh研究公司 | Poly(ethylene glycol) methacrylate microgel, preparation method and use |
| CN110172115A (en) * | 2019-04-19 | 2019-08-27 | 华中科技大学 | A kind of method for preparing polymer electrolytes and its application |
Non-Patent Citations (1)
| Title |
|---|
| 张鹏，王兆华: "丙烯酸树脂防腐蚀涂料及应用", 上海：华东理工大学出版社, pages: 275 * |
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