CN114716617B - High-hydrophilicity PVDF material and preparation method thereof - Google Patents
High-hydrophilicity PVDF material and preparation method thereof Download PDFInfo
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- CN114716617B CN114716617B CN202210472687.3A CN202210472687A CN114716617B CN 114716617 B CN114716617 B CN 114716617B CN 202210472687 A CN202210472687 A CN 202210472687A CN 114716617 B CN114716617 B CN 114716617B
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- 239000002033 PVDF binder Substances 0.000 title claims abstract description 77
- 229920002981 polyvinylidene fluoride Polymers 0.000 title claims abstract description 77
- 239000000463 material Substances 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title abstract description 6
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 40
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 14
- 239000007795 chemical reaction product Substances 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- -1 anthracene free radical Chemical class 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000003381 stabilizer Substances 0.000 claims description 7
- 239000003999 initiator Substances 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 5
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 claims description 4
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 4
- 239000002245 particle Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- SKXCTCCZTWNYMD-UHFFFAOYSA-N 1,2-bis(ethenyl)anthracene Chemical compound C1=CC=CC2=CC3=C(C=C)C(C=C)=CC=C3C=C21 SKXCTCCZTWNYMD-UHFFFAOYSA-N 0.000 claims description 2
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 claims description 2
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims 1
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 9
- 150000008064 anhydrides Chemical group 0.000 abstract description 3
- 239000000178 monomer Substances 0.000 abstract description 2
- 230000009257 reactivity Effects 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 13
- 239000000203 mixture Substances 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 238000009864 tensile test Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OGOYZCQQQFAGRI-UHFFFAOYSA-N 9-ethenylanthracene Chemical compound C1=CC=C2C(C=C)=C(C=CC=C3)C3=CC2=C1 OGOYZCQQQFAGRI-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920006113 non-polar polymer Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920006112 polar polymer Polymers 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F259/00—Macromolecular compounds obtained by polymerising monomers on to polymers of halogen containing monomers as defined in group C08F14/00
- C08F259/08—Macromolecular compounds obtained by polymerising monomers on to polymers of halogen containing monomers as defined in group C08F14/00 on to polymers containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Graft Or Block Polymers (AREA)
Abstract
The invention discloses a high-hydrophilicity PVDF material and a preparation method thereof, which are prepared by Maleic Anhydride (MAH) high-temperature melt grafting polyvinylidene fluoride (PVDF). According to the invention, the PVDF is grafted and modified by introducing MAH, and the hydrophilicity and the miscibility of other polymers of the PVDF can be effectively enhanced by utilizing the reactivity of anhydride groups on MAH monomers and the polarity of MAH, so that the application of the PVDF is expanded.
Description
Technical Field
The invention relates to the technical field of grafting of polymer composite materials, in particular to a high-hydrophilicity PVDF material, and a preparation method and application thereof.
Background
Polyvinylidene fluoride (PVDF) is an important semi-crystalline fluoropolymer. PVDF has attracted considerable academic and industrial attention due to its excellent heat resistance, weather resistance, processability and irradiation resistance. PVDF consists of- (CH 2-CF 2) -repeat units and has a relative density of 1.75 to 1.78g/cm 3 The long term use temperatures of-40 to 150 ℃ and the obtaining of high performance PVDF composites by blending PVDF with other polymers is an economical and simple strategy. However, overall improvement is limited due to poor miscibility between PVDF and these polymers.
In addition, the PVDF film has very low surface energy, which results in a film with strong hydrophobicity and poor adhesion of PVDF to metal substrates, thus not only limiting the application of PVDF to films but also limiting the development of PVDF coatings. Maleic Anhydride (MAH) is a polar compound containing many functional groups, especially unsaturated double bonds, which can be easily polymerized with other polymers by adding reagents or by irradiation. The anhydride groups may also react with hydroxyl, carboxyl, amine, and other functional groups. Therefore, MAH functionalization of some non-polar polymers is beneficial to increasing their compatibility with polar polymers, improving the adhesion of the material and the interaction of the filler with the polymer. Obviously, the use of MAH to modify PVDF is an effective strategy for preparing high-hydrophilicity PVDF materials, and the miscibility of modified PVDF with other polymers can be correspondingly improved, however, the use of MAH to modify PVDF has been reported recently in the past decades.
Disclosure of Invention
Based on the problems of the prior art, the invention provides a high-hydrophilicity PVDF material and a preparation method thereof, aiming at grafting PVDF by using MAH of a reactive group, thereby improving the hydrophilicity of PVDF and the miscibility with other polymers.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
a preparation method of a PVDF material with high hydrophilicity is characterized in that: the high-hydrophilicity PVDF material is prepared by maleic anhydride MAH high-temperature melt grafting polyvinylidene fluoride PVDF, and specifically comprises the following steps:
s1, drying MAH and PVDF in an oven;
s2, turning on a torque rheometer and setting required parameters (reaction temperature and rotating speed); after the parameters of the torque rheometer reach set values, placing the dried MAH and PVDF into the torque rheometer, and adding an initiator and an anthracene free radical stabilizer into the torque rheometer to react; after the reaction is finished, the torque rheometer is closed, and the reaction product is taken out and cooled;
s3, crushing the cooled reaction product into powder and purifying to obtain the target product high-hydrophilicity PVDF material.
Further, the molecular weight of the PVDF is 80000-200000, and the PVDF is particles or powder.
Further, the drying temperature in the step S1 is 50-80 ℃ and the drying time is 12-24 hours.
Further, the reaction temperature in the step S2 is 190-210 ℃, the reaction time is 5-7min, and the rotating speed of the torque rheometer is 40-60rpm.
Further, in step S2, the initiator is at least one of Benzoyl Peroxide (BPO), dicumyl peroxide (DCP), benzoyl tert-Butyl Peroxide (BPB) and methyl ethyl ketone peroxide, and the anthracene-based radical stabilizer is at least one of divinyl anthracene, nonaethyl anthracene and distyryl anthracene.
Further, in step S2, the mass ratio of PVDF to MAH is 90-97%: 10 to 3 percent of initiator accounting for 0.1 to 0.5 percent of the total mass of PVDF and MAH, and the anthracene free radical stabilizer accounting for 0.1 to 0.5 percent of the total mass of PVDF and MAH.
Further, the crushing described in step S3 is a cryogenic crushing, and the equipment used is a cryogenic crusher, because the product of the reaction is a plastic material, which cannot be crushed sufficiently by conventional crushers.
Further, the purification method in step S3 is as follows: adding the reaction product into N, N-Dimethylformamide (DMF), dimethyl sulfoxide (DMSO) or N, N-Dimethylacetamide (DMAC), and stirring for 2 hours at 40-60 ℃ in an oil bath kettle to dissolve the reaction product; and then pouring the solution into excessive ethanol for precipitation, standing, filtering, fully washing with acetone, and drying.
The beneficial effects of the invention are as follows:
according to the invention, the PVDF is grafted and modified by introducing MAH under the action of the anthracene free radical stabilizer, and the hydrophilicity and the miscibility of other polymers of the PVDF can be effectively enhanced by utilizing the reactivity of anhydride groups on MAH monomers and the polarity of MAH, so that the application of the PVDF is expanded.
Drawings
FIG. 1 is a graph showing the water contact angle of the products obtained in example 1 and comparative example 1, wherein (a) is pure PVDF, (b) is PVDF/MAH obtained in comparative example 1, and (c) is PVDF-g-MAH obtained in example 1;
FIG. 2 is a drawing showing tensile test of the products obtained in example 1 and comparative example 1 of the present invention;
FIG. 3 is an XRD pattern of the products obtained in example 1 and comparative example 1 of the present invention;
FIG. 4 is a Fourier infrared spectrum of the product obtained in example 1 and comparative example 1 of the present invention.
Detailed Description
The following describes in detail the examples of the present invention, which are implemented on the premise of the technical solution of the present invention, and detailed embodiments and specific operation procedures are given, but the scope of protection of the present invention is not limited to the following examples.
Example 1
This example prepared PVDF-g-MAH material as follows
S1, drying MAH and PVDF (with molecular weight of 150000 and particles) in an oven at 80 ℃ for 20h to remove excessive moisture in the material.
S2, turning on a torque rheometer and setting required parameters (reaction temperature 200 ℃ and rotating speed 50 rpm); after the parameters of the torque rheometer reach the set values, placing the dried MAH (2 g) and PVDF (20 g) into the torque rheometer, adding DCP (0.05 g), BPO (0.05 g) and 9-vinyl anthracene (0.05 g) into the mixture, and reacting for 6min at 200 ℃; after the reaction is completed, the torque rheometer is turned off, and the reaction product is taken out and cooled.
(3) Placing the cooled reaction product into a cryogenic crusher for full crushing to prepare powder; adding the powder into a round bottom flask, and stirring for 2 hours at 50 ℃ in an oil bath to dissolve a reaction product; and then pouring the solution into excessive ethanol to separate out, standing, carrying out suction filtration, fully washing with acetone, and drying to obtain the target product, namely the high-hydrophilicity PVDF material, namely PVDF-g-MAH.
Comparative example 1
The comparative example prepared a MAH and PVDF blend material as follows:
s1, drying MAH and PVDF (with molecular weight of 150000 and particles) in an oven at 80 ℃ for 20h to remove excessive moisture in the material.
S2, turning on a torque rheometer and setting required parameters (reaction temperature 200 ℃ and rotating speed 50 rpm); after the parameters of the torque rheometer reach set values, placing the dried MAH (2 g) and PVDF (20 g) into the torque rheometer, and reacting for 6min at 200 ℃; after the reaction is completed, the torque rheometer is turned off, and the reaction product is taken out and cooled.
(3) Placing the cooled reaction product into a cryogenic crusher for full crushing to prepare powder; adding the powder into a round bottom flask, and stirring for 2 hours at 50 ℃ in an oil bath to dissolve a reaction product; and then pouring the solution into excessive ethanol to separate out, standing, carrying out suction filtration, fully washing with acetone, and drying to obtain the MAH and PVDF blend material, namely PVDF/MAH.
FIG. 1 is a graph showing the water contact angle of the products obtained in example 1 and comparative example 1, wherein (a) is pure PVDF, (b) is PVDF/MAH obtained in comparative example 1, and (c) is PVDF-g-MAH obtained in example 1. From the figure, it can be seen that the hydrophilicity of PVDF-g-MAH is much better than that of PVDF/MAH, which suggests that MAH grafting PVDF can significantly improve the hydrophilicity of PVDF.
The samples obtained in example 1 and comparative example 1 were subjected to tensile test, and the results are shown in fig. 2. It can be seen that the elongation at break of PVDF-g-MAH obtained in example 1 was 502.1MPa and that of PVDF/MAH obtained in comparative example 1 was 353.4MPa. It can be seen that the elongation at break of the grafted material is significantly increased compared to the direct blending.
Fig. 3 is an XRD pattern of the product obtained in example 1 and comparative example 1, from which it can be seen that MAH grafting has no effect on the crystalline form of PVDF, whereas the crystalline form of PVDF in the blend of PVDF and MAH is affected to some extent, but no form of MAH is present.
FIG. 4 is a Fourier infrared spectrum of the product obtained in example 1 and comparative example 1, from which it can be seen that PVDF-g-MAH is present at 1783cm compared to PVDF/MAH -1 And 1850cm -1 There are distinct absorption peaks on the left and right, which are characteristic absorption peaks for MAH, further indicating successful grafting of MAH onto PVDF.
The foregoing is illustrative only and is not intended to limit the present invention, and any modifications, equivalents, improvements and modifications falling within the spirit and principles of the invention are intended to be included within the scope of the present invention.
Claims (6)
1. A method for improving the hydrophilicity of PVDF, characterized by: the maleic anhydride MAH is subjected to high-temperature melt grafting to polyvinylidene fluoride PVDF so as to improve the hydrophilicity of the PVDF and obtain a high-hydrophilicity PVDF material, which comprises the following steps:
s1, drying MAH and PVDF in an oven;
s2, placing the dried MAH and PVDF in a torque rheometer, adding an initiator and an anthracene free radical stabilizer into the torque rheometer, and reacting at 190-210 ℃ for 5-7min at 40-60rpm; after the reaction is finished, the torque rheometer is closed, and the reaction product is taken out and cooled;
the initiator is at least one of benzoyl peroxide, dicumyl peroxide, tert-butyl benzoyl peroxide and methyl ethyl ketone peroxide, and the anthracene free radical stabilizer is at least one of divinyl anthracene, nonaethyl anthracene and distyryl anthracene;
the mass ratio of PVDF to MAH is 90-97%: 10 to 3 percent of initiator accounting for 0.1 to 0.5 percent of the total mass of PVDF and MAH, and 0.1 to 0.5 percent of anthracene free radical stabilizer accounting for the total mass of PVDF and MAH;
s3, crushing the cooled reaction product into powder and purifying to obtain the target product high-hydrophilicity PVDF material.
2. The method according to claim 1, characterized in that: the molecular weight of PVDF is 80000-200000, and PVDF is particles or powder.
3. The method according to claim 1, characterized in that: the drying temperature in the step S1 is 50-80 ℃ and the drying time is 12-24h.
4. The method according to claim 2, characterized in that: the crushing in the step S3 is cryogenic crushing.
5. The method according to claim 2, characterized in that: the purification method in the step S3 is as follows: adding the reaction product into DMF, DMSO or DMAC, and stirring for 2 hours at 40-60 ℃ in an oil bath pot to dissolve the reaction product; and then pouring the solution into excessive ethanol for precipitation, standing, filtering, fully washing with acetone, and drying.
6. A PVDF material of high hydrophilicity obtained by the method of any one of claims 1 to 5.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07173447A (en) * | 1993-10-28 | 1995-07-11 | Asahi Glass Co Ltd | Bondable fluoropolymer and laminate thereof |
| CN106674406A (en) * | 2016-12-31 | 2017-05-17 | 山东华夏神舟新材料有限公司 | Preparation method and modification method of flexible low-melting point vinylidene fluoride copolymer |
| CN107213803A (en) * | 2017-05-08 | 2017-09-29 | 武汉理工大学 | A kind of Kynoar film surface grafting coats composite modifying method |
| CN110975649A (en) * | 2019-11-19 | 2020-04-10 | 江苏大孚膜科技有限公司 | Modified polyvinylidene fluoride ultrafiltration membrane and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2864542B1 (en) * | 2003-12-29 | 2007-02-23 | Arkema | METHOD OF GRAFTING FLUORINATED POLYMER AND MULTILAYER STRUCTURES COMPRISING THE GRAFT POLYMER |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07173447A (en) * | 1993-10-28 | 1995-07-11 | Asahi Glass Co Ltd | Bondable fluoropolymer and laminate thereof |
| CN106674406A (en) * | 2016-12-31 | 2017-05-17 | 山东华夏神舟新材料有限公司 | Preparation method and modification method of flexible low-melting point vinylidene fluoride copolymer |
| CN107213803A (en) * | 2017-05-08 | 2017-09-29 | 武汉理工大学 | A kind of Kynoar film surface grafting coats composite modifying method |
| CN110975649A (en) * | 2019-11-19 | 2020-04-10 | 江苏大孚膜科技有限公司 | Modified polyvinylidene fluoride ultrafiltration membrane and preparation method thereof |
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