CN113388110A - Polyarylethersulfone modified material and preparation method thereof - Google Patents
Polyarylethersulfone modified material and preparation method thereof Download PDFInfo
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- CN113388110A CN113388110A CN202110659937.XA CN202110659937A CN113388110A CN 113388110 A CN113388110 A CN 113388110A CN 202110659937 A CN202110659937 A CN 202110659937A CN 113388110 A CN113388110 A CN 113388110A
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- polyarylethersulfone
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- 239000000463 material Substances 0.000 title claims abstract description 59
- 229920000110 poly(aryl ether sulfone) Polymers 0.000 title claims abstract description 56
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000010438 heat treatment Methods 0.000 claims abstract description 16
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 239000012024 dehydrating agents Substances 0.000 claims abstract description 9
- 238000010992 reflux Methods 0.000 claims abstract description 9
- 239000011261 inert gas Substances 0.000 claims abstract description 7
- 238000002156 mixing Methods 0.000 claims abstract description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 229910052786 argon Inorganic materials 0.000 claims description 5
- PLVUIVUKKJTSDM-UHFFFAOYSA-N 1-fluoro-4-(4-fluorophenyl)sulfonylbenzene Chemical compound C1=CC(F)=CC=C1S(=O)(=O)C1=CC=C(F)C=C1 PLVUIVUKKJTSDM-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- -1 alkali metal salt Chemical class 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims description 2
- 239000012153 distilled water Substances 0.000 claims description 2
- 239000001307 helium Substances 0.000 claims description 2
- 229910052734 helium Inorganic materials 0.000 claims description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 230000007123 defense Effects 0.000 abstract description 4
- 230000036541 health Effects 0.000 abstract description 4
- 229920012287 polyphenylene sulfone Polymers 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 125000006267 biphenyl group Chemical group 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000007599 discharging Methods 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229920006351 engineering plastic Polymers 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VOAAEKKFGLPLLU-UHFFFAOYSA-N (4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1 VOAAEKKFGLPLLU-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 229920012266 Poly(ether sulfone) PES Polymers 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920013655 poly(bisphenol-A sulfone) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Images
Classifications
-
- 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
- C08G75/20—Polysulfones
- C08G75/23—Polyethersulfones
Abstract
The invention discloses a polyarylethersulfone modified material and a preparation method thereof, wherein the preparation method of the polyarylethersulfone modified material comprises the following steps: mixing 4,4 '-bis (4-hydroxyphenyl) diphenylsulfone, 4' -difluorodiphenylsulfone and a catalyst under an inert gas atmosphere, and then adding a dehydrating agent to obtain an intermediate mixture; heating the intermediate mixture to 130-150 ℃, refluxing for 2-3h, heating to 180-200 ℃, and reacting for 4-5h to obtain the polyarylethersulfone modified material. The polyarylethersulfone modified material prepared by the invention has better heat resistance and mechanical property, and can meet the requirements of the fields of national defense and military industry, aerospace, electronic and electric appliances, medical treatment and health and the like.
Description
Technical Field
The invention relates to the field of polymer synthesis, in particular to a polyether sulphone modified material and a preparation method thereof.
Background
The polyarylethersulfone resin is a special engineering plastic with excellent comprehensive performance, and at present, the widely applied polyarylethersulfone resin mainly comprises three resins, namely bisphenol A Polysulfone (PSF), Polyethersulfone (PES) and polyphenylenesulfone (PPSU).
As an important member of the special engineering plastic family, the PPESE resin is widely applied to the high-tech fields of national defense war industry, aerospace, electronic appliances, medical treatment and health care and the like by virtue of higher heat resistance level, excellent mechanical property and flame retardance and good processability, but the rapid development of the fields puts more rigorous requirements on the properties of the material such as thermal stability, mechanical strength and the like, and the application of the traditional PPESE resin in the fields cannot keep pace with the era due to the limitation of glass transition temperature and amorphous aggregation structure, so that a plurality of scholars are dedicated to designing the PPESE polymer with more excellent synthesis force and thermal property in recent years.
Accordingly, there is still a need for advancement and development of the prior art.
Disclosure of Invention
The invention provides a polyarylethersulfone modified material and a preparation method thereof aiming at solving the technical problem that the heat resistance and mechanical property of the existing polyarylethersulfone material can not meet the industrial requirement.
In order to achieve the purpose, the invention is realized by the following technical scheme:
a preparation method of a polyarylethersulfone modified material comprises the following steps:
mixing 4,4 '-bis (4-hydroxyphenyl) diphenylsulfone, 4' -difluorodiphenylsulfone and a catalyst under an inert gas atmosphere, and then adding a dehydrating agent to obtain an intermediate mixture;
heating the intermediate mixture to 130-150 ℃, refluxing for 2-3h, heating to 180-200 ℃, and reacting for 4-5h to obtain the polyarylethersulfone modified material.
The preparation method of the polyarylethersulfone modified material comprises the following step of mixing 4,4 '-bis (4-hydroxyphenyl) diphenylsulfone, 4' -difluorodiphenylsulfone and a catalyst in a ratio of 1:1:1.1-1.2 in parts by mole.
The preparation method of the polyarylethersulfone modified material is characterized in that the catalyst is alkali metal salt.
The preparation method of the polyarylether sulfone modified material comprises the step of preparing a dehydrating agent, wherein the dehydrating agent is a mixed solution of sulfolane and methylbenzene.
The preparation method of the polyarylethersulfone modified material comprises the following steps of, by volume, 70-80% of sulfolane and 20-30% of toluene in the dehydrating agent.
The preparation method of the polyarylethersulfone modified material comprises the step of preparing a polyether sulfone modified material, wherein the inert gas is one of nitrogen, argon and helium.
The preparation method of the polyarylethersulfone modified material comprises the following steps of heating the intermediate mixture to 130-150 ℃, refluxing for 2-3h, raising the temperature gradient to 180-200 ℃, and reacting for 4-5h to obtain the polyarylethersulfone modified material:
and repeatedly cleaning the polyarylethersulfone modified material by adopting an organic solvent and distilled water.
The preparation method of the polyarylethersulfone modified material comprises the step of adding an organic solvent, wherein the organic solvent is one of ethanol, diethyl ether and dichloromethane.
In addition, the invention also provides a polyarylethersulfone modified material which is prepared by adopting the preparation method of the polyarylethersulfone composite material.
Has the advantages that: the polyarylethersulfone modified material prepared by the invention can effectively improve the mechanical property and the heat resistance of the prepared polyarylethersulfone modified material by introducing a large amount of biphenyl groups.
Drawings
FIG. 1 is a schematic flow chart of a method for preparing a modified polyarylethersulfone material of the present invention.
Detailed Description
To facilitate an understanding of the present application, the present application will now be described more fully with reference to the accompanying drawings. Preferred embodiments of the present application are given in the accompanying drawings. This application may, however, be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. The terminology used herein in the description of the present application is for the purpose of describing particular embodiments only and is not intended to be limiting of the application.
In the present invention, the 4, 4' -bis (4-hydroxyphenyl) diphenylsulfone used can be prepared by the following method:
mixing a catalyst, sodium bicarbonate, 4 '-dichlorodiphenyl sulfone and p-methoxyphenylboronic acid, adding 1, 4-dioxane and deionized water in the atmosphere of inert gas, and reacting at 100 ℃ for 3-4 days to obtain the 4, 4' -bis (4-hydroxyphenyl) diphenyl sulfone.
In the invention, the adopted 4, 4' -bis (4-hydroxyphenyl) diphenyl sulfone is provided with a rodlike rigid group biphenyl group with a simple structure, and the biphenyl group has excellent stability and good symmetry.
Further, as shown in fig. 1, the preparation method of the modified material of polyarylethersulfone comprises the steps of:
s10, mixing 4,4 '-bis (4-hydroxyphenyl) diphenyl sulfone, 4' -difluorodiphenyl sulfone and a catalyst in an inert gas atmosphere, and then adding a dehydrating agent to obtain an intermediate mixture;
s20, heating the intermediate mixture to 150 ℃ for refluxing for 2-3h, then heating to 200 ℃ for reacting for 4-5h to obtain the polyarylethersulfone modified material.
According to the invention, a large amount of biphenyl groups are introduced, so that the mechanical property and the heat resistance of the prepared polyarylether sulfone modified material can be effectively improved, and the modified polyarylether sulfone modified material can meet the requirements of the fields of national defense and military industry, aerospace, electronic and electric appliances, medical treatment and health care and the like.
The following is a further explanation of the modified polyarylethersulfone material and the preparation method thereof according to the present invention by specific examples:
example 1
Adding 0.05mol of 4,4 '-bis (4-hydroxyphenyl) diphenyl sulfone, 0.05mol of 4, 4' -difluorodiphenyl sulfone and 0.06mol of potassium carbonate into a three-neck flask in sequence, then adding 80mL of sulfolane and 25mL of toluene, slowly heating the system to 150 ℃ under the protection of argon, refluxing for 3 hours, discharging the toluene and the excess water, then adopting a gradient heating mode to raise the temperature to 200 ℃, reacting for 4 hours, obtaining a reaction product after the viscosity of the system is not changed any more, and washing the reaction product for multiple times by adopting deionized water and ethanol to obtain the white polyarylether sulfone modified material.
Example 2
Adding 0.06mol of 4,4 '-bis (4-hydroxyphenyl) diphenyl sulfone, 0.06mol of 4, 4' -difluorodiphenyl sulfone and 0.07mol of potassium carbonate into a three-neck flask in sequence, then adding 90mL of sulfolane and 35mL of toluene, slowly heating the system to 150 ℃ under the protection of argon, refluxing for 3 hours, discharging the toluene and the excess water, then adopting a gradient heating mode to raise the temperature to 200 ℃, reacting for 4 hours, obtaining a reaction product after the viscosity of the system is not changed any more, and washing the reaction product for multiple times by adopting deionized water and ethanol to obtain the white polyarylether sulfone modified material.
Example 3
Adding 0.05mol of 4,4 '-bis (4-hydroxyphenyl) diphenyl sulfone, 0.05mol of 4, 4' -difluorodiphenyl sulfone and 0.06mol of potassium carbonate into a three-neck flask in sequence, then adding 80mL of sulfolane and 25mL of toluene, slowly heating the system to 140 ℃ under the protection of argon, refluxing for 3 hours, discharging the toluene and the excess water, then adopting a gradient heating mode to raise the temperature to 200 ℃, reacting for 4 hours, obtaining a reaction product after the viscosity of the system is not changed any more, and washing the reaction product for multiple times by adopting deionized water and ethanol to obtain the white polyarylether sulfone modified material.
In the present invention, the properties of the modified materials of polyarylethersulfone prepared in examples 1 to 3 were analyzed, and the results are shown in the following table:
| example 1 | Example 2 | Example 3 | Control group | |
| Glass transition temperature (T)g) | 268 | 262 | 267 | 220 |
It should be noted that, in the comparison group in the table, the traditional polyarylethersulfone material polyphenylene sulfone resin (PPSU) is taken as an example for comparison, and it can be seen from the data in the table that, because a large amount of biphenyl groups are introduced into the polyarylethersulfone modified material prepared by the present invention, the glass transition temperature of the polyarylethersulfone modified material is greatly increased relative to the PPSU, thereby proving that the heat resistance of the polyarylethersulfone modified material prepared by the present invention is significantly improved.
Further, according to the modified polyarylethersulfone materials prepared in examples 1 to 3, the corresponding thin film materials are prepared, and the steps comprise: dissolving the polyarylethersulfone modified materials prepared in examples 1 to 3 and the control PPSU with an organic solvent, casting the dissolved solution on a clean glass plate, drying at 100 ℃ for 5 hours, and removing the solvent completely to obtain the corresponding film material.
The prepared film material was used for the detection of mechanical properties, and the results are as follows:
| example 1 | Example 2 | Example 3 | Control group | |
| Tensile Strength (MPa) | 72 | 74 | 71 | 60 |
| Tensile modulus (GPa) | 1.68 | 1.72 | 1.65 | 1.23 |
| Elongation at Break (%) | 22 | 19 | 21 | 35 |
As can be seen from the data in the table, the modified material of polyarylethersulfone prepared by the invention has better mechanical properties compared with PPSU, and can meet the requirements of high technical fields such as national defense and military industry, aerospace, electronic and electric appliances, medical treatment and health care on the thermal stability and mechanical strength of the polyarylethersulfone material.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (9)
1. A preparation method of a polyarylethersulfone modified material is characterized by comprising the following steps:
mixing 4,4 '-bis (4-hydroxyphenyl) diphenylsulfone, 4' -difluorodiphenylsulfone and a catalyst under an inert gas atmosphere, and then adding a dehydrating agent to obtain an intermediate mixture;
heating the intermediate mixture to 130-150 ℃, refluxing for 2-3h, heating to 180-200 ℃, and reacting for 4-5h to obtain the polyarylethersulfone modified material.
2. The method for preparing the modified material of polyarylethersulfone according to claim 1, wherein the mixing ratio of the 4,4 '-bis (4-hydroxyphenyl) diphenylsulfone, the 4, 4' -difluorodiphenylsulfone and the catalyst is 1:1:1.1-1.2 in terms of mole fraction.
3. The method for preparing polyarylethersulfone modified material of claim 1, wherein the catalyst is an alkali metal salt.
4. The method for preparing a modified material of polyarylethersulfone according to claim 1, wherein the dehydrating agent is a mixed solution of sulfolane and toluene.
5. The method for preparing modified material of polyarylethersulfone according to claim 1, wherein the dehydrating agent contains sulfolane 70-80% and toluene 20-30% by volume.
6. The method for preparing polyarylethersulfone modified material of claim 1, wherein the inert gas is one of nitrogen, argon and helium.
7. The method for preparing modified material of polyarylethersulfone as claimed in claim 1, wherein the step of heating the intermediate mixture to 130-150 ℃ and refluxing for 2-3h, and then raising the temperature gradient to 180-200 ℃ and reacting for 4-5h to obtain the modified material of polyarylethersulfone further comprises:
and repeatedly cleaning the polyarylethersulfone modified material by adopting an organic solvent and distilled water.
8. The method for preparing polyarylethersulfone modified material of claim 7, wherein the organic solvent is one of ethanol, diethyl ether and dichloromethane.
9. A modified material of polyarylethersulfone, characterized in that it is prepared by the method for preparing modified material of polyarylethersulfone as claimed in any of claims 1-8.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115058008A (en) * | 2022-07-22 | 2022-09-16 | 宁夏清研高分子新材料有限公司 | Polysulfone polymer and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3532670A (en) * | 1967-04-20 | 1970-10-06 | Bayer Ag | New,high-molecular,soluble,thermoplastic,modified polyphenyl ether-sulphons and process for the production tfereof |
| CN105295024A (en) * | 2015-11-24 | 2016-02-03 | 吉林大学 | Di(biphenyl) structure-containing polyethersulfones with high heat resistance class and preparation method thereof |
-
2021
- 2021-06-11 CN CN202110659937.XA patent/CN113388110A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3532670A (en) * | 1967-04-20 | 1970-10-06 | Bayer Ag | New,high-molecular,soluble,thermoplastic,modified polyphenyl ether-sulphons and process for the production tfereof |
| CN105295024A (en) * | 2015-11-24 | 2016-02-03 | 吉林大学 | Di(biphenyl) structure-containing polyethersulfones with high heat resistance class and preparation method thereof |
Non-Patent Citations (3)
| Title |
|---|
| XIN LIU ET AL.,: "Design and synthesis of poly(arylene ether sulfone)s with high glass transition temperature by introducing biphenylene groups", 《POLYMER INTERNATIONAL》 * |
| 刘一凡: "结晶型联苯聚芳醚砜的合成及性能研究", 《中国优秀博硕士学位论文全文数据库(硕士) 工程科技I辑》 * |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115058008A (en) * | 2022-07-22 | 2022-09-16 | 宁夏清研高分子新材料有限公司 | Polysulfone polymer and preparation method thereof |
| CN115058008B (en) * | 2022-07-22 | 2024-01-30 | 宁夏清研高分子新材料有限公司 | Polysulfone polymer and preparation method thereof |
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Application publication date: 20210914 |