CN111286194A - Wear-resistant self-lubricating polyimide resin and preparation method thereof - Google Patents
Wear-resistant self-lubricating polyimide resin and preparation method thereof Download PDFInfo
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- CN111286194A CN111286194A CN201911388288.3A CN201911388288A CN111286194A CN 111286194 A CN111286194 A CN 111286194A CN 201911388288 A CN201911388288 A CN 201911388288A CN 111286194 A CN111286194 A CN 111286194A
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- dianhydride
- polyimide resin
- resistant self
- diamine
- lubricating
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/04—Carbon
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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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
- C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/30—Sulfur-, selenium- or tellurium-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/30—Sulfur-, selenium- or tellurium-containing compounds
- C08K2003/3009—Sulfides
Abstract
The invention relates to a preparation method of wear-resistant self-lubricating polyimide resin, which comprises the steps of dissolving a diamine monomer in an organic solvent, adding dianhydride for reaction, adding a modified auxiliary agent into a PAA solution, preserving heat for a certain time, sequentially adding a dehydrating agent and a catalyst, heating for resin precipitation, cooling, centrifuging and drying to obtain the resin. The resin is subjected to compression molding, the friction coefficient of the plate is low, and the plate has a good wear-resistant self-lubricating effect.
Description
Technical Field
The invention belongs to the field of high polymer materials, and particularly relates to a wear-resistant self-lubricating polyimide resin and a preparation method thereof.
Background
Polyimide is a high-performance polymer containing an aromatic ring and an imide ring repeating unit structure, and has good mechanical property and thermal stability. With the development of decades, polyimide has been developed into a kind of high performance materials with complete variety and various products, and is always the key point of research and development in various countries. Particularly, the material has excellent thermal oxidation resistance stability, outstanding mechanical property at high temperature, radiation resistance, good chemical and physical stability and the like, and is widely applied to the fields of aerospace, weaponry, automobiles, electronic appliances and the like.
In recent years, polyimide is widely applied to high-temperature bearings and fasteners, and is required to have a good wear-resistant self-lubricating effect, and a polyimide resin body has a certain wear-resistant self-lubricating effect, but with the difference of application environments, increasingly strict requirements are provided for the wear resistance of polyimide. In the literature, graphite, polytetrafluoroethylene, glass fiber and the like are added into polyimide for compounding so as to achieve the purpose of improving the wear resistance of the polyimide, and although the wear resistance of the material can be improved, the mechanical property of the material is often influenced to a certain extent due to the large addition amount.
The patent application number 201910826973.3 discloses a method for improving the lubricating property of a multi-walled carbon nanotube/polyimide high-lubricity composite material by adding multi-walled carbon nanotubes in situ in a polyimide monomer, but the addition amount of the multi-walled carbon nanotubes is low (less than 2%), a polyamic acid solution is imidized by adopting a thermal imidization method, and the obtained product is cured into a film. However, the addition of a filler with a larger amount in the synthesis stage of polyamic acid may adversely affect the synthesis process of polyamic acid, and the use of a film-like product produced by thermal imidization may limit the processing, which is not favorable for the popularization and utilization of the product.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a preparation method of wear-resistant self-lubricating polyimide resin. According to the method, the auxiliary agent with a certain particle size is screened and added into the unseparated PAA solution, so that the polyimide can be induced to separate out uniform powder with a fine particle size, meanwhile, the polyimide resin and the auxiliary agent can be mutually wrapped and mixed more uniformly to form better modified resin powder, the fact that a small amount of the auxiliary agent is used to achieve higher wear resistance is unexpectedly found, the mechanical property can be improved, the dispersing auxiliary agent does not need to be added, and the adverse effect caused by the addition of a large amount of the dispersing auxiliary agent is avoided.
The technical scheme adopted by the invention is as follows:
a preparation method of wear-resistant self-lubricating polyimide resin comprises the following steps:
s1: dissolving a diamine monomer in an organic solvent, and then adding dianhydride in batches for reaction to obtain a polyamic acid solution;
s2: adding a modification auxiliary agent into the polyamic acid solution;
s3: adding a dehydrating agent and a catalyst, and heating to separate out resin;
further, the reaction temperature in S1 is preferably 0 to 30 ℃.
Further, the organic solvent in S1 is preferably one or more of dimethylacetamide (DMAc), Dimethylformamide (DMF), Dimethylsulfoxide (DMSO), and N-methylpyrrolidone (NMP).
Further, the mass of the organic solvent is 3 to 6 times of the total mass of the diamine and the dianhydride, and more preferably, the mass of the organic solvent is 3.5 to 4.5 times of the total mass of the diamine and the dianhydride.
Further, the diamine monomer in S1 is preferably one or more of 3,4 '-diaminodiphenyl ether, 4' -diaminodiphenyl ether, 3,4 '-diaminodiphenyl sulfone, 4' -diaminodiphenyl sulfone, m-phenylenediamine, p-phenylenediamine, and biphenyldiamine.
Further, the dianhydride monomer in S1 is preferably one or more of pyromellitic dianhydride, 3 ', 4,4 ' -biphenyl tetracarboxylic dianhydride, 3 ', 4,4 ' -benzophenone tetracarboxylic dianhydride, and 4,4 ' -biphenyl ether dianhydride.
Further, the molar ratio of the dianhydride to the diamine is (1-1.5): 1.
Further, the dianhydride is added in multiple portions.
Further preferably, the addition is carried out in 6 portions.
Further, the modification assistant is added into S2 and then the temperature is kept for a period of time.
Further, the heat preservation time is preferably 2-4 h.
Further, the modification auxiliary agent is preferably one or more of graphite, molybdenum disulfide and polytetrafluoroethylene.
Furthermore, the particle size D90 of the modification auxiliary agent is 10-20 μm.
Furthermore, the total mass ratio of the modification auxiliary agent to the diamine and the dianhydride is 1 (4-8).
The dehydrating agent in S3 is one or two of acetic anhydride and propionic anhydride.
The catalyst in S3 is one or two of triethylamine and pyridine.
The mass of the dehydrating agent is 1-5 times of the total mass of diamine and dianhydride.
The mass of the catalyst is 2-5% of the total mass of diamine and dianhydride.
Further, the heating in the step of S3 is heating to 80-100 ℃.
Further, S4 is further included after S3, and the resin is obtained through cooling, centrifugation and drying.
Further, the drying temperature is 180-230 ℃.
Adding the resin powder into a flat vulcanizing machine for compression molding, wherein the compression molding temperature is as follows: 340-390 ℃, pressure: 30-100MPa, time: 5-15 min; and (3) carrying out friction coefficient test and mechanical property test on the obtained polyimide plate.
The polyimide is molded, the tested friction coefficient is less than or equal to 0.1, the tensile strength is more than or equal to 100MPa, the bending strength is more than or equal to 140MPa, and the impact strength is more than or equal to 200kJ/m 2.
The invention has the advantages that the modification auxiliary agent with a certain particle size is added into the PAA solution to induce the polyimide resin to separate out powder with the same particle size and uniformity, the wear resistance of the resin body can be improved by using a small amount of modification auxiliary agent, and the integral mechanical property can also be improved.
Detailed Description
The present invention will be described in detail with reference to specific examples. The following examples will assist those skilled in the art in further understanding the invention, but are not intended to limit the invention in any way. It should be noted that variations and modifications can be made by persons skilled in the art without departing from the spirit of the invention. All falling within the scope of the present invention. The tensile strength of the invention is tested according to GB/T1040.2-2006, the bending strength is tested according to GB/T9341-2008, and the impact strength is tested according to GB/T1043.1-2008.
The preparation method of the polyimide resin comprises the following steps:
dissolving a diamine monomer in an organic solvent at normal temperature, adding dianhydride in batches for reaction, adding a modified auxiliary agent into a PAA solution, preserving heat for a certain time, sequentially adding a dehydrating agent and a catalyst, heating for resin precipitation, cooling, centrifuging and drying to obtain resin; adding the resin powder into a flat vulcanizing machine for compression molding, wherein the compression molding temperature is as follows: 340-390 ℃, pressure: 30-100MPa, time: 5-15 min; and (3) carrying out friction coefficient test and mechanical property test on the obtained polyimide plate.
The invention is further illustrated by the following examples:
example 1:
dissolving 20g of 4,4 '-diaminodiphenyl ether in 167.32g of DMAc at normal temperature, adding 32g of 4, 4' -diphenyl ether dianhydride in six batches, stirring for reacting for 2 hours, then adding 7g of graphite, preserving heat for 3 hours, adding 104g of acetic anhydride and 1.04g of triethylamine, heating to 90 ℃, stirring for reacting for 2 hours, then cooling to room temperature, centrifuging, and drying at 200 ℃ for 4 hours to obtain uniform resin powder.
Example 2:
dissolving 20g of 4,4 '-diaminodiphenyl ether in 167.32g of NMP at normal temperature, adding 32g of 4, 4' -diphenyl ether dianhydride in six batches, stirring for reacting for 2 hours, then adding 7g of graphite, preserving heat for 3 hours, adding 104g of acetic anhydride and 1.04g of triethylamine, heating to 90 ℃, stirring for reacting for 2 hours, then cooling to room temperature, centrifuging, and drying at 230 ℃ for 4 hours to obtain uniform resin powder.
Example 3:
dissolving 20g of 4,4 '-diaminodiphenyl ether in 167.32g of DMAc at normal temperature, adding 32g of 4, 4' -diphenyl ether dianhydride in six batches, stirring for reacting for 2 hours, then adding 7g of molybdenum disulfide, preserving heat for 3 hours, adding 104g of acetic anhydride and 1.04g of triethylamine, heating to 90 ℃, stirring for reacting for 2 hours, then cooling to room temperature, centrifuging, and drying at 200 ℃ for 4 hours to obtain uniform resin powder.
Example 4:
dissolving 20g of 4,4 '-diaminodiphenyl ether in 167.32g of NMP at normal temperature, adding 32g of 4, 4' -diphenyl ether dianhydride in six batches, stirring for reacting for 2 hours, then adding 7g of molybdenum disulfide, preserving heat for 3 hours, adding 104g of acetic anhydride and 1.04g of triethylamine, heating to 90 ℃, stirring for reacting for 2 hours, then cooling to room temperature, centrifuging, and drying at 230 ℃ for 4 hours to obtain uniform resin powder.
Comparative example 1:
adding 20g of 4,4 '-diaminodiphenyl ether and 7g of graphite into 167.32g of DMAc at normal temperature, adding 32g of 4, 4' -diphenyl ether dianhydride in six batches, stirring for reacting for 5 hours, adding 104g of acetic anhydride and 1.04g of triethylamine, heating to 90 ℃, stirring for reacting for 2 hours, then cooling to room temperature, centrifuging, and drying at 200 ℃ for 4 hours to obtain uniform resin powder.
Comparative example 2:
dissolving 20g of 4,4 '-diaminodiphenyl ether in 167.32g of NMP at normal temperature, adding 32g of 4, 4' -diphenyl ether dianhydride in six batches, stirring for reaction for 5 hours, adding 104g of acetic anhydride and 1.04g of triethylamine, heating to 90 ℃, stirring for reaction for 2 hours, cooling to room temperature, centrifuging, and drying at 200 ℃ for 4 hours to obtain uniform resin powder.
Comparative example 3:
dissolving 20g of 4,4 '-diaminodiphenyl ether in 167.32g of DMAc at normal temperature, adding 32g of 4, 4' -diphenyl ether dianhydride in six batches, stirring for reacting for 5 hours, adding 104g of acetic anhydride and 1.04g of triethylamine, heating to 80 ℃, stirring for reacting for 2 hours, then cooling to room temperature, centrifuging, and drying at 200 ℃ for 4 hours to obtain uniform resin powder.
Comparative example 4
Dissolving 20g of 4,4 '-diaminodiphenyl ether in 167.32g of DMAc at normal temperature, adding 32g of 4, 4' -diphenyl ether dianhydride in six batches, stirring for reacting for 5 hours, adding 104g of acetic anhydride and 1.04g of triethylamine, heating to 100 ℃, stirring for reacting for 2 hours, then cooling to room temperature, centrifuging, and drying at 200 ℃ for 4 hours to obtain uniform resin powder.
The resin powders of the above examples and comparative examples were put into a press vulcanizer to be press-molded, and the press-molding temperature: 340-390 ℃, pressure: 30-100MPa, time: 5-15 min; and (3) carrying out friction coefficient test and mechanical property test on the obtained polyimide plate. The properties are compared in the following table:
compared with the resin obtained by the method, the wear resistance of the resin body is improved, and the mechanical property is integrally improved.
Claims (10)
1. A preparation method of wear-resistant self-lubricating polyimide resin is characterized by comprising the following steps:
s1: dissolving a diamine monomer in an organic solvent, and then adding dianhydride in batches for reaction to obtain a polyamic acid solution;
s2: adding a modification auxiliary agent into the polyamic acid solution;
s3: adding a dehydrating agent and a catalyst, and heating to separate out resin;
the reaction temperature in S1 is preferably 0 to 30 ℃.
2. The method for preparing the abrasion-resistant self-lubricating polyimide resin according to claim 1, wherein the organic solvent in S1 is one or more of dimethylacetamide, dimethylformamide, dimethyl sulfoxide and N methyl pyrrolidone, and the mass of the organic solvent is 3-6 times of the total mass of diamine and dianhydride.
3. The method for preparing the abrasion-resistant self-lubricating polyimide resin according to claim 1, wherein the mass of the organic solvent is 3.5 to 4.5 times of the total mass of the diamine and the dianhydride.
4. The method for preparing the abrasion-resistant self-lubricating polyimide resin according to claim 1, wherein: the diamine monomer in S1 is one or more of 3,4 '-diaminodiphenyl ether, 4' -diaminodiphenyl ether, 3,4 '-diaminodiphenyl sulfone, 4' -diaminodiphenyl sulfone, m-phenylenediamine, p-phenylenediamine and biphenyldiamine;
the dianhydride monomer in S1 is one or more of pyromellitic dianhydride, 3 ', 4,4 ' -biphenyl tetracarboxylic dianhydride, 3 ', 4,4 ' -benzophenone tetracarboxylic dianhydride and 4,4 ' -biphenyl ether dianhydride.
5. The method for preparing the abrasion-resistant self-lubricating polyimide resin according to claim 1, wherein: the modified auxiliary agent is one or more of graphite, molybdenum disulfide and polytetrafluoroethylene.
6. The method for preparing the abrasion-resistant self-lubricating polyimide resin according to claim 1, wherein: the molar ratio of the dianhydride to the diamine is (1-1.5):1, and the dianhydride is added for multiple times.
7. The preparation method of the wear-resistant self-lubricating polyimide resin as claimed in claim 1, wherein the heat preservation time is 2-4h after the modification auxiliary is added into S2, and the particle size of the modification auxiliary is 10-20 μm.
8. The preparation method of the abrasion-resistant self-lubricating polyimide resin as claimed in claim 1, wherein the total mass ratio of the modification auxiliary agent to the diamine and the dianhydride is 1 (4-8).
9. The method for preparing the abrasion-resistant self-lubricating polyimide resin according to claim 1, wherein the dehydrating agent in S3 is one or two of acetic anhydride and propionic anhydride, the catalyst in S3 is one or two of triethylamine and pyridine, the mass of the dehydrating agent is 1-5 times of the total mass of diamine and dianhydride, the mass of the catalyst is 2-5% of the total mass of diamine and dianhydride, and the heating in the S3 step is to 80-100 ℃.
10. A polyimide resin produced by the method according to any one of claims 1 to 9.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112062959A (en) * | 2020-08-24 | 2020-12-11 | 长沙新材料产业研究院有限公司 | Glass fiber modified polyimide resin and preparation method thereof |
| CN112126228A (en) * | 2020-08-24 | 2020-12-25 | 长沙新材料产业研究院有限公司 | Glass fiber reinforced polyimide composite material and preparation method thereof |
| CN112795186A (en) * | 2020-12-25 | 2021-05-14 | 长沙新材料产业研究院有限公司 | Modified polyimide resin and preparation method thereof |
| CN113307972A (en) * | 2021-06-15 | 2021-08-27 | 中国科学院长春应用化学研究所 | Polyimide and preparation method thereof, and polyimide sealing ring and preparation method thereof |
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| CN106905528A (en) * | 2017-04-13 | 2017-06-30 | 中国科学院长春应用化学研究所 | A kind of polyimide resin, its preparation method and composite polyimide material |
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| CN1215741A (en) * | 1997-10-23 | 1999-05-05 | 上海市合成树脂研究所 | Potassium titanate crystal whisker reinforced polyimide composite material |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112062959A (en) * | 2020-08-24 | 2020-12-11 | 长沙新材料产业研究院有限公司 | Glass fiber modified polyimide resin and preparation method thereof |
| CN112126228A (en) * | 2020-08-24 | 2020-12-25 | 长沙新材料产业研究院有限公司 | Glass fiber reinforced polyimide composite material and preparation method thereof |
| CN112795186A (en) * | 2020-12-25 | 2021-05-14 | 长沙新材料产业研究院有限公司 | Modified polyimide resin and preparation method thereof |
| CN113307972A (en) * | 2021-06-15 | 2021-08-27 | 中国科学院长春应用化学研究所 | Polyimide and preparation method thereof, and polyimide sealing ring and preparation method thereof |
| CN113307972B (en) * | 2021-06-15 | 2022-06-07 | 中国科学院长春应用化学研究所 | Polyimide and preparation method thereof, and polyimide sealing ring and preparation method thereof |
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Application publication date: 20200616 |