CN110684353A - High-performance friction material and application thereof - Google Patents
High-performance friction material and application thereof Download PDFInfo
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- 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
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/24—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
- C07C67/26—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane ring
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/27—Condensation of epihalohydrins or halohydrins with compounds containing active hydrogen atoms
- C07D301/28—Condensation of epihalohydrins or halohydrins with compounds containing active hydrogen atoms by reaction with hydroxyl radicals
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- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
- C07D303/23—Oxiranylmethyl ethers of compounds having one hydroxy group bound to a six-membered aromatic ring, the oxiranylmethyl radical not being further substituted, i.e.
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
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- C08K2003/2227—Oxides; Hydroxides of metals of aluminium
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/32—Phosphorus-containing compounds
- C08K2003/321—Phosphates
- C08K2003/327—Aluminium phosphate
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/12—Shape memory
Abstract
The invention discloses a high-performance friction material and application thereof. The preparation method comprises the following steps of blending 2-allyl phenyl glycidyl ether and terephthalic acid in acetonitrile, and carrying out esterification reaction under the condition that quaternary ammonium salt is used as a catalyst to obtain bis (3- (2-allyl phenoxy) -2-hydroxypropyl) terephthalate containing reversible dynamic groups; then evenly mixing bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate with bismaleimide, aluminum phosphate and aluminum oxide, and curing to obtain the high-performance friction material. The high-performance friction material prepared by the invention not only has good wear resistance, heat resistance and flame retardance, but also can realize remolding under the condition of hot pressing, and has wide application prospect.
Description
Technical Field
The invention relates to a high-performance friction material and preparation and remodeling methods thereof, belonging to the field of thermosetting shape memory polymers and recyclable polymers.
Background
The thermosetting resin is considered to be formed once and cannot be recycled, once the wear-resistant product has defects such as cracks, the wear-resistant product can only be scrapped, and serious resource waste and environmental pollution can be caused. Recently, remoldable thermoset SMPs have not been developed that combine high heat resistance, flame retardant properties and good shape memory properties and are not suitable for use as wear resistant materials. The Oxygen Index (OI) is the minimum oxygen concentration required for the material to undergo flaming combustion in a flow of oxygen-nitrogen mixture under specified conditions. Expressed as a volume percentage of oxygen; a high oxygen index means that the material is not readily combustible, a low oxygen index means that the material is readily combustible, and a flame retardancy is considered to be difficult if the material cannot be combusted in ordinary air at an oxygen index of 26 or more.
In addition, bismaleimide is a thermosetting resin, has excellent mechanical properties and heat resistance, is widely applied to the fields of aerospace and the like, and at present, wear-resistant materials based on bismaleimide resin are rarely reported, most of the bismaleimide resin is used as a modifier (the dosage is less than that of the main resin) for modifying other substances, and the bismaleimide resin prepared by adopting a reasonable process has good practical significance.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides a remodelable shape memory bismaleimide resin with good shape memory performance, high heat resistance and high tensile property and a preparation method thereof.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
a high-performance friction material is prepared by a method comprising the following steps:
(1) reacting 2-allylphenyl glycidyl ether with terephthalic acid in the presence of quaternary ammonium salt to prepare bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate;
(2) stirring and mixing bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate, bismaleimide, a zinc compound and a filler system to obtain a high-performance friction material system; the filler system comprises epoxy resin, aluminum phosphate and aluminum oxide;
(3) and carrying out hot-pressing curing and post-treatment on the high-performance friction material system to obtain the high-performance friction material.
The invention also discloses a remodeling method of the shape memory bismaleimide resin, which comprises the following steps:
(1) reacting 2-allylphenyl glycidyl ether with terephthalic acid in the presence of quaternary ammonium salt to prepare bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate;
(2) stirring and mixing bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate, bismaleimide, a zinc compound and a filler system to obtain a high-performance friction material system; the filler system comprises epoxy resin, aluminum phosphate and aluminum oxide;
(3) carrying out hot-pressing curing and post-treatment on the high-performance friction material system to obtain the high-performance friction material;
(4) and (3) carrying out hot pressing treatment on the cracked high-performance friction material to obtain a repaired wear-resistant material, thereby realizing self repair of the high-performance friction material.
Adding epoxy resin into ethanol containing aluminum oxide and aluminum phosphate, stirring for 5 hours, and drying to obtain a filler system; the mass ratio of the aluminum oxide to the aluminum phosphate is 1: 0.45; the epoxy resin is bisphenol A epoxy resin; the particle size of the alumina is 0.3-0.4 micron; the particle size of the aluminum phosphate is 0.3-0.4 microns. Preferably, the mass of the epoxy resin is 10% of the mass sum of the alumina and the aluminum phosphate.
In the invention, epoxy chloropropane is added into a mixed solution of 2-allyl phenol, sodium hydroxide, quaternary ammonium salt and tetrahydrofuran to react to prepare 2-allyl phenyl glycidyl ether.
In the technical scheme, in the step (1), the mass ratio of the 2-allyl phenyl glycidyl ether to the terephthalic acid to the quaternary ammonium salt is 120: 40-50: 5-10, the reaction temperature is 65-80 ℃, and the reaction time is 8-12 hours; in the step (2), the mass ratio of bismaleimide, bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate, zinc compound and filler system is 50: 75-80: 6-6.5: 5.5, the stirring temperature is 130-135 ℃, and the stirring time is 80-100 min; in the step (3), the hot pressing temperature is 150-220 ℃, the pressure is 1-5 MPa, the time is 3-6 h, the post-treatment temperature is 240 ℃, and the time is 2 h.
In the technical scheme, the quaternary ammonium salt is tetramethyl ammonium bromide and/or tetrabutyl ammonium bromide; the zinc compound is zinc acetylacetonate hydrate; the bismaleimide is one or more of N, N '-4,4' -diphenylmethane bismaleimide, N '- (1, 4-phenylene) bismaleimide and N, N' -m-phenylene bismaleimide.
The invention also discloses application of the high-performance friction material in preparing wear-resistant materials.
In the technical scheme, in the step (4), the temperature of the hot-pressing treatment is 260-280 ℃, the pressure is 30-35 MPa, and the time is 4-6 h.
Compared with the prior art, the invention has the beneficial effects that:
1. the invention synthesizes a novel diallyl compound containing reversible dynamic groups, which is used for modifying bismaleimide and preparing a novel high-performance friction material containing reversible covalent bonds.
2. Compared with the traditional thermosetting SMPs, the remodelable shape memory bismaleimide prepared by the invention has good shape memory performance and remodeling performance.
3. Compared with the remoldable shape memory thermosetting resin reported in the existing literature, the high-performance friction material prepared by the invention has outstanding heat resistance, and the good heat resistance of the high-performance friction material is benefited by reasonable formula and preparation process of a resin system and a large number of benzene rings in the resin and six-membered ring and other ring structures formed by curing; especially an oxygen index exceeding 26.
4. Compared with the traditional 2,2' -diallyl bisphenol A, the synthesis of the novel diallyl compound-bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate provided by the invention does not need high-temperature rearrangement, and has the advantages of simple synthesis process and low energy consumption.
5. Compared with the traditional 2,2' -diallyl bisphenol A, the bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate synthesized by the method is non-bisphenol A type, so that the risks of carcinogenesis, teratogenicity, influence on fertility and the like of the bisphenol A are avoided.
Drawings
FIG. 1 is a reaction scheme for synthesizing 2-allylphenyl glycidyl ether and bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate prepared according to the present invention.
FIG. 2 shows the NMR spectrum of 2-allylphenyl glycidyl ether prepared in example 1 of the present invention: (1H-NMR）。
FIG. 3 is a drawing showing bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate prepared in example 1 of the present invention1H-NMR。
FIG. 4 is a NMR spectrum of bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate prepared in example 1 of the present invention (C13C-NMR）。
FIG. 5 is a high resolution mass spectrum of bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate prepared in example 1 of the present invention.
Detailed Description
The technical solution of the present invention is further described with reference to the accompanying drawings and examples.
The preparation method of the high-performance friction material comprises the following steps:
(1) reacting 2-allylphenyl glycidyl ether with terephthalic acid in the presence of quaternary ammonium salt to prepare bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate;
(2) stirring and mixing bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate, bismaleimide, a zinc compound and a filler system to obtain a high-performance friction material system; the filler system comprises epoxy resin, aluminum phosphate and aluminum oxide;
(3) and carrying out hot-pressing curing and post-treatment on the high-performance friction material system to obtain the high-performance friction material.
Synthesis example
Mixing 120g of 2-allylphenol, 140g of sodium hydroxide, 10g of tetrabutylammonium bromide and 230g of tetrahydrofuran by mass, and carrying out heat preservation reaction for 1.5h at 35 ℃ under the stirring condition to obtain a solution A; slowly dropwise adding 270g of epoxy chloropropane into the solution A, and keeping the temperature at 35 ℃ and stirring for reacting for 6 hours; and after the reaction is finished, removing tetrahydrofuran and epichlorohydrin by vacuum rotary evaporation to obtain a crude product. Washing the crude product with saturated ammonium chloride solution (200 mL × 2) and deionized water (200 mL × 2), and separating and purifying with chromatographic column to obtain yellow transparent liquid, i.e. 2-allyl phenyl glycidyl ether, with yield of about 93%, according to the reaction formula1H-NMR is shown in the attached figures 1 and 2 respectively. Mixing 120g of 2-allyl phenyl glycidyl ether, 45g of terephthalic acid, 10g of tetrabutylammonium bromide and 230g of acetonitrile by mass, and carrying out heat preservation reaction for 8 hours at 70 ℃ under the stirring condition; after the reaction is finished, removing acetonitrile by vacuum rotary evaporation to obtain a crude product. Washing the crude product with saturated sodium bicarbonate solution (200 mL × 2) and deionized water (200 mL × 2), and separating and purifying with chromatographic column to obtain yellow transparent viscous liquid, i.e. bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate with yield of 86%, according to the reaction formula,1H-NMR、13C-NMR and high resolution mass spectra are shown in FIGS. 1, 3, 4 and 5, respectively, for the following examples.
14.5g of epoxy resin (Sanmu SM 6101) was added to 800g of ethanol containing 100g of alumina (particle size 350 nm) and 45g of aluminum phosphate (particle size 350 nm), stirred at room temperature (1200 rpm) for 5 hours and then baked at 80 ℃ for 1 hour to obtain a filler system consisting of epoxy resin, aluminum phosphate and alumina, which was used in the following examples and comparative example one.
EXAMPLE preparation of high Performance Friction Material
Mixing 50g of N, N '-4,4' -diphenylmethane bismaleimide, 76.17g of bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate, 6.29g (22.3 mmol) of zinc acetylacetonate hydrate and 5.5g of a filler system, stirring at 130 ℃, and carrying out prepolymerization for 90min to obtain a prepolymer, and sampling to test DSC; cooling the clear prepolymer to room temperature, adding the cooled clear prepolymer into a mold preheated at 150 ℃, and carrying out hot pressing and post-treatment according to the following processes: 150 ℃/1 h/1MPa +180 ℃/2 h/3MPa +200 ℃/1.5 h/5MPa +220 ℃/1.5 h/5MPa and 240 ℃/2 h; and (5) naturally cooling and demoulding to obtain the high-performance friction material, and testing TG, DMA, oxygen index and wear resistance.
EXAMPLE two self-repairing method of high-Performance Friction Material and self-repaired wear-resistant Material
The wear-resistant material of the first embodiment is cracked (stainless steel is hammered and irregularly split into three pieces), then is placed into a preheated die at 200 ℃ (the cracks are in contact with each other), and then is hot-pressed for 5 hours under the conditions that the temperature is 270 ℃ and the pressure is 30 MPa; and demolding after natural cooling to obtain the self-repairing wear-resistant material, thereby realizing the self-repairing of the bismaleimide wear-resistant material. The obtained self-repairing wear-resistant material has smooth and crack-free surface, which indicates that the resin particles have dynamic ester exchange reaction to reconnect the particles. This result is a good demonstration of the remodeling that can be achieved by the shape memory bismaleimide resin prepared by the present invention. And testing the TG, the oxygen index and the wear resistance of the self-repairing wear-resistant material.
Comparative example 1
1) Preparation of diallyl bisphenol A modified bismaleimide resin
Stirring 50g of N, N ' -4,4' -diphenylmethane bismaleimide, 43.03g of 2,2' -diallyl bisphenol A, 6.29g of zinc acetylacetonate hydrate and 4g of a filler system at 130 ℃ for prepolymerization for 60min to obtain a prepolymer, and sampling to test DSC; cooling the clear prepolymer to room temperature, adding the cooled clear prepolymer into a mold preheated at 150 ℃, and carrying out hot pressing and post-treatment according to the following processes: 150 ℃/1 h/1MPa +180 ℃/2 h/3MPa +200 ℃/1.5 h/5MPa +220 ℃/1.5 h/5MPa and 240 ℃/2 h; and (5) naturally cooling and then demoulding to obtain the wear-resistant material, and testing the wear resistance. Wherein 10g of epoxy resin (Sanmu SM 6101) was added to 500g of ethanol containing 100g of alumina (particle size 350 nm), stirred at room temperature (800 rpm) for 2 hours, and then baked at 80 ℃ for 1 hour to obtain a filler system, which was used in comparative example one.
The wear-resistant material in the first comparative example is cracked (the stainless steel is hammered and irregularly cracked into five blocks), then is placed into a preheated die at 200 ℃ (the cracks are contacted), and then is hot-pressed for 5 hours under the conditions that the temperature is 270 ℃ and the pressure is 30 MPa; and (3) naturally cooling and demoulding to obtain a plate with obvious cracks, wherein the plate is easy to break and almost has no mechanical strength, and the diallyl bisphenol A modified bismaleimide resin is proved not to be remodelable.
From the DSC results (10 ℃/min) of the prepolymer of the high-performance friction material of the example of the present invention and the prepolymer of the diallyl bisphenol a modified bismaleimide resin of the comparative example i under a nitrogen atmosphere, it can be seen that the maximum exothermic peak of the reaction of the prepolymer of the high-performance friction material of the example is 244.1 ℃ which is lower than 250.3 ℃ of the diallyl bisphenol a modified bismaleimide resin, indicating that the reactivity of the prepolymer of the high-performance friction material of the example is higher than that of the diallyl bisphenol a modified bismaleimide resin.
Wherein, TdiTo initiate the thermal decomposition temperature, it was routinely obtained according to the TGA curve (10 ℃/min) of the sample under nitrogen atmosphere; t isgThe glass transition temperature is obtained by DMA test (1 Hz, 3 ℃/min, 20-350 ℃, three-point bending); the oxygen index is tested according to GBT 24093.
Comparative example No. two
Mixing 50g of N, N '-4,4' -diphenylmethane bismaleimide, 76.17g of bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate and 6.29g of zinc acetylacetonate hydrate, and stirring at 130 ℃ to perform prepolymerization for 60min to obtain a prepolymer; cooling the clear prepolymer to room temperature, adding the cooled clear prepolymer into a mold preheated at 150 ℃, and carrying out hot pressing and post-treatment according to the following processes: 150 ℃/1 h/1MPa +180 ℃/2 h/3MPa +200 ℃/1.5 h/5MPa +220 ℃/1.5 h/5MPa and 240 ℃/2 h; and (5) naturally cooling and demoulding to obtain the high-performance friction material, and testing TG, oxygen index and wear resistance.
Comparative example No. three
Mixing 50g of N, N '-4,4' -diphenylmethane bismaleimide, 76.17g of bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate, 6.29g of zinc acetylacetonate hydrate and 5.5g of a filler system, and stirring at 130 ℃ to perform prepolymerization for 90min to obtain a prepolymer; cooling the clear prepolymer to room temperature, adding the cooled clear prepolymer into a mold preheated at 150 ℃, and carrying out hot pressing and post-treatment according to the following processes: 150 ℃/1 h/1MPa +180 ℃/2 h/3MPa +200 ℃/1.5 h/5MPa +220 ℃/1.5 h/5MPa and 240 ℃/2 h; and (5) naturally cooling and demoulding to obtain the high-performance friction material, and testing TG and wear resistance. In comparative example, 1.45gKH-550 (2 wt%) was added to 400g of ethanol containing 50g of alumina (particle size 350 nm) and 22.5g of aluminum phosphate (particle size 350 nm), stirred at room temperature (1200 rpm) for 5 hours, and then baked at 80 ℃ for 1 hour to obtain a filler system.
Table 1 shows the above examples and the related performance tests of comparative examples, and it can be seen that the aluminum oxide/phosphate composited with epoxy resin, together with bismaleimide, can exhibit excellent wear resistance while ensuring heat resistance.
Claims (10)
1. A high-performance friction material is characterized in that the preparation method of the high-performance friction material comprises the following steps:
(1) reacting 2-allylphenyl glycidyl ether with terephthalic acid in the presence of quaternary ammonium salt to prepare bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate;
(2) stirring and mixing bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate, bismaleimide, a zinc compound and a filler system to obtain a high-performance friction material system; the filler system comprises epoxy resin, aluminum phosphate and aluminum oxide;
(3) and carrying out hot-pressing curing and post-treatment on the high-performance friction material system to obtain the high-performance friction material.
2. The high-performance friction material of claim 1, wherein 2-allyl phenyl glycidyl ether is prepared by adding epoxy chloropropane to a mixture of 2-allyl phenol, sodium hydroxide, quaternary ammonium salt and tetrahydrofuran, and reacting.
3. The high-performance friction material as claimed in claim 1, wherein in the step (1), the mass ratio of the 2-allyl phenyl glycidyl ether to the terephthalic acid to the quaternary ammonium salt is 120: 40-50: 5-10, the reaction temperature is 65-80 ℃, and the reaction time is 8-12 h; in the step (2), the mass ratio of bismaleimide, bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate, zinc compound and filler system is 50: 75-80: 6-6.5: 5.5, the stirring temperature is 130-135 ℃, and the stirring time is 80-100 min; in the step (3), the hot pressing temperature is 150-220 ℃, the pressure is 1-5 MPa, the time is 3-6 h, the post-treatment temperature is 240 ℃, and the time is 2 h.
4. The high performance friction material of claim 1, wherein the quaternary ammonium salt is tetramethylammonium bromide and/or tetrabutylammonium bromide; the zinc compound is zinc acetylacetonate hydrate; the bismaleimide is one or more of N, N '-4,4' -diphenylmethane bismaleimide, N '- (1, 4-phenylene) bismaleimide and N, N' -m-phenylene bismaleimide; the epoxy resin is bisphenol A epoxy resin; the particle size of the alumina is 0.3-0.4 micron; the particle size of the aluminum phosphate is 0.3-0.4 microns.
5. The high-performance friction material as claimed in claim 1, wherein the epoxy resin is added into ethanol containing alumina and aluminum phosphate, stirred for 5 hours and then dried to obtain a filler system; the mass ratio of the aluminum oxide to the aluminum phosphate is 1: 0.45.
6. A self-repairing method of a high-performance friction material is characterized by comprising the following steps:
(1) reacting 2-allylphenyl glycidyl ether with terephthalic acid in the presence of quaternary ammonium salt to prepare bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate;
(2) stirring and mixing bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate, bismaleimide, a zinc compound and a filler system to obtain a high-performance friction material system; the filler system comprises epoxy resin, aluminum phosphate and aluminum oxide;
(3) carrying out hot-pressing curing and post-treatment on the high-performance friction material system to obtain a high-performance friction material;
(4) and (3) carrying out hot pressing treatment on the cracked high-performance friction material to obtain a repaired wear-resistant material, thereby realizing self repair of the high-performance friction material.
7. The self-repairing method of the high-performance friction material according to claim 6, wherein in the step (1), the mass ratio of the 2-allyl phenyl glycidyl ether to the terephthalic acid to the quaternary ammonium salt is 120: 40-50: 5-10, the reaction temperature is 65-80 ℃, and the reaction time is 8-12 hours; in the step (2), the mass ratio of bismaleimide, bis (3- (2-allylphenoxy) -2-hydroxypropyl) terephthalate, zinc compound and filler system is 50: 75-80: 6-6.5: 5.5, the stirring temperature is 130-135 ℃, and the stirring time is 80-100 min; in the step (3), the hot pressing temperature is 150-220 ℃, the pressure is 1-5 MPa, the time is 3-6 h, the post-treatment temperature is 240 ℃, and the time is 2 h; in the step (4), the temperature of the hot pressing treatment is 260-280 ℃, the pressure is 30-35 MPa, and the time is 4-6 h.
8. The self-repairing method of the high-performance friction material of claim 6, wherein the quaternary ammonium salt is tetramethylammonium bromide and/or tetrabutylammonium bromide; the zinc compound is zinc acetylacetonate hydrate; the bismaleimide is one or more of N, N '-4,4' -diphenylmethane bismaleimide, N '- (1, 4-phenylene) bismaleimide and N, N' -m-phenylene bismaleimide.
9. The self-repairing method of the high-performance friction material of claim 6, wherein the filler system is obtained by adding epoxy resin into ethanol containing alumina and aluminum phosphate, stirring for 5 hours, and then drying; the mass ratio of the aluminum oxide to the aluminum phosphate is 1: 0.45; the epoxy resin is bisphenol A epoxy resin; the particle size of the alumina is 0.3-0.4 micron; the particle size of the aluminum phosphate is 0.3-0.4 microns.
10. Use of the high performance friction material of claim 1 in the manufacture of an abrasion resistant article.
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| CN105418923A (en) * | 2016-01-23 | 2016-03-23 | 苏州大学 | Modified bismaleimide resin and preparation method thereof |
| CN106700073A (en) * | 2016-12-03 | 2017-05-24 | 苏州大学 | Modified bismaleimide resin and preparation method thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115053078A (en) * | 2020-04-02 | 2022-09-13 | 舍弗勒技术股份两合公司 | Wet friction material with quaternary ammonium salt |
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