CN110760292B - Heat-resistant friction material and application thereof - Google Patents
Heat-resistant friction material and application thereof Download PDFInfo
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- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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Abstract
The invention discloses a heat-resistant 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, bismaleimide and alumina, and curing to obtain the heat-resistant friction material. The heat-resistant friction material prepared by the invention not only has good wear resistance, heat resistance and mechanical property, but also can realize remolding under the hot-pressing condition, and has wide application prospect.
Description
Technical Field
The invention relates to a heat-resistant friction material and preparation and remodeling methods thereof, belonging to the field of thermosetting shape memory polymers and recyclable polymers.
Background
Thermal performance is an important property for friction materials, and poor heat resistance can lead to reduced service life and limited service conditions of friction materials during friction.
Bismaleimide is a thermosetting resin, has excellent mechanical property 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 main resin) for modifying other substances, and the reasonable process for preparing the bismaleimide resin has good practical significance.
In addition, 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 are caused. Recently, remoldable thermosetting SMPs developed cannot combine high heat resistance, high mechanical properties and good shape memory properties, and cannot be applied as wear-resistant materials.
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 heat-resistant friction material prepared by a method comprising the steps of:
(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 heat-resistant friction material system; the filler system comprises epoxy resin and alumina;
(3) and carrying out hot-pressing curing and post-treatment on the heat-resistant friction material system to obtain the heat-resistant 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 heat-resistant friction material system; the filler system comprises epoxy resin and alumina;
(3) carrying out hot-pressing curing and post-treatment on the heat-resistant friction material system to obtain the heat-resistant friction material;
(4) and carrying out hot pressing treatment on the cracked heat-resistant friction material to obtain a repaired wear-resistant material, thereby realizing self repair of the heat-resistant friction material.
The invention adds epoxy resin into ethanol containing alumina, stirs for 2 hours and then dries to obtain a filler system, which is composed of epoxy resin and alumina; the epoxy resin is bisphenol A epoxy resin; the particle size of the alumina is 0.3-0.4 micron. Preferably, the epoxy resin is 10% by mass of the alumina.
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 a filler system is 50: 75-80: 6-6.5: 3.5, the stirring temperature is 130-135 ℃, and the stirring time is 50-60 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 heat-resistant friction material in preparing wear-resistant objects.
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 heat-resistant 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 remodelable shape memory thermosetting resin reported in the prior literature, the heat-resistant friction material prepared by the invention has outstanding heat resistance and is expressed by the initial thermal decomposition temperature (T)di) Up to 369 deg.C, glass transition temperature (T)g) Up to 191 ℃. The good heat resistance of the heat-resistant friction material benefits from the reasonable formula and preparation process of a resin system and a large number of benzene rings in the resin and six-membered rings formed by curing and other annular structures.
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 heat-resistant 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 heat-resistant friction material system; the filler system comprises epoxy resin and alumina;
(3) and carrying out hot-pressing curing and post-treatment on the heat-resistant friction material system to obtain the heat-resistant friction material.
Synthesis example
120g of 2-allylphenol, 140g of sodium hydroxide, and,Mixing 10g of tetrabutylammonium bromide and 230g of tetrahydrofuran, and reacting for 1.5 hours 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.
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 for use in the following examples and comparative example one.
EXAMPLE preparation of Heat-resistant 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 3.5g of a filler system, stirring at 130 ℃, and carrying out 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 demoulding to obtain the heat-resistant friction material, and testing TG, DMA, bending strength and wear resistance.
EXAMPLE two self-repairing method of Heat-resistant Friction Material and self-repaired wear-resistant Material
The heat-resistant friction material of the first embodiment is placed into a preheated die at 200 ℃ after cracking (stainless steel hammer striking and irregular cracking into three pieces) (crack contact), and then 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 bending strength 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.
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 heat-resistant friction material of the example of the present invention and the prepolymer of the diallyl bisphenol a modified bismaleimide resin of the comparative example one under a nitrogen atmosphere, it can be seen that the maximum exothermic reaction peak of the prepolymer of the heat-resistant friction material of the example is 239.8 ℃ which is lower than 250.3 ℃ of the diallyl bisphenol a modified bismaleimide resin, indicating that the reactivity of the prepolymer of the heat-resistant 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 flexural strength was tested in a universal tester (80 mm 15mm 4 mm).
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 heat-resistant friction material, and testing TG 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 3.5g of a filler system, 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 heat-resistant friction material, and testing TG and wear resistance. In the comparative example, 0.75gKH-550 (1.5 wt%) was added to 200g of ethanol containing 50g 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.
Table 1 shows the above examples and the comparative example, and it can be seen that the alumina compounded with epoxy resin together with bismaleimide exhibits excellent wear resistance while ensuring heat resistance.
Claims (4)
1. A heat-resistant friction material is characterized in that the preparation method of the heat-resistant 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 heat-resistant friction material system; the filler system comprises epoxy resin and alumina;
(3) carrying out hot-pressing curing and post-treatment on the heat-resistant friction material system to obtain the heat-resistant friction material;
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 a filler system is 50: 75-80: 6-6.5: 3.5, the stirring temperature is 130-135 ℃, and the stirring time is 50-60 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;
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 epoxy resin is bisphenol A epoxy resin; the particle size of the alumina is 0.3-0.4 micron.
2. The heat-resistant friction material according to claim 1, wherein 2-allylphenyl glycidyl ether is prepared by adding epichlorohydrin to a mixed solution of 2-allylphenol, sodium hydroxide, a quaternary ammonium salt and tetrahydrofuran, and reacting the mixture.
3. The heat-resistant friction material according to claim 1, wherein the filler system is obtained by adding an epoxy resin to ethanol containing alumina, stirring for 2 hours, and then drying.
4. Use of the heat-resistant friction material according to claim 1 for the production of an abrasion resistant article.
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