CN108641337B - Polyphenyl ether-polysiloxane photo-crosslinking damping material and preparation method thereof - Google Patents

Polyphenyl ether-polysiloxane photo-crosslinking damping material and preparation method thereof Download PDF

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CN108641337B
CN108641337B CN201810476010.0A CN201810476010A CN108641337B CN 108641337 B CN108641337 B CN 108641337B CN 201810476010 A CN201810476010 A CN 201810476010A CN 108641337 B CN108641337 B CN 108641337B
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polysiloxane
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polyphenyl ether
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CN108641337A (en
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梁国正
申达
顾嫒娟
袁莉
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Suzhou University
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Abstract

The invention relates to a polyphenyl ether-polysiloxane photo-crosslinking damping material and a preparation method thereof. The method comprises the following steps that under the action of a free radical initiator and N-bromosuccinimide, methyl on a benzene ring of the polyphenylene oxide is subjected to bromination reaction to obtain brominated polyphenylene oxide. The brominated polyphenylene ether is reacted with allylmagnesium bromide to give an allylated polyphenylene ether. Adding a proper amount of photoinitiator and polythiol into an allyl polyphenyl ether-vinyl polysiloxane solution prepared according to a certain proportion, crosslinking and curing under the irradiation of an ultraviolet lamp, and drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking damping material. Compared with the prior art, the polyphenyl ether-polysiloxane damping material disclosed by the invention has the characteristics of high temperature resistance and wide temperature range, the temperature range for displaying the damping performance is 143-223 ℃, and the maximum effective damping temperature range reaches 75 ℃. In addition, the preparation method of photo-crosslinking meets the basic requirements of rapid industrial production and energy conservation.

Description

Polyphenyl ether-polysiloxane photo-crosslinking damping material and preparation method thereof
Technical Field
The invention relates to a polyphenyl ether-polysiloxane photo-crosslinking damping film and a preparation method thereof, belonging to the field of high polymer materials.
Technical Field
With the increasing problem of noise pollution and poor vibration, the loss factor (tan) is higher) The polymer damping material is widely applied to the industries of aerospace, automobiles, buildings and the like, and becomes a key material which is urgently needed in the advanced industrial fields of high-speed trains, aircrafts and the like. However, the polymer damper material has a problem of poor heat resistance. In particular, when high speed trains and aircraft are operating at high speeds,severe vibration is generated and the temperature of the fuselage is in a higher temperature range, so that a higher temperature condition (>140 ℃ C.) shows damping performance and effectively damps temperature range (tan)Temperature range not less than 0.3) wide (not less than 60 ℃).
At present, the polymer damping materials are mainly classified into three categories, namely rubber, polyurethane and epoxy resin. The ENREF9 rubber and the polyurethane damping material respectively show high damping performance at 0 ℃ or below and 0-90 ℃, and do not meet the requirement of showing the damping performance at higher temperature (140 ℃). Most epoxy resins also show a damping performance at a temperature lower than 140 c, and the prior art has been expected to show a damping performance in a higher temperature range by filling ceramics into the epoxy resin, but the content of piezoelectric ceramics is as high as 38wt% and 44wt%, respectively, deteriorating the manufacturability of the resin, and in addition, the curing temperature of such epoxy resins is high (150 c), the time is long (7 h), and it is not industrially feasible. Therefore, the existing polymer damping material cannot have good manufacturability, high temperature resistance and wide temperature range performance.
The photo-crosslinking has the advantages of high efficiency and energy saving, and is primarily applied to damping materials. At present, the photo-crosslinking damping materials are mainly classified into polyurethanes, acrylates, thiol-olefin systems and the like, but the photo-crosslinking damping materials cannot have both high heat resistance and wide temperature range characteristics.
In conclusion, the development of high temperature resistant and wide temperature range damping materials by adopting a rapid energy-saving method is still a huge challenge with practical value.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a polyphenyl ether-polysiloxane cross-linked damping material and a preparation method thereof.
The invention adopts the following technical scheme:
a preparation method of a polyphenylene oxide-polysiloxane photo-crosslinking material comprises the following steps:
(1) adding benzoyl peroxide and N-bromosuccinimide into an aromatic hydrocarbon solvent containing polyphenyl ether under nitrogen, and carrying out reflux reaction to obtain brominated polyphenyl ether;
(2) under nitrogen, dropwise adding allyl magnesium bromide into tetrahydrofuran containing brominated polyphenylene oxide at 0-60 ℃, and reacting to obtain allylated polyphenylene oxide;
(3) adding allylated polyphenyl ether, polysiloxane, polythiol and a photoinitiator into tetrahydrofuran to obtain a polyphenyl ether-polysiloxane photo-crosslinked system; and carrying out ultraviolet irradiation reaction on the polyphenylene oxide-polysiloxane photo-crosslinked system to obtain the polyphenylene oxide-polysiloxane photo-crosslinked material.
A method for preparing a polyphenylene oxide-polysiloxane photo-crosslinked system comprises the following steps:
(1) adding benzoyl peroxide and N-bromosuccinimide into an aromatic hydrocarbon solvent containing polyphenyl ether under nitrogen, and carrying out reflux reaction to obtain brominated polyphenyl ether;
(2) under nitrogen, dropwise adding allyl magnesium bromide into tetrahydrofuran containing brominated polyphenylene oxide at 0-60 ℃, and reacting to obtain allylated polyphenylene oxide;
(3) adding allylated polyphenyl ether, polysiloxane, polythiol and a photoinitiator into tetrahydrofuran to obtain the polyphenyl ether-polysiloxane photo-crosslinked system.
A preparation method of allylated polyphenylene ether comprises the following steps:
(1) adding benzoyl peroxide and N-bromosuccinimide into an aromatic hydrocarbon solvent containing polyphenyl ether under nitrogen, and carrying out reflux reaction to obtain brominated polyphenyl ether;
(2) and dropwise adding allyl magnesium bromide into tetrahydrofuran containing brominated polyphenylene oxide at 0-60 ℃ under nitrogen, and reacting to obtain the allylated polyphenylene oxide.
In the above technical scheme, the aromatic hydrocarbon solvent is one of toluene and chlorobenzene, or any combination thereof; the polythiol is one of trimethylolpropane tri (3-mercaptopropionate), pentaerythritol tetra (3-mercaptopropionate) and a polymer containing a plurality of thiol groups, or any combination thereof; the photoinitiator is one of (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, N-dimethyl-4-pyridylamine and benzoin dimethyl ether, or any combination thereof; the polysiloxane has the following structural formula:
Figure 578625DEST_PATH_IMAGE001
wherein R is1Is one of vinyl, methyl and hydroxyl, R2Is one of methyl, vinyl and trifluoropropylmethyl.
Preferably, the polysiloxane has the number average molecular weight of 5000-50000 and contains two or more carbon-carbon unsaturated bonds, wherein m + n is more than 65 and less than or equal to 650; the plurality is 3 and more than 3.
In the technical scheme, in the step (1), the mass ratio of the benzoyl peroxide to the N-bromosuccinimide to the polyphenyl ether is (5-15) to (25-80) to 100, and the reflux reaction time is 1-6 hours;
in the step (2), the mass ratio of the allyl magnesium bromide to the brominated polyphenylene oxide is (5-40) to 100, and the reaction time is 1-6 h;
in the step (3), the mass ratio of the allylated polyphenylene ether to the polysiloxane to the polythiol to the photoinitiator is 100: 5-70: 10-20: 2-5, the wavelength of the ultraviolet irradiation reaction is 365nm, and the time is 2-8 minutes.
The invention also discloses the polyphenylene oxide-polysiloxane photo-crosslinking material prepared by the preparation method of the polyphenylene oxide-polysiloxane photo-crosslinking material; and a polyphenylene ether-polysiloxane photocrosslinked system prepared by the above method for preparing a polyphenylene ether-polysiloxane photocrosslinked system; or an allylated polyphenylene ether prepared by the above method for preparing an allylated polyphenylene ether. Also discloses the application of the allylated polyphenyl ether or polyphenyl ether-polysiloxane photo-crosslinking system in the preparation of the polyphenyl ether-polysiloxane photo-crosslinking material.
The preparation method of the polyphenylene oxide-polysiloxane photo-crosslinking material disclosed by the invention can be carried out according to the following steps:
by mass, the amount of the solvent to be added,
(1) under the protection of nitrogen, 100 parts of polyphenyl ether is dissolved in 1000-2000 parts of aromatic hydrocarbon solvent, and then 5-15 parts of benzoyl peroxide and 25-80 parts of N-bromosuccinimide are sequentially added; heating and refluxing for 1-6 h; and (3) precipitating a product by using an alcohol solvent, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Dissolving 100 parts of brominated polyphenylene oxide obtained in the step (1) in 5000 parts of tetrahydrofuran at the temperature of 0-60 ℃ under the protection of nitrogen; then, dropwise adding 5-40 parts of allyl magnesium bromide; after the dropwise addition is finished, reacting for 1-6 h at 0-60 ℃; and (3) precipitating a product by using an alcohol solvent, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) And (3) dissolving 100 parts of allyl polyphenyl ether prepared in the step (3), 5-70 parts of polysiloxane, 10-20 parts of polyhydric thiol and 2-5 parts of photoinitiator in 5000 parts of tetrahydrofuran to obtain a solution A.
(4) And leveling the solution A on a carrier, irradiating for 2-8 min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking material which is a film.
The alcohol solvent is one of methanol, ethanol, n-propanol, isopropanol and n-butanol, or any combination thereof; the support should not adhere to the polyphenylene ether-polysiloxane photocrosslinked film, such as a polytetrafluoroethylene support, a glass support, or an aluminum alloy support.
The effective damping temperature of the polyphenyl ether-polysiloxane photo-crosslinking damping material prepared by the invention is concentrated at 143-223 ℃, and the effective damping temperature ranges are all more than 60 ℃, so that the polyphenyl ether-polysiloxane photo-crosslinking damping material is a damping material capable of showing wide temperature range characteristics at high temperature; meanwhile, the polyphenyl ether-polysiloxane photo-crosslinking damping film disclosed by the invention adopts a photo-crosslinking preparation process, has the characteristics of high efficiency and energy saving, and solves the process problems of energy consumption and time consumption of common high-temperature-resistant damping materials. The photo-crosslinking damping material prepared by the invention has the advantages of high-efficiency and energy-saving process, wide temperature range damping performance and excellent high-temperature resistance.
Compared with the prior art, the invention has the beneficial effects that:
1. the polyphenyl ether-polysiloxane photo-crosslinking damping material prepared by the invention has excellent damping performance under a high temperature condition (143-223 ℃), the effective damping temperature range is higher than 60 ℃ and can reach 75 ℃ at most, and thus a reliable foundation is provided for the application of the polyphenyl ether-polysiloxane photo-crosslinking damping material in the fields of aerospace, military, high-speed trains and the like. The excellent performances are mainly benefited by the fact that the polyphenylene oxide-polysiloxane photo-crosslinking material has a proper phase dispersion degree, a unique photo-crosslinking network structure and a high glass transition temperature of the polyphenylene oxide.
2. The polyphenyl ether-polysiloxane photo-crosslinking damping material prepared by the invention has high damping efficiency, and the loss factor is about 0.8. This is mainly because polyfluorosiloxane has a large polar side group, which can increase the internal consumption of the material; in addition, the molecular chain movement capacity of the photo-crosslinking film can be improved by adding the high-flexibility polyfluorosiloxane molecular chain, so that more mechanical energy can be converted into internal energy to be consumed when the material is subjected to external force.
3. The polyphenyl ether-polysiloxane photo-crosslinking damping material prepared by the invention has good heat resistance, the glass transition temperature of the material is concentrated at 190-200 ℃, the initial thermal decomposition temperature (the temperature with 5wt% mass loss) can reach 250 ℃ (nitrogen atmosphere, and the heating rate is 10 ℃/min). This is mainly attributed to the crosslinked network structure of the photo-crosslinking material, and the excellent heat resistance of polyphenylene ether and polysiloxane themselves.
4. The polyphenyl ether-polysiloxane photo-crosslinking damping material prepared by the invention adopts a photo-crosslinking preparation process, has the characteristics of high efficiency and energy conservation, is mild in reaction condition, easy to control and realize, and convenient for industrial production.
Drawings
FIG. 1 is a synthesis scheme of an allyl polyphenylene ether prepared in example 1 of the present invention;
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of allyl polyphenylene ether prepared in example 1 of the present invention (1H-NMR）；
FIG. 3 is a Fourier Infrared (FTIR) spectrum of an allyl polyphenylene ether prepared in example 1 of the present invention;
FIG. 4 is a graph showing a loss factor vs. temperature curve (obtained by dynamic mechanical analysis DMA test) of the polyphenylene ether-polysiloxane photo-crosslinked films prepared in examples 1, 2 and 3 of the present invention, the polyphenylene ether photo-crosslinked film prepared in comparative example 1 and the polyphenylene ether-polysiloxane photo-crosslinked film prepared in comparative example 2;
FIG. 5 is a thermogravimetric analysis (TGA) curve (nitrogen atmosphere, temperature rise rate of 10 ℃/min) of the polyphenylene ether-polysiloxane photo-crosslinked films prepared in examples 1, 2 and 3 of the present invention, the polyphenylene ether photo-crosslinked film prepared in comparative example 1 and the polyphenylene ether-polysiloxane photo-crosslinked film prepared in comparative example 2.
Detailed Description
The technical solution of the present invention will be further described with reference to the accompanying drawings, examples and comparative examples.
Example 1
(1) Preparation of brominated polyphenylene ethers
Referring to FIG. 1, there is shown a reaction scheme for the synthesis of allyl polyphenylene ether according to the invention. In this embodiment, the specific method is as follows: under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 100mL of chlorobenzene, then 1g of benzoyl peroxide and 4g of N-bromosuccinimide are sequentially added, and heating reflux reaction is carried out for 1.5 h; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 40 ℃ under the protection of nitrogen, dropwise adding 20mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 3h at the temperature of 40 ℃; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the allylated polyphenyl ether. Its nuclear magnetic resonance hydrogen spectrum (1H-NMR) and Fourier infrared (FTIR) spectra are shown in figures 2 and 3, respectively.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
0.95g of allylated polyphenylene ether, 0.05g of vinyl polytrifluoropropylmethylsiloxane, 0.12g of trimethylolpropane tris (3-mercaptopropionate), and 0.03g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide were dissolved in 50mL of tetrahydrofuran to obtain a solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 5min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film. The loss factor-temperature curve (obtained by dynamic mechanical analysis DMA test) and the thermogravimetric analysis (TGA) curve are respectively shown in figure 4 and figure 5.
Referring to FIG. 2, which is a nuclear magnetic resonance hydrogen spectrum of allyl polyphenylene ether prepared in example 1: (1H-NMR). As can be seen from the figure, the peaks at c (= 4.9 ppm) and d (= 5.7 ppm) are-CH2-CH=CH2The formant of the hydrogen atom of the middle double bond indicates that the allyl polyphenyl ether is successfully synthesized. Further, according to1The grafting ratio of the allyl polyphenylene ether can be obtained by the ratio of the proton peak integral area of the double bond and the methyl group on the benzene ring in H-NMR. The allyl graft ratio of the polyphenylene ether was calculated to be 10.6%, i.e., y: z = 197: 58.
Referring to FIG. 3, a Fourier Infrared (FTIR) spectrum of the allyl polyphenylene ether prepared in example 1 is shown. As can be seen, at 913cm-1An out-of-plane flexural vibration peak of the allyl group appears at the wavelength, also indicating successful allylation of the polyphenylene ether.
Example 2
0.9g of the allylated polyphenylene ether prepared in example 1, 0.1g of vinyl polytrifluoropropylmethylsiloxane, 0.12g of trimethylolpropane tris (3-mercaptopropionate), and 0.03g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide were dissolved in 50mL of tetrahydrofuran to obtain solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 5min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film. The loss factor-temperature curve (obtained by dynamic mechanical analysis DMA test) and the thermogravimetric analysis (TGA) curve are respectively shown in figure 4 and figure 5.
Example 3
0.85g of the allylated polyphenylene ether prepared in example 1, 0.15g of vinyl polytrifluoropropylmethylsiloxane, 0.11g of trimethylolpropane tris (3-mercaptopropionate), and 0.03g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide were dissolved in 50mL of tetrahydrofuran to obtain solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 5min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film. The loss factor-temperature curve (obtained by dynamic mechanical analysis DMA test) and the thermogravimetric analysis (TGA) curve are respectively shown in figure 4 and figure 5.
Comparative example 1 preparation of polyphenylene ether photo-crosslinked film
1g of allyl polyphenylene ether prepared in example 1, 0.13g of trimethylolpropane tris (3-mercaptopropionate), and 0.03g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide were dissolved in 45mL of tetrahydrofuran to obtain a solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 5min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenylene oxide photo-crosslinking film. The loss factor-temperature curve (obtained by dynamic mechanical analysis DMA test) and the thermogravimetric analysis (TGA) curve are respectively shown in figure 4 and figure 5.
Comparative example 2 polyphenylene ether-polysiloxane photo-crosslinked film
0.5g of the allylated polyphenylene ether prepared in example 1, 0.5g of vinyl polytrifluoropropylmethylsiloxane, 0.08g of trimethylolpropane tris (3-mercaptopropionate), and 0.03g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide were dissolved in 50mL of tetrahydrofuran to obtain solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 5min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film. The loss factor-temperature curve (obtained by dynamic mechanical analysis DMA test) and the thermogravimetric analysis (TGA) curve are respectively shown in figure 4 and figure 5.
Referring to FIG. 4, there are shown graphs of dissipation factor vs. temperature (obtained by dynamic mechanical analysis DMA test) of the polyphenylene ether-polysiloxane photo-crosslinked films prepared in examples 1, 2 and 3 of the present invention, the polyphenylene ether photo-crosslinked film prepared in comparative example 1 and the polyphenylene ether-polysiloxane photo-crosslinked film prepared in comparative example 2. As can be seen from the figure, the effective damping temperature ranges of the polyphenylene ether photo-crosslinked film prepared in comparative example 1 and the polyphenylene ether-polysiloxane photo-crosslinked film prepared in comparative example 2 were 51 ℃ (166 to 218 ℃) and 49 ℃ (156 to 205 ℃), respectively, and both of them did not meet the requirement of wide temperature range (> 60 ℃). In contrast, the polyphenylene ether-polysiloxane photo-crosslinked films prepared in examples 1, 2 and 3 had effective damping temperature ranges of 62 deg.C (153-213 deg.C), 75 deg.C (142-217 deg.C) and 65 deg.C (158-223 deg.C), respectively, all of which met the requirement of wide temperature range. On the other hand, the loss factors of the polyphenylene ether photo-crosslinked film prepared in comparative example 1 and the polyphenylene ether-polysiloxane photo-crosslinked film prepared in comparative example 2 were 0.60 and 0.54, respectively, while the loss factors of the polyphenylene ether-polysiloxane photo-crosslinked films prepared in examples 1, 2 and 3 were 0.80, 0.78 and 0.77, respectively, indicating that the presence of a limited amount of polyfluorosiloxane can significantly improve the damping performance of the polyphenylene ether photo-crosslinked film. In addition, the effective damping temperature of the polyphenylene ether-polysiloxane photo-crosslinked films prepared in examples 1, 2 and 3 was concentrated in the high temperature range of 143 to 223 ℃. In conclusion, the polyphenylene ether-polysiloxane photo-crosslinked films prepared in examples 1, 2 and 3 satisfy both high temperature resistance and wide temperature range.
Referring to FIG. 5, there are shown thermal weight loss (TGA) curves of the polyphenylene ether-polysiloxane photo-crosslinked films prepared in examples 1, 2 and 3, the polyphenylene ether photo-crosslinked film prepared in comparative example 1 and the polyphenylene ether-polysiloxane photo-crosslinked film prepared in comparative example 2. As can be seen, the initial thermal decomposition temperature (temperature at which 5wt% of mass is lost) of comparative example 1 was 213 ℃; the initial thermal decomposition temperatures of the polyphenylene ether-polysiloxane photo-crosslinked films prepared in examples 1, 2 and 3 and the polyphenylene ether-polysiloxane photo-crosslinked film prepared in comparative example 2 were 232 ℃, 236 ℃, 249 ℃ and 253 ℃, respectively, indicating that the addition of the polyfluorosiloxane can significantly improve the thermal stability of the polyphenylene ether photo-cured film.
Example 4
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenylene oxide is dissolved in a mixed solvent of 50mL of chlorobenzene and 50mL of toluene, then 1g of benzoyl peroxide and 4g N-bromosuccinimide are sequentially added, and heating reflux reaction is carried out for 1.5 h; and (3) precipitating a product by using ethanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 40 ℃ under the protection of nitrogen, dropwise adding 3.4mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 3h at the temperature of 40 ℃ after dropwise adding; and (3) precipitating a product by using ethanol, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
0.95g of allylated polyphenylene ether, 0.05g of vinyl polytrifluoropropylmethylsiloxane, 0.12g of trimethylolpropane tris (3-mercaptopropionate), and 0.03g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide were dissolved in 50mL of tetrahydrofuran to obtain a solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 5min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film, wherein the effective damping temperature range is 63 ℃, and the polyphenyl ether-polysiloxane photo-crosslinking film is a damping material capable of showing wide temperature range characteristics at high temperature.
Example 5
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 125mL of chlorobenzene, then 1g of benzoyl peroxide and 4g N-bromosuccinimide are sequentially added, and heating reflux reaction is carried out for 1.5 h; and (3) precipitating a product by using an ethanol solution containing 50% of methanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 40 ℃ under the protection of nitrogen, dropwise adding 27.6mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 3h at the temperature of 40 ℃ after dropwise adding; precipitating the product by using an ethanol solution containing 50% of methanol, washing, filtering and drying to obtain the allylated polyphenylene ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
0.95g of allylated polyphenylene ether, 0.05g of vinyl polytrifluoropropylmethylsiloxane, 0.12g of trimethylolpropane tris (3-mercaptopropionate), and 0.04g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide were dissolved in 50mL of tetrahydrofuran to obtain a solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 2min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film, wherein the effective damping temperature range is 62 ℃, and the polyphenyl ether-polysiloxane photo-crosslinking film is a damping material capable of showing wide temperature range characteristics at high temperature.
Example 6
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 200mL of chlorobenzene, then 1.5g of benzoyl peroxide and 2.5g N-bromosuccinimide are sequentially added, and heating reflux reaction is carried out for 6 hours; and (3) precipitating a product by using isopropanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 40 ℃ under the protection of nitrogen, dropwise adding 20mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 3h at the temperature of 40 ℃; and (3) precipitating a product by using isopropanol, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
0.95g of allylated polyphenylene ether, 0.05g of vinyl polytrifluoropropylmethylsiloxane, 0.06g of trimethylolpropane tris (3-mercaptopropionate), 0.06g of pentaerythritol tetrakis (3-mercaptopropionate), and 0.02g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide were dissolved in 50mL of tetrahydrofuran to obtain a solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 5min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film with the effective damping temperature range of 68 ℃, wherein the polyphenyl ether-polysiloxane photo-crosslinking film is a damping material capable of showing wide temperature range characteristics at high temperature.
Example 7
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 100mL of toluene, then 1g of benzoyl peroxide and 4g N-bromosuccinimide are sequentially added, and the heating reflux reaction is carried out for 1.5 h; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 60 ℃ under the protection of nitrogen, dropwise adding 20mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 1h at 60 ℃; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
0.95g of allylated polyphenylene ether, 0.05g of vinyl polytrifluoropropylmethylsiloxane, 0.19g of pentaerythritol tetrakis (3-mercaptopropionate), and 0.03g N, N-dimethyl-4-pyridylamine were dissolved in 50mL of tetrahydrofuran to obtain a solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 5min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film, wherein the effective damping temperature range is 65 ℃, and the polyphenyl ether-polysiloxane photo-crosslinking film is a damping material capable of showing wide temperature range characteristics at high temperature.
Example 8
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 100mL of chlorobenzene, then 0.5g of benzoyl peroxide and 8g N-bromosuccinimide are sequentially added, and heating reflux reaction is carried out for 1 h; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 40 ℃ under the protection of nitrogen, dropwise adding 20mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 3h at the temperature of 40 ℃; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
0.95g of allylated polyphenylene ether, 0.05g of vinyl polydimethysiloxane, 0.05g of pentaerythritol tetrakis (3-mercaptopropionate), and 0.03g of benzoin bis-methyl ether were dissolved in 50mL of tetrahydrofuran to obtain solution A.
And leveling the solution A on an aluminum alloy carrier, irradiating for 8min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film, wherein the effective damping temperature range is 64 ℃, and the polyphenyl ether-polysiloxane photo-crosslinking film is a damping material capable of showing wide temperature range characteristics at high temperature.
Example 9
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 125mL of chlorobenzene, then 1g of benzoyl peroxide and 4g N-bromosuccinimide are sequentially added, and heating reflux reaction is carried out for 1.5 h; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 0 ℃ under the protection of nitrogen, dropwise adding 20mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 6h at the temperature of 0 ℃ after dropwise adding; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
0.95g of allylated polyphenylene ether, 0.05g of vinyl polydimethylsiloxane, 0.13g of pentaerythritol tetrakis (3-mercaptopropionate), 0.02g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide and 0.01g of benzoin bis-methyl ether were dissolved in 50mL of tetrahydrofuran to obtain a solution A.
Leveling the solution A on a glass carrier, irradiating for 2min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film.
Example 10
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 100mL of chlorobenzene, then 0.5g of benzoyl peroxide and 2.5g N-bromosuccinimide are sequentially added, and heating reflux reaction is carried out for 6 hours; and (3) precipitating a product by using ethanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 60 ℃ under the protection of nitrogen, dropwise adding 3.4mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 1h at 60 ℃ after dropwise adding; and (3) precipitating a product by using ethanol, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) Preparation of polyphenylene oxide-polysiloxane photo-crosslinked damping film (thiol)
0.9g of allylated polyphenylene ether, 0.1g of vinyl polytrifluoropropylmethylsiloxane, 0.09g of trimethylolpropane tris (3-mercaptopropionate), and 0.03g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide were dissolved in 50mL of tetrahydrofuran to obtain a solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 5min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film.
Example 11
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 200mL of chlorobenzene, then 1.5g of benzoyl peroxide and 8g N-bromosuccinimide are sequentially added, and heating reflux reaction is carried out for 1 h; and (3) precipitating a product by using isopropanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 60 ℃ under the protection of nitrogen, dropwise adding 27.6mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 1h at 60 ℃ after dropwise adding; and (3) precipitating a product by using isopropanol, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
0.9g of allylated polyphenylene ether, 0.1g of vinyl polytrifluoropropylmethylsiloxane, 0.18g of trimethylolpropane tris (3-mercaptopropionate), and 0.03g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide were dissolved in 50mL of tetrahydrofuran to obtain a solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 5min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film.
Example 12
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 125mL of toluene, then 1g of benzoyl peroxide and 4g N-bromosuccinimide are sequentially added, and the heating reflux reaction is carried out for 1.5 h; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 40 ℃ under the protection of nitrogen, dropwise adding 20mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 3h at the temperature of 40 ℃; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
0.9g of allylated polyphenylene ether, 0.1g of vinyl polytrifluoropropylmethylsiloxane, 0.13g of pentaerythritol tetrakis (3-mercaptopropionate), and 0.04g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide were dissolved in 50mL of tetrahydrofuran to obtain a solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 5min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film.
Example 13
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 125mL of chlorobenzene, then 0.5g of benzoyl peroxide and 2.5g N-bromosuccinimide are sequentially added, and heating reflux reaction is carried out for 1.5 h; and (3) precipitating a product by using ethanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 60 ℃ under the protection of nitrogen, dropwise adding 3.4mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 1h at 60 ℃ after dropwise adding; and (3) precipitating a product by using ethanol, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
0.90g of allylated polyphenylene ether, 0.1g of vinyl polytrifluoropropylmethylsiloxane, 0.09g of pentaerythritol tetrakis (3-mercaptopropionate), and 0.02g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide were dissolved in 50mL of tetrahydrofuran to obtain a solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 5min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film.
Example 14
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 125mL of chlorobenzene, then 1.5g of benzoyl peroxide and 8g N-bromosuccinimide are sequentially added, and the heating reflux reaction is carried out for 1.5 h; and (3) precipitating a product by using isopropanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 60 ℃ under the protection of nitrogen, dropwise adding 27.6mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 1h at 60 ℃ after dropwise adding; and (3) precipitating a product by using isopropanol, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
0.9g of allylated polyphenylene ether, 0.1g of vinyl polytrifluoropropylmethylsiloxane, 0.18g of pentaerythritol tetrakis (3-mercaptopropionate), and 0.03g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide were dissolved in 50mL of tetrahydrofuran to obtain a solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 5min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film.
Example 15
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 125mL of chlorobenzene, then 1g of benzoyl peroxide and 4g N-bromosuccinimide are sequentially added, and heating reflux reaction is carried out for 1.5 h; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 0 ℃ under the protection of nitrogen, dropwise adding 20mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 6h at the temperature of 0 ℃ after dropwise adding; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
0.9g of allylated polyphenylene ether, 0.1g of vinyl polytrifluoropropylmethylsiloxane, 0.13g of pentaerythritol tetrakis (3-mercaptopropionate), and 0.03g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide were dissolved in 50mL of tetrahydrofuran to obtain a solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 8min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film.
Example 16
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 125mL of chlorobenzene, then 1g of benzoyl peroxide and 4g N-bromosuccinimide are sequentially added, and heating reflux reaction is carried out for 1.5 h; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 40 ℃ under the protection of nitrogen, dropwise adding 20mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 6h at the temperature of 40 ℃; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
0.9g of allylated polyphenylene ether, 0.1g of vinyl polydimethylsiloxane, 0.13g of pentaerythritol tetrakis (3-mercaptopropionate) and 0.03g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide were dissolved in 50mL of tetrahydrofuran to obtain a solution A.
Leveling the solution A on a glass carrier, irradiating for 8min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film.
Example 17
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 125mL of chlorobenzene, then 1g of benzoyl peroxide and 4g N-bromosuccinimide are sequentially added, and heating reflux reaction is carried out for 1.5 h; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 40 ℃ under the protection of nitrogen, dropwise adding 20mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 6h at the temperature of 40 ℃; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
0.9g of allylated polyphenylene ether, 0.1g of vinyl polydimethylsiloxane, 0.13g of pentaerythritol tetrakis (3-mercaptopropionate) and 0.03g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide were dissolved in 50mL of tetrahydrofuran to obtain a solution A.
Leveling the solution A on an aluminum alloy carrier, irradiating for 8min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film.
Example 18
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 125mL of toluene, then 1g of benzoyl peroxide and 4g N-bromosuccinimide are sequentially added, and the heating reflux reaction is carried out for 1.5 h; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 40 ℃ under the protection of nitrogen, dropwise adding 20mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 3h at the temperature of 40 ℃; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
0.9g of allylated polyphenylene ether, 0.1g of vinyl polytrifluoropropylmethylsiloxane, 0.13g of pentaerythritol tetrakis (3-mercaptopropionate), and 0.03g N, N-dimethyl-4-pyridylamine were dissolved in 50mL of tetrahydrofuran to obtain a solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 5min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film.
Example 19
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 125mL of toluene, then 1g of benzoyl peroxide and 4g N-bromosuccinimide are sequentially added, and the heating reflux reaction is carried out for 1.5 h; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 40 ℃ under the protection of nitrogen, dropwise adding 20mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 3h at the temperature of 40 ℃; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
0.9g of allylated polyphenylene ether, 0.1g of vinyl polytrifluoropropylmethylsiloxane, 0.13g of pentaerythritol tetrakis (3-mercaptopropionate), and 0.03g of benzoin bis-methyl ether were dissolved in 50mL of tetrahydrofuran to obtain a solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 5min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film.
Example 20
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 125mL of toluene, then 1g of benzoyl peroxide and 4g N-bromosuccinimide are sequentially added, and the heating reflux reaction is carried out for 1.5 h; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 40 ℃ under the protection of nitrogen, dropwise adding 20mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 3h at the temperature of 40 ℃; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
0.9g of allylated polyphenylene ether, 0.1g of vinyl polytrifluoropropylmethylsiloxane, 0.13g of pentaerythritol tetrakis (3-mercaptopropionate), 0.02g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide and 0.01g of benzoin bis-methyl ether were dissolved in 50mL of tetrahydrofuran to obtain a solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 5min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film.
Example 21
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenylene oxide is dissolved in a mixed solvent of 50mL of chlorobenzene and 50mL of toluene, then 1g of benzoyl peroxide and 4g N-bromosuccinimide are sequentially added, and heating reflux reaction is carried out for 1.5 h; and (3) precipitating a product by using ethanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 40 ℃ under the protection of nitrogen, dropwise adding 3.4mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 3h at the temperature of 40 ℃ after dropwise adding; and (3) precipitating a product by using ethanol, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
0.85g of allylated polyphenylene ether, 0.15g of vinyl polytrifluoropropylmethylsiloxane, 0.11g of trimethylolpropane tris (3-mercaptopropionate), and 0.03g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide were dissolved in 50mL of tetrahydrofuran to obtain a solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 5min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film, wherein the effective damping temperature range is 69 ℃, and the polyphenyl ether-polysiloxane photo-crosslinking film is a damping material capable of showing wide temperature range characteristics at high temperature.
Example 22
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 125mL of chlorobenzene, then 1g of benzoyl peroxide and 4g N-bromosuccinimide are sequentially added, and heating reflux reaction is carried out for 1.5 h; and (3) precipitating a product by using an ethanol solution containing 50% of methanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 40 ℃ under the protection of nitrogen, dropwise adding 27.6mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 3h at the temperature of 40 ℃ after dropwise adding; precipitating the product by using an ethanol solution containing 50% of methanol, washing, filtering and drying to obtain the allylated polyphenylene ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
0.85g of allylated polyphenylene ether, 0.15g of vinyl polydimethylsiloxane, 0.11g of trimethylolpropane tris (3-mercaptopropionate), and 0.04g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide were dissolved in 50mL of tetrahydrofuran to obtain a solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 2min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film.
Example 23
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 200mL of chlorobenzene, then 1.5g of benzoyl peroxide and 2.5g N-bromosuccinimide are sequentially added, and heating reflux reaction is carried out for 6 hours; and (3) precipitating a product by using isopropanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 40 ℃ under the protection of nitrogen, dropwise adding 20mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 3h at the temperature of 40 ℃; and (3) precipitating a product by using isopropanol, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
0.85g of allylated polyphenylene ether, 0.15g of vinyl polydimethylsiloxane, 0.06g of trimethylolpropane tris (3-mercaptopropionate), 0.06g of pentaerythritol tetrakis (3-mercaptopropionate), and 0.02g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide were dissolved in 50mL of tetrahydrofuran to obtain solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 5min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film.
Example 24
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 100mL of toluene, then 1g of benzoyl peroxide and 4g N-bromosuccinimide are sequentially added, and the heating reflux reaction is carried out for 1.5 h; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 60 ℃ under the protection of nitrogen, dropwise adding 20mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 1h at 60 ℃; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
0.85g of allylated polyphenylene ether, 0.15g of vinyl polytrifluoropropylmethylsiloxane, 0.17g of pentaerythritol tetrakis (3-mercaptopropionate), and 0.03g N, N-dimethyl-4-pyridylamine were dissolved in 50mL of tetrahydrofuran to obtain solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 5min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film.
Example 25
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 100mL of chlorobenzene, then 0.5g of benzoyl peroxide and 8g N-bromosuccinimide are sequentially added, and heating reflux reaction is carried out for 1 h; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 40 ℃ under the protection of nitrogen, dropwise adding 20mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 3h at the temperature of 40 ℃; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
0.85g of allylated polyphenylene ether, 0.15g of vinyl polytrifluoropropylmethylsiloxane, 0.04g of pentaerythritol tetrakis (3-mercaptopropionate), and 0.03g of benzoin bis-methyl ether were dissolved in 50mL of tetrahydrofuran to obtain solution A.
And leveling the solution A on an aluminum alloy carrier, irradiating for 8min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film, wherein the effective damping temperature range is 70 ℃, and the polyphenyl ether-polysiloxane photo-crosslinking film is a damping material capable of showing wide temperature range characteristics at high temperature.
Example 26
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 125mL of chlorobenzene, then 1g of benzoyl peroxide and 4g N-bromosuccinimide are sequentially added, and heating reflux reaction is carried out for 1.5 h; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 0 ℃ under the protection of nitrogen, dropwise adding 20mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 6h at the temperature of 0 ℃ after dropwise adding; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
0.85g of allylated polyphenylene ether, 0.15g of vinyl polytrifluoropropylmethylsiloxane, 0.12g of pentaerythritol tetrakis (3-mercaptopropionate), 0.02g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide and 0.01g of benzoin bis-methyl ether were dissolved in 50mL of tetrahydrofuran to obtain a solution A.
Leveling the solution A on a glass carrier, irradiating for 2min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film.
Example 27
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 125mL of chlorobenzene, then 1g of benzoyl peroxide and 4g N-bromosuccinimide are sequentially added, and heating reflux reaction is carried out for 1.5 h; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 40 ℃ under the protection of nitrogen, dropwise adding 20mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 3h at the temperature of 40 ℃; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
1g of allylated polyphenylene ether, 0.7g of vinyl polytrifluoropropylmethylsiloxane, 0.15g of pentaerythritol tetrakis (3-mercaptopropionate), and 0.02g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide were dissolved in 50mL of tetrahydrofuran to obtain a solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 5min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film.
Example 28
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 100mL of toluene, then 0.5g of benzoyl peroxide and 8g N-bromosuccinimide are sequentially added, and the heating reflux reaction is carried out for 1 h; and (3) precipitating a product by using ethanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 0 ℃ under the protection of nitrogen, dropwise adding 20mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 6h at the temperature of 0 ℃ after dropwise adding; and (3) precipitating a product by using ethanol, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
1g of allylated polyphenylene ether, 0.7g of vinyl polytrifluoropropylmethylsiloxane, 0.15g of trimethylolpropane tris (3-mercaptopropionate), and 0.05g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide were dissolved in 50mL of tetrahydrofuran to obtain a solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 8min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film.
Example 29
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 125mL of chlorobenzene, then 1g of benzoyl peroxide and 4g N-bromosuccinimide are sequentially added, and heating reflux reaction is carried out for 1.5 h; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 40 ℃ under the protection of nitrogen, dropwise adding 20mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 3h at the temperature of 40 ℃; and (3) separating out a product by using methanol, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
1g of allylated polyphenylene ether, 0.05g of vinyl polytrifluoropropylmethylsiloxane, 0.15g of pentaerythritol tetrakis (3-mercaptopropionate), and 0.02g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide were dissolved in 50mL of tetrahydrofuran to obtain a solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 5min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film.
Example 30
(1) Preparation of brominated polyphenylene ethers
Under the protection of nitrogen, 10g of polyphenyl ether is dissolved in 100mL of toluene, then 0.5g of benzoyl peroxide and 8g N-bromosuccinimide are sequentially added, and the heating reflux reaction is carried out for 1 h; and (3) precipitating a product by using ethanol, washing, filtering and drying to obtain the brominated polyphenylene oxide.
(2) Preparation of allyl polyphenylene oxide
Dissolving 10g of brominated polyphenylene ether in 500mL of tetrahydrofuran at the temperature of 0 ℃ under the protection of nitrogen, dropwise adding 20mL of allyl magnesium bromide tetrahydrofuran solution (1 mol/L), and reacting for 6h at the temperature of 0 ℃ after dropwise adding; and (3) precipitating a product by using ethanol, washing, filtering and drying to obtain the allylated polyphenyl ether.
(3) Preparation of polyphenyl ether-polysiloxane photo-crosslinking damping film
1g of allylated polyphenylene ether, 0.05g of vinyl polytrifluoropropylmethylsiloxane, 0.15g of trimethylolpropane tris (3-mercaptopropionate), and 0.05g of (2, 4, 6-trimethylbenzoyl) diphenylphosphine oxide were dissolved in 50mL of tetrahydrofuran to obtain a solution A.
And leveling the solution A on a polytetrafluoroethylene carrier, irradiating for 8min under an ultraviolet lamp with the wavelength of 365nm, taking out a sample, and fully drying to obtain the polyphenyl ether-polysiloxane photo-crosslinking film.

Claims (5)

1. The polyphenylene ether-polysiloxane photo-crosslinking material is characterized in that the preparation method of the polyphenylene ether-polysiloxane photo-crosslinking material comprises the following steps:
(1) adding benzoyl peroxide and N-bromosuccinimide into an aromatic hydrocarbon solvent containing polyphenyl ether under nitrogen, and carrying out reflux reaction to obtain brominated polyphenyl ether;
(2) under nitrogen, dropwise adding allyl magnesium bromide into tetrahydrofuran containing brominated polyphenylene oxide at 0-60 ℃, and reacting to obtain allylated polyphenylene oxide;
(3) adding allylated polyphenyl ether, polysiloxane, polythiol and a photoinitiator into tetrahydrofuran to obtain a polyphenyl ether-polysiloxane photo-crosslinked system; carrying out ultraviolet irradiation reaction on the polyphenyl ether-polysiloxane photo-crosslinking system to obtain a polyphenyl ether-polysiloxane photo-crosslinking material; the mass ratio of the allylated polyphenylene ether to the polysiloxane to the polythiol to the photoinitiator is 100: 5-70: 10-20: 2-5;
the polysiloxane has the following structural formula:
Figure 893758DEST_PATH_IMAGE001
wherein R is1Is a vinyl group, and is a vinyl group,R2is one of methyl, vinyl and trifluoropropylmethyl; the polysiloxane has the number average molecular weight of 5000-50000 and contains two or more carbon-carbon unsaturated bonds, wherein m + n is more than or equal to 65 and less than or equal to 650.
2. The polyphenylene ether-polysiloxane photocrosslinkable material according to claim 1, wherein: the aromatic hydrocarbon solvent is one of toluene and chlorobenzene, or any combination thereof; the polythiol is one of trimethylolpropane tri (3-mercaptopropionate), pentaerythritol tetra (3-mercaptopropionate) and a polymer containing a plurality of thiol groups, or any combination thereof; the photoinitiator is one of (2, 4, 6-trimethylbenzoyl) diphenyl phosphine oxide, N-dimethyl-4-pyridylamine and benzoin dimethyl ether, or any combination thereof; the plurality is 3 and more than 3.
3. The polyphenylene ether-polysiloxane photocrosslinkable material according to claim 1, wherein:
in the step (1), the mass ratio of the benzoyl peroxide to the N-bromosuccinimide to the polyphenyl ether is (5-15) to (25-80) to 100, and the reflux reaction time is 1-6 h;
in the step (2), the mass ratio of the allyl magnesium bromide to the brominated polyphenylene oxide is (5-40) to 100, and the reaction time is 1-6 h;
in the step (3), the wavelength of the ultraviolet light reaction is 365 nanometers, and the time is 2-8 minutes.
4. The preparation method of the polyphenylene ether-polysiloxane photo-crosslinked system is characterized by comprising the following steps:
(1) adding benzoyl peroxide and N-bromosuccinimide into an aromatic hydrocarbon solvent containing polyphenyl ether under nitrogen, and carrying out reflux reaction to obtain brominated polyphenyl ether;
(2) under nitrogen, dropwise adding allyl magnesium bromide into tetrahydrofuran containing brominated polyphenylene oxide at 0-60 ℃, and reacting to obtain allylated polyphenylene oxide;
(3) adding allylated polyphenyl ether, polysiloxane, polythiol and a photoinitiator into tetrahydrofuran to obtain a polyphenyl ether-polysiloxane photo-crosslinked system; the mass ratio of the allylated polyphenylene ether to the polysiloxane to the polythiol to the photoinitiator is 100: 5-70: 10-20: 2-5;
the polysiloxane has the following structural formula:
Figure 461270DEST_PATH_IMAGE001
wherein R is1Is vinyl, R2Is one of methyl, vinyl and trifluoropropylmethyl; the polysiloxane has the number average molecular weight of 5000-50000 and contains two or more carbon-carbon unsaturated bonds, wherein m + n is more than or equal to 65 and less than or equal to 650.
5. The polyphenylene ether-polysiloxane photocrosslinked system according to claim 4, wherein:
in the step (1), the mass ratio of the benzoyl peroxide to the N-bromosuccinimide to the polyphenyl ether is (5-15) to (25-80) to 100, and the reflux reaction time is 1-6 h;
in the step (2), the mass ratio of the allyl magnesium bromide to the brominated polyphenylene oxide is (5-40) to 100, and the reaction time is 1-6 h.
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