CN113698607A - Symmetrical tetraphenyl phenyl vinyl silicone oil and preparation method thereof - Google Patents
Symmetrical tetraphenyl phenyl vinyl silicone oil and preparation method thereof Download PDFInfo
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- 229920002545 silicone oil Polymers 0.000 title claims abstract description 75
- -1 tetraphenyl phenyl vinyl Chemical group 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- PLGPSDNOLCVGSS-UHFFFAOYSA-N Tetraphenylcyclopentadienone Chemical compound O=C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PLGPSDNOLCVGSS-UHFFFAOYSA-N 0.000 claims description 21
- 238000010438 heat treatment Methods 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 15
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 10
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- YFKBXYGUSOXJGS-UHFFFAOYSA-N 1,3-Diphenyl-2-propanone Chemical compound C=1C=CC=CC=1CC(=O)CC1=CC=CC=C1 YFKBXYGUSOXJGS-UHFFFAOYSA-N 0.000 claims description 2
- CGYGETOMCSJHJU-UHFFFAOYSA-N 2-chloronaphthalene Chemical compound C1=CC=CC2=CC(Cl)=CC=C21 CGYGETOMCSJHJU-UHFFFAOYSA-N 0.000 claims description 2
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 claims description 2
- AFPRJLBZLPBTPZ-UHFFFAOYSA-N acenaphthoquinone Chemical compound C1=CC(C(C2=O)=O)=C3C2=CC=CC3=C1 AFPRJLBZLPBTPZ-UHFFFAOYSA-N 0.000 claims description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims 1
- 229920002379 silicone rubber Polymers 0.000 abstract description 9
- 239000000853 adhesive Substances 0.000 abstract description 7
- 230000001070 adhesive effect Effects 0.000 abstract description 7
- 239000012752 auxiliary agent Substances 0.000 abstract description 5
- 229920002050 silicone resin Polymers 0.000 abstract description 4
- 239000004945 silicone rubber Substances 0.000 abstract description 3
- 238000004132 cross linking Methods 0.000 abstract description 2
- 239000002861 polymer material Substances 0.000 abstract description 2
- 230000003014 reinforcing effect Effects 0.000 abstract description 2
- 238000003878 thermal aging Methods 0.000 abstract description 2
- 238000010008 shearing Methods 0.000 abstract 1
- 239000013464 silicone adhesive Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 description 6
- 238000005273 aeration Methods 0.000 description 5
- 238000003760 magnetic stirring Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229910002808 Si–O–Si Inorganic materials 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000001257 hydrogen Chemical group 0.000 description 2
- 229910052739 hydrogen Chemical group 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 150000003961 organosilicon compounds Chemical class 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920003216 poly(methylphenylsiloxane) Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention belongs to the field of high polymer materials, and particularly relates to symmetrical tetraphenyl phenyl vinyl silicone oil and a preparation method thereof. The synthesized symmetrical tetraphenyl phenyl vinyl silicone oil is mainly used as a high-temperature-resistant auxiliary agent and an irradiation-resistant auxiliary agent of silicone rubber and silicone resin adhesives. When the silicon rubber is vulcanized, the symmetrical tetraphenyl phenyl vinyl silicone oil can participate in the cross-linking reaction of the silicon rubber and is bonded to a silicon rubber macromolecular chain, and the symmetrically distributed tetraphenyl phenyl groups have the functions of a nano-scale reinforcing phase and have stronger thermal deformation resistance, thermal aging resistance, high temperature resistance, irradiation resistance and solvent resistance; the symmetrical tetraphenyl phenyl vinyl silicone oil is used in silicone adhesive to raise the adhesive strength, shearing strength and high temperature resistance.
Description
Technical Field
The invention belongs to the field of high polymer materials, particularly relates to symmetrical tetraphenyl phenyl vinyl silicone oil and a preparation method thereof, and particularly relates to a method for synthesizing symmetrical tetraphenyl phenyl vinyl by using tetraphenylcyclopentadienone and polyvinyl silicone oil in a chloronaphthalene normal-pressure open system.
Background
The silicone oil is a linear structure oily substance formed by carrying out hydrolytic polycondensation on an organic silicon monomer with double functional groups or single functional groups, and is chain-shaped silicone oil with different polymerization degrees. The structural formula is as follows:
wherein n is the degree of polymerization, R is a hydrocarbon group such as methyl, ethyl, phenyl, etc., and X is hydroxyl or hydrogen. The other silicone oil is modified silicone oil, the molecular main chain is not completely composed of Si-O-Si bonds, and a certain amount of silicon heterochains are contained. We can classify them into two classes of linear silicone oils and modified silicone oils according to R, R'. Linear silicone oils include both non-functional and functional silicone oils; the modified silicone oil comprises three types of carbon functional silicone oil, copolymerized silicone oil and main chain modified silicone oil. The silicone oil (Wangchunjiang, Wangyang. production status and development trend of organosilicon compounds [ J ]. Jiangsu chemical industry, 2002,30(2): 16-21) is mainly a linear silicone oil using Si-O-Si as main chain, and the organosilicon compounds with low molecular weight or even high molecular weight and alkyl, aryl or active groups connected to silicon atoms have small intermolecular force and large distance, and the molecules are in spiral structures, so that the special structure endows the silicone oil with excellent characteristics, and the silicone oil is an important product in organosilicon high polymers. It is colorless, tasteless, nontoxic, nonvolatile, and non-corrosive silicone oil liquid oil with various viscosities, and has the dual properties of glass and quartz. Silicone oils have many specific properties due to their specific structure. Such as good heat resistance, water resistance, low viscosity-temperature coefficient, low surface tension, electrical insulation, oxygen resistance, physiological inertia, flexibility and the like, and has good surface activity and excellent film forming property (Wangduon. development and application progress of modified silicone oil [ J ] Shanghai Ma technology, 2012 (3): 21-26). The silicone oil is classified into methyl silicone oil, ethyl silicone oil, phenyl silicone oil, methyl hydrogen-containing silicone oil, methyl phenyl silicone oil, and the like according to chemical structures.
However, these conventional silicone oils cannot be used under special conditions, for example, under extreme conditions such as aerospace and nuclear industries, the silicone oils are required to have tetraphenyl or fused ring groups, and substances containing multiple benzene rings can absorb radiation energy of high-energy rays more easily, disperse the energy in a large conjugated system, and then emit the energy to the surrounding environment in the form of light and heat. Besides the functions, the uniformly distributed tetraphenyl groups have less influence on the performance protection and the process of a system due to the uniform distribution of the tetraphenyl groups, and have practical significance advantages.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention provides the symmetrical tetraphenyl phenyl vinyl silicone oil and the preparation method thereof, the tetraphenyl cyclopentadienone and the polyvinyl silicone oil are utilized to prepare the symmetrical tetraphenyl phenyl vinyl silicone oil in a normal-pressure open system of chloronaphthalene, and an auxiliary agent with excellent performance is provided for preparing high-temperature-resistant and irradiation-resistant silicone rubber or silicone resin adhesive.
In order to achieve the purpose, the invention adopts the following technical scheme.
The symmetrical tetraphenyl phenyl vinyl silicone oil comprises the following raw materials in parts by weight: 5-20 parts of tetraphenylcyclopentadienone, 20-50 parts of polyvinyl silicone oil, 1-5 parts of catalyst and 50-100 parts of solvent.
Further, the tetraphenylcyclopentadienone is purple particles, and is prepared by removing two molecules of water and one molecule of potassium hydroxide through the reaction of acenaphthenequinone and dibenzyl ketone.
Further, the solvent is one of xylene, toluene, chlorotoluene and dichlorotoluene.
Further, the polyvinyl silicone oil is polymethyl silicone oil with a vinyl content of 0.04mol/L-0.068 mol/L.
Further, the catalyst is one of alpha-chloronaphthalene and beta-chloronaphthalene.
A preparation method of symmetrical tetraphenyl phenyl vinyl silicone oil comprises the following steps:
step 1, adding tetraphenylcyclopentadienone and a solvent into a reactor, and magnetically stirring until the tetraphenylcyclopentadienone is dissolved.
And 2, adding polyvinyl silicone oil and a catalyst into the reactor, fully and uniformly stirring, introducing nitrogen into the system, opening a heating device, heating to 140-280 ℃ for continuous reaction, heating to 210-280 ℃ for continuous reaction for 8-15 hours when the color of the reaction system is changed from dark green to orange and transparent, and stopping the reaction.
And 3, cooling the product to a certain temperature, transferring the solution into a separating funnel, standing for layering, collecting an upper-layer product, washing the collected upper-layer transparent product with methanol, and carrying out reduced pressure distillation to remove methanol and redundant unreacted raw material polyvinyl silicone oil to obtain the symmetrical tetraphenyl phenyl vinyl silicone oil.
Further, the dissolving temperature in the step 1 is 50-105 ℃.
Further, the nitrogen velocity in the step 2 is 0.5-5 m/s.
Further, the cooling temperature in the step 3 is 20-30 ℃.
Compared with the prior art, the invention has the beneficial effects of.
1. The synthesis process is an open system and is carried out at normal pressure, which is favorable for the smooth implementation of the synthesis.
2. The synthesized symmetrical tetraphenyl phenyl vinyl silicone oil is mainly used as a high-temperature-resistant auxiliary agent and an irradiation-resistant auxiliary agent of silicone rubber and silicone resin adhesives. When the silicon rubber is vulcanized, the symmetrical tetraphenyl phenyl vinyl silicone oil can participate in the cross-linking reaction of the silicon rubber and is bonded to a silicon rubber macromolecular chain, and the symmetrically distributed tetraphenyl phenyl groups have the functions of a nano-scale reinforcing phase and have stronger thermal deformation resistance, thermal aging resistance, high temperature resistance, irradiation resistance and solvent resistance. The symmetrical tetraphenyl phenyl vinyl silicone oil can also be used in a silicone resin adhesive to improve the adhesive strength, the shear strength and the high temperature resistance of the adhesive.
Drawings
FIG. 1 is a flow chart of a preparation process of symmetrical tetraphenyl phenyl vinyl silicone oil.
FIG. 2 is an infrared spectrum of a symmetrical tetraphenyl phenyl vinyl silicone oil prepared in example 1.
FIG. 3 shows the nuclear magnetic spectrum of the symmetrical tetraphenyl phenyl vinyl silicone oil prepared in example 1.
FIG. 4 is a reaction mechanism diagram of the preparation of symmetrical tetraphenyl phenyl vinyl silicone oil.
Detailed Description
The following describes in detail specific embodiments of the present invention. It should be understood that the detailed description and specific examples, while indicating the present invention, are given by way of illustration and explanation only, not limitation.
Example 1.
Placing 5 parts of tetraphenylcyclopentadienone powder and 50 parts of dimethylbenzene into a 200ml three-necked bottle with a condensing reflux device, a magnetic stirring device and an aeration device, keeping the temperature at 50 ℃, heating to 75 ℃ after the tetraphenylcyclopentadienone is completely dissolved, slowly adding polyvinyl silicone oil (containing 0.04mol/L of vinyl) containing 20 parts into the system, stirring for 5min after the dropwise addition is finished, slowly dropwise adding 1 part of alpha-chloronaphthalene into the three-necked bottle within 20min, introducing nitrogen (the speed is 1 m/s), heating to 155 ℃ for continuous reaction, heating to 220 ℃ for continuous reaction for 15 hours when the color of the reaction system is changed into an orange transparent solution, stopping the reaction, slowly cooling the product to 20 ℃, placing the product into a separating funnel, standing for layering, collecting an upper layer product, washing the collected upper layer product with methanol to be transparent, carrying out reduced pressure distillation to remove the normethanol and unreacted polyvinyl silicone oil (containing 0.04mol/L of vinyl), the product was obtained as a clear oily liquid.
Example 2.
Placing 5 parts of tetraphenylcyclopentadienone powder and 60 parts of xylene into a 200ml three-necked bottle with a condensing reflux device, a magnetic stirring device and an aeration device, keeping the temperature at 50 ℃, heating to 85 ℃ after the tetraphenylcyclopentadienone is completely dissolved, slowly adding 25 parts of polyvinyl silicone oil (containing 0.04mol/L of vinyl) into the system, stirring for 5min after the dropwise addition is finished, slowly dropwise adding 1.5 parts of alpha-chloronaphthalene into the three-necked bottle within 20min, introducing nitrogen (the speed is 1.5 m/s), heating to 165 ℃ for continuous reaction, heating to 220 ℃ for continuous reaction for 15 hours when the color of the reaction system is changed into dark green transparent solution, stopping the reaction, slowly cooling the product to 20 ℃, placing the product into a separating funnel, standing for layering, collecting an upper layer product, washing the collected upper layer product with methanol to be transparent, and distilling under reduced pressure to remove the methanol and unreacted polyvinyl norsilicone oil (containing 0.04mol/L of vinyl), the product was obtained as a clear oily liquid.
Example 3.
Putting 10 parts of tetraphenylcyclopentadienone powder and 80 parts of xylene into a 200ml three-necked bottle with a condensing reflux device, a magnetic stirring device and an aeration device, keeping the temperature at 50 ℃, heating to 75 ℃ after the tetraphenylcyclopentadienone is completely dissolved, slowly adding polyvinyl silicone oil (containing 0.054mol/L of vinyl) containing 20 parts into the system, stirring for 5min after the dropwise addition is finished, slowly dropwise adding 2 parts of alpha-chloronaphthalene into the three-necked bottle within 30min, introducing nitrogen (the speed is 1.5 m/s), heating to 155 ℃ for continuous reaction, heating to 230 ℃ for continuous reaction for 10 hours when the color of the reaction system is changed into dark green transparent solution, stopping the reaction, slowly cooling the product to room temperature, placing the product into a separating funnel, standing for layering, collecting an upper layer product, washing the collected upper layer product with methanol to be transparent, and carrying out reduced pressure distillation to remove the polyvinyl norsilicone oil (containing 0.4 mol/L of vinyl) and unreacted polyvinyl silicone oil (containing 0.054mol/L of vinyl), the product was obtained as a clear oily liquid.
Example 4.
Putting 10 parts of tetraphenylcyclopentadienone powder and 90 parts of dimethylbenzene into a 200ml three-necked bottle with a condensing reflux device, a magnetic stirring device and an aeration device, keeping the temperature at 50 ℃, heating to 95 ℃ after the tetraphenylcyclopentadienone is completely dissolved, slowly adding polyvinyl silicone oil (containing 0.054mol/L of vinyl) containing 20 parts into the system, stirring for 5min after the dropwise addition is finished, slowly dropwise adding 3 parts of alpha-chloronaphthalene into the three-necked bottle within 30min, introducing nitrogen (the speed is 3 m/s), heating to 165 ℃ for continuous reaction, heating to 230 ℃ for continuous reaction for 10 hours when the color of the reaction system is changed into an orange transparent solution, stopping the reaction, slowly cooling the product to 20 ℃, placing the product into a separating funnel, standing for layering, collecting an upper layer product, washing the collected upper layer product with methanol to be transparent, carrying out reduced pressure distillation to remove the normethanol and unreacted polyvinyl silicone oil (containing 0.054mol/L of vinyl), the product was obtained as a clear oily liquid.
Example 5.
Placing 20 parts of tetraphenylcyclopentadienone powder and 100 parts of dimethylbenzene into a 200ml three-necked bottle with a condensing reflux device, a magnetic stirring device and an aeration device, keeping the temperature at 50 ℃, heating to 75 ℃ after the phenyltetracyclopentadienone is completely dissolved, slowly adding 45 parts of polyvinyl silicone oil (containing 0.068mol/L of vinyl) into the system, stirring for 5min after the dropwise addition is finished, slowly dropwise adding 5 parts of alpha-chloronaphthalene into the three-necked bottle within 30min, introducing nitrogen (the speed is 5 m/s), heating to 155 ℃ for continuous reaction, heating to 250 ℃ for continuous reaction for 8 hours when the black color of the reaction system is changed into a green transparent solution, stopping the reaction, slowly cooling the product to 20 ℃, placing the product into a separating funnel, standing for layering, collecting an upper layer product, washing the collected upper layer product with methanol to be transparent, and distilling under reduced pressure to remove the normethanol and unreacted polyvinyl silicone oil (containing 0.068mol/L of vinyl), the product was obtained as a clear oily liquid.
From FIG. 2, it can be seen that 1400-1600cm is obtained compared with the infrared spectrum of polyvinyl silicone oil-1The absorption peak of phenyl is increased in the region, and the tetraphenylcyclopentadienone is 1710cm-1The absorption peak at C = O disappeared, confirming the successful introduction of tetraphenylcyclopentadienone onto the vinyl group, confirming that the synthesis was the expected product.
As is clear from FIG. 3, part of the vinyl groups on the polyvinyl silicone oil were replaced with tetraphenyl groups, so that a proton peak was observed at a chemical shift of 6.8 to 7.6ppm, which was known as a proton peak of a phenyl group of a symmetrical tetraphenyl group, and the results of the infrared spectroscopy were consistent.
Claims (9)
1. The symmetrical tetraphenyl phenyl vinyl silicone oil is characterized by comprising the following raw materials in parts by weight: 5-20 parts of tetraphenylcyclopentadienone, 20-50 parts of polyvinyl silicone oil, 1-5 parts of catalyst and 50-100 parts of solvent.
2. The symmetrical tetraphenyl phenyl vinyl silicone oil of claim 1 wherein the tetraphenylcyclopentadienone is a purple colored particle made by reacting acenaphthenequinone with dibenzyl ketone to remove two molecules of water and one molecule of potassium hydroxide.
3. The symmetrical tetraphenyl phenyl vinyl silicone oil of claim 1 wherein the solvent is one of xylene, toluene, chlorotoluene, and dichlorotoluene.
4. The symmetrical tetraphenyl phenyl vinyl silicone oil according to claim 1, wherein said polyvinyl silicone oil is a polymethylsilicone oil having a vinyl group content of 0.04mol/L to 0.068 mol/L.
5. The symmetrical tetraphenyl phenyl vinyl silicone oil of claim 1 wherein the catalyst is one of alpha-chloronaphthalene and beta-chloronaphthalene.
6. A preparation method of symmetrical tetraphenyl phenyl vinyl silicone oil is characterized by comprising the following steps:
step 1, adding tetraphenylcyclopentadienone and a solvent into a reactor, and magnetically stirring until the tetraphenylcyclopentadienone is dissolved;
step 2, adding polyvinyl silicone oil and a catalyst into the reactor, fully and uniformly stirring, introducing nitrogen into the system, opening a heating device, heating to 140-280 ℃ for continuous reaction, heating to 210-280 ℃ for continuous reaction for 8-15 hours when the color of the reaction system is changed from dark green to orange and transparent, and stopping the reaction;
and 3, cooling the product to a certain temperature, transferring the solution into a separating funnel, standing for layering, collecting an upper-layer product, washing the collected upper-layer transparent product with methanol, and carrying out reduced pressure distillation to remove methanol and redundant unreacted raw material polyvinyl silicone oil to obtain the symmetrical tetraphenyl phenyl vinyl silicone oil.
7. The method for preparing symmetrical tetraphenyl phenyl vinyl silicone oil according to claim 6 wherein the dissolution temperature in step 1 is 50-105 ℃.
8. The method for preparing symmetrical tetraphenyl phenyl vinyl silicone oil according to claim 6 wherein the nitrogen rate in step 2 is 0.5-5 m/s.
9. The method for preparing symmetrical tetraphenyl phenyl vinyl silicone oil according to claim 6 wherein the cooling temperature in step 3 is 20-30 ℃.
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| CN115073745A (en) * | 2022-07-01 | 2022-09-20 | 安徽恒光聚氨酯材料有限公司 | Novel environment-friendly antioxidant modified silicone oil and preparation method thereof |
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| CN105859767A (en) * | 2016-03-30 | 2016-08-17 | 沈阳化工大学 | Normal pressure synthetic method for polyphenyl cyclic siloxane containing three vinyl groups |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105859767A (en) * | 2016-03-30 | 2016-08-17 | 沈阳化工大学 | Normal pressure synthetic method for polyphenyl cyclic siloxane containing three vinyl groups |
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| 史保川等: ""一类含多苯基芳基硅烷偶联剂的合成及应用"", 《南京师大学报（自然科学版）》 * |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115073745A (en) * | 2022-07-01 | 2022-09-20 | 安徽恒光聚氨酯材料有限公司 | Novel environment-friendly antioxidant modified silicone oil and preparation method thereof |
| CN115073745B (en) * | 2022-07-01 | 2023-09-15 | 安徽恒光聚氨酯材料有限公司 | Environment-friendly antioxidant modified silicone oil and preparation method thereof |
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Application publication date: 20211126 |