CN102617630B - Cage type oligomerization octa-propargyl amine phenyl silsesquioxane and preparation method thereof - Google Patents

Cage type oligomerization octa-propargyl amine phenyl silsesquioxane and preparation method thereof Download PDF

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CN102617630B
CN102617630B CN201210065173.2A CN201210065173A CN102617630B CN 102617630 B CN102617630 B CN 102617630B CN 201210065173 A CN201210065173 A CN 201210065173A CN 102617630 B CN102617630 B CN 102617630B
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propargyl amine
aminophenyl
filter cake
phenylsilsesquioxane
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CN102617630A (en
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杨荣杰
范海波
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Beijing Institute of Technology BIT
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Abstract

The invention relates to cage type oligomerization octa-propargyl amine phenyl silsesquioxane and a preparation method thereof, and belongs to the technical field of nano materials. The method comprises the following steps of: adding octa-amino phenyl silsesquioxane and a solvent into a reactor, adding an alkali compound, and dripping an allylene bromine solution to obtain a reaction solution; filtering, adding a filtrate into a precipitant, and filtering to obtain a filter cake; dissolving the filter cake in the solvent, washing by using a saline solution, adding an organic layer into the precipitant, filtering, and drying the filter cake to obtain the cage type oligomerization octa-propargyl amine phenyl silsesquioxane. The method has the advantages of mild and stable reaction condition, high repeatability and yield, short period and the like, and is suitable for expansive production.

Description

A kind of polyhedral oligomeric eight propargyl amine phenylsilsesquioxane and preparation method thereof
Technical field
The present invention relates to a kind of polyhedral oligomeric eight propargyl amine phenylsilsesquioxane (OPAPS) and preparation method thereof, belong to technical field of nano material.
Background technology
Silicon-containing polymer generally has excellent thermotolerance, resistance to water soak and good dielectric properties.Polyhedral oligomeric silsesquioxane (POSS) forms inner inorganic skeleton by Si, O, and be externally connected to the nanoscale three-dimensional structural system of machine group, molecule mostly is cage structure, and its organic substituent can be inertia organic group or active function groups.The inorganic interior nuclear energy that POSS molecule Midst density is larger suppresses the chain movement of polymer molecule and gives hybrid material good resistance toheat, corresponding organic substituent and macromolecular chain then give the good toughness of hybrid material and workability, make material have the essential characteristic of organic polymer and inorganic ceramic simultaneously, be therefore called as high-performance polymer material of new generation.Therefore, the numerous areas such as high temperature resistant at polymkeric substance, fire-retardant, the printing of POSS, electrochemistry have a wide range of applications.
Polyacetylene based polyalcohol is the high-performance polymer of a class by the monomer polymerization containing polyacetylene group, and its principal feature is: polymerization process is a kind of polyaddition reaction, non-volatile thing and the effusion of low molecule quality by product during solidification; Usually in highly cross-linked structure after resin solidification, resistance to elevated temperatures is very excellent; Pyrolysis charring rate is high, and shrinking percentage is lower; Prepolymer is in a liquid state or easy to be molten meltable solid-state, is convenient to composite material forming processing.These features show that polyacetylene based polyalcohol has broad application prospects in high-tech sector.
Eight propargyl amine phenylsilsesquioxane, as the novel POSS nano material of one, have good chemical reactivity and thermotolerance.
Summary of the invention
The object of the invention is to propose a kind of polyhedral oligomeric eight propargyl amine phenylsilsesquioxane and preparation method thereof, polyhedral oligomeric eight propargyl amine phenylsilsesquioxane, it is a kind of novel oligomer silasesquioxanes nano material containing multiple end alkynyl radical, simultaneously containing silicon, nitrogen element, there is with it constructional feature of POSS and end alkynyl radical, there is high temperature resistant, fire-retardant, effect such as raising dielectric properties and mechanical property etc. in polymer composites.
The object of the invention is to be achieved through the following technical solutions.
A kind of polyhedral oligomeric eight propargyl amine phenylsilsesquioxane of the present invention, its molecular formula is (SiO 1.5c 9nH 8) 8, its structural formula is:
Wherein, R=NHCH 2cCH.
The preparation method of a kind of polyhedral oligomeric eight propargyl amine phenylsilsesquioxane of the present invention, its concrete preparation process is as follows:
1) eight aminophenyl silicious sesquioxanes and solvent C are joined in the reactor with condensation reflux unit, temperature regulating device, protection of inert gas and magnetic stirring apparatus, stir, the temperature controlling reactor is 20 ~ 120 DEG C, add basic cpd, then propine bromine solutions is dripped, reaction times is 4 ~ 36 hours, obtains reaction solution;
2) by step 1) reacting liquid filtering that obtains, filtrate joins in precipitation agent A, filters, obtains filter cake;
3) by step 2) filter cake that obtains is dissolved in solvent D, and then use brine It 3 ~ 5 times, then organic layer is joined in precipitation agent B, filter, dried by filter cake, the bake out temperature of filter cake is 40 ~ 140 DEG C, finally obtains polyhedral oligomeric eight propargyl amine phenylsilsesquioxane;
Above-mentioned steps 1) in solvent C be C 1~ C 3alcohol, acetone, acetonitrile, methylene dichloride, trichloromethane, benzene,toluene,xylene, dioxane, tetrahydrofuran (THF), ethyl acetate, pyridine, dimethyl formamide, one in N,N-DIMETHYLACETAMIDE or its mixture, be preferably dimethyl formamide; The ratio of eight aminophenyl silicious sesquioxanes and solvent is 1g: 1 ~ 50mL;
Above-mentioned steps 1) in rare gas element be nitrogen or argon gas;
Above-mentioned steps 1) neutral and alkali compound is one in sodium hydroxide, potassium hydroxide, magnesium hydroxide, aluminium hydroxide, sodium bicarbonate, saleratus, triethylamine, potassium tert.-butoxide or its mixture, is preferably sodium hydroxide or triethylamine;
Above-mentioned steps 1) in the solvent E of propine bromine solutions be C 1~ C 3alcohol, acetone, acetonitrile, methylene dichloride, trichloromethane, benzene,toluene,xylene, dioxane, tetrahydrofuran (THF), ethyl acetate, pyridine, dimethyl formamide, one in N,N-DIMETHYLACETAMIDE or its mixture, be preferably toluene; The solubility massfraction of propine bromine solutions is 20% ~ 95%;
Above-mentioned steps 1) in eight aminophenyl silicious sesquioxanes and basic cpd mole ratio be 1: 5 ~ 100;
Above-mentioned steps 1) in eight aminophenyl silicious sesquioxanes and the propine bromine in propine bromine solutions mole ratio be 5 ~ 100;
Above-mentioned steps 2) in precipitation agent A be one in normal hexane, normal heptane, sherwood oil, benzene,toluene,xylene, deionized water, hexanaphthene or its mixture, be preferably deionized water;
Above-mentioned steps 2) in the volume of filtrate and the volume ratio of precipitation agent be 1: 1 ~ 20;
Above-mentioned steps 3) in solvent D be C 1~ C 3alcohol, acetone, acetonitrile, methylene dichloride, trichloromethane, benzene,toluene,xylene, dioxane, tetrahydrofuran (THF), ethyl acetate, pyridine, dimethyl formamide, one in N,N-DIMETHYLACETAMIDE or its mixture, solvent is preferably tetrahydrofuran (THF);
Above-mentioned steps 3) in the ratio of filter cake and solvent D be 1g: 1 ~ 50mL;
Above-mentioned steps 3) in precipitation agent B be one in normal hexane, normal heptane, sherwood oil, benzene,toluene,xylene, deionized water, hexanaphthene or its mixture, be preferably normal hexane;
Above-mentioned steps 3) in the volume of organic layer and the volume ratio of precipitation agent be 1: 1 ~ 20.
Polyhedral oligomeric eight propargyl amine phenylsilsesquioxane is the polyhedral oligomeric silsesquioxane containing eight propargyl amine phenyl, it is a kind of three-dimensional cage modle hybrid inorganic-organic materials with nano-scale, can add in polymkeric substance by methods such as interpolation, grafting, crosslinked or copolymerization, the multiple performances such as high temperature resistant, fire-retardant, mechanics, the dielectric properties of polymkeric substance can be improved.
Beneficial effect
The features such as reaction conditions gentleness of the present invention is stable, reproducible, productive rate is high, the cycle is short, are applicable to expansion property and produce.
Accompanying drawing explanation
Fig. 1 is eight aminophenyl silicious sesquioxane FT-IR spectrograms prepared by embodiment 1;
Fig. 2 is eight aminophenyl silicious sesquioxanes prepared by embodiment 1 1h NMR spectrogram;
Fig. 3 is eight aminophenyl silicious sesquioxane XRD spectra prepared by embodiment 1.
Embodiment
Below by embodiment, the invention will be further described, but embodiment does not limit the scope of the invention.
Embodiment 1
1) 0.5g eight aminophenyl silicious sesquioxane and 10mL dimethyl formamide are joined in the 100mL there-necked flask of band reflux condensing tube, constant pressure funnel, temperature regulating device, argon shield and magnetic agitation, stir, temperature is 80 DEG C, add 0.425g triethylamine, then the toluene solution 2.4g of massfraction 80% propine bromine is dripped, react 24 hours, obtain reaction solution;
2) by step 1) reacting liquid filtering that obtains, filtrate joins in 40mL deionized water, filters, obtains filter cake;
3) by step 2) filter cake that obtains is dissolved in 10mL tetrahydrofuran (THF), solution is placed in taper separating funnel, then 40mL brine It is used 3 times, then organic layer is joined in 60mL normal hexane, separate out tan precipitate, throw out to be put in 60 DEG C of vacuum drying ovens dry 20 hours, finally obtain polyhedral oligomeric eight propargyl amine phenylsilsesquioxane, productive rate is 74.8%; Fig. 1 is the FT-IR spectrogram of eight propargyl amine phenylsilsesquioxane, 3358 and 3456cm -1the vibration peak completely dissolve of place's primary amine groups, along with the appearance of end alkynyl radical, 3288,1697 and 642cm -1occur three distinctive absorption peaks of end alkynyl radical, meanwhile, primary amine changes secondary amine into, 3375cm -1place is the absorption peak of secondary amine, 1115cm -1for the absorption peak of Si-O-Si key.Fig. 2 is eight propargyl amine phenylsilsesquioxane 1h NMR spectrogram, at eight aminophenyl silicious sesquioxanes 1in H NMR spectrogram, 4.5 ~ 5.4ppm place is-NH 2the vibration peak of middle Hydrogen Proton, and at eight propargyl amine phenylsilsesquioxane 1in H NMR spectrogram, peak completely dissolve herein, the substitute is the resonance peak of 4.1ppm place-NH-, 3.9ppm place-CH 2-resonance peak and the resonance peak of 3.0ppm place-C ≡ CH.
Wherein spectral data is:
FT-IR(KBr，cm -1)：3288，1697and?642(-C≡CH)，3375(-NH-)，1115(Si-O-Si)； 1H?NMR(DMSO-d 6，δ，ppm，TMS)：7.9-6.5(Ar，3.81H)，4.2-4(-NH-，0.54H)，4-3.5(-CH2-，1.84H)，3.1-2.8(-C≡CH，1.00H). 29Si?solid?NMR(δ，ppm)：-77.9(Si?atoms?connected?to?phenyl?group).
Fig. 3 is the XRD spectra of eight aminophenyl silicious sesquioxanes, and 2 θ=6.45 ° are the diffraction peak of its POSS cagelike structure.Calculate cage according to Bragg equation and be of a size of 1.37nm, prove that it has the three-dimensional structure of nano-scale.
Embodiment 2
1) 2.5g eight aminophenyl silicious sesquioxane and 40mL dimethyl formamide are joined in the 250mL there-necked flask of band reflux condensing tube, constant pressure funnel, temperature regulating device, argon shield and magnetic agitation, stir, temperature is 80 DEG C, add 2.231g triethylamine, then the toluene solution 7.8g of massfraction 80% propine bromine is dripped, react 24 hours, obtain reaction solution;
2) by step 1) reacting liquid filtering that obtains, filtrate joins in 200mL deionized water, filters, obtains filter cake;
3) by step 2) filter cake that obtains is dissolved in 40mL tetrahydrofuran (THF), solution is placed in taper separating funnel, then 200mL brine It is used 4 times, then organic layer is joined in 200mL normal hexane, separate out tan precipitate, throw out to be put in 80 DEG C of vacuum drying ovens dry 15 hours, finally obtain polyhedral oligomeric eight propargyl amine phenylsilsesquioxane, productive rate is 76.4%.
Embodiment 3
1) 2.5g eight aminophenyl silicious sesquioxane and 40mL dimethyl formamide are joined in the 100mL there-necked flask of band reflux condensing tube, constant pressure funnel, temperature regulating device, argon shield and magnetic agitation, stir, temperature is 80 DEG C, add 1.4g sodium hydroxide, then the toluene solution 8.2g of massfraction 80% propine bromine is dripped, react 20 hours, obtain reaction solution;
2) by step 1) reacting liquid filtering that obtains, filtrate joins in 200mL deionized water, filters, obtains filter cake;
3) by step 2) filter cake that obtains is dissolved in 40mL tetrahydrofuran (THF), solution is placed in taper separating funnel, then 180mL brine It is used 4 times, then organic layer is joined in 240mL normal hexane, separate out tan precipitate, throw out to be put in 60 DEG C of vacuum drying ovens dry 20 hours, finally obtain polyhedral oligomeric eight propargyl amine phenylsilsesquioxane, productive rate is 74.2%.
Embodiment 4
1) 7.5g eight aminophenyl silicious sesquioxane and 60mL dimethyl formamide are joined in the 250mL there-necked flask of band reflux condensing tube, constant pressure funnel, temperature regulating device, argon shield and magnetic agitation, stir, temperature is 80 DEG C, add 4.2g sodium hydroxide, then the toluene solution 23.4g of massfraction 80% propine bromine is dripped, react 26 hours, obtain reaction solution;
2) by step 1) reacting liquid filtering that obtains, filtrate joins in 300mL deionized water, filters, obtains filter cake;
3) by step 2) filter cake that obtains is dissolved in 100mL tetrahydrofuran (THF), solution is placed in taper separating funnel, then 400mL brine It is used 3 times, then organic layer is joined in 400mL normal hexane, separate out tan precipitate, throw out to be put in 60 DEG C of vacuum drying ovens dry 20 hours, finally obtain polyhedral oligomeric eight propargyl amine phenylsilsesquioxane, productive rate is 72.7%.
Embodiment 5
1) 7.5g eight aminophenyl silicious sesquioxane and 60mL dimethyl formamide are joined in the 250mL there-necked flask of band reflux condensing tube, constant pressure funnel, temperature regulating device, argon shield and magnetic agitation, stir, temperature is 80 DEG C, add 6.693g triethylamine, then the toluene solution 24.0g of massfraction 80% propine bromine is dripped, react 24 hours, obtain reaction solution;
2) by step 1) reacting liquid filtering that obtains, filtrate joins in 300mL deionized water, filters, obtains filter cake;
3) by step 2) filter cake that obtains is dissolved in 80mL tetrahydrofuran (THF), solution is placed in taper separating funnel, then 500mL brine It is used 5 times, then organic layer is joined in 400mL normal hexane, separate out tan precipitate, throw out to be put in 60 DEG C of vacuum drying ovens dry 20 hours, finally obtain polyhedral oligomeric eight propargyl amine phenylsilsesquioxane, productive rate is 73.5%.

Claims (4)

1. a polyhedral oligomeric eight propargyl amine phenylsilsesquioxane, is characterized in that: its molecular formula is (SiO 1.5c 9nH 8) 8, its structural formula is:
Wherein, R=NHCH 2cCH.
2. a preparation method for polyhedral oligomeric eight propargyl amine phenylsilsesquioxane, is characterized in that: concrete preparation process is as follows:
1) eight aminophenyl silicious sesquioxanes and solvent dimethylformamide are joined in the reactor with condensation reflux unit, temperature regulating device, protection of inert gas and magnetic stirring apparatus, stir, the temperature controlling reactor is 80 DEG C, add basic cpd triethylamine, then the toluene solution of the propine bromine of massfraction 80% is dripped, reaction times is 20 ~ 26 hours, obtains reaction solution;
2) by step 1) reacting liquid filtering that obtains, filtrate joins in precipitation agent deionized water, filters, obtains filter cake;
3) by step 2) filter cake that obtains is dissolved in solvents tetrahydrofurane, with brine It 3 ~ 5 times, then organic layer is joined in precipitation agent normal hexane, filter, filter cake is dried, the bake out temperature of filter cake is 60 ~ 80 DEG C, finally obtains polyhedral oligomeric eight propargyl amine phenylsilsesquioxane;
Above-mentioned steps 1) ratio of eight aminophenyl silicious sesquioxanes and solvent dimethylformamide is 1g:8 ~ 20mL;
Above-mentioned steps 1) in eight aminophenyl silicious sesquioxanes and basic cpd triethylamine mole ratio be 1:10;
Above-mentioned steps 1) in the mass ratio of toluene solution of eight aminophenyl silicious sesquioxanes and propine bromine be 1:3.12 ~ 4.8;
Above-mentioned steps 2) in the volume of precipitation agent and step 1) in the volume ratio of solution dimethyl formamide be 1:4 ~ 5;
Above-mentioned steps 3) in the ratio of solvents tetrahydrofurane and raw material eight aminophenyl silicious sesquioxane be 10.7 ~ 20mL:1g;
Above-mentioned steps 3) in the volume of solvents tetrahydrofurane and the volume ratio of precipitation agent normal hexane be 1:4 ~ 6.
3. the preparation method of a kind of polyhedral oligomeric eight propargyl amine phenylsilsesquioxane according to claim 2, is characterized in that: step 1) in rare gas element be nitrogen or argon gas.
4. the preparation method of a kind of polyhedral oligomeric eight propargyl amine phenylsilsesquioxane according to claim 2, it is characterized in that: step 1) neutral and alkali compound triethylamine is when replacing with basic cpd sodium hydroxide, eight aminophenyl silicious sesquioxanes and basic cpd sodium hydroxide mole ratio be 1:16.
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JP2007182528A (en) * 2005-12-07 2007-07-19 Chisso Corp Polymer obtained by reacting silsesquioxane derivative and method for producing the same

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CN101503420A (en) * 2009-03-20 2009-08-12 北京化工大学 Octa-epoxy cage type sesquialter siloxane and preparation thereof

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Title
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Synthesis and Characterization of Organic/Inorganic Hybrid Star Polymers of 2,2,3,4,4,4-Hexafluorobutyl Methacrylate and Octa(aminophenyl)silsesquioxane Nano-Cage Made via Atom Transfer Radical Polymerization;H.HUSSAIN等;《Journal of Polymer Science: Part A: Polymer Chemistry》;20081009;第46卷(第22期);第7288页左栏第2段第22-33行、第7288页右栏最后一段至第7289页左栏第一段、第7288页右栏最后1段第2、3、9行、第7288页右栏最后1段第2行、第7288页右栏最后1段第4行、对比文件1第7288页右栏最后1段第2行、第7289页左栏第1段第4-5行 *

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