CN104262382A - Preparation method of ureido silane coupling agent - Google Patents
Preparation method of ureido silane coupling agent Download PDFInfo
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- CN104262382A CN104262382A CN201410458010.XA CN201410458010A CN104262382A CN 104262382 A CN104262382 A CN 104262382A CN 201410458010 A CN201410458010 A CN 201410458010A CN 104262382 A CN104262382 A CN 104262382A
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Abstract
The invention discloses a preparation method of a ureido silane coupling agent. The preparation method comprises the step of: by taking urea and an amino silane coupling agent as raw materials, in presence or absence of a solvent, reacting at a certain temperature in a nitrogen flow to directly obtain the ureido silane coupling agent. The preparation method of the ureido silane coupling agent is low in cost, high in product purity, simple in technology, mild in conditions and easy to operate, and thus is applicable to industrial production.
Description
Technical field
The present invention relates to the field of chemical synthesis, be specifically related to a kind of preparation method of ureido silane coupling agent.
Background technology
Silane coupling agent be a class in the molecule between simultaneously containing the silicoorganic compound of two kinds of different chemical character groups, it is used in glass filament reinforced plastics as the surface treatment agent of glass fibre at first.Discovery allyltriethoxysilane process glass fibre such as nineteen forty-seven Ralph K W and the polyester composite made can obtain double intensity, so far, have started the research and development of silane coupling agent.Use silane coupling agent in the composite, their mechanical property, electric property, weathering resistance, water tolerance, flame retardancy, cohesiveness, dispersiveness, formability and process operability etc. can be improved significantly.
Urea groups series silane coupling agent, it is neutral water-soluble cpds, and the reactive behavior at low temperatures with many resins all decreases, thus keeps certain maximal work performance.Compared with traditional similar auxiliary chemicals, it have use safety, reaction temperature and, bonding force is strong, the features such as adhesive property is good.Therefore, it is widely used in various chemical building material and tackiness agent, is used for plastics and rubber item mainly as additive, strengthens the bonding force between mineral filler and organic matrix.
The synthesis of urea groups series silane coupling agent is domestic there is not yet bibliographical information.Patent No. JPS5657792A disclose with containing the silanes of isocyanic ester and ammonia or amino-complex for raw material reaction preparation is containing the method for the silicoorganic compound of urea groups.But the method need use the expensive silicoorganic compound containing isocyanide ester, and severe reaction conditions in preparation process, need the conditions such as anhydrous, low temperature or pressurization, and the method side reaction is many, higher to equipment requirements, is unfavorable for suitability for industrialized production.Patent No. EP0276860 disclose with containing amino silicoorganic compound with carbamate for raw material reacts the method prepared and contain urea groups silicoorganic compound under the effect of catalyzer.But this technique exists catalyst residue, residual catalyzer itself easily affects the application of product, is unfavorable for the popularization of product; And due under ureido silane coupling agent normal temperature be wax-like, boiling point is high, product aftertreatment is as very difficult in method of purification, is difficult to obtain high purity product.Patent No. JPH08333375 discloses with aminosilane and urea as raw material prepares the method for ureido silane coupling agent under the effect of organotin catalysts, but also there is the problem of catalyst residue in this technique, the product purity that the method is obtained is simultaneously not high, does not utilize the application of this product.In addition, the organotin catalysts toxicity that this patent uses is very high, and it can destroy the protein of sulfur-bearing.For the restriction of organo-tin compound, before European Union, 89/677/EEC, 1999/51/EC and 2002/62/EC are crossed in successively issue.
The purity containing ureido silane coupling agent provided on the market at present, mostly about 95%, cannot meet the demand of high-end market.
Summary of the invention
[technical problem that will solve]
The object of the invention is the preparation method providing a kind of high purity ureido silane coupling agent for the deficiencies in the prior art, the method technique is simple, and easy to operate, be suitable for industrialized production, the ureido silane coupling agent purity obtained can reach 99%.
[technical scheme]
In order to reach above-mentioned technique effect, the present invention takes following technical scheme:
The chemical equation of ureido silane coupling agent of the present invention is as follows:
Or
Wherein
R1 represents the alkyl of 1-6 carbon atom;
R2, R3 represent 1-6 carbon atom alkyl or alkoxyl group.
A preparation method for ureido silane coupling agent, the method comprises the following steps:
A, mixing
Ratio 0.8 ~ the 1.5:1 pre-dry urea and amino silicane coupling agent being pressed amount of substance mixes, and is then dissolved in solvent by the mass ratio 0 ~ 200:100 of solvent and amino silicane coupling agent, obtains a kind of mixture;
B, nucleophilic substitution reaction
The mixture of steps A being heated to temperature is 100 ~ 150 DEG C, reaction 1 ~ 8h; Use nitrogen at the following bubbling of liquid level, and to control nitrogen gas stream flow velocity be 0.5 ~ 1.9mL/min simultaneously; Obtain a kind of reactant;
C, aftertreatment
The reactant of cooling step B, then low-boiling-point substance is removed in decompression.
According to a preferred embodiment of the present invention, in step, described amino silicane coupling agent is selected from aminopropyl trimethoxysilane, aminopropyl triethoxysilane, N-(β-aminoethyl)-γ-aminopropyltrimethoxysilane, N-(β-aminoethyl)-γ-aminopropyl triethoxysilane, N-(β-aminoethyl)-γ-aminopropyltriethoxy dimethoxysilane or N-(β-aminoethyl)-γ-aminopropyltriethoxy diethoxy silane.
According in another preferred embodiment of the present invention, in step, described solvent is that one or more are selected from the solvent of methyl alcohol, ethanol, tetrahydrofuran (THF), tetracol phenixin, benzene, dimethylbenzene, DMF, methyl-sulphoxide or N-Methyl pyrrolidone.
According in another preferred embodiment of the present invention, in step, described solvent and the mass ratio of amino silicane coupling agent are 0:100.
According in another preferred embodiment of the present invention, in stepb, it is 120 ~ 140 DEG C that mixture is heated to temperature, reaction 2 ~ 6h.
According in another preferred embodiment of the present invention, in stepb, described nitrogen gas stream flow velocity is 0.8 ~ 1.5mL/min.
According in another preferred embodiment of the present invention, in step C, described cooling cools the temperature to 50 ~ 100 DEG C.
According in another preferred embodiment of the present invention, in step C, described decompression is that to be evacuated to vacuum tightness be 50 ~ 150Pa.
The present invention will be explained below.
A preparation method for ureido silane coupling agent, the method comprises the following steps:
A, mixing
Ratio 0.8 ~ the 1.5:1 pre-dry urea and amino silicane coupling agent being pressed amount of substance mixes, and is then dissolved in solvent by the mass ratio 0 ~ 200:100 of solvent and amino silicane coupling agent, obtains a kind of mixture;
Meet water due to silane coupling agent can be polymerized, therefore, need urea and amino silicane coupling agent dry rear mixing in advance.
B, nucleophilic substitution reaction
The mixture of steps A being heated to temperature is 100 ~ 150 DEG C, reaction 1 ~ 8h; Use nitrogen at the following bubbling of liquid level, and to control nitrogen gas stream flow velocity be 0.5 ~ 1.9mL/min simultaneously; Obtain a kind of reactant;
Nucleophilic substitution reaction refers to the reaction that certain atom of being connected with carbon in organic molecule or group are replaced by certain atom or the group as nucleophilic reagent.In reaction process, substituted radical provides the pair of electrons forming new key, and the group be substituted then is left away with the pair of electrons of old key.
From the chemical equation of ureido silane coupling agent of the present invention
Or
Can find out, the group be substituted of the present invention is NH
2 -, this group is substituted rear generation ammonia.The object that nitrogen is led in the present invention has 2 points, and one is remove the air in reaction vessel, avoids such as the impacts such as oxygen of the composition in air to react; Two is utilize nitrogen to be overflowed from system by the ammonia of generation, can promote that reaction is carried out to the right, improve the speed of reaction; Avoid ammonia in reaction solution, generate corrosion-prone chemical substance, impact reaction and conversion unit simultaneously.
C, aftertreatment
The reactant of cooling step B, then low-boiling-point substance is removed in decompression.
Low-boiling-point substance refers to that boiling point is lower than the low boiling mixture of 40 DEG C.Organism of being everlasting is produced in producing, and its component is many, and boiling point is close and be difficult to be separated thus cause and can not well utilize.The polarity of general low-boiling-point substance component and product and the difference of physico-chemical property, can reach with the capillary chromatographic column of special stationary phase the effect be separated by selecting suitable polarity.
The raw material that low-boiling-point substance of the present invention mainly refers to ammonia and do not react on a small quantity.
According to another preferred embodiment of the present invention, described amino silicane coupling agent is selected from aminopropyl trimethoxysilane, aminopropyl triethoxysilane, N-(β-aminoethyl)-γ-aminopropyltrimethoxysilane, N-(β-aminoethyl)-γ-aminopropyl triethoxysilane, N-(β-aminoethyl)-γ-aminopropyltriethoxy dimethoxysilane or N-(β-aminoethyl)-γ-aminopropyltriethoxy diethoxy silane.
The molecular formula of described amino silicane coupling agent is NH
2(R1) Si (R3)
3or NH
2(R1) NH (R1) Si (R3)
3.Wherein R1 represents the alkyl of 1-6 carbon atom; R2, R3 represent 1-6 carbon atom alkyl or alkoxyl group.
According to another preferred embodiment of the present invention, described solvent is that one or more are selected from the solvent of methyl alcohol, ethanol, tetrahydrofuran (THF), tetracol phenixin, benzene, dimethylbenzene, DMF, methyl-sulphoxide or N-Methyl pyrrolidone.
Because urea of the present invention is solid, can not dissolve each other with amino silicane coupling agent, therefore need the solvent utilizing energy dissolved urea and amino silicane coupling agent, urea and amino silicane coupling agent are mixed fully.
Solvent object of the present invention is that urea is dissolved in silane coupling agent, thus forms homogeneous phase when making reaction.The solvent at this place is chosen as polar solvent.
According in another preferred embodiment of the present invention, in step, described solvent and the mass ratio of amino silicane coupling agent are 0:100.
Because the main purpose adding solvent is to make urea and amino silicane coupling agent dissolve, mixing; But after adding solvent, the boiling point of reaction can not improve, the carrying out of impact reaction; Therefore, the present invention, when removing solvent, selects suitable temperature of reaction, when temperature of reaction arrives certain temperature spot, urea can be impelled to dissolve, and ensures that urea mixes mutually with amino silicane coupling agent.
According to another preferred embodiment of the present invention, the temperature of described nucleophilic substitution reaction is 120 ~ 140 DEG C, and the reaction times is 2 ~ 6h.
When nucleophilic substitution reaction temperature of the present invention is too low, reaction is easily caused not carry out; Temperature is too high, can produce by product, reduces product purity.Therefore, suitable temperature can ensure that the carrying out reacted can obtain again the product of higher degree.
According to another preferred embodiment of the present invention, described nitrogen gas stream flow velocity is 0.8 ~ 1.5mL/min.
Nitrogen gas stream flow velocity of the present invention is too low, then Ammonia valatilization is slow, and speed of response reduces; Nitrogen gas stream flow velocity is too high, then, while wasting nitrogen, too increase the danger of material spray.Select suitable nitrogen gas stream flow velocity, can control best speed of response, thus ensure that raw material fully reacts, reacted product purity is high.
According in another preferred embodiment of the present invention, in step C, described cooling cools the temperature to 50 ~ 100 DEG C.
When the object that reactant cools is and avoids vacuumizing, product is extracted out.
According in another preferred embodiment of the present invention, in step C, described decompression is that to be evacuated to vacuum tightness be 50 ~ 150Pa.
Be in the gas rarefied content under vacuum state, usually represent by vacuum tightness.Vacuum values indicates the numerical value of system pressure actual numerical value lower than atmospheric pressure, that is: vacuum tightness=atmospheric pressure-pounds per square inch absolute (psia), pounds per square inch absolute (psia)=normal atmosphere+gauge pressure.
Because prior art has the use of catalyzer, post catalyst reaction remains, and affects the application of product; Simultaneously because there is catalyzer, also have impact on the purity of product, be unfavorable for applying of product.The present invention compared with prior art, does not use catalyzer, but, amino silicane coupling agent itself has catalytic, can make catalyzer in the polymerization of phenolic aldehyde, urea aldehyde, melamino-formaldehyde, amino silicane coupling agent self just can catalyzed reaction carry out, and does not have the problem of catalyst residue.
[beneficial effect]
The present invention compared with prior art, has following beneficial effect:
1, the raw material that preparation method of the present invention uses is simple and easy to get, and because can not use catalysts and solvents, because this reducing production cost, solving the residue problem of catalyzer, expanding the application of product;
2, the product purity that preparation method of the present invention obtains is high, and it reaches as high as 99%, is the index of 95% considerably beyond this product purity external;
3, preparation method's aftertreatment of the present invention is simple, only needs the ammonia of generation to get rid of, has greatly saved the consumption in production process, improve production efficiency;
4, preparation method's transformation efficiency of the present invention is high, reaches as high as 99.3%; Product purity is high and simple to operate, cost is low, is suitable for suitability for industrialized production.
Embodiment
Below in conjunction with embodiments of the invention, the invention will be further elaborated.
Embodiment 1:
0.460mol urea is added in the there-necked flask of band prolong that 250ml does, thermometer, then add 0.452mol aminopropyl triethoxysilane; Then be use N under the condition of 1.4mL/min at flow velocity
2at the following bubbling of liquid level, and warm at 130 DEG C of insulation reaction 2h in controlling; Then be cooled to 65 DEG C, be evacuated to vacuum tightness 95Pa, keep 1h except ammonia, afterwards again with N
2after sweeping de-30min, cooling sealing is preserved.Obtain colourless high viscosity oily matter, nuclear-magnetism detects purity 96%, and transformation efficiency is 96.5%.White waxy solid product is become after temperature cooling.
Embodiment 2:
Added by 0.452mol urea in the there-necked flask of band prolong that 250ml does, thermometer, then adding 0.452molN-(β-aminoethyl)-γ-aminopropyltrimethoxysilane, is then use N under the condition of 1.3mL/min at flow velocity
2at the following bubbling of liquid level, and warm at 140 DEG C of insulation reaction 2h in controlling; Then be cooled to 65 DEG C, be evacuated to vacuum tightness 130Pa, keep 1h except ammonia, afterwards again with N
2after sweeping de-30min, cooling sealing is preserved.Obtain colourless high viscosity oily matter, nuclear-magnetism detects purity 97%, and transformation efficiency is 97.5%.White waxy solid product is become after temperature cooling.
Embodiment 3:
Added by 2.00mol urea in the there-necked flask of band prolong that 1000ml does, thermometer, then adding 2.05mol aminopropyl triethoxysilane, is then use N under the condition of 1.5mL/min at flow velocity
2at the following bubbling of liquid level, and warm at 138 DEG C of insulation reaction 4h in controlling; Then be cooled to 65 DEG C, be evacuated to vacuum tightness 95Pa, keep 1h except ammonia, afterwards again with N
2after sweeping de-30min, cooling sealing is preserved.Obtain colourless high viscosity oily matter, nuclear-magnetism detects purity 97%, and transformation efficiency is 97.2%.White waxy solid product is become after temperature cooling.
Embodiment 4:
Added by 5.03mol urea in the there-necked flask of band prolong that 2500ml does, thermometer, then adding 5.10mol aminopropyl triethoxysilane, is then use N under the condition of 1.5mL/min at flow velocity
2at the following bubbling of liquid level, and warm at 135 DEG C of insulation reaction 2h in controlling; Then be cooled to 65 DEG C, be evacuated to vacuum tightness 60Pa, keep 1h except ammonia, afterwards again with N
2after sweeping de-30min, cooling sealing is preserved.Obtain colourless high viscosity oily matter, nuclear-magnetism detects purity 99%, and transformation efficiency is 99.3%.White waxy solid product is become after temperature cooling.
Embodiment 5:
0.460mol urea is added in the there-necked flask of band prolong that 250ml does, thermometer, then add 0.452molN-(β-aminoethyl)-γ-aminopropyltrimethoxysilane; Then be use N under the condition of 1.5mL/min at flow velocity
2at the following bubbling of liquid level, and warm at 135 DEG C of insulation reaction 2h in controlling; Then be cooled to 65 DEG C, being evacuated to vacuum tightness is 100Pa, keeps 1h except ammonia, afterwards again with N
2after sweeping de-30min, cooling sealing is preserved.Obtain colourless high viscosity oily matter, nuclear-magnetism detects purity 98%, transformation efficiency 98.2%.White waxy solid product is become after temperature cooling.
Embodiment 6:
0.460mol urea is added in the there-necked flask of band prolong that 250ml does, thermometer, then add 0.452molN-(β-aminoethyl)-γ-aminopropyl triethoxysilane; Then be use N under the condition of 1.3mL/min at flow velocity
2at the following bubbling of liquid level, and warm at 137 DEG C of insulation reaction 2h in controlling; Then be cooled to 65 DEG C, being evacuated to vacuum tightness is 100Pa, keeps 1h except ammonia, afterwards again with N
2after sweeping de-30min, cooling sealing is preserved.Obtain colourless high viscosity oily matter, nuclear-magnetism detects purity 98%, and transformation efficiency is 98.1%.White waxy solid product is become after temperature cooling.
Embodiment 7:
0.460mol urea is added in the there-necked flask of band prolong that 250ml does, thermometer, then add 0.452molN-(β-aminoethyl)-γ-aminopropyltriethoxy dimethoxysilane; Then be use N under the condition of 1.5mL/min at flow velocity
2at the following bubbling of liquid level, and warm at 136 DEG C of insulation reaction 2h in controlling; Then be cooled to 70 DEG C, being evacuated to vacuum tightness is 89Pa, keeps 1h except ammonia, afterwards again with N
2after sweeping de-30min, cooling sealing is preserved.Obtain colourless high viscosity oily matter, nuclear-magnetism detects purity 98.5%, and transformation efficiency is 99.1%.White waxy solid product is become after temperature cooling.
Embodiment 8:
0.460mol urea is added in the there-necked flask of band prolong that 250ml does, thermometer, then add 0.452molN-(β-aminoethyl)-γ-aminopropyltriethoxy diethoxy silane; Then be use N under the condition of 1.4mL/min at flow velocity
2at the following bubbling of liquid level, and warm at 136 DEG C of insulation reaction 2h in controlling; Then be cooled to 72 DEG C, being evacuated to vacuum tightness is 94Pa, keeps 1h except ammonia, afterwards again with N
2after sweeping de-30min, cooling sealing is preserved.Obtain colourless high viscosity oily matter, nuclear-magnetism detects purity 97.2%, and transformation efficiency is 98.1%.White waxy solid product is become after temperature cooling.
Embodiment 9:
0.460mol urea is added in the there-necked flask of band prolong that 250ml does, thermometer, then add 0.452mol aminopropyl trimethoxysilane; Then add solvent dehydrated alcohol by 20% of aminopropyl trimethoxysilane quality, dissolve mixing; Then, be under the condition of 1.3mL/min, use N2 at the following bubbling of liquid level at flow velocity, and warm at 130 DEG C of insulation reaction 8h in controlling; At 85 DEG C, remove ethanol, be then cooled to 65 degree, be evacuated to vacuum tightness 140Pa, keep 1h except ammonia, after sweeping de-30min with N2 more afterwards, cooling sealing is preserved.Obtain colourless high viscosity oily matter, nuclear-magnetism detects purity 90%, and transformation efficiency is 90.8%.White waxy solid product is become after temperature cooling.
The present embodiment only adds solvent, and the product purity of acquisition does not have embodiment 1 to embodiment 5, and not add the product purity of solvent high.
Only need to control suitable temperature of reaction and suitable nitrogen gas stream flow velocity, just can ensure that the product purity obtained is in certain scope.Therefore, the present invention simple, easy to operate, be suitable for suitability for industrialized production.
Comparative examples 1:
0.466mol urea is added in the there-necked flask of band prolong that 250ml does, thermometer, then add 0.452mol aminopropyl triethoxysilane; Then solvent dimethyl sulfoxide (DMSO) is added by 100% of aminopropyl triethoxysilane quality; Then catalyzer zinc powder is added by 2.0% of aminopropyl triethoxysilane quality; Be use N under the condition of 1.0mL/min at flow velocity
2at the following bubbling of liquid level, and temperature insulation reaction 2h under 135 DEG C of conditions in controlling; Then be cooled to 65 DEG C, being evacuated to vacuum tightness is 90Pa, keeps 1h except ammonia, afterwards again with N
2after sweeping de-30min, cooling sealing is preserved.Utilizing nitrogen sweep de-is in order to air isolated in temperature-fall period, is convenient to the preservation in later stage.Obtain water white transparency high viscosity oily matter, nuclear-magnetism testing product purity is 90%, and transformation efficiency is 91.5%.White waxy solid product is become after temperature cooling.
But the product that the present embodiment obtains has more dissolvent residual, because product viscosity removes more greatly and not easily.
Comparative examples 2:
0.460mol urea is added in the there-necked flask of band prolong that 250ml does, thermometer, then add 0.452mol aminopropyl triethoxysilane; Be use N under the condition of 1.0mL/min at flow velocity
2at the following bubbling of liquid level; Then dimethylbenzene/the alcohol mixed solvent of volume ratio 6:4 is added by 100% of aminopropyl triethoxysilane quality; Then catalyzer Zinc Chloride Anhydrous is added by 1.0% of aminopropyl triethoxysilane quality; Then temperature insulation reaction 4h under 125 DEG C of conditions in controlling; Filtered while hot removing catalyzer; Then be cooled to 65 DEG C, being evacuated to vacuum tightness is 90Pa, removes solvent and ammonia, afterwards again with N
2after sweeping de-30min, cooling sealing is preserved.Obtain water white transparency high viscosity oily matter, nuclear-magnetism testing product purity is 60%, and transformation efficiency is 61.7%.White waxy solid product is become after temperature cooling.
Comparative examples 3:
0.460mol urea is added in the there-necked flask of band prolong that 250ml does, thermometer, then add 0.452mol aminopropyl triethoxysilane; Then solvent dry toluene is added by 80% of aminopropyl triethoxysilane quality; Then catalyzer magnesium chloride is added by 33.0% of amino silicane coupling agent quality; Be use N under the condition of 1.0mL/min at flow velocity
2at the following bubbling of liquid level, and temperature insulation reaction 4h under 135 DEG C of conditions in controlling; Filtered while hot removing catalyzer, be then cooled to 65 DEG C, being evacuated to vacuum tightness is 150Pa, removes solvent and ammonia, afterwards again with N
2after sweeping de-30min, cooling sealing is preserved.Generate through nuclear-magnetism testing product product-free.
Comparative examples 4:
0.460mol urea is added in the there-necked flask of band prolong that 250ml does, thermometer, then add 0.452mol aminopropyl triethoxysilane; Then solvent dry toluene is added by 75% of aminopropyl triethoxysilane quality; Then catalyzer Zinc Chloride Anhydrous is added by 3.5% of aminopropyl triethoxysilane quality; Be use N under the condition of 1.2mL/min at flow velocity
2at the following bubbling of liquid level; Then temperature insulation reaction 4h under 100 DEG C of conditions in controlling; Filtered while hot removing catalyzer, be then cooled to 65 DEG C, being evacuated to vacuum tightness is 95Pa, removes solvent and ammonia, afterwards again with N
2after sweeping de-30min, cooling sealing is preserved.Obtain colourless high viscosity oily matter.Nuclear-magnetism testing product purity is 80%, and transformation efficiency is about 81.3%.
Therefore, the present invention when not adding catalyzer, by controlling certain temperature of reaction and nitrogen gas stream flow velocity directly prepares highly purified ureido silane coupling agent.Preparation method's cost of the present invention is low, product purity is high, technique is simple, mild condition and easy to operate, is suitable for suitability for industrialized production.
Although with reference to explanatory embodiment of the present invention, invention has been described here, above-described embodiment is only the present invention's preferably embodiment, embodiments of the present invention are not restricted to the described embodiments, should be appreciated that, those skilled in the art can design a lot of other amendment and embodiment, these amendments and embodiment will drop within spirit disclosed in the present application and spirit.
Claims (8)
1. a preparation method for ureido silane coupling agent, is characterized in that the method comprises the following steps:
A, mixing
Ratio 0.8 ~ the 1.5:1 pre-dry urea and amino silicane coupling agent being pressed amount of substance mixes, and is then dissolved in solvent by the mass ratio 0 ~ 200:100 of solvent and amino silicane coupling agent, obtains a kind of mixture;
B, nucleophilic substitution reaction
The mixture of steps A being heated to temperature is 100 ~ 150 DEG C, reaction 1 ~ 8h; Use nitrogen at the following bubbling of liquid level, and to control nitrogen gas stream flow velocity be 0.5 ~ 1.9mL/min simultaneously; Obtain a kind of reactant;
C, aftertreatment
The reactant of cooling step B, then low-boiling-point substance is removed in decompression.
2. preparation method according to claim 1, it is characterized in that in step, described amino silicane coupling agent is selected from aminopropyl trimethoxysilane, aminopropyl triethoxysilane, N-(β-aminoethyl)-γ-aminopropyltrimethoxysilane, N-(β-aminoethyl)-γ-aminopropyl triethoxysilane, N-(β-aminoethyl)-γ-aminopropyltriethoxy dimethoxysilane or N-(β-aminoethyl)-γ-aminopropyltriethoxy diethoxy silane.
3. preparation method according to claim 1, it is characterized in that in step, described solvent is that one or more are selected from the solvent of methyl alcohol, ethanol, tetrahydrofuran (THF), tetracol phenixin, benzene, dimethylbenzene, DMF, methyl-sulphoxide or N-Methyl pyrrolidone.
4. preparation method according to claim 1, is characterized in that in step, and described solvent and the mass ratio of amino silicane coupling agent are 0:100.
5. preparation method according to claim 1, is characterized in that in stepb, and it is 120 ~ 140 DEG C that mixture is heated to temperature, reaction 2 ~ 6h.
6. preparation method according to claim 1, is characterized in that in stepb, and described nitrogen gas stream flow velocity is 0.8 ~ 1.5mL/min.
7. preparation method according to claim 1, is characterized in that in step C, and described cooling cools the temperature to 50 ~ 100 DEG C.
8. preparation method according to claim 1, is characterized in that in step C, and described decompression is that to be evacuated to vacuum tightness be 50 ~ 150Pa.
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| CN105111231A (en) * | 2015-09-09 | 2015-12-02 | 成都硅宝科技股份有限公司 | Alpha-silane coupling agent and application thereof |
| CN105541897A (en) * | 2016-03-14 | 2016-05-04 | 荆州市江汉精细化工有限公司 | Preparation method of 3-isocyanatopropyltrimethoxysilane |
| JP2020045304A (en) * | 2018-09-18 | 2020-03-26 | 信越化学工業株式会社 | Method for producing ureido group-containing organosilicon compound |
| CN112920783A (en) * | 2019-12-05 | 2021-06-08 | 中国石油化工股份有限公司 | Wetting reversal inhibitor for drilling fluid and preparation method thereof |
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