CN101838393B - Method for synthesizing high-molecular-weight ethyl polysiloxane - Google Patents
Method for synthesizing high-molecular-weight ethyl polysiloxane Download PDFInfo
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Abstract
The invention discloses a method for synthesizing high-molecular-weight ethyl polysiloxane. The method comprises the following steps: adding reaction monomers, catalysts, promoter and modifier by a certain ratio to a reaction bottle; increasing the temperature to 70 to 150 DEG C at the reduced pressure or constant pressure, and reacting for 4h to 8h; and removing low-boiling-point substances by heating under the vacuum condition, to obtain ethyl polysiloxane. The method of the invention has the advantages of simple reaction conditions and solvent-free reaction; the monomers, catalysts and promoter are added to the reactor at one time in the reaction, so that the reaction can be conducted at a lower temperature within shorter reaction time to obtain the high-molecular-weight ethyl polysiloxane; and the method of the invention further has the advantages of high yield, controllable molecular weight and simple post-treatment.
Description
Technical field
The present invention relates to a kind of compound method of ZGK 5, particularly relate to a kind of compound method of high-molecular-weight ethyl polysiloxane.
Background technology
ZGK 5 is to be main chain with Si-O-Si; The high molecular synthetic material that directly connects organic groups such as methyl, ethyl, vinyl, phenyl on the Siliciumatom, it has good dielectricity and highly air-permeable, surfactivity, biocompatibility, hydrophobic nature, thermotolerance, winter hardiness and excellent physical chemistry such as ageing-resistant.The various organosilicon products that on the ZGK 5 basis, prepare have all obtained using widely in fields such as aerospace, national defence, chemical industry, machinery, metallurgy, electric, weaving, building, traffic, the energy, medical medicine, agriculturals.
Along with the continuous development of science and technology, human increasingly high to the rubber item performance demands, particularly performance is particularly outstanding in the aerospace flight technology exploitation, as under very low temperature, keeping elasticity and sealing property, high-low temperature resistant circulation impact, vacuum-resistant particle and UV-light etc.Under exacting terms like this, general rubber does not have use value, and has only special silicone rubber just can meet the demands.The winter hardiness of Zylox is relevant with its second-order transition temperature and low temperature crystallization property.Ethyl polysiloxane is the ZGK 5 with minimum second-order transition temperature (Tg) known today; Organosilicon product by the ethyl polysiloxane preparation can keep mechanical property preferably at low temperatures, but long term operation in low temperature environments such as air, rare gas element and vacuum.
At present the universal method of synthetic ZGK 5 is to be monomeric ring-opening polymerization with cyclosiloxane.Molenberg and Moller report are made catalyzer and 1-ethyl-2,2,4,4 with butyllithium (BuLi), 4-five (dimethylin)-2 λ in toluene solvant
5, 4 λ
5-two phosphonitrile (P
2-Et) doing promotor causes Hexaethyl cyclotrisiloxane (D
3 Et) ring-opening polymerization, obtaining molecular weight Mn behind the normal-temperature reaction 72-171h is 15.8 * 10
3-69.6 * 10
3Ethyl polysiloxane, the product productive rate is 27%-59%.Tsuchihara and Fujishige report are made catalyzer and N with BuLi, dinethylformamide (DMF), (nBuO)
3PO, hexamethylphosphoramide (HMPA) or DMSO 99.8MIN. (DMSO) are done promotor and are caused D
3 EtRing-opening polymerization, obtaining molecular weight Mn behind the normal-temperature reaction 24h is 12 * 10
3-16 * 10
3Ethyl polysiloxane.People such as Z.Xie report with TMAH catalysis D
3 Et, obtaining molecular weight Mn behind 110 ℃ of following reaction 12h is 29 * 10
3Ethyl polysiloxane.
More than many methods all have problems such as gained ethyl polysiloxane molecular weight is lower, productive rate is not high.Therefore improve experiment condition and technology, preparation high-molecular weight ethyl polysiloxane, and improve productive rate, not only have the excellent research meaning, and have important and practical meanings.
Summary of the invention
In order to solve the weak point that exists in the existing ethyl polysiloxane synthetic technology, the object of the present invention is to provide a kind of compound method of high-molecular-weight ethyl polysiloxane, to satisfy industrial production and the demand of using many aspects.
The technical scheme that the present invention takes is:
A kind of compound method of high-molecular-weight ethyl polysiloxane comprises the steps:
In reaction flask, add reaction monomers, catalyzer, promotor and properties-correcting agent by a certain percentage, the decompression or condition of normal pressure under be warming up to 70～150 ℃ the reaction 4～8h, under vacuum condition, be heated to again 180～200 ℃ deviate from low-boiling-point substance both ethyl polysiloxane.
The weight part ratio of described each raw material of above-mentioned steps is: 100 parts of reaction monomers, 0.0001～0.05 part of catalyzer, 0.1～10 part of promotor, 0～100 part of properties-correcting agent.
Described reaction monomers is Hexaethyl cyclotrisiloxane (D
3 Et), octaethyl cyclotetrasiloxane (D
4 Et), di-ethyl siloxane mixed methylcyclosiloxane, diethyl dichlorosilane hydrolyzate or terminal hydroxy group gather di-ethyl siloxane.
Described catalyzer is Pottasium Hydroxide (KOH), sodium hydroxide (NaOH), cesium hydroxide (CsOH), Lithium Hydroxide MonoHydrate (LiOH), butyllithium (BuLi), TMAH ((CH
3)
4NOH) or phosphazene base, the perhaps silicon alkoxide of aforementioned these materials.
Described promotor is DMSO 99.8MIN. (DMSO), N, dinethylformamide (DMF), hexamethylphosphoramide (HMPA), THF (THF), ketone, acetonitrile, crown ether, cave ether, polyethers or oil of mirbane.
Described properties-correcting agent is vinyl ring body, ethers, pyridine or pyrrolidone.
The reduced pressure of described reaction is 8～70KPa, and condition of normal pressure is that standard atmosphere is depressed.
The present invention compared with prior art has following advantage and beneficial effect: reaction conditions of the present invention is simple, need not solvent; Join in the reactor drum monomer, catalyzer and promotor are disposable during reaction; Just can react at a lower temperature, can obtain high-molecular-weight ethyl polysiloxane in the time, and productive rate is high at shorter reaction; Molecular weight is controlled, and aftertreatment is simple.
Description of drawings
Fig. 1 (a) and (b) make the GPC spectrogram of product for the present invention;
Fig. 2 makes the nuclear magnetic resonance map of product for the present invention.
Embodiment
Embodiment 1
Is being furnished with N
2Add 100g D in the reaction flask of conduit, TM and still head
3 Et, 0.12g TMAH and 0.2g polyethers, logical N
2Slowly heating is warming up to 70 ℃, keeps 0.5 hour, and catalyzer all dissolves continued and heats up, and reacts 6 hours down at 80 ℃, and reaction finishes, and temperature is risen to about 150 ℃, keeps 0.5 hour.Under vacuum condition, be warming up to about 180 ℃ at last, deviate from low-boiling-point substance and both got ethyl polysiloxane, number-average molecular weight Mn 67.9 * 10
4, weight-average molecular weight Mw 147 * 10
4, productive rate 90%, the GPC spectrogram of molecular weight is seen Fig. 1 (a).
Embodiment 2
Is being furnished with N
2Add 100g D in the reaction flask of conduit, TM and still head
3 Et, 0.2g tetramethyl-tetrem thiazolinyl cyclotetrasiloxane (D
4 Vi), 0.12g TMAH and 2g DMSO 99.8MIN. (DMSO), logical N
2Slowly heating is warming up to 70 ℃, keeps 0.5 hour, after the whole dissolvings of catalyzer, continues to heat up, and reacts 8 hours down at 90 ℃, and reaction finishes, and temperature is risen to about 150 ℃, keeps 0.5 hour.Under vacuum condition, be warming up to about 180 ℃ at last, deviate from low-boiling-point substance and obtain ethyl polysiloxane, number-average molecular weight Mn 35.4 * 10
4, weight-average molecular weight Mw 67.3 * 10
4, productive rate 69%.
Embodiment 3
Is being furnished with N
2Add 100gD in the reaction flask of conduit, TM and still head
3 Et, 0.2g D
4 Vi, 0.12g TMAH and 1gN, dinethylformamide (DMF), logical N
2Slowly heating is warming up to 70 ℃, keeps 0.5 hour, after the whole dissolvings of catalyzer, continues to heat up, and reacts 8 hours down at 110 ℃, and reaction finishes, and temperature is risen to about 150 ℃, keeps 0.5 hour.Under vacuum condition, be warming up to about 180 ℃ at last, deviate from low-boiling-point substance and obtain ethyl polysiloxane, number-average molecular weight Mn40.5 * 10
4, weight-average molecular weight Mw 87.1 * 10
4, productive rate 72%.
Embodiment 4
Is being furnished with N
2Add 100g D in the reaction flask of conduit, TM and still head
3 Et, 0.2g D
4 Vi, 0.12g TMAH and 1g crown ether, logical N
2Slowly heating is warming up to 70 ℃, keeps 0.5 hour, after the whole dissolvings of catalyzer, continues to heat up, and reacts 6 hours down at 110 ℃, and reaction finishes, and temperature is risen to about 150 ℃, keeps 0.5 hour.Under vacuum condition, be warming up to about 180 ℃ at last, deviate from low-boiling-point substance and obtain ethyl polysiloxane, number-average molecular weight Mn 36.3 * 10
4, weight-average molecular weight Mw 75.4 * 10
4, productive rate 70%.
Embodiment 5
Is being furnished with N
2Add 100g D in the reaction flask of conduit, TM and still head
3 Et, 0.2g D
4 Vi, 0.1g TMAH and 0.2g crown ether, logical N
2Slowly heating is warming up to 70 ℃, keeps 0.5 hour, after the whole dissolvings of catalyzer, continues to heat up, and reacts 8 hours down at 80 ℃, and reaction finishes, and temperature is risen to about 150 ℃, keeps 0.5 hour.Under vacuum condition, be warming up to about 180 ℃ at last, deviate from low-boiling-point substance and obtain ethyl polysiloxane, number-average molecular weight Mn 64.7 * 10
4, weight-average molecular weight Mw 112 * 10
4, productive rate 72%.
Embodiment 6
Is being furnished with N
2Add 100g D in the reaction flask of conduit, TM and still head
3 Et, 0.2g D
4 Vi, 0.2g TMAH and 0.2g crown ether, logical N
2Slowly heating is warming up to 70 ℃, keeps 0.5 hour, after the whole dissolvings of catalyzer, continues to heat up, and reacts 8 hours down at 110 ℃, and reaction finishes, and temperature is risen to about 150 ℃, keeps 0.5 hour.Under vacuum condition, be warming up to about 180 ℃ at last, deviate from low-boiling-point substance and obtain ethyl polysiloxane, number-average molecular weight Mn 48.6 * 10
4, weight-average molecular weight Mw 92.2 * 10
4, productive rate 77%.
Embodiment 7
Is being furnished with N
2Add 100g D in the reaction flask of conduit, TM and still head
3 Et, 0.2g D
4 Vi, 0.3g TMAH and 0.2g crown ether, logical N
2Slowly heating is warming up to 70 ℃, keeps 0.5 hour, after the whole dissolvings of catalyzer, continues to heat up, and reacts 8 hours down at 100 ℃, and reaction finishes, and temperature is risen to about 150 ℃, keeps 0.5 hour.Under vacuum condition, be warming up to about 180 ℃ at last, deviate from low-boiling-point substance and obtain ethyl polysiloxane, number-average molecular weight Mn 33.7 * 10
4, weight-average molecular weight Mw81.9 * 10
4, productive rate 83%.
Embodiment 8
Is being furnished with N
2Add 100g D in the reaction flask of conduit, TM and still head
3 Et, 0.2g D
4 Vi, 0.12g TMAH and 0.3g polyethers, logical N
2Slowly heating is warming up to 70 ℃, keeps 0.5 hour, after the whole dissolvings of catalyzer, continues to heat up, and reacts 6 hours down at 110 ℃, and reaction finishes, and temperature is risen to about 150 ℃, keeps 0.5 hour.Under vacuum condition, be warming up to about 180 ℃ at last, deviate from low-boiling-point substance and obtain ethyl polysiloxane, number-average molecular weight Mn 45.3 * 10
4, weight-average molecular weight Mw 89.7 * 10
4, productive rate 78%.
Embodiment 9
Is being furnished with N
2Add 100g D in the reaction flask of conduit, TM and still head
3 Et, 0.2g D
4 Vi, 1g TMAH alkali glue and 0.8g polyethers, logical N
2Slowly heating is warming up to 70 ℃, keeps 0.5 hour, after the whole dissolvings of catalyzer, continues to heat up, and reacts 7 hours down at 110 ℃, and reaction finishes, and temperature is risen to about 150 ℃, keeps 0.5 hour.Under vacuum condition, be warming up to about 180 ℃ at last, deviate from low-boiling-point substance and obtain ethyl polysiloxane, number-average molecular weight Mn 42.9 * 10
4, weight-average molecular weight Mw83.7 * 10
4, productive rate 87%.
Embodiment 10
In the reaction flask of being furnished with TM and still head, add 100g D
3 Et, 0.2g D
4 ViWith 0.1g Pottasium Hydroxide (KOH), be warming up to 70 ℃, to keep 0.5 hour, after catalyzer all dissolved, heat temperature raising to 150 ℃ reaction 5h added an amount of neutralizing agent (like CO under decompression reaction conditions (35KPa)
2, silica-based SULPHOSUCCINIC ACID ESTER, hexamethyldisilazane etc.) neutralization, under vacuum condition, be warming up at last about 180 ℃, deviate from low-boiling-point substance to obtain ethyl polysiloxane product number-average molecular weight Mn 112 * 10
4, weight-average molecular weight Mw 195 * 10
4, productive rate＞80%, the GPC spectrogram of molecular weight is seen Fig. 1 (b), the product nuclear magnetic spectrum is seen Fig. 2.
Embodiment 11
Is being furnished with N
2Add 100gD in the reaction flask of conduit, TM and still head
3 Et, 0.2g D
4 Vi, 0.1gKOH and 0.5g crown ether, logical N
2Slowly heating is warming up to 70 ℃, keeps 0.5 hour; After catalyzer all dissolves, continue to heat up, reaction is 7 hours under 150 ℃; After finishing, reaction adds an amount of neutralizing agent neutralization; Under vacuum condition, be warming up to about 180 ℃ at last, deviate from low-boiling-point substance and obtain ethyl polysiloxane, number-average molecular weight Mn 98.5 * 10
4, weight-average molecular weight Mw164 * 10
4, productive rate＞80%.
Embodiment 12
In the reaction flask of being furnished with TM and still head, add 100g D
3 Et, 0.2g D
4 ViWith 1g potassium hydroxide base glue, be warming up to 70 ℃, kept 0.5 hour; After catalyzer all dissolves; Heat temperature raising to 150 ℃ reaction 5h adds an amount of neutralizing agent neutralization, under vacuum condition, is warming up to about 180 ℃ at last; Deviate from low-boiling-point substance and obtain ethyl polysiloxane, product number-average molecular weight Mn 56.2 * 10
4, weight-average molecular weight Mw 94 * 10
4, productive rate 81%.
Embodiment 13
In the reaction flask of being furnished with TM and still head, add 100g D
3 Et, 0.2g D
4 ViWith 0.1g cesium hydroxide (CsOH), be warming up to 70 ℃, kept 0.5 hour; After catalyzer all dissolves; Heat temperature raising to 150 ℃ reaction 4h adds an amount of neutralizing agent neutralization under the decompression reaction conditions, under vacuum condition, is warming up to about 180 ℃ at last; Deviate from low-boiling-point substance and obtain ethyl polysiloxane, product number-average molecular weight Mn 102 * 10
4, weight-average molecular weight Mw 176 * 10
4, productive rate＞80%.
Embodiment 14
In the reaction flask of being furnished with TM and still head, add 100g D
3 Et, 0.2g D
4 ViWith 1.2g cesium hydroxide alkali glue, be warming up to 70 ℃, kept 0.5 hour; After catalyzer all dissolves; Heat temperature raising to 150 ℃ reaction 4h adds an amount of neutralizing agent neutralization under the decompression reaction conditions, under vacuum condition, is warming up to about 180 ℃ at last; Deviate from low-boiling-point substance and obtain ethyl polysiloxane, product number-average molecular weight Mn 86.3 * 10
4, weight-average molecular weight Mw 123 * 10
4, productive rate＞80%.
Embodiment 15
Is being furnished with N
2Add 100g D in the reaction flask of conduit, TM and still head
3 Et, 0.2gD
4 Vi, 0.12gCsOH and 0.5g crown ether, logical N
2Slowly heating is warming up to 70 ℃, keeps 0.5 hour; After catalyzer all dissolves, continue to heat up, reaction is 4 hours under 110 ℃; After finishing, reaction adds an amount of neutralizing agent neutralization; Under reduced pressure, be warming up to about 180 ℃ at last, deviate from low-boiling-point substance and obtain ethyl polysiloxane, number-average molecular weight Mn 98.5 * 10
4, weight-average molecular weight Mw 164 * 10
4, productive rate＞80%.
Claims (4)
1. the compound method of a high-molecular-weight ethyl polysiloxane is characterized in that, comprises the steps:
In reaction flask, add reaction monomers, catalyzer, promotor and properties-correcting agent vinyl ring body by a certain percentage; Under decompression or condition of normal pressure, be warming up to 70～150 ℃ of reaction 4～8h, under vacuum condition, be heated to 180～200 ℃ again and deviate from low-boiling-point substance and promptly get ethyl polysiloxane; The weight part ratio of described each raw material is: 100 parts of reaction monomers, 0.0001～0.05 part of catalyzer, 0.1～10 part of promotor, 0～100 part of properties-correcting agent; Described reaction monomers is that Hexaethyl cyclotrisiloxane, octaethyl cyclotetrasiloxane, di-ethyl siloxane mixed methylcyclosiloxane, diethyl dichlorosilane hydrolyzate or terminal hydroxy group gather di-ethyl siloxane.
2. according to the compound method of the described high-molecular-weight ethyl polysiloxane of claim 1; It is characterized in that; Described catalyzer is Pottasium Hydroxide, sodium hydroxide, cesium hydroxide, Lithium Hydroxide MonoHydrate, butyllithium, TMAH or phosphazene base, perhaps the silicon alkoxide of these materials.
3. according to the compound method of the described high-molecular-weight ethyl polysiloxane of claim 1; It is characterized in that; Described promotor is DMSO 99.8MIN., N, dinethylformamide, hexamethylphosphoramide, THF, ketone, acetonitrile, crown ether, cave ether, polyethers or oil of mirbane.
4. according to the compound method of the described high-molecular-weight ethyl polysiloxane of claim 1, it is characterized in that the reduced pressure of described reaction is 8～70KPa.
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| CN102206347A (en) * | 2011-05-04 | 2011-10-05 | 石振东 | Method for synthesizing hydroxyl polysiloxane |
| CN102491993B (en) * | 2011-11-24 | 2014-03-12 | 山东大学 | Preparation method of lithium trimethylsilanolate |
| CN102532548B (en) * | 2012-01-12 | 2013-06-19 | 山东大学 | Low-temperature-resisting crude silicon rubber |
| CN105694043B (en) * | 2016-03-11 | 2019-01-29 | 山东大学 | A kind of preparation method of poly- (Methylethyl-methyl ethylene) siloxanes of high molecular weight |
| CN106905530A (en) * | 2017-03-16 | 2017-06-30 | 江苏科幸新材料股份有限公司 | A kind of preparation method of alkoxy end-capped polysiloxanes |
| CN110484083B (en) * | 2019-07-06 | 2021-06-15 | 广东美佳康新材料有限公司 | Double-component tile joint mixture |
| CN111072716B (en) * | 2020-01-06 | 2022-08-30 | 江西蓝星星火有机硅有限公司 | Preparation method of tetramethyl tetravinylcyclotetrasiloxane |
| CN111995754A (en) * | 2020-09-02 | 2020-11-27 | 江西星火狮达科技有限公司 | Diethyl silicone oil and production method thereof |
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Application publication date: 20100922 Assignee: Yishui County Hengchang seals Ltd. Assignor: Shandong University Contract record no.: 2013370000071 Denomination of invention: Method for synthesizing high-molecular-weight ethyl polysiloxane Granted publication date: 20120404 License type: Exclusive License Record date: 20130407 |
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