CN115216011A - Iso-alkoxy silicone oil and preparation method and application thereof - Google Patents
Iso-alkoxy silicone oil and preparation method and application thereof Download PDFInfo
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Abstract
The invention belongs to the field of organic silicon, and particularly relates to different-end alkoxy silicone oil, wherein one end of the different-end alkoxy silicone oil is CH 3 O-, and the other end is-SiMe 2 R 1 The middle repeating unit is-SiMeR-O-, wherein R is-CH 3 、‑C 6 H 5 or-CH 2 CH 2 CF 3 ；R 1 is-CH 3 、‑H、‑OCH 3 、‑OCH 2 CH 3 or-CH = CH 2 (ii) a The polymerization degree m is a natural number of 10 to 60. The different-end alkoxy silicone oil can be used for treating the surface of the filler, improving the compatibility between the filler and an organic material or an organosilicon material and improving the performance of a sealant productMechanical properties. The invention also provides a preparation method of the isochoric alkoxy silicone oil, and the method has simple process and easily controlled reaction process.
Description
Technical Field
The invention belongs to the field of organic silicon, and particularly relates to an isochoric alkoxy silicone oil, and a preparation method and application thereof.
Background
With the advent of the 5G era, the integration of electronic components has increased, the amount of heat generated has increased dramatically, and the required heat dissipation power has increased, thus requiring materials with higher thermal conductivity. The thermal conductivity of the material is related to the thermal conductivity of the used filler and the filling amount of the selected heat-conducting filler, and the more the heat-conducting filler is, the higher the thermal conductivity of the material is, but the material has increased viscosity, so that the processability is poor, and the construction is affected. Meanwhile, the physical and chemical properties of the organic material or the organosilicon material and the surface of the filler are usually different greatly, the compatibility of the heat-conducting filler and the organosilicon is poor, the dispersibility of the heat-conducting filler in the organosilicon is poor, the filler is precipitated, the heat conductivity of the material is poor, the contact failure between the heat-conducting material and a device or a radiating fin increases the heat resistance, and the overall performance including the mechanical performance is reduced.
White carbon black is a commonly used reinforcing filler for silicone rubber, is light in weight, amorphous, small in particle size, large in specific surface area, and generally exists in the form of aggregates. During the preparation process, a large amount of hydroxyl groups are remained in the white carbon black, some of the hydroxyl groups are wrapped in the aggregate, and the others are positioned outside the aggregate. The hydroxyl groups encapsulated inside the aggregate have less influence on the performance of the silicone rubber. The hydroxyl group positioned outside the aggregate has high activity, hydrophilicity, poor wettability with the basic polymer of the silicon rubber, poor dispersibility in the system and great influence on the performance of the silicon rubber. Therefore, the surface treatment of the white carbon black is required to improve the dispersibility in the silicone rubber and enhance the reinforcing effect. The surface treating agent of the white carbon black has various types, such as alcohol, cyclosiloxane, silane coupling agent and the like, and can achieve the purpose of modification through the reaction with hydroxyl on the surface of the white carbon black, wherein Hexamethyldisilazane (HMDZ) is widely used due to relatively low cost and good treatment effect. However, the white carbon black treated by Hexamethyldisilazane (HMDZ) has heavy odor, and the silicone rubber added with the white carbon black can be deodorized after being subjected to high-temperature long-time vacuum treatment.
Therefore, how to prepare the alkoxy oligomeric silicone oil which can be used for improving the compatibility between the organic material or the organosilicon material and the filler has important research significance.
Disclosure of Invention
The invention provides a heteroleptic alkoxy silicone oil end, one end of which is alkoxy and the other end is other groups, the heteroleptic alkoxy silicone oil can be used for treating the surface of a filler, improving the compatibility between the filler and an organic material or an organosilicon material and improving the mechanical property of a sealant product.
The basic concept of the technical scheme adopted by the invention is as follows:
an isochoric alkoxy silicone oil, the structure of which is shown in formula (I):
in the formula, R is-CH 3 、-C 6 H 5 or-CH 2 CH 2 CF 3 ；R 1 is-CH 3 、-H、-OCH 3 、-OCH 2 CH 3 or-CH = CH 2 ；
m is a natural number of 10 to 60.
As an example, the molecular weight distribution of the isochoric alkoxy silicone oil is less than 1.2, and the molecular weight is 1000-8000.
The invention also provides a preparation method of the heteroterminal alkoxy silicone oil, which comprises the following steps:
(1) Taking cyclosiloxane as a raw material, adding organic base as an initiator, and carrying out ring-opening polymerization;
(2) Cooling the product obtained in the step (1), adding methyl chlorosilane for reaction, and then filtering to obtain the different-end alkoxy silicone oil;
the structural formula of the cyclosiloxane is shown as a formula (II), wherein R is-CH 3 、-C 6 H 5 or-CH 2 CH 2 CF 3 N is 3, 4 or 5:
the structure of the methyl chlorosilane is shown as a formula (III), wherein R is-CH 3 、-C 6 H 5 or-CH 2 CH 2 CF 3 ，R 1 is-CH 3 、-H、-OCH 3 、-OCH 2 CH 3 or-CH = CH 2 ：
In one case, the organic base is sodium methoxide, sodium ethoxide, sodium tert-butoxide or potassium methoxide.
As a case, the cyclosiloxane is dehydrated for 0.5 to 1 hour at the temperature of between 60 and 100 ℃ and between-0.08 and-0.1 MPa in advance.
As a case, the cyclic siloxane was added to the reaction flask while using N 2 Replacing air in the reaction bottle, adding organic base at 60-100 ℃, and reacting for 2-6 h under heat preservation.
As a case, the product obtained in the step (1) is cooled to 40-60 ℃, methyl chlorosilane is added, and the mixture is stirred for 1-4 hours at room temperature.
As one example, the molar ratio of cyclosiloxane, organic base and methylchlorosilane is (2-20): 1.
The invention also provides the application of the heteroterminal alkoxy silicone oil, wherein the heteroterminal alkoxy silicone oil is used for preparing a high-thermal-conductivity-coefficient material.
As a case, the application of the different end alkoxy silicone oil is to use the different end alkoxy silicone oil to prepare silicone grease, silicone paste or silicone mud with high thermal conductivity.
Compared with the prior art, the invention has the following beneficial effects:
1. the preparation method of the invention uses cyclosiloxane as a main raw material, adopts organic base as an initiator, and obtains the silicone oil containing alkoxy at the different end through ring-opening polymerization, the molecular weight distribution of the silicone oil is less than 1.2, the molecular weight is adjustable between 2000 and 6000, the molecular weight distribution is narrow, and the silicone oil has the advantages of strong selectivity of active end groups and unified and controllable product structure, and can be used for preparing high-performance organosilicon materials.
2. The preparation method has simple process and easy control of the reaction process, and simultaneously, the vinyl at the other end needs to continuously participate in the crosslinking reaction because of containing a certain active component, so that the mechanical property of the polysiloxane fluid during vulcanization can be improved.
3. The surface property of the filler and the interface property of the filler in polysiloxane fluid can be effectively improved by the alkoxy-containing silicone oil with the different end prepared by the invention, namely, the dispersibility and filling capacity of the filler subjected to surface treatment by the alkoxy-containing silicone oil fluid with the different end in organic silicon polymers can be effectively improved, so that products such as heat-conducting silicone grease, silicon paste and silicon mud with high heat conductivity can be prepared, and the technical requirements of high-power heating devices such as 5G and the like on heat dissipation can be met.
4. The preparation method can select neutralizing agents containing different active end groups to react according to needs to prepare different types of different-end active silicone oil, such as one-end alkoxy one-end vinyl silicone oil, one-end alkoxy one-end hydrogen-containing silicone oil, one-end alkoxy one-end methyl silicone oil and the like, the active end groups have strong selectivity, and the single-end active silicone oil with a uniform and controllable product structure can be prepared.
5. The preparation method of the invention adopts organic bases such as sodium methoxide, sodium ethoxide, sodium tert-butoxide or potassium methoxide and the like as initiators, metal ions as initiating groups, and the other end of the initiating groups retains a reactive group-alkoxy, and finally, the end of the initiating groups is blocked by chlorosilane, if chlorosilane has a reactive group, the initiating groups are double-end reactive silicone oil, and if chlorosilane has no reactive group, the initiating groups are single-end reactive silicone oil.
One end of the alkoxy silicone oil prepared by the method is alkoxy, the other end of the alkoxy silicone oil is other groups (namely, the heteroterminal alkoxy silicone oil), and the other groups at the other end can be active groups or inert groups, so that the structure of the product can be flexibly adjusted.
Wherein, the vinyl and alkoxy-containing silicone oil with the different end alkoxy can improve the dispersibility and the vulcanization performance.
Drawings
The accompanying drawings are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and together with the example serve to explain the principles of the invention.
FIG. 1 is a nuclear magnetic diagram of an isochoric alkoxy silicone oil according to example 1 of the present invention.
FIG. 2 is a nuclear magnetic diagram of the silicon oil with the different alkoxy end groups in the embodiment 2 of the invention.
FIG. 3 is a nuclear magnetic diagram of an isochoric alkoxy silicone oil of example 3 of the present invention.
FIG. 4 is a GPC chart of an isochoric alkoxy silicone oil of example 1 of the present invention.
FIG. 5 is a GPC chart of an isochoric alkoxy silicone oil of example 2 of the present invention.
FIG. 6 is a GPC chart of an isochoric alkoxy silicone oil of example 3 of the present invention.
FIG. 7 is a GPC chart of an isochoric alkoxy silicone oil of example 4 of the present invention.
Fig. 8 is an optical microscope photograph of a film according to an effect example of the present invention.
Fig. 9 is an optical microscope photograph of a film of a comparative effect example.
Nuclear magnetic resonance hydrogen spectrum (1H-NMR): the test is carried out by adopting a nuclear magnetic resonance spectrometer, the model number of the nuclear magnetic resonance spectrometer is Bruker400M, and deuterated acetone is used as a solvent.
The peak between chemical shifts (delta) = 0-0.4 is Si-C H 3 Radical peak.
The peak between chemical shifts (delta) = 3-4 is Si-OC H 3 Radical peak.
The peak between chemical shifts (delta) = 5.5-6.5 is Si-C H 3 Radical peak.
The peak between chemical shifts (delta) = 7-8 is Si-C 6 *H 6 Radical peak.
Gel Permeation Chromatography (GPC): the test was carried out by using a Waters1525 gel chromatograph of Watts corporation, USA, and about 0.03g of the sample was weighed, and the volume was adjusted to 10mL by using toluene as a mobile phase, the flow rate was 1.0mL/min, and the column temperature was 30 ℃.
Optical microscopy: the test was performed using a BX53 microscope and the film was placed on a glass slide.
Detailed Description
By taking sodium methoxide as an initiator as an example, the reaction principle of the preparation method is as follows:
wherein n =3, 4 or 5; m = a natural number of 10 to 60, R is-CH 3 、-C 6 H 5 or-CH 2 CH 2 CF 3 。
Specific examples 1-4 are provided below for a detailed description, wherein:
in example 1, n =5,m =30,r is-CH 3 ，R 1 is-OCH 3 。
In example 2, n =4,m =46,r is-CH 3 ，R 1 is-CH = CH 2 。
In example 3, n =3,m =20,R is-C 6 H 6 ，R 1 is-CH 3 。
In example 4, n =3,m =32,R is-CH 2 CH 2 CF 3 ，R 1 is-H.
In the specific embodiment, sodium methoxide, sodium ethoxide, sodium tert-butoxide or potassium methoxide can be selected for use as the organic base.
Example 1
Adding 200g of D5 (decamethylcyclopentasiloxane) into a 500ml four-neck flask provided with a stirring pipe, a thermometer and a reflux condenser, keeping the temperature and dehydrating for 40min at 60 ℃, keeping the temperature and dehydrating for 40min at-0.08 MPa, replacing nitrogen at-0.08 MPa, adding 4.86g of sodium methoxide into a reaction bottle, heating to 90 ℃, keeping the temperature and reacting for 5h at the rotating speed of 500rpm, cooling to 30 ℃, adding 12.88g of methoxydimethylchlorosilane, stirring for 1h at room temperature, and filtering to obtain the silicone oil with the alkoxy group at the different end after the reaction is finished.
The molecular weight of the prepared end alkoxy-containing silicone oil is 2440 and the distribution is 1.03.
Example 2
200g of A3 (diphenyl tetramethylcyclotrisiloxane) is added into a 500ml four-neck flask which is provided with a stirring thermometer and a reflux condenser pipe, the temperature is kept and dehydrated for 1h under 90 ℃, 0.10MPa, nitrogen is replaced under 0.08MPa, 4.11g of potassium methoxide is added into a reaction bottle, the temperature is raised to 100 ℃, the temperature is kept and the reaction is carried out for 6h under 500rpm, the temperature is reduced to 50 ℃, 7.09g of vinyl dimethylchlorosilane is added, the stirring is carried out for 3h at room temperature, and after the reaction is finished, the silicon oil with alkoxy at the different end is obtained by filtering.
The molecular weight of the prepared silicone oil containing alkoxy at the different ends is 3591, and the distribution is 1.08.
Example 3
Adding 200g D3 (hexamethylcyclotrisiloxane) into a 500ml four-neck flask provided with a stirring thermometer and a reflux condenser pipe, preserving heat and dehydrating for 30min at 70 ℃, preserving heat and replacing nitrogen at-0.08 MPa, adding 3.94g sodium methoxide into a reaction bottle, heating to 80 ℃, preserving heat and reacting for 4h at the rotating speed of 500rpm, cooling to 30 ℃, adding 7.93g trimethylchlorosilane, stirring for 2h at room temperature, and filtering to obtain the silicon oil containing alkoxy groups at the different ends after the reaction.
The molecular weight of the prepared end alkoxy-containing silicone oil is 2872 and the distribution is 1.05.
Example 4
Adding 200g of D3F (1, 3, 5-trimethyl-1, 3, 5-tri (3, 3-trifluoropropyl) cyclotrisiloxane) into a 500ml four-neck flask provided with a stirring thermometer and a reflux condenser, preserving heat and dehydrating for 50min at 80 ℃ and-0.09 MPa, displacing nitrogen at 0.08MPa, cooling to 60 ℃, adding 2.72g of sodium ethoxide into a reaction bottle, preserving heat and reacting for 2h at the rotating speed of 500rpm, cooling to 40 ℃, adding 3.79g of dimethylhydrogen chlorosilane, stirring for 2h at room temperature, and filtering to obtain the alkoxy-containing silicone oil with the different ends after the reaction is finished.
The molecular weight of the prepared single-end hydrogen-containing silicone oil is 5167 through testing, and the distribution is 1.12.
Effects of the invention
The application properties of the isochoric alkoxy silicone oil obtained in example 2 of the present invention were examined.
White carbon black reinforcing base rubber: 100 parts of vinyl silicone oil and 20 parts of the different-end alkoxy silicone oil obtained in the embodiment 2 are added into a vacuum kneader and uniformly mixed, the white carbon black is added for 9 parts each time for 5 times, after the white carbon black is added, 10 parts of the different-end alkoxy silicone oil obtained in the embodiment 2 are continuously added, the mixture is kneaded at normal temperature, and then heated to 140-180 ℃ for kneading and vacuum treatment, so that the liquid silicone rubber base rubber is prepared.
Liquid silicone rubber vulcanizate: 100 parts of liquid silicon rubber base rubber, 2 parts of vinyl silicone oil, 3 parts of hydrogen-containing silicone oil, 0.04 part of ethynyl cyclohexanol and 0.1 part of Karstedt catalyst are stirred uniformly, then air bubbles are removed under reduced pressure and vacuum, the rubber material is injected into a metal mold with the thickness of 120mm multiplied by 2mm, and the rubber material is heated for 400 seconds under the mold pressing condition and vulcanized at the temperature of 150 ℃ to prepare a test piece.
Comparative Effect example
The tetramethyl divinyl disilazane is used as a comparative example, and the effects of other materials which are not the different-end alkoxy silicone oil of the invention under the same or similar application working conditions are examined.
White carbon black reinforcing base rubber: 100 parts of vinyl silicone oil, 17 parts of tetramethyl divinyl disilazane and 3 parts of pure water are added into a vacuum kneading machine and uniformly mixed, 9 parts of white carbon black are added for 5 times, after the white carbon black is added, 8 parts of tetramethyl divinyl disilazane and 1.5 parts of pure water are continuously added, kneading is carried out under the condition of normal temperature, heating is carried out until the temperature is raised to 140-180 ℃, kneading is carried out, and vacuum treatment is carried out, so that the liquid silicone rubber base adhesive is prepared.
Liquid silicone rubber vulcanizate: 100 parts of liquid silicon rubber base rubber, 2 parts of vinyl silicone oil, 3 parts of hydrogen-containing silicone oil, 0.04 part of ethynyl cyclohexanol and 0.1 part of Karstedt catalyst are stirred uniformly, then air bubbles are removed under reduced pressure and vacuum, the rubber material is injected into a metal mold with the thickness of 120mm multiplied by 2mm, and the rubber material is heated for 400 seconds under the mold pressing condition and vulcanized at the temperature of 150 ℃ to prepare a test piece.
The test data of the above-described effect examples and comparative examples are shown in table 1 below.
TABLE 1
| Test items | Effect test | Comparative effect test |
| Shore A hardness/degree | 56 | 57 |
| Rebound resilience/%) | 76 | 73 |
| Tensile strength/MPa | 8.7 | 7.6 |
| Elongation at break/% | 405 | 390 |
| Tear Strength/kN. M-1 | 19.98 | 38.52 |
Claims (10)
1. The different-end alkoxy silicone oil is characterized in that the structure of the different-end alkoxy silicone oil is shown as the formula (I):
in the formula, R is-CH 3 、-C 6 H 5 or-CH 2 CH 2 CF 3 ；R 1 is-CH 3 、-H、-OCH 3 、-OCH 2 CH 3 or-CH = CH 2 ；
m is a natural number of 10 to 60.
2. The iso-alkoxy silicone oil according to claim 1, wherein the molecular weight distribution of the iso-alkoxy silicone oil is less than 1.2, and the molecular weight is 1000 to 8000.
3. The method for preparing an isochoric alkoxy silicone oil according to claim 1 or 2, wherein the method comprises the steps of:
(1) Taking cyclosiloxane as a raw material, adding organic base as an initiator, and carrying out ring-opening polymerization;
(2) Cooling the product obtained in the step (1), adding methyl chlorosilane for reaction, and then filtering to obtain the different-end alkoxy silicone oil;
the structural formula of the cyclosiloxane is shown as a formula (II), wherein R is-CH 3 、-C 6 H 5 or-CH 2 CH 2 CF 3 N is 3, 4 or 5:
the structure of the methyl chlorosilane is shown as a formula (III), wherein R is-CH 3 、-C 6 H 5 or-CH 2 CH 2 CF 3 ，R 1 is-CH 3 、-H、-OCH 3 、-OCH 2 CH 3 or-CH = CH 2 ：
4. The method for preparing an isochoric alkoxy silicone oil according to claim 3, wherein the organic base is sodium methoxide, sodium ethoxide, sodium tert-butoxide or potassium methoxide.
5. The method for preparing the silicon oil with the different terminal alkoxy groups according to claim 3, wherein the cyclosiloxane is dehydrated for 0.5 to 1 hour under the conditions of 60 to 100 ℃ and-0.08 to-0.1 MPa in advance.
6. The method for preparing an isoalkoxy silicone oil according to claim 3, wherein the cyclic siloxane is added to the reaction flask while N is used 2 Replacing air in the reaction bottle, adding organic base at 60-100 ℃, and reacting for 2-6 h under heat preservation.
7. The preparation method of the iso-alkoxy silicone oil according to claim 3, wherein the product obtained in the step (1) is cooled to 40-60 ℃, methyl chlorosilane is added, and the mixture is stirred at room temperature for 1-4 hours.
8. The method for preparing an isochoric alkoxy silicone oil according to claim 3, wherein the molar ratio of the cyclosiloxane, the organic base and the methylchlorosilane is (2-20): 1.
9. Use of an isocterminally alkoxy silicone oil according to claim 1 or 2, for the preparation of a high thermal conductivity material.
10. Use of the fluid according to claim 9, wherein the fluid is used for preparing silicone grease, paste or putty with high thermal conductivity.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN117946397A (en) * | 2024-01-29 | 2024-04-30 | 广州福泽新材料有限公司 | Preparation method and application of alkenyl-terminated hydroxyl-terminated hydrocarbon-terminated fluorosilicone oil |
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| CN114621443A (en) * | 2021-11-18 | 2022-06-14 | 浙江新安化工集团股份有限公司 | Preparation method of single-end reactive silicone oil |
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| CN1781966A (en) * | 2004-12-02 | 2006-06-07 | 中国科学院化学研究所 | Method for preparing polysiloxane by non-balance polymerizing cyclosiloxane anion |
| CN103987657A (en) * | 2012-03-09 | 2014-08-13 | 住友大阪水泥股份有限公司 | Surface-modified-metal-oxide-particle material, composition for sealing optical semiconductor element, and optical semiconductor device |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN117946397A (en) * | 2024-01-29 | 2024-04-30 | 广州福泽新材料有限公司 | Preparation method and application of alkenyl-terminated hydroxyl-terminated hydrocarbon-terminated fluorosilicone oil |
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