CN112625242A - Preparation method of single-end hydroxyl silicone oil - Google Patents
Preparation method of single-end hydroxyl silicone oil Download PDFInfo
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Abstract
The invention relates to a preparation method of single-end hydroxyl silicone oil, which takes dimethyl siloxane ring and trimethyl chlorosilane as raw materials, and carries out equilibrium reaction under the catalysis of solid super acid, and the obtained reaction product is hydrolyzed. The invention also provides the single-terminal hydroxyl silicone oil prepared by the preparation method. The preparation method provided by the invention avoids the generation of a large amount of hydrochloric acid byproducts generated by monomer hydrolysis in the common preparation method, has uniform and controllable product structure and high activity, can be used for preparing high-performance organosilicon materials, and simultaneously adopts a solid acid catalyst system, has high catalytic efficiency, can be directly filtered and separated after the reaction is finished, is simple to operate, and is environment-friendly and can be recycled for multiple times.
Description
Technical Field
The invention relates to a preparation method of an organic polymer compound, and particularly relates to a preparation method of single-terminal hydroxyl silicone oil.
Background
The hydroxyl silicone oil is an important organosilicon material containing silicon functional groups, namely silicon hydroxyl, is widely used in liquid silicone rubber, organosilicon coating and secondary processing products of silicone oil, and is reactive silicone oil with the largest consumption and the largest market sale. Among the hydroxyl silicone oils at present, the most seen on the market are alpha, omega dihydroxy silicone oil, namely linear dimethyl silicone oil of which two ends are terminated by hydroxyl groups, and hydroxyl silicone oil with special structures, such as branched chain type, single-end hydroxyl type, middle hydroxyl type and other structures, is rare, but the hydroxyl silicone oil with the special structures is an indispensable active intermediate in the synthesis of organic silicon and other high-performance materials, plays an indispensable role, and can endow the materials with excellent performances of high tearing resistance and high shearing on many occasions; a new functional group is introduced at a specific position by a reaction. The hydroxyl silicone oil with special structure has high market value, but is rare in the market at present, and enterprises mostly produce the hydroxyl silicone oil to prepare high-performance products and do not sell the hydroxyl silicone oil for the outside.
Single terminal hydroxyl silicone oil is polydimethylsiloxane with one end being terminated by hydroxyl and the other end being terminated by inert methyl, and only one end having active silicon hydroxyl functional group can generate reaction. The active diluent is used as an active diluent in high-performance liquid silicone rubber for pouring or molding, and has the effects of reducing the viscosity of rubber materials, increasing the flowability or reducing the vulcanization hardness, and simultaneously, silicon hydroxyl at one end of the active diluent can participate in a crosslinking reaction, so that the active diluent can be fixed in sulfides, is non-volatile and anti-migration, and the phenomena of oil leakage, stickiness, dirt adsorption and product performance defect of vulcanized products caused by the use of other diluents such as non-reactive dimethyl silicone oil are avoided.
The liquid silicone rubber is used as the variety with the largest yield in the silicon sealing rubber, and the single-end hydroxyl silicone oil is an ideal high-performance diluent thereof, so that the liquid silicone rubber has great market value.
At present, methods for preparing the hydroxyl-terminated silicone oil are various, but the common methods for preparing the hydroxyl-terminated silicone oil are few, and the most main methods are as follows: the dimethyl dichlorosilane and trimethyl chlorosilane are subjected to cohydrolysis and condensation to prepare monohydroxy terminated dimethyl silicone oil. This method is simple, but has the following drawbacks: a large amount of hydrochloric acid by-product is generated; the unknown amount of dimethyl dichlorosilane reacts to generate cyclosiloxane, so that the utilization rate of the cyclosiloxane is low, and the molecular weight of a target product cannot be effectively controlled; hydrochloric acid promotes silicon hydroxyl condensation, so that partial single-end hydroxyl silicone oil is subjected to dehydration condensation to form unnecessary and difficult-to-remove inactive dimethyl silicone oil, and the service performance of the product is seriously influenced. Other methods such as the method for preparing single-end hydroxyl silicone oil by reacting single-end hydrogen silicone oil with water have overhigh cost and no practical value.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides the preparation method of the single-end hydroxyl silicone oil, which avoids the generation of a large amount of hydrochloric acid by-products in monomer hydrolysis in the common preparation method, has uniform and controllable product structure and high activity, and can be used for preparing high-performance organosilicon materials.
Specifically, the invention provides the following technical scheme:
a preparation method of single-end hydroxyl silicone oil takes dimethyl siloxane ring bodies and trimethyl chlorosilane as raw materials, equilibrium reaction is carried out under the catalysis of solid super acid, and obtained reaction products are hydrolyzed.
Preferably, in the above preparation method, 0.1 to 30 parts by weight of trimethylchlorosilane and 5 to 15 parts by weight of solid superacid are used with respect to 100 parts by weight of dimethylsiloxane ring body. More preferably, 0.27 to 2.65 parts by weight of trimethylchlorosilane and 6.14 to 7.5 parts by weight of solid superacid are used per 100 parts by weight of dimethylsiloxane ring.
Preferably, in the above production method, the hydrolysis treatment is performed using an alkaline solution, and more preferably, an alkaline compound of the alkaline solution is sodium bicarbonate.
Preferably, in the preparation method, the temperature of the equilibrium reaction is 50-70 ℃, and more preferably, the reaction time is 3-4 h.
Preferably, in the above preparation method, the dimethylsiloxane ring body is octamethylcyclotetrasiloxane or a dimethylsiloxane mixed ring body.
Preferably, in the above preparation method, the solid super acid is a sulfate ion acidic metal oxide type solid super acid, preferably HND-32 solid super acid.
Preferably, the preparation method comprises the following steps:
(1) mixing 100 parts by weight of dimethyl siloxane ring bodies, 5-15 parts by weight of solid super acid and 0.1-30 parts by weight of trimethylchlorosilane, reacting for 3-4 hours at 50-70 ℃, and filtering the product to obtain a filtrate;
(2) and (2) adding the filtrate obtained in the step (1) into 50-200 parts by mass of 3-8% sodium bicarbonate aqueous solution, reacting for a certain time, standing, taking supernate, and removing low-boiling-point substances to obtain the single-end hydroxyl silicone oil.
Preferably, in the preparation method, in the step (1), the dimethyl siloxane cyclic body is subjected to anhydrous treatment before the reaction, and more preferably, the anhydrous treatment is to remove water from the dimethyl siloxane cyclic body at the conditions of 60-70 ℃ and 0.086-0.1MPa of vacuum degree.
Preferably, in the above preparation method, in the step (2), the filtrate obtained in the step (1) is added dropwise to 95 to 123 parts by mass of an aqueous solution of sodium bicarbonate with a mass concentration of 5%, more preferably, the dropwise addition time is 15 to 20 min.
Preferably, in the above production method, in the step (2), the low boiling point substance is removed at 140 to 160 ℃ under a vacuum degree of 0.086 to 0.1 MPa.
Preferably, in the above preparation method, the hydrolysis treatment is performed using an aqueous sodium bicarbonate solution, and the reaction principle can be expressed by the following reaction equation:
m is 3, 4, 5, n is positive integer
The invention also provides single-terminal hydroxyl silicone oil which is prepared according to the preparation method.
The invention has the following beneficial effects:
1) the invention avoids the generation of a large amount of hydrochloric acid by-products in monomer hydrolysis in the common preparation method, has no post-treatment process and no pollution;
2) the method adopts a solid acid catalyst system, has high catalytic efficiency, can be directly filtered and separated after the reaction is finished, is simple to operate, and has environment-friendly catalyst which can be recycled for multiple times;
3) the invention fully utilizes the high activity of silicon-chlorine bonds to directly hydrolyze into silicon hydroxyl under mild conditions, avoids condensation among the silicon hydroxyl, has uniform and controllable product structure and high activity, and can be used for preparing high-performance organosilicon materials;
4) the method adopts a balance method to prepare the intermediate, has mature and reliable process, and can design and prepare the intermediate with different viscosities, thereby obtaining the single-end hydroxyl silicone oil with corresponding viscosity requirements;
5) the low-boiling-point substance produced by the invention is unreacted ring body, and can be used as raw material for the next production by simple dehydration treatment to remove trace CO2And no unusable by-products except NaCl.
Detailed Description
The present invention will be described in further detail with reference to specific examples, but the scope of the present invention is not limited thereto.
In the following examples, information on the raw materials used is shown in Table 1.
TABLE 1 type and manufacturer of raw materials and instruments
Example 1
Adding 480g of octamethylcyclotetrasiloxane into a 1L three-necked bottle, stirring, starting heating and raising the temperature to 60 ℃, starting vacuum, slowly closing a vacuum valve to enable the system pressure to reach-0.09 MPa, maintaining for 30min, removing the vacuum, adding 30g of HND-32 solid superacid and 5.5g of trimethylchlorosilane, and maintaining the temperature at 60 +/-5 ℃ for equilibrium reaction for 3 h. The mixture in the reaction flask was filtered with a buchner funnel to give a clear liquid. Preparing 500g of 5% sodium bicarbonate aqueous solution, adding the 5% sodium bicarbonate aqueous solution into a 1L three-necked bottle, starting stirring, dropwise adding the filtered clear solution into the three-necked bottle at room temperature, continuously stirring for 30min after 20min of dropwise addition is finished, standing, taking the supernatant into the 1L three-necked bottle, removing low boiling until no obvious liquid drips out under the conditions of 140 ℃ and-0.090 MPa, and obtaining colorless transparent liquid. The detection shows that the product has the refractive index of 1.406 and the viscosity of 130mm2(s) hydroxyl group content was 0.31%.
Example 2
210g of octamethylAdding cyclotetrasiloxane into a 500ml three-necked bottle, stirring, starting heating to raise the temperature to 65 ℃, starting vacuum, slowly closing a vacuum valve to enable the system pressure to reach-0.086 MPa, maintaining for 30min, removing the vacuum, adding 15g of HND-32 solid superacid and 10.8g of trimethylchlorosilane, and maintaining the temperature at 60 +/-5 ℃ for equilibrium reaction for 3 h. The mixture in the reaction flask was filtered with a buchner funnel to give a clear liquid. 200g of 5% sodium bicarbonate aqueous solution is prepared and added into a 1L three-necked bottle, stirring is started, filtered clear liquid is dropwise added into the three-necked bottle at room temperature, stirring is continued for 30min after 15min of dropwise addition is finished, standing is carried out, supernatant liquid is taken to be 500ml of three-necked bottle, low boiling is carried out under the conditions of 140 ℃ and-0.090 MPa until no obvious liquid is dripped out, and colorless transparent liquid is obtained. The detection shows that the product has a refractive index of 1.409 and a viscosity of 20mm2(s) hydroxyl group content 1.4%.
Example 3
Adding 407g of dimethyl siloxane mixed ring body into a 1L three-necked bottle, stirring, starting heating and raising the temperature to 60 ℃, starting vacuum, slowly closing a vacuum valve to enable the system pressure to reach-0.09 MPa, maintaining for 30min, removing the vacuum, adding 25g of HND-32 solid super acid and 10.8g of trimethylchlorosilane, and maintaining the temperature at 60 +/-5 ℃ for equilibrium reaction for 3 h. The mixture in the reaction flask was filtered with a buchner funnel to give a clear liquid. Preparing 500g of 5% sodium bicarbonate aqueous solution, adding the 5% sodium bicarbonate aqueous solution into a 1L three-necked bottle, starting stirring, dropwise adding the filtered clear solution into the three-necked bottle at room temperature, continuously stirring for 30min after 20min of dropwise addition, standing, taking the supernatant into the 1L three-necked bottle, and removing low boiling until no obvious liquid drips out under the conditions of 150 ℃ and-0.090 MPa to obtain colorless transparent liquid. The detection shows that the product has the refractive index of 1.408 and the viscosity of 50mm2(s) hydroxyl group content was 0.53%.
Example 4
Adding 300g of dimethyl siloxane mixed ring body into a 1L three-necked bottle, stirring, starting heating and raising the temperature to 60 ℃, starting vacuum, slowly closing a vacuum valve to enable the system pressure to reach-0.09 MPa, maintaining for 30min, removing the vacuum, adding 20g of HND-32 solid super acid and 2.2g of trimethylchlorosilane, maintaining the temperature at 60 +/-5 ℃ and carrying out equilibrium reaction for 3h. The mixture in the reaction flask was filtered with a buchner funnel to give a clear liquid. Preparing 300g of 5% sodium bicarbonate aqueous solution, adding the aqueous solution into a 1L three-necked bottle, starting stirring, dropwise adding the filtered clear solution into the three-necked bottle at room temperature, continuously stirring for 30min after 20min of dropwise addition, standing, taking the supernatant into the 1L three-necked bottle, removing low boiling under the conditions of 160 ℃ and-0.090 MPa until no obvious liquid is dripped out, and obtaining colorless transparent liquid. The detection shows that the product has a refractive index of 1.404 and viscosity of 350mm2(s) hydroxyl group content was 0.19%.
Example 5
Adding 470g of octamethylcyclotetrasiloxane into a 1L three-necked bottle, stirring, starting heating to raise the temperature to 65 ℃, starting vacuum, slowly closing a vacuum valve to enable the system pressure to reach-0.086 MPa, maintaining for 30min, removing the vacuum, adding 30g of HND-32 solid superacid and 1.7g of trimethylchlorosilane, and maintaining the temperature at 60 +/-5 ℃ for equilibrium reaction for 3 h. The mixture in the reaction flask was filtered with a buchner funnel to give a clear liquid. Preparing 500g of 5% sodium bicarbonate aqueous solution, adding the 5% sodium bicarbonate aqueous solution into a 1L three-necked bottle, starting stirring, dropwise adding the filtered clear solution into the three-necked bottle at room temperature, continuing stirring for 30min after 15min of dropwise addition is finished, standing, taking the supernatant into the 500ml three-necked bottle, and removing low boiling until no obvious liquid drips out under the conditions of 150 ℃ and-0.090 MPa to obtain colorless transparent liquid. The detection shows that the product has a refractive index of 1.400 and a viscosity of 1000mm2(s) hydroxyl group content was 0.09%.
Example 6
Adding 400g of octamethylcyclotetrasiloxane into a 1L three-necked bottle, stirring, starting heating and raising the temperature to 65 ℃, starting vacuum, slowly closing a vacuum valve to enable the system pressure to reach-0.086 MPa, maintaining for 30min, removing the vacuum, adding 30g of HND-32 solid superacid and 1.08g of trimethylchlorosilane, and maintaining the temperature at 60 +/-5 ℃ for equilibrium reaction for 3 h. The mixture in the reaction flask was filtered with a buchner funnel to give a clear liquid. Preparing 400g of 5% sodium bicarbonate water solution, adding into a 1L three-necked bottle, stirring, dripping the filtered clear liquid into the three-necked bottle at room temperature for 15min, stirring for 30min, standing, and collecting the supernatant to the 1L three-necked bottleAnd the mixture is boiled to be low under the condition of 145 ℃ and-0.090 MPa until no obvious liquid drips out, and colorless transparent liquid is obtained. The detection shows that the product has a refractive index of 1.400 and a viscosity of 1900mm2(s) hydroxyl group content was 0.04%.
Test example 1 vulcanization test
The single-terminal hydroxyl silicone oil prepared in example 1, example 4 and example 5 and the alpha, omega dihydroxy silicone oil with different viscosities are respectively subjected to a vulcanization experiment, and the specific test method is as follows:
adding 2 parts by weight of ethyl orthosilicate and 0.6 part by weight of dibutyltin dilaurate into 100 parts by weight of test silicone oil, uniformly stirring, and vulcanizing at room temperature for 72 hours to detect sulfide performance. The results of the experiment are shown in table 2.
TABLE 2 vulcanization test results of different test silicone oils
As can be seen from table 2, the single-terminal hydroxyl silicone oil prepared in the examples of the present invention, because it has only single-terminal hydroxyl group, can only form a viscous gel with almost no strength after vulcanization, and cannot form a completely vulcanized body with strength as the α, ω dihydroxy silicone oil.
Test example 2 preparation of dealcoholized RTV Silicone rubber
Single terminal hydroxyl silicone oil prepared by using example 1 and example 3 and 100mm2The dealcoholized single-component RTV silicone rubber sealant is prepared from dimethyl silicone oil with/s viscosity by the specific preparation method as follows:
100 parts by weight of 130000mm are introduced into a planetary stirrer2Alpha, omega-bis (methyldimethoxysiloxane) polydimethylsiloxane oil of viscosity/s, 1 part by weight of cyanoethyltrimethoxysilane; stirring for 10min, adding 33 weight parts of fumed silica, stirring for 45min, and adding 100 weight parts of 130000mm2And (3) continuously stirring alpha, omega-bis (methyldimethoxysiloxane) polydimethylsiloxane oil with viscosity/s for 15min, and then adding 40 parts by weight of test silicone oil to prepare the RTV base material. Mixing the above base material with 2 weight parts of methyltrimethoxysilane and 1 weight part ofKH560 (glycidyl ether oxypropyltrimethoxysilane) and 1 part by weight of dibutyltin dilaurate are mixed to prepare a dealcoholized single-component RTV silicone rubber sealant, and the performance of the sealant is tested after 7 days of vulcanization at room temperature. The results of the experiment are shown in table 3.
TABLE 3 Performance results of dealcoholized RTV silicone rubbers prepared from different experimental silicone oils
As can be seen from table 3, the single-terminal hydroxy silicone oil prepared in the examples of the present invention, when used as a diluent for a dealcoholized one-component RTV silicone rubber sealant, did not cause silicone oil bleeding and was useful in sealing applications where bleeding was not allowed.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (9)
1. A preparation method of single-end hydroxyl silicone oil is characterized in that dimethyl siloxane ring bodies and trimethyl chlorosilane are used as raw materials, equilibrium reaction is carried out under the catalysis of solid super acid, and the obtained reaction product is hydrolyzed.
2. The process according to claim 1, wherein 0.1 to 30 parts by weight of trimethylchlorosilane and 5 to 15 parts by weight of solid superacid are used per 100 parts by weight of dimethylsiloxane rings, and preferably 0.27 to 2.65 parts by weight of trimethylchlorosilane and 6.14 to 7.5 parts by weight of solid superacid are used per 100 parts by weight of dimethylsiloxane rings.
3. The production method according to claim 1 or 2, wherein the hydrolysis treatment is performed using an alkaline solution, and preferably, an alkaline compound of the alkaline solution is sodium bicarbonate.
4. The process according to any one of claims 1 to 3, wherein the temperature of the equilibration reaction is between 50 and 70 ℃, preferably the reaction time is between 3 and 4 h.
5. The production method according to any one of claims 1 to 4, wherein the dimethylsiloxane ring body is an octamethylcyclotetrasiloxane or a dimethylsiloxane mixed ring body.
6. The production method according to any one of claims 1 to 5, wherein the solid super acid is a sulfate ion acidic metal oxide type solid super acid, preferably a HND-32 solid super acid.
7. The production method according to any one of claims 1 to 6, comprising the steps of:
(1) mixing 100 parts by weight of dimethyl siloxane ring bodies, 5-15 parts by weight of solid super acid and 0.1-30 parts by weight of trimethylchlorosilane, reacting for 3-4 hours at 50-70 ℃, and filtering the product to obtain a filtrate;
(2) adding the filtrate obtained in the step (1) into 50-200 parts by mass of 3-8% sodium bicarbonate aqueous solution, reacting for a certain time, standing, taking supernatant, and removing low-boiling-point substances to obtain single-terminal hydroxyl silicone oil;
preferably, in step (1), the dimethylsiloxane ring bodies are subjected to anhydrous treatment before the reaction.
8. The production process according to any one of claims 1 to 7, wherein the hydrolysis treatment is carried out using an aqueous sodium hydrogencarbonate solution, and the reaction principle thereof can be represented by the following reaction equation:
9. a single-terminal hydroxy silicone oil characterized by being prepared by the preparation method according to any one of claims 1 to 8.
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| CN117757077A (en) * | 2024-01-09 | 2024-03-26 | 广州盛泰诺新材料科技有限公司 | Preparation method of high-activity single-end hydroxyl silicone oil |
Citations (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101508778A (en) * | 2009-03-11 | 2009-08-19 | 邬元娟 | Synthesis of polysiloxane containing bishydroxymethyl at single end |
| CN101580589A (en) * | 2009-06-25 | 2009-11-18 | 邬元娟 | Method for synthesizing polysiloxane having hydroxyethyl group at one end of molecule |
| JP2010144124A (en) * | 2008-12-22 | 2010-07-01 | Momentive Performance Materials Inc | Room temperature-curable polyorganosiloxane composition |
| CN102408567A (en) * | 2011-11-11 | 2012-04-11 | 杭州师范大学 | Preparation method for hydroxyl silicone oil |
| CN103421194A (en) * | 2013-07-08 | 2013-12-04 | 中科院广州化学有限公司 | Polyether type polyurethane prepolymer containing long lateral-chain organosilicon, and preparation method and application thereof |
| CN103483526A (en) * | 2013-08-20 | 2014-01-01 | 中科院广州化学有限公司 | Organic silicon graft modification polyester type polyurethane prepolymer and preparation and application thereof |
| CN103756326A (en) * | 2013-12-26 | 2014-04-30 | 惠州市永卓科技有限公司 | Oil-penetration prevention silicone gel and preparation method thereof |
| CN106146853A (en) * | 2016-06-30 | 2016-11-23 | 东莞市贝特利新材料有限公司 | LED liquid casting glue heat-resistant agent and preparation method thereof |
| CN107446134A (en) * | 2017-07-21 | 2017-12-08 | 大连大学 | A kind of synthetic method of single hydroxypropyl dimethyl silicone polymer |
| CN108137810A (en) * | 2015-11-04 | 2018-06-08 | 美国陶氏有机硅公司 | The method for preparing organosiloxane |
| JP2018131514A (en) * | 2017-02-14 | 2018-08-23 | 荒川化学工業株式会社 | Composition, cured product, thermally conductive coating, thermally conductive sheet, potting agent, and electronic component |
| CN109071821A (en) * | 2016-04-28 | 2018-12-21 | 住友化学株式会社 | Compound and containing compound composition |
| CN109438995A (en) * | 2018-12-21 | 2019-03-08 | 广州市白云化工实业有限公司 | The high-intensitive add-on type Silica hydrogel and preparation method thereof of hypotonic oil |
| CN109762340A (en) * | 2019-01-21 | 2019-05-17 | 东莞优邦材料科技股份有限公司 | A kind of activity silicone oil and its low pollution heat conductive silicone grease composition |
-
2019
- 2019-09-24 CN CN201910905269.7A patent/CN112625242B/en active Active
Patent Citations (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010144124A (en) * | 2008-12-22 | 2010-07-01 | Momentive Performance Materials Inc | Room temperature-curable polyorganosiloxane composition |
| CN101508778A (en) * | 2009-03-11 | 2009-08-19 | 邬元娟 | Synthesis of polysiloxane containing bishydroxymethyl at single end |
| CN101580589A (en) * | 2009-06-25 | 2009-11-18 | 邬元娟 | Method for synthesizing polysiloxane having hydroxyethyl group at one end of molecule |
| CN102408567A (en) * | 2011-11-11 | 2012-04-11 | 杭州师范大学 | Preparation method for hydroxyl silicone oil |
| CN103421194A (en) * | 2013-07-08 | 2013-12-04 | 中科院广州化学有限公司 | Polyether type polyurethane prepolymer containing long lateral-chain organosilicon, and preparation method and application thereof |
| CN103483526A (en) * | 2013-08-20 | 2014-01-01 | 中科院广州化学有限公司 | Organic silicon graft modification polyester type polyurethane prepolymer and preparation and application thereof |
| CN103756326A (en) * | 2013-12-26 | 2014-04-30 | 惠州市永卓科技有限公司 | Oil-penetration prevention silicone gel and preparation method thereof |
| CN108137810A (en) * | 2015-11-04 | 2018-06-08 | 美国陶氏有机硅公司 | The method for preparing organosiloxane |
| CN109071821A (en) * | 2016-04-28 | 2018-12-21 | 住友化学株式会社 | Compound and containing compound composition |
| CN106146853A (en) * | 2016-06-30 | 2016-11-23 | 东莞市贝特利新材料有限公司 | LED liquid casting glue heat-resistant agent and preparation method thereof |
| JP2018131514A (en) * | 2017-02-14 | 2018-08-23 | 荒川化学工業株式会社 | Composition, cured product, thermally conductive coating, thermally conductive sheet, potting agent, and electronic component |
| CN107446134A (en) * | 2017-07-21 | 2017-12-08 | 大连大学 | A kind of synthetic method of single hydroxypropyl dimethyl silicone polymer |
| CN109438995A (en) * | 2018-12-21 | 2019-03-08 | 广州市白云化工实业有限公司 | The high-intensitive add-on type Silica hydrogel and preparation method thereof of hypotonic oil |
| CN109762340A (en) * | 2019-01-21 | 2019-05-17 | 东莞优邦材料科技股份有限公司 | A kind of activity silicone oil and its low pollution heat conductive silicone grease composition |
Non-Patent Citations (2)
| Title |
|---|
| 王华金等: "固体超强酸催化制备小分子羟基硅油工艺研究", 《东山化工》 * |
| 赵倩: "固体超强酸SO42-/ZrO2-A12O3 催化反应", 《广东化工》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117757077A (en) * | 2024-01-09 | 2024-03-26 | 广州盛泰诺新材料科技有限公司 | Preparation method of high-activity single-end hydroxyl silicone oil |
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