CN103524740A - Preparation method of methyl phenyl hydroxyl silicone oil with low tetracyclic compound content - Google Patents
Preparation method of methyl phenyl hydroxyl silicone oil with low tetracyclic compound content Download PDFInfo
- Publication number
- CN103524740A CN103524740A CN201310211720.8A CN201310211720A CN103524740A CN 103524740 A CN103524740 A CN 103524740A CN 201310211720 A CN201310211720 A CN 201310211720A CN 103524740 A CN103524740 A CN 103524740A
- Authority
- CN
- China
- Prior art keywords
- low
- preparation
- aminomethyl phenyl
- silicon oil
- hydroxy silicon
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Landscapes
- Silicon Polymers (AREA)
Abstract
The invention provides a preparation method of methyl phenyl hydroxyl silicone oil with low tetracyclic compound content. The preparation method comprises the following steps: with 1,3,5-trimethyl-1,3,5-triphenyl trisiloxane as a raw material and lithium hydroxide as a catalyst, adding water as an end-capping agent, carrying out a reaction in an organic solvent for 0.1-24 hours at the temperature ranging from -20 DEG C to 100 DEG C, then neutralizing by using acid, and removing the organic solvent, so that the methyl phenyl hydroxyl silicone oil with low tetracyclic compound content is obtained, wherein a tetracyclic compound is 1,3,5,7-tetramethyl-1,3,5,7-tetraphenyl tetracyclic siloxane. The preparation method of the methyl phenyl hydroxyl silicone oil with low tetracyclic compound content is simple in technology, and the methyl phenyl hydroxyl silicone oil product with low tetracyclic compound content has lower viscosity, higher purity and low tetracyclic compound content and can better meet a practical application requirement.
Description
Technical field
The present invention relates to organosilicon technical field, relate in particular to the preparation method of the aminomethyl phenyl hydroxy silicon oil of a kind of low Fourth Ring body burden.
Background technology
Methyl phenyl silicone oil is the product of part methyl after being substituted by phenyl in dimethyl silicone oil.After methyl is substituted by phenyl, than the dimethyl silicone oil with viscosity, there is higher viscosity-temperature coefficient, lower zero pour, flash-point, the variation of anti-compression properties viscosity under pressure is faster, has good oxidative stability, thermotolerance, radiation-resistant property, flame resistivity and ultraviolet-resistent property etc.The performance of methyl phenyl silicone oil excellence makes it can be applied to the various fields of national life and production, can be used as the carrier of lubricating oil, transformer oil, gas liqud chromatography, shockproof, dustproof, insulation, damping and high-temperature heat carrier etc., is the liquid damping dielectric liquid of ideal of electronic instrument.Wherein, hydroxy-end capped methyl phenyl silicone oil can significantly improve slipperiness and the kindliness of fabric during as fabric finishing agent, and gives the hydrophobic oil repellent that fabric is good.Thereby low-molecular-weight aminomethyl phenyl hydroxy silicon oil can be used for the anti-stick processing of paper etc., as the raw material of the PSI of synthetic high molecular, prepare constitution controller in silicon rubber process, add and in silicon rubber, as coating, possess anti-soil erosion resistance etc. on a small quantity.Therefore, aminomethyl phenyl hydroxy silicon oil has good application prospect and market, and its technology of preparing has also caused that people study interest greatly.
Chinese patent CN1044100A discloses a kind of α, the method for making of ω siloxane glycol, and this invention adopts intermediate water solution to use (RO)
2si (RO)
2siR ' R " (R is Me, Et; R ', R " be respectively H, Me, Et, Ph, Vi etc.) in excessive water hydrolysis prepare the method for hydroxy silicon oil, catalyzer hydrochloric acid consumption is water consumption 0.05～1%, carries out at normal temperatures 1～20min and can complete reaction; In products therefrom, alkoxyl group has almost all been hydrolyzed, and remaining quantity is lower than 0.2%, and the polymerization degree is 2～10, hydroxy radical content 14%.Because this method is the preparation of organoalkoxysilane hydrolysis method, therefore from the polymerization degree and hydroxy radical content analysis, hydroxy silicon oil prepared by this method contains dimethyl silica chain.
US Patent No. 4066680 discloses a kind of α, the building-up process of ω-silicone glycol, and this invention adopts two-step approach to take acidic white earth to have prepared the α of the polymerization degree 6～7, w-silicone glycol: first, mix annular siloxane (R as catalyzer
2siO)
3(R=CH
3, CH=CH
2, Ph) and the catalyzer 4h that refluxes in aceticanhydride and glacial acetic acid, generate intermediate product acetoxysilane, add subsequently sodium bicarbonate aqueous solution hydrolysis preparation, but this method be take acid as catalyzer, when R is Ph, that synthetic is α, ω-phenylbenzene silicone glycol.
Chinese patent ZL200710068595.4 discloses a kind of preparation method of hydroxyl-terminated polymethylphenyl sioxane, with hydroxy-end capped polydimethylsiloxane, methyl phenyl ring siloxane and Tetramethylammonium hydroxide are raw material, choose different ratios, by polycondensation, prepare hydroxy-end capped PSI.Hydroxyl-terminated polymethylphenyl sioxane prepared by this method is hydroxy-end capped with dimethyl-silicon, containing dimethyl silica chain.
Ger.Offen2403303 has reported with chlorosilane R
nsiX
4-n(wherein R is Me, Et, Ph or Vi, X=Cl, n=2～3) is at NH
2-NH
4in Cl solution, be hydrolyzed, can make the α of SiOH content 22.4%, ω siloxane glycol.
Chinese patent ZL201110390725.2 discloses a kind of method that direct hydrolysis dichloromethyl phenylsilane is prepared low viscosity aminomethyl phenyl hydroxy silicon oil, has that speed of response is fast, reaction conditions is gentle, simple operation and other advantages.But the method that the chlorosilane of take is raw material hydrolysis preparation, all produces hydrogenchloride in reaction process, equipment and technique are had to higher requirement.
US Patent No. 2258222 discloses a kind of by hydroxy-end capped 1,2-dimethyl-1,2-phenylbenzene sily oxide, hydroxy-end capped 1,2,3-trimethylammonium-1,2,3-triphenyl trisiloxanes and aminomethyl phenyl cyclotrisiloxane mix in toluene, at 120 ℃ of heating 30min desolvations, are heated to subsequently 175 ℃ and carry out polymerization, reaction times is longer, and gained methyl phenyl silicone oil viscosity is larger.But methyl phenyl silicone oil molecular weight prepared by this method is high, viscosity is large.
Because methyl phenyl silicone is easily converted into the equilibrium system containing Fourth Ring body under catalyzer exists, thereby affect the purity of product, but mostly do not address the Fourth Ring body burden in product in above-mentioned report.Because Fourth Ring body has very high boiling point, physicals is close with product again, is difficult to adopt physics, chemical process separated from product, thereby causes product to be restricted in the application in the fields such as Polymer Synthesizing, the control of high temperature silicon rubber structure.Summary of the invention
For solving methyl phenyl silicone, under existing, catalyzer is easily converted into the equilibrium system containing Fourth Ring body, thereby affect the problem of the purity of product, the present invention proposes the preparation method of the aminomethyl phenyl hydroxy silicon oil of a kind of low Fourth Ring body burden, technique of the present invention is simple, product has lower viscosity and higher purity, Fourth Ring body burden is low, more can adapt to the demand of practical application.
The present invention is achieved by the following technical solutions: the preparation method of the aminomethyl phenyl hydroxy silicon oil of a kind of low Fourth Ring body burden, with 1,3,5-trimethylammonium-1,3,5-triphenyl cyclotrisiloxane is raw material, take lithium hydroxide as catalyzer, add water as end-capping reagent, in organic solvent, react, temperature of reaction is at-20 ℃～100 ℃, reaction times is 0.1～24h, then with acid neutralization, then removes organic solvent, obtain the aminomethyl phenyl hydroxy silicon oil of low Fourth Ring body burden, described aminomethyl phenyl hydroxy silicon oil general formula is
m=3～30, m is the polymerization degree.
Described 1,3,5-trimethylammonium-1, the structural formula of 3,5-triphenyl cyclotrisiloxane is:
Described Fourth Ring body is 1,3,5,7-tetramethyl--1,3,5,7-tetraphenyl cyclotetrasiloxane.The present invention has suppressed the generation of Fourth Ring body from synthesis technique, obtains the aminomethyl phenyl hydroxy silicon oil of low Fourth Ring body burden, has improved the quality of product, expands its Application Areas.
The mass parts of reactant is: 1,3,5-trimethylammonium-1, and 100 parts of 3,5-triphenyl cyclotrisiloxane, 0.1～20 part, water, 0.01～20 part of lithium hydroxide, 100～500 parts of organic solvents, as preferably, described lithium hydroxide consumption is: 0.01～5 part.
Described organic solvent is a kind of in acetonitrile, dioxane, tetrahydrofuran (THF), glycol dimethyl ether, ethyl acetate, espeleton, and as preferably, described organic solvent is dioxane.
As preferably, temperature of reaction is-20 ℃～50 ℃, and the reaction times is 0.1～8h.
As preferably, reaction vessel is with stirring, thermometer, reflux condensate device.
While removing organic solvent, temperature is risen to 35～150 ℃, under 1.33kPa pressure, keep 0.5～3h that organic solvent is removed, as preferably, use vacuum pump to remove organic solvent.
Compared with prior art, the invention has the beneficial effects as follows:
(1) technique of the present invention is simple, and controllability is strong;
(2) reaction conversion ratio is high, and product has lower viscosity and higher purity, 1,3,5,7-tetramethyl--1, and 3,5,7-tetraphenyl cyclotetrasiloxane content is low, and its numerical value, lower than 3%, more can adapt to the demand of practical application;
(3) selected catalyzer, end-capping reagent is cheap, is applicable to the needs of industrial large-scale production.
Embodiment
Below by embodiment, the present invention is described in further detail.This embodiment can make the present invention of those skilled in the art comprehend, but does not limit the present invention in any way.
Embodiment 1
By 1,3,5-trimethylammonium-1,3,5-triphenyl cyclotrisiloxane 50g, water 0.05g, lithium hydroxide 0.02g and dioxane 50g, put in the reaction vessel that stirring, thermometer, reflux condensate device are housed and fully mix, and controlling temperature of reaction is 5 ℃, reaction times is used in glacial acetic acid and arrives neutral with above-mentioned reaction solution after being 8h; Reaction solution is poured in the there-necked flask with water distilling apparatus, started vacuum pump, be warming up to 60 ℃ and keep 0.5h that organic solvent is removed under 1.33kPa pressure, obtain the aminomethyl phenyl hydroxy silicon oil 1 of low Fourth Ring body burden.
By analysis: the viscosity of the aminomethyl phenyl hydroxy silicon oil 1 of low Fourth Ring body burden is 760mPas, Fourth Ring body burden 1.9%.
Embodiment 2
By 1,3,5-trimethylammonium-1,3,5-triphenyl cyclotrisiloxane 50g, water 0.05g, lithium hydroxide 0.2g and dioxane 100g, put in the reaction vessel that stirring, thermometer, reflux condensate device are housed and fully mix; Controlling temperature of reaction is 50 ℃, and the reaction times is 0.5h; With arriving neutral with above-mentioned reaction solution in glacial acetic acid; Reaction solution is poured in the there-necked flask with water distilling apparatus, started vacuum pump, be warming up to 35 ℃ and keep 3h that organic solvent is removed under 1.33kPa pressure, obtain the aminomethyl phenyl hydroxy silicon oil 2 of low Fourth Ring body burden.
By analysis: the viscosity of the aminomethyl phenyl hydroxy silicon oil 2 of low Fourth Ring body burden is 980mPas, Fourth Ring body burden 2.4%.
Embodiment 3
By 1,3,5-trimethylammonium-1,3,5-triphenyl cyclotrisiloxane 50g, water 0.05g, lithium hydroxide 0.005g and dioxane 150g, put in the reaction vessel that stirring, thermometer, reflux condensate device are housed and fully mix; Controlling temperature of reaction is 100 ℃, and the reaction times is 0.1h; With in glacial acetic acid and the above-mentioned neutrality that is reacted to; Reaction solution is poured in the there-necked flask with water distilling apparatus, started vacuum pump, be warming up to 60 ℃ and keep 2h that organic solvent is removed under 1.33kPa pressure, obtain the aminomethyl phenyl hydroxy silicon oil 3 of low Fourth Ring body burden.
By analysis: the viscosity of the aminomethyl phenyl hydroxy silicon oil 3 of low Fourth Ring body burden is 360mPas, Fourth Ring body burden 1.8%.
Embodiment 4
By 1,3,5-trimethylammonium-1,3,5-triphenyl cyclotrisiloxane 50g, water 0.5g, lithium hydroxide 2.5g and dioxane 100g, put in the reaction vessel that stirring, thermometer, reflux condensate device are housed and fully mix; Controlling temperature of reaction is 20 ℃, and the reaction times is 2h; With arriving neutral with above-mentioned reaction solution in glacial acetic acid; Reaction solution is poured in the there-necked flask with water distilling apparatus, started vacuum pump, be warming up to 60 ℃ and keep 0.5h that organic solvent is removed under 1.33kPa pressure, obtain the aminomethyl phenyl hydroxy silicon oil 4 of low Fourth Ring body burden.
By analysis: the viscosity of the aminomethyl phenyl hydroxy silicon oil 4 of low Fourth Ring body burden is 690mPas, Fourth Ring body burden 2.1%.
Embodiment 5
By 1,3,5-trimethylammonium-1,3,5-triphenyl cyclotrisiloxane 50g, water 5g, lithium hydroxide 0.02g and dioxane 50g, put in the reaction vessel that stirring, thermometer, reflux condensate device are housed and fully mix; Controlling temperature of reaction is 0 ℃, and the reaction times is 5h; With arriving neutral with above-mentioned reaction solution in glacial acetic acid; Reaction solution is poured in the there-necked flask with water distilling apparatus, started vacuum pump, be warming up to 150 ℃ and keep 0.1h that organic solvent is removed under 1.33kPa pressure, obtain the aminomethyl phenyl hydroxy silicon oil 5 of low Fourth Ring body burden.
By analysis: the viscosity of the aminomethyl phenyl hydroxy silicon oil 5 of low Fourth Ring body burden is 460mPas, Fourth Ring body burden 2.9%.
Embodiment 6
By 1,3,5-trimethylammonium-1,3,5-triphenyl cyclotrisiloxane 50g, water 5g, lithium hydroxide 0.2g and dioxane 150g, put in the reaction vessel that stirring, thermometer, reflux condensate device are housed and fully mix; Controlling temperature of reaction is-20 ℃, and the reaction times is 4h; With arriving neutral with above-mentioned reaction solution in glacial acetic acid; Reaction solution is poured in the there-necked flask with water distilling apparatus, started vacuum pump, be warming up to 60 ℃ and keep 1h that organic solvent is removed under 1.33kPa pressure, obtain the aminomethyl phenyl hydroxy silicon oil 6 of low Fourth Ring body burden.
By analysis: the viscosity of the aminomethyl phenyl hydroxy silicon oil 6 of low Fourth Ring body burden is 330mPas, Fourth Ring body burden 1.5%.
Embodiment 7
By 1,3,5-trimethylammonium-1,3,5-triphenyl cyclotrisiloxane 50g, water 10g, lithium hydroxide 0.5g and glycol dimethyl ether 250g, put in the reaction vessel that stirring, thermometer, reflux condensate device are housed and fully mix; Controlling temperature of reaction is 20 ℃, and the reaction times is 8h; With arriving neutral with above-mentioned reaction solution in glacial acetic acid; Reaction solution is poured in the there-necked flask with water distilling apparatus, started vacuum pump, be warming up to 80 ℃ and keep 3h that organic solvent is removed under 1.33kPa pressure, obtain the aminomethyl phenyl hydroxy silicon oil 7 of low Fourth Ring body burden.
By analysis, the viscosity of the aminomethyl phenyl hydroxy silicon oil 7 of low Fourth Ring body burden is 420mPas, Fourth Ring body burden 2.1%.
Embodiment 8
By 1,3,5-trimethylammonium-1,3,5-triphenyl cyclotrisiloxane 100g, water 0.2g, lithium hydroxide 0.01g and tetrahydrofuran (THF) 150g, put in the reaction vessel that stirring, thermometer, reflux condensate device are housed and fully mix; Controlling temperature of reaction is 10 ℃, and the reaction times is 24h; With arriving neutral with above-mentioned reaction solution in glacial acetic acid; Reaction solution is poured in the there-necked flask with water distilling apparatus, started vacuum pump, be warming up to 60 ℃ and keep 1h that organic solvent is removed under 1.33kPa pressure, obtain the aminomethyl phenyl hydroxy silicon oil 8 of low Fourth Ring body burden.
By analysis, the viscosity of the aminomethyl phenyl hydroxy silicon oil 8 of low Fourth Ring body burden is 380mPas, Fourth Ring body burden 1.8%.
Claims (6)
1. a preparation method for the aminomethyl phenyl hydroxy silicon oil of low Fourth Ring body burden, is characterized in that, with 1,3,5-trimethylammonium-1,3,5-triphenyl cyclotrisiloxane is raw material, take lithium hydroxide as catalyzer, adds water as end-capping reagent, in organic solvent, react, temperature of reaction is at-20 ℃～100 ℃, and the reaction times is 0.1～24h, then with acid neutralization, arrive neutral, remove organic solvent again, obtain the aminomethyl phenyl hydroxy silicon oil of low Fourth Ring body burden, described aminomethyl phenyl hydroxy silicon oil general formula is:
2. the preparation method of the aminomethyl phenyl hydroxy silicon oil of a kind of low Fourth Ring according to claim 1 body burden, it is characterized in that, the mass parts of reactant is: 1,3,5-trimethylammonium-1,3,100 parts of 5-triphenyl cyclotrisiloxane, 0.1～20 part, water, 0.01～20 part of lithium hydroxide, 100～500 parts of organic solvents.
3. the preparation method of the aminomethyl phenyl hydroxy silicon oil of a kind of low Fourth Ring according to claim 1 and 2 body burden, it is characterized in that, described organic solvent is a kind of in acetonitrile, dioxane, tetrahydrofuran (THF), glycol dimethyl ether, ethyl acetate, espeleton.
4. the preparation method of the aminomethyl phenyl hydroxy silicon oil of a kind of low Fourth Ring according to claim 3 body burden, is characterized in that, described organic solvent is dioxane.
5. the preparation method of the aminomethyl phenyl hydroxy silicon oil of a kind of low Fourth Ring according to claim 1 body burden, is characterized in that, temperature of reaction is-20 ℃～50 ℃, and the reaction times is 0.1～8h.
6. the preparation method of the aminomethyl phenyl hydroxy silicon oil of a kind of low Fourth Ring according to claim 1 body burden, is characterized in that, the step that removes organic solvent is: temperature is risen to 35～150 ℃, under 1.33kPa pressure, keep 0.5～3h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310211720.8A CN103524740B (en) | 2013-05-31 | 2013-05-31 | The preparation method of the aminomethyl phenyl hydroxy silicon oil of a kind of low Fourth Ring body burden |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310211720.8A CN103524740B (en) | 2013-05-31 | 2013-05-31 | The preparation method of the aminomethyl phenyl hydroxy silicon oil of a kind of low Fourth Ring body burden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103524740A true CN103524740A (en) | 2014-01-22 |
| CN103524740B CN103524740B (en) | 2015-09-09 |
Family
ID=49927122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310211720.8A Active CN103524740B (en) | 2013-05-31 | 2013-05-31 | The preparation method of the aminomethyl phenyl hydroxy silicon oil of a kind of low Fourth Ring body burden |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103524740B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105131295A (en) * | 2015-08-26 | 2015-12-09 | 广州市白云化工实业有限公司 | Phenyl hydroxyl silicone oil and preparation method and application thereof |
| CN107501506A (en) * | 2017-08-15 | 2017-12-22 | 杭州吉华高分子材料股份有限公司 | A kind of high-temperature resistant waterborne polyurethane and preparation method thereof |
| CN113754888A (en) * | 2020-06-02 | 2021-12-07 | 赢创运营有限公司 | Linear acetoxy-containing siloxanes and derivatives |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101074283A (en) * | 2007-05-22 | 2007-11-21 | 杭州师范大学 | Method for producing hydroxy-end capped polymethylphenylsilixane |
-
2013
- 2013-05-31 CN CN201310211720.8A patent/CN103524740B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101074283A (en) * | 2007-05-22 | 2007-11-21 | 杭州师范大学 | Method for producing hydroxy-end capped polymethylphenylsilixane |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105131295A (en) * | 2015-08-26 | 2015-12-09 | 广州市白云化工实业有限公司 | Phenyl hydroxyl silicone oil and preparation method and application thereof |
| CN105131295B (en) * | 2015-08-26 | 2018-02-13 | 广州市白云化工实业有限公司 | Phenyl hydroxy silicon oil and its preparation method and application |
| CN107501506A (en) * | 2017-08-15 | 2017-12-22 | 杭州吉华高分子材料股份有限公司 | A kind of high-temperature resistant waterborne polyurethane and preparation method thereof |
| CN113754888A (en) * | 2020-06-02 | 2021-12-07 | 赢创运营有限公司 | Linear acetoxy-containing siloxanes and derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103524740B (en) | 2015-09-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103333338B (en) | A kind of vinyl silicone oil and synthetic method thereof | |
| CN103865389B (en) | A kind of using method of add-on type solvent-free organic silicon interleaving agent | |
| JP5905125B2 (en) | Method for producing polysilsesquioxane using carbon dioxide solvent and polysilsesquioxane | |
| CN103642046B (en) | A kind of preparation method of end-vinyl fluorosilicon oil | |
| CN104086772A (en) | Uramido modified MQ silicon resin, and preparation method and application thereof | |
| CN107459652B (en) | Heat-resistant silicone resin capable of being cured at room temperature and preparation method thereof | |
| CN102516546B (en) | Preparation method for low-viscosity methyl phenyl hydroxyl silicone oil | |
| CN104371107A (en) | Hydrogen-containing MQ silicon resin and preparation method thereof | |
| CN103044683A (en) | Modified MQ silicone resin and preparation method thereof | |
| CN103524740B (en) | The preparation method of the aminomethyl phenyl hydroxy silicon oil of a kind of low Fourth Ring body burden | |
| CN110256677B (en) | Epoxy modified trifluoropropyl silicone oil and preparation method thereof | |
| CN101781328B (en) | Preparation method of cyclosiloxane | |
| KR20140024244A (en) | Hydrosilicone resin and preparation process thereof | |
| CN109912801A (en) | One kind siloxanes of functional poly containing quaternary ammonium salt and its synthetic method | |
| CN107459651A (en) | Organopolysiloxane resins and preparation method thereof | |
| CN105778096B (en) | The manufacturing method and application of the silicone resin of alkenyl containing benzocyclobutane | |
| CN108329474B (en) | Organic silicon resin for single-component addition type organic silicon impregnating varnish and preparation method and application thereof | |
| CN103450481A (en) | Preparation method of methyl phenyl vinyl silicone | |
| JP6146856B2 (en) | Polysilsesquioxane liquid, polysilsesquioxane glass and method for producing the same | |
| CN104558611A (en) | MDTQ silicon resin, as well as preparation method and application thereof | |
| CN104829839B (en) | A kind of fluoro organosilicon polymer and preparation method thereof | |
| CN104119535A (en) | Preparation method of hydroxyl-terminated fluorosilicone crude rubber | |
| CN104610546B (en) | Preparation method of annular reticular silicon resin | |
| CN105368068A (en) | High-temperature-resistant, high-breakdown-voltage and filler-free organic silicone rubber for sleeve | |
| CN105085567B (en) | Cyclosiloxane that polyfunctional group substitutes altogether, ring siloxane mixture and its preparation method and application |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20220624 Address after: 311300 Qingyun Village Industrial Park, Taihuyuan Town, Lin'an District, Hangzhou City, Zhejiang Province Patentee after: HANGZHOU KEJIA NEW MATERIALS Co.,Ltd. Address before: 310036 No. 16 Xuelin Road, Xiasha Economic Development Zone, Hangzhou City, Zhejiang Province Patentee before: Hangzhou Normal University |