CN104403105A - Preparation method of phenyl vinyl silicone oil with controlled refractive index - Google Patents
Preparation method of phenyl vinyl silicone oil with controlled refractive index Download PDFInfo
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Abstract
The invention discloses a preparation method of phenyl vinyl silicone oil with a controlled refractive index. The preparation method sequentially comprises the following steps of allowing a monomer, an end capping reagent and a catalyst to carry out ring-opening polymerization balanced reaction for 3.0-5.0h at 100-140 DEG C in an inert gas atmosphere, heating to 150-170 DEG C, keeping the temperature constant for a period of time to decompose the catalyst, further heating to 190-210 DEG C, and removing a low-boiling-point substance at a vacuum degree from -0.090 to -0.100MPa till no fraction flows out. The prepared phenyl vinyl silicone oil has the advantages of high light transmittance, and controlled refractive index and viscosity as well as outstanding performances such as high reactivity, radiation resistance, high and low temperature resistance and the like, is particularly applicable to LED (light-emitting diode) organic silicon packaging materials, and can effectively improve luminous efficiency of the LED organic silicon packaging materials and reduce energy consumption.
Description
Technical field
The present invention relates to a kind of preparation method of vinyl silicone oil, particularly relate to the preparation method of the controlled phenyl-vinyl silicon oil of a kind of refractive index.
Background technology
In organosilicon product, silicone oil of a great variety, wherein phenyl silicone oil is one of its principal item.Phenyl silicone oil possesses insulativity, ozone resistants, hydrophobic protection against the tide, high-low temperature resistant and radioresistance, is widely used in the fields such as electronics, machinery and cosmetics of everyday use.In additional organosilicon material, the refractive index of phenyl-vinyl silicon oil is high, is conducive to the output of light, thus becomes the base polymer of LED encapsulation material first-selection.Traditional phenyl silicone oil is connected with two methyl for repeating unit same Siliciumatom to be connected with on two phenyl and same Siliciumatom, if with solid-state octaphenylcyclotetrasiloxane and liquid octamethylcyclotetrasiloxane for monomer prepares phenyl-vinyl silicon oil, because the compatibility of two kinds of monomers is poor, copolymerization is difficult to uniform alternating copolymerization.The product prepared of this method in view of the refractive index of segment different in molecular chain different, the phenyl-vinyl silicon oil transparency thus obtained is poor.The structure mainly dimethyl diphenyl silicone oil of domestic phenyl silicone oil, it is by hydrolysis such as phenylbenzene dialkoxy silicane, diphenyl dichlorosilane, dialkyl dialkoxy silicanes, again through base catalyzed condensation, the skill of the preparation of this type of phenyl silicone oil is loaded down with trivial details, cost is high and efficiency is low.
The report of the more existing preparation method about phenyl-vinyl silicon oil is also not all roses.As used the oxyhydroxide such as potassium hydroxide for catalyzer, then need the aftertreatments such as acid neutralization, filtration and washing, the residual inorganic salt in its phenyl-vinyl silicon oil are not easily removed, and affect the quality of product.Patent CN201210484765.8 report use phenyl alkoxysilane and alkyl-dialkoxysilanes hydrolytic condensation polymerization prepare phenyl-vinyl silicon oil, it mainly comprises acid hydrolysis, base catalysis, acid neutralization and the step such as filtration, and this method steps preparing phenyl-vinyl silicon oil is tediously long, control that difficulty is high, production efficiency is low and waste water resource.Meanwhile, its molecular structure is wayward, can affect stability in storage and the transmittance of product.In addition, have report to mention, when phenyl content is identical, the phenyl-vinyl silicon oil containing phenylbenzene chain link possesses higher viscosity than the phenyl-vinyl silicon oil containing aminomethyl phenyl chain link.Thus by above-mentioned preparation method prepare containing the phenyl-vinyl silicon oil of phenylbenzene chain link, not easily obtain the high and product of modest viscosity of phenyl content.
Summary of the invention
A kind of simple operation, the efficiently controlled and preparation method of environment amenable phenyl-vinyl silicon oil are the object of this invention is to provide, the phenyl-vinyl silicon oil light transmission of gained is high, refractive index and viscosity size controlled, be highly suitable for the fields such as LED encapsulation material.
The present invention is by the following technical solutions: the preparation method of the phenyl-vinyl silicon oil that a kind of refractive index is controlled, comprises the following steps:
(1) under protection of inert gas, by the monomer of 100 weight parts, the end-capping reagent of 0.5 ~ 5.0 weight part, the catalyst mix of 0.5-1.5 weight part evenly after, 100 ~ 140
oring-opening polymerization 3.0 ~ 5.0 hours under C; Described monomer is the cyclosiloxane monomer containing phenyl, or the mix monomer for being made up of according to any proportioning with the cyclosiloxane monomer containing phenyl methyl cyclosiloxane monomer; Described end-capping reagent is selected from divinyl tetramethyl disiloxane, Vinyldimethylethoxysilane, hexamethyldisiloxane or dimethylvinylmethoxysiiane; Described catalyzer is selected from five water Tetramethylammonium hydroxide, tetramethyl ammonium hydroxide solution, trimethyl ammonium hydroxide, Tetramethylammonium hydroxide alkali glue, trimethyl ammonium hydroxide alkali glue;
(2) by the product after step (1) ring-opening polymerization 150 ~ 170
odecomposition catalyst 1-2h under the condition of C, protection of inert gas;
(3) product after step 2 being processed is at 190-210
oc, vacuum tightness are under the condition of-0.09 ~-0.10MPa, remove low-boiling-point substance, until flow out without cut; By removing after the product after low-boiling-point substance is cooled to room temperature, obtain the phenyl-vinyl silicon oil that refractive index is controlled.
Further, the described cyclosiloxane monomer containing phenyl comprises aminomethyl phenyl cyclotrisiloxane, aminomethyl phenyl cyclotetrasiloxane, aminomethyl phenyl D5, aminomethyl phenyl-dimethicone; Described methyl cyclosiloxane monomer comprises hexamethyl cyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentaandoxane, ten diformazan basic ring six siloxanes, t etram-ethyltetravinylcyclotetrasiloxane.
Further, described monomer obtains through dehydration pre-treatment, and pretreated temperature of dewatering is 50-70
oc, vacuum tightness is 0.09 ~ 0.10MPa.
The invention has the beneficial effects as follows: the present invention adopts the monomers such as dimethicone, aminomethyl phenyl-dimethicone monomer to be raw material, this several monomer compatibility is good, product aminomethyl phenyl chain link is evenly distributed in the molecular chain of phenyl-vinyl silicon oil, avoids the drawbacks such as the system muddiness that the narrow and high phenyl content of adopt phenylbenzene chain link to prepare the too high Application Areas of viscosity that phenyl-vinyl silicon oil brings causes.Preparation process of the present invention is solvent-free, environmentally friendly and the transmittance of product is high, is convenient to the silicone oil preparing high phenyl content and modest viscosity.Product of the present invention possesses that productive rate is high, viscosity and refractive index are easy to the advantages such as adjustment, is specially adapted to the encapsulation of optical electron element.In addition, abundant raw material of the present invention, technique is simple, easily control, non-corrosiveness and environmentally friendly, is convenient to industrialization.
Embodiment
Below in conjunction with embodiment, the present invention will be further explained.Following examples only for illustration of the present invention, but are not used for limiting working of an invention scope.
A preparation method for the phenyl-vinyl silicon oil that refractive index is controlled, this method can by the refractive index regulating the content of each monomer participating in reaction to regulate product, and preparation method comprises the following steps:
(1) under protection of inert gas, by the monomer of 100 weight parts, the end-capping reagent of 0.5-5.0 weight part, the catalyst mix of 0.5-1.5 weight part evenly after, at 100-140
oring-opening polymerization 3.0-5.0 hour under C; Described monomer is the cyclosiloxane monomer containing phenyl, or containing the cyclosiloxane monomer of phenyl and the mix monomer formed according to any proportioning of methyl cyclosiloxane monomer; Described end-capping reagent is selected from divinyl tetramethyl disiloxane, Vinyldimethylethoxysilane, hexamethyldisiloxane or dimethylvinylmethoxysiiane; Described catalyzer is selected from five water Tetramethylammonium hydroxide, tetramethyl ammonium hydroxide solution, trimethyl ammonium hydroxide, Tetramethylammonium hydroxide alkali glue, trimethyl ammonium hydroxide alkali glue;
The described cyclosiloxane monomer containing phenyl comprises aminomethyl phenyl cyclotrisiloxane, aminomethyl phenyl cyclotetrasiloxane, aminomethyl phenyl D5, aminomethyl phenyl-dimethicone; Described methyl cyclosiloxane monomer comprises hexamethyl cyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentaandoxane, ten diformazan basic ring six siloxanes, t etram-ethyltetravinylcyclotetrasiloxane.
Described monomer can be obtained by dehydration pre-treatment, and pretreated temperature of dewatering is 50-70
oc, vacuum tightness is 0.09 ~ 0.10MPa.
(2) by the product after step (1) ring-opening polymerization at 150-170
odecomposition catalyst 1-2h under the condition of C, protection of inert gas;
(3) product after catalyzer will be removed at 190-210
oc, vacuum tightness are under the condition of-0.09 ~-0.10MPa, remove low-boiling-point substance, until flow out without cut; By removing after the product after low-boiling-point substance is cooled to room temperature, obtain the phenyl-vinyl silicon oil that refractive index is controlled.
Below in conjunction with embodiment, the invention will be further described, participating in reaction monomers kind and ratio, being controlled within the scope of 1.43-1.55 by the refractive index of product by regulating.
embodiment 1
Be equipped with in the there-necked flask of the 500ml of whipping appts, condenser system and thermometer at one and add 100.0g methyl phenyl ring siloxane and 100.0g octamethylcyclotetrasiloxane, 60
oc, vacuum tightness are under-0.090MPa, and constant temperature for some time fully dewaters; Add 1.0g divinyl tetramethyl disiloxane and be roughly equal to the alkali glue of the Tetramethylammonium hydroxide having 100ppm, stir; Under protection of inert gas, be warmed up to 100
oc, balanced reaction 5.0 hours; Be warmed up to 150 again
oc decomposition catalyst, maintains for some time; Be warmed up to 200 further
oc is under the condition of-0.090MPa in vacuum tightness, removes low-boiling-point substance extremely without obvious cut, then room temperature during vacuum cooling.
Detected result: product is transparent, productive rate higher than 90%, viscosity be about 6500mpa higher than, refractive index is 1.472, and volatile matter is lower than 1.0%.
embodiment 2
Be equipped with in the there-necked flask of the 500ml of whipping appts, condenser system and thermometer at one and add 120.0g methyl phenyl ring siloxane and 80.0g dimethicone mixture, 60
oc, vacuum tightness are under-0.095MPa, and constant temperature for some time fully dewaters; Add 4.0g divinyl tetramethyl disiloxane and be roughly equal to the alkali glue of the Tetramethylammonium hydroxide having 50ppm, stir; Under protection of inert gas, be warmed up to 120
oc, balanced reaction 4.0 hours; Be warmed up to 150 again
oc decomposition catalyst, maintains for some time; Be warmed up to 200 further
oc is under the condition of-0.090MPa in vacuum tightness, removes low-boiling-point substance extremely without obvious cut, then room temperature during vacuum cooling.
Detected result: product is transparent, productive rate is higher than 85%, and viscosity is about 750mpa and leads high, and refractive index is 1.491, and volatile matter is lower than 1.0%.
embodiment 3
Be equipped with in the there-necked flask of the 500ml of whipping appts, condenser system and thermometer at one and add 130.0g methyl phenyl ring siloxane and 70.0g octamethylcyclotetrasiloxane, 50
oc, vacuum tightness are under-0.100MPa, and constant temperature for some time fully dewaters; Add 2.5g divinyl tetramethyl disiloxane and be roughly equal to the alkali glue of the Tetramethylammonium hydroxide having 80ppm, stir; Under protection of inert gas, be warmed up to 125
oc, balanced reaction 4.0 hours; Be warmed up to 160 again
oc decomposition catalyst also vacuumizes, and maintains for some time; Be warmed up to 190 further
oc is under the condition of-0.090MPa in vacuum tightness, removes low-boiling-point substance extremely without obvious cut, then room temperature during vacuum cooling.
Detected result: product is transparent, productive rate higher than 89%, viscosity be about 1770mpa higher than, refractive index is 1.500, and volatile matter is lower than 1.0%.
embodiment 4
Be equipped with in the there-necked flask of the 500ml of whipping appts, condenser system and thermometer at one and add 140.0g methyl phenyl ring siloxane and 60.0g t etram-ethyltetravinylcyclotetrasiloxane, 50
oc, vacuum tightness are under-0.095MPa, and constant temperature for some time fully dewaters; Add 4.2g hexamethyldisiloxane and be roughly equal to the alkali glue of the Tetramethylammonium hydroxide having 150ppm, stir.Under protection of inert gas, be warmed up to 130
oc, balanced reaction 3.5 hours; Be warmed up to 160 again
oc decomposition catalyst, maintains for some time; Be warmed up to 200 further
oc is under the condition of-0.100MPa in vacuum tightness, removes low-boiling-point substance extremely without obvious cut, then room temperature during vacuum cooling.
Detected result: product is transparent, productive rate higher than 92%, viscosity be about 1500mpa higher than, refractive index is 1.508, and volatile matter is lower than 1.0%.
embodiment 5
Be equipped with in the there-necked flask of the 500ml of whipping appts, condenser system and thermometer at one and add 100.0g aminomethyl phenyl-dimethicone and 100.0g dimethicone mixture, 60
oc, vacuum tightness are under-0.095MPa, and constant temperature for some time fully dewaters; Add 6.5g divinyl tetramethyl disiloxane and be roughly equal to the alkali glue of the Tetramethylammonium hydroxide having 100ppm, stir; Under protection of inert gas, be warmed up to 130
oc, balanced reaction 3.5 hours; Be warmed up to 160 again
oc decomposition catalyst, maintains for some time; Be warmed up to 190 further
oc is under the condition of-0.095MPa in vacuum tightness, removes low-boiling-point substance extremely without obvious cut, then room temperature during vacuum cooling.
Detected result: product is transparent, productive rate is higher than 90%, and viscosity is about 800mpa and leads high, and refractive index is 1.431, and volatile matter is lower than 1.0%.
embodiment 6
Be equipped with in the there-necked flask of the 500ml of whipping appts, condenser system and thermometer at one and add 120.0g aminomethyl phenyl-dimethicone and 80.0g octamethylcyclotetrasiloxane, 60
oc, vacuum tightness are under-0.095MPa, and constant temperature for some time fully dewaters; Add 10g divinyl tetramethyl disiloxane and be roughly equal to the alkali glue of the trimethyl ammonium hydroxide having 100ppm, stir.Under protection of inert gas, be warmed up to 125
oc, balanced reaction 4.0 hours; Be warmed up to 170 again
oc decomposition catalyst, maintains for some time; Be warmed up to 200 further
oc is under the condition of-0.090MPa in vacuum tightness, removes low-boiling-point substance extremely without obvious cut, then room temperature during vacuum cooling.
Detected result: product is transparent, productive rate is higher than 90%, and viscosity is about 300mpa and leads high, and refractive index is 1.458, and volatile matter is lower than 1.0%.
embodiment 7
Be equipped with in the there-necked flask of the 500ml of whipping appts, condenser system and thermometer at one and add 135.0g aminomethyl phenyl-dimethicone and 65.0g octamethylcyclotetrasiloxane, 65
oc, vacuum tightness are under-0.090MPa, and constant temperature for some time fully dewaters; Add 4.0g divinyl tetramethyl disiloxane and be roughly equal to the alkali glue of the trimethyl ammonium hydroxide having 90ppm, stir; Under protection of inert gas, be warmed up to 125
oc, balanced reaction 4.0 hours; Be warmed up to 170 again
oc decomposition catalyst, maintains for some time; Be warmed up to 190 further
oc is under the condition of-0.090MPa in vacuum tightness, removes low-boiling-point substance extremely without obvious cut, then room temperature during vacuum cooling.
Detected result: product is transparent, productive rate is higher than 90%, and viscosity is about 850mpa and leads high, and refractive index is 1.470, and volatile matter is lower than 1.0%.
embodiment 8
Be equipped with in the there-necked flask of the 500ml of whipping appts, condenser system and thermometer at one and add 180.0g methyl phenyl ring siloxane and 20.0g t etram-ethyltetravinylcyclotetrasiloxane, 65
ounder C, vacuum tightness is under-0.100MPa, and constant temperature for some time fully dewaters; Add 3.5g hexamethyldisiloxane and be roughly equal to the alkali glue of the Tetramethylammonium hydroxide having 100ppm, stir.Under protection of inert gas, be warmed up to 135
oc, balanced reaction 3.5 hours; Be warmed up to 160 again
oc decomposition catalyst, maintains for some time; Be warmed up to 200 further
oc is under the condition of-0.095MPa in vacuum tightness, removes low-boiling-point substance extremely without obvious cut, then room temperature during vacuum cooling.
Detected result: product is transparent, productive rate is higher than 90%, and viscosity is about 4200 mpa in thing, and refractive index is 1.536, and volatile matter is lower than 1.0%.
embodiment 9
Be equipped with in the there-necked flask of the 500ml of whipping appts, condenser system and thermometer at one and add 190.0g methyl phenyl ring siloxane and 10.0g dimethicone mixture, 50
oc, vacuum tightness are under-0.095MPa, and constant temperature for some time fully dewaters; Add 4.4g hexamethyldisiloxane and be roughly equal to the alkali glue of the trimethyl ammonium hydroxide having 100ppm, stir; Under protection of inert gas, be warmed up to 135
oc, balanced reaction 3.5 hours; Be warmed up to 160 again
oc decomposition catalyst, maintains for some time; Be warmed up to 210 further
oc is under the condition of-0.095MPa in vacuum tightness, removes low-boiling-point substance extremely without obvious cut, then room temperature during vacuum cooling.
Detected result: product is transparent, productive rate higher than 90%, viscosity be about 3800mpa higher than, refractive index is 1.540, and volatile matter is lower than 1.0%.
embodiment 10
Be equipped with in the there-necked flask of the 500ml of whipping appts, condenser system and thermometer at one and add 200.0g methyl phenyl ring siloxane, 70
oc and vacuum tightness are under the condition of-0.095MPa, and constant temperature for some time fully dewaters; Add 4.0g divinyl tetramethyl disiloxane and be roughly equal to the alkali glue of the Tetramethylammonium hydroxide having 150ppm, stir; Under protection of inert gas, be warmed up to 140
oc, balanced reaction 3.0 hours; Be warmed up to 170 again
oc decomposition catalyst, maintains for some time; Be warmed up to 205 further
oc is under the condition of-0.100MPa in vacuum tightness, removes low-boiling-point substance extremely without obvious cut, then room temperature during vacuum cooling.
Detected result: product is transparent, productive rate higher than 90%, viscosity be about 4900mpa higher than, refractive index is 1.546, and volatile matter is lower than 1.0%.
Claims (3)
1. a preparation method for the phenyl-vinyl silicon oil that refractive index is controlled, is characterized in that, comprises the following steps:
(1) under protection of inert gas, by the monomer of 100 weight parts, the end-capping reagent of 0.5 ~ 5.0 weight part, the catalyst mix of 0.5-1.5 weight part evenly after, 100 ~ 140
oring-opening polymerization 3.0 ~ 5.0 hours under C; Described monomer is the cyclosiloxane monomer containing phenyl, or the mix monomer for being made up of according to any proportioning with the cyclosiloxane monomer containing phenyl methyl cyclosiloxane monomer; Described end-capping reagent is selected from divinyl tetramethyl disiloxane, Vinyldimethylethoxysilane, hexamethyldisiloxane or dimethylvinylmethoxysiiane; Described catalyzer is selected from five water Tetramethylammonium hydroxide, tetramethyl ammonium hydroxide solution, trimethyl ammonium hydroxide, Tetramethylammonium hydroxide alkali glue, trimethyl ammonium hydroxide alkali glue;
(2) by the product after step (1) ring-opening polymerization 150 ~ 170
odecomposition catalyst 1-2h under the condition of C, protection of inert gas;
(3) product after step (2) being processed is 190 ~ 210
oc, vacuum tightness are under the condition of-0.09 ~-0.10MPa, remove low-boiling-point substance, until flow out without cut; By removing after the product after low-boiling-point substance is cooled to room temperature, obtain the phenyl-vinyl silicon oil that refractive index is controlled.
2. the preparation method of the phenyl-vinyl silicon oil that a kind of refractive index according to claim 1 is controlled, it is characterized in that, the described cyclosiloxane monomer containing phenyl comprises aminomethyl phenyl cyclotrisiloxane, aminomethyl phenyl cyclotetrasiloxane, aminomethyl phenyl D5, aminomethyl phenyl-dimethicone; Described methyl cyclosiloxane monomer comprises hexamethyl cyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentaandoxane, ten diformazan basic ring six siloxanes, t etram-ethyltetravinylcyclotetrasiloxane.
3. the preparation method of the phenyl-vinyl silicon oil that a kind of refractive index according to claim 1 is controlled, is characterized in that, described monomer obtains through dehydration pre-treatment, and pretreated temperature of dewatering is 50-70
oc, vacuum tightness is 0.09 ~ 0.10MPa.
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| CN104892941A (en) * | 2015-05-26 | 2015-09-09 | 中国工程物理研究院化工材料研究所 | Synthesis process of viscosified phenyl silicone oil for high-power light-emitting diode (LED) packaging |
| CN104892943A (en) * | 2015-06-10 | 2015-09-09 | 杭州福斯特光伏材料股份有限公司 | High-refraction-index phenyl vinyl silicone oil and preparation method thereof |
| CN105037731A (en) * | 2015-08-28 | 2015-11-11 | 上海爱世博有机硅材料有限公司 | Solvent-free vinyl phenyl polysiloxane and preparation method thereof |
| CN105295051A (en) * | 2015-11-25 | 2016-02-03 | 广州旭川合成材料有限公司 | Methyl vinyl phenyl silicone oil, preparation method and applications thereof |
| CN105524279A (en) * | 2015-11-26 | 2016-04-27 | 杭州师范大学 | Preparation method for heat-conducting methylphenyl silicone oil |
| CN105754104A (en) * | 2016-05-18 | 2016-07-13 | 上海化工研究院 | Preparation method of methyl phenyl vinyl silicone oil with controllable refractive index |
| CN106478951A (en) * | 2016-10-18 | 2017-03-08 | 华南理工大学 | A kind of preparation method of LED packaging plastic methyl and phenyl hydrogen-containing silicon oil |
| CN108239285A (en) * | 2018-01-25 | 2018-07-03 | 广东优聚实业有限公司 | A kind of low phenyl-vinyl silicon oil and preparation method thereof |
| CN109400881A (en) * | 2018-10-22 | 2019-03-01 | 浙江衢州正邦有机硅有限公司 | A kind of preparation method of methyl phenyl silicone rubber |
| CN109678356A (en) * | 2019-01-11 | 2019-04-26 | 湖北新四海化工股份有限公司 | A kind of high light transmission glass hydrophobing agent and preparation method thereof |
| CN110229337A (en) * | 2019-07-11 | 2019-09-13 | 枣阳市华威硅氟材料有限公司 | The production method of phenyl methyl silicone oil |
| CN111560119A (en) * | 2020-07-09 | 2020-08-21 | 威海新元化工有限公司 | Preparation method of dimethyl diphenyl polysiloxane |
| CN113321810A (en) * | 2021-06-01 | 2021-08-31 | 万华化学集团股份有限公司 | Q-type high-refraction phenyl vinyl silicone oil, and synthesis method and application thereof |
| CN113698605A (en) * | 2021-09-27 | 2021-11-26 | 矽时代材料科技股份有限公司 | Preparation method of high-purity polysiloxane |
| CN114058290A (en) * | 2021-11-18 | 2022-02-18 | 四川富彩科技有限公司 | Solvent-free organic silicon release agent with ultralow release force and preparation method thereof |
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| CN104892941A (en) * | 2015-05-26 | 2015-09-09 | 中国工程物理研究院化工材料研究所 | Synthesis process of viscosified phenyl silicone oil for high-power light-emitting diode (LED) packaging |
| CN104892943A (en) * | 2015-06-10 | 2015-09-09 | 杭州福斯特光伏材料股份有限公司 | High-refraction-index phenyl vinyl silicone oil and preparation method thereof |
| CN105037731A (en) * | 2015-08-28 | 2015-11-11 | 上海爱世博有机硅材料有限公司 | Solvent-free vinyl phenyl polysiloxane and preparation method thereof |
| CN105295051A (en) * | 2015-11-25 | 2016-02-03 | 广州旭川合成材料有限公司 | Methyl vinyl phenyl silicone oil, preparation method and applications thereof |
| CN105524279A (en) * | 2015-11-26 | 2016-04-27 | 杭州师范大学 | Preparation method for heat-conducting methylphenyl silicone oil |
| CN105524279B (en) * | 2015-11-26 | 2018-05-01 | 杭州师范大学 | A kind of preparation method of aminomethyl phenyl heat conduction silicone oil |
| CN105754104A (en) * | 2016-05-18 | 2016-07-13 | 上海化工研究院 | Preparation method of methyl phenyl vinyl silicone oil with controllable refractive index |
| CN106478951A (en) * | 2016-10-18 | 2017-03-08 | 华南理工大学 | A kind of preparation method of LED packaging plastic methyl and phenyl hydrogen-containing silicon oil |
| CN108239285A (en) * | 2018-01-25 | 2018-07-03 | 广东优聚实业有限公司 | A kind of low phenyl-vinyl silicon oil and preparation method thereof |
| CN109400881A (en) * | 2018-10-22 | 2019-03-01 | 浙江衢州正邦有机硅有限公司 | A kind of preparation method of methyl phenyl silicone rubber |
| CN109678356A (en) * | 2019-01-11 | 2019-04-26 | 湖北新四海化工股份有限公司 | A kind of high light transmission glass hydrophobing agent and preparation method thereof |
| CN109678356B (en) * | 2019-01-11 | 2021-11-23 | 湖北新四海化工股份有限公司 | High-light-transmittance glass hydrophobing agent and preparation method thereof |
| CN110229337A (en) * | 2019-07-11 | 2019-09-13 | 枣阳市华威硅氟材料有限公司 | The production method of phenyl methyl silicone oil |
| CN111560119A (en) * | 2020-07-09 | 2020-08-21 | 威海新元化工有限公司 | Preparation method of dimethyl diphenyl polysiloxane |
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Application publication date: 20150311 |