CN106496561A - A kind of equally distributed methyl phenyl silicone rubber preparation method of phenyl - Google Patents
A kind of equally distributed methyl phenyl silicone rubber preparation method of phenyl Download PDFInfo
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- CN106496561A CN106496561A CN201610835367.4A CN201610835367A CN106496561A CN 106496561 A CN106496561 A CN 106496561A CN 201610835367 A CN201610835367 A CN 201610835367A CN 106496561 A CN106496561 A CN 106496561A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
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Abstract
A kind of equally distributed methyl phenyl silicone rubber preparation method of phenyl, it is related to a kind of method for preparing rubber, the invention discloses equally distributed methyl phenyl silicone rubber of a kind of phenyl and preparation method thereof, by dimethyldichlorosilane and dichloromethyl phenylsilane, there is cohydrolysis reaction under hydrochloric acid effect, adding a certain amount of LiOH powder makes its catalytic pyrolysis, obtains pure containing Me2The cyclic methyl phenylpolysiloxane of SiO chain links so as to octamethylcy-clotetrasiloxane, t etram-ethyltetravinylcyclotetrasiloxane under the effect of catalyst TMAH, the methyl phenyl silicone rubber that different molecular quality is prepared for using anionic polymerization.Dimethyl silica chain link in product of the present invention is equally distributed with aminomethyl phenyl silica chain link, there is no the difference of refractive index, and in the case of identical phenyl content, the common phenyl siloxane rubber of its ratio of viscosities is low, and heat resisting temperature is higher, mechanical property is more preferable.
Description
Technical field
The present invention relates to a kind of method for preparing rubber, the equally distributed methyl phenyl silicone rubber of more particularly to a kind of phenyl
Preparation method.
Background technology
Methyl phenyl silicone rubber refers to that a part of silicon atom on main chain is connected with dimethyl and another part is connected with a first
Base and the silicon rubber of a phenyl, special chemical constitution give a series of its excellent properties, are widely used to high temperature resistant painting
The every field such as layer, heat-conducting glue, electronic apparatus, industry light industry textile industry, building materials.With the continuous expansion of its application, tradition meaning
Phenyl siloxane rubber in justice cannot meet day by day harsh use requirement, and its basic reason is that phenyl ring is not on main chain
It is uniformly distributed.
Current methyl phenyl vinyl silicone rubber is by tetramethyl tetraphenyl cyclotetrasiloxane and prestox ring four
Siloxanes carries out copolymerization and obtains, and in product, dimethyl silica chain link uniformly can not be alternately distributed with aminomethyl phenyl silica chain link,
Therefore the refractive index of different segments on strand is different, so as to obtain the phenyl silicone oil of homogeneous transparent, excellent performance.
Shown in its structure is generally as follows：
.
Content of the invention
It is an object of the invention to provide a kind of equally distributed methyl phenyl silicone rubber preparation method of phenyl, this method will
, under hydrochloric acid effect, there is cohydrolysis reaction, the dimethyl-silicon in product in dimethyldichlorosilane and dichloromethyl phenylsilane
Oxygen chain link is equally distributed with aminomethyl phenyl silica chain link, there is no the difference of refractive index, in the case of identical phenyl content,
The common phenyl siloxane rubber of its ratio of viscosities is low, and heat resisting temperature is higher, mechanical property is more preferable.
The purpose of the present invention is achieved through the following technical solutions：
A kind of equally distributed methyl phenyl silicone rubber preparation method of phenyl, methods described include following synthesis step：
（1）Processed：In the 250ml there-necked flasks for being furnished with agitator, thermocouple, TMAH methyl alcohol is put into
Solution, the moisture and methyl alcohol about 1h under conditions of 35 ~ 45 DEG C of vacuum distillation in removing system；
（2）Ring-opening polymerization：Closure agent and cyclosiloxane is added, 110 DEG C is warming up to, 4 ~ 5 h of polymerisation；
（3）Decomposition catalyst：There-necked flask is warming up to 170 DEG C of decomposition catalyst about 1h, is needed always to three mouthfuls during being somebody's turn to do
Flask is passed through N2To go out catalyst decomposition products completely；
（4）Removing low-boiling-point substance：Finally, above-mentioned system is transferred in cucurbit, low boiling is fully removed under 200 DEG C of vacuum environments
Thing, is cooled to the product that room temperature obtains clear.
A kind of equally distributed methyl phenyl silicone rubber preparation method of described phenyl, described TMAH first
Alcoholic solution addition is the 0.01 ~ 1% of ring body mass content to be added.
A kind of equally distributed methyl phenyl silicone rubber preparation method of described phenyl, described closure agent are divinyl
One kind in tetramethyl disiloxane, diphenyltetramethyl disiloxane, HMDO, distilled water, addition are to treat
Plus the 0.01 ~ 10% of ring body mass content.
A kind of equally distributed methyl phenyl silicone rubber preparation method of described phenyl, described cyclosiloxane be containing
Me2In the cyclic methyl phenylpolysiloxane of SiO chain links and octamethylcy-clotetrasiloxane, t etram-ethyltetravinylcyclotetrasiloxane
One or more.
Advantages of the present invention with effect is：
Methyl phenyl silicone rubber in the present invention is by containing Me2The cyclic methyl phenylpolysiloxane of SiO chain links and prestox ring
Tetrasiloxane copolymerization and obtain, the dimethyl silica chain link in product is equally distributed with aminomethyl phenyl silica chain link, does not exist
The difference of refractive index, in the case of identical phenyl content, the common phenyl siloxane rubber of its ratio of viscosities is low, and heat resisting temperature higher,
Mechanical property is more preferable.The product that different phenyl contents can be obtained by the proportioning for controlling two kinds of ring bodies, by adjusting closure agent
Addition can obtain the different product of molecular weight, to adapt to different use conditions.Its backbone structure is as follows：
.
Specific embodiment
With reference to embodiment, the present invention is described in detail.
The equally distributed methyl phenyl silicone rubber of phenyl, its synthetic method are as follows：
（1）Processed：In the 250ml there-necked flasks for being furnished with agitator, thermocouple, certain mass tetramethyl hydrogen-oxygen is put into
Change ammonium methanol solution, the moisture and methyl alcohol about 1h under conditions of 35 ~ 45 DEG C of vacuum distillation in removing system.
（2）Ring-opening polymerization：Appropriate cyclosiloxane is added, 110 DEG C is warming up to, 4 ~ 5 h of polymerisation.
（3）Decomposition catalyst：There-necked flask is warming up to 170 DEG C of decomposition catalyst about 1h, should during need always to
There-necked flask is passed through N2To go out catalyst decomposition products completely.
（4）Removing low-boiling-point substance：Finally, above-mentioned system is transferred in cucurbit, is fully removed under 200 DEG C of vacuum environments
Low-boiling-point substance, is cooled to the product that room temperature obtains clear.
Above-mentioned TMAH methanol solution addition is the 0.01 ~ 1% of ring body mass content to be added.
Above-mentioned closure agent is divinyl tetramethyl disiloxane, diphenyltetramethyl disiloxane, two silicon of hexamethyl
One kind in oxygen alkane, distilled water, addition are the 0.01 ~ 10% of ring body mass content to be added.
Above-mentioned cyclosiloxane is containing Me2The cyclic methyl phenylpolysiloxane of SiO chain links and octamethylcy-clotetrasiloxane,
One or more in t etram-ethyltetravinylcyclotetrasiloxane.
The above-mentioned cyclic methyl phenylpolysiloxane synthesis step containing Me2SiO chain links is as follows：
（1）By the dimethyldichlorosilane and dichloromethyl phenylsilane of different mol ratio, 6mol/L hydrochloric acid and toluene (plus
Enter amount 1 times of cyclotetrasiloxane molal quantity is generated according in theory 100%) under effect, there is cohydrolysis reaction, wherein in hydrochloric acid
Water is 10 with the mol ratio of mix monomer:1.The reaction obtains three ring bodies with phenyl, four ring bodies, five ring body annular siloxanes
The siloxanes mixing liquid of the straight-chain not waited with molecular weight.
（2）Liquid after by hydrolysis after stratification takes upper strata oily liquids and removes for 60-70 DEG C in a rotary evaporator
Water and toluene, after three hours are put into remaining liq in reactor, add the LiOH powder of institute tapping body mass ratio 1.5% to make
Its catalytic pyrolysis, control programming rate are gradually heating to 250 DEG C on the premise of ensureing not slug, after 250 DEG C of cracking one hour
300 DEG C are warming up to again till flowing out without liquid.It is in receiving flask pure containing Me2The cyclomethicones of SiO chain links
Phenyl siloxane, structure are DnDPh m(D=Me2SiO;DPh=MePhSiO) (n=1,2,3;m=1,2,3;3《n+m《6 ).
Embodiment 1
（1）Me by 95.6mL2SiCl2MePhSiCl with 32.1mL2（Mol ratio is 4:1）, in the hydrochloric acid of 6mol/L and certain
Under amount toluene effect, there is cohydrolysis reaction, water is 10 with the mol ratio of mix monomer wherein in hydrochloric acid:1.The reaction obtains band
There is the siloxanes mixing liquid of three ring bodies, four ring bodies, five ring body annular siloxanes and the molecular weight of phenyl straight-chain not etc..
（2）Liquid after by hydrolysis after stratification takes upper strata oily liquids and removes for 60-70 DEG C in a rotary evaporator
Under water and toluene (addition is according in theory 100% generate cyclotetrasiloxane molal quantity 1 times) effect, will be surplus after three hours
Extraction raffinate body is put in reactor, is added the LiOH powder of institute tapping body mass ratio 1.5% to make its catalytic pyrolysis, is controlled programming rate
250 DEG C are gradually heating on the premise of ensureing not slug, after cracking one hour at 250 DEG C, 300 DEG C are warming up to again until without liquid
Till body flows out.It is in receiving flask pure containing Me2The cyclic methyl phenylpolysiloxane of SiO chain links, structure are DnDP m(D
=Me2SiO;DP=MePhSiO, n=1,2,3;m=1,2,3;3《n+m《6, Ph/Si=1:5).
（3）Processed：In the 250ml there-necked flasks for being furnished with agitator, thermocouple, put into ring body quality to be added and contain
The TMAH methanol solution of amount 0.08%, the moisture in removing system and first under conditions of 35 ~ 45 DEG C of vacuum distillation
Alcohol about 1h.
（4）Ring-opening polymerization：After adding the closure agent divinyl tetramethyl disiloxane of different ring body total mass ratios
23g octamethylcy-clotetrasiloxanes, cyclic methyl phenylpolysiloxanes of the 27g containing Me2SiO chain links is added to be warming up to 110 DEG C, gather
Close 4 ~ 5 h of reaction.
（5）Decomposition catalyst：There-necked flask is warming up to 170 DEG C of decomposition catalyst about 1h, should during need always to
There-necked flask is passed through N2To go out catalyst decomposition products completely.
（6）Removing low-boiling-point substance：Finally, above-mentioned system is transferred in cucurbit, is fully removed under 200 DEG C of vacuum environments
Low-boiling-point substance, is cooled to the ethenyl blocking methyl phenyl silicone rubber (Ph/Si=1 that room temperature obtains different molecular weight clear:
10).After solidification, its performance is as shown in the table：
.
Embodiment 2
（1）Me by 95.6mL2SiCl2MePhSiCl with 32.1mL2（Mol ratio is 4:1）, in the hydrochloric acid of 6mol/L and certain
Under amount toluene effect, there is cohydrolysis reaction, water is 10 with the mol ratio of mix monomer wherein in hydrochloric acid:1.The reaction obtains band
There is the siloxanes mixing liquid of three ring bodies, four ring bodies, five ring body annular siloxanes and the molecular weight of phenyl straight-chain not etc..
（2）Liquid after by hydrolysis after stratification takes upper strata oily liquids and removes for 60-70 DEG C in a rotary evaporator
Under water and toluene (addition is according in theory 100% generate cyclotetrasiloxane molal quantity 1 times) effect, will be surplus after three hours
Extraction raffinate body is put in reactor, is added the LiOH powder of institute tapping body mass ratio 1.5% to make its catalytic pyrolysis, is controlled programming rate
250 DEG C are gradually heating on the premise of ensureing not slug, after cracking one hour at 250 DEG C, 300 DEG C are warming up to again until without liquid
Till body flows out.It is in receiving flask pure containing Me2The cyclic methyl phenylpolysiloxane of SiO chain links, structure are DnDP m(D
=Me2SiO;DP=MePhSiO, n=1,2,3;m=1,2,3;3《n+m《6, Ph/Si=1:5).
（3）Processed：In the 250ml there-necked flasks for being furnished with agitator, thermocouple, put into ring body quality to be added and contain
The TMAH methanol solution of amount 0.08%, the moisture in removing system and first under conditions of 35 ~ 45 DEG C of vacuum distillation
Alcohol about 1h.
（4）Ring-opening polymerization：Different quality is added after adding the closure agent HMDO of 0.1% total mass ratio
Octamethylcy-clotetrasiloxane, 27g containing Me2SiO chain links cyclic methyl phenylpolysiloxane, 0.3g tetramethyl tetravinyl rings
Tetrasiloxane, is warming up to 110 DEG C, 4 ~ 5 h of polymerisation.
（5）Decomposition catalyst：There-necked flask is warming up to 170 DEG C of decomposition catalyst about 1h, should during need always to
There-necked flask is passed through N2To go out catalyst decomposition products completely.
（6）Removing low-boiling-point substance：Finally, above-mentioned system is transferred in cucurbit, is fully removed under 200 DEG C of vacuum environments
Low-boiling-point substance, is cooled to the high temperature vulcanized glue methyl phenyl vinyl silicone rubber that room temperature obtains the clear of different phenyl contents
(Ph/Si≈1:10).After solidification, its performance is as shown in the table：
Can to sum up obtain, the different product of molecular weight can be obtained with the addition for overregulating double-seal head agent, and different quality ratio
Octamethylcy-clotetrasiloxane, the cyclic methyl phenylpolysiloxane containing Me2SiO chain links, t etram-ethyltetravinylcyclotetrasiloxane
The product of different phenyl, contents of ethylene is obtained, and formula specifically can be adjusted according to physical condition.
Above-mentioned specific embodiment is exemplary, be in order to preferably make skilled artisans appreciate that this
Invention, it is impossible to be not understood as the restriction for including scope to the present invention；As long as according to disclosed spirit made appoint
How with change or modification, scope by the invention is each fallen within.
Claims (4)
1. the equally distributed methyl phenyl silicone rubber preparation method of a kind of phenyl, it is characterised in that methods described includes following conjunction
Into step：
（1）Processed：In the 250ml there-necked flasks for being furnished with agitator, thermocouple, TMAH methyl alcohol is put into
Solution, the moisture and methyl alcohol about 1h under conditions of 35 ~ 45 DEG C of vacuum distillation in removing system；
（2）Ring-opening polymerization：Closure agent and cyclosiloxane is added, 110 DEG C is warming up to, 4 ~ 5 h of polymerisation；
（3）Decomposition catalyst：There-necked flask is warming up to 170 DEG C of decomposition catalyst about 1h, is needed always to three mouthfuls during being somebody's turn to do
Flask is passed through N2To go out catalyst decomposition products completely；
（4）Removing low-boiling-point substance：Finally, above-mentioned system is transferred in cucurbit, low boiling is fully removed under 200 DEG C of vacuum environments
Thing, is cooled to the product that room temperature obtains clear.
2. the equally distributed methyl phenyl silicone rubber preparation method of a kind of phenyl according to claim 1, it is characterised in that
Described TMAH methanol solution addition is the 0.01 ~ 1% of ring body mass content to be added.
3. the equally distributed methyl phenyl silicone rubber preparation method of a kind of phenyl according to claim 1, it is characterised in that
Described closure agent is divinyl tetramethyl disiloxane, diphenyltetramethyl disiloxane, HMDO, distillation
One kind in water, addition are the 0.01 ~ 10% of ring body mass content to be added.
4. the equally distributed methyl phenyl silicone rubber preparation method of a kind of phenyl according to claim 1, it is characterised in that
Described cyclosiloxane is containing Me2The cyclic methyl phenylpolysiloxane of SiO chain links and octamethylcy-clotetrasiloxane, tetramethyl four
One or more in vinyl cyclotetrasiloxane.
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| CN201610835367.4A CN106496561A (en) | 2016-09-21 | 2016-09-21 | A kind of equally distributed methyl phenyl silicone rubber preparation method of phenyl |
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| CN201610835367.4A CN106496561A (en) | 2016-09-21 | 2016-09-21 | A kind of equally distributed methyl phenyl silicone rubber preparation method of phenyl |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108976422A (en) * | 2018-06-15 | 2018-12-11 | 北京石油化工学院 | A kind of high viscosity bumper and absorbing shock phenyl siloxane rubber 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 |
| CN109722033A (en) * | 2018-12-10 | 2019-05-07 | 沈阳化工大学 | A kind of two anthryl diphenyl ether vinylsiloxane rubber preparation methods |
| CN110358089A (en) * | 2018-04-11 | 2019-10-22 | 苏州润特新材料科技有限公司 | A kind of preparation method of alkylaryl modified silicon oil |
| CN111518132A (en) * | 2020-06-01 | 2020-08-11 | 上海树脂厂有限公司 | Preparation method of methyl phenyl mixed ring body and preparation method of methyl phenyl silicone rubber |
| CN113636890A (en) * | 2021-09-18 | 2021-11-12 | 成都正光投资集团有限公司 | Selenium-rich slow-release cadmium inhibitor and preparation method thereof |
| CN116804086A (en) * | 2023-08-25 | 2023-09-26 | 成都思立可科技有限公司 | Long-chain alkyl-polar group co-modified polysiloxane and preparation method thereof |
-
2016
- 2016-09-21 CN CN201610835367.4A patent/CN106496561A/en not_active Withdrawn
Non-Patent Citations (1)
| Title |
|---|
| 来国桥: ""1000t/a甲基苯基二氯硅烷及含MePhSiO链节的新型聚硅氧烷"", 《2006年第十三届中国有机硅学术交流会论文集》 * |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110358089A (en) * | 2018-04-11 | 2019-10-22 | 苏州润特新材料科技有限公司 | A kind of preparation method of alkylaryl modified silicon oil |
| CN108976422A (en) * | 2018-06-15 | 2018-12-11 | 北京石油化工学院 | A kind of high viscosity bumper and absorbing shock phenyl siloxane rubber and preparation method thereof |
| CN108976422B (en) * | 2018-06-15 | 2021-03-16 | 北京石油化工学院 | High-viscosity buffering and damping phenyl silicone rubber 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 |
| CN109722033A (en) * | 2018-12-10 | 2019-05-07 | 沈阳化工大学 | A kind of two anthryl diphenyl ether vinylsiloxane rubber preparation methods |
| CN109722033B (en) * | 2018-12-10 | 2021-08-06 | 沈阳化工大学 | Preparation method of dianthranyl diphenyl ether vinyl silicone rubber |
| CN111518132A (en) * | 2020-06-01 | 2020-08-11 | 上海树脂厂有限公司 | Preparation method of methyl phenyl mixed ring body and preparation method of methyl phenyl silicone rubber |
| CN111518132B (en) * | 2020-06-01 | 2023-09-26 | 上海树脂厂有限公司 | Preparation method of methylphenyl mixed ring body and preparation method of methylphenyl silicon rubber |
| CN113636890A (en) * | 2021-09-18 | 2021-11-12 | 成都正光投资集团有限公司 | Selenium-rich slow-release cadmium inhibitor and preparation method thereof |
| CN113636890B (en) * | 2021-09-18 | 2022-04-15 | 成都正光投资集团有限公司 | Selenium-rich slow-release cadmium inhibitor and preparation method thereof |
| CN116804086A (en) * | 2023-08-25 | 2023-09-26 | 成都思立可科技有限公司 | Long-chain alkyl-polar group co-modified polysiloxane and preparation method thereof |
| CN116804086B (en) * | 2023-08-25 | 2023-11-07 | 成都思立可科技有限公司 | Long-chain alkyl-polar group co-modified polysiloxane and preparation method thereof |
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