CN105111446B - A kind of fluorine-containing phenyl hydrogen-containing silicon oil crosslinking agent and preparation method thereof - Google Patents
A kind of fluorine-containing phenyl hydrogen-containing silicon oil crosslinking agent and preparation method thereof Download PDFInfo
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- CN105111446B CN105111446B CN201510595014.7A CN201510595014A CN105111446B CN 105111446 B CN105111446 B CN 105111446B CN 201510595014 A CN201510595014 A CN 201510595014A CN 105111446 B CN105111446 B CN 105111446B
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Abstract
The invention belongs to the technical field of crosslinking agent, a kind of fluorine-containing phenyl hydrogen-containing silicon oil crosslinking agent and preparation method thereof is disclosed.Methods described mixes to add base catalyst into low viscosity methyl-silicone oil, phenyl ring siloxane and fluorosilicon oil, heats up and constant temperature stirring, cooling, sequentially adds acid catalyst and containing hydrogen silicone oil, balanced reaction, subsequent treatment is carried out after having reacted, the fluorine-containing phenyl hydrogen-containing silicon oil crosslinking agent of water white transparency is obtained.Methyl cyclosiloxane and end-capping reagent need not be added in the preparation method of the present invention, technique is simplified, improves product quality and stability；The raw material used is not chloride and alkoxy, it is to avoid the introducing of chlorion and the residual of alkoxy；The present invention does not use any solvent, human body will not be damaged, also environment will not be polluted；Crosslinking agent high income prepared by the present invention.
Description
Technical field
The invention belongs to the technical field of crosslinking agent, it is related to a kind of fluorine-containing phenyl hydrogen-containing silicon oil crosslinking agent, and in particular to one
Plant fluorine-containing phenyl hydrogen-containing silicon oil crosslinking agent and preparation method thereof.The fluorine-containing phenyl hydrogen-containing silicon oil crosslinking agent specifically refers to one kind and contained
There is fluorine-based and phenyl comodified containing hydrogen silicone oil crosslinking agent.
Background technology
Phenyl siloxane rubber is one of principal item of silicon rubber, wide with good resistant of high or low temperature, radiation resistance etc.
It is general to be applied to the fields such as electronics, machinery, Aero-Space.Low-phenyl silicone rubber lower temperature resistance is significantly, also flexible at -110 DEG C；
High phenyl siloxane rubber can be in 350 DEG C of long-term uses；Under gamma-rays irradiation, phenyl siloxane rubber has excellent radiation resistance.
But phenyl siloxane rubber oil resistant solvent resistance is not good, its use under oil medium, solvent environment is limited.
Fluorosioloxane rubber has the weatherability of brilliance, chemistry steady because combining the double properties of silicon rubber and fluorocarbons
Qualitative and water and oil-resistant, available for aircraft and automotive oil tank sealing, oil resistant pad, O-ring, oil pipe etc..Fluorosioloxane rubber has
Excellent oil resistant solvent resistance, but its high temperature resistant low performance is limited, and slow oxidative degradation will occur at 200 DEG C, produces HF
Gas.
Fluorine-containing phenyl siloxane rubber is fluorine-based and phenyl comodified silicon rubber, has had the spy of fluorosioloxane rubber and phenyl siloxane rubber concurrently
Point, compensate for respective deficiency, with excellent resistant of high or low temperature, radiation resistance, oil resistant, solvent resistance etc..
Fluorine-containing phenyl hydrogen-containing silicon oil as the fluorine-containing phenyl siloxane rubber of add-on type reliable crosslinking agent, to fluorine-containing phenyl siloxane rubber
Performance play decisive role.
The preparation of fluorine-containing phenyl hydrogen-containing silicon oil can use with fluorine-containing cyclosiloxane, phenyl ring siloxane, methyl cyclosiloxane,
Containing hydrogen silicone oil, end-capping reagent etc. are raw material, through acid catalyzed polymerisation, neutralization, take off low technique, synthesize fluorine-containing phenyl hydrogen-containing silicon oil.This
Process can not use base catalyst, be easily caused containing hydrogen silicone oil and fall hydrogen crosslinking, and because phenyl ring siloxane is solid, it is and fluorine-containing
Cyclosiloxane, methyl cyclosiloxane, containing hydrogen silicone oil are immiscible, and phenyl ring siloxane ring body stress is big, under acid condition very
Difficult open loop is thorough, even if the extension reaction time, it is also difficult to obtain fully transparent product.
The content of the invention
In order to overcome the shortcoming and defect of prior art, it is an object of the invention to provide a kind of technique is simple, quality is steady
The preparation method of fixed fluorine-containing phenyl hydrogen-containing silicon oil crosslinking agent.The present invention is using low viscosity methyl-silicone oil as raw material, elder generation and benzyl ring
Siloxanes, fluorosilicon oil carry out ring-opening polymerisation in the basic conditions, phenyl ring siloxane is liquefied, and form clear homogeneous system, so
Afterwards in acid condition, containing hydrogen silicone oil is added, molecule aggregation rearrangement is carried out, finally neutralized, vacuum filtration obtains product, during
Without addition methyl cyclosiloxane and end-capping reagent in addition, it is to avoid need high temperature removal to have neither part nor lot in the methyl ring silicon of reaction after reaction
The low molecules such as oxygen alkane, simplify technique, improve product quality and stability.
Another object of the present invention is to provide the fluorine-containing phenyl hydrogen-containing silicon oil crosslinking prepared by above-mentioned preparation method
Agent.
The purpose of the present invention is achieved by following technical proposals：
A kind of preparation method of fluorine-containing phenyl hydrogen-containing silicon oil crosslinking agent, specifically includes following steps：
Base catalyst is added into low viscosity methyl-silicone oil, phenyl ring siloxane and fluorosilicon oil, is mixed, heats up and constant temperature is stirred
Mix, cool down, sequentially add acid catalyst and containing hydrogen silicone oil, balanced reaction carries out subsequent treatment after having reacted, obtains water white transparency
Fluorine-containing phenyl hydrogen-containing silicon oil crosslinking agent.
In low viscosity methyl-silicone oil, phenyl ring siloxane, fluorosilicon oil and containing hydrogen silicone oil, the low viscosity methyl-silicone oil
Mass percent be that the mass percent of 10~80%, phenyl ring siloxane is the mass percent of 15~50%, fluorosilicon oil：
5~40%, the quality of the containing hydrogen silicone oil is low viscosity methyl-silicone oil, phenyl ring siloxane and fluorosilicon oil gross mass 20~
100%.
The heating refers to be warming up to 150~180 DEG C, and the time of the constant temperature stirring is 5~8h, and the mixing speed is
80~200 revs/min；The balanced reaction time is 4~6h, and the temperature of the balanced reaction is room temperature；The temperature of the cooling
For room temperature.
The subsequent treatment refers to after balanced reaction to neutralize reaction solution using nertralizer, then is filtered by vacuum.
The nertralizer consumption is 2~4 times of acid catalyst quality, and the neutralization time is 1~2h；Described nertralizer is sodium carbonate
Or sodium acid carbonate.
Described low viscosity methyl-silicone oil is the dimethyl silicone polymer (molecular weight is 800~4000) of methyl blocking, is glued
Spend for 5~50mPa.s (25 DEG C)；Under base catalyst effect, molecular backbone occur fracture and with phenyl siloxane chain link, fluorine-containing
Siloxane unit is reset, and forms what is be evenly distributed, simultaneously containing methylsiloxane chain link, phenyl siloxane chain link, fluorine-containing silica
The molecular structure of alkane chain link, meanwhile, viscosity or molecular weight of the end-capping reagent also to polymerizate contained by methyl-silicone oil itself have
Limitation.
Described phenyl ring siloxane is one kind in octaphenylcyclotetrasiloxane or tetramethyl tetraphenyl cyclotetrasiloxane
Or two kinds.
Described fluorosilicon oil is dimethyl silicone polymer (the Guangzhou hard iron Thailand containing trifluoropropyl group of hydroxyl or methyl blocking
Organosilicon material Co., Ltd, model：F-200, molecular weight 1000~6000), viscosity is 5~100mPa.s (25 DEG C).
Described containing hydrogen silicone oil is dimethyl silicone polymer (Japanese SHIN-ETSU HANTOTAI's organosilicon international trade (Shanghai) containing hydrogen-based
Co., Ltd, model：KF-99, molecular weight 4000~6000), hydrogen content 0.1~1.6%.
Described base catalyst is lithium hydroxide, potassium hydroxide or cesium hydroxide.The consumption of the base catalyst is low viscous
Spend the 0.05~0.1% of methyl-silicone oil, phenyl ring siloxane and fluorosilicon oil gross mass.
Described acid catalyst is the concentrated sulfuric acid, trifluoromethanesulfonic acid, p-methyl benzenesulfonic acid, the preferably concentrated sulfuric acid.The acid catalysis
The consumption of agent is the 2~5% of low viscosity methyl-silicone oil, phenyl ring siloxane, fluorosilicon oil and containing hydrogen silicone oil gross mass.
The fluorine-containing phenyl hydrogen-containing silicon oil crosslinking agent is prepared by above-mentioned preparation method.
The present invention compared with prior art, with following beneficial effect：
(1) fluorine-containing phenyl hydrogen-containing silicon oil of the invention need not add methyl cyclosiloxane and envelope in addition during preparation
Hold agent, it is to avoid need high temperature removal to have neither part nor lot in the low molecules such as the methyl cyclosiloxane of reaction after reaction, simplify technique, improve
Product quality and stability；
(2) fluorine-containing phenyl hydrogen-containing silicon oil of the invention, the raw material used is not chloride and alkoxy, it is to avoid hydrolysis produces big
The hydrochloric acid and alcohol of amount, are prevented effectively from the introducing of chlorion and the residual of alkoxy；
(3) present invention does not use any solvent, human body will not be damaged, also environment will not be polluted；
(4) methyl-silicone oil of the invention, fluorosilicon oil, containing hydrogen silicone oil are the polymer of low-volatile, it is to avoid use methyl
Cyclosiloxane, saves cyclosiloxane and low molecular step that high temperature removal has neither part nor lot in reaction, and product yield is high.
Embodiment
Make further details of explanation to the present invention with reference to embodiment, but the implementation of the present invention is not limited to this.
Embodiment 1
Under conditions of stirring (rotating speed of stirring is 80 revs/min), 200g viscosity 5mPa.s is added into 2L three-necked flasks
Methyl-silicone oil (molecular weight 800), 200g octaphenylcyclotetrasiloxanes and 100g viscosity 5mPa.s methyl fluorosilicon oil (molecular weight
730) 0.25g potassium hydroxide, is added, stirring 10min is mixed；150 DEG C are warming up to, constant temperature stirring 8h stops heating, is cooled to
Room temperature, adds the containing hydrogen silicone oil (molecular weight 4800) of the 20g concentrated sulfuric acids (mass concentration is 98%) and 500g hydrogen contents 1.6%, room
Warm balanced reaction 4h, is added in 80g sodium carbonate and 1h, and vacuum filtration obtains the fluorine-containing phenyl hydrogen-containing silicon oil of water white transparency.Weigh
950g, its yield is 95%.Refractive index at 25 DEG C of the silicone oil is 1.4644, viscosity 35mPa.s, hydrogen content 0.79%.
Embodiment 2
Under conditions of stirring (rotating speed of stirring is 100 revs/min), 200g viscosity is added into 2L three-necked flasks
The fluoromethane silicon of 10mPa.s methyl-silicone oil (molecular weight 1300), 200g octaphenylcyclotetrasiloxanes and 100g viscosity 50mPa.s
Oily (molecular weight 3500), adds 0.5g potassium hydroxide, and stirring 10min is mixed；160 DEG C are warming up to, constant temperature stirring 7h stops adding
Heat, is cooled to room temperature, adds the containing hydrogen silicone oil (molecular weight of the 50g concentrated sulfuric acids (mass concentration is 98%) and 500g hydrogen contents 0.6%
5000), equilibrium at room temperature reaction 5h, is added in 100g sodium carbonate and 2h, and vacuum filtration obtains water white transparency Silicon Containing Hydrogen containing fluorophenyl
Oil.Weigh 955g, and its yield is 95.5%.Refractive index at 25 DEG C of the silicone oil is 1.4641, viscosity 55mPa.s, hydrogen content
0.28%.
Embodiment 3
Under conditions of stirring (rotating speed of stirring is 120 revs/min), 150g viscosity is added into 2L three-necked flasks
The fluoromethane of 50mPa.s methyl-silicone oil (molecular weight 3800), 250g octaphenylcyclotetrasiloxanes and 100g viscosity 100mPa.s
Silicone oil (molecular weight 5500), adds 0.25g lithium hydroxides, and stirring 8min is mixed；180 DEG C are warming up to, constant temperature stirring 5h stops
Heating, is cooled to room temperature, adds the containing hydrogen silicone oil (molecule of the 18g concentrated sulfuric acids (mass concentration is 98%) and 100g hydrogen contents 1.6%
4800), equilibrium at room temperature reaction 6h adds in 54g sodium acid carbonates and 1.5h, vacuum filtration, obtains water white transparency containing fluorophenyl amount
Containing hydrogen silicone oil.Weigh 952g, and its yield is 95.2%.Refractive index at 25 DEG C of the silicone oil is 1.4932, viscosity 176mPa.s, is contained
Hydrogen amount 0.26%.
Embodiment 4
Under conditions of stirring (rotating speed of stirring is 120 revs/min), 100g viscosity is added into 2L three-necked flasks
The fluoromethane silicon of 20mPa.s methyl-silicone oil (molecular weight 2000), 250g octaphenylcyclotetrasiloxanes and 150g viscosity 75mPa.s
Oily (molecular weight 4600), adds 0.3g lithium hydroxides, stirs 8min.170 DEG C are warming up to, constant temperature stirring 5h stops heating, cold
But to room temperature, the containing hydrogen silicone oil (molecular weight of the 30g concentrated sulfuric acids (mass concentration is 98%) and 100g hydrogen contents 1.0% is added
4800), equilibrium at room temperature reaction 6h, is added in 70g sodium carbonate and 2h, and vacuum filtration obtains water white transparency Silicon Containing Hydrogen containing fluorophenyl
Oil.Weigh 950g, and its yield is 95%.Refractive index at 25 DEG C of the silicone oil is 1.4857, viscosity 125mPa.s, hydrogen content
0.16%.
Embodiment 5
Under conditions of stirring (rotating speed of stirring is 150 revs/min), 50g viscosity 5mPa.s is added into 2L three-necked flasks
Methyl-silicone oil (molecular weight 800), 250g octaphenylcyclotetrasiloxanes and 200g viscosity 25mPa.s hydroxy terminated fluorosilicone oil (molecule
2600) amount, adds 0.5g lithium hydroxides, and stirring 7min is mixed；150 DEG C are warming up to, constant temperature stirring 7h stops heating, cooling
To room temperature, the containing hydrogen silicone oil (molecular weight 5000) of the 40g concentrated sulfuric acids (mass concentration is 98%) and 500g hydrogen contents 0.1% is added,
Equilibrium at room temperature reacts 6h, adds in 100g sodium acid carbonates and 1h, and vacuum filtration obtains the fluorine-containing phenyl hydrogen-containing silicon oil of water white transparency.
Weigh 924g, its yield 92.4%.Refractive index at 25 DEG C of the silicone oil is 1.4574, viscosity 38mPa.s, hydrogen content 0.049%.
Embodiment 6
Under conditions of stirring (rotating speed of stirring is 150 revs/min), 400g viscosity is added into 2L three-necked flasks
The hydroxy terminated fluorosilicone oil of 10mPa.s methyl-silicone oil (molecular weight 1300), 75g octaphenylcyclotetrasiloxanes and 25g viscosity 5mPa.s
(molecular weight 700), adds 0.35g potassium hydroxide, and stirring 6min is mixed；160 DEG C are warming up to, constant temperature stirring 6h stops heating,
Room temperature is cooled to, the containing hydrogen silicone oil (molecular weight of the 15g concentrated sulfuric acids (mass concentration is 98%) and 200g hydrogen contents 1.6% is added
4800), equilibrium at room temperature reaction 5h, is added in 50g sodium acid carbonates and 1h, and vacuum filtration obtains water white transparency hydrogeneous containing fluorophenyl
Silicone oil.Weigh 913g, and its yield is 91.3%.Refractive index at 25 DEG C of the silicone oil is 1.4221, viscosity 16mPa.s, hydrogen content
0.45%.
Embodiment 7
Under conditions of stirring (rotating speed of stirring is 180 revs/min), 150g viscosity is added into 2L three-necked flasks
The hydroxyl fluorine silicon of 20mPa.s methyl-silicone oil (molecular weight 2000), 200g octaphenylcyclotetrasiloxanes and 150g viscosity 5mPa.s
Oily (molecular weight 700), adds 0.25g cesium hydroxides, and stirring 5min is mixed；160 DEG C are warming up to, constant temperature stirring 5h stops adding
Heat, is cooled to room temperature, adds the containing hydrogen silicone oil (molecular weight of the 26g concentrated sulfuric acids (mass concentration is 98%) and 300g hydrogen contents 1.2%
4000), equilibrium at room temperature reaction 4h, is added in 60g sodium carbonate and 1h, and vacuum filtration obtains water white transparency Silicon Containing Hydrogen containing fluorophenyl
Oil.Weigh 918g, yield 91.8%.Refractive index at 25 DEG C of the silicone oil is 1.4456, viscosity 33mPa.s, hydrogen content 0.45%.
Embodiment 8
Under conditions of stirring (rotating speed of stirring is 200 revs/min), 125g viscosity is added into 2L three-necked flasks
The fluoromethane silicon of 50mPa.s methyl-silicone oil (molecular weight 3800), 200g octaphenylcyclotetrasiloxanes and 175g viscosity 50mPa.s
Oily (molecular weight 3500), adds 0.45g cesium hydroxides, stirs；150 DEG C are heated to, constant temperature stirring 7h stops heating,
Room temperature is cooled to, the containing hydrogen silicone oil (molecular weight of the 45g concentrated sulfuric acids (mass concentration is 98%) and 500g hydrogen contents 1.0% is added
6000), equilibrium at room temperature reaction 6h, is added in 100g sodium carbonate and 1.5h, and vacuum filtration obtains water white transparency hydrogeneous containing fluorophenyl
Silicone oil.Weigh 932g, and its yield is 93.2%.Refractive index at 25 DEG C of the silicone oil is 1.4438, viscosity 76mPa.s, hydrogen content
0.48%.
Claims (9)
1. a kind of preparation method of fluorine-containing phenyl hydrogen-containing silicon oil crosslinking agent, it is characterised in that：Specifically include following steps：
Base catalyst is added into low viscosity methyl-silicone oil, phenyl ring siloxane and fluorosilicon oil, is mixed, is heated up and constant temperature stirring,
Cooling, sequentially adds acid catalyst and containing hydrogen silicone oil, and balanced reaction carries out subsequent treatment after having reacted, obtains water white transparency and contain
Fluorophenyl containing hydrogen silicone oil crosslinking agent.
2. the preparation method of fluorine-containing phenyl hydrogen-containing silicon oil crosslinking agent according to claim 1, it is characterised in that：Described is low viscous
Spend the dimethyl silicone polymer that methyl-silicone oil is methyl blocking, when its molecular weight is 800~4000,25 DEG C viscosity be 5~
50mPa.s；
Described phenyl ring siloxane is octaphenylcyclotetrasiloxane or one kind in tetramethyl tetraphenyl cyclotetrasiloxane or two
Kind；
Described fluorosilicon oil is the dimethyl silicone polymer containing trifluoropropyl group of hydroxyl or methyl blocking, its molecular weight 1000
Viscosity is 5~100mPa.s at~6000,25 DEG C；
Described containing hydrogen silicone oil be the dimethyl silicone polymer containing hydrogen-based, molecular weight 4000~6000, hydrogen content 0.1~
1.6%.
3. the preparation method of fluorine-containing phenyl hydrogen-containing silicon oil crosslinking agent according to claim 1, it is characterised in that：In low viscosity first
In base silicone oil, phenyl ring siloxane, fluorosilicon oil, the mass percent of the low viscosity methyl-silicone oil is 10~80%, benzyl ring
The mass percent of siloxanes is that the mass percent of 15~50%, fluorosilicon oil is 5~40%.
4. the preparation method of fluorine-containing phenyl hydrogen-containing silicon oil crosslinking agent according to claim 1, it is characterised in that：The Silicon Containing Hydrogen
The quality of oil is the 20~100% of low viscosity methyl-silicone oil, phenyl ring siloxane and fluorosilicon oil gross mass.
5. the preparation method of fluorine-containing phenyl hydrogen-containing silicon oil crosslinking agent according to claim 1, it is characterised in that：The heating is
Finger is warming up to 150~180 DEG C, and the time of the constant temperature stirring is 5~8h, and the mixing speed is 80~200 revs/min；It is described
The balanced reaction time is 4~6h, and the temperature of the balanced reaction is room temperature；The temperature of the cooling is room temperature.
6. the preparation method of fluorine-containing phenyl hydrogen-containing silicon oil crosslinking agent according to claim 1, it is characterised in that：The follow-up place
Reason refers to after balanced reaction to neutralize reaction solution using nertralizer, then is filtered by vacuum；The nertralizer consumption is acid
2~4 times of catalyst quality, the neutralization time is 1~2h；Described nertralizer is sodium carbonate or sodium acid carbonate.
7. the preparation method of fluorine-containing phenyl hydrogen-containing silicon oil crosslinking agent according to claim 1, it is characterised in that：Described alkali is urged
Agent is lithium hydroxide, potassium hydroxide or cesium hydroxide；Described acid catalyst is the concentrated sulfuric acid, trifluoromethanesulfonic acid, to toluene sulphur
Acid.
8. the preparation method of fluorine-containing phenyl hydrogen-containing silicon oil crosslinking agent according to claim 1, it is characterised in that：The base catalysis
The consumption of agent is the 0.05~0.1% of low viscosity methyl-silicone oil, phenyl ring siloxane and fluorosilicon oil gross mass；The acid catalyst
Consumption be low viscosity methyl-silicone oil, phenyl ring siloxane, the 2~5% of fluorosilicon oil and containing hydrogen silicone oil gross mass.
9. the fluorine-containing phenyl hydrogen-containing silicon oil crosslinking agent that a kind of preparation method as described in any one of claim 1~8 is prepared.
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| CN106674523B (en) * | 2016-12-02 | 2019-06-18 | 华南理工大学 | A kind of LED encapsulation preparation method of aminomethyl phenyl epoxy modified polysiloxane |
| CN109749084B (en) * | 2018-12-28 | 2021-04-20 | 广州福泽新材料有限公司 | Preparation method of fluorobenzene modified silicone oil |
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