CN105111446A - Fluorine-contained phenyl hydrogen-contained silicone oil cross-linking agent and preparing method thereof - Google Patents
Fluorine-contained phenyl hydrogen-contained silicone oil cross-linking agent and preparing method thereof Download PDFInfo
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Abstract
The invention belongs to the technical field of cross-linking agents and discloses a fluorine-contained phenyl hydrogen-contained silicone oil cross-linking agent and a preparing method thereof. According to the method, a base catalyst is added into low-viscosity methyl silicone oil, phenyl cyclosiloxane and fluorosilicone oil, the mixture is mixed uniformly, temperature is raised, the mixture is stirred at constant temperature and cooled, an acid catalyst and hydrogen-contained silicone oil are sequentially added into the mixture, a balanced reaction is carried out, and follow-up treatment is carried out after the reaction is finished, so that the colorless and transparent fluorine-contained phenyl hydrogen-contained silicone oil cross-linking agent is obtained. According to the preparing method, methyl cyclosiloxane and an end-capping agent do not needed to be added, the technology is simplified, and the product quality and stability are improved; the adopted raw materials do not contain chlorine or alkoxy, and therefore introduction of chloride ions and residues of alkoxy are avoided; as no solvent is adopted, harm to the human body and pollution to the environment are avoided; the yield of the prepared cross-linking agent is high.
Description
Technical field
The invention belongs to the technical field of linking agent, relate to a kind of fluorine-containing phenyl hydrogen-containing silicon oil linking agent, be specifically related to a kind of fluorine-containing phenyl hydrogen-containing silicon oil linking agent and preparation method thereof.Described fluorine-containing phenyl hydrogen-containing silicon oil linking agent specifically refers to a kind of containing fluorine-based and phenyl comodified containing hydrogen silicone oil linking agent.
Background technology
Phenyl siloxane rubber is one of principal item of silicon rubber, has good resistant of high or low temperature, radiation resistance etc., is widely used in the fields such as electronics, machinery, aerospace.Low-phenyl silicone rubber lower temperature resistance is remarkable, also has elasticity at-110 DEG C; High phenyl siloxane rubber can at 350 DEG C of life-time service; Under gammairradiation, phenyl siloxane rubber has excellent radiation resistance.But phenyl siloxane rubber oil resistant solvent resistance is not good, limit its use under oil medium, solvent environment.
Trifluoropropyl siloxane has remarkable weathering resistance, chemical stability and water and oil-resistant because combining the double properties of silicon rubber and fluorocarbon, can be used for aircraft and automotive oil tank sealing, oil resistant pad, O type circle, oil pipe etc.Trifluoropropyl siloxane has excellent oil resistant solvent resistance, but its high temperature resistant lower performance is limited, at 200 DEG C, slow oxidation degraded will occur, produce HF gas.
Fluorine-containing phenyl siloxane rubber is fluorine-based and phenyl comodified silicon rubber, has had the feature of trifluoropropyl siloxane and phenyl siloxane rubber concurrently, compensate for respective deficiency, has excellent resistant of high or low temperature, radiation resistance, oil resistant, solvent resistance etc.
Fluorine-containing phenyl hydrogen-containing silicon oil, as the reliable linking agent of the fluorine-containing phenyl siloxane rubber of add-on type, plays decisive role to the performance of fluorine-containing phenyl siloxane rubber.
The preparation of fluorine-containing phenyl hydrogen-containing silicon oil can adopt with fluorine-containing cyclosiloxane, phenyl ring siloxane, methyl cyclosiloxane, containing hydrogen silicone oil, end-capping reagent etc. for raw material, through acid catalyzed polymerisation, neutralization, takes off the techniques such as low, synthesizes fluorine-containing phenyl hydrogen-containing silicon oil.This process can not use basic catalyst, easily cause containing hydrogen silicone oil to fall hydrogen to be cross-linked, again because phenyl ring siloxane is solid, immiscible with fluorine-containing cyclosiloxane, methyl cyclosiloxane, containing hydrogen silicone oil, and phenyl ring siloxane ring body stress is large, be difficult to open loop under acidic conditions thorough, even if extend the reaction times, be also difficult to obtain completely transparent product.
Summary of the invention
In order to overcome the shortcoming and defect of prior art, the object of the present invention is to provide the preparation method of simple, the stay-in-grade fluorine-containing phenyl hydrogen-containing silicon oil linking agent of a kind of technique.The present invention with low viscosity methyl-silicone oil for raw material, first carry out ring-opening polymerization in the basic conditions with phenyl ring siloxane, fluorosilicon oil, phenyl ring siloxane is liquefied, form clear homogeneous system, then in acid condition, add containing hydrogen silicone oil, carry out molecule aggregation rearrangement, finally neutralization, vacuum filtration obtain product, without the need to adding methyl cyclosiloxane and end-capping reagent in addition in process, need high temperature removal to have neither part nor lot in the low molecule such as the methyl cyclosiloxane of reaction after avoiding reaction, simplify technique, improve quality product and stability.
Another object of the present invention is to provide the fluorine-containing phenyl hydrogen-containing silicon oil linking agent prepared by above-mentioned preparation method.
Object of the present invention is achieved by following technical proposals:
A preparation method for fluorine-containing phenyl hydrogen-containing silicon oil linking agent, specifically comprises the following steps:
In low viscosity methyl-silicone oil, phenyl ring siloxane and fluorosilicon oil, add alkaline catalysts, mixing, heat up and constant temperature stirring, cooling, adds acid catalyst and containing hydrogen silicone oil, balanced reaction successively, carry out subsequent disposal after having reacted, obtain the fluorine-containing phenyl hydrogen-containing silicon oil linking agent of water white transparency.
In low viscosity methyl-silicone oil, phenyl ring siloxane, fluorosilicon oil and containing hydrogen silicone oil, the mass percent of described low viscosity methyl-silicone oil is 10 ~ 80%, the mass percent of phenyl ring siloxane is 15 ~ 50%, the mass percent of fluorosilicon oil: 5 ~ 40%, and the quality of described containing hydrogen silicone oil is 20 ~ 100% of low viscosity methyl-silicone oil, phenyl ring siloxane and fluorosilicon oil total mass.
Described intensification refers to and is warming up to 150 ~ 180 DEG C, and the time that described constant temperature stirs is 5 ~ 8h, and described stirring velocity is 80 ~ 200 revs/min; The described balanced reaction time is 4 ~ 6h, and the temperature of described balanced reaction is room temperature; The temperature of described cooling is room temperature.
Described subsequent disposal adopts neutralizing agent to neutralize reaction solution after referring to balanced reaction, then carries out vacuum filtration.Described neutralizing agent consumption is 2 ~ 4 times of acid catalyst quality, in described and the time be 1 ~ 2h; Described neutralizing agent is sodium carbonate or sodium bicarbonate.
Described low viscosity methyl-silicone oil is the polydimethylsiloxane (molecular weight is 800 ~ 4000) of methyl blocking, and viscosity is 5 ~ 50mPa.s (25 DEG C); Under alkaline catalysts effect, there is fracture and reset with phenyl siloxane chain link, flucride siloxane chain link in molecular backbone chain, formation is evenly distributed, molecular structure simultaneously containing methylsiloxane chain link, phenyl siloxane chain link, flucride siloxane chain link, meanwhile, the end-capping reagent contained by methyl-silicone oil self has also had restriction to the viscosity of polymerisate or molecular weight.
Described phenyl ring siloxane is one or both in octaphenylcyclotetrasiloxane or tetramethyl tetraphenyl cyclotetrasiloxane.
Described fluorosilicon oil is polydimethylsiloxane (the Guangzhou Ju Tai organosilicon material company limited containing trifluoropropyl group of hydroxyl or methyl blocking, model: F-200, molecular weight 1000 ~ 6000), viscosity is 5 ~ 100mPa.s (25 DEG C).
Described containing hydrogen silicone oil is the polydimethylsiloxane (organosilicon international trade (Shanghai) Co., Ltd. of Japanese SHIN-ETSU HANTOTAI, model: KF-99, molecular weight 4000 ~ 6000) containing hydrogen base, hydrogen content 0.1 ~ 1.6%.
Described alkaline catalysts is lithium hydroxide, potassium hydroxide or cesium hydroxide.The consumption of described alkaline catalysts is 0.05 ~ 0.1% of low viscosity methyl-silicone oil, phenyl ring siloxane and fluorosilicon oil total mass.
Described acid catalyst is the vitriol oil, trifluoromethanesulfonic acid, tosic acid, is preferably the vitriol oil.The consumption of described acid catalyst is 2 ~ 5% of low viscosity methyl-silicone oil, phenyl ring siloxane, fluorosilicon oil and containing hydrogen silicone oil total mass.
Described fluorine-containing phenyl hydrogen-containing silicon oil linking agent is prepared by above-mentioned preparation method.
The present invention compared with prior art, has following beneficial effect:
(1) fluorine-containing phenyl hydrogen-containing silicon oil of the present invention preparation process in without the need to adding methyl cyclosiloxane and end-capping reagent in addition, high temperature removal is needed to have neither part nor lot in the low molecule such as the methyl cyclosiloxane of reaction after avoiding reaction, simplify technique, improve quality product and stability;
(2) fluorine-containing phenyl hydrogen-containing silicon oil of the present invention, the not chloride and alkoxyl group of the raw material adopted, avoids hydrolysis to produce a large amount of hydrochloric acid and alcohol, effectively avoids the introducing of chlorion and the residual of alkoxyl group;
(3) the present invention does not adopt any solvent, can not damage human body, can not to environment yet;
(4) methyl-silicone oil of the present invention, fluorosilicon oil, containing hydrogen silicone oil are the polymkeric substance of low-volatile, and avoid using methyl cyclosiloxane, save high temperature removal and have neither part nor lot in the cyclosiloxane of reaction and low molecular step, product yield is high.
Embodiment
Below in conjunction with embodiment, explanation detailed is further done to the present invention, but embodiments of the present invention are not limited thereto.
Embodiment 1
Under the condition stirred (rotating speed of stirring is 80 revs/min), the methyl fluoride silicone oil (molecular weight 730) of the methyl-silicone oil (molecular weight 800) of 200g viscosity 5mPa.s, 200g octaphenylcyclotetrasiloxane and 100g viscosity 5mPa.s is added in 2L there-necked flask, add 0.25g potassium hydroxide again, stir 10min mixing; Be warming up to 150 DEG C, constant temperature stirs 8h, stop heating, be cooled to room temperature, add the containing hydrogen silicone oil (molecular weight 4800) of the 20g vitriol oil (mass concentration is 98%) and 500g hydrogen content 1.6%, equilibrium at room temperature reaction 4h, adds in 80g sodium carbonate and 1h, vacuum filtration, obtains the fluorine-containing phenyl hydrogen-containing silicon oil of water white transparency.Weigh 950g, and its yield is 95%.Specific refractory power at this silicone oil 25 DEG C is 1.4644, viscosity 35mPa.s, hydrogen content 0.79%.
Embodiment 2
Under the condition stirred (rotating speed of stirring is 100 revs/min), the methyl fluoride silicone oil (molecular weight 3500) of the methyl-silicone oil (molecular weight 1300) of 200g viscosity 10mPa.s, 200g octaphenylcyclotetrasiloxane and 100g viscosity 50mPa.s is added in 2L there-necked flask, add 0.5g potassium hydroxide again, stir 10min mixing; Be warming up to 160 DEG C, constant temperature stirs 7h, stop heating, be cooled to room temperature, add the containing hydrogen silicone oil (molecular weight 5000) of the 50g vitriol oil (mass concentration is 98%) and 500g hydrogen content 0.6%, equilibrium at room temperature reaction 5h, adds in 100g sodium carbonate and 2h, vacuum filtration, obtains the fluorine-containing phenyl hydrogen-containing silicon oil of water white transparency.Weigh 955g, and its yield is 95.5%.Specific refractory power at this silicone oil 25 DEG C is 1.4641, viscosity 55mPa.s, hydrogen content 0.28%.
Embodiment 3
Under the condition stirred (rotating speed of stirring is 120 revs/min), the methyl fluoride silicone oil (molecular weight 5500) of the methyl-silicone oil (molecular weight 3800) of 150g viscosity 50mPa.s, 250g octaphenylcyclotetrasiloxane and 100g viscosity 100mPa.s is added in 2L there-necked flask, add 0.25g lithium hydroxide again, stir 8min mixing; Be warming up to 180 DEG C, constant temperature stirs 5h, stop heating, be cooled to room temperature, add the containing hydrogen silicone oil (molecular weight 4800) of the 18g vitriol oil (mass concentration is 98%) and 100g hydrogen content 1.6%, equilibrium at room temperature reaction 6h, adds in 54g sodium bicarbonate and 1.5h, vacuum filtration, obtains the fluorine-containing phenyl hydrogen-containing silicon oil of water white transparency.Weigh 952g, and its yield is 95.2%.Specific refractory power at this silicone oil 25 DEG C is 1.4932, viscosity 176mPa.s, hydrogen content 0.26%.
Embodiment 4
Under the condition stirred (rotating speed of stirring is 120 revs/min), the methyl fluoride silicone oil (molecular weight 4600) of the methyl-silicone oil (molecular weight 2000) of 100g viscosity 20mPa.s, 250g octaphenylcyclotetrasiloxane and 150g viscosity 75mPa.s is added in 2L there-necked flask, add 0.3g lithium hydroxide again, stir 8min.Be warming up to 170 DEG C, constant temperature stirs 5h, stop heating, be cooled to room temperature, add the containing hydrogen silicone oil (molecular weight 4800) of the 30g vitriol oil (mass concentration is 98%) and 100g hydrogen content 1.0%, equilibrium at room temperature reaction 6h, adds in 70g sodium carbonate and 2h, vacuum filtration, obtains the fluorine-containing phenyl hydrogen-containing silicon oil of water white transparency.Weigh 950g, and its yield is 95%.Specific refractory power at this silicone oil 25 DEG C is 1.4857, viscosity 125mPa.s, hydrogen content 0.16%.
Embodiment 5
Under the condition stirred (rotating speed of stirring is 150 revs/min), the hydroxy terminated fluorosilicone oil (molecular weight 2600) of the methyl-silicone oil (molecular weight 800) of 50g viscosity 5mPa.s, 250g octaphenylcyclotetrasiloxane and 200g viscosity 25mPa.s is added in 2L there-necked flask, add 0.5g lithium hydroxide again, stir 7min mixing; Be warming up to 150 DEG C, constant temperature stirs 7h, stop heating, be cooled to room temperature, add the containing hydrogen silicone oil (molecular weight 5000) of the 40g vitriol oil (mass concentration is 98%) and 500g hydrogen content 0.1%, equilibrium at room temperature reaction 6h, adds in 100g sodium bicarbonate and 1h, vacuum filtration, obtains the fluorine-containing phenyl hydrogen-containing silicon oil of water white transparency.Weigh 924g, its yield 92.4%.Specific refractory power at this silicone oil 25 DEG C is 1.4574, viscosity 38mPa.s, hydrogen content 0.049%.
Embodiment 6
Under the condition stirred (rotating speed of stirring is for being 150 revs/min), the hydroxy terminated fluorosilicone oil (molecular weight 700) of the methyl-silicone oil (molecular weight 1300) of 400g viscosity 10mPa.s, 75g octaphenylcyclotetrasiloxane and 25g viscosity 5mPa.s is added in 2L there-necked flask, add 0.35g potassium hydroxide again, stir 6min mixing; Be warming up to 160 DEG C, constant temperature stirs 6h, stop heating, be cooled to room temperature, add the containing hydrogen silicone oil (molecular weight 4800) of the 15g vitriol oil (mass concentration is 98%) and 200g hydrogen content 1.6%, equilibrium at room temperature reaction 5h, adds in 50g sodium bicarbonate and 1h, vacuum filtration, obtains the fluorine-containing phenyl hydrogen-containing silicon oil of water white transparency.Weigh 913g, and its yield is 91.3%.Specific refractory power at this silicone oil 25 DEG C is 1.4221, viscosity 16mPa.s, hydrogen content 0.45%.
Embodiment 7
Under the condition stirred (rotating speed of stirring is 180 revs/min), the hydroxy terminated fluorosilicone oil (molecular weight 700) of the methyl-silicone oil (molecular weight 2000) of 150g viscosity 20mPa.s, 200g octaphenylcyclotetrasiloxane and 150g viscosity 5mPa.s is added in 2L there-necked flask, add 0.25g cesium hydroxide again, stir 5min mixing; Be warming up to 160 DEG C, constant temperature stirs 5h, stop heating, be cooled to room temperature, add the containing hydrogen silicone oil (molecular weight 4000) of the 26g vitriol oil (mass concentration is 98%) and 300g hydrogen content 1.2%, equilibrium at room temperature reaction 4h, adds in 60g sodium carbonate and 1h, vacuum filtration, obtains the fluorine-containing phenyl hydrogen-containing silicon oil of water white transparency.Weigh 918g, yield 91.8%.Specific refractory power at this silicone oil 25 DEG C is 1.4456, viscosity 33mPa.s, hydrogen content 0.45%.
Embodiment 8
Under the condition stirred (rotating speed of stirring is 200 revs/min), the methyl fluoride silicone oil (molecular weight 3500) of the methyl-silicone oil (molecular weight 3800) of 125g viscosity 50mPa.s, 200g octaphenylcyclotetrasiloxane and 175g viscosity 50mPa.s is added in 2L there-necked flask, add 0.45g cesium hydroxide again, stir; Be heated to 150 DEG C, constant temperature stirs 7h, stop heating, be cooled to room temperature, add the containing hydrogen silicone oil (molecular weight 6000) of the 45g vitriol oil (mass concentration is 98%) and 500g hydrogen content 1.0%, equilibrium at room temperature reaction 6h, adds in 100g sodium carbonate and 1.5h, vacuum filtration, obtains the fluorine-containing phenyl hydrogen-containing silicon oil of water white transparency.Weigh 932g, and its yield is 93.2%.Specific refractory power at this silicone oil 25 DEG C is 1.4438, viscosity 76mPa.s, hydrogen content 0.48%.
Claims (9)
1. a preparation method for fluorine-containing phenyl hydrogen-containing silicon oil linking agent, is characterized in that: specifically comprise the following steps:
In low viscosity methyl-silicone oil, phenyl ring siloxane and fluorosilicon oil, add alkaline catalysts, mixing, heat up and constant temperature stirring, cooling, adds acid catalyst and containing hydrogen silicone oil, balanced reaction successively, carry out subsequent disposal after having reacted, obtain the fluorine-containing phenyl hydrogen-containing silicon oil linking agent of water white transparency.
2. the preparation method of fluorine-containing phenyl hydrogen-containing silicon oil linking agent according to claim 1, it is characterized in that: described low viscosity methyl-silicone oil is the polydimethylsiloxane of methyl blocking, when its molecular weight is 800 ~ 4000,25 DEG C, viscosity is 5 ~ 50mPa.s;
Described phenyl ring siloxane is one or both in octaphenylcyclotetrasiloxane or tetramethyl tetraphenyl cyclotetrasiloxane;
Described fluorosilicon oil is the polydimethylsiloxane containing trifluoropropyl group of hydroxyl or methyl blocking, and during its molecular weight 1000 ~ 6000,25 DEG C, viscosity is 5 ~ 100mPa.s;
Described containing hydrogen silicone oil is the polydimethylsiloxane containing hydrogen base, molecular weight 4000 ~ 6000, hydrogen content 0.1 ~ 1.6%.
3. the preparation method of fluorine-containing phenyl hydrogen-containing silicon oil linking agent according to claim 1, it is characterized in that: in low viscosity methyl-silicone oil, phenyl ring siloxane, fluorosilicon oil, the mass percent of described low viscosity methyl-silicone oil is 10 ~ 80%, the mass percent of phenyl ring siloxane is 15 ~ 50%, the mass percent of fluorosilicon oil is 5 ~ 40%.
4. the preparation method of fluorine-containing phenyl hydrogen-containing silicon oil linking agent according to claim 1, is characterized in that: the quality of described containing hydrogen silicone oil is 20 ~ 100% of low viscosity methyl-silicone oil, phenyl ring siloxane and fluorosilicon oil total mass.
5. the preparation method of fluorine-containing phenyl hydrogen-containing silicon oil linking agent according to claim 1, is characterized in that: described intensification refers to and is warming up to 150 ~ 180 DEG C, and the time that described constant temperature stirs is 5 ~ 8h, and described stirring velocity is 80 ~ 200 revs/min; The described balanced reaction time is 4 ~ 6h, and the temperature of described balanced reaction is room temperature; The temperature of described cooling is room temperature.
6. the preparation method of fluorine-containing phenyl hydrogen-containing silicon oil linking agent according to claim 1, is characterized in that: described subsequent disposal adopts neutralizing agent to neutralize reaction solution after referring to balanced reaction, then carries out vacuum filtration; Described neutralizing agent consumption is 2 ~ 4 times of acid catalyst quality, in described and the time be 1 ~ 2h; Described neutralizing agent is sodium carbonate or sodium bicarbonate.
7. the preparation method of fluorine-containing phenyl hydrogen-containing silicon oil linking agent according to claim 1, is characterized in that: described alkaline catalysts is lithium hydroxide, potassium hydroxide or cesium hydroxide; Described acid catalyst is the vitriol oil, trifluoromethanesulfonic acid, tosic acid.
8. the preparation method of fluorine-containing phenyl hydrogen-containing silicon oil linking agent according to claim 1, is characterized in that: the consumption of described alkaline catalysts is 0.05 ~ 0.1% of low viscosity methyl-silicone oil, phenyl ring siloxane and fluorosilicon oil total mass; The consumption of described acid catalyst is 2 ~ 5% of low viscosity methyl-silicone oil, phenyl ring siloxane, fluorosilicon oil and containing hydrogen silicone oil total mass.
9. the fluorine-containing phenyl hydrogen-containing silicon oil linking agent prepared by the preparation method described in any one of claim 1 ~ 8.
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