CN101824150A - Aryl-containing polysiloxane and preparation method thereof - Google Patents
Aryl-containing polysiloxane and preparation method thereof Download PDFInfo
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- CN101824150A CN101824150A CN200910025649A CN200910025649A CN101824150A CN 101824150 A CN101824150 A CN 101824150A CN 200910025649 A CN200910025649 A CN 200910025649A CN 200910025649 A CN200910025649 A CN 200910025649A CN 101824150 A CN101824150 A CN 101824150A
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Abstract
The invention relates to an aryl-containing polysiloxane and a preparation method thereof. The method comprises the following steps of: performing hydrosilylation reaction of a hydrogenous ring or a hydrogenous oligomer and an aromatic compound aromatic compound which has independent double links to introduce aryl to an organosilicone molecular structure to obtain an aryl-containing organosilicone monomer or prepolymer; and then, copolymerizing the aryl-containing organosilicone monomer or prepolymer with other organosilicone rings to obtain the phenyl or aryl-containing polysiloxane. The method adopts available raw materials, low cost, mild reaction conditions and a simple process; and the prepared polysiloxane has wide application prospect in LED encapsulation, high-temperature heat carrier, isolation and anti-sticking, instrument liquid transfer, cosmetics and other fields.
Description
Technical field
The invention belongs to chemical technology field, be specifically related to a kind of polysiloxane that contains aromatic group and preparation method thereof.
Background technology
Phenyl polysiloxane is one of principal item of polysiloxane, owing to introduced aromatic groups such as phenyl in its molecular chain, made it have better resistance to elevated temperatures, radiation resistance than methyl polysiloxane, lubricity and solubility property, working temperature-50 ℃～250 ℃.In addition, it also has good chemical stability, insulativity, hydrophobic nature and physiology inertia etc., be widely used in fields such as electronics, household chemicals, weaving, machinery, automobile, as insulation, lubricated, damping, shockproof, dustproof and elevated temperature heat carrier etc.
Tradition phenyl polysiloxane synthetic technology mainly contains two kinds of hydrolytic condensation and ring-opening polymerizations:
1, hydrolytic condensation
By cohydrolysis condensation prepared such as phenyl chlorosilane, methyl chlorosilane, vinyl chlorosilane etc. or octadecyloxy phenyl TMOS and other alkoxyl group organosilane monomers;
2, ring-opening polymerization
Ring-opening polymerization under the effect of acidity or basic catalyst obtains by phenyl ring body and methyl, vinyl or other organosilicon ring bodies etc.
The tradition phenyl polysiloxane is in preparation process, reason such as bad and reactive behavior diversity ratio is bigger owing to the consistency of phenyl monomer and other organosilane monomers, skewness, the polymerization degree of phenyl are low in the phenyl polysiloxane that causes being obtained, consistency is poor, the system muddiness, especially for the polysiloxane of high phenyl content, all the more so.And can't satisfy the requirement of its transparency, high thermal resistance and high refractive index during as the LED packaged material when it.
Summary of the invention
The present invention is directed to above present situation, the problem that exists in phenyl polysiloxane structure and the synthetic method is analyzed, a kind of new synthetic route is proposed, promptly by the synthetic a kind of aromatic base silicone intermediate that contains of addition reaction of silicon with hydrogen, thereby the distance of aromatic group and Siliciumatom is increased, reduce sterically hindered, increase phenyl silicon monomer and other monomeric consistency and reactive behavioies, the aromatic base polysiloxane for preparing high-clarity then with other monomer copolymerizations, and provide a kind of new approaches, new way for developing synthetic high refractive index organosilicon encapsulating material.
The objective of the invention is by a kind of new and effective means-addition reaction of silicon with hydrogen, in the organosilicon molecular structure, introduce the group of aromatic group--its consistency that not only can improve raw material is with reactive, can also effectively improve refractive index, radiation resistance and the high thermal resistance of material, thereby obtain a kind of transparent aromatic base polysiloxane, in the hope of realizing its use in the LED encapsulation.
The present invention is achieved by the following technical solutions:
A kind of polysiloxane that contains aromatic group of the present invention, its density is 0.92～1.15, viscosity is 15～10 in the time of 25 ℃
5MPa, refractive index are 1.4000～1.5300 in the time of 25 ℃, and the general structure of this polysiloxane is as follows:
R wherein
1, R
2, R
3, R
4, R
6, R
7Be respectively CH
3, C
2H
5, C
3H
7, C
4H
9, H, CH=CH
2R
1, R
2, R
3, R
4, R
6And R
7Can be the same or different; R
5Be C
6H
5, C
10H
8,-C
6H
4-CH
3,-C
6H
4-Br ,-C
6H
3-(CH
3)
3Deng; 0≤n≤1.5 * 10
31≤m≤1.0 * 10
30≤p＜2 * 10
33≤n+m+p＜2 * 10
3
A kind of preparation method who contains the polysiloxane of aromatic group of the present invention may further comprise the steps:
(1) contains the organosilane monomer of aromatic base or synthesizing of prepolymer: carry out addition reaction of silicon with hydrogen by hydrogeneous ring body or hydrogeneous oligopolymer with the aromatics that contains isolated double bond and make, reaction is that step is carried out in the following order: with hydrogeneous ring body or hydrogen containing siloxane and platinum, rhodium, palladium or its compound catalyst are dissolved in the solvent together, and join in the reaction flask, temperature is adjusted between 25～120 ℃ then, the aromatics that will contain single isolated double bond slowly is added drop-wise to and carries out addition reaction in the reaction flask, dropwise and continue reaction 2～3h, finish reaction, underpressure distillation removes the reactant that desolvates and do not participate in reaction again, promptly get the aromatic base organosilane monomer, its structural formula has following two kinds:
R wherein
1, R
2, R
3, R
4Be respectively CH
3, C
2H
5, C
3H
7, C
4H
9R
1, R
2, R
3And R
4Can be the same or different; R
5Be C
6H
5, C
10H
8,-C
6H
4-CH
3,-C
6H
4-Br ,-C
6H
3-(CH
3)
3Deng; 0≤n≤300; 0＜m≤300; 3≤n+m≤300;
(2) with other organosilane monomer copolyreaction: the aromatic base organosilane monomer or prepolymer, organosilicon ring body, end-capping reagent and the catalyzer that prepare are joined in the reaction flask that has stirring, thermometer and condensing works, carry out vacuum hydro-extraction, logical nitrogen, be warming up to 70～150 ℃ then and carry out the catalytically rearranging balanced reaction, reaction is removed catalyzer after finishing, low-boiling-point substance is removed in underpressure distillation again, promptly obtains the transparent aromatic based polysiloxane.
Hydrogeneous ring body of the present invention or hydrogen containing siloxane, its general structure is:
Wherein, R
1, R
2, R
3, R
4Be respectively CH
3, C
2H
5, C
3H
7, C
4H
9R
1, R
2, R
3And R
4Can be the same or different; 0≤n≤300; 0＜m≤300; 3≤n+m≤300.
The preparation method of hydrogeneous ring body of the present invention or hydrogen containing siloxane is as follows: will contain silicon hydride chlorid and directly be added drop-wise in the water and be hydrolyzed, the hydrolysis back deacidification water layer that finishes is washed to neutrality again, hydrogeneous ring body or hydrogeneous prepolymer.
The aromatics that contains an isolated double bond of the present invention, its structural formula is:
CH
2＝CH-R
5 
R wherein
5Be C
6H
5, C
10H
8,-C
6H
4-CH
3,-C
6H
4-Br ,-C
6H
3-(CH
3)
3Deng.
Solvent of the present invention comprises toluene, dimethylbenzene, sherwood oil, chloroform etc.
Organosilicon ring body of the present invention comprises: hexamethyl cyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentaandoxane, trimethylammonium trivinyl cyclotrisiloxane, tetramethyl-tetrem thiazolinyl cyclotetrasiloxane, tetramethyl-ring tetrasiloxane, Hexaethyl cyclotrisiloxane, octaethyl cyclotetrasiloxane, methylethyl D5 etc.
End-capping reagent of the present invention comprises: tetramethyl disiloxane, dimethyl sily oxide, sily oxide, hexamethyldisiloxane, tetramethyl divinyl disiloxane, dimethyl tetrem thiazolinyl sily oxide, six vinyl sily oxide, dimethyl tetraphenyl sily oxide etc.
Catalyzer of the present invention is the vitriol oil, three fluosulfonic acid, acidic resins, acidic white earth, potassium hydroxide, Tetramethylammonium hydroxide, n-Butyl Lithium, sodium silanolate etc.
Below mode by specific embodiments, the present invention is done further detailed description, be limitation of the present invention but should not be construed as.
Embodiment
Embodiment 1:
A certain amount of 100g toluene and 300g water are poured in the three-necked flask of 1L, taken by weighing 100g dimethyl dichlorosilane (DMCS) monomer again and be dissolved in the 100g toluene; Below 25 ℃, slowly drip the mixed chlorosilane monomer solution while stirring then, dropwise, continue to stir 30min; Remove the sour water layer and be washed to neutrality with separating funnel; Last underpressure distillation removes anhydrates and toluene and unreacted monomer, obtains hydrogeneous ring body.Be dissolved in the hydrogeneous ring body 60g that obtains and catalyzer (1% isopropyl alcohol solution of chloroplatinic acid) 0.12g in the 100g toluene jointly and add in the three-necked flask logical nitrogen 30min; Be warming up to 70 ℃ then, beginning slowly drips 120g vinylbenzene, dropwises the back and continues reaction 3h; Unreacted vinylbenzene is completely removed in underpressure distillation again, obtains water white aromatic base organosilane monomer A.
The aromatic base organosilane monomer A that obtains is mixed with octamethylcyclotetrasiloxane, tetramethyl divinyl disiloxane and Tetramethylammonium hydroxide and join in the reaction flask that has stirring, thermometer and condensing works, carry out vacuum hydro-extraction, logical nitrogen is then 80 ℃ of catalytically rearranging balanced reactions of carrying out 6h; Reaction finishes to be warming up to 170 ℃ and removes catalyzer, at 1.35Kpa200 ℃ of following underpressure distillation 2h, removes low-boiling-point substance, can obtain transparent polysiloxane, and viscosity is 3700mPaS, and refractive index is 1.5136, productive rate 89.7%.
Embodiment 2:
Aromatic base organosilane monomer A method for making is with embodiment 1, gained aromatic base organosilane monomer A is mixed with octamethylcyclotetrasiloxane, tetramethyl-tetrem thiazolinyl cyclotetrasiloxane, tetramethyl divinyl disiloxane and Tetramethylammonium hydroxide and join in the reaction flask that has stirring, thermometer and condensing works, carry out vacuum hydro-extraction, logical nitrogen is then 80 ℃ of catalytically rearranging balanced reactions of carrying out 6h; Reaction finishes to be warming up to 170 ℃ and removes catalyzer, at 1.35Kpa200 ℃ of following underpressure distillation 2h, removes low-boiling-point substance, can obtain transparent polysiloxane, and viscosity is 5600mPaS, and refractive index is 1.4824, productive rate 90.2%.
Embodiment 3:
Aromatic base organosilane monomer A method for making is with embodiment 1, gained aromatic base organosilane monomer A is joined in the reaction flask that has stirring, thermometer and condensing works with octamethylcyclotetrasiloxane, tetramethyl-ring tetrasiloxane, tetramethyl-tetrem thiazolinyl cyclotetrasiloxane, tetramethyl divinyl disiloxane and strong-acid ion exchange resin, carry out vacuum hydro-extraction, logical nitrogen is then 90 ℃ of catalytically rearranging balanced reactions of carrying out 6h; Reaction finishes to remove by filter catalyzer, at 1.35Kpa200 ℃ of following underpressure distillation 2h, removes low-boiling-point substance, can obtain transparent polysiloxane, and viscosity is 269mPaS, and refractive index is 1.4580, productive rate 89.2%.
Embodiment 4:
A certain amount of 100g toluene and 300g water are poured in the three-necked flask of 1L, taken by weighing 100g dimethyl dichlorosilane (DMCS) monomer again and be dissolved in the 100g toluene; Below 25 ℃, slowly drip the mixed chlorosilane monomer solution while stirring then, dropwise, continue to stir 30min; Remove the sour water layer and be washed to neutrality with separating funnel; Last underpressure distillation removes anhydrates and toluene and unreacted monomer, obtains hydrogeneous ring body.The hydrogeneous ring body 60g and catalyzer (1% isopropyl alcohol solution of chloroplatinic acid) 0.24 gram that obtain are dissolved in the 100g toluene, add in the three-necked flask logical nitrogen 30min; Be warming up to 90 ℃ then, beginning slowly drips the 135g alpha-methyl styrene, dropwises the back and continues reaction 3h; Unreacted vinylbenzene is completely removed in underpressure distillation again, obtains water white aromatic base organosilane monomer B.
The aromatic base organosilane monomer B that obtains is joined in the reaction flask that has stirring, thermometer and condensing works with octamethylcyclotetrasiloxane, tetramethyl-ring tetrasiloxane, hexamethyldisiloxane and strong-acid ion exchange resin, carry out vacuum hydro-extraction, logical nitrogen is then 90 ℃ of catalytically rearranging balanced reactions of carrying out 6h; Reaction finishes to remove by filter catalyzer, at 1.35Kpa200 ℃ of following underpressure distillation 2h, removes low-boiling-point substance, can obtain transparent polysiloxane, and viscosity is 269mPaS, and refractive index is 1.4992, productive rate 87.4%.
Claims (9)
1. polysiloxane that contains aromatic group, it is characterized in that: density is 0.92～1.15, viscosity is 15～10 in the time of 25 ℃
5MPa, refractive index are 1.4000～1.5300 in the time of 25 ℃, and this polysiloxane has following structure:
R wherein
1, R
2, R
3, R
4, R
6, R
7Be respectively CH
3, C
2H
5, C
3H
7, C
4H
9, H, CH=CH
2R
1, R
2, R
3, R
4, R
6And R
7Can be the same or different; R
5Be C
6H
5, C
10H
8,-C
6H
4-CH
3,-C
6H
4-Br ,-C
6H
3-(CH
3)
3Deng; 0≤n≤1.5 * 10
31≤m≤1.0 * 10
30≤p＜2 * 10
33≤n+m+p＜2 * 10
3
2. preparation method who contains the polysiloxane of aromatic group is characterized in that: may further comprise the steps:
(1) contains the organosilane monomer of aromatic base or synthesizing of prepolymer: carry out addition reaction of silicon with hydrogen by hydrogeneous ring body or hydrogeneous oligopolymer with the aromatics that contains isolated double bond and make, reaction is that step is carried out in the following order: with hydrogeneous ring body or hydrogen containing siloxane and platinum, rhodium, palladium or its compound catalyst are dissolved in the solvent together, and join in the reaction flask, adjust then between temperature to 25～120 ℃, the aromatics that will contain single isolated double bond slowly is added drop-wise to and carries out addition reaction in the reaction flask, dropwise and continue reaction 2～3h, finish reaction, underpressure distillation removes the reactant that desolvates and do not participate in reaction again, promptly get the aromatic base organosilane monomer, its structural formula has following two kinds:
R wherein
1, R
2, R
3, R
4Be respectively CH
3, C
2H
5, C
3H
7, C
4H
9R
1, R
2, R
3And R
4Can be the same or different; R
5Be C
6H
5, C
10H
8,-C
6H
4-CH
3,-C
6H
4-Br ,-C
6H
3-(CH
3)
3Deng; 0≤n≤300; 0＜m≤300; 3≤n+m≤300;
(2) with other organosilane monomer copolyreaction: the aromatic base organosilane monomer or prepolymer, organosilicon ring body, end-capping reagent and the catalyzer that prepare are joined in the reaction flask that has stirring, thermometer and condensing works, carry out vacuum hydro-extraction, logical nitrogen, be warming up to 70～150 ℃ then and carry out the catalytically rearranging balanced reaction, reaction is removed catalyzer after finishing, low-boiling-point substance is removed in underpressure distillation again, promptly obtains the transparent aromatic based polysiloxane.
3. the preparation method who contains the polysiloxane of aromatic group according to claim 2 is characterized in that: described hydrogeneous ring body or hydrogen containing siloxane, and its structural formula is:
Wherein, R
1, R
2, R
3, R
4Be respectively CH
3, C
2H
5, C
3H
7, C
4H
9R
1, R
2, R
3And R
4Can be the same or different; 0≤n≤300; 0＜m≤300; 3n+m 300.
4. the preparation method who contains the polysiloxane of aromatic group according to claim 2, it is characterized in that: the preparation method of described hydrogeneous ring body or hydrogen containing siloxane is as follows: will contain silicon hydride chlorid and directly be added drop-wise in the water and be hydrolyzed, the deacidification water layer was washed to neutrality again after hydrolysis finished, and got hydrogeneous ring body or hydrogeneous prepolymer.
5. the preparation method who contains the polysiloxane of aromatic group according to claim 2 is characterized in that: the described aromatics that contains an isolated double bond, and its structural formula is:
CH
2＝CH-R
5 
R wherein
5Be C
6H
5, C
10H
8,-C
6H
4-CH
3,-C
6H
4-Br ,-C
6H
3-(CH
3)
3Deng.
6. the preparation method who contains the polysiloxane of aromatic group according to claim 2 is characterized in that: described solvent comprises toluene, dimethylbenzene, sherwood oil, chloroform etc.
7. the preparation method who contains the polysiloxane of aromatic group according to claim 2 is characterized in that: described organosilicon ring body comprises: hexamethyl cyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentaandoxane, trimethylammonium trivinyl cyclotrisiloxane, tetramethyl-tetrem thiazolinyl cyclotetrasiloxane, tetramethyl-ring tetrasiloxane, Hexaethyl cyclotrisiloxane, octaethyl cyclotetrasiloxane, methylethyl D5 etc.
8. the preparation method who contains the polysiloxane of aromatic group according to claim 2 is characterized in that: described end-capping reagent comprises: tetramethyl disiloxane, dimethyl sily oxide, sily oxide, hexamethyldisiloxane, tetramethyl divinyl disiloxane, dimethyl tetrem thiazolinyl sily oxide, six vinyl sily oxide, dimethyl tetraphenyl sily oxide etc.
9. the preparation method who contains the polysiloxane of aromatic group according to claim 2 is characterized in that described catalyzer is the vitriol oil, three fluosulfonic acid, acidic resins, acidic white earth, potassium hydroxide, Tetramethylammonium hydroxide, n-Butyl Lithium, sodium silanolate etc.
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|---|---|---|---|
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Family
ID=42688330
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101974157A (en) * | 2010-11-02 | 2011-02-16 | 中昊晨光化工研究院 | Synthesis method of phenyl hydrogen-containing silicone oil |
| CN102408565A (en) * | 2011-09-09 | 2012-04-11 | 汕头市骏码凯撒有限公司 | Preparation method for phenyl hydrogen-containing silicone oil |
| CN104861168A (en) * | 2015-05-05 | 2015-08-26 | 深圳新宙邦科技股份有限公司 | Phenyl hydrogen silicone oil for LED (Light Emitting Diode) encapsulation adhesive and preparation method thereof |
| CN107619462A (en) * | 2017-10-16 | 2018-01-23 | 德清舒华泡沫座椅有限公司 | A kind of flame-retardant high-elasticity polyurethane foam |
| CN108842461A (en) * | 2018-06-26 | 2018-11-20 | 湖北新海鸿化工有限公司 | A kind of fabric softener intermediate and preparation method thereof |
| CN112280309A (en) * | 2020-11-11 | 2021-01-29 | 株洲时代新材料科技股份有限公司 | Damping agent for silicon rubber, silicon rubber material and preparation method thereof |
| CN113402711A (en) * | 2021-05-17 | 2021-09-17 | 洛阳理工学院 | Preparation method of methyl styryl silicone oil |
-
2009
- 2009-03-03 CN CN200910025649A patent/CN101824150A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101974157A (en) * | 2010-11-02 | 2011-02-16 | 中昊晨光化工研究院 | Synthesis method of phenyl hydrogen-containing silicone oil |
| CN101974157B (en) * | 2010-11-02 | 2012-07-04 | 中昊晨光化工研究院 | Synthesis method of phenyl hydrogen-containing silicone oil |
| CN102408565A (en) * | 2011-09-09 | 2012-04-11 | 汕头市骏码凯撒有限公司 | Preparation method for phenyl hydrogen-containing silicone oil |
| CN102408565B (en) * | 2011-09-09 | 2013-04-24 | 汕头市骏码凯撒有限公司 | Preparation method for phenyl hydrogen-containing silicone oil |
| CN104861168A (en) * | 2015-05-05 | 2015-08-26 | 深圳新宙邦科技股份有限公司 | Phenyl hydrogen silicone oil for LED (Light Emitting Diode) encapsulation adhesive and preparation method thereof |
| CN107619462A (en) * | 2017-10-16 | 2018-01-23 | 德清舒华泡沫座椅有限公司 | A kind of flame-retardant high-elasticity polyurethane foam |
| CN108842461A (en) * | 2018-06-26 | 2018-11-20 | 湖北新海鸿化工有限公司 | A kind of fabric softener intermediate and preparation method thereof |
| CN112280309A (en) * | 2020-11-11 | 2021-01-29 | 株洲时代新材料科技股份有限公司 | Damping agent for silicon rubber, silicon rubber material and preparation method thereof |
| CN113402711A (en) * | 2021-05-17 | 2021-09-17 | 洛阳理工学院 | Preparation method of methyl styryl silicone oil |
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Open date: 20100908 |