CN104672455A - Preparation method of methylphenyl hydrogen-containing silicone oil - Google Patents
Preparation method of methylphenyl hydrogen-containing silicone oil Download PDFInfo
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- CN104672455A CN104672455A CN201310638772.3A CN201310638772A CN104672455A CN 104672455 A CN104672455 A CN 104672455A CN 201310638772 A CN201310638772 A CN 201310638772A CN 104672455 A CN104672455 A CN 104672455A
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Abstract
The invention provides a colorless transparent high-refractivity methylphenyl hydrogen-containing silicone oil, which is prepared by cyclosiloxane ring-opening polymerization under the catalytic action of strong acid and is completely compatible with phenylvinyl silicone oil or phenylvinyl silicone resin. The methylphenyl hydrogen-containing silicone oil is used as a crosslinking agent for LED (light-emitting diode) packaging materials.
Description
Technical field
The present invention relates to a kind of preparation method of containing hydrogen silicone oil, specifically refer to a kind of preparation method of phenyl hydrogen-containing silicon oil
Background technology
Along with the development of human society, physical environment constantly worsens, and incident energy problem, environmental problem also become increasingly conspicuous, and how save energy has become is put the problem cannot avoided in face of people.According to statistics, only throw light at present and just account for 20% of whole world total energy consumption, lower, that the life-span the is longer environment-friendly type new light sources of employing energy consumption replaces the important channel that traditional high power consumption light source addresses this problem beyond doubt.Light emitting diode (Light Emitting Diode), be called for short LED, it is a kind of semiconductive luminescent materials, its light-emitting device is a kind of emerging eco-friendly power source, current each state is all wideling popularize, and is expected to the forth generation light source become after incandescent light, luminescent lamp, high-intensity gas discharge lamp.In the integral part of LED, its encapsulating structure and packaging plastic play vital effect to product quality, organo-silicone rubber and silicone resin are the desirable encapsulation auxiliary materials of LED, and the exploitation of the optical grade flexible silicone packaged material that high refractive power, high printing opacity, radiation hardness, high heat conduction can eliminate stress and industrialization are China's Semiconductor Lighting urgent problems.
A key link in the research and development of organosilicon LED encapsulation material is exactly the containing hydrogen silicone oil of synthesis high refractive index, high transmission rate, and claimed structure evenly, highly transparent and specific refractory power be more than 1.5.The LED methyl and phenyl hydrogen-containing silicon oil reported both at home and abroad is at present all by forming containing silicon hydride chlorid and non-hydrogeneous hydrolyzing chlorosilane polycondensation, containing the containing hydrogen silicone oil of phenylbenzene silica chain link, the method is repeated and controllability is all poor, all need with organic solvent simultaneously, all unfavorable factor is existed to safety and Health.CN101974157B and CN102408565B adopts organic solvent syntheti c route, there is the drawbacks such as production operation safety and environment protection, and is unfavorable for stay-in-grade product configuration.Chinese patent CN101289538B discloses a kind of preparation method of LED methyl and phenyl hydrogen-containing silicon oil.The method uses Zeo-karb as catalyzer, because its acidity is lower, catalytic process Middle molecule is reset abundant not, other components of product and packaging plastic are made to there is the imperfect problem of consistency, have impact on the transmittance of product, simultaneously because resin catalysis active centre, in aperture, is only suitable for the molecule of certain size, the more full-bodied methyl and phenyl hydrogen-containing silicon oil of very difficult acquisition, thus reduce product quality.
Chinese patent CN101851333B discloses a kind of method utilizing preparing methyl phenyl hydrogen-containing silicone oil by rare earth super acid catalysis, overcomes the acid weak defect of Zeo-karb, but catalyst preparation process is complicated and cost is high, and the hydrogen content of product is low simultaneously.
Summary of the invention
There are the problems referred to above such as pollution problem for LED encapsulation material complicated process of preparation in prior art, the invention provides the ring-opening polymerization of a kind of strong acid catalyst cyclosiloxane prepare water white transparency and with the phenyl-vinyl silicon oil of high refractive index or the completely compatible methyl and phenyl hydrogen-containing silicon oil of phenyl vinyl polysiloxane, as the linking agent of LED encapsulation material.
The present invention is achieved through the following technical solutions:
1) by methyl phenyl ring siloxane D
m me, Ph(m=3,4,5) decompression dehydration, then adds methylhydracyclosiloxane D
n h(n=3,4,5), end-capping reagent, under the catalysis of strong acid catalyst, carry out ring-opening copolymerization reaction, reaction expression is as follows:
Wherein D
m me, Ph, D
n hchemical structural formula is as follows
2), after polymerization, with sodium bicarbonate neutralization, filter afterwards, by the clear liquid removed under reduced pressure low molecular compound of gained, be then cooled to room temperature, obtain water white liquid, be methyl and phenyl hydrogen-containing silicon oil.
Polymeric reaction temperature is 30-80 DEG C, and polymerization time is 1-6h; As preferably, described temperature of reaction is 50-60 DEG C, and polymerization reaction time is 3-5h.
Described raw material methylhydracyclosiloxane in advance can be dry through Calcium Chloride Powder Anhydrous.
Used catalyst is one or more in sulfuric acid, hydrochloric acid, nitric acid, perchloric acid, Phenylsulfonic acid, p-methyl benzenesulfonic acid, methylsulfonic acid, trifluoromethanesulfonic acid, trifluoroacetic acid; As preferably, used catalyst is one or more in sulfuric acid, hydrochloric acid, Phenylsulfonic acid, trifluoromethanesulfonic acid, trifluoroacetic acid; As most preferably, used catalyst is trifluoromethanesulfonic acid.
End-capping reagent is hexamethyldisiloxane or 1,1,3,3-tetramethyl disiloxane.
End-capping reagent consumption is the 0.1%-10% of the total amount of substance of monomer, and catalyst levels is the 0.1%-5% of monomer total mass.Monomer refers to D
m me, Phand D
n h(n=3,4,5).
D
m me, Phand D
n hthe mass percent scope of (n=3,4,5) is 94: 6-70: 30, and in product methyl and phenyl hydrogen-containing silicon oil, the mass percentage of hydrogen is 0.1%-0.5%.
The present invention adopts strong acid catalyst methyl phenyl ring siloxane and the reaction of methylhydracyclosiloxane ring-opening copolymerization to prepare the method for phenyl hydrogen-containing silicon oil of high refractive index, high transmission rate, compared with prior art, beneficial effect is: without the need to solvent, without the need to washing, technique is simple, reproducible.Other ingredient compatibilitys that obtained methyl and phenyl hydrogen-containing silicon oil rolls over packaging plastic with height are good, refractive index is between 1.49-1.53, containing hydrogen number between 0.1-0.5%, be suitable as the linking agent of LED encapsulation material, can be used as the anti-yellowing change agent of mixed milling type silicon rubber in addition, also can be used as the preparation that raw material carries out other high refractive index modified silicon oils.
Embodiment
Embodiment 1: by 147.8g methyl phenyl ring siloxane D
m me, Ph(m=3,4,5) dewater 0.5h under 50 DEG C/-0.1MPa, then adds through the dried D of Calcium Chloride Powder Anhydrous
n h(n=3,4,5) 36g, hexamethyldisiloxane 16.2g, 10g98% sulfuric acid, in 40 DEG C of balanced reaction 5h, then add appropriate NaHCO
3neutralization, after system neutrality, filter, clear liquid removes low molecular compound in 130 DEG C/-0.1MPa, is then cooled to room temperature, obtains water white liquid.N after testing
d 25=1.5086, H% (mass percent)=0.29%.
Embodiment 2: by 147.8g methyl phenyl ring siloxane D
m me, Ph(m=3,4,5) dewater 0.5h under 50 DEG C/-0.1MPa, then adds through the dried D of Calcium Chloride Powder Anhydrous
n h(n=3,4,5) 36g, hexamethyldisiloxane 16.2g, 10g98% sulfuric acid, in 50 DEG C of balanced reaction 3h, then add appropriate NaHCO
3neutralization, after system neutrality, filter, clear liquid removes low molecular compound in 130 DEG C/-0.1MPa, is then cooled to room temperature, obtains water white liquid.N after testing
d 25=1.5082, H% (mass percent)=0.3%.
Embodiment 3: by 138.8g methyl phenyl ring siloxane D
m me, Ph(m=3,4,5) dewater 0.5h under 50 DEG C/-0.1MPa, then adds through the dried D of Calcium Chloride Powder Anhydrous
n h(n=3,4,5) 36g, 1,1,3,3-tetramethyl disiloxane 25.2g, 10g98% sulfuric acid, in 50 DEG C of balanced reaction 5h, then adds appropriate NaHCO
3neutralization, after system neutrality, filter, clear liquid removes low molecular compound in 130 DEG C/-0.1MPa, is then cooled to room temperature, obtains water white liquid.N after testing
d 25=1.4954, H% (mass percent)=0.44%.
Embodiment 4: by 138.8g methyl phenyl ring siloxane D
m me, Ph(m=3,4,5) dewater 0.5h under 50 DEG C/-0.1MPa, then adds through the dried D of Calcium Chloride Powder Anhydrous
n h(n=3,4,5) 36g, 1,1,3,3-tetramethyl disiloxane 25.2g, 10g98% sulfuric acid, in 60 DEG C of balanced reaction 3h, then adds appropriate NaHCO
3neutralization, after system neutrality, filter, clear liquid removes low molecular compound in 130 DEG C/-0.1MPa, is then cooled to room temperature, obtains water white liquid.N after testing
d 25=1.4958, H% (mass percent)=0.42%.
Embodiment 5: by 277.6g methyl phenyl ring siloxane D
m me, Ph(m=3,4,5) dewater 0.5h under 50 DEG C/-0.1MPa, then adds through the dried D of Calcium Chloride Powder Anhydrous
n h(n=3,4,5) 72g, 1,1,3,3-tetramethyl disiloxane 50.4g, 4g trifluoromethanesulfonic acid, in 50 DEG C of balanced reaction 5h, then adds appropriate NaHCO
3neutralization, after system neutrality, filter, clear liquid removes low molecular compound in 150 DEG C/-0.1MPa, is then cooled to room temperature, obtains water white liquid.N after testing
d 25=1.5021, H% (mass percent)=0.41%.
Embodiment 6: by 277.6g methyl phenyl ring siloxane D
m me, Ph(m=3,4,5) dewater 0.5h under 50 DEG C/-0.1MPa, then adds through the dried D of Calcium Chloride Powder Anhydrous
n h(n=3,4,5) 72g, 1,1,3,3-tetramethyl disiloxane 50.4g, 4g trifluoromethanesulfonic acid, in 60 DEG C of balanced reaction 5h, then adds appropriate NaHCO
3neutralization, after system neutrality, filter, clear liquid removes low molecular compound in 150 DEG C/-0.1MPa, is then cooled to room temperature, obtains water white liquid.N after testing
d 25=1.5026, H% (mass percent)=0.4%.
Embodiment 7: by 136.22g methyl phenyl ring siloxane D
m me, Ph(m=3,4,5) dewater 0.5h under 50 DEG C/-0.1MPa, and then add through dried 1,1,3, the 3-tetramethyl disiloxane 12.6g of Calcium Chloride Powder Anhydrous, 1.49g trifluoromethanesulfonic acid, in 50 DEG C of balanced reaction 5h, then adds appropriate NaHCO
3neutralization, after system neutrality, filter, clear liquid removes low molecular compound in 150 DEG C/-0.1MPa, is then cooled to room temperature, obtains water white liquid.N after testing
d 25=1.5299, H% (mass percent)=0.15%.
Embodiment 8: by 136.22g methyl phenyl ring siloxane D
m me, Ph(m=3,4,5) dewater 0.5h under 50 DEG C/-0.1MPa, and then add through dried 1,1,3, the 3-tetramethyl disiloxane 12.6g of Calcium Chloride Powder Anhydrous, 1.49g trifluoromethanesulfonic acid, in 70 DEG C of balanced reaction 3h, then adds appropriate NaHCO
3neutralization, after system neutrality, filter, clear liquid removes low molecular compound in 150 DEG C/-0.1MPa, is then cooled to room temperature, obtains water white liquid.N after testing
d 25=1.5302, H% (mass percent)=0.12%.
Above embodiment is only the present invention's preferably embodiment, and its explanation is only applicable to the principle helping to understand the embodiment of the present invention, and basis of the present invention can be made some amendments to it or improve, and this will be apparent to those skilled in the art.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, all belong to the scope of protection of present invention.
Claims (7)
1. prepare a method for methyl and phenyl hydrogen-containing silicon oil, it is characterized in that, comprising: 1) by methyl phenyl ring siloxane D
m me, Ph(m=3,4,5) decompression dehydration, then adds methylhydracyclosiloxane D
n h(n=3,4,5), end-capping reagent, under the catalysis of strong acid catalyst, carry out ring-opening copolymerization reaction, reaction expression is as follows:
Wherein D
m me, Ph, D
n hchemical structural formula is as follows:
2) be polymerized complete, add sodium bicarbonate neutralization, filter, by the clear liquid removed under reduced pressure low molecule of gained, be then cooled to room temperature, obtain water white liquid, be methyl and phenyl hydrogen-containing silicon oil.
2. preparation method as claimed in claim 1, it is characterized in that polymeric reaction temperature controls as 30-80 DEG C, polymerization time is 1-6h.
3. preparation method as claimed in claim 2, it is characterized in that polymeric reaction temperature controls as 50-60 DEG C, polymerization time is 3-5h.
4. preparation method as claimed in claim 1, is characterized in that described strong acid catalyst is one or more in sulfuric acid, hydrochloric acid, nitric acid, perchloric acid, Phenylsulfonic acid, p-methyl benzenesulfonic acid, methylsulfonic acid, trifluoromethanesulfonic acid, trifluoroacetic acid; As preferably, used catalyst is one or more in sulfuric acid, hydrochloric acid, Phenylsulfonic acid, trifluoromethanesulfonic acid, trifluoroacetic acid; As most preferably, used catalyst is trifluoromethanesulfonic acid.
5. method as claimed in claim 1, it is characterized in that end-capping reagent consumption is the 0.1%-10% of the total amount of substance of monomer, catalyst levels is the 0.1%-5% of monomer total mass.
6. preparation method as claimed in claim 1, is characterized in that described end-capping reagent is hexamethyldisiloxane or 1,1,3,3-tetramethyl disiloxane.
7. method as claimed in claim 1, is characterized in that D
m me, Phand D
n hthe mass percent of (n=3,4,5) is 94: 6-70: 30.
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| CN105199105A (en) * | 2015-09-29 | 2015-12-30 | 广州有色金属研究院 | Method for preparing phenyl silicone oil with fluorine |
| CN105820341A (en) * | 2016-04-18 | 2016-08-03 | 广州市银讯光电科技有限公司 | Silicone crosslinking agent for packaging LED chips and preparation method of silicone crosslinking agent |
| WO2023035283A1 (en) * | 2021-09-10 | 2023-03-16 | 山东大学 | Ultra-low viscosity liquid silicone rubber, cross-linking agent theerefo, and preparation method therefor |
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Application publication date: 20150603 |