CN104140533A - Vinyl-containing phenyl hydro silicone resin and preparation method thereof - Google Patents
Vinyl-containing phenyl hydro silicone resin and preparation method thereof Download PDFInfo
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- CN104140533A CN104140533A CN201310167027.5A CN201310167027A CN104140533A CN 104140533 A CN104140533 A CN 104140533A CN 201310167027 A CN201310167027 A CN 201310167027A CN 104140533 A CN104140533 A CN 104140533A
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Abstract
The invention relates to organic silicon resin, especially relates to vinyl-containing phenyl hydro silicone resin which has high refractive index and high transparency and is used for high power LED packaging and a preparation method thereof. The vinyl-containing phenyl hydro silicone resin is prepared from monomeric silane, a hydro capping agent and a vinyl capping agent by hydrolysis and polycondensation reaction and after-treatment, the prepared vinyl-containing phenyl hydro silicone resin has high refractive index and high transparency, and has adjustable viscosity, phenyl, vinyl content and hydro contents and other characteristics, after addition curing of the vinyl-containing phenyl hydro silicone resin and vinyl resin, a prepared LED packaging material is high in hardness, less in internal stress, and large in tear strength. The vinyl-containing phenyl hydro silicone resin used for high power LED packaging has the following structure shown in the specification.
Description
Technical field
The present invention relates to silicone resin, relate in particular to a kind of phenyl-based hydrogen-based silicone resin containing vinyl of using for high-power LED encapsulation with high refractive index, high transmission rate and preparation method thereof.
Background technology
LED is the abbreviation of light emitting diode, electric energy can be converted into luminous energy, has the features such as energy-saving and environmental protection, safety, life-span length, brightness and the easy adjusting of illumination effect; These features of LED have met current people under energy dilemma and have possessed for prepared product in pursuing environmental protection the standard of carbon reduction; therefore LED has obtained increasing concern in recent years; also obtained development at full speed; become the 4th generation light source, be expected to extensively promoted and use.
Packaged material plays protection and supporting role to LED, can also adjust light effect, can directly affect use properties and the life-span of LED.In fact, the performance of LED packaging depends on chip in 50% degree, and 50% depends on packaging process and packaged material.Therefore, high performance packaged material is most important to the performance impact of LED, therefore becomes the focus of scientific research personnel's research in recent years.
What traditional packaged material used is epoxy resin, but epoxy resin has the shortcomings such as large, the easy xanthochromia of internal stress, resistance toheat and ultra-violet resistance can differ from, and therefore along with the raising of LED power, epoxy resin can not meet the application as packaged material.In contrast, organosilicon material has that internal stress is little, transmittance is high, resistance toheat and ultra-violet resistance can wait well advantage, just becomes main packaged material at substituted epoxy resin.
To organosilyl search time early, existing ripe organosilicon product is put on market now, and domestic market is also almost captured by these overseas enterprises completely in overseas enterprise.In recent years, domestic a lot of colleges and universities and enterprise have also launched similar research, and apply for patent, but the disclosed organosilyl structure design of these patents is all hydrogeneous base only, the product hardness obtaining after the organosilicon product of this hydrogeneous base and vinyl component addition curing is low, and intensity difference.
Summary of the invention
The object of this invention is to provide a kind of phenyl-based hydrogen-based silicone resin containing vinyl of using for high-power LED encapsulation with high refractive index, high transmission rate.
A further object of the present invention is to provide a kind of preparation method of the phenyl-based hydrogen-based silicone resin containing vinyl of using for high-power LED encapsulation.
Phenyl-based hydrogen-based silicone resin containing vinyl of the present invention has that specific refractory power is high, transmittance is high, there is all features such as adjustable of viscosity, phenyl content, contents of ethylene and hydrogen base content simultaneously, of the present invention containing after the phenyl-based hydrogen-based silicone resin and Vinylite addition curing of vinyl, the LED packaged material hardness obtaining is large, internal stress is little, and tearing toughness is large.
Phenyl-based hydrogen-based silicone resin containing vinyl of the present invention has following structure:
R in formula
1, R
2, R
3be independently CH
3or C
6h
5; The shared mole number of each siloxane unit when whole siloxane units that m, n represent respectively to form silicone resin are 1mol, and m+n=1; Vi is vinyl.
The preparation method of the phenyl-based hydrogen-based silicone resin containing vinyl of the present invention comprises hydrolysis reaction, polycondensation and aftertreatment, and its preparation method comprises the following steps:
(1) by the mixture of water and catalyzer, under being 0～40 DEG C and violent stirring, temperature is added drop-wise in the mixture of monomeric silanes and toluene solvant, after dropwising, obtaining reaction system, is the reaction (time of selective hydrolysis reaction is 1～16 hour) that is hydrolyzed at 50～100 DEG C in temperature;
(2) under agitation in the reaction solution obtaining after step (1) hydrolysis reaction completes, add hydrogen base end-capping reagent, ethenyl blocking agent and toluene solvant, be at 50～100 DEG C, to carry out polycondensation 2～8 hours in temperature, after completing, polycondensation stops heating, wherein: ethenyl blocking agent: the mol ratio of hydrogen base end-capping reagent is 1:1～1:100; And hydrogen base end-capping reagent and ethenyl blocking agent add total amount be monomeric silanes in step (1) reaction system quality percentage composition 5%～80%;
(3) in the reaction solution obtaining after step (2) polycondensation completes, add water and be uniformly mixed, then stratification, gets organic layer, and water cleans organic layer repeatedly to neutral, revolve to steam and remove lower-molecular substance, obtain the phenyl-based hydrogen-based silicone resin containing vinyl.
The mass concentration of the catalyzer in the reaction system described in step (1) is 0.1%～15%.
Described catalyzer is selected from the one in sulfuric acid, phosphoric acid, hydrochloric acid, trifluoromethayl sulfonic acid, acidic cation-exchange resin.
Described acidic cation-exchange resin is selected from phenylethylene resin series.
The mass concentration of the monomeric silanes in the reaction system described in step (1) is 40%～90%.
Described monomeric silanes is selected from one or more in phenyltrimethoxysila,e, aminomethyl phenyl dimethoxy silane, dimethoxydiphenylsilane, phenyl-trichloro-silicane, dichloromethyl phenylsilane, diphenyl dichlorosilane; Or be selected from several in phenyltrimethoxysila,e, aminomethyl phenyl dimethoxy silane, dimethyldimethoxysil,ne, methyltrimethoxy silane, dimethoxydiphenylsilane, phenyl-trichloro-silicane, dichloromethyl phenylsilane, dimethyldichlorosilane(DMCS), METHYL TRICHLORO SILANE, diphenyl dichlorosilane, and in selected monomeric silanes, to have at least a kind of be the monomeric silanes that contains phenyl.
Described hydrogen base end-capping reagent is tetramethyl disiloxane (H-MM); Or the mixture of tetramethyl disiloxane (H-MM) and hexamethyldisiloxane (MM), and in mixture, the content of tetramethyl disiloxane is greater than 0.
Described ethenyl blocking agent is 1,3-divinyl-tetramethyl disiloxane (Vi-MM); Or the mixture of 1,3-divinyl-tetramethyl disiloxane (Vi-MM) and hexamethyldisiloxane (MM), and in mixture 1, the content of 3-divinyl-tetramethyl disiloxane is greater than 0.
The phenyl-based hydrogen-based silicone resin raw material used containing vinyl of using for high-power LED encapsulation of the present invention is easy to get, and preparation method is easy, and every batch of phenyl-based hydrogen-based silicone resin containing vinyl preparing all has good stability and transmittance high; In addition, in the molecule of the described phenyl-based hydrogen-based silicone resin containing vinyl, contain vinyl and hydrogen base simultaneously, molecule inner injection can occur and close; Phenyl-based hydrogen-based silicone resin containing vinyl of the present invention with Vinylite addition curing after, the LED packaged material hardness obtaining is large, internal stress is little, tearing toughness is large, is suitable as very much the packaged material of LED.
Brief description of the drawings
Fig. 1. the nuclear magnetic spectrogram of the embodiment of the present invention 1 products therefrom.
Fig. 2. the nuclear magnetic spectrogram of the embodiment of the present invention 2 products therefroms.
Fig. 3. the nuclear magnetic spectrogram of the embodiment of the present invention 3 products therefroms.
Embodiment
Below by specific embodiment, the present invention is elaborated, but the present invention is not limited to following embodiment.
Embodiment 1
In the there-necked flask of 250ml, add diphenyl dichlorosilane 15.62g, phenyl-trichloro-silicane 28.46g and toluene 5g to stir, the temperature of controlling in there-necked flask is 0～5 DEG C, under agitation drip 8.07g and contain the deionized water that mass concentration is 5% hydrochloric acid, after being added dropwise to complete, temperature is risen to 50 DEG C of reactions 16 hours that are hydrolyzed; At the H-MM of Vi-MM, 4.44g and the toluene of 35g that continue to add under stirring 2.16g, be then at 50 DEG C, to proceed polycondensation 4 hours in temperature; After being cooled to room temperature, add deionized water, after stirring, leave standstill branch vibration layer, get organic layer and wash 2～5 times to neutral with deionized water, finally proceed in single port bottle and revolve and steam except desolventizing, obtain achromaticity and clarification transparent there is aforementioned structure (wherein R
1, R
2and R
3be C
6h
5and m=0.32, n=0.68) LED phenyl-based hydrogen-based silicone resin for encapsulating 25.16g, should see Fig. 1 containing the nuclear magnetic spectrogram of the phenyl-based hydrogen-based silicone resin of vinyl, viscosity, refractive index and transmittance data are in table 1, should be greater than ShoreA80 containing the hardness after phenyl-based hydrogen-based silicone resin and the Vinylite addition curing of vinyl, and be difficult for tearing.
Embodiment 2
In the there-necked flask of 250ml, add phenyltrimethoxysila,e 20.16g, aminomethyl phenyl dimethoxy silane 1.92g, diphenyl dichlorosilane 6.84g and toluene 5g to stir, the temperature of controlling in there-necked flask is 10～20 DEG C, under agitation drip 5.07g and contain the deionized water that mass concentration is 0.1% hydrochloric acid, after being added dropwise to complete, temperature is risen to 90 DEG C of reactions 1 hour that are hydrolyzed; At the H-MM of Vi-MM, 2.55g and the toluene of 35g that continue to add under stirring 2.72g, be then at 90 DEG C, to proceed polycondensation 4 hours in temperature; After being cooled to room temperature, add deionized water, after stirring, leave standstill branch vibration layer, get organic layer and wash 2～5 times to neutral with deionized water, finally proceed in single port bottle and revolve and steam except desolventizing, obtain achromaticity and clarification transparent there is aforementioned structure (wherein R
1and R
2for C
6h
5, R
3for C
6h
5and CH
3and m=0.73, n=0.27) LED phenyl-based hydrogen-based silicone resin for encapsulating 20.71g, should see Fig. 2 containing the nuclear magnetic spectrogram of the phenyl-based hydrogen-based silicone resin of vinyl, viscosity, refractive index and transmittance data are in table 1, should be greater than ShoreA85 containing the hardness after phenyl-based hydrogen-based silicone resin and the Vinylite addition curing of vinyl, and be difficult for tearing.
Embodiment 3
In the there-necked flask of 250ml, add methyltrimethoxy silane 9.31g, phenyltrimethoxysila,e 12.16g, aminomethyl phenyl dimethoxy silane 14.52g and toluene 5g to stir, the temperature of controlling in there-necked flask is 35～40 DEG C, under agitation drip 5.07g and contain the deionized water that mass concentration is 5% trifluoromethayl sulfonic acid, after being added dropwise to complete, temperature is risen to 60 DEG C of reactions 6 hours that are hydrolyzed; At the H-MM of Vi-MM, 4.63g and the toluene of 35g that continue to add under stirring 3.82g, be then at 60 DEG C, to proceed polycondensation 6 hours in temperature; After being cooled to room temperature, add deionized water, after stirring, leave standstill branch vibration layer, get organic layer and wash 2～5 times to neutral with deionized water, finally proceed in single port bottle and revolve and steam except desolventizing, obtain achromaticity and clarification transparent there is aforementioned structure (wherein R
1for C
6h
5and CH
3, R
2for C
6h
5, R
3for CH
3and m=0.0.62, n=0.38) LED phenyl-based hydrogen-based silicone resin for encapsulating 20.63g, should see Fig. 3 containing the nuclear magnetic spectrogram of the phenyl-based hydrogen-based silicone resin of vinyl, viscosity, refractive index and transmittance data are in table 1, should be greater than ShoreA80 containing the hardness after phenyl-based hydrogen-based silicone resin and the Vinylite addition curing of vinyl, and be difficult for tearing.
Table 1
| ? | Viscosity (cps) | Refractive index | Transmittance/%, 400nm place, thickness is 1cm |
| Embodiment 1 | 1721 | 1.5425 | 95.62 |
| Embodiment 2 | 3492 | 1.535 | 94.38 |
| Embodiment 3 | 1250 | 1.5270 | 96.72 |
The performance data of above-described embodiment all adopts the testing method in industry to test, the test of the transmitance of light adopts T6 new millennium ultraviolet-visible pectrophotometer (Beijing Puxi General Instrument Co., Ltd's production), viscosity test adopts the digital viscometer of DV-79 (Shanghai Guang Run intelligence Science and Technology Ltd. produces), refractive index test adopts 2WA-J type Abbe refractometer (Shanghai Optical Instruments Factory), and hardness test adopts LX-A type Shore durometer (China's silver is produced).
Claims (10)
1. containing a phenyl-based hydrogen-based silicone resin for vinyl, it is characterized in that: the described phenyl-based hydrogen-based silicone resin containing vinyl has following structure:
R in formula
1, R
2, R
3be independently CH
3or C
6h
5; The shared mole number of each siloxane unit when whole siloxane units that m, n represent respectively to form silicone resin are 1mol, and m+n=1; Vi is vinyl.
2. a preparation method for the phenyl-based hydrogen-based silicone resin containing vinyl according to claim 1, is characterized in that, described preparation method comprises the following steps:
(1) by the mixture of water and catalyzer, temperature be 0～40 DEG C and stir under be added drop-wise in the mixture of monomeric silanes and toluene solvant, after dropwising, obtain reaction system, be the reaction that is hydrolyzed at 50～100 DEG C in temperature;
(2) under agitation in the reaction solution obtaining after step (1) hydrolysis reaction completes, add hydrogen base end-capping reagent, ethenyl blocking agent and toluene solvant, be at 50～100 DEG C, to carry out polycondensation 2～8 hours in temperature, after completing, polycondensation stops heating, wherein: ethenyl blocking agent: the mol ratio of hydrogen base end-capping reagent is 1:1～1:100; And hydrogen base end-capping reagent and ethenyl blocking agent add total amount be monomeric silanes in step (1) reaction system quality percentage composition 5%～80%;
(3) in the reaction solution obtaining after step (2) polycondensation completes, add water and be uniformly mixed, then stratification, gets organic layer, and water cleans organic layer repeatedly to neutral, revolve to steam and remove lower-molecular substance, obtain the phenyl-based hydrogen-based silicone resin containing vinyl.
3. preparation method according to claim 2, is characterized in that: described is that be hydrolyzed at 50～100 DEG C time of reaction is 1～16 hour in temperature.
4. preparation method according to claim 2, is characterized in that: the mass concentration of the catalyzer in the reaction system described in step (1) is 0.1%～15%.
5. according to the preparation method described in claim 2 or 4, it is characterized in that: described catalyzer is selected from the one in sulfuric acid, phosphoric acid, hydrochloric acid, trifluoromethayl sulfonic acid, acidic cation-exchange resin.
6. preparation method according to claim 5, is characterized in that: described acidic cation-exchange resin is selected from phenylethylene resin series.
7. preparation method according to claim 2, is characterized in that: the mass concentration of the monomeric silanes in the reaction system described in step (1) is 40%～90%.
8. according to the preparation method described in claim 2 or 7, it is characterized in that: described monomeric silanes is selected from one or more in phenyltrimethoxysila,e, aminomethyl phenyl dimethoxy silane, dimethoxydiphenylsilane, phenyl-trichloro-silicane, dichloromethyl phenylsilane, diphenyl dichlorosilane; Or be selected from several in phenyltrimethoxysila,e, aminomethyl phenyl dimethoxy silane, dimethyldimethoxysil,ne, methyltrimethoxy silane, dimethoxydiphenylsilane, phenyl-trichloro-silicane, dichloromethyl phenylsilane, dimethyldichlorosilane(DMCS), METHYL TRICHLORO SILANE, diphenyl dichlorosilane, and in selected monomeric silanes, to have at least a kind of be the monomeric silanes that contains phenyl.
9. preparation method according to claim 2, is characterized in that: described hydrogen base end-capping reagent is tetramethyl disiloxane; Or the mixture of tetramethyl disiloxane and hexamethyldisiloxane, and in mixture, the content of tetramethyl disiloxane is greater than 0.
10. preparation method according to claim 2, is characterized in that: described ethenyl blocking agent is 1,3-divinyl-tetramethyl disiloxane; Or the mixture of 1,3-divinyl-tetramethyl disiloxane and hexamethyldisiloxane, and in mixture 1, the content of 3-divinyl-tetramethyl disiloxane is greater than 0.
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| CN201310167027.5A CN104140533A (en) | 2013-05-08 | 2013-05-08 | Vinyl-containing phenyl hydro silicone resin and preparation method thereof |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106221237A (en) * | 2016-07-27 | 2016-12-14 | 瑞金市瑞谷科技发展有限公司 | A kind of LED encapsulation organic silica gel and preparation method thereof |
| CN108203545A (en) * | 2016-12-16 | 2018-06-26 | 北京科化新材料科技有限公司 | Solid-state silicon resin composition and its preparation method and application and optoelectronic part case |
| CN108473768A (en) * | 2015-12-30 | 2018-08-31 | 美国圣戈班性能塑料公司 | Radiation-curable product and its preparation and application |
| CN109722218A (en) * | 2018-12-25 | 2019-05-07 | 烟台德邦科技有限公司 | A kind of electrolyte resistance sealant and preparation method thereof |
| CN109796931A (en) * | 2017-11-16 | 2019-05-24 | 北京科化新材料科技有限公司 | Silicon resin composition and its application and LED encapsulation material |
| CN111057240A (en) * | 2019-11-28 | 2020-04-24 | 湖北新四海化工股份有限公司 | Method for preparing resin from phenyl alkoxy silane high-boiling residues |
| CN112694865A (en) * | 2020-12-18 | 2021-04-23 | 广东普赛达密封粘胶有限公司 | Single-component thermosetting organic silicon adhesive for adhering electric kettle and preparation method thereof |
| CN114163613A (en) * | 2020-09-10 | 2022-03-11 | 北京科化新材料科技有限公司 | Packaging material and preparation method and application thereof |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108473768A (en) * | 2015-12-30 | 2018-08-31 | 美国圣戈班性能塑料公司 | Radiation-curable product and its preparation and application |
| US11267944B2 (en) | 2015-12-30 | 2022-03-08 | Saint-Gobain Performance Plastics Corporation | Radiation curable article and method for making and using same |
| CN106221237A (en) * | 2016-07-27 | 2016-12-14 | 瑞金市瑞谷科技发展有限公司 | A kind of LED encapsulation organic silica gel and preparation method thereof |
| CN108203545A (en) * | 2016-12-16 | 2018-06-26 | 北京科化新材料科技有限公司 | Solid-state silicon resin composition and its preparation method and application and optoelectronic part case |
| CN109796931A (en) * | 2017-11-16 | 2019-05-24 | 北京科化新材料科技有限公司 | Silicon resin composition and its application and LED encapsulation material |
| CN109722218A (en) * | 2018-12-25 | 2019-05-07 | 烟台德邦科技有限公司 | A kind of electrolyte resistance sealant and preparation method thereof |
| CN109722218B (en) * | 2018-12-25 | 2021-05-04 | 烟台德邦科技股份有限公司 | Electrolyte-resistant sealant and preparation method thereof |
| CN111057240A (en) * | 2019-11-28 | 2020-04-24 | 湖北新四海化工股份有限公司 | Method for preparing resin from phenyl alkoxy silane high-boiling residues |
| CN114163613A (en) * | 2020-09-10 | 2022-03-11 | 北京科化新材料科技有限公司 | Packaging material and preparation method and application thereof |
| CN114163613B (en) * | 2020-09-10 | 2024-03-12 | 北京科化新材料科技有限公司 | Packaging material, preparation method and application thereof |
| CN112694865A (en) * | 2020-12-18 | 2021-04-23 | 广东普赛达密封粘胶有限公司 | Single-component thermosetting organic silicon adhesive for adhering electric kettle and preparation method thereof |
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