CN104292465A - Epoxy-modified phenyl vinyl silicon resin and preparation method thereof - Google Patents
Epoxy-modified phenyl vinyl silicon resin and preparation method thereof Download PDFInfo
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- CN104292465A CN104292465A CN201410550515.9A CN201410550515A CN104292465A CN 104292465 A CN104292465 A CN 104292465A CN 201410550515 A CN201410550515 A CN 201410550515A CN 104292465 A CN104292465 A CN 104292465A
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Abstract
The invention discloses an epoxy-modified phenyl vinyl silicon resin and a preparation method thereof. The epoxy-modified phenyl vinyl silicon resin comprises an epoxy group-containing monomer, one or more phenyl-containing organosilicon monomers, a methyl-containing organosilicon monomer, a vinyl end-capping reagent and a vinyl-containing monomer; in the presence of a catalyst, the epoxy-modified phenyl vinyl silicon resin is obtained by virtue of the steps of medium-temperature hydrolysis, condensation, and solvent removal after filtering. The epoxy-modified phenyl vinyl silicon resin is usable as an organosilicon modified material high-molecular basic polymer for high-power LED packaging, and the bonding strength of a cured material to a substrate can be greatly improved, and furthermore, the service life of an LED lamp bead in severe environment can be further prolonged.
Description
Technical field
The present invention relates to a kind of preparation method of epoxide modified phenyl vinyl polysiloxane, particularly relate to a kind of epoxide modified phenyl vinyl polysiloxane and preparation method thereof.
Background technology
Photodiode has the advantages such as energy-saving and environmental protection, safety, life-span length, through the development of decades, is widely applied to backlight, area source, display screen, interior lighting, the aspects such as automotive lighting, is expected to the forth generation light source replacing traditional lighting.
The packaged material of current common LED mainly epoxy resin, but traditional epoxy resin is aging poor at ultraviolet resistance, inevitably there is xanthochromia in long-time use, transmittance is caused to be deteriorated, reduce the luminosity of LED chip, the thermal resistance of epoxy resin is up to 250 ~ 300 DEG C/W in addition, thus cause chip cooling bad, temperature rises rapidly, thus exacerbate the aging of device, the stress that even can produce because of rapid expanded by heating causes open circuit and lost efficacy, therefore, along with development and the lifting of LED technology, also more and more higher to the requirement of packaged material, epoxy resin can not meet the encapsulation requirement of LED completely.
Organosilicon material has high temperature resistant, aging, ultraviolet resistance, the advantages such as radiation hardness, it is desirable LED encapsulation material, but simple add-on type transparent liquid organosilicon material does not have the binding function to base material, thus cause open circuit under causing cold and hot contraction or external force situation from base material from stripping and lost efficacy, need to add epoxies coupling agent in addition and improve adhesive effect, but simply add epoxies coupling agent, consistency and the easy deliquescent behaviours of coupling agent, system is easily made to turn white, the moisture absorption, deliquescence causes the colloid after solidifying to turn white, embrittlement, thus flaw or transmittance reduce to cause the LED lamp bead after encapsulating to occur, and the material that the present invention relates to is that epoxide group is introduced in organosilicon systems, the consistence of system can be accomplished, consistency and high-clarity, thus modification phenyl vinyl polysiloxane is gone also can greatly can to improve bonding force to ground outward keeping silicone based advantage with epoxy.
Summary of the invention
Object of the present invention is just to provide a kind of epoxide modified phenyl vinyl polysiloxane and preparation method thereof to solve the problem.
The present invention is achieved through the following technical solutions above-mentioned purpose:
The general structure I of epoxide modified phenyl vinyl polysiloxane of the present invention is:
R
3MeSiO
0.5[SiO
2]
a[PhSiO
1.5]
b[R
1PhSiO]
c[R
2MeSiO]
dMeSiO
0.5R
3
In described I formula, R
1for-CH
3,-C
6h
5or-OCH
2cHOCH
2; R
2for-CH
3,-CH=CH
2,-C
6h
5or-OCH
2cHOCH
2; R
3for-CH
3,-CH=CH
2or-OCH
2cHOCH
2; A is between 0-4; B is between 1-20; C is between 0-12; D is between 0-8.
Further, the space structure of described epoxide modified phenyl vinyl polysiloxane molecule is dumbbell shaped, T-shaped or space multistory reticulated structure.
Further, described epoxide modified phenyl vinyl polysiloxane comprise containing epoxy group(ing) monomer, one or more containing phenyl organosilane monomer, methyl monomer, methyl vinyl monomer and closure agent at the aqueous solution of acidity, carried out cohydrolysis-condensation reaction, temperature is between 0-120 DEG C, react between 2-10 hour, neutralization &washing is to neutral after completion of the reaction, is filtered to clarification; Then intensification removed under reduced pressure low molecule, its vacuum tightness-0.096MPa, keeps 1-3 hour at temperature 120-170 DEG C, finally obtains epoxide modified phenyl vinyl polysiloxane.
Further, the alkoxy silane monomer of described four senses is selected from methyl silicate Si (OMe)
4or tetraethoxy Si (OEt)
4; Described trifunctional alkoxy silane monomer is selected from phenyltrimethoxysila,e PhSi (OMe)
3or phenyl triethoxysilane PhSi (OEt)
3; Described two functional alkoxysilanes monomers are selected from aminomethyl phenyl dimethoxysilane PhMe
3si (OMe)
2, aminomethyl phenyl diethoxy silane PhMe
3si (OEt)
2, dimethoxydiphenylsilane Ph
2si (OMe)
2, diphenyl diethoxy silane Ph
2si (OEt)
2, dimethyldimethoxysil,ne Me
2si (OMe)
2, dimethyldiethoxysilane Me
2si (OEt)
2in one or more; Described simple function alkoxy silane monomer is selected from methyl double-seal head (Me
3si)
2o, vinyl double-seal head (CH
2=CHMe
2si)
2o, vinyl list end socket CH
2=CHMe
2one or more in Si (OEt); Described epoxy based monomers is selected from R-GLYCIDOL CH
2oCHCH
2oH.
Further, according to different refractive index requirements, described refractive index is between 1.45-1.55, and in selected monomer, the mol ratio of phenyl and non-hydrolytic group is 0.15 ~ 0.6:1.
Further, the mol ratio of described epoxide group and described non-hydrolytic group is: 1 ~ 50:1000.
Further, according to molecular structure and molecular size, its mol ratio feeding intake selected monomer non-hydrolytic group and closure agent is: 10 ~ 1000:1, and the mole number of water is 1.5-2.5 times of the mole number of hydrolyzable functional group.
Beneficial effect of the present invention is:
Modified silicone resin prepared by the present invention is applicable to the organic-silicon-modified material polymer basis polymkeric substance being used as high power type LED industry, greatly can improve the bonding strength of cured article to base material, thus extend further LED lamp bead work-ing life in the presence of a harsh environment.
Embodiment
The invention will be further described below:
The general structure I of epoxide modified phenyl vinyl polysiloxane of the present invention is:
R
3MeSiO
0.5[SiO
2]
a[PhSiO
1.5]
b[R
1PhSiO]
c[R
2MeSiO]
dMeSiO
0.5R
3
In described I formula, R
1for-CH
3,-C
6h
5or-OCH
2cHOCH
2; R
2for-CH
3,-CH=CH
2,-C
6h
5or-OCH
2cHOCH
2; R
3for-CH
3,-CH=CH
2or-OCH
2cHOCH
2; A is between 0-4; B is between 1-20; C is between 0-12; D is between 0-8, the space structure of described epoxide modified phenyl vinyl polysiloxane molecule is dumbbell shaped, T-shaped or space multistory reticulated structure, described epoxide modified phenyl vinyl polysiloxane comprise containing epoxy group(ing) monomer, one or more containing phenyl organosilane monomer, methyl monomer, methyl vinyl monomer and closure agent at the aqueous solution of acidity, carried out cohydrolysis-condensation reaction, temperature is between 0-120 DEG C, react between 2-10 hour, neutralization &washing is to neutral after completion of the reaction, is filtered to clarification; Then intensification removed under reduced pressure low molecule, its vacuum tightness-0.096MPa, keeps 1-3 hour at temperature 120-170 DEG C, finally obtains epoxide modified phenyl vinyl polysiloxane, and the alkoxy silane monomer of described four senses is selected from methyl silicate Si (OMe)
4or tetraethoxy Si (OEt)
4; Described trifunctional alkoxy silane monomer is selected from phenyltrimethoxysila,e PhSi (OMe)
3or phenyl triethoxysilane PhSi (OEt)
3; Described two functional alkoxysilanes monomers are selected from aminomethyl phenyl dimethoxysilane PhMe
3si (OMe)
2, aminomethyl phenyl diethoxy silane PhMe
3si (OEt)
2, dimethoxydiphenylsilane Ph
2si (OMe)
2, diphenyl diethoxy silane Ph
2si (OEt)
2, dimethyldimethoxysil,ne Me
2si (OMe)
2, dimethyldiethoxysilane Me
2si (OEt)
2in one or more; Described simple function alkoxy silane monomer is selected from methyl double-seal head (Me
3si)
2o, vinyl double-seal head (CH
2=CHMe
2si)
2o, vinyl list end socket CH
2=CHMe
2one or more in Si (OEt); Described epoxy based monomers is selected from R-GLYCIDOL CH
2oCHCH
2oH, according to different refractive index requirements, described refractive index is between 1.45-1.55, in selected monomer, the mol ratio of phenyl and non-hydrolytic group is 0.15 ~ 0.6:1, the mol ratio of described epoxide group and described expense hydrolysising group is: 1 ~ 50:1000, according to molecular structure and molecular size, its mol ratio feeding intake selected monomer non-hydrolytic group and closure agent is: 10 ~ 1000:1, and the mole number of water is 1.5-2.5 times of the mole number of hydrolyzable functional group.
Embodiment one:
By 150g phenyltrimethoxysila,e, 40g vinyl double-seal head, 10g R-GLYCIDOL joins in the there-necked flask of 1000ml, stirring is warming up to 80 degree, instillation 5g concentration is 37% concentrated hydrochloric acid, 100g pure water mix acid liquor, drips in 60 minutes, keeps temperature reflux to react 5 hours, add toluene 250g and keep reaction 1 hour, stratification; Separately sour water layer, adds the stirring of 2g2% concentration hydrogen potassium oxide solution and is warming up to 120 degree, condensation reaction 4 hours; React complete and add Glacial acetic acid neutralization, filter out mechanical impurity, at 150-170 degree, under vacuum tightness-0.096MPa, remove low-boiling-point substance and solvent, obtain the epoxide modified phenyl vinyl polysiloxane of about 98g clear, refractive index (n
d 25) be 1.5285.
Embodiment two:
By 150g phenyltrimethoxysila,e, 50g dimethoxydiphenylsilane, 40g vinyl double-seal head, 10g R-GLYCIDOL joins in the there-necked flask of 1000ml, stirs and is warming up to 80 degree, and instillation 5g concentration is 37% concentrated hydrochloric acid, 120g pure water mix acid liquor, drip in 60 minutes, keep temperature reflux to react 5 hours, add toluene 300g and keep reaction 1 hour, stratification; Separately sour water layer, adds the stirring of 2g2% concentration hydrogen potassium oxide solution and is warming up to 120 degree, condensation reaction 4 hours; React complete and add Glacial acetic acid neutralization, filter out mechanical impurity, at 150-170 degree, under vacuum tightness-0.096MPa, remove low-boiling-point substance and solvent, obtain the epoxide modified phenyl vinyl polysiloxane of about 133g clear, refractive index (n
d 25) be 1.5427.
Embodiment three
By 150g phenyltrimethoxysila,e, 50g aminomethyl phenyl dimethoxysilane, 40g vinyl double-seal head, 10g R-GLYCIDOL joins in the there-necked flask of 1000ml, stirs and is warming up to 80 degree, and instillation 5g concentration is 37% concentrated hydrochloric acid, 120g pure water mix acid liquor, drip in 60 minutes, keep temperature reflux to react 5 hours, add toluene 300g and keep reaction 1 hour, stratification; Separately sour water layer, adds the stirring of 2g2% concentration hydrogen potassium oxide solution and is warming up to 120 degree, condensation reaction 4 hours; React complete and add Glacial acetic acid neutralization, filter out mechanical impurity, at 150-170 degree, under vacuum tightness-0.096MPa, remove low-boiling-point substance and solvent, obtain the epoxide modified phenyl vinyl polysiloxane of about 119g clear, refractive index (n
d 25) be 1.5343.
Embodiment four
By 150g phenyltrimethoxysila,e, 50g dimethyldimethoxysil,ne, 40g vinyl double-seal head, 10g R-GLYCIDOL joins in the there-necked flask of 1000ml, stirs and is warming up to 80 degree, and instillation 5g concentration is 37% concentrated hydrochloric acid, 120g pure water mix acid liquor, drip in 60 minutes, keep temperature reflux to react 5 hours, add toluene 300g and keep reaction 1 hour, stratification; Separately sour water layer, adds the stirring of 2g alkali lye 2% concentration hydrogen potassium oxide solution and is warming up to 120 degree, condensation reaction 4 hours; React complete and add Glacial acetic acid neutralization, filter out mechanical impurity, at 150-170 degree, under vacuum tightness-0.096MPa, remove low-boiling-point substance and solvent, obtain the epoxide modified phenyl vinyl polysiloxane of about 105g clear, refractive index (n
d 25) be 1.5011.
Embodiment five
By 150g phenyltrimethoxysila,e, 50g tetraethoxy, 40g vinyl double-seal head, 10g R-GLYCIDOL joins in the there-necked flask of 1000ml, stirs and is warming up to 80 degree, and instillation 5g concentration is 37% concentrated hydrochloric acid, 120g pure water mix acid liquor, drip in 60 minutes, keep temperature reflux to react 5 hours, add toluene 300g and keep reaction 1 hour, stratification; Separately sour water layer, adds the stirring of 2g alkali lye 2% concentration hydrogen potassium oxide solution and is warming up to 120 degree, condensation reaction 4 hours; React complete and add Glacial acetic acid neutralization, filter out mechanical impurity, at 150-170 degree, under vacuum tightness-0.096MPa, remove low-boiling-point substance and solvent, obtain the epoxide modified phenyl vinyl polysiloxane of about 100g clear, refractive index (n
d 25) be 1.4740.
Those skilled in the art do not depart from essence of the present invention and spirit, various deformation scheme can be had to realize the present invention, the foregoing is only the better feasible embodiment of the present invention, not thereby interest field of the present invention is limited to, the equivalent method change that all utilizations description of the present invention is done, is all contained within interest field of the present invention.
Claims (7)
1. epoxide modified phenyl vinyl polysiloxane and preparation method thereof, is characterized in that: the general structure I of described epoxide modified phenyl vinyl polysiloxane is:
R
3MeSiO
0.5[SiO
2]
a[PhSiO
1.5]
b[R
1PhSiO]
c[R
2MeSiO]
d?MeSiO
0.5R
3
In described I formula, R
1for-CH
3,-C
6h
5or-OCH
2cHOCH
2; R
2for-CH
3,-CH=CH
2,-C
6h
5or-OCH
2cHOCH
2; R
3for-CH
3,-CH=CH
2or-OCH
2cHOCH
2; A is between 0-4; B is between 1-20; C is between 0-12; D is between 0-8.
2. epoxide modified phenyl vinyl polysiloxane of one according to claim 1 and preparation method thereof, is characterized in that: the space structure of described epoxide modified phenyl vinyl polysiloxane molecule is dumbbell shaped, T-shaped or space multistory reticulated structure.
3. epoxide modified phenyl vinyl polysiloxane of one according to claim 1 and preparation method thereof, it is characterized in that: described epoxide modified phenyl vinyl polysiloxane comprise containing epoxy group(ing) monomer, one or more containing phenyl organosilane monomer, methyl monomer, methyl vinyl monomer and closure agent at the aqueous solution of acidity, carried out cohydrolysis-condensation reaction, temperature is between 0-120 DEG C, react between 2-10 hour, neutralization &washing is to neutral after completion of the reaction, is filtered to clarification; Then intensification removed under reduced pressure low molecule, its vacuum tightness-0.096MPa, keeps 1-3 hour at temperature 120-170 DEG C, finally obtains epoxide modified phenyl vinyl polysiloxane.
4. the preparation method of a kind of epoxide modified phenyl vinyl polysiloxane according to claim 1 and preparation method thereof, is characterized in that: the alkoxy silane monomer of described four senses is selected from methyl silicate Si (OMe)
4or tetraethoxy Si (OEt)
4; Described trifunctional alkoxy silane monomer is selected from phenyltrimethoxysila,e PhSi (OMe)
3or phenyl triethoxysilane PhSi (OEt)
3; Described two functional alkoxysilanes monomers are selected from aminomethyl phenyl dimethoxysilane PhMe
3si (OMe)
2, aminomethyl phenyl diethoxy silane PhMe
3si (OEt)
2, dimethoxydiphenylsilane Ph
2si (OMe)
2, diphenyl diethoxy silane Ph
2si (OEt)
2, dimethyldimethoxysil,ne Me
2si (OMe)
2, dimethyldiethoxysilane Me
2si (OEt)
2in one or more; Described simple function alkoxy silane monomer is selected from methyl double-seal head (Me
3si)
2o, vinyl double-seal head (CH
2=CHMe
2si)
2o, vinyl list end socket CH
2=CHMe
2one or more in Si (OEt); Described epoxy based monomers is selected from R-GLYCIDOL CH
2oCHCH
2oH.
5. the preparation method of a kind of epoxide modified phenyl vinyl polysiloxane according to claim 1-4 and preparation method thereof, it is characterized in that: according to different refractive index requirements, described refractive index is between 1.45-1.55, and in selected monomer, the mol ratio of phenyl and non-hydrolytic group is 0.15 ~ 0.6:1.
6. the preparation method of a kind of epoxide modified phenyl vinyl polysiloxane according to claim 5 and preparation method thereof, is characterized in that: the mol ratio of described epoxide group and described non-hydrolytic group is: 1 ~ 50:1000.
7. the preparation method of a kind of epoxide modified phenyl vinyl polysiloxane according to claim 6 and preparation method thereof, it is characterized in that: according to molecular structure and molecular size, its mol ratio feeding intake selected monomer non-hydrolytic group and closure agent is: 10 ~ 1000:1, and the mole number of water is 1.5-2.5 times of the mole number of hydrolyzable functional group.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109762167A (en) * | 2018-12-14 | 2019-05-17 | 中国科学院深圳先进技术研究院 | A kind of LED small-size chips heat conductive insulating die bond material and preparation method thereof |
| CN110903808A (en) * | 2019-11-07 | 2020-03-24 | 烟台德邦科技有限公司 | Epoxy-modified high-refractive-index LED packaging silica gel and preparation method thereof |
| CN111004605A (en) * | 2019-12-21 | 2020-04-14 | 东莞市贝特利新材料有限公司 | Self-adhesive organic silicon liquid silicone rubber for bonding glass substrate and forming process thereof |
| CN114752345A (en) * | 2022-03-09 | 2022-07-15 | 苏州艾迪亨斯胶粘技术有限公司 | Bi-component self-adhesive liquid silicone rubber and preparation method thereof |
| CN117467404A (en) * | 2023-12-25 | 2024-01-30 | 拓迪化学(上海)股份有限公司 | Double-component addition type organic silicon adhesive as well as preparation method and application thereof |
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| CN103012798A (en) * | 2012-11-23 | 2013-04-03 | 广东聚合有机硅材料有限公司 | Preparation method of methyl phenyl vinyl silicone resin |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109762167A (en) * | 2018-12-14 | 2019-05-17 | 中国科学院深圳先进技术研究院 | A kind of LED small-size chips heat conductive insulating die bond material and preparation method thereof |
| CN110903808A (en) * | 2019-11-07 | 2020-03-24 | 烟台德邦科技有限公司 | Epoxy-modified high-refractive-index LED packaging silica gel and preparation method thereof |
| CN111004605A (en) * | 2019-12-21 | 2020-04-14 | 东莞市贝特利新材料有限公司 | Self-adhesive organic silicon liquid silicone rubber for bonding glass substrate and forming process thereof |
| CN114752345A (en) * | 2022-03-09 | 2022-07-15 | 苏州艾迪亨斯胶粘技术有限公司 | Bi-component self-adhesive liquid silicone rubber and preparation method thereof |
| CN117467404A (en) * | 2023-12-25 | 2024-01-30 | 拓迪化学(上海)股份有限公司 | Double-component addition type organic silicon adhesive as well as preparation method and application thereof |
| CN117467404B (en) * | 2023-12-25 | 2024-04-19 | 拓迪化学(上海)股份有限公司 | Double-component addition type organic silicon adhesive as well as preparation method and application thereof |
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