CN104140679B - The silicon composition of a kind of main chain containing hydrocarbylene structure and preparation method thereof - Google Patents
The silicon composition of a kind of main chain containing hydrocarbylene structure and preparation method thereof Download PDFInfo
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Abstract
The present invention provides a kind of silicon composition of the main chain containing hydrocarbylene structure, is made up of tetra- parts of A, B, C and D, and (A) is the compound shown in formula (1)：(1), (B) is the compound shown in formula (2)：
Description
Technical field
The present invention relates to field of organic silicon, more particularly, to a kind of silicon composition of main chain containing hydrocarbylene structure
And preparation method thereof.
Background technology
LED is referred to as forth generation lighting source or green light source as a kind of new green light source product.With LED
Illuminating industry flourishes, and high-power, high brightness, the LED component of long life requirement continue to bring out, it is necessary to a kind of high-performance
Encapsulating material come meet LED encapsulation requirement.This material mainly plays a part of to seal and protect chip normal work.
Organosilicon material is due to being that various LED application is carried with excellent resistant of high or low temperature and anti-ultraviolet radiation ability
For extensive Embedding Material, lens material, binding agent, fluid sealant and protective coating product.But with the high speed of LED industry
Development, to diversified developments such as brightness, purposes, packaging process, designs the need for generate to different hardness, bigger refractive index seal
The demand of package material, while in order to ensure the reliability after packaging, selecting suitable hardness, the material of caking property is also very heavy
Want.The research emphasis of current LED organosilicon material for packaging is mainly refractive index, thermal conductivity, the mechanical strength for improving material
And in terms of reduction coefficient of thermal expansion, this also will be very stern challenge to organosilicon encapsulating material research and development.
The content of the invention
It is an object of the invention to provide a kind of curable organosilicon composition of component of main chain containing hydrocarbylene structure, it is consolidated
Changing product has excellent heat resistance, transparent and higher hardness, and with good cold-resistant thermal impact, thus be to make
The ideal material encapsulated for optical element.
Present invention firstly provides a kind of silicon composition of main chain containing hydrocarbylene structure, by tetra- part groups of A, B, C and D
Into,
(A) it is the compound shown in formula (1)：
(1)
Wherein, each R stands alone as monovalent hydrocarbon or alkoxy with 1 ~ 6 carbon atom, a, b, c be in 1 ~ 20 just
Integer；X represents divalent group, can be one or both of siloxane unit, penylene unit or alkylidene unit；
(B) it is the compound shown in formula (2)：
（2）
Wherein, respectivelyStand alone as monovalent hydrocarbon or alkoxy with 1 ~ 6 carbon atom, and 1 at least withinFor benzene
Base, d, e are the positive integer in 1 ~ 20；
（C）For hydrosilylation catalyst,（D）For 1- ethynylcyclohexanols or methylacetylenyl alcohol.
A kind of preparation method of the solidfied material of silicon composition of the above-mentioned main chain containing hydrocarbylene structure is provided in addition, wrapped
Include following steps：
S1. the synthesis of component A：
S11. it is 1,4- is double（Dimethylethyloxy silicyl）Benzene, dimethoxydiphenylsilane, dimethylformamide dimethyl oxygen
Base silane, 2,5- are double（Dimethylethyloxy silicyl）Two rings [2.2.1]-heptane, vinyl methyl dimethoxysilane, second
Alkenyl dimethyl methoxy silane and hexamethylene mixing, are warming up to 60 ~ 80 DEG C,
Or by dimethoxydiphenylsilane, dimethyldimethoxysil,ne）, 2,5- it is double（Dimethylethyloxy first silicon
Alkyl）Two rings [2.2.1]-heptane, vinyl methyl dimethoxysilane, vinyl-dimethyl methoxylsilane and hexamethylene are mixed
Close, be warming up to 60 ~ 80 DEG C；
S12. it is slowly added dropwise into NaOH solution, the described time being slowly added dropwise is 50 ~ 60 minutes；
S13. temperature rising reflux reaction is carried out, decontamination is produced；
S2. the synthesis of B component：
S21. it is 2,5- is double（Dimethylethyloxy silicyl）Two rings [2.2.1]-heptane, diphenyl dimethoxy silicon
Alkane, dimethyldimethoxysil,ne, two hydrogen-based tetramethyl disiloxanes and hexamethylene mixing, are warming up to 40 ~ 60 DEG C；
S22. it is slowly added dropwise into trifluoromethane sulfonic acid solution, the described time being slowly added dropwise is 50 ~ 60 minutes；
S23. temperature rising reflux reaction is carried out, decontamination is produced；
S3. component A obtained by S1 and the B component obtained by S2 are mixed, wherein carbon-to-carbon double bond total in component A and B component
In total Si -- H bond mole the ratio between be 0.95 ~ 1:1,
Compound containing platinum is added, described platinum element quality accounts for the 50ppm of A and B gross weight,
1- alkynyl cyclohexanol is added, wherein, described 1- alkynyl cyclohexanol accounts for the 0.03% of A and B gross weight,
Controlling reaction temperature is produced at 130 ~ 170 DEG C after 30 to 90 minutes.
By weight, described Isosorbide-5-Nitrae-bis-（Dimethylethyloxy silicyl）Benzene, dimethoxydiphenylsilane, two
Methyl dimethoxysilane, 2,5- are double（Dimethylethyloxy silicyl）Two rings [2.2.1]-heptane, vinyl methyl diformazan
The ratio of TMOS, vinyl-dimethyl methoxylsilane and hexamethylene is 11 ~ 13：14~16：4~6：3~5：0.4~0.6：
1.9~2.1：100.
By weight, described dimethoxydiphenylsilane, dimethyldimethoxysil,ne）, 2,5- it is double（Dimethyl
Triethoxysilyl）Two rings [2.2.1]-heptane, vinyl methyl dimethoxysilane, vinyl-dimethyl methoxylsilane
Ratio with hexamethylene is 18 ~ 22：5~7：4~6：0.5~0.7：2.5~3.0：100.
By weight, 2 described, 5- is double（Dimethylethyloxy silicyl）Two rings [2.2.1]-heptane, diphenyl
Dimethoxysilane, dimethyldimethoxysil,ne, the ratio of two hydrogen-based tetramethyl disiloxanes and hexamethylene are 3 ~ 5：23~
27：5~10：1.5~2.5：100.
According to the present invention based on curable organosilicon composition of the main chain containing hydrocarbylene structure, the solidfied material has excellent
Heat resistance, transparent and higher hardness, and with good cold-resistant thermal impact, it can be used as the encapsulation of optical element
Material.
Embodiment
The present invention is further described with reference to specific embodiment.Unless stated otherwise, the present invention use reagent,
Apparatus and method are the art routinely reagent, equipment and conventional use of method purchased in market.
<Component A>
Component A is that each molecule contains carbon-to-carbon double bond of at least three directly with silicon atom bonding, and main chain contains alkylene
The compound of structure, it is by below formula (1) Suo Shi：
（1）
Wherein, R represents the unsubstituted or substituted monovalent hydrocarbon or alkoxy with 1 ~ 6 carbon atom independently of one another,
And 3 R of wherein at least are that vinyl and at least one R directly with silicon atom bonding is phenyl.R can selected from methyl, ethyl,
The saturations such as propyl group, butyl, cyclohexyl（Ring）Alkyl；The alcoxyls such as methoxyl group, ethyoxyl, propoxyl group, isopropoxy, butoxy
Base；End carries Cl, NH2、SH、N3, ester group, epoxy radicals, the alkyl of the functional group such as NCO；Phenyl and the end of the chain it is carbon containing-
The aliphatic olefin alkyl of carbon double bond, be specially：Vinyl, pi-allyl etc..
A, b, c are the positive integer in 1 ~ 20.X represents divalent group, can be below formula（3）Shown siloxanes
Unit：
(3)
Wherein,The unsubstituted or substituted monovalent hydrocarbon with 1 ~ 6 carbon atom is represented independently of one another, can be selected from
The saturations such as methyl, ethyl, propyl group, butyl, cyclohexyl（Ring）Alkyl；Methoxyl group, ethyoxyl, propoxyl group, isopropoxy, fourth oxygen
The alkoxies such as base；End carries Cl, NH2、SH、N3, ester group, epoxy radicals, the alkyl of the functional group such as NCO；Phenyl and
The aliphatic olefin alkyl of end of the chain carbon-carbon double key, be specially：Vinyl, pi-allyl etc..N is the positive integer in 1 ~ 10；
It can also be below formula（4）Shown penylene unit：
(4)
It can also be below formula（5）Shown alkylidene unit：
(5)
Wherein, m is the positive integer of 1 ~ 6 scope.
X can be the one or more in above-mentioned three kinds of construction units.
Two substituents on norbornane group can be at 2,5, be below formula（6）Shown structure：
（6）
Can also be in 2,6, be below formula（7）Shown structure：
（7）
On the premise of composition overall performance is not influenceed, the relative position of two substituents on norbornane group can
To be the mixture of one of which or both isomers.
<B component>
The B component of the present invention contains sub- norbornane based structures and with side base benzene for the main chain with 2 Si-H base end sockets
The linear siloxanes of base, are below formula（2）It is shown：
（2）
Wherein,Represent independently of one another the unsubstituted or substituted monovalent hydrocarbon or alkoxy with 1 ~ 6 carbon atom and
1 at least withinFor phenyl,Can be selected from saturations such as methyl, ethyl, propyl group, butyl, cyclohexyl（Ring）Alkyl；Methoxy
The alkoxies such as base, ethyoxyl, propoxyl group, isopropoxy, butoxy；End carries Cl, NH2、SH、N3, ester group, epoxy radicals, isocyanide
The alkyl of the functional groups such as perester radical；Phenyl.D, e are the positive integer in 1 ~ 20.Containing sub- norbornane based structures in the component
Unit with（A）It is identical containing sub- norbornane based structures unit in component.
<Component C>
The component C of the present invention is hydrosilylation catalyst, including platinum class, palladium class, rhodium class etc. are transition metal-catalyzed
Agent.In view of the cost and raw material sources of catalyst, particularly preferably H2PtCl6·6H2O, or H2PtCl6·6H2O is with containing second
The complex compound of the polysiloxane of alkenyl.
The allotment amount of component C is as effective dose during catalyst for addition reaction of hydrogen and silicon, with platinum group
Mass conversion, equivalent to component A and 0.1 ~ 1000ppm scopes of B component total amount, more preferably 0.5 ~ 100ppm scopes.
<D components>
The present invention D components be added on the premise of cured of composition outward appearance and overall performance is not influenceed other
Additive, for example, working time during in order to extend shelf life and use, adds reaction suppressor 1- ethynylcyclohexanols or first
Ethyl-acetylene base alcohol.A certain amount of antioxidant and tackifier can also be added.
It is the description to specific implementation details of the present invention as follows, but the present invention is not limited to these implementations as shown below
Example.
The preparation of the A1 components of embodiment 1
（1）1,4- is added in the four-hole boiling flask that 5L is provided with agitator, condenser pipe, thermometer and constant pressure funnel double（Two
Methyl ethoxy silicyl）Benzene 120g（0.43mol）, dimethoxydiphenylsilane 150g（0.61mol）, dimethylformamide dimethyl
TMOS 50g（0.42mol）, 2,5- it is double（Dimethylethyloxy silicyl）Two rings [2.2.1]-heptane 40g
（0.13mol）, vinyl methyl dimethoxysilane 5g（0.038mol）, vinyl-dimethyl methoxylsilane 20g
（0.17mol）And hexamethylene 1000g, stir and be warming up to 70 DEG C；
（2）At 70 DEG C, the mixed liquor 700g of NaOH and water is added dropwise, time for adding is controlled within an hour；
（3）Temperature rising reflux is dripped to react 5 hours；
（4）Branch vibration layer, neutrality is washed to by polymer and solvent content；
（5）Remove and target product A1 components are produced after unreacted raw material and solvent.
The preparation of the A2 components of embodiment 2
（1）Diphenyl diformazan is added in the four-hole boiling flask that 5L is provided with agitator, condenser pipe, thermometer and constant pressure funnel
TMOS 200g（0.82mol）, dimethyldimethoxysil,ne 60g（0.5mol）, 2,5- it is double（Dimethylethyloxy monosilane
Base）Two rings [2.2.1]-heptane 50g（0.17mol）, vinyl methyl dimethoxysilane 6g（0.045mol）, vinyl-dimethyl
Methoxylsilane 27g（0.23mol）And hexamethylene 1000g, stir and be warming up to 70 DEG C；
（2）At 70 DEG C, the mixed liquor 600g of NaOH and water is added dropwise, time for adding is controlled within an hour；
（3）Temperature rising reflux is dripped to react 5 hours；
（4）Branch vibration layer, neutrality is washed to by polymer and solvent content；
（5）Remove and target product A2 components are produced after unreacted raw material and solvent.
The preparation of the B component of embodiment 3
（1）2,5- is added in the four-hole boiling flask that 5L is provided with agitator, condenser pipe, thermometer and constant pressure funnel double（Two
Methyl ethoxy silicyl）Two rings [2.2.1]-heptane 40g（0.19mol）, dimethoxydiphenylsilane 250g
（1.15mol）, dimethyldimethoxysil,ne 80g（0.67mol）, two hydrogen-based tetramethyl disiloxane 20g（0.15mol）And ring
Hexane 1000g, stirs and is warming up to 50 DEG C；
（2）At 50 DEG C, the mixed liquor 700g of trifluoromethane sulfonic acid and water is added dropwise, time for adding is controlled within an hour；
（3）Temperature rising reflux is dripped to react 4 hours；
（4）Branch vibration layer, neutrality is washed to by polymer and solvent content；
（5）Remove and target product B component is produced after unreacted raw material and solvent.
Embodiment 4
（A）100 mass parts are by the A1 products obtained by synthetic example 1.
（B）The ratio between amount of material of Si -- H bond total in total carbon-to-carbon double bond/B component=0.92 in A1 components
（C）Relative to A1, the gross mass of B component, platinum element quality is converted to for 50ppm.
（D）The 1- alkynyl cyclohexanol of 0.03 mass parts.
After said mixture is stirred, it is put into 150 DEG C of baking boxs and obtains cured product after baking 1h.
Embodiment 5
（A）100 mass parts are by the A2 products obtained by synthetic example 1.
（B）The ratio between amount of material of Si -- H bond total in total carbon-to-carbon double bond/B component=0.88 in A2 components
（C）Relative to A2, the gross mass of B component, platinum element quality is converted to for 50ppm.
（D）The 1- alkynyl cyclohexanol of 0.03 mass parts.
After said mixture is stirred, it is put into 150 DEG C of baking boxs and obtains cured product after baking 1h.
Using existing conventional technical means, the performance to the cured product obtained by above-described embodiment 4, embodiment 5 is entered
Row system evaluation, its result is as shown in table 1 below.
Cured product performance table obtained by the embodiment 4 and 5 of table 1.
As seen from Table 1, properties of product of the invention meet the requirements.
Claims (5)
1. silicon composition of a kind of main chain containing hydrocarbylene structure, it is characterised in that be made up of tetra- parts of A, B, C and D,
Component A is that each molecule contains carbon-to-carbon double bond of at least three directly with silicon atom bonding, and main chain contains hydrocarbylene structure
Compound, A be formula (1) shown in compound：
Wherein, each R stands alone as monovalent hydrocarbon or alkoxy with 1~6 carbon atom, and a, b, c are just whole in 1~20
Number；X represents divalent group, can be one or both of siloxane unit, penylene unit or alkylidene unit,
B is the compound shown in formula (2)：
Wherein, each R ' stands alone as monovalent hydrocarbon or alkoxy with 1~6 carbon atom, and 1 R ' is phenyl at least within,
D, e are the positive integer in 1~20；
C is hydrosilylation catalyst, and D is 1- ethynylcyclohexanols or methylacetylenyl alcohol.
2. a kind of preparation method of the solidfied material of silicon composition of main chain containing hydrocarbylene structure, it is characterised in that including with
Lower step：
The synthesis of S1.A components：
S11. by 1,4- double (dimethylethyloxy silicyl) benzene, dimethoxydiphenylsilane, dimethylformamide dimethyl epoxide silicon
Alkane, 2,5- double (dimethylethyloxy silicyl) two rings [2.2.1]-heptane, vinyl methyl dimethoxysilane, vinyl
Dimethyl methoxy silane and hexamethylene mixing, are warming up to 60~80 DEG C, or by dimethoxydiphenylsilane, dimethyl two
Methoxy silane), 2,5- double (dimethylethyloxy silicyl) two rings [2.2.1]-heptane, vinyl methyl dimethoxy silicon
Alkane, vinyl-dimethyl methoxylsilane and hexamethylene mixing, are warming up to 60~80 DEG C；
S12. it is slowly added dropwise into NaOH solution, the described time being slowly added dropwise is 50~60 minutes；
S13. temperature rising reflux reaction is carried out, decontamination is produced；
The synthesis of S2.B components：
S21. by 2,5- double (dimethylethyloxy silicyl) two rings [2.2.1]-heptane, dimethoxydiphenylsilane, two
Methyl dimethoxysilane, two hydrogen-based tetramethyl disiloxanes and hexamethylene mixing, are warming up to 40~60 DEG C；
S22. it is slowly added dropwise into trifluoromethane sulfonic acid solution, the described time being slowly added dropwise is 50~60 minutes；
S23. temperature rising reflux reaction is carried out, decontamination is produced；
S3. component A obtained by S1 and the B component obtained by S2 are mixed, it is total wherein in carbon-to-carbon double bond total in component A and B component
Si -- H bond mole the ratio between be 0.95~1:1,
Compound containing platinum is added, described platinum element quality accounts for the 50ppm of A and B gross weight,
1- alkynyl cyclohexanol is added, wherein, described 1- alkynyl cyclohexanol accounts for the 0.03% of A and B gross weight, control reaction temperature
Degree is produced at 130~170 DEG C after 30 to 90 minutes.
3. preparation method according to claim 2, it is characterised in that by weight, described Isosorbide-5-Nitrae-bis- (dimethyl second
Epoxide silicyl) benzene, dimethoxydiphenylsilane, dimethyldimethoxysil,ne, double (the dimethylethyloxy first silicon of 2,5-
Alkyl) two rings [2.2.1]-heptane, vinyl methyl dimethoxysilane, vinyl-dimethyl methoxylsilane and hexamethylene
Ratio is 11~13：14~16：4~6：3~5：0.4~0.6：1.9~2.1：100.
4. preparation method according to claim 2, it is characterised in that by weight, described diphenyl dimethoxy
Silane, dimethyldimethoxysil,ne, 2,5- double (dimethylethyloxy silicyl) two rings [2.2.1]-heptane, vinyl first
The ratio of base dimethoxysilane, vinyl-dimethyl methoxylsilane and hexamethylene is 18~22：5~7：4~6：0.5~
0.7：2.5~3.0：100.
5. preparation method according to claim 2, it is characterised in that by weight, double (the dimethyl second of 2 described, 5-
Epoxide silicyl) two rings [2.2.1]-heptane, dimethoxydiphenylsilane, dimethyldimethoxysil,ne, two hydrogen-baseds four
The ratio of tetramethyldisiloxane and hexamethylene is 3~5：23~27：5~10：1.5~2.5：100.
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| TW201005038A (en) * | 2008-04-16 | 2010-02-01 | Shinetsu Chemical Co | Curable polysiloxane composition for optical lens |
| CN102433004A (en) * | 2010-08-26 | 2012-05-02 | 信越化学工业株式会社 | Curable silicone-based composition comprising polycyclic hydrocarbon skeleton containing component |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| TW201005038A (en) * | 2008-04-16 | 2010-02-01 | Shinetsu Chemical Co | Curable polysiloxane composition for optical lens |
| CN102433004A (en) * | 2010-08-26 | 2012-05-02 | 信越化学工业株式会社 | Curable silicone-based composition comprising polycyclic hydrocarbon skeleton containing component |
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