CN104788677B - Phenyl-based hydrogen-based silicone resin of T chain links base containing H and preparation method thereof - Google Patents
Phenyl-based hydrogen-based silicone resin of T chain links base containing H and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a kind of phenyl-based hydrogen-based silicone resin of T chain links base containing H and preparation method thereof, the phenyl-based hydrogen-based silicone resin phenyl-based hydrogen-based silicone resin of T chain links base containing H has following general structural formula：(R1 3SiO1/2)a(R2 2SiO2/2)b(R3SiO3/2)c, wherein, (R1 3SiO1/2)aFor simple function group chain link, (R2 2SiO2/2)bFor difunctional chain link, (R3SiO3/2)cFor trifunctional chain link, a=0.2 0.3, b=0.05 0.2, c=0.55 0.65, and a+b+c=1；Wherein, R1For hydrogen-based or the alkyl with 13 carbon atoms, R2For phenyl or the alkyl with 13 carbon atoms, R3For hydrogen-based, phenyl or the alkyl with 13 carbon atoms.The phenyl-based hydrogen-based silicone resin of T chain links base containing H of the present invention, without using solvent, and can effectively improve the crosslink density of solidfied material, improve anti-Sization ability.
Description
Technical field
The present invention relates to the field of chemical synthesis, the phenyl-based hydrogen-based silicone resin and its system of more particularly to a kind of T chain links base containing H
Preparation Method.
Background technology
LED is Light Emitting Diode (light emitting diode) english abbreviation, is that one kind directly can be by electric energy
It is converted into the solid-state semiconductor device of visible ray.LED internal characteristicses determine that it is the most perfect light source for substituting conventional light source.
LED encapsulation material mainly has epoxy resin, polycarbonate, polymethyl methacrylate, glass, organosilicon material etc.
High transparency material.Wherein polycarbonate, polymethyl methacrylate, glass etc. is used as outer layer lens material；Epoxy resin, it is modified
Epoxy resin, organosilicon material etc. can act also as lens material mainly as encapsulating material.And high performance organo-silicon material will be into
One of encapsulation direction for high-end LED encapsulation material.
The principle of solidification of organosilicon encapsulating material is usually to do base polymer with the silicones containing vinyl, containing multiple
The polysiloxane of Si -- H bond makees crosslinking agent, and platinum complex is made into encapsulating compound as catalyst, utilizes the Si- of organosilicon polymer
CH=CH2With Si-H in the presence of catalyst, occur hydrosilylation addition reaction and crosslinking curing.Organosilicon material in LED encapsulation
The key link is exactly the containing hydrogen silicone oil or hydrogeneous silicones for synthesizing high index of refraction in material research and development.High index of refraction containing hydrogen silicone oil is basic
It is to be prepared using open loops such as hydrogeneous ring body, aminomethyl phenyl ring bodies, but the line style crosslinking agent synthesized in this way, carrying out silicon
During hydrogenating addition reaction, reaction speed is slower, and the product strength obtained after solidification is poor.The Silicon Containing Hydrogen tree of high index of refraction
The preparation majority of fat is synthesized using the hydrolytic condensation of alkoxy silane.
What existing method had just together adds organic solvent, alkoxy silane, catalyst etc. in the preparation starting stage
Stirring.In fact, the starting stage is hydrolyzed in alkoxy silane, the dropwise addition speed of water need to be only controlled without adding in solvent, course of reaction
Degree, it is possible to control hydrolysis rate, reaction is gentle.Moreover, being added without organic solvent, reaction efficiency can be improved, reaction is reduced secondary
Product, reduces the solid salt impurity in synthesized silicones.Also in its preparation method having, (R3SiO3/2)bFor trifunctional
Chain link, R3For phenyl or the alkyl with 1~3 carbon atom.This allows for synthesized phenyl-based hydrogen-based silicone resin only in chain
End has hydrogen-based function key.
The content of the invention
Based on this, it is necessary to provide one kind without using solvent, and the crosslink density of solidfied material can be effectively improved, improve
The phenyl-based hydrogen-based silicone resin of T chain links base containing H of anti-Sization ability.
A kind of phenyl-based hydrogen-based silicone resin of T chain links base containing H, phenyl-based hydrogen-based silicone resin has following general structural formula：
(R1 3SiO1/2)a(R2 2SiO2/2)b(R3SiO3/2)c
Wherein, (R1 3SiO1/2)aFor simple function group chain link, (R2 2SiO2/2)bFor difunctional chain link, (R3SiO3/2)cFor three
Functional group's chain link, a=0.2-0.3, b=0.05-0.2, c=0.55-0.65, and molar percentage meets a+b+c=1；
Wherein, R1For hydrogen-based or the alkyl with 1-3 carbon atom, R2For phenyl or the alkyl with 1-3 carbon atom,
R3For hydrogen-based, phenyl or the alkyl with 1-3 carbon atom.
In one of the embodiments, the R1For hydrogen-based or methyl.
In one of the embodiments, the R2For phenyl or methyl.
In one of the embodiments, the R3Containing hydrogen-based, the R3Also include phenyl or methyl.
Another object of the present invention is to provide a kind of preparation method of the phenyl-based hydrogen-based silicone resin of T chain links base containing H.
A kind of preparation method of the phenyl-based hydrogen-based silicone resin of T chain links base containing H, comprises the following steps：
(1) alkoxy silane, end-capping reagent are mixed, 8-12min is mixed at a temperature of 50~60 DEG C；
(2) stirred at a temperature of 50~60 DEG C and water be added dropwise and the mixture of acid catalyst, after dripping, at 60 DEG C after
Continuous reaction 2~4 hours；
(3) mixture obtained by step (2) is distilled at 90~100 DEG C, gained residue is added to alkalescence after cooling
Nertralizer is neutralized, and is filtered；
(4) by filtrate obtained by step (3), vacuum distillation removes low molecule at 100~150 DEG C, so as to obtain described benzene
Base based hydrogen-based silicone resin.
In one of the embodiments, in step (1), described alkoxy silane has trimethoxy hydrogen silane, described
Alkoxy silane also at least include selected from phenyltrimethoxysila,e, phenyl triethoxysilane, dimethoxydiphenylsilane,
In diphenyl diethoxy silane, aminomethyl phenyl dimethoxysilane, MTMS, MTES
It is one or more of.
In one of the embodiments, the end-capping reagent described in step (1) is HMDO, tetramethyl disiloxane
In one or more.
In one of the embodiments, the acid catalyst described in step (2) is selected from hydrochloric acid, sulfuric acid, acetic acid, fluoroform sulphur
One or more in acid；And the consumption of the acidic catalyst be the alkoxy silane and the end-capping reagent mole it
The 0.5% of sum.
In one of the embodiments, wherein, water described in step (2) is deionized water, and the consumption of deionized water is
The 50%-100% of water gross mass needed for two degrees of functionality, the hydrolysis of three-functionality-degree alkoxy silane.
In one of the embodiments, the antalkali described in step (3) is selected from sodium acid carbonate, tetramethyl hydrogen-oxygen
Change the one or more in ammonium.
The phenyl-based hydrogen-based silicone resin of T chain links base containing H of the present invention, it is hydrogeneous as T chain links using trimethoxy silane
The source of base so that synthesized phenyl-based hydrogen-based silicone resin also has hydrogen based group on the skeleton of polymer, can effectively carry
The crosslink density of high solidification thing, improves anti-Sization ability.
The phenyl-based hydrogen-based silicone resin of T chain links base containing H of the present invention, this method is and prepared without using solvent
Phenyl-based hydrogen-based silicone resin be to have the polymer of hydrogen-based function key on hydrogen-based end-blocking and skeleton, be connected to the hydrogen on polymer backbone
Base group can effectively improve the crosslink density of solidfied material, improve anti-Sization ability.
It is added without in the preparation method of the phenyl-based hydrogen-based silicone resin of T chain links base containing H of the present invention, course of reaction organic
Solvent, improves reaction efficiency, reduces byproduct of reaction, reduces the solid salt impurity in synthesized silicones.
Embodiment
Present embodiments provide a kind of phenyl-based hydrogen-based silicone resin of T chain links base containing H.
A kind of phenyl-based hydrogen-based silicone resin of T chain links base containing H, phenyl-based hydrogen-based silicone resin has following general structural formula：
(R1 3SiO1/2)a(R2 2SiO2/2)b(R3SiO3/2)c
Wherein, (R1 3SiO1/2)aFor simple function group chain link, (R2 2SiO2/2)bFor difunctional chain link, (R3SiO3/2)cFor three
Functional group's chain link, the molar percentage of wherein each functional group's chain link is：A=0.2-0.3, b=0.05-0.2, c=0.55-
0.65, and a+b+c=1；
Wherein, R1For hydrogen-based or the alkyl with 1-3 carbon atom, R2For phenyl or the alkyl with 1-3 carbon atom,
R3For hydrogen-based, phenyl or the alkyl with 1-3 carbon atom.
Preferably, the R1For hydrogen-based or methyl；The R2For phenyl or methyl, the R3Containing hydrogen-based, the R3Also wrap
Include phenyl or methyl.
The present embodiment additionally provides a kind of preparation method of the phenyl-based hydrogen-based silicone resin of T chain links base containing H.
A kind of preparation method of the phenyl-based hydrogen-based silicone resin of T chain links base containing H, comprises the following steps：
(1) alkoxy silane, end-capping reagent are mixed into (((the R that alkoxy silane belongs in formula2 2SiO2/2)b
(R3SiO3/2)c, (the R that end-capping reagent belongs in formula1 3SiO1/2)a), mix 8-12min at a temperature of 50~60 DEG C；It is described
Alkoxy silane there is trimethoxy hydrogen silane, the alkoxy silane also at least include selected from phenyltrimethoxysila,e,
Phenyl triethoxysilane, dimethoxydiphenylsilane, diphenyl diethoxy silane, aminomethyl phenyl dimethoxysilane,
One or more in MTMS, MTES.Described end-capping reagent be HMDO,
One or more in tetramethyl disiloxane.
(2) stirred at a temperature of 50~60 DEG C and water is added dropwise and the mixture of acid catalyst, ionized water and acid catalyst are mixed
After closing uniformly, it is added dropwise dropwise, after dripping, continues to react 2~4 hours at 60 DEG C；Described acid catalyst is selected from salt
One or more in acid, sulfuric acid, acetic acid, trifluoromethanesulfonic acid；And the consumption of the acidic catalyst is the alkoxy silane
With the 0.5% of the mole sum of the end-capping reagent.Described water is deionized water, and the consumption of deionized water is two functions
The 50%-100% of water gross mass needed for degree, the hydrolysis of three-functionality-degree alkoxy silane.
(3) mixture obtained by step (2) is distilled at 90~100 DEG C, gained residue is added to alkalescence after cooling
Nertralizer is neutralized, and is filtered；Described antalkali is one kind or several in sodium acid carbonate, TMAH
Kind.
(4) by filtrate obtained by step (3), vacuum distillation removes low molecule at 100~150 DEG C, so as to obtain described benzene
Base based hydrogen-based silicone resin.
Embodiment 1
By 24g dimethoxydiphenylsilanes, 50g phenyltrimethoxysila,es, 1.2g trimethoxies hydrogen silane and 16g tetra-
Tetramethyldisiloxane is added in 250mL four-hole boiling flasks, in 55 DEG C, constant agitation 10 minutes.Afterwards at 60 DEG C, it is added dropwise
The mixed liquor of 10g deionized waters and 50% sulfuric acid, is carried out about 40 minutes.Back flow reaction 4h.Use distilling apparatus instead, be warming up to
100 DEG C, accessory substance is gone out with water pump vacuum distillation, to system bubble-free.Gained residue is cooled to after 50 DEG C, adds 8g
NaHCO3, 30 minutes solution of stir about is changed into neutral, filtered with filter paper.Afterwards, at 150 DEG C, vacuum oil pump vacuum distillation is used
Go out lower-molecular substance, so as to obtain the phenyl-based hydrogen-based silicone resin of T chain links base containing H of 55g water white transparencies.
The phenyl-based hydrogen-based silicone resin viscosity 1300mPa.s (25 DEG C) of T chain links base containing H of gained, index of refraction in the present embodiment
1.533, hydrogen content 0.43%.
Embodiment 2
By 272g diphenyl diethoxy silanes, 624g phenyl triethoxysilanes, 12g trimethoxies hydrogen silane, 16g six
Tetramethyldisiloxane and 148g tetramethyl disiloxanes are added in 2L four-hole boiling flasks, in 60 DEG C, constant agitation 8 minutes.Afterwards 60
DEG C when, be added dropwise 118g deionized waters and hydrochloric acid mixed solution, be added dropwise about 40 minutes.Back flow reaction 4h.Use distilling apparatus instead,
90 DEG C are warming up to, accessory substance is gone out with water pump vacuum distillation, to system bubble-free.Gained residue is cooled to after 50 DEG C, adds 80g
NaHCO3, 30 minutes solution of stir about is changed into neutral, filtered with filter paper.Afterwards, at 130 DEG C, vacuum oil pump vacuum distillation is used
Go out lower-molecular substance, so as to obtain the phenyl-based hydrogen-based silicone resin of T chain links base containing H of 520g water white transparencies.
The phenyl-based hydrogen-based silicone resin viscosity 2400mPa.s (25 DEG C) of T chain links base containing H of gained, index of refraction in the present embodiment
1.541, hydrogen content 0.38%.
Embodiment 3
By 12g dimethoxydiphenylsilanes, 12g aminomethyl phenyls dimethoxysilane, 52g phenyltrimethoxysila,es,
10g MTMSs, 1.2g trimethoxies hydrogen silane and 16g tetramethyl disiloxanes are added in 250mL four-hole boiling flasks,
In 50 DEG C, constant agitation 12 minutes.Afterwards 60 DEG C when, be added dropwise the mixed liquor of 10g deionized waters and 50% sulfuric acid, carry out big
About 40 minutes.Back flow reaction 2h.Use distilling apparatus instead, be warming up to 100 DEG C, accessory substance is gone out with water pump vacuum distillation, to system without
Bubble.Gained residue is cooled to after 50 DEG C, adds 8g NaHCO3, 30 minutes solution of stir about is changed into neutral, uses filter paper mistake
Filter.Afterwards, at 100 DEG C, lower-molecular substance is gone out with vacuum oil pump vacuum distillation, so that the T chain links for obtaining 55g water white transparencies contain
The phenyl-based hydrogen-based silicone resin of H bases.
The phenyl-based hydrogen-based silicone resin viscosity 1200mPa.s (25 DEG C) of T chain links base containing H of gained, index of refraction in the present embodiment
1.509, hydrogen content 0.40%.
Embodiment 4
By 9.4g dimethoxydiphenylsilanes, 77g phenyltrimethoxysila,es, 4.1g trimethoxies hydrogen silane and 40g
Tetramethyl disiloxane is added in 500mL four-hole boiling flasks, in 55 DEG C, constant agitation 10 minutes.Afterwards at 60 DEG C, it is added dropwise
The mixed liquor of 37g deionized waters and 50% sulfuric acid, is carried out about 40 minutes.Back flow reaction 4h.Use distilling apparatus instead, be warming up to
100 DEG C, accessory substance is gone out with water pump vacuum distillation, to system bubble-free.Gained residue is cooled to after 50 DEG C, adds 25g
NaHCO3, 30 minutes solution of stir about is changed into neutral, filtered with filter paper.Afterwards, at 150 DEG C, vacuum oil pump vacuum distillation is used
Go out lower-molecular substance, so as to obtain the phenyl-based hydrogen-based silicone resin of T chain links base containing H of 80g water white transparencies.
The phenyl-based hydrogen-based silicone resin viscosity 2105mPa.s (25 DEG C) of T chain links base containing H of gained, index of refraction in the present embodiment
1.515, hydrogen content 0.26%.
The phenyl-based hydrogen-based silicone resin of T chain links base containing H of the present invention, it is hydrogeneous as T chain links using trimethoxy silane
The source of base so that synthesized phenyl-based hydrogen-based silicone resin also has hydrogen based group on the skeleton of polymer, can effectively carry
The crosslink density of high solidification thing, improves anti-Sization ability.
The phenyl-based hydrogen-based silicone resin of T chain links base containing H of the present invention, this method is and prepared without using solvent
Phenyl-based hydrogen-based silicone resin be to have the polymer of hydrogen-based function key on hydrogen-based end-blocking and skeleton, be connected to the hydrogen on polymer backbone
Base group can effectively improve the crosslink density of solidfied material, improve anti-Sization ability.
It is added without in the preparation method of the phenyl-based hydrogen-based silicone resin of T chain links base containing H of the present invention, course of reaction organic
Solvent, improves reaction efficiency, reduces byproduct of reaction, reduces the solid salt impurity in synthesized silicones.
Embodiment described above only expresses the several embodiments of the present invention, and it describes more specific and detailed, but simultaneously
Therefore the limitation to the scope of the claims of the present invention can not be interpreted as.It should be pointed out that for one of ordinary skill in the art
For, without departing from the inventive concept of the premise, various modifications and improvements can be made, these belong to the guarantor of the present invention
Protect scope.Therefore, the protection domain of patent of the present invention should be determined by the appended claims.
Claims (10)
1. a kind of phenyl-based hydrogen-based silicone resin of T chain links base containing H, it is characterised in that
Phenyl-based hydrogen-based silicone resin has following general structural formula：
(R1 3SiO1/2)a(R2 2SiO2/2)b(R3SiO3/2)c
Wherein, (R1 3SiO1/2)aFor simple function group chain link, (R2 2SiO2/2)bFor difunctional chain link, (R3SiO3/2)cFor trifunctional
Group's chain link, a=0.2-0.3, b=0.05-0.2, c=0.55-0.65, and a+b+c=1；
Wherein, R1For hydrogen-based or the alkyl with 1-3 carbon atom, R2For phenyl or the alkyl with 1-3 carbon atom, R3For
Hydrogen-based, phenyl or the alkyl with 1-3 carbon atom；
The phenyl-based hydrogen-based silicone resin, which is prepared by the following method, to be obtained：
(1) alkoxy silane, end-capping reagent are mixed, 8-12min is mixed at a temperature of 50~60 DEG C；
(2) stirred at a temperature of 50~60 DEG C and water is added dropwise and the mixture of acid catalyst, after dripping, continue anti-at 60 DEG C
Answer 2~4 hours；
(3) mixture obtained by step (2) is distilled at 90~100 DEG C, gained residue is added to alkalescence neutralization after cooling
Agent is neutralized, and is filtered；
(4) by filtrate obtained by step (3), vacuum distillation removes low molecule at 100~150 DEG C, so as to obtain described phenyl hydrogen
Base silicones.
2. the phenyl-based hydrogen-based silicone resin of T chain links base containing H according to claim 1, it is characterised in that the R1For hydrogen-based or
Methyl.
3. the phenyl-based hydrogen-based silicone resin of T chain links base containing H according to claim 1, it is characterised in that the R2For phenyl or
Methyl.
4. the phenyl-based hydrogen-based silicone resin of T chain links base containing H according to claim 1, it is characterised in that the R3Containing hydrogen-based,
The R3Also include phenyl or methyl.
5. a kind of preparation method of the phenyl-based hydrogen-based silicone resin of any one of claim 1-4 T chain links base containing H, it is characterised in that
Comprise the following steps：
(1) alkoxy silane, end-capping reagent are mixed, 8-12min is mixed at a temperature of 50~60 DEG C；
(2) stirred at a temperature of 50~60 DEG C and water is added dropwise and the mixture of acid catalyst, after dripping, continue anti-at 60 DEG C
Answer 2~4 hours；
(3) mixture obtained by step (2) is distilled at 90~100 DEG C, gained residue is added to alkalescence neutralization after cooling
Agent is neutralized, and is filtered；
(4) by filtrate obtained by step (3), vacuum distillation removes low molecule at 100~150 DEG C, so as to obtain described phenyl hydrogen
Base silicones.
6. the preparation method of the phenyl-based hydrogen-based silicone resin of T chain links base containing H according to claim 5, it is characterised in that：Step
(1) in, described alkoxy silane has trimethoxy hydrogen silane, and the alkoxy silane also at least includes being selected from phenyl front three
TMOS, phenyl triethoxysilane, dimethoxydiphenylsilane, diphenyl diethoxy silane, aminomethyl phenyl diformazan
One or more in TMOS, MTMS, MTES.
7. the preparation method of the phenyl-based hydrogen-based silicone resin of T chain links base containing H according to claim 5, it is characterised in that step
(1) end-capping reagent described in is the one or more in HMDO, tetramethyl disiloxane.
8. the preparation method of the phenyl-based hydrogen-based silicone resin of T chain links base containing H according to claim 5, it is characterised in that step
(2) acid catalyst described in is the one or more in hydrochloric acid, sulfuric acid, acetic acid, trifluoromethanesulfonic acid；And the acidic catalyst
The consumption of agent is the 0.5% of the mole sum of the alkoxy silane and the end-capping reagent.
9. the preparation method of the phenyl-based hydrogen-based silicone resin of T chain links base containing H according to claim 5, it is characterised in that its
In, the water described in step (2) is deionized water, and the consumption of deionized water is two degrees of functionality, three-functionality-degree alkoxy silane water
The 50%-100% of water gross mass needed for solution.
10. the preparation method of the phenyl-based hydrogen-based silicone resin of T chain links base containing H according to claim 5, it is characterised in that step
Suddenly the antalkali described in (3) is the one or more in sodium acid carbonate, TMAH.
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| CN105906810B (en) * | 2016-04-26 | 2019-08-06 | 广东标美硅氟新材料有限公司 | A kind of preparation method of organopolysiloxane resins |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101891893A (en) * | 2010-07-23 | 2010-11-24 | 深圳市安品有机硅材料有限公司 | Preparation method of phenyl-based hydrogen-based silicone resin for encapsulating LED |
| CN103781852A (en) * | 2011-07-07 | 2014-05-07 | 道康宁东丽株式会社 | Curable silicon composition, cured product thereof, and optical semiconductor device |
| CN104356654A (en) * | 2014-10-31 | 2015-02-18 | 汕头市骏码凯撒有限公司 | High refractive index silicon resin curing substance and LED luminous diode sealed by curing substance |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101891893A (en) * | 2010-07-23 | 2010-11-24 | 深圳市安品有机硅材料有限公司 | Preparation method of phenyl-based hydrogen-based silicone resin for encapsulating LED |
| CN103781852A (en) * | 2011-07-07 | 2014-05-07 | 道康宁东丽株式会社 | Curable silicon composition, cured product thereof, and optical semiconductor device |
| CN104356654A (en) * | 2014-10-31 | 2015-02-18 | 汕头市骏码凯撒有限公司 | High refractive index silicon resin curing substance and LED luminous diode sealed by curing substance |
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