CN108892776A - A kind of organic-silicon-modified epoxy resin and preparation method thereof - Google Patents
A kind of organic-silicon-modified epoxy resin and preparation method thereof Download PDFInfo
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- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
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Abstract
The present invention relates to a kind of organic-silicon-modified epoxy resin and preparation method thereof, the polymethylphenylsiloxane modified bisphenol A type epoxy resin blocked by Q type POSS prepares the silicone-epoxy resin hydridization co-crosslinking structure containing POSS shell.The organic-silicon-modified epoxy resin of gained of the invention has the synergistic effect of the structure of heat-resisting POSS nanometer core and polymethylphenylsiloxane, the heat resistance of epoxy resin can integrally be improved, furthermore, the good flexibility of polysiloxanes can greatly improve the toughness of modified epoxy, can be widely applied for the leading-edge fields such as high-end LED encapsulation, aerospace composite material.
Description
Technical field
The present invention relates to a kind of organic-silicon-modified epoxy resin and preparation method thereof, belong to macromolecule fine chemical technology
Field.
Background technique
Epoxy resin is high with adhesive strength, cure shrinkage is low, hardness is big, wearability is good, processing performance is good, electrical isolation
The advantages that good, raw material of property is easy to get, is low in cost, is widely used in wrapping as materials such as adhesive, packaging plastic, composite resins
Daily life is included to every field such as aerospaces.Conventional epoxy resin brittleness is big, poor toughness, thus impact resistant strength is poor,
In addition, the heat resisting temperature of epoxy resin is generally at 170 DEG C hereinafter, thus, in leading-edge fields such as aerospaces, its performance can't
It meets the requirements.High tenacity, heat-resist epoxy resin have urgent demand in field of compound material.
The toughness of epoxy resin can be improved to a certain extent using polysiloxane-grafted epoxy resin.Traditional grafting
The method of polysiloxanes be using reacted with active polysiloxanes (hydroxyl, amino, epoxy group etc.) with epoxy resin to be formed it is embedding
Section polymer improves the toughness of epoxy resin.As 103013048 A of Chinese patent CN is prepared for PGMA-PBMA-PDMS-
Five yuan of block copolymers of PBMA-PGMA, effectively raise the toughness of epoxy resin.But block polymer step is prepared
It is rapid cumbersome, while the poor heat resistance of polymer, thus its practical application is subject to certain restrictions.In addition, polysiloxanes and epoxy
The poor compatibility of resin, thus the stability of simple synthesis graft polymers is general, heat resistance is also poor.
Summary of the invention
The problem to be solved by the invention is to provide a kind of organic-silicon-modified epoxy resin, prepared contains POSS shell
Silicone-epoxy resin hydridization co-crosslinking structure there is the structure of heat-resisting POSS nanometer core and polymethylphenylsiloxane
Synergistic effect, can integrally improve the heat resistance of epoxy resin, in addition, the good flexibility of polysiloxanes can greatly improve and change
The toughness of property epoxy resin.
The present invention be solve the problems, such as it is set forth above used by technical solution be：
A kind of organic-silicon-modified epoxy resin, structural schematic diagram is as shown in Figure 1, preparation method is：Q is prepared first
The polymethylphenylsiloxane of type POSS sealing end, then the polymethylphenylsiloxane modified bisphenol A type ring oxygen blocked with Q type POSS
The silicone-epoxy resin hydridization co-crosslinking structure containing POSS shell is prepared in resin.With the poly- of methoxy-type POSS sealing end
For methyl phenyl siloxane, synthetic route is as shown in Figure 2.
Further, the preparation method of above-mentioned organic-silicon-modified epoxy resin is：The polymethyl-benzene base of Q type POSS sealing end
Siloxanes and epoxy resin are according to mass ratio 1:1-1:100 at 80-150 DEG C back flow reaction 6h or more, obtain organic-silicon-modified
Epoxy resin.
Further, the preparation method of the polymethylphenylsiloxane of the Q type POSS sealing end is：Terminal hydroxy group phenyl silicone oil
With Q type POSS according to mass ratio 1000:1 to 10:1 carries out back flow reaction 5h or more at 50-120 DEG C, obtains Q type POSS sealing end
Polymethylphenylsiloxane.
More specifically, the method that the present invention uses is the polymethylphenylsiloxane and asphalt mixtures modified by epoxy resin using Q type POSS sealing end
Rouge co-crosslinking prepares the epoxy resin of high heat resistance, high tenacity, and preparation method mainly includes following two step：
(1) Q type POSS blocks the preparation of polymethylphenylsiloxane
According to the mass fraction, POSS1 parts of Q type are taken, 10-1000 parts of terminal hydroxy group phenyl silicone oil (molecular weight 1000-100000),
It is to be mixed uniformly after, return stirring 5h or more (the general 5-20h) at 50-120 DEG C discharges after cooling, as Q type POSS sealing end
Polymethylphenylsiloxane；
(2) preparation of modifying epoxy resin by organosilicon
According to the mass fraction, the polymethylphenylsiloxane for taking the Q type POSS sealing end prepared in 1 part of step (1), is added warp
1-100 parts of bisphenol A type epoxy resin for crossing vacuum drying water removal, it is (general to be stirred at reflux 6h or more under conditions of 80-150 DEG C
6-20h), up to organic-silicon-modified epoxy resin after cooling.
According to the above scheme, the Q type POSS is the POSS with silicon tri-alkoxy group, structure and breviary structure table
It is as shown in Figure 3 up to formula.
According to the above scheme, the Q type POSS is the POSS containing silicon trimethoxy group or silicon triethoxy group
One of POSS etc. or more than one mixture, non-functional R2Group is methyl, vinyl, chloropropyl, aminopropyl, first
One of base acryloxypropyl etc. or more than one.
According to the above scheme, the bisphenol A type epoxy resin be epoxy resin E-21, E-31, E-35, E-39, E42, E-44,
One of E-51, E-54, E-55 etc. or more than one mixture.
Compared with prior art, the present invention prepares polymethylphenylsiloxane and bisphenol-A by the bridge linking effect of Q type POSS
The co-crosslinking structure of type epoxy resin, has the following advantages：
(1) POSS has good heat resistance as the smallest nanometer titanium dioxide silicon structure, is made by the bridging of POSS
With having " core " of the high-fire resistance being largely chemically bonded in the epoxy resin of preparation, the heat-resisting of modified resin can be greatly improved
Performance；
(2) polymethylphenylsiloxane is heat-resist, can be to epoxy by forming co-crosslinking structure with epoxy resin
The main chain of resin plays certain locking effect, thus can be further improved the heat resistance of epoxy resin；And polymethyl-benzene base silicon
The good flexibility of oxygen alkane segment can play the role of apparent toughening to epoxy resin；
(3) bridging that polymethylphenylsiloxane and epoxy resin pass through the POSS of polyfunctionality forms co-crosslinking structure,
The self aggregation of segment is difficult, thus whole stability is high；
(4) synthesis only includes that two steps are heated at reflux process, and preparation process is simple, high-efficient.
Detailed description of the invention
Fig. 1 is modifying epoxy resin by organosilicon structural schematic diagram；
Fig. 2 is the synthetic method of modifying epoxy resin by organosilicon；
Fig. 3 is the chemical structure and its breviary expression structural formula of Q type POSS.
Specific embodiment
For a better understanding of the present invention, below with reference to the embodiment content that the present invention is furture elucidated, but the present invention is not
It is limited only to the following examples.
Embodiment 1
A kind of preparation method of organic-silicon-modified epoxy resin, specific step is as follows：
1) it takes eight (trimethoxy silica ethyl) POSS 1g in three-necked flask, to connect thermometer and condensation reflux unit, adds
The terminal hydroxy group phenyl silicone oil for entering 10g molecular weight 1000, is stirred at reflux 20h at 50 DEG C, obtains thick liquid, as Q type POSS
The polymethylphenylsiloxane of sealing end；
2) thick liquid 1g after cooling is taken, is added and passes through vacuum drying epoxy resin E-44 100g, at 150 DEG C
Under the conditions of be stirred at reflux 10h, it is cooling after to get arriving modifying epoxy resin by organosilicon.
Embodiment 2
A kind of preparation method of organic-silicon-modified epoxy resin, specific step is as follows：
1) it takes six (vinyl) two (triethoxy silica ethyl) POSS1g in three-necked flask, connect thermometer and is condensed back to
Device is flowed, the terminal hydroxy group phenyl silicone oil of 100g molecular weight 10000 is added, is stirred at reflux 10h at 80 DEG C, obtains thick liquid,
The polymethylphenylsiloxane of as Q type POSS sealing end；
2) thick liquid 1g after cooling is taken, is added and passes through vacuum drying epoxy resin E-21 100g, in 90 DEG C of item
It is stirred at reflux 8h under part, arrives modifying epoxy resin by organosilicon after cooling.
Embodiment 3
A kind of preparation method of organic-silicon-modified epoxy resin, specific step is as follows：
1) four (methyl) four (triethoxysilicane methyl) POSS1g is taken in three-necked flask, to connect thermometer and condensing reflux
Device is added the terminal hydroxy group phenyl silicone oil of 500g molecular weight 5000, is stirred at reflux 10h at 80 DEG C, obtains thick liquid, as
The polymethylphenylsiloxane of Q type POSS sealing end；
2) thick liquid 1g after cooling is taken, is added and passes through vacuum drying epoxy resin E-21 100g, in 90 DEG C of item
It is stirred at reflux 8h under part, arrives modifying epoxy resin by organosilicon after cooling.
Embodiment 4
A kind of preparation method of organic-silicon-modified epoxy resin, specific step is as follows：
1) it takes four (aminopropyl) four (trimethoxy silicon methyl) POSS1g in three-necked flask, connect thermometer and is condensed back to
Device is flowed, the terminal hydroxy group phenyl silicone oil of 1000g molecular weight 100000 is added, is stirred at reflux 5h at 120 DEG C, obtains viscous fluid
The polymethylphenylsiloxane of body, as Q type POSS sealing end；
2) thick liquid 10g after cooling is taken, is added and passes through vacuum drying epoxy resin E-31 10g, at 150 DEG C
Under the conditions of be stirred at reflux 6h, it is cooling after to get arriving modifying epoxy resin by organosilicon.
Embodiment 5
A kind of preparation method of organic-silicon-modified epoxy resin, specific step is as follows：
1) it takes four (chloropropyl) four (trimethoxy silicon methyl) POSS1g in three-necked flask, connect thermometer and is condensed back to
Device is flowed, the terminal hydroxy group phenyl silicone oil of 1000g molecular weight 100000 is added, is stirred at reflux 7.5h at 100 DEG C, obtains viscous fluid
The polymethylphenylsiloxane of body, as Q type POSS sealing end；
2) thick liquid 1g after cooling is taken, is added and passes through vacuum drying epoxy resin E-35 50g, in 80 DEG C of item
It is stirred at reflux 20h under part, arrives modifying epoxy resin by organosilicon after cooling.
Embodiment 6
A kind of preparation method of organic-silicon-modified epoxy resin, specific step is as follows：
1) four (chloropropyl) four (trimethoxy silicon methyl) POSS0.5g are taken, six (methacryloxypropyl) two (three
Ethyoxyl silicon methyl) POSS0.5g in three-necked flask, connects thermometer and condensation reflux unit, 100g molecular weight is added
50000 terminal hydroxy group phenyl silicone oil, is stirred at reflux 6h at 120 DEG C, obtains thick liquid, the poly- first of as Q type POSS sealing end
Base phenyl siloxane；
2) thick liquid 1g after cooling is taken, is added and passes through vacuum drying epoxy resin E-39 75g, in 120 DEG C of item
It is stirred at reflux 10h under part, arrives modifying epoxy resin by organosilicon after cooling.
Embodiment 7
A kind of preparation method of organic-silicon-modified epoxy resin, specific step is as follows：
1) it takes six (aminopropyl) two (triethoxysilicane methyl) POSS1g in three-necked flask, connect thermometer and is condensed back to
Device is flowed, the terminal hydroxy group phenyl silicone oil of 100g molecular weight 50000 is added, is stirred at reflux 6h at 120 DEG C, obtains thick liquid,
The polymethylphenylsiloxane of as Q type POSS sealing end；
2) thick liquid 1g after cooling is taken, is added and exists by vacuum drying epoxy resin E-42 75g, E-51 25g
It is stirred at reflux 10h under conditions of 120 DEG C, arrives modifying epoxy resin by organosilicon after cooling.
Embodiment 8
A kind of preparation method of organic-silicon-modified epoxy resin, specific step is as follows：
1) it takes six (aminopropyl) two (triethoxysilicane methyl) POSS1g in three-necked flask, connect thermometer and is condensed back to
Device is flowed, the terminal hydroxy group phenyl silicone oil of 100g molecular weight 50000 is added, is stirred at reflux 6h at 120 DEG C, obtains thick liquid,
The polymethylphenylsiloxane of as Q type POSS sealing end；
2) thick liquid 1g after cooling is taken, is added and exists by vacuum drying epoxy resin E-54 50g, E-55 50g
It is stirred at reflux 10h under conditions of 120 DEG C, arrives modifying epoxy resin by organosilicon after cooling.
Comparative example 1
It takes prestox POSS1g in three-necked flask, connects thermometer and condensation reflux unit, 100g molecular weight is added
50000 terminal hydroxy group phenyl silicone oil, is stirred at reflux 6h at 120 DEG C, obtains thick liquid；Thick liquid 1g after cooling is taken,
It is added and is stirred at reflux 10h under conditions of 120 DEG C by vacuum drying epoxy resin E-54 50g, E-55 50g, after cooling,
Obtain modified epoxy.
Comparative example 2
By the terminal hydroxy group phenyl silicone oil of 100g molecular weight 50000, it is stirred at reflux 6h at 120 DEG C, obtains thick liquid；It takes
Thick liquid 1g after cooling is added by vacuum drying epoxy resin E-54 50g, E-55 50g under conditions of 120 DEG C
It is stirred at reflux 10h and obtains modified epoxy after cooling.
Comparative example 3
It directly takes and is stirred at reflux under conditions of 120 DEG C by vacuum drying epoxy resin E-54 50g, E-55 50g
10h carries out the comparative experiments of next step after cooling.
Modified epoxy or epoxy resin prepared by above-described embodiment 1-8 and comparative example 1-3 are taken, is worked as according to epoxy
Amount is added curing agent and promotor and carries out staged curing preparing epoxy resin induration (curing agent being according to epoxy in cured condition
Equivalent calculates, and accelerator dosage is the 5% of amount of resin), the stretching under different temperatures is then measured according to GB 7124-2008
Shear strength measures different temperatures tensile strength and elongation at break according to the method for GB T 1701-2001, uses thermogravimetry
(nitrogen atmosphere, 10 DEG C of heating rate is per minute) measurement 5% weightless temperature of induration, according to GB T 1843-2008, its measurement is anti-
Impact strength.The test result of epoxy resin induration is as shown in table 1.
Table 1
As it can be seen from table 1 by organic-silicon-modified epoxy resin, shear strength and tensile strength and common bisphenol-A
Epoxy resin is close or slightly higher, and room temperature elongation at break, high temperature fracture elongation are significantly improved, and impact strength is obvious
It improves, thermal decomposition temperature significantly improves, illustrates that bisphenol-A epoxy can be significantly improved using the method modifying epoxy resin by organosilicon
The toughness and heat resistance of resin, reason is that the chemical graft of organosilicon radical substantially increases the toughness of resin, and POSS
The access of group then improves the heat resistance of material, in addition, the heat resistance of silicone segments is also very good, it is resistance to the entirety of material
Apparent facilitation is played in hot raising.The POSS of comparative example 1 be it is inactive, can not be reacted with epoxy resin, and this
The embodiment of invention is to be bridged epoxy resin and organosilicon by active POSS；Comparative example 2 and 3 also cannot achieve ring
Effective bridge joint of oxygen resin and organosilicon.
Therefore, the present invention improves the toughness and heat resistance of epoxy resin simultaneously, also has bonding force is strong, tensile strength is high etc.
Advantage, obtained epoxy resin can be applied in fields such as composite material, aerospace, high-end LED encapsulation.
The above is only a preferred embodiment of the present invention, it is noted that come for those of ordinary skill in the art
It says, without departing from the concept of the premise of the invention, several modifications and variations can also be made, these belong to of the invention
Protection scope.
Claims (8)
1. a kind of organic-silicon-modified epoxy resin, it is characterised in that it passes through the polymethylphenylsiloxane of Q type POSS sealing end
Modified bisphenol A type epoxy resin is prepared；The polymethylphenylsiloxane of Q type POSS sealing end is terminal hydroxy group phenyl silicone oil and Q
Type POSS reaction gained.
2. a kind of organic-silicon-modified epoxy resin according to claim 1, it is characterised in that the Q type POSS is with silicon
The POSS of oxygen silicon tri-alkoxy group, structure is as shown in Equation 1, wherein R1For CH3Or CH2CH3, R2For methyl, ethyl, ethylene
One of base, chloropropyl, aminopropyl, methacryloxypropyl or more than one.
3. a kind of preparation method of organic-silicon-modified epoxy resin, it is characterised in that the polymethyl-benzene base for blocking Q type POSS
Siloxanes and epoxy resin are according to mass ratio 1:1-1:100 at 80-150 DEG C back flow reaction 6h or more change to get to organosilicon
The epoxy resin of property.
4. the preparation method of the organic-silicon-modified epoxy resin of one kind according to claim 3, it is characterised in that the Q type
The preparation method of polymethylphenylsiloxane of POSS sealing end is：Terminal hydroxy group phenyl silicone oil and Q type POSS are according to mass ratio 1000:
1 to 10:1 carries out back flow reaction 5h or more at 50-120 DEG C, obtains the polymethylphenylsiloxane of Q type POSS sealing end.
5. a kind of preparation method of organic-silicon-modified epoxy resin, it is characterised in that mainly include following two step：
(1) Q type POSS blocks the preparation of polymethylphenylsiloxane
According to the mass fraction, take POSS1 parts of Q type, 10-1000 parts of terminal hydroxy group phenyl silicone oil, it is to be mixed uniformly after, at 50-120 DEG C
Lower return stirring 5h or more discharges after cooling, the polymethylphenylsiloxane of as Q type POSS sealing end；
(2) preparation of modifying epoxy resin by organosilicon
According to the mass fraction, the polymethylphenylsiloxane for taking the Q type POSS sealing end prepared in 1 part of step (1), is added by true
1-100 parts of bisphenol A type epoxy resin of the dry water removal of sky are stirred at reflux 6h or more under conditions of 80-150 DEG C, are after cooling
Obtain organic-silicon-modified epoxy resin.
6. the preparation method of the organic-silicon-modified epoxy resin of one kind according to claim 5, it is characterised in that the Q type
POSS is the POSS with silicon oxygen silicon tri-alkoxy group, and structure is as shown in Equation 1, wherein R1For CH3Or CH2CH3, R2For first
One of base, ethyl, vinyl, chloropropyl, aminopropyl, methacryloxypropyl or more than one.
7. the preparation method of the organic-silicon-modified epoxy resin of one kind according to claim 5, it is characterised in that the Q type
POSS is one of POSS of the POSS containing silicon trimethoxy group or silicon triethoxy group or more than one mixing
Object.
8. the preparation method of the organic-silicon-modified epoxy resin of one kind according to claim 5, it is characterised in that described double
Phenol A type epoxy resin be epoxy resin E-21, E-31, E-35, E-39, E42, E-44, E-51, E-54, one of E-55 or
More than one mixture.
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| CN109749083A (en) * | 2018-12-10 | 2019-05-14 | 沈阳化工大学 | Eight (trimethoxy silica ethyl) poss silicone rubber crosslinking agent |
| CN113004704A (en) * | 2021-04-01 | 2021-06-22 | 湖北航泰科技有限公司 | Silicon rubber, preparation method thereof and silicon rubber elastic part |
| CN113082783A (en) * | 2020-01-08 | 2021-07-09 | 万华化学集团股份有限公司 | Silicone branched polymer, preparation method thereof and defoaming agent composition comprising same |
| CN113637446A (en) * | 2021-09-07 | 2021-11-12 | 广州市白云化工实业有限公司 | High-strength silane modified polyether adhesive and preparation method thereof |
| CN114591598A (en) * | 2022-03-13 | 2022-06-07 | 连云港华海诚科电子材料有限公司 | Liquid plastic package material for wafer level packaging and preparation method thereof |
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| CN113082783A (en) * | 2020-01-08 | 2021-07-09 | 万华化学集团股份有限公司 | Silicone branched polymer, preparation method thereof and defoaming agent composition comprising same |
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| CN113637446B (en) * | 2021-09-07 | 2023-01-03 | 广州市白云化工实业有限公司 | High-strength silane modified polyether adhesive and preparation method thereof |
| CN114591598A (en) * | 2022-03-13 | 2022-06-07 | 连云港华海诚科电子材料有限公司 | Liquid plastic package material for wafer level packaging and preparation method thereof |
| CN114591598B (en) * | 2022-03-13 | 2023-06-02 | 连云港华海诚科电子材料有限公司 | Liquid plastic package material for wafer level package and preparation method thereof |
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