CN110330763A - A kind of high-fire resistance epoxy resin and preparation method thereof - Google Patents
A kind of high-fire resistance epoxy resin and preparation method thereof Download PDFInfo
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- CN110330763A CN110330763A CN201910275939.1A CN201910275939A CN110330763A CN 110330763 A CN110330763 A CN 110330763A CN 201910275939 A CN201910275939 A CN 201910275939A CN 110330763 A CN110330763 A CN 110330763A
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- epoxy
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/20—Polysulfones
- C08G75/23—Polyethersulfones
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/06—Polysulfones; Polyethersulfones
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/04—Polymer mixtures characterised by other features containing interpenetrating networks
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- Epoxy Resins (AREA)
Abstract
The present invention relates to epoxy resin of a kind of high-fire resistance and preparation method thereof, it is obtained after cooperating bisphenol A type epoxy resin solidification by epoxy-capped modified oligomeric polyether sulfone, by the way that high-fire resistance and the preferable polyether sulfone structure of flexibility are introduced epoxy main chains, greatly improve the heat resistance and flexibility of epoxy resin, obtained epoxy resin has the characteristics that viscosity is low, heat-resist flexibility is high, can be widely applied for the carbon fibre composite field of high-fire resistance high-flexibility requirement.
Description
Technical field
The present invention relates to a kind of high-fire resistance epoxy resin and preparation method thereof, belong to macromolecule fine chemical technology neck
Domain.
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.
The heat distortion temperature of conventional epoxy is usually no more than 120 DEG C, it is difficult to meet the fields such as aerospace to carbon fiber
Tie up the requirement of composite material.The heat resistance that epoxy resin can be significantly improved by the modification of thermoplastic engineering plastic, mentions simultaneously
Its high toughness, expands the application range of epoxy resin significantly.However, conventional engineering plastics and epoxy resin compatibility are poor,
It cannot be used and being easy to produce and mutually separate by being simply blended；The viscosity that resin can be then significantly improved by graft modification, because
And it is difficult to meet the craftsmanship that molding needs.
Summary of the invention
The technical problem to be solved by the present invention is to provide a kind of high heat resistance in view of the deficiency of the prior art
Property epoxy resin by the way that high-fire resistance and the preferable polyether sulfone structure of flexibility are introduced epoxy main chains greatly improve ring
The heat resistance and flexibility of oxygen resin, obtained epoxy resin have the characteristics that viscosity is low, heat-resist flexibility is high.
The present invention be solve the problems, such as it is set forth above used by technical solution are as follows:
A kind of modified epoxy of high-fire resistance, by epoxy-capped modified oligomeric polyether sulfone and bisphenol type epoxy tree
Rouge mixing gained；Wherein, the quality of epoxy-capped modified oligomeric polyether sulfone and bisphenol A type epoxy resin than range be 0.25~
1.5。
According to the above scheme, epoxy-capped modified oligomeric polyether sulfone is the chemical combination that main chain contains epoxy group and polyether sulfone structure
Object, chemical structure is as shown in Equation 1, polymerization degree n 5-10.
According to the above scheme, the epoxy-capped modified oligomeric polyether sulfone the preparation method comprises the following steps: by hydroxy-end capped oligomeric poly-
Ether sulfone and epoxychloropropane carry out condensation reaction under KOH effect, obtain using neutralization, precipitating, washing, and reaction schematic diagram is such as
Shown in Fig. 1.Wherein, the mass ratio of hydroxy-end capped the oligomeric polyether sulfone and epoxychloropropane is 4.5~5.5,40wt%
The dosage of KOH be hydroxy-end capped oligomeric polyether sulfone quality 0.35~0.45, with ethanol solution (volume fraction 90%~
It 95%) is solvent, the reaction condition is that temperature rising reflux stirs 4.5~5.5h.
Further, the hydroxy-end capped oligomeric polyether sulfone, chemical structure is as shown in Equation 2, polymerization degree n 5-
10。
Further, the hydroxy-end capped oligomeric polyether sulfone the preparation method comprises the following steps: by bisphenol-A and 4,4 '-dichloros
Sulfone with ethanol water (volume fraction 90%~95%) be solvent, KOH effect under control condensation reaction, using neutralize,
Precipitating, washing obtain, and reaction schematic diagram is as shown in Figure 2.Wherein, the molar ratio of the bisphenol-A and 4,4 '-dichloro diphenyl sulfones exists
In 1.4~1.2 ranges, the dosage of KOH is 1.8~2.2 times of 4,4 '-dichloro diphenyl sulfone moles, and the reaction condition is
Heating stirring 5h is continued to after being warming up to reflux.
According to the above scheme, the bisphenol A type epoxy resin is epoxy resin E-21, E-31, E-35, E-39, E42, E-
One of 44, E-51, E-54, E-56 etc. or more than one mixture.
Compared with prior art, the beneficial effects of the present invention are:
(1) the oligomeric polyether sulfone being modified to epoxy resin in high-fire resistance epoxy resin of the present invention is epoxy
Sealing end, can be improved the compatibility of polyether sulfone and epoxy resin, solves the manufacturability issues of composite epoxy resin；
(2) high-fire resistance epoxy resin of the present invention forms interpenetrating networks knot by the polyether sulfone and epoxy resin introduced
Structure, the toughness and heat resistance of Lai Tigao epoxy resin, the inierpeneirating network structure of formation is while raising cross linking of epoxy resin is spent
The average molecular weight between crosslinking points is not reduced, improves the toughness of epoxy resin；
(3) high-fire resistance epoxy resin of the present invention is passed through by the mutual winding between polyether sulfone and epoxy resin segment
It wears and achievees the purpose that reduce resin segment heat sensitivity, while the introducing of the heat-resisting segment of polyether sulfone greatly improves the heat-resisting of material
Property.
Detailed description of the invention
Fig. 1 is epoxy-capped modified oligomeric polyether sulfone synthetic reaction schematic diagram；
Fig. 2 is hydroxy-end capped oligomeric polyether sulfone synthesis schematic diagram.
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 high-fire resistance epoxy resin, the specific steps are as follows:
(1) hydroxy-end capped oligomeric polyether sulfone is prepared
It is to be added in 90% ethyl alcohol that 4mol bisphenol-A and 4,4 '-dichloro diphenyl sulfone of 3mol, which are dissolved in 2000g volume fraction,
5.4molKOH after return stirring reacts 5h, adds excessive HCl and neutralizes, and is subsequently added into 2000g distilled water to Precipitation, analysis
Dry, as hydroxy-end capped oligomeric polyether sulfone after washing, the washing of 50% ethanol water, the degree of polymerization 6 are precipitated out；
(2) epoxy-capped modified oligomeric polyether sulfone is prepared
Oligomeric polyether sulfone hydroxy-end capped obtained in 50g step (1) is dissolved in the ethyl alcohol that 200g volume fraction is 95%
In, 20g 40wt%KOH aqueous solution is added, 10g epoxychloropropane is added dropwise under return stirring in 2h, subsequent continuous reaction completely is added dropwise
After 5h, 10g concentrated hydrochloric acid is added, 1000g water is subsequently added into Precipitation, it is water-soluble by washing, 50% ethyl alcohol that precipitating is precipitated
Dry, as epoxy-capped modified oligomeric polyether sulfone, the degree of polymerization 6 after liquid washing.
(3) blending epoxy is prepared
Epoxy-capped modified oligomeric polyether sulfone obtained in 20g (2) is dissolved in 80g bisphenol A type epoxy resin E-51, i.e.,
Obtain blending epoxy, as high-fire resistance epoxy resin.
Embodiment 2
A kind of preparation method of high-fire resistance epoxy resin, the specific steps are as follows:
(1) hydroxy-end capped oligomeric polyether sulfone is prepared
By 5mol bisphenol-A and 4mol4, it is to be added in 95% ethyl alcohol that 4 '-dichloro diphenyl sulfones, which are dissolved in 2000g volume fraction,
After excess HCl neutralization is added after 8molKOH, return stirring reaction 4.5h, 2000g distilled water is added to Precipitation, is precipitated and sinks
Form sediment dry, as hydroxy-end capped oligomeric polyether sulfone after washing, the washing of 50% ethanol water, the degree of polymerization 8；
(2) epoxy-capped modified oligomeric polyether sulfone is prepared
It is to be added in 95% ethyl alcohol that oligomeric polyether sulfone hydroxy-end capped obtained in 50g (1), which is dissolved in 200g volume fraction,
10g epoxychloropropane is added dropwise under return stirring for 17.5g 40wt%KOH aqueous solution in 2h, after subsequent continuous reaction 5h completely is added dropwise
10g concentrated hydrochloric acid is added, 1000g water is added to Precipitation, precipitating is precipitated and is done after washing, the washing of 50% ethanol water
It is dry, as epoxy-capped modified oligomeric polyether sulfone, the degree of polymerization 8；
(3) blending epoxy is prepared
To get blending epoxy, i.e., epoxy-capped modified oligomeric polyether sulfone obtained in 20g (2) is dissolved in 80gE-44
For high-fire resistance epoxy resin.
Embodiment 3
A kind of preparation method of high-fire resistance epoxy resin, the specific steps are as follows:
(1) hydroxy-end capped oligomeric polyether sulfone is prepared
By 6mol bisphenol-A and 5mol4, it is to be added in 90% ethyl alcohol that 4 '-dichloro diphenyl sulfones, which are dissolved in 2000g volume fraction,
After excess HCl neutralization is added after 11molKOH, return stirring reaction 5.5h, 2000g distilled water is added to Precipitation, is precipitated and sinks
Form sediment dry, as hydroxy-end capped oligomeric polyether sulfone after washing, the washing of 50% ethanol water, the degree of polymerization 10；
(2) epoxy-capped modified oligomeric polyether sulfone is prepared
It is to be added in 95% ethyl alcohol that oligomeric polyether sulfone hydroxy-end capped obtained in 50g (1), which is dissolved in 200g volume fraction,
10g epoxychloropropane is added dropwise under return stirring for 20g40wt%KOH aqueous solution in 2h, be added after subsequent continuous reaction 5h completely is added dropwise
1000g water is added to Precipitation in 10g concentrated hydrochloric acid, and precipitation precipitating is dry after washing, the washing of 50% ethanol water, i.e.,
For epoxy-capped modified oligomeric polyether sulfone, the degree of polymerization 10；
(3) blending epoxy is prepared
To get blending epoxy, i.e., epoxy-capped modified oligomeric polyether sulfone obtained in 30g (2) is dissolved in 70gE-56
For high-fire resistance epoxy resin.
Embodiment 4
A kind of preparation method of high-fire resistance epoxy resin, the specific steps are as follows:
(1) hydroxy-end capped oligomeric polyether sulfone is prepared
By 4mol bisphenol-A and 3mol4,4 '-dichloro diphenyl sulfones are dissolved in 90% ethyl alcohol of 2000g volume fraction, are added
After excess HCl neutralization is added after 6molKOH, return stirring reaction 5h, 2000g distilled water is added to Precipitation, is precipitated and precipitates
Dry, as hydroxy-end capped oligomeric polyether sulfone, the degree of polymerization 6 after washing, the washing of 50% ethanol water；
(2) epoxy-capped modified poly (ether-sulfone) is prepared
It is to be added in 90% ethyl alcohol that oligomeric polyether sulfone hydroxy-end capped obtained in 50g (1), which is dissolved in 200g volume fraction,
10g epoxychloropropane is added dropwise under return stirring for 22.5g 40wt%KOH aqueous solution in 2h, after subsequent continuous reaction 5h completely is added dropwise
10g concentrated hydrochloric acid is added, 1000g water is added to Precipitation, precipitating is precipitated and is done after washing, the washing of 50% ethanol water
It is dry, as epoxy-capped modified oligomeric polyether sulfone, the degree of polymerization 6；
(3) blending epoxy is prepared
To get blending epoxy, i.e., epoxy-capped modified oligomeric polyether sulfone obtained in 50g (2) is dissolved in 50gE-54
For high-fire resistance epoxy resin.
Embodiment 5
A kind of preparation method of high-fire resistance epoxy resin, the specific steps are as follows:
(1) hydroxy-end capped oligomeric polyether sulfone is prepared
By 5mol bisphenol-A and 4mol4, it is to be added in 90% ethyl alcohol that 4 '-dichloro diphenyl sulfones, which are dissolved in 2000g volume fraction,
After excess HCl neutralization is added after 8molKOH, return stirring reaction 5h, 2000g distilled water is added to Precipitation, is precipitated and precipitates
Dry, as hydroxy-end capped oligomeric polyether sulfone, the degree of polymerization 8 after washing, the washing of 50% ethanol water；
(2) epoxy-capped modified poly (ether-sulfone) is prepared
It is to be added in 95% ethyl alcohol that oligomeric polyether sulfone hydroxy-end capped obtained in 50g (1), which is dissolved in 200g volume fraction,
10g epoxychloropropane is added dropwise under return stirring for 20g40wt%KOH aqueous solution in 2h, be added after subsequent continuous reaction 5h completely is added dropwise
1000g water is added to Precipitation in 10g concentrated hydrochloric acid, and precipitation precipitating is dry after washing, the washing of 50% ethanol water, i.e.,
For epoxy-capped modified oligomeric polyether sulfone, the degree of polymerization 8；
(3) blending epoxy is prepared
Epoxy-capped modified oligomeric polyether sulfone obtained in 60g (2) is dissolved in the mixture of 20gE-56 and 20gE-20, i.e.,
Obtain blending epoxy, as high-fire resistance epoxy resin.
Embodiment 6
A kind of preparation method of high-fire resistance epoxy resin, the specific steps are as follows:
(1) hydroxy-end capped oligomeric polyether sulfone is prepared
By 5mol bisphenol-A and 4mol4, it is to be added in 90% ethyl alcohol that 4 '-dichloro diphenyl sulfones, which are dissolved in 2000g volume fraction,
After excess HCl neutralization is added after 8molKOH, return stirring reaction 5h, 2000g distilled water is added to Precipitation, is precipitated and precipitates
Dry, as hydroxy-end capped oligomeric polyether sulfone, the degree of polymerization 8 after washing, the washing of 50% ethanol water
(2) epoxy-capped modified poly (ether-sulfone) is prepared
It is to be added in 95% ethyl alcohol that oligomeric polyether sulfone hydroxy-end capped obtained in 50g (1), which is dissolved in 200g volume fraction,
10g epoxychloropropane is added dropwise under return stirring for 20g4wt0%KOH aqueous solution in 2h, be added after subsequent continuous reaction 5h completely is added dropwise
1000g water is added to Precipitation in 10g concentrated hydrochloric acid, and precipitation precipitating is dry after washing, the washing of 50% ethanol water, i.e.,
For epoxy-capped modified oligomeric polyether sulfone, the degree of polymerization 8.
(3) blending epoxy is prepared
Epoxy-capped modified oligomeric polyether sulfone obtained in 50g (2) is dissolved in the mixture of 30gE-56 and 20gE-39, i.e.,
Obtain blending epoxy, as high-fire resistance epoxy resin.
Comparative example 1
Directly use E-56 as matrix resin.
Comparative example 2
Directly use E-20 as matrix resin.
Comparative example 3
Use the mixed resin of 20gE-56 and 20gE-20 as matrix resin.
Matrix resin described in the high-fire resistance epoxy resin and comparative example 1-3 for taking above-described embodiment 1-8 to prepare, according to ring
Oxygen equivalent is added curing agent (m-phenylene diamine (MPD)) and promotor (DMP-30) and carries out staged curing preparing asphalt mixtures modified by epoxy resin in cured condition
Rouge induration (curing agent is calculated according to epoxide equivalent, and accelerator dosage is the 5% of amount of resin, mass fraction), according to GB/T
Then viscosity when 22235 measurement epoxy resin initial mixing measures the drawing under different temperatures according to GB 7124-2008
Shear strength is stretched, different temperatures tensile strength and elongation at break is measured according to the method for GB T 1701-2001, uses thermogravimetric
Method (nitrogen atmosphere, 10 DEG C of heating rate is per minute) measurement 5% weightless temperature of induration, according to its survey of GB T 1843- 2008
Determine 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 can obviously be mentioned using epoxy-capped modified oligomeric polyether sulfone and bisphenol A epoxide resin cooperation
The heat resistance of high epoxy resin, while its toughness and intensity also have a certain upgrade.Therefore, the present invention can significantly improve bis-phenol
The heat resistance of A epoxy resin also has many advantages, such as strong operability, and Technological adaptability is good, and obtained epoxy resin can be multiple
The fields such as condensation material, aerospace, high-end LED encapsulation are applied.
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 modified epoxy of high-fire resistance, it is characterised in that it is by epoxy-capped modified oligomeric polyether sulfone and bisphenol-A
Type epoxy resin mixing gained；Wherein, the mass ratio of epoxy-capped modified oligomeric polyether sulfone and bisphenol A type epoxy resin is 0.25
~1.5.
2. a kind of modified epoxy of high-fire resistance according to claim 1, it is characterised in that described is epoxy-capped
Modified oligomeric polyether sulfone is the compound that main chain contains epoxy group and polyether sulfone structure, and chemical structure is as shown in Equation 1, polymerization
Degree n is 5-10.
3. a kind of modified epoxy of high-fire resistance according to claim 1, it is characterised in that described epoxy-capped to change
Property oligomeric polyether sulfone the preparation method comprises the following steps: hydroxy-end capped oligomeric polyether sulfone and epoxychloropropane is condensed under KOH effect
Reaction, obtains epoxy-capped modified oligomeric polyether sulfone using neutralization, precipitating, washing.
4. a kind of modified epoxy of high-fire resistance according to claim 3, it is characterised in that described hydroxy-end capped
The dosage that the mass ratio of oligomeric polyether sulfone and epoxychloropropane is 4.5~5.5,30-50wt%KOH is hydroxy-end capped oligomeric
The 0.35~0.45 of polyether sulfone quality, using 90%~95% ethanol solution of volume fraction as solvent, the reaction condition is heating
4.5~5.5h of return stirring.
5. a kind of modified epoxy of high-fire resistance according to claim 3 or 4, it is characterised in that the hydroxyl envelope
The oligomeric polyether sulfone at end, chemical structure is as shown in Equation 2, polymerization degree n 5-10.
6. a kind of modified epoxy of high-fire resistance according to claim 3 or 4, it is characterised in that described hydroxy-end capped
Oligomeric polyether sulfone the preparation method comprises the following steps: bisphenol-A and 4,4 '-dichloro diphenyl sulfones are using ethanol water as solvent, under KOH effect
Condensation reaction is controlled, obtains hydroxy-end capped oligomeric polyether sulfone using neutralization, precipitating, washing.
7. a kind of modified epoxy of high-fire resistance according to claim 6, it is characterised in that the bisphenol-A and 4,
For the molar ratio of 4 '-dichloro diphenyl sulfones in 1.4~1.2 ranges, the dosage of KOH is the 1.8 of 4,4 '-dichloro diphenyl sulfone moles
~2.2 times, the reaction condition is to continue to heating stirring 4-6h after being warming up to reflux.
8. a kind of modified epoxy of high-fire resistance described according to claim 1 or 6 or 7, it is characterised in that bisphenol-A type ring
Oxygen resin be epoxy resin E-21, E-31, E-35, E-39, E42, E-44, E-51, E-54, one of E-56 or more than one
Mixture.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114249895A (en) * | 2021-11-19 | 2022-03-29 | 兰溪聪普新材料有限公司 | Long-chain hydroxyl-free sulfone ether epoxy resin and preparation method thereof |
| CN114395215A (en) * | 2021-12-20 | 2022-04-26 | 兰溪聪普新材料有限公司 | Sulfone ether epoxy adhesive and UHMWPE fiber reinforced bulletproof composite material and preparation method thereof |
| CN116285231A (en) * | 2023-05-18 | 2023-06-23 | 东方飞源(山东)电子材料有限公司 | Electronic-grade copper-clad plate resin and preparation method thereof |
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| CN107746549A (en) * | 2017-11-08 | 2018-03-02 | 威海光威复合材料股份有限公司 | bisphenol A type epoxy resin and preparation method thereof |
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| CN107746549A (en) * | 2017-11-08 | 2018-03-02 | 威海光威复合材料股份有限公司 | bisphenol A type epoxy resin and preparation method thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114249895A (en) * | 2021-11-19 | 2022-03-29 | 兰溪聪普新材料有限公司 | Long-chain hydroxyl-free sulfone ether epoxy resin and preparation method thereof |
| CN114395215A (en) * | 2021-12-20 | 2022-04-26 | 兰溪聪普新材料有限公司 | Sulfone ether epoxy adhesive and UHMWPE fiber reinforced bulletproof composite material and preparation method thereof |
| CN116285231A (en) * | 2023-05-18 | 2023-06-23 | 东方飞源(山东)电子材料有限公司 | Electronic-grade copper-clad plate resin and preparation method thereof |
| CN116285231B (en) * | 2023-05-18 | 2023-08-29 | 东方飞源(山东)电子材料有限公司 | Electronic-grade copper-clad plate resin and preparation method thereof |
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Application publication date: 20191015 |