CN114133535A - Moisture-heat-resistant epoxy resin and preparation method and application thereof - Google Patents
Moisture-heat-resistant epoxy resin and preparation method and application thereof Download PDFInfo
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- CN114133535A CN114133535A CN202111615705.0A CN202111615705A CN114133535A CN 114133535 A CN114133535 A CN 114133535A CN 202111615705 A CN202111615705 A CN 202111615705A CN 114133535 A CN114133535 A CN 114133535A
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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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/3218—Carbocyclic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
- C07D303/23—Oxiranylmethyl ethers of compounds having one hydroxy group bound to a six-membered aromatic ring, the oxiranylmethyl radical not being further substituted, i.e.
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Abstract
The invention provides a moisture-heat resistant epoxy resin and a preparation method and application thereof, belonging to the technical field of epoxy resins. The epoxy resin provided by the invention has a 3-functional group structure, the whole molecular chain does not contain polar groups such as hydroxyl groups and the like, the adsorption effect of the epoxy resin on water is weakened from the angle of the structure of the epoxy resin, the reduction of the physical and chemical properties of a resin cured product caused by poor moisture resistance is prevented, after the epoxy resin is mixed and cured with 4, 4' -diaminodiphenyl sulfone (DDS), the saturated water absorption rate is obviously reduced, and the problem that the polar groups in the epoxy resin easily absorb water is solved. The epoxy resin molecular structure provided by the invention has a 3-functional group structure, and the formed epoxy resin condensate has the characteristics of high crosslinking density, low water absorption and excellent processability, has remarkable humidity and heat resistance, and is particularly suitable for the field of microelectronic packaging.
Description
Technical Field
The invention relates to the technical field of epoxy resin, in particular to a moisture-heat-resistant epoxy resin and a preparation method and application thereof.
Background
Epoxy resin is widely applied to the packaging fields of semiconductor devices, integrated circuits, consumer electronics, automobiles, aerospace, military and the like as a packaging material, basically occupies more than 97% of the microelectronic packaging material market due to the advantages of excellent electrical insulation, low cost, simple process and the like, and the reliability, stability and service life of the microelectronic packaging effect are directly determined by the performance of the epoxy resin. And the wet heat resistance of the epoxy resin is still a short plate in all properties. The data show that every 1% increase in water absorption of the cured resin lowers its Tg by 20-25 ℃.
The resin composition and structure determine the absorption and diffusion behavior of water in the matrix resin. For polymers, polar groups in the molecular structure have excellent affinity for water, which is a key factor that hinders the resistance to moist heat. Obviously, the moisture and heat resistance of the general epoxy resin cannot meet the application in high-end fields all the time due to the large amount of polar hydroxyl contained in the general epoxy resin.
In order to improve the moisture and heat resistance of epoxy resin, the mainstream methods of the industry include: 1) when the epoxy resin is cured by the modified curing agent, part of groups react with the hydroxyl groups of the epoxy resin, so that part of the hydroxyl groups are eliminated, the proportion of polar groups in a system is reduced, and the water absorption rate can be effectively reduced; 2) by nanoparticles such as: particles such as lipophilic nano silicon dioxide or organic nano montmorillonite are filled in the cavity inside the matrix resin to reduce the water absorption; 3) by modifying the epoxy resin, for example, introducing rigid groups such as fluorenyl epoxy resin, biphenyl or naphthalene and the like, the regularity of the resin is improved, and the crosslinking density of the matrix is improved by adopting a dual-network crosslinking system, so that the humidity resistance and the heat resistance of the matrix are improved. However, the epoxy resin treated by the above scheme still has a large amount of hydroxyl groups, and the problem that the epoxy resin is not resistant to humidity and heat is still not solved well.
Disclosure of Invention
The invention aims to provide a moisture-heat resistant epoxy resin, a preparation method and application thereof, wherein the epoxy resin has extremely high crosslinking density after being cured, and the problem that the existing epoxy resin absorbs water and is not moisture-heat resistant is solved.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides a damp-heat resistant epoxy resin which has a structure shown in a formula I:
preferably, the epoxy equivalent of the heat and humidity resistant epoxy resin is 480 to 550 g/mol.
The invention provides a preparation method of the humidity-heat resistant epoxy resin, which comprises the following steps:
mixing phenol, formaldehyde, an alkali reagent and a first solvent, and reacting to obtain an intermediate;
mixing the intermediate, epoxy chloropropane, a phase transfer catalyst, an alkali liquor and a second solvent, and carrying out condensation reaction to obtain the moisture-heat resistant epoxy resin;
the intermediate has a structure shown in a formula II;
preferably, the formaldehyde is a formaldehyde solution with the mass concentration of 37%; the alkali reagent comprises ammonia water, and the mass concentration of the ammonia water is 30%; the mass ratio of the phenol, the alkali reagent, the formaldehyde and the first solvent is 282 (50-80): 180-300): 100.
Preferably, the process of mixing phenol, formaldehyde, alkali reagent and the first solvent for reaction comprises: mixing phenol, an alkali reagent, a first solvent and a first part of formaldehyde, and carrying out condensation reaction to obtain a first product; adding a second part of formaldehyde into the first product, and sequentially carrying out a first ring-closing reaction and a first ring-opening reaction to obtain a second product; and adding a third part of formaldehyde into the second product, and sequentially carrying out a second ring-closing reaction and a second ring-opening reaction to obtain a third product and obtain an intermediate.
Preferably, the mass ratio of the first part of formaldehyde to the phenol is (60-100): 282; the mass ratio of the second part of formaldehyde to the phenol is (60-100): 282; the mass ratio of the third part of formaldehyde to the phenol is (60-100): 282.
Preferably, when the intermediate is prepared, the reaction temperature is 50-80 ℃, and the total reaction time is 60-120 min.
Preferably, the phase transfer catalyst comprises a quaternary ammonium salt catalyst, an organophosphine catalyst or an organotin catalyst.
Preferably, the alkali liquor comprises an aqueous solution of sodium hydroxide, and the mass concentration of the aqueous solution of sodium hydroxide is 30%; the mass ratio of the intermediate, the epoxy chloropropane, the phase transfer catalyst and the alkali liquor is 100 (80-100) (0.5-3) (120-150); the condensation reaction is carried out at the temperature of 90-110 ℃ for 30-90 min.
The invention provides application of the humidity-heat-resistant epoxy resin in the technical scheme or the humidity-heat-resistant epoxy resin prepared by the preparation method in the technical scheme in the field of microelectronic packaging.
The invention provides a damp-heat resistant epoxy resin which has a structure shown in a formula I:
the epoxy resin provided by the invention has a 3-functional group structure, the whole molecular chain does not contain polar groups such as hydroxyl groups and the like, the adsorption effect of the epoxy resin on water is weakened from the angle of the structure of the epoxy resin, the reduction of the physical and chemical properties of a resin cured product caused by poor moisture resistance is prevented, after the epoxy resin is mixed and cured with 4, 4' -diaminodiphenyl sulfone (DDS), the saturated water absorption rate is obviously reduced, and the problem that the polar groups in the epoxy resin easily absorb water is solved.
The molecular structure of the epoxy resin provided by the invention has a 3-functional group structure, the sites of the functional groups which are subjected to chemical crosslinking are more, the crosslinking density is far higher than that of the bisphenol A epoxy resin with 2-functional groups, the higher crosslinking density enables the gaps of the cured epoxy resin to be reduced, and the generation of microscopic cavities is reduced, so that the resin system is endowed with better heat resistance and toughness, the cured system is connected more tightly, the motion space of chain segments is small in a high-temperature state, water molecules cannot invade the interior of the resin, and the moisture absorption of the resin is further reduced. Therefore, the epoxy resin condensate formed by the epoxy resin provided by the invention has the characteristics of high crosslinking density, low water absorption and excellent processing performance, has remarkable humidity resistance and heat resistance, and is particularly suitable for the field of microelectronic packaging.
The invention provides a preparation method of the humidity-heat resistant epoxy resin, which is synthesized by using common raw materials such as phenol, formaldehyde, epoxy chloropropane and the like, and has the advantages of low cost and simple synthesis process.
Detailed Description
The invention provides a damp-heat resistant epoxy resin which has a structure shown in a formula I:
in the invention, the epoxy equivalent of the moisture-heat resistant epoxy resin is 480-550 g/mol.
The invention provides a preparation method of the humidity-heat resistant epoxy resin, which comprises the following steps:
mixing phenol, formaldehyde, an alkali reagent and a first solvent, and reacting to obtain an intermediate;
mixing the intermediate, epoxy chloropropane, a phase transfer catalyst, an alkali liquor and a second solvent, and carrying out condensation reaction to obtain the moisture-heat resistant epoxy resin;
the intermediate has a structure shown in a formula II;
in the present invention, unless otherwise specified, all the starting materials required for the preparation are commercially available products well known to those skilled in the art.
The invention mixes phenol, formaldehyde, alkali reagent and first solvent to react to obtain intermediate. In the present invention, the formaldehyde is preferably a formaldehyde solution having a mass concentration of 37%; the alkali reagent preferably comprises ammonia water, and the mass concentration of the ammonia water is preferably 30%.
In the present invention, the first solvent is preferably methanol, ethanol, acetone, diethyl ether or chloroform; the mass ratio of the phenol, the alkali reagent, the formaldehyde and the first solvent is preferably 282 (50-80): 180-300): 100, and more preferably 282 (60-65): 225-255): 100.
In the present invention, the formaldehyde is preferably added in three times, and the process of mixing the phenol, formaldehyde, alkali agent and first solvent for reaction preferably comprises: mixing phenol, an alkali reagent, a first solvent and a first part of formaldehyde, and carrying out condensation reaction to obtain a first product; adding a second part of formaldehyde into the first product, and sequentially carrying out a first ring-closing reaction and a first ring-opening reaction to obtain a second product; and adding a third part of formaldehyde into the second product, and sequentially carrying out a second ring-closing reaction and a second ring-opening reaction to obtain a third product and obtain an intermediate.
In the invention, the mass ratio of the first part of formaldehyde to the phenol is preferably (60-100): 282, more preferably (75-85): 282; the mass ratio of the second part of formaldehyde to the phenol is preferably (60-100): 282, more preferably (75-85): 282; the mass ratio of the third portion of formaldehyde to the phenol is preferably (60-100): 282, and more preferably (75-85): 282.
The process of mixing the phenol, the alkaline agent, the first solvent and the first portion of formaldehyde is not particularly limited in the present invention and may be performed according to a process well known in the art. In the invention, the condensation reaction, the first ring-closing reaction, the first ring-opening reaction, the second ring-closing reaction and the second ring-opening reaction are preferably carried out under the conditions of nitrogen atmosphere and stirring reflux; the rotating speed of the stirring is preferably 400-800 r/min, and more preferably 500 r/min.
In the invention, when the intermediate is prepared, the condensation reaction temperature is preferably 50-80 ℃, and more preferably 70 ℃; the reaction time is preferably 20 to 40min, and more preferably 30 min. The rate of heating to the condensation reaction temperature is not particularly limited in the present invention, and heating may be carried out according to a process well known in the art.
In the invention, the temperature of the first ring-closing reaction and the first ring-opening reaction is independently preferably 50-80 ℃, and more preferably 60-70 ℃; the total time of the first ring-closing reaction and the first ring-opening reaction is preferably 20-40 min, and more preferably 30 min. The invention has no special limitation on the reaction time of the first ring-closing reaction and the first ring-opening reaction, and the reaction can be fully carried out.
In the invention, the temperature of the second ring-closing reaction and the second ring-opening reaction is independently preferably 50-80 ℃, and more preferably 60-70 ℃; the total time of the second ring-closing reaction and the second ring-opening reaction is preferably 20-40 min, and more preferably 30 min. The invention has no special limitation on the reaction time of the second ring-closing reaction and the second ring-opening reaction, and the reaction is ensured to be fully carried out.
After the reaction is completed, the invention preferably makes the obtained product system stand for layering, and after cooling to room temperature, removes the liquid layer to obtain an intermediate. The process of standing for delamination, cooling and removing the liquid layer is not particularly limited in the present invention and may be performed according to a process well known in the art.
In the present invention, the process for preparing the intermediate comprises: carrying out condensation reaction on phenol and first part of formaldehyde in an alkali reagent environment to obtain a first product; carrying out a first ring-closing reaction on the second part of formaldehyde and the first product, and simultaneously carrying out a ring-opening reaction on the excessive phenol in the system and the first ring-closing reaction product to obtain a second product; carrying out a second ring-closing reaction on the third part of formaldehyde and a second product, and opening the ring of the residual phenol in the system and the second ring-closing reaction product again to obtain an intermediate, wherein the specific reaction formula is as follows:
in the invention, the total reaction time for preparing the intermediate is preferably 60-120 min, and more preferably 100 min.
After the intermediate is obtained, the intermediate, epoxy chloropropane, a phase transfer catalyst, alkali liquor and a second solvent are mixed for condensation reaction to obtain the moisture-heat resistant epoxy resin.
In the present invention, the phase transfer catalyst preferably includes a quaternary ammonium salt-based catalyst, an organophosphine-based catalyst or an organotin catalyst; the quaternary ammonium salt catalyst preferably comprises tetrabutylammonium bromide, benzyltrimethylammonium chloride or ethyltriphenylammonium bromide; the organophosphine catalyst preferably comprises triphenylmethyl phosphonium bromide or triphenylphosphine; the organotin-based catalyst preferably includes dibutyltin dilaurate.
In the present invention, the alkali solution preferably comprises an aqueous sodium hydroxide solution, and the mass concentration of the aqueous sodium hydroxide solution is preferably 30%; the second solvent preferably includes one or two of toluene, xylene, n-hexane, n-butanol, and methyl isobutyl ketone.
In the invention, the mass ratio of the intermediate, the epoxy chloropropane, the phase transfer catalyst and the alkali liquor is preferably 100 (80-100) (0.5-3) (120-150), and more preferably 100 (80-95) (1-1.5) (125-131); the mass ratio of the second solvent to the intermediate is preferably 2: 1.
In the invention, the intermediate, the epichlorohydrin, the phase transfer catalyst, the alkali liquor and the second solvent are preferably mixed in the process that the intermediate is dissolved in the second solvent, the temperature is raised to 40-60 ℃ while stirring, the epichlorohydrin is added after the intermediate is completely dissolved, the phase transfer catalyst is added after the intermediate is uniformly stirred and mixed, and the alkali liquor is dropwise added; the rotating speed of the stirring is preferably 400-800 r/min. The rate of temperature rise is not particularly limited in the present invention, and may be performed according to a procedure well known in the art.
After the process of mixing the intermediate, the epichlorohydrin, the phase transfer catalyst, the alkali liquor and the second solvent is completed, the temperature is preferably raised to the condensation reaction temperature; the heating mode is preferably linear heating, and the heating rate of the linear heating is preferably 3-6 ℃/5min, and more preferably 4 ℃/5 min.
In the invention, the condensation reaction temperature is preferably 90-110 ℃, and more preferably 95-110 ℃; the time is preferably 30-90 min.
In the present invention, the reaction formula of the condensation reaction is:
after the condensation reaction is completed, hot water is preferably added into the obtained product system, the mixture is stirred for 10-20 min, then is kept stand for layering, a water layer is removed, water washing is continued for 2-3 times, and after cooling, the solvent is removed through reduced pressure distillation, so that the humidity-heat resistant epoxy resin is obtained. The temperature and the dosage of the hot water are not specially limited, and the temperature and the dosage can be adjusted according to actual requirements. The process of stirring, standing, washing with water, cooling and distillation under reduced pressure is not particularly limited in the present invention, and may be carried out according to a process well known in the art.
The invention provides application of the humidity-heat-resistant epoxy resin in the technical scheme or the humidity-heat-resistant epoxy resin prepared by the preparation method in the technical scheme in the field of microelectronic packaging. The method of the present invention is not particularly limited, and the method may be applied according to a method known in the art.
The technical solution of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Adding 282g of phenol into a 1000mL three-neck flask, introducing nitrogen, discharging air, continuously adding 60g of ammonia water with the mass concentration of 30%, 81g of formaldehyde solution with the mass concentration of 37% and 100g of ethanol, connecting to a condenser, stirring and heating to 70 ℃, rotating at 500r/min, reacting for 30 minutes, secondly adding 81g of formaldehyde solution with the mass concentration of 37%, continuously refluxing and stirring, reacting for 30 minutes again, thirdly adding 81g of formaldehyde solution with the mass concentration of 37%, controlling the system temperature at 80 ℃ by using the volatilization and reflux of ethanol during the reaction, continuously stirring, reacting for 40 minutes, standing and layering, cooling to room temperature, removing a liquid layer, and obtaining an intermediate;
adding 100g of intermediate into a 1000mL three-neck flask again, dissolving the intermediate in 200g of dimethylbenzene, heating to 50 ℃ while stirring, adding 95g of epoxy chloropropane at one time after the intermediate is completely dissolved, stirring and mixing uniformly, adding 1.5g of phase transfer catalyst triphenylphosphine, dropwise adding 131g of sodium hydroxide aqueous solution with the mass concentration of 30%, starting linear heating after the reaction is finished, controlling the heating rate at 4 ℃/5min, heating to 95 ℃, keeping the temperature for reacting for 90min continuously, and finishing the reaction at the rotation speed of 600 r/min; adding 200g of hot water into the flask system, stirring for 20min, standing for layering, removing the water layer, continuously washing for 3 times, cooling, and distilling under reduced pressure to remove the solvent to obtain the wet-heat-resistant epoxy resin.
The epoxy equivalent of the prepared wet heat resistant epoxy resin is 507g/mol through testing.
Example 2
Phenol excess
Adding 282g of phenol into a 1000mL three-neck flask, introducing nitrogen, discharging air, continuously adding 65g of ammonia water with the mass concentration of 30%, 75g of formaldehyde solution with the mass concentration of 37% and 100g of ethanol, connecting a condenser, stirring and heating to 70 ℃, rotating at 500r/min, reacting for 30 minutes, secondly adding 75g of formaldehyde solution with the mass concentration of 37%, continuously refluxing and stirring, reacting for 30 minutes again, thirdly adding 75g of formaldehyde solution with the mass concentration of 37%, controlling the system temperature to be about 80 ℃ by utilizing the volatilization and reflux of the ethanol solution, continuously stirring, reacting for 40 minutes, standing and layering, cooling to room temperature, removing a liquid layer, and obtaining an intermediate;
adding 100g of intermediate into a 1000mL three-neck flask again, dissolving the intermediate in 200g of dimethylbenzene, heating to 50 ℃ while stirring, adding 95g of epoxy chloropropane at one time after the intermediate is completely dissolved, stirring and mixing uniformly, adding 1g of phase transfer catalyst benzyltrimethylammonium chloride, dropwise adding 125g of sodium hydroxide aqueous solution with the mass concentration of 30%, starting linear heating after the reaction is finished, controlling the heating rate at 4 ℃/5min, heating to 95 ℃, keeping the temperature for reacting for 90min continuously, and finishing the reaction at the rotation speed of 600 r/min; adding 200g of hot water into the flask system, stirring for 20min, standing for layering, removing the water layer, continuously washing with water for 3 times, cooling, and distilling under reduced pressure to remove the solvent to obtain the humidity-heat resistant epoxy resin.
The epoxy equivalent of the prepared wet heat resistant epoxy resin is 542g/mol through testing.
Example 3
Excess of formaldehyde
Adding 282g of phenol into a 1000mL three-neck flask, introducing nitrogen, discharging air, continuously adding 65g of ammonia water with the mass concentration of 30%, 85g of formaldehyde solution with the mass concentration of 37% and 100g of ethanol, connecting a condenser, stirring and heating to 70 ℃, rotating at 500r/min, reacting for 30 minutes, secondly adding 85g of formaldehyde solution with the mass concentration of 37%, continuously refluxing and stirring, reacting for 30 minutes again, thirdly adding 85g of formaldehyde solution with the mass concentration of 37%, controlling the system temperature to be about 80 ℃ by utilizing the volatilization and reflux of the ethanol solution, continuously stirring, reacting for 40 minutes, standing and layering, cooling to room temperature, removing a liquid layer, and obtaining an intermediate;
adding 100g of intermediate into a 1000mL three-neck flask again, dissolving the intermediate in 200g of dimethylbenzene, heating to 50 ℃ while stirring, adding 95g of epoxy chloropropane at one time after the intermediate is completely dissolved, stirring and mixing uniformly, adding 1.5g of dibutyltin dilaurate serving as a phase transfer catalyst, dropwise adding 131g of sodium hydroxide aqueous solution with the mass concentration of 30%, starting linear heating after the reaction is finished, controlling the heating rate to be 4 ℃/5min, heating to 95 ℃, continuing to react for 90min at constant temperature and the rotating speed of 600r/min, adding 200g of hot water into the flask system after the reaction is finished, stirring for 15min, standing for layering, removing the water layer, continuing to wash for 3 times, cooling, and distilling under reduced pressure to remove the solvent to obtain the moisture-heat-resistant epoxy resin.
The epoxy equivalent of the prepared wet heat resistant epoxy resin is 615g/mol through testing.
Comparative example 1
A commercially available bisphenol A epoxy resin E-20 epoxy resin was used as comparative example 1 (purchased from New Material science and technology Co., Ltd., Anhui).
Performance testing
1) After the epoxy resins prepared in examples 1 to 3 and the epoxy resin of comparative example 1 were mixed uniformly with the calculated amount of DDS, a standard sample of 40mm x 8mm x 2.5mm was prepared, and after curing at 180 ℃ x 2h +200 ℃ x 3h, the high temperature moisture resistance and the glass transition temperature drop were measured, wherein:
moisture and heat resistance test: placing the sample in hot water at 98 ℃ for soaking for 24h, and testing the saturated water absorption; change in glass transition temperature: testing the glass transition temperature of the cured product formed after curing before boiling and after boiling by DSC; the results are shown in Table 1.
TABLE 1 Performance data for epoxy resins of examples 1-3 and comparative example 1
As shown in Table 1, the moisture and heat resistant epoxy resin provided by the invention has the advantages that the saturated water absorption rate is reduced to be less than 50% of that of the commercial bisphenol A epoxy resin, and the water absorption rate is low; the glass transition temperature reduction amplitude of the epoxy resin after being boiled in water is obviously reduced, which shows that the water-resistant effect is obvious; in addition, a cured product formed by the epoxy resin provided by the invention still has a higher glass transition temperature after being boiled in water, which shows that the heat resistance is obviously improved.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (10)
2. the wet heat resistant epoxy resin as claimed in claim 1, wherein the epoxy equivalent of the wet heat resistant epoxy resin is 480 to 550 g/mol.
3. The method for preparing the wet heat resistant epoxy resin of claim 1 or 2, comprising the steps of:
mixing phenol, formaldehyde, an alkali reagent and a first solvent, and reacting to obtain an intermediate;
mixing the intermediate, epoxy chloropropane, a phase transfer catalyst, an alkali liquor and a second solvent, and carrying out condensation reaction to obtain the moisture-heat resistant epoxy resin;
the intermediate has a structure shown in a formula II;
4. the production method according to claim 3, characterized in that the formaldehyde is a formaldehyde solution having a mass concentration of 37%; the alkali reagent comprises ammonia water, and the mass concentration of the ammonia water is 30%; the mass ratio of the phenol, the alkali reagent, the formaldehyde and the first solvent is 282 (50-80): 180-300): 100.
5. The preparation method according to claim 3 or 4, wherein the mixing of the phenol, the formaldehyde, the alkali reagent and the first solvent for reaction comprises: mixing phenol, an alkali reagent, a first solvent and a first part of formaldehyde, and carrying out condensation reaction to obtain a first product; adding a second part of formaldehyde into the first product, and sequentially carrying out a first ring-closing reaction and a first ring-opening reaction to obtain a second product; and adding a third part of formaldehyde into the second product, and sequentially carrying out a second ring-closing reaction and a second ring-opening reaction to obtain a third product and obtain an intermediate.
6. The method according to claim 5, wherein the mass ratio of the first portion of formaldehyde to phenol is (60-100): 282; the mass ratio of the second part of formaldehyde to the phenol is (60-100): 282; the mass ratio of the third part of formaldehyde to the phenol is (60-100): 282.
7. The method according to claim 3, wherein the intermediate is prepared at a reaction temperature of 50 to 80 ℃ for a total reaction time of 60 to 120 min.
8. The production method according to claim 3, wherein the phase transfer catalyst comprises a quaternary ammonium salt-based catalyst, an organophosphine-based catalyst, or an organotin catalyst.
9. The preparation method according to claim 3, characterized in that the alkali solution comprises an aqueous sodium hydroxide solution, the mass concentration of the aqueous sodium hydroxide solution is 30%; the mass ratio of the intermediate, the epoxy chloropropane, the phase transfer catalyst and the alkali liquor is 100 (80-100) (0.5-3) (120-150); the condensation reaction is carried out at the temperature of 90-110 ℃ for 30-90 min.
10. The application of the humidity-heat-resistant epoxy resin as described in claim 1 or 2 or the humidity-heat-resistant epoxy resin prepared by the preparation method as described in any one of claims 3 to 9 in the field of microelectronic packaging.
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