CN103725003B - A kind of modified bismaleimide resin composition and method of making the same with high wet-hot aging performance - Google Patents
A kind of modified bismaleimide resin composition and method of making the same with high wet-hot aging performance Download PDFInfo
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Abstract
The invention discloses a kind of modified bismaleimide resin composition and method of making the same with high wet-hot aging performance.Described modified bismaleimide resin composition by weight, comprises following component: bimaleimide resin 100 parts, allylic cpd 50 ~ 100 parts, phenol modification xylene formaldehyde resin 15 ~ 50 parts, 0.5 ~ 5 part, solidifying agent.Its preparation method is: bimaleimide resin and the allylic cpd of getting formula ratio are placed in reactor, are warming up to 120 ~ 145 DEG C, is incubated to resin melting follow-up continuation of insurance temperature stirring reaction 10 ~ 30min; Add the mixing of phenol modification xylene formaldehyde resin; Be cooled to 90 ~ 100 DEG C again and add solidifying agent, through vacuum defoaming treatment after mixing, to obtain final product.Resin combination of the present invention, after solidification, also can improve the moistureproofness of appliance electronic component, chemical proofing and reliability while keeping the excellent properties of bimaleimide resin own.
Description
Technical field
The present invention relates to a kind of resin combination, be specifically related to a kind of modified bismaleimide resin composition and method of making the same with high wet-hot aging performance.
Background technology
Bismaleimides (BMI) resin is as the main base resin of advanced composite material, there is good resistance toheat and mechanical property, but its main deficiency of unmodified BMI resin is that the fragility of its cured article is large, have to pass through toughening modifying and just there is practical value, the molecular configuration of BMI resin is firm, although thermotolerance is high, but processing characteristics is not good enough, in order to overcome these deficiencies above-mentioned, researchist has carried out a lot of study on the modification to BMI resin, the most frequently used method of modifying carries out modification by copolymerization with epoxy resin etc., and achieve good progress and effect.Along with the raising of the application requiring of the high-end technical fields such as electric appliance and electronic, more requirement is proposed to bimaleimide resin, but add diallyl compound, reduction that diamine, epoxy resin can cause thermotolerance or humidity resistance, therefore the over-all properties of existing bimaleimide resin composition needs to be improved further.Those skilled in the art will know that, bimaleimide resin is obtained through polycondensation cyclodehydration by two maleinamic acid, thus in molecular configuration, the group of bimaleimide resin still has very strong wetting ability, moisture resistivity is poor, after making moist or soaking, insulating property can sharply decline, and water molecules can permeate along intermolecular hole to material internal, and under damp and hot or moist environment, its reliability can obviously reduce.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of modified bismaleimide resin composition and method of making the same with high wet-hot aging performance.Modified bismaleimide resin composition obtained by this method has higher impelling strength, better humidity resistance and higher second-order transition temperature after solidification.
The modified bismaleimide resin composition with high wet-hot aging performance of the present invention, by weight, comprises following component:
Bimaleimide resin 100 parts, allylic cpd 50 ~ 100 parts, phenol modification xylene formaldehyde resin 15 ~ 50 parts, 0.5 ~ 5 part, solidifying agent.
The present invention effectively improves the anti-moisture performance of bimaleimide resin by adding phenol modification xylene formaldehyde resin.In the resin structure of phenol modification xylene formaldehyde resin, be introduced in system containing a large amount of diformazan phenyl ring and finally can be present in gained modified bismaleimide resin composition to increase its hydrophobic property, in addition also containing hydroxyl, methoxyl group and the ehter bond that can react, be introduced in system and the cross-linking density of gained modified bismaleimide resin composition can be made to decrease, toughness can increase to some extent, thus makes gained modified bismaleimide resin composition have higher physical strength and shelf stability; In addition, phenol modification xylene formaldehyde resin has a certain proportion of phenol ring structure, and the last crosslinking curing of modified resin thus can be made to become reticulated structure; Therefore, by adding phenol modification xylene formaldehyde resin, modification is carried out to bimaleimide resin, while the thermotolerance keeping bimaleimide resin and toughness reguirements, effectively improve humidity resistance and the wet-hot aging performance of gained modified bismaleimide resin composition.
In above-mentioned modified bismaleimide resin composition, the weight part of each component is preferably:
Bimaleimide resin 100 parts, allylic cpd 60 ~ 80 parts, phenol modification xylene formaldehyde resin 15 ~ 35 parts, 0.5 ~ 3 part, solidifying agent.
In technique scheme,
Described bimaleimide resin can be specifically be selected from one or more the combination in 4,4'-diphenyl methane dimaleimide, 4,4'-Diphenyl Ether Bismaleimides and 4,4'-sulfobenzide bismaleimides.When bimaleimide resin be chosen as above-mentioned two or more combination time, the proportioning between them can be any proportioning.
Described allylic cpd can be specifically be selected from one or more the combination in diallyl bisphenol (DABPA), diallyl bisphenol S, allyl group cresols (AC) and chavicol, chavicol wherein can be o-allyl phenol or p-allylphenol, also can be the mixing of arbitrary proportion both them.When diallyl compound be chosen as above-mentioned two or more combination time, the proportioning between them can be any proportioning.
Described phenol modification xylene formaldehyde resin is (also referred to as phenol modification xylene resin, or be called xylene resin or xylene resin oligopolymer), for phenol and xylene resin react in the presence of acid catalyst and obtain, its molecular weight is generally 300 ~ 500Da, fusing point 70 ~ 100 DEG C.Specifically can adopt the phenol modification xylene formaldehyde resin that the company such as Suzhou Speical Chemical Co., Ltd., Shanghai Jin Yue Chemical Co., Ltd. produces.
Described solidifying agent is same as the prior art, can be specifically hexamethylenetetramine.
The above-mentioned preparation method with the modified bismaleimide resin composition of high wet-hot aging performance, be specially: get the bimaleimide resin of 100 weight parts and the allylic cpd of 50 ~ 100 parts is placed in reactor, be warming up to 120 ~ 145 DEG C, insulated and stirred, until resin melting is transparent, continues insulated and stirred reaction 10 ~ 30min; Then add the phenol modification xylene formaldehyde resin of 10 ~ 50 weight parts, mix; Be cooled to the solidifying agent that 90 ~ 100 DEG C add 0.5 ~ 5 weight part afterwards, mix; Again through vacuum defoaming treatment, namely obtain the modified bismaleimide resin composition with high wet-hot aging performance.
In above-mentioned preparation method, the diallyl compound of the bimaleimide resin of 100 weight parts and 50 ~ 100 parts is being placed in reactor, after being warming up to 120 ~ 145 DEG C, insulated and stirred until resin melting transparent time approximately need 10 ~ 30min.
In above-mentioned preparation method, after adding phenol modification xylene formaldehyde resin normally insulated and stirred 20 ~ 30min to reach the object mixed.
In above-mentioned preparation method, after adding solidifying agent normally insulated and stirred 8 ~ 15min to reach the object mixed.
In above-mentioned preparation method, can will obtain the bimaleimide resin cured article of modification after the modified bismaleimide resin composition of gained routinely solidification treatment, concrete curing process is generally: 120 DEG C/1h+150 DEG C/2h+180 DEG C/2h+210 DEG C/5h.
In above-mentioned preparation method, described bimaleimide resin can be specifically be selected from one or more the combination in 4,4'-diphenyl methane dimaleimide, 4,4'-Diphenyl Ether Bismaleimides and 4,4'-sulfobenzide bismaleimides; When bimaleimide resin be chosen as above-mentioned two or more combination time, the proportioning between them can be any proportioning.Described diallyl compound can be specifically be selected from one or more the combination in diallyl bisphenol, diallyl bisphenol S, allyl group cresols and chavicol, chavicol wherein can be o-allyl phenol or p-allylphenol, also can be the mixing of arbitrary proportion both them; When diallyl compound be chosen as above-mentioned two or more combination time, the proportioning between them can be any proportioning.Described phenol modification xylene formaldehyde resin is (also referred to as phenol modification xylene resin, or be called xylene resin phenol modification xylene formaldehyde resin), for phenol and xylene resin react in the presence of acid catalyst and obtain, its molecular weight is generally 300 ~ 500Da, fusing point 70 ~ 100 DEG C.Specifically can adopt the phenol modification xylene formaldehyde resin that the company such as Suzhou Speical Chemical Co., Ltd., Shanghai Jin Yue Chemical Co., Ltd. produces.Described solidifying agent is same as the prior art, can be specifically hexamethylenetetramine.
Applicant finds through lot of experiments, the modified bismaleimide resin composition obtained by the method for the invention is after solidification, there are excellent electromechanical properties, not only maintain the excellent properties (feature as thermotolerance) of bimaleimide resin itself, also can improve the moistureproofness of appliance electronic component, chemical proofing and unfailing performance.
Compared with prior art, feature of the present invention is:
1, the present invention is by specific proportions blended to reach the object improving the performances such as resin structure, water-intake rate and humidity resistance of the bismaleimides adopting high heat resistance and phenol modification xylene formaldehyde resin two kinds of thermosetting resins with benzene ring structure, the blending resin casting matrix of gained is had after solidification and than the bismaleimides cured article of homopolymerization, there is higher impelling strength, better humidity resistance and higher second-order transition temperature, improve equipment reliability of operation in a humidity environment;
2, the resin system of gained has good manufacturability, prepares high temperature resistant, high performance matrix material by the technique such as mold pressing, cast.
Embodiment
Below by specific embodiment, the invention will be further described, but the present invention is not limited to these embodiments.
Number described in following embodiment is weight part.
Chavicol involved in following embodiment is all purchased from Honghu Shuangma New Materials Technology Co., Ltd., and described phenol modification xylene formaldehyde resin is all purchased from Suzhou Speical Chemical Co., Ltd..
Embodiment 1
By 100 parts 4,4'-diphenyl methane dimaleimide, the diallyl bisphenol of 60 parts is placed in reactor, be warming up to 140 DEG C, insulated and stirred is until resin melting transparent (now 4,4'-diphenyl methane dimaleimide and diallyl bisphenol are melting vitreous state), continue insulated and stirred reaction 20min; Then under insulated and stirred condition, the phenol modification xylene formaldehyde resin of 10 parts is added, insulated and stirred 20min; Be cooled to the hexamethylenetetramine that 95 DEG C add 0.5 part afterwards, stir 10min at such a temperature; Finally obtain modified bismaleimide resin composition through vacuum defoaming treatment again.
After the technique solidification of the modified bismaleimide resin composition of the present embodiment gained by 120 DEG C/1h+150 DEG C/2h+180 DEG C/2h+210 DEG C/5h, obtain the bimaleimide resin cured article of modification.Test the electromechanical properties of the bimaleimide resin cured article of the modification of gained, result is as shown in table 1.
Comparative example 1
By 100 parts 4,4'-diphenyl methane dimaleimide, 60 parts of diallyl bisphenols, be placed in reactor, be warming up to 140 DEG C, insulated and stirred, until resin melting transparent (now 4,4'-diphenyl methane dimaleimides and diallyl bisphenol are melting vitreous state), continues insulated and stirred reaction 20min; Then under insulated and stirred condition, add the epoxy resin CYD-128 insulated and stirred 20min of 30 parts; The epoxy hardener methyl hexahydrophthalic anhydride of 20 parts is added, 10min under this temperature stirs when being cooled to 95 DEG C afterwards; The last bimaleimide resin composition obtaining modification again after vacuum froth breaking.
After the technique solidification of the modified bismaleimide resin of this comparative example gained by 120 DEG C/1h+150 DEG C/2h+180 DEG C/2h+210 DEG C/5h, obtain the bimaleimide resin cured article of modification.Test the electromechanical properties of the bimaleimide resin cured article of the modification of gained, result is as shown in table 1.
Embodiment 2
By 100 parts 4,4'-diphenyl methane dimaleimide, the diallyl bisphenol of 80 parts is placed in reactor, be warming up to 130 DEG C, insulated and stirred is until resin melting transparent (now 4,4'-diphenyl methane dimaleimide and diallyl bisphenol are melting vitreous state), continue insulated and stirred reaction 30min; Then under insulated and stirred condition, the phenol modification xylene formaldehyde resin of 20 parts is added, insulated and stirred 30min; Be cooled to the hexamethylenetetramine that 100 DEG C add 1 part afterwards, stir 8min at such a temperature; Finally obtain modified bismaleimide resin composition through vacuum defoaming treatment again.
After the technique solidification of the modified bismaleimide resin composition of the present embodiment gained by 120 DEG C/1h+150 DEG C/2h+180 DEG C/2h+210 DEG C/5h, obtain the bimaleimide resin cured article of modification.Test the electromechanical properties of the bimaleimide resin cured article of the modification of gained, result is as shown in table 1.
Embodiment 3
By 100 parts 4,4'-diphenyl methane dimaleimide, the diallyl bisphenol of 55 parts and the allyl group cresols of 25 parts are placed in reactor, be warming up to 130 DEG C, insulated and stirred is until resin melting transparent (now 4,4'-diphenyl methane dimaleimide, diallyl bisphenol and allyl group cresols are melting vitreous state), continue insulated and stirred reaction 30min; Then under insulated and stirred condition, the phenol modification xylene formaldehyde resin of 10 parts is added, insulated and stirred 20min; Be cooled to the hexamethylenetetramine that 90 DEG C add 0.5 part afterwards, stir 10min at such a temperature; Finally obtain modified bismaleimide resin composition through vacuum defoaming treatment again.
After the technique solidification of the modified bismaleimide resin composition of the present embodiment gained by 120 DEG C/1h+150 DEG C/2h+180 DEG C/2h+210 DEG C/5h, obtain the bimaleimide resin cured article of modification.Test the electromechanical properties of the bimaleimide resin cured article of the modification of gained, result is as shown in table 1.
Embodiment 4
By 100 parts 4,4'-sulfobenzide bismaleimides, the diallyl bisphenol of 55 parts and 25 parts of allyl group cresols are placed in reactor, be warming up to 130 DEG C, insulated and stirred is until resin melting transparent (now 4,4'-sulfobenzide bismaleimides, diallyl bisphenol and allyl group cresols are melting vitreous state), continue insulated and stirred reaction 30min; Then under insulated and stirred condition, the phenol modification xylene formaldehyde resin of 30 parts is added, insulated and stirred 20min; Be cooled to the hexamethylenetetramine that 90 DEG C add 1.5 parts afterwards, 8min under this temperature stirs; Finally obtain modified bismaleimide resin composition through vacuum defoaming treatment again.
After the technique solidification of the modified bismaleimide resin composition of the present embodiment gained by 120 DEG C/1h+150 DEG C/2h+180 DEG C/2h+210 DEG C/5h, obtain the bimaleimide resin cured article of modification.Test the electromechanical properties of the bimaleimide resin cured article of the modification of gained, result is as shown in table 1.
Embodiment 5
By 50 parts 4,4'-diphenyl methane dimaleimide, 50 parts 4,4'-sulfobenzide bismaleimides, the diallyl bisphenol of 30 parts and 40 parts of allyl group cresols are placed in reactor, be warming up to 130 DEG C, insulated and stirred is until resin melting transparent (now 4,4'-diphenyl methane dimaleimide, 4,4'-sulfobenzide bismaleimidess, diallyl bisphenol and allyl group cresols are melting vitreous state), continue insulated and stirred reaction 25min; Then under insulated and stirred condition, the phenol modification xylene formaldehyde resin of 30 parts is added, insulated and stirred 20min; Be cooled to the hexamethylenetetramine that 90 DEG C add 1.5 parts afterwards, 10min under this temperature stirs; Finally obtain modified bismaleimide resin composition through vacuum defoaming treatment again.
After the technique solidification of the modified bismaleimide resin composition of the present embodiment gained by 120 DEG C/1h+150 DEG C/2h+180 DEG C/2h+210 DEG C/5h, obtain the bimaleimide resin cured article of modification.Test the electromechanical properties of the bimaleimide resin cured article of the modification of gained, result is as shown in table 1.
Embodiment 6
By 60 parts 4,4'-diphenyl methane dimaleimide, 40 parts 4,4'-Diphenyl Ether Bismaleimide, the diallyl bisphenol of 55 parts and 25 parts of allyl group cresols are placed in reactor, be warming up to 145 DEG C, insulated and stirred is until resin melting transparent (now 4,4'-diphenyl methane dimaleimide, 4,4'-Diphenyl Ether Bismaleimides, diallyl bisphenol and allyl group cresols are melting vitreous state), continue insulated and stirred reaction 20min; Then under insulated and stirred condition, the phenol modification xylene formaldehyde resin of 35 parts is added, insulated and stirred 25min; Be cooled to the hexamethylenetetramine that 90 DEG C add 1.5 parts afterwards, 12min under this temperature stirs; Finally obtain modified bismaleimide resin composition through vacuum defoaming treatment again.
After the technique solidification of the modified bismaleimide resin composition of the present embodiment gained by 120 DEG C/1h+150 DEG C/2h+180 DEG C/2h+210 DEG C/5h, obtain the bimaleimide resin cured article of modification.Test the electromechanical properties of the bimaleimide resin cured article of the modification of gained, result is as shown in table 1.
Embodiment 7
By 100 parts 4,4'-Diphenyl Ether Bismaleimide, the diallyl bisphenol of 60 parts and 20 parts of chavicols are placed in reactor, be warming up to 130 DEG C, insulated and stirred is until resin melting transparent (now 4,4'-Diphenyl Ether Bismaleimide, diallyl bisphenol and chavicol are melting vitreous state), continue insulated and stirred reaction 30min; Then under insulated and stirred condition, the phenol modification xylene formaldehyde resin of 40 parts is added, insulated and stirred 25min; Be cooled to the hexamethylenetetramine that 90 DEG C add 1.5 parts afterwards, 10min under this temperature stirs; Finally obtain modified bismaleimide resin composition through vacuum defoaming treatment again.
After the technique solidification of the modified bismaleimide resin composition of the present embodiment gained by 120 DEG C/1h+150 DEG C/2h+180 DEG C/2h+210 DEG C/5h, obtain the bimaleimide resin cured article of modification.Test the electromechanical properties of the bimaleimide resin cured article of the modification of gained, result is as shown in table 1.
Comparative example 2 (the corresponding embodiment 7 of this comparative example)
By 100 parts 4, the chavicol of 4'-Diphenyl Ether Bismaleimide, 60 parts of diallyl bisphenols and 20 parts is placed in reactor, be warming up to 130 DEG C, insulated and stirred is until resin melting transparent (now 4,4'-Diphenyl Ether Bismaleimide, diallyl bisphenol and chavicol are melting vitreous state), continue insulated and stirred reaction 30min; Then under insulated and stirred condition, add the epoxy resin CYD-128 insulated and stirred 20min of 40 parts; Add the epoxy hardener methyl hexahydrophthalic anhydride of 35 parts when being cooled to 90 DEG C afterwards, this temperature stir under 10 minutes; 10min under this temperature stirs; The last bimaleimide resin composition obtaining modification again after vacuum froth breaking.
After the technique solidification of the modified bismaleimide resin of this comparative example gained by 120 DEG C/1h+150 DEG C/2h+180 DEG C/2h+210 DEG C/5h, obtain the bimaleimide resin cured article of modification.Test the electromechanical properties of the bimaleimide resin cured article of the modification of gained, result is as shown in table 1.
Embodiment 8
By 100 parts 4,4'-Diphenyl Ether Bismaleimide, the diallyl bisphenol of 90 parts are placed in reactor, be warming up to 120 DEG C, insulated and stirred is until resin melting transparent (now 4,4'-Diphenyl Ether Bismaleimide and diallyl bisphenol are melting vitreous state), continue insulated and stirred reaction 30min; Then the phenol modification xylene formaldehyde resin adding 50 parts under insulated and stirred condition mixes, and is cooled to the hexamethylenetetramine that 95 DEG C add 1.5 parts, 15min under this temperature stirs; Finally obtain modified bismaleimide resin composition through vacuum defoaming treatment again.
After the technique solidification of the modified bismaleimide resin composition of the present embodiment gained by 120 DEG C/1h+150 DEG C/2h+180 DEG C/2h+210 DEG C/5h, obtain the bimaleimide resin cured article of modification.Test the electromechanical properties of the bimaleimide resin cured article of the modification of gained, result is as shown in table 1.
Embodiment 9
By 100 parts 4,4'-Diphenyl Ether Bismaleimide, the diallyl bisphenol S of 100 parts are placed in reactor, be warming up to 130 DEG C, insulated and stirred is until resin melting transparent (now 4,4'-Diphenyl Ether Bismaleimide and diallyl bisphenol S are melting vitreous state), continue insulated and stirred reaction 25min; Then under insulated and stirred condition, the phenol modification xylene formaldehyde resin of 15 parts is added, insulated and stirred 20min; Be cooled to the hexamethylenetetramine that 90 DEG C add 5 parts afterwards, 10min under this temperature stirs; Finally obtain modified bismaleimide resin composition through vacuum defoaming treatment again.
After the technique solidification of the modified bismaleimide resin composition of the present embodiment gained by 120 DEG C/1h+150 DEG C/2h+180 DEG C/2h+210 DEG C/5h, obtain the bimaleimide resin cured article of modification.Test the electromechanical properties of the bimaleimide resin cured article of the modification of gained, result is as shown in table 1.
Table 1:
Note: water tolerance test condition: 100 DEG C of water, 96 hours.
From data in table 1, with the bimaleimide resin composition of phenol modification xylene formaldehyde resin modification, maintain the original thermotolerance of bimaleimide resin and higher heat-drawn wire on the one hand, make bimaleimide resin have better humidity resistance on the other hand, electromechanical properties are improved.Test-results shows, along with the increase of phenol modification xylene formaldehyde resin add-on, the heat-drawn wire of the modified bismaleimide resin composition wet-hot aging performance that slightly declines then has raising by a relatively large margin.When the add-on of phenol modification xylene formaldehyde resin controls when the scope of 15 ~ 35 parts, the over-all properties of prepared modified bismaleimide resin composition is more good, can meet the requirement of appliance electronic component reliability under the severe environment such as damp and hot.
Claims (5)
1. one kind has the preparation method of the modified bismaleimide resin composition of high wet-hot aging performance, it is characterized in that: get the bimaleimide resin of 100 weight parts and the allylic cpd of 50 ~ 100 parts is placed in reactor, be warming up to 120 ~ 145 DEG C, insulated and stirred, until resin melting is transparent, continues insulated and stirred reaction 10 ~ 30min; Then add the phenol modification xylene formaldehyde resin of 10 ~ 50 weight parts, mix; Be cooled to the solidifying agent that 90 ~ 100 DEG C add 0.5 ~ 5 weight part afterwards, mix; Again through vacuum defoaming treatment, namely obtain the modified bismaleimide resin composition with high wet-hot aging performance.
2. the preparation method with the modified bismaleimide resin composition of high wet-hot aging performance according to claim 1, is characterized in that: insulated and stirred 20 ~ 30min after adding phenol modification xylene formaldehyde resin.
3. the preparation method with the modified bismaleimide resin composition of high wet-hot aging performance according to claim 1 and 2, is characterized in that: the modified bismaleimide resin composition of gained obtains the bimaleimide resin cured article of modification after conventional solidification treatment.
4. the preparation method with the modified bismaleimide resin composition of high wet-hot aging performance according to claim 1 and 2, it is characterized in that: described bimaleimide resin is for being selected from 4,4'-diphenyl methane dimaleimide, 4, one or more combination in 4'-Diphenyl Ether Bismaleimide and 4,4'-sulfobenzide bismaleimides.
5. the preparation method with the modified bismaleimide resin composition of high wet-hot aging performance according to claim 1 and 2, is characterized in that: described allylic cpd is be selected from one or more the combination in diallyl bisphenol, diallyl bisphenol S, allyl group cresols and chavicol.
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| KR20190035731A (en) * | 2016-08-05 | 2019-04-03 | 닛뽄 가야쿠 가부시키가이샤 | Maleimide resin composition, prepreg, cured product thereof, and semiconductor device |
| CN107011657B (en) * | 2017-03-28 | 2019-05-21 | 中国科学院化学研究所 | A kind of high-ductility bimaleimide resin and its preparation method and application |
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