CN102876280A - Cyanate ester/bis-oxazoline thermostable adhesive and preparation method thereof - Google Patents
Cyanate ester/bis-oxazoline thermostable adhesive and preparation method thereof Download PDFInfo
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- CN102876280A CN102876280A CN2012103168787A CN201210316878A CN102876280A CN 102876280 A CN102876280 A CN 102876280A CN 2012103168787 A CN2012103168787 A CN 2012103168787A CN 201210316878 A CN201210316878 A CN 201210316878A CN 102876280 A CN102876280 A CN 102876280A
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Abstract
The invention provides a cyanate ester/bis-oxazoline thermostable adhesive and a preparation method thereof. The preparation method comprises the following steps of: uniformly mixing 20 to 50 parts of cyanate ester resin and 10 to 40 parts of bismaleimide resin at the temperature of 120 to 200 DEG C; and pouring 1 to 20 parts of bis-oxazoline compound, 5 to 30 parts of epoxy resin and 3 to 40 parts of solvent into a three-mouth flask at the temperature of 60 to 120 DEG C, and continuously stirring to make the mixture be uniformly mixed so as to obtain the cyanate ester/bis-oxazoline thermostable adhesive. The adhesive has high thermostability and good dielectric properties and can have tremendous application prospects in the high-tech fields of high-performance adhesives, electronic packaging materials, aerospace engineering, electronics and the like. The preparation method has the characteristics of high adaptability, simple operation process and the like.
Description
Technical field
The present invention relates to a kind of cyanate/bisoxazoline high-temperature resistance adhesive and preparation method thereof, that a kind of employing contains Cyanate Resin Modified by Prepolymer of Bismaleimide as matrix, with the dilution Resins, epoxy He the bisoxazoline compound as modified filler, utilize the resistant to elevated temperatures tackiness agent of traditional thermal curing methods preparation, can be widely used in the high-tech areas such as aerospace, electric power, electronics.
Background technology
Cyanate (CE) resin is a class end group with the thermosetting resin [22] of-OCN functional group, cyanate has good thermotolerance, humidity resistance, solvability and excellent dielectric properties and becomes the high-performance polymer of very attractive, the cyanate tackiness agent has excellent dielectric properties, is applicable to the bonding of electronic industry wiring board and encapsulation; This type of tackiness agent can form chemical bond with the groups such as hydroxyl of metallic surface, thereby metal is had fabulous cementability; In solidification process, produce without small molecules, can be under low pressure and lesser temps curing molding.Compare with epoxy adhesive, the cyanate tackiness agent at high temperature uses and moisture or thermal destruction do not occur, have higher thermotolerance, better dielectric properties, minimum water absorbability and good dimensional stability, be a class excellent combination property high-temperature resistance adhesive (reference: 1, HAMERTON I.Chemistry and Technology of Cyanate Ester Resin[M], Blackie Academic and Professional, Glasgow, UK, 1994).Functional group-the OCN of cyanate ester resin has very high reactive behavior, easily with the compound such as epoxide group, amino and unsaturated double-bond or polymkeric substance generation copolyreaction (reference: 2, POKORNY R J.Cyanate resin adhesive for polyimide film:US, 5350635[P] .1994-09-27).Contain imide ring and aromatic ring rigid structure in the BMI resinous molecular structure, have excellent resistance toheat and wet-hot aging performance, C=C in the BMI monomer structure easily carries out addition reaction with the compound that contains reactive hydrogen, can carry out copolyreaction with the BMI of the compound that contains unsaturated double-bond, Resins, epoxy and other structure, can also issue in catalyzer or heat effect in addition and be conigenous poly-reaction.With the modified resin of cyanate and bismaleimides blend formation, expection is both advantages comprehensively, obtain having the high-temperature resistance adhesive of superior heat resistance.
Tackiness agent is the material that by interface interaction (chemical force, physical force) various materials is bonded together securely with a kind of, referred to as glue.The tackiness agent that physical property mass-energy satisfies service requirements when at high temperature using is called high-temperature resistance adhesive.Along with the development of science and technology, more and more higher to the stable on heating requirement of tackiness agent, the research of high temperature resistant synthetic organic adhesion agent and application are more and more extensive.Progress along with science and technology, the high-tech areas such as aerospace, electric power, electronics are more and more higher to the requirement of material thermal resistance, performance requriements to its high-temperature resistance adhesive is also further harsh, existing high-temperature resistance adhesive can not well adapt to the needs of the high-tech areas such as aerospace, electric power, electronics, so further improve the important directions that the performance of performance resins high-temperature resistance adhesive becomes current research.
Summary of the invention
The technical problem that solves
For fear of the deficiencies in the prior art part, the present invention proposes a kind of cyanate/bisoxazoline high-temperature resistance adhesive and preparation method thereof, is a kind ofly to can be used as electronic package material and have cyanate ester resin high-temperature resistance adhesive of good electricity saving performance and preparation method thereof.
Technical scheme
A kind of cyanate/bisoxazoline high-temperature resistance adhesive is characterized in that component is: 5～30 parts of 20～50 parts of cyanate ester resins, 1～20 part of 10～40 parts of, bisoxazolines of bimaleimide resin compound and Resins, epoxy also comprise 3～40 parts of solvents; Described umber is weight part.
Described cyanate ester resin is a kind of in bisphenol A cyanate ester resin, Novolac Cyanate Ester Resins, bis-phenol M type cyanate ester resin or the line style Novolac Cyanate Ester Resins, or its many persons' mixture.
Described bimaleimide resin is any in ditane type bismaleimides, a penylene bismaleimides, diphenyl ether type bismaleimides, diallyl type bismaleimides, diamino-anthraquinone bismaleimides or the oxadiazole structure to prolong type bimaleimide resin, or its many persons' mixture.
Described bisoxazoline compound is 2,2 '-(Isosorbide-5-Nitrae-phenylene)-bisoxazolines or 2,2 '-(1,3-phenylene)-bisoxazolines, or both mixtures.
Described Resins, epoxy is any in E-51 Resins, epoxy, E-44 Resins, epoxy, AG-80 Resins, epoxy, TDE-85 Resins, epoxy or the bisphenol A type epoxy resin, or its many persons' mixture.
Described solvent is any in dehydrated alcohol, dimethyl formamide, dimethylbenzene, pimelinketone, N,N-DIMETHYLACETAMIDE or the trieline, or its many persons' mixture.
A kind of method for preparing described cyanate/bisoxazoline high-temperature resistance adhesive is characterized in that step is as follows:
Step 1: 20～50 parts of cyanate ester resins and 10～40 parts of bimaleimide resins are put into there-necked flask or reactor, and melting and copolymer-1 0min～100min under 120～200 ℃ temperature obtain cyanate/bimaleimide resin performed polymer;
Step 2: the solvent of 5～30 parts Resins, epoxy and 3～40 parts is at room temperature stirred, Resins, epoxy is dissolved in the solvent fully, the Resins, epoxy after obtaining diluting;
Step 3: then the cyanate of step 1 preparation/bimaleimide resin performed polymer is reduced temperature to 60～120 ℃, the Resins, epoxy of step 2 and 1～20 part of De bisoxazoline compound join condensing reflux in cyanate/bismaleimides performed polymer, and melting copolymerization 20min～70min, obtain cyanate/bisoxazoline high-temperature resistance adhesive;
Umber in the above-mentioned steps is weight part.
The curing process of the cyanate/bisoxazoline high-temperature resistance adhesive of a kind of aforesaid method preparation is characterized in that: curing process is 150 ℃/2h+180 ℃/2h+200 ℃/3h, last 220 ℃/5h of aftertreatment.
Beneficial effect
A kind of cyanate/bisoxazoline high-temperature resistance adhesive that the present invention proposes and preparation method thereof You Yu oxazoline compound is the unsaturated five member ring heterocyclic compound that a class contains nitrogen, two atoms of oxygen, Han You oxazoline ring in its molecular structure, all the ring-opening polymerization of the Hang oxazoline ring of Ke Jin is a kind of multi-functional reactive monomer.The chemical property of bisoxazoline compound is the most active and most widely used general, is a kind of good chainextender and coupling agent, can not produce by product and be commonly used for the reactive polymer auxiliary agent in the process of carrying out add-on type chemistry chain extension.The consistency of bisoxazoline compound and CE monomer and BMI monomer is good.Bisoxazoline (BO) compound is joined adhesive system for this reason, play the consistency of improving each component of adhesive system and with chemical group in the tackiness agent chemical chain extending reaction occurs, thereby improve the properties of tackiness agent.
Good of consistency that the invention has the advantages that: bisoxazoline compound and CE monomer and BMI monomer joins adhesive system Jiang bisoxazoline (BO) compound, play the consistency of improving each component of adhesive system and with chemical group in the tackiness agent chemical chain extending reaction occurs, thereby improve the properties of tackiness agent.The thermotolerance of this tackiness agent and dielectric properties are better simultaneously, exceed much than conventional and epoxy binder modified, and the development of Aeronautics and Astronautics is had very high use value.
Embodiment
Now the invention will be further described in conjunction with the embodiments:
Embodiment 1
Take by weighing 40 parts of bisphenol A cyanate esters (BADCy) in there-necked flask, be heated to melting, then add 20 part 4,4 '-ditane type bismaleimides heated and stirred is at 120～200 ℃ of reaction 10min～100min; With 40 parts of N, N '-dimethyl formamide, 5 parts of AG-80 Resins, epoxy and 10 parts of Resins, epoxy that TDE-85 Resins, epoxy mix and blend obtains diluting; Then adjust the temperature to 60～120 ℃, the Resins, epoxy that under this temperature, will dilute and 5 part 2,2 '-(1,3-phenylene)-bisoxazolines are poured into condensing reflux in the there-necked flask, and melting copolymerization 20min～70min, namely obtain cyanate/bisoxazoline high-temperature resistance adhesive.Its curing process is: 150 ℃/2h+180 ℃/2h+200 ℃/3h, and last 220 ℃/5h of aftertreatment.
Embodiment 2
Take by weighing 40 parts of bisphenol A cyanate esters (BADCy) in there-necked flask, be heated to melting, then add 25 part 4,4 '-ditane type bismaleimides heated and stirred is at 120～200 ℃ of reaction 10min～100min; With 20 parts of N, N '-dimethyl formamide, 20 parts of dimethylbenzene, 5 parts of AG-80 Resins, epoxy and 5 parts of Resins, epoxy that TDE-85 Resins, epoxy mix and blend obtains diluting; Then adjust the temperature to 60～120 ℃, the Resins, epoxy that under this temperature, will dilute and 10 part 2,2 '-(1,3-phenylene)-bisoxazolines are poured into condensing reflux in the there-necked flask, and melting copolymerization 20min～70min, namely obtain cyanate/bisoxazoline high-temperature resistance adhesive.Its curing process is: 150 ℃/2h+180 ℃/2h+200 ℃/3h, and last 220 ℃/5h of aftertreatment.
Embodiment 3
Take by weighing 40 parts of bisphenol A cyanate esters (BADCy) in there-necked flask, be heated to melting, then add 30 part 4,4 '-ditane type bismaleimides heated and stirred is at 120～200 ℃ of reaction 10min～100min; With 20 parts of N, N '-dimethyl formamide, 20 parts of dimethylbenzene and 10 parts of Resins, epoxy that TDE-85 Resins, epoxy mix and blend obtains diluting; Then adjust the temperature to 60～120 ℃, the Resins, epoxy that under this temperature, will dilute and 15 part 2,2 '-(1,3-phenylene)-bisoxazolines are poured into condensing reflux in the there-necked flask, and melting copolymerization 20min～70min, namely obtain cyanate/bisoxazoline high-temperature resistance adhesive.Its curing process is: 150 ℃/2h+180 ℃/2h+200 ℃/3h, and last 220 ℃/5h of aftertreatment.
Embodiment 4:
Take by weighing 40 parts of bisphenol A cyanate esters (BADCy) in there-necked flask, be heated to melting, then add 15 part 4,4 '-ditane type bismaleimides heated and stirred is at 120～200 ℃ of reaction 10min～100min; With 20 parts of N, N '-dimethyl formamide, 20 parts of dimethylbenzene and 10 parts of Resins, epoxy that AG-80 Resins, epoxy mix and blend obtains diluting; Then adjust the temperature to 60～120 ℃, the Resins, epoxy that under this temperature, will dilute and 15 part 2,2 '-(1,3-phenylene)-bisoxazolines are poured into condensing reflux in the there-necked flask, and melting copolymerization 20min～70min, namely obtain cyanate/bisoxazoline high-temperature resistance adhesive.Its curing process is: 150 ℃/2h+180 ℃/2h+200 ℃/3h, and last 220 ℃/5h of aftertreatment.
Embodiment 5:
Take by weighing 40 parts of bisphenol A cyanate esters (BADCy) in there-necked flask, be heated to melting, then add 40 part 4,4 '-ditane type bismaleimides heated and stirred is at 120～200 ℃ of reaction 10min～100min; With 20 parts of N, N '-dimethyl formamide, 10 parts of dimethylbenzene, 10 parts of pimelinketone, 10 parts of AG-80 Resins, epoxy and 10 parts of Resins, epoxy that TDE-85 Resins, epoxy mix and blend obtains diluting; Then adjust the temperature to 60～120 ℃, the Resins, epoxy that under this temperature, will dilute and 15 part 2,2 '-(1,3-phenylene)-bisoxazolines are poured into condensing reflux in the there-necked flask, and melting copolymerization 20min～70min, namely obtain cyanate/bisoxazoline high-temperature resistance adhesive.Its curing process is: 150 ℃/2h+180 ℃/2h+200 ℃/3h, and last 220 ℃/5h of aftertreatment.
The performance index of cyanate/bisoxazoline high-temperature resistance adhesive after smear solidifies of this enforcement preparation are as follows:
Under the normal temperature condition: tensile shear strength 〉=20MPa; Room temperature shearing impact intensity (steel) 〉=12kJ/m
2Specific inductivity (50HZ)≤3.4; Dielectric loss factor (50HZ)≤0.009;
Under 200 ℃ of hot conditionss: tensile shear strength 〉=15MPa; Specific inductivity (50HZ)≤3.2; Dielectric loss factor (50HZ)≤0.007;
Storage period 〉=3 month
Comparative Examples
Take by weighing 40 parts of bisphenol A cyanate esters (BADCy) in there-necked flask, be heated to melting, then add 20 part 4,4 '-ditane type bismaleimides heated and stirred is at 120～200 ℃ of reaction 10min～100min; With 20 parts of N, N '-dimethyl formamide, 20 parts of dimethylbenzene, 10 parts of AG-80 Resins, epoxy and 10 parts of Resins, epoxy that TDE-85 Resins, epoxy mix and blend obtains diluting; Then adjust the temperature to 60～120 ℃, the Resins, epoxy that will dilute under this temperature is poured into condensing reflux in the there-necked flask, and melting copolymerization 20min～70min, namely obtains the cyanate high-temperature resistance adhesive that cyanate does not contain bisoxazoline.Its curing process is: 150 ℃/2h+180 ℃/2h+200 ℃/3h, and last 220 ℃/5h of aftertreatment.The result of the high-temperature resistance adhesive of test is: room temperature tensile shearing resistance 19MPa, 200 ℃ of tensile shear strength 10.8MPa; Under frequency 50HZ, the specific inductivity under the room temperature is 3.7, and dielectric loss factor is 0.013; Under frequency 50HZ, the specific inductivity under 200 ℃ is 3.5, and dielectric loss factor is 0.011; Room temperature shearing impact intensity is 8.9kJ/m
2
The comparison of embodiment and Comparative Examples, can find out the adding of bisoxazoline compound, effectively raise cyanate/bisoxazoline high-temperature resistance adhesive tensile shear strength and shearing impact intensity at room temperature, especially the tensile shear strength performance of this tackiness agent is largely increased under hot conditions; Specific inductivity and dielectric loss factor have been reduced simultaneously.
Claims (8)
1. cyanate/bisoxazoline high-temperature resistance adhesive is characterized in that component is: 5～30 parts of 20～50 parts of cyanate ester resins, 10～40 parts of bimaleimide resins, 1～20 part of bisoxazoline compound and Resins, epoxy also comprise 3～40 parts of solvents; Described umber is weight part.
2. cyanate/bisoxazoline high-temperature resistance adhesive according to claim 1, it is characterized in that: described cyanate ester resin is a kind of in bisphenol A cyanate ester resin, Novolac Cyanate Ester Resins, bis-phenol M type cyanate ester resin or the line style Novolac Cyanate Ester Resins, or its many persons' mixture.
3. cyanate/bisoxazoline high-temperature resistance adhesive according to claim 1, it is characterized in that: described bimaleimide resin is any in ditane type bismaleimides, a penylene bismaleimides, diphenyl ether type bismaleimides, diallyl type bismaleimides, diamino-anthraquinone bismaleimides or the oxadiazole structure to prolong type bimaleimide resin, or its many persons' mixture.
4. cyanate/bisoxazoline high-temperature resistance adhesive according to claim 1, it is characterized in that: described bisoxazoline compound is 2,2 '-(1, the 4-phenylene)-bisoxazolines or 2,2 '-(1,3-phenylene)-bisoxazolines, or both mixtures.
5. cyanate/bisoxazoline high-temperature resistance adhesive according to claim 1, it is characterized in that: described Resins, epoxy is any in E-51 Resins, epoxy, E-44 Resins, epoxy, AG-80 Resins, epoxy, TDE-85 Resins, epoxy or the bisphenol A type epoxy resin, or its many persons' mixture.
6. cyanate/bisoxazoline high-temperature resistance adhesive according to claim 1, it is characterized in that: described solvent is any in dehydrated alcohol, dimethyl formamide, dimethylbenzene, pimelinketone, N,N-DIMETHYLACETAMIDE or the trieline, or its many persons' mixture.
7. method for preparing such as claim 1～6 cyanate/bisoxazoline high-temperature resistance adhesive as described in each is characterized in that step is as follows:
Step 1: 20～50 parts of cyanate ester resins and 10～40 parts of bimaleimide resins are put into there-necked flask or reactor, and melting and copolymer-1 0min～100min under 120～200 ℃ temperature obtain cyanate/bimaleimide resin performed polymer;
Step 2: the solvent of 5～30 parts Resins, epoxy and 3～40 parts is at room temperature stirred, Resins, epoxy is dissolved in the solvent fully, the Resins, epoxy after obtaining diluting;
Step 3: then the cyanate of step 1 preparation/bimaleimide resin performed polymer is reduced temperature to 60～120 ℃, the Resins, epoxy of step 2 and 1～20 part of De bisoxazoline compound join condensing reflux in cyanate/bismaleimides performed polymer, and melting copolymerization 20min～70min, obtain cyanate/bisoxazoline high-temperature resistance adhesive;
Umber in the above-mentioned steps is weight part.
8. the curing process of the cyanate of a claim 7 preparation/bisoxazoline high-temperature resistance adhesive is characterized in that: curing process is 150 ℃/2h+180 ℃/2h+200 ℃/3h, last 220 ℃/5h of aftertreatment.
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Cited By (3)
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| CN108264875A (en) * | 2018-02-12 | 2018-07-10 | 成都理工大学 | A kind of resistance to 150 DEG C of high temperature adhesives and preparation method thereof |
| CN112480669A (en) * | 2020-11-05 | 2021-03-12 | 航天特种材料及工艺技术研究所 | High-toughness and high-temperature-resistant bismaleimide resin and preparation method thereof |
| CN113185940A (en) * | 2021-06-17 | 2021-07-30 | 广东中晨电子新材料有限公司 | Insulating glue film composition and application thereof in printed circuit board |
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| CN101570599A (en) * | 2009-05-26 | 2009-11-04 | 同济大学 | Cyanate/bisoxazoline co-cured resin and preparation method and application thereof |
| CN101597371A (en) * | 2009-05-26 | 2009-12-09 | 同济大学 | High-ductility co-cured resin of cyanate and preparation method thereof, application |
| WO2011130188A2 (en) * | 2010-04-13 | 2011-10-20 | Henkel Corporation | Curable compositions, processes for using such compositions to prepare composites and processes for preparing composites having superior surface finish and high fiber consolidation |
| CN102417808A (en) * | 2011-09-29 | 2012-04-18 | 西北工业大学 | High-temperature-resistant adhesive and preparation method thereof |
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| CN101570599A (en) * | 2009-05-26 | 2009-11-04 | 同济大学 | Cyanate/bisoxazoline co-cured resin and preparation method and application thereof |
| CN101597371A (en) * | 2009-05-26 | 2009-12-09 | 同济大学 | High-ductility co-cured resin of cyanate and preparation method thereof, application |
| WO2011130188A2 (en) * | 2010-04-13 | 2011-10-20 | Henkel Corporation | Curable compositions, processes for using such compositions to prepare composites and processes for preparing composites having superior surface finish and high fiber consolidation |
| CN102417808A (en) * | 2011-09-29 | 2012-04-18 | 西北工业大学 | High-temperature-resistant adhesive and preparation method thereof |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108264875A (en) * | 2018-02-12 | 2018-07-10 | 成都理工大学 | A kind of resistance to 150 DEG C of high temperature adhesives and preparation method thereof |
| CN112480669A (en) * | 2020-11-05 | 2021-03-12 | 航天特种材料及工艺技术研究所 | High-toughness and high-temperature-resistant bismaleimide resin and preparation method thereof |
| CN113185940A (en) * | 2021-06-17 | 2021-07-30 | 广东中晨电子新材料有限公司 | Insulating glue film composition and application thereof in printed circuit board |
| CN113185940B (en) * | 2021-06-17 | 2021-12-03 | 广东中晨电子新材料有限公司 | Insulating glue film composition and application thereof in printed circuit board |
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Application publication date: 20130116 |