CN103992640B - Diazanaphthalene terphenyl structure polyarylether toughening modifying BMI blending resin and preparation method thereof - Google Patents
Diazanaphthalene terphenyl structure polyarylether toughening modifying BMI blending resin and preparation method thereof Download PDFInfo
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- CN103992640B CN103992640B CN201410220137.8A CN201410220137A CN103992640B CN 103992640 B CN103992640 B CN 103992640B CN 201410220137 A CN201410220137 A CN 201410220137A CN 103992640 B CN103992640 B CN 103992640B
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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
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08L79/085—Unsaturated polyimide precursors
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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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/12—Unsaturated polyimide precursors
- C08G73/126—Unsaturated polyimide precursors the unsaturated precursors being wholly aromatic
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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
Abstract
The invention belongs to polymeric material field, it is related to a kind of diazanaphthalene terphenyl structure polyarylether toughening modifying BMI blending resin and preparation method thereof.The raw material of the blending resin includes following components, and fraction by weight is calculated as：BMI：100 parts；Allyl compound：5~85 parts；Diazanaphthalene terphenyl structure polyarylether resin：1~30 part.The preparation method of the diazanaphthalene terphenyl structure polyarylether toughening modifying BMI blending resin：Blending resin pre-composition is prepared using solwution method or fusion method first；Next to that the curing molding of blending resin.Such toughness reinforcing BMI blending resins have good impact flexibility, can be as resin matrix, by lamination, molding, RTM techniques, for preparing high temperature resistant, high-performance fiber reinforced resin based composites.
Description
Technical field
The invention belongs to polymeric material field, and in particular to change to a kind of diazanaphthalene terphenyl structure polyarylether toughness reinforcing
Property BMI blending resin and preparation method thereof.
Background technology
Bimaleimide resin (Bismaleimide, abbreviation BMI) is for active end group with maleimide (MI)
Bifunctional compound.BMI has excellent heat resistance, electrical insulating property, radiation hardness, anti-flammability, good mechanical property and chi
The features such as very little stability, it is widely used in Aeronautics and Astronautics, machinery, electronics, the resin matrix of advanced composite material, high temperature resistant
Insulating materials and adhesive etc..Bimaleimide resin monomer can be in autohemagglutination under thermocatalysis, and occurs cross-linking reaction, raw
Into highly cross-linked network.But, crosslink density is high after bimaleimide resin solidification so that the fragility of material is big, resistance to
The ability of impact and stress cracking is poor, it is impossible to meets as the toughness and impact resistance needed for antinoise structure material, limits
It is applied, it is therefore desirable to carry out toughening modifying to it.
The toughening modifying method of conventional BMI resins mainly includes at present：Synthesizing new BMI monomers, addition diamine, rubber
The modification to BMI resins such as glue, allyl compound, thermoplastic resin, thermosetting resin, inorganic nano-particle or carbon fiber.
Result of study shows, by introducing the mode such as flexible group or addition rubber, although can improve BMI resin systems
The toughness of solidfied material, but its modulus and heat resistance can be significantly reduced.Carrying out toughness reinforcing BMI with High performance plastic resin can not drop
The toughness of BMI resins is improved on the premise of low resin heat resistance energy and mechanical property.Conventional thermoplastic resin has polyester
(PET), polyether sulfone (PES), polyether-ketone (PEK), polyimides (PI), polyether-ketone (PEK) etc..It is modified in Toughened With High Performance Thermoplastics
During BMI resins, allyl compound is generally added simultaneously and carries out co-curing behavior, allyl compound is both that toughener is again solid
Agent, is conducive to improving dissolubility of the thermoplastic resin in system, reduces cost, improve the operability and technique of BMI resins
Property, improve the mechanical property of co-mixing system.But, on the one hand, these thermoplastic polymers have that dissolubility is poor, it is common with BMI
The problem of melt viscosity of mixed system is big, causes the processability of BMI resin alloy systems to be deteriorated, while making its cured product surface
The problem of there is skinning, influences the mechanical property of product.On the other hand, allyl compound conventional at present is mainly O, and O '-
Diallyl bisphenol (DABPA), other allyl compound researchs are seldom.Therefore, the new resin of searching and method, realization pair
While BMI resins carry out toughening modifying, its heat resistance can be kept or improve, and good processability can be kept just to have ten
Divide important actual application value.
The resin of polyarylether thermoplast containing diazanaphthalene terphenyl structure is the high property of a class of Dalian University of Technology's independent research
Energy thermoplastic resin, its glass transition temperature controllable between 250~370 DEG C, and it is dissolvable in water some aprotonic polars
Solvent, can not only use the melt-processed mode of traditional thermoplastic resin, can also be processed using solution mode, combination property is excellent
Different, especially mechanical behavior under high temperature is protruded, and is that the toughener and preparation high-performance advanced composite material of thermosetting resin are preferable
Matrix material.Patent of invention related to the present invention has：Patent of invention ZL201110206012.6 discloses a kind of maleimide
Amine end-blocking poly (arylene ether nitrile) containing diazanaphthalene terphenyl structure and preparation method thereof；Patent of invention US5138000 discloses BMI resins
With diallyl '-biphenyl diphenol blending resin and preparation method thereof.Above-mentioned patent is not related to poly- containing diazanaphthalene terphenyl structure
The toughening modifying of aryl oxide and pi-allyl '-biphenyl diphenol to BMI resins.Han Yongjin (BMIs/Phthalazinone PAEK
The structure and performance of blend, Dalian University of Technology, master's thesis, 2009) disclose amino-terminated containing benzodiazine
Ketone biphenyl structural PAEK (PPEK-DA)/DABPA/BDM blending resin systems；Jiang Hailong (bimaleimide resins/official
The structure and performance of the polyethersulfone blended body of Phthalazinone, Dalian University of Technology, master's thesis, 2010 can be changed) disclose
Amino-terminated polyether sulphone containing diazanaphthalene terphenyl structure (PPES-DA)/DABPA/BDM blending resin systems；Long Huan of Shangguan
(research of Phthalazinone polyarylether modified bismaleimide resin, Dalian University of Technology, master's thesis, 2011) is public
The ketone of poly (arylene ether nitrile) containing diazanaphthalene terphenyl structure (PPENK), amino-terminated copolymerization aryl ether ketone (PPBEK-DA) are opened right
What is used in BMI co-mixing systems disclosed in DABPA/BDM toughness reinforcing blending and modifyings, but above-mentioned three documents is DABPA conducts
Curing agent, is not related to diallyl '-biphenyl diphenol (DABP).Compared with disclosed document, this patent is simultaneously using containing diaza
Naphthalenone biphenyl structural polyarylether thermoplast resin and DABP carry out toughening modifying to BMI resins, on the one hand, containing phthalazone connection
Benzene structure polyarylether thermoplast resin can improve the impact flexibility of BMI resins, and keep excellent heat resistance；On the other hand,
Compared with DABPA, DABP is more advantageous in terms of processing fluidity, heat resistance and the impact flexibility of co-mixing system is improved.
In summary, foregoing invention and document are not directed to the increasing of the resin of polyarylether thermoplast containing diazanaphthalene terphenyl structure
Tough modified DABP/BMI blending resins and its preparation method.On the resin toughening of polyarylether thermoplast containing diazanaphthalene terphenyl structure
Modified DABP/BMI blending resins and its preparation method are not found in relevant patented technology report, also not at home and abroad in public publication
Occur.
The content of the invention
The technical problem to be solved in the present invention be with the high-temperature resistant thermoplastic resin of polyarylether containing diazanaphthalene terphenyl structure,
Diallyl '-biphenyl diphenol (DABP) carries out toughening modifying to BMI resins, improves processing fluidity, the reduction of BMI blending resins
The surface skining phenomenon of solidfied material, the impact flexibility for improving blending resin solidfied material.While there is provided a kind of simplicity, being easy to behaviour
The preparation method of the diazanaphthalene terphenyl structure polyarylether toughening modifying BMI blending resin of work.
A kind of diazanaphthalene terphenyl structure polyarylether toughening modifying BMI blending resin, the blending resin
Raw material includes following components, and fraction by weight is calculated as：
BMI：100 parts；
Allyl compound：5~85 parts；
Diazanaphthalene terphenyl structure polyarylether resin：1~30 part.
Described BMI is：
One or both of it is mixed above.
Diallyl '-biphenyl diphenol, the structural formula of diallyl '-biphenyl diphenol must be contained in described allyl compound
For：
Or contain other diallyl compounds simultaneously, it is as follows：
One or more kinds of mixing.
The structural formula of described diazanaphthalene terphenyl structure polyarylether resin is：
In one or more of mixing；
Wherein, R1、R2、R3、R4It is hydrogen, halogenic substituent, phenyl, phenoxy group, alkyl or alkoxy, alkyl or alkoxy
All contain at least one carbon atom, R1、R2、R3And R4Structure it is identical or different；M >=3, n >=0；
Ar1、Ar3It is following middle one or more kinds of mixing for the agent structure of double halogen monomers：
R is hydrogen, methoxyl group, phenyl, alkyl or alkoxy, and wherein alkyl or alkoxy all contains at least one carbon atom；
Ar2It is following middle one or more kinds of mixing for the agent structure of biphenol monomer：
1,2,1,3 or Isosorbide-5-Nitrae position；
2,2 ' positions or 4,4 ' positions；
Isosorbide-5-Nitrae position, 1,5,1,6,2,6 or 2,7；
3,3 ' positions or 4,4 ' positions；
3,3 ' positions or 4,4 ' positions；
3,3 ' positions or 4,4 ' positions；
3,3 ' positions or 4,4 ' positions；
3,3 ' positions or 4,4 ' positions；
The present invention proposes a kind of diazanaphthalene terphenyl structure polyarylether toughening modifying BMI blending resin
Preparation method, step is as follows：
(1) blending resin pre-composition is prepared using solwution method or fusion method
(a) solwution method
1~30 part of diazanaphthalene terphenyl structure polyarylether resin is dissolved in 65~100 parts of organic solvents, is configured to
Polymer solution；5~85 parts of allyl compounds are heated to melting, above-mentioned polymer solution is added, stirred, temperature is 80
~130 DEG C；Under vacuum, organic solvent is removed；100 parts of BMIs are added, under the conditions of 100~140 DEG C,
Stirring mixing 20~40 minutes, obtains blending resin pre-composition；
(b) fusion method
5~85 parts of allyl compounds are heated to melting, temperature is raised to 100~150 DEG C, adds 1~30 part of diaza
Naphthalenone biphenyl structural polyarylether resin, stirring is dissolved completely in allyl compound until it, then temperature is adjusted to 120~
140 DEG C, 100 parts of BMIs are added, continues to stir 20~40 minutes, obtains blending resin pre-composition；
(2) curing molding of blending resin
Blending resin pre-composition prepared by above-mentioned solwution method or fusion method is carried out under conditions of 90~130 DEG C of vacuum
Vacuum defoamation, it until bubble-free emerges, then solidified 0.5~12 hour at 100~180 DEG C of temperature, cooled down after solidification
To room temperature, diazanaphthalene terphenyl structure polyarylether toughening modifying BMI blending resin is obtained.
Described organic solvent is dimethyl sulfoxide (DMSO), N,N-dimethylformamide, DMAC N,N' dimethyl acetamide, N- methyl pyrroles
One or both of pyrrolidone, chloroform are mixed above.
The effect and benefit of the present invention：Using the high-temperature resistant thermoplastic resin of polyarylether containing diazanaphthalene terphenyl structure and two
Pi-allyl '-biphenyl diphenol is to BMI blending resin toughening modifyings, by adjusting thermoplastic resin in blending resin, diallyl biphenyl
Diphenol and BMI content proportioning, so as to reach the purpose of the performance of regulation and control BMI blending resin systems, are prepared for one kind and have concurrently
The BMI blending resins of high tenacity, excellent heat resistance and good workability.From the performance pair of embodiments of the invention and blending resin
Than (as shown in table 1) as can be seen that the blending resin has higher impact strength and heat resistance than DABP/BMI system, simultaneously
Also there is higher impact strength than diazanaphthalene terphenyl structure polyarylether/DABPA/BMI co-mixing systems.It is of the present invention
Diazanaphthalene terphenyl structure polyarylether toughening modifying BMI blending resin has good molding processibility, can make
For resin matrix, high temperature resistant, high-performance fiber reinforced resin based composites are prepared by lamination, molding, RTM techniques.
The performance comparison of the blending resin system of table 1
Annotation：*Notch impact strength
Embodiment
The present invention is specifically described below by embodiment, it is necessary to it is pointed out here that be that the present embodiment is served only for pair
The present invention's further illustrates, but it is not intended that limitation to this patent protection domain, the person skilled in the art in the field can
To make some nonessential modifications and adaptations according to the content of the invention described above.
Embodiment 1
The amino-terminated sulphone resin of poly (arylene ether nitrile) containing diazanaphthalene terphenyl structure/DABP/BDM blending resins
65gDABP is first weighed, adds in reaction vessel and stirs, temperature is gradually increased to about 80 DEG C, until DABP meltings, is treated
When temperature rises to about 125 DEG C, amino-terminated polyaryl ether-nitrile-sulfone containing diazanaphthalene terphenyl structure (PPENS-DA) 10g is added,
Stirring treats that it is dissolved completely in DABP, and then 100g BMIs diphenyl-methane (BDM) is added in system and continued
Stir about 30 minutes, has obtained the uniform, liquid with certain viscosity, the liquid is poured into mould preheated in advance,
The lab scale of vacuum defoamation about 1 is carried out in 110 DEG C, is emerged to bubble-free, the mould for having taken off bubble is moved into temperature control oven, by following journey
Sequence is solidified：130 DEG C solidify 0.5 hour, and 150 DEG C solidify 2 hours, and 190 DEG C solidify 2 hours, and 230 DEG C solidify 4 hours, solidification
Terminating relief, it naturally cools to room temperature.The notch impact strength of blending resin is 4.98KJ/m2, glass transition temperature 269
℃。
Embodiment 2
Polyaryl ether sulphone resin containing diazanaphthalene terphenyl structure/DABP/DABAP/BDM blending resins
15g diazanaphthalene terphenyl structures polyether sulphone (PPES) is weighed, and is dissolved in configuring in 100mL chloroform
Into polymer solution, weigh 60gDABP and 5gDABPA and add stirring in reaction vessel, temperature is gradually increased to about 80 DEG C, until
DABP and DABPA meltings, when temperature rises to about 125 DEG C, add the polymer solution containing 15gPPES, stirring treats that its mixing is equal
It is even, then 100g BMIs diphenyl-methane (BDM) is added in system and continues stir about 40 minutes, has been obtained uniform
, liquid with certain viscosity, the liquid is poured into mould preheated in advance, it is small to carry out vacuum defoamations about 1 in 130 DEG C
Examination, is emerged to bubble-free, and the mould for having taken off bubble is moved into temperature control oven, solidified by following program：130 DEG C of solidifications 1 are small
When, 160 DEG C solidify 2 hours, and 190 DEG C solidify 2 hours, and 230 DEG C solidify 4 hours, and solidification terminates relief, and it naturally cools to room temperature.
The notch impact strength of blending resin is 4.75KJ/m2,253 DEG C of glass transition temperature.
Embodiment 3
Ketone-grouped resin containing diazanaphthalene terphenyl structure (PPEK)/DABP/BDM blending resins
First weigh 40gDABP and 30gDABPA and add stirring in reaction vessel, temperature is gradually increased to about 80 DEG C, until
DABP and DABPA meltings, when temperature rises to about 125 DEG C, add 15g PPEK, stirring treats that it is well mixed, then by 100g
BMI diphenyl-methane (BDM) is added to continuation stir about 40min in system, has obtained uniformly, with certain viscous
The liquid of degree, the liquid is poured into mould preheated in advance, is carried out the lab scale of vacuum defoamation about 1 in 110 DEG C, is emitted to bubble-free
Go out, the mould for having taken off bubble is moved into temperature control oven, solidified by following program：130 DEG C solidify 0.5 hour, 150 DEG C of solidifications
2 hours, 190 DEG C solidified 2 hours, and 230 DEG C solidify 4 hours, and solidification terminates relief, and it naturally cools to room temperature.Blending resin lack
Mouth impact strength is 4.53KJ/m2,247 DEG C of glass transition temperature.
Claims (5)
1. a kind of diazanaphthalene terphenyl structure polyarylether toughening modifying BMI blending resin, it is characterised in that should
The raw material of blending resin includes following components, is calculated by weight as：
BMI：100 parts；
Allyl compound：65~85 parts；
Diazanaphthalene terphenyl structure polyarylether resin：10~15 parts；
The allyl compound is diallyl '-biphenyl diphenol, and the structural formula of diallyl '-biphenyl diphenol is：
The structural formula of the diazanaphthalene terphenyl structure polyarylether resin is：
In one or more of mixing；
Wherein, R1、R2、R3、R4It is hydrogen, halogenic substituent, phenyl, phenoxy group, alkyl or alkoxy, alkyl or alkoxy all contain
At least one carbon atom, R1、R2、R3And R4Structure it is identical or different；
M >=3, n >=0；
Ar1For
Ar3It is following middle one or more kinds of mixing for the agent structure of double halogen monomers：
R is hydrogen, phenyl, alkyl or alkoxy, and wherein alkyl or alkoxy all contains at least one carbon atom；
Ar2It is following middle one or more kinds of mixing for the agent structure of biphenol monomer：
1,2,1,3 or Isosorbide-5-Nitrae position；
2,2 ' positions or 4,4 ' positions；
Isosorbide-5-Nitrae position, 1,5,1,6,2,6 or 2,7；
3,3 ' positions or 4,4 ' positions；
3,3 ' positions or 4,4 ' positions；
3,3 ' positions or 4,4 ' positions；
3,3 ' positions or 4,4 ' positions；
3,3 ' positions or 4,4 ' positions；
2. diazanaphthalene terphenyl structure polyarylether toughening modifying BMI blending tree according to claim 1
Fat, it is characterised in that described BMI is：
One or both of it is mixed above.
3. diazanaphthalene terphenyl structure polyarylether toughening modifying BMI blending tree according to claim 1
Fat, it is characterised in that in the Ar3In, R is methoxyl group.
4. the diazanaphthalene terphenyl structure polyarylether toughening modifying BMI described in a kind of any one of claim 1-3
The preparation method of blending resin, it is characterised in that step is as follows：
(1) blending resin pre-composition is prepared using solwution method or fusion method
(a) solwution method
10~15 parts of diazanaphthalene terphenyl structure polyarylether resins are dissolved in 65~100 parts of organic solvents, are configured to gather
Polymer solution；65~85 parts of allyl compounds are heated to melting, above-mentioned polymer solution is added, stirred, temperature is 80
~130 DEG C；Under vacuum, organic solvent is removed；100 parts of BMIs are added, under the conditions of 100~140 DEG C,
Stirring mixing 20~40 minutes, obtains blending resin pre-composition；
(b) fusion method
65~85 parts of allyl compounds are heated to melting, temperature is raised to 100~150 DEG C, adds 10~15 parts of benzodiazines
Ketone biphenyl structural polyarylether resin, stirring is dissolved completely in allyl compound until it, then temperature is adjusted into 120~140
DEG C, 100 parts of BMIs are added, continues to stir 20~40 minutes, obtains blending resin pre-composition；
(2) curing molding of blending resin
Blending resin pre-composition prepared by above-mentioned solwution method or fusion method carries out vacuum under conditions of 90~130 DEG C of vacuum
Deaeration, it until bubble-free emerges, then solidified 0.5~12 hour at 100~180 DEG C of temperature, room be cooled to after solidification
Temperature, obtains diazanaphthalene terphenyl structure polyarylether toughening modifying BMI blending resin.
5. preparation method according to claim 4, it is characterised in that described organic solvent is dimethyl sulfoxide (DMSO), N, N-
One or both of dimethylformamide, DMAC N,N' dimethyl acetamide, 1-METHYLPYRROLIDONE, chloroform are mixed above.
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| CN106280449B (en) * | 2016-08-19 | 2019-08-20 | 大连理工大学 | A kind of high tenacity, benzoxazine/diallyl diphenol/bismaleimide blending resin of low viscosity and preparation method thereof |
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