CN103740104B - The preparation method of securing member composite polyimide material - Google Patents

The preparation method of securing member composite polyimide material Download PDF

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Publication number
CN103740104B
CN103740104B CN201310739971.3A CN201310739971A CN103740104B CN 103740104 B CN103740104 B CN 103740104B CN 201310739971 A CN201310739971 A CN 201310739971A CN 103740104 B CN103740104 B CN 103740104B
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preparation
polyimide material
securing member
aromatic dianhydride
composite polyimide
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CN103740104A (en
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王名辉
邱孜学
包来燕
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SHANGHAI PLASTICS RESEARCH INSTITUTE Co.,Ltd.
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SHANGHAI INST OF SYNTHETIC RESIN
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K9/00—Use of pretreated ingredients
    • C08K9/04—Ingredients treated with organic substances
    • C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
    • 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
    • C08G73/124—Unsaturated polyimide precursors the unsaturated precursors containing oxygen in the form of ether bonds in the main chain
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/02—Fibres or whiskers
    • C08K7/04—Fibres or whiskers inorganic
    • C08K7/06—Elements
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/02—Fibres or whiskers
    • C08K7/04—Fibres or whiskers inorganic
    • C08K7/14—Glass

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Reinforced Plastic Materials (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

The present invention relates to the preparation method of a kind of securing member composite polyimide material, polyimid-base resin preparation process is: first with ethanol respectively with mix aromatic dianhydride generation esterification, anhydride esterifying adds 4 after terminating, and 4' diaminodiphenyl ether carries out polycondensation reaction；Then carry out end capping reaction with 5 norborene 2,3 dicarboxylic acid monoethylester and generate oligomer, the more glass fiber impregnated kneading processed with organo-silicon coupling agent；Followed by, heat treatment prepares polyimides prepreg, carries out hot-forming producing required product；The self-locking fastener performance wherein prepared is: screw thread bearing capacity 11KN, tensile failure power 2.9kN；Charge ratio is: mixing aromatic dianhydride, 4, each 1mol of 4' diaminodiphenyl ether, 5 norbornadiene 2,3 dicarboxylic acid anhydride 0.25～0.75mol.They are when ethanol is esterified, and acid anhydride is 1:4～10 with the mol ratio of alcohol, reaction temperature 69～90 DEG C, response time 2～5 hours.

Description

The preparation method of securing member composite polyimide material
One, technical field
The present invention relates to the preparation method of securing member composite polyimide material, more precisely by a-ODPA and other Dianhydride monomer adds 4 after being esterified in alcoholic solution, 4'-diaminodiphenyl ether generation polycondensation reaction, and with the fall ice being esterified equally Sheet enedioic acid acid anhydride blocks, and polyimides pre-preg material made by followed by impregnated glass fiber or carbon fiber；Ultimately form securing member to use The preparation method of composite polyimide material.
Two, background technology
So-called securing member means and two or more parts or component fastens type part used when linking together General name.Such as bolt, nut, packing ring, screw, pin, rivet etc..Tight prepared by composite polyimide material prepared by the present invention Firmware refers to screwed self-locking securing member.Such as bolt, nut, screw rod and screw etc..
5-norborene-2, the polyimides that 3-dicarboxylic anhydride (NA) blocks is mainly used in composite, as made lamination Plate, structure member and high temperature resistant and insulated product.Aspect in terms of aircraft and electrical equipment, is used for making air-distribution engines engine zero Part, circuit board, click slot wedge, stator and rotor insulation side plate etc..It also is used as adhesive.In view of mechanical strength, thermally-stabilised Property and processing and price factor, few for the report of securing member.
PMMI Vespel moulding compound, life-time service temperature is up to 288 DEG C, and heatproof reaches 480 DEG C in short-term, tool There are low temperature coefficient of friction and high abrasion resistance properties, coarse vacuum degassing, low particle to produce and intrinsic purity, have been used for making spiral shell Nail, bolt, nut, threaded rod, packing ring etc..Automobile, machinery, process equipment, Aero-Space and semiconductor applications are applied.But It is that processing and forming difficulty needs again through operations such as car, milling and upper screw threads, relatively costly.
The polyimide material of practical self-locking securing member is provided, really needs research and development with great concentration, ability New material, new product is contributed for high-technology field.
Three, summary of the invention
The polyimide material of self-locking securing member, the material of the most small-sized bolt processing, the most domestic still lack this Plant polyimide material.The present inventors are through particular study, it is provided that product is practical for user, has filled up domestic blank.It Complete skill scheme as follows:
Securing member composite polyimide material has a following macromolecule repetitive:
In formula, m:n=1:0.3～3, m+n=1.3～4
This composite polyimide material the processing step of preparation method include: the preparation of polyimid-base resin: First with ethanol respectively with mix aromatic dianhydride, 5-norborene-2,3-dicarboxylic anhydride generation esterification；Mixing aromatic dianhydride Esterification adds 4,4'-diaminodiphenyl ether after terminating and carries out polycondensation reaction；Then with 5-norborene-2,3-diformate mono Ethyl ester carries out end capping reaction and generates oligomer polyimid-base resin；Polyimid-base resin again with organo-silicon coupling agent at The glass fibre managed or impregnated carbon fiber are mediated；Followed by, heat treatment prepares polyimides pre-preg material, carries out hot-forming system Take required product；The self-locking fastener performance wherein prepared is: screw thread bearing capacity 11KN, tensile failure power 2.9kN；Charge ratio For: mixing aromatic dianhydride monomer is 1:0.3～3 with the mol ratio of 4,4'-diaminodiphenyl ether；Mixing aromatic dianhydride monomer and 5- The mol ratio of norbornadiene 2,3-dicarboxylic acid anhydride is 1:0.25～0.75；During esterification, mixing aromatic dianhydride monomer and second The mol ratio of alcohol is 1:4～10,5-norborene-2, and 3-dicarboxylic anhydride is 1:4～10 with the mol ratio of ethanol, esterification temperature Spend 69～90 DEG C, response time 2～5 hours.
Heretofore described mixing aromatic dianhydride be 2,3,3', 4'-diphenyl ether tetraformic dianhydride with selected from 3,3', 4, 4'-bisphenol-A diphenyl ether tetraformic dianhydride, 3,3', 4,4'-bibenzene tetracarboxylic dianhydride, 2,3', 4,4'-bibenzene tetracarboxylic dianhydride, 3, A kind of mixture in 4,3', 4'-diphenyl ether tetraformic dianhydride or pyromellitic acid anhydride.
Heretofore described mixing aromatic dianhydride is preferably 2,3,3', 4'-diphenyl ether tetraformic dianhydride and 3,3', and 4, The mixture of 4'-bisphenol-A diphenyl ether tetraformic dianhydride, wherein 2,3,3', 4'-diphenyl ether tetraformic dianhydride and 3,3', 4,4'-is double The mol ratio of phenol A diphenyl ether tetraformic dianhydride is 1:0.6～1.0；Mixing aromatic dianhydride monomer and 5-norbornadiene 2,3-bis- The mol ratio of formic anhydride is 1.6～2.0:1.5；Mixing aromatic dianhydride monomer is 1.6 with the mol ratio of 4,4'-diaminodiphenyl ether ～2.0:2.0.
Heretofore described organo-silicon coupling agent is selected from γ aminopropyltriethoxy silane, γ-glycidyl oxygen A kind of in propyl trimethoxy silicane or their mixture；Described heat treatment prepares at the heat of polyimides pre-preg material Reason process is via 80 DEG C/3h, 160 DEG C/2h, prepares polyimides pre-preg material after 230 DEG C/1h.
The hot-forming condition of heretofore described polyimides pre-preg material is 310～330 DEG C/4MPa, during hot pressing Between with test specimen size, depending on thickness.
Heretofore described glass fibre or 10 weight %～55 that carbon fiber consumption is composite polyimide material weight Weight %.
If heretofore described polyimides pre-preg material is molded directly into type bolt, nut, processing temperature is still 310 ～330 DEG C/4Mpa.The screw thread bearing capacity obtained is 11KN, and the tensile failure power of bolt is 2.9KN.
The composite polyimide material prepared according to the present invention, has 5-norborene-2, and 3-dicarboxylic acid anhydride (NA) blocks Or 5-norborene-2, all features of the composite polyimide material that 3-dicarboxylic acid monoethylester (NE) blocks, i.e. NA end-blocking is poly- Acid imide pre-impregnating process is simple, and pre-preg material stable performance, pressing Heat stability is good, life-time service temperature is 260 DEG C ～300 DEG C, and satisfactory mechanical property goes, its laminate porosity low (＜ 2%), and general lamination process processes can be used. More valuable is processing and forming good fluidity, and curing rate can directly mold bolt soon, can process stove bolt, bolt tension especially Destructive power is 2.9KN, and screw thread bearing capacity is 11KN.
Four, detailed description of the invention
In order to preferably implement the present invention, especially exemplified by embodiment, it is described, but embodiment is no limitation of the present invention.
Embodiment 1
(1) preparation of mono-acid ester
246g(1.5mol) 5-norborene-2,3-dicarboxylic acid anhydride in 259g ethanol 69 DEG C～90 DEG C to be heated to reflux 2 little Time prepare 5-norborene-2,3-dicarboxylic acid monoethylester (NE).
286g(1mol) 2,3,3', 4'-diphenyl ether tetraformic dianhydride is little with 69～90 DEG C of back flow reaction 5 in 256g ethanol Time prepare 2,3,3', 4'-diphenyl ether tetraformic mono ethyl ester.
514g(1mol) 3,3', 4,4'-bisphenol-A diphenyl ether tetraformic dianhydride in 463g ethanol with 71 DEG C～90 DEG C heating Reflux 2 hours prepared 3,3', 4,4'-bisphenol-A diphenyl ether tetraformic mono ethyl ester.
(2) preparation of polyimid-base resin
400g(2mol) 4,4'-diaminodiphenyl ether is dissolved in 358g ethanol and stirs half an hour, then, adds above-mentioned system Standby 2,3,3', 4'-diphenyl ether tetraformic mono ethyl ester and 3,3', in 4,4'-bisphenol-A diphenyl ether tetraformic mono ethyl ester mixture, After stirring 1～2 hour, with 5-norborene-2,3-dicarboxylic acid monoethylester (NE), 70 DEG C～83 DEG C stirring reactions 5 hours, obtains Obtain solution of polyimid-base resin.
(3) preparation of polyimides pre-preg material
160g is glass fiber impregnated at polyamides with what organo-silicon coupling agent γ aminopropyltriethoxy silane processed In imine matrix resin solution, through fully mediating, via 80 DEG C/3h, 160 DEG C/2h, 230 DEG C/1h heat treatment acquisition polyamides Asia Amine pre-preg material.
(4) preparation of composite product
Polyimides pre-preg material is under 310～330 DEG C/4MPa, and hot-press solidifying obtains required product.
The heat distortion temperature of composite hot pressing part is 312 DEG C, hot strength 52.4MPa, bending strength 118MPa.
Direct is still 310～330 DEG C/4MPa with polyimides pre-preg material compression molding bolt, nut, condition of molding, Then being derived from locking-type securing member, its screw thread bearing capacity is 11KN, and bolt tension destructive power is 2.9KN.
Embodiment 2
Except 2,3,3', the consumption of 4'-diphenyl ether tetraformic dianhydride is 1mol, 3,3', 4,4'-bisphenol-A diphenyl ether tetraformics Dianhydride consumption is 0.6mol, and solution of polyimid-base resin preparation is by 5-norborene-2,3-diacid mono ethyl ester, 2,3, The ethanol solution of 3', 4'-diphenyl ether tetraformic mono ethyl ester and 3,3', 4,4'-bisphenol-A tetracarboxylic acid mono ethyl ester and 4,4'-diaminourea The ethanol solution hybrid reaction of diphenyl ether；The glass fibers that organo-silicon coupling agent γ aminopropyltriethoxy silane was processed Dimension is immersed in prepared solution of polyimid-base resin, and other formula is the same with embodiment 1 with operating procedure, result screw thread Bearing capacity be 10KN bolt tension destructive power be 2.5KN.
Embodiment 3
In addition to replacing glass fibre with carbon fiber, other formula is the same with embodiment 1 with operating procedure, and result screw thread carries Power 13KN, bolt tension destructive power is 3.1KN.

Claims (6)

1. the preparation method of a securing member composite polyimide material, it is characterised in that polyimid-base resin has The structure of following macromolecule repetitive:
In formula, m: n=1: 0.3～3, m+n=1.3～4
The processing step of this composite polyimide material preparation method includes: the preparation of polyimid-base resin: first use second Alcohol respectively with mix aromatic dianhydride, 5-norborene-2,3-dicarboxylic anhydride generation esterification；Mixing aromatic dianhydride esterification Add 4，4′-diaminodipohenyl ether after end and carry out polycondensation reaction；Then with 5-norborene-2,3-dicarboxylic acid monoethylester is carried out End capping reaction generates oligomer polyimid-base resin；The glass that polyimid-base resin processed with organo-silicon coupling agent again Glass fiber or impregnated carbon fiber are mediated；Followed by, heat treatment prepares polyimides pre-preg material, carry out hot-forming produce required Product；The self-locking fastener performance wherein prepared is: screw thread bearing capacity 11KN, tensile failure power 2.9kN；Charge ratio is: mixing Aromatic dianhydride monomer is 1: 0.3～3 with the mol ratio of 4，4′-diaminodipohenyl ether；Mixing aromatic dianhydride monomer and 5-norborneol Diene 2, the mol ratio of 3-dicarboxylic acid anhydride is 1: 0.25～0.75；During esterification, mixing aromatic dianhydride monomer is rubbed with ethanol Your ratio is 1: 4～10,5-norborene-2, and the mol ratio of 3-dicarboxylic anhydride and ethanol is 1: 4～10, esterification reaction temperature 69～ 90 DEG C, response time 2～5 hours.
The preparation method of a kind of securing member composite polyimide material the most according to claim 1, it is characterised in that institute The mixing aromatic dianhydride stated is 2,3,3 ', 4 '-diphenyl ether tetraformic dianhydride with selected from 3,3 ', 4,4 '-bisphenol-A diphenyl ether tetraformic A kind of mixture in dianhydride or pyromellitic acid anhydride.
The preparation method of a kind of securing member composite polyimide material the most according to claim 1 and 2, its feature exists In, described mixing aromatic dianhydride is 2,3,3 ', 4 '-diphenyl ether tetraformic dianhydride and 3,3 ', 4, and 4 '-bisphenol-A diphenyl ether tetramethyl The mixture of acid dianhydride, wherein 2,3,3 ', 4 '-diphenyl ether tetraformic dianhydride and 3,3 ', 4,4 '-bisphenol-A diphenyl ether tetraformic two The mol ratio of acid anhydride is 1: 0.6～1.0；Mixing aromatic dianhydride monomer and 5-norbornadiene 2, the mol ratio of 3-dicarboxylic acid anhydride is 1.6～2.0: 1.5；Mixing aromatic dianhydride monomer is 1.6～2.0: 2.0 with the mol ratio of 4，4′-diaminodipohenyl ether.
The preparation method of a kind of securing member composite polyimide material the most according to claim 1, it is characterised in that institute The organo-silicon coupling agent stated is in γ aminopropyltriethoxy silane, γ-glycidoxypropyltrimethoxy base silane A kind of or their mixture；Described heat treatment prepare the heat treatment process of polyimides pre-preg material be via 80 DEG C/ 3h, prepares polyimides pre-preg material by 160 DEG C/2h after 230 DEG C/1h.
The preparation method of a kind of securing member composite polyimide material the most according to claim 1, it is characterised in that institute The hot-forming condition of the polyimides pre-preg material stated is 310～330 DEG C/4MPa, hot pressing time with test specimen size, thickness and Fixed.
The preparation method of a kind of securing member composite polyimide material the most according to claim 1, it is characterised in that institute The glass fibre stated or 10 weight % that carbon fiber consumption is composite polyimide material weight～55 weight %.
CN201310739971.3A 2013-12-27 2013-12-27 The preparation method of securing member composite polyimide material Active CN103740104B (en)

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Publication number Priority date Publication date Assignee Title
CN108395535A (en) * 2018-04-03 2018-08-14 上海市合成树脂研究所有限公司 A kind of imido preparation method of hot polymerization for laminated product

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6303744B1 (en) * 2000-03-23 2001-10-16 The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration Polyimides and process for preparing polyimides having improved thermal-oxidative stability
CN101654518A (en) * 2009-09-23 2010-02-24 中国科学院化学研究所 Thermosetting polyimide resin and preparation method and application thereof
WO2010087918A1 (en) * 2009-01-31 2010-08-05 General Electric Company Autoclave cure cycle design process and curing method

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6303744B1 (en) * 2000-03-23 2001-10-16 The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration Polyimides and process for preparing polyimides having improved thermal-oxidative stability
WO2010087918A1 (en) * 2009-01-31 2010-08-05 General Electric Company Autoclave cure cycle design process and curing method
CN101654518A (en) * 2009-09-23 2010-02-24 中国科学院化学研究所 Thermosetting polyimide resin and preparation method and application thereof

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Address after: 200235 No. 36, Xuhui District, Shanghai, Caobao Road

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