CN103740104A - Preparation method of polyimide composite material of fastening piece - Google Patents
Preparation method of polyimide composite material of fastening piece Download PDFInfo
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- CN103740104A CN103740104A CN201310739971.3A CN201310739971A CN103740104A CN 103740104 A CN103740104 A CN 103740104A CN 201310739971 A CN201310739971 A CN 201310739971A CN 103740104 A CN103740104 A CN 103740104A
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- preparation
- dianhydride
- fastening piece
- diphenyl ether
- polyimide
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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
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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
- C08G73/124—Unsaturated polyimide precursors the unsaturated precursors containing oxygen in the form of ether bonds in the main chain
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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
- C08K7/00—Use of ingredients characterised by shape
- C08K7/02—Fibres or whiskers
- C08K7/04—Fibres or whiskers inorganic
- C08K7/06—Elements
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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
- 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 invention relates to a preparation method of a polyimide composite material of a fastening piece. The preparation of polyimide matrix resin comprises the processes of firstly, performing esterification reaction on ethanol and mixed aromatic dianhydrides respectively, and adding 4,4'-diaminodiphenyl ether to perform condensation polymerization after anhydride esterification; then, performing an end-capping reaction on 5-norbornene-2,3-dioctyl phthalate mono-ethyl ester to generate an oligomer, and performing soaking kneading on the oligomer and glass fibers treated by an organic silane coupling agent; and finally, performing heat treatment to prepare a polyimide presoaked material, and performing hot press molding to prepare the needed product. The prepared self-locking fastening piece has the performance that the thread carrying capacity is 11KN and the tensile fracture force is 2.9KN, and the materials comprise 1mol of the mixed aromatic dianhydrodes,1mol of the 4,4'-diaminodiphenyl ether, and 0.25-0.75 mol of 5-norbornadiene 2,3-dimethylbenzene anhydride. During esterification of the materials with ethanol, the mole ratio of anhydride to alcohol is 1:(4-10), the reaction temperature is 69-90 DEG C, and the reaction time is 2-5 hours.
Description
One, technical field
The present invention relates to the preparation method of composite polyimide material for fastening piece, more precisely a-ODPA and other dianhydride monomer are added to 4 in alcoholic solution after esterification, 4'-diaminodiphenyl oxide generation polycondensation, and with the norbornene dicarboxylic anhydride end-blocking of same esterification, then impregnated glass fiber or carbon fiber, make polyimide preimpregnation material; The preparation method of composite polyimide material for final formation fastening piece.
Two, background technology
So-called fastening piece means two or more parts or the general name of member is fastening while linking together type part used.As bolt, nut, packing ring, screw, pin, rivet etc.The prepared fastening piece of composite polyimide material prepared by the present invention refers to screwed self-locking fastening piece.As bolt, nut, screw rod and screw etc.
5-norbornylene-2, the polyimide of 3-dicarboxylic anhydride (NA) end-blocking is mainly used in matrix material, as making layer pressing plate, structure unit and high temperature resistant and insulated product.Aspect aspect aircraft and electrical equipment, for making air-distribution engines engine parts, circuit card, click slot wedge, stator and rotor insulation side plate etc.Also can be used as sizing agent.Consider physical strength, thermostability and processing and price factor, few for the report of fastening piece.
PMMI Vespel moulding compound, life-time service temperature is up to 288 ℃, and heatproof reaches 480 ℃ in short-term, has low temperature frictional coefficient and high abrasion resistance properties, degassed, the low particle of rough vacuum produces and intrinsic purity, for making screw, bolt, nut, threaded rod, packing ring etc.In automobile, machinery, processing unit, aerospace and semiconductor applications, apply.But forming process difficulty needs again through operations such as car, milling and upper screw threads, and cost is higher.
The polyimide material that provides practical self-locking fastening piece to use, needs research and development with great concentration really, could contribute novel material for high-technology field, new product.
Three, summary of the invention
The polyimide material that self-locking fastening piece is used, the material of especially small-sized bolt processing use, at present domestic still scarce this polyimide material.The present inventors, through particular study, provide product practical for user, have filled up domestic blank.Its complete skill scheme is as follows:
Fastening piece has following polymer repeating unit with composite polyimide material:
In formula, m:n=1:0.3～3, m+n=1.3～4
This composite polyimide material preparation method's processing step comprise: the preparation of polyimid-base resin: first with ethanol respectively with mix aromatic dianhydride, 5-norbornylene-2,3-dicarboxylic anhydride generation esterification; Mixing after aromatic dianhydride esterification finishes adds 4,4'-diaminodiphenyl oxide to carry out polycondensation; Then with 5-norbornylene-2,3-diformate mono ethyl ester carries out end capping and generates oligopolymer polyimid-base resin; Polyimid-base resin is mediated with glass fibre or impregnated carbon fiber that organo-silicon coupling agent was processed again; Then, thermal treatment makes polyimide preimpregnation material, carries out the hot-forming required product of producing; The self-locking fastener performance wherein making is: screw thread bearing capacity 11KN, fail in tension power 2.9kN; Ratio of components is: the mol ratio of mixing aromatic dianhydride monomer and 4,4'-diaminodiphenyl oxide is 1:0.3～3; Mix aromatic dianhydride monomer and 5-norbornadiene 2, the mol ratio of 3-dicarboxylic acid anhydride is 1:0.25～0.75; During esterification, the mol ratio of mixing aromatic dianhydride monomer and ethanol is 1:4～10,5-norbornylene-2, and the mol ratio of 3-dicarboxylic anhydride and ethanol is 1:4～10,69～90 ℃ of esterification reaction temperatures, 2～5 hours reaction times.
Mixing aromatic dianhydride described in the present invention is 2,3,3', 4'-diphenyl ether tetraformic dianhydride be selected from 3,3', 4,4'-dihydroxyphenyl propane diphenyl ether tetraformic dianhydride, 3,3', 4,4'-bibenzene tetracarboxylic dianhydride, 2,3', 4,4'-bibenzene tetracarboxylic dianhydride, 3,4,3', a kind of mixture in 4'-diphenyl ether tetraformic dianhydride or pyromellitic acid anhydride.
Mixing aromatic dianhydride described in the present invention is preferably 2,3,3', 4'-diphenyl ether tetraformic dianhydride and 3,3', 4, the mixture of 4'-dihydroxyphenyl propane diphenyl ether tetraformic dianhydride, wherein 2,3,3', 4'-diphenyl ether tetraformic dianhydride and 3,3', the mol ratio of 4,4'-dihydroxyphenyl propane diphenyl ether tetraformic dianhydride is 1:0.6～1.0; Mix aromatic dianhydride monomer and 5-norbornadiene 2, the mol ratio of 3-dicarboxylic acid anhydride is 1.6～2.0:1.5; The mol ratio of mixing aromatic dianhydride monomer and 4,4'-diaminodiphenyl oxide is 1.6～2.0:2.0.
Organo-silicon coupling agent described in the present invention is selected from a kind of in γ aminopropyltriethoxy silane, γ-glycidyl oxygen propyl trimethoxy silicane or their mixture; The heat treatment process that described thermal treatment makes polyimide preimpregnation material is via 80 ℃/3h, 160 ℃/2h, makes polyimide preimpregnation material after 230 ℃/1h.
The hot-forming condition of the polyimide preimpregnation material described in the present invention is 310～330 ℃/4MPa, and hot pressing time is with test specimen size, thickness and determining.
Glass fibre described in the present invention or carbon fiber consumption are 10 % by weight～55 % by weight of composite polyimide material weight.
If the direct compression molding bolt of polyimide preimpregnation material described in the present invention, nut, processing temperature is still 310～330 ℃/4Mpa.The screw thread bearing capacity obtaining is 11KN, and the fail in tension power of bolt is 2.9KN.
The composite polyimide material of preparing according to the present invention, there are 5-norbornylene-2,3-dicarboxylic acid anhydride (NA) end-blocking or 5-norbornylene-2, all features of the composite polyimide material of 3-diformate mono ethyl ester (NE) end-blocking, be that NA capped polyimides pre-impregnating process is simple, the stable performance of preimpregnation material, pressing Heat stability is good, life-time service temperature is 260 ℃～300 ℃, and satisfactory mechanical property goes, its veneer sheet porosity low (< 2%), and can adopt general lamination process processes.More valuable is forming process good fluidity, and curing speed is the direct mold pressing bolt of energy soon, can process stove bolt especially, and bolt tension destructive force is 2.9KN, and screw thread bearing capacity is 11KN.
Four, embodiment
In order to implement better the present invention, especially exemplified by embodiment, it is described, but embodiment limitation of the present invention anything but.
Embodiment 1
(1) preparation of single acid esters
246g(1.5mol) 5-norbornylene-2,3-dicarboxylic acid anhydride 69 ℃～90 ℃ reflux in 259g ethanol make 5-norbornylene-2 for 2 hours, 3-diformate mono ethyl ester (NE).
286g(1mol) 2,3,3', 4'-diphenyl ether tetraformic dianhydride makes 2,3,3' for 5 hours with 69～90 ℃ of back flow reaction in 256g ethanol, 4'-diphenyl ether tetraformic mono ethyl ester.
514g(1mol) 3,3', 4,4'-dihydroxyphenyl propane diphenyl ether tetraformic dianhydride makes 3,3' for 2 hours with 71 ℃～90 ℃ reflux in 463g ethanol, 4,4'-dihydroxyphenyl propane diphenyl ether tetraformic mono ethyl ester.
(2) preparation of polyimid-base resin
400g(2mol) 4,4'-diaminodiphenyl oxide is dissolved in 358g ethanol and stirs half an hour, then, add 2,3 of above-mentioned preparation, 3', 4'-diphenyl ether tetraformic mono ethyl ester and 3,3', in 4,4'-dihydroxyphenyl propane diphenyl ether tetraformic mono ethyl ester mixture, stir after 1～2 hour, with 5-norbornylene-2,3-diformate mono ethyl ester (NE), 70 ℃～83 ℃ stirring reactions 5 hours, obtains solution of polyimid-base resin.
(3) preparation of polyimide preimpregnation material
What 160g and organo-silicon coupling agent γ aminopropyltriethoxy silane were processed is glass fiber impregnated in solution of polyimid-base resin, through fully mediating, via 80 ℃/3h, 160 ℃/2h, 230 ℃/1h thermal treatment acquisition polyimide preimpregnation material.
(4) preparation of composite product
Polyimide preimpregnation material is under 310～330 ℃/4MPa, and hot-press solidifying obtains required product.
The heat-drawn wire of matrix material hot pressing part is 312 ℃, tensile strength 52.4MPa, flexural strength 118MPa.
With polyimide preimpregnation material compression molding bolt, nut, condition of molding, be directly still 310～330 ℃/4MPa, obtain self-locking fastening piece, its screw thread bearing capacity is 11KN, and bolt tension destructive force is 2.9KN.
Embodiment 2
Except 2,3,3', the consumption of 4'-diphenyl ether tetraformic dianhydride is 1mol, 3,3', 4,4'-dihydroxyphenyl propane diphenyl ether tetraformic dianhydride consumption is 0.6mol, and solution of polyimid-base resin preparation is by 5-norbornylene-2,3-diacid mono ethyl ester, 2,3,3', 4'-diphenyl ether tetraformic mono ethyl ester and 3,3', the ethanolic soln of 4,4'-dihydroxyphenyl propane tetracarboxylic acid mono ethyl ester and the ethanolic soln hybrid reaction of 4,4'-diaminodiphenyl oxide; What organo-silicon coupling agent γ aminopropyltriethoxy silane was processed is glass fiber impregnated in the solution of polyimid-base resin making, other formula is the same with embodiment 1 with operation steps, and result screw thread bearing capacity is that 10KN bolt tension destructive force is 2.5KN.
Embodiment 3
Except replacing glass fibre with carbon fiber, other formula is the same with embodiment 1 with operation steps, result screw thread bearing capacity 13KN, and bolt tension destructive force is 3.1KN.
Claims (6)
1. a preparation method for composite polyimide material for fastening piece, is characterized in that, polyimid-base resin has the structure of following polymer repeating unit:
In formula, m:n=1:0.3～3, m+n=1.3～4
This composite polyimide material preparation method's processing step comprise: the preparation of polyimid-base resin: first with ethanol respectively with mix aromatic dianhydride, 5-norbornylene-2,3-dicarboxylic anhydride generation esterification; Mixing after aromatic dianhydride esterification finishes adds 4,4'-diaminodiphenyl oxide to carry out polycondensation; Then with 5-norbornylene-2,3-diformate mono ethyl ester carries out end capping and generates oligopolymer polyimid-base resin; Polyimid-base resin is mediated with glass fibre or impregnated carbon fiber that organo-silicon coupling agent was processed again; Then, thermal treatment makes polyimide preimpregnation material, carries out the hot-forming required product of producing; The self-locking fastener performance wherein making is: screw thread bearing capacity 11KN, fail in tension power 2.9kN; Ratio of components is: the mol ratio of mixing aromatic dianhydride monomer and 4,4'-diaminodiphenyl oxide is 1:0.3～3; Mix aromatic dianhydride monomer and 5-norbornadiene 2, the mol ratio of 3-dicarboxylic acid anhydride is 1:0.25～0.75; During esterification, the mol ratio of mixing aromatic dianhydride monomer and ethanol is 1:4～10,5-norbornylene-2, and the mol ratio of 3-dicarboxylic anhydride and ethanol is 1:4～10,69～90 ℃ of esterification reaction temperatures, 2～5 hours reaction times.
2. the preparation method of composite polyimide material for a kind of fastening piece according to claim 1, is characterized in that, described mixing aromatic dianhydride is 2,3,3', 4'-diphenyl ether tetraformic dianhydride be selected from 3,3', 4,4'-dihydroxyphenyl propane diphenyl ether tetraformic dianhydride, 3,3', 4,4'-bibenzene tetracarboxylic dianhydride, 2,3', 4,4'-bibenzene tetracarboxylic dianhydride, 3,4,3', a kind of mixture in 4'-diphenyl ether tetraformic dianhydride or pyromellitic acid anhydride.
3. the preparation method of composite polyimide material for a kind of fastening piece according to claim 1 and 2, is characterized in that, described mixing aromatic dianhydride is 2,3,3', 4'-diphenyl ether tetraformic dianhydride and 3,3', the mixture of 4,4'-dihydroxyphenyl propane diphenyl ether tetraformic dianhydride, wherein 2,3,3', 4'-diphenyl ether tetraformic dianhydride and 3,3', the mol ratio of 4,4'-dihydroxyphenyl propane diphenyl ether tetraformic dianhydride is 1:0.6～1.0; Mix aromatic dianhydride monomer and 5-norbornadiene 2, the mol ratio of 3-dicarboxylic acid anhydride is 1.6～2.0:1.5; The mol ratio of mixing aromatic dianhydride monomer and 4,4'-diaminodiphenyl oxide is 1.6～2.0:2.0.
4. the preparation method of composite polyimide material for a kind of fastening piece according to claim 1, it is characterized in that, described organo-silicon coupling agent is selected from a kind of in γ aminopropyltriethoxy silane, γ-glycidyl oxygen propyl trimethoxy silicane or their mixture; The heat treatment process that described thermal treatment makes polyimide preimpregnation material is via 80 ℃/3h, 160 ℃/2h, makes polyimide preimpregnation material after 230 ℃/1h.
5. the preparation method of composite polyimide material for a kind of fastening piece according to claim 1, is characterized in that, the hot-forming condition of described polyimide preimpregnation material is 310～330 ℃/4MPa, and hot pressing time is with test specimen size, thickness and determining.
6. the preparation method of composite polyimide material for a kind of fastening piece according to claim 1, is characterized in that, described glass fibre or carbon fiber consumption are 10 % by weight～55 % by weight of composite polyimide material weight.
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| CN201310739971.3A CN103740104B (en) | 2013-12-27 | 2013-12-27 | The preparation method of securing member composite polyimide material |
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| CN201310739971.3A CN103740104B (en) | 2013-12-27 | 2013-12-27 | The preparation method of securing member composite polyimide material |
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| CN103740104A true CN103740104A (en) | 2014-04-23 |
| CN103740104B CN103740104B (en) | 2016-08-17 |
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Cited By (1)
| 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)
| 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 |
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2013
- 2013-12-27 CN CN201310739971.3A patent/CN103740104B/en active Active
Patent Citations (3)
| 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 |
Cited By (1)
| 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 |
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Address after: 200235 No. 36, Xuhui District, Shanghai, Caobao Road Patentee after: SHANGHAI RESEARCH INSTITUTE OF SYNTHETIC RESINS Co.,Ltd. Address before: 200235 No. 36, Xuhui District, Shanghai, Caobao Road Patentee before: SHANGHAI Research Institute OF SYNTHETIC RESINS |
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Effective date of registration: 20210224 Address after: No. 1251, Zhulu West Road, Xujing Town, Qingpu District, Shanghai, 201702 Patentee after: SHANGHAI PLASTICS RESEARCH INSTITUTE Co.,Ltd. Address before: 200235 No. 36, Xuhui District, Shanghai, Caobao Road Patentee before: SHANGHAI RESEARCH INSTITUTE OF SYNTHETIC RESINS Co.,Ltd. |