CN1123602C - Refractory antiwear polyimide as sealing material and its preparing process and application - Google Patents
Refractory antiwear polyimide as sealing material and its preparing process and application Download PDFInfo
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- CN1123602C CN1123602C CN00103461A CN00103461A CN1123602C CN 1123602 C CN1123602 C CN 1123602C CN 00103461 A CN00103461 A CN 00103461A CN 00103461 A CN00103461 A CN 00103461A CN 1123602 C CN1123602 C CN 1123602C
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- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/62—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyesters
- D01F6/64—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyesters from polycarbonates
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Abstract
The present invention relates to a preparation method and an application of a composite sealing polyimide material with high temperature resistance, abrasive resistance and a thermosetting property. The composite sealing material is prepared by compounding an PMR(pimaricin)-type thermosetting polyimide substrate resin, reinforcing materials (quartz chopped fibers, glass chopped fibers or Kevlar chopped fibers and a mixture thereof) and functional additive agents (graphite, molybdenum disulfide, polytetrafluoroethylene, copper powder or ceramic powder). The preparation method comprises two stages, namely the preparation of moulding powder and the pressure forging of the composite sealing material. The present invention has the advantages of excellent high temperature resistance, mechanical property, abrasive resistance, self-lubricating property, corrosion resistance, rust resistance and simple moulding process; the composite sealing material has a stable mechanical property in a temperature range of-100 to-450 DEG C and is a sealing material with good performance.
Description
The present invention relates to a kind of preparation method and application thereof of PMR type Thermocurable polyimide sealing material of abrasion performance.
In industrial production and daily life, sealing has great importance.Advanced seal means not only can improve running period, reduction consumption, save energy, the minimizing of equipment to be polluted, eliminates public hazards, and is the important assurance of safety in production.The performance of sealing member depends mainly on selected sealing material.
It is matrix that United States Patent (USP) (U.S.Pat.5695197) discloses with the tetrafluoroethylene, and small amount of thermal plastic polyimide and carbon fiber have the method for favorable elasticity wear ring for the additive manufacturing.But its shortcoming is a poor heat resistance, and the life-time service temperature generally is no more than 250 ℃, and the poor mechanical property of sealing member, and abrasion resistance is undesirable.In addition, there are shortcomings such as cold flow in the tetrafluoroethylene product.European patent (Eu.Patent 0626423A1) discloses thermoplastic polyimide and graphite and wollastonite additive have been pressed into blank earlier under high pressure (290MPa), high temperature sintering (400 ℃) is made blank then, after mechanical workout prepares the method for low-expansion coefficient sealing member.But the moulding of the patented product needs very high pressure (689MPa), and sealing member is easy to generate shortcomings such as crack or hole.
The present invention has overcome polytetrafluoroethylene (PTFE) base sealing material resistance toheat and poor mechanical property, thermoplastic polyimide sealing member complex forming technology, condition harshness, is easy to generate the shortcoming of crackle and provides that a kind of moulding process is simple, high temperature resistant, the Thermocurable polyimide sealing material of abrasion performance.The life-time service temperature of sealing material is 320-370 ℃, and the short-term use temperature can reach 400-450 ℃.
Thermocurable polyimide sealing material of the present invention contains component as shown in table 1 and weight proportion:
The composition and the proportioning of table 1 Thermocurable polyimide sealing material
| Component | Weight percentage |
| Thermoset polyimide resin staple fibre strongthener functional particles filler | 30-98 1-35 1-35 |
Thermoset polyimide resin of the present invention means that PMR type thermoset polyimide resin is prepared by following compounds and derivative thereof.
(1) organic solvent
(2) aromatic diamine
(3) aromatic diacid diester
(4) end-capping reagent
Organic solvent of the present invention means methyl alcohol, ethanol, Virahol, N-Methyl pyrrolidone, N, N
1-N,N-DIMETHYLACETAMIDE, N, N '-dimethyl formamide and mixed system thereof.
Aromatic series tetracarboxylic dianhydride of the present invention means organic compound that has following chemical structure and composition thereof:
Organic aromatic diamine of the present invention means organic compound that has following chemical structure and composition thereof:
R
2:-CH
2-,-O-,-SO
2-,-CO-, end-capping reagent of the present invention means organic compound that has following chemical structure and composition thereof:
PMR polyimide type resin of the present invention is characterized in that its manufacture method comprises following step: aromatic diacid diester and end-capping reagent list acid monoester are reacted the corresponding polyimide resin solution of generation with aromatic diamine in organic solvent.
Strongthener of the present invention means that length is 1-50mm, and diameter is that chopped carbon fiber, glass fibre, the Kev of 0.5-50um reined in fiber.
Functional particles additive of the present invention is polytetrafluoroethylene powder, Graphite Powder 99, molybdenum disulphide powder, copper powder, whisker or the ceramic of granularity at 15-75 μ m.
High temperature resistant, self-lubricating of the present invention, antiwear polyimide matrix material is characterized in that its preparation method comprises following step:
1) substrate resin solution and strongthener are mixed with certain proportioning, make it abundant infiltration.So
After, remove most of solvent gradually, obtain the moving shape material of heavy-gravity semi-fluid.
2) the above-mentioned dynamic material of semi-fluid of heat treated in the air cycle convection oven makes it to be dried to
Solid.The continuation heating makes it to take place series of chemical and obtains the molding powder.The baking of molding powder
The change procedure of roasting temperature and storing time is as shown in table 2.
The preparation condition of the molding powder of table 2, composite polyimide material
Temperature (℃) the constant temperature treatment time (hr)
70-120 1-4
100-180 1-4
180-240 1-4
The molding powder that adopts aforesaid method to make has suitable process flowability, and its melt flow index (MFI) [press the GB3682-83 method and measure, the 5.00kg that wherein loads, mouthful mould internal diameter =1.18mm] is in 1.0-4.0g/ minute scope.
3) the molding powder is added in the mould, generate thermoset through a series of heating and cure under pressure reaction
Composite polyimide material.Mold temperature scope: 250-400 ℃, the forming pressure scope:
0.5-10MPa
Polyimide seal part of the present invention can the pattern tool the precision control tolerance of dimension that obtains requiring, directly installation use need not mechanical secondary processing.Polyimide seal part outward appearance is highly polished, and interior porosity is low, and technology stability is good.Table 3 is listed the resistance toheat of composite seal.
The typical resistance toheat of table 3 matrix material
Table 4 is that the condition of molding of the art of this patent and European patent (Eur.Patent 0626423A1) technology compares.
| Initial decomposition temperature, ℃ | 540-555 |
| 5% thermal weight loss temperature, ℃ | 530-540 |
| 10% thermal weight loss temperature, ℃ | 550-570 |
| Second-order transition temperature (Tg), ℃ | 360-400 |
| Ppm/ ℃ of thermal expansivity (CTE) | 40-55 |
| Constant temperature weightlessness, % (371 ℃/200 hours) | 4.0-6.0 |
The condition of molding of table 4 Thermocurable polyimide sealing material and thermoplastic polyimide sealing material relatively
| Material type | Mold temperature, ℃ | Forming pressure, MPa | The sealing member moulding process |
| The Thermocurable polyimide thermoplastic polyimide | 320 or 370 400 | 3-10 690 | Once shaped XianCheng parison material, machining again |
Thermocurable polyimide sealing material of the present invention can be widely used in the sealing component of the refractory antiwear in the new and high technology industries such as fields such as commercial market such as electric machinery, mining machinery, textile manufacturing machine, chemical machinery, medical machinery and automotive industry and space flight and aviation.The sealing part has the unexistent over-all properties of other sealing material in-250 to 450 ℃ temperature environment, it is simple that high temperature resistant, corrosion-resistant, self-lubricating, abrasion performance, high low temperature exert oneself to learn excellent performance, size Heat stability is good, not fusion, non-corrosive, moulding process, the advantage that has engineering plastics, alloy in lightweight and pottery concurrently is in one, high/low temperature sealing, high/low means of press seals, high speed seal and inflammable, explosive, poisonous, strong corrosive medium, the grains of sand and suspension particle in seal aspect be with a wide range of applications.
Example
Example 1. is with 400 part 4, and reflux esterification in ethanol becomes corresponding aroma family two acid diesters and end-capping reagent list acid monoester to 4 '-hexafluoro sec.-propyl-two Tetra hydro Phthalic anhydrides with 33 parts of norbornylene acid anhydrides; In organic solvent and 108 part 1, the reaction of 4-Ursol D generates corresponding substrate resin solution with the aromatic diacid diester of above-mentioned preparation and end-capping reagent list acid monoester; Get 850 parts of substrate resin solutions and mix, make it abundant infiltration with the mixture of 55 parts of short glass fiber+15 part graphite+10 parts of copper powders.The above-mentioned mixture of heat treated makes solvent evaporates in the air cycle convection oven.Continuing to be heated to 200 ℃ of insulations made it to take place series of chemical in 2 hours and obtains the molding powder.120g molding powder is added in the mould, then mould is put into and be preheated to 200 ℃ of press and heat, pressurization 1-10MPa continues to be heated to 320-325 ℃ of pressurize 2 hours in the time of 280-290 ℃, be warming up to 350-360 ℃ of pressurize 2 hours then, at last 370-375 ℃ of pressurize 2 hours.Relief pressure when being cooled to below 200 ℃ naturally takes out composite material moulded sealing member.553 ℃ of the initial heat decomposition temperatures of gained matrix material, 521 ℃ of 5% thermal weight loss temperature, second-order transition temperature: 385 ℃; Flexural strength: 100-120MPa; Tensile strength: 60-80MPa; Static friction coefficient: 0.23; Lubricating status frictional coefficient: 0.06-0.07.
Example 2. is with 400 part 4, and reflux esterification in methyl alcohol becomes corresponding aroma family two acid diesters and end-capping reagent list acid monoester to 4 '-hexafluoro sec.-propyl-two Tetra hydro Phthalic anhydrides with 33 parts of norbornylene acid anhydrides; The aromatic diacid diester and the end-capping reagent list acid monoester of above-mentioned preparation are generated corresponding substrate resin solutions with 108 parts of aromatic diamines reactions in organic solvent; 125 parts of mean lengths silica fiber that is 1mm and 25 parts of molybdenum disulphide powders are added have in the glass there-necked flask of whipping appts and protection of inert gas device and water distilling apparatus, add 700 parts of solid contents and be 50% PMR resin solution, vigorous stirring 20 minutes.Then, remove most of solvent gradually, obtain the moving shape material of heavy-gravity semi-fluid.The above-mentioned dynamic material of semi-fluid of heat treated makes it to be dried to solid in the air cycle convection oven.Continuing to be heated to 200 ℃ of insulations made it to take place series of chemical in 2 hours and obtains the molding powder.100g molding powder is added in the mould, then mould is put into and be preheated to 200 ℃ of press and heat, pressurization 1-10MPa continues to be heated to 320-325 ℃ of pressurize 2 hours in the time of 280-290 ℃, be warming up to 350-360 ℃ of pressurize 2 hours then, at last 370-375 ℃ of pressurize 2 hours.Relief pressure when being cooled to below 200 ℃ naturally takes out composite material moulded sealing member.
Example 3. is with 400 part 4, and reflux esterification in ethanol becomes corresponding aroma family two acid diesters and end-capping reagent list acid monoester to 4 '-hexafluoro sec.-propyl-two Tetra hydro Phthalic anhydrides with 33 parts of norbornylene acid anhydrides; In organic solvent and 108 part 1, the reaction of 4-Ursol D generates corresponding substrate resin solution with the aromatic diacid diester of above-mentioned preparation and end-capping reagent list acid monoester; The glass fibre that to get 100 parts of mean lengths be 50mm; 30 parts of Graphite Powder 99s and 20 parts of whiskers add and have in the glass there-necked flask of whipping appts and protection of inert gas device and water distilling apparatus; adding 750 parts of solid contents is the 50%PMR resin solution, vigorous stirring 20 minutes.Then, remove most of solvent gradually, obtain the moving shape material of heavy-gravity semi-fluid.The above-mentioned dynamic material of semi-fluid of heat treated makes it to be dried to solid in the air cycle convection oven.Continuing to be heated to 200 ℃ of insulations made it to take place series of chemical in 2 hours and obtains the molding powder.105g molding powder is added in the mould, then mould is put into and be preheated to 200 ℃ of press and heat, pressurization 1-10 M Pa continues to be heated to 320-325 ℃ of pressurize 2 hours in the time of 280-290 ℃, be warming up to 350-360 ℃ of pressurize 2 hours then, at last 370-375 ℃ of pressurize 2 hours.Relief pressure when being cooled to below 200 ℃ naturally takes out composite material moulded sealing member.
Example 4. is with 64 part 3,3,4, and reflux esterification in ethanol becomes corresponding aroma family two acid diesters and end-capping reagent list acid monoester to the 4-benzophenone tetracarboxylic dianhydride with 33 parts of norbornylene acid anhydrides; In organic solvent and 60 part 1, the reaction of 4-diaminodiphenylmethane generates corresponding substrate resin solution with the aromatic diacid diester of above-mentioned preparation and end-capping reagent list acid monoester; With the carbon fiber that 100 parts of mean lengths are 25mm, 30 parts of Graphite Powder 99s and 20 parts of copper powders add and have in the glass there-necked flask of whipping appts and protection of inert gas device and water distilling apparatus, and adding 700 parts of solid contents is the 50%PMR resin solution, vigorous stirring 20 minutes.Then, remove most of solvent gradually, obtain the moving shape material of heavy-gravity semi-fluid.The above-mentioned dynamic material of semi-fluid of heat treated makes it to be dried to solid in the air cycle convection oven.Continuing to be heated to 200 ℃ of insulations made it to take place series of chemical in 2 hours and obtains the molding powder.105g molding powder is added in the mould, then mould is put into and be preheated to 200 ℃ of press and heat, pressurization 1-10MPa continues to be heated to 320-325 ℃ of pressurize 2 hours in the time of 280-290 ℃.Relief pressure when being cooled to below 200 ℃ naturally takes out composite material moulded sealing member.
Example 5. is with 64 part 3,3,4, and reflux esterification in ethanol becomes corresponding aroma family two acid diesters and end-capping reagent list acid monoester to the 4-benzophenone tetracarboxylic dianhydride with 33 parts of norbornylene acid anhydrides; In organic solvent and 60 part 1, the reaction of 4-diaminodiphenylmethane generates corresponding substrate resin solution with the aromatic diacid diester of above-mentioned preparation and end-capping reagent list acid monoester; The Kev that 100 parts of mean lengths are 5mm is reined in fiber; 30 parts of molybdenum disulphide powders and 20 parts of copper powders add and have in the glass there-necked flask of whipping appts and protection of inert gas device and water distilling apparatus; adding 350 parts of solid contents is the 50%PMR resin solution, vigorous stirring 20 minutes.Then, remove most of solvent gradually, obtain the moving shape material of heavy-gravity semi-fluid.The above-mentioned dynamic material of semi-fluid of heat treated makes it to be dried to solid in the air cycle convection oven.Continuing to be heated to 200 ℃ of insulations made it to take place series of chemical in 2 hours and obtains the molding powder.10.5g molding powder is added in the mould, then mould is put into and be preheated to 200 ℃ of press and heat, pressurization 1-10MPa continues to be heated to 320-325 ℃ of pressurize 2 hours in the time of 280-290 ℃.Relief pressure when being cooled to below 200 ℃ naturally takes out composite material moulded sealing member.
Example 6. is with 64 part 3,3,4, and reflux esterification in ethanol becomes corresponding aroma family two acid diesters and end-capping reagent list acid monoester to the 4-benzophenone tetracarboxylic dianhydride with 33 parts of norbornylene acid anhydrides; In organic solvent and 60 part 1, the reaction of 4-diaminodiphenylmethane generates corresponding substrate resin solution with the aromatic diacid diester of above-mentioned preparation and end-capping reagent list acid monoester; With 120 parts of mean lengths whisker that is 5mm; 20 part of 15 μ m tetrafluoroethylene and 10 parts of copper powders add and have in the glass there-necked flask of whipping appts and protection of inert gas device and water distilling apparatus; adding 350 parts of solid contents is the 50%PMR resin solution, vigorous stirring 20 minutes.Then, remove most of solvent gradually, obtain the moving shape material of heavy-gravity semi-fluid.The above-mentioned dynamic material of semi-fluid of heat treated makes it to be dried to solid in the air cycle convection oven.Continuing to be heated to 200 ℃ of insulations made it to take place series of chemical in 2 hours and obtains the molding powder.10.5g molding powder is added in the mould, then mould is put into and be preheated to 200 ℃ of press and heat, pressurization 1-10MPa continues to be heated to 320-325 ℃ of pressurize 2 hours in the time of 280-290 ℃.Relief pressure when being cooled to below 200 ℃ naturally takes out composite material moulded sealing member.
Example 7. is with 62 part 3,3,4, and reflux esterification in ethanol becomes corresponding aroma family two acid diesters and end-capping reagent list acid monoester to 4-two methyl-phenoxide tetracarboxylic dianhydrides with 33 parts of norbornylene acid anhydrides; In organic solvent and 60 part 1, the reaction of 4-diaminodiphenylmethane generates corresponding substrate resin solution with the aromatic diacid diester of above-mentioned preparation and end-capping reagent list acid monoester; With 100 parts of mean lengths chopped carbon fiber that is 5mm; 30 part of 15 μ m Graphite Powder 99 and 20 part of 25 μ m copper powder add and have in the glass there-necked flask of whipping appts and protection of inert gas device and water distilling apparatus; adding 350 parts of solid contents is the 40%PMR resin solution, vigorous stirring 20 minutes.Then, remove most of solvent gradually, obtain the moving shape material of heavy-gravity semi-fluid.The above-mentioned dynamic material of semi-fluid of heat treated makes it to be dried to solid in the air cycle convection oven.Continuing to be heated to 200 ℃ of insulations made it to take place series of chemical in 2 hours and obtains the molding powder.10.5g molding powder is added in the mould, then mould is put into and be preheated to 200 ℃ of press and heat, pressurization 1-10MPa continues to be heated to 320-325 ℃ of pressurize 2 hours in the time of 280-290 ℃.Relief pressure when being cooled to below 200 ℃ naturally takes out composite material moulded sealing member.
Example 8. is with 62 part 3,3,4, and reflux esterification in ethanol becomes corresponding aroma family two acid diesters and end-capping reagent list acid monoester to 4-two methyl-phenoxide tetracarboxylic dianhydrides with 33 parts of norbornylene acid anhydrides; In organic solvent and 60 part 1, the reaction of 4-diaminodiphenylmethane generates corresponding substrate resin solution with the aromatic diacid diester of above-mentioned preparation and end-capping reagent list acid monoester; With 75 parts of mean lengths glass fibre that is 5mm; the Kev that 35 parts of mean lengths are 6-8mm is reined in fiber and 35 parts of molybdenum disulphide powders and is added and have in the glass there-necked flask of whipping appts and protection of inert gas device and water distilling apparatus; adding 350 parts of solid contents is the 40%PMR resin solution, vigorous stirring 20 minutes.Then, remove most of solvent gradually, obtain the moving shape material of heavy-gravity semi-fluid.The above-mentioned dynamic material of semi-fluid of heat treated makes it to be dried to solid in the air cycle convection oven.Continuing to be heated to 200 ℃ of insulations made it to take place series of chemical in 2 hours and obtains the molding powder.105g molding powder is added in the mould, then mould is put into and be preheated to 200 ℃ of press and heat, pressurization 1-10MPa continues to be heated to 320-325 ℃ of pressurize 2 hours in the time of 280-290 ℃.Relief pressure when being cooled to below 200 ℃ naturally takes out composite material moulded sealing member.
Example 9-is with 410 part 4, and the reflux esterification in ethanol of 4 '-hexafluoro sec.-propyl-two Tetra hydro Phthalic anhydrides becomes corresponding aroma family two acid diesters and end-capping reagent list acid monoester; In organic solvent and 98 part 1,4-Ursol D and 38 parts of p-aminophenyl ethylene reactions generate corresponding substrate resin solution with the aromatic diacid diester of above-mentioned preparation; The glass fibre that to get 100 parts of mean lengths be 5mm; 30 parts of Graphite Powder 99s and 20 part of 75 μ m whisker add and have in the glass there-necked flask of whipping appts and protection of inert gas device and water distilling apparatus; adding 750 parts of solid contents is the 50%PMR resin solution, vigorous stirring 20 minutes.Then, remove most of solvent gradually, obtain the moving shape material of heavy-gravity semi-fluid.The above-mentioned dynamic material of semi-fluid of heat treated makes it to be dried to solid in the air cycle convection oven.Continuing to be heated to 200 ℃ of insulations made it to take place series of chemical in 2 hours and obtains the molding powder.105g molding powder is added in the mould, then mould is put into and be preheated to 200 ℃ of press and heat, pressurization 1-10MPa continues to be heated to 320-325 ℃ of pressurize 2 hours in the time of 280-290 ℃, be warming up to 350-360 ℃ of pressurize 2 hours then, at last 370-375 ℃ of pressurize 2 hours.Relief pressure when being cooled to below 200 ℃ naturally takes out composite material moulded sealing member.
Claims (4)
1, a kind of refractory antiwear Thermocurable polyimide sealing material is characterized in that described sealing material contains following component and content:
The component parts by weight
(1) thermoset polyimide resin 30-98
(2) staple fibre strongthener 1-35
(3) functional additive 1-35
Described functional additive is graphite, molybdenumdisulphide, tetrafluoroethylene, copper powder or the ceramics powder of granularity at 15-75 μ m.
2, the Thermocurable polyimide sealing material of a kind of refractory antiwear according to claim 1, it is characterized in that the staple fibre that is adopted is chopped carbon fiber, short glass fiber, weak point is cut silica fiber, Kev reins in fiber or/and whisker, the length of fiber is between 1-50mm.
3, the preparation method who expects according to the Thermocurable polyimide sealing of the described a kind of refractory antiwear of claim 1 is characterized in that its preparation method comprises following step:
(1) be that 50% polyimide resin solution and chopped carbon fiber, glass fibre or Kev are towed with concentration
Dimension and tetrafluoroethylene thereof, graphite, molybdenumdisulphide, copper powder, whisker or ceramics powder are pressed 30-98:
The proportioning of 1-35: 1-35 is mixed, and makes it abundant infiltration, gets thickness semi-fluid shape material,
(2) with the moving shape material oven dry of the above-mentioned thickness semi-fluid that obtains, obtain solid, with solid at 140-230 ℃
Handle after 2-4 hour, pulverize, obtain melt flow index 1-4g/ minute molding powder,
(3) the above-mentioned molding powder that obtains is added in the mould, be heated to 250-400 ℃, 0.5-10MPa's
Pressure curing down obtained composite seal in 2-5 hour.
4, the purposes of a kind of refractory antiwear Thermocurable polyimide sealing material according to claim 1, but it is characterized in that once shaped makes the matrix material seal structural part of desired shape.
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| CN00103461A CN1123602C (en) | 2000-03-13 | 2000-03-13 | Refractory antiwear polyimide as sealing material and its preparing process and application |
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| CN00103461A CN1123602C (en) | 2000-03-13 | 2000-03-13 | Refractory antiwear polyimide as sealing material and its preparing process and application |
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| CN1123602C true CN1123602C (en) | 2003-10-08 |
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| DE3204491A1 (en) * | 1981-02-11 | 1982-09-02 | Valeo, 75848 Paris | CLUTCH RELEASE |
| JPS62132960A (en) * | 1985-12-06 | 1987-06-16 | Ube Ind Ltd | Polyimide resin formed body |
| US5180761A (en) * | 1991-05-24 | 1993-01-19 | National Science Council | Polymer based self-lubrication composite |
| JPH05112723A (en) * | 1991-10-22 | 1993-05-07 | Sutaaraito Kogyo Kk | Conductive composition for sliding member |
| CN1080647A (en) * | 1992-06-22 | 1994-01-12 | 蓬莱市大雪实业总公司 | High temperature resistant self-lubricating composite and manufacture method |
| JPH06240233A (en) * | 1993-02-18 | 1994-08-30 | Toshiba Tungaloy Co Ltd | Wet friction material |
| CN1186827A (en) * | 1996-12-24 | 1998-07-08 | 中国科学院兰州化学物理研究所 | Polyimide self lubricating composite material |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1313361A (en) | 2001-09-19 |
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