US3629103A - Plastic antifriction material - Google Patents
Plastic antifriction material Download PDFInfo
- Publication number
- US3629103A US3629103A US835785A US3629103DA US3629103A US 3629103 A US3629103 A US 3629103A US 835785 A US835785 A US 835785A US 3629103D A US3629103D A US 3629103DA US 3629103 A US3629103 A US 3629103A
- Authority
- US
- United States
- Prior art keywords
- antifriction material
- percent
- prepared
- weight
- aromatic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000003831 antifriction material Substances 0.000 title claims abstract description 33
- 239000004033 plastic Substances 0.000 title abstract description 9
- 229920003023 plastic Polymers 0.000 title abstract description 9
- 229920001721 polyimide Polymers 0.000 claims abstract description 22
- 229920001230 polyarylate Polymers 0.000 claims abstract description 21
- 239000000314 lubricant Substances 0.000 claims abstract description 13
- 239000007787 solid Substances 0.000 claims abstract description 13
- 239000004760 aramid Substances 0.000 claims abstract description 9
- 229920003235 aromatic polyamide Polymers 0.000 claims abstract description 9
- 239000000945 filler Substances 0.000 claims abstract description 9
- 239000009719 polyimide resin Substances 0.000 claims abstract description 7
- 239000004642 Polyimide Substances 0.000 claims description 15
- 238000006068 polycondensation reaction Methods 0.000 claims description 9
- 239000004952 Polyamide Substances 0.000 claims description 8
- -1 aromatic dicarboxylic acid chlorides Chemical class 0.000 claims description 8
- 229920002647 polyamide Polymers 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 claims description 6
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 5
- 229930185605 Bisphenol Natural products 0.000 claims description 5
- 229940018564 m-phenylenediamine Drugs 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 claims description 5
- 229910052982 molybdenum disulfide Inorganic materials 0.000 claims description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 4
- 150000004984 aromatic diamines Chemical class 0.000 claims description 4
- 150000001805 chlorine compounds Chemical class 0.000 claims description 4
- 229910002804 graphite Inorganic materials 0.000 claims description 4
- 239000010439 graphite Substances 0.000 claims description 4
- 239000012255 powdered metal Substances 0.000 claims description 4
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 claims description 4
- LGROVJABHMQYIR-UHFFFAOYSA-N 1,2-diphenyl-9h-fluorene-3,4-diol Chemical compound C=1C=CC=CC=1C1=C(O)C(O)=C2C3=CC=CC=C3CC2=C1C1=CC=CC=C1 LGROVJABHMQYIR-UHFFFAOYSA-N 0.000 claims description 3
- PLYHMRQAXIKUIV-UHFFFAOYSA-N 3,3-bis(4-aminophenyl)-2-benzofuran-1-one Chemical compound C1=CC(N)=CC=C1C1(C=2C=CC(N)=CC=2)C2=CC=CC=C2C(=O)O1 PLYHMRQAXIKUIV-UHFFFAOYSA-N 0.000 claims description 3
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052709 silver Inorganic materials 0.000 claims description 3
- 239000004332 silver Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 claims description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 238000000465 moulding Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- ZHDTXTDHBRADLM-UHFFFAOYSA-N hydron;2,3,4,5-tetrahydropyridin-6-amine;chloride Chemical compound Cl.NC1=NCCCC1 ZHDTXTDHBRADLM-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M7/00—Solid or semi-solid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single solid or semi-solid substances
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/04—Elements
- C10M2201/041—Carbon; Graphite; Carbon black
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/04—Elements
- C10M2201/041—Carbon; Graphite; Carbon black
- C10M2201/042—Carbon; Graphite; Carbon black halogenated, i.e. graphite fluoride
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/04—Elements
- C10M2201/05—Metals; Alloys
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/06—Metal compounds
- C10M2201/065—Sulfides; Selenides; Tellurides
- C10M2201/066—Molybdenum sulfide
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/102—Polyesters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/024—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/042—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds between the nitrogen-containing monomer and an aldehyde or ketone
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/043—Mannich bases
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/044—Polyamides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/045—Polyureas; Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/02—Bearings
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/08—Solids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy
Definitions
- Plastic antifriction materials derived from polyimide In order to prepare an aljltifriction "i i noted for its plastics filled with solid lubricants, e.g., graphite or molybenhanced thermal and electrical conduiuvlty metal P denum disulfide are known e.g., powdered copper or silver, are incorporated into the blend of the aforesaid components at the mixing step.
- solid lubricants e.g., graphite or molybenhanced thermal and electrical conduiuvlty metal
- P denum disulfide e.g., powdered copper or silver
- blies such as bearing cages, sliding bearing bushings, and geared transmission components.
- this known antifric- Th 1 tion material exhibits a marked increase of its friction coeffie Y tam mouldmg composition winch consists of a cient with the increase of the working temperatures up to finely dlvlded hpmogeneous powder Subjected to ugh-tem- 70l20f C., whiehprecludes the employment of the material perature mouldmg' under the aforesaid conditions, despite its good mechanical above PmFedure ylelds an annfncuonmatenal exhlbn' characteristics mg high mechanical strength, good workability, a stable coef- It an object of the present mvenuon to ehmmate the ficlent of friction over awide temperature range, and superior aforementioned disadvantage. wear reslstanc-e' For a better understanding of the present invention, given hereinbelow are the following examples of preparing the antifriction material.
- the resultant polyamidoacid is precipitated mides, exhibit superior performance characteristics due to with a benzene-acetone mixture taken in a five-fold excess and their less pronounced authohesion properties.
- the incorporation of rigid-chain polyarylates or aromatic polyamido acid thus obtained is then polycyclized in vacuo (1 polyamides into a polyimide resin-based antifriction material mm. Hg) at a temperature of 100 C. for 2 hours, at 200 C. exerts a stabilizing effect on the coefficient of friction over a for 3 hours, and at 300 C. for 1.5 hours. wide temperature range.
- Polycyclization yields a polyimide having the following It is expedient to employ an antifriction material of the folstructural formula 0 0 II II 0. N O r C O u lowing composition, percent by weight: polyimide, 4-78; filler I (solid lubricants), 2-95, and polyarylates or aromatic polya-
- polyimide, 4-78 polyimide, 4-78; filler I (solid lubricants), 2-95, and polyarylates or aromatic polya-
- the Polylmlde l5 tl'llulated oblaln a homogeneous mides, 1-20. powder.
- solid lubricants 2-75
- polyarylates or aromatic polyamides 1-20
- metal powders 20-40.
- the antifriction material is prepared as follows.
- H H V C C() C -O- be of the following composition, percent by weight: polyimide
- the polyimide obtained in the form of a fused mass is The polyarylate having the aforespecified structure is thoroughly ground to prepare a homogeneous powder which prepared from terephthaloyl chloride and phenolphthalein by is then mixed in a vibrating mill with powdered polyarylate or the high-temperature polycondensation technique.
- the aromatic polyamide and powdered filler solid lubricant, e.g., process is conducted at a temperature of 220 C. for a period molybdenum disulfide or graphite).
- the resultant polyarylate is dissolved in chloroform to obprocessed. tain a 5 percent solution and thereafter precipitated with a
- the polyarylates employed as an antifriction material comfive-fold excess of methyl alcohol, filtered off and dried at a ponent are prepared from aromatic dicarboxylic acid tempe ature of 12 C- for 6 h urs.
- the components are mixed in a vibrating mill to give a equilibrium high-temperature polycondensation method.
- the moulding composition, which is thereafter moulded at a tempolyarylates thus obtained are precipitated with an excess of perature of 390-4 10 C. and a specific pressure of 1,000 to solvent, filtered off and dried to constant weight. 1,200 kg./cm.”.
- EXAMPLE 2 A Polymide of the general formula derived from diphenyl oxide 3,3',4,4'-tetracarboxylic acid dianhydride and m-phenylene diamine, and a polyarylate of the general formula V M I derived from terephthaloyl dichloride and dihydroxydiphenylfluorene are prepared as disclosed in example 1.
- the moulding composition thus prepared is subjected to moulding at a temperature of 490500 C. and a specific pressure of 1.000 to 1,200 kg./cm.
- EXAMPLE 3 Fifty grams of powdered a polyimide prepared as disclosed in example 1 is mixed in a vibrating mill with 420 g. of graphite powder and 20 g. of polymetaphenylene isophthalamide ofthe structural formula Intensity oflinear wear 0.9x 10' Coefficicnt of friction 0.1 Maximum working temperature. C. 250
- EXAMPLE 4 37.5 g. of powdered polyimide prepared as disclosed in example 2 is mixed in a vibrating mill for a period of 2 minutes with 450 g. of graphite powder and 12.5 g. of polyamide havl0 ing the structural formula II 0 h 20 the polyamide being synthesized from anilinephthalein and isophthalic acid by the method disclosed in example 3.
- the moulding powder thus obtained is moulded at a temperature of 490-500 C. and under a specific pressure of 1,000 to 1,200 kg./cm.
- EXAMPLE 5 37.5 g. of powdered polyimide and 12.5 g. of polyarylate prepared as disclosed in example 1, 325 g. of molybdenum disulftde powder (particle size, l-2y.), and 125 g. of copper powder are blended in a vibrating mill for a period of 2 minutes.
- the moulding composition thus obtained is moulded at a temperature of 3904l0 C. and under specific pressure of 1,000 to 1.200 kg./cm.
- EXAMPLE 6 37.5 g. of powdered polyimide prepared as disclosed in example 1. 12.5 g. of polyamide prepared by the procedure of example 3, 325 g. of molybdenum disulfide powder (particle size. 1-2u), and 125 g. of silver powder are mixed in a vibrating mill for a period of 2 minutes.
- the moulding composition thus obtained is subjected to compression moulding at a temperature of 3904l0 C. and under specific pressure of 1,000 to 1,200 kg./cm.
- An antifriction material having a stable coefficient of friction over a wide temperature range comprising 1. 4 to 78 percent by weight of one or more aromatic polyimide resins prepared by polycondensation of an aromatic diamine with an aromatic tetracarboxylic acid dianhydride to yield a polyamido carboxylic acid which after being subjected to polycyclization gives a polyimide,
- rigid-chain polymers selected from the group consisting of a) polyarylates prepared by polycondensation of aromatic dicarboxylic acid chlorides and bisphenols and (b) aromatic polyamides prepared by polycondensation of aromatic diamines and aromatic dicarboxylic acids or their chlorides.
- An antifriction material as in claim 1 which further comprises a powdered metal filler.
- An antifriction material as in claim 2 which comprises 4 to 78 percent of polyimide resin, 2 to 78 percent by weight of solid lubricants, 20 to 40 percent by weight of powdered metal filler, and l to 20 percent by weight of the polyarylate or aro- 6 matic polyamide polymer.
- polyimide is prepared from diphenyl oxide 3,3, 4, 4-tetracarbox' ylic dianhydride and a diamine selected from the group consisting of 4,4-diaminodiphenyl ether and m-phenylenediamine.
- An antifriction material as in claim 1 wherein the polyarylate is prepared from terephthaloyl chloride and a bisphenol selected from the group consisting of phenolphthalein and dihydroxydiphenyl fluorene.
- An antifriction material as in claim 1 wherein the polyamide is prepared from isophthaloyl dichloride and an amine selected from the group consisting of m-phenylenediamine and anilinephthalein.
- An antifriction material as in claim 1 wherein the solid lubricant is selected from the group consisting of molybdenum disulfide and graphite.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Lubricants (AREA)
Abstract
A plastic antifriction material containing a polyimide resin, powdered solid lubricants as fillers, and also polyarylates or aromatic polyamides.
Description
United States Patent [72] Inventors Vasily Vladimirovich Korshak ulitsa Gubkina, 4, kv. 81; Irina Alexandrovna Gribova, ulitsa Vavilova, l2, kv. 31; Alexandr Petrovich Krasnov, prospekt Kalinina, 31, kv. 28; Alla Nikolaevna Chumaevskaya, Leninsky prospekt, 101, korpus 163, kv. 86; Olga Svyatoslavovna Natsarenus, ulitsa Grimau, 13, korpus 2, kv. l5; Svellana Vasilievna Vinogradova, Belyaevo-Bogorodskoe, Kvartal 48-a, korpus 6a, kv. 63; Yakov Semenovich Vygodsky, Leninsky prospekt, 101, korpus 135, kv. 38; Vyacheslav Alexandrovich Pankratov, ulitsa Usievicha, 25, kv. 135; Grigory Lvovich Slonimsky, ulitsa Chkalova, l/4, kv. 16, all 01' Moscow, U.S.S.R.
[21] Appl. No. 835,785
[22] Filed June 23, 1969 [45] Patented Dec. 21, 1971 [54] PLASTIC ANTlFRlCTlON MATERIAL 8 Claims, No Drawings [52] U.S.Cl 252/12 [51] lm. Cl C10m 7/34 [50] Field of Search 252/12, 12.2, 12.4, 12.6
[56] References Cited UNITED STATES PATENTS 2,698,966 1/1955 Stott et al. 252/12 3,122,505 2/1964 Rulon-Miller et al 252/12 3,287,288 11/1966 Reiling 252/12 Primary Examiner--Daniel E. Wyman Assistant Examiner-l. Vaughn Attorney-Waters, Roditi, Schwartz & Nissen ABSTRACT: A plastic antifriction material containing a polyimide resin, powdered solid lubricants as fillers, and also polyarylates or aromatic polyam ides.
PLASTIC ANTIFRlCTlO N MATERIAL V 4 To preparethe aromatic polyamides used as an antifriction This invention relates to plastic antifriction materials inmaterlal f i afomanc dmmlnes and aromatic dwarf tended for the fabrication of elements of dry-friction assemboxyhc acld chlorides m a etrahydmfuran'wateSoda medlum are subjected to low-temperature olycondensation, fol- 5 lowed by filtering off and drying the resultant polymers.
Plastic antifriction materials derived from polyimide In order to prepare an aljltifriction "i i noted for its plastics filled with solid lubricants, e.g., graphite or molybenhanced thermal and electrical conduiuvlty metal P denum disulfide are known e.g., powdered copper or silver, are incorporated into the blend of the aforesaid components at the mixing step.
blies, such as bearing cages, sliding bearing bushings, and geared transmission components.
When used in dry friction assemblies, this known antifric- Th 1 tion material exhibits a marked increase of its friction coeffie Y tam mouldmg composition winch consists of a cient with the increase of the working temperatures up to finely dlvlded hpmogeneous powder Subjected to ugh-tem- 70l20f C., whiehprecludes the employment of the material perature mouldmg' under the aforesaid conditions, despite its good mechanical above PmFedure ylelds an annfncuonmatenal exhlbn' characteristics mg high mechanical strength, good workability, a stable coef- It an object of the present mvenuon to ehmmate the ficlent of friction over awide temperature range, and superior aforementioned disadvantage. wear reslstanc-e' For a better understanding of the present invention, given hereinbelow are the following examples of preparing the antifriction material.
It is a further and more specific object of the present invention to provide an antifriction material noted for its stable coefficient of friction over'a wide temperature range.
' This object is accomplished by the provision of a plastic an- EXAMPLE 1 tlfriction material derived from a polyimide resin filled with powdered solid lubricants and also containing, according to Dianhydride f diphenyl oxide-3.3. .4-tetracarboxylic the invention, polyarylates or aromatic polyamides. acid and diaminodiphenyl ether taken in a molar ratio of 1:1 Under dry friction conditions when polymer molecules are are subjected to polycondensation in dimethylformamide at a subjected to both thermal effects and mechanical cracking, temperature of 10-25 C. for a period of 4 hours, with conrigid-chain polymers, such as polyarylates or aromatic polyatinuous stirring. The resultant polyamidoacid is precipitated mides, exhibit superior performance characteristics due to with a benzene-acetone mixture taken in a five-fold excess and their less pronounced authohesion properties. dried in a vacuum cabinet at 80 C. for 2 hours. The dry The incorporation of rigid-chain polyarylates or aromatic polyamido acid thus obtained is then polycyclized in vacuo (1 polyamides into a polyimide resin-based antifriction material mm. Hg) at a temperature of 100 C. for 2 hours, at 200 C. exerts a stabilizing effect on the coefficient of friction over a for 3 hours, and at 300 C. for 1.5 hours. wide temperature range. Polycyclization yields a polyimide having the following It is expedient to employ an antifriction material of the folstructural formula 0 0 II II 0. N O r C O u lowing composition, percent by weight: polyimide, 4-78; filler I (solid lubricants), 2-95, and polyarylates or aromatic polya- The Polylmlde l5 tl'llulated oblaln a homogeneous mides, 1-20. powder.
in order to enhance the thermal and electrical conductivity 8- of the Powdered Polylmlde, 450 of Powdered of the present antifriction material, to improve its moldability molybdenum dlsulfide (parlklle Size and 8- of and also to raise its hardness and wear resistance, it is good p l f l' p y y ofthe following Structural formula practice to additionally incorporate thereinto metal powders as fillers.
-78; solid lubricants, 2-75; polyarylates or aromatic polyamides, 1-20, and metal powders, 20-40.
The antifriction material, according to the present invention, is prepared as follows.
Polycondensation of an aromatic diamine with an aromatic O tetracarboxylic acid dianhydride yields a polyamido carboxyli id, hi h, on b i ubj t d t olycyclization gives a are mixed in a vibrating mill for 2 minutes until a homogeneo v 0 7 1n the latter case, the antifriction material should preferably H H V C C() C -O- be of the following composition, percent by weight: polyimide,
polyimide. ous mass is obtained.
The polyimide obtained in the form of a fused mass is The polyarylate having the aforespecified structure is thoroughly ground to prepare a homogeneous powder which prepared from terephthaloyl chloride and phenolphthalein by is then mixed in a vibrating mill with powdered polyarylate or the high-temperature polycondensation technique. The aromatic polyamide and powdered filler (solid lubricant, e.g., process is conducted at a temperature of 220 C. for a period molybdenum disulfide or graphite). The polyarylate o amof 12 hours and comprises stirring, in a stream of argon, a mix matic polyamide used as a component of the antifriction ture of equimolar amounts of the starting compounds dismaterial should have a softening or melting point that lies solved in Sovol(chlorinated biphenyl). close to the temperature at. which the polyimide is being The resultant polyarylate is dissolved in chloroform to obprocessed. tain a 5 percent solution and thereafter precipitated with a The polyarylates employed as an antifriction material comfive-fold excess of methyl alcohol, filtered off and dried at a ponent are prepared from aromatic dicarboxylic acid tempe ature of 12 C- for 6 h urs. chlorides and bisphenols in a high-boiling solvent by the The components are mixed in a vibrating mill to give a equilibrium high-temperature polycondensation method. The moulding composition, which is thereafter moulded at a tempolyarylates thus obtained are precipitated with an excess of perature of 390-4 10 C. and a specific pressure of 1,000 to solvent, filtered off and dried to constant weight. 1,200 kg./cm.".
The antifriction material prepared as disclosed hereinbefore exhibits the following physical and mechanical characteristics:
Brincll hardness. kgjmm. 20 Impact strength. kg./cm./cm. 3 intensity of linear wear IXIO Coefficient of friction 0.12 Maximum working temperature. C. 240
EXAMPLE 2 A Polymide of the general formula derived from diphenyl oxide 3,3',4,4'-tetracarboxylic acid dianhydride and m-phenylene diamine, and a polyarylate of the general formula V M I derived from terephthaloyl dichloride and dihydroxydiphenylfluorene are prepared as disclosed in example 1.
37.5 g. of the powdered polyimide, 12.5 g. of the powdered polyarylate and 450 g. of powdered molybdenum disulfide (particle size, 1-2,u) are mixed in a vibrating mill for a period of 2 minutes to obtain a homogeneous mass.
The moulding composition thus prepared is subjected to moulding at a temperature of 490500 C. and a specific pressure of 1.000 to 1,200 kg./cm.
The antifriction material exhibits the following physical and mechanical characteristics:
Brinell hardness, kg/mm. 21 Impact strength. kg.cm./cm.' 2 Intensity of linear wear 1.3Xl()" Coefficient of linear wear 0.12 Maximum working temperature. C. 260
EXAMPLE 3 Fifty grams of powdered a polyimide prepared as disclosed in example 1 is mixed in a vibrating mill with 420 g. of graphite powder and 20 g. of polymetaphenylene isophthalamide ofthe structural formula Intensity oflinear wear 0.9x 10' Coefficicnt of friction 0.1 Maximum working temperature. C. 250
EXAMPLE 4 37.5 g. of powdered polyimide prepared as disclosed in example 2 is mixed in a vibrating mill for a period of 2 minutes with 450 g. of graphite powder and 12.5 g. of polyamide havl0 ing the structural formula II 0 h 20 the polyamide being synthesized from anilinephthalein and isophthalic acid by the method disclosed in example 3.
The moulding powder thus obtained is moulded at a temperature of 490-500 C. and under a specific pressure of 1,000 to 1,200 kg./cm.
The antifriction material exhibits the following physical and mechanical characteristics:
Intensity oflincar wear 0.9Xl0 Coefficicnt of friction 0.1 Maximum working temperature. C. 270
EXAMPLE 5 37.5 g. of powdered polyimide and 12.5 g. of polyarylate prepared as disclosed in example 1, 325 g. of molybdenum disulftde powder (particle size, l-2y.), and 125 g. of copper powder are blended in a vibrating mill for a period of 2 minutes.
The moulding composition thus obtained is moulded at a temperature of 3904l0 C. and under specific pressure of 1,000 to 1.200 kg./cm.
The antifriction material exhibits the following physical and mechanical characteristics:
Brinell hardness. kgjmm. 24 Impact strength. kg.cm./em. 2.5 Coefficient of friction 0.1 N Maximum working temperature, C. 250
EXAMPLE 6 37.5 g. of powdered polyimide prepared as disclosed in example 1. 12.5 g. of polyamide prepared by the procedure of example 3, 325 g. of molybdenum disulfide powder (particle size. 1-2u), and 125 g. of silver powder are mixed in a vibrating mill for a period of 2 minutes.
The moulding composition thus obtained is subjected to compression moulding at a temperature of 3904l0 C. and under specific pressure of 1,000 to 1,200 kg./cm.
The antifriction material exhibits the following physical and mechanical characteristics:
Brinell hardness. kgJmm. Z2 Intensity of linear wcar (1.7X10 Maximum working temperature. "C. 250
Although the present invention has been described with reference to the preferred embodiment thereof, it will be readily understood by those skilled in the art that various changes and modifications can be practised without departing from the spirit and scope of the invention as disclosed in the description and appended claims.
We claim:
1. An antifriction material having a stable coefficient of friction over a wide temperature range comprising 1. 4 to 78 percent by weight of one or more aromatic polyimide resins prepared by polycondensation of an aromatic diamine with an aromatic tetracarboxylic acid dianhydride to yield a polyamido carboxylic acid which after being subjected to polycyclization gives a polyimide,
2. 2 to 75 percent by weight of one or more solid inorganic lubricants, and
3. l to percent by weight of one or more rigid-chain polymers selected from the group consisting of a) polyarylates prepared by polycondensation of aromatic dicarboxylic acid chlorides and bisphenols and (b) aromatic polyamides prepared by polycondensation of aromatic diamines and aromatic dicarboxylic acids or their chlorides.
2. An antifriction material as in claim 1 which further comprises a powdered metal filler.
3. An antifriction material as in claim 2 which comprises 4 to 78 percent of polyimide resin, 2 to 78 percent by weight of solid lubricants, 20 to 40 percent by weight of powdered metal filler, and l to 20 percent by weight of the polyarylate or aro- 6 matic polyamide polymer.
4. An antifriction material as in claim 1 wherein the polyimide is prepared from diphenyl oxide 3,3, 4, 4-tetracarbox' ylic dianhydride and a diamine selected from the group consisting of 4,4-diaminodiphenyl ether and m-phenylenediamine.
5. An antifriction material as in claim 1 wherein the polyarylate is prepared from terephthaloyl chloride and a bisphenol selected from the group consisting of phenolphthalein and dihydroxydiphenyl fluorene.
6. An antifriction material as in claim 1 wherein the polyamide is prepared from isophthaloyl dichloride and an amine selected from the group consisting of m-phenylenediamine and anilinephthalein.
7. An antifriction material as in claim 1 wherein the solid lubricant is selected from the group consisting of molybdenum disulfide and graphite.
8. An antifriction material as in claim 2 wherein the metal is copper or silver.
Claims (9)
- 2. 2 to 75 percent by weight of one or more solid inorganic lubricants, and
- 2. An antifriction material as in claim 1 which further comprises a powdered metal filler.
- 3. 1 to 20 percent by weight of one or more rigid-chain polymers selected from the group consisting of (a) polyarylates prepared by polycondensation of aromatic dicarboxylic acid chlorides and bisphenols and (b) aromatic polyamides prepared by polycondensation of aromatic diamines and aromatic dicarboxylic acids or their chlorides.
- 3. An antifriction material as in claim 2 which comprises 4 to 78 percent of polyimide resin, 2 to 78 percent by weight of solid lubricants, 20 to 40 percent by weight of powdered metal filler, and 1 to 20 percent by weight of the polyarylate or aromatic polyamide polymer.
- 4. An antifriction material as in claim 1 wherein the polyimide is prepared from diphenyl oxide 3,3'', 4, 4'' -tetracarboxylic dianhydride and a diamine selected from the group consisting of 4,4''-diaminodiphenyl ether and m-phenylenediamine.
- 5. An antifriction material as in claim 1 wherein the polyarylate is prepared from terephthaloyl chloride and a bisphenol selected from the group consisting of phenolphthalein and dihydroxydiphenyl fluorene.
- 6. An antifriction material as in claim 1 wherein the polyamide is prepared from isophthaloyl dichloride and an amine selected from the group consisting of m-phenylenediamine and anilinephthalein.
- 7. An antifriction material as in claim 1 wherein the solid lubricant is selected from the group consisting of molybdenum disulfide and graphite.
- 8. An antifriction material as in claim 2 wherein the metal is copper or silver.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83578569A | 1969-06-23 | 1969-06-23 | |
| GB33616/69A GB1244427A (en) | 1969-06-23 | 1969-07-03 | Antifriction material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3629103A true US3629103A (en) | 1971-12-21 |
Family
ID=26261943
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US835785A Expired - Lifetime US3629103A (en) | 1969-06-23 | 1969-06-23 | Plastic antifriction material |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3629103A (en) |
| GB (1) | GB1244427A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3928673A (en) * | 1973-08-16 | 1975-12-23 | Ball Brothers Res Corp | Release and lubricating composition for glass molds and method and apparatus utilizing such composition |
| US4075111A (en) * | 1976-04-19 | 1978-02-21 | Hughes Aircraft Company | Heavy metal chalcogenide-polyimide lubricative composites |
| US4076634A (en) * | 1974-10-28 | 1978-02-28 | Vasily Vladimirovich Korshak | Composition for antifriction material |
| US4371445A (en) * | 1979-03-14 | 1983-02-01 | Heinz Faigle Kg | Arrangement in pairs of plastic sliding on plastic in tribologic systems |
| FR2537990A1 (en) * | 1982-12-17 | 1984-06-22 | Kobe Steel Ltd | Film of lubricant and process for preventing chafing of sliding metal surfaces |
| US4532054A (en) * | 1982-12-28 | 1985-07-30 | General Electric Company | Polyetherimide bearing compositions |
| WO1998007785A1 (en) * | 1996-08-19 | 1998-02-26 | E.I. Du Pont De Nemours And Company | Polyimide polymeric blends |
| US10711526B2 (en) | 2017-02-01 | 2020-07-14 | Baker Hughes, A Ge Company, Llc | Methods for forming or servicing a wellbore, and methods of coating surfaces of tools |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0122305A1 (en) * | 1983-04-15 | 1984-10-24 | General Electric Company | Polyetherimide-polyamide blends |
| RU2232786C2 (en) * | 2002-05-08 | 2004-07-20 | ОАО "Заволжский моторный завод" | Composite material and a method of its production for realization of a required heat-transfer factor |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2698966A (en) * | 1951-09-27 | 1955-01-11 | Polymer Corp | Process for producing shaped articles from mixtures of polyamides |
| US3122505A (en) * | 1961-04-11 | 1964-02-25 | Dixon Corp | Bearing composition |
| US3287288A (en) * | 1964-09-21 | 1966-11-22 | Duriron Co | Low friction composition containing a resinous binder and degraded polytetrafluoroethylene particles |
-
1969
- 1969-06-23 US US835785A patent/US3629103A/en not_active Expired - Lifetime
- 1969-07-03 GB GB33616/69A patent/GB1244427A/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2698966A (en) * | 1951-09-27 | 1955-01-11 | Polymer Corp | Process for producing shaped articles from mixtures of polyamides |
| US3122505A (en) * | 1961-04-11 | 1964-02-25 | Dixon Corp | Bearing composition |
| US3287288A (en) * | 1964-09-21 | 1966-11-22 | Duriron Co | Low friction composition containing a resinous binder and degraded polytetrafluoroethylene particles |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3928673A (en) * | 1973-08-16 | 1975-12-23 | Ball Brothers Res Corp | Release and lubricating composition for glass molds and method and apparatus utilizing such composition |
| US4076634A (en) * | 1974-10-28 | 1978-02-28 | Vasily Vladimirovich Korshak | Composition for antifriction material |
| US4075111A (en) * | 1976-04-19 | 1978-02-21 | Hughes Aircraft Company | Heavy metal chalcogenide-polyimide lubricative composites |
| US4371445A (en) * | 1979-03-14 | 1983-02-01 | Heinz Faigle Kg | Arrangement in pairs of plastic sliding on plastic in tribologic systems |
| FR2537990A1 (en) * | 1982-12-17 | 1984-06-22 | Kobe Steel Ltd | Film of lubricant and process for preventing chafing of sliding metal surfaces |
| US4532054A (en) * | 1982-12-28 | 1985-07-30 | General Electric Company | Polyetherimide bearing compositions |
| WO1998007785A1 (en) * | 1996-08-19 | 1998-02-26 | E.I. Du Pont De Nemours And Company | Polyimide polymeric blends |
| CN1098310C (en) * | 1996-08-19 | 2003-01-08 | 纳幕尔杜邦公司 | Polyimide polymeric blends |
| US10711526B2 (en) | 2017-02-01 | 2020-07-14 | Baker Hughes, A Ge Company, Llc | Methods for forming or servicing a wellbore, and methods of coating surfaces of tools |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1244427A (en) | 1971-09-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3629103A (en) | Plastic antifriction material | |
| US3850820A (en) | Antifriction structural material produced from composition comprising carborane-containing polymer binders and solid lubricant | |
| US7758781B2 (en) | Blends of high temperature resins suitable for fabrication using powdered metal or compression molding techniques | |
| US3652409A (en) | Bearing compositions | |
| US5416154A (en) | Bearing material | |
| JPS61126169A (en) | Polyamide resin composition | |
| US3453208A (en) | Low friction bearings with improved wear properties | |
| KR20150040930A (en) | Coating composition containing polyamide-imide resin | |
| US3808130A (en) | Self-lubricating bearings and other machine elements and a process for their manufacture | |
| US3649601A (en) | Aromatic polyimides containing perfluoroalkylene groups | |
| US3513134A (en) | Polyamide-imide enamel containing (1) dicyandiamide or (2) dicyandiamide and triphenyl phosphite | |
| JPH09508161A (en) | Polyimide composition having improved properties | |
| CA1148926A (en) | Lubricating composition | |
| US5179153A (en) | Wear resistant polyimide composition | |
| US3730893A (en) | Solid lubricants and method | |
| US3530068A (en) | Plastic antifriction materials | |
| EP0626423A1 (en) | Low thermal-expansion polyimide compositions | |
| US3773787A (en) | Imido polyphenyl oxides | |
| US4064097A (en) | Antifriction polymer material | |
| SU379592A1 (en) | METHOD OF OBTAINING ANTIFRICTION MATERIAL | |
| Kim et al. | Copolyamides derived from brassylic acid | |
| US3821112A (en) | Heat-resistant antifriction polymeric material | |
| JPS6236458A (en) | Polyamide composition and production thereof | |
| JPH0225938B2 (en) | ||
| JPS61225247A (en) | Abrasion resistant poly(aryl ether ketone)/polyimide mixture |