EP1812187B1 - Powder metal composition comprising secondary amides as lubricant and/or binder - Google Patents
Powder metal composition comprising secondary amides as lubricant and/or binder Download PDFInfo
- Publication number
- EP1812187B1 EP1812187B1 EP05783351A EP05783351A EP1812187B1 EP 1812187 B1 EP1812187 B1 EP 1812187B1 EP 05783351 A EP05783351 A EP 05783351A EP 05783351 A EP05783351 A EP 05783351A EP 1812187 B1 EP1812187 B1 EP 1812187B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition according
- lubricant
- amide
- iron
- powder
- 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.)
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- 239000000843 powder Substances 0.000 title claims abstract description 72
- 239000000203 mixture Substances 0.000 title claims abstract description 69
- 239000000314 lubricant Substances 0.000 title claims abstract description 66
- 150000003334 secondary amides Chemical class 0.000 title claims abstract description 38
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 35
- 239000002184 metal Substances 0.000 title claims abstract description 35
- 239000011230 binding agent Substances 0.000 title claims abstract description 29
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 66
- 229910052742 iron Inorganic materials 0.000 claims abstract description 31
- 150000003140 primary amides Chemical class 0.000 claims description 21
- 239000002245 particle Substances 0.000 claims description 17
- VMRGZRVLZQSNHC-ZCXUNETKSA-N n-[(z)-octadec-9-enyl]hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(=O)NCCCCCCCC\C=C/CCCCCCCC VMRGZRVLZQSNHC-ZCXUNETKSA-N 0.000 claims description 16
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 claims description 15
- -1 pentadecenyl Chemical group 0.000 claims description 14
- 150000001408 amides Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 238000002844 melting Methods 0.000 claims description 10
- 230000008018 melting Effects 0.000 claims description 10
- 238000005245 sintering Methods 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- DJWFNQUDPJTSAD-UHFFFAOYSA-N n-octadecyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)CCCCCCCCCCCCCCCCC DJWFNQUDPJTSAD-UHFFFAOYSA-N 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- UAUDZVJPLUQNMU-UHFFFAOYSA-N Erucasaeureamid Natural products CCCCCCCCC=CCCCCCCCCCCCC(N)=O UAUDZVJPLUQNMU-UHFFFAOYSA-N 0.000 claims description 7
- 229940037312 stearamide Drugs 0.000 claims description 7
- FUSNPOOETKRESL-ZPHPHTNESA-N (z)-n-octadecyldocos-13-enamide Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)CCCCCCCCCCC\C=C/CCCCCCCC FUSNPOOETKRESL-ZPHPHTNESA-N 0.000 claims description 6
- 229910002804 graphite Inorganic materials 0.000 claims description 6
- 239000010439 graphite Substances 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 230000001050 lubricating effect Effects 0.000 claims description 6
- VZGOTNLOZGRSJA-ZZEZOPTASA-N (z)-n-octadecyloctadec-9-enamide Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)CCCCCCC\C=C/CCCCCCCC VZGOTNLOZGRSJA-ZZEZOPTASA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000005275 alloying Methods 0.000 claims description 5
- UAUDZVJPLUQNMU-KTKRTIGZSA-N erucamide Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(N)=O UAUDZVJPLUQNMU-KTKRTIGZSA-N 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- PECBPCUKEFYARY-ZPHPHTNESA-N n-[(z)-octadec-9-enyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCCCCCCC\C=C/CCCCCCCC PECBPCUKEFYARY-ZPHPHTNESA-N 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- ORAWFNKFUWGRJG-UHFFFAOYSA-N Docosanamide Chemical compound CCCCCCCCCCCCCCCCCCCCCC(N)=O ORAWFNKFUWGRJG-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- OOCSVLHOTKHEFZ-UHFFFAOYSA-N icosanamide Chemical compound CCCCCCCCCCCCCCCCCCCC(N)=O OOCSVLHOTKHEFZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 229910052804 chromium Inorganic materials 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 229910052750 molybdenum Inorganic materials 0.000 claims description 3
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 claims description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 229910052721 tungsten Inorganic materials 0.000 claims description 3
- 229910052720 vanadium Inorganic materials 0.000 claims description 3
- GCAONVVVMAVFDE-CLFAGFIQSA-N (z)-n-[(z)-octadec-9-enyl]octadec-9-enamide Chemical compound CCCCCCCC\C=C/CCCCCCCCNC(=O)CCCCCCC\C=C/CCCCCCCC GCAONVVVMAVFDE-CLFAGFIQSA-N 0.000 claims description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000009792 diffusion process Methods 0.000 claims description 2
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 claims description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000755 henicosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229940116335 lauramide Drugs 0.000 claims description 2
- ILRSCQWREDREME-UHFFFAOYSA-N lauric acid amide propyl betaine Natural products CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 claims description 2
- 125000002463 lignoceryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- FLZZYGJEWGCCDH-UHFFFAOYSA-N n-tetracosyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCNC(=O)CCCCCCCCCCCCCCCCC FLZZYGJEWGCCDH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 claims description 2
- FATBGEAMYMYZAF-UHFFFAOYSA-N oleicacidamide-heptaglycolether Natural products CCCCCCCCC=CCCCCCCCC(N)=O FATBGEAMYMYZAF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 125000002469 tricosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000005040 tridecenyl group Chemical group C(=CCCCCCCCCCCC)* 0.000 claims description 2
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 claims description 2
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- HSEMFIZWXHQJAE-UHFFFAOYSA-N hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(N)=O HSEMFIZWXHQJAE-UHFFFAOYSA-N 0.000 claims 2
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- 229930195729 fatty acid Natural products 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 claims 1
- 229910052748 manganese Inorganic materials 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- RKISUIUJZGSLEV-UHFFFAOYSA-N n-[2-(octadecanoylamino)ethyl]octadecanamide Chemical group CCCCCCCCCCCCCCCCCC(=O)NCCNC(=O)CCCCCCCCCCCCCCCCC RKISUIUJZGSLEV-UHFFFAOYSA-N 0.000 description 22
- 238000005461 lubrication Methods 0.000 description 9
- 238000005056 compaction Methods 0.000 description 8
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 5
- 229940057977 zinc stearate Drugs 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000006057 Non-nutritive feed additive Substances 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 2
- 229910052580 B4C Inorganic materials 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910001315 Tool steel Inorganic materials 0.000 description 1
- AFCIMSXHQSIHQW-UHFFFAOYSA-N [O].[P] Chemical compound [O].[P] AFCIMSXHQSIHQW-UHFFFAOYSA-N 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- OYLGJCQECKOTOL-UHFFFAOYSA-L barium fluoride Chemical compound [F-].[F-].[Ba+2] OYLGJCQECKOTOL-UHFFFAOYSA-L 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 229910052839 forsterite Inorganic materials 0.000 description 1
- OFFQPEBWIQOAIP-UHFFFAOYSA-N hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(N)=O.CCCCCCCCCCCCCCCC(N)=O OFFQPEBWIQOAIP-UHFFFAOYSA-N 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229920013821 hydroxy alkyl cellulose Polymers 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- HGPXWXLYXNVULB-UHFFFAOYSA-M lithium stearate Chemical compound [Li+].CCCCCCCCCCCCCCCCCC([O-])=O HGPXWXLYXNVULB-UHFFFAOYSA-M 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000320 mechanical mixture Substances 0.000 description 1
- 150000001247 metal acetylides Chemical class 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 238000005204 segregation Methods 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- CADICXFYUNYKGD-UHFFFAOYSA-N sulfanylidenemanganese Chemical compound [Mn]=S CADICXFYUNYKGD-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
Images
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B22—CASTING; POWDER METALLURGY
- B22F—WORKING METALLIC POWDER; MANUFACTURE OF ARTICLES FROM METALLIC POWDER; MAKING METALLIC POWDER; APPARATUS OR DEVICES SPECIALLY ADAPTED FOR METALLIC POWDER
- B22F1/00—Metallic powder; Treatment of metallic powder, e.g. to facilitate working or to improve properties
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B22—CASTING; POWDER METALLURGY
- B22F—WORKING METALLIC POWDER; MANUFACTURE OF ARTICLES FROM METALLIC POWDER; MAKING METALLIC POWDER; APPARATUS OR DEVICES SPECIALLY ADAPTED FOR METALLIC POWDER
- B22F1/00—Metallic powder; Treatment of metallic powder, e.g. to facilitate working or to improve properties
- B22F1/10—Metallic powder containing lubricating or binding agents; Metallic powder containing organic material
-
- C—CHEMISTRY; METALLURGY
- C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
- C22C—ALLOYS
- C22C33/00—Making ferrous alloys
- C22C33/02—Making ferrous alloys by powder metallurgy
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B22—CASTING; POWDER METALLURGY
- B22F—WORKING METALLIC POWDER; MANUFACTURE OF ARTICLES FROM METALLIC POWDER; MAKING METALLIC POWDER; APPARATUS OR DEVICES SPECIALLY ADAPTED FOR METALLIC POWDER
- B22F3/00—Manufacture of workpieces or articles from metallic powder characterised by the manner of compacting or sintering; Apparatus specially adapted therefor ; Presses and furnaces
- B22F3/02—Compacting only
- B22F2003/023—Lubricant mixed with the metal powder
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B22—CASTING; POWDER METALLURGY
- B22F—WORKING METALLIC POWDER; MANUFACTURE OF ARTICLES FROM METALLIC POWDER; MAKING METALLIC POWDER; APPARATUS OR DEVICES SPECIALLY ADAPTED FOR METALLIC POWDER
- B22F2998/00—Supplementary information concerning processes or compositions relating to powder metallurgy
Definitions
- the present invention concerns a powder metal composition. Specifically the invention concerns a powder metal composition including a lubricant and/or binder comprising at least one secondary amide. The invention further concerns a method of producing a green body, a method of producing a bonded iron-based powder composition and use of the lubricant and/or binder.
- Metal powders are used in industry for the manufacture of metal products by compacting the metal powder in a die under high pressures, ejecting the compact from the die and optionally sintering the product.
- a lubricant is comprised in the powder in order to provide the necessary lubrication action between powder particles during compaction and between the die and the compact during ejection from the die.
- Lubrication achieved by a lubricant included in the metal powder is referred to as internal lubrication in contrast to external lubrication, which is achieved by applying a lubricant to the walls of the die, wherein the powder is compacted.
- Insufficient lubrication during ejection results in excessive friction between the compact and the die resulting in high ejection energies and damage of die surfaces and product surfaces.
- Internal lubrication is achieved by using special lubricants. Normally these lubricants are admixed with the iron or iron-based powder in the form of a powder. Some lubricants may also be used for binding additives, such as e.g. alloying elements, to the iron or iron-based particles. In these cases the lubricants thus work as binding agents and reduce or eliminate segregation of the additives during shipping and handling.
- Commonly used lubricants for PM applications are metal soaps, such as lithium and zinc stearate.
- a disadvantage with this type of lubricant is that oxides of the metals in the lubricant contaminate the inside of the sintering furnace as a result of release of metals from the lubricant during sintering, another problem is that stains may be formed on the component after sintering.
- Another commonly used lubricant is ethylene bis stearamide (EBS). Stains may also be formed on the component after sintering when using this lubricant, but to a lesser extent compared with using e.g. zinc stearate.
- EBS ethylene bis stearamide
- Stains may also be formed on the component after sintering when using this lubricant, but to a lesser extent compared with using e.g. zinc stearate.
- An object of the present invention is to provide a new powder metal composition comprising a lubricant and/or binder that reduces or eliminates the problems with high ejection forces and stained surfaces of the sintered parts.
- Further objects of the invention are to provide a method of producing compacted products and sintered or heat treated parts, a method of producing a bonded powder metal composition and use of the lubricant and/or binder.
- the powder metal composition defined in claim 1 comprising an iron based powder and a lubricant and/or binder comprising at least one secondary amide.
- the invention further concerns a method of producing a green body by subjecting the above mentioned composition to compaction.
- the method of producing a bonded powder metal composition comprises: mixing an iron-based powder with at least one secondary amide and heating the mixture to a temperature above the melting point of the at least one secondary amide.
- the invention concerns the use of the at least one secondary amide as a lubricating and/or binding agent for iron-based powders, and its use for die wall lubrication.
- the lubricant and/or binder in the powder metal composition according to the invention is at least one secondary amide that may be defined by the general formula: R 1 -NH-CO-R 2 , wherein the R 1 - and R 2 -groups, which may be the same or different, are straight or branched, saturated or unsaturated aliphatic hydrocarbon groups.
- R 1 and R 2 independently include 10 to 24 carbon atoms.
- R 1 and R 2 are selected from the group consisting of alkyl and alkenyl.
- the alkyl groups may be chosen from decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, heneicosyl, docosyl, tricosyl, tetracosyl.
- the alkenyl groups may be chosen from decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl, heneicosenyl, docosenyl, tricosenyl, tetracosenyl.
- the amount of secondary amides may constitute 0.05-2.0 % by weight of the powder metal composition, preferably 0.05-1.0% by weight.
- One embodiment of the invention concerns a powder metal composition
- a powder metal composition comprising a lubricant and/or binder further comprising at least one primary amide in addition to the at least one secondary amide.
- the at least one primary amide is preferably a saturated or unsaturated fatty acid amide having 12-24, preferably 14-22 C-atoms and most preferably 16-22 C-atoms.
- Especially preferred primary amides are stearic acid amide (stearamide), behenic acid amide (behenamide), eurcic acid amide (erucamide), palmitic acid amide (palmitamide) and arachidic acid amide (arachidamide).
- the primary and secondary amides according to the invention are either commercially obtainable or may be produced from commercially obtainable material by the use of processes well known in the art.
- the amount of primary and secondary amides may constitute a total of 0.05-2.0 % by weight of the powder metal composition, preferably 0.05-1.0% by weight.
- the amount of the at least one primary amide may be 0.05-1.0% by weight and the amount of the at least one secondary amide may be 0.05-1.0% by weight for the embodiment of the invention comprising both types of amides.
- the lubricant and/or binder may be added to the powder metal composition in the form of solid particles of each amide.
- the average particle size may vary, but is preferably less than 150 ⁇ m.
- the lubricant and/or binder may be added to the powder metal composition as a molten and subsequently solidified particulate mixture of the amides. This may be accomplished by mixing the amides in a predetermined ratio, the mixture is then melted, cooled and subsequently milled to a lubricant powder.
- the at least one secondary amide according to the invention may be used as a binder for obtaining a bonded mixture, wherein optional alloying elements and the at least one secondary amide are bonded to the iron-based powder. This may be achieved by mixing an iron-based powder with at least one secondary amide according to the invention, and heating the mixture to a temperature above the melting point of the at least one secondary amide. At least one primary amide may further be mixed into the above mentioned mixture and the heating temperature may then be lower than the melting point of the primary amide.
- the powder metal composition according to the invention may, if so desired, contain other lubricants, such as zinc stearate, lithium stearate, EBS etc.
- bonding systems such as alkydes, cellulose ester resins, hydroxyalkyl cellulose resins having 1-4 carbon atoms in the alkyl group, or thermoplastic phenolic resins.
- iron-based powder encompasses powder made up of pure iron, iron powder that has been pre-alloyed with other elements improving the strength, the hardening properties, the electromagnetic properties or other desirable properties of the end products and particles of iron mixed with particles of such alloying elements (diffusion annealed mixture or purely mechanical mixture).
- the alloying elements are copper, molybdenum, chromium, manganese, phosphorous, carbon in the form of graphite, nickel, silicon, boron, vanadium, titanium, aluminium, cobalt and tungsten, which are used either separately or in combination, e.g. in the form of compounds (Fe 3 P and FeMo).
- the iron based powders may be used for the preparation of soft magnetic parts and may, for this application, be electrically insulated. Electrical insulation of the powder particles may be made of an inorganic material. Especially suitable are the type of insulation disclosed in the US 6348265 , which concerns particles of a base powder consisting of essentially pure iron having an insulating oxygen- and phosphorus-containing barrier. Insulated powder particles are available as Somaloy TM 500 and 550 from Hoganas AB, Sweden.
- the powder metal composition according to the invention may contain one or more additives selected from the group consisting of processing aids and hard phases.
- the processing aids used in the powder metal composition may consist of talc, forsterite, manganese sulphide, sulphur, molybdenum disulphide, boron nitride, tellurium, selenium, barium difluoride and calcium difluoride, which are used either separately or in combination.
- the hard phases used in the powder metal composition may consist of carbides of tungsten, vanadium, molybdenum, chromium, Al 2 O 3 , B 4 C and various ceramic materials.
- the invention further concerns a method of producing a green body comprising: compacting the powder metal composition according to the invention to a compacted body, wherein the composition comprises an iron based powder and a lubricant and/or binder comprising at least one secondary amide having the general formula: R 1 -NH-CO-R2, wherein R 1 and R 2 are the same or different, straight or branched, saturated or unsaturated aliphatic hydrocarbon groups.
- the compacted body may be sintered or heat-treated.
- the iron-based powder, the lubricant and/or binder and optional additives may be mixed to a substantially homogeneous powder composition before the compaction step.
- the powder metal composition and/or the die may be preheated before the compaction.
- the invention further concerns the use of at least one secondary amide, defined as above, as a lubricating and/or binding agent for iron or iron based powders.
- a further embodiment of the invention concerns the use of at least one secondary amide, defined as above, as a die wall lubricant.
- Figure 1 shows stain formation of components after sintering due to the use of different lubricants.
- This example demonstrates the lubrication properties of different secondary amides and different combinations of secondary and primary amides, which are added as a powder in iron-based powder mixes.
- Base powder ASC 100.29 (available from Hoganas AB, Sweden) was mixed with 0.5% by weight of graphite (uf-4 from Kropfmuhl) and 0.8% by weight of lubricants, according to Table 3 and 4, in a Lödige mixer for 2 minutes.
- Ethylene bisstearamide (EBS, available as Licowax TM from Clariant, Germany) was used as a reference.
- the lubricants had a particle size less than 150 ⁇ m.
- Compositions comprising both a secondary and a primary amide contained 50% of each amide (0.8% by weight of the total composition).
- the base powder ASC 100.29 was mixed with 2% by weight of Copper (-100 ⁇ m), 0.8% by weight graphite and 0.8% by weight of lubricants (a) EBS or b) oleyl palmitamide) in a Lödige mixer for 2 minutes.
- the lubricants had a particle size less than 150 ⁇ m.
- cylindrical components with a diameter of 64 mm and a height of 32 mm were compacted to a green density of 7.1 g/cm 3 at ambient temperature.
- the weight of one cylinder was 700 g.
- the components were sintered in an atmosphere containing 90/10 N 2 /H 2 at 1120°C for 15 minutes.
- This example demonstrates the lubrication properties of different combinations of secondary and primary amides, which have been melted together, cooled and milled before being mixed with iron-based powder mixes.
- the lubricant combinations were made according to following method: The mixed lubricants, 50% primary and 50% secondary amide, were melted together at 80-110°C and then cooled. Then the materials were milled to a mean particle size of below 150 ⁇ m.
- the base powder ASC100.29 was mixed with 0.5 % by weight of graphite and 0.8 % by weight of lubricant combination (see Table 5), in a Lödige mixer for 2 minutes.
- rings with inner diameter of 45 mm, outer diameter 55 mm and a height 10 mm were compacted at three different compaction pressures, 400, 600 and 800 MPa at ambient temperature.
- the resulting ejection energies and densities are shown in Table 5.
- This example demonstrates the lubricating and binding properties of different combinations of amides in powder metal compositions.
- the lubricants had a particle size less than 150 ⁇ m.
- the base powder ASC100.29 was mixed with 2% by weight Cu-100, 0.8 % by weight of graphite and 0,8 % by weight of lubricant/binder combination according to Table 6, in a Lödige mixer for 2 minutes.
- the mixture with EBS was kept as reference while the mixtures comprising amides were heated to a temperature above the melting point of the secondary amide but below the melting point of the primary amide during mixing in another mixer followed by cooling to accomplish bonding of the additives to the iron powder.
- the secondary amide will thus act as a binder and the primary amide will act as a lubricant.
- the melting temperatures of the amides are disclosed in Table 7.
- Samples produced with the aid of the lubricant/binder according to the invention show lower ejection energies compared to samples produced with the lubricant used as reference, i.e. EBS.
- Use of the powder composition comprising the lubricant/binder according to the invention resulted in compacted sintered parts (sintered in 90/10 N 2 /H 2 at 1120°C for 30 minutes) with excellent surface finishes, i.e. essentially without scratches and no stain formation.
- a coarse soft magnetic iron-based powder, wherein the particles are surrounded by an inorganic insulation was mixed with secondary amide lubricant according to Table 9.
- secondary amide lubricant As reference lubricants the known substances Zinc-stearate and EBS were used.
- the particle size distribution of the used iron-based powder is disclosed in Table 10.
- the obtained mixes were transferred to a die and compacted into cylindrical test samples (50 g) having a diameter of 25 mm, in an uniaxial press movement at a compaction pressure of 1100 MPa.
- the die material used was conventional tool steel. During ejection of the compacted samples the ejection force was recorded. The total ejection energy/enveloping area needed in order to eject the samples from the die was calculated.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Powder Metallurgy (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL05783351T PL1812187T3 (pl) | 2004-09-17 | 2005-09-16 | Mieszanka proszków metalicznych zawierająca amidy drugorzędowe pełniące rolę środka poślizgowego i/lub spoiwa |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0402239A SE0402239D0 (sv) | 2004-09-17 | 2004-09-17 | Powder metal composition comprising a lubricant, method for making compacted products using the lubricant, and use of the same |
| SE0500072 | 2005-01-12 | ||
| PCT/SE2005/001343 WO2006031193A1 (en) | 2004-09-17 | 2005-09-16 | Powder metal composition comprising secondary amides as lubricant and/or binder |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP1812187A1 EP1812187A1 (en) | 2007-08-01 |
| EP1812187B1 true EP1812187B1 (en) | 2010-11-10 |
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ID=36060316
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP05783351A Active EP1812187B1 (en) | 2004-09-17 | 2005-09-16 | Powder metal composition comprising secondary amides as lubricant and/or binder |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP1812187B1 (es) |
| JP (1) | JP4887296B2 (es) |
| KR (1) | KR100862785B1 (es) |
| CN (1) | CN101022903B (es) |
| AT (1) | ATE487552T1 (es) |
| BR (1) | BRPI0515368B1 (es) |
| CA (1) | CA2580509C (es) |
| DE (1) | DE602005024708D1 (es) |
| MX (1) | MX2007003194A (es) |
| PL (1) | PL1812187T3 (es) |
| RU (1) | RU2351434C2 (es) |
| WO (1) | WO2006031193A1 (es) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2010285633A (ja) * | 2009-06-09 | 2010-12-24 | Kobe Steel Ltd | 粉末冶金用混合粉末の製造方法、及び焼結体の製造方法 |
| CN103014502A (zh) * | 2012-11-22 | 2013-04-03 | 宁波市群星粉末冶金有限公司 | 汽油发动机活塞粉末冶金材料及制备方法 |
| EP3482852A1 (en) | 2013-09-12 | 2019-05-15 | National Research Council of Canada | Lubricant for powder metallurgy and metal powder compositions containing said lubricant |
| CN105176636A (zh) * | 2014-01-14 | 2015-12-23 | 莱芜市冠隆纳米科技有限公司 | 一种超级润滑剂及其制备方法 |
| GB201409250D0 (en) * | 2014-05-23 | 2014-07-09 | H Gan S Ab Publ | New product |
| KR101664603B1 (ko) | 2014-11-27 | 2016-10-11 | 현대자동차주식회사 | 분말 야금 방법 |
| EP3321002A1 (en) * | 2016-11-15 | 2018-05-16 | Höganäs AB | Feedstock for an additive manufacturing method, additive manufacturing method using the same, and article obtained therefrom |
| US11224914B2 (en) | 2017-06-16 | 2022-01-18 | Jfe Steel Corporation | Powder mixture for powder metallurgy and method of manufacturing same |
| JP6648779B2 (ja) * | 2017-06-16 | 2020-02-14 | Ｊｆｅスチール株式会社 | 粉末冶金用粉末混合物およびその製造方法 |
| RU2645806C1 (ru) * | 2017-06-19 | 2018-02-28 | Юлия Алексеевна Щепочкина | Спеченный антифрикционный материал на основе железа |
| KR20190128427A (ko) | 2018-05-08 | 2019-11-18 | 현대자동차주식회사 | 분말 야금 방법 |
| WO2022259547A1 (ja) * | 2021-06-11 | 2022-12-15 | 昭和電工マテリアルズ株式会社 | 潤滑剤、潤滑剤の組み合わせ、粉末混合物、粉末混合物用原料の組み合わせ及び焼結体の製造方法 |
| EP4105301A1 (en) * | 2021-06-15 | 2022-12-21 | Basf Se | New gasoline additive packages |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE468121B (sv) * | 1991-04-18 | 1992-11-09 | Hoeganaes Ab | Pulverblandning innehaallande basmetallpulver och bindemedel av diamidvax och saett att framstaella blandningen |
| US5256185A (en) * | 1992-07-17 | 1993-10-26 | Hoeganaes Corporation | Method for preparing binder-treated metallurgical powders containing an organic lubricant |
| EP0589088B1 (en) * | 1992-09-25 | 1998-08-12 | Kawasaki Steel Corporation | Iron-based powder mixture and method |
| US5627258A (en) * | 1994-03-14 | 1997-05-06 | Kabushiki Kaisha Komatsu Seisakusho | Binder for use in metal powder injection molding and debinding method by the use of the same |
| DE69505566T2 (de) * | 1995-02-14 | 1999-07-01 | Komatsu Ltd., Tokio/Tokyo | Bindemittel zum spritzgiessen von metallpulver und verfahren zum entbinden |
| JP3509408B2 (ja) * | 1995-08-04 | 2004-03-22 | Ｊｆｅスチール株式会社 | 流動性および成形性に優れた粉末冶金用鉄基粉末混合物およびその製造方法 |
| CA2254734A1 (en) * | 1996-05-13 | 1997-11-20 | The Presmet Corporation | Method for preparing high performance ferrous materials |
| JPH10219303A (ja) * | 1997-02-07 | 1998-08-18 | Sumitomo Metal Mining Co Ltd | 無機物粉末射出成形用組成物および焼結体 |
| JP3445112B2 (ja) * | 1997-09-25 | 2003-09-08 | 日立粉末冶金株式会社 | 粉末冶金における粉末成形方法，成形用金型および押型の潤滑方法 |
| JP2000114018A (ja) * | 1998-09-30 | 2000-04-21 | Nichia Chem Ind Ltd | ボンド磁石用組成物 |
| JP3882490B2 (ja) * | 2000-10-13 | 2007-02-14 | 住友金属鉱山株式会社 | 高耐候性磁石粉の製造方法及び得られる製品 |
| JP4135447B2 (ja) * | 2002-09-17 | 2008-08-20 | 住友金属鉱山株式会社 | 高耐候性磁石粉、ボンド磁石用樹脂組成物及びそれを用いて得られるボンド磁石 |
| US7789934B2 (en) * | 2004-01-20 | 2010-09-07 | Kabushiki Kaisha Kobe Seiko Sho | Lubricant for powder metallurgy, powdery mixture for powder metallurgy, and process for producing sinter |
-
2005
- 2005-09-16 CN CN2005800311616A patent/CN101022903B/zh active Active
- 2005-09-16 CA CA2580509A patent/CA2580509C/en active Active
- 2005-09-16 BR BRPI0515368-9A patent/BRPI0515368B1/pt not_active IP Right Cessation
- 2005-09-16 JP JP2007532287A patent/JP4887296B2/ja active Active
- 2005-09-16 RU RU2007114275/02A patent/RU2351434C2/ru not_active IP Right Cessation
- 2005-09-16 KR KR1020077007022A patent/KR100862785B1/ko active IP Right Grant
- 2005-09-16 DE DE602005024708T patent/DE602005024708D1/de active Active
- 2005-09-16 AT AT05783351T patent/ATE487552T1/de active
- 2005-09-16 PL PL05783351T patent/PL1812187T3/pl unknown
- 2005-09-16 WO PCT/SE2005/001343 patent/WO2006031193A1/en active Application Filing
- 2005-09-16 MX MX2007003194A patent/MX2007003194A/es active IP Right Grant
- 2005-09-16 EP EP05783351A patent/EP1812187B1/en active Active
Non-Patent Citations (1)
| Title |
|---|
| DOROFEEV B. YU. ET AL.: "Formation of properties and interparticular concrescence of hotformed powder materials", 1991, pages 789 - 794 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2580509C (en) | 2010-11-16 |
| BRPI0515368A (pt) | 2008-07-22 |
| EP1812187A1 (en) | 2007-08-01 |
| KR100862785B1 (ko) | 2008-10-13 |
| RU2007114275A (ru) | 2008-10-27 |
| CN101022903A (zh) | 2007-08-22 |
| CN101022903B (zh) | 2010-11-10 |
| DE602005024708D1 (de) | 2010-12-23 |
| PL1812187T3 (pl) | 2011-04-29 |
| BRPI0515368B1 (pt) | 2014-07-29 |
| JP4887296B2 (ja) | 2012-02-29 |
| WO2006031193A1 (en) | 2006-03-23 |
| CA2580509A1 (en) | 2006-03-23 |
| JP2008513602A (ja) | 2008-05-01 |
| RU2351434C2 (ru) | 2009-04-10 |
| MX2007003194A (es) | 2007-05-16 |
| KR20070046958A (ko) | 2007-05-03 |
| ATE487552T1 (de) | 2010-11-15 |
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