EP0000514B1 - Esters phénoliques N, N-dioctyliques d'acide dithiocarbamique et lubrifiants stabilisés les contenant - Google Patents
Esters phénoliques N, N-dioctyliques d'acide dithiocarbamique et lubrifiants stabilisés les contenant Download PDFInfo
- Publication number
- EP0000514B1 EP0000514B1 EP78100387A EP78100387A EP0000514B1 EP 0000514 B1 EP0000514 B1 EP 0000514B1 EP 78100387 A EP78100387 A EP 78100387A EP 78100387 A EP78100387 A EP 78100387A EP 0000514 B1 EP0000514 B1 EP 0000514B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- formula
- compound
- stabiliser
- lubricants
- 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
Links
- 239000000314 lubricant Substances 0.000 title claims description 29
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 title claims description 4
- -1 C5-C7-cycloalkyl Chemical group 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 22
- 239000003381 stabilizer Substances 0.000 claims description 20
- 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 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000002480 mineral oil Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- NTXAPVRHEOEJDE-UHFFFAOYSA-N CCCCCCCCN(CCCCCCCC)C([SH2]CC(C=C1C(C)(C)C)=CC(C(C)(C)C)=C1O)=S Chemical compound CCCCCCCCN(CCCCCCCC)C([SH2]CC(C=C1C(C)(C)C)=CC(C(C)(C)C)=C1O)=S NTXAPVRHEOEJDE-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 238000012360 testing method Methods 0.000 description 10
- 239000000654 additive Substances 0.000 description 8
- 239000003963 antioxidant agent Substances 0.000 description 7
- 235000006708 antioxidants Nutrition 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000012990 dithiocarbamate Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- 0 CC(C)(C)C(C1)*C1N Chemical compound CC(C)(C)C(C1)*C1N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 125000003764 2,4-dimethylpentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 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 description 2
- 239000002270 dispersing agent Substances 0.000 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 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 230000009021 linear effect Effects 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WPHVRMGBXBGKTC-UHFFFAOYSA-N 1,2-dioctyl-10h-phenothiazine Chemical compound C1=CC=C2NC3=C(CCCCCCCC)C(CCCCCCCC)=CC=C3SC2=C1 WPHVRMGBXBGKTC-UHFFFAOYSA-N 0.000 description 1
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- XEGAKAFEBOXGPV-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-benzotriazole Chemical compound C1C=CC=C2NNNC12 XEGAKAFEBOXGPV-UHFFFAOYSA-N 0.000 description 1
- HVFKKINZIWVNQG-UHFFFAOYSA-N 2,4,6-tri(propan-2-yl)phenol Chemical compound CC(C)C1=CC(C(C)C)=C(O)C(C(C)C)=C1 HVFKKINZIWVNQG-UHFFFAOYSA-N 0.000 description 1
- VNMNRMBWSGJGAT-UHFFFAOYSA-N 2-(dichloromethyl)phenol Chemical class OC1=CC=CC=C1C(Cl)Cl VNMNRMBWSGJGAT-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- FPEANFVVZUKNFU-UHFFFAOYSA-N 2-sulfanylbenzotriazole Chemical compound C1=CC=CC2=NN(S)N=C21 FPEANFVVZUKNFU-UHFFFAOYSA-N 0.000 description 1
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 1
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 1
- MDWVSAYEQPLWMX-UHFFFAOYSA-N 4,4'-Methylenebis(2,6-di-tert-butylphenol) Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 MDWVSAYEQPLWMX-UHFFFAOYSA-N 0.000 description 1
- WODZSHMAILHEGD-UHFFFAOYSA-N 6-tert-butyl-3-(chloromethyl)-2,4-dimethylphenol Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CCl WODZSHMAILHEGD-UHFFFAOYSA-N 0.000 description 1
- UUNBFTCKFYBASS-UHFFFAOYSA-N C(CCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCC Chemical compound C(CCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCC UUNBFTCKFYBASS-UHFFFAOYSA-N 0.000 description 1
- WPHGSKGZRAQSGP-UHFFFAOYSA-N C1C2C1CCCC2 Chemical compound C1C2C1CCCC2 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 description 1
- 125000000172 C5-C10 aryl group Chemical group 0.000 description 1
- YICVREMECZTJHO-UHFFFAOYSA-N CCN(CC)C([SH2]CC1=CC=CC=C1)=S Chemical compound CCN(CC)C([SH2]CC1=CC=CC=C1)=S YICVREMECZTJHO-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 1
- 239000003508 Dilauryl thiodipropionate Substances 0.000 description 1
- 238000004252 FT/ICR mass spectrometry Methods 0.000 description 1
- 241001076195 Lampsilis ovata Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- 239000003490 Thiodipropionic acid Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007866 anti-wear additive Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- YSIQDTZQRDDQNF-UHFFFAOYSA-L barium(2+);2,3-di(nonyl)naphthalene-1-sulfonate Chemical class [Ba+2].C1=CC=C2C(S([O-])(=O)=O)=C(CCCCCCCCC)C(CCCCCCCCC)=CC2=C1.C1=CC=C2C(S([O-])(=O)=O)=C(CCCCCCCCC)C(CCCCCCCCC)=CC2=C1 YSIQDTZQRDDQNF-UHFFFAOYSA-L 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- RUTWCOZYFYYRSL-UHFFFAOYSA-N benzyl(hydroxy)carbamodithioic acid Chemical class SC(=S)N(O)CC1=CC=CC=C1 RUTWCOZYFYYRSL-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- GLOQRSIADGSLRX-UHFFFAOYSA-N decyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCCCC)OC1=CC=CC=C1 GLOQRSIADGSLRX-UHFFFAOYSA-N 0.000 description 1
- 235000019304 dilauryl thiodipropionate Nutrition 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000010688 mineral lubricating oil Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- FSWDLYNGJBGFJH-UHFFFAOYSA-N n,n'-di-2-butyl-1,4-phenylenediamine Chemical compound CCC(C)NC1=CC=C(NC(C)CC)C=C1 FSWDLYNGJBGFJH-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- PUUARXRJNUGOBB-UHFFFAOYSA-N octyl 2-(2-octoxy-2-oxoethyl)sulfanylacetate Chemical compound CCCCCCCCOC(=O)CSCC(=O)OCCCCCCCC PUUARXRJNUGOBB-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- OLBCVFGFOZPWHH-UHFFFAOYSA-N propofol Chemical compound CC(C)C1=CC=CC(C(C)C)=C1O OLBCVFGFOZPWHH-UHFFFAOYSA-N 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 150000003329 sebacic acid derivatives Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000010689 synthetic lubricating oil Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- QUTZUATVZPXUJR-UHFFFAOYSA-N trinonyl phosphite Chemical compound CCCCCCCCCOP(OCCCCCCCCC)OCCCCCCCCC QUTZUATVZPXUJR-UHFFFAOYSA-N 0.000 description 1
- 239000010723 turbine oil Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/12—Thio-acids; Thiocyanates; Derivatives thereof
- C10M135/14—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond
- C10M135/18—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond thiocarbamic type, e.g. containing the groups
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/084—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/085—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives thereof
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- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/086—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing sulfur atoms bound to carbon atoms of six-membered aromatic rings
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/089—Overbased salts
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/09—Heterocyclic compounds containing no sulfur, selenium or tellurium compounds in the ring
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/108—Phenothiazine
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/041—Triaryl phosphates
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/043—Ammonium or amine salts thereof
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/045—Metal containing thio derivatives
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/10—Groups 5 or 15
Definitions
- the present invention relates to lubricants stabilized with phenol-N, N-dioctyl-dithio-carbamates, or to the use of phenol-N, N-dioctyl-dithiocarbamates for stabilizing lubricants.
- additives are generally added to mineral and synthetic lubricants to improve their performance properties.
- additives which are intended to protect the devices to be lubricated from frictional wear.
- wear inhibitors are required to increase the load-bearing capacity of the lubricant and not to have a corrosive effect on the metal parts to be protected.
- Alkyl-substituted phenols and dithiocarbams such as the already widely used commercial products 2,6-di-tert-butyl-4-methylphenol or S-benzyl-N, N-diethyldithiocarbamate, are already generally known in the lubricant sector as antioxidants.
- US Pat. No. 3,412,026 describes a lubricant composition containing a small proportion of a mixture of antimony-N, N-dialkyldithiocarbamate and dialkylhydroxybenzyl-N, N-diphenyl-dithiocarbamate with good stability.
- GB-A-1 024 651 describes metal salts of carbamides containing 2,6-dialkylphenol which are to be used as antioxidants and antiwear additives in lubricants. However, it was found that the effects of these metal salt additives are impaired by the formation of residues. W.M. Denton, "Screening of Compounds for Anti-Oxidant Activity in Motor Oil," Inst. Of Pet Review, 2/66, 46-54, describes S- (3,5-di-tert-butyl-4-hydroxy- benzyl) -N, N-di-n-butyl-dithiocarbamate as a lubricant additive.
- the dithiocarbamate group is bonded to the phenol ring in the o- or in particular in the m- or p-, but preferably in the p-position to the hydroxyl group.
- Lubricants which are a stabilizer are a compound of the formula contain, wherein R and R 1 are C 1 -C 4 alkyl.
- lubricants that act as a stabilizer, a compound of the formula included, wherein R and R 1 are C 1 -C 4 alkyl.
- the invention also relates to compounds of the formula wherein RC 1 -C 1Z alkyl, C 5 -C 7 cycloalkyl, C 6 -C 10 aryl optionally substituted by C 1 -C 6 alkyl, C 7 -C 22 aralkyl and R 1 and R 2 each independently represent H or R. .
- hydroxybenzyl-N, N-dioctyl-dithiocarbamates to be used according to the invention can be obtained by generally known methods, for example by using mono- or di-chloromethylphenols of the formulas with the equivalent amounts of corresponding Na dithiocarbamates of the formula in an inert solvent such as acetonitrile, toluene, ether or chloroform with the elimination of NaCl.
- an inert solvent such as acetonitrile, toluene, ether or chloroform with the elimination of NaCl.
- the ortho- and in particular the para-hydroxybenzyl-dithiocarbamates can be obtained analogously in the manner cited above for the meta derivatives, but they are preferably prepared by known methods by reacting molar amounts of a corresponding substituted phenol of the formula. with formaldehyde, carbon disulfide and an amine of the formula
- the compounds of the formula act as stabilizers against the oxidation and corrosion effects in lubricants.
- Mineral and synthetic lubricating oils and mixtures thereof which contain 0.001 to 5% by weight, based on the lubricant, and preferably 0.02-3% of a compound of the formula I, have excellent lubricating properties, which are due to greatly reduced wear and tear on the lubricants Friction partners become clear.
- lubricants in question are familiar to the person skilled in the art and e.g. in the "Lubricant Pocket Book” (Hüthig Verlag, Heidelberg, 1974). Mineral oils are particularly suitable.
- the lubricating oil formulation can additionally contain other additives that are added to improve certain performance properties, such as antioxidants, metal passivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants / surfactants and other wear protection additives.
- additives such as antioxidants, metal passivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants / surfactants and other wear protection additives.
- antioxidants are:
- metal passivators examples are:
- Polymethacrylates vinyl pyrrolidone methacrylate copolymers, polybutenes, olefin copolymers, styrene / acrylate copolymers.
- pour point depressants examples are:
- dispersants / surfactants are polybutenyl succinic acid imides.
- Compounds containing sulfur and / or phosphorus and / or halogen such as sulfurized vegetable oils, zinc dialkyldithiophosphates, tritolyl phosphate, chlorinated paraffins, alkyl and aryl disulfides.
- Example 1 S- (3-Hydroxy-4-tert-butyl-2,6-dimethylbenzyl) -N, N-di-n-octyldithiocarbamate.
- the mixture is then poured into about 1 liter of ice water, the toluene phase is separated off after the addition of a further 100 ml of toluene, shaken out with water, dried over calcium chloride and evaporated in vacuo.
- the S- (3-hydroxy-4-tert-butyl-2,6-dimethylbenzyl) -N, N-di-n-octyl-dithiocarbamate remains as a brownish viscous oil and is already sufficiently pure and suitable for use as a stabilizer elementary analytical and chromatographic largely uniform.
- di-n-octyl (Example 2) to be used according to the invention and the di-n-butyl (Example 3) derivatives to be compared are listed in the following table. They are obtained by known methods, preferably by reacting appropriate phenols (column 2 of the table) with formaldehyde, carbon disulfide and the corresponding secondary amine (column 3 of the table) (for example according to US Pat. No. 2,757,174).
- Example 5 Oil Oxidation Test, Standard Version According to ASTM D 2272 (Rotary Bomb Oxidation Test)
- the glass vessel is in a stainless steel bomb with a pressure gauge.
- the bomb rotates axially at 100 rpm. at an angle of 30 ° to the horizontal, in an oil bath at 150 ° C.
- the oxygen pressure is initially around 6 atm (90 psi) before heating, rises to 150 ° C to just under 14 atm (200 psi) and remains constant until oxidation begins.
- the test is complete when the pressure drops by 1.7 Atm (25 psi). The time is recorded in minutes.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (12)
1. Lubrifiants contenant, comme stabilisant, un composé répondant à la formule I
dans laquelle
R représente un alkyle en C1-C12, un cycloalkyle en C5-C7, un aryle en C6-C10 éventuellement porteur d'un alkyle en C1-C6, ou un aralkyle en C7-C22,
R1 et R2 représentent chacun, indépendamment l'un de l'autre, H ou R et
R3 représente un octyle.
2. Lubrifiants selon la revendication 1, caractérisés en ce qu'ils contiennent, comme stabilisant, un composé de formule 1 dans lequel:
R et R1 représentent chacun un alkyle en C1-C8, un phényle ou un benzyle,
R2 représente l'hydrogène ou un alkyle en C1-C8 et
R3 représente un octyle,
et dans lequel le groupe dithiocarbamate est en position méta ou en position para relativement au groupe hydroxy du phénol.
3. Lubrifiants selon la revendication 1, caractérisés en ce qu'ils contiennent, comme stabilisant, un composé répondant à la formule IV
dans laquelle
R et RI représentent chacun un radical alkyle en C1-C4 et
R2 représente l'hydrogène ou le radical méthyle.
4. Lubrifiants selon la revendication 1, caractérisés en ce qu'ils contiennent, comme stabilisant, un composé de formule
dans laquelle R et RI représentent chacun un radical alkyle contenant de 1 à 4 atomes de carbone.
5. Lubrifiants selon la revendication 1, caractérisés en ce qu'ils contiennent, comme stabilisant, un composé de formule
dans laquelle R et R1 représentent chacun un alkyle en C1-C4.
6. Lubrifiants selon la revendication 1, caractérisés en ce qu'ils contiennent, comme stabilisant, le N,N-di-n-octyl-dithiocarbamate de S-(hydroxy-3-tert-butyl-4 diméthyl-2,6 benzyle).
7. Lubrifiants selon la revendication 1, caractérisés en ce qu'ils contiennent, comme stabilisant, le N,N-di-n-octyl-dithiocarbamate de S-(di-tert-butyl-3,5 hydroxy-4 benzyle).
8. Application de composés de formule I comme stabilisants de lubrifiants selon la revendication 1.
9. Application de composés de formule 1 comme stabilisants d'huiles minérales selon la revendication 1.
10. Composés répondant à la formule
dans laquelle
R représente un alkyle en C1-C12, un cycloalkyle en C5-C7, un aryle en C6-C10 éventuellement . porteur d'un alkyle en C1-C6, ou un aralkyle en C7-C22, et
R, et R2 représentent chacun, indépendamment l'un de l'autre, H ou R.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH9061/77 | 1977-07-21 | ||
| CH906177 | 1977-07-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0000514A1 EP0000514A1 (fr) | 1979-02-07 |
| EP0000514B1 true EP0000514B1 (fr) | 1982-01-13 |
Family
ID=4347895
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP78100387A Expired EP0000514B1 (fr) | 1977-07-21 | 1978-07-13 | Esters phénoliques N, N-dioctyliques d'acide dithiocarbamique et lubrifiants stabilisés les contenant |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4225450A (fr) |
| EP (1) | EP0000514B1 (fr) |
| JP (1) | JPS5422414A (fr) |
| CA (1) | CA1102782A (fr) |
| DE (1) | DE2861529D1 (fr) |
| IT (1) | IT1097362B (fr) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4734210A (en) * | 1985-07-30 | 1988-03-29 | Ciba-Geigy Corporation | Additives for lubricant compositions |
| US4836942A (en) * | 1988-06-06 | 1989-06-06 | Ethyl Petroleum Additives, Inc. | Lubricant composition |
| US5084195A (en) * | 1988-12-28 | 1992-01-28 | Ciba-Geigy Corporation | Lubricant composition comprising an allophanate extreme-pressure, anti-wear additive |
| US5370806A (en) * | 1989-12-21 | 1994-12-06 | Mobil Oil Corporation | Borated dihydrocarbyl dithiocarbamate lubricant additives and composition thereof |
| US5560853A (en) * | 1990-08-30 | 1996-10-01 | Pennzoil Products Company | Dithiocarbamoyl diols and borate esters thereof for use in lubricant compositions |
| US5254275A (en) * | 1991-12-12 | 1993-10-19 | Exxon Research And Engineering Company | Lubricating oil containing an O-alkyl-N-alkoxycarbonylthionocarbamate (PNE-633) |
| US6046144A (en) * | 1997-06-02 | 2000-04-04 | R.T. Vanderbilt Co., Inc. | Combination of phosphate based additives and sulfonate salts for hydraulic fluids and lubricating compositions |
| US7112558B2 (en) | 2002-02-08 | 2006-09-26 | Afton Chemical Intangibles Llc | Lubricant composition containing phosphorous, molybdenum, and hydroxy-substituted dithiocarbamates |
| US7741257B2 (en) | 2005-03-15 | 2010-06-22 | Ecolab Inc. | Dry lubricant for conveying containers |
| US7745381B2 (en) | 2005-03-15 | 2010-06-29 | Ecolab Inc. | Lubricant for conveying containers |
| US7915206B2 (en) * | 2005-09-22 | 2011-03-29 | Ecolab | Silicone lubricant with good wetting on PET surfaces |
| US7727941B2 (en) * | 2005-09-22 | 2010-06-01 | Ecolab Inc. | Silicone conveyor lubricant with stoichiometric amount of an acid |
| US7741255B2 (en) * | 2006-06-23 | 2010-06-22 | Ecolab Inc. | Aqueous compositions useful in filling and conveying of beverage bottles wherein the compositions comprise hardness ions and have improved compatibility with pet |
| CN104987944A (zh) | 2010-09-24 | 2015-10-21 | 艺康美国股份有限公司 | 包括乳液的输送机润滑剂和使用它们的方法 |
| CA2829492A1 (fr) * | 2011-03-10 | 2012-09-13 | Yanshi Zhang | Composition lubrifiante contenant un thiocarbamate |
| AU2014249350B2 (en) | 2013-03-11 | 2017-11-30 | Ecolab Usa Inc. | Lubrication of transfer plates using an oil or oil in water emulsions |
| CN105601551B (zh) * | 2014-11-24 | 2017-08-22 | 中国石油化工股份有限公司 | 一种含硫受阻酚类化合物及其制备方法和应用 |
| CN104611094B (zh) * | 2015-01-30 | 2017-02-22 | 西安热工研究院有限公司 | 一种汽轮机油复合抗氧剂及其制备方法与添加方法 |
| CN111040823B (zh) * | 2020-01-02 | 2022-06-28 | 济南佳进新材料有限公司 | 抗磨剂、其应用、其制备方法、无灰液压油组合物及其制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB966224A (en) * | 1960-10-06 | 1964-08-06 | Canadian Ind | Hydroxybenzyl dithiocarbamates and stabilization of olefine polymers |
| BE625612A (fr) | 1962-01-03 | |||
| NL298236A (fr) | 1962-09-24 | |||
| FR1482630A (fr) * | 1965-06-09 | 1967-05-26 | Us Rubber Co | Composés chimiques à action fongicide ou bactéricide pour l'agriculture ou l'industrie |
| GB1125900A (en) | 1966-08-30 | 1968-09-05 | Ici Ltd | Stabilisation of resin |
| US3412026A (en) * | 1966-12-12 | 1968-11-19 | Shell Oil Co | Lubricant compositions containing dithiocarbamates |
| US3462368A (en) * | 1967-02-27 | 1969-08-19 | Ethyl Corp | Hydrocarbyl-hydroxyphenyl dithiocarbamates and their use as antioxidants |
-
1978
- 1978-07-13 DE DE7878100387T patent/DE2861529D1/de not_active Expired
- 1978-07-13 US US05/924,416 patent/US4225450A/en not_active Expired - Lifetime
- 1978-07-13 EP EP78100387A patent/EP0000514B1/fr not_active Expired
- 1978-07-19 CA CA307,663A patent/CA1102782A/fr not_active Expired
- 1978-07-20 IT IT25943/78A patent/IT1097362B/it active
- 1978-07-21 JP JP8927578A patent/JPS5422414A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2861529D1 (en) | 1982-02-25 |
| JPS6250520B2 (fr) | 1987-10-26 |
| IT7825943A0 (it) | 1978-07-20 |
| IT1097362B (it) | 1985-08-31 |
| JPS5422414A (en) | 1979-02-20 |
| EP0000514A1 (fr) | 1979-02-07 |
| CA1102782A (fr) | 1981-06-09 |
| US4225450A (en) | 1980-09-30 |
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