EP0406825B1 - Composition de lubrifiant - Google Patents
Composition de lubrifiant Download PDFInfo
- Publication number
- EP0406825B1 EP0406825B1 EP90112761A EP90112761A EP0406825B1 EP 0406825 B1 EP0406825 B1 EP 0406825B1 EP 90112761 A EP90112761 A EP 90112761A EP 90112761 A EP90112761 A EP 90112761A EP 0406825 B1 EP0406825 B1 EP 0406825B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- hydrogen
- formula
- composition according
- benzyl
- alkyl
- 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
- 239000000314 lubricant Substances 0.000 title claims description 19
- 239000000203 mixture Substances 0.000 title claims description 15
- -1 2 -hydroxy- 1,3 -propylene Chemical group 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 150000002431 hydrogen Chemical group 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 12
- 239000003921 oil Substances 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000004982 aromatic amines Chemical class 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000002530 phenolic antioxidant Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 238000010525 oxidative degradation reaction Methods 0.000 claims description 5
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 230000003078 antioxidant effect Effects 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000010705 motor oil Substances 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- UKJARPDLRWBRAX-UHFFFAOYSA-N n,n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine Chemical compound C1C(C)(C)NC(C)(C)CC1NCCCCCCNC1CC(C)(C)NC(C)(C)C1 UKJARPDLRWBRAX-UHFFFAOYSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000010802 sludge Substances 0.000 claims description 2
- 125000006839 xylylene group Chemical group 0.000 claims description 2
- 230000003019 stabilising effect Effects 0.000 claims 1
- 235000019198 oils Nutrition 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000000654 additive Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000002199 base oil Substances 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 3
- IOCLFIGHHOKNTE-UHFFFAOYSA-N 2,2,6,6-tetramethyl-n-(2,2,6,6-tetramethylpiperidin-4-yl)piperidin-4-amine Chemical compound C1C(C)(C)NC(C)(C)CC1NC1CC(C)(C)NC(C)(C)C1 IOCLFIGHHOKNTE-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexamethylene diamine Natural products NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- NISAHDHKGPWBEM-UHFFFAOYSA-N 2-(4-nonylphenoxy)acetic acid Chemical compound CCCCCCCCCC1=CC=C(OCC(O)=O)C=C1 NISAHDHKGPWBEM-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- DIOYAVUHUXAUPX-KHPPLWFESA-N Oleoyl sarcosine Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CC(O)=O DIOYAVUHUXAUPX-KHPPLWFESA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- YSIQDTZQRDDQNF-UHFFFAOYSA-L barium(2+);2,3-di(nonyl)naphthalene-1-sulfonate Chemical compound [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 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 239000006078 metal deactivator Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- VDGDCVKCGHKYJP-UHFFFAOYSA-N n-(3-methoxypropyl)-2,2,6,6-tetramethylpiperidin-4-amine Chemical compound COCCCNC1CC(C)(C)NC(C)(C)C1 VDGDCVKCGHKYJP-UHFFFAOYSA-N 0.000 description 2
- FDAKZQLBIFPGSV-UHFFFAOYSA-N n-butyl-2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CCCCNC1CC(C)(C)NC(C)(C)C1 FDAKZQLBIFPGSV-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 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
- 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
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 description 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- GFRWIVVYEWWPTK-UHFFFAOYSA-N 2-sulfanyl-3h-1,2,3-benzothiadiazole-5-thiol Chemical compound SC1=CC=C2SN(S)NC2=C1 GFRWIVVYEWWPTK-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
- XSPWEFYLCYAXBG-UHFFFAOYSA-N 2-sulfanylbenzotriazole-5-thiol Chemical compound C1=C(S)C=CC2=NN(S)N=C21 XSPWEFYLCYAXBG-UHFFFAOYSA-N 0.000 description 1
- SSADPHQCUURWSW-UHFFFAOYSA-N 3,9-bis(2,6-ditert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound CC(C)(C)C1=CC(C)=CC(C(C)(C)C)=C1OP1OCC2(COP(OC=3C(=CC(C)=CC=3C(C)(C)C)C(C)(C)C)OC2)CO1 SSADPHQCUURWSW-UHFFFAOYSA-N 0.000 description 1
- PZRWFKGUFWPFID-UHFFFAOYSA-N 3,9-dioctadecoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCCCCCCCCCCCC)OCC21COP(OCCCCCCCCCCCCCCCCCC)OC2 PZRWFKGUFWPFID-UHFFFAOYSA-N 0.000 description 1
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- CKRLKUOWTAEKKX-UHFFFAOYSA-N 4,5,6,7-tetrahydro-2h-benzotriazole Chemical compound C1CCCC2=NNN=C21 CKRLKUOWTAEKKX-UHFFFAOYSA-N 0.000 description 1
- IWASLBFJTMJYHF-UHFFFAOYSA-N 5-(2h-benzotriazol-5-ylmethyl)-2h-benzotriazole Chemical compound C1=CC2=NNN=C2C=C1CC1=CC2=NNN=C2C=C1 IWASLBFJTMJYHF-UHFFFAOYSA-N 0.000 description 1
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N Cadaverine Natural products NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-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
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229920003232 aliphatic polyester Polymers 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 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 1
- NMAKPIATXQEXBT-UHFFFAOYSA-N didecyl phenyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OC1=CC=CC=C1 NMAKPIATXQEXBT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 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 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
- 239000004611 light stabiliser Substances 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
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- CVVVRDVGVPWPRM-UHFFFAOYSA-N n,n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)pentane-1,5-diamine Chemical compound C1C(C)(C)NC(C)(C)CC1NCCCCCNC1CC(C)(C)NC(C)(C)C1 CVVVRDVGVPWPRM-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
- 125000001400 nonyl 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])[H] 0.000 description 1
- 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 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 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 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil 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
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/40—Six-membered ring containing nitrogen and carbon only
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
- C10M2215/226—Morpholines
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/30—Heterocyclic compounds
-
- 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
- C10N2040/25—Internal-combustion engines
-
- 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
- C10N2040/25—Internal-combustion engines
- C10N2040/251—Alcohol-fuelled engines
-
- 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
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
-
- 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
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
- C10N2040/28—Rotary engines
Definitions
- the present invention relates to lubricant compositions that are stabilized against oxidative degradation. Stabilization is achieved by adding a sterically hindered amine with a specific structure.
- Organic antioxidants for lubricants are primarily organic sulfur and phosphorus compounds, but also aromatic amines and phenols, especially sterically hindered phenols (see, for example, Ullmanns Encyklopadie der Technische Chemie, 4th edition, Verlag Chemie, Volume 20 (1981); page 541- 43). Sterically hindered amines for stabilizing lubricating oils have also been proposed, e.g. in US-A-4 069 199 or JP-A-85/28496.
- EP-A-356 677 proposes mixtures of aromatic amines and sterically hindered amines as antioxidants for lubricants, it also being possible to add phenolic antioxidants to these mixtures.
- R1, R3, R4, R5 or R6 are C1-C12-alkyl, this can be linear or branched alkyl, e.g. Methyl, ethyl, propyl, isopropyl, butyl, isoamyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl or dodecyl.
- R3 as C1-C18 alkyl can also e.g. Tetradecyl, hexadecyl or octadecyl.
- R1, R4, R5 and R6 as alkyl are preferably unbranched C1-C4 alkyl.
- R2, R3 or R5 are C5-C12-cycloalkyl, this can e.g. Cyclopentyl, cyclohexyl, methylcyclohexyl, cyclooctyl or cyclododecyl, but preferably cyclohexyl.
- R2 or R3 are C2-C5-hydroxyalkyl, this can e.g. 2-Hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl or 2-hydroxybutyl, but preferably 2-hydroxyethyl.
- R3 as C3-C18 alkoxyalkyl can e.g. 2-methoxyethyl, 2-ethoxyethyl, 3-methoxypropyl, 3-ethoxypropyl, 3-isopropoxypropyl, 3-butoxypropyl or 3-dodecyloxypropyl.
- R3 as C4-C20 dialkylaminoalkyl can e.g. 2-Dimethylaminoethyl, 3-dimethylaminopropyl, 3-di (isopropyl) aminopropyl or 3-di (octyl) aminopropyl.
- R6 as C1-C12 alkoxy is preferably C1-C4 alkoxy, especially methoxy or ethoxy.
- Preferred as component (B) is a compound of the formula I in which n is 1 or 2, R is hydrogen, R1 is hydrogen, C1-C4-alkyl, allyl, benzyl, acetyl or -OR5, R2 is hydrogen, C1-C4- Is alkyl or a group of the formula II, R3 if n is 1, is hydrogen, C1-C8-alkyl or C3-C1 Alk-alkoxyalkyl and if n is 2, is C2-C8-alkylene, and R5 C6-C10- Means alkyl, cyclohexyl or benzyl.
- a particularly preferred component (B) is a compound of the formula I in which n is 1 or 2, R is hydrogen, R1 is hydrogen, methyl or acetyl, R2 is hydrogen and R3, if n is 1, is hydrogen or C3-C8- Alkoxyalkyl means, and when n is 2, means C2-C6 alkylene.
- component (B) are the compounds of the formula I in which n is 2 and R3 is C2-C6alkylene.
- the compounds of formula I are known compounds which e.g. in U.S. Patents 3,684,765, 3,904,581 and 4,104,248. They are used as light stabilizers for organic polymers.
- Examples of individual compounds of the formula I are: 2,2,6,6-tetramethyl-4-butylaminopiperidine 2,2,6,6-tetramethyl-4-octylaminopiperidine 2,2,6,6-tetramethyl-4-cyclohexylaminopiperidine 2,2,6,6-tetramethyl-4- (N-hydroxyethylbutylamino) piperidine 2,2,6,6-tetramethyl-4- (3-methoxypropylamino) piperidine 2,2,6,6-tetramethyl-4- (3-dimethylaminopropylamino) piperidine Bis (2,2,6,6-tetramethylpiperidin-4-yl) amine 2,3,6-trimethyl-2,6-diethyl-4-isopropylaminopiperidine 1,2,2,6,6-pentamethyl-4-dodecylaminopiperidine 1,2,2,6,6-pentamethyl-4- (N-methyldodecylamino) piperidine 1-acetyl-2,2,
- Component (A) is a mineral or synthetic base oil, as is common for the preparation of lubricants.
- Synthetic oils can e.g. Esters of polycarboxylic acids or of polyols, they can be aliphatic polyesters or poly- ⁇ -olefins, silicones, phosphoric acid esters or polyalkylene glycols.
- the lubricant can also be a grease based on an oil and a thickener. Such lubricants are e.g. described in D. Klamann "Lubricants and related products", Verlag Chemie, Weinheim 1982.
- Component (B) is preferably added to the base oil in an amount of 0.05 to 5, in particular 0.1 to 2% by weight, based on the base oil.
- the addition can take place directly or a concentrated solution of (B) in the oil or in another solvent is first prepared and this solution is added to the oil.
- the lubricant composition may additionally contain other additives such as e.g. Phosphorus III esters, metal deactivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants, surfactants or wear protection additives.
- additives e.g. Phosphorus III esters, metal deactivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants, surfactants or wear protection additives.
- Examples of phosphorus III esters are: Triphenyl phosphite, decyl diphenyl phosphite, phenyl didecyl phosphite, tris- (nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, distearyl-pentaerythritol diphosphite, tris- (2,4-di-tert.butylphenyl) -phosphite, diisodechritol , 4-di-tert.butylphenyl) pentaerythritol diphosphite, tristearyl sorbitol triphosphite, tetrakis (2,4-di-tert.butylphenyl) -4,4′-biphenylene diphosphonite, bis- (2,6-di- tert-butyl-4
- metal deactivators for example for copper
- Triazoles Triazoles, benzotriazoles and their derivatives, tolutriazoles and their derivatives, 2-mercaptobenzthiazole, 2-mercaptobenztriazole, 2,5-dimercaptobenztriazole, 2,5-dimercaptobenzthiadiazole, 5,5'-methylenebisbenzotriazole, 4,5,6,7-tetrahydrobenztriazole, salicylides -propylenediamine, salicylaminoguanidine and its salts.
- viscosity index improvers are: Polyacrylates, polymethacrylates, vinyl pyrrolidone / methacrylate copolymers, polyvinyl pyrrolidones, polybutenes, olefin copolymers, styrene / acrylate copolymers, polyethers.
- pour point depressants are: Polymethacrylate, alkylated naphthalene derivatives.
- dispersants / surfactants are: Polybutenylsuccinic acid amides or imides, polybutenylphosphonic acid derivatives, basic magnesium, calcium and barium sulfonates and phenolates.
- wear protection additives are: Compounds containing sulfur and / or phosphorus and / or halogen, such as sulfurized vegetable oils, zinc dialkyldithiophosphates, tritolyl phosphate, chlorinated paraffins, alkyl and aryl di- and tri-sulfides, triphenyl phosphorothionates, diethanolaminomethyltolyltriazole, di (2-ethyltylylolyl) aminol.
- sulfurized vegetable oils such as sulfurized vegetable oils, zinc dialkyldithiophosphates, tritolyl phosphate, chlorinated paraffins, alkyl and aryl di- and tri-sulfides, triphenyl phosphorothionates, diethanolaminomethyltolyltriazole, di (2-ethyltylylolyl) aminol.
- the lubricant can also contain solid lubricants, such as graphite or molybdenum sulfide.
- Table 1 shows the induction times. The longer the induction time, the higher the antioxidant effect of the tested stabilizer.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Claims (9)
- Composition lubrifiante qui contient :(A) une huile minérale ou synthétique ou un mélange de telles huiles et(B) comme stabilisant contre l'oxydation une amine à empêchement stérique répondant à la formule I :
n est égal à 1 ou à 2,
R représente l'hydrogène ou un méthyle,
R₁ représente l'hydrogène, un alkyle en C₁-C₁₂, un allyle, un benzyle ou un radical -CO-R₄, -OR₅ ou -O-CO-R₆,
R₂ représente l'hydrogène, un alkyle en C₁-C₁₂, un cycloalkyle en C₅-C₁₂, un hydroxyalkyle en C₂-C₅ ou un radical de formule II :
- lorsque n est égal à 1 : l'hydrogène, un alkyle en C₁-C₁₈, un cycloalkyle en C₅-C₁₂, un hydroxyalkyle en C₂-C₅, un alcoxyalkyle en C₃-C₁₈ ou un dialkylamino-alkyle en C₄-C₂₀, et- lorsque n est égal à 2 : un alkylène en C₂-C₁₂, un 2-hydroxy-1,3-propylène ou un xylylène,R₄ représente l'hydrogène, un alkyle en C₁-C₁₂ ou un phényle,
R₅ représente l'hydrogène, un alkyle en C₁-C₁₂, un cycloalkyle en C₅-C₁₂ ou un benzyle, et
R₆ représente un alkyle en C₁-C₁₂, un alcoxy en C₁-C₁₂ ou un phényle,
et qui ne contient ni amine aromatique ni anti-oxydant phénolique. - Composition selon la revendication 1, caractérisée en ce que (B) est un composé de formule I dans lequel n est égal à 1 ou à 2, R représente l'hydrogène, R₁ représente l'hydrogène, un alkyle en C₁-C₄, un allyle, un benzyle, un acétyle ou un radical -OR₅, R₂ représente l'hydrogène, un alkyle en C₁-C₄ ou un radical de formule II, R₃ représente, lorsque n est égal à 1, l'hydrogène, un alkyle en C₁-C₈ ou un alcoxyalkyle en C₃-C₁₀ et, lorsque n est égal à 2, un alkylène en C₂-C₈, et R₅ représente un alkyle en C₆-C₁₀, un cyclohexyle ou un benzyle.
- Composition selon la revendication 1, caractérisée en ce que (B) est un composé de formule I dans lequel n est égal à 1 ou à 2, R représente l'hydrogène, R₁ représente l'hydrogène, un méthyle ou un acétyle, R₂ représente l'hydrogène et R₃ représente, lorsque n est égal à 1, l'hydrogène ou un alcoxyalkyle en C₃-C₈ et, lorsque n est égal à 2, un alkylène en C₂-C₆.
- Composition selon la revendication 3, caractérisée en ce que (B) est un composé de formule I dans lequel n est égal à 2 et R₃ représente un alkylène en C₂-C₆.
- Composition selon la revendication 4, dans lequel (B) est la N,N′-bis-(2,2,6,6-tétraméthyl-pipéridine-4-yl)hexaméthylène-diamine.
- Composition selon la revendication 1 qui contient de 0,1 à 2 % en poids de (B) par rapport à (A).
- Application d'une composition selon la revendication 1 comme huile de moteur
- Application de composés de formule I tels que définis à la revendication 1 pour la stabilisation de lubrifiants contre la dégradation par oxydation, les lubrifiants ne contenant ni amine aromatique ni d'anti-oxydant phénolique.
- Application de composés de formule I tels que définis à la revendication 1 pour diminuer la formation de boues dans des huiles de moteur, les huiles ne contenant ni amine aromatique ni anti-oxydant phénolique.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2529/89 | 1989-07-07 | ||
| CH252989 | 1989-07-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0406825A1 EP0406825A1 (fr) | 1991-01-09 |
| EP0406825B1 true EP0406825B1 (fr) | 1993-03-03 |
Family
ID=4235853
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP90112761A Expired - Lifetime EP0406825B1 (fr) | 1989-07-07 | 1990-07-04 | Composition de lubrifiant |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0406825B1 (fr) |
| JP (1) | JPH0345695A (fr) |
| CA (1) | CA2020552A1 (fr) |
| DE (1) | DE59000955D1 (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014017182A1 (fr) | 2012-07-27 | 2014-01-30 | Ｊｘ日鉱日石エネルギー株式会社 | Composition d'huile lubrifiante, et procédé de lubrification de matière de glissement tout en empêchant l'élution de cuivre et de plomb |
| CN105874043B (zh) | 2013-11-04 | 2022-05-24 | 巴斯夫欧洲公司 | 润滑剂组合物 |
| WO2016156328A1 (fr) * | 2015-03-31 | 2016-10-06 | Shell Internationale Research Maatschappij B.V. | Utilisation d'une composition lubrifiante comprenant un photostabilisant de type amine encombrée pour une meilleure propreté d'un piston dans un moteur à combustion interne |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3480635A (en) * | 1966-09-28 | 1969-11-25 | Universal Oil Prod Co | N-piperidyl substituted phenylenediamines |
| CA1084035A (fr) * | 1976-04-01 | 1980-08-19 | Warren Lowe | Additifs antioxydants pour huile de graissage |
| EP0253007A1 (fr) * | 1986-07-15 | 1988-01-20 | The B.F. GOODRICH Company | Stabilisants pour polymères, polymères stabilisés, leur synthèse |
| US4398505A (en) * | 1981-10-22 | 1983-08-16 | Standard Oil Company (Indiana) | Diesel fuel composition |
| US4607104A (en) * | 1985-07-11 | 1986-08-19 | Uniroyal Chemical Company, Inc. | Process for the production of 2,2,6,6-tetraalkyl-4-piperidylamines |
| ATE92916T1 (de) * | 1987-04-08 | 1993-08-15 | Ciba Geigy Ag | Schwefelhaltige verbindungen als antioxidantien fuer schmiermittel und elastomere. |
| IT1222394B (it) * | 1987-07-30 | 1990-09-05 | Ciba Geigy Spa | Processo per la preparazione di 2,2,6,6 tetrametil 4 piperidilammine |
| DE3738736A1 (de) * | 1987-11-14 | 1989-05-24 | Basf Ag | 4-formylaminopiperidinderivate und deren verwendung als stabilisatoren |
| US5073278A (en) * | 1988-07-18 | 1991-12-17 | Ciba-Geigy Corporation | Lubricant composition |
-
1990
- 1990-07-04 EP EP90112761A patent/EP0406825B1/fr not_active Expired - Lifetime
- 1990-07-04 DE DE9090112761T patent/DE59000955D1/de not_active Expired - Fee Related
- 1990-07-05 CA CA002020552A patent/CA2020552A1/fr not_active Abandoned
- 1990-07-06 JP JP2179384A patent/JPH0345695A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA2020552A1 (fr) | 1991-01-08 |
| DE59000955D1 (de) | 1993-04-08 |
| JPH0345695A (ja) | 1991-02-27 |
| EP0406825A1 (fr) | 1991-01-09 |
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