EP0079302A2 - Lubrifiant contenant des thioéthers de composés bêta-dicarbonyles ou bêta cyanocarbonyles - Google Patents

Lubrifiant contenant des thioéthers de composés bêta-dicarbonyles ou bêta cyanocarbonyles Download PDF

Info

Publication number: EP0079302A2
Authority: EP; European Patent Office
Prior art keywords: beta; group; formula; alkyl; compounds
Prior art date: 1981-10-29
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

EP82810441A

Other languages

German (de)

English (en)

Inventor

Hermann O. Dr. Wirth

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Original Assignee

Ciba Geigy AG

Priority date (The priority date 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 date listed.)

1981-10-29

Filing date

1982-10-25

Publication date

1983-05-18

1982-10-25 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1983-05-18 Publication of EP0079302A2 publication Critical patent/EP0079302A2/fr

Status Withdrawn legal-status Critical Current

Links

239000000314 lubricant Substances 0.000 title claims description 21
150000003568 thioethers Chemical class 0.000 title abstract description 7
150000001875 compounds Chemical class 0.000 claims abstract description 25
239000003921 oil Substances 0.000 claims abstract description 12
229910052751 metal Inorganic materials 0.000 claims abstract description 7
239000002184 metal Substances 0.000 claims abstract description 7
239000012190 activator Substances 0.000 claims abstract description 4
239000000654 additive Substances 0.000 claims description 19
-1 1,1,3,3-tetramethylbutyl Chemical group 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 14
230000000996 additive effect Effects 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
239000003879 lubricant additive Substances 0.000 abstract description 3
239000005069 Extreme pressure additive Substances 0.000 abstract 1
239000007866 anti-wear additive Substances 0.000 abstract 1
125000001424 substituent group Chemical group 0.000 abstract 1
235000019198 oils Nutrition 0.000 description 10
239000002253 acid Substances 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
238000009472 formulation Methods 0.000 description 5
239000002199 base oil Substances 0.000 description 4
239000003112 inhibitor Substances 0.000 description 4
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000003963 antioxidant agent Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000000034 method Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
229910019142 PO4 Inorganic materials 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
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 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
239000002173 cutting fluid Substances 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
238000005555 metalworking Methods 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
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
239000012188 paraffin wax Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
229910052698 phosphorus Inorganic materials 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
231100000241 scar Toxicity 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
229910052717 sulfur Inorganic materials 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
238000003466 welding Methods 0.000 description 2
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
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
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
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 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
MQWCQFCZUNBTCM-UHFFFAOYSA-N 2-tert-butyl-6-(3-tert-butyl-2-hydroxy-5-methylphenyl)sulfanyl-4-methylphenol Chemical compound CC(C)(C)C1=CC(C)=CC(SC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O MQWCQFCZUNBTCM-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
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
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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 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
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 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
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-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
DIOYAVUHUXAUPX-KHPPLWFESA-N Oleoyl sarcosine Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CC(O)=O DIOYAVUHUXAUPX-KHPPLWFESA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
BGTLSDQMKYQERJ-UHFFFAOYSA-M [Zn+].CCCCCOP([O-])(=S)SCCCCC Chemical compound [Zn+].CCCCCOP([O-])(=S)SCCCCC BGTLSDQMKYQERJ-UHFFFAOYSA-M 0.000 description 1
239000000370 acceptor Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
150000004982 aromatic amines Chemical class 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
ACNHBJQDDXQFAT-UHFFFAOYSA-K bis(dipentylcarbamothioylsulfanyl)stibanyl n,n-dipentylcarbamodithioate Chemical compound CCCCCN(CCCCC)C(=S)S[Sb](SC(=S)N(CCCCC)CCCCC)SC(=S)N(CCCCC)CCCCC ACNHBJQDDXQFAT-UHFFFAOYSA-K 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 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
235000019304 dilauryl thiodipropionate Nutrition 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
230000000694 effects Effects 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
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
150000002462 imidazolines Chemical class 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 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
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
239000011707 mineral Substances 0.000 description 1
239000010688 mineral lubricating oil Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
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 1
150000002790 naphthalenes Chemical class 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229910052757 nitrogen Inorganic materials 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
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
150000002918 oxazolines Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
150000004707 phenolate Chemical class 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229920001083 polybutene Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
KOODSCBKXPPKHE-UHFFFAOYSA-N propanethioic s-acid Chemical compound CCC(S)=O KOODSCBKXPPKHE-UHFFFAOYSA-N 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
150000003329 sebacic acid derivatives Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 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
235000015096 spirit Nutrition 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
239000010689 synthetic lubricating oil Substances 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 1
QUTZUATVZPXUJR-UHFFFAOYSA-N trinonyl phosphite Chemical compound CCCCCCCCCOP(OCCCCCCCCC)OCCCCCCCCC QUTZUATVZPXUJR-UHFFFAOYSA-N 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
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/08—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic sulfur-, selenium- or tellurium-containing compound
- 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
- C10M131/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen
- C10M131/14—Halogenated waxes
- 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
- C10M135/20—Thiols; Sulfides; Polysulfides
- 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
- C10M135/20—Thiols; Sulfides; Polysulfides
- C10M135/22—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M135/26—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl 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
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/06—Perfluorinated 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
- C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2213/02—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen and halogen 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
- C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2213/06—Perfluoro polymers
- C10M2213/062—Polytetrafluoroethylene [PTFE]
- 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
- 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
- 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
- C10M2219/084—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
- 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
- C10N2040/20—Metal working
- C10N2040/24—Metal working without essential removal of material, e.g. forming, gorging, drawing, pressing, stamping, rolling or extruding; Punching metal
- 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
- C10N2040/20—Metal working
- C10N2040/241—Manufacturing joint-less pipes
- 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
- C10N2040/20—Metal working
- C10N2040/242—Hot working
- 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
- C10N2040/20—Metal working
- C10N2040/243—Cold working
- 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
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
- 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
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
- C10N2040/245—Soft metals, e.g. aluminum
- 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
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
- C10N2040/246—Iron or steel
- 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
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
- C10N2040/247—Stainless steel

Definitions

the present invention relates to the use of thioethers of ⁇ -dicarbonyl or ⁇ -cyanocarbonyl compounds for the finishing of lubricants including metal processing oils.
thioethers of .beta.-dicarbonyl or .beta.-cyanocarbonyl compounds are outstandingly suitable as lubricant additives, in particular as "extreme pressure” and “antiwear” additives, and as activators (boosters) of chlorinated paraffins in metalworking oils.
Certain thioethers are known as lubricant additives from EP-OS 1 217. However, these are ⁇ -substituted epithio compounds and their addition products, which cannot be compared structurally with the thioethers to be used according to the invention.
the present invention accordingly relates to lubricants which, as an additive, are a compound of the formula I. or contain a mixture of such compounds in which RC 1 -C 12 alkyl, unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy or halogen, is C 6 -C 10 aryl or a group -OR 3 , R 2 represents a group -C (O) R 4 or -CN , R3 is C 1 -C 12 alkyl, R 4 R 1 , -NH 2 , -NH (R5), -N (R 5 ) 2 , a group -O - (CH 2 ) n -S (O) m -R 3 , where n is a integer between 1 and 6 and m are zero or 1, or a group -CH -SR, R 5 is C 1 -C 12 alkyl and RR or -CN is.
R 1 , R 3 and R 5 are branched or unbranched alkyl as C 1 -C 12 alkyl, such as, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, ⁇ -methyl pentyl, Hexyl, 2,4-dimethylpentyl, octyl, 6-methylheptyl, decyl, dodecyl.
R 1 and R 5 are preferably C 1 -C 4 alkyl, especially methyl.
R 3 is preferably ethyl, tert-butyl, 1,1,3,3-tetramethylbutyl or 1,1,3,3,5,5-hexamethylhexyl.
R 1 is an unsubstituted C 6 -C 10 aryl, for example naphthyl or especially phenyl.
R 1 is, for example, one, two or three times, preferably once in the o- or in particular in the p-position by methyl, ethyl, n-propyl, isopropyl , n-butyl, tert-butyl substituted phenyl.
R 1 is, for example, one, two or three times, preferably once in the o- or in particular in the p-position by methoxy, ethoxy, n-propyloxy, Isopropyloxy, n-butoxy or tert-butoxy substituted phenyl.
R 1 is, for example, phenyl substituted once, twice or three times, preferably once, in the o- or in particular in the p-position by iodine, bromine or in particular chlorine.
lubricants which contain, as an additive, a compound of the formula I in which R 1 is C 1 -C 4 alkyl, phenyl which is unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 alkox or halogen or a group -OR 3 , R is a group -C (O) R 4 , R3 ae t h y l , tert-butyl, 1,1,3,3-tetramethylbutyl or 1,1,3,3, 5,5-hexamethylhexyl and R 4 is R 1 or a group -O-CH 2 CH 2 -SR 3 , where R 3 has the meaning already given in this preference.
thioethers of the formula I to be used according to the invention are known compounds. If some of them are still new, they can be prepared in analogy to known processes, for example by direct action of SC1 2 on ⁇ -dicarbonyl compounds of the formula
R 1 and R 2 have the meaning given above, for example according to SK Gupta, J.Org.Chem. 39, 1944 (1974) or A. Angeli, F. Magnani, Gazz. 24, 342/364 (1894).
Another reaction is the reaction of metalated (for example with sodium) ⁇ -cyanocarbonyl compounds with SCl 2.
the compounds of formula I act in very small amounts in lubricants, in particular as "extreme pressure” and “antiwear” additives and as activators (boosters) of chlorinated paraffins in metalworking oils.
Mineral and synthetic lubricating oils, and mixtures thereof which contain 0.001 to 5% by weight, based on the lubricant, and preferably 0.2-3% by weight of a compound of the formula I or a mixture of such compounds, have excellent lubricating properties especially in strong reduced wear and tear of the friction partners to be lubricated become clear.
lubricants in question are familiar to the person skilled in the art and e.g. in the "Lubricant Pocket Book” (Hüttig Verlag, Heidelberg, (1974). Mineral oils are particularly suitable. Systems particularly suitable for metal processing ("cutting fluids") are described, for example, in JO Cookson, An introduction to cutting fluids, TRIBOLOGY INTERNATIONAL (February 1977), SS.5-11.
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:
Benzotriazole tetrahydrobenzotriazole, 2-mercaptobenzotriazole, 2,5-dimercaptothiadiazole, salicylidene-propylenediamine, salts of salicylaminoguanidine.
Sebacic acid derivatives quinizarin, propyl gallate.
rust inhibitors are:
N-oleoyl sarcosine N-oleoyl sarcosine, sorbitan mono-oleate, lead naphthenate, dodecenylsuccinic anhydride.
Nitrogen-containing compounds e.g .:
viscosity index improvers examples include:
Polymethacrylates vinyl pyrrolidone / methacrylate copolymers, polybutenes, olefin copolymers, styrene-acrylate copolymers.
pour point depressants examples include:
dispersants / surfactants include: polybutenylsuccinic acid imides, polybutenylphosphonic acid derivatives, basic magnesium, calcium and barium sulfonates and phenolates.
wear protection additives examples include:
Example 2 The procedure is as in Example 1, with the difference that a 150 VG 100 oil without costabilizers is used as the base oil. The results are shown in Table II below.
the wear-inhibiting effect of the lubricant composition according to the invention is determined using a conventional lubricant measuring machine (H. Reichert, Maschinen- und Apparatebau).
a test cylinder 2 cm long and 1 cm in diameter is pressed with a force p against a rotating grinding wheel, which rotates in an oil bath at a constant sliding speed of 1.7 m / sec (900 rpm).
the test criterion is the wear cap that forms as a function of the friction path.
the wheel and test specimen are ultrasonically cleaned in mineral spirits and acetone.
the wheel is then run in four times with pure base oil (friction path 100 m).
the basic formulation consists of a 150VG32 oil as the base oil, 5.0% by weight of a commercially available chlorinated paraffin hydrocarbon with 50% chlorine content, 1.0% by weight of a wear protection additive of the triaryl phosphate type and 0.5% by weight N-oleyl sarcosine (rust Inhibitor), based on the entire oil formulation.

Landscapes

Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Chemistry (AREA)
Lubricants (AREA)

EP82810441A 1981-10-29 1982-10-25 Lubrifiant contenant des thioéthers de composés bêta-dicarbonyles ou bêta cyanocarbonyles Withdrawn EP0079302A2 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH6918/81		1981-10-29
CH691881		1981-10-29

Publications (1)

Publication Number	Publication Date
EP0079302A2 true EP0079302A2 (fr)	1983-05-18

Family

ID=4317087

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP82810441A Withdrawn EP0079302A2 (fr)	1981-10-29	1982-10-25	Lubrifiant contenant des thioéthers de composés bêta-dicarbonyles ou bêta cyanocarbonyles

Country Status (2)

Country	Link
EP (1)	EP0079302A2 (fr)
JP (1)	JPS5883097A (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1988005459A1 (fr) *	1987-01-15	1988-07-28	Bp Chemicals (Additives) Limited	Compositions d'huile lubrifiante contenant des additifs anti-usure/anticorrosion
EP1172430A3 (fr) *	2000-06-29	2002-04-03	Bridgestone Corporation	Composition lubrifiante pour filaments en acier et materiau composite filamentaire en caoutchouc-acier

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2658817B2 (ja) *	1993-09-02	1997-09-30	日本電気株式会社	電子部品のリード
JP7024944B2 (ja)	2016-08-26	2022-02-24	出光興産株式会社	金属加工油組成物、及び金属加工方法

1982
- 1982-10-25 EP EP82810441A patent/EP0079302A2/fr not_active Withdrawn
- 1982-10-29 JP JP57190692A patent/JPS5883097A/ja active Pending

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1988005459A1 (fr) *	1987-01-15	1988-07-28	Bp Chemicals (Additives) Limited	Compositions d'huile lubrifiante contenant des additifs anti-usure/anticorrosion
EP0277715A1 (fr) *	1987-01-15	1988-08-10	Bp Chemicals (Additives) Limited	Compositions lubrifiantes contenant des additifs anti-usure et anticorrosifs
AU609773B2 (en) *	1987-01-15	1991-05-09	Bp Chemicals (Additives) Limited	Lubricating oil compositions containing anti-wear/anti-corrosion additives
EP1172430A3 (fr) *	2000-06-29	2002-04-03	Bridgestone Corporation	Composition lubrifiante pour filaments en acier et materiau composite filamentaire en caoutchouc-acier

Also Published As

Publication number	Publication date
JPS5883097A (ja)	1983-05-18

Legal Events

Date	Code	Title	Description
1983-03-19	PUAI	Public reference made under article 153(3) epc to a published international application that has entered the european phase	Free format text: ORIGINAL CODE: 0009012
1983-05-18	17P	Request for examination filed	Effective date: 19821028
1983-05-18	AK	Designated contracting states	Designated state(s): DE FR GB IT
1984-07-30	STAA	Information on the status of an ep patent application or granted ep patent	Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN
1984-10-03	18W	Application withdrawn	Withdrawal date: 19840630
2007-08-08	RIN1	Information on inventor provided before grant (corrected)	Inventor name: WIRTH, HERMANN O., DR.

Publication	Publication Date	Title
US6046144A (en)	2000-04-04	Combination of phosphate based additives and sulfonate salts for hydraulic fluids and lubricating compositions
US5531911A (en)	1996-07-02	Metal free hydraulic fluid with amine salt
US4701273A (en)	1987-10-20	Lubricant compositions containing antioxidants, amine phosphates and 4- (5-) methyl-1-[di-(2-ethylhexyl) aminomethyl]-benzotriazole
US3966623A (en)	1976-06-29	Corrosion inhibited lube oil compositions
EP0072349B1 (fr)	1987-05-13	Tétrahydroquinoline comme agent anti-oxydant pour lubrifiant
NO171280B (no)	1992-11-09	Smoerefettblanding og fremgangsmaate for fremstilling av denne
DE294458T1 (de)	1989-05-11	Schmiermittelgemisch.
US4217233A (en)	1980-08-12	Epithio compounds as additives for lubricants
EP0000514B1 (fr)	1982-01-13	Esters phénoliques N, N-dioctyliques d'acide dithiocarbamique et lubrifiants stabilisés les contenant
DE2601719C2 (fr)	1988-01-07
JPH04114097A (ja)	1992-04-15	金属を含有しない潤滑油
US4066561A (en)	1978-01-03	Organometallic compounds and compositions thereof with lubricants
DE3852207T2 (de)	1995-05-11	Zweckgebundene Flüssigkeiten.
EP0273868A2 (fr)	1988-07-06	Tétrahydroquinoléines N-substituées comme anti-oxydants pour lubrifiants
EP0079302A2 (fr)	1983-05-18	Lubrifiant contenant des thioéthers de composés bêta-dicarbonyles ou bêta cyanocarbonyles
EP0027776B1 (fr)	1985-05-02	Phénols utilisés comme stabilisants et compositions les contenant
DE2756488C2 (de)	1987-04-23	Dithiophosphate und deren Einsatz in Schmiermitteln
EP0004957A2 (fr)	1979-10-31	Compositions et utilisation des dérivés chlorés de l'acide butyrique comme additifs aux lubrifiants
US4248723A (en)	1981-02-03	Acetal derivatives as extreme pressure additives for lubricants
EP0025774B1 (fr)	1983-06-29	Dithiophosphates, leur préparation et lubrifiants les contenant
EP0097118A2 (fr)	1983-12-28	Liquides antioxydants pour lubrifiants et élastomères
DE69007214T2 (de)	1994-07-14	Butenylaromatische Aminstabilisatoren.
DE2715529C2 (fr)	1990-05-23
US2472318A (en)	1949-06-07	Inhibitor
DE3025277A1 (de)	1981-01-08	Schmiermittelzusaetze