AU2003253351B2 - Engine oils comprising lead corrosion-inhibitors - Google Patents
Engine oils comprising lead corrosion-inhibitors Download PDFInfo
- Publication number
- AU2003253351B2 AU2003253351B2 AU2003253351A AU2003253351A AU2003253351B2 AU 2003253351 B2 AU2003253351 B2 AU 2003253351B2 AU 2003253351 A AU2003253351 A AU 2003253351A AU 2003253351 A AU2003253351 A AU 2003253351A AU 2003253351 B2 AU2003253351 B2 AU 2003253351B2
- Authority
- AU
- Australia
- Prior art keywords
- triazole
- group
- formula
- tert
- butyl
- 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.)
- Ceased
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- 239000010705 motor oil Substances 0.000 title claims description 37
- 239000003112 inhibitor Substances 0.000 title claims description 8
- -1 isooctylaminomethyl Chemical group 0.000 claims description 52
- 150000003852 triazoles Chemical class 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000000654 additive Substances 0.000 claims description 21
- 238000005260 corrosion Methods 0.000 claims description 18
- 230000007797 corrosion Effects 0.000 claims description 18
- 239000003921 oil Substances 0.000 claims description 17
- 235000019198 oils Nutrition 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 239000003963 antioxidant agent Substances 0.000 claims description 14
- 239000003607 modifier Substances 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 12
- 229910052802 copper Inorganic materials 0.000 claims description 12
- 239000010949 copper Substances 0.000 claims description 12
- 239000007866 anti-wear additive Substances 0.000 claims description 11
- 239000012530 fluid Substances 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 230000000996 additive effect Effects 0.000 claims description 9
- 239000003599 detergent Substances 0.000 claims description 8
- 239000002270 dispersing agent Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 6
- AVBBHCMDRGQBNW-UHFFFAOYSA-N 2-ethyl-n-(2-ethylhexyl)-n-(1,2,4-triazol-1-ylmethyl)hexan-1-amine Chemical compound CCCCC(CC)CN(CC(CC)CCCC)CN1C=NC=N1 AVBBHCMDRGQBNW-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 5
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 5
- 239000008158 vegetable oil Substances 0.000 claims description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
- 239000002518 antifoaming agent Substances 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 claims description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 3
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229950000688 phenothiazine Drugs 0.000 claims description 3
- QAHJJQGHAWTUQU-UHFFFAOYSA-N 5-methyl-2h-triazol-4-amine Chemical compound CC1=NNN=C1N QAHJJQGHAWTUQU-UHFFFAOYSA-N 0.000 claims description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 2
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims 1
- BWIHEPSJBISUIM-UHFFFAOYSA-N N-propan-2-yl-N-(2H-triazol-4-ylmethyl)propan-2-amine Chemical compound C(C)(C)N(C(C)C)CC=1N=NNC=1 BWIHEPSJBISUIM-UHFFFAOYSA-N 0.000 claims 1
- 101100258328 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) crc-2 gene Proteins 0.000 claims 1
- SFONHZXROQHFMH-UHFFFAOYSA-N n,n-dimethyl-1-(2h-triazol-4-yl)methanamine Chemical compound CN(C)CC1=CNN=N1 SFONHZXROQHFMH-UHFFFAOYSA-N 0.000 claims 1
- 239000000306 component Substances 0.000 description 17
- 150000002148 esters Chemical class 0.000 description 13
- 235000006708 antioxidants Nutrition 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 239000008186 active pharmaceutical agent Substances 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical class C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 3
- LRUDIIUSNGCQKF-UHFFFAOYSA-N 5-methyl-1H-benzotriazole Chemical compound C1=C(C)C=CC2=NNN=C21 LRUDIIUSNGCQKF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Natural products CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 239000012964 benzotriazole Substances 0.000 description 3
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002314 glycerols Chemical class 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 239000011733 molybdenum Substances 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical class S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 2
- SLUKQUGVTITNSY-UHFFFAOYSA-N 2,6-di-tert-butyl-4-methoxyphenol Chemical compound COC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SLUKQUGVTITNSY-UHFFFAOYSA-N 0.000 description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 2
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- 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 2
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- 229910019142 PO4 Inorganic materials 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
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- JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetonamine Chemical compound CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
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- 239000003795 chemical substances by application Substances 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
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- 125000000524 functional group Chemical group 0.000 description 2
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- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000006078 metal deactivator Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
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- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
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- 239000000047 product Substances 0.000 description 2
- 239000011732 tocopherol Substances 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- FKFOHTUAFNQANW-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl) octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FKFOHTUAFNQANW-UHFFFAOYSA-N 0.000 description 1
- PPOGXILTOMPFIE-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)carbamic acid Chemical compound CC(C)(C)C1=CC(NC(O)=O)=CC(C(C)(C)C)=C1O PPOGXILTOMPFIE-UHFFFAOYSA-N 0.000 description 1
- ZEBMSMUPGIOANU-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methylphosphonic acid Chemical compound CC(C)(C)C1=CC(CP(O)(O)=O)=CC(C(C)(C)C)=C1O ZEBMSMUPGIOANU-UHFFFAOYSA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
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- BUGAMLAPDQMYNZ-UHFFFAOYSA-N 1-(2,4,4-trimethylpentan-2-yl)-10h-phenothiazine Chemical class S1C2=CC=CC=C2NC2=C1C=CC=C2C(C)(C)CC(C)(C)C BUGAMLAPDQMYNZ-UHFFFAOYSA-N 0.000 description 1
- SQZCAOHYQSOZCE-UHFFFAOYSA-N 1-(diaminomethylidene)-2-(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1N=C(N)N=C(N)N SQZCAOHYQSOZCE-UHFFFAOYSA-N 0.000 description 1
- KSYAJTVGOSTFLK-UHFFFAOYSA-N 1-(nonoxymethyl)benzotriazole Chemical compound C1=CC=C2N(COCCCCCCCCC)N=NC2=C1 KSYAJTVGOSTFLK-UHFFFAOYSA-N 0.000 description 1
- VMDYMJSKWCVEEB-UHFFFAOYSA-N 1-[3,5-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyl]-1,3,5-triazinan-1-yl]-3-(3,5-ditert-butyl-4-hydroxyphenyl)propan-1-one Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)N2CN(CN(C2)C(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 VMDYMJSKWCVEEB-UHFFFAOYSA-N 0.000 description 1
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- PIDRVLYMNGNSPO-UHFFFAOYSA-N 1-methyl-2-[(1-methylimidazol-2-yl)-octoxymethyl]imidazole Chemical compound N=1C=CN(C)C=1C(OCCCCCCCC)C1=NC=CN1C PIDRVLYMNGNSPO-UHFFFAOYSA-N 0.000 description 1
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- JUHXTONDLXIGGK-UHFFFAOYSA-N 1-n,4-n-bis(5-methylheptan-3-yl)benzene-1,4-diamine Chemical compound CCC(C)CC(CC)NC1=CC=C(NC(CC)CC(C)CC)C=C1 JUHXTONDLXIGGK-UHFFFAOYSA-N 0.000 description 1
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- AIMXDOGPMWDCDF-UHFFFAOYSA-N 1-n,4-n-dicyclohexylbenzene-1,4-diamine Chemical compound C1CCCCC1NC(C=C1)=CC=C1NC1CCCCC1 AIMXDOGPMWDCDF-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C10M135/02—Sulfurised compounds
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- C10M2219/066—Thiocarbamic type compounds
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- C10M2219/068—Thiocarbamate metal salts
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- C10M2219/083—Dibenzyl sulfide
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- C10M2219/084—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
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- 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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- C10M2223/045—Metal containing thio derivatives
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- C10M2223/047—Thioderivatives not containing metallic elements
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- C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
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- C10M2227/09—Complexes with metals
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- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40129902P | 2002-08-06 | 2002-08-06 | |
| US60/401,299 | 2002-08-06 | ||
| PCT/EP2003/008352 WO2004015043A1 (en) | 2002-08-06 | 2003-07-29 | Engine oils comprising lead corrosion-inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2003253351A1 AU2003253351A1 (en) | 2004-02-25 |
| AU2003253351B2 true AU2003253351B2 (en) | 2009-07-02 |
Family
ID=31715705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2003253351A Ceased AU2003253351B2 (en) | 2002-08-06 | 2003-07-29 | Engine oils comprising lead corrosion-inhibitors |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20040038835A1 (enExample) |
| EP (1) | EP1532232A1 (enExample) |
| JP (1) | JP2005534782A (enExample) |
| KR (1) | KR20050032104A (enExample) |
| CN (1) | CN1675341A (enExample) |
| AU (1) | AU2003253351B2 (enExample) |
| BR (1) | BR0313248A (enExample) |
| CA (1) | CA2494639A1 (enExample) |
| MX (1) | MXPA05001129A (enExample) |
| TW (1) | TW200413518A (enExample) |
| WO (1) | WO2004015043A1 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7732389B2 (en) * | 2005-02-04 | 2010-06-08 | Exxonmobil Chemical Patents Inc. | Lubricating fluids with low traction characteristics |
| US20060264341A1 (en) * | 2005-05-20 | 2006-11-23 | Culley Scott A | Transmission composition |
| CN100387696C (zh) * | 2005-12-29 | 2008-05-14 | 上海交通大学 | 苯并三氮唑多硫化物极压抗腐蚀添加剂及其制备方法 |
| KR101455406B1 (ko) * | 2006-03-31 | 2014-10-27 | 이데미쓰 고산 가부시키가이샤 | 윤활유 첨가제, 그것을 함유하는 윤활유 조성물, 각종 저마찰 접동 부재, 롤링 베어링 및 슬라이딩 베어링 |
| ES2301358B1 (es) | 2006-05-12 | 2009-06-22 | Repsol Ypf, S.A. | Nueva composicion de combustible estabilizado. |
| JP5395658B2 (ja) * | 2006-05-23 | 2014-01-22 | チバ ホールディング インコーポレーテッド | 非鉄金属用腐食防止組成物 |
| KR20090089851A (ko) * | 2006-11-27 | 2009-08-24 | 시바 홀딩 인코포레이티드 | 안정화된 바이오디젤 연료 조성물 |
| US20080139425A1 (en) * | 2006-12-11 | 2008-06-12 | Hutchison David A | Lubricating composition |
| EP2118245A2 (en) * | 2007-02-07 | 2009-11-18 | Ciba Holding Inc. | Multiple metal corrosion inhibitor |
| US20090042752A1 (en) * | 2007-08-09 | 2009-02-12 | Malcolm Waddoups | Lubricant Compositions with Reduced Phosphorous Content for Engines having Catalytic Converters |
| US20110237479A1 (en) * | 2008-11-05 | 2011-09-29 | The Lubrizol Corporation | Method of Lubricating an Internal Combustion Engine |
| CA2752682A1 (en) | 2009-02-18 | 2010-08-26 | The Lubrizol Corporation | Composition containing ester compounds and a method of lubricating an internal combustion engine |
| EP2398874B1 (en) | 2009-02-18 | 2017-04-26 | The Lubrizol Corporation | Compounds and a method of lubricating an internal combustion engine |
| US8377856B2 (en) | 2009-05-14 | 2013-02-19 | Afton Chemical Corporation | Extended drain diesel lubricant formulations |
| US20100292112A1 (en) * | 2009-05-14 | 2010-11-18 | Afton Chemical Corporation | Extended drain diesel lubricant formulations |
| DE102009033161A1 (de) * | 2009-07-13 | 2011-01-27 | Schülke & Mayr GmbH | Additivgemsich für die bakterizide und Korrosionsschutzausrüstung von Treib- und Brennstoffen |
| US8802606B2 (en) * | 2010-08-06 | 2014-08-12 | Basf Se | Lubricant composition having improved antiwear properties |
| US10190069B2 (en) | 2011-03-10 | 2019-01-29 | The Lubrizol Corporation | Lubricating composition containing a thiocarbamate compound |
| US8236204B1 (en) | 2011-03-11 | 2012-08-07 | Wincom, Inc. | Corrosion inhibitor compositions comprising tetrahydrobenzotriazoles solubilized in activating solvents and methods for using same |
| US8236205B1 (en) | 2011-03-11 | 2012-08-07 | Wincom, Inc. | Corrosion inhibitor compositions comprising tetrahydrobenzotriazoles and other triazoles and methods for using same |
| KR101234275B1 (ko) * | 2011-03-21 | 2013-02-18 | 한국화학연구원 | 트리아졸 함유 숙신산 에스테르 화합물 및 그를 포함하는 방청제 |
| JP5771103B2 (ja) * | 2011-09-16 | 2015-08-26 | 昭和シェル石油株式会社 | 潤滑油組成物 |
| WO2017030783A1 (en) * | 2015-08-14 | 2017-02-23 | Vanderbilt Chemicals, Llc | Novel alkylated diphenylamine derivatives of triazole and lubricating compositions containing the same |
| ES2767353T3 (es) | 2015-08-14 | 2020-06-17 | Vanderbilt Chemicals Llc | Aditivo para composiciones lubricantes que comprende un compuesto de organomolibdeno y un triazol derivatizado |
| CN112424321B (zh) * | 2018-06-08 | 2022-08-23 | 路博润公司 | 蒸气相腐蚀抑制 |
| CN120574619A (zh) | 2020-11-17 | 2025-09-02 | 松原实业有限公司 | 性能提高的包含烷基化二苯胺的组合物 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4734209A (en) * | 1984-04-04 | 1988-03-29 | Ciba-Geigy Corporation | Metal deactivators |
| EP0721979A2 (en) * | 1995-01-13 | 1996-07-17 | Ciba-Geigy Ag | Stabilized lubricant compositions |
| US6410490B1 (en) * | 1999-05-19 | 2002-06-25 | Ciba Specialty Chemicals Corporation | Stabilized hydrotreated and hydrowaxed lubricant compositions |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1111680A (en) * | 1965-12-01 | 1968-05-01 | Shell Int Research | Improvements in or relating to ester-base compositions |
| US4491527A (en) * | 1982-04-26 | 1985-01-01 | The Lubrizol Corporation | Ester-heterocycle compositions useful as "lead paint" inhibitors in lubricants |
| CA2105132A1 (en) * | 1992-09-28 | 1994-03-29 | John W. Frankenfeld | Substituted 1, 2, 4-triazole containing lubricants having improved oxidation stability |
| JP3654371B2 (ja) * | 1995-02-27 | 2005-06-02 | 出光興産株式会社 | ディーゼル軽油組成物 |
| US6207623B1 (en) * | 2000-01-14 | 2001-03-27 | Exxonmobil Research And Engineering Company | Industrial oils of enhanced resistance to oxidation |
-
2003
- 2003-06-19 US US10/465,423 patent/US20040038835A1/en not_active Abandoned
- 2003-07-29 EP EP03784098A patent/EP1532232A1/en not_active Withdrawn
- 2003-07-29 WO PCT/EP2003/008352 patent/WO2004015043A1/en not_active Ceased
- 2003-07-29 AU AU2003253351A patent/AU2003253351B2/en not_active Ceased
- 2003-07-29 MX MXPA05001129A patent/MXPA05001129A/es active IP Right Grant
- 2003-07-29 JP JP2004526808A patent/JP2005534782A/ja active Pending
- 2003-07-29 KR KR1020057001865A patent/KR20050032104A/ko not_active Ceased
- 2003-07-29 BR BR0313248-0A patent/BR0313248A/pt not_active IP Right Cessation
- 2003-07-29 CN CNA038188643A patent/CN1675341A/zh active Pending
- 2003-07-29 CA CA002494639A patent/CA2494639A1/en not_active Abandoned
- 2003-08-04 TW TW092121255A patent/TW200413518A/zh unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4734209A (en) * | 1984-04-04 | 1988-03-29 | Ciba-Geigy Corporation | Metal deactivators |
| EP0721979A2 (en) * | 1995-01-13 | 1996-07-17 | Ciba-Geigy Ag | Stabilized lubricant compositions |
| US5580482A (en) * | 1995-01-13 | 1996-12-03 | Ciba-Geigy Corporation | Stabilized lubricant compositions |
| US6410490B1 (en) * | 1999-05-19 | 2002-06-25 | Ciba Specialty Chemicals Corporation | Stabilized hydrotreated and hydrowaxed lubricant compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA05001129A (es) | 2005-05-16 |
| CN1675341A (zh) | 2005-09-28 |
| CA2494639A1 (en) | 2004-02-19 |
| KR20050032104A (ko) | 2005-04-06 |
| TW200413518A (en) | 2004-08-01 |
| EP1532232A1 (en) | 2005-05-25 |
| BR0313248A (pt) | 2005-07-12 |
| WO2004015043A1 (en) | 2004-02-19 |
| US20040038835A1 (en) | 2004-02-26 |
| AU2003253351A1 (en) | 2004-02-25 |
| JP2005534782A (ja) | 2005-11-17 |
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| PC1 | Assignment before grant (sect. 113) |
Owner name: BASF SE Free format text: FORMER APPLICANT(S): CIBA HOLDING INC. |
|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |