EP0444830A1 - Succinimid-Zusammensetzung - Google Patents
Succinimid-Zusammensetzung Download PDFInfo
- Publication number
- EP0444830A1 EP0444830A1 EP91301434A EP91301434A EP0444830A1 EP 0444830 A1 EP0444830 A1 EP 0444830A1 EP 91301434 A EP91301434 A EP 91301434A EP 91301434 A EP91301434 A EP 91301434A EP 0444830 A1 EP0444830 A1 EP 0444830A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- polyamine
- acylating agent
- copper
- oil
- mole ratio
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 44
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 title description 65
- 229960002317 succinimide Drugs 0.000 title description 31
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 59
- 229920000768 polyamine Polymers 0.000 claims abstract description 44
- 239000010949 copper Substances 0.000 claims abstract description 40
- 229910052802 copper Inorganic materials 0.000 claims abstract description 39
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000002270 dispersing agent Substances 0.000 claims abstract description 31
- 239000010687 lubricating oil Substances 0.000 claims abstract description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 30
- 239000000314 lubricant Substances 0.000 claims abstract description 30
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 19
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 11
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- 239000012141 concentrate Substances 0.000 claims description 35
- -1 copper carboxylate compound Chemical class 0.000 claims description 31
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 31
- 239000000654 additive Substances 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 18
- 230000000996 additive effect Effects 0.000 claims description 18
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 15
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 14
- 150000008064 anhydrides Chemical class 0.000 claims description 13
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 11
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 9
- 239000001530 fumaric acid Substances 0.000 claims description 7
- 229920000098 polyolefin Polymers 0.000 claims description 7
- 229940014800 succinic anhydride Drugs 0.000 claims description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 5
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical class ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 5
- 239000001630 malic acid Substances 0.000 claims description 5
- 235000011090 malic acid Nutrition 0.000 claims description 5
- 229920002367 Polyisobutene Polymers 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims description 4
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 229960001124 trientine Drugs 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- 229920001973 fluoroelastomer Polymers 0.000 abstract description 12
- 230000001590 oxidative effect Effects 0.000 abstract description 4
- 239000003921 oil Substances 0.000 description 23
- 235000019198 oils Nutrition 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 15
- 235000011044 succinic acid Nutrition 0.000 description 14
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 13
- 239000011701 zinc Substances 0.000 description 13
- 229910052725 zinc Inorganic materials 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000005749 Copper compound Substances 0.000 description 9
- 150000001880 copper compounds Chemical class 0.000 description 9
- 239000002480 mineral oil Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 235000010446 mineral oil Nutrition 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000001384 succinic acid Substances 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000001991 dicarboxylic acids Chemical class 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 5
- 230000000875 corresponding effect Effects 0.000 description 5
- 239000003599 detergent Substances 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 150000003444 succinic acids Chemical class 0.000 description 5
- 239000010689 synthetic lubricating oil Substances 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 4
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 101150017210 ccmC gene Proteins 0.000 description 3
- 150000001879 copper Chemical class 0.000 description 3
- 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 3
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 239000003879 lubricant additive Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000010688 mineral lubricating oil Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000002530 phenolic antioxidant Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229920013639 polyalphaolefin Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 3
- 239000011369 resultant mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920002449 FKM Polymers 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- BQVVSSAWECGTRN-UHFFFAOYSA-L copper;dithiocyanate Chemical compound [Cu+2].[S-]C#N.[S-]C#N BQVVSSAWECGTRN-UHFFFAOYSA-L 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000012990 dithiocarbamate Substances 0.000 description 2
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000005608 naphthenic acid group Chemical group 0.000 description 2
- 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 2
- 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 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- PFNFFQXMRSDOHW-UHFFFAOYSA-N spermine Chemical compound NCCCNCCCCNCCCN PFNFFQXMRSDOHW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000003860 storage Methods 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- ZQHJVIHCDHJVII-OWOJBTEDSA-N (e)-2-chlorobut-2-enedioic acid Chemical compound OC(=O)\C=C(\Cl)C(O)=O ZQHJVIHCDHJVII-OWOJBTEDSA-N 0.000 description 1
- SASYHUDIOGGZCN-ARJAWSKDSA-N (z)-2-ethylbut-2-enedioic acid Chemical compound CC\C(C(O)=O)=C\C(O)=O SASYHUDIOGGZCN-ARJAWSKDSA-N 0.000 description 1
- FLAQPUNKKBKPDE-FPLPWBNLSA-N (z)-2-hexylbut-2-enedioic acid Chemical compound CCCCCC\C(C(O)=O)=C\C(O)=O FLAQPUNKKBKPDE-FPLPWBNLSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
- MFGALGYVFGDXIX-UHFFFAOYSA-N 2,3-Dimethylmaleic anhydride Chemical compound CC1=C(C)C(=O)OC1=O MFGALGYVFGDXIX-UHFFFAOYSA-N 0.000 description 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- WYSMQSIDRZXTBU-QURGRASLSA-N 3-[(e)-docos-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCCCCCCCCCCCC\C=C\C1CC(=O)OC1=O WYSMQSIDRZXTBU-QURGRASLSA-N 0.000 description 1
- MHALQPUFCVTXKV-AATRIKPKSA-N 3-[(e)-hex-1-enyl]oxolane-2,5-dione Chemical compound CCCC\C=C\C1CC(=O)OC1=O MHALQPUFCVTXKV-AATRIKPKSA-N 0.000 description 1
- NSJAWXMCLJVBPM-UHFFFAOYSA-N 3-butyloxolane-2,5-dione Chemical compound CCCCC1CC(=O)OC1=O NSJAWXMCLJVBPM-UHFFFAOYSA-N 0.000 description 1
- AXGOOCLYBPQWNG-UHFFFAOYSA-N 3-ethylfuran-2,5-dione Chemical compound CCC1=CC(=O)OC1=O AXGOOCLYBPQWNG-UHFFFAOYSA-N 0.000 description 1
- GQNPFQQRWMSYAC-UHFFFAOYSA-N 3-icos-19-enyloxolane-2,5-dione Chemical compound C=CCCCCCCCCCCCCCCCCCCC1CC(=O)OC1=O GQNPFQQRWMSYAC-UHFFFAOYSA-N 0.000 description 1
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- KAYAKFYASWYOEB-UHFFFAOYSA-N 3-octadec-1-enyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCCCCCC=CC1CC(=O)OC1=O KAYAKFYASWYOEB-UHFFFAOYSA-N 0.000 description 1
- MDWVSAYEQPLWMX-UHFFFAOYSA-N 4,4'-Methylenebis(2,6-di-tert-butylphenol) Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 MDWVSAYEQPLWMX-UHFFFAOYSA-N 0.000 description 1
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical class [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- 239000005711 Benzoic acid Substances 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
- CKVAZOXNZDFHND-UHFFFAOYSA-N C(CCCCCCC)OC(CC(=O)C)=O.[Cu] Chemical compound C(CCCCCCC)OC(CC(=O)C)=O.[Cu] CKVAZOXNZDFHND-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920000089 Cyclic olefin copolymer Chemical class 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000005069 Extreme pressure additive Substances 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical class CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 229920000305 Nylon 6,10 Polymers 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 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
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Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
- C10M141/10—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 phosphorus-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
- 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
- C10M141/06—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 nitrogen-containing compound
-
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- 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
- C10M163/00—Lubricating compositions characterised by the additive being a mixture of a compound of unknown or incompletely defined constitution and a non-macromolecular compound, each of these compounds being essential
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/06—Well-defined aromatic compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/026—Butene
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/06—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing conjugated dienes
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/027—Neutral salts thereof
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- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
- F02B1/00—Engines characterised by fuel-air mixture compression
- F02B1/02—Engines characterised by fuel-air mixture compression with positive ignition
- F02B1/04—Engines characterised by fuel-air mixture compression with positive ignition with fuel-air mixture admission into cylinder
Definitions
- the arylene group When R' is arylene, the arylene group will generally contain from 6 to 20 carbon atoms, e.g., phenylene, naphthylene, and the like.
- the arylene groups may be alkyl substituted by from 1 to 14 carbon atoms. Exemplary of such alkarylene groups are -Ar(CH3)-, -Ar(C2H5)-, -Ar(CH3)2-, -Ar(CH3)3-, and the like, wherein "Ar” is a benzene ring.
- R' is aralkylene
- the alkylene groups as described above can be substituted by one or more (e.g., 1-3) aryl groups, e.g., phenyl, tolyl, etc.
- Illustrative oil-soluble copper compounds which may be used in accordance with this invention include cuprous diphenyl dithiophosphate, cuprous di-sechexyl dithiophosphate, cuprous di-isooctyldithiophosphate, cupric naphthenate, cupric oleate, cupric dithiocarbamate, cupric diethyldithiocarbamate, cupric dibutyldithiocarbamate, cupric dioctyldithiocarbamate, lactone oxazoline complexed with copper thiocyanate, bis-oxazoline complexed with copper thiocyanate, bis-oxazoline complexed with copper acetate, copper acetylacetonate, copper octylacetoacetate, and the like.
- the copper-containing antioxidant is employed in the lubricating oil compositions in amounts in the range of 40 to 500, and preferably in the range of 60 to 300, and most preferably, in the range of 100 to 200 parts by weight of copper, per million parts by weight of the lubricant.
- the acyclic hydrocarbyl substituted succinic acylating agents include the hydrocarbylsubstituted succinic acids, the hydrocarbyl-substituted succinic anhydrides, the hydrocarbyl-substituted succinic acid halides (especially the acid fluorides and acid chlorides), and the esters of the hydrocarbyl-substituted succinic acids and lower alcohols (e.g., those containing up to 7 carbon atoms), etc., that is, hydrocarbyl-substituted compounds which can function as carboxylic acylating agents.
- the preferred polyamines used in the practice of this invention are the alkylene polyamines represented by the formula H2N(CH2) n (NH(CH2) n ) m NH2 wherein n is 2 to 10 (preferably 2 to 4, more preferably 2 to 3, and most preferably 2) and m is 0 to 10, (preferably 1 to 6).
- Illustrative are ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, spermine, pentaethylene hexamine, propylene diamine (1,3-propanediamine), butylene diamine (1,4-butanediamine), hexamethylene diamine (1,6-hexanediamine), decamethylene diamine (1,10-decanediamine), and the like.
- Preferred for use is tetraethylene pentamine or a mixture of ethylene polyamines which approximates tetraethylene pentamine such as "DOW E-100" (a commercial mixture available from Dow Chemical Company, Midland, Michigan).
- the acylating agent utilized in step (ii) above is (1) one or a mixture of vicinal dicarboxylic acids containing from 4 to 30 (preferably 4 to 10) carbon atoms in the molecule and characterized in that the two carboxyl groups are separated from each other by two aliphatic carbon atoms, or (2) one or a mixture of anhydrides, acid halides, or esters of such dicarboxylic acids, or (3) any combination of (1) and (2).
- suitable acylating agents for use in step (ii) are:
- Such acylating agent thus encompasses such compounds as maleic anhydride, maleic acid, fumaric acid, malic acid, thiomalic acid, tartaric acid, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, mesaconic acid, chloromaleic acid, ethylmaleic anhydride, dimethylmaleic anhydride, ethylmaleic acid, dimethylmaleic acid, hexylmaleic acid, succinic acid, succinic anhydride, butylsuccinic anhydride, octenylsuccinic anhydride, hexenylsuccinic anhydride, octadecenylsuccinic anhydride, eicosenylsuccinic anhydride, docosenylsuccinic anhydride, etc., and the corresponding acid halides, or esters which are preferably esters of lower alcohols.
- the succinimide dispersants utilized pursuant to this invention are prepared by a process which comprises (i) reacting at least one polyamine with at least one oil soluble acyclic hydrocarbyl substituted succinic acylating agent in which such acyclic hydrocarbyl substituent contains an average of at least 40 carbon atoms, such reaction being conducted using proportions such that the acylating agent is reacted with the polyamine in a mole ratio of from 1.05 to 2.85 moles per mole of polyamine, and (ii) reacting the product so formed with (a) at least one vicinal dicarboxylic acid acylating agent containing 4 to 30 carbon atoms in the molecule and in which the two carboxyl groups are separated from each other by two aliphatic carbon atoms, or (b) an anhydride, acid halide, or ester of at least one such dicarboxylic acid acylating agent, or (c) a combination of (a) and (b), using in the reaction of
- the additive concentrates of this invention will generally contain a suitable diluent or solvent such as a natural or synthetic lubricating oil of appropriate viscosity, together with the above-described oil-soluble copper-containing antioxidant and the above-described succinimide dispersant.
- a suitable diluent or solvent such as a natural or synthetic lubricating oil of appropriate viscosity
- the concentrate will contain the copper-containing antioxidant or mixture of copper-containing antioxidants and the succinimide or mixture of succinimide dispersants in relative amounts such that there is 0.0001 to 0.5, preferably from 0.0004 to 0.1, and most preferably from 0.001 to 0.01 part by weight of copper per part by weight of the succinimide dispersant(s).
- departures from these ranges are permissible and are within the scope of this invention whenever such departures are deemed necessary or appropriate under any given set of circumstances.
- Natural oils including vegetable oils such as rapeseed oil can also be used either alone or in combination with other lubricant types.
- the term lubricating oil for this disclosure includes all the foregoing.
- the succinimide dispersant may be conveniently dispersed as a concentrate of 10 to 80 weight percent of mineral oil, e.g., Solvent 100 Neutral oil with or without other additives being present, and such concentrates are a further embodiment of this invention.
- Finished lubricating oil compositions and additive concentrates of this invention are prepared containing the oil-soluble copper-containing antioxidant and a succinimide dispersant produced as described above, together with conventional amounts of one or more other additives to provide their normal attendant functions.
- conventional additives as viscosity index improvers, dispersant viscosity index improvers, rust inhibitors, metal detergent additives, antiwear additives, extreme pressure additives, and the like.
- additional antioxidants such as phenolic antioxidants, amine antioxidants, etc., can be utilized in the compositions of this invention.
- additional additives that can be used in forming finished lubricants or finished additive concentrates of this invention are such substances as the zinc dialkyl (C3-C8) dithiophosphate wear inhibitors, generally present in amounts of about 0.5 to 5 weight percent.
- Useful detergents include the oil-soluble normal basic or over-based metal, e.g., calcium, magnesium, barium, etc., salts of petroleum naphthenic acids, petroleum sulfonic acids, alkyl benzene sulfonic acids, oil-soluble fatty acids, alkyl salicylic acids, sulfurized or unsulfurized alkyl phenates, and hydrolyzed or unhydrolyzed phosphosulfurized polyolefins.
- Viscosity index improvers include hydrocarbon polymers grafted with, for example, nitrogen-containing monomers, olefin polymers such as polybutene, ethylene-propylene copolymers, hydrogenated polymers and copolymers and terpolymers of styrene with isoprene and/or butadiene, polymers of alkyl acrylates or alkyl methacrylates, copolymers of alkyl methacrylates with N-vinyl pyrrolidone or dimethylamino-alkyl methacrylate, post-grafted polymers of ethylene-propylene with an active monomer such as maleic anhydride which may be further reacted with an alcohol or an alkylene polyamine, styrene/maleic anhydride polymers post-treated with alcohols and amines, etc.
- Antiwear activity can be provided by about 0.01 to 2 weight percent of the aforementioned metal dihydrocarbyl dithiophosphates and the corresponding precursor esters, phosphosulfurized pinenes, sulfurized olefins and hydrocarbons, sulfurized fatty esters and alkyl polysulfides.
- Preferred are the zinc dihydrocarbyl dithiophosphates which are salts of dihydrocarbyl esters of dithiophosphoric acids.
- additives include effective amounts of friction modifiers or fuel economy additives such as the alkyl phosphonates as disclosed in U.S. 4,356,097, aliphatic hydrocarbyl substituted succinimides as disclosed in EPO 0020037, dimer acid esters, as disclosed in U.S. 4,105,571, oleamide, etc., which are present in the oil in amounts of 0.1 to 5 weight percent.
- fuel economy additives such as the alkyl phosphonates as disclosed in U.S. 4,356,097, aliphatic hydrocarbyl substituted succinimides as disclosed in EPO 0020037, dimer acid esters, as disclosed in U.S. 4,105,571, oleamide, etc.
- Glycerol oleates are another example of fuel economy additives and these are usually present in very small amounts, such as 0.05 to 0.2 weight percent based on the weight of the formulated oil.
- maleic anhydride (MA) is added to the first stage reaction product in amount equivalent to 1.25 moles per mole of TEPA used in the first stage and the resultant mixture is heated at 165-170°C for 1.5 hours.
- the succinimide is thus formed using a total mole ratio of anhydrides to TEPA of 3.05:1.
- the mole ratio of PIBSA:MA in this synthesis is 1.44:1.
- the reaction product is suitably diluted with 100 solvent neutral mineral oil such that the nitrogen content of the blend is about 1.8%.
- Example 2 The same general procedure as in Example 1 is employed except that the PIBSA:TEPA mole ratio in the first stage is 2.3:1 and that in the second stage the MA is used in amount equivalent to a mole ratio of 1:1 relative to the TEPA used in the first stage.
- the total mole ratio of anhydrides to polyamine is thus 3.3:1, and the mole ratio of PIBSA:MA is 2.3:1.
- Example 1 The procedure of Example 1 is repeated except that in the first stage the PIBSA and TEPA are reacted in a mole ratio of 2.05:1 and in the second stage the MA is used in amount equivalent to a mole ratio of 2:1 relative to the TEPA used in the first stage.
- the total mole ratio of anhydrides to polyamine is 4.05:1
- the PIBSA:MA mole ratio is 1.03:1.
- maleic acid is added to the first stage reaction product in amount equivalent to one mole per mole of TEPA used in the first stage and the resultant mixture is heated at 165-170°C for 1.5 hours.
- the succinimide is thus formed using a total mole ratio of acylating agents to TEPA of 3.05:1, and the mole ratio of PIBSA to maleic acid is 2.05:1.
- the reaction product is suitably diluted with mineral oil base stock to provide a handleable concentrate.
- Example 6 The procedure of Example 6 is repeated except that fumaric acid is used in the second stage in amount equivalent to a mole ratio of 1:1 relative to the TEPA used in the first stage.
- the total mole ratio of acylating agents to polyamine is 3.05:1
- the mole ratio of PIBSA to fumaric acid is 2.05:1.
- Example 7 The procedure of Example 7 is repeated using an equivalent amount of malic acid in lieu of fumaric acid in the second stage.
- the total mole ratio of acylating agents to polyamine is 3.05:1
- the mole ratio of PIBSA to malic acid is 2.05:1.
- Example 8 The procedure of Example 8 is repeated using in the second stage an equivalent amount of succinic acid in lieu of malic acid.
- the total mole ratio of of acylating agents to polyamine is 3.05:1, and the mole ratio of PIBSA to succinic acid is 2.05:1.
- PIBSA is reacted with TEPA in the first stage in a mole ratio of 2.3:1.
- maleic anhydride is reacted using 0.75 mole per mole of TEPA used in the first stage.
- the product thus is formed with a total mole ratio of acylating agents to TEPA of 3.05:1.
- the mole ratio of PIBSA to MA is 3.07:1.
- Example 15 To individual portions of the respective additive concentrates of Example 15 are added the following components such that the finished concentrates contain 5.5, 17.6, and 27.5% of overbased sulfonates; 1.7, 10.2, and 21.25% of zinc dialkyl dithiophosphate; and/or 0.002, 0.006, and 0.02% of antifoam agent.
- Example 15 The additive concentrates of Example 15 are blended with mineral lubricating oil base stocks and synthetic lubricating oil base stocks such as diester oils and hydrogenated poly- ⁇ -olefin lubricants in amounts such that the copper content of the finished lubricant is in one instance 40 ppm, in another instance 80 ppm, in still another instance 100 ppm, in yet another instance 140 ppm, in a further instance 160 ppm, in yet a further instance 200 ppm, and in a still further instance 300 ppm.
- Viscosity index improver is included in the base oils in amounts between 0.5 and 5% to achieve desired viscosity specifications.
- Example 17 The procedure of Example 17 is repeated using the finished additive concentrates of Example 16.
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- Lubricants (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US48490290A | 1990-02-26 | 1990-02-26 | |
US484902 | 1990-02-26 |
Publications (1)
Publication Number | Publication Date |
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EP0444830A1 true EP0444830A1 (de) | 1991-09-04 |
Family
ID=23926117
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP91301434A Withdrawn EP0444830A1 (de) | 1990-02-26 | 1991-02-22 | Succinimid-Zusammensetzung |
Country Status (1)
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EP (1) | EP0444830A1 (de) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0532264A2 (de) * | 1991-09-09 | 1993-03-17 | Betz Europe, Inc. | Thermische Behandlung eines flüssigen Kohlenwasserstoffmaterials |
GB2288815A (en) * | 1994-04-08 | 1995-11-01 | Exxon Chemical Patents Inc | Lubricating oil anti-wear additives |
US5466387A (en) * | 1993-06-16 | 1995-11-14 | Agip Petroli S.P.A. | Oil-soluble adducts of disuccinimides and anhydrides of unsaturated bicarboxylic aliphatic acids |
WO1995031522A1 (en) * | 1994-05-16 | 1995-11-23 | Exxon Chemical Patents Inc. | Lubricating compositions |
EP0709447A1 (de) * | 1994-10-25 | 1996-05-01 | Exxon Research And Engineering Company | Polycyclische aromatische Verbindungen für verbessertes Niederschlagskontroll |
WO1996012779A1 (en) * | 1994-10-25 | 1996-05-02 | Exxon Research And Engineering Company | Novel cobalt containing deposit control additives |
EP1195427A2 (de) * | 2000-09-28 | 2002-04-10 | Nippon Mitsubishi Oil Corporation | Schmiermittelzusammensetzungen verwendbar als Motoröle |
JP2008260946A (ja) * | 1996-10-29 | 2008-10-30 | Idemitsu Kosan Co Ltd | 新規なコハク酸イミド化合物とその製造方法及び該化合物を含有した潤滑油添加剤、並びに該化合物を配合したディーゼルエンジン用潤滑油組成物 |
WO2015021135A1 (en) * | 2013-08-09 | 2015-02-12 | The Lubrizol Corporation | Reduced engine deposits from dispersant treated with copper |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2056482A (en) * | 1979-08-13 | 1981-03-18 | Exxon Research Engineering Co | Lubricating oil compositions |
EP0072645A2 (de) * | 1981-08-17 | 1983-02-23 | Exxon Research And Engineering Company | Verbessertes Bernsteinsäureimide-Dispergiermittel für Schmieröl |
US4505718A (en) * | 1981-01-22 | 1985-03-19 | The Lubrizol Corporation | Organo transition metal salt/ashless detergent-dispersant combinations |
EP0277729A1 (de) * | 1987-01-21 | 1988-08-10 | Ethyl Corporation | Veschleissschutz-Schmiermittelzusammensetzungen mit geringem Phosphorgehalt |
EP0280580A2 (de) * | 1987-02-27 | 1988-08-31 | Exxon Chemical Patents Inc. | Phosphorarme Schmiermittel |
EP0294045A2 (de) * | 1987-05-11 | 1988-12-07 | Exxon Chemical Patents Inc. | Amin-Mischungshilfsmittel in Schmierölgemischen |
EP0309105A1 (de) * | 1987-09-16 | 1989-03-29 | Exxon Chemical Patents Inc. | Ölige Additivzusammensetzung zur verbesserten Rostverhinderung |
EP0331397A2 (de) * | 1988-02-29 | 1989-09-06 | Exxon Chemical Patents Inc. | In öligen Zubereitungen verwendbare öllösliche Dispersant-Additive |
-
1991
- 1991-02-22 EP EP91301434A patent/EP0444830A1/de not_active Withdrawn
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2056482A (en) * | 1979-08-13 | 1981-03-18 | Exxon Research Engineering Co | Lubricating oil compositions |
US4505718A (en) * | 1981-01-22 | 1985-03-19 | The Lubrizol Corporation | Organo transition metal salt/ashless detergent-dispersant combinations |
EP0072645A2 (de) * | 1981-08-17 | 1983-02-23 | Exxon Research And Engineering Company | Verbessertes Bernsteinsäureimide-Dispergiermittel für Schmieröl |
EP0277729A1 (de) * | 1987-01-21 | 1988-08-10 | Ethyl Corporation | Veschleissschutz-Schmiermittelzusammensetzungen mit geringem Phosphorgehalt |
EP0280580A2 (de) * | 1987-02-27 | 1988-08-31 | Exxon Chemical Patents Inc. | Phosphorarme Schmiermittel |
EP0294045A2 (de) * | 1987-05-11 | 1988-12-07 | Exxon Chemical Patents Inc. | Amin-Mischungshilfsmittel in Schmierölgemischen |
EP0309105A1 (de) * | 1987-09-16 | 1989-03-29 | Exxon Chemical Patents Inc. | Ölige Additivzusammensetzung zur verbesserten Rostverhinderung |
EP0331397A2 (de) * | 1988-02-29 | 1989-09-06 | Exxon Chemical Patents Inc. | In öligen Zubereitungen verwendbare öllösliche Dispersant-Additive |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0532264A2 (de) * | 1991-09-09 | 1993-03-17 | Betz Europe, Inc. | Thermische Behandlung eines flüssigen Kohlenwasserstoffmaterials |
EP0532264A3 (en) * | 1991-09-09 | 1993-07-21 | Betz Europe, Inc. | Heat processing of liquid hydrocarbonaceous medium |
US5466387A (en) * | 1993-06-16 | 1995-11-14 | Agip Petroli S.P.A. | Oil-soluble adducts of disuccinimides and anhydrides of unsaturated bicarboxylic aliphatic acids |
GB2288815A (en) * | 1994-04-08 | 1995-11-01 | Exxon Chemical Patents Inc | Lubricating oil anti-wear additives |
WO1995031522A1 (en) * | 1994-05-16 | 1995-11-23 | Exxon Chemical Patents Inc. | Lubricating compositions |
US5731273A (en) * | 1994-05-16 | 1998-03-24 | Exxon Chemical Patents Inc. | Lubricating compositions |
WO1996012779A1 (en) * | 1994-10-25 | 1996-05-02 | Exxon Research And Engineering Company | Novel cobalt containing deposit control additives |
EP0709447A1 (de) * | 1994-10-25 | 1996-05-01 | Exxon Research And Engineering Company | Polycyclische aromatische Verbindungen für verbessertes Niederschlagskontroll |
JP2008260946A (ja) * | 1996-10-29 | 2008-10-30 | Idemitsu Kosan Co Ltd | 新規なコハク酸イミド化合物とその製造方法及び該化合物を含有した潤滑油添加剤、並びに該化合物を配合したディーゼルエンジン用潤滑油組成物 |
EP0839840B2 (de) † | 1996-10-29 | 2016-01-20 | Idemitsu Kosan Company Limited | Schmierölzusatz enthaltend Bernsteinsäureimid-Verbindung und dessen Verwendung für Dieselmotoren |
EP1195427A2 (de) * | 2000-09-28 | 2002-04-10 | Nippon Mitsubishi Oil Corporation | Schmiermittelzusammensetzungen verwendbar als Motoröle |
EP1195427A3 (de) * | 2000-09-28 | 2003-04-09 | Nippon Mitsubishi Oil Corporation | Schmiermittelzusammensetzungen verwendbar als Motoröle |
WO2015021135A1 (en) * | 2013-08-09 | 2015-02-12 | The Lubrizol Corporation | Reduced engine deposits from dispersant treated with copper |
CN105637073A (zh) * | 2013-08-09 | 2016-06-01 | 路博润公司 | 由用铜处理的分散剂而减少的发动机沉积物 |
US20160298052A1 (en) * | 2013-08-09 | 2016-10-13 | The Lubrizol Corporation | Reduced engine deposits from dispersant treated with copper |
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