US3184412A - Lubricants inhibited against oxidation - Google Patents
Lubricants inhibited against oxidation Download PDFInfo
- Publication number
- US3184412A US3184412A US227037A US22703762A US3184412A US 3184412 A US3184412 A US 3184412A US 227037 A US227037 A US 227037A US 22703762 A US22703762 A US 22703762A US 3184412 A US3184412 A US 3184412A
- Authority
- US
- United States
- Prior art keywords
- acid
- carbon atoms
- radical
- lubricating oil
- piperazine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 230000003647 oxidation Effects 0.000 title description 8
- 238000007254 oxidation reaction Methods 0.000 title description 8
- 239000000314 lubricant Substances 0.000 title description 3
- 239000010687 lubricating oil Substances 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 18
- 229940014800 succinic anhydride Drugs 0.000 claims description 10
- 239000003921 oil Substances 0.000 claims description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 5
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 4
- 230000001050 lubricating effect Effects 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- -1 alkenyl succinic anhydride Chemical compound 0.000 description 34
- 125000004432 carbon atom Chemical group C* 0.000 description 21
- 239000000047 product Substances 0.000 description 19
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 14
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 150000004885 piperazines Chemical class 0.000 description 8
- 229960002317 succinimide Drugs 0.000 description 7
- 125000002947 alkylene group Chemical group 0.000 description 6
- 239000003599 detergent Substances 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 239000002199 base oil Substances 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- GFEGLPYYGVFJPB-UHFFFAOYSA-N CC1(CCCCC1)SP(O)(O)=S Chemical compound CC1(CCCCC1)SP(O)(O)=S GFEGLPYYGVFJPB-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical class CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 0.000 description 1
- KCLJHKVTILZQIS-UHFFFAOYSA-N C(CCCCCCCC)C1=C(C=CC=C1)CC(CCCC)CC Chemical compound C(CCCCCCCC)C1=C(C=CC=C1)CC(CCCC)CC KCLJHKVTILZQIS-UHFFFAOYSA-N 0.000 description 1
- GTBPDKIKDFFCBC-UHFFFAOYSA-N CC(CCCCC)SP(O)(O)=S Chemical compound CC(CCCCC)SP(O)(O)=S GTBPDKIKDFFCBC-UHFFFAOYSA-N 0.000 description 1
- 101150009724 CYBA gene Proteins 0.000 description 1
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- CZGGKXNYNPJFAX-UHFFFAOYSA-N Dimethyldithiophosphate Chemical compound COP(S)(=S)OC CZGGKXNYNPJFAX-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- SYFIMIPHNTZHIN-UHFFFAOYSA-N bis(2-methylpropoxy)-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CC(C)COP(S)(=S)OCC(C)C SYFIMIPHNTZHIN-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- ZMTWSJBCWBBWLJ-UHFFFAOYSA-N di(pentan-2-yloxy)-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCCC(C)OP(S)(=S)OC(C)CCC ZMTWSJBCWBBWLJ-UHFFFAOYSA-N 0.000 description 1
- SZXCCXFNQHQRGF-UHFFFAOYSA-N di(propan-2-yloxy)-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CC(C)OP(S)(=S)OC(C)C SZXCCXFNQHQRGF-UHFFFAOYSA-N 0.000 description 1
- XPRULOZMJZDZEF-UHFFFAOYSA-N dibutoxy-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCCCOP(S)(=S)OCCCC XPRULOZMJZDZEF-UHFFFAOYSA-N 0.000 description 1
- IWHTZOQGVGHYQT-UHFFFAOYSA-N dicyclohexyloxy-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound C1CCCCC1OP(=S)(S)OC1CCCCC1 IWHTZOQGVGHYQT-UHFFFAOYSA-N 0.000 description 1
- IRDLUHRVLVEUHA-UHFFFAOYSA-N diethyl dithiophosphate Chemical compound CCOP(S)(=S)OCC IRDLUHRVLVEUHA-UHFFFAOYSA-N 0.000 description 1
- SWSCCSILRFOSMS-UHFFFAOYSA-N dihydroxy-(2-methylphenyl)sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CC1=CC=CC=C1SP(O)(O)=S SWSCCSILRFOSMS-UHFFFAOYSA-N 0.000 description 1
- MQHRCVXVEKBXFA-UHFFFAOYSA-N dihydroxy-propan-2-ylsulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CC(C)SP(O)(O)=S MQHRCVXVEKBXFA-UHFFFAOYSA-N 0.000 description 1
- KEZILVZPLVUKQG-UHFFFAOYSA-N dihydroxy-sulfanyl-sulfanylidene-$l^{5}-phosphane;pyrrolidine-2,5-dione Chemical compound OP(O)(S)=S.O=C1CCC(=O)N1 KEZILVZPLVUKQG-UHFFFAOYSA-N 0.000 description 1
- CKSHRDPCFLDKPV-UHFFFAOYSA-N diphenoxy-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1OP(=S)(S)OC1=CC=CC=C1 CKSHRDPCFLDKPV-UHFFFAOYSA-N 0.000 description 1
- ZUNFAOLVHKUWCL-UHFFFAOYSA-N dipropoxy-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCCOP(S)(=S)OCCC ZUNFAOLVHKUWCL-UHFFFAOYSA-N 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- AHMZKMOWTURMQK-UHFFFAOYSA-N hexyl-(4-methylpentan-2-yloxy)-silyloxysilane Chemical compound CCCCCC[SiH](O[SiH3])OC(C)CC(C)C AHMZKMOWTURMQK-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- JZALLXAUNPOCEU-UHFFFAOYSA-N tetradecylbenzene Chemical compound CCCCCCCCCCCCCCC1=CC=CC=C1 JZALLXAUNPOCEU-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
- C10M133/58—Heterocyclic 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
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/10—Thio derivatives
- C10M137/105—Thio derivatives not containing metal
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/02—Well-defined aliphatic 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/02—Well-defined aliphatic compounds
- C10M2203/022—Well-defined aliphatic compounds saturated
-
- 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
- C10M2203/02—Well-defined aliphatic compounds
- C10M2203/024—Well-defined aliphatic compounds unsaturated
-
- 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
- C10M2203/04—Well-defined cycloaliphatic 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/06—Well-defined aromatic 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
- 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
-
- 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
- C10M2205/024—Propene
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- C—CHEMISTRY; METALLURGY
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- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- C10M2229/04—Siloxanes with specific structure
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Definitions
- This invention pertains to lubricating oil compositions having incorporated therein metal-free detergents. These particular detergents are also efiiective as oxidation inhibitors.
- the detergents which are added to crankcase oils to reduce this formation of sludges and varnishes are metal organic compounds, particularly those compounds wherein the metal is linked to an organic group through an oxygen atom.
- these metal-containing organic compounds have some effec- 35 tiveness as detergents for dispersing the precursors of the deposits within the oil itself rather than permitting them to form as deposits on the engine parts, they have the disadvantage of forming ash deposits in the engine. These ash deposits lower engine performance by fouling spark plugs and valves, and contributing to pre-ignition.
- these new additives inhibit the oxidation of lubricating oil compositions and also disperse the undesirable polymeric products which are formed.
- lubricating oil compositions particularly useful for heavy duty service are obtained by incorporating therein a product obtained by reacting an alkenyl succinic anhydride and a piperazine derivative, followed by reaction with a dihydrocarbyl dithiophosphoric acid to form a salt thereof.
- alkenyl succinic anhydrides which are reactants herein are of the formula R-CH-C wherein R is a hydrocarbon radical having from 10 to 200 carbon atoms therein, preferably 50 to 200 carbon atoms.
- alkenyl radicals include n-decenyl,
- n-hexadecenyl propylene tetramer
- butylene trimer porpylene polymers containing from 50 to 200 carbon atoms
- polymers of mixtures of l-butene and isobutene having from 50 to 200 carbon atoms are examples of polymers of polymers of polymers of mixtures of l-butene and isobutene having from 50 to 200 carbon atoms.
- piperazine derivatives which contribute the imide and the basic nitrogen atoms of the recation products herein, are represented by the formula era-0H,
- R represents a divalent alkylene radical having from 1 to 3 carbon atoms, and R is hydrogen or an alkyl radical having 1 to 3 carbon atoms.
- R is exemplified by the methylene radical, the ethylene radical, and the propylene radical.
- R is exemplified by hydrogen, the methyl radical, the ethyl radical, the n-propyl radical, the isopropyl radical, etc.
- the dihydroearbyl dithiophosphoric acids which are used in the salt formation herein are represented by the formula wherein R and R represent hydrocarbon radicals each having from 1 to carbon atoms, preferably from 4 to 20 carbon atoms.
- the R nd R combined can have a total of from 6 to 50 carbon atoms, preferably from 10 to carbon atoms.
- R and R radicals are exemplified as follows: methyl, ethyl, propyl, isopropyl, etc.
- dihydrocarbyl dithiophosphoric acid examples include dimethyldithiophosphoric acid, methylethyldithiophosphoric acid, diethyldithiophosphoric acid, di-n-propyl dithiophosphoric acid, di-isopropyldithiophosphoric acid, di-n-butyldithiophosphoric acid, diisobutyldithiophosphoric acid, n-butyl-n-amyldithiophosphoric acid, disec amyldithiophosphoric acid, methyl-n-hexyldithiophosphoric acid, isobutyl-n-hexyldithiophosphoric acid, di-noctyldithiophosphoric acid, methylcyclohexyl dithiophosphoric acid, methylcyclohexyldithiophosphoric acid, dicyclohexyldithiophosphoric acid, methylphenyldithiophosphoric acid, dipheny
- the reaction between a piperazine derivative and an alkenyl succinic anhydride can proceed at temperatures ranging from 220 F. to 500 F., preferably from 220 F. to 350 F.
- the mol ratio of piperazine derivatives to succinic anhydride can vary from 0.5 :1 to 1:1.
- the polyamine-anhydride mol ratio is 0.95:1.
- succinimide the product obtained by the reaction of the piperazine derivative and an alkenyl succinic anhydride will be termed a succinimide.
- the succinimides herein are reacted with a dihydrocarbyl dithiophosphoric acid at temperatures insufiicient for hydrogen sulfide formation; such temperatures being from F. to 220 F., preferably F. to 200 F.
- the mol ratio of the succinimide to the dihydrocarbyl dithiophosphoric acid can vary from 1:1 to 1:4. Preferably, the mol ratio is 1:1.
- salt means the product obtained by reacting the above-identified succinimide with the described dihydrocarbyl dithiophosphoric acid.
- Lubricating oils which can be used as base oils include a wide variety of lubricating oils, such as naphthenic base, paraflin base, and mixed base lubricating oils, other hydrocarbon lubricants, e.g., lubricating oils derived from coal products, and synthetic oils, e.g., alkylene polymers (such as polymers of propylene, butylene, etc., and the mixtures thereof), alkylene oxide-type polymers (e.g., propylene oxide polymers) and derivatives, including alkylene oxide polymers prepared by polymerizing the alkylene oxide in the presence of water or alcohols, e.g., ethyl alcohol, dicarboxylic acid esters (such as those which are prepared by esterifying such dicarboxylic acids as adipic acid, azelaic acid, suberic acid, sebacic acid, alkanol succinic acid, fumaric acid, maleic acid, etc., with alcohols such as butyl alcohol,
- the above base oils may be used individually or in combinations. thereof, Wherever miscible or wherever made so by the use of mutual solvents.
- the succinimide-dithiophosphoric acid salt can be used in oils of lubricating viscosity in amounts of 0.10% to 40%, by weight, preferably 0.1% to 15%, by weight, more preferably 1% to 10%.
- the lubricating oil compositions herein contain products obtained by (1) reacting a piperazine derivative with an alkenyl succinic anhydride, followed by (2) reacting the product of (1) with a hydrocarbyl dithiophosphoric acid.
- Example II illustrates the reaction of a succinimide and a dithiophosphoric acid.
- EXAMPLE II Reaction product a polybutenyl succinimide of B- aminoethyl piperazine and a dialkylphenyl dithiophosphoric acid
- a mixture of 1140 grams (0.5 mol) of a lubricating oil solution of a polybutenyl succinimide of Z-aminoethyl piperazine and 510 grams (0.5 mol) of a lubricating oil solution of a di(alkylphenyl) dithiophosphoric acid was vigorously stirred on a steam plate for two hours at 180 F. to 200 F., wherein said alkyl radical was a propylene polymer containing 12 to 14 carbon atoms.
- Table I presents data obtained with lubricating oil compositions in the L-38 Strip Corrosion Tests, using lead strips. The numbers represent the weight loss in milligrams.
- the increase in viscosity figures represent the percentage increase in viscosity at 100 F. in the oxidation stability test wherein the oil is heated at 340 F. for 20.
- the second alkyl radical contained 6 carbon atoms.
- a lubricating oil composition comprising a major proportion of an oil of lubricating viscosity and from 0.1% to 40% by weight of a product obtained by (1) reacting an alkenyl succinic anhydride having from to 200 carbon atoms in the alkenyl radical witha piperazine derivative of the formula terra ns wherein R is a divalent radical having from 1 to 3 car bon atoms and R is selected from the group consisting of hydrogen and alkyl radicals having from 1 to 3 carbon atoms, wherein the piperazine-anhydride mol ratio is from 0.5 :1 to 1:1, followed by (2) reacting the product of (1) with a dihydrocarbyl dithiophosphoric acid of the formula wherein R andR are hydrocarbon radicals each having from 4 to 20 carbon atoms and having a combined number of carbon atoms from 10 to 40, wherein the mol ratio of the product of (1) to dithiophosphoric acid is from 1:1 to 1:4, said reaction (1) being carried out by heating at a temperature from about 2
- a lubricating oil composition comprising a major proportion of an oil of lubricating viscosity and from 0.1% to 40% by weight of a product obtained by (1) reacting an alkenyl succinic anhydride having from 50 to 200 carbon atoms in the alkenyl radical with N-(fi-amind ethyl piperazine), wherein the piperazine-anhydride mole ratio is from 0.5:1 to 1:1, followed by (2) reacting the 5 6 product of (1) with a dihydrocarbyl dithiophosphoric References Cited by the Examiner Of the frmula S UNITED STATES PATENTS l 2,809,934 10/57 Alford et a1 25232.7 5 2,973,323 2/61 Millikan et a1.
- reaction (1) being carried out by DANIEL WYMANPrlmary Examiner heating at a temperature from about 220 F. to about ALPHONSO D. SULLIVAN, Examiner. 500 F. and said reaction (2) being carried out by heating at a temperature from about 150 F. to about 200 F. 5
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Description
United States Patent 3,184,412 LUBRICANTS INHIBITED AGAINST OXIDATION Warren Lowe, Berkeley, and Frank A. Stuart, Orinda,
(Ialih, assignors to California Research Corporation, F San Francisco, Calif., a corporation of Delaware No Drawing. Filed Sept. 28, 1962, Ser. No. 227,037 4 Claims. (Cl. 25246.7)
This invention pertains to lubricating oil compositions having incorporated therein metal-free detergents. These particular detergents are also efiiective as oxidation inhibitors.
Present day internal combustion engines operate at high speeds and high compression ratios. when used in the so-called city stop-and-go driving, which includes the greater part of the driving conditions for a large percentage of todays automobiles, the internal combustion engines do not reach the most eflicient operating temperature. Under city driving conditions, large amounts of partial oxidation products are formed, and reach the crankcase of the engine by blowing past the piston rings. Most of the partial oxidation products are oil-insoluble, tending to form deposits on the various operating parts of the engine, such as the pistons, piston rings, etc. For the purpose of preventing the deposition of these products on the various engine parts, it is necessary to incorporate detergents in the lubricating oil compositions, thus keeping these polymeric products dispersed in a condition unfavorable for deposition on metals.
For the most part, the detergents which are added to crankcase oils to reduce this formation of sludges and varnishes are metal organic compounds, particularly those compounds wherein the metal is linked to an organic group through an oxygen atom. Although these metal-containing organic compounds have some effec- 35 tiveness as detergents for dispersing the precursors of the deposits within the oil itself rather than permitting them to form as deposits on the engine parts, they have the disadvantage of forming ash deposits in the engine. These ash deposits lower engine performance by fouling spark plugs and valves, and contributing to pre-ignition.
It is a particular object of this invention to provide lubricating oil composition having incorporated therein metal-free detergents which are also effective as oxidation inhibitors. Thus, these new additives inhibit the oxidation of lubricating oil compositions and also disperse the undesirable polymeric products which are formed.
Therefore, in accordance with this invention, it has been found that lubricating oil compositions particularly useful for heavy duty service are obtained by incorporating therein a product obtained by reacting an alkenyl succinic anhydride and a piperazine derivative, followed by reaction with a dihydrocarbyl dithiophosphoric acid to form a salt thereof.
By the use of lubricating oil compositions containing the salts described herein, diesel and gasoline engine products remain remarkably free of deposits and varnish even under severe operating conditions.
The alkenyl succinic anhydrides which are reactants herein are of the formula R-CH-C wherein R is a hydrocarbon radical having from 10 to 200 carbon atoms therein, preferably 50 to 200 carbon atoms. Examples of alkenyl radicals include n-decenyl,
'ice
n-hexadecenyl, propylene tetramer, butylene trimer, porpylene polymers containing from 50 to 200 carbon atoms, and polymers of mixtures of l-butene and isobutene having from 50 to 200 carbon atoms.
The piperazine derivatives, which contribute the imide and the basic nitrogen atoms of the recation products herein, are represented by the formula era-0H,
NR3 GE -C wherein the R represents a divalent alkylene radical having from 1 to 3 carbon atoms, and R is hydrogen or an alkyl radical having 1 to 3 carbon atoms. R is exemplified by the methylene radical, the ethylene radical, and the propylene radical. R is exemplified by hydrogen, the methyl radical, the ethyl radical, the n-propyl radical, the isopropyl radical, etc.
The dihydroearbyl dithiophosphoric acids which are used in the salt formation herein are represented by the formula wherein R and R represent hydrocarbon radicals each having from 1 to carbon atoms, preferably from 4 to 20 carbon atoms. The R nd R combined can have a total of from 6 to 50 carbon atoms, preferably from 10 to carbon atoms.
The R and R radicals are exemplified as follows: methyl, ethyl, propyl, isopropyl, etc.
Examples of dihydrocarbyl dithiophosphoric acid include dimethyldithiophosphoric acid, methylethyldithiophosphoric acid, diethyldithiophosphoric acid, di-n-propyl dithiophosphoric acid, di-isopropyldithiophosphoric acid, di-n-butyldithiophosphoric acid, diisobutyldithiophosphoric acid, n-butyl-n-amyldithiophosphoric acid, disec amyldithiophosphoric acid, methyl-n-hexyldithiophosphoric acid, isobutyl-n-hexyldithiophosphoric acid, di-noctyldithiophosphoric acid, methylcyclohexyl dithiophosphoric acid, methylcyclohexyldithiophosphoric acid, dicyclohexyldithiophosphoric acid, methylphenyldithiophosphoric acid, diphenyldithiophosphoric acid, di- (amylphenyl) dithiophosphoric acid, di- (hexadecylphenyl)dithiophosphoric acid, etc.
The reaction between a piperazine derivative and an alkenyl succinic anhydride can proceed at temperatures ranging from 220 F. to 500 F., preferably from 220 F. to 350 F.
The mol ratio of piperazine derivatives to succinic anhydride can vary from 0.5 :1 to 1:1. Preferably, the polyamine-anhydride mol ratio is 0.95:1.
For purposes of simplicity, the product obtained by the reaction of the piperazine derivative and an alkenyl succinic anhydride will be termed a succinimide.
The succinimides herein are reacted with a dihydrocarbyl dithiophosphoric acid at temperatures insufiicient for hydrogen sulfide formation; such temperatures being from F. to 220 F., preferably F. to 200 F.
The mol ratio of the succinimide to the dihydrocarbyl dithiophosphoric acid can vary from 1:1 to 1:4. Preferably, the mol ratio is 1:1.
As identified herein, the term salt means the product obtained by reacting the above-identified succinimide with the described dihydrocarbyl dithiophosphoric acid.
Lubricating oils which can be used as base oils include a wide variety of lubricating oils, such as naphthenic base, paraflin base, and mixed base lubricating oils, other hydrocarbon lubricants, e.g., lubricating oils derived from coal products, and synthetic oils, e.g., alkylene polymers (such as polymers of propylene, butylene, etc., and the mixtures thereof), alkylene oxide-type polymers (e.g., propylene oxide polymers) and derivatives, including alkylene oxide polymers prepared by polymerizing the alkylene oxide in the presence of water or alcohols, e.g., ethyl alcohol, dicarboxylic acid esters (such as those which are prepared by esterifying such dicarboxylic acids as adipic acid, azelaic acid, suberic acid, sebacic acid, alkanol succinic acid, fumaric acid, maleic acid, etc., with alcohols such as butyl alcohol, hexyl alcohol, Z-ethylhexyl alcohol, dodecyl alcohol, etc.), liquid esters of acids of phosphorus, alkyl benzenes (e.g., monoalkyl benzene) such as dodecyl benzene, tetradecyl benzene, etc., and dialkyl' benzenes (e.g., n-nonyl 2-ethyl hexyl benzene); polyphenyls (e.g., biphenyls and terphanyls), alkyl biphenyl ethers, compounds of silicon (e.g., tetraethyl silicate, tetraisopropyl silicates, tetra(4- methyl-2-tetraethyl) silicate, hexyl(4-methyl-2-pentoxy) disiloxane, poly(methyl) siloxane, poly(methylphenyl) .siloxane, etc. Synthetic oils of the alkylene oxide-type polymers which may be used include those exemplified by the alkylene oxide polymers.
The above base oils may be used individually or in combinations. thereof, Wherever miscible or wherever made so by the use of mutual solvents.
The succinimide-dithiophosphoric acid salt can be used in oils of lubricating viscosity in amounts of 0.10% to 40%, by weight, preferably 0.1% to 15%, by weight, more preferably 1% to 10%.
Thus, the lubricating oil compositions herein contain products obtained by (1) reacting a piperazine derivative with an alkenyl succinic anhydride, followed by (2) reacting the product of (1) with a hydrocarbyl dithiophosphoric acid.
The reaction of an alkenyl succinimide with a piperazine derivative is illustrated in the following example.
EXAMPLE I Reaction product of N-ethylpiperazine and polybutenyl succinic anhydride A mixture of 18 grams (0.14 mol) of N-(B-aminoethyl) piperazine and 200 grams (0.127 mol) of a polybutenyl succinic anhydride wherein the polybutenyl radical was derived from a polyisobutene having about 66 carbon atoms, was blended with agitation at 125 F. in a nitrogen atmosphere. The temperature was increased to 500 F. during a period of one hour, after which the absolute pressure was reduced to about 200 mm. Hg during a period of 30 minutes to facilitate the removal of water and unreacted piperazine. The reaction mixture was then allowed to reach room temperature at this reduced pressure. The reaction product contained 2.59% by weight of nitrogen.
Example II illustrates the reaction of a succinimide and a dithiophosphoric acid.
EXAMPLE II Reaction product a polybutenyl succinimide of B- aminoethyl piperazine and a dialkylphenyl dithiophosphoric acid A mixture of 1140 grams (0.5 mol) of a lubricating oil solution of a polybutenyl succinimide of Z-aminoethyl piperazine and 510 grams (0.5 mol) of a lubricating oil solution of a di(alkylphenyl) dithiophosphoric acid was vigorously stirred on a steam plate for two hours at 180 F. to 200 F., wherein said alkyl radical was a propylene polymer containing 12 to 14 carbon atoms.
Table I presents data obtained with lubricating oil compositions in the L-38 Strip Corrosion Tests, using lead strips. The numbers represent the weight loss in milligrams.
The increase in viscosity figures represent the percentage increase in viscosity at 100 F. in the oxidation stability test wherein the oil is heated at 340 F. for 20.
bon atoms, and the second alkyl radical contained 6 carbon atoms.
TABLE I L-38 test Viscosity Composition result weight increase,
loss (mgrus) percent 1. Base oil plus 2.1% weight additive A-" 1, 747 640 2. Base oil plus 3.1% weight additive B 22 11 3. Base oil plus 3.1% weight additive O--. 20 3 We claim:
1. A lubricating oil composition comprising a major proportion of an oil of lubricating viscosity and from 0.1% to 40% by weight of a product obtained by (1) reacting an alkenyl succinic anhydride having from to 200 carbon atoms in the alkenyl radical witha piperazine derivative of the formula terra ns wherein R is a divalent radical having from 1 to 3 car bon atoms and R is selected from the group consisting of hydrogen and alkyl radicals having from 1 to 3 carbon atoms, wherein the piperazine-anhydride mol ratio is from 0.5 :1 to 1:1, followed by (2) reacting the product of (1) with a dihydrocarbyl dithiophosphoric acid of the formula wherein R andR are hydrocarbon radicals each having from 4 to 20 carbon atoms and having a combined number of carbon atoms from 10 to 40, wherein the mol ratio of the product of (1) to dithiophosphoric acid is from 1:1 to 1:4, said reaction (1) being carried out by heating at a temperature from about 220 F. to about 500 F., and said reaction (2) being carried out by heating at a temperature from about F. to about 200 F.
2. A lubricating oil composition according to claim 1 in which the dihydrocarbyl dithiophosphoric acid is alkylphenyl dithiophosphoric acid.
3. A lubricating oil composition according to claim 1 in which the dihydrocarbyl' dithiophosphoric acid is dialkyl dithiophosphoric acid.
4. A lubricating oil composition comprising a major proportion of an oil of lubricating viscosity and from 0.1% to 40% by weight of a product obtained by (1) reacting an alkenyl succinic anhydride having from 50 to 200 carbon atoms in the alkenyl radical with N-(fi-amind ethyl piperazine), wherein the piperazine-anhydride mole ratio is from 0.5:1 to 1:1, followed by (2) reacting the 5 6 product of (1) with a dihydrocarbyl dithiophosphoric References Cited by the Examiner Of the frmula S UNITED STATES PATENTS l 2,809,934 10/57 Alford et a1 25232.7 5 2,973,323 2/61 Millikan et a1. 25232.7 I 2,995,568 8/61 MalZ et al. 260326.5 R 3,018,247 1/62 Anderson et a1. 25232.7 wherein R and R are hydrocarbon radicals each having 3024237 3/62 Drummond et a1 25 2 5 from 4 to 20 carbon atoms and having a combined num- 3,058,910 10/62 Culmer 252 32-7 ber of carbon atoms from 10 to 40, wherein the mole 10 3,074,990 1/63 Cyba 252 32'7 ratio of the product of (1) to dithiophosphoric acid is from 1:1 to 1:4, said reaction (1) being carried out by DANIEL WYMANPrlmary Examiner heating at a temperature from about 220 F. to about ALPHONSO D. SULLIVAN, Examiner. 500 F. and said reaction (2) being carried out by heating at a temperature from about 150 F. to about 200 F. 5
Claims (1)
1. A LUBRICATING OIL COMPOSITION COMPRISING A MAJOR PROPORTION OF AN OIL OF LUBRICATING VISCOSITY AND FROM 0.1% TO 40% BY WEIGHT OF A PRODUCT OBTAINED BY (1) REACTING AN ALKENYL SUCCINIC ANHYDRIDE HAVING FROM 50 TO 200 CARBON ATOMS IN THE ALKENYL RADICAL WITH A PIPERAZINE DERIVATIVE OF THE FORMULA
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US227037A US3184412A (en) | 1962-09-28 | 1962-09-28 | Lubricants inhibited against oxidation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US227037A US3184412A (en) | 1962-09-28 | 1962-09-28 | Lubricants inhibited against oxidation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3184412A true US3184412A (en) | 1965-05-18 |
Family
ID=22851486
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US227037A Expired - Lifetime US3184412A (en) | 1962-09-28 | 1962-09-28 | Lubricants inhibited against oxidation |
Country Status (1)
| Country | Link |
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| US (1) | US3184412A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3291817A (en) * | 1963-06-20 | 1966-12-13 | Exxon Research Engineering Co | Polymer coordinated metal compounds |
| US3294684A (en) * | 1963-07-11 | 1966-12-27 | Standard Oil Co | Lubricant compositions containing detergency additives |
| US3294816A (en) * | 1963-12-12 | 1966-12-27 | Universal Oil Prod Co | Acid-amine-phosphate reaction product and use thereof |
| US3324032A (en) * | 1964-12-22 | 1967-06-06 | Exxon Research Engineering Co | Reaction product of dithiophosphoric acid and dibasic acid anhydride |
| US3488285A (en) * | 1967-03-16 | 1970-01-06 | Texaco Inc | Alkenyl succinic acid-aziridinyl phosphine chalcogenide adducts,method of preparation and lubricant compositions thereof |
| US3502677A (en) * | 1963-06-17 | 1970-03-24 | Lubrizol Corp | Nitrogen-containing and phosphorus-containing succinic derivatives |
| US3511780A (en) * | 1966-02-09 | 1970-05-12 | Exxon Research Engineering Co | Oil-soluble ashless dispersant-detergent-inhibitors |
| US3623985A (en) * | 1967-03-29 | 1971-11-30 | Chevron Res | Polysuccinimide ashless detergents as lubricating oil additives |
| WO1985003709A1 (en) * | 1984-02-14 | 1985-08-29 | The Lubrizol Corporation | Nitrogen- and phosphorus-containing compositions and aqueous systems containing same |
| US5472624A (en) * | 1993-10-06 | 1995-12-05 | Institut Francais Du Petrole | Lubricating compositions containing an amine phosphate with a terminal imide ring |
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| US3024237A (en) * | 1959-08-24 | 1962-03-06 | California Research Corp | Alkenyl succinimides of piperazines |
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| US2809934A (en) * | 1953-10-01 | 1957-10-15 | Standard Oil Co | Detergent lubricants and lubricating oil additives and process of making the same |
| US2973323A (en) * | 1956-12-31 | 1961-02-28 | Pure Oil Co | Lubricating oil composition containing heterocyclic polyamine salts of partial ester of phosphorodithioic acid as antiwear agent |
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3502677A (en) * | 1963-06-17 | 1970-03-24 | Lubrizol Corp | Nitrogen-containing and phosphorus-containing succinic derivatives |
| US3291817A (en) * | 1963-06-20 | 1966-12-13 | Exxon Research Engineering Co | Polymer coordinated metal compounds |
| US3294684A (en) * | 1963-07-11 | 1966-12-27 | Standard Oil Co | Lubricant compositions containing detergency additives |
| US3316175A (en) * | 1963-12-12 | 1967-04-25 | Universal Oil Prod Co | Stabilization of organic substances |
| US3294816A (en) * | 1963-12-12 | 1966-12-27 | Universal Oil Prod Co | Acid-amine-phosphate reaction product and use thereof |
| US3324032A (en) * | 1964-12-22 | 1967-06-06 | Exxon Research Engineering Co | Reaction product of dithiophosphoric acid and dibasic acid anhydride |
| US3511780A (en) * | 1966-02-09 | 1970-05-12 | Exxon Research Engineering Co | Oil-soluble ashless dispersant-detergent-inhibitors |
| US3488285A (en) * | 1967-03-16 | 1970-01-06 | Texaco Inc | Alkenyl succinic acid-aziridinyl phosphine chalcogenide adducts,method of preparation and lubricant compositions thereof |
| US3623985A (en) * | 1967-03-29 | 1971-11-30 | Chevron Res | Polysuccinimide ashless detergents as lubricating oil additives |
| WO1985003709A1 (en) * | 1984-02-14 | 1985-08-29 | The Lubrizol Corporation | Nitrogen- and phosphorus-containing compositions and aqueous systems containing same |
| US5041598A (en) * | 1984-02-14 | 1991-08-20 | The Lubrizol Corporation | Nitrogen- and phosphorus-containing compositions and aqueous systems containing same |
| JPH0826340B2 (en) * | 1984-02-14 | 1996-03-13 | ザ▲ルーブリゾル コーポレイション | Compositions containing nitrogen and phosphorus, and aqueous systems containing the compositions |
| US5472624A (en) * | 1993-10-06 | 1995-12-05 | Institut Francais Du Petrole | Lubricating compositions containing an amine phosphate with a terminal imide ring |
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