US3185643A - Oxidation resistant lubricants - Google Patents
Oxidation resistant lubricants Download PDFInfo
- Publication number
- US3185643A US3185643A US227036A US22703662A US3185643A US 3185643 A US3185643 A US 3185643A US 227036 A US227036 A US 227036A US 22703662 A US22703662 A US 22703662A US 3185643 A US3185643 A US 3185643A
- Authority
- US
- United States
- Prior art keywords
- acid
- dithiophosphoric acid
- carbon atoms
- lubricating oil
- succinimide
- 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 7
- 238000007254 oxidation reaction Methods 0.000 title description 7
- 239000000314 lubricant Substances 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims description 23
- 239000010687 lubricating oil Substances 0.000 claims description 21
- 229920000768 polyamine Polymers 0.000 claims description 15
- 229920001281 polyalkylene Polymers 0.000 claims description 13
- 229940014800 succinic anhydride Drugs 0.000 claims description 12
- 239000003921 oil Substances 0.000 claims description 9
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 6
- 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 30
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 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 17
- 239000002199 base oil Substances 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 239000000654 additive Substances 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 229960002317 succinimide Drugs 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 10
- 230000000996 additive effect Effects 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 9
- 125000002947 alkylene group Chemical group 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003599 detergent Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- CZGGKXNYNPJFAX-UHFFFAOYSA-N Dimethyldithiophosphate Chemical compound COP(S)(=S)OC CZGGKXNYNPJFAX-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
- 239000004743 Polypropylene Substances 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
- 238000012937 correction Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 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 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000004312 hexamethylene tetramine Substances 0.000 description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 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
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 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
- BZJTUOGZUKFLQT-UHFFFAOYSA-N 1,3,5,7-tetramethylcyclooctane Chemical group CC1CC(C)CC(C)CC(C)C1 BZJTUOGZUKFLQT-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical class CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 0.000 description 1
- AZPVYDDUIKAUGT-UHFFFAOYSA-N 3-octadec-1-enylpyrrolidine-2,5-dione Chemical compound CCCCCCCCCCCCCCCCC=CC1CC(=O)NC1=O AZPVYDDUIKAUGT-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
- GFEGLPYYGVFJPB-UHFFFAOYSA-N CC1(CCCCC1)SP(O)(O)=S Chemical compound CC1(CCCCC1)SP(O)(O)=S GFEGLPYYGVFJPB-UHFFFAOYSA-N 0.000 description 1
- 101150009724 CYBA gene Proteins 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 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
- WIKSRXFQIZQFEH-UHFFFAOYSA-N [Cu].[Pb] Chemical compound [Cu].[Pb] WIKSRXFQIZQFEH-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
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- OTBHHUPVCYLGQO-UHFFFAOYSA-N bis(3-aminopropyl)amine Chemical compound NCCCNCCCN OTBHHUPVCYLGQO-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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 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-$l^{5}-phosphane Chemical compound CCCCOP(S)(=S)OCCCC XPRULOZMJZDZEF-UHFFFAOYSA-N 0.000 description 1
- IRDLUHRVLVEUHA-UHFFFAOYSA-N diethyl dithiophosphate Chemical compound CCOP(S)(=S)OCC IRDLUHRVLVEUHA-UHFFFAOYSA-N 0.000 description 1
- SWSCCSILRFOSMS-UHFFFAOYSA-N dihydroxy-(2-methylphenyl)sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CC1=CC=CC=C1SP(O)(O)=S SWSCCSILRFOSMS-UHFFFAOYSA-N 0.000 description 1
- KEZILVZPLVUKQG-UHFFFAOYSA-N dihydroxy-sulfanyl-sulfanylidene-$l^{5}-phosphane;pyrrolidine-2,5-dione Chemical compound OP(O)(S)=S.O=C1CCC(=O)N1 KEZILVZPLVUKQG-UHFFFAOYSA-N 0.000 description 1
- ZUNFAOLVHKUWCL-UHFFFAOYSA-N dipropoxy-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCCOP(S)(=S)OCCC ZUNFAOLVHKUWCL-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- UPCIBFUJJLCOQG-UHFFFAOYSA-L ethyl-[2-[2-[ethyl(dimethyl)azaniumyl]ethyl-methylamino]ethyl]-dimethylazanium;dibromide Chemical compound [Br-].[Br-].CC[N+](C)(C)CCN(C)CC[N+](C)(C)CC UPCIBFUJJLCOQG-UHFFFAOYSA-L 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
- 239000007788 liquid Chemical class 0.000 description 1
- 238000005461 lubrication Methods 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 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
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920006389 polyphenyl polymer 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
- 238000011160 research Methods 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
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- JZALLXAUNPOCEU-UHFFFAOYSA-N tetradecylbenzene Chemical compound CCCCCCCCCCCCCCC1=CC=CC=C1 JZALLXAUNPOCEU-UHFFFAOYSA-N 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
- C07D207/408—Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms
- C07D207/412—Acyclic radicals containing more than six carbon atoms
-
- 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
- C10M133/56—Amides; Imides
-
- 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
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Definitions
- This invention pertains to lubricating oil compositions havingincorporated therein metal-free detergents. These particular detergents are also effective 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.- Although these metalcontaining organic compounds have some effectiveness 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 I of forming ash depositsin 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 polyalkylene polyamine, followed by reaction with a dihydrocarbyl dithiophosphoric acid to form a salt thereof.
- alkenyl succinic anhydrides which are reactants herein are of the formula:
- polyalkylene polyamines which contribute the imide and the basic nitrogen atoms of the reaction products herein, are derived from polymers of ethylene or propylene, such as polyethylene polyamine, and polypropylene polyamines.
- polyethylene polyamine such as polyethylene polyamine, and polypropylene polyamines.
- Such polyalkylene polyamines may be represented by the formula wherein the R represents the divalent radical ethylene or propylene, and x is a number having a value from 1 to 10 or more.
- polyalkylene polyamines examples include diethylene triamine, triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine, dipropylene triamine, dipropylene tetramine, tetrapropylene pentarnine, pentapropylene hexamine, di-(trimethylene)- triamine, di(trimethylene)tetramine, tetra-(trimethylene)- pentamine and penta-(trimethylene)hexamine.
- dihydrocarbyl dithiophosphoric acids which are used in the salt formation herein are represented by the formula:
- R and R represent hydrocarbon radicals each having from 1 to 25 carbon atoms, preferably from 4m 20 carbon atoms.
- the R and R combined can have a total of from 6 to 50 carbon atoms, preferably from 10 to 40 carbon atoms.
- R and R radicals are exemplified as follows: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl, sec-amyl, hexyl, isohexyl, n-octyl, n-decyl, n-dodecyl, tetradecyl, octadecyl, cyclohexyl, phenyl, amylphenyl, hexadecylphenyl, etc.
- dihydrocarbyl dithiophosphoric acid examples include dimethyldithiophosphoric acid, methylethyldith-iophosphoric acid, diethyldithiophosphoric acid, di-n-propyldithiophosphoric acid, diisopropyldithiophosphoric acid, di-n-butyldithiophosphoric acid, diisobutyldithiophosphoric acid, n-butyl-n-amyldithiophosphoric acid, disecamyldithiophosphoric acid, methyl-n-hexyl-dithiophosphoric acid, isobutyl-n-hexyldithiophosphoric acid, di-noctyldithiophosphoric acid, methylcyclohexyl dithiophosphoric acid, methylcyclohexyldithiophosphoric acid,dicyclohexyldithiophosphoric acid, methylphenyldithiophosphoric acid,
- the reaction between a polyalkylene polyamine 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 polyalkylene polyamine to succinic anhydride can vary from 0.5:1 to 1:1.
- the polyamine-anhydride mol ratio is 0.8 to 1.
- succinimide the product obtained by the reaction of a polyalkylene polyamine and an alkenyl succinic anhydride will be termed a succinimide.
- the succinimides herein are reacted with a dihydrocarbyl dithiophosphoric acid at temperatures such that no hydrogen sulfide is evolved; that is, temperatures insufiicient for hydrogen sulfide formation.
- temperatures are from 50 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.
- salt means the product obtained by reacting the above-identified succinimide with the described dihydrocarbyl dithi-ophosphoric acid.
- salts include the dimethyl dithiophosphoric acid salt of N-(triethylene tetraminoethyl) octadecenyl succinimide, the isobutyl-n-hexyl dithiophosphoric acid salt of N-(d-iethylene triaminoethyl)hexacontenyl succinimide, the cyclohexyl phenyl dithiophosphoric acid salt of N-(ethylene diaminoethyl)hexatonenyl (C succinimide, and the diphenyl dithiophosphoric acid salt of N-(tripropylene tetraminoethyl)pentacontenyl succinimide.
- Lubricating oils which can be used as base oils include a wide variety of lubricating oils, such as naphthenic base, paraffin 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, sirberic 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
- the reaction of an alkenyl succinirnide with a polyalkylene polyamine is illustrated in the following example.
- EXAMPLE I Reaction product of tetraethylene pemamine and. polybutenyl succinic anhydride
- Table I hereinbelow presents further data on the effectiveness of the reaction products described herein as lubricating oil additives.
- the data of Table I were obtained under the severe conditions of a Caterpillar engine test under the Mil L45199 procedure. This Military specification procedure is so severe that the engine will not even operate with a base oil uncompounded. Even a base oil with the normal commercial additives under this procedure does not provide suificient lubrication; that is, the engine itself eventually sticks.
- the lubricating oil composition used in obtaining data for Table I consisted of the base oil having incorporated therein a product obtained by first reacting a polyisobutenyl succinic anhydride, wherein the polyisobutenyl pentamine in a 1:1 mol ratio as in Example I hereinabove, and the resulting imide was reacted with a di(alkylphenyl) dithiophosphoric acid wherein the alkyl radical was a polypropylene containing an average of about 13 carbon atoms.
- the succinirnide/dithiophosphoric acid mol ratio was 1:1.
- the amount of additive was equivalent to 10% by weight of the irnide.
- the PD Nos. refer to the piston discoloration rating. After the engine test, the three piston lands are examined visually. To a piston skirt which is completely black is assigned a PD No. of 800; to one which is completely clean, a PD No. of 0; to those intermediate between those completely black and completely clean are assigned PD Nos. intermediate in proportion to the extent and degree of darkening.
- the GD Nos. refer to the percentage deposit in the piston ring grooves; that is, a 0 evaluation being a clean groove, and a evaluation being a groove full of deposits.
- the base oil was a California paraffin-ic base oil having a viscosity of 500 SSU at 100 F.
- the base oil was a California paraflinic base oil having a viscosity of about 500 SSU at 100 F.
- Additive A was an alkenyl succinimide of tetraethylene pentamine wherein the alkenyl radical contained 66 carbon atoms.
- Additive B was the salt obtained by reacting 1 mol of the alkenyl succinimide of tetraethylene pentamine with 1 mol of an alkylphenyl dithiophosphoric acid, wherein the alkyl radical was derived from a propylene polymer having an average of from 12 to 14 carbon atoms.
- Adidtive C was the above-described alkylphenyl (lithiophosphoric acid.
- Copper Lead Table IV presents data obtained in a Caterpillar L-1 test, 120 hours.
- the base oil was a California solvent-refined SAE 30 base oil containing in amount of 1. 35% by weight, a product which was obtained by reacting a polyisobutenyl succinic anhydride with tetraethylene pentam-ine as in Example I hereinabove, and the resulting succinimide reacted with the above-described di(alylphenyl)dithiophosphoric acid.
- the succinirnide-dithiophosphoric acid mol ratio was about 1:1.
- the efiectiveness of the additives described herein in reducing bearing corrosion was further determined by evaluating a lubricating oil composition in an L38 test, using a 1 cylinder CLR engine in a test period of 40 hours.
- the lubricating oil composition consisted of a Mid- Continent SAE 30 base oil containing 2.26% by Weight of a product obtained by 1) reacting an alkenyl succinic anhydride and tetraethylene pentamine as in Example I, followed by (2) reacting the product of (1) with a dialkyl dithiophosphoric acid in a 1:1 mol ratio, wherein one alkyl radical contained 4 carbon atoms, and the second alkyl radical contained 5 carbon atoms.
- the bearing weight loss was only 67 mgs., as opposed to a weight loss of 5099 mgs. when using 3% by weight of the succinimide itself.
- 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 polyalkylene polyamine of the formula NH R(NHR) NH wherein R is a divalent radical selected from the group consisting of ethylene and propylene and x is a number having a value from 1 to 10, wherein the polyamine-anhydried mol ratio is from 0.5:1 to 1:1, followed by (2) reacting the product of (1) with dihydrocarbyl dithiophosphoric acid of the formula wherein R and R 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
- a lubricating oil composition comprising the composition of claim "1 in which the polyalkylene polyamine is tetraethylene pentamine and the dihydrocarbyl dithiophosphoric acid is alkylphenyl dithiophosphoric acid.
- a lubricating oil composition comprising the composition of claim 1 in which the polyalkylene polyamine is tetraethylene pentamine and the dihydrocarbyl dithiophosphoric acid is dialkyl dithiophosphoric acid.
- a lubricating oil composition comprisin the composition of claim 1 in which the polyalkylene polyamine is diethy-lene triamine and the dihydrocarbyl dithiophosphoric acid is alkyphenyl dithiophosphoric acid.
- a lubricating oil composition comprising a major proportion of an oil of lubricating viscosity and from 1% to 10% by weight of a product obtained by (1) reacting at 220 F. to 500 F. an alkenyl succinic anhydride having from 50 to 200 carbon atoms in the alkenyl radical with tetraethylene pentamine wherein the tetraethylene pentamine-anhydride mol ratio is from 0.5 :1 to 1:1 followed by (2) reacting the product of 1) at 150 F. to about 200 F. with a dihydrocarbyl dithiophosphoric acid of the formula References Cited by the Examiner UNITED STATES PATENTS 2,809,934 10/57 Alford et a1.
- R-O-P-SH column 4 line 46, for "Adidtive” read Additive column 5, line 8, for "di(aly1phenyl)” read di[alkylphenyl) lines 43 and 44, for "-anhydried” read ---anhydride column 6, line 5, for "550 F.” read 500 F. line 19, for "alkyphenyl” read alkylphenyl Signed and sealed this 7th day of December 1965.
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Description
United States Patent 3,185,643 OXIDATION RESISTANT LUBRICANTS Warren Lowe, Berkeley, and Frank A. Stuart, Oriuda, Califi, assignors to California Research Corporation, San Francisco, Calif., a corporation of Delaware N0 Drawing. Filed Sept. 28, 1962, Ser. No. 227,036 Claims. (Cl. 25232.7)
This invention pertains to lubricating oil compositions havingincorporated therein metal-free detergents. These particular detergents are also effective as oxidation inhibitors.
Present day internal combustion engines operate at high speeds and high compression ratios. When used in the socalled 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 efiicientoperating 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 metalcontaining organic compounds have some effectiveness 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 I of forming ash depositsin 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 compositions having incorporated'therein metal-free detergents which are also eifective 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 polyalkylene polyamine, 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 prod ucts remain remarkably free of deposits and varnish even under severe operating conditions.
The alkenyl succinic anhydrides which are reactants herein are of the formula:
3,185,643 Patented May 25, 1965 ice and polymers of mixtures of l-butene and isobutene hav= ing from 50 to 200 carbon atoms.
The polyalkylene polyamines, which contribute the imide and the basic nitrogen atoms of the reaction products herein, are derived from polymers of ethylene or propylene, such as polyethylene polyamine, and polypropylene polyamines. Such polyalkylene polyamines may be represented by the formula wherein the R represents the divalent radical ethylene or propylene, and x is a number having a value from 1 to 10 or more. Examples of these polyalkylene polyamines include diethylene triamine, triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine, dipropylene triamine, dipropylene tetramine, tetrapropylene pentarnine, pentapropylene hexamine, di-(trimethylene)- triamine, di(trimethylene)tetramine, tetra-(trimethylene)- pentamine and penta-(trimethylene)hexamine.
The dihydrocarbyl 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 25 carbon atoms, preferably from 4m 20 carbon atoms. The R and R combined can have a total of from 6 to 50 carbon atoms, preferably from 10 to 40 carbon atoms.
The R and R radicals are exemplified as follows: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl, sec-amyl, hexyl, isohexyl, n-octyl, n-decyl, n-dodecyl, tetradecyl, octadecyl, cyclohexyl, phenyl, amylphenyl, hexadecylphenyl, etc.
Examples of dihydrocarbyl dithiophosphoric acid include dimethyldithiophosphoric acid, methylethyldith-iophosphoric acid, diethyldithiophosphoric acid, di-n-propyldithiophosphoric acid, diisopropyldithiophosphoric acid, di-n-butyldithiophosphoric acid, diisobutyldithiophosphoric acid, n-butyl-n-amyldithiophosphoric acid, disecamyldithiophosphoric acid, methyl-n-hexyl-dithiophosphoric acid, isobutyl-n-hexyldithiophosphoric acid, di-noctyldithiophosphoric acid, methylcyclohexyl dithiophosphoric acid, methylcyclohexyldithiophosphoric acid,dicyclohexyldithiophosphoric acid, methylphenyldithiophosphoric acid, diphenyldithiophosphor-ic acid, di-(amylphenyDdithiophosphoric acid, di-(hexadecylphenyDdithiophosphoric acid, etc.
The reaction between a polyalkylene polyamine 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 polyalkylene polyamine to succinic anhydride can vary from 0.5:1 to 1:1. Preferably, the polyamine-anhydride mol ratio is 0.8 to 1.
For purposes of simplicity, the product obtained by the reaction of a polyalkylene polyamine and an alkenyl succinic anhydride will be termed a succinimide.
The succinimides herein are reacted with a dihydrocarbyl dithiophosphoric acid at temperatures such that no hydrogen sulfide is evolved; that is, temperatures insufiicient for hydrogen sulfide formation. Such temperatures are from 50 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.
As identified herein, the term salt means the product obtained by reacting the above-identified succinimide with the described dihydrocarbyl dithi-ophosphoric acid.
Examples of such salts include the dimethyl dithiophosphoric acid salt of N-(triethylene tetraminoethyl) octadecenyl succinimide, the isobutyl-n-hexyl dithiophosphoric acid salt of N-(d-iethylene triaminoethyl)hexacontenyl succinimide, the cyclohexyl phenyl dithiophosphoric acid salt of N-(ethylene diaminoethyl)hexatonenyl (C succinimide, and the diphenyl dithiophosphoric acid salt of N-(tripropylene tetraminoethyl)pentacontenyl succinimide.
Lubricating oils which can be used as base oils include a wide variety of lubricating oils, such as naphthenic base, paraffin 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, sirberic 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., monoalkylbenzene such as dodecyl benzene, tetradecyl benzene, etc.), and dialkyl benzenes (e.g., n-nonyl Z-ethyl hexyl benzene); polyphenyls (e.g., biphenyls and terphenyls), alkyl biphenyl ethers, polymers of silicon (e.g., tetraethyl silicate, tetraisopropyl silicates, tetra(4-rnethyl-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 The reaction of an alkenyl succinirnide with a polyalkylene polyamine is illustrated in the following example.
EXAMPLE I Reaction product of tetraethylene pemamine and. polybutenyl succinic anhydride A mixture of '84 grams (0.45 mol) of tetraethylene pentamine and 702 grams (0.45 mol) of a polybutenyl succinic anhydride wherein the polybutenyl radical was derived from a polyisobutene having a molecular Weight of about 1,000, was blended with agitation at 125 F. in a nitrogen atmosphere. The temperature was increased to 400 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. The reaction mixture was then allowed to reach room temperature at this reduced pressure. The reaction product contained 5.1% nitrogen.
Table I hereinbelow presents further data on the effectiveness of the reaction products described herein as lubricating oil additives. The data of Table I were obtained under the severe conditions of a Caterpillar engine test under the Mil L45199 procedure. This Military specification procedure is so severe that the engine will not even operate with a base oil uncompounded. Even a base oil with the normal commercial additives under this procedure does not provide suificient lubrication; that is, the engine itself eventually sticks.
The lubricating oil composition used in obtaining data for Table I consisted of the base oil having incorporated therein a product obtained by first reacting a polyisobutenyl succinic anhydride, wherein the polyisobutenyl pentamine in a 1:1 mol ratio as in Example I hereinabove, and the resulting imide was reacted with a di(alkylphenyl) dithiophosphoric acid wherein the alkyl radical was a polypropylene containing an average of about 13 carbon atoms. The succinirnide/dithiophosphoric acid mol ratio was 1:1. The amount of additive was equivalent to 10% by weight of the irnide.
The PD Nos. refer to the piston discoloration rating. After the engine test, the three piston lands are examined visually. To a piston skirt which is completely black is assigned a PD No. of 800; to one which is completely clean, a PD No. of 0; to those intermediate between those completely black and completely clean are assigned PD Nos. intermediate in proportion to the extent and degree of darkening.
The GD Nos. refer to the percentage deposit in the piston ring grooves; that is, a 0 evaluation being a clean groove, and a evaluation being a groove full of deposits.
The base oil was a California paraffin-ic base oil having a viscosity of 500 SSU at 100 F.
TABLE I Test results hours):
GD No. 51 PD Nos.--
Land 550, 200, 15, 0 Skirt 0 Table II hereinbelow presents data obtained from the L4 strip test, which is designed to evaluate the bearing corrosion characteristics of lubricating oil compositions. This test was run by immersing a copper-lead strip in the oil being tested for 20 hours at 340 F. The numbers in Table 11 represent the weight loss in milligrams.
The base oil was a California paraflinic base oil having a viscosity of about 500 SSU at 100 F.
Additive A was an alkenyl succinimide of tetraethylene pentamine wherein the alkenyl radical contained 66 carbon atoms.
Additive B was the salt obtained by reacting 1 mol of the alkenyl succinimide of tetraethylene pentamine with 1 mol of an alkylphenyl dithiophosphoric acid, wherein the alkyl radical was derived from a propylene polymer having an average of from 12 to 14 carbon atoms.
Adidtive C was the above-described alkylphenyl (lithiophosphoric acid.
TABLE II Mel Ratios, Composition Dithiophos- L-4 Test phoric Acid/ Result Succinimide 1. Base oil 2.8% wt. Additive A 1% wt.
Additive O 0. 36:1 52. 3 2. Base Oil 1.35% wt. Additive A 1% 7 wt. Additive C 0.75:1 67. 9 3. Base oil 3% wt. Additive B 1:1 4. 2
TABLE III Copper Lead Table IV presents data obtained in a Caterpillar L-1 test, 120 hours.
The base oil was a California solvent-refined SAE 30 base oil containing in amount of 1. 35% by weight, a product which was obtained by reacting a polyisobutenyl succinic anhydride with tetraethylene pentam-ine as in Example I hereinabove, and the resulting succinimide reacted with the above-described di(alylphenyl)dithiophosphoric acid. The succinirnide-dithiophosphoric acid mol ratio was about 1:1.
The efiectiveness of the additives described herein in reducing bearing corrosion was further determined by evaluating a lubricating oil composition in an L38 test, using a 1 cylinder CLR engine in a test period of 40 hours. The lubricating oil composition consisted of a Mid- Continent SAE 30 base oil containing 2.26% by Weight of a product obtained by 1) reacting an alkenyl succinic anhydride and tetraethylene pentamine as in Example I, followed by (2) reacting the product of (1) with a dialkyl dithiophosphoric acid in a 1:1 mol ratio, wherein one alkyl radical contained 4 carbon atoms, and the second alkyl radical contained 5 carbon atoms.
The bearing weight loss was only 67 mgs., as opposed to a weight loss of 5099 mgs. when using 3% by weight of the succinimide itself.
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 50 to 200 carbon atoms in the alkenyl radical with a polyalkylene polyamine of the formula NH R(NHR) NH wherein R is a divalent radical selected from the group consisting of ethylene and propylene and x is a number having a value from 1 to 10, wherein the polyamine-anhydried mol ratio is from 0.5:1 to 1:1, followed by (2) reacting the product of (1) with dihydrocarbyl dithiophosphoric acid of the formula wherein R and R 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 550 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 comprising the composition of claim "1 in which the polyalkylene polyamine is tetraethylene pentamine and the dihydrocarbyl dithiophosphoric acid is alkylphenyl dithiophosphoric acid.
3. A lubricating oil composition comprising the composition of claim 1 in which the polyalkylene polyamine is tetraethylene pentamine and the dihydrocarbyl dithiophosphoric acid is dialkyl dithiophosphoric acid.
4. A lubricating oil composition comprisin the composition of claim 1 in which the polyalkylene polyamine is diethy-lene triamine and the dihydrocarbyl dithiophosphoric acid is alkyphenyl dithiophosphoric acid.
5. A lubricating oil composition comprising a major proportion of an oil of lubricating viscosity and from 1% to 10% by weight of a product obtained by (1) reacting at 220 F. to 500 F. an alkenyl succinic anhydride having from 50 to 200 carbon atoms in the alkenyl radical with tetraethylene pentamine wherein the tetraethylene pentamine-anhydride mol ratio is from 0.5 :1 to 1:1 followed by (2) reacting the product of 1) at 150 F. to about 200 F. with a dihydrocarbyl dithiophosphoric acid of the formula References Cited by the Examiner UNITED STATES PATENTS 2,809,934 10/57 Alford et a1. 25232.7 2,973,323 2/61 Millikan et a1. 25232.7 2,995,568 8/61 Malz et a1. 260326.5 3,018,247 1/62 Anderson et a1. 252-327 3,058,910 10 /62 Clumer 252 32.7 3,074,990 1/63 Cyba 25232.7
DANIEL E. WYMAN, Primary Examiner.
UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3,185,643 May 25, 1965 Warren Lowe et a1.
It is hereby certified that error appears in the above numbered patent requiring correction and that the said Letters Patent should read as corrected below.
Column 2, lines 24 to 29, the formula should appear as shown below instead of as in the patent:
R-O-P-SH column 4, line 46, for "Adidtive" read Additive column 5, line 8, for "di(aly1phenyl)" read di[alkylphenyl) lines 43 and 44, for "-anhydried" read ---anhydride column 6, line 5, for "550 F." read 500 F. line 19, for "alkyphenyl" read alkylphenyl Signed and sealed this 7th day of December 1965.
(SEAL) Attest:
ERNEST W. SWIDER EDWARD J. BRENNER Attesting Officer Commissioner of Patents
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 POLYALKYLENE POLYAMINE OF THE FORMULA
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US3265618A (en) * | 1963-07-26 | 1966-08-09 | Shell Oil Co | Lubricating oil compositions |
US3284354A (en) * | 1963-12-12 | 1966-11-08 | Exxon Research Engineering Co | Reaction product of metal dithiophosphate, polyamine and alkenyl succinic acid or anhydride |
US3294684A (en) * | 1963-07-11 | 1966-12-27 | Standard Oil Co | Lubricant compositions containing detergency additives |
US3306908A (en) * | 1963-12-26 | 1967-02-28 | Lubrizol Corp | Reaction products of high molecular weight hydrocarbon succinic compounds, amines and heavy metal compounds |
US3324032A (en) * | 1964-12-22 | 1967-06-06 | Exxon Research Engineering Co | Reaction product of dithiophosphoric acid and dibasic acid anhydride |
US3397145A (en) * | 1958-12-29 | 1968-08-13 | Universal Oil Prod Co | Hydrocarbon oils containing alkylthiophosphoric acid salts of polymeric condensation products |
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 |
US3844960A (en) * | 1970-11-06 | 1974-10-29 | Shell Oil Co | Lubricant compositions |
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US3397145A (en) * | 1958-12-29 | 1968-08-13 | Universal Oil Prod Co | Hydrocarbon oils containing alkylthiophosphoric acid salts of polymeric condensation products |
US3502677A (en) * | 1963-06-17 | 1970-03-24 | Lubrizol Corp | Nitrogen-containing and phosphorus-containing succinic derivatives |
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US3623985A (en) * | 1967-03-29 | 1971-11-30 | Chevron Res | Polysuccinimide ashless detergents as lubricating oil additives |
US3844960A (en) * | 1970-11-06 | 1974-10-29 | Shell Oil Co | Lubricant compositions |
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