US2976238A - Oil-based compositions - Google Patents
Oil-based compositions Download PDFInfo
- Publication number
- US2976238A US2976238A US703753A US70375357A US2976238A US 2976238 A US2976238 A US 2976238A US 703753 A US703753 A US 703753A US 70375357 A US70375357 A US 70375357A US 2976238 A US2976238 A US 2976238A
- Authority
- US
- United States
- Prior art keywords
- oil
- complex
- zinc
- compound
- compositions
- 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
- 239000000203 mixture Substances 0.000 title claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 54
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 17
- 229910052725 zinc Inorganic materials 0.000 claims description 17
- 239000011701 zinc Substances 0.000 claims description 17
- -1 COLBALT Chemical compound 0.000 claims description 13
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 5
- 239000010687 lubricating oil Substances 0.000 claims description 5
- 229910052718 tin Inorganic materials 0.000 claims description 5
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052804 chromium Inorganic materials 0.000 claims description 4
- 239000011651 chromium Substances 0.000 claims description 4
- 229910052793 cadmium Inorganic materials 0.000 claims description 3
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003921 oil Substances 0.000 description 42
- 238000012360 testing method Methods 0.000 description 32
- 229910052751 metal Inorganic materials 0.000 description 27
- 239000002184 metal Substances 0.000 description 27
- 239000002480 mineral oil Substances 0.000 description 24
- 235000010446 mineral oil Nutrition 0.000 description 24
- 150000001412 amines Chemical class 0.000 description 21
- 239000000654 additive Substances 0.000 description 19
- 150000003839 salts Chemical class 0.000 description 19
- 239000000446 fuel Substances 0.000 description 15
- 239000000314 lubricant Substances 0.000 description 15
- 239000003208 petroleum Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 12
- 238000005260 corrosion Methods 0.000 description 11
- 230000007797 corrosion Effects 0.000 description 11
- 125000005609 naphthenate group Chemical group 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 8
- 230000001050 lubricating effect Effects 0.000 description 7
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000002199 base oil Substances 0.000 description 6
- 238000002485 combustion reaction Methods 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 229940126062 Compound A Drugs 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000005864 Sulphur Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 230000003749 cleanliness Effects 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 235000019388 lanolin Nutrition 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 4
- 239000011135 tin Substances 0.000 description 4
- 229960001124 trientine Drugs 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000010688 mineral lubricating oil Substances 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229960000314 zinc acetate Drugs 0.000 description 3
- 239000004246 zinc acetate Substances 0.000 description 3
- 240000005020 Acaciella glauca Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 241000158728 Meliaceae Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229940057499 anhydrous zinc acetate Drugs 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical class CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 239000011133 lead Substances 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000010705 motor oil Substances 0.000 description 2
- 229940049964 oleate Drugs 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 150000003016 phosphoric acids Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 235000003499 redwood Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000010736 steam turbine oil Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- 239000010723 turbine oil Substances 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- 150000003751 zinc Chemical class 0.000 description 2
- DJWUNCQRNNEAKC-UHFFFAOYSA-L zinc acetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O DJWUNCQRNNEAKC-UHFFFAOYSA-L 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- 229910000906 Bronze Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 101100257011 Mus musculus Skil gene Proteins 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000021053 average weight gain Nutrition 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 239000010974 bronze Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000010727 cylinder oil Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- MFGZXPGKKJMZIY-UHFFFAOYSA-N ethyl 5-amino-1-(4-sulfamoylphenyl)pyrazole-4-carboxylate Chemical compound NC1=C(C(=O)OCC)C=NN1C1=CC=C(S(N)(=O)=O)C=C1 MFGZXPGKKJMZIY-UHFFFAOYSA-N 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
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 1
- 229940012189 methyl orange Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000012261 resinous substance Substances 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical class [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- JDLYKQWJXAQNNS-UHFFFAOYSA-L zinc;dibenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JDLYKQWJXAQNNS-UHFFFAOYSA-L 0.000 description 1
- ZBDJNBFTEIUHPK-UHFFFAOYSA-L zinc;dihexoxy-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].CCCCCCOP([S-])(=S)OCCCCCC.CCCCCCOP([S-])(=S)OCCCCCC ZBDJNBFTEIUHPK-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/18—Complexes with metals
-
- 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
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/108—Residual fractions, e.g. bright stocks
-
- 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
- C10M2205/18—Natural waxes, e.g. ceresin, ozocerite, bees wax, carnauba; Degras
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/16—Groups 8, 9, or 10
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/135—Steam engines or turbines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/252—Diesel engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/252—Diesel engines
- C10N2040/253—Small diesel engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
- C10N2040/26—Two-strokes or two-cycle engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
Definitions
- This invention is for improvements in or relating to oil-based compositions and is particularly concerned with lubricating compositions.
- a further object of the present invention is to provide oil-based compositions having anti-corrosive properties.
- a cylinder lubricant for marine diesel engines operating on boiler fuel or other fuel of high sulphur content which lubricant comprises a mineral lubricating oil having incorporated therein an oilsoluble organic nonaromatic amine having not less than 7 carbon atoms or an oil-soluble non-aromatic amine salt of a weak acid, said organic non-aromatic amine or amine salt being present in an amount sufficient to provide at least of amine in the oil.
- the non-aromatic amines of this application effectively reduce cylinder Wear and improve piston cleanliness of marine diesels operating on boiler fuel, but they suffer from certain disadvantages in that they possess strong odours and have a caustic action on the skin, are prone to cause the removal of paint from surfaces with which they come into contact, and tend to react with carbon dioxide in the atmosphere with the consequent formation of oil-insoluble carbonates or carbamates which form an undesirable skin on the surface.
- the amine salts on the other hand, those which have adequate oil-solubility, while free from these objections, have rather low neutralisation equivalents which necessitate their use in inconveniently large amounts.
- compositions of the present invention incorporate oil-soluble compounds of mild odour which compounds are substantially neutral in reaction, yet they have higher neutralisation equivalents and can therefore be used in smaller amounts.
- compositions of the present invention may be employed as lubricants for small two-stroke engines. While conventional mineral lubricating oils may be used for this purpose, the presence of additives to improve piston cleanliness and disperse or soften carbon deposits is often desirable.
- oil-based compositions of the present invention may also be used as storage oils, slushing compositions and general rust-preventing compositions such compositions including, if desired, conventional additives such as metal petroleum (mahogany) sulphonates, wool grease and the like.
- compositions of the present invention may also be employed as lubricants for steam turbines, such lubricants possessing good rust-preventive properties in the presence of water or salt water; conventional antioxidants will also generally be present in such compositions.
- an oil-based composition comprising a mineral or synthetic oil having incorporated therein a proportion of a compound having the general formula wherein M is a polyvalent metal capable of forming ammino co-ordination complexes, A is the residue of an organic acid, B is an organic dior poly-amine, x and y are small integers satisfying the valency of M and A, z is a small integer such that the co-ordination number of M is partially or completely satisfied, and A and B are selected so that the compound is soluble in the oil.
- M is a polyvalent metal capable of forming ammino co-ordination complexes
- A is the residue of an organic acid
- B is an organic dior poly-amine
- x and y are small integers satisfying the valency of M and A
- z is a small integer such that the co-ordination number of M is partially or completely satisfied
- a and B are selected so that the compound is soluble in the oil.
- the radical A has preferably one of the following where R and R are alkly, cycloalkyl, aralkyl, alkaryl or aryl groupings, and may carry substituents such as hydroxyl or ester groups or halogen atoms.
- the metal M must be a metal capable of forming relatively stable ammino co-ordination complexes, and is desirably also a metal which is not prone to increase the oxidation rate of the oil in which it is dissolved.
- the preferred metals are zinc, cadmium, cobalt, tin, lead, nickel and chromium, although others, such as copper, iron (ferrous), mercury, silver, manganese and the rare or comparatively rare elements of group VIII of the periodic table, e.g. platinum, palladium, ruthenium, osmium or iridium, may be used if desired.
- the complex amino compounds employed as the additives in the present invention may be prepared by reacting a salt M A with the organic dior poly-amine.
- Suitable salts M A are the acetates,
- ctoates laurates, oleates, naphthenates, benzoates, alicylates, petroleum sulphonates, alklated aryl sulhonates and long chain alkyl and alkylated aryl hosphates.
- di or poly-amines B examples are ethylene dimine, diethylene triamine, triethylene tetramine, tetrathylene pentamine, mixtures of higher polyethylene olyamines, piperazine, p-phenylene diamine and various ommercially available long-chain diamines of the genral formula R"--NHCH CH CH NH wherein R rep- :sents an alkyl group derived from a fatty acid, e.g. iuric acid or from mixed fatty acids obtained from oconut oil, soya bean oil or tallow, these diamines being Jld under the registered trademark Duomeen.
- a fatty acid e.g. iuric acid or from mixed fatty acids obtained from oconut oil, soya bean oil or tallow
- heterocyclic dior poly-amines may be emloyed, examples of suitable compounds being. sold uner the trademark Bitran.
- the complex ammino compounds When the complex ammino compounds are intended I be employed as additives for lubricating oils which re to be subjected to relatively high temperatures, it is ecessary to select compounds derived from long-chain ior poly-amines, since compounds derived, for exmple, from the polyethylene polyamines tend to decomose with the formation of resinous substances which :nd to form objectionable gums on pistons, etc. Thus hen, for example, the complex compounds are to be nployed in lubricating compositions for 1.0. engine oils is desirable to select those derived from the )uomeens or other long-chain dior poly-amines.
- the complex ammino compounds may be prepared by my means known to the art.
- those made from il-soluble metal soaps or salts may conveniently be repared in solution, e.g. in mineral oil, by simply warmg with the dior poly-amine in the appropriate proporans, Generally the molar ratio of amine to metal salt ill not exceed 1:1, and it is often advantageous tohave l Ilid oil-insoluble metal salts, a convenient method is i reflux a solution of the dior poly-amine in petroleum her or benzene with a slight excess of the salt until the tter passes into solution, after which the solution is tered and the solvent removed by distillation.
- Comex compounds of this type are in general readily solue in hot mineral oil but tend to separate to some exnt on cooling.
- More useful mixed complexes can be 'epared by further reacting the oil-insoluble metal lt/amine complex with a proportion of an oil-soluble etal salt in such amounts that the molar ratio of total etal salts to the dior poly-amine is at least l:0.8.
- oil-soluble complex ammino umpounds of the present invention are:
- nc naphthenate/diethylene triamine complex (1:0.8 molar ratio) nc acetate/Duomeen C complex nc naphthenate/Duomeen C complex nc naphthenate/Bitran P complex nc oleate/Duomeen C complex :ad naphthenate/Duomeen C complex :ad naphthenate/triethylene tetramine complex nc naphthenate/p-phenylene diamine complex Nickel petroleum sulphonate/Duomccn C complex Cadmium octyl phosphate/Duomeen C complex
- the complex ammino compound is of the type described in British patent application No. 39,206/56. Specific examples of complex compounds of this type are:
- complex compounds may be prepared from certain commercially available materials having a relatively high organic acidity, e.g. crude wool grease. These may be neutralised directly with a suitable metal oxide or hydroxide, e.g. zinc oxide, and then complexed with the desired amine.
- a suitable metal oxide or hydroxide e.g. zinc oxide
- the most generally useful complex compounds are those prepared from freely oil-soluble metal salts e.g. the laurates, oleates and, particularly, the naphthenates of metals such as zinc, nickel, cobalt, tin and chromium and long-chain diamines, particularly the Duomeens.
- the Duomeens have the general formula R"-NHCH CH CH NH the radical R" being derived from a fatty acid, and substances are commercially available in which R" is derived from coconut fatty acids (Duomeen C), soya fatty acids (Duomeen S) and tallow fatty acids (Duomeen T).
- Duomeen C any of these substances may be employed in the production of the complex compounds, but it is generally preferred to use Duomeen C as this substance has the best oilsolubility and the highest neutralisation equivalent.
- Zinc is generally the preferred metal both for economic reasons and because the zinc salts of organic acids can readily be prepared by direct neutralisation of the acids with zinc oxide in the presence of a little water. To obtain the maximum oil-solubility, particularly at low temperatures, it is generally desirable to have a small excess jofthe metal salt present, a molar ratio of saltzamine'of 1:0.8 being particularly suitable.
- Complex compounds of this general type are suitable for use in a variety of lubricating compositions in accordance with the present invention.
- Complex compounds having adequate oil-solubility may also be prepared from freely oil-soluble metal salts, e.g. zinc naphthenate, and diethylene triamine or other polyethylene polyamines. These may be used equally well'as corrosion inhibitors in steam turbine oils, but as already indicated their use should not be considered in lubricants liable to be subjected to relatively high temperatures.
- the additives of the present invention may be employed, if desired, in conjunction with other additives commonly used in lubricating oils.
- oils for internal combustion engines there may be present conventional detergents such as metal petroleum (mahogany) sulphonates, and antioxidants such as zinc dialkyl dithiophosphates, metal alkyl phenol sulphides or phosphorised sulphurised terpenes.
- the additives may be employed not only in mineral lubricating oils but also in synthetic oils, e.g. the dicarboxylic acid diester type and the polyglycol ether type of synthetic lubricant.
- oil-based compositions of the present invention are employed as lubricants for the cylinders of marine diesel engines operating on boiler fuel or other fuel of high sulphur content they may contain from 2 percent to 20 percent by weight of the complex ammino compound.
- the additive is preferably used in a proportion of from 0.5 to 2 percent.
- additives For use in turbine oils, selected additives may be used in concentrations ranging from 0.02% to 2.0% and preferably from 0.05% to 0.2%. In general rust-preventive compositions the additives may be employed in widely differing amounts depending on the application which is in mind; thus from about 0.1% up to or even 20% may be used depending on the severity of the conditions.
- EXAMPLE 1 Zinc naphthenate diethylene triamine complex (Compound A) To 709 grams (0.55 mol) of an approximately 50% solution of zinc naphthenate in mineral oil were added 51.5 grams (0.5 mol) of diethylene triamine. An exothermic reaction took place, following which the material was stirred at 110 C. for minutes. The product was a brown oil containing 4.8% zinc and 2.7% nitrogen, and was freely soluble in mineral oil although diethylene triamine itself was quite insoluble.
- the reserve alkalinity of this complex compond was found to be 176 mgs. KOH per gram, the reserve alkalinity of the original zinc naphthenate concentrate being about 80 mgs. KOH per gram.
- Reserve alkalinity was determined by refluxing a weighed quantity of the sample with a known excess of 0.1 N HQ in a solution consisting of 5% methanol 45% ethanol 50% water and back-titrating with 0.1 N NaOH using screened methyl orange as indicator.
- the product was freely miscible with mineral oil although the oil-solubility of Duomeen C itself was very limited. It contained 4.3% zinc and had a reserve alkalinity" of about 110.
- the product contained 13.6% zinc and had a reserve alkalinity of about 550 mgs. KOH per gm. It was readily soluble in hot mineral oil but some separation occurred on cooling.
- EXAMPLE 4 Zinc acetate-naphthenate Duomeen C complex (1:0.5:1 molar ratio) A mixture of 18.35 gms. (0.1 mol) of anhydrous Zinc acetate and 25.0 gms. (0.1 mol) of Duomeen C were stirred together in a beaker and heated slowly to 130 C. Most of the zinc acetate appeared to react in the temperature range to C. yielding a butt opaque viscous liquid. 53.6 grams (0.05 mol) of an approximately 50% oil solution of zinc naphthenate was now added and heating and stirring continued for a few minutes. The zinc naphthenate employed contained 12% zinc. The product was mixed with filter-aid and filtered hot. On dilution with an equal weight of mineral oil a clear stable 36% oil concentrate was obtained containing 5.2% of zinc and having a reserve alkalinity of about mgs. KOH per gram.
- the product was a dark brown solid containing 3.04%
- Example 3 By the general procedure outlined above, a large number of complex compounds suitable for use in the oilbased compositions of the present invention, may be prepared.
- the direct heating method of Examples 1 and 2 is generally the preferred method, but various compounds derived from oil-insoluble metal salts, e.g. zinc benzoate, zinc salicylate, may be made by the method of Example 3.
- the amount to be complexed ith the metal salt was calculated from a determination Ethe basicity of the amine.
- Oil A was a mineral oil having a viscosity of about i seconds Redwood I at 140 F. and oil B was a lvent-refined oil of viscosity about 65 seconds Redwood it 140 F.
- compositions of the present vention were subjected to a very severe test applicable anticorrosive engine lubricating oils designed to pro- :t aero-engines from corrosion during storage and shipent overseas.
- Mineral oil C was a conventionally refined paraffinic brightstock of viscosity about 600 seconds Redwood I at F.
- No. 1 cylinder was lubricated mechanically, the rate of feed of the test oil to this cylinder being 20 cc. per hour per lubricator Le. 40 cc. per hour total.
- Mineral oil D was a solvent-refined mineral oil of viscosity approximately seconds Redwood l at 140 F.
- compositions of the present invention have only a mild odour, are without caustic action on the skin and do not remove paint. Furthermore, they are stable on storage over long periods and do not react with carbon dioxide in the atmosphere. They are also without significant action on metals such as copper, brass, Phosphor bronze, zinc and aluminium at the temperatures encountered in service.
- An oil-based composition consisting essentially of a lubricating oil having incorporated therein from 2% to 30% by weight of an oil-soluble complex ammino compound having the general formula M A B wherein M is selected from the group consisting of zinc, cadmium, cobalt, tin, lead, nickel and chromium; A is selected from the group consisting of engine tests. Results of the tests are summarized in R.0 o 0- R.SOz- RO-P-0- Table V. 0
- composition as claimed in claim 1 herein the ubricating oil is a mineral oil.
- composition as claimed in claim 1 wherein the lbricating oil is selected from the'groupconsisting of icarboxylic acid diester oils and pblyglycolether oils.
- composition as claimed in claim 1 wherein the omplex ammino compound is a complex consisting of inc naphthenate/R"-NHCH CH CH NH wherein R" a an alkyl group having from 8 to l8 carbon atoms.
- composition as claimed in claim 1 wherein the omplex ammino compound is a complex consisting of inc oleate/R"NHCH CI I CH NH wherein R" is an lkyl group having from 8 to 18 atoms.
- composition as claimed in claim 1 wherein the omplex ammino compound is a complex consisting of :ad naphthenate/ "NHCH CH CH NH wherein R" i an alkyl group having from 8 to 18 carbon atoms.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2976238X | 1956-12-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2976238A true US2976238A (en) | 1961-03-21 |
Family
ID=10918947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US703753A Expired - Lifetime US2976238A (en) | 1956-12-24 | 1957-12-19 | Oil-based compositions |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2976238A (en(2012)) |
| NL (1) | NL103587C (en(2012)) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3093585A (en) * | 1960-06-06 | 1963-06-11 | Shell Oil Co | Ester base lubricant compositions |
| US3192158A (en) * | 1962-04-18 | 1965-06-29 | Shell Oil Co | Lubricating compositions containing a detergent copolymer and an alkaline earth petroleum sulfonate-trialkyl amine complex |
| US3331774A (en) * | 1965-08-13 | 1967-07-18 | Pennsalt Chemicals Corp | Grease compositions |
| US3331775A (en) * | 1966-10-04 | 1967-07-18 | Pennsalt Chemicals Corp | Lubricating compositions |
| US3332873A (en) * | 1965-08-13 | 1967-07-25 | Pennsalt Chemicals Corp | Phosphate ester greases |
| US3791804A (en) * | 1969-10-10 | 1974-02-12 | Standard Oil Co | Fuel and lubricating oil additives transition metal complexes |
| WO1987004454A3 (en) * | 1986-01-21 | 1987-09-11 | Lubrizol Corp | Lubricant composition containing transition metals for viscosity control |
| WO1991018075A1 (en) * | 1990-05-16 | 1991-11-28 | N.V. Bekaert S.A. | Additive for lubricants containing a metal complex |
| US5650382A (en) * | 1993-01-14 | 1997-07-22 | N.V. Bekaert S.A. | Additive for lubricants containing a metal complex |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB696064A (en) * | 1950-02-27 | 1953-08-26 | Wakefield & Co Ltd C C | Lubricating compositions |
| US2684292A (en) * | 1951-03-13 | 1954-07-20 | Shell Dev | Fuel oil composition |
| US2692858A (en) * | 1950-05-12 | 1954-10-26 | Wakefield & Co Ltd C C | Castor oil lubricating composition |
| US2696473A (en) * | 1951-06-20 | 1954-12-07 | Texas Co | Halogen containing extreme pressure lubricant stabilized with a polyalkylene polyamine |
| US2736658A (en) * | 1952-07-23 | 1956-02-28 | Armour & Co | Method of protecting metal surfaces from corrosion and corrosion inhibitor compositions |
| US2737492A (en) * | 1952-03-26 | 1956-03-06 | American Cyanamid Co | Lubricating oil compositions |
| US2752311A (en) * | 1952-07-26 | 1956-06-26 | Texas Co | Lubricant containing a metal derivative of a hydroxyarylakyl polaymine and a metal dithiocarbamate |
| US2798045A (en) * | 1954-09-27 | 1957-07-02 | Shell Dev | Lubricating compositions |
| US2805996A (en) * | 1954-09-20 | 1957-09-10 | Pennsalt Chemicals Corp | Process for the production of oil soluble amine complexes and compositions containing such complexes |
| US2808376A (en) * | 1955-12-29 | 1957-10-01 | California Research Corp | Corrosion inhibited lubricant composition |
-
0
- NL NL103587D patent/NL103587C/xx active
-
1957
- 1957-12-19 US US703753A patent/US2976238A/en not_active Expired - Lifetime
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB696064A (en) * | 1950-02-27 | 1953-08-26 | Wakefield & Co Ltd C C | Lubricating compositions |
| US2692858A (en) * | 1950-05-12 | 1954-10-26 | Wakefield & Co Ltd C C | Castor oil lubricating composition |
| US2684292A (en) * | 1951-03-13 | 1954-07-20 | Shell Dev | Fuel oil composition |
| US2696473A (en) * | 1951-06-20 | 1954-12-07 | Texas Co | Halogen containing extreme pressure lubricant stabilized with a polyalkylene polyamine |
| US2737492A (en) * | 1952-03-26 | 1956-03-06 | American Cyanamid Co | Lubricating oil compositions |
| US2736658A (en) * | 1952-07-23 | 1956-02-28 | Armour & Co | Method of protecting metal surfaces from corrosion and corrosion inhibitor compositions |
| US2752311A (en) * | 1952-07-26 | 1956-06-26 | Texas Co | Lubricant containing a metal derivative of a hydroxyarylakyl polaymine and a metal dithiocarbamate |
| US2805996A (en) * | 1954-09-20 | 1957-09-10 | Pennsalt Chemicals Corp | Process for the production of oil soluble amine complexes and compositions containing such complexes |
| US2798045A (en) * | 1954-09-27 | 1957-07-02 | Shell Dev | Lubricating compositions |
| US2808376A (en) * | 1955-12-29 | 1957-10-01 | California Research Corp | Corrosion inhibited lubricant composition |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3093585A (en) * | 1960-06-06 | 1963-06-11 | Shell Oil Co | Ester base lubricant compositions |
| US3192158A (en) * | 1962-04-18 | 1965-06-29 | Shell Oil Co | Lubricating compositions containing a detergent copolymer and an alkaline earth petroleum sulfonate-trialkyl amine complex |
| US3331774A (en) * | 1965-08-13 | 1967-07-18 | Pennsalt Chemicals Corp | Grease compositions |
| US3332873A (en) * | 1965-08-13 | 1967-07-25 | Pennsalt Chemicals Corp | Phosphate ester greases |
| US3331775A (en) * | 1966-10-04 | 1967-07-18 | Pennsalt Chemicals Corp | Lubricating compositions |
| US3791804A (en) * | 1969-10-10 | 1974-02-12 | Standard Oil Co | Fuel and lubricating oil additives transition metal complexes |
| WO1987004454A3 (en) * | 1986-01-21 | 1987-09-11 | Lubrizol Corp | Lubricant composition containing transition metals for viscosity control |
| WO1991018075A1 (en) * | 1990-05-16 | 1991-11-28 | N.V. Bekaert S.A. | Additive for lubricants containing a metal complex |
| BE1004265A3 (nl) * | 1990-05-16 | 1992-10-20 | Bekaert Sa Nv | Additief voor smeermiddelen omvattende een metaalcomplex. |
| TR25289A (tr) * | 1990-05-16 | 1993-01-01 | Bekaert Sa Nv | Yaglayicilar icin bir metal kompleksi iceren katki maddesi |
| AU653522B2 (en) * | 1990-05-16 | 1994-10-06 | N.V. Bekaert S.A. | Additive for lubricants containing a metal complex |
| US6150308A (en) * | 1990-05-16 | 2000-11-21 | Deruyck; Frank | Additive for lubricants containing a metal complex |
| US5650382A (en) * | 1993-01-14 | 1997-07-22 | N.V. Bekaert S.A. | Additive for lubricants containing a metal complex |
Also Published As
| Publication number | Publication date |
|---|---|
| NL103587C (en(2012)) |
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