US3351647A - Nitrogen, phosphorus and metal containing composition - Google Patents
Nitrogen, phosphorus and metal containing composition Download PDFInfo
- Publication number
- US3351647A US3351647A US280452A US28045263A US3351647A US 3351647 A US3351647 A US 3351647A US 280452 A US280452 A US 280452A US 28045263 A US28045263 A US 28045263A US 3351647 A US3351647 A US 3351647A
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- US
- United States
- Prior art keywords
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- heated
- content
- oil
- 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
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- 239000000203 mixture Substances 0.000 title description 82
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title description 38
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title description 24
- 229910052698 phosphorus Inorganic materials 0.000 title description 24
- 239000011574 phosphorus Substances 0.000 title description 24
- 229910052751 metal Inorganic materials 0.000 title description 23
- 239000002184 metal Substances 0.000 title description 23
- 229910052757 nitrogen Inorganic materials 0.000 title description 21
- -1 hydrocarbon radical Chemical class 0.000 description 91
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 78
- 239000003921 oil Substances 0.000 description 33
- 235000019198 oils Nutrition 0.000 description 33
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- 125000004432 carbon atom Chemical group C* 0.000 description 18
- 239000000706 filtrate Substances 0.000 description 18
- 239000000314 lubricant Substances 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 16
- 150000001412 amines Chemical class 0.000 description 16
- 150000003839 salts Chemical class 0.000 description 16
- 239000011593 sulfur Substances 0.000 description 16
- 229910052717 sulfur Inorganic materials 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 15
- 238000001914 filtration Methods 0.000 description 15
- 239000007788 liquid Substances 0.000 description 15
- 239000010687 lubricating oil Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- 239000011787 zinc oxide Substances 0.000 description 15
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 14
- 150000003751 zinc Chemical class 0.000 description 14
- 229910052725 zinc Inorganic materials 0.000 description 14
- 239000011701 zinc Substances 0.000 description 14
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 13
- 239000002480 mineral oil Substances 0.000 description 13
- 235000010446 mineral oil Nutrition 0.000 description 13
- 230000003647 oxidation Effects 0.000 description 13
- 238000007254 oxidation reaction Methods 0.000 description 13
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- MXPWYMOGGGKKKM-UHFFFAOYSA-N phosphinodithioic acid Chemical compound SP=S MXPWYMOGGGKKKM-UHFFFAOYSA-N 0.000 description 11
- 239000000654 additive Substances 0.000 description 10
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 10
- 239000010802 sludge Substances 0.000 description 10
- 239000004215 Carbon black (E152) Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 229930195733 hydrocarbon Natural products 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 230000005540 biological transmission Effects 0.000 description 8
- OHJRPLUOKNMSMG-UHFFFAOYSA-N bis(2-propan-2-ylphenyl)-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CC(C)C1=CC=CC=C1P(S)(=S)C1=CC=CC=C1C(C)C OHJRPLUOKNMSMG-UHFFFAOYSA-N 0.000 description 8
- 239000002966 varnish Substances 0.000 description 8
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 239000010688 mineral lubricating oil Substances 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 230000001050 lubricating effect Effects 0.000 description 6
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- KZFPJCGEOBHFRG-UHFFFAOYSA-N bis(2-chlorophenyl)-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound C=1C=CC=C(Cl)C=1P(=S)(S)C1=CC=CC=C1Cl KZFPJCGEOBHFRG-UHFFFAOYSA-N 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical class ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 159000000009 barium salts Chemical class 0.000 description 4
- 229910052793 cadmium Inorganic materials 0.000 description 4
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 229910052804 chromium Inorganic materials 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 4
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 4
- 229940112669 cuprous oxide Drugs 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 229940073644 nickel Drugs 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- UPWOEMHINGJHOB-UHFFFAOYSA-N oxo(oxocobaltiooxy)cobalt Chemical compound O=[Co]O[Co]=O UPWOEMHINGJHOB-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 4
- 231100000241 scar Toxicity 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- 229940014800 succinic anhydride Drugs 0.000 description 4
- SOANRMMGFPUDDF-UHFFFAOYSA-N 2-dodecylaniline Chemical compound CCCCCCCCCCCCC1=CC=CC=C1N SOANRMMGFPUDDF-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-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
- 229920002367 Polyisobutene Polymers 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
- 239000000920 calcium hydroxide Substances 0.000 description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 3
- 229940095643 calcium hydroxide Drugs 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- VPNOHCYAOXWMAR-UHFFFAOYSA-N docosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCN VPNOHCYAOXWMAR-UHFFFAOYSA-N 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011133 lead Substances 0.000 description 3
- 229910000464 lead oxide 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
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910000008 nickel(II) carbonate Inorganic materials 0.000 description 3
- ZULUUIKRFGGGTL-UHFFFAOYSA-L nickel(ii) carbonate Chemical compound [Ni+2].[O-]C([O-])=O ZULUUIKRFGGGTL-UHFFFAOYSA-L 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- IGMNNGMXLPTFPE-UHFFFAOYSA-N sulfanyl(sulfido)phosphanium Chemical class S[PH2]=S IGMNNGMXLPTFPE-UHFFFAOYSA-N 0.000 description 3
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- 229910000906 Bronze Inorganic materials 0.000 description 2
- 208000032544 Cicatrix Diseases 0.000 description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000005376 alkyl siloxane group Chemical group 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- SNAYPLRUSICJMY-UHFFFAOYSA-N bis(2-methylphenyl)-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CC1=CC=CC=C1P(S)(=S)C1=CC=CC=C1C SNAYPLRUSICJMY-UHFFFAOYSA-N 0.000 description 2
- CNEZRVDCIKFWCN-UHFFFAOYSA-N bis(2-octylnaphthalen-1-yl)-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound C1=CC=C2C(P(S)(=S)C3=C4C=CC=CC4=CC=C3CCCCCCCC)=C(CCCCCCCC)C=CC2=C1 CNEZRVDCIKFWCN-UHFFFAOYSA-N 0.000 description 2
- 239000010974 bronze Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- CXKCTMHTOKXKQT-UHFFFAOYSA-N cadmium oxide Inorganic materials [Cd]=O CXKCTMHTOKXKQT-UHFFFAOYSA-N 0.000 description 2
- CFEAAQFZALKQPA-UHFFFAOYSA-N cadmium(2+);oxygen(2-) Chemical compound [O-2].[Cd+2] CFEAAQFZALKQPA-UHFFFAOYSA-N 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 238000006388 chemical passivation reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 230000000881 depressing effect Effects 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- CLUOCCWZZAGLPM-UHFFFAOYSA-N diphenyl-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(=S)(S)C1=CC=CC=C1 CLUOCCWZZAGLPM-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- BTXXAILRDVTVKP-UHFFFAOYSA-N hexacontan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCN BTXXAILRDVTVKP-UHFFFAOYSA-N 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- AZVIZZLNFYXIPS-UHFFFAOYSA-N pentahexacontan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCN AZVIZZLNFYXIPS-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000037387 scars Effects 0.000 description 2
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- WJECKFZULSWXPN-UHFFFAOYSA-N 1,2-didodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1CCCCCCCCCCCC WJECKFZULSWXPN-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- SKDGWNHUETZZCS-UHFFFAOYSA-N 2,3-ditert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(O)=C1C(C)(C)C SKDGWNHUETZZCS-UHFFFAOYSA-N 0.000 description 1
- UGIJCMNGQCUTPI-UHFFFAOYSA-N 2-aminoethyl prop-2-enoate Chemical compound NCCOC(=O)C=C UGIJCMNGQCUTPI-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 239000004129 EU approved improving agent Substances 0.000 description 1
- 241000158728 Meliaceae Species 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
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- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C10M137/12—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond
- C10M137/14—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond containing sulfur
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- 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 System
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
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- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/022—Ethene
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- C10M2205/024—Propene
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- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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- C10M2205/026—Butene
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- C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/16—Naphthenic acids
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- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
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- C10M2207/28—Esters
- C10M2207/286—Esters of polymerised unsaturated acids
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- C10N2010/04—Groups 2 or 12
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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
- C10N2010/08—Groups 4 or 14
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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
- C10N2010/12—Groups 6 or 16
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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
- C10N2010/14—Group 7
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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
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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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/08—Resistance to extreme temperature
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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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
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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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
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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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
- C10N2040/13—Aircraft turbines
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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
- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
Definitions
- Phosphorusand nitrogen-containing compositions are prepared by reacting a metal salt of a phosphinodithioic acid, especially a zinc salt of a diarylphosphinodithioic acid, with an amine, especially an aliphatic amine having from one to about 40 carbon atoms.
- the compositions are useful as additives for lubricating oils and automatic transmission fluids, in which they act as oxidation inhibitors and anti-wear agents. They afford synergistic oxidation inhibition properties when used with phenyl beta-naphthylamine.
- This invention relates to novel compositions which are suitable for use as additives in lubricating compositions and more particularly it relates to a new class of compositions which are effective to inhibit oxidation in lubricating compositions and prevent wear of the metal surfaces being lubricated.
- oils such as conventional lubricating oils
- oils are subjected to extended periods of use, especially at high operating temperatures, they tend to decompose and form complex and objectionable oxidation and decomposition products including peroxides and organic acids.
- These substances possess corrosive and other deleterious properties and, unless neutralized or counteracted, will attack and damage engine metallic parts.
- These acids furthermore, may go through a chemical process whereby the molecules combine or polymerize into large aggregates to form lacquer-like deposits on or between the moving parts of the engine, causing excessive wearing or even sticking of operating parts.
- Another object of this invention is to provide methods of preparing these new chemical compounds.
- Another object of this invention is to provide additives for lubricating compositions.
- Still another object of this invention is to provide new lubricating compositions.
- a phosphorusand nitrogen-containing composition having the general formula wherein R is a substantially hydrocarbon radical; M is a metal selected from the group consisting of zinc, calcium, copper, nickel, cobalt, chromium, lead, and cadmium; A, B, and C are radicals selected from the class consisting of hydrogen and substantially hydrocarbon radicals; x is the valence of M; y is from about 0.5 to about 6.
- the R radicals of the nitrogenand phosphorus-containing compositions of this invention may be the same or different radicals including alkyl, aryl, aralkyl, alkaryl, cycloalkyl, and heterocyclic radical, as well as such radicals containing substitutents such as halogen, nitro, and the like.
- the aryl and alkaryl radicals are preferred, especially alkaryl radicals containing from 7 to about 26 carbon atoms.
- A, B, and C of the nitrogenand phosphorous-containing compositions may be hydrogen or a substantially hydrocarbon radical.
- Substantially hydrocarbon radicals represented by A, B, and C include alkyl, alkylol, aryl, aralkyl, alkaryl, cycloalkyl, aminoalkyl, and polyaminopolyalkene. These hydrocarbon radicals may contain from 1 to about 40 carbon atoms. However, where oilsolubility is a criterion, preferably, A and B are hydrogen radicals and C is an aliphatic radical containing at least about 12 carbon atoms.
- the value of y may range from about 0.5 to about 6 and preferably is within the range of from about 1 to about the valence of the metal (M), i.e., x.
- M metal
- equivalent weights of reactants used in processes to provide the compositions of this invention are based upon a consideration of the number of functional groups in a reactant, i.e., if there are two functional groups, then the equivalent weight is one-half the molecular weight.
- an equivalent weight of an amine will be that weight of amine containing one atomic weight of nitrogen and an equivalent weight of a phosphinodithioic acid or metal salt thereof will be that weight of phosphinodithioic acid or metal salt thereof containing one atomic weight of phosphorus.
- compositions of this invention may be prepared by reacting the metal salt of a phosphinodithioic acid ,with an amine.
- the indicated reaction between the amine and the metal salt is often exothermic and may be carried out in many cases simply by mixing the reactants at room temperature. It is preferred to carry out the reaction at a temperature from about 10 C. to about 150 C.
- novel compositions of this invention may be prepared, alternatively, by first forming a complex of the inorganic metal component with ammonia or an amine, followed by a double decomposition reaction of this inorganic metal complex with the sodium or potassium salt of a phosphinodithioic acid.
- a complexforming metallic salt such as zinc sulfate
- ammonium hydroxide such as sodium ammonium hydroxide
- zinc ammonium sulfate such as sodium salt of diphenyl phosphinodithioic acid
- the latter method is quite satisfactory in some instances, the former method is preferred.
- the metal salt reactants employed as above for producing compositions of this invention are derivatives of phosphinodithioic acids conforming to the general formula wherein R is a substantially hydrocarbon radical.
- the R groups of the phosphinodithioic acid may be the same or different radicals including alkyl, aryl, aralkyl, alkaryl, cycloalkyl, and heterocyclic radicals, as well as such radicals containing substituents such as halogen, nitro, and the like.
- aryl and alkaryl radicals are preferred.
- the phosphinodithioic acids may be prepared by the reaction of Grignard reagents with phosphorus pentasulfide (see Organo Phosphorus Compounds, G. M. Kosolapofi, p. 135, John Wiley and Son, New York, 1950).
- the preferred and more economical method for preparing the phosphinodithioic acid is that described in US. 2,797,238 wherein aromatic compounds having ionization constants less than 1 10- in water at 25 C. and having at least one hydrogen atom attached to an aromatic ring structure are reacted with P 5 in the presence of AlCl in amounts such that the ratio of moles of AlCl to moles of P 8 is at least one.
- alkyl aryl phosphinodithioic acids The preparation of alkyl aryl phosphinodithioic acids is accomplished by the reaction of an alkyl thiophosphine sulfide with an aromatic compound in the presence of aluminum chloride (see description by Newallis et al. in vol. 27, Journal of Organic Chemistry, page 3829).
- aromatic radicals are organic radicals containing at least one resonant ring structure, such as phenyl, naphthyl, anthracyl, phenanthryl, naphthacyl, crysyl, pyryl, tribenzyl, biphenyl, and terphenyl radicals, and the substitution products of these such as their alkylation products, halogenation products, nitration products, etc.
- alkylation products examples include tolyl, xylyl, di-ethylphenyl, iso-propylphenyl, n-propylphenyl, tert-butylphenyl, di-tert-butylphenyl, iso-butylphenyl, r1- butylphenyl, tert-amylphenyl, cyclohexylphenyl, methylcyclohexylphenyl, caprylphenyl, diisobutylphenyl, dioctylphenyl, laurylphenyl, cetylphenyl, parafiin wax substituted phenyl, dodecylphenyl, di-dodecylphenyl, etc.
- halogenation products include chlorophenyl, 2,6 dichlorophenyl, trichlorophenyl, 4 bromophenyl, monoand poly-chloroxenyl, monoand poly-chloronaphthyl, monoand poly-chloroanthracyl, methyl chlorophenyl, ethyl chlorophenyl, ethyl chloroanthracyl, etc.
- nitro product include nitrophenyl, nitroxenyl, methyl-nitrophenyl, butyl-nitrophenyl, etc.
- the salts of the organic phosphinodithioic acids used in preparing the novel compositions of this invention can be prepared by the usual salt forming reactions. These include the reaction of an organic phosphinodithioic acid with a metal powder, a metal hydroxide or metal oxide and the double decomposition reaction of the sodium or potassium salt of an organic phosphinodithioic acid with a metal halide or other suitable metal salt.
- the metals which may be used in accordance with the principle of this invention include zinc, calcium, copper, nickel, cobalt, chromium, lead, and cadmium.
- These metals may be incorporated in salts by direct reaction of a phosphinodithioi-c acid with, for example, zinc oxide, zinc hydroxide, calcium hydroxide, cuprous oxide, cupric oxide, nickel carbonate, cobaltous carbonate, or lead oxide, or by the double decomposition reaction of a sodium or potassium salt of a phosphinodithioic acid with, for example, cobaltous chloride, cobaltous nitrate, chromic nitrate, or chromous acetate.
- a phosphinodithioi-c acid with, for example, zinc oxide, zinc hydroxide, calcium hydroxide, cuprous oxide, cupric oxide, nickel carbonate, cobaltous carbonate, or lead oxide
- a sodium or potassium salt of a phosphinodithioic acid with, for example, cobaltous chloride, cobaltous nitrate, chromic nitrate, or chromous acetate.
- the method described in US. 2,809,979 may be employed, wherein a mixture of aromatic compounds selected from the class consisting of aromatic hydrocarbons and halogenated aromatic hydrocarbons, phosphorus pentasulfide, an aluminum halide selected from the class consisting of aluminum chloride and aluminum bromide, and a Zinc halide selected from the class consisting of Zinc chloride and zinc bromide, is heated at a temperature within the range of about 130 C. to about 250 C.
- Ammonia and many amines may be used to form the nitrogen and phosphorus-containing compositions of this invention.
- the N-containing reactants useful in producing the compositions of this invention conform for the most part to the structural formula wherein A, B, and C are radicals selected from the class consisting of hydrogen, alkyl, alkylol, aryl, aralkyl, alkaryl, cycloalkyl, aminoalkyl, and polyaminopolyalkylene. It will be appreciated that two of A, B, and C may be a single polyalkylene radical containing up to 5 carbon atoms. Preferably, at least one of A, B, and C is a hydrogen radical.
- N-containing reactants include ammonia, ethylamine, propylamine, isopropylamine, butylamine, cyclohexylamine, n-hexylamine, dodecylamine, didodecylamine, tridodecylamine, N-methyl octylamine, N-dodecyltrimethylene diamine, ethanolamine, triethanolamine, guanidine, tripropylamine, aniline, o-toluidine, benzidine, phenylenediamine, N,N li-sec-butylphenylene diamine, beta-naphthylamine, alpha-naphthylamine, morpholine, piperazine, methane diamine, cycl
- Aliphatic amines having from one to about 40 carbon atoms are preferred for the purposes of this invention. The preference is based largely upon the availability as well as the general compatibility with hydrocarbon materials, such as lubricating oils, paints, and fuels of the compositions of this invention derived from such amines.
- hydrocarbon materials such as lubricating oils, paints, and fuels of the compositions of this invention derived from such amines.
- examples of such aliphatic amines include tetracontylamine, tricontylamine, N heptylhexylamine, methylethyl-i propylamine, tirethylamine, octanol amine, and tripropanol amine.
- tertiary alkyl primary amines containing from about 10 to about carbon atoms.
- primary aliphatic amines having more than about 12 carbon atoms are preferred, e.g., tert-dodecylamine, tert-octadecylamine, behenylamine, stearylamine, docosanylamine, hexacontanylamine, and pentahexacontanylamine.
- compositions of this invention include the complexes of one equivalent of tert-dodecyl amine with one equivalent of the zinc salt of di-xylylphosphinodithioic acid; one equivalent of tert-octadecylamine with one equivalent of the calcium salt of bis-(dichlorophenyl)phosphinodithioic acid; one equivalent of propylamine with one equivalent of the cadmium salt of di- (octylphenyl)phosphinodithioic acid; one equivalent of aniline with one equivalent of the cupric salt of di-(pentylphenyl)phosphinodithioic acid; two equivalents of ethylene diamine with the one equivalent of the cobaltic salt of di-(octylnaphthyl)phosphinodithioic acid; one equivalent of tert-dodecylamine with one equivalent of the zinc salt of chlorophenyl isopropyl
- the complexes or reaction products of this invention are, for the most part, quite readily soluble in hydrocarbon liquids such as toluene, xylene, heptane, and hexane. In fact, in many cases it is desirable to form the compounds of this invention in liquid hydrocarbon media.
- Example 1 A mixture of 1,485 grams (13.2 moles) of chlorobenzene and 666 grams (3 moles) of P 8 is heated to 100 C. in 0.5 hour whereupon 998 grams (7.5 moles) of aluminum chloride is added. The resulting mixture is refluxed at 145 C. for 0.5 hour and then heated for 4 hours at 160-165 C. The product mixture is cooled and mixed with 1,914 grams of toluene. The toluene mixture is added slowly to 12 liters of vigorously agitated cold water, and then allowed to separate into layers, The water layer is discarded. The organic layer is mixed with a filtering aid and filtered. The filtrate, 2,835 grams,
- This filtrate then is mixed with 82 grams of water and treated at 50 C. with 87 grams (2.1 equivalents) of zinc oxide over a period of 0.5 hour. To this reaction mixture at 80 C. there is added 88 grams (2.1 equivalents) more of zinc oxide throughout an additional period of 0.5 hour.
- the zinc oxide-treated material is heated at 80 C. for 1 hour, cooled to 49 C., mixed with 783 grams (4.1 equivalents) of a commercial aliphatic primary amine (which has an average molecular weight of 191 in which the aliphatic radical is a mixture of tertiary alkyl radicals containing from 11 to 14 carbon atoms), and heated for 1.5 hours at 90 C.
- the aminetreated material is mixed with 2,634 grams of mineral oil, heated to 135 C./ 10 mm. to remove toluene, mixed with a filtering aid, and filtered. Analyses of the filtrate, a brown liquid, indicate a phosphorus content of 2.7%, a sulfur content of 6.0%, a zinc content of 2.8%, a nitrogen content of 1.2%, and a chlorine content of 5.98%.
- Example 2 A mixture of 667 grams (1 equivalent) of a 50% toluene solution of di-(chlorophenyl)phosphinodithioic acid and 30 grams of Water is heated to 40 C. To the reaction mixture at 40 C. there is added 65 grams 1.1 equivalents) of nickel carbonate whereupon the temperature rises to 50 C. The nickel carbonate treated material is heated at 90 C. for 1.5 hours, then subjected to azeotropic distillation to remove water. To the water-free mixture at 75 C. there is added 191 grams (1 equivalent) of the commercial aliphatic amine described in Example 1. The amine-treated material is heated at 90 C.
- Example 3 12 liters of water over a period of 0.5 hour. The water layer is discarded; the organic layer is mixed with a filtering aid and filtered. The filtrate, 3,006 grams, has an acid number of 87 (phenolphthalein) indicating that the toluene solution contains 4.7 equivalents of di-(isopropylphenyl)phosphinodithioic acid.
- To the mixture at C. there is added an additional 197.5 grams (2.6 equivalents) of cuprous oxide and a temperature rise to C. of the reaction mixture is noted. The cuprous oxide treated material is held at 85 C.
- Example 4 To a mixture of 167 grams (0.25 equivalent) of a 50% toluene solution of di-(chlorophenyl)iphosphinodithioic acid and 167 grams of methanol at 25 C. there is added 10 grams (0.27 equivalent) of calcium hydroxide whereupon the temperature rises to 55 C. The reaction mixture is heated for one hour at 68 C., mixed with 48 grams (0.25 equivalent of the aliphatic amine described in Example 1 at 60 (1., held at 68 C. for 1.5 hours, mixed with 133 grams of mineral oil, heated to 135 C./10 mm., mixed with a filtering aid, and filtered. Analyses of the filtrateindicate a phosphorus content of 2.9%, and a calcium content of 1.3%.
- Example 5 To a mixture of 1,214 grams 13.2 moles) of toluene and 666 grams (3 moles) of P 5 at C. there is added 998 grams (7.5 moles) of aluminum chloride. This mixture is heated at -140 C. for 4 hours, cooled to 25 C. and mixed with 1,668 grams of toluene. The toluene solution is added slowly to 12 liters of vigorously agitated cold water and the Water layer is discarded. The organic layer is mixed with a filtering aid and filtered. The filtrate (2,756 grams) has an acid number of 92 (phenolphthalein) indicating that the toluene solution contains 4.5 equivalents of di-(methylphenyl)phosphinodithioic acid.
- Example 6 To a mixture of 76 grams (0.4 equivalent) of the commercial aliphatic amine described in Example 1 and 198 grams of mineral oil at 400 C. there is added 122 grams (0.4 equivalent) of the zinc salt of dipenylphosphinodithioic acid. The mixture is heated for 3 hours at 90- 100 C., mixed with a filtering aid, and filtered. Analyses of the filtrate, a yellow-brown liquid, indicate a phosphorus content of 2.5%, a sulfur content of 5.6%, a zinc content of 9.7%, and a nitrogen content of 1.6%.
- Example 7 To a mixture of 2,880 grams (24 moles) of isopropyl benzene and 666 grams (3 moles) of P S at 95 C. there is added 998 grams (7.5 moles) of aluminum chloride. The aluminum chloride treated mixture is heated at 115 C. for 7.5 hours (until H 8 evolution is complete), cooled at room temperature and added to 12 liters of vigorously stirred water. The temperature rises to 65 C. The water layer is discarded; the organic layer, 2,977 grams, has an acid number of 77 (phenolphthalein) indicating the presence of four equivalents of di-(isopropylphenyl)-phosphinodithi0ic acid. To the acidic material at 60 C.
- Example 8 To 3,264 grams (4.8 equivalents) of a toluene solution of bis-(trimethylphenyl)phosphinodithioic acid there is added at 5080 C., 204 grams (5.0 equivalents) of zinc oxide. This zinc oxide-treated material is heated for one hour at 80 C., then to 3,216 grams of this mixture at 80 C. there is added 879 grams (4.6 equivalents) of the commercial aliphatic amine described in Example 1. The amine treated material is heated at 90 C. for 1.5 hours, mixed with 2,561 grams of mineral oil, heated to 150 C./ 20 mm., mixed with a filtering aid, and filtered. Analyses of the filtrate, a red liquid, indicate a phosphorus content of 2.6%, a sulfur content of 5.1%, a zinc content of 3.0%, and a nitrogen content of 1.1%.
- Example 9 To 84 grams (0.25 equivalent) of a commercial aliphatic primary amine (which has an average molecular Weight of 330 and in which the aliphatic radical is a mixture of tertiary alkyl radicals containing from 18 to 22 carbon atoms) there is added 102 grams (0.25 equivalent) of the zinc salt (87% pure) of di-(chlorophenyl)phosphinodithioic acid, at a temperature of 40 C. The reaction mixture is heated -for five hours at 95-100" C., then filtered. The filtrate, 146 grams, is mixed with 147 grams of mineral oil and refiltered. Analyses of the refiltered product, a yellow-brown liquid, indicate a phosphorus content of 2.2%, a sulfur content of 4.7%, a zinc content of 2.3%, a nitrogen content of 1.0%, and a chlorine content of 3.3%.
- a commercial aliphatic primary amine which has an average molecular Weight of 330 and in which the alipha
- Example 10 To 1,952 grams (2.28 equivalents) of a 50% toluene solution of the zinc salt of di-(isopropylphenyl)phosphinodithioic acid at 55 C. there is added 298 grams (1.14 equivalent) of dodecylaniline. The reaction mixture is heated for 1.5 hours at 90 C., then at 110 C. to remove water, mixed with a filtering aid, filtered, and heated to 110 C./ 10 mm. Analyses of the residue, a redbrown liquid, indicate a phosphorus content of 5.8%, a sulfur content of 12.1%, a zinc content of 6.8%, and a nitrogen content of 1.4%.
- Example 11 The process of Example 10 is repeated except that ethanolamine (139 grams, 2.28 equivalents) is used in lieu of the dodecylaniline.
- Example 12 The process of Example 10 is repeated except that diiso-propanolamine (304 grams, 2.28 equivalents) is used in lieu of the dodecylaniline.
- Example 13 A mixture of 400 grams (1 equivalent) of the zinc salt (87% pure) of di-(chlorophenyl)phosphinodithioic acid and 150 grams (0.5 equivalent) of a commercial, primary, saturated aliphatic amine having 16 to 17 carbon atoms in the aliphatic radical is ground into a fine powder and added to a mixture of 100 grams (0.52 equivalent) of the commercial aliphatic amine described in Example 1 and 650 grams of mineral oil. The reaction mixture is heated for 3 hours at 137 C. and filtered. Analyses of the filtrate indicate a phosphorus content of 2.6%, a sulfur content of 5.4%, a zinc content of 2.5 a nitrogen content of 1.1%, and a chlorine content of 5.1%.
- Example 14 To 1,244 grams (2 equivalents) of a 50% toluene solution of di-(iso-propylphenyl)phosphinodithioic acid at 60-90 C., there is added 86 grams (2.1 equivalents) of zinc oxide. The zinc oxide-treated material is heated for one hour at C., then mixed with 96 grams (0.5 equivalent) of the commercial aliphatic amine described in Example 1, heated for one hour at 90 C., mixed with 827 grams of mineral oil, heated to 150 C./20 mm., and filtered. Analyses of the filtrate, a green-brown solid at room temperature, indicate a phosphorus content of 3.5%, a sulfur content of 6.9%, a Zinc content of 3.8%, and a nitrogen content of 0.5%.
- Example 15 A mixture of 1,954 grams (13.2 moles) of amylbenzene and 666 grams (3 moles) of P S is heated to C. whereupon 998 grams (7.5 moles) of aluminum chloride is added. The resulting mixture is heated at C. for 5 hours. The mixture is cooled and mixed with 2,340 grams of toluene. The toluene mixture is slowly added to 12 liters of vigorously agitated cold water, and then allowed to separate in layers. The water layer is discarded and the organic layer is filtered. The filtrate, 3,265 grams, has an acid number of 67 (phenolphthalein) indicating that the toluene solution contains 3.9 equivalents of di- (amylphenyl)phosphinodithioic acid.
- Example 16 To 933 grams (1.5 equivalents) of a 50% toluene solution of di (isopropylphenyl)phosphinodithioic acid at 30 C. there is added 61.5 grams (0.55 equivalent) of lead oxide. To the reaction mixture at 50 C. there is added 122.5 grams (1.1 equivalents) more of lead oxide. The reaction mixture is heated at 50 C. for 2 hours. To the reaction mixture at 50 C. there is added 495 grams (1.5 equivalents) of the commercial aliphatic primary amine described in Example 9. The aminetreated reaction mixture is heated at 85 C. for 2 hours, heated to 125 C./ mm., mixed'with 384 grams of mineral diluent oil, mixed with a filtering aid, and filtered. Analyses of the filtered product, a red-brown liquid, indicate a phosphorus content of 2.9%, a sulfur content of 5.4%, a lead content of 6.6%, and a nitrogen content of 1.5%.
- Example 17 To 622 grams (1 equivalent) of a 50% toluene solution of di (isopropylphenyl)phosphinodithioic acid at 30 C. there is added grams (0.27 equivalent) of cobaltic oxide. To the reaction mixture at 50 C. there is added 29 grams (0.53 equivalent) more of cobaltic oxide. The reaction mixture is heated at 85 C. for 2 hours. To the reaction mixture at 70 C. there is added 330 grams (1 equivalent) of the commercial aliphatic primary amine described in Example 9. The amine-treated reaction mixture is heated at 80 C. for 1.5 hours, heated to 125 C./ 15 mm., mixed with 224 grams of mineral diluent oil, mixed with a filtering aid, and filtered. Analyses of the filtrate, a black liquid, indicate a phosphorus content of 3%, a sulfur content of 6.2%, a cobalt content of 2%, and a nitrogen content of 1.5%.
- Example 1 8 cadmium oxide. To the reaction mixture at 50 C. there is added 47 gnams (0.74 equivalent) more of cadmium oxide. The reaction mixture is heated at 85 C. for 2 hours. To the (reaction mixture at 70 C. there is added 330 grams (1 equivalent) of the commercial aliphatic primary amine described in Example 9. The amine-treated reaction mixture is heated at 85 C. for 1.5 hours, heated to 115C./ 10 mm., mixed with a filtering aid and filtered. Analyses of the filtered product, a yellow-brown liquid, indicate a phosphorus content of 4.1%, a sulfur content of 8%, a cadmium content of 8.8%, and a nitrogen content of 2.2%.
- Example 19 To 1,050 grams (1.5 equivalents) of a 50% toluene solution of di (isopropylphenyl)phosphinodithioic acid .at 50 C. there is added 61 grams (1.65 equivalents) of calcium hydroxide. The temperature rises to 77 C.
- Example 9 there is added 330 grams (1 equivalent) of the commercial aliphatic primary amine described in Example 9. The temperature rises to C. (exotherm). The material is held at C. for 1.5 hours and during this time the color of the material changes from violet to green. The product is heated at 125 C./ 10 mm. and then filtered twice. Analysis of the filtered product, a green liquid, indicates a phosphorus content of 2.4%, a sulfur content of 4.4%, a chromium content of 1.29%, and a nitrogen content of 1.0%
- compositions of this invention are useful as additives for lubricating oils.
- the lubricating oils in which the additives of this invention are useful may be of synthetic, animal, vegetable, or mineral origin. Ordinarily, mineral lubricating oils are preferred by reason of their availability, general excellence, and low cost. For certain applications, oils belonging to one of the other three groups may be preferred. For instance, synthetic polyester oils such as didodecyl adipate and di 2 ethylhexyl sebacate are often preferred as jet engine lubricants. Normally the lubricating oils preferred will be fluid oils ranging in viscosity from about 40 Saybolt Universal seconds at 100 F. to about 200 Saybolt Universal seconds at 210 F.
- concentration of the phosphorusand nitrogencontaining compositions of this invention to be used in a lubricant depends primarily upon the type of oil used and the nature of the service to which the lubrication composition is to be subjected. In most instances the concentration will range from about 0.001% to about 5% by weight of a lubricant.
- the lubricating oil compositions of this invention may also contain other additives such as ashless dispersants, metal-containing dispersants, anti-foam agents, colorstabilizers, anti-freeze agents, pour point depressing agents, auxiliary oxidation-inhibiting agents, corrosioninhibiting agent-s, metal-deactivating agents, de-emulsifying agents, extreme pressure improving agents, etc.
- additives such as ashless dispersants, metal-containing dispersants, anti-foam agents, colorstabilizers, anti-freeze agents, pour point depressing agents, auxiliary oxidation-inhibiting agents, corrosioninhibiting agent-s, metal-deactivating agents, de-emulsifying agents, extreme pressure improving agents, etc.
- compositions of this invention are used in combination with phenyl beta-naphthylamjne in a lubricating oil,-an unusual oxidation inhibiting effect is noted.
- Detergents useful in conjunction with the phosphorusand nitrogen-containing compositions of this invention in lubricants include normal or basic salts of petroleum naphtheni-c. acids, petroleum sulfonic acids, oil-soluble fatty acids, ashless detergents such as the reaction prodnot of triethylene tetramine with an alkenyl substituted succinic anhydride having at least 50 carbon atoms in the alkenyl substituent, and a copolymer of 5 parts of betadiethyl aminoethyl acrylate with parts of dodecyl methacrylate, etc.
- Others include barium mahogany sulfo'nate, the barium salt of the phosphorus acids obtained by the reaction of'polyisobutene (molecular weight of 1000) with phosphorus pentasulfide, and the calcium salt of didodecyl benzene sulfonate.
- Anti-foam agents include polymeric alkyl siloxanes, poly(.a1kyl methaorylates) and a condensation product of alkyl phenol with formaldehyde and an amine. Pour point depressing agents are illustrated by polymers of ethylene, propylene, or isobutene ,and poly(alkyl methacrylates). Corrosionand oxidation-inhibiting agents include 4 methyl 2,6, di tert butylphenol, N,N' sec butyl phenylene diamine, basic metal petroleum sulfates, metal phenates, amines, benzylthiocyanates, etc.
- Film strength agents include, e.g., chlorinated paraflin oils containing from 20 to 70% of chlorine, chlorinated eicosane wax .containing from 50 to 60% of chlorine, hexachloro-distearic acids, sulfurized sperm oil, sperm oil, corn oil, etc.
- Viscosity index irnprovers include, e.g., polymerized and copolymerized alkyl methacry-lates, polymerized butene, etc.
- compositions of this invention may simply be added to the oil at the appropriate concentration.
- a concentrate of the additive is prepared by dissolving it in a limited amount of the oil, optionally with other additives, and the concentrate is then diluted with additional amounts of the oil to prepare the final oil composition.
- the following lubricants are set forth for the purpose of illustration. All percentages are by weight.
- Example B Mineral lubricating oil having a viscosity of 99 SUS (Saybolt Universal seconds) at 100 F. to 39 SUS at 210 F. and viscosity index of 93 89.0 Neutral barium salt of the steam hydrolyzed reaction product of polyisobutene (molecular weight of 48,000) with phosphorus pentasulfide 7.0 Carbonated, basic barium salt of sperm oil acid 1.5 Product of Example 1 2.0 Polymeric alky-l acrylate VI improver and pour point depressant 0.48 Polymeric alkyl siloxane anti-foam agent 0.02
- Example C Synthetic polyester lubricating oil (trimethylolpropane ester of a C carboxylic acid) having a viscosity of 115 SUS at 100 F. to 42.4 SUS at 210
- Example F Synthetic polyester lubricating oil described in Example C 93.5 Phenyl beta-naphthylamine 3.0 Product of Example 1 3.5
- Example G SAE 20 mineral lubricating oil 96.0 Phenyl beta-naphthylamine 0.01 Product of Example 7 3.49
- Example J Mineral oil as described in Example B 95.0 Carbonated, basic barium salt of phosphorus trichlo- 12 ride and chlorinated polyisobutene (100,000 molecular weight) Tetraethylene pentamine acylated with a substituted succinic anhydride having a polyisobutenyl radical Tetraethylene pentamine acylated with a substituted succinic anhydride having a polyisobutenyl radical having (molecular weight of 850) as substituent 2.5
- Example L SAE 20 mineral lubricating oil 92 Tetraethylene pentamine acylated with a substituted succinic anhydride having a polyisobutenyl radical (molecular weight of 850) as substituent 3
- Product of Example 2 5 The compositions of this invention are useful for improving the wear properties of lubricating oils, when incorporated therein in additive quantities.
- the wear properties of a lubricant are measured by the Four Ball Wear test. In this test, four /2" diameter SAE 52100 steel balls are arranged in a tetrahedral formation and the top ball is made to rotate against the three bottom balls, the points of contact being lubricated by the test lubricant.
- the top ball is rotated at 600 rpm, loaded against the three bottom balls with a 40 kilogram weight, for a period of 2 hours.
- the lubricating oil and steel balls are maintained at a temperature of 200 F.
- the steel balls are examined for wear, evidenced by circular scars at the indicated points of contact. The diameter of these scars is measured and reported as an average.
- the lubricant of Example B allows an average scar diameter of 0.40 mm.
- a lubricant identical with Example B except that it does not contain the product of Example 1 allows an average scar diameter of 0.79 mm. This comparison indicates that the compositions of this invention are good anti-wear agents for lubricating oils.
- the lubricant composition of Example B is further useful as an automatic transmission fluid; this is illustrated by its performance in the Chevrolet Powerglide Oxidation Test, CRC Designation L39.
- This test consists of operating a Chevrolet passenger car Powerglide Transmission for 300 hours under the following conditions: transmission sump temperature, 275 F.; governor pressure, 55-70 p.s.i.; main line pressure, 95 p.s.i.; transmission speed, 1750-1800 r.p.m.
- This test is regarded in the industry as an important means for evaluating lubricating compositions for use in automatic transmissions.
- the lubricant is evaluated in terms of (1) the weight loss of the cindered bronze thrust washer due to corrosion, (2) the amounts of varnish and sludge formed on the clutch plates (expressed in terms of a numerical rating between 10, representing no varnish or sludge, and 0, representing maximum varnish or sludge) and (3) the amount of the overall varnish and sludge formed in the transmission (expressed as a numerical rating between 50, representing no varnish or sludge, and 0, representing a maximum amount of sludge or varnish).
- Example B The lubricant composition of Example B passes this test in all respects with a 0.12% weight loss of the cindered bronze thrust washer, a clutch plate varnish rating of 10, a clutch plate sludge rating of 9.7, an overall varnish rating of 50, and an overall sludge rating of 48.
- compositions of this invention in synthetic lubricating oils are illustrated by the performance of particular lubricants in a severe oxidation test, a modification of the procedure indicated in MIL-L-6808D.
- air is bubbled 13 through a 250-ml. sample of the test oil at 425 F. containing 1" x 1" x 0.032" panels of copper, titanium, silver, aluminum, and steel for 40 hours at a rate of 3.4 cu. ft./hr.
- the neutralization number of the oil sample is determined before and after the test according to ASTM designation D974-58T using alpha-naphthalbenzein indicator.
- Oil sample losses are measured at 5-hour intervals and the tested oil is replenished with fresh test oil sample.
- the percent increase of the viscosity of the test oil sample is also determined at 5-hour intervals and the weight loss of the metal samples determined at the end of the test.
- the lubricants of Examples C and D when subjected to this test show the following:
- compositions of this invention are useful oxidation inhibitors for synthetic polyester oils.
- results also indicate that the compositions of this invention act synergistically with phenyl beta-naphthylamine as oxidation inhibitors in synthetic polyester oils.
- the synergism is indicated for lubricant compositions wherein from about 0.001 to about 5% by weight of a composition of this invention and from about 0.001 to about 5% by weight of phenyl beta-naphthylamine are incorporated.
- Lubricant compositions containing from about 1% to about 5% by weight of a composition of this invention and from about 0.5% to about 3% of phenyl beta-naphthylamine are preferred, since maximum oxidation inhibition is obtained from the combination when these limits are employed.
- compositions of this invention have utility as additives in lubricating oils, they are also useful for other purposes.
- small amounts of the composition of this invention may be incorporated in gasolines and fuel oils as stabilizers or into paint films as oxidation inhibitors.
- Compositions of this invention are also useful as insecticides.
- An oil soluble nitrogenand phosphorus-containing composition having the general formula R S A J! wherein R is an aryl or halogen-substituted aryl radical, or an alkaryl radical containing from 7 to about 26 carbon atoms; each of A and B is hydrogen or an aliphatic hydrocarbon radical; M is zinc, calcium, copper, nickel, cobalt, chromium, lead or cadmium; x is the valence of M; and y is from about 0.5 to about 6.
- composition of claim 2 wherein contains from 1 to about 40 carbon atoms, at least one of A and B is an aliphatic hydrocarbon radical, and y is 1 or 2.
- composition of claim 5 wherein R is a chlorophenyl radical; y is 2; A is hydrogen and B is a tertiary alkyl radical containing from 8 to 30 carbon atoms.
- R is an isopropylphenyl radical; y is 2; A is hydrogen and B is a tertiary alkyl radical containing from 8 to 30 carbon atoms.
Description
United States Patent 3,351,647 NITROGEN, PHOSPHORUS AND METAL CONTAINING COMPOSITION Thomas A. Butler and Herbert F. Wiese, Cleveland, Ohio,
assignors to The Lubrizol Corporation, Wickliife, Ohio,
a corporation of Ohio No Drawing. Filed May 14, 1963, Ser. No. 280,452 7 Claims. (Cl. 260-4293) ABSTRACT OF THE DISCLOSURE Phosphorusand nitrogen-containing compositions are prepared by reacting a metal salt of a phosphinodithioic acid, especially a zinc salt of a diarylphosphinodithioic acid, with an amine, especially an aliphatic amine having from one to about 40 carbon atoms. The compositions are useful as additives for lubricating oils and automatic transmission fluids, in which they act as oxidation inhibitors and anti-wear agents. They afford synergistic oxidation inhibition properties when used with phenyl beta-naphthylamine.
This invention relates to novel compositions which are suitable for use as additives in lubricating compositions and more particularly it relates to a new class of compositions which are effective to inhibit oxidation in lubricating compositions and prevent wear of the metal surfaces being lubricated.
It is known that when oils, such as conventional lubricating oils, are subjected to extended periods of use, especially at high operating temperatures, they tend to decompose and form complex and objectionable oxidation and decomposition products including peroxides and organic acids. These substances possess corrosive and other deleterious properties and, unless neutralized or counteracted, will attack and damage engine metallic parts. These acids, furthermore, may go through a chemical process whereby the molecules combine or polymerize into large aggregates to form lacquer-like deposits on or between the moving parts of the engine, causing excessive wearing or even sticking of operating parts. Even larger quantities of polymerization products remain dispersed in the partially oxidized oil and are readily precipitated to form a sludge when the engine cools or when the fresh oil is added to the engine. These precipitated sludges become caked on the heated metal surfaces and reduce the effective life of the engine by preventing proper functioning of the parts thereof, such as by gumming up the piston rings which prevents proper piston action, or by blocking the oil passages of small diameter through which the lubricating oil nonmally flows to the bearings, whereby bearing failures are caused.
Elminating or minimizing the above effects on oils and engines has constituted a lubricating problem since the advent of the internal combustion engine and many proposals for its solution appear in the prior art. These proposed solutions include use of the more stable synthetic ester oils and inclusion of addition agents, commonly called antioxidants, in conventional and synthetic oils to impart antioxidation properties thereto. Within recent years, however, more effective means have been required to solve the problem in many instances.
In the automotive industry, for example, reducing oil reservoir size, removing cooling coils, replacing metal gears with plastic gears, and warranting extended service periods, viz., requiring oil changes upon every 6,000 miles of driving in contrast to the former 1,000 mile standard, are factors which have increased the severity and complexity of the aforesaid problem. Automatic transmission 3,351,647 Patented Nov. 7, 1967 fluids, for example, are subjected to higher temperatures, increased air contact, and longer service periods.
Likewise, in the lubrication of jet turbine bearings, the design of more powerful turbines has led to an increase in the lubricant reservoir temperature and to greater difficulty in maintaining lubricant stability under the more severe conditions. For example, a lubricant which will operate satisfactorily at a reservoir temperature of 250 F. may sludge badly, build up viscosity, develop high acidity, and corrode metals at a reservoir temperature at 400 F.
Among the objects of this invention, therefore, is that of providing new chemical compositions useful as antioxidants.
Another object of this invention is to provide methods of preparing these new chemical compounds.
Another object of this invention is to provide additives for lubricating compositions.
Still another object of this invention is to provide new lubricating compositions.
These and other objects are achieved by providing a phosphorusand nitrogen-containing composition having the general formula wherein R is a substantially hydrocarbon radical; M is a metal selected from the group consisting of zinc, calcium, copper, nickel, cobalt, chromium, lead, and cadmium; A, B, and C are radicals selected from the class consisting of hydrogen and substantially hydrocarbon radicals; x is the valence of M; y is from about 0.5 to about 6.
The R radicals of the nitrogenand phosphorus-containing compositions of this invention may be the same or different radicals including alkyl, aryl, aralkyl, alkaryl, cycloalkyl, and heterocyclic radical, as well as such radicals containing substitutents such as halogen, nitro, and the like. For reasons of economy and thermal stability, the aryl and alkaryl radicals are preferred, especially alkaryl radicals containing from 7 to about 26 carbon atoms.
A, B, and C of the nitrogenand phosphorous-containing compositions may be hydrogen or a substantially hydrocarbon radical. Substantially hydrocarbon radicals represented by A, B, and C include alkyl, alkylol, aryl, aralkyl, alkaryl, cycloalkyl, aminoalkyl, and polyaminopolyalkene. These hydrocarbon radicals may contain from 1 to about 40 carbon atoms. However, where oilsolubility is a criterion, preferably, A and B are hydrogen radicals and C is an aliphatic radical containing at least about 12 carbon atoms.
The value of y may range from about 0.5 to about 6 and preferably is within the range of from about 1 to about the valence of the metal (M), i.e., x. The exact chemical structure of the composition is not known.
In the paragraphs to follow, reference is made to equivalent weights of reactants used in processes to provide the compositions of this invention. The term equivalent is based upon a consideration of the number of functional groups in a reactant, i.e., if there are two functional groups, then the equivalent weight is one-half the molecular weight. For the purposes of this specification, an equivalent weight of an amine will be that weight of amine containing one atomic weight of nitrogen and an equivalent weight of a phosphinodithioic acid or metal salt thereof will be that weight of phosphinodithioic acid or metal salt thereof containing one atomic weight of phosphorus.
The compositions of this invention may be prepared by reacting the metal salt of a phosphinodithioic acid ,with an amine. The indicated reaction between the amine and the metal salt is often exothermic and may be carried out in many cases simply by mixing the reactants at room temperature. It is preferred to carry out the reaction at a temperature from about 10 C. to about 150 C.
The use of a solvent for the reaction mixture is contemplated and sometimes is especially advantageous.
The novel compositions of this invention may be prepared, alternatively, by first forming a complex of the inorganic metal component with ammonia or an amine, followed by a double decomposition reaction of this inorganic metal complex with the sodium or potassium salt of a phosphinodithioic acid. For example, a complexforming metallic salt, such as zinc sulfate, may be reacted with ammonium hydroxide to form zinc ammonium sulfate; this is further reacted with the sodium salt of diphenyl phosphinodithioic acid to form a composition of this invention. Although the latter method is quite satisfactory in some instances, the former method is preferred.
The metal salt reactants employed as above for producing compositions of this invention are derivatives of phosphinodithioic acids conforming to the general formula wherein R is a substantially hydrocarbon radical. The R groups of the phosphinodithioic acid may be the same or different radicals including alkyl, aryl, aralkyl, alkaryl, cycloalkyl, and heterocyclic radicals, as well as such radicals containing substituents such as halogen, nitro, and the like. For reasons of economy and thermal stability, aryl and alkaryl radicals are preferred.
The phosphinodithioic acids may be prepared by the reaction of Grignard reagents with phosphorus pentasulfide (see Organo Phosphorus Compounds, G. M. Kosolapofi, p. 135, John Wiley and Son, New York, 1950). The preferred and more economical method for preparing the phosphinodithioic acid is that described in US. 2,797,238 wherein aromatic compounds having ionization constants less than 1 10- in water at 25 C. and having at least one hydrogen atom attached to an aromatic ring structure are reacted with P 5 in the presence of AlCl in amounts such that the ratio of moles of AlCl to moles of P 8 is at least one. The preparation of alkyl aryl phosphinodithioic acids is accomplished by the reaction of an alkyl thiophosphine sulfide with an aromatic compound in the presence of aluminum chloride (see description by Newallis et al. in vol. 27, Journal of Organic Chemistry, page 3829).
Examples of aromatic radicals are organic radicals containing at least one resonant ring structure, such as phenyl, naphthyl, anthracyl, phenanthryl, naphthacyl, crysyl, pyryl, tribenzyl, biphenyl, and terphenyl radicals, and the substitution products of these such as their alkylation products, halogenation products, nitration products, etc. Examples of the alkylation products include tolyl, xylyl, di-ethylphenyl, iso-propylphenyl, n-propylphenyl, tert-butylphenyl, di-tert-butylphenyl, iso-butylphenyl, r1- butylphenyl, tert-amylphenyl, cyclohexylphenyl, methylcyclohexylphenyl, caprylphenyl, diisobutylphenyl, dioctylphenyl, laurylphenyl, cetylphenyl, parafiin wax substituted phenyl, dodecylphenyl, di-dodecylphenyl, etc. Examples of halogenation products include chlorophenyl, 2,6 dichlorophenyl, trichlorophenyl, 4 bromophenyl, monoand poly-chloroxenyl, monoand poly-chloronaphthyl, monoand poly-chloroanthracyl, methyl chlorophenyl, ethyl chlorophenyl, ethyl chloroanthracyl, etc. Examples of nitro product include nitrophenyl, nitroxenyl, methyl-nitrophenyl, butyl-nitrophenyl, etc.
The salts of the organic phosphinodithioic acids used in preparing the novel compositions of this invention can be prepared by the usual salt forming reactions. These include the reaction of an organic phosphinodithioic acid with a metal powder, a metal hydroxide or metal oxide and the double decomposition reaction of the sodium or potassium salt of an organic phosphinodithioic acid with a metal halide or other suitable metal salt. The metals which may be used in accordance with the principle of this invention include zinc, calcium, copper, nickel, cobalt, chromium, lead, and cadmium. These metals may be incorporated in salts by direct reaction of a phosphinodithioi-c acid with, for example, zinc oxide, zinc hydroxide, calcium hydroxide, cuprous oxide, cupric oxide, nickel carbonate, cobaltous carbonate, or lead oxide, or by the double decomposition reaction of a sodium or potassium salt of a phosphinodithioic acid with, for example, cobaltous chloride, cobaltous nitrate, chromic nitrate, or chromous acetate.
Alternatively, in the case of certain zinc salts, the method described in US. 2,809,979 may be employed, wherein a mixture of aromatic compounds selected from the class consisting of aromatic hydrocarbons and halogenated aromatic hydrocarbons, phosphorus pentasulfide, an aluminum halide selected from the class consisting of aluminum chloride and aluminum bromide, and a Zinc halide selected from the class consisting of Zinc chloride and zinc bromide, is heated at a temperature within the range of about 130 C. to about 250 C.
Ammonia and many amines may be used to form the nitrogen and phosphorus-containing compositions of this invention. Broadly, the N-containing reactants useful in producing the compositions of this invention conform for the most part to the structural formula wherein A, B, and C are radicals selected from the class consisting of hydrogen, alkyl, alkylol, aryl, aralkyl, alkaryl, cycloalkyl, aminoalkyl, and polyaminopolyalkylene. It will be appreciated that two of A, B, and C may be a single polyalkylene radical containing up to 5 carbon atoms. Preferably, at least one of A, B, and C is a hydrogen radical. This includes, for example, aliphatic amines, aromatic amines, polyamines, cyclo-aliphatic amines, heterocyclic amines, and carbocyclic amines. Specific examples of useful N-containing reactants include ammonia, ethylamine, propylamine, isopropylamine, butylamine, cyclohexylamine, n-hexylamine, dodecylamine, didodecylamine, tridodecylamine, N-methyl octylamine, N-dodecyltrimethylene diamine, ethanolamine, triethanolamine, guanidine, tripropylamine, aniline, o-toluidine, benzidine, phenylenediamine, N,N li-sec-butylphenylene diamine, beta-naphthylamine, alpha-naphthylamine, morpholine, piperazine, methane diamine, cyclopentylamine, ethylene diamine, hexamethylene tetramine, octamethylene diamine, and N,N-dibutylphenylene diamine.
Aliphatic amines having from one to about 40 carbon atoms are preferred for the purposes of this invention. The preference is based largely upon the availability as well as the general compatibility with hydrocarbon materials, such as lubricating oils, paints, and fuels of the compositions of this invention derived from such amines. Examples of such aliphatic amines include tetracontylamine, tricontylamine, N heptylhexylamine, methylethyl-i propylamine, tirethylamine, octanol amine, and tripropanol amine. Especially useful in this sense are the tertiary alkyl primary amines containing from about 10 to about carbon atoms.
Where oil-solubility of the novel compositions of this invention is required, primary aliphatic amines having more than about 12 carbon atoms are preferred, e.g., tert-dodecylamine, tert-octadecylamine, behenylamine, stearylamine, docosanylamine, hexacontanylamine, and pentahexacontanylamine.
Examples of useful compositions of this invention include the complexes of one equivalent of tert-dodecyl amine with one equivalent of the zinc salt of di-xylylphosphinodithioic acid; one equivalent of tert-octadecylamine with one equivalent of the calcium salt of bis-(dichlorophenyl)phosphinodithioic acid; one equivalent of propylamine with one equivalent of the cadmium salt of di- (octylphenyl)phosphinodithioic acid; one equivalent of aniline with one equivalent of the cupric salt of di-(pentylphenyl)phosphinodithioic acid; two equivalents of ethylene diamine with the one equivalent of the cobaltic salt of di-(octylnaphthyl)phosphinodithioic acid; one equivalent of tert-dodecylamine with one equivalent of the zinc salt of chlorophenyl isopropylphenylphosphinodithioic acid; one equivalent of pentahexacontylamine with one equivalent of the lead salt of di-(isopropylphenyl)- phosphinodithioic acid; one equivalent of cyclohexylamine with one equivalent of the nickel salt of di-(ethylphenyl)- phosphinodithioic acid; one equivalent of hexacontylamine with one equivalent of the cuprous salt of di-tolylphosphinodithioic acid; two equivalents of propylamine with one equivalent of the chromous salt of di-(octylphenyl)phosphinodithioic acid; three equivalents of ethylene diamine with one equivalent of the cobaltous salt of di-(octylnaphthyl)phosphinodithioic acid; one equivalent of docosenyl amine with one equivalent of the zinc salt of diphenylphosphinodithioic acid; one equivalent of tert-octadecyl amine with one equivalent of the zinc salt of di-(phenylthiophenyl)phosphinodithioic acid; one equivalent of stearyl amine with one equivalent of the zinc salt of di-(chlorophenyl)phosphinodithioic acid; one equivalent of docosanylamine with one equivalent of the zinc salt of di-(pentylphenyl)phosphinodithioic acid; one equivalent of ethanolamine with one equivalent of the zinc salt of di-(pentylphenyl)phosphinodithioic acid; and one equivalent of tridodecyl amine with one equivalent of the zinc salt of di-(pentylphenyl)phosphinodithioic acid.
The complexes or reaction products of this invention are, for the most part, quite readily soluble in hydrocarbon liquids such as toluene, xylene, heptane, and hexane. In fact, in many cases it is desirable to form the compounds of this invention in liquid hydrocarbon media.
Various specific embodiments of the invention as broadly defined above are included hereinafter for purposes of illustration only, and are not to be construed as limiting the invention in any way. All parts and percentages are by weight unless otherwise specified.
Example 1 A mixture of 1,485 grams (13.2 moles) of chlorobenzene and 666 grams (3 moles) of P 8 is heated to 100 C. in 0.5 hour whereupon 998 grams (7.5 moles) of aluminum chloride is added. The resulting mixture is refluxed at 145 C. for 0.5 hour and then heated for 4 hours at 160-165 C. The product mixture is cooled and mixed with 1,914 grams of toluene. The toluene mixture is added slowly to 12 liters of vigorously agitated cold water, and then allowed to separate into layers, The water layer is discarded. The organic layer is mixed with a filtering aid and filtered. The filtrate, 2,835 grams,
has an acid number of 81 (phenolphthalein) indicating that the toluene solution contains 4.1 equivalents of di- (chlorophenyl)phosphinodithioic acid.
, This filtrate then is mixed with 82 grams of water and treated at 50 C. with 87 grams (2.1 equivalents) of zinc oxide over a period of 0.5 hour. To this reaction mixture at 80 C. there is added 88 grams (2.1 equivalents) more of zinc oxide throughout an additional period of 0.5 hour. The zinc oxide-treated material is heated at 80 C. for 1 hour, cooled to 49 C., mixed with 783 grams (4.1 equivalents) of a commercial aliphatic primary amine (which has an average molecular weight of 191 in which the aliphatic radical is a mixture of tertiary alkyl radicals containing from 11 to 14 carbon atoms), and heated for 1.5 hours at 90 C. The aminetreated material is mixed with 2,634 grams of mineral oil, heated to 135 C./ 10 mm. to remove toluene, mixed with a filtering aid, and filtered. Analyses of the filtrate, a brown liquid, indicate a phosphorus content of 2.7%, a sulfur content of 6.0%, a zinc content of 2.8%, a nitrogen content of 1.2%, and a chlorine content of 5.98%.
Example 2 A mixture of 667 grams (1 equivalent) of a 50% toluene solution of di-(chlorophenyl)phosphinodithioic acid and 30 grams of Water is heated to 40 C. To the reaction mixture at 40 C. there is added 65 grams 1.1 equivalents) of nickel carbonate whereupon the temperature rises to 50 C. The nickel carbonate treated material is heated at 90 C. for 1.5 hours, then subjected to azeotropic distillation to remove water. To the water-free mixture at 75 C. there is added 191 grams (1 equivalent) of the commercial aliphatic amine described in Example 1. The amine-treated material is heated at 90 C. for 1.5 hours, mixed with 377 grams of mineral oil, heated to 135 C./l0 mm., mixed with a filtering aid, and filtered. Analyses of the filtrate, a red-brown liquid, indicate a phosphorus content of 2.6%, a sulfur content of 6.0%, a nickel content of 2.4%, and a chlorine content of 4.1%.
Example 3 12 liters of water over a period of 0.5 hour. The water layer is discarded; the organic layer is mixed with a filtering aid and filtered. The filtrate, 3,006 grams, has an acid number of 87 (phenolphthalein) indicating that the toluene solution contains 4.7 equivalents of di-(isopropylphenyl)phosphinodithioic acid. To the toluene solution at 50 C. there is added 197.5 grams (2.6 equivalents) of cuprous oxide. To the mixture at C. there is added an additional 197.5 grams (2.6 equivalents) of cuprous oxide and a temperature rise to C. of the reaction mixture is noted. The cuprous oxide treated material is held at 85 C. for 1 hour, cooled to 50 (3., mixed with 898 grams (4.7 equivalents) of the commercial aliphatic amine described in Example 1, heated to C. for 1.5 hours, mixed with 2,766 grams of mineral oil, heated to 150 C./ 10 mm., mixed with a filtering aid, and filtered. Analyses of the filtrate indicate a phosphorus content of 1.7%, a sulfur content of 3.3%, a copper content of 3.7%, and a nitrogen content of 1.2%.
Example 4 To a mixture of 167 grams (0.25 equivalent) of a 50% toluene solution of di-(chlorophenyl)iphosphinodithioic acid and 167 grams of methanol at 25 C. there is added 10 grams (0.27 equivalent) of calcium hydroxide whereupon the temperature rises to 55 C. The reaction mixture is heated for one hour at 68 C., mixed with 48 grams (0.25 equivalent of the aliphatic amine described in Example 1 at 60 (1., held at 68 C. for 1.5 hours, mixed with 133 grams of mineral oil, heated to 135 C./10 mm., mixed with a filtering aid, and filtered. Analyses of the filtrateindicate a phosphorus content of 2.9%, and a calcium content of 1.3%.
Example 5 To a mixture of 1,214 grams 13.2 moles) of toluene and 666 grams (3 moles) of P 5 at C. there is added 998 grams (7.5 moles) of aluminum chloride. This mixture is heated at -140 C. for 4 hours, cooled to 25 C. and mixed with 1,668 grams of toluene. The toluene solution is added slowly to 12 liters of vigorously agitated cold water and the Water layer is discarded. The organic layer is mixed with a filtering aid and filtered. The filtrate (2,756 grams) has an acid number of 92 (phenolphthalein) indicating that the toluene solution contains 4.5 equivalents of di-(methylphenyl)phosphinodithioic acid. To the toluene solution at 50 C. there is added over a period of 0.5 hour, 95.5 grams (2.35 equivalents) of zinc oxide, and then an additional 95.5 grams (2.35 equivalents) of zinc oxide is added at 80 C. The zinc oxide treated material is heated at 85 C. for 1.5 hours, cooled to 60 C., mixed with 860 grams (4.5 equivalents) of the commercial aliphatic amine described in Example 1, heated for 1.5 hours at 90 C., mixed with 2,596 grams of mineral oil, heated to 135 C./ 10 mm., mixed with a filtering aid, and filtered. Analyses of the filtrate, a reddish brown liquid, indicate a phosphorus content of 2.9%, a sulfur content of 6.3%, a zinc content of 2.9%, and a nitrogen content of 1.2%.
Example 6 To a mixture of 76 grams (0.4 equivalent) of the commercial aliphatic amine described in Example 1 and 198 grams of mineral oil at 400 C. there is added 122 grams (0.4 equivalent) of the zinc salt of dipenylphosphinodithioic acid. The mixture is heated for 3 hours at 90- 100 C., mixed with a filtering aid, and filtered. Analyses of the filtrate, a yellow-brown liquid, indicate a phosphorus content of 2.5%, a sulfur content of 5.6%, a zinc content of 9.7%, and a nitrogen content of 1.6%.
Example 7 To a mixture of 2,880 grams (24 moles) of isopropyl benzene and 666 grams (3 moles) of P S at 95 C. there is added 998 grams (7.5 moles) of aluminum chloride. The aluminum chloride treated mixture is heated at 115 C. for 7.5 hours (until H 8 evolution is complete), cooled at room temperature and added to 12 liters of vigorously stirred water. The temperature rises to 65 C. The water layer is discarded; the organic layer, 2,977 grams, has an acid number of 77 (phenolphthalein) indicating the presence of four equivalents of di-(isopropylphenyl)-phosphinodithi0ic acid. To the acidic material at 60 C. there is added 171 grams (4.2 equivalents) of zinc oxide. The zinc oxide treated material is heated at 80 C. for 1 hour, cooled to 60 C., mixed with 764 grams (4.0 equivalents) of the commercial aliphatic amine described in Example 1, heated at 90 C., held for 1.5 hours at 90 C,. mixed with 2,227 grams of mineral oil, heated to 150 C./ mm., mixed with a filtering aid, and filtered. Analyses of the filtrate, a yellow-brown liquid, indicates a phosphorus content of 3.1%, a sulfur content of 6.2%, a zine content of 2.4%, and a nitrogen content of 1.0%.
Example 8 To 3,264 grams (4.8 equivalents) of a toluene solution of bis-(trimethylphenyl)phosphinodithioic acid there is added at 5080 C., 204 grams (5.0 equivalents) of zinc oxide. This zinc oxide-treated material is heated for one hour at 80 C., then to 3,216 grams of this mixture at 80 C. there is added 879 grams (4.6 equivalents) of the commercial aliphatic amine described in Example 1. The amine treated material is heated at 90 C. for 1.5 hours, mixed with 2,561 grams of mineral oil, heated to 150 C./ 20 mm., mixed with a filtering aid, and filtered. Analyses of the filtrate, a red liquid, indicate a phosphorus content of 2.6%, a sulfur content of 5.1%, a zinc content of 3.0%, and a nitrogen content of 1.1%.
Example 9 To 84 grams (0.25 equivalent) of a commercial aliphatic primary amine (which has an average molecular Weight of 330 and in which the aliphatic radical is a mixture of tertiary alkyl radicals containing from 18 to 22 carbon atoms) there is added 102 grams (0.25 equivalent) of the zinc salt (87% pure) of di-(chlorophenyl)phosphinodithioic acid, at a temperature of 40 C. The reaction mixture is heated -for five hours at 95-100" C., then filtered. The filtrate, 146 grams, is mixed with 147 grams of mineral oil and refiltered. Analyses of the refiltered product, a yellow-brown liquid, indicate a phosphorus content of 2.2%, a sulfur content of 4.7%, a zinc content of 2.3%, a nitrogen content of 1.0%, and a chlorine content of 3.3%.
Example 10 To 1,952 grams (2.28 equivalents) of a 50% toluene solution of the zinc salt of di-(isopropylphenyl)phosphinodithioic acid at 55 C. there is added 298 grams (1.14 equivalent) of dodecylaniline. The reaction mixture is heated for 1.5 hours at 90 C., then at 110 C. to remove water, mixed with a filtering aid, filtered, and heated to 110 C./ 10 mm. Analyses of the residue, a redbrown liquid, indicate a phosphorus content of 5.8%, a sulfur content of 12.1%, a zinc content of 6.8%, and a nitrogen content of 1.4%.
Example 11 The process of Example 10 is repeated except that ethanolamine (139 grams, 2.28 equivalents) is used in lieu of the dodecylaniline.
Example 12 The process of Example 10 is repeated except that diiso-propanolamine (304 grams, 2.28 equivalents) is used in lieu of the dodecylaniline.
Example 13 A mixture of 400 grams (1 equivalent) of the zinc salt (87% pure) of di-(chlorophenyl)phosphinodithioic acid and 150 grams (0.5 equivalent) of a commercial, primary, saturated aliphatic amine having 16 to 17 carbon atoms in the aliphatic radical is ground into a fine powder and added to a mixture of 100 grams (0.52 equivalent) of the commercial aliphatic amine described in Example 1 and 650 grams of mineral oil. The reaction mixture is heated for 3 hours at 137 C. and filtered. Analyses of the filtrate indicate a phosphorus content of 2.6%, a sulfur content of 5.4%, a zinc content of 2.5 a nitrogen content of 1.1%, and a chlorine content of 5.1%.
Example 14 To 1,244 grams (2 equivalents) of a 50% toluene solution of di-(iso-propylphenyl)phosphinodithioic acid at 60-90 C., there is added 86 grams (2.1 equivalents) of zinc oxide. The zinc oxide-treated material is heated for one hour at C., then mixed with 96 grams (0.5 equivalent) of the commercial aliphatic amine described in Example 1, heated for one hour at 90 C., mixed with 827 grams of mineral oil, heated to 150 C./20 mm., and filtered. Analyses of the filtrate, a green-brown solid at room temperature, indicate a phosphorus content of 3.5%, a sulfur content of 6.9%, a Zinc content of 3.8%, and a nitrogen content of 0.5%.
Example 15 A mixture of 1,954 grams (13.2 moles) of amylbenzene and 666 grams (3 moles) of P S is heated to C. whereupon 998 grams (7.5 moles) of aluminum chloride is added. The resulting mixture is heated at C. for 5 hours. The mixture is cooled and mixed with 2,340 grams of toluene. The toluene mixture is slowly added to 12 liters of vigorously agitated cold water, and then allowed to separate in layers. The water layer is discarded and the organic layer is filtered. The filtrate, 3,265 grams, has an acid number of 67 (phenolphthalein) indicating that the toluene solution contains 3.9 equivalents of di- (amylphenyl)phosphinodithioic acid. To the filtrate (toluene solution) at 50-80 C., there is added 167 grams (4.1 equivalents) of zinc oxide. The zinc oxide treated material is heated at 80 C. for one hour, mixed with 2,017 grams of mineral oil, further diluted with 250 grams of toluene, mixed with 372 grams (1.95 equivalents) of the commercial aliphatic amine described in Example 1, heated at 90 C. for 1.5 hours, then heated to C./ 20 mm., and filtered. Analyses of the filtrate, a red-brown liquid, indicate a phosphorus content of 3.2%, a sulfur content of 5.6%, a zinc content of 2.3%, and a nitrogen content of 0.7%.
Example 16 To 933 grams (1.5 equivalents) of a 50% toluene solution of di (isopropylphenyl)phosphinodithioic acid at 30 C. there is added 61.5 grams (0.55 equivalent) of lead oxide. To the reaction mixture at 50 C. there is added 122.5 grams (1.1 equivalents) more of lead oxide. The reaction mixture is heated at 50 C. for 2 hours. To the reaction mixture at 50 C. there is added 495 grams (1.5 equivalents) of the commercial aliphatic primary amine described in Example 9. The aminetreated reaction mixture is heated at 85 C. for 2 hours, heated to 125 C./ mm., mixed'with 384 grams of mineral diluent oil, mixed with a filtering aid, and filtered. Analyses of the filtered product, a red-brown liquid, indicate a phosphorus content of 2.9%, a sulfur content of 5.4%, a lead content of 6.6%, and a nitrogen content of 1.5%.
' Example 17 To 622 grams (1 equivalent) of a 50% toluene solution of di (isopropylphenyl)phosphinodithioic acid at 30 C. there is added grams (0.27 equivalent) of cobaltic oxide. To the reaction mixture at 50 C. there is added 29 grams (0.53 equivalent) more of cobaltic oxide. The reaction mixture is heated at 85 C. for 2 hours. To the reaction mixture at 70 C. there is added 330 grams (1 equivalent) of the commercial aliphatic primary amine described in Example 9. The amine-treated reaction mixture is heated at 80 C. for 1.5 hours, heated to 125 C./ 15 mm., mixed with 224 grams of mineral diluent oil, mixed with a filtering aid, and filtered. Analyses of the filtrate, a black liquid, indicate a phosphorus content of 3%, a sulfur content of 6.2%, a cobalt content of 2%, and a nitrogen content of 1.5%.
Example 1 8 cadmium oxide. To the reaction mixture at 50 C. there is added 47 gnams (0.74 equivalent) more of cadmium oxide. The reaction mixture is heated at 85 C. for 2 hours. To the (reaction mixture at 70 C. there is added 330 grams (1 equivalent) of the commercial aliphatic primary amine described in Example 9. The amine-treated reaction mixture is heated at 85 C. for 1.5 hours, heated to 115C./ 10 mm., mixed with a filtering aid and filtered. Analyses of the filtered product, a yellow-brown liquid, indicate a phosphorus content of 4.1%, a sulfur content of 8%, a cadmium content of 8.8%, and a nitrogen content of 2.2%. Example 19 To 1,050 grams (1.5 equivalents) of a 50% toluene solution of di (isopropylphenyl)phosphinodithioic acid .at 50 C. there is added 61 grams (1.65 equivalents) of calcium hydroxide. The temperature rises to 77 C.
(exotherm). The reaction mixture is heated at 85-90 C. for 2 hours. To the reaction mixture there is added 180 grams (0.26 equivalent) more of a 50% solution of di (i-sopropylphenyl)phosphinodithioic acid. The mixture is held at 85 C. for 1 hour. Water is removed from Example 20 To 757 grams (1 equivalent) of a 50% toluene solution of di (isopropylphenyl)phosphinodithioic acid at 50 C. there is added 87 grams (1.1 equivalents) of chromous oxalate monohydrate. The reaction mixture is heated at 90 C. for 2 hours. To the reaction mixture at 70 C. there is added 330 grams (1 equivalent) of the commercial aliphatic primary amine described in Example 9. The temperature rises to C. (exotherm). The material is held at C. for 1.5 hours and during this time the color of the material changes from violet to green. The product is heated at 125 C./ 10 mm. and then filtered twice. Analysis of the filtered product, a green liquid, indicates a phosphorus content of 2.4%, a sulfur content of 4.4%, a chromium content of 1.29%, and a nitrogen content of 1.0%
As indicated above, the compositions of this invention are useful as additives for lubricating oils. The lubricating oils in which the additives of this invention are useful may be of synthetic, animal, vegetable, or mineral origin. Ordinarily, mineral lubricating oils are preferred by reason of their availability, general excellence, and low cost. For certain applications, oils belonging to one of the other three groups may be preferred. For instance, synthetic polyester oils such as didodecyl adipate and di 2 ethylhexyl sebacate are often preferred as jet engine lubricants. Normally the lubricating oils preferred will be fluid oils ranging in viscosity from about 40 Saybolt Universal seconds at 100 F. to about 200 Saybolt Universal seconds at 210 F.
The concentration of the phosphorusand nitrogencontaining compositions of this invention to be used in a lubricant depends primarily upon the type of oil used and the nature of the service to which the lubrication composition is to be subjected. In most instances the concentration will range from about 0.001% to about 5% by weight of a lubricant.
The lubricating oil compositions of this invention may also contain other additives such as ashless dispersants, metal-containing dispersants, anti-foam agents, colorstabilizers, anti-freeze agents, pour point depressing agents, auxiliary oxidation-inhibiting agents, corrosioninhibiting agent-s, metal-deactivating agents, de-emulsifying agents, extreme pressure improving agents, etc.
When the compositions of this invention are used in combination with phenyl beta-naphthylamjne in a lubricating oil,-an unusual oxidation inhibiting effect is noted.
Detergents useful in conjunction with the phosphorusand nitrogen-containing compositions of this invention in lubricants include normal or basic salts of petroleum naphtheni-c. acids, petroleum sulfonic acids, oil-soluble fatty acids, ashless detergents such as the reaction prodnot of triethylene tetramine with an alkenyl substituted succinic anhydride having at least 50 carbon atoms in the alkenyl substituent, and a copolymer of 5 parts of betadiethyl aminoethyl acrylate with parts of dodecyl methacrylate, etc. Others include barium mahogany sulfo'nate, the barium salt of the phosphorus acids obtained by the reaction of'polyisobutene (molecular weight of 1000) with phosphorus pentasulfide, and the calcium salt of didodecyl benzene sulfonate.
Anti-foam agents include polymeric alkyl siloxanes, poly(.a1kyl methaorylates) and a condensation product of alkyl phenol with formaldehyde and an amine. Pour point depressing agents are illustrated by polymers of ethylene, propylene, or isobutene ,and poly(alkyl methacrylates). Corrosionand oxidation-inhibiting agents include 4 methyl 2,6, di tert butylphenol, N,N' sec butyl phenylene diamine, basic metal petroleum sulfates, metal phenates, amines, benzylthiocyanates, etc. Film strength agents include, e.g., chlorinated paraflin oils containing from 20 to 70% of chlorine, chlorinated eicosane wax .containing from 50 to 60% of chlorine, hexachloro-distearic acids, sulfurized sperm oil, sperm oil, corn oil, etc. Viscosity index irnprovers include, e.g., polymerized and copolymerized alkyl methacry-lates, polymerized butene, etc.
To prepare the final oil compositions, the compositions of this invention may simply be added to the oil at the appropriate concentration. Ordinarily, a concentrate of the additive is prepared by dissolving it in a limited amount of the oil, optionally with other additives, and the concentrate is then diluted with additional amounts of the oil to prepare the final oil composition. The following lubricants are set forth for the purpose of illustration. All percentages are by weight.
Example A Percent SAE mineral lubricating oil 98.0 Product of Example 7 2.0 Example B Mineral lubricating oil having a viscosity of 99 SUS (Saybolt Universal seconds) at 100 F. to 39 SUS at 210 F. and viscosity index of 93 89.0 Neutral barium salt of the steam hydrolyzed reaction product of polyisobutene (molecular weight of 48,000) with phosphorus pentasulfide 7.0 Carbonated, basic barium salt of sperm oil acid 1.5 Product of Example 1 2.0 Polymeric alky-l acrylate VI improver and pour point depressant 0.48 Polymeric alkyl siloxane anti-foam agent 0.02
Example C Synthetic polyester lubricating oil (trimethylolpropane ester of a C carboxylic acid) having a viscosity of 115 SUS at 100 F. to 42.4 SUS at 210 Example F Synthetic polyester lubricating oil described in Example C 93.5 Phenyl beta-naphthylamine 3.0 Product of Example 1 3.5
Example G SAE 20 mineral lubricating oil 96.0 Phenyl beta-naphthylamine 0.01 Product of Example 7 3.49
Example H SAE 20 mineral lubricating oil 99.97 Phenyl beta-naphthylamine 0.01 Product of Example 1 0.02
. Example I SAE 20 mineral lubricating oil 99.0 4-methyl-2,6-di-tert-butylphenol 0.999 Product of Example 7 0.001
Example J Mineral oil as described in Example B 95.0 Carbonated, basic barium salt of phosphorus trichlo- 12 ride and chlorinated polyisobutene (100,000 molecular weight) Tetraethylene pentamine acylated with a substituted succinic anhydride having a polyisobutenyl radical Tetraethylene pentamine acylated with a substituted succinic anhydride having a polyisobutenyl radical having (molecular weight of 850) as substituent 2.5
Example L SAE 20 mineral lubricating oil 92 Tetraethylene pentamine acylated with a substituted succinic anhydride having a polyisobutenyl radical (molecular weight of 850) as substituent 3 Product of Example 2 5 The compositions of this invention are useful for improving the wear properties of lubricating oils, when incorporated therein in additive quantities. The wear properties of a lubricant are measured by the Four Ball Wear test. In this test, four /2" diameter SAE 52100 steel balls are arranged in a tetrahedral formation and the top ball is made to rotate against the three bottom balls, the points of contact being lubricated by the test lubricant. The top ball is rotated at 600 rpm, loaded against the three bottom balls with a 40 kilogram weight, for a period of 2 hours. During the test, the lubricating oil and steel balls are maintained at a temperature of 200 F. At the end of the test, the steel balls are examined for wear, evidenced by circular scars at the indicated points of contact. The diameter of these scars is measured and reported as an average. The lubricant of Example B allows an average scar diameter of 0.40 mm., whereas a lubricant identical with Example B except that it does not contain the product of Example 1, allows an average scar diameter of 0.79 mm. This comparison indicates that the compositions of this invention are good anti-wear agents for lubricating oils.
The lubricant composition of Example B is further useful as an automatic transmission fluid; this is illustrated by its performance in the Chevrolet Powerglide Oxidation Test, CRC Designation L39. This test consists of operating a Chevrolet passenger car Powerglide Transmission for 300 hours under the following conditions: transmission sump temperature, 275 F.; governor pressure, 55-70 p.s.i.; main line pressure, 95 p.s.i.; transmission speed, 1750-1800 r.p.m. This test is regarded in the industry as an important means for evaluating lubricating compositions for use in automatic transmissions. The lubricant is evaluated in terms of (1) the weight loss of the cindered bronze thrust washer due to corrosion, (2) the amounts of varnish and sludge formed on the clutch plates (expressed in terms of a numerical rating between 10, representing no varnish or sludge, and 0, representing maximum varnish or sludge) and (3) the amount of the overall varnish and sludge formed in the transmission (expressed as a numerical rating between 50, representing no varnish or sludge, and 0, representing a maximum amount of sludge or varnish). The lubricant composition of Example B passes this test in all respects with a 0.12% weight loss of the cindered bronze thrust washer, a clutch plate varnish rating of 10, a clutch plate sludge rating of 9.7, an overall varnish rating of 50, and an overall sludge rating of 48.
The utility of the compositions of this invention in synthetic lubricating oils (as in Examples C and D) is illustrated by the performance of particular lubricants in a severe oxidation test, a modification of the procedure indicated in MIL-L-6808D. In this test, air is bubbled 13 through a 250-ml. sample of the test oil at 425 F. containing 1" x 1" x 0.032" panels of copper, titanium, silver, aluminum, and steel for 40 hours at a rate of 3.4 cu. ft./hr. The neutralization number of the oil sample is determined before and after the test according to ASTM designation D974-58T using alpha-naphthalbenzein indicator. Oil sample losses (i.e., due to vaporization) are measured at 5-hour intervals and the tested oil is replenished with fresh test oil sample. The percent increase of the viscosity of the test oil sample is also determined at 5-hour intervals and the weight loss of the metal samples determined at the end of the test. The lubricants of Examples C and D when subjected to this test, show the following:
TABLE 1.OXIDATION TEST AT 425 F.
Example N o.
Acid Number (alpha-naphthal-benzein):
Original 3. 4 1.17 v 07 Final 13. 56 1. 54 4. 08 Percent Viscosity Increase:
15 hrs 716. 12. 2 5. 76 20 hrs 6.32 8. 7 25 hrs 6. 17 18. 6 34 hrS 9. 05 52. 5 Wt. Loss of Metal Piece (mg.) Cu 3. 5 9. 05
1 Base line, the synthetic polyester oil described in Example C.
2 97.5% of the polyester oil described in Example 0 plus 2.5% of phenyl beta-naphthylannne.
The results of the oxidation test, tabulated in Table 1, indicate that compositions of this invention are useful oxidation inhibitors for synthetic polyester oils. The results also indicate that the compositions of this invention act synergistically with phenyl beta-naphthylamine as oxidation inhibitors in synthetic polyester oils. The synergism is indicated for lubricant compositions wherein from about 0.001 to about 5% by weight of a composition of this invention and from about 0.001 to about 5% by weight of phenyl beta-naphthylamine are incorporated. Lubricant compositions containing from about 1% to about 5% by weight of a composition of this invention and from about 0.5% to about 3% of phenyl beta-naphthylamine are preferred, since maximum oxidation inhibition is obtained from the combination when these limits are employed.
Although, as previously indicated, the compositions of this invention have utility as additives in lubricating oils, they are also useful for other purposes. For example, small amounts of the composition of this invention may be incorporated in gasolines and fuel oils as stabilizers or into paint films as oxidation inhibitors. Compositions of this invention are also useful as insecticides.
It is not intended that the examples and illustrations above limit the scope of this invention except as indicated in the appended claims.
What is claimed is: 1. An oil soluble nitrogenand phosphorus-containing composition having the general formula R S A J! wherein R is an aryl or halogen-substituted aryl radical, or an alkaryl radical containing from 7 to about 26 carbon atoms; each of A and B is hydrogen or an aliphatic hydrocarbon radical; M is zinc, calcium, copper, nickel, cobalt, chromium, lead or cadmium; x is the valence of M; and y is from about 0.5 to about 6.
2. The composition of claim 1 wherein M is zinc.
3. The composition of claim 1 wherein A is hydrogen and B is an aliphatic radical containing from 1 to about carbon atoms.
4. The composition of claim 1 wherein A is hydrogen and B is an aliphatic radical containing at least about 12 carbon atoms.
5. The composition of claim 2 wherein contains from 1 to about 40 carbon atoms, at least one of A and B is an aliphatic hydrocarbon radical, and y is 1 or 2.
6. The composition of claim 5 wherein R is a chlorophenyl radical; y is 2; A is hydrogen and B is a tertiary alkyl radical containing from 8 to 30 carbon atoms.
7. The composition of claim 5 wherein R is an isopropylphenyl radical; y is 2; A is hydrogen and B is a tertiary alkyl radical containing from 8 to 30 carbon atoms.
References Cited UNITED STATES PATENTS 2,849,398 8/1958 Moody et al. 25232.7 2,858,332 10/1958 Watson et a1. 260l 2,907,713 10/1959 Lemmon et al 25232.7 3,168,497 2/1965 Twitchett 260429.9 X 3,185,728 5/1965 Schallenberg et al. 260501 OTHER REFERENCES Bailar: Chemistry of the Coordination Compounds, Reinhold Publ. Corp., Baltimore, Md., 1956, pp. 122-123.
TOBIAS E. LEVOW, Primary Examiner.
DANIEL E. WYMAN, HELEN M. MCCARTHY,
Examiners.
L. G. XIARHOS, H. M. S. SNEED,
Assistant Examiners.
Claims (1)
1. AN OIL SOLUBLE NITROGEN- AND PHOSPHORUS-CONTAINING COMPOSITON HAVING THE GENERAL FORMULA
Priority Applications (4)
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US280452A US3351647A (en) | 1963-05-14 | 1963-05-14 | Nitrogen, phosphorus and metal containing composition |
GB14497/64A GB1044810A (en) | 1963-05-14 | 1964-04-08 | Organic phosphinodithioate-amine reaction products |
FR974381A FR1396093A (en) | 1963-05-14 | 1964-05-13 | New nitrogen and phosphorus additives for lubricating oils |
US640761A US3396109A (en) | 1963-05-14 | 1967-01-26 | Lubricants containing reaction product of a metal phosphinodithioate with an amine |
Applications Claiming Priority (1)
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US280452A US3351647A (en) | 1963-05-14 | 1963-05-14 | Nitrogen, phosphorus and metal containing composition |
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Cited By (17)
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US3413327A (en) * | 1966-01-27 | 1968-11-26 | Lubrizol Corp | Preparation of crystalline group ii metal salts of lower alkyl phosphorodithioic acid |
US3439011A (en) * | 1965-09-30 | 1969-04-15 | Texaco Inc | Amine-hydrocarbyl acid-orthophosphate-zinc halide complexes |
US3471540A (en) * | 1967-03-22 | 1969-10-07 | Phillips Petroleum Co | Production of metal salts of dihydrocarbyldithiophosphoric acids |
US3544609A (en) * | 1966-11-10 | 1970-12-01 | British Petroleum Co | Zinc complexes |
US3673231A (en) * | 1970-08-13 | 1972-06-27 | Shell Oil Co | Sec-phosphine dithiophosphinic acid salts |
US3678086A (en) * | 1970-03-27 | 1972-07-18 | Fmc Corp | Complexes of heavy metal salts of acid phosphate esters |
US3791804A (en) * | 1969-10-10 | 1974-02-12 | Standard Oil Co | Fuel and lubricating oil additives transition metal complexes |
US4048324A (en) * | 1973-12-28 | 1977-09-13 | Armand Kohn | Fungicidal composition and method |
US4218377A (en) * | 1977-11-04 | 1980-08-19 | Ciba-Geigy Corporation | Metal salt/amine complexes |
US4377527A (en) * | 1981-03-09 | 1983-03-22 | Standard Oil Company (Indiana) | Ammonia catalyzed preparation of zinc dihydrocarbyl dithiophosphates |
US4618450A (en) * | 1984-11-07 | 1986-10-21 | The Lubrizol Corporation | Aqueous systems containing amino sulfonic acid derivatives of carboxylic acids |
US4867890A (en) * | 1979-08-13 | 1989-09-19 | Terence Colclough | Lubricating oil compositions containing ashless dispersant, zinc dihydrocarbyldithiophosphate, metal detergent and a copper compound |
US5013467A (en) * | 1987-09-16 | 1991-05-07 | Exxon Chemical Patents Inc. | Novel oleaginous composition additives for improved rust inhibition |
US5021173A (en) * | 1988-02-26 | 1991-06-04 | Exxon Chemical Patents, Inc. | Friction modified oleaginous concentrates of improved stability |
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US5262072A (en) * | 1990-06-28 | 1993-11-16 | Ciba-Geigy Corporation | Lubricant composition |
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US2858332A (en) * | 1956-08-17 | 1958-10-28 | Shell Dev | Amine salts of monohaloalkylphosphonic acids |
US2907713A (en) * | 1955-09-08 | 1959-10-06 | Standard Oil Co | Lubricating oil composition |
US3168497A (en) * | 1961-03-06 | 1965-02-02 | Ici Ltd | Catalyst for polyurethane production using a tertiary amine and a zinc salt of a thio acid of phosphorus |
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US2858332A (en) * | 1956-08-17 | 1958-10-28 | Shell Dev | Amine salts of monohaloalkylphosphonic acids |
US3185728A (en) * | 1960-06-20 | 1965-05-25 | Texaco Inc | Ethylene diamine salts of thiophosphonic acids |
US3168497A (en) * | 1961-03-06 | 1965-02-02 | Ici Ltd | Catalyst for polyurethane production using a tertiary amine and a zinc salt of a thio acid of phosphorus |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3439011A (en) * | 1965-09-30 | 1969-04-15 | Texaco Inc | Amine-hydrocarbyl acid-orthophosphate-zinc halide complexes |
US3413327A (en) * | 1966-01-27 | 1968-11-26 | Lubrizol Corp | Preparation of crystalline group ii metal salts of lower alkyl phosphorodithioic acid |
US3544609A (en) * | 1966-11-10 | 1970-12-01 | British Petroleum Co | Zinc complexes |
US3471540A (en) * | 1967-03-22 | 1969-10-07 | Phillips Petroleum Co | Production of metal salts of dihydrocarbyldithiophosphoric acids |
US3791804A (en) * | 1969-10-10 | 1974-02-12 | Standard Oil Co | Fuel and lubricating oil additives transition metal complexes |
US3678086A (en) * | 1970-03-27 | 1972-07-18 | Fmc Corp | Complexes of heavy metal salts of acid phosphate esters |
US3673231A (en) * | 1970-08-13 | 1972-06-27 | Shell Oil Co | Sec-phosphine dithiophosphinic acid salts |
US4048324A (en) * | 1973-12-28 | 1977-09-13 | Armand Kohn | Fungicidal composition and method |
US4218377A (en) * | 1977-11-04 | 1980-08-19 | Ciba-Geigy Corporation | Metal salt/amine complexes |
US4867890A (en) * | 1979-08-13 | 1989-09-19 | Terence Colclough | Lubricating oil compositions containing ashless dispersant, zinc dihydrocarbyldithiophosphate, metal detergent and a copper compound |
US4377527A (en) * | 1981-03-09 | 1983-03-22 | Standard Oil Company (Indiana) | Ammonia catalyzed preparation of zinc dihydrocarbyl dithiophosphates |
US4618450A (en) * | 1984-11-07 | 1986-10-21 | The Lubrizol Corporation | Aqueous systems containing amino sulfonic acid derivatives of carboxylic acids |
US5013467A (en) * | 1987-09-16 | 1991-05-07 | Exxon Chemical Patents Inc. | Novel oleaginous composition additives for improved rust inhibition |
US5021173A (en) * | 1988-02-26 | 1991-06-04 | Exxon Chemical Patents, Inc. | Friction modified oleaginous concentrates of improved stability |
US5282991A (en) * | 1988-02-26 | 1994-02-01 | Exxon Chemical Patents Inc. | Friction modified oleaginous concentrates of improved stability |
US5262072A (en) * | 1990-06-28 | 1993-11-16 | Ciba-Geigy Corporation | Lubricant composition |
EP0480875A1 (en) * | 1990-10-08 | 1992-04-15 | Ciba-Geigy Ag | Lubricating composition |
US20060258549A1 (en) * | 2005-05-13 | 2006-11-16 | Habeeb Jacob J | Catalytic antioxidants |
US8030257B2 (en) | 2005-05-13 | 2011-10-04 | Exxonmobil Research And Engineering Company | Catalytic antioxidants |
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