US2862882A - Metal amidophosphonate greases - Google Patents
Metal amidophosphonate greases Download PDFInfo
- Publication number
- US2862882A US2862882A US602423A US60242356A US2862882A US 2862882 A US2862882 A US 2862882A US 602423 A US602423 A US 602423A US 60242356 A US60242356 A US 60242356A US 2862882 A US2862882 A US 2862882A
- Authority
- US
- United States
- Prior art keywords
- grease
- metal
- greases
- oil
- lithium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229910052751 metal Inorganic materials 0.000 title claims description 23
- 239000002184 metal Substances 0.000 title claims description 23
- 239000004519 grease Substances 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 25
- 230000001050 lubricating effect Effects 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- -1 alkyl radical Chemical class 0.000 description 25
- 239000003921 oil Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 238000012360 testing method Methods 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 239000002199 base oil Substances 0.000 description 9
- 239000002562 thickening agent Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 7
- 229910052744 lithium Inorganic materials 0.000 description 7
- 230000035515 penetration Effects 0.000 description 7
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 5
- 239000010687 lubricating oil Substances 0.000 description 5
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 5
- 150000003009 phosphonic acids Chemical class 0.000 description 5
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000005461 lubrication Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XXYMGQZRYAIZPS-UHFFFAOYSA-L P([O-])([O-])=O.C(CCCCCCCCCCCCCCCCC)(=O)NC.[Li+].[Li+] Chemical compound P([O-])([O-])=O.C(CCCCCCCCCCCCCCCCC)(=O)NC.[Li+].[Li+] XXYMGQZRYAIZPS-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 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 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- 159000000009 barium salts Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- JHOKTNSTUVKGJC-UHFFFAOYSA-N n-(hydroxymethyl)octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCO JHOKTNSTUVKGJC-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229940037312 stearamide Drugs 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- YEKYKKZCTVBGGM-UHFFFAOYSA-N 2-(hydroxymethyl)octanamide Chemical compound C(O)C(C(=O)N)CCCCCC YEKYKKZCTVBGGM-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- ZTCPEEQYHNDHGB-UHFFFAOYSA-N 6-(6-methylheptoxy)-6-oxohexanoic acid Chemical compound CC(C)CCCCCOC(=O)CCCCC(O)=O ZTCPEEQYHNDHGB-UHFFFAOYSA-N 0.000 description 1
- 229910000906 Bronze Inorganic materials 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000010974 bronze Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002193 fatty amides Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- HSEMFIZWXHQJAE-UHFFFAOYSA-N hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(N)=O HSEMFIZWXHQJAE-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 229940042472 mineral oil Drugs 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- FATBGEAMYMYZAF-UHFFFAOYSA-N octadec-9-enamide Chemical compound CCCCCCCCC=CCCCCCCCC(N)=O FATBGEAMYMYZAF-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229920001515 polyalkylene glycol Chemical class 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 230000013707 sensory perception of sound Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- JZALLXAUNPOCEU-UHFFFAOYSA-N tetradecylbenzene Chemical compound CCCCCCCCCCCCCCC1=CC=CC=C1 JZALLXAUNPOCEU-UHFFFAOYSA-N 0.000 description 1
- MQHSFMJHURNQIE-UHFFFAOYSA-N tetrakis(2-ethylhexyl) silicate Chemical compound CCCCC(CC)CO[Si](OCC(CC)CCCC)(OCC(CC)CCCC)OCC(CC)CCCC MQHSFMJHURNQIE-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- PQRRMYYPKMKSNF-UHFFFAOYSA-N tris(4-methylpentan-2-yl) tris(4-methylpentan-2-yloxy)silyl silicate Chemical compound CC(C)CC(C)O[Si](OC(C)CC(C)C)(OC(C)CC(C)C)O[Si](OC(C)CC(C)C)(OC(C)CC(C)C)OC(C)CC(C)C PQRRMYYPKMKSNF-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M5/00—Solid or semi-solid compositions containing as the essential lubricating ingredient mineral lubricating oils or fatty oils and their use
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/06—Well-defined aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/024—Propene
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/026—Butene
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
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- C10M2229/04—Siloxanes with specific structure
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- C10M2229/046—Siloxanes with specific structure containing silicon-oxygen-carbon bonds
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- C10M2229/048—Siloxanes with specific structure containing carboxyl groups
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- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
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- C10N2010/02—Groups 1 or 11
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- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
Definitions
- This invention relates to grease compositions. More particularly it relates to grease compositions of the multipurpose type having properties of high temperature serviceability, high water resistance and high work stability. In the preferred embodiment of the invention the greases are also characterized by good Wear characteristics.
- a multipurpose grease having a high temperature stability, high Water resistance and high work stability is desirable. Even in ordinary automobile chassis lubrication, a multipurpose grease is useful if it can be used to lubricate different parts of the chassis, thereby avoiding the necessity of, stocking different types of grease and of taking the precautions and the time required to lubricate each fitting with a particular, specified type of grease. It will be apparent that if a multipurpose grease is available which is capable of lubricating all or most of the parts of an automobile chassis, such a grease would provide advantages of convenience and economy.
- Yet another object of the invention is to provide greases having high temperature and work stability.
- Yet another object is to provide greases having high temperature and work stability together With high water resistance.
- Yet another object is to provide greases having high temperature and work stability, low wear properties and high resistance to water.
- oils of lubricating viscosity are thickened .with salts of phosphonic acids of thetype 8 wherein R is an aliphatic radial, preferably an alkyl radical, containing 6 to 24 carbon atoms, and R is hydrogen or a methyl or ethyl radical.
- the preferred grease thickeners of the invention are compounds in which R contains 10 to 20 carbon atoms; R, is hydrogen (i. e., the group R CH is a methylene group); and both of the replaceable hydrogens of the phosphonic acid radical are replaced by a metal suitable for forming greases.
- the metal may be metals of Groups I and II of Mendeleefis Periodic Table and aluminum and lead. Particular metals include the alkali metals such as lithium, sodium and potassium; the alkaline earth metals such as calcium, strontium and barium; the metals cadium and magnesium; and the above-mentioned metals aluminum and lead. Preferred metals are lithium, sodium, calcium, barium and aluminum, and themost advantageous metal is lithium.
- the preferred thickeners are, therefore, alkylamidophosphonates of the preferred metals.
- amidomethane phosphonates suitable for use as grease thickeners in accordance with the invention are the di-sodium, di-lithium, calcium and barium salts of caprylamidomethane phosphonic acid
- Lubricating oils which are useful in the preparation of grease compositions of this invention include a wide variety of lubricating oils, such as naphthenic base, paraffinic base, and mixed base petroleum lubricating oils; other hydrocarbon lubricants, e. g., lubricating oils de- 3 rived from coal products, and synthetic oils, e. g., alkylene polymers (such as polymers of propylene, butylene, etc., and mixtures thereof).
- alkylene oxide-type polymers dicarboxylic acid esters, liquid esters of acids of phosphorus, alkylbenzene polymers, polymers of silicon, etc.
- Synthetic oils of the alkylene oxide-type polymers may be used, c. g., propylene oxide polymers produced by polymerizing propylene oxide in the presence of water or alcohols, e. g., ethyl alcohol; esters of ethylene oxidetype polymers, 6. g., acetylated propylene oxide polymers prepared by acetylating propylene oxide polymers contaiuing hydroxyl groups; polyethers prepared from alkylene glycols, e. g., ethylene glycol, etc.
- the polymeric products prepared from the various alkylene oxides and alkylene glycols may be polyoxyalkylene diols or polyalkylene glycol derivatives; that is, the terminal hydroxy group can remain as such, or one or both of the terminal hydroxy groups can be removed during the polymerization reaction by esterification or etherification.
- Synthetic oils of the dicarboxylic acid ester type include those which are prepared by esterifyiug such dicarboxylic acids as adipic acid, azelaic acid, suberic acid, sebacic acid, alkenyl succinic acid, fumaric aid, maleic acid, etc., with alcohols such as butyl alcohol, hexyl alcohol, Z-ethylhexyl alcohol, dodecyl alcohol, etc.
- Synthetic oils of the alkylbenzene type include those which are prepared by alkylating benzene (e. g., dodecylbenzene, tetradecylbenzene, etc.).
- Synthetic oils of the type of polymers of silicon include the liquid esters of silicon and the polysiloxanes;
- the liquid esters of silicon and the polysiloxanes include those exemplified by tetra(2 ethylhexyl) silicate, tetra(1,3-dimethylbutyl) silicate, tetra(4-methyl-2-pentyl) silicate, tetra(4-methyl-2-pentoxy) disiloxane, hexa( 4- methyl 2 pentoxy)disiloxane, poly (methylsiloxane) poly(methylphenyl) siloxane, and poly-(siloxyglycols),
- the above base oils may be used individually as. such, or in various combinations, wherevermis'cibleor'.wherever made so by the use of mutual'solvent s. i
- the phosphonate compounds of the invention are em; ployed in quantity sufiicient to'thifck en the oil' ad eq uately.
- hard greases maybe produced by appropriateseleg tion of the base oil, the specific thickener and the quantity. of thickener. Proportions of'thick ener as low as 7%,; and as high as 50%' may be employed, but usually about 15 to 30% will be employed.
- the steararnidomethanephosphonic acid is a white crystalline material which sinters at 226 F., and which is soluble in hot water, acetone, ethanol and toluene.
- the lithium salt was readily obtained .by. treating the crude dichlorophosphonate (product of Equation 3 with warm aqueous lithium hydroxide solution and then wash ing the resulting lithium salt,
- salts e. g., the disodium and barium salts, may be prepared by similar techniques.
- This phosphonic acid was prepared by the same process set forth hereinabove, using 325 grams of phosphorus trichloride, 250 grams of methylollauramide, 45 grams of acetic acid, and 250 ml. of chloroform.
- Example 4.Preparati0n of caprylamidomethane phosphonic acid This phosphonic acid was prepared by the process set forth hereinabove, using 200 grams of methylolcaprylamide, 348 grams of phosphorus trichloride, 50 grams of acetic acid, and250 ml. of chloroform. The product p was obtained in 70% yield.
- Salts of the alkylamidomethane phosphonic acids can be readily prepared by conventional methods, e. g., from the acids themselves or from the dichloride intermediates.
- grease compositions thickened with metal salts of alkylamidomethane phosphonic acids were prepared as follows: The alkylamidomethane phosphonic acid was dissolved in the base oil at temperatures of approximately 250 F., after which themixture was cooled to 200 F. An aqueous solution of the metal base (e. g., a metal hydroxide, such as lithium hydroxide) was added, and the whole mixture was heated to 350". F. until substantially dehydrated; then pan cooled. The resulting grease was milled in a laboratory jet mill at 4000 p. s. i. The wellknown Manton-Gaulin mill was used for the larger samples.
- a metal hydroxide such as lithium hydroxide
- Example 5 Preparati0n of grease thickened with lithium stearamidomethane phosphonate 35 pounds of a grease were obtained by heating to 500 F. for 10 minutes a slurry consisting of 23% of lithium stearamidomethane phosphonate and 77% of a California naphthenic base oil having a viscosity of 1685 SSU at 100 F. The product was then pan cooled and milled through a Manton-Gaulin homogenizer at 4000 p. s. i. The resulting grease'had an ASTM dropping point of 500 R, an unworked penetration of 243, and worked penetrations of 303 (after 60 strokes in the ASTM worker packing the grease into two No.
- the data set forth in Table I hereinbelow further illustrate the characteristics of grease compositions thickened with metal alkylamidomethane phosphonates.
- the alkyl radicals described in Table I are the alkyl radicals of the fatty acids used in the preparation of the alkylamidomethane phosphonates.
- the base oil used in each instance was a California 'naphthenic base oil having a viscosity of 450 SSU at strokes (e. g., P i. e., 60 strokes at 77 B), after which the penetration value is obtained.
- the boiling water test was run by placing a S-gram sample of grease in boiling water and noting the time at which the grease began to disintegrate. A grease remaining intact for a period in excess of 60 minutes is considered to have excellent resistance to emulsification in water.
- the Shell roll test is run by placing 75 grams of grease in a Shell roll test apparatus which is described in Military Specification Test Mil-G-10924. However, whereas the Mil-G-10924 test specifies 10 R. P. M. for the apparatus, the data herein were obtained with the apparatus operating at 180 R. P. M. Any grease remaining as a grease for a period of at least 4 hours is considered to have an excellent work stability.
- the loaded wheel bearing test data were obtained by Table II hereinbelow sets forth data obtained with grease compositions prepared from various synthetic base oils using lithium stearamidomethane phosphonate as the thickening agent.
- the silicate" base oil of Test No. 4 was a mixture of hexyl and octyl silicates.
- Thickchar 1 Poly (methylphenyl) Siloxane. 25 263 294 500+ 2. Di (Z-ethylhexyl) Sebacate 25 294 338 500+ 3. Isooctyl Adipate 25 303 342 500+ 4. Silicate 25 266 330 500+ 5. Polypropylene-glycol Diethen 30 227 284 500+
- the grease compositions may contain rust inhibitors, oxidation inhibitors, oiliness agents, antibleeding agents, corrosion inhibitors, extreme pressure agents, etc.
- a grease composition comprising a major proportion of an oil of lubricating viscosity and, in an amount sufficient to thicken said oil to the consistency of a grease, a metal salt of an arnidophosphonate of the formula R;CONHOH2P(OH)2 wherein R is an aliphatic radical containing from 6 to 24 carbon atoms, wherein said metal is a metal selected from the group consisting of alkali metals and alkaline earth metals.
- a grease composition comprising a major proportion of an oil of lubricating viscosity and, in an amount suflicicnt to thicken said oil to the consistency of a grease, a metal salt of an amidophosphonate of the formula nlooNrronn wnn from the group consisting of alkali metals and alkaline earth metals.
- a grease composition comprising a major proportion of a petroleum lubricating oil and, in an amount sufficient to thicken said oiljto the consistency ofia grease, lithium stearamidor'phosphonate 5.
- a grease composition comprising an oil of lubricating viscosity and from 15 to by weight of lithium myristamidomethanephosphonate.
- a grease composition comprising an oil of lubricating viscosity and from 15 to 30% by weight of lithium lauramidomethanephosphonate.
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Description
United States atent Cffice 2,862,882 Patented Dec. 2, 1958 METAL AMIDOPHOSPHON ATE GREASES Bruce W. Hotteu, Orinda, and Frederick 0. Johnson,
Berkeley, Calif., assignors to California Research Corporation, San Francisco, Calif., a corporation of Delaware No Drawing. Application August 6, 1956 Serial No. 602,423
10 Claims. (Cl. 25232.5)
This invention relates to grease compositions. More particularly it relates to grease compositions of the multipurpose type having properties of high temperature serviceability, high water resistance and high work stability. In the preferred embodiment of the invention the greases are also characterized by good Wear characteristics.
In the lubrication of moving parts by greases, i. e., by oils thickened with a suitable thickening agent, several desiderata are present, some of which are more important in one type of service than others. Thus, in one type of service high temperatures may not be encountered, hence a high dropping point (ASTM method) is not important, but resistance to breakdown of the grease structure by water may be important. In other applications resistance to breakdown of the grease structure at high temperatures may be important; therefore, the grease should have a high dropping point although water resistance or some other property may be of secondary importance.
In some types of service, however, where greases are subjected to high temperatures, to contact with water and to high speed mechanical usage tending to break down the grease structure, a multipurpose grease having a high temperature stability, high Water resistance and high work stability is desirable. Even in ordinary automobile chassis lubrication, a multipurpose grease is useful if it can be used to lubricate different parts of the chassis, thereby avoiding the necessity of, stocking different types of grease and of taking the precautions and the time required to lubricate each fitting with a particular, specified type of grease. It will be apparent that if a multipurpose grease is available which is capable of lubricating all or most of the parts of an automobile chassis, such a grease would provide advantages of convenience and economy.
It is an object of the present invention to provide improved grease compositions.
It is a particular object of theinvention to provide grease compositions of the multipurpose type which are capable of effective lubrication under a variety of conditions and are characterized by high resistance to breakdown through contact with water, and to breakdown from high temperature and are characterized by high work stability.
Yet another object of the invention is to provide greases having high temperature and work stability. a
Yet another object is to provide greases having high temperature and work stability together With high water resistance. 1
Yet another object is to provide greases having high temperature and work stability, low wear properties and high resistance to water. i
These and other objects of the invention will be apparent from the ensuing description and the appended claims.
In accordance with the invention oils of lubricating viscosity are thickened .with salts of phosphonic acids of thetype 8 wherein R is an aliphatic radial, preferably an alkyl radical, containing 6 to 24 carbon atoms, and R is hydrogen or a methyl or ethyl radical.
The preferred grease thickeners of the invention are compounds in which R contains 10 to 20 carbon atoms; R, is hydrogen (i. e., the group R CH is a methylene group); and both of the replaceable hydrogens of the phosphonic acid radical are replaced by a metal suitable for forming greases. The metal may be metals of Groups I and II of Mendeleefis Periodic Table and aluminum and lead. Particular metals include the alkali metals such as lithium, sodium and potassium; the alkaline earth metals such as calcium, strontium and barium; the metals cadium and magnesium; and the above-mentioned metals aluminum and lead. Preferred metals are lithium, sodium, calcium, barium and aluminum, and themost advantageous metal is lithium.
The preferred thickeners are, therefore, alkylamidophosphonates of the preferred metals.
Examples of amidomethane phosphonates suitable for use as grease thickeners in accordance with the invention are the di-sodium, di-lithium, calcium and barium salts of caprylamidomethane phosphonic acid Lubricating oils which are useful in the preparation of grease compositions of this invention include a wide variety of lubricating oils, such as naphthenic base, paraffinic base, and mixed base petroleum lubricating oils; other hydrocarbon lubricants, e. g., lubricating oils de- 3 rived from coal products, and synthetic oils, e. g., alkylene polymers (such as polymers of propylene, butylene, etc., and mixtures thereof). Also, alkylene oxide-type polymers, dicarboxylic acid esters, liquid esters of acids of phosphorus, alkylbenzene polymers, polymers of silicon, etc. Synthetic oils of the alkylene oxide-type polymers may be used, c. g., propylene oxide polymers produced by polymerizing propylene oxide in the presence of water or alcohols, e. g., ethyl alcohol; esters of ethylene oxidetype polymers, 6. g., acetylated propylene oxide polymers prepared by acetylating propylene oxide polymers contaiuing hydroxyl groups; polyethers prepared from alkylene glycols, e. g., ethylene glycol, etc.
The polymeric products prepared from the various alkylene oxides and alkylene glycols may be polyoxyalkylene diols or polyalkylene glycol derivatives; that is, the terminal hydroxy group can remain as such, or one or both of the terminal hydroxy groups can be removed during the polymerization reaction by esterification or etherification.
Synthetic oils of the dicarboxylic acid ester type include those which are prepared by esterifyiug such dicarboxylic acids as adipic acid, azelaic acid, suberic acid, sebacic acid, alkenyl succinic acid, fumaric aid, maleic acid, etc., with alcohols such as butyl alcohol, hexyl alcohol, Z-ethylhexyl alcohol, dodecyl alcohol, etc.
Synthetic oils of the alkylbenzene type include those which are prepared by alkylating benzene (e. g., dodecylbenzene, tetradecylbenzene, etc.).
Synthetic oils of the type of polymers of silicon include the liquid esters of silicon and the polysiloxanes; The liquid esters of silicon and the polysiloxanes include those exemplified by tetra(2 ethylhexyl) silicate, tetra(1,3-dimethylbutyl) silicate, tetra(4-methyl-2-pentyl) silicate, tetra(4-methyl-2-pentoxy) disiloxane, hexa( 4- methyl 2 pentoxy)disiloxane, poly (methylsiloxane) poly(methylphenyl) siloxane, and poly-(siloxyglycols),
The above base oils may be used individually as. such, or in various combinations, wherevermis'cibleor'.wherever made so by the use of mutual'solvent s. i
The phosphonate compounds of the invention are em; ployed in quantity sufiicient to'thifck en the oil' ad eq uately. Thus, hard greases maybe produced by appropriateseleg tion of the base oil, the specific thickener and the quantity. of thickener. Proportions of'thick ener as low as 7%,; and as high as 50%' may be employed, but usually about 15 to 30% will be employed.
The following specific examples will serve further to illustrate the practice and advantages of the invention:
PREPARATION OF ALKYLAMIDOMETHANE PHOSPHONATES Examplev l.-Stearamidmethane phosphonate 305 grams (10.1 moles) of par aforma ldehyde were added quickly to 2400 grams (8.67 moles) of liquid Armid HI. The latter is the trademark of a product of Armour Company, Chicago, Illinois. It is a mixture of fatty amides obtained from hydrogenated tallow and consists of 22% hexadecanoylamide (C H -CO'NH 75% stearamide or octadecanoylamide and 3% 9-octadecenoylamide. Because of the predominance of stearamide this mixture is referred to hereinafter as steara'mide'and the reaction products as stearamido products. The reaction mixture .was heated to 230 F. in a four liter stainless steel beaker. The mixture was then heated at 265 F. for five minutes, cooled to 230 F. during ten minutes and pan cooled. The yieldof N methylol-stearamide was almost quantitative The reaction was substantially as follows:
1000 grams (2.6 moles) of the above N-methylolstearamide were added over. a period of four hours to 1300 ml. of chloroform and 865 grams (6.3 moles) of phosphorus trichloride. The mixture was stirred to facilitate dissolution of the methylolamide. 100 ml. (1.75 moles) of glacial acetic acid were added and the stoppered mixture was allowed to stand three days at room temperature. The initial reaction is given by Equation 2 and during the standing period a rearrangement took place in accordance with Equation 3:
7 017E250 QNHCHaOH P 013 CuHasC QNHCH O-QP CnHasC ONHCHr-O-P C 7H 5C O-NH-CHz B Cl 0 C1 The reaction mixture, clear at first, clouded on standing, thickened and formed a. two phase liquid-solid mixture. Most of the chloroform and excess PCl wereremoved by heating to dryness on a hot water bath. The amide product was purified by stirring with 3 liters of water at 160-170 F. for one hour, then cooling to room. temperature; adding a six-fold volume of methanol, suction filtering and washing with a 6:1 methanol-water mixture until free of chloride. The chlorine atoms of the product of Equation 3 are replaced by hydrolysis to yield the phosphonic acid, C H CQ-NH-CH PQ(OH) .Q
The resulting product, which was obtained in a 70% yield, analyzed as follows:
Calculated Found The steararnidomethanephosphonic acid is a white crystalline material which sinters at 226 F., and which is soluble in hot water, acetone, ethanol and toluene.
The lithium salt was readily obtained .by. treating the crude dichlorophosphonate (product of Equation 3 with warm aqueous lithium hydroxide solution and then wash ing the resulting lithium salt,
with water until it was neutral and free of chloride. Other salts, e. g., the disodium and barium salts, may be prepared by similar techniques.
Example 2.Preparati0n of.myristamidomethane phosphonic acid Example 3.- Preparati0n, 0 lauramidomethane phosphonic acid This phosphonic acid Was prepared by the same process set forth hereinabove, using 325 grams of phosphorus trichloride, 250 grams of methylollauramide, 45 grams of acetic acid, and 250 ml. of chloroform. The reaction pro'ducLcontained 9.6% phosphorus (theory=l0.6%); and the saponification number was 385 (theory=385).
Example 4.Preparati0n of caprylamidomethane phosphonic acid This phosphonic acid was prepared by the process set forth hereinabove, using 200 grams of methylolcaprylamide, 348 grams of phosphorus trichloride, 50 grams of acetic acid, and250 ml. of chloroform. The product p was obtained in 70% yield.
Salts of the alkylamidomethane phosphonic acids can be readily prepared by conventional methods, e. g., from the acids themselves or from the dichloride intermediates.
As described and exemplified in further detail below, grease compositions thickened with metal salts of alkylamidomethane phosphonic acids were prepared as follows: The alkylamidomethane phosphonic acid was dissolved in the base oil at temperatures of approximately 250 F., after which themixture was cooled to 200 F. An aqueous solution of the metal base (e. g., a metal hydroxide, such as lithium hydroxide) was added, and the whole mixture was heated to 350". F. until substantially dehydrated; then pan cooled. The resulting grease was milled in a laboratory jet mill at 4000 p. s. i. The wellknown Manton-Gaulin mill was used for the larger samples.
Example 5.Preparati0n of grease thickened with lithium stearamidomethane phosphonate 35 pounds of a grease were obtained by heating to 500 F. for 10 minutes a slurry consisting of 23% of lithium stearamidomethane phosphonate and 77% of a California naphthenic base oil having a viscosity of 1685 SSU at 100 F. The product was then pan cooled and milled through a Manton-Gaulin homogenizer at 4000 p. s. i. The resulting grease'had an ASTM dropping point of 500 R, an unworked penetration of 243, and worked penetrations of 303 (after 60 strokes in the ASTM worker packing the grease into two No.
loaded axially at 550 pounds. The bearings were rotated at a speed of 1750 R. P. M. for 18 hours at 250 F.
a After 1,000 hours izithe Shell Roll Test apparatus the Poo was 353. r
b The weight loss was only 1.6 mg. in the Almen steel-on-bronze wear test; and 0.1 mg. in the Falex 500 pound steel-on-steel wear test. This grease passed pounds in the Timken steel-on-steel test. v 7
at 77 F.) and 347 (after 100,000 strokes in the worker). After using this grease during a 9000-mile test run, the front wheel bearings of a city bus were in good condition.
The data set forth in Table I hereinbelow further illustrate the characteristics of grease compositions thickened with metal alkylamidomethane phosphonates. The alkyl radicals described in Table I are the alkyl radicals of the fatty acids used in the preparation of the alkylamidomethane phosphonates.
The base oil used in each instance was a California 'naphthenic base oil having a viscosity of 450 SSU at strokes (e. g., P i. e., 60 strokes at 77 B), after which the penetration value is obtained.
For the work stability test data, ASTM penetrations (after 60 strokes in the ASTM worker at 77 F.) were obtained on the grease to be tested. The grease was then packed into a No. 206 shielded ball bearing. The packed bearing was rotated at 3450 R. P. M. for 30 minutes at room temperature. The ASTM unworked penetration value of the grease at 77 F. was obtained. The AP data of Table I represent the changes in the ASTM worked penetration values obtained before the grease was packed into the bearing, and the ASTM unworked penetration values obtained after the bearing had been rotated.
The boiling water test was run by placing a S-gram sample of grease in boiling water and noting the time at which the grease began to disintegrate. A grease remaining intact for a period in excess of 60 minutes is considered to have excellent resistance to emulsification in water.
The Timken test and the Almen test are described in Lubricants and Lubrication, by CloWer, published by McGraW-Hill Book Company, 1939, pages 145-148. The Falex tests are described in the Journal of the Institute of Petroleum, vol. 32, April 1946.
The Shell roll test is run by placing 75 grams of grease in a Shell roll test apparatus which is described in Military Specification Test Mil-G-10924. However, whereas the Mil-G-10924 test specifies 10 R. P. M. for the apparatus, the data herein were obtained with the apparatus operating at 180 R. P. M. Any grease remaining as a grease for a period of at least 4 hours is considered to have an excellent work stability.
The loaded wheel bearing test data were obtained by Table II hereinbelow sets forth data obtained with grease compositions prepared from various synthetic base oils using lithium stearamidomethane phosphonate as the thickening agent. The silicate" base oil of Test No. 4 was a mixture of hexyl and octyl silicates.
TABLE II Percent, Dropping Base Oil by wt. P0 P00 Point,
Thickchar 1. Poly (methylphenyl) Siloxane. 25 263 294 500+ 2. Di (Z-ethylhexyl) Sebacate 25 294 338 500+ 3. Isooctyl Adipate 25 303 342 500+ 4. Silicate 25 266 330 500+ 5. Polypropylene-glycol Diethen 30 227 284 500+ In addition to the components noted hereinabove, the grease compositions may contain rust inhibitors, oxidation inhibitors, oiliness agents, antibleeding agents, corrosion inhibitors, extreme pressure agents, etc.
It will, therefore, be apparent that greases have been provided in which the major component is an oil of lubricating viscosity; such oil being thickened with a novel type of thickener; and that the greases have very advantageous properties such as resistance to breakdown due to mechanical action, resistance to water and high dropping points.
We claim:
1. A grease composition comprising a major proportion of an oil of lubricating viscosity and, in an amount sufficient to thicken said oil to the consistency of a grease, a metal salt of an arnidophosphonate of the formula R;CONHOH2P(OH)2 wherein R is an aliphatic radical containing from 6 to 24 carbon atoms, wherein said metal is a metal selected from the group consisting of alkali metals and alkaline earth metals.
2. A grease composition comprising a major proportion of an oil of lubricating viscosity and, in an amount suflicicnt to thicken said oil to the consistency of a grease, a metal salt of an amidophosphonate of the formula nlooNrronn wnn from the group consisting of alkali metals and alkaline earth metals.
20s. ball bearings, such that the bearings were full of thetestgrease. The-ball hearings were mounted on a splined shaft and spring.
3. A grease composition comprising a major proportion of a petroleum lubricating oi1 and, inan amount suflicient to thicken said oil to the consistency ofa grease; ametal amidopho'sphoinate of the formula l OLi t r RICONHCHIP E OLi wherein R is an alkyl radical containing= from to 20 carbon atoms. p
4. A grease composition comprising a major proportion of a petroleum lubricating oil and, in an amount sufficient to thicken said oiljto the consistency ofia grease, lithium stearamidor'phosphonate 5. Av-grease compositiomcomprising a petroleum mineraloil and from 7% to 50% byweight of a metal salt of an amidophosphonate ofthe formula moonnorn 'wnp eral oil and from to 30% by weight ofra metal salt of an amidophosphonateof the formula R1CONHCH21(OH)2 wherein R is analiphatic-radical containing from 6 to 24 carbon atoms, wherein said metal is a metal selected from the'group consisting of alkali metals, and alkaline ing viscosity and from 15 to 30% by weight of lithium wherein R is an aliphatic radicalcontaining from 6 to a ;caprylamidomethanephosphonate.
9. A grease composition comprising an oil of lubricating viscosity and from 15 to by weight of lithium myristamidomethanephosphonate.
' 10. A grease composition comprising an oil of lubricating viscosity and from 15 to 30% by weight of lithium lauramidomethanephosphonate.
References Cited in the file of this patent UNITED STATES PATENTS 2,304,156 Engelmann et a1. Dec. 3, 1942
Claims (1)
1. A GREASE COMPOSITION COMPRISING A MAJOR PROPORTION OF AN OIL OF LUBRICATING VISCOSITY AND, IN AN AMOUNT SUFFICIENT TO THICKEN SAID OL TO THE CONSISTENCE OF A GREASE A METAL SALT OF AN AMIDOPHOSPHONATE OF THE FORMULA
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US602423A US2862882A (en) | 1956-08-06 | 1956-08-06 | Metal amidophosphonate greases |
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US602423A US2862882A (en) | 1956-08-06 | 1956-08-06 | Metal amidophosphonate greases |
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US602423A Expired - Lifetime US2862882A (en) | 1956-08-06 | 1956-08-06 | Metal amidophosphonate greases |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0201006A2 (en) * | 1985-05-04 | 1986-11-12 | Hoechst Aktiengesellschaft | 1-Acylamido-alkyl-phosphonic acids and their salts, process for their preparation and their use as surfactants |
EP0385014A1 (en) * | 1987-11-20 | 1990-09-05 | CROMPTON & KNOWLES CORPORATION | Process for preparation of substituted aminomethylphosphonic acids |
US5925601A (en) * | 1998-10-13 | 1999-07-20 | Ecolab Inc. | Fatty amide ethoxylate phosphate ester conveyor lubricant |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2304156A (en) * | 1940-03-07 | 1942-12-08 | Du Pont | Organic compound and process of preparing the same |
-
1956
- 1956-08-06 US US602423A patent/US2862882A/en not_active Expired - Lifetime
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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US2304156A (en) * | 1940-03-07 | 1942-12-08 | Du Pont | Organic compound and process of preparing the same |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0201006A2 (en) * | 1985-05-04 | 1986-11-12 | Hoechst Aktiengesellschaft | 1-Acylamido-alkyl-phosphonic acids and their salts, process for their preparation and their use as surfactants |
EP0201006A3 (en) * | 1985-05-04 | 1987-07-22 | Hoechst Aktiengesellschaft | 1-acylamido-alkyl-phosphonic acids and their salts, process for their preparation and their use as surfactants |
EP0385014A1 (en) * | 1987-11-20 | 1990-09-05 | CROMPTON & KNOWLES CORPORATION | Process for preparation of substituted aminomethylphosphonic acids |
US5925601A (en) * | 1998-10-13 | 1999-07-20 | Ecolab Inc. | Fatty amide ethoxylate phosphate ester conveyor lubricant |
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