US2685567A - Lubricant composition containing alkyl-mercaptoalkyl phosphites - Google Patents
Lubricant composition containing alkyl-mercaptoalkyl phosphites Download PDFInfo
- Publication number
- US2685567A US2685567A US259015A US25901551A US2685567A US 2685567 A US2685567 A US 2685567A US 259015 A US259015 A US 259015A US 25901551 A US25901551 A US 25901551A US 2685567 A US2685567 A US 2685567A
- Authority
- US
- United States
- Prior art keywords
- phosphite
- base
- incorporated
- phosphites
- lubricant
- 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
- 239000000314 lubricant Substances 0.000 title claims description 34
- 239000000203 mixture Substances 0.000 title description 4
- -1 HYDROGEN ATOMS Chemical group 0.000 claims description 44
- 230000003647 oxidation Effects 0.000 claims description 18
- 238000007254 oxidation reaction Methods 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 15
- 230000006866 deterioration Effects 0.000 claims description 12
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 239000003599 detergent Substances 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 229910052711 selenium Inorganic materials 0.000 claims description 4
- 239000011669 selenium Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 101150064205 ESR1 gene Proteins 0.000 claims 1
- 239000002585 base Substances 0.000 description 35
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 17
- 239000000654 additive Substances 0.000 description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 7
- 125000004432 carbon atom Chemical class C* 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000010688 mineral lubricating oil Substances 0.000 description 7
- 239000002480 mineral oil Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- 150000002895 organic esters Chemical class 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 5
- 229910052791 calcium Inorganic materials 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000003209 petroleum derivative Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 239000010685 fatty oil Substances 0.000 description 2
- 229910052745 lead Inorganic materials 0.000 description 2
- 230000001050 lubricating effect Effects 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000012188 paraffin wax Chemical class 0.000 description 2
- 235000019809 paraffin wax Nutrition 0.000 description 2
- 235000019271 petrolatum Nutrition 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical compound [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical class OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
- CFWRDBDJAOHXSH-SECBINFHSA-N 2-azaniumylethyl [(2r)-2,3-diacetyloxypropyl] phosphate Chemical compound CC(=O)OC[C@@H](OC(C)=O)COP(O)(=O)OCCN CFWRDBDJAOHXSH-SECBINFHSA-N 0.000 description 1
- AHZRNZSJQJDAQP-UHFFFAOYSA-N 2-cyanooctadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(C#N)C(O)=O AHZRNZSJQJDAQP-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- KGYYLUNYOCBBME-UHFFFAOYSA-M 4-fluoro-2-phenyl-4-(4-propylcyclohexyl)cyclohexa-1,5-diene-1-carboxylate Chemical compound C1CC(CCC)CCC1C1(F)C=CC(C([O-])=O)=C(C=2C=CC=CC=2)C1 KGYYLUNYOCBBME-UHFFFAOYSA-M 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Chemical class C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 239000004129 EU approved improving agent Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Chemical class O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- BUSBFZWLPXDYIC-UHFFFAOYSA-N arsonic acid Chemical class O[AsH](O)=O BUSBFZWLPXDYIC-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 159000000009 barium salts Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003470 sulfuric acid monoesters Chemical class 0.000 description 1
- 239000003784 tall oil Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Chemical class OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- QOQNJVLFFRMJTQ-UHFFFAOYSA-N trioctyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OCCCCCCCC QOQNJVLFFRMJTQ-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/10—Thio derivatives
- C10M137/105—Thio derivatives not containing metal
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
-
- 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
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- 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
- C10M2205/16—Paraffin waxes; Petrolatum, e.g. slack wax
-
- 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
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/027—Neutral salts thereof
-
- 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
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
- C10M2207/046—Hydroxy ethers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
- C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/129—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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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/141—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings monocarboxylic
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/142—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings polycarboxylic
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/144—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/146—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings having carboxyl groups bound to carbon atoms of six-membeered aromatic rings having a hydrocarbon substituent of thirty or more carbon atoms
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- C10N2060/04—Oxidation, e.g. ozonisation
Definitions
- This invention relates to lubricants having imformed by the removal of hydrogen atoms from proved stability and lubricating properties.
- saturated aliphatic hydrocarbons X is a non- More particularly, this invention pertains to comoygen .chalkogen element, preferably sulfur and pounded lubricants having incorporated therein 1 is an integer of from 1 to 4.
- Additive agents of this invention can be pretemperature anti-oxidant and extreme pressure pared by any suitable means such as the methods properties.
- Any suitable means such as the methods properties.
- Serial Various lubricants whether of natural and/or No. 381,561 filed July 13, 1948 and which has synthetic origin such as petroleum hydrocarbons, matured into U. S. Patent No. 2,587,616 of which fixed fats and oils and fractions thereof as Well this application is a continuation-in-part, are
- One object of this invention is to impart extreme pressure properties to base lubricants and inhibit their oxidation over a wide temperature range. Another object of this invention is to prevent oxidation of base lubricants. Still another object of this invention is to produce an improved lubricant of outstanding stability and Bis 3 cyclohexylmercaptopropyl) phosphite extreme pressure properties by incorporating in Tris 3-c cloheximercaptopropyl) phosphite said base lviloriciant at, pargicular type of additive 3o 3 cyclopgmylmeicapto 2 methy1propy1 phosphite free from o jec iona 1e 0 ors.
- the preferred class of compounds comprises the alkyl-mercaptoalkyl phosphites, which Dthexyl 3octylmercapto'z'propylbutyl phosphite are aliphatic phosphites in which the aliphatic DIOYPIOheXYI 3 cyclohexylmercaptopropyl phos' radicals replacing the hydrogen atoms of the phlte hydroxyl groups of phosphorous acid, are of the -ethylhexyl 3-amyselenylpropyl phosphite general formula in which R and 3 amylmercaptopropyl dithio dicyclohexyl phosare polar or non-polar substituted non-aromatic Dhite hydrocarbyl radicals and preferably represent Chlorobenzyl bis(3-amylmercaptopropyl) phosmono and divalent 01-015 hydrocarbon radicals phite 3 Chloropheny
- non-oxygen chalkogen ether containing phosphites of this invention can be used to improve base lubricants, in concentrations varying from 0.001% to 20% and preferably from 0.1% to 5% by weight.
- Organic bases include various nitrogen bases as primary, secondary, tertiary amines and quaternary ammonium compounds, e. g., benzyl trirnethyl ammonium hydroxide.
- detergent-forming acids are the fatty acids of say, 10 to 30 carbon atoms, tall-oil acids, rosin acids, wool-fat acids, paraffin-wax acids (produced by oxidation of paraifin Wax), chlorinated fatty acids, aromatic hydroxy fatty acids, paraffin-wax benzoic acids, various alkyl salicyclic acids, phthalic acid monoesters, aromatic keto acids, aromatic ether acids, diphenols such as di-(alkylphenol) sulfides and disulfides,
- methylene bis-alkyl phenols such as may be produced by treatment of alkyl aryl hydrocarbons or high-boiling petroleum oils with sulfuric acid; sulfuric acid monoesters; phosphoric, arsonic and antimony acid monoand diesters, including the corresponding thiophosphoric and arsonic acids and the like.
- alkaline earth phosphate di-esters including the thiophosphate (ii-esters; the alkaline earth diphenolates, specifically, the calcium and barium salts of diphenol monoand poly-sulfides.
- Non-metallic detergents include compounds such as the phosphatides (lecithin and cephalin) certain fatty oils such as rapeseed oils, Voltolized fatty or mineral oils and the like.
- An excellent detergent for the present purpose is the calcium salt of oil-solule petroleum sulfonic acids. This may be present advantageously in the amount of about 0.025% to 0.2% sulfate ash. Also, alkaline metal salts of alkyl phenolaldehyde condensation products are excellent detergents.
- Corrosion inhibitors or anti-rusting compounds may also be present, such as dicarboxylic acids of 16 or more carbon atoms; alkali metal and alkaline earth salts of sulfonic acids and fatty acids, organic compounds containing an acidic radical in close proximity to a nitrile, nitro, or nitroso group (e. g., alpha-cyanostearic acid), glycidyl phenyl ether, wax disulfide, etc.
- Additional ingredients may comprise oil-soluble urea or thiourea derivatives, e. g., urethanes, allophanates, carbazides, carbazones, etc., polyisobutylene polymers, unsaturated polymerized esters of fatty acids and monohydric alcohols and other high-molecular-weight oil-soluble compounds.
- oil-soluble urea or thiourea derivatives e. g., urethanes, allophanates, carbazides, carbazones, etc.
- polyisobutylene polymers unsaturated polymerized esters of fatty acids and monohydric alcohols and other high-molecular-weight oil-soluble compounds.
- the amount of additive used may vary from 0.01 to 2% or higher. However, substantial; improvement is obtained by using amounts ranging from 0.1 to 0.5% in combination with the primary additive of this invention.
- An improved lubricant comprising a mineral lubricating oil base having incorporated therein from 0.01 to 5% by weight of tri(3-amylmercaptopropyl) phosphite.
- An improved lubricant comprising a mineral lubricating oil base having incorporated therein from 0.01 to 5% by weight of bis(3-amylmercaptopropyl) phosphite.
- An improved lubricant comprising a mineral lubricating oil base having incorporated therein from 0.01 to 5% by weight of tris(3-cyclohexylmercaptopropyl) phosphite.
- An improved lubricant comprising a mineral lubricating oil base having incorporated therein from 0.01 to 5% by weight of 5-pentadecyl1nercaptopentyl phosphite.
- An improved lubricant comprising a mineral lubricating oil base having incorporated therein from 0.01 to 5% by weight of 3-cyclophenylmercapto-2-methylpropyl phosphite.
- An improved lubricant comprising a mineral oil base having incorporated therein a minor amount sufiicient to stabilize said oil base against oxidation deterioration of tris(3-amylmercapto propyl) phosphite.
- An improved lubricant comprising a mineral oil base having incorporated therein a minor amount sunicient to stabilize said oil base against oxidation deterioration of bis(3-amylmercapto propyl) phosphite.
- An improved lubricant comprising a mineral oil base having incorporated therein a minor amount sufficient to stabilize said oil base against oxidation deterioration of tris(3-cyclohexylmercaptopropyl) phosphite.
- An improved lubricant comprising a mineral oil base having incorporated therein a minor amount sufiicient to stabilize said oil base against oxidation deterioration of 5-pentadecyl mercaptopentyl phosphite.
- An improved lubricant comprising a mineral oil base having incorporated therein a minor amount sufficient to stabilize said oil base against oxidation deterioration of 3-cyclopentylmercapto-2-methylpropyl phosphite.
- An improved lubricant comprising a petroleum hydrocarbon base having incorporated therein in an amount suificient to stabilize said base against oxidation deterioration of an alkylmercaptoalkyl ester of phosphorous acid in which at least two hydrogen atoms of the acid are replaced by alkylmercaptoalkyl radicals.
- An improved lubricant comprising a petroleum hydrocarbon base having incorporated therein in an amount sufiicient tostabilize said base against oxidation deterioration of an organic ester of phosphorous acid in which the organic radicals which replace hydrogen atoms from the hydroxyl groups of the acid have the formula RSR' in which R and R are saturated aliphatic hydrocarbon radicals, R and R containing from 1 to 15 carbon atoms.
- An improved lubricant comprising a mineral oil base having incorporated therein in an amount sufficient to stabilize said base against oxidation deterioration of an organic ester of phosphorous acid in which the organic radicals which replace hydrogen atoms from the hydroxyl groups of the acid have the formula -RSR'- in which R and R are saturated aliphatic hydrocarbon radicals, R and R containing from 1 to 15 carbon atoms.
- An improved lubricant comprising a petroleum hydrocarbon base having incorporated therein in an amount sufficient to stabilize said base against oxidation deterioration of an organic ester of phosphorous acid in which the organic radicals which replace hydrogen atoms from the hydroxyl groups of the acid have the formula RX-R'- in which R and R each are saturated aliphatic hydrocarbon radicals, R and R contain from 1 to 15 carbon atoms, X is an element selected from the group consisting of sulfur and selenium.
- An improved lubricant comprising a liquid hydrocarbon lubricant base having incorporated therein in an amount suificient to stabilize said base against oxidation deterioration of an organic ester of phosphorous acid in which the organic radicals which replace hydrogen atoms from the hydroxyl groups of the acid have the formula RXR'- in which R and R each are saturated nonaromatic hydrocarbon radicals containing from 1 to 15 carbon atoms, X is an element selected from the group consisting of sulfur and selenium.
- An improved lubricant comprising a mineral lubricating oil base, from about 0.01% to about 5%, by weight, of tris(3-amylmercapto propyl) phosphite, and from about 0.01 to about 2% of an oil-soluble calcium petroleum sulfonate.
- An improved lubricant comprising a liquid hydrocarbon lubricant base, having incorporated therein, in an amount suflicient to stabilize said base against oxidation deterioration, an organic ester of phosphorous acid in which the organic radicals which replace hydrogen atoms of the hydroxyl groups of said acid have the formula -RXR' in which R and R each are saturated non-aromatic hydrocarbon radicals containing from 1 to 15 carbon atoms, X is an element selected from the group consisting of sulfur and selenium, and from about 0.01% to about 2% of an oil-soluble detergent.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
Patented Aug. 3, 1954 I UNITED STATES PATENT OFFICE LUBRICANT COMPOSITION CONTAINING ALKYL-MERCAPTOALKYL PHOSPHITES Denham Harman, IOrinda, Califl, assignor to Shell Development Company, Emeryville, Calif., a corporation of Delaware No Drawing. Application November 29, 1951, Serial No. 259,015
17 Claims. (Cl. 252-334) This invention relates to lubricants having imformed by the removal of hydrogen atoms from proved stability and lubricating properties. saturated aliphatic hydrocarbons; X is a non- More particularly, this invention pertains to comoygen .chalkogen element, preferably sulfur and pounded lubricants having incorporated therein 1 is an integer of from 1 to 4.
an additive agent possessing outstanding Wide 5 Additive agents of this invention can be pretemperature anti-oxidant and extreme pressure pared by any suitable means such as the methods properties. employed in the copending application, Serial Various lubricants whether of natural and/or No. 381,561 filed July 13, 1948 and which has synthetic origin such as petroleum hydrocarbons, matured into U. S. Patent No. 2,587,616 of which fixed fats and oils and fractions thereof as Well this application is a continuation-in-part, are
as synthetic lubricants derived from olefinic polyparticularly preferred. mers, organic esters and the like, are generally Illustrative examples of additive agents of this affected by oxygen, air or under various oxidizinvention include:
ing conditions resulting in the formation of undesirable products and deleterious reactions which markedly decrease the useful life of such products or render them useless within a relatively short period of time for their intended purpose such as lubrication of engine parts. Additionally this phenomenon alters both the chemical and physical properties of both the additives and bas lubricant and in the case of the additives possessing extreme pressure properties, such properties are altered rapidly or dissipate, resulting at the best only in a temporary solution to extreme pressure lubrication.
One object of this invention is to impart extreme pressure properties to base lubricants and inhibit their oxidation over a wide temperature range. Another object of this invention is to prevent oxidation of base lubricants. Still another object of this invention is to produce an improved lubricant of outstanding stability and Bis 3 cyclohexylmercaptopropyl) phosphite extreme pressure properties by incorporating in Tris 3-c cloheximercaptopropyl) phosphite said base lviloriciant at, pargicular type of additive 3o 3 cyclopgmylmeicapto 2 methy1propy1 phosphite free from o jec iona 1e 0 ors. Other objects of th 1 r 1) this invention will be apparent from the follow- B158 cyclopentylmercapto 2 me y p opy B-amylmercaptopropyl phosphite Bis(3-amylmercaptopropyl) phosphite Tris(3-amylmercaptopropyl) phosphite 5-10entadecylmercaptopentyl phosphite Bis 5-pentadecylmercaptopentyl) phosphite Tris 5 -pentadecylmercaptopentyl) phosphite 3-amylmercapto-2methylp-ropyl phosphite Bis(3-amylmercapto-2-methylpropyl) phosphite Tris(3-amylmercapto-2-methylpropy1) phosphite 3-octylmercapto2-propylbutyl phosphite Bis(3-octylmercapto-2-propylbutyl) phosphite Tris(3-octylmercapto-2-propylbutyl) phosphite 3 (1,1,3 trimethylbutylmercapto) 2 methylpropyl phosphite BisES (1,1,3 trimethylbutylmercapto) 2- methylpropyl] phosphite Tris[3 (1,1,3 trimethylbutylmercapto) 2- methylpropyl] phosphite 3-cyclohexylmercaptopropyl phosphite ing description of this invention phosphite l l l r 2 h 1 r0 1 It has now been discovered that stable, excelgifg fig Openty me capto met y p py lent extreme pressure lubricants can be prepared by incorporating into a base lubricant minor amounts of a particular type of organo phosphites characterized by the presence of nonoxygen chalkogen atoms solely in the form of 3-amylselenylpropyl phosphite Bis 3-amylselenylpropyl) phosphite Tris(3-amylselenylpropyl) phosphite Trisl3 isobutylmercapto 2,3 dimethylbutyll phosphite non'oxy ether groups m replacmg hydrogen Octyl bis(3-amylmercaptopropyl) phosphite atoms of the hydroxy groups of phosphorous Benzyl bis (S-amylmercaptopropyl) phosphite acids. The preferred class of compounds comprises the alkyl-mercaptoalkyl phosphites, which Dthexyl 3octylmercapto'z'propylbutyl phosphite are aliphatic phosphites in which the aliphatic DIOYPIOheXYI 3 cyclohexylmercaptopropyl phos' radicals replacing the hydrogen atoms of the phlte hydroxyl groups of phosphorous acid, are of the -ethylhexyl 3-amyselenylpropyl phosphite general formula in which R and 3 amylmercaptopropyl dithio dicyclohexyl phosare polar or non-polar substituted non-aromatic Dhite hydrocarbyl radicals and preferably represent Chlorobenzyl bis(3-amylmercaptopropyl) phosmono and divalent 01-015 hydrocarbon radicals phite 3 Chlorophenyl bis(3-amylmercaptopropyl) phosphite Diallyl -pentadecylmercaptopentyl phosphite Dioleyl 3-octylmercapto-2-propyl phosphite Mono 3 octyl merctapto-2-propyl dithio octyl phosphite Tris(3-amyldimercaptopropyl) phosphite Poly phosphites can be used and include such compounds as:
C1CH2CH2OP( OH) OCH2CH2S- CHzCHaOP (OI-I) CHcCI-IzCl CH2=CHCH2OP OH) OCHaCI-Ic SCH2CH2OP (OH) CI-IzCI-I CHz Metal and nitrogen base salts of the acidic phosphorous esters of this invention can also be used as oil improving agents such as the Na, K, Li, Ca, Ba, Al, Zn and Pb as well as the amine salts of any of the above esters or mixtures thereof. Included among the preferred salts are:
Na, Ca and Pb salts of bis(3-arnylmercaptopropyl) phosphite Na, Ca, Zn and Al salts of cyclohexyl mercaptopropyl phosphite Di-Z-ethylhexyla-mine salt of bis(3-amy1mercaptopropyl) phosphite icyclohexylamine salt of cyclohexylmercaptopropyl phosphite Morpholine salt of 3-octylmercaptopropyl phosphite The non-oxygen chalkogen ether containing phosphites of this invention can be used to improve base lubricants, in concentrations varying from 0.001% to 20% and preferably from 0.1% to 5% by weight.
To illustrate the pronounced superiority of additives of this invention as anti-oxidants, the following lubricating compositions were prepared and evaluated by the Dornte Oxidation Stability Test as described in the National Petroleum News, September 1'7, 1941, pages R294-296, and in the High-Temperature Oxidation Apparatus of H. Diamond et al., which is fully described in the general papers presented before the Division of Petroleum Chemistry at the meeting of the American Chemical Society (September 18- 23, 1949, Atlantic City, New Jersey) on pages 31-45 of the reprints. Results of such tests are presented below.
[Baez Refined Mineral Lubricating Oil] Dornte Oxidation High Temperature Test (150 C; 150 Test, 260 0., 250 cc. (1112) cc. (mm) Cu crankcase Cu crankcase Cat. Get. Get. None 5 5 6.5 1.6% tri-octyl phosphite. 13 ll) 32 28 1.84% tris(3-amyl-mercaptopropyl) phcsphita 50 120 36 40 Co, etc. Organic bases include various nitrogen bases as primary, secondary, tertiary amines and quaternary ammonium compounds, e. g., benzyl trirnethyl ammonium hydroxide.
Examples of detergent-forming acids are the fatty acids of say, 10 to 30 carbon atoms, tall-oil acids, rosin acids, wool-fat acids, paraffin-wax acids (produced by oxidation of paraifin Wax), chlorinated fatty acids, aromatic hydroxy fatty acids, paraffin-wax benzoic acids, various alkyl salicyclic acids, phthalic acid monoesters, aromatic keto acids, aromatic ether acids, diphenols such as di-(alkylphenol) sulfides and disulfides,
, methylene bis-alkyl phenols; sulfonic acids such as may be produced by treatment of alkyl aryl hydrocarbons or high-boiling petroleum oils with sulfuric acid; sulfuric acid monoesters; phosphoric, arsonic and antimony acid monoand diesters, including the corresponding thiophosphoric and arsonic acids and the like.
Additional detergents are the alkaline earth phosphate di-esters, including the thiophosphate (ii-esters; the alkaline earth diphenolates, specifically, the calcium and barium salts of diphenol monoand poly-sulfides.
Non-metallic detergents include compounds such as the phosphatides (lecithin and cephalin) certain fatty oils such as rapeseed oils, Voltolized fatty or mineral oils and the like.
An excellent detergent for the present purpose is the calcium salt of oil-solule petroleum sulfonic acids. This may be present advantageously in the amount of about 0.025% to 0.2% sulfate ash. Also, alkaline metal salts of alkyl phenolaldehyde condensation products are excellent detergents.
Corrosion inhibitors or anti-rusting compounds may also be present, such as dicarboxylic acids of 16 or more carbon atoms; alkali metal and alkaline earth salts of sulfonic acids and fatty acids, organic compounds containing an acidic radical in close proximity to a nitrile, nitro, or nitroso group (e. g., alpha-cyanostearic acid), glycidyl phenyl ether, wax disulfide, etc.
Additional ingredients may comprise oil-soluble urea or thiourea derivatives, e. g., urethanes, allophanates, carbazides, carbazones, etc., polyisobutylene polymers, unsaturated polymerized esters of fatty acids and monohydric alcohols and other high-molecular-weight oil-soluble compounds.
Depending upon the additional additive used and conditions under which it is used, the amount of additive used may vary from 0.01 to 2% or higher. However, substantial; improvement is obtained by using amounts ranging from 0.1 to 0.5% in combination with the primary additive of this invention.
I claim as my invention:
1. An improved lubricant comprising a mineral lubricating oil base having incorporated therein from 0.01 to 5% by weight of tri(3-amylmercaptopropyl) phosphite.
2. An improved lubricant comprising a mineral lubricating oil base having incorporated therein from 0.01 to 5% by weight of bis(3-amylmercaptopropyl) phosphite.
3. An improved lubricant comprising a mineral lubricating oil base having incorporated therein from 0.01 to 5% by weight of tris(3-cyclohexylmercaptopropyl) phosphite.
4. An improved lubricant comprising a mineral lubricating oil base having incorporated therein from 0.01 to 5% by weight of 5-pentadecyl1nercaptopentyl phosphite.
5. An improved lubricant comprising a mineral lubricating oil base having incorporated therein from 0.01 to 5% by weight of 3-cyclophenylmercapto-2-methylpropyl phosphite.
6. An improved lubricant comprising a mineral oil base having incorporated therein a minor amount sufiicient to stabilize said oil base against oxidation deterioration of tris(3-amylmercapto propyl) phosphite. v
7. An improved lubricant comprising a mineral oil base having incorporated therein a minor amount sunicient to stabilize said oil base against oxidation deterioration of bis(3-amylmercapto propyl) phosphite.
8. An improved lubricant comprising a mineral oil base having incorporated therein a minor amount sufficient to stabilize said oil base against oxidation deterioration of tris(3-cyclohexylmercaptopropyl) phosphite.
9. An improved lubricant comprising a mineral oil base having incorporated therein a minor amount sufiicient to stabilize said oil base against oxidation deterioration of 5-pentadecyl mercaptopentyl phosphite.
10. An improved lubricant comprising a mineral oil base having incorporated therein a minor amount sufficient to stabilize said oil base against oxidation deterioration of 3-cyclopentylmercapto-2-methylpropyl phosphite.
11. An improved lubricant comprising a petroleum hydrocarbon base having incorporated therein in an amount suificient to stabilize said base against oxidation deterioration of an alkylmercaptoalkyl ester of phosphorous acid in which at least two hydrogen atoms of the acid are replaced by alkylmercaptoalkyl radicals.
12. An improved lubricant comprising a petroleum hydrocarbon base having incorporated therein in an amount sufiicient tostabilize said base against oxidation deterioration of an organic ester of phosphorous acid in which the organic radicals which replace hydrogen atoms from the hydroxyl groups of the acid have the formula RSR' in which R and R are saturated aliphatic hydrocarbon radicals, R and R containing from 1 to 15 carbon atoms.
13. An improved lubricant comprising a mineral oil base having incorporated therein in an amount sufficient to stabilize said base against oxidation deterioration of an organic ester of phosphorous acid in which the organic radicals which replace hydrogen atoms from the hydroxyl groups of the acid have the formula -RSR'- in which R and R are saturated aliphatic hydrocarbon radicals, R and R containing from 1 to 15 carbon atoms.
14. An improved lubricant comprising a petroleum hydrocarbon base having incorporated therein in an amount sufficient to stabilize said base against oxidation deterioration of an organic ester of phosphorous acid in which the organic radicals which replace hydrogen atoms from the hydroxyl groups of the acid have the formula RX-R'- in which R and R each are saturated aliphatic hydrocarbon radicals, R and R contain from 1 to 15 carbon atoms, X is an element selected from the group consisting of sulfur and selenium.
15. An improved lubricant comprising a liquid hydrocarbon lubricant base having incorporated therein in an amount suificient to stabilize said base against oxidation deterioration of an organic ester of phosphorous acid in which the organic radicals which replace hydrogen atoms from the hydroxyl groups of the acid have the formula RXR'- in which R and R each are saturated nonaromatic hydrocarbon radicals containing from 1 to 15 carbon atoms, X is an element selected from the group consisting of sulfur and selenium.
16. An improved lubricant comprising a mineral lubricating oil base, from about 0.01% to about 5%, by weight, of tris(3-amylmercapto propyl) phosphite, and from about 0.01 to about 2% of an oil-soluble calcium petroleum sulfonate.
17. An improved lubricant comprising a liquid hydrocarbon lubricant base, having incorporated therein, in an amount suflicient to stabilize said base against oxidation deterioration, an organic ester of phosphorous acid in which the organic radicals which replace hydrogen atoms of the hydroxyl groups of said acid have the formula -RXR' in which R and R each are saturated non-aromatic hydrocarbon radicals containing from 1 to 15 carbon atoms, X is an element selected from the group consisting of sulfur and selenium, and from about 0.01% to about 2% of an oil-soluble detergent.
References Cited in the file of this patent UNITED STATES PATENTS Number Name Date 2,205,021 Schuette et al. June 18, 1940 2,241,244 Conary et a1. May 6, 1941 2,371,631 Lincoln et al Mar. 20, 1945 2,372,244 Adams et a1 Mar. 27, 1945 2,373,879 Dietrich Apr. 17, 1945 2,432,095 Frey -1 Dec. 9, 1947 2,587,616 Harman Mar. 4, 1952 2,614,988 Hook et a1. -a Oct. 21, 1952
Claims (1)
17. AN IMPROVED LUBRICANT COMPRISING A LIQUID HYDROCARBON LUBRICANT BASE, HAVING INCORPORATED THEREIN, IN AN AMOUNT SUFFICIENT TO STABLIZE SAID BASE AGAINST OXIDATION DETERIORATION, AN ORGANIC ESTR OF PHOSPHOROUS ACID IN WHICH THE ORGANIC RADICALS WHICH REPLACE HYDROGEN ATOMS OF THE HYDROXYL GROUPS OF SAID ACID HAVE THE FORMULA -R-X-R'' IN WHICH R AND R'' EACH ARE SATURATED NON-AROMATIC HYDROCARBON RADICALS CONTAINING FROM 1 TO 15 CARBON ATOMS, X IS AN ELEMENT SELECTED FROM THE GROUP CONSISTING OF SULFUR AND SELENIUM, AND FROM ABOUT 0.01% TO ABOUT 2% OF AN OIL-SOLUBLE DETERGENT.
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US259015A US2685567A (en) | 1951-11-29 | 1951-11-29 | Lubricant composition containing alkyl-mercaptoalkyl phosphites |
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US259015A US2685567A (en) | 1951-11-29 | 1951-11-29 | Lubricant composition containing alkyl-mercaptoalkyl phosphites |
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Cited By (1)
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US2886526A (en) * | 1954-10-27 | 1959-05-12 | Texas Co | Ep additive for mixed lithium-calcium base greases |
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US2587616A (en) * | 1948-07-13 | 1952-03-04 | Shell Dev | Alkylmercaptoalkyl phosphites |
US2614988A (en) * | 1948-03-26 | 1952-10-21 | American Cyanamid Co | Hydrocarbon oils containing salkoxymethyl - o,o' - dialkyldithiophosphates |
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- 1951-11-29 US US259015A patent/US2685567A/en not_active Expired - Lifetime
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US2205021A (en) * | 1934-11-02 | 1940-06-18 | Ig Farbenindustrie Ag | Production of condensation products |
US2241244A (en) * | 1939-03-25 | 1941-05-06 | Texas Co | Organic phosphite compound and method of manufacturing same |
US2371631A (en) * | 1941-01-04 | 1945-03-20 | Continental Oil Co | Lubricant |
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US2432095A (en) * | 1941-12-29 | 1947-12-09 | Delton R Frey | Lubricating composition |
US2373879A (en) * | 1942-09-11 | 1945-04-17 | Du Pont | Sulphurized hydrocarbon derivatives |
US2614988A (en) * | 1948-03-26 | 1952-10-21 | American Cyanamid Co | Hydrocarbon oils containing salkoxymethyl - o,o' - dialkyldithiophosphates |
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US2886526A (en) * | 1954-10-27 | 1959-05-12 | Texas Co | Ep additive for mixed lithium-calcium base greases |
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