US2971913A - Synithetic lubricant compositions - Google Patents
Synithetic lubricant compositions Download PDFInfo
- Publication number
- US2971913A US2971913A US760867A US76086758A US2971913A US 2971913 A US2971913 A US 2971913A US 760867 A US760867 A US 760867A US 76086758 A US76086758 A US 76086758A US 2971913 A US2971913 A US 2971913A
- Authority
- US
- United States
- Prior art keywords
- hexachloro
- esters
- dimethanonaphthalene
- compositions
- base esters
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000000203 mixture Substances 0.000 title claims description 30
- 239000000314 lubricant Substances 0.000 title claims description 17
- 230000001050 lubricating effect Effects 0.000 claims description 11
- KPHOBSTVDZCCAU-UHFFFAOYSA-N tetracyclo[6.4.0.02,4.05,7]dodeca-1(12),2(4),5(7),8,10-pentaene Chemical class C1=CC=CC2=C3CC3=C(C3)C3=C21 KPHOBSTVDZCCAU-UHFFFAOYSA-N 0.000 claims description 8
- 229920003232 aliphatic polyester Polymers 0.000 claims description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 4
- 150000005690 diesters Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 description 39
- -1 aliphatic dicarboxylic acids Chemical class 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- VNTXONBESJNLBI-UHFFFAOYSA-N dinonyl decanedioate Chemical compound CCCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCCC VNTXONBESJNLBI-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 239000010687 lubricating oil Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- MDHHRPHYYRMIPH-OWEGFZGBSA-N dimethyl chlorendate Chemical compound ClC1=C(Cl)[C@@]2(Cl)[C@H](C(=O)OC)[C@H](C(=O)OC)[C@]1(Cl)C2(Cl)Cl MDHHRPHYYRMIPH-OWEGFZGBSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- DFBKLUNHFCTMDC-PICURKEMSA-N dieldrin Chemical compound C([C@H]1[C@H]2[C@@]3(Cl)C(Cl)=C([C@]([C@H]22)(Cl)C3(Cl)Cl)Cl)[C@H]2[C@@H]2[C@H]1O2 DFBKLUNHFCTMDC-PICURKEMSA-N 0.000 description 2
- 229950006824 dieldrin Drugs 0.000 description 2
- NGPMUTDCEIKKFM-UHFFFAOYSA-N dieldrin Natural products CC1=C(Cl)C2(Cl)C3C4CC(C5OC45)C3C1(Cl)C2(Cl)Cl NGPMUTDCEIKKFM-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003505 terpenes Chemical class 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- SCRQKHCVCHBBJC-UHFFFAOYSA-N 1-naphthalen-2-yl-1,2,2-triphenylhydrazine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)N(C=1C=C2C=CC=CC2=CC=1)C1=CC=CC=C1 SCRQKHCVCHBBJC-UHFFFAOYSA-N 0.000 description 1
- UNHBSPGRHLOUJZ-UHFFFAOYSA-N 2,3,4,5,6-pentaethylphenol Chemical compound CCC1=C(O)C(CC)=C(CC)C(CC)=C1CC UNHBSPGRHLOUJZ-UHFFFAOYSA-N 0.000 description 1
- BPRYUXCVCCNUFE-UHFFFAOYSA-N 2,4,6-trimethylphenol Chemical compound CC1=CC(C)=C(O)C(C)=C1 BPRYUXCVCCNUFE-UHFFFAOYSA-N 0.000 description 1
- PFEFOYRSMXVNEL-UHFFFAOYSA-N 2,4,6-tritert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PFEFOYRSMXVNEL-UHFFFAOYSA-N 0.000 description 1
- DRRDTKUTHYHEKE-UHFFFAOYSA-N 2,4-dimethyl-6-octylphenol Chemical compound CCCCCCCCC1=CC(C)=CC(C)=C1O DRRDTKUTHYHEKE-UHFFFAOYSA-N 0.000 description 1
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
- WCWCBLDWXBFHHT-UHFFFAOYSA-N 2-amino-3-benzylphenol Chemical class NC1=C(O)C=CC=C1CC1=CC=CC=C1 WCWCBLDWXBFHHT-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-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
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 239000005069 Extreme pressure additive Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- XISGXLJXEVXKER-UHFFFAOYSA-N [2,2-bis(hexanoyloxymethyl)-3-hydroxypropyl] hexanoate Chemical compound C(CCCCC)(=O)OCC(COC(CCCCC)=O)(COC(CCCCC)=O)CO XISGXLJXEVXKER-UHFFFAOYSA-N 0.000 description 1
- YRWFWADJWKDIDC-UHFFFAOYSA-N [2-(hexanoyloxymethyl)-3-pentanoyloxy-2-(pentanoyloxymethyl)propyl] hexanoate Chemical compound C(CCCC)(=O)OCC(COC(CCCCC)=O)(COC(CCCCC)=O)COC(CCCC)=O YRWFWADJWKDIDC-UHFFFAOYSA-N 0.000 description 1
- AOZDHFFNBZAHJF-UHFFFAOYSA-N [3-hexanoyloxy-2,2-bis(hexanoyloxymethyl)propyl] hexanoate Chemical compound CCCCCC(=O)OCC(COC(=O)CCCCC)(COC(=O)CCCCC)COC(=O)CCCCC AOZDHFFNBZAHJF-UHFFFAOYSA-N 0.000 description 1
- ZQYCVIGMGPFQQS-UHFFFAOYSA-N [3-pentanoyloxy-2,2-bis(pentanoyloxymethyl)propyl] pentanoate Chemical compound CCCCC(=O)OCC(COC(=O)CCCC)(COC(=O)CCCC)COC(=O)CCCC ZQYCVIGMGPFQQS-UHFFFAOYSA-N 0.000 description 1
- DARZXIQICMMEHI-UHFFFAOYSA-N [3-pentanoyloxy-2-[[3-pentanoyloxy-2,2-bis(pentanoyloxymethyl)propoxy]methyl]-2-(pentanoyloxymethyl)propyl] pentanoate Chemical compound CCCCC(=O)OCC(COC(=O)CCCC)(COC(=O)CCCC)COCC(COC(=O)CCCC)(COC(=O)CCCC)COC(=O)CCCC DARZXIQICMMEHI-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- QAFGPAJPHJHZIJ-UHFFFAOYSA-N bis(2-ethylheptyl) hexanedioate Chemical compound CCCCCC(CC)COC(=O)CCCCC(=O)OCC(CC)CCCCC QAFGPAJPHJHZIJ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- WIYAGHSNPUBKDT-UHFFFAOYSA-N dinonyl hexanedioate Chemical compound CCCCCCCCCOC(=O)CCCCC(=O)OCCCCCCCCC WIYAGHSNPUBKDT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000010688 mineral lubricating oil Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 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
- 150000002894 organic compounds Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000001681 protective effect Effects 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
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 150000003585 thioureas 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
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
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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
- C10M2205/02—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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- 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
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- 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
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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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
- C10M2207/129—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
- C10M2207/22—Acids obtained from polymerised unsaturated acids
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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- 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
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/286—Esters of polymerised unsaturated acids
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- 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
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- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/082—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type monocarboxylic
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- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
- C10M2211/042—Alcohols; Ethers; Aldehydes; Ketones
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/06—Perfluorinated compounds
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/062—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups bound to the aromatic ring
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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Definitions
- the present invention relates to extreme pressure additives for aliphatic polyester synthetic lubricants and to synthetic lubricating compositions containing such additives. It relates more particularly to the use of certain chlorinated dimethanonaphthalene derivatives.
- the lubricating oil is a synthetic material and particularly a polyester such as is formed between aliphatic dicarboxylic acids and monohydric alcohols.
- the need for such compositions is great, especially due to the advent of jet planes wherein synthetic lubricants are becoming a virtual necessity.
- compositions which are useful for improving the extreme pressure properties of lubricants are those containing chlorine, sulfur and the like.
- the difficulty with most of these compounds, whether they are effective or not, is that they are thermally unstable and decompose to yield hydrochloric acid, H 8 and the like, which in turn cause corrosion and eventual failure of the metals with which they are in contact.
- chlorinated terpenes which are thermally unstable and readily yield hydrochloric acid upon heating.
- carboxyl groups in certain terpene-like compounds provides the opportunity for formation of esters of chlorinated terpenes. have virtually no extreme pressure properties when utilized in base lubricants to the extent of fractional percentages thereof and furthermore, have substantially no effect when dispersed in ester lubricants, as will be shown a by means of comparative data given hereinafter.
- extreme pressure lubricating compositions are provided by dispersal of between about 0.2 and about 10% by weight of l,2,3,4,l0,lO-hexachloropolyhydro-dimethanonaphthalenes and/or their corresponding 6,7- epoxy, episulfido, or epi-imino derivatives, said dimethano-
- such materials r 2,971,913 Patented Feb. 14, 1961 naphthalene derivatives being dispersed in aliphatic polyester lubricants.
- the small group of compounds utilized in connection with the aliphatic polyesters may be either endo, endo; endo, exo; or exo, exo variations of the same type of molecule since the spacial configuration with respect to the plane in which the individual radicals exist does not appear to affect their utility in the present compositions. Any of the above varieties are suitable.
- the species otherwise designated (other than with respect to their spacial configurations) are as follows:
- aliphatic polyester lubricants may be generally classed as diesters, tetraesters and polyesters having a
- Typical of the diester lubricants are those formed between aliphatic dicarboxylic acids having from 4 to-12 carbon atoms per molecule with monohydric alcohols having from 6 to 18 carbonatoms per molecule, the esters containing between about 16 and 40 carbon atoms per molecule.
- Typical species include bis(Z-ethylhexylJsebacate, bis(2-ethylheptyl) adipate and didecylazealate.
- Esters based on pentaerythritol are also contemplated, which may be esters formed between aliphatic monocarboxylic acids and pentaerythritol or may be esters formed with a dimer of pentaerythritol.
- Typical species include especially those in which a mixture of fatty acids is utilized for the formation of the esters since the resulting ester mixture has a substantially lower melting point or pour point than that obtained if a single acid is utilized.
- Single species include pentaerythritol tetracaproate, pentaerythritol tetravalerate, pentaerythritol tetraheptoate, pentaerythritol dicaproate divalerate, pentaerythritol tricaproate heptoate and mixtures thereof.
- the dimers of pentaerythritol include dipentaerythritol hexacaproate, dipentaerythritol hexavalerate and mixed esters, such as dipentaerythritol tricaproate triheptoate. ployed.
- the lubricating oil employed was a synthetic diester oil being a blend of base esters consisting of 70% by weight of dinonyl sebacate, 20% by weight of dio'ctyl sebacate and 10% by weight of dinonyl adipate.
- Test samples were prepared by adding the chlorine-containing compounds to be tested to the base esters to give concentrations equivalent to 1% by weight of chlorine based on the weight of the lubricating oil.
- I.A.E. gear rig tests were performed on the base esters plus aldrin and for the sake of comparison with the base esters alone and base esters plus dioctyl chlorendate. The tests were done at 2,000 r.p.m.
- Base esters 58 Base esters+1,2,3,4,l0,10 hexachloro 1,4,4a,5,8,8a-
- the I.A.E. gear rig tests described in Example I were repeated at different temperatures with base esters plus aldrin, and for the purposes of comparison, with base esters alone and base esters plus dimethyl chlorendate. The results of these tests are given in Tzible II. The results showed that aldrin was effective in improving the extreme pressure characteristics of the base esters and was more eifective in this respect than dimethyl chlo-
- the base esters in this example were the same as those described in Example I.
- the I.A.E. g'ear rig tests described in Example I were repeated at different temperatures with base esters plus dieldrin and for the purposes of comparison, with base esters alone and base esters plus dimethyl chlorendate. The results of these tests are given in Table III. The results showed that dieldrin was effective in improving the extreme pressure characteristics of the base esters and was more effective in this respect than dimethyl chlorendate.
- the tests in this example were performed at 4000 r.p.m.
- Compositions of this invention may contain minor proportions of other lubricating oil additives, such as antioxidants, corrosion inhibitors or anti-rusting compounds, wear reducing agents, blooming agents, pour point depressants, viscosity improvers and anti-foaming agents.
- other lubricating oil additives such as antioxidants, corrosion inhibitors or anti-rusting compounds, wear reducing agents, blooming agents, pour point depressants, viscosity improvers and anti-foaming agents.
- Anti-oxidants which may be used comprise several types, for example, alkyl phenols, such as 2,4,6-trimethyl phenol, pentaethyl phenol, 2,4-dimethyl-6-tertiary-butyi phenol, 2,4-dimethyl-6-octyl phenol, 2,6-ditertiary-butyl- 4-methyl phenol and 2,4,6-tritertiary-butyl phenol, amino phenols, such as benzyl amino phenols and amines-such as dibutylphenylene diamine, diphenylamino, N-phenylbeta-naphthylamine, N-phenyl-alpha-naphthylzirnine' and dinaphthylamine.
- alkyl phenols such as 2,4,6-trimethyl phenol, pentaethyl phenol, 2,4-dimethyl-6-tertiary-butyi phenol, 2,4-dimethyl
- Suitable corrosion inhibitors or anti-rusting compounds which may be used are the dicarboxylic acids having 16 or more carbon atoms in the molecule and organic compounds containing acidic radicals in close proximity to a nitrile, nitro or nitroso group, for example, alpha cyano stearic acid.
- Wear reducing agents which may be used comprise esters of phosphorus acids, such as triaryl, alkaryl or aralkyl phosphates, thiophosphates or phosphites' and neutral aromatic sulfur compounds of relatively high boiling point, such as diaryl sulfides, diaryl disulfides, alkyl aryl disulfides, for example, diphcnyl sulfide, diphenol sulfide, dicresol sulfide, dixylenol sulfide, methyl butyl diphenol sulfide, dibenzyl sulfide and the corresponding diand tri-sulfides.
- esters of phosphorus acids such as triaryl, alkaryl or aralkyl phosphates, thiophosphates or phosphites' and neutral aromatic sulfur compounds of relatively high boiling point
- diaryl sulfides diaryl disulfides, alkyl aryl disulfides, for example, diphc
- dimethyl silicone polymer As an example of a suitable anti-foaming agent dimethyl silicone polymer can be mentioned. Additional ingredients may comprise oil-soluble urea or thiourea derivatives, for example, urethanos, allophanates, carbazides and carbazcne, polyisobutylene polymers and polymerized unsaturated esters of fatty acids and 'monohydric alcohols.
- oil-soluble urea or thiourea derivatives for example, urethanos, allophanates, carbazides and carbazcne, polyisobutylene polymers and polymerized unsaturated esters of fatty acids and 'monohydric alcohols.
- a lubricating composition comprising a major proportion of dinonyl sebacate and between about 0.2% and about 10% by weight of. 1,2,3,4,10,10-hexachlorol,4,4a,5,8,8a-hexahydrocndo-1,4 eXo 5,8 dimethanonaphthalene.
- a lubricating composition comprising a major proportion of dinonyl sebacate and between about 0.2% and about 10% by weight of 1,2,3,4,l0,l0-hexachloro- 6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro endo -'1,4-exo-5 .8- dimethanonaphthalene.
- a lubricating composition comprising a major proportion of dinonyl sebacate and between about'0.2% and about 10% by weight of l,2,3,4,10,10-hexachloro- 1,4,4a,5,8,8a-hexahydro-endo-1,4-endo 5,8 dimethanonaphthalene.
- a lubricating composition comprising a major proportion of dinonyl sebacate and between about 0.2% and about 10% by weight of 1',2,3,4,l0,l0-hexachloro- 6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro endo l,4-endo- 5,8-dimethanonaphthalcne.
- a lubricating composition comprising a major. proportion of an'oleaginous ester of an aliphatic dicarboxylic acid and an aliphatic monohydric alcohol, said ester containing between about 16 and 40 carbon atoms per molecule and between about 0.2% and about 10% by weight of an unsubstituted 1,2,3,4,10,10-hexachloro-L4,
- a lubricating composition comprising a major proportion of an oleaginous ester of an aliphatic diearboxylic acid and an aliphatic monohydric alcohol, said ester containing between about 16 and 40 carbon atoms per molecule and between about 0.2% and about 10% by weight of an unsubstituted 1,2,3,4,10,10-6,7-epoxyhexachloro-1,4,4a,5,6,7,8,8a-octahydro 1,4,5,8-dimethanonaphthalene.
- a lubricating composition comprising a major proportion of an oleaginous ester of an aliphatic dicarboxylic acid and an aliphatic monohydric alcohol, said ester containing between about 16 and 40 carbon atoms per molecule and between about 0.2% and about 10% by weight of a chlorinated dimethanonaphthalene of the group consisting of 1,2,3,4,10,10-hexachloro-I,4,4a,5,8, 8a-hexahydro-1,4,5,8-dimethanonaphthalenes, 1,2,3,4,10, 10-hexachloro-6,7-epi-1,4,4a,5,6,6,7,8,8a-octahydro 1,4,
- epi is an epatomic 20 radical of the group consisting of epoxy, episulfido and epi-imino, and mixtures thereof.
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Description
SYNTHETIC LUBRICANT COMPOSITIONS Vernon W. David, Chester, and Fnnc'u H. Waight, Wirral, England, assignors to Shell Oil Company, a corporation of Delaware No Drawing. Filed Sept. '15, 1958, Ser. No. 760,867
8 Claims. (Cl. 252-484) The present invention relates to extreme pressure additives for aliphatic polyester synthetic lubricants and to synthetic lubricating compositions containing such additives. It relates more particularly to the use of certain chlorinated dimethanonaphthalene derivatives.
It is well known that the high pressures occurring in certain types of gears and bearings may cause a film of lubricant to rupture with consequent damage to machinery or engines. It has been shown that mineral oils can be improved with regard to their protective effect upon rubbing surfaces by the addition of a wide variety of certain substances so that excessive wear, scuffing, seizure and the like which normally follow a break in the film of lubricant can be prevented even under very unfavorable pressure and speed conditions. Lubricants possessing this highly desirable property are called extreme pressure lubricants. While many substances improve mineral lubricating oils in this respect, exceeding few compounds have been found which are effective for the same purpose when the lubricating oil is a synthetic material and particularly a polyester such as is formed between aliphatic dicarboxylic acids and monohydric alcohols. The need for such compositions is great, especially due to the advent of jet planes wherein synthetic lubricants are becoming a virtual necessity.
Many compositions which are useful for improving the extreme pressure properties of lubricants are those containing chlorine, sulfur and the like. However, the difficulty with most of these compounds, whether they are effective or not, is that they are thermally unstable and decompose to yield hydrochloric acid, H 8 and the like, which in turn cause corrosion and eventual failure of the metals with which they are in contact. This is true even of such materials as chlorinated terpenes, which are thermally unstable and readily yield hydrochloric acid upon heating. The presence of carboxyl groups in certain terpene-like compounds provides the opportunity for formation of esters of chlorinated terpenes. have virtually no extreme pressure properties when utilized in base lubricants to the extent of fractional percentages thereof and furthermore, have substantially no effect when dispersed in ester lubricants, as will be shown a by means of comparative data given hereinafter.
It is an object of the present invention to provide improved lubricating compositions. It is a further object of this invention to provide improved aliphatic polyester lubricants. It is a'particular object of the present invention to provide aliphatic polyester lubricant compositions showing surprisingly effective extreme pressure properties. Other objects will become apparent during the following description of the invention.
Now, in accordance with the present invention, it has been found that extreme pressure lubricating compositions are provided by dispersal of between about 0.2 and about 10% by weight of l,2,3,4,l0,lO-hexachloropolyhydro-dimethanonaphthalenes and/or their corresponding 6,7- epoxy, episulfido, or epi-imino derivatives, said dimethano- However, such materials r 2,971,913 Patented Feb. 14, 1961 naphthalene derivatives being dispersed in aliphatic polyester lubricants.
The small group of compounds utilized in connection with the aliphatic polyesters may be either endo, endo; endo, exo; or exo, exo variations of the same type of molecule since the spacial configuration with respect to the plane in which the individual radicals exist does not appear to affect their utility in the present compositions. Any of the above varieties are suitable. The species otherwise designated (other than with respect to their spacial configurations) are as follows:
1,2,3,4,10,10 hexachloro 1,4,4a,5,8,8a-hexahydromethanonaphthalenes 1,2,3,4,10,10-hexachloro 6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydrodimethanonaphthalenes 1,2,3,4,10,10 hexachloro-6,7-episulfido 1,4,4a,5,6,7,8,8a-
octahydrodimethanonaphthalenes 12,3,4,l0,10 hexachloro-6,7-imino-1,4,4a,5,6,7,8,8a-octahydrodimethanonaphthalenes The following four species defined still further with respect to their spacial configuration are those particularly preferred for use in the subject compositions:
1,2,3,4,l0,10 hexachloro 1,4,4a,5,8,8a-hexahydro-endol,4-exo-5,S-dimethanonaphthalene 1,2,3,4,10,l0 hexachloro-6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro-endo-l,4-exo-5,B-dimethanonaphthalene 1,2,3,4,10,10 hexachloro 1,4,4a,5,8,8a-hexahydro-endol,4-endo-5,8-dimethanonaphthalene 1,2,3,4,10,10 hexachloro-6,7-epoxy 1,4,4a,5,7,8,8a-octahydro-endo-I,4-endo-5,S-dimethanonaphthalene The aliphatic polyester lubricants may be generally classed as diesters, tetraesters and polyesters having a greater number of ester linkages. Typical of the diester lubricants are those formed between aliphatic dicarboxylic acids having from 4 to-12 carbon atoms per molecule with monohydric alcohols having from 6 to 18 carbonatoms per molecule, the esters containing between about 16 and 40 carbon atoms per molecule. Typical species include bis(Z-ethylhexylJsebacate, bis(2-ethylheptyl) adipate and didecylazealate. Esters based on pentaerythritol are also contemplated, which may be esters formed between aliphatic monocarboxylic acids and pentaerythritol or may be esters formed with a dimer of pentaerythritol. Typical species include especially those in which a mixture of fatty acids is utilized for the formation of the esters since the resulting ester mixture has a substantially lower melting point or pour point than that obtained if a single acid is utilized. Single species include pentaerythritol tetracaproate, pentaerythritol tetravalerate, pentaerythritol tetraheptoate, pentaerythritol dicaproate divalerate, pentaerythritol tricaproate heptoate and mixtures thereof. The dimers of pentaerythritol include dipentaerythritol hexacaproate, dipentaerythritol hexavalerate and mixed esters, such as dipentaerythritol tricaproate triheptoate. ployed.
Of course, mixtures of'esters may be em- EXAMPLE I The lubricating oil employed was a synthetic diester oil being a blend of base esters consisting of 70% by weight of dinonyl sebacate, 20% by weight of dio'ctyl sebacate and 10% by weight of dinonyl adipate. Test samples were prepared by adding the chlorine-containing compounds to be tested to the base esters to give concentrations equivalent to 1% by weight of chlorine based on the weight of the lubricating oil. I.A.E. gear rig tests were performed on the base esters plus aldrin and for the sake of comparison with the base esters alone and base esters plus dioctyl chlorendate. The tests were done at 2,000 r.p.m. and at 60 C. Two tests were performed on each oil, using 4-pint samples at tit-pint per minute flow rate and the results of these tests are given in Table I. The results showed that the dioctyl chlorendate had no beneficial effect on the extreme pressure characteristics of the base esters whereas aldrin and hexachlorocyclopentadiene were effective in improving the extreme pressure characteristics of the base esters.
Table I Mean scuffing load in lbs. Base esters 58 Base esters+1,2,3,4,l0,10 hexachloro 1,4,4a,5,8,8a-
hexahydro-endo-1,4-exo-5,S-dimethanonaphthalene- 75 Base esters+dioctyl chlorendate 50 EXAMPLE II The base esters in this example were the same as those described in Example I.
The I.A.E. gear rig tests described in Example I were repeated at different temperatures with base esters plus aldrin, and for the purposes of comparison, with base esters alone and base esters plus dimethyl chlorendate. The results of these tests are given in Tzible II. The results showed that aldrin was effective in improving the extreme pressure characteristics of the base esters and was more eifective in this respect than dimethyl chlo- The base esters in this example were the same as those described in Example I. The I.A.E. g'ear rig tests described in Example I were repeated at different temperatures with base esters plus dieldrin and for the purposes of comparison, with base esters alone and base esters plus dimethyl chlorendate. The results of these tests are given in Table III. The results showed that dieldrin was effective in improving the extreme pressure characteristics of the base esters and was more effective in this respect than dimethyl chlorendate. The tests in this example were performed at 4000 r.p.m.
Compositions of this invention may contain minor proportions of other lubricating oil additives, such as antioxidants, corrosion inhibitors or anti-rusting compounds, wear reducing agents, blooming agents, pour point depressants, viscosity improvers and anti-foaming agents.
Anti-oxidants which may be used comprise several types, for example, alkyl phenols, such as 2,4,6-trimethyl phenol, pentaethyl phenol, 2,4-dimethyl-6-tertiary-butyi phenol, 2,4-dimethyl-6-octyl phenol, 2,6-ditertiary-butyl- 4-methyl phenol and 2,4,6-tritertiary-butyl phenol, amino phenols, such as benzyl amino phenols and amines-such as dibutylphenylene diamine, diphenylamino, N-phenylbeta-naphthylamine, N-phenyl-alpha-naphthylzirnine' and dinaphthylamine.
Examples of suitable corrosion inhibitors or anti-rusting compounds which may be used are the dicarboxylic acids having 16 or more carbon atoms in the molecule and organic compounds containing acidic radicals in close proximity to a nitrile, nitro or nitroso group, for example, alpha cyano stearic acid.
Wear reducing agents which may be used comprise esters of phosphorus acids, such as triaryl, alkaryl or aralkyl phosphates, thiophosphates or phosphites' and neutral aromatic sulfur compounds of relatively high boiling point, such as diaryl sulfides, diaryl disulfides, alkyl aryl disulfides, for example, diphcnyl sulfide, diphenol sulfide, dicresol sulfide, dixylenol sulfide, methyl butyl diphenol sulfide, dibenzyl sulfide and the corresponding diand tri-sulfides. v r,
As an example of a suitable anti-foaming agent dimethyl silicone polymer can be mentioned. Additional ingredients may comprise oil-soluble urea or thiourea derivatives, for example, urethanos, allophanates, carbazides and carbazcne, polyisobutylene polymers and polymerized unsaturated esters of fatty acids and 'monohydric alcohols.
One of the advantages gained by the use of the present invention especially when the epi derivatives of dimethanonaphthalene are employed is the surprisinglylow corrosion caused by the compositions. Even though the recited class of chlorinated dimethanonaphthalene is abnormally stable under high temperature conditions, nonetheless any chlorinated compound can be expected to release at least trace amounts of chlorine-or chlorine derivatives. These can be expected to be, corrosive in nature andhence it is preferred practice to provide for a chlorine acceptor such as an epoxide or similar compounds. Thus, it will be seen by a study-.of the compounds involved in the present compositions that'a builtin chlorine acceptor is present within the molecule. When the epi compounds are employedeitheras the sole extreme pressure agent or in addition to'one-of theother dimethanonaphthalene chlorinated compounds with which the present invention is concerned. This feature distinguishes the present compositions from those knownin the prior art in that the extreme pressure'agent-may also constitute a chlorine'acc'eptor if the latter is released during the use of the compositions involved.
We claim as our invention: 1. A lubricating composition comprising a major proportion of dinonyl sebacate and between about 0.2% and about 10% by weight of. 1,2,3,4,10,10-hexachlorol,4,4a,5,8,8a-hexahydrocndo-1,4 eXo 5,8 dimethanonaphthalene.
2. A lubricating composition comprising a major proportion of dinonyl sebacate and between about 0.2% and about 10% by weight of 1,2,3,4,l0,l0-hexachloro- 6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro endo -'1,4-exo-5 .8- dimethanonaphthalene. I
3. A lubricating composition comprising a major proportion of dinonyl sebacate and between about'0.2% and about 10% by weight of l,2,3,4,10,10-hexachloro- 1,4,4a,5,8,8a-hexahydro-endo-1,4-endo 5,8 dimethanonaphthalene.
4. A lubricating composition comprising a major proportion of dinonyl sebacate and between about 0.2% and about 10% by weight of 1',2,3,4,l0,l0-hexachloro- 6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro endo l,4-endo- 5,8-dimethanonaphthalcne.
5. A lubricating composition comprising a major. proportion of an'oleaginous ester of an aliphatic dicarboxylic acid and an aliphatic monohydric alcohol, said ester containing between about 16 and 40 carbon atoms per molecule and between about 0.2% and about 10% by weight of an unsubstituted 1,2,3,4,10,10-hexachloro-L4,
4a,5,8,8a-hexahydro-1,4,5,8'dirnethanonaphthalene.
6. A lubricating composition comprising a major proportion of an oleaginous ester of an aliphatic diearboxylic acid and an aliphatic monohydric alcohol, said ester containing between about 16 and 40 carbon atoms per molecule and between about 0.2% and about 10% by weight of an unsubstituted 1,2,3,4,10,10-6,7-epoxyhexachloro-1,4,4a,5,6,7,8,8a-octahydro 1,4,5,8-dimethanonaphthalene.
7. A lubricating composition comprising a major proportion of an oleaginous ester of an aliphatic dicarboxylic acid and an aliphatic monohydric alcohol, said ester containing between about 16 and 40 carbon atoms per molecule and between about 0.2% and about 10% by weight of a chlorinated dimethanonaphthalene of the group consisting of 1,2,3,4,10,10-hexachloro-I,4,4a,5,8, 8a-hexahydro-1,4,5,8-dimethanonaphthalenes, 1,2,3,4,10, 10-hexachloro-6,7-epi-1,4,4a,5,6,6,7,8,8a-octahydro 1,4,
5,8-dimethanonaphthalenes, wherein epi is an epatomic 20 radical of the group consisting of epoxy, episulfido and epi-imino, and mixtures thereof.
References Cited in the file of this patent UNITED STATES PATENTS 2,635,979 Lidov Apr. 21, 1953 FOREIGN PATENTS 451,411 Great Britain July 29, 1936 453,047 Great Britain Aug. 31, 1936 OTHER REFERENCES Lubrication Engineering, August 1952, pp. 177-179.
Claims (1)
- 8. A LUBRICATING COMPOSITION COMPRISING A MAJOR PROPORTION OF AN OLEAGINOUS ALIPHATIC POLYESTER LUBRICANT OF THE GROUP CONSISTING OF ALIPHATIC DIESTERS AND ESTERS OF PENTAERYTHRITOL AND BETWEEN ABOUT 0.2% AND ABOUT 10% OF A CHLORINATED DIMETHANONAPHTHALENE OF THE GROUP CONSISTING OF 1,2,3,4,10,10-HEXACHLORO-1,4,4A,5,8,8A-HEXAHYDRO - 1,4,5,8 - DIMENTHANONAPHTHALENE, 1,2,3,4,10,10-HEXACHLORO-6,7-EPI-1,4,4A,5,6,6,7,8,8A-OCTAHYDRO - 1,4,5,8 - DIMETHANONAPHTHALENES, WHEREIN EPI IS AN EPATOMIC RADICAL OF THE GROUP CONSISTING OF EPOXY, EPISULFIDO AND EPI-EMINO, AND MIXTURES THEREOF.
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US760867A US2971913A (en) | 1958-09-15 | 1958-09-15 | Synithetic lubricant compositions |
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Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3088911A (en) * | 1961-11-09 | 1963-05-07 | Exxon Research Engineering Co | Lubricant containing ashless antiwear additives |
US3121738A (en) * | 1962-05-21 | 1964-02-18 | Standard Oil Co | Hexachlorocyclopentadiene derivatives |
US3124533A (en) * | 1964-03-10 | Fluorine containing esters of poly- | ||
US3125531A (en) * | 1964-03-17 | Certificate of correction | ||
US3157600A (en) * | 1961-04-06 | 1964-11-17 | Sinclair Research Inc | Synthetic ester lubricant containing a polyester of chlorendic acid |
US3158575A (en) * | 1958-06-13 | 1964-11-24 | Texaco Inc | Calcium base greases containing chlorinated bicycloheptene compounds |
US3179592A (en) * | 1963-03-20 | 1965-04-20 | Diamond Alkali Co | Lubricant containing bis (trichloromethyl) benzene |
US3219581A (en) * | 1962-02-12 | 1965-11-23 | Sinclair Research Inc | Extreme pressure complex grease |
US3247114A (en) * | 1962-05-21 | 1966-04-19 | Standard Oil Co | Lubricating compositions containing hexachlorocyclopentadiene derivatives |
US4755310A (en) * | 1986-06-02 | 1988-07-05 | Shin-Etsu Chemical Co., Ltd. | Silicone grease composition containing a chlorinated alicyclic compound |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB451411A (en) * | 1934-12-29 | 1936-07-29 | Carl Frederick Prutton | Improvements relating to lubricants and to lubrication |
US2635979A (en) * | 1947-12-31 | 1953-04-21 | Shell Dev | Polycyclic insect toxicants |
-
1958
- 1958-09-15 US US760867A patent/US2971913A/en not_active Expired - Lifetime
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB451411A (en) * | 1934-12-29 | 1936-07-29 | Carl Frederick Prutton | Improvements relating to lubricants and to lubrication |
GB453047A (en) * | 1934-12-29 | 1936-08-31 | Carl Frederick Prutton | Improvements relating to lubricants and to lubrication |
US2635979A (en) * | 1947-12-31 | 1953-04-21 | Shell Dev | Polycyclic insect toxicants |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3124533A (en) * | 1964-03-10 | Fluorine containing esters of poly- | ||
US3125531A (en) * | 1964-03-17 | Certificate of correction | ||
US3158575A (en) * | 1958-06-13 | 1964-11-24 | Texaco Inc | Calcium base greases containing chlorinated bicycloheptene compounds |
US3157600A (en) * | 1961-04-06 | 1964-11-17 | Sinclair Research Inc | Synthetic ester lubricant containing a polyester of chlorendic acid |
US3088911A (en) * | 1961-11-09 | 1963-05-07 | Exxon Research Engineering Co | Lubricant containing ashless antiwear additives |
US3219581A (en) * | 1962-02-12 | 1965-11-23 | Sinclair Research Inc | Extreme pressure complex grease |
US3121738A (en) * | 1962-05-21 | 1964-02-18 | Standard Oil Co | Hexachlorocyclopentadiene derivatives |
US3247114A (en) * | 1962-05-21 | 1966-04-19 | Standard Oil Co | Lubricating compositions containing hexachlorocyclopentadiene derivatives |
US3179592A (en) * | 1963-03-20 | 1965-04-20 | Diamond Alkali Co | Lubricant containing bis (trichloromethyl) benzene |
US4755310A (en) * | 1986-06-02 | 1988-07-05 | Shin-Etsu Chemical Co., Ltd. | Silicone grease composition containing a chlorinated alicyclic compound |
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