US2735816A - Fluid compositions containing an - Google Patents
Fluid compositions containing an Download PDFInfo
- Publication number
- US2735816A US2735816A US2735816DA US2735816A US 2735816 A US2735816 A US 2735816A US 2735816D A US2735816D A US 2735816DA US 2735816 A US2735816 A US 2735816A
- Authority
- US
- United States
- Prior art keywords
- orthosilicate
- grease
- ester
- aliphatic
- aromatic
- 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 52
- 239000012530 fluid Substances 0.000 title claims description 20
- 239000000344 soap Substances 0.000 claims description 44
- 229910052751 metal Inorganic materials 0.000 claims description 40
- 239000002184 metal Substances 0.000 claims description 40
- BPQQTUXANYXVAA-UHFFFAOYSA-N silicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 38
- 239000007788 liquid Substances 0.000 claims description 26
- 238000009835 boiling Methods 0.000 claims description 12
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 8
- -1 hydoxy Chemical group 0.000 description 86
- 239000003963 antioxidant agent Substances 0.000 description 40
- 235000006708 antioxidants Nutrition 0.000 description 40
- 239000004519 grease Substances 0.000 description 40
- 125000001931 aliphatic group Chemical group 0.000 description 26
- 230000003647 oxidation Effects 0.000 description 26
- 238000007254 oxidation reaction Methods 0.000 description 26
- 125000000217 alkyl group Chemical group 0.000 description 24
- 230000003078 antioxidant Effects 0.000 description 24
- 125000003118 aryl group Chemical group 0.000 description 22
- 150000002148 esters Chemical class 0.000 description 22
- 150000004762 orthosilicates Chemical class 0.000 description 20
- 230000000111 anti-oxidant Effects 0.000 description 16
- 239000010696 ester oil Substances 0.000 description 16
- ADLSSRLDGACTEX-UHFFFAOYSA-N tetraphenyl silicate Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 ADLSSRLDGACTEX-UHFFFAOYSA-N 0.000 description 14
- 229910052605 nesosilicate Inorganic materials 0.000 description 12
- 125000004432 carbon atoms Chemical group C* 0.000 description 10
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 229940116351 sebacate Drugs 0.000 description 10
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 10
- KKZOJPJHWKWAID-UHFFFAOYSA-N tetracyclohexyl silicate Chemical compound C1CCCCC1O[Si](OC1CCCCC1)(OC1CCCCC1)OC1CCCCC1 KKZOJPJHWKWAID-UHFFFAOYSA-N 0.000 description 10
- HGPXWXLYXNVULB-UHFFFAOYSA-M Lithium stearate Chemical class [Li+].CCCCCCCCCCCCCCCCCC([O-])=O HGPXWXLYXNVULB-UHFFFAOYSA-M 0.000 description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- 150000001342 alkaline earth metals Chemical class 0.000 description 6
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- KUUNNVBBPBDFJZ-UHFFFAOYSA-N 1-dodecylselanyldodecane Chemical compound CCCCCCCCCCCC[Se]CCCCCCCCCCCC KUUNNVBBPBDFJZ-UHFFFAOYSA-N 0.000 description 4
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-Ethylhexanol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N Catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N Phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 4
- 229950000688 Phenothiazine Drugs 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 229910052788 barium Inorganic materials 0.000 description 4
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium(0) Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000000875 corresponding Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 230000001050 lubricating Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 4
- 229910052712 strontium Inorganic materials 0.000 description 4
- 230000000153 supplemental Effects 0.000 description 4
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 2
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 2
- MVRPPTGLVPEMPI-UHFFFAOYSA-N 2-cyclohexylphenol Chemical compound OC1=CC=CC=C1C1CCCCC1 MVRPPTGLVPEMPI-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N Azelaic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 229940067597 Azelate Drugs 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N Behenic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- MULPNGNCJCZZLB-UHFFFAOYSA-N C(CCCCC)(=O)OC(C)CC(C)OC(CCCCC)=O Chemical compound C(CCCCC)(=O)OC(C)CC(C)OC(CCCCC)=O MULPNGNCJCZZLB-UHFFFAOYSA-N 0.000 description 2
- DPUOLQHDNGRHBS-KTKRTIGZSA-N Erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 2
- 229910004664 ORa Inorganic materials 0.000 description 2
- 241000658540 Ora Species 0.000 description 2
- 206010040003 Sensation of pressure Diseases 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N Thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- 239000005844 Thymol Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical group C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 229940093476 ethylene glycol Drugs 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000006501 nitrophenyl group Chemical group 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 125000004430 oxygen atoms Chemical group O* 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000004351 phenylcyclohexyl group Chemical group C1(=CC=CC=C1)C1(CCCCC1)* 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 230000000750 progressive Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003346 selenoethers Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000010689 synthetic lubricating oil Substances 0.000 description 2
- 229960000790 thymol Drugs 0.000 description 2
- 229930007823 thymol Natural products 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N tin hydride Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 230000003245 working Effects 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
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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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M7/00—Solid or semi-solid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single solid or semi-solid substances
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- 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
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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
- C10M2207/28—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
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
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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
- C10M2215/064—Di- and triaryl amines
- C10M2215/065—Phenyl-Naphthyl amines
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/108—Phenothiazine
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- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/02—Esters of silicic acids
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
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- C10N2010/00—Metal present as such or in compounds
- C10N2010/02—Groups 1 or 11
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- C10N2010/04—Groups 2 or 12
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- C10N2010/00—Metal present as such or in compounds
- C10N2010/06—Groups 3 or 13
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- C10N2010/00—Metal present as such or in compounds
- C10N2010/08—Groups 4 or 14
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
Definitions
- This invention relates to new fluid compositions having lubricating properties, more particularly to improved aliphatic ester oils and greases.
- the aliphatic ester oils to which reference is made herein and with which the present invention is concerned are liquid saturated aliphatic normal esters of saturated aliphatic carboxylic acids which esters are further defined by the fact that their boiling point is 150 C. or higher.
- This class of liquid aliphatic esters has been recognized by the art as a source of synthetic lubricating oils and some of these esters have been used with metal soaps for making greases. The art is also aware that metal soaps accelerate the thermal oxidation of these liquid aliphatic esters and has added antioxidants to the greases to improve their oxidation stability.
- the present invention has an object the provision of a new class of antioxidants for improving the oxidation stability of the aliphatic ester oils which contain metal soaps, especially at elevated temperatures.
- a further object is the provision of aliphatic ester oil greases which have enhanced oxidation stability at elevated temperatures.
- orthosilicate antioxidants of the present invention contain an aromatic or hydroaromatic group on each of at least two of the ester oxygen atoms of the molecule, with a lower alkyl group being attached to such of the ester oxygen atoms as are not satisfied by an aromatic or hydroaromatic group.
- R, R1, R2 and R3 each represent an aromatic or a hydroaromatic radical, or in part represent a lower alkyl radical of up to 6 carbon atoms where only two or three of the ester oxygen atoms of the orthosilicate molecule are attached to an aromatic or hydroaromatic radical.
- the radicals R, R1, R2 and R3 may be the same or different aromatic and hydroaromatic groups and the same or difierent lower alkyl groups where two such are present in the orthosilicate molecule.
- the radicals R, R1, R2 and R3 may be aryl or hydroaryl groups which may be substituted or not by groups such as, for example, alkyl, cycloalkyl, aralkyl, alkoxy, aryloxy, hydoxy, carboxy, carbalkoxy, nitro, amino, alkylamino, arylamino, etc., groups.
- the aromatic radical of the ortho-silicates may be, for example, phenyl, naphthyl, diphenyl, tolyl, xylyl, cyclohexylphenyl, benzylphenyl, anisyl, phenoxyphenyl, hydroxyphenyl, carboxyphenyl, carbethoxyphenyl, nitrophenyl, aminophenyl, N-methyli d States Patent 9 1 aromatic radical of the orthosilicates may be, for exby weight.
- group attached to the oxygen atom of the orthosilicate molecule is a lower alkyl radical the same may be, for example, methyl, ethyl, propyl, butyl, tertiary butyl, hexyl, etc.
- Illustrative orthosilicate compounds coming within the above general formula are, for example, tetraphenyl orthosilciate, tetra-o-tolyl orthosilicate, tetradiphenyl orthosilicate, tetra-B-naphthyl orthosilicate, tetracyclohexyl orthosilicate, di-methyl-di-phenyl orthosilicate, methyl-tri-phenyl orthosilicate and ethyl-tri-o-tolyl orthosilicate.
- a preferred class of the orthosilicate compounds as antioxidants for the new fluid compositions are those in which the aromatic and hydroaromatic groups are attached to the ester oxygen atoms of the orthosilicate molecule are monoor dinuclear and more preferably are monoand dinuclear aryl and hydroaryl groups which may or may not contain lower alkyl groups, for example, methyl, ethyl, isopropyl, butyl, tertiary butyl, hexyl, etc., groups.
- this preferred group of orthosilicate compounds is to be mentioned in partciular, tetraphenyl orthosilicate and tetracyclohexyl orthosilicate.
- the stability to oxidation, especially at elevated temperatures, e. g. at to C., of the aliphatic ester oil-metal soap compositions can be enhanced by the addition thereto of one of the antioxidant orthosilicates in concentrations within the range of about 0.1 and 10% by weight therein, with a preferred general range for the addition of the antioxidant being from about 0.1 to 5%
- the amount of the antioxidant added will depend upon the activity of the individual orthosilicates and the particular aliphatic ester oil-metal soap composition.
- the orthosilicate compound is dissolved or dispersed in the aliphatic ester oil depending upon its solubility therein.
- the aliphatic ester oils of the compositions of the invention may be prepared by complete esterification in known way between the corresponding saturated aliphatic carboxylic acids, for example, butyric, oxalic, adipic, 3- methyladipic, azelaic, tricarballylic acids, etc., and the corresponding saturated aliphatic alcohols, for example, methanol, 2-ethylhexanol, ethyleneglycol, glycerol, pentaethrythritol, etc.; the acids and the alcohols being selected so as to obtain the desired liquid normal ester as will be understood by those skilled in the art.
- a class of esters of particular interest for the compositions of the present invention are the liquid saturated aliphatic diesters of the saturated aliphatic dicarboxylic acids which.
- alkylene chain of 3 or more carbon atoms, more especially those which are straight or branched chain alkyl diesters of the 5 to 12 carbon atom alkylene dicarboxylic acids in which the alkylene chain may be branched or unbranched and which have the general formula:
- the metal soap in the compositions of the invention may be any of the metal salts of the soap-forming fatty and hydroxy fatty acids, for example, the calcium, strontium, barium, sodium, potassium, lithium, copper, tin,
- the metal soap in the compositions may be widely varied and range from as little as about 0.1% by weight up to a practical maximum.
- the metal soap content of the compositions will generally be from about to 30% by weight, for which usually there is employed one of the alkaline earth or alkali metal soaps, for example, calcium, strontium, barium, sodium and lithium stearates.
- the invention is illustrated in greater detail by the following specific examples in which the orthosilicate compound was incorporated in a lithium soap-diester grease and subjected to an accelerated oxidation test to determine its efiicacy as an antioxidant for the metal soap-diester oil composition at elevated temperatures.
- the greases were prepared in conventional manner by heating the aliphatic ester oil and metal soap together under stirring to form a clear solution, quickly cooling the solution to form a gel and working the gel through a screen to obtain a grease of uniform consistency (about workings through a Hain Microworker).
- the antioxidant was mixed into the grease and the whole then worked through the screen as before to obtain uniformity of admixture.
- control grease or blank was made up to contain the same relative proportion of the metal soap and diester oil in each instance but without the presence of the orthosilicate anti-oxidant.
- the accelerated oxidation tests were carried out in accordance with Navy Specification ANG-3a(2) using a Norma-Holiman bomb apparatus.
- Example 1 A grease was prepared to contain 16.2 mol percent (11.12% by weight) lithium stearate, 80.8 mol percent (87.68% by weight) di-Z-ethylhexyl sebacate and 3.0 mol percent (1.2% by weight) tetraphenyl orthosilicate.
- a control grease was made up in the same manner to contain only lithium stearate and di-Z-ethylhexyl sebacate in the same relative proportions.
- Example 2 The oxidation test of Example 1 was applied concurrently to a like grease containing 3 mol percent tetracyclohexyl orthosilicate in place of the tetraphenyl orthosilicate, using the same constant temperature bath to heat the bomb. Bomb pressure readings showed only a very small drop in pressure over the period of 300 hours, approximately 2 to 3 p. s. i., indicating the tetracyclohexyl orthosilicate to be also a particularly effective antioxidant for the grease.
- Example 3 A grease was made up to contain 12% by weight lithium stearate, 3.2% by weight tetraphenyl orthosilicate and the remainder di-Z-ethylhexyl sebacate was subjected to the like oxidation test as in Example 1 but at a temperature of 150 C., and for a period of 20 hours.
- the grease containing the tetraphenyl orthosilicate showed an 8.0 p. s. i. drop in oxygen pressure after 20 hours whereas the control for the same period showed a drop of 57 p. s. i. oxygen pressure, indicating the orthosilicate compound to be an effective antioxidant for the grease at 150 C.
- the aliphatic ester oil-metal soap compositions of the present invention maybe blended with miscible proportions of other lubricating oils, such as petroleum oils and polyoxyalkylene oxides having one or both terminals ending in an alkyl other group, e. g., the butoxy group.
- Antioxidants of types other than the orthosilicates may be used in the compositions in conjunction with the tetraaromatic and tetrahydroaromatic orthosilicate antioxidants, such as phenolic and aromatic amine type antioxidants which are active as antioxidants at the lower temperatures, e. g.
- antioxidant compounds of the non-silicate type are dialkyl selenides, e. g., dilauryl selenide, and phenothiazine. Some of these supplemental antioxidant compounds are active, at the elevated temperatures also, for example, dilauryl selenide and phenothiazine.
- a fluid composition comprising a liquid saturated aliphatic normal ester of a saturated aliphatic carboxylic acid, which ester has a boiling point not lower than C., a metal. soap, and a small amount of an orthosilicate of the general formula:
- R, R1, R2 and Rs are selected from the group consisting of lower alkyl radicals having up to 6 carbon atoms, aromatic and hydroaromatic radicals and at least two of the same are selected from the group consisting of aromatic and hydroaromatic radicals.
- liquid ester is an alkyl diester of a saturated aliphatic dicarboxylic acid.
- liquid diester is a branched chain alkyl diester of a saturated dicarboxylic acid.
- a fluid composition comprising a liquid branched chain alkyl diester of a saturated aliphatic dicarboxylic acid, which ester has a boiling point not lower than 150 C., a metal soap and a small amount of a tetraaryl orthosilicate.
- a grease composition comprising a liquid branched chain alkyl diseter of a dicarboxylic acid of the formula:
- R1 is a bivalent aliphatic hydrocarbon radical of from 3 to carbon atoms, which ester has a boiling point not lower than 150 C. and is thickened with a metal soap selected from the group consisting of alkaline earth and alkali metal soaps, and a small amount of a tetraaryl orthosilicate.
- a fluid composition comprising a liquid branched chain alkyl diester of a saturated aliphatic dicarboxylic acid, a metal soap and a small amount of a tetrahydroaryl orthosilicate.
- a grease composition comprising a liquid branched chain alkyl diester of a dicarboxylic acid of the formula:
- R4 is a bivalent aliphatic hydrocarbon radical of from 3 to 10 carbon atoms, which ester hasa boiling point not lower than C. and is thickened with a metal soap of the group consisting of alkaline earth and alkali metal soaps, and a small amount of a tetrahydroaryl orthosilicate.
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- Chemical & Material Sciences (AREA)
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Description
FLUID COMPOSITIONS CONTAINING AN ORTHOSILICATE Robert L..Merker, Bellevue, Pa., and William A. Zisman, Washington, D. C.
No Drawing. Application June 18, 1953, Serial No. 362,696
9 Claims. (Cl. 252-40.7)
(Granted under Title 35, U. S. Code (1952), sec. 266) This invention relates to new fluid compositions having lubricating properties, more particularly to improved aliphatic ester oils and greases.
The aliphatic ester oils to which reference is made herein and with which the present invention is concerned are liquid saturated aliphatic normal esters of saturated aliphatic carboxylic acids which esters are further defined by the fact that their boiling point is 150 C. or higher. This class of liquid aliphatic esters has been recognized by the art as a source of synthetic lubricating oils and some of these esters have been used with metal soaps for making greases. The art is also aware that metal soaps accelerate the thermal oxidation of these liquid aliphatic esters and has added antioxidants to the greases to improve their oxidation stability.
The present inventionas has an object the provision of a new class of antioxidants for improving the oxidation stability of the aliphatic ester oils which contain metal soaps, especially at elevated temperatures. A further object is the provision of aliphatic ester oil greases which have enhanced oxidation stability at elevated temperatures. Other objects will appear hereinafter from the description of the invention.
We have found that the oxidation stability at elevated temperatures of aliphatic ester oils which contain metal soaps can be improved by the addition thereto of small amounts of an orthosilicate which is aromatic or hydroaromatic or mixed aromatic-hydroaromatic in character. The orthosilicate antioxidants of the present invention contain an aromatic or hydroaromatic group on each of at least two of the ester oxygen atoms of the molecule, with a lower alkyl group being attached to such of the ester oxygen atoms as are not satisfied by an aromatic or hydroaromatic group. These orthosilicates have the general formula:
R-O O R2 S1 R1O/ ORa wherein R, R1, R2 and R3 each represent an aromatic or a hydroaromatic radical, or in part represent a lower alkyl radical of up to 6 carbon atoms where only two or three of the ester oxygen atoms of the orthosilicate molecule are attached to an aromatic or hydroaromatic radical. The radicals R, R1, R2 and R3 may be the same or different aromatic and hydroaromatic groups and the same or difierent lower alkyl groups where two such are present in the orthosilicate molecule. The radicals R, R1, R2 and R3 may be aryl or hydroaryl groups which may be substituted or not by groups such as, for example, alkyl, cycloalkyl, aralkyl, alkoxy, aryloxy, hydoxy, carboxy, carbalkoxy, nitro, amino, alkylamino, arylamino, etc., groups. Thus, the aromatic radical of the ortho-silicates may be, for example, phenyl, naphthyl, diphenyl, tolyl, xylyl, cyclohexylphenyl, benzylphenyl, anisyl, phenoxyphenyl, hydroxyphenyl, carboxyphenyl, carbethoxyphenyl, nitrophenyl, aminophenyl, N-methyli d States Patent 9 1 aromatic radical of the orthosilicates may be, for exby weight.
ample, cyclohexenyl, cyclohexyl, decalyl, tetralyl, methylcyclohexyl, dicyclohexyl, phenylcyclohexyl, benzylcyclohexyl, hexahydroanisyl, phenoxycyclohexyl, hydroxycyclohexyl, carboxycyclohexyl, carbethoxycyclohexyl, nitrocyclohexyl, aminocyclohexyl, N-methylaminocyclohexyl, N-phenylaminocyclohexyl, etc., groups. Where the group attached to the oxygen atom of the orthosilicate molecule is a lower alkyl radical the same may be, for example, methyl, ethyl, propyl, butyl, tertiary butyl, hexyl, etc. Illustrative orthosilicate compounds coming within the above general formula are, for example, tetraphenyl orthosilciate, tetra-o-tolyl orthosilicate, tetradiphenyl orthosilicate, tetra-B-naphthyl orthosilicate, tetracyclohexyl orthosilicate, di-methyl-di-phenyl orthosilicate, methyl-tri-phenyl orthosilicate and ethyl-tri-o-tolyl orthosilicate.
A preferred class of the orthosilicate compounds as antioxidants for the new fluid compositions are those in which the aromatic and hydroaromatic groups are attached to the ester oxygen atoms of the orthosilicate molecule are monoor dinuclear and more preferably are monoand dinuclear aryl and hydroaryl groups which may or may not contain lower alkyl groups, for example, methyl, ethyl, isopropyl, butyl, tertiary butyl, hexyl, etc., groups. Within this preferred group of orthosilicate compounds is to be mentioned in partciular, tetraphenyl orthosilicate and tetracyclohexyl orthosilicate.
The stability to oxidation, especially at elevated temperatures, e. g. at to C., of the aliphatic ester oil-metal soap compositions can be enhanced by the addition thereto of one of the antioxidant orthosilicates in concentrations within the range of about 0.1 and 10% by weight therein, with a preferred general range for the addition of the antioxidant being from about 0.1 to 5% The amount of the antioxidant added will depend upon the activity of the individual orthosilicates and the particular aliphatic ester oil-metal soap composition. The orthosilicate compound is dissolved or dispersed in the aliphatic ester oil depending upon its solubility therein.
The aliphatic ester oils of the compositions of the invention may be prepared by complete esterification in known way between the corresponding saturated aliphatic carboxylic acids, for example, butyric, oxalic, adipic, 3- methyladipic, azelaic, tricarballylic acids, etc., and the corresponding saturated aliphatic alcohols, for example, methanol, 2-ethylhexanol, ethyleneglycol, glycerol, pentaethrythritol, etc.; the acids and the alcohols being selected so as to obtain the desired liquid normal ester as will be understood by those skilled in the art. A class of esters of particular interest for the compositions of the present invention are the liquid saturated aliphatic diesters of the saturated aliphatic dicarboxylic acids which.
have an alkylene chain of 3 or more carbon atoms, more especially those which are straight or branched chain alkyl diesters of the 5 to 12 carbon atom alkylene dicarboxylic acids in which the alkylene chain may be branched or unbranched and which have the general formula:
ethylhexyl azelate, di-Z-ethylhexyl sebacate, di-(3,5,5
3 trimethylhexyl) sebacate, 2,4-pentanediol dihexanoate, triamyl tricarballylate, pentaethryritol tetrahexanoate, etc. The metal soap in the compositions of the invention may be any of the metal salts of the soap-forming fatty and hydroxy fatty acids, for example, the calcium, strontium, barium, sodium, potassium, lithium, copper, tin,
lead, zinc, aluminum, etc., salts of lauric, myristic,
palmitic, oleic, ricinoleic, stearic, arachidic, behenic, erucic, 12-hydroxy stearic acid, etc., or of mixtures of these acids. The amount of the metal soap in the compositions may be widely varied and range from as little as about 0.1% by weight up to a practical maximum. In the case of lubricating greases, the metal soap content of the compositions will generally be from about to 30% by weight, for which usually there is employed one of the alkaline earth or alkali metal soaps, for example, calcium, strontium, barium, sodium and lithium stearates.
The invention is illustrated in greater detail by the following specific examples in which the orthosilicate compound was incorporated in a lithium soap-diester grease and subjected to an accelerated oxidation test to determine its efiicacy as an antioxidant for the metal soap-diester oil composition at elevated temperatures. The greases were prepared in conventional manner by heating the aliphatic ester oil and metal soap together under stirring to form a clear solution, quickly cooling the solution to form a gel and working the gel through a screen to obtain a grease of uniform consistency (about workings through a Hain Microworker). The antioxidant was mixed into the grease and the whole then worked through the screen as before to obtain uniformity of admixture. The control grease or blank was made up to contain the same relative proportion of the metal soap and diester oil in each instance but without the presence of the orthosilicate anti-oxidant. The accelerated oxidation tests were carried out in accordance with Navy Specification ANG-3a(2) using a Norma-Holiman bomb apparatus.
Example 1 A grease was prepared to contain 16.2 mol percent (11.12% by weight) lithium stearate, 80.8 mol percent (87.68% by weight) di-Z-ethylhexyl sebacate and 3.0 mol percent (1.2% by weight) tetraphenyl orthosilicate. A control grease was made up in the same manner to contain only lithium stearate and di-Z-ethylhexyl sebacate in the same relative proportions.
Twenty gram samples of each of the two greases were placed in separate Norma-Hoffman bombs which were then sealed, heated to 100 C. and oxygen pressed thereinto at 110 pounds per square inch. The oxidation test was run for a period of 300 hours during which time the temperature in bombs was maintained at 100 C. L0.5 C.
Bomb pressure readings were made at intervals over the 300 hour period, which readings were accurate to :10 p. s. i. Consumption of oxygen by the grease and thereby oxidation of the same is indicated by drop in the oxygen pressure in the bomb. Readings of the pres sure in the bomb containing the control grease showed a rather sharp drop even in the earlier stages of the run (up to 50 hours) which was progressive until at the end of the 300 hours, the pressure stood at 50 pounds per square inch, indicating a substantial amount of oxidation to have taken place in the unprotected grease. On the other hand, pressure readings in the bomb containing the grease to which the tetraphenyl orthosilicate had been added showed no drop in pressure over the 300 hour period, indicating the orthosilicate compound to be a particularly effective antioxidant for the grease.
Example 2 The oxidation test of Example 1 was applied concurrently to a like grease containing 3 mol percent tetracyclohexyl orthosilicate in place of the tetraphenyl orthosilicate, using the same constant temperature bath to heat the bomb. Bomb pressure readings showed only a very small drop in pressure over the period of 300 hours, approximately 2 to 3 p. s. i., indicating the tetracyclohexyl orthosilicate to be also a particularly effective antioxidant for the grease.
Example 3 A grease was made up to contain 12% by weight lithium stearate, 3.2% by weight tetraphenyl orthosilicate and the remainder di-Z-ethylhexyl sebacate was subjected to the like oxidation test as in Example 1 but at a temperature of 150 C., and for a period of 20 hours. The grease containing the tetraphenyl orthosilicate showed an 8.0 p. s. i. drop in oxygen pressure after 20 hours whereas the control for the same period showed a drop of 57 p. s. i. oxygen pressure, indicating the orthosilicate compound to be an effective antioxidant for the grease at 150 C.
The aliphatic ester oil-metal soap compositions of the present invention maybe blended with miscible proportions of other lubricating oils, such as petroleum oils and polyoxyalkylene oxides having one or both terminals ending in an alkyl other group, e. g., the butoxy group. Antioxidants of types other than the orthosilicates may be used in the compositions in conjunction with the tetraaromatic and tetrahydroaromatic orthosilicate antioxidants, such as phenolic and aromatic amine type antioxidants which are active as antioxidants at the lower temperatures, e. g. below C., and thereby will impart supplemental protection to the aliphatic ester oilmetal soap compositions at temperatures occurring during storage or during other low temperature nonoperating periods, e. g., cyclohexyl phenol, p-hydroxy diphenyl, 4-t-butyl-Z-phenylphenol, thymol, catechol, phenyl-anapthylamine, etc. Other antioxidant compounds of the non-silicate type are dialkyl selenides, e. g., dilauryl selenide, and phenothiazine. Some of these supplemental antioxidant compounds are active, at the elevated temperatures also, for example, dilauryl selenide and phenothiazine.
While in the foregoing description we have made reference to certain specific embodiments of the invention, these are intended by way of illustration and not in limitation since the invention may be variously embodied without departing from the spirit or scope of the appended claims.
The invention described herein may be manufactured and used by or for the Government of the United States of America for governmental purposes without the payment of any royalties thereon or therefor.
What we claim is:
1. A fluid composition comprising a liquid saturated aliphatic normal ester of a saturated aliphatic carboxylic acid, which ester has a boiling point not lower than C., a metal. soap, and a small amount of an orthosilicate of the general formula:
wherein R, R1, R2 and Rs are selected from the group consisting of lower alkyl radicals having up to 6 carbon atoms, aromatic and hydroaromatic radicals and at least two of the same are selected from the group consisting of aromatic and hydroaromatic radicals.
2. A fluid composition as defined in claim 1, wherein the liquid ester is an alkyl diester of a saturated aliphatic dicarboxylic acid.
3. A fluid composition as defined in claim 1, wherein the liquid diester is a branched chain alkyl diester of a saturated dicarboxylic acid.
4. A fluid composition comprising a liquid branched chain alkyl diester of a saturated aliphatic dicarboxylic acid, which ester has a boiling point not lower than 150 C., a metal soap and a small amount of a tetraaryl orthosilicate.
5. A grease composition comprising a liquid branched chain alkyl diseter of a dicarboxylic acid of the formula:
wherein R1 is a bivalent aliphatic hydrocarbon radical of from 3 to carbon atoms, which ester has a boiling point not lower than 150 C. and is thickened with a metal soap selected from the group consisting of alkaline earth and alkali metal soaps, and a small amount of a tetraaryl orthosilicate.
6. A grease composition as defined in claim 5, wherein the tetraaryl orthosilicate is tetraphenyl orthosilicate.
7. A fluid composition comprising a liquid branched chain alkyl diester of a saturated aliphatic dicarboxylic acid, a metal soap and a small amount of a tetrahydroaryl orthosilicate.
8. A grease composition comprising a liquid branched chain alkyl diester of a dicarboxylic acid of the formula:
HOOCR4COQH wherein R4 is a bivalent aliphatic hydrocarbon radical of from 3 to 10 carbon atoms, which ester hasa boiling point not lower than C. and is thickened with a metal soap of the group consisting of alkaline earth and alkali metal soaps, and a small amount of a tetrahydroaryl orthosilicate.
9. A grease composition as defined in claim 8, wherein the tetrahydroaryl orthosilicate is tetracyclohexyl orthosilicate.
References Cited in the file of this patent UNITED STATES PATENTS 2,053,474 Graves et al. Sept. 8, 1936 2,129,281 Lincoln et al. Sept. 6, 1938 2,181,914 Rosen Dec. 5, 1939 2,242,400 Loane et al. May 20, 1941 2,335,012 Johnston Nov. 23, 1943 2,383,605 Lieber et al. Aug. 28, 1945 2,436,347 Zimmer et a1. Feb. 17, 1948 2,643,263 Morgan June 23, 1953 OTHER REFERENCES Fitzsimmons et al.: Polyorganosiloxanes, Orgonosilanes, and Orthosilicate Esters as Antioxidant, published by Naval Research Labororatories. Copy in Oifice of Technical Information.
Claims (1)
1. A FLUID COMPOSITION COMPRISING A LIQUID SATURARED ALIPHATIC NORMAL ESTER OF A SATURATED ALIPHATIC CARBOXYLIC ACID, WHICH ESTER HAS A BOILING POINT NOT LOWER THAN 150* C., A METAL SOAP, AND A SMALL AMOUNT OF AN ORTHOSILICATE OF THE GENERAL FORMULA:
Publications (1)
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US2735816A true US2735816A (en) | 1956-02-21 |
Family
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US2735816D Expired - Lifetime US2735816A (en) | Fluid compositions containing an |
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Cited By (3)
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US2964561A (en) * | 1956-07-26 | 1960-12-13 | Gen Aniline & Film Corp | Stabilization of aromatic amines |
US2990367A (en) * | 1954-06-21 | 1961-06-27 | Philipp Corp | Clay-bodied lubricant containing a silicate ester |
US3240622A (en) * | 1962-08-27 | 1966-03-15 | Du Pont | Lubricating elastomers with silicate esters |
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US2053474A (en) * | 1934-12-11 | 1936-09-08 | Du Pont | Higher alkyl borates and silicates and process for preparing same |
US2129281A (en) * | 1936-03-23 | 1938-09-06 | Continental Oil Co | Lubricating oils |
US2181914A (en) * | 1935-03-19 | 1939-12-05 | Standard Oil Dev Co | Oil composition containing arylated metallo-organic inhibitors |
US2242400A (en) * | 1937-09-13 | 1941-05-20 | Standard Oil Co | Extreme pressure lubricant |
US2335012A (en) * | 1941-04-12 | 1943-11-23 | Little Inc A | High boiling compounds and method of preparing them |
US2383605A (en) * | 1942-12-31 | 1945-08-28 | Standard Catalytic Co | Lubricants and preparation thereof |
US2436347A (en) * | 1944-12-30 | 1948-02-17 | Standard Oil Dev Co | Grease compositions |
US2643263A (en) * | 1950-09-22 | 1953-06-23 | California Research Corp | Higher secondary-alkyl orthosilicates |
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0
- US US2735816D patent/US2735816A/en not_active Expired - Lifetime
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US2053474A (en) * | 1934-12-11 | 1936-09-08 | Du Pont | Higher alkyl borates and silicates and process for preparing same |
US2181914A (en) * | 1935-03-19 | 1939-12-05 | Standard Oil Dev Co | Oil composition containing arylated metallo-organic inhibitors |
US2129281A (en) * | 1936-03-23 | 1938-09-06 | Continental Oil Co | Lubricating oils |
US2242400A (en) * | 1937-09-13 | 1941-05-20 | Standard Oil Co | Extreme pressure lubricant |
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US2383605A (en) * | 1942-12-31 | 1945-08-28 | Standard Catalytic Co | Lubricants and preparation thereof |
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US2990367A (en) * | 1954-06-21 | 1961-06-27 | Philipp Corp | Clay-bodied lubricant containing a silicate ester |
US2964561A (en) * | 1956-07-26 | 1960-12-13 | Gen Aniline & Film Corp | Stabilization of aromatic amines |
US3240622A (en) * | 1962-08-27 | 1966-03-15 | Du Pont | Lubricating elastomers with silicate esters |
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