US3530070A - Synthetic lubricants - Google Patents
Synthetic lubricants Download PDFInfo
- Publication number
- US3530070A US3530070A US659332A US3530070DA US3530070A US 3530070 A US3530070 A US 3530070A US 659332 A US659332 A US 659332A US 3530070D A US3530070D A US 3530070DA US 3530070 A US3530070 A US 3530070A
- Authority
- US
- United States
- Prior art keywords
- polyol
- acids
- viscosity
- lubricant
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000314 lubricant Substances 0.000 title description 29
- 239000000203 mixture Substances 0.000 description 33
- 239000002253 acid Substances 0.000 description 26
- 229920005862 polyol Polymers 0.000 description 19
- 150000003077 polyols Chemical class 0.000 description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- 150000007513 acids Chemical class 0.000 description 13
- 229920005628 alkoxylated polyol Polymers 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 125000002947 alkylene group Chemical group 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 7
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 229940113165 trimethylolpropane Drugs 0.000 description 7
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000001050 lubricating effect Effects 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- -1 aliphatic polyol Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000010687 lubricating oil Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 238000010008 shearing Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 229940117969 neopentyl glycol Drugs 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- PDEDQSAFHNADLV-UHFFFAOYSA-M potassium;disodium;dinitrate;nitrite Chemical compound [Na+].[Na+].[K+].[O-]N=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PDEDQSAFHNADLV-UHFFFAOYSA-M 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 231100000241 scar Toxicity 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- 239000004243 E-number Substances 0.000 description 1
- 235000019227 E-number Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- RWCOTTLHDJWHRS-YUMQZZPRSA-N Pro-Pro Chemical compound OC(=O)[C@@H]1CCCN1C(=O)[C@H]1NCCC1 RWCOTTLHDJWHRS-YUMQZZPRSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001278 adipic acid derivatives Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001535 azelaic acid derivatives Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000010688 mineral lubricating oil Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920000196 poly(lauryl methacrylate) Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 108010077112 prolyl-proline Proteins 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003329 sebacic acid derivatives Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/108—Residual fractions, e.g. bright stocks
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
-
- 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
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/08—Resistance to extreme temperature
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/02—Bearings
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
- C10N2040/13—Aircraft turbines
-
- 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
- C10N2050/015—Dispersions of solid lubricants
- C10N2050/02—Dispersions of solid lubricants dissolved or suspended in a carrier which subsequently evaporates to leave a lubricant coating
-
- 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
- the invention is lubricant compositions which have as base compounds which may be made by esterifying with a mixture of acids the product of reaction of an alkylene oxide with a polyol.
- the compounds are found to have high viscosity indices and good resistance to shear stresses, and are therefore suitable for use in transmissions, gear boxes and the like.
- the present invention relates to synthetic lubricant compositions.
- Synthetic lubricant compositions based on adipic, sebacic or azelaic acid derivatives are known. These compositions are generally of low viscosity, i.e. of the order of 3 to 7 centistokes at 210 F. and find application as lubricants in jet engines where high temperatures and high journal speeds require the use of specialised lubricating compositions.
- the lubricant bases of the present invention have high viscosity indices, of the order of 140. This compares very favourably with the viscosity index of mineral oils which are used as lubricant bases and have viscosity indices up to about 90.
- the viscosity index of the mineral oil can be improved by adding compounds such as polylauryl methacrylate.
- the viscosity index improver breaks down, and the viscosity index of the lubricant tends to revert to the viscosity index of the base.
- lubricants which rely on additives to improve the viscosity index must be replaced at fairly frequent intervals, whereas lubricant compositions comprising the lubricant base of our invention do not suffer from this drawback.
- the present invention is a synthetic lubricant composition wherein the lubricant base comprises a mixed ester of an alkoxylated polyol (as hereinafter defined) with at least two carboxylic acids, wherein the acids each contain from 3 to 15 carbon atoms.
- alkoxylated polyol a compound which may be made by reaction of a polyol with an alkylene oxide having at least three carbon atoms. This is the preferred method for producing the alkoxylated polyol, but the invention is not confined to the use of compounds made in this particular manner.
- Suitable polyols are trimethylol propane, glycerol, pentaerythritol, dipentaerythritol, sorbitol and neopentylglycol.
- a preferred polyglycol is trimethylolpropane.
- the preferred alkylene oxide is propylene oxide, although it is possible to use mixtures of two or more different alkylene oxides for reaction with the polyol.
- the alkoxylated polyol may contain from 1 to 24, preferably 1 to 6 substituent alkoxy groups per hydroxyl group of the polyol.
- the preferred carboxylic acids are aliphatic monobasic acids.
- Suitable acids may include high molecular weight acids such as heptoic, caprylic, pelargonic, capric and lauric acid and lower molecular weight acids such as propionic, butyric and valeric acid. It is preferred to use mixtures of lower and higher molecular weight acid for esterifying the alkoxylated polyol. By using mixtures of acids it is possible to exercise finer control over the viscosity of the final product.
- the lubricant bases of the present invention may be prepared in any convenient manner.
- the polyol may be reacted with the desired alkylene oxide or mixtures of oxides, the reaction being carried out under pressure in an autoclave and preferably in the presence of a suitable alkaline catalyst e.g. caustic soda or sodium methoxide.
- a suitable alkaline catalyst e.g. caustic soda or sodium methoxide.
- the autoclave mixture is neutralised with acid, e.g. benzene sulphonic acid, an excess of acid added and the mixture esterified with the fatty acids.
- the esterification may be carried out in any convenient manner.
- the alkoxylated polyol may be esterified in a single step by reaction with a mixture of the higher and lower molecular weight fatty acids.
- the alkoxylated polyol is first partially esterified with a higher molecular weight acid or acids and the esterification completed by esterification with lower molecular weight acid or acids. It is desirable that the final product contains no hydroxyl groups, so the alkoxylated polyol is reacted with the higher acid and then subsequently with the more reactive lower acid to esterify all the remaining hydroxyl groups.
- the lubricant base should be miscible with other base fluids for example the mineral oils commercially available as Pool 12 and Brightstock.
- mineral oils commercially available as Pool 12 and Brightstock.
- the ratio of carbon atoms to oxygen atoms is greater than 3.4:1.
- Compounds in which the ratio is greater than 3.921 are particularly preferred.
- the synthetic lubricant compositions of the present invention show high performance and high temperature stability and have lubricating properties corresponding to those of a mineral lubricating oil.
- the compositions may comprise other conventional oil additives, e.g. antisludge agents, extreme pressure agents and antioxidants known in the art.
- compositions of the present invention are illustrated by the following examples:
- a synthetic lubricant composition having a lubricant base which comprises a mixed ester of an oxypropylated polyol, which polyol contains only hydroxyl groups in addition to carbon and hydrogen, said oxypropylated polyol being obtained by reaction of propylene oxide with an aliphatic polyol and said ester being of liquid lubricating oil viscosity and having no free hydroxyl groups and the acids used to form the ester being a mixture of higher molecular Weight acids selected from heptoic, caprylic, pelargonic, capric and lauric acids and lower molecular weight acids selected from propionic, butyric and valeric acids, the higher and lower molecular weight acids being present in amounts sufiicient to adjust the viscosity of the lubricant composition.
- composition according to claim 1 wherein the ratio of carbon atoms to oxygen atoms in the base is greater than 3.4: 1.
- composition according to claim 1 wherein the polyol is trimethylol propane, glycerol, pentaerythritol, dipentaerythritol, sorbitol or neopentylglycol.
- composition according to claim 1 wherein the oxypropylated aliphatic polyol contains from 1 to 24 substituent oxypropyl groups per hydroxyl group of the polyol.
- composition according to claim 1 wherein the lubricant base has a high viscosity index of the order of and has incorporated therein an additive selected from the group consisting of antisludge agents, antioxidants and extreme pressure agents.
- a synthetic lubricant composition made up of a liquid lubricant base of lubricating oil viscosity and an additive wherein the lubricant base comprises a major proportion of an ester of an oxypropylated aliphatic polyol, obtained by reaction of propylene oxide with trimethylolpropane, with a mixture of carboxylic acids wherein one component of the mixture is selected from the group consisting of heptoic, caprylic, pelargonic, capric and lauric acids, and the other component is selected from the group consisting of propionic, butyric and valeric acids, each acid component being present in amounts sufficient to adjust the viscosity of the lubricant composition.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB28547/66A GB1135095A (en) | 1966-06-24 | 1966-06-24 | Improvements in or relating to drinking valves for poultry |
| GB37886/66A GB1157653A (en) | 1966-06-24 | 1966-08-24 | Improvements in or relating to Synthetic Lubricants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3530070A true US3530070A (en) | 1970-09-22 |
Family
ID=26259438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US659332A Expired - Lifetime US3530070A (en) | 1966-06-24 | 1967-08-09 | Synthetic lubricants |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3530070A (de) |
| AT (2) | AT278222B (de) |
| BE (3) | BE700186A (de) |
| CH (1) | CH451590A (de) |
| DE (2) | DE1644863A1 (de) |
| GB (2) | GB1157753A (de) |
| NL (3) | NL6708828A (de) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4031118A (en) * | 1973-09-17 | 1977-06-21 | The Lubrizol Corporation | Ester-containing process and compositions |
| WO2012134792A1 (en) * | 2011-03-29 | 2012-10-04 | Dow Global Technologies Llc | Lubricant composition |
| WO2019126923A1 (en) | 2017-12-25 | 2019-07-04 | Dow Global Technologies Llc | Modified oil soluble polyalkylene glycols |
| WO2019236446A1 (en) | 2018-06-04 | 2019-12-12 | Tetramer Technologies, Llc | Lubricating base oils from esterified alkoxylated polyols using saturated long-chain fatty acids |
| WO2022125081A1 (en) | 2020-12-09 | 2022-06-16 | Tetramer Technologies, Llc | Biodegradable lubricant with tailored hydrolytic stability and improved thermal stability through alkoxylation of glycerol |
| EP4010384A4 (de) * | 2019-08-08 | 2023-01-25 | Dow Global Technologies, LLC | Esterifizierte öllösliche polyalkylenglykole |
| US11680218B2 (en) | 2018-06-04 | 2023-06-20 | Tetramer Technologies, Llc | Biodegradable lubricant with tailored hydrolytic stability and improved thermal stability through alkoxylation of glycerol |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2024051C3 (de) * | 1970-05-16 | 1986-05-07 | Henkel KGaA, 4000 Düsseldorf | Verwendung der Veresterungsprodukte von Glycerin-Äthylenoxid-Addukten mit Fettsäuren als Rückfettungsmittel in kosmetischen Zubereitungen |
| US5266346A (en) * | 1989-02-16 | 1993-11-30 | Nabisco, Inc. | Extended ester derivatives as low calorie fat mimetics |
| AU6869996A (en) * | 1995-09-13 | 1997-04-01 | Morten Sloth Weidner | Use of esters of polyhydric alcohols to enhance the oral bioavailability of drug substances as well as novel esters and pharmaceutical compositions containing them |
| DE10211801B4 (de) * | 2002-03-16 | 2004-09-30 | Clariant Gmbh | Kosmetische und pharmazeutische Zubereitungen enthaltend einen oxalkylierten Polyglycerinester |
| AU2010321882B2 (en) * | 2009-11-18 | 2016-01-14 | Nektar Therapeutics | Salt form of a multi-arm polymer-drug conjugate |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2457139A (en) * | 1946-02-26 | 1948-12-28 | Carbide & Carbon Chem Corp | Esters of polyoxyalkylene diols |
| US2514982A (en) * | 1946-10-18 | 1950-07-11 | Shell Dev | Stabilized lubricant |
| US2604453A (en) * | 1948-12-30 | 1952-07-22 | Standard Oil Dev Co | New copolymer compositions |
| US2665312A (en) * | 1951-08-03 | 1954-01-05 | Dow Chemical Co | Stabilized polyglycol compositions |
| US3062671A (en) * | 1962-11-06 | Hard ester waxes and process for | ||
| US3137737A (en) * | 1959-09-04 | 1964-06-16 | Standard Oil Co | Telomerization of unsaturated hydrocarbons with polyoxyalkylene compounds and telomeric products and synthetic lubricants obtained thereby |
| US3337595A (en) * | 1960-09-15 | 1967-08-22 | Nalco Chemical Co | Fatty acid esters of polyoxypropylated glycerol |
-
1966
- 1966-08-24 GB GB28547/67A patent/GB1157753A/en not_active Expired
- 1966-08-24 GB GB37886/66A patent/GB1157653A/en not_active Expired
-
1967
- 1967-06-19 BE BE700186D patent/BE700186A/xx unknown
- 1967-06-23 NL NL6708828A patent/NL6708828A/xx unknown
- 1967-06-23 CH CH891067A patent/CH451590A/de unknown
- 1967-08-09 US US659332A patent/US3530070A/en not_active Expired - Lifetime
- 1967-08-12 DE DE19671644863 patent/DE1644863A1/de active Pending
- 1967-08-21 AT AT768767A patent/AT278222B/de not_active IP Right Cessation
- 1967-08-21 AT AT768867A patent/AT281250B/de not_active IP Right Cessation
- 1967-08-22 DE DE19671644864 patent/DE1644864A1/de active Pending
- 1967-08-23 NL NL6711608A patent/NL6711608A/xx unknown
- 1967-08-23 NL NL6711607A patent/NL6711607A/xx unknown
- 1967-08-24 BE BE703052D patent/BE703052A/xx unknown
- 1967-08-24 BE BE703051D patent/BE703051A/xx unknown
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3062671A (en) * | 1962-11-06 | Hard ester waxes and process for | ||
| US2457139A (en) * | 1946-02-26 | 1948-12-28 | Carbide & Carbon Chem Corp | Esters of polyoxyalkylene diols |
| US2514982A (en) * | 1946-10-18 | 1950-07-11 | Shell Dev | Stabilized lubricant |
| US2604453A (en) * | 1948-12-30 | 1952-07-22 | Standard Oil Dev Co | New copolymer compositions |
| US2665312A (en) * | 1951-08-03 | 1954-01-05 | Dow Chemical Co | Stabilized polyglycol compositions |
| US3137737A (en) * | 1959-09-04 | 1964-06-16 | Standard Oil Co | Telomerization of unsaturated hydrocarbons with polyoxyalkylene compounds and telomeric products and synthetic lubricants obtained thereby |
| US3337595A (en) * | 1960-09-15 | 1967-08-22 | Nalco Chemical Co | Fatty acid esters of polyoxypropylated glycerol |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4031118A (en) * | 1973-09-17 | 1977-06-21 | The Lubrizol Corporation | Ester-containing process and compositions |
| WO2012134792A1 (en) * | 2011-03-29 | 2012-10-04 | Dow Global Technologies Llc | Lubricant composition |
| US20140011723A1 (en) * | 2011-03-29 | 2014-01-09 | Dow Global Technologies Llc | Lubricant composition |
| WO2019126923A1 (en) | 2017-12-25 | 2019-07-04 | Dow Global Technologies Llc | Modified oil soluble polyalkylene glycols |
| EP3732228A4 (de) * | 2017-12-25 | 2021-08-18 | Dow Global Technologies LLC | Modifizierte öllösliche polyalkylenglykole |
| US11279897B2 (en) | 2017-12-25 | 2022-03-22 | Dow Global Technologies Llc | Modified oil soluble polyalkylene glycols |
| WO2019236446A1 (en) | 2018-06-04 | 2019-12-12 | Tetramer Technologies, Llc | Lubricating base oils from esterified alkoxylated polyols using saturated long-chain fatty acids |
| US11230682B2 (en) | 2018-06-04 | 2022-01-25 | Tetramer Technologies, Llc | Lubricating base oils from esterified alkoxylated polyols using saturated long-chain fatty acids |
| US11680218B2 (en) | 2018-06-04 | 2023-06-20 | Tetramer Technologies, Llc | Biodegradable lubricant with tailored hydrolytic stability and improved thermal stability through alkoxylation of glycerol |
| US11807826B2 (en) | 2018-06-04 | 2023-11-07 | Universtiy of South Carolina | Lubricating base oils from esterified alkoxylated polyols using saturated long-chain fatty acids |
| EP4010384A4 (de) * | 2019-08-08 | 2023-01-25 | Dow Global Technologies, LLC | Esterifizierte öllösliche polyalkylenglykole |
| WO2022125081A1 (en) | 2020-12-09 | 2022-06-16 | Tetramer Technologies, Llc | Biodegradable lubricant with tailored hydrolytic stability and improved thermal stability through alkoxylation of glycerol |
Also Published As
| Publication number | Publication date |
|---|---|
| AT281250B (de) | 1970-05-11 |
| BE703051A (de) | 1968-02-26 |
| NL6711607A (de) | 1968-02-26 |
| NL6711608A (de) | 1968-02-26 |
| AT278222B (de) | 1970-01-26 |
| GB1157753A (en) | 1969-07-09 |
| CH451590A (de) | 1968-05-15 |
| DE1644863A1 (de) | 1970-12-03 |
| BE700186A (de) | 1967-12-01 |
| DE1644864A1 (de) | 1970-12-03 |
| GB1157653A (en) | 1969-07-09 |
| BE703052A (de) | 1968-02-26 |
| NL6708828A (de) | 1967-12-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3562300A (en) | Liquid neoalkylpolyol esters of mixtures of neo-and straight or branched chain alkanoic acids and their preparation | |
| US3530070A (en) | Synthetic lubricants | |
| US4826633A (en) | Synthetic lubricant base stock of monopentaerythritol and trimethylolpropane esters | |
| US4362635A (en) | Lactone-modified ester oils | |
| US3694382A (en) | Ester lubricant | |
| US3778454A (en) | Complex ester | |
| US3309318A (en) | Blends of ester lubricants | |
| US3202701A (en) | Complex ester of mixed dicarboxylic acids, neopentyl glycol and aliphatic alcohols | |
| US3773668A (en) | Lubricating compositions | |
| US2599803A (en) | Lubricating composition | |
| US2994662A (en) | Lubricating compositions | |
| US3281359A (en) | Neopentyl polyol derivatives and lubricating compositions | |
| US20040209788A1 (en) | Synthetic lubricant base stock formed from high content branched chain acid mixtures | |
| US4243540A (en) | Organic esters for lubricating compositions | |
| EP0518567B1 (de) | Aus mit einem hohen Gehalt an verzweigtkettigen Säuremischungen hergestellte synthetische Grundschmieröle | |
| US3720695A (en) | Water soluble lubricant | |
| US3634245A (en) | Water soluble lubricant | |
| US4313890A (en) | Polyol ester functional fluids | |
| US3134737A (en) | Novel titanium compound and lubricating composition containing said compound | |
| US3304261A (en) | Mineral lubricating oil compositions containing terpolymer viscosity index improvers | |
| JPS6057480B2 (ja) | ネオペンチルポリオ−ルエステルを基油とする内燃機関用潤滑剤 | |
| EP1051465A1 (de) | Verwendung biologisch abbaubarer olsäure-estolid-ester als basisöl und schmieröl | |
| US3560387A (en) | Lubricating oils | |
| US3206401A (en) | Lubricating oil compositions containing ester of mercapto acid and a phosphonate | |
| US3472775A (en) | Synthetic ester lubricant base fluid containing a polyester thickener |