EP1981955B9 - Improved high temperature lubricant compositions - Google Patents
Improved high temperature lubricant compositions Download PDFInfo
- Publication number
- EP1981955B9 EP1981955B9 EP07762776.8A EP07762776A EP1981955B9 EP 1981955 B9 EP1981955 B9 EP 1981955B9 EP 07762776 A EP07762776 A EP 07762776A EP 1981955 B9 EP1981955 B9 EP 1981955B9
- Authority
- EP
- European Patent Office
- Prior art keywords
- lubricant composition
- lubricant
- weight
- base oil
- percent
- 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.)
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- 239000000314 lubricant Substances 0.000 title claims description 103
- 239000000203 mixture Substances 0.000 title claims description 101
- 229920005862 polyol Polymers 0.000 claims description 59
- 239000002199 base oil Substances 0.000 claims description 54
- -1 neopentyl polyol Chemical class 0.000 claims description 42
- 239000007795 chemical reaction product Substances 0.000 claims description 41
- 239000000654 additive Substances 0.000 claims description 40
- 150000002148 esters Chemical class 0.000 claims description 34
- 230000000996 additive effect Effects 0.000 claims description 26
- 229920000728 polyester Polymers 0.000 claims description 26
- 229910052751 metal Inorganic materials 0.000 claims description 24
- 239000002184 metal Substances 0.000 claims description 24
- 150000003077 polyols Chemical class 0.000 claims description 19
- QBTIHZIVENIGSW-UHFFFAOYSA-N 2-(4,4-dimethylpentan-2-yl)-5,7,7-trimethyloctanoic acid Chemical compound CC(C)(C)CC(C)CCC(C(O)=O)C(C)CC(C)(C)C QBTIHZIVENIGSW-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000003118 aryl group Chemical class 0.000 claims description 10
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 8
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229940059574 pentaerithrityl Drugs 0.000 claims description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- 230000001050 lubricating effect Effects 0.000 claims description 4
- 235000021317 phosphate Nutrition 0.000 claims description 4
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 4
- IKXFIBBKEARMLL-UHFFFAOYSA-N triphenoxy(sulfanylidene)-$l^{5}-phosphane Chemical class C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=S)OC1=CC=CC=C1 IKXFIBBKEARMLL-UHFFFAOYSA-N 0.000 claims description 4
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical compound CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 claims description 3
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 claims description 3
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 claims description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- NIMCSFUFFFUJQM-UHFFFAOYSA-N n-phenyl-2-(2,4,4-trimethylpentan-2-yl)naphthalen-1-amine Chemical compound CC(C)(C)CC(C)(C)C1=CC=C2C=CC=CC2=C1NC1=CC=CC=C1 NIMCSFUFFFUJQM-UHFFFAOYSA-N 0.000 claims description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 3
- PXZZRISEDBDRLY-UHFFFAOYSA-N (2-tert-butylphenyl) dihydrogen phosphate Chemical class CC(C)(C)C1=CC=CC=C1OP(O)(O)=O PXZZRISEDBDRLY-UHFFFAOYSA-N 0.000 claims description 2
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 claims description 2
- CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2h-benzotriazole Chemical compound CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 claims description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 claims description 2
- 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 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 2
- 239000012964 benzotriazole Substances 0.000 claims description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 claims description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 2
- HUDSKKNIXMSHSZ-UHFFFAOYSA-N dihexyl hydrogen phosphate Chemical class CCCCCCOP(O)(=O)OCCCCCC HUDSKKNIXMSHSZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002790 naphthalenes Chemical class 0.000 claims description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 2
- 240000007175 Datura inoxia Species 0.000 claims 1
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 14
- 230000000007 visual effect Effects 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 12
- 230000003647 oxidation Effects 0.000 description 12
- 238000007254 oxidation reaction Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000012530 fluid Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 230000001590 oxidative effect Effects 0.000 description 9
- 238000005461 lubrication Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 230000015556 catabolic process Effects 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 229920013639 polyalphaolefin Polymers 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000010504 bond cleavage reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 1
- XZOYHFBNQHPJRQ-UHFFFAOYSA-N 7-methyloctanoic acid Chemical compound CC(C)CCCCCC(O)=O XZOYHFBNQHPJRQ-UHFFFAOYSA-N 0.000 description 1
- VCIMZVUJVMTQMG-UHFFFAOYSA-N 7-methyloctanoic acid 3,5,5-trimethylhexanoic acid Chemical compound CC(C)CCCCCC(O)=O.OC(=O)CC(C)CC(C)(C)C VCIMZVUJVMTQMG-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010073310 Occupational exposures Diseases 0.000 description 1
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- PLSFNSJUKGEOSL-UHFFFAOYSA-N dioctoxy(oxo)phosphanium Chemical compound CCCCCCCCO[P+](=O)OCCCCCCCC PLSFNSJUKGEOSL-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010505 homolytic fission reaction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000010338 mechanical breakdown Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 231100000675 occupational exposure Toxicity 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000010701 perfluoropolyalkylether Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920002627 poly(phosphazenes) Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Chemical class 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 239000005076 polymer ester Substances 0.000 description 1
- 229920001296 polysiloxane Chemical class 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000012855 volatile organic compound Substances 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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/38—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
- C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
- C10M111/04—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a macromolecular organic compound
-
- 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
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
-
- 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
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
-
- 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
- C10M2203/106—Naphthenic fractions
- C10M2203/1065—Naphthenic fractions used as base material
-
- 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
- C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
-
- 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
- C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
- C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/022—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—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
- C10M2207/126—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 monocarboxylic
-
- 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
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
- C10M2207/2835—Esters of polyhydroxy compounds used as base material
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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
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/02—Viscosity; Viscosity index
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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
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/071—Branched chain compounds
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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
- 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
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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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
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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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/74—Noack Volatility
Definitions
- Lubricants that can maintain their structure under extremes of temperature are useful and essential in many commercial, domestic, and industrial applications. Such applications include, but are not limited to, fiberglass production, wood laminating, wood pressing, paint curing, textile production, and food baking. Lubricants can also be used in aerospace applications in which fluids are exposed to temperatures typically exceeding 200°C. Such high temperature lubrication fluids must also provide sufficient lubrication of metal surfaces to prevent wear, reduce friction, reduce energy consumption, and more importantly, prevent failure of mechanical systems.
- Lubricants that are used at high temperatures must also be resistant to thermal and/or oxidative breakdown and polymerization.
- Thermal and/or oxidative breakdown leads to the scission of lubricant molecules, which in turn, leads to the formation of lower molecular weight compounds that can be volatilized, depending upon the operational conditions of a mechanical system. This process normally results in an increased lubricant viscosity.
- an increase in lubricant viscosity reduces the mobility of the lubricant liquid, accelerates oxidation, and leads to the formation of deposits.
- Such breakdown may also result in loss of lubricant fluid and/or the production of excessive vapors and/or smoke, or ineffective lubrication.
- Liquid lubricant compositions typically have a base oil to which other additives are provided.
- the additives impart specific properties to the overall lubricant mixture.
- One class of such additives is metal protecting additives. These exhibit beneficial properties such as resistance to wear, protection from damage at extreme pressure, and resistance to corrosion. Such additives are also useful for protecting metal surfaces.
- One drawback of metal protecting additives, however, is that they can reduce stability of the base oils once added.
- lubricant protecting additives can be provided to the base oils.
- Lubricant protecting additives are helpful for maintaining a lubricant's structure under operational conditions.
- the most important lubricant protecting additives are antioxidants.
- Antioxidants protect a base oil in a lubricant composition and/or other additives therein from attack by atmospheric oxygen, a harmful process also known as oxidation, which produces unwanted free radicals and leads to instability.
- Antioxidants help to stabilize base oils by helping to prevent oxidation.
- the effectiveness of antioxidants is strongly influenced by the level of stability of the base oil or oils in the composition. Greater stability of the base oil helps to reduce potentially adverse effects of oxidation.
- a few types of compounds are mutinely used as liquid base oils in the field of high temperature lubricants, include perfluoropolyalkyl ethers which are highly resistant to oxidation due to the complete absence of extractable hydrogen atoms.
- Polyphenylethers and alkyldiphenyl ethers are also inherently very stable.
- their lubrication properties are poorer than other classes of base oils, and they tend to be either incompatible and/or not positively responsive to metal and/or lubricant protecting additives.
- due to the sophisticated synthesis techniques and manufacturing processes required to produce these materials they are only produced in small quantities unsuitable for large-scale industrial use.
- Synthetic esters are derived from the reaction of carboxylic acids and alcohols. Carboxylic acids and alcohols can be synthesized to very high purity, and thus, synthetic esters can be designed with very defined structures that can be targeted to provide the specific properties sought in a particular application. Synthetic esters are generally both compatible with, and respond favorably to common metal and lubricant protecting additives.
- Esters of certain carboxylic acids and alcohols are known to possess enhanced resistance to thermal and/or oxidative breakdown.
- Two general classes of commonly used synthetic esters with one or more of these properties are aromatic esters and neopolyol esters.
- Aromatic esters are formed as a reaction product of aromatic polycarboxylic acids, such as trimellitic acid and pyromellitic acid, and linear and/or branched monofunctional alcohols. Such alcohols typically have a carbon chain length of about 8 to about 13 carbon atoms.
- aromatic esters are prone to oxidationdue to the aromatic portion of the molecule, they can be useful due to their relatively high molecular weight and structural purity that contributes to a lower volatility.
- U.S. Patent No. 6,465,400 discloses a lubricant composition prepared by mixing aromatic esters with an additional base oil and antioxidants.
- Neopolyol esters are formed from the reaction of neopentyl polyols, such as neopentyl glycol, trimethylolpropane, pentaerythritol, and dipentaerythritol with linear and/or branched carboxylic acids that are typically about two to about ten carbon atoms in chain length.
- Neopolyol esters as a class are generally more resistant to oxidation than aromatic esters. They are particularly useful due to their higher thermal and oxidative stability which stems from the absence of hydrogens attached to carbons that are ⁇ to the ester linkage, which can lead to a low energy oxidation pathway.
- the carboxylic acids used to form such esters typically are linear and/or branched chain acids having from about five to about ten carbon atoms.
- U.S. Patent No. 4,826,633 discloses esters formed by reacting trimethylolpropane and monopentaerythritol with a mixture of linear and branched carboxylic acids having from 5 to 10 carbon atoms.
- U.S: Patent No. 6,436,981 discloses a high temperature lubricant formulation formed by reacting mainly dipentaerythritol with a mixture of linear and branched carboxylic acids having from 5 to 12 carbon atoms, that also includes a viscosity index improver.
- 6,884,861 discloses a high temperature lubricant composition including esters formed from the reaction of certain polyols with mixtures of carboxylic acids having a five to ten carbon chain length and/or aromatic acids.
- US4477383 discloses neopentyl polyol ester of isostearic acid as Lubricant base stock.
- Neopentyl polyol polyesters that are formed from certain relatively short chain linear or branched carboxylic acids of about 5 to about 10 carbons are particularly resistant to thermal and/or oxidative breakdown and/or polymerization relative to neopentyl polyol polyesters derived from longer chain carboxylic acids of about 12 carbons and longer.
- shorter chain carboxylic acids employed for forming neopentyl polyol polyester for use as base oils in lubricant compositions are pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, 2-ethylhexanoic acid, nonanoic acid, 3,5,5-trimethylhexanoic acid (isononanoic acid) and decanoic acid.
- the shorter chain carboxylic acids are preferred due to the shielding effect provided by the ester linkage that makes the hydrogen atoms on the carboxylic acid portion more resistant to abstraction and resultant oxidative attack.
- Longer chain carboxylic acids generally possess hydrogen atoms further away from the ester linkage that do not benefit from increased stability provided from the shielding effect of the ester linkage.
- the resulting molecular weight of the ester is typically limited, which can lead to higher volatility.
- Isononanoic acid is particularly resistant to oxidation due to the reduced presence of secondary hydrogen atoms and the steric crowding about the lone tertiary hydrogen atom.
- the resulting esters due to its highly branched nature, the resulting esters generally have higher volatility. Higher volatility of the base ester, and resulting oxidative scission products can lead to oil thickening that accelerates the formation of deposits, especially in thin films.
- the present invention includes a lubricant composition that has at least one polyol polyester.
- the polyol polyester is the reaction product of at least one neopentyl polyol and 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid which reaction product is present in the lubricant composition in an amount of from 0.5 to 99.5% by weight of the lubricant composition based on the total weight of the lubricant composition.
- the reaction product is a base oil in a lubricant composition.
- the lubricant composition including the reaction product as a base oil comprises at least one additional base oil.
- the lubricant composition including the reaction product as a base oil and comprising at least one additional base oil further comprises a lubricant protecting additive and/or a metal protecting additive.
- One embodiment of the present invention includes providing a lubricant composition that has at least one polyol polyester.
- the polyol polyester is the reaction product of a neopentyl polyol and 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid.
- the reaction product is a base oil in the composition, and the composition also has at least one additional base oil.
- the invention also includes a lubricant composition that has at least one polyol polyester.
- the polyol polyester is the reaction product of a neopentyl polyol and 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid.
- the reaction product is a base oil in the composition, and the composition further also has at least one additional base oil, at least one metal protecting additive, and/or at least one lubricant protecting additive.
- the method comprises applying a lubricant composition to a metal surface, wherein the lubricant composition comprises a) a reaction product of at least one neopentyl polyol and 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid wherein the reaction product is a base oil in the composition, b) at least one additional base oil, c) from about 0.5 to about 15 percent by weight of at least one lubricant protecting additive, and d) from about 0.1 to about 10 percent by weight of at least one metal protecting additive.
- the lubricant composition comprises a) a reaction product of at least one neopentyl polyol and 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid wherein the reaction product is a base oil in the composition, b) at least one additional base oil, c) from about 0.5 to about 15 percent by weight of at least one lubricant protecting additive, and
- a method of making a lubricant composition comprises reacting a) at least one neopentyl polyol and b) 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid wherein the reaction product is a base oil in the composition.
- the method may further comprise providing at least one additional base oil.
- the base oil can be present in an amount of from 5 to about 50 percent by weight of the lubricant composition and the additional base oil is present from about 50 to 90 percent of the lubricant composition.
- the method may further comprise providing from about 0.5 to about 15 percent by weight based on a weight of the lubricant composition of at least one lubricant protective additive.
- the method may further comprise providing from about 0.1 to about 10 percent by weight based on a weight of the lubricant composition of at least one metal protective additive.
- the present invention relates generally to lubricant compositions useful for high temperature applications comprising polyol polyesters derived from 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid and reaction products, mixtures, and copolymers thereof. It should be understood based on this disclosure hereinafter that when referring to "5,7,7-uitnethyl-2-(1,3,3-trimethylbutyl)-octanoic acid" herein included within the scope thereof arc reaction products, mixtures and copolymers thereof.
- the present invention provides lubricant compositions that exhibit high resistance to thermal and/or oxidative breakdown and/or polymerization, low volatility, and a low deposit formation tendency.
- lubricant compositions include, but are not limited to, those that include the reaction product of at least one neopentyl polyol and 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid.
- lubrication compositions that include an additive that is the reaction product of at least one neopentyl polyol and 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid as well as mixtures, reaction products and copolymers of that reaction product.
- base oils are provided which are a mixture of the reaction product of at least one neopentyl polyol and 5,7,7-trimethyl-2-(1,3,3-tritnethylbutyl)-octanoic acid, and at least one additional base oil such as other base compositions including various mixtures of the reaction product noted above with at least one additional base oil, at least one metal protecting additive and/or at least one lubricant protecting additive.
- reaction product noted above When used as a base oil to a lubricant composition, it is used in amounts of about 0.5 to about 99.5 percent by we ight of the composition, more preferably about 1 to about 95 percent by weight or about 5 to about 95 weight percent, and most preferably about 5 to about 50 weight percent, wherein the weight percentages are based on the total weight percent of the lubricant composition.
- additional base oils may be used in similar quantities, and for example also in amounts of from 50 to 90 percent of the lubricant composition, and may be preferably a poly ⁇ - olefin, and preferably, when the base oil including the reaction product is about 5 to about 50 weight percent of the composition, the additional base oil(s) make up about 50 to about 90 percent of the lubricant composition.
- the ratio of the base oil having the reaction product to the additional base oils is preferably from about 99:1 to about 1:99, more preferably 25:75 to about 75:25, still more preferably about 30:70 to about 70:30, and most preferably about 50:50.
- Alkyl substituents contribute electron density and stabilize free radicals. Tertiary hydrogen atoms are most easily abstracted, followed by secondary, then primary. The exact position of alkyl groups within a carbon chain can also have the effect of either stabilizing or de-stabilizing the molecule by steric crowding, or by eliminating the possibility of non-oxidative degradation reactions such as dehydration that can give rise to by-products that are easily oxidized.
- this carboxylic acid possesses eighteen (18) carbon atoms, eight (8) sterically crowded secondary hydrogen atoms, two (2) highly sterically crowded tertiary hydrogen atoms, and one (1) tertiary hydrogen atom adjacent to the carboxylic acid. All other hydrogens within this molecule are primary. The hydrogen atoms located in close proximity to the ester linkages are more difficult to extract. Neopentyl polyols possess only primary hydrogen, atoms.
- One embodiment of the present invention is a lubricant composition, including as a base oil and/or a liquid, a polyol polyester formed as the reaction product of, preferably from the esterification of, at least one neopentyl polyol and 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid.
- the composition may also include further reaction products, mixtures or copolymers of the reaction product noted above.
- the preferred polyol polyester has a viscosity of from about 100 centistokes to about 25,000 centistokes when measured at 40°C. More particularly, the polyol used to make the polyol polyester is a neopentyl polyol.
- neopentyl polyols include, but are not limited to, neopentyl glycol, trimelhylolpropane, trimethylolethane, monopentaerythritol, ditrimethylolpropane, dipentaerythritol tripentaerythritol, and tetrapentaerythritol.
- neopentyl polyols are commercially available, however, it is within the scope of the invention to use both commercially available neopentyl polyols as well as synthesized or modified neopentyl polyols.
- Preferred polyols are monopentaerythrical and trimethylolpropane or combinations thereof, although minor quantities of dipentaerythritol, tripentaerythritol, and tetrapentaerythritol may be utilized in combination or admixture therewith.
- the invention encompasses a base oil that includes a mixture of a liquid polyol polyester formed from the esterification of at least one neopentyl polyol and 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid (and its variations as noted above) and at least one additional base oil.
- Preferred additional base oils include those known or to be developed in the lubricant arts, such as, for example, synthetic esters, polyesters, complex polyol polyester polymers, poly ⁇ -olefins, polymer esters, such as, for example, Ketjenlube®, commercially available from Akzo Nobel, alkylated naphthalenes, polyalkylene glycols, silicones, phosphate esters, alkylated aromatics, silahydrocarbons, phosphazenes, polyphosphazenes, dialkylcarbonates, cycloaliphatics, polybutenes, alkyldiphenyl ethers, polyphenyl ethers, mineral oils, hydrocarbon oils, triglyceride oils, vegetable oils, fatty acids having a primary carbon chain length of about 5 to about 54 carbon atoms, and copolymers, mixtures, derivatives, and combinations of these materials.
- synthetic esters such as, for example, synthetic esters, polyesters, complex polyo
- Synthetic esters may include, but are not Limited to, neopentyl polyol esters, complex polyol polyesters, and aromatic esters.
- Preferred synthetic esters are neopentyl polyol polyesters and/or neopentyl polyol polyester polymers.
- Neopentyl polyol polyesters referred to herein are the reaction products of neopentyl polyols with at least one monofunctional carboxylic acid, and having multiple ester linkages in the molecule. Such materials are typically not polymeric in character.
- Neopentyl polyol polyester polymers are the reaction products of neopentyl polyols and at least one polyfunctional carboxylic acid and at least one monofunctional carboxylic acid and/or a monofunctional alcohol as an end capper. Such materials are polymeric in character and are also known as complex esters or complex polyol esters.
- Preferred neopentyl polyol polyesters include the reaction products of neopentyl polyols with linear and/or branched carboxylic acids of chain length of about 5 to about 12 carbon atoms.
- Preferred neopentyl polyol polyester polymer include the reaction products of at least one neopentyl polyol, at least one polycarboxylic acid, and at least one linear and/or branched monocarboxylic acid and/or alcohol of chain length of about 5 to about 20 carbon atoms.
- Such lubricant compositions preferably include such as, for example, metal protecting additives t-butylphenyl phosphates, amines; branched alkyls of from 11 to 14 carbon atoms, monahexyl and dihexyl phosphates, isopropylphenylphosphates, tricresyl phosphates, trixylyl phosphates, di(n-octyl)phosphite, alkylated triphenylphosphorothionate, triphenylthiophosphate, benzotriazole, tolyltriazole, and mixtures, derivatives, and combinations thereof.
- metal protecting additives t-butylphenyl phosphates, amines
- branched alkyls of from 11 to 14 carbon atoms monahexyl and dihexyl phosphates
- isopropylphenylphosphates tricresyl phosphates
- At least one metal protecting additive is preferably used when provided such an optional additive to a preferred lubricant composition. More particularly, up to about 5 percent by weight of the lubricant composition of metal protecting additive is provided to the lubricant composition.
- Lubricant protecting additives include any such additive known or to be developed in the lubricant art, but are not limited to, benzenamine, N-phenyl-, reaction products with 2,4,4-trimethylpentene; N-phenyl-1,1,3,3-tetramethylbutylnaphthalen-1-amine; butylated hydroxytoluene; alkylated diphenylamine; nonylated diphenylamine; styrenated diphenylanzine; hindered alkylphenols; benzenepropanoic acid, 3,5-bis(1,1-dimethylathyl)-4-hydroxy-, thiodi-2,7-ethanediyl ester, benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-, 2,2-bis[[3-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1-oxopropoxy]methyl]
- thiophenolic derivatives and mixtures, derivatives, and combinations of these materials.
- About 0.5 to about 15 percent by weight of at least one lubricant protecting additive is preferably added to the lubricant composition. More particularly, up to about 5 percent by weight of an optional lubricant protecting additive is provided to the lubricant composition.
- kinematic viscosity was tested using ASTM International, West Conshohocken, Pennsylvania, USA, (standard test method ASTM-D-445-97 (1997).
- Total acid number (TAN) was determined using ASTM D-972.
- Hydroxyl value (OH) was determined using ASTM D-1957.
- Viscosity index (VI) was determined using ASTM D-2270. Flash point was determined using ASTM D-92, and pour point was determined using ASTM D-97.
- Evaporation loss, deposit formation tendency, and residual oil fluidity were assessed by the following procedure.
- the lubricant base oil was blended with 1.5 wt% each of benzenamine, N-phenyl-, reaction products with 2,4,4-trimethylpentene (Vanlube® 81, commercially available from RT Vanderbilt Corporation, Norwalk, Connecticut, USA) and N-phenyl-1,1,3,3-tetramethylbutylnaphthalen-1-amine (Irganox® LO-6, commercially available for Ciba Specialty Chemicals Corporation, Tarrytown, New York, USA).
- Two (2) grams of lubricant liquid were placed in an aluminum weighing dish, and then placed in a muffle furnace. The test condition of 288°C was held for 5 1 ⁇ 2 hours. Evaporation loss, deposit formation tendency, and flow properties of the lubricant after this procedure were measured by weight and by visual observation, respectively.
- the lubricant composition trimethylolpropane tri-5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoate was prepared by combining the following materials of Table 1 in a batch reactor fitted with a mechanical stirrer; inert gas sparge, vapor column, condenser, and distillate receiver. Pressure in the reactor was controlled by a vacuum pump that was attached to the reactor. TABLE 1 Component Parts Per 100 Parts Moles Per 100 Parts Trimethylolpropane 13.6 0.101 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid 86.4 0.304
- TMPPETTBO Trimethylolpropane/Pentaerythritol 5,7,7-trimcthyl-2-(1,3,3-trimethylbutyl)-octanoate
- a lubricant base oil was prepared by combining the following ingredients of Table 5: TABLE 5 Component Parts Per 100 Parts TMPTTBO 50 Synthetic Ester 50
- a lubricant base oil was prepared by combining the following ingredients of Table 7: TABLE 7 Component Parts Per 100 Parts TMPTTBO 57 Synthetic Ester 43
- a lubricant base oil was prepared by combining the following ingredients of Table 9: TABLE 9 Component Parts Per 100 Parts TMPTTBO 15 Synthetic Ester 85
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Description
- Lubricants that can maintain their structure under extremes of temperature are useful and essential in many commercial, domestic, and industrial applications. Such applications include, but are not limited to, fiberglass production, wood laminating, wood pressing, paint curing, textile production, and food baking. Lubricants can also be used in aerospace applications in which fluids are exposed to temperatures typically exceeding 200°C. Such high temperature lubrication fluids must also provide sufficient lubrication of metal surfaces to prevent wear, reduce friction, reduce energy consumption, and more importantly, prevent failure of mechanical systems.
- Lubricants that are used at high temperatures must also be resistant to thermal and/or oxidative breakdown and polymerization. Thermal and/or oxidative breakdown leads to the scission of lubricant molecules, which in turn, leads to the formation of lower molecular weight compounds that can be volatilized, depending upon the operational conditions of a mechanical system. This process normally results in an increased lubricant viscosity. Where the lubricant is exposed to the atmosphere, and especially in thin films, an increase in lubricant viscosity reduces the mobility of the lubricant liquid, accelerates oxidation, and leads to the formation of deposits. Such breakdown may also result in loss of lubricant fluid and/or the production of excessive vapors and/or smoke, or ineffective lubrication. This, in turn, can lead to mechanical breakdown, higher energy consumption, reduced cleanliness, poorer product quality, and higher occupational exposure to volatile organic compounds. Polymerization can lead to formation of deposits of semi-solid gums and hard varnishes that can build up on metal surfaces and in work environments. This, in turn, may lead to poorer lubrication, higher energy consumption, and potential production stoppages due to the need to remove deposits from the metal surfaces.
- Liquid lubricant compositions typically have a base oil to which other additives are provided. The additives impart specific properties to the overall lubricant mixture. One class of such additives is metal protecting additives. These exhibit beneficial properties such as resistance to wear, protection from damage at extreme pressure, and resistance to corrosion. Such additives are also useful for protecting metal surfaces. One drawback of metal protecting additives, however, is that they can reduce stability of the base oils once added.
- To alleviate such loss of stability, lubricant protecting additives can be provided to the base oils. Lubricant protecting additives are helpful for maintaining a lubricant's structure under operational conditions. The most important lubricant protecting additives are antioxidants. Antioxidants protect a base oil in a lubricant composition and/or other additives therein from attack by atmospheric oxygen, a harmful process also known as oxidation, which produces unwanted free radicals and leads to instability. Antioxidants help to stabilize base oils by helping to prevent oxidation. The effectiveness of antioxidants is strongly influenced by the level of stability of the base oil or oils in the composition. Greater stability of the base oil helps to reduce potentially adverse effects of oxidation.
- A few types of compounds are mutinely used as liquid base oils in the field of high temperature lubricants, include perfluoropolyalkyl ethers which are highly resistant to oxidation due to the complete absence of extractable hydrogen atoms. Polyphenylethers and alkyldiphenyl ethers are also inherently very stable. However, their lubrication properties are poorer than other classes of base oils, and they tend to be either incompatible and/or not positively responsive to metal and/or lubricant protecting additives. Additionally, due to the sophisticated synthesis techniques and manufacturing processes required to produce these materials, they are only produced in small quantities unsuitable for large-scale industrial use.
- Another class of compounds commonly used as liquid base oils in the lubrication field is synthetic esters. Synthetic esters are derived from the reaction of carboxylic acids and alcohols. Carboxylic acids and alcohols can be synthesized to very high purity, and thus, synthetic esters can be designed with very defined structures that can be targeted to provide the specific properties sought in a particular application. Synthetic esters are generally both compatible with, and respond favorably to common metal and lubricant protecting additives.
- Esters of certain carboxylic acids and alcohols are known to possess enhanced resistance to thermal and/or oxidative breakdown. Two general classes of commonly used synthetic esters with one or more of these properties are aromatic esters and neopolyol esters. Aromatic esters are formed as a reaction product of aromatic polycarboxylic acids, such as trimellitic acid and pyromellitic acid, and linear and/or branched monofunctional alcohols. Such alcohols typically have a carbon chain length of about 8 to about 13 carbon atoms. Although aromatic esters are prone to oxidationdue to the aromatic portion of the molecule, they can be useful due to their relatively high molecular weight and structural purity that contributes to a lower volatility.
U.S. Patent No. 6,465,400 discloses a lubricant composition prepared by mixing aromatic esters with an additional base oil and antioxidants. - Neopolyol esters are formed from the reaction of neopentyl polyols, such as neopentyl glycol, trimethylolpropane, pentaerythritol, and dipentaerythritol with linear and/or branched carboxylic acids that are typically about two to about ten carbon atoms in chain length. Neopolyol esters as a class are generally more resistant to oxidation than aromatic esters. They are particularly useful due to their higher thermal and oxidative stability which stems from the absence of hydrogens attached to carbons that are β to the ester linkage, which can lead to a low energy oxidation pathway. The carboxylic acids used to form such esters typically are linear and/or branched chain acids having from about five to about ten carbon atoms.
U.S. Patent No. 4,826,633 discloses esters formed by reacting trimethylolpropane and monopentaerythritol with a mixture of linear and branched carboxylic acids having from 5 to 10 carbon atoms.U.S: Patent No. 6,436,981 discloses a high temperature lubricant formulation formed by reacting mainly dipentaerythritol with a mixture of linear and branched carboxylic acids having from 5 to 12 carbon atoms, that also includes a viscosity index improver.U.S. Patent No. 6,884,861 discloses a high temperature lubricant composition including esters formed from the reaction of certain polyols with mixtures of carboxylic acids having a five to ten carbon chain length and/or aromatic acids.US4477383 discloses neopentyl polyol ester of isostearic acid as Lubricant base stock. - Neopentyl polyol polyesters that are formed from certain relatively short chain linear or branched carboxylic acids of about 5 to about 10 carbons are particularly resistant to thermal and/or oxidative breakdown and/or polymerization relative to neopentyl polyol polyesters derived from longer chain carboxylic acids of about 12 carbons and longer. Examples of shorter chain carboxylic acids employed for forming neopentyl polyol polyester for use as base oils in lubricant compositions are pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, 2-ethylhexanoic acid, nonanoic acid, 3,5,5-trimethylhexanoic acid (isononanoic acid) and decanoic acid. The shorter chain carboxylic acids are preferred due to the shielding effect provided by the ester linkage that makes the hydrogen atoms on the carboxylic acid portion more resistant to abstraction and resultant oxidative attack. Longer chain carboxylic acids generally possess hydrogen atoms further away from the ester linkage that do not benefit from increased stability provided from the shielding effect of the ester linkage.
- Although using shorter chain carboxylic acids improves resistance to oxidation, the resulting molecular weight of the ester is typically limited, which can lead to higher volatility. Isononanoic acid is particularly resistant to oxidation due to the reduced presence of secondary hydrogen atoms and the steric crowding about the lone tertiary hydrogen atom. However, due to its highly branched nature, the resulting esters generally have higher volatility. Higher volatility of the base ester, and resulting oxidative scission products can lead to oil thickening that accelerates the formation of deposits, especially in thin films.
- Therefore, there is a need in the art for an improved ester that combines the desirable thermal and oxidative stability typically provided by the reaction of neopentyl polyols with shorter chain carboxylic acids; the low volatility and/or low volatility of oxidation scission products, which, in the past, have been associated with the use of longer chain carboxylic acids to form the neopentyl polyol ester; and the low volatility that arises from the use of aromatic polycarboxylic acids to form the aromatic ester.
- The present invention includes a lubricant composition that has at least one polyol polyester. The polyol polyester is the reaction product of at least one neopentyl polyol and 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid which reaction product is present in the lubricant composition in an amount of from 0.5 to 99.5% by weight of the lubricant composition based on the total weight of the lubricant composition.
- In one embodiment, the reaction product is a base oil in a lubricant composition. In a further embodiment, the lubricant composition including the reaction product as a base oil comprises at least one additional base oil. In yet a further embodiment, the lubricant composition including the reaction product as a base oil and comprising at least one additional base oil further comprises a lubricant protecting additive and/or a metal protecting additive.
- One embodiment of the present invention includes providing a lubricant composition that has at least one polyol polyester. The polyol polyester is the reaction product of a neopentyl polyol and 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid. The reaction product is a base oil in the composition, and the composition also has at least one additional base oil.
- The invention also includes a lubricant composition that has at least one polyol polyester. The polyol polyester is the reaction product of a neopentyl polyol and 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid. The reaction product is a base oil in the composition, and the composition further also has at least one additional base oil, at least one metal protecting additive, and/or at least one lubricant protecting additive.
- Also included herein is a method of lubricating a metal surface. The method comprises applying a lubricant composition to a metal surface, wherein the lubricant composition comprises a) a reaction product of at least one neopentyl polyol and 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid wherein the reaction product is a base oil in the composition, b) at least one additional base oil, c) from about 0.5 to about 15 percent by weight of at least one lubricant protecting additive, and d) from about 0.1 to about 10 percent by weight of at least one metal protecting additive.
- Further, a method of making a lubricant composition, is included. The method comprises reacting a) at least one neopentyl polyol and b) 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid wherein the reaction product is a base oil in the composition.
- The method may further comprise providing at least one additional base oil. The base oil can be present in an amount of from 5 to about 50 percent by weight of the lubricant composition and the additional base oil is present from about 50 to 90 percent of the lubricant composition. Preferably the method may further comprise providing from about 0.5 to about 15 percent by weight based on a weight of the lubricant composition of at least one lubricant protective additive. Also preferable the method may further comprise providing from about 0.1 to about 10 percent by weight based on a weight of the lubricant composition of at least one metal protective additive.
- The present invention relates generally to lubricant compositions useful for high temperature applications comprising polyol polyesters derived from 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid and reaction products, mixtures, and copolymers thereof. It should be understood based on this disclosure hereinafter that when referring to "5,7,7-uitnethyl-2-(1,3,3-trimethylbutyl)-octanoic acid" herein included within the scope thereof arc reaction products, mixtures and copolymers thereof.
- The present invention provides lubricant compositions that exhibit high resistance to thermal and/or oxidative breakdown and/or polymerization, low volatility, and a low deposit formation tendency. Examples of such lubricant compositions include, but are not limited to, those that include the reaction product of at least one neopentyl polyol and 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid. In addition, it jncludes lubrication compositions that include an additive that is the reaction product of at least one neopentyl polyol and 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid as well as mixtures, reaction products and copolymers of that reaction product. Further, base oils are provided which are a mixture of the reaction product of at least one neopentyl polyol and 5,7,7-trimethyl-2-(1,3,3-tritnethylbutyl)-octanoic acid, and at least one additional base oil such as other base compositions including various mixtures of the reaction product noted above with at least one additional base oil, at least one metal protecting additive and/or at least one lubricant protecting additive.
- When the reaction product noted above is used as a base oil to a lubricant composition, it is used in amounts of about 0.5 to about 99.5 percent by we ight of the composition, more preferably about 1 to about 95 percent by weight or about 5 to about 95 weight percent, and most preferably about 5 to about 50 weight percent, wherein the weight percentages are based on the total weight percent of the lubricant composition. If additional base oils are provided, they may be used in similar quantities, and for example also in amounts of from 50 to 90 percent of the lubricant composition, and may be preferably a poly α - olefin, and preferably, when the base oil including the reaction product is about 5 to about 50 weight percent of the composition, the additional base oil(s) make up about 50 to about 90 percent of the lubricant composition. The ratio of the base oil having the reaction product to the additional base oils is preferably from about 99:1 to about 1:99, more preferably 25:75 to about 75:25, still more preferably about 30:70 to about 70:30, and most preferably about 50:50.
- The mechanism of oxidation (autoxidation) is commonly described by the "hydroperoxide theory." The hydropcroxide theory in its most basic form can be summarized in the series of reaction steps depicted below:
Step Reaction formation of free radical RH → R• + •H formation of peroxy radical R• + O2 → ROO• formation of hydroperoxide ROO• + RH → ROOH + R• Propagation ROOH → RO• + •OH RO• + RH → ROH + R• HO• + RH → HOH + R• - Depending upon the nature of the substrate chemical, the specific course of reaction, the kinetics of the reaction, the rate dependency upon temperature, or the presence of metal catalysts, enzymes, or ultraviolet radiation that can impact the reaction kinetics, a virtually infinite variety of by-products may be observed. Based upon this theory, the primary factor in the prediction of oxidation stability when inspecting a molecular structure is the identification of hydrogen atoms that may be easily abstracted to form free radicals. Since free radicals are formed chemically by homolytic cleavage of carbon-hydrogen bonds, a first estimate can be obtained simply by looking at bond dissociation energies.
- Alkyl substituents contribute electron density and stabilize free radicals. Tertiary hydrogen atoms are most easily abstracted, followed by secondary, then primary. The exact position of alkyl groups within a carbon chain can also have the effect of either stabilizing or de-stabilizing the molecule by steric crowding, or by eliminating the possibility of non-oxidative degradation reactions such as dehydration that can give rise to by-products that are easily oxidized.
-
- As can be seen from the structure, this carboxylic acid possesses eighteen (18) carbon atoms, eight (8) sterically crowded secondary hydrogen atoms, two (2) highly sterically crowded tertiary hydrogen atoms, and one (1) tertiary hydrogen atom adjacent to the carboxylic acid. All other hydrogens within this molecule are primary. The hydrogen atoms located in close proximity to the ester linkages are more difficult to extract. Neopentyl polyols possess only primary hydrogen, atoms.
- One embodiment of the present invention is a lubricant composition, including as a base oil and/or a liquid, a polyol polyester formed as the reaction product of, preferably from the esterification of, at least one neopentyl polyol and 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid. The composition may also include further reaction products, mixtures or copolymers of the reaction product noted above. The preferred polyol polyester has a viscosity of from about 100 centistokes to about 25,000 centistokes when measured at 40°C. More particularly, the polyol used to make the polyol polyester is a neopentyl polyol. Such neopentyl polyols include, but are not limited to, neopentyl glycol, trimelhylolpropane, trimethylolethane, monopentaerythritol, ditrimethylolpropane, dipentaerythritol tripentaerythritol, and tetrapentaerythritol. Such neopentyl polyols are commercially available, however, it is within the scope of the invention to use both commercially available neopentyl polyols as well as synthesized or modified neopentyl polyols. Preferred polyols are monopentaerythrical and trimethylolpropane or combinations thereof, although minor quantities of dipentaerythritol, tripentaerythritol, and tetrapentaerythritol may be utilized in combination or admixture therewith.
- In one embodiment, the invention encompasses a base oil that includes a mixture of a liquid polyol polyester formed from the esterification of at least one neopentyl polyol and 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid (and its variations as noted above) and at least one additional base oil. Preferred additional base oils include those known or to be developed in the lubricant arts, such as, for example, synthetic esters, polyesters, complex polyol polyester polymers, poly α-olefins, polymer esters, such as, for example, Ketjenlube®, commercially available from Akzo Nobel, alkylated naphthalenes, polyalkylene glycols, silicones, phosphate esters, alkylated aromatics, silahydrocarbons, phosphazenes, polyphosphazenes, dialkylcarbonates, cycloaliphatics, polybutenes, alkyldiphenyl ethers, polyphenyl ethers, mineral oils, hydrocarbon oils, triglyceride oils, vegetable oils, fatty acids having a primary carbon chain length of about 5 to about 54 carbon atoms, and copolymers, mixtures, derivatives, and combinations of these materials.
- Synthetic esters may include, but are not Limited to, neopentyl polyol esters, complex polyol polyesters, and aromatic esters. Preferred synthetic esters are neopentyl polyol polyesters and/or neopentyl polyol polyester polymers. Neopentyl polyol polyesters referred to herein are the reaction products of neopentyl polyols with at least one monofunctional carboxylic acid, and having multiple ester linkages in the molecule. Such materials are typically not polymeric in character. Neopentyl polyol polyester polymers are the reaction products of neopentyl polyols and at least one polyfunctional carboxylic acid and at least one monofunctional carboxylic acid and/or a monofunctional alcohol as an end capper. Such materials are polymeric in character and are also known as complex esters or complex polyol esters.
- Preferred neopentyl polyol polyesters include the reaction products of neopentyl polyols with linear and/or branched carboxylic acids of chain length of about 5 to about 12 carbon atoms. Preferred neopentyl polyol polyester polymer include the reaction products of at least one neopentyl polyol, at least one polycarboxylic acid, and at least one linear and/or branched monocarboxylic acid and/or alcohol of chain length of about 5 to about 20 carbon atoms.
- Such lubricant compositions preferably include such as, for example, metal protecting additives t-butylphenyl phosphates, amines; branched alkyls of from 11 to 14 carbon atoms, monahexyl and dihexyl phosphates, isopropylphenylphosphates, tricresyl phosphates, trixylyl phosphates, di(n-octyl)phosphite, alkylated triphenylphosphorothionate, triphenylthiophosphate, benzotriazole, tolyltriazole, and mixtures, derivatives, and combinations thereof.
- About 0.1 to about 10 percent by weight of the total composition of at least one metal protecting additive is preferably used when provided such an optional additive to a preferred lubricant composition. More particularly, up to about 5 percent by weight of the lubricant composition of metal protecting additive is provided to the lubricant composition.
- Lubricant protecting additives include any such additive known or to be developed in the lubricant art, but are not limited to, benzenamine, N-phenyl-, reaction products with 2,4,4-trimethylpentene; N-phenyl-1,1,3,3-tetramethylbutylnaphthalen-1-amine; butylated hydroxytoluene; alkylated diphenylamine; nonylated diphenylamine; styrenated diphenylanzine; hindered alkylphenols; benzenepropanoic acid, 3,5-bis(1,1-dimethylathyl)-4-hydroxy-, thiodi-2,7-ethanediyl ester, benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-, 2,2-bis[[3-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1-oxopropoxy]methyl]-1,3-propanediyl ester;
- thiophenolic derivatives, and mixtures, derivatives, and combinations of these materials. About 0.5 to about 15 percent by weight of at least one lubricant protecting additive is preferably added to the lubricant composition. More particularly, up to about 5 percent by weight of an optional lubricant protecting additive is provided to the lubricant composition.
- The invention will now be explained with respect to the following, non-limiting Examples. In the following Examples, kinematic viscosity was tested using ASTM International, West Conshohocken, Pennsylvania, USA, (standard test method ASTM-D-445-97 (1997). Total acid number (TAN) was determined using ASTM D-972. Hydroxyl value (OH) was determined using ASTM D-1957. Viscosity index (VI) was determined using ASTM D-2270. Flash point was determined using ASTM D-92, and pour point was determined using ASTM D-97.
- Evaporation loss, deposit formation tendency, and residual oil fluidity were assessed by the following procedure. The lubricant base oil was blended with 1.5 wt% each of benzenamine, N-phenyl-, reaction products with 2,4,4-trimethylpentene (Vanlube® 81, commercially available from RT Vanderbilt Corporation, Norwalk, Connecticut, USA) and N-phenyl-1,1,3,3-tetramethylbutylnaphthalen-1-amine (Irganox® LO-6, commercially available for Ciba Specialty Chemicals Corporation, Tarrytown, New York, USA). Two (2) grams of lubricant liquid were placed in an aluminum weighing dish, and then placed in a muffle furnace. The test condition of 288°C was held for 5 ½ hours. Evaporation loss, deposit formation tendency, and flow properties of the lubricant after this procedure were measured by weight and by visual observation, respectively.
- The lubricant composition trimethylolpropane tri-5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoate (TMPTTBO) was prepared by combining the following materials of Table 1 in a batch reactor fitted with a mechanical stirrer; inert gas sparge, vapor column, condenser, and distillate receiver. Pressure in the reactor was controlled by a vacuum pump that was attached to the reactor.
TABLE 1 Component Parts Per 100 Parts Moles Per 100 Parts Trimethylolpropane 13.6 0.101 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid 86.4 0.304 - About 0.10 parts per 100 parts tetrabutyltitanate was added to the reaction mixture, and the mixture was heated to from about 180°C to about 250°C. Pressure was slowly reduced until sufficient conversion was obtained The crude ester was further purified by steam distillation and filtration. The result was a yellow viscous liquid possessing the following properties shown in Table 2:
TABLE 2 Property, Units Teat method Result Total Acid Number, mg KOH/g ASTM D-972 0.38 Hydroxyl Number, mg KOH/g ASTM D-1957 4.7 Kinematic Viscosity @ 40°C, cSt ASTM D-445 2,411 Kinematic Viscosity @ 100°C, cSt ASTM D-445 44.6 Viscosity Index ASTM D-2270 -22 Flash Point (C.O.C), °C ASTM D-92 280 Evaporation Loss, % 48.8 Deposits After Heating, Visual Minimal Fluidity After Heating, Visual Fluid - The lubricant composition Trimethylolpropane/Pentaerythritol 5,7,7-trimcthyl-2-(1,3,3-trimethylbutyl)-octanoate (TMPPETTBO) was prepared by combining the following materials in Table 3 in a batch reactor fitted with a mechanical stirrer, inert gas sparge, vapor column, condenser, and distillate receiver. Pressure in the reactor was controlled by a vacuum pump that was attached to the reactor.
TABLE 3 Component Parts Per 100 Parts Moles Per 100 Parts Trimethylolpropane 9.5 0.071 Pentaerythritol 3.2 0.024 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid 87.3 0.307 - About 0.10 parts per 100 parts tetrabutyltitanate was added to the reaction mixture, and the mixture was heated to from about 180°C to about 250°C. The pressure was slowly reduced until sufficient conversion was obtained. The crude ester was further purified by stream distillation and filtration. The result was a yellow viscous liquid possessing the following properties listed in Table 4:
TABLE 4 Property, Units Test Method Result Total Acid Number, mg KOH/g ASTM D-972 0.31 Hydroxy Number, mg KOH/g ASTM D-1957 0.42 Kinematic Viscosity @ 40°C, cSt ASTM D-445 3,157 Kinematic Viscosity @ 100°C, cSt ASTM D-445 53.8 Viscosity Index ASTM D-2270 -8 Flash Point (C.O.C), °C ASTM D-92 286 Evaporation Loss, % 44.1 Deposit After Heating, Visual Minimal Fluidity After Heating, Visual Fluid - A lubricant base oil was prepared by combining the following ingredients of Table 5:
TABLE 5 Component Parts Per 100 Parts TMPTTBO 50 Synthetic Ester 50 - The result was a yellow viscous liquid possessing the following properties shown in Table 6:
TABLE 6 Property, Units Test Method Result Total Acid Number, mg KOH/g ASTM D-972 0.17 Hydroxyl Number, mg KOH/g ASTM D-1957 4.5 Kinematic Viscosity @ 40°C, cSt ASTM D-445 401.4 Kinematic Viscosity @100°C, cSt ASTM D-445 20.0 Viscosity Index ASTM D-2270 35 Flash Point (C.O.C), °C ASTM D-92 270 . Pour Point, °C ASTM D-97 -15 Evaporation Loss, % 58.7 Deposits After Heating, Visual Minimal Fluidity After Heating, Visual Fluid - A lubricant base oil was prepared by combining the following ingredients of Table 7:
TABLE 7 Component Parts Per 100 Parts TMPTTBO 57 Synthetic Ester 43 - The result was a yellow viscous liquid possessing the following properties of Table 8:
TABLE 8 Property, Units Test Method Result Total Acid Number, mg KOH/g ASTM D-972 0.26 Hydroxyl Number, mg KOH/g ASTM D-1957 4.57 Kinematic Viscosity @ 40°C, cSt ASTM D-445 363.0 Kinematic Viscosity @ 100°C, cSt ASTM D-445 20.8 Viscosity Index ASTM D-2270 58 Flash Point (C.O.C), °C ASTM D-92 290 Pour point, °C ASTM D-97 -21 Evaporation Loss, % 40.8 Deposits After Heating, Visual Minimal Fluidity After Heating, Visual Fluid - A lubricant base oil was prepared by combining the following ingredients of Table 9:
TABLE 9 Component Parts Per 100 Parts TMPTTBO 15 Synthetic Ester 85 - The result was a yellow viscous liquid possessing the following properties of Table 10:
TABLE 10 Property, Units Test Method Result Total Acid Number, mg KOH/g ASTM D-972 0.06 Hydroxyl Number, mg KOH/g ASTM D-1957 1.9 Kinematic Viscosity @ 40°C, cSt ASTM D-445 489 Kinematic Viscosity @ 100°C, cSt ASTM D-445 27.0 Viscosity Index ASTM D-2270 27 Flash Point (C.O.C), °C ASTM D-92 306 Pour Point, °C ASTM D-97 -18 Evaporation Loss, % 71.5 Deposits After Heating, Visual Minimal Fluidity After Heating, Visual Fluid - To illustrate the improvement that can be made by use of TMPTTBO as an additive, the following mixtures of Table 11 were prepared by blending the fluids at about 70 to about 90°C with mechanical agitation until a clear uniform solution was obtained.
TABLE 11 Component Mixture A Parts Per 100 Parts Mixture B Parts Per 100 Parts TMPTTBO 29.1 --- Poly α-olefin 40 67.9 58.2 Poly α-olefin 100 --- 38.8 Vanlube® 81 1.5 1.5 Irganox® LO-6 1.5 1.5 - The solutions were then tested for thin film heat stability. Two grams of lubricant were placed in an aluminum weighing dish, placed in a muffle furnace, and held for a test duration of 5 ½ hours at 288°C. Evaporation loss, deposits, and flow properties of the lubricant after the test were measured by weight and by visual observation, respectively.
- The results are provided bolow in Table 12:
TABLE 12 Property, Units Mixture A Mixture B Evaporation Loss, % 21.7 31.3 Deposits After Heating, Visual Minimal Significant Fluidity After Heating, Visual Fluid Non Fluid Tar
Claims (15)
- A lubricant composition comprising at least one polyol polyester, which polyol polyester is the reaction product of:a) at least one neopentyl polyol, andb) 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acidwhich reaction product is present in the lubricant composition in an amount of from 0.5 to 99.5 % by weight of the lubricant composition, based on the total weight of the lubricant composition.
- The lubricant composition of claim 1, wherein the neopentyl polyol is selected from the group consisting of neopentyl glycol, trimethylolpropane, trimethylolethane, monopentaerythritol, ditrimethylolpropane, dipentaerythritol, tripentaerythritol, and tetrapentaerythritol.
- The lubricant composition of claim 1, wherein the reaction product is a base oil in the composition and the composition further comprises at least one additional base oil.
- The lubricant composition of claim 3, wherein the base oil is from 1 to 95 percent by weight of the lubricant composition and the additional base oil is 1 to 95 percent of the lubricant composition.
- The lubricant composition of claim 4, wherein the additional base oil is a synthetic ester selected from the group consisting of neopentyl polyol esters, complex polyol polyesters, alkylated naphthalenes and aromatic esters.
- The lubricant composition of claim 1, further comprising from 0.5 to 15 percent by weight based on a weight of the lubricant composition of at least one lubricant protecting additive.
- The lubricant composition of claim 6, wherein the lubricant protecting additive is present in the amount of up to 5 percent by weight based on the weight of the lubricant composition.
- The lubricant composition of claim 6, wherein the lubricant protecting additive is selected from the group consisting of benzenamine, N-phenyl-, reaction products with 2,4,4-trimethylpentene; N-phenyl-1,1,3,3-tetramethylbutylnaphthalen-1-amine; butylated hydroxytoluene; alkylated diphenylamine; nonylated diphenylamine; styrenated diphenylamine; hindered alkylphenols; benzenepropanoic acid; 3,5-bis(1,1-dimethylethyl)-4-hydroxy-, thiodi-2,1-ethanediyl ester; benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-, 2,2-bis[[3-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1-oxapropoxy]methyl]-1,3-propanediyl ester; thiophenolic derivatives; and mixtures; derivatives; and combinations thereof.
- The lubricant composition of claim 1, further comprising from 0.1 to 10 percent by weight of at least one metal protecting additive based on a weight of the lubricant composition.
- The lubricant composition of claim 9, wherein the metel protecting additive is present in the amount of up to 5 percent by weight based on the weight of the lubricant composition.
- The lubricant composition of claim 9, wherein the metal protecting additive is selected from the group consisting of t-butylphenyl phosphates, amines; branched alkyls of from 11 to 14 carbon atoms, monohexyl and dihexyl phosphates, isopropylphenylphosphates; tricresyl phosphates; trixylyl phosphates; di(n-octyl)phosphate; alkylated triphenylphosphorothionate: triphenylthiophosphate; benzotriazole; tolyltriazole; and mixtures; derivatives; and combinations thereof.
- A method of lubricating a metal surface, comprising:applying a lubricant composition to a metal surface, wherein the lubricant composition comprises:a) a reaction product of at least one neopentyl polyol and 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid wherein the reaction product is a base oil in the composition,b) from 0.5 to 15 percent by weight of at least one lubricant protecting additive, andc) from 0.1 to 10 percent by weight of at least one metal protecting additive.
- The method of lubricating, according to claim 12, wherein the lubricant composition further comprises at least one additional base oil.
- The method of lubricating, according to claim 13, wherein the lubricant composition comprises 5 to 50 percent of the reaction product (a) and 50 to 90 percent of the at least one additional base oil.
- A method of making a lubricant composition, comprising reactinga) at least one neopentyl polyol andb) 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid wherein the reaction product is a base oil in the composition.
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KR19990063738A (en) * | 1995-09-25 | 1999-07-26 | 가오가부시끼가이샤 | Ester compounds and lubricating oil composition |
JP3608597B2 (en) * | 1996-12-27 | 2005-01-12 | 東燃ゼネラル石油株式会社 | Lubricating oil composition for internal combustion engines |
ATE246239T1 (en) * | 1997-10-01 | 2003-08-15 | Unichema Chemie Bv | COMPLEXASTERS, COMPOSITIONS CONTAINING SAME AND THEIR USE |
US6235691B1 (en) * | 1997-11-12 | 2001-05-22 | Exxon Chemical Patents Inc. | Oil compositions with synthetic base oils |
JP4049916B2 (en) * | 1998-12-25 | 2008-02-20 | 出光興産株式会社 | High temperature lubricating oil composition |
JP2000273480A (en) * | 1999-03-29 | 2000-10-03 | Asahi Denka Kogyo Kk | Lubricating composition |
US6436881B1 (en) * | 2001-06-01 | 2002-08-20 | Hatco Corporation | High temperature lubricant composition |
US6884861B2 (en) * | 2001-12-10 | 2005-04-26 | The United States Of America As Represented By The Secretary Of The Navy | Metal nanoparticle thermoset and carbon compositions from mixtures of metallocene-aromatic-acetylene compounds |
US20040092411A1 (en) * | 2002-11-13 | 2004-05-13 | Godici Patrick E. | High temperature stability lubricant composition containing short chain acids and method for making the same |
WO2006003992A1 (en) * | 2004-06-30 | 2006-01-12 | The Nisshin Oillio Group, Ltd. | Liquid ester composition and cosmetic preparation containing the same |
-
2007
- 2007-01-30 US US11/699,946 patent/US20070179069A1/en not_active Abandoned
- 2007-01-30 WO PCT/US2007/002632 patent/WO2007089835A2/en active Application Filing
- 2007-01-30 EP EP07762776.8A patent/EP1981955B9/en active Active
Also Published As
Publication number | Publication date |
---|---|
WO2007089835A3 (en) | 2008-02-07 |
US20070179069A1 (en) | 2007-08-02 |
EP1981955B1 (en) | 2013-08-28 |
EP1981955A2 (en) | 2008-10-22 |
WO2007089835A2 (en) | 2007-08-09 |
EP1981955A4 (en) | 2010-09-15 |
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