EP2235147A1 - Marine diesel cylinder lubricants for improved fuel efficiency - Google Patents
Marine diesel cylinder lubricants for improved fuel efficiencyInfo
- Publication number
- EP2235147A1 EP2235147A1 EP08876491A EP08876491A EP2235147A1 EP 2235147 A1 EP2235147 A1 EP 2235147A1 EP 08876491 A EP08876491 A EP 08876491A EP 08876491 A EP08876491 A EP 08876491A EP 2235147 A1 EP2235147 A1 EP 2235147A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition
- oil
- acid
- engine
- lubricating
- 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.)
- Granted
Links
- 239000000314 lubricant Substances 0.000 title claims abstract description 64
- 239000000446 fuel Substances 0.000 title description 19
- 239000000203 mixture Substances 0.000 claims abstract description 117
- 239000003607 modifier Substances 0.000 claims abstract description 37
- 230000001050 lubricating effect Effects 0.000 claims abstract description 22
- 239000005078 molybdenum compound Substances 0.000 claims abstract description 10
- 150000002752 molybdenum compounds Chemical class 0.000 claims abstract description 10
- 239000003599 detergent Substances 0.000 claims description 51
- 150000001412 amines Chemical class 0.000 claims description 38
- 239000002270 dispersing agent Substances 0.000 claims description 30
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 23
- 239000000194 fatty acid Substances 0.000 claims description 23
- 229930195729 fatty acid Natural products 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 23
- 150000004665 fatty acids Chemical class 0.000 claims description 15
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical group CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 claims description 10
- 150000003892 tartrate salts Chemical class 0.000 claims description 10
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 claims description 9
- 239000011575 calcium Substances 0.000 claims description 8
- 229910052791 calcium Inorganic materials 0.000 claims description 8
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 6
- 150000003752 zinc compounds Chemical class 0.000 claims description 5
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 2
- 150000002193 fatty amides Chemical class 0.000 claims description 2
- 238000002485 combustion reaction Methods 0.000 abstract description 5
- -1 polyol ester Chemical class 0.000 description 63
- 239000003921 oil Substances 0.000 description 54
- 235000019198 oils Nutrition 0.000 description 54
- 125000001183 hydrocarbyl group Chemical group 0.000 description 40
- 125000004432 carbon atom Chemical group C* 0.000 description 36
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 30
- 229910052751 metal Inorganic materials 0.000 description 29
- 239000002184 metal Substances 0.000 description 29
- 150000001875 compounds Chemical class 0.000 description 28
- 239000000463 material Substances 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 150000001298 alcohols Chemical class 0.000 description 26
- 239000003795 chemical substances by application Substances 0.000 description 24
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 20
- 239000002253 acid Substances 0.000 description 19
- 150000001336 alkenes Chemical class 0.000 description 17
- 150000002148 esters Chemical class 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 16
- 125000000217 alkyl group Chemical group 0.000 description 15
- 239000010687 lubricating oil Substances 0.000 description 15
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical class OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 13
- 239000000654 additive Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000011975 tartaric acid Substances 0.000 description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 12
- 150000007513 acids Chemical class 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 11
- 235000002906 tartaric acid Nutrition 0.000 description 11
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 10
- 229910052727 yttrium Inorganic materials 0.000 description 10
- 230000002378 acidificating effect Effects 0.000 description 9
- 239000003963 antioxidant agent Substances 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- 229910052796 boron Inorganic materials 0.000 description 8
- 239000003112 inhibitor Substances 0.000 description 8
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 239000011593 sulfur Substances 0.000 description 8
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000003502 gasoline Substances 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 150000002739 metals Chemical class 0.000 description 7
- 150000002924 oxiranes Chemical class 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- 229910052725 zinc Inorganic materials 0.000 description 7
- 239000011701 zinc Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 6
- 238000005260 corrosion Methods 0.000 description 6
- 230000007797 corrosion Effects 0.000 description 6
- 229920000768 polyamine Polymers 0.000 description 6
- 229960001860 salicylate Drugs 0.000 description 6
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 5
- 239000002199 base oil Substances 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 5
- 150000002431 hydrogen Chemical group 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 150000002462 imidazolines Chemical class 0.000 description 5
- 229910052750 molybdenum Inorganic materials 0.000 description 5
- 239000011733 molybdenum Substances 0.000 description 5
- 239000010705 motor oil Substances 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 229920000098 polyolefin Polymers 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 5
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 5
- 229960002317 succinimide Drugs 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
- 239000010689 synthetic lubricating oil Substances 0.000 description 5
- ADOBXTDBFNCOBN-UHFFFAOYSA-N 1-heptadecene Chemical compound CCCCCCCCCCCCCCCC=C ADOBXTDBFNCOBN-UHFFFAOYSA-N 0.000 description 4
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 4
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- 239000004327 boric acid Substances 0.000 description 4
- 150000001639 boron compounds Chemical class 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- VAMFXQBUQXONLZ-UHFFFAOYSA-N icos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 4
- 150000003870 salicylic acids Chemical class 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 150000003460 sulfonic acids Chemical class 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 3
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 3
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
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- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- COTPAMORPWZHKE-UHFFFAOYSA-H trizinc;thiophosphate;thiophosphate Chemical class [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=O.[O-]P([O-])([O-])=S COTPAMORPWZHKE-UHFFFAOYSA-H 0.000 description 1
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- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
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- C10M163/00—Lubricating compositions characterised by the additive being a mixture of a compound of unknown or incompletely defined constitution and a non-macromolecular compound, each of these compounds being essential
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- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
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- C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M129/38—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
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- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/68—Esters
- C10M129/76—Esters containing free hydroxy or carboxyl groups
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- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
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- C10M133/08—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups
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- C10M133/16—Amides; Imides
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- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- C10M2207/28—Esters
- C10M2207/287—Partial esters
- C10M2207/289—Partial esters containing free hydroxy groups
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- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/402—Castor oils
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
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- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/08—Amides
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/28—Amides; Imides
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/046—Overbasedsulfonic acid salts
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- C10M2219/089—Overbased salts
-
- 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
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
-
- 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
- C10N2030/40—Low content or no content compositions
-
- 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
- C10N2040/25—Internal-combustion engines
-
- 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
- C10N2040/25—Internal-combustion engines
- C10N2040/252—Diesel engines
Definitions
- the lubricating composition of the present invention is useful for an internal combustion engine, for example a diesel fueled engine, a gasoline fueled engine, a natural gas fueled engine or a mixed gasoline/alcohol fueled engine.
- the internal combustion engine is a 4-stroke and in
- the lubricant described herein contains an oil of lubricating viscosity.
- the oil of lubricating viscosity may have a SAE grade of SAE 30, SAE 40, SAE 50, or SAE 60.
- the oil of lubricating viscosity may be a SAE 50 oil.
- a SAE 50 oil has a kinematic viscosity of 16.3 mm 2 /s to 21.9 mm 2 /s at 100°C.
- the oil also referred to as a base oil, may be selected from any of the base oils in Groups I-V as specified in the American Petroleum Institute (API) Base Oil Interchangeability Guidelines.
- the five base oil groups are as follows:
- Unrefined, refined and rerefined oils either natural or synthetic (as well as mixtures of two or more of any of these) of the type disclosed herein- above can used in the compositions of the present invention.
- Unrefined oils are those obtained directly from a natural or synthetic source without further purification treatment.
- Refined oils are similar to the unrefined oils except they have been further treated in one or more purification steps to improve one or more properties.
- Rerefined oils are obtained by processes similar to those used to obtain refined oils applied to refined oils which have been already used in
- the lubricant compositions described herein will also contain an organic friction modifier.
- Friction modifiers in general are known to those skilled in the art.
- a useful list of friction modifiers is included in U.S. Pat. No. 4,792,410.
- a list of organic friction modifiers includes:
- fatty phosphites are generally of the formula (RO) 2 PHO.
- An exemplary dialkyl phosphite as shown in the preceding formula, is typically present with a minor amount of monoalkyl phosphite of the formula (RO)(HO)PHO.
- R is conventionally referred to as an alkyl group. It is, of course, possible that the alkyl is actually alkenyl and thus the terms "alkyl” and “alkylated,” as used herein, will embrace other than saturated alkyl groups within the phosphite.
- the phosphite will normally have sufficient hydrocarbyl groups to render the phosphite substantially oleophilic.
- the hydrocarbyl groups may be substantially unbranched.
- Many suitable phosphites are available commercially and may be
- the phosphite may contain 8 to 24 carbon atoms in each of R groups.
- the fatty phosphite may contain 12 to 22 carbon atoms in each of the fatty radicals, or 16 to 20 carbon atoms.
- the fatty phosphite can be formed from oleyl groups, thus having 18 carbon atoms in each fatty radical.
- oil-soluble boron- containing compositions are prepared by reacting, at a temperature from 80°C to 250°C, boric acid or boron trioxide with at least one fatty epoxide having the formula
- R 1 , R 2 , R 3 and R 4 are hydrogen or an aliphatic radical, or any two thereof together with the epoxy carbon atom or atoms to which they are attached, form a cyclic radical.
- the fatty epoxide may contain at least 8 carbon atoms.
- Non-borated fatty epoxides are also useful as friction modifiers.
- Suitable amides include those prepared by condensation with ammonia or with primary or secondary amines such as diethylamine and dietha- nolamine.
- Fatty imidazolines are the cyclic condensation product of an acid with a diamine or polyamine such as a polyethylenepolyamine. The imidazolines are generally represented by the structure
- Metal salts of alkyl salicylates include calcium and other salts of long chain (e.g. Cl 2 to C 16) alkyl-substituted salicylic acids.
- Amine salts of alkylphosphoric acids include salts of oleyl and other long chain esters of phosphoric acid, with amines as described below. Useful amines in this regard are tertiary-aliphatic primary amines, sold under the tradename PrimeneTM.
- R 1 and R 2 are independently linear or branched hydrocarbyl groups. In one embodiment the hydrocarbyl groups are branched. In one embodiment the hydrocarbyl groups are linear.
- the R 1 and R 2 may be incorporated into Formula (I a) and/or (Ib) by either an amine or an alcohol.
- the alcohol includes both monohydric alcohol and polyhydric alcohol. Examples of a suitable branched alcohol include 2-ethylhexanol, isotridecanol, Guerbet alcohols, or mixtures thereof.
- monohydric alcohols examples include methanol, ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol, octadecanol, nonadecanol, eicosanol, or mixtures thereof.
- the monohydric alcohol contains 5 to 20 carbon atoms.
- the alcohol includes either a monohydric alcohol or a polyhydric alcohol.
- esters may be derived from a mixture of all linear alcohols or all branched alcohols, or mixtures of linear and branched alcohols, e.g., mixtures of linear C8-14 alcohols with branched C8 alcohols, or linear C 12- 14 alcohols with branched Cl 3 alcohols or linear C 14- 18 alcohols with branched Cl 8 alcohols, as well as mixtures of Cl 8 with Cl 2 linear alcohols and mixtures of Cl 3 with
- compositions of the present invention may also be free or substantially free from zinc compounds.
- Zinc compounds such as zinc phosphates, zinc thiophosphates (in particular, zinc dialkyl diithiophosphates) and other zinc compounds such as zinc oleates are often used in lubricants as anti- wear or antioxidant agents.
- the lubricants of the present invention may perform well even in the absence of these zinc compounds.
- the amount of zinc in the composition may be 0 to 1000 or 0 to 100, or 1 to 20, or less than 20, or less than 10, or less than 5 parts per million by weight.
- compositions as described herein may also contain a dispers- ant.
- Dispersants are well known in the field of lubricants and include primarily what is known as ashless dispersants and polymeric dispersants. Ashless dispersants are so-called because, as supplied, they do not contain metal and thus do not normally contribute to sulfated ash when added to a lubricant. However they may, of course, interact with ambient metals once they are added to a lubricant which includes metal-containing species. Ashless dispersants are characterized by a polar group attached to a relatively high molecular weight hydrocarbon chain. Typical ashless dispersants include N-substituted long
- the amount of dispersant or borated dispersant (or the combination of the two), if present in the present compositions, may be 0.1 or 0.2 to 5 weight percent, or 0.4 to 4 weight percent, or 0.5 to 3 weight percent, or 0.5 to 1.8 weight percent.
- the overbased materials are prepared by reacting an acidic material (typically an inorganic acid or lower carboxylic acid, such as carbon dioxide) with a mixture comprising an acidic organic compound, a reaction medium comprising at least one inert, organic solvent (e.g., mineral oil, naphtha, toluene, xylene) for said acidic organic material, a stoichiometric excess of a metal base, and a promoter such as a phenol or alcohol and optionally ammonia.
- the acidic organic material will normally have a sufficient number of carbon atoms, for instance, as a hydrocarbyl substituent, to provide a reasonable degree of solubility in oil.
- the amount of excess metal is commonly expressed in terms of metal ratio.
- metal ratio is the ratio of the total equivalents of the metal to the equivalents of the acidic organic compound.
- a neutral metal salt has a metal ratio of one.
- the overall TBN of the composition will be derived from the TBN contribution of the individual components, such as the dispersant, the detergent, and other basic materials.
- the overall TBN for lubricants used as marine diesel cylinder lubricants will typically be greater than 30, e.g., 31 to 100 or 35 to80 or 40 to 70.
- Other lubricants may have an overall TBN of at least 7 or at least 10, or sometimes even at least 20.
- the majority of the TBN is typically contributed by the overbased detergent component.
- the metal compounds useful in making the basic metal salts are generally any Group 1 or Group 2 metal compounds (CAS version of the Periodic Table of the Elements).
- the Group 1 metals of the metal compound include Group Ia alkali metals such as sodium, potassium, and lithium, as well as Group Ib metals such as copper.
- the Group 2 metals of the metal base include the Group 2a alkaline earth metals such as magnesium, calcium, and barium, as well as the Group 2b metals such as zinc or cadmium. [0069] Such overbased materials are well known to those skilled in the art.
- Patents describing techniques for making basic salts of sulfonic acids, carbox- ylic acids, (hydrocarbyl-substituted) phenols, phosphonic acids, and mixtures of any two or more of these include U.S. Patents 2,501 ,731 ; 2,616,905; 2,616,91 1 ;
- the lubricants of the present invention can contain an overbased sulfonate detergent.
- Suitable sulfonic acids include sulfonic and thiosulfonic acids.
- Sulfonic acids include the mono- or polynuclear aromatic or cycloaliphatic sulfonic acid compounds.
- Oil-soluble sulfonates may be represented by one of the following formulas: R 2 -T-(SO 3 -) a and R 3 -(SO 3 -)b, where T is a cyclic nucleus such as typically benzene; R 2 is an aliphatic group such as alkyl, alkenyl, alkoxy, or alkoxyalkyl; (R 2 )-T typically contains a total of at least 15 carbon atoms; and R 3 is an aliphatic hydrocarbyl group typically containing at least 15 carbon atoms. Examples of R 3 are alkyl, alkenyl, alkoxyalkyl, and carboalkoxyalkyl groups.
- Another overbased material which can be present is an overbased phenate detergent.
- the phenols useful in making phenate detergents can be represented by the formula (Ri) a -Ar-(OH) b , wherein R) is an aliphatic hydrocarbyl group of 4 to 400 carbon atoms, or 6 to 80 or 6 to 30 or 8 to 25 or 8 to 15 carbon atoms; Ar is an aromatic group (which can be a benzene group or another aromatic group such as naphthalene); a and b are independently numbers of at least one, the sum of a and b being up to the number of displaceable hydrogens on the aromatic nucleus or nuclei of Ar.
- a and b are independently to 4, or 1 to 2.
- Ri and a are typically such that there is an average of at least 8 aliphatic carbon atoms provided by the Ri groups for each phenol compound. Phenate detergents are also sometimes provided as sulfur- bridged species.
- X comprises -CHO or -CH 2 OH
- Y comprises -CH 2 - or -CH 2 OCH 2 -
- -CHO groups typically comprise at least 10 mole percent of the X and Y groups
- M is hydrogen, ammonium, or a valence of a metal ion
- R 1 is a hydrocarbyl group containing 1 to 60 carbon atoms
- m is 0 to typically 10
- each p is independently 0, 1 , 2, or 3, provided that at least one aromatic ring contains an R 1 substituent and that the total number of carbon atoms in all R 1 groups is at least 7.
- m is 1 or greater, one of the X groups can be hydrogen.
- the expression "represented by the formula” indicates that the formula presented is generally representative of the structure of the chemical in question. However, it is well known that minor variations can occur, including in particular positional isomerization, that is, location of the X, Y, and R groups at different position on the aromatic ring from those shown in the structure. The expression “represented by the formula” is expressly intended to encompass such variations.
- a formaldehyde equivalent e.g., paraform, formalin.
- Salixarate derivatives and methods of their preparation are described in greater detail in U.S. patent number 6,200,936 and PCT Publication WO 01/56968. It is believed that the salixarate derivatives have a predominantly linear, rather than macrocyclic, structure, although both structures are intended to be encompassed by the term "salixarate.”
- Glyoxylate detergents are similar overbased materials which are based on an anionic group which, in one embodiment, may have the structure
- each R is independently an alkyl group containing at least 4, and preferably at least 8 carbon atoms, provided that the total number of carbon atoms in all such R groups is at least 12, preferably at least 16 or 24.
- each R can be an olefin polymer substituent.
- the acidic material upon from which the overbased glyoxylate detergent is prepared is the condensation product of a hydroxyaromatic material such as a hydrocarbyl-substituted phenol with a carboxylic reactant such as glyoxylic acid and other omega-oxoalkanoic acids.
- a hydroxyaromatic material such as a hydrocarbyl-substituted phenol
- carboxylic reactant such as glyoxylic acid and other omega-oxoalkanoic acids.
- the salicylic acids may thus be hydrocarbyl- substituted salicylic acids, such as aliphatic hydrocarbon-substituted salicylic acids wherein each substituent contains an average of at least 8 carbon atoms per substituent and 1 to 3 substituents per molecule.
- the substituents can be polyalkene substituents, where polyalkenes include homopolymers and inter- polymers of polymerizable olefin monomers of 2 to 16, or 2 to 6, or 2 to 4 carbon atoms.
- the olefins may be monoolefins such as ethylene, propylene, 1 -butene, isobutene, and 1 -octene; or a polyolefinic monomer, such as diolef ⁇ nic monomer, such 1 ,3-butadiene and isoprene.
- the hydrocar- byl substituent group or groups on the salicylic acid contains 7 to 300 carbon atoms and can be an alkyl group having a molecular weight of 150 to 2000.
- the polyalkenes and polyalkyl groups are prepared by conventional procedures, and substitution of such groups onto salicylic acid can be effected by known meth-
- the detergent component may also be a mixture of detergents or so-called “hybrid detergents,” also referred to as complex detergents or mixed substrate detergents.
- the hybrid may be an overbased phenate-salicylate detergent. Methods of preparing overbased phenate- salicylate detergents are disclosed in EP 123 6791 Al and EP 123 6792 Al .
- the hybrid may be prepared by reacting, in the presence of a suspension and acidifying overbasing agent, an alkyl aromatic sulfonic acid and at least one alkyl phenol (such as alkyl phenol, aldehyde-coupled alkyl phenol, sulfurized alkyl phenol) and optionally alkyl salicylic acid. Preparation of such materials is also disclosed in WO97046643
- the present lubricants may thus contain up to 20 percent by weight, (or 0.1 to 19 or 0.5 to 18 or 1 tol 7 or 0.1 to 10 or 0.5 to 7 or 1 to 5 percent by weight) of an overbased calcium alkylphenol sulfide detergent (of any of a number of degrees of overbasing, high or low TBN) or up to 20 percent by weight (or 0.1 to 17.5 or 0.1 to 17 or 0.5 to 15 or 1 to 17 or 0.5 to 15 or 2 to 12 or 6 to 10 percent by weight) of a relatively highly overbased linear alkyl sulfonate detergent, that is, having an oil-free TBN of 400-900, or mixtures of such materials.
- an overbased calcium alkylphenol sulfide detergent of any of a number of degrees of overbasing, high or low TBN
- a relatively highly overbased linear alkyl sulfonate detergent that is, having an oil-free TBN of 400-900, or mixtures of such materials.
- the total amount of the overbased detergents, in the formulations of the present invention is typically at least 0.6 weight percent on an oil- free basis. In other embodiments, it can be present in amounts of 0.7 to 20 weight percent or 1 to 18 weight percent or 3 to 13 weight percent.
- the detergent component consists of a salicylate detergent (and no sulfonate). In another embodiment the detergent component consists of a sulfonate detergent (and no phenate).
- Viscosity modifiers include hydrogenated copolymers of styrene and butadiene, ethylene-propylene copolymers, polyisobutenes, hydrogenated styrene-isoprene polymers, hydrogenated isoprene polymers, polymethacrylates, polyacrylates, polyalkyl styrenes, hydrogenated alkenyl aryl conjugated diene copolymers, polyolefins, esters of maleic anhydride olefin copolymers, and esters of maleic anhydride-styrene copolymers.
- the borate esters or borate alcohols may be substantially the same except the borate alcohol has at least one hydroxyl group that is not esterified. Therefore, as used herein the term "borate ester" is used to refer to either borate ester or borate alcohol.
- the borate esters or borate alcohols may have a formula B(OR') 3 or be a derivative thereof containing a >B-O-B ⁇ group, wherein R' may be hydrogen or a hydrocarbyl group, typically containing 1 to 40, or 1 to 20 carbon atoms on each R'.
- R' When R' is hydrogen, the boron-containing compound is a borate alcohol.
- R' is hydrocarbyl, the boron-containing compound is a borate ester.
- the borate ester may be prepared by the reaction of a
- boron compound such as boric acid, boron oxides, or boron halides, and at least one compound selected from epoxy compounds, halohydrin compounds, epihalohydrin compounds, alcohols and mixtures thereof.
- the alcohols include dihydric alcohols, trihydric alcohols or higher alcohols, with the proviso for one embodiment that hydroxyl groups are on adjacent, i.e., vicinal, carbon atoms.
- Some of the boron- containing compounds may also sere as friction modifiers, as described above.
- Dithiocarbamate-containing compounds may be prepared by reacting a dithiocarbamate acid or salt with an unsaturated compound.
- Suitable olefins that may be sulfurized to form sul- furized olefins include propylene, butylene, isobutylene, pentene, hexane, heptene, octane, nonene, decene, undecene, dodecene, undecyl, tridecene, tetradecene, pentadecene, hexadecene, heptadecene, octadecene, octadecenene, nonodecene, eicosene or mixtures thereof.
- Extreme Pressure (EP) agents include sulfur- and chlorosulfur- containing EP agents, chlorinated hydrocarbon EP agents and phosphorus EP agents.
- EP agents include chlorinated wax; organic sulfides and polysulfides such as dibenzyldisulfide, bis-(chlorobenzyl) disulfide, dibutyl tetrasulf ⁇ de, sulfurized methyl ester of oleic acid, sulfurized alkylphenol, sulfurized dipentene, sulfurized terpene, and sulfurized Diels-Alder adducts; phosphosulfurized hydrocarbons such as the reaction product of phosphorus sulfide with turpentine or methyl oleate; phosphorus esters such as the dihydro- carbon and trihydrocarbon phosphites, e.g., dibutyl phosphite, diheptyl phosphite, dicyclohexyl phosphit
- Metal deactivators include derivatives of benzotriazoles (typically tolyltriazole), dimercaptothiadiazole derivatives, 1 ,2,4-triazoles, benzimida- zoles, 2-alkyldithiobenzimidazoles, or 2-alkyldithiobenzothiazoles.
- Foam inhibitors include copolymers of ethyl acrylate and 2-ethylhexylacrylate and optionally vinyl acetate.
- Demulsifiers include trialkyl phosphates, polyethylene glycols, polyethylene oxides, polypropylene oxides and (ethylene oxide- propylene oxide) polymers.
- Pour point depressants include esters of maleic anhydride-styrene, polymethacrylates, polyacrylates or polyacrylamides.
- the presently described lubricants may also contain titanium- containing additives such as titanium alkoxides or titanium-modified dispers- ants, as described in greater detail in, e.g., U.S. Application 2006-0217271.
- hydrocarbyl substituent or “hydrocarbyl group” is used in its ordinary sense, which is well-known to those skilled in the art. Specifically, it refers to a group having a carbon atom directly attached to the remainder of the molecule and having predominantly hydrocarbon character.
- hydrocarbyl groups include: hydrocarbon substituents, that is, aliphatic (e.g., alkyl or alkenyl), ali- cyclic (e.g., cycloalkyl, cycloalkenyl) substituents, and aromatic-, aliphatic-, and alicyclic-substituted aromatic substituents, as well as cyclic substituents wherein the ring is completed through another portion of the molecule (e.g., two substituents together form a ring); substituted hydrocarbon substituents, that is, substituents containing non- hydrocarbon groups which, in the context of this invention, do not alter the predominantly hydrocarbon nature of the substituent (e.g., halo (especially
- hetero substituents that is, substituents which, while having a predominantly hydrocarbon character, in the context of this invention, contain atoms other than carbon in a ring or chain otherwise composed of carbon atoms. Heteroatoms include sulfur, oxygen, nitrogen, and encompass substituents as pyridyl, furyl, thienyl and imidazolyl. In general, no more than two, or no more than one, non-hydrocarbon substituent will be present for every ten carbon atoms in the hydrocarbyl group; typically, there will be no non-hydrocarbon substituents in the hydrocarbyl group.
- a "good" baseline lubricant formulation is prepared characteristic of a marine diesel cylinder lubricant.
- the lubricant contains, in an API Group I mineral oil:
- Example 1 The formulation of Example 6, containing glycerol monooleate, is repeated, except that the borated succinimide dispersant is replaced by an equal amount of a corresponding non-borated succinimide dispersant. The same friction test described above is performed, with the results shown below:
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Abstract
Description
Claims
Applications Claiming Priority (2)
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US1304307P | 2007-12-12 | 2007-12-12 | |
PCT/US2008/085617 WO2010016856A1 (en) | 2007-12-12 | 2008-12-05 | Marine diesel cylinder lubricants for improved fuel efficiency |
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EP2235147A1 true EP2235147A1 (en) | 2010-10-06 |
EP2235147B1 EP2235147B1 (en) | 2019-02-20 |
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FR2951456B1 (en) * | 2009-10-16 | 2011-12-09 | Total Raffinage Marketing | ENGINE LUBRICANT |
CN103492536A (en) * | 2011-02-01 | 2014-01-01 | 钱德拉谢卡尔·H·乔希 | Production of hydrocarbon fuels from plant oil and animal fat |
FR2974111B1 (en) * | 2011-04-14 | 2013-05-10 | Total Raffinage Marketing | LUBRICANT CYLINDER FOR MARINE ENGINE TWO TIMES |
JP5922454B2 (en) | 2012-03-21 | 2016-05-24 | 出光興産株式会社 | Lubricating oil additive composition and lubricating oil composition |
FR3002947B1 (en) * | 2013-03-06 | 2016-03-25 | Total Raffinage Marketing | LUBRICATING COMPOSITION FOR MARINE ENGINE |
CN105339476A (en) * | 2013-05-30 | 2016-02-17 | 路博润公司 | Synergistic additive combination for industrial gear oils |
FR3027607B1 (en) * | 2014-10-27 | 2018-01-05 | Total Marketing Services | LUBRICANT FOR MARINE ENGINE |
JP6789994B2 (en) * | 2015-06-12 | 2020-11-25 | ザ ルブリゾル コーポレイションThe Lubrizol Corporation | Michael-added amino ester as a total base value booster for marine diesel engine lubrication compositions |
SG11202004886WA (en) * | 2017-12-04 | 2020-06-29 | Lubrizol Corp | Alkylphenol detergents |
CN111454763B (en) * | 2020-04-14 | 2022-04-29 | 福建黑狮润滑油有限公司 | Fully-synthetic staged marine internal combustion engine lubricating oil and preparation method thereof |
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- 2008-12-05 EP EP08876491.5A patent/EP2235147B1/en active Active
- 2008-12-05 WO PCT/US2008/085617 patent/WO2010016856A1/en active Application Filing
- 2008-12-05 US US12/744,698 patent/US20110030648A1/en not_active Abandoned
- 2008-12-05 CA CA2708333A patent/CA2708333A1/en not_active Abandoned
Non-Patent Citations (1)
Title |
---|
See references of WO2010016856A1 * |
Also Published As
Publication number | Publication date |
---|---|
EP2235147B1 (en) | 2019-02-20 |
US20110030648A1 (en) | 2011-02-10 |
WO2010016856A1 (en) | 2010-02-11 |
CA2708333A1 (en) | 2010-02-11 |
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