JP5406931B2 - Lubricant basestock usage - Google Patents
Lubricant basestock usage Download PDFInfo
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- JP5406931B2 JP5406931B2 JP2011534427A JP2011534427A JP5406931B2 JP 5406931 B2 JP5406931 B2 JP 5406931B2 JP 2011534427 A JP2011534427 A JP 2011534427A JP 2011534427 A JP2011534427 A JP 2011534427A JP 5406931 B2 JP5406931 B2 JP 5406931B2
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- engine
- ester
- lubricant
- propanediol
- acid
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- 239000000314 lubricant Substances 0.000 title claims description 42
- 150000002148 esters Chemical class 0.000 claims description 34
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 16
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 16
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 10
- RXGPYPPCEXISOV-UHFFFAOYSA-N 2-propylheptanoic acid Chemical compound CCCCCC(C(O)=O)CCC RXGPYPPCEXISOV-UHFFFAOYSA-N 0.000 claims description 9
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 7
- 150000005691 triesters Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- SZSSMFVYZRQGIM-UHFFFAOYSA-N 2-(hydroxymethyl)-2-propylpropane-1,3-diol Chemical compound CCCC(CO)(CO)CO SZSSMFVYZRQGIM-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 3
- 238000002485 combustion reaction Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 13
- 229940035437 1,3-propanediol Drugs 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 150000001735 carboxylic acids Chemical class 0.000 description 10
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical class C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 7
- 239000000539 dimer Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000013638 trimer Substances 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 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 description 4
- 238000002156 mixing Methods 0.000 description 4
- 241000894007 species Species 0.000 description 4
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 3
- 241001550224 Apha Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000002199 base oil Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- -1 ester compounds Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 229920013639 polyalphaolefin Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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
- C10M105/34—Esters of monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
- C10M2207/2835—Esters of polyhydroxy compounds 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
- C10M2209/1095—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified used as base material
-
- 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
- C10N2020/011—Cloud point
-
- 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
-
- 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
-
- 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
- C10N2030/02—Pour-point; Viscosity index
-
- 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
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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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
- C10N2040/13—Aircraft turbines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- 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
-
- 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
- C10N2040/255—Gasoline engines
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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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
- C10N2040/26—Two-strokes or two-cycle engines
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は、自動車、航空機、船舶、固定(定置)のエンジンまたはタービン用の潤滑剤(潤滑油)ベースストック(基油)に関する。その潤滑剤ベースストック(基油)は、2−プロピルヘプタン酸と、少なくとも1種の2,2−置換1,3プロパンジオールおよび/またはその少なくとも1種の二量体、三量体またはポリマー、および/または前記2,2−置換1,3プロパンジオールまたはその前記二量体、三量体またはポリマーの少なくとも1種のアルコキシル化された種との間の少なくとも1種のエステルを含んでいる。別の側面(観点)では、本発明は、潤滑剤の製造または生成における前記潤滑剤ベースストックの使用(使用法)に関する。 The present invention relates to a lubricant (lubricant) base stock (base oil) for automobiles, aircraft, ships, fixed (stationary) engines or turbines. The lubricant base stock (base oil) comprises 2-propylheptanoic acid and at least one 2,2-substituted 1,3-propanediol and / or at least one dimer, trimer or polymer thereof, And / or at least one ester between the 2,2-substituted 1,3 propanediol or at least one alkoxylated species of the dimer, trimer or polymer thereof. In another aspect (viewpoint), the present invention relates to the use (use) of said lubricant base stock in the manufacture or production of a lubricant.
特定の適用例(アプリケーション)に適合するものとして、適切な性能の添加剤を配合した潤滑剤ベースストックは、特定の適用例の各要求(要件)に完全に適合し(従わ)なければならず、典型的には、例えば粘度のような1つの特定のパラメータのみに適合するだけでは充分でなく、適用例の複数の特性の組(set)全体に対する適合性が要求され、その組は、しばしば、例えば粘度、粘度安定性、引火点(flash point)、流動点(pour point)、揮発度(volatility)、等のような複数のパラメータに対する複数の特定の要求を含んでいる。 Lubricant base stocks formulated with appropriate performance additives to suit a particular application (application) must fully meet (follow) each requirement (requirement) of the particular application. Typically, it is not sufficient to fit only one particular parameter, such as viscosity, for example, but suitability for the entire set of properties of the application is required, and that set is often Including specific requirements for multiple parameters such as viscosity, viscosity stability, flash point, pour point, volatility, etc.
各潤滑剤ベースストックは、API(American Petroleum Institute, API Publication 1509)に従って、それらの化学的組成に従った5つのカテゴリに分類される。グループI〜IIIは、鉱油ベースストック(mineral oil base stocks)の相異なる等級(grades)からなり、グループIVは、ポリ(α−オレフィン)について定義され、グループVは、エステルベースストックを含む(含めて)その他の全てのベースストックのために留保(確保)されている。この技術分野において、様々な異なるグループ(群)のベースストックが或る典型的な潤滑剤性能(例えば、低温度特性、酸化安定性、および/または相溶性(compatibility、共溶性、混和性)特性のような潤滑剤性能)に寄与することが知られている。また、この技術分野において、特定の適用例に対する最終製品の潤滑剤製品を配合する(formulate)とき、1つまたはそれ以上のグループの2つまたはそれ以上のベースストックを組み合わせることができること、が知られている。合成エステルは、米国特許第5151205号に開示されたAPIグループIVのポリ(α−オレフィン)のような他のグループのベースストックと組み合わせること、または米国特許第5665683号に開示されたAPIグループ1〜3の鉱油と組み合わせること、が知られている。 Each lubricant base stock is classified into five categories according to their chemical composition according to the API (American Petroleum Institute, API Publication 1509). Groups I-III consist of different grades of mineral oil base stocks, Group IV is defined for poly (α-olefins), and Group V includes ester base stocks (included) B) reserved for all other base stocks. In this technical field, various different groups of basestocks have certain typical lubricant performance (eg, low temperature properties, oxidative stability, and / or compatibility properties). It is known that it contributes to lubricant performance). It is also known in the art that two or more base stocks in one or more groups can be combined when formulating the final lubricant product for a particular application. It has been. Synthetic esters can be combined with other groups of base stocks such as API group IV poly (α-olefins) disclosed in US Pat. No. 5,151,205, or API groups 1 to 1 disclosed in US Pat. No. 5,665,683. It is known to combine with 3 mineral oils.
潤滑剤は、典型的には、適切な固有の特性(inherent properties、内部特性、内在特性)の潤滑剤ベースストックと、または、それぞれの適切な固有の特性の複数の潤滑剤ベースストックの混合物と、添加剤および任意にその他の配合助剤との組合せで配合される。ジオール、トリオール、テトロールおよびポリオールのエステルは、しばしば使用される、多数の高性能潤滑剤適用例における潤滑剤ベースストックである。それらのエステルは、2つ以上のヒドロキシル基を有するアルコールからそのアルコールをカルボン酸または酸混合物でエステル化することによって得られる。そのエステル化プロセス(工程)において、そのアルコールのヒドロキシル基は、それらに酸成分を付加することによって、部分的にまたは全て(完全に)、エステル基に転換(変換)される。 A lubricant is typically a lubricant base stock with appropriate inherent properties, or a mixture of multiple lubricant base stocks with appropriate proper properties. , In combination with additives and optionally other blending aids. Esters of diols, triols, tetrols and polyols are lubricant basestocks in many high performance lubricant applications that are often used. These esters are obtained from an ester having two or more hydroxyl groups by esterifying the alcohol with a carboxylic acid or acid mixture. In the esterification process (step), the hydroxyl groups of the alcohol are converted (converted) into ester groups, either partially or completely (completely) by adding an acid component thereto.
特定の最終的または目的の特性(end properties)を満たす潤滑剤の配合は、典型的には、要求される複数の特性に近い複数の特性を本質的に(inherently、内在的に)示すベースストックを選択するステップ(工程)を含んでいる(伴う、必要とする)。この技術分野において、所望の特性の最終的な微細な調整は、ベースストックを、仕様およびそれらの他の各要求に従ってその特性を修正(調製)することができるその他の成分と混合することによって、行えることが、知られている。しかし、混合は、常に好ましいとは限らない。その理由は、それによってその系(システム)に、その潤滑剤に含まれる少なくとも増大された数の成分の形態で複雑さ(complexity)が導入されるからである。 Lubricant formulations that meet certain final or end properties typically have base stocks that exhibit inherent properties that are close to the required properties. Includes (accommodates, requires) a step. In this technical field, the final fine adjustment of the desired properties is achieved by mixing the base stock with other ingredients that can modify (prepare) their properties according to the specifications and their respective requirements. It is known that it can be done. However, mixing is not always preferred. The reason is that it introduces complexity into the system in the form of at least an increased number of components contained in the lubricant.
さらに、この技術分野において、複数の或るエステル特性は、各単一の(single、均一な、均質な)反応体の代わりに複数の開始材料の各混合物を選択することによって強い影響を受け得る(受ける可能性がある)ことが、知られている。そのエステル生成物は、例えば、カルボン酸でエステル化された前記アルコールの混合物からなるものであってもよく、または前記アルコールは複数種のカルボン酸の混合物でエステル化することもでき、それによって例えば改善された相溶性(compatibility)および低温流動(cold-flow、低温流れ)特性が得られる。さらに、一般論としても、これは、前記アルコールの混合物を複数のカルボン酸の混合物と組み合わせるときにも適用し得るものであり、それによってエステルの最終生成物(end-products)の統計的な混合状態(混合物)が得られるようになる。しかし、原材料の前記混合物を基材(基剤)とする各種のエステルは、全ての事例において望ましいわけではない。それら(エステル)は、その系(システム)に対して或る度合いの組成の不確実性を生じさせ(誘導し)、統計的に形成されるエステル化合物の中の1種またはそれ以上のものは、不所望なおよび/または不利な(adverse)性能の一因となり得る(に寄与し得る、に寄与する可能性がある)。従って、有利な内部特性(固有の特性)を示す様々な異なる基本的に(本質的に)単一の(均一な、均質な)反応物のエステルの範囲に対するニーズ(必要性)および要求が存在する。 Furthermore, in this technical field, certain ester properties can be strongly influenced by selecting each mixture of multiple starting materials instead of each single, homogeneous, reactant. It is known that (possibly). The ester product may consist, for example, of a mixture of the alcohols esterified with a carboxylic acid, or the alcohol may be esterified with a mixture of carboxylic acids, for example Improved compatibility and cold-flow properties are obtained. Furthermore, in general terms, this is also applicable when combining a mixture of the alcohols with a mixture of carboxylic acids, thereby statistically mixing the end-products of the ester. A state (mixture) is obtained. However, various esters based on the aforementioned mixture of raw materials (base) are not desirable in all cases. They (esters) cause some degree of compositional uncertainty to the system, and one or more of the statistically formed ester compounds are May contribute to (and may contribute to) undesirable and / or adverse performance. Thus, there is a need (need) and requirement for a range of different fundamentally (essentially) single (homogeneous, homogeneous) reactant esters that exhibit advantageous internal properties (inherent properties). To do.
流動点は潤滑剤の特性であり、その特性は潤滑剤の低温流動特性の特徴を表す(を特徴づける)。流動点は、テスト潤滑剤が定められた度合いの流動性(fluidity)を示す最低の温度の読み取り(値)として報告される。より詳細な説明が、標準ASTM D5950で行われている。低い流動点は、例えば、寒冷気候および/または冬期の状態(条件)においてエンジンの始動において生じる低い温度状態で使用することを目的とする潤滑剤において望ましい。良好な低温特性を必要とする適用例(アプリケーション)の例には、自動車および航空機(aviation)用の潤滑剤(油)、自動車、固定および2ストローク(サイクル、行程)のエンジン用の潤滑剤、圧媒液(hydraulic fluids、作動液、圧媒油、作動油、油圧油)、冷凍(refrigeration、冷却)潤滑剤、絶縁油(dielectric fluids、絶縁流体)およびグリース(潤滑油)が含まれるが、これらに限定されない。 The pour point is a characteristic of the lubricant, which characterizes (characterizes) the low temperature flow characteristics of the lubricant. The pour point is reported as the lowest temperature reading (value) at which the test lubricant exhibits a defined degree of fluidity. A more detailed description is given in standard ASTM D5950. A low pour point is desirable, for example, in lubricants intended to be used at low temperature conditions that occur at engine start-up in cold weather and / or winter conditions (conditions). Examples of applications (applications) that require good low temperature properties include lubricants (oil) for automobiles and aviation, lubricants for automobiles, fixed and two-stroke (cycle, stroke) engines, Includes hydraulic fluids, hydraulic fluids, hydraulic fluids, hydraulic fluids, refrigeration lubricants, insulating fluids and greases. It is not limited to these.
分岐(branched、枝分かれ、分枝)カルボン酸のエステルは、例えば米国特許第4514314号に開示されているように、流動点の減少(低下)に寄与することが知られている。しかし、現時点では、報告され使用された分岐カルボン酸は、ネオ(neo-)分岐またはイソ(iso-)分岐のいずれかである。2−エチルヘキサン酸は、4より多い炭素を有する唯一の使用される2−分岐カルボン酸であり、文献に開示された10以上の炭素原子を有するカルボン酸は、直鎖(linear)酸、イソ−酸、またはネオ−酸のいずれかである。 It is known that esters of branched carboxylic acids contribute to the reduction (decrease) of the pour point, as disclosed, for example, in US Pat. No. 4,514,314. However, at present, the branched carboxylic acids reported and used are either neo- or iso-branches. 2-Ethylhexanoic acid is the only 2-branched carboxylic acid used having more than 4 carbons, and carboxylic acids having 10 or more carbon atoms disclosed in the literature are linear acids, iso Either an acid or a neo-acid.
発明の概要
次いで、まったく驚くことには、潤滑剤ベースストックとして意図されたエステル中の酸成分として2−プロピルヘプタン酸(2-propylheptanoic acid)を導入すると、そのエステルの流動点がかなり(大幅に、有意に)低下することが、発見された。本発明によれば、高い引火点(flash point)、少ない(低い)蒸発損失(low evaporation loss)、高い粘度(viscosity、粘性)、予期されない例外的な低い流動点、および高い粘度指数の値(high viscosity index value)の得られた組合せは、現在知られている潤滑剤の特性を調節する場合における新しい技術的機会(opportunity、条件、状況)を示唆している。開始物質(材料)として、この技術分野において周知の2−エチルヘキサン酸とは別に(以外には)、2−分岐カルボン酸も、また、そのエステルの分子量とその潤滑剤の流動点の間のいかなる相関性(相関関係)も、エステル潤滑剤および/または潤滑剤ベースストックについて、報告されたことはない。
Summary of the Invention Then, quite surprisingly, when 2-propylheptanoic acid is introduced as the acid component in the ester intended as a lubricant base stock, the pour point of the ester is significantly (significantly greater). , Significantly) was found to decrease. According to the present invention, high flash point, low (low) evaporation loss, high viscosity (viscosity), unexpected exceptional low pour point, and high viscosity index values ( The resulting combination of high viscosity index values suggests new technical opportunities (opportunity, conditions, circumstances) in adjusting the properties of currently known lubricants. As starting material (material), apart from (other than) 2-ethylhexanoic acid well known in the art, a 2-branched carboxylic acid can also be used between the molecular weight of the ester and the pour point of the lubricant. No correlation (correlation) has been reported for ester lubricants and / or lubricant base stocks.
従って、本発明は、2−プロピルヘプタン酸(2-propylheptanoic acid)と、少なくとも1種の2,2−置換1,3プロパンジオール(at least one 2,2-substituted 1,3-propanediol)および/またはその少なくとも1種の二量体、三量体またはポリマー(at least one dimer, trimer or polymer thereof)、および/または前記2,2−置換1,3プロパンジオールまたはその前記二量体、三量体またはポリマーの少なくとも1種のアルコキシル化された種(at least one alkoxylated species of a said 2,2-substituted 1,3-propanediol or a said dimer, trimer or polymer thereof)との間の少なくとも1種のエステルを含む、自動車、航空機、船舶、または固定エンジンまたはタービンの潤滑剤ベースストックに関する。 Accordingly, the present invention relates to 2-propylheptanoic acid and at least one 2,2-substituted 1,3-propanediol and / or Or at least one dimer, trimer or polymer thereof, and / or the 2,2-substituted 1,3-propanediol or the dimer, trimer thereof At least one alkoxylated species of the body or polymer at least one of the alkoxylated species of a said 2,2-substituted 1,3-propanediol or a said dimer, trimer or polymer The present invention relates to lubricant, base stocks for automobiles, aircraft, ships, or stationary engines or turbines containing esters.
前記2,2−置換1,3プロパンジオールは、本発明の好ましい実施形態において、2,2−ジアルキル−1,3−プロパンジオール(2,2-dialkyl-1,3-propanediol)、2−アルキル−2−ヒドロキシアルキル−1,3プロパンジオール(2-alkyl-2-hydroxyalkyl-1,3-propanediol)または2,2−ジヒドロキシアルキル−1,3プロパンジオール(2,2-dihydroxyalkyl-l,3-propanediol)であり、ここで前記アルキルは、好ましくはC1−C8アルキル(C1-C8 alkyl)である。 前記2,2置換1,3−プロパンジオール(2,2-substituted 1,3-propanediol)およびその前記二量体、三量体およびポリマー(dimer, trimer and polymer thereof)の最も好ましい実施形態には、ネオペンチルグリコール(neopentyl glycol)、2−ブチル−2−エチル−1,3−プロパンジオール(2-butyl-2-ethyl-1,3-propanediol)、トリメチロールエタン(trimethylolethane)、トリメチロールブタン(trimethylolbutane)、トリメチロールプロパン(trimethylolpropane)、ペンタエリスリトール(pentaerythritol)、ジ−トリメチロールプロパン(di-trimethylolpropane)およびジ−ペンタエリスリトール(di-pentaerythritol)が含まれる(挙げられる)。 前記アルコキシル化された種(alkoxylated species)は、好ましくは、エトキシ化および/またはプロポキシ化された(ethoxylated and/or propoxylated)トリメチロールエタン(trimethylolethane)、トリメチロールプロパン(trimethylolpropane)、トリメチロールブタン(trimethylolbutane)、ペンタエリスリトール(pentaerythritol)、ジ−トリメチロールプロパン(di-trimethylolpropane)およびジ−ペンタエリスリトール(di-pentaerythritol)からなる群から選択される。 In a preferred embodiment of the present invention, the 2,2-substituted 1,3-propanediol is 2,2-dialkyl-1,3-propanediol, 2-alkyl. 2-hydroxy-2-hydroxyalkyl-1,3-propanediol or 2,2-dihydroxyalkyl-1,3-propanediol a propanediol), wherein the alkyl is preferably C 1 -C 8 alkyl (C 1 -C 8 alkyl). The most preferred embodiment of the 2,2-substituted 1,3-propanediol and its dimer, trimer and polymer antagonists are: , Neopentyl glycol, 2-butyl-2-ethyl-1,3-propanediol, trimethylolethane, trimethylolbutane ( trimethylolbutane, trimethylolpropane, pentaerythritol, di-trimethylolpropane and di-pentaerythritol are included (included). Said alkoxylated species are preferably ethoxylated and / or propoxylated trimethylolethane, trimethylolpropane, trimethylolbutane. ), Pentaerythritol, di-trimethylolpropane and di-pentaerythritol.
前記エステルは、本発明の特に好ましい実施形態において、前記2−アルキル−2―ヒドロキシアルキル−1,3−プロパンジオール(2-alkyl-2-hydroxyalkyl-1,3-propanediol)または前記2,2−ジヒドロキシアルキル−1,3−プロパンジオール (2,2-dihydroxyalkyl-l,3-propanediol)、または、その前記二量体(dimer)、三量体(trimer)またはポリマー、のトリエステル(triester)またはテトラエステル(tetraester)、例えば、2−プロピルヘプタン酸(2-propylheptanoic acid)と、ペンタエリスリトール(pentaerythritol)、トリメチロールプロパン(trimethylolpropane)またはジ−トリメチロールプロパン(di-trimethylolpropane)との間のエステル化生成物(esterification product)であり、それは、少なくとも95重量%(例えば、少なくとも97重量%)のトリエステル(triester)またはテトラエステル(tetraster)含有量(content)を有するものである。 In a particularly preferred embodiment of the present invention, the ester is the 2-alkyl-2-hydroxyalkyl-1,3-propanediol or the 2,2- 2,2-dihydroxyalkyl-1,3-propanediol, or a triester of said dimer, trimer or polymer, or Esterification between tetraesters, for example, 2-propylheptanoic acid and pentaerythritol, trimethylolpropane or di-trimethylolpropane An esterification product, which is at least 95% (eg, at least 97% by weight) triester ter) or tetraster content.
別の観点では、本発明は、例えば自動車(automotive)エンジン、航空機(aeronautic)エンジン、船舶(marine)エンジンおよび固定(stationary、定置)エンジン(engine、機関)のような内燃エンジン(内燃機関)およびタービン・エンジン用の潤滑剤の製造における上述した潤滑剤ベースストックの使用に関する。前記エンジンは、例えば、2ストローク・エンジン(2サイクル・エンジン、2行程エンジン)を含む、オットー(otto)エンジン、ディーゼル(diesel)エンジン、ヴァンケル(wanckel、ロータリ)エンジン、およびジェット(jet)エンジンによって適切に例示することができる(suitably be exemplified by)。ここで最も好ましい潤滑剤ベースストックは、トリメチロールプロパン(trimethylolpropane)のトリエステル(triester)、またはペンタエリスリトール(pentaerythritol)および/またはジ−トリメチロールプロパン(di-trimethylolpropane)のテトラエステルを含んでいる。 In another aspect, the invention relates to internal combustion engines, such as, for example, automotive engines, aeronautic engines, marine engines and stationary engines. The present invention relates to the use of the lubricant basestock described above in the manufacture of lubricants for turbine engines. Such engines include, for example, otto engines, diesel engines, wanckel rotary engines, and jet engines, including two-stroke engines (two-stroke engines, two-stroke engines). It can be suitably exemplified. The most preferred lubricant base stock here contains a triester of trimethylolpropane, or a tetraester of pentaerythritol and / or di-trimethylolpropane.
さらに詳しく説明しなくても、この分野の専門家であれば、上述の説明を利用して本発明を最大限に活用することができると確信する。従って、次の好ましい特定の実施形態は、例示的なものに過ぎず、いかなる場合にも開示内容の残りを限定するものではないものとして、解釈すべきである。次の例1および例2は、本発明の実施形態による(エステル油)の調合または生成(preparation)に関する。また、例3は、本発明の範囲の外にある比較用のエステルに関する。例4および例5およびテーブル1は、調合または生成されたエステル(prepared esters)の評価(evaluations)を提示する。 Without further explanation, a specialist in this field is confident that the above description can be used to make the most of the present invention. The following preferred specific embodiments are, therefore, to be construed as merely illustrative and not limiting the remainder of the disclosure in any way. The following examples 1 and 2 relate to the preparation or preparation of (ester oils) according to embodiments of the present invention. Example 3 also relates to a comparative ester that is outside the scope of the present invention. Examples 4 and 5 and Table 1 present evaluations of prepared or prepared esters.
例1
機械攪拌機、窒素パージ(nitrogen purge)、加熱機器、コンデンサ(凝縮器)およびディーンスターク装置(ウォータ・トラップ)を備えた反応槽(reaction vessel)中に、120.9gのペンタエリスリトール(pentaerythritol)、733.8gの2−プロピルヘプタン酸(2-propylheptanic acid)、触媒としての2.5gのp−トルエンスルホン酸(p-toluensulphonic)、および共沸溶媒(溶剤)(azeotropic solvent)としての43.0gのn−オクタン(n-octane)を充填した。その反応混合物を、170℃まで急速に加熱し、その後で20℃/min(分)の勾配でエステル化温度235℃に達するまで加熱を継続した。次いで、そのエステル化は、GC(ガスクロマトグラフィ)分析の結果としてその反応混合物中で1%未満のトリエステル(1つの未反応ヒドロキシル基を有するエステル)を示すまで、継続させた。次いで、15.6gの活性炭を加えて脱色を制御し、共沸溶媒および過剰なカルボン酸を蒸発させるために真空引きを適用した。3mgKOH/g未満の酸価(acid value)を有する反応生成物が得られたとき、その混合物は50℃まで冷却され、次いで、14.6gの10%(水溶液aq.)のNaOH水溶液をその反応混合物に加えた。真空引きを再び適用して、その反応混合物を100℃に再度加熱して脱水した。その結果得られた反応生成物を最後に濾過して、次の特性を有する淡黄色(pale yellow、浅黄色、黄白色)のエステル生成物が得られた。
Example 1
120.9 g pentaerythritol, 733 in a reaction vessel equipped with a mechanical stirrer, nitrogen purge, heating equipment, condenser (condenser) and Dean-Stark apparatus (water trap) 8 g 2-propylheptanic acid, 2.5 g p-toluensulphonic as catalyst, and 43.0 g as azeotropic solvent Filled with n-octane. The reaction mixture was heated rapidly to 170 ° C. and then continued to reach an esterification temperature of 235 ° C. with a gradient of 20 ° C./min (min). The esterification was then continued until GC (gas chromatography) analysis showed less than 1% triester (ester having one unreacted hydroxyl group) in the reaction mixture. 15.6 g of activated carbon was then added to control decolorization and a vacuum was applied to evaporate the azeotropic solvent and excess carboxylic acid. When a reaction product having an acid value of less than 3 mg KOH / g was obtained, the mixture was cooled to 50 ° C. and then 14.6 g of 10% (aq. Aq.) NaOH aqueous solution was added to the reaction. Added to the mixture. A vacuum was again applied and the reaction mixture was reheated to 100 ° C. and dehydrated. The resulting reaction product was finally filtered to give a pale yellow ester product having the following characteristics:
色: 144 APHA
酸価: 0.04 mg KOH/g
ヒドロキシル価: 0.23 mg KOH/g
ペンタエリスリトール テトラエステルの含有量:97重量%。
Color: 144 APHA
Acid value: 0.04 mg KOH / g
Hydroxyl number: 0.23 mg KOH / g
Content of pentaerythritol tetraester: 97% by weight.
例2
ペンタエリスリトールを同じ量のトリエチロールプロパン(trimethylolpropane)に置き換え、733.8gの代わりに561.5gの2−プロピルヘプタン酸(2-propylpeptanoic acid)を充填し、次の特性を有する淡黄色(pale yellow、浅黄色、黄白色)のエステル生成物が得られた点を相違点として、例1を繰り返した。
Example 2
Replace pentaerythritol with the same amount of trimethylolpropane, fill with 561.5 g of 2-propylpeptanoic acid instead of 733.8 g, and have the following properties: pale yellow Example 1 was repeated, with the difference that an ester product (light yellow, yellowish white) was obtained.
色: 44 APHA
酸価: 0.02 mg KOH/g
ヒドロキシル価: 0.52 mg KOH/g
トリメチロールプロパン トリエステルの含有量:97重量%。
Color: 44 APHA
Acid value: 0.02 mg KOH / g
Hydroxyl number: 0.52 mg KOH / g
Trimethylolpropane triester content: 97% by weight.
例3(比較用)
2−プロピルヘプタン酸を613.4gの2−エチルヘキサン酸(2-ethylhexanoic acid)に置き換え、次の特性を有する淡黄色(pale yellow、浅黄色、黄白色)のエステル生成物が得られた点を相違点として、例1を繰り返した。
Example 3 (for comparison)
Replacing 2-propylheptanoic acid with 613.4 g of 2-ethylhexanoic acid, a pale yellow ester product having the following characteristics was obtained: Example 1 was repeated with the difference.
色: 5 APHA
酸価: 0.03 mg KOH/g
ヒドロキシル価: 0.52 mg KOH/g
ペンタエリスリトール テトラエステルの含有量:97重量%。
Color: 5 APHA
Acid value: 0.03 mg KOH / g
Hydroxyl number: 0.52 mg KOH / g
Content of pentaerythritol tetraester: 97% by weight.
例4
例1、2および3(比較用)で得られたエステル生成物(潤滑剤ベースストック)を、潤滑剤における重要な特性に関して評価した。本発明の実施形態によるエステル生成物は実質的にまたは充分に改善された特性を示した。その結果が下記の表1に示されている。
Example 4
The ester products (lubricant basestock) obtained in Examples 1, 2 and 3 (for comparison) were evaluated for important properties in the lubricant. The ester products according to embodiments of the present invention exhibited substantially or sufficiently improved properties. The results are shown in Table 1 below.
例5
例1および例3(比較用)で得られたエステル生成物は、温度−18〜20℃で冷凍庫内に一晩(over night、夜通しで)置いた。例1の生成物は、その時間の後、透明な(clear、澄んだ)高い粘性のある(viscous、粘着性の)液体であり、例3の生成物は不透明の蝋性の固体(固形物)(opaque waxy solid)であった。
Example 5
The ester products obtained in Examples 1 and 3 (for comparison) were placed in a freezer overnight at a temperature of -18-20 ° C. The product of Example 1 is a clear, highly viscous liquid after that time, and the product of Example 3 is an opaque waxy solid (solid ) (Opaque waxy solid).
Claims (8)
前記アルキルが独立にC1−C8アルキルであり、
前記エステルが、少なくとも95重量%のトリエステルまたはテトラエステル含有量を有する、潤滑剤ベースストックの使用法。 Obtained by esterifying 2-propylheptanoic acid with at least one 2-alkyl-2-hydroxyalkyl-1,3-propanediol or at least one 2,2-dihydroxyalkyl-1,3-propanediol. A method of using a lubricant basestock comprising the use of a lubricant basestock comprising at least one ester for the manufacture of a lubricant for an internal combustion engine or turbine engine comprising:
It said alkyl is C 1 -C 8 alkyl independently,
Use of a lubricant base stock, wherein the ester has a triester or tetraester content of at least 95% by weight.
前記エステルは、少なくとも97重量%のトリエステル含有量を有するものである、請求項1乃至6のいずれかに記載の使用法。 The ester is obtained by esterifying 2-propylheptanoic acid with trimethylolpropane,
7. Use according to any one of the preceding claims, wherein the ester has a triester content of at least 97% by weight.
前記エステルは、少なくとも97重量%のテトラエステル含有量を有するものである、請求項1乃至6のいずれかに記載の使用法。 The ester is obtained by esterifying 2-propylheptanoic acid with pentaerythritol,
7. Use according to any one of the preceding claims, wherein the ester has a tetraester content of at least 97% by weight.
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SE0802280-8 | 2008-10-27 | ||
SE0802280A SE532942C2 (en) | 2008-10-27 | 2008-10-27 | Low lubricant base lubricant |
PCT/SE2009/000463 WO2010050871A1 (en) | 2008-10-27 | 2009-10-16 | Low pour point lubricant base stock |
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JP5406931B2 true JP5406931B2 (en) | 2014-02-05 |
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EP (1) | EP2342312B1 (en) |
JP (1) | JP5406931B2 (en) |
CN (1) | CN102203225B (en) |
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JP6135017B2 (en) * | 2012-02-01 | 2017-05-31 | Khネオケム株式会社 | Mixed ester |
US9523058B2 (en) | 2012-03-23 | 2016-12-20 | Kh Neochem Co., Ltd. | Mixed ester |
JPWO2015016314A1 (en) * | 2013-07-31 | 2017-03-02 | Khネオケム株式会社 | Refrigerating machine oil and working fluid composition for refrigerating machine using the same |
CN105130799A (en) * | 2015-06-30 | 2015-12-09 | 百川化工(如皋)有限公司 | Method for producing ditrimethylolpropane oleate |
CN105037146A (en) * | 2015-06-30 | 2015-11-11 | 百川化工(如皋)有限公司 | Ditrimethylolpropane laurate and preparation method thereof |
CN106329626B (en) * | 2016-08-31 | 2019-02-26 | 浙江腾腾电气有限公司 | A kind of photovoltaic charged control system of MPPT |
US11680218B2 (en) | 2018-06-04 | 2023-06-20 | Tetramer Technologies, Llc | Biodegradable lubricant with tailored hydrolytic stability and improved thermal stability through alkoxylation of glycerol |
CA3102545A1 (en) * | 2018-06-04 | 2019-12-12 | Tetramer Technologies, Llc | Lubricating base oils from esterified alkoxylated polyols using saturated long-chain fatty acids |
DE102020102162A1 (en) | 2020-01-29 | 2021-07-29 | Oq Chemicals Gmbh | TCD ester for low temperature lubricant applications |
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US3538002A (en) * | 1968-11-20 | 1970-11-03 | Monsanto Res Corp | Modified functional fluids |
IL59407A (en) * | 1979-03-06 | 1983-12-30 | Sanofi Sa | Di-n-propylacetic acid diesters of glycerol,their preparation and pharmaceutical compositions containing them |
US20030104956A1 (en) * | 1994-04-28 | 2003-06-05 | Schaefer Thomas G. | Synthetic lubricant base stock formed from high content branched chain acid mixtures |
US5744626A (en) * | 1994-10-31 | 1998-04-28 | Lambent Technologies Inc | Complex guerbet acid esters |
DE69525768T2 (en) * | 1994-12-08 | 2002-10-24 | Exxonmobil Chemical Patents Inc., Baytown | BIODEGRADABLE SYNTHETIC BRANCHED ESTERS AND LUBRICANT MADE THEREOF |
JPH09100481A (en) * | 1995-07-28 | 1997-04-15 | Chisso Corp | Lubricating oil |
SE9602465D0 (en) * | 1996-06-24 | 1996-06-24 | Perstorp Ab | A lubricant ester |
JP2000072715A (en) * | 1998-08-31 | 2000-03-07 | Idemitsu Kosan Co Ltd | Polyhydric alcohol ester compound and lubricating oil composition containing the same |
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 |
DE10305562A1 (en) * | 2003-02-10 | 2004-08-26 | Sasol Germany Gmbh | Ester mixtures based on branched alcohols and / or branched acids and their use as a polymer additive |
US20040198616A1 (en) * | 2003-03-27 | 2004-10-07 | Keiji Hirao | Lubricating base stock for internal combustion engine oil and composition containing the same |
JP2004292684A (en) * | 2003-03-27 | 2004-10-21 | Nof Corp | Lubricating oil base oil for internal combustion engine and composition containing the same |
KR101506046B1 (en) * | 2007-03-13 | 2015-03-25 | 엑손모빌 케미칼 패턴츠 인코포레이티드 | batch esterification |
JP5211752B2 (en) * | 2007-03-29 | 2013-06-12 | 日油株式会社 | Lubricating oil composition for refrigerator and working fluid composition for refrigerator using the same |
JP5406433B2 (en) * | 2007-04-27 | 2014-02-05 | 東燃ゼネラル石油株式会社 | Lubricating oil composition for internal combustion engines |
EP1990041A1 (en) * | 2007-05-07 | 2008-11-12 | Cognis IP Management GmbH | Cosmetic compositions containing esters based on 2-propylheptanoic acid |
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SE532942C2 (en) | 2010-05-18 |
US20140100149A1 (en) | 2014-04-10 |
JP2012506942A (en) | 2012-03-22 |
EP2342312A4 (en) | 2012-04-18 |
ES2659370T3 (en) | 2018-03-15 |
WO2010050871A1 (en) | 2010-05-06 |
US20110247578A1 (en) | 2011-10-13 |
EP2342312B1 (en) | 2017-11-29 |
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CN102203225A (en) | 2011-09-28 |
EP2342312A1 (en) | 2011-07-13 |
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