JPWO2016017548A1 - Lubricant composition and method for producing lubricant composition - Google Patents
Lubricant composition and method for producing lubricant composition Download PDFInfo
- Publication number
- JPWO2016017548A1 JPWO2016017548A1 JP2016538323A JP2016538323A JPWO2016017548A1 JP WO2016017548 A1 JPWO2016017548 A1 JP WO2016017548A1 JP 2016538323 A JP2016538323 A JP 2016538323A JP 2016538323 A JP2016538323 A JP 2016538323A JP WO2016017548 A1 JPWO2016017548 A1 JP WO2016017548A1
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- Prior art keywords
- lubricant composition
- oil
- carbon atoms
- ester
- mass
- Prior art date
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- Granted
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- 239000000203 mixture Substances 0.000 title claims abstract description 166
- 239000000314 lubricant Substances 0.000 title claims abstract description 137
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- 150000002148 esters Chemical class 0.000 claims abstract description 102
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 75
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 66
- 239000002131 composite material Substances 0.000 claims abstract description 65
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 32
- 239000011541 reaction mixture Substances 0.000 claims abstract description 31
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims abstract description 19
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 18
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims abstract description 18
- 229920005862 polyol Polymers 0.000 claims abstract description 17
- 150000003077 polyols Chemical class 0.000 claims abstract description 15
- 229920000728 polyester Polymers 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 239000003921 oil Substances 0.000 claims description 42
- 239000005078 molybdenum compound Substances 0.000 claims description 32
- 150000002752 molybdenum compounds Chemical class 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 26
- 229910052717 sulfur Inorganic materials 0.000 claims description 21
- 239000011593 sulfur Substances 0.000 claims description 21
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 20
- 229910052750 molybdenum Inorganic materials 0.000 claims description 16
- 239000011733 molybdenum Substances 0.000 claims description 16
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 15
- 239000004519 grease Substances 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- 229910052698 phosphorus Inorganic materials 0.000 claims description 12
- 239000011574 phosphorus Substances 0.000 claims description 12
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 11
- 239000011701 zinc Substances 0.000 claims description 11
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 10
- 239000012530 fluid Substances 0.000 claims description 10
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- 238000002485 combustion reaction Methods 0.000 claims description 9
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- 239000002480 mineral oil Substances 0.000 claims description 7
- 238000012545 processing Methods 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 238000005555 metalworking Methods 0.000 claims description 6
- 238000005520 cutting process Methods 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
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- 239000010721 machine oil Substances 0.000 claims description 3
- 239000010723 turbine oil Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
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- 230000015572 biosynthetic process Effects 0.000 description 37
- 238000003786 synthesis reaction Methods 0.000 description 37
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 26
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- 239000002609 medium Substances 0.000 description 23
- 238000000034 method Methods 0.000 description 22
- 230000000052 comparative effect Effects 0.000 description 21
- 238000005461 lubrication Methods 0.000 description 20
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- XULHFMYCBKQGEE-MRXNPFEDSA-N 2-Hexyl-1-decanol Natural products CCCCCCCC[C@H](CO)CCCCCC XULHFMYCBKQGEE-MRXNPFEDSA-N 0.000 description 14
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 14
- XULHFMYCBKQGEE-UHFFFAOYSA-N 2-hexyl-1-Decanol Chemical compound CCCCCCCCC(CO)CCCCCC XULHFMYCBKQGEE-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 238000011156 evaluation Methods 0.000 description 13
- 239000002562 thickening agent Substances 0.000 description 13
- 239000002199 base oil Substances 0.000 description 11
- 239000000344 soap Substances 0.000 description 11
- 239000000654 additive Substances 0.000 description 10
- 230000001050 lubricating effect Effects 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
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- 239000004202 carbamide Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- SMYREFDDLSTNKQ-UHFFFAOYSA-N oxocan-2-ol Chemical compound OC1CCCCCCO1 SMYREFDDLSTNKQ-UHFFFAOYSA-N 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 239000010959 steel Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 150000003673 urethanes Chemical class 0.000 description 7
- 239000001993 wax Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 6
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
- WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 235000013305 food Nutrition 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 125000005647 linker group Chemical group 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid group Chemical group C(CCCCC(=O)O)(=O)O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 239000010687 lubricating oil Substances 0.000 description 4
- 150000002751 molybdenum Chemical class 0.000 description 4
- 150000002898 organic sulfur compounds Chemical class 0.000 description 4
- 231100000241 scar Toxicity 0.000 description 4
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 3
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000005299 abrasion Methods 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 3
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 3
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- 238000005984 hydrogenation reaction Methods 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
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- 230000003647 oxidation Effects 0.000 description 3
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- XMKLTEGSALONPH-UHFFFAOYSA-N 1,2,4,5-tetrazinane-3,6-dione Chemical class O=C1NNC(=O)NN1 XMKLTEGSALONPH-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
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Abstract
本発明は、様々な温度、荷重において低摩擦化と低摩耗化を両立した潤滑剤組成物及び潤滑剤組成物の製造方法を提供することを課題とする。本発明の潤滑剤組成物は、少なくとも、3価以上のポリオールa1、炭素数36〜44の2価カルボン酸を少なくとも75質量%含有する、炭素数18〜22の不飽和脂肪酸の重合反応混合物、及び重合反応混合物を水素添加して得られた混合物、の少なくともいずれかの混合物b1、及び、下記一般式(1)で表されるモノオールc1が縮合したポリエステルを含む複合エステルAを含有する潤滑剤組成物であって、a1の水酸基mol数/b1のカルボン酸mol数/c1の水酸基mol数の仕込み比が、1/1.5〜2.0/0.7〜1.5であり、複合エステルAの含有量は、潤滑剤組成物の全質量に対して0.1〜5質量%である。一般式(1):R−OHAn object of the present invention is to provide a lubricant composition that achieves both low friction and low wear at various temperatures and loads, and a method for producing the lubricant composition. The lubricant composition of the present invention comprises a polymerization reaction mixture of unsaturated fatty acid having 18 to 22 carbon atoms, containing at least 75% by mass of trivalent or higher polyol a1 and divalent carboxylic acid having 36 to 44 carbon atoms, And a mixture obtained by hydrogenating the polymerization reaction mixture, and at least one mixture b1, and a lubricant containing a composite ester A containing a polyester condensed with a monool c1 represented by the following general formula (1) The preparation ratio of mol number of hydroxyl group of a1 / mol number of carboxylic acid of b1 / mol number of hydroxyl group of c1 is 1 / 1.5 to 2.0 / 0.7 to 1.5, Content of composite ester A is 0.1-5 mass% with respect to the total mass of a lubricant composition. General formula (1): R-OH
Description
本発明は潤滑剤組成物に関する。より詳しくは、本発明は、特定の複合エステルを含有する潤滑剤組成物であって、低摩擦性と低摩耗性を両立する潤滑剤組成物に関する。 The present invention relates to a lubricant composition. More specifically, the present invention relates to a lubricant composition containing a specific complex ester, which has both low friction and low wear properties.
近年、潤滑剤(潤滑剤組成物)においてはエネルギーロス低減の観点から低摩擦化が求められている。特に自動車においては、炭酸ガス排出低減の観点から省燃費化が強く求められており、エンジンオイルでの低摩擦化の達成が非常に重要となる。摩擦状態としては、一般的に、摩擦面間に流体オイルが存在する流体潤滑状態、摩擦面同士が接触し、摩耗しやすい境界潤滑状態、およびこれらの状態の中間である混合潤滑状態が知られている。 In recent years, lubricants (lubricant compositions) have been required to have low friction from the viewpoint of reducing energy loss. Particularly in automobiles, fuel saving is strongly demanded from the viewpoint of reducing carbon dioxide emissions, and it is very important to achieve low friction with engine oil. Generally, the friction state includes a fluid lubrication state where fluid oil exists between the friction surfaces, a boundary lubrication state where the friction surfaces are in contact with each other and easily worn, and a mixed lubrication state which is intermediate between these states. ing.
内燃機関用潤滑剤組成物を例にとると、エンジン始動時は油膜切れを起こしやすいため、境界潤滑状態になりやすい。始動から油温が上昇するまでは潤滑剤組成物の粘度が高いため、粘性抵抗が大きく、エネルギーロスとなる。また、アイドリング時には油温上昇と低速での摩擦が同時に起こるため、境界潤滑状態になりやすい。内燃機関用途以外においても潤滑剤組成物は様々な温度、荷重領域において良好な摩擦特性を発現することが求められている。 Taking a lubricant composition for an internal combustion engine as an example, the oil film is likely to be cut when the engine is started, and therefore a boundary lubrication state is likely to occur. Since the viscosity of the lubricant composition is high from the start until the oil temperature rises, the viscosity resistance is large, resulting in energy loss. In addition, during idling, oil temperature rise and friction at low speed occur at the same time, so boundary lubrication tends to occur. Even in applications other than internal combustion engines, the lubricant composition is required to exhibit good friction characteristics at various temperatures and load ranges.
潤滑剤組成物は、一般にベースオイルと種々の添加剤を含む。ベースオイルとしては、原油から得られる鉱物油、化学合成されるエステル系油、フッ素油、ポリαオレフィン系油などがある。これらの中でも、エステル系油は、低流動点、高粘度指数、高引火点、良好な潤滑特性、生分解性などから、ジェット機、自動車エンジン油、グリースなどに好適に用いられる。 The lubricant composition generally includes a base oil and various additives. Base oils include mineral oils obtained from crude oils, chemically synthesized ester oils, fluorine oils, polyalphaolefin oils, and the like. Among these, ester oils are suitably used for jet aircraft, automobile engine oils, greases and the like because of their low pour point, high viscosity index, high flash point, good lubricating properties, biodegradability, and the like.
エステル系油はベースオイルあるいは添加剤として用いることが知られている。例えば脂肪族モノカルボン酸と一価アルコールとの反応から得られるモノエステル;脂肪族二塩基酸と一価アルコールとの反応から得られるジエステル;多価アルコールと脂肪族カルボン酸との反応から得られるポリオールエステル;及びポリオール、多塩基酸、脂肪族モノカルボン酸との反応から得られる複合エステル;等、様々なエステル類が開示されている(特許文献1〜9)。 It is known that ester oils are used as base oils or additives. For example, a monoester obtained from a reaction between an aliphatic monocarboxylic acid and a monohydric alcohol; a diester obtained from a reaction between an aliphatic dibasic acid and a monohydric alcohol; obtained from a reaction between a polyhydric alcohol and an aliphatic carboxylic acid Various esters are disclosed (Patent Documents 1 to 9), such as polyol esters; and complex esters obtained by reaction with polyols, polybasic acids, and aliphatic monocarboxylic acids.
潤滑剤組成物は様々な温度、荷重領域において良好な摩擦特性を発現することが求められている。良好な摩擦特性(低摩擦化)を達成するには潤滑剤組成物の粘性抵抗低減、すなわち低粘度化により流体潤滑状態での低摩擦化が有効であるが、一方で潤滑剤組成物の低粘度化を進めていくと、境界潤滑状態における摩耗による装置の劣化が問題となる。
低摩擦化と低摩耗化を達成するために、潤滑剤組成物に様々なエステル系組成物を、所定の割合で添加することが検討されている。しかし、上述したようなエステル系組成物を用いた潤滑剤組成物においても、低摩擦化と低摩耗化の両立は十分といえず、様々な温度、荷重においてこれらを両立することは困難であった。このため、さらに良好な潤滑特性、低粘度かつ流体潤滑状態での低摩擦性、及び高温かつ高荷重のような境界潤滑状態での低摩耗性を示す潤滑剤組成物が求められている。The lubricant composition is required to exhibit good friction characteristics at various temperatures and load ranges. In order to achieve good friction properties (lower friction), it is effective to reduce the viscous resistance of the lubricant composition, that is, to lower the friction in the fluid lubrication state by lowering the viscosity, while the lower the lubricant composition. As the viscosity increases, deterioration of the apparatus due to wear in the boundary lubrication state becomes a problem.
In order to achieve low friction and low wear, it has been studied to add various ester-based compositions at a predetermined ratio to the lubricant composition. However, even in a lubricant composition using the ester-based composition as described above, it is difficult to achieve both low friction and low wear, and it is difficult to achieve both at various temperatures and loads. It was. For this reason, there is a need for a lubricant composition that exhibits even better lubricating properties, low viscosity and low friction in a fluid lubrication state, and low wear in a boundary lubrication state such as high temperature and high load.
本発明が解決しようとする課題は、様々な温度、荷重において低摩擦性と低摩耗性が両立した潤滑剤組成物を提供することである。 The problem to be solved by the present invention is to provide a lubricant composition having both low friction and low wear properties at various temperatures and loads.
本発明者は、上記の課題を解決すべく、種々検討した結果、特定の比率でアルコールとカルボン酸を仕込み縮合させたポリエステルを含む複合エステルAを特定量含有する潤滑剤組成物は、高温および/または高圧といった過酷条件においても低摩耗性及び低摩擦性を発現し得ることを見出した。
すなわち、上記課題は、以下の構成の本発明によって解決される。As a result of various studies to solve the above problems, the present inventor has found that a lubricant composition containing a specific amount of a composite ester A containing a polyester prepared by condensing an alcohol and a carboxylic acid at a specific ratio has a high temperature and It has been found that low wear and low friction can be exhibited even under severe conditions such as high pressure.
That is, the said subject is solved by this invention of the following structures.
[1]少なくとも、3価以上のポリオールa1、炭素数36〜44の2価カルボン酸を少なくとも75質量%含有する、炭素数18〜22の不飽和脂肪酸の重合反応混合物、及び重合反応混合物を水素添加して得られた混合物、の少なくともいずれかの混合物b1、及び、下記一般式(1)で表されるモノオールc1が縮合したポリエステルを含む複合エステルAを含有する潤滑剤組成物であって、a1の水酸基mol数/b1のカルボン酸mol数/c1の水酸基mol数の仕込み比が、1/1.5〜2.0/0.7〜1.5であり、複合エステルAの含有量は、潤滑剤組成物の全質量に対して0.1〜5質量%である潤滑剤組成物;
一般式(1):
R−OH
一般式(1)中、Rは炭素数8以上の直鎖アルキル基又は炭素数8以上の分岐アルキル基を表す。
[2]一般式(1)において、Rは炭素数8〜25の直鎖アルキル基又は炭素数8〜25の分岐アルキル基である[1]に記載の潤滑剤組成物。
[3]一般式(1)において、Rは炭素数16〜20の直鎖アルキル基又は炭素数16〜20の分岐アルキル基である[1]又は[2]に記載の潤滑剤組成物。
[4]一般式(1)において、Rは分岐アルキル基である[1]〜[3]のいずれかに記載の潤滑剤組成物。
[5]複合エステルAの含有量は、潤滑剤組成物の全質量に対して0.5〜2質量%である[1]〜[4]のいずれかに記載の潤滑剤組成物。
[6]a1の水酸基mol数及びc1の水酸基mol数の合計の水酸基mol数をPとし、b1のカルボン酸mol数をQとした場合、P/Qの仕込み比が、1/0.7〜0.95である[1]〜[5]のいずれかに記載の潤滑剤組成物。
[7]複合エステルAの40℃における動粘度が500〜2000mm2/sである[1]〜[6]のいずれかに記載の潤滑剤組成物。
[8]40℃における動粘度が5〜100mm2/sである[1]〜[7]のいずれかに記載の潤滑剤組成物。
[9]媒体をさらに含み、潤滑剤組成物の全質量に対し、複合エステルAを0.1〜5質量%と、媒体を70〜99.9質量%含み、潤滑剤組成物の全質量に対し、複合エステルA及び媒体以外の他の成分を0〜29.9質量%含む[1]〜[8]のいずれかに記載の潤滑剤組成物。
[10]媒体が鉱油、ポリオレフィン油、エステル油及びエーテル油から選ばれる少なくとも1種である[9]に記載の潤滑剤組成物。
[11]他の成分が亜鉛、モリブデン、硫黄及びリンのうち少なくとも1種を構成元素として有する化合物である[9]又は[10]に記載の潤滑剤組成物。
[12]他の成分が、有機モリブデン化合物及び有機亜鉛化合物の少なくとも1種である[9]〜[11]のいずれかに記載の潤滑剤組成物。
[13]グリース用潤滑油、離型剤、内燃機関用オイル、金属加工用(切削用)オイル、軸受け用オイル、燃焼機関用燃料、車両エンジン油、ギヤ油、自動車用作動油、船舶・航空機用潤滑油、マシン油,タービン油、軸受用オイル、油圧作動油、圧縮機・真空ポンプ油、冷凍機油、金属加工用潤滑油剤、磁気記録媒体用潤滑剤、マイクロマシン用潤滑剤、人工骨用潤滑剤、又は圧延油として用いられる[1]〜[12]のいずれかに記載の潤滑剤組成物。
[14]複合エステルAを得る工程と、複合エステルAの濃度が0.1〜5質量%である潤滑剤組成物を得る工程を含み、複合エステルAを得る工程は、少なくとも、3価以上のポリオールa1、炭素数36〜44の2価カルボン酸を少なくとも75質量%含有する、炭素数18〜22の不飽和脂肪酸の重合反応混合物、及び重合反応混合物を水素添加して得られた混合物、の少なくともいずれかの混合物b1、及び、下記一般式(1)で表されるモノオールc1を、a1の水酸基mol数/b1のカルボン酸mol数/c1の水酸基mol数が、1/1.5〜2.0/0.7〜1.5となるように混合し、縮合させる工程である潤滑剤組成物の製造方法;
一般式(1):
R−OH
一般式(1)中、Rは炭素数8以上の直鎖アルキル基又は炭素数8以上の分岐アルキル基を表す。[1] Polymerization reaction mixture of unsaturated fatty acid having 18 to 22 carbon atoms containing at least 75% by mass of trivalent or higher polyol a1 and divalent carboxylic acid having 36 to 44 carbon atoms, and hydrogenating the polymerization reaction mixture A lubricant composition comprising a composite ester A comprising a mixture b1 of at least one of the mixture obtained by addition and a polyester condensed with a monool c1 represented by the following general formula (1): The preparation ratio of mol number of hydroxyl groups of a1 / mol number of carboxylic acids of b1 / mol number of hydroxyl groups of c1 is 1 / 1.5 to 2.0 / 0.7 to 1.5, and the content of composite ester A Is a lubricant composition that is 0.1 to 5% by weight relative to the total weight of the lubricant composition;
General formula (1):
R-OH
In general formula (1), R represents a linear alkyl group having 8 or more carbon atoms or a branched alkyl group having 8 or more carbon atoms.
[2] The lubricant composition according to [1], wherein in general formula (1), R is a linear alkyl group having 8 to 25 carbon atoms or a branched alkyl group having 8 to 25 carbon atoms.
[3] The lubricant composition according to [1] or [2], wherein in the general formula (1), R is a linear alkyl group having 16 to 20 carbon atoms or a branched alkyl group having 16 to 20 carbon atoms.
[4] The lubricant composition according to any one of [1] to [3], wherein R in the general formula (1) is a branched alkyl group.
[5] The lubricant composition according to any one of [1] to [4], wherein the content of the composite ester A is 0.5 to 2% by mass with respect to the total mass of the lubricant composition.
[6] When the total number of moles of hydroxyl groups in a1 and the number of moles of hydroxyl groups in c1 is P and the number of moles of carboxylic acid in b1 is Q, the charging ratio of P / Q is 1 / 0.7 to The lubricant composition according to any one of [1] to [5], which is 0.95.
[7] The lubricant composition according to any one of [1] to [6], wherein the complex ester A has a kinematic viscosity at 40 ° C. of 500 to 2000 mm 2 / s.
[8] The lubricant composition according to any one of [1] to [7], wherein the kinematic viscosity at 40 ° C. is 5 to 100 mm 2 / s.
[9] The medium further includes 0.1 to 5% by mass of the composite ester A and 70 to 99.9% by mass of the medium with respect to the total mass of the lubricant composition, and the total mass of the lubricant composition On the other hand, the lubricant composition according to any one of [1] to [8], including 0 to 29.9% by mass of the component other than the composite ester A and the medium.
[10] The lubricant composition according to [9], wherein the medium is at least one selected from mineral oil, polyolefin oil, ester oil, and ether oil.
[11] The lubricant composition according to [9] or [10], wherein the other component is a compound having at least one of zinc, molybdenum, sulfur and phosphorus as a constituent element.
[12] The lubricant composition according to any one of [9] to [11], wherein the other component is at least one of an organic molybdenum compound and an organic zinc compound.
[13] Grease lubricating oil, release agent, internal combustion engine oil, metal processing (cutting) oil, bearing oil, combustion engine fuel, vehicle engine oil, gear oil, automotive hydraulic oil, ship / aircraft Lubricant, machine oil, turbine oil, bearing oil, hydraulic fluid, compressor / vacuum pump oil, refrigerator oil, metalworking lubricant, magnetic recording medium lubricant, micromachine lubricant, artificial bone lubricant The lubricant composition according to any one of [1] to [12], which is used as an agent or rolling oil.
[14] A step of obtaining a composite ester A and a step of obtaining a lubricant composition in which the concentration of the composite ester A is 0.1 to 5% by mass, and the step of obtaining the composite ester A is at least trivalent or higher. A polyol a1, a polymerization reaction mixture of unsaturated fatty acids having 18 to 22 carbon atoms, containing at least 75% by mass of a divalent carboxylic acid having 36 to 44 carbon atoms, and a mixture obtained by hydrogenating the polymerization reaction mixture. At least one of the mixture b1 and the monool c1 represented by the following general formula (1) has a mol number of hydroxyl groups of a1 / mol number of carboxylic acids of b1 / mol number of hydroxyl groups of c1 of 1 / 1.5 to A method for producing a lubricant composition, which is a step of mixing and condensing so as to be 2.0 / 0.7 to 1.5;
General formula (1):
R-OH
In general formula (1), R represents a linear alkyl group having 8 or more carbon atoms or a branched alkyl group having 8 or more carbon atoms.
本発明の潤滑剤組成物は、様々な温度、荷重において低摩擦性及び低摩耗性を発揮し得る。本発明の潤滑剤組成物は、低粘度かつ流体潤滑状態での低摩擦性に優れ、高温、高荷重のような境界潤滑状態においても低摩耗性を発揮し得る。 The lubricant composition of the present invention can exhibit low friction and low wear at various temperatures and loads. The lubricant composition of the present invention is excellent in low viscosity and low friction in a fluid lubrication state, and can exhibit low wear even in a boundary lubrication state such as high temperature and high load.
以下において、本発明について詳細に説明する。以下に記載する構成要件の説明は、代表的な実施形態や具体例に基づいてなされることがあるが、本発明はそのような実施形態に限定されるものではない。なお、本明細書において「〜」を用いて表される数値範囲は「〜」前後に記載される数値を下限値及び上限値として含む範囲を意味する。 Hereinafter, the present invention will be described in detail. The description of the constituent elements described below may be made based on representative embodiments and specific examples, but the present invention is not limited to such embodiments. In the present specification, a numerical range expressed using “to” means a range including numerical values described before and after “to” as a lower limit value and an upper limit value.
(潤滑剤組成物)
本発明の潤滑剤組成物は、少なくとも、3価以上のポリオールa1、炭素数36〜44の2価カルボン酸を少なくとも75質量%含有する、炭素数18〜22の不飽和脂肪酸の重合反応混合物、及び重合反応混合物を水素添加して得られた混合物、の少なくともいずれかの混合物b1、及び下記一般式(1)で表されるモノオールc1が縮合したポリエステルを含む複合エステルAを含有する潤滑剤組成物に関する。ここで、a1の水酸基mol数/b1のカルボン酸mol数/c1の水酸基mol数の仕込み比は、1/1.5〜2.0/0.7〜1.5であり、複合エステルAの含有量は、潤滑剤組成物の全質量に対して0.1〜5質量%である。
R−OH 一般式(1)
一般式(1)中、Rは炭素数8以上の直鎖アルキル基又は炭素数8以上の分岐アルキル基を表す。(Lubricant composition)
The lubricant composition of the present invention comprises a polymerization reaction mixture of unsaturated fatty acid having 18 to 22 carbon atoms, containing at least 75% by mass of trivalent or higher polyol a1 and divalent carboxylic acid having 36 to 44 carbon atoms, And a mixture obtained by hydrogenating the polymerization reaction mixture, and at least one mixture b1, and a lubricant containing a composite ester A containing a polyester condensed with a monool c1 represented by the following general formula (1) Relates to the composition. Here, the charging ratio of mol number of hydroxyl group of a1 / mol number of carboxylic acid of b1 / mol number of hydroxyl group of c1 is 1 / 1.5 to 2.0 / 0.7 to 1.5. Content is 0.1-5 mass% with respect to the total mass of a lubricant composition.
R-OH general formula (1)
In general formula (1), R represents a linear alkyl group having 8 or more carbon atoms or a branched alkyl group having 8 or more carbon atoms.
本発明の潤滑剤組成物に用いられる複合エステルAは、a1成分〜c1成分を、a1の水酸基mol数/b1のカルボン酸mol数/c1の水酸基mol数が、1/1.5〜2.0/0.7〜1.5、好ましくは1/1.55〜1.9/0.8〜1.4、さらに好ましくは1/1.60〜1.8/0.8〜1.3となるように仕込み、縮合反応させることにより得られる。 In the composite ester A used in the lubricant composition of the present invention, the a1 component to the c1 component have a molar number of mol of a1 / mol of carboxylic acid of b1 / mol of hydroxyl group of c1 of 1 / 1.5-2. 0 / 0.7 to 1.5, preferably 1 / 1.55 to 1.9 / 0.8 to 1.4, more preferably 1 / 1.60 to 1.8 / 0.8 to 1.3 It is obtained by charging and condensation reaction.
さらに、a1の水酸基mol数及びc1の水酸基mol数の合計の水酸基mol数をPとし、b1のカルボン酸mol数をQとした場合、P/Qの仕込み比は、1/0.7〜1.0であることが好ましく、1/0.75〜0.95であることがより好ましく、1/0.8〜0.9であることがさらに好ましい。すなわち、全水酸基mol数/全カルボン酸mol数の仕込み比が上記範囲となるように、各成分を仕込んで複合エステルAを得ることが好ましい。
このように、各成分を特定の比率で仕込み、縮合させることによって、得られる複合エステルAの架橋度、粘度、酸価、モノオール残存量などを最適な値とすることができる。このため、複合エステルAを基油等に極少量添加するだけで摩耗を抑制できるため、潤滑剤組成物は基油の粘度特性を維持したまま、耐摩耗性を発揮することができる。また、本発明では、流体潤滑状態、境界潤滑状態いずれにおいても良好な摩擦特性が得られる。Further, when the total number of moles of hydroxyl groups in a1 and the number of moles of hydroxyl groups in c1 is P and the number of moles of carboxylic acid in b1 is Q, the charging ratio of P / Q is 1 / 0.7 to 1 0.0, preferably 1 / 0.75 to 0.95, and more preferably 1 / 0.8 to 0.9. That is, it is preferable to obtain the composite ester A by charging each component so that the charging ratio of the total number of moles of hydroxyl groups / the total number of moles of carboxylic acids falls within the above range.
In this way, by charging and condensing each component at a specific ratio, the degree of cross-linking, viscosity, acid value, residual monool, etc. of the resulting composite ester A can be optimized. For this reason, since it is possible to suppress wear by adding a very small amount of the composite ester A to the base oil or the like, the lubricant composition can exhibit wear resistance while maintaining the viscosity characteristics of the base oil. Further, in the present invention, good friction characteristics can be obtained both in the fluid lubrication state and the boundary lubrication state.
複合エステルAの含有量は、潤滑剤組成物の全質量に対して0.1〜5質量%であればよく、0.3〜3質量%であることが好ましく、0.5〜2質量%であることがさらに好ましい。このように、複合エステルAは潤滑剤組成物に少量添加されるだけで良好な潤滑特性を発現する。 Content of composite ester A should just be 0.1-5 mass% with respect to the total mass of a lubricant composition, It is preferable that it is 0.3-3 mass%, 0.5-2 mass% More preferably. As described above, the composite ester A exhibits good lubricating properties only by adding a small amount to the lubricant composition.
(3価以上のポリオールa1)
3価以上のポリオールa1(a1成分あるいは単にa1と呼ぶこともある)は、アルコール性水酸基及び/又はフェノール性水酸基を分子内に3つ以上含有する化合物であり、アルコール性水酸基を3つ以上含有する化合物が好ましく、アルコール性水酸基を3〜6個有する化合物がより好ましい。
好ましい3価以上のポリオールa1は、下記一般式(a1−1)で表されるアルコールである。(Trivalent or higher polyol a1)
The trivalent or higher polyol a1 (also referred to as a1 component or simply a1) is a compound containing three or more alcoholic hydroxyl groups and / or phenolic hydroxyl groups in the molecule, and contains three or more alcoholic hydroxyl groups. And a compound having 3 to 6 alcoholic hydroxyl groups is more preferable.
Preferred trivalent or higher polyol a1 is an alcohol represented by the following general formula (a1-1).
一般式(a1−1)中、Zはm1価の連結基を表し、m1は3以上の整数を表し、3〜6が好ましく、3又は4がより好ましい。
Zは脂肪族連結基が好ましく、酸素原子で連結されていてもよいアルキレン連結基が好ましい。アルキレン連結基の炭素数は、2〜20であることが好ましく、2〜15であることがより好ましく、3〜10であることがさらに好ましく、5〜7であることが特に好ましい。また、Zは下記構造式(Z−1)で表すネオペンチル部分構造を有する連結基であることが高温での摩擦低減の観点からさらに好ましい。In General Formula (a1-1), Z represents an m1-valent linking group, m1 represents an integer of 3 or more, preferably 3 to 6, and more preferably 3 or 4.
Z is preferably an aliphatic linking group, and is preferably an alkylene linking group optionally linked by an oxygen atom. The alkylene linking group preferably has 2 to 20 carbon atoms, more preferably 2 to 15 carbon atoms, still more preferably 3 to 10 carbon atoms, and particularly preferably 5 to 7 carbon atoms. Z is more preferably a linking group having a neopentyl partial structure represented by the following structural formula (Z-1) from the viewpoint of reducing friction at high temperatures.
上記構造式(Z−1)において、*は、水酸基または他の置換基との結合部位を表す。 In the structural formula (Z-1), * represents a bonding site with a hydroxyl group or another substituent.
3価以上のポリオールa1としてはより好ましくはトリメチロールエタン、トリメチロールプロパン、グリセリンなどの3価ポリオール、ペンタエリスリトール、ジトリメチロールエタン、ジトリメチロールプロパンなどの4価ポリオール、ジペンタエリスリトールなどの5価以上のポリオールが挙げられ、トリメチロールエタン、トリメチロールプロパンが特に好ましい。 The trivalent or higher polyol a1 is more preferably a trivalent polyol such as trimethylolethane, trimethylolpropane or glycerin, a tetravalent polyol such as pentaerythritol, ditrimethylolethane or ditrimethylolpropane, or a pentavalent or higher valent such as dipentaerythritol. And trimethylolethane and trimethylolpropane are particularly preferable.
(炭素数36〜44の2価カルボン酸を少なくとも75質量%含有する、炭素数18〜22の不飽和脂肪酸の重合反応混合物、及び重合反応混合物を水素添加して得られた混合物、の少なくともいずれかの混合物b1)
炭素数36〜44の2価カルボン酸を少なくとも75質量%含有する、炭素数18〜22の不飽和脂肪酸の重合反応混合物、及び重合反応混合物を水素添加して得られた混合物、の少なくともいずれかの混合物b1(b1成分あるいは単にb1と呼ぶこともある)は、炭素数36〜44の2価カルボン酸を少なくとも75質量%含むものである。b1成分は、炭素数36〜44の2価カルボン酸を少なくとも80質量%以上含むことが好ましく、より好ましくは85質量%以上、更に好ましくは90質量%以上、特に好ましくは94質量%以上含む。すなわち、b1成分は、炭素数36〜44の2価カルボン酸を主成分とするものである。工業的に入手できる炭素数18〜22の不飽和脂肪酸の重合反応混合物には、2価カルボン酸の他にモノカルボン酸、トリカルボン酸が含まれていることがあるが、本発明で用いるb1成分は、2価カルボン酸が重合反応混合物の全質量に対して上記範囲以上含まれているものである。(At least any one of a polymerization reaction mixture of unsaturated fatty acids having 18 to 22 carbon atoms containing at least 75% by mass of a divalent carboxylic acid having 36 to 44 carbon atoms and a mixture obtained by hydrogenating the polymerization reaction mixture) Mixture b1)
A polymerization reaction mixture of an unsaturated fatty acid having 18 to 22 carbon atoms containing at least 75% by mass of a divalent carboxylic acid having 36 to 44 carbon atoms, and at least one of a mixture obtained by hydrogenating the polymerization reaction mixture The mixture b1 (also referred to as component b1 or simply b1) contains at least 75% by mass of a divalent carboxylic acid having 36 to 44 carbon atoms. The component b1 preferably contains at least 80% by mass of a divalent carboxylic acid having 36 to 44 carbon atoms, more preferably 85% by mass or more, still more preferably 90% by mass or more, and particularly preferably 94% by mass or more. That is, the b1 component is mainly composed of a divalent carboxylic acid having 36 to 44 carbon atoms. The industrially available polymerization reaction mixture of unsaturated fatty acids having 18 to 22 carbon atoms may contain monocarboxylic acid and tricarboxylic acid in addition to divalent carboxylic acid, but component b1 used in the present invention The divalent carboxylic acid is contained in the above range or more with respect to the total mass of the polymerization reaction mixture.
b1の原料となる炭素数18〜22の不飽和脂肪酸としては、ペトロセリン酸、オレイン酸、エライジン酸、バクセン酸、リノール酸、リノレン酸、α−エレオステアリン酸、β−エレオステアリン酸、プニカ酸、パリナリン酸などの炭素数18の不飽和脂肪酸(好ましくはオレイン酸、リノール酸)、カドレイン酸、アラキドン酸などの炭素数20の不飽和脂肪酸、セトレイン酸、エルカ酸などの炭素数22の不飽和脂肪酸(好ましくはエルカ酸)が挙げられる。これらの1種または2種以上を重合することにより、重合反応混合物が得られる。重合反応混合物は、蒸留などの方法により2価カルボン酸が75質量%以上となるように精製されることが好ましい。
特にb1成分は、炭素数18の不飽和脂肪酸の2量体化物、いわゆるダイマー酸、あるいは炭素数22の不飽和脂肪酸の2量体化物を75質量%以上含むことが好ましく、ダイマー酸を75質量%以上含むことが特に好ましい。
ここでダイマー酸とは、不飽和脂肪酸(通常は、炭素数18)が重合またはDiels−Alder反応等によって二量化して生じる脂肪族または脂環族ジカルボン酸をいう。ダイマー酸には多数の構造異性体が含まれている。ダイマー酸中に含まれる化合物の構造としては、例えば以下のものを例示することができる。Examples of the unsaturated fatty acid having 18 to 22 carbon atoms used as a raw material for b1 include petrothelic acid, oleic acid, elaidic acid, vaccenic acid, linoleic acid, linolenic acid, α-eleostearic acid, β-eleostearic acid, punica C18 unsaturated fatty acids such as acids and parinaric acid (preferably oleic acid and linoleic acid), C20 unsaturated fatty acids such as cadreic acid and arachidonic acid, C22 unsaturated acids such as cetreic acid and erucic acid. A saturated fatty acid (preferably erucic acid) is mentioned. A polymerization reaction mixture is obtained by polymerizing one or more of these. The polymerization reaction mixture is preferably purified by distillation or the like so that the divalent carboxylic acid is 75% by mass or more.
In particular, the component b1 preferably contains 75% by mass or more of dimerized product of unsaturated fatty acid having 18 carbon atoms, so-called dimer acid, or dimerized product of unsaturated fatty acid having 22 carbon atoms, and 75% by mass of dimer acid. % Or more is particularly preferable.
Here, the dimer acid refers to an aliphatic or alicyclic dicarboxylic acid produced by dimerization of an unsaturated fatty acid (usually having 18 carbon atoms) by polymerization or Diels-Alder reaction. Dimer acid contains a number of structural isomers. As a structure of the compound contained in dimer acid, the following can be illustrated, for example.
ダイマー酸の具体例としては、築野食品工業株式会社製 ツノダイム(登録商標)205、216、228、395が挙げられ、他にコグニス社、ユニケマ社、クローダ社製の製品を用いてもよい。 Specific examples of the dimer acid include Tsunodim (registered trademark) 205, 216, 228, and 395 manufactured by Tsukino Food Industry Co., Ltd., and products manufactured by Cognis, Unikema, and Croda may also be used.
混合物b1は、重合反応混合物を水素添加して得られた混合物を含むものであってもよい。すなわち、重合反応混合物としては、水素添加などの方法で炭素−炭素2重結合が還元されたものを用いてもよい。このような、重合反応混合物を用いることにより、得られる潤滑剤組成物の酸化耐性が向上する。水素添加されたダイマー酸としてはクローダ社製プリポール1006、1009などが挙げられる。混合物b1は、水素添加して得られた重合反応混合物であってもよく、水素添加して得られた重合反応混合物と、水素添加されていない重合反応混合物が混合されたものであってもよい。 The mixture b1 may include a mixture obtained by hydrogenating the polymerization reaction mixture. That is, as the polymerization reaction mixture, a mixture obtained by reducing the carbon-carbon double bond by a method such as hydrogenation may be used. By using such a polymerization reaction mixture, the oxidation resistance of the resulting lubricant composition is improved. Examples of the hydrogenated dimer acid include Prepol 1006 and 1009 manufactured by Croda. The mixture b1 may be a polymerization reaction mixture obtained by hydrogenation, or may be a mixture of a polymerization reaction mixture obtained by hydrogenation and a polymerization reaction mixture not hydrogenated. .
炭素数22の不飽和脂肪酸の重合反応混合物の具体例としてはエルカ酸の2量体化物が挙げられる。炭素数22の不飽和脂肪酸の2量体化物の具体例としてはクローダ社製プリポール1004が挙げられる。 Specific examples of the polymerization reaction mixture of unsaturated fatty acids having 22 carbon atoms include a dimerized product of erucic acid. As a specific example of the dimerization product of unsaturated fatty acid having 22 carbon atoms, POLIPOL 1004 manufactured by Croda Corporation is cited.
(モノオールc1)
モノオールc1(c1成分あるいは単にc1と呼ぶこともある)は、下記一般式(1)で表されるものである。
R−OH 一般式(1)
一般式(1)中、Rは炭素数8以上の直鎖アルキル基又は炭素数8以上の分岐アルキル基を表す。Rで表される直鎖アルキル基又は分岐アルキル基の炭素数は、各々、8以上であればよく、10以上が好ましく、14以上がより好ましい。また、Rで表される直鎖アルキル基又は分岐アルキル基の炭素数は、各々、8〜25であることが好ましく、14〜25であることがより好ましく、16〜20であることがさらに好ましい。なお、Rで表される直鎖アルキル基又は分岐アルキル基は、無置換の直鎖アルキル基又は無置換の分岐アルキル基であることが好ましい。(Monool c1)
The monool c1 (sometimes referred to as the c1 component or simply c1) is represented by the following general formula (1).
R-OH general formula (1)
In general formula (1), R represents a linear alkyl group having 8 or more carbon atoms or a branched alkyl group having 8 or more carbon atoms. The linear alkyl group or branched alkyl group represented by R may each have 8 or more carbon atoms, preferably 10 or more, and more preferably 14 or more. Moreover, it is preferable that carbon number of the linear alkyl group or branched alkyl group represented by R is respectively 8-25, It is more preferable that it is 14-25, It is further more preferable that it is 16-20. . In addition, it is preferable that the linear alkyl group or branched alkyl group represented by R is an unsubstituted linear alkyl group or an unsubstituted branched alkyl group.
Rで表されるアルキル基としては分岐アルキル基が好ましい。Rは、炭素数8〜25の分岐アルキル基であることがより好ましく、炭素数16〜20の分岐アルキル基であることがさらに好ましい。Rで表されるアルキル基を分岐構造とすることで、複合エステルの粘度の温度依存性を小さく抑えることができ、様々な温度領域で優れた潤滑特性を発揮することができる。 The alkyl group represented by R is preferably a branched alkyl group. R is more preferably a branched alkyl group having 8 to 25 carbon atoms, and further preferably a branched alkyl group having 16 to 20 carbon atoms. By making the alkyl group represented by R have a branched structure, the temperature dependence of the viscosity of the composite ester can be kept small, and excellent lubricating properties can be exhibited in various temperature ranges.
モノオールc1の具体例としてはオクタノール、デカノール、トリデカノール、ヘキサデカノール、オクタデカノール、2−エチルヘキサノール、2−ヘキシル−1−デカノール、炭素数14の分岐アルキルモノオール、炭素数16の分岐アルキルモノオール、炭素数18の分岐アルキルモノオール、炭素数20の分岐アルキルモノオールなどが挙げられる。より好ましい分岐アルキル基を有する具体例としては、2−エチルヘキサノール、2−ヘキシル−1−デカノール、炭素数14の分岐アルキルモノオール(例えば、日産化学社製、ファインオキソコール140N)炭素数16の分岐アルキルモノオール(例えば、日産化学社製、ファインオキソコール1600)、炭素数18の分岐アルキルモノオール(例えば、日産化学社製、ファインオキソコール180シリーズ)、炭素数20の分岐アルキルモノオール(例えば、日産化学社製、ファインオキソコール2000)が挙げられる。中でも、2−ヘキシル−1−デカノール、炭素数16の分岐アルキルモノオール(例えば、日産化学社製、ファインオキソコール1600)、炭素数18の分岐アルキルモノオール(例えば、日産化学社製、ファインオキソコール180シリーズ)、炭素数20の分岐アルキルモノオール(例えば、日産化学社製、ファインオキソコール2000)は好ましく用いられる。 Specific examples of the monool c1 include octanol, decanol, tridecanol, hexadecanol, octadecanol, 2-ethylhexanol, 2-hexyl-1-decanol, a branched alkyl monool having 14 carbon atoms, and a branched alkyl having 16 carbon atoms. Examples thereof include monools, branched alkyl monools having 18 carbon atoms, and branched alkyl monools having 20 carbon atoms. Specific examples having a more preferable branched alkyl group include 2-ethylhexanol, 2-hexyl-1-decanol, branched alkyl monool having 14 carbon atoms (for example, Fine Oxocol 140N, manufactured by Nissan Chemical Co., Ltd.) having 16 carbon atoms. Branched alkyl monools (for example, Fine Chemicals 1600 manufactured by Nissan Chemical Co., Ltd.), branched alkyl monools having 18 carbon atoms (for example, Fine Oxocol 180 series manufactured by Nissan Chemical Industries, Ltd.), branched alkyl monools having 20 carbon atoms ( For example, Nissan Chemical Co., Ltd. Fine Oxocol 2000) can be mentioned. Among them, 2-hexyl-1-decanol, branched alkyl monool having 16 carbon atoms (for example, Fine Oxocol 1600 manufactured by Nissan Chemical Co., Ltd.), branched alkyl monool having 18 carbon atoms (for example, manufactured by Nissan Chemical Industries, Fine Oxo) Cole 180 series) and branched alkyl monools having 20 carbon atoms (for example, Fine Oxocol 2000 manufactured by Nissan Chemical Co., Ltd.) are preferably used.
(その他の成分)
複合エステルAにおいては、a1〜c1以外の成分を更なる縮合原料として用いてもよい。更なる縮合原料としては、2価アルコール(好ましくは炭素数2〜40の脂肪族2価アルコール)、1価カルボン酸(好ましくは炭素数4以上の脂肪族カルボン酸、より好ましくは炭素数8以上の脂肪族カルボン酸)、b1以外の2価カルボン酸(好ましくは炭素数4〜10の脂肪族ジカルボン酸)を例示することができる。(Other ingredients)
In composite ester A, you may use components other than a1-c1 as a further condensation raw material. Further condensation materials include dihydric alcohols (preferably aliphatic dihydric alcohols having 2 to 40 carbon atoms), monovalent carboxylic acids (preferably aliphatic carboxylic acids having 4 or more carbon atoms, more preferably 8 or more carbon atoms). And aliphatic dicarboxylic acids other than b1 (preferably an aliphatic dicarboxylic acid having 4 to 10 carbon atoms).
(複合エステルA)
複合エステルAは、少なくとも、上述したような3価以上のポリオールa1と、炭素数36〜44の2価カルボン酸を少なくとも75質量%含有する、炭素数18〜22の不飽和脂肪酸の重合反応混合物、及び重合反応混合物を水素添加して得られた混合物、の少なくともいずれかの混合物b1と、R−OH(Rは炭素数8以上の直鎖アルキル基又は炭素数8以上の分岐アルキル基)で表されるモノオールc1を混合し、この混合物を縮合させることで得られる。複合エステルAは、上述したa1成分と、b1成分と、c1成分が縮合したポリエステルを少なくとも含む。(Composite ester A)
The composite ester A is a polymerization reaction mixture of at least 75% by mass of a trivalent or higher polyol a1 as described above and a divalent carboxylic acid having 36 to 44 carbon atoms, and an unsaturated fatty acid having 18 to 22 carbon atoms. And a mixture b1 obtained by hydrogenating the polymerization reaction mixture, and R-OH (wherein R is a linear alkyl group having 8 or more carbon atoms or a branched alkyl group having 8 or more carbon atoms). It is obtained by mixing the monool c1 represented and condensing this mixture. The composite ester A includes at least the polyester obtained by condensing the a1 component, the b1 component, and the c1 component.
複合エステルAは少なくともa1〜c1がランダムに縮合したポリエステルを含む混合物であり、複合エステルA中には、例えば、b1成分に由来した構造を1つのみ有する軽質分や、b1成分に由来した構造を2つ以上有するオリゴマーあるいはポリマー成分が含まれる。軽質分としては、具体的にはb1の主成分である2価カルボン酸の2つのカルボン酸のうち1つまたは2つがc1成分のモノオールと反応して得られるモノエステルまたはジエステルを挙げることができる。複合エステルAに含まれるポリエステルは、a1成分由来の構造を有しているため、架橋構造を形成でき、潤滑特性を向上させ得る。さらに、複合エステルAはa1成分に由来した構造を2つ以上有するポリエステルを含有していることが好ましい。架橋成分であるa1成分由来の構造を複数有することで、3次元架橋構造を形成することができ、潤滑特性が更に向上する。軽質分を除くオリゴマーあるいはポリマー成分の含有量はGPCの面積比で、好ましくは50%以上、より好ましくは60〜85%、更に好ましくは65〜80%である。 The composite ester A is a mixture containing a polyester in which at least a1 to c1 are randomly condensed. In the composite ester A, for example, a light component having only one structure derived from the b1 component, or a structure derived from the b1 component And an oligomer or polymer component having two or more. Specific examples of the light component include a monoester or diester obtained by reacting one or two of the two carboxylic acids of the divalent carboxylic acid that is the main component of b1 with the monool of the c1 component. it can. Since the polyester contained in the composite ester A has a structure derived from the a1 component, it can form a crosslinked structure and can improve the lubrication characteristics. Furthermore, it is preferable that the composite ester A contains a polyester having two or more structures derived from the a1 component. By having a plurality of structures derived from the a1 component, which is a crosslinking component, a three-dimensional crosslinked structure can be formed, and the lubricating properties are further improved. The content of the oligomer or polymer component excluding the light component is preferably 50% or more, more preferably 60 to 85%, still more preferably 65 to 80% in terms of the area ratio of GPC.
上述した複合エステルAの分子量はゲルパミエーションクロマトグラフィー(GPC)を用いた標準ポリスチレン換算の重量平均分子量で1000〜100000が好ましく、2000〜20000がより好ましく、3000〜10000が更に好ましい。なお、複合エステルAの分子量は、a1〜c1がランダムに縮合したポリエステルや、上述した軽質分、オリゴマーあるいはポリマー成分の各分子量の平均である。分子量を適正範囲とすることで、低粘度で良好な潤滑特性が得られる。本明細書中、ポリスチレン換算の重量平均分子量は具体的には、以下の条件で測定した値を採用する。
「HLC−8220GPC(東ソー(株)社製)装置」。カラムは「TSKgel、SuperHZM−H(東ソー(株)社製、4.6mmID×15cm)」、「TSKgel、SuperHZ4000(東ソー(株)社製、4.6mmID×15cm)」、TSKgel、SuperHZ2000(東ソー(株)社製、4.6mmID×15cm)」を3本用いた。The molecular weight of the composite ester A described above is preferably 1000 to 100,000, more preferably 2000 to 20000, and still more preferably 3000 to 10,000 in terms of weight average molecular weight in terms of standard polystyrene using gel permeation chromatography (GPC). In addition, the molecular weight of the composite ester A is an average of the molecular weights of the polyesters in which a1 to c1 are randomly condensed and the light components, oligomers, and polymer components described above. By setting the molecular weight within an appropriate range, good lubricating characteristics can be obtained with low viscosity. In the present specification, a value measured under the following conditions is specifically adopted as the weight average molecular weight in terms of polystyrene.
"HLC-8220GPC (manufactured by Tosoh Corporation)" apparatus. Columns are “TSKgel, SuperHZM-H (manufactured by Tosoh Corporation, 4.6 mm ID × 15 cm)”, “TSKgel, SuperHZ4000 (manufactured by Tosoh Corporation, 4.6 mmID × 15 cm)”, TSKgel, SuperHZ2000 (Tosoh Corporation) 3 ", 4.6 mm ID x 15 cm)" was used.
GPCの条件としては、例えば、下記の条件を採用することができる。
・溶離液 THF(テトラヒドロフラン)
・流速 0.35ml/min
・測定温度 40℃(カラム、インレット、RI)
・分析時間 20分
・試料濃度 0.1%
・サンプル注入量 10μlAs GPC conditions, for example, the following conditions can be employed.
・ Eluent THF (tetrahydrofuran)
・ Flow rate 0.35ml / min
・ Measurement temperature 40 ℃ (column, inlet, RI)
・ Analysis time 20 minutes ・ Sample concentration 0.1%
・ Sample injection volume 10μl
複合エステルA中には未反応のc1成分が含まれていてもよい。複合エステルA全量に対する未反応のc1成分の含量は10%以下が好ましく、6%以下が更に好ましく、4%以下が特に好ましい。未反応のc1成分の含有量は前述のGPC測定において、c1に該当する分子量ピークの面積比を用いて算出することができる。 The complex ester A may contain an unreacted c1 component. The content of the unreacted c1 component with respect to the total amount of the complex ester A is preferably 10% or less, more preferably 6% or less, and particularly preferably 4% or less. The content of the unreacted c1 component can be calculated using the area ratio of the molecular weight peak corresponding to c1 in the GPC measurement described above.
複合エステルAの40℃における動粘度は好ましくは400〜2000mm2/s、より好ましくは500〜2000mm2/s、さらに好ましくは500〜1500mm2/s、よりさらに好ましくは600〜1200mm2/s、特に好ましくは700〜1100mm2/sである。40℃における動粘度は具体的には、ウベローデ粘度計を用い、40.0℃の恒温水槽中で測定した値を採用する。複合エステルAの粘性を特定の領域とすることで、潤滑剤組成物の低粘度を維持したまま摩耗を抑制できる。Kinematic viscosity at 40 ° C. of complex ester A preferably 400~2000mm 2 / s, more preferably 500~2000mm 2 / s, more preferably 500~1500mm 2 / s, even more preferably 600~1200mm 2 / s, Most preferably, it is 700-1100 mm < 2 > / s. Specifically, the kinematic viscosity at 40 ° C. employs a value measured in a constant temperature water bath at 40.0 ° C. using an Ubbelohde viscometer. By setting the viscosity of the composite ester A to a specific region, wear can be suppressed while maintaining the low viscosity of the lubricant composition.
複合エステルAの酸価(サンプル1gを中和するのに要するKOHのmg数)は、0〜50mgKOH/gであることが好ましく、0〜15mgKOH/gであることがより好ましく、2〜10mgKOH/gであることがさらに好ましい。複合エステルAの酸価(サンプル1gを中和するのに要するKOHのmg数)は具体的には、JISK2501法に従い測定した値である。 The acid value of complex ester A (mg number of KOH required to neutralize 1 g of sample) is preferably 0 to 50 mgKOH / g, more preferably 0 to 15 mgKOH / g, and 2 to 10 mgKOH / g. More preferably, it is g. Specifically, the acid value of the complex ester A (the number of mg of KOH required to neutralize 1 g of the sample) is a value measured according to the JIS K2501 method.
(複合エステルAの製造方法)
複合エステルAは、a1成分〜c1成分をa1の水酸基mol数/b1のカルボン酸mol数/c1の水酸基mol数の比が、1/1.5〜2.0/0.7〜1.5、好ましくは1/1.55〜1.9/0.8〜1.4、更に好ましくは1/1.60〜1.8/0.8〜1.3となるように仕込み、縮合反応させることにより得られる。(Method for producing complex ester A)
In the composite ester A, the ratio of the a1 component to the c1 component in the ratio of mol of hydroxyl group of a1 / mol of carboxylic acid of b1 / mol of hydroxyl group of c1 is 1 / 1.5-2.0 / 0.7 to 1.5. , Preferably 1 / 1.55 to 1.9 / 0.8 to 1.4, more preferably 1 / 1.60 to 1.8 / 0.8 to 1.3, and a condensation reaction is performed. Can be obtained.
上記のようにして仕込んだ混合物を、触媒または縮合剤存在下もしくは無触媒で、縮合反応させることで、複合エステルAが得られる。
縮合の際は、加熱するか、水または低分子アルコールと共沸する溶媒を適量存在させることが望ましい。これにより複合エステルAが着色することなく、反応もスムーズに進行する。この溶媒は沸点100〜200℃の炭化水素系溶媒が好ましく、100〜170℃の炭化水素系溶媒がさらに好ましく、110〜160℃の炭化水素系溶媒が最も好ましい。これらの溶媒として、例えばトルエン、キシレン、メシチレンなどがあげられる。添加する量は、多すぎると液温がその溶媒付近となり、縮合が進行しにくくなる。一方、少なすぎると、共沸がスムーズに行かない。生産性の観点からは溶媒を用いずに縮合反応を行うことが好ましい。The composite ester A is obtained by subjecting the mixture charged as described above to a condensation reaction in the presence or absence of a catalyst or a condensing agent.
In the condensation, it is desirable to heat or to make an appropriate amount of a solvent azeotropic with water or a low molecular alcohol. As a result, the reaction proceeds smoothly without the complex ester A being colored. This solvent is preferably a hydrocarbon solvent having a boiling point of 100 to 200 ° C, more preferably a hydrocarbon solvent having a boiling point of 100 to 170 ° C, and most preferably a hydrocarbon solvent having a boiling point of 110 to 160 ° C. Examples of these solvents include toluene, xylene, mesitylene and the like. If the amount to be added is too large, the liquid temperature will be in the vicinity of the solvent and condensation will not proceed easily. On the other hand, if the amount is too small, azeotropy does not go smoothly. From the viewpoint of productivity, it is preferable to carry out the condensation reaction without using a solvent.
触媒を用いることで、反応が加速されるが、触媒除去の後処理が煩雑であり、複合エステルAの着色の原因となることから、用いないことが望ましい。しかし、用いる場合は、通常の触媒で通常の条件と操作が採用される。これに関しては、特表2001−501989号公報、特表2001−500549号公報、特表2001−507334号公報、及び特表2002−509563号公報中の参考文献を参照することができる。 Although the reaction is accelerated by using the catalyst, it is preferable not to use the catalyst because the post-treatment of removing the catalyst is complicated and the complex ester A is colored. However, when used, normal conditions and procedures are employed with normal catalysts. In this regard, reference can be made to Japanese Patent Publication Nos. 2001-501989, 2001-500499, 2001-507334, and 2002-509563.
仕込み終了後、液温120〜250℃、好ましくは130〜240℃、さらに好ましくは150〜230℃、特に好ましくは170〜230℃で反応させる。これにより水または低分子アルコールを含む溶媒が共沸され、冷却部位で冷却され、液体となることで分離される。この水は除去されればよい。低温で反応した後に更に高温で反応させてもよい。
反応時間は、仕込みのモル数より理論発生水量が計算されるので、この水量が得られる時点まで反応を行うことが好ましいが、完全に反応を完結させることは困難である。理論水発生量が60〜99%の時点で反応を終了しても、得られた複合エステルAを含有する潤滑剤組成物の潤滑特性は良好である。反応時間は1〜24時間であり、好ましくは3〜20時間、さらに好ましくは5〜18時間、最も好ましくは6〜15時間である。
より好ましい反応条件としては、無溶媒、無触媒で170〜200℃で1〜10時間(好ましくは2〜8時間)反応させた後、201℃〜240℃で更に1〜10時間(好ましくは2〜8時間)反応させることが好ましい。After completion of the preparation, the reaction is performed at a liquid temperature of 120 to 250 ° C, preferably 130 to 240 ° C, more preferably 150 to 230 ° C, and particularly preferably 170 to 230 ° C. As a result, a solvent containing water or a low molecular alcohol is azeotroped, cooled at the cooling site, and separated into a liquid. This water may be removed. After reacting at a low temperature, the reaction may be performed at a higher temperature.
As for the reaction time, since the theoretically generated water amount is calculated from the number of moles charged, it is preferable to carry out the reaction until the water amount is obtained, but it is difficult to complete the reaction completely. Even when the reaction is terminated when the theoretical water generation amount is 60 to 99%, the obtained lubricant composition containing the composite ester A has good lubricating properties. The reaction time is 1 to 24 hours, preferably 3 to 20 hours, more preferably 5 to 18 hours, and most preferably 6 to 15 hours.
More preferable reaction conditions are solvent-free and catalyst-free reaction at 170 to 200 ° C. for 1 to 10 hours (preferably 2 to 8 hours), and further 201 to 240 ° C. for 1 to 10 hours (preferably 2). (˜8 hours) It is preferable to react.
(潤滑剤組成物の複合エステルA以外の成分)
本発明は、複合エステルAを少なくとも含有する潤滑剤組成物に関するものである。例えば、潤滑剤組成物には、複合エステルAと各種添加剤及び/または媒体を添加することができる。
本発明の潤滑剤組成物は、媒体をさらに含み、潤滑剤組成物の全質量に対し、複合エステルAを0.1〜5質量%と、媒体を70〜99.9質量%含み、潤滑剤組成物の全質量に対し、複合エステルA及び媒体以外の他の成分を0〜29.9質量%含むことが好ましい。(Components other than the complex ester A of the lubricant composition)
The present invention relates to a lubricant composition containing at least composite ester A. For example, the composite ester A and various additives and / or media can be added to the lubricant composition.
The lubricant composition of the present invention further includes a medium, 0.1 to 5% by mass of the composite ester A and 70 to 99.9% by mass of the medium with respect to the total mass of the lubricant composition, It is preferable that 0-29.9 mass% of components other than composite ester A and a medium are included with respect to the total mass of a composition.
複合エステルAを添加することによる動粘度の上昇率(%)は、以下の関係式で算出することができる。以下の関係式において、NAは、複合エステルAを加えていない、媒体と他の成分のみの40℃における動粘度を表し、NBは、複合エステルAを加えた時の40℃における動粘度を表す。
動粘度上昇率(%)=[{(NB)−(NA)}/(NA)]×100
動粘度の上昇率(%)は、15%以下となることが好ましく、10%以下がより好ましく、5%以下が更に好ましく、2%以下が特に好ましく、1.5%以下が最も好ましい。動粘度上昇率が上記範囲となるように複合エステルAを添加し、本発明の潤滑剤組成物が調製されることが好ましい。The increase rate (%) of the kinematic viscosity due to the addition of the complex ester A can be calculated by the following relational expression. In the following relational expression, NA represents the kinematic viscosity at 40 ° C. of only the medium and other components without adding the complex ester A, and NB represents the kinematic viscosity at 40 ° C. when the complex ester A is added. .
Kinematic viscosity increase rate (%) = [{(NB) − (NA)} / (NA)] × 100
The rate of increase (%) in kinematic viscosity is preferably 15% or less, more preferably 10% or less, still more preferably 5% or less, particularly preferably 2% or less, and most preferably 1.5% or less. It is preferred that the lubricant composition of the present invention is prepared by adding the complex ester A so that the kinematic viscosity increase rate is in the above range.
(媒体)
媒体(基油とも呼ぶ)としては、鉱油、油脂化合物、ポリオレフィン油(例えばポリアルファオレフィン)、シリコーン油、エーテル油(例えばパーフルオロポリエーテル油、ジフェニルエーテル誘導体)、エステル油(例えば芳香族エステル油、1価脂肪酸エステル、2価脂肪酸ジエステル、ポリオールエステル潤滑油)、から選択される1種又は2種以上を挙げることができる。中でも、媒体は、鉱油、ポリオレフィン油、エステル油から選ばれる少なくとも1種であることが好ましい。(Medium)
Media (also referred to as base oil) include mineral oils, oil compounds, polyolefin oils (eg polyalphaolefins), silicone oils, ether oils (eg perfluoropolyether oils, diphenyl ether derivatives), ester oils (eg aromatic ester oils, Monovalent fatty acid ester, divalent fatty acid diester, polyol ester lubricating oil). Especially, it is preferable that a medium is at least 1 sort (s) chosen from mineral oil, polyolefin oil, and ester oil.
本発明において、「媒体」とは、一般的に「流動性液体」とよばれる媒体の全てを意味するものである。但し、室温又は使用される温度において、液状である必要はなく、液体以外にも固体及びゲル等のいずれの形態の材料も利用することができる。本発明において用いることができる媒体については特に制限はなく、用途に応じて種々の液体から選択することができる。本発明において用いることができる媒体については、特開2011−89106号公報の段落0067〜0096の記載を参照することができる。媒体の40℃における動粘度は1〜500mm2/sが好ましく、1.5〜200mm2/sがより好ましく、2〜50mm2/sがさらに好ましい。 In the present invention, the “medium” means all the media generally called “fluid liquids”. However, it is not necessary to be in a liquid state at room temperature or a temperature to be used, and any form material such as a solid and a gel can be used in addition to the liquid. There is no restriction | limiting in particular about the medium which can be used in this invention, According to a use, it can select from various liquids. Regarding the medium that can be used in the present invention, the description in paragraphs 0067 to 0096 of JP2011-89106A can be referred to. Kinematic viscosity at 40 ° C. of the medium is preferably from 1 to 500 mm 2 / s, more preferably 1.5~200mm 2 / s, more preferably 2 to 50 mm 2 / s.
媒体の粘度指数は90以上であることが好ましく、より好ましくは105以上、更に好ましくは110以上である。また媒体の粘度指数は、160以下であることが好ましい。粘度指数を上記範囲内とすることにより、粘度−温度特性および熱・酸化安定性、揮発防止性が良化し、摩耗防止性が向上する。
なお、本発明でいう粘度指数とは、JIS K 2283−1993に準拠して測定された粘度指数を意味する。The viscosity index of the medium is preferably 90 or more, more preferably 105 or more, and still more preferably 110 or more. The viscosity index of the medium is preferably 160 or less. By setting the viscosity index within the above range, the viscosity-temperature characteristics, heat / oxidation stability, and volatilization prevention properties are improved, and wear prevention properties are improved.
In addition, the viscosity index as used in the field of this invention means the viscosity index measured based on JISK2283-1993.
(複合エステルA及び媒体以外の他の成分)
複合エステルA及び媒体以外の他の成分として好ましい化合物、すなわち本発明の潤滑剤組成物への好ましい添加剤は、亜鉛、モリブデン、硫黄及びリンのうち少なくとも1種を構成元素として有する化合物である。このような化合物は、摩擦調整剤、摩耗防止剤、酸化防止剤などの機能を有する。亜鉛、モリブデン、硫黄及びリンのうち少なくとも1種を構成元素として有する化合物とは、化合物中に亜鉛、モリブデン、硫黄およびリンをいかなる状態で含んでもよい化合物を意味する。具体的には亜鉛、モリブデン、硫黄およびリンが、単体(酸化数0)、イオン、錯体などとして含まれる化合物を挙げることができる。このような化合物としては、有機モリブデン化合物、無機モリブデン化合物、有機亜鉛化合物、(亜)リン酸誘導体、有機硫黄化合物などが挙げられる。その中でも有機モリブデン化合物及び有機亜鉛化合物が好ましい。(Composite ester A and other components other than the medium)
A compound preferable as a component other than the composite ester A and the medium, that is, a preferable additive to the lubricant composition of the present invention is a compound having at least one of zinc, molybdenum, sulfur and phosphorus as a constituent element. Such compounds have functions such as friction modifiers, antiwear agents, and antioxidants. The compound having at least one of zinc, molybdenum, sulfur and phosphorus as a constituent element means a compound which may contain zinc, molybdenum, sulfur and phosphorus in any state. Specific examples include compounds containing zinc, molybdenum, sulfur, and phosphorus as simple substances (oxidation number 0), ions, complexes, and the like. Examples of such compounds include organic molybdenum compounds, inorganic molybdenum compounds, organic zinc compounds, (phosphite) phosphoric acid derivatives, organic sulfur compounds, and the like. Of these, organic molybdenum compounds and organic zinc compounds are preferred.
亜鉛、モリブデン、硫黄及びリンのうち少なくとも1種を構成元素として有する化合物は、1種のみを本発明の潤滑剤組成物に添加してもよく、2種以上を組み合わせて本発明の潤滑剤組成物に添加してもよい。亜鉛、モリブデン、硫黄およびリンのうち少なくとも1種を構成元素として有する化合物を2種以上組み合わせて本発明の潤滑剤組成物に添加する場合は、有機モリブデン化合物、無機モリブデン化合物、有機亜鉛化合物、(亜)リン酸誘導体および有機硫黄化合物のうち2種以上を組み合わせることが好ましく、有機モリブデン化合物及び有機亜鉛化合物を組み合わせることがより好ましい。 A compound having at least one of zinc, molybdenum, sulfur and phosphorus as a constituent element may be added alone to the lubricant composition of the present invention, or a combination of two or more of the lubricant composition of the present invention. It may be added to the product. When two or more compounds having at least one of zinc, molybdenum, sulfur and phosphorus as constituent elements are combined and added to the lubricant composition of the present invention, an organic molybdenum compound, an inorganic molybdenum compound, an organic zinc compound, ( Of these, it is preferable to combine two or more of phosphorous acid derivatives and organic sulfur compounds, and it is more preferable to combine organic molybdenum compounds and organic zinc compounds.
以下、有機モリブデン化合物、無機モリブデン化合物、有機亜鉛化合物、(亜)リン酸誘導体、有機硫黄化合物のそれぞれの好ましい態様について説明する。 Hereinafter, preferred embodiments of the organic molybdenum compound, the inorganic molybdenum compound, the organic zinc compound, the (phosphite) phosphoric acid derivative, and the organic sulfur compound will be described.
潤滑剤組成物に添加剤として用いられる有機モリブデン化合物としては、モリブデンジチオホスフェート(MoDTPと言われることもある)等のリンを含有する有機モリブデン化合物を挙げることができる。
別の有機モリブデン化合物としては、下式で表されるモリブデンジチオカーバメート(MoDTCと言われることもある)等の硫黄を含有する有機モリブデン化合物を挙げることができる。硫黄を含有する有機モリブデン化合物としては、例えば、硫化オキシモリブデン−N,N−ジ−オクチルジチオカルバメート(C8−Mo(DTC))、硫化オキシモリブデン−N,N−ジ−トリデシルジチオカルバメート(C16−Mo(DTC)などが好ましい。
As another organic molybdenum compound, an organic molybdenum compound containing sulfur such as molybdenum dithiocarbamate (sometimes referred to as MoDTC) represented by the following formula can be given. Examples of the organic molybdenum compound containing sulfur include sulfurized oxymolybdenum-N, N-di-octyldithiocarbamate (C 8 -Mo (DTC)), sulfurized oxymolybdenum-N, N-di-tridecyldithiocarbamate ( C 16 -Mo (DTC) and the like are preferable.
上記式中、R1〜R4は、同一であっても異なっていてもよく、それぞれ独立に炭化水素基を表す。R1〜R4は、それぞれ独立にアルキル基又はアリール基であることが好ましい。In the above formula, R 1 to R 4 may be the same or different, and each independently represents a hydrocarbon group. R 1 to R 4 are preferably each independently an alkyl group or an aryl group.
その他の硫黄を含有する有機モリブデン化合物としては、無機モリブデン化合物と硫黄含有有機化合物との錯体を挙げることができる。無機モリブデン化合物と硫黄含有有機化合物との錯体である有機モリブデン化合物に用いられる無機モリブデン化合物としては、例えば、二酸化モリブデン、三酸化モリブデン等の酸化モリブデン、オルトモリブデン酸、パラモリブデン酸、(ポリ)硫化モリブデン酸等のモリブデン酸、これらモリブデン酸の金属塩、アンモニウム塩等のモリブデン酸塩、二硫化モリブデン、三硫化モリブデン、五硫化モリブデン、ポリ硫化モリブデン等の硫化モリブデン、硫化モリブデン酸、硫化モリブデン酸の金属塩またはアミン塩、塩化モリブデン等のハロゲン化モリブデン等を挙げることができる。また、無機モリブデン化合物と硫黄含有有機化合物との錯体である有機モリブデン化合物に用いられる硫黄含有有機化合物としては、例えば、アルキル(チオ)キサンテート、チアジアゾール、メルカプトチアジアゾール、チオカーボネート、テトラハイドロカルビルチウラムジスルフィド、ビス(ジ(チオ)ハイドロカルビルジチオホスホネート)ジスルフィド、有機(ポリ)サルファイド、硫化エステル等を挙げることができる。
その他の硫黄を含有する有機モリブデン化合物としては、硫化モリブデン、硫化モリブデン酸等の硫黄含有モリブデン化合物とアルケニルコハク酸イミドとの錯体等を挙げることができる。Examples of other sulfur-containing organic molybdenum compounds include complexes of inorganic molybdenum compounds and sulfur-containing organic compounds. Examples of the inorganic molybdenum compound used in the organic molybdenum compound that is a complex of an inorganic molybdenum compound and a sulfur-containing organic compound include molybdenum oxides such as molybdenum dioxide and molybdenum trioxide, orthomolybdic acid, paramolybdic acid, and (poly) sulfurization. Molybdic acid such as molybdic acid, metal salts of these molybdic acids, molybdate such as ammonium salt, molybdenum disulfide, molybdenum trisulfide, molybdenum pentasulfide, molybdenum sulfide such as polysulfide molybdenum, molybdenum sulfide, molybdenum sulfide Examples thereof include metal salts or amine salts, and molybdenum halides such as molybdenum chloride. Examples of the sulfur-containing organic compound used in the organic molybdenum compound that is a complex of an inorganic molybdenum compound and a sulfur-containing organic compound include alkyl (thio) xanthate, thiadiazole, mercaptothiadiazole, thiocarbonate, and tetrahydrocarbyl thiuram disulfide. Bis (di (thio) hydrocarbyl dithiophosphonate) disulfide, organic (poly) sulfide, sulfurized ester and the like.
Examples of other organic molybdenum compounds containing sulfur include complexes of sulfur-containing molybdenum compounds such as molybdenum sulfide and sulfurized molybdenum acid with alkenyl succinimides.
有機モリブデン化合物としては、構成元素としてリンや硫黄を含まない有機モリブデン化合物を用いることができる。構成元素としてリンや硫黄を含まない有機モリブデン化合物としては、具体的には、モリブデン−アミン錯体、モリブデン−コハク酸イミド錯体、有機酸のモリブデン塩、アルコールのモリブデン塩などが挙げられ、中でも、モリブデン−アミン錯体、有機酸のモリブデン塩およびアルコールのモリブデン塩が好ましい。 As the organic molybdenum compound, an organic molybdenum compound that does not contain phosphorus or sulfur as a constituent element can be used. Specific examples of organic molybdenum compounds that do not contain phosphorus or sulfur as constituent elements include molybdenum-amine complexes, molybdenum-succinimide complexes, molybdenum salts of organic acids, and molybdenum salts of alcohols. Amine complexes, molybdenum salts of organic acids and molybdenum salts of alcohols are preferred.
潤滑剤組成物に添加剤として用いられる無機モリブデン化合物としては、無機モリブデン化合物と硫黄含有有機化合物との錯体である有機モリブデン化合物に用いられる無機モリブデン化合物の例として挙げたものと同様である。 The inorganic molybdenum compound used as an additive in the lubricant composition is the same as that exemplified as the inorganic molybdenum compound used for the organic molybdenum compound that is a complex of the inorganic molybdenum compound and the sulfur-containing organic compound.
潤滑剤組成物に添加剤として用いられる有機亜鉛化合物としては、下記式で表わされるジンクジチオホスフェート(ZDTP)ジンクジホスフェート(ZDP)が好ましい。 As the organic zinc compound used as an additive in the lubricant composition, zinc dithiophosphate (ZDTP) zinc diphosphate (ZDP) represented by the following formula is preferable.
上記式中、Q1、Q2、Q3、Q4は各々同じでも異なっていてもよく、それぞれ独立にイソプロピル基、ブチル基、イソブチル基、ペンチル基、イソペンチル基、ネオペンチル基、ヘキシル基、ヘプチル基、オクチル基、2−エチルヘキシル基、ノニル基、デシル基、ウンデシル基、ドデシル基、トリデシル基、イソトリデシル基、ミスチル基、パルミチル基、ステアリル基等の炭素数8〜20のアルキル基を表す。In the above formula, Q 1 , Q 2 , Q 3 and Q 4 may be the same or different, and are each independently isopropyl, butyl, isobutyl, pentyl, isopentyl, neopentyl, hexyl, heptyl Represents an alkyl group having 8 to 20 carbon atoms such as a group, an octyl group, a 2-ethylhexyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, an isotridecyl group, a misty group, a palmityl group, and a stearyl group.
上記式で表わされるジンクジチオホスフェート(ZDTP)としては、具体的にはn−ブチル−n−ペンチルジチオリン酸亜鉛(C4/C5 ZnDTP)、ジ−2−エチルヘキシルジチオリン酸亜鉛(C8 ZnDTP)又はイソプロピル−1−エチルブチルジチオリン酸亜鉛(C3/C6 ZnDTP)であることが好ましい。Specific examples of zinc dithiophosphate (ZDTP) represented by the above formula include zinc n-butyl-n-pentyldithiophosphate (C 4 / C 5 ZnDTP) and zinc di-2-ethylhexyldithiophosphate (C 8 ZnDTP). Alternatively, zinc isopropyl-1-ethylbutyldithiophosphate (C 3 / C 6 ZnDTP) is preferable.
本発明の潤滑剤組成物において、有機モリブデン化合物を用いる場合、潤滑剤組成物全質量に対して、モリブデン含量で10〜2000ppm含まれていることが好ましく、10〜1000ppm含まれていることがより好ましく、50〜800ppm含まれていることが更に好ましく、100〜600ppm含まれていることが特に好ましい。
また、有機亜鉛化合物を用いる場合、その含有量は潤滑剤組成物全質量に対して、亜鉛含量で100〜50000ppm含まれていることが好ましく、100〜30000ppm%含まれていることがより好ましく、100〜10000ppm含まれていることがさらに好ましく、200〜2000ppm含まれていることが特に好ましく、300〜1200ppm含まれていることが最も好ましい。
潤滑剤組成物中の有機モリブデン化合物や有機亜鉛化合物などの有機金属化合物の含有量を上記範囲内とすることにより、潤滑剤組成物の安定性を高めることができ、高温および/または高圧といった過酷条件での潤滑特性を改善でき、より優れた潤滑性能、摩耗抑制能を発揮することができる。In the lubricant composition of the present invention, when an organic molybdenum compound is used, the molybdenum content is preferably 10 to 2000 ppm, more preferably 10 to 1000 ppm, based on the total mass of the lubricant composition. Preferably, it is contained 50 to 800 ppm, more preferably 100 to 600 ppm.
Moreover, when using an organic zinc compound, the content thereof is preferably 100 to 50000 ppm in terms of zinc content, more preferably 100 to 30000 ppm%, based on the total mass of the lubricant composition. More preferably, it is contained in an amount of 100 to 10,000 ppm, particularly preferably 200 to 2000 ppm, and most preferably 300 to 1200 ppm.
By making the content of the organometallic compound such as the organomolybdenum compound and the organozinc compound in the lubricant composition within the above range, the stability of the lubricant composition can be improved, and severe conditions such as high temperature and / or high pressure can be achieved. The lubrication characteristics under the conditions can be improved, and more excellent lubrication performance and wear suppression ability can be exhibited.
(亜)リン酸誘導体としては、前述のジンクジチオホスフェート(ZDTP)、ジンクジホスフェート(ZDP)の他に亜リン酸エステル類、リン酸エステル類、リン酸トリクレジルなどの芳香族リン酸エステル、リン酸トリアルキルなどの脂肪族リン酸エステルを好ましい例として例示することができる。中でも、リン酸トリクレジルなどの芳香族リン酸エステル、リン酸トリアルキルなどの脂肪族リン酸エステルなどがより好ましい。 Examples of the (sub) phosphoric acid derivative include, in addition to the above-mentioned zinc dithiophosphate (ZDTP) and zinc diphosphate (ZDP), phosphites, phosphate esters, tricresyl phosphate and other aromatic phosphate esters, phosphorus Aliphatic phosphate esters such as trialkyl acids can be exemplified as preferred examples. Of these, aromatic phosphate esters such as tricresyl phosphate and aliphatic phosphate esters such as trialkyl phosphate are more preferable.
有機硫黄化合物としては、ポリスルフィド類が好ましく、ジアルキルポリスルフィドがより好ましい。 As the organic sulfur compound, polysulfides are preferable, and dialkyl polysulfide is more preferable.
複合エステルA及び媒体以外の他の成分としては、上記化合物の他に、例えば、粘度指数向上剤(好ましくはポリアルキル(メタ)アクリレート、アルキル(メタ)アクリレート−極性基を有する(メタ)アクリレート共重合体、ブタジエン、オレフィン又はアルキル化スチレンのポリマー及びコポリマー)、酸化防止剤(好ましくはヒンダードフェノール化合物、硫化アルキルフェノール化合物、芳香族アミン化合物、低硫黄過酸化物分解剤、油溶性銅化合物)、清浄剤(スルフェート、フェネート、カルボキシレート、ホスフェート及びサリシレートのアルカリ金属塩又はアルカリ土類金属塩、(ホウ酸変性)コハク酸イミド、コハク酸エステル)、分散剤(好ましくはフェネート、スルホネート、硫化フェネート、サリシレート、ナフテネート、ステアレート、カルバメート、チオカルバメート、燐誘導体、コハク酸誘導体(例えば長鎖置換アルケニルコハク酸誘導体、コハク酸イミド誘導体、ヒドロカルビル置換コハク酸化合物、コハク酸エステル、コハク酸エステルアミド)、マンニッヒ塩基)、流動点降下剤(好ましくはポリメタクリレート、ポリアクリレート、ポリアリールアミド、ハロパラフィンワックスと芳香族化合物の縮合製品、ビニルカルボキシレートポリマーならびにジアルキルフマレート、脂肪酸のビニルエステル及びアリルビニルエーテルのターポリマー)、腐食防止剤(好ましくはチアジアゾール)、シール適合剤(好ましくは有機ホスフェート、芳香族エステル、芳香族炭化水素、エステル(例えば、ブチルベンジルフタレート)及びポリブテニル無水コハク酸)、消泡剤(好ましくはポリジメチルシリコーン)、錆防止剤、摩擦調整剤、摩耗防止剤、及び増ちょう剤から選択される1種又は2種以上を挙げることができる。
このような添加剤を添加することにより、摩耗抑制等の潤滑剤組成物としての好ましい機能を付与することができる。本発明において用いることができる添加剤については、特開2011−89106号公報の段落0098〜0165の記載を参照することができる。In addition to the compound E and other components than the compound A, for example, a viscosity index improver (preferably polyalkyl (meth) acrylate, alkyl (meth) acrylate- (meth) acrylate having a polar group) Polymers, copolymers of butadiene, olefins or alkylated styrenes), antioxidants (preferably hindered phenol compounds, sulfurized alkylphenol compounds, aromatic amine compounds, low sulfur peroxide decomposers, oil-soluble copper compounds), Detergents (sulfate, phenate, carboxylate, phosphate and salicylate alkali metal salts or alkaline earth metal salts, (boric acid modified) succinimides, succinates), dispersants (preferably phenates, sulfonates, sulfurized phenates, Salicylate, naphth Nates, stearates, carbamates, thiocarbamates, phosphorus derivatives, succinic acid derivatives (eg long chain substituted alkenyl succinic acid derivatives, succinimide derivatives, hydrocarbyl substituted succinic acid compounds, succinic acid esters, succinic acid ester amides), Mannich bases) Pour point depressants (preferably polymethacrylates, polyacrylates, polyarylamides, condensation products of haloparaffin waxes and aromatic compounds, vinyl carboxylate polymers and dialkyl fumarate, terpolymers of fatty acid vinyl esters and allyl vinyl ethers), Corrosion inhibitors (preferably thiadiazole), seal compatibilizers (preferably organic phosphates, aromatic esters, aromatic hydrocarbons, esters (eg butyl benzyl phthalate) and polybutenis Succinic anhydride), defoamers (preferably polydimethyl silicones), rust inhibitors, friction modifiers, mention may be made of anti-wear agents, and one or more selected from thickener.
By adding such an additive, a preferable function as a lubricant composition such as wear suppression can be imparted. For the additives that can be used in the present invention, the description in paragraphs 0098 to 0165 of JP2011-89106A can be referred to.
(潤滑剤組成物の性質)
本発明の潤滑剤組成物は、40℃での動粘度が500mm2/s以下であることが好ましく、200mm2/s以下であることがより好ましく、100mm2/s以下であることがさらに好ましく、50mm2/s以下であることが特に好ましく、5〜50mm2/sであることが最も好ましい。粘性は、使用環境により適正な粘性が求められるため、それに合わせることが必要である。本明細書中、潤滑剤組成物の40℃での動粘度は具体的には、ウベローデ粘度計を用い、40.0℃の恒温水槽中で測定した値を採用する。(Properties of lubricant composition)
The lubricant composition of the present invention preferably has a kinematic viscosity at 40 ° C. of 500 mm 2 / s or less, more preferably 200 mm 2 / s or less, and even more preferably 100 mm 2 / s or less. , particularly preferably not more than 50 mm 2 / s, and most preferably from 5 to 50 mm 2 / s. Viscosity needs to be adjusted to an appropriate viscosity depending on the usage environment. In this specification, the kinematic viscosity at 40 ° C. of the lubricant composition is specifically a value measured in a constant temperature water bath at 40.0 ° C. using an Ubbelohde viscometer.
(潤滑剤組成物の製造方法)
本発明は、複合エステルAを得る工程と、複合エステルAの濃度が0.1〜5質量%である潤滑剤組成物の製造方法に関するものであり、このような製造方法によって製造された潤滑剤組成物に関するものでもある。複合エステルAを得る工程は、少なくとも、3価以上のポリオールa1、炭素数36〜44の2価カルボン酸を少なくとも75質量%含有する、炭素数18〜22の不飽和脂肪酸の重合反応混合物、及び重合反応混合物を水素添加して得られた混合物、の少なくともいずれかの混合物b1、及び、下記一般式(1)で表されるモノオールc1を、a1の水酸基mol数/b1のカルボン酸mol数/c1の水酸基mol数が、1/1.5〜2.0/0.7〜1.5となるように混合し、縮合させる工程である。
一般式(1):
R−OH
一般式(1)中、Rは炭素数8以上の直鎖アルキル基又は炭素数8以上の分岐アルキル基を表す。
a1成分〜c1成分の混合比率は、a1の水酸基mol数/b1のカルボン酸mol数/c1の水酸基mol数が、1/1.5〜2.0/0.7〜1.5であればよく、好ましくは1/1.55〜1.9/0.8〜1.4、更に好ましくは1/1.60〜1.8/0.8〜1.3である。(Method for producing lubricant composition)
The present invention relates to a step of obtaining a composite ester A and a method for producing a lubricant composition having a concentration of the composite ester A of 0.1 to 5% by mass, and the lubricant produced by such a production method. It also relates to the composition. The step of obtaining the complex ester A includes at least 75% by mass of a trivalent or higher polyol a1, a divalent carboxylic acid having 36 to 44 carbon atoms, and a polymerization reaction mixture of unsaturated fatty acids having 18 to 22 carbon atoms, and The mixture b1 obtained by hydrogenating the polymerization reaction mixture, and the monool c1 represented by the following general formula (1) are converted into the number of mols of hydroxyl groups of a1 / the number of mols of carboxylic acids of b1. This is a step of mixing and condensing so that the mol number of hydroxyl groups of / c1 is 1 / 1.5 to 2.0 / 0.7 to 1.5.
General formula (1):
R-OH
In general formula (1), R represents a linear alkyl group having 8 or more carbon atoms or a branched alkyl group having 8 or more carbon atoms.
The mixing ratio of the a1 component to the c1 component is such that the mol number of hydroxyl groups of a1 / mol number of carboxylic acids of b1 / mol number of hydroxyl groups of c1 is 1 / 1.5 to 2.0 / 0.7 to 1.5. It is preferably 1 / 1.55 to 1.9 / 0.8 to 1.4, more preferably 1 / 1.60 to 1.8 / 0.8 to 1.3.
本発明の潤滑剤組成物は、複合エステルAを、濃度が0.1〜5質量%となるように油性媒体中もしくは水性媒体中に添加し、溶解及び/又は分散させることで調製することができる。溶解及び/又は分散は、加温下で行ってもよい。 The lubricant composition of the present invention can be prepared by adding the complex ester A in an oily medium or an aqueous medium so as to have a concentration of 0.1 to 5% by mass, and dissolving and / or dispersing it. it can. Dissolution and / or dispersion may be performed under heating.
本発明の潤滑剤組成物は、グリース組成物として調製してもよい。当該態様では、グリースの用途に適応した場合の実用性能を確保するため、さらに必要に応じて、増ちょう剤等を本発明の目的を損なわない範囲で適宜添加することができる。グリース組成物の一態様は、更に増ちょう剤を10〜50質量%含有する組成物である。以下、グリース組成物として調製する際に添加可能な添加剤について説明する。 The lubricant composition of the present invention may be prepared as a grease composition. In this aspect, in order to ensure practical performance when adapted to the application of grease, a thickener or the like can be added as necessary within a range that does not impair the object of the present invention. One embodiment of the grease composition is a composition further containing 10 to 50% by mass of a thickener. Hereinafter, additives that can be added when preparing the grease composition will be described.
添加可能な増ちょう剤の例には、金属石けん、複合金属石けん等の石けん系増ちょう剤、ベントン、シリカゲル、ウレア系増ちょう剤(ウレア化合物、ウレア・ウレタン化合物、ウレタン化合物等)の非石けん系増ちょう剤などのあらゆる増ちょう剤が使用可能である。これらの中でも、樹脂製部材を損傷させるおそれが小さいことから、石けん系増ちょう剤、ウレア系増ちょう剤が好ましく用いられる。 Examples of thickeners that can be added include soaps such as metal soaps and composite metal soaps, benton, silica gel, urea thickeners (urea compounds, urea / urethane compounds, urethane compounds, etc.) Any thickener such as a series thickener can be used. Among these, a soap-based thickener and a urea-based thickener are preferably used because they are less likely to damage the resin member.
石けん系増ちょう剤としては、例えば、ナトリウム石けん、カルシウム石けん、アルミニウム石けん、リチウム石けん等が挙げられるが、これらの中でも、耐水性や熱安定性の点から、リチウム石けんが好ましい。リチウム石けんとしては、例えば、リチウムステアレートやリチウム−12−ヒドロキシステアレート等が挙げられる。 Examples of the soap-based thickener include sodium soap, calcium soap, aluminum soap, and lithium soap. Among these, lithium soap is preferable from the viewpoint of water resistance and thermal stability. Examples of lithium soap include lithium stearate and lithium-12-hydroxystearate.
また、ウレア系増ちょう剤としては、例えば、ウレア化合物、ウレア・ウレタン化合物、ウレタン化合物又はこれらの混合物等が挙げられる。 Examples of urea thickeners include urea compounds, urea / urethane compounds, urethane compounds, and mixtures thereof.
ウレア化合物、ウレア・ウレタン化合物及びウレタン化合物としては、例えば、ジウレア化合物、トリウレア化合物、テトラウレア化合物、ポリウレア化合物(ジウレア化合物、トリウレア化合物及びテトラウレア化合物は除く)、ウレア・ウレタン化合物、ジウレタン化合物又はこれらの混合物等が挙げられる。好ましくはジウレア化合物、ウレア・ウレタン化合物、ジウレタン化合物又はこれらの混合物が挙げられる。 Examples of urea compounds, urea / urethane compounds and urethane compounds include diurea compounds, triurea compounds, tetraurea compounds, polyurea compounds (excluding diurea compounds, triurea compounds and tetraurea compounds), urea / urethane compounds, diurethane compounds or mixtures thereof. Etc. Preferably, a diurea compound, a urea / urethane compound, a diurethane compound or a mixture thereof is used.
固体潤滑剤としては、例えば、ポリテトラフルオロエチレン、窒化ホウ素、フラーレン、黒鉛、フッ化黒鉛、メラミンシアヌレート、二硫化モリブデン、Mo−ジチオカーバメート、硫化アンチモン、アルカリ(土類)金属ほう酸塩等が挙げられる。 Examples of solid lubricants include polytetrafluoroethylene, boron nitride, fullerene, graphite, fluorinated graphite, melamine cyanurate, molybdenum disulfide, Mo-dithiocarbamate, antimony sulfide, and alkali (earth) metal borates. Can be mentioned.
ワックスとしては、例えば、天然ワックス、鉱油系ないしは合成系の各種ワックスが例示でき、具体的にはモンタンワックス、カルナウバワックス、高級脂肪酸のアミド化合物、パラフィンワックス、マイクロクリスタリンワックス、ポリエチレンワックス、ポリオレフィンワックス、エステルワックス等が挙げられる。 Examples of the wax include natural waxes, mineral oils and various synthetic waxes, and specifically include montan wax, carnauba wax, amide compounds of higher fatty acids, paraffin wax, microcrystalline wax, polyethylene wax, polyolefin wax. And ester wax.
その他、金属不活性化剤としてベンゾトリアゾール、ベンズイミダゾール、チアジアゾールなどが知られていて、これらを添加することができる。 In addition, benzotriazole, benzimidazole, thiadiazole and the like are known as metal deactivators, and these can be added.
グリース組成物には、増粘剤を添加することができる。増粘剤としては、例えば、ポリメタクリレート、ポリイソブチレン、ポリスチレン等が挙げられる。ポリ(メタ)アクリレートは、寒冷地での冷時異音防止の効果も知られている。 A thickener can be added to the grease composition. Examples of the thickener include polymethacrylate, polyisobutylene, polystyrene and the like. Poly (meth) acrylate is also known to prevent cold abnormal noise in cold regions.
(潤滑剤組成物の用途)
本発明の潤滑剤組成物は、例えば、2つの摺動面間に供給され、摩擦を低減するために用いることができる。本発明の潤滑剤組成物は、摺動面に皮膜を形成し得る。摺動面の材質としては、鋼鉄では、具体的には、機械構造用炭素鋼、ニッケルクロム鋼材・ニッケルクロムモリブデン鋼材・クロム鋼材・クロムモリブデン鋼材・アルミニウムクロムモリブデン鋼材などの構造機械用合金鋼、ステンレス鋼、マルチエージング鋼などが挙げられる。(Use of lubricant composition)
The lubricant composition of the present invention can be supplied, for example, between two sliding surfaces and used to reduce friction. The lubricant composition of the present invention can form a film on the sliding surface. As for the material of the sliding surface, in steel, specifically, carbon steel for machine structure, alloy steel for structural machinery such as nickel chrome steel, nickel chrome molybdenum steel, chrome steel, chrome molybdenum steel, aluminum chrome molybdenum steel, Examples include stainless steel and multi-aged steel.
摺動面の材質としては、鋼鉄以外の各種金属、又は金属以外の無機もしくは有機材料も広く用いられる。金属以外の無機もしくは有機材料としては、各種プラスチック、セラミック、カーボン等、及びその混合体などが挙げられる。より具体的には、鋼鉄以外の金属材料としては、鋳鉄、銅・銅−鉛・アルミニウム合金、その鋳物及びホワイトメタルが挙げられる。
なお、摺動面の材質については、特開2011−89106号公報の段落0168〜0175の記載を参照することができる。As the material of the sliding surface, various metals other than steel, or inorganic or organic materials other than metals are widely used. Examples of inorganic or organic materials other than metals include various plastics, ceramics, carbon, etc., and mixtures thereof. More specifically, examples of the metal material other than steel include cast iron, copper / copper-lead / aluminum alloy, castings thereof, and white metal.
In addition, about the material of a sliding surface, description of Paragraphs 0168-0175 of Unexamined-Japanese-Patent No. 2011-89106 can be referred.
本発明の潤滑剤組成物は、種々の用途に利用できる。例えば、グリース用潤滑油、離型剤、内燃機関用オイル、内燃機関用エンジンオイル、金属加工用(切削用)オイル、軸受け用オイル、燃焼機関用燃料、車両エンジン油、ギヤ油、自動車用作動油、船舶・航空機用潤滑油、マシン油,タービン油、軸受用オイル、油圧作動油、圧縮機・真空ポンプ油、冷凍機油、金属加工用潤滑油剤、磁気記録媒体用潤滑剤、マイクロマシン用潤滑剤、人工骨用潤滑剤、ショックアブソーバ油又は圧延油として用いることができる。さらに、往復動式や回転式の密閉型圧縮機を有するエアコンや冷蔵庫、自動車用エアコンや除湿機、冷凍庫、冷凍冷蔵倉庫、自動販売機、ショーケース、化学プラント等の冷却装置などにも用いられる。 The lubricant composition of the present invention can be used for various applications. For example, grease lubricant, mold release agent, internal combustion engine oil, internal combustion engine oil, metal working (cutting) oil, bearing oil, combustion engine fuel, vehicle engine oil, gear oil, automotive operation Oil, Marine / Aircraft Lubricant, Machine Oil, Turbine Oil, Bearing Oil, Hydraulic Oil, Compressor / Vacuum Pump Oil, Refrigerator Oil, Metalworking Lubricant, Magnetic Recording Medium Lubricant, Micromachine Lubricant It can be used as a lubricant for artificial bone, shock absorber oil or rolling oil. It is also used for air conditioners and refrigerators with reciprocating and rotary hermetic compressors, automotive air conditioners and dehumidifiers, freezers, refrigerated warehouses, vending machines, showcases, chemical plant and other cooling devices. .
塩素系化合物を含まない金属加工用潤滑油剤として、例えば鉄鋼材料やAl合金などの金属材料を熱間圧延したり、切削等の加工を行ったりする際に、またアルミニウムの冷間圧延油、切削油、研削油、引き抜き加工油、プレス加工油等の金属加工油や金属の塑性加工油として、特に高速、高負荷加工時の摩耗、破損、表面あれの抑止剤として、またブローチ加工,ガンドリル加工のような低速・重切削に適用可能な金属加工油組成物としても有用である。
また各種グリース用潤滑油、磁気記録媒体用潤滑剤、マイクロマシン用潤滑剤や人工骨用潤滑剤等に利用することができる。また、組成物の元素組成を炭水化物とすることができるため、例えば、乳化、分散化、可溶化剤としてケーキミックス、サラダドレッシング、ショートニングオイル、チョコレート等に広く利用されている、ポリオキシエチレンエーテルを含むソルビタン脂肪酸エステルを食用油を基油とした組成物を潤滑油とすることで、全く人体に無害の高性能潤滑油を食品製造ラインの製造機器や医療機器部材の潤滑に用いることができる。
さらに、本発明の潤滑剤組成物を水系に乳化して分散したり、極性溶媒中や樹脂媒体中に分散したりすることで、切削油や圧延油として用いることができる。As a lubricant for metal processing that does not contain chlorine-based compounds, for example, when hot-rolling metal materials such as steel materials and Al alloys, or when performing processing such as cutting, cold rolling oil of aluminum, cutting Oil, grinding oil, drawing oil, metal working oil such as press working oil and metal plastic working oil, especially as a deterrent to wear, breakage and surface roughness during high speed and high load processing, broaching, gun drilling It is also useful as a metalworking oil composition that can be applied to low speed and heavy cutting.
Further, it can be used for various grease lubricants, magnetic recording medium lubricants, micromachine lubricants, artificial bone lubricants, and the like. In addition, since the elemental composition of the composition can be a carbohydrate, for example, polyoxyethylene ether widely used in cake mix, salad dressing, shortening oil, chocolate, etc. as an emulsifying, dispersing or solubilizing agent is used. By using the composition of the sorbitan fatty acid ester containing edible oil as the base oil as the lubricating oil, a high-performance lubricating oil that is completely harmless to the human body can be used for lubrication of food production line manufacturing equipment and medical equipment members.
Furthermore, the lubricant composition of the present invention can be used as cutting oil or rolling oil by emulsifying and dispersing it in an aqueous system or by dispersing it in a polar solvent or a resin medium.
また、本発明の潤滑剤組成物は離型剤としても、種々の用途に利用できる。例えば、ポリカーボネート樹脂、難燃性ポリカーボネート樹脂、電子写真装置や静電記録装置などで使用される画像形成用トナーの主成分である結晶性ポリエステル樹脂、各種成形用熱可塑性樹脂組成物及び半導体封し用エポキシ樹脂組成物などの離型剤として用いられる。
また、衣料などの繊維製品に予め練り込んだり、塗布したりすることにより、繊維製品に付着した汚れの離脱を促進して繊維製品の汚れを防止する防汚剤としても用いることができる。Moreover, the lubricant composition of the present invention can be used for various applications as a release agent. For example, polycarbonate resin, flame retardant polycarbonate resin, crystalline polyester resin which is the main component of image forming toner used in electrophotographic apparatus and electrostatic recording apparatus, various molding thermoplastic resin compositions and semiconductor encapsulating Used as a mold release agent for epoxy resin compositions.
Moreover, it can also be used as an antifouling agent that promotes the detachment of dirt adhering to the fiber product and prevents the fiber product from being soiled by being kneaded or applied in advance to a textile product such as clothing.
以下に実施例と比較例を挙げて本発明の特徴をさらに具体的に説明する。以下の実施例に示す材料、使用量、割合、処理内容、処理手順等は、本発明の趣旨を逸脱しない限り適宜変更することができる。したがって、本発明の範囲は以下に示す具体例により限定的に解釈されるべきものではない。 The features of the present invention will be described more specifically with reference to examples and comparative examples. The materials, amounts used, ratios, processing details, processing procedures, and the like shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the specific examples shown below.
<複合エステルA−1の合成>
a1成分としてトリメチロールプロパン9.38g、b1成分としてダイマー酸(築野食品社製ツノダイム395、C36ジカルボン酸含率95%)100.0g、c1成分として2−ヘキシル−1−デカノール(日産化学社製ファインオキソコール1600)50.6g(a1の水酸基mol数/b1のカルボン酸mol数/モノオールの水酸基mol数の比=1/1.7/1)をディーンスターク脱水装置がついた反応容器に仕込んだ。a1〜c1成分の混合物を0.3L/minの窒素気流下190℃で5時間、更に220℃で4時間反応させた。反応中に発生した水は除去した。反応物を室温まで放冷し、黄色透明の液状物として複合エステルA−1を得た。<Synthesis of Complex Ester A-1>
9.38 g of trimethylolpropane as a1 component, 100.0 g of dimer acid (Tsunodaim 395 manufactured by Tsuno Foods Co., Ltd., 95% C36 dicarboxylic acid content) as b1 component, 2-hexyl-1-decanol (Nissan Chemical Co., Ltd.) as c1 component Fine Oxocol 1600) 50.6 g (ratio of mol of hydroxyl group of a1 / mol of carboxylic acid of b1 / mol of hydroxyl group of monool = 1 / 1.7 / 1) equipped with a Dean-Stark dehydrator Was charged. The mixture of components a1 to c1 was reacted at 190 ° C. for 5 hours and further at 220 ° C. for 4 hours under a nitrogen stream of 0.3 L / min. Water generated during the reaction was removed. The reaction product was allowed to cool to room temperature to obtain composite ester A-1 as a yellow transparent liquid.
<複合エステルA−2の合成>
a1成分としてトリメチロールプロパン、b1成分としてダイマー酸(築野食品社製ツノダイム228、C36ジカルボン酸含率81%)、c1成分として2−ヘキシル−1−デカノール(日産化学社製ファインオキソコール1600)を用い、a1の水酸基mol数/b1のカルボン酸mol数/モノオールの水酸基mol数の比が1/1.7/1となるように仕込んだ。これをA−1の合成と同じ手法を用いて縮合し複合エステルA−2を得た。<Synthesis of Complex Ester A-2>
Trimethylolpropane as the a1 component, dimer acid as the b1 component (Tsunodaim 228 manufactured by Tsuno Foods Co., Ltd., C36 dicarboxylic acid content 81%), 2-hexyl-1-decanol as the c1 component (Fineoxocol 1600 manufactured by Nissan Chemical Co., Ltd.) Was used so that the ratio of mol number of hydroxyl group of a1 / mol number of carboxylic acid of b1 / mol number of hydroxyl group of monool was 1 / 1.7 / 1. This was condensed using the same method as the synthesis of A-1 to obtain a complex ester A-2.
<複合エステルA−3の合成>
a1成分としてトリメチロールプロパン、b1成分としてダイマー酸(築野食品社製ツノダイム216、C36ジカルボン酸含率79%)、c1成分として2−ヘキシル−1−デカノール(日産化学社製ファインオキソコール1600)を用い、a1の水酸基mol数/b1のカルボン酸mol数/モノオールの水酸基mol数の比が1/1.7/1となるように仕込んだ。これをA−1の合成と同じ手法を用いて縮合し複合エステルA−3を得た。<Synthesis of Complex Ester A-3>
Trimethylolpropane as the a1 component, dimer acid as the b1 component (Tsunodaim 216 manufactured by Tsukuno Foods Co., Ltd., C36 dicarboxylic acid content 79%), 2-hexyl-1-decanol as the c1 component (Fineoxocol 1600 manufactured by Nissan Chemical Co., Ltd.) Was used so that the ratio of mol number of hydroxyl group of a1 / mol number of carboxylic acid of b1 / mol number of hydroxyl group of monool was 1 / 1.7 / 1. This was condensed using the same method as the synthesis of A-1 to obtain a composite ester A-3.
<複合エステルA−4の合成>
a1成分としてトリメチロールプロパン、b1成分として水素添加されたダイマー酸(クローダ社製プリポール1009、C36ジカルボン酸含率98%)、c1成分として2−ヘキシル−1−デカノール(日産化学社製ファインオキソコール1600)を用い、a1の水酸基mol数/b1のカルボン酸mol数/モノオールの水酸基mol数の比が1/1.7/1となるように仕込んだ。これをA−1の合成と同じ手法を用いて縮合し複合エステルA−4を得た。<Synthesis of Complex Ester A-4>
Trimethylolpropane as the a1 component, dimer acid hydrogenated as the b1 component (Prepol 1009 manufactured by Croda, 98% C36 dicarboxylic acid content), 2-hexyl-1-decanol (fine oxocol manufactured by Nissan Chemical Co., Ltd.) as the c1 component 1600), and charged so that the ratio of mol number of hydroxyl group of a1 / mol number of carboxylic acid of b1 / mol number of hydroxyl group of monool was 1 / 1.7 / 1. This was condensed using the same method as the synthesis of A-1 to obtain a composite ester A-4.
<複合エステルA−5の合成>
a1成分としてトリメチロールプロパン、b1成分としてC44のジカルボン酸を主成分とする重合物(クローダ社製プリポール1004、C44ジカルボン酸含率95%)、c1成分として2−ヘキシル−1−デカノール(日産化学社製ファインオキソコール1600)を用い、a1の水酸基mol数/b1のカルボン酸mol数/モノオールの水酸基mol数の比が1/1.7/1となるように仕込んだ。これをA−1の合成と同じ手法を用いて縮合し複合エステルA−5を得た。<Synthesis of Complex Ester A-5>
A polymer mainly composed of trimethylolpropane as a1 component, C44 dicarboxylic acid as b1 component (Cropa prepor 1004, C44 dicarboxylic acid content 95%), and 2-hexyl-1-decanol (Nissan Chemical) as c1 component Fine oxocol 1600) was used, and charged so that the ratio of mol of a1 hydroxyl group / mol of carboxylic acid of b1 / mol of hydroxyl group of monool was 1 / 1.7 / 1. This was condensed using the same method as the synthesis of A-1 to obtain a complex ester A-5.
<複合エステルA−6の合成>
a1成分としてトリメチロールプロパン、b1成分としてダイマー酸(築野食品社製ツノダイム395、C36ジカルボン酸含率95%)、c1成分として2−エチルヘキサノールを用い、a1の水酸基mol数/b1のカルボン酸mol数/モノオールの水酸基mol数の比が1/1.7/1となるように仕込んだ。これをA−1の合成と同じ手法を用いて縮合し複合エステルA−6を得た。<Synthesis of Complex Ester A-6>
Trimethylolpropane is used as the a1 component, dimer acid is used as the b1 component (Tsunodaim 395 manufactured by Tsuno Foods Co., Ltd., C36 dicarboxylic acid content: 95%), 2-ethylhexanol is used as the c1 component, and the number of moles of hydroxyl group of a1 / carboxylic acid of b1 The mixture was prepared so that the ratio of mol number / mol number of monool hydroxyl group was 1 / 1.7 / 1. This was condensed using the same method as the synthesis of A-1 to obtain a complex ester A-6.
<複合エステルA−7の合成>
a1成分としてトリメチロールプロパン、b1成分としてC44のジカルボン酸を主成分とする重合物(クローダ社製プリポール1004、C44ジカルボン酸含率95%)、c1成分として2−エチルヘキサノールを用い、a1の水酸基mol数/b1のカルボン酸mol数/モノオールの水酸基mol数の比が1/1.7/1となるように仕込んだ。これをA−1の合成と同じ手法を用いて縮合し複合エステルA−7を得た。<Synthesis of Complex Ester A-7>
Polymer having a main component of C44 dicarboxylic acid as a1 component (a polpol 1004, C44 dicarboxylic acid content of 95%) as b1 component, 2-ethylhexanol as c1 component, hydroxyl group of a1 The mixture was charged so that the ratio of mol number / b1 carboxylic acid mol number / monool hydroxyl group mol number was 1 / 1.7 / 1. This was condensed using the same method as the synthesis of A-1 to obtain a complex ester A-7.
<複合エステルA−8の合成>
a1成分としてトリメチロールプロパン、b1成分としてダイマー酸(築野食品社製ツノダイム395、C36ジカルボン酸含率95%)、c1成分として2−エチルヘキサノールを用い、a1の水酸基mol数/b1のカルボン酸mol数/モノオールの水酸基mol数の比が1/1.5/0.75となるように仕込んだ。これをA−1の合成と同じ手法を用いて縮合し複合エステルA−8を得た。<Synthesis of Complex Ester A-8>
Trimethylolpropane is used as the a1 component, dimer acid is used as the b1 component (Tsunodaim 395 manufactured by Tsuno Foods Co., Ltd., C36 dicarboxylic acid content: 95%), 2-ethylhexanol is used as the c1 component, and the number of moles of hydroxyl group of a1 / carboxylic acid of b1 It charged so that ratio of mol number / hydroxyl mol number of monool might be set to 1/1 / 0.75. This was condensed using the same method as the synthesis of A-1 to obtain a complex ester A-8.
<複合エステルA−9の合成>
a1成分としてトリメチロールプロパン、b1成分としてダイマー酸(築野食品社製ツノダイム395、C36ジカルボン酸含率95%)、c1成分として2−エチルヘキサノールを用い、a1の水酸基mol数/b1のカルボン酸mol数/モノオールの水酸基mol数の比が1/2.0/1.33となるように仕込んだ。これをA−1の合成と同じ手法を用いて縮合し複合エステルA−9を得た。<Synthesis of Complex Ester A-9>
Trimethylolpropane is used as the a1 component, dimer acid is used as the b1 component (Tsunodaim 395 manufactured by Tsuno Foods Co., Ltd., C36 dicarboxylic acid content: 95%), 2-ethylhexanol is used as the c1 component, and the number of moles of hydroxyl group of a1 / carboxylic acid of b1 The mixture was prepared so that the ratio of mol number / mol number of monool hydroxyl group was 1 / 2.0 / 1.33. This was condensed using the same method as the synthesis of A-1 to obtain a complex ester A-9.
<複合エステルA−10の合成>
a1成分としてトリメチロールプロパン、b1成分としてダイマー酸(築野食品社製ツノダイム395、C36ジカルボン酸含率95%)、c1成分として2−ヘキシル−1−デカノール(日産化学社製ファインオキソコール1600)を用い、a1の水酸基mol数/b1のカルボン酸mol数/モノオールの水酸基mol数の比が1/1.57/1となるように仕込んだ。これをA−1の合成と同じ手法を用いて縮合し複合エステルA−10を得た。<Synthesis of Complex Ester A-10>
Trimethylolpropane as the a1 component, dimer acid as the b1 component (Tsunodaim 395, manufactured by Tsuno Foods Co., Ltd., 95% C36 dicarboxylic acid content), 2-hexyl-1-decanol as the c1 component (Fineoxocol 1600, manufactured by Nissan Chemical Co., Ltd.) Was added so that the ratio of mol number of hydroxyl groups of a1 / mol number of carboxylic acids of b1 / mol number of hydroxyl groups of monool was 1 / 1.57 / 1. This was condensed using the same method as the synthesis of A-1 to obtain a composite ester A-10.
<複合エステルA−11の合成>
a1成分としてトリメチロールプロパン、b1成分としてダイマー酸(築野食品社製ツノダイム395、C36ジカルボン酸含率95%)、c1成分として2−ヘキシル−1−デカノール(日産化学社製ファインオキソコール1600)を用い、a1の水酸基mol数/b1のカルボン酸mol数/モノオールの水酸基mol数の比が1/2.0/1となるように仕込んだ。これをA−1の合成と同じ手法を用いて縮合し複合エステルA−11を得た。<Synthesis of Complex Ester A-11>
Trimethylolpropane as the a1 component, dimer acid as the b1 component (Tsunodaim 395, manufactured by Tsuno Foods Co., Ltd., 95% C36 dicarboxylic acid content), 2-hexyl-1-decanol as the c1 component (Fineoxocol 1600, manufactured by Nissan Chemical Co., Ltd.) Was used so that the ratio of mol number of hydroxyl groups of a1 / mol number of carboxylic acids of b1 / mol number of hydroxyl groups of monool was 1 / 2.0 / 1. This was condensed using the same method as the synthesis of A-1 to obtain a complex ester A-11.
<複合エステルA−12の合成>
a1成分としてトリメチロールプロパン、b1成分としてダイマー酸(築野食品社製ツノダイム395、C36ジカルボン酸含率95%)、c1成分として2−ヘキシル−1−デカノール(日産化学社製ファインオキソコール1600)を用い、a1の水酸基mol数/b1のカルボン酸mol数/モノオールの水酸基mol数の比が1/1.85/1となるように仕込んだ。これをA−1の合成と同じ手法を用いて縮合し複合エステルA−12を得た。<Synthesis of Complex Ester A-12>
Trimethylolpropane as the a1 component, dimer acid as the b1 component (Tsunodaim 395, manufactured by Tsuno Foods Co., Ltd., 95% C36 dicarboxylic acid content), 2-hexyl-1-decanol as the c1 component (Fineoxocol 1600, manufactured by Nissan Chemical Co., Ltd.) Was added so that the ratio of mol number of hydroxyl groups of a1 / mol number of carboxylic acids of b1 / mol number of hydroxyl groups of monool was 1 / 1.85 / 1. This was condensed using the same method as the synthesis of A-1 to obtain a complex ester A-12.
<複合エステルA−13の合成>
a1成分としてトリメチロールプロパン、b1成分としてダイマー酸(築野食品社製ツノダイム395、C36ジカルボン酸含率95%)、c1成分として炭素数18の分岐アルキル基を有するモノアルコール(日産化学社製ファインオキソコール180N)を用い、a1の水酸基mol数/b1のカルボン酸mol数/モノオールの水酸基mol数の比が1/1.7/1となるように仕込んだ。これをA−1の合成と同じ手法を用いて縮合し複合エステルA−13を得た。<Synthesis of Complex Ester A-13>
Monoalcohol (Nissan Chemical Fine Co., Ltd.) having a trimethylolpropane as the a1 component, dimer acid as the b1 component (Tsunodaim 395 manufactured by Tsukino Foods Co., Ltd., 95% C36 dicarboxylic acid content), and a C18 branched alkyl group as the c1 component Oxocol 180N) was used so that the ratio of mol number of hydroxyl groups in a1 / mol number of carboxylic acids in b1 / mol number of hydroxyl groups in monool was 1 / 1.7 / 1. This was condensed using the same method as the synthesis of A-1 to obtain a complex ester A-13.
<複合エステルA−14の合成>
a1成分としてトリメチロールプロパン、b1成分としてダイマー酸(築野食品社製ツノダイム395、C36ジカルボン酸含率95%)、c1成分としてn−オクタデカノールを用い、a1の水酸基mol数/b1のカルボン酸mol数/モノオールの水酸基mol数の比が1/1.7/1となるように仕込んだ。これをA−1の合成と同じ手法を用いて縮合し複合エステルA−14を得た。<Synthesis of Complex Ester A-14>
Trimethylolpropane is used as the a1 component, dimer acid is used as the b1 component (Tsunodaim 395, manufactured by Tsuno Foods Co., Ltd., C36 dicarboxylic acid content: 95%), n-octadecanol is used as the c1 component, and the number of mols of hydroxyl groups in a1 / carbon of the b1 The mixture was prepared so that the ratio of mol number of acid / mol number of hydroxyl group of monool was 1 / 1.7 / 1. This was condensed using the same method as the synthesis of A-1 to obtain a complex ester A-14.
複合エステルA−1〜A−14の組成は表1の通りである。また、各成分は以下の通りである。
<a1成分>
TMP:トリメチロールプロパン
PE:ペンタエリスリトール
<b1成分>
C36−1:築野食品社製、ツノダイム395、C36ジカルボン酸含率95%
C36−2:築野食品社製、ツノダイム228、C36ジカルボン酸含率81%
C36−3:築野食品社製、ツノダイム216、C36ジカルボン酸含率79%
C36−4:水素添加されたダイマー酸(クローダ社製、プリポール1009、C36ジカルボン酸含率98%)
C44−1:C44のジカルボン酸を主成分とする重合物(クローダ社製、プリポール1004、C44ジカルボン酸含率95%)
<c1成分>
EH8B:2−エチルヘキサノール
HD16B:2−ヘキシル−1−デカノール(日産化学社製、ファインオキソコール1600)
OD18B:炭素数18の分岐アルキル基を有するモノアルコール(日産化学社製、ファインオキソコール180N)
OD18N:n−オクタデカノール
DD20B:炭素数20の分岐アルキル基を有するモノアルコール(日産化学社製、ファインオキソコール2000)The compositions of the composite esters A-1 to A-14 are as shown in Table 1. Moreover, each component is as follows.
<A1 component>
TMP: trimethylolpropane PE: pentaerythritol <b1 component>
C36-1: Tsukino Foods, Tsunodim 395, C36 dicarboxylic acid content 95%
C36-2: Tsukino Foods, Tsunodim 228, C36 dicarboxylic acid content 81%
C36-3: Tsukino Foods, Tsunodim 216, C36 dicarboxylic acid content 79%
C36-4: Hydrogenated dimer acid (manufactured by Croda, Pripol 1009, C36 dicarboxylic acid content 98%)
Polymer having C44-1: C44 dicarboxylic acid as a main component (manufactured by Croda, Pripol 1004, C44 dicarboxylic acid content 95%)
<C1 component>
EH8B: 2-ethylhexanol HD16B: 2-hexyl-1-decanol (manufactured by Nissan Chemical Industries, Fine Oxocol 1600)
OD18B: monoalcohol having a branched alkyl group having 18 carbon atoms (manufactured by Nissan Chemical Industries, Fineoxocol 180N)
OD18N: n-octadecanol DD20B: monoalcohol having a branched alkyl group having 20 carbon atoms (manufactured by Nissan Chemical Industries, Fine Oxocol 2000)
<比較用複合エステルX−1の合成>
複合エステルA−1の合成においてダイマー酸の20mol%をアジピン酸に置き換えて、a1の水酸基mol数/b1のカルボン酸mol数/モノオールの水酸基mol数の比が1/1.4/1となるように仕込んだ。これを複合エステルA−1の合成と同じ手法を用いて縮合し比較用複合エステルX−1を得た。<Synthesis of Comparative Ester X-1 for Comparison>
In the synthesis of the composite ester A-1, 20 mol% of the dimer acid was replaced with adipic acid, and the ratio of mol number of hydroxyl group of a1 / mol number of carboxylic acid of b1 / mol number of hydroxyl group of monool was 1 / 1.4 / 1. It was prepared to become. This was condensed using the same method as the synthesis of the composite ester A-1 to obtain a comparative composite ester X-1.
<比較用複合エステルX−2の合成>
a1成分としてトリメチロールプロパン、b1成分としてダイマー酸(築野食品社製ツノダイム395、C36ジカルボン酸含率95%)、c1成分として2−へキシル−1−デカノールを用い、a1の水酸基mol数/b1のカルボン酸mol数/モノオールの水酸基mol数の比が1/2.11/1.45となるように仕込んだ。これをA−1の合成と同じ手法を用いて縮合し比較用複合エステルX−2を得た。<Synthesis of Comparative Ester X-2 for Comparison>
Trimethylolpropane is used as the a1 component, dimer acid is used as the b1 component (Tsunodaim 395 manufactured by Tsukuno Foods Co., Ltd., C36 dicarboxylic acid content is 95%), 2-hexyl-1-decanol is used as the c1 component, and the number of hydroxyl groups in a1 / It charged so that ratio of mol number of carboxylic acid of b1 / mol number of hydroxyl groups of monool might be 1 / 2.11 / 1.45. This was condensed using the same method as the synthesis of A-1 to obtain a composite ester X-2 for comparison.
<比較用複合エステルX−3の合成>
a1成分としてトリメチロールプロパン、b1成分としてダイマー酸(築野食品社製ツノダイム395、C36ジカルボン酸含率95%)、c1成分として2−へキシル−1−デカノールを用い、a1の水酸基mol数/b1のカルボン酸mol数/モノオールの水酸基mol数の比が1/1.48/0.73となるように仕込んだ。これをA−1の合成と同じ手法を用いて縮合し比較用複合エステルX−3を得た。<Synthesis of Comparative Complex Ester X-3>
Trimethylolpropane is used as the a1 component, dimer acid is used as the b1 component (Tsunodaim 395 manufactured by Tsukuno Foods Co., Ltd., C36 dicarboxylic acid content is 95%), 2-hexyl-1-decanol is used as the c1 component, and the number of hydroxyl groups in a1 / It charged so that ratio of mol number of carboxylic acid of b1 / mol number of hydroxyl groups of monool might be 1 / 1.48 / 0.73. This was condensed using the same method as the synthesis of A-1 to obtain a composite ester X-3 for comparison.
<比較用複合エステルX−4の合成>
複合エステルA−1の合成においてダイマー酸の50mol%をアジピン酸に置き換えて、a1の水酸基mol数/b1のカルボン酸mol数/モノオールの水酸基mol数の比が1/0.92/1.01となるように仕込んだ。これを複合エステルA−1の合成と
同じ手法を用いて縮合し比較用複合エステルX−4を得た。<Synthesis of Comparative Ester X-4 for Comparison>
In the synthesis of the complex ester A-1, 50 mol% of dimer acid was replaced with adipic acid, and the ratio of mol number of hydroxyl group of a1 / mol number of carboxylic acid of b1 / mol number of hydroxyl group of monool was 1 / 0.92 / 1. We prepared to be 01. This was condensed using the same method as the synthesis of the composite ester A-1 to obtain a comparative composite ester X-4.
比較用複合エステルX−1〜X−4の組成は表2の通りである。 The compositions of the comparative composite esters X-1 to X-4 are as shown in Table 2.
(実施例1〜28)
表1に示す複合エステルAを基油と混合し、潤滑剤組成物を調製した。なお、基油は以下のものを用いた。
B1:鉱油(JX日鉱日石エネルギー社製、スーパーオイルN46)
40℃における動粘度46.1mm2/s
B2:ポリαオレフィン油(ANDEROL社製、ANDEROL FGC 32)40℃における動粘度32.6mm2/s
B3:エステル油(ANDEROL社製、ANDEROL 495)
40℃における動粘度28.0mm2/s
B4:B1にMoジチオカーバメートをMo含量として500ppm、ZnジチオホスフェートをZn含量として1000ppm添加した基油、40℃における動粘度46.2mm2/s(Examples 1 to 28)
The composite ester A shown in Table 1 was mixed with a base oil to prepare a lubricant composition. The following base oil was used.
B1: Mineral oil (manufactured by JX Nippon Oil & Energy, Super Oil N46)
Kinematic viscosity at 40 ° C. 46.1 mm 2 / s
B2: Poly alpha olefin oil (ANDEROL FGC 32, manufactured by ANDEROL) Kinematic viscosity at 40 ° C. 32.6 mm 2 / s
B3: Ester oil (ANDEROL 495, manufactured by ANDEROL)
Kinematic viscosity at 40 ° C. 28.0 mm 2 / s
B4: Base oil in which Mo dithiocarbamate is added to B1 at a Mo content of 500 ppm and Zn dithiophosphate is added at a ppm of 1000 ppm, kinematic viscosity at 40 ° C. 46.2 mm 2 / s
(比較例1〜8)
表1に示す複合エステルA又は表2に示す比較用複合エステルを基油と混合し、潤滑剤組成物を調製した。(Comparative Examples 1-8)
A composite ester A shown in Table 1 or a comparative composite ester shown in Table 2 was mixed with a base oil to prepare a lubricant composition.
(評価)
<摩擦係数評価>
各実施例および比較例の潤滑剤組成物について、振動型摩擦摩耗試験機(Optimol Instruments Prueftechnik GmbH社製、商品名:SRV 3)を用いて、振動数50Hz、荷重10N、振幅1mmの条件で温度40℃(条件1)と80℃(条件2)それぞれについて1時間摩擦摩耗試験を行い、時間30分おける摩擦係数を測定した。上部試験片は10mmSUJ−2ボール、下部試験片24mmSUJ−2ディスクを用いた。試験後の上部試験片を顕微鏡を用いて観測したが、ほとんど摩耗は見られず、流体潤滑領域から混合潤滑領域の摩擦挙動が観測できていると考えられる。観測した摩擦係数を以下の基準にしたがって評価した。その結果を下記表4に示した。
比較例1の条件1の摩擦係数を100%として他の評価結果を規格化、以下のように評価した。値が小さいほど摩擦係数が小さく、良好な潤滑特性であることを表す。a,bは摩擦係数が大きく低下しており、改良効果が大きいと判断した。c,dは摩擦係数の低下は見られたものの効果は小さかった、eは比較例1と比べて同等又はそれ以下で改良が見られなかったと判断した。なお、条件1及び2の試験では、b以上の評価を合格評価とした。
a:60%未満
b:60%以上70%未満
c:70%以上80%未満
d:80%以上95%未満
e:95%以上(Evaluation)
<Friction coefficient evaluation>
About the lubricant composition of each Example and Comparative Example, using a vibration type friction and wear tester (manufactured by Optimol Instruments Prutechnik GmbH, trade name: SRV 3), the temperature was set at a frequency of 50 Hz, a load of 10 N, and an amplitude of 1 mm. A friction and wear test was conducted for 1 hour at 40 ° C. (condition 1) and 80 ° C. (condition 2), and the friction coefficient at 30 minutes was measured. As the upper test piece, a 10 mm SUJ-2 ball and a lower test piece 24 mm SUJ-2 disk were used. The upper test piece after the test was observed with a microscope, but almost no wear was observed, and it is considered that the frictional behavior from the fluid lubrication region to the mixed lubrication region could be observed. The observed coefficient of friction was evaluated according to the following criteria. The results are shown in Table 4 below.
Other evaluation results were normalized by setting the friction coefficient of Condition 1 of Comparative Example 1 to 100% and evaluated as follows. The smaller the value, the smaller the coefficient of friction, indicating better lubricating properties. For a and b, the coefficient of friction was greatly reduced, and it was judged that the improvement effect was great. Although c and d showed a decrease in the friction coefficient, the effect was small, and e was judged to be equal to or less than that of Comparative Example 1 and no improvement was observed. In addition, in the test of conditions 1 and 2, evaluation more than b was set as the pass evaluation.
a: Less than 60% b: 60% or more and less than 70% c: 70% or more and less than 80% d: 80% or more and less than 95% e: 95% or more
<摩耗評価>
上記試験機にて荷重、温度を下記条件にした以外は摩擦係数試験と同じ試験を行った。<Abrasion evaluation>
The same test as the coefficient of friction test was performed except that the load and temperature were changed to the following conditions using the above tester.
試験後の上部試験片の摩耗痕を顕微鏡で観察した。比較例1の摩耗試験1で得られた摩耗痕直径を100%として規格化、以下の基準にしたがって評価した。その結果を下記表4に示した。
値が小さいほど摩耗が少ないことを表す。a〜cは摩耗痕が明らかに小さく、改良効果が大きいと判断した。dは摩耗痕は小さくなっていたものの効果は小さかった。eは比較例1の摩耗試験1と同等で改良が見られなかったと判断した。fは比較例1の摩耗試験1よりも摩耗が大きいと判断した。なお、条件3及び4の試験では、c以上の評価を合格評価とした。
a:50%未満
b:50%以上70%未満
c:70%以上85%未満
d:85%以上95%未満
e:95%以上105%未満
f:105%以上The wear mark of the upper test piece after the test was observed with a microscope. The wear scar diameter obtained in the wear test 1 of Comparative Example 1 was standardized as 100%, and evaluated according to the following criteria. The results are shown in Table 4 below.
A smaller value represents less wear. In ac, it was judged that the wear marks were clearly small and the improvement effect was large. The effect of d was small although the wear scar was small. It was judged that e was equal to the abrasion test 1 of Comparative Example 1 and no improvement was observed. f was judged to be larger than the wear test 1 of Comparative Example 1. In the tests of conditions 3 and 4, an evaluation of c or higher was regarded as a pass evaluation.
a: Less than 50% b: 50% or more and less than 70% c: 70% or more and less than 85% d: 85% or more and less than 95% e: 95% or more and less than 105% f: 105% or more
実施例及び比較例の潤滑剤組成物の組成及び評価結果を表4に示す。 Table 4 shows the compositions and evaluation results of the lubricant compositions of Examples and Comparative Examples.
表4より、実施例においては、幅広い温度範囲及び荷重条件下において優れた潤滑特性及び耐摩耗性を示していることがわかる。一方、比較例においては、潤滑特性と耐摩耗性が両立されていないことがわかる。 From Table 4, it can be seen that the examples show excellent lubricating properties and wear resistance under a wide temperature range and load conditions. On the other hand, in the comparative example, it can be seen that the lubrication characteristics and the wear resistance are not compatible.
次いで、Mobil社製のグリース(SHC Grease 460 WT)および複合エステルAをよく混合し、グリース組成物を得た。これを上述した摩耗評価と同じ手法を用いて試験を行い、以下のように評価した。なお、評価では、比較例G1の摩耗試験1で得られた摩耗痕直径を100%として規格化し、以下の基準にしたがって評価した。その結果を下記表に示した。
値が小さいほど摩耗が少ないことを表す。a〜cは摩耗痕が明らかに小さく、改良効果が大きいと判断した。dは摩耗痕は小さくなっていたものの効果は小さかった。eは比較例G1の摩耗試験1と同等で改良が見られなかったと判断した。fは比較例G1の摩耗試験1よりも摩耗が大きいと判断した。なお、条件3及び4の試験では、c以上の評価を合格評価とした。
a:50%未満
b:50%以上70%未満
c:70%以上85%未満
d:85%以上95%未満
e:95%以上105%未満
f:105%以上Next, grease (SHC Grease 460 WT) manufactured by Mobil and mixed ester A were mixed well to obtain a grease composition. This was tested using the same method as the above-described wear evaluation and evaluated as follows. In the evaluation, the wear scar diameter obtained in the wear test 1 of Comparative Example G1 was normalized as 100%, and evaluated according to the following criteria. The results are shown in the following table.
A smaller value represents less wear. In ac, it was judged that the wear marks were clearly small and the improvement effect was large. The effect of d was small although the wear scar was small. It was judged that e was equivalent to the abrasion test 1 of Comparative Example G1 and no improvement was observed. f was judged to be larger than the wear test 1 of Comparative Example G1. In the tests of conditions 3 and 4, an evaluation of c or higher was regarded as a pass evaluation.
a: Less than 50% b: 50% or more and less than 70% c: 70% or more and less than 85% d: 85% or more and less than 95% e: 95% or more and less than 105% f: 105% or more
表5より、実施例においては、幅広い温度範囲及び荷重条件下において優れた耐摩耗性を示していることがわかる。このように、本発明の潤滑剤組成物は、グリース組成物においても良好な潤滑特性をした。 From Table 5, it can be seen that the examples show excellent wear resistance under a wide temperature range and load conditions. As described above, the lubricant composition of the present invention has good lubricating properties even in the grease composition.
Claims (14)
炭素数36〜44の2価カルボン酸を少なくとも75質量%含有する、炭素数18〜22の不飽和脂肪酸の重合反応混合物、及び前記重合反応混合物を水素添加して得られた混合物、の少なくともいずれかの混合物b1、及び、
下記一般式(1)で表されるモノオールc1が縮合したポリエステルを含む複合エステルAを含有する潤滑剤組成物であって、
前記a1の水酸基mol数/前記b1のカルボン酸mol数/前記c1の水酸基mol数の仕込み比が、1/1.5〜2.0/0.7〜1.5であり、
前記複合エステルAの含有量は、前記潤滑剤組成物の全質量に対して0.1〜5質量%である潤滑剤組成物;
一般式(1):
R−OH
一般式(1)中、Rは炭素数8以上の直鎖アルキル基又は炭素数8以上の分岐アルキル基を表す。At least a trivalent or higher polyol a1,
A polymerization reaction mixture of an unsaturated fatty acid having 18 to 22 carbon atoms containing at least 75% by mass of a divalent carboxylic acid having 36 to 44 carbon atoms, and a mixture obtained by hydrogenating the polymerization reaction mixture. A mixture b1 and
A lubricant composition containing a composite ester A containing a polyester condensed with a monool c1 represented by the following general formula (1):
The charging ratio of mol number of hydroxyl groups of a1 / mol number of carboxylic acids of b1 / mol number of hydroxyl groups of c1 is 1 / 1.5 to 2.0 / 0.7 to 1.5,
The lubricant composition, wherein the content of the complex ester A is 0.1 to 5% by mass with respect to the total mass of the lubricant composition;
General formula (1):
R-OH
In general formula (1), R represents a linear alkyl group having 8 or more carbon atoms or a branched alkyl group having 8 or more carbon atoms.
前記潤滑剤組成物の全質量に対し、前記複合エステルAを0.1〜5質量%と、前記媒体を70〜99.9質量%含み、
前記潤滑剤組成物の全質量に対し、前記複合エステルA及び前記媒体以外の他の成分を0〜29.9質量%含む請求項1〜8のいずれか1項に記載の潤滑剤組成物。Further comprising a medium,
0.1-5% by mass of the composite ester A and 70-99.9% by mass of the medium with respect to the total mass of the lubricant composition,
The lubricant composition according to any one of claims 1 to 8, comprising 0 to 29.9% by mass of components other than the composite ester A and the medium with respect to the total mass of the lubricant composition.
前記複合エステルAの濃度が0.1〜5質量%である潤滑剤組成物を得る工程を含み、
前記複合エステルAを得る工程は、少なくとも、3価以上のポリオールa1、
炭素数36〜44の2価カルボン酸を少なくとも75質量%含有する、炭素数18〜22の不飽和脂肪酸の重合反応混合物、及び前記重合反応混合物を水素添加して得られた混合物、の少なくともいずれかの混合物b1、及び、
下記一般式(1)で表されるモノオールc1を、前記a1の水酸基mol数/前記b1のカルボン酸mol数/前記c1の水酸基mol数が、1/1.5〜2.0/0.7〜1.5となるように混合し、縮合させる工程である潤滑剤組成物の製造方法;
一般式(1):
R−OH
一般式(1)中、Rは炭素数8以上の直鎖アルキル基又は炭素数8以上の分岐アルキル基を表す。Obtaining composite ester A;
Including a step of obtaining a lubricant composition in which the concentration of the composite ester A is 0.1 to 5% by mass,
The step of obtaining the composite ester A includes at least a trivalent or higher polyol a1,
A polymerization reaction mixture of an unsaturated fatty acid having 18 to 22 carbon atoms containing at least 75% by mass of a divalent carboxylic acid having 36 to 44 carbon atoms, and a mixture obtained by hydrogenating the polymerization reaction mixture. A mixture b1 and
Monool c1 represented by the following general formula (1) has a molar ratio of mol of a1 / mol of carboxylic acid of b1 / mol of hydroxyl group of c1 in the range of 1 / 1.5-2.0 / 0. A method for producing a lubricant composition, which is a step of mixing and condensing so as to be 7 to 1.5;
General formula (1):
R-OH
In general formula (1), R represents a linear alkyl group having 8 or more carbon atoms or a branched alkyl group having 8 or more carbon atoms.
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CN105452327B (en) * | 2013-07-31 | 2017-06-06 | 富士胶片株式会社 | The manufacture method of complex polyester composition, lubricant compositions, lubricant and complex polyester composition |
JP6276958B2 (en) * | 2013-10-02 | 2018-02-07 | 富士フイルム株式会社 | Composite polyester composition and lubricant |
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2015
- 2015-07-24 EP EP15827870.5A patent/EP3176245B1/en active Active
- 2015-07-24 JP JP2016538323A patent/JP6348182B2/en active Active
- 2015-07-24 CN CN201580038573.6A patent/CN106661483A/en active Pending
- 2015-07-24 WO PCT/JP2015/071138 patent/WO2016017548A1/en active Application Filing
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JPS49302A (en) * | 1972-04-14 | 1974-01-05 | ||
JPS61246293A (en) * | 1985-04-03 | 1986-11-01 | Kao Corp | Cold rolling oil for steel |
JPH08176581A (en) * | 1994-12-22 | 1996-07-09 | Kobe Steel Ltd | Lubricant for low-temperature forming of aluminum and aluminum alloy plate |
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CN106661483A (en) | 2017-05-10 |
JP6348182B2 (en) | 2018-06-27 |
EP3176245A4 (en) | 2017-06-07 |
WO2016017548A1 (en) | 2016-02-04 |
US20170130160A1 (en) | 2017-05-11 |
EP3176245B1 (en) | 2019-10-30 |
EP3176245A1 (en) | 2017-06-07 |
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