JP6761851B2 - 潤滑剤配合物中での摩擦調整剤としてのポリグリセロールエステルの使用 - Google Patents
潤滑剤配合物中での摩擦調整剤としてのポリグリセロールエステルの使用 Download PDFInfo
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- JP6761851B2 JP6761851B2 JP2018503570A JP2018503570A JP6761851B2 JP 6761851 B2 JP6761851 B2 JP 6761851B2 JP 2018503570 A JP2018503570 A JP 2018503570A JP 2018503570 A JP2018503570 A JP 2018503570A JP 6761851 B2 JP6761851 B2 JP 6761851B2
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- Prior art keywords
- acid
- lubricating oil
- oil composition
- composition according
- polyglycerol
- Prior art date
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- 238000009472 formulation Methods 0.000 title description 7
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- 235000021357 Behenic acid Nutrition 0.000 claims description 2
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims description 2
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- 229940108623 eicosenoic acid Drugs 0.000 claims description 2
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- 239000001530 fumaric acid Substances 0.000 claims description 2
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- NNNVXFKZMRGJPM-KHPPLWFESA-N sapienic acid Chemical compound CCCCCCCCC\C=C/CCCCC(O)=O NNNVXFKZMRGJPM-KHPPLWFESA-N 0.000 claims description 2
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
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- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
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- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
- C10M169/044—Mixtures of base-materials and additives the additives being a mixture of non-macromolecular and macromolecular compounds
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- C10M2203/102—Aliphatic fractions
- C10M2203/1025—Aliphatic fractions used as base material
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- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
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- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
- C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/04—Molecular weight; Molecular weight distribution
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/02—Pour-point; Viscosity index
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
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- C—CHEMISTRY; METALLURGY
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
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- Chemical Kinetics & Catalysis (AREA)
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- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Lubricants (AREA)
Description
(i)多官能性カルボン酸および
(ii)飽和もしくは不飽和の直鎖状もしくは分枝鎖状の脂肪酸および/または
(ii)ポリ(ヒドロキシステアリン酸)
でエステル化することによって得られることを特徴とする。
(a)90〜100重量%のAPIグループII、IIIおよびIVからなる群から選択される非極性油ならびに/またはそれらの混合物と、
(b)0〜10重量%の米国石油協会(API)の定義に従ったグループVの極性エステル油と
を含むことを特徴とする。
HLB=(mp/(mp+ma))*20、
ここで、mpは、ポリグリセロールの質量であり、maは、ポリグリセロールエステルの合成において使用されるモノ−、ジ−およびポリカルボン酸のほかにポリヒドロキシ脂肪酸を含むカルボン酸混合物の質量である。例えば、100gのポリグリセロールを90gのモノカルボン酸および10gのジカルボン酸とでエステル化した場合、ポリグリセロールの重合度および使用されるカルボン酸の種類とは無関係に、(100g/(90g+10g+100g))*20=10のHLBが得られる。
(a)潤滑油組成物の全重量に対して0.2〜5重量%、好ましくは0.3〜3重量%、さらにより好ましくは0.5〜2重量%のポリグリセロール部分エステルと、
(b)潤滑油組成物の全重量に対して85〜99.8重量%、好ましくは87〜99.7重量%、さらにより好ましくは88〜99.5重量%のAPIグループII、IIIおよびIVからなる群から選択される非極性ベースストックならびに/またはそれらの混合物と、
(c)潤滑油組成物の全重量に対して0〜10重量%の米国石油協会(API)の定義に従ったグループVの極性エステル油と
を含む潤滑油組成物に関する。
実施例1:欧州特許第1500427号明細書(EP1 500 427 B1)の合成例2に従ったポリグリセロール、イソステアリン酸、セバシン酸およびポリ(ヒドロキシステアリン酸)から調製されたポリカルボン酸エステル
イソステアリン酸(91.1g、0.320mol)とポリ(ヒドロキシステアリン酸)(141.7g、0.120mol、酸価47mgKOH/g)との混合物を、窒素流通下でポリグリセロール(61.9g、0.121mol、ヒドロキシル価950mgKOH/g)を用いて240℃でエステル化した。この温度で2時間後、反応混合物の酸価は、10未満であった。次いで、混合物を130℃に冷却し、セバシン酸(20.2g、0.100mol)を添加し、混合物を240℃に再び加熱した。この温度で3時間後、5未満の酸価を有する粘性生成物を得た。
オキシラン[O]含有率6.3%のエポキシ化大豆油(300g、0.302mol)、オレイン酸(331g、1.18mol)および二量体酸(57.5g;0.101mol、約2%の一塩基酸、約96%の二量体酸および約2%の三量体酸および高級ポリ酸を含む)の混合物を、酸価が10mgKOH/g未満になるまで240℃に加熱した。
このポリマーの構造は、本発明によるポリグリセロール部分エステルとは異なり、したがって、本発明には包含されない。
イソステアリン酸72gとセバシン酸11gとの混合物を、窒素流通下で17gのポリグリセロール(平均重合度=3)と240℃でエステル化した。12の酸価に達したら、反応を冷却した。
このポリマーのOH価は、本発明による好適な範囲よりもはるかに低い。
ポリマー摩擦調整剤Perfad(商標)3006であって、これは、Croda Inc.から市販されている(構造については米国特許出願公開第2013/0079536号明細書(US 2013/0079536)、国際公開第2011/107739号(WO 2011/107739 A1)および物理的性質についてはLube Magazine No.120,April 2014,page 27を参照)。
このポリマーの構造は、本発明によるポリグリセロール部分エステルとは異なり、したがって、本発明には包含されない。
Perfad(商標)3050の希釈形態である、ポリマー摩擦調整剤Perfad(商標)3057であって、これは、Croda Sucursal Colombiaから市販されている(構造については米国特許出願公開第2013/0079536号明細書(US 2013/0079536)、国際公開第2011/107739号(WO 2011/107739 A1)および物理的性質についてはLube Magazine No.120,April 2014,page 27を参照)。
このポリマーの構造は、本発明によるポリグリセロール部分エステルとは異なり、したがって、本発明には包含されない。
*)Perfad(商標)3050の所与の値;Perfad(商標)3057は、Perfad(商標)3050の希釈形態である。
100℃での摩擦係数の測定は、PCS Instrumentsのミニトラクションマシン(MTM)で行った。この試験は、スチールボールとスチールディスクによって形成される潤滑接触部において生じる摩擦レベルを評価することからなる。ボールとディスクの速度は、独立して設定される。ボールは、スチールディスクに対して転がり滑り状態で負荷および摩擦され、接触部は、完全に油に浸漬される。
次いで、第3表に示す条件下で摩擦係数を測定することによってストライベックを得た。
台形公式を使用した滑り速度0.005〜2.5m/sの範囲における摩擦値曲線の積分。この面積は、試験した全速度範囲にわたる「全摩擦」に対応している。面積が小さいほど、試験したポリマーの摩擦低減効果は大きくなる。
Claims (13)
- 潤滑油組成物であって、
(a)前記潤滑油組成物の全重量に対して0.2〜5重量%のポリグリセロール部分エステルと、
(b)前記潤滑油組成物の全重量に対して85〜99.8重量%のAPIグループII、IIIおよびIVからなる群から選択される非極性ベースストックならびに/またはそれらの混合物と、
(c)前記潤滑油組成物の全重量に対して0〜10重量%の米国石油協会(API)の定義に従ったグループVの極性エステル油と
を含み、前記ポリグリセロール部分エステルは、ポリグリセロール混合物を、
(i)多官能性カルボン酸および
(ii)飽和もしくは不飽和の直鎖状もしくは分枝鎖状の脂肪酸および
(iii)ポリ(ヒドロキシステアリン酸)
でエステル化することによって得られることを特徴とし、ここで、前記多官能性カルボン酸(i)が、マロン酸、コハク酸、フマル酸、マレイン酸、ジメチルグルタル酸、アジピン酸、トリメチルアジピン酸、アゼライン酸、セバシン酸、ドデカン二酸およびそれらの無水物からなる群から選択される脂肪族ジカルボン酸であり、かつ前記ポリグリセロール部分エステルが、110〜150mgKOH/gの範囲のOH価を有することを特徴とする、潤滑油組成物。 - 前記ポリグリセロール混合物が、3〜6の平均縮合度を有することを特徴とする、請求項1記載の潤滑油組成物。
- 前記飽和または不飽和の直鎖状または分枝鎖状の脂肪酸が、8〜22個の炭素原子を有することを特徴とする、請求項1または2記載の潤滑油組成物。
- 前記飽和または不飽和の直鎖状または分枝鎖状の脂肪酸が、12〜18個の炭素原子を有することを特徴とする、請求項1または2記載の潤滑油組成物。
- 前記飽和脂肪酸が、カプリル酸、カプリン酸、ラウリン酸、トリデカン酸、ミリスチン酸、パルミチン酸、マルガリン酸、ステアリン酸、イソステアリン酸、アラキジン酸、ベヘン酸、12−ヒドロキシステアリン酸およびそれらの混合物からなる群から選択される、請求項1、2、3または4記載の潤滑油組成物。
- 前記不飽和脂肪酸が、ヘキサデセン酸、オクタデセン酸、エイコセン酸、ドコセン酸、オクタデカジエン酸、オクタデカトリエン酸、リシノール酸およびそれらの混合物からなる群から選択されることを特徴とする、請求項1、2、3、4または5記載の潤滑油組成物。
- 前記ポリグリセロール部分エステルが、3〜7のHLB値を有することを特徴とする、請求項1、2、3、4、5または6記載の潤滑油組成物。
- 1種以上の更なる添加剤を追加で含むことを特徴とする、請求項1、2、3、4、5、6または7記載の潤滑油組成物。
- 前記1種以上の更なる添加剤が、粘度指数(VI)向上剤、流動点降下剤、分散剤、清浄剤、消泡剤、腐食防止剤、酸化防止剤、耐摩耗添加剤および極圧添加剤および摩擦調整剤からなる群から選択されることを特徴とする、請求項8記載の潤滑油組成物。
- 前記ポリグリセロール部分エステルが、2000〜15000g/molの重量平均分子量を有することを特徴とする、請求項1、2、3、4、5、6、7、8または9記載の潤滑油組成物。
- 前記ポリグリセロール部分エステルが、4000〜10000g/molの重量平均分子量を有することを特徴とする、請求項1、2、3、4、5、6、7、8または9記載の潤滑油組成物。
- 請求項1から11までのいずれか1項記載の潤滑油組成物を使用してエンジンを潤滑させる方法。
- 請求項1から11までのいずれか1項記載の潤滑油組成物を適用することによってエンジン内の摩擦を低減させる方法。
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PCT/EP2016/065904 WO2017016825A1 (en) | 2015-07-24 | 2016-07-06 | Use of polyclycerin esters as friction modifiers in lubricant formulations |
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WO2018033259A1 (de) | 2016-08-18 | 2018-02-22 | Evonik Degussa Gmbh | Vernetzte polyglycerinester |
DE102017009541A1 (de) | 2017-10-13 | 2019-04-18 | Daimler Ag | Ventiltrieb für eine Brennkraftmaschine eines Kraftfahrzeugs |
WO2020152286A2 (de) * | 2019-01-23 | 2020-07-30 | Peter Greven GmbH & Co. KG | Estolidester und ihre verwendung als basisöl in schmierstoffen |
TWI793346B (zh) * | 2019-07-10 | 2023-02-21 | 百達精密化學股份有限公司 | 液態有機磨耗改進劑 |
JP2022158116A (ja) * | 2021-04-01 | 2022-10-17 | Eneos株式会社 | 潤滑油組成物 |
CN113512460B (zh) * | 2021-08-13 | 2022-10-21 | 福建科恩优路润滑油有限公司 | 抗磨清洁型车用润滑油及其制备工艺 |
CN113801310B (zh) * | 2021-09-24 | 2023-03-21 | 广东产品质量监督检验研究院(国家质量技术监督局广州电气安全检验所、广东省试验认证研究院、华安实验室) | 一种三组分催化引发体系催化剂及其应用 |
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JPS53102307A (en) * | 1977-02-18 | 1978-09-06 | Nippon Oil & Fats Co Ltd | Lubricating oil composition |
US4153464A (en) * | 1977-09-12 | 1979-05-08 | Emery Industries, Inc. | Prevention of water staining of aluminum |
JP2579502B2 (ja) * | 1987-11-26 | 1997-02-05 | 日清製油株式会社 | 潤滑油 |
CA2170503C (en) * | 1994-07-05 | 2005-08-16 | Noriyoshi Tanaka | Engine oil composition |
DE4444137A1 (de) * | 1994-12-12 | 1996-06-13 | Henkel Kgaa | Synthetische Ester aus Alkoholen und Fettsäuregemischen aus ölsäurereichen, stearinsäurearmen Pflanzenölen |
US5698502A (en) * | 1996-09-11 | 1997-12-16 | Exxon Chemical Patents Inc | Polyol ester compositions with unconverted hydroxyl groups for use as lubricant base stocks |
DE19641604C1 (de) * | 1996-10-09 | 1998-03-12 | Goldschmidt Ag Th | Polyglycerinpartialester von Fettsäuren und mehrfunktionellen Carbonsäuren, deren Herstellung und Verwendung |
EP0903399B1 (de) * | 1997-09-18 | 2007-02-14 | Ciba SC Holding AG | Schmierstoffzusammensetzungen mit Thiophosphorsäureestern und Dithiophosphorsäureestern |
DE10333443A1 (de) * | 2003-07-23 | 2005-02-10 | Goldschmidt Ag | Emulgator für dünnflüssige W/O-Emulsionen auf Basis von teilvernetzten Polyglycerinestern der Polyhydroxystearinsäure |
EP2036963A1 (de) * | 2007-09-14 | 2009-03-18 | Cognis Oleochemicals GmbH | Schmiermitteladditive für Bohrspülmittel |
WO2010053893A1 (en) * | 2008-11-05 | 2010-05-14 | The Lubrizol Corporation | Method of lubricating an internal combustion engine |
EP2345710A1 (en) * | 2010-01-18 | 2011-07-20 | Cognis IP Management GmbH | Lubricant with enhanced energy efficiency |
WO2011161406A1 (en) * | 2010-06-25 | 2011-12-29 | Castrol Limited | Uses and compositions |
GB201317278D0 (en) * | 2013-09-30 | 2013-11-13 | Croda Int Plc | Gear oil composition |
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CA2993333A1 (en) | 2017-02-02 |
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