CN106978231B - 含有羧酸的盐的润滑组合物 - Google Patents
含有羧酸的盐的润滑组合物 Download PDFInfo
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- CN106978231B CN106978231B CN201610898881.2A CN201610898881A CN106978231B CN 106978231 B CN106978231 B CN 106978231B CN 201610898881 A CN201610898881 A CN 201610898881A CN 106978231 B CN106978231 B CN 106978231B
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- lubricating composition
- amine
- lubricating
- fatty
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- -1 carboxylic acid compound Chemical class 0.000 claims abstract description 55
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- 239000003795 chemical substances by application Substances 0.000 claims abstract description 22
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 19
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- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
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- ZYSDERHSJJEJDS-UHFFFAOYSA-M tetrakis-decylazanium;hydroxide Chemical compound [OH-].CCCCCCCCCC[N+](CCCCCCCCCC)(CCCCCCCCCC)CCCCCCCCCC ZYSDERHSJJEJDS-UHFFFAOYSA-M 0.000 description 1
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- JVOPCCBEQRRLOJ-UHFFFAOYSA-M tetrapentylazanium;hydroxide Chemical compound [OH-].CCCCC[N+](CCCCC)(CCCCC)CCCCC JVOPCCBEQRRLOJ-UHFFFAOYSA-M 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
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- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
- C10M129/26—Carboxylic acids; Salts thereof
- C10M129/48—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring
- C10M129/54—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring containing hydroxy groups
-
- 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
- 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
- C10M129/26—Carboxylic acids; Salts thereof
- C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M129/38—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
- C10M129/44—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
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Abstract
本发明涉及含有羧酸的盐的润滑组合物。本发明提供了润滑组合物，其含有润滑粘性的油和羧酸化合物的胺或氨盐，其中所述羧酸的特征在于其被羟基取代的芳族残基官能化。本发明还涉及通过向内燃机供应所述润滑组合物来润滑内燃机的方法。本发明还涉及羧酸化合物的盐作为抗磨剂或抗氧化剂的用途。
Description
本申请是申请号为201280029312.4、申请日为2012年6月14日、发明名称为“含有羧酸的盐的润滑组合物”的申请的分案申请。
技术领域
本发明提供了润滑组合物，其含有被羟基-芳族残基取代的羧酸的盐和润滑粘性的油。本发明还涉及通过向内燃机供应所述润滑组合物来润滑内燃机的方法。本发明还涉及羧酸的盐作为抗氧化剂和/或抗磨剂的用途。
背景技术
公知的是，润滑油含有用于防止内燃机腐蚀、磨损、烟灰沉积和酸积聚的许多表面活性添加剂(包括抗磨剂、分散剂或清净剂)。这样的表面活性添加剂通常对发动机部件磨损(在铁和铝基部件中)、轴承腐蚀或燃料经济性具有有害作用。发动机润滑油的常见抗磨添加剂是二烷基二硫代磷酸锌(ZDDP)。据信，ZDDP抗磨添加剂通过在金属表面上形成保护膜来保护发动机。ZDDP还可能对燃料经济性和效率和铜腐蚀具有有害影响。因此，发动机润滑剂还可含有摩擦改进剂以消除ZDDP对燃料经济性的有害影响并含有缓蚀剂以消除ZDDP对铜腐蚀的有害影响。摩擦改进剂和其它添加剂还可能提高铅腐蚀。
此外，含有磷和硫化合物的发动机润滑剂(例如ZDDP)已表明部分造成颗粒排放和其它污染物的排放。此外，硫和磷倾向于毒化催化转化器中所用的催化剂，造成所述催化剂的性能降低。
商业上的趋势是减少排放(通常减少NOx形成、SOx形成)和减少发动机油润滑剂中的硫酸盐灰分。因此，已经降低含磷抗磨剂(例如ZDDP)、高碱性清净剂(例如钙或镁的磺酸盐和酚盐)的量。因此，已考虑无灰添加剂以提供摩擦或抗磨性能。表面活性无灰化合物(例如无灰摩擦改进剂)已知在一些情况下可增加金属(即铜或铅)的腐蚀。铜和铅腐蚀可能来自由使用铜或铅的合金制成的轴承和其它金属发动机部件。因此，需要降低由无灰添加剂造成的腐蚀量。
美国专利3,790,478公开了含有受阻酯基础油料、烷基化二苯基胺和烷基化苯基萘胺的航空燃气轮机润滑剂。该润滑剂含有0.01重量％至1重量％的C1-20烷基没食子酸酯作为铅缓蚀剂(特别提到没食子酸丙酯)。
英国专利1 358 046公开了含有0.01重量％至1重量％的C1-20烷基没食子酸酯作为铅缓蚀剂(特别提到没食子酸丙酯)的润滑剂。
英国专利GB 1 180389公开了可用于润滑喷气式飞机的发动机的合成润滑组合物。该润滑剂含有0.1重量％的没食子酸丙酯作为铅缓蚀剂。
英国专利GB 1 180 386公开了航空燃气轮机润滑剂。该润滑剂含有0.01重量％至1重量％的C1-20烷基没食子酸酯作为铅缓蚀剂(特别提到没食子酸丙酯，处理率为0.1重量％)。
英国专利GB 1 162 818公开了在航空燃气轮机中出现的极高温度下使用的合成润滑剂。该润滑剂含有0.01重量％至1重量％的C1-20烷基没食子酸酯作为铅缓蚀剂(特别提到没食子酸丙酯，处理率为0.1重量％)。
法国专利FR 2063994公开了通过添加0.2重量％至1重量％的基于(i)酯取代酚和季戊四醇亚磷酸酯-没食子酸丙酯的抗氧化剂协同混合物而抗老化的润滑剂。在实施例中以0.2重量％使用季戊四醇亚磷酸酯-没食子酸丙酯。
法国专利FR 1 537 892公开了在航空燃气轮机中出现的非常高的温度下使用的合成润滑剂。该润滑剂含有0.01重量％至1重量％的C1-20烷基没食子酸酯作为铅缓蚀剂(特别提到没食子酸丙酯，处理率为0.1重量％)。
美国专利3,336,349公开了润滑剂中的三羟基苯的酰基酯以提供热和氧化稳定性。该润滑剂可用于喷气式发动机。
美国专利7,423,000和7,582,126公开了可能含有儿茶酚化合物，如叔烷基取代的儿茶酚的组合物。
美国专利5,576,274公开了可用作分散剂和多功能粘度改进剂的燃料和润滑油添加剂，其中用烯烃聚合物将二羟基芳族化合物烷基化，然后胺化以将二羟基芳族化合物的羟基部分氧化成羰基。
美国专利2,795,548公开了含有硼酸化烷基儿茶酚的润滑油组合物的用途。该油组合物可用于内燃机曲轴箱以减轻油的氧化和发动机金属部件的腐蚀和磨损。
美国专利5,102,569公开了制备硼酸化烷基芳族多元醇的方法。该硼酸化烷基芳族多元醇可用于润滑油配方以减轻内燃机中的氧化、磨损和沉积物。
美国专利申请2006/019840公开了轴承润滑油，特别是含油烧结轴承或流体动力轴承的润滑油。该润滑油可含有没食子酸基化合物。
发明概述
本发明的发明人已经发现了一种润滑组合物，其能够提供抗磨性能、摩擦改进(特别用于增强燃料经济性)、极压性能、抗氧化性能、铅、锡或铜(通常是铅)腐蚀抑制、降低的对丙烯酸酯或含氟弹性体封条的腐蚀性或密封膨胀性能中的至少一项。
在本文中，除非另行指明，提到本文中公开的润滑组合物中存在的添加剂的量是在无油基础上引述，即基于活性剂的量。
本发明提供了润滑组合物，其包含润滑粘性的油和羧酸的胺或氨盐，其中该酸含有至少一个羰基官能团(即–COOH或-COOR)。该酸的羰基官能团的碳原子或该酸的至少一个羰基官能团的碳原子如下连接到芳族残基上：通过该羰基碳原子本身直接连接到该芳族残基的环中的碳原子上，或通过该羰基碳原子连接到烃基(即二价烃基，或亚烃基)上且该烃基连接到该芳族残基的环中的碳原子上。该芳族残基本身包括两个或更多个羟基、烷氧基或其混合物，其中这些基团连接到芳族残基中存在的环结构中的碳原子上。
本发明还提供了制造羧酸的所述胺或氨盐的方法。
本发明还提供了润滑内燃机的方法，包括步骤：(I)向内燃机供应本文所述的润滑组合物。
本发明还提供了所述羧酸的胺或氨盐的用途。
发明详述
下面通过非限制性示例描述各种优选特征和实施方案。
本发明提供了润滑组合物，其包含润滑粘性的油和含有至少一个羰基官能团的羧酸的胺或氨盐，其中该酸的羰基碳直接地或通过二价烃基键与芳族残基连接，其中所述芳族残基包括两个或更多个羟基、烷氧基、或其混合物。该胺可以是芳族或脂族的，并可以是单烷基胺、二烷基胺、三烷基胺或甚至四烷基铵。
羧酸的胺或氨盐
在一个实施方案中，本发明提供了润滑组合物，其包含润滑粘性的油和羧酸的胺或氨盐，其中所述羧酸包含式(1)的化合物：
其中a可以是2至4、或2至3、或甚至刚好2或刚好3的整数；R1可以是–C(O)OH,或–R4-C(O)OH；各R2可以独立地为氢、含有1至10个碳原子的直链或支链烃基、或其混合物；R3可以是氢或含有1至30个碳原子的烃基；R4可以是1至10个碳原子的二价烃基，包括–CH＝CH-；-C(R5)2C(R5)2-(例如-CH2CH2-)，各R5可以是氢、–CN、NH2、酯基团–C(O)O-R6、或其混合物；且R6可以是氢或含有1至30、或6至20、或8至15个碳原子的烃基。在一些实施方案中，R1和R3基团可以连接形成环，例如5元或6元环。在这些实施方案的一些中，R1和R3的连接基团可以是-O-C(＝O)-CH2CH2-或-C(＝O)-O-CH2CH2-。
在一个实施方案中，该芳族残基具有2至4个羟基、烷氧基或其混合物，其中2至3个所述羟基或烷氧基位于所述芳族残基的芳环的相邻碳原子上。基团位于芳族残基的相邻碳原子上是指，例如一个羟基连接到芳族残基中的环结构的碳原子上且第二个羟基连接到芳族残基的相同环结构中的相邻碳原子上。这两个羟基被认为彼此相邻。作为另一实例，下式(4a)中所示的两个R2O-基团被认为彼此相邻。
当式(1)两个烷氧基(-OR2)具有被定义为直链或支链烃基的R2时，合并的烃基可以是脂环族的或形成环状结构。环状结构可以由醛(例如甲醛，或其反应性对等物，例如低聚甲醛)或位于相邻碳原子上的羟基的酮桥形成。所得化合物可以由式(1a)表示：
其中R1和R2和R3如上定义；b＝0或1；且R’和R”可以独立地为氢、含有1至9个碳原子的烃基(通常R’和R”可以是氢)、或其组合。
在一个实施方案中，式(1)的芳族羧酸具有三个羟基、烷氧基或其组合(即a＝3)，以产生式(2a)或(2b)的化合物：
其中各R2独立地为氢、含有1至10个碳原子的直链或支链烃基或其混合物。
在一个实施方案中，本发明提供了润滑组合物，其包含润滑粘性的油和式(3)的羧酸化合物的胺或氨盐：
其中各R2可以独立地为氢、含有1至10个碳原子的烃基、或其混合物。
在一个实施方案中，羧酸化合物的胺或氨盐包含具有至少一个羰基官能团的羧酸化合物，其中该酸的羰基碳直接地或通过二价烃基键与芳族残基连接，其中所述芳族残基包括两个羟基、烷氧基或其混合物。
在一个实施方案中，本发明提供润滑组合物，其包含润滑粘性的油和式(4)的羧酸化合物的胺或氨盐：
其中R1、R2和R3如上定义。
在一个实施方案中，本发明提供了润滑组合物，其包含润滑粘性的油和式(4a)的羧酸化合物的胺或氨盐：
其中R2如上定义。
在一个实施方案中，本发明提供了润滑组合物，其包含润滑粘性的油和含有至少一个羰基官能团的羧酸的胺或氨盐，其中该酸的羰基碳直接地或通过二价烃基键与芳族残基连接，其中所述芳族残基包含至少两个环并包括两个或更多个羟基、烷氧基或其混合物。合适的芳族羧酸可以由式(5a)或(5b)表示：
其中R2和R3如上定义。
在一个实施方案中，上述任何式中的各R2基团可以是氢。另外，在上述任何式中，两个OR基团可以连接形成环状基团，例如5元或6元环。例如，上述任何式中的两个R2基团可以连接形成环。在一些实施方案中，在式(4a)中，R3基团与一个R2基团可以连接形成环。
在一个实施方案中，本发明的化合物可以以所述润滑组合物的0.01重量％至10重量％、0.1重量％至8重量％、0.5重量％至7重量％、或0.25重量％至2重量％存在于润滑组合物中。在一个实施方案中，本发明的成盐的酸化合物可以以该润滑组合物的0.01、0.1、0.25、0.5、1或甚至2重量％的最低量存在于润滑组合物中。在任何这些实施方案中，本发明的成盐的酸化合物可以以该润滑组合物的10、8、7、5、2或甚至1重量％的最高量存在于润滑组合物中。
在一个实施方案中，本发明的化合物可以是硼酸化或非硼酸化的。硼酸化剂是本领域中已知的，并且包括硼酸、三氧化硼或硼酸酯。硼酸化可通过式(1)的芳族羧酸的胺盐与硼酸化剂在80℃至200℃、或者100℃至160℃的反应温度下的反应进行。
在一个实施方案中，本发明的化合物(通常衍生自式(1)、(2a)、(2b)、(3)、(4)、(4a)、(5a)和/或(5b)的化合物)可以以该润滑组合物的0.01重量％至5重量％、或0.1重量％至4重量％、或0.2重量％至3重量％、或0.5重量％至2重量％存在于润滑组合物中。
在一个实施方案中，本发明的润滑组合物进一步包括抗磨剂，例如金属二烃基二硫代磷酸盐(通常为二烷基二硫代磷酸锌)，其中该金属二烃基二硫代磷酸盐为该润滑组合物提供至少100ppm、或至少200ppm、或200ppm至1000ppm、或300ppm至800ppm、或400ppm至600ppm的磷。
在一个实施方案中，本发明提供了润滑内燃机的方法，包括向内燃机供应如本文中公开的润滑组合物的步骤。通常将该润滑剂添加到内燃机的润滑系统中，其然后在运行过程中将该润滑组合物输往需要润滑的发动机关键零件。
在一个实施方案中，本发明提供了本文所述的羧酸化合物的胺(或氨)盐的用途，用作抗氧化剂、分散剂、抗磨剂、摩擦改进剂、极压剂、铅、锡或铜(通常铅)腐蚀抑制剂、降低丙烯酸酯或含氟弹性体封条的腐蚀的密封添加剂或改进密封膨胀性能的密封添加剂中的至少一项。
本发明提供了润滑组合物、如上文公开的润滑发动机的方法和如上文公开的化合物的用途。
式(1)的羧酸化合物的胺(或氨)盐可以是没食子酸、咖啡酸((3,4-二羟基)反式-肉桂酸)、(3,4,5-三羟基)反式-肉桂酸、2,5-二羟基苯甲酸、3,4-二羟基苯甲酸或其混合物的盐。式(5)的羧酸化合物的胺(或氨)盐可以是1,4-二羟基-2-萘甲酸、3,5-二羟基萘甲酸、3,7-二羟基萘甲酸或其混合物的盐。式(1)的羧酸化合物可以是三羟基化合物(即其中a＝3)。
在一个实施方案中，式(1)、(1a)、(3)、(4)、(4a)、(5a)和/或(5b)可具有被定义为氢、烷基、芳基、烷芳基、烷氧基、芳氧基或其混合物的R3。R3通常可以是氢。
在不同的实施方案中，R3可以是指含有8至18个、或5至10个碳原子的烷基。
在一个实施方案中，该羧酸可以是(多)羟基取代的芳族化合物、醚和/或烷氧基取代的芳族化合物或其组合。在不同的实施方案中，本发明的羧酸化合物包括至少两个取代基，其中该取代基是–OH、–OR或其混合物，其中R是烃基。在不同的实施方案中，R含有1至10、1至6、或1至4个碳原子。在本文所述的任何羧酸化合物内，取代基通常彼此相邻或在它们之间具有一个开放位置。例如，取代基可存在于该化合物的芳环上的1和2位、1和3位、或者1、2和3位。
在一个实施方案中，该羧酸化合物可以是含醚的芳族化合物，更具体是多醚芳族化合物。在一个实施方案中，该羧酸化合物可以是1,3-二甲氧基苯甲酸、1,3-二甲氧基苯甲酸、1,2,3-三甲氧基苯甲酸。在一个实施方案中，本发明的化合物含有两个或三个取代基，其中各取代基独立地为羟基、甲氧基、乙氧基、丙氧基、丁氧基、戊氧基、己氧基或其混合物。
包含被两个或更多个羟基或烷氧基或其混合物取代的芳族残基的羧酸的盐包括氨、伯胺、仲胺、叔胺、季铵离子或其混合物的盐。
合适的伯胺的实例包括乙胺、丙胺、丁胺、2-乙基己基胺、辛胺和十二烷基胺，以及如正辛基胺、正癸基胺、正十二烷基胺、正十四烷基胺、正十六烷基胺、正十八烷基胺和油烯胺之类的脂肪胺。其它可用的脂肪胺包括市售脂肪胺，如
胺(可获自AkzoChemicals,Chicago,Illinois的产品)，如Armeen C、Armeen O、Armeen OL、Armeen T、Armeen HT、Armeen S和Armeen SD，其中字母名称涉及脂肪基团，如椰油基、油烯基、牛脂基或硬脂基。
合适的仲胺的实例包括二甲胺、二乙胺、二丙胺、二丁胺、二戊胺、二己胺、二庚胺、甲基乙基胺、乙基丁基胺、双-2-乙基己基胺、N-甲基-1-氨基-环己烷、
2C和乙基戊基胺。该仲胺可以是环胺，如哌啶、哌嗪和吗啉。
叔胺的实例包括三-正丁基胺、三-正辛基胺、三癸基胺、三月桂基胺、三-十六烷基胺、三-2-乙基己基胺和二甲基油胺
该胺可以是通常具有叔氨基的化合物。具有叔氨基的胺包括b1-氨基哌啶、1-(2-氨基乙基)哌啶、1-(3-氨基丙基)-2-哌可啉、1-甲基-(4-甲基氨基)-哌啶、4-(1-吡咯烷基)哌啶、1-(2-氨基乙基)吡咯烷、2-(2-氨基乙基)-1-甲基吡咯烷、N,N-二乙基乙二胺、N,N-二甲基乙二胺、N,N-二丁基乙二胺、N,N-二乙基-1,3-二氨基丙烷、N,N-二甲基-1,3-二氨基丙烷、N,N,N’-三甲基乙二胺、N,N-二甲基-N’-乙基乙二胺、N,N-二乙基-N’-甲基乙二胺、N,N,N’-三乙基乙二胺、3-二甲基氨基丙基胺、3-二乙基氨基丙基胺、3-二丁基氨基丙基胺、N,N,N’-三甲基-1,3-丙烷二胺,N,N,2,2-四甲基-1,3-丙烷二胺、2-氨基-5-二乙基氨基戊烷、N,N,N’,N’-四乙基二亚乙基三胺、3,3’-二氨基-N-甲基-二丙基胺、3,3’-亚氨基双(N,N-二甲基丙基胺)或其混合物。
在一些实施方案中，该胺可以是N,N-二甲基-1,3-二氨基丙烷、N,N-二乙基-1,3-二氨基丙烷、N,N-二甲基乙二胺、N,N-二乙基乙二胺、N,N-二丁基乙二胺或其混合物。
在一个实施方案中，该胺可以是混合物形式。合适的胺混合物的实例包括(i)在叔烷基伯基团上含11至14个碳原子的胺，(ii)在叔烷基伯基团上含14至18个碳原子的胺，或(iii)在叔烷基伯基团上含18至22个碳原子的胺。叔烷基伯胺的其它实例包括叔丁胺、叔己胺、叔辛胺(如1,1-二甲基己胺)、叔癸胺(如1,1-二甲基辛胺)、叔十二烷基胺、叔十四烷基胺、叔十六烷基胺、叔十八烷基胺、叔二十四烷基胺和叔二十八烷基胺。
在一个实施方案中，可用的胺混合物包括"
81R"或"
JMT."。
81R和
JMT(都由Rohm&Haas生产和销售)分别是C11至C14叔烷基伯胺和C18至C22叔烷基伯胺的混合物。
在一个实施方案中，该胺盐可以是季铵盐形式。在美国专利3,962,104中公开了含有羟基烷基的季铵盐的实例和它们的合成方法，见第1栏第16行至第2栏第49行；第8栏第13至49行，和实施例。在某些实施方案中，该季铵化合物衍生自单胺，即只有单个氨基的叔胺，即，在这三个烃基的任一个中或与叔胺氮连接的取代烃基中没有额外的胺氮原子。在某些实施方案中，在任何烃基中或与季铵离子中的中心氮连接的取代烃基中没有额外的胺氮原子。四烷基氢氧化铵可含有具有1至30、或2至20、或3至10个碳原子的烷基。四烷基氢氧化铵可包括四丙基氢氧化铵、四丁基氢氧化铵、四戊基氢氧化铵、四己基氢氧化铵、四-(2-乙基己基)氢氧化铵、或四(癸基)氢氧化铵、或其混合物。
在经此引用并入本文的下列专利中描述了季铵盐的另一些实例和它们的制备方法：US 4,253,980、US 3,778,371、US 4,171,959、US 4,326,973、US 4,338,206和US 5,254,138。
当该胺盐衍生自芳胺时，该芳胺可以形成离子，例如吡啶鎓离子或咪唑鎓离子。
在一个实施方案中，该胺可以是含有胺官能的分散剂。这样的分散剂包括下文更详细描述的琥珀酰亚胺分散剂。
伯胺、仲胺或叔胺与羧酸的盐具有碱性和酸性；作为总碱值(TBN)和总酸值(TAN)测量这种性质。季铵(即四烷基铵)和羧酸的中性盐通常具有TBN和极小的可测TAN(通常小于5mg KOH/g，或小于1mg KOH/g，或大约0mg KOH/g)。
润滑粘性的油
该润滑组合物包含润滑粘性的油。此类油包括天然和合成油、加氢裂化、氢化和加氢精制产生的油、未精制的、精制的、再精制的油，或它们的混合物。在国际公开WO2008/147704，段落[0054]至[0056]中提供未精制的、精制的和再精制的油的更详细描述。在WO2008/147704的段落[0058]至[0059]中分别描述了天然和合成润滑油的更详细描述。也可以通过费托反应制造合成油，并通常可以是加氢异构化的费托烃或蜡。在一个实施方案中，油可以通过费托天然气合成油合成程序制备以及是其它天然气合成油。
润滑粘性的油也可以如”Appendix E-API基础油InterchangeabilityGuidelines for Passenger Car Motor Oils and Diesel Engine Oils”的2008年4月版本，第1.3节副标题1.3“Base Stock Categories”中规定的那样定义。在一个实施方案中，该润滑粘性的油可以是API第II类或第III类油。在一个实施方案中，该润滑粘性的油可以是API第I类油。
该润滑粘性的油的存在量通常是从100重量％中减去本发明的化合物和其它性能添加剂的量的总和后的余量。
该润滑组合物可以是浓缩物和/或全配方润滑剂形式。如果本发明的润滑组合物(包含本文中公开的添加剂)是浓缩物(其可以与附加的油合并以完全或部分形成成品润滑剂)形式，这些添加剂与润滑粘性的油和/或与稀释油的比率包括按重量计1:99至99:1，或按重量计80:20至10:90的范围。
其它性能添加剂
该组合物任选包含其它性能添加剂。所述其它性能添加剂包括金属钝化剂、粘度改进剂、清净剂、摩擦改进剂(非本发明的化合物)、抗磨剂(非本发明的化合物)、缓蚀剂(非本发明的化合物)、分散剂、分散剂粘度改进剂、极压剂、抗氧化剂、抑泡剂、破乳剂、倾点下降剂、密封膨胀剂及其混合物中的至少一种。通常，全配方润滑油含有这些性能添加剂中的一项或多项。
在一个实施方案中，该润滑组合物进一步包括其它添加剂。在一个实施方案中，本发明提供进一步包括分散剂、抗磨剂(非本发明的化合物)、分散剂粘度改进剂、摩擦改进剂、粘度改进剂、抗氧化剂、高碱性清净剂或其混合物中的至少一种的润滑组合物。在一个实施方案中，本发明提供进一步包括聚异丁烯琥珀酰亚胺分散剂、抗磨剂、分散剂粘度改进剂、摩擦改进剂、粘度改进剂(通常烯烃共聚物，如乙烯-丙烯共聚物)、抗氧化剂(包括酚类和胺类抗氧化剂)、高碱性清净剂(包括高碱性磺酸盐和酚盐)或其混合物中的至少一种的润滑组合物。
本发明的分散剂可以是琥珀酰亚胺分散剂或其混合物。在一个实施方案中，该分散剂可作为单一分散剂存在。在一个实施方案中，该分散剂可作为两种或三种不同分散剂的混合物存在，其中至少一种可以是琥珀酰亚胺分散剂。
琥珀酰亚胺分散剂可以是脂族多胺的衍生物或其混合物。脂族多胺可以是如亚乙基多胺、亚丙基多胺、亚丁基多胺之类的脂族多胺或其混合物。在一个实施方案中，脂族多胺可以是亚乙基多胺。在一个实施方案中，脂族多胺可选自乙二胺、二亚乙基三胺、三亚乙基四胺、四亚乙基五胺、五亚乙基六胺、多胺釜底残留物及其混合物。
分散剂可以是N-取代的长链链烯基琥珀酰亚胺。N-取代的长链链烯基琥珀酰亚胺的实例包括聚异丁烯琥珀酰亚胺。生成聚异丁烯琥珀酸酐的聚异丁烯通常具有350至5000，或550至3000，或750至2500的数均分子量。例如在美国专利3,172,892、3,219,666、3,316,177、3,340,281、3,351,552、3,381,022、3,433,744、3,444,170、3,467,668、3,501,405、3,542,680、3,576,743、3,632,511、4,234,435、Re 26,433和6,165,235、7,238,650和EP专利申请0 355 895A中公开了琥珀酰亚胺分散剂和它们的制备。
分散剂也可以通过与各种试剂反应经常规方法后处理。这些包括硼化合物、脲、硫脲、二巯基噻二唑、二硫化碳、醛、酮、羧酸、烃取代的琥珀酸酐、马来酸酐、腈、环氧化物和磷化合物。
分散剂可以以该润滑组合物的0.01重量％至20重量％、或0.1重量％至15重量％、或0.1重量％至10重量％、或1重量％至6重量％或甚至5重量％或4重量％存在。
在一个实施方案中，本发明的润滑组合物进一步包含分散剂粘度改进剂。分散剂粘度改进剂可以以该润滑组合物的0重量％至5重量％、或0重量％至4重量％、或0.05重量％至2重量％存在。
该分散剂粘度改进剂可包括官能化聚烯烃，例如，用酰化剂如马来酸酐和胺官能化的乙烯-丙烯共聚物；用胺官能化的聚甲基丙烯酸酯，或与胺反应的酯化苯乙烯-马来酸酐共聚物。在国际公开WO2006/015130或美国专利4,863,623；6,107,257；6,107,258；和6,117,825中公开了分散剂粘度改进剂的更详细描述。在一个实施方案中，该分散剂粘度改进剂可包括美国专利4,863,623(见第2栏，第15行至第3栏，第52行)或国际公开WO2006/015130(见第2页，第[0008]段，并在段落[0065]至[0073]中描述了制备例)中描述的那些。
在一个实施方案中，本发明提供进一步包括含磷抗磨剂的润滑组合物。含磷抗磨剂通常可以是二烷基二硫代磷酸锌或其混合物。二烷基二硫代磷酸锌是本领域中已知的。该抗磨剂可以以该润滑组合物的0重量％至3重量％，或0.1重量％至1.5重量％，或0.5重量％至0.9重量％存在。
在一个实施方案中，本发明提供进一步包括钼化合物的润滑组合物。该钼化合物可以选自二烷基二硫代磷酸钼、二硫代氨基甲酸钼、钼化合物的胺盐及其混合物。该钼化合物可以为该润滑组合物提供0至1000ppm、或5至1000ppm、或10至750ppm、5ppm至300ppm、或20ppm至250ppm的钼。
在一个实施方案中，本发明提供进一步包括高碱性清净剂的润滑组合物。该高碱性清净剂可选自不含硫的酚盐、含硫的酚盐、磺酸盐、salixarates、水杨酸盐及其混合物。
高碱性清净剂还可包括如例如美国专利6,429,178；6,429,179；6,153,565；和6,281,179中所述的由混合表面活性剂体系形成的“混合”清净剂，包括酚盐和/或磺酸盐组分，例如酚盐/水杨酸盐、磺酸盐/酚盐、磺酸盐/水杨酸盐、磺酸盐/酚盐/水杨酸盐。当使用例如混合磺酸盐/酚盐清净剂时，该混合清净剂被认为相当于分别引入类似量的酚盐和磺酸盐皂的单独的酚盐和磺酸盐清净剂的量。
高碱性清净剂通常可以是酚盐、含硫的酚盐、磺酸盐、salixarates和水杨酸盐的钠盐、钙盐、镁盐或其混合物。高碱性酚盐和水杨酸盐通常具有180至450TBN的总碱值。高碱性磺酸盐通常具有250至600、或300至500的总碱值。高碱性清净剂是本领域中已知的。在一个实施方案中，磺酸盐清净剂可以主要是如美国专利申请2005065045(并作为US7,407,919授权)的段落[0026]至[0037]中所述的具有至少8的金属比的直链烷基苯磺酸盐清净剂。直链烷基苯磺酸盐清净剂特别可用于辅助改进燃料经济性。直链烷基可以沿烷基的直链在任何位置连接到苯环上，但通常在直链的2、3或4位置并在一些情况下主要在2位置，从而产生直链烷基苯磺酸盐清净剂。高碱性清净剂是本领域中已知的。该高碱性清净剂可以以0重量％至15重量％、或0.1重量％至10重量％、或者0.2重量％至8重量％、或0.2重量％至3重量％存在。例如在重型柴油机中该清净剂可以以润滑组合物的2重量％至3重量％存在。对客车发动机而言，清净剂可以以润滑组合物的0.2重量％至1重量％存在。
在一个实施方案中，该润滑组合物包括抗氧化剂或其混合物。抗氧化剂可以以该润滑组合物的0重量％至15重量％、或者0.1重量％至10重量％、或0.5重量％至5重量％存在。
抗氧化剂包括硫化的烯烃、烷基化的二芳基胺(通常烷基化二苯基胺，例如二壬基二苯基胺、辛基二苯基胺、二辛基二苯基胺)、受阻酚、钼化合物(例如二硫代氨基甲酸钼)或其混合物。
受阻酚抗氧化剂通常含有仲丁基和/或叔丁基作为位阻基团。酚基团可以被连接到第二芳基上的烃基(通常直链或支链烷基)和/或桥连基团进一步取代。合适的受阻酚抗氧化剂的实例包括2,6-二-叔丁基酚、4-甲基-2,6-二-叔丁基酚、4-乙基-2,6-二-叔丁基酚、4-丙基-2,6-二-叔丁基酚或4-丁基-2,6-二-叔丁基酚，或4-十二烷基-2,6-二-叔丁基酚。在一个实施方案中，该受阻酚抗氧化剂可以是酯并可以包括例如来自Ciba的IrganoxTML-135。合适的含酯受阻酚抗氧化剂化学的更详细描述可见于美国专利6,559,105。
合适的摩擦改进剂的实例包括胺、脂肪酯或环氧化物的长链脂肪酸衍生物；脂肪咪唑啉，如羧酸和聚烯-聚胺的缩合产物；烷基磷酸的胺盐；脂肪烷基酒石酸酯；脂肪烷基酒石酰亚胺；或脂肪烷基酒石酰胺。在一些实施方案中，本文所用的术语脂肪是指具有C8-22直链烷基。
摩擦改进剂还可包括如硫化脂肪化合物和烯烃、二烷基二硫代磷酸钼、二硫代氨基甲酸钼、葵花油或多元醇与脂族羧酸的单酯之类的材料。
在一个实施方案中，该摩擦改进剂可选自胺的长链脂肪酸衍生物、长链脂肪酯或长链脂肪环氧化物；脂肪咪唑啉；烷基磷酸的胺盐；脂肪烷基酒石酸酯；脂肪烷基酒石酰亚胺；和脂肪烷基酒石酰胺。该摩擦改进剂可以以该润滑组合物的0重量％至6重量％、或0.05重量％至4重量％、或0.1重量％至2重量％存在。
在一个实施方案中，该摩擦改进剂可以是长链脂肪酸酯。在另一实施方案中，该长链脂肪酸酯可以是单酯或二酯或其混合物，在另一实施方案中，该长链脂肪酸酯可以是甘油三酯。
其它性能添加剂如缓蚀剂包括美国申请US05/038319(公开号WO2006/047486)的段落5至8中描述的那些、辛基辛酰胺、十二烯基琥珀酸或酐和脂肪酸如油酸与聚胺的缩合产物。在一个实施方案中，该缓蚀剂包括
缓蚀剂。该
缓蚀剂可以是环氧丙烷的均聚物或共聚物。在Dow Chemical Company出版的Form No.118-01453-0702AMS的产品手册中更详细描述了
缓蚀剂。产品手册的标题为“SYNALOXLubricants,High-Performance Polyglycols for Demanding Applications.”
金属钝化剂可能是有用的，包括苯并三唑衍生物(通常为甲苯基三唑)、二巯基噻二唑衍生物、1,2,4-三唑、苯并咪唑、2-烷基二硫代苯并咪唑或2-烷基二硫代苯并噻唑；抑泡剂，包括丙烯酸乙酯和丙烯酸2-乙基己酯和任选乙酸乙烯酯的共聚物；破乳剂，包括磷酸三烷基酯、聚乙二醇、聚环氧乙烷、聚环氧丙烷和(环氧乙烷-环氧丙烷)聚合物；倾点下降剂，包括马来酸酐-苯乙烯的酯、聚甲基丙烯酸酯、聚丙烯酸酯或聚丙烯酰胺。本发明的组合物中可用的抑泡剂包括丙烯酸乙酯和丙烯酸2-乙基己酯和任选乙酸乙烯酯的共聚物；破乳剂，包括磷酸三烷基酯、聚乙二醇、聚环氧乙烷、聚环氧丙烷和(环氧乙烷-环氧丙烷)聚合物。
本发明的组合物中可用的倾点下降剂包括聚α烯烃、马来酸酐-苯乙烯的酯、聚(甲基)丙烯酸酯、聚丙烯酸酯或聚丙烯酰胺。
在不同的实施方案中，该润滑组合物可具有如下表中所述的组成：
本发明的羧酸胺盐(通常衍生自式(2a)、(3)或(4))可以存在于实施方案(D)润滑组合物的0.1重量％至8重量％，或(E)润滑组合物的1重量％至7重量％，或(F)润滑组合物的2重量％至6重量％中，分散剂粘度改进剂、高碱性清净剂、抗氧化剂、抗磨剂、摩擦改进剂、粘度改进剂、任何其它性能添加剂(不包括分散剂)和润滑粘性的油的量为上表中对实施方案(A)至(C)所示的量。衍生自式(1)的本发明的化合物还可能表现出分散剂性能。如果衍生自式(1)的本发明的化合物表现出分散剂性能，实施方案(D)至(F)中引述的一部分或所有分散剂范围可以为该润滑组合物的0重量％至12重量％，或0重量％至8重量％，或0重量％至6重量％。
工业用途
该润滑组合物可用于内燃机。发动机部件可具有钢或铝表面(通常为钢表面)。
铝表面可以由铝合金构成，其可以是共晶或过共晶铝合金(例如衍生自硅酸铝、氧化铝或其它陶瓷材料的那些)。该铝表面可存在于具有铝合金或铝复合材料的缸膛、缸体或活塞环上。
该内燃机可以具有或没有废气再循环系统。该内燃机可以配有排放控制系统或涡轮增压器。该排放控制系统的实例包括柴油机微粒过滤器(DPF)或使用选择性催化还原(SCR)的系统。
在一个实施方案中，该内燃机可以是柴油机(通常重型柴油机)、汽油机、天然气发动机或混合汽油/醇发动机。在一个实施方案中，该内燃机可以是柴油机，在另一实施方案中，汽油机。
该内燃机可以是二冲程或四冲程发动机。合适的内燃机包括船用柴油机、航空活塞式发动机、低负荷柴油机、汽车和卡车发动机。
本发明的内燃机不同于燃气轮机。在内燃机中，存在独立燃烧事件，它们通过连杆和曲轴从直线往复力转换成旋转力矩。相反，在燃气轮机(也可以被称作喷气发动机)中，其是连续生成旋转力矩而不转换并且也会在排气口产生推力的连续燃烧过程。这些区别使得燃气轮机和内燃机的运行条件处于不同运行环境和应力。
该内燃机用润滑剂组合物适用于任何发动机润滑剂，与硫、磷或硫酸化灰分(ASTMD-874)含量无关。发动机油润滑剂的硫含量可以为1重量％或更低，或0.8重量％或更低，或0.5重量％或更低，或0.3重量％或更低。在一个实施方案中，硫含量可以为0.001重量％至0.5重量％，或0.01重量％至0.3重量％。磷含量可以为0.2重量％或更低，或0.12重量％或更低，或0.1重量％或更低，或0.085重量％或更低，或0.08重量％或更低，或甚至0.06重量％或更低，0.055重量％或更低，或0.05重量％或更低。在一个实施方案中，磷含量可以为100ppm至1000ppm，或200ppm至600ppm。总硫酸化灰分含量可以为2重量％或更低，或1.5重量％或更低，或1.1重量％或更低，或1重量％或更低，或0.8重量％或更低，或0.5重量％或更低，或0.4重量％或更低。在一个实施方案中，硫酸化灰分含量可以为0.05重量％至0.9重量％，或0.1重量％至0.2重量％或至0.45重量％。
在一个实施方案中，该润滑组合物是发动机油，其中该润滑组合物的特征在于具有(i)0.5重量％或更低的硫含量，(ii)0.1重量％或更低的磷含量，(iii)1.5重量％或更低的硫酸化灰分含量中的至少一项或其组合。
实施例
下列实施例例证本发明。这些实施例不是穷举的且无意限制本发明的范围。
制备例1(PE1)：没食子酸和双(2-乙基己基)胺的盐的合成。在配有顶置搅拌器、表面下气体输入管、热电偶套管、迪安斯塔克分水器和回流冷凝器的1升四颈圆底烧瓶中装入50克(0.294摩尔)没食子酸和240克二甲苯。将该烧瓶用氮气吹扫并升温至140℃。将71克双(2-乙基己基)胺(0.294摩尔)装入加料漏斗并经20分钟逐滴添加。将反应混合物搅拌并在145℃下保持7小时。将反应混合物冷却至室温并通过旋转蒸发(80℃<10Torr)除去二甲苯。产物以棕色液体(101克)形式分离。产物具有149.5mg KOH/g的通过ASTM D2896的TBN。
制备例2(PE2)：没食子酸的混合胺盐的合成。在配有顶置搅拌器、表面下气体输入管、热电偶套管、迪安斯塔克分水器和回流冷凝器的1升四颈圆底烧瓶中装入463克(1.0当量)聚异丁烯基琥珀酰亚胺(聚异丁烯2300Mn,TBN＝15mg KOH/g)并在氮气吹扫下加热至65℃。将71克双(2-乙基己基)胺(2.35当量)装入加料漏斗并将该混合物加热至100℃。将50克没食子酸(2.38当量)经10分钟逐滴添加到反应混合物中。搅拌反应混合物并在100℃下保持7小时。将反应混合物冷却至室温。产物以棕色油(566克)形式分离。产物具有39.5mgKOH/g的通过ASTM D2896的TBN。
润滑组合物
如下制备在第II类具有润滑粘性的基础油中的一系列5W-30发动机润滑剂，其含有本发明的添加剂组合物以及常规添加剂，包括聚合粘度改进剂、无灰琥珀酰亚胺分散剂、高碱性清净剂、抗氧化剂(酚酯和二芳基胺的组合)、二烷基二硫代磷酸锌(ZDDP)以及其它性能添加剂。所示量是重量百分比。
表1–润滑油组合物配方
1 酚酯和二芳基胺的混合物(1:1wt)
2 仲二烷基二硫代磷酸锌(C3-C6烷基的混合物)
3 90％油
4 常规添加剂包括聚烯琥珀酰亚胺分散剂(4重量％)、高碱性磺酸钙清净剂(1.3重量％)以及摩擦改进剂和防沫剂，各自可含有常规量的稀释剂(不单独说明)。
羧酸胺盐的磨损性能
在可获自PCS Instruments的程序升温高频往复试验机(HFRR)中评估表1中概括的润滑油组合物的边界润滑摩擦性能和磨损。该评估用的HFRR条件是500g负荷、75分钟持续时间、1000微米冲程、20赫兹频率和105℃的温度。然后测量磨损和接触电势。
也对润滑组合物施以ACEA E5氧化台架试验(CECL85)，其通过压力差示扫描量热法测定样品的氧化稳定性。作为导致油分解并开始氧化的时间(以分钟计)报道结果。
已知的是，上述一些材料可能在最终制剂中相互作用，以致最终制剂的组分可能不同于最初添加的那些。由此形成的产物，包括在其预期用途中使用本发明的润滑剂组合物时形成的产物，可能无法简单描述。无论如何，所有这样的改性和反应产物都包括在本发明的范围内；本发明包括通过混合上述组分制成的润滑剂组合物。
上文提到的各文献经此引用并入本文，如优先权文献和本申请主张其权益的所有相关申请(如果有的话)。除了在实施例中或在另行明示之处外，本说明书中指定材料量、反应条件、分子量、碳原子数等的所有数值量应被理解为用词语“大约”修饰。除非另行指明，本文提到的各化学品或组合物应被解释为是商品级材料，其可能含有异构体、副产物、衍生物和通常被理解为存在于该商品级中的其它这样的材料。但是，除非另行指明，陈述的各化学组分的量不包括商业材料中常规存在的任何溶剂或稀释油。要理解的是，本文所列的上限和下限量、范围和比率界限可以独立地组合。类似地，本发明的各要素的范围和量可以与任何其它要素的范围或量一起使用。
本文所用的术语“烃基取代基”或“烃基”以本领域技术人员公知的其普通含义使用。具体而言，其是指具有直接连接到该分子剩余部分上的碳原子并具有主要烃性质的基团。烃基的实例包括：烃取代基，包括脂族、脂环族和芳族取代基；取代烃取代基，即含有在本发明的情况下不会改变该取代基的主要烃性质的非烃基团的取代基；和杂取代基，即类似地具有主要烃性质但在环或链中含有非碳基团的取代基。在国际公开WO2008147704的段落[0118]至[0119]中描述了术语“烃基取代基”或“烃基”的更详细定义。
尽管已经联系其优选实施方案解释本发明，但要理解的是，其各种修改是本领域技术人员在阅读说明书后显而易见的。因此，要理解的是，本文公开的本发明旨在涵盖落在所附权利要求书的范围内的此类修改。
Claims (10)
1.润滑组合物，其包含润滑粘性的油和羧酸的胺或氨盐，其中所述羧酸具有式(2a)：
其中各R2独立地为氢、含有1至10个碳原子的直链或支链烃基、或者其混合物；且
R3是氢或含有1至30个碳原子的烃基，
所述润滑组合物还包含下述组分的至少之一：
(i)为总组合物提供至少100ppm磷的金属二烃基二硫代磷酸盐；
(ii)分散剂粘度改进剂，该分散剂粘度改进剂包括下述材料的至少之一：已经被酰化剂和胺官能化的乙烯-丙烯共聚物，被胺官能化的聚甲基丙烯酸酯，或与胺反应的酯化的苯乙烯-马来酸酐共聚物；或者
(iii)高碱性清净剂，该高碱性清净剂包含下述材料的至少之一：不含硫的酚盐、含硫的酚盐、磺酸盐、salixarates、水杨酸盐或其混合物。
2.权利要求1的润滑组合物，其中所述酰化剂是马来酸酐。
3.权利要求1的润滑组合物，其中R2是氢。
4.权利要求1的润滑组合物，其中所述羧酸的胺或氨盐包含羧酸的胺盐，且所述胺包含伯胺、仲胺、叔胺、季铵离子或其混合物。
5.权利要求1至4任一项的润滑组合物，其中所述盐以所述润滑组合物的0.01重量％至10重量％存在。
6.权利要求1至4任一项的润滑组合物，其中所述润滑组合物的特征在于具有(i)0.5重量％或更低的硫含量，(ii)0.1重量％或更低的磷含量，(iii)1.5重量％或更低的硫酸化灰分含量，或者它们的任何组合。
7.权利要求1至4任一项的润滑组合物，进一步包括下述材料的至少之一：抗磨剂、摩擦改进剂、粘度改进剂、抗氧化剂、或其混合物。
8.权利要求7的润滑组合物，其中所述摩擦改进剂包含下述材料的至少之一：胺的长链脂肪酸衍生物、长链脂肪酯、长链脂肪环氧化物、脂肪咪唑啉、烷基磷酸的胺盐、脂肪烷基酒石酰亚胺、脂肪烷基酒石酰胺、或其混合物。
9.权利要求7的润滑组合物，其中所述摩擦改进剂包含下述材料的至少之一：胺的长链脂肪酸衍生物、长链脂肪环氧化物、脂肪咪唑啉、烷基磷酸的胺盐、脂肪烷基酒石酸酯、脂肪烷基酒石酰亚胺、脂肪烷基酒石酰胺、或其混合物。
10.润滑内燃机的方法，包括步骤：(I)向内燃机供应权利要求1至9任一项的润滑组合物。
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| US9243202B2 (en) * | 2011-06-15 | 2016-01-26 | The Lubrizol Corporation | Lubricating composition containing a salt of a carboxylic acid |
| CN104962351A (zh) * | 2015-06-10 | 2015-10-07 | 柳州科尔特锻造机械有限公司 | 一种轮毂锻压用油的制备方法 |
| CN106635255A (zh) * | 2016-12-13 | 2017-05-10 | 中国科学院宁波材料技术与工程研究所 | 生物基油品分散剂、其制备方法及应用 |
| CN110168063A (zh) * | 2017-01-17 | 2019-08-23 | 路博润公司 | 含有聚醚化合物的发动机润滑剂 |
| KR102617908B1 (ko) * | 2017-05-31 | 2023-12-26 | 토탈에너지스 마케팅 써비씨즈 | 폴리아민, 산성 및 붕소 작용기를 포함하는 화합물 및 이의 윤활 첨가제로서의 사용 |
| EP3812363B1 (en) * | 2018-06-22 | 2022-08-03 | Panasonic Holdings Corporation | Organic salt, hydroxy-radical sensor including same, and detection medium |
| CN112585249B (zh) * | 2018-08-30 | 2022-07-08 | 巴斯夫欧洲公司 | 润滑剂组合物 |
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| US20160097018A1 (en) | 2016-04-07 |
| CN106978231A (zh) | 2017-07-25 |
| WO2012174184A1 (en) | 2012-12-20 |
| CN103597062A (zh) | 2014-02-19 |
| US20150141307A1 (en) | 2015-05-21 |
| EP2721127A1 (en) | 2014-04-23 |
| US9631159B2 (en) | 2017-04-25 |
| CN103597062B (zh) | 2016-11-09 |
| CA2836598A1 (en) | 2012-12-20 |
| US9243202B2 (en) | 2016-01-26 |
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