CN1220687A - 用于燃料和润滑剂的减小摩擦添加剂 - Google Patents

用于燃料和润滑剂的减小摩擦添加剂 Download PDF

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CN1220687A
CN1220687A CN199898800257A CN98800257A CN1220687A CN 1220687 A CN1220687 A CN 1220687A CN 199898800257 A CN199898800257 A CN 199898800257A CN 98800257 A CN98800257 A CN 98800257A CN 1220687 A CN1220687 A CN 1220687A
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alkyl
fuel
alkylidene group
product
lubricant compositions
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CN1095872C (zh
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J·T·凯里
H·奥马-穆罕默德
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ExxonMobil Oil Corp
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Mobil Oil Corp
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Abstract

本发明提供了特定的羟基乙酰胺,它是通过伯醚胺和羟基羧酸的反应制得的,特别是乙醚胺2-羟乙酰胺,以及将它们用作燃料和润滑剂中的减小摩擦添加剂。

Description

用于燃料和润滑剂的减小摩擦添加剂
本发明涉及伯醚胺与羟基羧酸(hydroxycarboxylic acid)反应形成羟基酰胺,以及使用所得产物作为燃料和润滑剂中的减小摩擦添加剂。本发明更具体的是涉及含有该减小摩擦添加剂的燃料和润滑剂的组合物和提浓物(concentrates)。
当今人们所关注的主要问题是寻求减小发动机摩擦和降低内燃机中燃料消耗的方法,这些方法是对环境无害的且是经济的。一种方法是用含有减小摩擦添加剂的润滑剂处理这些发动机的活动部件。在这一领域中人们作了大量的工作。
美国专利No.4,617,026中揭示了将三元醇的一羧酸酯,即单油酸甘油酯用作燃料和润滑剂中的减小摩擦添加剂,以提高内燃机中的燃料经济使用。
美国专利Nos.4,789,493,4,808,196和4,867,752中揭示了使用脂族甲酰胺。
美国专利No.4,280,916中揭示了使用脂肪酸酰胺。
美国专利No.4,406,803中揭示了在润滑剂中使用烷烃-1,2-二醇来提高内燃机的燃料经济使用。
美国专利No.4,512,903揭示了由单羟基或多羟基取代的脂族一羧酸和伯胺或仲胺制得的酰胺类,它可用作减小摩擦剂。
因此,本发明的一个目的是提供一种用于减小和/或防止摩擦的组合物。
本发明的另一个目的是提供一种用于减小内燃机运转中摩擦的方法。
本发明涉及N-烷氧基-烷基-羟基乙酰胺,它通过伯醚胺(primary etheramines)和羟基羧酸的缩合反应制得,是用于燃料(特别是汽油)、燃料添加剂提浓物、润滑剂和润滑添加剂提浓物的有效的减少摩擦添加剂,并具有高温下分解的清洁度。
本发明提供了一种润滑剂组合物,它包含润滑油或由其制得的润滑脂(grease),以及减小摩擦量的非硼酸化的反应产物(non-borated reaction product),该反应产物是通过R1(OR2)aNH2和羟基羧酸反应制得的,其中R1是烃基或C1-C60烷基,R2是C1-C4亚烷基,a是1至12。
本发明还提供了一种燃料组合物,它包括内燃机燃料和减小摩擦量的非硼酸化的产物,该产物是通过R1(OR2)aNH2和羟基羧酸反应得到的,其中R1是烃基或C1-C60烷基,R2是C1-C4亚烷基,a是1至12。
本发明还提供了一种用于减小和/或防止内燃机运转中摩擦的方法,它包括向所述发动机中加入液态燃料组合物,该组合物包括每1000桶燃料25至250磅的非硼酸化的产物,该产物是通过R1(OR2)aNH2和羟基羧酸反应得到的,其中R1是烃基或C1-C60烷基,R2是C1-C4亚烷基,a是1至12。
已发现,羟基羧酸和伯醚胺的反应产物具有优良的减小摩擦的性能和优良的高温清洁度和分解性能,这些性能是用于内燃机的优质燃料和润滑剂所必需的。这些化合物如下制备:将各种伯醚胺和羟基羧酸在回流下进行缩合反应,回流温度高至足以将最初形成的铵盐转化为酰胺。
在N-烷氧基-烷基-羟基乙酰胺的制备中所用的伯醚胺是如下化学式的伯醚胺:
           R1(OR2)aNH2其中R1是C1-C60烷基,通常是C4-C20烷基,可任选的具有取代基,如芳基、烷芳基;R2是C1-C4亚烷基;a是1至12,通常为1至4。
合适的伯醚胺包括C6-C12烷氧基丙胺或其混合物。较好的醚胺是C6-C12烷氧基丙胺的混合物。使用醚胺的优点包括低温流动性和清洁度。
此外,伯醚胺可以与烷基胺结合使用。合适的烷基胺包括纯的饱和或不饱和的一元胺和/或二元胺,或者由脂肪酸(如椰子(coco)、油(oleyl)或动物脂(tallow))衍生得到的烷基胺的混合物。
伯醚胺和烷基胺在其烷基链上也可以含有杂原子,如氧、硫或氮。胺上的烷基链足够长以提供减小摩擦的性能,但不能太长以致于不能防止长链烷烃的固有蜡质。然而,可以通过向烷基链中引入不饱和部位或杂原子来将蜡质减至最小。
合适的羟基羧酸包括α-羟基羧酸,如乙醇酸(羟基乙酸)和乳酸(α-羟基丙酸),以及二羟烷基羧酸,如2,2-二羟烷基丙酸(尤其是2,2-二羟甲基丙酸)。较好的是乙醇酸。
所用的酸可以是纯的或者是在溶液中。例如,乙醇酸可以是纯固体或者是浓度为70%的水溶液。乳酸可以是浓度为85%的水溶液。在溶液的情况下,在为了决定完全反应而计算水的摩尔数时应该扣除过量的水。
烃类溶剂或其它惰性溶剂可以用于反应中。在可用的溶剂中有苯、甲苯和二甲苯。当使用溶剂时,较好的溶剂是二甲苯。一般来说,可以使用任何能够溶解反应剂和产物并且易于除去的烃类溶剂。
可以用脱湿器(moisture trap)(Dean-Stark仪器)进行溶剂与反应过程中所形成水的恒定的共沸除去。在一些情况下,可以用连续加热来汽提除去溶剂,在除去预计量的水之后通过施加低真空(10-20mm/Hg)来完全地除去溶剂。在其它情况下,溶剂可以保留在最终混合物中以提供该混合物的流动性。
缩合反应通常如下进行:
R1(OR2)aNH2+HOCOR3OH    R1(OR2)aNHCOR3OH
其中,R1是烃基,C1-C60烷基(可任选的含有硫、氧和/或氮)、芳基、烷芳基、环烷基、较好的是C4-C20,具有可任选的取代基,如芳基、烷芳基、环烷基;R2是C1-C4亚烷基;R3是C1-C4亚烷基或被取代的亚烷基、芳基、烷芳基或环烷基;a是1至12,通常为1至4。
反应温度通常在100℃至175℃的范围内,较好的在145℃至165℃的范围内。反应时间通常为3至24小时,较好的为4至8小时。
较好的是使用化学计算量的胺和酸。然而,一种或另一种反应剂过量是较好的。
润滑剂组合物中的减小摩擦添加剂的含量可以是润滑剂组合物总量的0.1-10%(重量)。较好的是0.1-2.0%(重量)。
在润滑添加剂提浓物中,减小摩擦添加剂的量可以是润滑添加剂提浓物总量的1.0-50.0%(重量)。较好的是10-30%(重量)。
润滑剂组合物和/或润滑添加剂提浓物可以含有添加剂包装(additive packages)中常见的其它物质,如分散剂、洗涤剂、抗氧剂、抗磨剂和耐特压剂、粘度指数改善剂、防腐蚀剂、防锈剂、防泡沫剂、倾点下降剂、各种标记剂(markers)、标签剂(taggants)和任何增溶剂,如油类、聚合物、溶剂等。这些物质将它们的常见性能赋予特定的组合物,并不减损它们所加入的组合物的价值。
合适的分散剂包括聚亚烷基琥珀酰亚胺、曼尼期碱、聚醚、聚亚烷基胺、各种酯等。
合适的洗涤剂包括金属和/或非金属的酚盐、磺酸盐、羧酸盐等。
合适的抗氧剂包括受阻酚、芳化胺、硫化烯烃等。
合适的粘度指数改善剂包括聚甲基丙烯酸酯、烯烃共聚物等。
合适的抗磨剂和耐特压剂包括二硫代磷酸二烷酯锌盐、二硫代氨基甲酸盐(酯)、噻二唑等(zinc dialkyl dithiophosphates,dithiocarbamates,thiodiazoles)。
一般来说,所有这些其它物质的总量不能超过润滑剂组合物的10.0-30.0%(重量),不能超过润滑添加剂提浓物的10.0-100.0%(重量)。
而且,要用于本发明的润滑剂包括具有润滑粘度的矿物烃类油和合成烃类油、矿物油和合成油的混合物以及由其制得的润滑脂,以及其它固态润滑剂。合成油可以包括聚α-烯烃;聚亚烷基二醇,如聚丙二醇、聚乙二醇、聚丁二醇;酯,如癸二酸二(2-乙基己基)酯、邻苯二甲酸二丁酯、新戊酯(如季戊四醇酯)、三羟甲基丙酯;聚异丁烯;聚苯;醚,如苯氧基苯基醚;碳氟化合物;硅氧烷;聚硅氧烷;硅烷和硅酸酯;氢化矿物油,或者它们的混合物。
本发明还可用于燃料,如汽油、加氧汽油、重整汽油、酒精汽油、烃类燃料、烃类燃料和加氧燃料的混合燃料、喷射式涡轮发动机燃料和柴油机燃料。本发明还可用于燃料添加剂提浓物。
燃料组合物可以含有每1,000桶燃料10至1,000磅减小摩擦添加剂,或者较好的是每1,000桶燃料25至250磅。
在燃料添加剂提浓物中,减小摩擦添加剂的量可以在燃料添加剂提浓物重量的1.0%-50.0%(重量)的范围内。较好的是10%-30%(重量)。
燃料和燃料添加剂提浓物可以含有燃料添加剂包装中常见的其它物质,包括用于化油器、出入口燃料注入/喷射器(port fuel injecotors)、进气口、进气阀和燃烧室的控制沉积添加剂;载体流体;抗爆剂(如四烷基铅化合物、有机锰化合物、铅净化剂、辛烷增强添加剂等);染料;标记剂;标签剂;十六烷值增进剂(如硝酸烷基酯、烷基过氧化物等);抗氧剂(如受阻酚、芳化胺、硫化烯烃等);防锈剂;反乳化剂;抑菌剂;阻胶剂;防冻剂;金属减活化剂;排气阀抗衰退剂(exhaust valveanti-recession agent);火花增强添加剂;低温增溶剂;低温性能所必需的溶剂,或者它们的混合物。
合适的反乳化剂包括烷氧化的烷基酚醛(甲醛)树脂和聚氧化烯基二醇。
合适的载体流体包括矿物油和/或合成油、聚亚烷基类、酯、多元醇、聚醚,或者它们的混合物。
合适的防腐蚀剂包括丁二酸烷基乳基酯(alkyl lactic succinate esters)。
燃料和燃料添加剂提浓物通常包括有效量的至少一种洗涤剂。该洗涤剂通常选自聚亚烷基胺,以及烃基酚类、醛类和胺类的曼尼期碱型缩合产物。这些洗涤剂通常能减少和/或防止在化油器、燃料喷射系统中往往会形成的沉积,从而提高发动机性能。这些洗涤剂还能提高燃料的经济使用,并且减少内燃机的废气排放。
较好的聚亚烷基胺洗涤剂选自聚合的1-胺,包括聚异丁烯胺(polyisobutylene-amines)。最好的是高乙烯含量的聚异丁烯胺。在美国专利Nos.5,004,478和5,112,364,以及DE3942860中记述了合适的聚异丁烯胺,这些说明全部结合参考于本发明中。较好的聚异丁烯胺的平均分子量是500至3,000或更大。
这些聚亚烷基胺通常可以从市场上购得,或者可以由平均分子量为500至3000或更大的高乙烯含量的聚烯烃的胺化作用制得,制备方法是本领域技术人员已知的。聚异丁烯胺的制备通常如下:对反应性聚异丁烯进行氯化或加氢醛化,接着用氨、烃基胺、烃基二胺、烃基多胺、烷氧基化的烃基胺,或者它们的混合物进行胺化作用。可以向聚烯烃胺(polyalkeneamines)中混入氨、1,2-乙二胺、二亚乙基三胺、三亚乙基四胺、四亚乙基五胺、哌嗪、己二胺、羟烷基乙二胺、羟烷基三亚乙基四胺等。这些胺可以如下制备:对适宜的聚合烯烃进行氯化或卤化,接着用种种已知的制备方法将它们转化成相应的聚烯烃衍生物。
燃料组合物中聚亚烷基胺的含量可以是每1,000桶燃料至少10至200磅,较好的是每1,000桶燃料至少40至150磅。
燃料添加剂提浓物中聚亚烷基胺的含量可以是至少为10%(重量),较好的是至少20%(重量),最好的是在25-60%(重量)的范围内。
此外,较好的洗涤剂是烃基酚类、醛类和胺类的曼尼期碱缩合产物。烃取代的酚类通常制备如下:用含10至150碳原子的烃基对苯酚或酚进行烷基化作用。例如,长链烯烃或聚合烯烃(如丙烯和聚异丁烯)可用于酚的烷基化步骤。然后,将被取代的酚与羰基源和胺反应。羰基源包括醛类,如甲醛、乙醛、丙醛、丁醛和2-乙基己醛。此外,芳族醛类可用于提供羰基源。例如,可以使用苯甲醛、甲苯甲醛、香草醛、水杨醛和肉桂醛。聚羰基化合物(如多聚甲醛和乙二醛)也可用于本发明的一些方面。
用于制备曼尼期碱缩合产物的胺包括伯胺或仲胺和酰胺。脂族胺、含羟基的胺或多胺(如二胺、三胺、四胺和五胺)可用于本发明的一些方面。例如,可以使用直链或环状的C2-C6亚烷基二胺、三胺、四胺和五胺、多胺,以及它们的被取代的多官能的衍生物。此处所用的“被取代的衍生物”是指用取代基取代,这些取代基例如卤、羟基、烷氧基、硝基、硫基、烷氧羰基和烷硫基。这些曼尼期碱缩合产物通常可从市场上购得。合适的曼尼期碱缩合产物记述于美国专利No.5,169,410中,该记述内容全部结合参考于本发明中。
在燃料组合物中曼尼期碱缩合产物的含量可以是每1,000桶燃料至少10至200磅,较好的是每1,000桶燃料至少40至150磅。
在燃料添加剂提浓物中曼尼期碱缩合产物的含量可以是至少10%(重量),较好的是至少20%(重量),最好的是25-60%(重量)的范围内。
使用了本发明减小摩擦添加剂的提浓物中通常还包括15-80%的溶剂。较好的组成范围如下:组分       重量%范围羟基乙酰胺    5-25洗涤剂       20-60溶剂异丙醇        0-30二甲苯       15-50
在现描述的本发明用作汽油添加剂的情况下,添加剂包装可以在提炼汽油之后的任何时间地点加入,也就是说添加剂包装可以在炼油厂或在配送体系中加入。
本发明还包括一种减小和/或防止内燃机运转中摩擦的方法。本发明可实现的其它可能的益处包括提高了发动机清洁度、提高了润滑性、提高了耐腐蚀性能、降低了燃料消耗、提高了功率,以及降低了磨损。该方法包括向内燃机中加入一种燃料,该燃料如上所述包括汽油和减小摩擦添加剂,以及其它常见于添加剂包装中的物质。
以下实施例是对本发明的说明。
实施例1
将400克(2.0摩尔)经蒸馏的脂族椰子胺(fatty cocoamine)(Armed CD,购自Kazoo Chemicals,Inc.)和152.0克(2.0摩尔的纯粉末)的乙醇酸(购自AldrichChemical Co.)在500毫升二甲苯溶剂中的溶液在惰性氮气气氛下于回流下(140℃)加热3个小时。用脱湿器通过与二甲苯的共沸蒸馏恒定地除去反应过程中形成的水。然后将该溶剂在高至160℃的温度下蒸馏汽提20分钟,接着在10-20mm/Hg的减压下于140℃蒸馏汽提45分钟。得到580克白色蜡质固体。
实施例2
将414克(2.0摩尔)乙醚胺(etheramine)、C8-C10烷氧基丙胺(Tomah PA1214,购自Tomah Products,Inc.)和216克(2.0摩尔)的70%乙醇酸(购自Aldrich ChemicalCo.)的水溶液在111克二甲苯中在惰性氮气气氛下于回流下(最高可达150℃)加热共4小时。用脱湿器通过共沸蒸馏恒定地除去乙醇酸溶液中的水和反应过程中形成的水。得到500克淡褐色液体,在二甲苯中的活性(active)约为80%。
实施例3
将246克(2.29摩尔)的乙醇酸(购自Aldrich Chemical Co.)的70%水溶液和402克(1.92摩尔)乙醚胺、C8-C10烷氧基丙胺(Tomah PA1214,购自Tomah Products,Inc.)和100克(0.37摩尔)动物脂胺(tallowamine)(Armeen HT,购自Akzo Chemicals,Inc.)在130克二甲苯中的混合物在惰性氮气气氛下于回流下(最高可达150℃)加热共7小时。用脱湿器通过与二甲苯的共沸蒸馏恒定地除去乙醇酸溶液中的水和反应过程中形成的水。得到724克淡褐白色固体,在二甲苯中的活性约为80%。
实施例4
将313克(1.5摩尔)乙醚胺、C8-C10烷氧基丙胺(Tomah PA1214,购自TomahProducts,Inc.)和159克(1.5摩尔)的85%DL-乳酸(购自Aldrich Chemical Co.)的水溶液在97克二甲苯中在惰性氮气气氛下于回流下(最高可达150℃)加热共4小时。用脱湿器通过共沸蒸馏恒定地除去乳酸溶液中的水和反应过程中形成的水。得到516克透明的褐色液体,在二甲苯中的活性约为80%。
实施例5
将419克(2.02摩尔)乙醚胺、C8-C10烷氧基丙胺(Tomah PA1214,购自TomahProducts,Inc.)和269克(1.97摩尔)的2,2-二羟甲基丙酸(购自Aldrich Chemical Co.,Inc.)在130克二甲苯溶剂中在惰性氮气气氛下于回流下加热共7小时。用脱湿器通过与二甲苯的共沸蒸馏恒定地除去反应过程中形成的水。得到650克浅黄色液体,在二甲苯中的活性约为80%。
实施例6
将137克(0.5摩尔)的脂族液态油胺(oleylamine)(Armeen OL,购自AkzoChemical,Inc.)和70%的乙醇酸(购自Aldrich Chemical Co.,Inc.)的溶液(54克,0.5摩尔,在反应的头2个小时内逐渐地加入)在150毫升二甲苯溶剂中在惰性氮气气氛下于回流下(最高可达150℃)加热共3小时。用脱湿器通过共沸蒸馏恒定地除去乙醇酸溶液中的水和反应过程中形成的水。然后将溶剂在最高可达160℃的温度下蒸馏汽提20分钟,接着在10-20mm/Hg的减压下于140℃蒸馏汽提45分钟。得到152克暗褐色固体。
用LVFA(低速摩擦仪器)试验和/或Buick 2.8L Fired Engine试验测量实施例中产物的减小摩擦性能。将添加剂以1.00或0.50或0.25%(重量)溶解在完全按配方制造的5W-30发动机矿物油中作为对比样品。
在LVFA试验中,在滑动速度(5-30ft/min)的范围内,于32、38、48和58psi下测量对比油和含有本发明产物的油的摩擦系数,在室温和250°F下均测量并进行平均。下表1中列出了试验油相对于对比油的摩擦系数的变化百分数。同时也列出了购得的摩擦改进剂,即单油酸甘油酯(GMO)的结果作为比较。摩擦系数的降低百分数越大,添加剂的有效性也就越高。实施例2的乙醚胺2-羟乙酰胺(etheramine glycolamide)在减小摩擦方面要比实施例6的油基2-羟乙酰胺(oleylglycolamide)添加剂和GMO要优越得多。表1摩擦系数的变化
   实施例     处理率%(重量)     摩擦系数的降低%
静摩擦系数 动摩擦系数
    1     0.5     26.9     18.5
    2     0.5     35.9     18.7
    6     0.5     23.1     12.0
    GMO     0.5     7.0     4.0
用3.8L Fired Engine试验测量每个样品的制动燃油消耗率(brake specific fuelconsumption,BSFC),将其结果与用作对比样品的未加入本发明产物的发动机油的结果进行比较。
试验一般是把添加剂掺加到在275°F的高温下运转的发动机的润滑油中。在某些情况下,225°F的较低温度被用来模拟典型的水冷却发动机的运转温度。
下表2中列出的燃料消耗的降低百分数的结果是相对于对比油所改进的百分数。BSFC的降低百分数越大,添加剂就越有效。这里同样也使用了GMO(单油酸甘油酯)的结果来对比。虽然减小摩擦的百分数良好,但是实施例1的通过椰子胺和乙醇酸缩合制得的添加剂不能以1.0%(重量)溶于试验油中。
                        表2燃料消耗的降低
实施例     处理率重量%     燃料消耗的降低%
    225°F     275°F
    1     1     -     9.9
    2     10.50.25     7.47.03.7     9.75.3-0.2*
    3     10.50.25     7.17.35.2     9.67.80.6
    5     10.50.25     6.96.23.5     7.70.0*-0.5*
    GMO     1    -----*     2.0
*没有响应
从低速摩擦仪器试验的结果和3.8L Fired Engine试验的结果可见,本发明产物显示了异常的减小摩擦性能,从而提高了其燃料经济并且其性能比购得的摩擦改进添加剂、单油酸甘油酯更好。在处理水平(treat level)低至1.00%(重量)时发现燃料消耗得益接近10%,这是从未有过的好。而且,在0.25%(重量)时就观察到了良好的燃料经济得益,显示了本发明一些产物的有效性高。
还用TGA(热解重量分析)来评定实施例产物在热分解过程中的清洁度,将其结果与购得的摩擦改进剂、单油酸甘油酯(GMO)(如下表3所示)进行比较。用热解重量分析仪在20℃/min下、以100ml/min的气流加热小样品来进行热解重量分析。记录425℃时剩下的残留物的百分数;几乎没有残留或没有残留是理想的。
                        表3清洁度
   实施例     热解重量分析在424℃时的残留%
    1     3.6
    2     3.5
    3     5.4
    4     1.0
    5     2.3
    6     13.1
    GMO     25.0
由表3中热解分析结果可见,本发明产物显示了比购得的摩擦改进剂、GMO异常高的清洁度。实施例2、3、4和5的乙醚胺2-羟乙酰胺比实施例6的油基2-羟乙酰胺和GMO在清洁度方面要好得多。
上表中LVFA和TGA的结果表明,在分解的清洁度方面,本发明产物作为减小摩擦剂也要比单油酸甘油酯好得多。据信,酰胺上的附加基团(如羟基、氢基、亚氨基和烷氧基)与酰胺协同作用能得到更好的表面活性。
实施例7
使用实施例2的反应产物,制得如下燃料添加剂提浓物制剂。制剂                               A     B     C     D     E     F组分(重量%范围)实施例2的反应产物                15.0  14.88  22.7  19.46  29.7  10.0洗涤剂曼尼期碱缩合产物(Ethyl 4961M)          30.12  47.3         40.3  45.0聚异丁烯胺(Pluradyne AP-92M)     30.0               40.54溶剂异丙醇                           18.33 18.33  10.0  13.33  10.0  8.0二甲苯                           36.67 36.67  20.0  26.67  20.0  37.0实施例8使用实施例4的反应产物,制得如下燃料添加剂提浓物制剂。制剂                              A      B     C      D      E     F组分(重量%范围)实施例4的反应产物                15.0  14.88  22.7  19.46  29.7  10.0洗涤剂曼尼期碱缩合产物(Ethyl 4961M)          30.12  47.3         40.3  45.0聚异丁烯胺(Pluradyne AP-92M)     30.0               40.54溶剂异丙醇                           18.33 18.33  10.0  13.33  10.0  8.0二甲苯                           36.67 36.67  20.0  26.67  20.0  37.0
现已完整地说明了本发明,应该理解,在不偏离本发明的精神和主要特征的情况下,本发明可以有其它的具体形式和变化。因此,上述实施方案在所有方面都只能被认为是说明而不是限制,本发明的范围是所附权利要求书所指出的,而不是上述说明书所叙述的。在与本发明权利要求书等价的意义和范围内的所有变化都被认为是包括在本发明内。

Claims (16)

1.一种润滑剂组合物,它包含润滑油或由其制得的润滑脂,以及减小摩擦量的非硼酸化的反应产物,该反应产物是通过R1(OR2)aNH2和羟基羧酸反应制得的,其中R1是烃基或C1-C60烷基,R2是C1-C4亚烷基,a是1至12。
2.如权利要求1所述的润滑剂组合物,它还包含分散剂。
3.如权利要求1所述的润滑剂组合物,其中所述润滑油选自矿物油、合成油,或者它们的混合物。
4.如权利要求1所述的润滑剂组合物,其中所述伯醚胺包含C6-C12烷氧基丙胺的混合物。
5.如权利要求1所述的润滑剂组合物,其中所述羟基羧酸是α-羟基羧酸。
6.如权利要求5所述的润滑剂组合物,其中所述α-羟基羧酸是乙醇酸。
7.如权利要求1所述的润滑剂组合物,其中所述反应还包含烷基胺。
8.如权利要求7所述的润滑剂组合物,其中所述烷基胺是动物脂胺。
9.如权利要求1所述的润滑剂组合物,其中反应产物的存在量在0.1-10.0%(重量)的范围内。
10.一种润滑添加剂提浓物,它包含减小摩擦量的非硼酸化的如下化学式的反应产物
R1(OR2)aNHCOR3OH其中R1是烃基或C1-C60烷基;R2是C1-C4亚烷基;R3是C1-C4亚烷基或被取代的亚烷基、芳基、烷芳基或环烷基;a是1至12;以及至少一种分散剂。
11.一种燃料组合物,它包含内燃机燃料和减小摩擦量的非硼酸化的产物,该产物是通过R1(OR2)aNH2和羟基羧酸反应制得的,其中R1是C1-C60烷基,R2是C1-C4亚烷基,a是1至12。
12.如权利要求11所述的燃料组合物,其中R1是C8至C10烷基,R2是C3亚烷基,a是1,所述羟基羧酸是乙醇酸。
13.如权利要求11所述的燃料组合物,它还包括选自聚亚烷基胺和曼尼期碱缩合产物的洗涤剂。
14.如权利要求11所述的燃料组合物,其中内燃机燃料选自馏出燃料、汽油、烃、醇、氧化烃,以及它们的混合物。
15.一种燃料添加剂提浓物,它包含减小摩擦量的非硼酸化的如下化学式的反应产物
R1(OR2)aNHCOR3OH其中R1是烃基或C1-C60烷基;R2是C1-C4亚烷基;R3是C1-C4亚烷基或被取代的亚烷基、芳基、烷芳基或环烷基;a是1至12;以及至少一种洗涤剂。
16.一种用于减小和/或防止内燃机运转中摩擦的方法,它包括向所述发动机中加入液态燃料组合物,该组合物包含每1000桶燃料25至250磅的非硼酸化的产物,该产物是通过R1(OR2)aNH2和羟基羧酸反应得到的,其中R1是烃基或C1-C60烷基,R2是C1-C4亚烷基,a是1至12。
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1295307C (zh) * 2003-04-22 2007-01-17 乙基公司 作为燃料组合物添加剂的磨擦改良剂羧酸烷氧基胺盐及其使用方法
CN101313011B (zh) * 2005-09-22 2011-03-30 东丽株式会社 聚芳撑硫醚及其制备方法
CN104293418A (zh) * 2013-07-18 2015-01-21 雅富顿化学公司 用于润滑油的酰胺醇摩擦改性剂
CN106398808A (zh) * 2015-03-23 2017-02-15 科聚亚公司 包含烷氧基化的胺的低灰分润滑剂和燃料添加剂
CN107406800A (zh) * 2015-03-09 2017-11-28 Jxtg能源株式会社 润滑脂组合物

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10036956A1 (de) * 2000-07-28 2002-02-07 Basf Ag Amide von Hydrocarbylaminen und Verwendung dieser Amide
US6358896B1 (en) * 2000-12-06 2002-03-19 Infineum International Ltd. Friction modifiers for engine oil composition
DE10109845A1 (de) * 2001-03-01 2002-09-05 Basf Ag Emulgatoren, insbesondere auf Basis von Polyisobutylenaminen
DE10125158A1 (de) * 2001-05-22 2002-12-05 Basf Ag Nieder-und hochmolekulare Emulgatoren, insbesondere auf Bassis von Polyisobutylen, sowie deren Mischungen
US7204863B2 (en) 2001-12-11 2007-04-17 Exxonmobil Research And Engineering Company Gasoline additives for reducing the amount of internal combustion engine intake valve deposits and combustion chamber deposits
US7226489B2 (en) 2001-12-12 2007-06-05 Exxonmobil Research And Engineering Company Gasoline additives for reducing the amount of internal combustion engine intake valve deposits and combustion chamber deposits
US7846224B2 (en) * 2002-04-24 2010-12-07 Afton Chemical Intangibles, Llc Methods to improve the low temperature compatibility of amide friction modifiers in fuels and amide friction modifiers
US6866690B2 (en) * 2002-04-24 2005-03-15 Ethyl Corporation Friction modifier additives for fuel compositions and methods of use thereof
US7402185B2 (en) * 2002-04-24 2008-07-22 Afton Chemical Intangibles, Llc Additives for fuel compositions to reduce formation of combustion chamber deposits
DE102004038113A1 (de) 2004-08-05 2006-03-16 Basf Ag Stickstoffhaltige heterocyclische Verbindungen als Reibverschleißvermindernder Zusatz zu Kraftstoffen
US20060196111A1 (en) * 2005-03-04 2006-09-07 Colucci William J Fuel additive composition
BRPI0711265A2 (pt) * 2006-05-03 2011-08-30 Shell Int Research composição de óleo lubrificante, método de redução de depósito em um motor de combustão interna, e, uso de uma composução de óleo lubrificante
JP2013500237A (ja) * 2008-07-31 2013-01-07 シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ ポリ(ヒドロキシカルボン酸)アミド塩誘導体及びそれを含有する潤滑組成物
BRPI0916886A2 (pt) * 2008-07-31 2016-02-10 Shell Int Research composições de combustível líquido, e lubrificante, e, método para operar um motor de combustão interna.
US20100132253A1 (en) * 2008-12-03 2010-06-03 Taconic Energy, Inc. Fuel additives and fuel compositions and methods for making and using the same
GB0909351D0 (en) * 2009-06-01 2009-07-15 Innospec Ltd Improvements in efficiency
US8557002B2 (en) 2010-11-12 2013-10-15 Baker Hughes Incorporated Fuel additives for enhanced lubricity and anti-corrosion properties
US9909081B2 (en) * 2014-10-31 2018-03-06 Basf Se Alkoxylated amides, esters, and anti-wear agents in lubricant compositions
US9353326B1 (en) * 2016-01-28 2016-05-31 Afton Chemical Corporation Synergistic fuel additives and fuels containing the additives
WO2017144378A1 (de) 2016-02-23 2017-08-31 Basf Se HYDROPHOBE POLYCARBONSÄUREN ALS REIBVERSCHLEIß-VERMINDERNDER ZUSATZ ZU KRAFTSTOFFEN

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4280916A (en) * 1980-03-31 1981-07-28 Shell Oil Company Lubricant composition
US4406803A (en) * 1980-11-24 1983-09-27 Chevron Research Company Method for improving fuel economy of internal combustion engines
US4867752A (en) * 1982-11-30 1989-09-19 Mobil Oil Corporation N-alkyl amides as friction-reducers for lubricants and fuels
US4617026A (en) * 1983-03-28 1986-10-14 Exxon Research And Engineering Company Method for improving the fuel economy of an internal combustion engine using fuel having hydroxyl-containing ester additive
US4512903A (en) * 1983-06-23 1985-04-23 Texaco Inc. Lubricant compositions containing amides of hydroxy-substituted aliphatic acids and fatty amines
US4789493A (en) * 1986-02-05 1988-12-06 Mobil Oil Co Lubricants containing n-alkylalkylenediamine amides
US4741848A (en) * 1986-03-13 1988-05-03 The Lubrizol Corporation Boron-containing compositions, and lubricants and fuels containing same
US4808196A (en) * 1987-04-02 1989-02-28 Mobil Oil Corporation Fuels containing N-alkylalkylenediamine amides
DE3826608A1 (de) * 1988-08-05 1990-02-08 Basf Ag Polyetheramine oder polyetheraminderivate enthaltende kraftstoffe fuer ottomotoren
DE3838918A1 (de) * 1988-11-17 1990-05-23 Basf Ag Kraftstoffe fuer verbrennungsmaschinen
DE3942860A1 (de) * 1989-12-23 1991-06-27 Basf Ag Kraftstoffe fuer ottomotoren
FR2681312A1 (fr) * 1991-09-16 1993-03-19 Francais Prod Ind Cfpi Solution lubrifiante et desinfectante pour chaine transporteuse de recipients dans l'industrie agro-alimentaire et procede pour sa mise en óoeuvre.
US5169410A (en) * 1991-09-24 1992-12-08 Betz Laboratories, Inc. Methods for stabilizing gasoline mixtures
US5637121A (en) * 1994-12-30 1997-06-10 Chevron Chemical Company Poly(oxyalkylene) aromatic amides and fuel compositions containing the same

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1295307C (zh) * 2003-04-22 2007-01-17 乙基公司 作为燃料组合物添加剂的磨擦改良剂羧酸烷氧基胺盐及其使用方法
CN101313011B (zh) * 2005-09-22 2011-03-30 东丽株式会社 聚芳撑硫醚及其制备方法
CN104293418A (zh) * 2013-07-18 2015-01-21 雅富顿化学公司 用于润滑油的酰胺醇摩擦改性剂
CN107406800A (zh) * 2015-03-09 2017-11-28 Jxtg能源株式会社 润滑脂组合物
CN107406800B (zh) * 2015-03-09 2021-06-01 Jxtg能源株式会社 润滑脂组合物
CN106398808A (zh) * 2015-03-23 2017-02-15 科聚亚公司 包含烷氧基化的胺的低灰分润滑剂和燃料添加剂
CN106398808B (zh) * 2015-03-23 2021-03-30 科聚亚公司 包含烷氧基化的胺的低灰分润滑剂和燃料添加剂

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EP0897419A4 (en) 2001-01-17
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NZ332593A (en) 2000-03-27
CN1095872C (zh) 2002-12-11
US5858029A (en) 1999-01-12
CA2253334A1 (en) 1998-07-16
AU5734398A (en) 1998-08-03
AU716468B2 (en) 2000-02-24
EP0897419A1 (en) 1999-02-24

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