CN1230211A - 能生成氢过氧自由基的抗氧化剂和抗氧化剂助促进剂 - Google Patents
能生成氢过氧自由基的抗氧化剂和抗氧化剂助促进剂 Download PDFInfo
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- CN1230211A CN1230211A CN97197896A CN97197896A CN1230211A CN 1230211 A CN1230211 A CN 1230211A CN 97197896 A CN97197896 A CN 97197896A CN 97197896 A CN97197896 A CN 97197896A CN 1230211 A CN1230211 A CN 1230211A
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Images
Classifications
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- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
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- C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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- C10M169/04—Mixtures of base-materials and additives
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Abstract
一种含有连接在有机主链上的伯脂族羟基的抗氧化剂,从而在氧化中就地产生能促进自由基清除剂和氢过氧化物分解剂型抗氧化剂的效能的氢过氧化部分。该抗氧化剂优选是(a)有约l-35%未转化的羟基的高羟基多羟基酯;(b)多元醇和至少一种选自酚酸、芳族氨基酸、磷酸和硫酸的酸的反应产物;(c)(b)的反应产物,其中未转化的羟基与一种易离去基团反应,从而在水解或氧化时生成自由的-CH2OH基;和(d)(a)、(b)或(c)的抗氧化剂与至少一种选自矿物油、多羟基酯、聚α-烯烃、燃料、低聚物和高聚物的材料混合或接枝到该材料上。
Description
本发明涉及效果提高的抗氧化剂和抗氧化剂助促进剂。该独特的抗氧化剂优选这样形成,即,使它们含有预定量的未转化的羟基,这些羟基氧化生成氢过氧自由基或部分(HOO·)。该氢过氧自由基与烷基过氧自由基(RO·)或烷基氢过氧自由基(ROO·)反应生成稳定的中间体和分子氧。可使用本发明抗氧化剂本身、将其接枝到常规的抗氧化剂上作为抗氧化剂助促进剂,或接枝到其它材料上,诸如矿物油、多羟基酯、聚α-烯烃基料、燃料、低聚物和高聚物、从而提供抗氧化剂保护。
发明背景
现在商品用途的润滑剂是由各种天然和合成的基料与各种添加组份和溶剂根据它们预定的用途混合制备的。基料一般包括矿物油、高精炼矿物油、聚α-烯烃(PAO)、聚(亚烷基)二醇(PAG)、磷酸酯、硅油、双酯类和多羟基酯。
当热和氧化稳定性很苛刻时,通常用多羟基酯作为在润滑剂应用中的基料。尽管与其它基料(例如矿物油、聚α-烯烃等)相比它们具有热/氧化稳定性,但甚至这些合成的酯润滑剂发生氧化降解而不经进一步改性在氧化条件下不能长期使用。已知这种降解与酯基料的氧化和水解相关。
常用的合成多羟基酯润滑油配方需要加入抗氧化剂(也称为氧化抑制剂)。抗氧化剂降低酯基料在使用中变质的趋势,变质可通过氧化产物证实,诸如在金属表面上的淤渣和清漆状沉积物,还可通过粘度和酸度的增加证实。这类抗氧化剂包括芳胺(例如,二辛基二苯基胺(V-81)和苯基-α-萘胺)等。
经常更换润滑油或在其中加入抗氧化剂来消除氧化提高了维护发动机或机器的总费用。最理想的是提高常规抗氧化剂的效果(即提高在配制好的产品中抗氧化剂的效能)或制备一种酯基料,与常规的合成酯基料相比,其主要表现出提高的热/氧化稳定性,并且其中酯基料不因分解(即,氧化降解)需要经常更换。消除或降低通常加入这类润滑剂基料中的抗氧化剂的量从经济上也是理想的。
受到热氧化应力,一个弱碳氢键被断开,生成在酯上的一个不稳定的碳自由基。常规抗氧化剂的作用是将一个氢原子传递给该不稳定的碳自由基并完成自由基的“恢复”。下面的方程式描述了抗氧化剂(AH)的作用:
抗氧化剂分子被转化为一个自由基,但这个自由基(A·)比酯基体系的自由基要稳定得多。这样,酯的有效寿命被延长了。当加入的抗氧化剂耗尽时,酯自由基就不能恢复,于是多羟基酯成份发生氧化降解。本领域公知的一种相对热/氧化稳定性的表征是用高压差示扫描量热法(HPDSC)。
HPDSC已被用于评价配制的汽车润滑油的热/氧化稳定性(见J.A.Walker,W.Tsang,SAE 801383)、用于评价合成的润滑油(见M.Wakakura,T.Sato,日本石油学会期刊<Journal of Japanese PetroleumInstitute>,24(6),PP.383-392(1981))和评价由润滑油衍生的多羟基酯(见A.Zeeman,热化学(Thermochim),Acta,80(1984)1)。在这些评价中,测定的散装油氧化的时间是诱导时间。已表明较长的诱导时间对应于有较高抗氧化剂浓度的油或对应于有更有效抗氧化剂的油或对应于给定的抗氧化剂的固定的水平,也已表明较长的诱导时间对应于有本质上更稳定的基料的油。对于汽车润滑油,较高的诱导时间与粘度转折点时间相关。
在此所述的HPDSC的应用提供了一种贯穿氧化诱导时间的测定稳定性的方法。多羟基酯可与恒定量的抗氧化剂二辛基二苯基胺混合。该固定量的抗氧化剂为多羟基酯基料抵抗整体氧化提供了恒定水平的保护。这样,用这种方法测定的具有较长诱导时间的油有对氧化更强的本质上的抵抗力。对于本发明不加抗氧化剂的高羟基酯,较长的诱导时间反映了这种基料本身的较强的稳定性以及由于自由羟基导致的这种酯的天然抗氧化性。
本发明人发现了一种独特的多羟基酯组合物,与常规的合成的多羟基酯组分相比,其具有提高的热/氧化稳定性。这是通过由多元醇和支化的和/或线性的羧酸或芳族酸用使其具有相当量未转化的羟基的方法合成多羟基组分来实现的。具有高度支化的多羟基酯主链使高羟基酯的作用与抗氧化剂类似,即,使该新的多羟基酯组合物的热/氧化稳定性大大提高,正如高压差示扫描量热法(HPDSC)所测定的那样。这种新的多羟基酯组分提供了一种分子内机理,其能清除烷氧化物和烷基过氧化物自由基,从而根本上降低了氧化降解可发生的速率。
设计到本发明的新多羟基酯组合物中的热稳定性和氧化稳定性消除或降低了必须加入到特别的润滑油中的抗氧化剂的水平,从而在根本上节约了制造润滑油的费用。另外,当本发明的新的高羟基多羟基酯接枝到包括润滑油、燃料、低聚物和高聚物的其它配制的产品时,能降低所需的其它抗氧化剂的水平,这样可能降低配制的费用而达到理想的性能目标。
常规配方的另一个问题是在各自基料中溶解常规抗氧化剂的能力变化很大,在一些例子中,由于溶解度有限而不能使用选定的抗氧化剂。本发明还提供了一种将添加剂混入配方中的方法,这些配方通过常规的烃键与正在讨论的添加剂连接可能是溶解性很差的。高羟基酯因此不但提供了可溶性,而且还提供了正在讨论的添加剂的抗氧化性。
本发明的高羟基多羟基酯接枝到低聚物、高聚物等上时,能产生改进的氧化稳定性,而不受已知常规的会产生发色体的抗氧化剂才有的潜在影响,对选择的聚合物应用有显著影响。
本发明还提供了许多其它优点,这通过下列描述会被证实。
本发明概述
本发明的抗氧化剂优选是一种独特的多羟基酯,其具有未转化的羟基,由多元醇与支化的和/或线性的羧酸或芳族酸反应生成,从而使未转化的羟基氧化形成过氢氧部分(HOO·)。这类抗氧化剂含有与有机主链连接的伯脂族羟基,从而在氧化中就地生成能促进自由基清除剂效果的氢过氧部分和氢过氧化物分解剂型抗氧化剂。
本发明覆盖的抗氧化剂包括一般类型的多羟基酯、酚类、芳族胺、亚磷酸酯、含硫的抗氧化剂以及任何作为自由基抑制剂或氢过氧化物分解剂的常规抗氧化剂;条件是这些抗氧化剂含有一个未转化的羟基,其能形成一个氢过氧自由基或部分(HOO·)。基于使用的酸,生成的酯产物是抗氧化剂或是抗氧化剂助促进剂。
抗氧化剂包含以下的反应产物:支化的或线性通式为R(OH)n的醇,其中R是脂族或环脂族的有约2-20个碳原子的基团和n至少为2;和至少一种碳原子数在约C2-C20之间的支化的或线性的羧酸;其中所述的抗氧化剂的羟基数在约5-180之间。这类抗氧化剂的未转化的羟基优选与一个易离去基团反应,从而在被化学保护的衍生物水解或氧化时产生自由的-CH2OH基团。
供选择地,本发明的抗氧化剂包括经接枝反应对一般抗氧化剂(AH)的改性,生成新的抗氧化剂,其在水解和/或氧化中生成自由的-CH2OH基团。这种抗氧化剂通过用包含未转变的-CH2OH基部分的反应产物接枝一般的抗氧化剂(AH)形成。优选的反应产物包括YH与多羟基二丙烯酸酯的反应产物,其中Y选自RS、R2H、(RO)2PHO、酚类和它们的混合物;条件是RS是含硫抗氧化剂的一部分,R2N芳族胺或烷基胺抗氧化剂和(RO)2PHO是亚磷酸酯抗氧化剂。
供选择地,本发明的抗氧化剂还包括那些不含游离羟基,也不含水解时会产生-CH2OH基部分而氧化时产生羟基的化学键的抗氧化剂。这种抗氧化剂还应具有促进的抗氧化剂能力,这是因为后继的-CH2OH的氧化反应生成了氢过氧部分(HOO·)。氢过氧自由基或部分随后可以与烷基过氧自由基或烷基氢过氧自由基反应生成稳定的中间体(例如ROOH)和分子氧。这类抗氧化剂可由反应产物:(1)三(羟甲基)氨基甲烷和甲醛衍生,生成1-氮杂-3,7-二氧杂-双环[3.3.0]辛基-5-甲醇;(2)三(羟甲基)氨基甲烷和环己酮衍生,生成2,2-五亚甲基-1,3-噁唑烷-4,4-二甲醇;(3)三(羟甲基)氨基甲烷和线性的或支化的羧酸衍生,生成具有通式
R(C=O)NHC(CH2OH)3的酰胺,其中R是由线性或支化的酸与三(羟甲基)氨基甲烷的反应产物衍生的线性或支化的烷基链;和(4)三(羟甲基)氨基甲烷和线性或支化的羧酸衍生,生成具有通式的取代的噁唑烷,其中R是由所述线性或支化的羧酸衍生的线性或支化的烷基。
本发明的独特的高羟基多羟基酯抗氧化剂接枝到矿物油、多羟基酯、聚α-烯烃基料、燃料、低聚物和高聚物上时也提高了那些材料的氧化稳定性。
本发明还包括一种润滑剂,其由至少一种上文提出的具有未转化羟基的合成的多羟基酯组分和一种润滑剂添加成分制备。另外,在润滑剂中还可加入一种溶剂,其中润滑剂含有约60-99%重量的合成的多羟基酯成分,约1-20%重量的添加组分和约0-20%重量的稀释剂。
润滑剂优选选自下列之一:曲轴箱机器润滑油、双冲程引擎油、弹射器油、液压油、钻探油、透平油、润滑脂、压缩机油、齿轮油和功能流体。
添加组分含有至少一种选自下列的添加剂:粘度指数改进剂、缓蚀剂、氧化抑制剂、分散剂、润滑油流动改进剂、去垢剂和防锈剂、倾点下降剂、抗泡沫剂、抗磨损剂、密封膨胀剂、摩擦改性剂、耐特压剂、颜色稳定剂、破乳剂、湿润剂、水损失改进剂、杀菌剂、钻头润滑剂、增稠剂或胶凝剂,抗乳化剂、金属钝化剂和增溶剂。
还可根据本发明形成其它润滑剂,通过将本发明的这种独特的合成的高羟基多羟基酯组分与至少一种另外的选自下列的基料混合,这些基料包括:矿物油、高精馏矿物油、聚α-烯烃、聚(亚烷基)二醇、磷酸酯、硅油、双酯和多羟基酯。该合成的多羟基酯组分以约1-50%重量的量、优选1-25%重量、最优选1-15%重量的量与另外的基料混合,重量百分比基于混合的基料的总量计。
附图说明
附图1是HPDSC结果对具有键连的未转化的羟基的各种多羟基酯的羟基数的图;和
附图2是HPDSC结果对各种与聚α-烯烃(PAO)混合的酯的百分数的图。
优选实施方案的详述
高羟基值的酯(即,羟基值在约大于5到180之间、优选大于5到70、最优选约10-50,由选择的羧酸--诸如3,5,5-三甲基己酸或2-乙基己酸和它们的联合--衍生,具有诸如烷基过氧自由基和烷基氢过氧自由基的清除自由基的能力。这样,当高羟基酯处于氧化条件时,用此后所示的HPDSC研究,它们趋于耐氧化,因为它们具有本质的抗氧化性。
另外,相同的酯能通过提供抗氧化保护能为其它诸如矿物油,多羟基酯、聚α-烯烃基料、燃料、低聚物和高聚物的材料提供氧化稳定性。这类高羟基多羟基酯的优点是它们作为抗氧化剂使用可降低对其它诸如酚类或芳香胺的抗氧化剂的依赖。
当这些高羟基多羟基酯作为稀释溶剂使用时,还可以提高诸如酚类或二苯基胺的常规抗氧化剂的性能。该高羟基酯对自由基的清除协同了常规抗氧化剂对自由基的清除,从而促进了它们的性能。另外,由于高羟基酯的极性,其能提高用于润滑剂和燃料配制的添加剂的溶解性。高羟基酯与其它添加剂--其中一些本身可以是抗氧化剂-的反应可提高这些添加体系的油溶解性并且同时为配方提供促进的抗氧化性。
本发明的高羟基酯作为抗氧化剂的应用与下述机理符合。氧化的产物用于构建下述降解路径,其描述了氧化期间高羟基酯如何降解。高羟基酯作为抗氧化剂的性能取决于高羟基酯本身的氧化降解。本质的抗氧化性的关键是形成氢过氧部分(HOO·)。如下所示,氢过氧自由基与其它形成的反应产物的反应导致了氧化反应的抑制。氧化的抑制妨碍了链增长步骤,通常反映着快速增长还是氧化降解。
下列反应表明了关于高羟基多羟基酯的本质抗氧化性的抑制反应:
下列反应表明不存在抗氧化剂的典型的增长反应:
高羟基酯的影响是降低其本身和与其混合的烃或经永久化学键已与其连接的烃的氧化倾向。因此,高羟基酯的性能可以影响其它添加剂、基料和诸如聚合物的较高分子量的低聚物的氧化。
根据本发明的另一个优选的实施方案涉及通过将其接枝到多羟基化合物--诸如单季戊四醇、二-季戊四醇、工业级季戊四醇、三羟甲基丙烷、三羟甲基乙烷、新戊二醇或任何其它烃一上,从而或作为接枝反应的结果或作为水解或其它化学反应的结果生成-CH2OH基,提高了抗氧化剂清除自由基的能力。这个实施方案的要求是当可能时化合物的烃部分含有在此特指的,选定的支化链。
根据这个实施方案,假定抗氧化剂是自由基清除剂并表示为AH,其中H假定是在自由基清除反应中的活性氢原子:
提高了效能的抗氧化剂的一个例子是1摩尔季戊四醇和2-3摩尔4-(对-2,6-二叔丁基苯酚)丁酸的反应产物。2,6-二叔丁基苯酚的抗氧化剂功能是公知的。1-2摩尔当量的自由羟基的存在通过释放2摩尔当量的氢过氧部分提高抗氧化性。氢过氧部分与自由的烷基氢过氧自由基或烷基过氧自由基的反应导致了更稳定的烷基氢过氧化物或醇和分子氧的生成。
上述机理表明了自由羟基部分的氧化降解如何导致清除烷基过氧自由基和烷基氢过氧自由基的活性中间体(即HOO·)的生成。清除反应的产物是更稳定的中间体和分子氧。这种化学成功的关键是化合物其余的部分在氧化环境中是相对非活性的。使用诸如酚类和芳族胺的芳族抗氧化剂制备一种抗氧化剂配合物,其在氧化环境中除了与AH相关的自由基清除反应或-CH2OH生成HOO·的反应之外是相对非活性的。这个实施方案覆盖的抗氧化剂包括一般的酚类、芳族胺、亚磷酸酯和含硫的抗氧化剂以及任何作为自由基抑制剂或氢过氧化物分解剂的常规抗氧化剂。
根据本发明的另一实施方案涉及通过接枝反应改进的一般抗氧化剂(AH)、接枝反应生成新的抗氧化剂,其在水解和/或氧化中产生自由的-CH2OH基团。这类抗氧化剂的一个例子与上述酚类抗氧化剂相同,其中自由的羟基已与一个易离去基团反应。离去基团在水解条件下应能容易地生成自由的-CH2OH部分,后者继而氧化生成HOO·部分。这种接枝反应产生新的抗氧化剂,其由包括YH和一种多羟基二丙烯酸酯的反应的反应产物组成,其中Y选自RS、R2N、(RO)2PHO、酚类和它们的混合物;条件是RS为含硫抗氧化剂的部分,R2N是芳族胺或烷基胺抗氧化剂,(RO)2PHO是亚磷酸酯抗氧化剂。其它抗氧化剂包括酚类或任何上述包括诸如ZDDP的含金属抗氧化剂的抗氧化剂的联合。
供选择地,可以制备抗氧化剂体系使其不具有自由羟基或任何在水解时产生-CH2OH部分在后继的-CH2OH部分的氧化反应中生成HOO·的化学键。本发明的不含自由羟基或任何在水解时产生-CH2OH部分但在氧化时产生羟基的化学键的抗氧化剂可由下列反应产物衍生:
(1)三(羟甲基)氨基甲烷和甲醛,生成1-氮杂-3,7-二氧杂-双环[3.3.0]辛基-5-甲醇;
(2)三(羟甲基)氨基甲烷和环己酮,生成2,2-五亚甲基-1,3-噁唑烷-4,4-二甲醇;
(3)三(羟甲基)氨基甲烷和线性的或支化的羧酸,生成具有通式
R(C=O)NHC(CH2OH)3的酰胺,其中R是由线性或支化的酸与三(羟甲基)氨基甲烷的反应产物衍生的线性的或支化的烷基链;和
优选通过多羟基化合物与至少一种酸(例如支化的和/或线性的单羧酸、二酸或芳族酸)反应形成本发明的多羟基酯组分。在多羟基酯组分中,多羟基酯优选比所用酸的量过量约10-35当量百分比或更多。调整自由的多元醇的组分从而得到产物酯的理想组分。
根据本发明形成的高羟基酯在用或不用常规抗氧化剂--诸如V-81下一般耐高温氧化。
酸优选为高度支化的和/或线性的单羧酸,这样键连在生成的酯组分上的未转化的羟基,作用与抗氧化剂类似,从而其向在酯分子处于热应力下的时候生成的不稳定的碳自由基转移一个氢原子,这样进行自由基的“复原”(即,将碳自由基转化为稳定的醇和氧)。这些作为内抗氧化剂的未转化的羟基可基本上减少或在某些情况下消除在多羟基酯组分中加入昂贵的抗氧化剂的需要。另外,具有键连其上的未转化羟基的酯基本上表现出比具有相同量混合的抗氧化剂的酯提高了的热/氧化稳定性。
优选进行酯化时有或没有催化剂,温度在约140-250℃之间的范围内,压力在约30mmHg-760mmHg(3.999-101.308kPa)之间的范围内,反应进行约0.1-12小时,优选1-8小时。反应器中的化学计量是可变的,因为能够真空汽提过量的酸而生成优选的最终组分。
如果在催化条件下进行酯化,那么优选的酯化催化剂是钛、锆和锡催化剂,诸如钛、锆和锡的醇盐、羧酸盐和螯合物。选定的酸催化剂也可用于该酯化过程。见US-A-5324853(Jones等人),1994年6月28日公开,US-A-3056818(Werber),1962年10月2日公开,这两篇引用在此作为参考。
醇类
可与支化的酸或支化的和线性的酸的混合物反应的醇的例子是多元醇(即,多羟基化合物),由通式:
R(OH)n表示,其中R是任何脂族或环脂族烃基(优选烷基)和n至少为2。烃基可以含有约2-20个或更多的碳原子,烃基还可以含有取代基,诸如氯、氮和/或氧原子。多羟基化合物一般可含有一个或多个氧亚烷基,这样,多羟基化合物包括诸如聚醚多元醇的化合物。在用于形成羧酸酯的多羟基化合物中,碳原子数(即,碳数,其中作为在本申请全文中使用的术语碳数根据具体情况是指酸或醇中碳原子的总数)和羟基数(即,羟基的数量)可以在很宽的范围内变化。
下列醇特别用作多元醇:新戊二醇2,2-二羟甲基丁烷、三羟甲基乙烷、三羟甲基丙烷、三羟甲基丁烷、单季戊四醇、工业级季戊四醇、二-季戊四醇、三-季戊四醇、己二醇、丙二醇和聚(亚烷基)二醇(例如,聚乙二醇、聚丙二醇、聚丁二醇等以及它们的混合物,诸如乙二醇和丙二醇的聚合的混合物)。最优选的醇是工业级(例如接近88%单季戊四醇、10%二-季戊四醇和1-2%三-季戊四醇)季戊四醇、单季戊四醇、二-季戊四醇、新戊二醇和三羟甲基丙烷。
支化的酸
优选支化的酸是单羧酸,其碳数在约C5-C13之间的范围内,更优选约C7-C10,其中甲基或乙基支链是优选的。优选至少一种单羧酸选自:2,2-二甲基丙酸(新戊酸)、新庚酸、新辛酸、新壬酸、异己酸、新癸酸;2-乙基己酸(2EH)、3,5,5-三甲基己酸(TMH)、异庚酸、异辛酸、异壬酸和异癸酸。一种特别优选的支化的酸是3,5,5-三甲基己酸。在此使用的术语“新”指三烷基乙酸,即在α碳上被烷基三取代的酸。如下所示定义的通式结构,这些烷基等于或大于CH3:其中R1、R2和R3大于或等于CH3并且不等于氢。
线性酸
优选的单和/或二线性羧酸是碳数在约C2-C20、优选C2-C10之间范围内的任何线性饱和的烷基羧酸。
一些线性羧酸的例子包括乙酸、正丙酸、正戊酸、正庚酸、正辛酸、正壬酸和正癸酸。选定的多元酸包括任何C2-C12多元酸,例如己二酸、壬二酸、癸二酸和十二烷二酸。
芳族酸
根据本发明使用的芳族酸包括任何芳族抗氧化剂的酸,诸如酚类和芳胺的酸。特别有利的是3-(对-2,6-二叔丁基苯酚)丁酸。
抗氧化剂
可通过将抗氧化剂接枝到多元醇或任何烃上使-CH2OH基要么作为接枝反应的结果要么作为水解或其它化学反应的结果生成,从而提高这些抗氧化剂的清除自由基的能力。适合接枝的抗氧化剂包括但不限于一般的酚类、芳胺、亚磷酸酯、含硫抗氧化剂和任何作为自由基抑制剂或氢过氧化物分解剂的抗氧化剂。
抗氧化剂助促进剂
上述高羟基多羟基酯可接枝到任何其它材料上为之提供氧化稳定性。这些其它材料可包括矿物油、多羟基酯基料、聚α-烯烃基料、燃料、低聚物和高聚物。
根据本发明具有明显未转化羟基的多羟基酯成分的合成过程一般按照下列方程: (方程1)其中n是至少为2的整数,R是含有约2-20或更多碳原子和任意的诸如氯、氮和/或氧原子取代基的任何脂族或环脂族烃基,R′是有约C4-C12、更优选约C6-C9个碳原子的任何支化的脂族烃基,其中优选甲基或乙基支链,(i)是约0-n的整数。
可使用上述方程1的反应产物本身作为润滑剂基料或与其它基料--诸如矿物油、高精馏的矿物油、聚α-烯烃(PAO)、聚(亚烷基)二醇(PAG)、磷酸酯、硅油、二酯和多羟基酯--的混合物。当与其它基料混合时,基于混合的基料的总量,根据本发明的部分酯成分优选以约1-50%(重量)、更优选约1-25%(重量)、最优选约1-15%(重量)的量存在。
本发明还包括有提高了的热/氧化稳定性的高羟基复合酯。经多元醇、单羧酸和多元酸(诸如己二酸)的反应制备复合酸酯。与一般的多羟基酯(即,多元醇和单羧酸)相比,由于生成了二聚物、三聚物和其它低聚物,复合酸酯具有较高的粘度。正如多羟基酯的情况一样,一般用生成高转化的多羟基部分的方法制备复合酸酯。这种转化的测定由羟基数表示。例如,用于航空透平油的多羟基酯一般具有类似于5mg KOH/g量级或更少的羟基数,显示非常高的转化。本发明人现已发现不完全或部分转化复合酸酯实际上可生成一种用HPDSC测定比低羟基数复合酸酯热/氧化稳定性更好的产物。
由多元醇、C6-C13醇和单羧酸或多元酸反应制备复合醇酯。与一般多羟基酯(即多元醇和单羧酸)相比,复合醇酯、类似的复合酸酯具有较高的粘度。本发明人已发现不完全或部分转化复合醇酯实际上可生成一种由HPDSC测定比低羟基数复合酸酯热/氧化稳定性更好的产物。
本发明还包括由线性或支化的酸和诸如钛、硅、铝、镍、铁、铜等的一种金属衍生的金属羧酸配合物,其表现出提高的热/氧化稳定性。
根据本发明的多羟基酯可用于各种润滑剂配方,诸如曲轴箱机器润滑油(即旅行车发动机油,重型柴油发动机油、旅行车柴油)、双冲程引擎油、弹射器油、液压油、钻探油、飞机和其它透平油、润滑脂、齿轮油、压缩机油、功能流体和其它工业和机器润滑油应用。期望与本发明多羟基酯成分一起使用的润滑油包括润滑粘度的矿物的和合成的烃油和它们与其它合成油的混合物。合成的烃油包括长链烷,诸如十六烷,烯烃聚合物,诸如己烯、辛烯、癸烯和十二烯等的低聚物。其它合成的油包括(1)完全酯化的酯油,没有自由羟基,诸如,有2-20个碳原子的单羧酸的季戊四醇酯,有2-20个碳原子的单羧酸的三羟甲基丙烷酯,(2)聚缩醛和(3)硅氧烷流体。在合成酯中特别有用的是那些由多元羧酸和单羟基醇生成的酯。更优选由完全酯化的季戊四醇或其与二和三季戊四醇的混合物与有1-20个碳原子的脂族单羧酸或这些酸的混合物制备的酯流体。
在一些上述润滑油配方中可根据特别的用途使用溶剂。可以使用的溶剂包括烃溶剂,诸如甲苯、苯、二甲苯等。
根据本发明配制的润滑油优选含有约60-99%(重量)至少一种本发明的多羟基酯成分,约1-20%(重量)润滑油添加剂成分,约0-20%(重量)溶剂。可选择地,基料含有1-50%(重量)至少一种选自下列的另外的基料:矿物油、高精炼的矿物油、烷基化的矿物油、聚α-烯烃、聚(亚烷基)二醇、磷酸酯、硅油、二酯和多羟基酯。
曲轴箱润滑油
本多羟基酯成分可以在用于火花点燃的和压缩点燃的曲轴箱润滑油配方中(即,旅行车发动机油、重型柴油发动机油、旅行车柴油)使用。下列添加剂一般以这样的量使用,从而提供他们正常的伴随功能。各成分的一般量也表示如下。所有列出的值均以活性成分的质量百分比表示。
添加剂 | %(质量)(宽的) | %(质量)(优选的) |
无灰分散剂 | 0.1-20 | 1-8 |
金属去垢剂 | 0.1-15 | 0.2-9 |
腐蚀抑制剂 | 0-5 | 0-1.5 |
金属二烃基二硫代磷酸酯 | 0.1-6 | 0.1-4 |
补充的抗氧化剂 | 0-5 | 0.01-1.5 |
倾点下降剂 | 0.01-5 | 0.01-1.5 |
消泡沫剂 | 0-5 | 0.001-0.15 |
补充的抗磨剂 | 0-0.5 | 0-0.2 |
摩擦改性剂 | 0-5 | 0-1.5 |
粘度改性剂 | 0.01-6 | 0-4 |
合成的和/或矿物的基料 | 余量 | 余量 |
可用任何适宜的方法将各添加剂混入基料中。这样,用在基料中以理想水平的浓度分散或溶解每种成分可将其直接加入基料中。这种混合可在环境温度或提高的温度进行。
优选除了粘度改进剂和倾点下降剂之外的所有添加剂可作为添加组分混入浓缩液或这里所述的添加组分中,继而混入基料中制成最终润滑剂。这类浓缩液的使用是常规的。一般配制的浓缩液含有恰当量的添加剂,使得当浓缩液与预定量基本润滑剂混合时能在最终配方提供理想浓度。
优选根据在US-A-4938880中所述的方法制备浓缩液。该专利描述了在至少约100℃的温度预混无灰分散剂和金属去垢剂来制备一种预混合物。此后,预混物冷却到至少85℃再加入另外的成分。
最终的曲轴箱润滑油配方可用2-20%(质量)、优选5-10%(质量)、典型地约7-8%(质量)的浓缩液或添加成分,余量为基料。
无灰分散剂包括油溶性的具有能结合被分散颗粒的官能团的聚合烃主链。一般地,分散剂包括胺、醇、酰胺或酯极性部分,其与聚合物主链经常通过一个桥基相连。例如,无灰分散剂可以选自被单和二羧酸或它们的酐取代的长链烃的油溶性盐、酯、氨基-酯、酰胺、酰亚胺和噁唑烷;长链烃的硫代羧酸酯衍生物;有多元胺与之直接相连的长链脂族烃;由长链取代的苯酚与甲醛和聚(亚烷基)多元胺缩合形成的曼尼希(Mannich)缩合产物。
粘度改性剂(VM)用于为润滑油提供高温和低温可操作性。使用的VM可具有单功能,或可具有多功能。
多功能粘度改性剂还可作为分散剂也是已知的。适合的粘度改性剂是聚异丁烯、乙烯和丙烯和较高α-烯烃的共聚物、聚甲基丙烯酸酯、聚甲基丙烯酸烷基酯、甲基丙烯酸酯共聚物、不饱和的二羧酸和乙烯基化合物的共聚物、苯乙烯和丙烯酸酯的共聚合物、部分氢化的苯乙烯/异戊二烯共聚物、苯乙烯/丁二烯部分氢化共聚物和异戊二烯/丁二烯部分氢化共聚物以及部分氢化的丁二烯和异戊二烯和异戊二烯/二乙烯基苯的均聚物。
含金属或形成灰的去垢剂的功能是作为减少或除去沉淀的清洁剂和作为酸中和剂或腐蚀抑制剂,从而降低磨损和腐蚀并延长机器寿命。清洁剂一般含有一个极性的头和长疏水性的尾,极性的头含有酸性有机化合物的金属盐。盐可含有基本上化学计算量的金属,其中它们是通常被称为常规或中性盐,一般具有总碱数(TBN)--可用ASTM D-2896测量--为0-80。通过将诸如氧化物或氢氧化物的过量金属化合物与诸如二氧化碳的酸性气体反应使包括大量的金属碱成为可能。生成的过碱化的清洁剂包括作为金属碱(例如碳酸盐)微粒的外层的中和的清洁剂。这种过碱化的清洁剂可具有150或更多的TBN,一般为250-450或更多。
可以使用的清洁剂包括油溶性中性的和过碱化的金属磺酸盐、酚盐、硫化的酚盐、硫代磷酸盐、水杨酸盐、环烷酸盐和另外的油溶性羧酸盐、特别是碱金属或碱性金属--例如钠、钾、锂、钙和镁的盐类。最常用的金属是钙和镁,两者均可存在于在润滑剂中使用的清洁剂中,以及钙和/或镁与钠的混合物也是最常用的。特别合适的金属清洁剂是中性的和过碱化的TBN为20-450TBN的磺酸钙,以及TBN为50-450的中性和过碱化的酚钙和硫化的酚盐。
二烃基二硫代磷酸酯金属盐经常作为抗磨损和抗氧化剂使用。金属可以是碱金属或碱土金属,或铝、铅、锡、钼、锰、镍或铜。锌盐是在润滑油中最常用的,用量为0.1-10、优选0.2-2%(重量),以润滑油成分的总重量为基计。可根据已知技术制备它们,首先形成二烃基二硫代磷酸(DDPA),通常通过一种或多种醇或一种酚与P2S5反应,然后用一种锌化合物中和生成的DDPA来制备。例如,可通过伯醇和仲醇的混合物反应制备二硫代磷酸。另一选择是,当一者的烃基的特征是完全为仲而另一者的烃基的特征是完全为伯时可制备多二硫代磷酸。为制备锌盐,可以使用任何碱性或中性锌化合物,但氧化物、氢氧化物和碳酸盐是最常使用的。由于在中和反应中使用了过量的碱性锌化合物,工业添加剂经常含有过量的锌。
氧化抑制剂或抗氧化剂降低使用中的基料的变质趋势,变质可表现为氧化的产物--诸如在金属表面上的淤渣和清漆状沉淀--和粘度增加。这类氧化抑制剂包括位阻的酚类、优选具有C5-C12烷基侧链的烷基苯酚硫代酯的碱土金属盐、壬基苯酚硫化钙、无灰油溶性酚盐和硫化的酚盐、磷硫化的或硫化的烃、含磷酯、金属硫代氨基甲酸盐、在US-A-4867890中所述的油溶性铜化合物和含钼化合物。
可包括摩擦改性剂以改进燃料更经济。已知油溶性烷氧化的单胺和二胺可改进边界层润滑。可使用胺本身或以加合物形式或与一种硼化合物--诸如硼酸、卤化硼、偏硼酸盐、硼酸或一种单-、二-或三-烷基硼酸酯--的反应产物。
其它摩擦改进剂是已知的。在这些中有羧酸和酐与醇反应形成的酯。其它适合的摩擦改进剂一般包括一个极性端基(例如羧基或羟基),其共价地键连到一亲油的烃链上。在US-A-4702850中描述了羧酸和酐与醇的酯。M.Belzer在“摩擦学期刊”(Journal of Tribology)(1992).114卷675-682页和M.Belzer与S.Jahanmir在“润滑科学”(LubricationScience)(1988)1卷3-26页描述了其它合适的摩擦改进剂的例子。这类例子之一是有机金属钼。
可以使用选自非离子聚氧亚烷基多元醇和其酯、聚氧亚烷基酚类和阴离子烷基磺酸的防锈剂。
可使用含铜和铅的防腐蚀剂,但在本发明的配方中一般不需要。一般这类化合物是含5-50个碳原子的噻二唑多硫化物、其衍生物和其聚合物。一般是1,3,4-噻二唑衍生物,诸如那些在美国专利2719125、2719126和3087932中描述的。其它类似的材料是在美国专利3821236、3904537、4097387、4107059、4136043、4188299和4193882中描述的。其它添加剂是噻二唑的硫代和多硫代亚磺酰胺,诸如那些在GB-1560830中描述的。苯并***衍生物也在这类添加剂的范围中。当润滑成分中包括这些化合物时,其优选以不超过0.2%(重量)活性成分的量存在。
可使用少量破乳成分。优选的破乳成分在EP-330522中描述。其通过烯化氧与由双-环氧化物与多羟基醇反应得到的加合物反应制备。应以不超过0.1%(质量)活性成分的量使用破乳剂。0.001-0.05%(质量)活性成分的处理率是适宜的。
倾点下降剂也称为润滑油流动改进剂,降低流体流动或可被倾倒的最低温度。这类添加剂是公知的。改进流体低温下流动性的那些添加剂一般是C8-C18二烷基富马酸酯/乙酸乙烯酯共聚物、聚甲基丙烯酸烷基酯等。
可用许多化合物控制泡沫,包括聚硅氧烷型消泡剂,例如硅油或聚二甲基硅氧烷。
一些上述添加剂可有多种效能;例如,一种添加剂可作为分散剂-氧化抑制剂。这种方法是公知的,无需进一步详述。
双冲程引擎油
多羟基酯成分可与选择的润滑剂添加剂一起用于双冲程引擎油配方中。优选的双冲程引擎油一般用根据本发明形成的多羟基酯成分和任何常规的双冲程引擎油添加成分一起配制。一般下列添加剂以这样的量使用从而提供它们常规的附带的功能。添加成分可包括--但不限于--粘度指数改进剂、防腐蚀剂、氧化抑制剂、偶合剂、分散性、耐恃压剂、颜色稳定剂、表面活性剂、稀释剂、去垢剂和锈抑制剂、倾点下降剂、消泡剂和抗磨损剂。
根据本发明的双冲程引擎油一般可使用约75-85%基料,约1-5%溶剂,余量包括一种添加成分。
用于润滑剂的上述添加剂的例子在下列文件中说明,这些文件在此引用参考:US-A-4663063(Davis),1987年5月5日公开;US-A-5330667(Tiffany,Ⅲ等人),1994年7月19日公开;US-A-4740321(Davis等人),1988年4月26日公开;US-A-5321172(Alexander等人),1994年6月14日公开;US-A-5049291(Miyaji等人),1991年9月17日公开。
发射器油
发射器是一种设备,用于海上***上将飞机弹射离开***。多羟基酯成分可与选择的润滑剂添加剂一起用于发射器油的配方。优选的发射器油一般用根据本发明形成的多羟基酯和任何常规的发射器油添加成分一起配制。一般下列添加剂以这样的量使用从而提供其常规的附带的功能。添加成分可包括--但不限于--粘度指数改进剂、防腐蚀剂、氧化抑制剂、耐特压剂、颜色稳定剂、去垢剂和生锈抑制剂、消泡剂、抗磨损剂和摩擦改性剂。Klamann在“润滑剂和相关产品”(Lubricants andRelated Products),Verlag Chemie,Deerfield Beach,FL,1984公开了这些添加剂,上述文献在此引用参考。
根据本发明的发射油一般可使用约90-99%基料,余量包括一种添加成分。
液压油
多羟基酯成分可与选择的润滑剂添加剂一起用于液压油的配制。优选的液压油一般用根据本发明形成的多羟基酯成分和任何常规的液压油添加成分配制。下列添加剂一般以这样的量使用从而提供它们常规的附带的功能。添加成分可包括--但不限于--粘度指数改进剂、防腐蚀剂、边界润滑剂、破乳剂、倾点下降剂和消泡剂。
根据本发明的液压油一般可使用约90-99%基料,余量含有一种添加成分。
其它添加剂在1988年11月8日公开的US-A-4783274(Jokinen等人)中公开,该文献在此引用参考。
钻探油
多羟基酯成分可与选择的润滑剂添加剂一起用于钻探油配方中。优选的钻探油一般用根据本发明形成的多羟基酯成分和任何常规的钻探油添加成分配制。下列添加成分一般以这样的量使用,从而提供它们常规的附带的功能。添加剂包括--但不限于--粘度指数改进剂、防腐蚀剂、湿润剂、水损失改进剂、杀菌剂和钻头润滑剂。
根据本发明的钻探油一般可使用约60-90%基料和约5-25%溶剂,余量含有一种添加成分。见1983年5月3日公开的US-A-4382002(Walker等人),该文献在此引用参考。
适合的烃溶剂包括:矿物油,特别是那些沸程200-400℃有良好氧化稳定性的石蜡基油,诸如Mentor 28Exxon Chemical Americas,Houston,Texas出售;柴油和汽油;重芳族萘。
透平油
多羟基酯成分可与选择的润滑剂添加剂一起用于透平油的配方中。优选的透平油一般用根据本发明形成的多羟基酯成分和任何常规的透平油添加成分配制。下列添加成分一般以这样的量使用,从而提供它们常规的附带的功能。添加成分包括--但不限于--粘度指数改进剂、防腐蚀剂、氧化抑制剂、增稠剂、分散剂、抗乳化剂、颜色稳定剂、去垢剂和生锈抑制剂和倾点下降剂。
根据本发明的透平油一般可使用约65-75%基料和约5-30%溶剂,余量含有一种添加成分,一般在约0.01-5.0%(重量),基于组合物总重量计。
润滑脂
多羟基酯成分可与选择的润滑剂添加剂一起用于润滑脂的配方中。在润滑脂中主要成分是增稠剂或凝胶剂,在不同的润滑脂配方中通常都包括这种成分。除了增稠剂或凝胶剂,通过可用的特别的润滑基料和各种添加剂可影响润滑脂的其它性能和特点。
优选的润滑脂一般由根据本发明形成的多羟基酯成分和任何常规的润滑脂添加成分一起配制。下列添加成分一般以这样的量使用,从而提供它们常规的附带的功能。添加成分可包括--但不限于--粘度指数改进剂、氧化抑制剂、耐特压剂、去垢剂和生锈抑制剂、倾点下降剂、金属钝化剂、抗磨损剂和增稠剂或凝胶剂。
根据本发明的润滑脂一般可用约80-95%基料和约5-20%增稠剂或凝胶剂,余量含有一种添加成分。
在润滑脂配方中使用的典型增稠剂包括碱金属皂、粘土、聚合物、石棉、碳黑、硅胶、聚脲和铝配合物。皂稠化的润滑脂中以最平常的锂和钙皂为最常用。由长链脂肪酸的碱金属盐与12-羟基硬脂酸锂生成简单皂润滑脂,突出的一种是由12-羟基硬脂酸、氢氧化锂一水合物和矿物油形成。复合皂润滑脂也是常用的,含有有机酸混合物的金属盐。现在使用的一种典型的复合皂润滑脂是由12-羟基硬脂酸、氢氧化锂一水合物、壬二酸和矿物油生成的复合锂皂润滑脂。在许多专利中描述例举了锂皂,包括1973年9月11日公开的US-A-3758407(Harting);1974年2月12日公开的US-A-3791973(Gilani);1975年12月30日公开的US-A-3929651(Murray),所有这些与1983年7月12日公开的US-A-4392967(Alexander)一起在此引用参考。
在润滑脂中使用的添加剂的描述可在Boner“现代润滑脂”(ModernLubricating Greases)1976,第5章找到,该文献在此引用参考,还有上述在其它产品中所列的添加剂。
压缩机油
多羟基酯成分可与选择的润滑油添加剂一起用于压缩机油的配方中。优选的压缩机油一般由根据本发明形成的多羟基酯成分和任何常规的压缩机油添加成分一起配制。下列添加成分一般以这样的量使用,从而提供它们常规的附带的功能。添加成分可包括--但不限于--氧化抑制剂、增溶剂、防锈剂/金属钝化剂、破乳剂和抗磨损剂。
根据本发明的压缩机油一般可使用约80-99%基料和约1-15%溶剂,余量含有一种添加成分。
用于压缩机油的添加剂在1992年10月20日公开的US-A-5156759(Culpon,Jr.)中说明,该文献在此引用参考。
在许多润滑剂应用--诸如航空透平油--中极为重要的是提供一种热/氧化稳定的润滑剂产品。一种测定润滑剂相对热/氧化稳定性的方法是用高压差示扫描量热法(HPDSC)。在这个试验中,将样品加热到一个固定温度并在一定空气(或氧气)压力下保持该温度,测定开始分解的时间。分解时间越长,样品越稳定。在此后所有的情况中,条件如下,除非另有特别注示:220℃,3.445Mpa(500psi)空气(即0.689MPa)(100psi)氧和2.756MPa(400psi)氮气),加0.5%(重量)二辛基二苯基胺(Vanlube-81作为抗氧化剂。
实施例1
为了比较,下表1对照常规的非多羟基酯说明在碳链上没有未转化羟基分布的多羟基酯成分的提高的热/氧化性能。
表1
HPDSC分解时间样品号 酯* 分钟
1 TMP/C7/C9/TMH 23.9
2 TMP/C7/C810 23.4
3 二异庚基己二酸酯 11.6
4 二异辛基己二酸酯 9.7
5 二异癸基己二酸酯 6.0
6 二(十三基)己二酸酯 3.9
7 异辛基邻苯二甲酸酯 8.0
8 (十三基)邻苯二甲酸酯 10.2*有0.5%(重量)二辛基二苯基胺抗氧化剂。TMP表示三羟甲基丙烷。C7是线性C7酸。C9是线性C9酸。TMH是3,5,5-三甲基己酸。C810是3-5%(摩尔)n-C6酸,48-58%(摩尔)n-C8酸、36-42%(摩尔)n-C10酸和0.5-1.0%(摩尔)n-C12酸的混合物。
下表2中的数据表明如HPDSC试验所测定的多羟基酯的热/氧化性能有明显提高范围。特别应注意到3,5,5-三甲基己酸和2,2-二甲基丙酸(即,新戊酸(neoC5)在HPDSC试验中特别稳定。
表2
HPDSC分解时间样品号 酯* 分钟
9 TMP/n-C9 14.2
10 TechPE/n-C9 14.7
11 TMP/TMH 119
12 TechPE/TMH 148
13 MPE/TMH 143
14 TMP/n-C5 51.9
15 50%TMP/TMH和50%TMP/n-C5 65.7
16 MPE/TMH/neo-C5 168*有0.5%(重量)二辛基二苯基胺抗氧化剂。n-C9是线性常规C9酸。TechPE是工业级季戊四醇(即,88%单季戊四醇、10%二季戊四醇和1-2%三季戊四醇。MPE是单季戊四醇。n-C5是线性常规C5酸。TMH是3,5,5-三甲基己酸。neo-C5是2,2-二甲基丙酸。
分布了未转化羟基的多羟基酯由工业级季戊四醇和3,5,5,-三甲基己酸(样品18)通过混合约225%摩尔当量3,5,5,-三甲基己酸与1摩尔工业级季戊四醇生成。其在下表3中与由工业级季戊四醇和3,5,5-三甲基己酸(样品17)使用过量3,5,5-三甲基己酸制备的常规多元醇酯比较。
表3
HPDSC分解时间样品号 酯* 分钟
17 TechPE/TMH 148
18 TechPE/TMH w/25%未转化的OH 468TechPE是工业级季戊四醇(即约88%单季戊四醇、10%二季戊四醇和1-2%三季戊四醇)。TMH是3,5,5-三甲基己酸。*有0.5%(重量)的二辛基二苯基胺抗氧化剂。表1-3的数据支持了本发明人的发现,这种含有至少1%(摩尔)未转化羟基(OH)的多羟基酯成分经高压差示扫描量热法(HPDSC)测定与常规多元醇和非多元醇酯相比具有令人吃惊的提高的热/氧化稳定性。
样品17和18的氧化诱导时间之间的不同表现出高羟基数酯对二辛基二苯基胺的性能的协同效果。鉴于由三甲基己酸衍生的工业级季戊四醇的全酯的诱导时间是148分钟,468分钟表现出抗氧化剂和高羟基数酯的联合效果。差值(即320分钟)是协同效果并且是在接枝的加合物中期望出现的。
实施例2
含有至少1%(摩尔)未转化羟基的多羟基酯在HPDSC试验中与三羟甲基丙烷和线性酸的多羟基酯(7810)相比在热/氧化性能方面表现出很大的提高。这些酯含有支化的特定型式,三羟甲基丙烷(TMP)和季戊四醇(单级和工业级)酯都有提高。下表4总结了本发明人得到的结果。
表4
HPDSC分解时间样品号 酯 羟基数 分钟1 TMP/2EH 20 30.12 TMP/2EH 64.0 225.33 TMP/2EH 75.0 125.34 MPE/2EH 12.1 24.45 MPE/2EH 63.8 183.56 TechPE/2EH 3.6 17.57 TechPE/TMH <10 1488 TechPE/TMH 86 2689 TechPE/TMH 68.5 36410 TechPE/TMH >50 46811 TMP/7810 0.2 26.112 TMP/7810 25.7 21.313 TMP/7810 26.8 22.914 TMP/7810 43.5 21.315 TMP/7810 73.8 26.5羟基数用常规近红外技术在mg KOH/克样品中测定。2EH是2-乙基己酸。TechPE是工业级季戊四醇(即88%单季戊四醇、10%二季戊四醇和1-2%三季戊四醇)。MPE是单季戊四醇。TMH是3,5,5-三甲基己酸。TMP是三羟甲基丙烷。7810是37%(摩尔)n-C7酸和63%(摩尔)3-5%(摩尔)n-C6酸、48-58%(摩尔)n-C8酸、36-42%(摩尔)n-C10酸和0.5-1.0%(摩尔)n-C12酸的混合物。
上述表4和图1的结果表明当所有最初加入的抗氧化剂(Vanlube-81)消耗时,酯自由基不恢复,真正的分解迅速发生,如样品号1、4和6所示,其含有少量未转化的羟基,在由线性酸形成的多羟基酯中也存在可忽略量的未转化羟基(见样品号11-15)。与支化的酯--诸如上述样品号2、3和6-10-一起,未转化的羟基(即,全酯唯一的分子变化)能将其氢原子传递给首先生成的自由基,从而生成一个更稳定的自由基,起到另外的抗氧化剂的作用。与在上述样品号11-15中表明的线性酸一起,烷基链氧化的速率比·OOH生成的速率快,所以高羟基酯不抑制氧化。上表4的结果在附图1中用图表示。
实施例3
下表5中所示的数据证明由多元醇和支化的酸根据本发明生成的具有未转化羟基的多羟基酯成分表现出内部抗氧化剂性能。
表5
HPDSC分解时间样品号 酯 羟基数 分钟1 TechPE/TMH 大于50 468有0.5%V-812 TechPE/TMH 大于50 58.3没有V-813 TechPE/L9 小于5 16.9有0.5%V-814 TechPE/TMH 小于5 148有0.5%V-815 TechPE/TMH 小于5 3.14没有V-81V-81是二辛基二苯基胺。TechPE是工业级季戊四醇(即,88%单季戊四醇、10%二季戊四醇和1-2%三季戊四醇)。TMH是三甲基己酸。L9是62-70%(摩尔)线性C9酸和30-38%(摩尔)支化的C9酸的混合物。
上表5中的结果表明,与常规的不含任何明显量的自由或未转化羟基的多元醇酯相比,有未转化羟基的多羟基酯(即样品号1和2)将润滑剂配方的氧化诱导时间极大地提高了。另外,将这些独特的多羟基酯与诸如V-81的一种抗氧化剂联合延长了分解所需的时间(见样品号1)。尽管当该多羟基酯不包括任何添加的抗氧化剂时分解时间减少了,与有抗氧化剂的常规C9酸多羟基酯相比,仍需约31/2倍更长的时间分解(即58.3分钟(样品2)对16.9分钟(样品3))。此外,不考虑是否有抗氧化剂与各种多羟基酯成分混合,样品4和5表明羟基数小于5的多羟基酯成分的分解比羟基数大于50的相同的酸和多元醇生成的多羟基酯成分(例如样品1和2)更迅速。这清楚地表明,如HPDSC所测定,合成在多羟基酯的碳链上有未转化羟基的多羟基酯成分为生成的产品提供了提高的热/氧化稳定性。最后,没有使用抗氧化剂的样品2和5的比较清楚地表明有大量未转化羟基键连的工业级季戊四醇和3,5,5-三甲基己酸的多羟基酯的抗氧化剂性能具有58.3分钟HPDSC,而几乎没有或没有未转化羟基的相同的多羟基酯具有3.14分钟HPDSC。
实施例4
下表6的数据表明根据本发明由多元醇和支化的酸形成的有未转化羟基(即,未转化羟基)的多羟基酯在与其它诸如聚α-烯烃(PAO)的烃基料混合时也能提高热/氧化稳定性。
表6
HPDSC分解时间样品号 基料成分 羟基数* 分钟**1 PA06 10.652 95%PAO6和5%TMP/7810 <5 12.993 90%PAO6和10%TMP/7810 <5 13.494 75%PAO6和25%TMP/7810 <5 18.305 95%PAO6和5%TechPE/TMH <5 12.896 90%PAO6和10%TechPE/TMH <5 13.527 75%PAO6和25%TechPE/TMH <5 17.038 95%PAO6和5%MPE/2EH 63.8 18.199 90%PAO6和10%MPE/2EH 63.8 28.7510 95%PAO6和5%MPE/TMH 68.5 22.5711 90%PAO6和10%MPE/TMH 68.5 53.6812 75%PAO6和25%MPE/TMH 68.5 108.86 PAO6是1-癸烯低聚物。*羟基数在mg KOH/克样品中测定,是混合物的含酯部分的羟基数。*表示HPDSC测量在190℃和3.445MPa在0.5%Vanlube-81添加剂(即二辛基二苯基胺)存在下进行。2EH是2-乙基己酸。TechPE是工业级季戊四醇(即88%单季季戊四醇、10%二季戊四醇和1-2%三季戊四醇)。MPE是单季戊四醇。TMH是3,5,5-三甲基己酸。TMP是三羟甲基丙烷。7810是37%(摩尔)n-C7酸和63%(摩尔)3-5%(摩尔)n-C6酸、48-58%(摩尔)n-C8酸、36-42%(摩尔)n-C10酸和0.5-1.0%(摩尔)n-C12酸的混合物。
在上表6和图2表明的结果表示出如HPDSC测定的当有至少10%未转化羟基的多羟基酯成分(即样品8-12)与诸如聚α-烯烃的烃基料混合时能提高热/氧化稳定性。
实施例5
下表7所示的数据表明根据本发明由多元醇和支化的酸生成的有未转化羟基的多羟基酯与0.5%Vanlube81(一种抗氧化剂)混合能如HPDSC所测定的延迟热/氧化降解的开始。下列样品在3.445MP(500psi)空气(即0.689MPa(100psi)氧气和2.756MPa(400psi)氮气)中进行测定。
表7
温度 HPDSC样品 烃 酯 比例 (℃) 羟基数 (分钟)1 SN150 MPE/2EH 95/5 190 63.5 14.532 SN150 MPE/2EH 90/10 190 63.5 22.413 SN150 MPE/2EH 75/25 190 63.5 31.944 SN150 MPE/TMH 95/5 190 68.5 16.985 SN150 MPE/TMH 90/10 190 68.5 17.586 SN150 MPE/TMH 75/25 190 68.5 57.18SN150是一种具有14-34个碳原子的低硫、中和的、饱和的线性烃。TMH是3,5,5-三甲基己酸。2EH是2-乙基己酸。MPE是单季戊四醇。
实施例6
制备下列复合酸酯,其中羟基数被调到全酯和部分酯之间。由下表8中所示数据可看出较低的转化--即羟基数大于10mg KOH/g--如HPDSC所测定的产生了较高的热/氧化稳定性。
表8复合酸 OH数 HPDSC酯 (mg KOH/g) (分钟)TMP+己二酸+Ck9 4.77 29.30TMP+己二酸+Ck9 43.50 61.07TMP+己二酸+Ck9 65.20 75.53TPE+己二酸+Ck9 6.58 35.96TPE+己二酸+Ck9 27.28 79.49TPE+己二酸+Ck9 61.52 105.97TMP代表三羟甲基丙烷TPE代表工业级季戊四醇Ck9代表3,5,5-三甲基己酸
虽然我们根据我们的发明表述了一些实施方案,本领域技术人员可清楚地理解能容易地得到许多变化。因此,我们不希望受到所表述的细节的限制,而是想表示在所附权利要求范围内所有的改变和改进。
Claims (22)
1.一种含有连接在有机主链上的伯脂族羟基的抗氧化剂,从而在氧化中就地产生能促进自由基清除剂和氢过氧化物分解剂型抗氧化剂的效能的氢过氧部分。
2.根据权利要求1的抗氧化剂,其中所述的抗氧化剂含有下述原料的反应产物:
通式R(OH)n的支化的或线性的醇,其中R是有约2-20个碳原子的脂族或环脂族基,n是至少2;和
至少一种支化的或线性的有约C2-C20范围内碳数的羧酸;其中所述抗氧化剂含有约5-180之间的羟基数。
3.根据权利要求1的抗氧化剂,其中所述的抗氧化剂由反应物衍生,从而反应产物含有未转化的-CH2OH部分。
4.根据权利要求1的抗氧化剂,其中所述的抗氧化剂由三(羟甲基)氨基甲烷和甲醛的反应产物衍生,从而生成1-氮杂-3,7-二氧杂-双环[3.3.0]辛基-5-甲醇。
5.根据权利要求1的抗氧化剂,其中所述的抗氧化剂由三(羟甲基)氨基甲烷和环己酮的反应产物衍生,从而生成2,2-五亚甲基-1,3-噁唑烷-4,4-二甲醇。
6.根据权利要求1的抗氧化剂,其中所述的抗氧化剂由三(羟甲基)氨基甲烷和线性或支化的羧酸的反应产物衍生,从而生成通式
R(C=O)NHC(CH2OH)3的酰胺,其中R是由线性或支化的酸与三羟甲基氨基甲烷的反应产物衍生的线性或支化的烷基链。
8.根据权利要求3的抗氧化剂,其中所述的未转化的羟基与易离去基团反应,从而在化学保护的衍生物水解或氧化时生成自由的-CH2OH基。
9.根据权利要求1的抗氧化剂,其中所述的抗氧化剂与至少一种选自矿物油、多羟基酯、聚α-烯烃、燃料、低聚物和高聚物的材料混合或接枝到该材料上。
10.根据权利要求1的抗氧化剂,其中所述的抗氧化剂是由至少一种线性或支化的酸与至少一种选自钛、硅、铝、镍、铁和铜的金属的反应产物形成的金属羧酸配合物。
11.一种润滑剂,由下列物质制备:
至少一种选自矿物油、精炼矿物油、烷基化的矿物油、聚α-烯烃、聚(亚烷基)二醇、磷酸酯、硅油、二酯和多羟基酯的基料;和
含有至少一种抗氧化剂的润滑剂添加组分,该抗氧化剂含有连接在有机主链上的伯脂族羟基,从而在氧化中就地产生能促进自由基清除剂和氢过氧化物分解剂型抗氧化剂的效能的氢过氧部分。
12.根据权利要求11的润滑剂,其中所述的抗氧化剂含有下述原料的反应产物:
通式R(OH)n的支化的或线性的醇,其中R是有约2-20个碳原子的脂族或环脂族基,n是至少2;和
至少一种支化的或线性的有约C2-C20范围内的碳数的羧酸;其中所述抗氧化剂含有约5-180之间的羟基数。
13.根据权利要求11的润滑剂,其中所述的抗氧化剂由反应物衍生,从而反应产物含有未转化的-CH2OH部分。
14.根据权利要求11的润滑剂,其中所述的抗氧化剂由三(羟甲基)氨基甲烷和甲醛的反应产物衍生,从而生成1-氮杂-3,7-二氧杂-双环[3.3.0]辛基-5-甲醇。
15.根据权利要求11的润滑剂,其中所述的抗氧化剂由三(羟甲基)氨基甲烷和环己酮的反应产物衍生,从而生成2,2-五亚甲基-1,3-噁唑烷-4,4-二甲醇。
16.根据权利要求11的润滑剂,其中所述的抗氧化剂由三(羟甲基)氨基甲烷和线性或支化的羧酸的反应产物衍生,从而生成通式
R(C=O)NHC(CH2OH)3
的酰胺,其中R是由线性或支化的酸与三羟甲基氨基甲烷的反应产物衍生的线性或支化的烷基链。
17.根据权利要求11的润滑剂,其中所述的抗氧化剂由三(羟甲基)氨基甲烷和线性或支化的羧酸的反应产物衍生,从而生成通式
的取代的噁唑烷,其中R是由所述线性或支化的羧酸衍生的线性或支化的烷基链。
18.根据权利要求13的润滑剂,其中所述的未转化的羟基与易离去基团反应,从而在化学保护的衍生物水解或氧化时生成自由的-CH2OH基。
19.根据权利要求11的润滑剂,其中所述的抗氧化剂与至少一种选自矿物油、多羟基酯、聚α-烯烃、燃料、低聚物和高聚物的材料混合或接枝到该材料上。
20.根据权利要求11的润滑剂,其中所述的润滑剂选自曲轴箱机器润滑油、双冲程引擎油、弹射器油、液压油、钻探油、透平油、润滑脂、压缩机油、齿轮油和功能液体。
21.根据权利要求11的润滑剂,其中所述的抗氧化剂是由至少一种线性或支化的酸与至少一种选自钛、硅、铝、镍、铁和铜的金属的反应产物形成的金属羧酸配合物。
22.一种抗氧化剂,含有至少一种合成的或天然的烃化合物,该烃化合物含有连接在有机主链上的伯脂族羟基,从而在氧化中就地产生能促进自由基清除剂和氢过氧化物分解剂型抗氧化剂的效能的氢过氧部分。
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US7615520B2 (en) * | 2005-03-14 | 2009-11-10 | Afton Chemical Corporation | Additives and lubricant formulations for improved antioxidant properties |
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US4116643A (en) * | 1976-12-20 | 1978-09-26 | Exxon Research & Engineering Co. | Amine salts of carboxylate half esters of 1-aza-3,7-dioxabicyclo [3.3.0] oct-5-yl methyl alcohols, their preparation and use as additives for gasoline and middle distillate fuels |
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