CN102066391A - 用于润滑基础原料和热塑性聚合物的亚磷酸酯稳定剂 - Google Patents
用于润滑基础原料和热塑性聚合物的亚磷酸酯稳定剂 Download PDFInfo
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- CN102066391A CN102066391A CN2009801217817A CN200980121781A CN102066391A CN 102066391 A CN102066391 A CN 102066391A CN 2009801217817 A CN2009801217817 A CN 2009801217817A CN 200980121781 A CN200980121781 A CN 200980121781A CN 102066391 A CN102066391 A CN 102066391A
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Classifications
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- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65744—Esters of oxyacids of phosphorus condensed with carbocyclic or heterocyclic rings or ring systems
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/52—Phosphorus bound to oxygen only
- C08K5/527—Cyclic esters
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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- C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
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- 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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- C10M2215/064—Di- and triaryl amines
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- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/049—Phosphite
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- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
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Abstract
如下结构代表的且适用于润滑油基础原料和热塑性聚合物的取代亚磷酸酯:其中R1是从由C1-C22烷基和C4-C22环烷基组成的组中选择的;选择R2和R3来形成C5-C18芳基;和R4和R5是从由H,C1-C22烷基,C2-C22烯基,C4-C22环烷基,和C5-C8芳基组成的组中选择的。取代亚磷酸酯可能会结合至少一种主抗氧化剂和其他添加剂。
Description
发明领域
本发明涉及作为抗氧化剂用于热塑性聚合物和润滑剂添加剂组合物的新型液态亚磷酸酯组合物。本发明涉及亚磷酸酯稳定剂组合物,其特定地包含用于润滑组合物和热塑性聚合物的固体组合物的亚磷酸酯稳定剂的添加剂共混物。
背景信息讨论
对用于润滑剂、热塑性塑料和弹性体的液体亚磷酸酯稳定剂的需求是一直存在的。当塑料、弹性体和润滑剂暴露于热和氧(空气)的条件下时会被氧化,而这样的条件却处处存在于它们的制造、运输、储备、或使用中。氧化会致使材料性质变质(变色、脆化、软化)、甚至失效。例如润滑剂氧化会形成不符合要求的氧化副产品,从而致使总酸度的增加,胶质的形成,变色,聚合反应,酸败,和/或气味。因此,可能会致使油剂指定的物理和摩擦学性质损失。那些广泛使用的传统抗氧化剂,包括芳族仲胺类抗氧化剂和酚类抗氧剂,在一定程度上有效地控制了润滑油的氧化。当需要保护的润滑剂在相对温和条件下,且没有长时间暴露在高温和污染物的条件下使用时,传统抗氧化剂的性能通常是令人满意的。众所周知,在更极端的使用环境下,尤其在催化过渡金属,例如铁,污染的环境下,润滑剂的分解率可能剧烈地增加以至于即使在更高的浓度下,上述传统胺和酚类抗氧剂也无法有效地控制氧化。
工业涡轮,比如用于发电的,需要使用高质量润滑剂。传统润滑剂,例如基于API组I/II/III基础原料和传统添加剂的初始锈蚀氧化(R&O)类型的循环油,已经成功地用于许多涡轮装置,例如,液压系统。然而,随着在更加恶劣的热和机械应力条件下使用的新型涡轮设备的出现,必须使用具有平衡添加剂包的合适涡轮润滑剂和相容的基础原料来获得最佳的抗氧化性和抗磨性。
解决上述铁-催化油氧化问题的一种有效方法是利用金属减活剂,其能抵消铁及其他过渡金属的催化作用。然而,如在EP公开No.0316610A1中所述,向润滑剂中加入金属减活剂会降低抗磨/极压试剂的重要的抗咬合和防磨损性能,这些抗磨/极压试剂是常见于润滑剂配方中的。
包含芳族仲胺和取代酚的润滑剂组合物是本领域普遍为人所知的。同样地,含有不同烷基化二苯胺和受阻酚当做主抗氧化剂的涡轮润滑剂也是已知的,例如U.S.Pat.No.6,326,336中使用了包含烷基化二苯胺和/或苯基萘基胺,和硫化烯烃和/或硫化脂肪酸和/或无灰的二硫代氨基甲酸酯和/或二硫化四烷基秋兰姆的抗氧化剂。
使用次抗氧化剂,例如有机亚磷酸酯,作为不同润滑材料的稳定剂也是已知的。并且包括有机亚磷酸酯和取代酚或芳族仲胺的这些润滑剂组合物也同样是已知的。
U.S.Pat.No.3,556,999公开了液压油组合物,特定地是自动传动液组合物,其包含主要量的润滑油和少量的(A)亚磷酸酯或二取代磷酸酯,(B)取代酚或芳族仲胺和(C)含N-乙烯基-2-吡咯烷酮的油溶性分散剂共聚物中的任一种。
U.S.Pat.No.3,652,411公开了聚二醇基础润滑剂,这种基础润滑剂中含少量比例且作为稳定剂的混合物,混合物包含:取代胺,脂肪族取代的酚,和有机磷酸酯,多羟基醌,苯并三唑,胺盐和取代有机亚磷酸酯。
U.S.Pat.No.3,923,672公开了据称适用在蒸汽轮机或燃气轮机中的润滑油组合物。涡轮机油组合物包含主要量的矿物或合成烃基础油和有效量的下列材料组合:亚磷酸三苯酯或三烷基取代苯基亚磷酸酯;二苯胺或烷基化二苯胺;苯基α-萘胺,苯基β-萘胺,烷基或烷芳基取代的苯基α-萘胺,或烷基或烷芳基取代的苯基β-萘胺;苯并三唑或烷基取代苯并三唑;烷基或烯基琥珀酸酐的部分酯。优选地,涡轮机油组合物额外地包含有效量的N-乙烯基-2-吡咯烷酮和α-烯烃的共聚物。
U.S.Pat.No.4,652,385公开了低挥发性三取代亚磷酸酯和低挥发性空间位阻的酚类稳定剂的润滑剂组合物,其可以向选自加氢油,聚α-烯烃油和链烷白油,和它们的混合物的润滑油提供有效的抗氧化性。
U.S.Pat.No.5,124,057公开了低挥发性三取代亚磷酸酯和选择的取代异氰脲酸酯酚类稳定剂的润滑剂组合物,其可以向选自加氢油,聚α-烯烃油,链烷白油和它们的混合物的润滑油提供抗氧化性。
U.S.Pat.No.5,232,614公开了,在长时间暴露在高温的氧气后,取代对苯二胺还是可以作为抗氧化剂来有效地阻止机轴箱润滑油变浓和沉淀物形成。额外的防磨添加物例如二-和三-烷基,环烷基和芳基亚磷酸酯也被公开了。
U.S.Pat.No.5,688,847公开了具有下述分子式的氟亚磷酸酯化合物:
这些化合物在聚合物,例如聚丙烯和聚氯乙烯中作为稳定剂显示出优越性能。专利中也公开了制造这些化合物的工艺。
U.S.Pat.No.6,172,014公开了改进的降低压缩机气体泄漏的方法,这个方法中压缩缸中带有润滑剂,润滑剂中包含小于大约1%的协同抗氧化剂混合物,而这种抗氧化剂混合物包含至少一种亚磷酸酯抗氧化剂和至少一种其他的抗氧化剂。
U.S.公开No.2003/0171227公开了用于润滑基础原料和润滑剂配方的稳定剂组合物,这种稳定剂组合物是由(a)选择性地混合至少一种芳族胺的胺类抗氧剂和至少一种阻碍酚抗氧剂得到的混合物和(b)选择性地混合至少一种中性的有机磷酸酯或亚磷酸酯和至少一种酸的有机磷酸酯或亚磷酸酯得到的混合物组成的。
U.S.公开Nos.2006/0073992和2006/0069000公开了一种被稳定的润滑剂组合物,其包含润滑油和(a)至少一种有机亚磷酸酯化合物和(b)至少一种芳族仲胺或一种取代酚或它们的混合物组成的混合物。这种组合物已经被发现在所需的工作环境下具有较高的抗氧性且可以作为涡轮润滑剂使用。
U.S.公开No.2006/0223918公开了如下结构的化合物:
其中R1,R2,R3,R4,R5,和R6独立地选自烷基,且R1不同于R2。这种化合物可用做热塑性树脂的稳定剂。
国际公开No.WO2007/149143公开了一种化合物,其包含至少二种如下结构但不相同的亚磷酸酯的混合物:
其中R1,R2,和R3独立地选自烷基化的芳基且其中所述的混合物在环境条件下是液体。这种组合物具有稳定热塑性树脂和弹性体的用途。
前述公开都整体引用并包含于本文中。
发明概述
对于应用在润滑油基础原料和热塑性弹性体的液体亚磷酸酯的需要是一直持续的。本发明的第一方面中,提出了包含如下结构化合物的物质组合物:
其中R1是从由C1-C22烷基和C4-C7环烷基组成的组中选择的;选择R2和R3来形成C5-C18芳基;和R4和R5是从由H,C1-C22烷基,C2-C22烯基,C4-C22环烷基,和C5-C8芳基组成的组中选择的。在一个实施方案中,如果R5是H,则R4是从由C1-C22烷基,C2-C22烯基,C4-C22环烷基,和C5-C8芳基组成的组中选择的。任选地,烷基和烯基可能是支化的和/或环烷基和芳基可能是取代的。在优选的实施方案中,R1和R4各自独立地选自由2-乙基-己基,正辛基,和异辛基组成的组中。
本发明的第二个方面中,提供了一种制造具有如下结构化合物的方法:
其中R1是从由C1-C22烷基和C4-C22环烷基组成的组中选择的;选择R2和R3来形成C5-C18芳基;和R4和R5是从由H,C1-C22烷基,C2-C22烯基,C4-C22环烷基,和C5-C8芳基组成的组中选择的,这种方法包括:a)使磷三卤素化合物和β羟基酸化合物反应以形成卤素亚膦酸酯中间体;和b)使步骤a)中的卤素亚膦酸酯中间体和醇反应以形成该化合物。
本发明的第三方面中,提出了制备润滑油组合物的方法,这种方法包括:将至少一种选自二芳基仲胺,取代酚,和它们的共混物组成的组中的主抗氧化剂和如下结构的取代亚磷酸酯化合物混合:
其中R1是从由C1-C22烷基和C4-C22环烷基组成的组中选择的;选择R2和R3来形成C5-C18芳基;和R4和R5是从由H,C1-C22烷基,C2-C22烯基,C4-C22环烷基,和C5-C8芳基组成的组中选择的,来得到添加剂共混物;然后将此添加剂共混物加入到润滑油基础原料中。
本发明的第四方面中,提出了润滑油组合物,其包含:a)润滑油基础原料;和b)添加剂共混物,其包含:i)至少一种主抗氧化剂;和ii)由下列通式代表的取代亚磷酸酯化合物:
其中R1是从由C1-C22烷基和C4-C22环烷基组成的组中选择的;选择R2和R3来形成C5-C18芳基;和R4和R5是从由C1-C22烷基,C2-C22烯基,C4-C22环烷基,和C5-C8芳基组成的组中选择的。在一个实施方案中,基于组合物总质量的取代亚磷酸酯化合物的重量百分数(wt%)是从0.01到5wt%,例如0.1到1.5wt%。主抗氧化剂可能占组合物的总质量的0.01到5wt.%,例如0.1到1.5wt%。任选地,这种润滑油组合物也可能含有一种或多种添加剂,例如粘度指数改进剂,防腐剂,分散剂,润滑油流动改进剂,清洁剂/防锈剂,倾点抑制剂,消泡剂,抗磨剂,密封溶胀剂,摩擦改性剂,和金属减活剂。
本发明的第五方面中,提出了一种固体组合物,其包含:热塑性弹性体;和如下结构的取代亚磷酸酯化合物:
其中R1是从由C1-C22烷基和C4-C22环烷基组成的组中选择的;选择R2和R3来形成C5-C18芳基;和R4和R5是从由H,C1-C22烷基,C2-C22烯基,C4-C22环烷基,和C5-C8芳基组成的组中选择的。在一个实施方案中,热塑性弹性体包含聚乙烯,聚丙烯,聚丙烯,聚异丁烯,聚丁烯-1,聚甲基戊烯-1,聚异戊二烯,或聚丁二烯。
优选实施方案的详细说明
本发明涉及被稳定的组合物,其包含润滑基础原料或热塑性弹性体和取代亚磷酸酯化合物和主抗氧化剂的添加剂共混物。上述取代亚磷酸酯和添加剂共混物提供了优秀的抗氧化稳定性且适用于高温铁催化环境中。本发明中可作为次抗氧化剂的取代亚磷酸酯化合物,亦称氢过氧化物分解剂,是由如下通式代表的:
其中R1是从由直链或支化的C1-C22烷基和取代或未被取代的C-4-C22环烷基组成的组中选择的;选择R2和R3来形成C5-C18芳基;和R4和R5是从由氢、直链或支化的C1-C22烷基,直链或支化的C2-C22烯基,取代或未被取代的C4-C22环烷基,和取代或未被取代的C5-C8芳基组成的组中选择的。
如果R1,R4和R5基团中的一个或多个是环烷基或芳基,环烷基和芳基可能是被直链或支化的C1-C12烷基所取代的。
在一个实施方案中,本发明包含取代亚磷酸酯化合物,其中R1,R4和R5具有同样的碳原子数。在一个实施方案中,R5优选地是氢和R4不是氢。
在此使用的关于R1,R4,R5中一个或多个的烷基和在本申请中到处使用的烷基的典型例子包括,例如,含1到22个碳原子的直链或支化的烃链基,例如,正-丙基,1-甲基乙基(异丙基),正丁基,异丁基,2,2,3,3-四甲基丁基,正戊基,1,3-二甲基戊基,3-乙基-2-甲基戊基,3-乙基-3-甲基戊基,2,3,3-三甲基戊基,2,2-二甲基己基,2,3,4-三甲基戊基,正己基,1,4-二甲基己基,2,3-二甲基己基,2,5-二甲基己基,2-乙基己基,3-乙基-己基,正庚基,2-甲基庚基,3-甲基庚基,4-甲基庚基,1,5-二甲基庚基,正辛基,辛基,异辛基,壬基,癸基等等,它们的混合物和异构体,及其类似物。
在一个实施方案中,R1是直链或支化的C4-C10烷基且优选地是直链或支化的C8烷基。上述优选的C8烷基包括2-乙基-己基,正辛基,和异辛基。
在此使用的关于R1,R4,R5中一个或多个的环烷基和在本申请中到处使用的环烷基的典型例子包括,例如,含4到22个碳原子的取代或未被取代的环,例如,环戊基,正-乙基-环戊基,正-丙基-环戊基,正-二甲基-正-乙基戊基,正-三甲基戊基,环己基,正-甲基-环己基,正-二甲基环己基,正-乙基环己基,环庚基,正-甲基环庚基,环辛基,正-甲基环辛基等等,它们的混合物,及其类似物。
在此使用的关于R2和R3,R4,R5中一个或多个的结合芳族环和在本申请中到处使用的芳基的典型例子包括,例如,含5到18个碳原子的取代或未被取代的芳环,例如,苯基,正-甲基苯基,正-二甲基苯基,正-乙基苯基,苯甲基,萘基,四氢萘基,茚基,联苯等等,它们的混合物和异构体,及其类似物。
任选地,本发明的环烷基或芳基可能被一个或多个选自由卤素,羟基,羰基,巯基,硝基,亚硝基,硫氧基氰基等等的组的基团所取代。进一步地,环烷基或芳基可能包含一或多个杂原子例如氮,硫,或氧。
在此使用的关于R4,R5中一个或多个的烯基和在本申请中到处使用的烯基的典型例子包括,例如,含2到22个碳原子的直链或支化的烃链基,例如,丙烯基,正丁烯基,异丁烯基,戊烯基,己烯基,正庚烯基,辛烯基,异-辛烯基,壬烯,癸烯基等等,它们的混合物和异构体,及其类似物。
如上所述,当连接R2和R3形成C6芳基时,即苯基,取代亚磷酸酯化合物可能由如下结构所代表:
其中R1,R4和R5如上定义。
本发明示例性的取代亚磷酸酯包括由如下结构所代表的4-氧代-1,3-二氧杂-2-磷杂萘化合物:
其中每个C8H17可以独立地是直链或支化的烷基。
本发明的另一个示例性的取代亚磷酸酯包括由如下结构所代表的4-氧代-1,3-二氧杂-2-磷杂萘化合物:
其中R4如上定义且R5是氢。
本发明的一个实施方案中,提出了制造本发明的取代亚磷酸酯的方法,其包括先将β羟基酸(BHA)和三卤素磷反应,然后再与醇反应。适用的BHA包括如下结构代表的物质:
其中R2,R3,R4和R5如上定义。示例性的β羟基酸包括烷基化水杨酸,例如4-辛基-水杨酸。适用的三卤素磷包括三氯化磷,三氟化磷,和三溴化磷。适用的醇包括C1-C22醇,包括但不限于,2-乙基-己醇,正辛醇,辛醇,和异辛醇。
BHA和三卤素磷的反应是在氮或类似的惰性气体环境中且在标准大气压力下进行的。另外,本反应可能是在叔胺例如三乙基胺或吡啶和溶剂,例如甲苯,枯烯,苯,氯苯,二甲苯,庚烷,己烷等等的存在下进行的。釜温度被维持在-15℃到15℃,例如-10℃到10℃或0℃到5℃的温度范围。本反应可制备卤化中间体。
卤化中间体在第一步的条件下进一步地与醇反应。反应产物利用真空过滤来得到本发明的取代亚磷酸酯。
在一个实施方案中,提出了包含上述分子式I-IV的取代亚磷酸酯的添加剂共混物的组合物。本发明的添加剂共混物可能包括至少一种主抗氧化剂。可与本发明添加剂共混物共同使用的主抗氧化剂,亦称自由基清除抗氧化剂,包括胺化合物,酚类化合物,和它们的混合物。
在一个实施方案中,提出了包含上述分子式I-IV的取代亚磷酸酯添加剂共混物和至少一种胺化合物的组合物。适用的胺化合物包括那些在U.S.系列No.11/128,929中描述的化合物,且上述文章的全部内容和公开都参考引入本文中。一种适用的胺化合物可能由下述结构所代表:
R6-NH-R7
其中R6和R7独立地是具有6到100个碳原子的烃基,比如烷基,烯基,芳基,环烷基,或它们的组合。
在进一步的实施方案中,适用的胺化合物可能是下列通式所代表的二芳基仲胺化合物:
(R8)a-Ar1-NH-Ar2-(R9)b
其中Ar1和Ar2独立地是芳族烃基和R8和R9独立地是氢或烷基,烯基,环烷基,或具有6到大约100个碳原子的芳基和a和b独立地是0到3但是(a+b)不大于4。
本发明实践中适用的二芳基仲胺化合物的例子包括,但是不限制于此,二苯胺,单烷基化二苯胺,二烷基化二苯胺,三烷基化二苯胺,或它们的混合物,3-羟基二苯胺,4-羟基二苯胺,单-和/或二-丁基二苯胺,单-和/或二-辛基二苯胺,单-和/或二-壬基二苯胺,苯基-α-萘胺,苯基-β-萘胺,二庚基二苯胺,单-和/或二-(α-甲基苯乙烯基)二苯胺,单-和/或二苯乙烯基二苯胺,4-(对甲苯磺酰胺基)二苯胺,4-异丙氧基二苯胺,t-辛基化的N-苯基-1-萘胺,单-和二烷基化的叔丁基-t-辛基二苯胺,N-苯基-1,2-苯二胺,N-苯基-1,4-苯二胺,N,N′-二苯基对苯二胺,N,N′-二(萘基-2-)-对-苯二胺,N-异丙基-N′-苯基-对-苯二胺,N-(1,3-二甲基丁基)-N′-苯基-对-苯二胺,N-(1-甲基庚基)-N′-苯基-对-苯二胺,和N-环己基-N′-苯基-对-苯二胺。下列的是刚刚定义的示例性二芳基仲胺化合物,且都是可以买到的,来自Chemtura Corporation的:NaugalubeTM 438,Naugalube 438L,Naugalube 640,Naugalube 635,Naugalube 680,Naugalube AMS,Naugalube APAN,Naugard PANA,Naugalube 403,Naugalube 410,和Naugalube 420;来自Ciba-Geigy的:IrganoxTM L 06和Irganox L 57;来自R.T.Vanderbilt的:VanlubeSL,Vanlube 961,Vanlube 81,Vanlube SS,Vanlube DND;来自Albermarle的:Ethanox 4720,Ethanox 4793,Ethanox 4780。
在一个实施方案中,提出了含上述分子式I-IV的取代亚磷酸酯和至少一种酚化合物的添加剂共混物的组合物。适用的酚类化合物包括U.S.系列No.11/128,929中描述的化合物,且上述的文章的全部内容和公开都参考引入本文。上述的酚化合物包括下列通式所代表的取代酚化合物:
其中R10,R11和R12独立地是氢或具有1到100个碳原子且至少一个邻位基团包含烷基链的烃基基团,比如烷基,烯基,芳基,或环烷基。优选地,邻位烷基链包含具有异-或叔-结构的支化烷基链。
由于烃基组成的广泛变化可能,本发明适用的取代酚化合物可能包括烷基化的单苯酚;烷基化对苯二酚;羟基化的硫二苯醚;亚烷基双酚;酰基氨基酚;(β-)3,5-二-叔-4-羟基苯丙酸和单或多元醇的酯;(β-)5-叔丁基-4-羟-3-甲苯丙酸和单或多元醇的酯;β-(3,5二叔丁基-4-羟苯基)丙酸的酰胺。可用于本发明实践中的酚类抗氧剂的例子包括2,6-二叔丁基-4-甲基苯酚,2,6-二叔丁基苯酚,2-叔丁基-4,6-二甲基苯酚,2,6-二叔丁基-4-乙基苯酚,2,6-二叔丁基-4-异丁基苯酚,2,6-双(α-甲基苄基)-4-甲基苯酚和2-α-甲基苄基-4-甲基苯酚,及其类似物;2,6-二叔丁基-4-甲氧基苯酚,2,5-二叔丁基-对苯二酚和及其类似物;与甲醇,辛醇,十八醇,1,6-己二醇,新戊二醇,硫代二亚乙基二醇,二甘醇,三甘醇,季戊四醇,及其类似物酯化的3,5-二叔丁基-4-羟基苯-3-丙酸。下列的是优选的取代酚化合物的例子,且都是可以购买到的,来自Chemtura Corporation的:Naugard 431,Naugalube 531,Naugalube 38,Naugalube 15,and Naugalube 18;来自Ciba-Geigy的:IrganoxTM L 115,Irganox L 118,Irganox L 135,和Irgalube F 10A;来自Albemarle的:Ethanox 4712,Ethanox 4733,Ethanox 4735,Ethanox 4702。
回到本发明的添加剂共混物,基于添加剂共混物总重量,添加剂共混物中的本发明取代亚磷酸酯的重量百分数(wt%)最高大约99wt%,例如最高大约95wt%,最高大约90wt%,最高大约85wt%,最高大约80wt%,最高大约75wt%,最高大约70wt%,最高大约65wt%,最高大约60wt%,最高大约55wt%,最高大约50wt%,最高大约45wt%,最高大约40wt%,最高大约35wt%,最高大约30wt%,最高大约25wt%,最高大约20wt%,最高大约15wt%,或最高大约10wt%。就范围而言,基于添加剂共混物的总重量,添加剂共混物可能包含占其5到99重量百分数(wt%)的取代亚磷酸酯,例如15到80wt%,25到75wt%,20到60wt%或25到50wt%。基于添加剂共混物的总重量,添加剂共混物可能包含占其5到99wt%的主抗氧化剂,例如15到80wt%,25到75wt%,20到60wt%或25到50wt%。当使用两个主抗氧化剂的混合物时,主抗氧化剂之间的比例可能是80∶20到20∶80重量份,例如60∶40到40∶60或50∶50。一个上述的实施方案中,基于添加剂共混物的总重量,添加剂共混物可能包含占其5到50wt%的取代亚磷酸酯,5到50wt%的二芳基仲胺,和5到50wt%的取代酚。
在一个实施方案中,提出了一种组合物,其包含混合了润滑油基础原料的添加剂共混物。通常,基于组合物总重量,组合物可能包含大约35到99.99wt%,例如到85到99.5wt%或90到99wt%,的润滑油基础原料。基于组合物总重量,组合物可能同时也包含0.01到大约65wt%,例如0.5到15wt%或1到10wt%,的添加剂共混物。在上述实施方案中,基于组合物总重量,取代亚磷酸酯的量可能是0.01到5wt%,例如0.05到2wt%或0.01到1.5wt%。上述的实施方案中,基于组合物总重量,二芳基仲胺化合物的量,如存在,可能是0.01到5wt%,例如0.05到2wt%或0.01到1.5wt%。上述的实施方案中,基于组合物总重量,取代酚化合物的量可能是0.01到5wt%,例如0.05到2wt%或0.01到1.5wt%。
含有本质上由本发明的取代亚磷酸酯组成的一种抗氧化剂的添加剂共混物会具有氧化稳定性,如在185℃条件下,20-300分钟,例如30-150分钟或35-100分钟的加压差示扫描量热计(PDSC)试验测量所示。含有本质上由本发明的胺抗氧化剂和取代亚磷酸酯化合物组成的两种抗氧化剂的添加剂共混物会具有氧化稳定性,如在185℃条件下,250-400分钟,例如260-350分钟或270-325分钟的PDSC试验测量所示的。含有本质上由本发明的酚抗氧化剂和取代亚磷酸酯化合物组成的两种抗氧化剂的添加剂共混物会具有氧化稳定性,如在185℃条件下,45-100分钟,例如48-75分钟或48-60分钟的PDSC试验测量所示的。含有本质上由本发明的胺,酚抗氧化剂和取代亚磷酸酯化合物组成的三种抗氧化剂的添加剂共混物会具有氧化稳定性,如在185℃条件下,90-150分钟,例如100-125分钟或105-120分钟的PDSC试验测量所示的。任选地,含有三种抗氧化剂的添加剂共混物,其不含二月桂基亚磷酸酯。
本发明的添加剂共混物尤其适用作组分来用于到许多不同的润滑油组合物中。添加剂共混物可以用在许多具有润滑粘性的油剂中,这些油剂包括天然的和合成的润滑油和它们的混合物。添加剂共混物能用到用于火花-点火和压缩-点火内燃引擎的机轴箱润滑油剂中。组合物还可以用于煤气发动机润滑剂,蒸汽-燃气轮机润滑剂,自动传动液,齿轮润滑剂,压缩机润滑剂,金属加工润滑材料,液压油,及其他润滑油和润滑脂组合物中。
通常,100℃时,润滑油基础原料是具有运动粘度为大约2到大约200厘沲(cSt),例如大约3到大约150cSt,或大约3到大约100cSt的任一天然或合成润滑油基础原料馏分。润滑基础原料是由天然润滑油剂,合成润滑油剂,或它们的混合物衍生而来。适用的润滑油基础原料包括由合成蜡和蜡异构化得到的基础原料,和由氢化裂解(而非溶剂萃取)原油的芳族和极性组分生成的基础原料然后再加氢裂化而得到的基础原料。天然润滑油剂包括动物油,例如猪油,牛脂油,植物油(例如,介花油,蓖麻油,向日葵油),石油,矿物油,和来源于煤或页岩的油。
合成油包括烃类油和卤代烃类油,例如聚合和互聚的烯烃,由费-托技术制备的气体到液体,烷基苯,多苯基,烷基化二苯醚,烷基化二苯硫醚,和它们的衍生物,类似物,同系物,及其类似物。合成润滑油也包括烯化氧聚合物,互聚物,共聚物,和它们的衍生物,其中末端羟基是被酯化,醚化等等改性过的。
另一个适用的合成润滑油系列包含多种醇和二羧酸的酯。可用做合成油的酯也包括那些由C5到C18一元羧酸和多元醇和多元醇醚合成的酯。其他的可用做合成油的酯包括从α-烯烃和二羧酸的共聚物制备的那些,其是由短或中链长醇酯化的。
硅基油,例如多烷基-,多芳基-,多烷氧基-,或芳氧基-硅氧烷油和硅酸酯油,是另一种可用的合成润滑油。其他的合成润滑油包括含磷的酸,聚合的四氢呋喃,聚α-烯烃,及其类似物的液体酯。
润滑油可能是从未精炼,精炼,二次精化油,或它们的混合物衍生的。未精炼油是直接地从天然资源或合成资源(例如,煤,页岩或焦油和沥青)中得到的,且无进一步地提纯或处理。未精炼油的例子包括直接地从干馏操作得到的页岩油,直接地从蒸馏得到的石油,或直接地从酯化加工得到的酯油,且它们每一个都无进一步地处理加工。精炼油类似于未精炼的油,但精炼油进行了一步或多步提纯来改进其一种或多种性质。适用的提纯方法包括蒸馏,加氢处理,脱蜡溶剂萃取,酸或碱萃取,过滤,渗滤等等,所有的这些方法都是本领域的技术人员所熟知。二次精化油通过加工精炼油得到的,处理工艺类似于制得精炼油的工艺方法。二次精化油亦称为回收或再加工油,其经常被进一步加工来去除废添加剂和油分解产物。
由蜡的加氢异构化获得的润滑油基础原料也可单独地或和上述天然和/或合成基础原料共同使用。这样的蜡异构油是由天然或合成蜡或它们的混合物在加氢异构化催化剂下加氢异构化生成的。天然蜡代表性地是由矿物油溶剂脱蜡回收得到的蜡膏;合成蜡代表性地是由费-托法制备的蜡。制备的异构产物代表性地经由溶剂脱蜡和分馏法来回收具有比粘度范围的各种馏分。蜡异构体的特性是拥有非常高粘度指数,通常具有至少130的粘度指数,优选地至少135或更高,和随后的脱蜡,大约-20℃或更低的倾点。
用于本发明实践的润滑油可以从组I-V中的基础原料选择,这些组在美国石油组织(API)基础原料互换性方针中广泛地说明过。这五个基础原料组记录在表1中。
回到添加剂共混物,在一个实施方案中,组合物包含添加剂共混物,该添加剂共混物包含取代亚磷酸酯和至少一种主抗氧化剂和选自粘度指数改进剂,防腐剂,分散剂,润滑油流动改进剂,清洁剂/防锈剂,倾点抑制剂,消泡剂,抗磨剂,密封件泡涨试剂,摩擦改性剂,和金属减活剂组成的组中的一种或多种额外的添加剂。基于实施方案组合物的总重量,各个添加剂典型的重量百分数,如果存在的话,列于表2。
添加剂可能单独地或组合一起使用。如表2所示,含本发明的取代亚磷酸酯和至少一种主抗氧化剂的添加剂共混物可与其他的用于润滑油的添加剂,和其他抗氧化剂一起使用。需理解的是不同实施方案设想包括添加剂共混物,该添加剂共混物包含少于所有的表2中的组分。例如,添加剂共混物可能包含取代亚磷酸酯,二芳基仲胺,缓蚀剂,倾点抑制剂,和摩擦改性剂。此外,例如,添加剂共混物可能包含取代亚磷酸酯,取代酚,粘度指数改进剂,分散剂,清洁剂/防锈剂,密封溶胀剂和摩擦改性剂。这些例子和其他的组合也是包括在本发明范畴内的,其可作为添加剂共混物来组合润滑油基础原料或热塑性塑料聚合物。U.S.Pat.No.5,498,809发明了可用的润滑油组合物添加剂,其也全文引用合并于本文中。
当其他的添加剂用于添加剂共混物时,虽然并不是必不可少的,但这样可能是理想话的情况来制备包含本发明目标抗氧化剂混合物浓缩液或分散相的添加剂和表2中的一种或多种其他上述添加剂的添加剂共混物,因此几种不同的添加剂可以同时到基础原料中从来制备润滑组合物。添加剂浓缩物在润滑油中的溶解可以用溶剂和适度加热下的混合搅拌来促进,但是这些都不是必不可少的。添加剂共混物中添加剂的含量需保证其在添加剂共混物和预定量的润滑基础原料混合后的配方中能达到所需的浓度。因此,本发明的添加剂共混物可以连同其他所需的添加剂一起加入到少量的润滑剂基础原料或其他相容的溶剂中来制备添加剂共混物,这种添加剂共混物中所含活性成分的共同量,按质量比,典型地,大约2.5到大约90wt%,例如大约15到大约75wt%,或大约25到大约60wt%,的适量的添加剂,且其余部分为基础原料。最终配方中典型的含大约0.5到20wt%的添加剂共混物,其余的为基础原料。
粘度指数(V.I.)改进剂的例子包括烯烃共聚物,分散剂烯烃共聚物,乙烯-α-烯烃共聚物,其中α-烯烃可能是丙烯,1-丁烯,或1-戊烯,或它们的氢化物,聚异丁烯或它的氢化物,苯乙烯-二烯氢化共聚物,苯乙烯-马来酸酯酸酐共聚物,和聚烷基苯乙烯,及其类似物。
防腐剂的例子包括胺螯合物,基于苯并三唑-,甲苯基三唑-,噻二唑-,和咪唑-的化合物,及其类似物。下列是示例性的防腐剂且可从King Industries,Inc.:K-CorrTM 100A2商业获得。
分散剂的例子包括聚异丁烯琥珀酰亚胺,聚异丁烯琥珀酸酯,曼尼希碱无灰分散剂,及其类似物。
润滑油流动改进剂的例子包括二烷基富马酸酯-醋酸乙烯酯共聚物及其类似物。
清洁剂的例子包括金属和无灰烷基酚酯,金属和无灰烷基酚酯,金属和无灰硫化烷基酚酯,金属和无灰烷基磺酸酯,金属和无灰烷基水杨酸酯,金属和无灰水杨醇衍生物,及其类似物。防锈剂的例子是聚乙二醇多元醇,苯并三唑衍生物,及其类似物。
倾点抑制剂的例子是聚甲基丙烯酸酯,及其类似物。
消泡剂的例子包括聚硅氧烷,硅树脂例如二甲基硅酮油和氟硅酮,及其类似物。下列是示例性的消泡剂且可从Munzing/Ultra:Foam BanMSTM 575商业获得。
可以和本发明添加剂组合使用的防磨剂的例子包括有机硼酸酯,有机亚磷酸酯,有机磷酸盐,包含有机硫化合物,硫化烯烃,硫化脂肪酸衍生物酯),氯化石蜡,二烷基二硫化磷酸锌,二芳基二硫化磷酸锌,二烷基二硫化磷酸酯,二芳基二硫代磷酸盐酯,磷硫化的烃类,及其类似物。下列是示例性的上述添加剂,且可从Lubrizol公司:Lubrizol 677A,Lubrizol 1095,Lubrizol 1097,Lubrizol 1360,Lubrizol1395,lubrizol 5139,lubrizol 5604和从Ciba-Geigy:Irgalube 353商业获得。
密封溶胀剂的例子包括芳族化合物,基于硫的化合物及其类似物。
摩擦改性剂的例子包括脂肪酸酯和氨化物,有机钼化合物,二烷基二硫代氨基甲酸钼,二烷基二硫代磷酸钼,二硫化钼,二烷基二硫代氨基甲酸三钼群,非硫钼化合物及其类似物。下列是示例性的钼添加剂,且可从R.T.Vanderbilt Company,Inc.商业获得:MolyvanTM A,Molyvan L,Molyvan 807,Molyvan 856B,Molyvan 822,Molyvan 855。下列是示例性的上述添加剂,且可从Asahi Denka Kogyo K.K.商业获得:SAKURA-LUBE 100,SAKURA-LUBE 165,SAKURA-LUBE 300,SAKURA-LUBE 310G,SAKURA-LUBE 321,SAKURA LUBE 474,SAKURA-LUBE 600,SAKURA-LUBE 700。下列的也是示例性的上述添加剂,且可从Akzo Nobel Chemicals GmbH商业获得:Ketjen-OxTM 77M,Ketjen-Ox 77TS。Naugalube MolyFM也是示例性的上述添加剂,且可从Chemtura Corporation商业获得。
金属减活剂的例子包括N,N′-二亚水杨基-1,2-丙二胺,苯并三唑和它们的衍生物,和三唑和它的衍生物。下列也是示例性的上述添加剂,且可从Ciba-Geigy:IrgametTM 39商业获得。在一个实施方案中,添加剂共混物包含取代亚磷酸酯,至少一种主抗氧化剂,且基本不含金属减活剂,如,基于组合物总重量,包含小于0.05wt%的金属减活剂,例如小于0.02wt%或小于0.001wt%。
在另一个实施方案中,由于热塑性聚合物经常是在极端温度下加工和/或使用,所以取代亚磷酸酯,或包含取代亚磷酸酯的添加剂共混物尤其适用于热塑性聚合物中的,例如聚烯烃,聚碳酸酯,聚酯,聚苯醚和苯乙烯聚合物。在一个实施方案中,基于组合物的总重量,上述组合物包含大约75到99.9wt%,例如85到99.5wt%或90到99.1wt%的热塑性聚合物。组合物可能同时包含大约0.1到25wt%,例如0.5到15wt%或0.9到10%,的取代亚磷酸酯。任选地,组合物也可能同时包含大约0.1到25wt%,例如0.5到15wt%或0.9到10%的包含取代亚磷酸酯和至少一种主抗氧化剂的添加剂共混物。
单烯烃和二烯的聚合物,例如聚丙烯,聚异丁烯,聚丁烯-1,聚甲基戊烯-1,聚异戊二烯,或聚丁二烯,及环烯的聚合物,例如的环戊烯或降冰片烯,聚乙烯(可选择性地交联),例如高密度聚乙烯(HDPE),低密度聚乙烯(LDPE)和线型低密度聚乙烯(LLDPE)都能使用。这些聚合物的混合物,例如,聚丙烯和聚异丁烯,聚丙烯和聚乙烯(例如PP/HDPE,PP/LDPE)的混合物和不同种类聚乙烯(例如LDPE/HDPE)的混合物也是能使用的。同样适用的还有单烯烃和二烯互相之间或和其他的乙烯系单体之间的共聚物,例如,乙烯/丙烯,LLDPE和它的混合物与LDPE,丙烯/丁烯-1,乙烯/己烯,乙烯/乙基戊烯,乙烯/庚烯,乙烯/辛烯,丙烯/异丁烯,乙烯/丁烷-1,丙烯/丁二烯,异丁烯,异戊二烯,乙烯/烷基丙烯酸酯,乙烯/烷基异丁烯酸酯,乙烯/醋酸乙烯酯(EVA)或乙烯/丙烯酸共聚物(EAA)和它们的盐类(离聚物)和乙烯同丙烯及二烯的三元共聚物,比如己二烯,二聚环戊二烯或亚乙基降冰片烯;和上述共聚物的混合物和它们和上述聚合物的混合物,例如聚丙烯/乙烯丙烯共聚物,LDPE/EVA,LDPE/EAA,LLDPE/EVA,和LLDPE/EAA。
烯烃聚合物是,例如在齐格勒-纳塔催化剂,如,MgCl2,铬盐和它们的螯合物,硅石,硅石矾土及其类似物的条件下由烯烃聚合反应制备的。烯烃聚合物的制备也可以使用铬催化剂或单活性中心催化剂,例如,茂金属催化剂,例如,金属的戊二烯螯合物,比如Ti和Zr。如本领域熟练的技术人员很容易理解到的,本书中使用的聚乙烯聚合物,例如LLDPE,可以包含不同的共聚用单体,如,1-丁烯,1-己烯和1-辛烯共聚用单体。
聚合物可能同时也包括苯乙烯聚合物,比如聚苯乙烯,聚(对甲基苯乙烯),聚-α-甲基苯乙烯,苯乙烯或甲基苯乙烯与二烯或丙烯酸衍生物的共聚物,例如,苯乙烯/丁二烯,苯乙烯/丙烯腈,苯乙烯/烷基异丁烯酸酯,苯乙烯/马来酐,苯乙烯/顺丁烯二酰亚胺,苯乙烯/丁二烯/丙烯酸乙酯,苯乙烯/丙烯腈/甲基丙烯酸酯,由苯乙烯共聚物和另一个聚合物所得的高抗冲混合物,例如,由聚丙烯酸酯,二烯聚合物或乙烯/丙烯/二烯三元共聚物;和苯乙烯的嵌段共聚物,例如,苯乙烯/丁二烯/苯乙烯,苯乙烯/异戊二烯/苯乙烯,苯乙烯/乙烯/丁烯/苯乙烯或苯乙烯/乙烯/丙烯苯乙烯。
苯乙烯聚合物可能额外地或替代地包括苯乙烯或甲基苯乙烯的接枝共聚物例如,苯乙烯接枝聚丁二烯,苯乙烯接枝聚丁二烯苯乙烯或聚丁二烯丙烯腈;苯乙烯和丙烯腈(或甲基丙烯腈)接枝聚丁二烯和它们的共聚物;苯乙烯和马来酐或顺丁烯二酰亚胺接枝聚丁二烯;苯乙烯,丙烯腈和马来酐或顺丁烯二酰亚胺接枝聚丁二烯;苯乙烯,丙烯腈和甲基丙烯酸甲酯接枝聚丁二烯,苯乙烯和烷基丙烯酸酯或异丁烯酸接枝聚丁二烯,苯乙烯和丙烯腈接枝乙烯-丙烯-二烯三元共聚物,苯乙烯和丙烯腈接枝聚丙烯酸酯或聚甲基丙烯酸酯,苯乙烯和丙烯腈接枝丙烯酸酯/丁二烯共聚物,和上述苯乙烯共聚物之间的混合物。
腈聚合物也适用于本发明的聚合物组合物中的。这些腈聚合物包括丙烯腈和它的类似物的均聚物和共聚物,比如聚甲基丙烯腈,聚丙烯腈,丙烯腈/丁二烯聚合物,丙烯腈/烷基丙烯酸酯聚合物,丙烯腈/烷基异丁烯酸酯/丁二烯聚合物,和上述提到的苯乙烯的不同ABS组合物。
基于丙烯酸的聚合物,比如丙烯酸,甲基丙烯酸,甲基甲基丙烯酸和甲基丙烯酸和它们的酯也是可使用的。这些聚合物包括聚甲基丙烯酸甲酯,和ABS类型的接枝共聚物,其全部或部分的丙烯腈类型单体已经被丙烯酸酯或丙烯酸酰胺所替代。包括其他丙烯酸类型的单体,比如丙烯醛,异丁烯醛,丙烯酰胺和甲基丙烯酰胺的聚合物也可以使用。
含卤素的聚合物也是可用的。这些含卤素聚合物包括树脂,如聚氯丁烯,表氯醇的均-和共-聚物,聚氯乙烯,聚溴乙烯,聚氟乙烯,聚偏二氯乙烯,氯化聚乙烯,氯化聚丙烯,氟化聚乙二烯,溴化聚乙烯,氯化橡胶,氯乙烯-醋酸乙烯共聚物,氯乙烯-乙烯共聚物,氯乙烯-丙烯共聚物,氯乙烯-苯乙烯共聚物,氯乙烯-异丁烯共聚物,氯乙烯-偏氯乙烯共聚物,氯乙烯-苯乙烯-马来酐三元共聚物,氯乙烯-苯乙烯-丙烯腈共聚物,氯乙烯-丁二烯共聚物,氯乙烯-异戊二烯共聚物,氯乙烯-氯化丙烯共聚物,氯乙烯-偏二氯乙烯-醋酸乙烯酯三元共聚物,氯乙烯-丙烯酸酯共聚物,氯乙烯-马来酸酯共聚物,氯乙烯-甲基丙烯酸酯共聚物,氯乙烯-丙烯腈共聚物和内增塑聚氯乙烯。
由本发明亚磷酸酯组合物所稳定的热塑树脂能选择性地额外地包含稳定剂或稳定剂的混合物,其选自由酚类抗氧剂,位阻胺稳定剂,紫外线吸收剂,亚磷酸酯,亚膦酸酯,脂肪酸碱金属盐,水滑石,金属氧化物,环氧大豆油,羟胺,叔胺氧化物,内酯,叔胺氧化物的热反应产物,和硫代增效剂组成的组中。
生成的稳定聚合树脂组合物选择性地还包含不同的传统添加剂,比如下列:
抗氧化剂:抗氧化剂可能包含烷基化单苯酚,例如:2,6-二叔丁基-4-甲酚,2-叔丁基-4,6-二甲苯酚,2,6-二叔丁基-4-乙基苯酚,2,6-二叔丁基-4-正丁基苯酚,2,6二叔丁基-4-异丁基苯酚,2,6-二环戊基-4-甲酚,2-(甲基环己基)-4,6-二甲苯酚,2,6-二十八烷基-4-甲酚,2,4,6-三环己基苯酚,2,6-二叔丁基-4-甲氧基甲基苯酚。烷基化对苯二酚,例如,2,6-二叔丁基-4-甲氧基苯酚,2,5-二叔丁基对苯二酚,2,5-二叔戊基对苯二酚,2,6-联苯-4-十八烷氧基苯酚,也能被用作抗氧化剂。
可用的抗氧化剂还可能包含羟基化的硫代二苯基醚,例如,2,2′-硫代双(6-叔丁基-4-甲酚),2,2′-硫代-双(4-辛基苯酚),4,4′-硫代-双(6-叔丁基-3-甲基苯酚),和4,4′-硫代双(6-叔丁基-2-甲基苯酚)。
亚烷基-双酚也可以用作抗氧化剂,例如,2,2′-亚甲基-双(6-叔丁基-4-甲基苯酚),2,2′-亚甲基-双(6-叔丁基-4-乙基苯酚),2,2′-亚甲基-双(4-甲基-6-(甲基环己基)苯酚),2,2′-亚甲基-双(4-甲基-6-环己基苯酚),2,2′-亚甲基-双(6-壬基-4-甲基苯酚),2,2′-亚甲基-双(6-壬基-4-甲基苯酚),2,2′-亚甲基-双(6-(-甲苯甲基)-4-壬基酚),2,2′亚甲基-双(6-(,-二甲苯甲基)-4-壬基苯酚)。2,2′-亚甲基-双(4,6-二叔丁基苯酚),2,2′-亚乙基-双(6-叔丁基-4-异丁基苯酚),4,4′-亚甲基-双(2,6-二叔丁基苯酚),4,4′-亚甲基-双(6-叔丁基-2-甲基苯酚),1,1-双(5-叔丁基-4-羟-2-甲基苯酚)丁烷,2,6-二(3-叔丁基-5-甲基-2-羟基苯甲基)-4-甲酚,1,1,3-三-(5-叔丁基-4-羟-2-甲基苯基)丁烷,1,1-双(5-叔丁基-4-羟基-2-甲基苯基)-3-十二基-丁硫醇,甘醇-双-(3,3-双-(3′-叔丁基-4′-羟苯基)丁酸酯)-二-(3-叔丁基-4-羟基-5-甲基苯基)-二聚环戊二烯,二-(2-(3′-叔丁基-2′-羟基-5′-甲苯甲基)-6-叔丁基-4-甲基苯基)对酞酸酯,和其他的酚醛塑料,比如单丙烯酸酯的双酚,例如亚乙基-双-2,4-二叔丁基苯酚单丙烯酸酯和3-5二丁基羟苯基丙酸的酯。本文相关的酚类抗氧剂是从下列物质组成的组中选择的:n-十八基-3,5-二叔丁基-4-羟基苯丙酸酯,四[β-(3,5-二叔丁基-4-羟基苯基)丙酸]季戊四醇酯,二-n-十八基-3,5-二叔丁基-4-羟基苯甲基膦酸酯,1,3,5-三(3,5-二叔丁基-4-羟基苯甲基)-异氰脲酸酯,硫代二乙基-双(3,5-二叔丁基-4-羟基苯丙酸酯),1,3,5-三甲基-2,4,6-三(3,5-二叔丁基-4-羟基苯甲基)苯,3,6-二氧杂亚辛基双(3-甲基-5-叔丁基-4-羟基苯丙酸酯),2,6-二叔丁基-对甲酚,2,2′-亚乙基-双(4,6-二叔丁基苯酚),1,3,5-三(2,6-二甲基-4-叔丁基-3-羟基苯甲基)异氰脲酸酯,1,1,3-三(2-甲基-4-羟-5-叔丁基苯基)丁烷,1,3,5-三[2-(3,5-二叔丁基-4-羟基苯丙酰氧基)乙基]异氰脲酸酯,3,5-二-(3,5-二叔丁基-4-羟基苯甲基)莱酚,六甲撑双(3,5-二叔丁基-4-羟基苯丙酸酯),1-(3,5-二叔丁基-4-羟基苯胺基-3,5-二(辛基硫)-s-三嗪,N,N′-六甲撑国际(3,5-二叔丁基-4-羟基苯丙酰胺),双(乙基-3,5-二叔丁基-4-羟基苯甲基膦酸)钙,乙烯-双[3,3-二(3-叔丁基-4-羟苯基)丁酸酯],辛基3,5-二叔丁基-4-羟基苯甲基巯基乙酸酯,双(3,5-二叔丁基-4-羟基苯丙酰基)酰肼,和N,N′-双-[2-(3,5-二叔丁基-4-羟基苯丙酰氧基)乙基]-草酰胺。
其他可用的抗氧化剂包括苄基化合物,例如,1,3,5-三-(3,5-二-叔丁基-4-羟基苯甲基)-2,4,6-三甲苯,双-(3,5-二叔丁基-4-羟基苯甲基)-硫化物,异辛基-3,5-二叔丁基-4-羟基苯甲基巯基乙酸酯,双-(4-叔丁基-3-羟-2,6-二甲苯甲基)二巯基化物-对苯二甲酸酯,1,3,5-三-(3,5-二叔丁基-4,10-羟基苯甲基)异氰脲酸酯,1,3,5-三-(4-叔丁基-3-羟-2,6-二甲苯甲基)异氰脲酸酯,双十八烷基-3,5-二叔丁基-4-羟基苯甲基膦酸酯,四氯邻苯3,5-二叔丁基-4-羟基苯甲基膦酸钙,和1,3,5-三-(3,5-二环己基-4-羟基苯甲基)异氰脲酸酯。
酰基氨基苯酚可用作抗氧化剂,例如,4-羟基-十二烷酸酰基苯胺,4-羟基-硬脂酸酰基苯胺,2,4-双-辛基巯基-6-(3,5-叔丁基-4-羟基苯胺基)-s-三嗪,和辛基-N-(3,5-二叔丁基-4-羟苯基)氨基甲酸脂。
(5-叔丁基-4-羟-3-甲基苯基)丙酸与一元醇或多元醇例如,甲醇,二甘醇,十八醇,三甘醇,1,6-己二醇,季戊四醇,新戊二醇,三-羟乙基异氰脲酸酯,硫二甘醇,和二羟基乙基草酸二酰胺的酯也用作抗氧化剂。
抗氧化剂也可能包含(3,5-二叔丁基-4-间苯二酚)丙酸的酰胺,例如,N,N′-二(3,5-二叔丁基-4-羟基苯基丙酰)己二胺,N,N′-二(3,5-二叔丁基-4-羟基苯基丙酰)三甲撑二胺,和N,N′-二(3,5-二叔丁基-4-羟基苯基丙酰)肼。
实施例
实施例1-合成4-氧代-1,3-二氧杂-2-磷杂萘
向250毫升装有测温传感器,加料漏斗,搅拌器和氮进口的Ace烧瓶中加入22.5g(90mmoles)的4-辛基水杨酸和溶解于50毫升干甲苯的18.2g(80mmoles)干三乙胺。在氮气保护和搅拌下,釜温度保持在-5℃到0℃的同时,向混合物中滴加12.3g(90mmoles)PCl3溶于50mL干甲苯的PCl3溶液。90分后PCl3加入完全。再继续搅拌15分。向反应混合物,主要包含2-氯-4-氧-1,3-二氧杂2-磷杂萘中间体,中滴加11.7g(90mmoles)异辛醇和9.09g(90mmoles)干三乙胺溶于30毫升干甲苯的干三乙胺溶液,滴加持续一小时。在滴加期间,釜温度保持在-5℃到0℃的范围内。滴加完成后,除去冷却,在搅拌下,釜温度恢复到室温。搅拌再继续1小时。利用吸滤滤出盐酸三乙胺沉淀物。滤液放在冰箱中储备过夜。次日清晨过滤掉任何在甲苯溶液中形成的额外的沉淀物。剩余滤液再在真空中蒸干得到78.5g的浅黄粘性液体。31P-NMR分析显示在125ppm处有4-氧代-1,3-二氧杂-2-磷杂萘产物的特征信号。
实施例2
润滑组合物是通过Exxon 100LP基础原料与0.05wt%的Irgamet39,0.03wt%的K-Corr 100A2和0.005wt%的MS-575消泡剂相混合制得。
实施例3
向实施例2的组合物中加入1.0wt%实施例1的取代亚磷酸酯。
实施例4-胺类/酚类的共混物
向实施例2的组合物中加入0.5wt%的Naugalube 438L(单,二,和三-壬基二苯胺的复合混合物)和0.5wt%的Naugalube 531(辛基3-[3,5-二(叔丁基)-4-羟基苯基]丙酸酯)。
实施例5
向实施例2的组合物中加入0.5wt%的Naugalube 438L和0.5wt%实施例1的取代亚磷酸酯。
实施例6
向实施例2的组合物中加入0.5wt%的Naugalube 531和0.5wt%实施例1的取代亚磷酸酯。
实施例7
向实施例2的组合物中加入0.33wt%的Naugalube 438L,0.33wt%的Naugalube 531和0.33wt%实施例1的取代亚磷酸酯。
对比实施例A-L
下列对比实施例是按照U.S.系列No.11/128,929制备的。对比物A包含实施例2的组合物,0.5wt%的Naugalube 438L和0.5wt%的Weston TPP,亚磷酸三苯酯。对比物B包含实施例2的组合物,0.5wt%的Naugalube 438L和0.5wt%的Weston TDP,三异癸基亚磷酸酯。对比物C包含实施例2的组合物,0.5wt%的Naugalube 438L和0.5wt%的Weston 600,二异癸基季戊四醇二亚磷酸酯。对比物D包含实施例2的组合物,0.5wt%的Naugalube 438L和0.5wt%二月桂基亚磷酸酯。对比物E包含实施例2的组合物,0.5wt%的Naugalube 531和0.5wt%的Weston TPP。对比物F包含实施例2的组合物,0.5wt%的Naugalube 531和0.5wt%的Weston TDP。对比物G包含实施例2的组合物,0.5wt%的Naugalube 531和0.5wt%的Weston 600。对比物H包含实施例2的组合物,0.5wt%的Naugalube 531和0.5wt%二月桂基亚磷酸酯。对比物I包含实施例2的组合物,0.33wt%的Naugalube 438L和0.33wt%的Naugalube 531和0.33wt%的WestonTPP。对比物J包含实施例2的组合物,0.33wt%的Naugalube 438L,0.33wt%的Naugalube 531和0.33wt%的Weston TDP。对比物K包含实施例2的组合物,0.33wt%的Naugalube 438L,0.33wt%的Naugalube 531和0.33wt%的Weston 600。对比物L包含实施例2的组合物,0.33wt%的Naugalube 438L,0.33wt%的Naugalube 531和0.33wt%二月桂基亚磷酸酯。
PDSC测试和结果
实施例2-6和对比实施例A-L中的每一个组合物进行PDSC测试,测试条件如表3所示的加压差示扫描量热计(PDSC)条件。表4中的PDSC数据代表各种共混物的氧化诱导时间(OIT)的量度。所用的PDSC仪器是Mettler-Toledo,Inc.制造的Mettler DSC27HP。PDSC方法中会使用钢壳电解槽,且每次实验都是在恒定的氧气压力下进行的。对于200分钟的OIT,仪器在95%可信度条件下,具有±5.0分钟的典型可重复性。全部的试验配方在氮保护下混合15分钟。在PDSC试验之前,每50克制备的试验混合物中加入40μL的油溶性的三价铁的环烷酸盐(在矿物油中占6重量百分数),从而促进50ppm的铁溶于油(iron in oil)。在PDSC试验开始时,PDSC钢壳电解槽利用氧气加压并且按40℃每分钟的加热速度加热到结果表中所列的等温温度。诱导时间是从样品到达它的等温温度时开始直到可以观察到热函变化时的时间长度。氧化诱导时间越长,油的氧化稳定性越好。各个数据点都是对单个试验共混物的两次测试的平均值。
本发明润滑剂抗氧化剂的优势和重要特色展示于其用在工业的″R&O″涡轮机油配方中时。表4所示的结果,其中时间越长代表越稳定的组合物。除非特殊说明,表4中的数值单位为wt%。
A*是Naugalube 438L
B**是Naugalube 531
表4中所示的测试结果表明包含1.0wt%本发明取代亚磷酸酯的实施例3,在PDSC试验中,相对于已知的胺抗氧化剂(1.0wt%的Naugalube 438L=6.3min.@185℃),酚类抗氧剂(1.0wt%的Naugalube 531=2.8min.@185℃),或它们的混合物(实施例4),表现出出众的抗氧化性。
另外,表4中所示的测试结果表明了本发明的取代亚磷酸酯和主抗氧化剂混合所带来的抗氧化剂协同作用。对比期望值,这种协同效应在实施例5-7的PDSC测试中尤其明显。实施例5表明协同效应要好于其他的已知的亚磷酸酯(对比实施例A-D)。实施例6表明协同效应要好于其他已知的亚磷酸酯(对比实施例E-H)。实施例7表明协同效应相当于或好于其他的已知亚磷酸酯(对比实施例I-L)。另外实施例5-7每一个都要强于实施例4中所示的胺和酚类抗氧剂共混物。
鉴于许多变化和修改可以在不离开本发明基础原则的情况下产生,因此应参考附加权利要求书来理解赋予本发明的保护范围。
在此描述的所有专利,文章和其它材料的公开内容由此全文引入本说明书作为参考。描述为“包含”多种定义的组分的组合物解释为包括通过掺混定义的多种组分而形成的组合物。本发明的原理,优选实施方案,和操作模式已经在说明书前述部分中描述。申请人提交的是他们的发明,但是,发明不应被理解为仅限于特定公开的实施方案,这些公开实施方案应被认定是说明性的而非限制性的。本领域的技术人员变化可以在不离开本发明基础原则的情况下对发明进行变化。
Claims (20)
2.权利要求1的化合物,其中R1和R4独立地选自2-乙基-己基、正辛基、和异辛基。
3.权利要求1的化合物,其中R1选自C4-C10烷基。
7.权利要求6的方法,其中β羟基酸是水杨酸。
9.权利要求8的方法,进一步包括加入至少一种主抗氧化剂来形成添加剂共混物。
11.权利要求9的组合物,其中至少一种主抗氧化剂含有下列通式代表的二芳基仲胺化合物:
(R8)a-Ar1-NH-Ar2-(R9)b
其中Ar1和Ar2独立地是芳族烃基,R8和R9独立地是氢或具有6到大约100个碳原子的烃基,和a和b独立地是0到3但是(a+b)不大于4。
12.权利要求11的组合物,其中二芳基仲胺化合物包括选自单取代、二取代或三取代二苯胺的二苯胺。
16.权利要求9的组合物,其中润滑基础原料选自汽轮机润滑剂、蒸汽-燃气轮机润滑剂、自动传动液、齿轮润滑剂、压缩机润滑剂、金属加工润滑剂、液压油、及聚α烯烃。
18.权利要求17的组合物,其中热塑性弹性体选自聚乙烯、聚丙烯、聚丙烯、聚异丁烯、聚丁烯-1、聚甲基戊烯-1、聚异戊二烯和聚丁二烯。
19.权利要求17的组合物,进一步包含下列通式代表的取代酚:
其中R10,R11和R12独立地是氢或具有1到100个碳原子的烃基,条件是至少一个邻位基团包含支化烷基链。
20.权利要求17的组合物,进一步包含下列通式代表的二芳基仲胺化合物:
(R8)a-Ar1-NH-Ar2-(R9)b
其中Ar1和Ar2独立地是芳族烃基,R8和R9独立地是氢或具有6到大约100个碳原子的烃基,和a和b独立地是0到3但是(a+b)不大于4。
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103725372A (zh) * | 2012-10-15 | 2014-04-16 | 中国石油化工股份有限公司 | 内燃机润滑油组合物 |
CN103725353A (zh) * | 2012-10-15 | 2014-04-16 | 中国石油化工股份有限公司 | 一种低碱值润滑油添加剂、其制备方法及润滑油组合物 |
CN103725357A (zh) * | 2012-10-15 | 2014-04-16 | 中国石油化工股份有限公司 | 一种低碱值清净剂、其制备方法及润滑油组合物 |
CN110621950A (zh) * | 2017-05-22 | 2019-12-27 | 伊莱克斯家用电器股份公司 | 具有至少一个内部塑料内衬的制冷器具及制造内衬的方法 |
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Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012066575A1 (en) * | 2010-11-19 | 2012-05-24 | Indian Oil Corporation Ltd. | A high performance gearbox lubricant with enhanced drain interval for heavy duty commercial vehicles and a process for producing the same |
CN103031188A (zh) * | 2011-10-09 | 2013-04-10 | 中国石油化工股份有限公司 | 螺杆式氨压缩机油组合物 |
JP5542289B2 (ja) * | 2012-01-23 | 2014-07-09 | トヨタ自動車株式会社 | オイル添加物およびオイルフィルター |
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GB2551983B (en) * | 2016-06-30 | 2020-03-04 | Sophos Ltd | Perimeter encryption |
KR102107930B1 (ko) | 2019-02-28 | 2020-05-08 | 대림산업 주식회사 | 유압 작동유용 윤활유 조성물 |
JP7444644B2 (ja) * | 2020-03-06 | 2024-03-06 | 出光興産株式会社 | 潤滑油組成物、及び潤滑油組成物の使用方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0625493A (ja) * | 1992-04-27 | 1994-02-01 | Akishima Kagaku Kogyo Kk | 熱安定化された塩素含有樹脂組成物 |
JP2000038487A (ja) * | 1998-07-22 | 2000-02-08 | Akishima Kagaku Kogyo Kk | 環境ホルモン物質を含有しない食品包装フィルム用塩化ビニル系樹脂組成物 |
US20070105992A1 (en) * | 2005-11-07 | 2007-05-10 | Hayder Zahalka | Cycloalkyl phosphites as stabilizers for thermoplastic resins |
Family Cites Families (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2612488A (en) * | 1950-11-02 | 1952-09-30 | Standard Oil Dev Co | Stabilization of organic materials with aryl polyphosphites |
BE557947A (zh) * | 1956-05-31 | |||
US3556999A (en) * | 1965-06-03 | 1971-01-19 | Rohm & Haas | Stabilized fluids |
US3652411A (en) * | 1969-12-04 | 1972-03-28 | Mobil Oil Corp | Polyglycol base lubricant |
JPS572757B2 (zh) * | 1973-06-13 | 1982-01-18 | ||
US3923672A (en) * | 1974-10-07 | 1975-12-02 | Continental Oil Co | Turbine oil compositions |
SU1033497A1 (ru) * | 1982-04-29 | 1983-08-07 | Омский государственный университет | Способ получени 2-(2-хлоралкокси)-2-оксо-1,4,2-диоксафосфепанов |
CA1248516A (en) * | 1985-07-15 | 1989-01-10 | Stephen C. Cohen | Lubricating oil compositions containing novel combination of stabilizers |
US4832867A (en) | 1987-10-22 | 1989-05-23 | Idemitsu Kosan Co., Ltd. | Lubricating oil composition |
US5232614A (en) * | 1989-02-23 | 1993-08-03 | Exxon Chemical Patents Inc. | Lubricating oil compositions and additives for use therein |
CA2025416C (en) * | 1990-09-14 | 1999-06-22 | Stephen Cedric Cohen | Lubricating oil compositions containing novel combination of stabilizers (no. 2) |
US5688847A (en) * | 1996-11-07 | 1997-11-18 | Witco Corporation | Polycyclic fluorophosphites useful as stabilizers |
US6172014B1 (en) * | 1998-06-30 | 2001-01-09 | Pennzoil-Quaker State | Method of lubricating compression cylinders used in the manufacture of high-pressure polyethylene |
US6326336B1 (en) * | 1998-10-16 | 2001-12-04 | Ethyl Corporation | Turbine oils with excellent high temperature oxidative stability |
GB0011189D0 (en) * | 2000-05-10 | 2000-06-28 | Great Lakes Chemical Europ | Anti-oxidant additives |
DE10140086A1 (de) * | 2001-08-16 | 2003-02-27 | Oxeno Olefinchemie Gmbh | Neue Phosphitverbindungen und neue Phosphitmetallkomplexe |
DE10360772A1 (de) * | 2003-12-23 | 2005-07-28 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von Organoacylphosphiten |
US7799101B2 (en) * | 2004-09-29 | 2010-09-21 | Chemtura Corporation | Stabilized lubricant compositions |
US7442732B2 (en) * | 2005-03-29 | 2008-10-28 | Crompton Corporation | Hindered amine light stabilizers comprising neoalkanediol phosphites |
US20070142237A1 (en) * | 2005-11-09 | 2007-06-21 | Degonia David J | Lubricant composition |
US8313885B2 (en) * | 2005-11-10 | 2012-11-20 | Agfa Graphics Nv | Lithographic printing plate precursor comprising bi-functional compounds |
JP5258162B2 (ja) * | 2005-12-09 | 2013-08-07 | 出光興産株式会社 | 潤滑油組成物 |
US7888414B2 (en) | 2006-06-20 | 2011-02-15 | Chemtura Corporation | Liquid phosphite blends as stabilizers |
-
2008
- 2008-06-27 US US12/163,557 patent/US8049041B2/en not_active Expired - Fee Related
-
2009
- 2009-05-18 KR KR1020107027741A patent/KR20110037952A/ko not_active Application Discontinuation
- 2009-05-18 RU RU2011102929/04A patent/RU2500683C2/ru not_active IP Right Cessation
- 2009-05-18 JP JP2011514657A patent/JP5341989B2/ja not_active Expired - Fee Related
- 2009-05-18 WO PCT/US2009/044330 patent/WO2009158078A1/en active Application Filing
- 2009-05-18 CN CN2009801217817A patent/CN102066391A/zh active Pending
- 2009-05-18 EP EP09770613.9A patent/EP2294074B1/en not_active Not-in-force
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0625493A (ja) * | 1992-04-27 | 1994-02-01 | Akishima Kagaku Kogyo Kk | 熱安定化された塩素含有樹脂組成物 |
JP2000038487A (ja) * | 1998-07-22 | 2000-02-08 | Akishima Kagaku Kogyo Kk | 環境ホルモン物質を含有しない食品包装フィルム用塩化ビニル系樹脂組成物 |
US20070105992A1 (en) * | 2005-11-07 | 2007-05-10 | Hayder Zahalka | Cycloalkyl phosphites as stabilizers for thermoplastic resins |
Non-Patent Citations (4)
Title |
---|
J.A.CADE ET AL.: ""Reaction between phosphorus trichloride and salicylic acid"", 《CHEMISTRY AND INDUSTRY》 * |
L. M. BURNAEVAA,ET AL.: ""1,3,2(1,4,2)-Dioxaphosphepins Annelated with Naphthalene Fragment: Synthesis and Steric Structure"", 《RUSSIAN JOURNAL OF GENERAL CHEMISTRY》 * |
V. F. MIRONOV ET AL.: ""Reaction of 2-methoxy-1,3,2-dioxa-phosphorino[4,5-b]pyridin-4(4H)-one with hexafluoroacetone"", 《RUSSIAN CHEMICAL BULLETIN, INTERNATIONAL EDITION》 * |
V. F. MIRONOV,ET AL.: ""Dialkyl Arylcarbonylphosphonates in the Reactions with 2-RO-4-0xo-5,6-benzo-1,3,2-dioxaphosphorinan Steric Structure of the Derivatives of 4-Aryl-2-hydroxy-4-dialkox~phosphoryl-5-oxo=6,7-benzo- 1,3,2-dioxaphosphepine 2-Oxides"", 《RUSSIAN JOURNAL OF GENERAL CHEMISTRY》 * |
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CN110621950A (zh) * | 2017-05-22 | 2019-12-27 | 伊莱克斯家用电器股份公司 | 具有至少一个内部塑料内衬的制冷器具及制造内衬的方法 |
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