CN1041610A - 润滑油组合物 - Google Patents

润滑油组合物 Download PDF

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Publication number
CN1041610A
CN1041610A CN89104887A CN89104887A CN1041610A CN 1041610 A CN1041610 A CN 1041610A CN 89104887 A CN89104887 A CN 89104887A CN 89104887 A CN89104887 A CN 89104887A CN 1041610 A CN1041610 A CN 1041610A
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alkyl
phenyl
group
composition
compound
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CN89104887A
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CN1020748C (zh
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劳尔夫·苏迈切
沙姆埃尔·埃万斯
鲍尔·达伯恩
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Novartis AG
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Ciba Geigy Corp
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Abstract

一种对抗氧化降解作用稳定的、以矿物油或合成油为基础的润滑油，稳定是通过加入一种混合物来实现的，该混合物含有至少一种通式I或II的特殊芳香胺和至少一种位阻胺。该润滑油可以含有其他抗氧化剂或添加剂，该润滑油最好用作车用机油。

Description

本发明涉及一种抗氧化降解作用稳定的润滑油组合物。该稳定是通过加入至少两种特殊添加剂而达到的。
众所周知，一般习惯于向矿物油或合成油润滑油中加入添加剂，以提高其使用性能。润滑油用抗氧化降解添加剂。即所谓的抗氧化剂是特别重要的。氧化降解起非常重要的作用。特别是在 机油中更是如此，这是因为发动机的燃烧室的温度是很高的，且除氧气外，还有存在有起氧化催化剂作用的氮的氧化物（NOx）。
芳香胺，如烷基化二苯基胺或烷基化吩噻嗪，特别可以用作润滑油用抗氧化剂。例如Ep-A-149，422或GB-A-1，090，688公开了这类胺。这类胺与其他抗氧化剂，如亚磷酸三芳基酯、硫代二丙酸酯或酸型抗氧化剂，一起配合使用也是公知的，例如Ep-A-49，133所述。
我们发现芳香胺与位阻胺的组合物是一种非常适宜的润滑油用抗氧化剂。
本发明提供了一种润滑油组合物，其中包括：
（A）一种矿物或合成基础油或这些油的混合物;
（B）至少一种通式Ⅰ或Ⅱ的芳香胺。
其中，R1是C1-18烷基、C7-9苯烷基、C5-12环烷基、苯基、C7-8烷苯基、C7-18烷氧苯基或萘基。R2是苯基、C7-18烷基苯基、C7-18烷氧基苯基或萘基，R3是氢、C1-12烷基、苄基、烯丙基、甲基烯丙基、苯基或基团-CH2SR4。R4是C4-18烷基、-CH2COO（C4-18烷基）或-CH2CH2COO（C4-18烷基），R5和R6各自为H、C1-18烷基或C7-9苯基烷基;和
（C）至少一种位阻胺。
如R3为C1-12烷基，它可为直链或支链烷基，例如甲基、乙基、丙基、丁基、戊基、己基、辛基、壬基、癸基或十二烷基。作为C1-18烷基，R1、R5和R6另外还可以为十四烷基、十五烷基、十六烷基或者十八烷基。作为C4-18烷基。R4也可以为例如正丁基、叔丁基、正己基、叔辛基、正十二烷基或十八烷基。
作为C7-9苯烷基，R1、R5和R6可为为。例如，苄基、2-苯基乙基、α-甲基苄基、2-苯基丙基、或α，α-二甲基苄基。
作为C7-18烷基苯基，R1和R2可以为直链或支链烷基。其例子为甲苯基、乙基苯基、异丙基苯基、叔丁基苯基、仲戊基苯基正己基苯基、叔辛基苯基、异壬基苯基或正十二烷基苯基。R1和R2也可以为烷基苯基的混合基，例如那些在工业中用烯烃进行二苯基胺的烷基化所生产的基团。烷基最好是在芳胺的对位。
作为组分（B），最好使用通式Ⅰ或Ⅱ的化合物，其中R1是C1-4烷基、C7-9苯基烷基、环己基、苯基、C10-18烷基苯基或萘基。R2是C10-18烷基苯基或苯基，R3是H、C1-8烷基、苄基、烯丙基或基团-CH3SR4，R4是C8-18烷基或-CH2COO（C8-18烷基），R5和R6各自为C1-12烷基或C7-9苯基烷基。
在通式Ⅰ的化合物中，特别好的是其中R1和R2各自为苯基或C10-18烷基苯基、R3为H的。
在通式Ⅱ的化合物中，特别好的是，其中R3为H、R5和R6各自为H或C4-12烷基的。
通式Ⅰ化合物的例子是：
二苯胺
N-烯丙基二苯胺
4-异丙氧基二苯胺
N-苯基-1-萘基胺
N-苯基-2-萘基胺
二-4-甲氧基苯基胺
二-〔4-（1，3-二甲基丁基）苯基〕胺
二-〔4-（1，1，3，3-四甲基丁基）苯基〕胺
叔辛基化N-苯基-1-萘基胺
二苯基胺与二异丁烯反应生成的工业混合物
（单一，双一和三烷基化的叔丁基和叔辛基二苯胺）
吩噻嗪
N-烯丙基吩噻嗪
3，7-二叔辛基吩噻嗪
吩噻嗪与二异丁烯反应得到的工业混合物
特别好的组分（B）是4，4′-二叔丁基二苯基胺或3，7-二叔辛基吩噻嗪或二苯胺与二异丁烯反应生成的工业混合物，特别是含有下列组分的混合物：
a）不大于5%（重量）的二苯胺，
b）8-15%（重量）的4-叔丁基二苯胺，
c）24～32%（重量）的4-叔丁基二苯胺，4，4′-二叔丁基二苯胺和2，4，4′-三叔辛基二苯胺，
d）23～34%（重量）的4-叔丁基-4′-叔辛基二苯胺，2，2′-和3，3′-二-叔辛基二苯胺和2，4-二叔丁基-4′-叔辛基二苯胺，
e）21～34%（重量）的4，4′-二叔辛基二苯胺和2，4-二叔辛基-4′-叔丁基二苯胺。
组分（c）可以是环或非环位阻胺。
较好的组分（c）是含有至少一个通式Ⅲ表示的基团的化合物。
Figure 891048871_IMG8
其中，R是H或甲基，最好是H。该化合物为聚烷基哌啶的衍生物，特别是2，2，6，6-四甲基哌啶。这些聚烷基哌啶最好在4位上具有一个或二个极性取代基或一个极性螺环体系。
下述各类聚烷基哌啶特别重要：
a）式（Ⅳ）化合物
Figure 891048871_IMG9
其中n为整数1-4;最好为1或2;R是H或甲基。R11为氢、烃氧基、羟基、C1-C12烷基、C3-C8链烯基、C3-C8链炔基、C7-C12芳烷基、C1-C18烷氧基、C5-18环烷氧基、C7-9苯基烷氧基、C1-C8烷酰基、C3-C5链烯酰基、C1-18烷酰氧基、苄 氧基、缩水甘油基或-CH2CH（OH）-Z基团（其中Z为氢、甲基或苯基），R11最好为C1-C4烷基、烯丙基、苄基、乙酰基或丙烯酰基;如果n为1，则R12为氢、中间有（或没有）一个或多个氧原子的C1-C18烷基、氰乙基、苄基、缩水甘油基、脂族、脂环族、芳脂族、不饱和的或芳香族羧酸、氨基甲酸或含磷酸的一价基团、或一价甲硅烷基，最好为具有2-18个碳原子的脂族羧酸基团、具有7-15个碳原子的脂环族羧酸基团、具有3-5个碳原子的α，β-不饱和羧酸基团或具有7-15个碳原子的芳族羧酸;如果n为2，则R12为C1-C12亚烷基、C4-C12亚烯基、亚二甲苯基、脂族、脂环族、芳脂族或芳香族二羧酸、二（氨基甲酸）或含磷酸的二价基团、或为二价甲硅烷基，最好为具有2-36个碳原子的脂族二羧酸基团、具有8-14个碳原子的脂环族或芳香族二羧酸基团、或为具有8-14个碳原子的脂族、脂环族或芳香族二（氨基甲酸）;如果n为3，则R12为脂族、脂环族或芳香族三羧酸的三价基团、芳香族三（氨基甲酸）或含磷酸的三价基团、或为三价甲硅烷基;如果n为4，则R12为脂族、脂环族或芳香族四羧酸的四价基团。
如果任何取代基为C1-C12烷基，其实例可为甲基、乙基、正丙基、正丁基、仲丁基、叔丁基、正己基、正辛基、2-乙基己基正壬基、正癸基、正十二烷基或正十二烷基。
如果R11或R12为C1-C18烷基，可为上述基团，还可为如正十三烷基、正十四烷基、正十六烷基或正十八烷基。
如R11为C3-C8链烯基，其实例为1-丙烯基、烯丙基、甲代烯丙基、2-丁烯基、2-戊烯基、2-己烯基、2-辛烯基和4-叔丁基-2-丁烯基。
R11为C3-C8链炔基时最好为炔丙基。
R11为C7-C12芳烷基时最好为苯乙基，特别是苄基。
R11为C1-C8烷酰基时，其实例为甲酰基、丙酰基、丁酰基和辛酰基，但最好为乙酰基;R11为C3-C5链烯酰基时，RR11最好为丙烯酰基。
R12为羧酸的一价基团时，其实例为乙酸、己酸、硬脂酸、丙烯酸、异丁烯酸、苯甲酸或β-（3，5-二-叔丁基-4-羟苯基基）-丙酸的一价基团。
R12为二羧酸的二价基团时，其实例为丙二酸、丁二酸、戊二酸、己二酸、辛二酸、癸二酸、顺丁烯二酸、苯二甲酸、二丁基丙二酸、二苄基丙二酸、丁基-（3，5-二叔丁基-4-羟苄基）-丙二酸或双环庚烯二甲酸的二价基团。
R12为三羧酸的三价基团时，其实例为1，2，4-苯三酸或次氮基三乙酸的三价基团。
R12为四羧酸的四价基团时，其实例为丁烷-1，2，3，4-四甲酸或1，2，4，5-苯四酸基团。
R12为二（氨基甲酸）的二价基团时，其实例为亚己基二（氨基甲酸）或2，4-甲代亚苯基二（氨基甲酸）的二价基团。
最好的通式Ⅳ的化合物是这些化合物，即其中R是H，R11是H或甲基，n是2，R12是具有4～12个碳的脂族二羧酸的二酰基。
下述化合物为该类多烷基哌啶化合物的实例：
1）4-羟基-2，2，6，6-四甲基哌啶，
2）1-烯丙基-4-羟基-2，2，6，6-四甲基哌啶，
3）1-苄基-4-羟基-2，2，6，6-四甲基哌啶，
4）1-（4-叔丁基-2-丁烯基）-4-羟基-2，2，6，6-四甲基哌啶，
5）4-硬脂酰氧基-2，2，6，6-四甲基哌啶，
6）1-乙基-4-水杨酰氧基-2，2，6，6-四甲基哌啶啶，
7）4-异丁烯酰氧基-2，2，6，6-五甲基哌啶，
8）1，2，2，6，6-五甲基哌啶-4-基-β-（3，5-二叔丁基-4-羟苯基）-丙酸酯。
9）二（1-苄基-2，2，6，6-四甲基哌啶-4-基）马来酸酯，
10）二（2，2，6，6-四甲基哌啶-4-基）丁二酸酯，
11）二（2，2，6，6-四甲基哌啶-4-基）戊二酸酯，
12）二（2，2，6，6-四甲基哌啶-4-基）己二酸酯，
13）二（2，2，6，6-四甲基哌啶-4-基）癸二酸酯，
14）二（1，2，2，6，6-五甲基哌啶-4-基）癸二酸酯，
15）二（1，2，3，6-四甲基-2，6-二乙基-哌啶-4-基）癸二酸酯，
16）二（1-烯丙基-2，2，6，6-四甲基哌啶-4-基基）邻苯二甲酸酯，
17）1-羟基-4-β-氰基乙氧基-2，2，6，6-四甲基哌啶，
18）1-乙酰基-2，2，6，6-四甲基哌啶-4-基乙酸酯，
19）三（2，2，6，6-四甲基哌啶-4-基）偏苯三酸酯，
20）1-丙烯酰-4-苄氧基-2，2，6，6-四甲基哌啶，
21）二（2，2，6，6-四甲基哌啶-4-基）二乙基-丙二酸酯，
22）二（1，2，2，6，6-五甲基哌啶-4-基）二丁基-丙二酸酯，
23）二（1，2，2，6，6-五甲基啶-4-基）丁基-（3，5-二叔丁基-4-羟苄基）-丙二酸酯，
24）二（1-辛氧基-2，2，6，6-四甲基哌啶-4-基）癸二酸酯，
25）二（1-环己氧基2，2，6，6-四甲基哌啶-4-基）癸二酸酯，
26）己烷-1′，6′-双（4-氨基甲酰氧基-1-正丁基-2，2，6，6-四甲基哌啶），
27）甲苯-2′，4′-双（4-氨基甲酰氧基-1-正丙基-2，2，6，6-四甲基哌啶），
28）二甲基-双（2，2，6，6-四甲基哌啶-4-氧基）-硅烷，
29）苯基-三（2，2，6，6-四甲基哌啶-4-氧基）-硅烷，
30）三（1-丙基-2，2，6，6-四甲基哌啶-4-基）亚磷酸酯，
31）三（1-丙基-2，2，6，6-四甲基哌啶-4-基）磷酸酯，
32）苯基-双（1，2，2，6，6-五甲基哌啶-4-基）磷酸酯，
33）4-羟基-1，2，2，6，6-五甲基哌啶，
34）4-羟基-N-羟乙基-2，2，6，6-四甲基哌啶，
35）4-羟基-N-（2-羟丙基）-2，2，6，6-四甲基哌啶。
36）1-缩水甘油基-4-羟基-2，2，6，6-四甲基哌啶。
b）式（Ⅴ）化合物
Figure 891048871_IMG10
其中n为整数1或2，R11的含义与a）中定义相同，R13为氢C1-C12烷基、C2-C5羟烷基、C5-C7环烷基、C7-C8芳烷基、C2-C18烷酰基、C3-C5链烯酰基或苯甲酰基或者下列通式的基团：
当n为1时，R14为氢、C1-C18烷基、C3-C8链烯基、C5-C7环烷基、被羟基、氰基、烷氧羰基或脲基取代的C1-C4烷基、缩水甘油基或具有式-CH2-CH（OH）-Z或-CONH-Z（其中Z为氢、甲基或苯基）的基团;如果n为2，R4为C2-C12亚烷基、C6-C12亚芳基、亚二甲苯基、-CH2-CH（OH）-CH2-基或式-CH2-CH（OH）-CH2-O-D-O-基（其中D为C2-C10亚烷基、C6-C15亚芳基或C6-C12亚环烷基），或者，如果R13不是烷酰基、链烯酰基或苯甲酰基，R14还可为脂族、脂环族或芳香族二羧酸或二（氨基甲酸）的二价 基团或基团-CO-;如果n为1，R3和R4可共同代表脂族、脂环族或芳香族1，2-二甲酸或1，3-二甲酸的二价 基团。
如果任何取代基为C1-C12烷基或C1-C18烷基，其含义与a）中定义相同。
如果任何取代基为C5-C7环烷基，最好为环己基。
如果R13为C7-C8芳烷基，最好为苯乙基或特别是苄基。如R13为C2-C5羟烷基，最好为2-羟乙基或2-羟丙基。
如果R13为C2-C18烷酰基，其实例为丙酰基、丁酰基、辛酰基、十二烷酰基、十六烷酰基或十八烷酰基，但最好为乙酰基。如果R13为C3-C5链烯酰基，最好为丙烯酰基。
如果R14为C2-C8链烯基，其实例为烯丙基、甲代烯丙基、2-丁烯基、2-戊烯基、2-己烯基或2-辛烯基。
如果R14为被羟基、氰基、烷氧羰基或脲基取代的C1-C4烷基，其实例为2-羟乙基、2-羟丙基、2-氰乙基、甲氧羰基甲基2-乙氧羰基乙基、2-氨基羰基丙基或2-（二甲基氨基羰基）乙基
如果任何取代基为C2-C12亚烷基，其实例为亚乙基、亚丙基、2，2-二甲基亚丙基、四亚甲基、六亚甲基、八亚甲基、十亚甲基或十二亚甲基。
如果任何取代基为C6-C15亚芳基，其实例为邻-、间-、或对-亚苯基、1，4-亚萘基或4，4′-亚联苯基。
D为C6-C12亚环烷基时，最好为亚环己基。
较好的通式Ⅴ的化合物是这些，即其中n是1或2，R是H，R11是H或甲基，R13是H、C1-12烷基或下列通式的基团
Figure 891048871_IMG12
当n＝1时，R14是H或C1-12烷基;当n＝2时，R14是C2-8亚烷基
下述化合物为该类多烷基哌啶化合物的实例：
37）N，N′-双（2，2，6，6-四甲基哌啶-4-基）-六亚甲基-1，6-二胺，
38）N，N′-双（2，2，6，6-四甲基哌啶-4-基）-六亚甲基-1，6-二乙酰基胺，
39）双（2，2，6，6-四甲基哌啶-4-基）胺，
40）4-苯甲酰基氨基-2，2，6，6-四甲基哌啶，
41）N，N′-双（2，2，6，6-四甲基啶-4-基）-N，N′-二丁基己二酰二胺，
42）N，N′-双（2，2，6，6-四甲基啶-4-基）-N，N′-二环己基-2-羟亚丙基-1，3-二胺，
43）N，N′-双（2，2，6，6-四甲基哌啶-4-基）-对-亚二甲苯基二胺，
44）N，N′-双（2，2，6，6-四甲基哌啶-4-基）-琥珀二酰胺，
45）二（2，2，6，6-四甲基啶-4-基）-N-（2，2，6，6-四甲基哌啶-4-基）-β-氨基二丙酸酯;
46）具有下式的化合物
47）4-（双-2-羟乙基氨基）-1，2，2，6，6-五甲基哌啶。
48）4-（3-甲基-4-羟基-5-叔丁基苯甲酰胺基）-2，2，6，6-四甲基哌啶，
49）4-异丁烯基氨基-1，2，2，6，6-五甲基哌啶。
c）（Ⅳ）化合物
Figure 891048871_IMG14
其中n为整数1或2，R1的含义与a）中的定义相同：如果n为1，R15为C2-C8亚烷基或C2-C8羟基亚烷基或C4-C22酰氧基亚烷基;如果n为2，R15为式（-CH2）2C（CH2-）2基团。
如果R15为C2-C8亚烷基或C2-C8羟基亚烷基，其实例为亚乙基、1-甲基亚乙基、亚丙基、2-乙基亚丙基或2-乙基-2-羟甲基亚丙基。
如果R15为C4-C22酰氧基亚烷基，其实例为2-乙基-2-乙酰氧基甲基亚丙基。
下述化合物为该类多烷基哌啶化合物的实例：
50）9-氮杂-8，8，10，10-四甲基-1，5-二噁螺[5.5]十一烷，
51）9-氮杂-8，8，10，10-四甲基-3-乙基-15-二噁螺[5，5]十一烷，
52）8-氮杂-2，7，7，8，9，9-六甲基-1，4-二噁螺[4，5]癸烷，
53）9-氮杂-3-羟甲基-3-乙基-8，8，9，10，10-五甲基-1，5-二噁螺[5，5]十一烷，
54）9-氮杂3-乙基-3-乙酰氧基甲基-9-乙酰基-8，8，10，10-四甲基-1，5-二噁螺[5，5]十一烷，
55）2，2，6，6-四甲基哌啶-4-螺-2′-（1′，3′-二噁烷）-5′-螺-5″-（1″，3″-二噁烷）-2″-螺-4″′-（2″′，2″′，6″′，6″′-四甲基哌啶）。
d）式（ⅦA）、（ⅦB）和（ⅦC）化合物
Figure 891048871_IMG15
其中n为整数1或2;R和R11的含义与a）中的定义相同：R16为氢、C1-C12烷基、烯丙基、苄基、缩水甘油基或C2-C6烷氧烷基;如果n为1，R17为氢、C1-C12烷基、C3-C5链烯基、C7-C9芳烷基、C5-C7环烷基、C2-C4羟烷基、C2-C6烷氧烷基、C6-C10芳基、缩水甘油基或式-（CH2）p-COO-Q或式-（CH2）p-O-CO-Q（（其中p为1或2，Q为C1-C4烷基或苯基）基团;如果n为2R17为C2-C12亚烷基、C4-C12亚烯基、C6-C12亚芳基、式-CH2-CH（OH）-CH2-O-D-O-CH2-CH（OH）-CH2-（其中D为C2-C10亚烷基、C6-C15亚芳基或C6-C12亚环烷基）基团、或者为-CH2CH（OZ′）CH2-（OCH2-CH（OZ′）CH2）2-（其中Z′为氢、C1-C18烷基、烯丙基、苄基、C2-C12烷酰基或苯甲酰基）基团;T1和T2分别独立地为氢或被卤素或C1-C4烷基取代或未取代的C1-C18烷基或C6-C10芳基或C7-C8芳烷基，或者T1和T2与连接它们的碳原子一起形成C5-C15环烷基。
如果任何取代基为C1-C12烷基，其实例为甲基、乙基、正丙基、正丁基、仲丁基、叔丁基、正己基、正辛基、2-乙基己基、正壬基、正壬基、正十一烷基或正十二烷基或正十二烷基。
如果任何取代基为C1-C18烷基，其实例可为上述基团，以及正十三烷基、正十四烷基、正十六烷基或正十八烷基。
如果任何取代基为C2-C6烷氧烷基，其实例为甲氧甲基、乙氧甲基、丙氧甲基、叔丁氧甲基、乙氧乙基、乙氧丙基、正丁氧乙基、叔丁氧乙基、异丙氧乙基或丙氧丙基。
如果R17为C3-C5链烯基，其实例为1-丙烯基、烯丙基、甲代烯丙基、2-丁烯基或2-戊烯基。
如果R17、T1和T2为C7-C9芳烷基，最好为苯乙基，或特别是苄基。如果T1和T2与碳原子一起形成环烷基，可为环戊基、环己基、环辛基或环十二烷基。
如果R17为C2-C4羟烷基，其实例为2-羟乙基、2-羟丙基、2-羟丁基或4-羟丁基。
如果R17、T1和T2为C6-C10芳基，最好为被卤素或C1-C4烷基取代或未取代的苯基、α-萘基或β-萘基。
R17为C2-C12亚烷基的实例为亚乙基、亚丙基、2，2-二甲基亚丙基、四亚甲基、六亚甲基、八亚甲基、十亚甲基或十二亚甲基。
R17为C4-C12亚烯基时，最好为2-亚丁烯基、2-亚戊烯基或3-亚己烯基。
R17为C6-C12亚芳基的实例为邻-、间-或对-亚苯基、1，4-亚萘基或4，4′-亚联苯基。
Z′为C2-C12烷酰基的实例为丙酰基、丁酰、辛酰基或十二烷酰基，但最好为乙酰基。
D为C2-C10亚烷基、C6-C15亚芳基或C6-C12亚环烷基，其定义与b）中的定义相同。
下述化合物为该类多烷基哌啶化合物的实例：
56）3-苄基-1，3，8-三氮杂-7，7，9，9-四甲基螺[4，5]癸烷-2，4-二酮，
57）3-正辛基-1，3，8-三氮-7，7，9，9-四甲基螺[4，5]癸烷-2，4-二酮，
58）3-烯丙基-1，3，8-三氮杂-1，7，7，9，9-五甲基螺[4，5]癸烷-2，4-二酮，
59）3-缩水甘油基-1，38-三氮杂-7，7，8，9，9-五甲基螺[4，5]癸烷-2，4-二酮，
60）1，3，7，7，8，9，9-七甲基-1，3，8-三氮杂螺[4，5]癸烷-2，4-二酮，
61）2-异丙基-7，7，9，9-四甲基-1-氧杂-3，8-二氮杂-4-氧代螺[4，5]癸烷，
62）2，2-二丁基-7，7，9，9-四甲基-1-氧杂-3，8-二氮杂-4-氧代螺[4，5]癸烷，
63）2，2，4，4，-四甲基-7-氧杂-3，20-二氮杂-21-氧代二螺[5，1，11，2]二十一烷，
64）2-丁基-7，7，9，9-四甲基-1-氧杂-4，8-二氮杂-3-氧代螺[4，5]癸烷，
65）8-乙酰基-3-十二烷酰-1，3，8-三氮杂-7， 7，9，9-四甲基螺[4，5]癸烷-2，4-二酮，
或具有下式的化合物：
Figure 891048871_IMG17
e）式（Ⅷ）化合物
Figure 891048871_IMG18
其中n为整数1或2;R18为具有下式的基团：
其中R11、R的含义与a）中的定义相同，E为-O-或-NR11-，A为C2-C6亚烷基或-（CH2）3-O-且X为整数0或1;R19与R18相同，也可为基团-NR21R22、-OR28、-NHCH2OR23或-N（CH2OR23）2中的一个;如果n为1，R20与R18或R19相同，如果n为2，R20为基团-E-B-E[其中B为中间有或没有-N（R21）的C2-C6亚烷基];R11为C1-C12烷基、环己基、苄基或C1-C4羟烷基或为具有下式的基团：
R12为C1-C12烷基、环己基、苄基或C1-C4羟烷基，R13为氢、C1-C12烷基或苯基，或者R11与R12共同代表C4-C5亚烷基或C4-C5氧杂亚烷基，如
Figure 891048871_IMG21
的基团，或者R21与R22均为基团：
如果任何取代基为C1-C12烷基，其实例为甲基、乙基、正丙基、正丁基、仲丁基、叔丁基、正己基、正辛基、2-乙基己基、正壬基、正癸基、正十一烷基或正十二烷基。
如果任何取代基为C1-C4羟烷基，其实例为2-羟乙基、2-羟丙基、3-羟丙基、2-羟丁基或4-羟丁基。
A为C2-C6亚烷基的实例为亚乙基、亚丙基、2，2-二甲基亚丙基、四亚甲基或六亚甲基。
如果R21与R22同时代表C4-C5亚烷基或C4-C5氧杂亚烷基，其实例为四亚甲基、五亚甲基或3-氧杂五亚甲基。
下式化合物为该类多烷基哌啶化合物的实例：
Figure 891048871_IMG24
Figure 891048871_IMG25
f）在重复结构单元中含式（Ⅰ）2，2，6，6-四烷基啶基团的低聚合或高聚合化合物，特别是聚酯、聚醚、聚酰胺、聚胺、聚氨基甲酸乙酯、聚脲、聚氨基三嗪、聚（甲基）丙烯酸酯、聚（甲基）丙烯酰胺及其含上述基团的共聚物。
具有下式的化合物（其中m为2-约200的整数）为该类2，2，6，6，-多烷基哌啶光稳定剂的实例：
Figure 891048871_IMG27
Figure 891048871_IMG29
g）具有式（Ⅸ）化合物：
Figure 891048871_IMG30
其中R和R11的定义与a）中相同。
优选的式（Ⅸ）化合物为其中R为氢或甲基且R11为氢或甲基的化合物。
该类化合物的实例为：
95）2，2，6，6-四甲基-4哌啶酮（四甲基哌啶酮），
96）1，2，2，6，6-五甲基-4-哌啶酮，
97）2，2，6，6-四甲基-4-哌啶酮-1-氧基，
98）2，3，6-三甲基-2，6-二乙基-4-哌啶酮。
根据基油的类型和所需的稳定化程度来确定加到基油（A）中的（B）和（C）的量。一般来说，（B）和（C）的总量为（A）的0.1-2%（重量），优选0.5-1%（重量）。（B）与（C）的比可在较宽的范围内变动，一般（B）在数量上为主要组分（B）与（C）的比最好为3-5∶1。
组分（A）为矿物或合成基油，一般用于制备润滑油。合成油的实例为多元羧酸或多元醇的酯，还可为脂族聚酯或聚α-烯烃、聚硅氧烷、磷酸酯或聚（亚烷基）二醇。润滑油还可在基于油和增稠剂的润滑脂。这样的润滑油的实例可见D.Klamann“Schmier“Schmierstoffe        und        artverwandte        Produkte”[“Lubricants        and        Related        products“VerlagChemie，Weinheim        1982]。
润滑油中还可另含其它添加剂，如其它抗氧化剂、金属钝化剂、防锈剂、粘度指数改进剂、倾点下降剂、分散剂、表面活性剂或抗磨添加剂。
苯酚抗氧化剂的实例：
1.烷基化的一元酚
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-正丁基苯酚、2，6-二叔丁基-4-异丁基苯酚、2，6-二环戊基-4-甲基苯酚、2-（α-甲基环己基）-4，6-二甲基苯酚、2，6-二-十八烷基-4-甲基苯酚、2，4，6-三环己基苯酚、2，6-二叔丁基-4-甲氧甲基苯酚、邻-叔丁基苯酚。
2.烷基化的氢醌
2，6-二叔丁基-4-甲氧基苯酚、2，5-二叔丁基氢醌、2，5-二叔戊基氢醌、2，6-二苯基-4-十八烷氧基苯酚。
3.羟基化硫代二苯基醚
2，2′-硫代-双（6-叔丁基-4-甲基苯酚）、2，2′-硫代-双（4-辛基苯酚）、4，4′-硫代-双（6-叔丁基-甲基苯酚）、4，4′-硫代-双（6-叔丁基-2-甲基苯酚）。
4.亚烷基双酚
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-（α-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（4，6-二叔丁基苯酚）、2，2′-亚乙基-双（4，6-二叔丁基苯酚）、2，2′-二亚乙基-双（6-叔丁基-4-异丁基苯酚或-5-异丁基苯酚）、2，2′-亚甲基-双[6-（α-甲基苄基）-4-壬基苯酚]、2，2′-亚甲基、双[6-（α，α-二甲基苄基）-4-壬基苯酚]、4，4′-亚甲基-双（2，6-二叔丁基苯酚酚）、4，4′-亚甲基-双（6-叔丁基-2-甲基苯酚）、1，1-双（5-叔丁基-4-羟基-2-甲苯基）丁烷、2，6-双（3-叔丁基-5-甲基-2-羟苄基）-4-甲基苯酚、1，1，3-三（5-叔丁基-4-羟基-2-甲基苯基）-3-正十二烷基基丁烷、双[3，3-双（3′-叔丁基-4′-羟基苯基）丁酸]乙二醇酯、双（3-叔丁基-4-羟基-5-甲苯基）-二环戊二烯双[2-（3′-叔丁基-2′-羟基-5′-甲基苄基）-6-叔丁基-4-甲基苯基]对苯二酸酯。
5.苄基化合物
1，3，5-三-（3，5-二叔丁基-4-羟基苄基）-2，4，6-三甲基苯、双-（3，5-二叔丁基-4-羟基苄基）硫醚、3，5-二叔丁基-4-羟苄基-基乙酸异辛酯、双-（4-叔丁基-3-羟基-3-羟基-2，6-二甲基苄基）二硫羟-对苯二酸酯、1，3，5-三-（3，5-二叔丁基-4-羟苄基）异氰脲酸酯、1，3，5-三-（4-叔丁基-3-羟基-2，6-二甲基苄基）异氰脲酸酯、3，5-二叔丁基-4-羟苄基-磷酸二（十八烷基）酯、3，5-二叔丁基-4-羟苄基磷酸单乙基酯的钙盐。
6.酰基氨基苯酚
N-4-羟基月桂酰苯胺、4-羟基硬脂酰苯胺、2，4-双-（辛基）-6-（3，5-二叔丁基-4-羟基苯胺基）-S-三嗪、N-（3，5-二叔丁基-4-羟苯基）氨基甲酸辛酯。
7.β-（3，5-二叔丁基-4-羟苯基）-丙酸的酯
上述酸与一元或多元醇成的酯，何如与甲醇、十二甘醇、十八烷醇、三甘醇1，6-己二醇、季戊四醇、新戊二醇、异氰脲酸三-（（羟乙基）酯、硫代二亚乙基二醇、双（羟乙基）乙二酰胺形成的酯。
8.β-（5-叔丁基-4-羟基-3-甲苯胺）-丙酸的酯。
上述酸与一元或多元醇成的酯，例如与甲醇、二甘醇、十八烷醇、三甘醇、1，6-己二醇、季戊四醇、新戊二醇异氰脲酸三-（羟乙基）酯、硫代二亚乙基二醇、双（羟乙基）乙二酰胺形成的酯。
9.β-（3，5-二叔丁基-4-羟苯基）-丙酸的酰胺
N，N′-双-（3，5-二叔丁基-4-羟苯基丙酰基）六亚甲基二胺、N，N′-双-（3，5-二叔丁基-4-羟苯基丙酰基基）三亚甲基二胺、N，N′-双-（3，5-二叔丁基-4-羟苯基丙酰基）肼。
其它抗氧化剂的实例：
脂族或芳族亚磷酸酯、硫代二丙酸酯、硫代二乙酯酯、二硫代氨基甲酸的盐或二硫代磷酸的盐。
例如铜的金属钝化剂的实例：
三唑、苯并三唑及其衍生物、甲苯三唑及其衍生物、2-基苯并噻唑、2-基苯并三唑、2，5-二基苯并三唑、2，5-二基苯并噻二唑、5，5′-亚甲基-双-苯并三唑、4，5，6，7-四氢苯并三唑、亚水杨基丙邻二胺、水杨基氨基胍及其盐。
防锈剂的实例：
a）有机酸及其酯、金属盐和酐，例如：N-油酰肌氨酸、一油酸山梨醇、环烷酸铅、环烷烯基琥珀酸酐，如十二碳烯琥珀酸酐，烯基琥珀酸半酯和半酰胺，以及4-壬基苯氧乙酸。
b）含氮化合物，例如
Ⅰ.脂族或环脂族伯、仲或叔胺以及有机和无机酸的胺盐，例如油溶性烷基羧酸铵。
Ⅱ.杂环化合物，例如取代的咪唑啉和噁唑啉。
c）含磷化合物，如磷酸偏脂的胺盐或膦酸偏脂的胺盐，二烷基二硫代磷酸锌。
d）含硫化合物，如二壬基萘磺酸钡，石油磺酸钡。
粘度指数改进剂的实例：
聚丙烯酸酯、聚甲基丙烯酸酯、乙烯基吡咯烷酮/甲基丙烯酸酯共聚物、聚乙烯基吡咯烷酮、聚丁烯、烯烃共聚物、苯乙烯/丙烯酸酯共聚物、聚醚。
倾点下降剂的实例：
聚甲基丙烯酸酯、烷基化萘衍生物。
分散剂/表面活性剂的实例：
聚丁烯基琥珀酰胺或聚丁烯基琥珀酰亚胺、聚丁烯基磷酸衍生物碱性磺酸和苯酚的镁、钙和钡盐。
抗磨添加剂的实例：
含有硫和/或磷和/或卤素的化合物，如硫化植物油、二烷基二硫代磷酸锌、磷酸三甲酸酯、氯代石蜡、烷基硫、芳基二硫和芳基三硫、硫代硫酸偶磷三苯酯、二乙醇氨基甲基甲苯基三唑、二（2-乙基己基）氨基甲基甲苯基三唑。
加入苯酚型抗氧化剂和/或具有提高组分（B）和（C）稳定作用的脂族和芳族亚磷酸酯或        亚膦酸酯（phosphonites）是非常重要的。
适宜的亚磷酸酯和        亚膦酸酯的实例为：
亚磷酸三苯酯、亚磷酸癸基二苯酯、亚磷酸苯基二癸酯、亚磷酸三（壬苯基）酯，亚磷酸三月桂酯、亚磷酸三（十八烷基）酯、二亚磷酸二硬脂酰季戊四醇酯、亚磷酸三（2，4-二叔丁基苯基）酯、二亚磷酸二异癸基季戊四醇酯、二亚磷酸双（2，4-二叔丁基苯基）-戊基四醇酯、三亚磷酸三硬脂山梨醇酯、4，4′-亚联苯基二                亚膦酸四-（2，4-二叔丁苯基）酯以及二亚磷酸二（2，6-二叔丁基-4-甲苯基）季戊四醇酯。
将各个添加剂溶于油中。为加速溶解，可先将油预热，也可先将添加剂溶于溶剂中。
润滑油中还可含固体润滑油添加剂，如石墨或硫化钼。
下述实施例更详细地说明本发明。除非另有说明者外，份数和百分比均以重量计。
实施例1
在等温条件下，用差示扫描量热计（Du Pont热分析仪1090）通过含400ppmNO2的空气确定油样的氧化诱导期测量是在170℃温度和8巴压力下进行的。用一种含有1%（体积1-癸烯的矿物油（Aral136）作参比基油。加入1-癸烯的目的是提高其对氧化作用的敏感性。在油中加入下述胺稳定剂。
芳香胺：
A-1        二苯胺与二异丁烯反应所得到的工业混合物，其中含有
a）3%二苯胺，
b）14%4-叔丁基二苯胺，
c）30%4-叔辛基二苯胺、4，4′-二叔丁基二苯胺和2，4，4′-三叔丁基二苯胺，
d）29%4-叔丁基-4′-叔辛基二苯胺、2，2′-和3，3′-二叔辛基二苯胺和2，4-二叔丁基-4′-叔辛基二苯胺，
e）18%4，4′-二叔辛基二苯胺，
f）6%2，4-二叔辛基-4′-叔丁基二苯胺。
A-2        3，7-二-（叔辛基）噻吩嗪
位阻胺：
H-1        癸二酸二（2，2，6，6-四甲基啶-4-基）酯
H-2        2，2，6，6-四甲基-4-啶酮
H-3        丁二酸二（2，2，6，6-四甲基啶-4-基）酯
H-4        癸二酸二（1，2，2，6，6-五甲基啶-4-基基）酯
H-5        2，3，6-三甲基-2，6-二乙基啶酮
H-6        2，2，6，6-四甲基-4-丁基氨基啶
表1列出了诱导期。诱导期越长，稳定剂添加剂的抗氧化作用越强。
表1
芳香胺        位阻胺        诱导期（分钟）
-        -        43
0.55%        A-1        -        80
0.45%        A-1        0.10%        H-1        91.5
0.45%        A-1        0.10%        H-2        91.5
0.45%        A-1        0.10%        H-3        90.05
0.45%        A-1        0.10%        H-4        90
0.45%        A-1        0.10%        H-5        84.5
0.45%        A-1        0.10%        H-6        89
实施例2
烃类的氧化会使其含氧基团（如羟基、羧基或酯基）增加。红外光谱可测定这些基团的量并由此确定抗氧化剂的效果。为达到此目的将含有1%（体积）1-癸烯（加入1-癸烯的目的是提高其对氧化作用的敏感性）的参比矿物油（Aral
Figure 891048871_IMG31
136）油样于等温和8巴压力条件下，在含400ppm NO2的空气中加热12小时。然后测定于1730厘米-1和1630厘米-1的红外吸收。该值越大，稳定剂的作用越强。表2a和表2b列出了各种温度下的实验结果。
表2a-于120℃氧化
红外吸收
稳定剂 于1730厘米-1于1630厘米-1
0.55%        A-1        0.471        1.051
0.45%        A-1+0.10%        H-2        0.392        0.839
0.45%        A-1+0.10%        H-3        0.424        0.863
0.45%        A-1+0.10%        H-5        0.396        0.673
表2b-于150℃氧化
红外吸收
稳定剂 于1730厘米-1于1630厘米-1
0.55%        A-1        0.557        1.851
0.45%        A-1+0.10%        H-4        0.353        1.500
0.65%        A-1        0.384        1.599
0.45%        A-1+0.10%        H-4
+0.10% 酚 R＊） 0.330 1.279
0.45%        A-1+0.10%        A-2
+0.10%        H-4        0.340        1.443
＊）酚B＝具有下式的化合物
Figure 891048871_IMG32
实施例3
根据ASTM        D-943的TOST（汽轮机氧化稳定性试验验）方法测定本发明稳定润滑油的氧化物特性。为达到此目的，将60毫升水加到300毫升矿物油（Mobil        STOC        K        305）中，然后在有铁或铜丝的存在下于95℃加热该油1000小时，同时通入氧气。通过测定中和值TAN（毫克KOH/克油）和淤渣生成量来确定测量参数，即酸的生成。
为达到稳定的目的，可单独使用胺A-1，也可使用A1与位阻胺H-7（2，2，6，6-四甲基-4-十二烷氧基啶）的混合物。稳定剂的总浓度均为0.25%（基于润滑油）。
表3
A-1        H-7        TAN（毫克KOH/克油）淤渣（毫克）
100%        0.46        30
95%        5%        0.38        27
90%        10%        0.30        24
75%        25%        0.31        27
实施例4
与实施例1相似，于170℃测定氧化诱导期。使用了下述位阻胺：
H-8        N，N′-双（2，2，6，6-四甲基哌啶-4-基六亚甲基二胺
H-9        N，N′-双（2，2，6，6-四甲基哌啶-4-基五亚甲基二胺
H-10        4-（甲氧丙氨基）-2，2，6，6-四甲基哌啶
表4
芳香胺        位阻胺        诱导期（分钟）
-        -        48
0.55%        A-1        -        86
0.45%        A-1        0.10%        H-8        95
0.45%        A-1        0.10%        H-9        96
0.45%        A-1        0.10%        H-10        89
实施例5
按实施例1所述的方法测定170℃氧化诱导期。使用下述芳香胺：
A-3        N-（对辛基苯基）-1-萘胺
表5
芳香胺        位阻胺        诱导期（分钟）
0.55%        A-3        -        52.8
0.45%        A-3        0.10%        H-7        66
实施例6
通过测定于高温下用氧处理润滑油时的粘度增长同样可以确定抗氧化性能。
为达到此目的，于150℃下将氧气流（1升/小时）通过润滑油70小时。先加入催化量的环烷酸酮提高润滑油对氧化作用的敏感性。用Ubbelode粘度计测量润滑油于氧化前后的粘度。
表6
润滑油        粘度增长百分比
基油        168%
含0.6%        A-1和0.15%
H-8的基油        3.4%

Claims (15)

1、一种润滑油组合物，其中包括
(A)一种矿物或合成基础油或这些油的混合物；
(B)至少一种通式I或Ⅱ的芳香胺，
Figure 891048871_IMG1
其中，R1是C1-18烷基、C7-9苯烷基、C5-12环烷基苯基、C7-8烷苯基、C7-18烷氧苯基或萘基，R2是苯基、C7-18烷基苯基、C7-18烷氧基苯基或萘基，R3是氢、C1-12烷基、苄基、烯丙基、甲基烯丙基、苯基或基团-CH3RS4，R4是C4-18烷基、-CH2COO(C4-18烷基)或-CH2CH2COO(C4-18烷基)，R5和R6各自为H、C1-18烷基或C7-9苯基烷基；和
(C)至少一种位阻胺。
2、权利要求1的组合物，其中含有至少一种作为组分（B）的通式Ⅰ或Ⅱ的化合物，其中R1是C1-4烷基、C7-9苯基烷基环己基、苯基、C10-18烷基苯基或萘基，R2是C10-18烷基苯基或苯基，R3是H、C1-8烷基、苄基、烯丙基或基团-CH2SR4，R4是C8-18烷基或-CH2COO（C8-18烷基），R5和R6各自为C1-12烷基或C7-9苯基烷基。
3、权利要求1的组合物，其中含有至少一种作为组分（B）的通式（Ⅰ）的化合物，其中R1和R2各自为苯基或C10-18烷基苯基，R3是H。
4、权利要求1的组合物，其中含有至少一种作为组分B的通式（Ⅱ）的化合物，其中R3是H，R5和R6各自为H或C4-12烷基。
5、权利要求1的组合物，其中含有作为组分（B）的4，4′-二叔辛基二苯胺、3，7-二叔辛基吩噻嗪或二苯胺与二异丁烯反应得到的工业混合物。
6、权利要求1的组合物，其中含有作为组分（C）的一种含有至少一个通式Ⅲ表示的基团的化合物，
Figure 891048871_IMG2
其中，R是H或甲基。
7、权利要求6的组合物，其中R是H。
8、权利要求6的组合物，其中含有一种作为组分（C）的通式Ⅳ的化合物
其中R是H，R11是H或甲基，n是2，R12是具有4-12个碳的脂族二羧酸的二酰基。
9、权利要求6的组合物，其中含有一种作为组分（B）的通式Ⅴ的化合物
Figure 891048871_IMG4
其中，n是1或2，R是H，R11是H或甲基，R13是H、C1-12烷基或下列通式的基团
其中当n是1时，R14是H或C1-12烷基，当n＝2时，R14是C2-8亚烷基。
10、权利要求6的组合物，其中含有一种作为组分（C）的通式（Ⅸ）的化合物。
Figure 891048871_IMG6
其中R是H或甲基，R11是H或甲基。
11、权利要求1的组合物，其中（B）和（C）的总量为0.0.1～2%（重量）（以（A）为基准）。
12、权利要求1的组合物，其中（B）和（C）的比是每重量份（C）3～5重量份（B）。
13、权利要求1的组合物，其中含有酸型抗氧化剂（D）。
14、权利要求1的组合物，其中含有脂族或芳族亚磷酸酯（phosphite）或亚膦酸酯（phosphonite）（E）。
15、使用权利要求1的组合物作机油。
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MX169536B (es) 1993-07-09
EP0356677A1 (de) 1990-03-07

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