CN1028243C - 润滑油组合物 - Google Patents
润滑油组合物 Download PDFInfo
- Publication number
- CN1028243C CN1028243C CN90103183A CN90103183A CN1028243C CN 1028243 C CN1028243 C CN 1028243C CN 90103183 A CN90103183 A CN 90103183A CN 90103183 A CN90103183 A CN 90103183A CN 1028243 C CN1028243 C CN 1028243C
- Authority
- CN
- China
- Prior art keywords
- alkyl
- base
- formula
- hydrogen
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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Abstract
用添加a)一种位阻胺和b)一种式I酚的方法可使润滑油具有抗氧化稳定性。
式中A、B和X的定义同权利要求1。所用的式I酚最好是含有硫醚基。
Description
本发明涉及抗氧化降解稳定性润滑油组合物。所述的稳定性是靠加入至少两种特定添加剂实现的。
众所周知,为了改善矿物油基或合成油基润滑油的一般使用性质,习惯于把一些添加剂加入这些润滑油中。使润滑油具有抗氧化降解稳定性用的添加剂叫做抗氧化剂,这是一类特别重要的添加剂。润滑油的氧化降解,就发动机润滑油而言,是特别值得注意的,因为在发动机的燃烧室中经常发生高温,又有氧气和氮的氧化物(NOX)存在并起着氧化催化剂的作用。
具体地说,用于润滑油的抗氧化剂有有机硫化合物和有机磷化合物,还有芳族胺和酚,特别是位阻酚(例如见Ullmanns Encyklopadie der technishen Chemie(Ullmann′s化学工艺大全),第四版,Verlag Chemie,卷20(1981),P541~43)。
位阻胺也已被推荐为润滑油用稳定剂,例如在US4,069,199或JP-A-85/28496中。
EP-A-356 677已推荐芳族胺和位阻胺的混合物为润滑油用抗氧化剂,还可以将酚抗氧化剂加入上述混合物中。
现已发现,酚抗氧化剂和位阻胺的混合物特别适宜于提高润滑油和稳定性,即使不加芳族胺,也是如此。
本发明涉及一种包含下列组分的润滑油组合物:
(A)一种矿物油或合成油或其混合物;
(B)至少一种位阻胺;和
(C)至少一种式Ⅰ的酚,
式中A为氢C1~C24烷基、C5~C12环烷基、C7~C9苯基烷基、苯基或-CH2-S-R1基或基
B为C1~C24烷基、C5~C12环烷基、C7~C9苯基烷基、苯基或-CH2-S-R1基,X为氢、C1~C18烷基或-CaH2a-Sq-R2基、-Cb-H2b-CO-OR3基、-Cb-H2b-CO-N(R5)(R6)基、-CH2N(R10)(R11)基和下式基之一,
R1为C1~C18烷基、苯基或-(CH2)C-CO-OR4基或-CH2CH2OR9基,R2为氢、C1~C18烷基、苯基、苄基或基
R3为C1~C50烷基或下述基之一,所述基是
其中Q为C2~C8亚烷基、C4~C6硫杂亚烷基或-CH2CH2(OCH2CH2)d-基,R4为C1~C24烷基,R5为氢、C1~C18烷基或环己基,R6为C1~C18烷基、环己基、苯基、C1~C18烷基取代苯基或下式基中的一个,
或R5和R6一起形成可被-O-或-NH-断开的C4~C8亚烷基,R7为氢、C1~C4烷基、苯基、R8为C1~C18烷基,R9为氢、C1~C2烷基、苯基C2~C18链烷酰或苯甲酰基,R10为C1~C18烷基、环己基、苯基、C1~C18烷基取代苯基或基
或R10和R11一起形成可被-O-或-NH-断开的C4~C8亚烷基,a为0、1、2或3,d为0、1、2或3,c为1或2,d为1~5,f为2~8和9为1、2、3或4;或作为组分(c)的为多酚的混合物,这种多酚的混合物是通过使至少一种下式酚
与至少一种下式酚
以及与甲醛或对甲醛反应制得的,其中C、D和E各自为C1~C24烷基、环己基或苯基,这种组合物不含芳族胺。
上述组合物中(B)对(C)的重量比最好是1∶3~1∶100。尤其是1∶3~1∶20,(B)和(C)之和最好是(A)的0.05~5%(重量),尤其是(A)的0.1~3%(重量)。
A和B代表的C1~C24烷基可以是直链的或支链的烷基,例如甲基、乙基、异丙基、叔丁基、仲丁基、仲戊基、叔戊基、正己基、异己基、叔己基、异庚基、正辛基、叔辛基、仲癸基、仲十二烷基、正十二烷基、仲十四烷基、正十六烷基、正十八烷基、仲十八烷基或正二十烷基。
A和B代表的环烷基可以是,例如环戊基、环己基或环辛基,尤其是环己基。A和B代表的苯基烷基可以是,例如苄基、苯基乙基、苯基丙基或α,α-二甲基苄基。
R5和R6代表的C1~C12烷基可以是,例如甲基、乙基、丙基、丁基、戊基、己基、辛基、癸基或十二烷基。R1、R2、R3和R8代表的C1~C18烷基时还可以是,例如十四烷基、十六烷基或十八烷基。R4代表的C1~C24烷基时还可以是,例如二十烷基或二十四烷基。
注脚a最好是0、1或2,特别是0或1;b最好是0、1或2,特别是1或2;q最好是1或2,特别是1。
组分(A)是通常用于制备润滑油的矿物基油或合成基油。合成油可以是例如多羧酸的或多醇的酯、脂族聚酯或聚a-烯烃、硅氧烷磷酸酯或聚亚烷基二醇。润滑油也可以是基于油和增稠剂的润滑脂。例如在D.Klamann著的“润滑剂及发展出的相关产品”(“Schmier-stoffe und artverwandte Produkte”)(Velag Chemie,Weinheim,1982)一书中对上述润滑油作了描述。
组分(B)可以是任何环状的或非环状的位阻胺,最好是环状的位阻胺。(B)最好是含有至少一个式Ⅱ基的化合物
式中R为氢或甲基。R最好为氢。上述化合物是多烷基哌啶的衍生物,尤其是2,2,6,6-四甲基哌啶的衍生物。这些化合物最好是在哌啶环的4-位上带有一或二个极性取代基或一个极性螺环体系。它们可以是低分子量的低聚物或聚合物。
特别重要的多烷基哌啶有以下几类:
a)式Ⅲ化合物
式中n为1~4,最好为1或2,R为氢或甲基;R11为氢、氧基、羟基、C1~C12烷基、C3~C8链烯基、C3~C8炔基、C7~C12芳烷基、C1~C18烷氧基、C5~C8环烷氧基C7~C9苯基烷氧基、C1~C18链烷酰、C3~C5链烯酰、C1~C18链烷酰氧基、苄氧基、缩水甘油基或-CH2CH(OH)-Z基,其中Z为氢、甲基或苯基,R11最好是氢、C1~C4烷基,烯丙基、苄基、乙酰或丙烯酰;和R12当n为1时为氢,可被一个或多个氧原子断开的C1~C18烷基,氰基乙基,苄基,缩水甘油基,脂族的、环脂族的、芳脂族的、不饱和或芳族的羧酸氨基甲酸或含磷酸的一价基,或一价的甲硅烷基,最好是具有2~18个碳原子的脂族羧酸的基、具有7~15个碳原子的环脂族羧酸的基、具有3~5个碳原子的α,β-不饱和羧酸的基或具有7~15个碳原子的芳族羧酸的基,R12当n为2时为C1~C12亚烷基,C4~C12亚烯基,亚二甲苯基,脂族的、环脂族的、芳脂族的或芳族的二羧酸、二(氨基甲酸)或含磷酸的二价基,或二价的甲硅烷基,最好是具有2~36个碳原子的脂肪二羧酸的基、具有8~14个碳原子的环脂族或芳族二羧酸的基或具有8~14个碳原子的脂族、环脂族或芳族的二(氨基甲酸)的基,R12当n为3时为脂族的、环脂族的或芳族的三羧酸的三价基、芳族的三(氨基甲酸)的三价基或含磷酸的三价基、或三价的甲硅烷基,和R12当n为4时为脂族的、环脂族的或芳族的四羧酸的四价基。
任何C1~C12烷基取代基是,例如甲基、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。
R11或R12代表的C1~C18烷基可以为例如上述基,还可以为例如正十三烷基、正十四烷基、正十六烷基或正十八烷基。
R11代表的C3~C8链烯基可以是,例如1-丙烯基、烯丙基、甲基烯丙基、2-丁烯基、2-戊烯基、2-己烯基、2-辛烯基或4-叔丁基-2-丁烯基。
R11代表的C3~C8链炔基最好为炔丙基。
R11代表的C7~C12芳烷基最好为苯乙基,特别是苄基。
R11代表的C7~C8链烷酰是,例如甲酰、丙酰、丁酰或辛酰,但最好是乙酰,和R11代表的C3~C5链烯酰最好是丙烯酰。
R12代表的羧酸的一价基是,例如乙酸基、癸酸基、硬脂酸基、丙烯酸基、甲基丙烯酸基、苯甲酸基或β-(3,5-二叔丁基-4-羟苯基)丙酸基。
R12代表的二羧酸的二价基是,例如丙二酸基、丁二酸基、戊二酸基、己二酸基、辛二酸基、癸二酸基、顺式丁烯二酸基、亚甲基丁二酸基、二丁基丙二酸基、二苄基丙二酸基、丁基(3,5-二叔丁基-4-羟基苄基)丙二酸基或二环庚烯二羧酸基。
R12代表的三羧酸的三价基是,例如1,2,4-苯三酸基、柠檬酸基或次氮基三乙酸基。
R12代表的四羧酸的四价基是,例如丁烷-1,2,3,4-四羧酸的四价或1,2,4,5-苯四酸的四价基。
R12代表的二(氨基甲酸)的二价基是,例如六亚甲基二(氨基甲酸)基或2,4-甲苯二(氨基甲酸)基。
优选的式Ⅲ化合物是其中的R是氢,R11是氢或甲基,n是1和R12是C1~C18烷基,或n
是2和R12是具有4~12个碳原子的脂族二羧酸的二酰基。
下列化合物是这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
7)4-甲基丙烯酰氧基-1,2,2,6,6-五甲基哌啶
8)β-(3,5-二叔丁基-4-羟基苯基)丙酸1,2,2,6,6-亚甲基哌啶-4-基酯
9)丙二酸二(1-苄基-2,2,6,6-四甲基哌啶-4-基)酯
10)丁二酸二(2,2,6,6-四甲基哌啶-4-基)酯
11)戊二酸二(2,2,6,6-四甲基哌啶-4-基)酯
12)己二酸二(2,2,6,6-四甲基哌啶-4-基)酯
13)癸二酸二(2,2,6,6-四甲基哌啶-4-基)酯
14)癸二酸二(1,2,2,6,6-五甲基哌啶-4-基)酯
15)癸二酸二(1,2,3,6-四甲基-2,6-二乙基哌啶-4-基)酯
16)苯二酸二(1-烯丙基-2,2,6,6-四甲基哌啶-4-基)酯
17)1-羟基-4-β-氰基乙氧基-2,2,6,6-四甲基哌啶
18)乙酸1-乙酰-2,2,6,6-四甲基哌啶-4-基酯
19)1,2,4-苯三酸三(2,2,6,6-四甲基哌啶-4-基)酯
20)1-丙烯酰-4-苄氧基-2,2,6,6-四甲基哌啶
21)二乙基丙二酸二(2,2,6,6-四甲基哌啶-4-基)酯
22)二丁基丙二酸二(1,2,2,6,6-五甲基哌啶-4-基)酯
23)丁基(3,5-二叔丁基-4-羟基苄基)丙二酸二(1,2,2,6,6-五甲基哌啶-4-基)酯
24)癸二酸二(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)酯
25)癸二酸二(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)酯
26)己烷-1′6′-二(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′-二(4-氨基甲酰氧基-1-正丙基-2,2,6,6-四甲基哌啶)
28)二甲基二(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-基)硅烷
30)亚磷酸三(1-丙基-2,2,6,6-四甲基哌啶-4-基)酯
31)磷酸三(1-丙基-2,2,6,6-四甲基哌啶-4-基)酯
32)膦酸苯基[二(1,2,2,6,6-五甲基哌啶-4-基)]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-羟基丙基)-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Ⅳ化合物
式中n为1或2,R和R11的定义同a),R13为氢、C1~C18烷基、C2~C5羟烷基、C5~C7环烷基、C7~C8芳烷基、C2~C18链烷酰、C3~C5链烯酰、苯甲酰基或下式基
和R14当n为1时为氢,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、缩水甘油基或式-CH2-CH(OH)-Z基或式-CONH-Z基取代的C1~C4烷基,其中Z为氢、甲基或苯基,R14当n为2时为C2~C12亚烷基、C6~C12亚芳基、亚二甲苯基、-CH2-CH(OH)-CH2-基或-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,或如果R13不是链烷酰、链烯酰或苯甲酰,则R14也可为脂族的、环脂族的或芳族的二羧酸或二(氨基甲酸)的二价基、或-CO-基,或R13和R14当n为1时一起为脂族的、环脂族的或芳族的1,2-或1,3-二羧酸的二价基。
任何C1~C12或C1~C18烷基取代基的定义均与上述a)中所述的相同。
任何C5~C7环烷基取代基最好为环乙基。
R13代表的C7~C8芳烷基最好苯基乙基或尤其是苄基。
R13代表的C2~C5羟烷基最好为2-羟乙基或2-羟丙基。
R13代表的C2~C18链烷酰为,例如丙酰、丁酰、辛酰、十二烷酰、十六烷酰或十八烷酰,但最好为乙酰;和R13代表的3~5链烯酰最好为丙烯酰。
R14代表的C2~C8链烯基为,例如烯丙基、甲基烯丙基、2-丁烯基、2-戊烯基、2-己烯基或2-辛烯基。
R14代表的被羟基、氰基、烷氧羰基或脲基取代的C1~C4烷基可以为,例如2-羟乙基、2-羟丙基、2-氰基乙基、甲氧基羰基甲基、2-乙氧基羰基乙基、2-氨基羰基丙基或2-(二甲基氨基羰基)乙基。
任何C2~C12亚烷基取代基为,例如1,2-亚乙基、1,3-亚丙基、2,2-二甲基-1,2-亚丙基、1,4-亚丁基、1,6-亚己基、1,8亚辛基、1,10-亚癸基或1,12-亚十二烷基。
任何C6~C15亚芳基取代基为,例如邻亚苯基、间亚苯基或对亚苯基、1,4-亚萘基或4,4′-二亚苯基。
D代表的C6~C12亚环烷基最好为环亚己基。
优选的Ⅳ化合物是其中n为1或2,R为氢,R11为氢或甲基,R13为氢、C1~C12烷基或下式基
和R14在n=1的情况下为氢或C1~C12烷基,和在n=2的情况下为C2~C8亚烷基。
下列化合物是这类多烷基哌啶化合物的实例:
37)N,N′-二(2,2,6,6-四甲基哌啶-4-基)六亚甲基-1,6-二胺
38)N,N′-二(2,2,6,6-四甲基哌啶-4-基)六亚甲基-1,6-二乙酰胺
39)二(2,2,6,6-四甲基哌啶-4-基)胺
40)4-苯甲酰氨基-2,2,6,6-四甲基哌啶
41)N,N′-二(2,2,6,6,-四甲基哌啶-4-基)-N,N′-二丁基己二酰二胺
42)N,N′-二(2,2,6,6,-甲基哌啶-4-基)-N,N′-二环己基-2-羟亚丙基-1,3-二胺
43)N,N′-二(2,2,6,6,-四甲基哌啶-4-基)对亚二甲苯二胺
44)N′,N′-二(2,2,6,6,-四甲基哌啶-4-基)丁二酰二酰胺
45)N-(2,2,6,6,-四甲基哌啶-4-基)-β-氨基二丙酸二(2,2,6,6,-四甲基哌啶-4-基)酯
46)下式化合物
47)4,4-二(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-叔丁基苯甲酰氨基)-2,2,6,6-四甲基哌啶
49)4-甲基丙烯酰氨基-1,2,2,6,6-五甲基哌啶
c)式Ⅴ化合物
式中n为1或2,R和R11的定义同a)所述,和R15当n为1时为C2~C8亚烷基、C2~C8羟亚烷基或C4~C22酰氧基亚烷基,和当n为2时为(-CH2)2C(CH2-)2基。
R15代表的C2~C8亚烷基或C2~C8羟亚烷基为,例如1,2-亚乙基、1-甲基-1,2-亚乙
基、1,3-亚丙基、2-乙基-1,3-亚丙基或2-乙基-2-羟甲基-1,3-亚丙基。
R15代表的C4~C22酰氧基亚烷基为,例如2-乙基-2-乙酰氧基甲基-1,3-亚丙基。
下列的化合物是这类多烷基哌啶化合物的实例:
50)9-氮杂-8,8,10,10-四甲基-1,5-二氧杂螺[5,5]十一烷
51)9-氮杂-8,8,10,10-四甲基-3-乙基-1,5-二氧杂螺[5,5]十一烷
52)8-氮杂-2,7,7,8,9,9-六甲基-1,4-二氧杂螺[4.5]癸烷
53)9-氮杂-3-羟甲基-3-乙基-8,8,9,10,10-五甲基-1,5-二氧杂螺[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-1,5-二氧杂螺[5.5]十一烷
55)2,2,6,6-四甲基哌啶-4-螺-2′-(1′,3′-二氧杂环己烷)-5′-螺-5″-(1″,3″-二氧杂环己烷)-2″-螺-4-″′-(2-″′,2″′,6″′,6″′-四甲基哌啶)
d)式ⅥA、ⅥB和ⅥC化合物
式中n为1或2,R和R11的定义同上述a)所述,R16为氢、C1~C12烷基、烯丙基、苄基、缩水甘油基或C2~C6烷氧基烷基,R17当n为1时为氢、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烷氧基烷基、C6~C10芳基、缩水甘油基或式-(CH2)p-COO-Q基或式-(CH2)p-O-CO-Q基,其中p为1或2和Q为C1~C4烷基或苯基,和R17当n为2时为C2~C12亚烷基、C2~C12亚链烯基、C6~C12亚芳基、式-CH2-CH(OH)-CH2-O-D-OCH2-CH(OH)-CH2-,其中D为C2~C10亚烷基、C6~C15亚芳基或C6~C12亚环烷基或-CH2CH(OZ′)CH2-(OCH2-CH(OZ′)CH2)2-基,其中Z′为氢、C1~C18烷基、烯丙基、苄基、C2~C12链烷酰或苯甲酰,和T1与T2各自为氢、C1~C18烷基或C6~C10芳基或未取代或被卤素或C1~C4烷基取代的C7~C9芳烷基,或T1与T2与连接它们碳原子形成C5~C12环烷环。
任何C1~C12烷基取代基为,例如甲基、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、正十一烷基和正十二烷基。
任何C1~C18烷基取代基可以是,例如上述的基,还可以是例如正十三烷基、正十四烷基、正十六烷基和正十八烷基。
任何C2~C6烷氧基烷基取代基为,例如甲氧基甲基、乙氧基甲基、丙氧基甲基、叔丁氧基甲基、乙氧基乙基、乙氧基丙基、正丁氧基乙基、叔丁氧基乙基、异丙氧基乙基或丙氧基丙基。
R17代表的C3~C5链烯基为,例如1-丙烯基、烯丙基、甲基烯丙基、2-丁烯基或2-戊烯基。
R17、T1和T2代表的C7~C9芳烷基最好为苯乙基或特别是苄基。如果T1和T2与碳原子形成环烷环,该环可以为,例如环戊烷环、环己烷环、环辛烷环或环十二烷环。
R17代表的C2~C4羟烷基为,例如2-羟乙基、2-羟丙基、2-羟丁基或4-羟丁基。
R17、T1和T2代表的C6~C10芳基最好为未取代或被卤素或C1~C4烷基取代的苯基或α-或β-萘基。
R17代表的C2~C12亚烷基为,例如1,2-亚乙基、1,2-亚丙基、2,2-二甲基-1,2-亚丙基、1,4-亚丁基、1,6-亚己基、1,8-亚辛基、1,10-亚癸基或1,12-亚十二烷基。
R17代表的C4~C12亚链烯基最好为1,4-亚丁烯基、1,5-亚戊烯基或1,6-亚己烯基。
R17代表的C6~C12亚芳基为,例如邻亚苯基、间亚苯基或对亚苯基、1,4-亚萘基或4,4′-二亚苯基。
Z′代表的C2~C12链烷酰为,例如丙酰、丁酰、辛酰或十二烷酰,但最好是乙酰。
D代表的C2~C10亚烷基、C5~C15亚芳基或C6~C12亚环烷基同上述67的定义。
下列化合物是这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-1,3,8-三氮杂-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)缩水甘油基-1,3,8-三氮杂-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-氧代螺[5.1.11.2]-二十烷
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-3-十二烷基-1,3,8-三氮杂-7,7,9,9-四甲基螺[4.5]癸烷-2,4二酮或下式的化合物
e)式Ⅶ化合物
式中n为1或2,R18为下式基
式中R和R″的定义同a)中所述,E为-O-或-NH21-,A为C2~C6亚烷基或-(CH2)3-O-和X为O或1,R19与R18相同,或为-NR21R22、-OR23、-NHCH2OR23和-N(CH2OR23)2中的一个,R20当n=1时与R18或R19相同,和当n为2时为-E-B-E-基,其中B为可被-N(R21)-断开的C2-C6亚烷基,R21为C1~C12烷基、环己基、苄基、C1~C4羟烷基或下式基:
R22是C1~C12烷基、环己基、苄基或C1~C4羟烷基,和R23为氢、C1~C12烷基或苯基,或R21和R22一起为C4~C5亚烷基或C4~C5氧杂亚烷基,例如
基,或R21和R22各为下式基
任何C1~C12烷基取代基为,例如甲基、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。
任何C1~C4羟烷基取代基为,例如2-羟乙基、2-羟丙基、3-羟丙基、2-羟丁基或4-羟丁基。
A代表的C2~C6亚烷基为,例如1,2-亚乙基,1,3-亚丙基、2,2-二甲基-1,3-亚丙基,1,4-亚丁基或1,6-亚己基。
如果R21和R22一起形成C4~C5亚烷基或C4~C5氧杂亚烷基,那其可为例如1,4-亚丁基、1,5-亚戊基或3-氧杂-1,5-亚戊基。
下列诸式的化合物是这类多烷基哌啶化合物的实例:
f)重复结构单元含有通式(Ⅰ)2,2,6,6-四烷啶哌基的低聚物或聚合物,特别是聚酯、聚醚、聚酰胺、聚胺氨酯、聚脲、聚氨基三嗪、聚(甲基)丙烯酸酯、聚(甲基)丙酰胺和含有上述基的共聚物。
下列诸式所示的化合物是这类2,2,6,6-多烷基哌光稳剂的例子,式中m为2到约200。
g)式Ⅷ化合物
式中R和R″的定义与上述a)所述的相同。
优选的式Ⅷ化合物是其中R为氢或甲基和R″为氢或甲基的化合物。
这类化合物的实例有:
95)2,2,6,6-四甲基哌啶-4-酮(三丙酮胺)
96)1,2,2,6,6-五甲基哌啶-4-酮
97)1-氧基-2,2,6,6-四甲基哌啶-4-酮
98)2,3,6-三甲基-2,6-二乙基哌啶-4-酮多烷基哌啶是人们熟悉的化合物,并被用作有机材料的光稳剂。其中的一些可由市场购得。
组分(C)是一种酚抗氧化剂。(C)最好是式(Ⅰ)化合物,其中的A为氢、C1~C8烷基、环己基、苯基或下式基
B是C1~C8烷基、环己基或苯基,X为C1~C8烷基,或为-CaH2a-S-R2基、-CbH2b-COOR3基、-CH2N(R10)(R11)基和下式其中的一个
R2为C1~C12烷基、苯基或-(CH2)c-COOR4、R8为C1~C18烷基或下式基
其中Q为C2~C6亚烷基、-CH2CH2SCH2CH2-基或-CH2CH2(OCH2CH2)d-基,R4为C1~C18烷基,R10和R11各自为C1~C12烷基或R10和R11一起为1,5-亚戊基或3-氧杂-1,5-亚戊基,a为1或2,b为1或21C为1或2和d为1~3,或
(c)为下式酚
和(对)甲醛的反应混合物,上面诸式中,C、D和E各自为C1~C8烷基。
一类特别适用作组分(C)的化合物包括式(Ⅰ)化合物,其中的A和B各自为C1~C4烷基,X为-CaH2a-Sq-R2基,a为0或1,q为1或2,R2为C4~C18烷基。苯基或-CH2-CO-OR4基和R4为C1-C18烷基。最好的式Ⅰ化合物是其中的A和B各自为C1~C4烷基,X为-CH2-S-R2基,R2为C8~C12烷基或-CH2-CO-OR4基和R4为C8~C18烷基。在这类化合物中,特别优选的式Ⅰ化合物是其中A和B为叔丁基和X为-CH2SCH2COO(C8~C13烷基)的。
另一类特别适宜作组分(C)的化合物包括式Ⅰ化合物,其中A和B各自为C1~C4烷基,X为-CbH2b-CO-OR3基,b为1或2和R3为下列各基之一。
特别是其中X为-(CH2)3-CO-OR3基和R3为下式基的式Ⅰ化合物。
另一类特别适宜作组分(C)的化合物包括下式所示的亚甲基双酚
式中A、B和X各自为C1~C4烷基。
与至少一种下式所示的一烷基酚
和甲醛或对甲醛反应所得到的多酚混合物,以上各式中C、D和E各自为C1~C4烷基。
由上述反应产生的混合物主要含有双酚和三酚。
式Ⅰ化合物的实例有:4-(4-羟基-3,5-叔丁基苯基)-3-硫杂丁酸三癸酸、3-硫杂-1,5-戊二醇二[3-(4-羟基-3,5-二叔丁基苯基)]丙酸酯、二(4-羟基-3,5-二叔丁基苯基)丙二酸二(3-硫杂十五烷基)酯、4-(4-羟基-3,5-二叔丁基苯基)-3-硫杂丁酸十八烷基酯、4-(2-硫杂丙基)-2,6-二叔丁基酚、3-(4-羟基-3,5-二叔丁基苯基)丙酸十八烷基酯、3-(4-羟基-3,5-二叔丁基苯基)丙酸3-硫杂十五烷基酯、二(4-羟基-3,5-二叔丁基苯基)硫、二(4-羟基-3,5-二叔丁基苯基)二硫、2,4-二(辛基硫代甲基)-6-甲基酚、N-十八烷基-3-(4-羟基-3,5-二叔丁基苯基)丙酰胺、N,N′-[3-(4-羟基-3,5-二叔丁基苯基)丙酰]-1,6-亚己基二胺4,4′-亚甲基-二(2,6-二叔丁基酚)、2,2′-亚甲基-二(2-叔丁基-4-甲基酚)、2,4-二(4-羟基-3,5-二叔丁基苄基)-6-叔丁基酚、4,4′-亚甲基-二[2-叔丁基-4-(4-羟基-3,5-二叔丁基苄基)酚]、4-二甲基氨基甲基-2,6-二叔丁基酚、4-二丁基氨基甲基-2-甲基-6-叔丁基酚和N-二(4-羟基-3,5-二叔丁基苄基)辛胺。
特别优选的润滑油组合物是其中(B)为下式Ⅸ或Ⅹ的化合物。
[式中n为1或2,R11为氢或甲基,Y当n为1时为-O(C8~C15烷基)和当n为2时为-NH-(CH2)6-NH-基或-O-CO-(CH2)11 m s[式中n为1或2,R为氢或甲基,Y当n为1时为-O(C8~C15烷基)和当n为2时为-NH-(CH2)6-NH-基或-O-CO-(CH2)m-CO-O-基,其中m为2~8]和(C)为下述定义的式Ⅰ化合物或为2-叔丁基酚、2,6-二叔丁基酚和(对)甲醛的反应混合物的润滑油组合物,式Ⅰ中A为氢、C1~C4烷基或下式所示的基,
B为C1~C4烷基,X为C1~C4烷基或-CH2-S-R2基、-CH2CH2COOR基、-CH2N(R10)(R11)基和下式基之一,
R2为C1~C18烷基或-(CH2)2-COOR4基,R3为C1~C18烷基或
R4为C1~C18烷基和R10和R11为C1~C8烷基。
组分(B)和(C)可被直接加入基油中;或者先将(B)和(C)溶于溶剂中,然后将浓的(B)和(C)溶于少量的基油中(如果需要可以加热),然后将所得溶液与其余的油混合。另一种可行的方法是将(B)和(C)溶于溶剂中,然后将浓的的(B)和(C)的溶液与油混合。
(B)和(C)加到基油中后可提高油的抗氧化降解稳定性,和减少发动机润滑油中淤渣的形成。
润滑剂组合物还可含其它添加剂,例如磷(Ⅲ)酯、金属钝化剂、防锈剂、粘度指数改进剂、降凝剂、分散剂、表面活性剂和(或)防磨剂。
磷(Ⅲ)酯的例子有: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(壬基苯基)酯、亚磷酸三月桂酯、亚磷酸三(十八烷基)酯、二硬脂基季戊四醇二亚磷酯、亚磷酸三(2,4-二叔丁基苯基)酯、二异癸基季戊四醇二亚磷酸酯、二(2,4-二叔丁基苯基)季戊四醇二亚磷酸酯、三硬脂基山梨糖醇三亚磷酸酯、四(2,4-二叔丁基苯基)-4,4′-二亚苯基二亚膦酸酯和二(2,6-二叔丁基-4-甲基苯基)季戊四醇二亚磷酸酯。
金属钝化剂(如钝化铜的)的例子有:***、苯并***和其衍生物、甲苯***及其衍生物、2-巯基苯并噻唑、2-巯基苯并***、2,5-二巯基苯并***,2,5-二巯基苯并噻唑、5,5′-亚甲基二(苯并***)、4,5,6,7-四氢苯并***、亚水杨基丙邻二胺、水杨基氨基胍啶及其盐。
防锈剂的例子有:
a)有机酸及其酯,金属盐和酸酐,例如N-油酰次黄嘌呤、脱水山梨糖醇-油酸酯、环烷酸铅、链烯基琥珀酸酐(例如十二烯基琥珀酸酐)、链烯基琥珀酸部分酯和部分酰胺、4-壬基苯氧基乙酸。
b)含氮化合物,例如:
Ⅰ、伯、仲或叔脂族或环脂族的胺,和有机酸和无机酸的胺盐,如油溶性羧酸烷基铵。
Ⅱ、杂环化合物,例如:取代的咪唑啉和噁唑啉。
c)含磷化合物,例如磷酸部分酯或膦酸部分酯的胺盐、二烷基二硫代磷酸锌。
d)含硫化合物,例如二壬基萘磺酸钡和石油磺酸钙。
粘度指数改进剂的例子是: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/丙烯酸酯共聚物和聚醚。
降凝剂的例子是聚甲基丙烯酸酯,烷基化萘的衍生物。
分散剂/表面活性剂的例子有:聚丁烯基琥珀酰胺或聚丁烯基琥珠酰亚胺、聚丁烯基膦酸衍生物、碱式镁、钙和钡的磺酸盐和酚盐,
防磨剂的例子有:含硫和(或)磷和(或)卤素的化合物,例如硫化植物油、二烷基二硫代磷酸锌、磷酸三甲苯酯、氯化蜡烃、烷基和芳基的二硫化物和三硫化物、硫代磷酸三苯酯、二乙醇氨基甲基甲苯基***和二(2-乙基己基)氨基甲基甲苯基***。
这种润滑油还可含固体润滑材料,例如石墨或硫化钼。
兹用下面的实施例对本发明作更为详细的说明。百分率均以重量计。
实施例1
按照ASTMD-943 TOST(涡轮氧化稳定性试验)法,对根据本发明稳定化的润滑油的氧化性能进行试验。
这种试验的做法是:在有铁和铜并同时通入氧气的情况下,将60毫升水加到含有0.05%腐蚀剂抑制剂(Reocor
12)的300毫升矿物油(Mobil STOCK 305)中,然后在95℃下加热此混合物1000小时。通过测定酸值TAN(毫克KOH/克油),度量所形成的酸量。此外,还测定淤渣形成量(SLUDGE)
所用的稳定剂为:
稳定剂的总用量为油量的0.25%。稳定剂混合物的组成是变动的。所得的试验结果见表1。
表1
百分率 TOST
P-1 H-1 TAN SLUDGE
100% - 0.19 64毫克
95% 5% 0 17毫克
90% 10% 0 8毫克
75% 25% 0 26毫克
实施例2
按照实施例1中所述的方法进行试验,所用的稳定剂为
总浓度为0.25%,基于油。
表2
百分率 TOST
P-2 H-2 TAN SLUDGE
100% - >2 >1000毫克
95% 5% 0.26 219毫克
90% 10% 0.24 190毫克
实施例3
按照实施例1中所述的方法进行试验,所用的稳定剂为:
总浓度为0.25%。所得的结果见表3。
表3
百分率 TOST
P-2 H-3 TAN SLUDGE
100% - >2 >1000毫克
95% 5% 0.24 180毫克
实施例4
按照实施例1中所述的方法进行试验。所用的稳定剂为:
总浓度为0.25%。所得的试验结果见表4。
表4
百分率 TOST
P-2 H-1 TAN SLUDGE
100% - >2 1000毫克
95% 5% 0 86毫克
85% 15% 0.10 44毫克
75% 25% 0.03 75毫克
实施例5
按照实施例1所述的方法进行试验。所用的稳定剂为:
总浓度为0.25%。所得的结果见表5。
表5
百分率 TOST
P-2 H-4 TAN SLUDGE
100% - >2 >1000毫克
95% 5% 0.18 91毫克
90% 10% 0.16 161毫克
实施例6
用差示扫描量热法测定按本发明稳定化后的油的抗氧化性。做法是:首先使基油在一小铝皿中与0.025%的铁(Ⅲ)乙酰丙酮化物(作氧化催化剂)和0.55%的稳定剂混合,然后在量热器中,在10巴氧压和160℃下,对所得的混合物进行等温加热。计量放热反应开始的时间,TB(诱导时间),和放热终止的时间,TE。诱导时间越长,抗氧化性越高。所用的稳定剂除酚抗氧化剂P-1和P-2外还有:
P-3:其为160克2,6-二叔丁基酚、40克2-叔丁基酚、5.8克KOH、50毫升乙醇和24克对甲醛在80℃下的反应产物,其含有以下主要组分:
所得的试验结果见表6。
表6
稳定剂 TB(分钟) TE(分钟)
0.55%P-1 1.47 9.12
0.55%H-5 17.16 22.97
0.45%P-1
+0.10%H-5 14.02 27.71
0.55%P-2 16.08 26.07
0.55%H-5 17.16 22.97
0.45%P-2
+0.10%H-5 32.27 47.90
0.55%P-3 7.21 14.20
0.55%H-5 17.16 22.97
0.45%P-3
+0.10%H-5 50.55 67.97
+0.55%P-4 3.00 9.67
0.55%H-5 17.16 22.97
0.45%P-4
+0.10%H-5 12.02 20.37
0.55%P-5 4.46 16.44
0.55%H-5 17.16 22.97
0.45%P-5
+0.10%H-5 14.10 23.23
由此表可见,不出所料,当采用0.10%组分A和0.45%组分B的稳定剂混合物时,油的抗氧化性高于采用单一组分时。
实施例7
按实施例6中所述的方法,用差示扫描量热法进行抗氧化性试验,只是在8巴混有380ppm NOx的空气(而不是氧气)压和等温温度170℃下进行测定试验。仅测定放热开始的时间。
表7
稳定剂 TB(分钟)
0.55% P-2 11.2
0.55% H-5 <2
0.45% P-2+0.10% H-5 20.7
0.55% P-6 3.8
0.55% H-5 <2
0.45% P-6+0.10% H-5 10.8
Claims (19)
1、一种有下列组分的润滑油组合物,
(A)一种矿物油或合成油或其混合物;
(B)至少一种位阻胺;和
(C)至少一种式Ⅰ酚
式中A为氢、C1-C24烷基、C5-C12环烷基、C7-C9苯基烷基、苯基或-CH2-S-R1基或基
B为C1-C24烷基、C5-C12环烷基、C7-C9苯基烷基、苯基或-CH2-S-R1基,X为氢、C1-C18烷基或-CaH2a-Sq-R2基、-CbH2bCO-OR3基、-CbH2b-CO-N(R5)(R6)基、-CH2N(R10)
(R11)基和下式基之一,
R1为C1-C18烷基、苯基、或-(CH2)C-CO-OR4基、或-CH2CH2OR9基,R2为氢、C1-C18烷基、苯基或基
或-(CH2)c-CO-OR4或-CH2CH2OR9
这些基中的一个,其中Q为C2-C8亚烷基、C4-C6硫杂亚烷基或
-CH2CH2(OCH2CH2)d-基,R4为C1-C24烷基,R5为氢、C1-C18烷基或环已基,R6为C1-C18烷基、环已基、苯基、C1-C18取代苯基或下列基中的一个,
或R5和R6一起为可被-O-或-NH-断开的C4-C8亚烷基,R7为氢、C1-C4烷基或苯基,R8为C1-C18烷基,R9为氢、C1-C24烷基、苯基、C2-C18链烷酰或苯甲酰,R10为C1-C18烷基、环已基、苯基、C1-C18取代苯基或基
或R10和R11一起为可被-O-或-NH-断开的C4-C8亚烷基,a为0、1、2或3,b为0、1、2或3,C为1或2,d为1-5,f为2-8和q为1、2、3或4;或组分(c)为一种多酚的混合物,这种多酚的混合物是通过使至少一种下式酚
和甲醛或对甲醛反应制得的,其中C、D和E各自为C1-C24烷基、环已基或苯基;所述组合物不含芳族胺,其中(B)和(C)之和为(A)的0.05-5%(重量)。
2、根据权利要求1所述的组合物,其中(B)对(C)之重量比为1∶1-1∶100。
3、根据权利要求1所述的组合物,其中(B)和(C)之重量比为1∶3-1∶20。
5、根据权利要求44所述的组合物,其中(B)为一种含有至少一种其中R为氢的式Ⅱ基的化合物。
9、根据权利要求1所述的组合物,其中(C)为下述定义的式Ⅰ化合物,即式Ⅰ中的A为氢、C1~C8烷基、环己基、苯基或基
B为C1~C8烷基、环己基或苯基,X为C1~C8烷基或-CaH2a-S-R2基、-CbH2b-COOR3基、-CH2N(R10)R11或基
R2为C1~C12烷基、苯基或-(CH2)c-COOR4基,R3为C1~C18烷基或基
其中Q为C2~C6亚烷基、-CH2CH2SCH2CH2-基或-CH2CH2(OCH2CH2)d-基,R4为C1~C18烷基、R10和R11各自为C1~C12烷基,或R10和R11一起为1,5-亚戊基或3-氧杂-1,5-亚戊基,a为1或2,b为1或2,c为1或2和d为1~3;或者(c)为一种下式酚
和(对)甲醛的反应混合物,式中C、D和E各自为C1~C8烷基。
10、根据权利要求1所述的组合物,其中(C)为下述定义的式Ⅰ化合物,即式Ⅰ中A和B各自为C1~C4烷基、X为-CaH2a-Sq-R2基、a为0或1,q为1或2,R2为C4~C18烷基、苯基或-CH2-CO-O-R4基和R4为C1~C18烷基。
11、根据权利要求1所述的组合物,其中(C)为下述定义的式Ⅰ化合物,即式Ⅰ中A和B各自为C1~C4烷基,X为-CH2-S-R2基,R2为C8~C12烷基或-CH2-CO-OR4基和R4为C8~C18烷基。
12、根据权利要求1所述的组合物,其中(C)为下述定义的式Ⅰ化合物,即式Ⅰ中A和B各自为C1~C4烷基,X为-CbH2b-CO-OR3基,b为1或2和R3为以下诸基中的一个,
15、根据权利要求14所述的组合物,其中A、B和X为叔丁基。
17、根据权利要求16所述的组合物,其中C、D和E为叔丁基。
18、根据权利要求1所述的组合物,其中(B)为一种式Ⅸ或Ⅹ化合物
式中n为1或2,R11为氢或甲基,和Y当n为1时为-O(C8~C15烷基)和当n为2时为-NH-(CH2)b-NH-基或-O-CO(CH2)m-Co-O-基,其中m为2~8;和(C)为下述定义的式Ⅰ化合物,即其中A为氢、C1~C4烷基或基
B为C1~C4烷基,X为C1~C4烷基或-CH2-S-R2基、-CH2CH2COOR3基、-CH2N(R10)(R11)基和下式基这些其中的一个
R2为C1~C18烷基或-(CH2)2-COOR4,R3为C1~C18烷基或基
R4为C1~C18烷基和R10和R11为C1~C8烷基;或(C)为2-叔丁基酚、2,6-二叔丁基酚和(对)甲醛的反应混合物。
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US3336226A (en) * | 1965-12-28 | 1967-08-15 | Chevron Res | Phenolic pour point depressants |
US3480635A (en) * | 1966-09-28 | 1969-11-25 | Universal Oil Prod Co | N-piperidyl substituted phenylenediamines |
US3939163A (en) * | 1973-12-28 | 1976-02-17 | Ciba-Geigy Corporation | Metal salts of hindered piperidine carboxylic acids and stabilized compositions |
DE3266599D1 (en) * | 1981-02-19 | 1985-11-07 | Ciba Geigy Ag | Organic elastomers and mineral and synthetic lubricating oils containing phenolmercaptocarboxylic esters as stabilizers |
US4362887A (en) * | 1981-04-10 | 1982-12-07 | The Goodyear Tire & Rubber Company | Synergistic antioxidant mixtures |
US4582943A (en) * | 1983-12-23 | 1986-04-15 | Ciba-Geigy Corporation | Stabilization of polyalkylene glycols |
US4607104A (en) * | 1985-07-11 | 1986-08-19 | Uniroyal Chemical Company, Inc. | Process for the production of 2,2,6,6-tetraalkyl-4-piperidylamines |
CA1248516A (en) * | 1985-07-15 | 1989-01-10 | Stephen C. Cohen | Lubricating oil compositions containing novel combination of stabilizers |
DE3671241D1 (de) * | 1985-11-13 | 1990-06-21 | Ciba Geigy Ag | Substituierte phenole als stabilisatoren. |
EP0273013B2 (de) * | 1986-12-24 | 1996-07-24 | Ciba-Geigy Ag | Substituierte Phenole als Stabilisatoren |
US4836943A (en) * | 1987-07-15 | 1989-06-06 | Texaco Inc. | Anti-oxidant system |
DE58901932D1 (de) * | 1988-06-09 | 1992-09-03 | Ciba Geigy Ag | Schmieroelzusammensetzung. |
US5073278A (en) * | 1988-07-18 | 1991-12-17 | Ciba-Geigy Corporation | Lubricant composition |
-
1990
- 1990-07-04 EP EP90112762A patent/EP0406826B1/de not_active Expired - Lifetime
- 1990-07-04 DE DE9090112762T patent/DE59002284D1/de not_active Expired - Lifetime
- 1990-07-05 BR BR909003187A patent/BR9003187A/pt not_active Application Discontinuation
- 1990-07-05 CA CA002020558A patent/CA2020558C/en not_active Expired - Lifetime
- 1990-07-05 DD DD90342534A patent/DD297443A5/de not_active IP Right Cessation
- 1990-07-06 JP JP2179385A patent/JP2943004B2/ja not_active Expired - Lifetime
- 1990-07-06 ZA ZA905305A patent/ZA905305B/xx unknown
- 1990-07-07 KR KR1019900010358A patent/KR0151400B1/ko not_active IP Right Cessation
- 1990-07-07 CN CN90103183A patent/CN1028243C/zh not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
EP0406826B1 (de) | 1993-08-11 |
KR910003079A (ko) | 1991-02-26 |
JPH0345696A (ja) | 1991-02-27 |
DE59002284D1 (de) | 1993-09-16 |
KR0151400B1 (ko) | 1998-10-01 |
CA2020558A1 (en) | 1991-01-08 |
ZA905305B (en) | 1991-05-29 |
CN1048560A (zh) | 1991-01-16 |
BR9003187A (pt) | 1991-08-27 |
JP2943004B2 (ja) | 1999-08-30 |
DD297443A5 (de) | 1992-01-09 |
CA2020558C (en) | 2001-11-06 |
EP0406826A1 (de) | 1991-01-09 |
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