CN115960650A - Lubricating oil composition for air compressor and preparation method thereof - Google Patents

Lubricating oil composition for air compressor and preparation method thereof Download PDF

Info

Publication number
CN115960650A
CN115960650A CN202111186803.7A CN202111186803A CN115960650A CN 115960650 A CN115960650 A CN 115960650A CN 202111186803 A CN202111186803 A CN 202111186803A CN 115960650 A CN115960650 A CN 115960650A
Authority
CN
China
Prior art keywords
group
straight
independently selected
groups
branched alkyl
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.)
Granted
Application number
CN202111186803.7A
Other languages
Chinese (zh)
Other versions
CN115960650B (en
Inventor
景一川
王玉睿涵
刘辉
陈晓伟
闫欢
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sinopec Research Institute of Petroleum Processing
China Petroleum and Chemical Corp
Original Assignee
Sinopec Research Institute of Petroleum Processing
China Petroleum and Chemical Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sinopec Research Institute of Petroleum Processing , China Petroleum and Chemical Corp filed Critical Sinopec Research Institute of Petroleum Processing
Priority to CN202111186803.7A priority Critical patent/CN115960650B/en
Publication of CN115960650A publication Critical patent/CN115960650A/en
Application granted granted Critical
Publication of CN115960650B publication Critical patent/CN115960650B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Landscapes

  • Lubricants (AREA)

Abstract

The invention provides an air compressor lubricating oil composition, which comprises, by mass, 0.1-10% of an organic boron compound, 0.01-5% of an antioxidant, 0.01-5% of an extreme pressure antiwear agent, 0.001-1% of a defoaming agent and a main amount of ester lubricating base oil, wherein the organic boron compound has a structure shown in formula (I):

Description

空气压缩机润滑油组合物及其制备方法Air compressor lubricating oil composition and preparation method thereof

技术领域Technical Field

本发明涉及一种润滑油,特别涉及一种空气压缩机润滑油组合物及其制备方法。The invention relates to a lubricating oil, in particular to an air compressor lubricating oil composition and a preparation method thereof.

背景技术Background Art

空气压缩机是一种通用性机械设备,能提供动力和工艺气体,在行业中应用广泛。随着空气压缩机技术的发展,对空气压缩机润滑油的性能提出了更高的要求。对于循环使用的空气压缩机润滑油,需具有更强的抗高温氧化能力和极压抗磨性能。相对于矿物空气压缩机润滑油而言,合成空气压缩机油具有高低温性能好、使用寿命长、性价比高、可提高压缩机运行安全系数、对环境污染较少等优点,能更好地适应新型压缩机的使用和需要,但同样存在换油周期短、抗高温氧化能力欠佳等问题。Air compressor is a general-purpose mechanical equipment that can provide power and process gas and is widely used in the industry. With the development of air compressor technology, higher requirements are placed on the performance of air compressor lubricants. For recycled air compressor lubricants, it is necessary to have stronger resistance to high temperature oxidation and extreme pressure and anti-wear properties. Compared with mineral air compressor lubricants, synthetic air compressor oils have the advantages of good high and low temperature performance, long service life, high cost performance, improved compressor operation safety factor, less environmental pollution, etc., and can better adapt to the use and needs of new compressors, but there are also problems such as short oil change cycle and poor resistance to high temperature oxidation.

在空气压缩机润滑油中,所使用的抗氧剂主要包括酚型、胺型、酚酯型、硫代酯型、亚磷酸酯型等等,其中受阻酚型抗氧剂的使用较为广泛。例如CN 113088368、CN 92102699、CN 99811367、USP 5124057、USP 6207623、USP 6410490等均采用受阻酚型抗氧剂为其抗氧剂组分之一,但采用一般的受阻酚型抗氧剂难于满足长寿命的要求。因此现有技术仍需要长寿命的并具有优异氧化安定性能和抗磨性能的空气压缩机润滑油组合物。In air compressor lubricating oil, the antioxidants used mainly include phenol type, amine type, phenol ester type, thioester type, phosphite type, etc., among which hindered phenol type antioxidants are widely used. For example, CN 113088368, CN 92102699, CN 99811367, USP 5124057, USP 6207623, USP 6410490, etc. all use hindered phenol type antioxidants as one of their antioxidant components, but it is difficult to meet the requirements of long life by using general hindered phenol type antioxidants. Therefore, the prior art still needs an air compressor lubricating oil composition with long life and excellent oxidation stability and anti-wear performance.

发明内容Summary of the invention

本发明提出了一种空气压缩机润滑油组合物及其制备方法,所述空气压缩机润滑油组合物具有优异的高温抗氧化性能和抗磨性能。The invention provides an air compressor lubricating oil composition and a preparation method thereof. The air compressor lubricating oil composition has excellent high-temperature anti-oxidation performance and anti-wear performance.

本发明的空气压缩机润滑油组合物,以质量百分比计,包括0.1%~10%的有机硼化合物、0.01%~5%的抗氧剂、0.01%~5%的极压抗磨剂、0.001%~1%的消泡剂和主要量的酯类润滑基础油,其中所述有机硼化合物的结构如式(I)所示:The air compressor lubricating oil composition of the present invention comprises, by mass percentage, 0.1% to 10% of an organic boron compound, 0.01% to 5% of an antioxidant, 0.01% to 5% of an extreme pressure anti-wear agent, 0.001% to 1% of a defoaming agent, and a major amount of an ester lubricating base oil, wherein the structure of the organic boron compound is as shown in formula (I):

Figure BDA0003299587390000021
Figure BDA0003299587390000021

在式(I)中,存在a个重复单元L和b个含硼基团,a为1~10之间的整数(优选1~5之间的整数),b为1~5之间的整数(优选1~3之间的整数),a个L基团彼此相同或不同,各自独立地选自式(II)所示的基团;In formula (I), there are a repeating unit L and b boron-containing groups, a is an integer between 1 and 10 (preferably an integer between 1 and 5), b is an integer between 1 and 5 (preferably an integer between 1 and 3), and a L groups are the same or different and are independently selected from the group represented by formula (II);

Figure BDA0003299587390000022
Figure BDA0003299587390000022

在式(II)中,HO与苯环键合(HO优选位于苯环上R1所在链的间位);y个R基团与苯环键合;y选自0~4之间的整数(优选1~3之间的整数);R基团各自独立地选自H和C1-20直链或支链烷基(优选各自独立地选自H和C1-4直链或支链烷基,更优选叔丁基);n为1~10之间的整数(优选1~3之间的整数);R1各自独立地选自单键和C1-20直链或支链的亚烷基(优选选自单键和C1-4直链或支链的亚烷基);n个重复单元中的R2彼此相同或不同,各自独立地选自单键和C1-20直链或支链的亚烷基(优选各自独立地选自单键和C1-4直链或支链的亚烷基);R3选自H和C1-20直链或支链烷基(优选选自H和C1-4直链或支链烷基);n个重复单元中的A基团彼此相同或不同,各自独立地选自单键、

Figure BDA0003299587390000023
式(III)所示的基团和式(IV)所示的基团,In formula (II), HO is bonded to the benzene ring (HO is preferably located at the meta position of the chain where R 1 is located on the benzene ring); y R groups are bonded to the benzene ring; y is selected from an integer between 0 and 4 (preferably an integer between 1 and 3); the R groups are each independently selected from H and C 1-20 straight or branched alkyl (preferably each independently selected from H and C 1-4 straight or branched alkyl, more preferably tert-butyl); n is an integer between 1 and 10 (preferably an integer between 1 and 3); R 1 is each independently selected from a single bond and a C 1-20 straight or branched alkylene (preferably selected from a single bond and a C 1-4 straight or branched alkylene); R 2 in the n repeating units are the same or different from each other and are each independently selected from a single bond and a C 1-20 straight or branched alkylene (preferably each independently selected from a single bond and a C 1-4 straight or branched alkylene); R 3 is selected from H and a C 1-20 straight or branched alkyl (preferably selected from H and C 1-4 straight or branched alkyl groups); the A groups in the n repeating units are the same or different from each other and are independently selected from a single bond,
Figure BDA0003299587390000023
The group represented by formula (III) and the group represented by formula (IV),

Figure BDA0003299587390000031
Figure BDA0003299587390000031

所述R4基团各自独立地选自H和C1-20直链或支链烷基(优选选自H和C1-4直链或支链烷基);The R4 groups are each independently selected from H and C1-20 straight or branched alkyl (preferably selected from H and C1-4 straight or branched alkyl);

m为0~10之间的整数(优选1~5之间的整数);m is an integer between 0 and 10 (preferably an integer between 1 and 5);

所述的R5基团各自独立地选自3价的C1-20直链或支链烷基(优选各自独立地选自3价的C1-4直链或支链烷基);The R 5 groups are each independently selected from a trivalent C 1-20 straight chain or branched chain alkyl group (preferably each independently selected from a trivalent C 1-4 straight chain or branched chain alkyl group);

各个G2基团各自独立地选自与其所在L基团之外的其它L基团中存在的G4基团键合的结合端、C1-10直链或支链的烷基、-R6G3、H;各个G3基团各自独立地选自-OG1、C1-10直链或支链的烷基、H(优选各自独立地选自-OG1、C1-4直链或支链的烷基、OH、H);Each G2 group is independently selected from the group bonded to the G4 group present in the other L group other than the L group in which it is located, a C1-10 straight or branched alkyl group, -R6G3 , and H; each G3 group is independently selected from -OG1 , a C1-10 straight or branched alkyl group, and H (preferably, independently selected from -OG1 , a C1-4 straight or branched alkyl group, OH, and H);

所述的R6基团选自C1-20直链或支链的亚烷基(优选各自独立地选自C1-4直链或支链的亚烷基);The R 6 groups are selected from C 1-20 straight or branched alkylene groups (preferably each independently selected from C 1-4 straight or branched alkylene groups);

G1基团选自与所述含硼基团键合的结合端、H;The G1 group is selected from the binding end bonded to the boron-containing group, H;

G4基团选自与其所在L基团之外的其它L基团中存在的G2基团键合的结合端、H;The G4 group is selected from the binding end bonded to the G2 group present in other L groups other than the L group in which it is located, H;

在a个L基团中,至少存在一个A基团选自式(III)所示的基团,至少存在一个G1基团选自与含硼基团中的硼元素键合的结合端;Among a L groups, at least one A group is selected from the group represented by formula (III), and at least one G1 group is selected from the binding end bonded to the boron element in the boron-containing group;

b个所述含硼基团中的各个A’基团各自独立地选自与L基团中存在的G1基团键合的结合端、式(V)所示的基团、-OR’,所述的R’基团为H或C1-20直链或支链的烷基(优选为H或C1-4直链或支链的烷基);Each A' group in the b boron-containing groups is independently selected from the binding end bonded to the G1 group present in the L group, the group represented by formula (V), -OR', and the R' group is H or a C 1-20 straight or branched alkyl group (preferably H or a C 1-4 straight or branched alkyl group);

Figure BDA0003299587390000041
Figure BDA0003299587390000041

在式(V)中,m为0~10之间的整数(优选1~5之间的整数);In formula (V), m is an integer between 0 and 10 (preferably an integer between 1 and 5);

所述的R0基团各自独立地选自C1-10直链或支链烷基、-R6G5、H(优选各自独立地选自C1-4直链或支链烷基、-R6G5、H);The R 0 groups are each independently selected from C 1-10 straight or branched alkyl, -R 6 G 5 , H (preferably each independently selected from C 1-4 straight or branched alkyl, -R 6 G 5 , H);

所述的R5基团各自独立地选自3价的C1-20直链或支链烷基(优选各自独立地选自3价的C1-4直链或支链烷基);The R 5 groups are each independently selected from a trivalent C 1-20 straight chain or branched chain alkyl group (preferably each independently selected from a trivalent C 1-4 straight chain or branched chain alkyl group);

G6基团选自-R6G5、C1-4直链或支链的烷基、H;The G6 group is selected from -R6G5 , C1-4 straight or branched alkyl, H;

所述的R6基团选自C1-20直链或支链的亚烷基(优选各自独立地选自C1-4直链或支链的亚烷基);The R 6 groups are selected from C 1-20 straight or branched alkylene groups (preferably each independently selected from C 1-4 straight or branched alkylene groups);

各个G5基团各自独立地选自-OG1、C1-4直链或支链的烷基、OH、H,其中的G1基团选自与所述含硼基团中的硼元素键合的结合端、C1-4直链或支链的烷基、H;Each G 5 group is independently selected from -OG 1 , C 1-4 straight or branched alkyl, OH, H, wherein the G 1 group is selected from the binding end bonded to the boron element in the boron-containing group, C 1-4 straight or branched alkyl, H;

在式(V)所示的基团中,至少存在一个G1基团选自与含硼基团中的硼元素键合的结合端;In the group represented by formula (V), there is at least one G1 group selected from the binding end bonded to the boron element in the boron-containing group;

在b个所述含硼基团中,至少存在一个A’基团选自与L基团中存在的G1基团键合的结合端;Among the b said boron-containing groups, at least one A' group is selected from the binding end bonded to the G1 group present in the L group;

所述有机硼化合物中的各个基团符合成键规则。Each group in the organic boron compound complies with the bonding rules.

根据本发明,式(III)或式(IV)中的两个与式(II)键合的结合端可以以任意方式与式(II)中的基团键合,例如可以沿一个方向与式(II)键合,也可以沿相反方向与式(II)键合。According to the present invention, the two binding ends in formula (III) or formula (IV) that are bonded to formula (II) can be bonded to the groups in formula (II) in any manner, for example, they can be bonded to formula (II) in one direction or in the opposite direction.

根据本发明,可以举出的所述有机硼化合物的例子包括以下结构化合物中的一种或多种:According to the present invention, examples of the organoboron compound include one or more of the following structural compounds:

Figure BDA0003299587390000051
Figure BDA0003299587390000051

Figure BDA0003299587390000061
Figure BDA0003299587390000061

其中的R基团为H或C1-C20的直链或支链烷基。The R group is H or a C 1 -C 20 straight or branched chain alkyl group.

根据本发明,所述有机硼化合物的制备方法包括以下步骤:According to the present invention, the method for preparing the organic boron compound comprises the following steps:

(1)使式(X)所示的化合物与过氧化物反应;(1) reacting a compound represented by formula (X) with a peroxide;

Figure BDA0003299587390000062
Figure BDA0003299587390000062

在式(X)中,HO与苯环键合(HO优选位于苯环上R1所在链的间位);y个R基团与苯环键合;y选自0~4之间的整数(优选1~3之间的整数);R基团各自独立地选自H和C1-20直链或支链烷基(优选各自独立地选自H和C1-4直链或支链烷基,更优选选自叔丁基);n为1~10之间的整数(优选1~3之间的整数);R1各自独立地选自单键和C1-20直链或支链的亚烷基(优选选自单键和C1-4直链或支链的亚烷基);n个重复单元中的R2彼此相同或不同,各自独立地选自单键和C1-20直链或支链的亚烷基(优选各自独立地选自单键和C1-4直链或支链的亚烷基);R3选自H和C1-20直链或支链烷基(优选选自H和C1-4直链或支链烷基);n个重复单元中的A”彼此相同或不同,各自独立地选自单键、

Figure BDA0003299587390000063
Figure BDA0003299587390000071
其中所述的R4基团各自独立地选自H和C1-20直链或支链烷基(优选选自H和C1-4直链或支链烷基);在式(X)中至少存在一个A”为
Figure BDA0003299587390000072
In formula (X), HO is bonded to the benzene ring (HO is preferably located at the meta position of the chain where R 1 is located on the benzene ring); y R groups are bonded to the benzene ring; y is selected from an integer between 0 and 4 (preferably an integer between 1 and 3); the R groups are each independently selected from H and C 1-20 straight or branched alkyl (preferably each independently selected from H and C 1-4 straight or branched alkyl, more preferably selected from tert-butyl); n is an integer between 1 and 10 (preferably an integer between 1 and 3); R 1 is each independently selected from a single bond and a C 1-20 straight or branched alkylene (preferably selected from a single bond and a C 1-4 straight or branched alkylene); R 2 in the n repeating units are the same or different from each other and are each independently selected from a single bond and a C 1-20 straight or branched alkylene (preferably each independently selected from a single bond and a C 1-4 straight or branched alkylene); R 3 is selected from H and C 1-20 straight or branched chain alkyl groups (preferably selected from H and C 1-4 straight or branched chain alkyl groups); A" in the n repeating units are the same or different from each other and are independently selected from single bonds,
Figure BDA0003299587390000063
Figure BDA0003299587390000071
wherein the R4 groups are independently selected from H and C1-20 straight chain or branched alkyl (preferably selected from H and C1-4 straight chain or branched alkyl); in formula (X), at least one A" is
Figure BDA0003299587390000072

(2)使步骤(1)的反应产物与式(Y)所示的化合物反应;(2) reacting the reaction product of step (1) with a compound represented by formula (Y);

Figure BDA0003299587390000073
Figure BDA0003299587390000073

在式(Y)中,m为0~10之间的整数(优选1~5之间的整数);In formula (Y), m is an integer between 0 and 10 (preferably an integer between 1 and 5);

所述的R0’基团各自独立地选自C1-10直链或支链烷基、-R6OH、H(优选各自独立地选自C1-4直链或支链烷基、-R6OH、H);所述的R5基团各自独立地选自3价的C1-20直链或支链烷基(优选各自独立地选自3价的C1-4直链或支链烷基);各个G5’基团各自独立地选自C1-4直链或支链的烷基、OH、H;所述的G6’基团选自C1-10直链或支链的烷基、-R6OH、H;所述的R6基团各自独立地选自C1-20直链或支链的亚烷基(优选各自独立地选自C1-4直链或支链的亚烷基);The R 0 'groups are each independently selected from C 1-10 straight or branched alkyl, -R 6 OH, H (preferably each independently selected from C 1-4 straight or branched alkyl, -R 6 OH, H); the R 5 groups are each independently selected from trivalent C 1-20 straight or branched alkyl (preferably each independently selected from trivalent C 1-4 straight or branched alkyl); each G 5 'group is each independently selected from C 1-4 straight or branched alkyl, OH, H; the G 6 'group is selected from C 1-10 straight or branched alkyl, -R 6 OH, H; the R 6 groups are each independently selected from C 1-20 straight or branched alkylene (preferably each independently selected from C 1-4 straight or branched alkylene);

在式(Y)中,至少存在一个G5’基团选自OH或者至少一个G6’基团或R0’基团选自-R6OH,并且至少存在一个R0’基团或G6’基团为H;In formula (Y), there is at least one G 5 'group selected from OH or at least one G 6 'group or R 0 'group selected from -R 6 OH, and at least one R 0 'group or G 6 'group is H;

(3)使步骤(2)的反应产物与无机硼化合物反应,收集产物。(3) reacting the reaction product of step (2) with an inorganic boron compound and collecting the product.

根据本发明,在步骤(1)中,式(X)所示的化合物可以选自腰果酚、烷基化腰果酚,所述烷基化腰果酚可以通过腰果酚与烷基化剂反应得到,例如可以通过腰果酚与叔丁基氯反应得到叔丁基化腰果酚。According to the present invention, in step (1), the compound represented by formula (X) can be selected from cardanol and alkylated cardanol. The alkylated cardanol can be obtained by reacting cardanol with an alkylating agent, for example, tert-butyl cardanol can be obtained by reacting cardanol with tert-butyl chloride.

根据本发明,在步骤(1)中,所述过氧化物优选双氧水、过氧甲酸、过氧乙酸、过氧磺酸、间氯过氧苯甲酸、叔丁基过氧化氢、过氧乙酸叔丁酯、过氧化甲基乙基酮、过氧化二苯甲酰和过氧化环己酮中的一种或多种,更优选双氧水、过氧化甲酸、过氧乙酸和过氧磺酸中的一种或多种。According to the present invention, in step (1), the peroxide is preferably one or more of hydrogen peroxide, performic acid, peracetic acid, persulfonic acid, m-chloroperbenzoic acid, tert-butyl hydroperoxide, tert-butyl peracetate, methyl ethyl ketone peroxide, dibenzoyl peroxide and cyclohexanone peroxide, more preferably one or more of hydrogen peroxide, formic acid peroxide, peracetic acid and persulfonic acid.

根据本发明,在步骤(2)中,式(Y)所示的化合物可以选自脂肪胺、多烯多胺、一个或多个羟基取代的脂肪胺、一个或多个羟基取代的多烯多胺中的一种或多种,例如可以选用乙醇胺、二乙醇胺、羟乙基乙二胺(即N-(2-羟乙基)乙二胺)、二乙烯三胺、三乙烯四胺、四乙烯五胺和五乙烯六胺中的一种或多种。According to the present invention, in step (2), the compound represented by formula (Y) can be selected from one or more of aliphatic amines, polyene polyamines, aliphatic amines substituted with one or more hydroxy groups, polyene polyamines substituted with one or more hydroxy groups, for example, one or more of ethanolamine, diethanolamine, hydroxyethylethylenediamine (i.e., N-(2-hydroxyethyl)ethylenediamine), diethylenetriamine, triethylenetetramine, tetraethylenepentamine and pentaethylenehexamine can be selected.

根据本发明,在步骤(3)中,所述无机硼化合物优选选自硼酸、氧化硼和硼酸半酯中的一种或多种,所述硼酸半酯可以选用硼酸单烷基酯、硼酸二烷基酯,其中的烷基为C1-C20的直链或支链烷基。According to the present invention, in step (3), the inorganic boron compound is preferably selected from one or more of boric acid, boric oxide and boric acid half ester. The boric acid half ester can be selected from monoalkyl borate or dialkyl borate, wherein the alkyl group is a C 1 -C 20 straight chain or branched chain alkyl group.

根据本发明,式(X)所示的化合物与过氧化物、式(Y)所示的化合物、无机硼化合物之间的当量比优选为1:0.5~10:0.5~10:0.5~5,更优选为1:2~3:2~3:1~2。According to the present invention, the equivalent ratio of the compound represented by formula (X) to the peroxide, the compound represented by formula (Y), and the inorganic boron compound is preferably 1:0.5-10:0.5-10:0.5-5, and more preferably 1:2-3:2-3:1-2.

根据本发明,步骤(1)的反应温度优选为0~100℃,更优选为20~80℃;步骤(2)的反应温度优选为50~150℃,更优选为60~100℃;步骤(3)的反应温度优选为80~200℃,更优选为110~150℃。According to the present invention, the reaction temperature of step (1) is preferably 0-100°C, more preferably 20-80°C; the reaction temperature of step (2) is preferably 50-150°C, more preferably 60-100°C; the reaction temperature of step (3) is preferably 80-200°C, more preferably 110-150°C.

根据本发明,步骤(1)、步骤(2)、步骤(3)的反应时间通常越长越好,一般来说,步骤(1)的反应时间优选为1~10h,更优选为3~5h;步骤(2)的反应时间优选为1~10h,更优选为2~4h;步骤(3)的反应时间优选为1~10h,更优选为3~5h。According to the present invention, the reaction time of step (1), step (2) and step (3) is usually as long as possible. Generally speaking, the reaction time of step (1) is preferably 1 to 10 hours, more preferably 3 to 5 hours; the reaction time of step (2) is preferably 1 to 10 hours, more preferably 2 to 4 hours; the reaction time of step (3) is preferably 1 to 10 hours, more preferably 3 to 5 hours.

根据本发明,在步骤(3)的反应中,还可以加入式(Y)所示的化合物,所述式(Y)所示的化合物与无机硼化合物之间的当量比优选为1:0.5~5,更优选为1:0.8~3。According to the present invention, in the reaction of step (3), a compound represented by formula (Y) may also be added, and the equivalent ratio between the compound represented by formula (Y) and the inorganic boron compound is preferably 1:0.5-5, more preferably 1:0.8-3.

根据本发明,所述反应步骤(1)、(2)或(3)可以在稀释剂和/或溶剂的存在下进行,也可以不使用稀释剂和/或溶剂。According to the present invention, the reaction steps (1), (2) or (3) may be carried out in the presence of a diluent and/or a solvent, or may be carried out without using a diluent and/or a solvent.

根据本发明,所述稀释剂可以选用API I、II、III、IV和V类基础油中的一种或多种,常见的商品或牌号包括150SN、200SN、350SN、500SN、650SN、150BS、HVI-100、HVI-150、HVI-200、HVI-350、HVI-400、HVI-500、HVI-150BS、PAO4、PAO6、PAO8、PAO10、烷基苯、烷基萘等。According to the present invention, the diluent can be selected from one or more of API I, II, III, IV and V base oils. Common products or brands include 150SN, 200SN, 350SN, 500SN, 650SN, 150BS, HVI-100, HVI-150, HVI-200, HVI-350, HVI-400, HVI-500, HVI-150BS, PAO4, PAO6, PAO8, PAO10, alkylbenzene, alkylnaphthalene, etc.

根据本发明,所述溶剂可以选用C6-20芳香烃(比如苯、甲苯、二甲苯和异丙苯)、C6-10烷烃(比如正己烷、环己烷和石油醚)、溶剂汽油等。这些溶剂可以仅使用一种,也可以两种或多种组合使用。所述溶剂可在反应结束后,使用本领域技术人员公知的方式,例如在常压或减压条件下蒸除溶剂。According to the present invention, the solvent can be selected from C 6-20 aromatic hydrocarbons (such as benzene, toluene, xylene and isopropylbenzene), C 6-10 alkanes (such as n-hexane, cyclohexane and petroleum ether), solvent gasoline, etc. These solvents can be used alone or in combination of two or more. After the reaction is completed, the solvent can be removed by a method known to those skilled in the art, such as distilling the solvent under normal pressure or reduced pressure.

根据本发明的一个特别实施方式,所述稀释剂和/或溶剂可以在所述反应步骤的任何阶段按照本领域的常规用量加入,并没有特别的限定。According to a particular embodiment of the present invention, the diluent and/or solvent may be added at any stage of the reaction step according to conventional amounts in the art, without particular limitation.

根据本发明,显然的是,所述反应步骤一般在惰性气体气氛的保护下进行。作为所述惰性气体,比如可以举出氮气和氩气等,并没有特别的限定。According to the present invention, it is obvious that the reaction step is generally carried out under the protection of an inert gas atmosphere. Examples of the inert gas include nitrogen and argon, etc., without particular limitation.

根据本发明,在步骤(3)中,可以加入促使反应完全的促进剂,常见的促进剂包括水、乙醇、丙醇、丁醇、氨水等。如加入促进剂,可在反应结束后,使用本领域技术人员公知的方式,例如在常压或减压条件下蒸除。According to the present invention, in step (3), a promoter may be added to promote the completion of the reaction. Common promoters include water, ethanol, propanol, butanol, ammonia, etc. If a promoter is added, it can be removed after the reaction by a method known to those skilled in the art, such as distillation under normal pressure or reduced pressure.

根据本发明,通过前述的有机硼化合物的制备方法,作为反应产物,可以制造出单一的一种有机硼化合物,也可以制造出由多种有机硼化合物构成的混合物,或者由一种或多种所述有机硼化合物与前述稀释剂(如果使用的话)构成的混合物。这些反应产物都是本发明所预期的,其存在形式的不同并不影响本发明效果的实现。因此,本说明书上下文中不加区分地将这些反应产物均统称为有机硼化合物。鉴于此,根据本发明,并不存在进一步纯化该反应产物,或者从该反应产物中进一步分离出某一特定结构的有机硼化合物的绝对必要性。当然,该纯化或分离对于本发明预期效果的进一步提升而言是优选的,但对于本发明并不必需。虽然如此,作为所述纯化或分离方法,比如可以举出通过柱层析方法或制备色谱等方法对所述反应产物进行纯化或分离等。According to the present invention, by the aforementioned method for preparing an organoboron compound, as a reaction product, a single organoboron compound can be produced, a mixture consisting of a plurality of organoboron compounds can also be produced, or a mixture consisting of one or more of the organoboron compounds and the aforementioned diluent (if used). These reaction products are all expected by the present invention, and the difference in their existence forms does not affect the realization of the effect of the present invention. Therefore, in the context of this specification, these reaction products are all collectively referred to as organoboron compounds without distinction. In view of this, according to the present invention, there is no absolute necessity to further purify the reaction product, or to further separate an organoboron compound of a certain structure from the reaction product. Of course, the purification or separation is preferred for further improvement of the expected effect of the present invention, but is not necessary for the present invention. Nevertheless, as the purification or separation method, for example, the reaction product can be purified or separated by a column chromatography method or a preparative chromatography method.

本发明的有机硼化合物同时具有优良的抗氧化性能和抗磨减摩性能。The organic boron compound of the invention has excellent antioxidant performance and anti-wear and friction-reducing performance.

根据本发明,所述抗氧剂优选选自酚型抗氧剂,例如可以选用2,6二叔丁基对甲酚、2,6-二叔丁基混合酯、4,4-亚甲基双(2,6-二叔丁基酚)和2,6-二叔丁基-α二甲氨基对甲酚中的一种或多种,常见的商品牌号包括T501、T512、BHT等。According to the present invention, the antioxidant is preferably selected from phenolic antioxidants, for example, one or more of 2,6-di-tert-butyl-p-cresol, 2,6-di-tert-butyl mixed esters, 4,4-methylenebis(2,6-di-tert-butylphenol) and 2,6-di-tert-butyl-α-dimethylamino-p-cresol can be selected. Common trade names include T501, T512, BHT, etc.

根据本发明,所述极压抗磨剂优选选自硫磷酸含氮衍生物、磷酸酯、亚磷酸酯、硫代磷酸胺盐、硫化烯烃和二烷基二硫代氨基甲酸盐中的一种或多种,例如可以选用硫磷酸含氮衍生物、亚磷酸二正丁酯、磷酸三甲酚酯、磷酸三乙酯、硫代磷酸胺盐、硫化异丁烯和二丁基二硫代氨基甲酸锌中的一种或多种,常见的商品牌号包括T304、T305、T306、T307、T321等。According to the present invention, the extreme pressure anti-wear agent is preferably selected from one or more of thiophosphoric acid nitrogen-containing derivatives, phosphates, phosphites, thiophosphoric acid amine salts, sulfided olefins and dialkyl dithiocarbamates. For example, one or more of thiophosphoric acid nitrogen-containing derivatives, di-n-butyl phosphite, tricresyl phosphate, triethyl phosphate, thiophosphoric acid amine salts, sulfided isobutylene and zinc dibutyl dithiocarbamate can be selected. Common trade names include T304, T305, T306, T307, T321, etc.

根据本发明,所述消泡剂优选选自丙烯酸与醚的共聚物、甲基硅油和乙基硅油中的一种或多种,常见的商品牌号包括T911、T912、T901等。According to the present invention, the defoaming agent is preferably selected from one or more of a copolymer of acrylic acid and ether, methyl silicone oil and ethyl silicone oil. Common trade names include T911, T912, T901 and the like.

根据本发明,所述酯类润滑基础油优选双酯类润滑基础油,例如可以选用癸二酸二异辛酯、己二酸二异辛酯等。According to the present invention, the ester lubricating base oil is preferably a diester lubricating base oil, for example, diisooctyl sebacate, diisooctyl adipate, etc. may be selected.

根据本发明,优选地,所述空气压缩机润滑油组合物,以质量百分比计,包括0.2%~5%的有机硼化合物、0.01%~3%的抗氧剂、0.01%~3%的极压抗磨剂、0.001%~0.5%的消泡剂和主要量的酯类润滑基础油。According to the present invention, preferably, the air compressor lubricating oil composition comprises, by mass percentage, 0.2% to 5% of an organic boron compound, 0.01% to 3% of an antioxidant, 0.01% to 3% of an extreme pressure anti-wear agent, 0.001% to 0.5% of a defoaming agent and a major amount of an ester lubricating base oil.

本发明的空气压缩机润滑油组合物的制备方法,包括将前述所述的空气压缩机润滑油组合物中的添加剂和润滑基础油混合的步骤。所述混合的温度优选为40℃~90℃,混合时间优选为1h~6h。The method for preparing the air compressor lubricant composition of the present invention comprises the step of mixing the additives in the air compressor lubricant composition and the lubricant base oil. The mixing temperature is preferably 40° C. to 90° C., and the mixing time is preferably 1 hour to 6 hours.

本发明的空气压缩机润滑油组合物具有优异的高温抗氧化性能和抗磨性能,能满足长寿命空气压缩机润滑油组合物的要求。The air compressor lubricating oil composition of the present invention has excellent high-temperature anti-oxidation performance and anti-wear performance, and can meet the requirements of a long-life air compressor lubricating oil composition.

具体实施方式DETAILED DESCRIPTION

在本说明书中,在基团的定义中有时使用术语“单键”。所谓“单键”,指的是该基团不存在。举例而言,假定结构式-CH2-A-CH3,其中基团A被定义为选自单键和甲基。鉴于此,若A是单键,则代表该基团A不存在,此时所述结构式即被相应简化为-CH2-CH3In this specification, the term "single bond" is sometimes used in the definition of a group. The so-called "single bond" means that the group does not exist. For example, assuming the structural formula -CH 2 -A-CH 3 , where the group A is defined as being selected from a single bond and a methyl group. In view of this, if A is a single bond, it means that the group A does not exist, and the structural formula is correspondingly simplified to -CH 2 -CH 3 .

在本说明书的上下文中,表达方式“数字+价+基团”或其类似用语指的是从该基团所对应的基础结构(比如链、环或其组合等)上除去该数字所代表的数量的氢原子后获得的基团,优选指的是从该结构所含的碳原子(优选饱和碳原子和/或非同一个碳原子)上除去该数字所代表的数量的氢原子后获得的基团。举例而言,“3价直链或支链烷基”指的是从直链或支链烷烃(即该直链或支链烷基所对应的基础链)上除去3个氢原子而获得的基团。In the context of this specification, the expression "number + valence + group" or similar expressions refers to a group obtained by removing the number of hydrogen atoms represented by the number from the basic structure (such as a chain, a ring or a combination thereof) corresponding to the group, preferably refers to a group obtained by removing the number of hydrogen atoms represented by the number from the carbon atoms (preferably saturated carbon atoms and/or non-identical carbon atoms) contained in the structure. For example, "trivalent straight or branched alkyl" refers to a group obtained by removing 3 hydrogen atoms from a straight or branched alkane (i.e., the basic chain corresponding to the straight or branched alkyl).

下面通过实施例对本发明做进一步说明,但并非构成对本发明的限制。The present invention is further described below by way of examples, but they are not intended to limit the present invention.

所用主要原料如下:The main raw materials used are as follows:

腰果酚,上海物竞化工科技有限公司,工业品Cardanol, Shanghai Wujing Chemical Technology Co., Ltd., industrial products

氯化锌,浓硫酸,双氧水(30%),甲酸,硼酸,二乙醇胺,二乙烯三胺,乙醇胺,N-(2-羟乙基)乙二胺,叔丁基氯,十六醇,均购自国药集团化学试剂有限公司,分析纯。Zinc chloride, concentrated sulfuric acid, hydrogen peroxide (30%), formic acid, boric acid, diethanolamine, diethylenetriamine, ethanolamine, N-(2-hydroxyethyl)ethylenediamine, tert-butyl chloride, and hexadecanol were all purchased from Sinopharm Chemical Reagent Co., Ltd. and were of analytical grade.

实施例1叔丁基化环氧腰果酚的制备Example 1 Preparation of tert-butylated epoxy cardanol

取100g腰果酚、8g甲酸、0.3g硫酸、200g双氧水,加入带有机械搅拌、回流冷凝器及温控的三口烧瓶中,开启搅拌、加热。维持反应温度为70℃,反应3小时。反应结束后降温,得到棕红色透明液体。将反应产物过滤后用5%KOH溶液进行碱洗,然后用蒸馏水水洗至中性,将有机相在100Pa、150℃条件下减压蒸馏1h,除去水分及没反应的原料,得到橙红色透明液体环氧化腰果酚。Take 100g of cardanol, 8g of formic acid, 0.3g of sulfuric acid, and 200g of hydrogen peroxide, add them to a three-necked flask with mechanical stirring, reflux condenser and temperature control, start stirring and heating. Maintain the reaction temperature at 70°C and react for 3 hours. After the reaction is completed, cool down to obtain a brown-red transparent liquid. Filter the reaction product and wash it with 5% KOH solution, then wash it with distilled water until neutral, and distill the organic phase under reduced pressure at 100Pa and 150°C for 1h to remove moisture and unreacted raw materials to obtain an orange-red transparent liquid epoxidized cardanol.

将35g环氧化腰果酚溶入100ml丙酮中,溶好后放入250ml三口反应烧瓶中,加入0.9g氯化锌催化剂,开启搅拌、加热。维持反应温度为60℃,将9.5g叔丁基氯缓慢滴加入反应烧瓶,滴加完毕后继续反应3小时。反应结束后降温,得到棕红色透明液体。将反应产物过滤后用5%KOH溶液进行碱洗,然后用蒸馏水水洗至中性,在1000Pa、120℃条件下减压蒸馏1h,除去溶剂、水分及没反应的原料,得到棕红色粘稠液体叔丁基化环氧腰果酚。Dissolve 35g of epoxidized cardanol in 100ml of acetone, put it into a 250ml three-necked reaction flask after dissolving, add 0.9g of zinc chloride catalyst, start stirring and heating. Maintain the reaction temperature at 60°C, slowly drop 9.5g of tert-butyl chloride into the reaction flask, and continue the reaction for 3 hours after the addition is complete. After the reaction is completed, cool down to obtain a brown-red transparent liquid. Filter the reaction product and wash it with 5% KOH solution, then wash it with distilled water until it is neutral, and distill it under reduced pressure at 1000Pa and 120°C for 1h to remove the solvent, moisture and unreacted raw materials to obtain a brown-red viscous liquid tert-butylated epoxidized cardanol.

上述反应的示例反应式如下式所示。An exemplary reaction formula of the above reaction is shown below.

Figure BDA0003299587390000111
Figure BDA0003299587390000111

实施例2Example 2

将22g实施例1制备的叔丁基化环氧腰果酚,5g N-(2-羟乙基)乙二胺及甲苯90g加入250mL三口烧瓶,在搅拌下加热,90℃反应3h。反应结束后,减压蒸馏1h,除去溶剂及没反应的原料,得到深棕红色粘稠液体叔丁基化氨基腰果酚,然后加入3g硼酸、10g N-(2-羟乙基)乙二胺以及90g环己烷加入反应容器中,搅拌、升温,脱去水分,在120℃反应3h,最后过滤、蒸除溶剂和未反应的N-(2-羟乙基)乙二胺,得到有机硼化合物W-01。22g of tert-butylated epoxy cardanol prepared in Example 1, 5g of N-(2-hydroxyethyl)ethylenediamine and 90g of toluene were added to a 250mL three-necked flask, heated under stirring, and reacted at 90°C for 3h. After the reaction was completed, the solvent and unreacted raw materials were removed by vacuum distillation for 1h to obtain dark brown viscous liquid tert-butylated amino cardanol, and then 3g of boric acid, 10g of N-(2-hydroxyethyl)ethylenediamine and 90g of cyclohexane were added to the reaction container, stirred, heated, dehydrated, reacted at 120°C for 3h, and finally filtered and evaporated to remove the solvent and unreacted N-(2-hydroxyethyl)ethylenediamine to obtain organic boron compound W-01.

反应的示例反应式如下式所示,其中的R为H。An example reaction formula of the reaction is shown below, where R is H.

Figure BDA0003299587390000121
Figure BDA0003299587390000121

将实施例2制备的产物进行红外光谱分析,分析结果见表1。The product prepared in Example 2 was subjected to infrared spectroscopy analysis. The analysis results are shown in Table 1.

表1产物红外分析结果Table 1 Infrared analysis results of products

Figure BDA0003299587390000122
Figure BDA0003299587390000122

表1中说明产物中存在C-OH伸缩振动峰、C-NH伸缩振动峰、苯环骨架伸缩振动峰、N-C伸缩振动峰、O-C伸缩振动峰以及B-O伸缩振动峰等特征峰,可以表明合成产物为目标化合物。Table 1 shows that the product has characteristic peaks such as C-OH stretching vibration peak, C-NH stretching vibration peak, benzene ring skeleton stretching vibration peak, N-C stretching vibration peak, O-C stretching vibration peak and B-O stretching vibration peak, which can indicate that the synthesized product is the target compound.

实施例3Example 3

将36g实施例1制备的叔丁基化环氧腰果酚,10g二乙醇胺及甲苯90g加入250mL三口烧瓶,在搅拌下加热,100℃反应4h。反应结束后,减压蒸馏1h,除去溶剂及没反应的原料,得到深棕红色粘稠液体叔丁基化氨基腰果酚,然后加入6g硼酸、20g二乙醇胺以及90g环己烷加入反应容器中,搅拌、升温,脱去水分,在150℃反应4h,最后过滤、蒸除溶剂和未反应的二乙醇胺,制备得到有机硼化合物W-02。36g of tert-butylated epoxy cardanol prepared in Example 1, 10g of diethanolamine and 90g of toluene were added to a 250mL three-necked flask, heated under stirring, and reacted at 100°C for 4h. After the reaction was completed, the solvent and unreacted raw materials were removed by vacuum distillation for 1h to obtain a dark brown viscous liquid tert-butylated amino cardanol, and then 6g of boric acid, 20g of diethanolamine and 90g of cyclohexane were added to the reaction vessel, stirred, heated, dehydrated, reacted at 150°C for 4h, and finally filtered and evaporated to remove the solvent and unreacted diethanolamine to prepare the organic boron compound W-02.

实施例4Example 4

将21.5g实施例1制备的叔丁基化环氧腰果酚,6g二乙烯三胺及甲苯90g加入250mL三口烧瓶,在搅拌下加热,95℃反应2h。反应结束后,减压蒸馏1h,除去溶剂及没反应的原料,得到深棕红色粘稠液体叔丁基化氨基腰果酚,然后加入6g硼酸、8g十六醇、10.5g二乙烯三胺以及90g环己烷加入反应容器中,搅拌、升温,脱去水分,在145℃反应5h,最后过滤、蒸除溶剂及未反应的二乙烯三胺,制备得到有机硼化合物W-03。21.5g of tert-butylated epoxy cardanol prepared in Example 1, 6g of diethylenetriamine and 90g of toluene were added to a 250mL three-necked flask, heated under stirring, and reacted at 95°C for 2h. After the reaction was completed, the solvent and unreacted raw materials were removed by vacuum distillation for 1h to obtain a dark brown viscous liquid tert-butylated amino cardanol, and then 6g of boric acid, 8g of hexadecanol, 10.5g of diethylenetriamine and 90g of cyclohexane were added to the reaction vessel, stirred, heated, dehydrated, reacted at 145°C for 5h, and finally filtered and evaporated to remove the solvent and unreacted diethylenetriamine to prepare the organic boron compound W-03.

对比例1Comparative Example 1

将36.3g十六醇、18.3g乙醇胺与6.2g硼酸以及90g甲苯溶剂加入反应容器中,搅拌、升温,在145℃反应6小时,最后过滤、蒸除溶剂及未反应的乙醇胺,得到对比有机硼化合物V-01。36.3 g of hexadecanol, 18.3 g of ethanolamine, 6.2 g of boric acid and 90 g of toluene solvent were added into a reaction container, stirred, heated, and reacted at 145° C. for 6 hours. Finally, the solvent and unreacted ethanolamine were filtered and evaporated to obtain comparative organic boron compound V-01.

空气压缩机润滑油组合物的实施例5-7与对比例2-3Examples 5-7 and Comparative Examples 2-3 of Air Compressor Lubricant Compositions

按照表2的配方组成调制得到空气压缩机润滑油组合物的实施例5-7与对比例2-3,其中所使用的主要添加剂和润滑基础油来源如下:According to the formula composition in Table 2, Examples 5-7 and Comparative Examples 2-3 of the air compressor lubricant oil compositions were prepared, wherein the main additives and lubricant base oils used were from the following sources:

抗氧剂T501,石油化工科院研究院兴普公司,工业品Antioxidant T501, Petrochemical Research Institute Xingpu Company, Industrial Products

硫磷酸含氮衍生物T305,沈阳华仑润滑油添加剂有限公司,工业品Sulfur phosphoric acid nitrogen derivative T305, Shenyang Hualun Lubricant Additives Co., Ltd., industrial products

丙烯酸与醚的共聚物T911,沈阳聚鑫天成化工有限公司,工业品Copolymer of acrylic acid and ether T911, Shenyang Juxin Tiancheng Chemical Co., Ltd., Industrial products

癸二酸二异辛酯,北京化工三厂,工业品Diisooctyl sebacate, Beijing Chemical Plant No. 3, industrial products

表2空气压缩机润滑油组合物的实施例及比较例Table 2 Examples and Comparative Examples of Air Compressor Lubricant Compositions

Figure BDA0003299587390000141
Figure BDA0003299587390000141

分别对上述实施例、对比例的空气压缩机润滑油组合物进行了高温抗氧化性能润滑油氧化诱导期评定,测定方法为SH/T 0719,测试仪器为美国TA公司TA5000型号DSC仪,测试条件为:190℃,氧压0.5MPa,升温速度10℃/min。The high temperature oxidation resistance and oxidation induction period of the air compressor lubricating oil compositions of the above-mentioned embodiments and comparative examples were evaluated respectively. The determination method was SH/T 0719, the testing instrument was a TA5000 DSC instrument of TA Company of the United States, and the testing conditions were: 190°C, oxygen pressure 0.5MPa, and heating rate 10°C/min.

分别对上述实施例、对比例的空气压缩机润滑油组合物进行了润滑油抗磨损性能的测定,测定方法为四球法SH/T 0189,测试仪器为美国Koehler公司生产的K93190型四球试验机,测试条件为1200rpm,75℃,392N,60min。The anti-wear performance of the air compressor lubricating oil compositions of the above-mentioned embodiments and comparative examples was measured respectively, the measuring method was the four-ball method SH/T 0189, the testing instrument was the K93190 four-ball testing machine produced by Koehler Company of the United States, and the testing conditions were 1200rpm, 75℃, 392N, 60min.

高温抗氧化性能、抗磨损性能的评定结果如表3所示。The evaluation results of high temperature oxidation resistance and wear resistance are shown in Table 3.

表3Table 3

样品sample 氧化诱导期/minOxidation induction period/min 磨斑直径/mmWear spot diameter/mm 实施例5Example 5 19.819.8 0.520.52 实施例6Example 6 18.518.5 0.580.58 实施例7Example 7 17.617.6 0.630.63 对比例2Comparative Example 2 10.210.2 0.770.77 对比例3Comparative Example 3 14.714.7 0.700.70

Claims (10)

1.空气压缩机润滑油组合物,以质量百分比计,包括0.1%~10%的有机硼化合物、0.01%~5%的抗氧剂、0.01%~5%的极压抗磨剂、0.001%~1%的消泡剂和主要量的酯类润滑基础油,其中有机硼化合物的结构如式(I)所示:1. An air compressor lubricant composition, comprising, by mass percentage, 0.1% to 10% of an organic boron compound, 0.01% to 5% of an antioxidant, 0.01% to 5% of an extreme pressure anti-wear agent, 0.001% to 1% of a defoaming agent, and a major amount of an ester lubricating base oil, wherein the structure of the organic boron compound is as shown in formula (I):
Figure FDA0003299587380000011
Figure FDA0003299587380000011
在式(I)中,存在a个重复单元L和b个含硼基团,a为1~10之间的整数(优选1~5之间的整数),b为1~5之间的整数(优选1~3之间的整数),a个L基团彼此相同或不同,各自独立地选自式(II)所示的基团;In formula (I), there are a repeating unit L and b boron-containing groups, a is an integer between 1 and 10 (preferably an integer between 1 and 5), b is an integer between 1 and 5 (preferably an integer between 1 and 3), and a L groups are the same or different and are independently selected from the group represented by formula (II);
Figure FDA0003299587380000012
Figure FDA0003299587380000012
在式(II)中,HO与苯环键合(HO优选位于苯环上R1所在链的间位);y个R基团与苯环键合;y选自0~4之间的整数(优选1~3之间的整数);R基团各自独立地选自H和C1-20直链或支链烷基(优选各自独立地选自H和C1-4直链或支链烷基,更优选叔丁基);n为1~10之间的整数(优选1~3之间的整数);R1各自独立地选自单键和C1-20直链或支链的亚烷基(优选选自单键和C1-4直链或支链的亚烷基);n个重复单元中的R2彼此相同或不同,各自独立地选自单键和C1-20直链或支链的亚烷基(优选各自独立地选自单键和C1-4直链或支链的亚烷基);R3选自H和C1-20直链或支链烷基(优选选自H和C1-4直链或支链烷基);n个重复单元中的A基团彼此相同或不同,各自独立地选自单键、
Figure FDA0003299587380000013
式(III)所示的基团和式(IV)所示的基团,
In formula (II), HO is bonded to the benzene ring (HO is preferably located at the meta position of the chain where R 1 is located on the benzene ring); y R groups are bonded to the benzene ring; y is selected from an integer between 0 and 4 (preferably an integer between 1 and 3); the R groups are each independently selected from H and C 1-20 straight or branched alkyl (preferably each independently selected from H and C 1-4 straight or branched alkyl, more preferably tert-butyl); n is an integer between 1 and 10 (preferably an integer between 1 and 3); R 1 is each independently selected from a single bond and a C 1-20 straight or branched alkylene (preferably selected from a single bond and a C 1-4 straight or branched alkylene); R 2 in the n repeating units are the same or different from each other and are each independently selected from a single bond and a C 1-20 straight or branched alkylene (preferably each independently selected from a single bond and a C 1-4 straight or branched alkylene); R 3 is selected from H and a C 1-20 straight or branched alkyl (preferably selected from H and C 1-4 straight or branched alkyl groups); the A groups in the n repeating units are the same or different from each other and are independently selected from a single bond,
Figure FDA0003299587380000013
The group represented by formula (III) and the group represented by formula (IV),
Figure FDA0003299587380000021
Figure FDA0003299587380000021
所述R4基团各自独立地选自H和C1-20直链或支链烷基(优选选自H和C1-4直链或支链烷基);The R4 groups are each independently selected from H and C1-20 straight or branched alkyl (preferably selected from H and C1-4 straight or branched alkyl); m为0~10之间的整数(优选1~5之间的整数);m is an integer between 0 and 10 (preferably an integer between 1 and 5); 所述的R5基团各自独立地选自3价的C1-20直链或支链烷基(优选各自独立地选自3价的C1-4直链或支链烷基);The R 5 groups are each independently selected from a trivalent C 1-20 straight chain or branched chain alkyl group (preferably each independently selected from a trivalent C 1-4 straight chain or branched chain alkyl group); 各个G2基团各自独立地选自与其所在L基团之外的其它L基团中存在的G4基团键合的结合端、C1-10直链或支链的烷基、-R6G3、H;各个G3基团各自独立地选自-OG1、C1-10直链或支链的烷基、H(优选各自独立地选自-OG1、C1-4直链或支链的烷基、OH、H);Each G2 group is independently selected from the group bonded to the G4 group present in the other L group other than the L group in which it is located, a C1-10 straight or branched alkyl group, -R6G3 , and H; each G3 group is independently selected from -OG1 , a C1-10 straight or branched alkyl group, and H (preferably, independently selected from -OG1 , a C1-4 straight or branched alkyl group, OH, and H); 所述的R6基团选自C1-20直链或支链的亚烷基(优选各自独立地选自C1-4直链或支链的亚烷基);The R 6 groups are selected from C 1-20 straight or branched alkylene groups (preferably each independently selected from C 1-4 straight or branched alkylene groups); G1基团选自与所述含硼基团键合的结合端、H;The G1 group is selected from the binding end bonded to the boron-containing group, H; G4基团选自与其所在L基团之外的其它L基团中存在的G2基团键合的结合端、H;The G4 group is selected from the binding end bonded to the G2 group present in other L groups other than the L group in which it is located, H; 在a个L基团中,至少存在一个A基团选自式(III)所示的基团,至少存在一个G1基团选自与含硼基团中的硼元素键合的结合端;Among a L groups, at least one A group is selected from the group represented by formula (III), and at least one G1 group is selected from the binding end bonded to the boron element in the boron-containing group; b个所述含硼基团中的各个A’基团各自独立地选自与L基团中存在的G1基团键合的结合端、式(V)所示的基团、-OR’,所述的R’基团为H或C1-20直链或支链的烷基(优选为H或C1-4直链或支链的烷基);Each A' group in the b boron-containing groups is independently selected from the binding end bonded to the G1 group present in the L group, the group represented by formula (V), -OR', and the R' group is H or a C 1-20 straight or branched alkyl group (preferably H or a C 1-4 straight or branched alkyl group);
Figure FDA0003299587380000031
Figure FDA0003299587380000031
在式(V)中,m为0~10之间的整数(优选1~5之间的整数);In formula (V), m is an integer between 0 and 10 (preferably an integer between 1 and 5); 所述的R0基团各自独立地选自C1-10直链或支链烷基、-R6G5、H(优选各自独立地选自C1-4直链或支链烷基、-R6G5、H);The R 0 groups are each independently selected from C 1-10 straight or branched alkyl, -R 6 G 5 , H (preferably each independently selected from C 1-4 straight or branched alkyl, -R 6 G 5 , H); 所述的R5基团各自独立地选自3价的C1-20直链或支链烷基(优选各自独立地选自3价的C1-4直链或支链烷基);The R 5 groups are each independently selected from a trivalent C 1-20 straight chain or branched chain alkyl group (preferably each independently selected from a trivalent C 1-4 straight chain or branched chain alkyl group); G6基团选自-R6G5、C1-4直链或支链的烷基、H;The G6 group is selected from -R6G5 , C1-4 straight or branched alkyl, H; 所述的R6基团选自C1-20直链或支链的亚烷基(优选各自独立地选自C1-4直链或支链的亚烷基);The R 6 groups are selected from C 1-20 straight or branched alkylene groups (preferably each independently selected from C 1-4 straight or branched alkylene groups); 各个G5基团各自独立地选自-OG1、C1-4直链或支链的烷基、OH、H,其中的G1基团选自与所述含硼基团中的硼元素键合的结合端、C1-4直链或支链的烷基、H;Each G 5 group is independently selected from -OG 1 , C 1-4 straight or branched alkyl, OH, H, wherein the G 1 group is selected from the binding end bonded to the boron element in the boron-containing group, C 1-4 straight or branched alkyl, H; 在式(V)所示的基团中,至少存在一个G1基团选自与含硼基团中的硼元素键合的结合端;In the group represented by formula (V), there is at least one G1 group selected from the binding end bonded to the boron element in the boron-containing group; 在b个所述含硼基团中,至少存在一个A’基团选自与L基团中存在的G1基团键合的结合端;Among the b said boron-containing groups, at least one A' group is selected from the binding end bonded to the G1 group present in the L group; 所述有机硼化合物中的各个基团符合成键规则。Each group in the organic boron compound complies with the bonding rules.
2.按照权利要求1所述的润滑油组合物,其特征在于,所述有机硼化合物包括以下结构化合物中的一种或多种:2. The lubricating oil composition according to claim 1, characterized in that the organic boron compound comprises one or more of the following structural compounds:
Figure FDA0003299587380000041
Figure FDA0003299587380000041
Figure FDA0003299587380000051
Figure FDA0003299587380000051
其中的R基团为H或C1-C20的直链或支链烷基。The R group is H or a C 1 -C 20 straight or branched chain alkyl group.
3.按照权利要求1所述的润滑油组合物,其特征在于,所述有机硼化合物的制备方法包括以下步骤:3. The lubricating oil composition according to claim 1, characterized in that the preparation method of the organic boron compound comprises the following steps: (1)使式(X)所示的化合物与过氧化物反应;(1) reacting a compound represented by formula (X) with a peroxide;
Figure FDA0003299587380000052
Figure FDA0003299587380000052
在式(X)中,HO与苯环键合(HO优选位于苯环上R1所在链的间位);y个R基团与苯环键合;y选自0~4之间的整数(优选1~3之间的整数);R基团各自独立地选自H和C1-20直链或支链烷基(优选各自独立地选自H和C1-4直链或支链烷基,更优选选自叔丁基);n为1~10之间的整数(优选1~3之间的整数);R1各自独立地选自单键和C1-20直链或支链的亚烷基(优选选自单键和C1-4直链或支链的亚烷基);n个重复单元中的R2彼此相同或不同,各自独立地选自单键和C1-20直链或支链的亚烷基(优选各自独立地选自单键和C1-4直链或支链的亚烷基);R3选自H和C1-20直链或支链烷基(优选选自H和C1-4直链或支链烷基);n个重复单元中的A”彼此相同或不同,各自独立地选自单键、
Figure FDA0003299587380000061
其中所述的R4基团各自独立地选自H和C1-20直链或支链烷基(优选选自H和C1-4直链或支链烷基);在式(X)中至少存在一个A”为
Figure FDA0003299587380000062
In formula (X), HO is bonded to the benzene ring (HO is preferably located at the meta position of the chain where R 1 is located on the benzene ring); y R groups are bonded to the benzene ring; y is selected from an integer between 0 and 4 (preferably an integer between 1 and 3); the R groups are each independently selected from H and C 1-20 straight or branched alkyl (preferably each independently selected from H and C 1-4 straight or branched alkyl, more preferably selected from tert-butyl); n is an integer between 1 and 10 (preferably an integer between 1 and 3); R 1 is each independently selected from a single bond and a C 1-20 straight or branched alkylene (preferably selected from a single bond and a C 1-4 straight or branched alkylene); R 2 in the n repeating units are the same or different from each other and are each independently selected from a single bond and a C 1-20 straight or branched alkylene (preferably each independently selected from a single bond and a C 1-4 straight or branched alkylene); R 3 is selected from H and C 1-20 straight or branched chain alkyl groups (preferably selected from H and C 1-4 straight or branched chain alkyl groups); A" in the n repeating units are the same or different from each other and are independently selected from single bonds,
Figure FDA0003299587380000061
wherein the R4 groups are independently selected from H and C1-20 straight chain or branched alkyl (preferably selected from H and C1-4 straight chain or branched alkyl); in formula (X), at least one A" is
Figure FDA0003299587380000062
(2)使步骤(1)的反应产物与式(Y)所示的化合物反应;(2) reacting the reaction product of step (1) with a compound represented by formula (Y);
Figure FDA0003299587380000063
Figure FDA0003299587380000063
在式(Y)中,m为0~10之间的整数(优选1~5之间的整数);In formula (Y), m is an integer between 0 and 10 (preferably an integer between 1 and 5); 所述的R0’基团各自独立地选自C1-10直链或支链烷基、-R6OH、H(优选各自独立地选自C1-4直链或支链烷基、-R6OH、H);所述的R5基团各自独立地选自3价的C1-20直链或支链烷基(优选各自独立地选自3价的C1-4直链或支链烷基);各个G5’基团各自独立地选自C1-4直链或支链的烷基、OH、H;所述的G6’基团选自C1-10直链或支链的烷基、-R6OH、H;所述的R6基团各自独立地选自C1-20直链或支链的亚烷基(优选各自独立地选自C1-4直链或支链的亚烷基);The R 0 'groups are each independently selected from C 1-10 straight or branched alkyl, -R 6 OH, H (preferably each independently selected from C 1-4 straight or branched alkyl, -R 6 OH, H); the R 5 groups are each independently selected from trivalent C 1-20 straight or branched alkyl (preferably each independently selected from trivalent C 1-4 straight or branched alkyl); each G 5 'group is each independently selected from C 1-4 straight or branched alkyl, OH, H; the G 6 'group is selected from C 1-10 straight or branched alkyl, -R 6 OH, H; the R 6 groups are each independently selected from C 1-20 straight or branched alkylene (preferably each independently selected from C 1-4 straight or branched alkylene); 在式(Y)中,至少存在一个G5’基团选自OH或者至少一个G6’基团或R0’基团选自-R6OH,并且至少存在一个R0’基团或G6’基团为H;In formula (Y), there is at least one G 5 'group selected from OH or at least one G 6 'group or R 0 'group selected from -R 6 OH, and at least one R 0 'group or G 6 'group is H; (3)使步骤(2)的反应产物与无机硼化合物反应,收集产物。(3) reacting the reaction product of step (2) with an inorganic boron compound and collecting the product.
4.按照权利要求3所述的润滑油组合物,其特征在于,4. The lubricating oil composition according to claim 3, characterized in that 在步骤(1)中,式(X)所示的化合物选自腰果酚、烷基化腰果酚;和/或,所述过氧化物选自双氧水、过氧甲酸、过氧乙酸、过氧磺酸、间氯过氧苯甲酸、叔丁基过氧化氢、过氧乙酸叔丁酯、过氧化甲基乙基酮、过氧化二苯甲酰和过氧化环己酮中的一种或多种;In step (1), the compound represented by formula (X) is selected from cardanol and alkylated cardanol; and/or the peroxide is selected from one or more of hydrogen peroxide, performic acid, peracetic acid, persulfonic acid, m-chloroperbenzoic acid, tert-butyl hydroperoxide, tert-butyl peracetate, methyl ethyl ketone peroxide, dibenzoyl peroxide and cyclohexanone peroxide; 和/或,在步骤(2)中,式(Y)所示的化合物选自脂肪胺、多烯多胺、一个或多个羟基取代的脂肪胺、一个或多个羟基取代的多烯多胺中的一种或多种;And/or, in step (2), the compound represented by formula (Y) is selected from one or more of aliphatic amines, polyene polyamines, aliphatic amines substituted with one or more hydroxy groups, and polyene polyamines substituted with one or more hydroxy groups; 和/或,在步骤(3)中,所述无机硼化合物选自硼酸、氧化硼和硼酸半酯中的一种或多种。And/or, in step (3), the inorganic boron compound is selected from one or more of boric acid, boric oxide and boric acid half ester. 5.按照权利要求3所述的润滑油组合物,其特征在于,式(X)所示的化合物与过氧化物、式(Y)所示的化合物、无机硼化合物之间的当量比为1:0.5~10:0.5~10:0.5~5(优选为1:2~3:2~3:1~2)。5. The lubricating oil composition according to claim 3, characterized in that the equivalent ratio between the compound represented by formula (X), the peroxide, the compound represented by formula (Y), and the inorganic boron compound is 1:0.5-10:0.5-10:0.5-5 (preferably 1:2-3:2-3:1-2). 6.按照权利要求3所述的润滑油组合物,其特征在于,步骤(1)的反应温度为0~100℃,(优选为20~80℃);步骤(2)的反应温度为50~150℃(优选为60~100℃);步骤(3)的反应温度为80~200℃(优选为110~150℃)。6. The lubricating oil composition according to claim 3, characterized in that the reaction temperature of step (1) is 0-100°C (preferably 20-80°C); the reaction temperature of step (2) is 50-150°C (preferably 60-100°C); and the reaction temperature of step (3) is 80-200°C (preferably 110-150°C). 7.按照权利要求3所述的润滑油组合物,其特征在于,步骤(1)的反应时间为1~10h(优选为3~5h);步骤(2)的反应时间为1~10h(优选为2~4h);步骤(3)的反应时间为1~10h(优选为3~5h)。7. The lubricating oil composition according to claim 3, characterized in that the reaction time of step (1) is 1 to 10 hours (preferably 3 to 5 hours); the reaction time of step (2) is 1 to 10 hours (preferably 2 to 4 hours); and the reaction time of step (3) is 1 to 10 hours (preferably 3 to 5 hours). 8.按照权利要求1~7之一所述的润滑油组合物,其特征在于,所述抗氧剂选自酚型抗氧剂;所述极压抗磨剂选自硫磷酸含氮衍生物、磷酸酯、亚磷酸酯、硫代磷酸胺盐、硫化烯烃和二烷基二硫代氨基甲酸盐中的一种或多种;所述消泡剂选自丙烯酸与醚的共聚物、甲基硅油和乙基硅油中的一种或多种;所述酯类润滑基础油为双酯类润滑基础油。8. The lubricating oil composition according to any one of claims 1 to 7, characterized in that the antioxidant is selected from phenolic antioxidants; the extreme pressure anti-wear agent is selected from one or more of sulfuric acid nitrogen derivatives, phosphates, phosphites, thiophosphate amine salts, sulfided olefins and dialkyl dithiocarbamates; the defoaming agent is selected from one or more of copolymers of acrylic acid and ether, methyl silicone oil and ethyl silicone oil; the ester lubricating base oil is a diester lubricating base oil. 9.按照权利要求1~7之一所述的润滑油组合物,其特征在于,所述空气压缩机润滑油组合物,以质量百分比计,以质量百分比计,包括0.2%~5%的有机硼化合物、0.01%~3%的抗氧剂、0.01%~3%的极压抗磨剂、0.001%~0.5%的消泡剂和主要量的酯类润滑基础油。9. The lubricating oil composition according to any one of claims 1 to 7, characterized in that the air compressor lubricating oil composition comprises, by mass percentage, 0.2% to 5% of an organic boron compound, 0.01% to 3% of an antioxidant, 0.01% to 3% of an extreme pressure anti-wear agent, 0.001% to 0.5% of a defoaming agent and a major amount of an ester lubricating base oil. 10.权利要求1~9之一所述的空气压缩机润滑油组合物的制备方法,包括将所述的空气压缩机润滑油组合物中的添加剂和润滑基础油混合的步骤。10. The method for preparing the air compressor lubricant oil composition according to any one of claims 1 to 9, comprising the step of mixing the additive in the air compressor lubricant oil composition with a lubricating base oil.
CN202111186803.7A 2021-10-12 2021-10-12 Air compressor lubricating oil composition and preparation method thereof Active CN115960650B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202111186803.7A CN115960650B (en) 2021-10-12 2021-10-12 Air compressor lubricating oil composition and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202111186803.7A CN115960650B (en) 2021-10-12 2021-10-12 Air compressor lubricating oil composition and preparation method thereof

Publications (2)

Publication Number Publication Date
CN115960650A true CN115960650A (en) 2023-04-14
CN115960650B CN115960650B (en) 2024-08-09

Family

ID=87357428

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202111186803.7A Active CN115960650B (en) 2021-10-12 2021-10-12 Air compressor lubricating oil composition and preparation method thereof

Country Status (1)

Country Link
CN (1) CN115960650B (en)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4507216A (en) * 1983-03-14 1985-03-26 Mobil Oil Corporation Hindered phenyl esters of cyclic borates and lubricants containing same
CN101597535A (en) * 2009-06-30 2009-12-09 王严绪 A kind of novel organic nitrogen-containing borate ester lubricating oil additive
CN105586135A (en) * 2014-10-23 2016-05-18 中国石油化工股份有限公司 Urea-based lubricating grease composition with excellent antifriction property and preparation method therefor
CN107690471A (en) * 2015-06-04 2018-02-13 雪佛龙奥伦耐有限责任公司 Boronation polyol ester antioxidant/friction improver of hindered phenol with enhancing performance
CN110691838A (en) * 2017-05-31 2020-01-14 道达尔销售服务公司 Compounds comprising polyamine, acid and boron functional groups and their use as lubricant additives
CN111057108A (en) * 2018-10-16 2020-04-24 中国石油化工股份有限公司 Phosphoramidate compound and preparation method and application thereof
US20200361964A1 (en) * 2019-05-17 2020-11-19 Vanderbilt Chemicals, Llc Less corrosive organoboron compounds as lubricant additives

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4507216A (en) * 1983-03-14 1985-03-26 Mobil Oil Corporation Hindered phenyl esters of cyclic borates and lubricants containing same
CN101597535A (en) * 2009-06-30 2009-12-09 王严绪 A kind of novel organic nitrogen-containing borate ester lubricating oil additive
CN105586135A (en) * 2014-10-23 2016-05-18 中国石油化工股份有限公司 Urea-based lubricating grease composition with excellent antifriction property and preparation method therefor
CN107690471A (en) * 2015-06-04 2018-02-13 雪佛龙奥伦耐有限责任公司 Boronation polyol ester antioxidant/friction improver of hindered phenol with enhancing performance
CN110691838A (en) * 2017-05-31 2020-01-14 道达尔销售服务公司 Compounds comprising polyamine, acid and boron functional groups and their use as lubricant additives
CN111057108A (en) * 2018-10-16 2020-04-24 中国石油化工股份有限公司 Phosphoramidate compound and preparation method and application thereof
US20200361964A1 (en) * 2019-05-17 2020-11-19 Vanderbilt Chemicals, Llc Less corrosive organoboron compounds as lubricant additives

Also Published As

Publication number Publication date
CN115960650B (en) 2024-08-09

Similar Documents

Publication Publication Date Title
CN115960650B (en) Air compressor lubricating oil composition and preparation method thereof
CN114478200B (en) A phenol derivative and its preparation method and use
CN115960666B (en) Air compressor lubricating oil composition and preparation method thereof
EP4406959A1 (en) Organoboron compound, preparation method therefor and use thereof
CN115960648B (en) Gasoline engine oil composition and preparation method thereof
CN115960661B (en) Diesel engine oil composition and preparation method thereof
CN114426464B (en) A phenol derivative and its preparation method and use
CN111088098A (en) High-temperature chain oil composition and preparation method thereof
CN115960660B (en) Lubricating oil composition for gasoline engine and preparation method thereof
CN115975701B (en) Marine medium-speed trunk piston engine lubricating oil composition and preparation method thereof
CN115975704B (en) Lubricating oil composition for medium-high speed diesel engine of railway and preparation method thereof
CN115960662B (en) Lubricating oil composition for gas engine and preparation method thereof
CN115960663B (en) Methanol fuel engine lubricating oil composition and preparation method thereof
CN109679721B (en) Industrial lubricating oil composition and preparation method thereof
CN117247410A (en) Organophosphorus compounds and preparation methods and uses thereof
CN115992023B (en) Lubricating grease and preparation method thereof
CN117264685A (en) Diesel engine oil composition
CN115960649B (en) Grease and preparation method thereof
CN115975696A (en) Diesel engine lubricating oil composition and preparation method thereof
CN117384696A (en) Methanol fuel engine lubricating oil composition
CN117384695A (en) Gasoline engine lubricating oil composition
CN115975702B (en) Gasoline engine oil composition and preparation method thereof
CN115960664B (en) Worm gear oil composition and preparation method thereof
CN115960656B (en) Composite lithium-based lubricating grease and preparation method thereof
CN113388438B (en) Worm gear oil composition, preparation method and use thereof

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant