Benzotriazole derivative, preparation process and the use thereof

Patent metadata

Field	Value
Publication number	US-10822359-B2
Application number	US-201716097092-A
Country	US
Kind code	B2
Filing date	Apr 25, 2017
Priority date	Apr 27, 2016
Publication date	Nov 3, 2020
Grant date	Nov 3, 2020

Abstract

The present invention relates to a benzotriazole derivative, a preparation process thereof and the use thereof in preparation of the lubricating oil composition. The structure of the benzotriazole derivative of the present invention is shown by general formula (I). The benzotriazole derivative of the present invention, as the anti-wear additive for lubricating oil, not only has an excellent extreme pressure anti-wear property, but also has one or more excellent properties of thermal oxidation stability, corrosion resistance, rust resistance and anti-friction performance.

In the general formula (I), each of the group(s) and the number(s) are defined as in the description.

First claim

The invention claimed is:

1. A benzotriazole derivative of formula (I):

wherein, in formula (I), R′ is chosen from a C 1-25 hydrocarbyl, a C 3-25 inear or branched heteroalkyl, a hydrocarbyl having a number-average molecular weight Mn of 300-3000, or a polyisobutenyl having a number-average molecular weight Mn of 300-3000; n is an integer of 0-10;
the n R 0 groups in formula (I) are identical to or different from each other and each independently is a C 1-10 linear or branched alkylene; the n+2 A groups in formula (I) are identical to or different from each other and each independently is hydrogen, a group represented by formula (I-1), a group represented by formula (I-2), a C 1-25 hydrocarbyl, or a hydrocarbyl having a number-average molecular weight Mn of 300-3000, pq, 59 provided that at least one of said n+2 A groups in formula (I) is a group represented by formula (I-1), and at least one of said n+2 A groups in formula (I) is a group represented by formula (I-2);
wherein, when said at least one of said n+2 A groups in formula (I) is a C 10-25 linear or branched alkyl, a C 10-25 linear or branched alkenyl, or a hydrocarbyl having a number-average molecular weight Mn of 300-3000, is optionally hydrogen,

wherein, in formula (I-1) and formula (I-2), R 5 and R 6 are identical to or different from each other and each independently is a C 1-20 hydrocarbyl the two Y groups in formula (I-2) are identical to or different from each other and each independently is an oxygen atom or a sulfur atom, the two X groups in formula (I-2) are both sulfur atoms; the two R″ groups in formula (I-1) and formula (I-2) are identical to or different from each other and each independently is hydrogen or a C 1-20 hydrocarbyl; R 1 , R 2 , R 3 , and R 4 are identical to or different from each other and each independently is hydrogen or a C 1-20 hydrocarbyl, and
wherein one of R 2 and R 3 is a C 1-10 linear or branched alkyl and the other is hydrogen,
wherein said linear or branched heteroalkyl refers to a group obtained by inserting one or more hetero groups chosen from —O—, —S—, or —NR— (wherein the group R is H or a C 1-4 linear or branched alkyl) into the carbon chain of a linear or branched alkyl.

2. The benzotriazole derivative according to claim 1 , which is

3. A process for preparing a benzotriazole derivative, comprising the step of reacting a phosphorus compound represented by formula (I-A), an amine compound represented by formula (I-B), and a benzotriazole compound represented by formula (I-C) in presence of an aldehyde represented by formula (I-D),

wherein R′ is chosen from a C 1-25 hydrocarbyl, a C 3-25 linear or branched heteroalkyl, a hydrocarbyl having a number-average molecular weight Mn of 300-3000; n is an integer of 0-10; the n R 0 groups in formula (I-B) are identical to or different from each other and each independently is a C 1-10 linear or branched alkylene; the n+2 A′ groups in formula (I-B) are identical to or different from each other and each independently is hydrogen, a C 1-25 hydrocarbyl, or a hydrocarbyl having a number-average molecular weight Mn of 300-3000, provided that at least two of said n+2 A′ groups in formula (I-B) represent hydrogen; when at least one of said n+2 A′ groups in formula (I-B) is a C 10-25 linear or branched alkyl, a C 10-25 linear or branched alkenyl, or a hydrocarbyl having a number-average molecular weight Mn of 300-3000, said group R′ is optionally hydrogen; R 5 and R 6 are identical to or different from each other and each independently is a C 1-20 hydrocarbyl; the two Y groups in formula (I-A) are identical to or different from each other and each independently is an oxygen atom or a sulfur atom, the two X groups in formula (I-A) are both sulfur atoms; R″ is hydrogen and a C 1-20 hydrocarbyl; R 1 , R 2 , R 3 , and R 4 are identical to or different from each other and each independently is hydrogen or a C 1-20 hydrocarbyl, and one of R 2 and R 3 is a C 1-10 linear or branched alkyl, the other is hydrogen,
said linear or branched heteroalkyl refers to a group obtained by inserting one or more hetero groups chosen from —O—, —S— or —NR— (wherein the group R is H or a C 1-4 linear or branched alkyl) into the carbon chain of a linear or branched alkyl.

4. The preparation process according to claim 3 , wherein the reaction time of said reaction is 0.1-24 h, and the reaction temperature of said reaction is 0-250° C.

5. The preparation process according to claim 3 , wherein a molar ratio of said phosphorus compound represented by formula (I-A) to said amine compound represented by formula (I-B) is 1:0.1-10; a molar ratio of said phosphorus compound represented by formula (I-A) to said benzotriazole compound represented by formula (I-C) is 1:0.1-10; and a molar ratio of said phosphorus compound represented by formula (I-A) to said aldehyde represented by formula (I-D) is 1:1-10.

6. A method for preparing a lubricating oil, comprising adding the benzotriazole derivative according to claim 1 into a base oil.

7. A lubricating oil composition, containing a base oil for lubricating oil, and the benzotriazole derivative according to claim 1 .

8. The lubricating oil composition according to claim 7 , wherein on the weight basis, said benzotriazole derivative is 0.001-30% by the total weight of said lubricating oil composition.

9. A method for preparing a lubricating oil, comprising adding the benzotriazole derivative obtained by the preparation process according to claim 3 into a base oil.

10. A lubricating oil composition, containing a base oil for lubricating oil, and the benzotriazole derivative obtained by the preparation process according to claim 3 .

Assignees

• China Petroleum & Chem Corp
• Sinopec Res Inst Petroleum

Inventors

• Su Shuo
• Long Jun
• Duan Qinghua
• Zhang Hui

Classifications

• C10M137/105 Primary

  not containing metal · CPC title

• C10M169/04

  Mixtures of base-materials and additives · CPC title

• C10M137/10

  Thio derivatives · CPC title

• C07F9/65188 Primary

  condensed with carbocyclic rings or carbocyclic ring systems · CPC title

• C10N2030/06

  Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure · CPC title