Multifunctional branched polymers with improved low-temperature performance

Patent metadata

Field	Value
Publication number	US-11760953-B2
Application number	US-202117376604-A
Country	US
Kind code	B2
Filing date	Jul 15, 2021
Priority date	Apr 25, 2018
Publication date	Sep 19, 2023
Grant date	Sep 19, 2023

Abstract

A viscosity index improver comprising a reaction product of (i) an acylated copolymer obtainable by acylating a copolymer of ethylene and one or more C3-C10 alpha-olefins having an Mn of 3,000 to 250,000 g/mol; and (ii) a compound of the formulae (III)-(V):wherein R6, R8, R9, R10, R12 and R15 are independently selected from a hydrogen and an optionally substituted linear or branched alkyl or alkenyl group, and R7, R11, R13, R14, R16, and R17 are independent selected from an optionally substituted linear or branched alkyl or alkenyl group, and a sum of the number of carbon atoms in each compound of the formulae (III)-(V) is from 6 to 31.

First claim

What is claimed is:

1. A viscosity index improver comprising a reaction product of
(i) an acylated copolymer obtainable by acylating, with an acylating agent, a copolymer of ethylene and one or more C 3 -C 10 alpha-olefins having a number average molecular weight of 3,000 g/mol to 250,000 g/mol as measured by GPC,
wherein an ethylene content of the copolymer of ethylene and one or more C 3 -C 10 alpha-olefins is 10 mol % to 70 mol % and the C 3 -C 10 alpha-olefin content of the copolymer of ethylene and one or more C 3 -C 10 alpha-olefins includes at least 40 mol % of propylene when the one or more C 3 -C 10 alpha-olefins comprises propylene; and
(ii) a compound selected from one or more compounds of the formulae (III)-(V):

wherein R 6 is selected from a hydrogen and a linear or branched alkyl or alkenyl group, and R 7 is a linear or branched alkyl or alkenyl group, and a sum of a number of carbon atoms of R 6 and R 7 is from 7 to 31;

wherein R 8 , R 9 and R 10 are independently selected from a hydrogen and a linear or branched alkyl or alkenyl group; and R 11 is selected from a linear or branched alkyl or alkenyl group, and a sum of a number of carbon atoms of R 8 , R 9 , R 10 and R 11 is from 6 to 30; and

wherein R 13 , R 14 , R 16 , and R 17 are independently selected from a linear or branched alkyl or alkenyl group; R 12 and R 15 are independently selected from hydrogen and a linear or branched alkyl or alkenyl group, a sum of a number of carbon atoms of R 12 , R 13 , R 14 , R 15 , R 16 and R 17 is from 6 to 30, and only one of R 12 and R 15 can be hydrogen; and
the alkyl or alkenyl groups of the compounds of the formulae (III)-(V) are optionally substituted with one or more of halo groups, alkoxy groups, mercapto groups, nitro groups, nitroso groups, sulfoxy groups, pyridyl groups, furyl groups, thienyl groups, imidazolyl groups, and sulfur, and no more than two non-hydrocarbon substituents are present for every ten carbon atoms in the alkyl or alkenyl group, and
the ratio of moles of amine per mole of carboxyl groups of the acylated polymer, is from 0.25:1 to 4:1.

2. The viscosity index improver of claim 1 , wherein one or more of R 7 , R 11 , and R 13 is an alkyl group or an alkenyl group that provides branching at one or more of an alpha and a beta carbon atom of the compound (ii).

3. The viscosity index improver of claim 1 , wherein one or more of R 7 , R 11 , and R 13 is an alkyl group or an alkenyl group that provides branching at at least an alpha carbon atom of the compound (ii).

4. The viscosity index improver of claim 1 , wherein one or more of R 7 , R 11 , and R 13 is an alkyl group or an alkenyl group that provides branching at at least a beta carbon atom of the compound (ii).

5. The viscosity index improver of claim 1 , wherein the compound (ii) is a compound of the formula (III) and R 6 is a linear or branched alkyl or alkenyl group.

6. The viscosity index improver of claim 1 , wherein the compound (ii) is a compound of the formula (IV), and R 9 and R 11 are independently selected from a branched alkyl group and a branched alkenyl group.

7. The viscosity index improver of claim 1 , wherein the compound (ii) is a compound of the formula (V) and at least one of R 12 , R 13 , and R 14 is a branched alkyl group or branched alkenyl group, and at least one of R 15 , R 16 , and R 17 is a branched alkyl group or branched alkenyl group.

8. The viscosity index improver of claim 4 , wherein the at least one group that provides beta branching is a C 2 -C 17 alkyl or alkenyl group.

9. The viscosity index improver of claim 8 , wherein the compound (ii) is a primary amine.

10. The viscosity index improver of claim 4 , wherein the compound (ii) is a secondary amine and the at least one group that provides beta branching is a C 8 -C 18 alkyl or alkenyl group.

11. The viscosity index improver of claim 1 , wherein the compound (ii) is selected from 2-ethyl-1-hexylamine, 2-butyl-1-octylamine, 2-hexyl-1-decamine, 2-octyl-1-dodecylamine, 2-decyl-1-tetradecamine, 2-dodecyl-1-hexadecamine, and 2-tetradecyl-1-octadecamine.

12. The viscosity index improver of claim 1 , wherein the compound (ii) is selected from dioctylamine, 2-ethyl-1-hexylamine and bis(2-ethyl-1-hexyl)amine.

13. The viscosity index improver of claim 1 , wherein the compound (ii) is a compound of the Formulae (III)-(V) and one or more of R 7 , R 11 , and R 13 is a linear alkyl group or a linear alkenyl group attached to provide branching at a β carbon atom of the compound (ii).

14. The viscosity index improver of claim 1 , wherein the acylating agent is an ethylenically unsaturated acylating agent having at least one carboxylic acid or carboxylic anhydride group.

15. The viscosity index improver of claim 1 , wherein the acylating agent is at least one selected from the group consisting of maleic acid, fumaric acid, itaconic acid, citraconic acid, cyclohex-4-ene-1,2-di-carboxylic acid, bicyclo[2.21]hept-5-ene-2,3-dicarboxylic acid, maleic anhydride, itaconic anhydride, citraconic anhydride, allylsuccinic anhydride, 4-methylcyclohex-4-ene-1,2-dicarboxylic anhydride and bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride.

16. The viscosity index improver of claim 1 , wherein the acylating agent is maleic anhydride.

17. The viscosity index improver of claim 1 , wherein the ratio of moles of amine per mole of carboxyl groups of the acylated polymer, is from 0.5:1 to 2:1.

18. The viscosity index improver of claim 1 , wherein the acylated copolymer has acyl groups present in an amount of 0.3 weight percent to less than 30 weight percent, based on a total weight of the acylated copolymer.

19. The viscosity index improver of claim 1 , wherein the acylated copolymer has acyl groups present in an amount of 0.5 wt. % to 5 wt. %, based on a total weight of the acylated copolymer.

20. The viscosity index improver of claim 1 , wherein the acylated copolymer has 0.1 to 0.8 acyl groups per 1000 number average molecular weight units of the ethylene/C 3 -C 10 alpha-olefin copolymers.

21. The viscosity index improver of claim 1 , wherein the copolymer of ethylene and one or more C 3 -C 10 alpha-olefins has a polydispersity index of less than or equal to 4 and an average ethylene derived unit run length (n C2 ) which is less than 2.6, as determined by 13 C NMR spectroscopy, the average ethylene derived unit run length n c2 is defined as the total number of ethylene-derived units in the copolymer divided by a number of runs of one or more sequential ethylene-derived units in the copolymer, and the average ethylene derived unit run length n c2 also satisfies the relationship shown by the expression below:

n

C
⁢
2

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(

E
⁢
E
⁢
E

+

Assignees

• Afton Chemical Corp

Inventors

• Jiang Sheng
• Carranza Arturo

Classifications

• C10M143/04 Primary

  containing propene · CPC title

• C08F8/14 Primary

  Esterification · CPC title

• C10M161/00 Primary

  Lubricating compositions characterised by the additive being a mixture of a macromolecular compound and a non-macromolecular compound, each of these compounds being essential · CPC title

• C08F8/32

  by reaction with amines · CPC title

• C10N2030/08

  Resistance to extreme temperature · CPC title