Polyimide dispersants and methods of making and using thereof

Patent metadata

Field	Value
Publication number	US-11274181-B2
Application number	US-201816134504-A
Country	US
Kind code	B2
Filing date	Sep 18, 2018
Priority date	Sep 18, 2017
Publication date	Mar 15, 2022
Grant date	Mar 15, 2022

Abstract

Provided herein are polyimide dispersants, as well as methods for producing polyimide dispersants. The polyimides can be defined by the formula below

wherein A, individually for each occurrence, represents a cyclic diimide moiety represented by the structure below

where B represents a cyclic moiety substituted with a first cyclic imide group and a second cyclic imide group; Y, individually for each occurrence, represents a bivalent linking group; L, individually for each occurrence, is absent or represents a cyclic imide group; R, individually for each occurrence, represents a polymeric tail; and n is an integer from 1 to 20.

First claim

What is claimed is:

1. A polyimide compound defined by Formula I below

wherein
A, individually for each occurrence, represents a cyclic diimide moiety represented by the structure below

where B represents a cyclic moiety substituted with a first cyclic imide group and a second cyclic imide group;
Y, individually for each occurrence, represents a bivalent linking group;
L, individually for each occurrence, is absent or represents a cyclic imide group;
R, individually for each occurrence, represents a polymeric tail; and
n is an integer from 1 to 20.

2. The compound of claim 1 , wherein Y is, individually for each occurrence, chosen from alkylene, heteroalkylene, cycloalkylene, heterocycloalkylene, arylene, heteroarylene, alkylarylene, alkylheteroarylene, polyalkyleneoxy, or polyalkenylamino.

3. The compound of claim 1 , wherein Y is, individually for each occurrence, comprises from 2 to 30 carbon atoms.

4. The compound of claim 1 , wherein B comprises an aryl group.

5. The compound of claim 1 , wherein the first cyclic imide group comprises a five-membered cyclic imide ring and the second cyclic imide group comprises a five-membered cyclic imide ring.

6. The compound of claim 5 , wherein A is chosen from one of the following

wherein
X is absent, or represents

polyalkyleneoxy, or polyalkenylamino;
R 1 represents, independently for each occurrence, H, halogen, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, alkoxy, aryl, heteroaryl, alkylaryl, or alkylheteroaryl, or wherein permissible, two adjacent R 1 groups, together with the atoms to which they are attached, form a 5-8 membered substituted or unsubstituted aromatic or non-aromatic ring;
R 2 and R 3 represent, independently for each occurrence, H, halogen, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, alkoxy, aryl, heteroaryl, alkylaryl, or alkylheteroaryl;
Ar represents an aryl group; and
m is an integer from 1 to 12.

7. The compound of claim 1 , wherein the first cyclic imide group comprises a six-membered cyclic imide ring and the second cyclic imide group comprises a six-membered cyclic imide ring.

8. The compound of claim 7 , wherein A is chosen from one of the following

wherein
X is absent, or represent

polyalkyleneoxy, or polyalkenylamino;
R 1 represents, independently for each occurrence, H, halogen, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, alkoxy, aryl, heteroaryl, alkylaryl, or alkylheteroaryl, or wherein permissible, two adjacent R 1 groups, together with the atoms to which they are attached, form a 5-8 membered substituted or unsubstituted aromatic or non-aromatic ring;
R 2 and R 3 represent, independently for each occurrence, H, halogen, alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, alkoxy, aryl, heteroaryl, alkylaryl, or alkylheteroaryl;
Ar represents an aryl group; and
m is an integer from 1 to 12.

9. The compound of claim 1 , wherein n is an integer from 1-6.

10. The compound of claim 1 , wherein R is a hydrophobic moiety.

11. The compound of claim 1 , wherein R is chosen from a polyolefin group, a polyetheramine group; a polyalkenylamine group; a polyalkyleneoxy group, or a combination thereof.

12. The compound of claim 1 , wherein R comprises a polyolefin group terminated by an initiator residue.

13. The compound of claim 1 , wherein R comprises a polyisobutylene group terminated by an initiator residue.

14. The compound of claim 1 , wherein L is absent.

15. The compound of claim 14 , where the compound is defined by Formula IA below
R x —R a —Y- A-Y n —R a —R x   Formula IA

wherein
A and n are as defined above with respect to Formula I,
R x is an initiator residue; and
R a is a polyolefin group.

16. The compound of claim 1 , where the compound is defined by Formula IB below

wherein
A, Y, and n are as defined above with respect to Formula I,
R x is an initiator residue; and
R a is a polyolefin group.

17. The compound of claim 16 , wherein R a comprises a polyisobutylene group.

18. The compound of claim 1 , wherein n is 1.

19. The compound of claim 1 , wherein the compound is a dispersant for use in lubricating oils and R has a molecular weight of from 1,000 Da to 2,500 Da.

20. The compound of claim 1 , wherein the compound is an additive for use in a hydrocarbon fuel and R has a molecular weight of less than 1,000 Da.

Assignees

• Chevron Oronite Co

Inventors

• Morgan David
• Ma Roland
• Masson Georgeta

Classifications

• C10M133/56 Primary

  Amides; Imides · CPC title

• C10L2200/0446

  Diesel · CPC title

• C10L1/238

  obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds {(C10L1/221 takes precedence)} · CPC title

• C10L10/18

  use of detergents or dispersants for purposes not provided for in groups C10L10/02 - C10L10/16 · CPC title

• C10N2030/04

  Detergent property or dispersant property · CPC title