Polyolefin-derived dispersants

Patent metadata

Field	Value
Publication number	US-10584297-B2
Application number	US-201615377788-A
Country	US
Kind code	B2
Filing date	Dec 13, 2016
Priority date	Dec 13, 2016
Publication date	Mar 10, 2020
Grant date	Mar 10, 2020

Abstract

Ethylene-C3-C10 alpha olefin copolymers, dispersants and lubricating oils/fuel compositions incorporating dispersants, and related methods are generally described herein. The copolymer may comprise ethylene-derived units and C3-C10 alpha-olefin-derived units. The C3-C10 alpha-olefin-derived units may have a carbon number from three to ten. For example, the C3-C10 alpha-olefin-derived units may be propylene-derived units.

First claim

What is claimed is:

1. A dispersant prepared by a process comprising: functionalizing a copolymer derived from ethylene and propylene,
wherein the copolymer has a number average molecular weight of less than 4,000 g/mol as measured by GPC;
wherein at least 30% and less than 65% of the total number of units in the copolymer are ethylene-derived units;
wherein 70 mol % or greater of the copolymer has a carbon-carbon double bond in a terminal monomer unit, and at least 70 mol % of the terminal monomer units that have a carbon-carbon double bond have a terminal group selected from a vinylidene group and a tri-substituted isomer of a vinylidene group, wherein the vinylidene group and the tri-substituted isomer of a vinylidene group of the copolymer have one or more of the following structural formulas (A)-(B):

wherein R represents a methyl group and

indicates a bond attached to the remaining portion of the copolymer;
wherein the copolymer has an average ethylene-derived unit run length n c2 , as determined by 13 C NMR spectroscopy, of less than 2.6, 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

<

(

EEE
+
EEA
+
AEA

)

(

AEA
+

0.5
⁢
EEA

)

wherein:
EEE=(x C2 ) 3 ,
EEA=2(x C2 ) 2 (1−x C2 ),
AEA=x C2 (1−x C2 ) 2 ,

x C2 being the mole fraction of ethylene incorporated in the copolymer as measured by 1 H-NMR spectroscopy, E representing an ethylene unit, and A representing a propylene unit, and
wherein the copolymer has a crossover temperature of −25° C. or lower.

2. The dispersant of claim 1 , wherein the copolymer has a crossover temperature of −35° C. or lower.

3. The dispersant of claim 1 , wherein at least 30% and less than 60% of the total number of units in the copolymer are ethylene-derived units.

4. The dispersant of claim 1 , wherein at least 30% and less than 50% of the total number of units in the copolymer are ethylene-derived units.

5. The dispersant of claim 1 , wherein at least 85 mol % of the unsaturation is the terminal vinylidene group and the terminal tri-substituted isomer of a vinylidene group.

6. The dispersant of claim 1 , wherein at least 95 mol % of the unsaturation is the terminal vinylidene group and the terminal tri-substituted isomer of a vinylidene group.

7. The dispersant of claim 1 , wherein the copolymer has an average ethylene run length of less than 2.4.

8. The dispersant of claim 1 , wherein the copolymer has an average ethylene run length of less than 2.2.

9. The dispersant of claim 1 , wherein the copolymer has a polydispersity index of less than or equal to 4.

10. The dispersant of claim 1 , wherein the copolymer has a polydispersity index of less than or equal to 3.

11. The dispersant of claim 1 , wherein the ethylene content is 40-60 mol % and the propylene content is 40-60 mol %.

12. The dispersant of claim 1 , wherein the ethylene content is about 40-50 mol % and the propylene content is about 50-60 mol %.

13. The dispersant of claim 1 , wherein the number average molecular weight of the copolymer is less than 2,500 g/mol, as measured by GPC.

14. The dispersant of claim 1 , wherein the number average molecular weight of the copolymer is less than 1,500 g/mol, as measured by GPC.

15. The dispersant of claim 1 , wherein the dispersant is post-treated.

16. The dispersant of claim 1 , wherein the dispersant is posted treated with anhydride, a boron compound, or a mixture thereof.

17. The dispersant of claim 1 , wherein the dispersant has one of the following formulas:

wherein R 1 is an hydrocarbyl radical derived from the copolymer; R 2 is a divalent C 1 -C 6 alkylene; R 3 is a divalent C 1 -C 6 alkylene; each of R 4 and R 5 , independently, is H, C 1 -C 6 alkyl,

or, together with the N to which they are attached to, form a 5 or 6-membered ring optionally fused with an aromatic or non-aromatic ring; R 6 is H or C 1 -C 6 alkyl, or —CH 2 —(NH—R 2 ) n —NR 4 R 5 ; Y is a covalent bond or C(O); and n is 0, 1, 2, 3, 4, 5, 6, 7, or 8.

18. A lubricating oil, comprising:
at least 50 wt % of a base oil;
3-20 wt % of a viscosity index improver;
0-1 wt % of a pour point depressant; and
0.2-20 wt % of the dispersant of claim 1 .

19. The lubricating oil of claim 18 , wherein the lubricating oil has a mini-rotary viscometer (MRV) value of 60,000 cP or less at −30° C. as determined by the ASTM D4684 test.

20. The lubricating oil of claim 18 , wherein the lubricating oil has a mini-rotary viscometer (MRV) value of 60,000 cP or less at −40° C. as determined by the ASTM D4684 test.

21. The lubricating oil of claim 18 , wherein the lubricating oil contains less than 10 wt % of the dispersant.

22. A lubricating additive package comprising:
30-80 wt % of the dispersant of claim 1 .

23. A fuel composition or fuel additive composition, comprising the dispersant of claim 17 .

24. The fuel composition or fuel additive composition of claim 23 , the dispersant having one of the following formulas:

wherein R 1 is an hydrocarbyl radical derived from the copolymer; R 2 is a divalent C 1 -C 6 alkylene; R 3 is a divalent C 1 -C 6 alkylene; each of R 4 and R 5 , independently, is H, C 1 -C 6 alkyl,

or, together with the N to which they are attached to, form a 5 or 6-membered ring optionally fused with an aromatic or non-aromatic ring; R 6 is H or C 1 -C 6 alkyl, or —CH 2 —(NH—R 2 ) n —NR 4 R 5 ; Y is a covalent bond or C(O); and n is 0, 1, 2, 3, 4, 5, 6, 7, or 8.

Assignees

• Afton Chemical Corp

Inventors

• Cain Nathaniel
• Loper John T
• Cunningham Lawrence
• Roos Joseph W

Classifications

• C10N2070/02

  Concentrating of additives · CPC title

• C10N2060/14

  by boron or a compound containing boron · CPC title

• C10N2060/00

  Chemical after-treatment of the constituents of the lubricating composition · CPC title

• C10N2040/255

  Gasoline engines · CPC title

• C10N2040/252

  Diesel engines · CPC title