Lubricant and fuel dispersants and methods of preparation thereof

Patent metadata

Field	Value
Publication number	US-10017708-B2
Application number	US-201314017651-A
Country	US
Kind code	B2
Filing date	Sep 4, 2013
Priority date	Sep 21, 2012
Publication date	Jul 10, 2018
Grant date	Jul 10, 2018

Abstract

This disclosure relates to a composition for use as an additive for fuels and lubricants including a reductive amination product of a vinyl terminated macromonomer (VTM) based aldehyde. Optionally aldehyde is reacted with the amino compound under condensation conditions sufficient to give an imine intermediate, and the imine intermediate is reacted under hydrogenation conditions sufficient to give the composition. The aldehyde is formed by reacting a VTM under hydroformylation conditions sufficient to form the aldehyde. A reductive amination method for making a composition for use as an additive for fuels and lubricants. The method includes reacting a VTM based aldehyde with an amino compound containing at least one —NH— group under condensation conditions sufficient to give an imine intermediate, and reacting the imine intermediate under hydrogenation conditions sufficient to give said composition. The aldehyde is formed by reacting a VTM under hydroformylation conditions sufficient to form the aldehyde.

First claim

What is claimed is:

1. A lubricant composition comprising:
an oil of lubricating viscosity, wherein the oil comprises a Group III or IV base oil stock, or mixtures thereof; and
from 0.1 to 15 weight percent based on the total weight of the lubricant composition of an additive comprising a vinyl terminated atactic polypropylene-based modified polyamine comprising less than 100ppm aluminum,
wherein the lubricant composition has a viscosity (Kv 100 ) from 2 to 8 cSt at 100° C., and a viscosity index (VI) from 100 to 160,
wherein the lubricant composition has a greater oxidation resistance as compared to oxidation resistance of a second lubricant composition containing an equal weight percent PIBSI (polyisobutylenesuccinimide), wherein the oxidation resistance is measured by HTE oxidation in hours to break; and
wherein the vinyl terminated atactic polypropylene-based modified polyamine is made by a process comprising: (i) hydroformylation or hydroformylation/hydrogenation of a VTM to make a VTM-based aldehyde or alcohol, followed by reductive amination, (ii) hydroformylation or hydroformylation/hydrogenation of a VTM to make a VTM-based aldehyde or alcohol, followed by reaction with an amine compound to obtain a Schiff's base or enamine, and then followed by hydrogenation of the Schiff's base or enamine, or (iii) a single step aminomethylation of a VTM with syngas and an amine compound to obtain an alkylamino substituted VTM.

2. The lubricant composition of claim 1 wherein the aldehyde is formed by reacting a VTM under hydroformylation conditions sufficient to give said aldehyde, and the alcohol is formed by reacting a VTM under hydroformylation conditions sufficient to give an aldehyde and reacting the aldehyde under hydrogenation conditions sufficient to give said alcohol.

3. The lubricant composition of claim 1 , wherein the vinyl terminated atactic polypropylene-based modified polyamine is made by a process comprising, in addition to steps in (i), (ii), or (iii), the following: (iv) reacting via additional formaldehyde coupling with a compound having antioxidant functionality to give a multifunctional composition having combined dispersant and antioxidant functionality, (v) reacting via additional formaldehyde coupling with a compound having anticorrosion functionality to give a multifunctional composition having combined dispersant and anticorrosion functionality, (vi) reacting via additional formaldehyde coupling with a compound having antiwear functionality to give a multifunctional composition having combined dispersant and antiwear functionality, or (vii) reacting with a boron containing compound to give a borated composition.

4. The lubricant composition of claim 1 which is a dispersant additive, a combined dispersant and antioxidant additive, a combined dispersant and viscosity index improver additive, a combined dispersant and anticorrosion additive, or a combined dispersant and antiwear additive.

5. The lubricant composition of claim 1 which possesses a lower viscosity (Kv 100 ) as compared to viscosity (Kv 100 ) of a same lubricating oil except containing PIBSI (polyisobutylenesuccinimide) as a dispersant on an equal weight percent basis.

6. The lubricant composition of claim 1 further comprising one or more of a viscosity improver, antioxidant, detergent, pour point depressant, corrosion inhibitor, metal deactivator, seal compatibility additive, anti-foam agent, inhibitor, and anti-rust additive.

7. The lubricant composition of claim 1 which is a passenger vehicle engine oil.

8. A vehicle having moving parts and containing a lubricant composition of claim 1 for lubricating the moving parts.

9. The lubricant composition of claim 1 , wherein the vinyl terminated atactic polypropylene-based modified polyamine is represented by the formula:
R 1 (X)R 3
wherein R 1 and R 3 , the same or different, are independent each a vinyl terminated atactic polypropylene group having from 10 to 400 carbon atoms, X is a polyamino group containing at least two —NH— groups, and R 3 is a vinyl terminated atactic polypropylene group having from 10 to 400 carbon atoms.

10. The lubricant composition of claim 1 wherein the vinyl terminated atactic polypropylene from which the atactic polypropylene-based modified polyamine is based has at least 93% ally chain ends and an isobutyl chain end to allylic vinyl group ratio of 0.8:1 to 1.35 to 1.

11. A dispersant additive for a lubricant composition, comprising a vinyl terminated macromonomer (VTM) modified polyamine made by a process comprising: (i) hydroformylation or hydroformylation/hydrogenation of a VTM to make a VTM-based aldehyde or alcohol, followed by reductive amination, (ii) hydroformylation or hydroformylation/hydrogenation of a VTM to make a VTM-based aldehyde or alcohol, followed by reaction with an amine compound to obtain a Schiff's base or enamine, and then followed by hydrogenation of the Schiff's base or enamine, or (iii) a single step aminomethylation of a VTM with syngas and an amine compound to obtain an alkylamino substituted VTM.

12. The dispersant additive of claim 11 , wherein the aldehyde is formed by reacting a VTM under hydroformylation conditions sufficient to give said aldehyde, and the alcohol is formed by reacting a VTM under hydroformylation conditions sufficient to give an aldehyde and reacting the aldehyde under hydrogenation conditions sufficient to give said alcohol.

13. The dispersant additive of claim 11 , wherein the vinyl terminated macromonomer (VTM) modified polyamine is made by a process comprising, in addition to steps in (i), (ii), or (iii), the following: (iv) reacting via additional formaldehyde coupling with a compound having antioxidant functionality to give a multifunctional composition having combined dispersant and antioxidant functionality, (v) reacting via additional formaldehyde coupling with a compound having anticorrosion functionality to give a multifunctional composition having combined dispersant and anticorrosion functionality, (vi) reacting via additional formaldehyde coupling with a compound having antiwear functionality to give a multifunctional composition having combined dispersant and antiwear functionality, or (vii) reacting with a boron containing compound to give a borated composition.

14. The dispersant additive of claim 13 , which is a combined dispersant and antioxidant additive, a combined dispersant and viscosity index improver additive, a combined dispersant and anticorrosion additive, or a combined dispersant and antiwear additive.

15. The dispersant additive of claim 11 , wherein the VTM is a vinyl-terminated polypropylene-based polyamine.

16. The dispersant additive of claim 11 , wherein the VTM comprises less than 100 ppm of aluminum.

17. The dispersant additive of claim 11 , wherein the VTM-modified polyamine is represented by the formula:
R 1 (X)R 3
wherein R 1 and R3 are independently each a vinyl terminated atactic polypropylene group having from 10 to 400 carbon atoms, X is a polyamino group containing at least two —NH— groups.

Assignees

• Exxonmobil Chemical Patents Inc

Inventors

• Patil Abhimanyu Onkar
• Chu John W
• Bodige Satish
• Farng Liehpao Oscar
• Crowther Donna Jean
• Ng Man Kit
• Brant Patrick
• Peretti Kathryn L

Classifications

• C10M2215/26

  Amines · CPC title

• C10L1/2283

  containing one or more carbon to nitrogen double bonds, e.g. guanidine, hydrazone, semi-carbazone, azomethine (C10L1/221, C10L1/226 take precedence) · CPC title

• C10N2030/10

  Inhibition of oxidation, e.g. anti-oxidants · CPC title

• C10M133/54 Primary

  Amines · CPC title

• C10M149/04 Primary

  containing monomers having an unsaturated radical bound to an amino group · CPC title