Viscosity improver grafted with unsaturated acylating agent and an aryloxyalylkene monoamine

Patent metadata

Field	Value
Publication number	US-9115237-B2
Application number	US-201213552545-A
Country	US
Kind code	B2
Filing date	Jul 18, 2012
Priority date	Jul 18, 2012
Publication date	Aug 25, 2015
Grant date	Aug 25, 2015

Abstract

Disclosed is an oil-soluble lubricating oil additive composition, suitable for use as a dispersant viscosity index improver in lubricating oils; prepared by the process which comprises reacting a hydrocarbon polymer having a number average molecular weight (M n ) between about 7,000 and about 500,000 wherein the polymer backbone has been functionalized with an ethylenically unsaturated acylating agent and an aryloxy-alkylene amine.

First claim

What is claimed is:

1. An oil-soluble lubricating oil additive composition prepared by the process which comprises reacting:
(a) a hydrocarbon polymer having a number average molecular weight (M n ) between about 7,000 and about 500,000:
(b) an ethylenically unsaturated acylating agent; and
(c) an aryloxy-alkylene amine is of the formula Ar—O-Alk-NH 2 wherein Ar is an aromatic moiety selected from benzene, naphthylene or anthracene or optionally substituted benzene, optionally substituted naphthylene or optionally, substituted anthracene, wherein the optionally substituted groups are selected from 1 to 3 substituent groups selected from alkyl, alkenyl, alkoxy, aryl, alkaryl, arylalkyl, aryloxy, wherein alkyl is straight or branched chain carbon having 6 carbon atoms or less; and -Alk- comprises straight and branched chain alkylene groups having 1 to 10 carbon atoms, which may optionally be substituted with a group consisting of phenyl and benzyl.

2. The oil-soluble lubricating oil additive of claim 1 , wherein the hydrocarbon polymer is a homopolymer or copolymer selected from the group consisting of: (1) polymers of aliphatic olefins having from 2 to about 28 carbon atoms; (2) polymers of dienes; (3) copolymers of conjugated dienes with vinyl substituted aromatic compounds; and (4) star polymers.

3. The oil-soluble lubricating oil additive of claim 2 , wherein the copolymer selected from (1) polymers of aliphatic olefins having from 2 to about 28 carbon atoms wherein one olefin is ethylene.

4. The oil-soluble lubricating oil additive of claim 3 , wherein the ethylene content of the copolymer is from 45-52 wt % ethylene.

5. The oil-soluble lubricating oil additive of claim 4 , wherein the copolymer is an ethylene-propylene copolymer having a number average molecular weight from 7,000 to about 60,000.

6. The oil-soluble lubricating oil additive of claim 2 , wherein the hydrocarbon polymer is an optionally hydrogenated polymer of dienes, wherein the diene is a conjugated diene selected from the group consisting of isoprene, butadiene, and piperylene.

7. The oil-soluble lubricating oil additive of claim 2 , wherein the hydrocarbon polymer is an optionally hydrogenated copolymer of a conjugated diene with vinyl substituted aromatic compound wherein the vinyl substituted aromatic compound is a styrenic monomer.

8. The oil-soluble lubricating oil additive of claim 7 , wherein the diene is selected from the group consisting of isoprene and 1,3-butadiene.

9. The oil-soluble lubricating oil additive of claim 2 , wherein the hydrocarbon polymer is a star polymer wherein the arms are derived from dienes and vinyl substituted aromatic compounds.

10. The oil-soluble lubricating oil additive of claim 1 , wherein the ethylenically unsaturated carboxylic acid or functional derivative thereof, comprises at least one member of the group consisting of acrylic acid, crotonic acid, methyacrylic acid, maleic acid, maleic anhydride, fumaric acid, itaconic acid and itaconic anhydride, citraconic acid, citraconic anhydride, mesaconic acid, glutaconic acid, chloromaleic acid, aconitic acid, methylcrotonic acid, sorbic acid, and ester of the acids, and combinations of the foregoing.

11. The oil-soluble lubricating oil additive of claim 1 , wherein grafting of the hydrocarbon copolymer is conducted at about 100° C. to about 250° C. in the presence of a free radical initiator.

12. The oil-soluble lubricating oil additive of claim 11 , wherein the hydrocarbon polymer backbone has been functionalized with a maleic anhydride acylating agent in the range of 0.5 to 3.0 wt % of Maleic anhydride based upon the total mass of polymer.

13. The oil-soluble lubricating oil additive of claim 1 , wherein the ethylenically unsaturated carboxylic acid or, functional derivative thereof is first reacted with the aryloxy-alkylene amine to form a reaction product wherein the reaction product is grafted to the polymer backbone.

14. The oil-soluble lubricating oil additive of claim 1 , wherein the aryloxy-alkylene amine is of the formula Ar—O-Alk-NH 2 is selected herein Ar is an aromatic moiety selected from benzene, naphthylene and anthracene.

15. The aryloxy-alkyene amine of claim 14 , wherein Ar is selected from naphthylene and anthracene.

16. The oil-soluble lubricating oil additive of claim 1 , wherein the aryloxy-alkylene amine is of the formula Ar—O-Alk-NH 2 is selected wherein Ar is an aromatic moiety contains at least two aromatic groups either fused or linked by a carbon to carbon bond, alkylene linkage, ether linkage, ester linkage, or keto linkage.

17. The oil-soluble lubricating oil additive of claim 1 , wherein the aryloxy-alkylene amine is of the formula Ar—O-Alk-NH 2 is selected wherein Ar is an substituted aromatic moiety selected from group consisting of substituted benzene, substituted naphthylene and substituted anthracene, wherein the substituted groups selected from 1 to 3 substituent groups selected from alkyl, alkoxy, aryl, alkaryl, arylalkyl, aryloxy, wherein alkyl is straight or branched chain carbon having 1 to 6 carbon atoms.

18. The aryloxy-alkylene amine of claim 17 , wherein the Ar has a single substituent group selected from aryl, alkaryl, arylalkyl, and aryloxy.

19. The oil-soluble lubricating oil additive of claim 1 , wherein the aryloxy-alkylene amine is of the formula Ar—O-Alk-NH 2 is selected wherein Alk is —CH 2 CH(R o )— wherein R o is selected from the group consisting of hydrogen, a straight or branched chain alkyl group having 1 to 6 carbon atoms, aryl and arylalkyl.

20. The oil-soluble lubricating oil additive of claim 1 , wherein the aryloxy-alkylene amine is of the formula Ar—O-Alk-NH 2 is selected wherein Alk is selected from the group —CH 2 CH 2 —, —CH 2 CH 2 (CH 3 )—, —CH 2 CH 2 CH 2 —, and —CH 2 CH 2 (CH 3 )CH 2 —.

21. An additive concentrate comprising an inert liquid organic diluent and from about 3 to 50 percent by weight of the oil soluble lubricating oil additive of claim 1 .

22. The additive concentrate of claim 21 , wherein the inert liquid organic diluent is a diluent oil selected from a Group II, Group III Group IV or Group V base oil or a mixture thereof, or a mixture of a Group I base oil and at least one Group II, Group II or Group IV base oil.

23. A lubricating oil composition comprising a major amount of an oil of lubricating viscosity and a minor amount of the oil soluble lubricating oil additive of claim 1 .

24. The lubricating oil composition of claim 23 , further comprising at least one additive selected from the group consisting of antioxidants, antiwear agents, detergents, dispersants, friction modifiers, corrosion and rust inhibitors, viscosity index improvers and anti-foam agents.

25. The lubricating oil composition of claim 24 , wherein the at least one additives are selected for use as a heavy duty diesel engine lubricating oil composition.

Assignees

• Mcdougall Patrick J
• Patel Pritesh A
• Chevron Oronite Co

Inventors

• Mcdougall Patrick J
• Patel Pritesh A

Classifications

• C10M2217/024

  containing monomers having an unsaturated radical bound to an amido or imido group · CPC title

• C10M149/06

  containing monomers having an unsaturated radical bound to an amido or imido group · CPC title

• C08F8/32

  by reaction with amines · CPC title

• C10N2020/04

  Molecular weight; Molecular weight distribution · CPC title

• C10M2217/04

  Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds · CPC title