Polyolefin-substituted amines grafted with poly(aromatic-N-monomers) for oleaginous compositions

• US 5,633,326 A
• Filed: 06/26/1996
• Issued: 05/27/1997
• Est. Priority Date: 12/13/1989
• Status: Expired due to Fees

• Current Assignee: Exxon Chemical Patents Inc. (Exxon Mobil Corporation)
• Original Assignee: Exxon Chemical Patents Inc. (Exxon Mobil Corporation)
• Inventors: Patil, Abhimanyu O., Gutierrez, Antonio, Lundberg, Robert D.
• Primary Examiner(s): Lipman, Bernard
• Application Number:
  US08/668,313
• Time in Patent Office: 335 Days
• Field of Search: 525/327.6, 525/329.6, 525/329.9, 525/330.5
• US Class Current: 525/327.6
• CPC Class Codes: C08F 110/06 Propene
• CPC Class Codes: C08F 110/10 Isobutene
• CPC Class Codes: C08F 271/00 Macromolecular compounds obtained by polymerising monomers on to polymers of nitrogen-containing monomers as defined in group C08F26/00
• CPC Class Codes: C08F 2800/10 as molar percentages
• CPC Class Codes: C08F 8/20 Halogenation
• CPC Class Codes: C08F 8/32 by reaction with amines
• CPC Class Codes: C08F 8/42 Introducing metal atoms or metal-containing groups
• CPC Class Codes: C08F 8/46 Reaction with unsaturated dicarboxylic acids or anhydrides thereof, e.g. maleinisation
• CPC Class Codes: C10L 1/221 compounds of uncertain formula; reaction products where mixtures of compounds are obtained
• CPC Class Codes: C10L 1/238 obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds C10L1/221 takes precedence
• CPC Class Codes: C10L 1/2475 obtained otherwise than by reactions only involving unsaturated carbon to carbon bonds
• CPC Class Codes: C10L 1/303 boron compounds
• CPC Class Codes: C10L 10/04 for minimising corrosion or incrustation
• CPC Class Codes: C10M 133/54 Amines
• CPC Class Codes: C10M 143/00 Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
• CPC Class Codes: C10M 143/12 containing conjugated diene
• CPC Class Codes: C10M 149/00 Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
• CPC Class Codes: C10M 159/12 Reaction products
• CPC Class Codes: C10M 159/16 obtained by Mannich reactions
• CPC Class Codes: C10M 2205/00 Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
• CPC Class Codes: C10M 2205/02 : containing acyclic monomers
• CPC Class Codes: C10M 2215/04 : having amino groups bound to acyclic or cycloaliphatic carbon atoms
• CPC Class Codes: C10M 2215/042 : containing hydroxy groups; Alkoxylated derivatives thereof
• CPC Class Codes: C10M 2215/26 : Amines
• CPC Class Codes: C10M 2217/00 : Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
• CPC Class Codes: C10M 2217/02 : Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C10M 2217/04 : Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C10M 2217/042 : between the nitrogen-containing monomer and an aldehyde or ketone
• CPC Class Codes: C10M 2217/043 : Mannich bases
• CPC Class Codes: C10M 2217/046 : Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
• CPC Class Codes: C10M 2217/06 : Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
• CPC Class Codes: C10M 2227/00 : Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions

Abstract

Novel polymers comprising polyolefin-substituted amines grafted with aromatic N-containing monomers such as aniline, have been found to provide oil soluble polymers having dispersant and antioxidant properties in oleaginous compositions, including fuel and lubricating oils. The polymers of this invention are further useful in electrical applications. These materials are formed by a process which comprises: (a) contacting an amine compound having at least two reactive nitrogen moieties with at least one long chain hydrocarbon-substituted reactant in an amount and under conditions sufficient to form a N-containing polymer adduct containing reactive amine groups, and (b) contacting the N-containing polymer adduct with at least one aromatic N-containing monomer under polymerization conditions to graft said N-containing polymer adduct with aromatic N-containing polymer segments. The long chain hydrocarbon-substituted reactant can comprise materials such as (i) long chain hydrocarbons substituted with mono- or dicarboxylic acid, anhydride or ester groups; (ii) halogenated long chain hydrocarbons; (iii) mixtures of formaldehyde and a long chain hydrocarbyl substituted phenol; and (iv) mixtures of formaldehyde and a reaction product formed by reaction of long chain hydrocarbons substituted with mono- or dicarboxylic acid, anhydride or ester groups and an amino-substituted, optionally hydrocarbyl-substituted phenol.

Claims

1. An oil-soluble dispersant and antioxidant additive which comprises an N-containing polymer adduct comprising the reaction product of a polyalkylene polyamine with a polymer substituted with mono- or dicarboxylic acid, anhydride or ester groups, wherein said N-containing polymer adduct has been grafted in the presence of an effective amount of an oxidizing agent, by polymerizing thereon at least one aromatic N-monomer represented by the formula:

space="preserve" listing-type="equation">Ar'"'"'[NH(R.sup.b)]y'"'"'

wherein Ar'"'"' is ##STR15## wherein R^c in each instance in which it appears is independently C₁ to C₁₂ alkyl, y'"'"' is an integer of from 1 to 4, y" is an integer of from 0 to 4, y"'"'"' is an integer of from 0 to 4, D in each instance in which it appears is independently Cl, Br or I, R^b is hydrogen or C₁ to C₂₀ alkyl, and Z¹ is a branched or straight chain alkylene group which can contain one or more --O-- or --S-- chain atoms, with the proviso that the sum of y'"'"'+y"+y"'"'"' is from 1 to 5.

2. The oil-soluble additive according to claim 1 wherein said substituted polymer reactant comprises at least one long chain hydrocarbyl substituted mono- or dicarboxylic acid producing material formed by reacting (i) an olefin polymer derived from C₂ to C₁₀ monoolefin and having a number average molecular weight of about 300 to 10,000 and (ii) at least one of a C₄ to C₁₀ monounsaturated dicarboxylic acid material and a C₃ to C₁₀ monounsaturated monocarboxylic acid material, having an average of at least about 0.5 dicarboxylic acid producing moieties, per molecule of said olefin polymer present in the reaction mixture used to form said acid producing material.

3. The oil-soluble additive according to claim 2 wherein in said polyalkylene polyamine each said alkylene group contains from 2 to 6 carbons and said polyalkylene polyamine contains from 3 to about 8 nitrogen atoms per molecule.

4. The oil-soluble additive according to claim 3, wherein said hydrocarbyl substituted monounsaturated acid producing material comprises hydrocarbyl substituted C₄ to C₁₀ monounsaturated dicarboxylic acid producing material which comprises polyisobutylene of about 700 to 5000 number average molecular weight substituted with succinic anhydride moieties and wherein in said polyalkylene polyamine each said alkylene group contains from 2 to 6 carbons and said polyalkylene polyamine contains from 5 to 9 nitrogen atoms per molecule.

5. The oil-soluble additive according to claim 4, wherein said polyalkylene polyamine comprises polyethylene polyamine or polypropyleneamine.

6. The oil-soluble additive of claim 5, wherein said number average molecular weight of said polyisobutylene is from about 1,300 to 3,000.

7. The oil-soluble additive of claim 6, wherein said monounsaturated acid material comprises maleic anhydride.

8. The oil soluble additive of claim 1 wherein said polymer comprises ethylene-propylene copolymer.

9. The oil soluble additive of claim 8 wherein said copolymer number average molecular weight is from about 3,000 to 10,000.

10. The oil soluble additive of claim 1, wherein said aromatic monomer comprises at least one member selected from the group consisting of aniline, o-toluidine, m-toluidine, o-ethylaniline, and m-ethylaniline.