Derivatives of polyamines with one primary amine and secondary of tertiary amines

• US 5,643,859 A
• Filed: 06/17/1994
• Issued: 07/01/1997
• Est. Priority Date: 12/17/1992
• Status: Expired due to Fees

• Current Assignee: Exxon Chemical Patents Inc. (Exxon Mobil Corporation)
• Original Assignee: Exxon Chemical Patents Inc. (Exxon Mobil Corporation)
• Inventors: Stokes, James P., Gutierrez, Antonio, Gorda, Keith R., Dankworth, David C., Eckstrom, William B., Emert, Jacob I., Cusumano, Joseph V., Thaler, Warren A., Diana, William D.
• Primary Examiner(s): Barts, Samuel
• Application Number:
  US08/261,534
• Time in Patent Office: 1,110 Days
• Field of Search: 252/9, 508/443, 508/454, 508/478, 508/508, 44/383, 44/386
• US Class Current: 508/454
• CPC Class Codes: B01J 19/2415 Tubular reactors
• CPC Class Codes: B01J 19/242 in series
• CPC Class Codes: B01J 2219/00094 Jackets
• CPC Class Codes: C07C 51/14 on a carbon-to-carbon unsaturated bond in organic compounds
• CPC Class Codes: C07C 67/38 by addition to an unsaturated carbon-to-carbon bond
• CPC Class Codes: C07C 69/52 Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
• CPC Class Codes: C08F 10/08 Butenes
• CPC Class Codes: C08F 110/08 Butenes
• CPC Class Codes: C08F 210/06 Propene
• CPC Class Codes: C08F 210/08 Butenes
• CPC Class Codes: C08F 210/16 Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
• CPC Class Codes: C08F 2800/20 as weight or mass percentages
• CPC Class Codes: C08F 8/00 Chemical modification by after-treatment graft polymers, block polymers, crosslinking with unsaturated monomers or with polymers C08F251/00 - C08F299/00; of conjugated diene rubbers C08C
• CPC Class Codes: C08F 8/14 Esterification
• CPC Class Codes: C08F 8/18 Introducing halogen atoms or halogen-containing groups
• 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: C10L 1/143 mixtures of organic macromolecular compounds with organic non-macromolecular compounds
• CPC Class Codes: C10L 1/1817 Compounds of uncertain formula; reaction products where mixtures of compounds are obtained
• CPC Class Codes: C10L 1/195 obtained by reactions involving only carbon-to-carbon unsaturated bonds
• CPC Class Codes: C10L 1/198 : obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
• CPC Class Codes: C10L 1/206 : macromolecular compounds
• CPC Class Codes: C10L 1/208 : containing halogen, oxygen, with or without hydrogen
• CPC Class Codes: C10L 1/221 : compounds of uncertain formula; reaction products where mixtures of compounds are obtained
• CPC Class Codes: C10L 1/236 : obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof C10L1/221 takes precedence
• 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 1/2383 : Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C) C10L1/221 takes precedence
• CPC Class Codes: C10L 1/2387 : Polyoxyalkyleneamines (poly)oxyalkylene amines and derivatives thereof (substituted by a macromolecular group containing 30C) 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 1/2493 : compounds of uncertain formula; reactions of organic compounds (hydrocarbons, acids, esters) with sulfur or sulfur containing compounds
• CPC Class Codes: C10L 1/2683 : obtained otherwise than by reactions only involving unsaturated carbon to carbon bonds
• CPC Class Codes: C10L 1/2691 : Compounds of uncertain formula; reaction of organic compounds (hydrocarbons acids, esters) with Px Sy, Px Sy Halz or sulfur and phosphorus containing compounds
• CPC Class Codes: C10L 1/285 : macromolecular compounds
• CPC Class Codes: C10L 1/30 : compounds not mentioned before (complexes)
• CPC Class Codes: C10L 1/303 : boron compounds
• CPC Class Codes: C10L 10/18 : use of detergents or dispersants for purposes not provided for in groups C10L10/02 - C10L10/16
• CPC Class Codes: C10M 129/95 : Esters
• CPC Class Codes: C10M 133/06 : having amino groups bound to acyclic or cycloaliphatic carbon atoms
• CPC Class Codes: C10M 133/52 : having a carbon chain of 30 or more atoms
• CPC Class Codes: C10M 133/54 : Amines
• CPC Class Codes: C10M 133/56 : Amides; Imides
• 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 145/12 : monocarboxylic
• CPC Class Codes: C10M 149/06 : containing monomers having an unsaturated radical bound to an amido or imido group
• CPC Class Codes: C10M 159/18 : Complexes with metals
• CPC Class Codes: C10M 2207/023 : having hydroxy groups bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C10M 2207/281 : of (cyclo)aliphatic monocarboxylic acids
• CPC Class Codes: C10M 2207/282 : of (cyclo)aliphatic oolycarboxylic acids
• CPC Class Codes: C10M 2207/283 : of polyhydroxy compounds
• CPC Class Codes: C10M 2207/286 : of polymerised unsaturated acids
• CPC Class Codes: C10M 2207/289 : containing free hydroxy groups
• CPC Class Codes: C10M 2209/00 : Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions oxidised hydrocarbons C10M2205/12
• CPC Class Codes: C10M 2209/02 : Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C10M 2209/082 : monocarboxylic
• CPC Class Codes: C10M 2209/10 : Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• 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 2215/08 : Amides
• CPC Class Codes: C10M 2215/082 : containing hydroxyl groups; Alkoxylated derivatives
• CPC Class Codes: C10M 2215/22 : Heterocyclic nitrogen compounds
• CPC Class Codes: C10M 2215/221 : Six-membered rings containing nitrogen and carbon only
• CPC Class Codes: C10M 2215/224 : Imidazoles
• CPC Class Codes: C10M 2215/225 : the rings containing both nitrogen and oxygen
• CPC Class Codes: C10M 2215/226 : Morpholines
• CPC Class Codes: C10M 2215/26 : Amines
• CPC Class Codes: C10M 2215/28 : Amides; Imides
• CPC Class Codes: C10M 2215/30 : Heterocyclic compounds
• CPC Class Codes: C10M 2217/024 : containing monomers having an unsaturated radical bound to an amido or imido group
• 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 2219/062 : having carbon-to-sulfur double bonds
• CPC Class Codes: C10M 2227/061 : Esters derived from boron
• CPC Class Codes: C10M 2227/09 : Complexes with metals
• CPC Class Codes: C10N 2010/02 : Groups 1 or 11
• CPC Class Codes: C10N 2010/04 : Groups 2 or 12
• CPC Class Codes: C10N 2010/06 : Groups 3 or 13
• CPC Class Codes: C10N 2010/08 : Groups 4 or 14
• CPC Class Codes: C10N 2010/10 : Groups 5 or 15
• CPC Class Codes: C10N 2010/12 : Groups 6 or 16
• CPC Class Codes: C10N 2010/14 : Group 7
• CPC Class Codes: C10N 2040/00 : Specified use or application for which the lubricating composition is intended
• CPC Class Codes: C10N 2040/02 : Bearings
• CPC Class Codes: C10N 2040/04 : Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
• CPC Class Codes: C10N 2040/042 : for automatic transmissions
• CPC Class Codes: C10N 2040/044 : for manual transmissions
• CPC Class Codes: C10N 2040/046 : for traction drives
• CPC Class Codes: C10N 2040/08 : Hydraulic fluids, e.g. brake-fluids
• CPC Class Codes: C10N 2040/20 : Metal working
• CPC Class Codes: C10N 2040/25 : Internal-combustion engines
• CPC Class Codes: C10N 2040/251 : Alcohol fueled engines
• CPC Class Codes: C10N 2040/252 : Diesel engines
• CPC Class Codes: C10N 2040/253 : Small diesel engines
• CPC Class Codes: C10N 2040/255 : Gasoline engines
• CPC Class Codes: C10N 2040/26 : Two-strokes or two-cycle engines
• CPC Class Codes: C10N 2040/28 : Rotary engines
• CPC Class Codes: C10N 2040/30 : Refrigerators lubricants or compressors lubricants
• CPC Class Codes: C10N 2040/32 : Wires, ropes or cables lubricants
• CPC Class Codes: C10N 2040/34 : Lubricating-sealants
• CPC Class Codes: C10N 2040/36 : Release agents or mold release agents
• CPC Class Codes: C10N 2040/38 : Conveyors or chain belts
• CPC Class Codes: C10N 2040/40 : Generators or electric motors in oil or gas winning field
• CPC Class Codes: C10N 2040/42 : Flashing oils or marking oils
• CPC Class Codes: C10N 2040/44 : Super vacuum or supercritical use
• CPC Class Codes: C10N 2040/50 : Medical uses
• CPC Class Codes: C10N 2070/02 : Concentrating of additives

Abstract

A dispersant derivatized from a functionalized hydrocarbon and a polyamine having one primary amine and 1-10, preferably 3-8 secondary or tertiary amines; preferably where said functionalized hydrocarbon is a Koch-derived hydrocarbon.

Claims

1. A dispersant comprising a functionalized hydrocarbon polymer derivatized by reaction with a polyamine having one primary amino group and 1 to 10 secondary or tertiary amino groups, wherein the hydrocarbon polymer is other than gem-structured polyolefin and has a number average molecular weight of at least 500 and the functionalized hydrocarbon polymer is functionalized by direct attachment of groups of the formula --CO--Y--R³, wherein Y is O or S and R³ is either (i) H or hydrocarbyl and at least about 50 mole percent of the functional groups --CO--Y--R³ are attached to a tertiary carbon atom of the polymer backbone or (ii) aryl, substituted aryl, or substituted hydrocarbyl.

2. The dispersant according to claim 1, wherein R³ is aryl, substituted aryl or substituted hydrocarbyl and at least 60 mole percent of the functional groups --CO--Y--R³ are attached to a tertiary carbon atom of the polymer backbone.

3. The dispersant according to claim 1, wherein the hydrocarbon polymer comprises a member selected from the group consisting of polyalkene homopolymers, polyalkene interpolymers, and mixtures thereof.

4. The dispersant according to claim 1, wherein the hydrocarbon polymer comprises a member selected from the group consisting of alpha-olefin homopolymers, alpha-olefin interpolymers and ethylene alpha-olefin copolymers.

5. The dispersant according to claim 4, wherein the hydrocarbon polymer comprises ethylene alpha-olefin copolymer derived from ethylene and at least one alpha-olefin having the formula H₂ C=CHR⁴ wherein R⁴ is straight chain or branched chain alkyl radical comprising 1 to 18 carbon atoms and wherein at least about 30% of the polymer chains possess terminal vinylidene unsaturation.

6. The dispersant according to claim 5, wherein the ethylene alpha-olefin copolymer has a number average molecular weight of from 500 to 10,000.

7. The dispersant according to claim 5, wherein the ethylene alpha-olefin copolymer comprises ethylene-butene-1 copolymer.

8. The dispersant according to claim 1 wherein the hydrocarbon polymer has a number average molecular weight of from 500 to 20,000.

9. The dispersant according to claim 1, wherein the primary amino group and the 1 to 10 secondary or tertiary amino groups of the polyamine are separated by a hydrocarbylene group.

10. The dispersant according to claim 9, wherein the hydrocarbylene group comprises a propylene (--CH₂ --CH₂ --CH₂ --) group.

11. The dispersant according to claim 1, wherein the polyamine comprises volatile polyamine.

12. The dispersant according to claim 1, wherein the polyamine comprises a polyamine of the formula:

H₂ N(--R⁵ --NH)_z --(R⁶ --A)_y --R₇ wherein R⁵ and R⁶ are hydrocarbyl groups of 1 to 6 carbons;

R⁷ is a hydrocarbyl group of 1 to 40 carbons or a heterocyclic structure containing at least one of N or S;

A is 0 or S;

z is 1 to 10; and

y is 0 or 1.

13. The dispersant according to claim 1, wherein the dispersant is post-treated with a boron compound to obtain a borated dispersant.

14. A lubricating oil composition comprising a base oil and the dispersant according to claim 1.

15. The dispersant according to claim 1, wherein R³ is H or hydrocarbyl, and --Y--R³ has a pKa<

12.

16. An oleaginous composition in the form of a lubricating oil or lubricating oil additive package comprising the dispersant of claim 15 and a base oil.

17. The dispersant according to claim 15 wherein the primary amino group and the 1-10 secondary or tertiary amino groups of the polyamine are separated by a propylene (--CH₂ --CH₂ --CH₂ --)group.

18. The dispersant according to claim 15 wherein said polyamine comprises volatile polyamine.

19. The dispersant according to claim 15 wherein said polyamine comprises a polyamine of the formula:

H₂ N(R₅ --NH)_z --(--R₆ --A)_y --R⁷ wherein R⁵ and R⁶ are hydrocarbyl groups of 1 to 6 carbons;

R⁷ is a hydrocarbyl group of 1-40 carbons or a heterocyclic structure containing at least one of N or S;

A is O or S;

z=1-10; and

y=0or 1.

20. The dispersant according to claim 15 wherein said polyamine comprises a polyamine prepared by stepwise reacting an alcohol, a monoamine or a polyamine with acrylonitrile and then hydrogenating the product thereof.

21. A fuel composition comprising a dispersant of claim 15.