Fuel additives derived from amido-amines

• US 5,238,466 A
• Filed: 07/15/1991
• Issued: 08/24/1993
• Est. Priority Date: 10/07/1986
• Status: Expired due to Fees

• Current Assignee: Exxon Chemical Patents Inc. (Exxon Mobil Corporation)
• Original Assignee: Exxon Chemical Patents Inc. (Exxon Mobil Corporation)
• Inventors: Gutierrez, Antonio, Lundberg, Robert D.
• Primary Examiner(s): Howard, Jacqueline V.
• Application Number:
  US07/730,336
• Time in Patent Office: 771 Days
• Field of Search: 44/331, 260/404.8, 260/401, 260/399, 252/47, 252/51.5 A
• US Class Current: 44/331
• CPC Class Codes: C08F 110/10 Isobutene
• CPC Class Codes: C08F 8/20 Halogenation
• CPC Class Codes: C08F 8/32 by reaction with amines
• CPC Class Codes: C08G 63/912 derived from hydroxycarboxylic acids
• CPC Class Codes: C10L 1/1817 Compounds of uncertain formula; reaction products where mixtures of compounds are obtained
• CPC Class Codes: C10L 1/221 compounds of uncertain formula; reaction products where mixtures of compounds are obtained
• 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: C10M 129/95 Esters
• CPC Class Codes: C10M 133/52 having a carbon chain of 30 or more atoms
• CPC Class Codes: C10M 149/18 Polyamides
• CPC Class Codes: C10M 149/22 Polyamines
• CPC Class Codes: C10M 151/04 Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C10M 159/12 Reaction products
• 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 2205/026 Butene
• CPC Class Codes: C10M 2205/06 containing conjugated dienes
• CPC Class Codes: C10M 2207/027 Neutral salts thereof
• CPC Class Codes: C10M 2207/028 Overbased salts thereof
• CPC Class Codes: C10M 2207/044 Cyclic ethers having four or more ring atoms, e.g. furans, dioxolanes
• CPC Class Codes: C10M 2207/10 Carboxylix acids; Neutral salts thereof
• CPC Class Codes: C10M 2207/129 : having hydrocarbon chains of thirty or more carbon atoms
• CPC Class Codes: C10M 2207/144 : containing hydroxy groups
• CPC Class Codes: C10M 2207/146 : having carboxyl groups bound to carbon atoms of six-membeered aromatic rings having a hydrocarbon substituent of thirty or more carbon atoms
• CPC Class Codes: C10M 2207/16 : Naphthenic acids
• CPC Class Codes: C10M 2207/262 : derived from hydroxy substituted aromatic acids, e.g. salicylates
• CPC Class Codes: C10M 2207/289 : containing free hydroxy groups
• CPC Class Codes: C10M 2209/084 : Acrylate; Methacrylate
• CPC Class Codes: C10M 2209/086 : polycarboxylic, e.g. maleic acid
• CPC Class Codes: C10M 2209/101 : Condensation polymers of aldehydes or ketones and phenols, e.g. Also polyoxyalkylene ether derivatives thereof
• CPC Class Codes: C10M 2209/104 : of alkylene oxides containing two carbon atoms only
• CPC Class Codes: C10M 2209/107 : of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
• CPC Class Codes: C10M 2215/02 : Amines, e.g. polyalkylene polyamines; Quaternary amines
• 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 2215/064 : Di- and triaryl amines
• CPC Class Codes: C10M 2215/065 : Phenyl-Naphthyl amines
• CPC Class Codes: C10M 2215/08 : Amides
• CPC Class Codes: C10M 2215/082 : containing hydroxyl groups; Alkoxylated derivatives
• CPC Class Codes: C10M 2215/086 : Imides
• CPC Class Codes: C10M 2215/12 : Partial amides of polycarboxylic acids
• CPC Class Codes: C10M 2215/122 : Phtalamic acid
• 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 2215/225 : the rings containing both nitrogen and oxygen
• CPC Class Codes: C10M 2215/226 : Morpholines
• CPC Class Codes: C10M 2215/24 : having hydrocarbon substituents containing thirty or more carbon atoms , e.g. nitrogen derivatives of substituted succinic acid
• 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 2217/028 : containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
• 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 2219/044 : Sulfonic acids, Derivatives thereof, e.g. neutral salts
• CPC Class Codes: C10M 2219/046 : Overbasedsulfonic acid salts
• CPC Class Codes: C10M 2219/06 : Thio-acids; Thiocyanates; Derivatives thereof
• CPC Class Codes: C10M 2219/066 : Thiocarbamic type compounds
• CPC Class Codes: C10M 2219/085 : containing carboxyl groups; Derivatives thereof
• CPC Class Codes: C10M 2219/087 : containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
• CPC Class Codes: C10M 2219/088 : Neutral salts
• CPC Class Codes: C10M 2219/089 : Overbased salts
• CPC Class Codes: C10M 2219/10 : Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
• CPC Class Codes: C10M 2219/102 : containing sulfur and carbon only in the ring
• CPC Class Codes: C10M 2219/104 : containing sulfur and carbon with nitrogen or oxygen in the ring
• CPC Class Codes: C10M 2219/106 : Thiadiazoles
• CPC Class Codes: C10M 2221/00 : Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
• CPC Class Codes: C10M 2221/02 : Macromolecular compounds obtained by reactions of monomers involving only carbon-to-carbon unsaturated bonds
• CPC Class Codes: C10M 2223/04 : Phosphate esters
• CPC Class Codes: C10M 2223/042 : Metal salts thereof
• CPC Class Codes: C10M 2223/045 : Metal containing thio derivatives
• CPC Class Codes: C10M 2223/12 : obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
• CPC Class Codes: C10M 2225/04 : obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
• CPC Class Codes: C10M 2225/041 : Hydrocarbon polymers
• 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
• CPC Class Codes: C10M 2227/09 : Complexes with metals
• CPC Class Codes: C10M 2229/041 : containing aliphatic substituents
• CPC Class Codes: C10N 2010/02 : Groups 1 or 11
• CPC Class Codes: C10N 2010/04 : Groups 2 or 12
• CPC Class Codes: C10N 2010/12 : Groups 6 or 16
• 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 2040/06 : Instruments or other precision apparatus, e.g. damping fluids
• CPC Class Codes: C10N 2040/252 : Diesel engines
• CPC Class Codes: C10N 2040/253 : Small diesel engines
• CPC Class Codes: C10N 2040/26 : Two-strokes or two-cycle engines
• CPC Class Codes: C10N 2070/02 : Concentrating of additives
• CPC Class Codes: F02B 1/04 : with fuel-air mixture admission into cylinder

Abstract

The present invention is directed to a fuel additive comprising at least one adduct of (A) a polyolefin of 300 to 10,000 number average molecular weight substituted with at least 0.3 (e.g., from about 1 to 4) mono- or dicarboxylic acid producing moieties (preferably acid or anhydride moieties) per polyolefin molecule, (B) an amido-amine or thioamido-amine characterized by being a reaction product of at least a polyamine and an alpha, beta-unsaturated compound of the formula: ##STR1## wherein X is sulfur or oxygen, Y is --OR⁴, --SR⁴, or --NR⁴ (R⁵) , and R¹, R², R³, R⁴ and R⁵ are the same or different and are hydrogen or substituted or unsubstituted hydrocarbyl.

Claims

1. A process for producing a dispersant useful as an oil additive which comprises:

(a) providing a long chain hydrocarbyl substituted mono- or dicarboxylic acid producing material formed by reacting an olefin polymer of C₂ to C₁₀ monoolefin having a number average molecular weight of about 300 to 10,000 and at least one of a C₄ to C₁₀ monounsaturated dicarboxylic acid material and a C₃ to C₁₀ monounsaturated monocarboxylic acid material, said acid producing material having an average of at least about 0.3 dicarboxylic acid producing moieties, per molecule of said olefin polymer present in the reaction mixture used to form said acid producing material;

(b) providing an amido-amine compound having at least one primary amino group prepared by reacting at least one polyamine with at least one alpha, beta-unsaturated compound of the formula;

##STR24## wherein X is sulfur or oxygen, Y is --OR⁴,--SR⁴, or --NR⁴ (R⁵) , and R¹, R², R³, R⁴ and R⁵ are the same or different and are hydrogen or substituted or unsubstituted hydrocarbyl; and

(c) contacting the said acid producing material with said amido-amine compound under conditions sufficient to effect reaction of at least a portion of the primary amino groups on said amido-amine compound with at least a portion of the acid-producing groups in said acid producing material, to form said dispersant.

2. The process according to claim 1 wherein said polyamine comprises amines containing from 2 to 60 carbon atoms and from 2 to 12 nitrogen atoms per molecule.

3. The process according to claim 2, wherein said polyamine comprises a polyalkylenepolyamine wherein each said alkylene group contains from 2 to 40 carbons and said polyalkylenepolyamine contains from 5 to about 9 nitrogen atoms per molecule.

4. The process according to claim 1, wherein said hydrocarbyl substituted acid producing material comprises a hydrocarbyl substituted C₄ to C₁₀ monounsaturated dicarboxylic acid producing material which comprises polyisobutylene of about 900 to 5000 number average molecular weight substituted with succinic anhydride moieties, said amine comprises polyalkylenepolyamine wherein each said alkylene group contains from 2 to 6 carbons and said polyalkyenepolyamine contains from 5 to 9 nitrogen atoms per molecule, and an acrylate-type compound comprising at least one member selected from the group consisting of methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, methyl methacrylate, ethyl methacylate, propyl methacrylate, and butyl methacrylate.

5. The process according to claims 1 or 4, wherein said polyamine comprises polyethylenepolyamine.

6. The process according to claims 1 or 4, wherein said dispersant is borated to provide from about 0.05 to 2.0 weight percent boron in said borated dispersant.

7. The process according to claim 1, wherein the ratio of acid producing moieties per molecule of olefin polymer in said dispersant is from about 0.9 to 1.3

8. The process of claim 7, wherein said number average molecular weight of said fist olefin polymer is from about 1300 to 4,000.

9. The process of claim 8, wherein said monounsaturated acid material comprises maleic anhydride.