Oil soluble dispersant additives useful in oleaginous compositions

• US 5,026,495 A
• Filed: 12/29/1988
• Issued: 06/25/1991
• Est. Priority Date: 11/19/1987
• Status: Expired due to Fees

• Current Assignee: Exxon Chemical Patents Inc. (Exxon Mobil Corporation)
• Original Assignee: Exxon Chemical Patents Inc. (Exxon Mobil Corporation)
• Inventors: Emert, Jacob, Gutierrez, Antonio, Lundberg, Robert D.
• Primary Examiner(s): Howard, Jacqueline V.
• Assistant Examiner(s): Muzzolillo, M.
• Application Number:
  US07/291,573
• Time in Patent Office: 908 Days
• Field of Search: 252/47.5, 252/51.5 R, 252/51.5 A
• US Class Current: 508/225
• 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 149/12 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 159/16 obtained by Mannich reactions
• CPC Class Codes: C10M 2207/042 Epoxides
• CPC Class Codes: C10M 2207/123 polycarboxylic
• CPC Class Codes: C10M 2207/125 having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
• CPC Class Codes: C10M 2207/129 having hydrocarbon chains of thirty or more carbon atoms
• CPC Class Codes: C10M 2207/16 Naphthenic acids
• CPC Class Codes: C10M 2207/22 Acids obtained from polymerised unsaturated acids
• CPC Class Codes: C10M 2207/24 Epoxidised acids; Ester derivatives thereof
• 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 2207/34 Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
• 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 2209/084 Acrylate; Methacrylate
• CPC Class Codes: C10M 2209/086 polycarboxylic, e.g. maleic acid
• CPC Class Codes: C10M 2209/10 Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• 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 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 2215/086 : Imides
• 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 2217/042 : 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 2219/022 : of hydrocarbons, e.g. olefines polyolefins C10M2221/041
• CPC Class Codes: C10M 2219/046 : Overbasedsulfonic acid salts
• CPC Class Codes: C10M 2219/068 : Thiocarbamate metal salts
• CPC Class Codes: C10M 2219/084 : containing hydroxy groups; Derivatives thereof
• 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 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 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 2227/061 : 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 2010/12 : Groups 6 or 16
• CPC Class Codes: C10N 2070/02 : Concentrating of additives

Abstract

An oil soluble dispersant comprising the reaction products of:

(1) oil soluble salts, amides, imides, oxazolines, esters, or mixtures thereof of long chain hydrocarbyl substituted mono- and dicarboxylic acids or their anhydrides; (ii) long chain hydrocarbon having a polyamine attached directly thereto; (iii) Mannich condensation product formed by condensing a long chain hydrocarbyl substituted hydroxy aromatic compound with an aldehyde and a polyalkylene polyamine; and (iv) Mannich condensation product formed by reacting long chain hydrocarbyl substituted mono or dicarboxylic acids or their anhydrides with an aminophenol, which may be optionally hydrocarbyl substituted, to form a long chain hydrocarbyl substituted amide or imide-containing phenol intermediate adduct, and condensing said long chain hydrocarbyl substituted amide or imide-containing phenol adduct with aldehyde and polyamine; said adduct containing at least one reactive group selected from reactive amino groups and reactive hydroxyl groups; and

(2) at least one polyepoxide.

Claims

1. An oil soluble composition dispersant useful as a dispersant additive for lubricating composition comprising the reaction products of:

(1) at least one nitrogen containing adduct selected from the group consisting of (i) Mannich condensation product formed by condensing a long chain hydrocarbyl substituted hydroxy aromatic compound with aldehyde and a polyalkylene polyamine; and

(ii) Mannich condensation product formed by reacting long chain hydrocarbyl substituted mono or dicarboxylic acid or its anhydride with amine containing hydroxy aromatic compound, which may be optionally hydrocarbyl substituted, to form long chain hydrocarbyl substituted amide or imide-containing hydroxy aromatic compound intermediate adduct, and condensing said long chain hydrocarbyl substituted amide or imide-containing hydroxy aromatic compound adduct with aldehyde and polyamine;

said adduct containing at least one reactive group selected from reactive amino groups and reactive hydroxyl groups; and

(2) at least one polyepoxide.

2. The composition according to claim 1 wherein said long chain hydrocarbyl in (ii) is a polymer of a C₂ C₁₈ monoolefin, said polymer having a number average molecular weight of from about 500 to about 6,000.

3. The composition according to claim 1 wherein said polyepoxide contains at least two rings joined by hydrocarbon moieties, substituted hydrocarbon moieties, hydrocarbon moieties containing at least one hetero atom or groups, or substituted hydrocarbon moieties containing at least one hetero atom or group.

4. The composition according to claim 3 wherein said hydrocarbon moieties are selected from alkylene, cycloalkylene, alkenylene, arylene, alkarylene, and alkarylene radicals.

5. The composition according to claim 3 wherein the substituent groups present on the hydrocarbon moieties and the hetero atoms or groups present in the hydrocarbon chain are substantially inert or unreactive at ambient conditions with the oxirane rings of the polyepoxide.

6. The composition according to claim 3 wherein said polyepoxide contains at least two oxirane rings wherein one oxirane ring carbon atom is bonded to two hydrogen atoms.

7. The composition according to claim 6 wherein the second oxirane ring carbon atoms is bonded to a hydrogen atom.

8. The composition according to claim 1 wherein (1) is a nitrogen containing adduct of group (i).

9. The composition according to claim 8 wherein (i) is Mannich condensation product formed by condensing long chain hydrocarbyl substituted phenol aldehyde and polyamine.

10. The composition according to claim 1 wherein (1) is a nitrogen containing adduct of group (ii).

11. The composition according to claim 10 wherein (ii) is Mannich condensation product formed by reacting long chain hydrocarbyl substituted mono or dicarboxylic acid or its anhydride with aminophenol, which may be optionally hydrocarbyl substituted, to form long chain hydrocarbyl substituted amide or imide-containing phenol intermediate adduct, and condensing said long chain hydrocarbyl substituted amide or imide-containing intermediate adduct with aldehyde and polyamine.

12. The composition according to claim 11 wherein said long chain hydrocarbyl is a polymer of at least one C₂ to C₁₈ alpha-olefin, said polymer having a number average molecular weight of from about 500 to about 6,000.

13. A lubricating composition comprising:

(A) major amount of a lubricating oil; and

(B) a minor amount of an oil soluble dispersant which is effective to impart enhanced dispersancy comprising the reaction product of

(1) at least one nitrogen containing adduct selected from the group consisting of (i) Mannich condensation product formed by condensing a long chain hydrocarbyl substituted hydroxy aromatic compound with aldehyde and polyamine; and

(ii) Mannich condensation product formed by reacting long chain hydrocarbyl substituted mono or dicarboxylic acid or its anhydride with amine substituted hydroxy aromatic compound, which may be optionally hydrocarbyl substituted, to form long chain hydrocarbyl substituted amide or imide-containing hydroxy aromatic intermediate adduct, and condensing said long chain hydrocarbyl substituted amide or imide-containing hydroxy aromatic adduct with aldehyde and polyamine;

said adduct containing at least one reactive group selected from reactive amino groups and reactive hydroxyl groups, and

(2) at least one polyepoxide.

14. The composition according to claim 13 wherein said long chain hydrocarbyl in (B) (1) (i) and (B) (1) (ii) is a polymer of at least one C₂ to C₁₈ alpha-olefin, said polymer having a number average molecular weight of about 500 to about 6,000.

15. The composition according to claim 13 wherein said polyepoxide contains at least two oxirane rings joined by hydrocarbon moieties, substituted hydrocarbon moieties, hydrocarbon moieties containing at least one hetero atom or group, or substituted hydrocarbon moieties containing at least one hetero atom or group.

16. The composition according to claim 15 wherein said hydrocarbon moieties are selected from alkylene, alkenylene, cycloalkylene, arylene, aralkylene and alkarylene moieties.

17. The composition according to claim 15 wherein said polyepoxide contains at least two oxirane rings wherein one oxirane ring carbon atom is bonded to two hydrogens.

18. The composition according to claim 17 wherein the second oxirane ring carbon atoms is bonded to a hydrogen atom.

19. The composition according to claim 13 which is an additive concentrate comprising about 5 to 70 wt. % of lubricating oil (A) and 20 to 95 wt. % of (B).

20. The composition according to claim 13 wherein (B) (1) is a nitrogen containing adduct of group (i).

21. The composition according to claim 20 wherein (B) (1) (i) is Mannich condensation product formed by condensing long chain hydrocarbyl substituted phenol with aldehyde and polyamine.

22. The composition according to claim 13 wherein (B) (1) is a nitrogen containing adduct of group (ii).

23. The composition according to claim 22 wherein (B) (1) is Mannich condensation product formed by reacting long chain hydrocarbyl substituted mono or dicarboxylic acid or its anhydride with aminophenol, which may be optionally hydrocarbyl substituted, to form long chain hydrocarbyl substituted amide or imide-containing phenol intermediate adduct, and condensing said long chain hydrocarbyl substituted amide or imide-containing intermediate adduct with aldehyde and polyamine.

24. The composition according to claim 23 wherein said long chain hydrocarbyl is a polymer of at least one C₂ to C₁₈ alpha-olefin, said polymer having a number average molecular weight of from about 500 to about 6,000.