Lactone-modified, mannich base dispersant additives useful in oleaginous compositions

• US 4,913,830 A
• Filed: 01/09/1989
• Issued: 04/03/1990
• Est. Priority Date: 07/24/1987
• Status: Expired due to Fees

• Current Assignee: Exxon Chemical Patents Inc. (Exxon Mobil Corporation)
• Original Assignee: Exxon Chemical Patents Inc. (Exxon Mobil Corporation)
• Inventors: Gutierrez, Antonio, Lundberg, Robert D.
• Primary Examiner(s): Dixon, Jr., William R.
• Assistant Examiner(s): Johnson, Jerry D.
• Application Number:
  US07/294,459
• Time in Patent Office: 449 Days
• Field of Search: 549/213, 564/9, 560/189, 252/49.6
• US Class Current: 508/194
• CPC Class Codes: C08G 63/6852 derived from hydroxy carboxylic acids
• CPC Class Codes: C10L 1/221 compounds of uncertain formula; reaction products where mixtures of compounds are obtained
• CPC Class Codes: C10M 159/16 obtained by Mannich reactions
• CPC Class Codes: C10M 2203/06 Well-defined aromatic compounds
• 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 2207/027 Neutral salts thereof
• CPC Class Codes: C10M 2207/028 Overbased salts thereof
• 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 2209/084 Acrylate; Methacrylate
• CPC Class Codes: C10M 2209/086 polycarboxylic, e.g. maleic acid
• CPC Class Codes: C10M 2215/04 having amino groups bound to acyclic or cycloaliphatic carbon atoms
• 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 2215/26 Amines
• CPC Class Codes: C10M 2215/28 Amides; Imides
• 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 2219/022 : of hydrocarbons, e.g. olefines
• 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 2219/084 : containing hydroxy 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 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 2227/061 : Esters derived from boron
• CPC Class Codes: C10M 2227/09 : Complexes with metals
• CPC Class Codes: C10M 2229/041 : containing aliphatic substituents
• 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 2040/25 : Internal-combustion engines
• CPC Class Codes: C10N 2040/251 : Alcohol-fuelled 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 2040/28 : Rotary engines
• CPC Class Codes: C10N 2070/02 : Concentrating of additives

Abstract

Poly (C₅ -C₉ lactone) modified Mannich base adducts are made by reacting a C₅ -C₉ lactone, an amine, an aldehyde, and a hydrocarbyl substituted, hydroxy aromatic compound, e.g. a polyisobutenyl phenol which, in turn, preferably is made by reacting a polymer of a C₂ to C₁₀ monoolefin, preferably polyisobutylene, having a molecular weight of about 700 to 10,000 with a hydroxy aromatic compound. The resulting adducts are useful per se as oil soluble dispersant additives. They are also useful in fuel and lubricating oil compositions, as well as in concentrates and additive packages.

Claims

1. A post-treated poly(C₅ -C₉ lactone) modified Mannich base useful as an oil additive and formed by reacting a C₅ -C₉ lactone, an amine, an aldehyde, and a hydrocarbyl hydroxy aromatic compound, said hydrocarbyl substituted hydroxy aromatic compound being formed by reacting an olefin polymer of a C₂ -C₁₀ monoolefin having a number average molecular weight of about 700 to about 10,000 and a hydroxy aromatic material, and said poly (C₅ -C₉ lactone) modified Mannich base adduct containing the unit ##STR14## wherein m has an average value of from 0.2 to about 100, and z is 4 to 8, and post-treating said adduct with a boron compound.

2. The post-treated poly (C₅ -C₉ lactone) modified Mannich base adduct according to claim 1, wherein said adduct has been prepared by first reacting said hydrocarbyl substituted hydroxy aromatic compound with said amine and said aldehyde to form an intermediate Mannich base adduct having an amino functional group capable of initiating lactone open ring polymerization, and then reacting said lactone with said intermediate Mannich base adduct.

3. The post-treated poly (C₅ -C₉ lactone) modified Mannich base adduct according to claim 1, wherein said adduct has been prepared by first reacting said amine with said lactone to form a poly(C₅ -C₉ lactone) intermediate adduct, and thereafter mixing said intermediate poly(C₅ -C₉ lactone) adduct with said aldehyde and said hydrocarbyl substituted hydroxy aromatic compound, and subjecting the admixture to a Mannich base reaction.

4. The post-treated poly (C₅ -C₉ lactone) modified Mannich base adduct according to claim 1, wherein said adduct has been prepared by first reacting said lactone with said hydrocarbyl substituted hydroxy aromatic compound to form a poly(C₅ -C₉ lactone) intermediate adduct, and thereafter reacting with said poly(C₅ -C₉ lactone) intermediate adduct a mixture of said aldehyde and said amine.

5. The post-treated poly (C₅ -C₉ lactone) modified Mannich base adduct according to claim 1, wherein said adduct has been prepared by first reacting said amine with said aldehyde and said C₅ -C₉ lactone to form a Mannich base intermediate, and then admixing and reacting said hydrocarbyl substituted hydroxy aromatic compound with said Mannich base intermediate.

6. The post-treated poly (C₅ -C₉ lactone) modified Mannich base adduct material according to claim 2, wherein said C₅ -C₉ lactone is E-caprolactone.

7. The post-treated poly (C₅ -C₉ lactone) modified Mannich base adduct material according to claim 3, wherein said C₅ -C₉ lactone is E-caprolactone.

8. The post-treated poly (C₅ -C₉ lactone) modified Mannich base adduct material according to claim 4, wherein said C₅ -C₉ lactone is E-caprolactone.

9. The post-treated poly (C₅ -C₉ lactone) modified Mannich base adduct material according to claim 5, wherein said C₅ -C₉ lactone is E-caprolactone.

10. The post-treated poly (C₅ -C₉ lactone) modified Mannich base adduct material according to claim 1, wherein said C₅ -C₉ lactone is E-caprolactone.

11. The post-treated adduct material according to claim 2, wherein said hydrocarbyl substituted hydroxy aromatic material is a member selected from the group of materials having the formula

12. The post-treated adduct material according to claim 3, wherein said hydrocarbyl substituted hydroxy aromatic material is a member selected from the group of materials having the formula

13. The post-treated adduct material according to claim 4, wherein said hydrocarbyl substituted hydroxy aromatic material is a member selected from the group of materials having the formula

14. The post-treated adduct material according to claim 5, wherein said hydrocarbyl substituted hydroxy aromatic material is a member selected from the group of materials having the formula

15. The post-treated adduct material according to claim 11, wherein said hydrocarbyl-substituted hydroxy aromatic compound is a polyolefin phenol.

16. The post-treated adduct material according to claim 12, wherein said hydrocarbyl-substituted hydroxy aromatic compound is a polyolefin phenol.

17. The post-treated adduct material according to claim 13, wherein said hydrocarbyl-substituted hydroxy aromatic compound is a polyolefin phenol.

18. The post-treated adduct material according to claim 14, wherein said hydrocarbyl-substituted hydroxy aromatic compound is a polyolefin phenol.

19. The post-treated adduct material according to claim 15, wherein said olefin polymer is polyisobutylene.

20. The post-treated adduct material according to claim 16, wherein said olefin polymer is polyisobutylene.

21. The post-treated adduct material according to claim 17, wherein said olefin polymer is polyisobutylene.

22. The post-treated adduct material according to claim 18, wherein said olefin polymer is polyisobutylene.

23. The post-treated adduct material according to claim 2, wherein said amine is selected from the group consisting of polyamines of about 2 to 60 total carbon atoms and about 2 to 12 nitrogen atoms in the molecule.

24. The post-treated adduct material according to claim 3, wherein said amine is selected from the group consisting of polyamines of about 2 to 60 total carbon atoms and about 2 to 12 nitrogen atoms in the molecule.

25. The post-treated adduct material according to claim 4, wherein said amine is selected from the group consisting of polyamines of about 2 to 60 total carbon atoms and about 2 to 12 nitrogen atoms in the molecule.

26. The post-treated adduct material according to claim 5, wherein said amine is selected from the group consisting of polyamines of about 2 to 60 total carbon atoms and about 2 to 12 nitrogen atoms in the molecule.

27. The post-treated adduct material according to claim 23, wherein said amine is an aliphatic saturated amine having the formula ##STR19## wherein R and R'"'"' independently are selected from the group consisting of hydrogen, C₁ to C₂₅ straight or branched chain alkyl radicals, C₁ to C₁₂ alkoxy C₂ to C₆ alkylene radicals, and C₁ to C₁₂ alkylamino C₂ to C₆ alkylene radicals;

each s is the same or a different number of from 2 to 6; and

t is a number of from 0 to 10, with the provision that when t=0, at least one of R or R'"'"' must be H such that there are at least two of either primary or secondary amino groups.

28. The post-treated adduct material according to claim 24, wherein said amine is an aliphatic saturated amine having the formula ##STR20## wherein R and R'"'"' independently are selected from the group consisting of hydrogen, C₁ to C₂₅ straight or branched chain alkyl radicals, C₁ to C₁₂ alkoxy C₂ to C₆ alkylene radicals, and C₁ to C₁₂ alkylamino C₂ to C₆ alkylene radicals;

each s is the same or a different number of from 2 to 6; and

t is a number of from 0 to 10, with the provision that when t=0, at least one of R or R'"'"' must be H such that there are at least two of either primary or secondary amino groups.

29. The post-treated adduct material according to claim 25, wherein said amine is an aliphatic saturated amine having the formula ##STR21## wherein R and R'"'"' independently are selected from the group consisting of hydrogen, C₁ to C₂₅ straight or branched chain alkyl radicals, C₁ to C₁₂ alkoxy C₂ to C₆ alkylene radicals, and C₁ to C₁₂ alkylamino C₂ to C₆ alkylene radicals;

each s is the same or a different number of from 2 to 6; and

t is a number of from 0 to 10, with the provision that when t=0, at least one of R or R'"'"' must be H such that there are at least two of either primary or secondary amino groups.

30. The post-treated adduct material according to claim 26, wherein said amine is an aliphatic saturated amine having the formula ##STR22## wherein R and R'"'"' independently are selected from the group consisting of hydrogen, C₁ to C₂₅ straight or branched chain alkyl radicals, C₁ to C₁₂ alkoxy C₂ to C₆ alkylene radicals, and C₁ to C₁₂ alkylamino C₂ to C₆ alkylene radicals;

each s is the same or a different number of from 2 to 6; and

t is a number of from 0 to 10, with the provision that when t=0, at least one of R or R'"'"' must be H such that there are at least two of either primary or secondary amino groups.

31. The post-treated adduct material of claim 27, wherein said amine is selected from the group consisting of 1, 2-diaminoethane;

1, 3-diaminopropane;

1, 4-diaminobutane;

1, 6-diaminohexane;

diethylene triamine;

triethylene tetramine;

tetraethylene pentamine;

1, 2-propylene diamine;

di-(1, 2-propylene)triamine;

di-(1, 3-propylene) triamine;

N, N-dimethyl-1, 3-diaminopropane;

N, N-di-(2-aminoethyl) ethylene diamine; and

N-dodecyl-1, 3-propane diamine.

32. The post-treated adduct material of claim 28, wherein said amine is selected from the group consisting of 1, 2-diaminoethane;

1, 3-diaminopropane;

1, 4-diaminobutane;

1, 6-diaminohexane;

diethylene triamine;

triethylene tetramine;

tetraethylene pentamine;

1, 2-propylene diamine;

di-(1, 2-propylene)triamine;

di-(1, 3-propylene) triamine;

N, N-dimethyl-1, 3-diaminopropane;

N, N-di-(2-aminoethyl) ethylene diamine; and

N-dodecyl-1, 3-propane diamine.

33. The post-treated adduct material of claim 29, wherein said amine is selected from the group consisting of 1, 2-diaminoethane;

1, 3-diaminopropane;

1, 4-diaminobutane;

1, 6-diaminohexane;

diethylene triamine;

triethylene tetramine;

tetraethylene pentamine;

1, 2-propylene diamine;

di-(1, 2-propylene)triamine;

di-(1, 3-propylene) triamine;

N, N-diemthyl-1, 3-diaminopropane;

N, N-di-(2-aminoethyl) ethylene diamine; and

N-dodecyl-1, 3-propane diamine.

34. The post-treated adduct material of claim 30, wherein said amine is selected from the group consisting of 1, 2-diaminoethane;

1, 3-diaminopropane;

1, 4-diaminobutane;

1, 6-diaminohexane;

diethylene triamine;

triethylene tetramine;

tetraethylene pentamine;

1, 2-propylene diamine;

di-(1, 2-propylene)triamine;

di-(1, 3-propylene) triamine;

N, N-dimethyl-1, 3-diaminopropane;

N, N-di-(2-aminoethyl) ethylene diamine; and

N-dodecyl-1, 3-propane diamine.

35. The post-treated adduct material according to claim 23, wherein said amine is selected from the group consisting of alicyclic diamines, imidazolines, morpholines, and N-aminoalkyl piperazines of the general formula:

##STR23## wherein G is independently selected from the group consisting of hydrogen and omega-(non-tertiary)aminoalkylene radicals of from 1 to 3 carbon atoms, and p is a number of from 1 to 4.

36. The post-treated adduct material according to claim 24, wherein said amine is selected from the group consisting of alicyclic diamines, imidazolines, morpholines, and N-aminoalkyl piperazines of the general formula:

##STR24## wherein G is independently selected from the group consisting of hydrogen and omega-(non-tertiary)aminoalkylene radicals of from 1 to 3 carbon atoms, and p is a number of from 1 to 4.

37. The post-treated adduct material according to claim 25, wherein said amine is selected from the group consisting of alicyclic diamines, imidazolines, morpholines, and N-aminoalkyl piperazines of the general formula:

##STR25## wherein G is independently selected from the group consisting of hydrogen and omega-(non-tertiary)aminoalkylene radicals of from 1 to 3 carbon atoms, and p is a number of from 1 to 4.

38. The post-treated adduct material according to claim 26, wherein said amine is selected from the group consisting of alicyclic diamines, imidazolines, morpholines, and N-aminoalkyl piperazines of the general formula:

##STR26## wherein G is independently selected from the group consisting of hydrogen and omega-(non-tertiary)aminoalkylene radicals of from 1 to 3 carbon atoms, and p is a number of from 1 to 4.

39. The post-treated adduct material according to claim 23, wherein said amine is a mixture of poly (ethyleneamines) averaging about 5 to about 7 nitrogen atoms per molecule.

40. The post-treated adduct material according to claim 24, wherein said amine is a mixture of poly (ethyleneamines) averaging about 5 to about 7 nitrogen atoms per molecule.

41. The post-treated adduct material according to claim 25, wherein said amine is a mixture of poly (ethyleneamines) averaging about 5 to about 7 nitrogen atoms per molecule.

42. The post-treated adduct material according to claim 26, wherein said amine is a mixture of poly (ethyleneamines) averaging about 5 to about 7 nitrogen atoms per molecule.

43. The post-treated adduct material of claim 19, wherein said C₅ -C₉ lactone is E-caprolactone.

44. The post-treated adduct material of claim 20, wherein said C₅ -C₉ lactone is E-caprolactone.

45. The post-treated adduct material of claim 21, wherein said C₅ -C₉ lactone is E-caprolactone.

46. The post-treated adduct material of claim 22, wherein said C₅ -C₉ lactone is E-caprolactone.

47. The post-treated adduct material of claim 1, wherein said post-treatment is conducted with a boron compound selected from the group consisting of borates of iron, cobalt, nickel, copper, chromium, manganese, molybdenum, tungsten, ruthenium, palladium, platinum, cadmimum, lead, silver, mercury and antimony.

48. The post-treated adduct material of claim 1, wherein the post-treatment is conducted with a boron compound selected from the group consisting of a boron oxide, boron oxide hydrate, boron halide, boron ester and boron ester.

49. The post-treated adduct material according to claim 1, wherein the average value of m is 1 to about 20.

50. The post-treated adduct material according to claim 6, wherein the average value of m is 1 to about 20.

51. The post-treated adduct material according to claim 43, wherein the average value of m is 1 to about 20.

60. A lubricating oil composition comprising lubricating oil and about 0.01 to 15 wt. % of the post-treated poly (C₅ -C₉) lactone modified Mannich base adduct material of claim 1.

61. A lubricating oil comprising a major amount of lubricating oil and about 0.1 to 10 wt. % of the post-treated poly (C₅ -C₉) lactone modified Mannich base adduct material of claim 1.

62. A lubricating oil comprising a major amount of lubricating oil and about 0.1 to 10 wt. % of the post-treated poly (C₅ -C₉) lactone modified Mannich base adduct material according to claim 2.

63. A lubricating oil comprising a major amount of lubricating oil and about 0.1 to 10 wt. % of the post-treated poly (C₅ -C₉) lactone modified Mannich base adduct material according to claim 3.

64. A lubricating oil comprising a major amount of lubricating oil and about 0.1 to 10 wt. % of the post-treated poly (C₅ -C₉) lactone modified Mannich base adduct material according to claim 4.

65. A lubricating oil comprising a major amount of lubricating oil and about 0.1 to 10 wt. % of the post-treated poly (C₅ -C₉) lactone modified Mannich base adduct material according to claim 5.

66. A lubricating oil comprising a major amount of lubricating oil and about 0.1 to 10 wt. % of the post-treated poly (C₅ -C₉) lactone modified Mannich base adduct material according to claim 51.

67. An oil composition containing 0.01 to 15 wt. %, based on the weight of the total composition, of a borated poly (C₅ -C₉ lactone) modified Mannich base adduct material according to claim 48.

68. A lubricating oil composition containing 0.01 to 15 wt. %, based on the weight of the total composition, of a poly (C₅ -C₉ lactone) modified Mannich base adduct material according to claim 2.

69. A lubricating oil composition containing 0.01 to 15 wt. %, based on the weight of the total composition, of a post-treated poly (C₅ -C₉ lactone) modified Mannich base adduct material according to claim 3.

70. A lubricating oil composition containing 0.01 to 15 wt. %, based on the weight of the total composition, of a post-treated poly (C₅ -C₉ lactone) modified Mannich base adduct material according to claim 4.

71. A lubricating oil composition containing 0.01 to 15 wt. %, based on the weight of the total composition, of a post-treated poly (C₅ -C₉ lactone) modified Mannich base adduct material according to claim 5.

52. An oleaginous composition comprising a fuel lubricating, and a poly (C₅ -C₉ lactone) modified Mannich base adduct material prepared by reacting an amine, a hydrocarbyl substituted hydroxy aromatic compound, an aldehyde, and a C₅ -C₉ lactone, wherein said hydrocarbyl substituted hydroxy aromatic compound has been formed by reacting an olefin polymer of a C₂ -C₁₀ monoolefin of 700 to about 10,000 M_n with a hydroxy aromatic compound, and wherein said poly (C₅ -C₉ lactone) modified Mannich base adduct material contains the unit ##STR27## where m is a number having an average value of from 0.2 to about 100, and z is 4 to 8.

53. An oleaginous composition according to claim 52, wherein said poly(C₅ -C₉ lactone) modified Mannich base adduct material has been prepared by first reacting said hydrocarbyl substituted hydroxy aromatic compound with said amine and said aldehyde to form an intermediate Mannich base adduct having an amino functional group capable of initiating lactone open ring polymerization, and then reacting said lactone with said intermediate adduct.

54. An oleaginous composition according to claim 52, wherein said poly(C₅ -C₉ lactone) modified Mannich base adduct material has been prepared by first reacting said amine with said lactone to form poly(C₅ -C₉ lactone) intermediate adduct, and thereafter mixing said intermediate adduct with said aldehyde and said hydrocarbyl substituted hydroxy aromatic compound, subjecting the admixture to a Mannich base reaction.

55. An oleaginous composition according to claim 52, wherein said poly(C₅ -C₉ lactone) modified Mannich base adduct material has been prepared by first reacting said lactone with said hydrocarbyl substituted hydroxy aromatic compound to form a poly (C₅ -C₉ lactone) intermediate adduct, and thereafter reacting with said poly(C₅ -C₉ lactone) adduct a mixture of said aldehyde and said amine.

56. An oleaginous composition according to claim 52, wherein said poly(C₅ -C₉ lactone) modified Mannich base adduct material has been prepared by first reacting said amine with said aldehyde and said C₅ -C₉ lactone to form a Mannich base intermediate, and then admixing and reacting said hydrocarbyl substituted hydroxy aromatic compound with said Mannich base intermediate.

57. The oleaginous composition according to claim 52, wherein said C₅ -C₉ lactone monomer is E-caprolactone.

58. The oleaginous composition according to claim 52, wherein said poly(C₅ -C₉ lactone) modified Mannich base adduct material has been post-treated with a complex-forming metal or boron compound.

59. The oleaginous composition according to claim 58, wherein the post-treatment is conducted with a boron oxide, boron oxide hydrate, boron halide, boron ester and boron acid.

72. A post-treated oil soluble dispersant useful as an oil additive, comprising the product of a reaction of:

(I) a hydrocarbyl substituted hydroxy aromatic compound of the formula

space="preserve" listing-type="equation">R'"'"'.sup.b -Ar-(OH).sup.d

wherein Ar represents ##STR28## wherein a is 1 or 2, R'"'"' is a long chain hydrocarbon, R" is a hydrocarbon or substituted hydrocarbon radical having from 1 to about 3 carbon atoms or a halogen radical, b is an integer from 1 to 2, c is an integer from 0 to 2, and d is an integer from 1 to 2;

(II) a C₅ -C₉ lactone, wherein there are, on the average, 0.2 to about 100 C₅ -C₉ lactone derived moieties per moiety of said hydrocarbyl substituted hydroxy aromatic compound used in the reaction;

(III) an aldehyde having the formula R"CHO, where R" is hydrogen or an aliphatic hydrocarbon radical having from 1 to 4 carbon atoms; and

(IV) an amine, said product having been post-treated with a boron compound.

73. An post-treated oil soluble dispersant according to claim 72 wherein said dispersant has been prepared by first reacting said amine with said hydrocarbyl substituted aromatic compound and said aldehyde to form an intermediate Mannich base adduct having an amino functional group capable of initiating lactone open ring polymerization, and then reacting said lactone with said intermediate Mannich base adduct.

74. An post-treated oil soluble dispersant according to claim 72, wherein said dispersant has been prepared by first reacting said amine with said C₅ -C₉ lactone to form poly(C₅ -C₉ lactone) intermediate adduct, and thereafter mixing said intermediate poly(C₅ -C₉ lactone) adduct with said aldehyde and said hydrocarbyl-substituted hydroxy aromatic compound, and subjecting the admixture to a Mannich base reaction.

75. An post-treated oil soluble dispersant according to claim 72, wherein said dispersant has been prepared by first reacting said lactone with said hydrocarbyl-substituted hydroxy aromatic compound to form a poly (C₅ -C₉ lactone) intermediate adduct, and thereafter reacting with said poly (C₅ -C₉ lactone) adduct a mixture of said aldehyde and said amine.

76. An post-treated oil soluble dispersant according to claim 72, wherein said dispersant has been prepared by first reacting said amine with said aldehyde and said C₅ -C₉ lactone to form a Mannich base intermediate, and then admixing and reacting said hydrocarbyl substituted hydroxy aromatic compound with said Mannich base intermediate.

77. An post-treated oil soluble dispersant according to claim 72, wherein said C₅ -C₉ lactone is E-caprolactone, and wherein said dispersant contains the unit ##STR29## wherein m is from 1 to about 20.

78. An post-treated oil soluble dispersant according to claim 77, wherein said polyamine is selected from the group consisting of polyamines of about 2 to 60 total carbon atoms and about 2 to 12 nitrogen atoms in the molecule.

79. An post-treated oil soluble dispersant according to claim 78, wherein said polyamine is an aliphatic saturated amine having the general formula ##STR30## wherein R and R'"'"' independently are selected from the group consisting of hydrogen, C₁ to C₂₅ straight or branched chain alkyl radicals, C₁ to C₁₂ alkoxy C₂ to C₆ alkylene radicals, and C₁ to C₁₂ alkylamino C₂ to C₆ alkylene radicals;

each s is the same or a different number of from 2 to 6; and

t is a number of from 0 to 10, with the proviso that when t=0, at least one of R or R'"'"' must be H such that there are at least two of either primary or secondary amino groups.

80. An post-treated oil soluble dispersant according to claim 79, wherein said polyamine is selected from the group consisting of 1,2-diaminoethane;

1,3-diaminopropane;

1,4-diaminobutane;

1,6-diaminohexane;

diethylene triamine;

triethylene tetramine;

tetraethylene pentamine;

1,2-propylene diamine;

di-(1,2-propylene)triamine;

di-(1,3-propylene triamine;

N,N-dimethyl-1,3-diaminopropane;

N,N-di-(2-aminoethyl) ethylene diamine; and

N-dodecyl-1,3-propane diamine.

81. The post-treated oil soluble dispersant of claim 78, wherein said amine is selected from the group consisting alicyclic diamines, imidazoles, morpholines, and N-aminoalkyl piperazines of the general formula:

##STR31##

82. The post-treated oil soluble dispersant according to claim 78, wherein said polyamine is a mixture of poly(ethyleneamines) averaging about 5 to about 7 nitrogen atoms per molecule.

83. The post-treated oil soluble dispersant according to claim 78, wherein said polyamine is a polyoxyalkylene polyamine having the formula:

space="preserve" listing-type="equation">NH.sub.2 -alkylene-(O-alkylene).sub.m -NH.sub.2

where m has a value of about 3 to 70;

or

space="preserve" listing-type="equation">R-[alkylene-(O-alkylene).sub.n -NH.sub.2 ].sub.a

where n has a value of about 1 to 40 with the proviso that the sum of all the n'"'"'s is from about 3 to about 70, R is a substituted saturated hydrocarbon radical of up to ten carbon atoms, wherein the number of substituents on the R group is represented by the value of "a", which is a number from 3 to 6.

84. The post-treated oil soluble dispersant according to claim 72, wherein said post-treatment is conducted with a boron compound selected from the group consisting of borates of iron, cobalt, nickel, copper, chromium, manganese, molybdenum, tungsten, ruthenium, palladium, platinum, cadmium, lead, silver, mercury and antimony.

85. The post-treated oil soluble dispersant according to claim 72, wherein the post-treatment is conducted with a boron compound selected from the group consisting of a boron oxide, boron oxide hydrate, boron halide, boron ester and boron acid.

86. A post-treated oil soluble reaction product useful as an oil additive comprising an oil soluble reaction product of:

(a) polymer consisting essentially of C₂ to C₁₀ monoolefin, said polymer having a number average molecular weight of 700 to 10,000 and being substituted with hydroxy aromatic moieties selected from the group consisting of hydroxy phenyl, substituted hydroxy phenyl, hydroxy naphthyl, and substituted hydroxy naphthyl,

(b) amine containing 2 to 60 carbon atoms and 2 to 12 nitrogen groups,

(c) aldehyde having the formula,

space="preserve" listing-type="equation">RCHO,

where R is hydrogen or an aliphatic hydrocarbon radical having 1 to 4 carbon atoms, and

(d) C₅ -C₉ lactone, wherein there are, on the average, about 0.2 to 100 molar proportions of (d) per molar proportion of said oil soluble reaction product, and wherein said oil soluble reaction product is post-treated with a boron compound.

87. The post-treated oil soluble reaction product of claim 86 wherein (a) is first reacted with (b) and (c) to form a Mannich base intermediate, and wherein (d) is then reacted with said Mannich base intermediate.

88. The post-treated oil soluble reaction product of claim 86 wherein (b) is first reacted with (d) to form a poly(C₅ -C₉ lactone) intermediate, and wherein a mixture of (a) and (c) is then reacted with said poly (C₅ -C₉ lactone) intermediate.

89. The post-treated oil soluble reaction product of claim 86 wherein (a) is reacted with (d) to form a poly (C₅ -C₉ lactone) intermediate, and wherein said poly (C₅ -C₉ lactone) intermediate is then reacted with a mixture of (b) and (c).

90. The post-treated oil soluble reaction product of claim 86 wherein (b) is reacted with (c) and (d) to form a poly(C₅ -C₉ lactone) intermediate, and wherein (a) is then reacted with said poly (C₅ -C₉ lactone) intermediate.

91. The post-treated oil soluble reaction product according to claim 86, wherein (b) is an aliphatic saturated amine having the general formula ##STR32## wherein R and R'"'"' independently are selected from the group consisting of hydrogen, C₁ to C₂₅ straight or branched chain alkyl radicals, C₁ to C₁₂ alkoxy C₂ to C₆ alkylene radicals, and C₁ to C₁₂ alkylamino C₂ to C₆ alkylene radicals;

each s is the same or a different number of from 2 to 6, and t is a number of from 0 to 10, with the provison that when t=0, at least one of R or R'"'"' must be H such that there are at least two of either primary or secondary amino groups.

92. The post-treated oil soluble reaction product according to claim 91, wherein (b) is amine is selected from the group consisting of 1,2-diaminoethane;

1,3-diaminopropane;

1,4-diaminobutane;

1,6-diaminohexane;

diethylene triamine;

triethylene tetramine;

tetraethylene pentamine;

1,2-propylene diamine;

di-(1,2-propylene)triamine;

di-(1,3propylene triamine;

N,N-dimethyl-1,3-diaminopropane;

N,N-di-(2-aminoethyl) ethylene diamine; and

N-dodecyl-1,3-propane diamine.

93. The post-treated oil soluble reaction product according to claim 86, wherein (b) is a mixture of poly(ethyleneamines) averaging about 5 to about 7 nitrogen atoms per molecule.

94. The post-treated oil soluble reaction product according to claim 86, wherein (a) is polyisobutylene of about 700 to 3,000 molecular weight substituted with hydroxy phenyl or substituted hydroxy phenyl moieties.

95. The post-treated oil soluble reaction product according to claim 94, wherein (d) is E-caprolactone and wherein there are about 1 to 20 molar proportions of (d) per molar proportion of said reaction product.

96. The post-treated oil soluble reaction product according to claim 95, wherein (b) is an aliphatic saturated amine having the general formula ##STR33## wherein R and R'"'"' independently are selected from the group consisting of hydrogen, C₁ to C₂₅ straight or branched chain alkyl radicals, C₁ to C₁₂ alkoxy C₂ to C₆ alkylene radicals, and C₁ to C₁₂ alkylamino C₂ to C₆ alkylene radicals;

each s is the same or a different number of from 2 to 6, and t is a number of from 0 to 10, with the provison that when t=0, at least one of R or R'"'"' is H such that there are at least two of either primary or secondary amino groups.

97. The post-treated oil soluble reaction product according to claim 95, wherein (b) is a mixture of poly(ethyleneamines) averaging about 5 to about 7 nitrogen atoms per molecule.

98. The post-treated oil soluble reaction product according to claim 86 wherein said post-treatment is conducted with a boron compound selected from the group consisting of borates of iron, cobalt, nickel, copper, chromium, manganese, molybdenum, tungsten, ruthenium, palladium, platinum, cadmium, lead, silver, mercury and antimony.

99. An oleaginous composition comprising lubricating oil containing the oil soluble reaction product of claim 86.

100. The oleaginous composition according to claim 99, wherein said oleaginous material is lubricating oil.

101. The oleaginous composition of claim 99, wherein said lactone is E-caprolactone and wherein there are, on the average, from about 1 to 20 molar proportions of lactone per molar proportion of said oil soluble reaction product.

102. The oleaginous composition according to claim 99, wherein said amine is an aliphatic saturated amine having the general formula ##STR34## wherein R and R'"'"' independently are selected from the group consisting of hydrogen, C₁ to C₂₅ straight or branched chain alkyl radicals, C₁ to C₁₂ alkoxy C₂ to C₆ alkylene radicals, and C₁ to C₁₂ alkylamino C₂ to C₆ alkylene radicals;

each s is the same or a different number of from 2 to 6, and t is a number of from 0 to 10, with the provison that when t=0, at least one of R and R'"'"' is H such that there are at least two primary or secondary amino groups present in said polyamine.

103. The oleaginous composition according to claim 99, wherein said amine is a mixture of poly(ethyleneamines) averaging about 5 to about 7 nitrogen atoms per molecule.

104. The oleaginous composition according to claim 101, wherein (a) is polyisobutylene of about 700 to 3,000 molecular weight substituted with hydroxy phenyl or substituted hydroxy phenyl moieties.

105. The oleaginous composition according to claim 99, wherein (a) is polyisobutylene of about 700 to 3,000 molecular weight substituted with hydroxy phenyl or substituted hydroxy phenyl moieties.

106. The oleaginous composition according to claim 99, wherein said post-treatment is conducted with a boron compound selected from the group consisting of borates of iron, cobalt, nickel, copper, chromium, manganese, molybdenum, tungsten, ruthenium, palladium, platinum, cadmium, lead, silver, mercury and antimony.

107. A lubricating crankcase motor oil composition for automotive vehicles and trucks comprising a major amount of lubricating oil;

from about 0.01 to 15 wt. % of the post-treated oil soluble reaction product of claim 86; and

an effective amount of a viscosity modifier.

108. The composition according the claim 107, wherein said composition also contains an effective amount of an anti-wear agent.

109. A lubricating crankcase motor oil composition for automotive vehicles and trucks comprising a major amount of lubricating oil;

from about 0.01 to 15 wt. % of the post-treated oil soluble reaction product of claim 87; and

an effective amount of a viscosity modifier.

110. The composition according the claim 109, wherein said composition also contains an effective amount of an anti-wear agent.

111. An additive concentrate comprising about 20 to 80 wt. % lubricating oil and 20 to about 80 wt. % of an post-treated oil soluble reaction product which is a post-treated poly (C₅ -C₉ lactone) modified Mannich base according to claim 86.

112. The additive concentrate according to claim 111, wherein said post-treated oil soluble reaction product has been prepared by first reacting polymer (a) with amine (b) and aldehyde (c) to form a Mannich base intermediate, and then reacting said C₅ -C₉ lactone (d) with said Mannich base intermediate, and then post-treating with a boron compound.

113. The concentrate according to claim 111, which also contains an effective amount of a viscosity modifier.

114. The concentrate according to claim 113, which also contains an effective amount of an antiwear agent.

115. The concentrate according to claim 112 wherein said boron compound comprises a member selected from the group consisting of a boron oxide, boron oxide hydrate, boron halide, boron ester and boron acid.

116. The concentrate according to claim 112, wherein said lactone is E-caprolactone, and wherein said post-treated oil soluble reaction product contains, on the average, from 1 to 20 caprolactone moieties per molecule of said monoolefin polymer.

117. An additive concentrate according to claim 116, which also contains an effective amount of a viscosity modifier.

118. An additive concentrate according to claim 117, which also contains an effective amount of a zinc dihydrocarbyl dithiophosphate.

119. An additive concentrate according to claim 118, wherein said post-treated oil soluble reaction product has been post-treated with a boron compound selected from the group consisting of a boron oxide, boron oxide hydrate, boron halide, boron ester and boron acid.