Lactone modified adducts or reactants and oleaginous compositions containing same

• US 4,954,276 A
• Filed: 08/31/1989
• Issued: 09/04/1990
• 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): Dixon, Jr., William R.
• Assistant Examiner(s): Johnson, Jerry D.
• Application Number:
  US07/401,603
• Time in Patent Office: 369 Days
• Field of Search: 252/49.6, 525/285, 525/333.7, 525/337, 525/386, 525/388, 525/382
• US Class Current: 508/190
• CPC Class Codes: C08G 63/60 derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
• 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: C10M 129/95 Esters
• CPC Class Codes: C10M 133/52 having a carbon chain of 30 or more atoms
• 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 2207/144 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 2215/042 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 2215/26 : Amines
• CPC Class Codes: C10M 2215/28 : Amides; Imides
• CPC Class Codes: C10M 2215/30 : Heterocyclic compounds
• 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 2219/087 : 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 2223/04 : 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 2227/09 : 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 2070/02 : Concentrating of additives

Abstract

C₅ -C₉ lactone based adduct materials are made by reacting a C₅ -C₉ lactone with a polyamine, a polyol or an amino alcohol to form a lactone adduct intermediate, and thereafter reacting the intermediate with a hydrocarbyl substituted C₄ -C₁₀ monounsaturated dicarboxylic acid producing material, e.g., a polyisobutenyl succinimide, which, in turn, preferably was made by reacting a polymer of a C₂ to C₁₀ monoolefin, preferably polyisobutylene, having a molecular weight of about 300 to 10,000 with a C₄ to C₁₀ monounsaturated acid, anhydride or ester, preferably maleic anhydride, such that there are 0.7 to 2.0 dicarboxylic acid producing moieties per molecule of said olefin polymer used in the reaction mixture. The resulting adduct material are useful per se, as oil soluble dispersant additives, and are useful in fuel and lubricating oil compositions including concentrates containing the additives.

Claims

1. A C₅ -C₉ lactone adduct material useful as an oil additive and formed by first reacting at a temperature of from about 100 to about 250°

C. for a period of from about 1 to about 10 hours a hydrocarbyl substituted C₄ -C₁₀ dicarboxylic acid producing material (I) with the reaction product (II) of a C₅ -C₉ lactone with a member selected from the group consisting of (a) a polyamine having from about 2 to 60 total carbon atoms and from about 2 to about 12 nitrogen atoms, (b) an aliphatic polyhydric alcohol containing up to about 100 carbon atoms and from about 2 to about 10 10 hydroxyl groups, (c) an amino alcohol containing up to about 50 total carbon atoms, from 1 to about 3 nitrogen atoms and from 1 to about 15 hydroxyl groups, or (d) mixtures thereof, and then post-treating the reaction product of (I) and (II) with a boron compound;

said reaction product (II) being prepared at a temperature of from about 30 to about 200°

C. when said C₅ -C₉ lactone is reacted with said polyamine and at a temperature of about 50 to about 200°

C. when said C₅ -C₉ lactone is reacted with said aliphatic polyhydric alcohol or with said amino alcohol, said hydrocarbyl substituted acid producing material being formed by reacting an olefin polymer of a C₂ -C₁₀ monoolefin having a number average molecular weight of about 300 to about 10,000 and a C₄ -C₁₀ monousaturated dicarboxylic acid material selected from the group consisting of acids, esters and anhydrides and containing an average of from about 0.7 to about 2.0 moles of dicarboxylic acid producing material per mole of said olefin polymer used in the reaction, said adduct having, on the average, a degree of polymerization of C₅ -C₉ lactone of less than about 100.

2. The C₅ -C₉ lactone adduct material of claim 1, wherein said olefin polymer is polyisobutylene.

3. The C₅ -C₉ lactone adduct material of claim 2, wherein said lactone is E-caprolactone.

4. The C₅ -C₉ lactone adduct material of claim 3, wherein said C₄ -C₁₀ monounsaturated dicarboxylic acid material is maleic anhydride.

5. The C₅ -C₉ lactone adduct material of claim 4, wherein there are about 1 to about 1.5 succinic anhydride units per polyisobutenyl moiety present in said hydrocarbyl substituted C₄ -C₁₀ dicarboxylic acid producing material and wherein the number average molecular weight of said polyisobutylene is from about 500 to about 3,000.

6. The C₅ -C₉ lactone adduct material of claim 1, wherein said C₅ -C₉ lactone is reacted with a polyamine, and wherein said polyamine is an aliphatic saturated amine having the formula:

##STR11## 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.

7. The C₅ -C₉ lactone adduct material of claim 6, 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.

8. The C₅ -C₉ lactone adduct material of claim 1, wherein said amine is selected from the group consisting of alicyclic diamines, imidazolines, morpholines, and N-aminoalkyl piperazines of the general formula:

##STR12## wherein G is independently selected from the group consisting of hydrogen and omega(nontertiary)-aminoalkylene radicals of from 1 to 3 carbon atoms, and p is a number of from 1 to 4.

9. The C₅ -C₉ lactone adduct material of claim 1, wherein said amine is a mixture of poly (ethyleneamines) averaging about 5 to about 7 nitrogen atoms per molecule.

10. The C₅ -C₉ lactone adduct material of claim 1, wherein said amine is a polyoxyalkylene polyamine having the formula:

NH₂ --alkylene--(O--alkylene)_m --NH₂

wherein 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

wherein n has a value of about 1 to 40 with the provision 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 10 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.

11. The C₅ -C₉ lactone adduct material of claim 5, wherein said C₅ -C₉ lactone is reacted with a polyamine, and wherein said polyamine is an aliphatic saturated amine having the formula:

##STR13## wherein R and R40 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.

12. The C₅ -C₉ lactone adduct material of claim 11, 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.

13. The C₅ -C₉ lactone adduct material of claim 5, wherein said amine is selected from the group consisting of alicyclic diamines, imidazolines, morpholines, and N-aminoalkyl piperazines of the general formula:

##STR14## wherein G is independently selected from the group consisting of hydrogen and omega-(nontertiary)aminoalkylene radicals of from 1 to 3 carbon atoms, and p is a number of from 1 to 4.

14. The C₅ -C₉ lactone adduct material of claim 5, wherein said amine is a mixture of poly (ethyleneamines) averaging about 5 to about 7 nitrogen atoms per molecule.

15. The C₅ -C₉ lactone adduct material of claim 5, wherein said amine is a polyoxyalkylene polyamine having the formula:

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

wherein 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

wherein n has a value of about 1 to 40 with the provisions that the sum of all the n'"'"'s is from about 3 to about 60, R is a substituted saturated hydrocarbon radical of up to 10 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.

16. The C₅ -C₉ lactone adduct material of claim 1, wherein said C₅ -C₉ lactone is reacted with a polyhydric alcohol.

17. The C₅ -C₉ lactone adduct material of Claim 16, wherein said polyhydric alcohol is an aliphatic alcohol containing from 3 to 15 carbon atoms and at least three hydroxyl groups.

18. The C₅ -C₉ lactone adduct material of claim 17, wherein said polyhydric alcohol is a member selected from the group consisting of glycerol, erythritol, pentaerythritol, mannitol, sorbitol, 1,2,4 - hexanetriol and tetrahydroxy pentane.

19. The C₅ -C₉ lactone adduct material of claim 5, wherein said C₅ -C₉ lactone is reacted with a polyhydric alcohol.

20. The C₅ -C₉ lactone adduct material of claim 19, wherein said polyhydric alcohol is an aliphatic alcohol containing from 3 to 15 carbon atoms and at least three hydroxyl groups.

21. The C₅ -C₉ lactone adduct material of claim 20, wherein said polyhydric alcohol is a member selected from the group consisting of glycerol, erythritol, pentaerythritol, mannitol, sorbitol, 1,2,4-hexanetriol and tetrahydroxy pentane.

22. The C₅ -C₉ lactone adduct material of claim 1, wherein said C₅ -C₉ lactone is reacted with an amino alcohol.

23. The C₅ -C₉ lactone adduct material of claim 22, wherein said amino alcohol is a 2,2-disubstituted-2-amino-1-alkanol of the formula ##STR15## wherein X is alkyl or hydroxyalkyl group with the alkyl groups having from 1 to 3 carbon atoms, wherein at least one of the X substituents is a hydroxyalkyl group of the formula (CH₂)_n OH, and wherein n is 1 to 3.

24. The C₅ -C₉ lactone adduct material of claim 23, wherein said amino alcohol is tris (hydroxymethyl) amino methane.

25. The C₅ -C₉ lactone adduct material of claim 5, wherein said C₅ -C₉ lactone is reacted with an amino alcohol.

26. The C₅ -C₉ lactone adduct material of claim 25, wherein said amino alcohol is a 2,2-disubstituted-2-amino-1-alkanol of the formula:

##STR16## wherein X is alkyl or hydroxyalkyl group with the alkyl groups having from 1 to 3 carbon atoms, wherein at least one of the X substituents is a hydroxyalkyl group of the formula (CH₂)_n OH, and wherein n is 1 to 3.

27. The C₅ -C₉ lactone adduct material of claim 26, wherein said amino alcohol comprises tris (hydroxymethyl) amino methane.

28. The C₅ -C₉ lactone adduct material of claim 1, wherein said post-treating of the reaction product of (I) and (II) has been carried out with a borating agent selected from the group consisting of boron oxide, boron oxide hydrate, boron halides, boron esters and boron acids.

45. A lubricating oil composition comprising lubricating oil and about 0.01 to 15 wt. % of the C₅ -C₉ lactone adduct material of claim 3.

46. A lubricating oil comprising a major amount of lubricating oil and about 0.1 to 10 wt. % of the C₅ -C₉ lactone adduct material of claim 3.

47. A lubricating oil comprising a major amount of lubricating oil and about 0.01 to 15 wt. % of the C₅ -C₉ lactone adduct material of claim 5.

48. A lubricating oil comprising a major amount of lubricating oil and about 0.01 to 15 wt. % of the C₅ -C₉ lactone adduct material of claim 24.

49. A lubricating oil comprising a major amount of lubricating oil and about 0.01 to 15 wt. % of the C₅ -C₉ lactone adduct material of claim 18.

50. A lubricating oil comprising a major amount of lubricating oil and about 0.1 to 10 wt. % of the C₅ -C₉ lactone adduct material of claim 6.

51. A lubricating oil comprising a major amount of lubricating oil and about 0.1 to 10 wt. % of the C₅ -C₉ lactone adduct material of claim 9.

52. A lubricating oil comprising a major amount of lubricating oil about 0.1 to 10 wt. % of the caprolactone adduct material of claim 17.

53. A lubricating oil comprising a major amount of lubricating oil and about 0.1 to 10 wt. % of the caprolactone adduct material of claim 23.

54. A lubricating oil comprising a major amount of lubricating oil and about 0.1 to 10 wt. % of the caprolactone adduct material of claim 11.

55. A lubricating oil comprising a major amount of lubricating oil and about 0.1 to 10 wt. % of the caprolactone adduct material of claim 14.

56. A lubricating oil comprising a major amount of lubricating oil and about 0.01 to 15 wt. % of the C₅ -C₉ lactone adduct material of claim 28.

29. An oleaginous composition comprising (I) a lubricating oil and (II) a borated C₅ -C₉ lactone adduct material, said adduct material being prepared by first reacting (i) a C₅ -C₉ lactone with (ii) a member selected from the group consisting of (a) a polyamine having from about 2 to about 60 total carbon atoms and from about 2 to about 12 nitrogen atoms, (b) an aliphatic polyhydric alcohol containing up to about 100 total carbon atoms and from about 2 to about 10 hydroxyl groups, and (c) an amino alcohol containing up to about 50 total carbon atoms, from 1 to about 3 nitrogen atoms and from 1 to about 15 hydroxyl groups, and (d) mixtures of (a), (b) and (c) to form an intermediate lactone adduct, then reacting said intermediate lactone adduct with (iii) a hydrocarbyl substituted C₄ -C₁₀ dicarboxylic acid producing material selected form the group consisting of acids, esters and anhydrides to form a C₅ -C₉ lactone adduct material, and then with a borating agent to form said borated C₅ -C₉ lactone adduct material;

said reaction between said C₅ -C₉ lactone material and said polyamine being carried out at a temperature of from about 30 to about 200°

C.;

said reaction between said C₅ -C₉ lactone and said polyhydric alcohol or said amino alcohol being carried out at a temperature of from about 50 to about 200°

C.;

said reaction between said intermediate lactone adduct and said hydrocarbyl substituted C₄ -C₁₀ dicarboxylic acid producing material being conducted at a temperature of from about 100 to about 250°

C. for a period of from about 1 to about 10 hours;

said hydrocarbyl substituted C₄ -C₁₀ dicarboxylic acid producing material being formed by reacting an olefin polymer of a C₂ -C₁₀ monoolefin having a number average molecular weight of from about 300 to about 10,000 with a C₄ -C₁₀ monounsaturated dicarboxylic acid material and containing an average of from about 0.7 to about 2.0 moles of dicarboxylic acid producing material per mole of said olefin polymer used in the reaction; and

said C₅ -C₉ lactone adduct material having, on the average, a degree of polymerization of C₅ -C₉ lactone of less than about 100.

30. The oleaginous composition of claim 29, wherein said olefin polymer is polyisobutylene.

31. The oleaginous composition of claim 30, wherein said lactone is E-caprolactone.

32. The oleaginous composition of claim 31, wherein said C₄ -C₁₀ monousaturated dicarboxylic acid material is maleic anhydride.

33. The oleaginous composition of claim 32, wherein there are about 1 to about 1.5 succinic anhydride units per polyisobutenyl moiety present in said hydrocarbyl substituted C₄ -C₁₀ dicarboxylic acid producing material and wherein the number average molecular weight of said polyisobutylene is from about 500 to about 3,000.

34. The oleaginous composition of claim 33, wherein said C₅ -C₉ lactone is reacted with a polyamine, and wherein said polyamine is an aliphatic saturated amine having the formula:

##STR17## 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.

35. The oleaginous composition of claim 34, 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.

36. The oleaginous composition of claim 33, wherein said amine is selected from the group consisting of cyclic diamines, imidazolines, morpholines, and N-aminoalkyl piperazines of the general formula:

##STR18## wherein G is independently selected from the group consisting of hydrogen and omega-nontertiary)-aminoalkylene radicals of from 1 to 3 carbon atoms, and p is a number of from 1 to 4.

37. The oleaginous composition of claim 33, wherein said amine is a mixture of poly (ethyleneamines) averaging about 5 to about 7 nitrogen atoms per molecule.

38. The oleaginous composition of claim 33, wherein said amine is a polyoxyalkylene polyamine having the formula:

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

wherein 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

wherein n has a value of about 1 to 40 with the provision 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 10 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.

39. The oleaginous composition of claim 33, wherein said C₅ -C₉ lactone is reacted with a polyhydric alcohol.

40. The oleaginous composition of claim 39, wherein said polyhydric alcohol is an aliphatic alcohol containing from 3 to 15 carbon atoms and at least three hydroxyl groups.

41. The oleaginous composition of claim 40, wherein said polyhydric alcohol is a member selected from the group consisting of glycerol, erythritol, pentaerythritol, mannitol, sorbitol, 1,2,4-hexanetriol and tetrahydroxy pentane.

42. The oleaginous composition of claim 33, wherein said C₅ -C₉ lactone is reacted with an amino alcohol.

43. The oleaginous composition of claim 42, wherein said amino alcohol is a 2,2-disubstituted-2-amino-1-alkanol of the formula ##STR19## wherein X is alkyl or hydroxyalkyl group with the alkyl groups having from 1 to 3 carbon atoms, wherein at least one of the X substituents is a hydroxyalkyl group of the formula --CH₂)_n OH, and wherein n is 1 to 3.

44. The oleginous composition of claim 43, wherein said amino alcohol comprises tris (hydroxymethyl) amino methane.

57. An oil soluble dispersant useful as an oil additive, comprising the product of a reaction mixture comprising (A) a borating agent and (B) the product of a reaction mixture ecomprising as reactants:

(I) a hydrocarbyl substituted C₄ -C₁₀ monounsaturated dicarboxylic acid producing material formed by reacting olefin polymer of C₂ to C₁₀ monoolefin having a number average molecular weight of about 300 to 10,000 and a C₄ to C₁₀ monounsaturated acid material selected from the group consisting of acids, esters and anhydrides, wherein said hydrocarbyl substituted C₄ -C₁₀ monousaturated dicarboxylic acid producing material contains from about 0.7 to about 2.0 moles of dicarboxylic acid producing material per mole of said olefin polymer in the reaction mixture; and

(II) a C₅ -C₉ lactone adduct formed by reacting (a) a C₅ -C₉ lactone with (b) a member selected from the group consisting of (i) a polyamine having from about 2 to 60 total carbon atoms and from about 2 to about 12 nitrogen atoms, (ii) an aliphatic polyhydric alcohol containing up to about 100 total carbon atoms and from about 2 to about 10 hydroxyl groups, (iii) an amino alcohol containing up to about 50 total carbon atoms, from 1 to about 3 nitrogen atoms and from 1 to about 15 hydroxyl groups, and (iv) mixtures of (i), (ii), and (iii), wherein there are from about 0.2 to about 50 molar equivalents of C₅ -C₉ lactone derived moieties per molar equivalent of said adduct (II) used in the reaction, the reaction between reactants (I) and (II) having been conducted at a temperature of from about 100°

to about 250°

C. for a period of from about 1 to about 10 hours.

58. An oil soluble dispersant according to claim 57, wherein said C₅ -C₉ lactone is caprolactone.

59. An oil soluble dispersant according to claim 58, wherein said caprolactone is reacted with a polyamine.

60. An oil soluble dispersant according to claim 59, wherein said polyamine is an aliphatic saturated amine having the general formula ##STR20## wherein R and R'"'"' independently are selected from the group consisting of hydrogen:

C₁ to C₂₅ straight of 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 of secondary amino groups.

61. An oil soluble dispersant according to claim 60, wherein said polyamine is selected from the roup 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.

62. The oil soluble dispersant of claim 59, wherein said polyamine is selected from the group consisting of alicyclic diamines, imidazoles, morpholines, and N-aminoalkyl piperazines of the general formula:

##STR21## wherein G is independently selected from the group consisting of hydrogen and omega-(nontertiary)-aminoalkylene radicals of from 1 to 3 carbon atoms, and p is a number of from 1 to 4.

63. The oil soluble dispersant of claim 59, wherein said polyamine is a mixture of poly(ethyleneamines) averaging about 5 to about 7 nitrogen atoms per molecule.

64. An oil soluble dispersant according to claim 59, 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

wherein n has value of about 1 to 40 with the provision 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 10 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.

65. An oil soluble dispersant according to claim 58, wherein said caprolactone is reacted with a polyhydric alcohol.

66. An oil soluble dispersant according to claim 65, wherein said polyhydric alcohol is an aliphatic alcohol containing from 3 to 15 carbon atoms and at least three hydroxyl groups.

67. An oil soluble dispersant according to claim 66, wherein said polyhydric alcohol is a member selected from the group consisting of glycerol, erythritol, pentaerythritol, mannitol, sorbitol, 1,2,4-hexanetriol and tetrahydroxy pentane.

68. An oil soluble dispersant according to claim 58, wherein said caprolactone is reacted with an amino alcohol.

69. An oil soluble dispersant according to claim 68, wherein said amino alcohol is a 2,2-disubstituted-2-amino-1-alkanol of the formula ##STR22## wherein X is a alkyl or hydroxyalkyl group with the alkyl groups having from 1 to 3 carbon atoms, wherein at least one of the X substituents is a hydroxyalkyl group of the formula --CH₂)_n OH, and wherein n is 1 to 3.

70. An oil soluble dispersant according to claim 69, wherein said amino alcohol is tris(hydroxymethyl)amino methane.

71. An oil soluble dispersant according to claim 58, wherein the reaction product of I and II has been post-treated with a borating agent selected from the group consisting of boron oxide, boron oxide hydrate, boron halides, boron esters and boron acids.

72. An oil soluble reaction product useful as an oil additive, comprising:

(a) polymer consisting essentially of C₂ to C₁₀ monoolefin, said polymer being of 300 to 10,000 number average molecular weight and being substituted with succinic moieties selected from the group consisting of acid, anhydride and ester groups, wherein there are about 0.7 to about 2.0 molar proportions of succinic moieties per molar proportion of said polymer,

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

(c) C₅ -C₉ lactone, and

(d) boron,

wherein (b) is first reacted with (c) at a temperature of from about 30 to about 200°

C., wherein the resulting product of (b) and (c) is then reacted with (a) at a temperature of from about 100 to about 250°

C. for a period of from about 1 to about 10 hours, wherein the resulting product of (a), (b) and (c) is then reacted with a borating agent, and wherein there are from about 2.0 to about 100 molar proportions of (c) per molar proportion of said reaction product.

73. The oil soluble reaction product according to claim 72 wherein (a) is polyisobutylene of about 500 to 3,000 number average molecular weight substituted with succinic anhydride moieties, wherein (c) is E-caprolactone, and wherein there are about 0.5 to 20 molar proportions of (c) per molar proportion of said reaction product.

74. An oil soluble reaction product useful as an oil additive, comprising:

(a) polymer consisting essentially of C₂ to C₁₀ monoolefin said polymer being of 300 to 10,000 number average molecular weight and being substituted with succinic moieties selected from the group consisting of acid, anhydride and ester groups wherein there are from about 0.7 to about 2.0 molar proportions of succinic moieties per molar proportion of said polymer,

(b) aliphatic polyhydric alcohol containing up to about 100 total carbon atoms and from 2 to about 10 hydroxyl groups,

(c) C₅ -C₉ lactone, and

(d) boron,

wherein (b) is first reacted with (c) at a temperature of form about 50 to about 200°

C., wherein the resulting product of (b) and (c) is then reacted with (a) at a temperature of from about 100 to about 250°

C. for a period of from about 1 to about 10 hours, wherein the resulting product of (a), (b) and (c) is then reacted with a borating agent, and wherein there are from about 0.2 to about 100 molar proportions of (c) per molar proportion of said reaction product.

75. The oil soluble reaction product according to claim 74 wherein (a) is polyisobutylene of about 500 to 3,000 number average molecular weight substituted with succinic anhydride moieties, wherein (c) is E-caprolactone, and wherein there are about 0.5 to 20 molar proportions of (c) per molar proportion of said reaction product.

76. An oil soluble reaction product useful as an oil additive, comprising:

(a) polymer consisting essentially of C₂ to C₁₀ monoolefin said polymer being of 300 to 10,000 number average molecular weight and being substituted with succinic moieties selected from the group consisting of acid, anhydride and ester groups wherein there are about 0.7 to 2.0 molar proportions of succinic moieties per molar proportion of said polymer,

(b) amino alcohol containing up to about 50 total carbon atoms, from 1 to about 3 nitrogen atoms and from 1 to about 15 hydroxyl groups,

(c) C₅ -C₉ lactone, and

(d) boron,

wherein (b) is first reacted with (c) at a temperature of from about 50 to about 200°

C., wherein the resulting product of (b) and (c) is then reacted with (a) at temperature of from about 100 to about 250°

C. for a period of from about 1 to about 10 hours, wherein the resulting product of (a), (b) and (c) is then reacted with a borating agent, and wherein there are from about 0.2 to about 100 molar proportions of (c) per molar proportion of said reaction product.

77. The oil soluble reaction product according to claim 76 wherein (a) is polyisobutylene of about 500 to 3,000 number average molecular weight substituted with succinic anhydride moieties, wherein (c) is E-caprolactone, and wherein there are about 0.5 to 20 molar proportions of (c) per molar proportion of said reaction product.

79. A lubricating oil composition according to claim 76, wherein (a) is caprolactone, and wherein the degree of polymerization of said caprolactone in said oil soluble additive is from about 5 to about 20.

80. A lubrication oil composition according to claim 79, wherein (II) is polyisobutylene of about 500 to 3,000 number average molecular weight substituted with succinic anhydride moieties.

81. A lubricating oil composition according to claim 80, wherein said borating agent III is selected form the group consisting of boron oxide, boron oxide hydrate, boron halides, boron esters and boron acids.

78. A lubricating oil composition comprising a lubricating oil and a boron-containing oil soluble additive;

said additive being the reaction of product of (I) a C₅ -C₉ lactone adduct, (II) a polymer of a C₂ to C₁₀ monoolefin having a number average molecular weight of about 300 to about 10,000 and a C₄ -C₁₀ monousaturated dicarboxylic acid material, wherein there are an average of from about 0.7 to about 2.0 dicarboxylic acid producing moieties per molecular equivalent of said polymer, and (III) a borating agent, wherein (I) is first reacted with (II) at a temperature of from about 100 to about 250°

C. for a period of from about 1 to about 10 hours, and the resulting product of (I) and (II) is then reacted with said borating agent;

said C₅ -C₉ lactone adduct (I) being prepared by reacting (a) a C₅ -C₉ lactone with (b) at least one member selected from the group consisting of (i) a polyamine having from about 2 to 60 total carbon atoms and from a bout 2 to about 12 nitrogen atoms, (ii) an aliphatic polyhydric alcohol containing up to about 100 total carbon atoms and from about 2 to about 10 hydroxyl groups, (iii) an amino alcohol containing up to about 50 total carbon atoms, from 1 to about 3 nitrogen atoms and from 1 to about 15 hydroxyl groups;

wherein the reaction of (a) and (b) is conducted at a temperature of from about 30 to about 200°

C. when (a) is reacted with (b) (i) and at a temperature of from about 50 to about 200°

C. when (a) is reacted with (b)(ii) or (b)(iii);

wherein there are on the average, from about 0.2 to about 100 molar proportions of (a) per molar proportion of (b) in said C₅ -C₉ lactone adduct; and

wherein said additive has, on the average, a degree of polymerization of C₅ -C₉ lactone of less than about 100.

82. 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 a borated dispersant formed by post-treating with a borating agent a dispersant formed by reacting at a temperature of from about 100 to about 250°

C. for a period of from about 1 to about 10 hours a polyolefin substituted with succinic acid or anhydride moieties with the reaction product of a C₅ -C₉ lactone and at least one member selected from the group consisting of polyamines having from about 2 to 60 total carbon atoms and from about 2 to about 12 nitrogen atoms, aliphatic polyhydric alcohols containing up to about 100 total carbon atoms and from about 2 to about 10 hydroxyl groups, and amino alcohols containing up to about 50 total carbon atoms, from 1 to about 3 nitrogen atoms and from 1 to about 15 hydroxyl groups, wherein said reaction product is prepared at a temperature of from about 30 to about 200°

C. when said C₅ -C₉ lactone is reacted with a polyamine and at a temperature of from about 50 to about 200°

C. when said C₅ -C₉ lactone is reacted with a polyhydric alcohol or with an amino alcohol, wherein said substituted succinic acid or anhydride has from about 0.7 to about 2.0 molar proportions of succinic moieties per molar proportion of polyolefin, wherein said polyolefin is a polymer of C₂ to C₁₀ monoolefin having a number average molecular weight of about 300 to 10000, and wherein said dispersant has from about 0.2 to about 100 molar proportions of lactone moieties per molar proportion of polyolefin; and

an effective amount of a viscosity modifier.

83. A composition according to claim 82, wherein said polyolefin is polyisobutylene and wherein said C₅ -C₉ lactone is caprolactone.

84. A composition according to claim 83, wherein said composition also contains an anti-wear effective amount of a zinc dihydrocarbyl dithiophosphate.

85. An additive concentrate comprising about 20 to 80 wt. % lubricating oil and 20 to 80 wt. % of a borated dispersant which is a C₅ -C₉ lactone adduct material formed by first reacting from about 0.2 to about 100 molar proportions of a C₅ -C₉ lactone per molar proportion of at least one member selected from the group consisting of polyamines having from about 2 to 60 total carbon atoms and from about 2 to about 12 nitrogen atoms, aliphatic polyhydric alcohol containing up to about 100 total carbon atoms and from about 2 to about 10 hydroxyl groups, and amino alcohols containing up to about 50 total carbon atoms, from 1 to about 3 nitrogen atoms and from 1 to about 15 hydroxyl groups, to form a lactone adduct intermediate, then reacting said intermediate with a hydrocarbyl substituted C₄ to C₁₀ mono-unsaturated dicarboxylic acid producing material to form a dispersant, and then reacting said dispersant with a borating agent to form said borated dispersant, wherein the reaction between said lactone and a polyamine is conducted at a temperature of from about 30 to about 200°

C., wherein the reaction between said lactone and a polyhydric alcohol or an amino alcohol is conducted at a temperature of from about 50 to about 200°

C., wherein the reaction between the lactone intermediate and the hydrocarbyl substituted dicarboxylic acid producing material is carried out at a temperature of from about 100 to about 250°

C. for a period of from about 1 to about 10 hours, wherein the hydrocarbyl substituted dicarboxylic acid producing material is formed by reacting an olefin polymer of a C₂ to C₁₀ monoolefin having a number average molecular weight of about 300 to 10,000 with a C₄ to C₁₀ monounsaturated acid material, wherein said hydrocarbyl substituted dicarboxylic acid producing material contains an average of from about 0.7 to about 2.0 dicarboxylic acid producing moieties per molar equivalent of said olefin polymer, and wherein the borated dispersant has, on the average, a degree of polymerization of C₅ -C₉ lactone of less than about 100.

86. A concentrate according to claim 85, wherein said borated dispersant is formed by reacting a polyisobutylene with maleic anhydride, then reacting the polyisobutylene-maleic anhydride reaction product with said C₅ -C₉ lactone adduct intermediate to form said dispersant, and then reacting said dispersant with a borating agent selected form the group consisting of boron oxide, boron oxide hydrate, boron halides, boron esters and boron acids.

87. A concentrate according to claim 86, wherein said C₅ -C₉ lactone is caprolactone and which also contains an effective amount of a viscosity improver.

88. A concentrate according to claim 87, which also contains an anti-wear effective amount of a zinc dihydrocarbyl dithiophosphate.

89. An additive concentrate comprising about 20 to 80 wt. % lubricating oil and about 20 to 80 wt. % of an oil soluble borated reaction product of a caprolactone adduct, (b) a hydrocarbyl substituted C₄ to C₁₀ monounsaturated dicarboxylic acid producing material, and (c) a borating agent;

said hydrocarbyl substituted material being formed by reacting an olefin polymer of a c₂ to C₁₀ monoolefin having a number average molecular weight of about 500 to 3,000 and a C₄ to C₁₀ monounsaturateed acid or anhydride and containing from about 0.7 to about 2.0 dicarboxylic acid producing moieties per molar equivalent of said olefin polymer;

said caprolactone adduct containing form 0.5 to 20 caprolactone moieties per molar equivalent of said olefin polymer present in said reaction product and being prepared by reacting caprolactone with at least one member selected from the group consisting of polyamines having from about 2 to 60 total carbon atoms and from about 2 to about 12 nitrogen atoms, aliphatic polyhydric alcohol containing up to about 100 total carbon atoms and from about 2 to about 10 hydroxyl groups, and amino alcohols containing up to about 50 total carbon atoms, from 1 to about 3 nitrogen atoms and from 1 to about 15 hydroxyl groups;

wherein the reaction between said caprolactone and a polyamine being conducted at a temperature of from about 30 to about 100°

C. and the reaction between said caprolactone and a polyhydric alcohol or amino alcohol being conducted at a temperature between about 50 and about 200°

C.; and

wherein said caprolactone and said hydrocarbyl substituted material are reacted at a temperature of from about 100 to about 250°

C. for a period of from about 1 to about 10 hours prior to being reacted with said borating agent.

90. An additive concentrate according to claim 89, wherein said hydrocarbyl substituted C₄ to C₁₀ acid producing material is polyisobutylene substituted with 1 to 1.5 moles of succinic anhydride units per mole of polyisobutylene.

91. An additive concentrate according to claim 90, wherein said borating agent is selected from the group consisting of boron oxide, boron oxide hydrate, boron halides, boron esters and boron acids.