Lactone modified dispersant additives useful in oleaginous compositions

• US 4,943,382 A
• Filed: 04/06/1988
• Issued: 07/24/1990
• Est. Priority Date: 04/06/1988
• 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.
• Application Number:
  US07/178,100
• Time in Patent Office: 839 Days
• Field of Search: 252/51.5 A, 548/520, 548/546
• US Class Current: 508/291
• CPC Class Codes: C08F 10/00 Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
• CPC Class Codes: C08F 2810/20 leading to a crosslinking, either explicitly or inherently
• CPC Class Codes: C08F 8/16 Lactonisation
• 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: C10L 1/221 compounds of uncertain formula; reaction products where mixtures of compounds are obtained
• CPC Class Codes: C10M 129/20 Cyclic ethers having 4 or more ring atoms, e.g. furans, dioxolanes
• 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 2207/044 Cyclic ethers having four or more ring atoms, e.g. furans, dioxolanes
• 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 2215/24 : 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 2217/046 : 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 2219/085 : 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 2221/00 : Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
• CPC Class Codes: C10M 2223/045 : Metal containing thio derivatives
• CPC Class Codes: C10M 2223/12 : obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
• CPC Class Codes: C10M 2225/04 : obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
• CPC Class Codes: C10M 2225/041 : Hydrocarbon polymers
• CPC Class Codes: C10M 2227/00 : Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
• CPC Class Codes: C10M 2227/09 : Complexes with metals
• CPC Class Codes: C10M 2229/041 : containing aliphatic substituents
• CPC Class Codes: C10N 2010/04 : 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 fueled engines
• CPC Class Codes: C10N 2040/252 : Diesel engines
• CPC Class Codes: C10N 2040/253 : Small diesel engines
• CPC Class Codes: C10N 2040/255 : Gasoline engines
• CPC Class Codes: C10N 2040/28 : Rotary engines
• CPC Class Codes: C10N 2070/02 : Concentrating of additives

Abstract

Lactone modified adducts are made by first reacting a non-polymerizable lactone or thiolactone and then a polymerizable C₅ -C₉ lactone with an aminated hydrocarbyl substituted C₄ -C₁₀ monounsaturated dicarboxylic acid producing material, e.g. a polyisobutenyl succinimide, 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 5,000 with a C₄ to C₁₀ monounsaturated acid, anhydride or ester, preferably maleic anhydride, such that there are about 0.7 to 2.0 dicarboxylic acid producing moieties per molecule of said olefin polymer used in the reaction mixture, and then reacting the substituted acid, anhydride or ester with an amine. 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 lactone modified adduct of an aminated, hyrdocarbyl substituted C₄ -C₁₀ dicarboxylic acid producing material useful as an oil additive and formed by first reacting a non-polymerizable lactone selected from the group consisting of lactones and thiolactones having up to four carbon atoms in the lactone ring with an aminated, hyrdocarbyl substituted C₄ -C₁₀ dicarboxylic acid producing material to form an intermediate adduct, and then, in a separate step, reacting said intermediate adduct with a C₅ -C₉ polymerizable lactone at a temperature of from about 30°

to about 200°

C. for a period sufficient to effect ring opening polymerization of said C₅ -C₉ lactone to form the lactone modified adduct acid producing material being formed by reacting an olefin polymer of a C₂ -C₁₀ monoolefin having a number average molecular weight of about 700 to about 5,000 and a C₄ -C₁₀ monounsaturated dicarboxylic acid material, wherein there is an average of 0.7 to about 2.0 sicarboxylic producing moieties per molecule of said olefin polymer used in the reaction, said aminated hydrocarbyl substituted C₄ -C₁₀ dicarboxylic acid producing material having been aminated with a non-heterocyclic amine 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, and said lactone modified adduct product containing the unit ##STR12## wherein m represents the average degree of polymerization and has a average value of from 0.2 to about 100 and q is 4 to 8.

2. The lactone modified additive material according to claim 1, wherein said C₅ -C₉ polymerizable lactone is E-caprolactone.

3. The lactone modified adduct material according to claim 1, wherein said non-polymerizable lactone is butyrolactone.

4. The lactone modified adduct material according to claim 2, wherein said non-polymerizable lactone is butyrolactone.

5. The lactone modified adduct material according to claim 1, wherein said C₄ -C₁₀ dicarboxylic acid producing material is maleic anhydride.

6. The lactone modified adduct material according to claim 4, wherein said C₄ -C₁₀ dicarboxylic acid producing material is maleic anhydride.

7. The lactone modified adduct material according to claim 1, wherein said olefin polymer is polyisobutylene.

8. The lactone modified adduct material according to claim 2, wherein said olefin polymer is polyisobutylene.

9. The lactone modified adduct material according to claim 6, wherein said olefin polymer is polyisobutylene.

10. The lactone modified adduct material according to claim 9, wherein said amine is an aliphatic saturated amine having the formula ##STR13## 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.

11. The lactone modified adduct material of claim 10, 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.

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

13. The lactone modified adduct material of claim 9, wherein said amine is a polyoxyalkylene polyamine having the formula:

space="preserve" listing-type="equation">NH.sub.2 -alkylene -(0-alkylene)-.sub.m NH.sub.2

where m has a value of about 3 to 70;

or

space="preserve" listing-type="equation">R -[alkylene-(0-alkylene)-.sub.n NH.sub.2 ]a

where n has a value of about 1 to 40 with the provision that the sum of all the nos is from about 3 to about 70, R is a polyvalent saturated hydrocarbon radical of up to ten carbon atoms, and a is a number from 3 to 6.

14. The lactone modified adduct material of claim 9, wherein said amine is capable of reacting with said hydrocarbyl substituted acid producing material, in a cyclodehydration reaction, said amine having the generalized formula

15. The lactone modified adduct material according to claim 1, wherein the average value of m is 0.5 to about 20.

16. The lactone modified adduct material according to claim 4, wherein the average value of m is 0.5 to about 20.

17. The lactone modified adduct material according to claim 7, wherein the average value of m is 0.5 to about 20.

18. The lactone modified adduct according to claim 15, wherein there are about 0.7 to 2.0 succinic anhydride units per polyisobutylene moiety used in said reaction.

19. The lactone modified adduct according to claim 15, wherein there are about 1.0 to 1.5 succinic anhydride units per polyisobutylene moiety used in said reaction.

20. The lactone modified adduct according to claim 17, wherein there are about 0.7 to 2.0 succinic anhydride units per polyisobutylene moiety used in said reaction.

21. The lactone modified adduct according to claim 17, wherein there are about 1.0 to 1.5 succinic anhydride units per polyisobutylene moiety used in said reaction.

22. The lactone modified adduct according to claim 9, wherein there are about 0.7 to 2.0 succinic anhydride units per polyisobutylene moiety used in said reaction.

23. The lactone modified adduct according to claim 9, wherein there are about 1.0 to 1.5 succinic anhydride units per polyisobutylene moiety used in said reaction.

26. A lubricating oil composition comprising lubricating oil and about 0.01 to 15 wt. % of the lactone modified adduct material of claim 1.

27. A lubricating oil comprising a major amount of lubricating oil and about 0.1 to 10 wt. % of the lactone modified adduct material of claim 3.

28. A lubricating oil comprising a major amount of lubricating oil and about 0.1 to 10 wt. % of the lactone modified adduct material according to claim 4.

29. A lubricating oil comprising a major amount of lubricating oil and about 0.1 to 10 wt. % of the lactone modified adduct material according to claim 10.

30. A lubricating oil comprising a major amount of lubricating oil and about 0.1 to 7 wt. % of the lactone modified adduct material according to claim 10.

31. A lubricating oil comprising a major amount of lubricating oil and about 0.1 to 7 wt. % of the lactone modified adduct material according to claim 11.

32. A lubricating oil comprising a major amount of lubricating oil and about 0.1 to 10 wt. % of the lactone modified adduct material according to claim 17.

33. An oil composition containing 0.01 to 15 wt. %, based on the weight of the total composition, of a lactone modified adduct material according to claim 1.

34. An oil composition containing 0.01 to 15 wt. %, based on the weight of the total composition, of a lactone modified adduct material according to claim 4.

35. An oil composition containing 0.01 to 15 wt. %, based on the weight of the total composition, of a lactone modified adduct material according to claim 9.

24. An oleaginous composition comprising an oleaginous lubricating oil and a poly lactone modified adduct material prepared by first reacting a non-heterocyclic polyamine with a hydrocarbyl substituted C₄ -C₁₀ dicarboxylic acid producing material to form a neutralized reaction product having at least one reactive amino group, then reacting said neutralized reaction product with a non-polymerizable lactone selected from the group consisting of lactones and thiolactones having up to four carbon atoms in the lactone ring to form an intermediate adduct, and then, in a separate step, reacting said intermediate adduct with a C₅ -C₉ polymerizable lactone at a temperature of from about 30°

to about 200°

C. for a period sufficient to effect ring opening polymerization of said C₅ -C₉ lactone, said hydrocarbyl substituted C₄ -C₁₀ dicarboxylic acid producing material being formed by reacting an olefin polymer of a C₂ -C₁₀ monolefin of 700 to about 5,000 M_n with a C₄ -C₁₀ monounsaturated dicarboxylic acid material, wherein there is an average of from about 0.7 to about 2.0 dicarboxylic acid producing moieties per molecule of said olefin polymer used in the reaction, and wherein said lactone modified adduct material contains the unit ##STR14## where m represents the average degree of polymerization and is a number having an average value of from 0.2 to about 100 and q is 4 to 8, said lactone modified adduct material being useful as an oil additive.

25. The oleaginous composition according to claim 24, wherein said non-polymerizable lactone is butyrolactone and said polymerizable lactone is E-caprolactone.

36. An oil soluble dispersant useful as an oil additive, comprising the product of a reaction mixture comprising (I) and (II), which product is further reacted, in a separate step, with (III), wherein

(I) is the reaction product of (a) a hydrocarbyl substituted C₄ to C₁₀ monounsaturated dicarboxylic acid producing material formed by reacting olefin polymer of C₂ to C₁₀ monoolefin having a molecular weight of about 700 to 5,000 and a C₄ to C₁₀ monounsaturated acid material, wherein there are 0.7 to 2.0 dicarboxylic acid producing moieties per molecule of said olefin polymer in the reaction mixture, and (b) a non-heterocyclic polyamine;

and wherein

(II) is a non-polymerizable lactone selected from the group consisting of lactones and thiolactones having up to four carbon atoms in the lactone ring; and

wherein

(III) is a polymerizable C₅ -C₉ lactone, wherein there are, on the average, from about 0.2 to about 100 C₅ -C₉ lactone derived moieties per unit of said reaction product (I) used in the reaction and wherein said C₅ -C₉ lactone is reacted at a temperature of from about 30°

to about 200°

C. for a period sufficient to effect ring opening polymerization of said C₅ -C₉ lactone.

37. An oil soluble dispersant according to claim 36, wherein said non-polymerizable lactone is butyrolactone, said polymerizable C₅ -C₉ lactone is caprolactone, and said dispersant contains the unit ##STR15## wherein m is from 0.2 to about 100.

38. An oil soluble dispersant according to claim 36, 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.

39. An oil soluble dispersant according to claim 38, wherein m is 0.5 to 20, and said polyamine is an aliphatic saturated amine having the general formula ##STR16## 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.

40. An oil soluble dispersant according to claim 38, 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-(1,3propylene triamine;

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

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

N-dodecyl-1,3-propane diamine.

41. The oil soluble dispersant according to claim 37, wherein said polyamine is a mixture of poly (ethyleneamines) averaging about 5 to about 7 nitrogen atoms per molecule.

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

(a) polymer consisting essentially of C₂ to C₁₀ monoolefin, said polymer being of about 700 to 5,000 molecular weight and 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) non-heterocyclic polyamine containing 2 to 60 carbon atoms and 2 to 12 nitrogen groups, and

(c) non-polymerizable lactone selected from the group consisting of lactones and thiolactones having up to four carbon atoms in the lactone ring, and

(d) polymerizable C₅ -C₉ lactone, wherein

(a) is first reacted with (b), and the reaction product of (a) and (b) is then reacted with (c), and then the resulting reaction product of (a), (b) and (c) is reacted with (d) at a temperature of from about 30°

to about 200°

C. for a period sufficient to effect ring opening polymerization of said C₅ -C_b 9 lactone, and wherein there are, on the average, about 0.2 to 100 polar proportions of (d) per molar proportion of said reaction product.

43. The oil soluble reaction product according to claim 42, wherein (b) is an aliphatic saturated amine having the general 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.

44. The oil soluble reaction product according to Claim 42, wherein (b) 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.

45. The oil soluble reaction product according to claim 42, wherein (b) is a mixture of poly(ethyleneamines) averaging about 5 to about 7 nitrogen atoms per molecule.

46. The oil soluble reaction product according to claim 42, wherein (a) is polyisobutylene of about 700 to 3,000 molecular weight substituted with succinic anhydride moieties.

47. The oil soluble reaction product according to claim 42, wherein (c) is butyrolactone.

48. The oil soluble reaction product according to claim 42, wherein (d) is E-caprolactone and wherein there are about 0.5 to 20 molar proportions of (c) per molar proportion of said reaction product.

49. The oil soluble reaction product according to claim 47, wherein (d) is E-caprolactone and wherein there are about 0.5 to 20 molar proportions of (c) per molar proportion of said reaction product.

50. The oil soluble reaction product according to claim 49, wherein (a) is a polyisobutylene of about 900 to about 2,500 molecular weight substituted with succinic anhydride moieties.

51. The oil soluble reaction product according to claim 49, wherein (b) is an aliphatic saturated amine having the general formula ##STR18## 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'"'"' is H such that there are at least two of either primary or secondary amino groups.

52. The oil soluble reaction product according to claim 51, wherein (b) is selected from the groups 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.

53. The oil soluble reaction product according to claim 49, wherein (b) is a mixture of poly(ethyleneamines) averaging about 5 to about 7 nitrogen atoms per molecule.

54. An oleaginous composition comprising an oleaginous lubricating oil and an oil soluble dispersant comprising the oil soluble reaction product of a reaction mixture comprising:

(a) at least one aminated hydrocarbyl substituted C₄ to C₁₀ monounsaturated dicarboxylic acid producing material formed by first reacting an olefin polymer of C₂ to C₁₀ monoolefin having a molecular weight of about 700 to 5,000 with a C₄ to C₁₀ monounsaturated dicarboxylic acid material, wherein there are 0.7 to 2.0 dicarboxylic acid producing moieties per molecule of said olefin polymer used in the reaction, and then with a non-heterocyclic polyamine; and

(b) at least one non-polymerizable lactone selected from the group consisting of lactones and thiolactones having up to four carbon atoms in the lactone ring; and

(c) at least one polymerizable C₅ -C₉ lactone, wherein there are 0.2-100 molar proportions of reactant (c) per molar proportion of reactant (a) in said reaction product, wherein said reactant (a) is first reacted with reactant (b), and wherein the intermediate reaction product of reactants (a) and (b) is used to initiate ring opening polymerization of said reactant (c) at a temperature of from about 30°

to about 200°

C.

55. The oleaginous composition according to claim 54, wherein said reactant (b) is butyrolactone, wherein reactant (c) is E-caprolactone and wherein said reaction product of reactants (a), (b) and (c) contains the unit ##STR19## where m is 0.5 to 20.

56. The oleaginous composition according to claim 54, wherein said polyamine is an aliphatic saturated amine having the general formula ##STR20## 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 and R'"'"' is H such that there are at least two primary or secondary amino groups present in said polyamine.

57. The oleaginous composition according to claim 54, wherein said polyamine is a mixture of poly(ethyleneamines) averaging about 5 to about 7 nitrogen atoms per molecule.

58. A lubricating oil composition comprising lubricating oil and oil soluble reaction product useful as an oil additive, said reaction product being the product of reaction of:

(a) polymer of C₂ to C₁₀ monoolefin of 700 to 5,000 molecular weight 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, and

(b) non-heterocyclic polyamine containing 2 to 60 carbon atoms and 2 to 12 nitrogen groups, further reacted with

(c) non-polymerizable lactone selected from the group consisting of lactones and thiolactones having up to four carbon atoms in the lactone ring, and still further reacted with

(d) polymerizable C₅ -C₉ lactone,

wherein there are 0.2 to 100 molar proportions of polymerizable lactone per molar proportion of the product obtained by the reaction of (a) with (b) in said oil soluble reaction product, and wherein (a) if first reacted with (b) to form an intermediate product which is then reacted with (c) to form a second intermediate product which is then reacted with (d) at a temperature of from about 30°

to about 200°

for a period sufficient to effect ring opening polymerization of said C₅ -C₉ lactone.

59. The lubricating oil composition according to claim 58, wherein (c) is butyrolactone, wherein (d) is caprolactone, and wherein there are 0.5 to 20 molar proportions of caprolactone per molar proportion of product obtained by the reaction of (a) with (b) in said oil soluble reaction product.

60. The lubricating oil composition according to claim 59, wherein said amine is an aliphatic saturated amine having the general 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 and R'"'"' is H such that there are at least two primary or secondary amino groups present in said amine.

61. The lubricating oil composition according to claim 59, wherein said amine is a mixture of poly(ethyleneamines) averaging about 5 to about 7 nitrogen atoms per molecule.

62. The lubricating oil composition according to claim 58, wherein (a) is polyisobutylene of about 700 to 3,000 molecular weight substituted with succinic anhydride moieties.

63. The lubricating oil composition according to claim 60, wherein (a) is polyisobutylene of about 700 to 3,000 molecular weight substituted with succinic anhydride moieties.

64. 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 dispersant formed by reacting a polyolefin substituted with polyamine, then with a non-polymerizable lactone selected from the group consisting of lactones and thiolactones having up to four carbon atoms in the lactone ring, and then with a polymerizable C₅ -C₉ lactone at a temperature of from about 30°

to about 200°

for a period sufficient to effect ring opening polymerization of said C₅ -C₉ lactone, wherein said substituted succinic acid or anhydride has about 0.7 to 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 molecular weight of about 700 to 5,000, and wherein said dispersant has about 0.2 to 100 molar proportions of polymerizable lactone moieties per molar proportion of polyolefin; and

an effective amount of a viscosity modifier.

65. The composition according to claim 64, wherein said dispersant is the reaction product of polyisobutene reacted with maleic anhydride, then with a polyamine, and then with butyrolactone.

66. The composition according to claim 65, wherein said composition also contains an effective amount of an anti-wear agent.

67. An additive concentrate comprising about 20 to 80 wt. % lubricating oil and about 20 to 80 wt. % of a dispersant which is a lactone modified adduct formed by reacting at a temperature of from about 30°

to about 200°

C., on the average, 0.2 to 100 molar proportions of (I) polymerizable C₅ -C₉ lactone per molar proportion of (II) nonpolymerizable lactone modified, amine neutralized, hydrocarbyl substituted, C₄ to C₁₀ monounsaturated dicarboxylic acid producing material which, in turn, has been formed by first reacting (a) non-heterocyclic polyamine with the reaction product of (b) olefin polymer of C₂ to C₁₀ monoolefin having a molecular weight of about 700 to 5,000 and (c) C₄ to C₁₀ monounsaturated dicarboxylic acid material, wherein there are an average of 0.7 to 2.0 dicarboxylic acid producing moieties per molecule of said olefin polymer used in the reaction, and then reacting the resulting reaction product with (d) non-polymerizable lactone, said nonpolymerizable lactone being selected from the group consisting of lactones and thiolactones having up to four carbon atoms in the lactone ring.

68. The concentrate according to claim 67, wherein (b) is polyisobutylene, (c) is maleic anhydride, (d) is butyrolactone, and (I) is caprolactone, and wherein said dispersant is formed by reacting said polyisobutylene with said maleic anhydride, then reacting the polyisobutylene-maleic anhydride reaction product with said polyamine, then with said butyrolactone, and then with said caprolactone.

69. The concentrate according to claim 68, which also contains an effective amount of a viscosity modifier.

70. The concentrate according to claim 69, which also contains an effective amount of an antiwear agent.

71. An additive concentrate comprising about 20 to 80 wt. % lubricating oil and about 20 to 80 wt. % of an oil soluble caprolactone adduct of a hydrocarbyl substituted C₄ to C₁₀ monounsaturated dicarboxylic acid producing material which has been reacted with a non-heterocyclic polyamine and with a non-polymerizable lactone selected from the group consisting of lactones and thiolactones having up to four carbon atoms in the lactone ring prior to being reacted with caprolactone at a temperature of about 30°

to about 200°

C. for a period of time sufficient to effect ring opening polymerization of said caprolactone, said adduct being useful as an improved dispersant, said hydrocarbyl substituted material being formed by reacting an olefin polymer of a C₂ to C₁₀ monoolefin having a molecular weight of about 700 to 5,000 and a C₄ to C₁₀ saturated dicarboxylic acid or anhydride, wherein there are 0.7 to 2.0 dicarboxylic acid producing moieties per molecule of said olefin polymer used in the reaction, and said adduct containing, on the average, from 0.5 to 20 caprolactone moieties per molecule of said olefin polymer present in said adduct.

72. An additive concentrate according to claim 71, wherein said C₄ to C₁₀ acid producing material is polyisobutylene substituted with 0.7 to 2.0 moles of succinic anhydride units per mole of polyisobutylene.

73. An additive concentrate according to claim 72, which also contains an effective amount of a viscosity modifier.

74. An additive concentrate according to claim 73, which also contains an anti-wear effective amount of a zinc dihydrocarbyl dithiophosphate.