Lactone modified mono-or dicarboxylic acid based adduct dispersant compositions

• US 4,906,394 A
• Filed: 10/07/1986
• Issued: 03/06/1990
• 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): Howard, Jacqueline V.
• Assistant Examiner(s): Medley, Margaret B.
• Application Number:
  US06/916,108
• Time in Patent Office: 1,246 Days
• Field of Search: 252/51.5 A, 44/66, 44/73, 260/404.5, 521/140, 525/186, 525/190, 560/1, 560/155, 564/134, 564/141, 549/263
• US Class Current: 508/222
• CPC Class Codes: C07D 263/14 with radicals substituted by oxygen atoms
• CPC Class Codes: C07D 315/00 Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
• 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 63/91 Polymers modified by chemical after-treatment
• CPC Class Codes: C10L 1/221 compounds of uncertain formula; reaction products where mixtures of compounds are obtained
• CPC Class Codes: C10M 129/76 containing free hydroxy or carboxyl groups
• CPC Class Codes: C10M 129/95 Esters
• CPC Class Codes: C10M 133/16 Amides; Imides
• CPC Class Codes: C10M 133/48 the ring containing both nitrogen and oxygen
• 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 2207/289 containing free hydroxy groups
• 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 2215/26 Amines
• 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 2227/09 Complexes with metals
• CPC Class Codes: C10N 2040/00 Specified use or application for which the lubricating composition is intended
• CPC Class Codes: C10N 2040/02 Bearings
• 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 2040/08 : Hydraulic fluids, e.g. brake-fluids
• CPC Class Codes: C10N 2040/20 : Metal working
• CPC Class Codes: C10N 2040/25 : Internal-combustion engines
• CPC Class Codes: C10N 2040/251 : Alcohol fueled engines
• CPC Class Codes: C10N 2040/255 : Gasoline engines
• CPC Class Codes: C10N 2040/28 : Rotary engines
• CPC Class Codes: C10N 2040/30 : Refrigerators lubricants or compressors lubricants
• CPC Class Codes: C10N 2040/32 : Wires, ropes or cables lubricants
• CPC Class Codes: C10N 2040/34 : Lubricating-sealants
• CPC Class Codes: C10N 2040/36 : Release agents or mold release agents
• CPC Class Codes: C10N 2040/38 : Conveyors or chain belts
• CPC Class Codes: C10N 2040/40 : Generators or electric motors in oil or gas winning field
• CPC Class Codes: C10N 2040/42 : Flashing oils or marking oils
• CPC Class Codes: C10N 2040/44 : Super vacuum or supercritical use
• CPC Class Codes: C10N 2040/50 : Medical uses
• 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 an aliphatic hydrocarbyl saturated or unsaturated, straight chain or branched chain monocarboxylic or dicarboxylic acylating agent having from about one to about 165 total carbon atoms in said straight or branched chain to insure that the resulting lactone adduct is hydrocarbon soluble. 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 formed by reacting an aliphatic hydrocarbyl saturated or unsaturated, natural or synthetic, straight chain or branched chain monocarboxylic or dicarboxylic acylating agent heaving from about 1 to about 165 total carbon atoms with the reaction product 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 amino alcohol containing up to about 50 total carbon atoms, from 1 to about 5 nitrogen atoms and from 1 to about 15 hydroxyl groups, and (c) mixtures of (a) and (b), said aliphatic acylating agent having at least about twelve carbon atoms in said straight or branched chain to produce lactone adduct material that is hydrocarbon soluble.

2. The C₅ -C₉ lactone adduct material of claim 1, wherein said acylating agent is a member selected from the group of long chain fatty acids or dimers thereof and hydrocarbyl substituted C₄ -C₁₀ monounsaturated dicarboxylic acid materials, wherein said hydrocarbyl group contains from about twelve to about eighteen carbon atoms.

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 acylating agent is selected from the group consisting of isostearic acid, stearic acid, linoleic acid, oleic acid, dimers of said acids and octadecenyl succinic anhydride.

5. 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.

6. The C₅ -C₉ lactone adduct material of claim 5, 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.

7. 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.

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

9. The C₅ -C₉ lactone adduct material of claim 1, 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

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 subtituents on the R group is represented by the value of "a", which is a number from 3 to 6.

10. The C₅ -C₉ lactone adduct material of claim 4, 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 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 C₅ -C₉ lactone 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 C₅ -C₉ lactone adduct material of claim 4, wherein said polyamine is selected from the group consisting 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.

13. The C₅ -C₉ lactone adduct material of claim 4, wherein said polyamine is a mixture of poly (ethyleneamines) averaging about 5 to about 7 nitrogen atoms per molecule.

14. The C₅ -C₉ lactone adduct material of claim 4, 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

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.

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

16. The C₅ -C₉ lactone adduct material of claim 15, 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.

17. The C₅ -C₉ lactone adduct mateial of claim 16, wherein said amino alcohol is tris (hydroxymethyl) amino methane.

18. The C₅ -C₉ lactone adduct material of claim 4, wherein said C₅ -C₉ lactone is reacted with an amino alcohol.

19. The C₅ -C₉ lactone adduct material of claim 18, 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.

20. The C₅ -C₉ lactone adduct material of claim 19, wherein said amino alcohol is tris (hydroxymethyl) amino methane.

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

48. 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.

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 4.

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 16.

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 5.

52. A lubricating oil comprising a major amount of lubricating oil about 0.1 to 10 wt % of the C₅ -C₉ lactone adduct material of claim 8.

21. A process for preparing a C₅ -C₉ lactone adduct material useful as an oil additive, which comprises the steps of:

(i) reacting a C₅ -C₉ lactone with a member selected from the group consisting of (a) polyamines having from about 2 to about 60 total carbon atoms and from about 2 to about 12 nitrogen atoms, (b) amino alcohols containing up to about 50 total carbon atoms, from 1 to about 5 nitrogen atoms, and from 1 to about 15 hydroxyl groups, and (c) mixtures of (a) and (b) to form a lactone adduct intermediate product; and

(ii) reacting said intermediate product with an aliphatic hydrocarbyl saturated or unsaturated, natural or synthetic, straight chain or branched chain monocarboxylic or dicarboxylic acylating agent having from about twelve to about eighteen total carbon atoms and at least twelve carbon atoms in the hydrocarbyl group.

22. The process of claim 21, wherein said acylating agent is a member selected from the group of long chain fatty acids or dimers thereof and hydrocarbyl substituted C₄ -C₁₀ monounsaturated dicarboxylic acid materials, wherein said hydrocarbyl group contains from about twelve to about eighteen carbon atoms.

23. The process of claim 22, 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.

24. The process of claim 22, wherein said lactone is E-caprolactone.

25. The process of claim 24, wherein said acylating agent is selected from the group consisting of isostearic acid, stearic acid, linoleic acid, oleic acid, dimers of said acids and octadecenyl succinic anhydride.

26. The process of claim 24, wherein said C₅ -C₉ lactone is reacted with a polyamine, and wherein said polyamine is an aliphatic saturated amine having the 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'"'"' must be H such that there are at least two of either primary or secondary amino groups.

27. The process of claim 26, 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;

di-(1,3-propylene) triamine;

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

N dodecyl-1,3-propane diamine.

28. The process of claim 21, wherein said polyamine is selected from the group consisting alicyclic diamines, imidazolines, morpholines, and N-aminoalkyl piperazines of the general formula:

##STR19## 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.

29. The process of claim 21, wherein said polyamine is a mixture of poly (ethyleneamines) averaging about 5 to about 7 nitrogen atoms per molecule.

30. The process of claim 21, 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

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.

31. The process of claim 21, wherein said C₅ -C₉ lactone is reacted with an amino alcohol.

32. The process of claim 31, wherein said amino alcohol is a 2,2-disubstituted-2-amino-1-alkanol of the formula ##STR20## 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.

33. The process of claim 32, wherein said amino alcohol tris (hydroxymethyl) amino methane.

34. An oleaginous composition comprising (I) a lubricating oil and (II) a C₅ -C₉ lactone adduct material, said adduct material being prepared by 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 amino alcohol containing up to about 50 total carbon atoms, from 1 to about five nitrogen atoms and from 1 to about 15 hydroxyl groups, and (c) mixtures of (a) and (b) to form an intermediate lactone adduct, and then reacting said intermediate lactone adduct with (iii) an aliphatic hydrocarbyl saturated or unsaturated, natural or synthetic, straight chain or branched chain monocarboxylic or dicarboxylic acylating agent having from about 12 to about 165 total carbon atoms and at least about twelve carbon atoms in said straight or branched chain to insure that the resulting lactone adduct material is hydrocarbon soluble.

35. The oleaginous composition of claim 34, wherein said acylating agent is a member selected from the group of long chain fatty acids or dimers thereof and hydrocarbyl substituted C₄ -C₁₀ monounsaturated dicarboxylic acid materials, wherein said hydrocarbyl group contains from about twelve to about eighteen carbon atoms.

36. The oleaginous composition of claim 35, wherein said lactone is E-caprolactone.

37. The oleaginous composition of claim 36, where said acylating agent is selected from the group consisting of isostearic acid, stearic acid, linoleic acid, oleic acid, dimers of said acids and octadecenyl succinic anhydride.

38. The oleaginous composition of claim 34, wherein said C₅ -C₉ lactone is reacted with a polyamine, and wherein said polyamine 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.

39. The oleaginous composition of claim 34, 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.

40. The oleaginous composition of claim 34, wherein said polyamine is selected from the group consisting of alicyclic diamines, imidazolines, morpholines and N-aminoalkyl piperazines of the general formula:

##STR22## 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.

41. The oleaginous composition of claim 34, wherein said polyamine is a mixture of poly (ethyleneamines) averaging about 5 to about 7 nitrogen atoms per molecule.

42. The oleaginous composition of claim 34, 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

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.

43. The oleaginous composition of claim 46, wherein said C₅ -C₉ lactone is reacted with an amino alcohol.

44. The oleaginous composition of claim 43, wherein said amino alcohol is a 2,2-disubstituted-2-amino-1-alkanol of the formula ##STR23## 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.

45. The oleaginous composition of claim 44, wherein said amino alcohol is tris (hydroxymethyl) amino methane.

46. The oleaginous composition of claim 34, wherein said oleaginous material is lubricating oil.

53. An oil soluble dispersant useful as an oil additive, comprising the product of a reaction mixture comprising:

(I) an aliphatic hydrocarbyl saturated or unsaturated, natural or synthetic, straight chain or branched chain monocarboxylic or dicarboxylic acylating agent having from about 1 to about 165 total carbon atoms; 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 amino alcohol containing up to about 50 total carbon atoms, from 1 to about five nitrogen atoms and from 1 to about 15 hydroxyl groups, or mixtures of (i) and (ii),

wherein there are from 1 to about 10 C₅ -C₉ lactone derived moieties per unit of said adduct (II) used in the reaction.

54. An oil soluble dispersant according to claim 53, wherein said C₅ -C₉ lactone is caprolactone.

55. An oil soluble dispersant according to claim 54, wherein said caprolactone is reacted with a polyamine.

56. An oil soluble despersant according to claim 55, wherein said polyamine is an aliphatic saturated amine having the general formula ##STR24## 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.

57. An oil soluble dispersant according to claim 56, 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.

58. The oil soluble dispersant of claim 55, wherein said polyamine is selected from the group consisting of alicyclic diamines, imidazoles, morpholines, and N-aminoalkyl piperazines of the general formula:

##STR25## 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.

59. The oil soluble dispersant of claim 55, wherein said polyamine is a mixture of poly(ethyleneamines) averaging about 5 to about 7 nitrogen atoms per molecule.

60. An oil soluble dispersant according to claim 55, 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 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.

61. An oil soluble dispersant according to claim 54, wherein said caprolactone is reacted with an amino alcohol.

62. An oil soluble dispersant according to claim 61, wherein said amino alcohol is a 2,2-disubstituted-2-amino-1-alkanol of the formula ##STR26## 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.

63. An oil soluble dispersant according to claim 62, wherein said amino alcohol is tris(hydroxymethyl)amino methane.

64. An oil soluble reaction product useful as an oil additive of:

(a) an aliphatic hydrocarbyl saturated or unsaturated, natural or synthetic, straight chain or branched chain monocarboxylic or dicarboxylic acylating agent having from about to about 18 total carbon atoms

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

(c) C₅ -C₉ lactone, wherein (b) is first reacted with (c) and the resulting product is then reacted with (a), and wherein there are about 0.2 to 100 molar proportions of (c) per molar proportion of said reaction product.

65. An oil soluble reaction product according to claim 64 wherein 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.

66. An oil soluble reaction product useful as an oil additive of:

(a) an aliphatic hydrocarbyl saturated or unsaturated, natural or synthetic, straight chain or branched chain monocarboxylic or dicarboxylic acylating agent having from about 12 to about 18 total carbon atoms

(b) amino alcohol containing up to about 50 total carbon atoms, from 1 to about 5 nitrogen atoms and from 1 to about 15 hydroxyl groups, and

(c) C₅ -C₉ lactone,

wherein (b) is first reacted with (c) and the resulting product is then reacted with (a), and wherein there are about 0.2 to 100 molar proportions of (c) per molar proportion of said reaction product.

67. An oil soluble reaction product according to claim 66 wherein (c) is E-caprolactone, and wherein there are about 1 to 5 molar proporations of (c) per molar proportion of said reaction product.

68. A lubricating oil composition comprising lubricating oil and an oil soluble reaction product useful as an oil additive, said reaction product being the product of reaction of the intermediate product formed 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 about 2 to about 12 nitrogen atoms an amino alcohol containing up to about 50 total carbon atoms, from 1 to about five nitrogen atoms and from 1 to about 15 hydroxyl groups, wherein there are 0.2 to 100 molar proportions of (b) in said intermediate product, further reacted with (c) an aliphatic hydrocarbyl saturated or unsaturated, natural or synthetic, straight chain or branched chain monocarboxylic or dicarboxylic acylating agent having from about 12 to about 18 total carbon atoms.

69. A lubricating oil composition according to claim 68, wherein (a) is caprolactone, and wherein there are from about one to about five molar proportions of caprolactone per molar proportion of product obtained by the reaction of (a) with (b).

70. 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 an aliphatic hydrocarbyl saturated or unsaturated, natural or synthetic, straight chain or branched chain monocarboxylic or dicarboxylic acylating agent having from about 12 to about 18 total carbon atoms with the reaction product of a C₅ -C₉ lactone and at least one member selected from the group consisting of (a) polyamines having from about 2 to 60 total carbon atoms and from about 2 to about 12 nitrogen atoms, and (b) amino alcohols containing up to about 50 total carbon atoms, from 1 to about five nitrogen atoms and from 1 to about 15 hydroxyl groups, wherein said dispersant has about one to five molar proportion of acylating agent moieties; and

about 3 to 25 wt. % of a metal containing detergent additive.

71. A composition according to claim 70, wherein said C₅ -C₉ lactone is caprolactone.

72. A composition according to claim 71, wherein said composition also contains an effective amount of a zinc dihydrocarbyl dithiophosphate.

73. An additive concentrate comprising about 20 to 90 wt. % lubricating oil and 20 to 80 wt. % of a dispersant which is a C₅ -C₉ lactone adduct material formed by first reacting about 0.2 to 100 molar proportions of a C₅ -C₉ lactone per molar proportion of at least one member selected from the group consisting of (a) polyamines having from about 2 to 60 total carbon atoms and from about 2 to about 12 nitrogen atoms and (b) amino alcohols containing up to about 50 total carbon atoms, from 1 to about five nitrogen atoms and from 1 to about 15 hydroxyl groups, to from a lactone adduct intermediate, and then reacting said intermediate with an aliphatic hydrocarbyl saturated or unsaturated, natural or synthetic, straight chain or branched chain monocarboxylic or dicarboxylic acylating agent having from about 12 to about 18 total carbon atoms.

74. A concentrate according to claim 73, wherein said C₅ -C₉ lactone is caprolactone and which also contains an effective amount of a viscosity modifier.

75. A concentrate according to claim 74, which also contains an effective amount of a zinc dihydrocarbyl dithiophosphate.

76. An additive concentrate comprising about 20 to 80 wt. % lubricating oil and about 20 to 80 wt. % of an oil soluble reaction product of a caprolactone adduct and an acylating agent selected from the group consisting of long chain fatty acids, long chain fatty acid dimers and hydrocarbyl substituted C₄ to C₁₀ monounsaturated dicarboxylic acid producing material having from about twelve to about 18 carbon atoms in said hydrocarbyl substituent, said caprolactone adduct being prepared by reacting caprolactone with at least one member selected from the group consisting of (a) polyamines having from about 2 to 60 total carbon atoms and from about 2 to about 12 nitrogen atoms and (b) amino alcohols containing up to about 50 total carbon atoms, from 1 to about five nitrogen atoms and from 1 to about 15 hydroxyl groups.

77. An additive concentrate according to claim 76, wherein said hydrocarbyl substituted C₄ to C₁₀ acid producing material is octadecenyl succinic anhydride.

78. An additive concentrate according to claim 76, wherein said long chain fatty acids and said long chain fatty acid dimers are selected from the group consisting of isostearic acid, stearic acid, linoleic acid, oleic acid and dimers thereof.