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EP0336664A2
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Improved dispersant additives derived from amido-amine adducts
Assignee: ExxonMobil Chemical Patents Inc
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Filing: 1989-03-31
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Granted: —
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Expires: 2009-03-31
Abstract
Abstract The present invention is directed to a lactone modified dispersant additive comprising at least one adduct of (A) a polyolefin of 300 to 10,000 number average molecular weight substituted with at least 0.3 (e.g., from about 1 to 4) dicarboxylic acid producing moieties (preferably acid or anhydride moieties) per polyolefin molecule, (B) an amido-amine or thioamido-amine characterized by being a reaction product of at least a polyamine and an alpha, beta-unsaturated compound of the formula: <CHEM> wherein X is sulfur or oxygen, Y is -OR<4>, -SR<4>, or -NR<4>(R<5>), and R<1>, R<2>, R<3>, R<4> and R<5> are the same or different and are hydrogen or substituted or unsubstituted hydrocarbyl, and a C5 - C9 lactone material.
Inventors
- 👤 Antonio Gutierrez
- 👤 Robert Dean Lundberg
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-04 16:53
CPC Classifications
C; C10; C10M; C10M159/00; C10M159/12; C08; C08F; C08F8/00; C08F8/14; C08F8/34; C08G; C08G63/00; C08G63/91; C08G63/912; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/18; C10L1/1817; C10L1/22; C10L1/221; C10L1/24; C10L1/2493; C10M129/00; C10M129/02; C10M129/16; C10M129/20; C10M129/86; C10M129/95; C10M133/00; C10M133/52; C10M149/00; C10M149/12; C10M149/14; C10M149/22; C10M151/00; C10M151/04; C10M2205/00; C10M2205/02; C10M2205/026; C10M2205/06; C10M2207/00; C10M2207/02; C10M2207/023; C10M2207/027; C10M2207/028; C10M2207/04; C10M2207/044; C10M2207/10; C10M2207/14; C10M2207/144; C10M2207/146; C10M2207/16; C10M2207/26; C10M2207/262; C10M2207/28; C10M2207/287; C10M2207/289; C10M2209/00; C10M2209/02; C10M2209/08; C10M2209/084; C10M2209/086; C10M2209/10; C10M2209/101; C10M2209/103; C10M2209/104; C10M2209/107; C10M2215/00; C10M2215/02; C10M2215/04; C10M2215/042; C10M2215/06; C10M2215/064; C10M2215/065; C10M2215/086; C10M2215/22; C10M2215/221; C10M2215/225; C10M2215/226; C10M2215/24; C10M2215/26; C10M2215/28; C10M2215/30; C10M2217/00; C10M2217/02; C10M2217/028; C10M2217/04; C10M2217/046; C10M2217/06; C10M2219/00; C10M2219/04; C10M2219/044; C10M2219/046; C10M2219/06; C10M2219/062; C10M2219/066; C10M2219/08; C10M2219/082; C10M2219/085; C10M2219/087; C10M2219/088; C10M2219/089; C10M2219/10; C10M2219/102; C10M2219/104; C10M2219/106; C10M2221/00; C10M2221/02; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/042; C10M2223/045; C10M2223/12; C10M2225/00; C10M2225/04; C10M2225/041; C10M2227/00; C10M2227/09; C10M2229/00; C10M2229/04; C10M2229/041; C10N; C10N2010/00; C10N2010/02; C10N2010/04; C10N2010/12; C10N2040/00; C10N2040/04; C10N2040/042; C10N2040/044; C10N2040/046; C10N2040/06; C10N2040/25; C10N2040/252; C10N2040/253; C10N2040/255; C10N2040/26; C10N2070/00; C10N2070/02
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
221 words
A poly (C s to Cg) adduct of an aminated hydrocarbyl substituted dicarboxylic acid producing material useful as an oil additive and formed by reacting : (A) a long chain hydrocarbyl substituted C 4 to C 10 monounsaturated dicarboxylic acid producing material formed by reacting an olefin polymer of C 2 to C 10 monoolefin having a number average molecular weight of 300 to 10,000 and a C 4 to C 10 monounsaturated acid material, said acid producing material having an average of at least 0.8 dicarboxylic acid producing moieties, per molecule of said olefin polymer present in the reaction mixture used to form said acid producing material; (B) an amido-amine or a thioamido-amine characterized by being a reaction product of at least a polyamine and an alpha, beta-unsaturated compound of the formula: wherein X is sulphur or oxygen, Y is -OR 4 , -SR 4 , or -NR 4 (R 5 ), and R 1 , R 2 , R 3 , R4and R 5 are the same or different and are hydrogen or substituted or unsubstituted hydrocarbyl; and (C) a C 5 to C s lactone material, said poly (Cs to Cs) adduct containing the unit -[C(O)(CH 2 ) 2 O]- m wherein m has an average value of from 0.2 to 100 and z is 4 to 8.
Claim 2
Dependent Claim
221 words
A poly (C s to Cg) adduct of an aminated hydrocarbyl substituted dicarboxylic acid producing material useful as an oil additive and formed by reacting : (A) a long chain hydrocarbyl substituted C 4 to C 10 monounsaturated dicarboxylic acid producing material formed by reacting an olefin polymer of C 2 to C 10 monoolefin having a number average molecular weight of 300 to 10,000 and a C 4 to C 10 monounsaturated acid material, said acid producing material having an average of at least 0.8 dicarboxylic acid producing moieties, per molecule of said olefin polymer present in the reaction mixture used to form said acid producing material; (B) an amido-amine or a thioamido-amine characterized by being a reaction product of at least a polyamine and an alpha, beta-unsaturated compound of the formula: wherein X is sulphur or oxygen, Y is -OR 4 , -SR 4 , or -NR 4 (R 5 ), and R 1 , R 2 , R 3 , R4and R 5 are the same or different and are hydrogen or substituted or unsubstituted hydrocarbyl; and (C) a C 5 to C s lactone material, said poly (Cs to Cs) adduct containing the unit -[C(O)(CH 2 ) 2 O]- m wherein m has an average value of from 0.2 to 100 and z is 4 to 8.
Claim 3
Dependent Claim
25 words
The poly (C s - Cg) adduct according to claim 1, wherein reactants (A) and (B) are first contacted, followed by addition of reactant (C).
Claim 4
Dependent Claim
27 words
The poly (C s - C 9 ) adduct according to claim 1, wherein reactants (B) and (C) are first contacted, followed by addition of reactant (A).
Claim 5
Dependent Claim
37 words
The poly (Cs - C g ) adduct according to any of claims 1 to 3, wherein said polyamine comprises amines containing from 2 to 60 carbon atoms and from 3 to 12 nitrogen atoms per molecule.
Claim 6
Dependent Claim
41 words
The poly (Cs - C g ) adduct according to claim 4, wherein said amine comprises a polyalkylene-polyamine wherein said alkylene groups contain 2 to 40 carbons and said polyalkylene polyamine contains from 5 to about 9 nitrogen atoms per molecule.
Claim 7
Dependent Claim
97 words
The poly (C s - C s ) adduct according to claim 1, wherein said hydrocarbyl substituted C 4 to C 10 monounsaturated dicarboxylic acid producing material comprises polyisobutylene of from 900 to 5000 number average molecular weight substituted with succinic anhydride moieties, said polyamine comprises polyalkylene-polyamine wherein said alkylene groups contain 2 to 6 carbons and said polyalkylene polyamine contains 5 to 9 nitrogen atoms per molecule, and said alpha, beta-unsaturated compound comprises at least one member selected from methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, methyl methacrylate, ethyl methacrylate, propyl methacrylate, and butyl methacrylate.
Claim 8
Dependent Claim
39 words
The poly (C s - C 9 ) adduct according to any of claims 1 to 6, wherein said olefin polymer comprises polyisobutylene, and wherein said number average molecular weight of said olefin polymer is from 1300 to 4,000.
Claim 9
Dependent Claim
21 words
The poly (Cs - Cs) adduct of any of claims 1 to 7, wherein said monounsaturated acid material comprises maleic anhydride.
Claim 10
Dependent Claim
39 words
The poly (C s - Cg) adduct according to any of claims 1 to 8 wherein about 1 to 5 moles of said acid producing material per primary nitrogen equivalent of said amido-amine are present in said reaction mixture.
Claim 11
Dependent Claim
30 words
The poly (Cs - C s ) adduct according to claim 9 wherein said amido-amine contains an average of from 1 to 3 amido groups per molecule of said amido-amine.
Claim 12
Dependent Claim
28 words
The poly (C s - C 9 ) adduct according to any of claims 1 to 10 wherein said C s to C 9 lactone material is E-caprolactone.
Claim 13
Dependent Claim
277 words
A process for producing a poly (C s - C 9 ) adduct useful as an oil additive which comprises: (a) providing a hydrocarbyl substituted C 4 to C 10 monoolefin having a number average molecular weight of 700 to 10,000 and a C 4 . to C 10 monounsaturated acid material, said acid producing material having an average of at least 0.8 dicarboxylic acid producing moieties, per molecule of said olefin polymer present in the reaction mixture used to form said acid producing material; (b) providing an amido-amine compound having at least one primary amino group prepared by reacting at least one polyamine with at least one alpha, beta-unsaturated compound of the formula: wherein X is sulphur or oxygen, Y is -OR 4 , -SR 4 , or -NR 4 (R 5 ), and R 1 , R 2 , R 3 , R 4 and R 5 are the same or different and are hydrogen or substituted or unsubstituted hydrocarbyl; (c) contacting the said acid producing material with said amido-amine compound under conditions sufficient to effect reaction of at least a portion of the primary amino groups on said amido-amine compound with at least a portion of the acid-producing groups in said acid producing material, to form a first adduct; and (d) contacting said first adduct with a C 5 to C 9 lactone material under conditions sufficient to ring open the lactone ring of said lactone material to form said poly (C s - C g ) adduct containing the unit -[C(O)-(CH 2 ) 2 O]- m wherein m has an average value of from 0.2 to 100 and z is 4 to 8.
Claim 14
Dependent Claim
277 words
A process for producing a poly (C s - C 9 ) adduct useful as an oil additive which comprises: (a) providing a hydrocarbyl substituted C 4 to C 10 monoolefin having a number average molecular weight of 700 to 10,000 and a C 4 . to C 10 monounsaturated acid material, said acid producing material having an average of at least 0.8 dicarboxylic acid producing moieties, per molecule of said olefin polymer present in the reaction mixture used to form said acid producing material; (b) providing an amido-amine compound having at least one primary amino group prepared by reacting at least one polyamine with at least one alpha, beta-unsaturated compound of the formula: wherein X is sulphur or oxygen, Y is -OR 4 , -SR 4 , or -NR 4 (R 5 ), and R 1 , R 2 , R 3 , R 4 and R 5 are the same or different and are hydrogen or substituted or unsubstituted hydrocarbyl; (c) contacting the said acid producing material with said amido-amine compound under conditions sufficient to effect reaction of at least a portion of the primary amino groups on said amido-amine compound with at least a portion of the acid-producing groups in said acid producing material, to form a first adduct; and (d) contacting said first adduct with a C 5 to C 9 lactone material under conditions sufficient to ring open the lactone ring of said lactone material to form said poly (C s - C g ) adduct containing the unit -[C(O)-(CH 2 ) 2 O]- m wherein m has an average value of from 0.2 to 100 and z is 4 to 8.
Claim 15
Dependent Claim
36 words
The process according to claim 12, wherein said amine comprises a polyalkylene polyamine wherein said alkylene group contain 2 to 40 carbons and said polyalkylene polyamine contains from 5 to about 9 nitrogen atoms per molecule.
Claim 16
Dependent Claim
94 words
The process according to claim 13, wherein said hydrocarbyl substituted C 4 to C 10 monounsaturated dicarboxylic acid producing material comprises polyisobutylene of from 900 to 5000 number average molecular weight substituted with succinic anhydride moieties, said amine comprises polyalkylene polyamine wherein said alkylene groups contain 2 to 6 carbons and said polyalkylene polyamine contains 5 to 9 nitrogen atoms per molecule, and said acrylate-type compound comprises at least one member selected from the group consisting of methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, methyl methacrylate, ethyl methacrylate, propyl methacrylate, and butyl methacrylate.
Claim 17
Dependent Claim
33 words
The process according to any of claims 12 to 14, wherein said olefin polymer comprises polyisobutylene, and wherein said number average molecular weight of said first olefin polymer is from 1300 to 4,000.
Claim 18
Dependent Claim
25 words
A concentrate containing from about 3 to 45 wt. % of the poly (C s - Cg) adduct of any of claims 1 to 11.
Claim 19
Dependent Claim
25 words
A concentrate as described in claim 16 containing from 10 to 35 wt. % of the poly (C s - Cg) adduct of claim 4.
Claim 20
Dependent Claim
30 words
A lubricating oil composition containing from 0.1 to 20 wt. % of the poly (C s - C g ) adduct prepared according to any of claims 1 to 11.
References Cited (Backward Citations)
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