Patent EP0113582A2 successfully refreshed from Google Patents.
EP0113582A2
Expired / Lapsed
EP
⏱️ 0.0 years remaining
Macrocyclic polyamine and polycyclic polyamine multifunctional lubricating oil additives
Assignee: ExxonMobil Technology and Engineering Co
•
Filing: 1983-12-22
•
Granted: —
•
Expires: 2003-12-22
Abstract
Abstract There are disclosed macrocyclic and polycyclic polyamine lubricating oil additives formed by cyclodehydration of reaction products of hydrocarbon substituted succinic anhydrides or carboxylic acids with poly 3-amino propyl compounds or by acylation of macrocyclic polyamines and polycyclic polyamines with hydrocarbon substituted succinic anhydride or carboxylic acids. These compounds are useful as dispersants and dispersants-V.I. improvers in both gasoline and diesel engine lubricating oil compositions and are also useful fuel additives.
Inventors
- 👤 Stanley James Brois
- 👤 Antonio Gutierrez
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-04 16:43
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04; C08; C08F; C08F8/00; C08F8/30; C08F8/32; C10; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/22; C10L1/232; C10M; C10M133/00; C10M133/02; C10M133/38; C10M133/52; C10M133/58; C08F2800/00; C08F2800/20; C10M2205/00; C10M2205/02; C10M2205/026; C10M2205/06; C10M2205/22; C10M2207/00; C10M2207/02; C10M2207/023; C10M2207/026; C10M2207/027; C10M2207/028; 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; C10M2215/00; C10M2215/02; C10M2215/04; C10M2215/22; C10M2215/221; C10M2215/225; C10M2215/226; C10M2215/24; C10M2215/26; C10M2215/30; C10M2217/00; C10M2217/04; C10M2217/046; C10M2217/06; C10M2219/00; C10M2219/02; C10M2219/022; C10M2219/024; C10M2219/04; C10M2219/044; C10M2219/046; C10M2219/08; C10M2219/082; C10M2219/087; C10M2219/088; C10M2219/089; C10M2219/10; C10M2219/102; C10M2219/104; C10M2219/106; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/045; C10M2223/12; C10M2225/00; C10M2225/04; C10M2225/041; C10M2227/00; C10M2227/09; C10N; C10N2010/00; C10N2010/02; C10N2010/04; C10N2010/10; C10N2010/12; C10N2010/14; C10N2010/16; C10N2040/00; C10N2040/25; C10N2040/251; C10N2040/255; C10N2040/28; C10N2070/00; C10N2070/02; F; F02; F02B; F02B3/00; F02B3/06
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
131 words
An oil-soluble macrocyclic polyamine compound being a member of the group of compounds and mixtures thereof having the formulas: and where R' is hydrogen or lower C l -C 12 alkyl, R is a hydrocarbon substituent having 2 to 15,000 carbon atoms, R" is a hydrocarbon substituent of 4 to 15,000 carbon atoms, Z may be -CH 2 CH 2 CH 2 -; -(CH 2 CH 2 CH 2 NH) n CH 2 CH 2 CH 2 - where n is 1-6; or (CH 2 CH 2 CH 2 NH) m CH 2 (CH 2 ) p (NH-CH 2 CH 2 CH 2 ) m' - where m and m' are each at least 1 and m + m' is 1-5, p is 1 - 4 , and a is 1-20.
Claim 2
Dependent Claim
131 words
An oil-soluble macrocyclic polyamine compound being a member of the group of compounds and mixtures thereof having the formulas: and where R' is hydrogen or lower C l -C 12 alkyl, R is a hydrocarbon substituent having 2 to 15,000 carbon atoms, R" is a hydrocarbon substituent of 4 to 15,000 carbon atoms, Z may be -CH 2 CH 2 CH 2 -; -(CH 2 CH 2 CH 2 NH) n CH 2 CH 2 CH 2 - where n is 1-6; or (CH 2 CH 2 CH 2 NH) m CH 2 (CH 2 ) p (NH-CH 2 CH 2 CH 2 ) m' - where m and m' are each at least 1 and m + m' is 1-5, p is 1 - 4 , and a is 1-20.
Claim 3
Dependent Claim
19 words
The compound of claim 1 wherein R is a polyisobutylene of Mn 900 to 2,000 and R' is hydrogen.
Claim 4
Dependent Claim
19 words
The compound of claim 1 wherein R is an ethylene propylene copolymer or terpolymer of Mn 10,000 to 80,000.
Claim 5
Dependent Claim
34 words
The compound of claim 1 wherein Z is -CH 2 CH 2 CH 2 - or CH 2 CH 2 CH 2 (NHCH 2 CH 2 CH 2 ) n wherein n is 1-5.
Claim 6
Dependent Claim
23 words
The compound of claim 1 where a is 1-8 and R is an ethylene propylene copolymer or terpolymer of Mn 10,000 to 200,000.
Claim 7
Dependent Claim
12 words
The compound of claim 5 wherein R is a styrene isoprene copolymer.
Claim 8
Dependent Claim
77 words
An oil-soluble macrocyclic polyamine compound having the formula where R is a hydrocarbon having 2 to 15,000 carbon atoms and Z may be -CH 2 CH 2 CH 2 -; (CH 2 CH 2 CH 2 NH) n CH 2 CH 2 CH 2 - where n is 1-6 or (CH 2 CH 2 CH 2 NH) m CH 2 CH 2 (NH-CH 2 CH 2 CH 2 ) m ,- wherein m + m' is 1-5.
Claim 9
Dependent Claim
77 words
An oil-soluble macrocyclic polyamine compound having the formula where R is a hydrocarbon having 2 to 15,000 carbon atoms and Z may be -CH 2 CH 2 CH 2 -; (CH 2 CH 2 CH 2 NH) n CH 2 CH 2 CH 2 - where n is 1-6 or (CH 2 CH 2 CH 2 NH) m CH 2 CH 2 (NH-CH 2 CH 2 CH 2 ) m ,- wherein m + m' is 1-5.
Claim 10
Dependent Claim
81 words
An oil-soluble macrocyclic polayamine compound having the formula: wherein R is hydrocarbon having 2 to 15,000 carbon atoms, b may be 2 -150, Z may be -CH 2 CH 2 CH 2 -; (CH 2 CH 2 CH 2 NH) n CH 2 CH 2 CH 2 - wherein n is 1-6 or (CH 2 CH 2 CH 2 NH) m CH 2 CH 2 ( NH -CH 2 CH 2 CH 2 ) m ,- wherein m + m'is 1-5.
Claim 11
Dependent Claim
81 words
An oil-soluble macrocyclic polayamine compound having the formula: wherein R is hydrocarbon having 2 to 15,000 carbon atoms, b may be 2 -150, Z may be -CH 2 CH 2 CH 2 -; (CH 2 CH 2 CH 2 NH) n CH 2 CH 2 CH 2 - wherein n is 1-6 or (CH 2 CH 2 CH 2 NH) m CH 2 CH 2 ( NH -CH 2 CH 2 CH 2 ) m ,- wherein m + m'is 1-5.
Claim 12
Dependent Claim
16 words
The compound of claims 1-8 which has been post-treated with a complex-forming metal or boron reactant.
Claim 13
Dependent Claim
24 words
The compound of claim 9 wherein the post-treatment is conducted with a boron oxide, boron oxide hydrate, boron halide, boron ester or boron acid.
Claim 14
Dependent Claim
20 words
The compound of claim 9 which has been post-treated with 10 to 50 mole % of a polyisobutenyl -succinic anhydride.
Claim 15
Dependent Claim
64 words
An oil soluble macrocyclic polaymine compound being the reaction product of a hydrocarbon succinic anhydride or carboxylic acid having 8 to 15,000 carbon atoms with an aza macrocyclic compound having at least 2 NH groups and represented by the formula where U, V and W may be NH, S or O, n and m are integers of 1 to 4, alkylene is C 2-C4.
Claim 16
Dependent Claim
64 words
An oil soluble macrocyclic polaymine compound being the reaction product of a hydrocarbon succinic anhydride or carboxylic acid having 8 to 15,000 carbon atoms with an aza macrocyclic compound having at least 2 NH groups and represented by the formula where U, V and W may be NH, S or O, n and m are integers of 1 to 4, alkylene is C 2-C4.
Claim 17
Dependent Claim
17 words
The compound of claim 12 wherein the aza compound is 1,4,8,11-tetraazacyclotetradecane, 1,4,7,10-tetraazacyclododecane, 1,4,7,10-tetraazacyclotridecane, 1,4,8,12-tetraazacyclopentadecane, 1,5,9,13-tetraazacyclohexadecane or 1,4,7,10,13,16-hexaazacyclooctadecane.
Claim 18
Dependent Claim
58 words
14 An oil soluble polycyclic polyamine compound being the reaction product of a hydrocarbon succinic anhydride or carboxylic acid having 8 to 15,000 carbon atoms with an aza polycyclic ring compound containing 2 to 3 rings having 5 or 6 atoms per ring including 3 to 4 nitrogen atoms at least one of which is an NH group.
Claim 19
Dependent Claim
58 words
14 An oil soluble polycyclic polyamine compound being the reaction product of a hydrocarbon succinic anhydride or carboxylic acid having 8 to 15,000 carbon atoms with an aza polycyclic ring compound containing 2 to 3 rings having 5 or 6 atoms per ring including 3 to 4 nitrogen atoms at least one of which is an NH group.
Claim 20
Dependent Claim
27 words
15 A lubricating oil composition comprising a major amount of an oil of lubricating viscosity and 0.01 to 20 wt% of the macrocyclic compounds of claims 1-14.
Claim 21
Dependent Claim
25 words
16 A fuel composition comprising a major amount of a hydrocarbon fuel containing about 0.001 to about 1 wt.% of the compound of claims 1-14.
Claim 22
Dependent Claim
21 words
17 The use as an additive for lubricating oil of a compound according to any one of claims 1 to 14.
Claim 23
Dependent Claim
20 words
18 The use as an additive for fuels of a compound according to any one of claims 1 to 14.
Claim 24
Independent Claim
220 words
A method for preparing in a cyclodehydration reaction an oil-soluble hydrocarbon substituted macrocyclic polyamine compound comprising (i) in a first step reacting a poly 3-aminopropyl amine compound of the formula NH 2 -Z-NH 2 wherein Z may be -CH 2 CH 2 CH 2 -; (CH 2 CH 2 CH 2 NH) n CH 2 CH 2 CH 2 - wherein n is 1-6 or (CH 2 CH 2 CH 2 NH m CH 2 (CH 2 ) p (NH-CH 2 CH 2 CH 2 ) m ,- wherein p is 1-4 and m and m' are each at least 1 and m + m' is 1- 5 with a C 2 -C 15,000 monocarboxylic acid or polycarboxylic acid or C 2 -C 15,000 hydrocarbon substituted succinic anhydride, by addition of said carboxylic acid-or succinic anhydride to an initial excess of said amine compound at a rate such that there is formed an amic acid salt intermediate from said anhydride or an amine carboxylate salt intermediate from said carboxylate and at a temperature of about 20°C up to about 100°C in an inert solvent and, after said addition is complete (ii) in a second step maintaining the temperature of the reaction mixture at about 130°C to 250°C thereby causing cyclodehydration of said intermediates and formation of the macrocyclic polyamine compound.
Claim 25
Independent Claim
220 words
A method for preparing in a cyclodehydration reaction an oil-soluble hydrocarbon substituted macrocyclic polyamine compound comprising (i) in a first step reacting a poly 3-aminopropyl amine compound of the formula NH 2 -Z-NH 2 wherein Z may be -CH 2 CH 2 CH 2 -; (CH 2 CH 2 CH 2 NH) n CH 2 CH 2 CH 2 - wherein n is 1-6 or (CH 2 CH 2 CH 2 NH m CH 2 (CH 2 ) p (NH-CH 2 CH 2 CH 2 ) m ,- wherein p is 1-4 and m and m' are each at least 1 and m + m' is 1- 5 with a C 2 -C 15,000 monocarboxylic acid or polycarboxylic acid or C 2 -C 15,000 hydrocarbon substituted succinic anhydride, by addition of said carboxylic acid-or succinic anhydride to an initial excess of said amine compound at a rate such that there is formed an amic acid salt intermediate from said anhydride or an amine carboxylate salt intermediate from said carboxylate and at a temperature of about 20°C up to about 100°C in an inert solvent and, after said addition is complete (ii) in a second step maintaining the temperature of the reaction mixture at about 130°C to 250°C thereby causing cyclodehydration of said intermediates and formation of the macrocyclic polyamine compound.
Claim 26
Dependent Claim
20 words
20 The method of claim 19 wherein said second step is conducted at a temperature of about 140°C to 175°C.
Claim 27
Dependent Claim
43 words
The method of claim 19 which further comprises the step of heat soaking the reaction mixture at a temperature of 80°C to 130°C for 1 to 3 hours prior to increasing the temperature to cause cyclodehyration and formation of the macrocyclic polyamine compound.
Claim 28
Dependent Claim
24 words
22 The method of claim 21 wherein cyclodehydration is conducted at a temperature at least 20°C higher than the temperature of said heat soaking.
Claim 29
Dependent Claim
21 words
23 The method of claims 19 to 22 wherein the hydrocarbon succinic anhydride is polyisobutenyl succinic anhydride of Mn=900 - 2,000.
Claim 30
Dependent Claim
31 words
24 The method of claim 23 wherein the heat soaking is conducted at a temperature of 80°C to 110°C and the cyclodehydration is conducted at a temperature of 175°C to 180°C.
Claim 31
Dependent Claim
28 words
25 The method of claim 19 wherein a strong acid catalyst is added to the amine prior to adding said carboxylic acid or succinic anhydride to said amine.
Claim 32
Dependent Claim
17 words
26 The method of claim 25 wherein said acid is an oil soluble alkyl benzene sulfonic acid.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
Maintenance schedule is calculated for granted US utility patents.