US4120803A
Expired / Lapsed
US
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Lubricant composition containing a dispersant which is a condensation product of a copolymer, polyamine and a polycarboxylic acid
Assignee: Ethyl Corp
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Filing: 1976-11-15
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Granted: 1978-10-17
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Expires: 1996-11-15
Abstract
Abstract Mono-alkenes, aliphatic conjugated dienes and unsaturated fatty acids or esters thereof copolymerize with a Friedel-Crafts catalyst to yield a copolymer containing carboxylic acid or ester groups which are reacted with a polyamine to amidate the carboxyl group leaving free amine groups. The free amine groups are reacted with polycarboxylic acids to form inter- and intra-molecular bridged polyamides. These compounds are effective ashless dispersants in lubricating oil and have detergency properties in distillate fuels.
Inventors
- 👤 Robert E. Malec
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 00:28
CPC Classifications
C; C10; C10M; C10M149/00; C10M149/02; C10M149/06; C08; C08C; C08C19/00; C08C19/30; C08F; C08F236/00; C08F236/02; C08F236/04; C08F8/00; C08F8/10; C08F8/30; C08F8/32; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/22; C10L1/221; C08F2800/00; C08F2800/10; C08F2800/20; C08F2810/00; C08F2810/50; C10M2203/00; C10M2203/02; C10M2203/022; C10M2203/024; C10M2203/04; C10M2205/00; C10M2205/02; C10M2205/028; C10M2205/06; C10M2207/00; C10M2207/28; C10M2207/281; C10M2207/282; C10M2207/283; C10M2207/286; C10M2207/30; C10M2207/34; C10M2209/00; C10M2209/02; C10M2209/08; C10M2209/084; C10M2215/00; C10M2215/02; C10M2215/04; C10M2215/06; C10M2215/08; C10M2215/082; 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; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/045; C10N; C10N2010/00; C10N2010/04
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
295 words
An oil soluble lubricating oil dispersant which is made by: (A) copolymerizing a mixture of (i) about 3-55 mole percent of a material having the formula ##STR4## wherein R is an olefinically unsaturated hydrocarbon radical of up to 25 carbon atoms in which the carboxyl group is separated from all olefinic bonds by at least two carbon atoms and R 1 is selected from the group consisting of hydrogen and alkyl radicals containing 1 to about 15 carbon atoms, (ii) about 5 to 80 mole percent of a conjugated diethylenically unsaturated aliphatic hydrocarbon of 4 to about 12 carbon atoms, and (iii) about 92 to 15 mole percent of a monoalkene of 3 to about 30 carbon atoms, said material and said monoalkene being selected such that the total number of carbon atoms in these compounds is at least 12, said copolymerization being conducted at a temperature of about 0°-50° C. to form an intermediate copolymer, (B) reacting said intermediate copolymer with at least 1.1 equivalents of a hydrocarbyl polyamine containing 2 to about 12 carbon atoms and from about 2 to about 7 amine nitrogen atoms at a temperature of about 60°-320° C. to form an amidated copolymer which contains unreacted >NH and then (C) coupling said unreacted >NH by reaction at about 100°-300° C. with about 0.01-1.5 equivalents of a polycarboxylic acid per equivalent of said >NH group, said polycarboxylic acid being selected from the group consisting of (i) aliphatic dicarboxylic acid, and (ii) aromatic polycarboxylic acid containing an aryl group of about 6-10 carbon atoms and having 2 to 3 carboxylic groups bonded to said aryl group, said aliphatic dicarboxylic acid and aromatic polycarboxylic acid including precursor compound which yield said aliphatic dicarboxylic acid and said aromatic polycarboxylic acid under reaction conditions.
Claim 2
Dependent Claim
295 words
An oil soluble lubricating oil dispersant which is made by: (A) copolymerizing a mixture of (i) about 3-55 mole percent of a material having the formula ##STR4## wherein R is an olefinically unsaturated hydrocarbon radical of up to 25 carbon atoms in which the carboxyl group is separated from all olefinic bonds by at least two carbon atoms and R 1 is selected from the group consisting of hydrogen and alkyl radicals containing 1 to about 15 carbon atoms, (ii) about 5 to 80 mole percent of a conjugated diethylenically unsaturated aliphatic hydrocarbon of 4 to about 12 carbon atoms, and (iii) about 92 to 15 mole percent of a monoalkene of 3 to about 30 carbon atoms, said material and said monoalkene being selected such that the total number of carbon atoms in these compounds is at least 12, said copolymerization being conducted at a temperature of about 0°-50° C. to form an intermediate copolymer, (B) reacting said intermediate copolymer with at least 1.1 equivalents of a hydrocarbyl polyamine containing 2 to about 12 carbon atoms and from about 2 to about 7 amine nitrogen atoms at a temperature of about 60°-320° C. to form an amidated copolymer which contains unreacted >NH and then (C) coupling said unreacted >NH by reaction at about 100°-300° C. with about 0.01-1.5 equivalents of a polycarboxylic acid per equivalent of said >NH group, said polycarboxylic acid being selected from the group consisting of (i) aliphatic dicarboxylic acid, and (ii) aromatic polycarboxylic acid containing an aryl group of about 6-10 carbon atoms and having 2 to 3 carboxylic groups bonded to said aryl group, said aliphatic dicarboxylic acid and aromatic polycarboxylic acid including precursor compound which yield said aliphatic dicarboxylic acid and said aromatic polycarboxylic acid under reaction conditions.
Claim 3
Dependent Claim
15 words
A dispersant of claim 1 wherein said material is an alkyl ester of oleic acid.
Claim 4
Dependent Claim
13 words
A dispersant of claim 1 wherein said diethylenically unsaturated aliphatic hydrocarbon is butadiene.
Claim 5
Dependent Claim
13 words
A dispersant of claim 1 wherein said diethylenically unsaturated aliphatic hydrocarbon is isoprene.
Claim 6
Dependent Claim
24 words
A dispersant of claim 1 wherein said mono-alkene comprises about 20 to 100 mole percent mono-1-alkenes, the remainder of the mono-alkenes being internal mono-alkenes.
Claim 7
Dependent Claim
15 words
A dispersant of claim 5 wherein said mono-alkene comprises at least 35 mole percent mono-1-alkenes.
Claim 8
Dependent Claim
20 words
A dispersant of claim 5 wherein said mono-alkene is a mixture comprising mono-alkenes containing about 12 to 26 carbon atoms.
Claim 9
Dependent Claim
40 words
A dispersant of claim 1 wherein said polyamine is a C 2-4 alkylene polyamine containing from 1 to about 6 alkylene units and about 2 to 7 amine groups, each of said alkylene units being bonded to 2 amine groups.
Claim 10
Dependent Claim
56 words
A dispersant of claim 1 wherein said polycarboxylic acid is a saturated aliphatic dicarboxylic acid selected from the group consisting of oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid and sebacic acid including their anhydrides, ester and acid halides thereof which react to yield substantially the same product.
Claim 11
Dependent Claim
36 words
A dispersant of claim 9 wherein said aliphatic dicarboxylic acid is an alkenyl succinic acid or an anhydride, ester or acid halide thereof, said alkenyl group having a molecular weight of from about 50 to 5000.
Claim 12
Dependent Claim
12 words
A dispersant of claim 2 wherein said diethylenically unsaturated hydrocarbon is butadiene.
Claim 13
Dependent Claim
24 words
A dispersant of claim 11 wherein said mono-alkene comprises about 20 to 100 mole percent mono-1-alkenes, the remainder of the mono-alkenes being internal mono-alkenes.
Claim 14
Dependent Claim
20 words
A dispersant of claim 12 wherein said mono-alkene is a mixture comprising mono-alkenes containing about 12 to 26 carbon atoms.
Claim 15
Dependent Claim
27 words
A dispersant of claim 13 wherein said polyamine is selected from the group consisting of ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, pentaethylenehexamine, and mixtures thereof.
Claim 16
Dependent Claim
21 words
A dispersant of claim 14 wherein said polycarboxylic acid is an aliphatic dicarboxylic acid containing about 4 to 10 carbon atoms.
Claim 17
Dependent Claim
19 words
A dispersant of claim 15 wherein said dicarboxylic acid is succinic acid or its anhydride, ester or acid halide.
Claim 18
Dependent Claim
19 words
A dispersant of claim 15 wherein said dicarboxylic acid is adipic acid or its anhydride, ester or acid halide.
Claim 19
Dependent Claim
16 words
A lubricating oil composition containing a dispersant amount of an oil soluble dispersant of claim 1.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-10-16 | 1982-04-17 | 1982-10-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-10-16 | 1986-04-17 | 1986-10-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-10-16 | 1990-04-17 | 1990-10-17 | $7700.00 | Window Closed / Lapsed |