US4070370A
Expired / Lapsed
US
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Polyester lubricant additives, their preparation and compositions containing them
Assignee: Edwin Cooper and Co Ltd
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Filing: 1974-09-17
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Granted: 1978-01-24
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Expires: 1994-09-17
Abstract
Abstract Polyesters suitable for use as lubricant additives are prepared by reacting a di-carboxylic acid or anhydride having a branched chain alkyl or alkenyl substituent containing at least 30 carbon atoms with a compound having the formula: ##STR1## wherein R and R 1 are specified substituents which between them possess from 2 to 6 free hydroxyl groups. Lubricating compositions containing these polyester additives are also described.
Inventors
- 👤 John Scotchford Elliott
- 👤 Bryan Terence Davis
- 👤 Stephen Norman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 16:41
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/18; C07D207/22; C07D207/24; C07D207/26; C07D207/273; C07D207/277; C08; C08G; C08G63/00; C08G63/68; C08G63/685; C08G63/6854; C10; C10M; C10M133/00; C10M133/02; C10M133/38; C10M133/44; C10M2215/00; C10M2215/02; C10M2215/04; C10M2215/042; C10M2215/08; C10M2215/082; C10M2215/12; C10M2215/22; C10M2215/221; C10M2215/223; C10M2215/24; C10M2215/28; C10M2215/30; C10M2217/00; C10M2217/02; C10M2217/028; C10M2217/06; C10N; C10N2070/00; C10N2070/02
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
345 words
A polyester suitable for use as a lubricant additive which is the product of the reaction at elevated temperature from reflux up to about 210° C. with removal of water of a polyolefin substituted succinic acid or anhydride wherein said polyolefin substituent has a molecular weight of about 700-3,000 with a substituted carboxypyrrolidone of the following formula A ##STR14## in which a. R is selected from the group consisting of a hydrogen atom, an alkyl containing up to 8 carbon atoms, a phenyl group, a benzyl group, a hydroxyalkyl group containing 1-3 hydroxy radicals, a polyoxyalkylenealkyl group containing up to an average of about 2 oxyalkylene groups, a hydroxyalkylaminoalkyl group, a carboxypyrrolidone substituted C 2-6 alkyl group, and an imidazoline substituted C 1-4 alkyl group, b. each R 1 is independently selected from a group consisting of ##STR15## c. R 2 is alkylene containing 2-6 carbon atoms d. R 6 is selected from the group consisting of alkyl groups containing up to 8 carbon atoms, polyoxylalkyene alkyl groups containing up to an average of about 2 oxyalkylene groups, hydroxyalkyl groups containing 1-3 hydroxy radicals, imidazoline substituted C 1-4 alkyl groups, and groups having the formula ##STR16## in which the groups R and R 2 independently are as herein defined, e. R 7 is selected from the group consisting of alkyl groups containing up to 8 carbon atoms, hydroxyalkyl groups containing 1-3 hydroxy radicals, dialkylaminoalkyl groups, hydroxyalkylaminoalkyl groups, imidazoline substituted C 1-4 alkyl groups, groups having the formula ##STR17## and groups having the formula ##STR18## in which the groups R and R 2 independently are as herein defined, f. R 8 is selected from the group consisting of hydrogen, alkyl groups containing up to 8 carbon atoms, hydroxyalkyl groups containing up to 3 hydroxy groups, dialkyl aminoalkyl groups, imidazoline substituted C 1-4 alkyl groups, hydroxyalkylaminoalkyl groups and groups having the formula ##STR19## in which the groups R and R 2 independently are as herein defined, and g. provided that there are a total of from 2-6 free hydroxy groups on groups R and/or R 1 .
Claim 2
Dependent Claim
345 words
A polyester suitable for use as a lubricant additive which is the product of the reaction at elevated temperature from reflux up to about 210° C. with removal of water of a polyolefin substituted succinic acid or anhydride wherein said polyolefin substituent has a molecular weight of about 700-3,000 with a substituted carboxypyrrolidone of the following formula A ##STR14## in which a. R is selected from the group consisting of a hydrogen atom, an alkyl containing up to 8 carbon atoms, a phenyl group, a benzyl group, a hydroxyalkyl group containing 1-3 hydroxy radicals, a polyoxyalkylenealkyl group containing up to an average of about 2 oxyalkylene groups, a hydroxyalkylaminoalkyl group, a carboxypyrrolidone substituted C 2-6 alkyl group, and an imidazoline substituted C 1-4 alkyl group, b. each R 1 is independently selected from a group consisting of ##STR15## c. R 2 is alkylene containing 2-6 carbon atoms d. R 6 is selected from the group consisting of alkyl groups containing up to 8 carbon atoms, polyoxylalkyene alkyl groups containing up to an average of about 2 oxyalkylene groups, hydroxyalkyl groups containing 1-3 hydroxy radicals, imidazoline substituted C 1-4 alkyl groups, and groups having the formula ##STR16## in which the groups R and R 2 independently are as herein defined, e. R 7 is selected from the group consisting of alkyl groups containing up to 8 carbon atoms, hydroxyalkyl groups containing 1-3 hydroxy radicals, dialkylaminoalkyl groups, hydroxyalkylaminoalkyl groups, imidazoline substituted C 1-4 alkyl groups, groups having the formula ##STR17## and groups having the formula ##STR18## in which the groups R and R 2 independently are as herein defined, f. R 8 is selected from the group consisting of hydrogen, alkyl groups containing up to 8 carbon atoms, hydroxyalkyl groups containing up to 3 hydroxy groups, dialkyl aminoalkyl groups, imidazoline substituted C 1-4 alkyl groups, hydroxyalkylaminoalkyl groups and groups having the formula ##STR19## in which the groups R and R 2 independently are as herein defined, and g. provided that there are a total of from 2-6 free hydroxy groups on groups R and/or R 1 .
Claim 3
Dependent Claim
31 words
A polyester according to claim 1 wherein at least one of R, R 6 and R 7 and R 8 is a C 1-4 alkyl group substituted by at least one.
Claim 4
Dependent Claim
81 words
A polyester lubricant additive made by the process comprising reacting at elevated temperature of about 80°-180° C, a hydroxyamine compound selected from the group consisting of monohydroxyalkyl amines and dihydroxyalkyl aminoalkyl amines with itaconic acid or alkyl esters thereof to form an intermediate carboxypyrrolidone compound and reacting said intermediate at elevated temperature from reflux up to about 210° C. with removal of water with a polyolefin substituted succinic acid or anhydride, said polyolefin substituent having a molecular weight of about 700-3,000.
Claim 5
Dependent Claim
81 words
A polyester lubricant additive made by the process comprising reacting at elevated temperature of about 80°-180° C, a hydroxyamine compound selected from the group consisting of monohydroxyalkyl amines and dihydroxyalkyl aminoalkyl amines with itaconic acid or alkyl esters thereof to form an intermediate carboxypyrrolidone compound and reacting said intermediate at elevated temperature from reflux up to about 210° C. with removal of water with a polyolefin substituted succinic acid or anhydride, said polyolefin substituent having a molecular weight of about 700-3,000.
Claim 6
Dependent Claim
26 words
A polyester according to claim 1 wherein there are a total of from 3 to 6 free hydroxyl groups on groups R and/or R 1 .
Claim 7
Dependent Claim
23 words
A polyester according to claim 1 wherein the said polyolefin substituent of the said succinic acid or anhydride thereof is derived from polybutene.
Claim 8
Dependent Claim
20 words
A polyester of claim 3 wherein said hydroxyalkyl amine is monoethanol amine and said dihydroxyalkyl aminoalkylamine is 3-aminopropyl diethanol amine.
Claim 9
Dependent Claim
19 words
A polyester according to claim 1 wherein said polyolefin substituent has a molecular weight of from 900 to 1500.
Claim 10
Dependent Claim
70 words
A polyester according to claim 1 wherein: a. the substituents on the nitrogen atom and on the pendant carboxyl group of the substituted carboxypyrrolidone together have a total of from 3 to 6 hydroxyl groups; and b. the substituted carboxypyrrolidone is reacted with said polyolefin substituted succinic acid or anhydride thereof in an amount to provide a polyester containing from 1 to 4 free hydroxyl groups per succinic acid unit.
Claim 11
Dependent Claim
42 words
A polyester of claim 3 wherein said itaconic acid or ester is first reacted with said monohydroxyalkyl amine and then reacted with said dihydroxyalkyl aminoalkyl amine to form said carboxypyrrolidone intermediate which is reacted with said polyolefin substituted succinic acid or anhydride.
Claim 12
Dependent Claim
78 words
A polyester according to claim 1 which is the product of the reaction of a polybutenyl succinic anhydride in which the polybutenyl substituent has a molecular weight of from 900 to 1500, and a substituted carboxypyrrolidone of Formula A in which R is selected from the group consisting of said hydroxyalkyl group and said hydroxyalkylaminoalkyl group, R 1 is --NHR 7 and R 7 is selected from the group consisting of said hydroxyalkyl group and said hydroxyalkylaminoalkyl group.
Claim 13
Dependent Claim
53 words
A polyester of claim 1 which is the product of the reaction of a polybutenyl-substituted succinic acid or anhydride with a substituted carboxypyrrolidone of formula A, in which R is a hydroxyalkyl group and R 1 is the group ##STR20## in which R 7 is a hydroxyalkylaminoalkyl group and R 8 is hydrogen.
Claim 14
Dependent Claim
16 words
A polyester of claim 11 wherein R is a hydroxyethyl group and R 7 is N,N-dihydroxyethyl-3-aminopropyl.
Claim 15
Dependent Claim
21 words
A polyester of claim 9 wherein said monohydroxyalkyl amine is monoethanol amine and said dihydroxyalkyl aminoalkyl amine is 3-aminopropyl diethanol amine.
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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) | 1981-01-23 | 1981-07-25 | 1982-01-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-01-23 | 1985-07-25 | 1986-01-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-01-23 | 1989-07-25 | 1990-01-24 | $7700.00 | Window Closed / Lapsed |