US4329249A
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US
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Carboxylic acid derivatives of alkanol tertiary monoamines and lubricants or functional fluids containing the same
Assignee: Lubrizol Corp
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Filing: 1978-09-27
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Granted: 1982-05-11
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Expires: 1998-09-27
Abstract
Abstract Nitrogen-containing phosphorus-free carboxylic acid derivatives made by reaction of an acylating agent with an alkanol tertiary monoamine are described. Typically the carboxylic acylating agent is an alkyl or alkenyl succinic anhydride containing about 20 to about 500 carbon atoms in the alkyl or alkenyl group. A typical amine is diethyl ethanol amine. These derivatives are useful in incorporating oil-soluble, water-insoluble functional additives, such as metal salts of acid phosphate and thiophosphate hydrocarbyl esters, into water-based functional fluids such as water-based hydraulic fluids.
Inventors
- 👤 John W. Forsberg
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 23:48
CPC Classifications
C; C08; C08F; C08F8/00; C08F8/44; C08F8/14; C08F8/30; C08F8/32; C10; C10M; C10M173/00; C10M2201/00; C10M2201/02; C10M2209/00; C10M2209/02; C10M2209/08; C10M2209/086; C10M2209/10; C10M2209/103; C10M2209/104; C10M2217/00; C10M2217/02; C10M2217/04; C10M2219/00; C10M2219/08; C10M2219/082; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/045; C10N; C10N2010/00; C10N2010/04; C10N2040/00; C10N2040/08; C10N2040/20; C10N2040/22; C10N2050/00; C10N2050/01; C10N2070/00; C10N2070/02
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
158 words
A nitrogen-containing, phosphorus-free carboxylic acid derivative made by reaction of a mixture consisting essentially of: (A) at least one carboxylic acid acylating agent having at least one hydrocarbyl-based substituent of about 50 to about 500 carbon atoms; (B) at least one alkanol tertiary monoamine having the formula ##STR4## wherein each R is a lower alkyl group and R' is an alkylene group of two to about eighteen carbon atoms; and (D) at least one other alkanol amine having the formula R 1 R 2 N-R 3 -OH, wherein R 1 and R 2 are each hydrogen, alkyl, alkenyl, hydroxy alkyl or hydroxy alkenyl and R 3 is alkylene; the amount of said other alkanol amine (D) being no more than about 50 mole percent of the amount of (B) and (D) combined; and the equivalent ratio of acylating agent (A) to the amount of (B) and (D) combined is in the range of about 1:0.5 to about 1:3.0.
Claim 2
Dependent Claim
158 words
A nitrogen-containing, phosphorus-free carboxylic acid derivative made by reaction of a mixture consisting essentially of: (A) at least one carboxylic acid acylating agent having at least one hydrocarbyl-based substituent of about 50 to about 500 carbon atoms; (B) at least one alkanol tertiary monoamine having the formula ##STR4## wherein each R is a lower alkyl group and R' is an alkylene group of two to about eighteen carbon atoms; and (D) at least one other alkanol amine having the formula R 1 R 2 N-R 3 -OH, wherein R 1 and R 2 are each hydrogen, alkyl, alkenyl, hydroxy alkyl or hydroxy alkenyl and R 3 is alkylene; the amount of said other alkanol amine (D) being no more than about 50 mole percent of the amount of (B) and (D) combined; and the equivalent ratio of acylating agent (A) to the amount of (B) and (D) combined is in the range of about 1:0.5 to about 1:3.0.
Claim 3
Dependent Claim
35 words
A derivative as claimed in claim 1 wherein said acylating agent (A) can be represented by the formula ##STR5## wherein hyd is an alkyl or alkenyl group of about 50 to about 500 carbon atoms.
Claim 4
Dependent Claim
21 words
A derivative as claimed in claim 2 wherein said monoamine (B) is diethyl ethanol amine and said derivative is an ester/salt.
Claim 5
Dependent Claim
21 words
A derivative as claimed in claim 2 wherein hyd is a poly(isobutene) group of about 50 to about 300 carbon atoms.
Claim 6
Dependent Claim
21 words
A derivative as claimed in claim 3 wherein hyd is a poly(isobutene) group of about 50 to about 300 carbon atoms.
Claim 7
Dependent Claim
33 words
A derivative as claimed in claim 1 wherein the equivalent ratio of acylating agent (A) to the amount of (B) and (D) combined is in the range of about 1:1 to about 1:2.5.
Claim 8
Dependent Claim
176 words
A water-based system useful as a lubricant or functional fluid comprising about 40 to about 70% of water, from 0 up to about 15% hydrocarbyl oil and a mixture comprising (a) from about 10 to about 40% of at least one normally water-insoluble, oil soluble functional additive selected from the group consisting of phosphorus and/or sulfur-containing anti-wear, extreme pressure, or load carrying agents, and (b) from about 40 to about 70% of a nitrogen-containing, phosphorus-free carboxylic acid derivative made by reaction of a mixture consisting essentially of (A) at least one carboxylic acid acylating agent and (B) at least one alkanol tertiary monoamine, said acylating agent (A) having at least one hydrocarbyl-based substituent of about 50 to about 500 carbon atoms and said monoamine (B) being represented by the formula ##STR6## wherein each R is a lower alkyl group and R' is an alkylene group of two to about eighteen carbon atoms, the equivalent ratio of acylating agent (A) to monoamine (B) used in the reaction being in the range of about 1:0.5 to about 1:3.0.
Claim 9
Dependent Claim
176 words
A water-based system useful as a lubricant or functional fluid comprising about 40 to about 70% of water, from 0 up to about 15% hydrocarbyl oil and a mixture comprising (a) from about 10 to about 40% of at least one normally water-insoluble, oil soluble functional additive selected from the group consisting of phosphorus and/or sulfur-containing anti-wear, extreme pressure, or load carrying agents, and (b) from about 40 to about 70% of a nitrogen-containing, phosphorus-free carboxylic acid derivative made by reaction of a mixture consisting essentially of (A) at least one carboxylic acid acylating agent and (B) at least one alkanol tertiary monoamine, said acylating agent (A) having at least one hydrocarbyl-based substituent of about 50 to about 500 carbon atoms and said monoamine (B) being represented by the formula ##STR6## wherein each R is a lower alkyl group and R' is an alkylene group of two to about eighteen carbon atoms, the equivalent ratio of acylating agent (A) to monoamine (B) used in the reaction being in the range of about 1:0.5 to about 1:3.0.
Claim 10
Dependent Claim
184 words
A water-based system useful as a lubricant or functional fluid comprising about 40 to about 70% of water, from 0 up to about 15% hydrocarbyl oil and a mixture comprising (a) from about 10 to about 40% of at least one normally water-insoluble, oil soluble functional additive selected from the group consisting of phosphorus and/or sulfur-containing anti-wear, extreme pressure, or load carrying agents, and (b) from about 40 to about 70% of a nitrogen-containing, phosphorus-free carboxylic acid derivative made by reaction of a mixture consisting essentially of (A) at least one carboxylic acid acylating agent and (B) at least one alkanol tertiary monoamine, said acylating agent (A) being represented by the formula ##STR7## wherein hyd is an alkyl or alkenyl group of about 50 to about 500 carbon atoms and said monoamine (B) being represented by the formula ##STR8## wherein each R is a lower alkyl group and R' is an alkylene group of two to about eighteen carbon atoms, the equivalent ratio of acylating agent (A) to monoamine (B) used in the reaction being in the range of about 1:0.5 to about 1:3.0.
Claim 11
Dependent Claim
184 words
A water-based system useful as a lubricant or functional fluid comprising about 40 to about 70% of water, from 0 up to about 15% hydrocarbyl oil and a mixture comprising (a) from about 10 to about 40% of at least one normally water-insoluble, oil soluble functional additive selected from the group consisting of phosphorus and/or sulfur-containing anti-wear, extreme pressure, or load carrying agents, and (b) from about 40 to about 70% of a nitrogen-containing, phosphorus-free carboxylic acid derivative made by reaction of a mixture consisting essentially of (A) at least one carboxylic acid acylating agent and (B) at least one alkanol tertiary monoamine, said acylating agent (A) being represented by the formula ##STR7## wherein hyd is an alkyl or alkenyl group of about 50 to about 500 carbon atoms and said monoamine (B) being represented by the formula ##STR8## wherein each R is a lower alkyl group and R' is an alkylene group of two to about eighteen carbon atoms, the equivalent ratio of acylating agent (A) to monoamine (B) used in the reaction being in the range of about 1:0.5 to about 1:3.0.
Claim 12
Dependent Claim
83 words
A water-based system useful as a lubricant or functional fluid comprising about 40 to about 70% of water, from 0 up to about 15% hydrocarbyl oil and a mixture comprising (a) from about 10 to about 40% of at least one normally water-insoluble, oil soluble functional additive selected from the group consisting of phosphorus and/or sulfur-containing anti-wear, extreme pressure, or load carrying agents, and (b) from about 40 to about 70% of a nitrogen-containing, phosphorus-free carboxylic acid derivative as claimed in claim 1.
Claim 13
Dependent Claim
23 words
The water-based system of any one of claims 7-9 wherein the mixture also contains (c) from about 5 to 20% of a surfactant.
Claim 14
Dependent Claim
19 words
A system as claimed in claim 8 wherein said monoamine (B) is diethylethanolamine and said derivative is an ester/salt.
Claim 15
Dependent Claim
21 words
A system as claimed in claim 8 wherein hyd is a poly(isobutene) group of about 50 to about 300 carbon atoms.
Claim 16
Dependent Claim
31 words
A system as claimed in claim 7 wherein the equivalent ratio of acylating agent (A) to monoamine (B) in the reaction is in the range of about 1:1 to about 1:2.5.
Claim 17
Dependent Claim
73 words
A nitrogen-containing, phosphorus-free carboxylic acid derivative made by reaction of a mixture consisting essentially of (a) at least one carboxylic acid acylating agent represented by the formula ##STR9## wherein hyd is an alkyl or alkenyl group of about 50 to about 200 carbon atoms and (B) a mixture of monoethanolamine and diethylethanolamine, the equivalent ratio of (A) to (B) used in the reaction being in the range of about 1:0.5 to about 1:3.0.
Claim 18
Dependent Claim
73 words
A nitrogen-containing, phosphorus-free carboxylic acid derivative made by reaction of a mixture consisting essentially of (a) at least one carboxylic acid acylating agent represented by the formula ##STR9## wherein hyd is an alkyl or alkenyl group of about 50 to about 200 carbon atoms and (B) a mixture of monoethanolamine and diethylethanolamine, the equivalent ratio of (A) to (B) used in the reaction being in the range of about 1:0.5 to about 1:3.0.
Claim 19
Dependent Claim
81 words
A water-based system useful as a lubricant or functional fluid comprising about 40% to about 70% of water, from 0 up to about 15% hydrocarbyl oil and a mixture comprising (a) from about 10% to about 40% of at least one normally water-insoluble, oil-soluble functional additive selected from the group consisting of phosphorus and/or sulfur-containing anti-wear, extreme pressure or load-carrying agents, and (b) from about 40% to about 70% of a nitrogen-containing, phosphorus-free carboxylic acid derivative as claimed in claim 14.
Claim 20
Dependent Claim
21 words
The water-based system of claim 15 wherein the mixture also contains (c) from about 5% to about 20% of a surfactant.
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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) | 1985-05-10 | 1985-11-09 | 1986-05-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-05-10 | 1989-11-09 | 1990-05-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-05-10 | 1993-11-09 | 1994-05-11 | $7700.00 | Window Closed / Lapsed |