US4097389A
Expired / Lapsed
US
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Novel amino alcohol reaction products and compositions containing the same
Assignee: Mobil Oil AS
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Filing: 1976-07-19
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Granted: 1978-06-27
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Expires: 1996-07-19
Abstract
Abstract Alkenylsuccinic anhydride is reacted with an amino alcohol, such as tris(hydroxymethyl)aminomethane, to provide intermediate reaction products from which novel derivatives are obtained by reacting the said intermediate product with boric acid or organoborates, organophosphonates and aldehydes. The intermediate reaction product prepared from tris(hydroxymethyl)aminomethane contains unexpectedly an oxazoline component when the reaction is carried out at 175 DEG C or below, preferably 100 DEG to 175 DEG C. The reaction products and their derivatives are particularly useful in lubricants, fuels or other industrial fluids as detergents.
Inventors
- 👤 Harry J. Andress, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 08:04
CPC Classifications
C; C10; C10M; C10M1/00; C10M1/08; C07; C07D; C07D263/00; C07D263/02; C07D263/08; C07D263/10; C07D263/12; C07D263/14; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6527; C07F9/653; C08; C08F; C08F8/00; C08F8/42; C08G; C08G63/00; C08G63/68; C08G63/685; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/22; C10L1/221; C10L1/232; C10L1/233; C10L1/234; C10L1/238; C10L1/26; C10L1/2691; C10L1/30; C10L1/301; C10L1/303; C10M2205/00; C10M2205/02; C10M2205/022; C10M2205/026; C10M2205/14; C10M2207/00; C10M2207/02; C10M2207/023; C10M2207/024; C10M2207/027; C10M2207/028; C10M2207/10; C10M2207/12; C10M2207/121; C10M2207/122; C10M2207/28; C10M2207/282; C10M2207/32; C10M2207/34; C10M2209/00; C10M2209/02; C10M2209/08; C10M2209/084; C10M2209/086; C10M2209/10; C10M2209/103; C10M2209/109; C10M2209/11; C10M2209/112; C10M2211/00; C10M2211/02; 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; C10M2217/04; C10M2217/042; C10M2217/043; C10M2217/046; C10M2217/06; C10M2219/00; C10M2219/04; C10M2219/044; C10M2219/046; C10M2219/08; C10M2219/082; C10M2219/087; C10M2219/088; C10M2219/089; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/041; C10M2223/042; C10M2223/045; C10M2223/06; C10M2223/061; C10M2223/065; C10M2223/08; C10M2223/12; C10M2225/00; C10M2225/04; C10M2225/041; C10M2227/00; C10M2227/06; C10M2227/061; C10M2229/00; C10M2229/02; C10M2229/04; C10M2229/05; C10N; C10N2010/00; C10N2010/04; C10N2040/00; C10N2040/02; C10N2040/04; C10N2040/042; C10N2040/044; C10N2040/046; C10N2040/08; C10N2040/25; C10N2040/252; C10N2040/253; C10N2050/00; C10N2050/10; C10N2070/00; C10N2070/02
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
221 words
A product prepared by reacting, at a temperature of from about 100° to about 200° C., one mole of alkenylsuccinic acid, anhydride or acyl halide with from 0.05 to 5 moles of a hydroxylated primary amine selected from the group consisting of 1-amino-2-hydroxypropane, 1-amino-3-hydroxypropane, 1-amino-2,3-dihydroxypropane, 1-amino-2,3,4-trihydroxybutane, 1-(hydroxymethyl)aminoethane, tris(hydroxymethyl)-aminomethane, 1,1-bis (hydroxymethyl)aminoethane and 1-(hydroxymethyl)benzylamine and reacting the resulting product with a reactant selected from the group consisting of (1) from about 1 to about 2 moles per mole of said product of a boron compound of the formula ##STR5## in which each R' is individually selected from the group consisting of hydrogen and a C 1 -C 20 alkyl, aralkyl or aralkyl group, (2) from about 1 mole to about 2 moles per mole of said product of an organophosphonate of the formula ##STR6## in which R' is individually selected from the group consisting of hydrogen and a C 1 -C 20 alkyl, arayl, aralkyl or alkaryl group (3) or from about 1 mole to about 2 moles per mole of said product of an aldehyde of the formula ##STR7## in which R' is selected from the group consisting of hydrogen and a C 1 -C 20 alkyl, aryl, aralkyl or alkaryl, the reaction of the boron, phosphonate or aldehyde with said product taking place at from about 50° to about 250° C.
Claim 2
Dependent Claim
221 words
A product prepared by reacting, at a temperature of from about 100° to about 200° C., one mole of alkenylsuccinic acid, anhydride or acyl halide with from 0.05 to 5 moles of a hydroxylated primary amine selected from the group consisting of 1-amino-2-hydroxypropane, 1-amino-3-hydroxypropane, 1-amino-2,3-dihydroxypropane, 1-amino-2,3,4-trihydroxybutane, 1-(hydroxymethyl)aminoethane, tris(hydroxymethyl)-aminomethane, 1,1-bis (hydroxymethyl)aminoethane and 1-(hydroxymethyl)benzylamine and reacting the resulting product with a reactant selected from the group consisting of (1) from about 1 to about 2 moles per mole of said product of a boron compound of the formula ##STR5## in which each R' is individually selected from the group consisting of hydrogen and a C 1 -C 20 alkyl, aralkyl or aralkyl group, (2) from about 1 mole to about 2 moles per mole of said product of an organophosphonate of the formula ##STR6## in which R' is individually selected from the group consisting of hydrogen and a C 1 -C 20 alkyl, arayl, aralkyl or alkaryl group (3) or from about 1 mole to about 2 moles per mole of said product of an aldehyde of the formula ##STR7## in which R' is selected from the group consisting of hydrogen and a C 1 -C 20 alkyl, aryl, aralkyl or alkaryl, the reaction of the boron, phosphonate or aldehyde with said product taking place at from about 50° to about 250° C.
Claim 3
Dependent Claim
10 words
The product of claim 1 wherein the amine is tris(hydroxymethyl)aminomethane.
Claim 4
Dependent Claim
20 words
The product of claim 1 wherein the reactant is selected from the group consisting of boric acid, dimethylphosphonate and formaldehyde.
Claim 5
Dependent Claim
11 words
The product of claim 3 wherein the reactant is boric acid.
Claim 6
Dependent Claim
11 words
The product of claim 3 wherein the reactant is dimethyl phosphonate.
Claim 7
Dependent Claim
10 words
The product of claim 3 wherein the reactant is formaldehyde.
Claim 8
Dependent Claim
241 words
An organic fluid composition comprising a major proportion of a mineral lubricating oil, a synthetic lubricating oil, a grease prepared from these or a normally liquid hydrocarbon fuel and a detergent amount of a product prepared by reacting one mole of alkenylsuccinic acid, anhydride or acyl halide with from 0.05 to 5 moles of a hydroxylated primary amine selected from the group consisting of 1-amino-2-hydroxypropane, 1-amine-3-hydroxypropane, 1-amine-2,3-dihydroxypropane, 1-amino-2,3,4-trihydroxybutane, 1-(hydroxymethyl)aminoethane, tris(hydroxymethyl)-aminomethane, 1,1-bis(hydroxymethyl)aminoethane and 1-(hydroxymethyl) benzylamine and reacting the resulting product with a reactant selected from the group consisting of (1) from about 1 to about 2 moles per mole of said product of a boron compound of the formula ##STR8## in which each R' is individually selected from the group consisting of hydrogen and a C 1 -C 20 alkyl, aralkyl or aralkyl group, (2) from about 1 mole to about 2 mole of said product of an organophosphonate of the formula ##STR9## in which R' is individually selected from the group consisting of hydrogen and a C 1 -C 20 alkyl, arayl, aralkyl or alkaryl group or (3) from about 1 mole to about 2 moles per mole of said product of an aldehyde of the formula ##STR10## in which R' is selected from the group consisting of hydrogen and a C 1 -C 20 alkyl, aryl, aralkyl or alkaryl, the reaction of the boron, phosphonate or aldehyde with said product taking place at from about 50° to about 250° C.
Claim 9
Dependent Claim
241 words
An organic fluid composition comprising a major proportion of a mineral lubricating oil, a synthetic lubricating oil, a grease prepared from these or a normally liquid hydrocarbon fuel and a detergent amount of a product prepared by reacting one mole of alkenylsuccinic acid, anhydride or acyl halide with from 0.05 to 5 moles of a hydroxylated primary amine selected from the group consisting of 1-amino-2-hydroxypropane, 1-amine-3-hydroxypropane, 1-amine-2,3-dihydroxypropane, 1-amino-2,3,4-trihydroxybutane, 1-(hydroxymethyl)aminoethane, tris(hydroxymethyl)-aminomethane, 1,1-bis(hydroxymethyl)aminoethane and 1-(hydroxymethyl) benzylamine and reacting the resulting product with a reactant selected from the group consisting of (1) from about 1 to about 2 moles per mole of said product of a boron compound of the formula ##STR8## in which each R' is individually selected from the group consisting of hydrogen and a C 1 -C 20 alkyl, aralkyl or aralkyl group, (2) from about 1 mole to about 2 mole of said product of an organophosphonate of the formula ##STR9## in which R' is individually selected from the group consisting of hydrogen and a C 1 -C 20 alkyl, arayl, aralkyl or alkaryl group or (3) from about 1 mole to about 2 moles per mole of said product of an aldehyde of the formula ##STR10## in which R' is selected from the group consisting of hydrogen and a C 1 -C 20 alkyl, aryl, aralkyl or alkaryl, the reaction of the boron, phosphonate or aldehyde with said product taking place at from about 50° to about 250° C.
Claim 10
Dependent Claim
10 words
The composition of claim 7 wherein the amine is tris(hydroxymethyl)aminomethane.
Claim 11
Dependent Claim
21 words
The composition of claim 7 wherein the reactant is selected from the group consisting of boric acid, dimethyl phosphonate and formaldehyde.
Claim 12
Dependent Claim
11 words
The composition of claim 9 wherein the reactant is boric acid.
Claim 13
Dependent Claim
11 words
The composition of claim 9 wherein the reactant is dimethyl phosphonate.
Claim 14
Dependent Claim
10 words
The composition of claim 9 wherein the reactant is formaldehyde.
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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) | 1981-06-26 | 1981-12-26 | 1982-06-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-26 | 1985-12-26 | 1986-06-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-26 | 1989-12-26 | 1990-06-27 | $7700.00 | Window Closed / Lapsed |