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US4285824A Expired / Lapsed US ⏱️ 0.0 years remaining

Hydroxyalkyl hydroxy-aromatic condensation products as fuel and lubricant additives

Assignee: Lubrizol Corp
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Filing: 1980-02-22
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Granted: 1981-08-25
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Expires: 2000-02-22
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Abstract

Abstract Condensation products made by reacting an α-hydroxyalkyl hydroxy-aromatic compound also having at least one non-fused hydrocarbyl substituent with at least one olefinic nitrile, carboxylic acid or carboxylic acid derivative are useful as additives for fuels and lubricants. The total number of carbon atoms in the non-fused hydrocarbyl substituents is at least about 7 while the α-hydroxyalkyl group contains from 1 to about 36 carbons and the olefinic acid or nitrile reactant usually contains 2 to about 40 carbon atoms. Products made from hydroxymethyl alkyl-substituted phenols and α,β-olefinic acid derivatives such as maleic anhydride are particularly useful. Similarly useful post-treated products can be made from these condensation products by further reaction with alcohols, amines, metal salts or metals.

Inventors

  • 👤 Charles P. Bryant

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 23:22
CPC Classifications
C; C10; C10M; C10M159/00; C10M159/12; C08; C08F; C08F8/00; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/18; C10L1/1817; C10L1/22; C10L1/221; C10M2229/00; C10M2229/04; C10M2229/05

Claims Analysis

Total Claims: 47
Claim 1
Independent Claim 308 words
A post-treated product made by a process which comprises reacting a mono- or polyhydric alcohol, an epoxide, a C 1 - 30 monoamine, or a polyamine of the formula ##STR19## wherein each A is independently a hydrogen atom, a hydrocarbyl group of up to 30 carbon atoms or a hydroxy-substituted hydrocarbyl group of up to about ten carbon atoms containing one or two hydroxy groups, "Alkylene" is a divalent alkylene group of about one to ten carbon atoms and a is an average of integers between one and ten, and mixtures thereof, with a condensation product made by the process comprising reacting (A) at least one alpha hydroxy aromatic compound of the general formula ##STR20## wherein Ar is a hydrocarbyl aromatic nucleus of 6 to about 30 carbon atoms, or an analog of such an aromatic nucleus substituted with 1 to 3 lower alkoxy, lower alkylthio, chloro, or nitro substituents, each R is a nonfused hydrocarbyl group of about 25 to about 700 carbon atoms, each R' is independently a hydrogen atom, an alkyl group of 1 to 36 carbon atoms, or a halogen-substituted alkyl group of 1 to about 36 carbon atoms, n is 1 to 3 and m is 1 to 5 with the provisos that (i) the total number of carbon atoms in the R' groups does not exceed 36 and (ii) where m exceeds 1, one of the R groups can also be a ##STR21## group, with (B) at least one hydrocarbyl, alpha-beta olefinically unsaturated compound selected from the group consisting of C 2 - 40 nitriles, C 2 - 40 carboxylic acids and anhydrides, esters, amides and ammonium and metal salts of said C 2 - 40 carboxylic acids, the reaction of (A) with (B) resulting in the formation of carbon-to-carbon bond, said bond including the carbon of at least one ##STR22## group.
Claim 2
Dependent Claim 308 words
A post-treated product made by a process which comprises reacting a mono- or polyhydric alcohol, an epoxide, a C 1 - 30 monoamine, or a polyamine of the formula ##STR19## wherein each A is independently a hydrogen atom, a hydrocarbyl group of up to 30 carbon atoms or a hydroxy-substituted hydrocarbyl group of up to about ten carbon atoms containing one or two hydroxy groups, "Alkylene" is a divalent alkylene group of about one to ten carbon atoms and a is an average of integers between one and ten, and mixtures thereof, with a condensation product made by the process comprising reacting (A) at least one alpha hydroxy aromatic compound of the general formula ##STR20## wherein Ar is a hydrocarbyl aromatic nucleus of 6 to about 30 carbon atoms, or an analog of such an aromatic nucleus substituted with 1 to 3 lower alkoxy, lower alkylthio, chloro, or nitro substituents, each R is a nonfused hydrocarbyl group of about 25 to about 700 carbon atoms, each R' is independently a hydrogen atom, an alkyl group of 1 to 36 carbon atoms, or a halogen-substituted alkyl group of 1 to about 36 carbon atoms, n is 1 to 3 and m is 1 to 5 with the provisos that (i) the total number of carbon atoms in the R' groups does not exceed 36 and (ii) where m exceeds 1, one of the R groups can also be a ##STR21## group, with (B) at least one hydrocarbyl, alpha-beta olefinically unsaturated compound selected from the group consisting of C 2 - 40 nitriles, C 2 - 40 carboxylic acids and anhydrides, esters, amides and ammonium and metal salts of said C 2 - 40 carboxylic acids, the reaction of (A) with (B) resulting in the formation of carbon-to-carbon bond, said bond including the carbon of at least one ##STR22## group.
Claim 3
Dependent Claim 13 words
A composition as claimed in claim 1 wherein m is 1 or 2.
Claim 4
Dependent Claim 13 words
A composition as claimed in claim 2 wherein Ar is a benzene nucleus.
Claim 5
Dependent Claim 11 words
A composition as claimed in claim 3 wherein R' is hydrogen.
Claim 6
Dependent Claim 21 words
A composition as claimed in claim 4 wherein each R is a homo- or interpolymer of ethylene, propylene, butylene or isobutylene.
Claim 7
Dependent Claim 14 words
A composition as claimed in claim 5 wherein (B) is an acid or anhydride.
Claim 8
Dependent Claim 12 words
A composition as claimed in claim 6 wherein (B) is maleic anhydride.
Claim 9
Dependent Claim 56 words
A composition as claimed in claim 5 wherein Ar is a bridged moiety wherein two or more aromatic rings are connected through a bridging unit which is a covalent carbon-to-carbon bond, an oxygen atom, a sulfur atom, polysulfide, sulfinyl, sulfonyl, amino, methylene, substituted methylene groups, oxymethylene groups or a mixture of two or more of these.
Claim 10
Dependent Claim 29 words
A composition as claimed in claim 1, 2, 3 or 4 wherein the polyhydric alcohol contains from two to ten hydroxy groups and two to about 25 carbon atoms.
Claim 11
Dependent Claim 25 words
A composition as claimed in claim 5 wherein the polyhydric alcohol contains from two to ten hydroxy groups and two to about 25 carbon atoms.
Claim 12
Dependent Claim 25 words
A composition as claimed in claim 6 wherein the polyhydric alcohol contains from two to ten hydroxy groups and two to about 25 carbon atoms.
Claim 13
Dependent Claim 25 words
A composition as claimed in claim 7 wherein the polyhydric alcohol contains from two to ten hydroxy groups and two to about 25 carbon atoms.
Claim 14
Dependent Claim 25 words
A composition as claimed in claim 8 wherein the polyhydric alcohol contains from two to ten hydroxy groups and two to about 25 carbon atoms.
Claim 15
Dependent Claim 28 words
A lubricant composition comprising a major amount of at least one lubricating oil and a minor but engine sludge dispersing amount of the composition claimed in claim 1.
Claim 16
Dependent Claim 28 words
A lubricant composition comprising a major amount of at least one lubricating oil and a minor but engine sludge dispersing amount of the composition claimed in claim 4.
Claim 17
Dependent Claim 28 words
A lubricant composition comprising a major amount of at least one lubricating oil and a minor but engine sludge dispersing amount of the composition claimed in claim 5.
Claim 18
Dependent Claim 28 words
A lubricant composition comprising a major amount of at least one lubricating oil and a minor but engine sludge dispersing amount of the composition claimed in claim 6.
Claim 19
Dependent Claim 28 words
A lubricant composition comprising a major amount of at least one lubricating oil and a minor but engine sludge dispersing amount of the composition claimed in claim 7.
Claim 20
Dependent Claim 28 words
A lubricant composition comprising a major amount of at least one lubricating oil and a minor but engine sludge dispersing amount of the composition claimed in claim 8.
Claim 21
Dependent Claim 28 words
A lubricant composition comprising a major amount of at least one lubricating oil and a minor but engine sludge dispersing amount of the composition claimed in claim 9.
Claim 22
Dependent Claim 28 words
A lubricant composition comprising a major amount of at least one lubricating oil and a minor but engine sludge dispersing amount of the composition claimed in claim 10.
Claim 23
Dependent Claim 28 words
A lubricant composition comprising a major amount of at least one lubricating oil and a minor but engine sludge dispersing amount of the composition claimed in claim 11.
Claim 24
Dependent Claim 28 words
A lubricant composition comprising a major amount of at least one lubricating oil and a minor but engine sludge dispersing amount of the composition claimed in claim 12.
Claim 25
Dependent Claim 28 words
A lubricant composition comprising a major amount of at least one lubricating oil and a minor but engine sludge dispersing amount of the composition claimed in claim 13.
Claim 26
Dependent Claim 27 words
A fuel composition comprising a major amount of a normally liquid fuel and a minor but carburetor-cleaning or anti-rust amount of the composition claimed in claim 1.
Claim 27
Dependent Claim 27 words
A fuel composition comprising a major amount of a normally liquid fuel and a minor but carburetor-cleaning or anti-rust amount of the composition claimed in claim 4.
Claim 28
Dependent Claim 27 words
A fuel composition comprising a major amount of a normally liquid fuel and a minor but carburetor-cleaning or anti-rust amount of the composition claimed in claim 5.
Claim 29
Dependent Claim 27 words
A fuel composition comprising a major amount of a normally liquid fuel and a minor but carburetor-cleaning or anti-rust amount of the composition claimed in claim 6.
Claim 30
Dependent Claim 27 words
A fuel composition comprising a major amount of a normally liquid fuel and a minor but carburetor-cleaning or anti-rust amount of the composition claimed in claim 7.
Claim 31
Dependent Claim 27 words
A fuel composition comprising a major amount of a normally liquid fuel and a minor but carburetor-cleaning or anti-rust amount of the composition claimed in claim 8.
Claim 32
Dependent Claim 27 words
A fuel composition comprising a major amount of a normally liquid fuel and a minor but carburetor-cleaning or anti-rust amount of the composition claimed in claim 9.
Claim 33
Dependent Claim 27 words
A fuel composition comprising a major amount of a normally liquid fuel and a minor but carburetor-cleaning or anti-rust amount of the composition claimed in claim 10.
Claim 34
Dependent Claim 27 words
A fuel composition comprising a major amount of a normally liquid fuel and a minor but carburetor-cleaning or anti-rust amount of the composition claimed in claim 11.
Claim 35
Dependent Claim 27 words
A fuel composition comprising a major amount of a normally liquid fuel and a minor but carburetor-cleaning or anti-rust amount of the composition claimed in claim 12.
Claim 36
Dependent Claim 27 words
A fuel composition comprising a major amount of a normally liquid fuel and a minor but carburetor-cleaning or anti-rust amount of the composition claimed in claim 13.
Claim 37
Dependent Claim 20 words
An additive concentrate comprising about 20 to 90 percent of the composition claimed in claim 1 and an inert solvent/diluent.
Claim 38
Dependent Claim 20 words
An additive concentrate comprising about 20 to 90 percent of the composition claimed in claim 4 and an inert solvent/diluent.
Claim 39
Dependent Claim 20 words
An additive concentrate comprising about 20 to 90 percent of the composition claimed in claim 5 and an inert solvent/diluent.
Claim 40
Dependent Claim 20 words
An additive concentrate comprising about 20 to 90 percent of the composition claimed in claim 6 and an inert solvent/diluent.
Claim 41
Dependent Claim 20 words
An additive concentrate comprising about 20 to 90 percent of the composition claimed in claim 7 and an inert solvent/diluent.
Claim 42
Dependent Claim 20 words
An additive concentrate comprising about 20 to 90 percent of the composition claimed in claim 8 and an inert solvent/diluent.
Claim 43
Dependent Claim 20 words
An additive concentrate comprising about 20 to 90 percent of the composition claimed in claim 9 and an inert solvent/diluent.
Claim 44
Dependent Claim 20 words
An additive concentrate comprising about 20 to 90 percent of the composition claimed in claim 10 and an inert solvent/diluent.
Claim 45
Dependent Claim 20 words
An additive concentrate comprising about 20 to 90 percent of the composition claimed in claim 11 and an inert solvent/diluent.
Claim 46
Dependent Claim 20 words
An additive concentrate comprising about 20 to 90 percent of the composition claimed in claim 12 and an inert solvent/diluent.
Claim 47
Dependent Claim 20 words
An additive concentrate comprising about 20 to 90 percent of the composition claimed in claim 13 and an inert solvent/diluent.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-08-24 1985-02-23 1985-08-25 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-08-24 1989-02-23 1989-08-25 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-08-24 1993-02-23 1993-08-25 $7700.00 Window Closed / Lapsed

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