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US4119552A Expired / Lapsed US ⏱️ 0.0 years remaining

Lubricant additive

Assignee: Edwin Cooper and Co Ltd
•
Filing: 1977-02-22
•
Granted: 1978-10-10
•
Expires: 1997-02-22
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Abstract

Abstract The reaction of a boron compound (e.g., boric acid) with an alkylphenoxy alkanoic acid amide (polyisobutylphenoxyacetamide of tetraethylenepentamine) forms a boronated product useful as a lubricating oil dispersant having improved properties.

Inventors

  • 👤 Bryan Terence Davis
  • 👤 Monty Frederick Crook

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 20:01
CPC Classifications
C; C10; C10M; C10M135/00; C10M135/20; C10M135/28; C10M135/30; C07; C07F; C07F5/00; C07F5/02; C07F5/022; C08; C08F; C08F8/00; C08F8/42; C10M133/00; C10M133/52; C10M133/56; C10M2205/00; C10M2205/02; C10M2205/026; C10M2205/06; C10M2207/00; C10M2207/02; C10M2207/023; C10M2207/024; C10M2207/027; C10M2207/028; C10M2209/00; C10M2209/02; C10M2209/08; C10M2209/084; C10M2215/00; C10M2215/02; C10M2215/06; C10M2215/062; C10M2215/22; C10M2215/221; C10M2215/225; C10M2215/226; C10M2215/24; C10M2215/30; C10M2219/00; C10M2219/02; C10M2219/022; C10M2219/04; C10M2219/044; C10M2219/046; C10M2219/08; C10M2219/082; C10M2219/087; C10M2219/088; C10M2219/089; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/045; C10M2223/12; C10M2225/00; C10M2225/04; C10M2225/041; C10M2227/00; C10M2227/06; C10M2227/061; C10M2227/063; C10N; C10N2010/00; C10N2010/04; C10N2070/00; C10N2070/02

Claims Analysis

Total Claims: 24
Claim 1
Independent Claim 417 words
A boronated product useful as a lubricating oil dispersant made by reacting an initial compound having the formula: ##STR17## wherein: (a) each R 3 is the same or different and is a hydrogen atom, an alkyl group containing from 1 to about 16 carbon atoms, a halogen atom, or one R 3 group in the ortho position relative to the oxygen atom is a group of the formula: ##STR18## in which (i) n is an integer from 1 to 6, (ii) each Z is the same or different and is a methylene group or a sulfur chain of formula -S) m wherein m is from 1 to 4, (iii) each R 4 is the same or different and is a hydrogen atom, an alkyl group containing from 1 to 16 carbon atoms, a halogen atom, a hydroxyl group or a group of formula ##STR19## (iv) each R 5 is the same or different and is a hydrogen atom, an alkyl group containing from 1 to 16 carbon atoms, a halogen atom, or a hydroxyl group, provided that one of, but not more than one of, R 4 and R 5 is a hydroxyl group, (v) each R 6 is the same or different and is a hydrogen atom, an alkyl group containing 1 to 29 carbon atoms, a halogen atom or is as R 2 , provided that one group R 3 in the ortho position relative to the oxygen atom attached to the aromatic nucleus is a hydrogen, a halogen, or a methyl or ethyl group, (b) each R is the same or different and is a straight or branched chain alkylene group containing from 1 to 20 carbon atoms, (c) each R 1 is the same or different and is a hydrogen atom or the ester residue of an alkanol containing from 1 to 5 carbon atoms, and (d) each R 2 is the same or different and is an alkyl group containing at least 30 carbon atoms; with about 0.5 to 10 equivalents per mole of said initial compound of an amine containing a reactive hydrogen atom bonded to nitrogen to form an amide and reacting said amide with a boron compound capable of introducing boron into the molecule, said boron compound being selected from the group consisting of boron acids, salts of boron acids, esters of boron acids, boron oxides, boron halides and boron salts of oxygen acids, to obtain a boronated product containing at least 0.01 atoms of boron per nitrogen atom.
Claim 2
Dependent Claim 417 words
A boronated product useful as a lubricating oil dispersant made by reacting an initial compound having the formula: ##STR17## wherein: (a) each R 3 is the same or different and is a hydrogen atom, an alkyl group containing from 1 to about 16 carbon atoms, a halogen atom, or one R 3 group in the ortho position relative to the oxygen atom is a group of the formula: ##STR18## in which (i) n is an integer from 1 to 6, (ii) each Z is the same or different and is a methylene group or a sulfur chain of formula -S) m wherein m is from 1 to 4, (iii) each R 4 is the same or different and is a hydrogen atom, an alkyl group containing from 1 to 16 carbon atoms, a halogen atom, a hydroxyl group or a group of formula ##STR19## (iv) each R 5 is the same or different and is a hydrogen atom, an alkyl group containing from 1 to 16 carbon atoms, a halogen atom, or a hydroxyl group, provided that one of, but not more than one of, R 4 and R 5 is a hydroxyl group, (v) each R 6 is the same or different and is a hydrogen atom, an alkyl group containing 1 to 29 carbon atoms, a halogen atom or is as R 2 , provided that one group R 3 in the ortho position relative to the oxygen atom attached to the aromatic nucleus is a hydrogen, a halogen, or a methyl or ethyl group, (b) each R is the same or different and is a straight or branched chain alkylene group containing from 1 to 20 carbon atoms, (c) each R 1 is the same or different and is a hydrogen atom or the ester residue of an alkanol containing from 1 to 5 carbon atoms, and (d) each R 2 is the same or different and is an alkyl group containing at least 30 carbon atoms; with about 0.5 to 10 equivalents per mole of said initial compound of an amine containing a reactive hydrogen atom bonded to nitrogen to form an amide and reacting said amide with a boron compound capable of introducing boron into the molecule, said boron compound being selected from the group consisting of boron acids, salts of boron acids, esters of boron acids, boron oxides, boron halides and boron salts of oxygen acids, to obtain a boronated product containing at least 0.01 atoms of boron per nitrogen atom.
Claim 3
Dependent Claim 13 words
A boronated product of claim 1 wherein R 3 is a hydrogen atom.
Claim 4
Dependent Claim 12 words
A boronated product of claim 2 wherein R is a methylene group.
Claim 5
Dependent Claim 17 words
A boronated product of claim 3 wherein R 2 is a polyolefin group containing 50-200 carbon atoms.
Claim 6
Dependent Claim 22 words
A boronated product of claim 4 wherein R 1 is the ester residue of an alkanol containing 1 to 5 carbon atoms.
Claim 7
Dependent Claim 13 words
A boronated product of claim 4 wherein said amine is an alkylene polyamine.
Claim 8
Dependent Claim 13 words
A boronated product of claim 5 wherein said amine is an alkylene polyamine.
Claim 9
Dependent Claim 14 words
A boronated product of claim 6 wherein said boron compound is a boron acid.
Claim 10
Dependent Claim 14 words
A boronated product of claim 7 wherein said boron compound is a boron acid.
Claim 11
Dependent Claim 14 words
A boronated product of claim 9 wherein said boron acid is a boric acid.
Claim 12
Dependent Claim 418 words
A process for making a boronated lubricating oil additive, said process comprising reacting an initial compound having the formula: ##STR20## wherein: (a) each R 3 is the same or different and is a hydrogen atom, an alkyl group containing from 1 to about 16 carbon atoms, a halogen atom, or one R 3 group in the ortho position relative to the oxygen atom is a group of the formula: ##STR21## in which (i) n is an integer from 1 to 6, (ii) each Z is the same or different and is a methylene group or a sulfur chain of formula -S) m wherein m is from 1 to 4, (iii) each R 4 is the same or different and is a hydrogen atom, an alkyl group containing from 1 to 16 carbon atoms, a halogen atom, a hydroxyl group or a group of formula ##STR22## (iv) each R 5 is the same or different and is a hydrogen atom, an alkyl group containing from 1 to 16 carbon atoms, a halogen atom, or a hydroxyl group, provided that one of, but not more than one of, R 4 and R 5 is a hydroxyl group, (v) each R 6 is the same or different and is a hydrogen atom, an alkyl group containing 1 to 29 carbon atoms, a halogen atom or is as R 2 , provided that one group R 3 in the ortho position relative to the oxygen atom attached to the aromatic nucleus is a hydrogen, a halogen, or a methyl or ethyl group, (b) each R is the same or different and is a straight or branched chain alkylene group containing from 1 to 20 carbon atoms, (c) each R 1 is the same or different and is a hydrogen atom or the ester residue of an alkanol containing from 1 to 5 carbon atoms, and (d) each R 2 is the same or different and is an alkyl group containing at least 30 carbon atoms; with about 0.5 to 10 equivalents per mole of said initial compound of an amine containing a reactive hydrogen atom bonded to nitrogen to form an amide and reacting said amide with a boron compound capable of introducing boron into the molecule, said boron compound being selected from the group consisting of boron acids, salts of boron acids, esters of boron acids, boron oxides, boron halides and boron salts of oxygen acids, to obtain a boronated product containing at least 0.01 atoms of boron per nitrogen atom.
Claim 13
Dependent Claim 418 words
A process for making a boronated lubricating oil additive, said process comprising reacting an initial compound having the formula: ##STR20## wherein: (a) each R 3 is the same or different and is a hydrogen atom, an alkyl group containing from 1 to about 16 carbon atoms, a halogen atom, or one R 3 group in the ortho position relative to the oxygen atom is a group of the formula: ##STR21## in which (i) n is an integer from 1 to 6, (ii) each Z is the same or different and is a methylene group or a sulfur chain of formula -S) m wherein m is from 1 to 4, (iii) each R 4 is the same or different and is a hydrogen atom, an alkyl group containing from 1 to 16 carbon atoms, a halogen atom, a hydroxyl group or a group of formula ##STR22## (iv) each R 5 is the same or different and is a hydrogen atom, an alkyl group containing from 1 to 16 carbon atoms, a halogen atom, or a hydroxyl group, provided that one of, but not more than one of, R 4 and R 5 is a hydroxyl group, (v) each R 6 is the same or different and is a hydrogen atom, an alkyl group containing 1 to 29 carbon atoms, a halogen atom or is as R 2 , provided that one group R 3 in the ortho position relative to the oxygen atom attached to the aromatic nucleus is a hydrogen, a halogen, or a methyl or ethyl group, (b) each R is the same or different and is a straight or branched chain alkylene group containing from 1 to 20 carbon atoms, (c) each R 1 is the same or different and is a hydrogen atom or the ester residue of an alkanol containing from 1 to 5 carbon atoms, and (d) each R 2 is the same or different and is an alkyl group containing at least 30 carbon atoms; with about 0.5 to 10 equivalents per mole of said initial compound of an amine containing a reactive hydrogen atom bonded to nitrogen to form an amide and reacting said amide with a boron compound capable of introducing boron into the molecule, said boron compound being selected from the group consisting of boron acids, salts of boron acids, esters of boron acids, boron oxides, boron halides and boron salts of oxygen acids, to obtain a boronated product containing at least 0.01 atoms of boron per nitrogen atom.
Claim 14
Dependent Claim 12 words
A process of claim 11 wherein R 3 is a hydrogen atom.
Claim 15
Dependent Claim 11 words
A process of claim 12 wherein R is a methylene group.
Claim 16
Dependent Claim 16 words
A process of claim 13 wherein R 2 is a polyolefin group containing 50-200 carbon atoms.
Claim 17
Dependent Claim 21 words
A process of claim 14 wherein R 1 is the ester residue of an alkanol containing 1 to 5 carbon atoms.
Claim 18
Dependent Claim 12 words
A process of claim 14 wherein said amine is an alkylene polyamine.
Claim 19
Dependent Claim 12 words
A process of claim 15 wherein said amine is an alkylene polyamine.
Claim 20
Dependent Claim 13 words
A process of claim 16 wherein said boron compound is a boron acid.
Claim 21
Dependent Claim 13 words
A process of claim 17 wherein said boron compound is a boron acid.
Claim 22
Dependent Claim 12 words
A process of claim 19 wherein said boron acid is boric acid.
Claim 23
Dependent Claim 22 words
A lubricating oil composition comprising a major amount of lubricating oil containing a dispersant amount of a boronated product of claim 1.
Claim 24
Dependent Claim 35 words
An additive concentrate which when added to lubricating oils will impart a balance of desirable properties to said lube oil, said concentration comprising about 15-50% diluent oil and about 5-75% boronated product of claim 1.

References Cited (Backward Citations)

US3445498A Cited
US3756953A Cited
US4016092A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-10-09 1982-04-10 1982-10-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-10-09 1986-04-10 1986-10-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-10-09 1990-04-10 1990-10-10 $7700.00 Window Closed / Lapsed

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