US4119552A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Lubricant additive
Assignee: Edwin Cooper and Co Ltd
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Filing: 1977-02-22
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Granted: 1978-10-10
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Expires: 1997-02-22
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)
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 |