US4489194A
Expired / Lapsed
US
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Carboxylic acylating agents substituted with olefin polymers of high/low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
Assignee: Lubrizol Corp
•
Filing: 1982-08-09
•
Granted: 1984-12-18
•
Expires: 2002-08-09
Abstract
Abstract Hydrocarbyl substituted carboxylic acylating agents are made by reacting, optionally in the presence of chlorine or bromine, (A) one or more alpha-beta olefinically unsaturated carboxylic acid reagents containing 2 to about 20 carbon atoms, exclusive of the carboxyl-based groups with (B) one or more high molecular weight olefin polymers of more than 30 carbon atoms selected from the group consisting of (i) interpolymers of C 2-8 mono-1-olefins with C 12 -C 30 mono-olefins, (ii) mixtures of (a) homopolymers and/or interpolymers of C 2-8 mono-1-olefins with (b) homopolymers and/or interpolymers of C 12 -C 30 mono-olefins, and (iii) chlorinated or brominated analogs of (i) or (ii). This invention includes the acylated amine and/or alcohol derivatives of these hydrocarbyl-substituted carboxylic acid acylating agents and their use in lubricants and normally liquid fuels.
Inventors
- 👤 Katsumi Hayashi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 16:09
CPC Classifications
C; C10; C10M; C10M133/00; C10M133/52; C08; C08F; C08F8/00; C08F8/14; C08F8/18; C08F8/20; C08F8/22; C08F8/30; C08F8/32; C10M129/00; C10M129/86; C10M129/95; C08F2800/00; C08F2800/20
Claims Analysis
Total Claims: 46
Claim 1
Independent Claim
147 words
A composition comprising: the reaction product of (I): (A) one or more alpha-beta olefinically unsaturated carboxylic reagents containing two to about 20 carbon atoms exclusive of the carboxyl-based groups reacted with (B) one or more olefin polymers of at least 30 carbon atoms selected from the group consisting of (i) interpolymers of C 4 mono-1-olefins with C 12 -C 30 mono-olefins with the proviso that said interpolymers exclude interpolymers derived from ethylene, (ii) mixtures of (a) homopolymers and/or interpolymers of C 4 mono-1-olefins with (b) homopolymers and/or interpolymers of C 12 -C 30 mono-olefins and (iii) chlorinated or brominated analogs of (i) or (ii); reacted with (II) one or more amines, one or more alcohols, or a mixture of one or more amines and/or one or more alcohols; with the proviso that the reaction product of (I) and (II) is soluble in an oil of lubricating viscosity.
Claim 2
Dependent Claim
147 words
A composition comprising: the reaction product of (I): (A) one or more alpha-beta olefinically unsaturated carboxylic reagents containing two to about 20 carbon atoms exclusive of the carboxyl-based groups reacted with (B) one or more olefin polymers of at least 30 carbon atoms selected from the group consisting of (i) interpolymers of C 4 mono-1-olefins with C 12 -C 30 mono-olefins with the proviso that said interpolymers exclude interpolymers derived from ethylene, (ii) mixtures of (a) homopolymers and/or interpolymers of C 4 mono-1-olefins with (b) homopolymers and/or interpolymers of C 12 -C 30 mono-olefins and (iii) chlorinated or brominated analogs of (i) or (ii); reacted with (II) one or more amines, one or more alcohols, or a mixture of one or more amines and/or one or more alcohols; with the proviso that the reaction product of (I) and (II) is soluble in an oil of lubricating viscosity.
Claim 3
Dependent Claim
19 words
The composition of claim 1 wherein components (A) and (B) are reacted in the presence of chllorine or bromine.
Claim 4
Dependent Claim
12 words
The composition of claim 1 wherein component (A) is monobasic or polybasic.
Claim 5
Dependent Claim
18 words
The composition of claim 1 wherein component (A) is carboxylic acid or a functional derivative of carboxylic acid.
Claim 6
Dependent Claim
52 words
The composition of claim 1 wherein component (A) is represented by the formula ##STR22## wherein R is hydrogen or a saturated aliphatic or heterocyclic group, R 1 is hydrogen or a lower alkyl group and the total number of carbon atoms in R and R 1 does not exceed 18 carbon atoms.
Claim 7
Dependent Claim
21 words
The composition of claim 1 wherein component (A) is a dibasic carboxylic acid or a derivative of such dibasic carboxylic acid.
Claim 8
Dependent Claim
40 words
The composition of claim 1 wherein component (A) is a mono-, di-, tri- or tetracarboxylic acid, or a derivative of such acid selected from the group consisting of anhydride, ester, acylated nitrogen, acid halide, nitrile, ammonium salt and metal salts.
Claim 9
Dependent Claim
41 words
The composition of claim 1 wherein component (A) is selected from the group consisting of acrylic acid, methacrylic acid, fumaric acid, maleic acid, lower alkyl esters of such acids, maleic anhydride, and mixtures of two or more of any of these.
Claim 10
Dependent Claim
11 words
The composition of claim 1 wherein component (A) is maleic anhydride.
Claim 11
Dependent Claim
20 words
The composition of claim 1 wherein said C 4 mono-1-olefins are selected from the group consisting of 1-butene and isobutene.
Claim 12
Dependent Claim
43 words
The composition of claim 1 wherein said C 12-30 mono-olefins are selected from the group consisting of the following olefin mixtures: C 15-18 alpha-olefins; C 12-16 alpha-olefins; C 14-16 alpha-olefins; C 14-18 alpha-olefins; C 16-18 alpha-olefins; C 16-20 alpha-olefins; and C 22-28 alpha-olefins.
Claim 13
Dependent Claim
101 words
The composition of claim 1 wherein component (B) is one or a mixture of more than one olefin selected from the group consisting of C 4 mono-1-olefins polymerized with one or a mixture of more than one mono-olefin selected from the group consisting of C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C 20 , C 21 , C 22 , C 23 , C 24 , C 25 , C 26 , C 27 , C 28 , C 29 and C 30 mono-olefins.
Claim 14
Dependent Claim
18 words
The composition of claim 1 wherein component (B) has an average of from 30 to 3500 carbon atoms.
Claim 15
Dependent Claim
20 words
The composition of claim 1 wherein component (B) has an average of from about 50 to about 750 carbon atoms.
Claim 16
Dependent Claim
23 words
The composition of claim 1 wherein component (B) has a number average molecular weight in the range of about 420 to about 20,000.
Claim 17
Dependent Claim
23 words
The composition of claim 1 wherein component (B) has a weight average molecular weight in the range of about 800 to about 100,000.
Claim 18
Dependent Claim
24 words
The composition of claim 1 wherein component (B) has an inherent viscosity in the range of about 0.03 to about 1.5 deciliters per gram.
Claim 19
Dependent Claim
14 words
The composition of claim 1 wherein component (II) is a monoamine or a polyamine.
Claim 20
Dependent Claim
25 words
The composition of claim 1 wherein component (II) comprises at least one amine characterized by the presence within its structure of at least H--N< group.
Claim 21
Dependent Claim
14 words
The composition of claim 1 wherein component (II) is hydrazine or a substituted hydrazine.
Claim 22
Dependent Claim
15 words
The composition of claim 1 wherein component (II) has at least one primary amino group.
Claim 23
Dependent Claim
17 words
The composition of claim 1 wherein component (II) is a polyamine containing at least two H--N< groups.
Claim 24
Dependent Claim
29 words
The composition of claim 1 wherein component (II) is a polyamine amine group containing at least two H--N< groups, either or both of which are primary or secondary amines.
Claim 25
Dependent Claim
14 words
The composition of claim 1 wherein component (II) is a monohydric or polyhydric alcohol.
Claim 26
Dependent Claim
18 words
The composition of claim 1 wherein component (II) is an aliphatic monoamine of up to 40 carbon atoms.
Claim 27
Dependent Claim
12 words
The composition of claim 1 wherein component (II) is a cycloaliphatic monoamine.
Claim 28
Dependent Claim
12 words
The composition of claim 1 wherein component (II) is an aromatic monoamine.
Claim 29
Dependent Claim
15 words
The composition of claim 1 wherein component (II) is an aliphatic, cycloaliphatic or aromatic polyamine.
Claim 30
Dependent Claim
11 words
The composition of claim 1 wherein component (II) is a hydroxyamine.
Claim 31
Dependent Claim
12 words
The composition of claim 1 wherein component (II) is an aminosulfonic acid.
Claim 32
Dependent Claim
31 words
The composition of claim 1 wherein component (II) is a hydrocarbyl mono- polyamine prepared by reacting a chlorinated polyolefin having a molecular weight of at least 400 with ammonia or amine.
Claim 33
Dependent Claim
13 words
The composition of claim 1 wherein component (II) is a branched polyalkylene polyamine.
Claim 34
Dependent Claim
33 words
The composition of claim 1 wherein component (II) is polyoxyalkylene diamine or polyoxyalkylene triamine, said diamine and said triamine having an average molecular weight in the range of about 200 to about 4000.
Claim 35
Dependent Claim
57 words
The composition of claim 1 wherin component (II) is an alkylene polyamine of the formula ##STR23## wherein n is a number from 1 to 10, each R" is independently a hydrogen atom, a hydrocarbyl group or a hydroxy-substituted hydrocarbyl group having up to 30 carbon atoms, and the Alkylene group has from 1 to 10 carbon atoms.
Claim 36
Dependent Claim
11 words
The composition of claim 1 wherein component (II) is ethylene polyamine.
Claim 37
Dependent Claim
23 words
The composition of claim 1 wherein component (II) is a hydroxyalkyl alkylene polyamine having one or more hydroxyalkyl substituents on the nitrogen atoms.
Claim 38
Dependent Claim
42 words
The composition of claim 1 wherein component (II) is represented by the formula R.sub.1`--(OH).sub.m wherein R 1 is a monovalent or polyvalent organic radical joined to the --OH groups through carbon-to-oxygen bonds and m is an integer of from 1 to 10.
Claim 39
Dependent Claim
133 words
The composition of claim 1 wherein component (II) is a polyoxyalkylene alcohol wherein a hydroxy substituted compound, which is represented by the formula R.sub.2 --(OH).sub.q ( 1) wherein q is an integer of from 1 to 6 and R 2 is the residue of a mono- or polyhydric alcohol or mono- or polyhydroxy phenyl or naphthol, is reacted with an alkylene oxide, which is represented by the formula ##STR24## wherein R 3 is an alkyl group of up to four carbon atoms and R 4 is hydrogen or an alkyl group of up to four carbon atoms with the proviso that the alkylene oxide (2) does not contain in excess of ten carbon atoms, to form a hydrophobic base, said hydrophobic base then being reacted with ethylene oxide to provide said polyoxyalkylene alcohol.
Claim 40
Dependent Claim
29 words
The composition of claim 1 wherein component (II) is a polyoxyalkylene alcohol of up to about 150 oxyalkylene groups, the alkylene radical containing from 2 to 8 carbon atoms.
Claim 41
Dependent Claim
44 words
The composition of claim 1 wherein component (II) is represented by the formula ##STR25## wherein R A and R B are independently alkylene radicals of 2 to 8 carbon atoms, R C is aryl, lower alkyl or arylalkyl, and p is zero to eight.
Claim 42
Dependent Claim
18 words
The composition of claim 1 wherein component (II) is a monohydroxy aromatic compound or a polyhydroxy aromatic compound.
Claim 43
Dependent Claim
44 words
The composition of claim 1 wherein component (II) is a hydroxy-substituted primary amine of the formula ##STR26## wherein R a is a monovalent organic radical containing at least one hydroxy group, the total number of carbon atoms in R a not exceeding about 20.
Claim 44
Dependent Claim
19 words
The composition of claim 42 wherein the total number of carbon atoms in R a does not exceed 10.
Claim 45
Dependent Claim
15 words
The composition of claim 42 wherein R a is a mono- or polyhydroxy-substituted alkyl group.
Claim 46
Dependent Claim
92 words
The composition of claim 1 wherein component (II) is selected from the group consisting of (a) primary, secondary and tertiary alkanol amines which can be represented correspondingly by the formulae: ##STR27## (b) hydroxyl-substituted oxyalkylene analogs of said alkanol amines represented by the formulae: ##STR28## wherein each R is independently, a hydrocarbyl group of one to about 8 carbon atoms or hydroxyl-substituted hydrocarbyl group of 2 to about 8 carbon atoms and R' is a divalent hydrocarbyl group of two to about 18 carbon atoms, and (c) mixtures of two or more thereof.
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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) | 1987-12-18 | 1988-06-18 | 1988-12-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-12-18 | 1992-06-18 | 1992-12-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-12-18 | 1996-06-18 | 1996-12-18 | $7700.00 | Window Closed / Lapsed |