US4251380A
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US
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Quaternary ammonium diester salt composition and hydrocarbon oil containing same
Assignee: Afton Chemical Additives Corp
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Filing: 1979-06-28
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Granted: 1981-02-17
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Expires: 1999-06-28
Abstract
Abstract A quaternary ammonium salt of a diester represented by the formula: <IMAGE> in which Ri, Rii, Riii and Riv represent hydrogen, alkyl or alkenyl radicals at least one of which is a hydrocarbyl radical having from 50-200 carbon atoms, R is a divalent radical having from 2-10 carbon, or carbon and oxygen atoms, Rv is hydrogen or a hydrocarbyl radical, z has a value from 0-4 and X is an anion is provided, as well as a method of preparation and a hydrocarbon lubricating oil composition containing same.
Inventors
- 👤 Kenneth G. Hammond
- 👤 Harry Chafetz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 23:09
CPC Classifications
C; C08; C08F; C08F8/00; C08F8/44; C10; C10M; C10M2205/00; C10M2209/00; C10M2209/10; C10M2209/103; C10M2209/104; C10M2209/109; C10M2215/00; C10M2215/02; C10M2215/06; C10M2215/064; C10M2217/00; C10M2217/02; C10M2217/04; C10M2219/00; C10M2219/04; C10M2219/046; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/045; C10N; C10N2010/00; C10N2010/04
Claims Analysis
Total Claims: 38
Claim 1
Independent Claim
92 words
A quaternary ammonium diester salt composition represented by the formula: ##STR8## in which R i , R ii , R iii and R iv represent hydrogen, alkyl or alkenyl hydrocarbyl radicals at least one of which is a hydrocarbyl radical having from 50-200 carbon atoms, R is a divalent radical having from 2-10 carbon, or carbon and oxygen atoms, R v is hydrogen or a hydrocarbyl radical, z has a value from 0-4 and X is an anion selected from the group consisting of halides, sulfates, carbonates, sulfites, borates, carboxylates, and phosphates.
Claim 2
Dependent Claim
92 words
A quaternary ammonium diester salt composition represented by the formula: ##STR8## in which R i , R ii , R iii and R iv represent hydrogen, alkyl or alkenyl hydrocarbyl radicals at least one of which is a hydrocarbyl radical having from 50-200 carbon atoms, R is a divalent radical having from 2-10 carbon, or carbon and oxygen atoms, R v is hydrogen or a hydrocarbyl radical, z has a value from 0-4 and X is an anion selected from the group consisting of halides, sulfates, carbonates, sulfites, borates, carboxylates, and phosphates.
Claim 3
Dependent Claim
40 words
A quaternary ammonium diester salt according to claim 1 in which R is a divalent hydrocarbon radical having from 2 to 6 carbon atoms and R v is hydrogen or an alkyl radical having from 1 to 3 carbon atoms.
Claim 4
Dependent Claim
34 words
A quaternary ammonium diester salt according to claim 1 in which the hydrocarbyl radical represented by R i , R ii , R iii or R iv has from 75 to 150 carbon atoms.
Claim 5
Dependent Claim
16 words
A quaternary ammonium salt according to claim 1 in which said anion is the chloride ion.
Claim 6
Dependent Claim
16 words
A quaternary ammonium salt according to claim 1 in which said anion is the sulfate ion.
Claim 7
Dependent Claim
16 words
A quaternary ammonium salt according to claim 1 in which said anion is a borate ion.
Claim 8
Dependent Claim
93 words
A quaternary ammonium diester salt composition represented by the formula: ##STR9## in which R i represents a hydrocarbyl radical having from 50 to 200 carbon atoms, R ii , R iii and R iv represent hydrogen or methyl radicals, R is a divalent hydrocarbon radical having from 2 to 6 carbon atoms, X is an anion selected from the group consisting of chloride, bromide, sulfate and borate ions, R v is hydrogen or an aliphatic hydrocarbon radical having from 1 to 3 carbon atoms and z has a value from 0 to 2.
Claim 9
Dependent Claim
93 words
A quaternary ammonium diester salt composition represented by the formula: ##STR9## in which R i represents a hydrocarbyl radical having from 50 to 200 carbon atoms, R ii , R iii and R iv represent hydrogen or methyl radicals, R is a divalent hydrocarbon radical having from 2 to 6 carbon atoms, X is an anion selected from the group consisting of chloride, bromide, sulfate and borate ions, R v is hydrogen or an aliphatic hydrocarbon radical having from 1 to 3 carbon atoms and z has a value from 0 to 2.
Claim 10
Dependent Claim
25 words
A quaternary ammonium diester salt according to claim 7 in which the hydrocarbyl radical represented by R i has from 75 to 150 carbon atoms.
Claim 11
Dependent Claim
22 words
A quaternary ammonium diester salt according to claim 8 in which the hydrocarbyl radical represented by R i is a polyisobutenyl radical.
Claim 12
Dependent Claim
33 words
A quaternary ammonium diester salt according to claim 7 in which R is a divalent hydrocarbon radical having from 2 to 4 carbon atoms and R v is hydrogen or a methyl radical.
Claim 13
Dependent Claim
16 words
A quaternary ammonium salt according to claim 7 in which said anion is the chloride ion.
Claim 14
Dependent Claim
16 words
A quaternary ammonium salt according to claim 7 in which said anion is a borate ion.
Claim 15
Dependent Claim
113 words
A lubricating oil composition comprising a major portion of a mineral lubricating oil and a minor dispersant amount of a quaternary ammonium diester salt composition represented by the formula: ##STR10## in which R i , R ii . R iii and R iv represent hydrogen, alkyl or alkenyl hydrocarbyl radicals at least one of which is a hydrocarbyl radical having from 50-200 carbon atoms, R is a divalent radical having from 2-10 carbon, or carbon and oxygen atoms, R v is hydrogen or a hydrobarbyl radical, z has a value from 0 to 4, and X is an anion selected from the group consisting of halides, sulfates, carbonates, sulfites, borates, carboxylates, and phosphates.
Claim 16
Dependent Claim
113 words
A lubricating oil composition comprising a major portion of a mineral lubricating oil and a minor dispersant amount of a quaternary ammonium diester salt composition represented by the formula: ##STR10## in which R i , R ii . R iii and R iv represent hydrogen, alkyl or alkenyl hydrocarbyl radicals at least one of which is a hydrocarbyl radical having from 50-200 carbon atoms, R is a divalent radical having from 2-10 carbon, or carbon and oxygen atoms, R v is hydrogen or a hydrobarbyl radical, z has a value from 0 to 4, and X is an anion selected from the group consisting of halides, sulfates, carbonates, sulfites, borates, carboxylates, and phosphates.
Claim 17
Dependent Claim
45 words
A lubricating oil composition according to claim 13 having a quaternary ammonium diester salt in which R is a divalent hydrocarbon radical having from 2 to 6 carbon atoms and R v is hydrogen or an alkyl radical having from 1 to 3 carbon atoms.
Claim 18
Dependent Claim
30 words
A lubricating oil composition according to claim 13 having a quaternary ammonium diester salt in which the hydrocarbyl radical represented by R i has from 75 to 150 carbon atoms.
Claim 19
Dependent Claim
22 words
A lubricating oil composition according to claim 13 having a quaternary ammonium diester salt in which said anion is the chloride ion.
Claim 20
Dependent Claim
22 words
A lubricating oil composition according to claim 13 having a quaternary ammonium diester salt in which said anion is the sulfate ion.
Claim 21
Dependent Claim
22 words
A lubricating oil composition according to claim 13 having a quaternary ammonium diester salt in which said anion is a borate ion.
Claim 22
Dependent Claim
112 words
A lubricating oil composition comprising a major portion of a mineral lubricating oil and a minor dispersant amount of a quaternary ammonium diester salt, composition represented by the formula: ##STR11## in which R i represents a hydrocarbyl radical having from 50 to 200 carbon atoms, R ii , R iii and R iv represent hydrogen or methyl radicals, R is a divalent hydrocarbon radical having from 2 to 6 carbon atoms, X is an anion selected from the group consisting of chloride, bromide, sulfate and borate ions, R v is hydrogen or an aliphatic hydrocarbon radical having from 1 to 3 carbon atoms and z has a value from 0 to 2.
Claim 23
Dependent Claim
112 words
A lubricating oil composition comprising a major portion of a mineral lubricating oil and a minor dispersant amount of a quaternary ammonium diester salt, composition represented by the formula: ##STR11## in which R i represents a hydrocarbyl radical having from 50 to 200 carbon atoms, R ii , R iii and R iv represent hydrogen or methyl radicals, R is a divalent hydrocarbon radical having from 2 to 6 carbon atoms, X is an anion selected from the group consisting of chloride, bromide, sulfate and borate ions, R v is hydrogen or an aliphatic hydrocarbon radical having from 1 to 3 carbon atoms and z has a value from 0 to 2.
Claim 24
Dependent Claim
30 words
A lubricating oil composition according to claim 19 having a quaternary ammonium diester salt in which the hydrocarbyl radical represented by R i has from 75 to 150 carbon atoms.
Claim 25
Dependent Claim
27 words
A lubricating oil composition according to claim 19 having a quaternary ammonium diester salt in which the hydrocarbyl radical represented by R i is a polyisobutenyl radical.
Claim 26
Dependent Claim
45 words
A lubricating oil composition according to claim 19 having a quaternary ammonium diester salt in which R is a divalent hydrocarbon radical having from 2 to 6 carbon atoms and R v is hydrogen or an alkyl radical having from 1 to 3 carbon atoms.
Claim 27
Dependent Claim
21 words
A lubricating oil composition according to claim 19 having a quaternary ammonium salt in which said anion is the chloride ion.
Claim 28
Dependent Claim
21 words
A lubricating oil composition according to claim 19 having a quaternary ammonium salt in which said anion is a borate ion.
Claim 29
Independent Claim
155 words
A method for preparing a quaternary ammonium diester salt composition which comprises reacting a polyolefin having from about 50 to 200 carbon atoms, with maleic anhydride in the presence of a brominated compound to produce an alkenylsuccinic acid anhydride in which said alkenyl radical has from about 50 to 200 carbon atoms reacting said alkenylsuccinic acid anhydride with a haloalcohol represented by the formula X--R--OH in which R is a divalent radical having from 2 to 10 carbon, or carbon and oxygen atoms in the presence of an acid reacting catalyst employing a mole ratio of 2 to 10 moles of said haloalcohol per mole of said anhydride to produce an intermediate diester product and reacting said intermediate diester product with a tertiary amine represented by the formula: ##STR12## in which R v is hydrogen or a hydrocarbyl radical having from 1 to 3 carbon atoms and z has a value from 0 to 4.
Claim 30
Independent Claim
155 words
A method for preparing a quaternary ammonium diester salt composition which comprises reacting a polyolefin having from about 50 to 200 carbon atoms, with maleic anhydride in the presence of a brominated compound to produce an alkenylsuccinic acid anhydride in which said alkenyl radical has from about 50 to 200 carbon atoms reacting said alkenylsuccinic acid anhydride with a haloalcohol represented by the formula X--R--OH in which R is a divalent radical having from 2 to 10 carbon, or carbon and oxygen atoms in the presence of an acid reacting catalyst employing a mole ratio of 2 to 10 moles of said haloalcohol per mole of said anhydride to produce an intermediate diester product and reacting said intermediate diester product with a tertiary amine represented by the formula: ##STR12## in which R v is hydrogen or a hydrocarbyl radical having from 1 to 3 carbon atoms and z has a value from 0 to 4.
Claim 31
Dependent Claim
19 words
A method according to claim 25 in which said alkenyl radical has from about 75 to 150 carbon atoms.
Claim 32
Dependent Claim
18 words
A method according to claim 25 in which said haloalcohol is 2-chloroethanol and said tertiary amine is 4-picoline.
Claim 33
Dependent Claim
18 words
A method according to claim 25 in which said haloalcohol is 4-chlorobutanol and said tertiary amine is 4-picoline.
Claim 34
Dependent Claim
15 words
A method according to claim 25 in which said acid reacting catalyst is sulfuric acid.
Claim 35
Dependent Claim
22 words
A method according to claim 25 in which the mole ratio of said haloalcohol to said anhydride is from 2 to 2.5.
Claim 36
Dependent Claim
38 words
A method according to claim 25 in which said quaternary ammonium diester salt is further reacted with an acid selected from the group consisting of sulfuric acid, carbonic acid, sulfurous acid, boric acid, carboxylic acids and phosphoric acid.
Claim 37
Dependent Claim
20 words
A method according to claim 25 in which said brominated compound is a brominated hydantoin, brominated phenol or brominated alkanol.
Claim 38
Dependent Claim
32 words
A method according to claim 25 in which the reaction of the intermediate diester with the tertiary amine is conducted in the presence of a small amount of boric acid and/or base.
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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) | 1984-02-17 | 1984-08-18 | 1985-02-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-02-17 | 1988-08-18 | 1989-02-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-02-17 | 1992-08-18 | 1993-02-17 | $7700.00 | Window Closed / Lapsed |