US4142980A
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Mannich reaction products made with alkyphenol substituted aliphatic unsaturated carboxylic acids
Assignee: Ethyl Corp
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Filing: 1977-09-09
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Granted: 1979-03-06
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Expires: 1997-09-09
Abstract
Abstract Disclosed are processes for making certain compositions, the compositions and lubricating oils containing certain compositions. Disclosed are a substituted phenol comprising the reaction product of an alkyl phenol, said alkyl substituent containing about 50 to about 20,000 carbon atoms, and an aliphatic unsaturated carboxylic acid containing about 3 to about 100 carbon atoms; and a process for the manufacture of said substituted phenol. Also disclosed are oil soluble Mannich reaction products of said substituted phenol, an amine having at least one reactive nitrogen, and a formaldehyde affording reactant; and a process for the manufacture of said Mannich product. Also disclosed is a lubricating oil composition containing said Mannich reaction product.
Inventors
- 👤 Robert E. Karll
- 👤 Richard J. Lee
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 21:30
CPC Classifications
C; C10; C10M; C10M159/00; C10M159/12; C10M159/16; C08; C08F; C08F8/00; C08F8/14; C08F8/30; C08F8/32; C08F8/44; C08F2810/00; C08F2810/20; C08F2810/30; C10M2215/00; C10M2215/02; C10M2215/04; C10M2215/042; C10M2215/24; C10M2215/26; C10M2217/00; C10M2217/04; C10M2217/046; C10M2217/06
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
100 words
An oil soluble Mannich reaction product of: (a) the reaction product of an alkyl phenol, said alkyl substituent containing about 50 to about 20,000 carbon atoms, and an aliphatic unsaturated carboxylic acid containing about 3 to about 100 carbon atoms; (b) an amine having at least one reactive nitrogen and containing less than about 100 carbon atoms and having the general formula: ##STR5## wherein A is a divalent alkylene radical of 2 to 6 carbon atoms and x is an integer of 1 to 10; and (c) a formaldehyde affording reactant wherein the molar ratio of a:b:c is about 1:0.7-1.0:1.5-2.
Claim 2
Dependent Claim
100 words
An oil soluble Mannich reaction product of: (a) the reaction product of an alkyl phenol, said alkyl substituent containing about 50 to about 20,000 carbon atoms, and an aliphatic unsaturated carboxylic acid containing about 3 to about 100 carbon atoms; (b) an amine having at least one reactive nitrogen and containing less than about 100 carbon atoms and having the general formula: ##STR5## wherein A is a divalent alkylene radical of 2 to 6 carbon atoms and x is an integer of 1 to 10; and (c) a formaldehyde affording reactant wherein the molar ratio of a:b:c is about 1:0.7-1.0:1.5-2.
Claim 3
Dependent Claim
16 words
The Mannich reaction product of claim 1 wherein the molar ratio of a:b:c is about 1:1:1.5.
Claim 4
Dependent Claim
24 words
The Mannich reaction product of claim 1 wherein the reaction product is formed at a temperature from about 100° F. to about 350° F.
Claim 5
Dependent Claim
40 words
The Mannich reaction product of claim 1 wherein the substituted phenol comprises a para substituted alkylphenol wherein said alkyl group contains about 200 to about 300 carbon atoms and said carboxylic acid contains about 6 to about 40 carbon atoms.
Claim 6
Dependent Claim
14 words
The Mannich reaction product of claim 1 wherein the formaldehyde affording reactant is formaldehyde.
Claim 7
Dependent Claim
16 words
The Mannich reaction product of claim 5 where the molar ratio of a:b:c is about 1:1:1.5.
Claim 8
Dependent Claim
29 words
The Mannich reaction product of claim 6 wherein A is a divalent alkylene radical of 2 to 3 carbon atoms and x is an integer of 2 to 6.
Claim 9
Dependent Claim
13 words
The Mannich reaction product of claim 7 wherein the amine comprises tetraethylene pentamine.
Claim 10
Dependent Claim
25 words
The Mannich reaction product of claim 8 wherein the reaction product is formed at a temperature of from about 100° F. to about 350° F.
Claim 11
Dependent Claim
131 words
A process for the manufacture of an oil soluble Mannich reaction product comprising: first reacting an alkyl phenol, said alkyl substituent containing about 50 to about 20,000 carbon atoms, with an aliphatic unsaturated carboxylic acid containing about 3 to about 100 carbon atoms to form a first reaction product; and then reacting the first reaction product with an amine having at least one reactive nitrogen and containing less than about 100 carbon atoms wherein the amine comprises an amine having the general formula: ##STR6## wherein A is a divalent alkylene radical of 2 to 6 carbon atoms and x is an integer of 1 to 10; and a formaldehyde affording reactant, wherein the molar ratio of the first reaction product:amine:formaldehyde affording reactant is about 1:0.7-1.0:1.5-2, thereby forming a Mannich reaction product.
Claim 12
Dependent Claim
131 words
A process for the manufacture of an oil soluble Mannich reaction product comprising: first reacting an alkyl phenol, said alkyl substituent containing about 50 to about 20,000 carbon atoms, with an aliphatic unsaturated carboxylic acid containing about 3 to about 100 carbon atoms to form a first reaction product; and then reacting the first reaction product with an amine having at least one reactive nitrogen and containing less than about 100 carbon atoms wherein the amine comprises an amine having the general formula: ##STR6## wherein A is a divalent alkylene radical of 2 to 6 carbon atoms and x is an integer of 1 to 10; and a formaldehyde affording reactant, wherein the molar ratio of the first reaction product:amine:formaldehyde affording reactant is about 1:0.7-1.0:1.5-2, thereby forming a Mannich reaction product.
Claim 13
Dependent Claim
19 words
The process of claim 10 wherein the molar ratio of the first reaction product:amine:formaldehyde affording reactant is about 1:1:1.5.
Claim 14
Dependent Claim
41 words
The process of claim 10 wherein the first reaction product is formed at a temperature from about 80° F. to about 250° F. and the Mannich reaction product is formed at a temperature from about 200° F. to about 350° F.
Claim 15
Dependent Claim
38 words
The process of claim 10 wherein the substituted phenol comprises a para substituted alkylphenol wherein said alkyl group contains about 200 to about 300 carbon atoms and said carboxylic acid contains about 6 to about 40 carbon atoms.
Claim 16
Dependent Claim
11 words
The process of claim 13 wherein the formaldehyde-affording reactant is formaldehyde.
Claim 17
Dependent Claim
27 words
The process of claim 14 wherein A is a divalent alkylene radical of 2 to 3 carbon atoms and x is an integer of 2 to 6.
Claim 18
Dependent Claim
11 words
The process of claim 15 wherein the amine comprises tetraethylene pentamine.
Claim 19
Dependent Claim
109 words
An oil soluble Mannich reaction product comprising the reaction product of: (a) a disubstituted phenol having the formula: ##STR7## wherein R is an alkyl substituent containing from about 50 to about 20,000 carbon atoms, and n and r are integers such that n + r ≧ 5 ≦ 15; (b) an amine having at least one reactive nitrogen and containing less than about 100 carbon atoms and having the general formula: ##STR8## wherein A is a divalent alkylene radical of 2 to 6 carbon atoms and x is an integer of 1 to 10; and (c) a formaldehyde affording reactant wherein the molar ratio of a:b:c is about 1:0.7-1.0:1.5-2.
Claim 20
Dependent Claim
109 words
An oil soluble Mannich reaction product comprising the reaction product of: (a) a disubstituted phenol having the formula: ##STR7## wherein R is an alkyl substituent containing from about 50 to about 20,000 carbon atoms, and n and r are integers such that n + r ≧ 5 ≦ 15; (b) an amine having at least one reactive nitrogen and containing less than about 100 carbon atoms and having the general formula: ##STR8## wherein A is a divalent alkylene radical of 2 to 6 carbon atoms and x is an integer of 1 to 10; and (c) a formaldehyde affording reactant wherein the molar ratio of a:b:c is about 1:0.7-1.0:1.5-2.
Claim 21
Dependent Claim
16 words
The Mannich reaction product of claim 17 wherein the molar ratio of a:b:c is about 1:1:1.5.
Claim 22
Dependent Claim
40 words
The Mannich reaction product of claim 18 wherein the amine comprises an amine having the general formula: ##STR9## wherein A is a divalent alkylene radical of 2 to 6 carbon atoms and x is an integer of 1 to 10.
Claim 23
Dependent Claim
14 words
The Mannich reaction product of claim 19 wherein the formaldehyde affording reactant is formaldehyde.
Claim 24
Dependent Claim
29 words
The Mannich reaction product of claim 20 wherein A is a divalent alkylene radical of 2 to 3 carbon atoms and x is an integer of 2 to 6.
Claim 25
Dependent Claim
13 words
The Mannich reaction product of claim 21 wherein the amine comprises tetraethylene pentamine.
Claim 26
Dependent Claim
132 words
A lubricating oil composition comprising a major proportion of lubricating oil and a sufficient amount of an oil soluble Mannich reaction product to improve the detergency properties of said lubricating oil, said Mannich reaction product comprising the reaction product of: (a) the reaction product of an alkyl phenol, said alkyl substituent containing about 50 to about 20,000 carbon atoms, and an aliphatic unsaturated carboxylic acid containing about 3 to about 100 carbon atoms; (b) an amine having at least one reactive nitrogen and containing less than about 100 carbon atoms having the general formula: ##STR10## wherein A is a divalent alkylene radical of 2 to 6 carbon atoms and x is an integer of 1 to 10; and (c) a formaldehyde affording reactant wherein the molar ratio of a:b:c is about 1:0.7-1.0:1.5-2.
Claim 27
Dependent Claim
132 words
A lubricating oil composition comprising a major proportion of lubricating oil and a sufficient amount of an oil soluble Mannich reaction product to improve the detergency properties of said lubricating oil, said Mannich reaction product comprising the reaction product of: (a) the reaction product of an alkyl phenol, said alkyl substituent containing about 50 to about 20,000 carbon atoms, and an aliphatic unsaturated carboxylic acid containing about 3 to about 100 carbon atoms; (b) an amine having at least one reactive nitrogen and containing less than about 100 carbon atoms having the general formula: ##STR10## wherein A is a divalent alkylene radical of 2 to 6 carbon atoms and x is an integer of 1 to 10; and (c) a formaldehyde affording reactant wherein the molar ratio of a:b:c is about 1:0.7-1.0:1.5-2.
Claim 28
Dependent Claim
14 words
The composition of claim 23 wherein the molar ratio of a:b:c is about 1:1:1.5.
Claim 29
Dependent Claim
38 words
The composition of claim 23 wherein the substituted phenol comprises a para substituted alkylphenol wherein said alkyl group contains about 200 to about 300 carbon atoms and said carboxylic acid contains about 6 to about 40 carbon atoms.
Claim 30
Dependent Claim
12 words
The composition of claim 25 wherein the formaldehyde affording reactant is formaldehyde.
Claim 31
Dependent Claim
27 words
The composition of claim 26 wherein A is a divalent alkylene radical of 2 to 3 carbon atoms and x is an integer of 2 to 6.
Claim 32
Dependent Claim
11 words
The composition of claim 27 wherein the amine comprises tetraethylene pentamine.
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) | 1982-03-05 | 1982-09-04 | 1983-03-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-03-05 | 1986-09-04 | 1987-03-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-03-05 | 1990-09-04 | 1991-03-06 | $7700.00 | Window Closed / Lapsed |