US3941817A
Expired / Lapsed
US
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Tertiary amide amphoteric surface active agents and process for their manufacture
Assignee: ISP Investments LLC
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Filing: 1974-09-03
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Granted: 1976-03-02
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Expires: 1994-09-03
Abstract
Abstract Improved amphoteric surface active agents are obtained from tertiary amides that have been formed by condensation of esters of fatty acids with an aminoalkyl alkanolamine, e.g., aminoethyl ethanolamine, under special conditions, by conventional carboxymethylation with ClCH 2 CO 2 Na or ClCH 2 CO 2 H. The resultant amphoteric surface active agents are especially useful as wetting agents, forming agents, emulsifiers, etc., and in the manufacture of improved shampoos.
Inventors
- 👤 Paritosh Mohan Chakrabarti
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 14:55
CPC Classifications
A; A61; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/40; A61K8/44; A61K47/00; A61K47/06; A61K47/16; A61K47/18; A61K47/183; A61K9/00; A61K9/0012; A61K9/0014; A61Q; A61Q5/00; A61Q5/02; Y; Y10; Y10S; Y10S516/00; Y10S516/01; Y10S516/06
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
93 words
A tertiary amide of the formula ##EQU8## wherein: R 1 is selected from the group consisting of unsubstituted C 5 -C 29 and substituted C 5 -C 29 aliphatic hydrocarbon radicals, which, when substituted, have one or more substituents selected from the group consisting of Cl, Br, OH and OCH 3 ; and R 2 -R 5 are each selected from the group consisting of hydrogen unsubstituted C 2 -C 4 aliphatic hydrocarbon radicals, and substituted C 2 -C 4 aliphatic hydrocarbon radicals whose substituents are as previously defined for R 1 .
Claim 2
Dependent Claim
93 words
A tertiary amide of the formula ##EQU8## wherein: R 1 is selected from the group consisting of unsubstituted C 5 -C 29 and substituted C 5 -C 29 aliphatic hydrocarbon radicals, which, when substituted, have one or more substituents selected from the group consisting of Cl, Br, OH and OCH 3 ; and R 2 -R 5 are each selected from the group consisting of hydrogen unsubstituted C 2 -C 4 aliphatic hydrocarbon radicals, and substituted C 2 -C 4 aliphatic hydrocarbon radicals whose substituents are as previously defined for R 1 .
Claim 3
Dependent Claim
14 words
Amides of claim 1 in which the acyl radical ##EQU9## is derived from tallow.
Claim 4
Dependent Claim
14 words
Amides of claim 1 in which the acyl radical ##EQU10## is a stearyl radical.
Claim 5
Dependent Claim
16 words
Amides of claim 1 in which the acyl radical ##EQU11## is derived from coconut vegetable oil.
Claim 6
Dependent Claim
98 words
A process for making tertiary amides of the formula as defined in claim 1, which comprises condensing a fatty acid ester having the acyl radical ##EQU12## and from 6 to 30 carbon atoms with a hydroxy diamine of the formula: ##EQU13## wherein: R 2 -R 5 are as defined in claim 1, for from 5 minutes to an hour in the presence of a base catalyst and at a temperature between 60° and 120°C until the formation of the tertiary amide; and recovering the tertiary amide formed with the acyl radical ##EQU14## derived from said fatty acid ester.
Claim 7
Dependent Claim
13 words
The process of claim 5 in which said ester is the methyl ester.
Claim 8
Dependent Claim
12 words
The process of claim 5 in which said ester is a triglyceride.
Claim 9
Dependent Claim
13 words
The process of claim 5 in which said base catalyst is sodium methoxide.
Claim 10
Dependent Claim
26 words
The process of claim 6 in which methanol formed during the condensation of said ester and said hydroxy diamine is removed as said methanol is formed.
Claim 11
Dependent Claim
25 words
The process of claim 7 in which glycerol formed during condensation of said ester and said hydroxy diamine is left with the reaction product amide.
Claim 12
Dependent Claim
113 words
Amphoteric surface active agents of the formula: ##EQU15## wherein R 1 is selected from the group consisting of unsubstituted c 5 -C 29 and substituted C 5 -C 29 aliphatic hydrocarbon radicals, which, when substituted, have one or more substituents selected from the group consisting of Cl, Br, OH and OCH 3 ; and R 2 -R 5 are each selected from the group consisting of hydrogen, unsubstituted C 2 -C 4 aliphatic hydrocarbon radicals, and substituted C 2 -C 4 aliphatic hydrocarbon radicals whose substituents are as previously defined for R 1 ; and wherein M is selected from the group consisting of hydrogen, an alkali metal cation, and an ammonium cation.
Claim 13
Dependent Claim
113 words
Amphoteric surface active agents of the formula: ##EQU15## wherein R 1 is selected from the group consisting of unsubstituted c 5 -C 29 and substituted C 5 -C 29 aliphatic hydrocarbon radicals, which, when substituted, have one or more substituents selected from the group consisting of Cl, Br, OH and OCH 3 ; and R 2 -R 5 are each selected from the group consisting of hydrogen, unsubstituted C 2 -C 4 aliphatic hydrocarbon radicals, and substituted C 2 -C 4 aliphatic hydrocarbon radicals whose substituents are as previously defined for R 1 ; and wherein M is selected from the group consisting of hydrogen, an alkali metal cation, and an ammonium cation.
Claim 14
Dependent Claim
25 words
An amphoteric surface active agent according to claim 11 having the formula: ##EQU16## wherein the acyl radical R 1 CO is derived from hydrogenated tallow.
Claim 15
Dependent Claim
119 words
A process for making tertiary amide amphoteric surfactants of the formula defined in claim 11, which comprises condensing a fatty acid ester having from 6 to 30 carbon atoms with a hydroxy diamine of the formula: ##EQU17## wherein: R 2 -R 5 are as defined in claim 1, for from 5 minutes to an hour in the presence of a base catalyst and at a temperature between 60° and 120°C, until formation of the tertiary amide, and reacting the reaction product containing said amide with an acidic material selected from the group consisting of ##EQU18## and salts thereof wherein R 6 is selected from the group consisting of hydrogen and C 1 -C 4 alkyl to form said surfactants.
Claim 16
Dependent Claim
18 words
The process of claim 13 in which said fatty acid ester is an ester of a lower alcohol.
Claim 17
Dependent Claim
13 words
The process of claim 14 in which said ester is the methyl ester.
Claim 18
Dependent Claim
12 words
The process of claim 13 in which said ester is a triglyceride.
Claim 19
Dependent Claim
13 words
The process of claim 13 in which said base catalyst is sodium methoxide.
Claim 20
Dependent Claim
26 words
The process of claim 15 in which methanol formed during the condensation of said ester and said hydroxy diamine is removed as said methanol is formed.
Claim 21
Dependent Claim
25 words
The process of claim 16 in which glycerol formed during condensation of said ester and said hydroxy diamine is left with the reaction product amide.
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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) | 1979-03-02 | 1979-09-01 | 1980-03-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-03-02 | 1983-09-01 | 1984-03-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-03-02 | 1987-09-01 | 1988-03-02 | $7700.00 | Window Closed / Lapsed |