US4304932A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for producing novel carboalkylated surface active agents and product
Assignee: Solvay Solutions UK Ltd
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Filing: 1980-03-10
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Granted: 1981-12-08
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Expires: 2000-03-10
Abstract
Abstract The reaction of an imidazoline base of the formula: ##STR1## wherein R represents an aliphatic group comprising from 6 to 22 carbon atoms and R 1 represents a substituted or unsubstituted alkyl or alkenyl group comprising 1 to 4 carbon atoms, with a carbo-alkylating agent is carried out in two stages. Initially the pH is maintained in the range 7 to 11 and subsequently it is maintained in the range 9 to 12.5. These conditions encourage at least part of the imidazoline to undergo alkylation followed by hydrolysis and further alkylation. The di alkylated amidoamines thus produced are believed to be novel. The reaction products are surfactants which exhibit very low skin irritancy and have a desirably low viscosity. They find particular application in shampoo formulations.
Inventors
- 👤 Brinley M. Phillips
- 👤 Maurice E. Thompson
- 👤 Alan J. Lambie
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 07:21
CPC Classifications
A; A61; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/49; A61K8/494; A61K8/4946; A61Q; A61Q19/00; A61Q19/10; A61Q5/00; A61Q5/02
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
224 words
A process for the preparation of a surface active agent comprising a mixture containing mono- and dicarbo-alkylated derivatives of acylated ethylene diamines which comprises treating an imidazoline of the formula ##STR8## wherein R represents an aliphatic group comprising from 6 to 22 carbon atoms and R 1 represents a substituted or unsubstituted alkyl or alkenyl group having from 1 to 4 carbon atoms with from 1 to 4 moles per mole of imidazoline of a carboalkylating agent of the formula Z-R 2 -COO - wherein R 2 represents a substituted or unsubstituted alkylene group having from 1 to 4 carbon atoms and Z represents a halogen atom characterized in that the reaction is carried out at a temperature of from 40° to 90° C., the pH of the reaction medium being maintained in the range 7.0 to 11.5 and after at least 0.5 mole of carbo-alkylating agent per mole of imidazoline have reacted the pH of the reaction medium is maintained in the range of more than 9 up to 12.0 to produce said mixture; said mixture having a ratio of said mono- to said di-carbo-alkylated derivatives in the range of from 1:2.0 to 1:0.2 (all pH's being expressed as the pH of a sample of the reaction medium diluted with deionized water so as to bring the solid contents thereof to substantially 10%).
Claim 2
Dependent Claim
224 words
A process for the preparation of a surface active agent comprising a mixture containing mono- and dicarbo-alkylated derivatives of acylated ethylene diamines which comprises treating an imidazoline of the formula ##STR8## wherein R represents an aliphatic group comprising from 6 to 22 carbon atoms and R 1 represents a substituted or unsubstituted alkyl or alkenyl group having from 1 to 4 carbon atoms with from 1 to 4 moles per mole of imidazoline of a carboalkylating agent of the formula Z-R 2 -COO - wherein R 2 represents a substituted or unsubstituted alkylene group having from 1 to 4 carbon atoms and Z represents a halogen atom characterized in that the reaction is carried out at a temperature of from 40° to 90° C., the pH of the reaction medium being maintained in the range 7.0 to 11.5 and after at least 0.5 mole of carbo-alkylating agent per mole of imidazoline have reacted the pH of the reaction medium is maintained in the range of more than 9 up to 12.0 to produce said mixture; said mixture having a ratio of said mono- to said di-carbo-alkylated derivatives in the range of from 1:2.0 to 1:0.2 (all pH's being expressed as the pH of a sample of the reaction medium diluted with deionized water so as to bring the solid contents thereof to substantially 10%).
Claim 3
Dependent Claim
23 words
A process according to claim 1 wherein R 1 represents a hydroxy-alkyl or amino alkyl group having from 1 to 4 carbon atoms.
Claim 4
Dependent Claim
14 words
A process according to claim 2 wherein R 1 represents a hydroxy ethane group.
Claim 5
Dependent Claim
20 words
A process according to claim 1 wherein the group R comprises an average of from 10 to 18 carbon atoms.
Claim 6
Dependent Claim
20 words
A process according to claim 2 wherein the group R comprises an average of from 12 to 14 carbon atoms.
Claim 7
Dependent Claim
15 words
A process according to claim 2 wherein R 2 represents an ethylene or methylene group.
Claim 8
Dependent Claim
18 words
A process according to claim 2 characterized in that the carbo-alkylating agent has the formula Cl-CH 2 -COO--.
Claim 9
Dependent Claim
42 words
A process according to claim 1 wherein the pH of the reaction medium is maintained at or below a value given by the equation pH max=(200-temperature in °C.)/13 until at least 0.5 moles of carbo-alkylating agent per mole of imidazoline have reacted.
Claim 10
Dependent Claim
42 words
A process according to claim 6 wherein the pH of the reaction medium is maintained at or below a value given by the equation pH max=(200-temperature in °C.)/13 until at least 0.5 moles of carbo-alkylating agent per mole of imidazoline have reacted.
Claim 11
Dependent Claim
36 words
A process according to claim 1 wherein the temperature of the reaction medium is maintained in the range 50° to 70° C. until at least 0.5 moles of carbo-alkylating agent per mole of imidazoline have reacted.
Claim 12
Dependent Claim
36 words
A process according to claim 8 wherein the temperature of the reaction medium is maintained in the range 50° to 70° C. until at least 0.5 moles of carbo-alkylating agent per mole of imidazoline have reacted.
Claim 13
Dependent Claim
35 words
A process according to claim 1 wherein the pH of the reaction medium is maintained in the range 9.0 to 10.5 until at least 0.5 moles of carbo-alkylating agent per mole of imidazoline have reacted.
Claim 14
Dependent Claim
35 words
A process according to claim 9 wherein the pH of the reaction medium is maintained in the range 9.0 to 10.5 until at least 0.5 moles of carbo-alkylating agent per mole of imidazoline have reacted.
Claim 15
Dependent Claim
35 words
A process according to claim 1 wherein after 0.5 moles of carbo-alkylating agent per mole of imidazoline have reacted the pH of the reaction medium is maintained at a value of from 10.5 to 12.0.
Claim 16
Dependent Claim
29 words
A process according to claim 14 wherein after 0.7 moles of carbo-alkylating agent per mole of imidazoline have reacted the pH is maintained in the range 10.5 to 12.0.
Claim 17
Dependent Claim
35 words
A process according to claim 13 wherein after 0.5 moles of carbo-alkylating agent per mole of imidazoline have reacted the pH of the reaction medium is maintained at a value of from 10.5 to 12.0.
Claim 18
Dependent Claim
32 words
A process according to claim 1 wherein after 0.5 moles of carbo-alkylating agent per mole of imidazoline have reacted the temperature of the reaction medium is maintained in the range 60°-80° C.
Claim 19
Dependent Claim
32 words
A process according to claim 9 wherein after 0.5 moles of carbo-alkylating agent per mole of imidazoline have reacted the temperature of the reaction medium is maintained in the range 60°-80° C.
Claim 20
Dependent Claim
32 words
The surface active agent produced by the process according to any of claims 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18.
Claim 21
Dependent Claim
16 words
A composition according to claim 19 which comprises less than 20% by weight of non-carbo-alkylated material.
Claim 22
Dependent Claim
23 words
A composition according to claim 20 wherein the ratio of mono carbo-alkylated species to dicarbo-alkylated species is in the range 1:1.3 to 1:0.4.
Claim 23
Dependent Claim
45 words
A composition according to claim 21 wherein R 1 is a hydroxy-alkyl or amino alkyl group containing from 1 to 4 carbon atoms; the R group contains an average of from 10 to 18 carbon atoms; and R 2 is an ethylene or methylene group.
Claim 24
Dependent Claim
31 words
A composition according to claim 21 wherein the group R contains an average of from 12 to 14 carbon atoms; and wherein the carbo-alkylating agent has the formula Cl--CH 2 --COO--.
Claim 25
Dependent Claim
14 words
A composition according to claim 23 wherein R 1 is a hydroxy ethane group.
Claim 26
Dependent Claim
218 words
A surface active agent comprising a mixture containing mono- and di-carbo-alkylated derivatives of acylated ethylene diamines produced by the process which comprises treating an imidazoline of the formula ##STR9## wherein R represents an aliphatic group comprising from 6 to 22 carbon atoms and R 1 represents a substituted or unsubstituted alkyl or alkenyl group having from 1 to 4 carbon atoms with from 1 to 4 moles per mole of imidazoline of a carboalkylating agent of the formula Z-R 2 -COO - wherein R 2 represents a substituted or unsubstituted alkylene group having from 1 to 4 carbon atoms and Z represents a halogen atom characterized in that the reaction is carried out at a temperature of from 40° to 90° C., the pH of the reaction medium being maintained in the range 7.0 to 11.5 and after at least 0.5 mole of carbo-alkylating agent per mole of imidazoline have reacted the pH of the reaction medium is maintained in the range 9.0 to 12.0 to produce said mixture; said mixture having a ratio of said mono- to said di-carbo-alkylated derivatives in the range of from 1:2.0 to 1:0.2 (all pH's being expressed as the pH of a sample of the reaction medium diluted with deionized water so as to bring the solid contents thereof to substantially 10%).
Claim 27
Dependent Claim
218 words
A surface active agent comprising a mixture containing mono- and di-carbo-alkylated derivatives of acylated ethylene diamines produced by the process which comprises treating an imidazoline of the formula ##STR9## wherein R represents an aliphatic group comprising from 6 to 22 carbon atoms and R 1 represents a substituted or unsubstituted alkyl or alkenyl group having from 1 to 4 carbon atoms with from 1 to 4 moles per mole of imidazoline of a carboalkylating agent of the formula Z-R 2 -COO - wherein R 2 represents a substituted or unsubstituted alkylene group having from 1 to 4 carbon atoms and Z represents a halogen atom characterized in that the reaction is carried out at a temperature of from 40° to 90° C., the pH of the reaction medium being maintained in the range 7.0 to 11.5 and after at least 0.5 mole of carbo-alkylating agent per mole of imidazoline have reacted the pH of the reaction medium is maintained in the range 9.0 to 12.0 to produce said mixture; said mixture having a ratio of said mono- to said di-carbo-alkylated derivatives in the range of from 1:2.0 to 1:0.2 (all pH's being expressed as the pH of a sample of the reaction medium diluted with deionized water so as to bring the solid contents thereof to substantially 10%).
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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) | 1984-12-07 | 1985-06-08 | 1985-12-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-12-07 | 1989-06-08 | 1989-12-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-12-07 | 1993-06-08 | 1993-12-08 | $7700.00 | Window Closed / Lapsed |