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US4492802A
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Process for manufacture of quaternary ammonium compounds
Assignee: Henkel AG and Co KGaA
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Filing: 1982-04-19
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Granted: 1985-01-08
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Expires: 2002-04-19
Abstract
Abstract Process for the manufacture of quaternary ammonium compounds by reacting a compound having a terminal epoxide troup with a salt of a tertiary amine in the presence of a quaternary ammonium compound as catalyst.
Inventors
- 👤 Horst Rutzen
- 👤 Peter Nikolaus
- 👤 Martin Bischoff
- 👤 Rudolf Lehmann
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 23:43
CPC Classifications
A; A01; A01N; A01N33/00; A01N33/02; A01N33/12; C; C11; C11D; C11D1/00; C11D1/38; C11D1/62; D; D06; D06M; D06M13/00; D06M13/322; D06M13/385; D06M13/46; D06M13/463; D06M2200/00; D06M2200/50
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
240 words
A process for the preparation of a quaternary ammonium compound comprising the steps of (I) forming an aqueous mixture of (a) a compound containing a terminal epoxy group selected from the group consisting of (i) a compound of the formula ##STR5## wherein R 1 is a straight or branched chain aliphatic hydrocarbon group having 4 to 16 carbon atoms or a group of the formula ##STR6## wherein n is an integer of from 4 to 16, and (ii) a compound of the formula ##STR7## wherein m is an integer of from 1 to 10, and R 2 is hydrogen, or a straight or branched chain aliphatic hydrocarbon group having from 1 to 24 carbon atoms, or a group of the formula ##STR8## (b) a salt of a tertiary amine which contains one or more alkyl, hydroxyalkyl, or aralkyl groups wherein such groups each contain less than 10 carbon atoms, and wherein the tertiary amines can optionally contain a C 10 to C 20 straight or branched chain alkyl or alkenyl group; and (c) from about 0.5 to about 10% by weight, based on the theoretical weight of the quaternary ammonium compound reaction product, of a quaternary ammonium catalyst; and (II) heating said aqueous mixture to a temperature in the range of from about 40° to about 100° C. for a period of time sufficient to produce a quaternary ammonium compound from the reaction between compound (a) and compound (b) above.
Claim 2
Dependent Claim
240 words
A process for the preparation of a quaternary ammonium compound comprising the steps of (I) forming an aqueous mixture of (a) a compound containing a terminal epoxy group selected from the group consisting of (i) a compound of the formula ##STR5## wherein R 1 is a straight or branched chain aliphatic hydrocarbon group having 4 to 16 carbon atoms or a group of the formula ##STR6## wherein n is an integer of from 4 to 16, and (ii) a compound of the formula ##STR7## wherein m is an integer of from 1 to 10, and R 2 is hydrogen, or a straight or branched chain aliphatic hydrocarbon group having from 1 to 24 carbon atoms, or a group of the formula ##STR8## (b) a salt of a tertiary amine which contains one or more alkyl, hydroxyalkyl, or aralkyl groups wherein such groups each contain less than 10 carbon atoms, and wherein the tertiary amines can optionally contain a C 10 to C 20 straight or branched chain alkyl or alkenyl group; and (c) from about 0.5 to about 10% by weight, based on the theoretical weight of the quaternary ammonium compound reaction product, of a quaternary ammonium catalyst; and (II) heating said aqueous mixture to a temperature in the range of from about 40° to about 100° C. for a period of time sufficient to produce a quaternary ammonium compound from the reaction between compound (a) and compound (b) above.
Claim 3
Dependent Claim
64 words
A process in accordance with claim 1 wherein the salt of a tertiary amine I(b) is first formed by dissolving the tertiary amine precursor in water, adding an acid thereto to form an aqueous solution of a salt of the tertiary amine, and the compound containing a terminal epoxy group (I)(a) and the quaternary ammonium catalyst (I)(c) are added to the aqueous salt solution.
Claim 4
Dependent Claim
19 words
A process in accordance with claim 1 or 2 wherein the reaction is carried out at normal atmospheric pressure.
Claim 5
Dependent Claim
23 words
A process in accordance with claim 3 wherein the reaction temperature is in the range of from about 80° to about 95° C.
Claim 6
Dependent Claim
25 words
A process in accordance with claim 1 wherein the epoxy compound (I)(a) and the tertiary amine salt (I)(b) are present in approximately chemically equivalent quantities.
Claim 7
Dependent Claim
23 words
A process in accordance with claim 5 wherein the equivalent ratio of epoxy compound (I)(a) to tertiary amine salt (I)(b) is about 1:1.1.
Claim 8
Dependent Claim
23 words
A process in accordance with claim 1 wherein the quaternary ammonium catalyst is identical to the quaternary ammonium compound produced by said reaction.
Claim 9
Dependent Claim
20 words
A process in accordance with claim 1 wherein the catalyst is dimethyldi(C 12 -C 16 alkyl or alkenyl) ammonium chloride.
Claim 10
Dependent Claim
19 words
A process in accordance with claim 1 wherein the epoxy compound (I)(a) contains from 10 to 20 carbon atoms.
Claim 11
Dependent Claim
28 words
A process in accordance with claims 1 or 9 wherein the tertiary amine salt (I)(b) contains an alkyl or alkenyl group having from 10 to 20 carbon atoms.
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) | 1988-01-08 | 1988-07-09 | 1989-01-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-01-08 | 1992-07-09 | 1993-01-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-01-08 | 1996-07-09 | 1997-01-08 | $7700.00 | Window Closed / Lapsed |