Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1993-08-06
1994-08-30
Brust, Joseph Paul
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C07D23304
Patent
active
053429613
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
This invention relates to a process for the production of low-viscosity imidazolinium surfactants by reaction of 1-hydroxyethyl-2-alkyl imidazolines with neutralized quaternizing agents and hydrolysis of the quaternization products obtained with aqueous bases.
STATEMENT OF RELATED ART
Imidazolinium surfactants belong to the class of so-called amphoteric surfactants which may be obtained from 1-hydroxyethyl-2-alkyl imidazolines, for example by quaternization with chloroacetates or chloropropionates, cf. J. Falbe (Ed.), Surfactants in Consumer Products, Springer-Verlag Berlin (1987), pages 116-117. Numerous processes for the production of these imidazolinium surfactants have been described, cf. U.S. Pat. Nos. 2,528,378, 2,773,068, DE-A 20 63 424 (GB-B 1,352,770), GB-B 930,296, EP-B 0 001 006, U.S. Pat. No. 4,269,730 and EP-B 0 040 346. The objective of these processes is inter alia the production of imidazolinium surfactants which are substantially free from diamines and chloroacetic acid or chloropropionic acid.
DE-A 36 41 871 describes a process of the type mentioned at the beginning, in which 1-hydroxyethyl-2-alkyl imidazolines are added at an increasing rate to a solution of the quaternizing agents over a period of at least one hour at temperatures of 55.degree. to 65.degree. C., the reaction mixture obtained is kept at 55.degree. to 65.degree. C. for another 80 to 100 minutes, the temperature is then increased to a value of 75.degree. to 85.degree. C. for another 80 to 100 minutes, 0.85 to 1.0 mol of an alkali metal hydroxide, based on the quantity of quaternizing agent introduced, is then added to the reaction mixture over a period of 15 minutes at a temperature of at least 80.degree. C., a pH value of 11.5 to 12.0 being established, and the reaction mixture is kept at a temperature of 80.degree. to 90.degree. C. for 140 to 180 minutes after the addition. However, it has been found that, where this process is carried out on an industrial scale, the necessary metering and temperature parameters have to be strictly adhered to if the imidazolinium surfactants are to have the low viscosity required.
DESCRIPTION OF THE INVENTION
Accordingly, the process according to the invention is directed at improving the process according to DE-A 36 41 871 so that, in particular, the imidazoline no longer has to be added to the quaternizing agent with the hitherto necessary precision. In the process according to the invention, the imidazoline may now be added at any rate, the pH value remaining in a constant range so that there is no unwanted premature opening of the imidazoline ring.
According to the invention, this problem has been solved by a process having features a to d, temperature into an aqueous solution of the neutralized quaternizing agents in molar ratios of imidazoline derivatives to quaternizing agents of 1:1.5 to 1:3, 85.degree. C. for 30 to 120 minutes, used in step a, is added over a period of 30 to 120 minutes at a temperature of 75.degree. to 85.degree. C. and 90.degree. C. for 140 to 220 minutes; to 0.5 mol, based on 1-hydroxyethyl-2-alkyl imidazolines to be added, of carboxylic acids is used in step a and acids are added to the reaction mixture obtained in step d so that a pH value of 7 to 10 is established when the reaction mixture is diluted with water to a product concentration of 10% by weight.
1-Hydroxyethyl-2-alkyl imidazolines suitable for use in the process according to the invention are, in particular, technical mixtures of these compounds according to DE-A 36 41 871 which contain at least 80% by weight of the 1-hydroxyethyl-2-alkyl imidazolines and at most 3% by weight diamides. 1-Hydroxyethyl-2-alkyl imidazolines obtainable by reaction of aminoethyl ethanolamine with linear or branched, saturated or unsaturated C.sub.6-22 fatty acids, including technical mixtures thereof, are particularly suitable. Typical examples of such fatty acids are lauric acid, caproic acid, caprylic acid, capric acid, myristic acid, palmitic acid, stearic acid, oleic acid, arachi
REFERENCES:
patent: 2528378 (1950-10-01), Mannheimer
patent: 2773066 (1956-12-01), Mannheimer
patent: 4269730 (1981-05-01), Wechsler et al.
patent: 4833253 (1989-05-01), Ploog et al.
Jaensch Sven
Ploog Uwe
Steinberner Udo
Uphues Guenter
Brust Joseph Paul
Drach John E.
Gabilan Mary Susan H.
Henkel Kommanditgesellschaft auf Aktien
Jaeschke Wayne C.
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