Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Patent
1995-09-18
1997-09-23
Carr, Deborah D.
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
554108, 554109, 554110, 25217422, 252541, C07C10100
Patent
active
056706774
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP94/00716 filed Mar. 9, 1994.
FIELD OF THE INVENTION
This invention relates to a process for the production of color- and odor-stable quaternized fatty acid triethanolamine ester salts, in which fatty acids are reacted with triethanolamine, the esterification products are treated with peroxide compounds and alkali metal boranates and the quaternization is carried out in the presence of selected stabilizers.
PRIOR ART
Quaternized fatty acid triethanolamine ester salts, so-called (ester quats), are cationic surfactants which are acquiring increasing significance by virtue of their excellent fabric-softening effect and their high ecotoxicological compatibility. The articles by O. Ponsati in C.R. CED Congress, Barcelona, 1992, page 167 and R. Puchta in C.R. CED Congress, Sitges, 1993, page 59, are cited as representative of the literature available on this subject.
The ester quats are normally produced in a two-stage process in which triethanolamine is first partly esterified with fatty acids and the reaction product is subsequently alkylated or quaternized with ethylene oxide. Hypophosphorous acid and sodium hypophosphite have proved to be optimal catalysts for the esterification step. However, during working up, particularly at relatively high temperatures, decomposition of the hypophosphorous acid or its salts can occur and small quantities of phosphines are formed, resulting in an adverse effect on the odor of the product. Another problem in the production of ester quats is that products light in color after production are not stable in storage and can darken to a considerable extent with time which limits their commercial usefulness.
Accordingly, the problem addressed by the present invention was to develop a process for the production of quaternized fatty acid triethanolamine ester salts which would be free from the disadvantages described above.
DESCRIPTION OF THE INVENTION
The present invention relates to a process for the production of color- and odor-stable quaternized fatty acid triethanolamine ester salts corresponding to formula (I): ##STR1## in which R.sup.1 CO is an acyl radical containing 6 to 22 carbon atoms, the same meaning as R.sup.1 CO, CH.sub.2 O).sub.q H group, q is a number from 1 to 12, hypophosphorous acid, esterification products and and hydroxycarboxylic acids as stabilizers.
It has surprisingly been found that only the combination of features a), b) and c) leads to light-colored ester quats which are satisfactory in regard to odor and are stable in color, even in the event of prolonged storage. The invention includes the observation that, among the large number of known antioxidants, only selected substances are capable of stabilizing ester quats against color deterioration. Another significant observation is that even the proposed stabilizer system can only perform its function satisfactorily when it is added to the intermediate products, i.e. to the as yet unquaternized esters, and not to the end products.
Quaternized fatty acid triethanolamine ester salts are known substances which may obtained by the relevant methods of preparative organic chemistry. In this connection, reference is made to International patent application WO 91/01 295 (Henkel), according to which triethanolamine is partly esterified with fatty acids in the presence of hypophosphorous acid and, after has been passed through, the esterification product is subsequently quaternized with dimethyl sulfate or ethylene oxide.
The process according to the invention is preferably applied to ester quats which are produced using fatty acids corresponding to formula (II): caprylic acid. capric acid, lauric acid, myristic acid, palmitic acid, isostearic acid, stearic acid, oleic acid, elaidic acid, arachic acid, behenic acid and erucic acid and technical mixtures thereof such as are formed, for example, in the pressure hydrolysis of natural fats and oils. Technical C.sub.12/18 coconut oil fatty acids and, in particular, partly hydrogenated C.sub.16/18 tallow or palm oil fatty acids
Bigorra Llosas Joaquim
Obiols Oriol Ponsati
Carr Deborah D.
Henkel Kommanditgesellschaft auf Aktien
Jaeschke Wayne C.
Millson Jr. Henry E.
Szoke Ernest G.
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