Quaternized esters

Details Quaternized esters Quaternized esters

1992-11-16

1994-03-22

Prescott, Arthur C.

Organic compounds -- part of the class 532-570 series

Organic compounds

Fatty compounds having an acid moiety which contains the...

554108, 554110, C07C21900, D06M 1346, C11D 162

Patent

active

052966224

DESCRIPTION:

BRIEF SUMMARY
This invention relates to quaternized esters obtainable by reaction of unsaturated fatty acids--containing at least 40 mol-% trans-configured double bonds--or esters thereof with alkanolamines and subsequent quaternization of the reaction products with alkylating agents and to the use of the products as fabric softeners.
Quaternized esters of saturated fatty acids and alkanolamines are used as fabric softeners (DE-A-16 19 058, DE-A-17 94 68). Particular significance is attributed in this regard to products obtainable by reaction of 2 mol saturated fatty acid with 1 mol triethanolamine and subsequent quaternization with dimethyl sulfate or methyl chloride. Although fabrics treated with quaternized esters of this type show good softness, they often exhibit unwanted hydrophobicity which is reflected in poor wettability or water absorption of the treated fabrics.
There has been no shortage of attempts in the past to solve this problem.
For example, it is known from U.S. Pat. No. 3,915,867 that quarternized esters of mixtures of saturated and unsaturated fatty acids, for example of the type readily obtainable by hydrolysis of natural fats and oils, show good softening power with triethanolamine. It is also disclosed in the patent specification that quaternized esters based on unsaturated fatty acids and alkanolamines have no fabric-softening properties. Accordingly, mixtures of quaternized esters based on saturated and unsaturated fatty acids show poorer performance properties than quaternized esters which have been produced using only saturated fatty acids.
Quaternized triethanolamine triesters based on saturated or monounsaturated fatty acids containing 12 to 22 carbon atoms are known from EP-A-0 239 910. However, products of this type, which have three long fatty acid residues and one short-chain alkyl group, show unsatisfactory softening properties.
Finally, according to the teaching of EP-A 0 284 036, technical mixtures of esters of saturated and unsaturated fatty acids with glycerol, for example of the type obtainable from natural fats and oils, can be transesterified with alkanolamines and then quaternized. Since quaternized esters of this type in turn contain unsaturated components, they are inferior to saturated products in terms of softness.
Accordingly, the problem addressed by the present invention was to provide quaternized esters of fatty acids with alkanolamines which would be capable both of providing fabrics with good softness and of imparting a high degree of hydrophilicity.
The present invention relates to quaternized esters obtainable by
A) reaction of monounsaturated C.sub.16-22 fatty acids containing at least 40 mol-% trans-configured double bonds or esters thereof with glycerol or aliphatic C.sub.1-4 alcohols with alkanolamines corresponding to formula (I) ##STR1## in which R.sup.1 and R.sup.2 are independently of one another C.sub.2-4 hydroxyalkyl groups and R.sup.3 is either a C.sub.2-4 hydroxyalkyl group or a C.sub.1-22 straight or branched alkyl group, and
B) subsequent quaternization of the reaction products with alkylating agents.
The invention is based on the observation that quaternized esters of fatty acids containing at least 40 mol-% trans-configured double bonds with alkanolamines provide textiles with surprisingly good softness during the softening treatment and, in addition, have a less hydrophobicizing effect.
Suitable fatty acids for the preparation of the quaternized esters according to the invention are, in particular, elaidic acid and technical fatty acid fractions rich in elaidic acid which contain at least 40 mol-% fatty acids having trans-configured double bonds.
Other suitable starting materials for the production of the quaternized esters are esters of the above-mentioned fatty acids with alcohols containing 1 to 4 carbon atoms. Typical examples are ethyl, n-propyl, i-propyl, n-butyl or, more particularly, methyl esters. In addition, in one particular embodiment of the invention, the fatty acids may be present as full or partial esters of glycerol.
Unsaturated fatt

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patent: 5068120 (1991-11-01), Yarger et al.
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Fette, Seifen und Anstrichmittel, vol. 88, Oct. 1986, M. Munzing et al.: "Kinetik der Fetthartung und Vergleich verschiedener Katalysatoren", pp. 387-391.
J. Am. Chem. Soc., 79, 4765 (1967), R. L. N. Harris et al.: "Mass Spectrometry in Structural and Sterochemical Problems. CXXXII. Electron Impact Induced Alkyl and Aryl Rearrangements in .alpha.,.beta.-Unsaturated Cyclic Ketones".
DIN 53 924, Nov., 1978.

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