Thiodiglycol alkoxylate derivatives, a process for their product

Details Thiodiglycol alkoxylate derivatives, a process for their product Thiodiglycol alkoxylate derivatives, a process for their product

1993-03-05

1994-05-03

Lieberman, Paul

Compositions

Fire-extinguishing

Foam-stabilizant or colloid-stabilizant containing

252 86, 252 89, 568 27, 568 28, 554227, 560263, 560264, D06M 1008

Patent

active

053085124

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND OF THE INVENTION

1. Field of the Invention
This invention relates to new thiodiglycol alkoxylate derivatives, to their production by reaction of thiodiglycol with alkylene oxides, subsequent reaction with .alpha.-olefin epoxides or monocarboxylic acids and oxidation with hydrogen peroxide to form the corresponding mono- and/or bis-ethers or mono- and/or bis-esters of thiodiglycol alkoxylate sulfoxides or sulfones and to the use of the thiodiglycol alkoxylate sulfoxides or sulfones as fabric softeners.
Hitherto, considerable practical significance has been attributed to quaternary ammonium compounds, particularly dimethyl distearyl ammonium chloride, in the field of domestic and institutional fabric softeners (see P. Vogel and H. Kru.sym.mann, Seifen, ole, Fette, Wachse, Vol. 111, pages 567 to 574, 1985 and L. Godefroy and H. Hein, Seifen, ole, Fette, wachse, Vol. 115, pages 3 to 8, 1989).
In view of the increasing consideration being given to the storability and viscosity characteristic and also to the biodegradability of highly concentrated fabric softeners, numerous proposals for replacing these components by nitrogen-free substitute compounds or corresponding systems have been published. These proposals encompass both inorganic components, more particularly inorganically insoluble components, such as layer silicate compounds (see for example DE-PS 23 34 899), and also selected organic components, for example disalts of long-chain .alpha.-sulfofatty acids and combinations of such systems (see DE-PS 36 04 039).
2. Discussion of Related Art
Thiodiglycol derivatives, a process for their production and their use as fabric softeners are already known from the teaching of applicants' German patent application P 39 36 862.9. However, in view of their limited solubility in water and their high melting points, the compounds in question can only be formulated as expensive mixtures in stable dispersions.
Accordingly, the problem addressed by the present invention was to provide a hitherto unreported class of nitrogen-free inorganic compounds for use as rinse cycle fabric softeners which, on the one hand, would be easier to formulate through greater dispersion stability and, on the other hand, would be distinguished by better feel behavior compared with the compounds described above.


DESCRIPTION OF THE INVENTION

Other than in the operating examples, or where otherwise indicated, all numbers expressing quantities of ingredients or reaction conditions used herein are to be understood as modified in all instances by the term "about".
In a first embodiment, therefore, the present invention relates to new alkoxylated thiodiglycol sulfoxide derivatives or thiodiglycol sulfone derivatives corresponding to general formula I ##STR2## in which X.sub.1 and X.sub.2 may be the same or different and have the following meanings: atoms;
The thiodiglycol alkoxylate compounds of general formula (I) according to the invention are a hitherto unreported class of compounds. They are prepared by reaction of alkoxylated thiodiglycol compounds with .alpha.-olefin epoxide compounds containing 8 to 30 carbon atoms in the molecule or by the corresponding reaction of alkoxylated thiodiglycol compounds with alkyl monocarboxylic acids of comparable chain length and subsequent oxidation with hydrogen peroxide to the corresponding sulfoxides or sulfones.
According to the invention, the alkoxylated thiodiglycol compounds are obtained by the base-catalyzed reaction of thiodiglycol with alkylene oxides. The alkoxylation is generally carried out by the method known from the literature for alcohols at a reaction temperature in the range from about 100 to 200.degree. C., under a pressure of 1 to 50 bar and in a nitrogen atmosphere.
In one preferred embodiment of the invention, a catalytic quantity of methanolic potassium hydroxide solution is added to the thiodiglycol in an autoclave and the thiodiglycol is reacted with ethylene oxide at 140 to 150.degree. C. to form the ethoxylated thiodiglycols, the pressure not exceeding 5.times.10.sup.

REFERENCES:
patent: 4830636 (1989-05-01), Horodysky
Trofimov, Zh. Prikl. Khim., vol. 48, pp. 626-628 1975.
Vogel & Krussman & Seifen, Ole, Fette, Wachse, vol. 115, 1989, pp. 3-8 Article Unavailable.
J. Falbe, Surfactants in Consumer Products, Springer, 1987, pp. 87-90.
Vogel & Krussmann, Seifen, Ole, Fette, Wachse, vol. III, 1985, pp. 567-574 1985.

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