Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1996-10-18
1998-06-30
Kight, John
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 41, 5361231, 536124, 25217417, C07H 1502, C07H 100
Patent
active
057735956
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
This invention relates to cationic sugar surfactants obtainable by reaction of alkyl and/or alkenyl oligoglucosides with quaternized halogen compounds or quaternized epoxide compounds or by reaction of the glucosides with halogen compounds and amines, to processes for the production of the cationic surfactants, to surface-active formulations containing the cationic sugar surfactants mentioned and to their use for the production of surface-active formulations.
STATEMENT OF RELATED ART
Depending on their substitution pattern, cationic surfactants of the tetraalkyl ammonium salt type are important constituents of such different products as fabric softeners, hair-care formulations, antistatic agents and sanitary cleaners.
Unfortunately, a major disadvantage of these products is that they cannot readily be processed to form stable, high-solids dispersions of low (1984)!. Accordingly, the use of typical tetraalkyl ammonium salts, such as dimethyl distearyl ammonium chloride for example, involves high costs for the packaging, storage and transport of the dilute aqueous formulations. Accordingly, there is an urgent need to remedy this situation.
Another disadvantage of cationic surfactants is that their biological degradability is questionable. It is normally assumed by experts that cationic surfactants are only degraded to a minor extent by microorganisms in a sewage treatment plant and are largely precipitated through salt too, there is a need to develop cationic surfactants with improved ecological compatibility.
There has been no shortage of attempts in the past to provide new cationic surfactants which would represent improvements over the prior art in one respect or the other. For example, there are the so-called "esterquats"--cationic surfactants based on aminoalcohols and fatty acids in Tens. Surf. Deterg., 30, 186 (1993) and M. Brock in Tens. Surf, Deterg. 30, 394 (1993).
Cationic sugar surfactants are also known from the prior art. Thus, according to U.S. Pat. No. 3,931,148 (BASF), glucose or starch is reacted with 0.5 to 1.2 moles of 3-chloropropane-1,2-diol in the presence of sulfuric acid, the hydrochloric acid released is neutralized and the glucoside is subsequently condensed with an amine. However, the performance properties of these products were unsatisfactory.
U.S. Pat. No. 4,719,272 (National Starch) describes cationic surfactants which are produced by reaction of glycidyl, halohydrin or haloalkyl glycosides with unsaturated amines or amidoamines, such as N,N-dimethylaminopropyl methacrylamide for example.
The subject of WO 90/15809 (Henkel Corp.) is the acetalization of cationic starch. EP-A1 0 432 646 (Union Carbide) and a corresponding article by S. Polovsky in Cosm. Toil. 106, 59 (1991) describe alkyleneoxide-containing QUATS based on alkyl polyglucosides and their use in cleaning products.
Finally, a synoptic article by T. Bocker and J. Thiem entitled "Synthese und Eigenschaften von Kohlen-hydrattensiden (Synthesis and Properties of Carbohydrate Surfactants)" in Tens. Surf. Dot. 26, 324 (1989) reports on the multistage reaction of dodecyl-.beta.-D-glucopyranoside with secondary amines.
These known products are also attended by the disadvantage that they do not meet performance requirements and/or can only be obtained with considerable effort.
Accordingly, the problem addressed by the present invention was to provide new biologically degradable quaternary ammonium compounds based on alkyl glycosides which would be distinguished by advantageous performance properties, could be used in a number of different formulations and could be produced in high yields with comparatively little effort.
DESCRIPTION OF THE INVENTION
The present invention relates to cationic sugar surfactants corresponding to formula (I): ##STR2## in which R.sup.1 represents an alkyl and/or alkenyl radical containing 4 to 22 carbon atoms, Y is hydrogen or has the same meaning as Z and Z is a group corresponding to formula (II): ##STR3## in which R.sup.2 and R.sup.3 independently of one anot
REFERENCES:
patent: 3931148 (1976-01-01), Langdon
patent: 4719272 (1988-01-01), Tsai et al.
patent: 5227481 (1993-07-01), Tsai et al.
patent: 5374716 (1994-12-01), Biermann et al.
Chemical Abstracts, vol. 118, No. 9, issued 01 Mar. 1993, Yamamuro et al, "Preparation of nitrogen-containing glycosides as surfactants", p. 880, col. 1, abstract No. 81322m, Jpn. Kokai Tokkyo Koho JP 04,225,995.
C.R. CESIO World Surfactant Congress, Paris, vol. II (1984), p. 76.
Tens. Deterg. 25, 1988, p. 134.
C.R. CED Congress, Barcelona, 1992, p. 167.
Tens. Surf. Deterg. 30, 1993, pp. 186, 394.
Cosm. Toil. 106, 1991, p. 59.
Tens. Surf. Det. 26, 1989, pp. 318-324.
Surfactants in Consumer Products, Springer, Verlag, Berlin, 1987, pp. 54-124.
Kayalysatoren, Tenside und Mineraloladditive, Thieme Verlag, Stuttgart, 1978, pp. 123-217.
"Kosmetische Farbemittel" of the Farbstoffkommission der Deutschen Forschungsgemeinschaft, Verlag Chemie, Weinheim, 1984, pp. 81-106.
Hensen Hermann
Kahre Joerg
Tesmann Holger
Weuthen Manfred
Drach John E.
Henkel Kommanditgesellschaft auf Aktien
Jaeschke Wayne C.
Kight John
Trzaska Steven J.
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