Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1993-09-16
1996-04-16
Robinson, Douglas W.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536115, 536116, 536119, 536120, 5361231, 53612313, 568864, 568865, 560182, C07H 504, C07H 506, C07H 1302, A01N 4304
Patent
active
055083943
DESCRIPTION:
BRIEF SUMMARY
It is an object of the present invention to provide novel substances. It is a further object of the present invention to provide detergent additives which are improved compared with the prior art.
We have found that the first object is achieved by esters of citric acid or acetylcitric anhydride and polyhydroxy compounds, which are obtainable by esterifying of sugarcarboxylic acids, C.sub.2 -C.sub.5 -alkylglucosides, hydroxy-alkylglucosides, sugar alcohols and oxidation products of oligosaccharides which contain up to 4 monosaccharide units, amino-sorbitol, sorbitol, aminodisorbitol, glucosamine, N-acetylglucosamine and trishydroxyethylmelamine, 1 molecule of a compound (a). We have found that the second object is achieved by using citric esters as additives in low-phosphate or phosphate-free detergent formulations in an amount of from 0.1 to 30% by weight, based on the formulation.
The citric esters are prepared by reacting the components described above under (a) and (b). This reaction is customarily carried out using the known acidic catalysts for esterifications, eg. sulfuric acid, paratoluenesulfonic acid, benzenesulfonic acid or hydrochloric acid. However, in principle, it can also be carried out without a catalyst. The citric acid can also be partially neutralized prior to the esterification, preferably in the course of reaction with natural substances or derivatives thereof; for example, 1 mol of citric acid is neutralized with from 0.1 to 2.9, preferably from 0.5 to 2.0, mol of a monoacid base, e.g. NaOH. The esterification can be carried out in substance, i.e. by heating the components (a) and (b) and distilling off water, or else in the presence of an inert diluent. The inert diluent, e.g. toluene, xylene or isopropylbenzene, here acts by means of the amount of water which has distilled off, the acid number and the saponification number of samples of the reaction mixture. The esterification in substance is preferably carried out in a kneading reactor. In general, the esterification is carried out in a kneader when relatively viscous esterification products are formed. Depending on the ratio of the components (a) and (b) and depending on the degree of conversion of the esterification, it is also possible to prepare linear or branched oligomeric esters from a plurality of building blocks conforming to (a) and (b).
As sugarcarboxylic acids, it is possible to use the oxidation products of sugars of from 4 to 7 carbon atoms, e.g. gluconic acid, glucoheptonic acid, glucaric acid, galactaric acid, glucuronic acid or mannonic acid and also the corresponding lactones, e.g. gluconolactone and glucoheptonolactone.
Suitable compounds (b) also include alkylglucosides and alkylpolyglucosides, alkylmaltosides and alkylmaltotriosides. The alkyl group can be a C.sub.2 -C.sub.5, preferably a C.sub.2 -C.sub.4 -alkyl group, e.g. ethyl, n-propyl, isopropyl, n-butyl or isobutyl. The alkyl group can also be substituted, for example by hydroxyl. Suitable compounds of this type are for example hydroxyethyl glucoside and hydroxypropyl glucoside and also the corresponding polyglucosides. The polyglucosides contain an average of from 1.1 to 10, preferably from 1.3 to 3, glucoside units.
Oligosaccharides which contain up to 4 monosaccharide units are for example maltose, maltotriose, maltotetraose, saccharose, lactose, leucrose, isomaltulose, chitobiose, chitotriose, chitotetraose and the derivatives obtainable therefrom by loss of the acetyl groups. The monosaccharide units of the oligosaccharides can come from any customary monosaccharide, in particular from glucose, galactose, fructose or mannose. Sugar alcohols of oligosaccharides which contain up to 4 monosaccharide units are obtainable from the above-mentioned oligosaccharides by reduction. The oxidation products of the oligosaccharides mentioned include for example saccharosetricarboxylic acid and lactobionic acid.
Further suitable compounds of group (b) are aminosorbitol, aminodisorbitol, glucosamine, N-acetylglucosamine, triethanolamine and trishydroxyethylmelamine.
REFERENCES:
patent: 2813892 (1957-11-01), Mehltretter
patent: 3563903 (1971-02-01), Schmadel et al.
patent: 3661955 (1972-05-01), Centolella et al.
patent: 3859224 (1975-01-01), Kandler et al.
patent: 3872020 (1975-03-01), Yamagishi et al.
patent: 4797481 (1989-01-01), Garlisi et al.
Derwent Abstracts, AN 77-38805Y, JP 52049203, Apr. 20, 1977.
Baur Richard
Boeckh Dieter
Hartmann Heinrich
Kappes Elisabeth
Kud Alexander
BASF - Aktiengesellschaft
Robinson Douglas W.
White Everett
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