Alk(en)yldicarboxylic acid bisesters, their use, and processes f

Details Alk(en)yldicarboxylic acid bisesters, their use, and processes f Alk(en)yldicarboxylic acid bisesters, their use, and processes f

1997-08-15

1999-02-16

Barts, Samuel

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ester doai

504313, 426654, 510505, 510513, 514937, 554223, 554224, 554148, A61K 31235

Patent

active

058721495

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP96/00657 filed Feb. 15, 1996.


I. SUBJECT OF THE INVENTION

The present invention relates to monomeric, oligomeric and polymeric bisesters of alkyl- or alkenyldicarboxylic acid derivatives and polyalcohols, and their use as solubilizers, emulsifiers and/or detergents. In particular, the bisesters are advantageously used in cosmetic compositions, detergents and cleaners, pharmaceutical compositions, foodstuffs and crop protection compositions. The invention furthermore relates to a process for preparing these bisesters.


I. BACKGROUND OF THE INVENTION

In the surfactant and emulsifiers sector, in recent years nonionic surface-active substances which are readily biodegradable, have a low toxicity and thus possess good environmental compatibility have increasingly come to the fore.
An important group of nonionic compounds of this type are esters of fatty acids and polyalcohols, such as sucrose esters, sorbitan esters and glycerol and polyglycerol fatty acid esters. In these compounds a polyalcohol group is esterified with a hydrophobic fatty acid radical.
Most products of the classes of compound mentioned are too nonpolar to be employed in aqueous formulations as a surfactant. The more hydrophilic products of this compound type prove in some properties such as foaming and wetting power and the interfacial and surface tension to be still in need of improvement.
JP 051 25 014 discloses monoesters of alkenylcarboxylic anhydrides with hydrophilic compounds, such as polyglycerol, and their use as surfactants.
WO 94/00508 discloses surfactants in which a polyethylene glycol chain is bonded to an alk(en)ylsuccinic acid radical. The polyethylene glycol bisesters described have at least 13 carbon atoms.
DE 42 38 032 discloses bisesters of alk(en)ylsuccinic acid derivatives with polyethylene glycols and their use as skin conditioners.
EP 01 07 199 and BE 898 441 disclose polyoxyalkylenemonoesters of alk(en)ylsuccinic acid derivatives and various intended uses of these compounds.
A disadvantage in these products is in particular the lack of hard water stability and the excessively high interfacial tensions and thus the excessively low solubilizing and emulsifying action.
The use of bisesters of alkyl- or alkenylmalonic acid derivatives, -succinic acid derivatives and -glutaric acid derivatives and polyalcohols which, on the one hand, have a hydrophobic radical and on the other hand at least two polyalcohol components, as solubilizers, emulsifiers or detergents, in particular in detergents, cleaners or personal hygiene compositions, pharmaceutical compositions, foodstuffs or crop protection compositions, has not been described until now.
J 6 00 18 584 discloses alkenylsuccinic acid bisglycerol esters for use as corrosion inhibitors in oil-soluble medium.
In SU 457 754 and in DL 163 348, alkenylsuccinic acid polyglycerol bisesters are employed in electrolytes for silver-plating or for tin baths.
J 5 70 65 793, SU 432 172, U.S. Pat. No. 4,234,435 and U.S. Pat. No. 4,159,958 disclose applications of alkenylsuccinic acid polyglycerol monoesters or bisesters in lubricating oils and cooling lubricants.
DDR 40 624 discloses a process for preparing dicarboxylic acid polyglycerol bisesters and mentions the wetting agent properties of these compounds.
The present invention is based on the object of providing compounds which can be used as detergents, solubilizers and emulsifiers and which do not have the disadvantages described above. The compounds according to the invention should be able to display their advantageous actions, in particular in aqueous or in aqueous/ethanolic systems in which poorly soluble or insoluble substances are to be solubilized or emulsified or from which substances are to be removed with the aid of the detergent activity of the compounds according to the invention.
In particular, the compounds according to the invention should be utilizable in detergents and cleaners and also in cosmetic compositions. The compounds should furthermore be physiologically or phytophysiolo

REFERENCES:
patent: 2650211 (1953-08-01), Dannenberg et al.
patent: 4159958 (1979-07-01), de Vries
patent: 4234435 (1980-11-01), Meinhardt et al.

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