Organic compounds -- part of the class 532-570 series – Organic compounds – Nitriles
Patent
1997-05-12
1998-10-13
Richter, Johann
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitriles
558400, 558402, 524397, 524396, 524186, 514535, 514536, 512 22, 424 59, 424 60, 424400, 424401, 252401, 252403, 252405, C07C25507, A61K 742
Patent
active
058213805
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP95/04312 filed Nov. 3, 1995.
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to novel 2-cyanoacrylic esters of the formula I ##STR3## where R.sup.1 and R.sup.2 are each hydrogen or a radical having an iso- or heterocyclic ring system with at least one iso- or heteroaromatic nucleus, and at least one of the radicals R.sup.1 or R.sup.2 must be different from hydrogen, ##STR4## where m is from 2 to 8, and X is, when n>2, the radical of an n-hydric aliphatic or cycloaliphatic polyol having 3-20 carbon atoms, it also being possible for a cycloaliphatic radical to contain 1 or 2 hetero atoms, and for an aliphatic radical to be interrupted by up to 8 non-adjacent oxygen atoms, sulfur atoms, imino or C.sub.1 -C.sub.4 -alkylimino groups.
The invention furthermore relates to a process for preparing the compounds I, to the use thereof as stabilizers, in particular against the action of light, for organic materials, in particular for cosmetic or dermatological preparations, plastics or paints, and to organic materials which contain the compounds I.
2. Description of the Background
U.S. Pat. No. 3,215,725 and DE-A 41 22 475 disclose 2-cyanoacrylic esters of monohydric and dihydric alcohols as light stabilizers for plastics and paints.
However, these compounds have the technical disadvantage of a relatively high volatility. Since, moreover, they are only conditionally compatible with many organic materials, especially with polyolefins, they are prone, especially on storage at elevated temperature, to migrate and consequently display exudation.
SUMMARY OF THE INVENTION
It is an object of the present invention to remedy these disadvantages by novel stabilizers of the 2-cyanoacrylic ester type.
We have found that this object is achieved by the 2-cyanoacrylic esters of the general formula I defined at the outset.
We have furthermore found a process for preparing these compounds, their use as light protection factors or stabilizers for organic materials, and organic formulations which contain these compounds as stabilizers.
DETAILED DESCRIPTION OF THE INVENTION
If the radicals R.sup.1 and R.sup.2 are different, the 2-cyanoacrylic ester groups of I may be either in the cis or the trans form. The preparation of the compounds usually results in mixtures of these isomers. It is possible to separate these isomers, but this is unnecessary for most industrial applications.
Suitable organic radicals for R.sup.1 and R.sup.2 are, in general, cyclic structures which contain at least one iso- or heteroaromatic nucleus, which is preferably linked directly to the 3-C atom of the acrylic group but can also be linked to this carbon atom via aliphatic or cycloaliphatic groups and via a linker --NR.sup.3 --.
R.sup.1 or R.sup.2 is preferably a radical of the formula III ##STR5## where R.sup.3 is hydrogen or C.sub.1 -C.sub.10 -alkyl, r is 0 or 1, and R.sup.4 to R.sup.8 are each, independently of one another, hydrogen, C.sub.1 -C.sub.8 -alkyl, chlorine, bromine, cyano, nitro, amino, mono(C.sub.1 -C.sub.4 -alkyl)amino, di(C.sub.1 -C.sub.4 -alkyl)amino, hydroxyl, C.sub.1 -C.sub.8 -acyl, C.sub.1 -C.sub.8 -acyloxy, C.sub.1 -C.sub.18 -alkoxy, C.sub.1 -C.sub.12 -alkoxycarbonyl, C.sub.3 -C.sub.6 -cycloalkyl or C.sub.3 -C.sub.6 -cycloalkoxycarbonyl.
Suitable radicals R.sup.3 besides hydrogen are C.sub.1 -C.sub.10 -alkyl isopentyl, sec-pentyl, tert-pentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, isooctyl, 2-ethylhexyl, n-nonyl, isononyl, n-decyl and isodecyl.
If one or more of the radicals R.sup.4 to R.sup.8 are C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -acyl, C.sub.1 -C.sub.18 -alkoxy or C.sub.1 -C.sub.12 -alkoxycarbonyl, the alkyl radicals therein can be, for example, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, n-hexyl, n-heptyl, n-octyl or 2-ethylhexyl.
Examples of suitable longer-chain alkyl radicals in C.sub.1 -C.sub.18 -alkoxy and C.sub.1 -C.sub.12 -alkoxycarbonyl groups are nonyl, 2-methylnonyl, isononyl, 2-methyloctyl, decyl, isod
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patent: 3215725 (1965-11-01), Strobel et al.
Organikum Organisch-Chemisches Grundpraktikum, 15.sup.th Edition, 1977.
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Chemical Abstracts, vol. 79, No. 21, Nov. 26, 1973.
Patent Abstracts of Japan, vol. 13, No. 494 (C-651), 8 Nov. 1989.
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Aumuller Alexander
Holderbaum Martin
Krause Alfred
Sperling Karin
Trauth Hubert
BASF - Aktiengesellschaft
Richter Johann
Sackey Ebenezer O.
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