Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1994-05-31
1996-04-02
Wu, Shean C.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
546186, 544360, 544100, 544102, 544103, C07D21100, C07D40100, C08K 534
Patent
active
055042112
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel polyalkyl-piperidinyl-containing .beta.-aminoacrylic ester derivatives of the general formula I ##STR2## where n is from 1 to 50, C.sub.1 -C.sub.6 -alkyl, formyl, C.sub.2 -C.sub.6 -alkanoyl, C.sub.1 -C.sub.12 -alkoxy, C.sub.5 -C.sub.6 -cycloalkoxy, cyanomethyl, 2-hydroxyethyl, benzyl or a radical of the formula --CR.sup.3 .dbd.CH--CO--OR.sup.4, and --CO--OR.sup.4 and -C.sub.18 -aralkyl, phenyl or tolyl, phenylene, biphenylene or a radical of the formula ##STR3## wherein m is 2 or 3, and when n=1 -alkanoyl, C.sub.7 -C.sub.18 -aralkyl or a group of the formula --CH.dbd.CH--CO--O--Z , -C.sub.18 -aralkyl, phenyl, tolyl or a radical of the formula --(CH.sub.2 CH.sub.2 O).sub.p H or -- CH(CH.sub.3)CH.sub.2 O!.sub.p H, wherein p is from 1 to 30, and --CH.dbd.CH--CO--O--X--O--CO--C.tbd.CH Z is bonded through the C--C double bond in B, phenylene, biphenylene or a group of the formula --(CH.sub.2 CH.sub.2 O).sub.q CH.sub.2 CH.sub.2 -- or -- CH(CH.sub.3)CH.sub.2 O!.sub.q CH(CH.sub.3)CH.sub.2 --, wherein q is from 1 to 30, and ##STR4##
The present invention further relates to organic material, in particular plastics and paints, stabilized against the action of light, oxygen and heat with the compounds I.
Organic material, in particular plastics and paints, is known to be destroyed very rapidly, in particular by the action of light. This destruction customarily takes the form of yellowing, discoloring, cracking or embrittlement of the material. Stabilizers are therefore used to give satisfactory protection from destruction of organic material by light, oxygen and heat.
For instance, EP-A-213 570 describes compounds in which two polyalkylpiperidine groups are linked by a glycoluril bridge via an exocyclic nitrogen atom in the 4-position. These compounds can also exist in polymeric form. They are recommended for use as stabilizers for organic material, in particular for plastics.
What is frequently unsatisfactory with these prior art agents is their low compatibility with plastics, the short duration of their protective effect, their self-color, their volatility and their thermal decomposition when being incorporated at elevated temperatures.
It is an object of the present invention to provide UV absorbers and stabilizers which provide more effective protection of organic material.
We have found that this object is achieved by the polyalkylpiperidinyl-containing .beta.-aminoacrylic ester derivatives I defined at the beginning.
The variable n is preferably from 1 to 10, in particular 1.
R.sup.1 and R.sup. 2 are each preferably hydrogen, methyl or a radical of the formula --CH.dbd.CH--CO--OR.sup.5, wherein R.sup.5 is C.sub.1 -C.sub.4 -alkyl. Here R.sup.1 and R.sup.2 are identical or different.
The variable A is preferably a group of the formula --(CH.sub.2).sub.k --, wherein k is from 2 to 12, in particular from 2 to 8.
Very particular preference is give to .beta.-aminoacrylic ester derivatives of the general formula Ia ##STR5## where R.sup.1, R.sup.2 and A are each as defined above and R.sup.5 is C.sub.1 -C.sub.4 -alkyl.
Examples of suitable straight-chain or branched alkyl radicals for R.sup.1 to R.sup.5, Y and Z, described as C.sub.1 -C.sub.4 --, C.sub.1 -C.sub.6 - and C.sub.1 -C.sub.18 -alkyl radicals, are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-amyl, isoamyl, sec-amyl, tert-amyl, neopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, isononyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, isotridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl and n-octadecyl. Preference is given in general to lower alkyl radicals, in particular C.sub.1 -C.sub.4 -alkyl radicals, especially methyl and ethyl.
As straight-chain or branched alkanoyl for R.sup.1 and R.sup.2 and for Y, described as C.sub.2 -C.sub.6 - and C.sub.2 -C.sub.18 -alkanoyl, it is possible to use in particular acetyl, but also propionyl, butyryl, isobutyryl, pentanoyl, hexanoyl, heptanoyl, octanoyl, 2-ethylhexanoyl, decanoyl, dodecanoyl, tetradecanoyl, hexadecanoyl and octa
REFERENCES:
patent: 4468488 (1984-08-01), Minegawa et al.
patent: 4769457 (1988-09-01), Helwig et al.
Aumueller Alexander
Krause Alfred
Trauth Hubert
BASF - Aktiengesellschaft
Wu Shean C.
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