Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Nitrogen-containing reactant
Patent
1995-08-07
1997-09-23
Seidleck, James J.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Nitrogen-containing reactant
544180, 544215, 544216, C08G 7306
Patent
active
056706138
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP 94/00182 filed Jan. 25, 1994.
The present invention relates to novel N-vinyl-containing glycoluril derivatives of the general formula I ##STR2## where R.sup.1 and R.sup.2 independently of one another are each hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.5 -C.sub.8 -cycloalkyl, phenyl, tolyl or C.sub.7 -C.sub.12 -phenylalkyl or formula COOR.sup.9, tolyl or C.sub.7 -C.sub.12 -phenylalkyl.
The present invention furthermore relates to a process for the preparation of the compounds I and their use as light stabilizers and stabilizers for organic material, in particular for plastics and coatings, and to organic material stabilized with the compounds I against the action of light, oxygen and heat, in particular stabilized plastics and coatings.
Organic material, in particular plastics and coatings, is known to be destroyed very rapidly, especially by the action of light. This destruction is usually evident in the form of yellowing, discoloration, cracking or embrittlement of the material. With light stabilizers and stabilizers, it is therefore intended to achieve satisfactory protection against the destruction of organic material by light, oxygen and heat.
For example, EP-B 213 570 discloses glycoluril derivatives which are similar to those of the present invention, except that the compounds described there have only hydrogen, chlorine, bromine, hydroxyl, alkoxy, carboxyl, carboxylic ester or unsubstituted or substituted carbamoyl as substituents at the piperidine nitrogen atoms. These compounds are also suitable as stabilizers for organic material.
Such prior art agents are frequently unsatisfactory with regard to their compatibility with plastics, the duration of their protective action, their natural color and their tendency to volatility and thermal decomposition during incorporation at elevated temperatures into the material to be stabilized.
It is an object of the present invention to provide light stabilizers and stabilizers which provide even more effective protection for organic material.
We have found that this object is achieved by the N-vinyl-containing glycoluril derivatives I defined at the outset.
Examples of suitable straight-chain or branched alkyl radicals R.sup.1 to R.sup.7 and R.sup.9, which are mentioned as C.sub.1 -C.sub.4 -alkyl radicals, C.sub.1 -C.sub.8 -alkyl radicals and C.sub.1 -C.sub.12 -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 and n-dodecyl. Lower alkyl radicals are generally preferred, especially C.sub.1 -C.sub.4 -alkyl, in particular methyl and ethyl.
Particularly suitable C.sub.5 -C.sub.8 -cycloalkyl radicals R.sup.1, R.sup.2 and R.sup.9 are cyclopentyl and cyclohexyl, as well as cycloheptyl, cyclooctyl, methylcyclopentyl, dimethylcyclopentyl, methylcyclohexyl, ethylcyclohexyl and dimethylcyclohexyl.
Examples of suitable C.sub.7 -C.sub.12 -phenylalkyl radicals R.sup.1, R.sup.2 and R.sup.9 are 1-phenylethyl, 2-phenylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl, 2-phenylprop-2-yl, 4-phenylbutyl, 2,2-dimethyl-2-phenylethyl, 5-phenylamyl, 6-phenylhexyl and especially benzyl.
Suitable tolyl radicals are ortho-, meta- and especially para-tolyl.
In a preferred embodiment, R.sup.1 and R.sup.2 are each hydrogen, methyl, ethyl, phenyl, tolyl or benzyl, among which hydrogen is very particularly preferred.
In a further preferred embodiment, R.sup.3 to R.sup.6 are each methyl.
In a further preferred embodiment, R.sup.7 is hydrogen, methyl, ethyl, carboxymethyl or carboxyethyl, in particular hydrogen.
In a further preferred embodiment, R.sup.8 is carboxymethyl or in particular carboxyethyl.
There are in principle no restrictions regarding the three-dimensional position of the radical R.sup.8 at the double bond of I relative to the piperidine ring and to R.sup.7. Both E and Z isomers and, where R.sup.7 is H, both the cis and the trans isomers may be present. Mixtures of t
REFERENCES:
patent: 4769457 (1988-09-01), Helwig et al.
Aumueller Alexander
Korona Eckhard
Krause Alfred
Trauth Hubert
BASF - Aktiengesellschaft
Seidleck James J.
Truong Duc
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