Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...
Patent
1994-06-03
1995-07-18
Chang, Ceila
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Processes of preparing a desired or intentional composition...
524 99, 524102, 546188, 546216, 546223, 546224, 546242, 546246, 546247, C08K 53435, C07D21146, C07D21158
Patent
active
054342023
DESCRIPTION:
BRIEF SUMMARY
This application is a 35 U.S.C. .sctn. 371 filing of PCT/EP92/02733 filed Nov. 27, 1992.
The present invention relates to novel N-(.beta.-carbonyl- and .beta.-cyanovinyl)-2,2,6,6-tetramethylpiperidine derivatives of the formula I ##STR2## where R.sup.1 is COOR.sup.3, COR.sup.4, CONR.sup.4 R.sup.5 or CN, hydrogen, C.sub.3 -C.sub.5 -alkenyl or phenyl which can be mono- to trisubstituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, halogen, hydroxyl, phenoxy, phenyl, tolyl or xylyl, -C.sub.8 -cycloalkyl or phenyl which can be mono- to trisubstituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, halogen, hydroxyl, phenoxy, phenyl, tolyl or xylyl, ##STR3## --O--CO--, --O--CO--O--, --O--CO--NR.sup.6 -- or --NR.sup.6 --CO--NR.sup.6, where the linkage to position 4 of the piperidine ring takes place via an N or 0 in the stated group and -cycloalkyl, C.sub.7 -C.sub.20 -phenylalkyl or phenyl which can be mono- to trisubstituted by C.sub.1 -C.sub.4 -alkyl, halogen, phenyl or hydroxyl, more non-adjacent oxygens, C.sub.2 -C.sub.12 -hydroxyalkyl, C.sub.1 -C.sub.12 -haloalkyl, C.sub.3 -C.sub.5 -epoxyalkyl, C.sub.2 -C.sub.20 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.5 -C.sub.8 -cycloalkyl, C.sub.7 -C.sub.20 -Phenylalkyl, phenyl which can be mono- to trisubstituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, halogen or hydroxyl or is --CH.dbd.CH--COOR.sup.3 or C.sub.4 -C.sub.30 -alkyl which contains a heterocycle from the group comprising furan, tetrahydro furan, thiophene, imidazole, pyridine, piperidine, morpholine and .alpha.-piperidone as bridge or end group, or ##STR4## the case n=2 X has the same meanings as for the case n=1, non-adjacent oxygens or --NR.sup.7 -- groups, or is C.sub.5 -C.sub.8 -cycloalkylene, C.sub.7 -C.sub.20 -phenylalkylene, o-, m- or p-phenylene which can be mono- to trisubstituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, halogen or hydroxyl, or is C.sub.4 -C.sub.30 -alkylene which contains a heterocycle from the group comprising furan, tetrahydrofuran, thiophene, imidazole, pyridine, piperidine, morpholine and .alpha.-piperidone as bridge, where ##STR5## the case n=3 X.sub.3 A is ##STR6## and for the case n=4 ##STR7##
The present invention also relates to organic material stabilized against the action of light, oxygen and heat using the compounds I, especially stabilized synthetic materials and surface coatings.
Organic material, especially synthetic materials and surface coatings, is known to be very rapidly decomposed, especially by the action of light. This decomposition normally becomes manifest by yellowing, discoloration, fissuring or embrittlement of the material. The aim of stabilizers is therefore to protect organic material satisfactorily against decomposition by light, oxygen and heat.
Thus, EP-A 389 419 (1) recommends polyalkylpiperidine derivatives which have a hydrocarbyloxy group on the piperidine nitrogen, and thus have a lower basicity than, for example, N-alkyl-substituted polyalkylpiperidine derivatives, as light stabilizers in high molecular weight compounds.
Prior art agents of this type are still often unsatisfactory owing to the low compatibility with synthetic materials, the short duration of the protective action, the intrinsic color of the substances, the tendency to volatility and the thermal decomposition of the stabilizers on incorporation at elevated temperature.
It is an object of the present invention to provide stabilizers which provide more effective protection for organic material.
We have found that this object is achieved by the N-(.beta.-carbonyl- and .beta.-cyanovinyl)-2,2,6,6-tetramethylpiperidine derivatives I defined at the outset.
R.sup.1 is preferably COOR.sup.3.
R.sup.2 is preferably COOR.sup.3 or hydrogen.
R.sup.3 is preferably C.sub.1 -C.sub.4 -alkyl, especially methyl or ethyl.
The value of n is preferably 1 or 2.
When n=1 and n=2, X is preferably oxygen or --NR.sup.6 --, --NR.sup.6 --CO--, ##STR8## or --O--CO--, where R.sup.6
REFERENCES:
patent: 4360675 (1982-11-01), Nikles
patent: 4898946 (1990-02-01), Costanzi
patent: 5290940 (1994-03-01), Cunkle
Synthesis of 4-Piperidone Derivatives and Study of Their Pharmacological Properties, 1988 Plenum Publishing Corporation pp. 411-417 (1988).
Aumueller Alexander
Krause Alfred
Trauth Hubert
BASF - Aktiengesellschaft
Chang Ceila
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