Ciba-geigy Corporation

Roberto Scrima

Valerio Borzatta

Graziano Zagnoni

Graziano Vignali

Roland A Winter

James Peter Galbo

Primo Carrozza

Fabrizio Guizzardi

Michael H Ackerman

Giampiero Vessa

Novel process for the preparation of 2,2,6,6-tetramethyl-4-piperidyloxy-1,3,5-triazines, based on the reaction of cyanuric chloride with C.sub.1 -C.sub.4 alkanols or with sodium or potassium C.sub.1 -C.sub.4 alkoxides and subsequent reaction with 2,2,6,6-tetramethyl-4-piperidinols in the presence of a transesterification catalyst. The various reactions can be carried out in the same reactor, without isolation of the intermediates. ##STR1##

Process for the preparation of

Compounds of the formula (I) ##STR1## in which n is zero or 1, X denotes a group of formula (II), ##STR2## R.sub.1 and R.sub.5 are e.g. hydrogen, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, are C.sub.2 -C.sub.12 alkylene, R.sub.6 is e.g. hydrogen or C.sub.1 -C.sub.18 alkyl and R.sub.7 is e.g. hydrogen or C.sub.1 -C.sub.8 alkyl, are useful as stabilizers for organic materials against degradation induced by light, heat or oxidation.

2,2,6,6-tetramethylpiperidine derivatives for use as stabilizing agents

The present invention relates to novel piperidine compounds of the formula (I) V5 V pV ##STR1## in which R.sub.1, R.sub.2 and R.sub.3 are as defined in the text. The compounds of the invention can be used as fight stabilizers, heat stabilizers and oxidation stabilizers for organic materials, in particular synthetic polymers.

Derivatives of 2,2,6,6-tetramethyl-4-piperidinol for use as light

The present invention relates to novel piperidine compounds of the formula (I) ##STR1## in which X.sub.1, X.sub.2, X.sub.3 and n are as defined in the text. The compounds of the invention can be used as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials, in particular synthetic polymers.

Piperidine compounds for use as stabilizers for organic materials

The present invention relates to synergistic mixtures for stabilising polymeric organic materials against light, heat and oxidation; said synergistic mixtures contain sterically hindered cyclic amines and particular derivatives of 3-pyrazolidinone or 1,2,4-triazolidine-3,5-dione. In addition, the present invention relates to some new derivatives of 3-pyrazolidinone or 1,2,4-triazolidine-3,5-dione.

Stabilization of polymeric organic materials by using synergistic

The present invention relates to novel piperidine compounds of the formula (I) and to their use as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials. The definitions of R.sub.1, R.sub.2 and R.sub.3 are given in the text. ##STR1##

Polyalkyl-4-piperidinol derivatives for use as stabilizers for organic

Novel piperidine compounds of the formula (I) ##STR1## in which R.sub.1 is e.g. hydrogen or methyl, n is e.g. 1 and A is e.g. --COR.sub.2 with R.sub.2 being C.sub.1 -C.sub.18 alkyl. The said compounds are effective as light stabilisers, heat stabilizers and oxidation stabilisers for organic materials.

Tetramethylpiperidine compounds for use as stabilizers for organic

The present invention relates to novel tetramethylpiperidine compounds of the general formula (I) ##STR1## in which X and Y are e.g. a group of the formula (IIa) or (IIb) ##STR2## in which R.sub.1 and R.sub.2 are e.g. hydrogen or methyl. The said compounds are effective stabilizers for organic materials, in particular synthetic polymers, against the action of light, heat and oxidation.

Piperidine compounds a tetrahydrofuran ring for use as stabilisers for

The present invention relates to novel piperidine-triazine compounds of the formula (I) ##STR1## in which R.sub.1 is e.g. hydrogen or methyl, A.sub.1 is e.g. &gt;N--CH.sub.3, R.sub.2 is e.g. --(CH.sub. 2).sub.2-6 --, R.sub.3 is e.g. 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl, or --A.sub.1 --R.sub.2 -- is a direct bond and, in this case, R.sub.3 is e.g. a group ##STR2## is a group of the formula (IVa) or (IVc) ##STR3## q and m are e.g. zero, X.sub.1 is e.g. a group of the formula (Va)

Piperidine-triazine compounds for use as stabilizers for organic

The present invention relates to novel piperidine-triazine compounds of the general formula (I) ##STR1## in which R.sub.1 is e.g. hydrogen or methyl, A is e.g. --O--, m is e.g. 3, R.sub.2 is e.g. a group --OR.sub.4 or ##STR2## R.sub.4 is e.g. C.sub.1 -C.sub.4 alkyl, 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl, R.sub.5 and R.sub.6 which can be identical or different are e.g. C.sub.1 -C.sub.8 alkyl, cyclohexyl, tetrahydrofurfuryl, a group ##STR3## 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl, or R.sub.5 can also be hydrogen, or ##STR4## is e.g. 4-morpholinyl, n is 1, 2, 3 or 4 and, if n is 1, R.sub.3 is e.g. as defined above for R.sub.2 and, if n is 2, R.sub.3 is e.g. a group --E.sub.1 --R.sub.8 --E.sub.2 -- in which E.sub.1 and E.sub.2 which can be identical or different are e.g. &gt;N-R.sub.12, R.sub.8 is e.g. C.sub.2 -C.sub.6 alkylene, C.sub.8 -C.sub.10 alkylene interrupted by 2 or 3 oxygen atoms or methylenedicyclohexylene and R.sub.12 is e.g. hydrogen, methyl, 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl, and, if n is 3, R.sub.3 is e.g. a group ##STR5## in which R.sub.12 is e.g. as defined above and R.sub.13 and R.sub.14 which can be identical or different are e.g. C.sub.2 -C.sub.3 alkylene, and, if n is 4, R.sub.3 is e.g. a group ##STR6## in which R.sub.12 is e.g. as defined above and R.sub.20 and R.sub.21 which can be identical or different are e.g. C.sub.2 -C.sub.3 alkylene. These compounds are effective as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials.

The compounds of formula VIIIa-1 ##STR1## where R.sub.1 is hydrogen, alkyl, O.sup.., OH, NO, CH.sub.2 CN, alkoxy, cycloalkoxy, alkenyl, phenylalkyl, alkanoyl, alkenoyl or benzoyl, are valuable intermediates for the preparation of selected hindered amine light stabilizers.

Tri-piperdine compounds as stabilizers for organic materials

The present invention relates to a novel method for stabilizing synthetic thermoplastic materials against thermal degradation, which comprises incorporating in said materials one or more compounds of the formula (I) ##STR1## in which R.sub.1 is unsubstituted or substituted phenyl, n is e.g. 1, 2 or 3, and, when n is 1, R.sub.2 is e.g. --COR.sub.3, --COOR.sub.4 or --CO-N(R.sub.5)R.sub.6 in which R.sub.3 is e.g. C.sub.4 -C.sub.17 alkyl, R.sub.4 is e.g. C.sub.4 -C.sub.18 alkyl, cyclohexyl or t-butylcyclohexyl, R.sub.5 and R.sub.6 which can be identical or different are e.g. C.sub.2 -C.sub.8 alkyl or cyclohexyl, and, when n is 2, R.sub.2 is e.g. --CO--R.sub.10 --OC, --COO-R.sub.11 --OOC-- or --CONH--R.sub.12 --NHCO- in which R.sub.10 is e.g. C.sub.2 -C.sub.8 alkylene, R.sub.11 is e.g. C.sub.4 -C.sub.6 alkylene and R.sub.12 is e.g. C.sub.4 -C.sub.6 alkylene, and, when n is 3, R.sub.2 is e.g. benzenetricarbonyl. Several compounds of the formula (I) are new.

Method for stabilizing synthetic thermoplastic materials against thermal

The present invention relates to polymeric thermoplastic materials stabilized against thermal degradation by means of using one or more compounds of the formula (I) ##STR1## in which R.sub.1 is e.g. C.sub.1 -C.sub.4 alkyl or phenyl and n is e.g. 1 or 2 and, when n is 1, R.sub.2 is e.g. C.sub.1 -C.sub.4 alkyl, phenyl or cyclohexyl, and, when n is 2, R.sub.2 is e.g. C.sub.2 -C.sub.6 alkylene, methylenedicyclohexylene, a group ##STR2## methylphenylene or methylenediphenylene.

Polymeric thermoplastic materials, comprising

Compounds of formula I ##STR1## wherein R.sub.1 is hydrogen, alkyl or alkoxy, --A.sub.1 --R.sub.2 --N(R.sub.3)-- and --X.sub.1 --(X.sub.2 --X.sub.3).sub.m -- are selected linking groups, Y.sub.1 and Y.sub.2 are selected terminal moieties and n is 1 to 50, are effective light, heat and oxidation stabilizers for a variety of organic materials.

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Bologna, Italy

Roberto Scrima