Ciba-geigy Corporation

Ciba-geigy S.p.a.

Chimosa Chimica Organica S.p.a.

Ciba-geigy Corproation

Giuseppe Cantatore

Valerio Borzatta

Franca Masina

Paolo Cassandrini

Graziano Vignali

Compounds containing substituted piperidine groups, of the general formula (I) ##STR1## in which n is e.g. 1, 2 or 3, R.sub.1 is e.g. hydrogen or methyl, R.sub.2 is e.g. ethylene or trimethylene and if n is 1, A is e.g. hydrogen, --COOC.sub.18 H.sub.37 --n or --COC.sub.11 H.sub.23 --n, if n is 2, A is e.g. ##STR2## and if n is 3, A is e.g. ##STR3## are effective stabilizers for organic materials, especially synthetic polymers, which are subject to the action of light, heat and oxidation.

Compounds containing substituted piperidine groups for use as

The present invention relates to novel piperidine-triazine compounds of the general formula (I) ##STR1## in which R.sub.1 is e.g. methyl, acetyl or (C.sub.1 -C.sub.2 alkoxy)carbonyl, A is e.g. a group of the formula (IIa), ##STR2## in which R.sub.3 is e.g. hydrogen, methyl, 2,2,6,6-tetramethyl-4-piperidyl, 1,2,2,6,6-pentamethyl-4-piperidyl or 1-acetyl-2,2,6,6-tetramethyl-4-piperidyl, R.sub.4 is e.g. C.sub.3 -C.sub.6 alkylene, R.sub.2 is e.g. a group R.sub.1 -A- and n is e.g. a number from 1 to 5. The said compounds are effective as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials.

Piperidine-triazine compounds for use as stabilizers for organic

The present invention relates to novel piperidine-triazine compounds containing silane groups of the formula (I) ##STR1## in which R.sub.1 is a group of the formula ##STR2## R.sub.7 is e.g. hydrogen, X is e.g. &gt;N--R.sub.10 with R.sub.10 being C.sub.1 -C.sub.4 alkyl, R.sub.8 is e.g. a group of the formula ##STR3## with R.sub.11 being hydrogen and Z being as defined for X; Y is e.g. &gt;NH, R.sub.9 is e.g. trimethylene, R.sub.2 is e.g. methyl, ethoxy or OH, R.sub.3 and R.sub.4 are e.g. C.sub.1-C.sub.6 alkyl or phenyl, m+n is a number from 1 to 100, n is zero or a number from 1 to 90 and can vary from zero to 90% of the sum of m+n, R.sub.5 is e.g. ethyl and R.sub.6 is e.g. ethoxy, and, when m+n is a number from 3 to 10, R.sub.5 and R.sub.6 together can also form a direct bond. These compounds are effective as stabilizers for organic materials.

Piperidine-triazine compounds containing silane groups

The novel compounds of the formula (I) ##STR1## in which R.sub.1 is di(C.sub.1 -C.sub.4 -alkyl)amino, C.sub.1 -C.sub.4 -alkoxy, a 5-membered to 7-membered nitrogen containing heterocyclic group with the nitrogen atom bonded to the triazine ring, or a group of the formula (II), ##STR2## R.sub.2 and R.sub.4 which are identical or different are C.sub.1 -C.sub.12 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl, benzyl or 1,2,2,6,6-pentamethyl-4-piperidyl, n is 2 or 3 and, if n is 2, R.sub.3 is a group ##STR3## with R.sub.5 and R.sub.7, which are identical or different, being hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl, benzyl or 1,2,2,6,6-pentamethyl-4-piperidyl and R.sub.6 being C.sub.2 -C.sub.12 -alkylene, cyclohexylene, cyclohexylenedimethylene or methylenedicyclohexylene, or R.sub.3 is the divalent radical or a 6-membered to 7-membered heterocyclic compound with two nitrogen atoms which are each bonded to a triazine ring, or, if n is 3, R.sub.3 is a group ##STR4## with R.sub.8 and R.sub.11, which are identical or different, being as defined above for R.sub.5 and R.sub.7, and R.sub.9 and R.sub.10, which are identical or different, being C.sub.2 -C.sub.12 -alkylene, are useful as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials.

Piperidylaminotriazine derivatives and their use as stabilizers

Piperidine-triazine compounds of the general formula (I) ##STR1## in which R.sub.1 is e.g. hydrogen or methyl, R.sub.2 is e.g. C.sub.2 -C.sub.6 alkylene, R.sub.3 is e.g. a group ##STR2## ##STR3## can be used as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials, in particular synthetic polymers.

The new compounds of formula (I) ##STR1## in which R.sub.1 is e.g. hydrogen or methyl, R.sub.2 is e.g. a group --OR.sub.5 or ##STR2## in which R.sub.5 is e.g. 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl, R.sub.6 and R.sub.7 which are identical or different are e.g. C.sub.1 -C.sub.8 alkyl, tetrahydrofurfuryl, 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl, or R.sub.6 is also hydrogen, or the group ##STR3## is e.g. 4-morpholinyl, R.sub.3 and R.sub.4 which are identical or different are e.g. hydrogen, methyl, 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl, m and n are e.g. 3, and X is e.g. --O-- or ##STR4## where R.sub.9 is C.sub.1 -C.sub.8 alkyl, tetrahydrofurfuryl, 2,2,6,6-tetramethyl-4-piperidyl or 1,2,2,6,6-pentamethyl-4-piperidyl, are effective as light stabilizer, heat stabilizers and oxidation stabilizers for organic materials, in particular synthetic polymers.

Compounds of formula (I) ##STR1## in which R.sub.1 is hydrogen, O.degree., CN, NO, cyanomethyl, C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.12 -alkenyl or C.sub.3 -C.sub.12 -alkynyl subject to the proviso that the carbon atom attached to the nitrogen atom is a primary carbon atom, C.sub.7 -C.sub.12 -aralkyl, C.sub.1 -C.sub.12 -acyl, 2,3-epoxypropyl, OH-monosubstituted C.sub.2 -C.sub.6 -alkyl or 2,3-dihydroxypropyl, R.sub.2 is hydrogen, C.sub.1 -C.sub.18 -alkyl, C.sub.5 -C.sub.18 -cycloalkyl, C.sub.6 -C.sub.18 -aryl or C.sub.7 -C.sub.18 -aryalkyl, R.sub.3 is C.sub.6 -C.sub.18 -aryl or a group of the formula (II) ##STR2## in which R.sub.1 is as defined above, n is an integer from 1 to 4 and R.sub.4 is an organic or inorganic radical of a valency equal to n are useful for stabilizing organic material against oxidative, thermal and/or light induced degradation.

Piperidine compounds and their use as stabilizers

The novel compounds of the formula (I) ##STR1## in which n is 1 or 2, R.sub.1 is hydrogen, O.multidot., OH, NO, CH.sub.2 CN, C.sub.1 -C.sub.8 -alkyl, allyl, benzyl, hydroxyalkyl, alkoxy, cycloalkoxy or acyl, R.sub.2 is alkyl, cycloalkyl, phenylalkyl, alkoxyalkyl, tetrahydrofurfuryl or a group of the formula (II) and A is a monovalent or divalent moiety, in which R.sub.1 is as defined above, and, if n=1, A is a group of the formula (III) in which each R.sub.9 independently is hydrogen or methyl, r is zero or 1 and are useful as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials.

Piperidine compounds for use as light stabilizers, heat stabilizers and

Novel piperidine compounds of the general formula (I) ##STR1## in which m is an integer from 1 to 4, R.sub.1 and R.sub.2 are as defined in claim 1 and at least one 2,2,6,6-tetramethylpiperidinyl group, being present in R.sub.1 or R.sub.2 are useful as light stabilizers, heat stabilizers and oxidation stabilizers for organic material, especially for synthetic polymers.

Novel piperidine compounds

The novel compounds of the formula (I) ##STR1## in which R.sub.1 is di(C.sub.1 -C.sub.4 -alkyl)amino, C.sub.1 -C.sub.4 -alkoxy, a 5-membered to 7-membered nitrogen containing heterocyclic group with the nitrogen atom bonded to the triazine ring, or a group of the formula (II), ##STR2## R.sub.2 and R.sub.4 which are identical or different are C.sub.1 -C.sub.12 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl, benzyl or 1,2,2,6,6-pentamethyl-4-piperidyl, n is 2 or 3 and, if n is 2, R.sub.3 is a group ##STR3## with R.sub.5 and R.sub.7, which are identical or different, being hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl, benzyl or 1,2,2,6,6-pentamethyl-4-piperidyl and R.sub.6 being C.sub.2 -C.sub.12 -alkylene, cyclohexylene, cyclohexylenedimethylene or methylenedicyclohexylene, or R.sub.3 is the divalent radical of a 6-membered to 7-membered heterocyclic compound with two nitrogen atoms which are each bonded to a triazine ring, or, if n is 3, R.sub.3 is a group ##STR4## with R.sub.8 and R.sub.11, which are identical or different, being as defined above for R.sub.5 and R.sub.7, and R.sub.9 and R.sub.10, which are identical or different, being C.sub.2 -C.sub.12 -alkylene, are useful as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials.

The compounds of the formula (I) ##STR1## in which R.sub.1 is C.sub.1 -C.sub.8 -alkyloxy, allyloxy, allylamino, di(C.sub.1 -C.sub.4 -alkyl)-amino, diallylamino, a 5-membered to 7-membered nitrogen containing heterocyclic group with the nitrogen atom linked to the triazine ring, or a group of the formula (II), ##STR2## R.sub.2 is hydrogen, O, OH, NO, CH.sub.2 CN, C.sub.1 -C.sub.8 -alkyl, allyl, benzyl, C.sub.1 -C.sub.8 -acyl, C.sub.1 -C.sub.18 -alkyloxy, C.sub.5 -C.sub.12 -cycloalkyloxy or OH-monosubstituted C.sub.2 -C.sub.4 -alkyl, R.sub.3 and R.sub.5 independently are hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.5 -C.sub.12 -cycloalkyl, C.sub.7 -C.sub.9 -phenylalkyl, tetrahydrofurfuryl, C.sub.2 -C.sub.4 -alkyl monosubstituted by OH, by C.sub.1 -C.sub.4 -alkyloxy or by di(C.sub.1 -C.sub.4 -alkyl)amino, or a group of the formula (III) ##STR3## with R.sub.2 as defined above, R.sub.4 is hydrogen, C.sub.1 -C.sub.12 -alkyl or cyclohexyl and n is an integer from 2 to 6, are useful as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials, in particular synthetic polymers.

Polytriazine compounds having a number average molecular weight from 1000 to 20,000 and containing recurring piperidylamidinotriazine structural units of the formula (IA) ##STR1## or a combination of said structural units of the formula (IA) with recurring structural units of the formula (IB)

Polytriazine compounds containing recurring piperidylamidinotriazine

A compound selected from the group consisting of compounds of the formula (I) ##STR1## The compounds of the formula (I) are useful as light stabilizers, heat stabilizers, and oxidation stabilizers.

Triazine compounds derived from 2,2,6,6-tetramethylpiperidine

The present invention relates to novel bis-piperidyl-triazine compounds with 2 or more triazine rings, to their use as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials, in particular synthetic polymers, and to the organic materials thus stabilized.

Polyamines partially substituted by bis-piperidyl-triazines

Compounds of formula (I) ##STR1## in which R.sub.1 is hydrogen, O.sup.., CN, NO, cyanomethyl, C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.12 -alkenyl or C.sub.3 -C.sub.12 -alkynyl subject to the proviso that the carbon atom attached to the nitrogen atom is a primary carbon atom, C.sub.7 -C.sub.12 -aralkyl, C.sub.1 -C.sub.12 -acyl, 2,3-epoxypropyl, OH-monosubstituted C.sub.2 -C.sub.6 -alkyl or 2,3-dihydroxypropyl, R.sub.2 is hydrogen, C.sub.1 -C.sub.18 -alkyl, C.sub.5 -C.sub.18 -cycloalkyl, C.sub.6 -C.sub.18 -aryl or C.sub.7 -C.sub.18 -aralkyl, R.sub.3 is C.sub.6 -C.sub.18 -aryl or a group of the formula (II) ##STR2## in which R.sub.1 is as defined above, n is an integer from 1 to 4 and R.sub.4 is an organic or inorganic radical of a valency equal to n are useful for stabilizing organic material against oxidative, thermal and/or light induced degradation.

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Bitonto, Italy

Giuseppe Cantatore