Piperidine-triazine compounds suitable for use as stabilisers for organic materials
AssigneeCiba-Geigy Corporation
InventorsValerio Borzatta, Graziano Vignali, Fabrizio Guizzardi
Life of this patent
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Abstract
Novel piperidine-triazine compounds of the formula (Ia) and (Ib) suitable for use as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials. The meanings of R.sub.1, R.sub.2, R.sub.3, G.sub.1, G.sub.2, L.sub.1, L.sub.2, m and n are defined in the text. ##STR1##
Claims6
A compound of formula (Ia) ##STR114## in which R.sub.1 is hydrogen, C.sub.1 -C.sub.8 alkyl, O., OH, CH.sub.2 CN, C.sub.1 -C.sub.18 alkoxy, C.sub.5 -C.sub.12 cycloalkoxy, C.sub.3 -C.sub.6 alkenyl, C.sub.7 -C.sub.9 phenylalkyl which is unsubstituted or substituted on the phenyl with 1, 2 or 3 C.sub.1 -C.sub.4 alkyls, aliphatic C.sub.1 -C.sub.8 acyl;
- R.sub.2 is ##STR115## where R.sub.4 is hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.12 cycloalkyl, which is unsubstituted or substituted with 1, 2 or 3 C.sub.1 -C.sub.4 alkyls, C.sub.7 -C.sub.7 phenylalkyl which is unsubstituted or substituted on the phenyl with 1, 2 or 3 C.sub.1 -C.sub.4 alkyls, tetrahydrofurfuryl, a group of formula (II) ##STR116## or C.sub.2 -C.sub.4 alkyl which is substituted in the 2, 3 or 4 position with C.sub.1 -C.sub.8 alkoxy, with di(C.sub.1 -C.sub.4 alkyl)amino or with a group of formula (III) ##STR117## where A.sub.1 is a direct bond, --O--, --CH.sub.2 --, --CH.sub.2 CH.sub.2 -- or ##STR118## or R.sub.2 is also one of the groups of formulae (IVa)-(IVc) ##STR119## in which R.sub.1 is as defined above, A.sub.2 is --CH.sub.2 CH.sub.2 --, --CO--, --COCO--, --CH.sub.2 CO-- or --COCH.sub.2 CO-- and p is zero or 1, the nitrogen atom substituted with the piperidyl group being bound to the triazine ring of formula (Ia) or (Ib);
- R.sub.3 is a group of formula (V) ##STR120## with R.sub.1 and R.sub.2 as defined above, or a group of formula (III) or an R.sub.5 O-- or ##STR121## group, where R.sub.5, R.sub.6 and R.sub.7, which are identical or different, are hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.12 cycloalkyl which is unsubstituted or substituted with 1, 2 or 3 C.sub.1 -C.sub.4 alkyls, C.sub.8 -C.sub.18 alkenyl, phenyl which is unsubstituted or substituted on the phenyl with 1, 2 or 3 C.sub.1 -C.sub.4 alkoxy, C.sub.7 -C.sub.9 phenylalkyl which is unsubstituted or substituted in the 2, 3 or 4 position with C.sub.1 -C.sub.8 alkoxy or with the di(C.sub.1 -C.sub.4 alkyl)amino or with a group of formula (III);
- G.sub.1 is a group of formula (VI) ##STR122## in which A.sub.3 is a >N--(R.sub.8 --A.sub.5).sub.q group, where R.sub.8 is C.sub.2 -C.sub.6 alkylene, A.sub.5 is --O-- or ##STR123## and q is zero or 1, with R.sub.10 having any one of the meanings given for R.sub.4, and A.sub.4 is --CH.sub.2 CH.sub.2 -- or a ##STR124## or ##STR125## group, the endocyclic nitrogen atom of the formula (VI) being able to be bound to the triazine ring or to the L.sub.1 group of formula (Ia);
- m is 1, 2, 3 or 4;
- if m is 1, L.sub.1 is hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.7 -C.sub.9 phenylalkyl which is unsubstituted or substituted on the phenyl with 1, 2 or 3 C.sub.1 -C.sub.4 alkyls, aliphatic, cycloaliphatic or aromatic acyl containing not more than 22 carbon atoms or (C.sub.1 -C.sub.18 alkoxy)carbonyl;
- if m is 2, L.sub.1 is C.sub.2 -C.sub.12 alkylene, C.sub.4 -C.sub.12 alkylene interrupted by 1, 2 or 3 oxygen atoms, phenylenedi(C.sub.1 -C.sub.4 alkylene), aliphatic, cycloaliphatic or aromatic diacyl containing not more than 20 carbon atoms or one of the groups of formulae (VIIIa)-(VIIId) ##STR126## in which R.sub.13 has any one of the meanings given for R.sub.3 or is a group of formula (IX) ##STR127## where R.sub.1, R.sub.2 and R.sub.3 are as defined above and R.sub.18 is a group of formula (VI) or a group of formula (VII) as defined above, or R.sub.13 is also an R.sub.18 H group, R.sub.14 has any one of the meanings given for R.sub.3 or is a group of formula (IX), R.sub.15 is a group of formula (Xa) or (Xb) ##STR128## in which A.sub.7, A.sub.8 and A.sub.9, which are identical or different, have any one of the meanings given for A.sub.5, R.sub.19 is C.sub.2 -C.sub.12 alkylene, C.sub.4 -C.sub.12 alkylene interrupted by 1,2 or 3 oxygen atoms, C.sub.5 -C.sub.7 cycloalkylene, C.sub.5 -C.sub.7 cycloalkylenedi(C.sub.1 -C.sub.4 alkylene), C.sub.1 -C.sub.4 alkylenedi(C.sub.5 -C.sub.7 cycloalkylene), phenylenedi(C.sub.1 -C.sub.4 -alkylene) or is C.sub.4 -C.sub.12 alkylene interrupted by an ##STR129## group, where R.sub.21 has any one of the meanings given for R.sub.4 or is an aliphatic, cycloaliphatic or aromatic acyl containing not more than 12 carbon atoms or (C.sub.1 -C.sub.12 alkoxy)carbonyl, C.sub.2 -C.sub.4 alkylidenedi(C.sub.5 -C.sub.7 cycloalkylene), phenylene or C.sub.2 -C.sub.4 alkylidenediphenylene, each phenylene group being unsubstituted or substituted with 1 or 2 C.sub.1 -C.sub.4 alkyls, or R.sub.19 is a ##STR130## group, with R.sub.22 being hydrogen or C.sub.1 -C.sub.4 alkyl, or a ##STR131## group, R.sub.20 and R.sub.23 are C.sub.2 -C.sub.6 alkylene, s is zero or 1, A.sub.10 has any one of the meanings given for A.sub.3, R.sub.16 and R.sub.17 are C.sub.2 -C.sub.12 alkylene, C.sub.4 -C.sub.12 alkylene interrupted by 1, 2 or 3 oxygen atoms, C.sub.5 -C.sub.7 cycloalkylene, C.sub.5 -C.sub.7 cycloalkylenedi(C.sub.1 -C.sub.4 alkylene), C.sub.1 -C.sub.4 alkylenedi(C.sub.5 -C.sub.7 cycloalkylene), phenylenedi(C.sub.1 -C.sub.4 alkylene), C.sub.2 -C.sub.4 alkylenedi(C.sub.5 -C.sub.7 cycloalkylene), phenylene or C.sub.2 -C.sub.4 alkylidenediphenylene, each phenylene group being unsubstituted or substituted with 1 or 2 C.sub.1 -C.sub.4 alkyls, and r is zero or 1;
- if m is 3, L.sub.1 is aliphatic, cycloaliphatic or aromatic triacyl containing not more than 12 carbon atoms or a group of formula (XIa) or (XIb) ##STR132## in which R.sub.24 is as defined above for R.sub.14 and R.sub.25 is one of the groups of formulae (XIIA)-(XIId) ##STR133## in which A.sub.11, A.sub.12 and A.sub.13, which are identical or different, have any one of the meanings given for A.sub.5, R.sub.26, R.sub.27 and R.sub.28, which are identical or different, are C.sub.2 -C.sub.6 alkylene, t is zero or 1, R.sub.29, R.sub.30, R.sub.31 and R.sub.32, which are identical or different, have any one of the meanings given for R.sub.4, A.sub.14 is a direct bond or --CH.sub.2 --, u and v, which are identical or different, are integers from 2 to 6 and R.sub.33 is C.sub.3 -C.sub.12 alkanetriyl;
- and
- if m is 4, L.sub.1 is aliphatic or aromatic tetraacyl containing not more than 12 carbon atoms, tetrahydrofuran-2,3,4,5-tetracarbonyl or a group of formula (XIII) ##STR134## in which R.sub.34 is as defined above for R.sub.14 and R.sub.35 is one of the groups of formulae (XIVa)-(XIVc) ##STR135## in which A.sub.15 has any one of the meanings given for A.sub.5, R.sub.36 and R.sub.37, which are identical or different, are C.sub.2 -C.sub.6 alkylene, x is zero or 1 and R.sub.38 is C.sub.4 -C.sub.12 alkanetetrayl.
Dependencies are inferred from the claim text.