US 5,844,026 AGranted

N,N',N''-tris{2,4-bisHydrocarbyloxy-2,2,6,6-tetra- methylpiperidin-4-yl)alkylamino!-s-triazin-6-yl}-3,3'-ethylenediiminodipr opylamines, their isomers and bridged derivatives and polymer compositions stabilized therewith

AssigneeCiba Specialty Chemicals Corporation

InventorsJames P. Galbo, Henry C. Grace, Douglas W. Horsey, Peter Solera, Rangarajan Srinivasan

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Abstract

A mixture of the compounds identified in the title, their pure isomers and alkane-bridged derivatives are particularly effective in stabilizing polymer compositions, particularly polyolefin compositions.

Claims32

Dependent claims

A composition stabilized against thermal, oxidative or light-induced degradation which comprises,

(a) an organic material subject to thermal, oxidative or light-induced degradation, and
(b) an effective stabilizing amount of a mixture of N,N',N"'-tris{2,4-bis(1-hydrocarbyloxy-2,2,6,6-tetramethylpiperidin-4-yl) alkylamino!-s-triazin-6-yl}-3,3'-ethylenediiminodipropylamine;
N,N',N"-tris{2,4-bis-(1-hydrocarbyloxy-2,2,6,6-tetramethylpiperidin-4-yl) alkylamino!-s-triazin-6-yl}-3,3'-ethylenediiminodipropylamine and bridged derivatives as described by formulas I, II, IIA and III
R.sub.1 NH--CH.sub.2 CH.sub.2 CH.sub.2 NR.sub.2 CH.sub.2 CH.sub.2 NR.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 NHR.sub.4 (I)
T--E.sub.1 --T.sub.1 (II)
T--E.sub.1 (IIA)
G--E.sub.1 --G.sub.1 --E.sub.1 --G.sub.2 (III)
where in the tetraamine of formula I,
R.sub.1 and R.sub.2 are the s-triazine moiety E;
and one of R.sub.3 and R.sub.4 is the s-triazine moiety E with the other of R.sub.3 and R.sub.4 being hydrogen,
E is ##STR3## R is methyl, cyclohexyl or octyl, R.sub.5 is alkyl of 1 to 12 carbon atoms,
where in the compound of formula II or IIA when R is cyclohexyl or octyl
T and T.sub.1 are each a tetraamine substituted by R.sub.1 -R.sub.4 as defined for formula I, where
(1) one of the s-triazine moieties E in each tetraamine is replaced by the group E.sub.1 which forms a bridge between the two tetraamines T and T.sub.1,
E.sub.1 is ##STR4## or (2) the group E.sub.1 can have both termini in the same tetraamine T as in formula IIA where two of the E moieties of the tetraamine are replaced by one E.sub.1 group, or
(3) all three s-triazine substituents of tetraamine T can be E.sub.1 such that one E.sub.1 links T and T.sub.1 and a second E.sub.1 has both termini in tetraamine T,
L is cyclohexanediyl or octanediyl;
where in the compound of formula III
G, G.sub.1 and G.sub.2 are each tetraamines substituted by R.sub.1 -R.sub.4 as defined for formula I, except that G and G.sub.2 each have one of the s-triazine moieties E replaced by E.sub.1, and G.sub.1 has two of the triazine moieties E replaced by E.sub.1, so that there is a bridge between G and G.sub.1 and a second bridge between G.sub.1 and G.sub.2,
which mixture is prepared by reacting two to four equivalents of 2,4-bis(1-hydrocarbyloxy-2,2,6,6-piperidin-4-yl)butylamino!-6-chloro-s-tr iazine with one equivalent of N,N'-bis(3-amino-propyl)ethylenediamine.

17 more elements

A mixture of N,N',N"'-tris{2,4-bis(1-hydrocarbyloxy-2,2,6,6-tetramethylpiperidin-4-yl) alkylamino!-s-triazin-6-yl}-3,3'-ethylenediiminodipropylamine;

N,N',N"-tris-{2,4-bis(1-hydrocarbyloxy-2,2,6,6-tetramethylpiperidin-4-yl) alkylamino!-s-triazin-6-yl}-3,3'-ethylenediiminodipropylamine, and bridged derivatives as described by formulas I, II, IIA and III
R.sub.1 NH--CH.sub.2 CH.sub.2 CH.sub.2 NR.sub.2 CH.sub.2 CH.sub.2 NR.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 NHR.sub.4 (I)
T--E.sub.1 --T.sub.1 (II)
T--E.sub.1 (IIA)
G--E.sub.1 --G.sub.1 --E.sub.1 --G.sub.2 (III)
where in the tetraamine of formula I,
R.sub.1 and R.sub.2 are the s-triazine moiety E;
and one of R.sub.3 and R.sub.4 is the s-triazine moiety E with the other of R.sub.3 and R.sub.1 being hydrogen,
E is ##STR5## R is methyl, cyclohexyl or octyl, R.sub.5 is alkyl of 1 to 12 carbon atoms,
where in the compound of formula II or IIA when R is cyclohexyl or octyl,
T and T.sub.1 are each a tetraamine substituted by R.sub.1 -R.sub.4 as defined for formula I, where
(1) one of the s-triazine moieties E in each tetraamine is replaced by the group E.sub.1 which forms a bridge between the two tetraamines T and T.sub.1 .
E.sub.1 is ##STR6## or (2) the group E.sub.1 can have both termini in the same tetraamine T as in formula IIA where two of the E moieties of the tetraamine are replaced by one E.sub.1 group, or
(3) all three s-triazine substituents of tetraamine T can be E.sub.1 such that one E.sub.1 links T and T.sub.1 and a second E.sub.1 has both termini in tetraamine T,
L is cyclohexanediyl or octanediyl;
where in the compound of formula III
G, G.sub.1 and G.sub.2 are each tetraamines substituted by R.sub.1 -R.sub.4 as defined for formula I, except that G and G.sub.2 each have one of the s-triazine moieties E replaced by E.sub.1, and G.sub.1 has two of the triazine moieties E replaced by E.sub.1, so that there is a bridge between G and G.sub.1 and a second bridge between G.sub.1 and G.sub.2,
which mixture is prepared by reacting two to four equivalents of 2,4-bis(1-hydrocarbyloxy-2,2,6,6-piperidin-4-yl)butylamino!-6-chloro-s-tr iazine with one equivalent of N,N'-bis(3-amino-propyl)ethylenediamine.

15 more elements

Dependencies are inferred from the claim text.

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