Hindered piperidine carboxylic acids, metal salts thereof and stabilized compositions
AssigneeCiba-Geigy Corporation
InventorsChester E. Ramey, John J. Luzzi
Life of this patent
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Abstract
Compounds having the formula ##STR1## WHEREIN R.sub.1 and R.sub.2 are lower alkyl or cycloalkyl, R.sub.3 is hydrogen, alkyl, methoxyethyl, alkenyl, propargyl, benzyl or alkyl substituted benzyl, R.sub.4 is alkylene, alkyl-thio-alkyl or alkyl-oxo-alkyl, M is hydrogen or a metal, and z has a value of from 1 to 4, Are good light stabilizers. The carboxylic acids are prepared, for example, from 2,2,6,6-tetramethyl-piperidin-4-ol and sebacic acid to give o-mono(2,2,6,6-tetramethyl-piperidin-4-ol)sebacate. The metal salts of the acids are readily prepared by reacting the acids or their salts with a reactive form of the metal or metal complex.
Claims26
A composition of matter comprising a synthetic organic polymer normally subject to ultraviolet deterioration stabilized with 0.005 to 5% of a stabilizer having the formula ##STR8## wherein R.sub.1 and R.sub.2 independently of each other are straight- or branched-chain alkyl having from 1 to 6 carbon atoms, or together with the carbon to which they are bound form a cyclopentyl or cyclohexyl ring, which is unsubstituted or substituted with a methyl group,
- R.sub.3 is hydrogen, alkyl having 1 to 12 carbon atoms, .beta.-methoxyethyl, alkenyl having 3 to 4 carbon atoms, propargyl, benzyl, or alkyl substituted benzyl,
- R.sub.4 is straight- or branched-chain alkylene having 5 to 8 carbon atoms, or the group (CH.sub.2).sub.m Y(CH.sub.2).sub.n wherein Y is oxygen or sulfur and m and n independently of each other are an integer of from 1 to 3,
- M is hydrogen or a metal selected from the group consisting of barium, nickel, manganese, calcium, zinc, iron, sodium, cobalt, tin and dialkyl tin, and
- z has a value of from 1 to 4, the value of z being the same as the available valence of M
- said stabilizer bing incorporated into the synthetic organic polymer after polymerization.
The composition of claim 10 wherein R.sub.4 is the group (Ch.sub.2).sub.m Y(CH.sub.2).sub.n is Y, m and n are defined in claim 24.
A compound of the formula ##STR10## wherein R.sub.1 and R.sub.2 independently of each other are straight- or branched-chain alkyl having from 1 to 6 carbon atoms, or together with the carbon to which they are bound form a cyclopentyl or cyclohexyl ring, which is unsubstituted or substituted with a methyl group.
- R.sub.3 is hydrogen, alkyl having 1 to 12 carbon atoms, .beta.-methoxyethyl, alkenyl having 3 or 4 carbon atoms, propargyl, benzyl, or alkyl substituted benzyl,
- R.sub.4 is straight- or branched-chain alkylene having 5 to 8 carbon atoms, or the group (CH.sub.2).sub.m Y(CH.sub.2).sub.n wherein Y is oxygen or sulfur and m and n independently of each other are an integer of from 1 to 2,
- M is hydrogen or a metal selected from the group consisting of barium, calcium, and sodium, and the value of z is the same as the available valence of M.
A compound according to claim 21 wherein R.sub.4 wherein R.sub.4 is the group (CH.sub.2).sub.m Y(CH.sub.2).sub.n and Y, m and n are as defined in claim 35.
Dependencies are inferred from the claim text.