1-Aza-4-thiacyclohexane-4,4-dioxide derivatives and their use as agents protecting against light rays
AssigneeCiba-Geigy Corporation
InventorJean Rody
Life of this patent
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Abstract
New 1-aza-4-thiacyclohexane-4,4-dioxide derivatives are used alone or in combination with other stabilizers for stabilizing organic materials. The new compounds are prepare by reacting substituted diallylsulfides with ammonia, amines or hydrazines.
Claims29
A composition containing organic polymer and a compound of the formula I ##EQU11## wherein R.sub.1 ,R.sub.2 ,R.sub.3 and R.sub.4 each independently are lower alkyl, or R.sub.1 and R.sub.2 and/or R.sub.3 and R.sub.4 together with the carbon atom to which they are bound form a cycloalkyl ring, and
- X is hydrogen, unsubstituted alkyl, substituted alkyl selected from hydroxyalkyl, carboxyalkyl, alkyl substituted with ester groups selected from alkoxycarbonylalkyl, alkylcarbonyloxyalkyl, arylcarbonyloxyalkyl, cycloalkylcarbonyloxyalkyl, and aralkylcarbonyloxyalkyl, amidoalkyl, nitriloalkyl, alkyl substituted with ether groups, alkyl substituted with thioether groups, alkyl substituted with arylthio groups, alkyl substituted with sulphoxide groups, alkyl substituted with sulphone groups, aminoalkyl unsubstiuted on the nitrogen atom, aminoalkyl substituted on the nitrogen atom with alkyl or nitriloalkyl, and haloalkyl, alkenyl, alkynyl, unsubstituted aralkyl, aralkyl substituted on the alkylene moiety by hydroxy, alkylcarbonyloxy, arylcarbonyloxy or halogen, acyl, halogen, --O.,--.NO, or NR.sub.5 R.sub.6, wherein R.sub.5 and R.sub.6 each independently are hydrogen, unsubstituted alkyl, substituted alkyl selected from hydroxyalkyl, carboxyalkyl, alkyl substituted with ester groups selected from alkoxycarbonyalkyl, alkylcarbonyloxyalkyl, arylcarbonyloxyalkyl, cycloalkylcarbonyloxyalkyl, or aralkylcarbonyloxyalkyl, amidoalkyl, nitriloalkyl, alkyl substituted with ether groups, alkyl substituted with thioether groups, alkyl substituted with arylthio groups, alkyl substituted with sulphoxide groups, alkyl substituted with sulphone groups, aminoalkyl unsubstituted on the nitrogen atom, aminoalkyl substituted on the nitrogen atom with alkyl, or nitriloalkyl, and haloalkyl;
- or R.sub.5 is acyl, or R.sub.5 and R.sub.6 together with the nitrogen atom to which they are bound form a ring,
- or their stabilizer compatible salts with organic or inorganic acids.
A composition according to claim 1 containing a compound of formula I wherein
- R.sub.1, r.sub.2, r.sub.3 and R.sub.4 are alkyl having 1 to 4 carbon atoms, or R.sub.1 and R.sub.2 and R.sub.3 and R.sub.4 together with the carbon atoms to which they are bound form a cyclopentane or cyclohexane ring, and
- X is hydrogen, unsubstituted alkyl having 1 to 18 carbon atoms, substituted alkyl as defined in claim 69, alkenyl having 3 to 18 carbon atoms, alkynyl having 3 to 14 carbon atoms, unsubstituted aralkyl having 7 to 11 carbon atoms, aralkyl having 9 to 18 carbon atoms which is substituted on the alkylene moiety by hydroxy, alkylcarbonyloxy, arylcarbonyloxy or halogen, acyl of the formulae R.sub.7 CO-- or R.sub.7 SO.sub.2 -- wherein R.sub.7 is alkyl having 1 to 18 carbon atoms, aryl having 6 to 10 carbon atoms or aralkyl having 7 to 11 carbon atoms,
- --O, --NO or --NR.sub.5 R.sub.6 wherein R.sub.5 and R.sub.6 each independently are hydrogen, unsubstituted alkyl having 1 to 12 carbon atoms, substituted alkyl as defined in claim 69, or R.sub.5 is R.sub.7 CO-- or R.sub.7 SO.sub.2 --, wherein R.sub.7 is as defined above, or R.sub.5 and R.sub.6 together with the nitrogen atom to which they are bound form a ring,
- or their stabilizer compatible salts with hydrohalic acids, sulphuric acid, carboxylic acids, sulphonic acids, or phosphorus-containing acids.
A composition according to claim 1 containing a compound of formula I wherein
- R.sub.1, r.sub.2, r.sub.3 and R.sub.4 are alkyl having 1 or 2 carbon atoms, or R.sub.1 and R.sub.2 and R.sub.3 and R.sub.4 together with the carbon atom to which they are bound form a cyclohexane ring;
- and
- X is hydrogen, unsubstituted alkyl having 1 to 12 carbon atoms, substituted alkyl as defined in claim 69, alkenyl having 3 to 8 carbon atoms, propargyl, aralkyl having 7 to 11 carbon atoms, aralkyl having 9 to 18 carbon atoms which is substituted on the alkylene moiety by hydroxy, carboxylic acid ester groups or halogen, acyl of the formulae R.sub.7 CO-- or R.sub.7 SO.sub.2 -- wherein R.sub.7 is alkyl having 1 to 12 carbon atoms, aryl having 6 to 10 carbon atoms or aralkyl having 7 to 11 carbon atoms, bromine, chlorine, --O.sup.. or --NR.sub.5 R.sub.6 wherein R.sub.5 and R.sub.6 each independently are hydrogen, alkyl having 1 to 4 carbon atoms, or R.sub.5 is R.sub.7 CO-- or R.sub.7 SO.sub.2 --, wherein R.sub.7 is as defined above, or their stabilizer compatible salts with hydrohalic acids, sulphuric acid, phosphoric acid, carboxylic acids having 1 to 18 carbon atoms, sulphonic acids having 1 to 12 carbon atoms or phosphorus-organic acids having 1 to 20 carbon atoms.
A stabilizer system consisting of a) at least one compound of formula I ##EQU18## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each independently are lower alkyl, or R.sub.1 and R.sub.2 and/or R.sub.3 and R.sub.4 together with the carbon atom to which they are bound form a cycloalkyl ring, and
- X is hydrogen, unsubstituted alkyl, substituted alkyl selected from hydroxyalkyl, carboxyalkyl, alkyl substituted with ester groups selected from alkoxycarbonylalkyl, alkylcarbonyloxyalkyl, arylcarbonyloxyalkyl, cycloalkylcarbonyloxyalkyl, and aralkylcarbonyloxyalkyl, amidoalkyl, nitriloalkyl, alkyl substituted with ether groups, alkyl substituted with thioether groups, alkyl substituted with arylthio groups, alkyl substituted with sulphoxide groups, alkyl substituted with sulphone groups, aminoalkyl unsubstituted on the nitrogen atoms, aminoalkyl substituted on the nitrogen atom with alkyl or nitriloalkyl, and haloalkyl, alkenyl, alkynyl, unsubstituted aralkyl, aralkyl substituted on the alkylene moiety by hydroxy, alkylcarbonyloxy, arylcarbonyloxy or halogen, acyl, halogen, --O.sup.., --NO, or NR.sub.5 R.sub.6, wherein R.sub.5 and R.sub.6 each independently are hydrogen, unsubstituted alkyl, substituted alkyl selected from hydroxyalkyl, carboxyalkyl, alkyl substituted with ester groups selected from alkoxycarbonyalkyl, alkylcarbonyloxyalkyl, arylcarbonyloxyalkyl, cycloalkylcarbonyloxyalkyl, or aralkylcarbonyloxyalkyl, amidoalkyl, nitriloalkyl, alkyl substituted with ether groups, alkyl substituted with thioether groups, alkyl substituted with arylthio groups, alkyl substituted with sulphoxide groups, alkyl substituted with sulphone groups, aminoalkyl unsubstituted on the nitrogen atom, aminoalkyl substituted on the nitrogen atom with alkyl or nitriloalkyl, haloalkyl;
- or R.sub.5 is acyl, or R.sub.5 and R.sub.6 together with the nitrogen atom to which they are bound form a ring, and (b) at least one co-stabilizer of the following formulae II, III, IV, V, VI, VII or VIII:
- ##SPC13##
- wherein the symbols have the following meanings:
- L.sub.1 hydrogen, alkyl, alkenyl or aralkyl,
- L.sub.2 hydrogen, alkyl or chlorine,
- L.sub.3 hydrogen, hydroxy, carboxy, alkoxy or alkyl,
- L.sub.4 hydrogen, hydroxy, alkoxy, alkenyloxy, aralkoxy or alkyl,
- L.sub.5 hydrogen, alkyl, alkenyl, cycloalkyl, aralkyl, aryl, acylamino, acylaminoalkyl or halogen,
- L.sub.6 hydrogen, alkyl, hydroxy, alkoxy or acylamino,
- L.sub.7 hydrogen, alkyl, alkenyl, cycloalkyl, aralkyl, aryl, alkoxy, halogen, carboxy, alkoxy-carbonyl, alkoxycarbonylalkyl or acylamino,
- L.sub.8 hydrogen, alkyl, hydroxy, alkoxy, halogen, acylamino, carboxy, alkoxy-carbonyl, acyloxy, carbamoyl, alkoxysulphonyl, aryloxysulphonyl or sulphonamido,
- L.sub.9 hydrogen, alkyl or halogen,
- L.sub.10 and L.sub.12 each independently represent hydrogen, alkyl, alkoxy, alkenyloxy, aralkoxy, aryloxy, halogen or alkoxycarbonyl,
- L.sub.11 and L.sub.13 each independently represent hydrogen or alkyl,
- L.sub.14 and L.sub.15 each independently represent hydrogen, alkyl, cycloalkyl or aralkyl,
- L.sub.16 hydrogen, alkoxy or aralkoxy,
- L.sub.17 alkyl or aryl,
- L.sub.18 alkyl, cycloalkyl or aralkyl,
- L.sub.19 alkyl or aralkyl,
- L.sub.20 hydrogen, alkyl, alkoxy or halogen,
- L.sub.21 cyano or alkoxycarbonyl, and
- L.sub.22 hydrogen or alkyl.
- wherein the weight ratio of the compounds of formula I to the compounds of formulae II-VIII is from 1:10 to 10:1.
Dependencies are inferred from the claim text.