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US 5,204,422 AGranted
Peroxide free radical initiators containing hindered amine moieties with low basicity
AssigneeCiba-Geigy Corporation
InventorsRaymond Seltzer, Roland A. E. Winter, Peter J. Schirmann
Life of this patent
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Abstract
Compounds which contain peroxide linkages as well as a hindered amine light stabilizer moiety of low basicity function as free radical polymerization initiators and provide a polymer containing a hindered amine stabilizer chemically bonded to said polymer. The low basicity of the instant compounds prevents interaction with acid catalysts used in some polymerization systems.
Claims8
A process of preparing a homo- or copolymer containing a hindered amine light stabilizer moiety chemically bonded to the backbone of said polymer which process comprises
- polymerizing one or more ethylenically unsaturated monomers capable of being polymerized by free radicals in the presence of an effective initiating amount of a compound which is a free radical initiator which also contains a hindered amine light stabilizing moiety having low basicity, which compound has formula I ##STR4## a is 1 or 2, n and m are independently 0 and 1,
- R.sub.1 and R.sub.2 are independently alkyl of 1 to 4 carbon atoms, or R.sub.1 and R.sub.2 together are pentamethylene,
- R.sub.3 is hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, alkynyl of 2 to 8 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, alkoxy of 1 to 8 carbon atoms, alkoxycarbonyl of 2 to 7 carbon atoms, aryl of 6 to 10 carbon atoms, aralkyl of 7 to 15 carbon atoms, alkanoyl of 1 to 8 carbon atoms, aroyl of 7 to 16 carbon atoms, alkanoyloxy of 1 to 7 carbon atoms, or aroyloxy of 6 to 10 carbon atoms, or R.sub.3 together with R.sub.4 form a cyclic structure of 5 to 7 atoms,
- X is --O--, --S--, --NG--, --CO--, --SO--, --SO.sub.2 --, --OCO--, --OSO--, --OSO.sub.2 --, --NG--CO--, --NHCONH-- or --OCO--O-- where G is hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, alkynyl of 2 to 8 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, aryl of 6 to 10 carbon atoms, alkanoyl of 1 to 8 carbon atoms or G and R.sub.4 together form a cyclic structure of 5 to 7 carbon atoms,
- R.sub.4 is a diradical which is alkylene of 1 to 20 carbon atoms, arylene of 6 to 10 carbon atoms, cycloalkylene of 3 to 10 carbon atoms, aralkylene of 7 to 20 carbon atoms, alkynylene of 2 to 10 carbon atoms, alkadiynylene of 4 to 10 carbon atoms, alkenylene of 3 to 11 carbon atoms, alkadienylene of 5 to 11 carbon atoms, or said diradical interrupted by one or more oxygen, sulfur or nitrogen atoms,
- Y is --CO--, --SO.sub.2 --, --CR.sub.5 R.sub.6 --, --OCOE--, --NG--CO--E-- or --OCO--CO, where R.sub.5 and R.sub.6 are independently alkyl of 1 to 10 carbon atoms, aryl of 6 to 10 carbon atoms, alkynyl of 2 to 10 carbon atoms, alkenyl of 2 to 8 carbon atoms or cycloalkyl of 5 to 6 carbon atoms, or R.sub.5 and R.sub.6 together are alkylene of 4 to 9 carbon atoms, and when E is tert-alkyl, tert-cycloalkyl or tert-aralkyl, R.sub.6 is also --O--O--E,
- E, when a is 1, is hydrogen, alkanoyl of 2 to 20 carbon atoms, aroyl of 7 to 20 carbon atoms, tert-alkyl of 4 to 12 carbon atoms, tert-cycloalkyl of 4 to 12 carbon atoms, tert-aralkyl of 9 to 15 carbon atoms, alkoxycarbonyl of 2 to 20 carbon atoms, carbamoyl, phenylcarbamoyl, alkylcarbamoyl of 2 to 13 carbon atoms, cycloalkylcarbamoyl of 4 to 13 carbon atoms, alpha-hydroxyalkyl of 2 to 10 carbon atoms, alpha-hydroxycycloalkyl of 3 to 10 carbon atoms, alkylsulfonyl of 4 to 20 carbon atoms, cycloalkylsulfonyl of 3 to 12 carbon atoms, tert-alkoxyalkyl of 4 to 20 carbon atoms, tert-alkoxycycloalkyl of 4 to 20 carbon atoms, monovalent organometal, or the radical of formula II ##STR5## E, when a is 2, is di-tert-alkylene of 7 to 15 carbon atoms, di-tert-alkenylene of 8 to 16 carbon atoms, di-tert-alkynylene of 8 to 16 carbon atoms, di-tert-aralkylene of 12 to 20 carbon atoms, alkanedioyl of 3 to 12 carbon atoms, aryldicarbonyl of 8 to 16 carbon atoms or aralkyldicarbonyl of 9 to 18 carbon atoms, and
- T is formyl, --O--T.sub.1 or --OCO--T.sub.2, where
- T.sub.1 is alkyl of 1 to 36 carbon atoms, alkenyl of 2 to 18 carbon atoms, alkynyl of 2 to 18 carbon atoms, aralkyl of 7 to 15 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, cycloalkenyl of 5 to 12 carbon atoms, a radical of a saturated or unsaturated bicyclic or tricyclic hydrocarbon of 7 to 12 carbon atoms, or aryl of 6 to 10 carbon atoms or said aryl substituted by alkyl, and
- T.sub.2 is alkyl of 1 to 18 carbon atoms, alkoxy of 1 to 18 carbon atoms, phenyl or said phenyl substituted by hydroxy, alkyl or alkoxy;
- or amino or said amino mono- or disubstituted by alkyl or phenyl.
8 more elements
Dependencies are inferred from the claim text.