Perfluoroalkyl substituted hydroxyphenylalkanoic ester antioxidants and stabilized compositions
AssigneeCiba-Geigy Corporation
InventorsRobert A. Falk, Eduard K. Kleiner
Life of this patent
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Abstract
Perfluoroalkyl substituted neopentyl alcohols can be reacted with substituted hydroxphenylalkanoic esters to form perfluoroalkyl containing hydroxyphenylalkanoic ester antioxidants. The perfluoroalkyl substituted hindered hydroxyphenyl alkanoates are stablizers which confer superior processing stability to polymers processed at elevated temperatures such as polypropylene, as well as protecting said polymers from thermal and oxidative degradation.
Claims28
A compound of formula I, II or III ##STR6## wherein R.sub.1 and R.sub.2 are independently alkyl of 1 to 12 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, said cycloalkyl substituted by alkyl of 1 to 4 carbon atoms, phenyl, phenylalkyl of 7 to 15 carbon atoms or said phenyl or said phenylalkyl substituted on the phenyl ring by alkyl of 1 to 4 carbon atoms, by --OH, by methoxy or by a mixture thereof,
- R.sub.3 is hydrogen or alkyl of 1 to 4 carbon atoms, or
- R.sub.2 and R.sub.3 together are tetramethylene,
- A is a direct bond or a straight or branched chain alkylene of 1 to 8 carbon atoms,
- R.sub.f is independently a straight or branched chain perfluoroalkyl of 1 to 14 carbon atoms, perfluoroalkyl of 2 to 6 carbon atoms substituted by perfluoroalkoxy of 2 to 6 carbon atoms, or an oligo(hexafluoropropene oxide) terminal group,
- n is 1 or 0,
- when n is 1, E is independently a branched or straight chain alkylene of 1 to 10 carbon atoms or said alkylene interrupted by one to three groups selected from the group consisting of --NR--, --O--, --S--, --SO.sub.2 --, --COO--, --OOC--, --CONR--, --NRCO--, --SO.sub.2 NR--, --NRSO.sub.2 --, or terminated at the R.sub.f end with --CONR-- or --SO.sub.2 NR--, where R.sub.f is attached to the carbon or sulfur atom, an X is --S--, --O--, --SO.sub.2 --, --NR--, or --COO--, or
- when n is 0, X is a direct bond, --CONR-- or --SO.sub.2 NR--, where R.sub.f is attached to the carbon or sulfur atom, and where R is independently hydrogen, alkyl of 1 to 6 carbon atoms or hydroxyalkyl of 2 to 6 carbon atoms, and
- m is 1, 2 or 3.
A stabilized composition which comprises
- (a) an organic material subject to thermal and oxidative degradation which is selected from the group consisting of a polymer, a wax, an oil, a fat and a lubricant, and
- (b) an effective stabilizing amount of a compound of formula I, II or III ##STR7## wherein R.sub.1 and R.sub.2 are independently alkyl of 1 to 12 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, said cycloalkyl substituted by alkyl of 1 to 4 carbon atoms, phenyl, phenylalkyl of 7 to 15 carbon atoms or said phenyl or said phenylalkyl substituted on the ring by alkyl of 1 to 4 carbon atoms, by --OH, by methoxy or by a mixture thereof,
- R.sub.3 is hydrogen or alkyl of 1 to 4 carbon atoms, or
- R.sub.2 R.sub.3 together are tetramethylene,
- A is a direct bond or a straight or branched chain alkylene of 1 to 8 carbon atoms,
- R.sub.f is independently a straight or branched chain perfluoroalkyl of 1 to 14 carbon atoms, perfluoroalkyl of 2 to 6 carbon atoms substituted by perfluoroalkoxy of 2 to 6 carbon atoms, or an oligo(hexafluoropropene oxide) terminal group,
- n is 1 or 0,
- when n is 1, E is independently a branched or straight chain alkylene of 1 to 10 carbon atoms or said alkylene interrupted by one to three groups selected from the group consisting of --NR--, --O--, --S--, --SO.sub.2 --, --COO--, --OOC--, --CONR--, --NRCO--, --SO.sub.2 NR--, --NRSO.sub.2 --, or terminated at the R.sub.f end with --CONR-- or --SO.sub.2 NR--, where R.sub.f is attached to the carbon or sulfur atom, and X is --S--, --O--, --SO.sub.2 --, --NR--, or --COO--, or
- when n is 0, X is a direct bond, --CONR-- or --SO.sub.2 NR--, where R.sub.f is attached to the carbon or sulfur atom, and where R is independently hydrogen, alkyl of 1 to 6 carbon atoms or hydroxyalkyl of 2 to 6 carbon atoms, and
- m is 1, 2 or 3.
Dependencies are inferred from the claim text.