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US 5,492,954 AGranted
Substituted 1,4-diamino-2-butene stabilizers and stabilized compositions
AssigneeCiba-Geigy Corporation
InventorsJoseph E. Babiarz, Glen T. Cunkle, Werner Rutsch
Life of this patent
Estimating the term…
Abstract
N,N,N',N'-Tetrasubstituted 1,4-diamino-2-butenes where the substituents are alkyl, cycloalkyl, aralkyl, aryl or mixtures thereof provide effective antioxidant protection to lubricants and/or synthetic polymers.
Claims17
A composition stabilized against the deleterious effects of heat or oxygen which comprises
- (a) a synthetic polymer, and
- (b) an effective stabilizing mount of a compound of formula I, II or III ##STR5## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently a linear or branched alkyl of 8 to 30 carbon atoms;
- alkyl of 1 to 20 carbon atoms substituted with cycloalkyl of 5 to 12 carbon atoms;
- or alkyl of 1 to 20 carbon atoms terminated with --OR.sub.5, --NR.sub.6 R.sub.7, --SR.sub.8, --COOR.sub.9 or --CONR.sub.10 R.sub.11, where R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 are independently alkyl of 1 to 20 carbon atoms or alkenyl of 3 to 18 carbon atoms, and R.sub.10 and R.sub.11 are independently hydrogen or the same meaning as R.sub.5 ;
- or alkyl of 3 to 18 carbon atoms interrupted by one or more --O--, --S--, --SO--, --SO.sub.2 --, --CO--, --COO--, --OCO--, --CONR.sub.12 --, --NR.sub.12 CO-- or --NR.sub.13 -- where R.sub.12 and R.sub.13 have the same meaning as R.sub.10 ;
- or R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently cycloalkyl of 5 to 12 carbon atoms;
- or alkenyl of 3 to 20 carbon atoms;
- E.sub.1 is aralkyl of 7 to 15 carbon atoms or said aralkyl substituted on the aryl ring by one to three groups selected from alkyl of 1 to 12 carbon atoms, --CN, --NO.sub.2, halogen, --OR.sub.5, --NR.sub.6 R.sub.7, --SR.sub.8, --COOR.sub.9 or --CONR.sub.10 R.sub.11, where R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 are as defined above,
- E.sub.2, E.sub.3 and E.sub.4 are independently a linear or branched alkyl of 1 to 30 carbon atoms;
- alkyl of 1 to 20 carbon atoms substituted with cycloalkyl of 5 to 12 carbon atoms;
- or alkyl of 1 to 20 carbon atoms terminated with --CN, --OR.sub.5, --NR.sub.6 R.sub.7, --SR.sub.8, --COOR.sub.9 or --CONR.sub.10 R.sub.11, where R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 are independently alkyl of 1 to 20 carbon atoms or alkenyl of 3 to 18 carbon atoms, and R.sub.10 and R.sub.11 are independently hydrogen or the same meaning as R.sub.5 ;
- or alkyl of 3 to 18 carbon atoms interrupted by one or more --O--, --S--, --SO--, --SO.sub.2 --, --CO--, --COO--, --OCO--, --CONR.sub.12 --, -- NR.sub.12 CO-- or --NR.sub.13 -- where R.sub.12 and R.sub.13 have the same meaning as R.sub.10 ;
- or E.sub.2, E.sub.3 and E.sub.4 are independently cycloalkyl of 5 to 12 carbon atoms, alkenyl of 3 to 20 carbon atoms, aralkyl of 7 to 15 carbon atoms or said aralkyl substituted on the aryl ring by one to three groups selected from alkyl of 1 to 12 carbon atoms, --CN;
- --NO.sub.2, halogen, --OR.sub.5, --NR.sub.6 R.sub.7, --SR.sub.8, --COOR.sub.9 or --CONR.sub.10 R.sub.11, where R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 are as defined above, or aryl of 6 to 10 carbon atoms or said aryl substituted by one to three substituents selected from the group consisting of alkyl of 1 to 20 carbon atoms, cycloalkyl of 5 to 12 carbon atoms and aralkyl of 7 to 15 carbon atoms, and
- T.sub.1, T.sub.2, T.sub.3 and T.sub.4 are independently phenyl or 1-naphthyl.
12 more elements
A composition stabilized against the deleterious effects of heat or oxygen which comprises
- (a) lubricant, and
- (b) an effective stabilizing amount of a compound of formula I, or II ##STR6## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently a linear or branched alkyl of 8 to 30 carbon atoms;
- alkyl of 1 to 20 carbon atoms substituted with cycloalkyl of 5 to 12 carbon atoms;
- or alkyl of 1 to 20 carbon atoms terminated with --OR.sub.5, --NR.sub.6 R.sub.7, --SR.sub.8, --COOR.sub.9 or --CONR.sub.10 R.sub.11, where R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 are independently alkyl of 1 to 20 carbon atoms or alkenyl of 3 to 18 carbon atoms, and R.sub.10 R.sub.11 are independently hydrogen or the same meaning as R.sub.5 ;
- or alkyl of 3 to 18 carbon atoms interrupted by one or more --O--, --S--, --SO--, --SO.sub.2 --, --CO--, --COO--, --OCO--, --CONR.sub.12 --, -- NR.sub.12 CO-- or --NR.sub.13 -- where R.sub.12 and R.sub.13 have the same meaning as R.sub.10 ;
- or R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently cycloalkyl of 5 to 12 carbon atoms;
- or alkenyl of 3 to 20 carbon atoms;
- E.sub.1 is aralkyl of 7 to 15 carbon atoms or said aralkyl substituted on the aryl ring by one to three groups selected from alkyl of 1 to 12 carbon atoms, --CN, --NO.sub.2, halogen, --OR.sub.5, --NR.sub.6 R.sub.7, --SR.sub.8, --COOR.sub.9 or --CONR.sub.10 R.sub.11, where R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 are as defined above, and
- E.sub.2, E.sub.3 E.sub.4 are independently a linear or branched alkyl of 1 to 30 carbon atoms;
- alkyl of 1 to 20 carbon atoms substituted with cycloalkyl of 5 to 12 carbon atoms;
- or alkyl of 1 to 20 carbon atoms terminated with --CN, --OR.sub.5, --NR.sub.6 R.sub.7, --SR.sub.8, --COOR.sub.9 or --CONR.sub.10 R.sub.11, where R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 are independently alkyl of 1 to 20 carbon atoms or alkenyl of 3 to 18 carbon atoms, and R.sub.10 R.sub.11 are independently hydrogen or the same meaning as R.sub.5 ;
- or alkyl of 3 to 18 carbon atoms interrupted by one or more --O--, --S--, --SO--, --SO.sub.2 --, --CO--, --COO--, --OCO--, --CONR.sub.12 --, --NR.sub.12 CO-- or --NR.sub.13 -- where R.sub.12 and R.sub.13 have the same meaning as R.sub.10 ;
- or E.sub.2, E.sub.3 and E.sub.4 are independently cycloalkyl of 5 to 12 carbon atoms, alkenyl of 3 to 20 carbon atoms, aralkyl of 7 to 15 carbon atoms or said aralkyl substituted on the aryl ring by one to three groups selected from alkyl of 1 to 12 carbon atoms, --CN, --NO.sub.2, halogen, --OR.sub.5, --NR.sub.6 R.sub.7, --SR.sub.8, --COOR.sub.9 or --CONR.sub.10 R.sub.11, where R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 are as defined above, or aryl of 6 to 10 carbon atoms or said aryl substituted by one to three substituents selected from the group consisting of alkyl of 1 to 20 carbon atoms, cycloalkyl of 5 to 12 carbon atoms and aralkyl of 7 to 15 carbon atoms.
10 more elements
Dependencies are inferred from the claim text.