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US 5,597,854 AGranted
Latent light stabilizers
AssigneeCiba-Geigy Corporation
InventorsJean-Luc Birbaum, Gerhard Rytz, Vien Van Toan, Andreas Valet, Norbert W urms
Life of this patent
Estimating the term…
Abstract
The invention relates to compounds of the formula I ##STR1## in which n is 1 or 2, A is CH or a nitrogen atom, and the other radicals R.sup.1 to R.sup.25 are as defined in claim 1. The compounds of the formula I can advantageously be employed for stabilizing organic material against the harmful effect of light, oxygen and/or heat.
Claims16
A composition comprising
- A) an organic material which is sensitive to damage by light, oxygen and/or heat and
- B) a sufficient stabilizing amount of a compound of the formula I ##STR91## in which n is 1 or 2;
- A is CH or a nitrogen atom;
- R.sup.1 and R.sup.2, independently of one another, are H, C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl, trifluoromethyl or OR.sup.7 ;
- R.sup.3 and R.sup.4, independently of one another, are H, C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl, OR.sup.17, phenyl, CN, halogen or OR.sup.7 ;
- R.sup.5, in the case where n=1, is as a monovalent radical C.sub.6 -C.sub.18 alkyl, C.sub.1 -C.sub.18 alkoxy, halogen, --O--CO--R.sup.12, --O--SO.sub.2 --R.sup.13, ##STR92## or R.sup.5, in the case where n=1, is as defined for R.sup.17 or is --O--R.sup.17, and R.sup.5 as a monovalent radical in the case where neither of the radicals R.sup.1 and R.sup.2 is OR.sup.7 also comprises H or C.sub.1 -C.sub.5 alkyl;
- R.sup.5, in the case where n=2, is as a divalent radical --O--G--O--, where G is C.sub.2 -C.sub.16 alkylene, C.sub.4 -C.sub.12 alkenylene, xylylene or C.sub.3 -C.sub.20 alkylene which is interrupted by --O-- and/or is substituted by OR.sup.7, or G is one of the groups --CH.sub.2 CH(OR.sup.7)CH.sub.2 O--R.sup.20 --OCH.sub.2 CH(OR.sup.7)CH.sub.2 --, --CO--R.sup.21 --CO--, --CO--NH--R.sup.22 --NH--CO-- and --(CH.sub.2).sub.m --COO--R.sup.23 --OOC--(CH.sub.2).sub.m --, in which m is an integer in the range from 1 to 3, or is ##STR93## R.sup.6 is H, C.sub.2 -C.sub.18 alkenyl, --X--Z.sup.3, benzoyl which is unsubstituted or substituted on the phenyl ring by methyl, halogen, --CN or methoxy;
- or R.sup.6 is halogen, --SR.sup.14, SOR.sup.13, --SO.sub.2 R.sup.13, --C(Z.sup.3).dbd.N--Z.sup.3, --CH(Z.sup.3)--NH--Z.sup.3, a radical of the formula ##STR94## or a radical of the formula ##STR95## R.sup.7 is --CO--R.sup.11, --SO.sub.2 --R.sup.13, ##STR96## allyl or a group of the formula ##STR97## in which E is C.sub.3 -C.sub.18 alkylene or C.sub.4 -C.sub.18 alkenylene;
- R.sup.8 is C.sub.1 -C.sub.18 alkyl;
- C.sub.3 -C.sub.18 alkenyl;
- C.sub.3 -C.sub.20 alkyl which is interrupted by O, N or S and/or is substituted by OR.sup.7 ;
- C.sub.1 -C.sub.4 alkyl which is substituted by --P(O)(OR.sup.14).sub.2, --N(R.sup.9)(R.sup.10), --OCOR.sup.11 and/or OR.sup.7 ;
- glycidyl;
- C.sub.5 -C.sub.12 cycloalkyl or C.sub.7 -C.sub.11 phenylalkyl;
- or a group of the formula ##STR98## R.sup.9 and R.sup.10, independently of one another, are C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.12 alkoxyalkyl, C.sub.4 -C.sub.16 dialkylaminoalkyl or C.sub.5 -C.sub.12 cycloalkyl, or R.sup.9 and R.sup.10 together are C.sub.3 -C.sub.9 alkylene or -oxaalkylene or -azaalkylene;
- R.sup.11 is C.sub.1 -C.sub.18 alkyl, halogen-substituted C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.12 cycloalkyl, C.sub.2 -C.sub.18 alkenyl, --CH.sub.2 --CO--CH.sub.3, C.sub.7 -C.sub.12 aralkyl, C.sub.1 -C.sub.12 alkoxy;
- or phenyl which is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen and/or benzyl;
- R.sup.12 is C.sub.1 -C.sub.18 alkyl, halogen-substituted C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.12 cycloalkyl, C.sub.2 -C.sub.18 alkenyl, phenyl or --R.sup.15 --O--CO--R.sup.11, or is a group of the formula ##STR99## R.sup.13 is C.sub.1 -C.sub.12 alkyl, C.sub.6 -C.sub.10 aryl, or C.sub.7 -C.sub.18 alkylaryl;
- R.sup.14 is C.sub.1 -C.sub.12 alkyl, phenyl or C.sub.7 -C.sub.15 phenylalkyl;
- R.sup.15 is C.sub.1 -C.sub.18 alkylene or C.sub.2 -C.sub.18 alkenylene;
- R.sup.16 is hydrogen, N-oxide, formyl, C.sub.2 -C.sub.8 alkanoyl, C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.18 alkoxy, C.sub.5 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.12 cycloalkoxy, C.sub.7 -C.sub.11 phenylalkyl, C.sub.7 -C.sub.11 phenylalkyl which is substituted on the phenyl ring by 1 to 3 C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.8 alkanoyl radicals, or is C.sub.7 -C.sub.11 phenylalkoxy;
- R.sup.17 is C.sub.5 -C.sub.18 alkyloxycarbonyl, C.sub.2 -C.sub.18 alkenyl or C.sub.1 -C.sub.18 alkyl which is substituted by OR.sup.7, C.sub.1 -C.sub.18 alkoxy, C.sub.5 -C.sub.12 cycloalkoxy, C.sub.2 -C.sub.18 alkanoyl, C.sub.2 -C.sub.8 alkenyloxy, halogen, --COOR.sup.8, --CONH.sub.2, --CONHR.sup.9, --CON(R.sup.9)(R.sup.10), --NHR.sup.9, --N(R.sup.9)(R.sup.10), --NHCOR.sup.11, --CN, --OCOR.sup.11, a group of the formula ##STR100## and/or phenoxy which is unsubstituted or substituted by C.sub.1 -C.sub.18 alkyl, C.sub.1 -C.sub.18 alkoxy or halogen, or R.sup.17 is C.sub.3 -C.sub.50 oalkyl which is interrupted by O or may be substituted by OR.sup.7, or is glycidyl, C.sub.5 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.12 cycloalkyl which is substituted by OR.sup.7, C.sub.1 -C.sub.4 alkyl or --OCOR.sup.11, or is C.sub.7 -C.sub.11 phenylalkyl which is unsubstituted or substituted by OR.sup.7, Cl or CH.sub.3 ;
- R.sup.18 and R.sup.19, independently of one another, are C.sub.1 -C.sub.12 alkoxy, phenoxy, C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl, benzyl, tolyl or phenyl;
- R.sup.20 is C.sub.2 -C.sub.10 alkylene, C.sub.4 -C.sub.50 alkylene which is interrupted by --O--, or R.sup.20 is phenylene or a -phenylene-D-phenylene- group in which D is --O--, --S--, --SO.sub.2 --, --CH.sub.2 -- or --C(CH.sub.3).sub.2 --;
- R.sup.21 is C.sub.2 -C.sub.10 alkylene, C.sub.6 -C.sub.12 arylene, C.sub.2 -C.sub.6 alkenylene, or C.sub.2 -C.sub.10 alkylene which is interrupted by O or S;
- R.sup.22 is C.sub.2 -C.sub.10 alkylene, phenylene, tolylene, diphenylenemethane or ##STR101## R.sup.23 is C.sub.2 -C.sub.10 alkylene or C.sub.4 -C.sub.20 alkylene which is interrupted by --O--;
- R.sup.24 and R.sup.25, independently of one another, are H, C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.1 -C.sub.12 alkoxy, C.sub.3 -C.sub.18 alkenyloxy, halogen, trifluoromethyl, C.sub.7 -C.sub.11 phenylalkyl, phenyl, phenyl which is substituted by C.sub.1 -C.sub.18 alkyl, C.sub.1 -C.sub.18 alkoxy or halogen, or are phenoxy, or phenoxy which is substituted by C.sub.1 -C.sub.18 alkyl, C.sub.1 -C.sub.18 alkoxy or halogen;
- X is a direct bond or --CO--;
- Z.sup.1 and Z.sup.2, independently of one another, are C.sub.1 -C.sub.12 alkyl or together are C.sub.4 -C.sub.10 alkylene, which may be interrupted by an oxygen atom;
- Z.sup.3 is C.sub.1 -C.sub.20 alkyl or C.sub.7 -C.sub.15 phenylalkyl;
- Z.sup.4 and Z.sup.8, independently of one another, are hydrogen or methyl;
- and
- Z.sup.5, Z.sup.6 and Z.sup.7, independently of one another, are C.sub.1 -C.sub.18 alkyl, cyclohexyl, phenyl or C.sub.1 -C.sub.18 alkoxy.
30 more elements
A compound of the formula Ia ##STR112## in which n is 1 or 2;
- A is CH or a nitrogen atom;
- R.sup.1 and R.sup.2, independently of one another, are H, C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl, trifluoromethyl or OR.sup.7 ;
- R.sup.3 and R.sup.4, independently of one another, are H, C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl, OR.sup.17, halogen or OR.sup.7 ;
- R.sup.5, in the case where n=1, is as a monovalent radical C.sub.6 -C.sub.18 alkyl, C.sub.1 -C.sub.18 alkoxy, halogen, --O--SO.sub.2 --R.sup.13, ##STR113## or R.sup.5, in the case where n=1, is as defined for R.sup.17 or is --O--R.sup.17, and R.sup.5 as a monovalent radical in the case where neither of the radicals R.sup.1 and R.sup.2 is OR.sup.7 also comprises H, C.sub.1 -C.sub.5 alkyl;
- R.sup.5, in the case where n=2, is as a divalent radical --O--G--O--, where G is C.sub.2 -C.sub.16 alkylene, C.sub.4 -C.sub.12 alkenylene, xylylene or C.sub.3 -C.sub.20 alkylene which is interrupted by --O-- and/or is substituted by OR.sup.7, or G is one of the groups --CH.sub.2 CH(OR.sup.7)CH.sub.2 O--R.sup.20 --OCH.sub.2 CH(OR.sup.7)CH.sub.2 --, --CO--R.sup.21 --CO--, --CO--NH--R.sup.22 --NH--CO-- and --(CH.sub.2).sub.m --COO--R.sup.23 --OOC--(CH.sub.2).sub.m --, in which m is an integer in the range from 1 to 3, or is ##STR114## R.sup.6 is H, C.sub.2 -C.sub.18 alkenyl, --X--Z.sup.3, benzoyl which is unsubstituted or substituted on the phenyl ring by methyl, halogen, --CN or methoxy, or R.sup.6 is halogen, --SR.sup.14, --SOR.sup.13, --SO.sub.2 R.sup.13, --C(Z.sup.3).dbd.N--Z.sup.3, --CH(Z.sup.3)--NH--Z.sup.3, a radical of the formula ##STR115## or a radical of the formula ##STR116## R.sup.7 is --CO--R.sup.11, --SO.sub.2 --R.sup.13, ##STR117## allyl or a group of the formula ##STR118## in which E is C.sub.3 -C.sub.18 alkylene or C.sub.4 -C.sub.18 alkenylene;
- R.sup.8 is C.sub.1 -C.sub.18 alkyl, C.sub.3 -C.sub.18 alkenyl, C.sub.3 -C.sub.20 alkyl which is interrupted by O, N or S and/or is substituted by OR.sup.7, or R.sup.8 is C.sub.1 -C.sub.4 alkyl which is substituted by --P(O)(OR.sup.14).sub.2, --N(R.sup.9)(R.sup.10), --OCOR.sup.11 and/or OR.sup.7, or R.sup.8 is glycidyl, C.sub.5 -C.sub.12 cycloalkyl or C.sub.7 -C.sub.11 phenylalkyl, or a group of the formula ##STR119## R.sup.9 and R.sup.10, independently of one another, are C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.12 alkoxyalkyl, C.sub.4 -C.sub.16 dialkylaminoalkyl or C.sub.5 -C.sub.12 cycloalkyl, or R.sup.9 and R.sup.10 together are C.sub.3 -C.sub.9 alkylene or -oxaalkylene or -azaalkylene;
- R.sup.11 is C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.12 cycloalkyl, halogen-substituted C.sub.1 -C.sub.18 alkyl, C.sub.2 -C.sub.18 alkenyl, --CH.sub.2 --CO--CH.sub.3, C.sub.7 -C.sub.12 aralkyl, C.sub.1 C.sub.12 alkoxy, or phenyl which is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen and/or benzyl;
- R.sup.13 is C.sub.1 -C.sub.12 alkyl, C.sub.6 -C.sub.10 aryl or C.sub.7 -C.sub.18 alkylaryl;
- R.sup.14 is C.sub.1 -C.sub.12 alkyl, phenyl or C.sub.7 -C.sub.15 phenylalkyl;
- R.sup.15 is C.sub.1 -C.sub.18 alkylene or C.sub.2 -C.sub.18 alkenylene;
- R.sup.16 is hydrogen, N-oxide, formyl, C.sub.2 -C.sub.8 alkanoyl, C.sub.1 -C.sub.18 alkyl, C.sub.1 -C.sub.18 alkoxy,
- C.sub.5 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.12 cycloalkoxy, C.sub.7 -C.sub.11 phenylalkyl, C.sub.7 -C.sub.11 phenylalkyl which is substituted on the phenyl ring by 1 to 3 C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.8 alkanoyl radicals, or is C.sub.7 -C.sub.11 phenylalkoxy;
- R.sup.17 is C.sub.5 -C.sub.18 alkyloxycarbonyl, C.sub.2 -C.sub.18 alkenyl or C.sub.1 -C.sub.18 alkyl which is substituted by OR.sup.7, C.sub.1 -C.sub.18 alkoxy, C.sub.5 -C.sub.12 cycloalkoxy, C.sub.2 -C.sub.18 alkanoyl, C.sub.2 -C.sub.8 alkenyloxy halogen, --COOR.sup.8, --CONH.sub.2, --CONHR.sup.9, --CON(R.sup.9)(R.sup.10), --NHR.sup.9, --N(R.sup.9)(R.sup.10), --NHCOR.sup.11, --CN, --OCOR.sup.11, a group of the formula ##STR120## and/or phenoxy which is unsubstituted or substituted by C.sub.1 -C.sub.18 alkyl, C.sub.1 -C.sub.18 alkoxy or halogen, or R.sup.17 is C.sub.3 -C.sub.50 alkyl which is interrupted by O and may be substituted by OR.sup.7, or is glycidyl, C.sub.5 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.12 cycloalkyl which is substituted by OR.sup.7, C.sub.1 -C.sub.4 alkyl or --OCOR.sup.11, or is C.sub.7 -C.sub.11 phenylalkyl which is unsubstituted or substituted by OR.sup.7, Cl or CH.sub.3 ;
- R.sup.18 and R.sup.19, independently of one another, are C.sub.1 -C.sub.12 alkoxy, phenoxy, C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.2 cycloalkyl, benzyl, tolyl or phenyl;
- R.sup.20 is C.sub.2 -C.sub.10 alkylene, C.sub.4 -C.sub.50 alkylene which is interrupted by --O--, phenylene or a -phenylene-D-phenylene- group in which D is --O--, --S--, --SO.sub.2 --, --CH.sub.2 -- or --C(CH.sub.3).sub.2 --;
- R.sup.21 is C.sub.2 -C.sub.10 alkylene, C.sub.2 -C.sub.10 alkylene which is interrupted by O or S, or is C.sub.6 -C.sub.12 arylene or C.sub.2 -C.sub.6 alkenylene;
- R.sup.22 is C.sub.2 -C.sub.10 alkylene, phenylene, tolylene, diphenylenemethane or ##STR121## R.sup.23 is C.sub.2 -C.sub.10 alkylene or C.sub.4 -C.sub.20 alkylene which is interrupted by --O--;
- R.sup.24 and R.sup.25, independently of one another, are H, C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.1 -C.sub.12 alkoxy, C.sub.3 -C.sub.18 alkenyloxy, halogen, trifluoromethyl, C.sub.7 -C.sub.11 phenylalkyl, phenyl, phenyl which is substituted by C.sub.1 -C.sub.18 alkyl, C.sub.1 -C.sub.18 alkoxy or halogen, or are phenoxy, or phenoxy which is substituted by C.sub.1 -C.sub.18 alkyl, C.sub.1 -C.sub.18 alkoxy or halogen;
- X is a direct bond or --CO--;
- Z.sup.1 and Z.sup.2, independently of one another, are C.sub.1 -C.sub.12 alkyl or together are C.sub.4 -C.sub.10 alkylene, which may be interrupted by an oxygen atom;
- Z.sup.3 is C.sub.1 -C.sub.20 alkyl or C.sub.7 -C.sub.15 phenylalkyl;
- Z.sup.4 and Z.sup.8, independently of one another, are hydrogen or methyl;
- and
- Z.sup.5, Z.sup.6 and Z.sup.7, independently of one another, are C.sub.1 -C.sub.8 alkyl, cyclohexyl, phenyl or C.sub.1 -C.sub.18 alkoxy.
21 more elements
Dependencies are inferred from the claim text.