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US 5,672,704 AGranted
2-Hydroxyphenyl-s-Triazines substituted with ethylenically unsaturated moieties
AssigneeCiba-Geigy Corporation
InventorsVien Van Toan, David George Leppard, Gerhard Rytz, Norbert Wurms, Pascal Hayoz
Life of this patent
Estimating the term…
Abstract
s-Triazine UV absorbers of formula I ##STR1## where R.sub.1 is ##STR2## --CH.sub.2 --C(.dbd.CH.sub.2)--R.sub.10, --(CH.sub.2).sub.p --SiR.sub.11 R.sub.11 '--CH.dbd.CH.sub.2, --C(.dbd.O)--(CH.sub.2).sub.q --CH.dbd.CH.sub.2 or --C(.dbd.O)--O--CH.sub.2 --C(.dbd.CH.sub.2)--R.sub.10 ; and E.sub.1 and E.sub.2 are phenyl groups which may be unsubstituted or substituted with a variety of substituents including inter alia alkyl, OH and R.sub.1 ; are polymerizable and are effective stabilizers for a variety of polymeric and other organic substrates.
Claims4
A compound of the formula I ##STR66## in which E.sub.1 and E.sub.2, independently of one another, are each a group of the formula Ia or Ib ##STR67## in which R.sub.1 is ##STR68## --(CH.sub.2).sub.p --SiR.sub.11 R.sub.11 '--CH.dbd.CH.sub.2, --C(.dbd.O)--(CH.sub.2).sub.q --CH.dbd.CH.sub.2 or --C(.dbd.O)--O--;
- and
- in the case where R.sub.3 ' is --O--CR.sub.8 R.sub.8 '--(CH.sub.2).sub.l --XA, R.sub.1 can additionally be C.sub.1 -C.sub.18 alkyl or C.sub.3 -C.sub.20 alkyl interrupted by --O--, --CO--O-- or --O--CO--;
- and,
- in the case where E.sub.1 is a group of the formula Ia in which neither of the radicals R.sub.2 and R.sub.14 is hydrogen, R.sub.1 can additionally be --A, --CH.sub.2 --CH(XA)--CH.sub.2 --O--R.sub.7, A is --C(.dbd.O)--CR.sub.5 .dbd.CH--R.sub.6 ;
- --CR.sub.8 R'.sub.8 --(CH.sub.2).sub.l --XA, --CH.sub.2 --CH(OA)--R.sub.9, --CH.sub.2 CH(OH)--CH.sub.2 --XA, --CHR.sub.8 --(CH.sub.2).sub.r --C(.dbd.O)--O--CH.sub.2 --CH(OH)--CH.sub.2 --OA and --CR.sub.8 R'.sub.8 --(CH.sub.2).sub.l --C(.dbd.O)--XA;
- and,
- in the case where E.sub.1 is a group of the formula Ib, R.sub.1 can additionally be --CH.sub.2 --CH(XA)--CH.sub.2 --O--R.sub.7 ;
- R.sub.2, independently of one another, are H, C.sub.1 -C.sub.12 alkyl, cyclohexyl, C.sub.3 -C.sub.6 alkenyl, halogen, phenyl or trifluoromethyl;
- R.sub.2 ', independently of one another, are C.sub.1 -C.sub.18 alkoxy, C.sub.3 -C.sub.18 alkenoxy, --OH or --O--CO--R.sub.12 ;
- R.sub.3 and R.sub.3 ', independently of one another, are H, --OH, --O--CH.sub.2 --CH(XA)--CH.sub.2 --O--R.sub.7, ##STR69## --O--CH.sub.2 --C(.dbd.CH.sub.2)--R.sub.10, --O--(CH.sub.2).sub.p --SiR.sub.11 R.sub.11 '--CH.dbd.CH.sub.2, --O--C(.dbd.O)--(CH.sub.2).sub.q --CH.dbd.CH.sub.2, --O--C(.dbd.O)--O--CH.sub.2 --C(.dbd.CH.sub.2)--R.sub.10, --O--CR.sub.8 R.sub.8 '--(CH.sub.2).sub.l --XA, --O--CH.sub.2 CH(OA)--R.sub.9, --O--CH.sub.2 --CH(OH)--CH.sub.2 --XA, --O--CHR.sub.8 --(CH.sub.2).sub.r --C(.dbd.O)--O--CH.sub.2 --CH(OH)--CH.sub.2 --OA, --CR.sub.8 R'.sub.8 --(CH.sub.2).sub.l --C(.dbd.O)--XA, C.sub.1 -C.sub.18 alkyl, C.sub.6 -C.sub.12 cycloalkyl, C.sub.3 -C.sub.18 alkenyl, --OR.sub.131, halogen, trifluoromethyl, phenyl, phenyl-C.sub.1 -C.sub.4 alkyl, --CN, C.sub.1 -C.sub.18 alkyl-S(.dbd.O).sub.t -- or phenyl-S(.dbd.O).sub.t --;
- R.sub.4, R.sub.4 ' and R.sub.4 ", independently of one another, are H, C.sub.1 -C.sub.18 alkyl, C.sub.3 -C.sub.6 alkenyl, --OR.sub.131, halogen, trifluoromethyl, phenyl, phenyl-C.sub.1 -C.sub.4 alkyl, mono- to tri-C.sub.1 -C.sub.4 alkyl-substituted phenyl-C.sub.1 -C.sub.4 alkyl, --CN, C.sub.1 -C.sub.18 alkyl-S(.dbd.O).sub.t -- or phenyl-S(.dbd.O).sub.t --;
- R.sub.5 is H, --CH.sub.2 --COOR.sub.13, C.sub.1 -C.sub.4 alkyl or --CN;
- R.sub.6 is H, --COOR.sub.13, C.sub.1 -C.sub.17 alkyl or phenyl;
- R.sub.7 is C.sub.1 -C.sub.18 alkyl;
- C.sub.5 -C.sub.12 cycloalkyl;
- C.sub.3 -C.sub.18 alkenyl;
- phenyl;
- phenyl which is substituted by one to three C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, C.sub.3 -C.sub.8 alkenoxy, halogen or trifluoromethyl radicals;
- phenyl-C.sub.1 -C.sub.4 alkyl;
- C.sub.3 -C.sub.50 alkyl which is interrupted by one or more --O--;
- 1-adamantyl;
- 2-adamantyl;
- norbornyl;
- 2-methylnorbornyl or --C(.dbd.O)--R.sub.12 ;
- R.sub.8 and R.sub.8 ', independently of one another, are H, C.sub.1 -C.sub.18 alkyl, phenyl, phenyl-C.sub.1 -C.sub.8 alkyl, or phenyl substituted by 1 to 3 C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.8 alkenoxy, C.sub.1 -C.sub.8 alkoxy, halogen or CF.sub.3 radicals;
- R.sub.9 is C.sub.1 -C.sub.18 alkyl, phenyl or phenyl-C.sub.1 -C.sub.4 alkyl;
- R.sub.10 is H or --CH.sub.3 ;
- R.sub.11 and R.sub.11 ', independently of one another, are C.sub.1 -C.sub.4 alkyl or phenyl or phenyl which is substituted by one to three C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, C.sub.3 -C.sub.8 alkenoxy, halogen or trifluoromethyl radicals;
- R.sub.12 is H, C.sub.1 -C.sub.18 alkyl, C.sub.2 -C.sub.18 alkenyl, phenyl, phenyl-C.sub.1 -C.sub.4 alkyl, C.sub.5 -C.sub.12 cycloalkyl, C.sub.1 -C.sub.12 alkoxy, phenoxy, norborn-2-yl, 5-norbornen-2-yl or 1-adamantyl;
- R.sub.13 is H, C.sub.1 -C.sub.18 alkyl, C.sub.3 -C.sub.18 alkenyl, phenyl, C.sub.5 -C.sub.12 cycloalkyl, C.sub.3 -C.sub.50 alkyl which is interrupted by one or more --O--, phenyl which is substituted by one to three C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, C.sub.3 -C.sub.8 alkenoxy, halogen or trifluoromethyl radicals, phenyl-C.sub.1 -C.sub.4 alkyl, 1-adamantyl, 2-adamantyl, norbornyl or 2-methylnorbornyl;
- R.sub.14 and R.sub.15, independently of one another, are H, C.sub.1 -C.sub.18 alkyl, C.sub.3 -C.sub.18 alkenyl, C.sub.6 -C.sub.12 cycloalkyl, halogen, CF.sub.3, phenyl, phenyl-C.sub.1 -C.sub.4 alkyl, CN, C.sub.1 -C.sub.18 -alkyl-S(.dbd.O).sub.t --, phenyl-S(.dbd.O).sub.t -- or --OR.sub.131 ;
- R.sub.131 is C.sub.1 -C.sub.18 alkyl, C.sub.3 -C.sub.8 alkenyl, C.sub.1 -C.sub.18 alkyl which is substituted by OH, C.sub.1 -C.sub.18 alkoxy, C.sub.5 -C.sub.12 cycloalkoxy, C.sub.3 -C.sub.6 alkenyloxy, halogen, --COOR.sub.13, --CONH.sub.2, --COHNR.sub.132, --CON(R.sub.132)(R.sub.133), --NHCOR.sub.12, --CN, --OCOR.sub.12, phenoxy and/or by phenoxy which is substituted by C.sub.1 -C.sub.18 alkyl, C.sub.1 -C.sub.18 alkoxy or halogen;
- or is C.sub.3 -C.sub.18 alkenyl;
- C.sub.6 -C.sub.12 cycloalkyl;
- C.sub.1 -C.sub.4 alkyl- and/or --OCOR.sub.12 -substituted C.sub.6 -C.sub.12 cycloalkyl;
- C.sub.3 -C.sub.50 alkyl which is interrupted by one or more --O-- and which is unsubstituted or substituted by OH or O--CO--R.sub.12 ;
- phenyl;
- phenyl-C.sub.1 -C.sub.4 alkyl;
- --COR.sub.12 or --SO.sub.2 R.sub.12 ;
- R.sub.132 and R.sub.133, 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.sub.132 and R.sub.133 together are C.sub.3 -C.sub.9 alkylene, C.sub.3 -C.sub.9 oxaalkylene or -azaalkylene;
- X is --NR.sub.8 --, --O--, --NH--(C.sub.n H.sub.2n)--NH-- or --O--(C.sub.k H.sub.2k)--NH--;
- k is a number from 2 to 4;
- l is a number from 0 to 19;
- m is a number from 2 to 8;
- n is a number from 0 to 4;
- p is a number from 0 to 10;
- q is a number from 1 to 8;
- r is a number from 0 to 18;
- and
- t is the number 0, 1 or 2.
49 more elements
A compound of the formula Ic ##STR70## in which R.sub.1, independently of one another, are ##STR71## --(CH.sub.2).sub.p --SiR.sub.11 RH.sub.11 '--CH.dbd.CH.sub.2, --C(.dbd.O)--(CH.sub.2).sub.q --CH.dbd.CH.sub.2 or --C(.dbd.O)--O--CH.sub.2 --C(.dbd.CH.sub.2)--R.sub.10 ;
- and,
- in the case where R.sub.2 ' is OH or OA, R.sub.1 can additionally be --CH.sub.2 --CH(OA)--CH.sub.2 --O--R.sub.7 ;
- A is --C(.dbd.O)--CR.sub.5 .dbd.CH--R.sub.6 ;
- R.sub.2 and R.sub.2 ', independently of one another, are H, --OH, --OA, C.sub.1 -C.sub.12 alkyl, cyclohexyl, C.sub.3 -C.sub.6 alkenyl, C.sub.1 -C.sub.18 alkoxy, C.sub.2 -C.sub.18 alkenoxy, halogen, phenyl or trifluoromethyl;
- R.sub.3 and R.sub.3 ', independently of one another, are H, --OH, --OA, the abovementioned --OR.sub.1, --O--CHR.sub.8 --(CH.sub.2).sub.l --OA, --O--CH.sub.2 --CH(OA)--R.sub.9, --O--CH.sub.2 --CH(OH)--CH.sub.2 --OA, --O--CHR.sub.8 --(CH.sub.2).sub.r --C(.dbd.O)--O--CH.sub.2 --CH(OH)--CH.sub.2 --OA, C.sub.1 -C.sub.12 alkyl, cyclohexyl, C.sub.3 -C.sub.6 alkenyl, C.sub.1 -C.sub.18 alkoxy, C.sub.3 -C.sub.18 alkenoxy, halogen, trifluoromethyl, phenyl, phenoxy, phenyl-C.sub.1 -C.sub.4 alkyl, phenyl-C.sub.1 -C.sub.4 alkoxy, --CN, C.sub.1 -C.sub.18 alkyl-S(.dbd.O).sub.t -- or phenyl-S(.dbd.O).sub.t --;
- R.sub.4, R.sub.4 ' and R.sub.4 ", independently of one another, are H, C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.1 -C.sub.18 alkoxy, C.sub.3 -C.sub.18 alkenoxy, halogen, trifluoromethyl, phenyl, phenoxy, phenyl-C.sub.1 -C.sub.4 alkyl, mono- to tri-C.sub.1 -C.sub.4 alkyl-substituted phenyl-C.sub.1 -C.sub.4 alkyl, phenyl-C.sub.1 -C.sub.4 alkoxy, --CN, C.sub.1 -C.sub.18 alkyl-S(.dbd.O).sub.t -- or phenyl-S(.dbd.O).sub.t --;
- R.sub.5 is H, --CH.sub.2 --COOR.sub.13, C.sub.1 -C.sub.4 alkyl or --CN;
- R.sub.6 is H, --COOR.sub.13, C.sub.1 -C.sub.17 alkyl or phenyl;
- R.sub.7 is C.sub.1 -C.sub.18 alkyl, cyclohexyl, C.sub.3 -C.sub.18 alkenyl, phenyl, phenyl which is substituted by one to three C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, C.sub.2 -C.sub.8 alkenoxy, halogen or trifluoromethyl radicals, phenyl-C.sub.1 -C.sub.4 alkyl or --C(.dbd.O)--R.sub.12 ;
- R.sub.8 is H or C.sub.1 -C.sub.18 alkyl;
- R.sub.9 is C.sub.1 -C.sub.18 alkyl, phenyl or phenyl-C.sub.1 -C.sub.4 alkyl;
- R.sub.10 is H or --CH.sub.3 ;
- R.sub.11 and R.sub.11 ', independently of one another, are C.sub.1 -C.sub.4 alkyl or phenyl or phenyl which is substituted by one to three C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, C.sub.3 -C.sub.8 alkenoxy, halogen or trifluoromethyl radicals;
- R.sub.12 is C.sub.1 -C.sub.18 alkyl, C.sub.2 -C.sub.18 alkenyl or phenyl;
- R.sub.13 is H, C.sub.1 -C.sub.18 alkyl, C.sub.3 -C.sub.18 alkenyl or phenyl;
- l is a number from 0 to 19;
- p is a number from 0 to 10;
- q is a number from 1 to 8;
- r is a number from 0 to 18;
- and
- t is the number 0, 1 or 2.
18 more elements
Dependencies are inferred from the claim text.