US 5,112,977 AGranted

Substituted naphthacene-5,12-diones

AssigneeCiba-Geigy Corporation

InventorsWalter Fischer, Marcus Baumann, Jurgen Finter, Vratislav Kvita, Carl W. Mayer, Wolfgang Wernet

Life of this patent

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Abstract

Substituted naphthacenediones of the formula I ##STR1## in which R.sup.1 to R.sup.8 are H and at least one of R.sup.1 to R.sup.8, for example R.sup.2 and R.sup.3 or R.sup.2 and R.sup.6, are, for example, C.sub.1 -C.sub.20 alkoxy, C.sub.1 -C.sub.20 alkenoxy, C.sub.1 -C.sub.20 -alkylsulfinyl, --CN, --CF.sub.3, --NO.sub.2, --Si(CH.sub.3).sub.3 or --COO(C.sub.1 -C.sub.12 alkyl), are suitable, when incorporated into polymers having hydroxyalkyl groups, for currentless deposition of metals onto the polymer surface. They are in some cases suitable as photoinitiators.

Claims9

Dependent claims

A compound of the formula I ##STR40## wherein (a) R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are H and R.sup.5 to R.sup.6 are each H and at least one of the radicals R.sup.5 to R.sup.8, independently of one another, is a substituent selected from the group consisting of C.sub.1 -C.sub.20 alkyl-(X).sub.p --, with the exception of methyl and methoxy, C.sub.2 -C.sub.18 alkenyl-(X).sub.p --, C.sub.2 -C.sub.18 alkynyl-(X).sub.p --, C.sub.3 -C.sub.8 cycloalkyl-(X).sub.p --, (C.sub.1 -C.sub.12 alkyl)-C.sub.3 -C.sub.8 cycloalkyl-(X).sub.p --, C.sub.3 -C.sub.8 cycloalkyl-C.sub.r H.sub.2r --(X).sub.p --, (C.sub.1 -C.sub.12 alkyl)-C.sub.3 -C.sub.8 cycloalkyl-C.sub.r H.sub.2r --(X).sub.p --, phenyl-(X).sub.p --, (C.sub.1 -C.sub.12 alkyl)phenyl-(X).sub.p --, phenyl-C.sub.r H.sub.2r --(X).sub.p -- and (C.sub.1 -C.sub.12 alkyl)phenyl-C.sub.r H.sub.2r --(X).sub.p --, which are unsubstituted or substituted by halogen, --CN, furfuryl, --NR.sup.9 R.sup.10, -- OR.sup.9, --SR or --COOR.sup.9 wherein r is 1 or 2, p is 0 or 1 and X is --O--, --SO-- or --SO.sub.2 --, or R.sup.5 to R.sup.8 independently are a substituent selected from the group consisting of halogen, --NO.sub.2, --CF.sub.3, --CN, --NR.sup.9 R.sup.10, --COOR.sup.9, --CONR.sup.9 R.sup.10, --COCl, --SH, --Si(C.sub.1 -C.sub.4 alkyl).sub.3 and --O--(C.sub.m H.sub.2m --O--).sub.n R.sup.11, or in each case two adjacent radicals from R.sup.5 to R.sup.8 together are --CO--O--CO-- or --CO--NR.sup.9 --CO--, R.sup.9 and R.sup.10 independently of one another are H, C.sub.1 -C.sub.12 alkyl, phenyl or (--C.sub.m H.sub.2m --O--).sub.q R.sup.11, or R.sup.9 and R.sup.10 together are tetramethylene, pentamethylene, 3-oxapentylene or --CH.sub.2 CH.sub.2 NR.sup.9 CH.sub.2 CH.sub.2 --, R.sup.11 is H or C.sub.1 -C.sub.12 alkyl, m is a number from 2 to 4, n is a number from 2 to 20 and q is a number from 1 to 20, or

b) R.sup.1 to R.sup.8 independently of one another are H or a substituent selected from the group consisting of C.sub.1 -C.sub.20 alkyl-(X).sub.p --, C.sub.2 -C.sub.18 alkenyl-(X).sub.p --, C.sub.2 -C.sub.18 alkynyl-(X).sub.p --, C.sub.3 -C.sub.8 cycloalkyl-(X).sub.p --, (C.sub.1 -C.sub.12 alkyl)-C.sub.3 -C.sub.8 cycloalkyl-(X).sub.p --, C.sub.3 -C.sub.8 cycloalkyl-C.sub.r H.sub.2r --(X).sub.p --, (C.sub.1 -C.sub.12 alkyl)-C.sub.3 -C.sub.8 cycloalkyl-C.sub.r H.sub.2r --(X).sub.p --, phenyl-(X).sub.p --, (C.sub.1 -C.sub.12 alkyl)phenyl-(X).sub.p --, phenyl-C.sub.r H.sub.2r --(X).sub.p -- and (C.sub.1 -C.sub.12 alkyl)phenyl-C.sub.r H.sub.2r --(X).sub.p --, which are unsubstituted or substituted by halogen, --CN, furfuryl, --NR.sup.9 R.sup.10, --OR.sup.9, --SR or --COOR.sup.9 wherein r is 1 or 2, p is 0 or 1 and X is --O--, --SO-- or --SO.sub.2 -- wherein X is also --S-- for R.sup.1 to R.sup.4, R.sup.5 and R.sup.8 ;
or R.sup.1 to R.sup.8 are a substituent selected from the group consisting of halogen, --NO.sub.2, --CF.sub.3, --CN, --NR.sup.9 R.sup.10, --COOR.sup.9, --CONR.sup.9 R.sup.10, --COCl, --SH, --Si(C.sub.1 -C.sub.4 alkyl).sub.3 and --O--(C.sub.m H.sub.2m --O--).sub.n R.sup.11 or R.sup.5 to R.sup.8 are a pair of adjacent substituents which are --CO--O--CO-- or --CO--NR.sup.9 --CO--;
R.sup.9 and R.sup.10 independently of one another are H, C.sub.1 -C.sub.12 alkyl, phenyl or (--C.sub.m H.sub.2m --O--).sub.q R.sup.11, or R.sup.9 and R.sup.10 together are tetramethylene, pentamethylene, 3-oxapentylene or --CH.sub.2 CH.sub.2 NR.sup.9 CH.sub.2 CH.sub.2 --, R.sup.11 is H or C.sub.1 -C.sub.12 alkyl, m is a number from 2 to 4, n is a number from 2 to 20 and q is a number from 1 to 20, wherein at least one of R.sup.1 to R.sup.4 and R.sup.5 to R.sup.8 is a substituent, provided that R.sup.2 and R.sup.6 or R.sup.7 are not F and that 2-ethoxy-7-methoxyanthracen-5,12-dione and 2-ethoxy-10-methoxyanthracen-5,12-dione are excluded.

Dependencies are inferred from the claim text.

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Abstract

b) R.sup.1 to R.sup.8 independently of one another are H or a substituent selected from the group consisting of C.sub.1 -C.sub.20 alkyl-(X).sub.p --, C.sub.2 -C.sub.18 alkenyl-(X).sub.p --, C.sub.2 -C.sub.18 alkynyl-(X).sub.p --, C.sub.3 -C.sub.8 cycloalkyl-(X).sub.p --, (C.sub.1 -C.sub.12 alkyl)-C.sub.3 -C.sub.8 cycloalkyl-(X).sub.p --, C.sub.3 -C.sub.8 cycloalkyl-C.sub.r H.sub.2r --(X).sub.p --, (C.sub.1 -C.sub.12 alkyl)-C.sub.3 -C.sub.8 cycloalkyl-C.sub.r H.sub.2r --(X).sub.p --, phenyl-(X).sub.p --, (C.sub.1 -C.sub.12 alkyl)phenyl-(X).sub.p --, phenyl-C.sub.r H.sub.2r --(X).sub.p -- and (C.sub.1 -C.sub.12 alkyl)phenyl-C.sub.r H.sub.2r --(X).sub.p --, which are unsubstituted or substituted by halogen, --CN, furfuryl, --NR.sup.9 R.sup.10, --OR.sup.9, --SR or --COOR.sup.9 wherein r is 1 or 2, p is 0 or 1 and X is --O--, --SO-- or --SO.sub.2 -- wherein X is also --S-- for R.sup.1 to R.sup.4, R.sup.5 and R.sup.8 ;
or R.sup.1 to R.sup.8 are a substituent selected from the group consisting of halogen, --NO.sub.2, --CF.sub.3, --CN, --NR.sup.9 R.sup.10, --COOR.sup.9, --CONR.sup.9 R.sup.10, --COCl, --SH, --Si(C.sub.1 -C.sub.4 alkyl).sub.3 and --O--(C.sub.m H.sub.2m --O--).sub.n R.sup.11 or R.sup.5 to R.sup.8 are a pair of adjacent substituents which are --CO--O--CO-- or --CO--NR.sup.9 --CO--;
R.sup.9 and R.sup.10 independently of one another are H, C.sub.1 -C.sub.12 alkyl, phenyl or (--C.sub.m H.sub.2m --O--).sub.q R.sup.11, or R.sup.9 and R.sup.10 together are tetramethylene, pentamethylene, 3-oxapentylene or --CH.sub.2 CH.sub.2 NR.sup.9 CH.sub.2 CH.sub.2 --, R.sup.11 is H or C.sub.1 -C.sub.12 alkyl, m is a number from 2 to 4, n is a number from 2 to 20 and q is a number from 1 to 20, wherein at least one of R.sup.1 to R.sup.4 and R.sup.5 to R.sup.8 is a substituent, provided that R.sup.2 and R.sup.6 or R.sup.7 are not F and that 2-ethoxy-7-methoxyanthracen-5,12-dione and 2-ethoxy-10-methoxyanthracen-5,12-dione are excluded.