US 5,391,749 AGranted

Substituted naphthacene-5,12-diones and their use

AssigneeCiba-Geigy Corporation

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

Life of this patent

Estimating the term…

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.

Claims10

Dependent claims

A compound of the formula ##STR39## wherein (a) R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are H, and

(a1) R.sub.1 and R.sub.4 are independently of each other selected from the group consisting of H, --NO.sub.2, --CF.sub.3, --CN, COOR.sub.9, --CONR.sub.9 R.sub.10, --COCl, --Si(C.sub.1 -C.sub.4 alkyl).sub.3, --S(C.sub.m H.sub.2m --O--).sub.n R.sub.11, --O(C.sub.m H.sub.2m --O--).sub.n R.sub.11, substituted or unsubstituted C.sub.1 -C.sub.20 alkyl-(X.sub.1 --).sub.p, C.sub.2 -C.sub.18 alkenyl-(X.sub.1 --).sub.p, C.sub.2 -C.sub.18 alkynyl-(X.sub.1 --).sub.p, C.sub.3 -C.sub.8 cycloalkyl-(X.sub.1 --).sub.p, (C.sub.1 -C.sub.12 alkyl)C.sub.3 -C.sub.8 cycloalkyl-(X.sub.1 --).sub.p, C.sub.3 -C.sub.8 cycloalkylC.sub.r H.sub.2r -(X.sub.1 --).sub.p, (C.sub.1 -C.sub.12 alkyl)C.sub.3 -C.sub.8 cycloalkyl C.sub.r H.sub.2r --(X.sub.1 --).sub.p, phenyl-(X.sub.1 --).sub.p,(C.sub.1 -C.sub.12 alkyl)phenyl-(X.sub.1 --).sub.p, phenylC.sub.r H.sub.2r --(X--).sub. p, (C.sub.1 -C.sub.12 alkyl)phenylC.sub.r H.sub.2r --(X--).sub.p, substituted C.sub.1 -C.sub.20 alkylthio and phenyloxy, (C.sub.1 -C.sub.12 alkyl)phenyloxy or C.sub.1 -C.sub.20 alkoxy which is substituted by halogen, --CN, --NR.sub.9 R.sub.10, --SR.sub.9, --OR.sub.9 or --COOR.sub.9, wherein R.sub.1 is additionally selected from the group consisting of unsubstituted C.sub.1 -C.sub.20 alkylthio, phenyloxy, phenylthio, C.sub.1 -C.sub.12 alkylphenyloxy and substituted C.sub.1 -C.sub.12 alkylphenylthio;
and
(a2) R.sub.2 and R.sub.3 each are independently selected from the group consisting of H, substituted C.sub.5 -C.sub.20 -alkyl, unsubstituted C.sub.8 -C.sub.18 alkoxy, substituted C.sub.3 -C.sub.20 alkoxy, unsubstituted or substituted C.sub.1 -C.sub.20 alkyl-(X.sub.1 --).sub.p --, phenyl-(X).sub.p --, (C.sub.1 -C.sub.12 alkyl)phenyl-(X--).sub.p, phenylC.sub.r H.sub.2r --(X--).sub.p, (C.sub.1 -C.sub.12 alkyl)phenylC.sub.r H.sub.2r --(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 cycloalkylC.sub.r H.sub.2r --(X--).sub.p --, and (C.sub.1 -C.sub.12 alkyl)C.sub.3 -C.sub.8 cycloalkylC.sub.r H.sub.2r --(X--).sub.p, or
(a3) one of R.sub.2 and R.sub.3 or both of R.sub.2 and R.sub.3 are selected from the group consisting of C.sub.1 -C.sub.4 alkyl which is substituted by halogen, --CN, --NR.sub.9 R.sub.10, --SR.sub.9, --OR.sub.9 or --COOR.sub.9 and C.sub.1 -C.sub.2 -alkoxy which is substituted by halogen, --CN, --NR.sub.9 R.sub.10, --SR.sub.9, --OR.sub.9 --COOR.sub.9, or
(a4) one of R.sub.2 and R.sub.3 or both of R.sub.2 and R.sub.3 are selected from the group consisting of --SH, --NO.sub.2, --CF.sub.3, --NR.sub.9 R.sub.10, --O(C.sub.m H.sub.2m --O--).sub.n R.sub.11, and --Si(C.sub.1 -C.sub.4 alkyl).sub.3, or
(a5) one of R.sub.2 and R.sub.3 is halogen, --COOR.sub.9 --NR.sub.9 R.sub.10 or COCl and the other of R.sub.2 and R.sub.3 is selected from the group consisting of --NO.sub.2, --CF.sub.3, --CN, --NR.sub.9 R.sub.10, --SH, --O(C.sub.m H.sub.2m --O--).sub.n R.sub.11, --Si(C.sub.1 -C.sub.4 alkyl).sub.3, 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 cycloalkylC.sub.r H.sub.2r --(X--).sub.p, (C.sub.1 -C.sub.12 alkyl)C.sub.3 -C.sub.8 cycloalkylC.sub.r H.sub.2r --(X--).sub.p, phenyl-(X--).sub.p, (C.sub.1 -C.sub.12 alkyl)phenyl-(X--).sub.p, phenylC.sub.r H.sub.2r --(X--).sub.p, and (C.sub.1 -C.sub.12 alkyl)phenylC.sub.r H.sub.2r --(X-- ).sub.p, which are unsubstituted or substituted, or the other of R.sub.2 and R.sub.3 is H, if at least one or R.sub.1 and R.sub.4 is not hydrogen, or
(a6) R.sub.2 and R.sub.3 together are --CO--O--CO-- or --CO--NR.sub.9 --CO-- and at least one of R.sub.1 and R.sub.4 is not hydrogen;
and wherein
X.sub.1 is --SO-- or --SO.sub.2 -- and X is --O--, --SO-- or --SO.sub.2 --;
R.sub.9 and R.sub.10 independently of one another are C.sub.1 -C.sub.12 alkyl, phenyl or (--C.sub.m H.sub.2m --O--).sub.q R.sub.11, or R.sub.9 and R.sub.10 together are tetramethylene, pentamethylene, 3-oxapentylene or --CH.sub.2 CH.sub.2 NR.sub.9 CH.sub.2 CH.sub.2 --, R.sub.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, p is 1, q is a number from 1 to 20 and r is 1 or 2;
and wherein
substituted R.sub.1, R.sub.2, R.sub.3 and R.sub.4 groups are substituted by halogen, --CN, furfuryl, --NR.sub.9 R.sub.10, --OR.sub.9, --SR.sub.9 or COOR.sub.9 unless otherwise specified;
with the provisos that at least one of R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is other than hydrogen.

10 more elements

Dependencies are inferred from the claim text.

Facts

Application: 07/843,656Filed 28 Feb 1992 · division
Priority: CH 2008/8827 May 1988
Granted: 21 Feb 1995
Term ends: Not estimatedThe source records don’t support an estimate.

Classification32 codes

C07D 295/116
With the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by…: with…
B05D 1/202
Substances to be applied floating on a fluid: langmuir Blodgett films
B82Y 30/00
Nanotechnology for materials or surface science
B82Y 40/00
Manufacture or treatment of nanostructures

Family

Serial356,830Parent of this division · filed 24 May 1989
US 5,112,977 AParent of this division
US 5,391,749 AThis patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A compound of the formula ##STR39## wherein (a) R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are H, and

(a1) R.sub.1 and R.sub.4 are independently of each other selected from the group consisting of H, --NO.sub.2, --CF.sub.3, --CN, COOR.sub.9, --CONR.sub.9 R.sub.10, --COCl, --Si(C.sub.1 -C.sub.4 alkyl).sub.3, --S(C.sub.m H.sub.2m --O--).sub.n R.sub.11, --O(C.sub.m H.sub.2m --O--).sub.n R.sub.11, substituted or unsubstituted C.sub.1 -C.sub.20 alkyl-(X.sub.1 --).sub.p, C.sub.2 -C.sub.18 alkenyl-(X.sub.1 --).sub.p, C.sub.2 -C.sub.18 alkynyl-(X.sub.1 --).sub.p, C.sub.3 -C.sub.8 cycloalkyl-(X.sub.1 --).sub.p, (C.sub.1 -C.sub.12 alkyl)C.sub.3 -C.sub.8 cycloalkyl-(X.sub.1 --).sub.p, C.sub.3 -C.sub.8 cycloalkylC.sub.r H.sub.2r -(X.sub.1 --).sub.p, (C.sub.1 -C.sub.12 alkyl)C.sub.3 -C.sub.8 cycloalkyl C.sub.r H.sub.2r --(X.sub.1 --).sub.p, phenyl-(X.sub.1 --).sub.p,(C.sub.1 -C.sub.12 alkyl)phenyl-(X.sub.1 --).sub.p, phenylC.sub.r H.sub.2r --(X--).sub. p, (C.sub.1 -C.sub.12 alkyl)phenylC.sub.r H.sub.2r --(X--).sub.p, substituted C.sub.1 -C.sub.20 alkylthio and phenyloxy, (C.sub.1 -C.sub.12 alkyl)phenyloxy or C.sub.1 -C.sub.20 alkoxy which is substituted by halogen, --CN, --NR.sub.9 R.sub.10, --SR.sub.9, --OR.sub.9 or --COOR.sub.9, wherein R.sub.1 is additionally selected from the group consisting of unsubstituted C.sub.1 -C.sub.20 alkylthio, phenyloxy, phenylthio, C.sub.1 -C.sub.12 alkylphenyloxy and substituted C.sub.1 -C.sub.12 alkylphenylthio;
and
(a2) R.sub.2 and R.sub.3 each are independently selected from the group consisting of H, substituted C.sub.5 -C.sub.20 -alkyl, unsubstituted C.sub.8 -C.sub.18 alkoxy, substituted C.sub.3 -C.sub.20 alkoxy, unsubstituted or substituted C.sub.1 -C.sub.20 alkyl-(X.sub.1 --).sub.p --, phenyl-(X).sub.p --, (C.sub.1 -C.sub.12 alkyl)phenyl-(X--).sub.p, phenylC.sub.r H.sub.2r --(X--).sub.p, (C.sub.1 -C.sub.12 alkyl)phenylC.sub.r H.sub.2r --(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 cycloalkylC.sub.r H.sub.2r --(X--).sub.p --, and (C.sub.1 -C.sub.12 alkyl)C.sub.3 -C.sub.8 cycloalkylC.sub.r H.sub.2r --(X--).sub.p, or
(a3) one of R.sub.2 and R.sub.3 or both of R.sub.2 and R.sub.3 are selected from the group consisting of C.sub.1 -C.sub.4 alkyl which is substituted by halogen, --CN, --NR.sub.9 R.sub.10, --SR.sub.9, --OR.sub.9 or --COOR.sub.9 and C.sub.1 -C.sub.2 -alkoxy which is substituted by halogen, --CN, --NR.sub.9 R.sub.10, --SR.sub.9, --OR.sub.9 --COOR.sub.9, or
(a4) one of R.sub.2 and R.sub.3 or both of R.sub.2 and R.sub.3 are selected from the group consisting of --SH, --NO.sub.2, --CF.sub.3, --NR.sub.9 R.sub.10, --O(C.sub.m H.sub.2m --O--).sub.n R.sub.11, and --Si(C.sub.1 -C.sub.4 alkyl).sub.3, or
(a5) one of R.sub.2 and R.sub.3 is halogen, --COOR.sub.9 --NR.sub.9 R.sub.10 or COCl and the other of R.sub.2 and R.sub.3 is selected from the group consisting of --NO.sub.2, --CF.sub.3, --CN, --NR.sub.9 R.sub.10, --SH, --O(C.sub.m H.sub.2m --O--).sub.n R.sub.11, --Si(C.sub.1 -C.sub.4 alkyl).sub.3, 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 cycloalkylC.sub.r H.sub.2r --(X--).sub.p, (C.sub.1 -C.sub.12 alkyl)C.sub.3 -C.sub.8 cycloalkylC.sub.r H.sub.2r --(X--).sub.p, phenyl-(X--).sub.p, (C.sub.1 -C.sub.12 alkyl)phenyl-(X--).sub.p, phenylC.sub.r H.sub.2r --(X--).sub.p, and (C.sub.1 -C.sub.12 alkyl)phenylC.sub.r H.sub.2r --(X-- ).sub.p, which are unsubstituted or substituted, or the other of R.sub.2 and R.sub.3 is H, if at least one or R.sub.1 and R.sub.4 is not hydrogen, or
(a6) R.sub.2 and R.sub.3 together are --CO--O--CO-- or --CO--NR.sub.9 --CO-- and at least one of R.sub.1 and R.sub.4 is not hydrogen;
and wherein
X.sub.1 is --SO-- or --SO.sub.2 -- and X is --O--, --SO-- or --SO.sub.2 --;
R.sub.9 and R.sub.10 independently of one another are C.sub.1 -C.sub.12 alkyl, phenyl or (--C.sub.m H.sub.2m --O--).sub.q R.sub.11, or R.sub.9 and R.sub.10 together are tetramethylene, pentamethylene, 3-oxapentylene or --CH.sub.2 CH.sub.2 NR.sub.9 CH.sub.2 CH.sub.2 --, R.sub.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, p is 1, q is a number from 1 to 20 and r is 1 or 2;
and wherein
substituted R.sub.1, R.sub.2, R.sub.3 and R.sub.4 groups are substituted by halogen, --CN, furfuryl, --NR.sub.9 R.sub.10, --OR.sub.9, --SR.sub.9 or COOR.sub.9 unless otherwise specified;
with the provisos that at least one of R.sub.1, R.sub.2, R.sub.3 or R.sub.4 is other than hydrogen.

10 more elements

Facts

Application

07/843,656Filed 28 Feb 1992 · division

Priority

CH 2008/8827 May 1988

Granted

21 Feb 1995

Term ends

Not estimatedThe source records don’t support an estimate.

Classification32 codes

C07D 295/116
With the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by…: with…
B05D 1/202
Substances to be applied floating on a fluid: langmuir Blodgett films
B82Y 30/00
Nanotechnology for materials or surface science
B82Y 40/00
Manufacture or treatment of nanostructures