Process for the quenching of fluorescence, and new cationic naphthalene-peri-dicarboxylic acid imide derivatives

Claim 2

A process for the quenching of the fluorescence created by anionic optical brighteners said process comprising adding a substrate containing said optical brighteners virtually colorless, water-soluble, cationic compounds, wherein said compounds contain at least one cationic group per molecule and at least two naphthalene-peri-dicarboxylic acid imide groups which are nitro group free per molecule.

Claim 3

A process according to claim 1 wherein the compounds have the formula ##STR577## in which A 1 , A 2 and W represent a bridging member or a single bond, W also represents hydrogen, E.sup.⊕ represents a terminal ammonium or sulphonium group, K.sup.⊕ represents a doubly bridging ammonium or sulphonium group, An.sup.⊖ represents an anion, m and k represent 1 or 2, z represents 0, 1, 2, 3 or 4, n represents 0 or 1 and p represents 1, 2 or 3, q corresponds to the sum of the free cationic charges, where n+z≠0, in which the naphthalene ring can also be substituted in the second peri-position by --CH 2 --CH 2 --, --CO--O--CO-- or --CO--NH--CO--, the naphthalene ring system, A 1 , A 2 , W, -E⊕ and -K⊕-and the second peridicarboxlic acid imide nitrogen atom can be substituted by non-ionic radicals.

Claim 4

A process according to claim 2, wherein the compounds have the formula ##STR578## in which T 4 and T 5 together represent a --CO--N(T 6 )--CO-- group, T 6 represents hydrogen, OH, C 1 -C 6 -alkyl which is optionally substituted by 1 to 2 OH groups, chlorine, C 1 -C 4 -alkoxy or COOH, allyl, phenyl or benzyl which can be substituted by 1 or 2 C 1 -C 4 -alkyl, chlorine, C 1 -C 2 -alkoxy, bromine, carboxy, cyano, C 1 -C 2 -alkoxycarbonyl, C 1 -C 2 -alkylsulphonyl, carbamoyl or sulphamoyl, β-aminoethylphenyl, pyridyl-(2)-or-(3)-,benzothiazol-(2)-yl, 1,2,4-triazol-3-yl, cyclohexyl, -A 5 -E 2 ⊕ or, in the case where m=1, n=0 and p=1, represents a grouping of the formula -A 5 -K 2 ⊕-A 6 - or -A 5 -K 2 ⊕-A 6 -W 2 -A 6 -K 2 ⊕-A 5 - A 5 and A 6 or the two radicals A 5 being bonded to 2 different 1,4,5,8-naphthalene tetracarboxylic acid diimide molecules, A 5 represents a single bond, C 1 -C 5 -alkylene, m- or p-C 6 H 4 -CH 2 -, A 6 represents a single bond, --CH 2 --, --CH 2 --CO--O--, --CH 2 --CO--N(R)--, --CH 2 --SO 2 --N(R)--, --(CH 2 ) 2 --CO--N(R)--, --CH 2 --CO--NH--CH 2 --, C 1 -C 5 -alkylene--N(R)--CO--, C 1 -C 5 -alkylene-N(R)--SO 2 --, C 1 -C 5 -alkylene--N(R)--CO--NH--, --CH 2 --C 6 H 4 --NH--CO--, --CH 2 --C 6 H 4 --NH--SO 2 --, --CH 2 --C 6 H 4 --NH--CO--NH--, --(CH 2 ) w --CO--, --(CH 2 ) w --CO--C 6 H 4 --NH--CO--, --(CH 2 ) w --CO--C 6 H 4 --NH--SO 2 --, --(CH 2 ) w --CO--C 6 H 4 --NH--CO--NH--, in addition: --SO 2 --, --CO-- or --CONH--, when K 2 ⊕=piperazinium, and --NH--CO--NH--, when K 2 ⊕=pyridinium, K 2 ⊕ represents ##STR579## -E 2 ⊕ represents ##STR580## R 4 and R 5 each represent C 1 -C 4 -alkyl, which can be substituted by OH, CONH 2 , C 1 -C 2 -alkoxycarbonyl or C 1 -C 2 -alkylcarbonyl, or allyl, R 4 , in addition, represents hydrogen, cyclohexyl, benzoyl- or benzoylmethyl radicals, which can be substituted on the nucleus by 1 or 2 radicals from the series comprising methyl, chlorine, methoxy, ethoxy, cyano, C 1 -C 2 -alkoxycarbonyl or nitro, or benzimidazol-2-ylmethyl, R 5 , in addition, represents benzyl or one radical R 5 in each case also represents phenyl, W 2 represents --CO--, a p-bonded benzene, naphthalene, cyclohexane, piperazine, thiophene-(2,5)-, 1,3,4-oxadiazole-(2,5)-, s-triazine,-(2,4 or 2,4,6) radical or a radical of the formulae ##STR581## in which, in the case where p=1, one of the specified free valences is saturated by hydrogen, D 4 and D 5 each represent CH 2 , a C 2 -C 5 -alkylene which is optionally interrupted by --O--, --O--, --N(R)--, --O--C 2 -C 4 -alkylene--O-- or a radical of the formula ##STR582## where D 6 =Cl, OR, -N(R 4 R 5 ), ##STR583## D 4 , in addition, represents 1,1-cyclohexylene, p-phenylene, --CH(C 6 H 5 )--, --CH(C 6 H 4 --)--, --S--, --SO 2 --, --CO--NH--, --NH--CO--NH--, ##STR584## or a single bond, it being possible for the rings mention in D 4 , D 5 , and also in W 2 , to be substituted by CH 3 , CH 3 O or Cl, in which, in the case where p=2, the grouping -K 2 ⊕-A 6 -W 2 - A 6 -K 2 ⊕- as a whole can also represent ##STR585## in which the indices m and p only denote 1 simultaneously when T 4 and T 5 form a cyclic peridicarboxylic acid imide grouping, and in which n can only be zero when T 6 contains a cationic group -K 2 ⊕- or -E 2 ⊕.

Claim 5

A process according to claim 3, wherein the compounds have the formula ##STR586## with T 7 T 8 =hydrogen, chlorine or bromine, r=2 or 3, in which the radicals A 6 and --when m=2--the radicals A 5 can be different from one another.

Claim 6

A process according to claim 4, wherein the compounds correspond to the formula ##STR587## .