US 5,744,599 AGranted

Triazinyldiaminostilbene compounds useful as ultraviolet absorbers and as fluorescent whitening agents

AssigneeCiba Specialty Chemicals Corporation

InventorsDieter Reinehr, Claude Eckhardt, Robert Hochberg, Werner Kaufmann, Georges Metzger

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Abstract

The present invention relates to new compounds which are useful as ultraviolet absorbing agents (UVAs) and as fluorescent whitening agents (FWAs), and to a method of improving the sun protection factor (SPF) of textile fibre material, especially cotton, polyamide and wool, treated with the new compounds and with certain known compounds.

Claims19

Dependent claims

A compound having the formula:

##STR27## in which M is hydrogen, an alkali metal cation, ammonium or a cation formed from an amine;
R.sub.1 is a group having one of the formulae:
##STR28## in which R.sub.3 is unsubstituted alkyl or alkyl substituted by one or more halogen, C.sub.1 -C.sub.4 -alkoxy, phenyl, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, mono- or di-C.sub.1 -C.sub.4 alkylated amino or --SO.sub.3 M groups or unsubstituted aryl or aryl substituted by one or more C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, C.sub.2 -C.sub.5 -alkanoylamino, nitro, sulpho or di-C.sub.1 -C.sub.4 alkylated amino groups;
##STR29## in which R.sub.4 is M, unsubstituted alkyl or alkyl substituted by one or more halogen, C.sub.1 -C.sub.4 -alkoxy, phenyl, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, mono- or di-C.sub.1 -C.sub.4 alkylated amino or --SO.sub.3 M groups or unsubstituted aryl or aryl substituted by one or more C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, C.sub.2 -C.sub.5 -alkanoylamino, nitro, sulpho or di-C.sub.1 -C.sub.4 alkylated amino groups ##STR30## in which R.sub.5 is hydrogen, unsubstituted alkyl or alkyl substituted by one or more halogen, C.sub.1 -C.sub.4 -alkoxy, phenyl, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, mono- or di-C.sub.1 -C.sub.4 alkylated amino or --SO.sub.3 M groups or unsubstituted aryl or aryl substituted by one or more C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, C.sub.2 -C.sub.5 -alkanoylamino, nitro, sulpho or di-C.sub.1 -C.sub.4 alkylated amino groups or --NR.sub.7 R.sub.8 in which R.sub.7 and R.sub.8, independently, are hydrogen, unsubstituted alkyl or alkyl substituted by one or more halogen, C.sub.1 -C.sub.4 -alkoxy, phenyl, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, mono- or di-C.sub.1 -C.sub.4 alkylated amino or --SO.sub.3 M groups or unsubstituted aryl or aryl substituted by one or more C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, C.sub.2 -C.sub.5 -alkanoylamino, nitro, sulpho or di-C.sub.1 -C.sub.4 alkylated amino groups, or R.sub.7 and R.sub.8, together with the nitrogen atom to which they are attached, form a morpholine or piperidine ring;
##STR31## in which R.sub.5 is hydrogen, unsubstituted alkyl or alkyl substituted by one or more halogen, C.sub.1 -C.sub.4 -alkoxy, phenyl, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, mono- or di-C.sub.1 -C.sub.4 alkylated amino or --SO.sub.3 M groups or unsubstituted aryl or aryl substituted by one or more C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, C.sub.2 -C.sub.5 -alkan-oylamino, nitro, sulpho or di-C.sub.1 -C.sub.4 alkylated amino groups, provided that R.sub.5 is not carboxymethyl or hydroxymethyl;
R.sub.2 is hydrogen, unsubstituted alkyl or alkyl substituted by one or more halogen, C.sub.1 -C.sub.4 -alkoxy, phenyl, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, mono- or di-C.sub.1 -C.sub.4 alkylated amino or --SO.sub.3 M groups or unsubstituted aryl or aryl substituted by one or more C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, C.sub.2 -C.sub.5 -alkanoylamino, nitro, sulpho or di-C.sub.1 -C.sub.4 alkylated amino groups, ##STR32## --OH,--NH.sub.2,--N(CH.sub.2 CH.sub.2 OH).sub.2, --NCH.sub.2 CH(OH)CH.sub.3 !.sub.2,--NH--R.sub.4,--N(R.sub.4).sub.2 or --OR.sub.4, in which R.sub.4 has its previous significance;
and n.sub.1 and n.sub.2, independently, are 0 or 1, provided that the compounds in which n.sub.1 and n.sub.2 are each 1, R.sub.1 is ##STR33## in which R.sub.3 or R.sub.4 is unsubstituted alkyl and R.sub.2 is --OR.sub.4 in which R.sub.4 is naphthyl are excluded.

4 more elements

Dependencies are inferred from the claim text.

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Abstract

A compound having the formula:

##STR27## in which M is hydrogen, an alkali metal cation, ammonium or a cation formed from an amine;
R.sub.1 is a group having one of the formulae:
##STR28## in which R.sub.3 is unsubstituted alkyl or alkyl substituted by one or more halogen, C.sub.1 -C.sub.4 -alkoxy, phenyl, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, mono- or di-C.sub.1 -C.sub.4 alkylated amino or --SO.sub.3 M groups or unsubstituted aryl or aryl substituted by one or more C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, C.sub.2 -C.sub.5 -alkanoylamino, nitro, sulpho or di-C.sub.1 -C.sub.4 alkylated amino groups;
##STR29## in which R.sub.4 is M, unsubstituted alkyl or alkyl substituted by one or more halogen, C.sub.1 -C.sub.4 -alkoxy, phenyl, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, mono- or di-C.sub.1 -C.sub.4 alkylated amino or --SO.sub.3 M groups or unsubstituted aryl or aryl substituted by one or more C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, C.sub.2 -C.sub.5 -alkanoylamino, nitro, sulpho or di-C.sub.1 -C.sub.4 alkylated amino groups ##STR30## in which R.sub.5 is hydrogen, unsubstituted alkyl or alkyl substituted by one or more halogen, C.sub.1 -C.sub.4 -alkoxy, phenyl, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, mono- or di-C.sub.1 -C.sub.4 alkylated amino or --SO.sub.3 M groups or unsubstituted aryl or aryl substituted by one or more C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, C.sub.2 -C.sub.5 -alkanoylamino, nitro, sulpho or di-C.sub.1 -C.sub.4 alkylated amino groups or --NR.sub.7 R.sub.8 in which R.sub.7 and R.sub.8, independently, are hydrogen, unsubstituted alkyl or alkyl substituted by one or more halogen, C.sub.1 -C.sub.4 -alkoxy, phenyl, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, mono- or di-C.sub.1 -C.sub.4 alkylated amino or --SO.sub.3 M groups or unsubstituted aryl or aryl substituted by one or more C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, C.sub.2 -C.sub.5 -alkanoylamino, nitro, sulpho or di-C.sub.1 -C.sub.4 alkylated amino groups, or R.sub.7 and R.sub.8, together with the nitrogen atom to which they are attached, form a morpholine or piperidine ring;
##STR31## in which R.sub.5 is hydrogen, unsubstituted alkyl or alkyl substituted by one or more halogen, C.sub.1 -C.sub.4 -alkoxy, phenyl, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, mono- or di-C.sub.1 -C.sub.4 alkylated amino or --SO.sub.3 M groups or unsubstituted aryl or aryl substituted by one or more C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, C.sub.2 -C.sub.5 -alkan-oylamino, nitro, sulpho or di-C.sub.1 -C.sub.4 alkylated amino groups, provided that R.sub.5 is not carboxymethyl or hydroxymethyl;
R.sub.2 is hydrogen, unsubstituted alkyl or alkyl substituted by one or more halogen, C.sub.1 -C.sub.4 -alkoxy, phenyl, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, mono- or di-C.sub.1 -C.sub.4 alkylated amino or --SO.sub.3 M groups or unsubstituted aryl or aryl substituted by one or more C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, C.sub.2 -C.sub.5 -alkanoylamino, nitro, sulpho or di-C.sub.1 -C.sub.4 alkylated amino groups, ##STR32## --OH,--NH.sub.2,--N(CH.sub.2 CH.sub.2 OH).sub.2, --NCH.sub.2 CH(OH)CH.sub.3 !.sub.2,--NH--R.sub.4,--N(R.sub.4).sub.2 or --OR.sub.4, in which R.sub.4 has its previous significance;
and n.sub.1 and n.sub.2, independently, are 0 or 1, provided that the compounds in which n.sub.1 and n.sub.2 are each 1, R.sub.1 is ##STR33## in which R.sub.3 or R.sub.4 is unsubstituted alkyl and R.sub.2 is --OR.sub.4 in which R.sub.4 is naphthyl are excluded.

4 more elements