Ciba-geigy Corporation

Ciba-geigy Ag

Other

Ciba-ceigy Corporation

Ciga-geiby Corporation

Hans R Meyer

Kurt Weber

Dieter Reinehr

Leonardo Guglielmetti

Claude Eckhardt

Christian Luthi

Peter Liechti

Adolf Emil Siegrist

Max Siegrist

Kurt Burdeska

Jurgen Kaschig

Klaus Artz

Heinz Hefti

Reinhard Zweidler

Max Morf

Novel benzofuranylbiphenyl compounds of the formula ##STR1## which are unsubstituted or polysubstituted by radicals R=hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, phenoxy and benzyloxy and in which M is hydrogen and/or one equivalent of a non-chromophoric cation and n is the number zero, 1 or 2 and m is the number zero or 1, subject to the condition that n and m are not both zero, and the preparation and use thereof as fluorescent brighteners, for example for textiles and paper. The novel benzofuranylbiphenyl compounds are distinguished by their very good stability associated with excellent whitening properties.

Sulfonation of benzofuranylbiphenyls

Novel dibenzofuranylbiphenyl compounds of the formula (I) ##STR1## which are unsubstituted or are monosubstituted or polysubstituted by radicals R=hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, phenoxy and benzyloxy and in which R.sub.3 is C.sub.1 -C.sub.4 alkyl, halogen or phenyl and M is hydrogen and/or one equivalent of a non-chromophoric cation and the preparation and use thereof for fluorescent whitening are described.

Dibenzofuranylbiphenyls

Detergents containing certain sulfonated dibenzofuranylbiphenyls

The invention relates to pyrazoline compounds of formula ##STR1## wherein R.sub.1 is hydrogen or methyl, R.sub.2 and R.sub.3 are each independently of the other methyl, ethyl or hydroxyethyl, R.sub.4 is hydrogen or chlorine, R.sub.5 and R.sub.6 are each independently of the other hydrogen or methyl, R.sub.7 is hydrogen, methyl or phenyl, n is 0 or 1, with the proviso that, if n is 0 and R.sub.4 to R.sub.7 are hydrogen, R.sub.2 is methyl and R.sub.3 is hydroxyethyl, and X.sup..crclbar. is a C.sub.1 -C.sub.3 alkanoate, C.sub.1 -C.sub.4 alkanephosphonate, C.sub.1 -C.sub.4 alkanesulfonate, phosphite, sulfamate or glycolate anion and, if R.sub.1 is methyl, X.sup..crclbar. is also a methosulfate, chloride or bromide ion, to the preparation of said compounds, to the use thereof as fluorescent whitening agents, and to novel hydrazine intermediates of formula ##STR2## wherein R.sub.2 and R.sub.3 are methyl, ethyl or hydroxyethyl, and the acetone hydrazones and salts thereof.

Pyrazoline compounds

Novel 1,4-distyrylbenzene compounds of the formula ##STR1## and mixtures thereof with compounds of the formulae ##STR2## and/or ##STR3## in which R.sub.1 is C.sub.1 -C.sub.4 -alkyl or phenyl, R.sub.2 is cyano, COOC.sub.1 -C.sub.4 -alkyl or chlorine and R.sub.3 is hydrogen or chlorine, agents for the fluorescent brightening of polyester fibers and a process for the preparation of the compounds of the formula 1 or mixtures thereof with compounds of the formulae 2 and/or 3 and also novel aldehydes which can be isolated as intermediates.

1,4-distyrylbenzene compounds and mixtures thereof with other

Mixtures of fluorescent whitening agents consisting of 51 to 99% by weight of 1-(4-cyanostyryl)-4-(3'-styryl)benzene, 49 to 1% by weight of 1-(4-cyanostyryl)-4-(2'-cyanostyryl)benzene and 0.5 to 5% by weight of 1,4-bis(cyanostyryl)benzene, a process for the preparation of said mixtures by condensing terephthalaldehyde with a 4-dialkylphosphonomethylbenzonitrile to 4-cyano-4'-formylstilbene, which is further condensed, either direct or after isolation, with a 3- and 2-dialkylphosphonomethylbenzonitrile, the use of these mixtures for whitening polyester fibres, and compositions containing said mixtures for whitening polyester fibres.

Mixtures of fluorescent whitening agents

Detergents which, in addition to inorganic and/or organic peracids, contain specific stilbene compounds as fluorescent whitening agents. These detergents are stable for several months and already show the customary cleaning properties at washing temperatures of 20.degree.-60.degree. C.

Stable bleaching detergents containing stilbene fluorescent whitening

New pyrazoline compounds of the formula ##STR1## in which X is 1,4-phenylene, ##STR2## if n is 1 or if R.sub.7 or R.sub.8 contains an SO.sub.3 M Radical, also a methylene or --CH.sub.2 CH(OH)--CH.sub.2 O-- group or an unbranched C.sub.1 -C.sub.4 alkyleneoxy group, a direct bond or oxygen, R.sub.1, R.sub.2 and R.sub.3 independently of one another are hydrogen, chlorine or C.sub.1 -C.sub.4 alkyl, R.sub.7 is C.sub.1 -C.sub.4 alkyl, chlorophenyl, hydrogen, phenyl or --C.sub.6 H.sub.4 --SO.sub.3 M, R.sub.8 is H, C.sub.1 -C.sub.4 alkyl, --CH.sub.2 SO.sub.3 M, carboxyl, C.sub.2 -C.sub.5 carboalkoxy, carbamoyl or carboxymethyl, R.sub.9 is H, chlorine or C.sub.1 -C.sub.4 alkyl, Ar is a phenyl radical which is unsubstituted or substituted by non-chromophores or, if X is a direct bond, also a naphthalene radical, M is hydrogen or one equivalent of a non-chromophoric cation and m and n are the number nought or 1, which can be used as fluroescent brighteners for synthetic and natural fibres, especially for polyamide. A process for the preparation of these compounds, their use as fluorescent brighteners and agents containing the compounds for the fluorescent brightening of fibres and lacquers composed of acetylcellulose, wool and especially polyamide, and also novel hydrazines as an intermediate in the preparation of the compounds.

Mixtures of fluorescent whitening agents consisting of 51 to 99% by weight of a symmetrically or unsymmetrically substituted first 1,4-bis(cyanostyryl)benzene and 49 to 1% by weight of an unsymmetrically substituted second 1,4-bis(cyanostyryl)benzene that differs from the first, a process for the preparation of said mixtures by condensing terephthalaldehyde with a di(C.sub.1 -C.sub.4)alkylphosphonomethylbenzonitrile to cyano-4-formylstilbene, which is further condensed, either direct or after isolation, with at least one other di(C.sub.1 -C.sub.4)alkylphosphonomethylbenzonitrile, the use of these mixtures for whitening polyester fibres, and compositions containing said mixtures for whitening polyester fibres.

Mixtures of fluorescent whitening agents consisting of 51 to 98.5% by weight of 1-(4-cyanostyryl)-4-(3'-styryl)benzene, 48.5 to 1% by weight of 1-(4-cyanostyryl)-4-(2'-cyanostyryl)benzene and 0.5 to 5% by weight of 1,4-bis(cyanostyryl)benzene, a process for the preparation of said mixtures by condensing terephthalaldehyde with a 4-dialkylphosphonomethylbenzonitrile to 4-cyano-4'-formylstilbene, which is further condensed, either direct or after isolation, with a 3- and 2-dialkylphosphonomethylbenzonitrile, the use of these mixtures for whitening polyester fibers, and compositions containing said mixtures for whitening polyester fibers.

Pyrazoline compounds and method of whitening

Mixtures of fluorescent whitening agents consisting of 51 to 99% by weight of a symmetrically or unsymmetrically substituted first 1,4-bis(cyanostyryl)benzene and 49 to 1% by weight of an unsymmetrically substituted second 1,4-bis(cyanostyryl)benzene that differs from the first, a process for the preparation of said mixtures by condensing terephthalaldehyde with a di(C.sub.1 -C.sub.4) alkylphosphonomethylbenzonitrile to cyano-4-formylstilbene, which is further condensed, either direct or after isolation, with at least one other di(C.sub.1 -C.sub.4)alkylphosphonomethylbenzonitrile, the use of these mixtures for whitening polyester fibres, and compositions containing said mixtures for whitening polyester fibres.

Stilbene derivatives of the formula ##STR1## wherein X is chlorine or bromine, R.sub.1 is hydrogen, carboxyl, cyano, C.sub.1 -C.sub.6 -alkyl or a non-chromophorically esterified carboxyl group, and R.sub.2 and R.sub.3 independently of one another are each hydrogen, unsubstituted or non-chromophorically substituted C.sub.1 -C.sub.6 -alkyl or C.sub.3 -C.sub.4 -alkenyl, or a non-chromophoric substituent of the 2nd order. They are valuable intermediates for producing optical brighteners of the 4,4'-disubstituted stilbene series.

Stilbene derivatives

Novel 4-heterocyclylvinyl-4'-styryl-biphenyls of the formula ##STR1## are described, i which A is an isoxazolyl, oxadiazolyl, pyrimidinyl or triazinyl radical which is unsubstituted or substituted by a non-chromophoric substituent, R.sub.1 is hydrogen or a non-chromophoric substituent and R.sub.2 is hydrogen, halogen, or alkyl; processes for the preparation of these compounds are also described. The novel 4-heterocyclylvinyl-4'-styryl-biphenyls can be used as fluorescent brighteners for high-molecular organic materials, in particular materials of polyamide and polyester, especially for polyester textiles.

4-Heterocyclylvinyl-4-'styryl-biphenyls

The distyrylbiphenyls of the formula ##STR1## in which X and X' independently of one another are a direct bond, oxygen, sulfur, --O--C.sub.1-3 -alkylene-CON(R.sub.4)--CON(R.sub.4)--, --O--C.sub.1-3 alkylene-COO--, OCO or --COO--, with the proviso that if n+n'=O, X and X' may not be --CON(R.sub.4)-- or O--C.sub.1-3 -alkylene-CON(R.sub.4)--, and if n+n'=2 and X and X' are --CON(R.sub.4)-- or --COO--, A.sup..crclbar. may not be a phosphite or phosphonate anion, and Y and Y' independently of one another are C.sub.1-20 -alkyene, R.sub.1 and R.sub.1 ' independently of one another are unsubstituted or substituted C.sub.1-8 -alkyl or C.sub.3-4 -alkenyl, R.sub.1 together with R.sub.2, or R.sub.1 ' together with R.sub.2 ', is a heterocyclic ring, R.sub.2 and R.sub.2 ' independently of one another are unsubstituted or substituted C.sub.1-8 -alkyl or C.sub.3-4 -alkenyl, or R.sub.2 together with R.sub.1, or R.sub.2 ' together with R.sub.1 ', is a heterocyclic ring, or R.sub.1 and R.sub.2, or R.sub.1 ' and R.sub.2 ', together with R.sub.3 are a pyridine or picoline ring, R.sub.3 is hydrogen, unsubstituted or substituted C.sub.1-4 -alkyl or C.sub.3-4 -alkenyl or together with R.sub.1 and R.sub.2, or with R.sub.1 ' and R.sub.2 ', is a pyridine or picoline ring, R.sub.4 is hydrogen or unsubstituted or substituted C.sub.1-6 -alkyl, A.sup..crclbar. is a colorless anion and n and n' independently of one another are the number 0 or 1, and the benzene nuclei B and C can also be substituted by non-chromophoric substituents, can be prepared by reacting a correspondingly substituted benzaldehyde with a biphenyl phosphonate and then alkylating or protonating the distryrylbiphenyldiamine formed. The distyrylbiphenyls are fluorescent brightening agents for organic materials. They are particularly suitable for use as additives for textile and laundry after-treatment agents which contain cationic textile softeners.

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Binningen, Switzerland

Hans R Meyer