Ciba-geigy Corporation

Leonardo Guglielmetti

Hans R Meyer

Dieter Reinehr

Kurt Weber

Ian J Fletcher

Alain C Rochat

Process for preparing distyrylbiphenyl compounds by condensation of a substituted or unsubstituted 4,4'-bis(dialkoxyphosphonomethyl)biphenyl compound with a substituted or unsubstituted benzaldehyde in liquid ammonia as the solvent and in the presence of strong bases; and the use of these distyrylbiphenyl compounds as fluorescent whitening agents.

Process for preparing distyrylbiphenyl 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

A process is described for the preparation of 4,4'-dinitrostilbene-2,2'-disulfonic acid by oxidation of 4-nitrotoluene-2-sulfonic acid by using liquid, anhydrous ammonia, a liquid alkyl derivative of ammonia or a mixture of ammonia and/or the alkyl derivatives of ammonia with water as the solvent.

Process for the preparation of 4,4'-dinitrostilbene-2,2-disulfonic acid

A fluorescent brightener is proposed which consists of 51-99% of an unsymmetrically substituted compound of the formula ##STR1## in which R and R.sub.1 are identical or different and, if R and R.sub.1 are identical, R.sub.1 must occupy a position in the phenyl ring to which it is bonded which differs from the position occupied by R in its phenyl ring, and in which R and R.sub.1 independently of one another are CN or a corboxylic acid ester group, and 49-1% of a symmetrically substituted compound of the formula ##STR2## in which R is as defined above and the two R's are bonded to identical positions in their phenyl rings, as are also agents which contain these fluorescent brighteners and the use of these fluorescent brighteners for the fluorescent brightening of, in particular, textile materials, preferably made of polyester. The said fluorescent brighteners are prepared by reacting terephthaladehyde preferably with a correspondingly substituted benzylphosphonate and further reacting the resulting mixture of a correspondingly substituted 4-stilbene aldehyde and a symmetrical p-bis-styrylbenzene with a benzylphosphonate which differs from the benzylphosphonate first used.

Fluorescent brighteners consisting of bis-styrylbenzene compounds, a

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.

A fluorescent brightener is proposed which consists of 51-99% of an unsymmetrically substituted compound of the formula ##STR1## in which R and R.sub.1 are identical or different and, if R and R.sub.1 are identical, R.sub.1 must occupy a position in the phenyl ring to which it is bonded which differs from the position occupied by R in its phenyl ring, and in which R and R.sub.1 independently of one another are CN or a carboxylic acid ester group, and 49-1% of a symmetrically substituted compound of the formula ##STR2## in which R is as defined above and the two R's are bonded to identical positions in their phenyl rings, as are also agents which contain these fluorescent brighteners and the use of these fluorescent brighteners for the fluorescent brightening of, in particular, textile materials, preferably made of polymer. The said fluorescent brighteners are prepared by reacting terephthalaldehyde preferably with a correspondingly substituted benzylphosphonate and further reacting the resulting mixture of a correspondingly substituted 4-stilbene aldehyde and a symmetrical p-bis-styrylbenzene with a benzylphosphonate which differs from the benzylphosphonate first used.

Process for the preparation of bis-styrylbenzenes

A fluorescent brightener is proposed which consists of 51-99% of an unsymmetrically substituted compound of the formula ##STR1## in which R and R.sub.1 are identical or different and, if R and R.sub.1 are identical, R.sub.1 must occupy a position in the phenyl ring to which it is bonded which differs from the position occupied by R in its phenyl ring, and in which R and R.sub.1 independently of one another are CN or a carboxylic acid ester group, and 49-1% of a symmetrically substituted compound of the formula ##STR2## in which R as defined above and the two R's are bonded to identical positions in their phenyl rings, as are also agents which contain these fluorescent brighteners and the use of these fluorescent brighteners for the fluorescent brightening of, in particular, textile materials, preferably made of polyester. The said fluorescent brighteners are prepared by reacting terephthalaldehyde preferably with a correspondingly substituted benzylphosphonate and further reacting the resulting mixture of a correspondingly substitued 4-stilbene aldehyde and a symmetrical p-bis-styrylbenzene with a benzylphosphonate which differs from the benzylphosphonate first used.

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.

A process for the preparation of 4,4'-dinitrostilbene-2,2'-disulfonic acid and its salts, of the formula ##STR1## in which M is hydrogen or an alkali metal cation, by oxidation of 4-nitrotoluene-2-sulfonic acid in organic solvents, and also the reduction of the resulting acid or salt, without isolation, to give 4,4'-diamino- or (4-amino-4'-nitro)-stilbene-2,2'-disulfonic acid or salts thereof.

Process for the preparation of 4,4'-dinitrostilbene-2,2'-disulfonic acid

Novel amine oxide compounds of the formula ##STR1## in which m is the integer 1 or 2, A is a through-conjugated radical of a fluorescent brightener system, which radical contains unsubstituted or non-chromophorically substituted aromatic carbocyclic and/or heterocyclic rings, X is a direct bond between A and Y, an oxygen atom or sulfur atom or a group of the formula --SO.sub.2 --, --SO.sub.2 --O--, --COO--, --CON(R)-- or --SO.sub.2 N(R)--, in which R is hydrogen or unsubstituted or non-chromophorically substituted alkyl, Y is an unsubstituted or non-chromophorically substituted straight-chain or branched alkylene or alkyleneoxyalkylene group, and R.sub.1 and R.sub.2 independently of one another are cycloalkyl, unsubstituted or non-chromophorically substituted alkyl or phenyl, or R.sub.1 and R.sub.2, together with the nitrogen atom to which they are bonded, are a 5-membered or 6-membered saturated or unsaturated heterocyclic ring which can additionally contain one or two further hetero-atoms as ring members, and which can be substituted further, or, if X is a group of the formula --CON(R)-- or --SO.sub.2 N(R)-- and Y is ethylene or propylene, R and R.sub.1 together are an ethylene or methylene group, thereby forming a corresponding saturated heterocyclic ring containing 2 nitrogen atoms. The novel amine oxide compounds can be prepared, for example, by oxidizing the corresponding amino compounds with per-compounds. They can be used as fluorescent brighteners, especially for brightening cellulose in a washing liquor. The brighteners exhibit particularly advantageous properties when used in liquid detergents containing cationic textile softeners.

Amine oxide compounds

The invention relates to novel 4-styryl-4'-vinylbiphenyls of the formula ##STR1## wherein the benzene rings A, B and C can carry non-chromophoric substituents and R.sub.3 is a second order non-chromophoric substituent, and R.sub.4 is hydrogen or a non-chromophoric substituent which cannot be a second order substituent, and also a process for obtaining them. These novel compounds can be used as fluorescent whitening agents for treating organic material of high molecular weight, preferably textile material, most preferably polyester fibres. The invention also discloses novel intermediates of the formula ##STR2## wherein A, B and C are as defined above, which are formed during the production of the novel 4-styryl-4'-vinylbiphenyls, and also a process for obtaining them.

4-Styryl-4'-vinylbiphenyls, the production thereof and use thereof as

A process for the manufacture of 2,5-bis-(benzoxazolyl)-thiophenes of the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 represent hydrogen or certain non-chromophoric substituents and each of R.sub.4 and R.sub.5 independently represents a hydrogen atom or an alkyl group or together they represent a trimethylene or tetramethylene radical, by reacting a sulphide of the formula ##STR2## with a dicarbonyl compound of the formula ##STR3## or with a derivative thereof is described.

Process for the manufacture of 2,5-bis-(benzoxazolyl)-thiophene compounds

The present invention provides a new process for the manufacture of 1,4-disubstituted bicyclic or tricyclic compounds by reacting a 1,2-bis-cyanomethyl-benzene or 2,3-bis-cyanomethyl-naphthalene with glyoxal in the presence of a base and a solvent as well as new 1,4-disubstituted bicyclic compounds.

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Bottmingen, Switzerland

Leonardo Guglielmetti