Ciba-geigy Corporation

Christian Luthi

Kurt Weber

Hans R Meyer

Eduard Troxler

Geza Kormany

Max Dunnenberger

Hans Rudolf Biland

Bruno Kagi

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.

Distyrylbiphenyls

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 Y' 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 -alkylene, 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, or 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 distyrylbiphenyldiamine 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.

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.crclbar. may not be a phosphite or phosphonate anion, and Y and Y' independently of one another are C.sub.1--20 --alkylene, 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, or 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.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 distyrylbiphenyldiamine 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.

The invention relates to cationic fluorescent whitening agents of the formula ##STR1## wherein A is the radical of a fluorescent whitening agent, Q is the direct bond or a bridge member, R.sub.1 to R.sub.5 are specific substituents and n is 1 or 2. A process for the manufacture of these compounds and a method of whitening organic material which comprises their use are also disclosed.

Cationic fluorescent whitening agents

Benzodifuranes of the formula ##STR1## wherein R represents hydrogen, alkyl or halogen, each of R.sub.1, R.sub.2 and R.sub.3 represents hydrogen or different non-chromophoric substituents, with the proviso that at least one of the symbols R, R.sub.1, R.sub.2 or R.sub.3 does not represent hydrogen, processes for their production and the use thereof for whitening organic material of high molecular weight, especially polyester, polyvinyl chloride or polystyrene.

Certain bis(phenyl)-benzodifurans

(Pyrazolinylphenylsulfonyl)-piperazines of the formula ##STR1## wherein R.sub.1 is unsubstituted or substituted alkyl, aralkyl or alkenyl, R.sub.2 is unsubstituted or substituted alkyl, aryl or aralkyl R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are certain substituents and Y is an anion, their preparation as well as their use as optical brighteners are disclosed.

Quaternized 1-(pyrazolinylphenylsulphonyl)-piperazines

The present invention relates to the optically brightening of organic fibrous materials with compositions containing a mixture of 1.2-bis-[5-methyl-benzimidazol-(2)-yl]-ethylene and 2.5-bis-[benzoxazol-(2)-yl]-thiophene. The mixture of said brighteners show surprising synergistic effects.

Optically brightening with a synergistic mixture

New diarylvinyl-dihydrophenanthrene compounds of the formula ##STR1## wherein R.sub.1, R.sub.1 ', R.sub.2, R.sub.2 ', R.sub.3 and R.sub.3 ' are identical or different and represent hydrogen, alkyl with 1 to 12 carbon atoms, aralkyl with 1 to 4 carbon atoms in the alkyl part, alkoxy with 1 to 18 carbon atoms, phenyl-alkoxy with 1 to 4 carbon atoms in the alkoxy part, alkenyloxy with 3 to 4 carbon atoms, halogen, nitrile, a sulphonic acid group or its salts or functional derivatives, a carboxyalkoxy or carboxyl group or their salts or functional derivatives, or a sulphone group. These compounds are particularly useful as optical brighteners.

Diarylvinyl-dihydrophenanthrene compounds

The invention concerns specific new oxalic acid diarylamides which are characterized by an asymmetrical substitution with regard to the central oxalic amide moiety of the formula

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Basel, Switzerland

Christian Luthi