Ciba-geigy Corporation

Gerd Holzle

Gerhard Reinert

Rudolf Polony

Andre Pugin

Claude Eckhardt

Mirella Miotto

Gregor Graf

Rodolphe Vonderwahl

Rainer Begrich

Sandor Gati

Novel azaphthalocyanines are described which are of the formula ##STR1## in which Me is Al(III), Zn(II), Ge(IV) or Sn(IV), E is an anionic group, Z is a cation, Y is a halogen, n is any desired number from 1 to 3 and p is any desired number from 0 to 2, the sum n+p being at most 8 and A, B, C and D independently of one another completing a benzene ring or a ring of the formula ##STR2## at least one of the rings completed by A, B, C or D being one of the said heterocyclic rings. The novel compounds can be used as photoactivators, in particular for bleaching textiles and for controlling microorganisms in or on organic or inorganic substrates. Bleaching, washing and steeping agents and antimicrobially active agents are also described which contain the novel azaphthalocyanine compounds. The azaphthalocyanine pigments which arise as intermediates and which do not carry groups EZ imparting solubility in water, their preparation and their use as photosensitizers in non-aqueous or heterogeneous systems are likewise described.

Water-soluble azaphthalocyanines and their use as photoactivators in

Novel phthalocyanine compounds are described, which have the formula ##STR1## in which MePc is the Si(IV)-, P(V)-, Ti(IV)-, Ge(IV)-, Cr(IV)-, Ga(III)-, Zr(IV)-, In(III)-, Sn(IV)- or Hf(IV)- phthalocyanine or -naphthalocyanine ring system, A is an anionic, nonionic or cationic group which imparts solubility in water, Z is the counter-ion to A, if the latter is an ionic group, and is 0 if A is a nonionic group, n is any desired number from 1 to 8, Y is a neutral substituent which does not impart solubility in water and p is any desired number from 0 to 6, it being possible for the groups AZ and Y present in the molecule to be identical or different in either case, and the sum of n+p being not more than 8 and MePc not being the Sn(IV)-phthalocyanine or Sn(IV)-naphthalocyanine ring system if p is 0 and if the only groups imparting water-solubility in the molecule are sulfo groups. The novel compounds can be used as photoactivators, particularly for bleaching textiles and for controlling microorganisms in or on organic or inorganic substrates. Bleaching, washing and steeping agents and agents having antimicrobial activity, which contain the novel phthalocyanine compounds, are also described.

Water-soluble phthalocyanine compounds

The invention relates to novel zinc and aluminium phthalocyanine compounds of the formula ##STR1## wherein MePc is the zinc or aluminium phthalocyanine ring system, M is hydrogen or a salt-forming cation, R.sub.1 is hydrogen or a group of the formula --NH--CN or NH--SO.sub.2 R.sub.3 or the salts thereof, wherein R.sub.3 is alkyl, aryl or a heterocyclic ring system, R.sub.2 is a neutral, non-solubilizing substituent, n is 1 to 4 and each of m and q is 0 to 3 and p is 0 to 4. These compounds are prepared by starting from the corresponding sulfohalides. The novel compounds are used as photoactivators, especially for bleaching and removing stains from textiles and for combating microorganisms in or on organic or inorganic substrates. The invention also relates to bleaching, detergent and soaking and microbicidal compositions which contain the novel phthalocyanine compounds.

Water-soluble zinc and aluminium phthalocyanines and use thereof as

The invention discloses fabric conditioning compositions which contain, as bleach photoactivator, an aluminium or zinc phthalocyanine which is substituted by cationic water-solubilizing groups, and also cationic fabric conditioners such as cationic surfactants, softeners, antistatic agents, fluorescent whitening agents and/or microbicides. The invention also provides a method of washing, rinsing and bleaching fabrics utilizing the compositions of the invention, as well as novel aluminium and zinc phthalocyanines which contain quaternary ammonium groups and ternary sulfonium groups as substituents.

Zinc and aluminum phthalocyanines

A process for combating micro-organisms in or on organic or inorganic substrates and for protecting the said substrates against attack by micro-organisms, which comprises treating the substrates with a water-soluble phthalocyanine derivative, in the presence of oxygen and water and while irradiating with light in the infra-red and/or visible range, antimicrobical agents containing water-soluble phthalocyanine compounds as well as new phthalocyanine compounds are described.

Phthalocyanine compounds and anti-microbial use

The invention relates to novel zinc and aluminium phthalocyanine compounds of the formula ##STR1## wherein MePc is the zinc or aluminium phthalocyanine ring system, M is hydrogen or a salt-forming cation, P.sub.1 is hydrogen or a group of the formula --NH--CN or NH--SO.sub.2 R.sub.3 or the salts thereof, wherein R.sub.3 is alkyl, aryl or a heterocyclic ring system, R.sub.2 is a neutral, non-solubilizing substituent, n is 1 to 4 and each of m and q is 0 to 3 and p is 0 to 4. These compounds are prepared by starting from the corresponding sulfohalides. The novel compounds are used as photoactivators, especially for bleaching and removing stains from textiles and for combating microorganisms in or on organic or inorganic substrates. The invention also relates to bleaching, detergent and soaking and microbicidal compositions which contain the novel phthalocyanine compounds.

Water-soluble zinc and aluminium phthalocyanines

A process is proposed for bleaching textiles or removing stains from textiles and for combating micro-organisms in or on organic or inorganic substrates, or for protecting the latter against attack by micro-organisms, by treating the textiles or the substrates to be freed of or protected from micro-organisms with a water-soluble zinc phthalocyanine or aluminium phthalocyanine, in the presence of water and under irradiation with light, in which process a sulfonated zinc phthalocyanine or aluminium phthalocyanine which is further substituted by neutral groups which do not confer solubility in water, for example by halogen atoms or pseudo-halogens, or a mixture of these phthalocyanine compounds, is used as the water-soluble zinc phthalocyanine or aluminium phthalocyanine. Bleaching, washing and soaking agents or agents having an antimicrobial action, for carrying out the process, are also proposed, which, in addition to the active ingredient, contain, if appropriate, inorganic salts, water and also, in the case of washing agents, customary washing-agent constituents. Novel sulfonated zinc phthalocyanine and aluminium phthalocyanine compounds and their preparation are furthermore described.

Process for bleaching textiles and for combating microorganisms with

Azo dyes of the formula ##STR1## wherein D is benzene, naphthalene, benzoylaminobenzene, azobenzene or stilbene, which is unsubstituted or substituted by alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, phenoxy, alkanoylamino of 1 to 6 carbon atoms, benzoylamino, amino, alkylamino of 1 to 4 carbon atoms, phenylamino, alkoxycarbonyl of 1 to 5 carbon atoms, alkylcarbonyl of 1 to 5 carbon atoms, nitro, cyano, acetyl, carbamoyl, ureido, hydroxy, carboxy, halogen or sulfo, and which contains a dihalo-s-triazinylamino or a monohalo-s-triazinylamino radical substituted by an alkyl, aryl, alkylthio, arylthio, hydroxy, alkoxy, aryloxy, -NH.sub.2, alkylamino, arylamino or heterocyclic amino group, wherein the halo-s-triazinylamino radical is bonded directly or via methylene to a ring carbon of D, and the amino group, by which the halo-s-trazinyl radical is bonded to a carbon atom in D is optionally substituted at the nitrogen atom by C.sub.1-4 -alkyl or -sulfoalkyl, R is hydrogen or alkyl of 1 to 4 carbon atoms, and R.sub.1 and R.sub.2, independently of one another, have the same meaning as those substituents referred to above of monohalo-s-triazinyl radicals in D; or a heavy metal complex thereof, are especially suitable for dyeing cotton fabric according to the exhaustion dyeing method and produce dyeings which have good fastness properties.

Fibre-reactive azo dyestuffs containing a halotriazinyl radical and a

A process is proposed for bleaching textiles or removing stains from textiles and for combating micro-organisms in or on organic or inorganic substrates, or for protecting the latter against attack by micro-organisms, by treating the textiles or the substrates to be freed of or protected from micro-organisms with a water-soluble zinc phthalocyanine or aluminium phthalocyanine, in the presence of water and under irradiation with light, in which process a sulfonated zinc phthalocyanine or aluminium phthalocyanine which is further substituted by neutral groups which do not confer solubility in water, for example by halogen atoms or pseudo-halogens, or a mixture of these phthalocyanine compounds, is used as the water-soluble zinc phthalocyanine or aluminium phthalocyanine. Bleaching, washing and soaking agents or agents having an antimicrobial action, for carrying out the process, are also proposed, which, in addition to the active ingredient, contain, if appropriate, inorganic salts, water and also, in the case of washing agents, customary washing agent constituents. Novel sulfonated zinc phthalocyanine and aluminium phthalocyanine compounds and their preparation are furthermore described.

Process for bleaching textiles and for combating micro-organisms with

Fabric conditioning compositions containing phthalocyanine substituted

The invention provides reactive dyes of the formula ##STR1## wherein Pc is the radical of a copper or nickel phthalocyanine, X is a substituted or unsubstituted amino group, A is an alkylene or arylene radical, Y is a removable or non-removeable substituent, W is sulfo or carboxyl, and Z is a reactive radical, and a, b and c are whole or fractional numbers, with the proviso that each of a and c is at least 1, b is a value between 0 and 2 and the sum of a+b+c must be 4.

Reactive dyes, processes for their manufacture and their use

Process for combating micro-organisms, and novel phthalocyanine compounds

A process for bleaching textiles which comprises treating stained textiles in an aqueous bath containing at least one water-soluble aluminium phthalocyanine, under irradiation with light and in the presence of oxygen, while either irradiating the bleaching bath direct or subsequently irradiating the moist textiles outside the bath, as well as water-soluble aluminium phthalocyanines containing detergent compositions are described.

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Liestal, Switzerland

Gerd Holzle