Ciba-geigy Corporation

Ciba Specialty Chemicals Corporation

Rudolf Zink

Dieter Reinehr

Ian J Fletcher

Peter Loew

Helmut Luther

Stefan Koller

Werner H&ouml;lzl

Armando Di Teodoro

Rox Phaff

Hanspeter Sauter

Klaus Huber

Peter Rohringer

Kurt Burdeska

Hansrudolf Schwander

Bernd Herzog

Peter Mockli

Urs Burckhardt

Rosalinde Braun

Uwe Gronde

The present invention provides compounds having the formula (1) in which each of the radicals R , R , R and R , independently, represent hydrogen, hydroxy, halogen, C -C -alkyl, C -C -alkoxy, CN or COOR , in which R is C -C -alkyl and Z represents a heterocyclic residue selected from the 2H-benzo&lsqb;1,2-d&rsqb;triazol-2-yl, 2H-naphtho&lsqb;1,2-d&rsqb;triazol-2-yl, benzimidazol-2-yl, benzoxazol-2-yl and benzofuran-2-yl moieties, optionally substituted by C -C -alkyl, C -C -alkoxy, halogen or NHCOC -C -alkyl, a process for their preparation, new intermediate benzoxazinones useful for their preparation and use of the compounds of formula (1) as UV-absorbers which have improved absorption spectrum characteristics, superior resistance to exposure to UV light and excellent thermal stability, relative to known triphenyltriazine compounds.

Heteroaryl substituted hydroxyphenyltriazine uv-absorbers

Indolin derivaties as sun protection agents

There is described a process for the preparation of halogenated hydroxydiphenyl compounds of formula (1) by acylation of a halogenated benzene compound (first stage), etherification of the acylated compound with a halogenated phenol compound, which is not further substituted in the ortho-position (second stage), oxidation of the etherified compound (third stage) and hydrolysis of the oxidized compound in a fourth stage, wherein the reaction of the second stage is carried out in the presence of K CO and any desired copper catalyst, where K CO is used in a concentration of from 0.5 to 30 mol, based on the phenol compound employed of formula (6), according to the reaction scheme (I) in which R and R independently of one another are F, Cl or Br; R and R independently of one another are hydrogen; or C -C alkyl; m is 1 to 3; and n is 1 or 2. The compounds of formula (1) are used for protecting organic materials and articles from microorganisms.

Process for the preparation of halogenated hydroxydiphenyl compounds

A description is given of a three-step process for the preparation of 4,4&prime;-dihalogen-o-hydroxydiphenyl compounds of formula (1) which comprises: a) hologenating an alkoxyphenol of formula (6) (&equals;a ), reacting the resulting halogenated phenol compound of formula (5) with p-dihalobenzene of formula (4 ) in the presence of copper and/or copper salts to the diphenyl ether compound of formula (2) (&equals;a ) and subsequent ether fission to the diphenyl ether compound of formula (1) (&equals;a ); or b) reacting an alkoxyphenol of formula (6) with the halophenol of formula (4 ) to the compound of formula (3) (&equals;b ), then halogenating this compound (&equals;b ) and subsequent ether fission of the resulting compound of formula (2) to the diphenyl ether compound of formula (1) (&equals;b ). The compounds of formula (1) are used for protecting organic materials and objects against microorganisms.

Process for the preparation of 4,4&prime;-dihalogen-o-hydroxydiphenyl compounds

Biphenyl compounds substituted by camphor or hydantoin derivatives as sunscreen compositions

Indolin derivatives as sun protection agents

A process for the preparation of halohydroxydiphenyl compounds useful for protecting organic materials and articles from microorganisms, of the formula

The invention is related to a composition containing benzotriazole derivatives of formula (I) and the method of treating skin damages due to harmful UV radiation using this claimed composition.

Use of selected benzotriazole derivatives for protecting human and animal skin and hair from the harmful effects of UV radiation

The invention describes a color former mixture comprising

Color former mixture

The invention describes a colour former mixture comprising

The invention relates to bislactone color formers having improved fastness to sublimation and migration stability, to their preparation, to pressure-sensitive and heat-sensitive recording materials containing said compounds and to their preparation. The novel bislactones have the formula (1) as defined in claim 1.

Bislactones

The invention relates to fluoran colour formers having improved fastness to sublimation and migration stability, to their preparation, to pressure-sensitive and heat-sensitive recording materials containing said compounds and to their preparation. The fluorans have the formula (I) as defined in claim 1.

Fluoran color formers

A pressure-sensitive or heat-sensitive recording material essentially comprising in its color reactant system

Pressure-sensitive or heat-sensitive recording material

A heat-sensitive recording material which contains

Heat-sensitive recording material

Bisphthalide lactones of formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each independently of one another hydrogen, alkyl of at most 12 carbon atoms which is unsubstituted or substituted by halogen, hydroxy, cyano, tetrahydrofuryl or lower alkoxy; or are acyl of 1 to 12 carbon atoms, cycloalkyl of 5 to 10 carbon atoms or unsubstituted aralkyl or aryl, or aralkyl or aryl each substituted by halogen, cyano, nitro, trifluormethyl, lower alkyl, lower alkoxy, lower alkoxycarbonyl, --NX'X'-- or 4--NX'X--'phenylamino, wherein X' and X' are each independently of the other hydrogen, lower alkyl, cyclohexyl, benzyl or phenyl, or the pairs of substituents --NR.sub.1 R.sub.2 and --NR.sub.3 R.sub.4 are each a 5- or 6-membered, preferably saturated, heterocyclic radical, V.sub.1 and V.sub.2 are hydrogen, halogen, lower alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -C.sub.12 -acyloxy, benzyl, phenyl, benzyloxy, phenyloxy, or benzyl or benzyloxy, each substituted by halogen, cyano, lower alkyl or lower alkoxy, or are the group --NT.sub.1 T.sub.2, in which T.sub.1 and T.sub.2 are each independently of the other hydrogen, lower alkyl, C.sub.5 -C.sub.10 cycloalkyl, unsubstituted benzyl or benzyl which is substituted by halogen, cyano, lower alkyl or lower alkoxy, or are acyl of 1 to 8 carbon atoms, and T.sub.1 is also unsubstituted phenyl or phenyl which is substituted by halogen, cyano, lower alkyl or lower alkoxy, and the rings A.sub.1 and A.sub.2 are each independently of the other an aromatic or heterocyclic radical of 6 ring atoms which may contain an aromatic fused ring, which rings A.sub.1 and A.sub.2 as well as the fused rings may be substituted. These bisphthalide lactones can be used as color forming components in pressure-sensitive or heat-sensitive recording materials and, when used in conjunction with a condensation component and an acid developer, form intense colored images.

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Therwil, Switzerland

Rudolf Zink