Ciba-geigy Corporation

Werner Stegmann

Reto Luisoli

Roland A Winter

David G Leppard

Paul Dubs

Roger Martin

Robert E Detlefsen

Samuel Evans

Siegfried Rosenberger

Hans-Rudolf Meier

Hans R Meier

Peter Hofmann

Eduard Troxler

Robert E Detiefsen

Compounds of formula Ia ##STR1## in which R.sub.1 is hydrogen, R.sub.2 is methyl, tert-butyl or cyclohexyl, and R.sub.7 and R.sub.8 independently of one another are C.sub.1 -C.sub.18 alkyl, phenyl or C.sub.7 -C.sub.18 alkylphenyl are novel compounds having utility as stabilizers.

Cyclohexyl substituted hydroxybenyzlphosphonates

Liquid substituted 2H-benzotriazole mixtures are prepared by alkylation with concomitant dealkylation, fragmentation and realkylation of 2-(2-hydroxy-5-alkylphenyl)-2H-benzotriazoles or of 2-(2-hydroxy-3,5-dialkylphenyl)-2H-benzotriazoles with straight or branched alkenes of 8 to 30 carbon atoms in the presence of an acid catalyst at 100.degree.-200.degree. C. The liquid mixtures exhibit outstanding efficacy in protecting organic substrates from light induced deterioration as well as good resistance to loss by volatilization or exudation during the processing of stabilized compositions at elevated temperatures.

Liquid substituted 2H-benzotriazole mixtures, stabilized compositions

Compounds of formula ##STR1## wherein R.sub.1 is hydrogen alkyl, alkoxy, phenyl, phenylaklyl or halogen, and R.sub.2 is alkyl phenyl, phenylaklyl or cycloalkyl, are prepared by reacting a compound of formula ##STR2## with a compound of formula ##STR3## wherein R.sub.3 and R.sub.4 are alkyl, and formaldehyde, in a one-pot process in the absence of a solvent.

Process for the preparation of symmetrical

A process for the preparation of compounds of the general formula I ##STR1## in which R.sub.1 is hydrogen or methyl, R.sub.2 and R.sub.3 independently of one another are C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.8 cycloalkyl, phenyl, C.sub.7 -C.sub.9 phenylalkyl or halogen, R.sub.2 is additionally hydrogen and R.sub.7 and R.sub.8 independently of one another are C.sub.1 -C.sub.18 alkyl, phenyl or C.sub.7 -C.sub.18 alkylphenyl, which comprises reacting a phenol of the formula II ##STR2## in which R.sub.1 to R.sub.3 have the meaning described above, with formaldehyde or paraformaldehyde, an amine of the formula III

Process for the preparation of hydroxybenzylphosphonates

A process for the preparation of compounds of formula I ##STR1## by reacting a phenol with formaldehyde and a thiol of formula HS--C.sub.n H.sub.2n --COO--R.sub.3 under excess pressure and in the presence of dimethylamine. The symbols R.sub.1 and R.sub.2 are independently alkyl, R.sub.3 is alkyl or alkyl interrupted by --O-- or --S--, and n is 1 or 2.

Process for the preparation of phenolic thiocarboxylic acid esters

Liquid substituted, 2H-benzotriazole mixtures are prepared by alkylation with concomitant dealkylation, fragmentation and realkylation of 2-(2-hydroxy-5-alkylphenyl)-2H-benzotriazoles or of 2-(2-hydroxy-3,5-dialkylphenyl)-2H-benzotriazoles with straight or branched alkenes of 8 to 30 carbon atoms in the presence of an acid catalyst at 100.degree.-200.degree. C. The liquid mixtures exhibit outstanding efficacy in protecting organic substrates from light induced deterioration as well as good resistance to loss by volatilization or exudation during the processing of stabilized compositions at elevated temperatures.

Stabilized compositions containing liquid substituted 2H-benzotriazole

Bis-(amino-nitrophenyl)-methane can be produced in one stage with an approximately quantitative yield by condensing o-nitraniline and formaldehyde in water at a temperature of between 20.degree. and 40.degree. C. in the presence of sulfuric acid, and subsequently rearranging the formed methylene-bis-(o-nitraniline) by treatment of the reaction mixture at a temperature of between 90.degree. and 100.degree. C.

Single-stage process for producing bis-(amino-nitrophenyl)-methane

A process for the preparation of a mixture of 2-(2-hydroxyphenyl)benzotriazole which is liquid at room temperature by alkylating 2-(2-hydroxy-5-methylphenyl)benzotriazole with a C.sub.8 -C.sub.14 .alpha.-olefin in the melt at elevated temperature, in the presence of sulfonic acid as catalyst, comprising using not less than 0.5 mol of the acid catalyst and 1.5-3 mol of .alpha.-olefin per mol of 2-(2-hydroxy-5-methylphenyl)benzotriazole, carrying out the alkylation in the temperature range from 165.degree. to 190.degree. C., separating the crude product phase upper phase) from the sulfonic acid phase, and working up said crude product phase by distillation by means of a thin-film evaporator, a thin-film evaporator fitted with a distillation column, or a short path distillation apparatus.

Process for the preparation of liquid mixtures of alkylated

There is disclosed a process for the preparation of compounds of formula I or II ##STR1## from phenols by reaction with formaldehyde and mercaptans in the presence of mono-, di- or trimethylamine or mono- or diethylamine. The symbols R.sub.1 is alkyl, hydroxy or alkoxycarbonyl substituted alkyl; alkyl; aryl, cycloalkyl or aralkyl, R.sub.2 is hydrogen, alkyl, alkenyl or halogen, R.sub.3 and R.sub.4 are independently alkyl, allyl, cycloalkyl, phenyl, benzyl, halogen or --CH.sub.2 --S--R.sub.1, Z.sub.1 is --S-- or alkylene, and Z.sub.2 is hydrogen, alkyl or --CH.sub.2 --S--R.sub.1. The mercaptomethylphenols are valuable antioxidants for plastics, elastomers, mineral oils and synthetic lubricants.

Process for the preparation of mercaptomethylphenols

Compounds of the formula I ##STR1## R.sup.4 is C.sub.5 -C.sub.7 -cycloalkyl which can be substituted by C.sub.1 -C.sub.4 -alkyl, and R.sup.5 to R.sup.9 are independently of one another C.sub.1 -C.sub.18 alkyl, unsubstituted or C.sub.1 -C.sub.4 -alkyl-substituted C.sub.5 -C.sub.7 -cycloalkyl, phenyl, benzyl or allyl, are suitable for stabilizing organic material against thermal, oxidative and/or actinic degradation.

Isocyanuric acid derivatives

The invention relates to a novel process for producing compounds of the formula I ##STR1## in which R.sup.1 is for example phenyl, and R.sup.2 and R.sup.3 are for example cyclohexyl. With application of the phase-transfer catalysis method, a corresponding compound of the formula II ##STR2## is reacted, in the presence of water, with hydroxide ions, especially with alkali metal hydroxide or alkaline-earth metal hydroxide.

Process for producing 1-hydroxy ketones

Compounds of the formula I ##STR1## wherein R.sup.1 and R.sup.2 independently of one another are each tert-butyl, R.sup.3 is C.sub.1 -C.sub.20 -alkyl, or C.sub.2 -C.sub.20 -alkyl interrupted by --O-- or --S--, and n is the number 1 or 2, can be obtained, with a very high degree of yield and purity, by reaction of a phenol of the formula II ##STR2## with formaldehyde and a mercaptan of the formula III

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Werner Stegmann