Ciba-geigy Corporation

Rudolf Maul

Horst Zinke

Eberhard Otto

Eduard Troxler

Volker Schenk

Rita Pitteloud

Thomas Kainmuller

Peter Hofmann

Gerd Abeler

Siegfried Kintopf

Helmut Prestel

Hans Wolf Jung

Wolfgang Wehner

Joachim Lorenz

Hermann W Wehner

Heinz Steiner

Hans Stephan

Walter Wolf

Ulrich Kress

Heinz Issler

Wolfgang J Tritschler

Wilfried Kloss

Reinhard Knapp

Hans-Wolf Jung

Compounds of the formula I ##STR1## in which x is 1, 2 or 3, and, if x=1, R.sup.1 is C.sub.1 -C.sub.30 alkyl, C.sub.1 -C.sub.18 alkyl substituted by halogen, --COOR.sup.2, --CN, --NR.sup.3 R.sup.4 or by --CONR.sup.3 R.sup.4, C.sub.2 -C.sub.18 alkyl which is interrupted by --NR.sup.5 --, --O-- or --S--, C.sub.3 -C.sub.18 alkenyl, C.sub.5 -C.sub.12 cycloalkyl, phenyl-C.sub.1 -C.sub.4 alkyl, phenyl which is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl, halogen, phenyl-C.sub.1 -C.sub.4 alkyl and/or C.sub.1 -C.sub.4 alkoxy, or R.sub.1 is naphthyl, a radical of the formula ##STR2## R.sub.2, R.sub.3, R.sub.4 and R.sub.5, independently of one another, are hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.12 cycloalkyl or phenyl-C.sub.1 -C.sub.4 alkyl, R.sup.6 is hydrogen, methyl, allyl or benzyl, R.sup.7 is hydrogen or --OR.sup.9, R.sup.8 is hydrogen or methyl, R.sup.9 is hydrogen or C.sub.1 -C.sub.30 alkyl, R.sup.10 and R.sup.11, independently of one another, are hydrogen or C.sub.1 -C.sub.8 alkyl, and n is 3-6, with the proviso that R.sup.1 is not a phenyl radical which is substituted in both ortho-positions to the carbon atom bonded to the oxygen atom, if x=2, R.sup.1 is C.sub.2 -C.sub.18 alkylene, C.sub.2 -C.sub.18 alkylene which is interrupted by --NR.sup.5, --O-- or --S--, or is a ##STR3## radical, and, if x=3, R.sup.1 is C.sub.4 -C.sub.12 alkanetriyl or a ##STR4## group in which m is 1-4, are suitable as stabilizers for organic materials which are sensitive to thermal, oxidative and/or photoinduced degradation.

Asymmetric aryl phosphites

Compounds of the formula I ##STR1## in which x is 1, 2 or 3, and, if x=1, R.sup.1 is C.sub.1 -C.sub.30 alkyl, C.sub.1 -C.sub.18 alkyl substituted by halogen, --COOR.sup.2, --CN, --NR.sup.3 R.sup.4 or by --CONR.sup.3 R.sup.4, C.sub.2 -C.sub.18 alkyl which is interrupted by --NR.sup.5 --, --O-- or --S--, C.sub.3 -C.sub.18 alkenyl, C.sub.5 -C.sub.12 cycloalkyl, phenyl-C.sub.1 -C.sub.4 alkyl, phenyl which is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl, halogen, phenyl-C.sub.1 -C.sub.4 alkyl and/or C.sub.1 -C.sub.4 alkoxy, or R.sub.1 is naphthyl, a radical of the formula ##STR2## R.sub.2, R.sub.3, R.sub.4 and R.sub.5, independently of one another, are hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.12 cycloalkyl or phenyl-C.sub.1 -C.sub.4 alkyl, R.sup.6 is hydrogen, methyl, allyl or benzyl, R.sup.7 is hydrogen or --OR.sup.9, R.sup.8 is hydrogen or methyl, R.sup.9 is hydrogen or C.sub.1 -C.sub.30 alkyl, R.sup.10 and R.sup.11, independently of one another, are hydrogen or C.sub.1 -C.sub.8 alkyl, and n is 3-6, with the proviso that R.sup.1 is not a phenyl radical which is substituted in both ortho-positions to the carbon atom bonded to the oxygen atom, if x=2, R.sup.1 is C.sub.2 -C.sub.18 alkylene, C.sub.2 -C.sub.18 alkylene which is interrupted by --NR.sup.5 --, --O-- or --S--, or is a ##STR3## radical, and, if x=3, R.sup.1 is C.sub.4 -C.sub.12 alkanetriyl or a ##STR4## group in which m is 1-4, are suitable as stabilisers for organic materials which are sensitive to thermal, oxidative and/or photoinduced degradation.

2-(2-Hydroxyphenyl)-2H-benzotriazoles of the formula ##STR1## in which R is hydrogen, C.sub.1 -C.sub.12 alkyl or C.sub.1 -C.sub.4 alkoxy, R.sub.1 is hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.6 cycloalkyl, phenyl or phenyl-C.sub.1 -C.sub.4 alkyl and R.sub.2 is C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.6 cycloalkyl, phenyl, phenyl-C.sub.1 -C.sub.4 alkyl or a group --C.sub.n H.sub.2n --COOR.sub.3, in which n is 0 to 4 and R.sub.3 is hydrogen or C.sub.1 -C.sub.12 alkyl, can be prepared particularly advantageously by catalytic hydrogenation of a suitable o-nitroazo compound in the presence of a Pt, Pd, Pt/Pd or Rh hydrogenation catalyst and an alkylenediamine or an acyclic or cyclic polyalkylene polyamine in a halogenated or nonhalogenated aromatic hydrocarbon as solvent.

Process for the preparation of benzotriazoles

A process for the preparation of tris-(2,4-ditert-butylphenyl) phosphite from 2,4-ditert-butylphenol and phosphorus trichloride in the presence of catalysts, which comprises carrying out the reaction in an at least three-stage process in which the 2,4-ditert-butylphenol and 40-100% of the catalyst are combined in a preliminary stage and are brought together with the phosphorus trichloride in a first stage, these being allowed to react under normal pressure and at temperatures of 55.degree. to 70.degree. C. for a dwell time of 15 to 40 minutes, the reaction mixture is then reacted in a second stage under normal pressure and at temperatures of over 140.degree. C., remaining amounts of catalyst being added to the first and/or second reaction stage, the reaction mixture is then kept under reduced pressure at temperatures of at least 186.degree. C. in a third reaction stage, and the tris-(2,4-ditert-butylphenyl) phosphite is then isolated from the reaction mixture, the process being carried out in the absence of solvents.

Process for the preparation of tris(2,4-ditert-butylphenyl)phosphite

A process for the preparation of hydroxybenzylphosphonates of forula ##STR1## by reacting Mannich base of formula ##STR2## with as trialkyl phosphite of formula ##STR3## wherein R.sub.1 and R.sub.2 are each independently of the other C.sub.1 -C.sub.12 alkyl or, when taken together form a piperidinyl or morpholinyl radical, and R.sub.5, R.sub.6 and R.sub.7 are each independently of one another C.sub.1 -C.sub.4 alkyl, which reaction is carried out in the presence of a carboxylic anhydride (IV). The compounds of formula I may suitably be used as processing stabilizers for plastics.

Process for the preparation of sterically hindered

A process for the preparation of compounds of formula I ##STR1## wherein R.sub.1 and R.sub.2 are each independently of the other hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.6 cycloalkyl or phenyl, and R.sub.3 and R.sub.4 are each independently of the other C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.6 cycloalkyl, phenyl, phenyl which is substituted by C.sub.1 -C.sub.6 alkyl and/or hydroxy, or phenyl-C.sub.1 -C.sub.4 alkyl. The process comprises reacting a compound of formula III ##STR2## with a nitrite in aqueous or aqueous/organic medium to a compound of formula II ##STR3## extracting said compound of formula II from the reaction solution with a solvent, hydrogenating said compound, without isolation, in the cited solvent and in the presence of a palladium catalyst, to the corresponding p-aminophenol, and reacting said aminophenol, without isolation, with cyanuric chloride and a compound of formula HSR.sub.3 or HSR.sub.4 or a mixture of compounds of formulae HSR.sub.3 and HSR.sub.4. The products are obtained in high yield and purity.

Process for the preparation of alkylhydroxyanilinothiotriazine

A process for the preparation of 4-hydroxy-2,2,6,6-tetramethyliperidine (HTMP) by hydrogenation of triacetonamine (TAA) in the presence of an Ni, Co, Ru, Rh, Os or Ir hydrogenation catalyst is described. The process is carried out in the melt without a solvent.

Process for the preparation of 4-hydroxy-2,2,6,6-tetramethylpiperidine

A process for the production of alkyltin thiocarboxylic acid esters from alkyltin halides and thiocarboxylic acid esters in the presence of an acid acceptor, which process comprises carrying out the reaction continuously in a reaction system comprising 1 to 5 agitator vessels with an average dwell time of 1 to 60 minutes, at a constant pH value in the range from 3 to 8, and in a temperature range from 40.degree. to 80.degree. C. and separating the product drawn off from the reaction system from the aqueous phase and subsequently drying it. The alkyltin thiocarboxylic acid esters obtained by the process of the invention are used for stabilizing homo- and copolymers of vinyl chloride.

Continuous process for the preparation of alkyltin thiocarboxylic acid

The invention relates to a novel process for the preparation of compounds of the formula I ##STR1## by polycondensation of a diol of the formula II ##STR2## with a dicarboxylic acid ester of the formula III ##STR3## In the above formulae, the substituents and symbols R.sub.1, R.sub.2, R.sub.3 and n are as defined in claim 1. The process comprises stirring the reaction medium which contains an excess of 2 to 50 mol. %, based on the diol of formula II, of the dicarboxylic acid ester of the formula III, in the presence of at least 0.03 mol. % of a suitable catalyst, until the bulk of the alkanol of the formula R.sub.3 OH formed during the reaction is distilled off, under a pressure of 0.7 to 1.3 bar, and thereafter stirring under a pressure of less than 5 mbar, in the temperature range from 100.degree. to 170.degree. C., and subsequently working up the resultant melt in conventional manner.

Process for the preparation of polyesters from aliphatic dicarboxylic

A process for producing triarylphosphites of the formula (RO).sub.3 P, in which R represents aryl or aryl substituted by one or more straight-chain or branched-chain alkyl, cycloalkyl, aryl or aralkyl groups, by reaction of phosphorus trihalides with hydroxy-substituted aromatic compounds of the formula ROH in the presence of 0.005 to 10 mol %, relative to the hydroxy-substituted aromatic compound, of a catalyst, optionally in the presence of a solvent, in which process the catalyst used is a compound from the group comprising amines or ammonium salts, amides of carboxylic and thiocarboxylic acids and also of oxygen acids of phosphorus, non-aromatic nitrogen-containing heterocycles and salts thereof, guanidines, amidines and azomethines and also salts thereof, sulfones, sulfoxides and sulfonium salts, primary, secondary and tertiary phosphines and salts thereof, phosphine oxides, phosphine sulfides or esters of phosphoric acids.

Process for producing triarylphosphites

There is described a continuous process for producing 1,2-alkanediols of the formula ##STR1## in which R is an alkyl group having 3-6 carbon atoms, by reaction of a 1-alkene of the formula

Continuous process for producing 1,2-alkanediols

A process for producing triarylphosphites of the formula (RO).sub.3 P, in which R represents aryl or aryl substituted by one or more straight-chain or branched-chain alkyl, cycloalkyl, aryl or aralkyl groups, by reaction of phosphorous trihalides with hydroxy-substituted aromatic compounds of the formula ROH in the presence of 0.005 to 10 mol %, relative to the hydroxy-substituted aromatic compound, of a catalyst, optionally in the presence of a solvent, in which process the catalyst used is a compound from the group comprising amines or ammonium salts, amides of carboxylic and thiocarboxylic acids and also of oxygen acids of phosphorus, non-aromatic nitrogen-containing heterocycles and salts thereof, guanidines, amidines and azomethines and also salts thereof, sulfones, sulfoxides and sulfonium salts, primary, secondary and tertiary phosphines and salts thereof, phosphine oxides, phosphine sulfides or esters of phosphoric acids.

A process for producing triarylphosphites of the formula (RO).sub.3 P, in which R represents aryl or aryl substituted by one or more straight-chain or branched-chain alkyl, cycloalkyl, aryl or aralkyl groups, by reaction of phosphorus trihalides with hydroxy-substituted aromatic compounds of the formula ROH in the presence of 0.005 to 10 mol %, relative to the hydroxy-substituted aromatic compound, of a catalyst, optionally in the presence of a solvent, in which process the catalyst used is a compound from the group comprising amines or ammonium salts, amides of carboxylic acid and thiocarboxylic acids and also of oxygen acids of phosphorus, non-aromatic nitrogen-containing heterocycles and salts thereof, guanidines, amidines and azomethines and also salts thereof, sulfones, sulfoxides and sulfonium salts, primary, secondary and tertiary phosphines and salts thereof, phosphine oxides, phosphine sulfides or esters of phosphoric acids.

Stabilization of chlorine-containing thermoplasts with 1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylic acid esters alone or, in particular, together with a metal-containing stabilizer as synergist.

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Lorsch/Hessen, Germany

Rudolf Maul