Ciba-geigy Corporation

Ciba Geigy Corporation, N.y.

Eduard Troxler

Rudolf Maul

Ivan Orban

Peter Hofmann

Bernard Hugelin

Dieter Reinehr

Rita Pitteloud

Horst Zinke

Volker Schenk

Paul Dubs

Hans-Rudolf Meier

Thomas Kainmuller

Werner Stegmann

Bernhard Medinger

Christian Luthi

Heinz Peter

Werner H Dorfel

Dieter Reinchr

Anton Meier

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.

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

If the transesterification of esters of the formula ##STR1## with alcohols of the formula III A--(OH).sub.m is catalyzed by successive treatment with catalytic amounts (a) of a tin compound of a metal of the fourth main group or the fourth sub-group of the periodic system and (b) of an acid earth, compounds of the formula I ##STR2## are obtained in virtually quantitative yield. The products thus obtained contain no troublesome by-products and do not have to be additionally purified. R is methyl or ethyl, A is a radical derived from an m-hydric aliphatic alcohol, n is 0 to 2, and m is 1 to 4.

Process for the preparation of sterically hindered

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

The known reaction of dichlorotriazines of the formula II ##STR1## in which Q is an ether or amino radical, with diamines of the formula III

Process for the preparation of polyaminotriazines

Mixtures of esters of polyalkylpiperidine derivatives, of the formulae I and II ##STR1## in which the proportions of I to II are 95 to 70% by weight and 5 to 30% by weight, are obtained by reacting about 2 mols of a piperidine of the formula III ##STR2## with 0.9 to 1.3 mols of a diester of the formula IV ##STR3## in the melt at between 100.degree. and 145.degree. C., in the presence of an alkali metal amide as a catalyst. The mixtures of esters thus obtained are very suitable as light stabilizers for plastics.

Process for the preparation of novel light stabilizers

New nonadienylamines, nonatrienylamines and nonylamines are described, as well as a new process for their manufacture by reacting a 1,3-diolefine with a Schiff's base in the presence of certain nickel catalysts. The new compounds are suitable for combating micro-organisms, for example in the protection of materials.

Nonylamines

A process for producing a granulate of difficultly fusible additives for plastics, particularly of pigments, by thermal tumbling granulation, which process comprises mixing the additive in powder form with a granulating auxiliary which softens between 30.degree. and 200.degree. C. and which has a particle size of 0.1-2.0 mm; and subjecting this mixture to a gentle rotary motion, with heating by means of a source of heat being simultaneously applied at least until softening of the granulating auxiliary commences.

Thermal tumbling granulation

A process for producing piperidines of the formula (I) ##STR1## in which R.sub.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl, from a ketone of the formula (II) R.sub.1 --CH.sub.2 --C(O)--CH.sub.3, wherein R.sub.1 has the meaning given above, and ammonia, in which process there is used as catalyst a strongly acid ion exchanger having a medium or large mesh size or having large macropores.

Process for preparing 2,2,6,6-tetraalkyl-4-oxopiperidines

(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 invention relates to curable mixtures which contain 1,10-substituted 1,10-diaminodecanes, as the curing agents, new 1,10-substituted 1,10-diaminodecanes and a process for the manufacture of the latter. The new 1,10-diaminodecanes are manufactured by catalytic hydrogenation of corresponding 3,12-substituted 1,2-diazo-1,5,9-cyclododecatrienes in the presence of an inert organic solvent, while raising the temperature to at least 120.degree. C.

Curable mixtures

New unsaturated 1,2-diazacyclododecanes, more particularly 1,2-diazacyclododecatrienes-1,5,9 and 1,2-diazacyclododecanes-1 and a novel process for the preparation thereof are disclosed which process comprises reacting a 1,3-diolefin with an azine in the presence of certain nickel catalysts. Said process unexpectedly yields 12-membered ring compounds only, and more especially oligomerization products of 2 mols of a 1,3-diolefin and 1 mol of an azine, while deactivation of the nickel catalyst by the -N=N-bond is avoided.

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Basel, Switzerland

Eduard Troxler