Ciba-geigy Corporation

Ciba Specialty Chemicals Corporation

Ivan Orban

Jean Rody

Martin Holer

Valerio Borzatta

Heimo Brunetti

Eduard Troxler

Hanns Lind

Piero Piccinelli

James Peter Galbo

Jean-Pierre Wolf

Nicola Lelli

Michael Ackerman

Samuel Evans

Michael Rasberger

Paul Dubs

Rinaldo Husler

Hans-Rudolf Meier

Peter Hofmann

Werner Fussenegger

Andre Kaufmann

Block oligomers containing 1-hydrocarbyloxy-2,2,6,6-tetramethyl-4-piperidyl groups as stabilizers for organic materials

2-(2,4-Dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-s-triazine is prepared by reacting cyanuric chloride with m-xylene at a temperature of 0.degree.-110.degree. C. in the presence of a Lewis acid and at least one inert chlorinated aromatic solvent to give the intermediate 2-chloro-4,6-bis(2,4-dimethylphenyl)-s-triazine. This intermediate, without being isolated, is then reacted with resorcinol to give the final desired product 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-s-triazine in good yield.

Process for the preparation of

The invention relates to a process for the preparation of thiophene-2,5-dicarboxylic acid by reacting thionyl chloride and adipic acid, with pyridine as catalyst, which process comprises

Process for the preparation of thiophene-2-5-dicarboxylic acid and the

The invention relates to a process for the preparation of polyalkylated aromatic carboxylic acids of formula I ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are each independently of one another hydrogen, C.sub.1 -C.sub.20 alkyl, halogen or C.sub.5 -C.sub.8 cycloalkyl, with the proviso that at least two of the substituents R.sub.1, R.sub.2, R.sub.3, R.sub.4 or R.sub.5 are alkyl and/or cycloalkyl, by reacting corresponding aromatic hydrocarbons with carbon dioxide, which reaction is carried out observing special ratios of temperature and pressure. The invention furthermore relates to a one-pot process for the preparation of the corresponding acyl halides.

Process for the preparation of alkylated aromatic carboxylic acids and

A process for the preparation of compounds of the formula I is described ##STR1## in which R.sup.1 and R.sup.2 independently of one another are C.sub.1 -C.sub.7 alkyl; and R.sup.3 is hydrogen or halogen, by reaction of a diazonium salt of a 2-nitroaniline in acid aqueous solution with a phenol dispersed in water. The process comprises employing as the dispersant a C.sub.8 -C.sub.20 alkanesulfonic acid or a corresponding alkanesulfonate or a mixture of sulfonic acid and sulfonate together with a polyvinyl alcohol. The resulting compounds of the formula I can advantageously be reacted further to give benzotriazoles of the formula V ##STR2## which are used as light stabilizers.

Azo coupling of 2-nitroanilines with 2,4,-disbustituted phenols

Process for the methylation of compounds at least one group of the formula (I) ##STR1## by means of a mixture of formaldehyde and formic acid in a reaction medium consisting of an aromatic hydrocarbon solvent.

Process for the methylation of triazine compounds containing

If the transesterification of esters of formula II ##STR1## with alcohols of formula III A--OH).sub.m is catalysed by treatment with catalytic amounts of an organic or inorganic zinc salt and the resultant melt is subsequently distilled in a short-time distillation apparatus under specific conditions, then compounds of the formula ##STR2## are obtained in virtually quantitative yield, in which formulae I, II and III n is a number from 0 to 2, m is 1 or 2, A is a radical derived from an m-valent aliphatic alcohol, which radical contains 2 to 18 carbon atoms, B is methyl or tert-butyl and R is methyl or ethyl. The products thus obtained contain no troublesome by-products and do not have to be additionally purified.

Process for the preparation of sterically hindered

Compounds of formula I ##STR1## wherein R.sub.1, R.sub.2 and A are essentially hydrocarbyl or substituted hydrocarbyl groups with at least one of R.sub.1 and R.sub.2 being cyclohexyl, n is 0, 1 or 2, m is an integer of 1 to 4 and X is oxygen or --N(R.sub.3)-- wherein R.sub.3 is hydrogen, C.sub.1 -C.sub.4 alkyl or phenyl.

Ortho cyclohexyl, para hydroxy aralkanoic acid esters and amide

Seeding a melt of pentaerythritol tetrakis-[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] with a small amount of the crystalline .beta.-, .delta.- or .lambda.-modification of this compound in an extruder, kneader or internal mixer at 70.degree.-130.degree. C. gives, within a few minutes, pure crystalline product without the use of a hitherto mandatory and environmentally undesirable solvent. Also described is a novel crystalline thermostable .lambda.-modification of pentaerythritol tetrakis-[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate].

Solvent-free crystallization of pentaerythritol

If the transesterification of esters of the formula II ##STR1## with alcohols of the formula III ##STR2## is catalyzed by treatment with catalytic amounts of an oxide or an organo-metallic compound of a metal of the fourth main group or subgroup of the periodic system, and if the resulting melt is then distilled in a flash distillation apparatus under specific conditions, compounds of the formula ##STR3## are obtained in a virtually quantitative yield. In the above formulae, R is methyl or ethyl, A is a radical of an m-hydric aliphatic alcohol, E is methyl or tert-butyl, m is 1 to 4 and n is 0 to 2. The products thus obtained do not contain any interfering by-products and do not have to be additionally purified.

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.

A novel process for producing 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## R.sub.1 and R.sub.2 are independently alkylene or alkenylene, R.sub.3 is lower alkyl and n is 18 to 25. The process according to the invention is characterized in that the reaction medium is treated, in the presence of at least 0.05 mol %, relative to the diol of the formula II, of an organometallic compound of titanium or tin, at a maximum steam temperature of 75.degree. C., until the formed methanol has been almost completely distilled off; distillation is then continued for at least 3 hours, during which time the volume of the reaction solution is kept approximately constant by successive additions of solvent, at a steam temperature of between 100.degree. and 145.degree. C.; the reaction solution is subsequently concentrated by evaporation, and the melt which remains is finally ground after it has solidified. There are thus surprisingly obtained, in practically quantitative yield, polyesters of the formula I having a mean molecular weight Mn of at least 5000.

Process for producing polyesters from aliphatic dicarboxylic acids and

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

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.

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Basel, Switzerland

Ivan Orban