Ciba-geigy Corporation

Huntsman Advanced Materials Americas LLC

Vantico Limited

Roger F Malherbe

Roland A Winter

Michael Rasberger

Raymond R Seltzer

Rudolf A Behrens

Thomas E Conetta

Ramanathan Ravichandran

Martin Roth

Laurenz Gsell

James Peter Galbo

Daniel Bellus

Peter J Schirmann

Qian Tang

Andrew Mar

Catherine Schoenenberger

Michael H Ackerman

Frank Tieh-Yin Fu

Jean-Marc Pfefferle

A process for the preparation of aromatic N-glycidylamines is described, wherein an amine which contains at least one aromatic aminehydrogen atom is heated with at least 0.7 equivalent of epichlorohydrin per aminehydrogen equivalent of the aromatic amine, using a divalent or polyvalent metal salt of nitric acid, as a catalyst, dissolved in propylene carbonate, and the product is then dehydrochiorinated.

Process for the preparation of aromatic N-gylcidyl amines

Curable composition comprising epoxidized natural oils

Hindered amines based on various 2,2,6,6-tetraalkylated nitrogen-containing heterocyclic moieties wherein the hindered nitrogen atom on the ring is substituted with O-acyl, O-carbamoyl or O-carbonate substituents and the 4-position of the ring is substituted with a variety of groups, are effective as light stabilizers in diverse substrate systems.

O-carbonyl N-hydroxy hindered amine stabilizers

N-OR.sub.1 substituted hindered amine light stabilizers impart outstanding stabilization properties to acid catalyzed thermoset coating compositions providing enhanced resistance against the deleterious effects of light, moisture or oxygen without inhibition of cure.

Stabilization of acid catalyzed thermoset resins

N-hydroxy substituted hindered amine light stabilizers impart outstanding stabilization properties to acid catalyzed thermoset coating compositions with enhanced resistance against the deleterious effects of light, moisture or oxygen in the substantial absence of cure inhibition.

Stabilization of acid catalyzed thermoset resins with n-hydroxy hindered

Compounds of the formula (T).sub.g -E where T is a substituted 4-acyl-2-piperazinone group, g is 1 or 2 and E is a selected terminal or linking group, are effective light stabilizers for polyolefins and other organic polymers, particularly thermoset acrylic or alkyd acrylic resins.

Substituted piperazinone light stabilizers

Nitroxyls of the formula ##STR1## where E.sub.1, E.sub.2, E.sub.3 and E.sub.4 are independently an organic radical so that the carbon atoms to which they are attached are each a quaternary carbon and T is a divalent radical are prepared by the oxidation of the corresponding amine in an inert organic solvent with a hydroperoxide in the presence of a metal carbonyl, metal oxide or metal alkoxide catalyst in high yield and purity. The nitroxyls may be directly reduced to the corresponding hydroxylamines by catalytic hydrogenation. The nitroxyls are useful as polymerization inhibitors and the hydroxylamines as polymer stabilizers.

Process for preparing nitroxyls of sterically hindered amines

Compounds of the formula (T).sub.g -E where T is a substituted 4-acyl-2-piperazinone group, g is 1 or 2 and E is a selected terminal or linking group, are effective light stabilizers for polyolefins and other organic polymers.

Polyhydroxylamines are effective in stabilizing polyolefin compositions containing a stabilizer or mixture of stabilizers selected from the group consisting of the phenolic antioxidants, the hindered amine light stabilizers, the alkylated hydroxybenzoate light stabilizers, the ultraviolet light absorbers, the organic phosphorus compounds, the alkaline metal salts of fatty acids and the thiosynergists, against degradation upon high temperature extrusion, exposure to the combustion products of natural gas, gamma irradiation or upon storage for extended periods.

Polyhydroxylamines

Compounds of the formula L-T, where L is an unsubstituted or substituted tetrahydro-1,4-oxazine-2-one group and T is a substituted 4-piperidinyl hindered amine moiety, are effective light stabilizers for polyolefins and other organic polymers.

N-Piperidyl tetrahydro-1,4-oxazin-2-one light stabilizers

Compounds of the formula (L--T).sub.g --E (I) or (L--T--G) .sub.h --Q (II), where L is a lactam group, T is a substituted 4-piperidinyl hindered amine moiety and E or Q are selected linking or terminal groups, are effective light stabilizers for polyolefins and other organic polymers.

N-Piperidyl lactam light stabilizers

Oligomeric esteramides having recurring structural units of the formula ##STR1## where G is a hindered amine radical of formula I or II ##STR2## in which R.sup.1 is hydrogen or alkyl having 1 to 4 carbon atoms, R.sup.2 is hydrogen, alkyl having 1 to 12 carbon atoms, allyl, benzyl, acetyl, acryloyl or cyano, Z.sub.1 is a direct bond, --NHCH.sub.2 CH.sub.2 --, --NHCH.sub.2 CH.sub.2 CH.sub.2 -- or --OCH.sub.2 CH.sub.2 --, Z.sub.2 is ethylene or trimethylene, E is a divalent aliphatic, aromatic or alicyclic radical and L is unsubstituted or substituted alkylene, are useful light stabilizers for plastics.

Oligomeric esteramides containing pendant hindered amine groups

Dihalovinylcyclopropanethiolic acid esters of the formula ##STR1## wherein X.sub.1 represents fluorine, chlorine or bromine, R.sub.1 represents hydrogen, methyl, ethynyl or cyano, and Y represents hydrogen, fluorine, chlorine or bromine, processes for their manufacture, and a method of controlling pests which comprises the use of these compounds.

Dihalovinylcyclopropanethiolic acid esters and their use in pest control

A compound of the formula I ##STR1## in which R.sub.2 is an optionally substituted 4-piperidinyl bonded via oxy or imino, or an optionally substituted 2-(piperidino)-ethoxy, n is 1 or 2, R.sub.7 and R.sub.8 are hydrocarbon radicals, R.sub.9 is hydrogen or methyl, R.sub.14 is cyano, --CH.sub.2 OH, a hydroxymethyl which is C-substituted by an optionally substituted 4-piperidinyl bonded via oxy or imino, or by an optionally substituted 2-(piperidino)-ethoxy, or R.sub.14 is also acyl or nitro, and, when n=1, R.sub.15 is hydrogen, a substituted hydroxybenzyl, an optionally substituted hydrocarbon radical, an optionally substituted 4-piperidinyl, or alkylene which is optionally linked to R.sub.14 and optionally substituted, or, when n=2, R.sub.15 is a direct bond or an optionally interrupted hydrocarbon radical, and its salts as stabilizers for organic material.

Piperidyl esters of phenolalkylene carboxylic acids

Polyalkylpiperidinyl esters of diazocarboxylic acids are prepared, which compounds protect organic polymers against UV light degradation. The light stabilizers have the ability to react with the organic polymeric substrates thus making the piperidinyl esters migration and extraction resistant. Polymers which may be stabilized with the compounds of this invention include polypropylene, polyethylene, polystyrene and polyamides.

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Basel, Switzerland

Roger F Malherbe