Ciba-geigy Corporation

Paul Moser

Jean Rody

Michael Rasberger

Helmut Muller

Friedrich Karrer

Samuel Evans

Hanns Lind

Helmut Linhart

Helmut Mueller

Johann Rody

Polypropylene compositions containing as stabilizer at least one compound of the formula I ##STR1## in which x is 0 or 1,

Stabilized polypropylene

Novel ligands of the general formula wherein r is 1 or 2, and L is a piperidine which is substituted by at least one enolate group in the 1-position or 4-position and wherein the ring nitrogen is sterically hindered by alkyl substituents in the adjacent positions. These ligands are useful in preparing light stabilizers.

Hindered piperidine ligands

Compounds of the formula I ##STR1## in which m is 0 or 1 and n is 1 or 2 and R, R.sup.1, R.sup.2, Z and X are as defined in claim 1, and also salts of these compounds, are valuable light stabilizers for organic materials, especially for polymers. The compounds of the formula I can be prepared from the corresponding 4-sec.-aminopiperidines by reaction with cyclic dicarboxylic acid anhydrides and appropriate further reactions.

Amide derivatives of polyalkylpiperidines

Metal phenolates having at least one piperidinyl group sterically hindered on the nitrogen atom are suitable as additives for organic material.

Novel metal complexes

Mixtures of a polymer which contains polyalkylpiperidines chemically bonded in any form and a metal compound MeL.sub.w, in which Me is a divalent or trivalent metal ion or a divalent oxo-metal ion or a divalent dialkyl-tin ion, L is the monovalent anion of a carboxylic acid, of a phosphinic acid or of a phosphonic acid monoester or of an enol and w is 2 or 3, are effective light stabilizers for plastics. The piperidine-containing polymers can be, for example, polyesters, polyamides, polyamines, polyaminotriazines or poly(meth)-acrylates. Examples of metal compounds MeL.sub.w are nickel oenanthate or nickel acetylacetonate. Plastics to be stabilized are in particular the polyolefins.

Novel light stabilizers for plastics

Nickel complexes containing ortho- or para-hydroxybenzoate anions and a non-ionic amine ligand are valuable light-stabilizers for polymers, particularly for polyolefins. The complexes may also contain a second carboxylate anion, different from the benzoate anion, and in this case also the amine-free nickel compounds show a high stabilizing action.

Nickel stabilizers for synthetic polymers

Novel compounds of the general formula I ##STR1## wherein M.sup.q.sym. is a metal ion carrying a double or triple positive charge and q is 2 or 3 and r is 1 or 2, the quotient q/r being 1, 1.5, 2 or 3, and L is a piperidine which is substituted by at least one enolate group in the 1-position or 4-position and wherein the ring nitrogen is sterically hindered by alkyl substituents in the adjacent positions, and m is 0, 1 or 2 and A is H.sub.2 O or an amine.

Novel light stabilizers

Novel light stabilizers, i.e. metal complexes of formula I ##STR1## wherein Me is a doubly or triply positively charged metal ion,

Metal salts of monoalkyl .alpha.-aminophosphonates or of .alpha.-aminophospinates show a considerable thermostability. Obviously the amino groups are coordinated on the metal atom. These complex salts are soluble in organic solvents and compatible even with non-polar plastics such as polyolefins. They are effective stabilizers against the light-induced deterioration of polymers with an outstanding duration of this activity. The cation of these salts may be a complex-forming multivalent metal, preferable nickel, cobalt, zinc and aluminum. The amino group may be primary, secondary or tertiary. The complex salts are prepared according conventional processes, for example by conversion of the corresponding alkali phosphonate with a metal halide in organic solution.

Metal complexes of .alpha.-aminophosphonic acid half-esters and of .alpha.-

The invention relates to compounds of the general formula I ##STR1## wherein R.sub.1 and R.sub.2 independently of one another are C.sub.1 -C.sub.8 -alkyl, C.sub.5 -C.sub.8 -cycloalkyl or C.sub.7 -C.sub.9 -aralkyl,

New stabilizers

New amino phosphonates, containing 2,2,6,6-tetrasubstituted-piperidino moieties and processes for their manufacture are disclosed. These compounds are employed to stabilize organic materials such as polyolefins, polyamides and polyurethanes against degradation from the action of oxygen, heat and light.

Phosphonate stabilizers

Mixtures consisting of a compound of the formula I ##STR1## wherein either R.sub.1 represents a hydroxyl group and R.sub.2 represents hydrogen or R.sub.1 represents hydrogen and R.sub.2 represents a hydroxyl group, R.sub.3 and R.sub.4 independently of one another represent hydrogen or alkyl, and n represents a value from 0 to 2, and a compound of the formula II ##STR2## wherein R.sub.5 represents alkyl, cycloalkyl, aralkyl, aryl or aralkyl or aryl groups which are mono-, di or tri-substituted by hydroxyl, alkyl, chlorine and/or alkoxy groups, alkoxy, cycloalkoxy, aralkoxy, aryloxy or aralkoxy or aryloxy which are mono-substituted or di-substituted in the aryl radical by alkyl, chlorine and/or alkoxy, R.sub.6 represents hydrogen, alkyl, cycloalkyl, aralkyl, aryl or aralkyl or aryl groups which are mono-, di- or tri-substituted by hydroxyl, alkyl, chlorine and/or alkoxy groups, alkoxy, cycloalkoxy, aralkoxy, aryloxy or aralkoxy or aryloxy which are mono-substituted or di-substituted in the aryl radical by alkyl, chlorine and/or alkoxy, and m represents a value from 0 to 2.5, are valuable for stabilizing polymeric substrates.

Nickel complexes containing ortho- or para-hydroxy-benzoate anions and a non-ionic amine ligand are valuable light-stabilizers for polymers, particularly for polyolefins. The complexes may also contain a second carboxylate anion, different from the benzoate anion, and in this case also the amine-free nickel compounds show a high stabilizing action.

New complexes of nickel salts of hydroxybenzoic acids are stabilizers for polymers. The complexes are prepared by reacting a nickel benzoate with a corresponding alcohol.

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Riehen, Switzerland

Paul Moser