Sankyo Company, Limited

Ciba-geigy Corporation

Konishiroku Photo Industry Co., Ltd.

Nobuo Soma

Tomoyuki Kurumada

Takao Yoshioka

Syoji Morimura

Jean Rody

Heimo Brunetti

Tsuneo Wada

Isao Kawamoto

Tomio Nakajima

Shizuo Saito

Hiroyuki Inokuma

Koichi Horigome

Sadao Sugita

Yukio Morifuji

Syoji Moromura

Polymers containing polyalkylpiperidines, preparation and use thereof as stabilizers for synthetic polymer compositions are described. In said polymer, sterically hindered polyalkylpiperidines are laterally linked to the main chain. The polymers are distinguished by an improved stabilizing effect in various synthetic polymer compositions, such as polyolefins, against light- and/or heat-induced deterioration thereof. The polyalkylpiperidine-containing polymers of the invention are hardly volatile upon heat-processing or during storage of shaped articles containing said polymers, and are resistant to extraction with solvents.

Polyalkylpiperdine side chain stabilizers for synthetic polymer

Piperidine derivatives in which two or three piperidine residues each substituted at the 2- and the 6-position by two methyl groups or by one methyl group and one ethyl group, the piperidine residues being attached by means of substituted alkylene groups, by means of polyoxyalkylene groups (whose oxyalkylene chain is optionally interrupted by one or more phenylene or cyclohexylene groups), by means of substituted isocyanurate groups or by means of glyceryl groups, and acid addition salts thereof are valuable as stabilizers for synthetic polymers.

Piperidine derivatives and their use as polymer stabilizers

The invention entitled 'Polymers containing polyalkylpiperidines and use thereof as stabilizers' provides a class of polymers in which groups containing sterically hindered polyalkylpiperidines are linked in the main chain of the polymers via bridging members containing 2-hydroxy-1,3-trimethylene groups. The polymers show superior stabilizing effects for various synthetic polymers such as polyolefins against degradation thereof induced by light and/or heat. The polymers have advantages, as compared with known stabilizer compounds, that they hardly volatile upon processing with heating or during storage of articles containing thereof, and that they are resistant to extraction with solvents from articles containing thereof.

Polymers containing polyalkylpiperidines and use thereof as stabilizers

2,2,6,6-Tetramethylpiperidine derivatives having the formula ##STR1## wherein: X represents a group of formula ##STR2## R represents a hydrogen atom, methyl group, ethyl group, phenoxymethyl group or phenyl group;

2,2,6,6-Tetramethylpiperidine derivatives

Novel piperidine-spiro-hydantoin derivatives represented by the general formula (I) and use thereof as light stabilizers for synthetic polymers are described: ##STR1## The compounds are distinguished by an improved stabilizing effect in various synthetic polymer compositions, such as polyolefins, against light- and/or heat-induced deterioration thereof, small volatility upon heat-processing or during storage of shaped articles containing the compounds, and resistance to extraction with water and solvents.

Piperidine-spiro-hydantoin derivatives and their use as polymer

Derivatives of sterically hindered 4-aminopiperidines are effective as light-stabilizers for organic polymers, especially for polyolefins. The piperidine ring is substituted with at least five alkyl groups, preferably methyl and ethyl groups. The 4-amino group is substituted with mono- or divalent acyl groups. The nitrogen in 1-position may also be substituted with a monovalent organic substituent. The compounds can be synthesized starting from higher homologs of acetone in sequence of several reaction steps.

Derivatives of 4-aminopiperidine as stabilizers for polymers

New polyalkylated 4-aminopiperidine derivatives contain in their molecule two or three piperidine rings, each having two alkyl substituents at both the 2- and the 6- positions, optionally having substituents at the 1- and 3- positions and having an amino substituent at the 4- position. The piperidine rings are joined together by attachment of the 4-amino substituents through, where there are two piperidine rings, a polyalkylene, polyether or polyester chain, or through, where there are three piperidine rings, an isocyanurate or glycerol system. These compounds and their acid addition salts are useful as stabilizers for synthetic polymers.

Polyalkylated 4-aminopiperidine derivatives

Hydantoin derivatives in which two or three piperidine spiro hydantoin residues are attached by means of substituted alkylene groups or polyoxyalkylene groups whose oxyalkylene chain is optionally interrupted by one or more phenylene or cyclohexylene groups or by means of substituted isocyanurate or glyceryl groups and, where they exist, acid addition salts thereof, are valuable as stabilizers for synthetic polymers.

Hydantoin derivatives and their use as polymer stabilizers

Polymers, both natural and synthetic, are stabilized against the deterioration resulting from heat and/or light by the incorporation of certain 2,2,6,6-tetra-substituted-4-piperidinol derivatives which additionally have an alkyl, alkenyl, alkynyl or aralkyl substituent at one or both of the 3- and 5- positions.

Stabilization of synthetic polymers by penta-or-hexa-substituted

Sterically hindered piperidines having at least 5 alkyl groups in ring positions 2,3,5 and 6 are usable as light-stabilizers for organic polymers. The nitrogen may be unsubstituted or may bear a mono- to tetravalent substituent. The compounds can be synthesized by a Wolf-Kishner reduction of polyalkyl 4-oxopiperidines optionally followed by a N-substitution reaction in a second step. The stabilizers are added to the polymers in an amount of from 0.01 to 5% by weight. Preferred is the stabilization of polyolefins, styrene polymers, polyamides and polyurethanes.

Stabilization of poly(mono-olefins)

Novel derivatives of 4-amino-2,6-dimethylpiperidine have additional methyl or substituted-methyl substituents at positions 2 and 6, and a carboxylate ester substituent at position 4. Positions 1 and 3, and the amino group at position 4, can optionally also be substituted. These derivatives are useful for stabilizing synthetic polymers, especially polyolefins, polyamides and polyurethanes, against photo- and thermal-deterioration, generally in an amount of 0.01 - 5.0% by weight based on the polymer.

Synthetic polymer stabilizers

Cyclic ketals of sterically hindered 4-oxopiperidines are effective light-stabilizers for organic polymers. These compounds have at least five alkyl groups in ring positions 2,3,5 and 6 and four alkyl groups in ring positions 2 and 6, preferably methyl and ethyl groups. The ring nitrogen may be unsubstituted or substituted with a monvalent substitutent. The new compounds can be synthesized by ketalization of the corresponding 4-oxopiperidines with diols, triols or tetrols. Using triols the obtained ketals possess hydroxyl groups which may be esterified or etherified in a subsequent reaction step. Ketalization with tetrols yields cyclic bis-ketals.

Derivatives of 4-oxopiperidines and their use as polymer stabilizers

Novel 7,7,9,9-tetra-substituted-1,3,8-triazaspiro�4.5!decane-2,4-diones having an alkyl or allyl group at either the 6- or the 10- position are useful for the stabilization of polymers against photo- and thermal- deterioration.

1,3,8-Triazaspiro�4.5!decane-2,4-dione polymer stabilizers

Stabilization of polymers by penta- or hexa-substituted 4-piperidinol

New 2,2',6,6'-tetraalkyl-2,2',6,6'-tetramethyl-4,4'-bipiperidylidene derivatives, which are optionally substituted in the 1,1',3,3',5, and 5' positions are useful as stabilizers of organic substrates, particularly synthetic polymers, against photo- and thermal-deterioration. They may be prepared by condensing a corresponding 2,6-dialkyl-2,6-dimethyl-4-piperidone and then optionally introducing the desired substituents at the 1- and 1'-positions in the resulting bipiperidylidene derivative.

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Nobuo Soma