Ciba-Geigy Corporation

Peter Hofmann

Paul Dubs

Hans R Meier

Eduard Troxler

Michael Rasberger

Paul A Odorisio

Glen T Cunkle

Rita Pitteloud

Horst Zinke

Hans-Rudolf Meier

Rudolf Maul

Volker Schenk

Don Sabrsula

Jean Rody

Friedrich Karrer

Samuel Evans

Peter Rohringer

Hermann Nachbur

Ivan Orban

Helmut Muller

Werner Stegmann

Armin Hiestand

Rene Berini

Rudolf Loss

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

The invention relates to the novel compound 3,9-bis(1,2,2,6,6-pentamethyl-4-piperidyloxy)-2,4,8,10-tetraoxa-3,9-diphos phaspiro[5,5]undecane of formula I ##STR1## This compound can be used as stabilizer for organic material, especially as processing stabilizer for polyethylene and polypropylene.

N-methylated bis-4-piperidylphosphite

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 formula I ##STR1## wherein n is 2-4, R.sub.1 is alkyl, cycloalkyl, phenylalkyl, phenyl or a radical of formula II ##STR2## R.sub.2, R.sub.3 and R.sub.4 are independently hydrogen, alkyl, cycloalkyl, phenylalkyl or aryl, or R.sub.3 and R.sub.4 together are alkyl, R.sub.5 and R.sub.6 are independently hydrogen, alkyl, cycloalkyl or phenylalkyl, R.sub.7 is hydrogen, alkyl or a group of the formula --(CH.sub.2).sub.k COOR.sub.8, where k is 0-2 and R.sub.8 is hydrogen or alkyl, and T is an n-valent hydrocarbon radical which may be interrupted by heteroatoms, are useful stabilizers for substrates subject to the deleterious effects of oxygen, heat and/or actinic radiation.

Compositions stabilized with poly-1,3,2-oxazaphospholidines

Compounds of formula I ##STR1## wherein n is 2-4, R.sub.1 is alkyl, cycloalkyl, phenylalkyl, phenyl or a radical of formula II ##STR2## R.sub.2, R.sub.3 and R.sub.4 are independently hydrogen, alkyl, cycloalkyl, phenylalkyl or aryl, or R.sub.3 and R.sub.4 together are alkylene, R.sub.5 and R.sub.6 are independently hydrogen, alkyl, cycloalkyl or phenylalkyl, R.sub.7 is hydrogen, alkyl or a group of the formula --(CH.sub.2).sub.k COOR.sub.8, where k is 0-2 and R.sub.8 is hydrogen or alkyl, and T is an n-valent hydrocarbon radical which may be interrupted by heteroatoms, are useful stabilizers for substrates subject to the deleterious effects of oxygen, heat and/or actinic radiation.

Poly-1,3,2-oxazaphospholidine stabilizers

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

Compounds of the formula I or II, ##STR1## wherein m is 1 or 2, A is branched or unbranched 1,2- or 1,3-alkylene, or o-phenylene, E is a group III or IIIa, R is hydrogen or methyl, R.sup.1 and R.sup.3 are hydrogen, alkyl, alkenyl, aralkyl, alkanoyl, alkenoyl, benzoyl or cyanomethyl, R.sup.2 is a radical of valency m and R.sup.4 is a monovalent radical, are effective processing stabilizers for polymers, in particular for polyolefins, and additionally have a stabilizing action against damage by light.

Selected

s-Triazine compounds, the molecule of which contains at least one ethylenically unsaturated group and at least one 2,2,6,6-tetramethylpiperidine group can be grafted onto organic polymers, in particular onto polyolefines, in the presence of free-radical formers or by means of irradiation. Examples of free-radical formers are peroxy or azo compounds. If polyunsaturated piperidine-triazine compounds are used, it is also possible to achieve crosslinking of the polymer, particularly in the case of polyethylene.

Process for chemically bonding stabilizers to polymers

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

Certain

The incorporation of sterically hindered piperidine derivatives into polyurethanes protects this polymer material against light degradation. Usable for the incorporation are piperidine derivatives which are at least difunctional towards isocyanates and contain the structure ##STR1## wherein R is hydrogen or alkyl having 1 to 5 carbon atoms.

Modified polyurethanes with increased light stability

A process for flameproofing polyurethanes, particularly polyurethane foams, is provided. It consists in adding a reaction product from dimethyl methanephosphonate, an aliphatic diol or triol and a lower epoxide to the polyurethane components. These reaction products are non-uniform mixtures of different esters of methane phosphonic acid.

Process for flameproofing polyurethanes

Composition for flameproofing organic fibre material which contains at least

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Basel, Switzerland

Peter Hofmann