Akzona Incorporated

Akzo N.v.

Peter Hope

Paul K Battey

Ashutosh H Sharma

Manfred F Bergfeld

Joseph W Burley

Malcolm G Pritchard

Malcolm Mellor

The present invention relates to a process for the preparation of organic hydroxylamines as a result of the corresponding nitroderivative being hydrogenated in the presence of an inert solvent, a platinum catalyst, a nitrogen-containing base (in an amount of less than 10% by weight calculated on the amount of nitro derivative) and a tri- or pentavalent organic phosphorus compound. It has been found that if only use is made of the nitrogen-containing base or the phosphorus compound the yields of isolated hydroxyl amine are significantly reduced in comparison with those obtained with the present process.

Process for the preparation of a hydroxylamine

There are disclosed novel compounds of the formula: ##STR1## wherein n=0 or 1, R.sub.1 is selected from the group consisting of a hydrogen atom, straight chain and branched chain alkyl groups and alkoxy groups, and cycloalkyl groups and cycloalkoxy groups having 5 to 8 carbon atoms, R.sub.2 is selected from the group consisting of lower alkyl groups having 1 to 5 carbon atoms, X is an oxygen atom if n=0 or a nitrogen atom if n=1, Y is selected from the group consisting of a hydrogen atom, straight chain and branched chain alkyl groups having 1 to 18 carbon atoms, cycloalkyl groups having 5 to 8 carbon atoms, alkenyl groups having 3 to 18 carbon atoms, phenyl groups, alkylphenyl groups having 7 to 14 carbon atoms and aralkyl groups having 7 to 15 carbon atoms, and R.sub.3 is selected from the same group as Y, or together with X and Y forms part of a heterocyclic ring composed of 5 or 6 atoms in which X is the hetero-nitrogen atom. Also disclosed is the use of the foregoing compounds as stabilizers in rubber or rubber latex.

Rubber stabilizers derived from N-phenyl-p-phenylenediamine

Novel phosphoramidates of the general formula: ##STR1## wherein R, R' and R' represent certain specified substituent groups, are useful as stabilizing agents for organic materials, such as natural and synthetic rubbers and lubricating oils. The combined use of these compounds with certain sulfur-containing compounds shows a surprising synergistic effect.

Phosphoramidates containing a p-phenylenediamine group

Novel organotin compounds of the formula: ##STR1## wherein q is 1 or 2; m is 1,2 or 3; R.sub.6 is an alkyl group having from 1 to 18 carbon atoms, a cycloalkyl group having from 3 to 6 carbon atoms, an aryl group, an aralkyl group, and alkaryl group having up to 30 carbon atoms, or a group of the formula: ##STR2## wherein R.sub.7, R.sub.8, R.sub.9 and R.sub.10 are each independently an alkyl group having from 1 to 18 carbon atoms, an oxygen-containing hydrocarbon group or a hydrogen atom, with the proviso that at least one of R.sub.7 and R.sub.8 contains, adjacent to the HC grouping, a carbonyl group which forms part of an acid group, an ester group, and acid halide group, a ketone group or an aldehyde group; when q=1, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5, are, each independently, a hydrogen atom, an alkyl or alkoxy group having from 1 to 14 carbon atoms, a cycloalkyl or cycloalkoxy group, having from 3 to 6 carbon atoms, a nitro group or a halogen atom; and when q=2, m=1, and the two structural units in the para position are interlinked directly or by way of an oxygen atom, a methylene group, an SO.sub.2 group of an isopropylidene group and R.sub.1 R.sub.2 R.sub.4 and R.sub.5 are each as defined above, and a process for making the same. The compounds may be formulated into stabilizer compositions and used to stabilize polyvinyl chlorides and polyvinylidene chloride against heat and light deterioration. They may be used with 2,4,6-trisubstituted phenolic antioxidants, and mono or di-alkyl or ester tin sulphides.

Novel organotin compounds, a process for their preparation and their use

Compositions for stabilizing a vinyl or vinylidene halide polymer or chlorinated polyethylene which comprise a major proportion of (a) at least one ester tin compound, for example .beta.-carboalkoxyethyl tin mercaptides, .beta.-carboalkoxyethyl tin mercapto-acid esters and the like and a minor proportion of (b) at least one unsubstituted or alkyl substituted o-dihydric phenol, such as catechol, t-butyl catechol and 2,3-dihydroxy naphthalene. These compositions synergistically contribute to the heat stability of vinyl or vinylidene halide polymers or chlorinated polyethylene. The performance of the compositions disclosed is particularly improved as regards resistance to early discoloration and long term heat stability of the ester tin compounds contained in them. Moreover, the amounts in which the compounds need be used for stabilization can be kept relatively small.

Compositions for stabilizing a vinyl or vinylidene halide polymer or

An improved process for the preparation of para-nitroso-diphenyl-hydroxylamines is discussed. In the improved process the dimerizing rearrangement of a nitroso benzene is performed in the presence of at least 0.5 mole of a Lewis acid per mole of nitroso compound.

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Littleborough, United Kingdom

Peter Hope