Aryl phosphonites, a process for their production and their use

Details Aryl phosphonites, a process for their production and their use Aryl phosphonites, a process for their production and their use

1992-02-20

1994-03-29

Hoke, Veronica P.

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Processes of preparing a desired or intentional composition...

524291, 524135, 558 70, 558 83, 558 78, 558134, 458156, 458190, C08K 55393, C07F 96574, C07F 948

Patent

active

052985415

DESCRIPTION:

BRIEF SUMMARY
DESCRIPTION

The present invention relates to new diaryl phosphonites and tetraaryl diphosphonites, a process for their preparation and their use for stabilizing plastics, in particular polyolefins.
It is known that synthetic polymers have to be protected against unwanted oxidative, thermal and photochemical damage during the preparation, the processing and the use by means of stabilizers or stabilizer systems. Such stabilizers comprise, for example, a phenolic antioxidant which should ensure in particular the long-term use stability of the molded article, and one or more costabilizers, which control the processing stability and in some cases also reinforce the synergistic effect of the phenolic component.
Conventional stabilizers include ortho-alkylated aryl phosphites and phosphonites, the latter being distinguished in particular by extensive stability to hydrolysis.
It is known from European Patent 5,447 (=U.S. Pat. Nos. 4,406,842 and 4,474,914=Japanese Laid-Open Application 79-141,753) that ortho-alkylated phenyl phosphonites of the formula ##STR2## can be prepared by reaction of alkyl- or arylphosphonous dichlorides with ortho-alkylated phenols in the presence of at least stoichiometric amounts of a suitable base for neutralizing the hydrochloric acid formed. Although the general definitions given in this patent are specified to the extent that within preferred, relatively narrow definitions for the radicals R.sub.1, R.sub.2 and R.sub.3, the radical R.sub.1 can be phenyl, o-, m-, p-tolyl, o-, m-, p-xylyl, mesityl, o-cumyl, p-tert-butylphenyl, 2,4-di-tert-butylphenyl, 2,4,6-tri-tert-butylphenyl, or 2,4-di-tert-octylphenyl, R.sub.2 can be tert-butyl, tert-amyl, tert-octyl, tert-octadecyl and R.sub.3 can be H, methyl, i-propyl, tert-butyl, tert-amyl, n-hexyl, tert-octyl, tert-dodecyl or n-octadecyl, .alpha.-methylbenzyl or .alpha.,.alpha.-dimethylbenzyl; of the possible combinations among these, however, only two embodiment examples where R.sub.1 is phenyl and R.sub.2 and R.sub.3 are simultaneously tert-butyl or tert-octyl are mentioned, and furthermore 6 table examples, in three of which R.sub.1 is also phenyl and either R.sub.2 is tert-octyl and R.sub.3 is methyl or R.sub.2 is tert-butyl and R.sub.3 is hydrogen or R.sub.2 and R.sub.3 simultaneously are .alpha.,.alpha.-dimethylbenzyl. Accordingly, these 5 compounds cannot be deemed new.
However, the process of European Patent 5,447 can be carried out only to a limited extent because of the difficult synthesis of the dichlorophosphanes required as precursors, which is of course a disadvantage if an industrial preparation is taken into consideration. Thus, for example, of the aromatic derivatives, only phenyldichlorophosphane is an industrially available product, which makes derivatives of benzenephosphonous acid only available, which makes it easy to understand why, of the compounds in which R.sub.1 is an aryl radical, precisely only those having unsubstituted phenyl are cited.
However, in order to meet the high demands made in practice on the stability, efficiency, nonvolatility and migration behavior of stabilizers for polymers, it is desirable that especially the more highly substituted derivatives of arylphosphonous acids be available. However, they are not accessible by known processes, due to the fact that until now the preparation of the precursors has not been economically feasible.
As a result, new stabilizers having improved properties and processes for their preparation, which do not have these disadvantages are very desirable.
Accordingly, the present invention relates to aryl phosphonites of the formula V (see formula sheet), i.e. diaryl phosphonites where n=1 and tetraaryl diphosphonites where n=2, in which A is non-existent--i.e. the two rings carry hydrogen--or a divalent hydrocarbon bridge having 1 to 6 carbon atoms which may be substituted by groups mentioned further below under R.sup.1, or is a hetero atom such as oxygen or sulfur, cycloalkylidene having 4 to 8 carbon atoms or phenylalkylidene having 7 to 12 carbon atoms, R.sup.1 as mo

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