Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...
Patent
1992-12-23
1994-10-18
Hoke, Veronica P.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Processes of preparing a desired or intentional composition...
558 82, 558134, C07B 4900, C07F 96574, C08K 55377
Patent
active
053569679
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel 6-aryl-6H-dibenzo-[c,e][1,2]oxaphosphorines, to a process for their preparation, and to their use for stabilizing plastics, in particular polyolefins.
It is known that synthetic polymers must be protected by stabilizers or stabilizer systems against undesired oxidative, thermal and photochemical damage during preparation, processing and use. Such stabilizers comprise, for example, a phenolic antioxidant, which is intended, in particular, to ensure the running time stability in use of the finished part, and one or more costabilizers, which regulate the processing stability and in some cases also synergistically increase the action of the phenolic component.
Conventional costabilizers include, for example, ortho-alkylated aryl phosphites and phosphonites.
Although the diaryl phosphonites described in European Patent 5 447 have adequate properties as stabilizers for certain areas of application, their synthesis starts from organodichlorophosphines which are poorly accessible in industry. In practice, the only industrially available precursor is dichlorophenylphosphine, which is the only possible precursor to derivatives of benzenephosphonous acid. However, to achieve the desired properties, it is frequently desirable to have precisely compounds containing higher substituted aryl groups on the phosphorus available.
A further serious disadvantage is the necessity to neutralize hydrogen chloride liberated during the synthesis by means of a suitable auxiliary base. In the recycling thereof, the inevitable formation of two equivalents of the corresponding salt is unavoidable.
The phosphonites prepared in German Offenlegungsschrift 2 034 887 by hydrolysis, esterification, transesterification, alkylation or sulfation of 6-chlorodibenzo[c,e][1,2]oxaphosphorine have, inter alia, disadvantages with respect to shelf life, color behavior and hydrolysis resistance, as has already been described in U.S. Pat. No. 4,185,006.
The object of the present invention was therefore to provide novel phosphorus stabilizers which, on the one hand, satisfy the high demands of practice and in particular do not decompose into a plurality of fragments and/or acidic secondary products, even on contact with water, but at the same time can be prepared simply and in high yield by ecologically favorable processes.
Surprisingly, it has now been found that cyclic phosphinous acid esters of the formula I ##STR2## meet these requirements very well.
The invention thus relates to dibenzo[c,e][1,2]oxaphosphorines of the formula I, i.e. aryl-6H-dibenzo[c,e][1,2]oxaphosphorines where n=1 and arylbis{6H-dibenzo[c,e][1,2]oxaphosphorines} where n=2, in which R.sup.1, as a monovalent radical, is a phenyl radical, which may carry 1 to 3 substituents, or a naphthyl radical, which may carry 1 to 5 substituents, the substituents being identical or different nonaromatic hydrocarbon, alkoxy, alkylthio or dialkylamino radicals, in each case having 1 to 8 carbon atoms, aryl or aryloxy, in each case having 6 to 10 carbon atoms, or halogen having an atomic number of from 9 to 35, or, as a divalent radical, is a phenylene or biphenylene radical which is unsubstituted or substituted by up to 4 nonaromatic hydrocarbon radicals having 1 to 8 carbon atoms, or is a naphthylene radical which is unsubstituted or carries 1 to 4 nonaromatic hydrocarbon radicals having 1 to 8 carbon atoms as substituents.
Specific examples of R.sup.1 as a monovalent radical are the various tolyl radicals, xylyl radicals, mesityl, 2,4,5-trimethylphenyl, the various tert.-butylphenyl radicals, di-tert.-butylphenyl radicals, 2,4,6-tri-tert.-butylphenyl, 2,4-di-tert.-octylphenyl, and the various biphenyl, methylnaphthyl, dimethylnaphthyl and trimethylnaphthyl radicals.
Specific examples of R.sup.1 as a divalent radical are the various phenylene radicals, such as 1,3- and 1,4-phenylene, the various biphenylene radicals, such as 2',3-, 2',4-, 3',3-, 3',4- and 4,4'-biphenylene, and the various naphthylene radicals, such as 1,4- and 1,6-naphthylene.
The invention
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Bohshar Manfred
Kleiner Hans-Jerg
Pfahler Gerhard
Hoechst Aktiengesellschaft
Hoke Veronica P.
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