Beta crystalline modification of 2,2',2"-nitrilo[triethyl-tris-(3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl- 2,2'-diyl) phosphite]
AssigneeCiba-Geigy Corporation
InventorsStephen D. Pastor, Sai P. Shum
Life of this patent
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Abstract
The beta crystalline modification of 2,2',2"-nitrilo[triethyl-tris-(3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2, 2'-diyl) phosphite] is obtained by crystallizing said compound from the melt at elevated temperatures. The beta crystalline form is an effective process stabilizer for polyolefins, particularly polypropylene.
Claims11
A process for the preparation of the beta, triclinic crystalline form of the compound 2,2',2"-nitrilo[triethyl-tris-(3,3',5,5'-tetra-tetra-butyl-1,1'-biphenyl-2 ,2'-diyl)phosphite], characterized by melting in the range of 200.degree.-270.degree. C. and by an X-ray diffraction pattern exhibiting lines of very high intensity at 8.4 and 17;
- lines of high intensity at 9.9, 10.6, 11.4, 17.5, 19.1, 20.2;
- lines of medium intensity at 4.6, 4.9, 7.1, 12.7, 13.2, 13.6, 15.3, 15.8, 16.4, 16.7, 18.4, 19.7, 21.7, 23.4;
- and lines of weak intensity at 7.8, 8.8, 9.4, 12, 14.1, 14.6, 21, 22.3, 23.9, 24.7, 25.3, 25.5, 26.4, 27, 27.7, 28.4 and a relative absolute configuration of the three stereo axes of the dibenzo[d,f][1,3,2]dioxaphosphepin rings of R*,R*,S*, which comprises
- crystallizing or recrystallizing said compound from a mixture of benzene, toluene, o-xylene, m-xylene, p-xylene, 1,2,3-trimethylbenzene, 1,3,5-trimethylbenzene, 1,2,4-trimethylbenzene, 1,2,4,5-tetramethylbenzene, ethylbenzene, cumene, o-cymene, m-cymene, p-cymene, o-diisopropylbenzene, m-diisopropylbenzene or p-diisopropylbenzene and 1-butanol, 2-butanol, tert-butanol alcohol, iosbutanol, amyl alcohol, 1-hexanol, 2-ethylhexanol or 1-octanol;
- from a mixture of acetone;
- 2-butanone, 2-pentanone, 3-pentanone or 2-heptanone and methanol, ethanol, 1-propanol, isopropanol, 1-butanol, 2-butanol, tert-butyl alcohol, isobutanol, amyl alcohol, 1-hexanol, 2-ethylhexanol or 1-octanol;
- or from a mixture of benzene, toluene, o-xylene, m-xylene, p-xylene, 1,2,3-trimethylbenzene, 1,3,5-trimethylbenzene, 1,2,4-trimethylbenzene, 1,2,4,5-tetramethylbenzene, ethylbenzene, cumene, o-cymene, m-cymene, p-cymene, o-diisopropylbenzene, m-diisopropylbenzene or p-diisopropylbenzene and acetone, 2-butanone, 2-pentanone, 3-pentanone or 2 heptanone.
A process for stabilizing an organic material against oxidative, thermal or actinic-induced degradation, which comprises
- incorporating therein or applying thereto an effective stabilizing amount of the beta, triclinic crystalline form of 2,2',2"-nitrilo[triethyl-tris-(3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2, 2'-diyl)phosphite], characterized by melting in the range of 200.degree.-207.degree. C. and by an X-ray diffraction pattern exhibiting lines of very high intensity at 8.4 and 17;
- lines of high intensity at 9.9, 10.6, 11.4, 17.5, 19.1, 20.2;
- lines of medium intensity at 4.6, 4.9, 7.1, 12.7, 13.2, 13.6, 15.3, 15.8, 16.4, 16.7, 18.4, 19.7, 21.7, 23.4;
- and lines of weak intensity at 7.8, 8.8, 9.4, 12, 14.1, 14.6, 21, 22.3, 22.8, 23.9, 24.7, 25.3, 25.5, 26.4, 27, 27.7, 28.4 and a relative absolute configuration of the three stereo axes of the dibenzo[d,f][1,3,2]dioxaphosphepin rings of R*,R*,S*.
A composition stabilized against thermal, oxidative and actinic induced degradation which comprises
- (a) an organic material subject to thermal, oxidative and actinic induced degradation, and
- (b) an effective stabilizing amount of the beta, triclinic crystalline form of 2,2',2"-nitrilo[triethyl-tris-(3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2, 2'-diyl)phosphite], characterized by melting in the range of 200.degree.-207.degree. C. and by an X-ray diffraction pattern exhibiting lines of very high intensity at 8.4 and 17;
- lines of high intensity at 9.9, 10.6, 11.4, 17.5, 19.1, 20.2;
- lines of medium intensity at 4.6, 4.9, 7.1, 12.7, 13.2, 13.6, 15.3, 15.8, 16.4, 16.7, 18.4, 19.7, 21.7, 23.4;
- and lines of weak intensity at 7.8, 8.8, 9.4, 12, 14.1, 14.6, 21, 22.3, 22.8, 23.9, 24.7, 25.3, 25.5, 26.4, 27, 27.7, 28.4 and a relative absolute configuration of the three stereo axes of the dibenzo[d,f][1,3,2]dioxaphosphepin rings of R*,R*,S*.
Dependencies are inferred from the claim text.