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Derivatives of phosphonated polypropylene

Z. Maňásek, D. Belluš, and B. Böhmer

Slovak Academy of Sciences, Bratislava


Abstract: Atactic polypropylene (I) was chlorophosphonated with PCl3 and O (Schroeder and Sopchak, CA 55, 12913h) to form a polymer (II) (0.17 mole P introduced per 100 g.), and the reactive POCl2 groups were esterified to the extent of 70-85% by reaction with Na alcoholates. The Me and allyl esters that were prepd. have the same appearance as hydrolyzed II. The dodecyl esters possess good plasticity, and the di- and polyhydroxy compds. yield branched products of II with good thermomech. properties. By treating II with alcs., in the presence of tertiary amines for trapping the liberated HCl, products of a lower degree of esterification are obtained. Amidation of II to the extent of 90% yielded brittle derivs., insol. in org. solvents. By treating cellulose, previously wet with pyridine, with a 2% soln. of II in xylene for 48 hrs. at 30°, a stiff and impermeable deriv. was obtained after extn. of the excess II with Et2O. Hydroxyethyl cellulose reacted in a similar way. It is presumed that a thin superficial layer of branched polymer is formed through the formation of phosphonate groups. Isotactic I (threads or film) was chlorophosphonated to form a polymer (III) by repeated immersions into PCl3 followed by exposure to O, or alternatively by previously ozonizing I (0.22 mole O3/l. O at 21° for 4 hrs.), immersing it in PCl3, and then exposing it at 60° in N. More intensive phosphonation resulted in the destruction of I (min. mech. stability preserved with 0.63% P). Hydrolyzed III has a greater capacity to adsorb moisture and dyes. Stabilizers, such as 2,2'-dihydroxy-4-methoxybenzophenone or 2,2'-methylenebis(4-methyl-6-tert-butyl)phenol, or their mixts., were fixed on I to form a polymer (IV) by treating III with a soln. of stabilizer and PhNEt2 in xylene and then exposing for 1 hr. in N at 115°. Hydrolyzed III, and esp. IV, show, as compared to I, excellent stability towards O at 150°, as well as towards ultraviolet radiation, in regard to their mech. properties. Only extn. of IV for 10 hrs. with Me2CO decreased its stability to any considerable extent.

Full paper in Portable Document Format: 175a318.pdf (in Slovak)


Chemical Papers 17 (5) 318–329 (1963)

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