Phosphazene High Polymers with Steroidal Side Groups

Harry R. Allcock, T. J. Fuller

Research output: Contribution to journalArticle

55 Citations (Scopus)

Abstract

Steroidal residues derived from desoxoestrone (III), estrone (IV), 17β-estradiol (V), 17α-ethynylestradiol (VI), estradiol 3-methyl ether (VII), and 1,4-dihydroestradiol 3-methyl ether (VIII) have been linked to a polyphosphazene chain via the sodium salt of the steroidal hydroxy function. The degree of replacement of P-Cl bonds by P-OR units was in the range 0.5-40%, depending on the reaction conditions. The residual chlorine atoms were removed by reaction with methylamine, ethyl glycinate, or n-butylamine. Stable polymers of structure XIV were obtained when the steroidal units were linked to phosphorus through an aryloxy residue. However, linkage through an alkoxy residue led to instability and chain cleavage. The use of ethyl glycinato residues as cosubstituent groups yielded hydrolytically degradable polymers. Comparisons are made between these high-polymeric reactions and those of small-molecule cyclophosphazene models.

Original languageEnglish (US)
Pages (from-to)1338-1345
Number of pages8
JournalMacromolecules
Volume13
Issue number6
DOIs
StatePublished - Jan 1 1980

Fingerprint

Methyl Ethers
Ethers
Polymers
Estrone
Chlorine
Phosphorus
Estradiol
Salts
Sodium
Atoms
Molecules
alkoxyl radical
glycine ethyl ester
n-butylamine
17 alpha-iodovinylestradiol
methylamine
poly(phosphazene)

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

Allcock, Harry R. ; Fuller, T. J. / Phosphazene High Polymers with Steroidal Side Groups. In: Macromolecules. 1980 ; Vol. 13, No. 6. pp. 1338-1345.
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Phosphazene High Polymers with Steroidal Side Groups. / Allcock, Harry R.; Fuller, T. J.

In: Macromolecules, Vol. 13, No. 6, 01.01.1980, p. 1338-1345.

Research output: Contribution to journalArticle

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AU - Allcock, Harry R.

AU - Fuller, T. J.

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AB - Steroidal residues derived from desoxoestrone (III), estrone (IV), 17β-estradiol (V), 17α-ethynylestradiol (VI), estradiol 3-methyl ether (VII), and 1,4-dihydroestradiol 3-methyl ether (VIII) have been linked to a polyphosphazene chain via the sodium salt of the steroidal hydroxy function. The degree of replacement of P-Cl bonds by P-OR units was in the range 0.5-40%, depending on the reaction conditions. The residual chlorine atoms were removed by reaction with methylamine, ethyl glycinate, or n-butylamine. Stable polymers of structure XIV were obtained when the steroidal units were linked to phosphorus through an aryloxy residue. However, linkage through an alkoxy residue led to instability and chain cleavage. The use of ethyl glycinato residues as cosubstituent groups yielded hydrolytically degradable polymers. Comparisons are made between these high-polymeric reactions and those of small-molecule cyclophosphazene models.

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