Synthesis of Polyphosphazenes with Isothiocyanato, Thiourethane, and Thiourea Side Groups

Harry R. Allcock, J. Steven Rutt

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The isothiocyanatophosphazene, [NP(NCS)2]3, undergoes ring-opening polymerization when heated at temperatures above 100 °C to form a low molecular weight polymer, [NP(NCS)2]n. The copolymerization of [NP(NCS)2]3 and [NP(NCS)2]3 was examined, and mechanistic implications for cyclophospha-zene polymerization are discussed. High molecular weight [NP(NCS)2]n was prepared by the metathetical exchange reaction of (NPCl2)n with potassium thiocyanate. Treatment of [NP(NCS)2]n with alcohols and amines to form thiourethane and thiourea derivatives was examined. Steric and electronic effects prevented full reaction of the isothiocyanato side groups with alcohols. However, thiourea derivatives, [NP-(NHCSNHR)2]n, were prepared by the reactions of [NP(NCS)2]n with amines. Mixed-substituent thiourethane and thiourea phosphazene polymers with trifluoroethoxy or 2-(2-methoxyethoxy)ethoxy cosubstituent groups were also synthesized. The characterization and properties of the thiourethane and thiourea phosphazene polymers are described.

Original languageEnglish (US)
Pages (from-to)2852-2857
Number of pages6
JournalMacromolecules
Volume24
Issue number10
DOIs
StatePublished - May 1 1991

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Thiourea
Thioureas
Polymers
Amines
Alcohols
Molecular weight
Derivatives
Ring opening polymerization
Copolymerization
Potassium
Polymerization
Temperature

All Science Journal Classification (ASJC) codes

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

Cite this

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title = "Synthesis of Polyphosphazenes with Isothiocyanato, Thiourethane, and Thiourea Side Groups",
abstract = "The isothiocyanatophosphazene, [NP(NCS)2]3, undergoes ring-opening polymerization when heated at temperatures above 100 °C to form a low molecular weight polymer, [NP(NCS)2]n. The copolymerization of [NP(NCS)2]3 and [NP(NCS)2]3 was examined, and mechanistic implications for cyclophospha-zene polymerization are discussed. High molecular weight [NP(NCS)2]n was prepared by the metathetical exchange reaction of (NPCl2)n with potassium thiocyanate. Treatment of [NP(NCS)2]n with alcohols and amines to form thiourethane and thiourea derivatives was examined. Steric and electronic effects prevented full reaction of the isothiocyanato side groups with alcohols. However, thiourea derivatives, [NP-(NHCSNHR)2]n, were prepared by the reactions of [NP(NCS)2]n with amines. Mixed-substituent thiourethane and thiourea phosphazene polymers with trifluoroethoxy or 2-(2-methoxyethoxy)ethoxy cosubstituent groups were also synthesized. The characterization and properties of the thiourethane and thiourea phosphazene polymers are described.",
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Synthesis of Polyphosphazenes with Isothiocyanato, Thiourethane, and Thiourea Side Groups. / Allcock, Harry R.; Steven Rutt, J.

In: Macromolecules, Vol. 24, No. 10, 01.05.1991, p. 2852-2857.

Research output: Contribution to journalArticle

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N2 - The isothiocyanatophosphazene, [NP(NCS)2]3, undergoes ring-opening polymerization when heated at temperatures above 100 °C to form a low molecular weight polymer, [NP(NCS)2]n. The copolymerization of [NP(NCS)2]3 and [NP(NCS)2]3 was examined, and mechanistic implications for cyclophospha-zene polymerization are discussed. High molecular weight [NP(NCS)2]n was prepared by the metathetical exchange reaction of (NPCl2)n with potassium thiocyanate. Treatment of [NP(NCS)2]n with alcohols and amines to form thiourethane and thiourea derivatives was examined. Steric and electronic effects prevented full reaction of the isothiocyanato side groups with alcohols. However, thiourea derivatives, [NP-(NHCSNHR)2]n, were prepared by the reactions of [NP(NCS)2]n with amines. Mixed-substituent thiourethane and thiourea phosphazene polymers with trifluoroethoxy or 2-(2-methoxyethoxy)ethoxy cosubstituent groups were also synthesized. The characterization and properties of the thiourethane and thiourea phosphazene polymers are described.

AB - The isothiocyanatophosphazene, [NP(NCS)2]3, undergoes ring-opening polymerization when heated at temperatures above 100 °C to form a low molecular weight polymer, [NP(NCS)2]n. The copolymerization of [NP(NCS)2]3 and [NP(NCS)2]3 was examined, and mechanistic implications for cyclophospha-zene polymerization are discussed. High molecular weight [NP(NCS)2]n was prepared by the metathetical exchange reaction of (NPCl2)n with potassium thiocyanate. Treatment of [NP(NCS)2]n with alcohols and amines to form thiourethane and thiourea derivatives was examined. Steric and electronic effects prevented full reaction of the isothiocyanato side groups with alcohols. However, thiourea derivatives, [NP-(NHCSNHR)2]n, were prepared by the reactions of [NP(NCS)2]n with amines. Mixed-substituent thiourethane and thiourea phosphazene polymers with trifluoroethoxy or 2-(2-methoxyethoxy)ethoxy cosubstituent groups were also synthesized. The characterization and properties of the thiourethane and thiourea phosphazene polymers are described.

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