Amine, melamine, and amide n -halamines as antimicrobial additives for polymers

Xinbo Sun, Zhengbing Cao, Nuala Porteous, Yuyu Sun

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

N-Chloro-2,2,6,6-tetramethyl-4-piperidinol laurate (Cl-TMPL) was prepared by reacting 2,2,6,6-tetramethyl-4-piperidinol hydrochloride (TMP·HCl) with lauroyl chloride, followed by chlorination with sodium dichloroisocyanurate. The chemical structure of Cl-TMPL was characterized with FT-IR, NMR, DSC, and TGA analyses. The antimicrobial performance of Cl-TMPL against Gram-positive and Gram-negative bacteria was compared with 1-chloro-3-dodecyl-5,5-dimethylhydantoin (Cl-DDMH), an amide N-halamine, and chloro-2,4-diamino-6-dodecyl-1,3,5-triazine (Cl-DADT), a melamine (imino) N-halamine. The three classes of N-halamines were used as additives for polyurethane (PU). Visible light transparency data indicated that up to 6% of Cl-DDMH or Cl-DADT could be compatibly mixed with PU, but Cl-TMPL had low compatibility with PU at higher than 2% of Cl-TMPL. With the same additive content, Cl-DDMH and Cl-DADT provided more powerful antimicrobial and biofilm-controlling effects than Cl-TMPL. In stability studies, however, PU samples with Cl-TMPL released the lowest amount of active chlorine into the immersing solution, suggesting the highest stability of the antimicrobial and biofilm-controlling efficacy.

Original languageEnglish (US)
Pages (from-to)11206-11213
Number of pages8
JournalIndustrial and Engineering Chemistry Research
Volume49
Issue number22
DOIs
StatePublished - Nov 17 2010

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Laurates
Melamine
Amides
Polyurethanes
Amines
Polymers
Biofilms
Triazines
Chlorination
Transparency
Chlorine
Bacteria
Sodium
Nuclear magnetic resonance
lastar A
melamine
Chlorides

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Chemistry(all)
  • Industrial and Manufacturing Engineering

Cite this

Amine, melamine, and amide n -halamines as antimicrobial additives for polymers. / Sun, Xinbo; Cao, Zhengbing; Porteous, Nuala; Sun, Yuyu.

In: Industrial and Engineering Chemistry Research, Vol. 49, No. 22, 17.11.2010, p. 11206-11213.

Research output: Contribution to journalArticle

Sun, Xinbo ; Cao, Zhengbing ; Porteous, Nuala ; Sun, Yuyu. / Amine, melamine, and amide n -halamines as antimicrobial additives for polymers. In: Industrial and Engineering Chemistry Research. 2010 ; Vol. 49, No. 22. pp. 11206-11213.
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abstract = "N-Chloro-2,2,6,6-tetramethyl-4-piperidinol laurate (Cl-TMPL) was prepared by reacting 2,2,6,6-tetramethyl-4-piperidinol hydrochloride (TMP·HCl) with lauroyl chloride, followed by chlorination with sodium dichloroisocyanurate. The chemical structure of Cl-TMPL was characterized with FT-IR, NMR, DSC, and TGA analyses. The antimicrobial performance of Cl-TMPL against Gram-positive and Gram-negative bacteria was compared with 1-chloro-3-dodecyl-5,5-dimethylhydantoin (Cl-DDMH), an amide N-halamine, and chloro-2,4-diamino-6-dodecyl-1,3,5-triazine (Cl-DADT), a melamine (imino) N-halamine. The three classes of N-halamines were used as additives for polyurethane (PU). Visible light transparency data indicated that up to 6{\%} of Cl-DDMH or Cl-DADT could be compatibly mixed with PU, but Cl-TMPL had low compatibility with PU at higher than 2{\%} of Cl-TMPL. With the same additive content, Cl-DDMH and Cl-DADT provided more powerful antimicrobial and biofilm-controlling effects than Cl-TMPL. In stability studies, however, PU samples with Cl-TMPL released the lowest amount of active chlorine into the immersing solution, suggesting the highest stability of the antimicrobial and biofilm-controlling efficacy.",
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