Skip to main content
SpringerLink
Log in

Functional polymers. XII: Synthesis and polymerization of 2(2-vinyl-4-hydroxyphenyl)2H-benzotriazole and 2(3-vinyl-4-hydroxyphenyl)2H-benzotriazole

Funktionelle Polymere, XII: Synthese und Polymerisation von 2(2-Vinyl-hydroxyphenyl)2H-benzotriazol und 2(3-Vinyl-4-hydroxyphenyl)2H-benzotriazol

  • Organische Chemie Und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

Condensation of diazotizedo-nitroaniline with 3-ethylphenol or with 2-ethylphenol followed by reduction of the resulting azo compound with zinc dust in sodium hydroxide solution gave 2-(2-ethyl-4-hydroxyphenyl)2H-benzotriazole and 2(3-ethyl-4-hydroxyphenyl)2H-benzotriazole, respectively. The individual compounds were acetylated, brominated withN-bromosuccinimide to the corresponding 1-bromoethyl compounds which were then dehydrobrominated with triethyl amine in acetonitrile and hydrolyzed to 2(2-vinyl-4-hydroxyphenyl)2H-benzotriazole or 2(3-vinyl-4-hydroxyphenyl)2H-benzotriazole. The two monomers could be polymerized and copolymerized with styrene and methyl methacrylate. The ethyl as well as the vinyl compounds and the corresponding polymers, when tested, are ineffective as ultraviolet absorbers as they have structures of 4-hydroxyphenyl rather than 2-hydroxyphenyl compounds with respect to the benzotriazole ring. A careful NMR analysis for the correct structural assignment is also described.

Zusammenfassung

Diazotierteso-Nitroanilin wurde mit 3-Ethylphenol bzw. mit 2-Ethylphenol kondensiert. Reduktion der Diazoverbindung mit Zinkstaub in Natriumhydroxid ergab 2-(2-Ethyl-4-hydroylphenyl)2H-benzotriazol, bzw. 2-(3-Ethyl-4-hydroxyphenyl)2H-benzotriazol. Nach Acetylierung der freien Phenolgruppe wurden diese Verbindungen mitN-Bromsuccinimid zu den entsprechenden1-Bromethylverbindungen umgewandelt und daraufhin in Acetonitril mit Triethylamin dehydrobromiert. Darauf folgende Hydrolyse führte zu 2(2-Vinyl-4-hydroxyphenyl)2H-benzotriazol bzw. zu 2(3-Vinyl-4-hydroxyphenyl)2H-benzotriazol. Beide monomeren Verbindungen wurden sowohl homopolymerisiert als auch mit Styrol oder mit Methylmethacrylat copolymerisiert. Weder die Ethyl- noch die Vinylverbindungen oder deren Polymere erwiesen sich als UV-Stabilisatoren, eine Eigenschaft die den 2(2-Hydroxyphenyl)2H-Benzotriazolen eigen ist. Eine Methode der Strukturbestimmung mit Hilfe einer detaillierten NMR-Analyse wird ebenfalls beschrieben.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Bailey D., Vogl O., J. Macromol. Sci., Reviews,C 14, 267 (1976).

    Google Scholar 

  2. Tirrell D., Bailey D., Vogl O., Polymer Preprints, ACS Division of Polymer Chemistry18, 542 (1977).

    Google Scholar 

  3. Tirrell D., Bailey D., Vogl O., in: Polymeric Drugs (Donaruma L. G., Vogl O., eds.), p. 77. New York: Academic Press. 1978.

    Google Scholar 

  4. Vogl O., Yoshida S., Preprints, Society of Polymer Science, Japan29, 648 (1980).

    Google Scholar 

  5. Vogl O., Yoshida S., Rev. Roum. de Chimie25, 1128 (1980).

    Google Scholar 

  6. Heublein G., Heublein B., Heyroth B., Bendel E., Z. Chem.19, 104 (1979).

    Google Scholar 

  7. Hartmann M., Riedel B., Wondraczek H., Geschwend G., Z. Chem.18, 95 (1978).

    Google Scholar 

  8. Iwasaki M., Tirrell D., Vogl O., J. Polym. Sci., Polym. Chem. Ed.18, 2755 (1980).

    Google Scholar 

  9. Tirrell D., Vogl O., Makromol. Chem.181, 2097 (1980).

    Google Scholar 

  10. Bailey D., Tirrell D., Vogl O., J. Polym. Sci., Polym. Chem. Ed.14, 2725 (1976).

    Google Scholar 

  11. Tirrell D., Bailey D., Pinazzi C., Vogl O., Macromolecules11, 313 (1978).

    Google Scholar 

  12. Sumida Y.,Vogl O., Polymer J. (Japan), in press.

  13. Sumida Y., Yoshida S., Vogl O., Polymer Preprints, ACS Division of Polymer Chemistry21, 201 (1980).

    Google Scholar 

  14. Yoshida S., Vogl O., Polymer Preprints, ACS Division of Polymer Chemistry21, 203 (1980).

    Google Scholar 

  15. Yoshida S.,Vogl O., Makromolekulare Chemie, in press.

  16. Begtrup M., Acta Chem. Scand.27, 3101 (1973).

    Google Scholar 

  17. See also:Ewing D. F., Org. Mag. Resonance12, 499 (1979).

    Google Scholar 

  18. Begtrup M.,Claramunt R. M.,Elgeno J., J. Chem. Soc., Perkin II1978, 99.

  19. Yoshida S.,Lillya C. P.,Vogl O., J. Polym. Sci., Polym. Chem., in press.

Download references

Author information

Authors and Affiliations

  1. Polymer Science and Engineering Department, University of Massachusetts, 01003, Amherst, MA, USA

    Shohei Yoshida, C. Peter Lillya & Otto Vogl

  2. Department of Chemistry, University of Massachusetts, 01003, Amherst, MA, USA

    C. Peter Lillya

Authors
  1. Shohei Yoshida
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. C. Peter Lillya
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Otto Vogl
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

This paper is dedicated to ProfessorGeorge Butler on the occasion of his 65th birthday, with best personal wishes.

Part XI:S. Yoshida andO. Vogl, Makromol. Chem., in press.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yoshida, S., Lillya, C.P. & Vogl, O. Functional polymers. XII: Synthesis and polymerization of 2(2-vinyl-4-hydroxyphenyl)2H-benzotriazole and 2(3-vinyl-4-hydroxyphenyl)2H-benzotriazole. Monatsh Chem 113, 603–622 (1982). https://doi.org/10.1007/BF00800267

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00800267

Keywords

Search

Navigation