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New method for the synthesis of fully aliphatic telechelic α,ω-dihydroxy-polyisobutylene

Publication ,  Journal Article
Castano, M; Becker, ML; Puskas, JE
Published in: Polymer Chemistry
September 21, 2014

This paper reports a new method for the synthesis of α,ω- primary-dihydroxy PIBs (HO-PIB-OH) with a fully aliphatic backbone. Three aliphatic difunctional initiators with tertiary-methoxy, tertiary-chloride and tertiary-hydroxyl end groups (TMHDiOMe, TMHDiCl and TMHDiOH) were screened in conjunction with TiCl4 and DMA in a solution system (hexane-CH 3Cl, 60/40, v/v). TMHDiOMe yielded only traces of PIB, while TMHDiOH and TMHDiCl yielded PIBs with a mixture of end group structures. The same initiators were also screened in heterogeneous systems (CH3Cl or CH2Cl2). TMHDiOMe/TiCl4 yielded no polymer in either diluent, CH3Cl, and TMHDiOH/TiCl4 led to olefinic end groups. While TMHDiCl/TiCl4 resulted in clean Cl-PIB-Cl in CH3Cl, the Ieff values were low and TMHDiCl was very unstable and difficult to isolate. Premixing TMHDiOH with TiCl4 in CH3Cl led to the in situ formation of TMHDiCl. Addition of hexane and IB, followed by end-capping with allyltrimethylsilane resulted in the formation of allyl-PIB-allyl. Click chemistry with HS-CH2-CH2-OH yielded α,ω-primary-dihydroxy-PIB (HO-PIB-OH) with Mn = 4085 g mol-1 and M = 1.2. 1H-NMR analysis verified the structure of the HO-PIB-OH. © 2014 the Partner Organisations.

Duke Scholars

Published In

Polymer Chemistry

DOI

EISSN

1759-9962

ISSN

1759-9954

Publication Date

September 21, 2014

Volume

5

Issue

18

Start / End Page

5436 / 5442

Related Subject Headings

  • 4018 Nanotechnology
  • 3406 Physical chemistry
  • 3403 Macromolecular and materials chemistry
  • 0307 Theoretical and Computational Chemistry
  • 0303 Macromolecular and Materials Chemistry
 

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Castano, M., Becker, M. L., & Puskas, J. E. (2014). New method for the synthesis of fully aliphatic telechelic α,ω-dihydroxy-polyisobutylene. Polymer Chemistry, 5(18), 5436–5442. https://doi.org/10.1039/c4py00569d
Castano, M., M. L. Becker, and J. E. Puskas. “New method for the synthesis of fully aliphatic telechelic α,ω-dihydroxy-polyisobutylene.” Polymer Chemistry 5, no. 18 (September 21, 2014): 5436–42. https://doi.org/10.1039/c4py00569d.
Castano M, Becker ML, Puskas JE. New method for the synthesis of fully aliphatic telechelic α,ω-dihydroxy-polyisobutylene. Polymer Chemistry. 2014 Sep 21;5(18):5436–42.
Castano, M., et al. “New method for the synthesis of fully aliphatic telechelic α,ω-dihydroxy-polyisobutylene.” Polymer Chemistry, vol. 5, no. 18, Sept. 2014, pp. 5436–42. Scopus, doi:10.1039/c4py00569d.
Castano M, Becker ML, Puskas JE. New method for the synthesis of fully aliphatic telechelic α,ω-dihydroxy-polyisobutylene. Polymer Chemistry. 2014 Sep 21;5(18):5436–5442.
Journal cover image

Published In

Polymer Chemistry

DOI

EISSN

1759-9962

ISSN

1759-9954

Publication Date

September 21, 2014

Volume

5

Issue

18

Start / End Page

5436 / 5442

Related Subject Headings

  • 4018 Nanotechnology
  • 3406 Physical chemistry
  • 3403 Macromolecular and materials chemistry
  • 0307 Theoretical and Computational Chemistry
  • 0303 Macromolecular and Materials Chemistry