Click chemistry in materials synthesis. III. Metal-adhesive polymers from Cu(I)-catalyzed azide-alkyne cycloaddition

Yi Liu, David D. Díaz, Adrian A. Accurso, K. Barry Sharpless, Valery V. Fokin, M. G. Finn

Research output: Contribution to journalArticle

84 Citations (Scopus)

Abstract

1,2,3-Triazole-based polymers generated from the Cu(I)-catalyzed cycloaddition between multivalent azides and acetylenes are effective adhesive materials for metal surfaces. The adhesive capacities of candidate mixtures of azide and alkyne components were measured by a modified peel test, using a customized adhesive tester. A particularly effective tetravalent alkyne and trivalent azide combination was identified, giving exceptional strength that matches or exceeds the best commercial formulations. The addition of Cu catalyst was found to be important for the synthesis of stronger adhesive polymers when cured at room temperature. Heating also accelerated curing rates, but the maximum adhesive strengths achieved at both room temperature and high temperature were the same, suggesting that crosslinking reaches the same advanced point in all cases. Polytriazoles also form adhesives to aluminum, but copper is bound more effectively, presumably because active Cu(I) ions may be leached from the surface to promote crosslinking and adhesion.

Original languageEnglish
Pages (from-to)5182-5189
Number of pages8
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume45
Issue number22
DOIs
Publication statusPublished - 15 Nov 2007
Externally publishedYes

Fingerprint

Alkynes
Azides
Cycloaddition
Adhesives
Polymers
Metals
Crosslinking
Triazoles
Acetylene
Aluminum
Temperature
Curing
Copper
Adhesion
Ions
Heating
Catalysts

Keywords

  • Adhesives
  • Alkynes
  • Azides
  • Click chemistry
  • Copper
  • Crosslinking
  • Cycloaddition
  • Functionalization of polymers

ASJC Scopus subject areas

  • Polymers and Plastics
  • Materials Chemistry

Cite this

Click chemistry in materials synthesis. III. Metal-adhesive polymers from Cu(I)-catalyzed azide-alkyne cycloaddition. / Liu, Yi; Díaz, David D.; Accurso, Adrian A.; Sharpless, K. Barry; Fokin, Valery V.; Finn, M. G.

In: Journal of Polymer Science, Part A: Polymer Chemistry, Vol. 45, No. 22, 15.11.2007, p. 5182-5189.

Research output: Contribution to journalArticle

Liu, Yi ; Díaz, David D. ; Accurso, Adrian A. ; Sharpless, K. Barry ; Fokin, Valery V. ; Finn, M. G. / Click chemistry in materials synthesis. III. Metal-adhesive polymers from Cu(I)-catalyzed azide-alkyne cycloaddition. In: Journal of Polymer Science, Part A: Polymer Chemistry. 2007 ; Vol. 45, No. 22. pp. 5182-5189.
@article{857fc63e0d444e769fe13f0234a3b2c4,
title = "Click chemistry in materials synthesis. III. Metal-adhesive polymers from Cu(I)-catalyzed azide-alkyne cycloaddition",
abstract = "1,2,3-Triazole-based polymers generated from the Cu(I)-catalyzed cycloaddition between multivalent azides and acetylenes are effective adhesive materials for metal surfaces. The adhesive capacities of candidate mixtures of azide and alkyne components were measured by a modified peel test, using a customized adhesive tester. A particularly effective tetravalent alkyne and trivalent azide combination was identified, giving exceptional strength that matches or exceeds the best commercial formulations. The addition of Cu catalyst was found to be important for the synthesis of stronger adhesive polymers when cured at room temperature. Heating also accelerated curing rates, but the maximum adhesive strengths achieved at both room temperature and high temperature were the same, suggesting that crosslinking reaches the same advanced point in all cases. Polytriazoles also form adhesives to aluminum, but copper is bound more effectively, presumably because active Cu(I) ions may be leached from the surface to promote crosslinking and adhesion.",
keywords = "Adhesives, Alkynes, Azides, Click chemistry, Copper, Crosslinking, Cycloaddition, Functionalization of polymers",
author = "Yi Liu and D{\'i}az, {David D.} and Accurso, {Adrian A.} and Sharpless, {K. Barry} and Fokin, {Valery V.} and Finn, {M. G.}",
year = "2007",
month = "11",
day = "15",
doi = "10.1002/pola.22262",
language = "English",
volume = "45",
pages = "5182--5189",
journal = "Journal of Polymer Science, Part A: Polymer Chemistry",
issn = "0887-624X",
publisher = "John Wiley and Sons Inc.",
number = "22",

}

TY - JOUR

T1 - Click chemistry in materials synthesis. III. Metal-adhesive polymers from Cu(I)-catalyzed azide-alkyne cycloaddition

AU - Liu, Yi

AU - Díaz, David D.

AU - Accurso, Adrian A.

AU - Sharpless, K. Barry

AU - Fokin, Valery V.

AU - Finn, M. G.

PY - 2007/11/15

Y1 - 2007/11/15

N2 - 1,2,3-Triazole-based polymers generated from the Cu(I)-catalyzed cycloaddition between multivalent azides and acetylenes are effective adhesive materials for metal surfaces. The adhesive capacities of candidate mixtures of azide and alkyne components were measured by a modified peel test, using a customized adhesive tester. A particularly effective tetravalent alkyne and trivalent azide combination was identified, giving exceptional strength that matches or exceeds the best commercial formulations. The addition of Cu catalyst was found to be important for the synthesis of stronger adhesive polymers when cured at room temperature. Heating also accelerated curing rates, but the maximum adhesive strengths achieved at both room temperature and high temperature were the same, suggesting that crosslinking reaches the same advanced point in all cases. Polytriazoles also form adhesives to aluminum, but copper is bound more effectively, presumably because active Cu(I) ions may be leached from the surface to promote crosslinking and adhesion.

AB - 1,2,3-Triazole-based polymers generated from the Cu(I)-catalyzed cycloaddition between multivalent azides and acetylenes are effective adhesive materials for metal surfaces. The adhesive capacities of candidate mixtures of azide and alkyne components were measured by a modified peel test, using a customized adhesive tester. A particularly effective tetravalent alkyne and trivalent azide combination was identified, giving exceptional strength that matches or exceeds the best commercial formulations. The addition of Cu catalyst was found to be important for the synthesis of stronger adhesive polymers when cured at room temperature. Heating also accelerated curing rates, but the maximum adhesive strengths achieved at both room temperature and high temperature were the same, suggesting that crosslinking reaches the same advanced point in all cases. Polytriazoles also form adhesives to aluminum, but copper is bound more effectively, presumably because active Cu(I) ions may be leached from the surface to promote crosslinking and adhesion.

KW - Adhesives

KW - Alkynes

KW - Azides

KW - Click chemistry

KW - Copper

KW - Crosslinking

KW - Cycloaddition

KW - Functionalization of polymers

UR - http://www.scopus.com/inward/record.url?scp=35748974234&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=35748974234&partnerID=8YFLogxK

U2 - 10.1002/pola.22262

DO - 10.1002/pola.22262

M3 - Article

VL - 45

SP - 5182

EP - 5189

JO - Journal of Polymer Science, Part A: Polymer Chemistry

JF - Journal of Polymer Science, Part A: Polymer Chemistry

SN - 0887-624X

IS - 22

ER -