Used in everything from model planes to passenger planes, superglue is one of the best-known modern glues. The curing process that facilitates its remarkable (convert from liquid to solid) in the presence of adhesive properties is a chain polymerization reaction. The ingredient that gives superglue its adhesive ability is methyl cyanoacrylate. This compound is just one member of a larger family of cyanoacrylates with the following structure. Contrary to popular understanding, superglue does not"air dry."In fact, cyanoacrylates cure weak nucleophiles such as water. Under normal circumstances, a thin layer of water is present on almost all surfaces. The curing process, therefore, involves the reaction shown here. C=N C=N C=N C=N H,C=C H,O:+ H,C=C? H,O-CH,-C: + H,C= C=0 C=0 ČO,R C=0 R a cyanoacrylate R C=N C=N C=N - Hö-CH,- -C+H etc. HO-CH,-C-CH,-C: +H CO,R COOR ČOOR
Used in everything from model planes to passenger planes, superglue is one of the best-known modern glues. The curing process that facilitates its remarkable (convert from liquid to solid) in the presence of adhesive properties is a chain polymerization reaction. The ingredient that gives superglue its adhesive ability is methyl cyanoacrylate. This compound is just one member of a larger family of cyanoacrylates with the following structure. Contrary to popular understanding, superglue does not"air dry."In fact, cyanoacrylates cure weak nucleophiles such as water. Under normal circumstances, a thin layer of water is present on almost all surfaces. The curing process, therefore, involves the reaction shown here. C=N C=N C=N C=N H,C=C H,O:+ H,C=C? H,O-CH,-C: + H,C= C=0 C=0 ČO,R C=0 R a cyanoacrylate R C=N C=N C=N - Hö-CH,- -C+H etc. HO-CH,-C-CH,-C: +H CO,R COOR ČOOR
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Why does the weak nucleophile, water, efficiently add to the cyanoacrylate?
1. Superglue must possess hydroxide as a promoter to initiate the
2. The carbanion formed by nucleophilic addition of water is resonance-stabilized by two electron-withdrawing groups.
3. The zwitterion formed by addition of water is well solvated in the cyanoacrylate matrix of the glue.
4. Both 1 and 2.
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