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
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
Why does the weak nucleophile, water, efficiently add to the cyanoacrylate?
1. Superglue must possess hydroxide as a promoter to initiate the polymerization in the presence of water.
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.
Transcribed Image Text: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
Definition Definition Chemical process in which one or more monomers combine to produce a very large chain-like molecule called a polymer. The functional groups present on the monomers and their steric effects are responsible for polymerization through a sequence of reactions that vary in complexity. There exists a stable covalent chemical bond between monomers that sets apart polymerization from other processes.
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