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Chapter 22: Problem 86

Polyesters containing double bonds are often crosslinked by reacting the polymer with styrene. a. Draw the structure of the copolymer of $\mathrm{HO}-\mathrm{CH}_{2} \mathrm{CH}_{2}-\mathrm{OH} \quad\( and \)\quad \mathrm{HO}_{2} \mathrm{C}-\mathrm{CH}=\mathrm{CH}-\mathrm{CO}_{2} \mathrm{H}$ b. Draw the structure of the crosslinked polymer (after the polyester has been reacted with styrene).

Short Answer

Expert verified
The copolymer structure of \(\mathrm{HO}-\mathrm{CH}_{2}\mathrm{CH}_{2}-\mathrm{OH}\) and \(\mathrm{HO}_{2}\mathrm{C}-\mathrm{CH}=\mathrm{CH}-\mathrm{CO}_{2}\mathrm{H}\) is: \(\mathrm{CH}_{2}\mathrm{CH}_{2}-\mathrm{OOC}-\mathrm{CH}=\mathrm{CH}-\mathrm{COO}-\mathrm{CH}_{2}\mathrm{CH}_{2}\). After reacting with styrene, the crosslinked polymer structure becomes: \(\mathrm{CH}_{2}\mathrm{CH}_{2}-\mathrm{OOC}-\mathrm{CH}-\mathrm{CH}(\mathrm{Ph})-\mathrm{COO}-\mathrm{CH}_{2}\mathrm{CH}_{2}\).

Step by step solution

01

Identifying Reaction Sites for Copolymer Formation

First, identify the reactive functional groups on both monomers. In the case of the diol (\(\mathrm{HO}-\mathrm{CH}_{2}\mathrm{CH}_{2}-\mathrm{OH}\)), the hydroxyl groups at each end will react, while in the diacid (\(\mathrm{HO}_{2}\mathrm{C}-\mathrm{CH}=\mathrm{CH}-\mathrm{CO}_{2}\mathrm{H}\)), the carboxyl groups will react.
02

Drawing Copolymer Structure

Create a copolymer by reacting the hydroxyl groups of the diol with the carboxyl groups of the diacid. This reaction forms an ester linkage as follows: \(\mathrm{HO}-\mathrm{CH}_{2}\mathrm{CH}_{2}-\mathrm{OH}\) + \(\mathrm{HO}_{2}\mathrm{C}-\mathrm{CH}=\mathrm{CH}-\mathrm{CO}_{2}\mathrm{H}\) -> \(\mathrm{CH}_{2}\mathrm{CH}_{2}-\mathrm{OOC}-\mathrm{CH}=\mathrm{CH}-\mathrm{COO}-\mathrm{CH}_{2}\mathrm{CH}_{2}\)
03

Identifying Reaction Sites for Crosslinking

The next step is to analyze the structure of the copolymer and identify areas that possibly react with the styrene (\(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{Ph}\)). The double bond in the diacid part of our copolymer will participate in the crosslinking reaction.
04

Drawing Crosslinked Polymer Structure

React the copolymer with styrene to create the crosslinked polymer. The double bond in the diacid part of the copolymer reacts with the double bond of the styrene molecule, forming a new single bond and connecting the copolymer and styrene. The crosslinked polymer structure will look like this: \(\mathrm{CH}_{2}\mathrm{CH}_{2}-\mathrm{OOC}-\mathrm{CH}-\mathrm{CH}-\mathrm{COO}-\mathrm{CH}_{2}\mathrm{CH}_{2} + \mathrm{CH}_{2}=\mathrm{CH}-\mathrm{Ph}\) -> \(\mathrm{CH}_{2}\mathrm{CH}_{2}-\mathrm{OOC}-\mathrm{CH}-\mathrm{CH}(\mathrm{Ph})-\mathrm{COO}-\mathrm{CH}_{2}\mathrm{CH}_{2}\)

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