Difference between revisions of "Team:TU Darmstadt/Project/Chem/Methods"

Line 3: Line 3:
 
<p>&nbsp;</p>
 
<p>&nbsp;</p>
 
<h2>Thermal polyesterification of itaconic acid (IA), polyethylene glycol 400</h2>
 
<h2>Thermal polyesterification of itaconic acid (IA), polyethylene glycol 400</h2>
<p>&nbsp;</p>
 
 
<p>&nbsp;</p>
 
<p>&nbsp;</p>
 
<p>Polymers were prepared in dependence on the experimental procedures of <em>Barrett et al.</em><sup>[1]</sup></p>
 
<p>Polymers were prepared in dependence on the experimental procedures of <em>Barrett et al.</em><sup>[1]</sup></p>
 
<p>The procedure requires exact masses. Therefore an analytical balance (4 decimal places) was used and if not otherwise stated PEG as well as itaconic acid were pre-dried before use on a high vacuum line (&lt; 10<sup>-3</sup> mbar) overnight.</p>
 
<p>The procedure requires exact masses. Therefore an analytical balance (4 decimal places) was used and if not otherwise stated PEG as well as itaconic acid were pre-dried before use on a high vacuum line (&lt; 10<sup>-3</sup> mbar) overnight.</p>
 
<p>To avoid contamination with oxygen during the reaction and to remove produced water, common Schlenk technique was applied. As inert gas argon was used.</p>
 
<p>To avoid contamination with oxygen during the reaction and to remove produced water, common Schlenk technique was applied. As inert gas argon was used.</p>
 +
<p>&nbsp;</p>
 
<p>&nbsp;</p>
 
<p>&nbsp;</p>
 
<h3>A1</h3>
 
<h3>A1</h3>
Line 19: Line 19:
 
<p><em>Analysis:</em></p>
 
<p><em>Analysis:</em></p>
 
<p>No further analyses were performed.</p>
 
<p>No further analyses were performed.</p>
 +
<p>&nbsp;</p>
 
<p>&nbsp;</p>
 
<p>&nbsp;</p>
 
<h3>A2</h3>
 
<h3>A2</h3>
Line 38: Line 39:
 
<html/>
 
<html/>
 
<p>Figure 1: DSC- Plot of A2. The T<sub>g</sub> of A2 is -4.7 &deg;C</p>
 
<p>Figure 1: DSC- Plot of A2. The T<sub>g</sub> of A2 is -4.7 &deg;C</p>
 +
<p>&nbsp;</p>
 
<p>&nbsp;</p>
 
<p>&nbsp;</p>
 
<h3>A3</h3>
 
<h3>A3</h3>
Line 61: Line 63:
 
<p>The product was analyzed by <sup>1</sup>H-NMR to ensure that double bonds are still intact in the product.</p>
 
<p>The product was analyzed by <sup>1</sup>H-NMR to ensure that double bonds are still intact in the product.</p>
 
<p>Figure 3 shows the spectrum with an enlargement of the olefin region.</p>
 
<p>Figure 3 shows the spectrum with an enlargement of the olefin region.</p>
<p>&nbsp;</p>
+
<html>
 +
<img width="750px" heigh="517px" src="https://static.igem.org/mediawiki/2015/7/78/TU_Darmstadt_Chemie_NMR_A3.jpg" alt="NMR A3">
 +
<html/>
 
<p>Figure 3:&nbsp;<sup>1</sup>H-NMR (300 MHz) of A3 in CDCl<sub>3</sub></p>
 
<p>Figure 3:&nbsp;<sup>1</sup>H-NMR (300 MHz) of A3 in CDCl<sub>3</sub></p>
 
<p>&nbsp;</p>
 
<p>&nbsp;</p>
Line 134: Line 138:
 
<p>The product was analyzed by differential scanning calorimetry DSC to identify the glass transition (T<sub>g</sub>) temperature.</p>
 
<p>The product was analyzed by differential scanning calorimetry DSC to identify the glass transition (T<sub>g</sub>) temperature.</p>
 
<p>The T<sub>g</sub> of A3 is -49.1 &deg;C.</p>
 
<p>The T<sub>g</sub> of A3 is -49.1 &deg;C.</p>
 +
<html>
 +
<img width="750px" heigh="517px" src="https://static.igem.org/mediawiki/2015/c/c0/TU_Darmstadt_Chemie_DSC-Plot_A4.jpg" alt="DSC-Plot A4">
 +
<html/>
 
<p>Figure 4: DSC- Plot of A4. The T<sub>g</sub> of A4 is -49.1 &deg;C</p>
 
<p>Figure 4: DSC- Plot of A4. The T<sub>g</sub> of A4 is -49.1 &deg;C</p>
 
<p>&nbsp;</p>
 
<p>&nbsp;</p>
Line 139: Line 146:
 
<p>The product was analyzed by <sup>1</sup>H-NMR to ensure that double bonds are still intact in the product.</p>
 
<p>The product was analyzed by <sup>1</sup>H-NMR to ensure that double bonds are still intact in the product.</p>
 
<p>Figure 5 shows the spectrum with an enlargement of the olefin region.</p>
 
<p>Figure 5 shows the spectrum with an enlargement of the olefin region.</p>
 +
<html>
 +
<img width="750px" heigh="517px" src="https://static.igem.org/mediawiki/2015/3/36/TU_Darmstadt_Chemie_NMR_A4.jpg" alt="NMR A4">
 +
<html/>
 
<p>Figure 5: <sup>1</sup>H-NMR (300 MHz) of A4 in CDCl<sub>3</sub>.</p>
 
<p>Figure 5: <sup>1</sup>H-NMR (300 MHz) of A4 in CDCl<sub>3</sub>.</p>
 +
<p>&nbsp;</p>
 +
<p>&nbsp;</p>
 +
<h3>A10</h3>
 +
<p><em>Date: </em>16/07/15 &ndash; 17/07/15</p>
 +
<p><em>Lab members: </em>FR, AW</p>
 +
<p>&nbsp;</p>
 +
<p><em>Preparation process:</em></p>
 +
<p>A 20 mL snap-cap vial was loaded with 2.2750g (5.688 mmol, 1 eq.) PEG-400, 0.7388 g (5.679&nbsp;mmol, 1 eq.) itaconic acid and capped with a pierced aluminium foil. The mixture was heated up to 145 &deg;C with an oil bath on air. No vacuum was applied and the mixture was stirred on air at 145&nbsp;&deg;C for 21 h. The brown-colored viscous liquid was cooled down to room temperature.</p>
 +
<p>&nbsp;</p>
 +
<p><em>Visual Observations:</em></p>
 +
<p>The brown-colored product was more viscous than A8 but less viscous than A7 and A9.</p>
 +
<p>&nbsp;</p>
 +
<p><em>Analysis:</em></p>
 +
<p>DSC</p>
 +
<p>The product was analyzed by differential scanning calorimetry DSC to identify the glass transition (T<sub>g</sub>) temperature.</p>
 +
<p>The T<sub>g</sub> of A10 is -46.9 &deg;C.</p>
 +
<html>
 +
<img width="750px" heigh="517px" src="https://static.igem.org/mediawiki/2015/a/a6/TU_Darmstadt_Chemie_DSC-Plot_A10.jpg" alt="DSC-Plot A10">
 +
<html/>
 +
<p>Figure 6:DSC- Plot of A10. The T<sub>g</sub> of A10 is -46.9 &deg;C.</p>
 +
<p>&nbsp;</p>
 +
<p>&nbsp;</p>
 +
<p>&nbsp;</p>
 +
<h2>Thermal polyesterification of itaconic acid (IA), polyethylene glycol 400 (PEG-400) and xylitol</h2>
 +
<p>&nbsp;</p>
 +
<p>Polymers were prepared in dependence on the experimental procedures of <em>Barrett et al.</em><sup>[1]</sup></p>
 +
<p>The procedure requires exact masses. Therefore an analytical balance (4 decimal places) was used and if not otherwise stated PEG as well as itaconic acid and xylitol were pre-dried before use on a high vacuum line (&lt; 10<sup>-3</sup> mbar) overnight.</p>
 +
<p>&nbsp;</p>
 +
<p>&nbsp;</p>
 +
<h3>A5</h3>
 +
<p><em>Date: </em>30/06/15 &ndash; 01/07/15</p>
 +
<p><em>Lab members: </em>FR, SJ, AW, SZ</p>
 +
<p>&nbsp;</p>
 +
<p><em>Preparation process:</em></p>
 +
<p>A 20 mL snap-cap vial was loaded with 0.997 g (2.491 mmol, 0.43 eq.) PEG-400, 0.3833 g (2.519&nbsp;mmol, 0.44 eq.) xylitol, 0.7503 g (5.767&nbsp;mmol, 1 eq.) itaconic acid and capped with a pierced aluminium foil. The mixture was heated up to 145 &deg;C with an oil bath on air. No vacuum was applied and the mixture was stirred on air at 145 &deg;C for 17.5 h. The orange-colored gel was cooled down to room temperature.</p>
 +
<p>&nbsp;</p>
 +
<p><em>Visual Observations:</em></p>
 +
<p>The orange-colored product was a ductile gel. For a picture of A5 see appendix.</p>
 +
<p>&nbsp;</p>
 +
<p><em>Analysis:</em></p>
 +
<p>Solubility Tests</p>
 +
<table>
 +
<tbody>
 +
<tr>
 +
<td>
 +
<p><strong>Solvent</strong></p>
 +
</td>
 +
<td>
 +
<p><strong>Solubility of Product A5</strong></p>
 +
</td>
 +
</tr>
 +
<tr>
 +
<td>
 +
<p>H<sub>2</sub>O</p>
 +
</td>
 +
<td>
 +
<p>no</p>
 +
</td>
 +
</tr>
 +
<tr>
 +
<td>
 +
<p>THF</p>
 +
</td>
 +
<td>
 +
<p>no</p>
 +
</td>
 +
</tr>
 +
<tr>
 +
<td>
 +
<p>Aceton</p>
 +
</td>
 +
<td>
 +
<p>no</p>
 +
</td>
 +
</tr>
 +
<tr>
 +
<td>
 +
<p>EtOH</p>
 +
</td>
 +
<td>
 +
<p>no</p>
 +
</td>
 +
</tr>
 +
<tr>
 +
<td>
 +
<p>MeOH</p>
 +
</td>
 +
<td>
 +
<p>no</p>
 +
</td>
 +
</tr>
 +
</tbody>
 +
</table>
 +
<p>The gel wasn&rsquo;t soluble in any solvent. Even by applying ultrasound no dissolving occurred. This is probably due to high cross linking with xylitol.</p>
 +
<p>&nbsp;</p>
 +
<p>&nbsp;</p>
 +
<h3>A6</h3>
 +
<p><em>Date: </em>30/06/15 &ndash; 01/07/15</p>
 +
<p><em>Lab members: </em>FR, SJ, AW, SZ</p>
 +
<p>&nbsp;</p>
 +
<p><em>Preparation process:</em></p>
 +
<p>A 20 mL snap-cap vial was loaded with 1.2775 g (3.194 mmol, 0.58 eq.) PEG-400, 0.2038 g (1.339&nbsp;mmol, 0.25 eq.) xylitol, 0.7099 g (5.457&nbsp;mmol, 1 eq.) itaconic acid and capped with a pierced aluminium foil. The mixture was heated up to 145 &deg;C with an oil bath on air. No vacuum was applied and the mixture was stirred on air at 145 &deg;C for 17.5 h. The orange-colored viscous liquid was cooled down to room temperature.</p>
 +
<p>&nbsp;</p>
 +
<p><em>Visual Observations:</em></p>
 +
<p>The orange-colored product was a ductile gel. For a picture of A6 see appendix.</p>
 +
<p>&nbsp;</p>
 +
<p><em>Analysis:</em></p>
 +
<p>Solubility Tests</p>
 +
<table>
 +
<tbody>
 +
<tr>
 +
<td>
 +
<p><strong>Solvent</strong></p>
 +
</td>
 +
<td>
 +
<p><strong>Solubility of Product A6</strong></p>
 +
</td>
 +
</tr>
 +
<tr>
 +
<td>
 +
<p>H<sub>2</sub>O</p>
 +
</td>
 +
<td>
 +
<p>no</p>
 +
</td>
 +
</tr>
 +
<tr>
 +
<td>
 +
<p>THF</p>
 +
</td>
 +
<td>
 +
<p>no</p>
 +
</td>
 +
</tr>
 +
<tr>
 +
<td>
 +
<p>Aceton</p>
 +
</td>
 +
<td>
 +
<p>no</p>
 +
</td>
 +
</tr>
 +
<tr>
 +
<td>
 +
<p>EtOH</p>
 +
</td>
 +
<td>
 +
<p>no</p>
 +
</td>
 +
</tr>
 +
<tr>
 +
<td>
 +
<p>MeOH</p>
 +
</td>
 +
<td>
 +
<p>no</p>
 +
</td>
 +
</tr>
 +
</tbody>
 +
</table>
 +
<p>The gel wasn&rsquo;t soluble in any solvent. Even by applying ultrasound no dissolving occurred. This is probably due to high cross linking with xylitol.</p>
 +
<p>&nbsp;</p>
 +
<p>&nbsp;</p>
 +
<h3>A8&nbsp;</h3>
 +
<p><em>Date: </em>16/07/15 &ndash; 17/07/15</p>
 +
<p><em>Lab members: </em>FR, AW</p>
 +
<p>&nbsp;</p>
 +
<p><em>Preparation process:</em></p>
 +
<p>A 20 mL snap-cap vial was loaded with 3.4567 g (8.642 mmol, 0.90 eq.) PEG-400, 0.0973 g (0.640&nbsp;mmol, 0.067 eq.) xylitol, 1.2492 g (9.602&nbsp;mmol, 1 eq.) itaconic acid and capped with a pierced aluminium foil. The mixture was heated up to 145 &deg;C with an oil bath on air. No vacuum was applied and the mixture was stirred on air at 145 &deg;C for 21 h. The orange-colored viscous liquid was cooled down to room temperature.</p>
 +
<p>&nbsp;</p>
 +
<p><em>Visual Observations:</em></p>
 +
<p>The orange-colored product was a viscous liquid. A8 was less viscous than A10, A7 and A9.</p>
 +
<p>&nbsp;</p>
 +
<p><em>Analysis:</em></p>
 +
<p>DSC</p>
 +
<p>The product was analyzed by differential scanning calorimetry DSC to identify the glass transition (T<sub>g</sub>) temperature.</p>
 +
<p>The T<sub>g</sub> of A8 is -44.8 &deg;C.&nbsp;</p>
 +
<html>
 +
<img width="750px" heigh="517px" src="https://static.igem.org/mediawiki/2015/e/e2/TU_Darmstadt_Chemie_DSC-Plot_A8.jpg" alt="DSC-Plot A8">
 +
<html/>
 +
<p>Figure 7:DSC- Plot of A8. The T<sub>g</sub> of A8 is -44.8 &deg;C.</p>
 +
<p>&nbsp;</p>
 +
<p>&nbsp;</p>
 +
<h3>A9</h3>
 +
<p><em>Date: </em>16/07/15 &ndash; 17/07/15</p>
 +
<p><em>Lab members: </em>FR, AW</p>
 +
<p>&nbsp;</p>
 +
<p><em>Preparation process:</em></p>
 +
<p>A 20 mL snap-cap vial was loaded with 1.5400 g (3.850 mmol, 0.95 eq.) PEG-400, 0.0205&nbsp;g (0.135&nbsp;mmol, 0.033 eq.) xylitol, 0.5257 g (4.041&nbsp;mmol, 1 eq.) itaconic acid and capped with a pierced aluminium foil. The mixture was heated up to 145 &deg;C with an oil bath on air. No vacuum was applied and the mixture was stirred on air at 145 &deg;C for 21 h. The brown-colored viscous liquid was cooled down to room temperature.</p>
 +
<p>&nbsp;</p>
 +
<p><em>Visual Observations:</em></p>
 +
<p>The brown-colored product was a viscous liquid. A9 was more viscous than A7, A10 and A8.</p>
 +
<p>&nbsp;</p>
 +
<p><em>Analysis:</em></p>
 +
<p>DSC</p>
 +
<p>The product was analyzed by differential scanning calorimetry DSC to identify the glass transition (T<sub>g</sub>) temperature.</p>
 +
<p>The T<sub>g</sub> of A9 is -44.4 &deg;C.</p>
 +
<html>
 +
<img width="750px" heigh="517px" src="https://static.igem.org/mediawiki/2015/9/9d/TU_Darmstadt_Chemie_DSC-Plot_A9.jpg" alt="DSC-Plot A9">
 +
<html/>
 +
<p>Figure 8:DSC- Plot of A9. The T<sub>g</sub> of A9 is -44.4 &deg;C.</p>

Revision as of 19:27, 16 September 2015

Synthesis of prepolymers and characterization

 

Thermal polyesterification of itaconic acid (IA), polyethylene glycol 400

 

Polymers were prepared in dependence on the experimental procedures of Barrett et al.[1]

The procedure requires exact masses. Therefore an analytical balance (4 decimal places) was used and if not otherwise stated PEG as well as itaconic acid were pre-dried before use on a high vacuum line (< 10-3 mbar) overnight.

To avoid contamination with oxygen during the reaction and to remove produced water, common Schlenk technique was applied. As inert gas argon was used.

 

 

A1

Date: 02/06/15 – 03/06/15

Lab members: AW, SZ

 

Preparation process:

A 50 mL Schlenk flask was loaded with 1.213 g (3.033 mmol, 1 eq.) PEG-400 and 0.395 g (3.032 mmol, 1 eq.) itaconic acid and flushed with argon. Within 20 minutes the mixture was heated up to 100 °C with an oil bath and stirred under argon atmosphere. As a colorless melt had formed the vacuum was applied (3·10-2 mbar) and the mixture was stirred at 100 °C for 17 h. The slightly yellow viscous liquid was cooled down to room temperature. 

For a picture of A1 see appendix.

 

Analysis:

No further analyses were performed.

 

 

A2

Date: 09/06/15 – 10/06/15

Lab members: FR, SJ

 

Preparation process:

A 25 mL Schlenk tube was loaded with 2.169 g (5.422 mmol, 1 eq.) PEG-400, 0.705 g (5.420 mmol, 1 eq.) itaconic acid and capped with a septum. Within an hour the mixture was heated up to 145 °C with an oil bath and stirred under argon atmosphere. As a colorless melt had formed the vacuum was applied (< 10-3 mbar) and the mixture was stirred at 145 °C for 24 h. The slightly yellow viscous liquid was cooled down to room temperature.

For a picture of A2 see appendix.

 

Visual Observations:

During the reaction itaconic acid recrystallised on the flask surface which wasn’t dipped into the oil bath. Therefore the ratio between itaconic acid and PEG-400 has changed.

 

Analysis:

The product was analyzed by differential scanning calorimetry DSC to identify the glass transition (Tg) temperature.

The Tg of A2 is -4.7 °C.

DSC-Plot A2

Figure 1: DSC- Plot of A2. The Tg of A2 is -4.7 °C

 

 

A3

Date: 11/06/15 – 12/06/15

Lab members: FR, SJ, AW, SZ

 

Preparation process:

A 10 mL Schlenk tube was loaded with 2.675 g (6.688 mmol, 1 eq.) PEG-400, 0.869 g (6.679 mmol, 1 eq.) itaconic acid and capped with a septum. The mixture was heated up to 145 °C with an oil bath on air. No vacuum was applied and the mixture was stirred on air at 145 °C for 24 h. The orange-colored viscous liquid was cooled down to room temperature.

 

Visual Observations:

The orange-colored product was more viscous than A1 and A2. For a picture of A3 see appendix.

 

Analysis:

DSC

The product was analyzed by differential scanning calorimetry DSC to identify the glass transition (Tg) temperature.

The Tg of A3 is -45.8 °C.

DSC-Plot A3

Figure 2: DSC- Plot of A3. The Tg of A3 is -45.8 °C

 

1H-NMR

The product was analyzed by 1H-NMR to ensure that double bonds are still intact in the product.

Figure 3 shows the spectrum with an enlargement of the olefin region.

NMR A3

Figure 3: 1H-NMR (300 MHz) of A3 in CDCl3

 

Solubility Tests

Solvent

Solubility of Product A3

H2O

good

THF

very good

CHCl3

very good

EtOH

very good

MeOH

good

The solubility of product A3 increases with hydrophobicity of the solvent. But it is still good soluble in water and methanol. This indicates that alkene cross linking during the synthesis not occurred. And the polymer is linear shaped.

 

 

A4

Date: 11/06/15 – 12/06/15

Lab members: FR, SJ, AW, SZ

 

Preparation process:

A 20 mL snap-cap vial was loaded with 1.912 g (4.779 mmol, 1 eq.) PEG-400, 0.622 g (4.781 mmol, 1 eq.) itaconic acid and capped with a septum. The snap-cap vial was flushed with argon for 5 minutes and heated up to 145 °C with an oil bath. The snap-cap vial was almost complete dipped into the oil bath to avoid crystallization on the cold glass surface. The formed colorless melt was then stirred under slight vacuum for 24 h. Afterwards the orange-colored viscous liquid was cooled down to room temperature.

 

Visual Observations:

The orange-colored product was more viscous than A1 and A2. Viscosity and colour were comparable with A3. For a picture of A4 see appendix.

 

Analysis:

DSC

The product was analyzed by differential scanning calorimetry DSC to identify the glass transition (Tg) temperature.

The Tg of A3 is -49.1 °C.

DSC-Plot A4

Figure 4: DSC- Plot of A4. The Tg of A4 is -49.1 °C

 

1H-NMR

The product was analyzed by 1H-NMR to ensure that double bonds are still intact in the product.

Figure 5 shows the spectrum with an enlargement of the olefin region.

NMR A4

Figure 5: 1H-NMR (300 MHz) of A4 in CDCl3.

 

 

A10

Date: 16/07/15 – 17/07/15

Lab members: FR, AW

 

Preparation process:

A 20 mL snap-cap vial was loaded with 2.2750g (5.688 mmol, 1 eq.) PEG-400, 0.7388 g (5.679 mmol, 1 eq.) itaconic acid and capped with a pierced aluminium foil. The mixture was heated up to 145 °C with an oil bath on air. No vacuum was applied and the mixture was stirred on air at 145 °C for 21 h. The brown-colored viscous liquid was cooled down to room temperature.

 

Visual Observations:

The brown-colored product was more viscous than A8 but less viscous than A7 and A9.

 

Analysis:

DSC

The product was analyzed by differential scanning calorimetry DSC to identify the glass transition (Tg) temperature.

The Tg of A10 is -46.9 °C.

DSC-Plot A10

Figure 6:DSC- Plot of A10. The Tg of A10 is -46.9 °C.

 

 

 

Thermal polyesterification of itaconic acid (IA), polyethylene glycol 400 (PEG-400) and xylitol

 

Polymers were prepared in dependence on the experimental procedures of Barrett et al.[1]

The procedure requires exact masses. Therefore an analytical balance (4 decimal places) was used and if not otherwise stated PEG as well as itaconic acid and xylitol were pre-dried before use on a high vacuum line (< 10-3 mbar) overnight.

 

 

A5

Date: 30/06/15 – 01/07/15

Lab members: FR, SJ, AW, SZ

 

Preparation process:

A 20 mL snap-cap vial was loaded with 0.997 g (2.491 mmol, 0.43 eq.) PEG-400, 0.3833 g (2.519 mmol, 0.44 eq.) xylitol, 0.7503 g (5.767 mmol, 1 eq.) itaconic acid and capped with a pierced aluminium foil. The mixture was heated up to 145 °C with an oil bath on air. No vacuum was applied and the mixture was stirred on air at 145 °C for 17.5 h. The orange-colored gel was cooled down to room temperature.

 

Visual Observations:

The orange-colored product was a ductile gel. For a picture of A5 see appendix.

 

Analysis:

Solubility Tests

Solvent

Solubility of Product A5

H2O

no

THF

no

Aceton

no

EtOH

no

MeOH

no

The gel wasn’t soluble in any solvent. Even by applying ultrasound no dissolving occurred. This is probably due to high cross linking with xylitol.

 

 

A6

Date: 30/06/15 – 01/07/15

Lab members: FR, SJ, AW, SZ

 

Preparation process:

A 20 mL snap-cap vial was loaded with 1.2775 g (3.194 mmol, 0.58 eq.) PEG-400, 0.2038 g (1.339 mmol, 0.25 eq.) xylitol, 0.7099 g (5.457 mmol, 1 eq.) itaconic acid and capped with a pierced aluminium foil. The mixture was heated up to 145 °C with an oil bath on air. No vacuum was applied and the mixture was stirred on air at 145 °C for 17.5 h. The orange-colored viscous liquid was cooled down to room temperature.

 

Visual Observations:

The orange-colored product was a ductile gel. For a picture of A6 see appendix.

 

Analysis:

Solubility Tests

Solvent

Solubility of Product A6

H2O

no

THF

no

Aceton

no

EtOH

no

MeOH

no

The gel wasn’t soluble in any solvent. Even by applying ultrasound no dissolving occurred. This is probably due to high cross linking with xylitol.

 

 

A8 

Date: 16/07/15 – 17/07/15

Lab members: FR, AW

 

Preparation process:

A 20 mL snap-cap vial was loaded with 3.4567 g (8.642 mmol, 0.90 eq.) PEG-400, 0.0973 g (0.640 mmol, 0.067 eq.) xylitol, 1.2492 g (9.602 mmol, 1 eq.) itaconic acid and capped with a pierced aluminium foil. The mixture was heated up to 145 °C with an oil bath on air. No vacuum was applied and the mixture was stirred on air at 145 °C for 21 h. The orange-colored viscous liquid was cooled down to room temperature.

 

Visual Observations:

The orange-colored product was a viscous liquid. A8 was less viscous than A10, A7 and A9.

 

Analysis:

DSC

The product was analyzed by differential scanning calorimetry DSC to identify the glass transition (Tg) temperature.

The Tg of A8 is -44.8 °C. 

DSC-Plot A8

Figure 7:DSC- Plot of A8. The Tg of A8 is -44.8 °C.

 

 

A9

Date: 16/07/15 – 17/07/15

Lab members: FR, AW

 

Preparation process:

A 20 mL snap-cap vial was loaded with 1.5400 g (3.850 mmol, 0.95 eq.) PEG-400, 0.0205 g (0.135 mmol, 0.033 eq.) xylitol, 0.5257 g (4.041 mmol, 1 eq.) itaconic acid and capped with a pierced aluminium foil. The mixture was heated up to 145 °C with an oil bath on air. No vacuum was applied and the mixture was stirred on air at 145 °C for 21 h. The brown-colored viscous liquid was cooled down to room temperature.

 

Visual Observations:

The brown-colored product was a viscous liquid. A9 was more viscous than A7, A10 and A8.

 

Analysis:

DSC

The product was analyzed by differential scanning calorimetry DSC to identify the glass transition (Tg) temperature.

The Tg of A9 is -44.4 °C.

DSC-Plot A9

Figure 8:DSC- Plot of A9. The Tg of A9 is -44.4 °C.