Synthesis and Secondary-Ion Mass Spectrometry of Linear Single Oligomers of Nylon-6

Macromolecules

Volumn 32, Issue 5, 1999, Pages 1367-1374

  Reddy, Srinivasa S ^a   Dong, Xia ^a   Murgasova, Renata ^a   Gusev, Arkady I ^a   Hercules, David M ^a  

^a VANDERBILT UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; DIMERS; HYDROGEN; MOLECULAR STRUCTURE; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLIGOMERS; SECONDARY ION MASS SPECTROMETRY; SILVER; SODIUM; SYNTHESIS (CHEMICAL);

AMINOHEXANOIC ACID;

NYLON POLYMERS;

EID: 0033537560     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma9807670     Document Type: Article

References (25)

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16. This salt is sticky in nature; after repeated washings with an excess of ether a free-flowing solid can be obtained. This solid is dried overnight in vacuo to remove the traces of volatile trifluoroacetic acid impurities.
17. The salt of the dimer is less sticky than the salt of the monomer. The treatment for compound 4 was employed to remove the trace impurities of volatile trifluoroacetic acid and to obtain a free-flowing solid. In the preparation of higher oligomers, salts of the tetramer and octamer were more free flowing than the dimer salt.
18. The yields for each coupling step: dimer, 40 mol %; tetramer, 53 mol %; hexamer, 80 mol %; octamer, 75 mol %, 77 mol. The higher oligomer yields were increased by heating the reaction mixture at 50-60°C for about 48 h. Dimer and tetramer yields also can be increased by employing the same process. Small-scale reactions produced higher yields than large-scale reactions.
19. 1H NMR were recorded in DMSO-D6 using a Bruker 300 MHz instrument. The octamer and dodecamer were made soluble by heating the solution, whereas the dimer, tetramer, and hexamer were soluble at room temperature.
20. The peak ratio of 7.75 ppm to 6.75 ppm peaks for dimer is 15%, tetramer 18%, hexamer 25%, octamer 31%, and for dodecamer 40% higher than the expected value. The increase in the error for these oligomers as the number of repeating units increased may be due to the fact that the peak at 6.75 ppm, which corresponds to the end group BOC-NH proton (which is just one proton), is difficult to see in the larger oligomer chain.
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