Polyvinylamine

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Structural formula
Structural formula polyvinylamine
General
Surname Polyvinylamine
other names
  • Polyaminoethylene
  • Poly (1-aminoethylene)
CAS number 26336-38-9
Monomer Vinylamine
Molecular formula of the repeating unit C 2 H 5 N
Molar mass of the repeating unit 43.07 g mol −1
Type of polymer

Thermoplastic

Brief description

colorless, water-soluble plastic

properties
Physical state

firmly

safety instructions
GHS labeling of hazardous substances
no classification available
H and P phrases H: see above
P: see above
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Polyvinylamine , also known as polyaminoethylene , ( abbreviation PVAm ) is a thermoplastic polymer . Since PVAm cannot be produced by direct polymerisation of the base monomer vinylamine , it can only be obtained by a polymer-analogous reaction . It was not available in large-scale quantities until the beginning of the 21st century.

history

In 1944, polyvinylamine was first produced as a by-product from ethanolamine , phthalic anhydride and acetic anhydride in several stages.

In the early 1980s, PVAm became more accessible through the polymerization of N-vinylformamide .

Manufacturing

Imine-enamine tautomerism of vinylamine

The base monomer vinylamine cannot be isolated as such. In vinylamine there is an imine-enamine tautomerism and the equilibrium is almost completely on the side of the imine, which cannot be polymerized to polyvinylamine. The synthesis of PVAm is therefore only possible indirectly via a polymer-analogous reaction .

For example, polyvinylamine can be produced by hydrolysis of poly-N-vinylamides, such as poly-N-vinyl acetamide or poly-N-vinylimides, such as poly-N-vinyl succinimide, since the base monomers are easily accessible here. Polyvinylamine can also be produced from polyacrylamide by Hofmann degradation .

The large-scale synthesis of polyvinylamine

On an industrial scale, polyvinylamine has only been produced since 2002 by polymerizing N-vinylformamide to polyvinylformamide and subsequent alkaline hydrolysis . Products with different degrees of hydrolysis can be produced. The world's largest manufacturer of PVAm is BASF in Ludwigshafen am Rhein . The company sells PVAm under the brand name Luredur .

properties

Polyvinylamine is strongly basic and very easily soluble in water. Depending on the pH, it reacts as a cationic polyelectrolyte . Together with polyethyleneimine , it currently has the highest charge density of all technical polymers (23 milliequivalents per gram). As a polychelatogen , PVAm is able to coordinate a number of heavy metal ions via the amino groups.

The primary amino groups of PVAm can be reacted with other chemicals in a variety of ways.

use

PVAm is mainly used in the paper industry as a wet strength agent. But it is also used there for fixation and dry consolidation.

Further fields of application are: flocculants (for example in sewage technology), personal care products, superabsorbents , dispersants , corrosion protection and surface modification.

PVAm can be used as a non-viral gene transfer system to introduce DNA into animal cells ( transfection ).

By polymerization of N-vinylformamide with olefins or acrylic derivatives , a plurality unterschiedlichster can co-polymers produced.

literature

Individual evidence

  1. ↑ Uta Bilow: Tailor-made suit for prostheses. In: deutschlandfunk.de. August 26, 2002, accessed May 10, 2019 .
  2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  3. ↑ a b Entry on vinylamine polymers. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.
  4. ↑ J. Zomlefer et al. a .: Attempted Preparation of Polyvinylamine. In: Journal of Organic Chemistry 1944, p. 500, doi: 10.1021 / jo01188a003 .
  5. ↑ a b c d e f R. H. Wittke: Representation and investigation of functionalized polymer surfaces. (PDF) Dissertation, University of Duisburg-Essen, 2005, urn : nbn: de: hbz: 464-duett-09092005-1710211 .
  6. ^ GV Seguel u. a .: Structure and properties of poly (vinylamine) -metal complexes. In: Angewandte Makromolekulare Chemie 251/1997, pp. 97-106, doi: 10.1002 / apmc.1997.052510109 .
  7. ↑ Polyvinylformamide and polyvinylamine ( Memento from June 28, 2007 in the Internet Archive ). In: News from Chemistry 49/2001 (PDF; 179 kB.)
  8. ↑ S. Gersting: Influence of extracellular factors on structure and function not gene vectors. Dissertation, LMU Munich, 2003, DNB 967283493 .
  9. ^ A. Madl, S. Spange: Synthesis and application of oligo (vinylamine). In: Macromol. Symp. 161/2000, pp. 149-157, doi : 10.1002 / 1521-3900 (200010) 161: 1 <149 :: AID-MASY149> 3.0.CO; 2-P .