V-Vinyl-2-pyrrolidinone

TABLE 1, PROPERTIES OF V-VINYL-2-PYRROLIDINONE (COMMERCIAL PRODUCTION)... 

Dole [67, 68] observed that small molecules associate firmly with functional sites in polymeric materials. He studied sorption of water and organic vapors by synthetic high molecular weight polymers. He noted that the ratio (a/N) of sorbed molecules (a) to available adsorption sites (N, i.e. the total number of functional groups in the polymer) increases with the partial pressure of the vapor being sorbed. In the case of water sorption at 100% RH by poly(/V-vinyl 2-pyrrolidinone) a/N was almost one, and in the case of water sorption by poly(vinyl methoxyacetal) [68] it was even greater than one. 

Pieracci, J., Crivello, J.V. and Belfort, G. 2002. UV-assisted graft polymerization of V-vinyl-2-pyrrolidinone onto polyfether sulfone) ultrafiltration membranes using selective UV wavelengths. 14 256-265. 

In most publications, particularly in commercial data sheets, the term V-vinyl-pyrrolidone with the abbreviation NVP is used for the monomer and PVP is used for the corresponding polymer therefore, these abbreviations are used here. However, frequently other names are used, such as iV-vinyl-2-pyrrolidone V-vinyl-2-pyrrolidinone l-vinyl-2-pyrrolidinone l-vinyl-2-pyrrohdone l-vinylpyrrolidin-2-on l-ethenyl-2-pyrrolidinone and 2-pyrrohdinone-l-ethenyl. 

N-Vinyl-2-Pyrrolidinone. Commonly called vinylpyrrolidinonc or VP, Af-vinyl-2-pyrrolidinone is a clear, colorless liquid that is miscible in all proportions with water and most organic solvents. IL can polymerize slowly by itself but can be easily inhibited by small amounts of ammonia, sodium hydroxide (caustic pellets), or antioxidants such as N, V -di-xeobutyl-p-phcnylcncdiaminc. It is stable in neutral or basic aqueous solution but readily hydrolyzed in the presence of acid to form 2-pyrrolidinonc and acetaldehyde. Properties are given in Table 1. 

Beilstein Handbook Reference) BRN 0110513 EINECS 201-800-4 NSC 10222 V-Pyrol Vinyl-2-pyrrolidone Vinylbutyrolactam Vinylpyrrolidin-one N-Vinyl-2-pyrrolidinone Vinylpyrrolidone N-Vinyl-2-pyrfolidone N-Vinyl pynolidone N-Vinylpyrrolidin-one. Liquid mp = 13.5 bp400 = 193 , bpii = 93 d = 1.04. 

White, T.J., Liechty, W.B., Natarajan, L.V., Tondiglia, V.P., Bunning, T.J., Guymon, C.A. The influence of N-vinyl-2-pyrrolidinone in polymerization of holographic polymer dispersed liquid crystals (HPDLCs). Polymer 47, 2289-2298 (2006)... 

J. Pieracci, D.W. Wood, J.V. CriveUo, G. Belfort, UV-assisted graft polymerization of N-vinyl-2-pyrrolidinone onto poly (ether sulfone) ultrafiltration membranes Comparison of dip versus immersion modification techniques, Chem Mater, 12 (2000) 2123-2133. 

Dispersancy Solution copolymers are comparatively easy to produce in dispersant form as copolymerization with an appropriate polar monomer is relatively straightforward. If the polar monomer is also a methacrylate, reactivity ratios are essentially the same and no special procedures are required to produce random copolymers. Commercial examples have included dimethyl (or diethyl)aminoethyl methacrylate [11], hydroxyethyl methacrylate [12] and dimethylamino-ethyl methacrylamide [13]. 2-Methyl-5-vinyl pyridine [14] has also been used commercially, reactivity ratios are such that it copolymerizes slightly faster than alkyl methacrylates. Although composition drift is not severe, it should be added in a programmed fashion if a uniform distribution is desired. V-vinyl pyrrolidinone, in contrast, copolymerizes very sluggishly with methacrylates and is best incorporated via a graft reaction [15], sometimes also grafted in combination with V-vinyl imidazole [16]. Since solution chemistry is used to produce dispersant polymethacrylates, like preparation of the base polymer, only relatively simple process modifications are necessary to produce dispersants commercially. 

Addition of 5-substituted 2-pyrrolidinones to methyl glyoxylate produces useful precursors (190) to exocyclic /V-acyliminium ions (equations 132).156 The preferred iminium ion geometry is most probably ( ) as depicted in (191) for steric reasons. This geometry explains the stereochemical relationship between the ring junction hydrogen atom and the ester function in the products (192) and (193). Best yields are achieved by using the thermal cyclization of intermediate mesylates, and the major products have the ester and vinyl function trans.156... 

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