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Polymers of N-Vinylpyrrolidone: Synthesis, Characterization and Uses

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Polymers of N-Vinylpyrrolidone: Synthesis, Characterization and Uses Polymer Journal, Vol. 17, No. I, pp 143-152 (1985) Polymers of N-Vinylpyrrolidone: Synthesis, Characterization and Uses F. HAAF, A. SANNER, and F. STRAUB Kunststojjfaboratorium, BASF Aktiengesellschaft D-6700 Ludwigshafen, West-Germany (Received August 20, 1984) ABSTRACT: Polyvinylpyrrolidone (PVP) having molecular weights (Mwl from 2500 to about I million is mainly obtained by radical polymerization in solution. The higher molecular weight type products are polymerized in aqueous solution mostly using hydrogen peroxide as initiator. The polymers thus obtained have hydroxyl and carbonyl end groups. More stable end groups can be obtained by polymerization in solvents, which may act as chain transfer agents and which produce low molecular weight type products. Copolymers especially with monomers such as vinyl acetate and with various acrylic compounds may also be produced by solution polymerization. Popcorn polymerization leads to insoluble PVP. Thereby VP is polymerized without initiator in the presence of small amounts of bifunctional monomers. The polymeric flakes thus formed are highly cross­ linked, mainly due to entanglements. The molecular weight distribution of soluble PVP is broad due to transfer reactions. An unusual property of PVP is its solubility in water as well as in various organic solvents. The glass transition temperature of high molecular weight polymers (Mw= I million) is about l75°C and falls to values under IOOoC with decreasing molecular weight Mw= 2500). PVP forms complexes with various compounds, especially with H-donors such as phenols and carboxylic acids. The complex formed with cross-linked PVP and polyphenols is used commercially for the clarification of beverages. Another commercial use is the complexation of iodine with linear PVP, which leads to effective disinfectants of very low toxicity. Further important applications of PVP in the pharmaceutical field are their use as binding or film forming agents for tablets, and as solubilizing agents for injections. The swelling ability of cross-linked PVP in water is used in disintegrating agents for tablets. In the cosmetic field VP polymers are used as film formers for hair dressing products. Examples of technical applications are adhesives, textile auxiliaries and dispersing agents. KEY WORDS Poly-N-vinylpyrrolidone I Polymerization I Copolymers I Cross-linked Polymers I Properties I Applications I Polyvinylpyrrolidone, also called Povidone or pecially in the pharmaceutical, cosmetic and food briefly PVP, is one of the numerous products 1•2 of industry as well as for numerous technical appli­ the acetylene chemistry founded by Reppe. By cations. In these various fields PVP has rather reaction of acetylene with formaldehyde, 1,4-butine different functions. Because there are considerable diol is obtained which is hydrogenated to butane differences in the requirements, which polymers diol. After oxidative cyclization to butyrolactone have to meet for these diverse applications, three and its reaction with ammonia, pyrrolidone is types of PVP are offered, namely homopolymers of formed by the removal of water. Finally the vinyl different molecular weights, copolymers and cross­ group is introduced to form N-vinylpyrrolidone-2 linked PVP. (1-(2-oxo-pyrrolidinyl)-ethylene). The course of these reactions is shown in Figure I. POLYMERIZATION OF The polymerization of vinylpyrrolidone produces VINYLPYRROLIDONE the polymeric material (Figure 2). In the course of their 40-year history, vinylpyr­ Vinylpyrrolidone can be polymerized either m rolidone polymers have been extensively used, es- bulk, in solution or in suspension. 143 F. HAAF, A. SANNER and F. STRAUB O=CH2 + HC=:CH + CH2 =0 Table I. K-Value and molecular weights of PVP polymerized in solution HO-CH2 -C=:C-CH20H fill K-Value Mw M. dlg- 1 HO-CH2 -CH2 -CH2 -CH2 0H 12 0.05 2,500' 1,300 17 0.09 10,000• 2,500b 25 0.16 25,ooo· 6,000b Oo 30 0.22 40,ooo· lO,OOOb 0 90 1.6 1.1 Milion• 150,000' I+NH3 .-H20 • Light scattering. b Vapor pressure osmometry. Oo ' Gel permeation chromatography. N H cases an aldehyde functional group is found as the second end group. This can be explained by the fact Oo that the second hydroxyl end group, which is form­ N ed during chain termination, continues to react by I CH=CH2 splitting off pyrrolidone. Consequently polyvinyl­ Figure 1. Synthesis of N-vinylpyrrolidone from acet­ pyrrolidone produced in aqueous solution contains ylene and formaldehyde. small amounts of pyrrolidone. No evidence can be found for other chain termination reactions such as CH2-CH2 disproportionation. I \ I \ The polymerization of vinylpyrrolidone in or­ CH2 c=o CH2 c=o ganic solvents such as alcohols, toluene, etc. pro­ 'N/ 'N/ ceeds in a more complicated way (Figure 4). I I Using organic peroxides such as di-tertiary-butyl­ CH-CH2 CH-CH2 n peroxide or dicumyl peroxide, alkoxy radicals are formed, which produce solvent radicals by H abs­ Figure 2. Polymerization of vinylpyrrolidone. traction. In this case it is this solvent radical, not the alkoxy radical of the initiator, which initiates the The cationic polymerization with BF3 only leads polymerization. While the chain propagation pro­ to oligomers3.4 and has no technical importance. ceeds as expected, it was proved that the chain Polymers with degrees of polymerization of I 0- termination takes place by H abstraction from the 100,000 are obtained by radical polymerization. solvent-and hardly by recombination or dispropor­ This corresponds to molecular weights of 1,000-10 tionation. An alkyl end group and a solvent million. In industry polymers having molcular radical are formed; the solvent radical again in­ weights of 2,500-1 million are mainly produced itiates polymerization. The proof for this polymeri­ (Table 1). zation mechanism is obtained by H NMR spectros­ Vinylpyrrolidone is generally polymerized in copy (Figure 5). aqueous solution using hydrogen peroxide as ini­ In the case of carefully purified polymers pro­ tiator. 5 Figure 3 shows a simplified scheme. duced in toluene using di-tertiary-butyl peroxide, Thereby the molecular weight is regulated by the the presence of aromatic groups of the toluene can concentration of hydrogen peroxide, i.e., the higher clearly be seen in the NMR-spectrum, though the the amount of hydrogen peroxide the lower the polymer product no longer contained any residual molecular weight of the polyvinylpyrrolidone pro­ solvent (gas chromatographic measurements). duced. In aqueous solution hydroxy radicals are Similarly the H NMR spectrum as well as the 13C generated from hydrogen peroxide, thus forming NMR spectrum of polymers, which are produced in the end groups of the polymer. However, in most isopropanol solution with dicumyl peroxide as 144 Polymer J., Vol. 17, No. 1, 1985 Polymers of N-Vinylpyrrolidone: Synthesis, Characterization, and Uses lnitiatJon: Heat HO• + •OH H UoN H UoN I I I I HO• + c-c HO -C-C• I I I I H H H H Propagation : H OoN I I I I HO- C- C • + HO c- c c - c • I I I I H H H H H H n Termination HI I HI I H CJ=o I I I I HO { c - c c - c • + •OH ----.. HO { C - c C - C - OH I I I I I I I I H H H H H H H H n n H N H I I I Ho c-c c-c =O + Oo I I I I N H oiH H H I t H n Figure 3. Polymerization mechanism of VP in aqueous solution. Initiation: Heat ROOR - RO· + ·OR RO· + SH ROH + S· Solvent - Uo Oo H N H N I I I I S• + c=c S -C-C• I I - I I H H H H Propagation : Oo HCNJ=o HCNJ=o N ' s- c- c. + n C=C s c- c c -C• ' . ' H H H H - H H H n Termination by Chain Transfer: H N H N I I I CJ=oI {HV1HCJ=oI I I I s c - c c -c. + s H '----+ s c - c c - c - H + S· 1 011 1 1 I I I I tHH HH HH HH n n Figure 4. Polymerization mechanism of VP in organic solution. Polymer J., Vol. 17, No. I, 1985 145 F. HAAF, A. SANNER and F. STRAUB in Toluene HQ- t H-NMR-S•gnals __} of PVP ______ __ 0 ppm 10 000 35 000 - Molweight [Dalton] in Isopropanol Figure 6. Gel permeation chromatography of PVP. Conditions: aqueous solution with 0.08 m. Tri(hy­ droxymethyl)aminomethan/HCl, pH 4.65. Flow rate 1 mljmin, 2J'C. 100 'E Figure 5. NMR-spectra of PVP polymerized in or­ E. Q) ganic solvents. 0 c: 1ii"' 10 iS 7 Permeability Limit 5 Through the "0c: initiator, show the fragments of isopropanol. w Kidney Capillaries Polyvinylpyrrolidone produced in organic solution .9 2 "0c: 90 K-Value in the presence of peroxides contains an end group w 17 25 30 of the solvent radical and a hydrogen atom from 1 000 10 000 100 000 1 000 000 termination due to chain transfer. Since there is no Molecular Weight Mw splitting off of any pyrrolidone at the polymer end, Figure 7. End to end distance of the coiled chains vs. these polymer products are purer and--due to the K-value and molecular weight. Solvent: 0.9% NaCI in lack of aldehyde end groups-more stable towards water. oxidizing agents than those products, which are polymerized in water with hydrogen peroxide as the formation of the high molecular weight products initiator. due to grafting of the polymer chain. In the case of the polymerization in organic Polyvinylpyrrolidone in solution probably exists solution, low molecular weights are obtained due to as a random coil; suggestions in the literature6 the transfer reactions of the solvent.
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