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Polyvinylpolypyrrolidone
Polyvinylpolypyrrolidone
Polyvinylpolypyrrolidone
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Polyvinylpolypyrrolidone
Names
IUPAC name
1-ethenylpyrrolidin-2-one
Other names
  • Polyvinyl polypyrrolidone
  • crospovidone
  • crospolividone
  • E1202
  • Kollidon CL
Identifiers
Abbreviations PVPP
ChemSpider
  • none
ECHA InfoCard 100.110.608 Edit this at Wikidata
E number E1202 (additional chemicals)
Pharmacology
A07BC03 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Polyvinylpolypyrrolidone (polyvinyl polypyrrolidone, PVPP, crospovidone, crospolividone, or E1202) is a highly cross-linked modification of polyvinylpyrrolidone (PVP).

This cross-linked form of PVP is used as a disintegrant (see also excipients) in pharmaceutical tablets.[1]

PVPP is insoluble in water, though it still absorbs water and swells very rapidly generating a swelling force. This property makes it useful as a disintegrant in tablets.[citation needed]

PVPP can be used as a drug, taken as a tablet or suspension to absorb compounds (so-called endotoxins) that cause diarrhea. (Cf. bone char, charcoal.)[citation needed]

It is also used as a fining to extract impurities (via agglomeration followed by filtration). It is used in winemaking. Using the same principle it is used to remove polyphenols in beer production and thus clear beers with stable foam are produced.[2] One such commercial product is called Polyclar. PVPP forms bonds similar to peptidic bonds in protein (especially, like proline residues) and that is why it can precipitate tannins the same way as proteins do.[3]

PVPP is used as a stabiliser.[citation needed]


Safety

[edit]

Autopsies have found that crospovidone/PVPP contributes to pulmonary vascular injury in substance abusers who have injected pharmaceutical tablets intended for oral consumption.[4]


See also

[edit]

References

[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

Polyvinylpolypyrrolidone

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from Grokipedia
Polyvinylpolypyrrolidone (PVPP), also known as crospovidone or insoluble , is a synthetic, cross-linked homopolymer derived from the of N-vinyl-2-pyrrolidone, with the repeating unit formula (C₆H₉NO)ₙ. It is produced using a caustic catalyst or cross-linking agents like N,N'-divinylimidazolidone, resulting in a white, hygroscopic powder that is insoluble in , , , and most organic solvents. This insolubility, combined with its high surface area and ability to swell upon absorption, makes PVPP an effective adsorbent for polyphenols, , proteins, and toxins via hydrogen bonding and complex formation. PVPP exhibits notable physical and chemical properties that distinguish it from its soluble counterpart, linear (PVP). As a non-ionic with a content of 11–12.8% and a range of 5.0–8.0 in 1% aqueous suspension, it demonstrates excellent swelling capacity—expanding up to approximately 100 times its original volume upon water absorption—without dissolving, which enables rapid disintegration in moist environments. Its , physiological inertness, and low toxicity have led to approvals as a (E 1202 in the EU) and pharmaceutical by regulatory bodies like the FDA. However, PVPP can form peroxides upon prolonged exposure to heat, oxygen, and light, necessitating proper storage conditions. In applications, PVPP serves primarily as a fining and stabilizing agent in the beverage industry, where it removes haze-forming polyphenols and anthocyanins from wine, , and fruit juices at dosages of 15–80 g/hL, improving clarity and without significantly altering aroma or flavor profiles. In pharmaceuticals, it functions as a superdisintegrant in tablets and capsules, enhancing dissolution rates for poorly soluble actives by wicking and swelling mechanisms, and is also used in controlled-release formulations and as a binder in . Additionally, PVPP acts as an adsorbent in to mitigate toxicity, such as aflatoxins, by binding and excreting them, and in settings for purifying extracts by eliminating interfering phenolics. Its versatility extends to food supplements as a stabilizer in tablet forms, underscoring its role in enhancing product stability and efficacy across industries.

Chemical Structure and Properties

Molecular Structure

Polyvinylpolypyrrolidone (PVPP) is a cross-linked homopolymer formed from the N-vinyl-2-pyrrolidone, which has the molecular \ceC6H9NO\ce{C6H9NO} and consists of a five-membered ring (pyrrolidin-2-one) with a (\ce−CH=CH2\ce{-CH=CH2}) attached to the atom at position 1. The IUPAC name for this is 1-ethenylpyrrolidin-2-one. The repeating unit of the is \ce(C6H9NO)n\ce{(C6H9NO)_n}, where nn represents a high , but PVPP lacks a specific molecular or weight due to its variable cross-linking density. The base is designated as poly(1-ethenylpyrrolidin-2-one), with cross-links integrated into the structure to form an insoluble network. Cross-linking in PVPP occurs through the formation of covalent bonds between chains, creating a three-dimensional matrix that renders the material insoluble. This is primarily achieved via a popcorn polymerization process of N-vinyl-2-pyrrolidone, which induces spontaneous branching and cross-linking without external agents, though additional cross-linking agents such as divinyl glycol, diallyl compounds, or can be employed to form covalent bridges between chains. The degree of cross-linking is typically controlled at 1-10% cross-linker content relative to the , resulting in a gel-like polymeric with branch points that interconnect linear chains. Visually, the molecular of PVPP features a networked arrangement of (PVP) chains—unlike the linear, unbranched chain of non-cross-linked PVP—where cross-links manifest as covalent junctions linking multiple segments into an extended, porous matrix.

Physical Properties

Polyvinylpolypyrrolidone (PVPP), also known as crospovidone, appears as a to off-white, free-flowing powder that is practically odorless. Its true density is approximately 1.22 g/cm³, while the ranges from 0.1 to 0.5 g/cm³ depending on the grade, which influences its handling and flow properties in industrial applications. Commercial grades typically feature particle sizes of 30-100 μm, with finer variants around 20-50 μm and coarser ones up to 140 μm, affecting dissolution rates and in formulations. PVPP is highly hygroscopic, capable of absorbing up to about 30-40% of its weight in at very high relative humidity (e.g., >90% RH) without dissolving, due to its cross-linked that prevents solubilization. It exhibits rapid swelling behavior in , expanding by 95-200% in volume (corresponding to 2-3 times original volume for standard grades, or up to 400-900% for superfine grades) owing to hydrophilic groups along the polymer chains, while remaining insoluble and forming no gel. Thermally, PVPP has a temperature of 160-180°C and decomposes above 200°C without , demonstrating good stability under moderate heating. In terms of , PVPP is insoluble in , alcohols, and most organic solvents, in contrast to the soluble linear (PVP). This insolubility arises from its cross-linked polymeric network, enabling its use in applications requiring structural integrity in aqueous environments.

Chemical Properties

Polyvinylpolypyrrolidone (PVPP) exhibits polarity due to the groups within its pyrrolidone rings, which serve as hydrogen bonding sites for adsorbing polar molecules such as polyphenols. Despite its insolubility, PVPP possesses hydrophilic characteristics that facilitate interactions with aqueous solutions containing . The binding mechanism of PVPP primarily involves hydrogen bonding between the carbonyl oxygen of the pyrrolidone units and the hydroxyl groups of s like and , supplemented by hydrophobic interactions and van der Waals forces. This results in an adsorption capacity of approximately 90 mg of s per gram of PVPP, though capacities can vary based on polyphenol type and concentration. The adsorption process follows a Langmuir isotherm model, where binding sites on PVPP become saturated at high polyphenol concentrations, indicating adsorption without multilayer formation. PVPP demonstrates chemical inertness under neutral conditions ranging from 4 to 8 and remains stable to up to 100°C, with minimal degradation during typical processing. However, it degrades in the presence of strong acids, bases, or oxidants, which can disrupt the cross-linked structure. Performance is -dependent, with optimal binding affinity at pH 3-5, where hydrogen bonding is enhanced, and degradation is negligible over extended periods in beverage matrices. Swelling in aqueous media further aids accessibility to these binding sites.

Synthesis and Production

Polymerization Process

Polyvinylpolypyrrolidone (PVPP) is produced via free radical of N-vinylpyrrolidone (NVP) , forming a highly cross-linked, insoluble network essential for its applications. The process typically employs a popcorn mechanism, a form of proliferous that generates irregular, porous particles without requiring an external cross-linking agent in the primary method. In this approach, NVP is in an aqueous medium using an catalyst, such as (0.3–1.5% by weight relative to NVP), under an inert atmosphere at temperatures ranging from 130–170°C. The reaction proceeds for approximately 3 hours, during which cross-linkers like 1-vinyl-3-ethylidenepyrrolidinone (about 1.5%) or ethylidene-bis-3-(N-vinylpyrrolidinone) (0.1%) form spontaneously, creating physical entanglements and chemical bonds that render the insoluble. An alternative synthesis involves the addition of a bifunctional cross-linking agent, such as N,N'-divinylimidazolidone-2 (0.5–10% by weight, preferably 1–3%), to NVP in (25–100% by weight relative to ). This method uses radical initiators like dibenzoyl (0.005–0.03%) or to initiate the reaction at 30–106°C, often reaching a of around 102°C under . The exhibits an induction period of about 90 minutes followed by rapid completion in 15–20 minutes, yielding a highly cross-linked structure through covalent bonds between polymer chains. Other initiators, such as azoisobutyronitrile (AIBN) or organic peroxides, can be employed in similar radical pathways, sometimes at 50–95°C in organic solvents like 2-propanol, though aqueous conditions are preferred to avoid residual solvents. The simplified radical polymerization reaction can be represented as: \cenCH2=CH−N<−>[−CH2−CH(N<)−]n\ce{n CH2=CH-N< ->[-CH2-CH(N<)-]_n} where N< denotes the pyrrolidone ring, with cross-links denoted by bridges between chains. Following polymerization, the product is isolated by diluting the reaction mixture with to 5–30% solids, filtering or centrifuging to separate the , and washing repeatedly with to remove unreacted NVP (ensuring residual levels below 0.1%). The washed is then dried under vacuum at 50–80°C, often followed by milling or to achieve desired particle sizes without altering the cross-linked network. These steps ensure high purity and control the 's swelling capacity while maintaining its insoluble nature.

Commercial Manufacturing

Commercial production of polyvinylpolypyrrolidone (PVPP) began in the early 1960s, initially developed by General Aniline & Film () for use as a beverage fining agent, with subsequent expansion by companies like to meet growing industrial demands. The industrial process typically involves batch in specialized reactors, where N-vinylpyrrolidone monomer is heated with a strong caustic agent, such as sodium or , under popcorn conditions to form cross-linked, insoluble particles. Following , the reaction mixture is cooled, slurried in water, filtered to separate the , and subjected to with dilute acid like to neutralize residual . The resulting wet cake is then washed extensively and dried using spray or vacuum drying methods to produce a free-flowing powder suitable for commercial distribution. Cross-linking in PVPP is controlled through the degree of cross-linking achieved via formation during or by adding agents like N,N'-divinylimidazolidone in alternative methods, which determines the polymer's swelling behavior and particle morphology. For beverage-grade products like the , higher cross-linker ratios yield coarser particles with lower swelling for efficient , while pharmaceutical grades employ lower ratios to produce finer, more swellable particles optimized for disintegration. Purification steps are critical to remove unreacted and impurities, typically achieved through multiple washes, stripping, or extraction processes, ensuring residual N-vinylpyrrolidone levels remain below 10 ppm as required by pharmacopeial standards like USP/NF for pharmaceutical applications. Commercial yields for PVPP production generally range from 90% to 95%, with the energy-intensive drying stage accounting for 20-30% of overall production costs due to the need for precise control to avoid particle agglomeration. Variations in production cater to specific end-use requirements, with pharmaceutical-grade PVPP (conforming to USP/NF monographs) featuring fine particle sizes achieved via post-drying milling, while food-grade PVPP (designated E1202 in the ) uses for coarser, more robust particles suited to beverage processing. measures, including analysis and residual testing, ensure consistency across grades, with stringent limits on and microbial content for both variants.

Applications

Beverage Fining Agent

Polyvinylpolypyrrolidone (PVPP) serves as a key fining agent in the production of alcoholic beverages, particularly wines and beers, where it targets polyphenols responsible for , oxidation, and instability. In , PVPP selectively adsorbs low molecular weight phenolics such as catechins, anthocyanins, and , preventing protein-polyphenol interactions that lead to haze formation during storage. This adsorption occurs primarily through hydrogen bonding and hydrophobic interactions between the polymer's polar groups and the phenolic hydroxyls. In , PVPP is typically added at dosages of 10-50 g/hL, with contact times ranging from 1 to 24 hours, often during clarification, , or early maturation stages for optimal results. It is introduced as a or , stirred into the must or wine, and then removed via , achieving 95-99% elimination of the agent itself to ensure residue levels below regulatory thresholds. The permits a maximum dosage of 80 g/hL for wine treatment, reflecting its established safety profile in oenological practices. For brewing, PVPP enhances beer clarity and foam stability by removing proanthocyanidins and other haze-active polyphenols, which otherwise contribute to colloidal instability. Typical addition rates are 5-20 g/hL, applied pre-filtration during maturation or conditioning, with short contact times of 5-30 minutes to avoid over-treatment that could affect flavor or . Like in , PVPP is filtered out alongside other aids such as kieselguhr, ensuring high removal efficiency. The use of PVPP offers several benefits, including reduced oxidation risk by lowering reactive levels, improved color stability, and enhanced shelf life without compromising sensory attributes. As a synthetic , it provides a vegan alternative to animal-derived fining agents like , aligning with growing demand for plant- or synthetic-based processing aids in beverage production. For instance, in white wines, PVPP is particularly effective at preventing enzymatic and non-enzymatic by targeting oxidizable phenolics, maintaining fresh appearance and aroma profiles. Effectiveness is quantified through haze potential tests, where PVPP treatments reduce polyphenol content by 50-90%, significantly lowering turbidity and improving long-term stability. In beers, it can remove up to 92% of specific proanthocyanidins like procyanidin B3 at higher doses, correlating with reduced chill haze formation.

Pharmaceutical Disintegrant

Polyvinylpolypyrrolidone, commonly referred to as crospovidone in pharmaceutical contexts, functions as a superdisintegrant in tablet formulations by rapidly swelling upon contact with aqueous fluids. This swelling disrupts the tablet structure through wicking and capillary action, leading to disintegration times often under 30 seconds in optimized formulations. Typical usage levels range from 2% to 5% w/w, providing efficient breakdown without excessive gel formation that could hinder dissolution. Beyond disintegration, crospovidone acts as an intestinal adsorbent, binding bacterial endotoxins and s to alleviate gastrointestinal disturbances, including (ATC code A07BC03). This adsorption mechanism forms a protective mucosal layer, reducing absorption and supporting symptomatic relief in oral preparations. In , particularly , it has been employed as an active agent for such intestinal disorders due to its high affinity for polyphenolic s. Crospovidone offers key formulation advantages, including improved bioavailability for poorly soluble active pharmaceutical ingredients via coevaporation or solid dispersion techniques, where its porous structure enhances drug solubilization and release. It is highly compatible with direct compression processes, improving flowability and compactibility of powder blends for robust tablet production. Available grades, such as BASF's Kollidon CL (coarse particles for standard release), CL-F (fine for faster onset), and CL-SF (superfine for rapid action), allow customization based on particle size distribution—finer grades accelerate swelling for immediate-release applications, while coarser ones suit controlled-release needs. In clinical applications, crospovidone is routinely included in and tablets to ensure quick disintegration and onset of action, as seen in products like Ultra Strength (containing crospovidone for calcium carbonate release) and various acetaminophen formulations. The (USP) monograph mandates high purity standards, including not more than 10 ppm and limits on residual vinylpyrrolidone (≤10 ppm) and peroxides, ensuring suitability for pharmaceutical use.

Other Industrial Uses

In cosmetics, polyvinylpolypyrrolidone (PVPP) serves as a stabilizer in formulations such as hair sprays and lotions, where it binds impurities and maintains stability without dissolving in the product, typically at concentrations of 0.5-2%. Its insolubility allows it to act as a suspending agent for insoluble solids while preventing separation of oil and liquid components. Beyond its primary role in alcoholic beverages, PVPP functions as a in juices by adsorbing polyphenols and haze-forming compounds, enhancing visual clarity without altering flavor profiles. As the E1202, it is approved for use in non-alcoholic drinks, where it stabilizes suspensions and removes to prevent cloudiness. In , PVPP also acts as a stabilizer in gels, improving texture and preventing syneresis through its adsorptive properties. PVPP finds application as an alternative to traditional ion-exchange resins in , where its adsorptive capacity targets organic impurities like iodine or phenolics in purification processes. In , it serves as an adsorbent in columns for separating polyphenols from natural extracts, leveraging hydrogen bonding between its carbonyl groups and phenolic hydroxyls for selective retention. Emerging research explores PVPP's role in as a capping agent for silver nanoparticles, where it stabilizes dispersions and enhances properties by preventing aggregation. However, PVPP is unsuitable for high-heat industrial processes, as it undergoes above 175°C, leading to mass loss and structural breakdown.

Safety and Regulation

Health and Toxicity

Polyvinylpolypyrrolidone (PVPP), also known as crospovidone, demonstrates low acute oral . In rats, the (LD50) exceeds 5 g/kg body weight, indicating minimal risk from ingestion under normal conditions. This low stems from PVPP's high insolubility in water and gastrointestinal fluids, which prevents systemic absorption; the material passes through the digestive tract largely unchanged and is excreted in feces. Consequently, PVPP is permitted by the U.S. as a in , removed by to ensure no significant residues remain, based on its inert nature and lack of . Regarding dermal and exposure, PVPP is non-irritating to the skin and non-sensitizing in standard tests, with no evidence of from direct contact. However, as a fine powder, of PVPP may cause mechanical to the , similar to other inert particulates, though it does not produce chemical or long-term lung damage at typical exposure levels. Occupational exposure limits for PVPP follow general standards for nuisance , with the () () set at 15 mg/m³ for total and 5 mg/m³ for the respirable fraction over an 8-hour time-weighted average. A notable health risk arises from misuse, particularly the intravenous injection of crushed pharmaceutical tablets containing PVPP as a disintegrant. This practice, common among individuals abusing opioids or other drugs, leads to of insoluble PVPP particles in the pulmonary vasculature, triggering granulomatous inflammation, angiothrombosis, and . Case studies from intravenous drug users, including autopsies revealing crospovidone deposits in tissue, have documented severe complications and fatalities, with the issue recognized since the and amid rising tablet abuse. Chronic exposure to PVPP shows no evidence of carcinogenicity; the related (PVP) is classified by the International Agency for Research on Cancer (IARC) as Group 3 (not classifiable as to its carcinogenicity to humans), and PVPP follows suit due to its inert profile. The European Food Safety Authority's 2020 re-evaluation confirmed no genotoxic potential or , with negative results across bacterial mutagenicity, mammalian cell mutation, and aberration assays. Allergenicity is rare, though isolated cases of , including , have been reported in sensitive individuals exposed to PVP-based excipients, potentially extending to PVPP via similar mechanisms. Given its negligible absorption, the EFSA deems no (ADI) necessary for dietary exposure.

Environmental Impact

Polyvinylpolypyrrolidone (PVPP) exhibits poor biodegradability due to its highly cross-linked , which resists microbial degradation. Standard tests, such as the OECD 301 guideline, demonstrate less than 20% degradation after 28 days, with specific measurements showing only 11% under aerobic conditions. This persistence stems from the polymer's insoluble nature and the stability of its pyrrolidone rings and cross-links, limiting enzymatic breakdown in natural environments. In , particularly from beverage production where PVPP is used as a fining agent, the is largely removed through processes, achieving over 99% efficiency in separating the insoluble particles from the liquid phase. The remaining residues typically settle into during , preventing significant release into effluents. This fate minimizes direct aquatic exposure but directs PVPP to solid waste streams for further management. Ecotoxicity assessments indicate low risk to aquatic organisms, with LC50 values exceeding 1000 mg/L for fish (e.g., juvenile , 96-hour exposure), invertebrates (e.g., Corophium volutator, 10-day exposure), and (72-hour ). Due to its high molecular weight and insolubility, PVPP does not bioaccumulate in food chains, further reducing potential long-term ecological harm. For disposal, is the preferred method, converting PVPP to and with minimal ash residue, aligning with standard practices for synthetic polymers. Landfilling is an alternative, where the stable, non-leaching nature of PVPP prevents contamination, though it contributes to long-term volume. Recycling initiatives, such as reusing spent PVPP up to four times in wine fining, offer a sustainable pathway to reduce disposal needs. As a vegan alternative to animal-derived fining agents like , PVPP use indirectly mitigates waste from animal processing. The (EFSA) has noted no safety concerns at typical use levels, supporting its low environmental risk profile under regulated applications.

Regulatory Status

In the United States, (PVPP) is regulated by the (FDA) as a secondary direct under 21 CFR 173.50, permitting its safe use as a in the production of and other malt beverages, removed by filtration to ensure no significant residues remain. Additionally, (PVP), a related , is authorized as an indirect in materials under 21 CFR 177.1680, where it functions as a component in articles intended for contact with . In the , PVPP is approved as the E 1202, authorized for use in beverages such as wine, beer, and fruit juices at levels, meaning as much as technologically required without exceeding good manufacturing practices. The (EFSA) re-evaluated E 1202 in 2020, concluding that its use as a does not raise safety concerns at reported levels of exposure, with no need for a numerical (ADI). For pharmaceutical applications, PVPP, known as crospovidone, is included in the United States Pharmacopeia-National Formulary (USP-NF) , which specifies standards for its identity, purity, and performance as a tablet disintegrant and binder. The International Council for Harmonisation (ICH) guideline Q3C addresses residual solvents in pharmaceutical excipients like crospovidone, establishing permissible daily exposure limits for solvents such as N-methylpyrrolidone to control impurities. Internationally, the Joint FAO/WHO Expert Committee on Food Additives (JECFA) has evaluated PVPP and assigned no numerical ADI, indicating its safety for use in food without specified limits, based on evaluations from 1983. Under standards, aligned with International Organisation of Vine and Wine (OIV) practices, PVPP is permitted for fining wine at maximum addition rates of 80 g/hL to remove polyphenols. Regarding labeling, PVPP is not classified as a major food under regulations like the 's Regulation (EU) No 1169/2011 or the U.S. Food Allergen Labeling and Act, so declaration is not required unless cross-contamination risks apply in specific products. As a synthetic derived from non-animal sources, PVPP qualifies for vegan in beverages, with organizations like Vegan Action confirming its compliance when used in certified formulations. Since the 2020 EFSA re-evaluation, no new regulatory restrictions on PVPP have been imposed globally, though its potential use in nanomaterial forms is subject to ongoing monitoring under frameworks like the EU's REACH regulation for nanoforms, which requires specific registration since 2020.

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