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VINYLPYRROLIDONE-VINYL ACETATE

Vinylpyrrolidone-vinyl acetate, an analog of povidone, is used as a tablet binder, a film-former, and as part of the matrix material used in controlled-release formulations.
In tableting, Vinylpyrrolidone-vinyl acetate can be used as a binder for direct compression and as a binder in wet granulation.
Vinylpyrrolidone-vinyl acetate provides good adhesion, elasticity, and hardness, and can be used as a moisture barrier.

CAS Number: 25086-89-9
EC Number: 607-540-1
Molecular Formula: C6H9NO.C4H6O2
Molecular Weight: 197.23

Synonyms: Poly(1-vinylpyrrolidone-co-vinyl Acetate), Polectron 845, Luviskol Va 28i, Luviskol Va 37e, Luviskol Va 64, Kolima 10, Kolima 35, Ethenyl Acetate;1-ethenylpyrrolidin-2-one, Gantron S 860, Pvp-va, Ganex E 535, Vinyl Acetate-vinylpyrrolidone Copolymer, Vinylpyrrolidinone-vinyl Acetate Copolymer, Gaf-s 630, Vinyl Acetate-vinylpyrrolidone Polymer, Vinylpyrrolidinone-vinyl Acetate Polymer, Vinylpyrrolidone-vinyl Acetate Copolymer, N-vinylpyrrolidone-vinyl Acetate Polymer, Vinyl Acetate-n-vinylpyrrolidone Polymer, Vinyl Acetate-vinylpyrrolidinone Copolymer, Vinyl Acetate-n-vinylpyrrolidinone Polymer, Vinyl Acetate-n-vinylpyrrolidone Copolymer, Acetic Acid Vinyl Ester, Polymer With 1-vinyl-2-pyrrolidinone, Acetic Acid Ethenyl Ester, Polymer With 1-ethenyl-2-pyrrolidinone, Vinyl Acetate-n-vinylpyrrolidinone Copolymer, I 535, I 635, I 735, S 630, 1-vinyl-2-pyrrolidone-vinyl Acetate Copolymer, Vinyl Acetate-1-vinyl-2-pyrrolidinone Polymer, Vinyl Acetate-n-vinyl-2-pyrrolidone Copolymer, Vinyl Acetate-n-vinyl-2-pyrrolidinone Copolymer, Ethenyl Acetate, Polymer With 1-ethenyl-2-pyrrolidinone, Mfcd00134018, Acetic Acid Ethenyl Ester, Polymer With 1-ethenyl-2-pyrrolidinoneother Ca Index Names:2-pyrrolidinone, 1-ethenyl-, Polymer With Ethenyl Acetate, 2-pyrrolidinone, Polymer With Ethenyl Acetate, Luviskol Va-64, Vinyl Acetate N-vinyl-pyrrolidone Polymer, Schembl29127, Copovidone (technical Grade), Vinylpyrrolidone/vinyl Acetate, Vinyl Pyrrolidone/vinyl Acetate, N-vinylpyrrolidone/vinyl Acetate, 1-vinylpyrrolidone Vinyl Acetate, Bcp31918, Nsc114023, Nsc114024, Nsc114025, Nsc114026, Akos015898247, Nsc-114023, Nsc-114024, Nsc-114025, Nsc-114026, Poly(1-vinylpyrrolidone-co-vinylacetate), Vinyl Acetate-vinyl Pyrrolidone Copolymer, 1-ethenylpyrrolidin-2-one; Ethenyl Acetate, Ethenyl Ethanoate; 1-ethenylpyrrolidin-2-one, Ft-0659810, A817635, Acetic Acid Ethenyl Ester; 1-ethenyl-2-pyrrolidinone, Poly(1-vinylpyrrolidone-co-vinyl Acetate);polectron 845;luviskol Va 28i, Poly(1-vinylpyrrolidone - Vinyl Acetate) (copolymer, 7:3) (50% In Ethanol), Poly(1-vinylpyrrolidone-co-vinyl Acetate) (copolymer, 3:7) (50% In Ethanol), 733045-73-3, Copolyvidone, Vinylpyrrolidone-vinyl acetate copolymer, Copolymer of 1-vinyl-2-pyrrolidone and vinyl acetate in a ratio of 3:2 by mass, Poly (1-vinylpyrrolidone-co-vinyl acetate), Polyvinylpyrrolidone-vinyl Acetate Copolymer, PVP/VA, PVP/VA Copolymer, Kollidon VA 64, Plasdone® Crospovidone

Vinylpyrrolidone-vinyl acetate used as dry binder in tablets, as matrix formers for amorphous solid dispersions
Vinylpyrrolidone-vinyl acetate is a white or slightly yellowish, free-flowing powder with a faint characteristic odor and practically no taste.
Vinylpyrrolidone-vinyl acetate readily dissolves in all hydrophilic solvents.

Solutions of more than 10 % concentration can be prepared in water, ethanol, isopropanol, methylene chloride, glycerol and propylene glycol.
Vinylpyrrolidone-vinyl acetate is less soluble in ether, cyclic, aliphatic and alicyclic hydrocarbons.

Vinylpyrrolidone-vinyl acetate is copolymer that is soluble both in water and in alcohol.
Vinylpyrrolidone-vinyl acetate is used as a dry binder in tabletting, as a granulating auxiliary and as a film-forming agent in the pharmaceutical industry.

Vinylpyrrolidone-vinyl acetate is often added to coating solutions as a film-forming agent.
Vinylpyrrolidone-vinyl acetate provides good adhesion, elasticity, and hardness, and can be used as a moisture barrier.

Vinylpyrrolidone-vinyl acetate has better plasticity than povidone as a tablet binder, is less hygroscopic, more elastic, and better for film-forming applications than povidone.
Vinylpyrrolidone-vinyl acetate is also used in cosmetics as a thickener, dispersant, lubricant, film-forming agent and binder.
Vinylpyrrolidone-vinyl acetate is widely used in the food, cosmetic and pharmaceutical industry.

Vinylpyrrolidone-vinyl acetate is generally regarded as nontoxic.
However, oral consumption of excessive quantities may produce stomach upset.

Vinylpyrrolidone-vinyl acetate has not been shown to be sensitizing to the skin.
Animal studies in rats and dogs do not show significant toxicity with high dietary levels.

The average molecular weight of Vinylpyrrolidone-vinyl acetate is usually expressed as a K-value and Vinylpyrrolidone-vinyl acetate ranges between 45 and 70.

Vinylpyrrolidone-vinyl acetate is a synthetic random copolymer of 1-vinyl-2-pyrrolidone and viny acetate.
Vinylpyrrolidone-vinyl acetate is obtained by free-radical polymerisation of 6 parts of vinylpyrrolidone and 4 parts of vinyl acetate.
Vinylpyrrolidone-vinyl acetate is supplied in fine particle form and appears as a white to yellowish powder with a faint taste and odour.

Vinylpyrrolidone-vinyl acetate is used as a binder, hardener, a film-former, and as part of a proprietary blend used in controlled-release formulations of tablets and other products.
In tableting, Vinylpyrrolidone-vinyl acetate can be used as a binder for direct compression of tablets, increasing their hardness and as a binder in wet granulation of tablets.

Vinylpyrrolidone-vinyl acetate is a copolymer of 1-vinyl-2-pyrrolidone and vinyl acetate obtained by free-radical polymerization of 6 parts of vinylpyrrolidone with 3 parts of vinyl acetate to produce a water-soluble polymer.
Vinylpyrrolidone-vinyl acetate is typically spray-dried and supplied in a relatively fine particle size.
Vinylpyrrolidone-vinyl acetate has a faint taste and occurs as a white to yellowish-white amorphous powder.

Vinylpyrrolidone-vinyl acetate is co-polymer made by N-vinyl-2- pyrolidone and vinyl acetate.
Vinylpyrrolidone-vinyl acetate is used for coating agent or binder. Vinylpyrrolidone-vinyl acetate is insoluble in water, so dimethyl formamide (DMF) was used as the eluent.

In this application, Even though DMF is used as the eluent, adding lithium bromide into the eluent is effective.
Lithium bromide was added for analyzing Vinylpyrrolidone-vinyl acetate.

Vinylpyrrolidone-vinyl acetate can be used as an excipient, such as Film formers, adhesives, etc.
Pharmaceutical excipients, or pharmaceutical auxiliaries, refer to other chemical substances used in the pharmaceutical process other than pharmaceutical ingredients.

Pharmaceutical excipients generally refer to inactive ingredients in pharmaceutical preparations, which can improve the stability, solubility and processability of pharmaceutical preparations.
Pharmaceutical excipients also affect the absorption, distribution, metabolism, and elimination (ADME) processes of co-administered drugs.

Vinylpyrrolidone-vinyl acetate is acetic acid ethenyl ester polymer with 1-etheny1-2 pyrrolidinone.
Vinylpyrrolidone-vinyl acetate is a synthetic random copolymer of 1-vinyl-2-pyrrolidone and vinyl acetate in a ratio (by weight) of 6:3.
In the USP-NF and Ph.Eur Vinylpyrrolidone-vinyl acetate is defined as a copolymer of 1-ethenylpyrrolidin-2-one and ethenyl acetate in the mass proportion of 3:2.

Vinylpyrrolidone-vinyl acetate is an analogue of Povidone, and corresponds to the general chemical formula shown below:
(C6H9NO)n (C4H6O2)m (111.1)n + (86.1)m (the ratio of n to m is approximately n = 1.2m).

Vinylpyrrolidone-vinyl acetate’s (average) molecular weight is usually expressed as a K-value.
The K-value of Kollidon VA 64 is nominally 28, with a range of 25.2-30.8 while the K-value for Plasdone S 630 is specified to be between 25.4 and 34.2. K-values are calculated from the kinematic viscosity of a 1% aqueous solution.

From this information, the molecular weight can be calculated using the formula below:
M = 22.22 (K + 0.075K2)1.65.

Vinylpyrrolidone-vinyl acetate, together with the other polyvinylpyrrolidone polymers (e.g Povidone and Crospovidone) are some of the many materials that were first commercialised by BASF in the early 1930s as part of the company’s acetylene chemistry programme (started and led by the chemist, Walter Reppe).
Over the course of several decades, Pyrrolidones have been adapted and applied across multiple fields, including pharmaceuticals, cosmetics, and food owing to versatility, solubility and consistency in their many performance attributes.

The method used to synthesise Vinylpyrrolidone-vinyl acetate is very much similar to that used by Povidone, that is, the Reppe process is used to produce Polyvinylpyrrolidone, which is then copolymerised with Vinyl acetate.
However, as the Vinyl acetate is insoluble in water the reaction is carried out in an organic solvent rather than water.

The presence of Vinyl acetate in the molecule renders Vinylpyrrolidone-vinyl acetate more hydrophobic compared with Povidone and also makes its films less brittle.
Indeed, Vinylpyrrolidone-vinyl acetate was the desire to improve upon Povidone’s technological attributes that motivated the development of povidone derivatives.

Compared with Povidone, Vinylpyrrolidone-vinyl acetate is more versatile as an excipient.
Vinylpyrrolidone-vinyl acetate also exhibits greater plasticity and gives granules and powder mixtures flexibility to deform thereby reducing tendencies to undergo capping and lamination during tabletting.
Vinylpyrrolidone-vinyl acetate is supplied as a white to white-yellow amorphous, finely divided powder.

Vinylpyrrolidone-vinyl acetate Market Snapshot (2022-2032):
The global Vinylpyrrolidone-vinyl acetate market is estimated to register remarkable growth, expanding at a CAGR of around 9% to 10% during the forecast period 2022-2032.
Increasing demand for non-toxic, and pharmaceutically inactive thickening and binding agents across diverse industries is expected to accelerate the sales of Vinylpyrrolidone-vinyl acetate in the global market.

Vinylpyrrolidone-vinyl acetate is an analog of povidone which is commonly used as a fining agent, tablet binder, emulsifier, and a part of matrix materials in controlled-release formulations.
Vinylpyrrolidone-vinyl acetate is increasingly used as an alternative to povidone, owing to its less hygroscopic, more elastic, and better plasticity attributes in comparison to povidone.

Vinylpyrrolidone-vinyl acetate is gaining huge traction as a film-forming agent and is being added to the coating solutions for enhancing its adhesion, elasticity, and hardness.
Vinylpyrrolidone-vinyl acetate is finding a wide range of applications across various sectors such as industrial, ceramics, adhesives, battery, and others, on account of several benefits, Vinylpyrrolidone-vinyl acetate offers over other polymers.
This is projected to accelerate the sales of Vinylpyrrolidone-vinyl acetate in the global market.

Applications of Vinylpyrrolidone-vinyl acetate:

Applications in Pharmaceutical Formulations or Technology:
Vinylpyrrolidone-vinyl acetate was developed as an improvement over Povidone (binder).
Vinylpyrrolidone-vinyl acetate favourable technical properties, namely better flowability, lower hygroscopicity, spherical particle shape, plasticity, lower glass-transition temperature, and hydrophobic–hydrophilic balance, rendered Vinylpyrrolidone-vinyl acetate highly advantageous in direct compression and roller-compaction tabletting operations.
While Vinylpyrrolidone-vinyl acetate is still used as a dry binder (for direct compression and roller compression), Vinylpyrrolidone-vinyl acetate's main utility is as a matrix former for the development of solid dispersions, film former (especially in the formulation of moisture-barrier coatings), and as a matrice former for sustained-release solid dosage forms.

Binder in Tablets:
Vinylpyrrolidone-vinyl acetate performs superbly as a dry binder for direct compression applications.
Vinylpyrrolidone-vinyl acetate is particularly preferred for formulations susceptible to capping due to its plasticity.

Finer grades have demonstrated superior binding performance compared with either Povidone and Cellulose-based polymers.
Formulations developed with Vinylpyrrolidone-vinyl acetate show a direct relationship between tablet hardness, friability, porosity and disintegration with the applied compaction force.

Binder in Wet Granulation:
The high solubility of Vinylpyrrolidone-vinyl acetate in water and standard granulation liquids makes Vinylpyrrolidone-vinyl acetate as an ideal binder in wet granulation operations.
Vinylpyrrolidone-vinyl acetate may be added either as a solution or in the form of a dry powder followed by the addition of the granulating solvent or a combination of both.
Vinylpyrrolidone-vinyl acetate, owing to its low hygroscopicity, allows greater predictable granulation endpoints and its granules have a much less propensity to stick to tooling, even when conducted under less favourable conditions.

Roller Compression:
Vinylpyrrolidone-vinyl acetate has been shown to be particularly well-suited for use in roller compaction.
Vinylpyrrolidone-vinyl acetate is an excipient of choice when particle size distribution and particle shape considerations are critical during roller compression process design.
Owing to its spherical shape and fine size Vinylpyrrolidone-vinyl acetate gives better surface coverage and develops multiple bridges that lead to hard tablets with a reduced friability.

Film-Coating Film Former:
Vinylpyrrolidone-vinyl acetate is a film former and it soluble membranes whose solubility is independent of pH.
Vinylpyrrolidone-vinyl acetate films are also less hygroscopic, but more flexible compared with those formed by Povidone.

For best results, it’s used in combination with other film-forming polymers that are less hygroscopic.
Due to Vinylpyrrolidone-vinyl acetate's flexibility, a plasticizer is not required.

Polymer for Amorphous Solid Dispersions:
Vinylpyrrolidone-vinyl acetate is a suitable polymer for developing amorphous solid dispersions that are both kinetically and thermodynamically stable.
Both spray-drying and hot melt extrusion approaches can be reliably used.

Other Uses:
Inhibition of crystallisation of APIs in liquid soft-gel formulations
Sugar coating applications (to improve adhesion)
Subcoating of tablets (film coating)

Benefits of Vinylpyrrolidone-vinyl acetate:
Vinylpyrrolidone-vinyl acetate provides erodible instant release matrix
Vinylpyrrolidone-vinyl acetate is a solubilizer, dispersant, crystallization inhibitor and matrix former

For direct compression, roller compaction and wet granulation, suitable for markets with higher humidity exposure
Vinylpyrrolidone-vinyl acetate has excellent stability throughout the extrusion process

A coarse powder provides a dust free handling, good flowability and faster extruder feeding
Recently obtained GRAS/SA status (Generally Recognized As Safe/Self-Affirmed) by the U.S. Food & Drug Administration (FDA) for use in food and nutritional supplements e.g. vitamin and mineral tablets

Molecular Weight of Vinylpyrrolidone-vinyl acetate:
Molecular weights of 45,000-70,000 have been determined for Koliidon VA 64.
The average molecular weight of Vinylpyrrolidone-vinyl acetate is usually expressed as a K-value.

The K-value of Kollidon VA 64 is nominally 28, with a range of 25.2-30.8.
The K-value of Plasdone S 630 is specified between 25.4 and 34.2. K-values are calculated from the kinematic viscosity of a 1% aqueous.

Molecular weight can be calculated with the formula
M = 22.22 (K + 0.075K2)1.65

The Ph.Eur and USP-NF describe Vinylpyrrolidone-vinyl acetate as a copolymer of 1-ethenylpyrrolidin-2-one and ethenyl acetate in the ratio (by mass) of 3:2

Handling and Storage of Vinylpyrrolidone-vinyl acetate:
Precautions for safe handling:
Avoid inhalation of vapour or mist.

Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage.

Storage class (TRGS 510):
8A: Combustible, corrosive hazardous materials

Stability and Reactivity of Vinylpyrrolidone-vinyl acetate:

Chemical stability:
Stable under recommended storage conditions.

Incompatible materials:

Strong oxidizing agents:

Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions.
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.

First Aid Measures of Vinylpyrrolidone-vinyl acetate:

General advice:
Consult a physician.
Show this safety data sheet to the doctor in attendance.

Move out of dangerous area:

If inhaled:
If breathed in, move person into fresh air.
If not breathing, give artificial respiration.
Consult a physician.

In case of skin contact:
Take off contaminated clothing and shoes immediately.
Wash off with soap and plenty of water.
Consult a physician.

In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.

If swallowed:
Do NOT induce vomiting.
Never give anything by mouth to an unconscious person.

Rinse mouth with water.
Consult a physician.

Firefighting Measures of Vinylpyrrolidone-vinyl acetate:

Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas

Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.

Accidental Release Measures of Vinylpyrrolidone-vinyl acetate:

Personal precautions, protective equipment and emergency procedures:
Use personal protective equipment.

Avoid breathing vapours, mist or gas.
Evacuate personnel to safe areas.

Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.

Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste.
Keep in suitable, closed containers for disposal.

Identifiers of Vinylpyrrolidone-vinyl acetate:
Chemical Name: Acetic acid ethenyl ester, polymer with 1-etheny1-2 pyrrolidinone
CAS Registry Number: [25086-89-9]
Empirical Formula: (C6H9NO)n (C4H6O2)m (111.1)n + (86.1)m - The ratio of n to m is approximately n = 1.2m
EINECS Number: 607-540-1
FDA UNII Code: D9C330MD8B

Synonyms: Poly(1-vinylpyrrolidone-co-vinyl acetate)
CAS Number: 25086-89-9

Product Code: EPY0002138
CAS Number: 25086-89-9
Molecular Formula: C6H9NO.C4H6O2
Molecular Weight: 197.23

Properties of Vinylpyrrolidone-vinyl acetate:
Physical form: Solid, powder
Appearance: White, cream to yellowish finely divided powder
pH value: 3.0-7.0
pKa: -1.4 (Computed)
Log P: -1.1
Bulk density: Standard grades: 0.20-0.30 g/ml
Fine grades: 0.08-0.15 g/ml

Tapped density: Standard grades: 0.30-0.45 g/ml
Density (true): 1.1 g/ml
Flashpoint: 215 0C
Flowability: Poorly flowing to relatively free-flowing powder
Glass transition temperature: 100 – 110 0C
Hygroscopicity: Absorbs <10% weight at 50% RH
K-value -630: Dependent on the supplier/grade. For Plasdone®, K value = 25 – 35
Melting point: 140 0C
Solubility: Soluble in water (179g/l). Soluble in ethanol, isopropyl alcohol, propylene glycol and glycerol (a 10% w/w solution can be easily prepared)
Viscosity (Brookfield): Viscosity of aqueous solutions varies with concentration and molecular weight of the polymer. A 5% w/v solution has a viscosity of 4-5 mPas (25 oC)

Molecular Weight: 197.23 g/mol
Molecular Formula: C10H15NO3
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 3
Rotatable Bond Count: 3
Exact Mass: 197.10519334 g/mol
Monoisotopic Mass: 197.10519334 g/mol
Topological Polar Surface Area: 46.6 Å²
Heavy Atom Count: 14
Complexity: 186
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently Bonded Unit Count: 2

MeSH of Vinylpyrrolidone-vinyl acetate:
Kollidon Va64
Poly(v-co-v-ac)
Poly(vinyl Pyrrolidone-co-vinyl Acetate)
Poly(vinylpyrrolidone-co-vinyl-acetate)
Polyvidone-vinylacetate 64
Pvp Va64
Pvp-va
Pvpva 64