Quick Search
Polyaziridine (Polyethylenimine) is a polymer with repeating units composed of the amine group and two carbon aliphatic CH2CH2 spacers.
Linear polyethyleneimines contain all secondary amines, in contrast to branched Polyaziridine (Polyethylenimine)s which contain primary, secondary and tertiary amino groups.
Totally branched, dendrimeric forms were also reported.
CAS: 9002-98-6
MF: C2H5N
MW: 43.07
EINECS: 618-346-1
Synonyms
POLYETHYLENEIMINE, BRANCHED;Aziridine,homopolymer;Ethyleneimine,homopolymer;polyethylenimine(10,000);polyethylenimine(20,000);PEI-1750;PEI-2500;ETHYLENE IMINE POLYMER SOLUTION, 50% IN WATER
Polyaziridine (Polyethylenimine) is produced on an industrial scale and finds many applications usually derived from its polycationic character.
Polyaziridine (Polyethylenimine), an organic polyamine polymer, is one of the most prominent examples of cationic polymers capable of gene transfection in vitro and in vivo into various cell lines and tissues.
Polyaziridine (Polyethylenimine) was also applied in different fields from gene therapy and several studies have emphasized the importance of this polymer in medicinal chemistry.
Polyaziridine (Polyethylenimine) is a saturated organic heteromonocyclic parent, a member of aziridines and an azacycloalkane.
Polyaziridine (Polyethylenimine) has a role as an alkylating agent.
Polyaziridine (Polyethylenimine) is a conjugate base of an aziridinium.
All Polyaziridine (Polyethylenimine) polymers are hydrophilic and may contain approx.
30% hydrated water.
Polyaziridine (Polyethylenimine) is a water-soluble polymer that has been used in the treatment of bowel disease.
Polyaziridine (Polyethylenimine) has a receptor activity and can be used as a surfactant, which is an agent that reduces surface tension.
Polyaziridine (Polyethylenimine) can also be used as a polymer with a pyrazole ring, which is an aromatic heterocycle containing two nitrogen atoms and two carbon atoms.
Polyaziridine (Polyethylenimine) has been shown to have biochemical properties such as being biocompatible and exhibiting antifungal properties.
Polyaziridine (Polyethylenimine) can be synthesized by reacting ethyleneimine and aziridine.
This polymer is biocompatible, water-soluble, and can be synthesized using ethyleneimine and aziridine.
Polyaziridine (Polyethylenimine)'s synthesis involves reacting ethyleneimine with aziridine to form the imine intermediate followed by hydrolysis of the imine to form polyethyleneimine.
Polyaziridine (Polyethylenimine) is a surfactant that acts as a polyelectrolyte multilayer on a charged surface, providing that surface with a biocompatible coat.
Polyaziridine (Polyethylenimine) is a hydrophilic cationic polymer widely used as a nonviral nucleotide delivery reagent.
Polyaziridine (Polyethylenimine) can be used as a non-viral synthetic polymer vector for in vivo delivery of therapeutic nucleic acids.
The interaction between negatively charged nucleic acids and positively charged polymer backbone results in the formation of nano-sized complexes.
This neutralized complex protects the enclosed nucleic acid from enzymes and maintains its stability till the cellular uptake takes place.
For example, human serum albumin conjugated Polyaziridine (Polyethylenimine) shows good pDNA transfection and low toxicity.
Polyaziridine (Polyethylenimine) can be used to functionalize single-walled nanotubes (SWNTs) to improve their solubility and biocompatibility while maintaining the structural integrity of the original SWNT.
Covalently functionalized SWNTs find application in CO2 absorption and gene delivery.
Polyaziridine (Polyethylenimine) Chemical Properties
Melting point: 59-60°C
Boiling point: 250 °C(lit.)
Density: 1.030 g/mL at 25 °C
Vapor pressure: 9 mmHg ( 20 °C)
Refractive index: n20/D 1.5290
Fp: >230 °F
Storage temp.: 2-8°C
Solubility: DMSO (Sparingly)
Form: Liquid
Color: Pale yellow
Specific Gravity: 1.045 (20/4℃)
PH: pH(50g/l, 25℃) : 10～12
Water Solubility: Soluble in water.
Sensitive: Hygroscopic
InChI: InChI=1S/C2H5N/c1-2-3-1/h3H,1-2H2
InChIKey: NOWKCMXCCJGMRR-UHFFFAOYSA-N
LogP: -0.969 (est)
EPA Substance Registry System: Polyaziridine (Polyethylenimine) (9002-98-6)
The linear Polyaziridine (Polyethylenimine) is a semi-crystalline solid at room temperature while branched Polyaziridine (Polyethylenimine) is a fully amorphous polymer existing as a liquid at all molecular weights.
Polyaziridine (Polyethylenimine) is soluble in hot water, at low pH, in methanol, ethanol, or chloroform.
Polyaziridine (Polyethylenimine) is insoluble in cold water, benzene, ethyl ether, and acetone.
Polyaziridine (Polyethylenimine) has a melting point of around 67 °C.
Both linear and branched Polyaziridine (Polyethylenimine) can be stored at room temperature.
Polyaziridine (Polyethylenimine) is able to form cryogels upon freezing and subsequent thawing of its aqueous solutions.
Uses
Polyaziridine (Polyethylenimine) acts as a protein precipitant used to purify proteins.
Polyaziridine (Polyethylenimine) is used as a chelating agent and as a scavenger for aldehydes and oxides.
Polyaziridine (Polyethylenimine) is also used in detergents, paper industry, dyes, printing inks and in water treatment.
Polyaziridine (Polyethylenimine) is widely used in many applications due to its polycationic character.
Unlike its linear equivalent, branched Polyaziridine (Polyethylenimine) contains primary, secondary, and tertiary amines.
Primarily utilized in industrial applications, high molecular weight Polyaziridine (Polyethylenimine) has been used as a flocculating agent, textile coating, adhesion promoter, enzyme carrier, and as a material for CO2 capture.
Polyethyleneimine is used as a polyelectrolyte multilayer on charged surfaces to provide a biocompatible coating on surfaces.1Detergents, adhesives, water treatment, printing inks, dyes, cosmetics, and paper industry, adhesion promoter, lamination primer, fixative agent, flocculant, cationic dispersant, stability enhancer, surface activator, chelating agent, scavenger for aldehydes and oxides.
Polyaziridine (Polyethylenimine) can be used as a non-viral synthetic polymer carrier for in vivo delivery of therapeutic nucleic acids.
The interaction between the negatively charged nucleic acid and the positively charged polymer backbone leads to the formation of nanoscale complexes.
Polyaziridine (Polyethylenimine) neutralising complex protects the enclosed nucleic acid from enzymes and maintains its stability until cellular uptake occurs.
For example, human serum albumin-coupled Polyaziridine (Polyethylenimine) shows good pDNA transfection and low toxicity.
Polyaziridine (Polyethylenimine) can be used to functionalize single-walled nanotubes (SWNTs) to improve their solubility and biocompatibility while maintaining the structural integrity of the original SWNT.
Covalently functionalized SWNTs can be used for CO2 uptake and gene delivery.
Branched Polyaziridine (Polyethylenimine) can also be used to modify the surface properties of adsorbents.
Polyaziridine (Polyethylenimine)-modified aqueous zirconia/PAN nanofibres have a high fluoride adsorption capacity and a wide working pH range, and can therefore be used for groundwater defluoridation.
The degree of polymerization used in the paper industry is about 1 00.
Polyaziridine (Polyethylenimine) has high reaction activity, can react with the hydroxyl group in cellulose and cross-linking polymerization, so that the wet strength of the paper.
The presence of any acid, base, and aluminum sulfate will affect the wet strength and retention.
As the wet strength agent of the respiratory paper without sizing, the retention agent and the beating agent in the paper making process can reduce the beating degree of the pulp, improve the dehydration ability of the paper, and speed up the drainage of the pulp, the fine fibers in white water are easy to flocculate.
Polyaziridine (Polyethylenimine) can also be used to treat cellophane, reduce wetting deformation of the paper, etc.
Polyaziridine (Polyethylenimine) can also be used for fiber modification, printing and dyeing auxiliaries, ion exchange resins, etc.
Polyaziridine (Polyethylenimine) has a strong binding force to acid dyes and can be used as a fixing agent for acid dye dyeing paper.
Polyaziridine (Polyethylenimine) finds many applications in products like: detergents, adhesives, water treatment agents and cosmetics.
Owing to its ability to modify the surface of cellulose fibres, Polyaziridine (Polyethylenimine) is employed as a wet-strength agent in the paper-making process.
Polyaziridine (Polyethylenimine) is also used as flocculating agent with silica sols and as a chelating agent with the ability to complex metal ions such as zinc and zirconium.
There are also other highly specialized Polyaziridine (Polyethylenimine) applications:
Biology
Polyaziridine (Polyethylenimine) has a number of uses in laboratory biology, especially tissue culture, but is also toxic to cells if used in excess.
Toxicity is by two different mechanisms, the disruption of the cell membrane leading to necrotic cell death (immediate) and disruption of the mitochondrial membrane after internalisation leading to apoptosis (delayed).
Attachment promoter
Polyethyleneimines are used in the cell culture of weakly anchoring cells to increase attachment.
Polyaziridine (Polyethylenimine) is a cationic polymer; the negatively charged outer surfaces of cells are attracted to dishes coated in Polyaziridine (Polyethylenimine), facilitating stronger attachments between the cells and the plate.
Transfection reagent
Polyaziridine (Polyethylenimine) was the second polymeric transfection agent discovered, after poly-L-lysine.
Polyaziridine (Polyethylenimine) condenses DNA into positively charged particles, which bind to anionic cell surface residues and are brought into the cell via endocytosis.
Once inside the cell, protonation of the amines results in an influx of counter-ions and a lowering of the osmotic potential.
Osmotic swelling results and bursts the vesicle releasing the polymer-DNA complex (polyplex) into the cytoplasm.
If the polyplex unpacks then the DNA is free to diffuse to the nucleus.
Permeabilization of gram negative bacteria
Poly(ethylenimine) is also an effective permeabilizer of the outer membrane of Gram-negative bacteria.
Production Methods
Polyaziridine (Polyethylenimine) is produced by the homopolymerization of ethylenimine.
The reaction is catalyzed by acids, Lewisacids, or haloalkanes.
The polymerization is usually carried out at 90 – 110 ℃ in water or in a variety of organic solvents.
The average molecular mass of the polyethylenimine prepared as described above is 10 000 – 20 000.
Higher molecular mass polymers are prepared by addition of a difunctional alkylating agent, such as chloromethyloxirane or 1,2-dichloroethane.
Polyaziridine (Polyethylenimine) with a higher average molecular mass can also be provided by ultrafiltration of polymers with a broad mass distribution.
Likewise, polymers of lower molecular mass can be obtained by inclusion of a low molecular mass amine, such as 1,2- ethanediamine, during polymerization.
By using these techniques a range of molecular masses from 300 to 10 6 can be obtained.
Cross-linking during the polymerization of ethylenimine in organic solvents leads to solid polyethylenimines.
Furthermore the polymerization process can be conducted on the surface of organic or inorganic materials, thus fixing the polyethylenimines to a support.
Synthesis
Branched Polyaziridine (Polyethylenimine) can be synthesized by the ring opening polymerization of aziridine.
Depending on the reaction conditions different degree of branching can be achieved.
Linear Polyaziridine (Polyethylenimine) is available by post-modification of other polymers like poly(2-oxazolines) or N-substituted polyaziridines.
Linear Polyaziridine (Polyethylenimine) was synthesised by the hydrolysis of poly(2-ethyl-2-oxazoline) and sold as jetPEI.
The current generation in-vivo-jet Polyaziridine (Polyethylenimine) uses bespoke poly(2-ethyl-2-oxazoline) polymers as precursors.
