Aichemical

Hamay CL 2839
Hoja Tecnica
STRUCTURAL FORMULA CAS Number:

Polyfunctional aziridine crosslinker

2011
[64265-57-2]

CH3
MOLECULAR FORMULA: C24H41N3O6

CH3 - CH2 - C - CH2 - O - CO - CH2 - CH2 - N

MOLECULAR WEIGHT: 467.60

3
SPECIFICATIONS AND PROPERTIES
Appearance Solubility Identification IR Spectrum Refractive index Viscosity Water tolerance PI content : Matches with standard. : 1.4690 - 1.4730 (25C). : 100 300 Cp (25C). : Not less than 100%. : < 100 ppm. : Clear yellowish liquid with amine-like odour. : Soluble in water.

APPLICATIONS AND USES

Adhesives Coatings Leather and textile Printing inks Crosslinking

STABILITY AND STORAGE

Material in itself is normally stable, but can become unstable at elevated temperatures and pressures.

TOXICITY AND SAFETY

Route RTE Oral Organism ORGN rat Dose DOSE LD50 3.038 mg/kg

PACKAGING

25 or 200 kg metallic drums and 800 or 1000 kg plastic containers.

Aichemical

Ruta 25 KM 3.5 CP: 1629 Pilar, Buenos Aires

info@aichemical.com.ar

Formula Molecular weight Monomer Monomer Content (meq/g) Monomer Functionality Density @ 25 C (g/ml) Viscosity, (cp @ 25C) Vapor pressure (mm Hg) Freezing point (C) Appearance Solubility

C24H35O6N3 461 PI 5.4-6.6 ~2.8 1.05-1.09 100-500 <0.1 <-15 Slight amber clear liquid 2.5-5 % water

Polyfunctional Aziridine is a propylene imine tri-functional polyaziridine that is used in both aqueous and non-aqueous coatings, inks and adhesives. Polyfunctional aziridine is miscible with water, acetone, methanol, chloroform and benzene.

Molecule

Polyfunctional aziridine is used as low energetic crosslinker and adhesion promotor. This compound is very reactive with materials containing active hydrogens, that is carboxylated polymers. This allows the polyfunctional aziridine to be incorporated in a variety of systems. When used as a crosslinker, the polyfunctional aziridine imparts flexibility, improves solvent resistance, water and alcohol resistance, increases hardness and dramatically upgrade adhesion of solvent and waterborne polymers.

Polyfunctional Aziridina dramatically improves adhesion of polymer systems to difficult substrates, that is to polyolefins, polyester, glass and many other difficult substrates. It can also be used as primer acting as a tie-coat to improve the adhesion of the polymer system to various substrates. The proper conditions for incorporating must be determined with each individual system with success being judged by the performance of the coating.

The key variables are: 1. 2. 3. 4. 5. Method of addition. pH (for aqueous systems) or the availability of a proton scource. Level of aziridine. Initial temperature. Time of addition.

Effective utilization of aziridine chemistry is very much dependent on the availability of an active proton in order to protonate the aziridine ring. Unlike many other products used to crosslink polymers, temperature is not a major factor in the use of aziridine chemistry. Control of the availability of a proton is the key factor. The most common method used to protonate the aziridine ring is the reaction with a carboxylic functionality in the backbone of the polymer system. Other functionalities like secondary amino groups and mercaptanes can be used as well. The trifunctional aziridine discussed here can perform as adhesion enhancers and crosslinkers in carboxylated polymers at low or room temperatures. Aziridine chemistry can effectively be used by the coatings industry in two major ways: A. B. Adhesion promotion Crosslinking (Curing).

A. - Adhesion Promotion. The use of a polyfunctional aziridine solely for adhesion promotion is generally limited to carboxylated latex systems (emulsions). 1. Method of addition The aziridines are post add to a finished latex. They are not added during the polymerization and they are not added to the compound coating. They are added during the cool down cycle after pH adjustment and with good agitation. The compound may be added neat or diluted in water (or another non protonating water compatible solvent). 2. pH of latex A pH of 7.0-7.5 at the time of addition often produces the best results. This will vary between individual systems, test runs at different pHs should reveal the optimum pH. 3. Level of aziridine used Increase of the aziridine level used, does not necessarily improve the desired effect and may even cause a decrease in performance. Evaluating several levels in the range of 0.5-2.0 parts per 100 parts of polymer solid is recommended. 4. Temperature at time of addition Ambient temperatures have been thoroughly explored and are known to give satisfactorily results. Addition at elevated temperatures (say 40C) during the cool down cycle better utilizes the aziridine and causes the reaction to go to completion in a very short time. 5. Time of addition The aziridines can be added either during the cool down cycle, after the completion of the polymerization process or at some time later (before compounding to a finished coating). If added during the cool down cycle, the reaction will go very rapidly towards completion. If added later, after the cooling is completed, agitation should be continued for about 24-36 hours before the polymer system is compounded into a finished coating. The incorporation of the polyfunctional aziridine into a latex system does not for the most part affect or alter the physical properties of the polymer system, like the viscosity, Tg, gloss etc. B.- Cross-linking Mechanism For crosslinking the aziridines have utility in both organic and aqueous (dispersion) coating systems. Also they may be applied in latex (emulsion) systems. To function, an acidic site must be available to protonate the aziridine ring.

This active group should be in the polymer backbone and is most commonly a carboxylic group. The make up of the backbone structure itself (be it acrylic, vinyl acrylic, vinyl acetate, urethane, styrene acrylic etc ) is of little influence on the crosslinking reaction. Necessary is the presence of an acidic site. The crosslinking mechanism is outlined in the figure below:

Carboxyl Group

Aziridine

Croos-Link Network

The use of polyfunctional aziridine discussed here to crosslink coating systems will: 1. 2. 3. 4. 5. 6. 7. 8. reduce blocking improve flexibility improve stain resistance increase hardness increase water, alcohol and solvent resistance improve adhesion to polyester, poly olefins, poly vinyl chlorides, aluminium, steel and glass. Reduce energy costs Increase line speeds.

For the crosslinking application the compound is added to the finished compounded coating just prior to use. At this point the acidic groups have little opportunity to react with the aziridine groups. A low boiling and volatile amine may be added to reduce the chance of a premature reaction even further. The mixed system now has a pot life of about 18-36 hours. In non emulsion (latex) systems a thickening or gel formation will occur over time. In an emulsion system there will be loss of the aziridine functionality. If needed this loss can be replenished at a later time. Typical crosslinking conditions are: 1. Method of addition: The aziridine can be added directly to the compound coating system just prior to use. The aziridine is added slowly under good agitation and may be added neat or in solution. In the latter case a non protic solution should be used. 2. pH of the system: A system (aqueous) of pH 9.0-9.5 often produces the most optimum results. Systems with a lower pH will allow premature reaction of the aziridine functionality and require therefore higher concentrations in order to achieve the same end point. Non emulsion aqueous systems will show more formation of gel at lower pH levels.

Organic solvent systems with to too low levels of a volatile amine will also show gel formation.

3. Level of aziridine used: The amount of polyfunctional aziridine used will depend on the desired properties of the finished coating. 4. Initial temperature: As a general rule it is best to add the polyfunctional aziridine to the system at ambient temperature. 5. Addition time: The polyfunctional aziridines should be added just prior to use and not during the manufacture or storage of the coating system.

Solubility Aziridine is miscible in water and many common organic solvents like acetone, methanol, chloroform and benzene. This allow it to be used in both aqueous and solvent systems.

Compatibility Aziridine is very reactive with active hydrogen groups, such as those found in carboxyl groups of acrylic emulsions and polyurethane dispersions. Do not expose to acidic materials, high heat, direct sunlight, ultraviolet radiation and strong oxidizers.

Safety The polymer produced by the homopolymerization of the polyfunctional aziridine is very resistant to most solvents. Every effort therefore should be made in order to keep equipment clean and avoid such homopolymerization. For data regarding regulations and toxicity, please refer to the respective Safety Data Sheets. Process benefits Application Adhesives Benefits Increases cohesive strength Faster cure time Improving adhesion to difficult substrates (polyolefins, marble, stainless steel, glass) Increases cohesive strength Adhesion modification Faster cure time Improving adhesion to difficult substrates (polyolefins, marble, stainless steel, glass) Improves adhesion to various substrates Increase of scuff resistance Increase of water and chemical resistance Faster cure time Improves adhesion to various substrates Increase scuff resistance Increase water and chemical resistance Increase high temperature resistance Faster cure time Improves water and chemical resistance Faster cure time Low VOC formulations Improves black heal resistance Improves abrasion resistance Improves wear resistance Faster cure time Increases water and chemical resistance Adhesion modification Faster cure time Improves adhesion Increases anti-static properties Increases anti-static properties Increases anti-blocking properties Improves adhesion of coatings.

Pressure sensitive adhesives

Printing Inks

Over-print varnishes

Wood coatings

Leather and textile coatings Protective films Photographic film Plastic films