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admin 4月 7th, 2025 News

Bis[2-(N,N-Dimethylaminoethyl)] Ether: A Catalyst for Accelerated Curing in Industrial Coatings

Abstract:

Bis[2-(N,N-Dimethylaminoethyl)] ether (BDMAEE), also known as Jeffcat ZF-20 or Dabco BL-19, is a tertiary amine catalyst widely employed in the formulation of polyurethane, epoxy, and other thermosetting industrial coatings. Its primary function is to accelerate the curing process, leading to enhanced productivity, improved coating properties, and reduced energy consumption. This article delves into the chemical properties, mechanism of action, applications, advantages, disadvantages, safety considerations, and future trends of BDMAEE in the context of industrial coatings, highlighting its critical role in modern coating technology.

Table of Contents:

Introduction
Chemical Properties
- 2.1 Chemical Formula and Structure
- 2.2 Physical Properties
- 2.3 Reactivity
Mechanism of Action in Coating Systems
- 3.1 Polyurethane Coatings
- 3.2 Epoxy Coatings
- 3.3 Other Thermosetting Coatings
Applications in Industrial Coatings
- 4.1 Automotive Coatings
- 4.2 Coil Coatings
- 4.3 Wood Coatings
- 4.4 Marine Coatings
- 4.5 Protective Coatings
Advantages of Using BDMAEE
- 5.1 Accelerated Curing Time
- 5.2 Improved Throughput
- 5.3 Enhanced Coating Properties
- 5.4 Lower Energy Consumption
Disadvantages and Limitations
- 6.1 Volatility and Odor
- 6.2 Potential for Yellowing
- 6.3 Compatibility Issues
- 6.4 Over-Catalyzation
Safety Considerations
- 7.1 Toxicity
- 7.2 Handling and Storage
- 7.3 Environmental Impact
Formulation Considerations
- 8.1 Dosage
- 8.2 Compatibility with other Additives
- 8.3 Influence of Temperature and Humidity
Alternative Catalysts
- 9.1 Other Tertiary Amines
- 9.2 Metal Catalysts
- 9.3 Amine Blocking Agents
Future Trends and Developments
Conclusion
References

1. Introduction

Industrial coatings play a crucial role in protecting and enhancing the performance of a wide range of materials, from automobiles and buildings to appliances and machinery. The curing process, during which the liquid coating transforms into a solid film, is a critical step in achieving the desired protective and aesthetic properties. The duration of this curing process significantly impacts production efficiency and overall cost-effectiveness. Catalysts are often employed to accelerate the curing reaction, thereby reducing processing time and improving throughput. Bis[2-(N,N-Dimethylaminoethyl)] ether (BDMAEE) has emerged as a prominent catalyst in various industrial coating formulations due to its effectiveness in promoting rapid curing, particularly in polyurethane and epoxy systems. This article provides a comprehensive overview of BDMAEE, exploring its chemical properties, mechanism of action, applications, advantages, disadvantages, safety considerations, and future trends in the industrial coatings sector.

2. Chemical Properties

2.1 Chemical Formula and Structure

BDMAEE is an organic compound belonging to the class of tertiary amines. Its chemical formula is C₁₀H₂₄N₂O, and its structural formula can be represented as:

(CH₃)₂N-CH₂-CH₂-O-CH₂-CH₂-N(CH₃)₂

The molecule contains two dimethylaminoethyl groups linked by an ether linkage. This structure contributes to its strong catalytic activity, particularly in reactions involving isocyanates and epoxides.

2.2 Physical Properties

The physical properties of BDMAEE are summarized in the following table:

Property	Value	Unit
Molecular Weight	172.31	g/mol
Appearance	Colorless to slightly yellow liquid	–
Boiling Point	189-192	°C
Flash Point	60-70	°C
Density	0.84-0.86	g/cm³
Viscosity	2-3	cP (at 25°C)
Refractive Index	1.44-1.45	–
Solubility	Soluble in water and organic solvents	–

2.3 Reactivity

BDMAEE is a highly reactive tertiary amine. The nitrogen atoms in the molecule possess lone pairs of electrons, making it a strong nucleophile and a good base. This reactivity enables it to catalyze various chemical reactions, including:

Polyurethane formation: BDMAEE accelerates the reaction between isocyanates and alcohols (polyols) to form polyurethanes.
Epoxy curing: BDMAEE can catalyze the ring-opening polymerization of epoxy resins with curing agents (hardeners) like amines or anhydrides.
Other reactions: BDMAEE can also catalyze other reactions, such as transesterification and Michael addition.

3. Mechanism of Action in Coating Systems

The catalytic activity of BDMAEE in coating systems stems from its ability to facilitate the reactions between the key components, leading to the formation of the crosslinked polymer network that constitutes the cured coating.

3.1 Polyurethane Coatings

In polyurethane coatings, BDMAEE primarily acts as a catalyst for two crucial reactions:

The reaction between isocyanate and polyol: BDMAEE promotes the nucleophilic attack of the hydroxyl group of the polyol on the electrophilic carbon atom of the isocyanate group, forming a urethane linkage. The proposed mechanism involves the amine nitrogen coordinating with the hydroxyl group, increasing its nucleophilicity.
The isocyanate trimerization reaction: BDMAEE can also catalyze the trimerization of isocyanates, leading to the formation of isocyanurate rings. These rings contribute to the crosslink density and thermal stability of the polyurethane coating.

The relative rates of these two reactions are influenced by the concentration of BDMAEE, the reaction temperature, and the specific isocyanate and polyol being used. Optimizing these parameters is crucial for achieving the desired coating properties.

3.2 Epoxy Coatings

In epoxy coatings, BDMAEE functions as an accelerator for the reaction between the epoxy resin and the curing agent (hardener), typically an amine or an anhydride.

Amine-cured epoxy systems: BDMAEE enhances the nucleophilic attack of the amine curing agent on the epoxy ring, leading to ring-opening polymerization and crosslinking. The amine group of the curing agent abstracts a proton from the BDMAEE, creating a more reactive nucleophile.
Anhydride-cured epoxy systems: While less common, BDMAEE can also promote the reaction between epoxy resins and anhydrides. In this case, BDMAEE facilitates the ring-opening of the anhydride by the hydroxyl groups generated during the epoxy-anhydride reaction.

The choice of curing agent and the concentration of BDMAEE are critical factors in determining the curing rate and final properties of the epoxy coating.

3.3 Other Thermosetting Coatings

BDMAEE can also be used as a catalyst in other thermosetting coating systems, such as those based on acrylic resins, alkyd resins, and unsaturated polyesters. Its catalytic activity in these systems depends on the specific chemistry involved and the presence of reactive functional groups that can interact with the amine nitrogen of BDMAEE.

4. Applications in Industrial Coatings

BDMAEE finds widespread application in various industrial coating sectors due to its effectiveness in accelerating curing and improving coating performance.

4.1 Automotive Coatings

In automotive coatings, BDMAEE is used in both primer and topcoat formulations, particularly in polyurethane-based systems. It helps to reduce the curing time of the coatings, allowing for faster production cycles in automotive assembly plants. The use of BDMAEE also contributes to improved coating hardness, scratch resistance, and gloss.

4.2 Coil Coatings

Coil coatings are applied to continuous metal strips that are subsequently formed into various products, such as appliance panels, roofing sheets, and automotive parts. BDMAEE is used in coil coating formulations to ensure rapid curing during the high-speed coating process. The accelerated curing enables high production rates and minimizes the risk of coating defects.

4.3 Wood Coatings

Wood coatings are used to protect and enhance the aesthetic appeal of wood furniture, flooring, and other wood products. BDMAEE is employed in polyurethane wood coatings to shorten the curing time and improve the coating’s resistance to abrasion, chemicals, and moisture.

4.4 Marine Coatings

Marine coatings are designed to protect ships, offshore platforms, and other marine structures from corrosion and fouling. BDMAEE is used in marine coatings based on epoxy and polyurethane resins to accelerate curing and provide durable protection against harsh marine environments.

4.5 Protective Coatings

Protective coatings are applied to a wide range of industrial equipment and infrastructure to prevent corrosion, abrasion, and chemical attack. BDMAEE is used in these coatings to enhance the curing speed and provide long-lasting protection in demanding environments. Examples include coatings for pipelines, storage tanks, and bridges.

Coating Type	Application Area	Resin System	Benefits from BDMAEE Use
Automotive Coating	Car bodies, parts	Polyurethane, Acrylic	Faster curing, improved hardness & scratch resistance, enhanced gloss
Coil Coating	Metal sheets (appliances, roofing)	Polyurethane, Polyester	Rapid curing at high speeds, minimized defects, increased production efficiency
Wood Coating	Furniture, flooring	Polyurethane	Shortened curing time, improved abrasion & chemical resistance, enhanced moisture resistance
Marine Coating	Ships, offshore platforms	Epoxy, Polyurethane	Accelerated curing, durable protection against corrosion & fouling in harsh marine environments
Protective Coating	Pipelines, tanks, bridges	Epoxy, Polyurethane	Enhanced curing speed, long-lasting protection in demanding industrial environments

5. Advantages of Using BDMAEE

The use of BDMAEE in industrial coating formulations offers several significant advantages:

5.1 Accelerated Curing Time

The primary advantage of BDMAEE is its ability to significantly reduce the curing time of coatings. This acceleration is crucial for improving production efficiency and minimizing downtime.

5.2 Improved Throughput

By reducing the curing time, BDMAEE enables higher throughput in coating operations. This increased throughput translates into higher productivity and reduced manufacturing costs.

5.3 Enhanced Coating Properties

In many cases, the use of BDMAEE can also lead to improved coating properties, such as hardness, gloss, chemical resistance, and adhesion. These improvements are often attributed to the more complete and uniform curing achieved with the catalyst.

5.4 Lower Energy Consumption

In some coating processes, the curing step requires elevated temperatures. By accelerating the curing process, BDMAEE can reduce the energy required to heat the coatings, leading to lower energy consumption and reduced environmental impact.

6. Disadvantages and Limitations

Despite its numerous advantages, BDMAEE also has some disadvantages and limitations that need to be considered when formulating industrial coatings:

6.1 Volatility and Odor

BDMAEE is a volatile compound with a characteristic amine odor. This odor can be unpleasant and may require the use of ventilation systems to maintain acceptable air quality in the workplace. The volatility of BDMAEE can also lead to its gradual loss from the coating formulation, potentially affecting the long-term performance of the coating.

6.2 Potential for Yellowing

In some cases, the use of BDMAEE can contribute to yellowing of the coating, particularly upon exposure to UV light. This yellowing can be undesirable, especially in coatings that are intended to be clear or white.

6.3 Compatibility Issues

BDMAEE may not be compatible with all coating formulations. It can react with certain components or interfere with other additives, leading to undesirable effects such as gelling, precipitation, or reduced coating performance.

6.4 Over-Catalyzation

Using too much BDMAEE can lead to over-catalyzation, which can result in rapid and uncontrolled curing, leading to defects such as blistering, cracking, or poor adhesion.

7. Safety Considerations

BDMAEE is a chemical substance that requires careful handling and storage to ensure the safety of workers and the environment.

7.1 Toxicity

BDMAEE is considered to be moderately toxic. It can cause skin and eye irritation upon contact. Inhalation of vapors can cause respiratory irritation. Ingestion can cause gastrointestinal distress. Appropriate personal protective equipment (PPE), such as gloves, goggles, and respirators, should be used when handling BDMAEE.

7.2 Handling and Storage

BDMAEE should be handled in a well-ventilated area. It should be stored in tightly closed containers in a cool, dry place away from heat, sparks, and open flames. Contact with incompatible materials, such as strong acids and oxidizing agents, should be avoided.

7.3 Environmental Impact

BDMAEE can be harmful to aquatic organisms. Spills should be contained and cleaned up immediately. Waste containing BDMAEE should be disposed of in accordance with local regulations.

8. Formulation Considerations

Effective use of BDMAEE in coating formulations requires careful consideration of several factors:

8.1 Dosage

The optimal dosage of BDMAEE depends on the specific coating formulation, the desired curing rate, and the desired coating properties. Typically, BDMAEE is used at concentrations ranging from 0.1% to 2% by weight of the resin solids. Excessive use can lead to the disadvantages mentioned earlier.

8.2 Compatibility with other Additives

It is essential to ensure that BDMAEE is compatible with all other additives in the coating formulation, such as pigments, fillers, stabilizers, and flow control agents. Incompatibility can lead to phase separation, sedimentation, or other undesirable effects.

8.3 Influence of Temperature and Humidity

The curing rate of coatings catalyzed by BDMAEE is influenced by temperature and humidity. Higher temperatures generally accelerate the curing process, while high humidity can sometimes inhibit the curing reaction, particularly in polyurethane systems.

9. Alternative Catalysts

While BDMAEE is a widely used catalyst, alternative catalysts are available for industrial coating applications.

9.1 Other Tertiary Amines

Other tertiary amines, such as triethylamine (TEA), triethylenediamine (TEDA), and N,N-dimethylcyclohexylamine (DMCHA), can also be used as catalysts in coating formulations. However, these amines may have different catalytic activities and may affect the coating properties differently.

9.2 Metal Catalysts

Metal catalysts, such as tin compounds (e.g., dibutyltin dilaurate, DBTDL), zinc compounds, and bismuth compounds, are also commonly used in polyurethane coatings. Metal catalysts are generally more active than tertiary amines, but they can also be more toxic and can contribute to yellowing.

9.3 Amine Blocking Agents

Amine blocking agents can be used to temporarily deactivate BDMAEE or other amine catalysts, allowing for longer pot life of the coating formulation. The blocking agent is typically a compound that reacts with the amine nitrogen, rendering it unreactive. The blocking agent can be removed by heating or by reaction with another component of the coating formulation, thereby reactivating the amine catalyst.

Catalyst Type	Examples	Advantages	Disadvantages
Tertiary Amines	TEA, TEDA, DMCHA	Lower toxicity compared to metal catalysts, readily available	Lower catalytic activity compared to metal catalysts, potential for amine odor
Metal Catalysts	DBTDL, Zinc compounds, Bismuth compounds	High catalytic activity, can lead to fast curing	Higher toxicity, potential for yellowing, can affect coating stability
Amine Blocking Agents	Ketimines, Aldimines	Extended pot life, controlled curing	Requires a deblocking step, can affect coating properties if not completely removed

10. Future Trends and Developments

The future of BDMAEE in industrial coatings is likely to be shaped by several trends and developments:

Development of Low-Odor BDMAEE Derivatives: Research efforts are focused on developing BDMAEE derivatives with lower volatility and reduced odor, addressing a major drawback of the current product.
Combination with other Catalysts: Synergistic catalyst systems combining BDMAEE with other catalysts, such as metal catalysts or enzymes, are being explored to achieve optimal curing performance and coating properties.
Microencapsulation of BDMAEE: Encapsulating BDMAEE in microcapsules can provide controlled release of the catalyst, allowing for improved control over the curing process and extended pot life of the coating formulation.
Bio-based Alternatives: There is growing interest in developing bio-based alternatives to BDMAEE, derived from renewable resources. This would contribute to more sustainable coating formulations.
Further Optimization of Dosage & Compatibility: Research continues to optimize the dosage of BDMAEE for specific applications and to improve its compatibility with a wider range of coating components.

11. Conclusion

Bis[2-(N,N-Dimethylaminoethyl)] ether (BDMAEE) remains a vital catalyst in the industrial coatings industry, particularly in polyurethane and epoxy systems. Its ability to accelerate curing, improve throughput, and enhance coating properties makes it a valuable tool for formulators. While its volatility, odor, and potential for yellowing pose challenges, ongoing research and development efforts are focused on mitigating these drawbacks and exploring new applications. The future of BDMAEE in industrial coatings is likely to involve the development of lower-odor derivatives, synergistic catalyst systems, microencapsulation techniques, and bio-based alternatives, contributing to more sustainable and high-performance coating solutions.

12. References

Wicks, D. A., Jones, F. N., & Pappas, S. P. (2007). Organic Coatings: Science and Technology. John Wiley & Sons.
Lambourne, R., & Strivens, T. A. (1999). Paint and Surface Coatings: Theory and Practice. Woodhead Publishing.
Ashby, J., & Goode, R. J. (2001). High Solids Alkyd Resins. John Wiley & Sons.
Ulrich, H. (1996). Introduction to Industrial Polymers. Hanser Gardner Publications.
Römpp Online, Georg Thieme Verlag. (Chemical database; search for "Bis(2-dimethylaminoethyl) ether").
Database of REACH registered substances, European Chemicals Agency. (Search for "Bis(2-dimethylaminoethyl) ether").
Randall, D., & Lee, S. (2002). The Polyurethanes Book. John Wiley & Sons.
Primeaux, D. J., & Lindsly, C. (1996). US Patent 5508344. Method of reducing odor in amine catalysts.
Blank, W.J. (1982). Progress in Organic Coatings, 10(3), 255-271. The Chemistry of Amine Catalyzed Epoxy Resins.
Bauer, D. R., & Dickie, R. A. (1980). Journal of Coatings Technology, 52(660), 63-67. Amine-epoxy cure kinetics.

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admin 4月 7th, 2025 News

Bis[2-(N,N-Dimethylaminoethyl)] Ether (BDMAEE) in Sustainable Wood Composite Bonding Solutions

Introduction

The wood composite industry is facing increasing pressure to adopt more sustainable practices. Traditional formaldehyde-based resins, while providing excellent bonding properties, release harmful volatile organic compounds (VOCs) during manufacturing and use, contributing to air pollution and health concerns. This has spurred research into alternative, bio-based adhesives and innovative bonding technologies. Bis[2-(N,N-Dimethylaminoethyl)] ether (BDMAEE), also known as 2,2′-Dimorpholinyldiethyl Ether, is emerging as a promising component in sustainable wood composite bonding solutions due to its catalytic properties and potential to reduce or eliminate formaldehyde emissions. This article provides a comprehensive overview of BDMAEE, exploring its properties, mechanisms of action, applications in wood composite bonding, and its role in promoting sustainable manufacturing practices.

1. Overview of BDMAEE

Bis[2-(N,N-Dimethylaminoethyl)] ether (BDMAEE) is a tertiary amine catalyst commonly used in polyurethane (PU) foam production. Its molecular structure features two tertiary amine groups connected by an ether linkage. This structure contributes to its high catalytic activity and its ability to accelerate various chemical reactions relevant to wood composite bonding.

1.1 Nomenclature and Identification

Property	Value
IUPAC Name	2,2′-Dimorpholinyldiethyl Ether
CAS Registry Number	6425-39-4
Molecular Formula	C??H??N?O
Molecular Weight	214.35 g/mol
Other Names	Bis(2-dimethylaminoethyl) ether; BDMAEE

1.2 Physical and Chemical Properties

Property	Value	Source
Appearance	Colorless to slightly yellow liquid	Supplier Data Sheet
Density	0.85 g/cm³ at 20°C	Supplier Data Sheet
Boiling Point	189-192°C	Supplier Data Sheet
Flash Point	68°C	Supplier Data Sheet
Vapor Pressure	Low	Supplier Data Sheet
Solubility in Water	Soluble	Supplier Data Sheet
pH (1% aqueous solution)	Alkaline	Supplier Data Sheet

1.3 Production Methods

BDMAEE is typically synthesized through the ethoxylation of dimethylamine followed by etherification. The specific manufacturing process is often proprietary but generally involves reacting dimethylamine with ethylene oxide to form 2-(dimethylamino)ethanol, which is then etherified to produce BDMAEE.

2. Mechanism of Action in Wood Composite Bonding

BDMAEE’s role in wood composite bonding stems primarily from its catalytic activity in various chemical reactions, particularly those involving crosslinking and curing of adhesives.

2.1 Catalysis of Polyurethane Formation

BDMAEE is a well-established catalyst for polyurethane (PU) foam production. In wood composite applications involving PU adhesives, BDMAEE accelerates the reaction between isocyanates and polyols, leading to the formation of urethane linkages. This enhanced reaction rate results in faster curing times and improved bond strength.

The mechanism involves BDMAEE acting as a nucleophile, abstracting a proton from the hydroxyl group of the polyol. This activated polyol then attacks the isocyanate group, forming the urethane linkage. BDMAEE is regenerated in the process, allowing it to catalyze further reactions.

2.2 Promotion of Crosslinking in Bio-Based Resins

Beyond PU adhesives, BDMAEE can also promote crosslinking in other bio-based resins, such as those derived from lignin, tannins, or carbohydrates. The mechanism varies depending on the specific resin system, but generally involves BDMAEE facilitating reactions that lead to the formation of covalent bonds between resin molecules, thereby increasing the network density and improving the mechanical properties of the adhesive.

For example, in lignin-based adhesives, BDMAEE can catalyze the reaction of lignin with crosslinking agents such as glyoxal or epichlorohydrin, promoting the formation of a rigid, three-dimensional network.

2.3 pH Modification and Its Impact on Bonding

BDMAEE is an alkaline compound. Its addition to adhesive formulations can modify the pH of the mixture. This pH adjustment can be crucial for the activation of certain crosslinking agents or for improving the compatibility of different components within the adhesive system.

For instance, in some tannin-based adhesives, a slightly alkaline pH is required for the tannins to react effectively with formaldehyde or other crosslinking agents. BDMAEE can provide the necessary alkalinity without contributing to formaldehyde emissions.

3. Applications in Wood Composite Bonding

BDMAEE is finding increasing use in various wood composite bonding applications, particularly where sustainability and reduced formaldehyde emissions are desired.

3.1 Particleboard and Fiberboard Manufacturing

Traditional particleboard and fiberboard production relies heavily on formaldehyde-based resins, such as urea-formaldehyde (UF) and phenol-formaldehyde (PF). BDMAEE can be used as a catalyst or co-catalyst in alternative resin systems to reduce or eliminate formaldehyde emissions.

Formaldehyde-Free Resins: BDMAEE can catalyze the crosslinking of bio-based resins, such as those derived from soy protein, starch, or lignin, to produce formaldehyde-free particleboard and fiberboard.
Low-Formaldehyde Resins: In modified UF or PF resin systems, BDMAEE can be used to reduce the amount of formaldehyde required while maintaining acceptable bonding performance. This can be achieved by promoting more efficient crosslinking of the resin.

3.2 Plywood Production

Plywood manufacturing also traditionally utilizes formaldehyde-based resins. BDMAEE can be employed in similar ways as in particleboard and fiberboard production to promote the use of more sustainable adhesives.

Tannin-Formaldehyde Resins: BDMAEE can be used to adjust the pH of tannin-formaldehyde resin systems, optimizing the reaction between tannins and formaldehyde and reducing the amount of free formaldehyde in the final product.
Bio-Based Plywood Adhesives: BDMAEE can catalyze the crosslinking of bio-based polymers, such as modified starch or soy protein, to create formaldehyde-free plywood adhesives.

3.3 Laminated Veneer Lumber (LVL) and Glued Laminated Timber (Glulam)

LVL and Glulam are engineered wood products that require high-strength adhesives to bond multiple layers of wood veneer or timber. BDMAEE can be used in both PU and bio-based adhesive systems for LVL and Glulam production.

Polyurethane Adhesives for LVL and Glulam: BDMAEE accelerates the curing of PU adhesives, leading to faster production cycles and improved bond strength in LVL and Glulam products.
Lignin-Based Adhesives for LVL: BDMAEE can be used in conjunction with other crosslinking agents to create high-performance lignin-based adhesives for LVL production.

3.4 Wood Adhesives for General Applications

Beyond composite manufacturing, BDMAEE can also be incorporated into wood adhesives for general applications, such as furniture assembly and woodworking.

Improved Bonding of Difficult-to-Bond Wood Species: BDMAEE can enhance the bonding of wood species that are typically difficult to bond due to their high oil or resin content.
Faster Curing Times: The catalytic activity of BDMAEE can significantly reduce the curing time of wood adhesives, improving productivity.

4. Advantages of Using BDMAEE in Wood Composite Bonding

The use of BDMAEE in wood composite bonding offers several advantages over traditional approaches.

4.1 Reduced Formaldehyde Emissions

The primary advantage is the potential to reduce or eliminate formaldehyde emissions from wood composite products. By enabling the use of formaldehyde-free or low-formaldehyde resins, BDMAEE contributes to improved indoor air quality and reduced health risks.

4.2 Enhanced Bond Strength

BDMAEE can enhance the bond strength of adhesives by promoting more efficient crosslinking and improved adhesion to the wood substrate.

4.3 Faster Curing Times

The catalytic activity of BDMAEE can significantly reduce the curing time of adhesives, leading to faster production cycles and increased throughput.

4.4 Improved Sustainability

By enabling the use of bio-based resins, BDMAEE contributes to the overall sustainability of wood composite products, reducing reliance on fossil fuels and promoting the use of renewable resources.

4.5 Versatility

BDMAEE can be used in a variety of adhesive systems, including PU, lignin-based, tannin-based, and starch-based adhesives, making it a versatile tool for wood composite bonding.

5. Potential Drawbacks and Mitigation Strategies

While BDMAEE offers numerous advantages, there are also potential drawbacks that need to be considered.

5.1 Potential Toxicity and Handling Precautions

BDMAEE is a tertiary amine and can be irritating to the skin, eyes, and respiratory system. Proper handling precautions, including the use of personal protective equipment (PPE), such as gloves, safety glasses, and respirators, are essential.

5.2 Influence on Adhesive Viscosity and Rheology

The addition of BDMAEE can affect the viscosity and rheology of adhesive formulations. Careful formulation adjustments may be necessary to ensure that the adhesive has the desired application properties.

5.3 Potential for Yellowing of Adhesive

In some cases, BDMAEE can contribute to the yellowing of adhesive formulations, particularly when exposed to UV light. The use of UV stabilizers or alternative catalysts may be necessary to mitigate this effect.

5.4 Odor

BDMAEE possesses a characteristic amine odor, which some may find objectionable. Proper ventilation during manufacturing and application is recommended.

Mitigation Strategies:

Proper Ventilation: Ensure adequate ventilation in manufacturing facilities to minimize exposure to BDMAEE vapors.
Personal Protective Equipment (PPE): Require workers to wear appropriate PPE, including gloves, safety glasses, and respirators.
Formulation Optimization: Carefully optimize adhesive formulations to minimize the amount of BDMAEE required and to address any potential issues with viscosity, rheology, or color.
Alternative Catalysts: Explore the use of alternative catalysts that may offer similar performance with fewer drawbacks.
UV Stabilizers: Incorporate UV stabilizers into adhesive formulations to prevent yellowing.

6. Regulatory Considerations

The use of BDMAEE in wood composite bonding is subject to various regulatory requirements.

6.1 VOC Emissions Regulations

Wood composite products are often subject to regulations limiting VOC emissions, including formaldehyde. The use of BDMAEE to reduce or eliminate formaldehyde emissions can help manufacturers comply with these regulations.

6.2 Chemical Substance Regulations (e.g., REACH, TSCA)

BDMAEE is subject to regulations governing the manufacture, import, and use of chemical substances, such as the European Union’s REACH (Registration, Evaluation, Authorisation and Restriction of Chemicals) regulation and the United States’ TSCA (Toxic Substances Control Act). Manufacturers and users must ensure that they comply with all applicable requirements.

6.3 Occupational Safety and Health Regulations

Occupational safety and health regulations govern the handling and use of chemicals in the workplace. Employers must provide workers with appropriate training and PPE to minimize the risk of exposure to BDMAEE.

7. Market Trends and Future Outlook

The market for sustainable wood composite bonding solutions is growing rapidly, driven by increasing demand for environmentally friendly products and stricter regulations on formaldehyde emissions. BDMAEE is well-positioned to play a significant role in this market.

7.1 Increasing Demand for Sustainable Wood Composites

Consumers and businesses are increasingly seeking out sustainable wood composite products that are made with environmentally friendly materials and processes. This trend is driving demand for adhesives that reduce or eliminate formaldehyde emissions.

7.2 Stricter Regulations on Formaldehyde Emissions

Government regulations on formaldehyde emissions are becoming increasingly stringent in many countries. This is forcing manufacturers to adopt alternative resin systems and bonding technologies that comply with these regulations.

7.3 Growth of Bio-Based Adhesives

The market for bio-based adhesives is growing rapidly as manufacturers seek to reduce their reliance on fossil fuels and promote the use of renewable resources. BDMAEE can play a key role in enabling the use of bio-based resins in wood composite bonding.

7.4 Innovation in Adhesive Technologies

Ongoing research and development efforts are focused on developing new and improved adhesive technologies that are both sustainable and high-performing. BDMAEE is likely to be a key component in many of these new technologies.

Future Outlook:

The future outlook for BDMAEE in wood composite bonding is positive. As demand for sustainable wood composite products continues to grow, and as regulations on formaldehyde emissions become more stringent, the use of BDMAEE is likely to increase. Further research and development efforts will likely focus on optimizing the use of BDMAEE in combination with bio-based resins and on developing new adhesive technologies that are both sustainable and high-performing.

8. Comparative Analysis with Alternative Catalysts

While BDMAEE is a valuable catalyst, it’s important to consider alternatives and their respective strengths and weaknesses.

Catalyst	Advantages	Disadvantages	Suitable Applications
BDMAEE	High catalytic activity, versatile, effective in various resin systems.	Potential for irritation, amine odor, possible yellowing.	Particleboard, fiberboard, plywood, LVL, Glulam, general wood adhesives.
Dabco (Triethylenediamine)	High catalytic activity, well-established, often used in PU foams.	Strong amine odor, potential for discoloration.	Polyurethane adhesives for wood bonding.
DMAPA (Dimethylaminopropylamine)	Good reactivity, lower molecular weight.	Strong amine odor, potential for irritation.	Wood adhesives requiring rapid curing.
Organic Acids (e.g., Citric Acid)	Less toxic, environmentally friendly.	Lower catalytic activity, may require higher concentrations.	Bio-based adhesives where toxicity is a major concern.
Metal Catalysts (e.g., Tin compounds)	High catalytic activity, effective in some PU systems.	Potential toxicity, environmental concerns, regulatory restrictions.	Specialized PU adhesives for high-performance applications.

9. Conclusion

Bis[2-(N,N-Dimethylaminoethyl)] ether (BDMAEE) is a valuable tool for promoting sustainability in the wood composite bonding industry. Its catalytic properties enable the use of formaldehyde-free or low-formaldehyde resins, leading to improved indoor air quality and reduced health risks. While potential drawbacks such as toxicity and odor need to be carefully managed through proper handling and formulation optimization, the benefits of BDMAEE in terms of enhanced bond strength, faster curing times, and improved sustainability make it a promising component in the future of wood composite bonding. As demand for sustainable wood products continues to grow, BDMAEE is poised to play a significant role in shaping the industry’s transition towards more environmentally friendly practices.

Literature Sources:

[1] Ashori, A. (2008). Wood–plastic composites as promising green-building materials. Bioresource Technology, 99(11), 4661-4667.

[2] Dunky, M. (1998). Urea-formaldehyde (UF) adhesives for wood. International Journal of Adhesion and Adhesives, 18(2), 95-106.

[3] Frihart, C. R., & Birkeland, M. (2015). Adhesives used for wood and wood products. Forest Products Laboratory, USDA Forest Service, General Technical Report FPL-GTR-238.

[4] Pizzi, A. (2003). Recent developments in bio-based adhesives for wood bonding: Opportunities and issues. Journal of Adhesion, 79(6), 477-492.

[5] Sellers, T. (2001). Wood adhesives: Chemistry and technology. CRC press.

[6] Umemura, K., Inoue, A., & Kawai, S. (2006). Development of formaldehyde-free particleboards bonded with powdered tannin adhesives. Journal of Wood Science, 52(4), 321-326.

[7] European Chemicals Agency (ECHA). REACH Database. [Note: Specific REACH registration information should be referenced here, but external links are prohibited]

[8] United States Environmental Protection Agency (EPA). Toxic Substances Control Act (TSCA). [Note: Specific TSCA information should be referenced here, but external links are prohibited]

[9] Supplier Safety Data Sheets (SDS) for BDMAEE. [Note: Referencing specific SDS sheets by manufacturer is acceptable, but external links are prohibited]

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admin 4月 7th, 2025 News

Bis[2-(N,N-Dimethylaminoethyl)] Ether (BDMAEE) in Low-Odor Epoxy Resin Formulations: A Comprehensive Overview

Introduction

Epoxy resins are widely used thermosetting polymers renowned for their excellent adhesive properties, chemical resistance, and mechanical strength. They find applications in diverse industries, including coatings, adhesives, composites, and electronics. However, a significant drawback of many epoxy resin formulations is the presence of volatile organic compounds (VOCs) and unpleasant odors, often stemming from the curing agents or accelerators used. These odors can pose health risks and environmental concerns, limiting their applicability in enclosed spaces and sensitive environments.

Bis[2-(N,N-Dimethylaminoethyl)] ether (BDMAEE), a tertiary amine catalyst, presents a compelling alternative for formulating low-odor epoxy resin systems. This article provides a comprehensive overview of BDMAEE, focusing on its properties, mechanism of action, advantages in reducing odor, applications, handling precautions, and future trends.

1. Chemical Identity and Physical Properties

BDMAEE is a tertiary amine catalyst belonging to the ether amine family. Its chemical structure, properties, and parameters are crucial for understanding its functionality in epoxy resin formulations.

Chemical Name: Bis[2-(N,N-Dimethylaminoethyl)] Ether
Synonyms: Dimorpholinodiethyl ether, DMDEE, JEFFCAT ZF-10, DABCO DME
CAS Registry Number: 3033-62-3
Chemical Formula: C??H??N?O
Molecular Weight: 214.35 g/mol

Table 1: Physical Properties of BDMAEE

Property	Value	Unit	Reference
Appearance	Colorless to Pale Yellow Liquid	–	[1]
Density (20°C)	0.85 – 0.86	g/cm³	[2]
Boiling Point	189-190	°C	[3]
Flash Point (Closed Cup)	71-74	°C	[4]
Viscosity (20°C)	2.5 – 3.5	cP	[2]
Refractive Index (n20/D)	1.440 – 1.445	–	[1]
Solubility (Water, 20°C)	Soluble	–	Internal Data
Amine Value	520-530	mg KOH/g	[2]

2. Mechanism of Action as an Epoxy Curing Accelerator

BDMAEE functions as a highly efficient tertiary amine catalyst in epoxy resin curing reactions. Its mechanism involves two primary pathways:

Anion Generation: BDMAEE facilitates the ring-opening polymerization of epoxy resins by abstracting a proton from hydroxyl groups present in the resin or a co-reactant (e.g., alcohol). This generates an alkoxide anion, a powerful nucleophile that attacks the epoxide ring, initiating chain propagation.
```
R-OH + BDMAEE <=> R-O- + BDMAEE-H+
```
Coordination Catalysis: BDMAEE can coordinate with the epoxide oxygen, activating the epoxide ring towards nucleophilic attack. This coordination weakens the C-O bond in the epoxide, making it more susceptible to reaction with nucleophiles such as hydroxyl groups or amines.
```
Epoxide + BDMAEE <=> [Epoxide---BDMAEE] (activated complex)
```

The synergistic effect of these two pathways makes BDMAEE a potent accelerator, enabling rapid curing even at relatively low concentrations. The ether linkage in BDMAEE enhances its flexibility and availability of the amine groups, contributing to its high catalytic activity.

3. Advantages of BDMAEE in Low-Odor Formulations

The primary advantage of BDMAEE lies in its ability to produce low-odor epoxy resin formulations compared to traditional amine curing agents, particularly those with lower molecular weights or higher volatility.

Reduced Volatility: BDMAEE has a relatively high molecular weight and lower vapor pressure compared to many conventional amine curing agents like diethylenetriamine (DETA) or triethylenetetramine (TETA). This lower volatility translates to reduced emissions of odorous amines during and after the curing process.
Improved Amine Blushing Resistance: Amine blushing is a phenomenon observed with amine-cured epoxy resins, especially under humid conditions. It involves the reaction of amine curing agents with atmospheric carbon dioxide and moisture, forming carbamates that appear as a white, hazy film on the surface. BDMAEE-cured systems exhibit improved resistance to amine blushing due to the catalyst’s lower reactivity towards atmospheric CO? and its efficient incorporation into the polymer network.
Faster Cure Rates: BDMAEE’s high catalytic activity allows for faster cure rates at lower concentrations. This reduces the overall exposure time to uncured resin and minimizes the potential for odor generation.
Enhanced Chemical Resistance: Properly formulated BDMAEE-cured epoxy resins exhibit excellent chemical resistance, similar to those cured with traditional amine curing agents. This is crucial for applications where the cured material will be exposed to harsh chemicals or solvents.

Table 2: Comparison of Odor and Volatility of Different Curing Agents

Curing Agent	Molecular Weight (g/mol)	Boiling Point (°C)	Odor Level (Subjective)	Volatility (Relative)
Diethylenetriamine (DETA)	103.17	207	Strong, Pungent	High
Triethylenetetramine (TETA)	146.23	277	Strong, Ammoniacal	Medium
Isophorone Diamine (IPDA)	170.30	247	Moderate, Amine-like	Medium
Bis[2-(N,N-Dimethylaminoethyl)] Ether (BDMAEE)	214.35	189-190	Mild, Amine-like	Low

Note: Odor Level is subjective and varies based on individual sensitivity. Volatility is a relative comparison.

4. Applications of BDMAEE in Epoxy Resin Formulations

BDMAEE finds applications in a wide array of epoxy resin formulations where low odor and rapid cure are desirable.

Coatings:
- Floor Coatings: BDMAEE is used in self-leveling epoxy floor coatings for residential, commercial, and industrial applications. The low-odor characteristic makes it suitable for use in occupied spaces.
- Protective Coatings: Used in protective coatings for metal structures, pipelines, and chemical storage tanks, offering excellent chemical resistance and corrosion protection with minimal odor.
- Waterborne Epoxy Coatings: BDMAEE can be incorporated into waterborne epoxy systems as a co-catalyst to enhance cure speed and film properties.
Adhesives:
- Structural Adhesives: Employed in structural adhesives for bonding metals, plastics, and composites in automotive, aerospace, and construction industries. The low-odor property is beneficial in enclosed manufacturing environments.
- Electronics Adhesives: Used in electronics assembly for bonding components to printed circuit boards (PCBs), providing good electrical insulation and mechanical strength.
Composites:
- Fiber-Reinforced Polymers (FRPs): Utilized in the manufacturing of FRP composites for aerospace, automotive, and marine applications. The faster cure rates facilitated by BDMAEE can improve production efficiency.
- Tooling Resins: Used in tooling resins for creating molds and patterns, offering good dimensional stability and heat resistance.
Encapsulation Compounds:
- Electronics Encapsulation: Used as a catalyst in epoxy formulations for encapsulating electronic components, providing protection against moisture, dust, and mechanical stress. The low-odor characteristic is important for worker safety and comfort in electronics manufacturing facilities.

5. Formulation Considerations and Optimization

Optimizing epoxy resin formulations with BDMAEE requires careful consideration of various factors, including resin type, hardener type, stoichiometry, and other additives.

Resin Selection: BDMAEE is compatible with a wide range of epoxy resins, including bisphenol-A epoxy resins, bisphenol-F epoxy resins, epoxy novolacs, and cycloaliphatic epoxy resins. The choice of resin depends on the specific application requirements, such as viscosity, glass transition temperature (Tg), and chemical resistance.
Hardener Selection: While BDMAEE primarily acts as an accelerator, it is typically used in conjunction with a primary amine or anhydride hardener. The type and amount of hardener significantly influence the cure rate, mechanical properties, and chemical resistance of the cured epoxy. Aliphatic amines, cycloaliphatic amines, and polyamidoamines are commonly used hardeners.
Stoichiometry: The stoichiometry of the epoxy resin and hardener should be carefully controlled to ensure complete curing and optimal properties. An excess or deficiency of either component can lead to incomplete curing, reduced mechanical strength, and increased odor.
Concentration of BDMAEE: The optimal concentration of BDMAEE typically ranges from 0.1% to 5% by weight of the resin-hardener mixture. The exact concentration depends on the desired cure rate and the reactivity of the resin and hardener. Higher concentrations of BDMAEE can accelerate the cure but may also reduce the pot life of the mixture.
Additives: Various additives can be incorporated into epoxy resin formulations to modify their properties, such as fillers, pigments, plasticizers, and flame retardants. Fillers can improve mechanical strength, reduce shrinkage, and lower cost. Pigments provide color and opacity. Plasticizers enhance flexibility. Flame retardants improve fire resistance.

Table 3: Example Epoxy Formulation with BDMAEE

Component	Weight (%)	Function
Bisphenol-A Epoxy Resin	50	Resin
Polyamidoamine Hardener	45	Hardener
BDMAEE	2.0	Accelerator
Fumed Silica	3.0	Thixotrope

6. Handling Precautions and Safety Information

BDMAEE, like other chemical compounds, should be handled with care. Following proper safety procedures is essential to minimize potential health risks.

Skin and Eye Contact: BDMAEE can cause skin and eye irritation. Wear appropriate personal protective equipment (PPE), such as gloves, safety glasses, and protective clothing, when handling the material. In case of skin contact, wash thoroughly with soap and water. In case of eye contact, flush with plenty of water for at least 15 minutes and seek medical attention.
Inhalation: Inhalation of BDMAEE vapors can cause respiratory irritation. Ensure adequate ventilation when working with the material. Use a respirator if necessary.
Ingestion: Do not ingest BDMAEE. If ingested, seek medical attention immediately.
Storage: Store BDMAEE in a cool, dry, and well-ventilated area away from incompatible materials, such as strong acids and oxidizing agents. Keep containers tightly closed to prevent moisture contamination.
Disposal: Dispose of BDMAEE and contaminated materials in accordance with local, state, and federal regulations.

7. Advantages and Disadvantages of Using BDMAEE

Table 4: Advantages and Disadvantages of BDMAEE

Feature	Advantages	Disadvantages
Odor	Lower odor compared to traditional amine curing agents	Still possesses a mild amine-like odor, may not be completely odorless.
Cure Rate	Faster cure rates at lower concentrations	May reduce pot life of the mixture.
Volatility	Lower volatility, reduced emissions
Blushing	Improved amine blushing resistance
Properties	Excellent chemical resistance and mechanical properties
Cost		Can be more expensive than some traditional amine curing agents.
Handling		Requires proper handling and safety precautions.

8. Alternatives to BDMAEE

While BDMAEE offers significant advantages in low-odor epoxy formulations, other catalysts and curing agents can be considered as alternatives, depending on the specific application requirements and cost constraints.

Modified Amines: Modified amines, such as Mannich bases and amidoamines, can provide lower odor and improved compatibility with epoxy resins.
Tertiary Amine Blends: Blends of tertiary amines with different functionalities can be used to optimize cure rate and odor profile.
Latent Catalysts: Latent catalysts, such as boron trifluoride complexes, require activation by heat or other stimuli, providing long pot life and controlled curing.
Anhydride Curing Agents: Anhydride curing agents offer good chemical resistance and electrical properties but typically require higher curing temperatures.

9. Market Trends and Future Outlook

The demand for low-VOC and low-odor epoxy resin formulations is steadily increasing due to growing environmental awareness and stricter regulations. This trend is driving the adoption of BDMAEE and other similar catalysts in various industries. Future research and development efforts are likely to focus on:

Developing novel catalysts with even lower odor and improved performance.
Optimizing epoxy resin formulations for specific applications.
Exploring new applications for BDMAEE in emerging fields, such as bio-based epoxy resins and sustainable coatings.
Improving the cost-effectiveness of BDMAEE to make it more competitive with traditional curing agents.

10. Conclusion

Bis[2-(N,N-Dimethylaminoethyl)] ether (BDMAEE) is a valuable tertiary amine catalyst for formulating low-odor epoxy resin systems. Its lower volatility, improved amine blushing resistance, and faster cure rates make it an attractive alternative to traditional amine curing agents in various applications, including coatings, adhesives, composites, and electronics. Careful formulation considerations, proper handling precautions, and ongoing research and development efforts will further enhance the performance and broaden the applicability of BDMAEE in the future. As environmental regulations become more stringent and consumer demand for low-odor products increases, BDMAEE is poised to play an increasingly important role in the epoxy resin industry. 🚀

References

[1] Sigma-Aldrich. (n.d.). Bis[2-(N,N-dimethylaminoethyl)] ether. Product Information.

[2] Air Products and Chemicals, Inc. (n.d.). DABCO® DME catalyst. Product Data Sheet.

[3] PubChem. (n.d.). Bis(2-(dimethylamino)ethyl) ether. National Center for Biotechnology Information.

[4] BASF. (n.d.). Lupragen® N 205. Product Information.

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