Bis[2-(N,N-Dimethylaminoethyl)] Ether (BDMAEE) for Low-Migration Food Packaging Materials Compliance: A Comprehensive Overview

Introduction

Bis[2-(N,N-Dimethylaminoethyl)] ether (BDMAEE), also known as DABCO® NE1060 (a registered trademark of Evonik Operations GmbH), is a tertiary amine catalyst widely employed in the production of polyurethane (PU) foams. Its primary role is to accelerate the reaction between isocyanates and polyols, leading to the formation of the urethane linkage. While BDMAEE offers significant benefits in PU foam manufacturing, its potential for migration from food packaging materials and subsequent consumer exposure raises concerns regarding food safety. This article provides a comprehensive overview of BDMAEE, focusing on its properties, applications in PU foam production, migration potential, regulatory compliance for food packaging materials, and strategies for minimizing its presence in food contact articles. We will explore various aspects, including product parameters, applications, safety considerations, and future trends, while adhering to rigorous and standardized language.

1. Product Overview

BDMAEE is a clear, colorless to slightly yellow liquid with a characteristic amine odor. It is soluble in water and most organic solvents. Its chemical structure features two dimethylaminoethyl groups linked by an ether linkage, providing two tertiary amine functionalities capable of catalyzing the urethane reaction.

1.1 Chemical Structure and Formula

• Chemical Name: Bis[2-(N,N-Dimethylaminoethyl)] ether
• Synonyms: 2,2′-Dimorpholinyldiethyl Ether; Dimethylaminoethyl Ether; DABCO® NE1060
• CAS Registry Number: 3033-62-3
• Molecular Formula: C₁₂H₂₆N₂O
• Molecular Weight: 214.35 g/mol
• Structural Formula: (CH₃)₂N-CH₂CH₂-O-CH₂CH₂-N(CH₃)₂

1.2 Physical and Chemical Properties

1.3 Product Specifications

The following table presents typical product specifications for commercially available BDMAEE:

2. Applications in Polyurethane Foam Production

BDMAEE is primarily used as a tertiary amine catalyst in the production of various types of PU foams, including flexible, rigid, and semi-rigid foams. Its efficacy in accelerating the urethane reaction makes it crucial for achieving desired foam properties and processing characteristics.

2.1 Catalytic Mechanism

BDMAEE acts as a nucleophilic catalyst, accelerating the reaction between isocyanates and polyols. The nitrogen atom in the tertiary amine group abstracts a proton from the hydroxyl group of the polyol, increasing its nucleophilicity and facilitating its attack on the electrophilic carbon atom of the isocyanate group. This process leads to the formation of the urethane linkage and the release of carbon dioxide, which acts as a blowing agent.

2.2 Types of PU Foams

• Flexible Foams: Used in mattresses, upholstery, and automotive seating. BDMAEE helps control the cell structure and density of flexible foams, contributing to their comfort and resilience.
• Rigid Foams: Used in insulation panels, refrigerators, and structural components. BDMAEE is crucial for achieving the desired closed-cell structure and thermal insulation properties of rigid foams.
• Semi-Rigid Foams: Used in automotive parts and packaging applications. BDMAEE provides a balance between flexibility and rigidity, making these foams suitable for impact absorption and cushioning.

2.3 Advantages of Using BDMAEE

• High Catalytic Activity: BDMAEE is a highly efficient catalyst, requiring relatively low concentrations to achieve desired reaction rates.
• Good Solubility: Its solubility in polyols and isocyanates ensures uniform distribution within the reaction mixture, leading to consistent foam properties.
• Controlled Reaction Rate: BDMAEE allows for precise control over the urethane reaction rate, enabling optimization of foam processing parameters.
• Improved Foam Properties: BDMAEE can contribute to improved foam properties, such as cell structure, density, and mechanical strength.

3. Migration Potential and Food Safety Concerns

While BDMAEE is essential for PU foam production, its potential to migrate from food packaging materials into food poses a risk to consumer health. The migration process is influenced by several factors, including the concentration of BDMAEE in the foam, the type of food being packaged, the temperature and duration of storage, and the barrier properties of the packaging material.

3.1 Factors Influencing Migration

• Concentration in the Foam: Higher concentrations of BDMAEE in the PU foam increase the driving force for migration.
• Type of Food: Fatty foods tend to absorb more BDMAEE than aqueous foods due to the lipophilic nature of the amine.
• Temperature and Duration: Elevated temperatures and prolonged storage periods accelerate the migration process.
• Packaging Material: The barrier properties of the packaging material play a crucial role in preventing or minimizing migration. Materials with low permeability to BDMAEE, such as aluminum foil or certain polymers with high density, can effectively reduce migration.
• Foam Structure: Open-cell foams generally exhibit higher migration rates compared to closed-cell foams due to the larger surface area exposed to the food.

3.2 Health Risks Associated with Exposure

Exposure to BDMAEE through food consumption can potentially lead to various health effects, including:

• Irritation: BDMAEE can cause irritation of the skin, eyes, and respiratory tract upon direct contact.
• Allergic Reactions: Some individuals may experience allergic reactions upon exposure to BDMAEE.
• Toxicological Concerns: Studies have raised concerns about the potential for BDMAEE to cause developmental or reproductive toxicity at high doses. Further research is needed to fully assess the long-term health effects of low-level exposure through food consumption.

3.3 Methods for Detecting Migration

Several analytical techniques are employed to detect and quantify the migration of BDMAEE from food packaging materials into food simulants. These methods typically involve extraction, separation, and detection steps.

• Gas Chromatography-Mass Spectrometry (GC-MS): This technique is widely used for identifying and quantifying volatile organic compounds, including BDMAEE, in food simulants.
• Liquid Chromatography-Mass Spectrometry (LC-MS): This technique is suitable for analyzing non-volatile or thermally labile compounds, and can be used to detect BDMAEE after derivatization.
• Headspace Gas Chromatography (HS-GC): This technique involves analyzing the volatile compounds present in the headspace above a sample, providing a sensitive method for detecting BDMAEE migration.

4. Regulatory Compliance for Food Packaging Materials

Due to the potential health risks associated with BDMAEE migration, regulatory bodies worldwide have established guidelines and regulations governing its use in food packaging materials. These regulations aim to minimize consumer exposure to BDMAEE and ensure food safety.

4.1 European Union (EU)

• Regulation (EC) No 1935/2004: This framework regulation establishes the general principles for all food contact materials, requiring them to be safe, inert, and not to transfer their constituents to food in quantities that could endanger human health or bring about an unacceptable change in the composition of the food.
• Regulation (EU) No 10/2011: This regulation specifically addresses plastic materials and articles intended to come into contact with food. It establishes specific migration limits (SMLs) for certain substances, including amines, but does not have a specific SML for BDMAEE. However, it does include an overall migration limit (OML) of 10 mg/dm² for plastic materials. Manufacturers must ensure that the total migration of all substances from the plastic material does not exceed this limit.
• EFSA Opinions: The European Food Safety Authority (EFSA) provides scientific opinions on the safety of substances used in food contact materials. EFSA has evaluated the safety of BDMAEE and may provide guidance on acceptable exposure levels.

4.2 United States (US)

• Food and Drug Administration (FDA): The FDA regulates food contact substances in the US. Substances used in food packaging must be either generally recognized as safe (GRAS) or approved through a food contact notification (FCN) process. While BDMAEE is not specifically listed in FDA regulations for direct food contact, it may be used in indirect food contact applications if it meets certain criteria and does not result in significant migration into food.
• 21 CFR Part 175: This section of the Code of Federal Regulations addresses indirect food additives, including components of paper and paperboard in contact with food.
• 21 CFR Part 177: This section addresses indirect food additives, including polymers.

4.3 China

• GB Standards: China has a series of national standards (GB standards) that regulate food contact materials and articles. These standards specify requirements for materials, testing methods, and migration limits. Relevant GB standards include:
  • GB 4806.1-2016: General safety requirements for food contact materials and articles.
  • GB 9685-2016: Hygienic standards for uses of additives in food containers and packaging materials.
  • GB 31604.1-2015: General principles for the migration test of food contact materials and articles.

4.4 Other Regions

Many other countries and regions have their own regulations and guidelines for food contact materials, often based on the principles established by the EU and the US. Manufacturers must comply with the specific regulations of the countries where their products are sold.

5. Strategies for Minimizing BDMAEE Migration

Several strategies can be implemented to minimize the migration of BDMAEE from PU foams used in food packaging applications. These strategies focus on reducing the concentration of BDMAEE in the foam, improving the foam’s structure, and enhancing the barrier properties of the packaging material.

5.1 Reducing BDMAEE Concentration

• Optimize Catalyst Dosage: Carefully optimize the dosage of BDMAEE to ensure that only the minimum amount required for achieving desired foam properties is used.
• Use Alternative Catalysts: Explore the use of alternative catalysts that are less prone to migration or have lower toxicity profiles. Examples include reactive amine catalysts that become chemically bound to the polymer matrix during the foaming process, or metal catalysts.
• Post-Curing: Implement a post-curing process to further react any residual isocyanates and polyols, reducing the potential for BDMAEE release. Post-curing involves exposing the foam to elevated temperatures for a specified period, promoting further crosslinking and reducing the concentration of unreacted components.

5.2 Improving Foam Structure

• Closed-Cell Foam: Utilize closed-cell foam structures whenever possible, as they offer a lower surface area for migration compared to open-cell foams.
• Optimize Cell Size: Optimize the cell size and uniformity of the foam to minimize the surface area exposed to the food.
• Surface Treatment: Apply surface treatments to the foam to seal the surface and reduce migration.

5.3 Enhancing Barrier Properties

• Lamination: Laminate the PU foam with a barrier layer, such as aluminum foil, polyethylene (PE), or polypropylene (PP), to prevent migration.
• Coatings: Apply barrier coatings to the surface of the foam to reduce its permeability to BDMAEE.
• Modified Atmosphere Packaging (MAP): Employ modified atmosphere packaging techniques to reduce the rate of degradation and migration.

5.4 Selection of Raw Materials

• High-Purity Raw Materials: Use high-purity polyols and isocyanates to minimize the presence of impurities that could contribute to migration.
• Low-Migration Additives: Select additives, such as surfactants and stabilizers, that have low migration potential.

6. Future Trends and Research Directions

The field of food packaging materials is constantly evolving, with a focus on developing safer and more sustainable solutions. Future trends and research directions related to BDMAEE and other amine catalysts include:

• Development of Reactive Amine Catalysts: Research is ongoing to develop reactive amine catalysts that become chemically bound to the polymer matrix during the foaming process, eliminating the potential for migration.
• Bio-Based Catalysts: Exploration of bio-based catalysts derived from renewable resources as alternatives to traditional amine catalysts.
• Advanced Analytical Techniques: Development of more sensitive and accurate analytical techniques for detecting and quantifying trace levels of amine migration in food simulants.
• Risk Assessment and Modeling: Refinement of risk assessment models to better predict the migration behavior of amine catalysts and assess the potential health risks associated with exposure.
• Sustainable Packaging Materials: Development of sustainable packaging materials that are biodegradable or compostable, reducing the environmental impact of food packaging waste.

7. Conclusion

BDMAEE is a valuable catalyst in the production of PU foams used in various applications, including food packaging. However, its potential for migration and associated health risks necessitate careful consideration and implementation of strategies to minimize exposure. Regulatory compliance is paramount, and manufacturers must adhere to the specific regulations of the countries where their products are sold. By optimizing catalyst dosage, improving foam structure, enhancing barrier properties, and exploring alternative catalysts, it is possible to significantly reduce the migration of BDMAEE and ensure the safety of food packaging materials. Continued research and development efforts are crucial for advancing the field of food packaging materials and creating safer and more sustainable solutions for the future. The ongoing development of reactive and bio-based catalysts, along with advanced analytical techniques and refined risk assessment models, will contribute to minimizing the risks associated with amine migration and ensuring the safety of food products for consumers.

Literature Sources

• EFSA (European Food Safety Authority). Scientific Opinion on the safety assessment of substances used in plastic food contact materials. EFSA Journal, various years. (Note: Specify the relevant EFSA opinions based on specific substances and years)
• FDA (U.S. Food and Drug Administration). Code of Federal Regulations, Title 21, Parts 175 and 177.
• GB Standards. National Standards of the People’s Republic of China for Food Contact Materials and Articles. (Note: Specify the relevant GB standards based on material type and application)
• Kirwan, M. J., & Strawbridge, J. W. (2003). Plastics packaging and food safety. Pira International.
• Robertson, G. L. (2016). Food Packaging: Principles and Practice. CRC press.
• Wypych, G. (2017). Handbook of Polymers. ChemTec Publishing.
• Dominguez, A. R., et al. (2019). Migration of amine catalysts from polyurethane foams into food simulants. Food Chemistry, 283, 450-457. (Note: This is a placeholder, replace with actual relevant research papers).
• Smith, J. P., et al. (2020). Evaluation of alternative catalysts for polyurethane foam production with reduced migration potential. Journal of Applied Polymer Science, 137(10), 48501. (Note: This is a placeholder, replace with actual relevant research papers).

This article provides a detailed overview of BDMAEE, its applications, safety concerns, and strategies for minimizing migration. Remember to replace the placeholder literature sources with actual relevant research papers.

Extended reading:https://www.newtopchem.com/archives/category/products/page/169

Extended reading:https://www.bdmaee.net/jeffcat-dmdee-catalyst-cas11225-78-5-huntsman/

Extended reading:https://www.bdmaee.net/tegoamin-bde-catalyst-cas121-54-0-degussa-ag/

Extended reading:https://www.newtopchem.com/archives/94

Extended reading:https://www.newtopchem.com/archives/43950

Extended reading:https://www.bdmaee.net/dabco-ne1060-catalyst-cas10046-12-1-evonik-germany/

Extended reading:https://www.newtopchem.com/archives/1808

Extended reading:https://www.bdmaee.net/wp-content/uploads/2022/08/-NE500-non-emission-amine-catalyst-NE500-strong-gel-amine-catalyst-NE500.pdf

Extended reading:https://www.newtopchem.com/archives/672

Extended reading:https://www.newtopchem.com/archives/42767