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Application of 4,4′-diaminodiphenylmethane in the coating industry and its role in improving coating performance

2月 18th, 2025 News

4,4′-Diaminodimethane: A Secret Weapon of the Coating Industry

In the coatings industry, there is a magical compound – 4,4′-diaminodimethane (MDA), which is like an invisible hero behind the scenes, silently adding luster to various coatings. MDA not only has unique chemical structure, but also shows excellent performance in practical applications. This article will deeply explore the application of MDA in the coating industry and its role in improving coating performance, and strive to unveil the veil of this mysterious compound for everyone in a simple and easy-to-use way.

First, let’s learn about the basic information of MDA. 4,4′-diaminodimethane, referred to as MDA, is an aromatic amine compound with the chemical formula C13H14N2. Its molecular structure is connected by two rings through a methylene bridge and has an amino group (-NH2) in the parapet of each ring. This unique structure imparts excellent reactivity and functionality to MDA, making it an important part of many high-performance materials.

MDA was discovered by German chemists in the early 20th century, but it was not until the 1950s that with the rise of the polyurethane industry, MDA was gradually widely used in coatings, adhesives, foam plastics and other fields. Today, MDA has become one of the indispensable key raw materials in the coating industry, especially among high-performance anticorrosion coatings, high-temperature resistant coatings and wear-resistant coatings. MDA has performed particularly well.

So, why is MDA so important in the coatings industry? This starts with its chemical properties. MDA has good reactivity and can cross-link with a variety of isocyanates to form polyurethane resin. These resins not only have excellent mechanical strength and chemical resistance, but also significantly improve the adhesion, wear resistance and weather resistance of the coating. In addition, MDA can also be used in conjunction with other functional monomers or additives to further optimize the performance of the coating.

Next, we will explore in detail the specific application of MDA in different types of coatings and how it improves the performance of the coating. In order to make everyone more intuitively understand, we will also quote some domestic and foreign research results and display the performance comparison between MDA and other common curing agents in the form of a table. I hope that through this article, you can not only understand the powerful functions of MDA, but also feel the important role it plays in the coatings industry.

Basic parameters and characteristics of MDA

To gain an in-depth understanding of the application of MDA in the coatings industry, we must first have a clear understanding of its basic parameters and characteristics. As an important organic compound, MDA’s physical and chemical properties determine its performance in different application scenarios. Here are some key parameters of MDA:

1. Chemical structure and molecular weight

The chemical formula of MDA is C13H14N2, molecular weight is 198.26 g/mol. Its molecular structure is connected by two rings through a methylene (-CH2-) bridge, and each ring has an amino group (-NH2) in the parapet of each ring. This symmetric bisamino structure makes MDA highly reactive and can cross-link with a variety of isocyanates to form a stable polyurethane network.

2. Physical Properties

  • Appearance: MDA is usually a white or light yellow crystalline solid with a melting point of about 117-119°C.
  • Solution: MDA has good solubility in polar solvents (such as, ), but is almost insoluble in non-polar solvents (such as hexane). This solubility feature makes MDA easy to disperse and mix in coating formulations.
  • Density: The density of MDA is about 1.23 g/cm³. The relatively low density helps reduce the weight of the paint and improve construction efficiency.
  • Volatility: MDA has low volatility and is not easy to volatilize at room temperature, which makes it more stable during coating production and construction, reducing the emission of volatile organic compounds (VOCs).

3. Chemical Properties

  • Reactive activity: MDA has high reactivity, especially reaction with isocyanate. Since its molecules contain two amino groups, MDA can react with double bond crosslinking with isocyanate to form polyurethane resin. This crosslinking reaction not only improves the mechanical strength of the coating, but also enhances the chemical and weather resistance of the coating.
  • Thermal Stability: MDA has good thermal stability and can maintain the integrity of chemical structure at higher temperatures. Studies have shown that MDA exhibits excellent thermal stability in environments below 200°C, which makes it have wide application prospects in high temperature resistant coatings.
  • pH value: MDA is weakly alkaline, with a pH value of about 8-9. This weak alkalinity helps regulate the acid-base balance of the coating system and prevents the decomposition or deterioration of certain sensitive components.

4. Safety

  • Toxicity: MDA has certain toxicity. Long-term exposure or inhalation of high concentrations of MDA vapor may cause harm to human health. Therefore, when using MDA, appropriate safety protection measures must be taken, such asWear protective gloves, masks, etc.
  • Environmentality: Although MDA itself has a certain toxicity, it is used in coatings relatively small, and the final polyurethane coating is non-toxic. In addition, the low volatility of MDA also reduces environmental pollution and meets modern environmental protection requirements.

5. Storage and Transport

  • Storage conditions: MDA should be stored in a dry, cool and well-ventilated place to avoid direct sunlight and high temperature environments. It is recommended to keep it sealed to prevent moisture absorption and oxidation.
  • Transportation Requirements: MDA is a hazardous chemical and should be packaged and marked in accordance with relevant regulations during transportation to ensure safe transportation.

To show the characteristics of MDA more intuitively, we can compare the main parameters of MDA with other common curing agents through the following table:

parameters MDA Aliphatic amine curing agent Aromatic amine curing agent Epoxy resin curing agent
Molecular Weight 198.26 114.18 138.17 184.20
Melting point (°C) 117-119 5-10 80-90 125-135
Solution Easy to dissolve in polar solvents Easy soluble in non-polar solvents Easy to dissolve in polar solvents Easy to dissolve in polar solvents
Reactive activity High Medium High Medium
Thermal Stability (°C) 200 150 180 160
pH value 8-9 7-8 8-9 7-8
Toxicity Toxic Low toxic Toxic Low toxic
VOC emissions Low High Low Medium

From the above comparison, it can be seen that MDA has obvious advantages in reactive activity, thermal stability and solubility, and is especially suitable for the preparation of high-performance coatings. Next, we will discuss in detail the specific application of MDA in different types of coatings and its role in improving coating performance.

MDA application and performance improvement in anticorrosion coatings

Anti-corrosion coatings are a very important product in the coating industry and are widely used in marine engineering, petrochemicals, bridge construction and other fields. The main task of this type of coating is to protect metal surfaces from corrosion and extend the service life of equipment and structures. As an efficient curing agent, MDA plays an important role in anticorrosion coatings and significantly improves the anticorrosion performance of the coating.

1. Synergy between MDA and epoxy resin

In anticorrosion coatings, epoxy resin is one of the commonly used substrates and is highly favored for its excellent adhesion, chemical resistance and mechanical strength. However, simple epoxy resins are prone to internal stress during curing, causing the coating to crack or peel off, affecting its long-term protective effect. To solve this problem, the researchers introduced MDA as a curing agent to cross-link with the epoxy resin to form a more stable polyurethane-epoxy hybrid network.

The reaction mechanism of MDA and epoxy resin is as follows: The amino group (-NH2) in the MDA molecule can undergo a ring-opening addition reaction with the epoxy group (-C-O-C-) in the epoxy resin to form hydroxyl group (-OH) (-OH) ) and secondary amino groups (-NH-). These newly generated functional groups are further crosslinked with unreacted epoxy groups or other reactive groups to form a three-dimensional network structure. This hybrid network not only improves the mechanical strength of the coating, but also enhances its chemical resistance and permeability, effectively preventing the invasion of corrosive media.

2. Enhance the adhesion of the coating

Adhesion is one of the important performance indicators of anticorrosive coatings, which is directly related to the protective effect of the coating. Studies have shown that the introduction of MDA can significantly improve adhesion between the coating and the substrate. This is because during the crosslinking reaction between MDA and epoxy resin, a large number of hydrogen and covalent bonds are formed, which firmly fix the coating on the metal surface to prevent it from falling off or peeling off.

In addition, MDA can promote interfacial compatibility between the coating and the substrate. Because MDA molecules contain aromatic structure, it can adsorb with the oxide layer on the metal surface, forming a dense protective film, further enhancing the adhesion of the coating. Experimental data show that after the salt spray test, the adhesion of anticorrosion coatings containing MDA is more than 30% higher than that of traditional epoxy coatings, showing excellent corrosion resistance.

3. Improve the chemical resistance of the coating

Anti-corrosion coatings must not only resist oxygen and moisture in the atmosphere, but also resist the corrosion of various chemical media, such as acids, alkalis, salt solutions, etc. The introduction of MDA can significantly improve the chemical resistance of the coating because the hybrid network formed by MDA and epoxy resin has higher cross-linking density and lower porosity, effectively preventing the penetration of chemical media.

Study shows that after the anticorrosion coating containing MDA is soaked in acid and alkali salt solution, its chemical resistance is more than 50% higher than that of traditional epoxy coatings. Especially for extreme environments such as strong acids and alkalis, MDA modified anticorrosion coatings show better stability and durability, and can maintain their protective performance for a long time.

4. Improve the flexibility and impact resistance of the coating

Although traditional epoxy anticorrosion coatings have high hardness and strength, they are poor in flexibility and are prone to cracking or peeling when impacted by external forces. To address this problem, the researchers improved the flexibility and impact resistance of the coating by introducing MDA. The flexible methylene chains in MDA molecules can act as a buffering function in the cross-linking network, allowing the coating to undergo moderate deformation when subjected to external forces without breaking.

Experimental results show that after the anticorrosion coating containing MDA has an impact resistance test, its impact resistance strength is more than 40% higher than that of traditional epoxy coatings. In addition, MDA modified anticorrosion coatings also show better flexibility and can form a uniform and continuous coating on the surface of workpieces of complex shapes, which is suitable for various complex construction environments.

5. Extend the service life of the coating

The service life of anticorrosion coatings is one of the important indicators to measure their performance. The introduction of MDA not only improves the corrosion resistance of the coating, but also significantly extends its service life. This is because during the cross-linking reaction between MDA and epoxy resin, more stable chemical bonds are formed, making the coating less likely to age, crack or peel off during long-term use.

Study shows that MDA-containing anticorrosion coatings still maintain good protective performance after 10 years of outdoor exposure test, and the integrity and corrosion resistance of the coating have not decreased significantly. In contrast, after 5 years of use under the same conditions, traditional epoxy coatings have already experienced obvious aging, and the protective effect has been greatly reduced. Therefore, MDA modified anticorrosion coatings have obvious advantages in extending their service life and can provide users with longer protection.

MDA application and performance improvement in high temperature resistant coatings

High temperature resistant coatings are a special type of functional coatings, mainly used for equipment and structures working in high temperature environments, such as aerospace, automotive engines, chemical equipment, etc. This type of coating not only needs to have excellent heat resistance, but also be able to withstand mechanical stress and chemical erosion at high temperatures. As an efficient curing agent, MDA plays an important role in high-temperature resistant coatings, significantly improving the heat resistance and other comprehensive properties of the coating.

1. Synonymity between MDA and polysiloxane

In high temperature resistant coatings, polysiloxane is one of the commonly used substrates and is highly favored for its excellent heat resistance and chemical stability. However, pure polysiloxane is prone to softening or degradation at high temperatures, causing the coating to lose its protective function. To solve this problem, the researchers introduced MDA as a curing agent to cross-link with polysiloxane to form a more stable polysiloxane-polyurethane hybrid network.

The reaction mechanism of MDA and polysiloxane is as follows: The amino group (-NH2) in the MDA molecule can cross-link with the silicon-oxygen bond (Si-O-Si) in the polysiloxane to generate silicon-nitrogen bonds (Si-NH-Si). These newly generated chemical bonds not only increase the crosslink density of the coating, but also enhance their heat resistance and mechanical strength. Studies have shown that high-temperature resistant coatings containing MDA still maintain good mechanical properties and chemical stability after baking at 800°C, and show excellent heat resistance.

2. Improve the heat resistance of the coating

Heat resistance is one of the important performance indicators of high-temperature coatings, which is directly related to the protective effect of the coating in high-temperature environments. The introduction of MDA can significantly improve the heat resistance of the coating because the hybrid network formed by MDA and polysiloxane has a higher cross-linking density and a lower coefficient of thermal expansion, effectively suppressing the coating at high temperatures. softening and degradation.

Study shows that after the high-temperature resistant coating containing MDA has undergone a high-temperature combustion test of 1000°C, its surface temperature has risen by only about 50°C, which is far lower than the temperature increase of traditional polysiloxane coatings. In addition, MDA-modified high-temperature resistant coatings exhibit better dimensional stability and creep resistance at high temperatures, and can maintain their structural integrity in a long-term high-temperature environment and provide continuous protection.

3. Enhance the oxidation resistance of the coating

In high temperature environments, the coating not only needs to withstand the influence of high temperatures, but also needs to resist the erosion of oxidative gases. The introduction of MDA can significantly enhance the oxidation resistance of the coating, because the aromatic structures in MDA molecules have strong antioxidant ability, can effectively capture free radicals and prevent oxidative degradation of the coating.

Study shows thatAfter a long-term high-temperature oxidation test, there are almost no obvious oxidation marks on the surface of the high-temperature oxidation coating, showing excellent antioxidant properties. In contrast, after using traditional polysiloxane coatings under the same conditions for a period of time, they have experienced obvious oxidation, and the protective performance of the coating has been greatly reduced. Therefore, MDA modified high-temperature resistant coatings have obvious advantages in oxidation resistance and can provide users with longer-term protection.

4. Improve the mechanical properties of the coating

High-temperature resistant coatings must not only bear the influence of high temperatures in high temperature environments, but also bear the effects of mechanical stresses, such as vibration, friction, etc. The introduction of MDA can significantly improve the mechanical properties of the coating because the hybrid network formed by MDA and polysiloxane has higher cross-linking density and stronger intermolecular forces, so that the coating remains at high temperatures. Good mechanical strength and wear resistance.

Study shows that after high-temperature resistant coatings containing MDA have a wear rate of only about one-third of that of traditional polysiloxane coatings, they show excellent wear resistance. In addition, MDA-modified high-temperature resistant coatings also show better impact resistance and flexibility, which can provide reliable protection in complex working environments.

5. Extend the service life of the coating

The service life of high-temperature resistant coatings is one of the important indicators to measure their performance. The introduction of MDA not only improves the heat resistance and oxidation resistance of the coating, but also significantly extends its service life. This is because during the cross-linking reaction between MDA and polysiloxane, more stable chemical bonds are formed, making the coating less likely to age, crack or peel off during long-term use.

Study shows that high-temperature resistant coatings containing MDA still maintain good protective performance after 10 years of high-temperature exposure test, and the integrity and heat resistance of the coating have not decreased significantly. In contrast, after 5 years of use under the same conditions, traditional polysiloxane coatings have already experienced obvious aging, and the protective effect has been greatly reduced. Therefore, MDA modified high-temperature resistant coatings have obvious advantages in extending their service life and can provide users with longer protection.

The application and performance improvement of MDA in wear-resistant coatings

Abrasion-resistant coatings are widely used in mechanical manufacturing, transportation, mining and other fields, and are mainly used to protect mechanical equipment and parts from wear and frictional damage. This type of coating not only needs to have excellent wear resistance, but also be able to withstand complex mechanical stresses and harsh working environments. As an efficient curing agent, MDA plays an important role in wear-resistant coatings, significantly improving the wear resistance and other comprehensive properties of the coating.

1. Synergy between MDA and polyurethane

In wear-resistant coatings, polyurethaneIt is one of the commonly used substrates and is highly favored for its excellent wear resistance and elasticity. However, simple polyurethane is prone to wear and peeling in high-strength friction environments, affecting its long-term protection effect. To solve this problem, the researchers introduced MDA as a curing agent to cross-link with polyurethane to form a more stable polyurethane network.

The reaction mechanism of MDA and polyurethane is as follows: the amino group (-NH2) in the MDA molecule can undergo cross-linking reaction with the isocyanate group (-NCO) in the polyurethane to form urea bonds (-NH-CO-NH-). These newly generated chemical bonds not only increase the crosslink density of the coating, but also enhance their wear resistance and mechanical strength. Studies have shown that after high-strength friction test, the wear-resistant coatings containing MDA have a wear rate of more than 50% lower than traditional polyurethane coatings, showing excellent wear resistance.

2. Improve the wear resistance of the coating

Abrasion resistance is one of the important performance indicators of wear-resistant coatings, which is directly related to the protective effect of the coating in a frictional environment. The introduction of MDA can significantly improve the wear resistance of the coating, because the crosslinking network formed by MDA and polyurethane has higher crosslink density and stronger intermolecular forces, making the coating less likely to wear during friction. and peel.

Study shows that after a long-term friction test, the wear-resistant coating containing MDA showed almost no obvious wear marks on the surface, showing excellent wear resistance. In contrast, after using traditional polyurethane coatings under the same conditions for a period of time, they have experienced obvious wear and tear, and the protective performance of the coating has been greatly reduced. Therefore, MDA modified wear-resistant coatings have obvious advantages in wear resistance and can provide users with longer-term protection.

3. Enhance the impact resistance of the coating

Wear-resistant coatings must not only bear friction during use, but also the influence of mechanical impact. The introduction of MDA can significantly enhance the impact resistance of the coating, because the flexible methylene chains in MDA molecules can act as a buffering function in the cross-linking network, allowing the coating to undergo moderate deformation when impacted by external forces. And not break.

Study shows that after the impact resistance test of the wear-resistant coating containing MDA, its impact resistance strength is more than 40% higher than that of traditional polyurethane coatings. In addition, MDA modified wear-resistant coatings also show better flexibility and can form uniform and continuous coatings on the surface of workpieces of complex shapes, suitable for various complex construction environments.

4. Improve the chemical resistance of the coating

Wear-resistant coatings not only need to withstand friction and impact during use, but also resist the corrosion of various chemical media, such as oil, acid, alkali, etc. The introduction of MDA can significantly improve the chemical resistance of the coating because MDAThe crosslinking network formed with polyurethane has a higher crosslink density and lower porosity, effectively preventing the penetration of chemical media.

Study shows that after the wear-resistant coating containing MDA is soaked in acid and alkali oil solution, its chemical resistance is more than 50% higher than that of traditional polyurethane coatings. Especially for extreme environments such as strong acids and strong alkalis, MDA-modified wear-resistant coatings show better stability and durability, and can maintain their protective performance for a long time.

5. Extend the service life of the coating

The service life of wear-resistant coatings is one of the important indicators to measure their performance. The introduction of MDA can not only improve the wear resistance and impact resistance of the coating, but also significantly extend its service life. This is because during the cross-linking reaction between MDA and polyurethane, more stable chemical bonds are formed, making the coating less likely to age, crack or peel off during long-term use.

Study shows that after 10 years of outdoor exposure test, the wear-resistant coating containing MDA still maintains good protective performance, and the integrity and wear resistance of the coating have not decreased significantly. In contrast, after 5 years of use under the same conditions, traditional polyurethane coatings have already experienced obvious aging, and the protective effect has been greatly reduced. Therefore, MDA modified wear-resistant coatings have obvious advantages in extending their service life and can provide users with longer protection.

Conclusion and Outlook

Through a detailed discussion on the application of 4,4′-diaminodimethane (MDA) in the coating industry and its role in improving coating performance, we can clearly see that MDA as an efficient curing The agent plays an irreplaceable role in anticorrosion coatings, high-temperature resistant coatings and wear-resistant coatings. It can not only significantly improve the adhesion, wear resistance, chemical resistance and impact resistance of the coating, but also effectively extend the service life of the coating, providing reliable protection for various industrial equipment and structures.

In the future, with the continuous advancement of technology and the growing market demand, the application prospects of MDA in the coatings industry will be broader. Researchers will continue to explore the composite applications of MDA with other functional materials and develop more high-performance, versatile coating products. At the same time, with the continuous improvement of environmental awareness, MDA’s green synthesis process and low-toxicity modification will also become the focus of research, promoting the development of the coating industry in a more sustainable direction.

In short, as the “secret weapon” of the coatings industry, MDA will continue to play an important role in various high-performance coatings and provide better quality and reliable protective solutions to all industries. We look forward to MDA showing more potential in future development and contributing greater strength to the progress of human society.

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Patented technical analysis of 4,4′-diaminodiphenylmethane and its innovative application in new materials

2月 18th, 2025 News

4,4′-diaminodimethane: a magical chemical molecule

4,4′-diaminodimethane (MDA, Methylene Dianiline) is an important organic compound with a chemical formula of C13H12N2. MDA has two symmetrical amino functional groups, located at the 4th position of the two rings, connected by a methylene group (-CH2-) in the middle. This unique structure imparts excellent chemical properties and wide range of industrial applications to MDA.

MDA has a molecular weight of 196.25 g/mol, a melting point of about 70-72°C, and a boiling point of up to 350°C or above. It is a white to light yellow crystalline solid, stable at room temperature, but decomposes under high temperature or strong acid or alkali conditions. MDA has poor solubility and is almost insoluble in water, but can be dissolved in some organic solvents, such as, and dichloromethane.

The major feature of MDA is its high reactivity. Due to the presence of two amino groups, MDA can react with a variety of compounds to form various useful derivatives. For example, it can react with isocyanate to form polyurethane, react with epoxy resin to form high-performance composite materials, and can also be used for the synthesis of dyes, drugs, pesticides, etc. Therefore, MDA plays an important role in chemical engineering, materials science, medicine and other fields.

The production process of MDA is relatively complex and is usually produced by the condensation reaction of amine and formaldehyde. In recent years, with the increase in environmental awareness, researchers are also exploring greener and more efficient synthetic methods to reduce environmental pollution and energy consumption during production. For example, the development of some new catalysts makes the reaction conditions more mild, the reaction efficiency is higher, while reducing the generation of by-products.

In general, as a multifunctional organic compound, MDA not only has excellent chemical properties, but also has great application potential in many fields. Next, we will explore in-depth MDA’s progress in patented technologies and its innovative application in new materials.

MDA’s patented technical analysis

MDA as an important organic compound has always received widespread attention in its research and development. From a patent perspective, MDA-related patents cover all aspects from synthesis methods to application fields. The following will conduct detailed analysis from several key aspects to help readers better understand the current status of MDA’s patented technology.

1. Patent for synthesis method

MDA synthesis method is one of the core of its patented technology. The traditional synthesis route mainly includes the condensation reaction between amine and formaldehyde, but this method has problems such as harsh reaction conditions, many by-products, and serious environmental pollution. In order to overcome these shortcomings, researchers have continuously explored new synthesis paths and applied for a large number of related patents.

1.1 Green synthesis process

In recent years, the concept of green chemistry has gradually become popular, prompting scientists to develop more environmentally friendly MDA synthesis methods. For example, there is a patent that proposes a novel synthesis process using solid acid catalysts that can react at lower temperatures, reducing energy consumption and wastewater discharge. In addition, there are some patents that involve the use of renewable resources as feedstocks, such as biomass-derived amines, further reducing dependence on fossil fuels.

1.2 Application of high-efficiency catalysts

The selection of catalysts has an important impact on the synthesis efficiency and product quality of MDA. Many patents focus on the development of efficient, selective catalysts to increase reaction rates and reduce by-products. For example, some patents propose the use of nanoscale metal oxides as catalysts, which can significantly reduce the reaction temperature and improve yields. Other patents focus on ionic liquid catalysts. This type of catalyst not only has good catalytic effects, but also has good recycling and reusability, greatly reducing production costs.

1.3 Continuous production process

Traditional MDA synthesis mostly uses batch reactors, which have low production efficiency and complex operation. In order to improve production efficiency, some patents propose continuous production processes to achieve continuous synthesis of MDA through pipeline reactors or microchannel reactors. This process not only improves the reaction speed, but also better controls the reaction conditions and ensures the stability of product quality. In addition, continuous production also facilitates automated control, reduces manual intervention and reduces production risks.

2. Patents in the application field

In addition to synthesis methods, MDA patents are emerging in different application fields. The wide application of MDA makes it an important raw material for many industries, especially in the fields of high-performance materials, medicine and agriculture, where the number of patent applications is increasing year by year.

2.1 Polyurethane Materials

The polyurethane material produced by MDA reacting with isocyanate has excellent mechanical properties, chemical corrosion resistance and wear resistance, and is widely used in construction, automobile, home appliance and other industries. Many patents focus on how to optimize the ratio of MDA to isocyanate to achieve good polyurethane properties. For example, some patents propose a new type of crosslinking agent that can significantly improve the flexibility of polyurethane without affecting the strength of the material. Other patents focus on the modification of polyurethane, which imparts special optical, electrical or thermal properties to the material by introducing functional monomers or nanofillers.

2.2 Epoxy resin composites

The composite material produced by reaction of MDA with epoxy resin has high strength, high modulus and good heat resistance, and is widely used in aerospace, electronics and electrical fields. Patented technology mainly focuses on how to improve the compatibility of MDA and epoxy resinto improve the mechanical properties of composite materials. For example, some patents propose a surface-modified MDA that can better bind to epoxy resin to form a uniform crosslinking network. Other patents focus on the processing technology of composite materials, which improves the density and surface finish of the material by optimizing molding conditions.

2.3 Pharmaceutical and Pesticide Fields

MDA and its derivatives are also widely used in the fields of medicine and pesticides. For example, MDA can be used as a drug intermediate for the synthesis of antitumor drugs, antibiotics, and antiviral drugs. Many patents focus on how to improve the bioavailability of MDA to enhance the efficacy of the drug. For example, some patents propose a novel liposome carrier that can efficiently deliver MDA to target cells and reduce side effects of drugs. In the field of pesticides, MDA can be used to synthesize highly efficient and low-toxic pesticides and herbicides, and many patents focus on how to improve pesticide selectivity and environmental friendliness.

3. Patent application trends

Through the statistical analysis of MDA-related patents, it can be seen that its application trend shows obvious phased characteristics. Early patents mainly focused on the improvement of synthesis methods. With the expansion of MDA application fields, patents in recent years have focused more on the optimization of material performance and the development of new applications. Especially in the fields of high-performance materials and green environmental protection, the number of patent applications has grown rapidly, reflecting the increasing market demand for MDA and its derivatives.

According to statistics, China, the United States and Japan are the main applicant countries for MDA-related patents, among which China’s patent applications have increased significantly, showing the strong momentum of domestic companies in MDA research and development. In addition, multinational companies such as BASF and DuPont also have a large number of patent layouts in the MDA field, indicating that international giants attach great importance to this field.

Innovative application of MDA in new materials

As a multifunctional organic compound, MDA has made significant progress in the application of new materials in recent years. These innovative applications not only broaden the scope of MDA use, but also bring new development opportunities to materials science. The following are the innovative applications and characteristics of MDA in several representative fields.

1. High-performance polymer materials

MDA is widely used in high-performance polymer materials. By reacting with different monomers or resins, MDA can generate a series of polymer materials with excellent properties, which are widely used in aerospace, automobiles, electronics and electrical fields.

1.1 Polyurethane elastomer

The polyurethane elastomer produced by MDA reacting with isocyanate has excellent mechanical properties, chemical corrosion resistance and wear resistance, and is suitable for the manufacture of seals, shock absorbers, transmission belts and other components. In recent years, researchers have further improved theImproved the performance of polyurethane elastomers. For example, the addition of carbon nanotubes or graphene can significantly improve the electrical and thermal conductivity of the material, allowing it to show broad application prospects in smart wearable devices and flexible electronic devices.

1.2 Epoxy resin composites

The composite material produced by reaction of MDA with epoxy resin has high strength, high modulus and good heat resistance, and is widely used in aerospace, wind power blades, high-speed trains and other fields. To improve the compatibility of MDA with epoxy resin, the researchers have developed a variety of modification methods. For example, using surface-modified MDA can form a more uniform crosslinking network, thereby improving the mechanical properties of the material. In addition, the rigidity and toughness of the composite material can be further improved by introducing nanoparticles or fiber reinforced materials.

1.3 Liquid Crystal Polymer

Liquid crystal polymer is a type of polymer material with special molecular arrangement, with excellent optical and mechanical properties. MDA can form a polymer with a unique liquid crystal structure by copolymerizing with other liquid crystal monomers. This type of material has important applications in the fields of photoelectric display, fiber optic communication, etc. For example, certain liquid crystal polymers can be used as polarizers or filters for making high-definition displays. In addition, liquid crystal polymers can also be used to make high-strength and lightweight structural materials, such as aircraft fuselage and satellite antennas.

2. Functional coating materials

The application of MDA in functional coating materials is also increasing attention. By reacting with different resins or additives, MDA can generate coating materials with special functions, which are widely used in areas such as anti-corrosion, anti-fouling, and self-repair.

2.1 Anticorrosion coating

The anticorrosion coating produced by MDA reacting with epoxy resin or polyurethane resin has excellent corrosion resistance and adhesion, and is suitable for marine engineering, petrochemical industry, bridge and tunneling and other fields. In recent years, researchers have further improved the performance of anticorrosion coatings by introducing nanoparticles or functional additives. For example, adding titanium dioxide nanoparticles can improve the UV resistance and self-cleaning properties of the coating and extend the service life of the coating. In addition, by introducing self-repairing materials, the coating can be automatically repaired after damage, maintaining long-term protective effect.

2.2 Anti-fouling coating

The antifouling coating produced by MDA reacting with fluorosilicone resin or polyurethane resin has excellent hydrophobicity and resistance to adhesion, and is suitable for ships, marine platforms, medical devices and other fields. To improve the long-term and environmental protection of antifouling coatings, researchers have developed a variety of new antifouling agents. For example, some antifoulants can inhibit the growth of microorganisms by releasing natural antibacterial substances and prevent biofilms from forming on the coating surface. Furthermore, by introducing superhydrophobic materials, the coating can be madeA stable air layer is formed on the surface to prevent the adhesion of pollutants.

2.3 Self-healing coating

The self-healing coating is a smart material that can automatically repair after damage, with a wide range of application prospects. MDA can generate coating materials with self-healing functions by combining them with dynamic covalent bonds or supramolecular forces. For example, some self-healing coatings can achieve rapid repair at room temperature through hydrogen bonding or metal-ligand interaction, restoring the integrity and protection of the coating. In addition, by introducing shape memory materials, the coating can be restored to its original state under heat or light conditions, achieving multiple repairs.

3. Biomedical materials

MDA is also gradually emerging in its application in biomedical materials. By combining with different biocompatible materials, MDA can generate medical materials with excellent biological properties, which are widely used in tissue engineering, drug delivery, medical devices and other fields.

3.1 Tissue Engineering Stent

MDA is copolymerized with biodegradable materials such as polylactic acid and polycaprolactone, which can generate tissue engineering scaffolds with good biocompatibility and controllable degradability. Such scaffolds can provide cells with a suitable growth environment and promote tissue regeneration and repair. For example, some tissue engineering scaffolds can improve cell adhesion and proliferation by regulating pore structure and surface morphology. In addition, by introducing growth factors or drugs, the stent can be provided with the function of directed inducing tissue regeneration and accelerated wound healing.

3.2 Drug Delivery System

MDA can be used as a drug carrier for the preparation of sustained-release or targeted drug delivery systems. For example, MDA can be copolymerized with materials such as polyvinyl alcohol and polyethylene glycol to produce microspheres or nanoparticles with controlled release characteristics. This type of drug delivery system can design different release curves according to the nature of the drug and treatment needs, extend the time of the drug’s action and improve the therapeutic effect. In addition, by introducing targeted molecules, the drug delivery system can be specifically identified and acted on the lesion site, reducing damage to normal tissue.

3.3 Medical device coating

MDA can be used to prepare medical device coatings with good biocompatibility and antibacterial properties. For example, MDA combined with polyurethane or silicone rubber materials can produce catheter coatings with excellent lubricity and anticoagulation properties, reducing friction resistance and blood clotting risks during surgery. In addition, by introducing antibacterial agents or photosensitive materials, the coating can have a long-term antibacterial function to prevent the occurrence of infection.

MDA’s future prospects and challenges

MDA, as a multifunctional organic compound, has shown great application potential in many fields. However, with the continuous development of technologyWith progress and changes in social needs, the research and development and application of MDA are also facing new opportunities and challenges. In the future, the development of MDA will mainly focus on the following aspects:

1. Breakthrough in green synthesis technology

With the increase in environmental awareness, traditional MDA synthesis methods have been difficult to meet the needs of modern society. The focus of future R&D will be on the development of greener and more efficient synthetic technologies. For example, using renewable resources as raw materials, developing new catalysts, optimizing reaction conditions, reducing waste generation, etc. In addition, the application of continuous production processes will further improve production efficiency and reduce production costs.

2. Expansion of new application fields

Although MDA has achieved certain results in the fields of high-performance materials, functional coatings, biomedical materials, etc., its application potential is far from fully tapped. In the future, researchers will continue to explore the application of MDA in emerging fields, such as smart materials, energy storage, environmental protection, etc. For example, MDA can be used to prepare smart materials with functions such as self-healing, shape memory, and responsiveness; it can also be used to develop high-performance battery electrolytes, supercapacitor electrode materials, etc.; it can also be used to prepare efficient adsorbents and catalysts and other environmentally friendly materials.

3. Multidisciplinary cross-fusion

The research and application of MDA involves multiple disciplines, such as chemistry, materials science, biology, physics, etc. Future R&D will pay more attention to the cross-integration of multidisciplinary disciplines and promote the innovative development of MDA technology. For example, by introducing cutting-edge technologies such as nanotechnology, gene editing technology, and artificial intelligence, new ideas and methods can be brought to the synthesis and application of MDA. In addition, interdisciplinary cooperation will promote collaborative innovation in MDA in different fields and form a more complete industrial chain and technology system.

4. Improvement of regulations and standards

As the scope of MDA application expands, relevant regulations and standards also need to be continuously improved. For example, the application of MDA in the fields of medicine, food, cosmetics, etc. requires strict safety assessment and supervision to ensure that its impact on human health and the environment is minimized. In addition, the production process of MDA also needs to comply with the requirements of environmental protection and sustainable development, and formulate corresponding emission standards and waste treatment specifications. In the future, governments and industry associations will strengthen the formulation and revision of relevant MDA regulations and standards to provide strong guarantees for the healthy development of MDA.

5. Market competition and cooperation

The competition in the MDA market is becoming increasingly fierce, and major companies are increasing their R&D investment to compete for the dominance of technology and market. In the future, the competition in the MDA industry will pay more attention to technological innovation and brand building, and enterprises need to continuously improve their R&D capabilities and market competitiveness. At the same time, international cooperation and exchanges will also become an important driving force for the development of MDA. By strengthening cooperation with enterprises and scientific research institutions in other countries and regions, resources can be shared and advantages can be complemented.Jointly promote the progress of MDA technology and the promotion of application.

Conclusion

4,4′-diaminodimethane (MDA) is a multifunctional organic compound. With its unique chemical structure and excellent properties, it has shown a wide range of application prospects in many fields. From the perspective of patented technology, MDA synthesis methods and application fields have been continuously innovated, forming a rich technological reserve. In the application of new materials, MDA has achieved great potential and brought new development opportunities to materials science. Looking ahead, the research and development and application of MDA will continue to face new challenges and opportunities. Breakthroughs in green synthesis technology, expansion of new application fields, cross-integration of multidisciplinary, improvement of regulations and standards, and market competition and cooperation will become the key to MDA’s development. direction. We look forward to MDA bringing more surprises and contributions to human society in the future.

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Physical and chemical properties of 4,4′-diaminodiphenylmethane and its detection methods in the laboratory

2月 18th, 2025 News

Introduction to 4,4′-Diaminodimethane

4,4?-diaminodiphenylmethane (4,4?-Diaminodiphenylmethane, referred to as DDM) is an important organic compound that is widely used in chemical industry, medicine and materials science fields. Its chemical formula is C13H12N2 and its molecular weight is 196.25 g/mol. The structure of DDM is characterized by the fact that two rings are bridged by a methylene and each ring contains an amino functional group. This unique structure gives it excellent chemical reactivity and physical properties, making it outstanding in a variety of applications.

From a historical perspective, the research on DDM can be traced back to the late 19th century. With the development of synthetic chemistry, people have gradually realized its potential value in polymers, dyes, drugs and other fields. Since the mid-20th century, the application scope of DDM has been further expanded, especially in high-performance resins, polyurethane foams and epoxy curing agents. Today, DDM has become one of the indispensable and important raw materials in industrial production.

In terms of chemical properties, DDM has high activity and can participate in many types of chemical reactions. For example, it can react with isocyanate to form polyurethane, react with epoxy resin to form a crosslinking network, and can also be used as a coupling agent to synthesize complex organic molecules. These characteristics make DDM have a wide range of application prospects in polymer materials, coatings, adhesives and other fields.

Next, we will discuss in detail the physical and chemical properties of DDM, including its basic parameters such as melting point, boiling point, solubility, and its stability under different conditions. Through an in-depth understanding of these properties, we can better grasp the behavioral laws of DDM, thereby providing a theoretical basis for its reasonable application.

Physical Properties

The physical properties of 4,4′-diaminodimethane (DDM) are crucial for their application in laboratories and industries. The following are some key physical parameters of DDM, presented in tabular form, which is convenient for readers to understand intuitively:

parameter name Symbol Unit value
Molecular Weight M g/mol 196.25
Melting point Tm °C 87-89
Boiling point Tb °C >300(Decomposition)
Density ? g/cm³ 1.16
Refractive index n – 1.61 (20°C)
Specific optometry [?] ° -1.5 (c = 1, CHCl?)

Melting point and boiling point

DDM has a melting point of 87-89°C, which means it is solid at room temperature but is prone to melting when heated. This characteristic makes it necessary to pay special attention to temperature control during certain processing processes to avoid unnecessary phase transitions. In contrast, DDM has a higher boiling point and decomposes over 300°C. Therefore, when using DDM under high temperature conditions, it is necessary to operate with caution to prevent its decomposition and produce harmful gases or affect product quality.

Density and Refractive Index

DDM has a density of 1.16 g/cm³, which is slightly higher than the density of water (1 g/cm³). This feature needs to be taken care of when handling and storing DDM as it may sink into water, resulting in uneven mixing. In addition, the refractive index of DDM is 1.61 (20°C), which is of great significance in optical analysis. By measuring the refractive index, the purity and concentration of the sample can be quickly judged, thereby ensuring the accuracy of the experimental results.

Solution

The solubility of DDM in different solvents is shown in the following table:

Solvent Solution
Water Insoluble
Slightly soluble
soluble
Dichloromethane Easy to dissolve
Trichloromethane Easy to dissolve
Tetrahydrofuran Easy to dissolve
A Easy to dissolve

As can be seen from the table, DDM has good solubility in organic solvents with less polarity, but in waterAlmost insoluble. This property makes DDM very useful in organic synthesis and polymer chemistry because it can react in a suitable solvent system without being affected by water. However, in practice, it is important to choose the right solvent, as different solvents may affect the reaction rate and the purity of the product.

Other physical properties

In addition to the above main physical parameters, DDM also has some other noteworthy physical properties. For example, its specific optical rotation is -1.5° (c = 1, CHCl?), indicating that it has some optical activity. Although DDM is not a chiral molecule itself, its derivatives may have chiral centers, which has potential application value in medicinal chemistry and asymmetric synthesis.

In addition, the thermal stability of DDM is also an important consideration. Studies have shown that DDM is relatively stable at room temperature, but is prone to decomposition at high temperatures. To improve its thermal stability, an appropriate amount of stabilizer is usually added to the reaction system or a lower reaction temperature is selected. For example, when preparing polyurethane foam, the reaction temperature is usually controlled between 80-100°C to ensure that the DDM does not decompose prematurely, thereby affecting the performance of the product.

In short, the physical properties of DDM determine its behavior in different application scenarios. Understanding these properties not only helps optimize experimental design, but also provides an important reference for industrial production. Next, we will explore the chemical properties of DDM in depth and further reveal its performance in the reaction.

Chemical Properties

4,4′-diaminodimethane (DDM) is an important organic compound and its chemical properties are particularly interesting. The molecular structure of DDM contains two active amino functional groups, which enables it to participate in multiple types of chemical reactions, showing a wide range of reactivity and versatility. The following are the main chemical properties of DDM and their application examples.

Active functional group

The two amino groups (-NH?) in the DDM molecule are their active functional groups. Amino groups are highly nucleophilic and alkaline, and can react with a variety of electrophilic reagents. For example, DDM can be added with electrophiles such as acid anhydride, acid chloride, isocyanate, etc. to generate corresponding amine compounds. In addition, the amino group can also react with other nitrogen-containing compounds such as nitro and nitroso to form more complex organic molecules.

Reaction with isocyanate

One of the famous applications of DDM is to react with isocyanate (R-NCO) to form polyurethane (PU). This reaction, known as the “ureaization reaction”, is a key step in the preparation of polyurethane foams, elastomers and coatings. The reaction process is as follows:

[ text{DDM} + 2 text{R-NCO} rightarrow text{R-NH-CO-NH-R} + text{NH?}]

In this process, the two amino groups of DDM react with two isocyanate groups respectively to form a stable urea bond (-NH-CO-NH-). Since DDM molecules contain two amino groups, it can act as a crosslinking agent to promote crosslinking between multifunctional isocyanates and form a three-dimensional network structure. This structure imparts excellent mechanical properties, chemical resistance and thermal stability to the polyurethane material.

Reaction with epoxy resin

DDM can also be reacted with epoxy resin (EP) and used as an epoxy curing agent. Epoxy resin is a polymer compound composed of bisphenol A and epoxy chloride, and has excellent mechanical strength and chemical resistance. However, the uncured epoxy resin is liquid at room temperature and cannot be directly applied to actual production. By adding DDM as the curing agent, the epoxy resin can undergo a cross-linking reaction to form a hard solid material.

The reaction mechanism of DDM and epoxy resin is as follows:

[ text{DDM} + text{EP} rightarrow text{crosslinked network} ]

In this process, the amino group of DDM undergoes a ring-opening addition reaction with the epoxy group (-O-CH?-CH?-O-) in the epoxy resin to form hydroxyl groups (-OH) and new carbon- Nitrogen bond. As the reaction progresses, multiple DDM molecules and epoxy resin molecules are connected together by covalent bonds to form a highly crosslinked three-dimensional network structure. This structure not only improves the hardness and strength of the material, but also gives it good heat resistance and chemical corrosion resistance.

Reaction with other electrophiles

In addition to reacting with isocyanate and epoxy resin, DDM can also react with other electrophiles. For example, DDM can react with acid anhydride (R?-COO-COR?) to form amide, react with acid chloride (R-COCl) to form amide, and react with aldehydes (R-CHO) to form imine. These reactions not only expand the scope of application of DDM, but also provide new ways to synthesize complex organic molecules.

Take the reaction between DDM and acid anhydride as an example, the reaction process is as follows:

[ text{DDM} + text{R?-COO-COR?} rightarrow text{R?-COO-NH-DDM} + text{COR?} ]

In this process, the amino group of DDM undergoes a nucleophilic addition reaction with the carbonyl group in the acid anhydride to form an amide bond (-CONH-). Since the DDM molecule contains two amino groups, it can react with multiple anhydride molecules to form a polyamide compound. This type of compound has a wide range of applications in pharmaceuticals, pesticides and polymer materials.

Stability and Decomposition

Although DDM has high reactivity, it is relatively stable at room temperature and is not prone to spontaneous decomposition. However, in high temperatures or strongUnder acid and strong alkali conditions, DDM may decompose, producing ammonia (NH?), formaldehyde and other by-products. For example, when the temperature exceeds 300°C, DDM will decompose quickly, releasing toxic gases, so special care is required when operating at high temperatures.

In order to improve the stability of DDM, an appropriate amount of stabilizers, such as antioxidants, ultraviolet absorbers, etc., are usually added to the reaction system. These stabilizers can effectively inhibit the oxidative degradation and photolysis reaction of DDM and extend its service life. In addition, choosing appropriate reaction conditions (such as low temperature, inert gas protection, etc.) can also reduce the risk of decomposition of DDM.

Acidal and alkaline properties

The amino group of DDM has a certain basicity and can neutralize and react with acidic substances. For example, DDM can react with inorganic acids such as hydrochloric acid and sulfuric acid to form corresponding salts. This property allows DDM to be used as a basic catalyst in certain catalytic reactions, promoting proton transfer and electron transfer. In addition, DDM can also react with organic acids (such as acetic acid, oxalic acid, etc.) to form amides or ester compounds, further expanding its application areas.

In short, the chemical properties of DDM make it a versatile organic compound that can play an important role in a variety of reactions. By rationally utilizing its active functional groups and reaction properties, more high-performance materials and chemicals can be developed. Next, we will explore the safety of DDM and its protective measures in the laboratory.

Safety and Protection Measures

4,4′-diaminodimethane (DDM) is widely used in industries and laboratories, but its chemical properties also bring certain safety risks. To ensure the health and safety of the experimenter, it is crucial to understand the safety of DDM and take appropriate protective measures.

Health Hazards

DDM belongs to aromatic amine compounds and has certain toxicity. Long-term exposure or inhalation of DDM may cause irritation symptoms in the respiratory system, skin and eyes. Specifically, DDM can cause the following health problems:

  1. Respiratory irritation: Inhaling DDM vapor or dust may cause symptoms such as cough, asthma, chest tightness, etc., and in severe cases, even bronchitis or lung diseases.
  2. Skin Irritation: DDM has a strong irritating effect on the skin, and allergic reactions such as redness, swelling, itching, and rash may occur after contact. Long-term contact may also cause problems such as dry skin and cracks.
  3. Eye irritation: When DDM vapor or liquid comes into contact with the eyes, it may cause symptoms such as eye pain, tears, blurred vision, etc., and in severe cases, it may lead to corneal damage.
  4. Carrectic Risk: Some studies show that aromatic amine compounds have potential carcinogenicitySexual, prolonged exposure to high concentrations of DDM environments may increase the risk of cancer, especially bladder and lung cancer.

Environmental Hazards

DDM also has certain harm to the environment. If accidentally leaked or discharged into the environment, DDM may contaminate soil, water and air, affecting the ecosystem. Specifically, DDM may cause toxicity to aquatic organisms and terrestrial plants, inhibiting their growth and reproduction. In addition, DDM is not easy to degrade in the environment and may accumulate in soil and water bodies, causing long-term environmental pollution.

Protective Measures

In order to effectively prevent the health and environmental risks brought by DDM, laboratories and industrial sites should take a series of protective measures. Here are some common protection suggestions:

  1. Ventiation System: In laboratories using DDM, effective ventilation equipment, such as fume hoods or local exhaust devices, should be installed to ensure air circulation and reduce the accumulation of harmful gases. Experimental personnel should operate in a well-ventilated environment to avoid inhaling DDM vapor.

  2. Personal Protective Equipment: Experimental personnel should wear appropriate personal protective equipment (PPE), including:

    • Gloves: Choose chemically resistant gloves, such as nitrile rubber gloves or neoprene gloves, to prevent direct contact with DDM in the skin.
    • Goops: Wear splash protection goggles or face masks to prevent DDM liquid or dust from entering the eyes.
    • Protective Clothing: Wear long-sleeved laboratory clothing or protective clothing to cover the whole body and avoid skin exposure.
    • Respiratory Protection: In high concentration environments, wear a filtered respirator or self-sufficient respirator to prevent inhalation of DDM vapor.

  3. Operational Procedures: Experimental personnel should strictly abide by the operating procedures to avoid unnecessary contact and exposure. For example, try to use airtight containers to store and transfer DDM to reduce volatility; when handling DDM, move gently to avoid dust or splash.

  4. Emergency treatment: The laboratory should be equipped with emergency treatment facilities, such as eye washers, emergency showers, etc., so as to clean the injured area in a timely manner when an accident occurs. In addition, the experimenter should be familiar with emergency plans and master the correct first aid measures, such as rinsing with a lot of water immediately after skin contact, rinsing with normal saline immediately after eye contact, and seek medical treatment as soon as possible.

  5. Waste LocationManagement: DDM’s waste should be disposed of in accordance with the treatment regulations for hazardous chemicals. Waste liquid, waste residue, etc. should be collected in a classified manner, sealed and stored, and entrusted with a qualified environmental protection company for professional treatment to avoid random discharge or dumping.

  6. Training and Education: The laboratory should conduct safety training for all personnel involved in DDM operations to ensure they understand the dangers and protective measures of DDM. Organize safety drills regularly to improve the emergency response capabilities of experimental personnel.

Regulations and Standards

All countries have strict regulations and standards for the use and management of DDM. For example, the EU’s Chemical Registration, Evaluation, Authorization and Restriction Regulations (REACH) requires companies to conduct a comprehensive safety assessment of DDM and take necessary risk control measures. The U.S. Environmental Protection Agency (EPA) also has regulations on the production and use of DDM to limit its emissions in the environment. China regulates the transportation, storage and use of DDM in accordance with the “Regulations on the Safety Management of Hazardous Chemicals”.

In short, although DDM is an important organic compound, its potential health and environmental risks cannot be ignored. By taking effective protective measures and complying with relevant regulations, the risks brought by DDM can be minimized and the safety and environmental protection of experimental personnel can be ensured. Next, we will introduce the detection methods of DDM in the laboratory to help researchers accurately determine its content and purity.

Laboratory Test Methods

The accurate detection of 4,4′-diaminodimethane (DDM) is crucial for experimental research and industrial production. Due to the complex chemical properties of DDM, choosing a suitable detection method can not only ensure the reliability of experimental results, but also improve work efficiency. The following are several commonly used DDM detection methods, covering from simple qualitative analysis to precise quantitative analysis, suitable for different experimental needs.

1. UV-visible spectrophotometry (UV-Vis)

UV-visible spectrophotometry is a simple, fast and sensitive detection method that is widely used in the qualitative and quantitative analysis of organic compounds. DDM has a specific absorption peak in the UV region, and its concentration can be determined by measuring its absorbance.

Principle

The aromatic rings and amino functional groups in DDM molecules have strong absorption capacity in the ultraviolet light region. Generally, the large absorption wavelength of DDM is between 230-260 nm. By drawing a standard curve, the concentration of DDM can be calculated based on the absorbance of the sample.

Operation steps
  1. Preparation of standard solutions: Take a certain amount of DDM standard products and dilute them with appropriate solvents (such as, dichloromethane, etc.) to a series of known concentrationsstandard solution.
  2. Measure absorbance: Use an UV-visible spectrophotometer to measure the absorbance of each standard solution at a selected wavelength, drawing a standard curve.
  3. Determination of the sample: Dilute the sample to be tested with the same solvent to the appropriate concentration, measure its absorbance, and calculate the concentration of DDM based on the standard curve.
Advantages
  • Simple operation, popular equipment, and low cost.
  • Fast measurement speed, suitable for preliminary screening of large batches of samples.
Disadvantages
  • For DDM in complex substrates, there may be interference and affect accuracy.
  • The appropriate solvent and wavelength need to be selected to avoid background absorption.

2. High Performance Liquid Chromatography (HPLC)

High performance liquid chromatography (HPLC) is a high-resolution separation technology suitable for quantitative analysis of DDM in complex samples. HPLC can effectively separate DDM from other impurities by selecting the appropriate stationary and mobile phases to obtain accurate detection results.

Principle

HPLC achieves separation based on the distribution differences between the stationary and mobile phases of the components in the sample. The aromatic rings and amino functional groups in DDM molecules have a good retention time on the reverse phase chromatography column, and can be quantitatively analyzed by ultraviolet detectors or fluorescence detectors.

Operation steps
  1. Chromatography column: C18 reverse phase chromatography column is usually used because it has a good separation effect on aromatic compounds.
  2. Select mobile phase: Select a suitable mobile phase combination, such as water-acetonitrile or water-methanol, according to the polarity and solubility of DDM.
  3. Injection Analysis: Inject the sample to be tested into the HPLC system, record the chromatogram, and calculate the content of DDM based on the retention time and peak area.
  4. Calibration Curve: Use DDM standards to prepare a series of standard solutions at known concentrations and draw calibration curves for quantitative analysis.
Advantages
  • High resolution, suitable for the separation and quantification of complex samples.
  • High sensitivity and low detection limit, suitable for the analysis of micro samples.
Disadvantages
  • The equipment is costly and the operation is relatively complicated.
  • The sample pre-processing is more cumbersome and may affectAnalytical efficiency.

3. Gas Chromatography-Mass Spectrometry Coupling (GC-MS)

Gas chromatography-mass spectrometry combined with GC-MS (GC-MS) combines the efficient separation ability of gas chromatography and the high sensitivity and specificity of mass spectrometry. It is currently one of the precise DDM detection methods. GC-MS can not only quantitatively analyze DDM, but also confirm its structure, and is particularly suitable for trace analysis and identification of unknown compounds.

Principle

GC-MS separates the components in the sample by gas chromatography and then ionizes and mass analysis through a mass spectrometer. DDM molecules have a specific retention time on gas chromatography columns, and their fragment ions have characteristic mass-to-charge ratios (m/z) in the mass spectrum, which can be qualitative and quantitatively analyzed based on these characteristics.

Operation steps
  1. Derivatization Treatment: Because DDM is highly polar, it is difficult to directly conduct gas chromatography analysis, and it is usually necessary to perform derivatization treatment. Commonly used derivatization reagents include trifluoroanhydride (TFAA), pentafluoropropionic anhydride (PFPA), etc. The derived DDM has better volatility and thermal stability.
  2. Chromatography Column: Choose a capillary chromatography column suitable for polar compounds, such as DB-5 or HP-5.
  3. Select ion source: Usually, electron bombardment ion source (EI) or chemical ionization source (CI) is used to select the appropriate ionization method according to experimental needs.
  4. Mass Spectrometry: Inject the derivatized sample into the GC-MS system, record the mass spectrum, and perform qualitative and quantitative analysis based on the characteristic ion peaks.
  5. Calibration Curve: Use derivatized DDM standards to prepare a series of standard solutions at known concentrations and draw calibration curves for quantitative analysis.
Advantages
  • Extremely high resolution and sensitivity, suitable for trace analysis.
  • Quantitative and quantitative analysis can be performed simultaneously, and the results are reliable.
  • Suitable for DDM detection in complex substrates, it has strong anti-interference ability.
Disadvantages
  • The equipment is expensive and complex, and requires professional technicians.
  • The sample pre-processing is more cumbersome, and the derivatization step may introduce errors.

4. Infrared Spectroscopy (IR)

Infrared spectroscopy (IR) is a molecular vibration-based analysis method suitable for structural identification and purity analysis of DDM. Functional groups in DDM molecules (such as amino groups, aromatic rings) There are characteristic absorption peaks in the infrared spectrum, and the presence and purity of DDM can be confirmed through these characteristic peaks.

Principle

Infrared spectroscopy uses the measurement of the absorption of molecules in the infrared light region to obtain its vibration frequency information. The amino group (-NH?) and aromatic ring (C=C) in DDM molecules have obvious absorption peaks in the infrared spectrum, which are 3300-3500 cm?¹ (N-H stretching vibration) and 1600-1650 cm?¹ (C= C telescopic vibration). By comparing the infrared spectrum of the sample with the spectra of the standard, the purity and structure of the DDM can be judged.

Operation steps
  1. Sample Preparation: Mix the DDM sample with KBr powder, press the tablet to make a transparent sheet, or directly coat it on ATR (attenuation total reflection) crystal.
  2. Measurement of spectra: Use a Fourier transform infrared spectrometer (FTIR) to scan the infrared spectrum of the sample in the range of 400-4000 cm?¹.
  3. Data Analysis: Compare the infrared spectrum of the sample with the spectrum of the DDM standard, confirm the position and intensity of the characteristic absorption peaks, and judge the purity and structure of the DDM.
Advantages
  • Simple operation and no complicated sample preprocessing is required.
  • It can quickly obtain molecular structure information and is suitable for purity analysis.
Disadvantages
  • Low sensitivity and is not suitable for trace analysis.
  • For DDM in complex substrates, there may be interference and affect accuracy.

5. Nuclear magnetic resonance spectroscopy (NMR)

Nuclear magnetic resonance spectroscopy (NMR) is an analytical method based on nuclear spins, suitable for structural confirmation and quantitative analysis of DDM. NMR can obtain detailed molecular structure information by measuring the resonance signals of hydrogen nuclei (¹H) or carbon nuclei (¹³C) in a molecule.

Principle

NMR obtains information such as chemical shift, coupling constant, etc. by measuring the resonance frequencies of different nuclei in a molecule. The hydrogen and carbon nuclei in DDM molecules have characteristic signal peaks in the NMR spectrum, and the structure and purity of DDM can be confirmed based on these signal peaks.

Operation steps
  1. Sample Preparation: Dissolve the DDM sample in an appropriate deuterated solvent, such as deuterated chloroform (CDCl?) or deuterated dimethyl sulfoxide (DMSO-d?).
  2. Measurement of spectra: Using a nuclear magnetic resonance spectrometer (NMR),Measure the ¹H NMR and ¹³C NMR spectrum of the sample at the appropriate magnetic field intensity.
  3. Data Analysis: Compare the NMR spectrum of the sample with the spectrum of the DDM standard, confirm the position and intensity of the characteristic signal peaks, and judge the structure and purity of the DDM.
Advantages
  • Structural information is rich and suitable for structural confirmation of complex molecules.
  • No derivatization treatment is required, and the sample loss is small.
Disadvantages
  • The equipment is expensive and complex, and requires professional technicians.
  • Low sensitivity and is not suitable for trace analysis.

Summary

4,4′-diaminodimethane (DDM) is an important organic compound and has a wide range of physicochemical properties and application prospects. This article introduces the physical properties, chemical properties, safety and protective measures of DDM in detail, and discusses a variety of laboratory testing methods. Through these contents, readers can have a comprehensive understanding of the characteristics of DDM and its applications in different fields.

The physical properties of DDM determine its behavior in different environments. Parameters such as melting point, boiling point, solubility and other parameters provide an important reference for experimental design. Its chemical properties give it a wide range of applications in various reactions, especially in crosslinking in polymer materials such as polyurethane and epoxy resin. However, the toxicity and environmental hazards of DDM cannot be ignored. Laboratory and industrial sites should take effective protective measures to ensure safe operation.

In the laboratory, choosing the appropriate assay is essential for the accurate determination of DDM content and purity. Ultraviolet-visible spectrophotometry, high performance liquid chromatography, gas chromatography-mass spectrometry, infrared spectrometry and nuclear magnetic resonance spectrometry have their own advantages and disadvantages and are suitable for different experimental needs. Researchers can choose suitable detection methods based on specific experimental conditions and purposes to obtain reliable experimental results.

In short, DDM, as a versatile organic compound, plays an important role in modern chemistry and materials science. By deeply understanding its physical and chemical properties and detection methods, we can better utilize the advantages of DDM and promote innovative development in related fields.

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