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Methylene bisacrylamide, also known as bisacrylamide, is a white crystalline powder, odorless, with the molecular formula C7H10N2O2 and CAS 110-26-9. Highly hygroscopic, slightly soluble in organic solvents such as water, ethanol, acetone, etc., soluble in acrylamide, forming acrylamide bisacrylamide solution. NN bisacrylamide and NN are amine organic compounds with similar uses and are widely used in chemical reagents. The production of thickeners and adhesives for the textile industry, the production of sealing agents for oil extraction, as well as many fields such as leather, chemical industry, printing, etc. Stay away from oxidants, strong alkalis, heat sources, and direct sunlight.
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Chemical Formula |
C7H10N2O2 |
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Exact Mass |
154 |
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Molecular Weight |
154 |
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m/z |
154 (100.0%), 155 (7.6%) |
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Elemental Analysis |
C, 54.54; H, 6.54; N, 18.17; O, 20.76 |
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Melting point > 300 ° C (lit.), Boiling point 277.52 ° C (rough estimate), Density 1.235, Vapor density 5.31 (vs air), Refractive index 1.4880 (estimated), Storage conditions 2-8 ° C, Solubility H2O: 20 mg / ml at 20 ° C, clear, colorless, Morphological powder, Acidity coefficient (PKA) 13.07 ± 0.46 (predicted), Color white, Odor odorless, Acid base indicator discoloration pH range > 5, PH value > = 5.0 (25g / L, H2O, 20 ℃), Water solubility 0.01-0.1 g / 100 ml at 18 º C, Air & light sensitive, Maximum wavelength(λ max)528nm(H2O)(lit.), BRN 1706297, InChIKeyZIUHHBKFKCYYJD-UHFFFAOYSA-N.
Methylene bisacrylamide (MBA) is an important organic compound with the molecular formula C ₇ H ₁ N ₂ O ₂ and a molecular weight of 154.16. As a double acrylamide crosslinking agent, the two acrylamide groups in its molecular structure can form a three-dimensional network structure through free radical polymerization, which makes it a key raw material in various fields such as biochemistry, materials science, petroleum engineering, textile printing and dyeing, and environmental protection.
1. Polyacrylamide gel electrophoresis (PAGE)
MBA is the core crosslinking agent of SDS-PAGE (sodium dodecyl sulfate polyacrylamide gel electrophoresis). By adjusting the molar ratio of MBA to acrylamide (typical ratio is 1:29), the porosity of gel can be precisely controlled. The concentration of separating gel is usually set at 7% -15%, where the concentration of MBA directly affects the migration rate of protein: the higher the concentration, the greater the cross-linking density of gel, and the migration of small molecule protein is blocked more significantly. For example, in RNA sample analysis, denatured polyacrylamide gel electrophoresis combined with MBA cross-linking system can achieve single nucleotide level resolution and provide key technical support for gene expression research.
Separation and purification of biomolecules
In the field of protein purification, MBA cross-linked polyacrylamide gel is used for matrix preparation of affinity chromatography and ion exchange chromatography. Its three-dimensional network structure can provide high specific surface area and achieve efficient capture of target proteins through electrostatic interactions or specific ligand binding. For example, in the antibody purification process, MBA cross-linked gel can improve the purity of the target antibody to more than 98%, with a recovery rate of 90%.
1. Highly Absorbent Resin (SAR)
MBA as a crosslinking agent can significantly enhance the water absorption and retention performance of resins. In the production of agricultural water retaining agents, using potato starch and acrylamide as raw materials, the MBA cross-linking system can increase the water absorption rate of the resin by 500-800 times, and extend the water slow-release period to 30 days in soil improvement in arid areas. In the field of hygiene products, the MBA cross-linked polymer network structure increases the liquid absorption capacity of diapers by 40 times their own weight, while maintaining a dry surface.
2. Hydrogel material
The intelligent hydrogel prepared by copolymerization of MBA and acrylamide shows unique advantages in the field of drug controlled release.
Its pH responsive network structure can accelerate the release rate of drugs in acidic tumor environments (pH 5.0-6.5) by 3-5 times compared to neutral environments (pH 7.4), significantly improving chemotherapy targeting. In tissue engineering, MBA cross-linked polyvinyl alcohol/chitosan composite hydrogel scaffold has a porosity of more than 90%, which supports the proliferation and differentiation of osteoblasts and can induce the formation of new bone tissue within 4 weeks.
3. High temperature resistant and fire-resistant materials
The phenolic resin based fire-resistant glass synthesized by MBA can maintain structural integrity at a high temperature of 1000 ℃, and its cross-linking density increases the thermal decomposition temperature from 350 ℃ to 520 ℃. This material has been applied to the construction of fire isolation zones in subway tunnels and has passed the GB/T 23932-2009 standard test, with a fire resistance limit of 120 minutes.
1. Water blocking and profile control agent
In oilfield water injection development, MBA cross-linked polyacrylamide gel system can selectively seal high permeability layers. On site applications have shown that in formations with a permeability difference of up to 10 times, this system can increase recovery by 8% -12%. Its gel strength can reach 5000-10000 mPa · s, and it is stable for more than 6 months at 90 ℃ formation temperature.
2. Fracturing fluid thickener
The methylene bisacrylamide crosslinked guar gum based fracturing fluid has a viscosity retention rate of over 80% at a shear rate of 170s ⁻¹, and its sand carrying capacity is significantly better than that of linear polymer systems.
In shale gas development, this system can increase fracture conductivity by 30% and single well production by 15% -20%.
3. Drilling fluid plugging material
MBA cross-linked cellulose nanocrystals/polyacrylamide composite materials can form a sealing layer for fractured formations. Laboratory tests have shown that the material can achieve a sealing pressure of 15MPa in 0.5-5mm cracks, reduce leakage by more than 95%, and significantly reduce non production time.
1. Thickener for paint printing
The all water phase thickener prepared by copolymerization of MBA with acrylamide and butyl acrylate can increase the viscosity of printing ink to 5000-10000 mPa · s, achieving high-precision printing (line width ≤ 0.1mm). Compared with traditional thickeners, this system can reduce dye usage by 15% and improve color fastness by 0.5-1 levels.
2. Fabric functional finishing agent
In the thermosetting pretreatment process, MBA cross-linked polyurethane coating can increase the water pressure resistance of cotton fabric to 2000mmH ₂ O, while maintaining breathability of ≥ 5000 g/(m ² · 24h).
This technology has been applied to the production of outdoor sportswear, and the product has passed the AATCC 22-2017 spray test with a waterproof rating of 4-5.
Flame retardant finishing agent
After treatment with MBA cross-linked phosphorus nitrogen flame retardants, the limit oxygen index (LOI) of polyester fabrics can be increased from 20% to 32%, and the vertical combustion grade can reach UL94 V-0 level. After 50 washes, the flame retardant performance retention rate still exceeds 85%, meeting the requirements of GB 8965.1-2020 standard.
1. Sewage treatment flocculant
MBA cross-linked cationic polyacrylamide can increase COD removal rate to 85% -90% and chromaticity removal rate to over 95% in the treatment of printing and dyeing wastewater. The quaternary ammonium groups on its molecular chain can quickly coagulate micrometer sized suspensions through charge neutralization and bridging, increasing the settling speed of flocs by 3-5 times.
2. Soil remediation materials
In the remediation of heavy metal contaminated soil, the MBA cross-linked sodium alginate/bentonite composite material has adsorption capacities of 256mg/g and 189mg/g for Pb ² ⁺ and Cd ² ⁺, respectively.
Through ion exchange and complexation, this material can reduce the available heavy metal content in soil by 80% -90%, meeting the GB 15618-2018 agricultural land soil pollution risk control standards.
3. Chemical resistance reducing agent
The conductive polymer prepared by copolymerization of MBA with acrylamide and sodium chloride can reduce soil resistivity from 1000 Ω· m to below 10 Ω· m in grounding engineering. On site testing shows that the durability of the material's drag reduction effect is over 15 years, significantly better than traditional drag reduction agents (3-5 years).
1. 3D printing materials
Methylene bisacrylamide cross-linked photocurable resin has a printing accuracy of up to 20 μ m and can be used to manufacture high-precision devices such as microfluidic chips and optical lenses. In biological 3D printing, the mechanical properties (compression modulus 0.1-1MPa) of MBA crosslinked gelatin/methylacrylamide hydrogel scaffold match with natural cartilage tissue to support three-dimensional growth of chondrocytes.
2. Energy storage materials
MBA cross-linked polyacrylamide based electrolytes can increase ion conductivity to 10 ⁻ S/cm in lithium-ion batteries while inhibiting lithium dendrite growth.
In the field of supercapacitors, as a gel electrolyte, this material can increase the energy density of devices by 30%, and the cycle life can reach more than 100000 times.
3. Intelligent response materials
The intelligent hydrogel prepared by copolymerization of MBA and temperature sensitive monomer N-isopropylacrylamide can undergo reversible swelling shrinkage under temperature stimulation. This material achieves pulsed release in drug controlled release systems, and under simulated human temperature changes (32-37 ℃), the fluctuation amplitude of drug release reaches 80%, providing a new solution for precision medicine.
There are four synthetic methods of n-methylenebisacrylamide:
Acrylonitrile reacts with formaldehyde in water under the catalysis of sulfuric acid to synthesize methylenebisacrylamide sulfate. After being neutralized by ammonia, N, N ~ methylenebisacrylamide is separated out. After washing with water and drying, the product n, n-methylenebisacrylamide is obtained. The reaction formula is as follows:
2CH2-CHCN+HCHO+H20+H2S04 → (CH2=CHCONH2)2CH2H2SO4
(CH2=CHCONH2)2CH2H2SO4+2NH3 → (CH2=CHCONH2)2CH2+(NH4)2S04
Acrylamide and formaldehyde react in water or organic solvent under the catalysis of strong acid. After the reaction is completed, they are neutralized with ammonia water, precipitated, cooled, washed, dehydrated and dried, and then refined to obtain n, n-methylbisacrylamide. The reaction is as follows:
HCH2-CHCONH+HCHOCH2-CHCONHCHOHCTI2-CHCONHCH2OH+CH2-CHCONH → (CH2=CHCONH)2CH2+H20
Acrylamide and paraformaldehyde react in an organic solvent under the catalysis of acid. After the reaction is completed, the temperature is lowered, filtered and dried to obtain crude n, n-methylenebisacrylamide, which is refined by 6O% ethanol to obtain the product n, n-methylenebisacrylamide. The reaction formula is as follows:
H2C-CHCONH2+(CHO0CH2CHCON-CNHCH2OHCH2-CHCONHCH2OH+CH2--CHCONH2 → (CH2CHCONH)2CH2+H20
N, n-methylenebisacrylamide is formed by the reaction of n-hydroxymethylbisacrylamide and bisacrylamide under acidic conditions. The reaction formula is as follows:
CH2=CHCONHCH2OH+CH2=CHCONH2- → (CH2=CHCONH2)2CH2+H20
From the above four synthetic routes, we can see that:
The first synthesis route is the earliest methylene bisacrylamide method used for industrialization at home and abroad. This process is not suitable for the complex process, long production cycle, large equipment investment and large amount of sulfuric acid, which is easy to cause corrosion to the equipment. Moreover, the purity of the product is not high, the content is only 90%, and the relative cost is high. In addition, the main raw material acrylonitrile is flammable, explosive and highly toxic;
The second synthetic route eliminates the flammable and explosive raw materials in the above method, and the purity of the product is also improved, but it is not more than 95%, which is difficult to meet the market demand;
The third synthetic route is simple in process, convenient in operation, short in production cycle, small in equipment investment, high in yield (more than 80%), high in purity (more than 98%), easy to treat, solvent can be recycled, and the relative cost is low. It is a process route of great development value; The fourth synthetic route is not suitable because of high raw material cost and low relative profit.
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