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2-Acrylamido-2-methyl-1-propanesulfonic acid is a reactive, hydrophilic, sulfonic acid acrylic monomer used to alter the chemical properties of wide variety of anionic polymers.
In the 1970s, the earliest patents using this monomer were filed for acrylic fiber manufacturing.
CAS Number: 15214-89-8
EC Number: 239-268-0
IUPAC Name: 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid
Chemical Formula: C7H13NO4S
Other names: AtBS, acryloyldimethyltaurine, DTXSID5027770, LUBRIZOL AMPS, TBAS-Q, 1-Propanesulfonic acid, 2-acrylamido-2-methyl-, DTXCID207770, tert-butylacrylamidosulfonic acid, acrylamide tert-butylsulfonic acid, acrylamidomethylpropanesulfonic acid, 2-acrylamido-2-methylpropylsulfonic acid, 2-ACRYLAMIDO-2,2-DIMETHYLETHANESULFONIC ACID, 239-268-0, 15214-89-8, 2-Acrylamido-2-methylpropanesulfonic acid, 2-Acrylamide-2-methylpropanesulfonic acid, 2-acrylamido-2-methylpropane-1-sulfonic acid, 1-Propanesulfonic acid, 2-methyl-2-[(1-oxo-2-propenyl)amino]-, 2-Acrylamido-2-methylpropanesulfonate, 2-Acrylamido-2-methylpropanesulphonic acid, 2-methyl-2-(prop-2-enoylamino)propane-1-sulfonic acid, 490HQE5KI5, 2-methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid, 1-Propanesulfonic acid, 2-methyl-2-((1-oxo-2-propenyl)amino)-, 2-(acryloylamino)-2-methylpropane-1-sulfonic acid, 1-Propanesulfonic acid, 2-methyl-2-((1-oxo-2-propen-1-yl)amino)-, CAS-15214-89-8, EINECS 239-268-0, 2-ACRYLAMIDO-2-METHYLPROPANE SULFONIC ACID, UNII-490HQE5KI5, MFCD00007522, EC 239-268-0, 2-Acrylamido-2-methylpropanesulfonic acid (AMPS), SCHEMBL19490, 2-Acryloylamido-2-methylpropanesulfonic acid monomer, CHEMBL1907040, CHEBI:166476, Tox21_201781, Tox21_303523, AKOS015898709, CS-W015266, 5165-97-9 (mono-hydrochloride salt), NCGC00163969-01, NCGC00163969-02, NCGC00257492-01, NCGC00259330-01, 2-acrylamido-2-methyl propanesulfonic acid, 2-acrylamido-2-methyl propyl sulfonic acid, 2-acrylamido-2-methyl-propane sulfonic acid, 2-Acrylamido-2-methyl-1-propanesulfonicacid, 2-Acryloylamido-2-methylpropanesulfonic acid, A0926, NS00005061, 2-ACRYLAMIDO-2-METHYLPROPIONESULFONATE, E76045, Q209301, 2-Acrylamido-2-methyl-1-propanesulfonic acid, 8CI, 2-Acrylamido-2-methyl-1-propanesulfonic acid, 99%, 2-methyl-2-(prop-2-enamido)propane-1-sulfonic acid, 2-(Acryloylamino)-2-methyl-1-propanesulfonic acid #, 2-methyl-2-(prop-2-enoylamino)propane-1-sulonic acid, 82989-71-7, InChI=1/C7H13NO4S/c1-4-6(9)8-7(2,3)5-13(10,11)12/h4H,1,5H2,2-3H3,(H,8,9)(H,10,11,12)
Today, there are over several thousands patents and publications involving use of AMPS in many areas including water treatment, oil field, construction chemicals, hydrogels for medical applications, personal care products, emulsion coatings, adhesives, and rheology modifiers. Lubrizol discontinued the production of this monomer in 2017 due to copy-cat production from China and India destroying the profitability of this product.
APPLICATIONS
Acrylic fiber: A number of enhanced performance characteristics are imparted to acrylic, modified-acrylic, polypropylene and polyvinylidene fluoride fibers: dye receptivity, moisture absorbency, and static resistance.
Coating and adhesive: Its sulfonic acid group gives the monomers ionic character over a wide range of pH.
Anionic charges from 2-Acrylamido-2-methyl-1-propanesulfonic acid fixed on polymer particles enhance the chemical and shear stabilities of polymer emulsion and also reduce the amount of surfactants leaching out of paint film.
2-Acrylamido-2-methyl-1-propanesulfonic acid improves the thermal and mechanical properties of adhesives, and increases the adhesive strength of pressure-sensitive adhesive formulations.
Detergents: Enhances the washing performance of surfactants by binding multivalent cations and reducing dirt attachment.
Personal care: Strong polar and hydrophilic properties introduced to a high molecular weight 2-Acrylamido-2-methyl-1-propanesulfonic acid homopolymer are exploited as a very efficient lubricant characteristic for skin care.
Medical hydrogel: High water-absorbing and swelling capacity when 2-Acrylamido-2-methyl-1-propanesulfonic acid is introduced to a hydrogel are keys to medical applications.
Hydrogel with 2-Acrylamido-2-methyl-1-propanesulfonic acid showed uniform conductivity, low electrical impedance, cohesive strength, appropriate skin adhesion, and biocompatible and capable of repeated use and have been used to electrocardiograph (ECG) electrodes, defibrillation electrode, electrosurgical grounding pads, and iontophoretic drug delivery electrodes.
In addition, polymers derived from 2-Acrylamido-2-methyl-1-propanesulfonic acid are used as the absorbing hydrogel and the tackifier component of wound dressings.
2-Acrylamido-2-methyl-1-propanesulfonic acid Is used due to its high water absorption and retention capability as a monomer in superabsorbents e. g. for baby diapers.
Oil field applications: Polymers in oil field applications have to stand hostile environments and require thermal and hydrolytic stability and the resistance to hard water containing metal ions.
For example, in drilling operations where conditions of high salinity, high temperature and high pressure are present, 2-Acrylamido-2-methyl-1-propanesulfonic acid copolymers can inhibit fluid loss and be used in oil field environments as scale inhibitors, friction reducers and water-control polymers, and in polymer flooding applications.
Water treatment applications: The cation stability of the 2-Acrylamido-2-methyl-1-propanesulfonic acid-containing polymers are very useful for water treatment processes.
Such polymers with low molecular weights cannot only inhibit calcium, magnesium, and silica scale in cooling towers and boilers, but also help corrosion control by dispersing iron oxide.
When high molecular weight polymers are used, they can be used to precipitate solids in the treatment of industrial effluent stream.
Crop protection: 2-Acrylamido-2-methyl-1-propanesulfonic acid increases in dissolved and nanoparticulate polymer formulations bioavailability of pesticides in aqueous-organic formulations.
Membranes: 2-Acrylamido-2-methyl-1-propanesulfonic acid increases water flow, retention and fouling resistance of asymmetric ultrafiltration and microfiltration membranes and is being studied as an anionic component in polymer fuel cell membranes.
Construction applications: Superplasticizers with 2-Acrylamido-2-methyl-1-propanesulfonic acid are used to reduce water in concrete formulations.
Benefits of these additives include improved strength, improved workability, improved durability of cement mixtures.
Redispersible polymer powder, when 2-Acrylamido-2-methyl-1-propanesulfonic acid is introduced, in cement mixtures control air pore content and prevent agglomeration of powders during the spray-drying process from the powder manufacturing and storage.
Coating formulations with 2-Acrylamido-2-methyl-1-propanesulfonic acid-containing polymers prevent calcium ions from being formed as lime on concrete surface and improve the appearance and durability of coating.
Water treatment: The 2-Acrylamido-2-methyl-1-propanesulfonic acid monomer homopolymer with the acrylamide acrylic acid monomer homopolymer, they could besludge dehydrating agent in the sewage purification process and preservative of the iron,zinc,aluminum,cooper,alloy in the closed water circulation system, they also could be used ascleaning and scale inhibitor of heatercoolingtowerair cleanerg-cleaner.
Oilfield chemistry: 2-Acrylamido-2-methyl-1-propanesulfonic acid is rapid development in the application of the oil field chemistry.
The scope including oil well cement admixtures drilling fluid additive acidizing fluid well completion fluid,work over fluid,fracture fluid.
Synthetic fiber: The 2-Acrylamido-2-methyl-1-propanesulfonic acid is the important monomer which could change the combination property of some synthetic fiber, in particular, the orion and the modacrylic fiber with chloride, the dosage is the 1-4 of the fiber, it could improve the white contentdyeing property ntistaticventilation property and flame resistance.
The sizes of the textile: The copolymer of the acrylami-2-methylpropane sulfonic acid, ethyl acetate and acrylic acid, it is the ideal size of the cotton and the polyester blend fabric, it has the characteristic of easy to use and east to use the water to remove.
Paper making: The copolymer of the acrylamide2methylpropane sulfonic acid with other watersoluble monomer, this is the indispensable chemical in all kinds of papermaking factory, it could be used as the drainage aid and on gel, it could increase the strength of the paper, it also could be used as the pigment dispersing agent of color coating.
2-Acrylamido-2-methyl-1-propanesulfonic acid monomer has a wide variety of uses including textiles, flocculants, dispersants, scale control agents as well as well-additives.
2-Acrylamido-2-methyl-1-propanesulfonic acid also has uses in water treatment agents (majorly as a scale preventing agent), paper and pulp industry, paint and coatings, good additives, acrylic fibre dyeing aids.
2-Acrylamido-2-methyl-1-propanesulfonic acid has an excellent synthesis, surface activity, absorptivity, biological activity, hydraulic as well as thermal stability.
The use of 2-Acrylamido-2-methyl-1-propanesulfonic acid monomers is diversified in areas including oil fields, construction chemicals, hydrogens for chemicals, adhesives and rheology modifiers, emulsion coatings and personal care products.
2-Acrylamido-2-methyl-1-propanesulfonic acid is suitable for use in co-polymerization and in addition reactions. It is popularly used in water treatment, latex adhesives and acrylic fibres.
DESCRIPTION
2-Acrylamido-2-methyl-1-propanesulfonic acid (AMPS) was a Trademark name.
2-Acrylamido-2-methyl-1-propanesulfonic acid is a reactive, hydrophilic, sulfonic acid acrylic monomer used to alter the chemical properties of wide variety of anionic polymers.
In the 1970s, the earliest patents using this monomer were filed for acrylic fiber manufacturing.
Today, there are over several thousands patents and publications involving use of 2-Acrylamido-2-methyl-1-propanesulfonic acid in many areas including water treatment, oil field, construction chemicals, hydrogels for medical applications, personal care products, emulsion coatings, adhesives, and rheology modifiers.
2-Acrylamido-2-methylpropanesulfonic acid for synthesis.
CAS 15214-89-8, chemical formula CH₃C(CH₂=CHCONH)(CH₃)CH₂SO₃H.
2-Acrylamido-2-methyl Propanesulfonic Acid, also known as 2-Acrylamido-2-methyl-1-propanesulfonic acid, is a sulfonic acid acrylic monomer used to change the chemical properties of anionic polymers.
Ungraded products are indicative of a grade suitable for general industrial use or research purposes and typically are not suitable for human consumption or therapeutic use.
2-Acrylamido-2-methyl-1-propanesulfonic acid (AMPS) is an fda approved for use in polymer components of food-contact paper and board adhesive.
Poly(2-acrylamido-2-methyl-1-propanesulfonic acid)(PAMPS)] has been found to inhibit the cytopathicity of HIV-1 and HIV-2 in MT-4 cells at concentrations that are not toxic to the host cells.
2-Acrylamido-2-methyl-1-propanesulfonic acid also inhibited syncytium formation in co-cultures of MOLT-4 cells with HIV-1- or HIV-2-infected HUT-78 cells.
2-Acrylamido-2-methyl-1-propanesulfonic acid inhibited binding of anti-gp120 mAb to HIV-1 gp120 and blocked adsorption of HIV-1 virions to MT-4 cells.
PROPERTIES
Hydrolytic and thermal stability: The geminal dimethyl group and the sulfomethyl group combine to sterically hinder the amide functionality and provide both hydrolytic and thermal stabilities to 2-Acrylamido-2-methyl-1-propanesulfonic acid-containing polymers.
Polarity and hydrophilicity: The sulfonate group gives the monomer a high degree of hydrophilicity and anionic character at wide range of pH.
In addition, 2-Acrylamido-2-methyl-1-propanesulfonic acid is absorbing water readily and also imparts enhanced water absorption and transport characteristics to polymers.
Solubility: 2-Acrylamido-2-methyl-1-propanesulfonic acid is very soluble in water and dimethylformamide (DMF) and also shows limited solubility in most polar organic solvents.
Inhibition of divalent cation precipitation: Sulfonic acid in 2-Acrylamido-2-methyl-1-propanesulfonic acid is a very strong ionic group and ionizes completely in aqueous solutions.
In applications where the precipitation of mineral salts is undesirable, the incorporation of a polymer containing even a small quantity of 2-Acrylamido-2-methyl-1-propanesulfonic acid can significantly inhibit the precipitation of divalent cations.
The result is a significant reduction in the precipitation of a wide variety of mineral salts, including calcium, magnesium, iron, aluminum, zinc, barium and chromium.
Determining viscosity-average molecular weight (Mark-Houwink constants).
Reactivity ratio: 2-Acrylamido-2-methyl-1-propanesulfonic acid reacts well with a variety of vinyl monomers.
PRODUCTION
2-Acrylamido-2-methyl-1-propanesulfonic acid is made by the Ritter reaction of acrylonitrile and isobutylene in the presence of sulfuric acid and water.
The recent patent literature describes batch and continuous processes that produce 2-Acrylamido-2-methyl-1-propanesulfonic acid in high purity (to 99.7%) and improved yield (up to 89%, based on isobutene) with the addition of liquid isobutene to an acrylonitrile / sulfuric acid / phosphoric acid mixture at 40°C.
