Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 2-Acrylamido-2-methylpropane sulfonic acid: Difference between pages

| Watchedfields = changed

| verifiedrevid = 477198056

| ImageAlt = Skeletal formula of AMPS

| ImageFile1 = AMPS-3D-spacefill.png

| ImageAlt1 = Space-filling model of the AMPS molecule

| PIN = 2-Methyl-2-(prop-2-enamido)propane-1-sulfonic acid

|Section1={{Chembox Identifiers

| PubChem = 65360

| EC_number = 925-482-8

| UNII = 490HQE5KI5

| ChEMBL = 1907040

|Section2={{Chembox Properties

| C=7 | H=13 | N=1 | O=4 | S=1

|Section3={{Chembox Hazards

| AutoignitionPt =

| NFPA-H = 3

| NFPA-F = 0

| NFPA-R = 1

| NFPA-S =

'''2-Acrylamido-2-methylpropane sulfonic acid''' ('''AMPS''') was a Trademark name by The Lubrizol Corporation. It 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 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.

== Production ==

AMPS is made by the [[Ritter reaction]] of [[acrylonitrile]] and [[isobutylene]] in the presence of [[sulfuric acid]] and water.<ref>

{{patent|US|3506707|"Preparation of acrylamidoalkanesulfonic acids." Inventors: Leonard E Miller, Donald L Murfin}}</ref> The recent patent literature<ref>{{patent|US|6504050|" Process for the preparation of 2-acrylamido-2-methyl-1-propanesulfonic acid." Inventors: P.P. Barve et al.}}</ref> describes batch and continuous processes that produce AMPS 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.

== 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 AMPS-containing polymers.<ref>W. O. Parker Jr and A. Lezzi, Polymer, 34(23), 4913 (1993)</ref><ref>{{cite journal |last=Aggour |first=Y. A. |date=1994-01-01 |title=Thermal degradation of copolymers of 2-acrylamido-2-methylpropanesulphonic acid with acrylamide |url=https://dx.doi.org/10.1016/0141-3910%2894%2990034-5 |journal=Polymer Degradation and Stability |volume=44 |issue=1 |pages=71–73 |doi=10.1016/0141-3910(94)90034-5 |issn=0141-3910}}</ref><ref>{{cite journal |last=Aggour |first=Y. A. |date=1998-01-01 |title=Investigation of the thermal degradation and stability of copolymers of 2-acrylamido-2-methylpropanesulphonic acid and methyl methacrylate |url=https://www.sciencedirect.com/science/article/pii/S0141391097000852 |journal=Polymer Degradation and Stability |volume=60 |issue=2 |pages=317–320 |doi=10.1016/S0141-3910(97)00085-2 |issn=0141-3910}}</ref><ref>Y. A. Aggour, "Copolymerization and thermal investigation of 2-acrylamido-2-methylpropane sulfonic acid with acrylonitrile", J. Polym. Mater. 17, 193 (2000)</ref>

* Polarity and hydrophilicity: The sulfonate group gives the monomer a high degree of [[hydrophilicity]] and anionic character at wide range of pH. In addition, AMPS is absorbing water readily and also imparts enhanced water absorption and transport characteristics to polymers.<ref>{{cite journal |last=Atta |first=Ayman M. |date=August 2002|title=Swelling behaviors of polyelectrolyte hydrogels containing sulfonate groups |url=https://onlinelibrary.wiley.com/doi/10.1002/pat.226 |journal=Polymers for Advanced Technologies |language=en |volume=13 |issue=8 |pages=567–576 |doi=10.1002/pat.226 |issn=1042-7147}}</ref>

* Solubility: AMPS is very soluble in water and dimethylformamide (DMF) and also shows limited solubility in most polar organic solvents.<ref>Lubrizol technical bulletin</ref>

{| class="wikitable" border="1"

|-

! Solvent

! Solubility (gAMPS/100 g solvent)

|-

| Water

| 150

|-

| [[Dimethylformamide]]

| >100

|-

| [[N-Methyl-2-pyrrolidone]]

| 80

|-

| [[Methanol]]

| 8.7

|}

* Inhibition of divalent cation precipitation: Sulfonic acid in AMPS 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 AMPS 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, aluminium, zinc, barium and chromium.<ref>{{cite journal |last1=Liu |first1=Yang |last2=Xie |first2=Jian-Jun |last3=Zhang |first3=Xin-Ying |date=2003-12-20 |title=Synthesis and properties of the copolymer of acrylamide with 2-acrylamido-2-methylpropanesulfonic acid |url=https://onlinelibrary.wiley.com/doi/10.1002/app.13003 |journal=Journal of Applied Polymer Science |language=en |volume=90 |issue=13 |pages=3481–3487 |doi=10.1002/app.13003 |issn=0021-8995}}</ref><ref>{{cite journal |last1=Rivas |first1=Bernabé L. |last2=Pooley |first2=S. Amalia |last3=Luna |first3=Maribel |last4=Geckeler |first4=Kurt E. |date=2001-10-03 |title=Synthesis of water-soluble polymers containing sulfonic acid and amine moieties for the recovery of metal ions using ultrafiltration |url=https://onlinelibrary.wiley.com/doi/10.1002/app.1819 |journal=Journal of Applied Polymer Science |language=en |volume=82 |issue=1 |pages=22–30 |doi=10.1002/app.1819 |issn=0021-8995}}</ref>

* Determining viscosity-average molecular weight (Mark-Houwink constants)<ref>J. S. Tan, L. W. Fisher, and P. Markus, "Effects of polymer structure on dilute-solution properties", ACS National Meeting in Philadelphia, Division of Organic Coating and Plastics Preprints, 35(1), 348 (1975)</ref>

{| class="wikitable" border="1"

|-

! Na-AMPS

! 0.01N

! 0.05N

! 0.1N

! 0.5N

! 1.0N

! 5.0N

|-

| K x 10⁵

| 0.67

| 1.47

| 1.67

| 1.32

| 3.34

| 5.01

|-

| ν

| 1.02

| 0.91

| 0.88

| 0.86

| 0.77

| 0.72

|}

* Reactivity ratio:<ref>Lubrizol Specialty Monomers technical brochure</ref> AMPS reacts well with a variety of vinyl monomers. M₂= AMPS or ^† sodium salt of AMPS

{| class="wikitable" border="1"

|-

! M₁

! r₁

! r₂

! Remark

|-

| [[Acrylonitrile]]

| 1.2

| 0.7

| [[Dimethylformamide|DMF]]

|-

| [[Acrylic acid]]

| 0.74

| 0.19

| Water, pH=7.0

|-

| [[Acrylic acid]]

| 1.58

| 0.11

| Water, pH=2~4

|-

| [[Itaconic acid]]

| 0.46

| 0.04

| [[Dimethylformamide|DMF]], 70&nbsp;°C, [[Benzoyl Peroxide]]

|-

| [[Acrylamide]]

| 0.98

| 0.49 ^†

| Water, K₂S₂O₈

|-

| [[Styrene]]

| 1.13

| 0.31

| [[Dimethylformamide|DMF]], 60&nbsp;°C, [[Azobisisobutyronitrile|AIBN]]

|-

| [[Vinyl Acetate]]

| 0.05

| 11.60 ^†

| [[Methanol]], 60&nbsp;°C,

|-

| [[N-Vinylpyrrolidone]]

| 0.13

| 0.66 ^†

| 60&nbsp;°C, [[Azobisisobutyronitrile|AIBN]]

|-

| [[2-hydroxyethyl methacrylate]]

| 0.86

| 0.90

| Water, 60&nbsp;°C, [[Azobisisobutyronitrile|AIBN]]

|-

| [[2-Hydroxypropyl methacrylate]]

| 6.30

| 0.04

| Water, 80&nbsp;°C, (NH₄)₂S₂O₈

|-

| [[N,N-Dimethylacrylamide]]

| 1.26

| 0.68 ^†

| Water, 30&nbsp;°C, K₂S₂O₈

|-

| [[N-Vinylformamide]]

| 0.32

| 0.39 ^†

| VA-044

|}

== 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.<ref>{{patent|EP|1611278|application|W. Brennich et al., Applicant: CHT R. Beitlich GmbG, filing date 24. January 2007}}</ref>

* Coating and adhesive: Its [[sulfonic acid]] group gives the monomers ionic character over a wide range of pH. Anionic charges from AMPS fixed on polymer particles enhance the chemical and [[Shear strength (soil)|shear stabilities]] of polymer emulsion and also reduce the amount of [[surfactants]] leaching out of paint film.<ref>H. Kim, G. P. Marks, and C. Piedrahita, "Superior latex stability and enhanced control of paint rheology using sodium 2-acrylamido-2-methylpropane sulfonate", 236th ACS National Meeting in Philadelphia, Polymeric Materials Science and Engineering Preprint 99, 795 (2008)</ref><ref>{{cite journal |last1=Yang |first1=Yu-Kun |last2=Li |first2=Hao |last3=Wang |first3=Feng |date=January 2003 |title=Studies on the water resistance of acrylic emulsion pressure-sensitive adhesives (PSAs) |url=http://www.tandfonline.com/doi/abs/10.1163/156856103322538651 |journal=Journal of Adhesion Science and Technology |language=en |volume=17 |issue=13 |pages=1741–1750 |doi=10.1163/156856103322538651 |s2cid=93181237 |issn=0169-4243}}</ref><ref>{{patent|EP|0973807| Inventor: R. Figge, H.-P. Weitzel, Applicant: Wacker-Chemie GmbH, registered at 20. September 2000}}</ref> It improves the thermal and mechanical properties of adhesives, and increases the adhesive strength of pressure-sensitive adhesive formulations.<ref>{{patent|US|4012560|Inventor: J.C. Baatz, A.E. Corey, Applicant: Monsanto Co., registered at 15. March 1977}} and WO 2007/057333, Inventor: A. Hashemzadeh, Applicant: Wacker Polymer Systems, registered at 24. Mai 2007</ref>

* Detergents: Enhances the washing performance of [[surfactant]]s by binding multivalent cations and reducing dirt attachment.<ref>{{patent|US|7928047|Inventor: M.-S. Cho, Applicant: LG Household & Health Care Ltd., registered at 19. April 2011}}</ref>

* Personal care: Strong polar and hydrophilic properties introduced to a high molecular weight AMPS homopolymer are exploited as a very efficient [[lubricant]] characteristic for skin care.<ref>{{patent|US|4128631|"Method of imparting lubricity to keratinous substrates and mucous membranes"}}</ref><ref name="Löffler">{{patent|EP1236464|Inventor: M. Löffler et al., Applicant: Clariant GmbH, registered at 4. September 2002 und EP 2 055 315, Inventor: R. von Eben-Worlée et al., Applicant: Worlée-Chemie, registered at 6. May 2009}}</ref>

* Medical [[hydrogel]]: High water-absorbing and swelling capacity when AMPS is introduced to a hydrogel are keys to medical applications. Hydrogel with AMPS 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.<ref>{{patent|US|4581821|"Method of preparing tape electrode"}}</ref><ref>{{patent|US|4593053|"Hydrophilic pressure sensitive biomedical adhesive composition"}}</ref><ref>{{patent|US|4768523|"Hydrogel adhesive"}}</ref> In addition, polymers derived from AMPS are used as the absorbing hydrogel and the [[tackifier]] component of wound dressings.<ref name="Löffler" /><ref>{{patent|US|4759354|"Wound dressing"}}</ref><ref>G. P. Marks, "A review of the benefits of polymers based on 2-acrylamido-2-methylpropane sulphonic acid, AMPS in medical applications: coatings, electrodes, wound care and dermal delivery systems", European Coatings Conference, Medical Coatings and Adhesives 2008</ref> Is used due to its high water absorption and retention capability as a monomer in superabsorbents e. g. for baby diapers.<ref>WO 2011/131526, Inventor: N. Herfert et al., Applicant: BASF SE, registered at 27. October 2011</ref>

* 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,<ref>Lubrizol, AMPS(R) Specialty Monomers, Oil Field Applications</ref> high temperature and high pressure are present, AMPS 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 AMPS-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.<ref>Z. Amjad and R. W. Zhul, "particle size and microscopic investigation of iron oxide foulants in the presence of dispersants", Association of Water technologies, Inc. 18th Annual Convention & Exposition, Charlotte, NC(2006)</ref><ref>{{cite journal |last=Amjad |first=Z. |date=2007-08-01 |title=Influence of Polymer Architecture on the Stabilization of Iron and Manganese Ions in Aqueous Systems |url=https://www.degruyter.com/document/doi/10.3139/113.100339/html |journal=Tenside Surfactants Detergents |language=en |volume=44 |issue=4 |pages=202–208 |doi=10.3139/113.100339 |s2cid=53546601 |issn=2195-8564}}</ref>

*Crop protection: increases in dissolved<ref>Patent US20110166309: Preparation containing at least one type of fungicidal conazole. Registered at 14. März 2011, registered at 7. July 2011, Applicant: BASF, Inventor: Sebastian Koltzenburg et al.</ref> and nanoparticulate<ref>EP 1 681 923, Inventor: S. Koltzenburg et al., Applicant: BASF AG, registered at 20. April 2011</ref> polymer formulations bioavailability of pesticides in aqueous-organic formulations.

*Membranes: It increases water flow, retention and fouling resistance of asymmetric [[ultrafiltration]] and [[microfiltration]] membranes<ref>{{patent|US|6183640|Inventor: I. Wang, Applicant: USF Filtration and Separations Group, Inc., registered at 6. February 2001}}</ref> and is being studied as an anionic component in [[polymer fuel cell membranes]].<ref>{{patent|US|2008/020255|Inventor: H. Hiraoka, T. Yamaguchi, Applicant: Toagosei Co., Ltd., registered at 24. Januar 2008}}</ref><ref>{{cite magazine |last1=Diao |first1=Hanbin |last2=Yan |first2=Feng |last3=Qiu |first3=Lihua |last4=Lu |first4=Jianmei |last5=Lu |first5=Xinhua |last6=Lin |first6=Bencai |last7=Li |first7=Qing |last8=Shang |first8=Songmin |last9=Liu |first9=Wenming |date=2010-08-10 |title=High Performance Cross-Linked Poly(2-acrylamido-2-methylpropanesulfonic acid)-Based Proton Exchange Membranes for Fuel Cells |url=https://pubs.acs.org/doi/10.1021/ma1010099 |magazine=Macromolecules |language=en |volume=43 |issue=15 |pages=6398–6405 |doi=10.1021/ma1010099 |issn=0024-9297}}</ref>

* Construction applications: [[Superplasticizer]]s with AMPS are used to reduce water in [[concrete]] formulations. Benefits of these additives include improved strength, improved workability, improved durability of cement mixtures.<ref>{{cite journal |last1=Liao |first1=Tung-Sheng |last2=Hwang |first2=Chao-Lung |last3=Ye |first3=Yi-Shian |last4=Hsu |first4=Kung-Chung |date=April 2006|title=Effects of a carboxylic acid/sulfonic acid copolymer on the material properties of cementitious materials |url=https://linkinghub.elsevier.com/retrieve/pii/S000888460500236X |journal=Cement and Concrete Research |language=en |volume=36 |issue=4 |pages=650–655 |doi=10.1016/j.cemconres.2005.10.005}}</ref> Redispersible polymer powder, when AMPS is introduced, in cement mixtures control air pore content and prevent [[Flocculation|agglomeration]] of powders during the spray-drying process from the powder manufacturing and storage.<ref>L.M. Saija and M.Uminski, "Water redispersible acrylic powders for the modification of hydraulic binder compositions" J. Appl. Polym .Sci. 71, 1781 (1999), {{doi|10.1002/(SICI)1097-4628(19990314)71:11<1781::AID-APP7>3.0.CO;2-2}}.</ref> Coating formulations with AMPS-containing polymers prevent calcium ions from being formed as [[Lime plaster|lime]] on concrete surface and improve the appearance and durability of coating.<ref>{{patent|US|6569970|"Preservation of a mineral molding."}}</ref>

==See also==

* [[PolyAMPS]]

* [[Hydrogel]]

== References ==

{{reflist}}

* Composition analysis of AMPS-vinyl amide copolymers. J.polym. materials 8(1991)287-289

* Synthesis and characterization of AMPS copolymers with vinylamides by Solution and thermal studies J.polym. materials 11(1994) 207-210.

* High Temperature Molecular relaxations in EMA-AMPS copolymers. recent advances in Polymer Science. Vol.-II 879-(1994)allied publishers.

* Thermoluminescence in probing molecular relaxations and degradation studies of MMA-AMPS copolymers. Bulletin of Electro Chemistry 9(2 & 3) feb. March 1993,pp.&nbsp;143–145

{{DEFAULTSORT:Acrylamido-2-Methylpropane Sulfonic Acid, 2-}}

[[Category:Monomers]]

[[Category:Polyelectrolytes]]

[[Category:Sulfonates]]

[[Category:Anionic surfactants]]

[[Category:Vinyl compounds]]