WordNet

a silvery soft waxy metallic element of the alkali metal group; occurs abundantly in natural compounds (especially in salt water); burns with a yellow flame and reacts violently in water; occurs in sea water and in the mineral halite (rock salt) (同)Na, atomic number 11
a polymer of styrene; a rigid transparent thermoplastic; "expanded polystyrene looks like a rigid white foam and is used as packing or insulation"
a salt of sulphonic acid

PrepTutorEJDIC

ソジウム,ナトリウム(金属元素;化学記号はNa)
ポリスチレン,スチロール樹脂(温遅調節装置の絶縁材などに用いる)

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/10/13 13:09:47」(JST)

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Polystyrene sulfonates are polymers derived from polystyrene but containing sulfonic acid or sulfonate functional groups. The linear polymer is white when very pure and is water-soluble. The crosslinked material (called a resin) does not dissolve in water and typically appears amber in color. These polymers are classified as polysalts and ionomers. They are widely used to remove ions from a solution in technical or medical applications.^[1]

Production and chemical structure

Polystyrene sulfonic acid has the idealized formula (CH₂CHC₆H₄SO₃H)_n. The material is prepared by sulfonation of polystyrene:

(CH₂CHC₆H₅)_n + n SO₃ → (CH₂CHC₆H₄SO₃H)_n

Several methods exist for this conversion, which can lead to varying degree of sulfonation. Usually the polystyrene is crosslinked, which keeps the polymer from dissolving. Since the sulfonic acid group (SO₃H) is strongly acidic, this polymer neutralizes bases. In this way, various salts of the polymer can be prepared, leading to sodium, calcium, and other salts:

(CH₂CHC₆H₄SO₃H)_n + n NaOH → (CH₂CHC₆H₄SO₃Na)_n + n H₂O

These ion-containing polymers are called ionomers.

Alternative sulfonation methods

Double substitutions of the phenyl rings are known to occur, even with conversions well below 100%. Crosslinking reactions are also found, where condensation of two sulfonic acid groups yields a sulfonyl crosslink. On the other hand, the use of milder conditions such as acetyl sulfate leads to incomplete sulfonation. Recently, the atom transfer radical polymerization (ATRP) of protected styrenesulfonates has been reported,^[2]^[3] leading to well defined linear polymers, as well as more complicated molecular architectures.^[4]

Applications

Polystyrene sulfonates are useful because of their ion exchange properties.^[1]

Water softening

Water softening is achieved by percolating hard water through a bed of sodium form of cross-linked polystyrene sulfonate. The hard ions such as calcium (Ca²⁺) and magnesium (Mg²⁺) adhere to the sulfonate groups, displacing sodium ions. The resulting solution of sodium ions is softened.

Idealized image of water softening process involving replacement of calcium ions in water with sodium ions donated by a cation exchange resin.

Medical applications

For medical applications, polystyrene sulfonate is usually supplied in the sodium and calcium form. Its use is indicated as potassium binders in acute and chronic kidney disease for patients suffering from hyperkalaemia (abnormal high blood serum potassium levels), which may, e.g., result in weakness or irregular heartbeat.^[5]^[6] Excess blood potassium also arises due to digoxin toxicity,^[7] although there is concern about possible side effects when it is mixed with sorbitol.^[8]

Micrograph showing sodium polystyrene sulfonate crystals (purple – at top of the image) in the biopsy of a colonic mass. H&E stain.

Polystyrene sulfonates are administered orally (with a meal) or rectally, by retention enema.^[9] In the large intestines, potassium derived from food is exchanged for sodium or calcium ions, respectively.^[10] Finally, the indigestible potassium polystryene sulfonate complex is excreted with the feces, preventing the absorption of potassium into the blood stream. Hence, the serum potassium level decreases.

Side-effects

Intestinal disturbances are common, including loss of appetite, nausea, vomiting, and constipation. In rare cases, it has been associated with colonic necrosis.^[11] Changes in electrolyte blood levels may occur such as hypermagnesemia, hypercalcemia, and hypokalemia.^[5]

Other uses

Sodium polystyrene sulfonate is used as a superplastifier in cement, as a dye improving agent for cotton, and as proton exchange membranes in fuel cell applications. In their acid form, the resin is used as a solid acid catalyst in organic synthesis.^[12]

References

^ ^a ^b François Dardel and Thomas V. Arden "Ion Exchangers" in Ullmann's Encyclopedia of Industrial Chemistry, 2008, Wiley-VCH, Weinheim. doi:10.1002/14356007.a14_393.pub2
^ Sikkema, FD; Comellas-Aragonès, M; Fokkink, RG; Verduin, BJ; Cornelissen, JJ; Nolte, RJ (2007). "Monodisperse polymer-virus hybrid nanoparticles". Organic & biomolecular chemistry 5 (1): 54–7. doi:10.1039/b613890j. PMID 17164905.
^ Lienkamp, Karen; Schnell, Ingo; Groehn, Franziska; Wegner, Gerhard (2006). "Polymerization of Styrene Sulfonate Ethyl Ester by ATRP: Synthesis and Characterization of Macromonomers for Suzuki Polycondensation". Macromolecular Chemistry and Physics 207 (22): 2066. doi:10.1002/macp.200600322.
^ Lienkamp, Karen; Ruthard, Christian; Lieser, GüNter; Berger, RüDiger; Groehn, Franziska; Wegner, Gerhard (2006). "Polymerization of Styrene Sulfonate Ethyl Ester and Styrene Sulfonate Dodecyl Ester by ATRP: Synthesis and Characterization of Polymer Brushes". Macromolecular Chemistry and Physics 207 (22): 2050. doi:10.1002/macp.200600321.
^ ^a ^b Sorbisterit – Summary of Product Characteristics; Retrieved: 27 November 2009.
^ MedlinePlus Encyclopedia High potassium level
^ Watson, M; Abbott, KC; Yuan, CM (2010). "Damned if you do, damned if you don't: potassium binding resins in hyperkalemia.". Clinical journal of the American Society of Nephrology : CJASN 5 (10): 1723–6. doi:10.2215/CJN.03700410. PMID 20798253.
^ Sterns RH, Rojas M, Bernstein P, Chennupati S (May 2010). "Ion-exchange resins for the treatment of hyperkalemia: are they safe and effective?". J. Am. Soc. Nephrol. 21 (5): 733–5. doi:10.1681/ASN.2010010079. PMID 20167700.
^ Medicines Complete: Martindale: The Complete Drug Reference, URL: http://www.medicinescomplete.com/mc/martindale/2009/5004-l.htm; Retrieved: 27 November 2009
^ Hyperkalemia~treatment at eMedicine
^ Rogers FB, Li SC (August 2001). "Acute colonic necrosis associated with sodium polystyrene sulfonate (Kayexalate) enemas in a critically ill patient: case report and review of the literature". J Trauma 51 (2): 395–7. doi:10.1097/00005373-200108000-00031. PMID 11493807.
^ Erik Gálvez, Pedro Romea, and Fèlix Urpí (2009). "Stereoselective Synthesis of anti α-Methyl-β-Methoxy Carboxylic Compounds". Org. Synth. 86: 81.

External links

Potassium and your CKD Diet - kidney.org
Information on Hyperkalaemia by Fresenius Medical Care - fmc-renalpharma.com

UpToDate Contents

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1. 成人における高カリウム血症の治療および予防 treatment and prevention of hyperkalemia in adults
2. Preanesthesia consultation for renal transplant recipients
3. 小児における高カリウム血症のマネージメント management of hyperkalemia in children
4. 透析患者における消化管疾患 gastrointestinal disease in dialysis patients
5. 小児における急性腎障害（急性腎不全）の予防およびマネージメント prevention and management of acute kidney injury acute renal failure in children

English Journal

A paper-based microbial fuel cell: instant battery for disposable diagnostic devices.

Fraiwan A, Mukherjee S, Sundermier S, Lee HS, Choi S.SourceDepartment of Electrical & Computer Engineering, State University of New York-Binghamton, Binghamton, NY 13902, USA.
Biosensors & bioelectronics.Biosens Bioelectron.2013 Nov 15;49:410-4. doi: 10.1016/j.bios.2013.06.001. Epub 2013 Jun 7.
We present a microfabricated paper-based microbial fuel cell (MFC) generating a maximum power of 5.5 μW/cm(2). The MFC features (1) a paper-based proton exchange membrane by infiltrating sulfonated sodium polystyrene sulfonate and (2) micro-fabricated paper chambers by patterning hydrophobic barrie
PMID 23807233

Sevelamer Crystals in the Gastrointestinal Tract (GIT): A New Entity Associated With Mucosal Injury.

Swanson BJ, Limketkai BN, Liu TC, Montgomery E, Nazari K, Park JY, Santangelo WC, Torbenson MS, Voltaggio L, Yearsley MM, Arnold CA.Source*Department of Pathology, the Ohio State University Wexner Medical Center, Columbus, OH Departments of †Medicine §Pathology ∥Pharmacy, Johns Hopkins School of Medicine, Baltimore, MD ‡Department of Pathology, Washington University, St Louis, MO ¶Department of Pathology, Children's Medical Center #Division of Gastroenterology, University of Texas Southwestern Medical Center, Dallas, TX **Department of Pathology, George Washington University, Washington, DC.
The American journal of surgical pathology.Am J Surg Pathol.2013 Nov;37(11):1686-93. doi: 10.1097/PAS.0b013e3182999d8d.
We report the first description of sevelamer crystals (Renagel and Renvela, Genzyme; phosphate-lowering agents) in the gastrointestinal tract. We prospectively collected cases with novel, histologically identical crystals from 4 major academic centers over a 1-year period and studied pertinent clini
PMID 24061514

Inflammatory Pseudotumor Containing Kayexalate Crystals: A Case Report and Review of the Literature.

Romano RC, Thirumala S, Cushman WH, Mounajjed T.AbstractKayexalate (sodium polystyrene sulfonate), a cation exchange resin often used to treat hyperkalemia, is known to produce gastrointestinal complications in a minority of patients. These complications range from mild gastrointestinal bleeding to perforation with acute abdomen. The typical histopathologic findings include mucosal ulceration, necrosis, and the presence of polygonal basophilic refractile crystals with a "fish scale" appearance. We present a unique case of Kayexalate crystals embedded in a perihepatic inflammatory pseudotumor, developing adjacent to a colostomy site in a 62-year-old woman following Kayexalate treatment. Microscopically, the lesion demonstrated a myofibroblastic proliferation rich in histiocytes and inflammation (lymphocytes, plasma cells, and eosinophils) as well as the presence of scattered typical Kayexalate crystals. This is the first report of extraintestinal Kayexalate identification in association with an inflammatory pseudotumor.
International journal of surgical pathology.Int J Surg Pathol.2013 Oct 31. [Epub ahead of print]
Kayexalate (sodium polystyrene sulfonate), a cation exchange resin often used to treat hyperkalemia, is known to produce gastrointestinal complications in a minority of patients. These complications range from mild gastrointestinal bleeding to perforation with acute abdomen. The typical histopatholo
PMID 24178951

Japanese Journal

メチルセルロース水溶液の曇点におよぼすスチレンスルホン酸ナトリウム単量体とその重合体添加による塩溶と塩析効果

繊維学会誌 71(10), 297-301, 2015
NAID 130005102595

Patterning of Cu thin films on layer-by-layer films of anionic polymer and TiO2 nanoparticles on plastic sheets

Transactions of the Materials Research Society of Japan 39(1), 67-70, 2014
NAID 130005004294

陽イオン交換樹脂を用いる放射性セシウムの除去

分析化学 = Japan analyst 62(6), 541-545, 2013-06-05
NAID 10031173790

Related Pictures

★リンクテーブル★

リンク元	「ポリスチレンスルホン酸」「ポリスチレンスルホン酸ナトリウム」「ケイキサレート」「calcium polystyrene sulfonate」「polystyrene sulfonate」
関連記事	「sulfonate」「polystyrene sulfonate」「polystyrene」

「ポリスチレンスルホン酸」

Polystyrene sulfonate
Systematic (IUPAC) name
	Poly(4-vinylbenzenesulfonic acid)
Clinical data
Trade names	Sodium salt: Kayexalate, Kionex, Resonium A, sodium polystyrene sulfonate; Calcium salt: Calcium Resonium, Sorbisterit, Resikali, Calcium Resonium, Sorbisterit, Resikali
AHFS/Drugs.com	monograph
MedlinePlus	a682108
Pregnancy; category	US: C (Risk not ruled out);
Legal status	℞ (Prescription only);
Routes of; administration	Oral, retention enema
Pharmacokinetic data
Bioavailability	None
Metabolism	None
Excretion	Faeces (100%)
Identifiers
CAS Registry Number	28210-41-5
ATC code	V03AE01
PubChem	CID: 75905
DrugBank	DB01344
Chemical data
Formula	[C8H8SO3]n
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