Polyacrylamide: Difference between revisions

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http://www.pipeline.com/~lenornst/DiscElectrophoresis.html | title = Disc Electrophoresis | archive-url = https://web.archive.org/web/20110926213111/http://www.pipeline.com/~lenornst/DiscElectrophoresis.html | archive-date = 26 September 2011 | work = Pipeline.com | access-date = 11 June 2012 }} citing: {{cite journal | vauthors = Ornstein L | title = Disc Electrophoresis. I. Background and Theory | journal = Annals of the New York Academy of Sciences | volume = 121 | issue = 2| pages = 321–49 | date = December 1964 | pmid = 14240533 | doi = 10.1111/j.1749-6632.1964.tb14207.x | bibcode = 1964NYASA.121..321O | s2cid = 28591995 }}</ref> and of Raymond and Weintraub<ref name=Davis/> independently published on the use of ] to separate charged ].<ref name=Davis>{{cite journal | vauthors = Raymond S, Weintraub L | title = Acrylamide gel as a supporting medium for zone electrophoresis | journal = Science | volume = 130 | issue = 3377 | pages = 711 | date = September 1959 | pmid = 14436634 | doi = 10.1126/science.130.3377.711 | s2cid = 7242716 | bibcode = 1959Sci...130..711R }} citing: {{cite journal | vauthors = Davis DR, Budd RE | title = Continuous electrophoresis; quantitative fractionation of serum proteins | journal = The Journal of Laboratory and Clinical Medicine | volume = 53 | issue = 6 | pages = 958–65 | date = June 1959 | pmid = 13665142 | doi = | url = }}</ref> The technique is widely accepted today, and remains a common ] in ] labs.

3116:{{cite journal | vauthors = Kay-Shoemake JL, Watwood ME, Lentz RD, Sojka RE | date = August 1998 | title = Polyacrylamide as an organic nitrogen source for soil microorganisms with potential effects on inorganic soil nitrogen in agricultural soil | journal = Soil Biology and Biochemistry | volume = 30 | issue = 8/9 | pages = 1045–1052 | doi = 10.1016/S0038-0717(97)00250-2 | bibcode = 1998SBiBi..30.1045K |url=https://naldc-legacy.nal.usda.gov/naldc/download.xhtml?id=30639&content=PDF}}</ref><ref>{{cite journal | vauthors = Gao J, Lin T, Wang W, Yu J, Yuan S, Wang S | year = 1999 | title = Accelerated chemical degradation of polyacrylamide | journal = Macromolecular Symposia | volume = 144 | pages = 179–185 | issn = 1022-1360 | doi = 10.1002/masy.19991440116 }}</ref><ref>{{cite journal | vauthors = Ver Vers LM | title = Determination of acrylamide monomer in polyacrylamide degradation studies by high-performance liquid chromatography | journal = Journal of Chromatographic Science | volume = 37 | issue = 12 | pages = 486–494 | date = December 1999 | pmid = 10615596 | doi = 10.1093/chromsci/37.12.486 | doi-access = free }}</ref> 2689:

with linear polyacrylamide as carrier | journal = Nucleic Acids Research | volume = 18 | issue = 2 | pages = 378 | date = January 1990 | pmid = 2326177 | pmc = 330293 | doi = 10.1093/nar/18.2.378 }}</ref><ref name=":0">{{cite journal | vauthors = Muterko A | title = Selective precipitation of RNA with linear polyacrylamide | journal = Nucleosides, Nucleotides & Nucleic Acids | volume = 41 | issue = 1 | pages = 61–76 | date = 2022-01-02 | pmid = 34809521 | doi = 10.1080/15257770.2021.2007397 | s2cid = 244490750 }}</ref> Many laboratory supply companies sell LPA for this use.<ref>{{cite web | url = http://www.biocompare.com/ProductDetails/349470/GenElute-LPA-from-Sigma-Aldrich.html | title = GenElute-LPA | author = Sigma-Aldrich | work = biocompare.com | archive-url = https://web.archive.org/web/20110718001006/http://www.biocompare.com/ProductDetails/349470/GenElute-LPA-from-Sigma-Aldrich.html | archive-date = 2011-07-18 }}</ref> In addition, under certain conditions, it can be used to selectively precipitate only RNA species from a mixture of nucleic acids.<ref name=":0" />

3094:{{cite journal | vauthors = Ahn JS, Castle L | title = Tests for the depolymerization of polyacrylamides as a potential source of acrylamide in heated foods | journal = Journal of Agricultural and Food Chemistry | volume = 51 | issue = 23 | pages = 6715–6718 | date = November 2003 | pmid = 14582965 | doi = 10.1021/jf0302308 }}</ref> The single claim that polyacrylamide reverts to acrylamide<ref>{{cite journal | vauthors = Smith EA, Prues SL, Oehme FW | title = Environmental degradation of polyacrylamides. II. Effects of environmental (outdoor) exposure | journal = Ecotoxicology and Environmental Safety | volume = 37 | issue = 1 | pages = 76–91 | date = June 1997 | pmid = 9212339 | doi = 10.1006/eesa.1997.1527 | url = http://www.mindfully.org/Plastic/Polymers/Polyacrylamides-Degradation1jun97.htm | access-date = 2007-11-02 | url-status = dead | archive-url = https://web.archive.org/web/20160420045005/http://www.mindfully.org/Plastic/Polymers/Polyacrylamides-Degradation1jun97.htm | archive-date = 2016-04-20 }}</ref> has been widely challenged.<ref> 2721:

journal = ACS Applied Materials & Interfaces | volume = 8 | issue = 34 | pages = 21893–21902 | date = August 2016 | pmid = 26816386 | doi = 10.1021/acsami.5b09344 }}</ref> This property makes polyacrylamide useful in the field of ], as a number of cells respond to mechanical stimuli.<ref>{{cite journal | vauthors = Pelham RJ, Wang Y | title = Cell locomotion and focal adhesions are regulated by substrate flexibility | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 94 | issue = 25 | pages = 13661–13665 | date = December 1997 | pmid = 9391082 | pmc = 28362 | doi = 10.1073/pnas.94.25.13661 | bibcode = 1997PNAS...9413661P | doi-access = free }}</ref>

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improve the economics of conventional water-flooding. In a separate application, ] benefits from drag reduction resulting from injection of these solutions. These applications use large volumes of polymer solutions at concentration of 30–3000 mg/L.<ref name=clean>{{cite journal |title=Polyacrylamide Degradation and Its Implications in Environmental Systems| vauthors = Xiong B, Loss RD, Shields D, Pawlik T, Hochreiter R, Zydney AL, Kumar M |journal= Clean Water|volume=1|year=2018| issue = 1 | page = 17 |doi=10.1038/s41545-018-0016-8|s2cid=135203788 |doi-access=free| bibcode = 2018npjCW...1...17X }}</ref>

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Assessment for the Challenge: 2-Propenamide (Acrylamide) |author1=Environment Canada|author2 = Health Canada |date=August 2009 |website = Environment and Climate Change Canada|publisher = Government of Canada |author1-link=Environment Canada }}</ref><ref name=NIOSHskin>{{Cite journal|url = https://www.cdc.gov/niosh/docs/2011-139/pdfs/2011-139.pdf|title = NIOSH skin notation (SK) profile: acrylamide .| vauthors = Dotson GS |date = April 2011 |journal = DHHS (NIOSH) Publication No. 2011-139 |publisher = National Institute for Occupational Safety and Health (NIOSH) }}</ref>

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https://web.archive.org/web/20171230230215/https://toxnet.nlm.nih.gov/cgi-bin/sis/search2/r?dbs+hsdb:@term+@rn+@rel+9003-05-8| archive-date = 30 December 2017 |title = Polyacrylamide|date = February 14, 2003|access-date = November 30, 2013|publisher = United States National Library of Medicine|at = Consumption Patterns|id = CASRN: 9003-05-8|website = Hazardous Substances Data Bank}}</ref> The next major application by weight is additives for ] processing and ]. About 30% of polyacrylamide is used in the oil and mineral industries.<ref name=Ull/>

1872:'''Polyacrylamide''' (abbreviated as PAM or pAAM) is a ] with the formula (-CH2CHCONH2-). It has a linear-chain structure. PAM is highly water-absorbent, forming a soft ] when hydrated. In 2008, an estimated 750,000,000 kg were produced, mainly for water treatment and the paper and mineral industries.<ref name=Ull>{{Ullmann |doi=10.1002/14356007.a21_143.pub2|title=Polyacrylamides and Poly(Acrylic Acids)|year=2015| vauthors = Herth G, Schornick G, Buchholz F |pages=1–16}}</ref> 2879:{{cite journal | vauthors = Woodrow JE, Seiber JN, Miller GC | title = Acrylamide release resulting from sunlight irradiation of aqueous polyacrylamide/iron mixtures | journal = Journal of Agricultural and Food Chemistry | volume = 56 | issue = 8 | pages = 2773–2779 | date = April 2008 | pmid = 18351736 | doi = 10.1021/jf703677v }}</ref> Considerable effort is made to scavenge traces of acrylamide from the polymer intended for use near food.<ref name=Ull/> 2568:

and a remaining carboxyl group. Thus, the degree of anionicity of the molecule increases. Thermal degradation of the vinyl backbone can occur through several possible radical mechanisms, including the autooxidation of small amounts of iron and reactions between oxygen and residual impurities from polymerization at elevated temperature. Mechanical degradation can also be an issue at the high shear rates experienced in the near-wellbore region.

1991:}}</ref> therefore it is recommended to handle it with caution. In the cross-linked form, the possibility of the monomer being present is reduced even further. It is highly water-absorbent, forming a soft ] when hydrated, used in such applications as ] and in manufacturing soft ]es. In the straight-chain form, it is also used as a ] and ] agent. More recently, it has been used as a subdermal filler for aesthetic facial surgery (see ]). 1881:'''Polyacrylamide''' (] '''poly(2-propenamide)''' or '''poly(1-carbamoylethylene)''') is a polymer (-CH2CHCONH2-) formed from ] subunits. It can be synthesized as a simple linear-chain structure or ]ed, typically using ]. Polyacrylamide is not toxic. However, unpolymerized acrylamide, which is a ], can be present in very small amounts in the polymerized acrylamide,<ref name="esd"> 3250:

degradation of polyacrylamide and the deamination product polyacrylate |journal=International Biodeterioration & Biodegradation |date=April 2019 |volume=139 |pages=24–33 |doi=10.1016/j.ibiod.2019.02.005|s2cid=92617790 |doi-access=free |bibcode=2019IBiBi.139...24N }}</ref>

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In dilute aqueous solution, such as is commonly used for ] applications, polyacrylamide polymers are susceptible to chemical, thermal, and mechanical degradation. Chemical degradation occurs when the labile amine moiety hydrolyzes at elevated temperature or pH, resulting in the evolution of ammonia

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It has also been advertised as a ] called ] by ] in the 1950s and today "MP", which is stated to be a "unique formulation of PAM (water-soluble polyacrylamide)". It is often used for horticultural and agricultural use under trade names such as Broadleaf P4, Swell-Gel and so on. The anionic form of

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The elastic modulus of polyacrylamide can be changed by varying the ratio of monomer to cross-linker during the fabrication of polyacrylamide gel.<ref>{{cite journal | vauthors = Denisin AK, Pruitt BL | title = Tuning the Range of Polyacrylamide Gel Stiffness for Mechanobiology Applications |

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The ionic forms of polyacrylamide has found an important role in the potable ]. Trivalent metal salts, like ] and ], are bridged by the long polymer chains of polyacrylamide. This results in significant enhancement of the ] rate. This allows ] plants to greatly improve the removal of total organic

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Polyacrylamide is a ]. It can be viewed as ] with amide substituents on alternating carbons. Unlike various ]s, polyacrylamide is not a ] because the amide groups are not in the polymer backbone. Owing to the presence of the amide (CONH2) groups, alternating carbon atoms in

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Considering the volume of polyacrylamide produced, these materials have been heavily scrutinized with regards to environmental and health impacts.<ref name="ecanada">{{cite web |url=http://www.ec.gc.ca/ese-ees/default.asp?lang=En&xml=FF4FCD6E-B330-7266-D1FD-B44C48A6BC9B |title=Screening

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Acrylamide has other uses in molecular biology laboratories, including the use of linear polyacrylamide (LPA) as a ], which aids in the precipitation of small amounts of nucleic acids (DNA and RNA).<ref>{{cite journal | vauthors = Gaillard C, Strauss F | title = Ethanol precipitation of DNA

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The ionic form of polyacrylamide has found an important role in the potable ]. Trivalent metal salts like ] and ] are bridged by the long polymer chains of polyacrylamide. This results in significant enhancement of the ] rate. This allows ] plants to greatly improve the removal of total organic

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Concerns have been raised that polyacrylamide used in agriculture may contaminate food with the nerve toxin ]. While polyacrylamide itself is relatively non-toxic, it is known that commercially available polyacrylamide contains minute residual amounts of acrylamide remaining from its production,

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Patent Number 4,797,145 filed in February 1986, by Garn A. Wallace and ] of Wallace Laboratories LLC, then published Jan. 10, 1989 - "Method of Agricultural Soil Improvement". As stated from the patent documents, ''Improvement in the physical properties of soils is achieved by the applicaton of

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In the oil and gas industry, polyacrylamide derivatives (especially co-polymers) have a substantial effect on production by enhanced oil recovery by viscosity enhancement. High viscosity aqueous solutions can be generated with low concentrations of polyacrylamide polymers, which are injected to

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Polyacrylamide is most commonly partially biodegraded by the action of ]s, producing ammonia and ]. Polyacrylates are hard to biodegrade, but some soil microbe cultures have been shown to do so in aerobic conditions.<ref>{{cite journal | vauthors = Nyyssölä A, Ahlgren J |title=Microbial

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The primary functions of polyacrylamide soil conditioners are to increase soil tilth, aeration, and porosity and reduce compaction, dustiness and water run-off. Typical applications are 10 mg/L, which is still expensive for many applications.<ref name=clean/> Secondary functions are to

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Polyacrylamide is also often used in molecular biology applications as a medium for electrophoresis of proteins and nucleic acids in a technique known as ]. PAGE was first used in a laboratory setting in the early 1950s. In 1959, the groups of Davis and Ornstein<ref>{{cite web | url =

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The primary functions of Polyacrylamide Soil Conditioners are to increase soil tilth, aeration, and porosity and reduce compaction, dustiness and water run-off. Secondary functions are to increase plant vigor, color, appearance, rooting depth and emergence of seeds while decreasing water

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Another common use of polyacrylamide and its derivatives is in subsurface applications such as Enhanced Oil Recovery. High viscosity aqueous solutions can be generated with low concentrations of polyacrylamide polymers, and these can be injected to improve the economics of conventional

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qwuecus mixtures of agricultural ] and ] to the soil. The combination of agricultural ] and ] results in greatly improving the physical properties of the soil while significantly reducing the quantity of agricultural polymers as compared to to methods of the prior art.''<ref>

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the backbone are ] (colloquially: chiral). For this reason, polyacrylamide exists in atactic, syndiotactic, and isotactic forms, although this aspect is rarely discussed. The polymerization is initiated with radicals and is assumed to be stereorandom.<ref name=Ull/>

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One of the largest uses for polyacrylamide is to ] solids in a liquid. This process applies to ], and processes like ] and screen printing. Polyacrylamide can be supplied in a powder or liquid form, with the liquid form being subcategorized as solution and emulsion

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cross-linked polyacrylamide is frequently used as a soil conditioner on farm land and ] for ], in order to protect the ] of nearby ] and streams.<ref>Wisconsin Department of Transportation. Madison, WI. January 2001. Report No. WI 06-98.</ref>

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Even though these products are often called 'polyacrylamide', many are actually ]s of ] and one or more other chemical species, such as an ] or a salt thereof. The main consequence of this is to give the 'modified' polymer a particular ] character.

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Partial hydrolysis occurs at elevated temperatures in aqueous media, converting some amide substituents to carboxylates. This hydrolysis thus makes the polymer particularly hydrophilic. The polymer produced from N,N-dimethylacrylamide resists

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Updating {{chembox}} (changes to watched fields - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref') per

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One of the largest uses for polyacrylamide is to ] or coagulate solids in a liquid. This process applies to ], and processes like ]. Most polyacrylamide is supplied in a liquid form. The liquid is subcategorized as solution and emulsion

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In one (much debated) study conducted in 1997 at ], the effect of environmental conditions on polyacrylamide were tested, and it was shown that degradation of polyacrylamide under certain conditions does in fact cause the release of

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In the 1970s and 1980s, the proportionately largest use of these polymers was in water treatment.<ref>{{Cite web|url = http://toxnet.nlm.nih.gov/cgi-bin/sis/search/r?dbs+hsdb:@term+@rn+@rel+9003-05-8 | archive-url =

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Polyacrylamide is of low toxicity but its precursor acrylamide is a ] and ].<ref name=Ull/> Thus, concerns naturally center on the possibility that polyacrylamide is contaminated with ].<ref name=NIOSHskin

86: 3224:}}</ref> California requires (current as of 2010) products containing acrylamide as an ingredient to be labeled with a statement that it is "a chemical known to the State of California to cause cancer." 2109:

Linear polyacrylamide is a water-soluble polymer. Other polar solvents include ] and various alcohols. ]ing can be introduced using ]. Some crosslinked materials are swellable but not soluble, i.e., they are

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Even though these products are often called 'polyacrylamide', many are actually ]s of ] and one or more other species, such as an ] or a salt thereof. These copolymers have modified wetting and swellability.

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The polymer is also used to make Gro-Beast toys, which expand when placed in water, such as the ]. Similarly, the absorbent properties of one of its copolymers can be utilized as an additive in body-powder.

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The polymer is also used to make Gro-Beast toys, which expand when placed in water, as the ]. Similarly, the absorbent properties of one of its copolymers can be utilized as an additive in body-powder.

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increase plant vigor, color, appearance, rooting depth, and emergence of seeds while decreasing water requirements, diseases, erosion and maintenance expenses. FC 2712 is used for this purpose.

11: 43: 57: 208: 1925:| title = Quantitation of Acrylamide (and Polyacrylamide): Critical review of methods for trace determination/formulation analysis & Future-research recommendations 100: 2591:

However, cross-linked variants of polyacrylamide have shown greater resistance to all of these methods of degradation, and have proved much more stable.

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Polyacrylamide is often used in molecular biology applications as a medium for electrophoresis of proteins and nucleic acids in a technique known as ].

202: 3436:| title = Polyacrylamide as an organic nitrogen source for soil microorganisms with potential effects on inorganic soil nitrogen in agricultural soil 3392:}}</ref> '''However''', the experimental design of this study, as well as its results and their interpretation have been questioned,<ref> 116: 243: 161: 3667:| title = Determination of acrylamide monomer in polyacrylamide degradation studies by high-performance liquid chromatography 232: 24: 250: 216: 157: 267:

Changed "gel electrophoresis" link to more specific "polyacrylamide gel electrophoresis" link.

3147:| title = Tests for the Depolymerization of Polyacrylamides as a Potential Source of Acrylamide in Heated Foods 220: 179: 87: 239: 3623:}}</ref> and in a study conducted in 1999 by the ], the results could not be replicated.<ref> 3304:| title = Environmental degradation of polyacrylamides. II. Effects of environmental (outdoor) exposure. 2921:| title = Acrylamide Release Resulting from Sunlight Irradiation of Aqueous Polyacrylamide/Iron Mixtures 168: 58: 44: 2467:| url = http://www.wikipatents.com/US-Patent-4797145/method-of-agricultural-soil-improvement 3063:

Additionally, there are concerns that polyacrylamide may de-polymerise to form acrylamide.

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Additionally, there are concerns that polyacrylamide may de-polymerise to form acrylamide.

101: 765:| Formula = (C3H5NO)n 758:| Formula = (C3H5NO)n 8: 3359:| url = http://www.mindfully.org/Plastic/Polymers/Polyacrylamides-Degradation1jun97.htm 175: 3050:

was treated similarly as food during cooking. It was shown that these conditions do

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It has been used in Botox as a ] for aesthetic facial surgery (see ]).

112: 111: 274:(178 intermediate revisions by more than 100 users not shown) 3557:| title = Accelerated chemical degradation of polyacrylamide 3414:| author = Kay-Shoemake JL, Watwood ME, Lentz RD, Sojka RE. 3535:| author = Gao JP, Lin T, Wang W, Yu JG, Yuan SJ, Wang SM. 489:| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} 2332:

requirements, diseases, erosion and maintenance expenses.

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Copolymers of ] include those derived from acrylic acid.

1958:| url = http://www.epa.gov/esd/pdf/qoa%28Jan-2010%29.pdf 139: 2792:It was also used in the synthesis of the first ]. 2412:| title = Method of agricultural soil improvement 452:poly(2-propenamide), poly(1-carbamoylethylene) 2899:| author = Woodrow JE, Seiber JN, Miller GC. 2390:| author = Garn Wallace & Arthur Wallace 263: 3083:not de-polymerise significantly.<ref> 217:Latest revision as of 06:33, 23 August 2024 3282:| author = Smith EA, Prues SL, Oehme FW. 3056:de-polymerise significantly.<ref> 2086:===Copolymers and modified polymers=== 667:| KEGG_Ref = {{keggcite|correct|kegg}} 660:| KEGG_Ref = {{keggcite|correct|kegg}} 3502:| doi = 10.1016/S0038-0717(97)00250-2 2866:usually less than 0.05% ].<ref> 562:| UNII1_Ref = {{fdacite|correct|FDA}} 551:| CASNo_Ref = {{cascite|correct|CAS}} 77: 34: 2656:===Molecular biology laboratories=== 158:Revision as of 12:07, 24 August 2011 148: 131: 1055:|Section4={{Chembox Thermochemistry 544:CASNo_Ref = {{cascite|correct|CAS}} 273: 262: 231: 214: 207: 198: 167: 155: 9: 120: 4177: 1903:| author = Daughlon, Christian G. 747:| Section2 = {{Chembox Properties 95: 81: 52: 38: 2016:== Physicochemical properties == 1144:|Section5={{Chembox Pharmacology 378:| ImageFile = Polyacrylamide.svg 368:| ImageFile = Polyacrylamide.svg 478:|Section1={{Chembox Identifiers 3370:| doi = 10.1006/eesa.1997.1527 2558:{{main|Enhanced oil recovery}} 716:|Section2={{Chembox Properties 1: 4160: 4149: 4138: 4127: 4116: 4105: 4094: 4083: 4072: 4061: 4052: 4043: 4016: 4009: 3954: 3943: 3934: 3923: 3914: 3899: 3885: 3814: 3807: 3792: 3785: 3762: 3751: 3740: 3729: 3718: 3707: 3696: 3685: 3674: 3663: 3652: 3641: 3630: 3619: 3608: 3597: 3586: 3575: 3564: 3553: 3542: 3531: 3520: 3509: 3498: 3487: 3476: 3465: 3454: 3443: 3432: 3421: 3410: 3399: 3388: 3377: 3366: 3355: 3344: 3333: 3322: 3311: 3300: 3289: 3278: 3267: 3255: 3245: 3220: 3209: 3198: 3187: 3176: 3165: 3154: 3143: 3132: 3121: 3112: 3099: 3090: 3059: 3028: 3005: 2994: 2983: 2972: 2961: 2950: 2939: 2928: 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326: 313: 302: 3125:| author = Ahn JS, Castle L. 2536:=== Fossil fuel industry === 14:Browse history interactively 7: 1729:|Section8={{Chembox Related 1410:|Section7={{Chembox Hazards 584:| UNII1_Comment = (1500 MW) 4182: 2025:==Uses of polyacrylamide== 4167: 4156: 4145: 4134: 4123: 4112: 4101: 4090: 4079: 4068: 4057: 4041: 3961: 3950: 3939: 3930: 3912: 3769: 3758: 3747: 3736: 3725: 3714: 3703: 3692: 3681: 3670: 3659: 3648: 3637: 3626: 3615: 3604: 3593: 3582: 3571: 3560: 3549: 3538: 3527: 3516: 3513:}}</ref><ref> 3505: 3494: 3483: 3472: 3461: 3450: 3439: 3428: 3417: 3406: 3395: 3384: 3373: 3362: 3351: 3340: 3329: 3318: 3307: 3296: 3285: 3274: 3263: 3243: 3227: 3216: 3205: 3202:| doi = 10.1021/jf0302308 3194: 3183: 3172: 3161: 3150: 3139: 3128: 3110: 3106: 3088: 3012: 3001: 2990: 2987:| doi = 10.1021/jf703677v 2979: 2968: 2957: 2946: 2935: 2924: 2913: 2902: 2891: 2873: 2869: 2849: 2825: 2820:==Environmental effects== 2813:==Environmental effects== 2786: 2777: 2766: 2757: 2746: 2735: 2726: 2714: 2703: 2694: 2682: 2673: 2661: 2650: 2641: 2629: 2624:{{main|soil conditioner}} 2618: 2607: 2598: 2594: 2575: 2571: 2552: 2548: 2530: 2514: 2503: 2492: 2481: 2470: 2459: 2448: 2437: 2426: 2415: 2404: 2393: 2382: 2371: 2351: 2335: 2316: 2292: 2252: 2233: 2217: 2198: 2182: 2163: 2147: 2127: 2103: 2099: 2080: 2064: 2052: 2032: 2028: 2010: 1994: 1983: 1972: 1969:| accessdate = 2010-06-30 1961: 1950: 1939: 1928: 1917: 1906: 1895: 1884: 1866: 1457: 1446: 1184: 1181: 1048:{{Chembox Thermochemistry 925: 922: 789: 786: 750: 739: 728: 710: 706: 688: 651: 648: 612: 578: 567: 556: 494: 483: 281: 278: 213: 154: 3136:| date = 5 November 2003 3046:in 2003 at the ] in ], ] 251:Extended confirmed users 3868:* ], a similar material 3861:* ], a similar material 3645:| author = Ver Vers LM. 3054:cause polyacrylamide to 2613:===Soil conditioning=== 359:| Name = Polyacrylamide 352:| Name = Polyacrylamide 203:Chem/Drugbox validation 153: 3656:| date = December 1999 3260:acrylamide.<ref> 2709:=== Mechanobiology === 2401:| date = Jan. 10, 1989 1137:{{Chembox Pharmacology 736:| ATC_Supplemental =}} 2910:| date = 2008 Apr 23; 1914:| date = 23 June 1988 500:| ChemSpiderID = none 471:{{Chembox Identifiers 414:| IUPACName = poly(2- 403:| IUPACName = poly(2- 370:|thumb|Polyacrylamide 3425:| date = August 1998 573:| UNII1 = 5D6TC4BRWV 109: 66: 3480:| pages = 1045–1052 2965:| pages = 2773–2779 1947:| publisher = The ] 1807:OtherFunction_label 1306:{{Chembox Explosive 1119:| HeatCapacity = }} 1112:| HeatCapacity = }} 975:{{Chembox Structure 725:| ATCCode_suffix = 703:| ATCCode_prefix = 532:| CASNo = 9003-05-8 525:| CASNo = 9003-05-8 434:| SystematicName = 427:| SystematicName = 69: 26: 3601:| issn = 1022-1360 3293:| date = June 1997 1238:Pregnancy_category 998:| CrystalStruct = 991:| CrystalStruct = 516:| Abbreviations = 509:| Abbreviations = 340:| verifiedrevid = 330:| verifiedrevid = 234:Alan U. Kennington 229: 165: 74: 31: 4170: 3711:| pages = 486–494 3590:| pages = 179–185 3079:, polyacrylamide 3048:, polyacrylamide 1761:| OtherCations = 1754:| OtherCations = 1722:{{Chembox Related 1403:{{Chembox Hazards 1345:| FrictionSens = 1338:| FrictionSens = 1014:| Coordination = 1007:| Coordination = 917:| SolubleOther = 910:| SolubleOther = 394:| ImageSize = 150 387:| ImageSize = 150 215: 156: 97: 83: 70: 54: 40: 27: 4173: 2856:/><ref> 2741:===Niche uses=== 2274:Soil Conditioner 2096:waterflooding. 1745:| OtherAnions = 1738:| OtherAnions = 1672:| ExploLimits = 1665:| ExploLimits = 1472:| MainHazards = 1465:| MainHazards = 1160:| AdminRoutes = 1153:| AdminRoutes = 609:| EINECSCASNO = 268: 265: 257: 247: 228: 223: 205: 193: 183: 164: 145: 144: 142: 137: 135: 127: 124: 113: 98: 84: 73: 55: 41: 30: 17: 15: 4181: 4180: 4176: 4175: 4174: 4172: 4171: 4165: 4154: 4143: 4132: 4121: 4110: 4099: 4088: 4077: 4066: 4055: 4048: 4037: 4030: 4021: 4014: 4005: 3998: 3989: 3982: 3973: 3968: 3959: 3948: 3937: 3928: 3919: 3908: 3906: 3897: 3895: 3892: 3881: 3876: 3869: 3862: 3853: 3846: 3837: 3830: 3821: 3820: 3812: 3803: 3801: 3798: 3790: 3781: 3776: 3767: 3756: 3745: 3734: 3723: 3712: 3701: 3690: 3679: 3668: 3657: 3646: 3635: 3624: 3613: 3602: 3591: 3580: 3569: 3558: 3547: 3536: 3525: 3514: 3503: 3492: 3481: 3470: 3459: 3448: 3437: 3426: 3415: 3404: 3393: 3382: 3371: 3360: 3349: 3348:| pages = 76–91 3338: 3327: 3316: 3305: 3294: 3283: 3272: 3261: 3251: 3239: 3234: 3225: 3214: 3203: 3192: 3181: 3170: 3159: 3148: 3137: 3126: 3117: 3104: 3095: 3084: 3082: 3078: 3075: 3072: 3069: 3066: 3057: 3055: 3051: 3047: 3044: 3041: 3038: 3035: 3024: 3019: 3010: 2999: 2988: 2977: 2966: 2955: 2944: 2933: 2922: 2911: 2900: 2889: 2880: 2867: 2857: 2845: 2840: 2833: 2821: 2814: 2805: 2800: 2793: 2782: 2773: 2762: 2753: 2742: 2731: 2722: 2710: 2699: 2690: 2678: 2669: 2657: 2646: 2637: 2625: 2614: 2603: 2592: 2583: 2569: 2559: 2546: 2545:== Stability == 2537: 2526: 2521: 2512: 2501: 2490: 2479: 2468: 2457: 2446: 2435: 2424: 2413: 2402: 2391: 2380: 2369: 2359: 2347: 2342: 2333: 2323: 2312: 2307: 2300: 2288: 2286: 2277: 2275: 2264: 2259: 2250: 2241: 2229: 2224: 2215: 2205: 2194: 2189: 2180: 2170: 2159: 2154: 2145: 2135: 2123: 2118: 2111: 2097: 2087: 2076: 2071: 2062: 2050: 2040: 2026: 2017: 2006: 2001: 1992: 1981: 1970: 1959: 1948: 1937: 1926: 1915: 1904: 1893: 1882: 1873: 1862: 1857: 1850: 1843: 1834: 1832: 1823: 1821: 1810: 1808: 1799: 1797: 1786: 1784: 1775: 1773: 1762: 1755: 1746: 1739: 1730: 1723: 1721: 1718: 1715: 1705: 1698: 1689: 1682: 1673: 1666: 1657: 1655: 1646: 1644: 1633: 1626: 1617: 1615: 1606: 1604: 1593: 1591: 1582: 1580: 1569: 1567: 1558: 1556: 1545: 1543: 1534: 1532: 1521: 1514: 1505: 1498: 1489: 1482: 1473: 1466: 1455: 1444: 1435: 1433: 1424: 1422: 1411: 1404: 1402: 1399: 1396: 1386: 1385:| REFactor = }} 1379: 1378:| REFactor = }} 1370: 1368: 1359: 1357: 1346: 1339: 1330: 1323: 1314: 1307: 1305: 1302: 1299: 1289: 1287: 1278: 1276: 1265: 1263: 1254: 1252: 1241: 1239: 1230: 1228: 1217: 1210: 1201: 1194: 1177: 1170: 1161: 1154: 1145: 1138: 1136: 1133: 1130: 1120: 1113: 1104: 1097: 1088: 1081: 1072: 1065: 1056: 1049: 1047: 1044: 1041: 1031: 1030:| MolShape = }} 1024: 1023:| MolShape = }} 1015: 1008: 999: 992: 983: 976: 974: 971: 968: 958: 951: 942: 935: 918: 911: 902: 901:| Solubility = 895: 894:| Solubility = 886: 884: 883:BoilingPt_notes 875: 873: 862: 855: 846: 844: 843:MeltingPt_notes 835: 833: 822: 815: 806: 799: 782: 775: 766: 759: 748: 737: 726: 717: 704: 695: 684: 677: 668: 661: 644: 637: 628: 621: 610: 601: 594: 585: 574: 563: 552: 545: 543: 533: 526: 517: 510: 501: 490: 479: 472: 470: 467: 464: 454: 453: 444: 443:| OtherNames = 435: 428: 419: 417: 408: 406: 395: 388: 379: 372: 371: 360: 353: 344: 343: 334: 333: 322: 320: 311: 309: 298: 291: 269: 266: 261: 260: 259: 255: 253: 237: 235: 230: 224: 219: 211: 209:← Previous edit 206: 199: 197: 196: 195: 191: 189: 173: 171: 166: 160: 152: 151: 150: 149: 147: 146: 140: 138: 133: 130: 128: 125: 123:Content deleted 122: 119: 117:← Previous edit 114: 110: 108: 107: 106: 105: 104: 103: 102: 94: 91: 90: 89: 88: 80: 71: 67: 65: 64: 63: 62: 61: 60: 59: 51: 48: 47: 46: 45: 37: 28: 22: 21: 20: 13: 5: 4179: 4169: 4168: 4166: 4163: 4161: 4158: 4157: 4155: 4152: 4150: 4147: 4146: 4144: 4141: 4139: 4136: 4135: 4133: 4130: 4128: 4125: 4124: 4122: 4119: 4117: 4114: 4113: 4111: 4108: 4106: 4103: 4102: 4100: 4097: 4095: 4092: 4091: 4089: 4086: 4084: 4081: 4080: 4078: 4075: 4073: 4070: 4069: 4067: 4064: 4062: 4059: 4058: 4056: 4053: 4050: 4049: 4046: 4044: 4042: 4039: 4038: 4035: 4033: 4031: 4028: 4026: 4023: 4022: 4019: 4017: 4015: 4012: 4010: 4007: 4006: 4003: 4001: 3999: 3996: 3994: 3991: 3990: 3987: 3985: 3983: 3980: 3978: 3975: 3974: 3971: 3969: 3966: 3963: 3962: 3960: 3957: 3955: 3952: 3951: 3949: 3947:==References== 3946: 3944: 3941: 3940: 3938: 3935: 3932: 3931: 3929: 3926: 3924: 3921: 3920: 3917: 3915: 3913: 3910: 3909: 3904: 3902: 3900: 3898: 3893: 3890: 3888: 3886: 3883: 3882: 3879: 3877: 3874: 3871: 3870: 3867: 3865: 3863: 3860: 3858: 3855: 3854: 3851: 3849: 3847: 3844: 3842: 3839: 3838: 3835: 3833: 3831: 3828: 3826: 3823: 3822: 3819: 3817: 3815: 3813: 3810: 3808: 3805: 3804: 3800: 3797: 3795: 3793: 3791: 3788: 3786: 3783: 3782: 3779: 3777: 3774: 3771: 3770: 3768: 3766:}}</ref> 3765: 3763: 3760: 3759: 3757: 3754: 3752: 3749: 3748: 3746: 3743: 3741: 3738: 3737: 3735: 3732: 3730: 3727: 3726: 3724: 3721: 3719: 3716: 3715: 3713: 3710: 3708: 3705: 3704: 3702: 3699: 3697: 3694: 3693: 3691: 3688: 3686: 3683: 3682: 3680: 3677: 3675: 3672: 3671: 3669: 3666: 3664: 3661: 3660: 3658: 3655: 3653: 3650: 3649: 3647: 3644: 3642: 3639: 3638: 3636: 3634:{{cite journal 3633: 3631: 3628: 3627: 3625: 3622: 3620: 3617: 3616: 3614: 3611: 3609: 3606: 3605: 3603: 3600: 3598: 3595: 3594: 3592: 3589: 3587: 3584: 3583: 3581: 3579:| volume = 144 3578: 3576: 3573: 3572: 3570: 3567: 3565: 3562: 3561: 3559: 3556: 3554: 3551: 3550: 3548: 3545: 3543: 3540: 3539: 3537: 3534: 3532: 3529: 3528: 3526: 3524:{{cite journal 3523: 3521: 3518: 3517: 3515: 3512: 3510: 3507: 3506: 3504: 3501: 3499: 3496: 3495: 3493: 3490: 3488: 3485: 3484: 3482: 3479: 3477: 3474: 3473: 3471: 3468: 3466: 3463: 3462: 3460: 3457: 3455: 3452: 3451: 3449: 3446: 3444: 3441: 3440: 3438: 3435: 3433: 3430: 3429: 3427: 3424: 3422: 3419: 3418: 3416: 3413: 3411: 3408: 3407: 3405: 3403:{{cite journal 3402: 3400: 3397: 3396: 3394: 3391: 3389: 3386: 3385: 3383: 3380: 3378: 3375: 3374: 3372: 3369: 3367: 3364: 3363: 3361: 3358: 3356: 3353: 3352: 3350: 3347: 3345: 3342: 3341: 3339: 3336: 3334: 3331: 3330: 3328: 3325: 3323: 3320: 3319: 3317: 3314: 3312: 3309: 3308: 3306: 3303: 3301: 3298: 3297: 3295: 3292: 3290: 3287: 3286: 3284: 3281: 3279: 3276: 3275: 3273: 3271:{{cite journal 3270: 3268: 3265: 3264: 3262: 3258: 3256: 3253: 3252: 3248: 3246: 3244: 3241: 3240: 3237: 3235: 3232: 3229: 3228: 3226: 3223: 3221: 3218: 3217: 3215: 3212: 3210: 3207: 3206: 3204: 3201: 3199: 3196: 3195: 3193: 3190: 3188: 3185: 3184: 3182: 3179: 3177: 3174: 3173: 3171: 3168: 3166: 3163: 3162: 3160: 3157: 3155: 3152: 3151: 3149: 3146: 3144: 3141: 3140: 3138: 3135: 3133: 3130: 3129: 3127: 3124: 3122: 3119: 3118: 3115: 3113: 3111: 3108: 3107: 3105: 3103:{{cite journal 3102: 3100: 3097: 3096: 3093: 3091: 3089: 3086: 3085: 3080: 3076: 3073: 3070: 3067: 3064: 3062: 3060: 3058: 3053: 3049: 3045: 3042: 3039: 3036: 3033: 3031: 3029: 3026: 3025: 3022: 3020: 3017: 3014: 3013: 3011: 3009:}}</ref> 3008: 3006: 3003: 3002: 3000: 2997: 2995: 2992: 2991: 2989: 2986: 2984: 2981: 2980: 2978: 2975: 2973: 2970: 2969: 2967: 2964: 2962: 2959: 2958: 2956: 2953: 2951: 2948: 2947: 2945: 2942: 2940: 2937: 2936: 2934: 2931: 2929: 2926: 2925: 2923: 2920: 2918: 2915: 2914: 2912: 2909: 2907: 2904: 2903: 2901: 2898: 2896: 2893: 2892: 2890: 2888:{{cite journal 2887: 2885: 2882: 2881: 2878: 2876: 2874: 2871: 2870: 2868: 2864: 2862: 2859: 2858: 2854: 2852: 2850: 2847: 2846: 2843: 2841: 2838: 2835: 2834: 2830: 2828: 2826: 2823: 2822: 2819: 2817: 2815: 2812: 2810: 2807: 2806: 2803: 2801: 2798: 2795: 2794: 2791: 2789: 2787: 2784: 2783: 2780: 2778: 2775: 2774: 2771: 2769: 2767: 2764: 2763: 2760: 2758: 2755: 2754: 2751: 2749: 2747: 2744: 2743: 2740: 2738: 2736: 2733: 2732: 2729: 2727: 2724: 2723: 2719: 2717: 2715: 2712: 2711: 2708: 2706: 2704: 2701: 2700: 2697: 2695: 2692: 2691: 2687: 2685: 2683: 2680: 2679: 2676: 2674: 2671: 2670: 2666: 2664: 2662: 2659: 2658: 2655: 2653: 2651: 2648: 2647: 2644: 2642: 2639: 2638: 2634: 2632: 2630: 2627: 2626: 2623: 2621: 2619: 2616: 2615: 2612: 2610: 2608: 2605: 2604: 2601: 2599: 2596: 2595: 2593: 2590: 2588: 2585: 2584: 2580: 2578: 2576: 2573: 2572: 2570: 2566: 2564: 2561: 2560: 2557: 2555: 2553: 2550: 2549: 2547: 2544: 2542: 2539: 2538: 2535: 2533: 2531: 2528: 2527: 2524: 2522: 2519: 2516: 2515: 2513: 2511:}}</ref> 2510: 2508: 2505: 2504: 2502: 2499: 2497: 2494: 2493: 2491: 2488: 2486: 2483: 2482: 2480: 2477: 2475: 2472: 2471: 2469: 2466: 2464: 2461: 2460: 2458: 2455: 2453: 2450: 2449: 2447: 2444: 2442: 2439: 2438: 2436: 2433: 2431: 2428: 2427: 2425: 2422: 2420: 2417: 2416: 2414: 2411: 2409: 2406: 2405: 2403: 2400: 2398: 2395: 2394: 2392: 2389: 2387: 2384: 2383: 2381: 2379:{{cite journal 2378: 2376: 2373: 2372: 2370: 2366: 2364: 2361: 2360: 2356: 2354: 2352: 2349: 2348: 2345: 2343: 2340: 2337: 2336: 2334: 2330: 2328: 2325: 2324: 2321: 2319: 2317: 2314: 2313: 2310: 2308: 2305: 2302: 2301: 2297: 2295: 2293: 2290: 2289: 2284: 2282: 2280: 2278: 2273: 2271: 2269: 2266: 2265: 2262: 2260: 2257: 2254: 2253: 2251: 2248: 2246: 2243: 2242: 2238: 2236: 2234: 2231: 2230: 2227: 2225: 2222: 2219: 2218: 2216: 2212: 2210: 2207: 2206: 2203: 2201: 2199: 2196: 2195: 2192: 2190: 2187: 2184: 2183: 2181: 2177: 2175: 2172: 2171: 2168: 2166: 2164: 2161: 2160: 2157: 2155: 2152: 2149: 2148: 2146: 2142: 2140: 2137: 2136: 2132: 2130: 2128: 2125: 2124: 2121: 2119: 2116: 2113: 2112: 2108: 2106: 2104: 2101: 2100: 2098: 2094: 2092: 2089: 2088: 2085: 2083: 2081: 2078: 2077: 2074: 2072: 2069: 2066: 2065: 2063: 2059: 2057: 2054: 2053: 2051: 2047: 2045: 2042: 2041: 2037: 2035: 2033: 2030: 2029: 2027: 2024: 2022: 2019: 2018: 2015: 2013: 2011: 2008: 2007: 2004: 2002: 1999: 1996: 1995: 1993: 1990: 1988: 1985: 1984: 1982: 1980:| format = PDF 1979: 1977: 1974: 1973: 1971: 1968: 1966: 1963: 1962: 1960: 1957: 1955: 1952: 1951: 1949: 1946: 1944: 1941: 1940: 1938: 1935: 1933: 1930: 1929: 1927: 1924: 1922: 1919: 1918: 1916: 1913: 1911: 1908: 1907: 1905: 1902: 1900: 1897: 1896: 1894: 1891: 1889: 1886: 1885: 1883: 1880: 1878: 1875: 1874: 1871: 1869: 1867: 1864: 1863: 1860: 1858: 1855: 1852: 1851: 1848: 1846: 1844: 1841: 1839: 1836: 1835: 1831:OtherCompounds 1830: 1828: 1826: 1824: 1819: 1817: 1815: 1812: 1811: 1806: 1804: 1802: 1800: 1795: 1793: 1791: 1788: 1787: 1782: 1780: 1778: 1776: 1771: 1769: 1767: 1764: 1763: 1760: 1758: 1756: 1753: 1751: 1748: 1747: 1744: 1742: 1740: 1737: 1735: 1732: 1731: 1728: 1726: 1724: 1720: 1717: 1714: 1712: 1710: 1707: 1706: 1703: 1701: 1699: 1696: 1694: 1691: 1690: 1687: 1685: 1683: 1680: 1678: 1675: 1674: 1671: 1669: 1667: 1664: 1662: 1659: 1658: 1654:AutoignitionPt 1653: 1651: 1649: 1647: 1642: 1640: 1638: 1635: 1634: 1631: 1629: 1627: 1624: 1622: 1619: 1618: 1613: 1611: 1609: 1607: 1602: 1600: 1598: 1595: 1594: 1589: 1587: 1585: 1583: 1578: 1576: 1574: 1571: 1570: 1565: 1563: 1561: 1559: 1554: 1552: 1550: 1547: 1546: 1541: 1539: 1537: 1535: 1530: 1528: 1526: 1523: 1522: 1519: 1517: 1515: 1512: 1510: 1507: 1506: 1503: 1501: 1499: 1496: 1494: 1491: 1490: 1487: 1485: 1483: 1480: 1478: 1475: 1474: 1471: 1469: 1467: 1464: 1462: 1459: 1458: 1456: 1453: 1451: 1448: 1447: 1445: 1442: 1440: 1437: 1436: 1431: 1429: 1427: 1425: 1420: 1418: 1416: 1413: 1412: 1409: 1407: 1405: 1401: 1398: 1395: 1393: 1391: 1388: 1387: 1384: 1382: 1380: 1377: 1375: 1372: 1371: 1366: 1364: 1362: 1360: 1355: 1353: 1351: 1348: 1347: 1344: 1342: 1340: 1337: 1335: 1332: 1331: 1329:| ShockSens = 1328: 1326: 1324: 1322:| ShockSens = 1321: 1319: 1316: 1315: 1312: 1310: 1308: 1304: 1301: 1298: 1296: 1294: 1291: 1290: 1285: 1283: 1281: 1279: 1274: 1272: 1270: 1267: 1266: 1261: 1259: 1257: 1255: 1250: 1248: 1246: 1243: 1242: 1237: 1235: 1233: 1231: 1226: 1224: 1222: 1219: 1218: 1215: 1213: 1211: 1208: 1206: 1203: 1202: 1199: 1197: 1195: 1192: 1190: 1187: 1186: 1183: 1179: 1178: 1175: 1173: 1171: 1168: 1166: 1163: 1162: 1159: 1157: 1155: 1152: 1150: 1147: 1146: 1143: 1141: 1139: 1135: 1132: 1129: 1127: 1125: 1122: 1121: 1118: 1116: 1114: 1111: 1109: 1106: 1105: 1102: 1100: 1098: 1095: 1093: 1090: 1089: 1086: 1084: 1082: 1079: 1077: 1074: 1073: 1070: 1068: 1066: 1063: 1061: 1058: 1057: 1054: 1052: 1050: 1046: 1043: 1040: 1038: 1036: 1033: 1032: 1029: 1027: 1025: 1022: 1020: 1017: 1016: 1013: 1011: 1009: 1006: 1004: 1001: 1000: 997: 995: 993: 990: 988: 985: 984: 981: 979: 977: 973: 970: 967: 965: 963: 960: 959: 956: 954: 952: 949: 947: 944: 943: 940: 938: 936: 933: 931: 928: 927: 924: 920: 919: 916: 914: 912: 909: 907: 904: 903: 900: 898: 896: 893: 891: 888: 887: 882: 880: 878: 876: 871: 869: 867: 864: 863: 861:| BoilingPt = 860: 858: 856: 854:| BoilingPt = 853: 851: 848: 847: 842: 840: 838: 836: 831: 829: 827: 824: 823: 821:| MeltingPt = 820: 818: 816: 814:| MeltingPt = 813: 811: 808: 807: 804: 802: 800: 797: 795: 792: 791: 788: 784: 783: 781:| MolarMass = 780: 778: 776: 774:| MolarMass = 773: 771: 768: 767: 764: 762: 760: 757: 755: 752: 751: 749: 746: 744: 741: 740: 738: 735: 733: 730: 729: 727: 724: 722: 719: 718: 715: 713: 711: 708: 707: 705: 702: 700: 697: 696: 693: 691: 689: 686: 685: 682: 680: 678: 675: 673: 670: 669: 666: 664: 662: 659: 657: 654: 653: 650: 646: 645: 642: 640: 638: 635: 633: 630: 629: 626: 624: 622: 619: 617: 614: 613: 611: 608: 606: 603: 602: 599: 597: 595: 592: 590: 587: 586: 583: 581: 579: 576: 575: 572: 570: 568: 565: 564: 561: 559: 557: 554: 553: 550: 548: 546: 542: 540: 538: 535: 534: 531: 529: 527: 524: 522: 519: 518: 515: 513: 511: 508: 506: 503: 502: 499: 497: 495: 492: 491: 488: 486: 484: 481: 480: 477: 475: 473: 469: 466: 463: 461: 459: 456: 455: 451: 450:| OtherNames = 449: 447: 445: 442: 440: 437: 436: 433: 431: 429: 426: 424: 421: 420: 415: 413: 411: 409: 404: 402: 400: 397: 396: 393: 391: 389: 386: 384: 381: 380: 377: 375: 373: 369: 367: 365: 362: 361: 358: 356: 354: 351: 349: 346: 345: 341: 339: 337: 335: 331: 329: 327: 324: 323: 319:Verifiedfields 318: 316: 314: 312: 307: 305: 303: 300: 299: 296: 294: 292: 289: 287: 284: 283: 280: 276: 275: 271: 270: 254: 249: 248: 233: 212: 190: 185: 184: 169: 129: 121: 115: 99: 93: 85: 79: 76: 75: 68: 56: 50: 42: 36: 33: 32: 25: 23: 19: 18: 10: 6: 4: 3: 2: 4178: 4162: 4159: 4151: 4148: 4140: 4137: 4129: 4126: 4118: 4115: 4107: 4104: 4096: 4093: 4085: 4082: 4074: 4071: 4063: 4060: 4054: 4051: 4045: 4040: 4034: 4032: 4027: 4025: 4024: 4018: 4011: 4008: 4002: 4000: 3995: 3993: 3992: 3986: 3984: 3979: 3977: 3976: 3972: 3970: 3967: 3965: 3964: 3956: 3953: 3945: 3942: 3936: 3933: 3925: 3922: 3916: 3911: 3901: 3887: 3884: 3880: 3878: 3875: 3873: 3872: 3866: 3864: 3859: 3857: 3856: 3850: 3848: 3843: 3841: 3840: 3834: 3832: 3827: 3825: 3824: 3816: 3809: 3806: 3794: 3787: 3784: 3780: 3778: 3775: 3773: 3772: 3764: 3761: 3753: 3750: 3742: 3739: 3731: 3728: 3720: 3717: 3709: 3706: 3698: 3695: 3689:| volume = 37 3687: 3684: 3678:| journal = ] 3676: 3673: 3665: 3662: 3654: 3651: 3643: 3640: 3632: 3629: 3621: 3618: 3610: 3607: 3599: 3596: 3588: 3585: 3577: 3574: 3568:| journal = ] 3566: 3563: 3555: 3552: 3546:| year = 1999 3544: 3541: 3533: 3530: 3522: 3519: 3511: 3508: 3500: 3497: 3489: 3486: 3478: 3475: 3469:| issue = 8/9 3467: 3464: 3458:| volume = 30 3456: 3453: 3447:| journal = ] 3445: 3442: 3434: 3431: 3423: 3420: 3412: 3409: 3401: 3398: 3390: 3387: 3379: 3376: 3368: 3365: 3357: 3354: 3346: 3343: 3335: 3332: 3326:| volume = 37 3324: 3321: 3315:| journal = ] 3313: 3310: 3302: 3299: 3291: 3288: 3280: 3277: 3269: 3266: 3257: 3254: 3247: 3242: 3238: 3236: 3233: 3231: 3230: 3222: 3219: 3211: 3208: 3200: 3197: 3189: 3186: 3178: 3175: 3169:| volume = 51 3167: 3164: 3158:| journal = ] 3156: 3153: 3145: 3142: 3134: 3131: 3123: 3120: 3114: 3109: 3101: 3098: 3092: 3087: 3061: 3030: 3027: 3023: 3021: 3018: 3016: 3015: 3007: 3004: 2996: 2993: 2985: 2982: 2974: 2971: 2963: 2960: 2952: 2949: 2943:| volume = 56 2941: 2938: 2932:| journal = ] 2930: 2927: 2919: 2916: 2908: 2905: 2897: 2894: 2886: 2883: 2877: 2872: 2863: 2860: 2853: 2848: 2844: 2842: 2839: 2837: 2836: 2829: 2824: 2818: 2816: 2811: 2809: 2808: 2804: 2802: 2799: 2797: 2796: 2790: 2785: 2781: 2776: 2770: 2765: 2761: 2756: 2750: 2745: 2739: 2734: 2730: 2725: 2718: 2713: 2707: 2702: 2698: 2693: 2686: 2681: 2677: 2672: 2665: 2660: 2654: 2649: 2645: 2640: 2633: 2628: 2622: 2617: 2611: 2606: 2602: 2597: 2589: 2586: 2579: 2574: 2565: 2562: 2556: 2551: 2543: 2540: 2534: 2529: 2525: 2523: 2520: 2518: 2517: 2509: 2506: 2498: 2495: 2487: 2484: 2476: 2473: 2465: 2462: 2454: 2451: 2443: 2440: 2432: 2429: 2423:| journal = ] 2421: 2418: 2410: 2407: 2399: 2396: 2388: 2385: 2377: 2374: 2365: 2362: 2355: 2350: 2346: 2344: 2341: 2339: 2338: 2329: 2326: 2320: 2315: 2311: 2309: 2306: 2304: 2303: 2296: 2291: 2281: 2270: 2267: 2263: 2261: 2258: 2256: 2255: 2247: 2244: 2237: 2232: 2228: 2226: 2223: 2221: 2220: 2211: 2208: 2202: 2197: 2193: 2191: 2188: 2186: 2185: 2176: 2173: 2167: 2162: 2158: 2156: 2153: 2151: 2150: 2141: 2138: 2131: 2126: 2122: 2120: 2117: 2115: 2114: 2107: 2102: 2093: 2090: 2084: 2079: 2075: 2073: 2070: 2068: 2067: 2058: 2055: 2046: 2043: 2036: 2031: 2023: 2020: 2014: 2009: 2005: 2003: 2000: 1998: 1997: 1989: 1986: 1978: 1975: 1967: 1964: 1956: 1953: 1945: 1942: 1934: 1931: 1923: 1920: 1912: 1909: 1901: 1898: 1890: 1887: 1879: 1876: 1870: 1865: 1861: 1859: 1856: 1854: 1853: 1847: 1845: 1840: 1838: 1837: 1827: 1816: 1813: 1803: 1792: 1789: 1783:OtherFunction 1779: 1768: 1765: 1759: 1757: 1752: 1750: 1749: 1743: 1741: 1736: 1734: 1733: 1727: 1711: 1708: 1702: 1700: 1695: 1693: 1692: 1686: 1684: 1679: 1677: 1676: 1670: 1668: 1663: 1661: 1660: 1650: 1639: 1636: 1630: 1628: 1623: 1621: 1620: 1610: 1599: 1596: 1586: 1575: 1572: 1562: 1551: 1548: 1538: 1527: 1524: 1518: 1516: 1511: 1509: 1508: 1502: 1500: 1495: 1493: 1492: 1486: 1484: 1479: 1477: 1476: 1470: 1468: 1463: 1461: 1460: 1452: 1449: 1441: 1438: 1428: 1417: 1414: 1408: 1392: 1389: 1383: 1381: 1376: 1374: 1373: 1363: 1352: 1349: 1343: 1341: 1336: 1334: 1333: 1327: 1325: 1320: 1318: 1317: 1311: 1295: 1292: 1282: 1271: 1268: 1258: 1247: 1244: 1234: 1223: 1220: 1216:| Legal_CA = 1214: 1212: 1209:| Legal_CA = 1207: 1205: 1204: 1200:| Legal_AU = 1198: 1196: 1193:| Legal_AU = 1191: 1189: 1188: 1180: 1176:| Bioavail = 1174: 1172: 1169:| Bioavail = 1167: 1165: 1164: 1158: 1156: 1151: 1149: 1148: 1142: 1126: 1123: 1117: 1115: 1110: 1108: 1107: 1101: 1099: 1094: 1092: 1091: 1085: 1083: 1078: 1076: 1075: 1069: 1067: 1062: 1060: 1059: 1053: 1037: 1034: 1028: 1026: 1021: 1019: 1018: 1012: 1010: 1005: 1003: 1002: 996: 994: 989: 987: 986: 980: 964: 961: 955: 953: 948: 946: 945: 939: 937: 932: 930: 929: 921: 915: 913: 908: 906: 905: 899: 897: 892: 890: 889: 879: 872:Boiling_notes 868: 865: 859: 857: 852: 850: 849: 839: 832:Melting_notes 828: 825: 819: 817: 812: 810: 809: 803: 801: 796: 794: 793: 785: 779: 777: 772: 770: 769: 763: 761: 756: 754: 753: 745: 742: 734: 731: 723: 720: 714: 709: 701: 698: 692: 687: 681: 679: 674: 672: 671: 665: 663: 658: 656: 655: 647: 641: 639: 634: 632: 631: 625: 623: 618: 616: 615: 607: 604: 598: 596: 591: 589: 588: 582: 577: 571: 566: 560: 555: 549: 539: 536: 530: 528: 523: 521: 520: 514: 512: 507: 505: 504: 498: 493: 487: 482: 476: 460: 457: 448: 441: 438: 432: 430: 425: 423: 422: 412: 401: 398: 392: 390: 385: 383: 382: 376: 366: 363: 357: 355: 350: 348: 347: 338: 328: 325: 315: 308:Watchedfields 304: 301: 295: 293: 288: 286: 285: 277: 272: 252: 245: 241: 236: 227: 222: 218: 210: 204: 188: 181: 177: 172: 163: 159: 143: 136: 126:Content added 118: 16: 3789:==See also== 3700:| issue = 12 3180:| issue = 23 2285:Flocculation 1643:Autoignition 1632:| FlashPt = 1625:| FlashPt = 1454:| EUIndex = 1443:| EUClass = 1421:ExternalMSDS 1286:Pregnancy_US 1262:Pregnancy_AU 1103:| Entropy = 1096:| Entropy = 1087:| DeltaHc = 1080:| DeltaHc = 1071:| DeltaHf = 1064:| DeltaHf = 805:| Density = 798:| Density = 627:| PubChem = 620:| PubChem = 405:prop-enamide 3958:{{reflist}} 3918:{{Reflist}} 3905:References 3337:| issue = 1 2954:| issue = 8 2434:| volume = 2134:hydrolysis. 1772:OtherFunctn 1520:| NFPA-R = 1513:| NFPA-R = 1504:| NFPA-F = 1497:| NFPA-F = 1488:| NFPA-H = 1481:| NFPA-H = 1432:ExternalSDS 1367:DetonationV 643:| SMILES = 636:| SMILES = 600:| EINECS = 593:| EINECS = 416:propenamide 3191:| pages = 3068:conditions 2456:| pages = 2445:| issue = 1892:{{cite web 1704:| PEL = }} 1697:| PEL = }} 1356:ExplosiveV 1275:PregCat_US 1251:PregCat_AU 957:| pKb = }} 950:| pKb = }} 96:Revision 2 53:Revision 1 3755:| pmid = 3733:| issn = 3491:| issn = 3381:| pmid = 3213:| pmid = 3043:conducted 2998:| pmid = 2976:| issn = 2500:| pmid = 2478:| issn = 1936:| work = 1820:OtherCpds 1603:RSPhrases 683:| KEGG = 676:| KEGG = 342:446476725 332:413082188 321:= changed 310:= changed 297:{{chembox 290:{{chembox 3891:External 3799:See also 3744:| doi = 3612:| doi = 2489:| doi = 2299:polymer. 2204:==Uses== 2049:polymer. 1796:Function 1716:Section8 1688:| LD50 = 1681:| LD50 = 1614:GHS_ref 1590:PPhrases 1579:SPhrases 1566:HPhrases 1555:RPhrases 1397:Section7 1300:Section6 1185:Line 67: 1182:Line 65: 1131:Section5 1042:Section4 969:Section3 941:| pKa = 934:| pKa = 926:Line 46: 923:Line 44: 790:Line 34: 787:Line 32: 652:Line 27: 649:Line 23: 465:Section1 244:contribs 180:contribs 170:CheMoBot 141:Wikitext 3077:cooking 3071:typical 1540:| NFPA- 1529:| NFPA- 1227:PregCat 282:Line 1: 279:Line 1: 192:141,565 134:Visual 82:Page 2 72:Page 2 39:Page 1 29:Page 1 3894:links 3065:Under 3040:study 258:edits 256:1,318 194:edits 3081:does 1833:= }} 1822:= }} 1288:= }} 1277:= }} 240:talk 226:undo 221:edit 187:Bots 176:talk 162:edit 3903:== 3852:* ] 3845:* ] 3836:* ] 3829:* ] 3818:* ] 3811:* ] 3074:for 3052:not 2287:=== 2283:=== 2276:=== 2272:=== 2110:]s. 3927:* 3907:== 3896:== 3889:== 3802:== 3796:== 3034:In 1849:}} 1842:}} 1829:| 1818:| 1809:= 1805:| 1798:= 1794:| 1785:= 1781:| 1774:= 1770:| 1656:= 1652:| 1645:= 1641:| 1616:= 1612:| 1605:= 1601:| 1592:= 1588:| 1581:= 1577:| 1568:= 1564:| 1557:= 1553:| 1544:= 1533:= 1434:= 1430:| 1423:= 1419:| 1369:= 1365:| 1358:= 1354:| 1284:| 1273:| 1264:= 1260:| 1253:= 1249:| 1240:= 1236:| 1229:= 1225:| 885:= 881:| 874:= 870:| 845:= 841:| 834:= 830:| 694:}} 317:| 306:| 242:| 178:| 4164:] 4153:] 4142:] 4131:] 4120:] 4109:] 4098:] 4087:] 4076:] 4065:] 4047:] 4036:] 4029:] 4020:] 4013:] 4004:] 3997:] 3988:] 3981:] 3037:a 1719:= 1713:| 1542:S 1531:O 1400:= 1394:| 1303:= 1297:| 1134:= 1128:| 1045:= 1039:| 972:= 966:| 541:| 468:= 462:| 418:) 407:) 264:m 246:) 238:( 182:) 174:(

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