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Revision as of 14:09, 22 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 461847139 of page Polyacrylic_acid for the Chem/Drugbox validation project (updated: 'KEGG').  Latest revision as of 23:07, 3 January 2025 edit 38.49.72.163 (talk) →Production: update verb tense 
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{{short description|Anionic polyelectrolyte polymer}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{redirect|Carbomer|the exotic molecules expanded by insertion of two-carbon units|Carbo-mer}}
{{chembox
{{Chembox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 434001357
| verifiedrevid = 461939333
| Name = Poly(acrylic acid)
| ImageFile1 = Polyacrylic acid.png | Name = Poly(acrylic acid)
| ImageSize1 = 200px | ImageFile =
| ImageName2 = Segment of Poly(acrylic acid) | ImageFile1 = Polyacrylic acid.svg
| ImageSize1 = 170px
| IUPACName =
| ImageName2 = Segment of Poly(acrylic acid)
| OtherNames =
| IUPACName = Poly(acrylic acid), poly(1-carboxyethylene)
| OtherNames = PAA, PAAc, Acrysol, Acumer, Alcosperse, Aquatreat, Carbomer, Sokalan
| SystematicName =
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| SMILES = | SMILES =
| CASNo = 9003-01-4 | CASNo = 9003-01-4
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| RTECS = | ChEBI = 51133
| EINECS = 618-347-7
| KEGG_Ref = {{keggcite|correct|kegg}}
| UNII1_Ref = {{fdacite|changed|FDA}}
| KEGG = <!-- blanked - oldvalue: C19501 -->
| UNII1 = 73861X4K5F
| UNII1_Comment = (8000 MW)
| PubChem =
| RTECS =
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C19501
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| ChemSpiderID = NA | ChemSpiderID = none
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| Formula = (C<sub>3</sub>H<sub>4</sub>O<sub>2</sub>)<sub>n</sub> | Formula = (C<sub>3</sub>H<sub>4</sub>O<sub>2</sub>)<sub>n</sub>
| MolarMass = variable | MolarMass = variable
| Appearance = | Appearance =
| Density = | Density =
| Solubility = | Solubility =
| MeltingPtC = | MeltingPtC =
| BoilingPtC = | BoilingPtC =
| Viscosity = | Viscosity =
| LogP = 0.25700<ref name="chemsrc">{{Cite web|url=https://www.chemsrc.com/en/cas/9003-01-4_453957.html|title=Polyacrylic acid_msds|access-date=2018-04-23|archive-date=2022-02-21|archive-url=https://web.archive.org/web/20220221133709/https://www.chemsrc.com/en/cas/9003-01-4_453957.html|url-status=live}}</ref>
}}
}}
| Section3 = {{Chembox Structure | Section3 = {{Chembox Structure
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| Dipole = | Dipole =
}} }}
| Section4 =
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| Section6 =
| Section7 = {{Chembox Hazards | Section7 = {{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
| NFPA-H = 0
| EUClass = {{Hazchem Xi}}
| NFPA-H = | NFPA-F = 0
| NFPA-F = | NFPA-R = 0
| Hazards_ref=<ref>{{cite web |title=C&L Inventory |url=https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/45007 |website=echa.europa.eu |access-date=2021-12-05 |archive-date=2021-04-05 |archive-url=https://web.archive.org/web/20210405145448/https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/45007 |url-status=live }}</ref>
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| RPhrases = {{R36}} {{R37}} {{R38}} | GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
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| HPhrases = {{H-phrases|315|319|335}}
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'''Poly(acrylic acid)''' ('''PAA'''; trade name '''Carbomer''') is a ] with the formula (CH<sub>2</sub>−CHCO<sub>2</sub>H)<sub>''n''</sub>. It is a derivative of ] (CH<sub>2</sub>=CHCO<sub>2</sub>H). In addition to the ]s, a variety of copolymers and crosslinked polymers, and partially deprotonated derivatives thereof, are known and of commercial value. In a water solution at neutral ], PAA is an ] ], i.e., many of the side chains of PAA lose their protons and acquire a negative charge. Partially or wholly deprotonated PAAs are ]s, with the ability to absorb and retain water and swell to many times their original volume. These properties{{snd}} acid–base and water-attracting{{snd}} are the basis of many applications.

== Synthesis ==
PAA, like any ], is usually synthesized through a process known as free radical polymerization,<ref>{{Cite journal |last1=Zhang |first1=Rongguo |last2=Li |first2=Qiong |last3=Zhang |first3=Anfu |last4=Liu |first4=Yong |last5=Lei |first5=Jiaheng |date=2008-12-01 |title=The synthesis technique of polyacrylic acid superplasticizer |url=https://doi.org/10.1007/s11595-008-6830-y |journal=Journal of Wuhan University of Technology-Mater. Sci. Ed. |language=en |volume=23 |issue=6 |pages=830–833 |doi=10.1007/s11595-008-6830-y |s2cid=93458743 |issn=1993-0437}}</ref><ref>{{Cite journal |last1=Hu |first1=Yong |last2=Jiang |first2=Xiqun |last3=Ding |first3=Yin |last4=Ge |first4=Haixiong |last5=Yuan |first5=Yuyan |last6=Yang |first6=Changzheng |date=2002-08-01 |title=Synthesis and characterization of chitosan–poly(acrylic acid) nanoparticles |url=https://www.sciencedirect.com/science/article/pii/S0142961202000716 |journal=Biomaterials |volume=23 |issue=15 |pages=3193–3201 |doi=10.1016/S0142-9612(02)00071-6 |pmid=12102191 |issn=0142-9612}}</ref> though graft polymerization may also be used.<ref>{{Cite journal |last1=Li |first1=An |last2=Wang |first2=Aiqin |last3=Chen |first3=Jianmin |date=2004-05-05 |title=Studies on poly(acrylic acid)/attapulgite superabsorbent composite. I. Synthesis and characterization |url=https://onlinelibrary.wiley.com/doi/10.1002/app.20104 |journal=Journal of Applied Polymer Science |language=en |volume=92 |issue=3 |pages=1596–1603 |doi=10.1002/app.20104 |issn=0021-8995}}</ref><ref>{{Cite journal |last1=Lin |first1=Jianming |last2=Wu |first2=Jihuai |last3=Yang |first3=Zhengfang |last4=Pu |first4=Minli |date=2001-03-01 |title=Synthesis and Properties of Poly(acrylic acid)/Mica Superabsorbent Nanocomposite |url=https://onlinelibrary.wiley.com/doi/10.1002/1521-3927(20010301)22:63.0.CO;2-R |journal=Macromolecular Rapid Communications |language=en |volume=22 |issue=6 |pages=422–424 |doi=10.1002/1521-3927(20010301)22:6<422::AID-MARC422>3.0.CO;2-R |issn=1022-1336}}</ref> Free radical polymerization involves the conversion of monomers, in this case, acrylic acid (CH<sub>2</sub>=CHCO<sub>2</sub>H), into a polymer chain through the action of free radicals.<ref>{{Cite journal |last1=Bromberg |first1=Lev E. |last2=Barr |first2=David P. |date=1999-06-01 |title=Aggregation Phenomena in Aqueous Solutions of Hydrophobically Modified Polyelectrolytes. A Probe Solubilization Study |url=https://pubs.acs.org/doi/10.1021/ma981946k |journal=Macromolecules |language=en |volume=32 |issue=11 |pages=3649–3657 |doi=10.1021/ma981946k |bibcode=1999MaMol..32.3649B |issn=0024-9297}}</ref><ref>{{Citation |last1=Laschewsky |first1=André |title=Stars and Blocks: Tailoring Polymeric Rheology Modifiers for Aqueous Media by Controlled Free Radical Polymerization |date=January 2003 |url=https://pubs.acs.org/doi/abs/10.1021/bk-2013-1148.ch008 |work=ACS Symposium Series |volume=1148 |pages=125–143 |editor-last=Patil |editor-first=Anjali |access-date=2023-12-20 |place=Washington, DC |publisher=American Chemical Society |language=en |doi=10.1021/bk-2013-1148.ch008 |isbn=978-0-8412-2905-1 |last2=Herfurth |first2=Christoph |last3=Miasnikova |first3=Anna |last4=Stahlhut |first4=Frank |last5=Weiss |first5=Jan |last6=Wieland |first6=Christoph |last7=Wischerhoff |first7=Erik |last8=Gradzielski |first8=Michael |last9=Malo de Molina |first9=Paula |editor2-last=Ferritto |editor2-first=Michael S.}}</ref><ref>{{Citation |last1=Iqbal |first1=Hafiz M. N. |title=Design and Processing Aspects of Polymer and Composite Materials |date=2018-10-03 |url=https://onlinelibrary.wiley.com/doi/10.1002/9781119407089.ch7 |work=Green and Sustainable Advanced Materials |pages=155–189 |editor-last=Ahmed |editor-first=Shakeel |access-date=2023-12-20 |edition=1 |publisher=Wiley |language=en |doi=10.1002/9781119407089.ch7 |isbn=978-1-119-40708-9 |last2=Rasheed |first2=Tahir |last3=Bilal |first3=Muhammad |s2cid=139704996 |editor2-last=Hussain |editor2-first=Chaudhery Mustansar}}</ref> The process typically follows these steps:<ref>{{Cite journal |last1=Liu |first1=Ke |last2=Corrigan |first2=Nathaniel |last3=Postma |first3=Almar |last4=Moad |first4=Graeme |last5=Boyer |first5=Cyrille |date=2020-10-27 |title=A Comprehensive Platform for the Design and Synthesis of Polymer Molecular Weight Distributions |url=https://pubs.acs.org/doi/10.1021/acs.macromol.0c01954 |journal=Macromolecules |language=en |volume=53 |issue=20 |pages=8867–8882 |doi=10.1021/acs.macromol.0c01954 |bibcode=2020MaMol..53.8867L |s2cid=225117544 |issn=0024-9297}}</ref>

# ]: Free radicals are generated by initiators such as ] (]]) or ] (AIBN). These radicals are highly reactive and can start the polymerization process by reacting with the monomer units.<ref>{{Cite journal |last1=Plamper |first1=Felix A. |last2=Becker |first2=Harald |last3=Lanzendörfer |first3=Michael |last4=Patel |first4=Mushtaq |last5=Wittemann |first5=Alexander |last6=Ballauff |first6=Matthias |last7=Müller |first7=Axel H. E. |date=2005-09-23 |title=Synthesis, Characterization and Behavior in Aqueous Solution of Star-Shaped Poly(acrylic acid) |url=https://onlinelibrary.wiley.com/doi/10.1002/macp.200500238 |journal=Macromolecular Chemistry and Physics |language=en |volume=206 |issue=18 |pages=1813–1825 |doi=10.1002/macp.200500238 |issn=1022-1352}}</ref>
# ]: Once the radical reacts with a monomer, it creates a new radical at the end of the growing chain. This new radical can react with additional monomer units, allowing the chain to grow.<ref>{{Cite journal |last1=Cuti |first1=Sergio S. |last2=Henton |first2=David E. |last3=Powell |first3=Cynthia |last4=Reim |first4=Robert E. |last5=Smith |first5=Patrick |last6=Staples |first6=Thomas L. |date=1997-04-18 |title=The effects of MEHQ on the polymerization of acrylic acid in the preparation of superabsorbent gels |url=https://onlinelibrary.wiley.com/doi/10.1002/(SICI)1097-4628(19970418)64:33.0.CO;2-V |journal=Journal of Applied Polymer Science |language=en |volume=64 |issue=3 |pages=577–589 |doi=10.1002/(SICI)1097-4628(19970418)64:3<577::AID-APP14>3.0.CO;2-V |issn=0021-8995}}</ref>
# ]: The reaction continues until two radicals recombine, or a radical is transferred to another molecule, terminating the growth of the polymer chain.<ref>{{Cite journal |last1=Luciani |first1=Carla |last2=Choi |first2=Kyu Yong |date=September 2023|title=Modelling of a continuous kneader reactor for the polymerization of partially neutralized acrylic acid |url=https://onlinelibrary.wiley.com/doi/10.1002/cjce.24898 |journal=The Canadian Journal of Chemical Engineering |language=en |volume=101 |issue=9 |pages=5151–5161 |doi=10.1002/cjce.24898 |s2cid=257729740 |issn=0008-4034}}</ref>
# ] and ]: Other reactions can also occur, such as chain transfer (where the radical is transferred to a different molecule, creating a new radical) or inhibition (where impurities stop the growth of the chain).<ref>{{Cite journal |last1=Nicolaÿ |first1=Renaud |last2=Mosnáček |first2=Jaroslav |last3=Kar |first3=Kishore K. |last4=Fruchey |first4=Stanley O. |last5=Cloeter |first5=Michael D. |last6=Harner |first6=Richard S. |last7=Matyjaszewski |first7=Krzysztof |date=2012-03-28 |title=Efficient Polymerization Inhibition Systems for Acrylic Acid Distillation: Vapor-Phase Inhibitors |url=https://pubs.acs.org/doi/10.1021/ie201709y |journal=Industrial & Engineering Chemistry Research |language=en |volume=51 |issue=12 |pages=4467–4471 |doi=10.1021/ie201709y |issn=0888-5885}}</ref>

== Production ==
The global market was estimated to be worth $3.4 billion in 2022.<ref>{{Cite web |title=Polyacrylic Acid Market Demand, Key Players, Opportunities, & Forecast Analysis By 2029 |url=https://www.databridgemarketresearch.com/reports/global-polyacrylic-acid-market |access-date=2023-12-20 |website=www.databridgemarketresearch.com}}</ref><ref>{{Cite web |last=ltd |first=Research and Markets |title=Polyacrylic Acid - Global Strategic Business Report |url=https://www.researchandmarkets.com/reports/5140057/polyacrylic-acid-global-strategic-business |access-date=2023-12-20 |website=www.researchandmarkets.com |language=english}}</ref>

==Structure and derivatives==
Polyacrylic acid is a weak anionic polyelectrolyte, whose degree of ] is dependent on solution pH. In its non-ionised form at low pHs, PAA may associate with various non-ionic polymers (such as polyethylene oxide, poly-N-vinyl pyrrolidone, polyacrylamide, and some cellulose ethers) and form hydrogen-bonded interpolymer ].<ref>{{Cite book|last1=Khutoryanskiy|first1=Vitaliy V.|url=https://books.google.com/books?id=blrICgAAQBAJ|title=Hydrogen-bonded Interpolymer Complexes: Formation, Structure And Applications|last2=Staikos|first2=Georgios|date=9 March 2009|publisher=World Scientific|isbn=978-981-4475-04-4|language=en|oclc=1200871469|access-date=2022-02-21|archive-date=2022-02-21|archive-url=https://web.archive.org/web/20220221134049/https://books.google.com/books?id=blrICgAAQBAJ&newbks=0&hl=en|url-status=live}}</ref> In aqueous solutions PAA can also form polycomplexes with oppositely charged polymers such as chitosan, surfactants, and drug molecules (for example, streptomycin).<ref>{{cite journal|last1=Nurkeeva|first1=Zauresh S|last2=Khutoryanskiy|first2=Vitaliy V|last3=Mun|first3=Grigoriy A|last4=Sherbakova|first4=Marina V|last5=Ivaschenko|first5=Anatoliy T|last6=Aitkhozhina|first6=Nazira A|date=March 2004|title=Polycomplexes of poly(acrylic acid) with streptomycin sulfate and their antibacterial activity|url=https://pubmed.ncbi.nlm.nih.gov/15018981/|url-status=live|journal=European Journal of Pharmaceutics and Biopharmaceutics|volume=57|issue=2|pages=245–9|doi=10.1016/S0939-6411(03)00149-8|pmid=15018981|archive-url=https://web.archive.org/web/20220221131828/https://pubmed.ncbi.nlm.nih.gov/15018981/|archive-date=21 February 2022|via=PubMed, Elsevier}}</ref>

== Physical properties ==
Dry PAAs are sold as white, fluffy powders.

== Derivatives ==
In the dry powder form of ], the positively charged sodium ions are bound to the ], however, in aqueous solutions the sodium ions can dissociate. The presence of sodium cations allows the polymer to absorb a high amount of water.

== Applications ==

=== Absorbent ===
PAA is widely used in dispersants. Its molecular weight has a significant impact on the rheological properties and dispersion capacity, and hence applications. The dominant application for PAA is as a ]. About 25% of PAA is used for detergents and dispersants.

Polyacrylic acid and its derivatives (particularly ]) are used in ]. Acrylic acid is also the main component of Superabsorbent Polymers (SAPs), which are cross-linked polyacrylates that can absorb and retain more than 100 times of their own weight in liquid. The US Food and Drug Administration authorised the use of SAPs in packaging with indirect food contact.<ref>{{cite book|last1=Orwoll|first1=Robert A.|url=https://books.google.com/books?id=qFi5QgAACAAJ|title=Polymer Data Handbook|last2=Yong|first2=Chong S.|publisher=Oxford University Press, Inc.|year=1999|isbn=978-0195107890|editor-last=Mark|editor-first=James E.|pages=252–253|chapter=Poly(acrylic acid)|oclc=39962426|access-date=2022-02-21|archive-date=2022-02-21|archive-url=https://web.archive.org/web/20220221134046/https://www.google.co.in/books/edition/Polymer_Data_Handbook/qFi5QgAACAAJ?hl=en|url-status=live}}</ref><ref>{{cite web|date=2005|title=Acrylates|url=http://pslc.ws/macrog/acrylate.htm|url-status=live|archive-url=https://web.archive.org/web/20220221130123/https://pslc.ws/macrog/acrylate.htm|archive-date=21 February 2022|access-date=25 June 2015|website=The Macrogalleria|publisher=Polymer Science Learning Center}}</ref>

=== Cleaning ===
Detergents often contain copolymers of acrylic acid that assist in sequestering dirt. Cross-linked polyacrylic acid has also been used in the production of household products, including floor cleaners.
PAA may inactivate the ] ].<ref>{{cite journal|last1=Kaiser|first1=Nancy|last2=Klein|first2=Dan|last3=Karanja|first3=Peter|last4=Greten|first4=Zachariah|last5=Newman|first5=Jerry|year=2009|title=Inactivation of chlorhexidine gluconate on skin by incompatible alcohol hand sanitizing gels|url=https://pubmed.ncbi.nlm.nih.gov/19398245|url-status=live|journal=American Journal of Infection Control|volume=37|issue=7|pages=569–73|doi=10.1016/j.ajic.2008.12.008|pmid=19398245|archive-url=https://web.archive.org/web/20211219103024/https://pubmed.ncbi.nlm.nih.gov/19398245/|archive-date=19 December 2021|via=PubMed, Elsevier}}</ref>

=== Biocompatible materials ===
The neutralized polyacrylic acid gels are suitable biocompatible matrices for medical applications such as gels for skin care products. PAA films can be deposited on orthopaedic implants to protect them from corrosion. Crosslinked hydrogels of PAA and gelatin have also been used as medical glue.

=== Paints and cosmetics ===
Other applications involve ]s and ]. They stabilize suspended solid in liquids,<ref>{{Cite journal |last1=Kuila |first1=Debasish |last2=Blay |first2=George A. |last3=Borjas |first3=Ricardo E. |last4=Hughes |first4=Steve |last5=Maddox |first5=Phil |last6=Rice |first6=Kay |last7=Stansbury |first7=Wayne |last8=Laurel |first8=Norma |date=1999-08-15 |title=Polyacrylic acid (poly-A) as a chelant and dispersant |url=https://onlinelibrary.wiley.com/doi/10.1002/(SICI)1097-4628(19990815)73:73.0.CO;2-F |journal=Journal of Applied Polymer Science |language=en |volume=73 |issue=7 |pages=1097–1115 |doi=10.1002/(SICI)1097-4628(19990815)73:7<1097::AID-APP2>3.0.CO;2-F |issn=0021-8995}}</ref> prevent emulsions from separating, and control the consistency in flow of cosmetics. Carbomer codes (910, 934, 940, 941, and 934P) are an indication of molecular weight and the specific components of the polymer. For many applications PAAs are used in form of ] or ammonium salts, e.g. ].

===Emerging applications===
Hydrogels derived from PAA have attracted much study for use as bandages and aids for wound healing.<ref>{{cite journal|last1=Mogoşanu|first1=George Dan|last2=Grumezescu|first2=Alexandru Mihai|date=25 March 2014|title=Natural and synthetic polymers for wounds and burns dressing|url=https://pubmed.ncbi.nlm.nih.gov/24368109|url-status=live|journal=International Journal of Pharmaceutics|volume=463|issue=2|pages=127–136|doi=10.1016/j.ijpharm.2013.12.015|pmid=24368109|archive-url=https://web.archive.org/web/20220201193137/https://pubmed.ncbi.nlm.nih.gov/24368109/|archive-date=1 February 2022}}</ref>

=== Drilling fluid and metal quenching ===
{{Main|Sodium polyacrylate}}
A few reports were made on PAA use as ] (so called ]ne ]) for oil drilling industry.<ref>{{Cite web |date= |title=Deflocculants: A Detailed Overview |url=https://digitalfire.com/article/deflocculants%3A+a+detailed+overview |archive-url=https://web.archive.org/web/20210226073325/https://digitalfire.com/article/deflocculants%3A+a+detailed+overview |archive-date=February 26, 2021}}</ref><ref>{{Cite journal |last1=Petrov |first1=N.A. |last2=Maikobi |first2=A.A. |date=December 2017 |title=Investigation of Uniflox Reagent for Drilling Siberian Solvent Solutions |url=http://ogbus.ru/article/issledovanie-reagenta-uniflok-dlya-burovyx-rastvorov-zapadnoj-sibiriinvestigation-of-uniflox-reagent-for-drilling-siberian-solvent-solutions/ |journal=Oil and Gas Business |issue=6 |pages=6–19 |doi=10.17122/ogbus-2017-6-6-19 |doi-broken-date=1 November 2024 |access-date=2022-05-06 |archive-date=2018-06-21 |archive-url=https://web.archive.org/web/20180621140042/http://ogbus.ru/article/issledovanie-reagenta-uniflok-dlya-burovyx-rastvorov-zapadnoj-sibiriinvestigation-of-uniflox-reagent-for-drilling-siberian-solvent-solutions/ |url-status=dead }}</ref>

It was also reported to be used for metal ] in metalworking (see ]).<ref>{{Cite thesis |title=The quenching characteristics of sodium polyacrylate solutions. |url=http://shura.shu.ac.uk/19731/ |publisher=Sheffield Hallam University |date=1989 |place=Sheffield |degree=doctoral |language=en |first=W. D. |last=Griffiths}}</ref>

==References==
{{Reflist}}

{{Plastics}}

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