Cocamidopropyl betaine
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2008-06-14T04:52:57Z
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{{Chembox new
| Name = Cocamidopropyl betaine
| ImageFile = Cocamidopropyl betaine2.png
<!-- | ImageSize = 350px -->
| ImageName = Cocamidopropyl betaine
| IUPACName = {[3-(dodecanoylamino)propyl]
(dimethyl)ammonio}acetate
| Section1 = {{Chembox Identifiers
| CASNo = 86438-79-1
| SMILES = CCCCCCCCCCCC(=O)NCCC[N+](C)(C)CC(=O)[O-]
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>19</sub>H<sub>38</sub>N<sub>2</sub>O<sub>3</sub>
| MolarMass = 342.52 g/mol
| Density = x.xxx g/cm<sup>3</sup>
| MeltingPt =
| BoilingPt =
}}
}}
'''Cocamidopropyl betaine''' ('''CAPB''') is a [[zwitterion]]ic [[surfactant]] with a [[quaternary ammonium cation]] in its molecule. It is a viscous pale yellow transparent liquid and is used as a [[surfactant]] in bath products like [[shampoo]]s and [[hand soap]]s, and in [[cosmetics]] as an [[emulsifying agent]] and [[thickener]], and to reduce irritation purely ionic surfactants would cause. It also serves as an [[antistatic agent]] in [[hair conditioner]]s.
Cocamidopropyl betaine is a derivate of [[cocamide]] and [[glycine betaine]] (a form of [[Betaines|betaine]]). See [[cocamide]] for the discussion of the length of carbon chain in the molecule.
Cocamidopropyl betaine is a medium strength surfactant which most often does not irritate [[skin]] or [[mucous membrane]]s. That said, some studies indicate it is an allergen.<ref name="deGroot"/><ref name="BrandR"/><ref name="Mowad"/> It also has [[antiseptic]] properties, making it suitable for personal sanitary products. It is compatible with other cationic, anionic, and nonionic surfactants.
Cocamidopropyl betaine to a significant degree has replaced [[cocamide DEA]].
Cocamidopropyl betaine is the active ingredient in [[Johnson & Johnson]]'s [[Baby wash]].
==CAPB Specification==
CAPB is obtained as an aqueous solution in concentrations of about 30%.
*Active ingredient 29.5 – 32.5%
*[[Water]] 62 – 66%
*[[Sodium chloride|NaCl]] 4.6 – 5.6%
Typical impurities of leading manufacturers today:
*[[chloroacetic acid|Sodium monochloroacetate]] < 5 ppm
*[[Amidoamine]] (AA) < 0.3%
*[[dimethylaminopropylamine]] (DMAPA) < 15 ppm
*[[Glycerol]] < 3%
However, there are qualities in the market with up to 3% AA.
The impurities AA and DMAPA are most critical, as they have been shown to be responsible for skin sensitation reactions. These by-products can be avoided by a moderate excess chloroacetate and the exact adjustment of pH value during betainization reaction accompanied by regular analytical control.
==Safety concerns relating to CAPB==
CAPB has been claimed to cause allergic reactions in some users,<ref name="deGroot">de Groot AC, van der Walle HB, Weyland JW. Contact allergy to cocamidopropyl betaine. ''Contact Dermatitis.'' 1995 Dec;33(6):419-22. PMID 8706401</ref><ref name="BrandR">Brand R, Delaney TA. Allergic contact dermatitis to cocamidopropylbetaine in hair shampoo. ''Australas J Dermatol.'' 1998 May;39(2):121-2. PMID 9611386</ref><ref name="Mowad">Mowad CM.Cocamidopropyl betaine allergy. ''Am J Contact Dermat.'' 2001 Dec;12(4):223-4. PMID 11753899</ref> but a controlled pilot study has found that these cases may represent irritant reactions rather than true allergic reactions.<ref name="ShafferKK">Shaffer KK, Jaimes JP, Hordinsky MK, Zielke GR, Warshaw EM. Allergenicity and cross-reactivity of coconut oil derivatives: A double-blind randomized controlled pilot study. Department of Dermatology, School of Medicine, University of Minnesota, MN, USA. ''Dermatitis.'' 2006 Jun;17(2):71-6. PMID 16956456</ref> Furthermore, results of human studies have shown that CAPB has a low sensitizing potential if impurities with [[amidoamine]] (AA) and [[dimethylaminopropylamine]] (DMAPA) are low and tightly controlled.<ref name="FowlerJF">Fowler JF Jr, Zug KM, Taylor JS, Storrs FJ, Sherertz EA, Sasseville DA, Rietschel RL, Pratt MD, Mathias CG, Marks JG, Maibach HI, Fransway AF, Deleo VA, Belsito DV. Allergy to cocamidopropyl betaine and amidoamine in North America. ''Dermatitis''. 2004 Mar;15(1):5-6. PMID 15573641</ref><ref name="Koting">Korting HC, Parsch EM, Enders F, Przybilla B. Allergic contact dermatitis to cocamidopropyl betaine in shampoo. Department of Dermatology, Ludwig-Maximilians University Munich, Germany. ''J Am Acad Dermatol.'' 1992 Dec;27(6 Pt 1):1013-5. PMID 1479082</ref> Other studies have concluded that most apparent allergic reactions to CAPB are more likely due to amidoamine.<ref name="Fowler_JF">Fowler JF, Fowler LM, Hunter JE, Allergy to cocamidopropyl betaine may be due to amidoamine: a patch test and product use test study. Family & Occupational Dermatology, Inc., Louisville, Kentucky 40202, USA. ''Contact Dermatitis''. 1997 Dec;37(6):276-81. PMID 9455630</ref><ref name="FotiC">Foti C, Bonamonte D, Mascolo G, Corcelli A, Lobasso S, Rigano L, Angelini G. The role of 3-dimethylaminopropylamine and amidoamine in contact allergy to cocamidopropylbetaine. ''Contact Dermatitis.'' 2003 Apr;48(4):194-8. PMID 12786723 {{PDFlink|[http://www.biologia.uniba.it/fisiologia/corcelli/en/pdf/contact%20dermatitis.pdf full text]|92.0 [[Kibibyte|KiB]]<!-- application/pdf, 94282 bytes -->}}</ref>
==References==
<references />
==External links==
*[http://www.cosmeticsdatabase.com/ingredient.php?ingred_id=4912 Environmental Working Group: Safety reviews of common ingredients]
[[Category:Surfactants]]
[[Category:Antiseptics]]
[[Category:Cosmetic chemicals]]
[[Category:Antistatic agents]]
[[Category:Quaternary ammonium compounds]]
[[nl:Cocamidopropyl betaïne]]