Cocamidopropyl betaine

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Lauramidopropyl betaine
Structural formula of lauramidopropyl betaine
Lauramidopropyl betaine, the major component of cocamidopropyl betaine
Names
IUPAC name
{[3-(Dodecanoylamino)propyl](dimethyl)ammonio}acetate
Other names
2-[(3-Dodecanamidopropyl)dimethylaminio]acetate
Identifiers
61789-40-0 YesY
ChemSpider 19106 YesY
EC Number 263-058-8
Jmol 3D model Interactive image
Interactive image
Interactive image
PubChem 20280
  • InChI=1S/C19H38N2O3/c1-4-5-6-7-8-9-10-11-12-14-18(22)20-15-13-16-21(2,3)17-19(23)24/h4-17H2,1-3H3,(H-,20,22,23,24) YesY
    Key: MRUAUOIMASANKQ-UHFFFAOYSA-N YesY
  • InChI=1/C19H38N2O3/c1-4-5-6-7-8-9-10-11-12-14-18(22)20-15-13-16-21(2,3)17-19(23)24/h4-17H2,1-3H3,(H-,20,22,23,24)
    Key: MRUAUOIMASANKQ-UHFFFAOYAL
  • CCCCCCCCCCCC(=O)NCCC[N+](C)(C)CC([O-])=O
  • CCCCCCCCCCCC(=O)NCCC[N+](C)(C)CC(=O)[O-]
  • [O-]C(=O)C[N+](CCCNC(=O)CCCCCCCCCCC)(C)C
Properties
C19H38N2O3
Molar mass 342.52 g·mol−1
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Cocamidopropyl betaine (CAPB) is an organic compound derived from coconut oil and dimethylaminopropylamine.[1] It is a zwitterion, consisting of both a quaternary ammonium cation and a carboxylate. CAPB is available as viscous pale yellow solution that is used as a surfactant in personal care products. The name reflects that the major part of the molecule, the lauric acid group, is derived from coconut oil. Cocamidopropyl betaine to a significant degree has replaced cocamide DEA.

Production

Cocamidopropyl betaine can be viewed as the combination of cocamide and glycine betaine. It is however prepared by combining chloroacetic acid with the amide derived from dimethylaminopropylamine and lauric acid:

CH3(CH2)10C(O)N(H)CH2CH2CH2N(CH3)2 + ClCH2CO2H + NaOH → CH3(CH2)10C(O)N(H)CH2CH2CH2N+(CH3)2CH2CO2 + NaCl + H2O

Specifications and properties

Cocamidopropyl betaine is used as a foam booster in shampoos.[2] It is a medium strength surfactant also used in bath products like hand soaps. It is also used 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 conditioners. which most often does not irritate skin or mucous membranes. However, some studies indicate it is an allergen.[3][4][5] It also has antiseptic properties, making it suitable for personal sanitary products. It is compatible with other cationic, anionic, and nonionic surfactants.

CAPB is obtained as an aqueous solution in concentrations of about 30%.

  • Active *NaCl 4.6 – 5.6%

Typical impurities of leading manufacturers today:

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

CAPB has been claimed to cause allergic reactions in some users,[3][4][5] but a controlled pilot study has found that these cases may represent irritant reactions rather than true allergic reactions.[6] 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.[7][8] Other studies have concluded that most apparent allergic reactions to CAPB are more likely due to amidoamine.[9][10] Cocamidopropyl betaine was voted 2004 Allergen of the Year by the American Contact Dermatitis Society.[11]

See also

References

  1. Christian Nitsch, Hans-Joachim Heitland, Horst Marsen, Hans-Joachim Schlüussler, "Cleansing Agents" in Ullmann’s Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a07_137
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  11. History of Allergen of the Year. contactderm.org