Cocamidopropyl betaine

Last updated
Lauramidopropyl betaine
Cocamidopropyl betaine.svg
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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.057.308 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 263-058-8
PubChem CID
UNII
  • 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) Yes check.svgY
    Key: MRUAUOIMASANKQ-UHFFFAOYSA-N Yes check.svgY
  • 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 342.524 g·mol−1
AppearanceClear to slight yellow liquid [1]
Density 1.05 g/cm3
Melting point <−10 °C (14 °F; 263 K) [1]
Boiling point >100 °C (212 °F; 373 K) [1]
Soluble [1]
Viscosity < 100 cP (30°C) [1]
Hazards
GHS labelling:
GHS-pictogram-pollu.svg [1]
Warning [1]
H315, H319, H400 [1]
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Cocamidopropyl betaine (CAPB) is a mixture of closely related organic compounds derived from coconut oil and dimethylaminopropylamine. [2] CAPB is available as a viscous pale yellow solution and it is used as a surfactant in personal care products and animal husbandry. 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.

Contents

Production

Despite the name cocamidopropyl betaine, the molecule is not synthesized from betaine. Instead it is produced in a two step manner, beginning with the reaction of dimethylaminopropylamine (DMAPA) with fatty acids from coconut or palm kernel oil (lauric acid, or its methyl ester, is the main constituent). The primary amine in DMAPA is more reactive than the tertiary amine, leading to its selective addition to form an amide. In the second step chloroacetic acid reacts with the remaining tertiary amine to form a quaternary ammonium center (a quaternization reaction). [3]

CH3(CH2)10COOH + H2NCH2CH2CH2N(CH3)2 → CH3(CH2)10CONHCH2CH2CH2N(CH3)2
CH3(CH2)10CONHCH2CH2CH2N(CH3)2 + ClCH2CO2H + NaOH → CH3(CH2)10CONHCH2CH2CH2N+(CH3)2CH2CO2− + NaCl + H2O

Chemistry

CAPB is a fatty acid amide containing a long hydrocarbon chain at one end and a polar group at the other. This allows CAPB to act as a surfactant and as a detergent. It is a zwitterion, consisting of both a quaternary ammonium cation and a carboxylate.[ citation needed ]

Specifications and properties

Cocamidopropyl betaine is used as a foam booster in shampoos. [4] 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. [5] [6] [7]

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

Typical impurities of leading manufacturers today:

The impurities AA and DMAPA are most critical, as they have been shown to be responsible for skin sensitization 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.

Niche Uses

CAPB is also used as a co-surfactant with Sodium dodecyl sulfate for promoting the formation of gas hydrates. [8] CAPB, as an additive, helps to scale-up the gas hydrates' formation process. [9]

Safety

CAPB has been claimed to cause allergic reactions in some users, [5] [6] [7] but a controlled pilot study has found that these cases may represent irritant reactions rather than true allergic reactions. [10] 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. [11] [12] Other studies have concluded that most apparent allergic reactions to CAPB are more likely due to amidoamine. [13] [14] Cocamidopropyl betaine was voted 2004 Allergen of the Year by the American Contact Dermatitis Society. [15]

See also

Related Research Articles

Sodium laureth sulfate (SLES), an accepted contraction of sodium lauryl ether sulfate (SLES), also called sodium alkylethersulfate, is an anionic detergent and surfactant found in many personal care products and for industrial uses. SLES is an inexpensive and very effective foaming agent. SLES, sodium lauryl sulfate (SLS), ammonium lauryl sulfate (ALS), and sodium pareth sulfate are surfactants that are used in many cosmetic products for their cleaning and emulsifying properties. It is derived from palm kernel oil or coconut oil. In herbicides, it is used as a surfactant to improve absorption of the herbicidal chemicals and reduces time the product takes to be rainfast, when enough of the herbicidal agent will be absorbed.

<span class="mw-page-title-main">Contact dermatitis</span> Human disease

Contact dermatitis is a type of acute or chronic inflammation of the skin caused by exposure to chemical or physical agents. Symptoms of contact dermatitis can include itchy or dry skin, a red rash, bumps, blisters, or swelling. These rashes are not contagious or life-threatening, but can be very uncomfortable.

<span class="mw-page-title-main">Quaternary ammonium cation</span> Polyatomic ions of the form N(–R)₄ (charge +1)

In organic chemistry, quaternary ammonium cations, also known as quats, are positively-charged polyatomic ions of the structure [NR4]+, where R is an alkyl group, an aryl group or organyl group. Unlike the ammonium ion and the primary, secondary, or tertiary ammonium cations, the quaternary ammonium cations are permanently charged, independent of the pH of their solution. Quaternary ammonium salts or quaternary ammonium compounds are salts of quaternary ammonium cations. Polyquats are a variety of engineered polymer forms which provide multiple quat molecules within a larger molecule.

<span class="mw-page-title-main">Quaternium-15</span> Salt used as a surfactant

Quaternium-15 is a quaternary ammonium salt that has been used as a surfactant and preservative. It acts as an antimicrobial agent because it slowly releases formaldehyde, which is a preservative with biocidal properties.

Cetyl alcohol, also known as hexadecan-1-ol and palmityl alcohol, is a C-16 fatty alcohol with the formula CH3(CH2)15OH. At room temperature, cetyl alcohol takes the form of a waxy white solid or flakes. The name cetyl derives from the whale oil (cetacea oil, from Latin: cetus, lit. 'whale', from Ancient Greek: κῆτος, romanized: kētos, lit. 'huge fish') from which it was first isolated.

<span class="mw-page-title-main">Hydroxysultaine</span> Class of chemical compounds

Hydroxysultaines are chemical compounds used in high-foaming shampoos, bath products and shower gels especially in conjunction with ether sulfates and alkyl sulfates. They are also used in industrial applications where high, stable foam is required. Chemically, hydroxysultaines are zwitterionic, typically containing covalently linked positive and negative ions.

<span class="mw-page-title-main">Cocamide</span> Chemical compound

Cocamide is a mixture of amides manufactured from the fatty acids obtained from coconut oil. As coconut oil contains about 50% of lauric acid, in formulas only the 12-carbon chains tend to be considered. Therefore the formula of cocamide can be written as CH3(CH2)10CONH2, though the number of carbon atoms in the chains varies.

<span class="mw-page-title-main">Triethanolamine</span> Chemical compound

Triethanolamine, or TEOA, is an organic compound with the chemical formula N(CH2CH2OH)3. It is a colourless, viscous liquid. It is both a tertiary amine and a triol. A triol is a molecule with three alcohol groups. Approximately 150,000 tonnes were produced in 1999. It is a colourless compound although samples may appear yellow because of impurities.

<span class="mw-page-title-main">Allergic contact dermatitis</span> Medical condition

Allergic contact dermatitis (ACD) is a form of contact dermatitis that is the manifestation of an allergic response caused by contact with a substance; the other type being irritant contact dermatitis (ICD).

<span class="mw-page-title-main">Tetrazepam</span> Chemical compound

Tetrazepam is a benzodiazepine derivative with anticonvulsant, anxiolytic, muscle relaxant and slightly hypnotic properties. It was formerly used mainly in Austria, France, Belgium, Germany and Spain to treat muscle spasm, anxiety disorders such as panic attacks, or more rarely to treat depression, premenstrual syndrome or agoraphobia. Tetrazepam has relatively little sedative effect at low doses while still producing useful muscle relaxation and anxiety relief. The Co-ordination Group for Mutual Recognition and Decentralised Procedures-Human endorsed the Pharmacovigilance Risk Assessment Committee (PRAC) recommendation to suspend the marketing authorisations of tetrazepam-containing medicines across the European Union (EU) in April 2013. The European Commission has confirmed the suspension of the marketing authorisations for Tetrazepam in Europe because of cutaneous toxicity, effective from the 1 August 2013.

<span class="mw-page-title-main">Sodium lauroamphoacetate</span> Chemical compound

Sodium lauroamphoacetate is a zwitterionic surfactant of the amphoacetate class. It is used as a very mild cleaning agent originally used in shampoos and body washes for infants but it now sees broader use in other personal care products.

Amidoamines are a class of chemical compounds that are formed from fatty acids and amines. They are used as intermediates in the synthesis of surfactants, such as cocamidopropyl betaine (CAPB), some of which are used in personal care products including soaps, shampoos, and cosmetics. Amidoamines can also serve as curing agents for epoxy resins. They are also used as oil well drilling fluids and also as corrosion inhibitors.

<span class="mw-page-title-main">Dimethylaminopropylamine</span> Chemical compound

Dimethylaminopropylamine (DMAPA) is a diamine used in the preparation of some surfactants, such as cocamidopropyl betaine which is an ingredient in many personal care products including soaps, shampoos, and cosmetics. BASF, a major producer, claims that DMAPA-derivatives do not sting the eyes and makes a fine-bubble foam, making it appropriate in shampoos.

Eyelid dermatitis is commonly related to atopic dermatitis or allergic contact dermatitis. Volatile substances, tosylamide, epoxy hardeners, insect sprays, and lemon peel oil may be implicated, with many cases of eyelid contact dermatitis being caused by substances transferred by the hands to the eyelids.

Allergen of the Year is an annual "award" voted upon by the American Contact Dermatitis Society. The purpose of the award is "to draw attention to the agents causing the most significant clinical effects, those that are underrecognized and those that have become obsolete or for which exposure patterns have changed".

<span class="mw-page-title-main">Cocamidopropyl hydroxysultaine</span> Chemical compound

Cocamidopropyl hydroxysultaine (CAHS) is a synthetic amphoteric surfactant from the hydroxysultaine group. It is found in personal care products. It has uses as a foam booster, viscosity builder, and an antistatic agent.

<span class="mw-page-title-main">Iodopropynyl butylcarbamate</span> Chemical compound

Iodopropynyl Butyl Carbamate (IPBC) is a water-soluble preservative used globally in the paints & coatings, wood preservatives, personal care, and cosmetics industries. IPBC is a member of the carbamate family of biocides. IPBC was invented in the 1970s and has a long history of effective use as an antifungal technology.

<span class="mw-page-title-main">Nickel allergy</span> Medical condition

Nickel allergy is any of several allergic conditions provoked by exposure to the chemical element nickel. Nickel allergy often takes the form of nickel allergic contact dermatitis (Ni-ACD), a form of allergic contact dermatitis (ACD). Ni-ACD typically causes a rash that is red and itchy and that may be bumpy or scaly. The main treatment for it is avoiding contact with nickel-releasing metals, such as inexpensive jewelry. Another form of nickel allergy is a systemic form: systemic nickel allergy syndrome (SNAS) can mimic some of the symptoms of irritable bowel syndrome (IBS) and also has a dermatologic component.

<span class="mw-page-title-main">Lip licker's dermatitis</span> Medical condition

Lip licker's dermatitis is a type of skin inflammation around the lips due to damage by saliva from repetitive lip licking and is classified as a subtype of irritant contact cheilitis. The resulting scaling, redness, chapping, and crusting makes a well-defined ring around the lips. The rash may extend as far as the tongue can reach and usually does not occur at the corners of the mouth. It commonly occurs during winter months but some people can have it year-round if lip licking is a chronic habit.

<span class="mw-page-title-main">Metal allergy</span> Medical condition

Metal allergies inflame the skin after it has been in contact with metal. They are a form of allergic contact dermatitis. They are becoming more common, as of 2021, except in areas with regulatory countermeasures.

References

  1. 1 2 3 4 5 6 7 8 "Cocoamidopropyl-Betaine-CAPB-SDS" (PDF). Acme-Hardesty. Retrieved 26 May 2021.
  2. ↑ 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
  3. ↑ Stephen A. Lawrence (2004). Amines: Synthesis, Properties and Applications. Cambridge University Press. p. 281.
  4. ↑ Reich, Charles (1997). "Hair Cleansers". In Martin M. Rieger; Linda D. Rhein (eds.). Surfactants in Cosmetics. Surfactant Science Series. Vol. 68 (2nd ed.). New York: Marcel Dekker, Inc. p. 359. ISBN   978-0-8247-9805-5 . Retrieved 9 December 2012.
  5. 1 2 De Groot, A. C.; Van Der Walle, H. B.; Weyland, J. W. (1995). "Contact allergy to cocamidopropyl betaine". Contact Dermatitis. 33 (6): 419–422. doi:10.1111/j.1600-0536.1995.tb02078.x. PMID   8706401. S2CID   42960180.
  6. 1 2 Brand, R.; Delaney, T. A. (1998). "Allergic contact dermatitis to cocamidopropylbetaine in hair shampoo". The Australasian Journal of Dermatology. 39 (2): 121–122. doi:10.1111/j.1440-0960.1998.tb01264.x. PMID   9611386. S2CID   9381720.
  7. 1 2 Mowad, C. (2001). "Cocamidopropyl betaine allergy". American Journal of Contact Dermatitis. 12 (4): 223–224. doi:10.1053/ajcd.2001.29549. PMID   11753899.
  8. ↑ Hande, Vrushali; Choudhary, Nilesh; Chakrabarty, Suman; Kumar, Rajnish (2020-12-01). "Morphology and dynamics of self-assembled structures in mixed surfactant systems (SDS + CAPB) in the context of methane hydrate growth". Journal of Molecular Liquids. 319: 114296. doi:10.1016/j.molliq.2020.114296. ISSN   0167-7322. S2CID   224848279.
  9. ↑ Bhattacharjee, Gaurav; Kushwaha, Omkar Singh; Kumar, Asheesh; Khan, Muzammil Yusuf; Patel, Jay Narayan; Kumar, Rajnish (2017-04-05). "Effects of Micellization on Growth Kinetics of Methane Hydrate". Industrial & Engineering Chemistry Research. 56 (13): 3687–3698. doi:10.1021/acs.iecr.7b00328. ISSN   0888-5885.
  10. ↑ Shaffer, K. K.; Jaimes, J. P.; Hordinsky, M. K.; Zielke, G. R.; Warshaw, E. M. (2006). "Allergenicity and cross-reactivity of coconut oil derivatives: A double-blind randomized controlled pilot study". Dermatitis: Contact, Atopic, Occupational, Drug. 17 (2): 71–76. PMID   16956456.
  11. ↑ Fowler Jr, J. F.; Zug, K. M.; Taylor, J. S.; Storrs, F. J.; Sherertz, E. A.; Sasseville, D. A.; Rietschel, R. L.; Pratt, M. D.; Mathias, C. G.; Marks, J. G.; Maibach, H. I.; Fransway, A. F.; Deleo, V. A.; Belsito, D. V. (2004). "Allergy to cocamidopropyl betaine and amidoamine in North America". Dermatitis: Contact, Atopic, Occupational, Drug. 15 (1): 5–6. PMID   15573641.
  12. ↑ Korting, H. C.; Parsch, E. M.; Enders, F.; Przybilla, B. (1992). "Allergic contact dermatitis to cocamidopropyl betaine in shampoo". Journal of the American Academy of Dermatology. 27 (6 Pt 1): 1013–1015. doi:10.1016/S0190-9622(08)80270-8. PMID   1479082.
  13. ↑ Foti, C.; Bonamonte, D.; Mascolo, G.; Corcelli, A.; Lobasso, S.; Rigano, L.; Angelini, G. (2003). "The role of 3-dimethylaminopropylamine and amidoamine in contact allergy to cocamidopropylbetaine". Contact Dermatitis. 48 (4): 194–198. doi:10.1034/j.1600-0536.2003.00078.x. PMID   12786723. S2CID   9944011.
  14. ↑ Fowler, J. F.; Fowler, L. M.; Hunter, J. E. (1997). "Allergy to cocamidopropyl betaine may be due to amidoamine: A patch test and product use test study". Contact Dermatitis. 37 (6): 276–281. doi:10.1111/j.1600-0536.1997.tb02464.x. PMID   9455630. S2CID   7933812.
  15. ↑ History of Allergen of the Year Archived 2014-04-25 at the Wayback Machine . contactderm.org
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