COCAMIDOPROPYL BETAINE (KOKAMDOPROPL BETAN)
COCAMIDOPROPYL BETAINE
CAS NO: 4292-10-8
SYNONYMS;
Cocamidopropyl betaine; kokoamidpropil betain; Kokoamid Propil Betain; Amphoteric L; Softazoline LP; Obazoline CAB; Amphitol 20AB; Anpholex LB 2; Rewoteric AMB 12; Tego-Betain L 90; 4292-10-8; Lauroylamide propylbetaine; 3-Lauroylamidopropyl betaine; UNII-23D6XVI233; Dimethyl(lauramidopropyl)betaine; Lauroylaminopropyldimethylaminoacetate; N-Laurylamidopropyl-N,N-dimethylbetaine2-[3-(DODECANOYLAMINO)PROPYL-DIMETHYL-AMMONIO]ACETATE; Cocoamidopropyl betaine; 65277-51-2; 1-Propanaminium; N-(carboxymethyl)-N,N-dimethyl-3-[(1-oxododecyl)amino]-; inner salt; 1-Propanaminium; N-(carboxymethyl)-N,N-dimethyl- 3-[(1-oxododecyl)amino]-; hydroxide; inner salt; (3-(Lauroylamino)propyl)dimethylaminoacetic acid; [3-(Lauroylamino)propyl]dimethylaminoacetic acid; Amphosol LB; Obazoline LAB; Empigen BR; Lexaine LM; Monateric LMAB; 1-Propanaminium; N-(carboxymethyl)-N,N-dimethyl-3-((1-oxododecyl)amino)-; Mackam LMB; Softazoline LPB-R; Enagicol L 30B; Dehyton L 12; Rikabion B 300; Lauroylamidopropylbetaine; Lebon 2000L; AC1L2FXAC1Q22BQ; SCHEMBL22684; DTXSID4041282; CTK5C248; NSC8191; MolPort-023-220-314; (3-Lauramidopropyl)dimethylbetaine; 23D6XVI233; C19H38N2O3; NSC 8191; NSC-8191; EINECS 224-292-6; (3-Laurylaminopropyl)dimethylaminoacetic acid; hydroxide,inner salt; 61789-40-0; AN-20275; I427; LP010942; N,N-Dimethyl-N-dodecanoylaminopropylbetaine; Glycine; (3-lauramidopropyl)dimethylbetaine; FT-0670746; 2-[(3-Dodecanamidopropyl)dimethylaminio]acetate; N-(Dodecylamidopropyl)-N,N-dimethylammonium betaine; W-105096; 2-[3-(dodecanoylamino)propyl-dimethylazaniumyl]acetate; (3-Laurylaminopropyl)dimethylaminoacetic acid; UNII-5OCF3O11KX; MRUAUOIMASANKQ-UHFFFAOYSA-N; (Carboxymethyl)(3-lauramidopropyl)dimethylammonium Hydroxide Inner Salt,1-Propanaminium,N-dimethyl-3-[(1-oxododecyl)amino]-, hydroxide, inner salt; Ammonium (carboxymethyl)(3-lauramidopropyl)dimethyl-, hydroxide, inner salt; N-(Carboxymethyl)-N,N-dimethyl-3-[(1-oxododecyl)amino]-1-propanaminium Hydroxide Inner Salt; 1-Propanaminium, N-(carboxymethyl)-N,N-dimethyl-3-((1-oxododecyl)amino)-hydroxide,inner salt; 5437-10-5; N-(Carboxymethyl)-N,N-dimethyl-3-((1-oxododecyl)amino)-1-propanam- inium hydroxide, inner salt; cocamidopropyl betaine; cocamidopropylbetaine; KOKOAMDOPROPL BETAN; KOKOAMIDOPROPIL BETAIN; KOKAMDPROPL BETAN; KOKAMIDPROPIL BETAIN
What You Need to Know about Cocamidopropyl Betaine in Personal Care Products
Cocamidopropyl betaine (CAPB) is a chemical compound found in many personal care and household cleaning products. CAPB is a surfactant, which means that it interacts with water, making the molecules slippery so they don`t stick together.
When water molecules don`t stick together, they are more likely to bond with dirt and oil so when you rinse away the cleaning product, the dirt rinses away, too. In some products, CAPB is the ingredient that makes lather.
Cocamidopropyl betaine is a synthetic fatty acid made from coconuts, so products that are considered “natural” can contain this chemical. Still, some products with this ingredient may cause unpleasant side effects.
Cocamidopropyl betaine allergic reaction
Some people have an allergic reaction when they use products containing CAPB. In 2004, the American Contact Dermatitis Society declared CAPB the “Allergen of the Year.”
Since then, a 2012 scientific review of studies found that it`s not the CAPB itself that causes an allergic reaction, but two impurities that are produced in the manufacturing process.
The two irritants are aminoamide (AA) and 3-dimethylaminopropylamine (DMAPA). In multiple studies, when people were exposed to CAPB that did not contain these two impurities, they did not have an allergic reaction. Higher grades of CAPB that have been purified don`t contain AA and DMAPA and don`t cause allergic sensitivities.
Skin discomfort
If your skin is sensitive to products that contain CAPB, you may notice tightness, redness, or itchiness after you use the product. This kind of reaction is known as contact dermatitis. If the dermatitis is severe, you may have blisters or sores where the product came into contact with your skin.
Most of the time, an allergic skin reaction like this will heal on its own, or when you stop using the irritating product or use an over-the-counter hydrocortisone cream.
If the rash doesn`t get better in a few days, or if it is located near your eyes or mouth, see a doctor.
Eye irritation
CAPB is in several products intended for use in your eyes, like contact solutions, or it`s in products that may run into your eyes as you shower. If you are sensitive to the impurities in CAPB, your eyes or eyelids could experience:
pain, redness, itchiness, swelling
If rinsing the product away does not take care of the irritation, you may want to see a doctor.
Products with cocamidopropyl betaine
CAPB can be found in facial, body, and hair products like: shampoos, conditioners, makeup removers,liquid soaps,body wash,shaving cream,contact lens solutions,gynecological or anal wipes,some toothpastes
CAPB is also a common ingredient in household spray cleaners and cleaning or disinfecting wipes.How to tell if a product has cocamidopropyl betaine
CAPB will be listed on the ingredient label. The Environmental Working Group lists alternative names for CAPB, including:1-propanaminium hydroxide inner salt
In cleaning products, you may see CAPB listed as:
CADG, cocamidopropyl dimethyl glycine, disodium cocoamphodipropionate
The National Institute of Health maintains a Household Product Database where you can check to see if a product you use may contain CAPB.Cocamidopropyl betaine (CAPB) and coconut diethanolamide (CDEA), which are manufactured from coconut oil, are widely used as chemical substances with surfactant property in shampoo, liquid soap and skin cleaners. Allergic contact dermatitis (ACD) may occur against these substances, especially cocamidopropyl betaine. ACD developing against these two substances is rarely seen in the literature. Here we reported a case of ACD caused by CABP and CDEA which admitted with complaints of redness,peeling and cracking of hands.
Occupational allergic contact dermatitis due to cocamidopropyl betaine and coconut diethanolamide
Mahmut Doru, Handan Duman, Tayfur Gini, Serap Özmen, lknur Bostanc
Dr. Sami Ulus Research And Training Hospital Of Women
Cocamidopropyl betaine (CAPB) and coconut diethanolamide (CDEA), which are manufactured from coconut oil, are widely used as chemical substances with surfactant property in shampoo, liquid soap and skin cleaners. Allergic contact dermatitis (ACD) may occur against these substances, especially cocamidopropyl betaine. ACD developing against these two substances is rarely seen in the literature. Here we reported a case of ACD caused by CABP and CDEA which admitted with complaints of redness,peeling and cracking of hands.
Concern Reference
Violation of industry recommendations – Restricted in cosmetics; use, concentration, or manufacturing restrictions – Unsafe in products left on skin and not rinsed off Cosmetic Ingredient Review Assessments
Recommended restricted in cosmetics – use, concentration, or manufacturing restrictions – any Cosmetics Ingredient Review (CIR) 2010. Tentative Report: Cocamidopropyl Betaine and Related Amidopropyl Betains as used in Cosmetics. Pink Book 4, August 30-31, 2010.
Determined safe for use in cosmetics, subject to concentration or use limitations – Safe for use in cosmetics with some qualifications Cosmetic Ingredient Review Assessments
Cocamidopropyl betaine.
Abstract
Cocamidopropyl betaine (CAPB) is an amphoteric synthetic detergent that has been increasingly used in cosmetics and personal hygiene products (eg, shampoos, contact lens solutions, toothpaste detergents, makeup removers, bath gels, skin care products, cleansers, liquid soaps, antiseptics, and gynecologic and anal hygiene products) because it induces relatively mild skin irritation. Delayed T-cell-mediated type IV hypersensitivity reactions to CAPB have been reported, and contact sensitization prevalence is estimated at between 3.0 and 7.2%. The increasing rates of sensitization led to CAPB`s being named Allergen of the Year in 2004. Related impurities rendered during the manufacturing process (such as amidoamine and dimethylaminopropylamine) are thought to play a role in sensitization.
Names
IUPAC name
{[3-(Dodecanoylamino)propyl](dimethyl)ammonio}acetate
Other names
2-[(3-Dodecanamidopropyl)dimethylaminio]acetate
Identifiers
CAS Number:61789-40-0
ECHA InfoCard:100.057.308
EC Number:263-058-8
PubChem CID:20280
Properties:
Chemical formula:C19H38N2O3
Molar mass:342.524 g·mol-1
Cocamidopropyl betaine (CAPB) is a mixture of closely related organic compounds derived from coconut oil and dimethylaminopropylamine.[1] CAPB is available as a viscous pale yellow solution and it 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
Despite the name cocamidopropyl betaine 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).[2]
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.
Specifications and properties
Cocamidopropyl betaine is used as a foam booster in shampoos.[3] 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.[4][5][6]
CAPB is obtained as an aqueous solution in concentrations of about 30%.
Typical impurities of leading manufacturers today:
Sodium monochloroacetate < 5 ppm
Amidoamine (AA) < 0.3%
Dimethylaminopropylamine (DMAPA) < 15 ppm
Glycerol < 3%
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.
Safety
CAPB has been claimed to cause allergic reactions in some users,[4][5][6] but a controlled pilot study has found that these cases may represent irritant reactions rather than true allergic reactions.[7] 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.[8][9] Other studies have concluded that most apparent allergic reactions to CAPB are more likely due to amidoamine.[10][11] Cocamidopropyl betaine was voted 2004 Allergen of the Year by the American Contact Dermatitis Society.[12]
Cocamidopropyl betaine, hindistancevizi ya ve dimetilaminopropilaminden türetilen yakndan ilikili organik bileiklerin bir karmdr. CAPB viskoz soluk sar bir çözelti halinde bulunur ve kiisel bakm ürünlerinde sürfaktan olarak kullanlr.
KOKAMDOPROPL BETAN
HAMMADDE BLGLER
CAS NUMARASI: 61789 – 40 – 0 + 7647 – 14 – 5
KMYASAL YAPISI : YÜZEY AKTF
ETKEN KATEGOR : AMFOTERK
TCAR SM : COCAMDOPROPYL BETANE
ANALZ BLGLER
KMYASAL FORMÜLÜ : KARIIM
MOLEKÜL AIRLII : KARIIM
KAYNAMA NOKTASI ( C ): 100
PH ARALII : 5 – 7
ERME NOKTASI ( C ): 17.5
YOUNLUK : 1.010 GR / CM3
ÇÖZÜNÜRLÜK : SUDA RAHAT ÇÖZÜNÜR.
FZKSEL ÖZELLKLER VE KULLANILDII ALANLAR
FZKSEL GÖRÜNÜMÜ : SIVI
RENK : EFFAF
KOKU : KARAKTERSTK BR KOKUSU VAR.
TEHLKE CLDE VE GÖZ TEMASINDA BOL SU VE SABUN LE YIKAYINIZ. SOLUMA VEYA YUTMA DURUMUNDA EN YAKIN SALIK KURULUUNA BAVURUNUZ.
DEPOLAMA : SERN VE KURU YERDE MUHAFAZA EDLMELDR.
Cocamidopropyl betaine CAPB olarak adlandrlan bileenlerinin bir ksmdrlar.Deterjan endüstrisinde geni kullanmlar vardr. Bu maddeler Amidopropil betaine bal olan çeitli yal asitlerin bileenlerinden diller.Cocamidopropyl betaine , Laramide Propyl Betaine ve Amidopropil betaine genellikle surfaktan olarak kozmetik ve kiisel bakm ürünlerinde +kullanlrlar. Surfaktanlar, su, ya ve kiri Kartra bildiklerinden dolay cilt ve saç temizlenmesine yardmc olurlar. Bu bakmdan bu balamda deterjan katk maddeleri( sabun) gibi davranrlar ve banyo ürünleri, cilt temizleyici ürünler, ampuan gibi saç bakm ürünleri, havadaki kötü koku gidericiler ve spreylerde bulunurlar. Ayrca kokoamidpropil betain ev temizleyici ürünlerinde ( Örnein ,deterjanlar ve el ykama deterjanlar) da kullanlrlar.
Bu materyallerde bildirilen dier ilevler:
-antistatik etkiler
– Koku giderici
– cilt temizleyici
– temizleyici
– çeitli sürfaktanlar
– köpük güçlendirici
– viskozite artrc
– nem ve su artrc
Bilimsel istatistikler:
bu maddeler Dimethylamino propilamine (DMAPA) ve Aminopropyl yal asit ( Dimetilami n “amidamin”) adl iki üretilen üründe bulunurlar.DMAPA ve Amidamin cilde alerjendirler. Bu nedenle üreticiler CAPB ve Loramidopropil betaine üretiminde DMAPA , Amidamin seviyesini, tutarl kalite ve üretim kontrolü yaparak, mümkün olduu kadar düük tutmaya gayret gösterirler. Aktif Coco betaine (Cocomido propil betaine) 30% Hindistan cevizi yalarndan dr. Coco betaine (Cocomido propil betaine) 30% ampuan, banyo köpükleri be el yapm sv sabunlar da ikinci yüzey surfaktanlar ve pürüzsüzlük hissi yaratan maddeler olarak bulunurlar. Coco betaine (Cocomido propil betaine) 30% iyi bir köpük, köpük svs stabilizatörü ve mükemmel slatc özelliklerine sahiptir. ampuanlarda yumuatc olarak kullanlmakta olan Iran Coco betaine (Cocomido propil betaine) 30% ‘ü öneriyoruz. kaliteli hindistan cevizi ya ve kimyasallarn reaksiyonu sonucunda elde edilen en kaliteli CAPB sunmaktayz. Iran Coco betaine (Cocomido propil betaine) 30%`ü banyo ürünleri, ampuan, sabun ve kozmetiklerde surfaktan olarak kullanlr.
Betaine Iran`daki en seçkin (Cocomido propil betaine) üreticilerden biri olarak bilinir.Cocamidopropyl betaine (CAPB) ve coconut dietanolamid; hindistan cevizi yandan elde edilen, sürfaktan özelliinde olup ampuan, sv sabun ve cilt temizleyicilerinde yaygn olarak kullanlan kimyasal maddelerdir. Bu maddelerden özellikle CAPB`e kar allerjik kontakt dermatit (AKD) geliebilmektedir. ki maddeye kar gelien AKD olgusu literatürde az sayda bulunmaktadr. Burada ellerde kzarklk, soyulma, çatlama ikayetleri ile bavuran ve cocamidopropil betaine ve coconut dietanolamid bal allerjik kontakt dermatit tans konulan olgu sunulmutur.Cocamidopropyl betaine (CAPB) ve coconut dietanolamid; hindistan cevizi yandan elde edilen, sürfaktan özelliinde olup ampuan, sv sabun ve cilt temizleyicilerinde yaygn olarak kullanlan kimyasal maddelerdir. Bu maddelerden özellikle kokoamidpropil betain`e kar allerjik kontakt dermatit (AKD) geliebilmektedir. ki maddeye kar gelien AKD olgusu literatürde az sayda bulunmaktadr. Burada ellerde kzarklk, soyulma, çatlama ikayetleri ile bavuran ve cocamidopropil betaine ve coconut dietanolamid bal allerjik kontakt dermatit tans konulan olgu sunulmutur.
IUPAC ad
{[3- (dodekanoilamino) propil] (dimetil) amonyum} asetat
Dier isimler
2 – [(3-Dodecanamidopropyl) dimethylaminio] asetat
Tanmlayclar
CAS Numaras: 61789-40-0
ECHA Bilgi Kart: 100.057.308
EC Numaras: 263-058-8
PubChem CID: 20280
Özellikleri:
Kimyasal formül: C19H38N2O3
Molar kütle: 342.524 g · mol – 1
Cocamidopropyl betaine (CAPB) 1970 ylndan beri
kozmetik ve kiisel hijyen ürünleri içinde kullanlmaktadr
(1). Cocamidopropyl betaine amfoterik, sentetik bir
deterjan olup, kozmetik ve kiisel hijyen ürünleri
olan; ampuan, kontakt lens solüsyonlar, di macunu,
deterjanlar, makyaj temizleyiciler, du jelleri, cilt bakm
ürünleri, temizleyiciler, sv sabunlar, antiseptiklerde bulunur (2). CAPB
içerikli ürünler giderek art göstermitir; 1980 ylnda
kaytl 19.000 kozmetik ürünün 47 tanesi CAPB içerirken,
2005 ylnda 22.016 ürünün 1242 tanesinin CAPB içerdii
bildirilmitir (3-5). 1995-2001 yllar arasnda en fazla
pozitiflik saptanan 50 allerjen arasnda 23. srada yer
almtr ve allerjik kontakt dermatit (AKD) gelitirme
prevelans %3-7.2 arasnda bildirilmitir (3,4,6,7). CAPB’e
kar allerjik kontakt dermatit ilk kez 1983 ylnda
yaynlanmtr.
Kokamidopropil betain (CAPB), hindistancevizi ya ve dimetilaminopropilaminden türetilen yakndan ilikili organik bileiklerin bir karmdr. [1] CAPB viskoz açk sar bir çözelti olarak mevcuttur ve kiisel bakm ürünlerinde sürfaktan olarak kullanlr. Ad, molekülün büyük ksmnn, laurik asit grubu, hindistancevizi yandan türetildiini yanstr. Kokamidopropil betain önemli ölçüde kokamid DEA’nn yerini almtr.
Üretim
Adna ramen kokamidopropil betain betainden sentezlenmez. Bunun yerine, dimetilaminopropilaminin (DMAPA) hindistancevizi veya hurma çekirdei yandan (laurik asit veya metil esteri) ya asitleri ile reaksiyonu ile balayarak iki aamal bir ekilde üretilir. DMAPA’daki birincil amin, üçüncül aminden daha reaktiftir ve bir amit oluturmak için seçici ilavesine yol açar. kinci aamada, kloroasetik asit geri kalan üçüncül amin ile reaksiyona girerek bir kuaterner amonyum merkezi oluturur (bir kuaternizasyon reaksiyonu). [2]
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
Kimya
CAPB, bir ucunda uzun bir hidrokarbon zinciri ve dier ucunda bir polar grup içeren bir ya asidi amididir. Bu, CAPB’nin bir yüzey aktif madde ve bir deterjan görevi görmesini salar. Hem kuaterner amonyum katyonu hem de bir karboksilattan oluan bir zvitteryondur.
Özellikler
Cocamidopropyl betaine ampuanlarda köpük güçlendirici olarak kullanlr. [3] El sabunu gibi banyo ürünlerinde de kullanlan orta kuvvette bir yüzey aktif maddedir. Ayrca kozmetikte bir emülsifiye edici madde ve kvam arttrc olarak kullanlr ve tahrii azaltmak için sadece iyonik yüzey aktif maddeler neden olur. Ayn zamanda Cocamidopropyl betaine, cilt veya mukoza zarlarn tahri etmeyen saç kremlerinde antistatik bir ajan olarak hizmet eder. Bununla birlikte, baz çalmalar bunun bir alerjen olduunu göstermektedir. [4] [5] [6]
CAPB yaklak% 30’luk konsantrasyonlarda sulu bir çözelti halinde elde edilir.
Bugün önde gelen üreticilerin tipik safszlklar:
Sodyum monokloroasetat <5 ppm
Amidoamin (AA) <% 0.3
Dimetilaminopropilamin (DMAPA) <15 ppm
Gliserol <% 3
AA ve DMAPA safszlklar en hassas olandr, çünkü cilt hassaslatrma reaksiyonlarndan sorumlu olduklar gösterilmitir. Bu yan ürünler, orta derecede fazla kloroasetat ve betainizasyon reaksiyonu srasnda pH deerinin tam olarak ayarlanmas ve düzenli analitik kontrol ile önlenebilir.
Emniyet
CAPB’nin baz kullanclarda alerjik reaksiyonlara neden olduu iddia edilmitir, [4] [5] [6] ancak kontrollü bir pilot çalma, bu vakalarn gerçek alerjik reaksiyonlardan ziyade tahri edici reaksiyonlar temsil edebileceini bulmutur. [7] Ayrca, insan çalmalarnn sonuçlar, amidoamin (AA) ve dimetilaminopropilamin (DMAPA) ile safszlklarn düük ve sk bir ekilde kontrol edilmesi durumunda CAPB’nin düük duyarllk potansiyeline sahip olduunu göstermitir. [8] [9] Dier çalmalar, CAPB’ye en belirgin alerjik reaksiyonlarn amidoamin nedeniyle daha olas olduu sonucuna varmtr. Kokamidopropil betain, Amerikan Kontakt Dermatit Dernei tarafndan 2004 Yln Alerjeni seçildi
Nom IUPAC
{[3- (Dodécanoylamino) propyl] (diméthyl) ammonio} acétate
Autres noms
2 – [(3-Dodecanamidopropyl) dimethylaminio] acetate
Identifiants
Numéro CAS: 61789-40-0
Carte Info ECHA: 100.057.308
Numéro CE: 263-058-8
PubChem CID: 20280
Propriétés:
Formule chimique: C19H38N2O3
Masse molaire: 342,524 g · mol – 1
La cocamidopropyl bétaïne (CAPB) est un mélange de composés organiques étroitement apparentés dérivés de l’huile de coco et de la diméthylaminopropylamine. [1] CAPB est disponible sous forme de solution visqueuse jaune pâle et il est utilisé comme surfactant dans les produits de soins personnels. Le nom reflète que la majeure partie de la molécule, le groupe acide laurique, est dérivée de l’huile de coco. La cocamidopropyl bétaïne a remplacé dans une large mesure le cocamide DEA.
Contenu
1 Production
2 Chimie
3 Spécifications et propriétés
4 Sécurité
Production
Malgré le nom, la cocamidopropyl bétaïne n’est pas synthétisée à partir de la bétaïne. Au lieu de cela, il est produit en deux étapes, en commençant par la réaction de la diméthylaminopropylamine (DMAPA) avec les acides gras de l’huile de noix de coco ou de palmiste (l’acide laurique ou son ester méthylique est le principal constituant). L’aminé primaire dans le DMAPA est plus réactive que l’amine tertiaire, ce qui conduit à son addition sélective pour former un amide. Dans la deuxième étape, l’acide chloroacétique réagit avec l’amine tertiaire restante pour former un centre d’ammonium quaternaire (une réaction de quaternisation). [2]
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
Chimie
Le CAPB est un amide d’acide gras contenant une longue chaîne hydrocarbonée à une extrémité et un groupe polaire à l’autre. Cela permet au CAPB d’agir comme surfactant et comme détergent. Il s’agit d’un zwitterion, composé à la fois d’un cation ammonium quaternaire et d’un carboxylate.
Spécifications et propriétés
La cocamidopropyl bétaïne est utilisée comme rappel de mousse dans les shampooings. [3] C’est un tensioactif de force moyenne également utilisé dans les produits pour le bain comme les savons pour les mains. Il est également utilisé en cosmétique comme agent émulsifiant et épaississant, et pour réduire l’irritation que provoqueraient les surfactants purement ioniques. Il sert également d’agent antistatique dans les revitalisants capillaires, qui le plus souvent n’irrite pas la peau ou les muqueuses. Cependant, certaines études indiquent qu’il s’agit d’un allergène. [4] [5] [6]
Le CAPB est obtenu sous forme de solution aqueuse à des concentrations d’environ 30%.
Impuretés typiques des principaux fabricants d’aujourd’hui:
Monochloroacétate de sodium <5 ppm
Amidoamine (AA) <0,3%
Diméthylaminopropylamine (DMAPA) <15 ppm
Glycérol <3%
Les impuretés AA et DMAPA sont les plus critiques, car elles se sont révélées responsables des réactions de sensibilisation cutanée. Ces sous-produits peuvent être évités par un excès de chloroacétate modéré et l’ajustement exact de la valeur du pH pendant la réaction de bétaïnisation accompagné d’un contrôle analytique régulier.
sécurité
Le CAPB aurait provoqué des réactions allergiques chez certains utilisateurs [4] [5] [6], mais une étude pilote contrôlée a révélé que ces cas peuvent représenter des réactions irritantes plutôt que de véritables réactions allergiques [7]. De plus, les résultats d’études sur l’homme ont montré que le CAPB a un faible potentiel de sensibilisation si les impuretés contenant de l’amidoamine (AA) et de la diméthylaminopropylamine (DMAPA) sont faibles et étroitement contrôlées. [8] [9] D’autres études ont conclu que la plupart des réactions allergiques apparentes au CAPB sont plus susceptibles d’être dues à l’amidoamine. [10] [11] La cocamidopropyl bétaïne a été élue allergène de l’année 2004 par l’American Contact Dermatitis Society. [12]