Fatty Amines in Detergents and Cosmetics: Current State and Biocircular Perspectives
Abstract
1. Introduction
2. Fatty Amines Properties and Current State Production
2.1. Fatty Amines Properties
2.2. Fatty Amines Production
2.2.1. Nitrile Process
2.2.2. Amination of Alcohols
2.2.3. Amination of Fatty Compounds and N-Alkylation
3. Fatty Amines in Detergents
3.1. Detergents Formulations
3.1.1. Surfactants
3.1.2. Surfactants and Other Ingredients for Shampoo
- Cuticle: This is the outermost layer of the hair shaft, composed of overlapping, scale-like cells that shield the hair and contribute to its visual qualities, such as shine and smoothness.
- Cortex: Located beneath the cuticle, the cortex houses the pigments responsible for hair color and provides strength and elasticity to the hair strand.
- Medulla: This is the innermost core of the hair, running through the center of the strand. Its presence and structure can vary depending on hair type and thickness.
- Lauryl sulfates: they are used with water (main component) in most shampoos designed to produce good hair cleansing. Examples of lauryl sulfate detergents include: sodium lauryl sulfate (NaC12H25SO4), triethanolamine lauryl sulfate (C18H41NO7S), and ammonium lauryl sulfate (C12H29NO4S). These compounds are popular primary cleansers because they work well in both hard and soft water, are easily rinsed and produce rich foam. Although they are excellent cleansers, they are not delicate on the hair. A secondary detergent and possible use of a conditioning agent are thus necessary. Lauryl sulfates are commonly used in shampoos for oily hair.
- Laureth sulfates: they are the most used primary detergents in general shampoos designed for normal-to-dry hair. Generally, they produce abundant foam. Examples are: triethanolamine laureth sulfate (C12H25(OCH2CH2)3OSO3H·(HOCH2CH2)3N), sodium laureth sulfate (CH3(CH2)10CH2(OCH2CH2)nOSO3Na), and ammonium laureth sulfate (C12H25(OCH2CH2)nOSO3NH4).
- Sulfonates: Sulfonates—particularly alkylbenzene sulfonates—are extensively used as anionic surfactants in a wide range of cleaning products. They efficiently solubilize and remove dirt and oils. This makes them especially suitable for formulations such as soaps, shampoos, and laundry detergents. They are often used in sulfate-free shampoos. Sulfonate aromatic detergents, specifically those containing alkylbenzene sulfonates (ABS), are generally considered problematic due to their non-biodegradability while some sulfonate detergents, like those with linear alkylbenzene sulfonates (LAS), are biodegradable [36].
- Sarcosines: they are generally not used as primary detergents, because they do not effectively remove sebum from the hair. Nevertheless, they are good conditioners, so they are commonly used as the second (or third) detergent listed on labels reporting the shampoo ingredient list. Sarcosines are used in conditioning and dry hair shampoos. Detergents of this class are generally mentioned on the shampoo label as lauryl sarcosine (C15H29NO3) and sodium lauryl sarcosinate (C15H28NO3Na).
- Sulfosuccinates: they represent a class of very effective detergents, suitable in removing sebum from oily hair. Thus, they are commonly used as secondary surfactant in shampoos for oily hair. Examples of this class are sodium dioctyl sulfosuccinate and disodium oleamine sulfosuccinate.
3.2. Fatty Amines and Their Derivatives in Detergents Formulations
3.2.1. Amine Oxide
- Alkyl Dimethyl Amine Oxides (ADAO): These are versatile amine oxides with a range of alkyl chain lengths, typically C10-C16. They are widely used in various detergents due to their excellent cleaning and foaming properties. The interaction of solid alkyl dimethylamine oxide and di-tallow dimethyl ammonium chloride (DTMAC, [(CnH2n+1)2N(CH3)2]Cl) and di-tallow dimethyl ammonium sulfate (DTMAS, [(CnH2n+1)2N(CH3)2]2SO4) quats in different types of fabric softener systems was studied by focusing on their synergistic behavior. Softening, wetting, whiteness retention and static electricity build-up were evaluated for laundry rinses, laundry detergents and dryer sheets. In fabric rinses, combining amine oxide with DTMAC enhanced the wetting of cotton towels due to a synergistic effect. While this synergy was not seen in laundry detergents, formulations with amine oxide still outperformed those with DTMAC alone, offering better cleaning without the blotchy residue often caused by the quaternary salt [41]. Alkyl dimethylamine oxides also showed pronounced antimicrobial activity if used alone or in combination with alkyl betaines [42].
- Coco Amine Oxide: Derived from coconut oil, coco amine oxides are biodegradable and often used in environmentally friendly detergent formulations. They exhibit good surfactant properties and are particularly effective in dishwashing detergents.
- Lauryl Amine Oxide, like C12H25N(CH3)2O Lauryl amine oxides are derived from lauryl alcohol and are commonly used in laundry detergents, household cleaners and foaming agent for skin and hair. They provide excellent cleaning performance and are compatible with other detergent ingredients.
- Behenyl Amine Oxide Behenyl amine oxides, like for instance C22H45N(CH3)2O, are derived from behenic acid and are often used as conditioning agents in hair care products. They provide a soft and silky feel to the hair while also aiding in cleansing.
3.2.2. Ethoxylated Fatty Amines
3.2.3. Quaternary Ammonium Compounds
- Alkyl Dimethyl Benzyl Ammonium Chloride (ADBAC):(CnH2n+1)N(CH3)2CH2PhCl. ADBAC is widely used in disinfectant and detergent formulations for its broad-spectrum antimicrobial activity against bacteria, viruses, and fungi. It is effective in both acidic and alkaline conditions and is commonly found in household disinfectants and industrial cleaners.
- Dodecyl Dimethyl Ammonium Chloride (DDAC): C22H48ClN. DDAC is another quaternary ammonium salt with strong antimicrobial properties. It is commonly used in healthcare facilities, food processing plants, and institutional settings as a disinfectant and sanitizer. It is effective against a wide range of pathogens, including bacteria, viruses, and fungi.
- Benzalkonium Chloride (BAC): PhCH2(CnH2n+1)N(CH3)2Cl. BAC is a versatile quaternary ammonium salt used in various cleaning and disinfecting products, including detergents, hand sanitizers, and surface disinfectants. It is effective against bacteria, viruses, and algae and is commonly used in both commercial and household settings.
- Cetyl Trimethyl Ammonium Chloride (CTAC): C19H42N(CH3)3Cl. CTAC is often used as a surfactant and antistatic agent in fabric softeners, laundry detergents, and hair care products. It helps to reduce static cling and improve the softness and manageability of fabrics and hair.
- Octyl Decyl Dimethyl Ammonium Chloride (ODDAC): C8H17(C10H21)N(CH3)2CL. ODDAC is commonly used as a surfactant and antimicrobial agent in detergents and disinfectants. It has excellent wetting and emulsifying properties and is effective against a wide range of microorganisms.
- A growing body of literature highlights concerns regarding quats build-up and rinsability, particularly in hair care. Cetyl Trimethyl Ammonium Chloride (CTAC) is used in many products and is generally well tolerated at concentrations between 0.5 and 2.5%, although isolated cases of dermatitis have been reported. Cetylpyridinium chloride (CPC), commonly found in oral care products, has a lower incidence of skin reactions and is often used in milder formulations. Cetyl Trimethyl Ammonium bromide (CTAB), while effective, has been linked to keratinocyte proliferation and sensitization in some studies, suggesting caution with prolonged exposure [12].
3.2.4. Fatty Amines in Fabric and Hair Detergents
- 3–8 wt % quaternary ammonium compound dispersions for addition to the rinse cycle.
- Quaternary ammonium compound formulations on nonwoven sheets or polyurethane foam, containing a fatty-acid ester transfer agent, for use in clothes dryers.
- Combined detergent, softener, and antistatic formulations for single-cycle use in washing machines.
4. Fatty Amines in Cosmetics
4.1. Functional Roles in Cosmetic Formulations
4.2. Types of Fatty Amines and Their Uses
4.2.1. Cocamine and Its Derivatives
4.2.2. Soyamine and Dimethyl Soyamine
4.2.3. Myristamine and Myristamine Oxide
4.2.4. Lauramine and Its Derivatives
4.3. Commercial Applications in Cosmetics
5. Fatty Amines and Sustainability
5.1. Alternative Methods of Synthesis
5.1.1. Use of Enzymes
5.1.2. Synthesis in Water
5.1.3. One-Step Vapor-Phase Thermocatalysis of Triglycerides
5.1.4. Aliphatic Amines from Plastic Waste
5.2. A Biocircular Approach
5.2.1. Use of Agro-Food Waste and By-Products as Raw Materials for Synthesizing Fatty Amines
5.2.2. Biotechnological Paths for Fatty Amines
5.2.3. Fatty Amines and Cationic Derivatives as Additives in Biobased Formulations
6. Conclusions
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
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Class of Fatty Amine Derivative | Primary Functions in Hair Detergents | Examples |
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Amine oxide |
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Ethoxylated fatty amines Non-ionic |
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Quaternary ammonium compounds cationic |
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Coltelli, M.-B.; Serpico, A.; Domenech, R.; Tronch, M.; Galli, C.; Sonzini, P.; Escrivà-Cerdán, C.; Mastroianni, S.; Lazzeri, A.; Licursi, D.; et al. Fatty Amines in Detergents and Cosmetics: Current State and Biocircular Perspectives. Cosmetics 2025, 12, 227. https://doi.org/10.3390/cosmetics12050227
Coltelli M-B, Serpico A, Domenech R, Tronch M, Galli C, Sonzini P, Escrivà-Cerdán C, Mastroianni S, Lazzeri A, Licursi D, et al. Fatty Amines in Detergents and Cosmetics: Current State and Biocircular Perspectives. Cosmetics. 2025; 12(5):227. https://doi.org/10.3390/cosmetics12050227
Chicago/Turabian StyleColtelli, Maria-Beatrice, Annabel Serpico, Rosa Domenech, Mar Tronch, Carolina Galli, Paolo Sonzini, Clara Escrivà-Cerdán, Sergio Mastroianni, Andrea Lazzeri, Domenico Licursi, and et al. 2025. "Fatty Amines in Detergents and Cosmetics: Current State and Biocircular Perspectives" Cosmetics 12, no. 5: 227. https://doi.org/10.3390/cosmetics12050227
APA StyleColtelli, M.-B., Serpico, A., Domenech, R., Tronch, M., Galli, C., Sonzini, P., Escrivà-Cerdán, C., Mastroianni, S., Lazzeri, A., Licursi, D., & Raspolli Galletti, A. M. (2025). Fatty Amines in Detergents and Cosmetics: Current State and Biocircular Perspectives. Cosmetics, 12(5), 227. https://doi.org/10.3390/cosmetics12050227