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Sugar chemistry

Creating bio-based ingredients with multiple functions
Seppic Technologies : Sugar Chemestry

Sugar chemistry creates bio-based ingredients for many purposes.

At Seppic, the application of this chemistry is built around a comprehensive knowledge in the field of sugars and the 12 principles of green chemistry. This involves an entire ecosystem, spanning sugar supply chains, understanding of the molecular structures and chemical properties of sugars and their derivatives, processing and analytical methods. It even extends to mastering the functionality and performance of the ingredients, whether foaming, wetting, hydrotope, solubilizing, detergent, emulsifying or biologically active, in the finished products.

Mastering the chemistry of sugars and the chemistry of polyols, has given rise to three main families of nonionic surfactants:

  • Sorbitan esters,
  • Alkyl PolyGlycosides (APG),
  • Polyol PolyGlycosides (PPG).

Origin of sugars

Sugars form a polar raw material of choice for the development of bio-surfactants due to their large number of hydroxyl functions.

A raw material, sugars are typically derived from plant sources such as wheat starch, corn starch, manioc, or potato, and also from hemicellulose from hardwood barks such as birch. Their wide variety of structures includes glucose and xylose, as well as polyol derivatives such as sorbitol or xylitol. Seppic was the first to make a Polyol PolyGlycoside on xylitol base for the cosmetic market.

Sugar processing

The development of ingredients derived from sugar chemistry is sustainable, from the raw materials originating from common plant sources, to the recycling of production by-products, until the end-of-life of biodegradable ingredients.

At Seppic, the development of this technology combined our expertise in sugar reactions with our methods for evaluating the performance of ingredients derived from these reactions. This requires understanding how to choose the right structures to associate with “good sugar” in order to optimize reactivity, control stoichiometry of the reaction, to target the ultimate effectiveness of the ingredient.

Seppic specializes in glycosylation of reducing sugars and esterification of sorbitol. These transformations are carried out without solvents and respect the principles of green chemistry. Depending on the molecules to which the sugars are combined – fatty carboxylic acids or fatty alcohol – they generate different families of nonionic surfactants such as Alkyl Polyglycosides and sorbitan esters. The way a reducing sugar reacts with a polyol makes it also possible to create hydrophilic active ingredients: Polyol Polyglycosides. Sugar chemistry offers a vast array of possibilities!

Green chemistry and sustainable chemistry

Green chemistry is based on 12 principles, published in 1998 (Anastas, PT; Warner, JC Green Chemistry: Theory and Practice, Oxford University Press: New York, 1998), which aim to guide innovation at the molecular level towards safe and environmentally friendly chemical reactions. This concept has evolved towards sustainable chemistry (P. Marion, B. Bernela, A. Piccirilli, B. Estrine, N. Patouillard, J. Guilbot, F. Jérôme. Sustainable chemistry: how to produce better and more from less?, Green Chem., 2017.19, 4973-4989, Royal Society of Chemistry), to which Seppic is fully committed. Sustainable chemistry takes account of the entire value chain from the origin and supply of raw materials, the manufacturing processes, the societal and environmental impacts, to the end-of-life of ingredients.

 

Sorbitan esters, lipophilic emulsifiers

Sorbitan esters are obtained through the esterification of sorbitol in the presence of a suitable catalyst. The complexity of the reaction media must be perfectly controlled in order to obtain ingredients of reproducible composition.

Esterification of sorbitol and carboxylic acid (monoester) Esterification of sorbitol and carboxylic acid (monoester)

Sorbitan esters are lipophilic emulsifiers used in cosmetics and dermopharmacy (Montane™ for example). They are also emulsifiers of choice for drugs administered by parenteral route (Montane™ PPI). 

Alkyl PolyGlycosides, with multiple properties

Alkyl PolyGlycosides (APG) are obtained by glycosylation of a reducing sugar with an excess of molten fatty alcohol. The reaction produces water, which is progressively eliminated, as well as Alkyl PolyGlycosides. Excess fatty alcohol, whether of long or short chain, is either retained or evaporated depending on the properties desired for the final surfactant. At Seppic, the biomass residues generated during the production of emulsifiers (long chain fatty alcohols) are recycled into electricity and natural fertilizers for agriculture by a methanization process.

Glycosylation of glucose by a fatty alcohol Glucose glycosylation by a fatty alcohol

When fatty alcohol contains a long chain of at least 14 carbon atoms, the APG has emulsifying properties (Montanov™ and Fluidanov™ for example). In addition, some of Seppic's APGs, such as Montanov™ 68 and Montanov™ 202, have the structure to create stable liquid crystals within cosmetic emulsion systems. These liquid crystals have a lamellar structure close to that of lipids of the stratum corneum (intercellular lipids of the stratum corneum), and as such, offer restructuring properties by interacting with the lipids of the skin.

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Positive Impact Of Performance Emulsifiers On End-users Skin Benefits

When fatty alcohol contains a shorter chain of less than 14 carbon atoms, the APG is presented in an aqueous solution with solubilizing, hydrotope (Simulsol™ SL 7 G for example), wetting or foaming (Oramix™ for example) properties. These bio-based surfactants are mainly used in cosmetic and dermopharmaceutical formulas (face cleansing gels, shower gels, etc.), or detergents.

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A 100% Bio-based And Sustainable Solubilizer For Water-based Cosmetic Formulas

 

Optimization of the life cycle of Montanov ™ emulsifiers

Plant biomass residues from the Montanov™ emulsifier manufacturing process are recycled locally in farms near their manufacturing site. These residues are mixed with pig manure and then introduced into a digester to produce biogas (methane and CO2) used for electricity production. Non-volatile elements, or compost, are used as a natural fertilizer on the farm. Compared to the conventional process of destruction by incineration, this recycling process initiated in 2017 reduces the equivalent of around 100 tonnes of CO2 emissions per year.

Recycling of plant biomass from the Montanov™ manufacturing process

Recycling of plant biomass from the Montanov™ manufacturing process

 

Polyol PolyGlycosides

Polyol PolyGlycosides are obtained by a glycosylation reaction of a reducing sugar, for example glucose, in the presence of a polyol such as xylitol, the final product being diluted in water.

Glycosylation of glucose with xylitol Glycosylation of glucose with xylitol

Polyol PolyGlycosides are used to create hydrophilic active ingredients. For example, xylitylglucoside is a powerful moisturizing agent that acts on the skin’s surface layers, and more deeply with a restructuring effect (Aquaxyl™). At Seppic, these bio-based active ingredients from the wesource platform represent more than 65 patent families.

Scientific communication
Versatile Performance Of A Sugar-based Moisturizer In Naturally-based Skin Care Formulas