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Diglycerol for Ester Production

Nonionic surfactants are added to a variety of consumer products to perform many functions such as emulsification, wetting, foaming, thickening, dispersion, and solubilization. Although they are much milder than ionic surfactants, they still suffer from many disadvantages. Concerns with ethoxylates range from the possible presence of residual monomers, to degradation during storage, especially in the presence of UV light. They also biodegrade slowly. Other surfactants, such as polysorbate derivatives1, may have limited use on damaged skin. Another concern is the possible presence of toxic nitrosamines in some raw materials. These may be generated during the manufacture of amine oxides, for example, or during storage and use of raw materials if small amounts of unreacted secondary amine impurities are present in the product. These issues led to the increasing use of the more innocuous glycerol and polyglycerol fatty acid esters. Biocompatible and biodegradable, fatty acid esters have overcome many of the concerns listed above.

www.solvayinterox.com 1-800-INTEROX Copyright 2001, Solvay Interox, Inc. All Rights Reserved. Issue date:5/2001 TDS-DGL-01-003 Page 1 of 7

Solvay Interox


Product Data Sheet

10 9 8 7 Solvay Diglycerol (MW=168) Condensation Polyglycerol-2 (MW=168) Abundance (%) 6 5 4 3 2 1 0 Cyclic Branched Solvay Interox. polyglycerol-2 products can have up to 40% glycerol for the same average molecular weight. In contrast. dispersants. Solvay Diglycerol is manufactured by a process that eliminates many of these drawbacks. www. formulators have developed technologies that allow the use of these products in a wide range of industries.com Copyright 2001. (See technical data sheets DGL-01-001 and 002 for detailed information on the properties of Solvay Diglycerol. This enhances the properties of diglycerol esters vs. and cosmetic oils. 100 90 80 70 Solvay Diglycerol (MW=168) Condensation Polyglycerol-2 (MW=168) Abundance (%) 60 50 40 30 20 10 0 Glycerol Diglycerol Triglycerol Tetraglycerol Pentaglycerol Hexaglycerol Glycerol Oligomer q The properties of esters made from Solvay Diglycerol are further enhanced by the low content of cyclic and branched oligomers in the product. and spreading agents. polyglycerol-2 esters. Solvay does not produce diglycerol esters. Inc. All Rights Reserved.) q Solvay Diglycerol has a narrow oligomer distribution.Polyglycerol esters function not only as emulsifiers. but are also used as fragrance carriers. and with the hygienic advantages they offer. Production The polyglycerol moiety in esters is traditionally obtained by alkaline polycondensation of glycerol. as discussed below. emollients.solvayinterox. It contains a minimum of 92% diglycerol and a very small amount of glycerol and triglycerol. Due to the innocuous nature of glycerol and polyglycerol esters. as well as in a variety of technical applications. In contrast. including cosmetics and food. TDS-DGL-01-003 Issue date: 5/2001 Page 2 of 7 . This process tends to reduce the consistency and purity of these products.

diglycerol monostearate) form α-crystal gel phases which remain stable at room temperature. Diglycerol esters are more lipophilic than the corresponding polyglycerol derivatives. For example. s Higher viscosity of the external water phase.g. Being a small hydrophilic molecule.solvayinterox. such as terminal. s Longer formulation shelf life.. This gives diglycerol esters the following advantages: s q Better emulsification properties since ß-crystals have a lower ability to stabilize emulsions. degree of unsaturation. q Position of the hydroxyl groups esterified. q Degree of esterification. 25 no emulsifier propylene glycol C16/C18 monoester Interfacial tension (mN/m) distilled glycerol monostearate 20 Solvay Diglycerol C16/C18 monoester 15 10 5 15 25 35 45 55 65 Time (min) Solvay Interox.1% ester solution in Miglyol® 812N (caprylic-/capric acid triglycerides) and water.com Copyright 2001. Surface activity Diglycerol esters can be used as emulsifiers and thickeners in many applications. www. Inc. They can also exhibit interfacial properties comparable to those of polysorbates5. or vicinal. In addition. a key advantage in food and cosmetic applications. All Rights Reserved. such as chain length. Solvay Diglycerol is guaranteed free from material obtained from animal sources and is Kosher certified. They can be used as primary emulsifiers or co-emulsifiers in W/O or O/W formulations or in multiple emulsions. the corresponding glycerides are polymorphic and transform over time to ß-crystal structures. In some systems. Solvay Diglycerol is also free from material obtained from genetically modified organisms (GMO)2. On the other hand. Due to its high purity. and additional functionalities. The following results were obtained using a 0. leading to enhanced stabilization of O/W emulsions or foams. other polyglycerol or glycerol esters in a variety of applications. diglycerol generates esters that have intermediate properties between glycerol and polyglycerol esters.q q The low variability of Solvay Diglycerol composition allows the production of esters with consistent quality. As emulsifiers. diglycerol esters have a better surface activity than the equivalent glycerol4 and propylene glycol derivatives. TDS-DGL-01-003 Issue date: 5/2001 Page 3 of 7 . diglycerol monododecanoate produces very stable foam and has the same detergency as conventional ether-type nonionics3. Solvay Diglycerol is practically odorless and colorless and generates esters of comparable purity. Properties The properties of diglycerol fatty acid esters depend upon: q Nature of the fatty acid chosen. but more hydrophilic than the equivalent glycerides. The following discussion will focus mainly on the advantages of diglycerol fatty acid esters vs. diglycerol esters offer many advantages. q Gel network structures prepared with diglycerol monoesters (e.

. This eliminates the need to add oil to the formulation. All Rights Reserved.com Copyright 2001. they can be used as skin conditioning emollients in skin care formulations and special lipsticks (for dry lips)8. TDS-DGL-01-003 Issue date: 5/2001 Page 4 of 7 . Due to their high purity.g. These materials can be protected from degradation when solubilized or dispersed in such a fashion (e. Inc. diglycerol esters rinse more easily. however.) Unlike some monoglycerides.g. Unlike other W/O systems. Being more hydrophilic than the corresponding glycerides. i.g. As diglycerol esters exhibit very mild moisturizing properties.q q At high water concentrations (90%). The ability of diglycerol esters to form liquid or liquid crystalline lipid phases gives them unique advantages in solubilizing or dispersing biologically active materials such as peptides and proteins7. Cosmetic applications Like other nonionics. no crystallization at 15°C. esters made from Solvay Diglycerol can be used in transparent personal care formulations. diglycerol monoesters can form multi-lamellar liposomes4. Solvay Interox. the corresponding diglycerol monoesters conform with the general stability requirement of a drug formulation. have unique properties that make them the emulsifiers of choice in many formulations. oleic/linoleic monoesters)7. whereas the corresponding glycerol esters form cubic and reversed hexagonal mesophases in water5 (e. this allows the formation of a hydrophobic “pellicule” on the skin. The following results were obtained using the same system previously described. the monooleate derivatives.) The minimal content of cyclic oligomers in Solvay Diglycerol further enhances the emulsification properties of its esters. This feature is particularly valuable as diglycerol esters are excellent refatting agents in creams and lotions. diglycerol monocaprate. They do.. without leaving a greasy feeling. even with a very high water content. and are of particular interest in “skin sensitive” products. For example. diglycerol monooleate is soluble in water whereas the glycerol derivative is oil soluble6. Due to the generation of stable gel network structures. to allow room temperature storage and use (e. diglycerol esters are milder to the skin than anionic surfactants...e. diglycerol esters are significant viscosity builders in surfactant-based systems.solvayinterox. which therefore rinses off easily without leaving a heavy residue. 25 no emulsifier cyclic diglycerol stearate 20 Interfacial tension (mN/m) 15 Solvay Diglycerol stearate 10 5 0 5 15 25 35 45 55 65 Time (min) The unique properties of diglycerol fatty acid esters discussed above give them several advantages in various applications. www. q q q q q q q q Diglycerol esters such as diglycerol ricinoleate or isostearate make very stable W/O emulsions.

93 g/cm 3 Crumb density: 0.g.41 g/cm 3 Dough density: 0. the corresponding glycerol or polyglycerol esters in many food applications.21 g/cm 3 Crumb density: 0. www. the glycerol derivatives are only stable for a few days due to the greater stability of the diglycerol esters α-crystal gel phases described above. especially in baking. the corresponding glycerides. All Rights Reserved.43 g/cm 3 Crumb density: 0. This is particularly beneficial in baking. and diglycerol esters are authorized for use as food emulsifiers in many countries (see Regulatory Section for details.24 g/cm 3 Solvay Interox.Food applications Emulsifiers are commonly used in many food products.68 g/cm 3 Crumb density: 0.94 g/cm 3 Dough density: 0. Fresh gels made from esters based on Solvay Diglycerol have equivalent performance to those made by corresponding glycerides. Solvay Diglycerol Monostearate No emulsifier Glycerol Monostearate Dough density: 0.solvayinterox. Inc.. TDS-DGL-01-003 Issue date: 5/2001 Page 5 of 7 .42 g/cm 3 Crumb density: 0.) Diglycerol esters have superior properties vs.76 g/cm3 Dough density: 0. On the other hand.23 g/cm 3 Eight week old gels made from esters based on Solvay Diglycerol have superior performance vs.76 g/cm 3 Dough density: 0. diglycerol monostearate) retain their efficacy for several weeks. Glycerol Monostearate Solvay Diglycerol Monostearate No emulsifier Dough density: 0.com Copyright 2001.93 g/cm 3 Crumb density: 0. q Hydrated paste emulsifiers made from diglycerol monoesters (e.

s Good compatibility with other additives (especially important in PVC).22 g/cm 3 Crumb density: 0.27 g/cm 3 q Due to its high purity. s Stabilizing effects against the thermal degradation of PVC. s Good resistance to removal by water. In addition. s Low volatility. Solvay Diglycerol Monostearate Cyclic Diglycerol Monostearate Polyglycerol-2 Monostearate Dough density: 0. their equivalent glycerides. Inc. s Low migration in the polymer. www. The following results were obtained using fresh gels. Diglycerol esters are excellent antifogging/antistatic agents for PVC and polyolefin films. One of their key advantages is their acceptance for food use in many countries.71 g/cm 3 Dough density: 0. Industrial applications Glycerol and polyglycerol esters have been used in a variety of industrial applications for many years. they are highly biodegradable. s Discoloration starts at a high temperature11. Solvay Interox. such as lubrication of food equipment or incorporation in films for food packaging and agriculture.37 g/cm 3 Crumb density: 0. This is of special interest in applications involving food contact. All Rights Reserved.q q Diglycerol esters have superior heat stability vs. diglycerol esters offer the following advantages: s Stability to oxidation10. the corresponding glycerides9.48 g/cm 3 Crumb density: 0. s Higher thermal stability than the corresponding glycerides9.13: s Long lasting antifogging effects. traditional polyglycerol ester products. Derivatization of diglycerol esters offers a larger variety of possibilities vs. The low content of glycerol and cyclic diglycerol oligomers is believed to be the main reason for the better performance of esters made from Solvay Diglycerol vs. q q q As lubricants. condensation polyglycerol-2 esters in baking. due to their following properties12. TDS-DGL-01-003 Issue date: 5/2001 Page 6 of 7 .40 g/cm 3 Dough density: 0. Solvay Diglycerol produces esters that have improved taste vs.com Copyright 2001.solvayinterox.

neither Solvay Interox. PEG-30 Sorbitol Tetraoleate Laurate. Controlled Release Composition. Physical Properties of Diglycerol Esters in Relation to Rheology and Stability of Protein-Stabilized Emulsions. 6 J. 2 At the moment. and M. Solvay Interox. Kuala Lumpur. the information contained herein is accurate as of the date of this document. 1999. Kawada. 10 JP 7173480. Krog. July 9. PEG-60 Sorbitan Tetrastearate. 3 S.A. and K. Pedersen. and -20 Sorbitan Isostearate. PEG-3. PEG-3. PEG-10. Lip Cosmetics Containing Reaction Products of Diglycerin Esters with Dicarboxylic Acids. Inc. TDS-DGL-01-003 Issue date: 5/2001 Page 7 of 7 Solvay Interox a Passion for Progress® DIGLYCEROL Product Data Sheet . and -60 Sorbitan Stearate. and -60 Sorbitan Tetraoleate. However. 43-89 (Report issued by Cosmetic Ingredient Review panel). Berger. A GRAS (Generally Recognized As Safe) notification for esters made from Solvay Diglycerol for these applications is currently under preparation. Final Report on the Safety Assessment of PEG-20 Sorbitan Cocoate. publ. Krog. Anderson (ed. -40. 1957). Inc. 8 JP 7223925. PEG-40 Sorbitan Peroleate. q Japan Diglycerol esters are listed in The Japanese Standards of Cosmetic Ingredients. Jpn. but may be a business of other companies potentially also owning related intellectual property rights. Effect of Monoglycerides and Diglycerol Esters on Viscoelasticity of Heat-Set Whey Protein Emulsion Gels. with regard to the freedom to use any of the information given herein on diglycerol esters. This information is for use by technically skilled persons at their own discretion and risk and does not relate to the use of this product in combination with any other substance or any other process. Inc. No warranty is made and no liability is taken whatsoever by Solvay Interox. in K. 34. 314-320. J.280. publ June 27. Maki. -30. 9 T.Regulatory Status q United States Diglycerol esters are listed in the Dictionary of Cosmetic Ingredients. Polyhydric alcohol fatty acid esters for polymer additives having excellent heat stability. 1971. 383-390. 3333 Richmond Avenue Houston. The latter is a coproduct of biodiesel production obtained by transesterification of rapeseed oil certified from countries where crops of genetically modified rape are forbidden.). 493-501. I. S. 1995 on plastic materials and articles intended to come into contact with foodstuffs. Imparting Antifogging Properties to PVC Resins and Compositions Therefore. Toshima. Phase Behaviour of New Food Emulsifiers and their Application. Malaysia. PEG-40 Sorbitan Perisostearate. Texas 77098 Telephone: 713/525-6500 Or 1-800-INTEROX Fax: 713/524-9032 Website: www. moldability. July 11.com Copyright 2001.854 or for incorporation in polyolefin films under 21 CFR § 177. nor any of its affiliates makes any warranty. 681-692.537.558. and N. 12(3-6). Holstborg. August 22. q European Union Solvay Diglycerol complies with EU polyglycerol specifications for use of polyglycerol esters in food under EU Commission Directive number 98/86/EC (E 475 and E 476) of November 11. Pyrolysis Behaviors and Thermostability of Polyglycerols and Polyglycerol Fatty Acid Esters. PEG-40 and -75 Sorbitan Lanolate. Enzymatic Synthesis. and E. 1995. Olesen. K. 1998.1520.S. References 1 R. Surface Activity. Oils and Fats in Food Applications Proceedings of the Food Applications Session of the 22 nd Congress of the International Society of Fats Research (ISF). PEG-20 and -160 Sorbitan Triisostearate. -40. 2000. Please note that diglycerol esters are not part of the business of Solvay Interox.G. -6. Dickinson. Inc. publ. Antimicrobial Properties and Biodegradability of Diglycerol and Triglycerol Fatty Acid Esters. PEG-40 Sorbitan Diisostearate. July 16.K. and its affiliates. International Journal of Food Science and Technology. A Lubricating Oil Composition which is Safe with Respect to Food. 4 J. PEG-2. or accepts any liability in connection with this information or its use.. 5 S. 1998 on food additives other than colors and sweeteners. Nhya. the glycerol used to make Solvay Diglycerol is either synthetic or biodiesel glycerol. 48(7). publ. All Rights Reserved. 2000. Okada. PEG-80 Sorbitan Palmitate. and have been registered in the list of Food Hygiene Act of Japan under Registration No.solvayinterox. -44. Soc. the manner of use and whether any patents are infringed. Esters made from Solvay Diglycerol are not approved by the US Food and Drug Administration for food use under 21 CFR § 172. in F. Lanigan. T. -75. Safety Assessment of Cosmetic Ingredients. 1991. PEG-20. express or implied. International Journal of Toxicology. 7 WO 98/30206. 1995. and improved odor. Matsumura. Use of Nonionic Surfactants for Preventing the Fogging of Plastic Surfaces and Preparations Containing These Surfactants. -40. January 26. 7-12 September 1997. -5. 1990. Chen. Ushikusa. PEG-40 and -50 Sorbitol Hexaoleate. publ. publ.K. Maruyama.V. The user alone must finally determine suitability of any information or material for any contemplated use. 39(5). PEG-18 Sorbitan Trioleate. 11 JP 2000178229. and -6 Sorbitan Oleate. M. Esters made from Solvay Diglycerol are approved for addition to food-contact materials under EU Directive number 95/3/EC of the European Parliament and Council of Europe of February 23. 13 US 5.Addendum to the Final Report on the Safety Assessment of Polysorbates. 12 US 3. Nihon Yukagakkaishi. Olesen. This is not a license under any patent or other proprietary right. and PEG-60 Sorbitol Tetrastearate . 19(2).and -80 Sorbitan Laurate. Colloids And Surfaces B: Biointerfaces. N.030. B.80 (registration date: July 31. 1999. Diglycerol esters are approved for use as food emulsifiers. To our actual knowledge. Oil Chem. 1999.

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