Formulating for Performance While Minimizing Irritation

Formulating for Performance While Minimizing Irritation
Mild Surfactants Formulating for Performance While Minimizing Irritation Nexeo Solutions

Agenda Introduction to Elé Corporation Surfactant Chemistry
Surfactants Types Examples PEL-ALC CA-205P (nonionic) PEL-SULF PEG-12D (anionic) PEL-QUAT SL-5 (cationic) PEL-AMPH ALP (amphoteric) Will introduce Elé Corporation. Briefly review the types of surfactants based on ionic charge and typical characteristics. Share specific product examples from Elé’s surfactant line and how to formulate with them to minimize irritation in your finished product.

Manufacturing near Chicago Since 1945
Ability to manufacture 1000 kg to 40 metric tons Alkoxylation Polymerization Ethoxylation Neutralization Propoxylation Quaternization Amidification Saponification Aminomethylation and other Mannich reactions Esterification Hydrosilylation Elé Corporation was founded in 1945 near Midway airport in Chicago. We service many industries such as polyurethane (silicone surfactants & catalysts), metalworking, ag, and personal care. We got our start in Personal Care around the time Rhodia (now Solvay) purchased MacIntyre Group. Elé’s VP of R&D, lead synthesis chemist and production manager all came from MacIntyre. If “Mac” is in the name – likely they invented it and know how to make it. Guess you can say we have “MacIntyre Know-how”. Elé manufactures all our products through a variety of processes. We are skilled at alkoxylation and making silicone polyethers. Elé is uniquely positioned to support our customers from inception, thru scale up to full production. A large number of varied sized reactors allow us to cost effectively make from very small MOQs all the way up to bulk. In addition, we have the ability to tailor products to meet customer needs. We are able and agile.

What is a Surfactant? The term surfactant is an acronym for surface active agent. Surfactants contain a hydrophilic (water-loving) head group and a hydrophobic tail group. Surfactants are substances that are attracted to surfaces (interfaces) and lower the interfacial tension between the phases.

What do surfactants do? Emulsifying Dispersing / Solubilizing Foaming
Detergency/Cleaning Conditioning Wetting Thickening

Surfactants in solution
Individual molecules are in the bulk solution and on the surfaces CMC => concentration above which micelles form Micelles act as a reservoir of surfactant molecules The hydrophobic tails of the surfactant molecules want out of the water so migrate to any surface – whether air/water, water/solid, or water/oil. After the surfaces are ‘covered’ so to speak with surfactant, if the concentration is high enough, the surfactant forms spherical groups called micelles, with the surfactant tails in the center of the spheres. This is the CMC – Critical Micelle Concentration. The individual surfactant molecules in the bulk solution can switch places with the surfactant on the surfaces or in the micelles and form an equilibrium with them. Micelles can act as a reservoir of surfactant molecules – if the concentration of surfactant swimming around as individual molecules begins to drop, they are replaced by molecules from the micelles.

How surfactants clean Insoluble oils and are attached to solid surfaces and don’t dissolve in water due to their hydrophobicity An insoluble grease or oil, like the surfactant tails, does not want to be in the water

How surfactants clean Hydrophobic surfactant tails are attracted to oil/water interface

How surfactants clean Oil is solubilized and displaced from surfaces
Surfactants keep oil dispersed in solution

Surfactant Irritation
Surfactants can also solubilize natural skin lipids Denature skin proteins Result is irritation and inflammation Sometime surfactants can work too well Thus the need for mild surfactants in personal care products

Surfactant Types Type Subtypes - Attributes Nonionic Anionic Cationic
Alkoxylates (PEGs, PPGs, PEG/PPG copolymers) - Hydrogen bonding provides water solubility Alkanolamides (DEA, DIPA, MIPA, etc.) - Used for emulsification, thickening, foam stabilization, generally low irritation and toxicity Alkyl Glucosides (Decyl, Lauryl, Coco) - Mainly used for emulsification, thickening, and other functions Anionic Sulfates, Sulfonates, Carboxylates, Sulfosuccinates, Phosphates, Glutamates Taurates, Isethionates, etc. Negatively charged head, relatively harsh, excellent foamers/detergents Cationic Quaternary ammonium (Benzyl chloride quats, DES quats, etc.) Amine salts (Lactates, propionates) Amines (Alkyl dimethyl amines) Positively charged head, relatively harsh, typically used as conditioners or preservatives, Not all are compatible with anionic surfactants Amphoteric Amphoacetates, Amphopropionates, Amino/iminopropionates, Betaines, Hydroxysultaines Both positive & negative head charges, relatively mild, typically used as secondary surfactants, good foaming, compatible with most other PC ingredients Surfactants are categorized based on the charge (or lack thereof) of their polar headgroup: nonionic, anionic (-), cationic (+), and amphoteric (+/-). Elé makes a wide range of nonionic alkoxylates and alkanolamides. Anionic sulfosuccinates and phosphates. Cationic ammonium chloride quats. Varied amphoterics: amphoacetates, amphopropionates, and hydroxysultaines. Manufactured by Elé

Surfactant Selection Surfactants vary widely in their irritation potential. Surfactant Irritation Profile by Charge/Type Nonionic < Amphoteric < Anionic / Cationic However: there are mild choices in each category Careful surfactant choice allows mild formulations without compromising performance Surfactants vary widely in their irritation potential. Nonionic (0) are the least irritating, then amphoteric surfactants (+/-). Anionic (-) and Cationic (+) are the most irritating. Nonionics like the PEL-ALC line, contain: Ethylene Oxide/EO or Polyethelyene Glycol/PEGs and/or Propylene Oxide/PO or polypropylene glycol/PPG The more EO/PO, the more mild the surfactant. If looking to move away from PEGs, Amphoterics are a logical mild surfactant choice

Alkoxylates (nonionic)
As the amount of EO (PEG) increases: Hydrophilicity increases Water solubility increases HLB increases Mildness increases As the amount of PO (PPG) increases: Some thing to keep in mind about alkoxylates… PO has much less effect on water solubility, etc. But can effect the melting point of products and their interactions in solutions, depending on how it’s incorporated in the polymer. e.g., if interspersed with EO, can make a normally solid product a liquid.

Hydrophilic-Lipophilic Balance
HLB Values of selected PEL-ALC products This chart shows the HLB (hydrophobic - lipofobic balance) values of a sampling of the alcohol alkoxylates made by Elé. The first letters indicate the alcohol and the number after indicates the number of moles of EO. OA – oleth LA – laureth OD – octyldodeceth CSA – ceteareth CA - Ceteth By changing the starting alcohol and the amount of EO, you can go anywhere from a low to a very high HLB. On the right side of the chart you can see the different functions that surfactants of different HLBs perform. …

PEL-ALC CA-205P INCI Name: PPG-5-Ceteth-20 Structure:
Here is an example of a product with both EO & PO. Cetyl alcohol with 20 moles EO and 5 moles PO. Idealized structure shown - PO not actually on end- PO/EO/PO/EO – it is dispersed through out the alcohol chain By breaking up the EO chain with PO, the molecule becomes a liquid.

PEL-ALC CA-205P (PPG-5-Ceteth-20)
Features/Benefits Nonionic Emulsifier (HLB 15.9) Emollient Extremely mild Adds lubricity to hair Fragrance solubilizer Hair resin plastisizer Good wetting Applications Lotions/creams Bath oils Hair sprays Shampoos/Conditioners Clear gels Antiperspirants PEL-ALC CA-205P is extremely mild as it has many moles of EO and PO. It also has a very high molecular weight, therefore making it an excellent oil in water emulsifier with a high HLB. It can be used to solubilize fragrances and to soften hair resin plastisizers like PVP. It’s highly desirable attributes make it a good fit in many different types of personal care products.

Irritation vs. other Nonionics As noted earlier, most nonionic surfactants are pretty mild, but there are exceptions. This chart shows relative skin irritation (yellow bars) and eye irritation (green bars) at 10% active ingredient at a pH 7 PEL-ALC CA-205P, circled on the left, is extremely mild – similar to PEG-20 sorbitan laurate. Others are not quite so mild – see oleth-20, C12-15 pareth-7 Even some glucosides are pretty harsh at this concentration (glucosides are generally thought of as being quite mild, but at above 5%, they do start becoming irritating

Formulation Guidelines To make O/W emulsions: To solubilize fragrance or other insoluble oils: May be added to water phase or oil phase Premix with PEL-ALC CA-205P, then add to water/surfactants phase Pretty flexible – water or oil phase HEAT water! Can be heated pretty hot (80+⁰C) without ill effects Nonionics are known to reduce the effectiveness of parabens

Other Mild Nonionics Product INCI HLB PEL-ALC CSA-25 Ceteareth-25 16.4
PEL-ALC IC-20-70 Isoceteth-20 15.5 PEL-ALC IDA-30-70 Isodeceth-30 18 PEL-ALC LA-23 Laureth-23 16.9 PEL-ALC LA-7-90 Laureth-7 12.1 PEL-ALC OD-20 Octyldodeceth-20 14 These are a few other mild alkoxylates made by Ele. You get the idea that pretty much any alcohol can be ethoxylated A few of our products… have some water to help keep them fluid. The second number, indicates the present concentration. Fore example “-90” means 90%.

PEL-SULF PEG-12D (Disodium PEG-12 Dimethicone Sulfosuccinate)
Features/Benefits Anionic Extremely mild (most mild anionic) Reduces irritation of other anionic surfactants (e.g. SLS, SLES) Low odor (lower than most competitors) Good foaming Provides light conditioning Preservative free PEL-SULF PEG-12D is the most mild anionic surfactant on the market. The 12 moles EO/PEG greatly off-sets the potential irritation of anionic surfactants. It also can reduce the overall formula irritation when using other anionics. As Elé manufactures the polyether precursor, we have better control over the process and controlling odor. Many companies have to buy the polyether. The silicone PEG also provides conditioning. Due to the inherently low water activity it is does not require any preservative.

PEL-SULF PEG-12D INCI: Disodium PEG-12 Dimethicone Sulfosuccinate
The hydrophobic tail in this case is a linear dimethicone chain rather than a fatty alkyl group. The polar head group consists of the nonionic PEG, which has been further modified with the anionic sulfosuccinate group seen here on the lower left. In this case, the molecule has a comb-like structure and actually contains three sulfosuccinate groups on average.

Irritation vs. other Anionics This chart shows relative skin irritation (yellow bars) and eye irritation (green bars) at 15% active ingredient at a pH 7 PEL-SULF PEG-12D, circled on the left, is extremely mild compared to other anionic surfactants and even other sulfosuccniates

Formulation Guidelines Add to water phase at < 55⁰C Often used as the primary surfactant in anti-acne formulations and other formulas where extreme mildness is needed such as facial cleansers and baby shampoos Blend with SLES or other anionics to reduce irritation without major decrease in foam. Reduces viscosity response Adding at <55 degrees C is recommended for all sulfosuccinates so the ester groups are not hydrolyzed For the same reason, it should not be used in formulas with very high or low pH (<4.5 or >8). In anti acne formulas it is often used at up to 30%. Like all anionics, PEL-SULF PEG-12D will reduce viscosity response with salts, but can be offset with the addition of alkanolamides In some formulas the viscosity response may be slightly depressed compared to other sulfosuccinates.

Other Mild Anionics Product INCI Description/Benefits PEL-SULF L
Disodium Lauryl Sulfosuccinate PEG-free, soft paste, useful in skin cleansers PEL-SULF LE Disodium Laureth Sulfosuccinate High foaming, available with a variety of preservative systems PEL-SULF CP Disodium Cocamido MIPA Sulfosuccinate High foaming, PEG-free, provides thickening with salt PEL-PHOS SG PPG-5 Ceteth-10 Phosphate Provides conditioning, emulsification, thickening These are all sulfosuccinate except the last one. Again, sulfosuccinates are one of the mildest types of anionic surfactant. While phosphate esters are not normally considered mild, the addition of PO to the PEL-PHOS SG greatly reduces the irritation profile.

PEL-QUAT SL-5 INCI Name: Dihydroxypropyl PEG-5 Linoleammonium Chloride
Structure: The cationic ammonium (N+) ion is shielded by the surrounding oxygen containing PEG and hydroxyl groups, thereby reducing the irritation profile.

PEL-QUAT SL-5 (Dihydroxypropyl PEG-5 Linoleammonium Chloride)
Features/Benefits Cationic Lubricious conditioning agent Substantive to hair & skin Provides very good wet comb properties to both shampoos and conditioners Compatible with anionics Applications Bath & shower products Conditioners Shampoos Styling products Antibacterial hand soaps Skin and hair are negatively charged, so the cationic charge of PEL-QUAT SL-5 makes it substantive to skin and hair. It is particularly useful for detangling formulas or for treating damaged hair. While mainly used in hair care products, it is also used in many antibacterial hand soaps.

Irritation vs. other Cationics This chart shows relative skin irritation (yellow bars) and eye irritation (green bars) at 3% active ingredient at a pH 7 PEL-QUAT SL-5, circled on the left, is extremely mild compared to other cationic surfactants The product to the right is another Elé cationic surfactant, PEL-SIL ISML.

Formulation Guidelines Add to water phase Use level 1 – 3% Especially useful in conditioners for damaged hair and detangling formulas Use at relatively low levels (1-3%). Add to water phase. Stable at typical formula manufacturing temperatures (up to 80 C) and pH ranges (3.5 – 9.5) The only Elé cationic surfactant Nexeo represents. (No Q-80)

PEL-AMPH ALP INCI Name: Arginine Lauraminopropionate Structure:
NEW patent pending amphoteric. Contains 10% Arginine Arginine is counter ion to amphoteric molecule ‘lauraminopropionate’ Arginine is 10% and acts as the counter ion to lauraminopropionate

PEL-AMPH ALP (Arginine Lauraminopropionate)
Properties 25°C Clear Gardner Color 3 Max Odor Characteristic Solids %, 29.0 – 31.0 pH, as is 9.0 – 10.0 Specific 25°C 1.03 Sold as 30% solution pH is left high which makes it self preserving (when used in a formula the pH will be lower) No preservative required

Features/Benefits Amphoteric Chloride free Compatible with wide variety of personal care ingredients Free of Prop-65 listed chemicals Excellent regulatory profile Conditioning Arginine benefits: Excellent wetting Moisture retention Good foam generation Improved barrier capacity of outermost skin layer Very mild Promotes healing Readily biodegradable Plant derived (86% Renewable Carbon Content) EO/PO free By combining the low irritation potential of an amphoteric surfactant with the soothing and conditioning properties of arginine, an exceptionally mild surfactant is created. Its benefits include ….(see slide) Free of claims…(see slide) The product is about 10% arginine, which provides moisture retention, improves the barrier capacity of skin and is said to promote healing. (we don’t make that a claim)

Features/Benefits PEL-AMPH ALP Amphoteric Yes Highly compatible with other ingredients Excellent wetting Good foam generation Very Mild Biodegradable Plant derived (86% Renewable Carbon Content) Excellent regulatory profile Free of: EO/PO, chloride, sulfates, all Prop 65 chemicals Arginine Benefits: moisture retention , improved barrier capacity, reported healing claims

Irritation vs. other Amphoterics Compared to other amphoteric surfactants at 10% active solutions and pH 7, PEL-AMPH ALP is seen to be very mild both skin and eyes – comparable to imidazoline derived amphopropionates (such as 2CSF-CG on far left) and 2C (middle). Betaines, in comparison, are primary eye irritants at this concentration.

Blender Foam Test Foam Volume Surfactant solutions were prepared at 10 ml in deionized water at 25°C. 100 mL of each solution was placed in an Osterizer and agitated at high speed for 10 seconds. Initial foam volumes and the level of the foam-water interfaces at 5 minutes were recorded. The initial foam height produced by ALP was comparable to or better than other “natural” surfactants and nearly as good as cocamidopropyl betaine. Drainage Drainage is a measure of foam stability and density. The number is the location of the foam/liquid interface after 5 minutes. The lower the number the better. Here, ALP performed equivalently or better than other tested surfactants.

Draves Wetting Draves Wetting Test Measures how quickly a surfactant solution ‘wets’ a cotton skein, causing it to sink. Wetting effects how well a surfactant will displace oil from surfaces, how well of a dispersant it will be, and the spreading of formulations. PEL-AMPH ALP, on the far right is seen to be a superior wetting agent.

Excellent Regulatory Profile
Listed on most national inventories

Formulation Guidelines General Use as secondary surfactant in mild formulations Add to water phase Thickening Like other propionates, does not thicken in response to salt addition Use polymeric thickening agent(s) such as xanthan gum etc. Alternatively, combine with sulfate/sulfonate, and amide to thicken by salt addition PEL-AMPH ALP can be used much the same as other amphoteric surfactants to formulate mild foaming products. It leaves a smooth, soft feel to skin and hair. Add to water phase with other surfactants. Like other propionates, it does not thicken in response to salt addition. It may be thickened using polymeric thickening systems such as cationic guar, xanthan gum, carbomer, etc. Alternatively, it may be thickened in combination with an anionic surfactant, such as a sulfate or sulfonate, along with an alkanolamide with salt addition. In combination with an olefin sulfonate and an amphopropionate or amphoacetate, it may be thicken simply by reducing the pH (typically to 5 – 6).

Formulation Guidelines (con’t) Compatible with: Stability Anionic surfactants Best at pH > 5 Cationic surfactants Protect from freezing Nonionic surfactants Store < 30°C Amphoteric surfactants Polymeric thickeners/conditioners Incompatible with: Oxidizing agents PEL-AMPH ALP is compatible with most other personal care ingredients. Avoid using it in the presence of oxidizing agents such as peroxides. Repeated, or prolonged freezing may cause a precipitate to form. It may be heated (up to 80 C) for limited periods. Prolonged heating will result in darkening.

PEL-AMPH ALP Foaming Facial Cleanser
Ingredient wt% Function Water 63.2 Carrier PEL-AMPH HPC-32 (Sodium Cocoamphodiacetate) 17 Surfactant Cocamidopropyl Betaine 6 Secondary Surfactant PEL-AMPH ALP (Arginine Lauraminopropionate) 12 PEL-SIL Q-80 (Quaternium-80 & Propylene Glycol) 0.5 Conditioner Phenoxyethanol Preservative Citric Acid .80 pH Adjuster Procedure: Add Water into a vessel with moderate speed mixing while heating to 500C. While heating, add the ingredients one by one with moderate mixing until each addition is homogeneous. Mix for a minimum of 30 minutes. Begin cooling to 450C and add preservative & citric acid. Mix for an additional 10 minutes. Results: Appearance: Clear pH: 6.56 Viscosity: Less than 500 cps Mild conditioning sulfate-free foaming facial cleanser. Abundant, very stable foam with moisturizing properties which leaves a smooth after- feel PEL-AMPH ALP Formulation Guide PEL-AMPH ALP can be used much the same as other amphoteric surfactants to formulate mild foaming products. It leaves a smooth, soft feel to skin and hair. Add to water phase with other surfactants. Like other propionates, it does not thicken in response to salt addition. It may be thickened using polymeric thickening systems such as cationic guar, xanthan gum, carbomer, etc. Alternatively, it may be thickened in combination with an anionic surfactant, such as a sulfate or sulfonate, along with an alkanolamide with salt addition. In combination with an olefin sulfonate an amphopropionate or amphoacetate, it may be thicken simply by reducing the pH (typically to 5 – 6).

PEL-AMPH ALP Clear Conditioning Shampoo
Ingredient wt% Function Water 66.25 Carrier Cocamidopropyl Betaine 9 Secondary Surfactant PEL-AMPH ALP (Arginine Lauraminopropionate) 11 Surfactant Sodium C14-16 Olefin Sulfonate (40%) 4 PEL-AMID CAEE (Coconut Oil Aminoethoxyethanol Amides) 3 Thickener/ Foam Stabilizer Sodium Lauroyl Methyl Isethionate 6 Preservative q.s. Citric Acid 0.25 pH Adjuster Procedure: Add Water into a vessel with moderate speed mixing while heating to 500C. While heating, add the ingredients of one by one with moderate mixing until each addition is homogeneous. Mix for a minimum of 30 minutes. Begin cooling to 450C and add phase C ingredients. Mix for an additional 10 minutes. Results: Appearance: Clear pH: 6.1 Viscosity: 5,400 cps Another sulfate-free formula, this time a conditioning shampoo. In this case, the conditioning is provided solely by PEL-AMPH ALP.

Other Mild Amphoterics
Product INCI Description/Benefits PEL-AMPH 2C Disodium Cocoamphodiacetate Very mild, non-defatting, often used as surfactants in pre-moistened wipes, baby shampoos PEL-AMPH 2CSF-CG Disodium Cocoamphodipropionate Extremely mild. Often used in neutralizing shampoos. Salt-free and methanol-free. PEL-AMPH HPC-32 Sodium Cocoamphodiacetate Mild, low-irritating, good foaming, non-defatting for baby shampoos and skin cleaners, etc. PEL-AMPH HPL-28 Sodium Lauroamphoacetate Provides a dense lather and cleans without defatting the skin All are imidazoline derived. All are mild, PEL-AMPH is the mildest PEL-AMPH HPL-28 is the lightest in color All in stock and 1 drum MOQ

Summary Surfactants vary widely in their irritation potential
Irritation Profile: Nonionic < Amphoteric < Anionic / Cationic However: there are mild choices in each category Amphopropionates<Amphoacetates<Betaines/Hydroxysultaines Sulfosuccinates<Carboxylates<Isethionates<Taurates<Sulfates Tertiary Amine salts<Quaternaries<Benzyl Chloride Quats More EO/PO = milder (all classes of surfactants) Careful surfactant choice allows mild formulations without compromising performance

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Formulating for Performance While Minimizing Irritation

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