Determining the Effect of Using Glycolic Acid in Hair Care Products Author: Jennifer M. Stasko, Associate Investigator, DuPont

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WHITE PAPER Determining the Effect of Using Glycolic Acid in Hair Care Products Author: Jennifer M. Stasko, Associate Investigator, DuPont Overview Glycolic acid is among the most popular actives in anti-aging formulations and has strong consumer recognition as an ingredient in many anti-aging skin care products. Extensive clinical data show that glycolic acid penetrates the skin effectively and stimulates cellular activity, supporting its use in a wide range of skin care products, including: cell turnover/exfoliation products; moisturizing skin lotions and creams; wrinkle reduction creams; and anti-aging creams. Although the positive effects of using glycolic acid in skin care products are well documented, similar research did not exist for the effects of using glycolic acid in hair care products. That s why DuPont, the manufacturer of Glypure, an ultra pure form of glycolic acid used in many cosmetics and personal care products, investigated the role glycolic acid could play in the formulation of hair care products. This paper provides background information about glycolic acid and a brief explanation of the complex structure of hair before discussing the experiments that were conducted by DuPont researchers and by researchers at the Textile Research Institute (TRI) in Princeton, N.J. Data from each of the four classes of experiments are presented. Based on the results from the experiments described in this paper, it is clear that glycolic acid serves several functions in hair care products. Specifically, glycolic acid can aid in conditioning hair and moisturizing both hair and scalp. As shown by the data, glycolic acid strengthens hair, prevents hair breakage and increases moisture retention in hair, giving hair overall better manageability. It is also important to note that because glycolic acid has such a positive effect on skin, hair care products with glycolic acid in the formulation will not only benefit the hair, but also moisturize the scalp and reduce flaking, resulting in an overall healthy look and feel. To assist readers who wish to further explore this topic, a list of supplemental references is provided. Glycolic Acid Glycolic acid is a carboxylic acid with alcohol functionality. It is the simplest alpha hydroxy acid (AHA) and smallest of the fruit acids. Highly soluble in water, it has low odor, low corrosiveness, very low vapor pressure and low toxicity. In addition, glycolic acid is an efficient ph adjuster, biodegradable (~90% in seven days) and non-volatile. Well known for its use in skin care products, glycolic acid has been shown to normalize the process of keratinization and therefore improve the look of the skin. Specifically, it can readjust moisture in the epidermis allowing for smoother, softer, more radiant skin. Figure 1. Chemical structure of glycolic acid H OH HO C C O H 1

Glycolic acid improves the appearance of sun damaged skin and fights skin aging by improving elasticity and firmness; increasing the production of dermal matrix compounds such as glycosaminoglycans (GAGs); and helping to increase collagen synthesis. It can also help to reduce the appearance of fine lines and wrinkles; improve skin texture; reveal smoother, brighter skin with less pigmentation; and promote the cycle of cell shedding and re-growth. Figure 2. Anatomy of hair Hair A Complex Structure Hair is a complex structure that can be broken down into four parts: the follicle, hair bulb, hair root and hair shaft. The hair shaft consists of the cuticle, cortex and medulla. The cuticle is the keratin-containing outermost protective layer composed of scale-like structures. The cortex, the largest area of the hair shaft, is the inner layer where amino acids in the form of proteins and keratin can be found. The medulla is the innermost layer which contains additional amino acids as proteins. Hair Shaft cuticle cortex medulla Hair Root Hair Bulb Follicle The Cuticle The protective layer of the hair shaft, the cuticle is made up of three distinct layers, each with a different level of the amino acid cystine in the hair protein. The outer layer of the cuticle, which is known as the epicuticle, has high cystine content; the middle layer, which is known as the exocuticle, contains a lesser amount; and the innermost layer, which is known as the endocuticle, contains a low amount. Figure 3. Scanning Electron Micrograph (SEM) of a healthy hair shaft at 1,500X magnification The smooth, scale-like structures are the cuticle, the outermost protective layer. Under the microscope, a healthy hair shaft appears to be covered in smooth, unbroken scales, as shown in figure 3. The cuticle layer is responsible for visual attributes of hair such as shine and smoothness. It is also responsible for the friction effect of hair, which determines manageability (i.e., how easy it is to comb or brush hair). The cuticle layer can be damaged by daily grooming, such as combing and brushing, as well as by chemical treatments, such as bleaching. The Cortex The cortex makes up the largest portion of the hair shaft. It contains three types of cells: orthocortical, paracortical and mesacortical, as well as macrofibrils which consist of a matrix and microfibrils. Amino acids in the form of proteins and keratin are found in this inner layer of the hair shaft. The highest concentration of disulfide bonds are in the cortex. This area of the hair shaft contains pigment and is responsible for structural integrity, strength, swelling and stretching of the hair. Experiments Four classes of experiments were conducted to evaluate the performance of glycolic acid in hair care applications. Because consumer research shows that manageability, strengthening, protection and conditioning are key attributes for hair care products, the experiments focused on these factors. Two of the classes of experiments differential scanning calorimetry (DSC) and tensile strength testing were conducted by researchers at DuPont. The other experiments repeated brushing and two separate wet combing studies were conducted by researchers at TRI Princeton. 2

All testing was performed on Caucasian hair. Both healthy and chemically damaged (bleached) hair samples were used. Plans are underway to conduct similar experiments on non-caucasian hair samples. DuPont researchers tested sets of hair samples (healthy and bleached), each treated with one of the main ingredients found in a hair conditioning treatment that is based on DuPont Glypure (see appendix for details). The ingredients in this complex formulation were tested separately to determine which, if any, would have a positive effect on hair. Stearyl alcohol and water were used as a control. In the repeated brushing experiment and one of the wet combing experiments, TRI researchers compared the effects of a hair conditioning treatment based on a DuPont Glypure starting point formulation to both a bargain brand and a high-quality brand on bleached hair samples. In another wet combing experiment, TRI researchers compared the effects of two versions of the same hair conditioning treatment based on a DuPont Glypure starting point formulation one with DuPont Glypure included and one without on bleached hair samples. For the version that did not include DuPont Glypure, citric acid was added to obtain a ph level of 4.0. Differential Scanning Calorimetry (DSC) Experiment Researchers at DuPont used DSC to study the denaturation of keratin in hair. During this experiment, high-pressure DSC was performed to determine the temperatures at which water separates from keratin and the temperature at which keratin denatures. The test method used was based on that referenced in Characterizing Keratins Using High-Pressure Differential Scanning Calorimetry (HPDSC) by Wortmann and Deutz. 1 A total of 10 hair tresses five healthy and five bleached samples were used in this experiment. One healthy hair sample and one bleached sample were treated with stearyl alcohol and water as a control. One healthy hair sample and one bleached sample were treated with a 5% DuPont Glypure solution. One each of the remaining three healthy hair samples and three bleached samples were treated with either Dow Corning 2-8194 Microemulsion, Bioplex Cetylsil S or Incroquat Behenyl TMS in the percentages found in the hair conditioning treatment that is based on DuPont Glypure (see appendix for details). All samples were treated for 5 minutes. As shown in figure 4, there was a 6.5 C increase in temperature for the healthy hair sample treated with DuPont Glypure and a 2.5 C increase in temperature for the bleached hair sample treated with DuPont Glypure. Hair samples treated with the other three ingredients showed either virtually no change or a slight decrease in temperature. This finding reveals a significant increase in the temperature at which tightly bound water separates from keratin, reflecting the moisturizing effect of glycolic acid on hair. Simply stated, this proves that hair both healthy and bleached is able to hold moisture at higher temperatures or longer times when treated with DuPont Glypure, an important benefit for hair that is styled with high-wattage blow driers, hot curlers, curling irons and straightening irons, or subjected to other conditions that are stressful to hair. 3

Figure 4. Results from DSC experiment using high-pressure method 1 Stearyl alcohol & water (control) 152.07 Healthy Hair Glycolic Acid Dow Corning 2-8194 Microemulsion Bioplex CetyIsil S 151.87 152.38 158.51 Incroquat Behenyl TMS 152.24 Stearyl alcohol & water (control) 154.04 Bleached Hair Glycolic Acid Dow Corning 2-8194 Microemulsion Bioplex CetyIsil S 153.36 153.66 156.68 Incroquat Behenyl TMS 152.97 I I I I I I I I I I I 150 151 152 153 154 155 156 157 158 159 160 Average recorded temperature C Tensile Strength Experiment Researchers at DuPont conducted a tensile strength experiment on both healthy and bleached tresses based on parameters discussed in Chemical and Physical Behavior of Human Hair by Clarence R. Robbins. 2 A total of 10 hair tresses five healthy and five bleached samples were used in this experiment. One healthy hair sample and one bleached sample were treated with stearyl alcohol and water as a control. One healthy hair sample and one bleached sample were treated with a 5% DuPont Glypure solution. One each of the remaining three healthy hair samples and three bleached samples were treated with either Dow Corning 2-8194 Microemulsion, Bioplex Cetylsil S or Incroquat Behenyl TMS in the percentages found in the hair conditioning treatment that is based on DuPont Glypure (see appendix for details). All samples were treated for 5 minutes. The hair tresses were tested with an Instron Tensile Testing Instrument at 6-inch lengths using a pull rate of 0.25 cm/min. The testing environment was controlled at 70 F with 65% relative humidity. As shown in figure 5, both the healthy hair and bleached hair samples show benefits from being treated with each of the four ingredients tested, including the DuPont Glypure solution. These results show an increase in both tenacity at break and toughness, proving that hair both healthy and bleached is stronger and more resistant to breakage after treatment with a hair conditioning treatment that is based on DuPont Glypure. 4

Figure 5. Results from tensile strength experiment Healthy (a ve r a g e o f 23 sam ples) Healthy 5 min Stearyl Alcohol (control) Bleached Co ntrol ( a ve ra g e o f 2 1 sam ples ) Bleached 5 min Stearyl Alcohol (control) (m icr om eter s) 73.90 21.52 (m i cr o m ete r s) 82.50 20.94 d e nier 50.92-38.01 - de ni e r e s tim ate 63.44-37.96 - In iti al M od u l u s 34.10 13.91 40.86 12.75 te n a city a t br e a k 1.31 0.52 1.46 0.44 43.12 4.11 38.99 5.55 In itia l M od u l us 23.70 15.84 42.24 13.32 te n ac ity at b r e a k 0.82 0.27 1.40 0.51 b re a k (%) 96.47 143.19 47.05 4.66 to u g hn e s s 0.35 0.15 0.37 0.13 to u gh n e s s 0.24 0.09 0.43 0.18 Healthy (a ve r a g e o f 23 sam ples) Healthy 5 min glycolic acid treatment Bleached Co ntrol ( a ve ra g e o f 2 1 sam ples ) Bleached 5 min glycolic acid treatment Std Dev (m icr om eter s) 73.90 21.52 (m i cr o m ete r s) 82.50 20.94 d e nier 50.92-40.21 - de ni e r e s tim ate 63.44-38.45 - In iti al M od u l u s (g f /d e n) 34.10 13.91 38.49 7.71 te n a city a t br e a k 1.31 0.52 1.56 0.30 43.12 4.11 43.79 3.04 In itia l M od u l us 23.70 15.84 45.25 12.70 te n ac ity at b r e a k 0.82 0.27 1.47 0.54 b rea k (%) 96.47 143.19 47.10 6.60 toughness (gf/den) 0.35 0.15 0.40 0.09 toughness (gf/den) 0.24 0.09 0.45 0.22 Healthy (a ve r a g e o f 23 sam ples) Healthy 5 min Bioplex Cetylsil S Bleached Co ntrol ( a ve ra g e o f 2 1 sam ples ) Bleached 5 min Bioplex Cetyl sil S (m icr om eter s) 73.90 21.52 (m i cr o m ete r s) 82.50 20.94 d e nier 50.92-38.80 - de ni e r e s tim ate 63.44-40.24 - In iti al M od u l u s 34.10 13.91 43.10 15.00 te n a city a t br e a k 1.31 0.52 1.54 0.50 43.12 4.11 40.22 4.21 In itia l M od u l us 23.70 15.84 43.23 17.58 te n ac ity at b r e a k 0.82 0.27 1.52 0.53 b re a k (%) 96.47 143.19 50.64 6.27 toughness (gf/den) 0.35 0.15 0.39 0.14 toughness (gf/den) 0.24 0.09 0.48 0.19 Healthy (a ve r a g e o f 23 sam ples) Healthy 5 min Dow Corning 2-8194 Microemulsion Bleached Co ntrol ( a ve ra g e o f 2 1 sam ples ) Bleached 5 min Dow Corning 2-8194 Microemulsion (m icr om eter s) 73.90 21.52 (m i cr o m ete r s) 82.50 20.94 d e nier 50.92-34.94 - de ni e r e s tim ate 63.44-43.06 - In iti al M od u l u s 34.10 13.91 45.32 19.08 te n a city a t br e a k 1.31 0.52 1.74 0.71 43.12 4.11 45.68 3.51 In itia l M od u l us 23.70 15.84 39.48 12.54 te n ac ity at b r e a k 0.82 0.27 1.34 0.45 b re a k (%) 96.47 143.19 54.27 7.92 toughness (gf/den) 0.35 0.15 0.50 0.23 toughness (gf/den) 0.24 0.09 0.49 0.22 Healthy (a ve r ag e o f 2 3 s am ple s) Healthy 5 min Incroquat Behenyl TMS Bleached ( a ve ra g e o f 21 sam p le s ) Bleached 5 min Incroquat Behenyl TMS (m i cr o m e ters) 73.90 21.52 (m i cr o m ete rs) 82.50 20.94 denier 50.92-39.67 - denier estim ate 63.44-36.12 - In itial M od u lu s 34.10 13.91 44.73 14.56 te n a city a t br ea k 1.31 0.52 1.43 0.56 e lo ng a tion at 43.12 4.11 44.13 7.50 In itia l M od u lus 23.70 15.84 44.47 16.84 te n ac ity at b r ea k 0.82 0.27 1.63 0.58 e lo ng a tion at 96.47 143.19 41.73 2.68 to u g hn ess 0.35 0.15 0.42 0.19 to u gh n e s s 0.24 0.09 0.43 0.17 5

Repeated Brushing Experiment Researchers at TRI Princeton began this experiment by bleaching four hair tresses. One was then treated for 1 minute with a hair conditioning treatment based on a DuPont Glypure starting point formulation. One was treated with a bargain brand for 1 minute and one was treated with a high-quality brand hair conditioner for 1 minute. The remaining hair tress was left untreated so it could be used as a control. The tresses were then brushed 1,000 times using a custom-made repeating brushing device and broken fibers were counted. As shown in figure 6, the hair sample treated with the conditioning treatment based on a DuPont Glypure starting point formulation showed a significant improvement over the untreated hair sample and performed as well as, or better than, the hair sample treated with the high-quality brand. The data indicate that DuPont Glypure provides superior lubrication to the hair, resulting in less friction and entanglement during brushing, which leads to significant reduction in hair breakage and improved manageability. This superior lubrication also benefits the scalp, reducing flaking and dryness. Figure 6. Results of repeated brushing experiment conducted by TRI Princeton Box plot of broken fibers after 1,000 brushes grouped by treatment 450 400 350 300 Mean Mean+/ SE 250 Mean+/ SD 200 Outliers 150 100 50 0 Untreated Bargain brand High-quality brand Conditioning treatment based on DuPont Glypure Results Level Number Mean Std. Dev. Std. Err. Mean Untreated 8 314 93 33 Bargain brand High-quality brand 8 149 53 19 8 142 48 17 Conditioning treatment based on 8 95 33 12 DuPont Glypure 6

Wet Combing Experiments Researchers at TRI Princeton conducted two wet combing experiments in accordance with a widely used method that was first published in the Journal of the Society of Cosmetic Chemists in 1976. 3 In the first experiment, the researchers tested two versions of the same hair conditioning treatment based on a DuPont Glypure starting point formulation one with DuPont Glypure as an ingredient and one without to determine the effect of glycolic acid. For the version of the formulation that did not include DuPont Glypure, citric acid was added to obtain a ph level of 4.0. Then, in the second experiment, the researchers compared this same hair conditioning treatment with DuPont Glypure as an ingredient to a bargain brand and a high-quality brand. In the first of the two wet combing experiments, TRI researchers began by bleaching three hair tresses. One was then treated for 1 minute with a hair conditioning treatment based on a DuPont Glypure starting point formulation. One was treated for 1 minute with the same hair conditioning treatment but without DuPont Glypure in the formulation. The remaining hair tress was left untreated for use as a control. The tresses were then subjected to wet combing per the test method previously cited. The amount of frictional force required to comb through the tresses was measured. As shown in figure 7, the amount of frictional force required to comb through the treated hair samples is significantly less than that required to comb through the untreated sample, proving the positive lubricity effect of the hair conditioning treatment based on a DuPont Glypure starting point formulation. This experiment further proves that the treatment containing DuPont Glypure shows a significantly superior effect compared to the same treatment without this key ingredient. This confirms that DuPont Glypure makes hair more manageable and easier to style. Figure 7. Results of wet combing experiment conducted by TRI Princeton on two versions of the same hair conditioning treatment one with and one without DuPont Glypure in the formulation Box plot of max load (gf) grouped by treatment 80 70 60 50 Mean Mean+/ SE 40 Mean+/ SD 30 Outliers 20 10 0 Untreated Conditioner without Conditioner with DuPont Glypure * DuPont Glypure ** *Conditioning treatment based on DuPont Glypure starting point formulation but without DuPont Glypure as an ingredient. **Conditioning treatment based on DuPont Glypure starting point formulation with DuPont Glypure as an ingredient. 7

Figure 7. Results of wet combing experiment conducted by TRI Princeton on two versions of the same hair conditioning treatment one with and one without DuPont Glypure in the formulation continued Results Level Number Mean Std. Dev. Std. Err. Mean Untreated 8 63.93 4.01 1.42 Conditioner without DuPont Glypure * 8 20.31 4.03 1.43 Conditioner with DuPont Glypure ** 8 12.52 2.60 0.92 *Conditioning treatment based on DuPont Glypure starting point formulation but without DuPont Glypure as an ingredient. **Conditioning treatment based on DuPont Glypure starting point formulation with DuPont Glypure as an ingredient. In the second wet combing experiment, the researchers began by bleaching four hair tresses. One was then treated for 1 minute with a hair conditioning treatment based on a DuPont Glypure starting point formulation. One was treated with a bargain brand for 1 minute and one was treated with a high-quality brand for 1 minute. The remaining hair tress was left untreated for use as a control. The tresses were then subjected to wet combing per the test method previously cited. The amount of frictional force required to comb through the tresses was measured. As shown in figure 8, the sample treated with the hair conditioning treatment based on a DuPont Glypure starting point formulation shows a significant improvement over the untreated hair sample and performs almost as well as the hair sample treated with the high-quality brand, reducing the frictional force needed to comb the hair. Reducing the frictional force makes hair easier to comb through and more manageable, two important attributes for consumers. Figure 8. Results of wet combing experiment conducted by TRI Princeton on three hair conditioning treatments Wet combing of DuPont Glypure conditioning treatment 80 70 60 50 Mean Mean+/ SE 40 Mean+/ SD 30 Outliers 20 10 0 Untreated Bargain brand hair conditioner High-quality brand Conditioning treatment based on DuPont Glypure 8

Figure 8. Results of wet combing experiment conducted by TRI Princeton on three hair conditioning treatments continued Results Level Number Mean Std. Dev. Std. Err. Mean Untreated 8 70.39 1.84 0.65 Bargain brand High-quality brand 8 14.81 1.94 0.69 8 8.89 0.79 0.28 Conditioning treatment based on 8 10.56 1.04 0.37 DuPont Glypure Conclusion Glycolic acid is a popular anti-aging active that has been used in the personal care industry for years for skin care applications. It has strong consumer recognition as an ingredient in a wide variety of anti-aging skin lotions, creams and exfoliating products. Results from experiments recently conducted by researchers at both TRI Princeton and at DuPont show that glycolic acid can also deliver important benefits for hair care products, enhancing the protection and manageability of hair by conditioning, moisturizing, strengthening and preventing breakage in both healthy and bleached hair. Adding glycolic acid to hair care formulations enables these products to provide hair with superior lubricity, which results in less friction and entanglement during combing and brushing, making hair more manageable, easier to style and significantly less prone to breakage. Hair care products with glycolic acid also strengthen the hair and help hair hold moisture at higher temperatures or longer times, enabling the use of high-temperature hair styling appliances without concerns about damaging the hair. The data from these experiments clearly show that both healthy hair and bleached hair can benefit from the multiple, positive effects that DuPont Glypure delivers in hair care product formulations. With a long-proven reputation as an effective exfoliant and moisturizer for the skin, an important additional benefit of using glycolic acid in hair care products is that it helps the scalp by adding moisture and reducing flaking. DuPont Glypure is an ultra pure form of glycolic acid that is used in many cosmetics and other personal care products. Manufactured in an ISO 9001:2000 certified facility located in Belle, W.Va., DuPont Glypure is made in a continuous process 24/7. It is currently available in a wide variety of starting point formulations. New starting point formulations are introduced regularly to meet evolving marketplace needs. In addition to reliable quality and supply, end users of DuPont Glypure have access to a dedicated, professional staff of technical service representatives, formulating chemists and analytical chemists for help with technical questions and assistance with new product development. 9

Appendix Note: For the second wet combing experiment performed at TRI Princeton, one version of this hair conditioning treatment was formulated without the inclusion of DuPont Glypure. For that version, citric acid was added to obtain a ph level of 4.0. Hair Conditioning Treatment with DuPont Glypure Ingredient Trade Name Function Manufacturer Wt% Purified Water Purified Water 70.00 Deionized Water Deionized Water Behentrimonium detangling and conditioning Methosulfate (and) Incroquat Behenyl TMS agent Cetearyl Alcohol Croda 2.50 Behentrimonium Chloride Incroquat Behenyl TMC-85 Stearyl Alcohol Lanette 18 detangling benefits, reduce static, improve body, and improve wet/dry combability Croda 0.75 viscosity regulation Cognis Ceteareth-20 Eumulgin B2 emulsifier Cognis 0.25 Disodium EDTA Dissolvine NA2-S chelating agent, stabilizer Akzo 0.05 Cetyl Triethylmonium Dimethicone PEG-8 Succinate Bioplex Cetylsil S conditioning agent Biosil 0.50 Purified Water Purified Water 10.00 Glycolic Acid (70%) Exfoliant, moisturizer, improves wet/dry combability, increases DuPont Glypure (70%) durability DuPont 4.00 Triethanolamine Trolamine 99% ph adjuster Ruger 1.50 0.75 Amodimethicone (and)trideceth-12 (and) Cetrimonium Chloride Dow Corning 2-8194 Microemulsion increases durability, shine, wet/dry combing, conditioning, reduced drying time, reduces fly aways Dow Corning 1.50 Fragrance, Dye, Botanical Extracts, Vitamins as desired as desired 0.00 Caprylyl Glycol (and) Hexylene Glycol (and) Methylisothiazolinone Spectragard preservative Inolex 1.00 (and) Water Triethanolamine Trolamine 99% ph adjuster Ruger ph 4.0-4.2 Glycolic Acid (70%) DuPont Glypure ph adjuster DuPont ph 4.0-4.2 Purified Water Purified Water qs to 100% Stability profiles of the finished product should be determined. 10

References Cited references 1. Wortmann, F.J., et al. Characterizing Keratins Using High-Pressure Differential Scanning Calorimetry (HPDSC). Journal of Applied Polymer Science 48:137-150; 1993. 2. Robbins, Clarence R. Chemical and Physical Behavior of Human Hair (Fourth Edition), pages 2, 25-50, 82 and 388; 2002. 3. Garcia, M.L., Diaz, J. Combability Measurements on Hair. Journal of the Society of Cosmetic Chemists 27: 379-398; 1976. Supplemental References Pharmaceutical Compositions and Methods for Managing Scalp Conditions (Murad, WO 00/06144). Kempers M.D., Steven et al. An Evaluation of the Effect of an Alpha Hydroxy Acid-Blend Skin Cream in the Cosmetic Improvement of Symptoms of Moderate to Severe Xerosis, Epidermolytic Hyperkeratosis, and Ichthyosis. Therapeutics for the Clinician 61:347-350; 1998. Van Scott M.D., J. and Ruey J. Yu, PhD., O.M.D. Alpha Hydroxy Acids: Science and Therapeutic Use. A supplement to Cosmetic Dermatology, October 1994. Composition for Treatment and Care of Hair and Scalp (Onitsuka et al. US Patent 6,086,861) (KAO). Methods for Managing Scalp Conditions (Murad. US Patent 6,515,007). North America: 1.888.243.4608 International: 1.302.892.7536 www.glypurecosmetics.dupont.com Copyright 2009 DuPont. The DuPont Oval Logo, DuPont, The miracles of science and Glypure are registered trademarks or trademarks of E.I. du Pont de Nemours and Company or its affiliates. All rights reserved. 9/09