Emollient Esters with Anti-microbial Properties Multifunctional Molecules

Transcription

1 Emollient Esters with Anti-microbial Properties Multifunctional Molecules Mild, Emollient, Microbiocidal

2 ABITEC Corporation History of USA Organization Stokley Van Camp Capital City Products Karlshamns USA Inc. ABITEC Corporation

3 Associated British Foods ABITEC Group AB Technologies ABITEC Corporation Cereform AB Enzymes ACH Foods SPI Polyols Cereal Industries Group George Weston Foods Group British Sugar Group Allied Foods Group Allied Bakeries Twining Crosfield Burtons Biscuits - Ryvita Retail Stores - Ireland & N. Ireland

4 ABF Financial Highlights Turnover $ 6,5 million Profit before tax $ 57 million Employees Approx 34,

5 Associated British Foods Operating in Europe, Australia, Asia New Zealand, USA and Eastern Europe World Class Starch and Sweetener Technology World Class Millers and Bakers Major Investor in Oleochemicals and Specialty Ingredients Technology

6 ABITEC GROUP CORPORATE STRUCTURE ABITEC LTD ENZYMES AB ENZYMES (Germany, Finland, USA) LIPID TECHNOLOGIES ABITEC Corporation (USA) AB Technology (UK) BAKERY IREDIENTS Cereform UK Cereform USA Mauri Products (UK) Yeast Products (EIRE)

7 ABITEC Group Business Sectors Lipid Technologies Personal Care Specialty Ingredients (Skin Care) Pharmaceutical Excipients Food emulsifiers Specialty Blending Enzymes Bakery Fruit Juice and Viniculture Industrial applications Bakery Ingredients Dough conditioners, Cake premixes and concentrates Confectionery blends and Yeast

8 ABITEC Group Lipid Technologies Company Location Product Offering AB Technology UK Food emulsifiers, chemical specialties ABITEC Corporation US Chemical specialties

9 ABITEC Lipid Technologies Production Chemistries / Processes Transesterification (Kosher) Esterification (Kosher) Distillation/Fractionation Vegetable Oil Refining & Processing Pastillation Amidation Alkoxylation (PO & EO) Quaternization (DMS)/Condensation Custom Liquid Blends Custom Organic Synthesis Flaking & Spray Chilling

10 Objective To supply mild, multifunctional, preservative-free ingredients tailored for cosmetic & personal care formulations

11 Preservatives Tested Ester INCI Name A Propylene Glycol Capmul 97 P Heptanoate B Propylene Glycol Capmul 98 P Caprylate C Glyceryl Heptanoate Capmul 77 G D Glyceryl Caprylate Capmul 78 G

12 Protocol Synthesis of esters Screening based on MIC data

13 Minimal Inhibitory Concentration Test Agar and antimicrobials blended together Poured and solidified in petri dishes Microbes grown in broth Dilution from broth made to reach the final inoculums concentration Petri dishes inoculated

14 Microorganisms Tested Escherichia coli Gram - Staphylococcus aureus Gram + Aspergillus niger Mold Candida albicans Yeast

15 Minimum Inhibitory Concentrations Concentration (%) A B C D + growth - no growth

16 Minimum Inhibitory Concentrations Escherichia coli A B C D growth - no growth

17 Minimum Inhibitory Concentrations Staphylococcus aureus A B C D growth - no growth

18 Minimum Inhibitory Concentrations Aspergillus niger A B + + C D growth - no growth

19 Minimum Inhibitory Concentrations Candida albicans A B C D growth - no growth

20 Preservatives Tested Ester INCI Name A Propylene Glycol Capmul 97 P Heptanoate B Propylene Glycol Capmul 98 P Caprylate C Glyceryl Heptanoate Capmul 77 G D Glyceryl Caprylate Capmul 78 G

21 Challenge Test TEA Stearate Lotion TEA Carbomer Lotion Foundation E. coli S. aureus A. Niger C. albicans

22 TEA Stearate Lotion Ingredients A. Deionized water, peg-7 glyceryl cocoate B. Stearic acid, caprylic/capric/ lauric triglyceride, cetyl alcohol C. Stearyl alcohol, glycol distearate, steareth-2, steareth-2 D. Triethanolamine E. Citric acid

23 TEA-Carbomer Lotion Ingredients A. Deionized water, carbomer B. Peg-7 glyceryl cocoate, stearic acid, caprylic/capric/lauric triglyceride, cetyl alcohol, glycol distearate, peg-8, ceteareth-2 C. Glyceryl tricaprylate D. TEA

24 Foundation Ingredients A. Deionized water, tea, dimethicone copolyol B. Propylene glycol, magnesium aluminum silicate C. Propylene glycol, sodium carboxymethylcellulose D. Peg-6 caprylic/capric triglycerides E. Stearic acid, propylene glycol dicaprylate/dicaprate F. Tricaprin, sorbitan laurate, cetyl alcohol

25 Challenge Test Format Grow bacteria in nutrient rich broth. Isolate bacteria, wash and re-suspend. Inoculate the lotions and foundation. Incubate inoculated bases for 28 days. Plate growth at 7, 14, 21, and 28 days.

26 Controls No preservatives Triclosan.2% (by wt.) DMDM Hydantoin.4% (by wt.) Methylparaben.2% (by wt.) Propylparaben.1% (by wt.)

27 TEA Stearate Lotion, controls Day 7 Day 14 Day 21 Day 28 % of each E. coli Triclosan.2 DMDM.4 MP.2 PP.1 S. aureus Triclosan.2 DMDM.4 MP.2 PP.1 A. niger Triclosan.2 DMDM.4 MP.2 PP.1 C. albicans Triclosan.2 DMDM.4 MP.2 PP.1 6,5 TOTAL 3,25 6,7 1 1,5 1,25 1,5 TOTAL 1,35 5,85 1,15 TOTAL 1 2,5 1,25 1,35

28 TEA Stearate Lotion Day 7 Day 14 Day 21 Day 28.5% E. coli A B C D S. aureus A B C D A. niger A B C D C. albicans A B C D 1,25 6 1, TOTAL 1, TOTAL 55 1,9 5,7 6,75 55 PARTIAL 3, ,5 8,5 7,5

29 TEA Carbomer Lotion, controls Day 7 Day 14 Day 21 Day 28 % of each E. coli Triclosan.2 DMDM.4 MP.2 PP.1 S. aureus Triclosan.2 DMDM.4 MP.2 PP.1 A. niger Triclosan.2 DMDM.4 MP.2 PP.1 C. albicans Triclosan.2 DMDM.4 MP.2 PP.1 5 TOTAL 19,5 4,75 TOTAL 3,6 1,1 1,15 PARTIAL 1 2,1 5 PARTIAL 7,8

30 TEA Carbomer Lotion Day 7 Day 14 Day 21 Day 28.5% E. coli A B C D S. aureus A B C D A. niger A B C D C. albicans A B C D 4,7 7 1,2 75 2,5 TOTAL TOTAL TOTAL TOTAL 8 5,5 95 TOTAL TOTAL 3 55 PARTIAL PARTIAL PARTIAL TOTAL 8 PARTIAL TOTAL PARTIAL TOTAL

31 Foundation, controls Day 7 Day 14 Day 21 Day 28 % of each E. coli Triclosan.2 DMDM.4 MP.2 PP.1 S. aureus Triclosan.2 DMDM.4 MP.2 PP.1 A. niger Triclosan.2 DMDM.4 MP.2 PP.1 C. albicans Triclosan.2 DMDM.4 MP.2 PP.1 2 3,6 PARTIAL 25,5 8,95 15, TOTAL 13,1 1,1 1,4 1, ,85 TOTAL PARTIAL 22, TOTAL 5

32 .5% Day 7 Day 14 Day 21 Day 28 E. coli A B C D S. aureus A B C D 3, A. niger A B C D TOTAL PARTIAL TOTAL C. albicans A B C D 2,55 13,5 2 1,15 Foundation

33 Synergies Esters exhibit certain amount of organism specificity

34 TEA Stearate Lotion, controls Day 7 Day 14 Day 21 Day 28 % of each E. coli Triclosan.2 DMDM.4 MP.2 PP.1 S. aureus Triclosan.2 DMDM.4 MP.2 PP.1 A. niger Triclosan.2 DMDM.4 MP.2 PP.1 C. albicans Triclosan.2 DMDM.4 MP.2 PP.1 6,5 TOTAL 3,25 6,7 1 1,5 1,25 1,5 TOTAL 1,35 5,85 1,15 TOTAL 1 2,5 1,25 1,35

35 TEA Stearate Lotion and Blends Day 7 Day 14 Day 21 Day 28 % of each E. coli A,B.25 A,D.25 S. aureus A,B.25 A,D.25 A. niger 1,35 8 2,75 5 A,B.25 A,D.25 C. albicans PARTIAL A,B.25 A,D.25 1,7 1,15

36 TEA Stearate Lotion and Blends Day 7 Day 14 Day 21 Day 28 % of each E. coli A,B.125 A,B.25 A,D.125 A,D.25 S. aureus A,B.125 A,B.25 A,D.125 A,D.25 A. niger A,B.125 A,B.25 A,D.125 A,D.25 C. albicans A,B.125 A,B.25 A,D.125 A,D.25 TOTAL PARTIAL PARTIAL ,2 25 1,35 8 PARTIAL 1,85 1,7 3,3 1,3 9, 1,25 2,75 TOTAL 55 1,15 19, ,7 1,15 6,

37 Additional Work A repeat of the MIC test, using a slightly different scoring method was performed at an outside laboratory, Lyle Labs in Ohio. Of particular interest were the fungi, yeast and pseudomonas findings of our clients. Finally, we tested for possible synergies with the parabens family of preservatives.

38 MIC Test, Lyle Laboratories 77G 2% 1%.5% 98P 2% 1%.5% A. niger A. niger C. albicans 2 C. albicans E. coli E. coli K. pneu. K. pneu. P. aerug. 3 4 P. aerug S. choler. S. choler. 1 S. aureus 4 S. aureus 2 2 S. epider. 1 4 S. epider P. acnes 1 4 P. acnes 4 4 4

39 MIC Test, Lyle Laboratories 78G Trial 1 2% 1%.5% 78G Trial 2 2% 1%.5% A. niger A. niger C. albicans C. albicans 2 E. coli E. coli K. pneu. K. pneu. P. aerug P. aerug S. choler. S. choler. S. aureus 1 S. aureus 1 S. epider. 1 S. epider. 1 2 P. acnes 1 P. acnes 1 2

40 MIC Test, Lyle Laboratories 97P Trial 1 2% 1%.5% 97P Trial 2 2% 1%.5% A. niger A. niger 1 1 C. albicans C. albicans E. coli E. coli K. pneu. K. pneu. P. aerug P. aerug S. choler. S. choler. S. aureus S. aureus 1 2 S. epider. S. epider. 1 2 P. acnes P. acnes 1 2 2

41 MIC Test, Lyle Laboratories 3parts methyl/1part propyl (.12g/.4g) 2% 77G in 3:1 methyl/propyl paraben A. niger A. niger C. albicans C. albicans E. coli E. coli K. pneu. K. pneu. P. aerug. 2 P. aerug. S. choler. S. choler. S. aureus S. aureus S. epider. 1 S. epider. P. acnes 1 P. acnes

42 Antimicrobial Properties Organism specificity Formulation specificity Ester blend synergies Other preservative synergies.

43 Product Characteristics Stable to heat Stable to high sheer Oil phase soluble W/O primary emulsifiers Secondary emulsifiers No post addition necessary

44 HLB Values (calculated) Propylene Glycol Heptanoate (A) 5. Propylene Glycol Caprylate (B) 4.4 Glyceryl Heptanoate (C) 7.2 Glyceryl Caprylate (D) 6.6

45 Product Characteristics Non-greasy emollient Rubs quickly into the skin Light conditioning after feel Water white color Slight characteristic odor

46 Red Blood Cell Test In-Vitro Irritation Test Blood cell hemolysis Hemoglobin denaturation Results Expressed As L/D Scores L = Cell lysis D = Protein denaturation

47 Score Range.1-1 Irritant 1-1 Moderate Irritant 1-1 Slight Irritant >1 Non-Irritant

48 Modifications All Preservatives tested in 5:5 water:ethanol blend Concentration of Preservative A raised.1% to 1.%

49 Red Blood Cell Test Results PRESERVATIVE L/D A B 14.2 C 16.5 D 1.6

50 Patents and References Okumura, M. Effect of monoglycerides on the percutaneous absorption of papverine hydrochloride Drug Des. Delivery, 6(2),

51 Patents and References Birkhahn, R., McMenany, R., and Border, J. Intravenous feeding of the rat with short chain fatty acid esters I. Glycerol monobutyrate Am. J. Clin. Nutr. 3(12),

52 Patents and References U.S. Patent 4,2,775 issued to Kabara teaches a food grade microbicidal composition having a monoester with C 12 aliphatic fatty acid as its primary microbicide

53 Patents and References Kabara, Jr., Ohkawa, M., et al. Examination on Antitumor, Immunological and Plant-Growth Inhibitory Effects on Monoglycerides of Caprylic, Capric and Lauric Acids and Related Compounds, Pharmacological Effects of Lipids, Volume II, Pgs (1985).

54 Patents and References Branan, A. and Davison, P. Antimicrobials in Foods,, Marcel Dekker, New York 1983, Pgs teaches the use of saturated, unsaturated and esters of fatty acids as antimicrobials and the use of compounds for food preservation.

55 Additional Information Ester INCI Name CAS number EINECS JCI A Propylene Glycol Heptanoate Capmul 97 P No B Propylene Glycol Caprylate Capmul 98 P , No No C Glyceryl Heptanoate Capmul 77 G No No D Glyceryl Caprylate Capmul 78 G

56 Conclusions Preservative-Free Claims Non-Irritating Multifunctional - Preservative - Emollient - Delivery vehicle - Emulsifier