UV Protection by Ciba
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1 UV Protection by Ciba Ciba Specialty Chemicals Holding Inc.; All rights reserved. The information given in the documentation is based on the present state of our knowledge. It shows without liability on our part the uses to which our products can be put. 1
2 UV Absorbers overview UV-A Test Methods (in vivo / in vitro) UV Protection by Ciba TINOSORB M TINOSORB S Registration status Market Products with Ciba UV Absorber 2
3 Protection at the beach around
4 Objective: Tanning without Sunburn, 1930 First transparent sun protection creams From Tavenrath Simone,
5 Skin cancer as headline, Germany 1993 Dangerous sun: How to save our skin From Tavenrath Simone, 2000 Warnings from: Sun Allergy Photodermatosis Sunburn Skin-aging Skin cancer 5
6 UV exposure of the skin Spectrum of the Sun Stratosphere Ozone layer Surface of the earth UV-C UV-B UV-A Visible light Infrared UV-B: 70% reflected by Stratum Corneum UV-A: 30% penetrates into Dermis Horny layer of the skin Epidermis Dermis Hypodermis Wavelength nm
7 Penetration of Sun Light Wavelength [nm] Penetration Depth [µm] 1, Penetration Depth / µm UVB UVA SC Wavelength / nm 7
8 Effects of UV Radiation on Human Skin Main risk of UVB nm Sunburn Main risk of UVA nm Accelerated photoageing Skin cancer Damage of blood vessels and connective tissues Contribution to sunburn Contribution to skin cancer 8
9 Requirements of UV Absorbers Efficacy Molecules have to provide an efficient absorption of UV radiation (UVB and/or UVA) Ease of Formulating Molecules have to be compatible with most ingredients used in formulations Safety Molecules have to be safe, i.e. avoid of adverse effects 9
10 Most frequently used cosmetic UV Absorbers 10
11 UV-Filter consumption in Western Europe TiO2 ZnO ZnO EHMC Other BP4 OT PSA 14% 3% 41% EHMC TiO2 Other 20% 4% 18% 13% OCT BP3 BP4 14% EHS MBC BMBM 9% 11% OCT OT PSA BP3 MBC EHS BMBM Volume: Total 4840 t Value: Total 97.3mio Kline
12 Two most frequently used absorbers for UV-B and UV-A O O O O O UV-B: EthylHexyl MethoxyCinnamate (EHMC) OCH 3 UV-A: Butyl MethoxyDibenzoylMethane (BMBM) Molar Extiction Molar Extiction Wavelength (nm) The ideal combination? Wavelength (nm) 12
13 Photostability of BMBM and EHMC UVA/UVB-Ratio 1,00 0,80 0,60 0,40 0, % BMBM BMBM + 5% OCR + 5% OCR and 5% EHMC dashed lines: irradiation with 10 MED BMBM/EHMC combinations are not photostable 13
14 New UVA- and Broad-Spectrum UV Filters, 2003 # INCI Tradename UVB UVA Approved (Europe) Freely available S 71 S 73 S 79 S 80 S 81 TDSA DTS MBBT DPDT BEMT MEXORYL SX MEXORYL XL TINOSORB M NEOHELIOPAN AP TINOSORB S X X X X X X X X no no 14
15 UV Absorbers overview UV-A Test Methods (in vivo / in vitro) UV Protection by Ciba TINOSORB M TINOSORB S Registration status Market Products with Ciba UV Absorber 15
16 UV-A Test Methods (in-vivo / in-vitro) 16
17 In vivo: UVA-PF (PPD) Persistant Pigment Darkening = PPD Principle: Measurement of UVA-induced pigmentation 2 hours after irradiation when the pigmentation has stabilized. Conditions: UVA-dose about 15 J/cm² 10 volunteers of skin types 2,3 and 4 The Minimal Pigmenting Dose (MPD) corresponds to the minimal UVA dose producing the first perceptible pigmentation 2 hours after exposure to 6 increasing doses of UVA. Protected area is then compared with unprotected area. UVA PF = MDPp / MPD np 17
18 In vitro: Australian Standard Principle: 100 Measurement of the UVA-transmission of the formulation at d=0.0008cm between 320 and 360nm Definition: Transmission < 10% at any wavelength in this range 80 Transmission (%) Australian Standard λ (nm) 18
19 In vitro: UVA/UVB-ratio Principle: Ratio of the average of extinction E in the UVA- and the UVBrange, spectrum measured on special substrates UV-B UV-A E (1%,1cm Wavelength / nm UVA-UVB ratio of around 1 = broad band filter system UVA-UVB ratio of < 0.5 = UVB absorber UVA-UVB ratio of > 1 = UVA absorber 19
20 Star-rating UV-A / UV-B ratio = = = > 0.8 = 20
21 In vitro: Critical Wavelength Principle: l c is the upper limit of the spectrum from 290nm on, within which 90% of the area under the extinction curve of the whole range between 290 and 400nm is covered λ c E (1%,1cm Wavelength / nm The higher the l c = The better the UVA protection 21
22 Photostable UVA Protection Traditional combination of BMBM (Parsol 1789) and EHMC are effective, but not photostable. Stabilization with OCR is effective for BMBM alone, but not in combination with EHMC TINOSORB M and TINOSORB S are the only broad spectrum and photostable UV Absorbers available on the market 22
23 UV Absorbers overview UV-A Test Methods (in vivo / in vitro) UV Protection by Ciba TINOSORB M o Properties o Performances o Formulating with TINOSORB M TINOSORB S Registration status Market Products with Ciba UV Absorber 23
24 TINOSORB M Organic Micropigment with Broad-Spectrum UVA/UVB Performance and High Inherent Photostability 24
25 Chemical Properties Active Ingredient of TINOSORB M: INCI name: Methylene Bis-Benzotriazolyl Tetramethylbutylphenol (abbr.: MBBT) N OH OH N Melting point: 195 C Solubility in H 2 O: < 10-8 g/l Molecular mass: g/mol N N N N UV absorbance E1%,1cm 25
26 Physical Properties The micronization is performed with a ball milling process ending up with an aqueous dispersion of microfine MBBT particles (d 0.5 <200nm): Atomic Force Microscopic Image of TINOSORB M (Particle Size Range: 70 nm nm = 0,07µm - 0,40µm) 26
27 Composition of TINOSORB M MBBT particles 50.0% Surfactant (Decyl Glucoside) 7.5% Thickener (Xanthan gum) 0.2% Propylene glycol 0.4% Water ad 100% ph No preservation necessary because of alkaline ph 27
28 Importance of small particle sizes The smaller the particle size, the higher the molar extinction of TINOSORB M Particles Molar Extinction / l/(mol cm d(0.5) = 0.16 µm d(0.5) = 0.21 µm d(0.5) = 0.34 µm d(0.5) = 0.78 µm d(0.5) = 4.37 µm Wavelength / nm 28
29 Importance of small particle sizes Qualitative Explanation of the Increase of in vitro SPF with Smaller Particles The UV-attenuating coverage by the sunscreen film is more efficient with smaller particles. Average thickness of film: 20 µm; 10% particles =20% TINOSORB M Assumption: two layers of particles for an efficient coverage particle size d (µm) ,5 1,25 Max. coverage 10% 20% 40% 80% 29
30 ph Stability of TINOSORB M TINOSORB M dispersion in water 2, ph value Stable formulations in a broad ph range possible 30
31 Concentration / SPF correlation SPF calc % TINOSORB M 6,6% TINOSORB M are required to fulfill Australian standard TINOSORB M is recommended up to 20% in cosmetic formulations 31
32 Synergistic effect of TINOSORB M and EHMC SPF in-vivo % TINOSORB M 5% EHMC 5% EHMC + 8% TINOSORB M 5% EHMC + 20%TINOSORB M 32
33 TINOSORB M and TiO 2 3.5% TiO2 8% TINOSORB M 1,2000 1,2000 1,0000 1,0000 Extinction 0,8000 0,6000 0,4000 Extinction 0,8000 0,6000 0,4000 0,2000 0,2000 0,0000 0, Wavelength / nm Wavelength / nm Combination 1,2000 SPF calc. = 12 Crit. Wavelength = 385 UVA/UVB ratio: 0.8 Australian Standard Fulfilled Star Rating: Extinction 1,0000 0,8000 0,6000 0,4000 0,2000 0, Wavelength / nm 33
34 Comparison of UVA Performance UV-Absorber Australian Standard UVA/UVB Ratio Critical Wavelength (nm) TINOSORB M 6.6% ZnO (Nanox) 8% BMBM (Parsol 1789) 3% TiO2 9% Benzophenone-3 > 10% Ethylhexyl Triazone >20% Ethylhexyl Methoxycinnamate >10% Octocrylene >10% 0,
35 Synergistic effect of TINOSORB M with EHMC ZnO TINOSORB M ZnO & 5% EHMC TINOSORB M & 5% EHMC UVA-PF % UVA Filter (ZnO or TINOSORB M) 35
36 Photostability in vitro TINOSORB M EHMC BMBM MBC % recovery of UV-Filters UV-Dose in MED Minimal Erythemal Dose Max MED in Central Europe 36
37 Stabilization of EHMC by TINOSORB M Recovery of EHMC in% EHMC alone 2.4% EHMC & TINOSORB M 10% 0 10 UV-Dose in MED 37
38 Formulation Guideline with TINOSORB M Optimized way of incorporation After emulsification, during the cooling phase (~60 C), pour TINOSORB M into the emulsion under gentle stirring. Additional homogenization should be avoided. Alternative way of incorporation Incorporation of TINOSORB M into the water phase under continuous stirring prior to the emulsification at 75/80 C Incorporation into the oil phase has to be avoided Exposition time at high temperatures should be as short as possible 38
39 UV Absorbers overview UV-A Test Methods (in vivo / in vitro) UV Protection by Ciba TINOSORB M TINOSORB S o Properties o Performances o Formulating with TINOSORB S Registration status Market Products with Ciba UV Absorber 39
40 TINOSORB S The most efficient Broad-Spectrum UV-Absorber 40
41 Chemical Properties INCI name: Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine (abbr.: BEMT) OCH 3 Melting point: 80 C Solubility: Oil soluble Molecular mass: 627,8 g/mol Solubility in H 2 O: 10-7 g/l O HO N N N OH O 800 UV-spectrum of TINOSORB S E (1%, 1cm Wavelength / nm 41
42 Inherent Photostability by Photo-Tautomerism R 1 R 4 N N O H R 2 N R 5 R 3 h n R 1 R 4 N N O H R 2 N R 5 R 3 42
43 UV-A Protection with TINOSORB S Placebo TINOSORB S plus 5% EHMC PFA (PPD method) Placebo 1% 2% 4% % TINOSORB S PFA (Japan) PA +++ PA ++ PA + 43
44 Comparison of UVA Performance UV-Absorber Australian Standard UVA/UVB Ratio Critical Wavelength (nm) TINOSORB S 2% TINOSORB M 6.6% ZnO (Nanox) 8% BMBM (Parsol 1789) 3% TiO2 9% Benzophenone-3 > 10% Ethylhexyl Triazone >20% Ethylhexyl Methoxycinnamate >20% Octocrylene >20% 0,
45 Synergistic effect of TINOSORB S with EHMC UVA-PF BMBM BMBM & 5% EHMC & 5% OCR TINOSORB S TINOSORB S & 5% EHMC % UVA Filter (BMBM or TINOSORB S) 45
46 TINOSORB S and Ethylhexyl Triazone Extinction 1,6000 1,4000 SPF calc. 7 4% EHT 1,2000 1,0000 0,8000 0,6000 0,4000 0,2000 0,0000-0, Wavelength / nm Extinction 3% TINOSORB S 1,6000 1,4000 1,2000 1,0000 0,8000 0,6000 0,4000 0,2000 0, Wavelength / nm SPF calc. 6 Combination SPF calc. = 20 Crit. Wavelength = 371 UVA/UVB ratio: 0.48 Australian Standard Fulfilled Star Rating: Extinction 1,6000 1,4000 1,2000 SPFcalc. 20 1,0000 0,8000 0,6000 0,4000 0,2000 0, Wavelength / nm 46
47 Photostability in vitro TINOSORB S EHMC BMBM MBC % recovery of UV-Filters UV-Dose in MED Minimal Erythemal Dose Max MED in Central Europe 47
48 Stabilization of BMBM by TINOSORB S 100 Recovery of BMBM in % BMBM alone BMBM & 3%TINOSORB S 0 10 UV-Dose in MED 48
49 Formulation Guideline with TINOSORB S Solubilize TINOSORB S by adding it directly to the oil phase and heat up to 80 C. For cold process : solubilize TINOSORB S in the most polar oil Emulsification at room temperature O/W Emulsions Need of sufficient polar oils for solubilization Reasonable limit of use in O/W : < 5% W/O Emulsions Need of sufficient polar oils for solubilization Use of minimal quantity of non-polar oils for W/O s stability Reasonable limit of use in W/O : < 3% 49
50 Solubility of TINOSORB S Very good solubility (15-20%) UV Absorbers, Pyrrolidones Good solubility (8-15%) Fatty Acids Esters, Benzoic Acid Esters Low solubility (2-5%) Triacylglycerides, vegetables oils Very Low solubility (<1%) Alcohol, silicones and hydrocarbon derivates 50
51 Solubility of TINOSORB S Fatty Acid Esters Isodecyl Salicylate (Dermol IDSA) 18% Diethylhexyl Succinate (Crodamol OSU) 10% Dicaprylyl Carbonate ( Cetiol CC) 9% Propylene Glycol Dicaprylate/Dicaprate (Crodamol PC) 7% Isopropyl Myristate ( Tegosoft M) 6% Benzoic Acid Esters C12-C15 Alkyl Benzoate (Tegosoft TN) 13% Isostearyl Benzoate (Finsol SB) 8% Triacylglycerides Caprylic/Capric Triglyceride (Miglyol 812) 5% Pyrrolidones Caprylyl Pyrrolidone (Sulfadone LP100) 20% UV Absorbers Ethylhexyl Methoxycinnamate (TINOSORB OMC) 17% Ethylhexyl Salicylate (Eusolex OS) 20% 51
52 TINOSORB M & TINOSORB S the ideal couple 52
53 Characteristics of TINOSORB M & TINOSORB S TINOSORB M TINOSORB S Physical state Particles dispersion Powder Emulsion Phase Broad-spectrum Performance Critical Wavelength Water Covers long UVA 388nm Oil Higher absorbance 373nm UV-A/UV-B ratio
54 Synergy between TINOSORB M & TINOSORB S TINOSORB M conc. 0% 5% 10% 15% TINOSORB S 0% TINOSORB S 2% 54
55 Summary TINOSORB M unique micronized organic particles broad band absorption wide coverage of UVA range Excellent photostability Synergy with most UV-B absorber TINOSORB S the first cosmetic UV-filter based on innovative HPT technology superior full spectrum protection oil solubility = formulation flexibility high efficacy at low concentrations = ideal for day care Photostable Synergy with most UV-B absorber 55
56 UV Absorbers overview UV-A Test Methods (in vivo / in vitro) UV Protection by Ciba TINOSORB M TINOSORB S Registration status Market Products with Ciba UV Absorber 56
57 Registration Status 57
58 TINOSORB M & TINOSORB S Registration Approved as UV filter in: Europe in a concentration of use up to 10% active (=20% TINOSORB M) (European cosmetics directive 76/768/EEC) Switzerland Brazil Paraguay Argentina Bolivia Uruguay French Guyana South Africa China Australia (only TINOSORB M) Taiwan 58
59 TINOSORB M & TINOSORB S Registration No registration of the raw material required. Sunscreen products have to be registered by Ministry of Health. Colombia Chile Ecuador Peru Korea Ongoing registration work: USA Japan Mexico Canada Sunscreen products are free to be placed on the market as long as no therapeutic claims are made: Honkong Singapore 59
60 UV Absorbers overview UV-A Test Methods (in vivo / in vitro) UV Protection by Ciba TINOSORB M TINOSORB S Registration status Market Products with Ciba UV Absorber 60
61 French Market All Pharmacy Brands (except L Oréal Brands) use TINOSORB M All Pharmacy Brands use Ciba Technology About 20 Brands on Market incorporate TINOSORB M and/or TINOSORB S 61
62 German Market BDF is most important purchaser of TINOSORB S (e.g. Nivea) Premium Brand Marbert incorporates TINOSORB First Private Label products on market with TINOSORB M 62
63 Swiss Market Highest per capita spendings on sunscreen Three out of the top four Sun Care Brands use TINOSORB (Nivea Sun, Daylong, Ambre Solaire, Sunlook) All PizBuin products contain TINOSORB M and TINOSORB S Private Label sunscreen with TINOSORB M launched
64 Other Markets ESP No 1 Brand Nivea uses TINOSORB S Pharmacy brands ISDIN (A. Puig) and E.Carreras (Novartis) incorporate TINOSORB M GBR Two strong Mass Market brands use TINOSORB (Nivea, PizBuin) Incorporation of TINOSORB M in some Private Label products (Superdrugs s Solait, M&S, Tesco) ITA Market Leader Nivea incorporates TINOSORB S Local Brands (Collistar, Bottega Verde, Biovitamin C, Bio Nike) use TINOSORB M in some of their formulations 64
65 Ingredient Branding (official) RoC Minesol, Europe Co-Branding Daylong, Switzerland No more suntan, India 65
66 Ingredient Branding (inofficial) Bergasol, France Lutsine, France Ella Baché, France Polysianes, France Shandiz, Iran 66
67 Ciba Sunscreen Simulator 67
68 Ciba Sunscreen Simulator 68
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