Application of Analytical Techniques to Cosmetics. Dr. Joyce Zhao Senior Chemist/Study Director at Jordi Labs Jan. 19 th, 2017
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1 Application of Analytical Techniques to Cosmetics Dr. Joyce Zhao Senior Chemist/Study Director at Jordi Labs Jan. 19 th, 2017
2 Jordi Labs Jordi Labs: A leader in analytical chemistry Founded in 1980 Over 1000 projects completed annually State of the art facilities and instrumentation 80% of staff are degreed chemists (Ph.D., M.S., B.S.) Cosmetic Analysis Identification/Quantification Investigative Analyses Deformulation/Reformulation Purity analysis Quality control testing Pigment analysis Regulatory analysis
3 Overview Goals Deformulation of cosmetics Quality control testing Pigment analysis Regulatory analysis Purity analysis Techniques Qualitative and Quantitative Study through: LCMS QToF-LCMS-UV-CAD QQQ-LCMS FTIR Microscope SEM-EDX GCMS QToF-GCMS Pyrolysis-GCMS (PYMS) Headspace-GCMS GPC, IEC, ICPMS, TGA, DSC, NMR and many more
4 Deformulation Test Article #1: Bar Soap Analysis Methods: -LCMS for polar/ionizable compounds: e.g. detergents -GCMS for non-polar and volatile compounds: e.g. fragrances -SEM/EDX for elemental composition -DSC for insight into the material structure. Quadrupole Time-of-flight Liquid chromatography mass spectrometry (QToF-LCMS): - Accurate mass analysis for elemental formula determination - Database searches to correlate mass spectra to know reference compounds - MS/MS, HPLC-NMR and HPLC-FTIR analysis for structure elucidation - Verification with authentic reference material for retention time matching Sample Preparation: 1 mg/ ml in methanol
5 Deformulation Identification of compounds in positive and negative modes: RT Positive m/z Negative m/z LCMS Results of Soap Sample Mass Best Match Score Diff. Possible ID C 2 H 6 O 4 S C 10 H 20 O 5 S C 12 H 24 O 5 S C 14 H 28 O 5 S C 14 H 28 O 3 S C 16 H 32 O 5 S Hydroxyethanesulfonic acid 2- (Heptylcarbonyloxy)ethanes ulfonic acid 2- (Nonylcarbonyloxy)ethanesu lfonic acid 2-Lauroxyethanesulfonic acid 1-Tetradecene-1-sulfonic acid 2-Myristoxyethanesulfonic acid C 12 H 24 O Lauric acid C 16 H 32 O 3 S C 18 H 36 O 5 S C 20 H 40 O 5 S Hexadecene-1-sulfonic acid 2-Palmitoxyethanesulfonic acid 2-Stearoxyethanesulfonic acid C 16 H 32 O Palmitic acid C 18 H 34 O Octadecenoic acid C 18 H 36 O Stearic acid Results: Detection of detergents C 34 H 66 O Ethylene palmitate C 39 H 74 O Trilaurin C 36 H 70 O C 41 H 78 O (Palmitoyloxy)ethyl stearate 2,3- Bis(dodecanoyloxy)propyl myristate
6 Deformulation Quantitation of each compound: Detector: UV/Vis CAD (charged aerosol detector) Quantitation method: Formal quantitation compares the observed signal for each compound against a calibration curve made using the same compound. Relative quantitation utilizes internal standards of different chemistry from the target analyte to estimate the concentration of the target molecule.
7 Deformulation Quadrupole Time-of-flight Gas Chromatography Mass Spectrometry (QToF-GCMS) Sample Preparation: 1 mg/ ml in methanol RT Possible ID CAS Molecular Formula Dodecanoic acid, methyl ester C13H26O Tridecanoic acid, 12-methyl-, C15H30O2 methyl ester Hexadecanoic acid, methyl C17H34O2 ester Methyl stearate C19H38O2 Results: Detection of esters - known artificial fruit and flower fragrance 7
8 Deformulation Scanning Electron Microscopy with X- ray microanalysis (SEM-EDX) Differential scanning calorimetry (DSC) Elemental Composition of Area 1 Element Weight % Mole % Carbon Oxygen Sodium Sulfur Chlorine
9 Deformulation Summary of Soap Deformulation: Analysis Method LCMS GCMS SEM/EDX DSC Results Detection of aliphatic sulfonic acids - detergents Detection of esters - known artificial fruit and flower fragrance Detection of C, O, Na, S and Cl Sample is consistent with a mixture of compounds Other analysis: -IEC: Concentration of soluble ions: NO 3- /NO 2- ; ClO 2- /ClO 3 - -ICPMS: Concentration of elements: scans 69 elements -FTIR: Bulk Chemistry 9
10 Deformulation Test Article #2: Rose Analysis Method: Dynamic Headspace Gas Chromatography Mass Spectrometry (DHSGCMS) Summary of Red Rose Analysis Possible ID CAS Comment α-pinene pine odor β-pinene pine odor Limonene citrus Phenyl ethyl alcohol floral odor Acetic acid phenylethylester floral odor 3-hexene-1-ol-acetate sharp fruitygreen Vinyl anisole - sweet odor Caryophyllene spicy odor 1-ethenyl-4-methoxybenzene floral odor 3,5-Dimethoxytoluene floral odor 1,3,5-trimethoxybenzene floral odor Theaspirane herbal odor α,β-dihydro-β-ionone floral odor Results: 3,5-dimethoxy-toluene as the most abundant component 10
11 Brand Name vs. Generic Test Articles #3: Designer Perfume and Imitation Product Analysis Method: Thermogravimetric Analysis (TGA) Solvent Evaporation and thermal degradation of the fragrance components Results: The Designer sample was found to contain larger fragrance content, and correspondingly a lower amount of ethanol. 11
12 Brand Name vs. Generic Analysis Method: Desorption Mass Spectroscopy (DMS) and Gas Chromatography - Flame Ionization Detector (GC-FID) X indicates that a particular compound was detected in the sample. Results: The Designer sample was found to contain some additional fragrance components and a UV-B absorber. 12
13 Quality control testing Comparison of soap Lot #1004 and Lot #1007: GCMS and LCMS Results: The two lots have good reproducibility 13
14 Purity Test Article #4: A bar soap with visible crystals blooming to the surface Analysis Method: -Fourier transform infrared spectroscopy (FTIR) : identify the general class of the material 14
15 Purity Crystal from Soap Sodium gluconate: a chelating reagent Sodium Gluconate Standard FTIR Peaks and Identifications Possible IR Frequency (cm -1 ) Functional Group Possible Source 3541, 3430, 3308, 3165 O-H stretch Sodium gluconate 2969, 2925, 2866 Aliphatic C-H stretch Sodium gluconate 1609 C=O stretch Sodium gluconate 1472, 1443, 1407 C-H bend Sodium gluconate 1308, 1281 C-H rock Sodium gluconate 1093, 1064, 1035 C-O stretch Sodium gluconate 950 O-H bend Sodium gluconate 733 (COO)- rock Sodium gluconate Soap Blank Results: The crystals in the soap are consistent with sodium gluconate 15
16 Pigment Analysis Test Articles #5: A matte brown eye shadow and a glitter brown eye shadow Matte eye shadow Analysis Method: -SEM/EDX: elemental composition Glitter eye shadow 16
17 Matte brown eye shadow Pigment Analysis Area 3 Area 4 Element Weight % Atomic % C O Na Mg Al Si K Ca Ti Cr Fe Element Weight % Atomic % C O Na Mg Al Si K Ca Ti Cr Fe Area 5 Element Weight % Atomic % C O Mg Al Si K Ca Ti Cr Fe
18 Glitter brown eye shadow Pigment Analysis Area 1 Element Weight % Atomic % C O Na Mg Al Si Cl Ag Ca Area 2 Element Weight % Atomic % C O Si Area 3 Element Weight % Atomic % C O Na Mg Al Si K Ti Fe
19 Regulatory Analysis Target Compound: Cocamide DEA The International Agency for Research on Cancer (IARC) lists cocamide DEA as an IARC Group 2B carcinogen. In June 2012, the California Office of Environmental Health Hazard Assessment added cocamide DEA to the California Proposition 65 (1986) list of chemicals known to cause cancer. Test articles #6: 3 Shampoos Analysis Method: QToF-LCMS 19
20 Regulatory Analysis Compound Tested: Positive ion MW (C 16 H 33 NO 3 + ) = Targeted Analysis by Extracted Ion Chromatograms (EICs) : Results: Cocamide DEA found in Blue Shampoo: 20
21 Regulatory Analysis Target Compounds: Primary Aromatic Amines (PAAs) Toxic effects of many PAAs are linked to bladder cancer, adverse effects on red cells, and skin sensitization. For these reasons, EU Cosmetic Regulations (EC) No. 1223/2009, many PAAs are prohibited for use in cosmetic products 21
22 Regulatory Analysis Analysis Method: Triple Quadrupole LCMS (QqQ-LCMS) Sample Preparation: The PAA mixture was diluted to 0.1 ng/ml to 1 ng/ml to construct calibration curves Results: ppt level detection and quantitaions of PAAs Peak ID Amine CAS RT Precursor Ion (m/z) Product Ion (m/z) R 2 1 o-anisidine o-toluidine o-tolidine ,3'-Dimethoxybenzidine Methoxy-5-methylaniline ,3'-Dimethyl-4,4'-diaminodiphenylmethane Thiodianiline Naphthylamine Aminobiphenyl IS Rhodamine B N.A Dichlorobenzidine Aminoazobenzene Methylene-bis-2-chloroaniline o-amino-azo-toluene
23 Summary Combine the power of all techniques, analytical chemistry could provide: Product deformulation through qualitative and quantitative analysis; Testing for batch-to-batch reproducibility, inconsistent performance, and other product problems; Determination the root cause of product failures; Inspection of pigments compositions; Analysis of product for regulatory requirements. Questions? 23
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