Competitive Intelligence through NMR Spectroscopy Applications in Detergents and Polymers
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1 Competitive Intelligence through NMR Spectroscopy Applications in Detergents and Polymers Kimberly L. Colson and Michelle A. Markus Bruker BioSpin Corporation, Billerica, MA USA
2 Competitive Intelligence What is this stuff? What is in these products? Assure-RMS using NMR spectroscopy is designed to answer the question! What is the composition of my competitor s products? Has it changed? Is my competitor infringing on my intellectual property? Competitive Edge Heads-up with new formulations How much of a specific ingredient does it have? What does it cost for my competitor to make their product? Cost, Performance What makes their product work/taste better? Hidden Ingredients Assure-RMS TM United States Patent 8,248,072
3 NMRs and Staff in Industry R&D Product properties Technical Expert in NMR Hands-on NMRs Development Customize screening approaches Technical Expert in NMR Production Perform screening in full automation Technician (not trained in NMR) R&D Production
4 Modern NMR Spectroscopy Magnets are Safer & Easier. Magnetic field (5 Gauss Line) at magnet leg Cryogen fills needed infrequently 5 Gauss Line NMRs are Smaller. Footprint ~ 7ft x 7ft Experts are not needed for screening. Full automation acquisition through analysis May be used in production facilities NMRs are affordable. Price range $150K $400K for 300 and 400MHz systems 400MHz NMR analysis of mixtures is information rich. Identification: Components, species Purity analysis Quantification Formulation/compositional analysis
5 Benefits of NMR in Competitive Intelligence Highly Reproducible (site to site) Chemical Fingerprint mixture analysis, product conformity, key components, impurities and adulterants Competitors Product 30 Replicate samples including preparation 6 different people prepared the samples 3 different 400MHz NMRs Detergent Model
6 Benefits of NMR in Competitive Intelligence Highly Reproducible (site to site) NMR Spectral Database Aloe vera Chemical Fingerprint mixture analysis, product conformity, key components, impurities and adulterants Chemically Specific - SBASE used, standard not needed daily SBASE Takes advantage of NMR s reproducibility (shift, coupling, intensity, shape)
7 Benefits of NMR in Competitive Intelligence Highly Reproducible (site to site) Chemical Fingerprint mixture analysis, product conformity, key components, impurities and adulterants Automated Quantification of chlorogenic acid in blueberry leaf extract using Line Fit Chemically Specific - SBASE used, standard not needed daily Absolute Quantification Area under an NMR signal is proportional to number of atoms giving rise to a signal Calibrated NMR, single-point long standing calibration Chlorogenic Acid Titration Curve
8 Assure Raw Material Screening What is Assure-RMS? Customizable software that fully automates NMR data acquisition and analysis of materials for targeted and nontargeted screening. Specification: Acquisition Analysis Reporting
9 Energy Drink Analysis by Assure-RMS 400 µl of energy drink and 200 µl of deuterated solvent Vortex/sonicate Transfer to NMR tube Sample Preparation Assure TM -RMS Equipped NMR System System Suitability Tests Quantification Calibration Automated Acquisition, Analysis Assure-RMS Report Targeted and Non- Targeted Screening of NMR spectra
10 Fully Automated Composition Analysis Energy Drinks From one 1 H NMR spectrum in full automation (~10min)
11 Assure-RMS Targeted Screening of Energy Drinks Monster Absolute Zero Red Bull M150
12 Competitive advantage: compositional analysis by NMR Product analysis to Evaluate product formulation. Check for particular ingredients. Quantitate components. Make global product comparisons. Useful for Full compositional analysis Competitive intelligence Intellectual property protection Quality control Automated Compositional Analysis Simplicity and automation Results in a few minutes using 1 H NMR Fully automated acquisition and analysis
13 Advantages of NMR for complex mixture analysis Highly reproducible Provides a chemical fingerprint Based on a crude extract, you can distinguish species and origin, impurities and adulterants. Identifies components Compare against reference spectra. Quantitative Area under an NMR signal is proportional to number of atoms giving rise to a signal A single-point measurement serves as a long-standing calibration. 82 samples acquired at Bruker represented by black diamonds 5 spectra acquired on one sample sent to different laboratories represented by red circles Markus et al., Planta Medica, :
14 Automated compositional analysis and quantification in just 2 minutes From a quick (2 minutes, 15 seconds) 1D 1 H spectrum of a detergent sample, we can get a lot of information: Identify components by comparison against a database of reference spectra (SBASE). Integrate peaks identified in components. Quantify individual components in the mixture. Automated fitting for quantification Compound Function Concentration (mm) sodium lauryl sulfate surfactant ethanol solvent glycerol solvent citric acid complexing agent Detergent spectrum compared to an Assure-RMS SBASE Matching, component identity, quantification, and analysis done with Assure-RMS!
15 Detecting specific ingredients: Triclosan, a controversial antibacterial 1 triclosan 2 2,3,7,8-Tetrachlorodibenzodioxin Triclosan (5-chloro-2-(2,4-dichlorophenoxy) phenol (1) widely used antibacterial found in dishwashing liquid, hand soaps, and body washes chlorinated aromatic compound, related to dioxin (2), a known toxin suggested to mimic steroid hormones known to accumulate in the environment Legislation has just been signed in Minnesota that bans triclosan after January 1, Additional information:
16 Triclosan is clearly identified by NMR Triclosan and other components can be quantitated in automation with Assure-RMS.
17 Understanding formulations: hypoallergenic versus original Consumers want products that have safe ingredients and are free of chemicals causing irritation. hypoallergenic formulations that eliminate unneccesary and potentially harmful chemicals added as dyes and fragrances white bottles of laundry detergent and clear bottles of dishwashing liquids on store shelves Dawn s product: pure essentials Similar ingredients to original scent, right down to the fragrance!
18 Is the hypoallergenic version always the same stuff? Palmolive pure+clear No! Different surfactants
19 It contains a botanical, but how much? Below the detection limit! detergent Aloe vera 1 H (ppm) Detection limit on the order of 100 M.
20 What are you paying for? Water! More water in Palmolive with orange extracts than Ultra original Ultra means 2X $3.39 for 25 oz per ounce Walgreens online $6.99 for 28 oz per ounce Walgreens online More product in Palmolive Ultra original than orange extracts!
21 Global product comparisons: testing for intellectual property infringement Using multivariate statistics to protect product intellectual property With enough representative samples, multivariate statistics can be used to compare sets of spectra. Principal component analysis (PCA), implemented with the AMIX software (Bruker BioSpin), was used to compare the brands Dawn and Palmolive. Dawn and Palmolive can be distinguished by PCA based on principal component 1 (PC1). Based on the loadings plot (not shown), PC1 corresponds to the surfactants present in the dishwashing liquid. This analysis potentially provides the means to identify different surfactants, providing a monitoring tool for protecting intellectual property.
22 Statistical model shows Dawn and Method are distinct products Method SIMCA model built in Assure-RMS Dawn Build a model for each brand using soft independent modeling of class analogies (SIMCA). Use the influence plot to compare the 1D 1 H NMR spectrum of Method dishwashing liquid against the model for Dawn. The sample Method is outside the 99% confidence limit (red zone) for the model of Dawn. Method is clearly a unique product.
23 Outlier detection in Assure-RMS identifies key differences Detected outliers can be compared against a reference spectral database to identify the components that differ. For this example, the outliers are in regions where surfactants appear. Based on comparison of the ingredient lists, this could reflect decyl + lauryl glucoside (in Method) versus sodium laureth sulfate (in Dawn).
24 Statistical model shows Dawn and Joy are very similar SIMCA model built in Assure-RMS Dawn Joy Usetheinfluenceplottocomparethe1D 1 H NMR spectrum of Joy dishwashing liquid with the model for Dawn. The sample Joy is within the 95% confidence limit (green zone) for the model of Dawn. Joy is closely related to Dawn. Both Dawn and Joy are made by Procter and Gamble!
25 Beyond dish liquid laundry detergent may contain citrate 1D 1 H spectrum of Tide Free & Gentle. Citrate is clearly identified in the spectrum, based on the SBASE match (not shown) and fit (shown as an inset), performed with Assure-RMS. Citrate is not listed as an ingredient!
26 Beyond dish liquid hand soap: Softsoap has two different base formulas Group 1 Group 2 Example of a personal care product: Softsoap Based on the 1D 1 H spectra, we can identify two different formulations of Softsoap. Group 2 contains unsaturated (olefinic) chains in the surfactants, while Group 1 does not. See the peaks from 7 to 5 ppm.
27 Applications to polymers Polymers represent another class of materials for NMR analysis. Details: Complex mixtures (like detergents) Broad lines (like the surfactant components) Compositional analysis Material-specific calculations
28 Analyzing Propylene 1- Butene polymers by NMR Propylene 1- Butene polymers are optically clear films and fine fibers having excellent low-temperature sealing properties and blocking resistance. Literature Propylene (P) Butene (B) ppm No pre-defined area for specific compound analysis ( targeted profiling) Not using any chemometric modelling to understand groups of samples ( nontargeted profiling) Understand the increase/decrease of predefined areas due to chemical reaction (custom calculation). User Defined Equation Methods! Chemical regions of interest Formulas for calculation of %mol
29 Developing an Assure-RMS method for Propylene 1- Butene polymers 1) Create a new method. 3) Input custom equation for analysis. Create a python script using your areas of interest as variables. Introduce new variables for output in report. 2) Select areas of interest. 4) Release method for NMR automated screening in IconNMR. Done! Select your nuclei ( 1 H, 13 C, etc.). Region integration/peak fit/intensity Noise factor Display threshold
30 Custom screening for polymers in Assure-RMS Poly(vinyl) Alcohol Characterization Commercial product #1 Commercial product #2 Manual calculation (average): ~88% PVOH ~12% PVAc Commercial product #3 PVOH % mol % % % PVAc % mol % % % Ethylene-Propylene Characterization Commercial product #1 Propylene % mol 97.9 % Ethylene % mol 2.1 % Manual Calculation Propylene: 97.9% Ethylene: 2.1%
31 Poloxamer characterization by NMR Poloxamers are excipients and surfactants, used in the cosmetic and pharmaceutical industries. Their properties depend on the oxypropylene to oxyethylene ratio. The NMR method from European Pharmacopeia 6.0: A1 = methyl groups (1.4 to 0.7ppm) A2 = CH 2 O Groups (3.8 to 3.2ppm) of a & b and CHO Groups of b % Oxyethylene = Poloxamer type A2 Ethylene oxide units (a) Propylene oxide units (b) Content of oxylethylene (%) A1 Ave. rel. mol. mass where = - 1 Assure Raw Material Screening Oxyethylene = 45.2%
32 Determining molar substitution of cyclodextrin Cyclodextrin is a cyclic oligosaccharide, used in the food, pharmaceutical, and chemical industries. European Pharmacopeia 5.0 specifies: The number of hydroxypropyl groups per anhydroglucose unit (molar substitution, MS) must be 0.40 MS 1.50 and within 10% of value stated on the label. A 1 = Methyl groups ( ppm) A 2 = Glycosidic protons ( ppm) C 42 H 70 O 35 (C 3 H 6 O) x with x = 7 MS Molar substitution = Degree of substitution = MS x 7
33 Tire rubber analysis EU Directive ISO for rubber analysis Rubber can be analyzed for polyaromatic hydrocarbons (PAH) content in full automation with Assure-RMS. The amount of bay region hydrogen must be <0.35% for tires as determined by NMR according to EU Directive ISO
34 Implementation of tire rubber analysis in Assure-RMS Define the regions for evaluation. Specify the chemical shift range for each region. Input the equation. Release the method for automation. Analyze samples in full automation with Assure-RMS!
35 Conclusions NMR is a powerful technique for analyzing complex mixtures. Identification of components by comparison against a reference spectral database Identification of materials by testing against a statistical model based on validated samples Quantification of components NMR can be applied to: Compositional analysis Competitive intelligence IP protection Quality control Assure-RMS provides tools to automate NMR analysis.
36 Thank you for your attention! Questions? Contact Copyright 2014 Bruker Corporation. All rights reserved.
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