Inks, Lubricants, Adhesives, Coatings How To Find Your Competitor s Recipe!
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1 Inks, Lubricants, Adhesives, Coatings How To Find Your Competitor s Recipe! July 25, 2012
2 Presenters Tracy Phillpott Senior Applications Chemist Spectra Analysis Instruments, Inc. Ming Zhou, PhD Director of Applications Engineering Spectra Analysis Instruments, Inc.
3 Outline Introduction: GPC-IR Hyphenated Technology DiscovIR System: Instrumentation & Features GPC-IR to De-Formulate Complex Polymer Mixtures Case #1: De-Formulate a Hot Melt Adhesive Case #2: De-Formulate a Conductive Ink Case #3: De-Formulate a UV Curable Coating Case #4: De-Formulate Polymeric Additives in Lubricant Oil Summary
4 Combination of Single Parameters Tools: Hyphenated Systems Separation System and Detection System Bundling two analytical techniques to enable the characterization of the polymeric system along two axes Size ( SEC/GPC) for the molecular weight distribution Composition for the architecture
5 GPC-IR Hyphenated System: Principle and Information Output GPC for the Separation of the Polymers by MW or Size Infrared Spectroscopy for Compositional Information
6 DiscovIR-GPC GPC-IR Hyphenated System
7 Principle of a GPC-IR Hyphenated System GPC Chromatography eluant is nebulized and stripped of mobile phase in the Hyphen Analytes deposited as a track on a rotating ZeSn disk. Track passes through IR energy beam of built-in interferometer. A time-ordered set of IR spectra are captured as a data file set.
8 Hyphen: A Proprietary Desolvation Technology From LC Thermal Nebulization N2 Addition Cyclone Evaporator Cyclone Evaporator Air Cooled Condenser Chilled Condenser Patent pending: PCT/US2007/ Particle Stream to DiscovIR Waste Solvent
9 The Thermal Nebulization The thin-wall stainless steel capillary tube nebulizer is regulated to evaporate approximately half the solvent (electric heating). Solvent expansion upon conversion to vapor increases the nebulizer back pressure and create a high-speed jet of micrometer-sized liquid droplets that contain all the solute. Gradients are acceptable as it is a self regulating system (gradient changes monitored by changes in electrical resistance).
10 Inside the Cyclone Evaporator Centrifugal force holds the droplets (solute) near the cyclone wall. Just before the droplet goes to dryness, its volume to surface ratio becomes small enough that it is dragged out of the cavity by the exiting solvent vapor. Evaporative cooling protects the solute from both evaporation and degradation by limiting the maximum solute temperature to the solvent boiling point. The solvent boiling point is reduced by operating the cyclone in a vacuum.
11 At the Condensers After ejection from the cyclone, solvent vapor is removed by diffusion to, and condensation on, the cooled condenser walls. Stokes drag from the nitrogen gas maintains the dried droplets in an aerosol suspension and limits their loss by diffusion to the condenser walls. The condenser consists of an air cooled stage followed by a Peltier cooled stage. The condensed solvent is collected in a waste bottle. Series of Condensers
12 Proprietary Deposition Technology Solid phase deposition for reproducible and higher quality spectra (compare to liquid or gas flow cell) Entire mid IR range Cryogenically cooled Under vacuum No CO 2 or H 2 O interference IR scan every 0.4 sec Transmission IR analysis is done on the solid deposit. Better S/N ratio Allows for rescan Use of ZnSe disk for substrate Disc is large enough for unattended overnight runs Easy clean up Ten hours worth of chromatographic data Auto sampler compatible
13 Absorbance Characterization of Polymers Using GPC-IR IR Spectra CH2 A chromatogram reflects the elution distribution of a particular chemical structure. HIGH MW LOW MW Wavenumber, cm-1 C=O C-O CH3 CH2 SMALL MOLECULES POLYMER C COPOLYMER A-B GPC Elution Time, min MW =f(elution Time) Data format is a time-ordered set of IR spectra. Instrument software extracts spectral band chromatograms from a data set of spectra.
14 Outline Introduction: GPC-IR Hyphenated Technology DiscovIR System: Instrumentation & Features GPC-IR to De-Formulate Complex Polymer Mixtures Case #1: De-Formulate a Hot Melt Adhesive Case #2: De-Formulate a Conductive Ink Case #3: De-Formulate a UV Curable Coating Case #4: De-Formulate Polymeric Additives in Lubricant Oil Summary
15 Characterizing Polymer Mixtures by GPC (Size) or IR (Composition) GPC: Chromatographic Separation of Components IR: Fingerprinting of Chemical Compositions Provides size distribution (MWD). No identification of polymers additives Unambiguous identification only practical for single species. Compounded IR spectra for mixtures. GPC only: 2 or 3 peaks? IR only: Compounded spectra B? C A
16 absorbance Case #1: De-Formulate a Hot-Melt Adhesive Polymer Mixture: GPC-IR Data 3D View Competitive study of a hot-melt adhesive: for cost and margin structure comparison. for technical evaluation IR Wavenumber, cm C=O GPC Elution Time, min
17 GPC-IR De-Formulation of the Adhesive Polymer Mixture A B? C Max (Band) Chromatogram at 2929 cm -1 B Selected Band Chromatogram at 1724 cm -1 A
18 GPC-IR Database Search to Identify Peak A at 10 minutes as EVA Polymer -CH A C=O 1724
19 GPC-IR to Identify Components C & B by Spectral Subtraction Component C Paraffin Component B Glycerol Rosin Ester
20 GPC Confirmation of the De-Formulated Components with Known Standards A, B & C A B C A B C
21 Case #2: De-Formulate a Flexible Conductive Ink by GPC-IR Silver ink paste filled with Ag particles (~80% Wt) Designed to screen print flexible circuitry such as membrane switches Extremely flexible after curing at 150 C for 30 minutes Very conductive even under 20x folding / crease stress tests (ASTM F1683). 5 times better than the next competitor Understand the unique formulation technology Deformulate the complex polymer system
22 De-Formulating the Conductive Ink GPC-IR Chromatogram Column: 2 x Jordigel DVB Mixed Bed Mobile Phase: THF at 1.0 ml/min Sample Conc.:~5 mg/ml in THF Injection Volume: 60 μl IR Detector Res.: 8 cm -1 ZnSe Disk Temp.: -10 C Cyclone Temp.: 130 C Condenser Temp.: 15 C Disk Speed: 12 mm/min
23 Stacked IR Spectra of Components A, B, C at Different GPC Times (~ MWD Centers) NH
24 Commercial IR Database Search (FDM & Thermo) for Polymer A (Red): Polyester Suppliers Index % Match Compound Name Library Amoco Resin PE-350 Polyester Coatings Technology Dynapol LH-812 Polyester Coatings Technology Vitel VPE-222F Polyester Coatings Technology Dynapol L-411 Coatings Technology Vitel PE-200 Coatings Technology
25 Commercial IR Database Search (FDM & Thermo) for Component B (Blue): Polyurethane Supplier NH OH Index % Match Compound Name Spensol L-53 UROTUF L-53 Polyurethane Polyester Polyol Polycaprolactone Polyester Polyol UCAR Cyracure UVR-6351
26 Commercial IR Database Search (FDM & Thermo) for Component C (Red): Cross-linker Supplier Index % Match Compound Name Desmodur LS-2800, CAS# , MW 766, Cross-linking Agent Caffeine; 1,3,7-Trimethylxanthine Monophenylbutazone Betulinic acid; 3-Hydroxylup-20(29)-en-28-oic acid Spenlite M-27
27 Reverse-Engineering the Conductive Ink by GPC-IR Deformulation C C: Desmodur LS-2800 Ketoxime blocked HDI trimer Latent cross-linking agent B Curing (150 o C / 30 min) A De-blocked C cross-linking with Polymer B Chains Interpenetrating with Polymer A Lock Ag fillers in place to form conductive circuitry Super flexibility & elasticity Superior end-use properties
28 Case #3: De-Formulate a UV Curable Coating by HPLC-IR Column: Eclipse XDB-C18, 4.6 x150mm Mobile Phase: A&B at 1.0 ml/min Solvent A: 0.1% Formic Acid in Water Solvent B: 0.1% Formic Acid in MeOH Gradient: Time/%B: 0/1, 30/95, 40/95 Sample Conc.:10 mg/ml in MeOH Injection Volume: 75 μl IR Detector Res.: 8 cm -1 Nebulizer Power: 18 watts ZnSe Disk Temp.: -10 C Cyclone Temp.: 180 C Condenser Temp.: 5 C Disk Speed: 3 mm/min A B C
29 Commercial IR Database Search for Component A (Blue) Index % Match Compound Name Library Ethyl Acrylate Coatings Technology (Thermo) Hydroxylpropyl Acrylate Coatings Technology (Thermo) ,6-Hexanediol Diacrylate Coatings Technology (Thermo)
30 Commercial IR Database Search for Component B (Blue) Index % Match Compound Name Library Trimethylolpropane Triacrylate Coatings Technology (Thermo) Dipentaerythritol Triacrylate Coatings Technology (Thermo) Pentaerythritol Triacrylate Coatings Technology (Thermo)
31 IR Database Search for Component C (Aqua): Photomer 6022 Index % Match Compound Name Library Photomer 6022: Coatings Technology (Thermo) Urethane Acrylate Oligmer Trimethylolpropane Triacrylate Coatings Technology (Thermo) Pentaerythritol Triacrylate Coatings Technology (Thermo)
32 Case #4: De-Formulate Lubricant Additives in SAE 15W-40 Motor Oil Identification of additives like stabilizers, viscosity modifiers, fungicides, etc. Stability: ageing & failure analysis Additive Y 12 Additive X GPC Elution Time (Min. & MW) Wavenumber, cm -1 Low MW mineral oil (~85%) diverted after 12.2 min
33 De-Formulation of Motor Oil Additive X at RT 9.2 Minutes Shell Rotella T Heavy Duty 15W minute eluant wavenumber, cm-1 IR database search: Styrene-Acrylate Copolymer
34 De-Formulation of Motor Oil Additive Y at RT 12 Minutes Shell Rotella T Heavy Duty 15W minute eluant wavenumber, cm-1 IR database search: Polyisobutenyl Succinimide (PIBS)
35 Additive De-Formulation in Motor Oil Lubricant by GPC-IR De-formulated polymeric additives X & Y in motor oil lubricant Additive X at retention time 9.2 minutes Narrow MW distribution ~ average 600K (GPC) Styrene-Acrylate copolymer (IR database search) Viscosity Index improver Additive Y at retention time minutes Broad MW range: 8-30K (GPC) Polyisobutenyl Succinimide (PIBS) (IR database search) Dispersant for metal particles Polymer degradation study Analyze polymer breakdown or cross-linking by GPC Detect oxidized intermediates by IR Oil change schedule
36 GPC-IR to Characterize Polymer Stability in Lubricant Oils X0 ID? 170C G0: 0 hr G12: 12 hr G24: 24 hr G36: 36 hr G48: 48 hr X2 X1 X3 Y0 X4 Note: Base oil was diverted at 25 min.
37 In-House IR Database Search for Polymeric Additive X0 (Red): SEB Copolymer
38 Compositional Changes of Polymeric Additive X0 X1, X2, X3 & X4 by Oxidation Oxirane 170C G0: 0 hr G12: 12 hr G24: 24 hr G36: 36 hr G48: 48 hr Ether
39 GPC-IR to Characterize Polymer Degradation in Oils X0 ID: SEB 170C G0: 0 hr G12: 12 hr G24: 24 hr G36: 36 hr G48: 48 hr X2 X1 X3 Oxidizing Ethers ( cm -1 ) Oxiranes (806 cm -1 ) Y0 X4
40 Polymeric Additive X0 Oxidized to X4 and Breakdown to Z4 Oxirane 170C G0: 0 hr X0 G48: 48 hr X4 dotted line Z4 C=O Ether
41 GPC-IR to Characterize Polymer Degradation in Oils 170C G0: 0 hr G12: 12 hr G24: 24 hr G36: 36 hr G48: 48 hr X2 X0 ID: SEB X1 X3 Oxidizing Ethers Oxiranes Y0 Oxidative Breakdown Carbonyls Oxiranes Ethers X4
42 Summary: GPC-IR to De-Formulate Complex Polymer Mixtures GPC-IR is well adapted for the de-formulation of complex polymer systems Separation of all the components of a mixture (polymer and small molecules) Detection of each component by IR (solid phase transmission) Identification by IR database search (commercial & proprietary databases) Useful: For competitive analysis / IP protection To find specific raw material supplier or qualify a second supplier For problem solving / trouble shooting / contamination analysis / degradation Applicable to coatings, adhesives, inks, sealants, elastomers, plastics, rubbers, composites, biopolymers
43 Summary: GPC-IR to De-Formulate Complex Polymer Systems GPC Separation IR Spectra X? Y? Z? IR ID A-B Copolymer C Polymer Additive IR Database Product Name Product # Brand Name Search & Supplier & Supplier & Supplier
44 Summary: GPC-IR to Characterize Compositional / Structural Variations of Copolymers across MWD A/B Ratios IR Spectra A B A-B C Composition Supplier-to-Supplier Built-in Feature / Difference for ID Drifts & Lot-to-Lot Variations Copolymer R&D / Process Control Variations & Incoming QC for Users
45 Summary: GPC-IR to Characterize Copolymer Degradation from Ageing / Processing A/B Ratios Degradation A-B C Degradants Degradation Loss of Functional Group A (Reduced A/B Ratios) Polymer Breakdown ( Lower MW Degradants) Cross-linking ( Higher MW with New Functional Groups) Confirm No Degradation / Stability Study
46 Application Notes Deformulating Polymeric Ink Formula by GPC-IR Technology Characterization of a Hot-Melt Adhesive by LC-IR Lubricants Analysis Analysis of Polymer Blends by GPC-FTIR Polymer Characterization by Combined Chromatography- Infrared Spectroscopy (article published in LC-GC)
47 Spectra Analysis Instruments, Inc. Ming Zhou, PhD Director of Applications Engineering Tracy Phillpott Senior Applications Chemist Tom Kearney Vice President of Sales
48
49 Comparison of Max Band Chromatogram (Black) and Selected Band Chromatograms Max Band Default At 1730 cm -1 A Band 1510 cm -1 Band 1690 cm -1 Band 730 cm -1 B C Elution Time (Min.)
50 Polymer & Small Molecule Analysis by GPC-IR for ABS Plastic w/ No Extraction Step GPC-IR chromatogram (Blue) for ABS sample and ratio plot of Nitrile/Styrene (2240 cm-1/1495 cm-1). Polymers Identification Compositional Variations Small Molecules Additives Impurities Degradants
51 GPC-IR Applications: Model Cases De-Formulate Complex Polymer Mixtures: PolyX + Poly(A-B) + Additives PolyX + PolyY + Poly(A-B-C) + Additives Characterize Copolymer Compositions across MWD: Poly(A-B), Poly(A-B-C), Poly(A-B-C-D), Polymer Blend Ratio Analysis across MWD: PolyX + PolyY Polymer Additive Analysis by HPLC-IR: Add. (SM or PolyX) Analyze Polymer Changes: Degradation or Modification 51
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