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Uv Curable System Isom

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Uv Curable System Isom

  1. 1. Latent, UV-activated ROMP catalyst system Oleksandr (Sasha) Burtovyy1, Linda Zhang 1, Leah Langsdorf1, Alex Niemiec1, Dan Gastaldo1, Doug Skilskyj1, Krzysztof Skowerski2 and Larry Rhodes1 1 Promerus LLC, (Brecksville, OH USA) 2 Apeiron Synthesis, (Wrocław, Poland) UV light over 4 sec
  2. 2.  Global leader in Polycyclic Olefin (Norbornene) Technology  Product Development Group for Sumitomo Bakelite Co., Ltd. (SB)  Formerly BFGoodrich Electronic Materials (acquired by SB in 2001)  Includes monomer and polymer production  Main Application Areas:  Semiconductor Materials  High Performance Electronics and Display Materials  Membrane Materials  Emerging applications  ~30 Employees  Location  Brecksville, OH, USA 2 Promerus is a Leader in Cyclic Olefin Polymer (COP) Technology
  3. 3. 3 • Adhesion • Coefficient of Thermal Expansion • Elongation • Glass Transition Temperature • Modulus • Refractive Index • Surface Energy • Transparency • Impact resistance Our team of experts has the ability to tailor the functional groups of polymer properties. These include:
  4. 4. 4 Literature overview Photo-ROMP of cyclooctene 1. Latency – <1% conversion in 24h at 35 °C (in the dark) 2. Reactivity – 94% conversion in 1h irradiation in solution at 35 °C (350 nm) Y. Ginzburg, A. Anaby, Y. Vidavsky, C. E. Diesendruck, A. Ben-Asuly, I. Goldberg and N. G. Lemcoff. Organometallics 2011 PAG Photo-ROMP of cyclooctene 1. Latency – not reported 2. Reactivity – 95% conversion in 2h irradiation in solution (300 nm) B. K. Keitz and R. H. Grubbs. JACS 2009, 131, 2038 Photo-ROMP of DCPD 1. Latency – <5% conversion in 24h (in the dark) 2. Reactivity – 95% conversion in 15 min irradiation in solution (440 nm) C. Theunissen, M. A. Ashley and T. Rovis. JACS 2019, 141, 6791 Short Review: Or Eivgi and N. Gabriel Lemcoff. Synthesis 2018, 50, 49-53
  5. 5. 5 Current issues Issue Current status Requirements Latency Several days Weeks or months Photo-speed and conversion 10 min – 2h of irradiation Residual monomer < 1 min 100% reactive Solvent-less Use of solvent to improve solubility of catalyst and/or co- catalyst Neat formulation (no solvent)
  6. 6. 6 Schematic mechanism of our UV-activated ROMP catalyst system UV-only curable formulation Ru-catalyst active UV/N2 Photoactivator r.t.Ru-catalyst non-active UV/O2 Photoactivator ROMP No reaction Cyclic Olefin Monomer +
  7. 7. 7 Photoactivation mechanism X X¯ Ru-catalyst non-active Ru-catalyst active O2 X-O-O Photoactivator O2 O2 O2 O2 O2 Photoactivator + non-ionic nature X
  8. 8. 8 QUICK PHOTOCURE Fast process time Environment friendly No mixing needed Long pot-life Easy to transfer SOLVENT-LESS ONE-PART LATENT LOW VISCOSITY Advantages of Promerus’ unique system
  9. 9. 9 Our ROMP photopolymers have fast and complete cure after UV exposure light on at t=9.0 sec light off at t=13.0 sec 50% conversion at t=15 sec (∆t = 6 sec) * 99% conversion at t=39 sec (∆t = 30 sec)* Integral, %DSC, mW/mg * - calculated based on total heat released Area: 275 J/g Exposure conditions: 3 J/cm2 of 395 nm UV light in 4 sec at 30 °C
  10. 10. Our ROMP photopolymers have fast and complete cure after UV exposure 10 TGA of cured sample (after 3 J/cm2 in 4 sec) 10 °C/min ramp in N2
  11. 11. 11 One-part solvent-free formulations are stable and r.t. for weeks 0 50 100 150 200 250 300 0 5 10 15 20 25 30 35 40 45 50 0 5 10 15 20 Heatofreaction,J/g Viscosity,cP Time, days Latency
  12. 12. 12 Thermo-mechanical properties can be tuned by changing monomer compositions Elongation-to-break 100 % 3000 % Glass transition temperature - 20 °C 220 °C Young’s Modulus 0.001 GPa 2.0 GPa Impact resistance 20 J/m 800 J/m Formulation A: 200 % 122 °C (HDT - 91 °C) 0.9 GPa 600 J/m
  13. 13. 13 Digital Light Projection: Selective exposure to light by projectorFlashforge Hunter DLP 3D Printer Promerus new photopolymer formulations can be 3D-printed using DLP technology.
  14. 14. 14 Conclusions Promerus has developed a unique catalytic system that enables photo-polymerization of various cyclic olefins, which enables a new class of photopolymers for various applications. Our low-odor photocurable formulations offer several advantages, including low viscosity and long pot life resulting in polymers with a unique combination of high elongation-to- break, high Tg and high impact resistance. UV light over 4 sec

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