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.  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
• 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
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
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
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
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
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
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. 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
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
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
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
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