The Industrial Phase-Transfer Catalysis Experts

PTC Tip of the Month E-Newsletter

PTC Tip of the Month - January 2018

Phase-Transfer Catalysts Improve Polymer Performance for Epoxy Resins and Nitrile Rubber

By Marc Halpern, the leading expert in industrial phase-transfer catalysis.

Improve Polymer Performance for Epoxy Resins

US Patent 9,868,751 shows that when using a variety of curing catalysts containing tetraphenyl phosphonium salts of anilide anions (salicylanilide derivative for example) for polymerizing epoxy resins with curing agents (phenolics such as novolacs) at 95 deg C, for encapsulating semiconductor devices, much better performance is obtained than when using non-phosphonium curing agents such as triphenyl phosphine.

The better performance includes higher flowability, higher stability, lower shrinkage and higher curing rates at lower temperatures, achieved in shorter curing times.

Although not addressed in the patent, the higher performance may be related to the combination of having an anionic curing agent paired with a thermally stable quaternary phosphonium cation.

Kim, M.; Kwon, K.; Lee, D.; Chung, J.; Cheon, J.; Choi, J.; (Samsung SDI CO., LTD.) US Patent 9,868,751, 16-Jan-2018

Improve Polymer Performance for Nitrile Rubber

US Patent 9,868,806 describes technology for producing nitrile rubber that is vulcanized without using sulfur. The rubber is a butadiene (58.5 parts)-acrylonitrile (35.5 parts) polymer containing glycidyl methacrylate (6 parts) for crosslinking. When using tetrabutylammonium bromide (4 parts), without the addition of heavy metal compounds, it is possible to achieve a high elongation at break and tensile strength.

Although not addressed in the patent, it is possible that the mechanism is ring opening of the epoxide by the bromide of TBAB followed by continued reaction of the resulting epoxide (addition reaction to an unsaturated bond).

Brandau, S.; Klimpel, M.; Magg, H.; Welle, A.; (Arlanxeo Deutschland GmbH) US Patent 9,868,806, 16-Jan-2018

Contact Marc Halpern of PTC Organics to integrate your expertise and commercial goals with PTC Organics’ highly specialized expertise in industrial phase-transfer catalysis to achieve higher process performance.

About Marc Halpern

Marc Halpern

Dr. Halpern is founder and president of PTC Organics, Inc., the only company dedicated exclusively to developing low-cost high-performance green chemistry processes for the manufacture of organic chemicals using Phase Transfer Catalysis. Dr. Halpern has innovated PTC breakthroughs for pharmaceuticals, agrochemicals, petrochemicals, monomers, polymers, flavors & fragrances, dyes & pigments and solvents. Dr. Halpern has provided PTC services on-site at more than 260 industrial process R&D departments in 37 countries and has helped chemical companies save > $200 million. Dr. Halpern co-authored five books including the best-selling “Phase-Transfer Catalysis: Fundamentals, Applications and Industrial Perspectives” and has presented the 2-day course “Practical Phase-Transfer Catalysis” at 50 locations in the US, Europe and Asia.

Dr. Halpern founded the journal “Industrial Phase-Transfer Catalysis” and “The PTC Tip of the Month” enjoyed by 2,100 qualified subscribers, now beyond 130 issues. In 2014, Dr. Halpern is celebrating his 30th year in the chemical industry, including serving as a process chemist at Dow Chemical, a supervisor of process chemistry at ICI, Director of R&D at Sybron Chemicals and founder and president of PTC Organics Inc. (15 years) and PTC Communications Inc. (20 years). Dr. Halpern also co-founded PTC Interface Inc. in 1989 and PTC Value Recovery Inc. in 1999. His academic breakthroughs include the PTC pKa Guidelines, the q-value for quat accessibility and he has achieved industrial PTC breakthroughs for a dozen strong base reactions as well as esterifications, transesterifications, epoxidations and chloromethylations plus contributed to more than 100 other industrial PTC process development projects.

Dr. Halpern has dedicated his adult life to his family and to phase-transfer catalysis (in that order!).

Leave a Reply

Your email address will not be published. Required fields are marked *

PTC Course - In-House

Learn to choose
PTC process conditions
LIKE AN EXPERT!

Learn More