The Industrial Phase-Transfer Catalysis Experts

PTC Tip of the Month E-Newsletter

PTC Catalyst of the Month - August 2024

Polymerizable Quat Salts

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

There is learning value for process and product development chemists in a patent that describes polymerizable quat salts reported as cationic dopants to achieve a balance of physical properties in an adhesive in electro-optic applications. See McCullough, L.; Thomas, M.; Regan, T. (E Ink Corp) US Patent 12,031,065, 09-Jul-2024.

An electro-optic device consists of several layers with adhesive between them. The charge on the quat apparently participates in the electric field aspects of the device. However, if the charge migrates too much due to the electric field, this can cause non-uniform domains that lead to performance problems (see explanation below quoted from the patent).

If I understand correctly, one can achieve the right balance by dialing in certain side chains on the quats with the right polarity, chain length and monomer functional group(s) to enable the cationic dopant to function properly while preventing too much migration of the charge.

In this case, the best polymerizable quat salts were certain di-N-alkylated imidazolium salts.

The learning value for process and product development chemists is that we can achieve higher performance by customizing a specific balance of the physical availability and chemical properties of quat salts to meet specific needs. Since we have four chains on the quat, there are endless possibilities for designing this balance of physical and chemical properties.

Quote from the patent that describes the cationic quat dopants: “Without wishing to be bound by theory, dopants that exist in the adhesive layer as small molecules may diffuse and migrate in the layer and separate in their own phase or domain. This may create an adhesive layer having low and high conductivity domains and increasing the overall volume resistivity of the adhesive layer and, as a result, reducing the electro-optic switching performance of the electro-optic assembly. Such dopant separation is less likely to happen with polymeric dopants, which may be significantly less mobile and less likely to diffuse through the adhesive layer.”


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!).

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