The Industrial Phase-Transfer Catalysis Experts

PTC Tip of the Month E-Newsletter

PTC Catalyst of the Month - April 2024

Quat Salts Used with Epoxy Resins and Curing Agents in Semiconductor Production

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

This month we seem to have more patent activity than usual in the area of quats with epoxides used in the semiconductor industry.

This publication, Matsuura, Y.; Sato, A.; Yamazawa, T. (Namics Corporation) US Patent Application Publication No 2024/0132714, 25-Apr-2024, describes the use of a variety of quat salts in a system that I will attempt to explain according to my novice understanding that may be incorrect.

If I understand correctly (which might not be the case), the goal of this technology is to ensure that the electrode “bump” of a semiconductor is accessible while protecting the rest of the semiconductor surface. For this purpose, a cured epoxy resin and a “filler” (like silica) is used to coat the semiconductor with the electrode protruding for connection to another component.

The epoxy resin is cured with a curing agent, typically containing an amine.

The patent claims that the presence of an ionic compound (chosen from a group with many quat salts) is crucial to ensure uniform distribution of the epoxy resin and filler but the patent does not explain why the ionic compound works. I speculate that the anion of the ionic compound serves as an initiator for the curing of the epoxy resin by the amine-based curing agent.

Regardless of whether this speculative explanation is correct, the ionic compounds that are explicitly claimed in Claim 8 contain quat cations familiar to us as PTC practitioners and they are:
• Methyltrioctylammonium tosylate
• Methyltrioctylammonium hexafluorophosphate
• Methyltrioctylammonium imidodisulfuryl fluoride
• Methyltrioctylammonium bis(trifluoromethanesulfonyl)imide
• Tributyldodecylphosphonium tosylate
• Tributyldodecylphosphonium dodecylbenzenesulfonate
• Tributylmethylammonium bis(trifluoromethanesulfonyl)imide
• Tetrabutylammonium hexafluorophosphate
• 1-Butyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide
• Tributyldodecylphosphonium bis(trifluoromethanesulfonyl)imide
• 1-Hexyl-4-methylpyridinium bis(trifluoromethanesulfonyl)imide
• Trimethylpropylammonium bis(trifluoromethanesulfonyl)imide
• 4-(2-Ethoxyethyl)-4-methylmorpholinium bis(trifluoromethanesulfonyl)imide
• 1-Butyl-3-dodecylimidazolium bis(trifluoromethanesulfonyl)imide
• N-Oleyl-N,N-di(2-hydroxyethyl)-N-methylammonium bis(trifluoromethanesulfonyl)imide
• Tributyl[3-(trimethoxysilyl)propyl]phosphonium 1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]methanesulfonamide


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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