Method for the synthesis of quaternary ammonium salts
AssigneeNippon Paint Co., Ltd.
InventorsShinji Nakano, Takao Morimoto, Takeshi Endo
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Abstract
Provided is a convenient method for synthesizing quaternary ammonium salts which are useful as curing catalysts for one-part thermosetting resin compositions which maintain storage stability at room temperature. The ammonium salts are synthesized by direct reaction of a benzyl alcohol or a benzyl alkyl ether optionally having on the benzene ring and/or at .alpha.-position one or more substituent groups inert to the intended reaction, with a corresponding strong-acid salt of a tertiary amine.
Claims11
A method for synthesizing a quaternary ammonium salt comprising
- reacting, under effective conditions, a strong-acid salt of a tertiary amine with a benzyl alcohol or a benzyl alkyl ether in which the alkyl group is a C.sub.1 -C.sub.4 saturated hydrocarbon group, optionally having on the benzene ring, at .alpha.-position or both, one or more substituent groups inert to the intended reaction and
- recovering said quaternary ammonium salt from the reaction mixture.
A method for synthesizing an N-benzylpyridinium salt which comprises reacting a benzyl alcohol of the formula:
- ##STR7## wherein R.sub.1, R.sub.2 and R.sub.3, independently of one another, denote hydrogen, halogen, alkyl, alkoxy, nitro, acyl, cyano or alkoxycarbonyl and R.sub.4 and R.sub.5 independently of one another denote hydrogen, halogen or alkyl, or a C.sub.1 -C.sub.4 alkyl ether of said benzyl alcohol,
- with an acid addition salt of HAsF.sub.6, HSbF.sub.6, HBF.sub.4, HPF.sub.6 or HCF.sub.3 SO.sub.4 and a pyridine of the formula ##STR8## wherein R.sub.6 and R.sub.10 independently of one another denote hydrogen, halogen, alkyl, alkoxy, nitro, acyl, cyano or alkoxycarbonyl,
- in an aprotic solvent under conditions effective to quaternize said pyridine salt with said benzyl alcohol or alkyl ether thereof.
A method for synthesizing an N-benzylanilinium salt which comprises reacting a benzyl alcohol of the formula:
- ##STR9## wherein R.sub.1, R.sub.2 and R.sub.3, independently of one another, denote hydrogen, halogen, alkyl, alkoxy, nitro, acyl, cyano or alkoxycarbonyl and R.sub.4 and R.sub.5 independently of one another denote hydrogen, halogen or alkyl, or a C.sub.1 -C.sub.4 alkyl ether of said benzyl alcohol,
- with an acid addition salt of HAsF.sub.6, HSbF.sub.6, HBF.sub.4, HPF.sub.6 or HCF.sub.3 SO.sub.4 and an aniline derivative of the formula ##STR10## wherein R.sub.7 and R.sub.8 independently of one another denote alkyl or alkenyl, and R.sub.9 denotes hydrogen, halogen, alkyl, alkoxy, nitro, acyl, cyano or alkoxycarbonyl,
- in an aprotic solvent under conditions effective to quaternize said pyridine salt with said benzyl alcohol or alkyl ether thereof.
Dependencies are inferred from the claim text.