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 the synthesis of quaternary ammonium sulfonate compounds which are useful as curing catalysts for one-part thermosetting resin compositions which maintain storage stability at room temperature. The compounds are synthesized by subjecting in one step a benzyl alcohol optionally having on the benzene ring and/or the .alpha.-position one or more substituent groups to reaction with a corresponding tertiary amine and an organic sulfonic acid chloride.
Claims8
A method for synthesizing an N-benzylpyridinium sulfonate which comprises reacting in one step a benzyl alcohol of the formula:
- ##STR4## wherein R.sub.1, R.sub.2 and R.sub.3 independently of one another denote hydrogen, hydroxyl, halogen, alkyl, alkoxy, nitro, amino, alkylamino, acyl, cyano, alkoxycarbonyl or carbamoyl, and R.sub.4 and R.sub.5 independently of one another denote hydrogen, halogen or alkyl,
- with a benzene- or naphthalenesulfonyl chloride optionally substituted with one or more alkyl groups, and
- a pyridine of the formula:
- ##STR5## wherein R.sub.6 and R.sub.10 independently of one another denote hydrogen, hydroxyl, halogen, alkyl, alkoxy, nitro, amino, alkylamino, acyl, cyano, alkoxycarbonyl or carbamoyl,
- in the presence of an acid-binding agent to produce an N-benzylpyridinium sulfonate.
A method for synthesizing an N-benzylanilinium sulfonate which comprises reacting in one step a benzyl alcohol of the formula:
- ##STR6## wherein R.sub.1, R.sub.2 and R.sub.3 independently of one another denote hydrogen, hydroxyl, halogen, alkyl, alkoxy, nitro, amino, alkylamino, acyl, cyano, alkoxycarbonyl or carbamoyl, and R.sub.4 and R.sub.5 independently of one another denote hydrogen, halogen or alkyl, with
- a benzene- or naphthalenesulfonyl chloride, and
- an aniline derivative of the formula ##STR7## wherein R.sub.7 and R.sub.8 independently of one another denote alkyl or alkenyl, and R.sub.9 denotes hydrogen, hydroxyl, halogen, alkyl, alkoxy, nitro, amino, alkylamino, acyl, cyano, alkoxycarbonyl or carbamoyl,
- in the presence of an acid-binding agent to produce an N-benzylanilinium sulfonate.
Dependencies are inferred from the claim text.