Patent GB-801710-A (GB)
Title: N-polyoxyalkylene derivatives of heterocyclic amines
IPC: C11D1/88
Filed: 1957-05-23
Abstract: The invention comprises N-polyoxyalkylene derivatives of piperidine and pyrrolidine having the general formula R-(Y-O-)-xH wherein R represents piperidyl or pyrrolidyl, each Y represents an ethylene, propylene or butylene radical and x is an integer of at least 6. They may be prepared by reacting the amine with one or more appropriate alkylene oxides in the amount necessary to introduce the desired numbers of oxyalkylene units. The alkylene oxide may be introduced portionwise.  Products containing mixed oxyalkylene units may be prepared by reacting the different alkylene oxides simultaneously or successively. Reaction temperatures of 75-175 DEG C. and pressures of 10-175 lbs./sq. inch may be used.  Catalysts such as sodium or potassium hydroxide may be present.  The products are useful as wetting, emulsifying or dispersing agents and may be used, e.g. with a finely divided solid or liquid carrier, for insecticidal or germicidal purposes (see Group VI).  Examples describe the preparation of polyoxy alkylene derivatives from each amine and (1) 10 mols. of ethylene oxide, (2) 10-11 mols. of propylene oxide, (3) 9-10 mols. of 1:2-epoxy butane (reacted in two portions) and (4) 10 mols. of an equimolar mixture of ethylene and propylene oxides and from piperidine and 30 mols. of ethylene oxide (reacted in two portions) or, in two separate stages, 10 mols. of 1:2-epoxy butane and 10 mols. of ethylene oxide.  Another specified alkylene oxide is 2:3-epoxy butane.ALSO:The invention comprises N-polyoxyalkylene derivatives of piperidine and pyrrolidine having the general formula R-(Y-O-)-a H, wherein R represents piperidyl or pyrrolidyl, each Y represents an ethylene, propylene or butylene radical and x is an integer not less than 6.  They may be prepared by reacting the amine with one or more appropriate alkylene oxides in amount sufficient to introduce the required number of oxyalkylene units.  Reaction may be effected at 75-175 DEG  C. under a pressure of 10-175 lbs./sq. inch, if desired in the presence of a catalyst such as sodium or potassium hydroxide.  The alkylene oxide may be reacted portionwise.  Products containing mixed oxyalkylene units may be prepared by introducing the different alkylene oxides simultaneously or successively into the reaction mixture.  The products are useful as wetting, emulsifying and dispersing agents and in the control of insects and bactericidal organisms (see Group VI).  Examples describe the preparation of polyoxyalkylene derivatives from each amine and (1) 10 mols. of ethylene oxide, (2) 10-11 mols. of propylene oxide, (3) 9-10 mols. of 1:2-epoxy butane (reacted in two portions) and (4) 10 mols. of an equimolar mixture of ethylene and propylene oxides and from piperidine and 30 mols. of ethylene oxide (reacted in two portions) or, in two separate reaction stages, 10 mols. 1:2-epoxy butane and 10 mols. ethylene oxide.  Another specified alkylene oxide is 2:3-epoxy butane.ALSO:Insecticidal and germicidal compositions comprise, as the active ingredient, an N-poly-oxyalkylene derivative of piperidine or pyrrolidine having the general formula R-(Y-O-)-xH wherein R represents piperidyl or pyrrolidyl, each Y represents an ethylene, propylene or butylene radical and x is an integer of at least 6. The compounds may be used in admixture with a finely divided solid or liquid carrier in the control of, for example, aphids, Aspergillus terreus, Salmonella typhosa, Staphylococcus aureus and Rhizopus nigricans.  Specified compounds are derived from piperidine or pyrrolidine and 10 mols. ethylene oxide, 10-11 mols. of propylene oxide, 9-10 mols. of 1 : 2-epoxy-butane or 10 mols. of an equimolar mixture of ethylene and propylene oxides and from piperidine and either 30 mols. of ethylene oxide or 10 mols. of 1 : 2-epoxy butane and thereafter 10 mols. of ethylene oxide. The derivatives containing 2 : 3-epoxy butylene radicals are also referred to.  The preparation of the active compounds is given (see Group IV(b)).