Mitsubishi Gas Chemical Company, Inc.

Mutsuhiko Takeda

Akitoshi Sugio

Tomotaka Furusawa

Katsumasa Tanaka

Toshikazu Umemura

Minoru Kakuda

Akira Amemiya

Masafumi Shimpo

Fumiya Zaima

Isao Hagiwara

Kiyoshi Yoshida

Tadashi Kunii

Shuzabu Sakaguchi

Takeo Suzumori

Kiyokazu Kawaguchi

Yoshihiro Ono

Tetsuya Abe

Yasumasa Norisue

Masamichi Mizukami

Masaharu Kimura

Michio Ohba

Masanori Furukawa

Makoto Mizutani

Isamu Masumoto

Yoshiharu Ohtsuki

Akira Amamiya

Toshikazu Umenura

Noriyasu Nakao

Kazuyoshi Taka

Toshie Takahashi

An insect-proofing agent comprising 1,3,5-trioxane as an active ingredient is disclosed. This insect-proofing agent has a high insect-proofing action and gives no irritating odor, and the insect-proofing agent is not toxic to human bodies and has a high safety. Furthermore, this insect-proofing agent causes no discoloration in metallic substance such as silver thread, gold threads and spangles used for clothing decoration. This insect-proofing agent is effectively applied in the form of a solid preparation, an aqueous solution or an organic solvent solution.

Moth-proofing method using trioxane as sole active

Novel methylthiophenol derivatives of the formula (I') and of the formula (IV) and processes for producing said derivatives ##STR1## wherein R is a tert-butyloxy group, a tert-amyloxy group, a p-methoxybenzyloxy group, a 2-(trimethylsilyl)ethoxy group, a 1-adamantyloxy group, a bornyloxy group, or an isobornyloxy group.

Methylthiophenol derivatives and p-methylthiophenyl chloroformates and

A process for producing sulfonium compounds represented by the general formula (III) which comprises reacting alkylthiophenol derivatives represented by the general formula (I) and dialkyl sulfate represented by the general formula (II).

Process for production of sulfonium compounds

By incorporating a liquid or solid silicone or paraffin into 1,3,5-trioxane, agglomeration of trioxane particles and adhesion of the trioxane to a machine wall or the like can be prevented. The silicone or paraffin is used in an amount of 0.003 to 1% by weight.

Trioxane composition and insect-proofing agent

Disclosed is process for producing a sulfonium compound of the general formula (III), comprising reacting alkylthiophenol derivative of the general formula (I) and dialkyl sulfate of the general formula (II) in the presence of at least one inorganic compound selected from the group consisting of alkali metal carbonate, alkali metal hydrogencarbonate, alkaline earth metal hydroxide, alkaline earth metal carbonate, and oxides of Group II metals of the Periodic Table. ##STR1## wherein all the symbols are as defined in the appended claims.

Process for production of sulfonium compounds and novel methylthiphenol

Disclosed is a composition comprising trioxane and an assistant aiding in the insect-proofing action of trioxane or controlling its vapor pressure.

Disclosed is a hygroscopic insect-proofing composition, and more particularly a trioxane-containing composition which is useful in insect-proofing and damp proofing of clothing.

Hygroscopic insect-proofing composition

Disclosed is a composition comprising 1,3,5-trioxane, and more particularly a stability-improved trioxane composition.

Stability-improved trioxane composition

A process for producing a sulfonium compound of the formula (III) ##STR1## which process comprises reacting a p-dialkylsulfoniophenol of the formula (I) ##STR2## and a carbonyl halogenide compound of the formula (II) ##STR3## in the presence of a secondary amine having a structure in which two secondary alkyl groups are linked to the nitrogen atom, wherein R.sup.1 and R.sup.2 are the same or different and are independently an alkyl group having 1 to 4 carbon atoms, X.sup.1 is a hydrogen atom, a halogen atom or an alkyl group having 1 to 4 carbon atoms, Y.sup.- is a halogen anion, a perchlorate anion, an alkylsulfate anion, a hydrogensulfate anion or a p-toluenesulfonate anion, R is an alkyl group having 1 to 20 carbon atoms, a tert-butoxy group, a benzyloxy group, a p-methoxybenzyloxy group, a phenyl group or a 9-fluorenylmethoxy group, and X.sup.2 is a halogen atom, wherein the reacting is carried out in a solvent selected from the group consisting of polar aprotic solvents, ethers and halogenated hydrocarbons, at a temperature of -80.degree. C. to 30.degree. C. and for a reaction time of 0.5 hour to 10 hours.

In a process for producing a stabilized oxymethylene copolymer by heat-melting, at a temperature ranging between the melting point of the copolymer and a temperature 100.degree. C. higher than the melting point in a degassing apparatus in the presence of a heat stabilizer, a crude oxymethylene copolymer of trioxane with a cyclic acetal or cyclic ether, to decompose and eliminate the instable portions of the copolymer, the improvement which comprises using as the degassing apparatus in heat stabilizing the crude oxymethylene copolymer a combination of (A) an extruder and (B) a surface renewing-type mixer, and carrying out the operation by first feeding a crude oxymethylene copolymer to said extruder (A) to heat-melt and decompose 30-90% by weight of the instable portions of the crude copolymer, removing the decomposed gas via a vent provided in said extruder, and thereafter introducing the molten resin continuously to said surface renewing-type mixer (B) where substantially all of the remaining instable portions of the oxymethylene copolymer are heat-decomposed until the content of the instable portions falls below about 2 wt. %, thereby heat stabilizing the copolymer; said extruder (A) having a single or a plurality of shafts, said surface renewing-type mixer functioning to mix and knead the resin thereby constantly renewing the surface of the resin to volatize the volatiles contained therein.

Process for heat stabilizing oxymethylene copolymers

A process for producing a polyacetal homopolymer or copolymer which comprises continuously feeding a liquid starting mixture containing molten trioxane and a catalyst and optionally a comonomer through a feed opening of a reactor, said reactor being a continuously stirring-type mixer having two stirring shafts having a plurality of plate-like paddles fixed thereto the cross-section of each of said paddles taken perpendicularly of the axial direction of the stirring shaft having a shape of a convex lens, an ellipse or a quasipolygon inscribing a phantom circle at each vertex, one of said paddles facing another paddle fixed to the other stirring shaft and said one paddle being positioned such that it rotates while the edges thereof keep a slight clearance from the inner surface of the barrel and the other paddle; polymerizing the starting mixture while moving it toward the discharge opening by the rotation of the paddles, the improvement wherein the profiles of the paddles are changed, or the arrangement of the paddles is changed continuously or stepwise, so that the transportability of the reaction mixture becomes progressively smaller from the feed opening toward the discharge opening of the reactor.

Process for continuously polymerizing trioxane

In a process for producing an oxymethylene homopolymer or copolymer having improved stability which comprises polymerizing trioxane or a mixture of trioxane and a cyclic ether and/or a cyclic acetal in bulk in the presence of a catalyst which is at least one compound selected from the group consisting of boron trifluoride, boron trifluoride hydrate and coordination compounds of boron trifluoride with organic compounds containing an oxygen or sulfur atom, the improvement which comprises performing the bulk polymerization without destroying the bulk polymerization system, or which comprises adding a tertiary phosphine compound to the polymerization system to deactivate the catalyst, before the polymerization system formed by the bulk polymerization is destroyed.

Process for continuous production of oxymethylene polymer or copolymer

In a process for producing a stabilized oxymethylene copolymer which comprises heat-melting an oxymethylene copolymer having unstable, unblocked terminals obtained by the copolymerization of trioxane with a cyclic acetal and/or a cyclic ether to heat decompose it in the presence of available heat stabilizers; the improvement which comprises heating said oxymethylene copolymer having unblocked terminals in a mixer at a temperature between the melting point of said oxymethylene copolymer and a point 100.degree. C. higher than said melting point under a pressure of 0.1 mmHg to a atmospheric pressure for a mean residence time of 5 to 60 minutes, said mixer comprising a casing, a jacket for heating medium fitted over its external wall, and at least two stirring shafts equipped with a plurality of scraping blades disposed in said casing, said stirring shafts being capable of rotating in the same or different directions, and in the meantime, rotating said stirring shafts of said mixer to heat decompose said oxymethylene copolymer while renewing the surface of the molten oxymethylene copolymer.

Process for stabilizing oxymethylene copolymers

In a method for mixing a trioxane, a polymerization catalyst and a comonomer for producing of oxymethylene copolymers by continuously copolymerizing trioxane with a cyclic ether or a cyclic acetal as a comonomer, the improved method comprises following steps:

Method for mixing raw materials for producing oxymethylene copolymers

A process for polymerizing trioxane made from an aqueous solution of methanol-containing formaldehyde by a conventional method or copolymerizing the trioxane with another monomer, characterized by

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Tokyo, Japan

Mutsuhiko Takeda