Patents Assigned to Toagosei Chemical Industry Co., Ltd.
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Patent number: 4425473Abstract: Certain new derivatives of 2,6,7-trioxabicyclo[2,2,2]octane are found to undergo cationic ring-opening polymerization with positive expansion in volume or with no substantial change in volume, in contrast with known polymerizable compounds such as epoxides which present considerable shrinkage in volume on polymerization. These new bicyclic orthoester compounds can be prepared in a facile way known per se.Type: GrantFiled: February 2, 1981Date of Patent: January 10, 1984Assignee: Toagosei Chemical Industry Co., Ltd.Inventors: Kiyokazu Mizutani, Takahisa Ogasawara
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Patent number: 4393183Abstract: An adhesive composition comprising 2-cyanoacrylate and at least one compound selected from the group consisting of R.sub.1 --CH.sub.2 OH, ##STR1## R.sub.1 --CHO, R.sub.1 --CHO hydrate, ##STR2## pentafluorophenol, hexachloroacetone, hexachloroacetone hydrate, chloral and chloral hydrate as cationic-polymerization inhibitor. In the above formulas, R.sub.1 is a fluorinated alkyl or aryl group having up to 12 carbon atoms, and R.sub.2 and R.sub.3 are fluorinated or non-fluorinated alkyl or aryl groups having up to 12 carbon atoms. The above adhesive composition has an excellent storage stability and an improved bonding strength.Type: GrantFiled: December 11, 1981Date of Patent: July 12, 1983Assignee: Toagosei Chemical Industry Co., Ltd.Inventors: Kaoru Kimura, Kyoji Sugiura
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Patent number: 4370387Abstract: A precoated steel sheet and a process for production thereof is provided which comprises coating a resin composition comprising mainly an acryloxyloxy- or methacryloyloxy-terminated polyester on the surface of a steel sheet, said acryloyloxy- or methacryloyloxy-terminated polyester being prepared by reacting a hydroxy-terminated polyester comprising (a) a dicarboxylic acid unit containing about 10 to about 80 mol % of a terephthalic acid unit and (b) dihydric alcohol unit containing about 30 mol % or more of a dihydric alcohol unit containing 3 or more carbon atoms, and having a number average molecular weight of about 400 to about 5,000, with acrylic acid or methacrylic acid, and curing the thus-coated resin composition by irradiating the sheet with an electron beam.Type: GrantFiled: March 19, 1981Date of Patent: January 25, 1983Assignees: Toagosei Chemical Industry Co., Ltd., Nippon Steel CorporationInventors: Nagaharu Ueno, Joji Oka, Hidejiro Asano, Takahisa Ogasawara, Kiyokazu Mizutani, Yoshiitsu Tominaga
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Patent number: 4364876Abstract: 2-Cyanoacrylate represented by the formula: ##STR1## wherein R.sup.1 is a 1,2-alkylene group having 2-4 carbon atoms; R.sup.2 is an alkylene group having 2-4 carbon atoms and R.sup.3 is an alkyl group having 1-6 carbon atoms, said 2-cyanoarylates can be anion-polymerized with a slight quantity of water similarly to hitherto known 2-cyanoacrylates, and the resulting cured product is richer in flexibility than the hitherto known ones. Therefore, it is not only useful as an instant-setting adhesive for metals, plastics, wood and ceramics but also is particularly useful as an adhesive for flexible materials such as rubber, leather, cloth and fiber. Further, said 2-cyanoacrylates are also useful as a coating material and a molding material.Type: GrantFiled: March 16, 1981Date of Patent: December 21, 1982Assignee: Toagosei Chemical Industry Co., Ltd.Inventors: Kaoru Kimura, Kazuyuki Sakabe
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Patent number: 4332731Abstract: Novel 2-methylene-1,4,6-trioxaspiro[4,6]undecane has both cationic polymerizability and radical ring-opening polymerizability, and it can be produced by reacting a 2-halomethyl-1,4,6-trioxaspiro[4,6]undecane with an alkali to effect dehydrohalogenation.Type: GrantFiled: September 17, 1980Date of Patent: June 1, 1982Assignee: Toagosei Chemical Industry Co., Ltd.Inventors: Takeshi Endo, Takahisa Ogasawara, Kiyokazu Mizutani
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Patent number: 4330643Abstract: A process for production of an acryloyloxy- or methacryloyloxy-terminated polyester is described, which comprises reacting a specific hydroxy-terminated polyester with acrylic acid or methacrylic acid, wherein the hydroxy-terminated polyester comprises (a) a dicarboxylic acid unit comprising about 10 to about 80 mol % of a terephthalic acid unit and about 90 to about 20 mol % of another dicarboxylic acid unit and (b) a dihydric alcohol unit containing about 30 mol % or more of a dihydric alcohol unit containing 3 or more carbon atoms and having a number average molecular weight of about 400 to about 5,000.Type: GrantFiled: February 23, 1981Date of Patent: May 18, 1982Assignee: Toagosei Chemical Industry Co., Ltd.Inventors: Takahisa Ogasawara, Kiyokazu Mizutani
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Patent number: 4321180Abstract: An adhesive composition consisting essentially of (A) an alkyloxyalkyl 2-cyanoacrylate represented by the formula, ##STR1## wherein R is an alkylene group having 2 to 4 carbon atoms and R' is an alkyl group having 2 to 6 carbon atoms, or tetrahydrofurfuryl 2-cyanoacrylate, (B) 300 to 2,000 ppm. of water, (C) a radical-polymerization inhibitor, and (D) an anionic-polymerization inhibitor. This adhesive composition is useful as an instant-setting adhesive for metals, plastics, rubbers, glass, wood and the like, is excellent in instant-setting properties, bond strength and storage stability, and neither emits an irritating odor nor causes whitening of the adherend surface.Type: GrantFiled: November 21, 1980Date of Patent: March 23, 1982Assignee: Toagosei Chemical Industry Co., Ltd.Inventors: Kaora Kimura, Kyoji Sugiura
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Patent number: 4196271Abstract: An adhesive composition comprising a 2-cyanoacrylate and at least one member selected from the group consisting of substituted or unsubstituted aliphatic carboxylic acids having three or more carboxyl groups, anhydrides thereof, partial esters thereof, aromatic polycarboxylic acids having three or more carboxyl groups and anhydrides thereof. This composition has a high impact strength, is suitable for bonding metallic substrates to one another and is also excellent in resistance to heat, weather, and water.Type: GrantFiled: December 22, 1976Date of Patent: April 1, 1980Assignee: Toagosei Chemical Industry Co., Ltd.Inventors: Akira Yamada, Kaoru Kimura
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Patent number: 4171416Abstract: A fast-setting .alpha.-cyanoacrylate-type adhesive composition having good storage stability comprising an .alpha.-cyanoacrylate and about 0.1 ppm or more of at least one macrocyclic polyether compound or an analogue thereof, such as 18-crown-6 or 15-crown-5.Type: GrantFiled: April 19, 1978Date of Patent: October 16, 1979Assignee: Toagosei Chemical Industry Co., Ltd.Inventors: Akira Motegi, Eiji Isowa, Kaoru Kimura
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Patent number: 4170585Abstract: An adhesive composition comprising an .alpha.-cyanoacrylate and about 0.0001% by weight to about 20% by weight, based on the weight of the adhesive composition, of at least one compound selected from the group consisting of(1) polyethylene glycols having a degree of polymerization of at least 3, and(2) non-ionic surface active agents having a poly(ethyleneoxy) moiety therein with the poly(ethyleneoxy) moiety having a degree of polymerization of at least 3.Type: GrantFiled: August 7, 1978Date of Patent: October 9, 1979Assignee: Toagosei Chemical Industry Co., Ltd.Inventors: Akira Motegi, Kaoru Kimura
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Patent number: 4169006Abstract: A method for bonding steel plates with a polyamide adhesive, comprising applying a composition comprising (1) a polyester resin comprising the reaction product of (a) a polycarboxylic acid component comprising at least one of a polycarboxylic acid, an anhydride thereof, an ester thereof or a mixture thereof with (b) a polyhydric alcohol component comprising at least one polyhydric alcohol or a mixture thereof, with at least some of one of the polycarboxylic acid component and the polyhydric alcohol component being trivalent or higher, and (2) a bisphenol A-type epoxy resin, on a steel plate; baking the coating by heating; juxtaposing the coated steel plates to be bonded with a polyamide adhesive therebetween; and bonding the steel plates with the polyamide adhesive, a primer composition for use therein and a polyester resin for use in the primer composition.Type: GrantFiled: June 22, 1977Date of Patent: September 25, 1979Assignee: Toagosei Chemical Industry Co., Ltd.Inventors: Takashi Matsubara, Yoshiaki Fujimoto, Yushi Ishibashi
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Patent number: 4147682Abstract: An additive composition for use in papermaking comprises a water-soluble polymer having in its molecule --COOH groups and/or --SO.sub.3 H groups, polyaluminum chloride and an aqueous solvent. Because of formation of a kind of crosslinking structure between the water-soluble polymer molecules through the polyaluminum chloride, the above composition exerts an effect of enhancing the paper strength when used alone and an effect of enhancing both the sizing effect and the paper strength when used together with a sizing agent. The composition further increases the paper strength when used in combination with a conventional paper-strength improver.Type: GrantFiled: December 7, 1977Date of Patent: April 3, 1979Assignees: Toagosei Chemical Industry Co., Ltd., Osakagodo Company Ltd.Inventors: Akira Yada, Isamu Iijima, Jo Itakura, Saburo Fujikura
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Patent number: 4146152Abstract: Disclosed herein is an opener for an adhesive container with a nozzle, which comprises a sharp member capable of making a hole in the closed end portion of the nozzle provided on the adhesive container body, the sharp member having a tapered sharp section which is used to make the hole in the closed end portion of the nozzle.Type: GrantFiled: August 29, 1977Date of Patent: March 27, 1979Assignee: Toagosei Chemical Industry Co. Ltd.Inventors: Shinichi Ogawa, Youichi Hirono
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Patent number: 4101493Abstract: An emulsion of a crosslinking type comprises an oligoester-(meth)acrylate having at least two (meth)acryloyl groups in a molecule, a molecular weight of not more than 1000 per one (meth)acryloyl group, and a boiling point at a normal pressure of at least 200.degree. C and a polymer emulsion of an oil-in-water type.Type: GrantFiled: July 13, 1976Date of Patent: July 18, 1978Assignee: Toagosei Chemical Industry Co., Ltd.Inventors: Teruo Nakagawa, Takahisa Ogasawara, Hidemaro Tatemichi
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Patent number: 4035436Abstract: A nylon-base adhesive composition for metals is composed of 100 parts by weight of a mixture of nylon 11 and nylon 12 and about 2-40 parts by weight of nylon 6-12. The adhesive composition has excellent heat resistance and water resistance and is particularly useful for making cans. The properties of the adhesive composition can be further improved by adding thereto polyethylene, an ionomer, or a mixture thereof.A process for bonding steel sheets using the adhesive is also disclosed.Type: GrantFiled: November 12, 1975Date of Patent: July 12, 1977Assignee: Toagosei Chemical Industry Co., Ltd.Inventors: Takashi Matsubara, Yoshihito Uramoto, Daizo Matsuoka
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Patent number: 4001097Abstract: Process for curing an oligoacrylate containing 3-6 acryloyl groups and at least one cyclohexene nucleus in the molecule and having an acryloyl group equivalent of not more than 1000, together with or without at least one other compound copolymerizable therewith, under the action of ionizing radiant rays in a molecular oxygen-containing gas to obtain a cured product from said oligoacrylate.Type: GrantFiled: August 29, 1974Date of Patent: January 4, 1977Assignee: Toagosei Chemical Industry Co., Ltd.Inventors: Takahisa Ogasawara, Yoshimichi Senzaki, Hiroyuki Kato, Hidemaro Tatemichi
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Patent number: 3993841Abstract: A coated steel plate suitable for bonding with a polyamide adhesive comprising a steel plate having coated thereon (a) a composition comprising a thermosetting phenol resin and a bisphenol A type epoxy resin, the thermosetting phenol resin comprising the condensation product obtained on reacting under refluxing a phenol and formaldehyde in less than one mol per equivalent of the phenolic hydroxyl group in the presence of an alkali catalyst; (b) a composition comprising a thermosetting phenol resin and a bisphenol A type epoxy resin, the thermosetting phenol resin comprising the condensation product obtained by washing with water the condensation product obtained by reacting under refluxing a phenol and formaldehyde in less than one mol per equivalent of the phenolic hydroxyl group in the presence of an alkali catalyst and then heating the condensation product to temperatures above about 60.degree.Type: GrantFiled: February 10, 1975Date of Patent: November 23, 1976Assignee: Toagosei Chemical Industry Co., Ltd.Inventors: Takashi Matsubara, Yuko Takeuchi, Toshiro Hirose
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Patent number: 3936342Abstract: A process for bonding steel sheets, e.g., into metallic cans, which comprises applying first a primer comprising 0.1 to 2.5 weight parts of a bisphenol type A epoxy resin having a mean molecular weight of more than about 800, preferably 2000 to 4000, and 1 weight part of thermosetting phenolic resin, which is obtained by heating an aqueous solution comprising phenol, orthocresol and formaldehyde in the presence of a catalyst and reacting them with each other under refluxing conditions, on the surface of the steel sheets, heating the resultant steel sheets, and then bonding the steel sheets with a polyamide, and a primer composition for use in the process.Type: GrantFiled: February 14, 1974Date of Patent: February 3, 1976Assignee: Toagosei Chemical Industry Co., Ltd.Inventors: Takashi Matsubara, Yuko Takeuchi, Toshiro Hirose
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Patent number: 3932144Abstract: A coated metallic sheet adapted for use in making a can for foodstuff or other container. This sheet can be made by coating, upon a material sheet, a composition of a resol-type thermosetting phenolformaldehyde resin and a bisphenol "A" type epoxy resin. In said phenol-formaldehyde resin, the ratio by weight of orthocresol to phenol is between 60:40 and 10:90. Said epoxy resin has a mean molecular weight of 800 or more and is used in an amount of 0.2 to 1.5 part by weight per 1 part by weight of said phenol-formaldehyde resin in said composition. This composition used for the sheet displays an excellent adhesiveness particularly with respective to the use of a polyamide type adhesive.Type: GrantFiled: December 4, 1974Date of Patent: January 13, 1976Assignees: Nippon Steel Corporation, Toagosei Chemical Industry Co., Ltd.Inventors: Takashi Matsubara, Yuko Takeuchi, Tadashi Tanaka, Tatsuro Obi, Akio Watanabe
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Patent number: D269531Type: GrantFiled: November 25, 1980Date of Patent: June 28, 1983Assignee: Toagosei Chemical Industry Co., Ltd.Inventor: Tsuneo Ando