Patents by Inventor Tohru Haruna
Tohru Haruna has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 4418196Abstract: A process is provided for preparing triacetone amine (2,2,6,6-tetramethyl-4-oxo piperidine) by reacting acetone and/or an acid condensate of acetone with ammonia in the presence of at least one catalyst selected from the group consisting of organotin halides, 1,3,5,2,4,6-triazatriphosphorin hexahalides and cyanuric halides.Type: GrantFiled: August 23, 1982Date of Patent: November 29, 1983Assignee: Adeka Argus Chemical Co., Ltd.Inventors: Yutaka Nakahara, Naohiro Kubota, Bunji Hirai, Tohru Haruna
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Patent number: 4349468Abstract: A new process for preparing a polyhydric alcohol 3-alkylthiopropionate polyolefin resin stabilizer is provided, comprising the steps of heating at 40.degree.-160.degree. C. an alpha-olefin having 6 to 28 carbon atoms with betamercaptopropionic acid or a lower alkyl betamercaptopropionate in the presence of an organic peroxide or azonitrile reaction initiator, esterifying the resulting 3-alkylthiopropionic acid or ester with pentaerythritol or tris(2-hydroxyethyl) cyanurate, and recovering the polyhydric alcohol 3-alkylthiopropionate polyolefin resin stabilizer from the mixture.Polyolefin resin compositions stabilized with the stabilizer prepared by the process of this invention, and stabilizer compositions comprising the stabilizer prepared by the process of this invention together with a phenol and/or an alkaline earth metal salt of a monocarboxylic acid are also provided.Type: GrantFiled: November 28, 1980Date of Patent: September 14, 1982Assignee: Adeka Argus Chemical Co., Ltd.Inventors: Yutaka Nakahara, Tohru Haruna
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Patent number: 4321191Abstract: Stabilizer compositions are provided to increase the resistance of a synthetic resin to deterioration upon heating, comprising in combination (A) a thiodipropionic acid ester of a dihydric alcohol having 2 to 20 carbon atoms and an alcohol or carboxylic acid chain terminator having 1 to 21 carbon atoms, and (B) a 700 to about 10,000 molecular weight ester of a polyhydric phenol with carbonic acid or with carbonic acid and another acid which can be an aliphatic dicarboxylic acid, phosphorous acid, phosphoric acid, boric acid, or an organophosphonic acid.Synthetic resins that can be stabilized with composition of the invention include polymers of alpha-olefins having 2 to 6 carbon atoms, vinyl chloride polymers, acrylonitrile-butadiene-styrene polymers, and terephthalic acid ester polymers.Type: GrantFiled: October 11, 1979Date of Patent: March 23, 1982Assignee: Argus Chemical Corp.Inventors: Motonobu Minagawa, Yutaka Nakahara, Tohru Haruna
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Patent number: 4293472Abstract: New ortho-alkylhydroxybenzyl substituted propanediol compounds of carboxylic acids, aldehydes, ketones, phosphites, phosphates, and phosphonates are disclosed. The propanediol compounds have in the molecule from one to four preferably from one to three ortho-alkylhydroxybenzylpropanediol units, each of which carries one to two ortho-alkylhydroxybenzyl groups, and are highly effective stabilizers for a variety of synthetic resins.Stabilizer compositions comprising a orthoalkylhydroxybenzylpropanediol compound and a known polymer stabilizer, as well as synthetic resins stabilized with such stabilizer compositions, are also disclosed.Type: GrantFiled: April 24, 1979Date of Patent: October 6, 1981Inventors: Motonobu Minagawa, Yutaka Nakahara, Tohru Haruna
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Patent number: 4257927Abstract: New polyhydric phenol coesters are disclosed of polyhydric phenols, having 2 to 3 phenolic hydroxyl groups and 1 to 3 benzenoid rings, with carbonic acid and an inorganic acid which can be phosphorous acid, phosphoric acid, and boric acid. The new coesters have molecular weights from 700 to about 10,000, preferably from 1200 to 7000, and are highly effective stabilizers for a variety of synthetic resins.Stabilizer compositions comprising a polyhydric phenol coester and a known polymer stabilizer, as well as synthetic resins stabilized with such stabilizer compositions, are also disclosed.Type: GrantFiled: October 5, 1978Date of Patent: March 24, 1981Assignee: Argus Chemical Corp.Inventors: William E. Leistner, Motonobu Minagawa, Yutaka Nakahara, Tohru Haruna
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Patent number: 4239803Abstract: A composition for enhancing and maintaining mechanical properties such as tensile strength of an ethylene polymer on heating at elevated temperature comprises (A) an initiator of cross-linking having a half-life measured at 110.degree. C. of 0.1 to 50 hours and (B) an alkylthioalkylenecarboxylic acid ester of a polycarbocyclic polyhydric phenol.Type: GrantFiled: June 14, 1977Date of Patent: December 16, 1980Assignee: Argus Chemical CorporationInventors: Toshio Ohzeki, Mitsuo Akutsu, Yutaka Nakahara, Tohru Haruna, Motonobu Minagawa, Masahiro Nonoyama
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Patent number: 4233414Abstract: New polyhydric phenol coesters are disclosed of polyhydric phenols, having 2 to 3 phenolic hydroxyl groups and 1 to 3 benzenoid rings, with carbonic acid and an aliphatic dicarboxylic acid having 4 to 10 carbon atoms and optionally a thioether sulfur atom in the aliphatic chain of the dicarboxylic acid. The new coesters have molecular weights from 700 to about 10,000, preferably from 1200 to 7000, and are highly effective stabilizers for a variety of synthetic resins.Stabilizer compositions comprising a polyhydric phenol coester and a known polymer stabilizer, as well as synthetic resins stabilized with such stabilizer compositions, are also disclosed.Type: GrantFiled: May 29, 1979Date of Patent: November 11, 1980Assignee: Argus Chemical CorporationInventors: William E. Leistner, Motonobu Minagawa, Yutaka Nakahara, Tohru Haruna
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Patent number: 4226991Abstract: A new process for preparing a polyhydric alcohol 3-alkyl-thiopropionate polyolefin resin stabilizer is provided, in which there is heated a reaction mixture containing a polyhydric alcohol, an alpha-olefin having 6 to 40 carbon atoms, and betamercaptopropionic acid or a lower alkyl betamercaptopropionate in the presence of an organic peroxide or azonitrile reaction initiator, and the polyhydric alcohol 3-alkylthiopropionate polyolefin resin stabilizer is recovered from the mixture.Polyolefin resin compositions stabilized with the stabilizer prepared by the process of this invention, and stabilizer compositions comprising the stabilizer prepared by the process of this invention together with a phenol and/or an alkaline earth metal salt of a monocarboxylic acid are also provided.Type: GrantFiled: October 13, 1978Date of Patent: October 7, 1980Assignee: Argus Chemical Corp.Inventors: Yutaka Nakahara, Tohru Haruna, Kenji Tazima
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Patent number: 4219463Abstract: Stabilizers for organic polymeric materials are provided, comprising a 2,2,6,6-tetramethyl-4-piperidyl carboxylic acid ester having the general formula: ##STR1## wherein: R.sub.1 is selected from the group consisting of ##STR2## Y is selected from the group consisting of hydrogen and O; R.sub.Type: GrantFiled: November 17, 1977Date of Patent: August 26, 1980Assignee: Argus Chemical CorporationInventors: Motonobu Minagawa, Naohiro Kubota, Tohru Haruna, Toshihiro Shibata
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Patent number: 4174297Abstract: New polyhydric phenol coesters are disclosed of polyhydric phenols, having 2 to 3 phenolic hydroxyl groups and 1 to 3 benzenoid rings, with carbonic acid and an aliphatic dicarboxylic acid having 4 to 10 carbon atoms and optionally a thioether sulfur atom in the aliphatic chain of the dicarboxylic acid. The new coesters have molecular weights from 700 to about 10,000, preferably from 1200 to 7000, and are highly effective stabilizers for a variety of synthetic resins.Stabilizer compositions comprising a polyhydric phenol coester and a known polymer stabilizer, as well as synthetic resins stabilized with such stabilizer compositions, are also disclosed.Type: GrantFiled: November 9, 1976Date of Patent: November 13, 1979Assignee: Argus Chemical CorporationInventors: William E. Leistner, Motonobu Minagawa, Yutaka Nakahara, Tohru Haruna
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Patent number: 4146517Abstract: New polyhydric phenol coesters are disclosed of polyhydric phenols, having 2 to 3 phenolic hydroxyl groups and 1 to 3 benzenoid rings, with carbonic acid and an inorganic acid which can be phosphorous acid, phosphoric acid, and boric acid. The new coesters have molecular weights from 700 to about 10,000, preferably from 1200 to 7000, and are highly effective stabilizers for a variety of synthetic resins.Stabilizer compositions comprising a polyhydric phenol coester and a known polymer stabilizer, as well as synthetic resins stabilized with such stabilizer compositions, are also disclosed.Type: GrantFiled: February 28, 1977Date of Patent: March 27, 1979Assignee: Argus Chemical CorporationInventors: William E. Leistner, Motonobu Minagawa, Yutaka Nakahara, Tohru Haruna
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Patent number: 4107136Abstract: Stabilizer compositions are provided whose ingredients interact synergistically to improve the resistance to deterioration on heating of a variety of synthetic resin compositions. The interacting ingredients are (a) an organic phosphite having linked to phosphorus through oxygen at least two alkyl groups having from 6 to 20 carbon atoms and at least one organic group selected from polycyclic polyhydric phenol groups and pentaerythrityl groups, and (b) at least one carbonate ester of an ortho-substituted polyhydric phenol having in the molecule one to three benzenoid rings, two to three phenolic hydroxyl groups, and in each benzenoid ring one to two alkyl, cycloalkyl, or aralkyl groups of which at least one is positioned ortho to a phenolic hydroxyl group.Synthetic resin compositions are provided that are stabilized with the stabilizer compositions disclosed, including olefin polymers, polyamides, acrylic polymers, and vinyl halide polymers.Type: GrantFiled: October 6, 1976Date of Patent: August 15, 1978Assignee: Argus Chemical CorporationInventors: Motonobu Minagawa, Yutaka Nakahara, Tohru Haruna
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Patent number: 4105629Abstract: Stabilizer compositions are provided whose ingredients interact synergistically to improve the resistance to deterioration on heating of synthetic resin compositions. The interacting ingredients are (a) a thioether carboxylic acid ester of a polyhydric alcohol having 5 to 15 carbon atoms and 3 to 8 primary hydroxyl groups with a 3-alkylthiopropionic acid having 4 to about 34 carbon atoms, and (b) at least one carbonate ester of an ortho-substituted polyhydric phenol having in the molecule one to three benzenoid rings, two to three phenolic hydroxyl groups, and in each benzenoid ring one to two alkyl, cycloalkyl, or aralkyl groups of which at least one is positioned ortho to a phenolic hydroxyl group.Synthetic resin compositions are provided that are stabilized with the stabilizer compositions disclosed, including olefin polymers, polyamides, acrylic polymers, and vinyl halide polymers.Type: GrantFiled: October 13, 1976Date of Patent: August 8, 1978Assignee: Argus Chemical CorporationInventors: Motonobu Minagawa, Yutaka Nakahara, Tohru Haruna
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Patent number: 4104217Abstract: This invention relates to a new class of polyhydric phenol carbonate esters and to synthetic resin stabilizer compositions comprising these esters as well as to synthetic resins stabilized with such esters and with stabilizer compositions comprising these esters along with known polymer stabilizers.Type: GrantFiled: January 24, 1977Date of Patent: August 1, 1978Assignee: Argus Chemical CorporationInventors: William E. Leistner, Motonobu Minagawa, Yutaka Nakahara, Tohru Haruna