Patents by Inventor Yutaka Nakahara
Yutaka Nakahara 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: 4362830Abstract: Hindered bis-phenol phenyl phosphites are provided having the structure: ##STR1## wherein: R is selected from the group consisting of alkyl having from one up to about eighteen carbon atoms; cycloalkyl having from three up to about twelve carbon atoms; alkaryl and aryl having from six to about eighteen carbon atoms; preferably, a bulky group such as iso, secondary or tertiary alkyl having from three to about ten carbon atoms; or cycloalkyl having six to twelve carbon atoms;R.sub.1 and R.sub.2 are each selected from the group consisting of hydrogen; alkyl having from one to about eighteen carbon atoms; cycloalkyl having from three up to about twelve carbon atoms; alkaryl and aryl having from six to about eighteen carbon atoms; and are preferably in a position ortho to a phenolic hydroxyl or phenoxy group, if available;R.sub.3 is alkylene having from one to about six carbon atoms;R.sub.Type: GrantFiled: December 29, 1980Date of Patent: December 7, 1982Assignee: Adeka Argus Chemical Co., Ltd.Inventors: Motonobu Minagawa, Yutaka Nakahara
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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: 4348308Abstract: An additive composition for improving the color stability of a vinyl chloride polymer stabilized with environmentally acceptable stabilizers comprises dehydroacetic acid or its Na, K., Li, Mg, Zn, Ba, Ca, Sn, or Sr salt and an organic phosphite having the formula ##STR1## wherein R.sub.1 is a t-butyl or t-amyl group, R.sub.2 is a hydrogen atom or an alkyl group having one to five carbon atoms, R.sub.3 is a hydrogen atom or a methyl group, and each of R.sub.4 and R.sub.5 independently is a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an ether-substituted group having 3 to about 50 carbon atoms and 1 to about 40 ether oxygen atoms.Type: GrantFiled: January 19, 1981Date of Patent: September 7, 1982Assignee: Adeka Argus Chemical Co., Ltd.Inventors: Motonobu Minagawa, Yutaka Nakahara, Kazumi Kitsukawa
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Patent number: 4346025Abstract: A stabilizer composition is disclosed that enhances the resistance to deterioration upon heating of vinyl chloride polymers. The stabilizer composition comprises (A) a metal salt of a nitrogen-free monocarboxylic acid or a phenol and (B) a hydrogen phosphite ester of an ortho-phenylethylidene-substituted phenol.Vinyl chloride polymer compositions stabilized with the above disclosed stabilizer composition are also disclosed.Type: GrantFiled: February 7, 1980Date of Patent: August 24, 1982Assignee: Adeka Argus Chemical Co., Ltd.Inventors: William E. Leistner, Motonobu Minagawa, Yutaka Nakahara, Kazumi Kitsukawa
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Patent number: 4336183Abstract: 2,2,6,6-Tetramethyl-4-piperidyl carboxylic acid esters and amides of mono and poly alcohols, phenols and amines are provided, useful as stabilizers for organic polymeric materials, and having the general formula: ##STR1##Type: GrantFiled: August 14, 1980Date of Patent: June 22, 1982Assignee: Adeka Argus Chemical Co., Ltd.Inventors: Yutaka Nakahara, Toshihiro Shibata, Naohiro Kubota
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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: 4309335Abstract: Ortho-substituted phenyl acid phosphite stabilizers for polyphenylene oxide resin compositions have the formula ##STR1## in which R.sub.1 is a t-butyl, t-amyl, cyclohexyl or phenyl group; R.sub.2 is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a cyclohexyl group, or a phenyl group; R.sub.3 is a hydrogen atom or a methyl group; and R.sub.4 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an ether-alkyl group having 3 to about 70 carbon atoms and 1 to 30 ether groups, an aryl group having 6 to 18 carbon atoms, a cycloalkyl group having 5 to 14 carbon atoms, an aralkyl, alkaryl, or alkoxyaryl group having 7 to 19 carbon atoms, an ethoxylated aryl or alkaryl group having 8 to 78 carbon atoms and 1 to 30 ether groups, or a cycloalkylaryl group having 11 to 19 carbon atoms.Type: GrantFiled: September 17, 1979Date of Patent: January 5, 1982Inventors: Mitsuo Akutsu, Yutaka Nakahara, Kazumi Kitsukawa
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Patent number: 4298520Abstract: This invention relates to a new class of phenolic compounds containing a phosphorus acid ester group which are stabilizers for synthetic resins and to synthetic resin stabilizer compositions comprising these phenolic compounds as well as to synthetic resins stabilized with such phenolic compounds and with stabilizer compositions comprising these phenolic compounds along with known polymer stabilizers.Type: GrantFiled: October 11, 1979Date of Patent: November 3, 1981Assignee: Argus Chemical Corp.Inventors: Motonobu Minagawa, Yutaka Nakahara, Masayuki Takahashi
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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: 4282141Abstract: An additive composition for improving the color stability of a vinyl chloride polymer stabilized with environmentally acceptable stabilizers comprises a 1,3-diketone or 1,3-diketone Na, K., Li, Mg, Zn, Ba, Ca, Sn, or Sr salt and an organic phosphite having the formula ##STR1## wherein R.sub.1 is a phenyl, cycloalkyl, t-butyl, or t-amyl group, R.sub.2 and R.sub.3 are each a hydrogen atom or phenyl, cycloalkyl, or an alkyl group having one to five carbon atoms, R.sub.4 is a hydrogen atom or a methyl group, and each of R.sub.5 and R.sub.6 independently is a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an ether-substituted group having 3 to 80 carbon atoms and 1 to about 40 ether oxygen atoms.Type: GrantFiled: July 13, 1979Date of Patent: August 4, 1981Assignee: Argus Chemical CorporationInventors: Motonobu Minagawa, Yutaka Nakahara, Kazumi Kitsukawa
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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: 4255301Abstract: Stabilizer compositions comprising a polymer stabilizer and a carbonate ester of cyclic dihydroxy compounds protect synthetic resins against the harmful effects of light having a wavelength less than 400 nanometers. The carbonate ester can be represented by the formula ##STR1## in which a is a number from 1 to 50, A is hydrogen or ##STR2## B is R' or --G--OH, R and R' are independently alkyl, alkoxyalkyl, cycloalkyl, aryl, aryloxyalkyl, aralkyl, or alkaryl groups, and G in at least one occurrence is a residue of a cycloaliphatic or non-aromatic oxygen heterocyclic dihydroxy compound having 3 to 20 carbon atoms and 1 or 2 rings of 3 to 12 members, of which up to 4 can be oxygen. Additional occurrences of G can be aliphatic glycol or bisphenol residues if desired.Type: GrantFiled: May 10, 1978Date of Patent: March 10, 1981Assignee: Argus Chemical CorporationInventors: Motonobu Minagawa, Yutaka Nakahara, Naohiro Kubota
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Patent number: 4252958Abstract: There is disclosed a process for preparing 2,2,6,6-Tetramethyl-4-oxopiperidine (triacetoneamine), in which a hydrazine hydrohalide salt catalyzes the reaction of an acetone compound, for example acetone or diacetone alcohol, with an ammonia donor compound, for example ammonia or 2,2,4,4,6-pentamethyl-1,2,5,6-tetrahydropyrimidine (acetonine).Type: GrantFiled: December 21, 1978Date of Patent: February 24, 1981Assignee: Argus Chemical CorporationInventors: Bunji Hirai, Naohiro Kubota, Yutaka Nakahara
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Patent number: 4250312Abstract: A 2,2,6,6-tetramethyl-4-piperidone spiroketal carbinol compound of Formula I ##STR1## in which R.sub.1 represents an alkyl group having from one to six carbon atoms, is prepared by heating a trimethylolalkane compound having the formula R.sub.1 --C(CH.sub.2 OH).sub.3 with a 2,2,6,6-tetramethyl-4-piperidone ketal compound of Formula II ##STR2## in which R.sub.2 represents an alkyl group having from one to twelve carbon atoms or an ether-interrupted alkyl group having from three to twelve carbon atoms and from one to two ether oxygen atoms, removing alcohol R.sub.2 OH, and recovering 2,2,6,6-tetramethyl-4-piperidone spiroketal carbinol compound of Formula I.Type: GrantFiled: December 28, 1979Date of Patent: February 10, 1981Assignee: Argus Chemical Corp.Inventors: Yutaka Nakahara, Naohiro Kubota, Toshihiro Shibata
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Patent number: 4250313Abstract: 2,2,6,6-Tetramethyl-4-piperidone spiroketal carbinol compound of Formula I ##STR1## in which R.sub.1 represents hydrogen, alkyl of one to ten carbon atoms, or aralkyl of seven to ten carbon atoms, and R.sub.2 represents alkyl of one of one to six carbon atoms, is prepared by heating a mixture of a 2,2,6,6-tetramethyl-4-piperidone compound of Formula II ##STR2## or an acid addition salt thereof, and a 1,3 dioxane compound having the formula III ##STR3## in which R.sub.3 and R.sub.4 represent R.sub.1 or aryl of six to ten carbon atoms or taken together represent alkylene of four to eight carbon atoms, removing R.sub.3 R.sub.4 CO compound and recovering 2,2,6,6-tetramethyl-4-piperidonespiroketal compound.Type: GrantFiled: February 1, 1980Date of Patent: February 10, 1981Assignee: Argus Chemical Corp.Inventors: Yutaka Nakahara, Naohiro Kubota, Toshihiro Shibata
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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: 4225474Abstract: 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 organophosphonic acid having linked to phosphorus as alkyl, aryl, aralkyl or alkaryl group optionally substituted with a phenolic hydroxyl group. The new coesters have molecular weights up to a maximum of about 10,000, preferably from 1000 to 9000, 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 2, 1978Date of Patent: September 30, 1980Assignee: Argus Chemical Corp.Inventors: Motonobu Minagawa, Yutaka Nakahara, Masayuki Takahashi
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Patent number: 4222931Abstract: Stabilizers for organic polymeric materials are provided, comprising a phosphonic acid ester, a phenolic antioxidant and a 2,2,6,6-tetramethyl-4-piperidyl ether alcohol or ether having the general formula: ##STR1## wherein R.sub.2 is lower alkyl or hydroxyalkyl having from one to six carbon atoms;R.sub.3 is a hydrogen atom, provided R.sub.2 is hydroxyalkyl; ##STR2## R.sub.2 and R.sub.3 may be taken together to form ##STR3## Y is selected from the group consisting of hydrogen and O.Type: GrantFiled: December 8, 1977Date of Patent: September 16, 1980Assignee: Argus Chemical CorporationInventors: Motonobu Minagawa, Yutaka Nakahara, Naohiro Kubota, Toshihiro Shibata