Patents Assigned to Adeka Argus Chemical Co., Ltd.
  • Patent number: 4405737
    Abstract: N-2-Hydroxypropyl piperidines are provided, as well as a process for preparing these compounds, having the formula: ##STR1## wherein X is selected from the group consisting of , ##STR2## wherein R.sub.1 is selected from the group consisting of hydrogen; alkyl; alkenyl; cycloalkyl; alkaryl; hydroxyalkyl; oxyalkyl; acyl and aroyl having from one to about eighteen carbon atoms;R.sub.2 and R.sub.3 are each selected from the group consisting of alkyl, alkenyl, cycloalkyl, alkaryl, hydroxyalkyl, oxyalkyl and haloalkyl having from one to about eighteen carbon atoms;R.sub.4, R.sub.5 and R.sub.6 each are selected from the group consisting of hydrogen, alkyl, alkenyl, cycloalkyl, alkaryl, hydroxyalkyl, oxyalkyl and haloalkyl having from one to about eighteen carbon atoms; and --CH.sub.2 --O--R.sub.1 ;n is 1 or 2; andY, when n is 1, is hydroxy or ##STR3## and when n is 2, is oxyoxygen.
    Type: Grant
    Filed: February 5, 1982
    Date of Patent: September 20, 1983
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Bunji Hirai, Naohiro Kubota, Kazuo Sugibuchi
  • Patent number: 4404301
    Abstract: Polymeric light stabilizers are provided having at least one 2,2,6,6-tetraalkyl piperidyl group in the molecule and a molecular weight within the range from about 1000 to about 20,000, that are polymers of an unsaturated carboxylic acid ester selected from the group consisting of unsaturated cycloaliphatic mono-, di, and tri-carboxylic acid esters having from seven to about thirty carbon atoms; unsaturated branched-chain aliphatic di- and tri-carboxylic acid esters having from four to about thirty carbon atoms; sorbic acid ester, 3,8-nonadienyl acid ester, oleic acid ester, linolenic acid ester and ricinoleic acid ester; or copolymers of at least one thereof with another copolymerizable unsaturated monomer; and synthetic resin compositions having improved light stability comprising per 100 parts by weight of resin from 0.001 to 10 parts by weight of the polymeric light stabilizer.
    Type: Grant
    Filed: April 22, 1982
    Date of Patent: September 13, 1983
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Naohiro Kubota, Toshihiro Shibata, Ryozo Arata
  • Patent number: 4396735
    Abstract: Light stabilizers for synthetic resin compositions and synthetic resin compositions containing such stabilizers are provided, comprising(1) at least one hindered heterocyclic amine having the formula: ##STR1## wherein: X is a bivalent linking radical forming with the ring structure ##STR2## a nitrogen-containing heterocyclic ring having from five to seven ring atoms, preferably piperidine;R.sub.1 and R.sub.2 are each selected from the group consisting of lower alkyl, preferably methyl, and R.sub.1 and R.sub.2 taken together as pentylene (CH.sub.2).sub.5 ;R.sub.3 and R.sub.4 are each selected from the group consisting of lower alkyl, and R.sub.3 and R.sub.4 taken together as one of butylene--(CH.sub.2).sub.4, pentylene--(CH.sub.2).sub.5, and CH.sub.2 --C(CH.sub.3).sub.2 --NH--C(CH.sub.3).sub.2 --CH.sub.2 --;n is 1 or 2; andwhen n is 1, Y.sub.1 is selected from the group consisting of hydrogen, O.sup..cndot.
    Type: Grant
    Filed: October 3, 1980
    Date of Patent: August 2, 1983
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata
  • Patent number: 4378443
    Abstract: 2,2,6,6-Tetraalkyl-4-piperidyl-bis-spiro-ethers are provided, useful as stabilizers for lessening deterioration due to exposure to light of organic polymeric materials, and having the general formula: ##STR1##
    Type: Grant
    Filed: October 8, 1980
    Date of Patent: March 29, 1983
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata
  • Patent number: 4371646
    Abstract: 2,6-Di-tertiary butyl phenyl phosphites are provided having the structure ##STR1## as well as synthetic resin compositions having an enhanced resistance to deterioration by heat and/or light due to the presence of an organic phosphite of this class.
    Type: Grant
    Filed: December 29, 1980
    Date of Patent: February 1, 1983
    Assignee: Adeka Argus Chemical Co. Ltd.
    Inventors: Motonobu Minagawa, Yutaka Nakahara
  • Patent number: 4371647
    Abstract: 2,6-Di-tertiary butyl phenyl pentaerythritol spiro bisphosphites are provided having the structure: ##STR1## wherein: R is alkyl having from one to six carbon atoms;R.sub.1 is methyl or ethyl;R.sub.2 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; and alkaryl and aryl having from six to about thirty carbon atoms; such groups substituted with from one to about four oxy ether--O-- and/or carboxylic ester--COO--groups; the residue of a polyhydric alcohol having from two to about eighteen carbon atoms, and from two to about ten hydroxyl groups; and the residue of a polyphenol having from six to about eighteen carbon atoms and from two to about ten phenolic hydroxyl groups.
    Type: Grant
    Filed: January 7, 1981
    Date of Patent: February 1, 1983
    Assignee: Adeka Argus Chemical Co. Ltd.
    Inventors: Motonobu Minagawa, Yutaka Nakahara, Etsuo Tobita
  • Patent number: 4362831
    Abstract: Light and heat stabilizers for synthetic resin compositions and synthetic resin compositions containing such stabilizers are provided, comprising(1) at least one hindered and heterocyclic amine having the formula: ##STR1## wherein: X is a bivalent linking radical forming with the ring structure ##STR2## a nitrogen-containing heterocyclic ring having from five to seven ring atoms, preferably piperidine;R.sub.1 and R.sub.2 are each selected from the group consisting of lower alkyl, preferably methyl, and R.sub.1 and R.sub.2 taken together as pentylene (CH.sub.2).sub.5 ;R.sub.3 and R.sub.4 are each selected from the group consisting of lower alkyl, and R.sub.3 and R.sub.4 taken together as one of butylene--(CH.sub.2).sub.4, pentylene--(CH.sub.2).sub.5, and CH.sub.2 --C(CH.sub.3).sub.2 --NH--C(CH.sub.3).sub.2 --CH.sub.2 --;n is 1 or 2; andwhen n is 1, Y is selected from the group consisting of hydrogen, O.degree.
    Type: Grant
    Filed: December 7, 1979
    Date of Patent: December 7, 1982
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Toshio Ohzeki, Mitsuo Akutsu, Takanori Semba
  • Patent number: 4362830
    Abstract: 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: Grant
    Filed: December 29, 1980
    Date of Patent: December 7, 1982
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Motonobu Minagawa, Yutaka Nakahara
  • Patent number: 4351915
    Abstract: 2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers which are useful as stabilizers for organic polymeric materials, and have the general formula are disclosed: ##STR1## wherein: Y.sub.1 is ##STR2## A.sub.1, A.sub.2, A.sub.3, A.sub.4, A.sub.5, and A.sub.6 are groups which are defined in the specification, at least one pair of A.sub.1 and A.sub.2 ; A.sub.3 and A.sub.4 ; and A.sub.5 and A.sub.6 being taken together to form the group ##STR3## the groups R.sub.1, R.sub.2, R.sub.3 and Z as well as X, p, and m being as defined in the specification.
    Type: Grant
    Filed: May 26, 1981
    Date of Patent: September 28, 1982
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Naohiro Kubota, Toshihiro Shibata, Kazuo Sugibuchi, Motonubu Minagawa
  • Patent number: 4349468
    Abstract: 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: Grant
    Filed: November 28, 1980
    Date of Patent: September 14, 1982
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Yutaka Nakahara, Tohru Haruna
  • Patent number: 4348308
    Abstract: 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: Grant
    Filed: January 19, 1981
    Date of Patent: September 7, 1982
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Motonobu Minagawa, Yutaka Nakahara, Kazumi Kitsukawa
  • Patent number: 4346025
    Abstract: 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: Grant
    Filed: February 7, 1980
    Date of Patent: August 24, 1982
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: William E. Leistner, Motonobu Minagawa, Yutaka Nakahara, Kazumi Kitsukawa
  • Patent number: 4336183
    Abstract: 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: Grant
    Filed: August 14, 1980
    Date of Patent: June 22, 1982
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Yutaka Nakahara, Toshihiro Shibata, Naohiro Kubota
  • Patent number: RE31261
    Abstract: 2,2,6,6-Tetrasubstituted-4-piperidyl carboxy heterocyclic compounds are provided which are useful as stabilizers for organic polymeric materials.
    Type: Grant
    Filed: November 27, 1981
    Date of Patent: May 31, 1983
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata