Patents Assigned to Argus Chemical Corporation
  • Patent number: 4169089
    Abstract: Synthetic resins processed at temperatures in excess of 200.degree. C. are protected against deterioration on exposure to light of wave length shorter than 400 nanometers by compounding with a stabilizer composition comprising (A) 40 to 90 parts by weight of at least one 5,5'-methylenebis(2-hydroxy-4-alkoxybenzophenone) having 1 to 18 carbon atoms in the alkoxy group, (B) 5 to 30 parts by weight of at least one 3,5'-methylenedi(2-hydroxy-4-alkoxybenzophenone) having 1 to 18 carbon atoms in the alkoxy group, (C) 5 to 40 parts by weight of at least one 3,3'-methylenebis(2-hydroxy-4-alkoxybenzophenone) having 1 to 18 carbon atoms in the alkoxy group. Synthetic resins suitably stabilized with compositions of the invention include thermoplastic polyesters such as polyhydric phenol carbonate polyesters and alkanediol terephthalate polyesters, as well as high melting polyolefins such as poly-4-methylpentene and polypropylene.
    Type: Grant
    Filed: March 31, 1978
    Date of Patent: September 25, 1979
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Naohiro Kubota, Kazuo Sugibuchi
  • Patent number: 4161485
    Abstract: Novel cyclic silylperoxides in which a silicon atom directly bonded to at least two peroxy oxygen atoms in a ring of from 8 to 11 atoms are useful as agents for crosslinking high density polyethylene and/or as catalysts for curing unsaturated polyester resins.
    Type: Grant
    Filed: June 12, 1978
    Date of Patent: July 17, 1979
    Assignee: Argus Chemical Corporation
    Inventors: Reidar Halle, Lawrence A. Bock
  • Patent number: 4160762
    Abstract: Stabilizer compositions are provided to enhance the resistance to deterioration on heating of a halogen-containing resin, comprising (A) a sulfide compound of four-valent tin having linked to a tin atom at least one sulfide group, and through carbon 1 or 2 alkoxycarbonylalkylene groups having from 1 to 8 carbon atoms in the alkoxy group and from 2 to 3 atoms in the alkylene group; and (B) a tin mercaptoalkylenecarboxylic acid ester having linked to a tin atom through sulfur 2 or 3 mercaptoalkylenecarboxylic acid alkyl ester groups having 1 or 2 carbon atoms in the mercaptoalkylene group and 4 to 18 carbon atoms in the alkyl ester group, and through carbon 1 or 2 alkoxycarbonylalkylene groups having from 1 to 8 carbon atoms in the alkoxy group and 2 or 3 carbon atoms in the alkylene group. The stabilizer composition contains at lesast 5% by weight of the sulfide compound (A).Halogen-containing resin compositions stabilized with the above stabilizer composition are also provided.
    Type: Grant
    Filed: June 14, 1977
    Date of Patent: July 10, 1979
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Tetsuo Sekiguchi
  • Patent number: 4154768
    Abstract: Increase in yields of alkyl hydroperoxides from corresponding olefins by reacting the olefin with an inorganic peroxide in the presence of an acid catalyst, the acid concentration being adjusted to an optimum range which is generally about 15-30% by total weight of the reactive ingredients. Where the olefin contains over 7 carbon atoms, peroxide-compatible surfactants are included in the reaction mixture and the yield of hydroperoxide is further improved.
    Type: Grant
    Filed: August 27, 1973
    Date of Patent: May 15, 1979
    Assignee: Argus Chemical Corporation
    Inventor: Newton G. Leveskis
  • Patent number: 4151339
    Abstract: A process for polymerizing vinyl chloride and for copolymerizing vinyl chloride and up to 30 percent by weight of comonomers in aqueous suspension under heat and pressure in the presence of a mixture of an acyl sulfonyl peroxide and a perester of the formula ##STR1## wherein R.sub.3, R.sub.4, and R.sub.5 are the same or different alkyl groups of from 1 to about 10 carbon atoms provided not more than one of R.sub.3, R.sub.4, and R.sub.5 is methyl, and R is selected from 2,2-dimethyl propyl and straight chain alkyl of 1-5 carbon atoms.
    Type: Grant
    Filed: November 1, 1974
    Date of Patent: April 24, 1979
    Assignee: Argus Chemical Corporation
    Inventors: Ronald L. Friedman, Roger N. Lewis
  • Patent number: 4146518
    Abstract: A stabilized halogen-containing resin composition by incorporating therein (a) at least one kind of mono alkyltin compounds or dialkyltin compounds and (b) at least one kind of monoalkoxycarbonylalkyltin compound or bis(alkoxycarbonylalkyl)tin compounds.
    Type: Grant
    Filed: July 21, 1977
    Date of Patent: March 27, 1979
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Tetsuo Sekiguchi
  • Patent number: 4146583
    Abstract: Cyclic and acyclic phenylene substituted dialkyl peroxides most of which are in an acyclic polymeric form.
    Type: Grant
    Filed: July 27, 1977
    Date of Patent: March 27, 1979
    Assignee: Argus Chemical Corporation
    Inventors: Roger N. Lewis, Lawrence A. Bock
  • Patent number: 4146517
    Abstract: 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: Grant
    Filed: February 28, 1977
    Date of Patent: March 27, 1979
    Assignee: Argus Chemical Corporation
    Inventors: William E. Leistner, Motonobu Minagawa, Yutaka Nakahara, Tohru Haruna
  • Patent number: 4145333
    Abstract: Synthetic resins such as polyolefins, vinyl chloride polymers, ABS polymers, ethylene-vinyl acetate copolymers and polyesters are stabilized against deteriorating influences with new stabilizer compositions comprising certain hydroxyphenylalkylenephosphonic acid esters of polycarbocyclic polyhydroxy compounds having the general formula (1) ##STR1## (wherein, R.sub.1 denotes alkyl or cycloalkyl, R.sub.2 and R.sub.3 denote a hydrogen atom, alkyl or cycloalkyl. R.sub.4 denotes alkyl, cycloalkyl, arylalkyl, aryl, alkylaryl, alkylpolyoxyalkylene or a residue of polyhydricphenol. A is a residue of polynuclearpolyhydric phenol or hydrogenated derivative thereof of from 2 to 4 valent. n is 1 to 8. m is 1 to 5. L is 0, 1 or 2.
    Type: Grant
    Filed: July 20, 1977
    Date of Patent: March 20, 1979
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Yutaka Nakahara, Masayuki Takahashi
  • Patent number: 4136081
    Abstract: 2,2,6,6-TETRAMETHYL-4-PIPERIDYL CARBOXYLIC ACID ESTERS OF ALIPHATIC TETRACARBOXYLIC ACIDS ARE PROVIDED, USEFUL AS STABILIZERS FOR ORGANIC POLYMERIC MATERIALS, AND HAVING THE GENERAL FORMULA: ##STR1## wherein: R.sub.1 is selected from the group consisting of ##STR2## and when a is 2, 3, or 4, the R.sub.1 groups can be the same or different; R.sub.2 is selected from the group consisting of hydrogen; alkyl; alkenyl; cycloalkyl; alkcycloalkyl; cycloalkalkyl; aryl; aralkyl; and alkaryl; and when b is 2 or 3, the R.sub.2 groups can be the same or different;R.sub.3 is selected from the group consisting of hydrogen and O;R.sub.6 is lower alkyl;A is selected from the group consisting of 1, 2, 3 and 4;B is selected from the group consisting of 0, 1, 2 and 3;A + b is equal to 4; and Z is a tetravalent aliphatic or cycloaliphatic radical carrying four ##STR3## WHERE R is R.sub.1 or R.sub.2, and can include from one to three hydroxyl groups OH.
    Type: Grant
    Filed: October 28, 1976
    Date of Patent: January 23, 1979
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata
  • Patent number: 4134868
    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 non-nitrogenous monocarboxylic acid or hydrocarbon-substituted phenol and (B) an aromatic carboxylic acid ester of a polyhydric alcohol having at least two alcoholic hydroxyl groups in a polyhydric alcohol aromatic carboxylic acid ester group.Vinyl chloride polymer compositions stabilized with the above disclosed stabilizer composition are also disclosed.
    Type: Grant
    Filed: February 7, 1977
    Date of Patent: January 16, 1979
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Tetsuo Sekiguchi, Kouji Tsuruga
  • Patent number: 4129613
    Abstract: Acyl peroxycarbonic esters of the formula ##STR1## in which R is methyl or ethyl, R' is alkyl, and R and R' together have 17 or more carbon atoms. The compounds have unusual thermal stability, together with improved polymerization initiating efficiency. Particularly outstanding efficiency is found in connection with the curing of polyester resins.
    Type: Grant
    Filed: July 21, 1977
    Date of Patent: December 12, 1978
    Assignee: Argus Chemical Corporation
    Inventors: Roger N. Lewis, Ronald L. Pastorino, James F. Wilts
  • Patent number: 4128608
    Abstract: 2,2,6,6-TETRAMETHYL-4-PIPERIDYL SPIRO ALIPHATIC ETHERS ARE PROVIDED, USEFUL AS STABILIZERS FOR ORGANIC POLYMERIC MATERIALS, AND HAVING THE GENERAL FORMULA: ##STR1## wherein: R.sub.1 is selected from the group consisting of hydrogen, lower alkyl and lower hydroxyalkyl having one or two carbon atoms; ##STR2## R.sub.3 is selected from the group consisting of hydrogen and O; and n is 0 to 1.
    Type: Grant
    Filed: December 8, 1977
    Date of Patent: December 5, 1978
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata
  • Patent number: 4124564
    Abstract: Stabilizer compositions are provided whose ingredients interact synergistically to improve the resistance to deterioration on light exposure and heating of synthetic resin compositions. The interacting ingredients are (a) a carboxylic acid ester of a 2,2,6,6-tetramethylpiperidine-4-alcohol having 15 to 75 carbon atoms and 1 to 4 ester 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 thestabilizer compositions disclosed, including olefin polymers, polyamides, acrylic polymers, and vinyl halide polymers.
    Type: Grant
    Filed: February 18, 1977
    Date of Patent: November 7, 1978
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata
  • Patent number: 4118369
    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: July 28, 1976
    Date of Patent: October 3, 1978
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata
  • Patent number: 4116927
    Abstract: 2,2,6,6-TETRAMETHYL-4-PIPERIDYL CARBOXYLIC ACID ESTERS OF BUTANE OR BUTENE TRICARBOXYLIC ACIDS ARE PROVIDED, USEFUL AS STABILIZERS FOR ORGANIC POLYMERIC MATERIALS, AND HAVING THE GENERAL FORMULA: ##STR1## wherein: R.sub.1 is selected from the group consisting of ##STR2## the R.sub.1 groups can be the same or different; R.sub.2 is selected from the group consisting of CH.sub.3 and CH.sub.2 ; andR.sub.3 is lower alkyl.
    Type: Grant
    Filed: July 5, 1977
    Date of Patent: September 26, 1978
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata
  • Patent number: 4115476
    Abstract: 2,2,6,6-Tetramethyl-4-piperidyl carbonic acid esters of dihydric alcohols and phenols are provided, useful as stabilizers for organic polymeric materials, and having the general formula: ##STR1## wherein: R.sub.1 and R.sub.2 are selected from the group consisting of ##STR2## the R.sub.1 and R.sub.2 groups can be the same or different; R.sub.3 is selected from the group consisting of hydrogen and O;R.sub.6 is lower alkyl;n is selected from the group consisting of 1, 2, 3, 4 and 5;--O --Z--O--is a bivalent aliphatic, cycloaliphatic, aromatic, or mixed aliphatic-aromatic, aliphatic-cycloaliphatic or cycloaliphatic-aromatic radical carrying two hydroxyl groups OH esterified with carbonic acid groups of the piperidyl carbonic acid ester.
    Type: Grant
    Filed: May 5, 1977
    Date of Patent: September 19, 1978
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata
  • Patent number: 4113678
    Abstract: Processability, color, and mechanical properties upon heating of a rubber modified styrene polymer are improved by incorporating in the polymer a new sulfide compound of four-valent tin having linked to tin through carbon 1 or 2 alkoxycarbonylalkylene groups having 1 to 8 carbon atoms in the alkoxy group and 2 to 3 carbon atoms in the alkylene group.
    Type: Grant
    Filed: June 14, 1977
    Date of Patent: September 12, 1978
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Toshio Ohzeki, Tetsuo Sekiguchi
  • Patent number: 4110306
    Abstract: Stabilizers for organic polymeric materials are provided, comprising a triphosphite, an acid phosphite, and 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: Grant
    Filed: November 22, 1976
    Date of Patent: August 29, 1978
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata
  • Patent number: 4107419
    Abstract: Organic peroxide polymerization co-initiator compositions and their use in the initiation of the polymerization of certain monomers and comonomers such as vinyl chloride, ethylene and methyl methacrylate. The co-initiator composition contains an alpha halo substituted diacyl peroxide and a coperoxide selected from t-alkyl peresters of t-hydroperoxides, peroxydicarbonates, acyl peroxycarbonic esters, and aliphatic diacyl peroxides. Typical is acetyl 2-chlorooctanoyl peroxide with t-butyl peroxy neodecanoate.
    Type: Grant
    Filed: March 4, 1977
    Date of Patent: August 15, 1978
    Assignee: Argus Chemical Corporation
    Inventors: Ronald L. Friedman, deceased, Roger N. Lewis