Patents Assigned to Argus Chemical Corporation
  • Patent number: 4252698
    Abstract: An anti-yellowing additive is provided for environmentally acceptable stabilized vinyl chloride polymer compositions from which arsenic, beryllium, cadmium, lead, mercury, and thallium are substantially excluded, comprising at least one overbased sulfonate or phenolate compound of lithium, sodium, potassium, magnesium, calcium, strontium, barium, zinc, titanium, aluminum, zirconium, or tin, and a 1,3-diketone compound having 5 to 30 carbon atoms, which is a cyclic or open-chain 1,3-diketone or a lithium, sodium, potassium, magnesium, calcium, strontium, barium, zinc, aluminum, tin or zirconium salt thereof.
    Type: Grant
    Filed: April 17, 1979
    Date of Patent: February 24, 1981
    Assignee: Argus Chemical Corporation
    Inventors: Michio Ito, Yoshimitsu Numajiri, Seiji Kimura, Tetsuo Sekiguchi
  • Patent number: 4245056
    Abstract: A silicon peroxide selected from the formulas:(R').sub.4-n --Si--(OOR).sub.n (a) ##STR1## wherein n is an integer of 1-3; R is a t-octyl group in which a tertiary carbon atom is directly bonded to the peroxy group; and R' is selected from alkyl, phenyl, and alkenyl (provided n is not more than 2), and a carbon chain which forms a saturated heterocyclic ring with the silicon atom, each R' group having up to about 10 carbon atoms. Typical is trimethyl (2,4,4-trimethyl-2-pentylperoxy) silane. These molecules are useful as catalysts for curing polyester resins and are particularly advantageous as crosslinking agents for high density polyethylene in that crosslinking is effected at lower temperatures than required by the prior art.
    Type: Grant
    Filed: November 23, 1979
    Date of Patent: January 13, 1981
    Assignee: Argus Chemical Corporation
    Inventors: Lawrence A. Bock, Reidar Halle
  • Patent number: 4244848
    Abstract: An environmentally acceptable stabilizer composition is provided for enhancing the resistance to deterioration upon heating at 175.degree. C. of a vinyl chloride polymer from which lead, cadmium, mercury, thallium, and arsenic are substantially excluded, comprising (A) at least one zinc, alkali metal, or alkaline earth metal organic phosphate ester salt having per metal atom from one to a number equal to the valence of the metal of phosphate ester groups and from one to two organic groups per phosphate groups, the organic groups being alkyl, aryl, alkaryl, aralkyl, ether-interrupted allyl, or ether-interrupted aralkyl groups having from 1 to about 80 carbon atoms; and (B) at least one betadiketone compound having 5 to about 30 carbon atoms which is a cyclic or open-chain betadiketone or a zinc, alkali metal or alkaline earth metal salt thereof.A stabilized vinyl chloride polymer composition in which the environmentally acceptable composition is used as stabilizer is also provided.
    Type: Grant
    Filed: January 31, 1979
    Date of Patent: January 13, 1981
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Tetsuo Sekiguchi, Kenji Nakazawa
  • Patent number: 4239803
    Abstract: 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: Grant
    Filed: June 14, 1977
    Date of Patent: December 16, 1980
    Assignee: Argus Chemical Corporation
    Inventors: Toshio Ohzeki, Mitsuo Akutsu, Yutaka Nakahara, Tohru Haruna, Motonobu Minagawa, Masahiro Nonoyama
  • Patent number: 4233414
    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 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: Grant
    Filed: May 29, 1979
    Date of Patent: November 11, 1980
    Assignee: Argus Chemical Corporation
    Inventors: William E. Leistner, Motonobu Minagawa, Yutaka Nakahara, Tohru Haruna
  • Patent number: 4228306
    Abstract: Cyclic and acyclic phenylene substituted dialkyl peroxides most of which are in an acyclic polymeric form.
    Type: Grant
    Filed: November 1, 1978
    Date of Patent: October 14, 1980
    Assignee: Argus Chemical Corporation
    Inventors: Roger N. Lewis, Lawrence A. Bock
  • Patent number: 4224218
    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 sulfur-and nitrogen- free monocarboxylic acid or a phenol and (b) a metal salt of a phosphorous acid mono-ester in which the molar ratio of phosphorous acid mono-ester to metal is 1:1.Vinyl chloride polymer compositions stabilized with the above disclosed stabilizer composition are also disclosed.
    Type: Grant
    Filed: September 25, 1978
    Date of Patent: September 23, 1980
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Tetsuo Sekiguchi, Naoyasu Kurita, Yuji Sugawara
  • Patent number: 4224203
    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 sulfur--and nitrogen--free monocarboxylic acid or a phenol and (B) a metal P-hydrocarbonphosphonate having at least one to thirty carbon atoms in the hydrocarbon group.Vinyl chloride polymer compositions stabilized with the above disclosed stabilizer composition are also disclosed.
    Type: Grant
    Filed: September 5, 1978
    Date of Patent: September 23, 1980
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Tetsuo Sekiguchi, Naoyasu Kurita, Yuji Sugawara
  • Patent number: 4222931
    Abstract: 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: Grant
    Filed: December 8, 1977
    Date of Patent: September 16, 1980
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Yutaka Nakahara, Naohiro Kubota, Toshihiro Shibata
  • Patent number: 4219463
    Abstract: 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: Grant
    Filed: November 17, 1977
    Date of Patent: August 26, 1980
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Naohiro Kubota, Tohru Haruna, Toshihiro Shibata
  • Patent number: 4216294
    Abstract: Unsaturated polyester resin foams or cellular structures of varying low densities are prepared quickly at ambient temperatures from an admixture which comprises a liquid unsaturated curable polyester resin, an organic isocyanate compound, a suitable surfactant, an accelerator and a particular combination of peroxide curing agents, which also serves to initiate the release of gases that permit expansion of the resin in a controlled manner to obtain a foamed structure.
    Type: Grant
    Filed: May 30, 1978
    Date of Patent: August 5, 1980
    Assignee: Argus Chemical Corporation
    Inventors: Reidar Halle, Ronald L. Pastorino
  • Patent number: 4210577
    Abstract: 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.sup.. ; R.sub.
    Type: Grant
    Filed: December 8, 1977
    Date of Patent: July 1, 1980
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Yutaka Nakahara, Naohiro Kubota, Toshihiro Shibata
  • Patent number: 4198337
    Abstract: A silicon peroxide selected from the formulas:(R').sub.4-n --Si--(OOR).sub.n (a) ##STR1## wherein n is an integer of 1-3; R is a t-octyl group in which a tertiary carbon atom is directly bonded to the peroxy group; and R' is selected from alkyl, phenyl, and alkenyl (provided n is not more than 2), and a carbon chain which forms a saturated heterocyclic ring with the silicon atom, each R' group having up to about 10 carbon atoms. Typical is trimethyl (2,4,4-trimethyl-2-pentylperoxy) silane. These molecules are useful as catalysts for curing polyester resins and are particularly advantageous as crosslinking agents for high density polyethylene in that crosslinking is effected at lower temperatures than required by the prior art.
    Type: Grant
    Filed: September 25, 1978
    Date of Patent: April 15, 1980
    Assignee: Argus Chemical Corporation
    Inventors: Lawrence A. Bock, Reidar Halle
  • Patent number: 4197244
    Abstract: High density polyethylene is cross-linked with certain cyclic perketals including a group of novel cyclic perketals. Typical of the novel molecules is 3,6,6,9,9-pentamethyl-3-ethylacetate-1,2,4,5-tetraoxy cyclononane.
    Type: Grant
    Filed: July 31, 1978
    Date of Patent: April 8, 1980
    Assignee: Argus Chemical Corporation
    Inventors: Ronald L. Pastorino, Roger N. Lewis, Charles B. Abma
  • Patent number: 4189409
    Abstract: A novel process is provided for preparing a methylenebis(2-hydroxy-4-alkoxybenzophenone), comprising forming a novel 2-hydroxy-4-alkoxyacyloxymethylbenzophenone by a reaction of a 2-hydroxy-4-alkoxybenzophenone with a carboxylic acid and formaldehyde, and causing the 2-hydroxy-4-alkoxyacyloxymethylbenzophenone to react with a 2-hydroxy-4-alkoxybenzophenone in the presence of an acid catalyst.Both the acyloxymethylhydroxyalkoxybenzophenone and methylenebis(2-hydroxy-4-alkoxybenxophenone) which are prepared according to this invention are useful to prevent-degradation of organic materials, particularly as light stabilizers for synthetic resins.
    Type: Grant
    Filed: July 14, 1978
    Date of Patent: February 19, 1980
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata
  • Patent number: 4186151
    Abstract: A novel process is provided for preparing 5,5'-methylenebis(2-hydroxy-4-alkoxybenzophenone), comprising forming a novel 2-hydroxy-4-alkoxy-5-aminomethylbenzophenone by a reaction of a 2-hydroxy-4-alkoxybenzophenone with an amine and formaldehyde, and causing the 2-hydroxy-4-alkoxy-5-aminomethylbenzophenone to react with a 2-hydroxy-4-alkoxybenzophenone or to dimerize.Both the aminomethylhydroxyalkoxybenzophenone and the methylenebis (2-hydroxy-4-alkoxybenzophenone) which are prepared according to this invention are useful to prevent photo-degradation of organic materials, particularly as light stabilizers for synthetic resins.
    Type: Grant
    Filed: February 22, 1978
    Date of Patent: January 29, 1980
    Assignee: Argus Chemical Corporation
    Inventors: Naohiro Kubota, Toshihiro Shibata, Kazuo Sugibuchi
  • Patent number: 4174297
    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 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: Grant
    Filed: November 9, 1976
    Date of Patent: November 13, 1979
    Assignee: Argus Chemical Corporation
    Inventors: William E. Leistner, Motonobu Minagawa, Yutaka Nakahara, Tohru Haruna
  • Patent number: 4173599
    Abstract: 2,2,6,6-tetraalkyl-4-piperidyl ketones and ketals are provided, useful as stabilizers for organic polymeric materials, and having the general formula: ##STR1## wherein n are each 0 or 1 and are each the same;R is selected from the group consisting of hydrogen, alkyl having from one to about eighteen carbon atoms, and acryl ##STR2## R' being alkyl having from one to about eighteen carbon atoms; R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are selected from the group consisting of hydrogen and alkyl having from one to about eighteen carbon atoms;R.sub.6 is selected from the group consisting of hydrogen and O.sup..
    Type: Grant
    Filed: March 16, 1978
    Date of Patent: November 6, 1979
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata
  • Patent number: 4171298
    Abstract: New ortho-alkylhydroxybenzylpropanediol 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: Grant
    Filed: October 31, 1977
    Date of Patent: October 16, 1979
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Yutaka Nakahara, Masayuki Takahashi
  • Patent number: RE30338
    Abstract: A polyvinyl chloride resin stabilizer is provided having a high concentration of tin, in the range from about 20 to about 35% by weight, and a high concentration of sulfur, within the range from about 10 to about 25% sulfur, comprising .[.an.]. .Iadd.a di .Iaddend.organotin .Iadd.di .Iaddend.alpha- or beta-mercapto carboxylic acid ester and an organotin sulfide.Polyvinyl chloride resin compositions are also provided containing these stabilizers.
    Type: Grant
    Filed: August 28, 1978
    Date of Patent: July 15, 1980
    Assignee: Argus Chemical Corporation
    Inventor: Otto S. Kauder