Patents Assigned to Argus Chemical Corporation
  • Patent number: 4107136
    Abstract: 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: Grant
    Filed: October 6, 1976
    Date of Patent: August 15, 1978
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Yutaka Nakahara, Tohru Haruna
  • Patent number: 4105629
    Abstract: 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: Grant
    Filed: October 13, 1976
    Date of Patent: August 8, 1978
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Yutaka Nakahara, Tohru Haruna
  • Patent number: 4105627
    Abstract: Improved clarity and resistance to deterioration on heating of polyvinyl fluoride and vinyl chloride polymers is obtained by employing a stabilizer composition consisting essentially of (A) a heterocyclic nitrogen compound having as part of a 5 or 6 membered heterocyclic ring the group ##STR1## in which R is hydrogen, aryl, or alkyl having 1 to 12 carbon atoms, and X is oxygen or sulfur, and (B) one or more 1,2-epoxides, organic phosphites, or stannous tin, zinc, magnesium, aluminum, potassium, sodium, calcium, strontium, or barium salts of non-nitrogenous monocarboxylic acids having from 6 to 24 carbon atoms or hydrocarbon-substituted phenols having from about 10 to about 30 carbon atoms.
    Type: Grant
    Filed: September 20, 1976
    Date of Patent: August 8, 1978
    Assignee: Argus Chemical Corporation
    Inventors: Tetsuo Sekiguchi, Masami Abe, Kouji Tsuruga, Nobuhide Tominaga
  • Patent number: 4105625
    Abstract: 2,2,6,6-TETRAMETHYL-4-PIPERIDYL CARBOXYLIC ACID ESTERS OF ALIPHATIC DI- OR TRI- CARBOXYLIC ACIDS ARE PROVIDED, USEFUL AS LIGHT STABILIZERS FOR ORGANIC POLYMERIC MATERIALS, AND HAVING THE GENERAL FORMULA: ##STR1## wherein: R.sub.1 is selected from the group consisting of ##STR2## R.sub.2 is CH.sub.3 or C.sub.2 H.sub.5 ; a is selected from the group consisting of 2 and 3;M is selected from the group consisting of 1, 2, 3 and 4; andZ is a divalent ot trivalent aliphatic radical carrying from two to three ##STR3## groups, and can include from one to four hydroxyl groups OH.
    Type: Grant
    Filed: February 22, 1977
    Date of Patent: August 8, 1978
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata
  • Patent number: 4104217
    Abstract: 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: Grant
    Filed: January 24, 1977
    Date of Patent: August 1, 1978
    Assignee: Argus Chemical Corporation
    Inventors: William E. Leistner, Motonobu Minagawa, Yutaka Nakahara, Tohru Haruna
  • Patent number: 4102815
    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: November 8, 1976
    Date of Patent: July 25, 1978
    Assignee: Argus Chemical Corporation
    Inventors: Ronald L. Friedman, deceased, Roger N. Lewis
  • Patent number: 4102858
    Abstract: 2,2,6,6-TETRAMETHYL-4-PIPERIDYL THIOCARBOXYLATES AND AMINOCARBOXYLATES ARE PROVIDED HAVING THE GENERAL FORMULA: ##STR1## wherein: M.sub.1, M.sub.3, AND M.sub.4 ARE NUMBERS FROM 0 TO 1;m.sub.2 is a number from 1 to 2;n.sub.1 is a number from 0 to 2;n.sub.2 is a number from 0 to 3;n.sub.3 is a number from 0 to 2;R.sub.1 is selected from the group consisting of alkyl, aralkyl, cycloalkyl and 2,2,6,6-tetramethyl-4-piperidyl;R.sub.2 is selected from the group consisting of alkyl, cycloalkyl, alkylaryl, aralkyl, and hydroxy-substituted such radicals;R.sub.1 and R.sub.2 have from one to about twenty carbon atoms;X is hydrogen or O;Y.sub.1 and Y.sub.2 are bivalent linking radicals having from one to about 20 carbon atoms, and selected from the group consisting of alkylene and cycloalkylene; and amino-substituted such radicals;Q is selected from the group consisting of SR.sub.
    Type: Grant
    Filed: September 20, 1976
    Date of Patent: July 25, 1978
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata
  • Patent number: 4101508
    Abstract: 2,2,6,6-TETRAMETHYL-4-PIPERIDYL ESTERS OF BICYCLIC HEPTANE AND OCTANE CARBOXYLIC ACIDS ARE PROVIDED, USEFUL AS STABILIZERS FOR ORGANIC POLYMERIC MATERIALS, AND HAVING THE GENERAL FORMULA: ##STR1## R.sub.1 is selected from the group consisting of hydrogen and O; R.sub.2 is selected from the group consisting of alkyl; alkenyl; cycloalkyl; aryl; alkaryl; aralkyl;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; and a + b is 1, 2, 3 or 4; and"ZEE" is a bicyclic heptane or octane ring having from seven to eight ring carbon atoms.
    Type: Grant
    Filed: October 26, 1976
    Date of Patent: July 18, 1978
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata
  • Patent number: 4096114
    Abstract: Organic phosphites are provided having at least one 2,2,6,6-tetramethyl piperidyl substituent attached at the 4-position to phosphorus through oxygen, and at least one polyol or polyphenol group, which are superior light and heat stabilizers for organic polymeric mterials such as polyethylene, polypropylene, polyvinyl chloride, acrylonitrile-butadiene-styrene terpolymers, polyamides, polystyrene, and similar polymers.
    Type: Grant
    Filed: August 16, 1976
    Date of Patent: June 20, 1978
    Assignee: Argus Chemical Corporation
    Inventors: Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata, Kazuo Sugibuchi
  • Patent number: 4082812
    Abstract: An organic peroxide of the formula ##STR1## wherein X and Y are both selected from the same one of the following two subparagraphs:(a) each of X and Y is the same and is a peroxy alkyl group of the structure --OOR in which R is a t-alkyl group of 4-8 carbon atoms;(b) X is chlorine and Y has the structure ##STR2##
    Type: Grant
    Filed: April 25, 1977
    Date of Patent: April 4, 1978
    Assignee: Argus Chemical Corporation
    Inventor: Donald W. Wood
  • Patent number: 4080364
    Abstract: Stabilizer mixtures that are capable of enhancing the resistance of polyolefins to degradation as a result of exposure to light and air, particularly at elevated temperatures, are obtained by reacting an .alpha.-olefin with an ester of a mercaptocarboxylic acid and a polyhydric alcohol, forming a reaction product of unknown structure containing thioether groups and carboxylic acid ester groups.
    Type: Grant
    Filed: September 27, 1976
    Date of Patent: March 21, 1978
    Assignee: Argus Chemical Corporation
    Inventors: Otto S. Kauder, Lawrence R. Brecker
  • Patent number: 4076918
    Abstract: A process is provided for preparing cellulose thiocyanate by direct reaction of cellulose with thiocyanic acid in the presence of dimethyl formamide, or dimethyl sulfoxide, at elevated temperatures, the thiocyanic acid being formed in situ from a thiocyanate salt and sulfuric acid. The product, cellulose thiocyanate, has a carbon content of from 38% to 44.4%, a nitrogen content of from 0.1% to 6.3%, a sulfur content of 0.23% to 14.5%, and is noninflammable and self-extinguishing.
    Type: Grant
    Filed: February 12, 1975
    Date of Patent: February 28, 1978
    Assignee: Argus Chemical Corporation
    Inventors: Shaul Gladstone, Clifton R. Neumoyer
  • Patent number: 4071677
    Abstract: Asymmetrical organic diacyl peroxide polymerization initiators having enhanced initiator efficiency and characterized by the presence of an acyclic acyl group of four or more carbon atoms having bromo or halo substitution at the alpha carbon atom, the other acyl group being different and heterosubstituted. However, when the alpha-halosubstituted acyl group is branched chain the other acyl group may be hydrocarbon.
    Type: Grant
    Filed: March 4, 1977
    Date of Patent: January 31, 1978
    Assignee: Argus Chemical Corporation
    Inventor: Donald W. Wood
  • Patent number: 4069239
    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 polymerization of methyl methacrylate.
    Type: Grant
    Filed: March 7, 1977
    Date of Patent: January 17, 1978
    Assignee: Argus Chemical Corporation
    Inventors: Roger N. Lewis, Ronald L. Pastorino, James F. Wilts
  • Patent number: 4063013
    Abstract: Novel tertiary alkyl peresters of tertiary hydroperoxides are used as polymerization initiators wherein the peresters are characterized by the tertiary alkyl group of the acid moiety having at least two alkyl groups of two or more carbon atoms and the tertiary alkyl group of the hydroperoxide has at least five carbon atoms. Typical is the polymerization of certain vinyl monomers such as vinyl chloride.
    Type: Grant
    Filed: April 28, 1977
    Date of Patent: December 13, 1977
    Assignee: Argus Chemical Corporation
    Inventors: Ronald L. Friedman, Roger N. Lewis
  • Patent number: 4057567
    Abstract: Novel tertiary alkyl peresters of tertiary hydroperoxides are used as polymerization initiators wherein the peresters are characterized by the tertiary alkyl group of the acid moiety having at least two alkyl groups of two or more carbon atoms and the tertiary alkyl group of the hydroperoxide has at least five carbon atoms. Typical is the polymerization of certain vinyl monomers such as vinyl chloride.
    Type: Grant
    Filed: February 20, 1973
    Date of Patent: November 8, 1977
    Assignee: Argus Chemical Corporation
    Inventors: Ronald L. Friedman, Roger N. Lewis
  • Patent number: 4056561
    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 vulcanization of silicone rubber.
    Type: Grant
    Filed: March 7, 1977
    Date of Patent: November 1, 1977
    Assignee: Argus Chemical Corporation
    Inventors: Roger N. Lewis, Ronald L. Pastorino, James F. Wilts
  • Patent number: 4051167
    Abstract: Aliphatic peroxyester polymerization initiators whose thermal stability is controlled by a bromine or chlorine substituent on the carbon atom in the alpha position relative to the carbonyl group in the acid moity of the perester. The initiators show increased efficiency for the polymerization of methyl methacrylate, styrene, ethylene, and in curing unsaturated polyester resins. Typical is 1,1,3,3-tetramethyl butyl peroxy 2-chlorolaurate.
    Type: Grant
    Filed: December 19, 1975
    Date of Patent: September 27, 1977
    Assignee: Argus Chemical Corporation
    Inventor: Roger N. Lewis
  • Patent number: 4051310
    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 polymerization of methyl methacrylate.
    Type: Grant
    Filed: June 16, 1976
    Date of Patent: September 27, 1977
    Assignee: Argus Chemical Corporation
    Inventors: Roger N. Lewis, Ronald L. Pastorino, James F. Wilts
  • Patent number: 4032605
    Abstract: Asymmetrical organic diacyl peroxide polymerization initiators having enhanced initiator efficiency and characterized by the presence of an acyclic acyl group of four or more carbon atoms having bromo or halo substitution at the alpha carbon atom, the other acyl group being different and heterosubstituted. However, when the alpha-halosubstituted acyl group is branched chain the other acyl group may be hydrocarbon.
    Type: Grant
    Filed: December 6, 1971
    Date of Patent: June 28, 1977
    Assignee: Argus Chemical Corporation
    Inventor: Donald W. Wood