Patents Assigned to Adeka Argus Chemical Co., Ltd.
  • Patent number: 4615912
    Abstract: Hydrophilic inorganic materials are provided with a hydrophobic surface by treatment with a metal glycolate compound having the formula: ##STR1## wherein: Me is Sn, Ti, Zr or Al;when Me is Sn, Ti or Zr, m is 1, and when Me is Al, m is 0;R is alkyl having from about eight to about fifty carbon atoms;X.sub.1 and X.sub.2 are independently selected from the group consisting of --R.sub.1, --OR.sub.1, --OCOR.sub.1, --SR.sub.1, --S(CH.sub.2).sub.n COOR.sub.1, --OSO.sub.2 --R.sub.1, --SR.sub.2 OCOR.sub.1, ##STR2## X.sub.1 and X.sub.2 can be combined to form ##STR3## R.sub.1 is selected from the group consisting of alkyl having from one to about eighteen carbon atoms; alkenyl having from three to about eighteen carbon atoms; cycloalkyl having from five to about eight carbon atoms; and aryl and alkaryl having from six to about eighteen carbon atoms;R.sub.2 is alkylene having from one to about fifty carbon atoms;R.sub.
    Type: Grant
    Filed: August 1, 1984
    Date of Patent: October 7, 1986
    Assignee: Adeka Argus Chemical Co., Ltd.,
    Inventors: Tetsuyu Inoue, Kouji Tsuruga, Masashi Harada
  • Patent number: 4540728
    Abstract: Polymers of diallyl-1,3,5-triazino-4-(2,2,6,6-tetramethyl piperidyl) amines are provided, having a molecular weight within the range from about 800 to about 20,000, and derived from the monomer: ##STR1## wherein: R.sub.1 is selected from the group consisting of hydrogen; oxyl; alkyl and hydroxyalkyl having from one to about eighteen carbon atoms; alkylaryl having from seven to about eighteen carbon atoms; epoxy alkyl having from three to about eighteen carbon atoms; and acyl having from two to about eighteen carbon atoms;Y is selected from the group consisting of ##STR2## where R.sub.2 and R.sub.3 are hydrogen or alkyl having from one to about eight carbon atoms and n is 0 or 1;Z is selected from the group consisting of ##STR3## in which R.sub.4, R.sub.5 and R.sub.
    Type: Grant
    Filed: September 9, 1983
    Date of Patent: September 10, 1985
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Yutaka Nakahara, Ryoji Kimura
  • Patent number: 4529760
    Abstract: Oligomers of 2,2,6,6-tetramethylpiperidinol polycarboxylic acid esters are provided having the formula: ##STR1## wherein: Z is the residue of an aliphatic or aromatic or nitriloaliphatic or hydroxy aliphatic polycarboxylic acid having from three to six carboxylic acid groups and from one to thirty carbon atoms; ##STR2## wherein R.sub.3 is hydrogen, alkyl and hydroxyalkyl having from one to about twenty carbon atoms; cycloalkyl having from six to about twenty carbon atoms; aryl having from six to about twenty carbon atoms; or cycloalkylene with the N in the ring and having from two to five carbon atoms;R is alkylene having from two to about twelve carbon atoms; cycloalkylene having from three to about twelve carbon atoms; phenylene having from six to about twenty carbon atoms; mixed alkylenecycloalkylene or alkylene phenylene or oxyalkylene having from two to about twelve carbon atoms; ##STR3## wherein R.sub.4 is alkyl having from one to about six carbon atoms;R.sub.
    Type: Grant
    Filed: November 1, 1983
    Date of Patent: July 16, 1985
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: William E. Leistner, Motonobu Minagawa, Yutaka Nakahara, Tohru Haruna, Atsushi Nishimura
  • Patent number: 4525506
    Abstract: Polyhydric alcohol ethers of 2,2,6,6-tetramethyl-4-piperidone ketals are provided, having the formula: ##STR1## wherein: R is selected from the group consisting of hydrogen, alkyl having from one to about eight carbon atoms, and alkyleneoxyalkylene, each alkylene having from two to about eight carbon atoms;R.sub.1 is selected from the group consisting of hydrogen and alkyl having from one to about four carbon atoms;R.sub.2 is selected from the group consisting of hydrogen; oxyl O; alkyl, hydroxy alkyl and epoxyalkyl having from one to about eighteen carbon atoms; acyl having from one to about eighteen carbon atoms; cycloalkyl having from three to about eighteen carbon atoms; phenyl; phenalkyl and alkylphenyl having from seven to about twenty-four carbon atoms; andn is a number from 3 to 6as well as synthetic resin compositions having an improved resistance to deterioration and containing such compounds.
    Type: Grant
    Filed: March 25, 1983
    Date of Patent: June 25, 1985
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata, Ryozo Arata
  • Patent number: 4500663
    Abstract: N,N,N-tris(2,2,6,6-tetramethyl-4-piperidone ketal)-1,3,5-triazines are provided, having the formula: ##STR1## wherein: R.sub.1 is selected from the group consisting of hydrogen and alkyl having from one to about four carbon atoms; andR.sub.2 is selected from the group consisting of hydrogen; oxyl O; alkyl, hydroxy alkyl and epoxyalkyl having from one to about eighteen carbon atoms; alkanoyl having from one to about eighteen carbon atoms; cycloalkyl having from three to about eighteen carbon atoms; phenyl; phenalkyl and alkylphenyl having from seven to about twenty-four carbon atoms; as well as synthetic resin compositions having an improved resistance to deterioration and containing such compounds.
    Type: Grant
    Filed: March 25, 1983
    Date of Patent: February 19, 1985
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata, Ryozo Arata
  • Patent number: 4499220
    Abstract: Copolymer 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 copolymers of a maleic or fumaric acid ester containing a 2,2,6,6-tetraalkyl piperidyl group in the alcohol group of the formula: ##STR1## wherein ##STR2## R.sub.2 is alkyl or R.sub.1 ; X is ##STR3## R.sub.6 is lower alkyl; R.sub.3 is hydrogen or alkyl;R.sub.4 is hydrogen or methyl;R.sub.5 is alkylene;Y is ##STR4## R.sub.7 is alkylene; and at least one monomer selected from the group consisting of aliphatic carboxylic acid vinyl ester having from two to eight carbon atoms; alkyl vinyl ethers having from one to eighteen carbon atoms; triallyl isocyanurate; pinene; and tricyclo-(5.2.1.0.sup.2.6)-decene-3; and synthetic resin compositions having improved light stability comprising per 100 parts by weight of resin from 0.001 to 5 parts by weight of the polymeric light stabilizer.
    Type: Grant
    Filed: May 20, 1982
    Date of Patent: February 12, 1985
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata
  • Patent number: 4491643
    Abstract: Bis(2,2,6,6-tetramethylpiperidyl-1,3,5-triazinyl)-spirodiamines and spiroglycol ethers are provided, having the formula: ##STR1##
    Type: Grant
    Filed: January 9, 1984
    Date of Patent: January 1, 1985
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Motonobu Minagawa, Yutaka Nakahara, Toshihiro Shibata, Etsuo Tobita
  • Patent number: 4487900
    Abstract: Polymers of diallyl 4-(2,2,6,6-tetramethyl piperidyl) amines are provided, having a molecular weight within the range from about 800 to about 20,000, and derived from the monomer ##STR1## wherein: R is selected from the group consisting of hydrogen, oxyl, alkyl and hydroxyalkyl having from one to about eighteen carbon atoms; alkylaryl having from seven to about eighteen carbon atoms; epoxy alkyl having from three to about eighteen carbon atoms and acyl having from two to about eighteen carbon atoms, as well as stabilized synthetic resin compositions having an improved resistance to deterioration by light and containing such a polymer.
    Type: Grant
    Filed: September 9, 1983
    Date of Patent: December 11, 1984
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Yutaka Nakahara, Ryoji Kimura
  • Patent number: 4487887
    Abstract: Polymers of diallyl amino-4-(2,2,6,6-tetramethyl piperidyl) carboxylic acid esters and amides are provided, having a molecular weight within the range from about 800 to about 20,000, and derived from a monomer having the formula: ##STR1## wherein: R is alkylene or alkyleneoxy having from one to about six carbon atoms and m is 0 or 1;R.sub.1 is selected from the group consisting of hydrogen; oxyl; alkyl and hydroxyalkyl having from one to about eighteen carbon atoms; alkylaryl having from seven to about eighteen carbon atoms; epoxy alkyl having from three to about eighteen carbon atoms; and acyl having from two to about eighteen carbon atoms; andY is selected from the group consisting of ##STR2## where R.sub.2 and R.sub.3 are hydrogen or alkyl having from one to about eight carbon atoms and n is 0 or 1;Z is selected from the group consisting of ##STR3## in which R.sub.4, R.sub.5 and R.sub.
    Type: Grant
    Filed: September 9, 1983
    Date of Patent: December 11, 1984
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Yutaka Nakahara, Ryoji Kimura
  • Patent number: 4481317
    Abstract: Hindered bisphenol diphosphonites are provided having the structure: ##STR1## wherein: A is selected from the group consisting of thio sulfur --S--; oxy oxygen --O--; alkylidene having from one to about ten carbon atoms; cycloalkylidene having from about four to about eight carbon atoms; and phenylalkylidene having from seven to about twelve carbon atoms;R is selected from the group consisting of alkyl having from one to about eighteen carbon atoms; cycloalkyl having from three to about twelve carbon atoms; and aralkyl having from seven to about twelve carbon atoms;R.sub.1 is selected from the group consisting of hydrogen; alkyl having from one to about eighteen carbon atoms; cycloalkyl having from three to about twelve carbon atoms; and aralkyl having from seven to about twelve carbon atoms;R.sub.2 is selected from the group consisting of ##STR2## as well as synthetic resin compositions having an enhanced resistance to deterioration by heat and light comprising a synthetic resin and such phosphonites.
    Type: Grant
    Filed: June 7, 1983
    Date of Patent: November 6, 1984
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Yutaka Nakahara, Tohru Haruna, Etsuo Tobita
  • Patent number: 4477616
    Abstract: Tetra-2,2,6,6-tetramethyl-4-piperidinyl)-3-methyl-5-(1',2'-biscarboxylate)- ethyl-cyclohexane or 3-cyclohexene-1,2-dicarboxylates are provided having the formula (I) or (II): ##STR1## wherein: R.sub.1 is selected from the group consisting of hydrogen, --O, alkyl, hydroxy alkyl and epoxyalkyl having from one to about eighteen carbon atoms, acyl having from one to about eighteen carbon atoms, cycloalkyl having from three to about eighteen carbon atoms; phenyl; phenalkyl and alkylphenyl having from seven to about twenty-four carbon atoms;R.sub.2 is lower alkyl having from one to about six carbon atoms; andX is selected from the group consisting of: ##STR2## as well as stabilized synthetic resin compositions comprising such piperidinyl compounds.
    Type: Grant
    Filed: March 3, 1983
    Date of Patent: October 16, 1984
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Motonobu Minagawa, Yutaka Nakahara, Toshihiro Shibata
  • Patent number: 4469828
    Abstract: Alkylthiopropionyl hydrazino triazines are provided having the formula: ##STR1## wherein: R is alkyl having from one to about fifty carbon atoms;X is ##STR2## where R.sub.1 is selected from the group consisting of hydrogen, alkyl having from one to about fifty carbon atoms; and ##STR3## where R.sub.2 is selected from the group consisting of hydrogen, O and alkyl hydroxyalkyl, epoxy alkyl and acyloxy alkyl having from one or two to about eight carbon atoms;when X is O, A is selected from the group consisting of alkylene having from two to about twenty carbon atoms, cycloalkylene having from about five to about eight carbon atoms and phenylene;when X is ##STR4## A is selected from the group consisting of a direct linkage, alkylene having from one to about twenty carbon atoms, cycloalkylene having from five to about eight carbon atoms; phenylene; and ##STR5## where R.sub.
    Type: Grant
    Filed: November 22, 1982
    Date of Patent: September 4, 1984
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Motonobu Minagawa, Tohru Haruna, Masayuki Takahashi
  • Patent number: 4468488
    Abstract: Poly(piperidylamine) alkanes represented by the Formula (I) or (II): ##STR1## and synthetic resin compositions having improved resistance to deterioration by light containing such compounds.
    Type: Grant
    Filed: February 28, 1983
    Date of Patent: August 28, 1984
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Motonobu Minagawa, Yutaka Nakahara, Toshihiro Shibata, Ryozo Arata
  • Patent number: 4427816
    Abstract: Stabilizer compositions for halogen-containing polymers are provided composed of a .beta.-diketone as well as metal and organotin enolate salts thereof; and a hydrotalcite having the general formula:Mg.sub.1-x Al.sub.x (OH).sub.2 A.sub.x/2.mH.sub.2 Owhereinx is a number from 0 to 0.5;A is CO.sub.3.sup.= or SO.sub.4.sup.=, andm is a number representing the number of H.sub.2 O in the molecule.The stabilizer compositions are effective in enhancing the resistance to deterioration by heat and light of halogen-containing polymers and especially polyvinyl halide resins. The .beta.-diketone and hydrotalcite in these compositions exhibit a synergistic stabilizing effectiveness superior to either alone in like amount.
    Type: Grant
    Filed: January 29, 1982
    Date of Patent: January 24, 1984
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Toshihiro Aoki, Yoshio Iida
  • Patent number: 4423174
    Abstract: Synthetic resin compositions of improved resistance to deterioration by heat and light are provided containing a 2,2,6,6-tetramethyl piperidyl ether having the formula: ##STR1## The compounds of the invention can be prepared by the reaction of the 2,2,6,6-tetramethyl piperidyl alcohol R.sub.1 -OH with (poly) trimethylol alkane, (poly) pentaerthritol, or an alcohol containing an oxetane ring, to form the ether.The etherification is carried out by the conventional method, for example, by the reaction of R.sub.1 -OH with the organic sulfonate of the above-mentioned alcohols, or by the reaction of R.sub.1 -OH with the halogenated above-mentioned alcohols in the presence of an alkali or acid acceptor.The compounds where n is equal to 2 or more can be prepared by chain opening polymerization of the corresponding compound containing the oxetane ring.
    Type: Grant
    Filed: July 26, 1982
    Date of Patent: December 27, 1983
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Motonobu Minagawa, Naohiro Kubota, Ryoji Kimura
  • Patent number: 4418196
    Abstract: A process is provided for preparing triacetone amine (2,2,6,6-tetramethyl-4-oxo piperidine) by reacting acetone and/or an acid condensate of acetone with ammonia in the presence of at least one catalyst selected from the group consisting of organotin halides, 1,3,5,2,4,6-triazatriphosphorin hexahalides and cyanuric halides.
    Type: Grant
    Filed: August 23, 1982
    Date of Patent: November 29, 1983
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Yutaka Nakahara, Naohiro Kubota, Bunji Hirai, Tohru Haruna
  • Patent number: 4416797
    Abstract: Chlorinated organic compounds having their resistance to deterioration (when heated, exposed to light or water, or in contact with certain metals such as iron and aluminum) enhanced by a 1,3-dicarbonyl compound having the formula: ##STR1## wherein: R.sub.1 is selected from the group consisting of hydrogen, hydrocarbon groups having from one to about eighteen carbon atoms and such groups substituted with one or more groups selected from the group consisting of halogen, hydroxy, alkoxy OR.sub.1, ester COOR.sub.1, alkyl and alkoxycarbonyl alkyl having from one to about eighteen carbon atoms;R.sub.2 is selected from the group consisting of hydrocarbon groups having from one to about eighteen carbon atoms and such groups substituted with one or more groups selected from the group consisting of halogen, hydroxy, alkoxy OR.sub.1, ester COOR.sub.1, alkyl and alkoxycarbonyl alkyl having from one to about eighteen carbon atoms;R.sub.
    Type: Grant
    Filed: February 19, 1981
    Date of Patent: November 22, 1983
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Motonobu Minagawa, Tetsuyu Inoue, Naoyasu Kurita
  • Patent number: 4415689
    Abstract: Synthetic resin compositions having an improved resistance to deterioration upon exposure to light comprising a 2,2,6,6-tetramethyl piperidinyl triazine.
    Type: Grant
    Filed: September 7, 1982
    Date of Patent: November 15, 1983
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Motonobu Minagawa, Yutaka Nakahara, Toshihiro Shibata
  • Patent number: 4415688
    Abstract: Poly(piperidylamine) alkanes represented by the Formula (I) or (II): ##STR1## R is selected from the group consisting of: --NH.sub.2 ; ##STR2## and synthetic resin compositions having improved resistance to deterioration by light containing such compounds.
    Type: Grant
    Filed: November 22, 1982
    Date of Patent: November 15, 1983
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Motonobu Minagawa, Yutaka Nakahara, Toshihiro Shibata, Ryozo Arata
  • Patent number: 4405736
    Abstract: 2,2,6,6-Tetramethyl-4-piperidyl spiro aliphatic ethers are provided, useful as stabilizers for organic polymeric materials.
    Type: Grant
    Filed: June 9, 1981
    Date of Patent: September 20, 1983
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Naohiro Kubota, Toshihiro Shibata, Kazuo Sugibuchi, Yutaka Nakahara