Patents Assigned to Uniroyal Ltd.
  • Patent number: 4675044
    Abstract: Disclosed are derivatives of 3-aryl-5,6-dihydro-1,4,2-oxathiazines and their oxides for use as herbicides, fungicides, plant dessicants and defoliants in agricultural and biocidal applications. Also disclosed are methods of making these compounds.
    Type: Grant
    Filed: November 1, 1985
    Date of Patent: June 23, 1987
    Assignees: Uniroyal Chemical Company, Inc., Uniroyal Ltd.
    Inventors: Walter G. Brouwer, Allyn R. Bell, Allen R. Blem, Robert A. Davis
  • Patent number: 4670555
    Abstract: A compound having the structural formula ##STR1## where R.sup.1 and R.sup.2 are the same or different and are hydrogen; however, both R.sup.1 and R.sup.2 cannot be hydrogen if R.sup.3 and R.sup.4 are both hydrogen or if one of R.sup.3 and R.sup.4 is hydrogen and the other nitro; in addition R.sup.1 and R.sup.2 may be the same or different and may be fluorine, chlorine, bromine, iodine, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.7 -C.sub.9 aralkyl, phenyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkylsulfinyl, C.sub.7 -C.sub.9 aralkoxy, phenoxy, provided that if both R.sup.3 and R.sup.4 are hydrogen, then R.sup.1 and R.sup.2 cannot be 3-phenoxy and hydrogen; also R.sup.1 and R.sup.2 may be the same or different and may be phenylthio, phenylsulfonyl, alkali metal carboxylate, C.sub.2 -C.sub.5 alkoxycarbonyl, phenoxycarbonyl or --NR.sup.5 R.sup.6 ; R.sup.3 and R.sup.4 are the same or different and are C.sub.1 -C.sub.
    Type: Grant
    Filed: April 19, 1985
    Date of Patent: June 2, 1987
    Assignees: Uniroyal Chemical Company, Inc., Uniroyal Ltd.
    Inventors: Mark A. Dekeyser, Anupama Mishra, Richard C. Moore
  • Patent number: 4664694
    Abstract: A compound is disclosed having the structural formula ##STR1## where R is hydrogen, chlorine, bromine, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --CH.sub.2 COOH, --CH.sub.2 COO (C.sub.1 -C.sub.4 alkyl), --CH.sub.2 CONHN (C.sub.1 -C.sub.2 alkyl).sub.2, --CH.sub.2 CONR.sup.4 R.sup.5, --SPS(C.sub.1 -C.sub.4 alkoxy).sub.2 or --SPO(C.sub.1 -C.sub.4 alkoxy).sub.2 (C.sub.1 -C.sub.4 alkylthio).sub.2 ;R.sup.1, R.sup.2 and R.sup.3 are the same or different and are hydrogen, hydroxy, fluorine, chlorine, bromine, iodine, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.6 fluoroalkyl, C.sub.1 -C.sub.6 chloroalkyl, C.sub.1 -C.sub.6 fluoroalkoxy, C.sub.1 -C.sub.6 chloroalkoxy, C.sub.1 -C.sub.6 fluoroalkylthio, C.sub.1 -C.sub.6 chloroalkylthio, C.sub.7 -C.sub.9 aralkyl, phenyl, phenoxy, phenylthio, C.sub.2 -C.sub.5 alkoxycarbonyl, carboxy, nitro or cyano; andR.sup.4 and R.sup.5 are the same or different and are hydrogen or C.sub.1 -C.sub.
    Type: Grant
    Filed: April 24, 1985
    Date of Patent: May 12, 1987
    Assignees: Uniroyal Chemical Company, Inc., Uniroyal Ltd.
    Inventors: Walter G. Brouwer, Allen R. Blem
  • Patent number: 4636508
    Abstract: Novel 5-pyrimidinecarboxamides useful for regressing or inhibiting the growth of leukemia and tumors. The compounds have the formula: ##STR1## wherein R.sub.1 is hydrogen or an alkoxy group having from one to four carbon atoms;R.sub.2 is hydrogen; alkyl, aryl, aralkyl, allyl, aralkenyl or aralkynyl, the alkyl, alkenyl or alkynyl moieties of which have from one to six carbon atoms, or a carbohydrate residue;R.sub.3 is hydrogen, C.sub.1 -C.sub.4 alkyl or aryl;R.sub.
    Type: Grant
    Filed: April 22, 1985
    Date of Patent: January 13, 1987
    Assignees: Uniroyal Chemical Company, Inc., Uniroyal Ltd.
    Inventors: Arthur D. Brewer, John A. Minatelli
  • Patent number: 4634707
    Abstract: Novel 5-pyrimidinecarboxamides useful for regressing or inhibiting the growth of leukemia and tumors in mammals. The compounds have the formula: ##STR1## wherein: R is hydrogen, 2- or 3-halo, 4-fluoro, 2-methyl, 2- or 4-alkoxy, or 2- or 4-trifluoromethyl, and R.sub.1 is hydrogen; orR is 2-fluoro and R.sub.1 is 4-fluoro; orR is 2-methoxy and R.sub.1 is 5-methyl; andR.sub.2 and R.sub.3 are hydrogen atoms or carbohydrate residues; and,with the exception of the compound wherein R is 4-methoxy and R.sub.1 is hydrogen, the pharmacologically acceptable acid-addition salts thereof.
    Type: Grant
    Filed: February 8, 1985
    Date of Patent: January 6, 1987
    Assignees: Uniroyal Chemical Company, Uniroyal Ltd.
    Inventors: Arthur D. Brewer, John A. Minatelli
  • Patent number: 4634690
    Abstract: An organophosphorus compound having the structural formula ##STR1## where R is C.sub.1 -C.sub.4 alkyl; R.sup.1 is hydrogen or methyl; or R and R.sup.1 together are a diradical having the formula --SC(Y).dbd.Z--, where Y is halogen, hydrogen or C.sub.1 -C.sub.2 alkyl; and Z is nitrogen, CH, C(CH.sub.3) or C(C.sub.2 H.sub.5) with the proviso that if Y is hydrogen, Z cannot be CH; R.sup.2 is hydrogen, chlorine or bromine; R.sup.3 is methyl or ethyl; R.sup.4 is methoxy, ethoxy, --SCH.sub.3 or --SC.sub.2 H.sub.5 ; and X is oxygen or sulfur and their hydrochlorides is disclosed. These compounds are useful as insecticides or nematocides.In another aspect of this invention a method of controlling rice planthoppers is provided. In this method an insecticidally effective amount of a compound having the formula given above where R is C.sub.1 -C.sub.4 alkyl or benzyl; R.sup.1 is hydrogen or C.sub.1 -C.sub.3 alkyl; or R and R.sup.1 together are a diradical selected from the group consisting of --CH.dbd.CH--CH.dbd.
    Type: Grant
    Filed: July 18, 1984
    Date of Patent: January 6, 1987
    Assignees: Uniroyal Chemical Company, Inc., Uniroyal, Ltd.
    Inventors: Mark A. Dekeyser, Benjamin J. Pierce, Richard C. Moore, Winchester L. Hubbard
  • Patent number: 4569690
    Abstract: Disclosed are derivatives of 3-aryl-5,6-dihydro-1,4,2-oxathiazines and their oxides for use as herbicides, fungicides, plant dessicants and defoliants in agricultural and biocidal applications. Also disclosed are methods of making these compounds.
    Type: Grant
    Filed: September 12, 1983
    Date of Patent: February 11, 1986
    Assignees: Uniroyal, Inc., Uniroyal, Ltd.
    Inventors: Walter G. Brouwer, Allyn R. Bell, Allen R. Blem, Robert A. Davis
  • Patent number: 4545735
    Abstract: The pump has a pumping chamber with a deflectable diaphragm member and fluid inlet and outlet passages. A deflectable valve flap is disposed across the fluid inlet passage and another flexible valve flap is disposed across the fluid outlet passage. Movement of the flexible valve flaps is responsive to movement of the flexible diaphragm member, reciprocation of which establishes alternate sequential suction and discharge conditions. An air chamber provided in the pump receives outside air through an air vent opening and also communicates with the pump discharge passage through a bleed hole when the outlet passage is closed by the outlet valve flap. The outlet valve flap is also deflectable to a position where it closes the bleed hole. Under this arrangement, continuous siphoning of fluid through the pump after the pump has been shut down is obviated.
    Type: Grant
    Filed: August 17, 1984
    Date of Patent: October 8, 1985
    Assignee: Uniroyal, Ltd.
    Inventor: Horst O. H. Ims
  • Patent number: 4490532
    Abstract: Hydrogen chloride is passed into p-xylene and acetaldehyde to form bis-1-chloroethyl ether; the latter is converted to 2-(1-chloroethyl)-1,4-dimethylbenzene by the action of sulfuric acid and hydrogen chloride. Alkali metal hydrogen sulfide in aqueous methanol or ethanol converts the 2-(1-chloroethyl)-1,4-dimethylbenzene to alpha,2,5-trimethylbenzenemethanethiol; the sodium salt of the latter reacted with 2-chloropyridine-1-oxide yields 2-[1-(2,5-dimethylphenyl)ethylthio]pyridine-1-oxide which is then oxidized with hydrogen peroxide and alkali metal tungstate or tungstic acid to form 2-[1-(2,5-dimethylphenyl)ethylsulfonyl]pyridine-1-oxide.
    Type: Grant
    Filed: July 28, 1980
    Date of Patent: December 25, 1984
    Assignee: Uniroyal Ltd.
    Inventor: John W. Harris
  • Patent number: 4464538
    Abstract: Disclosed is a method for synthesizing dihydro-1,4-dithiins by the reaction of an acyloin or a halocarbonyl compound with an organic thiosulfate.
    Type: Grant
    Filed: May 3, 1983
    Date of Patent: August 7, 1984
    Assignee: Uniroyal Ltd.
    Inventor: Arthur D. Brewer
  • Patent number: 4394155
    Abstract: Compounds of the following formula are effective as premergence herbicides: ##STR1## wherein R and R.sup.1 may be the same or different and are C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, phenyl or halogen, provided that R or R.sup.1 is not halogen if attached in the 3- position of the pyridine ring, and R or R.sup.1 may further be hydrogen provided that one of them is one of the recited moieties other than hydrogen; R.sup.2 is hydrogen, halogen, methyl or ethyl; R.sup.3 is phenyl or phenyl substituted with halogen, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, or nitro; and n is 1 or 2.
    Type: Grant
    Filed: February 5, 1981
    Date of Patent: July 19, 1983
    Assignees: Uniroyal, Inc., Uniroyal Ltd.
    Inventors: Howard L. Plant, Steven E. Cantor, Arthur M. Doweyko, Mark A. Dekeyser, Allyn R. Bell
  • Patent number: 4359579
    Abstract: 2-[(2-hydroxyethyl)thio]-3-oxo-N-phenylbutanamide, which is an intermediate useful in the manufacture of the fungicide, 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide, is made by reaction of di-(2-hydroxyethyl) disulfide with acetoacetanilide in its ionized form.
    Type: Grant
    Filed: August 24, 1981
    Date of Patent: November 16, 1982
    Assignee: Uniroyal, Ltd.
    Inventors: George Liebermann, Frederick M. M. Hager
  • Patent number: 4319033
    Abstract: A method of making certain 2,3-dihydro-1,4-dithiins of the following formula by the action of alpha-hydroxyketones (acyloins) of 1,2-dithiols: ##STR1## wherein R.sup.1 and R.sup.2 are hydrogen or alkyl having 1 to 6 carbon atoms or are joined together to form a ring with 3 or 4 methylene groups, and R.sup.3 and R.sup.4 are hydrogen or the same or different alkyl groups having 1 to 10 carbon atoms, which alkyl groups may be substituted with lower alkoxy groups.
    Type: Grant
    Filed: March 26, 1981
    Date of Patent: March 9, 1982
    Assignee: Uniroyal Ltd.
    Inventors: Allan K. S. Tsai, Duncan D. Lennox, Arthur D. Brewer
  • Patent number: 4312972
    Abstract: Interpolymerizate of polyurethane-forming ingredients (polyol, polyisocyanate) and free radical addition polymerizable monomers, at least one of which contains an hydroxyl group (e.g., styrene plus 2-hydroxyethyl methacrylate). The interpolymer is prepared in the presence of a catalyst for polyurethane formation and a free radical addition polymerization catalyst. Product is homogeneous and insoluble. System is useful in reaction injection molding processes.
    Type: Grant
    Filed: March 26, 1981
    Date of Patent: January 26, 1982
    Assignee: Uniroyal Ltd.
    Inventor: Som N. Khanna
  • Patent number: 4299789
    Abstract: In extrusion apparatus of the type having a generally cylindrical roller, a stationary die head surface confronting the roller and defining therewith an extrudate chamber, and means for rotating the roller to force material through the chamber to an extrudate shaping orifice defined by the roller and a downstream portion of the die head, a bearing pad is interposed between the roller and the die head. The roller is biased against the bearing pad so that the pad serves to space the roller from the die head to accurately control clearance between the die head and roller at the extrudate shaping orifice.
    Type: Grant
    Filed: December 5, 1979
    Date of Patent: November 10, 1981
    Assignee: Uniroyal Ltd.
    Inventor: George G. Giesbrecht
  • Patent number: 4288584
    Abstract: A stable electret made of a resinous polymer of a branched alpha-olefin [e.g., poly(4-methyl-1-pentene)] having a degree of crystallinity of at least 20%.
    Type: Grant
    Filed: October 30, 1978
    Date of Patent: September 8, 1981
    Assignee: Uniroyal Ltd.
    Inventor: Anupama Mishra
  • Patent number: 4276422
    Abstract: Regulation of the growth of plant life, including herbicidal, defoliant or desiccant effects, may be accomplished with certain 2,3-dihydro-1,4-dithiin 1,1,4,4-tetroxides of the formula ##STR1## wherein the R's have various values such as hydrogen, alkyl, etc. Certain of the compounds, such as 2,3-dihydro-5,6-dimethyl-1,4-dithiin 1,1,4,4-tetroxide, are new chemicals, and are useful as pre- and post-emergent herbicides, and in harvest aid procedures, such as defoliation/desiccation of various crops, including cotton and potatoes.
    Type: Grant
    Filed: March 7, 1977
    Date of Patent: June 30, 1981
    Assignees: Uniroyal, Inc., Uniroyal Ltd.
    Inventors: Arthur D. Brewer, Robert W. Neidermyer, William S. McIntire
  • Patent number: 4265798
    Abstract: Potassium salt of 2-pyrrolidinone is used as a catalyst to cyclotrimerize an organic diisocyanate, yielding a mixture of monomeric cyclotrimerized product (isocyanurate) and oligomers thereof, soluble in common organic solvents and vinyl monomers. The catalyst can be used to make one-shot isocyanurate-crosslinked polyurethanes. Prepolymers and moisture-curing coating compositions can also be prepared.
    Type: Grant
    Filed: February 11, 1980
    Date of Patent: May 5, 1981
    Assignee: Uniroyal Ltd.
    Inventor: Anupama Mishra
  • Patent number: 4263442
    Abstract: 2,3-Dihydro-5,6-diphenyl-1,4-oxathiin is prepared by reacting benzoin and 2-mercaptoethanol in an alkanol solvent of 2 to 8 carbon atoms and an acidic catalyst. The use of alcohol solvent in lieu of aromatic solvents gives much greater purity with much better yields.
    Type: Grant
    Filed: June 9, 1980
    Date of Patent: April 21, 1981
    Assignee: Uniroyal Ltd.
    Inventors: Michael A. Puttock, Ethel E. Felauer, Bruce A. Graham
  • Patent number: 4257517
    Abstract: A scraper bar for use with conveyor belting and the like to clean such belting of material adhering to its surface. The scraper bar consists of a layer of hard abrasion-resistant pellets embedded in an elastomer to form an elastomer/pellet matrix. An additional layer of elastomer is cast to the matrixed layer to provide a surface for attaching the scraper to its support when in service. Embedded in the layer of unmatrixed elastomer is an insert of particle board, chipboard, plywood or fibreglass reinforced plastic sheeting. The insert prevents bowing of the scraper bar due to differential shrinkage between the layer of matrixed elastomer and pellets and the supporting layer of elastomer.
    Type: Grant
    Filed: December 6, 1976
    Date of Patent: March 24, 1981
    Assignee: Uniroyal Ltd.
    Inventors: Edwin J. MacPherson, Peter J. Alderson, Douglas A. Skinner