Patents Represented by Attorney L. Wayne White
  • Patent number: 4020030
    Abstract: Water soluble or water dispersible reaction products are produced by reacting (1) an epoxy resin having an epoxy equivalent weight of at least about 500 with (2) an organic sulfide in the presence of (3) a protic acid having a dissociation constant greater than 1 .times. 10.sup.-.sup.5. Such reaction products can be used alone as coating compositions or can be blended with various resins which will react with pendent hydroxy groups on the above reaction product upon heating and thereby form a cross-linked product. The melamine resins are examples of suitable such "cross-linkers".
    Type: Grant
    Filed: February 24, 1975
    Date of Patent: April 26, 1977
    Assignee: The Dow Chemical Company
    Inventors: Robert F. Harris, Nancy B. Tefertiller
  • Patent number: 4016225
    Abstract: Mixtures of (1) a quaternary ammonium salt(s) and (2) 1,4-diazabicyclo[2.2.2]octane are novel catalysts in the process of reacting an alkali metal phenate, pyridinate or pyrimidiate with an O,O-dialkyl phosphorochloridothioate or O-alkyl phenylphosphonochloridothioate to produce the corresponding phosphorothioates and phenylphosphonothioates. The process is conducted under alkaline conditions in a liquid reaction medium. As an example, O,O-diethyl 0-(3,5,6-trichloro-2-pyridyl)phosphorothioate is prepared in excellent yields and purity by reacting sodium 3,5,6-trichloropyridinate with O,O-diethyl phosphorochloridothioate in a stirred methylene chloride-water reaction medium in the presence of a catalytic amount of benzyltriethylammonium chloride and 1,4-diazabicyclo[2.2.2]octane.
    Type: Grant
    Filed: July 31, 1975
    Date of Patent: April 5, 1977
    Assignee: The Dow Chemical Company
    Inventors: Lorraine M. Kroposki, Masao Yoshimine
  • Patent number: 4016192
    Abstract: Ethylenically-unsaturated products are obtained by (a) reacting acrylic acid and 2-oxazoline or a 2-alkyl or aryl-2-oxazoline in an inert liquid reaction medium and (b) recovering the desired product from (a) by heating the reaction mixture under reduced pressure to strip away the liquid diluent and volatile components, thus leaving the desired product as a non-volatile residue. The reaction products can be cross-linked by conventional techniques (e.g. freeradical initiation) to form useful coatings and adhesives. For example, the product produced by heating equal molar amounts of acrylic acid and 2-ethyl-2-oxazoline in benzene gave an ethylenically-unsaturated oligomeric product having a number average molecular weight of 253 and a weight average molecular weight of 460 in approximately 95 percent yield.
    Type: Grant
    Filed: December 30, 1974
    Date of Patent: April 5, 1977
    Assignee: The Dow Chemical Company
    Inventors: Donald A. Tomalia, Bruce P. Thill, Thomas W. Regulski
  • Patent number: 4016171
    Abstract: 2-Vinyl-2-oxazolines are prepared in the novel process comprising reacting (1) an N-(2-haloalkyl)-3-halopropionamide with (2) at least 2 equivalents of an inorganic base per mole of (1). The process is conducted under substantially anhydrous conditions and in the presence of an alkylene glycol or a polyalkylene glycol.
    Type: Grant
    Filed: September 14, 1972
    Date of Patent: April 5, 1977
    Assignee: The Dow Chemical Company
    Inventors: Bruce P. Thill, Janet N. Paige
  • Patent number: 4014880
    Abstract: The reaction of 2-oxazolines with 1,2- or 1,3-alkylenediamines to form 2-imidazolines or 1,4,5,6-tetrahydropyrimidines is catalyzed by Lewis acids.
    Type: Grant
    Filed: February 9, 1976
    Date of Patent: March 29, 1977
    Assignee: The Dow Chemical Company
    Inventors: William Dowd, Peter W. Owen
  • Patent number: 4014891
    Abstract: The title compounds are prepared in excellent yields by reacting an alkali aromatic mercaptide with bromochloromethane in the presence of a quaternary ammonium salt having ten or more carbon atoms. Normally the chlorobromomethane is used in excess as the liquid reaction medium. Reaction temperatures are normally selected in the range of from about 20.degree. to about 65.degree. C.
    Type: Grant
    Filed: January 17, 1975
    Date of Patent: March 29, 1977
    Assignee: The Dow Chemical Company
    Inventors: Christian T. Goralski, George A. Burk
  • Patent number: 4013480
    Abstract: Novel cellulosic sizing agents are described. They are ring-opened aziridinyl homopolymers of ##EQU1## wherein R.sub.1 and R.sub.2 are hydrogen or lower alkyl; R.sub.3 is hydrogen or methyl; R.sub.4 is an organic hydrophobic group (e.g., C.sub.8 -C.sub.24 alkyl radical); and X is oxygen or amido nitrogen. The above homopolymers can also be blended with cationic starch to form useful sizing compositions. These sizing agents are normally employed as aqueous emulsions. E.g., paper having excellent sizing properties was prepared from a paper pulp containing a mixture of cationic starch and poly[stearyl 3-(1-aziridinyl)propionate].
    Type: Grant
    Filed: January 10, 1974
    Date of Patent: March 22, 1977
    Assignee: The Dow Chemical Company
    Inventors: Lewis E. Chumbley, Lawrence L. Sams, II, Russell T. McFadden, Juan Longoria, III, Donald A. Tomalia, Robert J. Thomas, James W. Lalk
  • Patent number: 4011160
    Abstract: Novel polymers are described herein which are particularly useful in removing phenolics from waste streams. The polymers are prepared by reacting an oxazoline or oxazine (preferably 2-methyl or ethyl-2-oxazoline) with a cross-linked vinylaromatic polymer bearing pendant halomethyl groups on the aromatic rings. Macroporous beads prepared by reacting cross-linked chloromethylated polystyrene with 2-methyl and/or 2-ethyl-2-oxazoline are particularly useful embodiments in removing phenolics from aqueous waste streams and are used to remove phenolics (e.g. tannins) and other color-bodies from bleached Kraft pulp effluent.
    Type: Grant
    Filed: December 9, 1975
    Date of Patent: March 8, 1977
    Assignee: The Dow Chemical Company
    Inventors: Thomas A. Chamberlin, Norman L. Madison
  • Patent number: 4011376
    Abstract: Novel products corresponding to the formula ##STR1## are produced by reacting an allyl halide (e.g., allyl chloride) or a vinylbenzyl halide (e.g., vinylbenzyl chloride) with an oxazoline or an oxazine. The novel compounds are polymerizable monomers and can be used to complex phenols.
    Type: Grant
    Filed: March 3, 1975
    Date of Patent: March 8, 1977
    Assignee: The Dow Chemical Company
    Inventors: Donald A. Tomalia, Elizabeth A. Zubritsky
  • Patent number: 4007197
    Abstract: Quaternary ammonium salts and sterically unhindered, nucleophilic, tertiary amines are novel cocatalysts which are used in the process of reacting an alkali metal phenate, pyridinate or pyrimidinate with an O,O-dialkylphosphorochloridothioate or O-alkyl phenylphosphonochloridothioate to produce the corresponding phosphorothioates and phenylphosphonothioates. The process is conducted under alkaline conditions in a liquid reaction medium.
    Type: Grant
    Filed: June 10, 1975
    Date of Patent: February 8, 1977
    Assignee: The Dow Chemical Company
    Inventors: Harold H. Freedman, Stanley D. McGregor, Masao Yoshimine, Lorraine M. Kroposki
  • Patent number: 4001147
    Abstract: Novel polymers are described herein which are particularly useful in removing phenolics from waste streams. The polymers are prepared by reacting an oxazoline or oxazine (preferably 2-methyl or ethyl-2-oxazoline) with a cross-linked vinylaromatic polymer bearing pendant halomethyl groups on the aromatic rings. Macroporous beads prepared by reacting cross-linked chloromethylated polystyrene with 2-methyl and/or 2-ethyl-2-oxazoline are particularly useful embodiments in removing phenolics from aqueous waste streams and are used to remove phenolics (e.g. tannins) and other color-bodies from bleached Kraft pulp effluent.
    Type: Grant
    Filed: March 3, 1975
    Date of Patent: January 4, 1977
    Assignee: The Dow Chemical Company
    Inventors: Thomas A. Chamberlin, Norman L. Madison
  • Patent number: 4001154
    Abstract: The adhesion of hydrophobic coatings to ferrous or siliceous articles is enhanced by first coating said articles with a primer comprising (a) a water-soluble cross-linkable polymer bearing a plurality of carboxyl groups, (b) a water-soluble cyclic sulfonium zwitterion or melamine cross-linking agent, and (c) a silane. The novel primers are thermally-curable film-forming compositions which are particularly useful in coating glass and ferrous articles.
    Type: Grant
    Filed: September 4, 1973
    Date of Patent: January 4, 1977
    Assignee: The Dow Chemical Company
    Inventor: Donald L. Schmidt
  • Patent number: 3996237
    Abstract: New esters are described having the formula ##STR1## wherein R is a chemical bond or an inert linking group such as alkylene, oxa-alkylene, thia-alkylene, arylene, alkenylene or the like, R' and R" are H or lower alkyl and n is 2-3. They are made by the reaction of a bis-oxazoline or -oxazine with an equimolar amount of an acrylic acid: ##STR2## The compounds (I) are acrylic esters and are polymerizable and copolymerizable by the same general techniques used with other acrylic esters, thus producing solid resins useful as molding and coating materials. The oxazoline and oxazine rings in such resins are reactive with carboxyl groups; hence, the resins can be mixed with carboxy-containing polymers to form mixtures that readily cure upon mmold heat treatment to form hard, water-resistant and solvent-resistant, infusible resins.
    Type: Grant
    Filed: July 17, 1974
    Date of Patent: December 7, 1976
    Assignee: The Dow Chemical Company
    Inventor: Donald A. Tomalia
  • Patent number: 3996147
    Abstract: The corrosion of metal surfaces in contact with aqueous acid cleaning solutions is inhibited by sulfonium salt corresponding to the formula ##STR1## wherein n is 1 or 2; R.sub.1 is an electron withdrawing group; R.sub.2 is a hydrocarbyl radical or inertly-substituted hydrocarbyl radical of up to about 24 carbon atoms; R.sub.3 is alkyl of from 1 to 4 carbon atoms, inertly-substituted alkyl of 2-4 carbon atoms, allyl, phenyl or inertly-substituted phenyl; or R.sub.2 and R.sub.3 are joined to form a 5- or 6-membered heterocyclic ring; and A.sup.- is a compatible anion. These sulfonium salts are effective corrosion inhibitors even in the presence of ferric ions.
    Type: Grant
    Filed: August 8, 1973
    Date of Patent: December 7, 1976
    Assignee: The Dow Chemical Company
    Inventors: William J. Settineri, Wayne W. Frenier, James H. Oswald
  • Patent number: 3990843
    Abstract: A method of bleaching cotton is described herein which comprises contacting said cotton with a bleaching solution of chlorine monoxide in an inert liquid solvent (e.g. methyl chloroform). Bleaching occurs very rapidly by this method and the cotton fibers undergo very little if any degradation.
    Type: Grant
    Filed: August 5, 1974
    Date of Patent: November 9, 1976
    Assignee: The Dow Chemical Company
    Inventors: Thomas A. Chamberlin, L. Wayne White
  • Patent number: 3972887
    Abstract: Quaternary ammonium salts are novel catalysts in the process of reacting an alkali metal phenate, pyridinate or pyrimidinate with an O,O-dialkyl phosphorochloridothioate or O-alkyl phenylphosphonochloridothioate to produce the corresponding phosphorothioates and phenylphosphonothioates. The process is conducted under alkaline conditions in a liquid reaction medium. As an example, O,O-diethyl O-(3,5,6-trichloro-2-pyridyl)-phosphorothioate is prepared in excellent yields and purity by reacting solid particulate sodium 3,5,6-trichloropyridinate with O,O-diethyl phosphorochloridothioate dissolved in a stirred methylene chloride reaction medium in the presence of a catalytic amount of benzyltriethylammonium chloride.
    Type: Grant
    Filed: June 12, 1975
    Date of Patent: August 3, 1976
    Assignee: The Dow Chemical Company
    Inventor: Harold H. Freedman
  • Patent number: 3971730
    Abstract: 1,1,1-Trichloroethane is prepared in the novel process comprising reacting by contacting chlorine monoxide with CH.sub. 3 --CH.sub.2 Cl and/or CH.sub.3 --CHCl.sub.2. The reaction is conducted in liquid phase and at a temperature of from about -20.degree. to about 80.degree.C.
    Type: Grant
    Filed: September 9, 1974
    Date of Patent: July 27, 1976
    Assignee: The Dow Chemical Company
    Inventors: Gerald L. Kochanny, Jr., Thomas A. Chamberlin
  • Patent number: 3969414
    Abstract: Novel sulfonium compounds are described herein which correspond to the formula ##SPC1##The sulfonium compounds are useful corrosion inhibitors in acidic cleaning solutions.
    Type: Grant
    Filed: February 18, 1975
    Date of Patent: July 13, 1976
    Assignee: The Dow Chemical Company
    Inventors: Wayne W. Frenier, William J. Settineri
  • Patent number: 3969360
    Abstract: The reaction between the alkali metal halopyridinates with the lower alkyl esters of .alpha.-chloro or bromo acetic acid (or propionic acid) to form the corresponding O-alkylated halopyridinates is catalyzed by quaternary ammonium salts. For example, methyl .alpha.-(6-chloropyridinyloxy)acetate was prepared in excellent yield by reacting sodium 6-chloropyridinate with excess methyl .alpha.-chloroacetate in the presence of 2 mole percent of benzyl triethyl ammonium chloride.
    Type: Grant
    Filed: December 23, 1974
    Date of Patent: July 13, 1976
    Assignee: The Dow Chemical Company
    Inventor: Harold H. Freedman
  • Patent number: 3962235
    Abstract: The title compounds are prepared by contacting in liquid phase a 2-alkyl-2-oxazoline or oxazine with a t-alkyl hypochlorite. As an example, 2-chloromethyl-2-oxazoline was prepared in approximately 95 percent yield by contacting a substantially equimolar amount of 2-methyl-2-oxazoline with t-butyl hypochlorite for 19 hours at 23.degree.C in the dark. The process was conducted in carbon tetrachloride solution.
    Type: Grant
    Filed: January 25, 1974
    Date of Patent: June 8, 1976
    Assignee: The Dow Chemical Company
    Inventor: Thomas A. Chamberlin