Patents Represented by Attorney L. Wayne White
  • Patent number: 4220550
    Abstract: Sulfide-containing scale is removed from metal surfaces by contacting the encrusted surface with an aqueous acid cleaning solution having an aldehyde (e.g., formaldehyde) dissolved or dispersed in the acid in an amount sufficient to prevent the evolution of hydrogen sulfide gas.
    Type: Grant
    Filed: December 6, 1978
    Date of Patent: September 2, 1980
    Assignee: The Dow Chemical Company
    Inventors: Wayne W. Frenier, Michael D. Coffey, James D. Huffines, Donald C. Smith
  • Patent number: 4211873
    Abstract: Monochloromethylpyridines are produced by reacting 2- or 4-methylpyridine oxides with phosphoryl chloride in the presence of an organic base. One product, 2-chloromethylpyridine, is formed by reacting 2-picoline-N-oxide with phosphoryl chloride in the presence of triethylamine.
    Type: Grant
    Filed: July 25, 1978
    Date of Patent: July 8, 1980
    Assignee: The Dow Chemical Company
    Inventors: R. Garth Pews, Mezzie L. Ash
  • Patent number: 4210552
    Abstract: Certain sulfonium salts are herein described which are useful corrosion inhibitors in aqueous acidic cleaning solutions, even in the presence of ferric ions.
    Type: Grant
    Filed: September 28, 1978
    Date of Patent: July 1, 1980
    Assignee: The Dow Chemical Company
    Inventors: Wayne W. Frenier, William J. Settineri
  • Patent number: 4203900
    Abstract: A cyclodehydration reaction is described for preparing 2-oxazolines which comprises reacting in liquid phase (a) an N-(2-hydroxyalkyl)carboxamide with (b) a small but catalytic amount of an iron-containing compound. The reaction is normally conducted at elevated temperatures (e.g., 180.degree.-200.degree. C.) and under reduced pressure. Both 2-H- and 2-substituted-2-oxazolines are prepared by this process. For example, 2-H-2-oxazoline and 2-ethyl-2-oxazoline were prepared in 83.1 percent and 90.2 percent yields, respectively, by contacting the appropriate N-(2-hydroxyethyl)carboxamide with ferrous chloride tetrahydrate at temperatures of approximately 180.degree.-200.degree. C./50 mm Hg. Under these conditions, the oxazoline product and water were codistilled from the reaction mixture essentially as fast as they were formed.
    Type: Grant
    Filed: January 3, 1977
    Date of Patent: May 20, 1980
    Assignee: The Dow Chemical Company
    Inventor: Mark E. Kaiser
  • Patent number: 4196298
    Abstract: Novel cyclic sulfonium ylids corresponding to the formula ##STR1## wherein R is a hydrocarbylene radical (or a hydrocarbylene radical whose chain length is interrupted by an atom of oxygen or sulfur) of from 2 to about 20 carbon atoms, are useful as cross-linking agents for carboxyl-containing polymers. The compounds are conveniently prepared by reacting phenacyltetrahydrothiophenium bromide with the corresponding hydrocarbylene diisocyanate in the presence of a strong base (e.g. sodium hydride) and anhydrous tetrahydrofuran.
    Type: Grant
    Filed: November 6, 1978
    Date of Patent: April 1, 1980
    Assignee: The Dow Chemical Company
    Inventors: Thomas C. Klingler, Donald L. Schmidt
  • Patent number: 4195154
    Abstract: The title compounds are of the formula: ##STR1## wherein R is a chemical bond, oxygen, sulfur, alkylene or alkylidene; W is hydrogen or a (--CR.sub.1 R.sub.2 --CR.sub.3 R.sub.4 --NHR.sub.5) group with the proviso that at least two W groups are (--CH.sub.1 R.sub.2 --CR.sub.3 R.sub.4 --NHR.sub.5) groups; wherein R.sub.1 -R.sub.4 are each independently hydrogen, lower alkyl or hydroxy-substituted lower alkyl; R.sub.5 is hydrogen or a ##STR2## group, wherein R.sub.6 is hydrogen, hydrocarbyl or inertly substituted hydrocarbyl; X, Y and Z are each independently inert substituents; m and p are each independently integers of from zero to four, inclusive; n is an integer of from zero to three, inclusive; q is a number of from zero to about ten; and M is alkylene or alkylidene. They are conveniently prepared by reacting a 2-oxazoline of the formula: ##STR3## with a polyhydric polyphenol of the formula: ##STR4## in the presence of certain metal salt catalysts (e.g. zinc acetate).
    Type: Grant
    Filed: August 15, 1977
    Date of Patent: March 25, 1980
    Assignee: The Dow Chemical Company
    Inventors: Mark E. Kaiser, Harry A. Smith
  • Patent number: 4189543
    Abstract: Compounds of formulas I and II are heat-activated catalysts used in making polyurethanes. ##STR1## wherein R, R.sub.1, and R.sub.2 are each independently H, hydrocarbyl or an inertly-substituted hydrocarbyl; R.sub.3 and R.sub.4 are each independently hydrocarbyl or an inertly-substituted hydrocarbyl; and X is an anion. Upon heating, Compounds I and II catalyze the reaction and may release gaseous by-products which cause the resulting polyurethane compound to foam. For example, the catalyst, t-butyl imidazole-N-carboxylate, when heated to 120.degree. C., catalyzes the reaction between a polyol and a polyisocyanate to give a foamed polyurethane which cured in 16 minutes.
    Type: Grant
    Filed: August 21, 1978
    Date of Patent: February 19, 1980
    Assignee: The Dow Chemical Company
    Inventors: George A. Doorakian, Lawrence G. Duquette, Philip W. McGraw
  • Patent number: 4177216
    Abstract: The trisubstituted (2,5-dihydroxyphenyl)phosphonium hydroxide inner salts and their hydrolyzed derivatives are novel latent catalysts for promoting reaction between vicinal epoxides and phenols and/or carboxylic acids (or anhydrides). Precatalyzed epoxy resins are easily prepared using such catalysts.
    Type: Grant
    Filed: September 26, 1978
    Date of Patent: December 4, 1979
    Assignee: The Dow Chemical Company
    Inventors: George A. Doorakian, Lawrence G. Duquette
  • Patent number: 4175196
    Abstract: Novel onium surfactants are described which correspond to the formula X[(CH.sub.2 CH.sub.2 O--.sub.m CH.sub.2 --R--CHR'--Q.sup..sym. A.sup..crclbar. ].sub.n, wherein X is an n-valent hydrophobic radical derived by the removal of n-atoms of active hydrogen from an organic compound; m is one or more; R is a divalent aromatic hydrocarbon radical of from 6 to about 14 carbon atoms, the chain-length of which may be interrupted by oxygen or sulfur atoms; R' is hydrogen or methyl and is methyl only when R is m- or p-phenylene; Q.sup..sym. is a quaternized atom of nitrogen or phosphorus or a tertiary atom of sulfur; A.sup..crclbar. is a compatible anion; and n is from 1 to 5. The following compound is an example C.sub.9 H.sub.19 --C.sub.6 H.sub.4 --O--CH.sub.2 CH.sub.2 O--.sub.15 CH.sub.2 --C.sub.6 H.sub.4 --CH.sub.2 --S.sup..sym. --CH.sub.3).sub.2 Cl.sup..crclbar.. The novel surfactants are prepared in two steps.
    Type: Grant
    Filed: April 12, 1978
    Date of Patent: November 20, 1979
    Assignee: The Dow Chemical Company
    Inventors: Robert F. Harris, Earl H. Wagener
  • Patent number: 4171420
    Abstract: The trisubstituted (2,5-dihydroxyphenyl)phosphonium hydroxide inner salts and their hydrolyzed derivatives are novel latent catalysts for promoting reaction between vicinal epoxides and phenols and/or carboxylic acids (or anhydrides). Precatalyzed epoxy resins are easily prepared using such catalysts.
    Type: Grant
    Filed: September 26, 1978
    Date of Patent: October 16, 1979
    Assignee: The Dow Chemical Company
    Inventors: George A. Doorakian, Lawrence G. Duquette
  • Patent number: 4170591
    Abstract: Metal salt complexes of aziridine and 2-alkylaziridines in solution isomerize at temperatures between 20.degree.-70.degree. C. to form aziridine dimer chelates. The chelates are biologically active compounds and are chemical intermediates in the preparation of free aziridine dimers.
    Type: Grant
    Filed: May 9, 1973
    Date of Patent: October 9, 1979
    Assignee: The Dow Chemical Company
    Inventor: John M. Motes
  • Patent number: 4159382
    Abstract: Picolylamines are prepared by reacting (a) cyanopyridine with (b) hydrogen in the presence of a catalytic amount of (c) a palladium on .gamma.-alumina catalyst. The reaction is normally conducted under autogenous or superatmospheric pressure at a temperature of from 20.degree. C. to about 75.degree. C. in a lower alkanol (e.g., isopropanol) as the reaction medium.
    Type: Grant
    Filed: June 28, 1978
    Date of Patent: June 26, 1979
    Assignee: The Dow Chemical Company
    Inventor: Philip E. Garrou
  • Patent number: 4152342
    Abstract: Novel polyamines are disclosed which consist essentially of linear chains of the formula ##STR1## WHEREIN R is H or the acyl group of a fatty acid or an alkylsulfonic acid and n is a number about 6-22. Of the n units in the chain, in about 0 to 50% R is an acyl group of about 20-150 carbon atoms, in about 5-75% R is an acyl group of about 1-18 carbon atoms and in about 10-90% R is H.The compounds are made by appropriate partial acylation of the corresponding polyethylenepolyamine or by (a) polymerizing a 2-alkyl-2-oxazoline and then partially hydrolyzing and reacylating the polymer thus obtained. They are useful as surfactants, especially as detergents in lubricating oils.
    Type: Grant
    Filed: April 11, 1977
    Date of Patent: May 1, 1979
    Assignee: The Dow Chemical Company
    Inventors: Jacqueline S. Kelyman, George A. Paul
  • Patent number: 4147866
    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: February 22, 1978
    Date of Patent: April 3, 1979
    Assignee: The Dow Chemical Company
    Inventors: Harold H. Freedman, Stanley D. McGregor, Masao Yoshimine, Lorraine M. Kroposki
  • Patent number: 4144211
    Abstract: Novel solid complexes of 2-oxazoline and 2-oxazine polymers and halogens, interhalogens or pseudo-halogens are prepared by contacting a poly-2-oxazoline or poly-2-oxazine whose backbone comprises a plurality of ring-opened units of an oxazoline or oxazine monomer of the general formula ##STR1## wherein R and R.sub.1 -R.sub.4 are each independently hydrogen, alkyl, aralkyl, phenyl or inertly-substituted phenyl and n is zero or one with a halogen, interhalogen or pseudo-halogen. The complexes are soluble in a variety of conventional solvents (e.g., water, methylene chloride, acetonitrile, methanol, tetrahydrofuran and isopropanol).
    Type: Grant
    Filed: September 6, 1977
    Date of Patent: March 13, 1979
    Assignee: The Dow Chemical Company
    Inventors: Thomas A. Chamberlin, Sonia W. Bangs
  • Patent number: 4132706
    Abstract: The trisubstituted (2,5-dihydroxyphenyl)phosphonium hydroxide inner salts and their hydrolyzed derivatives are novel latent catalysts for promoting reaction between vicinal epoxides and phenols and/or carboxylic acids (or anhydrides). Precatalyzed epoxy resins are easily prepared using such catalysts.
    Type: Grant
    Filed: April 5, 1976
    Date of Patent: January 2, 1979
    Assignee: The Dow Chemical Company
    Inventors: George A. Doorakian, Lawrence G. Duquette
  • Patent number: 4131633
    Abstract: Certain phosphorus-containing compounds are described herein which are novel latent catalysts for promoting the reaction between vicinal epoxides and phenols and/or carboxylic acids (or anhydrides). Precatalyzed epoxy resins are easily prepared using such catalysts.
    Type: Grant
    Filed: April 11, 1977
    Date of Patent: December 26, 1978
    Assignee: The Dow Chemical Company
    Inventors: George A. Doorakian, Dennis L. Schmidt, Martin C. Cornell, III
  • Patent number: 4131619
    Abstract: The title compound is prepared in high yield and purity from toluene in a process comprising the steps of:(a) reacting by contacting toluene with sulfur trioxide in an anhydrous chlorinated hydrocarbon medium, to thereby form a solution of toluenesulfonic acid in the chlorinated hydrocarbon medium;(b) reacting by contacting chlorine gas with the product from step (a) in the presence of a catalytic amount of iodine, to thereby form a solution of chlorotoluenesulfonic acid in the chlorinated medium; and(c) reacting by contacting chlorosulfonic acid with the product from step (b), to thereby form a solution of chlorotoluenesulfonyl chloride in the chlorinated medium.As an example, the title compound is obtained in a yield more than 90 percent based on toluene, using 1,2-dichloroethane as the reaction medium.
    Type: Grant
    Filed: March 22, 1978
    Date of Patent: December 26, 1978
    Assignee: The Dow Chemical Company
    Inventor: R. Garth Pews
  • Patent number: 4101438
    Abstract: Certain sulfonium salts are herein described which are useful corrosion inhibitors in aqueous acidic cleaning solutions, even in the presence of ferric ions.
    Type: Grant
    Filed: March 22, 1976
    Date of Patent: July 18, 1978
    Assignee: The Dow Chemical Company
    Inventors: Wayne W. Frenier, William J. Settineri
  • Patent number: RE30283
    Abstract: Certain sulfonium salts are herein described which are useful corrosion inhibitors in aqueous acidic cleaning solutions, even in the presence of ferric ions.
    Type: Grant
    Filed: February 13, 1979
    Date of Patent: May 27, 1980
    Assignee: The Dow Chemical Company
    Inventors: Wayne W. Frenier, William J. Settineri