The Dow Chemical Company

Thomas C Klingler

Ritchie A Wessling

Donald L Schmidt

Christian T Goralski

Dale S Gibbs

Victor E Meyer

Demetrius Urchick

Warner Jensen, Jr

Paul A Wolf

Novel polymers having high activity as cationic surface-active agents are prepared by the addition polymerization of ethylenically unsaturated aromatic sulfonium salts, e.g., ##STR1## When such polymers are heated and/or dried, they are irreversibly converted to inert, nonionic residues without the elimination of odorous by-products. The novel sulfonium salt polymers having relatively low molecular weight and low charge density are particularly useful as surfactants or emulsifiers in the emulsion polymerization of ethylenically unsaturated monomers such as styrene, butadiene, alkyl acrylates and the like. The polymers having high molecular weight and high charge density are useful as thickeners and flocculants.

Addition polymerizable aromatic sulfonium salts and polymers thereof

Aqueous acidic compositions which contain a combination of an organic polymer having a bound latent source of thiolate ions, such as isothiouronium groups and an organic polymer having bound cationic onium groups, such as sulfonium groups, or a polymer containing both kinds of groups can be cured in the wet state by raising the pH to above about 9 at a temperature from about 0.degree. C. to about 100.degree. C.

Aqueous compositions containing organic polymers curable at low

Novel isothiouronium salts are herein described which correspond to the formula ##STR1## wherein R and R' are each independently hydrocarbyl or inertly-substituted hydrocarbyl of at least 4 carbon atoms; R.sub.1 -R.sub.4 are each independently alkyl or hydroxyalkyl of 1 to 4 carbon atoms, or R.sub.1 and R.sub.3 are joined to form a 5- or 6-membered heterocyclic ring; n is 0 or 1; and A.sup..crclbar. is an inert neutralizing anion. The isothiouronium salts are surprisingly effective dispersing agents and are used in forming electrodepositable latexes.

Novel isothiouronium salts

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.

Cyclic sulfonium ylids

Compounds of the formula ##STR1## wherein: EACH R individually is H, OH or C.sub.1 -C.sub.4 alkoxy;

Process for producing hydroxyarylpolymethylenesulfonium salts

Aryl dibromonitromethyl sulfones, new compounds, wherein aryl is phenyl or lower alkyl phenyl, are effective as antimicrobials at a concentration of about 100 parts per million.

Aryl dibromonitromethyl sulfones

Dibromonitromethyl methyl sulfone is effective as a slimicide at a concentration of about 100 parts per million.

Dibromonitromethyl methyl sulfone slimicide

Modified cationic latexes are prepared from nonionic or cationic latexes having particles containing chemically bound epoxide groups at or near the particle surface by reacting the latex with a nucleophile such as dimethyl sulfide and an acid such as acetic acid to form a latex having stabilizing onium ions chemically bound to the particle at or near the particle surface.

Method for preparing cationic latexes

The compounds of the formula ##SPC1## In which R independently is hydrogen, lower alkyl, lower alkoxy, halo or trifluoromethyl; x is 1 to 2; n is 1 to 3, and R.sub.1 and R.sub.2 independently are hydrogen, lower alkyl or phenyl and together with the nitrogen atom form a heterocycle which may contain an oxygen atom as a hetero atom. The compounds are prepared by reacting the corresponding N-substituted-1-(arylthio)methanesulfonamide with small, incremental amounts up to substantially equimolar of 30% hydrogen peroxide in glacial acetic acid at 65.degree.-70.degree. C., to obtain the sulfinyl compound, or substantially two equimolar proportions of 30% hydrogen peroxide in glacial acetic acid at reflux temperature to obtain the sulfonyl compound, and recovering the corresponding sulfinyl or sulfonyl product.

N-substituted-1-(arylsulfinyl and arylsulfonyl)methanesulfonamides

The compounds of the formula ##SPC1## In which R is lower alkyl, lower alkoxy or halo, x is an integer from 0 to 2, n is an integer from 0 to 3, Y is halo and R.sub.1 and R.sub.2 independently are hydrogen, lower alkyl, phenyl or substituted phenyl, or, together with the nitrogen atom, form a heterocyclic ring also containing up to one oxygen atom in the heterocycle. The compounds in which x is 0 are prepared by adding chlorine or bromine to a 1-arylthiomethanesulfonamide in the presence of pyridine to form the 1-arylthio-1, 1-dihalomethanesulfonamide. The compounds in which x is 1 or 2 is prepared by adding sodium hypochlorite or sodium hypobromite to a 1-(arylsulfinyl)methane-sulfonamide or a 1-(arylsulfonyl)methanesulfonamide to form the 1-(arylsulfinyl)-1,1-dihalomethanesulfonamide or 1-(arylsulfonyl)-1,1-dihalomethanesulfonamide, respectively. The compounds are useful as antimicrobial agents.

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Midland, MI, United States of America

Thomas C Klingler