The Dow Chemical Company

Earl H Wagener

Ritchie A Wessling

Dale S Gibbs

Robert F Harris

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. In step 1, various nonionic surfactants are reacted with certain chloromethylated aromatics in the presence of a strong base to give novel intermediates which are subsequently reacted in step 2 with tertiary amines, pyridines, tertiary phosphines, sulfides, thiourea etc. to give the onium surfactants.

Novel onium surfactants

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. In step 1, various nonionic surfactants are reacted with certain chloromethylated aromatics in the presence of a strong base to give novel intermediates which are subsequently reacted in step 2 with tertiary amines, pyridines, tertiary phosphines, sulfides, thiourea etc. to give the onium surfactants.

A method for electrodeposition of an organic material on an electroconductive surface comprising placing the electroconductive surface to be coated in contact with an aqueous dispersion containing a water-insoluble, essentially electrically nonconductive, film-forming, organic polymer as cation-active particles wherein the cation-activity is provided at least predominantly by reducible nitrogen-containing cations and passing an electric current from an electrode through the latex to the electroconductive surface in such a direction that the electroconductive surface is negatively charged, i.e., becomes a cathode in an electrophoretic cell. By use of alternating current, both electrodes become coated with an adherent coating of polymer.

Cathodic electrodeposition of polymers onto a conductive surface

A method for electrodeposition of an organic material on an electroconductive surface comprising placing the electroconductive surface to be coated in contact with an aqueous dispersion containing a water-insoluble, essentially electrically non-conductive, film-forming, organic polymer as cation-active particles wherein the cation-activity is provided at least predominantly by sulfonium cations and passing an electric current from an electrode through the latex to the electroconductive surface in such a direction that the electroconductive surface is negatively charged, i.e., becomes a cathode in an electrophoretic cell. By use of alternating current both electrodes become coated with the polymer.

Cationic deposition of polymers onto a conductive surface

Certain pyridinium surfactants

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 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.+ is a quaternized atom of nitrogen or phosphorus or a tertiary atom of sulfur; A.sup.- 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. In step 1, various nonionic surfactants are reacted with certain chloromethylated aromatics in the presence of a strong base to give novel intermediates which are subsequently reacted in step 2 with tertiary amines, pyridines, tertiary phosphines, sulfides, thiourea etc. to give the onium surfactants.

Structured-particle latexes are prepared from nonionic or slightly cationic latexes, either preformed or polymerized in situ, by emulsion polymerizing monomeric materials which include an ethylenically unsaturated, activated-halogen monomer such as vinylbenzyl chloride in the absence of a sufficient amount of a surfactant to initiate new particles whereby the activated-halogen monomer is copolymerized on the surface of the existing particles which are dispersed in an aqueous media. The resulting structured-particle latex may then be reacted with a nucleophile such as dimethyl sulfide or trimethyl amine to form a latex having stabilizing 'onium' groups such as sulfonium groups or quaternary ammonium groups chemically bound at or near the surface of the polymer particles which are dispersed in aqueous media. The cationic latexes are suitable for coatings and organic pigments.

Cationic structured-particle latexes

A method for electrodeposition of an adherent, water-resistant, cross-linked, organic coating on an electroconductive surface comprising (a) placing the elecroconductive surface to be coated in contact with an aqueous dispersion containing a water-insoluble, essentially electrically non-conductive, film-forming, organic polymer as cation-active, structured particles wherein a substantial portion of the cation-activity is provided by pH independent cationic groups which are chemically bound to the polymer at or near the particle surface and (b) passing an electric current from an electrode through the latex to the electroconductive surface in such a direction that the electroconductive surface is negatively charged, i.e., becomes a cathode in an electrophoretic cell. By use of alternating current both electrodes become coated with an adherent coating of polymer.

Process for electrodeposition of cross-linked polymer coatings

Structured-particle latexes are prepared from nonionic or slightly cationic latexes, either preformed or polymerized in situ, by emulsion polymerizing monomeric materials which include an ethylenically unsaturated, activated-halogen monomer such as vinylbenzyl chloride in the absence of a sufficient amount of a surfactant to initiate new particles whereby the activated-halogen monomer is copolymerized on the surface of the existing particles which are dispersed in aqueous media. To the resulting structured particle latex may then be added conventional cationic surfactants to provide greater stability. The cationic latexes are suitable for coatings.

Structured-particle latexes

An aqueous dispersion containing a water-insoluble, essentially electrically non-conductive, organic polymer as cation-active particles wherein a substantial portion of the cation-activity is provided by isothiouronium cations may be obtained by various methods including emulsion polymerization of hydrophobic monomers using an isothiouronium surfactant or by emulsion copolymerization of a monomer containing isothiouronium groups with hydrophobic monomers.

Isothiouronium stabilized latexes

A method for electrodeposition of an organic material on an electroconductive surface comprising placing the electroconductive surface to be coated in contact with an aqueous dispersion containing a water-insoluble, essentially electrically non-conductive, film-forming, organic polymer as cation-active particles wherein a substantial portion of the cation-activity is provided by sulfoxonium cations and passing an electric current from an electrode through the latex to the electroconductive surface in such a direction that the electroconductive surface is negatively charged, i.e., becomes a cathode in an electrophoretic cell. By use of alternating current both electrodes become coated with an adherent coating of polymer.

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Concord, CA, United States of America

Earl H Wagener