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US 4,064,338 AGranted
Method for preparing biologically active copolymers of triorganotin acrylates
AssigneeM&T Chemicals Inc.
InventorDavid B. Russell
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AssigneeM&T Chemicals Inc.
InventorDavid B. Russell
Estimating the term…
Biologically active copolymers wherein a portion of the repeating units exhibit a triorganotin moiety (R.sub.3 Sn--) are prepared by solution polymerization using liquid aliphatic or cycloaliphatic hydrocarbons as the polymerization medium. The physical and chemical properties of the copolymers make them more suitable for use as biocides than polymers prepared using methods described in the prior art.
In an improved method for preparing biologically active polymers exhibiting reduced rates of hydrolysis and reduced second order glass transition temperatures by reacting at least one solubilized triorganotin compound of the general formula ##STR3## with at least one solubilized monomer of the general formula ##STR4## at a temperature from 50.degree. to 100.degree. C. and in the presence of an organic solvent for the monomers and an effective amount of a free radical polymerization initiator, wherein R.sup.1 represents an alkyl radial containing from 1 to 8 carbon atoms, a cyclohexyl or a phenyl radical, R.sup.2 and R.sup.4 are individually selected from hydrogen and methyl radicals and R.sup.3 represents an alkyl radical containing from 1 to 18 carbon atoms, a cyclohexyl or a phenyl radical, the improvement which consists of reacting said monomers in an organic solvent containing from 50 to 100% by volume of at least one liquid aliphatic or cycloaliphatic hydrocarbon containing from 5 to 16 carbon atoms, any remaining portion of said organic solvent consisting essentially of at least one liquid aromatic hydrocarbon.
Dependencies are inferred from the claim text.
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Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing…:…
Macromolecular compounds: containing tin
Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
Coating compositions
Term ended 20 Dec 1994 (estimated)
USPTO file history isn’t available for this patent, so only indexed dates are shown.
This invention relates to a method for preparing copolymers incorporating a triorganotin moiety. This invention further relates to a method for preparing tin-containing polymers which retain their biological activity over a longer period of time relative to prior art materials.
The biological activity of polymers containing at least one triorganotin moiety (R.sub.3 Sn--) is well known. U.S. Pat. No. 3,167,473 discloses polymers obtained by polymerizing triorganotin derivatives of ethylenically unsaturated acids, including acrylic, methacrylic, and vinylbenzoic acids. The resultant products are employed as the toxicant in antifouling marine coatings and in compositions applied to agricultural food crops for the purpose of protecting them against infestation by a variety of harmful organisms, particularly fungi.
In accordance with the teaching of the aforementioned U.S. Pat. No. 3,167,473 the triorganotin-containing polymers are obtained using conventional bulk, solution or emulsion polymerization techniques. The examples of this patent disclose emulsion and bulk polymerization.
The following examples illustrate the present method and the improved polymers obtained thereby.
This example demonstrates the preparation of a preferred biologically active copolymer. A 3 liter capacity polymerization reactor equipped with a nitrogen inlet, water cooled condenser, thermometer, and mechanically driven stirrer is charged with 375 g. of tributyltin methacrylate, 100 g. of methyl methacrylate, 1 liter of heptane and 0.095 g. of benzoyl peroxide (equivalent to 0.02%, based on total monomer weight). The contents of the reactor were heated at 80.degree. C. for 16 hours to obtain a 95% conversion to polymer.
A number of other copolymers were prepared using the foregoing procedure with the exception that the heptane was replaced by an equal volume of xylene or a mixture containing 0.5 liter of heptane and 0.5 liter of xylene. The latter is within the scope of the present method.