Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/22—Tin compounds
  • C07F7/2224—Compounds having one or more tin-oxygen linkages

Definitions

• This invention relates to novel bioeidal compounds and to their use in the control of the growth of fungi, bacteria, and other microorganisms. More particularly, it relates to organotin salts of monoalkyl alkenylsuccinates and to surface-coating compositions containing these compounds that have improved resistance to deterioration resulting from attack by microorganisms.
• paints and varnishes often have inadequate resistance to the action of micro organisms.
• Some of these coating compositions such as enamels and house paints, contain as their resinous binders drying oils, oleoresinous varnishes, or alkyd resins, which are subject to attack by fungi and bacteria.
• Others for example, aqueous dispersions of water-insolube synthetic linear polymers, generally contain as plasticizers and thickeners materials that have their origin in animal or vegetable sources and that render the compositions susceptible to mildew. The resulting deterioration of the surface-coating compositions seriously hinders their full scale utilization, particularly in those areas and in those applications that are conducive to such attack.
• biocidal materials have been suggested for use in surface-coating compositions, but none have been suggested for use in surface-coating compositions, but none has proven entirely satisfactory in this application. Some do not provide the required prolonged protection against attack by microorganisms, While others undergo sulfide staining and still others hydrolyze in alkaline aqueous paint systems or separate from the applied coating by migration, volatilization, or leaching once the coating has been spread in a thin layer over the surface to be protected.
• This invention relates to biocides that are of particular value in surface-coating compositions.
• biocides which are thoroughly compatible with the resinous binders that commonly are used in surface-coating compositions and which are resistant to sulfide staining, provide excellent and prolonged resistance to deterioration resulting from attack by fungi and other microorganisms without adversely affecting the color, pH, viscosity, and other physical properties of the surface-coating compositions.
• the bioeidal compounds of this invention are organotin salts of monoalkyl alkenylsuccinates. These compounds may be represented by the structural formula wherein each R represents phenyl or an alkyl group having from 4 to 12 carbon atoms; one R represents a straight-chain or branched-chain alkenyl group having from 8 to 22 carbon atoms; the other R' represents hydrogen; and R" represents an alkyl group having from 1 to 16 carbon atoms. Illustrative of these compounds are the following:
• a single organotin salt of a monoalkyl alkenylsuccinate or a mixture of two or more of these compounds may be present in the surface-coating compositions of this invention. Particularly advantageous results have been obtained using tri-n-butyltin salts of monoalkyl alkenylsuccinates.
• organotin compounds of this invention can also be used as agricultural fungicides because they can be applied to plants, to plant seeds, or to the soil in which plants are growing to control the growth of a number of plant pathogens.
• organotin salts of monoalkyl alkenylsuccinates may be prepared by any suitable and convenient procedure. F or example, they may be prepared by the reaction of a trialkyltin oxide with the appropriate monoalkyl ester of an alkenylsuccinic acid.
• organotin compounds of this invention can be used to impart fungal and bacterial resistance to a wide variety of surface-coating compositions including both organic solvent-based and water-based coating systems. They are particularly valuable as biocides in water-based coatings that contain as their resinous binder a water-insoluble synthetic linear addition polymer.
• the novel organotin compounds are used in aqueous dispersions that contain about 10 percent to 60 percent by Weight of a water-insoluble resinous binder that is an oleoresinous hinder or a synthetic linear addition binder.
• Suitable oleoresinous binders include drying oils, such as linseed oil, tung oil, soybean oil, dehydrated castor oil, safllower oil, or fish oil; bodied drying oils; blends of drying oils or bodied drying oils with a resin component, such as limed rosin, an ester gum, or a phenolic resin; oleoresinous varnishes formed by heating one of the afore-mentioned resins with one or more drying oils or bodied drying oils; and alkyd resins, which are resinous products resulting from the reaction of a polyhydric alcohol, such as pentaerythritol or glycerol, with a dicarboylic acid, such as phthalic anhydride, and fatty acids.
• a polyhydric alcohol such as pentaerythritol or glycerol
• the useful aqueous dispersions of synthetic linear addition polymers are ordinarily prepared by the emulsion polymerization of ethylenically unsaturated compounds, especially those of monoethylenically unsaturated character, although butadiene, chlorobutadiene, and isoprene may be used to some extent.
• Illustrative of the synthetic linear addition polymers that can be used as the resinous binder in the aqueous dispersions are polyvinyl acetate; polyvinyl butyrate; polyvinyl chloride; copolymers of vinyl acetate with vinyl chloride; copolymers of vinyl acetate with acrylonitrile; copolymers of vinyl chloride with acrylonitrile; copolymers of vinyl chloride with vinylidene chloride; polyethylene; polyisobutylene; polystyrene; copolymers of styrene with butadiene; copolymers of acrylonitrile with butadiene; copolymers of methacrylic acids esters of alcohols having 1 to 8 carbon atoms with vinyl acetate; vinyl chloride, acrylonitrile, or styrene; copolymers of acrylic acid esters of alcohols having 1 to 8 carbon atoms with vinyl acetate, vinyl chloride, acrylonitrile, or styren
• an organotin salt of a monoalkyl alkenylsuccinate is used as the biocide in a solvent-based system that contains an oleoresinous binder as hereinbefore defined.
• organotin compound Only a small concentration of the organotin compound need be present in the surface-coating compositions of this invention. It has been found that as little as 0.10 percent of one or more of these compounds, based on the weight of the composition, will bring about an appreciable improvement in the resistance of the composition to attack by microorganisms. Three percent or more of the biocidal compounds can be used, but these larger amounts generally do not provide further improvement in the properties of the surface-coating compositions and for this reason are not ordinarily used.
• biocidal compound that will provide optimum protection for a surface-coating composition depends upon such factors as the choice of biocidal compound, the choice of resinous binder and other components of the surfacecoating composition and the amount of each that is used, and the application for which the coating composition is intended, in most cases about 1 percent to 2 percent of theorganotin compound, based on the weight of the surface-coating composition, is used.
• the surface-coating compositions of this invention may contain various auxiliary materials, such as pigments, extenders, solvents, dyes, deforming agents, driers, emulsifiers, plasticizers, and the like in the amounts ordinarily used for these purposes.
• the organotin compound that is used as the biocide may be incorporated into the surface-coating composition by any convenient procedure. For example, it can be combined with the pigments and other components to form a pigment phase that is mixed with the resinous binder and water or organic solvent to form the surface-coating composition. Alternatively, it can be added to a composition that contains the resinous binder, pigment, and water or organic solvent.
• the organotin compound can be added as such to the other components, or it can be added as a solution of the organotin compound in, for example, an alcohol, ether, or ketone.
• EXAMPLE 1 A mixture of 13.3 grams (0.050 mole) of dodecenylsuccinic anhydride and 4.0 grams (0.054 mole) of n-butyl alcohol was heated with stirring at 100 C. for one hour. It was then heated to 100 C. under vacuum (15 mm.) for one hour. Fifteen grams of bis-(tri-n-butyltin)-oxide was added to the half ester at 50 C., and the reaction mixture was heated with stirring at 1l0120 C. for two hours. The tri-n-butyltin salt of mono-n-butyldodecenylsuccinate obtained was a pale yellow oil that contained 18.5% Sn (calculated, 18.8% Sn). Its structure was confirmed by infrared analysis.
• organotin compounds of this invention are effective biocides for paint systems, and'particularly for acrylic and polyvinyl acetate paint systems. They impart to the paints alkaline conditions and loses its effectiveness on aging in acrylic paint systems and other alkaline paint systems.
• each R represents phenyl or an alkyl group having from 4 to 12 carbon atoms; one R represents an alkenyl group having from 8 to 22 carbon atoms; the other R represents hydrogen; and R" represents an alkyl group having from 1 to 16 carbon atoms.
• each R represents n-butyl. References Clted 3.
• the organotin compound as set forth in claim 1 that UNITED STATES PATENTS is (tri-n-butyltin)-n-buty1-dodccenylsuccinate. 3 019 247 1/1962 M t 1 I e ack et a1. 260-429.7 4.
• 26 9 is (tri-n-butyltin)-methyl-dodecenylsuccinate.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Paints Or Removers (AREA)
• Compositions Of Macromolecular Compounds (AREA)

Applications Claiming Priority (1)

Publications (1)

Family

ID=25347453

Family Applications (1)

Country Status (10)

Cited By (3)

• 0
  • BE BE756476D patent/BE756476A/xx unknown
• 1969
  • 1969-10-14 US US866366A patent/US3651107A/en not_active Expired - Lifetime
• 1970
  • 1970-09-22 ZA ZA706462A patent/ZA706462B/xx unknown
  • 1970-09-24 AU AU20303/70A patent/AU2030370A/en not_active Expired
  • 1970-10-01 DE DE19702048354 patent/DE2048354A1/de active Pending
  • 1970-10-06 NL NL7014661A patent/NL7014661A/xx unknown
  • 1970-10-09 GB GB48098/70A patent/GB1291520A/en not_active Expired
  • 1970-10-13 AT AT922970A patent/AT299243B/de not_active IP Right Cessation
  • 1970-10-13 FR FR7036992A patent/FR2065424A5/fr not_active Expired
  • 1970-10-14 CA CA095,575A patent/CA969967A/en not_active Expired

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