US3328243A - Brominated phenyl thiocyanate composition and wood treatment method - Google Patents

Brominated phenyl thiocyanate composition and wood treatment method Download PDF

Info

Publication number
US3328243A
US3328243A US505954A US50595465A US3328243A US 3328243 A US3328243 A US 3328243A US 505954 A US505954 A US 505954A US 50595465 A US50595465 A US 50595465A US 3328243 A US3328243 A US 3328243A
Authority
US
United States
Prior art keywords
wood
thiocyanate
composition
brominated phenyl
phenyl thiocyanate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US505954A
Inventor
Paul A Wolf
Francis J Bobalek
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dow Chemical Co
Original Assignee
Dow Chemical Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dow Chemical Co filed Critical Dow Chemical Co
Priority to US505954A priority Critical patent/US3328243A/en
Application granted granted Critical
Publication of US3328243A publication Critical patent/US3328243A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
    • B27K3/34—Organic impregnating agents
    • B27K3/38—Aromatic compounds
    • B27K3/42—Aromatic compounds nitrated, or nitrated and halogenated
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/48—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —S—C≡N groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
    • B27K3/34—Organic impregnating agents
    • B27K3/44—Tar; Mineral oil

Definitions

  • the present invention is concerned with wood treatment and is directed to methods employing and compositions comprising a brominated phenyl thiocyanate of the formula for wood treatment.
  • R represents an alkyl radical being of from 1 to 4, both inclusive, carbon atoms.
  • brominated phenyl thiocyanate is used to refer only to one or more materials of the foregoing definition.
  • the products to be employed in accordance with the present invention are odorless and typically are crystalline solid materials.
  • Representative products include the following: (3-bromo-4-hydroxy-5-methylphenyl) thiocyanate; (3-bromo-4-hydroxy-S-ethylphenyl) thiocyanate; (3-bromo-4-hydroxy-5-isopropylphenyl) thiocyanate; (3- bromo-4-hydroxy-4-n-buty1phenyl) thiocyanate; and (3- bromo-4-hydroxy-5-tert.-butylphenyl) thiocyanate.
  • the practice of the present invention affords excellent protection of woodfrom attack by microbial organisms, in particular, from attack by lower plant organisms, such as those organisms causing mildew.
  • the present brominated phenyl thiocyanates afford such protection over an extended period of time following treatment.
  • the method of the present invention comprises the step of treating wood with an antimicrobial amount of brominated phenyl thiocyanate. It is critical that the practice of the present invention results in the treatment of wood with an antimicrobial amount of active agent. However, the precise amount of brominated phenyl thiocyanate to be employed varies with factors such as the mode of treatment, the extent of protection desired, the kind of wood, and the like. In general, good results are obtained when employing brominated phenyl thiocyanate in an amount suflicient to produce a concentration in the wood of at least about 0.04 pound of brominated phenyl thiocyanate per cubic foot of wood.
  • brominated phenyl thiocyanate employed is dictated by the capacity of the wood to absorb and retain the active agent, and, in addition, the use of higher amounts, such as amounts in substantial excess of about 0.2 pound per cubic foot, is not always economical, since it does not in all instances result in a correspondingly higher level of protection.
  • the method of the present invention is carried out by treating wood, typically otherwise untreated, with a composition comprising brominated phenyl thiocyanate and solvent.
  • solvents include the aromatic hydrocarbon solvents, such as benzene, toluene, xylene, and naphthalene; various petroleum derivative products, such as kerosene, mineral spirits, and the like; and the materials generally designated "ice as creosote, which materials are derived from coal tar or wood tar and which themselves exhibit wood-preserving properties: such materials include coal tar creosote, coke oven tar creosote, water gas tar creosote, petroleum oil creosote, wood creosote, mixtures thereof and the like.
  • aromatic hydrocarbon solvents such as benzene, toluene, xylene, and naphthalene
  • various petroleum derivative products such as kerosene, mineral spirits, and the like
  • materials generally designated "ice as creosote which materials are derived from coal tar or wood tar and which themselves exhibit wood-preserving properties: such materials include coal tar creosote,
  • the method of the present invention is carried out by the treatment of wood with greases, oils, and the like.
  • typical compositions are modified by the incorporation therein of brominated phenyl thiocyanate in an amount sufiicient to provide an antimicrobial concentration in the wood.
  • Typical compositions include those comprising an aromatic petroleum oil gel, a term which designates a composition of the general physical consistency of cup grease and consisting essentially of a normally fluid highly aromatic petroleum product or oil in association with sufiicient of a gelatin agent to exhibit, under normal conditions of temperature, the properties of cup grease as regards viscosity and consistency.
  • Typical compositions also include those liquids, frequently wood-preserving liquids such as creosote, which are thickened with a thickening agent to yield a grease-like composition. Numerous other typical compositions are known. The present brominated phenyl thiocyanate is incorporated therein, ordinarily by simple addition.
  • the practice of the present invention can be carried out by simple application to wood, as with brush, sprays, rollers, and the like.
  • a composition comprising active agent and solvent
  • the solvent be as nearly completely volatile as possible, to avoid so-called bleeding upon subsequent painting.
  • the holdof wood thus treated for several days prior to painting facilitates solvent evaporation.
  • employing this embodiment is to serve as the sole protection for the wood, especially when the wood so treated is to be exposed to especially harsh conditions, even better protection is desirable and can be obtained when the application is carried out under special conditions of temperature and pressure.
  • the wood which is to be treated is placed in a vessel from which the contained atmosphere is evacuated to achieve a subatmospheric pressure, such as from 5 to about 600 millimeters mercury. Thereafter a composition comprising brominated phenyl thiocyanate and solvent is introduced into the vessel so as to effect the immersion of the wood therein.
  • this mixture is at an elevated temperature, for example, from 180 to 200 F.
  • the contents of the vessel can thereafter be placed successively under superatmospheric pressure, such as from about 1.5 to about atmospheres, in some instances more, and under subatmospheric pressure, as previously set forth, for periods of time to facilitate the impregnation of the solution into the wood.
  • Techniques for facilitating penetration of the solution into the wood such as incision, debarking, or other preparation of the wood, can be utilized.
  • the amount of brominated phenyl thiocyanate present will depend upon such factors as whether the composition is to be employed as a concentrate or as an ultimate treating composition, and in the instance of the latter, other factors such as the degree of protection desired and the type of wood.
  • the brominated phenyl thiocyanate can be present in an amount of from 0.5 to 99.5 percent, and the solvent can be present in an amount of from 0.5 to 99.5 percent, the percentages being based on the weight of ultimate composition.
  • the brominated phenyl thiocyanate in a grease-type composition, can be present in an amount of from 0.5 to 99.5 percent of total composition.
  • the brominated phenyl thiocyanate can be present in an amount of from 0.5 to 99.5 percent of total composition.
  • it can be diluted with additional solvent or with other woodtreating materials to obtain the ultimate treating composition.
  • a composition of active agent and solvent, or agrease or oil composition comprising the active agent can also include other materials typically employed in Wood treatment, such as drying materials; water repellants; binding materials, frequently of a synthetic polymeric nature; and the like.
  • the composition can also comprise other preservative materials.
  • Example 1 A wood treating composition is prepared by dispersing (3-bromo-4-hydroxy-5-methylphenyl) thiocyanate in mineral spirits with a commercial product identified simply as a water repellant. The dispersion is carried out with such amounts that three modified compositions are pre pared. The three compositions have the following formulations:
  • compositions are adapted to be employed for wood treatment, especially prior to subsequent painting.
  • Example 2 The compositions of Example 1 are employed for wood treatment prior to painting with a commercial alkyd paint formulation. In these procedures, the modified compositions of Example 1 are applied with a brush to separate panels of Southern yellow pine. The panels are then permitted to stand for approximately two weeks, to assure evaporation of the mineral spirits. Following this period, the panels are painted with the commercial alkyd paint formulation, which is described as being of the following composition:
  • the alkyd paint formulation is specifically lacking any antimicrobial agent.
  • Other panels are treated with a composition consisting of 33.3 percent water repellant and 66.7 percent mineral spirits and thereafter painted with the commercial alkyd paint formulation to serve as a control. After painting, all panels are permitted to dry and then placed outdoors in a subtropical climate of generally high temperatures and humidity. The panels are placed in a northerly exposure in a nearly vertical position, so as to be advantageous to fungal development, in particular, mildew development. The outdoor placement of the panels is made at the beginning of the summer season, and observation of the panels is conducted recurringly throughout the season.
  • Example 3 The procedures of Example 2 are duplicated except that in the three treating compositions applied prior to painting, the brominated phenyl thiocyanate employed is (3- bromo-4-hydroxy-5-isopropylphenyl) thiocyanate. Results similar to those set forth in Example 2 are obtained.
  • Example 4 The evaluation procedures of Example 2 are duplicated except that instead of the alkyd paint formulation, there is employed a basic latex paint formulation.
  • the formulation is as follows:
  • Example 5 The procedures of Example 4 are duplicated except that in the three treating compositions applied prior to painting, the brominated phenyl thiocyanate employed is (3-bromo-4-hydroxy-5-tert.-butylphenyl) thiocyanate. Results essentially the same as those set forth in Example 4 are obtained:
  • the brominated phenyl thiocyanate compounds to be employed in accordance with the present invention are prepared by reacting a phenol compound of the formula with sodium thiocyanate in methanol saturated with sodium bromide. Thereafter, a solution of bromine in methanol saturated with sodium bromide is added portionwise over a period of time. Separation and, if desired, purification, are conducted in conventional manners.
  • Method which comprises the step of treating wood with an antimicrobial amount of brominated phenyl thiocyanate of the formula wherein R represents an alkyl radical of from 1 to 4 carbon atoms.
  • Composition which comprises brominated phenyl thiocyanate of the formula Br- R I SCN wherein R represents an alkyl radical of from 1 to 4 carbon atoms and a solvent for said brominated phenyl thiocyanate.
  • composition of claim 9 in which the brominated phenyl thiocyanate is (3-bromo-4-hydroxy-S-methylphenyl) thiocyanate.
  • composition of claim 9 in which the brominated phenyl thiocyanate is (3-bromo-4-hydroxy-5-isopropylphenyl) thiocyanate.

Description

United States Patent 3,328,243 BROMHNATED PHENYL THIOCYANATE COMPQ- SITIGN AND WOOD TREATMENT METHOD Paul A. Wolf and Francis J. Bobalek, Midland, Mich, assignors to The Dow Chemical Company, Midland, Mich, a corporation of Delaware No Drawing. Filed Nov. 1, 1965, Ser. No. 505,954 13 Claims. (Cl. 167-38.6)
The present invention is concerned with wood treatment and is directed to methods employing and compositions comprising a brominated phenyl thiocyanate of the formula for wood treatment. In the above and succeeding formula, R represents an alkyl radical being of from 1 to 4, both inclusive, carbon atoms. In the present specification and claims, the term brominated phenyl thiocyanate is used to refer only to one or more materials of the foregoing definition. The products to be employed in accordance with the present invention are odorless and typically are crystalline solid materials. Representative products include the following: (3-bromo-4-hydroxy-5-methylphenyl) thiocyanate; (3-bromo-4-hydroxy-S-ethylphenyl) thiocyanate; (3-bromo-4-hydroxy-5-isopropylphenyl) thiocyanate; (3- bromo-4-hydroxy-4-n-buty1phenyl) thiocyanate; and (3- bromo-4-hydroxy-5-tert.-butylphenyl) thiocyanate.
The practice of the present invention affords excellent protection of woodfrom attack by microbial organisms, in particular, from attack by lower plant organisms, such as those organisms causing mildew. Moreover, the present brominated phenyl thiocyanates afford such protection over an extended period of time following treatment.
The method of the present invention comprises the step of treating wood with an antimicrobial amount of brominated phenyl thiocyanate. It is critical that the practice of the present invention results in the treatment of wood with an antimicrobial amount of active agent. However, the precise amount of brominated phenyl thiocyanate to be employed varies with factors such as the mode of treatment, the extent of protection desired, the kind of wood, and the like. In general, good results are obtained when employing brominated phenyl thiocyanate in an amount suflicient to produce a concentration in the wood of at least about 0.04 pound of brominated phenyl thiocyanate per cubic foot of wood. The upper limit as to amount of brominated phenyl thiocyanate employed is dictated by the capacity of the wood to absorb and retain the active agent, and, in addition, the use of higher amounts, such as amounts in substantial excess of about 0.2 pound per cubic foot, is not always economical, since it does not in all instances result in a correspondingly higher level of protection.
In a preferred embodiment, the method of the present invention is carried out by treating wood, typically otherwise untreated, with a composition comprising brominated phenyl thiocyanate and solvent.
The identity of the solvent is not critical, it being necessary only that the rominated phenyl thiocyanate be sufficiently soluble therein that it serves to carry the active agent into the wood in an antimicrobial amount. Preferred solvents include the aromatic hydrocarbon solvents, such as benzene, toluene, xylene, and naphthalene; various petroleum derivative products, such as kerosene, mineral spirits, and the like; and the materials generally designated "ice as creosote, which materials are derived from coal tar or wood tar and which themselves exhibit wood-preserving properties: such materials include coal tar creosote, coke oven tar creosote, water gas tar creosote, petroleum oil creosote, wood creosote, mixtures thereof and the like.
In another embodiment, the method of the present invention is carried out by the treatment of wood with greases, oils, and the like. In this embodiment, typical compositions are modified by the incorporation therein of brominated phenyl thiocyanate in an amount sufiicient to provide an antimicrobial concentration in the wood. Typical compositions include those comprising an aromatic petroleum oil gel, a term which designates a composition of the general physical consistency of cup grease and consisting essentially of a normally fluid highly aromatic petroleum product or oil in association with sufiicient of a gelatin agent to exhibit, under normal conditions of temperature, the properties of cup grease as regards viscosity and consistency. Typical compositions also include those liquids, frequently wood-preserving liquids such as creosote, which are thickened with a thickening agent to yield a grease-like composition. Numerous other typical compositions are known. The present brominated phenyl thiocyanate is incorporated therein, ordinarily by simple addition.
The practice of the present invention can be carried out by simple application to wood, as with brush, sprays, rollers, and the like. When the practice of the present invention is carried out as a pretreatment prior to subsequent painting, such application of a composition comprising active agent and solvent is usually adequate and preferred. In such instance, it is preferred that the solvent be as nearly completely volatile as possible, to avoid so-called bleeding upon subsequent painting. The holdof wood thus treated for several days prior to painting facilitates solvent evaporation. However when the practice of the present invention, employing this embodiment, is to serve as the sole protection for the wood, especially when the wood so treated is to be exposed to especially harsh conditions, even better protection is desirable and can be obtained when the application is carried out under special conditions of temperature and pressure. In general, better penetration is obtained when a solvent composition of brominated phenyl thiocyanate is at elevated temperatures and when the Wood to be treated is in a chamber at subatmospheric pressure. The best results are obtained with procedures combining both conditions, which procedures are generally spoken of as wood impregnation.
In general, when employing the impregnation procedures, the wood which is to be treated is placed in a vessel from which the contained atmosphere is evacuated to achieve a subatmospheric pressure, such as from 5 to about 600 millimeters mercury. Thereafter a composition comprising brominated phenyl thiocyanate and solvent is introduced into the vessel so as to effect the immersion of the wood therein. Preferably this mixture is at an elevated temperature, for example, from 180 to 200 F. The contents of the vessel can thereafter be placed successively under superatmospheric pressure, such as from about 1.5 to about atmospheres, in some instances more, and under subatmospheric pressure, as previously set forth, for periods of time to facilitate the impregnation of the solution into the wood. Techniques for facilitating penetration of the solution into the wood, such as incision, debarking, or other preparation of the wood, can be utilized.
In the compositions to be employed in accordance with the present invention, the amount of brominated phenyl thiocyanate present will depend upon such factors as whether the composition is to be employed as a concentrate or as an ultimate treating composition, and in the instance of the latter, other factors such as the degree of protection desired and the type of wood. In a composition comprising brominated phenyl thiocyanate and solvent, the brominated phenyl thiocyanate can be present in an amount of from 0.5 to 99.5 percent, and the solvent can be present in an amount of from 0.5 to 99.5 percent, the percentages being based on the weight of ultimate composition. Similarly, in a grease-type composition, the brominated phenyl thiocyanate can be present in an amount of from 0.5 to 99.5 percent of total composition. When such composition is employed as a concentrate, it can be diluted with additional solvent or with other woodtreating materials to obtain the ultimate treating composition.
When the practice of the present invention is to be employed for pretreatment of wood prior to painting, good results are generally obtained when utilizing a composition comprising solvent and from about 0.5 to percent of active agent by weight of ultimate composition; this composition is then applied at the rate of about 3 or more gallons per 1,000 square foot of wood surface.
A composition of active agent and solvent, or agrease or oil composition comprising the active agent, can also include other materials typically employed in Wood treatment, such as drying materials; water repellants; binding materials, frequently of a synthetic polymeric nature; and the like. The composition can also comprise other preservative materials.
The following examples illustrate the present invention and will enable those skilled in the art to practice the invention.
Example 1 A wood treating composition is prepared by dispersing (3-bromo-4-hydroxy-5-methylphenyl) thiocyanate in mineral spirits with a commercial product identified simply as a water repellant. The dispersion is carried out with such amounts that three modified compositions are pre pared. The three compositions have the following formulations:
All percentages are based on weight of the ultimate composition. These compositions are adapted to be employed for wood treatment, especially prior to subsequent painting.
Example 2 The compositions of Example 1 are employed for wood treatment prior to painting with a commercial alkyd paint formulation. In these procedures, the modified compositions of Example 1 are applied with a brush to separate panels of Southern yellow pine. The panels are then permitted to stand for approximately two weeks, to assure evaporation of the mineral spirits. Following this period, the panels are painted with the commercial alkyd paint formulation, which is described as being of the following composition:
Pounds per 100 gallons Titanium dioxide 300 Talc 315 Long oil alkyl, 80% solid 350 Drier:
Lead naphthenate (24% metal) 6.9
Manganese naphthenate (6% metal) 1.4
Heavy mineral spirits 221.0
In particular, the alkyd paint formulation is specifically lacking any antimicrobial agent. Other panels are treated with a composition consisting of 33.3 percent water repellant and 66.7 percent mineral spirits and thereafter painted with the commercial alkyd paint formulation to serve as a control. After painting, all panels are permitted to dry and then placed outdoors in a subtropical climate of generally high temperatures and humidity. The panels are placed in a northerly exposure in a nearly vertical position, so as to be advantageous to fungal development, in particular, mildew development. The outdoor placement of the panels is made at the beginning of the summer season, and observation of the panels is conducted recurringly throughout the season.
The results of the observations are set forth in the following table:
TABLE I Months of mildewfree exposure Control panels 2 Panels treated with (3-bromo-4-hydroxy-5-methyl phenyl) thiocyanate:
0.5 percent 34 1.0 percent 57 2.0 percent 5-7 Example 3 The procedures of Example 2 are duplicated except that in the three treating compositions applied prior to painting, the brominated phenyl thiocyanate employed is (3- bromo-4-hydroxy-5-isopropylphenyl) thiocyanate. Results similar to those set forth in Example 2 are obtained.
Example 4 The evaluation procedures of Example 2 are duplicated except that instead of the alkyd paint formulation, there is employed a basic latex paint formulation. The formulation is as follows:
Pounds per gallons Water 255.10 Ethylene glycol 15.0 Dispersant 2.0 Antifoamer 2.0 Viscosity controlling agent 4.0 Titanium dioxide 230.0 Extenders 185.0 Latex (aqueous emulsion of polyacrylate) 453.0 Defoamer 5.0
The results of the observations are set forth in the following table:
TABLE II Months of mildewfree exposure Control panels 2 Panels treated with (3-bromo-4-hydroxy-5-methylphenyl) thiocyanate:
0.5 percent 5-7 1.0 percent 5-7 2.0 percent 7 Example 5 The procedures of Example 4 are duplicated except that in the three treating compositions applied prior to painting, the brominated phenyl thiocyanate employed is (3-bromo-4-hydroxy-5-tert.-butylphenyl) thiocyanate. Results essentially the same as those set forth in Example 4 are obtained:
The brominated phenyl thiocyanate compounds to be employed in accordance with the present invention are prepared by reacting a phenol compound of the formula with sodium thiocyanate in methanol saturated with sodium bromide. Thereafter, a solution of bromine in methanol saturated with sodium bromide is added portionwise over a period of time. Separation and, if desired, purification, are conducted in conventional manners.
We claim:
1. Method which comprises the step of treating wood with an antimicrobial amount of brominated phenyl thiocyanate of the formula wherein R represents an alkyl radical of from 1 to 4 carbon atoms.
2. Method of claim 1 wherein the brominated phenyl thiocyanate is (3-bromo-4-hydroxy-5-methylphenyl) thiocyannate.
3. Method of claim 1 wherein the brominated phenyl thiocyanate is (3-bromo-4-hydroxy-5 -isopropylphenyl) thiocyanate.
4. Method of claim 1 wherein the step of treating wood is carried out with a composition comprising the brominated phenyl thiocyanate and a solvent.
5. Method of claim 4 wherein the solvent is mineral spirits.
6. Method of claim 4 wherein the solvent is creosote.
7. Method of claim 4 wherein the brominated phenyl thiocyanate is (3-bromo-4-hydroxy-5-methylphenyl) thiocyanate.
8. Method of claim 4 wherein the brominated phenyl thiocyanate is (3-bromo-4-hydroxy-5-isopropylpheny1) thiocyanate.
9. Composition which comprises brominated phenyl thiocyanate of the formula Br- R I SCN wherein R represents an alkyl radical of from 1 to 4 carbon atoms and a solvent for said brominated phenyl thiocyanate.
10. Composition of claim 9 in which the brominated phenyl thiocyanate is (3-bromo-4-hydroxy-S-methylphenyl) thiocyanate.
11. Composition of claim 9 in which the brominated phenyl thiocyanate is (3-bromo-4-hydroxy-5-isopropylphenyl) thiocyanate.
12. Composition of claim 9 in which the solvent is mineral spirits.
13. Composition of claim 9 in which the solvent is creosote.
No reference cited.
ALBERT T. MEYERS, Primary Examiner.
DALE R. MAHANAND, Assistant Examiner.

Claims (1)

1. METHOD WHICH COMPRISES THE STEP OF TREATING WOOD WITH AN ANTIMICROBIAL AMOUNT OF BROMINATED PHENYL THIOCYANATE OF THE FORMULA
US505954A 1965-11-01 1965-11-01 Brominated phenyl thiocyanate composition and wood treatment method Expired - Lifetime US3328243A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US505954A US3328243A (en) 1965-11-01 1965-11-01 Brominated phenyl thiocyanate composition and wood treatment method

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US505954A US3328243A (en) 1965-11-01 1965-11-01 Brominated phenyl thiocyanate composition and wood treatment method

Publications (1)

Publication Number Publication Date
US3328243A true US3328243A (en) 1967-06-27

Family

ID=24012565

Family Applications (1)

Application Number Title Priority Date Filing Date
US505954A Expired - Lifetime US3328243A (en) 1965-11-01 1965-11-01 Brominated phenyl thiocyanate composition and wood treatment method

Country Status (1)

Country Link
US (1) US3328243A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3377175A (en) * 1965-11-01 1968-04-09 Dow Chemical Co Preservation of coatings
US3389163A (en) * 1965-10-18 1968-06-18 Consolidation Coal Co 2-bromo-4-thiocyano-6-isopropylphenol
US3389162A (en) * 1965-10-18 1968-06-18 Consolidation Coal Co 6-bromo-4-thiocyano-omicron-cresol

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3389163A (en) * 1965-10-18 1968-06-18 Consolidation Coal Co 2-bromo-4-thiocyano-6-isopropylphenol
US3389162A (en) * 1965-10-18 1968-06-18 Consolidation Coal Co 6-bromo-4-thiocyano-omicron-cresol
US3377175A (en) * 1965-11-01 1968-04-09 Dow Chemical Co Preservation of coatings

Similar Documents

Publication Publication Date Title
EP0149625B1 (en) Preservative composition
US4612255A (en) Water dispersible compositions for preparing aqueous water repellent systems, aqueous water repellent systems, and process for treatment of permeable substrates therewith
JP2900040B2 (en) Biocides to protect industrial materials and water systems
MXPA94006411A (en) Oxatiazinas conservadoras de mad
US4508568A (en) Biocidal wood preservative composition and method
US4337093A (en) Wood preserving composition and method of using same
US3328243A (en) Brominated phenyl thiocyanate composition and wood treatment method
GB1564188A (en) Preservative for wood and wood-based materials
US2015739A (en) Wax coating composition
US2209970A (en) Wood preservation
US3049471A (en) Preservative composition
PT835054E (en) EMULSIONED COMPOSITIONS OF 1,4-BIS (BROMOACETOXY) -2-BUTENE UTIS AS MICROBICIDE AND CONSERVANE
EP0147976A1 (en) Biocidal amine salts
US2904467A (en) Wood preservative grease
NO154298B (en) Means for the preservation of wood and wood materials.
JPH06504960A (en) Antibacterial composition containing alkyl sulfosuccinate salt and oil component
US3764378A (en) Wood treated with a preservative composition
US3266981A (en) Biologically toxic compositions containing boron-phenol complexes and methods
US3702784A (en) Preservative compositions
FI73693B (en) TRIORGANOTENN-ACETYLSALICYLAT OCH DESSA INNEHAOLLANDE BIOCIDA AEMNEN.
US4968455A (en) Tris(triorganotin) esters of trimeric fatty acids
US4051279A (en) Protective coatings
US4684663A (en) Biocidal tributyltin compounds
US2041130A (en) Toxic antifouling material
US3081221A (en) Phenolic antimicrobial compositions containing a polyamine-salicylal-dehyde condensation product