CA3149341C - Synergistic wood preservative composition comprising polymeric betaine and carbamate - Google Patents
Synergistic wood preservative composition comprising polymeric betaine and carbamate Download PDFInfo
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- CA3149341C CA3149341C CA3149341A CA3149341A CA3149341C CA 3149341 C CA3149341 C CA 3149341C CA 3149341 A CA3149341 A CA 3149341A CA 3149341 A CA3149341 A CA 3149341A CA 3149341 C CA3149341 C CA 3149341C
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- 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
- A01N47/08—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 one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
-
- 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
- B27K3/50—Mixtures of different organic impregnating agents
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
-
- 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
- B27K2240/00—Purpose of the treatment
- B27K2240/20—Removing fungi, molds or insects
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Forests & Forestry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
Abstract
A synergistic wood preservation composition comprising a polymeric betaine and 3-iodo-2-propynyl butyl carbamate (IPBC). Also, a method of controlling microorganisms that produce mold and/or sapstain on wood or wood products by applying to a wood or wood product the synergistic wood preservation composition to control the microorganisms.
Description
CA 3,149,341 CPST Ref: 40659/00001 AND
2 CARBAMATE
3
4 CROSS-REFERENCE TO RELATED APPLICATIONS
The present application claims priority to U.S. Patent Application No.
62/884,738, filed August 9, 6 2019, entitled "SYNERGISTIC WOOD PRESERVATIVE COMPOSITION COMPRISING
POLYMERIC
7 BETAINE AND CARBAMATE".
1. Field of the Invention 11 The present invention pertains to synergistic compositions suitable for use in the treatment and 12 preservation of wood and wood products. The antimicrobial compositions of this invention include wood 13 preservative compositions comprising a polymeric betaine and an iodopropynyl compound. These 14 combinations are especially useful in protecting wood and wood products from spoilage resulting from the growth of microorganisms, especially microorganisms that produce mold and sapstain.
16 2. Description of the Background 17 Substrates of all types, when exposed to common environmental conditions, are prone to attack, 18 spoilage and various kinds of destruction by a variety of species of microorganisms including fungi, yeast, 19 bacteria, algae, and mold. As a result, there has always been a great need for effective and economical means to protect various materials, for extended periods of time, from the defacement, deterioration, and 21 destruction caused by such microorganisms. Materials that need protection against such microorganisms 22 include, for example, wood and wood products, which are prone to degradation by the action of 23 objectionable microorganisms. Such degradation may produce, inter alia, deterioration, discoloration, the 24 formation of objectionable odors, and other adverse effects on the substrate.
A great deal of effort has gone into developing a wide variety of materials which, to various 26 degrees, are effective in retarding or preventing the growth of, and accompanying destruction caused by, 27 such microorganisms in a variety of circumstances. Such antimicrobial materials included halogenated 28 compounds, organometallic compounds, quaternary ammonium compounds, phenolics, metallic salts, 29 heterocyclic amines, formaldehyde adducts, organosulfur compounds, and the like.
No single organic antimicrobial compound is able to provide protection against all microorganisms 31 and is suitable for all applications. In addition to such limitations concerning efficacy, other limitations 32 may restrict the usefulness of certain antimicrobials. For example the stability, physical properties, 33 toxicological profile, regulatory considerations, economic considerations or environmental concerns may 34 render a particular ingredient unsuitable for a particular use. There is a need, therefore, to constantly develop new combinations that will offer broad spectrum protection from a variety of needs.
CPST Doc: 415843.2 Date Regue/Date Received 2022-08-04 CA 3,149,341 CPST Ref: 40659/00001 1 A judicious choice of combinations may provide a way to maximize benefits while at the same 2 time minimize problems. Ideally, a combination wherein the antimicrobial activity is enhanced while the 3 less desirable properties are suppressed or reduced can provide a superior product. The task is to find 4 such combinations that will provide protection against a wide variety of problem microorganisms, will not adversely affect the product to be protected, will maintain its integrity for an extended period of time, and 6 will not have any strong adverse effects on health or the environment.
9 The present invention is directed to certain synergistic preservative compositions comprising a polymeric betaine and an iodopropynyl compound. The present invention is also directed to methods for 11 controlling mold and/or sapstain on wood or wood products by application of an effective amount of such 12 compositions to the wood or wood product substrate.
It has been found that when iodopropynyl compounds such as 3-iodo-2-propynyl butyl carbannate 16 (IPBC) are combined with polymeric betaines such as didecyl bis(hydroxyethyl) ammonium borate 17 (DPAB), they form wood preservative compositions that are surprisingly more effective against 18 microorganisms that produce mold and/or sapstain on wood or wood products than either single 19 component alone. It has been found that in the combinations of this invention, the polymeric betaines and iodopropynyl compounds complement one another in a way that could not be anticipated. The 21 polymeric betaines and iodopropynl compound show synergistic activity.
This unexpected synergistic 22 activity offers a number of advantages in the preservation of wood and wood products.
23 This invention relates to the synergistic wood preservative composition comprising of polymeric 24 betaine, or more precisely didecyl bis(hydroxyethyl) ammonium borate (DPAB), and 3-iodo-2-propynyl butyl carbamate having the properties of providing effective and broader control of microorganisms that 26 produce mold and sapstain. Suitable polymeric betaines are described in, for example, U.S. Patent No.
27 5,304,237. The structural formula of DPAB is:
CH2CH, 0 CH2C112iõ,, .,,OCID1421 NI+
CH õ"
C.Ar cH2C1420 OCH2 2sr" CH
CPST Doc: 415843.2 Date Regue/Date Received 2022-08-04 CA 3,149,341 CPST Ref: 40659/00001 1 The antisapstain compositions of the invention can be prepared as solutions or emulsions by 2 conventional means by using water or organic liquids as a solvent. A
preferred form is to combine a 3 water solution of polymeric betaine and an organic solvent solution of IPBC. The process conditions for 4 the preparation of the composition of the invention are at ambient temperature.
The quantity and ratio of polymeric betaine and IPBC will depend upon the specific application.
6 Generally, the wood preservative composition will contain from about 1 to 100 parts by weight polymeric 7 betaine per about 1 to 100 parts by weight IPBC. More preferably, the composition will contain about 1 to 8 90, 1 to 80, 1 to 70, 1 to 60, 1 to 50, or 1 to 40 parts by weight of polymeric betaine per 1 to 90, 1 to 80, 1 9 to 70, 1 to 60, 1 to 50, or 1 to 40 parts by weight of IPBC. A preferred weight ratio of polymeric betaine to IPBC is from about 30:1 to about 1:30, more preferably 20:1 to 1:20, even more preferably 10:1 to 1:10.
11 A particularly preferred ratio of polymeric betaine to IPBC is from 5:1 to 10:1 parts by weight, i.e., about 5 12 to 10 parts by weight polymeric betaine per part by weight IPBC. Other preferred ratios of polymeric 13 betaine to IPBC include 1:1, 2:1 to 1:2, 3:2 to 2:3, 3:1 to 1:3,4:1 to 1:4, 4:3 to 3:4, 5:1 to 1:5, 5:2 to 2:5, 14 5:3 to 3:5, 5:4 to 4:5, 6:1 to 1:6, 6:5 to 5:6, 7:1 to 1:7, 7:2 to 2:7, 7:3 to 3:7, 7:4 to 4:7, 7:5 to 5:7, 7:6 to 6:7, 8:1 to 1:8, 8:3 to 3:8, 8:5 to 5:8, 8:7 to 7:8, 9:1 to 1:9, 9:2 to 2:9, 9:4 to 4:9, 9:5 to 5:9, 9:7 to 7:9, 9:8 16 to 8:9, 10:9 to 9:10, 10:7 to 7:10, and 10:3 to 3:10. Any of the upper limits of these ranges may be 17 combined with the lower limits of the other ranges, and vice-versa, in accordance with other aspects of 18 the invention.
19 It may be advantageous to supply the preservative composition in concentrated form with about 15, 20, 25, 30, 35, 40, or 45 percent by weight of solvent to about 50, 55, 60, 65, 70, 75, or 80 percent by 21 weight solvent. According to another aspect of the invention the composition may comprise more than 80 22 percent by weight of solvents, for example from 80 to 99.9, 85 to 99.9, 90 to 99.9, 90.5 to 99.9, 91 to 23 99.9, 91.5 to 99.9, 92 to 99.9, 92.5 to 99, 93 to 99.9, or 95 to 99.9 percent by weight of solvent. Typical 24 solvents include water and/or organic solvents, including aromatic organic solvents, polar and non-polar organic solvents, and aliphatic organic solvents.
26 The concentrate is generally diluted about 10 to 200 times to working solution strength by the 27 addition of water (or another solvent). The diluted solution or emulsion can be applied to wood by 28 conventional treating methods such as immersion, brush, spray, flooding, or pressure.
29 These antimicrobial mixtures provide a high level of activity over a prolonged period, providing the strengths of the individual ingredients while minimizing the weaknesses of each. It is this type of 31 complimentary activity that allows one to use less biocide in combination to achieve a desired effect at 32 levels that cannot be achieved with any of the individual ingredients.
33 The halopropynyl compounds that can be used in accordance with the present invention, for the 34 most part, are well known and can be generally identified by the following structure:
CPST Doc: 415843.2 Date Regue/Date Received 2022-08-04 CA 3,149,341 CPST Ref: 40659/00001 2 wherein Y is halogen, and X can be (1) oxygen that is part of an organic functional group; (2) nitrogen that 3 is part of an organic functional group; (3) sulfur that is part of an organic functional group; or (4) carbon 4 that is part of an organic functional group.
The functional group of which oxygen is a part, is preferably an ether, an ester, or a carbamate 6 group. The functional group of which nitrogen is a part is preferably an amine, an amide, or a carbamate 7 group. The functional group of which sulfur is a part is preferably a thiol, a thiane, a sulfone, or a sulfoxide 8 group. The organic functional group of which carbon is a part is preferably an ester, a carbamate or an 9 alkyl group.
Examples of compounds that may be used as the halopropynyl compound of this invention are 11 especially the active iodopropynyl derivatives some of which are reported in U.S. Pat. Nos. 3,923,870;
12 4,259,350; 4,592,773; 4,616,004; 4,719,227; and 4,945,109. These iodopropynyl derivatives include 13 compounds derived from propynyl or iodopropynyl alcohols such as esters, acetals, carbamates and 14 carbonates and further include the iodopropynyl derivatives of pyrimidines, thiazolinones, tetrazoles, triazolones, sulfannides, benzothiazoles, ammonium salts, carboxamides, and ureas. The preferred and 16 most widely used among these compounds is the halopropynyl carbamate, 3-iodo-2-propynyl butyl 17 carbamate. These compounds are included within the useful class of compounds having the generic 18 formula:
rt( ( AMIN , .7...011111--** ( 19 i wherein R may have one to three linkages corresponding to n and is selected from the group consisting 21 of hydrogen, substituted and unsubstituted alkyl groups having from 1 to 20 carbon atoms, substituted 22 and unsubstituted aryl, alkylaryl, and aralkyl of from 6 to 20 carbon atoms or cycloalkyl and cycloalkenyl 23 groups of from 3 to 10 carbon atoms, and m and n are independently integers from 1 to 3, i.e., they are 24 not necessarily the same.
Particularly preferred are formulations of such halopropynyl carbamates where m is 1 and n is 1 26 and which have the following formula:
CPST Doc: 415843.2 Date Regue/Date Received 2022-08-04 CA 3,149,341 CPST Ref: 40659/00001 1 Suitable R substituents include alkyls such as methyl, ethyl, propyl, n-butyl, t-butyl, pentyl, hexyl, heptyl, 2 .. octyl, nonyl, decyl, dodecyl, and octadecyl; cycloalkyls such as cyclohexyl; aryls, alkaryls and aralkyls 3 such as phenyl, benzyl, tolyl, and cumyl; halogenated alkyls and aryls, such as chlorobutyl and 4 .. chlorophenyl; and alkoxy aryls such as ethoxyphenyl and the like.
Especially preferred are such iodopropynyl carbamates as 3-iodo-2-propynyl propyl carbamate, 6 3-iodo-2-propynyl butyl carbamate, 3-iodo-2-propynyl hexyl carbamate, 3-iodo-2-propynyl cyclohexyl 7 carbamate, 3-iodo-2-propynyl phenyl carbamate, and mixtures thereof.
8 Compositions of the present invention will generally be formulated by mixing or dispersing the 9 active ingredients in a selected proportion with a liquid vehicle for dissolving or suspending the active .. components. The vehicle may contain a diluent, an emulsifier, and a wetting-agent. Expected uses of 11 the biocidal compositions include the protection of wood, wood products, fresh sawn timber, and the like.
12 The compositions of this invention may be provided as liquid mixtures such as dispersions, emulsions, 13 microemulsions, or in any other suitable product form that is desirable or most useful.
14 When preparing formulations of the present invention for specific applications, the composition also will likely be provided with adjuvants conventionally employed in compositions intended for such 16 applications such as organic binding agents, additional fungicides, auxiliary solvents, processing 17 additives, fixatives, plasticizers, UV-stabilizers or stability enhancers, water soluble or water insoluble 18 dyes, color pigments, siccatives, corrosion inhibitors, antisettlement agents, anti-skinning agents and the 19 like.
According to the present invention, substrates are protected from contamination by 21 microorganisms simply by treating said substrate with a composition of the present invention. Such 22 treating may involve mixing the composition with the substrate, coating or otherwise contacting the 23 substrate with the composition and the like.
24 The following example is presented to illustrate and explain the invention. Unless otherwise indicated, all references to parts and percentages are based on weight.
26 Example 1 27 To show the efficacy of the composition of the invention on wood deteriorating microorganisms, 28 the following solutions were prepared:
29 (A) 0.17 g of 60% DPAB aqueous solution (ProTek PBT or Polymeric Betaine EP or Polymeric Betaine Technical Grade Active Ingredient Wood Preservative, Troy Chemical Corporation, Newark, NJ) 31 was diluted in 9.83 g ethanol by stirring to form a concentrate containing 1% DPAB.
32 (B) 0.25 g of 40% IPBC solvent solution (Polyphase AF-1, Troy Chemical Corporation, Newark, NJ) 33 was diluted in 9.75 g ethanol by stirring to form a concentrate containing 1% IPBC.
34 (C) 21.04 g of 60% DPAB aqueous solution (ProTek PBT or Polymeric Betaine EP or Polymeric Betaine Technical Grade Active Ingredient Wood Preservative, Troy Chemical Corporation, Newark, NJ),
The present application claims priority to U.S. Patent Application No.
62/884,738, filed August 9, 6 2019, entitled "SYNERGISTIC WOOD PRESERVATIVE COMPOSITION COMPRISING
POLYMERIC
7 BETAINE AND CARBAMATE".
1. Field of the Invention 11 The present invention pertains to synergistic compositions suitable for use in the treatment and 12 preservation of wood and wood products. The antimicrobial compositions of this invention include wood 13 preservative compositions comprising a polymeric betaine and an iodopropynyl compound. These 14 combinations are especially useful in protecting wood and wood products from spoilage resulting from the growth of microorganisms, especially microorganisms that produce mold and sapstain.
16 2. Description of the Background 17 Substrates of all types, when exposed to common environmental conditions, are prone to attack, 18 spoilage and various kinds of destruction by a variety of species of microorganisms including fungi, yeast, 19 bacteria, algae, and mold. As a result, there has always been a great need for effective and economical means to protect various materials, for extended periods of time, from the defacement, deterioration, and 21 destruction caused by such microorganisms. Materials that need protection against such microorganisms 22 include, for example, wood and wood products, which are prone to degradation by the action of 23 objectionable microorganisms. Such degradation may produce, inter alia, deterioration, discoloration, the 24 formation of objectionable odors, and other adverse effects on the substrate.
A great deal of effort has gone into developing a wide variety of materials which, to various 26 degrees, are effective in retarding or preventing the growth of, and accompanying destruction caused by, 27 such microorganisms in a variety of circumstances. Such antimicrobial materials included halogenated 28 compounds, organometallic compounds, quaternary ammonium compounds, phenolics, metallic salts, 29 heterocyclic amines, formaldehyde adducts, organosulfur compounds, and the like.
No single organic antimicrobial compound is able to provide protection against all microorganisms 31 and is suitable for all applications. In addition to such limitations concerning efficacy, other limitations 32 may restrict the usefulness of certain antimicrobials. For example the stability, physical properties, 33 toxicological profile, regulatory considerations, economic considerations or environmental concerns may 34 render a particular ingredient unsuitable for a particular use. There is a need, therefore, to constantly develop new combinations that will offer broad spectrum protection from a variety of needs.
CPST Doc: 415843.2 Date Regue/Date Received 2022-08-04 CA 3,149,341 CPST Ref: 40659/00001 1 A judicious choice of combinations may provide a way to maximize benefits while at the same 2 time minimize problems. Ideally, a combination wherein the antimicrobial activity is enhanced while the 3 less desirable properties are suppressed or reduced can provide a superior product. The task is to find 4 such combinations that will provide protection against a wide variety of problem microorganisms, will not adversely affect the product to be protected, will maintain its integrity for an extended period of time, and 6 will not have any strong adverse effects on health or the environment.
9 The present invention is directed to certain synergistic preservative compositions comprising a polymeric betaine and an iodopropynyl compound. The present invention is also directed to methods for 11 controlling mold and/or sapstain on wood or wood products by application of an effective amount of such 12 compositions to the wood or wood product substrate.
It has been found that when iodopropynyl compounds such as 3-iodo-2-propynyl butyl carbannate 16 (IPBC) are combined with polymeric betaines such as didecyl bis(hydroxyethyl) ammonium borate 17 (DPAB), they form wood preservative compositions that are surprisingly more effective against 18 microorganisms that produce mold and/or sapstain on wood or wood products than either single 19 component alone. It has been found that in the combinations of this invention, the polymeric betaines and iodopropynyl compounds complement one another in a way that could not be anticipated. The 21 polymeric betaines and iodopropynl compound show synergistic activity.
This unexpected synergistic 22 activity offers a number of advantages in the preservation of wood and wood products.
23 This invention relates to the synergistic wood preservative composition comprising of polymeric 24 betaine, or more precisely didecyl bis(hydroxyethyl) ammonium borate (DPAB), and 3-iodo-2-propynyl butyl carbamate having the properties of providing effective and broader control of microorganisms that 26 produce mold and sapstain. Suitable polymeric betaines are described in, for example, U.S. Patent No.
27 5,304,237. The structural formula of DPAB is:
CH2CH, 0 CH2C112iõ,, .,,OCID1421 NI+
CH õ"
C.Ar cH2C1420 OCH2 2sr" CH
CPST Doc: 415843.2 Date Regue/Date Received 2022-08-04 CA 3,149,341 CPST Ref: 40659/00001 1 The antisapstain compositions of the invention can be prepared as solutions or emulsions by 2 conventional means by using water or organic liquids as a solvent. A
preferred form is to combine a 3 water solution of polymeric betaine and an organic solvent solution of IPBC. The process conditions for 4 the preparation of the composition of the invention are at ambient temperature.
The quantity and ratio of polymeric betaine and IPBC will depend upon the specific application.
6 Generally, the wood preservative composition will contain from about 1 to 100 parts by weight polymeric 7 betaine per about 1 to 100 parts by weight IPBC. More preferably, the composition will contain about 1 to 8 90, 1 to 80, 1 to 70, 1 to 60, 1 to 50, or 1 to 40 parts by weight of polymeric betaine per 1 to 90, 1 to 80, 1 9 to 70, 1 to 60, 1 to 50, or 1 to 40 parts by weight of IPBC. A preferred weight ratio of polymeric betaine to IPBC is from about 30:1 to about 1:30, more preferably 20:1 to 1:20, even more preferably 10:1 to 1:10.
11 A particularly preferred ratio of polymeric betaine to IPBC is from 5:1 to 10:1 parts by weight, i.e., about 5 12 to 10 parts by weight polymeric betaine per part by weight IPBC. Other preferred ratios of polymeric 13 betaine to IPBC include 1:1, 2:1 to 1:2, 3:2 to 2:3, 3:1 to 1:3,4:1 to 1:4, 4:3 to 3:4, 5:1 to 1:5, 5:2 to 2:5, 14 5:3 to 3:5, 5:4 to 4:5, 6:1 to 1:6, 6:5 to 5:6, 7:1 to 1:7, 7:2 to 2:7, 7:3 to 3:7, 7:4 to 4:7, 7:5 to 5:7, 7:6 to 6:7, 8:1 to 1:8, 8:3 to 3:8, 8:5 to 5:8, 8:7 to 7:8, 9:1 to 1:9, 9:2 to 2:9, 9:4 to 4:9, 9:5 to 5:9, 9:7 to 7:9, 9:8 16 to 8:9, 10:9 to 9:10, 10:7 to 7:10, and 10:3 to 3:10. Any of the upper limits of these ranges may be 17 combined with the lower limits of the other ranges, and vice-versa, in accordance with other aspects of 18 the invention.
19 It may be advantageous to supply the preservative composition in concentrated form with about 15, 20, 25, 30, 35, 40, or 45 percent by weight of solvent to about 50, 55, 60, 65, 70, 75, or 80 percent by 21 weight solvent. According to another aspect of the invention the composition may comprise more than 80 22 percent by weight of solvents, for example from 80 to 99.9, 85 to 99.9, 90 to 99.9, 90.5 to 99.9, 91 to 23 99.9, 91.5 to 99.9, 92 to 99.9, 92.5 to 99, 93 to 99.9, or 95 to 99.9 percent by weight of solvent. Typical 24 solvents include water and/or organic solvents, including aromatic organic solvents, polar and non-polar organic solvents, and aliphatic organic solvents.
26 The concentrate is generally diluted about 10 to 200 times to working solution strength by the 27 addition of water (or another solvent). The diluted solution or emulsion can be applied to wood by 28 conventional treating methods such as immersion, brush, spray, flooding, or pressure.
29 These antimicrobial mixtures provide a high level of activity over a prolonged period, providing the strengths of the individual ingredients while minimizing the weaknesses of each. It is this type of 31 complimentary activity that allows one to use less biocide in combination to achieve a desired effect at 32 levels that cannot be achieved with any of the individual ingredients.
33 The halopropynyl compounds that can be used in accordance with the present invention, for the 34 most part, are well known and can be generally identified by the following structure:
CPST Doc: 415843.2 Date Regue/Date Received 2022-08-04 CA 3,149,341 CPST Ref: 40659/00001 2 wherein Y is halogen, and X can be (1) oxygen that is part of an organic functional group; (2) nitrogen that 3 is part of an organic functional group; (3) sulfur that is part of an organic functional group; or (4) carbon 4 that is part of an organic functional group.
The functional group of which oxygen is a part, is preferably an ether, an ester, or a carbamate 6 group. The functional group of which nitrogen is a part is preferably an amine, an amide, or a carbamate 7 group. The functional group of which sulfur is a part is preferably a thiol, a thiane, a sulfone, or a sulfoxide 8 group. The organic functional group of which carbon is a part is preferably an ester, a carbamate or an 9 alkyl group.
Examples of compounds that may be used as the halopropynyl compound of this invention are 11 especially the active iodopropynyl derivatives some of which are reported in U.S. Pat. Nos. 3,923,870;
12 4,259,350; 4,592,773; 4,616,004; 4,719,227; and 4,945,109. These iodopropynyl derivatives include 13 compounds derived from propynyl or iodopropynyl alcohols such as esters, acetals, carbamates and 14 carbonates and further include the iodopropynyl derivatives of pyrimidines, thiazolinones, tetrazoles, triazolones, sulfannides, benzothiazoles, ammonium salts, carboxamides, and ureas. The preferred and 16 most widely used among these compounds is the halopropynyl carbamate, 3-iodo-2-propynyl butyl 17 carbamate. These compounds are included within the useful class of compounds having the generic 18 formula:
rt( ( AMIN , .7...011111--** ( 19 i wherein R may have one to three linkages corresponding to n and is selected from the group consisting 21 of hydrogen, substituted and unsubstituted alkyl groups having from 1 to 20 carbon atoms, substituted 22 and unsubstituted aryl, alkylaryl, and aralkyl of from 6 to 20 carbon atoms or cycloalkyl and cycloalkenyl 23 groups of from 3 to 10 carbon atoms, and m and n are independently integers from 1 to 3, i.e., they are 24 not necessarily the same.
Particularly preferred are formulations of such halopropynyl carbamates where m is 1 and n is 1 26 and which have the following formula:
CPST Doc: 415843.2 Date Regue/Date Received 2022-08-04 CA 3,149,341 CPST Ref: 40659/00001 1 Suitable R substituents include alkyls such as methyl, ethyl, propyl, n-butyl, t-butyl, pentyl, hexyl, heptyl, 2 .. octyl, nonyl, decyl, dodecyl, and octadecyl; cycloalkyls such as cyclohexyl; aryls, alkaryls and aralkyls 3 such as phenyl, benzyl, tolyl, and cumyl; halogenated alkyls and aryls, such as chlorobutyl and 4 .. chlorophenyl; and alkoxy aryls such as ethoxyphenyl and the like.
Especially preferred are such iodopropynyl carbamates as 3-iodo-2-propynyl propyl carbamate, 6 3-iodo-2-propynyl butyl carbamate, 3-iodo-2-propynyl hexyl carbamate, 3-iodo-2-propynyl cyclohexyl 7 carbamate, 3-iodo-2-propynyl phenyl carbamate, and mixtures thereof.
8 Compositions of the present invention will generally be formulated by mixing or dispersing the 9 active ingredients in a selected proportion with a liquid vehicle for dissolving or suspending the active .. components. The vehicle may contain a diluent, an emulsifier, and a wetting-agent. Expected uses of 11 the biocidal compositions include the protection of wood, wood products, fresh sawn timber, and the like.
12 The compositions of this invention may be provided as liquid mixtures such as dispersions, emulsions, 13 microemulsions, or in any other suitable product form that is desirable or most useful.
14 When preparing formulations of the present invention for specific applications, the composition also will likely be provided with adjuvants conventionally employed in compositions intended for such 16 applications such as organic binding agents, additional fungicides, auxiliary solvents, processing 17 additives, fixatives, plasticizers, UV-stabilizers or stability enhancers, water soluble or water insoluble 18 dyes, color pigments, siccatives, corrosion inhibitors, antisettlement agents, anti-skinning agents and the 19 like.
According to the present invention, substrates are protected from contamination by 21 microorganisms simply by treating said substrate with a composition of the present invention. Such 22 treating may involve mixing the composition with the substrate, coating or otherwise contacting the 23 substrate with the composition and the like.
24 The following example is presented to illustrate and explain the invention. Unless otherwise indicated, all references to parts and percentages are based on weight.
26 Example 1 27 To show the efficacy of the composition of the invention on wood deteriorating microorganisms, 28 the following solutions were prepared:
29 (A) 0.17 g of 60% DPAB aqueous solution (ProTek PBT or Polymeric Betaine EP or Polymeric Betaine Technical Grade Active Ingredient Wood Preservative, Troy Chemical Corporation, Newark, NJ) 31 was diluted in 9.83 g ethanol by stirring to form a concentrate containing 1% DPAB.
32 (B) 0.25 g of 40% IPBC solvent solution (Polyphase AF-1, Troy Chemical Corporation, Newark, NJ) 33 was diluted in 9.75 g ethanol by stirring to form a concentrate containing 1% IPBC.
34 (C) 21.04 g of 60% DPAB aqueous solution (ProTek PBT or Polymeric Betaine EP or Polymeric Betaine Technical Grade Active Ingredient Wood Preservative, Troy Chemical Corporation, Newark, NJ),
5 CPST Doc: 415843.2 Date Regue/Date Received 2022-08-04 CA 3,149,341 CPST Ref: 40659/00001 1 6.25 g of 40% IPBC solvent solution (Polyphase AF-1, Troy Chemical Corporation, Newark, NJ) and 2 22.74 g of ethanol were mixed and stirred. The resulting concentrate contained 25% polymeric betaine 3 and 5% IPBC. The weight ratio of polymeric betaine to IPBC was 5:1. 0.33 g of this IPBC/polymeric 4 betaine concentrate was diluted in 9.67 g of ethanol to form a use-dilution containing about 0.83% DPAB
and 0.17% IPBC.
and 0.17% IPBC.
6 Solutions prepared as described above were tested in 96-well plates for their ability to inhibit
7 fungal growth. The solutions were tested according to the EUCAST
methodology as described in
methodology as described in
8 Rodriguez-Tudela et al. 2006 "Antifungal susceptibility testing in Aspergillus spp. according to EUCAST
9 methodology.". The solutions were checked for inhibition against fungal organisms Aspergillus niger (ATCC# 6275), Aureobasidium pullulans (ATCC# 9348), Peniciffium funiculosum (ATCC# 11797) and 11 Trichoderma pseudokoningii (ATCC# 26801). This method is briefly described below:
12 (1) Prepared preservative test wells by adding 2 microliters of each 1% preservative solution 13 formulation to 198 microliters of 2xRPM I-MOPS-2% Glucose in each column "1" in duplicate.
14 (2) Added 100 microliters of 2xRPMI-MOPS-2% Glucose to the remaining columns.
(3) Performed 2-fold dilutions down the columns to column "12".
16 (4) Prepared suspension of microorganisms from a 3-5 day old PDA
slants by flooding slant with 1 17 mL deionized water and 0.1% Tween-20.
18 (5) Suspension strength was determined via hemocytometer then adjusted to lx106spores/mL with 19 sterile deionized water.
(6) Added 100 microliters of the microorganism suspension to all wells except for sterility (-) controls 21 containing test media. The water used to prepare the fungal suspensions was added to sterility (-) control 22 wells.
23 (7) The inoculated 96-well plates were incubated for 3 days at 35 C.
24 (8) After incubation, fungal growth was evaluated by visual growth in test wells. Minimum inhibitory concentration (MIC) is recorded in ppm and defined as the lowest concentration of fungicide that 26 produces no visual changes in turbidity in the test wells.
27 (9) The experiment is only considered valid if growth is observed in the positive (+) control wells and 28 no growth is observed in the negative control wells.
29 The effectiveness on all four examined microorganisms is presented in Tables 1 to 4.
Table 1. The growth of Aspetwillus niper (ATCC# 6275) in 96-well plates containing selected concentrations of DPAB, IPBC and their mixture. The values stated wells 1 through 12 are in ppm active.
Test solutions al. 1 2 3 4 5 6 7 8 9 10 11 __ 12 CPST Doc: 415843.2 Date Regue/Date Received 2022-08-04 CA 3,149,341 CPST Ref: 40659/00001 0,0 A 1% IPBC 50.00 25.00 12.50 6.25 3.13 1.56 0.78 '110.39 0.10' 5' 0.62 '14111('0.0 B 1% IPBC 50.00 25.00 12.50 6.25 3.13 1.56 0.78 0.39 020 0.10 , , 5
12 (1) Prepared preservative test wells by adding 2 microliters of each 1% preservative solution 13 formulation to 198 microliters of 2xRPM I-MOPS-2% Glucose in each column "1" in duplicate.
14 (2) Added 100 microliters of 2xRPMI-MOPS-2% Glucose to the remaining columns.
(3) Performed 2-fold dilutions down the columns to column "12".
16 (4) Prepared suspension of microorganisms from a 3-5 day old PDA
slants by flooding slant with 1 17 mL deionized water and 0.1% Tween-20.
18 (5) Suspension strength was determined via hemocytometer then adjusted to lx106spores/mL with 19 sterile deionized water.
(6) Added 100 microliters of the microorganism suspension to all wells except for sterility (-) controls 21 containing test media. The water used to prepare the fungal suspensions was added to sterility (-) control 22 wells.
23 (7) The inoculated 96-well plates were incubated for 3 days at 35 C.
24 (8) After incubation, fungal growth was evaluated by visual growth in test wells. Minimum inhibitory concentration (MIC) is recorded in ppm and defined as the lowest concentration of fungicide that 26 produces no visual changes in turbidity in the test wells.
27 (9) The experiment is only considered valid if growth is observed in the positive (+) control wells and 28 no growth is observed in the negative control wells.
29 The effectiveness on all four examined microorganisms is presented in Tables 1 to 4.
Table 1. The growth of Aspetwillus niper (ATCC# 6275) in 96-well plates containing selected concentrations of DPAB, IPBC and their mixture. The values stated wells 1 through 12 are in ppm active.
Test solutions al. 1 2 3 4 5 6 7 8 9 10 11 __ 12 CPST Doc: 415843.2 Date Regue/Date Received 2022-08-04 CA 3,149,341 CPST Ref: 40659/00001 0,0 A 1% IPBC 50.00 25.00 12.50 6.25 3.13 1.56 0.78 '110.39 0.10' 5' 0.62 '14111('0.0 B 1% IPBC 50.00 25.00 12.50 6.25 3.13 1.56 0.78 0.39 020 0.10 , , 5
10 02 %
111, 0.0, C 1% DPAB 50.00 25.00 12.50 '16.25 3.13 1.56 'b.78 0.39 0.20, 0 10 5 "" 10.02"
0.6- '1111' D 1% DPAB 50.00 25.00 12.50 625 3.16 1.56 0.7877 0.39õ 0.20,õ 0.10 ,15 1110,02 1' 71117 111,1 ,111 0,197 E 1% (IPBC + DPAB) 50.00 25.00 12.50 6.25 3.13 11.56 0.78 01a,911 16,201 610,5 0.02 0.0 F 1% (IPBC + DPAB) 50.00 25.00 12.50 6.25 3.13 1 56 0.78' 0.39:- 0.20,- oio,' 5 1110.02 G Controls + + + + + + _ _ _ _ _ Table 2. The growth of Aureobasidium pullulans (ATCC# 9348) in 96-well plates containing selected concentrations of DPAB, IPBC
and their mixture. The values stated wells 1 through 12 are in ppm active.
I Test solutions a.i. 1 2 3 4 5 6 7 8 9 10
111, 0.0, C 1% DPAB 50.00 25.00 12.50 '16.25 3.13 1.56 'b.78 0.39 0.20, 0 10 5 "" 10.02"
0.6- '1111' D 1% DPAB 50.00 25.00 12.50 625 3.16 1.56 0.7877 0.39õ 0.20,õ 0.10 ,15 1110,02 1' 71117 111,1 ,111 0,197 E 1% (IPBC + DPAB) 50.00 25.00 12.50 6.25 3.13 11.56 0.78 01a,911 16,201 610,5 0.02 0.0 F 1% (IPBC + DPAB) 50.00 25.00 12.50 6.25 3.13 1 56 0.78' 0.39:- 0.20,- oio,' 5 1110.02 G Controls + + + + + + _ _ _ _ _ Table 2. The growth of Aureobasidium pullulans (ATCC# 9348) in 96-well plates containing selected concentrations of DPAB, IPBC
and their mixture. The values stated wells 1 through 12 are in ppm active.
I Test solutions a.i. 1 2 3 4 5 6 7 8 9 10
11 12 A. 1% IPBC 50.00 25.00 12.50 6.25 3.13 , 1.56 0.78', 0.39'' 0.20 0.10 005 - 0.02 B 1% IPBC 50.00 25.00 12.50 625 3.13 1.56 0.78 0.39 0.20 0.10 - 0.05 0.02 , C 1% DPAB 50.00 25.00 12.50 6257" 311,13, 115,6,' 11618' l'6,,3911' ,I16,10 0.05 0.02 D 1% DPAB 50.00 25.00 12.50 16.25 3.13 '1.56 0.78, 0.69 6.20 0.10 0.05 0.02 E 1% (IPBC + DPAB) 50.00 25.00 12.50 6.25 3.13 1.56 0.78 0.39 0 20 0 10 0.05 f 0.02 F 1% (IPBC + DPAB) 50.00 25.00 12.50 6.25 3.13 1.56 0.78 0.39 0.20 0.10 0.05 0.02 G Controls - - -Table 3. The growth of Penldrnum funiculosum (ATCC# 11797) in 96-well plates containinq selected concentrations of DPAB, IPBC
and their mixture.
I I I Test solutions a.i. 1 2 3 4 5 6 7 A 1% IPBC 50.00 25.00 12.50 6.25 3.13 1.56 0.78 0.39 0.20 010 0.05 0.02 1-=
B 1% IPBC 50.00 25.00 12.50 6.25 3.13 1.56 0.78 0.39 0.20 0.10 0.05 0.02 C 1% DPAB 50.00 25.00 12.50 6.25 313 156 0,78 0.39 020 010 0.05 002 D 1% DPAB 50.00 25.00 12.50 6.25 313 1.55 0.78 0.39 0.20 010 005 002 E 1% (IPBC + DPAB) 50.00 25.00 12.50 6.25 3.13 1 1.56 0.78 0.391 0'.20 0.10 0.05 0.02 F 1% (IPBC + DPAB) I 50.00 25.00 12.50 6.25 3.13 1-.55- 0.78 0.39 -6.2-6- 0.1-6----0105 0 02 _ G Controls +
+ 1 + 1 Table 4. The growth of Trichoderma pseudokoninqii (ATCC# 26801) in 96-well plates containing selected concentrations of DPABt IPBC and their mixture. The values stated wells 1 through 12 are in ppm active.
CPST Doc: 415843.2 Date Recue/Date Received 2022-08-04 CA 3,149,341 CPST Ref: 40659/00001 ID Test solutions a.i. 1 2 3 4 5 6 7 8 9 10 A 1% IPBC 50.00 25.00 12.50 6.25 313 156 078 039 , 020 :010 0,05 002 B 1% IPBC 50.00 25.00 12.50 6.25 313 1.56 0.78 0.39 0.20 0.10 0.05 0.02 C 1% DPAB 50.00 25.00 12.50 6.25 3.13 1.56 0.78 0.39 0.20 0 10 0.05 0.02 D 1% DPAB 50.00 25.00 12 50 6.25 3 13 1.56 0.78 . 0.39 I 0.20 0.10 0.05 0.02 E 1% (IPBC + DPAB) 50.00 25.00 12.50 6.25 3 13 1.56 0 /8 039 0.20 0.10 0.05 002 F 1% (IPBC + DPAB) 50.00 25.00 12.50 6.25 3.13 1.56 0.78 0.39 0.20 0 10 0.05 0.02 G Controls In order to show more directly the possible synergy in the invention, the results are presented by applying the Synergy Index (S.I.). Minimal inhibitory concentration of the composition of this invention (mixture of DPAB
and IPBC) are analyzed using the following equation:
(MCAMICA) + (MCB'/MCB) = SI
Wherein:
MCA = Concentration of compound A in parts per million, acting alone, which prevents fungal growth at the reference point MCA' = Concentration of compound A in parts per million, in the mixture, which prevents fungal growth at the reference point MCB = Concentration of compound B in parts per million, acting alone, which prevents fungal growth at the reference point MCB' = Concentration of compound B in parts per million, in the mixture, which prevents fungal growth at the reference point When SI is greater than 2, antagonism is indicated. When SI is less than 0.5, synergy is demonstrated. When SI is between 0.5 and 2, the action of biocides is additive.
Table 5 represents an anti-fungal activity of IPBC, DPAB, and their mixture at 1:5, respectively. The simultaneous activity of the two actives is expressed as Synergy Index.
Table 5. Synergistic anti-fungal activity of IPBC and DPAB
Microorganisms ATCC MIC (ppm) Synergy IPBC DPAB IPBC/DPAB (Ratio Index of 1:5) Aspergillus niger 6275 0.78 12.50 3.13 0.88 Aureobasidium pullulans 9348 25.00 12.5 6.25 0.46 Penicillium funiculosum 11797 0.78 6.25 3.13 1.08 Trichoderma pseudokoningii 26801 6.25 25.00 6.25 0.38 These tests clearly demonstrate that the combination of polymeric betaine (DPAB) and IPBC
provided significantly unexpectedly greater protection against the sapstain organism Aureabasidium 4 pullulans and the mold organism Trichoderma sp. than treatments of either of the two components taken alone.
CPST Doc: 415843.2 Date Regue/Date Received 2022-08-04 CA 3,149,341 CPST Ref: 40659/00001 1 While the invention has been particularly described in terms of specific embodiments, those 2 skilled in the art will understand in view of the present disclosure that numerous variations and 3 modifications upon the invention are now enabled, which variations and modifications are not to be 4 regarded as a departure from the spirit and scope of the invention.
Accordingly, the invention is to be broadly construed and limited only by the scope and spirit of the following claims.
CPST Doc: 415843.2 Date Regue/Date Received 2022-08-04
and their mixture.
I I I Test solutions a.i. 1 2 3 4 5 6 7 A 1% IPBC 50.00 25.00 12.50 6.25 3.13 1.56 0.78 0.39 0.20 010 0.05 0.02 1-=
B 1% IPBC 50.00 25.00 12.50 6.25 3.13 1.56 0.78 0.39 0.20 0.10 0.05 0.02 C 1% DPAB 50.00 25.00 12.50 6.25 313 156 0,78 0.39 020 010 0.05 002 D 1% DPAB 50.00 25.00 12.50 6.25 313 1.55 0.78 0.39 0.20 010 005 002 E 1% (IPBC + DPAB) 50.00 25.00 12.50 6.25 3.13 1 1.56 0.78 0.391 0'.20 0.10 0.05 0.02 F 1% (IPBC + DPAB) I 50.00 25.00 12.50 6.25 3.13 1-.55- 0.78 0.39 -6.2-6- 0.1-6----0105 0 02 _ G Controls +
+ 1 + 1 Table 4. The growth of Trichoderma pseudokoninqii (ATCC# 26801) in 96-well plates containing selected concentrations of DPABt IPBC and their mixture. The values stated wells 1 through 12 are in ppm active.
CPST Doc: 415843.2 Date Recue/Date Received 2022-08-04 CA 3,149,341 CPST Ref: 40659/00001 ID Test solutions a.i. 1 2 3 4 5 6 7 8 9 10 A 1% IPBC 50.00 25.00 12.50 6.25 313 156 078 039 , 020 :010 0,05 002 B 1% IPBC 50.00 25.00 12.50 6.25 313 1.56 0.78 0.39 0.20 0.10 0.05 0.02 C 1% DPAB 50.00 25.00 12.50 6.25 3.13 1.56 0.78 0.39 0.20 0 10 0.05 0.02 D 1% DPAB 50.00 25.00 12 50 6.25 3 13 1.56 0.78 . 0.39 I 0.20 0.10 0.05 0.02 E 1% (IPBC + DPAB) 50.00 25.00 12.50 6.25 3 13 1.56 0 /8 039 0.20 0.10 0.05 002 F 1% (IPBC + DPAB) 50.00 25.00 12.50 6.25 3.13 1.56 0.78 0.39 0.20 0 10 0.05 0.02 G Controls In order to show more directly the possible synergy in the invention, the results are presented by applying the Synergy Index (S.I.). Minimal inhibitory concentration of the composition of this invention (mixture of DPAB
and IPBC) are analyzed using the following equation:
(MCAMICA) + (MCB'/MCB) = SI
Wherein:
MCA = Concentration of compound A in parts per million, acting alone, which prevents fungal growth at the reference point MCA' = Concentration of compound A in parts per million, in the mixture, which prevents fungal growth at the reference point MCB = Concentration of compound B in parts per million, acting alone, which prevents fungal growth at the reference point MCB' = Concentration of compound B in parts per million, in the mixture, which prevents fungal growth at the reference point When SI is greater than 2, antagonism is indicated. When SI is less than 0.5, synergy is demonstrated. When SI is between 0.5 and 2, the action of biocides is additive.
Table 5 represents an anti-fungal activity of IPBC, DPAB, and their mixture at 1:5, respectively. The simultaneous activity of the two actives is expressed as Synergy Index.
Table 5. Synergistic anti-fungal activity of IPBC and DPAB
Microorganisms ATCC MIC (ppm) Synergy IPBC DPAB IPBC/DPAB (Ratio Index of 1:5) Aspergillus niger 6275 0.78 12.50 3.13 0.88 Aureobasidium pullulans 9348 25.00 12.5 6.25 0.46 Penicillium funiculosum 11797 0.78 6.25 3.13 1.08 Trichoderma pseudokoningii 26801 6.25 25.00 6.25 0.38 These tests clearly demonstrate that the combination of polymeric betaine (DPAB) and IPBC
provided significantly unexpectedly greater protection against the sapstain organism Aureabasidium 4 pullulans and the mold organism Trichoderma sp. than treatments of either of the two components taken alone.
CPST Doc: 415843.2 Date Regue/Date Received 2022-08-04 CA 3,149,341 CPST Ref: 40659/00001 1 While the invention has been particularly described in terms of specific embodiments, those 2 skilled in the art will understand in view of the present disclosure that numerous variations and 3 modifications upon the invention are now enabled, which variations and modifications are not to be 4 regarded as a departure from the spirit and scope of the invention.
Accordingly, the invention is to be broadly construed and limited only by the scope and spirit of the following claims.
CPST Doc: 415843.2 Date Regue/Date Received 2022-08-04
Claims (12)
1. A synergistic wood preservation composition comprising a polymeric betaine and 3-iodo-2-propynyl butyl carbamate (IPBC).
2. The composition of claim 1, wherein the polymeric betaine comprises didecyl bis(hydroxyethyl) ammonium borate (DPAB).
3. A method of controlling microorganisms that produce mold and/or sapstain on wood or wood products comprising applying to a wood or wood product an amount of the composition of claim 1 effective to control the microorganisms.
4. The composition of claim 1, further comprising an aqueous solvent, an organic solvent, or any mixture thereof.
5. The composition of claim 4, in the form of a solution or an emulsion.
6. The composition of claim 1, comprising an aqueous solution of the polymeric betaine and an organic solution of the IPBC.
7. The composition of claim 1, comprising about 1 to about 100 parts by weight of the polymeric betaine per about 1 to about 10 parts by weight of the IPBC.
8. The composition of claim 7, comprising about 5 to about 10 parts by weight of the polymeric betaine per about 1 part by weight of the IPBC.
9. The composition of claim 4, comprising about 15 to about 80 weight percent of the solvent or mixture of solvents.
10. The composition of claim 4, wherein the solvent or solvents are selected from the group consisting of water, aromatic solvents, polar solvents, and aliphatic solvents.
11. The composition of claim 4, comprising about 91.5 to about 99.9 weight percent of the solvent or mixture of solvents.
12. The method of claim 3, wherein the composition is applied to the wood or wood product by one or more of immersion, brush, spray, flooding, or pressure.
Applications Claiming Priority (3)
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| US201962884738P | 2019-08-09 | 2019-08-09 | |
| US62/884,738 | 2019-08-09 | ||
| PCT/US2020/045452 WO2021030202A1 (en) | 2019-08-09 | 2020-08-07 | Synergistic wood preservative composition comprising polymeric betaine and carbamate |
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| CA3149341A1 CA3149341A1 (en) | 2021-02-18 |
| CA3149341C true CA3149341C (en) | 2024-03-05 |
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| CA3149341A Active CA3149341C (en) | 2019-08-09 | 2020-08-07 | Synergistic wood preservative composition comprising polymeric betaine and carbamate |
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|---|---|
| EP (1) | EP4009791A1 (en) |
| JP (1) | JP2022543694A (en) |
| KR (1) | KR20220044326A (en) |
| CN (1) | CN114206112B (en) |
| AU (1) | AU2020327938A1 (en) |
| BR (1) | BR112022001840A2 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3923870A (en) * | 1973-07-11 | 1975-12-02 | Troy Chemical Corp | Urethanes of 1-halogen substituted alkynes |
| CA1116622A (en) | 1978-03-15 | 1982-01-19 | Yasuhiro Morisawa | Iodopropargyl derivatives their use and preparation |
| IL75979A (en) | 1984-08-10 | 1988-10-31 | Mitsui Toatsu Chemicals | Propargyloxyacetonitrile derivatives,their preparation and fungicidal and herbicidal compositions containing them |
| US4616004A (en) | 1984-09-27 | 1986-10-07 | Chevron Research Company | 1-iodopropargyl-3,4-disubstituted-Δ2 -1,2,4-triazolidin-5-one fungicides |
| DE3510203A1 (en) | 1985-03-21 | 1986-09-25 | Bayer Ag, 5090 Leverkusen | NEW IODOPROPARGYL ETHER, A METHOD FOR THE PRODUCTION AND THEIR USE |
| DE3827721A1 (en) * | 1988-08-16 | 1990-02-22 | Ruetgerswerke Ag | WOOD PRESERVATIVES AND THEIR USE |
| US4945109A (en) | 1988-08-24 | 1990-07-31 | Buckman Laboratories International, Inc. | Ester of carbamic acid useful as a microbicide and a preservative |
| US4950685A (en) * | 1988-12-20 | 1990-08-21 | Kop-Coat, Inc. | Wood preservatives |
| DE4228352A1 (en) | 1992-02-19 | 1993-08-26 | Ruetgerswerke Ag | CHROME-FREE WOOD PRESERVATIVE |
| DE19680858D2 (en) * | 1995-09-29 | 1999-01-28 | Remmers Bauchemie Gmbh | Wood preservative |
| NZ507060A (en) * | 2000-09-20 | 2003-08-29 | Osmose New Zealand | Wood preservation compositions and procedures |
| EP1363497A1 (en) * | 2001-03-01 | 2003-11-26 | Lonza Inc. | Combination of an iodopropynyl derivative with a ketone acid or its salt and/or with an aromatic carboxylic acid or its salt |
| WO2005027635A1 (en) * | 2003-09-19 | 2005-03-31 | Arch Chemicals, Inc. | Stabilized halopropynyl compositions as preservatives |
| DE102004036918A1 (en) * | 2004-07-29 | 2007-02-08 | Georg-August-Universität Göttingen | Protective agent and remuneration for wood |
| US7993756B2 (en) * | 2005-05-04 | 2011-08-09 | Viance, Llc | Long-chain quaternary ammonium compounds as wood treatment agents |
| GB2438404A (en) * | 2006-05-24 | 2007-11-28 | Arch Timber Protection Ltd | Preserving wood with an amine oxide, an azole and a specified amine or quaternary ammonium compound, in synergistic proportions |
| US20100003345A1 (en) * | 2008-07-02 | 2010-01-07 | Kamlesh Gaglani | Synergistic antimicrobial mixtures |
| EP3085505A1 (en) * | 2015-04-24 | 2016-10-26 | RÜTGERS Organics GmbH | A composition comprising an active ingredient composition and an additive composition for penetrating a timber |
| US10119034B2 (en) * | 2015-10-09 | 2018-11-06 | Ziqiang Lu | Wood preservation products protected with a durable coating system |
| CN106217580A (en) * | 2016-08-23 | 2016-12-14 | 宁波大诚和电子有限公司 | A kind of improved portable audio amplifier |
| CN110113942A (en) * | 2016-11-07 | 2019-08-09 | 朱比兰特生命科学有限公司 | Synergistic antimicrobial compositions |
| US20240196901A1 (en) * | 2021-03-19 | 2024-06-20 | Arxada, LLC | Zinc and Boron Containing Enhanced Wood Preservative |
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| BR112022001840A2 (en) | 2022-06-21 |
| KR20220044326A (en) | 2022-04-07 |
| AU2020327938A1 (en) | 2022-02-24 |
| WO2021030202A1 (en) | 2021-02-18 |
| CN114206112B (en) | 2024-04-12 |
| JP2022543694A (en) | 2022-10-13 |
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