EP4009791A1 - Composition synergique de conservation du bois comprenant de la bétaïne polymère et du carbamate - Google Patents

Composition synergique de conservation du bois comprenant de la bétaïne polymère et du carbamate

Info

Publication number
EP4009791A1
EP4009791A1 EP20760709.4A EP20760709A EP4009791A1 EP 4009791 A1 EP4009791 A1 EP 4009791A1 EP 20760709 A EP20760709 A EP 20760709A EP 4009791 A1 EP4009791 A1 EP 4009791A1
Authority
EP
European Patent Office
Prior art keywords
composition
wood
ipbc
weight
polymeric
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.)
Withdrawn
Application number
EP20760709.4A
Other languages
German (de)
English (en)
Inventor
Min Chen
Jake Zachary JACOBS
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.)
Troy Corp
Original Assignee
Troy Corp
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 Troy Corp filed Critical Troy Corp
Publication of EP4009791A1 publication Critical patent/EP4009791A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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

Definitions

  • the present invention pertains to synergistic compositions suitable for use in the treatment and preservation of wood and wood products.
  • the antimicrobial compositions of this invention include wood preservative compositions comprising a polymeric betaine and an iodopropynyl compound. These 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.
  • antimicrobial materials included halogenated compounds, organometallic compounds, quaternary ammonium compounds, phenolics, metallic salts, heterocyclic amines, formaldehyde adducts, organosulfur compounds, and the like.
  • No single organic antimicrobial compound is able to provide protection against all microorganisms and is suitable for all applications.
  • other limitations may restrict the usefulness of certain antimicrobials. For example the stability, physical properties, toxicological profile, regulatory considerations, economic considerations or environmental concerns may 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.
  • a judicious choice of combinations may provide a way to maximize benefits while at the same time minimize problems.
  • a combination wherein the antimicrobial activity is enhanced while the less desirable properties are suppressed or reduced can provide a superior product.
  • the task is to find 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 will not have any strong adverse effects on health or the environment.
  • 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 controlling mold and/or sapstain on wood or wood products by application of an effective amount of such compositions to the wood or wood product substrate.
  • iodopropynyl compounds such as 3-iodo-2- propynyl butyl carbamate (IPBC) are combined with polymeric betaines such as didecyl bis(hydroxyethyl) ammonium borate (DPAB), they form wood preservative compositions that are surprisingly more effective against microorganisms that produce mold and/or sapstain on wood or wood products than either single component alone.
  • polymeric betaines and iodopropynyl compounds complement one another in a way that could not be anticipated.
  • the polymeric betaines and iodopropynl compound show synergistic activity. This unexpected synergistic activity offers a number of advantages in the preservation of wood and wood products.
  • This invention relates to the synergistic wood preservative composition
  • polymeric 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 produce mold and sapstain.
  • DPAB didecyl bis(hydroxyethyl) ammonium borate
  • 3-iodo-2-propynyl butyl carbamate having the properties of providing effective and broader control of microorganisms that produce mold and sapstain.
  • Suitable polymeric betaines are described in, for example, U.S. Patent No. 5,304,237, the entire contents of which are incorporated herein by reference.
  • the structural formula of DPAB is:
  • the antisapstain compositions of the invention can be prepared as solutions or emulsions by conventional means by using water or organic liquids as a solvent.
  • a preferred form
  • the quantity and ratio of polymeric betaine and IPBC will depend upon the specific application.
  • the wood preservative composition will contain from about 1 to 100 parts by weight polymeric betaine per about 1 to 100 parts by weight IPBC. More preferably, the composition will contain about 1 to 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 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.
  • a particularly preferred ratio of polymeric betaine to IPBC is from 5: 1 to 10: 1 parts by weight, i.e., about 5 to 10 parts by weight polymeric betaine per part by weight IPBC.
  • Other preferred ratios of polymeric 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, 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
  • the preservative composition 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 weight solvent.
  • the composition may comprise more than 80 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 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 solvents include water and/or organic solvents, including aromatic organic solvents, polar and non-polar organic solvents, and aliphatic organic solvents.
  • the concentrate is generally diluted about 10 to 200 times to working solution strength by the addition of water (or another solvent).
  • the diluted solution or emulsion can be applied to wood by conventional treating methods such as immersion, brush, spray, flooding, or pressure.
  • 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 complimentary activity that allows one to use less biocide in combination to achieve a desired effect at levels that cannot be achieved with any of the individual ingredients.
  • halopropynyl compounds that can be used in accordance with the present invention, for the most part, are well known and can be generally identified by the following structure:
  • YC C-CH 2 X
  • X can be (1) oxygen that is part of an organic functional group; (2) nitrogen that is part of an organic functional group; (3) sulfur that is part of an organic functional group; or (4) carbon 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 group.
  • the functional group of which nitrogen is a part is preferably an amine, an amide, or a carbamate group.
  • the functional group of which sulfur is a part is preferably a thiol, a thiane, a sulfone, or a sulfoxide group.
  • the organic functional group of which carbon is a part is preferably an ester, a carbamate or an alkyl group.
  • Examples of compounds that may be used as the halopropynyl compound of this invention are especially the active iodopropynyl derivatives some of which are reported in U.S. Pat. Nos. 3,923,870; 4,259,350; 4,592,773; 4,616,004; 4,719,227; and 4,945,109.
  • iodopropynyl derivatives include compounds derived from propynyl or iodopropynyl alcohols such as esters, acetals, carbamates and carbonates and further include the iodopropynyl derivatives of pyrimidines, thiazolinones, tetrazoles, triazinones, sulfamides, benzothiazoles, ammonium salts, carboxamides, and ureas.
  • R may have one to three linkages corresponding to n and is selected from the group consisting of hydrogen, substituted and unsubstituted alkyl groups having from 1 to 20 carbon atoms, substituted and unsubstituted aryl, alkylaryl, and aralkyl of from 6 to 20 carbon atoms or cycloalkyl and cycloalkenyl groups of from 3 to 10 carbon atoms, and m and n are independently integers from 1 to 3, i.e., they are not necessarily the same.
  • Suitable R substituents include alkyls such as methyl, ethyl, propyl, n-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, and octadecyl; cycloalkyls such as cyclohexyl; aryls, alkaryls and aralkyls such as phenyl, benzyl, tolyl, and cumyl; halogenated alkyls and aryls, such as chlorobutyl and chlorophenyl; and alkoxy aryls such as ethoxyphenyl and the like.
  • iodopropynyl carbamates as 3-iodo-2-propynyl propyl carbamate, 3-iodo-2-propynyl butyl carbamate, 3-iodo-2-propynyl hexyl carbamate, 3-iodo-2-propynyl cyclohexyl carbamate, 3-iodo-2-propynyl phenyl carbamate, and mixtures thereof.
  • compositions of the present invention will generally be formulated by mixing or dispersing the 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 the biocidal compositions include the protection of wood, wood products, fresh sawn timber, and the like.
  • the compositions of this invention may be provided as liquid mixtures such as dispersions, emulsions, microemulsions, or in any other suitable product form that is desirable or most useful.
  • the composition also will likely be provided with adjuvants conventionally employed in compositions intended for such applications such as organic binding agents, additional fungicides, auxiliary solvents, processing additives, fixatives, plasticizers, UV-stabilizers or stability enhancers, water soluble or water insoluble dyes, color pigments, siccatives, corrosion inhibitors, antisettlement agents, anti-skinning agents and the like.
  • adjuvants conventionally employed in compositions intended for such applications such as organic binding agents, additional fungicides, auxiliary solvents, processing additives, fixatives, plasticizers, UV-stabilizers or stability enhancers, water soluble or water insoluble dyes, color pigments, siccatives, corrosion inhibitors, antisettlement agents, anti-skinning agents and the like.
  • substrates are protected from contamination by microorganisms simply by treating said substrate with a composition of the present invention. Such treating may involve mixing the composition with the substrate, coating or otherwise contacting the substrate with the composition and the like.
  • IPBC solvent solution Polyphase AF-1, Troy Chemical Corporation, Newark, NJ
  • Suspension strength was determined via hemocytometer then adjusted to lxlO 6 spores/mL with sterile deionized water.
  • MIC Minimum inhibitory concentration
  • Table 4 The growth of Trichoderma oseudokoninaii (ATCC# 268011 in 96-well plates containing selected concentrations of DPAB. IPBC and their mixture. The values stated wells 1 through 12 are in ppm active.
  • 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

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • General Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (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

L'invention concerne une composition synergique de conservation du bois comprenant une bétaïne polymère et du carbamate de 3-iodo-2-propynyle butyle (IPBC). L'invention concerne également un procédé de lutte contre des micro-organismes qui produisent des moisissures et/ou des taches de sève sur du bois ou des produits en bois par application, sur du bois ou un produit en bois, de la composition synergique de conservation du bois pour lutter contre les micro-organismes.
EP20760709.4A 2019-08-09 2020-08-07 Composition synergique de conservation du bois comprenant de la bétaïne polymère et du carbamate Withdrawn EP4009791A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201962884738P 2019-08-09 2019-08-09
PCT/US2020/045452 WO2021030202A1 (fr) 2019-08-09 2020-08-07 Composition synergique de conservation du bois comprenant de la bétaïne polymère et du carbamate

Publications (1)

Publication Number Publication Date
EP4009791A1 true EP4009791A1 (fr) 2022-06-15

Family

ID=72179257

Family Applications (1)

Application Number Title Priority Date Filing Date
EP20760709.4A Withdrawn EP4009791A1 (fr) 2019-08-09 2020-08-07 Composition synergique de conservation du bois comprenant de la bétaïne polymère et du carbamate

Country Status (8)

Country Link
EP (1) EP4009791A1 (fr)
JP (1) JP2022543694A (fr)
KR (1) KR20220044326A (fr)
CN (1) CN114206112B (fr)
AU (1) AU2020327938A1 (fr)
BR (1) BR112022001840A2 (fr)
CA (1) CA3149341C (fr)
WO (1) WO2021030202A1 (fr)

Family Cites Families (22)

* Cited by examiner, † Cited by third party
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US3923870A (en) * 1973-07-11 1975-12-02 Troy Chemical Corp Urethanes of 1-halogen substituted alkynes
US4259350A (en) 1978-03-15 1981-03-31 Sankyo Company Limited 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 (de) 1985-03-21 1986-09-25 Bayer Ag, 5090 Leverkusen Neue iodpropargylether, ein verfahren zu ihrer herstellung und ihre verwendung
DE3827721A1 (de) * 1988-08-16 1990-02-22 Ruetgerswerke Ag Mittel zum konservieren von holz und ihre verwendung
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 (de) 1992-02-19 1993-08-26 Ruetgerswerke Ag Chromfreies holzschutzmittel
DE19680858D2 (de) * 1995-09-29 1999-01-28 Remmers Bauchemie Gmbh Holzschutzmittel
NZ507060A (en) * 2000-09-20 2003-08-29 Osmose New Zealand Wood preservation compositions and procedures
CA2439640A1 (fr) * 2001-03-01 2002-09-12 Lonza Inc. Combinaison d'un derive d'iodopropynyle et d'un acide cetonique ou de son sel et/ou d'un acide carboxylique aromatique ou de son sel
CA2539185A1 (fr) * 2003-09-19 2005-03-31 Arch Chemicals, Inc. Compositions d'halopropynyle stabilisees en tant qu'agents de conservation
DE102004036918A1 (de) * 2004-07-29 2007-02-08 Georg-August-Universität Göttingen Schutzmittel und Vergütung für Holz
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 (fr) * 2015-04-24 2016-10-26 RÜTGERS Organics GmbH Composition comprenant une préparation de principe actif et une composition d'additif pour pénétrer un bois
US10119034B2 (en) * 2015-10-09 2018-11-06 Ziqiang Lu Wood preservation products protected with a durable coating system
CN106217580A (zh) * 2016-08-23 2016-12-14 宁波大诚和电子有限公司 一种改进型便携音箱
EP3534708A1 (fr) * 2016-11-07 2019-09-11 Jubilant Life Sciences Limited Compositions antimicrobiennes synergiques
EP4291377A4 (fr) * 2021-03-19 2025-02-12 Arxada, LLC Agent de conservation du bois amélioré contenant du zinc et du bore

Also Published As

Publication number Publication date
CA3149341C (fr) 2024-03-05
WO2021030202A1 (fr) 2021-02-18
BR112022001840A2 (pt) 2022-06-21
JP2022543694A (ja) 2022-10-13
KR20220044326A (ko) 2022-04-07
CA3149341A1 (fr) 2021-02-18
CN114206112B (zh) 2024-04-12
CN114206112A (zh) 2022-03-18
AU2020327938A1 (en) 2022-02-24

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