EP4009791A1 - Synergistic wood preservative composition comprising polymeric betaine and carbamate - Google Patents
Synergistic wood preservative composition comprising polymeric betaine and carbamateInfo
- 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- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 53
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 229960003237 betaine Drugs 0.000 title claims abstract description 28
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 title claims abstract description 26
- 230000002195 synergetic effect Effects 0.000 title claims abstract description 11
- 239000003171 wood protecting agent Substances 0.000 title description 9
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 title description 5
- 229940099451 3-iodo-2-propynylbutylcarbamate Drugs 0.000 claims abstract description 31
- WYVVKGNFXHOCQV-UHFFFAOYSA-N 3-iodoprop-2-yn-1-yl butylcarbamate Chemical compound CCCCNC(=O)OCC#CI WYVVKGNFXHOCQV-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000002023 wood Substances 0.000 claims abstract description 31
- 244000005700 microbiome Species 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 9
- 238000004321 preservation Methods 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims description 17
- 239000000243 solution Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000000839 emulsion Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- LKZVYRAXTFZCMF-UHFFFAOYSA-N B([O-])([O-])[O-].C(CCCCCCCCC)[N+](CCO)(CCO)CCCCCCCCCC.C(CCCCCCCCC)[N+](CCCCCCCCCC)(CCO)CCO.C(CCCCCCCCC)[N+](CCCCCCCCCC)(CCO)CCO Chemical compound B([O-])([O-])[O-].C(CCCCCCCCC)[N+](CCO)(CCO)CCCCCCCCCC.C(CCCCCCCCC)[N+](CCCCCCCCCC)(CCO)CCO.C(CCCCCCCCC)[N+](CCCCCCCCCC)(CCO)CCO LKZVYRAXTFZCMF-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 238000007654 immersion Methods 0.000 claims description 2
- 239000007921 spray Substances 0.000 claims description 2
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 239000003849 aromatic solvent Substances 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- -1 iodopropynyl compound Chemical class 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 230000002538 fungal effect Effects 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 230000000845 anti-microbial effect Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
- 230000002335 preservative effect Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 241000223678 Aureobasidium pullulans Species 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- IABBAGAOMDWOCW-UHFFFAOYSA-N Nicametate citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.CCN(CC)CCOC(=O)C1=CC=CN=C1 IABBAGAOMDWOCW-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 241001136494 Talaromyces funiculosus Species 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 230000036512 infertility Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
- HPGGRRWTQXPMHJ-UHFFFAOYSA-N 3-iodoprop-1-ynyl carbamate Chemical class NC(=O)OC#CCI HPGGRRWTQXPMHJ-UHFFFAOYSA-N 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical class O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
- 241000223259 Trichoderma Species 0.000 description 1
- 241001304120 Trichoderma pseudokoningii Species 0.000 description 1
- 241001557886 Trichoderma sp. Species 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000004171 alkoxy aryl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 238000002827 antifungal susceptibility testing Methods 0.000 description 1
- 239000002635 aromatic organic solvent Substances 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 229920005556 chlorobutyl Polymers 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000019645 odor Nutrition 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000583 toxicological profile Toxicity 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000012224 working solution Substances 0.000 description 1
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
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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
SYNERGISTIC WOOD PRESERVATIVE COMPOSITION COMPRISING POLYMERIC BETAINE
AND CARBAMATE
CROSS-REFERENCE TO RELATED APPLICATIONS
The present application claims priority to U.S. Provisional Patent Application No. 62/884,738, filed August 9, 2019, entitled "SYNERGISTIC WOOD PRESERVATIVE COMPOSITION COMPRISING POLYMERIC BETAINE AND CARBAMATE" the contents of which are incorporated herein by reference in their entirety.
BACKGROUND OF THE INVENTION
1. Field of the Invention
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.
2. Description of the Background
Substrates of all types, when exposed to common environmental conditions, are prone to attack, spoilage and various kinds of destruction by a variety of species of microorganisms including fungi, yeast, 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 destruction caused by such microorganisms. Materials that need protection against such microorganisms include, for example, wood and wood products, which are prone to degradation by the action of objectionable microorganisms. Such degradation may produce, inter alia, deterioration, discoloration, the 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 degrees, are effective in retarding or preventing the growth of, and accompanying destruction caused by, such microorganisms in a variety of circumstances. Such 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. In addition to such limitations concerning efficacy, 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. Ideally, 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.
SUMMARY OF THE INVENTION
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.
DETAILED DESCRIPTION OF THE INVENTION
It has been found that when 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. 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 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 comprising of 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. 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 is to combine a water solution of polymeric betaine and an organic solvent solution of IPBC. The process conditions for 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. Generally, 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 7:9, 9:8 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 combined with the lower limits of the other ranges, and vice-versa, in accordance with other aspects of the invention.
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 weight solvent. According to another aspect of the invention 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.
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 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.
The 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-CH2X wherein Y is halogen, and 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. These 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.
The preferred and most widely used among these compounds is the halopropynyl carbamate, 3-iodo-2-propynyl butyl carbamate. These compounds are included within the useful class of compounds having the generic formula:
wherein 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.
Particularly preferred are formulations of such halopropynyl carbamates where m is 1 and n is 1 and which have the following formula:
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.
Especially preferred are such 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.
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 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.
According to the present invention, 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.
The following example is presented to illustrate and explain the invention.
Unless otherwise indicated, all references to parts and percentages are based on weight.
Example 1
To show the efficacy of the composition of the invention on wood deteriorating microorganisms, the following solutions were prepared:
(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) was diluted in 9.83 g ethanol by stirring to form a concentrate containing 1% DPAB.
(B) 0.25 g of 40% IPBC solvent solution (Polyphase AF-1, Troy Chemical Corporation, Newark, NJ) was diluted in 9.75 g ethanol by stirring to form a concentrate containing 1% IPBC.
(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), 6.25 g of 40% IPBC solvent solution (Polyphase AF-1, Troy Chemical Corporation, Newark, NJ) and 22.74 g of ethanol were mixed and stirred. The resulting concentrate contained 25% polymeric betaine and 5% IPBC. The weight ratio of polymeric betaine to IPBC was 5: 1. 0.33 g of this IPBC/polymeric betaine concentrate was diluted in 9.67 g of ethanol to form a use-dilution containing about 0.83% DPAB and 0.17% IPBC.
Solutions prepared as described above were tested in 96-well plates for their ability to inhibit fungal growth. The solutions were tested according to the EUCAST methodology as described in Rodriguez-Tudela et a/. 2006 "Antifungal susceptibility testing in Aspergillus spp. according to EUCAST methodology.". The solutions were checked for inhibition against fungal organisms Aspergillus niger (ATCC# 6275), Aureobasidium pullulans (ATCC# 9348), Penicillium funiculosum (ATCC# 11797) and Trichoderma pseudokoningii (ATCC# 26801). This method is briefly described below:
(1) Prepared preservative test wells by adding 2 microliters of each 1% preservative solution formulation to 198 microliters of 2xRPMI-MOPS-2% Glucose in each column "1" in duplicate.
(2) Added 100 microliters of 2xRPMI-MOPS-2% Glucose to the remaining columns.
(3) Performed 2-fold dilutions down the columns to column "12".
(4) Prepared suspension of microorganisms from a 3-5 day old PDA slants by flooding slant with 1 mL deionized water and 0.1% Tween-20.
(5) Suspension strength was determined via hemocytometer then adjusted to lxlO6 spores/mL with sterile deionized water.
5 (6) Added 100 microliters of the microorganism suspension to all wells except for sterility (-) controls containing test media. The water used to prepare the fungal suspensions was added to sterility (-) control wells.
(7) The inoculated 96-well plates were incubated for 3 days at 35°C.
(8) After incubation, fungal growth was evaluated by visual growth in test wells.
10 Minimum inhibitory concentration (MIC) is recorded in ppm and defined as the lowest concentration of fungicide that produces no visual changes in turbidity in the test wells.
(9) The experiment is only considered valid if growth is observed in the positive (+) control wells and no growth is observed in the negative control wells.
The effectiveness on all four examined microorganisms is presented in Tables 1
15 to 4.
Table 3. The growth of Penicillium funiculosum (ATCC# 117971 in 96-well plates containing selected concentrations of DPAB. IPBC and their mixture.
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.
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:
(MCA'/MCA) + (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
These tests clearly demonstrate that the combination of polymeric betaine (DPAB) and IPBC provided significantly unexpectedly greater protection against the sapstain organism Aureobasidium pullulans and the mold organism Trichoderma sp.
5 than treatments of either of the two components taken alone.
While the invention has been particularly described in terms of specific embodiments, those skilled in the art will understand in view of the present disclosure that numerous variations and modifications upon the invention are now enabled, which variations and modifications are not to be regarded as a departure from the spirit and 10 scope of the invention. Accordingly, the invention is to be broadly construed and limited only by the scope and spirit of the following claims.
Claims
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962884738P | 2019-08-09 | 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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| Publication Number | Publication Date |
|---|---|
| EP4009791A1 true EP4009791A1 (en) | 2022-06-15 |
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| EP20760709.4A Withdrawn EP4009791A1 (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) |
| CA (1) | CA3149341C (en) |
| WO (1) | WO2021030202A1 (en) |
Family Cites Families (20)
| 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 |
| 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 (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 |
| JP4017665B2 (en) * | 1995-09-29 | 2007-12-05 | ローム・アンド・ハース・カンパニー | Wood preservatives |
| NZ507060A (en) * | 2000-09-20 | 2003-08-29 | Osmose New Zealand | Wood preservation compositions and procedures |
| CA2439640A1 (en) * | 2001-03-01 | 2002-09-12 | 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 |
| 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 |
| JP2024511719A (en) * | 2021-03-19 | 2024-03-15 | アークサーダ・リミテッド・ライアビリティ・カンパニー | Reinforced wood preservative containing zinc and boron |
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- 2020-08-07 JP JP2022507888A patent/JP2022543694A/en active Pending
- 2020-08-07 BR BR112022001840A patent/BR112022001840A2/en unknown
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- 2020-08-07 AU AU2020327938A patent/AU2020327938A1/en not_active Abandoned
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| CN114206112A (en) | 2022-03-18 |
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| JP2022543694A (en) | 2022-10-13 |
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