Wood preservatives

Details Wood preservatives Wood preservatives

1998-11-03

2002-08-27

Pak, John (Department: 1616)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C514S075000, C514S500000, C514S642000, C514S643000, C514S667000, C514S669000, C424S630000, C424S632000, C424S633000, C424S634000, C424S635000, C424S637000, C424S638000, C424SDIG001, C106S018320

Reexamination Certificate

active

06441016

ABSTRACT:

Wood preservatives based on inorganic copper compounds with alkanolamines as complexing agents are known (European Patent 89,958). Despite high copper contents, the activity of these agents against wood-destroying
Basidiomycetes
is insufficient in comparison with known copper- and chromate-containing salts having a comparable copper content.
It has now been found that wood preservatives based on copper compounds and alkanolamines, which contain a triazole compound and an emulsifier or which contain a phosphonium compound, have very good activity against wood-destroying
Basidiomycetes.
The present invention relates to mixtures which contain a triazole compound and an emulsifier, to mixtures which contain a phosphonium compound and to mixtures which contain a triazole compound, an emulsifier and a phosphonium compound.
In spite of the content of copper compounds in the wood preservative, on dilution with water the triazole compounds form a clear emulsion. The advantage of the novel agents is that triazole compounds which are insoluble in water are present in the novel agents in the the form of aqueous emulsions or clear aqueous concentrates. Clear aqueous liquids are formed on dilution with water.
Homogeneous concentrates can be obtained by adding small amounts of organic solvents to the wood preservative, for example alcohols (ethanol or isopropanol), glycols (ethylene glycol or propylene glycol), glycol ethers (ethylene glycol monomethyl ether or ethylene glycol monoethyl ether), glycol ether esters (butylglycol acetate), dimethylformamide or N-methyl-pyrrolidone. The solvents additionally act as solubilizers for the triazoles. With the additional use of arylcarboxylic acids, cycloalkylcarboxylic acids or aliphatic C
5
-C
20
-mono- or dicarboxylic acids or corresponding amine, alkali metal or copper salts, however, the use of solvents can be reduced to a minimum for obtaining homogeneous concentrates.
The copper compounds can be used as water-soluble or water-insoluble compounds, for example copper sulfate, copper acetate, copper hydroxide, copper oxide, copper borate, copper fluoride or basic copper carbonate.
An alkanolamine is, in particular, monoethanolamine; the use of other alkanolamines, for example isopropanolamine, 1,1- or 1,2-diaminoethanol, aminoethylethanolamine, diethanolamine, triethanolamine or methylethanolamine, is possible.
The amount of added alkanolamines is advantageously such that a pH of 7 or more, preferably from 8.5 to 10.5, is established in the dilute aqueous impregnating solution. The amount of amines should be sufficient for complexing the copper (1 g atom of copper requires about 4 mol equivalents of amine).
A triazole compound is, for example, 1-(2-(2,4-dichlorophenyl)-4-methyl-1,3-dioxolan-2-yl-methyl)-1H-1,2,4-triazole, 1-(2-(2,4-dichlorophenyl)-1,3-dioxolan-2-ylmethyl)-1H-1,2,4-triazole (azaconazole), 1-(2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-yl-methyl)-1H-1,2,4-triazole, 1-(2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl-methyl)-1H-1,2,4-triazole (propiconazole), 1-(2-(2,4-dichlorophenyl)-4-phenyl-1,3-dioxolan-2-yl-methyl)-1H-1,2,4-triazole or &agr;-tert-butyl-a-(p-chlorophenylethyl)-H-1,2,4-triazole-1-ethanol (tebuconazole).
An emulsifier is, for example, an anionic, cationic or nonionic emulsifier or a mixture thereof. Nonionic emulsifiers are, for example, adducts of ethylene oxide (EO) or propylene oxide or mixtures thereof with organic hydroxy compounds, for example alkylphenols, fatty acids, fatty alcohols and mixtures thereof. Examples of suitable cationic emulsifiers are quaternary ammonium compounds and/or salts of fatty amines (for example dimethyl-(C
12
-C
14
)-alkylamines).
A quaternary ammonium compound is, for example, a compound of the general formula R
1
R
2
R
3
R
4N
+
Z
−
, where R
1
is alkyl of 8 to 20 carbon atoms, in particular alkyl of 12 to 20 carbon atoms or benzyl which is unsubstituted or substituted by C
1
-C
20
-alkyl or halogen, R
2
is C
1
-C
6
-alkyl, C
3
-C
9
-alkoxyalkyl or polymeric ethylene oxide (EO) or propylene oxide (PO) where the number of EO or PO units n is from 2 to 50, R
3
is C
1
-C
6
-alkyl, C
3
- or C
4
-alkoxy or polymeric ethylene oxide (EO) or propylene oxide (PO) where the number of EO or PO units n is from 2 to 50 and R
4
is C
1
-C
20
-alkyl, or two of the radicals R
1
to R
4
, together with the nitrogen atom, form a heterocyclic radical which contains 4 or 5 carbon atoms and one, two or three double bonds, the carbon atoms being unsubstituted or substituted by C
1
-C
4
-alkyl or halogen, and Z is an acid radical, eg. halide.
Particularly suitable phosphonium compounds are compounds of the formula
R
1
3
R
2
P
+
Y
−
where R
1
is alkyl of 1 to 6 carbon atoms, hydroxyalkyl of 1 to 6 carbon atoms or phenyl, R
2
is alkyl of 8 to 18 carbon atoms and Y is an acid radical, in particular a halide anion.
R
1
and R
2
are preferably straight-chain.
The quaternary phosphonium compounds may be present individually or as mixtures in the novel concentrates. Examples of such phosphonium compounds are trimethyl-n-dodecylphosphonium chloride, triethyl-n-decylphosphonium bromide, tri-n-propyl-n-tetradecylphosphonium chloride, trimethylol-n-hexadecylphosphonium chloride, tri-n-butyl-n-tetradecylphosphonium chloride, tri-n-butyl-n-dodecylphosphonium bromide, tri-n-butyl-n-decylphosphonium chloride, tri-n-butyl-n-hexadecylphosphonium bromide, tri-n-hexyl-n-decylphosphonium chloride, triphenyl-n-dodecylphosphonium chloride, triphenyl-n-tetradecylphosphonium bromide and triphenyl-n-octadecylphosphonium chloride.
Aliphatic carboxylic acids can be added to improve the homogeneity of the concentrates. Examples of such acids are propionic acid, hexanoic acid, heptanoic acid, branched carboxylic acids, eg. 2-ethylenehexanoic acid or isooctanoic acid, neocarboxylic acids, aliphatic dicarboxylic acids, eg. sebacic acid, cycloalkylcarboxylic acids, eg. cyclohexanoic acid, and arylcarboxylic acids, eg. benzoic acid or 3- or 4-hydroxybenzoic acid.
When the abovementioned acids are used, it is advantageous in some cases to improve the penetration of the wood preservative in large scale industrial processes by adding complex-forming, polymeric nitrogen compounds, eg. polyethyleneimines.
Polyethyleneimines (PEI, polymin) are known and are formed by polymerization of 1,2-ethyleneimine. They contain the nitrogen in primary (terminal group), secondary or tertiary (branching) form. Polyethyleneimines where n is greater than 10 are suitable; very good results are obtained when PEI having a degree of polymerization n between 50 and 1,000 are used.
The wood preservatives may, if required, contain further compounds, for example compounds having a fungicidal anion, such as a boron compound (for example alkali metal borate, aminoborate, boric acid or boric ester) and fluorides (for example potassium fluoride and/or salts of fluoboric acid and/or fluophosphoric acid and/or difluophosphoric acid).
The action spectrum of the novel wood preservatives can, if required, be improved by adding further active ingredients. Examples of suitable compounds are N-organodiazeniumdioxy compounds, organotin compounds, in particular tributyltin (TBT) compounds and isothiazoline compounds of the following formula
where R
1
is hydrogen, an alkyl, alkenyl or alkynyl radical of 1 to 18 carbon atoms, cycloalkyl having a C
3
-C
6
-ring and not more than 12 carbon atoms or an aralkyl or aryl radical of not more than 19 carbon atoms and R
2
and R
3
independently of one another are hydrogen, halogen or C
1
-C
4
-alkyl, or R
2
and R
3
are part of an aromatic radical.
It is also possible to add further fungicides or insecticides, for example in emulsified form, such as N-tridecyl-2,6-dimethylmorpholine (tridemorph) and/or 4-(3-para-tert-butylphenyl)-2-methyl-propyl-2,6-cis-dimethylmorpholine (fenpropimorph) and/or chlorinated phenols tetrachloroisophthalodinitrile N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide N-dimethyl-N′-phenyl-(N-fluoromethylthio)-sulfamide N,N-dimethyl-N′-toluyl-(N-fluoromethylt

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