Amine oxide/iodine containing blends for wood preservation

Details Amine oxide/iodine containing blends for wood preservation Amine oxide/iodine containing blends for wood preservation

2000-05-24

2002-04-23

Green, Anthony (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Contains fireproofing or biocidal agent

C106S002000, C106S018350, C514S228800, C514S231200, C514S075000, C514S478000, C514S479000, C514S644000, C514S672000

Reexamination Certificate

active

06375727

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to wood preservative and waterproofing compositions containing an amine oxide and an iodine containing biocide.
BACKGROUND OF THE INVENTION
Mixtures of didecyldimethylammonium chloride (DDAC) and iodine containing biocides such as iodopropynylbutylcarbamate (IPBC), are currently used for treating wood to prevent the growth of stain causing fungi (see, e.g., U.S. Pat. No. 4,950,685). IPBC is known to be effective against fungi that cause structural and cosmetic damage to wood.
These mixtures are often distributed as concentrates. When diluted, the solutions frequently are characterized by poor phase and color stability, the IPBC often coming out of solution within a day or two after preparation. These solution also have low corrosion resistance. Furthermore, DDAC and IPBC compositions containing iron stain inhibitors typically have a low pH, making them less desirable for use in mills and other factories. A firer disadvantage of many of the prior art wood preservative compositions is that they contain halides, which are considered environmentally unfriendly.
Therefore, there is a need for iodine containing biocide compositions which have improved phase and color stability and corrosion resistance, and are able to form compositions containing iron stain inhibitors at higher pH.
SUMMARY OF THE INVENTION
Applicants have discovered that amine oxides enhance the performance of iodine-containing biocides as wood preservatives and provide waterproofing properties. The present invention provides a composition comprising an amine oxide and an iodine-containing biocide, particularly iodopropynyl butyl carbamate.
Another embodiment of the present invention is a method for preserving and/or waterproofing a wood substrate by impregnating the wood substrate with the composition.
Yet another embodiment is an article comprising a wood substrate treated with the composition of the present invention.
The composition of the invention has improved phase stability over prior art compositions and high resistance to color formation. The composition of the invention also has low corrosivity to metal components, including, but not limited to, steel components, such as those used in wood treatment systems. Compositions of the present invention which include iron stain inhibitors generally have higher pH than prior art iodine containing biocide containing compositions, allowing for safer handling of such compositions. Additionally, the amine oxide in the composition may impart waterproofing properties to the wood. Further, the composition of the present invention may be advantageously free of halide ions.
DETAILED DESCRIPTION OF THE INVENTION
Examples of compounds which may be used as the iodopropynyl component of the invention are the fungicidally active iodoalkynyl derivatives. These include compounds derived from propyne or iodopropynyl alcohols, such as the esters, ethers, acetals, carbamates and carbonates and the iodopropynyl derivatives of pyrimidines, triazolinones, tetrazoles, triazinones, sulfamides, benzothiazoles, ammonium salts, carboxamides, hydroxamates, and ureas.
Preferred iodine containing biocides include 3-iodo-2 propynyl derivatives such as 3-iodo-2-propynyl butyl carbamate, 3-iodo-2-propynyl succinate and p-chlorophenyl-3-iodopropynyl formal; an iodo sulfone derivative, or triiodoallyl alcohol.
The iodopropynyl carbamate compounds, included within the broadly useful class of compounds, have the generic formula:
wherein R is selected from the group consisting of hydrogen, and substituted and unsubstituted alkyl, aryl, and alkylaryl groups having from 1 to 20 carbon atoms; and q and z are independent integers from 1 to 3.
The iodopropynyl ester compounds are included within the broadly useful class of compounds having the generic formulas:
wherein:
R
1
and R
2
are defined as R
3
and R
4
below or are joined to form a cycloalkyl, cycloalkenyl, aromatic or a heterocyclic ring containing an oxygen, nitrogen or sulfur atom or an alkoxy, amino, carboxyl, halo, hydroxyl, keto or a thiocarboxyl-substituted derivative thereof;
R
3
and R
4
are independently selected from (A) hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, a heterocyclic ring containing an oxygen, nitrogen or sulfur atom, alkoxy, amino, carboxyl, halo, hydroxyl, keto or a thiocarboxyl and (B) substituted derivatives of the alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl and the heterocyclic ring wherein the substitutions are alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, alkoxy, amino, carboxyl, halo, hydroxyl, keto or a thiocarboxyl; y is 0 to 16; W may be a single bond, oxygen, NR
5
, or (CR
6
R
7
)
p
, wherein R
5
is hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl or a heterocyclic ring containing an oxygen, nitrogen or sulfur atom or a substituted derivative of alkyl, cycloalkyl, alkenyl, cycloalkenyl or aryl groups wherein the substitutions are alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, alkoxy, amino, carboxyl, halo, hydroxyl, keto, or a thiocarboxyl wherein R
6
and R
7
are defined as R
3
and R
4
above; and p is an integer from 1 to 12. The above definition of R
5
includes, among other things, an aminoalkyl group.
The heterocyclic rings referred to in the above definitions may contain from 5 to 8 members, the alkyl or cycloalkyl groups from 1 to 18 atoms, the alkenyl or cycloalkenyl groups from 2 to 18 carbon atoms, and the aryl groups from 6 to 10 members. X is hydrogen or a salt-forming cation such as an alkali metal, an alkaline earth metal, ammonium, tertiary ammonium, a quaternary ammonium, a biguanide or a polybiguanide.
In formula III, when R
1
and R
2
are hydrogen, the compound is a maleate. When R
1
and R
2
are joined together to form part of a six membered aromatic ring the compound is a phthalate. In formula II, when R
1
, R
2
, R
3
, and R
4
are hydrogen and W is a single bond, the compound is a succinate. When R
1
, R
2
, R
3
and R
4
are hydrogen and W is an oxygen, the compound is a diglycolate. Other compounds include the mono-iodopropynyl esters of anhydrides such as ethylenediamine tetraacetic dianhydride, 3,3-dimethylglutaric anhydride, S-acetylmercaptosuccinic anhydride, dichloromaleic anhydride, 2-dodecen-1-yl succinic anhydride and cis-5-norbornene-endo-2,3-dicarboxylic anhydride. Where hydrophilicity is desired, the sodium salts may be used because of their extremely high water solubility. Preferred carboxylic acid anhydrides include succinic, itaconic, phthalic, tetrachlorophthalic, and diglycolic anhydride. Such compounds are defined in U.S. Pat. No. 4,844,891 and 5,073,570.
More preferably the iodine containing biocide is 3-iodo-2-propynyl butyl carbamate (IPBC). The IPBC may be any grade of IPBC including, but not limited to, an essentially pure commercial grade IPBC in solid form and a commercially available 40% grade in a solvent.
The iodopropynyl compounds are also included within the class of compounds having the generic formula:
I—C≡C—(CH
2
O
2
)
2
—R
8
wherein R
8
is benzyl or benzyl substituted with a methyl, methoxy, carboxyl, halogen or nitro group; preferably the compound is p-chlorophenyl-3- iodopropynyl formal.
The amine oxide may be a trialkylamine oxide; an alkylcyclicamine oxide; a dialkylpiperazine di-N-oxide; an alkyldi(poly(oxyalkylene))amine oxide; a dialkylbenzylamine oxide; a fatty acylamidopropyldimethylamine oxide; a diamine oxide; a triamine oxide; and any combination of any of the foregoing.
Preferred trialkylamine oxides have the formula R
9
R
10
R
11
N→O, where R
9
is a linear, branched, cyclic or any combination thereof C
6
to C
40
saturated or unsaturated group; and R
10
and R
11
independently are linear, branched, or any combination thereof C
1
to C
40
saturated or unsaturated groups. R
9
, R
10
, and R
11
independently may be alkyl, alkenyl, or alkynyl groups; or may be replaced by other short chain alkyl or substituted alkyl groups, such as ethyl and hydroxyethyl. More preferably, R
9
is a linear, branched, cyclic or any combination thereof C
8
to C
22
s

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