Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Reexamination Certificate
1998-02-27
2001-01-09
Qazi, Sabiha N. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
C514S514000, C514S642000, C514S643000, C514S515000, C514S315000, C514S358000, C514S428000, C514S183000, C514S210030, C514S212010, C424S405000
Reexamination Certificate
active
06172117
ABSTRACT:
BACKGROUND
1. Technical Field
This disclosure relates to preservatives, and particularly to biocidal preservative agents suitable for the preservation of wood, cotton, and other materials.
2. Background of the Art
Biocidal agents are often used to prevent the rotting and deterioration of various materials caused by bacteria, algae, fungus and mold. Such agents are especially needed for the preservation of wood, which is commonly used as a construction material.
Various formulations are available for the preservation of wood. Inorganic salts, particularly chromated copper arsenate, have often been used to treat wood. However, such salts pose a problem with respect to ground contamination as they leach from the wood.
As an alternative to the use of inorganic salts, organic compounds, optionally complexed with an inorganic metal such as copper, have also been used.
For example, U.S. Pat. No. 5,426,121 to Bell discloses wood preservatives which comprise a solution of a complex derived from copper and an alkoxylated diamine containing at least one fatty alkyl group.
U.S. Pat. No. 5,536,305 to Yu discloses a wood preservative composition consisting essentially of 4,5-dichloro-2-n-3-isothiazolone and a surfactant such as an anionic, cationic, or amphoteric surfactant.
Quaternary ammonium compounds are also known to be useful biocidal agents. However, wood treated with quaternary ammonium compounds tends to fail when used in applications with high decay hazards, such as in ground uses like posts, pilings and utility poles. Accordingly, it is desirable to develop quaternary ammonium compounds that may have greater biocidal activity.
SUMMARY OF THE INVENTION
Biocidal preservative compositions are provided herein. The preservative compositions comprise one or more compounds of the following formulas (I)-(III).
Thus, in one embodiment the preservative composition comprises a compound of the formula:
wherein X
−
is an anion and y can vary from 1 to 12, and R
1
, R
2
and R
3
can be the same or different and are independently selected from the group consisting of straight or branched chain aliphatic moieties of from about 1 to about 22 carbon atoms, benzyl moieties with or without substitutions, —(C
a
H
2a
O)
n
H wherein a is 2, 3, or 4 and n is from about 1 to about 20 and 2-hydroxyl-2-phenylethyl. Optionally, R
1
and R
2
with N
+
can form a heterocyclic moiety having from about 4 to about 10 carbon atoms.
In yet another embodiment the preservative composition comprises a compound of the formula:
wherein X
−
is an anion, R
4
is a straight or branched chain aliphatic moiety having from about 6 to about 22 carbon atoms; R
5
and R
6
can be the same or different and are independently selected from the group consisting of aliphatic moieties of from about 1 to about 22 carbon atoms, —(C
a
H
2a
O)
n
H wherein a is 2, 3, or 4 and n is from about 1 to about 20 and 2-hydroxyl-2-phenylethyl; Z is a bridging group of the formula —(C
a
H
2a
O)
n
—CHY)
x
— wherein a is from about 1 to about 4, n is from 0 to about 10, x is from about 1 to about 10 and Y is the same or different at each occurrence and is selected from the group consisting of hydrogen and hydroxyl groups; and R
7
is chosen from the group consisting of amine groups having the formula —NR
8
R
9
and sulfur moieties having the formula —SR
10
wherein R
8
and R
9
are individually an aliphatic moiety of from about 1 to about 22 carbon atoms, —(C
a
H
2a
O)
n
H wherein a is 2, 3, or 4 and n is from about 1 to about 20 or 2-hydroxyl-2-phenylethyl, R
8
and R
9
with N optionally forming a heterocyclic moiety having from about 2 to about 8 carbon atoms and R
10
is selected from the group consisting of straight or branched chain aliphatic moieties having from 1 to about 22 carbon atoms, phenyl and a heterocyclic moieties containing N, S or O and having from about 2 to about 8 carbon atoms in the ring. Compositions containing compounds of the general formula (II) can also contain copper ions to enhance performance.
In yet another embodiment the preservative composition comprises a compound having the formula:
wherein X
−
is an anion; R
11
, R
12
, R
13
can be the same or different and are selected from the group consisting of R
14
, straight or branched chain aliphatic moieties of from 1 to about 22 carbon atoms, and benzyl moieties optionally having one or more ring substituent selected from the group consisting of chloro, methyl, ethyl, propyl, bromo, iodo, fluoro, trifluoromethyl, hydroxy, methoxy and phenyl; R
14
is —(CH
2
—CHR
15
—O)
x
R
16
wherein x is 1 to 20, R
15
is hydrogen, methyl, ethyl or phenyl, and R
16
selected from the group consisting of benzyl, napthobenzyl and picoyl moieties optionally having one or more ring substituent selected from the group consisting of chloro, methyl, ethyl, propyl, bromo, iodo, fluoro, trifluoromethyl, hydroxy, methoxy and phenyl, or R
16
is —(CH
2
)
y
R
17
wherein y is from 1 to about 5 and R
17
is a moiety selected from the group consisting of nitrogen-containing heterocyclic groups having 5 to 8 members in the ring, such as, for example morpholin-4-yl, piperidin-1-yl and pyrrolidin-1-yl groups.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENT(S)
The preservatives described herein are compositions having a biocidal effect on microorganisms such as bacteria, algae, mold and fungus, thereby preventing rotting and deterioration. While these compositions are particularly adapted for use as preservatives for wood, they are also generally useful in applications where biocides are needed such as preservatives for cotton, and for metalworking fluids, recirculating water systems, cooling water systems, and swimming pools, for example.
In one embodiment the biocidal preservative composition includes a compound of formula (II):
wherein X
−
is an anion such as, but not limited to, chloride, fluoride, bromide, iodide, acetate, methylsulfate, formate, carbonate, methylcarbonate, nitrate, nitrite, hydroxide, borate, tetraborate, perchlorate, periodate, and phosphate. Preferably, X
−
is a halide, most preferably chloride.
The value of y in the general formula I can vary from 1 to about 12. Preferably, y is from 1 to about 3. Most preferably, y=1.
R
1
, R
2
, and R
3
can be the same or different and are independently selected from a straight or branched chain aliphatic moiety of from about 1 to about 22 carbon atoms, a benzyl moiety with or without substituents, —(C
a
H
2a
O)
n
H wherein a is 2, 3, or 4 and n is from about 1 to about 20, 2-hydroxyl-2-phenylethyl. Optionally, R
1
and R
2
with N
+
can form a heterocyclic moiety having from about 4 to about 10 carbon atoms, such as a pyrrole, piperidine or morpholine ring.
Preferably, at least one of R
1
, R
2
and R
3
should be a saturated or unsaturated, straight or branched chain aliphatic moiety of from about 1 to about 22 carbon atoms, more preferably from about 6 to about 22 carbon atoms, most preferably 10 to 18 carbon atoms. The aliphatic moiety may have a fixed chain length or may be of mixed chain length such as those groups derived from natural fats or oils or petroleum stocks. Preferably, the aliphatic moiety is a fatty aliphatic such as tallow alkyl, rapeseed alkyl, oleyl, cocoalkyl, soya alkyl and the like. Most preferred is cocoalkyl. In particularly useful embodiment, R
1
is a C
10
to C
18
aliphatic moiety and R
2
and R
3
are independently selected from C
1
to C
3
alkyl moieties, most preferably —CH
3
. Thus, preferred compounds of formula (I) include dimethylcocoalkyl(thiocyanatomethyl) ammonium chlorides and dimethyldodecyl(thiocyanatomethyl)ammonium chloride.
Compounds of formula (I) can be made in accordance with the following procedure:
A haloalkyl thiocyanate is reacted with an amine compound having the formula
wherein R
1
, R
2
and R
3
are as specified above, to produce a compound of formula (I).
In a preferred embodiment, the haloalkyl thiocyanate is prepared by reacting a compound of the formula X(CH
2
)
y
Br wherein y is from 1 to about 12, X is a halogen with a
Bell John P.
Doyle Andress K.
Farmer Robert F.
Gadberyy James F.
Lucas Douglas
Akzo Nobel N.V.
Dilworth & Barrese
Qazi Sabiha N.
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