Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2000-06-12
2002-06-04
Vollano, Jean F. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C562S008000
Reexamination Certificate
active
06399827
ABSTRACT:
BACKGROUND OF THE INVENTION
(a) Field of the Invention
The present invention relates to a novel quaternary ammonium phosphate compound and, more particularly, to a quaternary ammonium phosphate compound having the following formula 1 and which has an anticorrosive and a biocidal effect and an efficient method of preparing the same.
In the above formula 1, R
1
is a straight or a branched alkyl or aryl radical with 1 to 27 of carbon atom(s) free of —OH group and may contain hetero-atoms, and both of R
2
and R
3
are methyl groups or R
2
and R
3
are combined to form a heterocyclic compound with 4 to 6 of carbon atoms containing oxygen and nitrogen.
(b) Description of the Related Arts
A quaternary ammonium halide containing a quaternary ammonium salt as a parental core, particularly, a quaternary ammonium chloride has the advantages of having, a high biocidal effect and a low degree of surface tension and toxicity and hence, it is often used for the purpose of cleaning and sterilizing various household and industrial goods. And it is also widely used as an additive in wood preservatives, paints, industrial water-treating agents, cleansers and biocides because it is highly stable.
A quaternary ammonium halide is typically prepared by using the following reaction formula.
R
1
R
2
R
3
N+R
4
X→R
1
R
2
R
3
R
4
NX Reaction formula 1
In the above reaction formula 1, R
1
, R
2
, R
3
and R
4
are independently alkyl or aryl radicals and X is a halogen compound.
Recently, quaternary ammonium chlorides, particularly, N-alkyl-N-benzyl-N-dimethyl ammonium chloride and N-dialkyl-N-dimethyl ammonium chloride have been the subject of many studies. They are disclosed in U.S. Pat. Nos. 3,919,143 and 3,910,866 as polymer hardening promoters, disclosed in U.S. Pat. No. 5,300,635 as surfactants for separation of RNA and disclosed in U.S. Pat. Nos. 5,290,805, 5,399,762, 5,561,187 and 5,567,372 as common biocides. U.S. Pat. No. 4,929,454 and Journal of American Wood Preservativer's Association(1987) pages 331~348 by A. F. Preston disclose a technique for preserving wood by impregnating the quaternary ammonium chloride in the wood.
U.S. Pat. No. 4,521,412 discloses iodopropargylammonium salts having a pesticidal effect and a method of preparing the same, and U.S. Pat. No. 5,266,567 discloses halopropargylated cyclic quaternary ammonium compounds and a method of preparing the same.
But all the above-described compounds have a high biocidal effect in a water system, but as they release halogen compounds such as fluorine, chlorine, bromine and iodine, they are difficult to apply to corrosive metal substances such as carbon steels, cast irons, stain steels or coppers. Accordingly, U.S. Pat. No. 5,438,034 (1995) discloses a quaternary ammonium carbonate and a method of preparing the same, the quaternary ammonium carbonate having the following formula 5 and which has no metal coupler and which can be obtained easily to be used as a wood preservative. The method adopts directly a gaseous or solid carbon dioxide as a carbonic acid of a reactant.
In the above formula 5, both R
1
and R
2
are alkyl groups with 8 to 12 of carbon atoms.
U.S. Pat. No. 5,399,762 (1995) discloses a quaternary ammonium hydroxide and a method of preparing the same, the quaternary ammonium hydroxide being used as a wood preservative. An aqueous solution containing 80% quaternary ammonium chloride is used as a starting material and the equilibrium of a reaction is shifted by raising a temperature to 40~90° C. so that the quaternary ammonium hydroxide can be prepared. However, if the temperature is raised as in the above, a parental core of the quaternary ammonium salt undergoes a Hofmann elimination and rearrangement reaction when the parental core is exposed under a high-temperature alkaline condition so that a yellowish-brown oily olefin and amine compounds emitting an amine ordor are formed. The compounds are highly hygroscopic and difficult to separate. In addition, in drying the ammonium hydroxide, a considerable quantity of the compound is decomposed.
Moreover, all the above-described compounds have been developed and designed only as common biocides and except for the quaternary ammonium hydroxide, they are limited to a structure that a leaving group of a reactant are ion-bonded with the quaternary ammonium salt as an anionic conjugate of the compound
In another aspect, United Kingdom Patent No. 1,199, 015 (1968) and U.S. Pat. No. 4,252,662 (1981) disclose a method of introducing a phosphoric ester as an anionic conjugate. However, this method adopts the phosphoric ester as a reactant and is applied in the field of a base material of a high-pressure fluid. And U.S. Pat. No. 4,716,037 discloses a quaternary ammonium compound having an alkyl group with a terminal alcoholic group and which is used in hair conditioners for the purpose of lessening corrosion of stain steels.
SUMMARY OF THE INVENTION
It is an object of the present invention to provide a quaternary ammonium phosphate compound having the following formula 1 and which has both a strong anticorrosive effect on a wide range of metals and biocidal effect to be used in corrosive metal substances such as carbon steels, iron casts, stain steels, coppers, tinning steel plates and alumina by substituting a dihydrogen phosphate ion(H
2
PO
4
,) for a Cl ion from a quaternary ammonium chloride, and a method of preparing the same.
Particularly, a novel quaternary ammonium phosphate compound having the following formula 1 is characterized in that it has an ether group including an unshared electron pair to improve an anticorrosive characteristic greatly and to be able to form a nonoxidative anticorrosive membrane.
A first aspect of the present invention provides a quaternary ammonium phosphate compound having the following formula 1.
In the above formula, R
1
is a straight or a branched alkyl radical with 1 to 27 carbon atoms or aryl radical with 6 to 27 carbon atoms which does not contain —OH groups as substitutents on the carbon atoms, and may contain heteroatoms in the alkyl or aryl chain; and both of R
2
and R
3
are methyl groups or R
2
and R
3
are combined to form a heterocyclic compound with 4 to 6 carbon atoms containing oxygen and nitrogen.
R
1
is preferably p-(&agr;,&agr;,&ggr;,&ggr;)-tetramethyl butyl phenoxy ethoxy ethyl group, and R
2
and R
3
are preferably methyl groups.
And R
1
is preferably a tetradecyl group, and R
2
and R
3
are preferably morpholinium groups having the following formula 2.
The second aspect of the present invention provides a method of preparing a quaternary ammonium phosphate compound having the above formula 1 having the step of reacting a quaternary ammonium hydroxide having the following formula 3 with a phosphoric acid.
In the above formula 3, R
1
, R
2
and R
3
are the same as defined above.
The quaternary ammonium hydroxide is preferably prepared by reacting a solid quaternary ammonium chloride having the following formula 4 with a metal hydroxide of 1.05~2.0 equivalents to the quaternary ammonium chloride in a solvent containing an alcohol with 1 to 4 of carbon atom(s) at 0~35° C.
In the above formula 4, R
1
, R
2
and R
3
are the same as defined above.
The third aspect of the present invention provides a composition having an anticorrosive and a biocidal effect, containing a quaternary ammonium phosphate compound having the above formula 1.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
A quaternary ammonium phosphate compound having the above formula 1 is prepared as follows.
Reaction formula 2
A quaternary ammonium chloride contains a N-benzyl group in a parental core of a quaternary ammonium salt and is preferably selected from the group consisting of N-dimethyl-N-[p-((&agr;,&agr;,&ggr;,&ggr;)-tetramethyl butyl phenoxy]ethoxy ethyl-N-benzyl ammonium chloride, a mixture of N-dimethyl-N-dodecyl-N-benzyl ammonium chloride, N-dimethyl-N-tetradecyl-N-benzyl ammonium chloride, N-dimethyl-N-hexadecyl-N-benzyl ammonium chloride and N-dimethyl-N-octadecyl-N-benzyl ammonium chloride, and 4-
Cho Chang-Mook
Choi Dong-Jin
Ha Jae-Min
Hahn Soon-Jong
Park Jun-Weon
Baker & Botts L.L.P.
SK Chemicals
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