U.S. patent application number 10/515708 was filed with the patent office on 2006-06-22 for novel imidazole alcohol compound, process for producing the same, and surface-treating agent comprising the same.
Invention is credited to Toru Imori, Junnosuke Sekiguchi, Atsushi Yabe.
Application Number | 20060135584 10/515708 |
Document ID | / |
Family ID | 31184740 |
Filed Date | 2006-06-22 |
United States Patent
Application |
20060135584 |
Kind Code |
A1 |
Imori; Toru ; et
al. |
June 22, 2006 |
Novel imidazole alcohol compound, process for producing the same,
and surface-treating agent comprising the same
Abstract
It is an object of the present invention to provide a novel
imidazole alcohol compound that adheres strongly to metal surfaces
in metal products, especially copper, aluminum and steel products,
and that has a superior rust-preventive effect even in a thin film,
and a surface-treating agent using the same. The novel imidazole
alcohol compound is expressed by the following general formula (1)
show a rust-preventive effect. ##STR1## (In general formula (1),
R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, a vinyl group or an
alkyl group with 1 to 20 carbon atoms, an aromatic ring may be
formed by R.sup.2 and R.sup.3, X indicates hydrogen, an alkyl group
with 1 to 6 carbon atoms, or a substituent group which may contain
N or O, m indicates an integer from 0 to 20, and n and 1 indicate
integers from 1 to 3.) The above-mentioned imidazole alcohol
compound can be produced by reacting an imidazole compound and an
epoxy alcohol compound.
Inventors: |
Imori; Toru;
(Kitaibaraki-shi, JP) ; Yabe; Atsushi;
(Kitaibaraki-shi, JP) ; Sekiguchi; Junnosuke;
(Kitaibaraki-shi, JP) |
Correspondence
Address: |
FLYNN THIEL BOUTELL & TANIS, P.C.
2026 RAMBLING ROAD
KALAMAZOO
MI
49008-1631
US
|
Family ID: |
31184740 |
Appl. No.: |
10/515708 |
Filed: |
July 16, 2003 |
PCT Filed: |
July 16, 2003 |
PCT NO: |
PCT/JP03/09072 |
371 Date: |
November 23, 2004 |
Current U.S.
Class: |
514/396 ;
548/341.1 |
Current CPC
Class: |
C07D 249/08 20130101;
C07D 233/56 20130101; C07D 231/12 20130101; C07D 233/54 20130101;
Y10T 428/31678 20150401; C23F 11/149 20130101 |
Class at
Publication: |
514/396 ;
548/341.1 |
International
Class: |
C07D 233/54 20060101
C07D233/54; A61K 31/4164 20060101 A61K031/4164 |
Foreign Application Data
Date |
Code |
Application Number |
Jul 29, 2002 |
JP |
202-219716 |
Claims
1. A Novel imidazole alcohol compound expressed by the following
general formula (1). ##STR6## (In general formula (1), R.sup.1,
R.sup.2 and R.sup.3 are each hydrogen, a vinyl group or an alkyl
group with 1 to 20 carbon atoms, an aromatic ring may be formed by
R.sup.2 and R.sup.3, X indicates hydrogen, an alkyl group with 1 to
6 carbon atoms, or a substituent group which may contain N or O, m
indicates an integer from 0 to 20, and n and l indicate integers
from 1 to 3.)
2. A process for producing the imidazole alcohol compound according
to claim 1, characterized by reacting an imidazole compound
expressed by the following general formula (2) and an epoxy alcohol
compound expressed by the following general formula (3). ##STR7##
(In general formula (2), R.sup.1, R.sup.2 and R.sup.3 are each
hydrogen, a vinyl group or an alkyl group with 1 to 20 carbon
atoms, and an aromatic ring may be formed by R.sup.2 and R.sup.3,
and in general formula (3), X indicates hydrogen, an alkyl group
with 1 to 6 carbon atoms, or a substituent group which may contain
N or O, m indicates an integer from 0 to 20, and n and l indicate
an integer from 1 to 3.)
3. A surface-treating agent comprising the imidazole alcohol
compound according to claim 1 as an active ingredient.
Description
TECHNICAL FIELD
[0001] The present invention relates to novel imidazole alcohol
compounds, a method for producing the same, and a surface-treating
agent comprising the same as an active ingredient.
BACKGROUND ART
[0002] There are various requirements for the surfaces of various
metal materials; rust-preventive properties may be cited as one
important characteristic. Iron and steel products are used in
various applications such as structures, automobiles, ships, cans
and the like; in such applications, there are strong requirements
for rust-preventive properties. Conventionally, various types of
rust-preventive agents such as water-soluble rust-preventive
agents, vaporizable rust-preventive agents, oil-based
rust-preventive agents and the like have been used to obtain
rust-preventive properties in iron and steel products. Generally,
water-soluble rust-preventive agents are used for the purpose of
temporary short-term rust prevention, and are not used for
long-term rust prevention. Furthermore, vaporizable rust-preventive
agents show an inherent rust-preventive power in a sealed state.
Oil-based rust-preventive agents have a relatively strong
rust-preventive power, and are able to provide long-term rust
prevention; such agents include liquid-form rust-preventive oils,
viscous rust-preventive greases, and agents in which
rust-preventive additives, film forming additives or the like are
dissolved in volatile organic solvents. However, rust-preventive
oils and rust-preventive greases show stickiness following a
surface treatment, and cannot be used as undercoating materials
such as coating films or the like. Furthermore, agents formed by
dissolving rust-preventive additives, film forming additives or the
like in volatile organic solvents do no manifest a sufficient
rust-preventive effect unless a thick film thickness is formed.
[0003] Moreover, zinc-plated steel plates are commercially marketed
for the purpose of suppressing rust on iron. However, such plates
prevent the rust of iron by means of a sacrificial anti-corrosion
effect of zinc, which has a greater tendency toward ionization than
iron. In this case, white rust of the zinc layer is prevented by
further subjecting the surface of the zinc plating layer to a
chemical conversion treatment such as a chromate treatment or the
like, so that the rust-preventive properties are greatly
reinforced. However, although such a chromate treatment produces a
high rust-preventive effect even in a thin coating film, there is a
demand for a rust-preventive coating film to replace this chromate
treatment because of environmental problems. Currently, tannic acid
has been proposed as a rust-preventive agent for zinc-plated steel
plates; at present, however, it cannot be said that this has a
sufficient effect compared to a chromate treatment.
[0004] Aluminum or aluminum alloys are light in weight, and have
therefore attracted attention in various fields. However, since an
aluminum oxide coating film is formed on the surface, the adhesion
is not sufficient even in cases where the aluminum is directly
coated with a paint. Numerous methods have been proposed as
chemical conversion treatment methods for paint primary coating or
undercoating, and numerous patent applications have currently been
filed. At the present time, however, chromate treatment methods
constitute the mainstream in the United States and Japan. However,
as in the case of the above-mentioned-zinc-plated steel plates,
chromate treatments are undesirable from the standpoint of the
environment, and there is a demand for a non-chromate treatment.
Moreover, methods in which a treatment is performed with an alkali
metal salt aqueous solution of silicic acid for the purpose of
endowing the metal surface with characteristics such as corrosion
resistance, static resistance and the like have also been proposed.
In such methods, however, the treatment temperature is high, an
immersion in boiling water or an immersion in an acid is performed
as an after-treatment, and the desired characteristics cannot be
obtained unless the alkali metal is removed.
DISCLOSURE OF THE INVENTION
[0005] It is an object of the present invention to provide novel
imidazole alcohol compounds that can meet such requirements, i. e.,
that adhere strongly to metal surfaces in metal products,
especially copper, aluminum and iron and steel products, and that
have a superior rust-preventive effect even in a thin film, and a
surface-treating agent using the same.
[0006] As a result of diligent research, the present inventors
discovered that novel imidazole alcohol compounds expressed by the
following general formula (1) have a superior rust-preventive
effect on metal surfaces.
[0007] The present invention was devised on the basis of such a
finding; the gist of this invention is as shown in (1) through (3)
below.
[0008] (1) A novel imidazole alcohol compound expressed by the
following general formula (1). ##STR2## (In general formula (1),
R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, a vinyl group or an
alkyl group with 1 to 20 carbon atoms, an aromatic ring may be
formed by R.sup.2 and R.sup.3, X indicates hydrogen, an alkyl group
with 1 to 6 carbon atoms, or a substituent group which may contain
N or O, m indicates an integer from 0 to 20, and n and l indicate
integers from 1 to 3.)
[0009] (2) A process for producing the imidazole alcohol compound
according to the above-mentioned (1), characterized by reacting an
imidazole compound expressed by the following general formula (2)
and an epoxy alcohol compound expressed by the following general
formula (3). ##STR3##
[0010] (In general formula (2), R.sup.1, R.sup.2 and R.sup.3 are
each hydrogen, a vinyl group or an alkyl group with 1 to 20 carbon
atoms, and an aromatic ring may be formed by R.sup.2 and R.sup.3,
and in general formula (3), X indicates hydrogen, an alkyl group
with 1 to 6 carbon atoms, or a substituent group which may contain
N or O, m indicates an integer from 0 to 20, and n and l indicate
an integer from 1 to 3.)
[0011] (3) A surface-treating agent comprising the imidazole
alcohol compound according to the above-mentioned (1) as an active
ingredient.
[0012] The present invention will be described in greater detail
below.
[0013] The effect of the present invention is sufficiently
manifested if R.sup.1, R.sup.2 and R.sup.3 in the above-mentioned
general formulae (1) through (3) indicate hydrogen, vinyl groups or
alkyl groups with 1 to 20 carbon atoms. Alkyl groups with 1 to 20
carbon atoms are desirable as alkyl groups. Furthermore, in cases
where an aromatic ring is formed by R.sup.2 and R.sup.3, it is
desirable that the aromatic ring that is formed be a benzene ring.
X indicates hydrogen, an alkyl group with 1 to 6 carbon atoms, or a
substituent group that may contain N or O. An alkyl group with 1 to
4 carbon atoms is desirable as the alkyl group with 1 to 6 carbon
atoms, and hydroxy groups, carboxyl groups, amino groups and the
like may be cited as examples of substituent groups that contain N
or O.
[0014] The above-mentioned imidazole alcohol compounds (1) of the
present invention are synthesized by the reaction expressed by the
following reaction formula (4). Specifically, these compounds can
be produced by mixing an imidazole compound and an epoxy alcohol
compound, and heating this mixture to a temperature of 80 to
200.degree. C. ##STR4## (In the above formula, R.sup.1, R.sup.2,
R.sup.3, X, l, m and n have the same definitions as described
above.
[0015] Examples of desirable imidazole compounds expressed by the
above-mentioned general formula (2) include imidazole,
2-alkylimidazoles, 2,4-dialkylimidazoles, 4-vinylimidazoles and the
like. Especially desirable among these are imidazole;
2-methylimidazole, 2-ethylimidazole and 2-undecylimidazole as
2-alkylimidizoles; and 2-ethyl-4-methylimidazole and the like as
2,4-dialkylimidazoles.
[0016] Desirable examples of epoxy alcohol compounds expressed by
the above-mentioned general formula (3) include epoxypropanol,
epoxybutanol, epoxypentanol, epoxyhexanol and the like, and
epoxypropanol is especially desirable.
[0017] It is advisable that the reaction of the above-mentioned
imidazole compound and epoxy alcohol compound be performed by
adding the epoxy alcohol compound dropwise to the imidazole
compound heated to a temperature of 80 to 200.degree. C wherein the
amount of the epoxy alcohol compound added is 0.1 to 10 times by
mole as much as that of the imidazole compound. A reaction time of
approximately 5 minutes to 2 hours is sufficient. This reaction
does not always need a solvent; however, an organic solvent such as
chloroform, dioxane, methanol, ethanol or the like may be used as a
reaction solvent. Furthermore, since this reaction is averse to
moisture, it is desirable to perform the reaction in a gas
atmosphere that contains no moisture such as dried nitrogen, argon
or the like, in order to prevent the inclusion of moisture.
[0018] The compounds of the present invention expressed by the
above-mentioned general formula (1) can also be used as chemical
mechanical polishing additives or wetting working agents; however,
these compounds are especially useful as rust-preventive agents.
When the imidazole alcohol compounds of the present invention are
used on metals as surface-treating agents, it is generally
desirable that these compounds be used in a form in which the
compounds are diluted in a solvent. In this case, solvent-soluble
resins (epoxy resins, acrylic resins or the like), silane coupling
agents, viscosity adjusting agents, defoaming agents, ultraviolet
absorbing agents, preservatives, surfactants and the like may also
be added.
[0019] Solvents used in cases where the imidazole alcohol compounds
of the present invention are used as surface-treating agents may be
either aqueous type solvents or solvent type solvents. Examples of
solvent type solvents include methanol, ethanol, isopropanol,
toluene, ethyl acetate and the like.
[0020] The surface-treating agent of the present invention is used
on metals; this agent has an especially superior rust-preventive
effect on copper and copper alloys. Universally known coating
methods such as spray coating, dip coating, brush coating and the
like can be employed as the coating method used to apply the
surface-treating agent of the present invention to a metal
surface.
[0021] In order to obtain the effect of the surface-treating agent
of the present invention to a sufficient extent, it is desirable
that the agent be dried by heating following application as a
coating. In this drying by heating, it is desirable that the
coating be dried for 30 seconds to 60 minutes at 100 to 230.degree.
C. Under heating conditions following coating, the adsorption to
the metal is heightened by the removal of moisture, so that the
rust-preventive effect is enhanced. It is desirable that the
thickness of the coating film following drying be 0.01 to 100
.mu.m. A thickness of 0.05 to 10 .mu.m is even more desirable. If
the thickness is less than 0.01 .mu.m, sufficient rust-preventive
properties cannot be imparted, and if the thickness exceeds 100
.mu.m, a uniform coating film cannot be obtained.
BRIEF DESCRIPTION OF THE DRAWINGS
[0022] FIG. 1 shows the .sup.1H-NMR spectrum of the novel imidazole
alcohol compound of the present invention obtained in Example
1.
[0023] FIG. 2 shows the results of Auger analysis for Example
2.
[0024] FIG. 3 shows the results of Auger analysis for Example
1.
BEST MODE FOR CARRYING OUT THE INVENTION
[0025] The present invention will be concretely described below in
terms of examples.
Example 1
Synthesis of Imidazole Alcohol Compound
[0026] 9.2 g of imidazole was heated to 120.degree. C, and 10 g of
2,3-epoxypropanol was added to this dropwise. Afterward, a reaction
was performed for 3 hours at 150.degree. C., thus producing 19 g of
the target product indicated by the following formula (5). The
compound thus obtained was identified by NMR measurement. The
.sup.1H-NMR spectrum of this compound is shown in FIG. 1.
##STR5##
Example 2
Use as Surface-treating Agent
[0027] A 10% aqueous solution (pH 11.6) of the imidazole alcohol
compound (5) obtained in Example 1 was applied as a coating to the
surface of a copper foil, and was heat-treated for 30 minutes at
150.degree. C. Subsequently, Auger analysis was performed at an
etching rate of 100 angstroms/min (calculated as SiO.sub.2). The
results are shown in FIG. 2. It is seen from FIG. 2 that a high
rust-preventive effect was manifested at a high pH with little
oxygen detected.
Comparative Example 1
[0028] An experiment similar to the examples was performed, except
that the copper foil was not coated with the compound of the
present invention. Auger analysis was performed in the same manner.
The results are shown in FIG. 3.
INDUSTRIAL APPLICABILITY
[0029] Compositions containing the imidazole alcohol compounds of
the invention show superior rust-preventive properties.
* * * * *