CN102144046B - 2-benzyl-4-(3,4-dichlorophenyl)-5-methylimidazole compound - Google Patents

2-benzyl-4-(3,4-dichlorophenyl)-5-methylimidazole compound Download PDF

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CN102144046B
CN102144046B CN200980134515.8A CN200980134515A CN102144046B CN 102144046 B CN102144046 B CN 102144046B CN 200980134515 A CN200980134515 A CN 200980134515A CN 102144046 B CN102144046 B CN 102144046B
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dichlorophenyl
methylimidazole
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hydrochloric acid
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村井孝行
平尾浩彦
高作康司
宫崎真幸
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Shikoku Chemicals Corp
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Abstract

An object is to provide a 2-benzyl-4-(3,4-dichlorophenyl)-5-methylimidazole compound useful as an antioxidant for copper surface, a curing agent for epoxy resins, or an intermediate for medicaments and agricultural chemicals. A 2-benzyl-4-(3,4-dichlorophenyl)-5-methylimidazole compound represented by the formula (I). The compound can be synthesized by reacting a 2-halogenated 3',4'-dichloropropiophenone compound with an arylacetamidine compound under heating in the presence of a dehydrohalogenating agent in an organic solvent. wherein X1 and X2 are the same or different and represent a hydrogen atom, a chlorine atom, or a bromine atom.

Description

2-phenmethyl-4-(3,4-dichlorophenyl)-5-methylimidazole compound
Technical field
The present invention relates to a kind of novel 2-phenmethyl-4-(3,4-dichlorophenyl)-5-methylimidazole compound.
Background technology
As with the similar imidazolium compounds of the compounds of this invention, 2-(2,4 dichloro benzene methyl)-5-(3,4-dichlorophenyl)-1H-imidazoles is for example disclosed in patent documentation 1.Yet, in described document, the imidazolium compounds on unexposed 4 (5) positions that methyl are bonded to imidazole ring.
Reference listing
Patent documentation
Patent documentation 1: Japanese Unexamined Patent Application Publication 2003-500357 communique (the 7th page, the 51st page)
Summary of the invention
The object of this invention is to provide a kind of novel 2-phenmethyl-4-(3,4-dichlorophenyl)-5-methylimidazole compound.
In order to address the above problem, the inventor has carried out extensive and deep research.As a result, the inventor finds, can synthesize novel 2-phenmethyl-4-(3,4-the dichlorophenyl)-5-methylimidazole compound being represented by formula (I), and thus, they have completed the present invention.
That is, the present invention its most widely configuration comprise following aspect:
(1) a kind of 2-phenmethyl-4-(3,4-dichlorophenyl)-5-methylimidazole compound being represented by formula (I):
Figure BPA00001328169100021
X wherein 1and X 2identical or different and represent hydrogen atom, chlorine atom or bromine atoms.
2-phenmethyl-4-(3 of the present invention, 4-dichlorophenyl)-5-methylimidazole compound can be used as the surperficial antioxidant of metal, particularly copper (comprising copper alloy), with solidifying agent or the curing catalyst of epoxy resin, also can be used as the intermediate raw material in medicine and pesticide field.
Embodiment
Below the present invention is described in detail.
2-phenmethyl-4-of the present invention (3,4-dichlorophenyl)-5-methylimidazole compound is that the compound and the example that by following formula (I), are represented comprise:
2-phenmethyl-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(2-chlorophenylmethyl)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(3-chlorophenylmethyl)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(4-chlorophenylmethyl)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(2,3-dichlorobenzene methyl)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(2,4 dichloro benzene methyl)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(2,5-dichlorobenzene methyl)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(2,6-dichlorobenzene methyl)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(3,4-dichlorobenzene methyl)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(3,5-dichlorobenzene methyl)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(2-Brombenzyl)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(3-Brombenzyl)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(4-Brombenzyl)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(2,3-dibromobenzene methyl)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(2,4-dibromobenzene methyl)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(2,5-dibromobenzene methyl)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(2,6-dibromobenzene methyl)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(3,4-dibromobenzene methyl)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(3,5-dibromobenzene methyl)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(the bromo-2-chlorophenylmethyl of 3-)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(the bromo-2-chlorophenylmethyl of 4-)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(the bromo-2-chlorophenylmethyl of 5-)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(the bromo-6-chlorophenylmethyl of 2-)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(the bromo-3-chlorophenylmethyl of 2-)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(the bromo-3-chlorophenylmethyl of 4-)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(the bromo-3-chlorophenylmethyl of 5-)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(the bromo-5-chlorophenylmethyl of 2-)-4-(3,4-dichlorophenyl)-5-Methylimidazole, 2-(the bromo-4-chlorophenylmethyl of 2-)-4-(3,4-dichlorophenyl)-5-Methylimidazole and 2-(the bromo-4-chlorophenylmethyl of 3-)-4-(3,4-dichlorophenyl)-5-Methylimidazole.
Figure BPA00001328169100031
X wherein 1and X 2identical or different and represent hydrogen atom, chlorine atom or bromine atoms.
Can be according to synthetic 2-phenmethyl-4-of the present invention (3,4-the dichlorophenyl)-5-methylimidazole compound of known method.For example, as shown in following reaction scheme, by organic solvent, under the existence of dehydrohalogenation reagent heating under make 3 of 2-halogenation ', 4 '-dichloropropiophenone compound reacts with aryl ethanamidine compound, can synthesize described compound.
Figure BPA00001328169100041
X wherein 1and X 2same as described above and X 3represent chlorine atom, bromine atoms or iodine atom.
In above-mentioned reaction, the consumption of aryl ethanamidine compound with respect to 3 of 2-halogenation ', the ratio of 4 '-dichloropropiophenone compound is preferably 0.8～1.5 times mole, more preferably 0.9～1.1 times mole.The consumption of dehydrohalogenation reagent with respect to 3 of 2-halogenation ', the ratio of 4 '-dichloropropiophenone compound is preferably 1～10 times of equivalent.
As 3 of above-mentioned 2-halogenation ', 4 '-dichloropropiophenone compound, can mention have 2-chloro-3 ', 4 '-dichloropropiophenone, 2-be bromo-3 ', 4 '-dichloropropiophenone and 2-be iodo-3 ', 4 '-dichloropropiophenone.
By to 3 ', 2 of 4 '-dichloropropiophenone carry out halogenation obtain 3 of 2-halogenation ', 4 '-dichloropropiophenone compound.As halogenation, chlorination or iodate are also feasible, but make the bromine and 3 of equimolar amount ', 4 ' bromination reaction that-dichloropropiophenone reacts is the most simply and most convenient.
As 3 ', 4 '-dichloropropiophenone, can be used commercially available material as reagent.
By aryl B amidine hydrochloric acid salt being reacted with alkaline agent and removing de-chlorine hydride, can obtain above-mentioned aryl ethanamidine compound.In the above-mentioned building-up reactions of imidazolium compounds, also can replace aryl ether compound with conventional known mineral acid or organic acid salt with aryl B amidine hydrochloric acid salt or aryl ethanamidine compound.
Can be according to the synthetic described aryl B amidine hydrochloric acid salt of known method.For example, as shown in following reaction scheme, by making benzyl cyanide compound and hydrogen chloride gas and lower alcohol react to change into aryl B amidine hydrochloric acid salt as ethanol, and further make itself and ammonia react, can synthesizing aryl B amidine hydrochloric acid salt.
Figure BPA00001328169100051
X wherein 1and X 2same as described above.
The example of the hydrochloride of the aryl ethanamidine compound obtaining by this reaction comprises:
Phenylacetamidino hydrochloride, (2-chloro-phenyl-) B amidine hydrochloric acid salt, (3-chloro-phenyl-) B amidine hydrochloric acid salt, (4-chloro-phenyl-) B amidine hydrochloric acid salt, (2,3-dichlorophenyl) B amidine hydrochloric acid salt, (2,4 dichloro benzene base) B amidine hydrochloric acid salt, (2,5-dichlorophenyl) B amidine hydrochloric acid salt, (2,6-dichlorophenyl) B amidine hydrochloric acid salt, (3,4-dichlorophenyl) B amidine hydrochloric acid salt, (3,5-dichlorophenyl) B amidine hydrochloric acid salt, (2-bromophenyl) B amidine hydrochloric acid salt, (3-bromophenyl) B amidine hydrochloric acid salt, (4-bromophenyl) B amidine hydrochloric acid salt, (2,3-dibromo phenyl) B amidine hydrochloric acid salt, (2,4-dibromo phenyl) B amidine hydrochloric acid salt, (2,5-dibromo phenyl) B amidine hydrochloric acid salt, (2,6-dibromo phenyl) B amidine hydrochloric acid salt, (3,4-dibromo phenyl) B amidine hydrochloric acid salt, (3,5-dibromo phenyl) B amidine hydrochloric acid salt, (the bromo-2-chloro-phenyl-of 3-) B amidine hydrochloric acid salt, (the bromo-2-chloro-phenyl-of 4-) B amidine hydrochloric acid salt, (the bromo-2-chloro-phenyl-of 5-) B amidine hydrochloric acid salt, (the bromo-6-chloro-phenyl-of 2-) B amidine hydrochloric acid salt, (the bromo-3-chloro-phenyl-of 2-) B amidine hydrochloric acid salt, (the bromo-3-chloro-phenyl-of 4-) B amidine hydrochloric acid salt, (the bromo-3-chloro-phenyl-of 5-) B amidine hydrochloric acid salt, (the bromo-5-chloro-phenyl-of 2-) B amidine hydrochloric acid salt, (the bromo-4-chloro-phenyl-of 2-) B amidine hydrochloric acid salt and (the bromo-4-chloro-phenyl-of 3-) B amidine hydrochloric acid salt.
As above-mentioned dehydrohalogenation reagent, can use any one known reagent and unrestricted.The example of this dehydrohalogenation reagent comprises that inorganic alkaline compound is as sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, salt of wormwood, sodium bicarbonate and saleratus; Organo-alkali compound is as triethylamine and 1,8-diazabicyclo [5.4.0]-7-undecylene (DBU); Metallic alkoxide compound is as sodium methylate and potassium tert.-butoxide; Etc..
As above-mentioned reaction solvent, can use any one known solvent and unrestricted, as long as its can dissolve 3 of 2-halogenation ', 4 '-dichloropropiophenone compound and aryl ethanamidine compound and do not participate in described reaction.The example of this solvent comprises that alcohols is as Virahol and the trimethyl carbinol; Hydro carbons is as hexane and toluene; Halogenated hydrocarbons is as chloroform and chlorobenzene; Ester class is as ethyl acetate; Nitrile is as acetonitrile; Ethers is as tetrahydrofuran (THF), two
Figure BPA00001328169100061
alkane and glycol dimethyl ether; Amides is as DMF (DMF) and N,N-dimethylacetamide (DMAC); Methyl-sulphoxide (DMSO); Etc..Can use these solvents in the mode of combination.
Temperature of reaction is preferably from room temperature to reflux temperature and the reaction times is preferably 1～10 hour.Conventionally can under barometric point, implement described reaction.
By common aftertreatment, can carry out separation to the 2-phenmethyl-4-forming (3,4-dichlorophenyl)-5-methylimidazole compound under above-mentioned reaction conditions.For example, by the reaction mixture after having reacted being distributed between water layer and organic solvent layer, and utilizing water organic solvent to be evaporated after organic solvent layer is washed, can access the crude product of described compound, and can further purify to described crude product by recrystallization operation etc.
Embodiment
Below with reference to embodiment, the present invention is specifically described, but should not be construed, the present invention is limited to this.Incidentally, reference example 1 and 2 shown respectively phenylacetamidino hydrochloride and 2-bromo-3 ', the synthesis example of 4 '-dichloropropiophenone.
Reference example 1
Synthesis of phenyl B amidine hydrochloric acid salt
At 5 ℃～10 ℃, within the time of 4 hours, in the solution being formed by 117.8g (1.006 moles) benzyl cyanide and 55.8g (1.21 moles) dehydrated alcohol, introduce 44.6g (1.22 moles) hydrogen chloride gas.When by reaction soln at 4 ℃ standing 1 day and further at room temperature standing 2 days time, be settled out phenyl imido by ethyl acetate hydrochloride, it is white solid.
After the phenyl imido of collecting by filtration is crushed by ethyl acetate hydrochloride, the solution that portion-wise addition is comprised of 35.6g (2.09 moles) ammonia and 246g dehydrated alcohol wherein in jolting under ice-cooled.Then, ice-cooled, lower mixture is stirred 2 hours and further at room temperature spent the night.After white solid insoluble substance is filtered, under reduced pressure filtrate carried out to concentrate drying and obtain the phenylacetamidino hydrochloride of 172.5g (1.011 moles, yield is 100.5%), it is faint yellow molasse shape.
Reference example 2
Synthetic 2-is bromo-3 ', 4 '-dichloropropiophenone
At 62 ℃～65 ℃, within the time of 50 minutes, to by 3 of 45.8g (0.226 mole) ', in the solution that 4 '-dichloropropiophenone and 46g methyl alcohol form, drip 36g (0.2253 mole) bromine.After reaction soln is cooling, between 75g toluene and 91g water, described reaction soln is distributed.After utilizing water to wash toluene layer and being dried with magnesium sulfate, vapourisation under reduced pressure solvent, thereby obtain 64.3g (0.228 mole, yield is 101.1%) 2-bromo-3 ', 4 '-dichloropropiophenone, it is pistac oily.
Embodiment 1
Synthetic 2-phenmethyl-4-(3,4-dichlorophenyl)-5-Methylimidazole
At 50 ℃ to by 28.7g (0.168 mole) phenylacetamidino hydrochloride, 59g (0.427 mole) salt of wormwood and 210ml N, after suspension agitation that dinethylformamide forms 30 minutes, add wherein at the same temperature in batches 48.8g (0.173 mole) 2-bromo-3 ', 4 '-dichloropropiophenone, stirs other 4 hours subsequently at the same temperature.Then, after reaction suspension is cooling, between 800ml water and 300ml chloroform, it is distributed.Utilize water to chloroform layer washed twice after, vapourisation under reduced pressure chloroform, and by the molasse shape enriched material to making, add 150ml toluene and heating under stir and crystallize out.By filtration, collect the crystal of separating out, and after utilizing toluene wash, it is dried and obtains cream-colored powder.In acetonitrile, described powder is carried out to recrystallization, thereby obtain 18.8g (0.059 mole, yield is 35.3%) off-white powder shape crystal.
The fusing point of the crystal obtaining, the Rf value on thin-layer chromatography and 1h-NMR and mass-spectrometric data are as follows.
Fusing point: 158 ℃～161 ℃
TLC (silica gel, acetone): Rf=0.70
· 1H-NMR(CDCl 3)δ：2.28(s，3H)，3.94(s，2H)，7.12-7.66(m，7H)。
·MS?m/z(％)：316(M +，100)，301(3)，281(3)，239(4)，198(2)，171(4)，144(3)，122(9)，103(6)，91(8)，77(4)。
According to these spectroscopic datas, determine that the compound obtaining is 2-phenmethyl-4-(3,4-the dichlorophenyl)-5-Methylimidazole being expressed from the next.
Figure BPA00001328169100081
Embodiment 2
Synthetic 2-(2-chlorophenylmethyl)-4-(3,4-dichlorophenyl)-5-Methylimidazole
First, according to synthetic (2-chloro-phenyl-) B amidine hydrochloric acid salt of the method for reference example 1, wherein the benzyl cyanide with reference to example 1 changes (2-chloro-phenyl-) acetonitrile into.
Then, by implementing compound experiment according to the method for embodiment 1, obtain off-white powder shape crystal, wherein the phenylacetamidino hydrochloride of embodiment 1 is changed into (2-chloro-phenyl-) B amidine hydrochloric acid salt.
The fusing point of the crystal obtaining, the Rf value on thin-layer chromatography and 1h-NMR and mass-spectrometric data are as follows.
Fusing point: 150 ℃-152 ℃
TLC (silica gel, ethyl acetate): Rf=0.58
· 1H-NMR(d 6-DMSO)δ：2.38(s，3H)，4.09(s，2H)，7.27-7.80(m，7H)。
·MS?m/z(％)：350(M +，23)，315(100)，280(3)，171(2)，137(3)，122(10)，102(4)，89(3)。
According to these spectroscopic datas, determine that the compound obtaining is 2-(2-chlorophenylmethyl)-4-(3,4-the dichlorophenyl)-5-Methylimidazole being expressed from the next.
Figure BPA00001328169100091
Embodiment 3
Synthetic 2-(4-chlorophenylmethyl)-4-(3,4-dichlorophenyl)-5-Methylimidazole
First, according to synthetic (4-chloro-phenyl-) B amidine hydrochloric acid salt of the method for reference example 1, wherein the benzyl cyanide with reference to example 1 changes (4-chloro-phenyl-) acetonitrile into.
Then, by implementing compound experiment according to the method for embodiment 1, obtain the Powdered crystal of yellow-white, wherein the phenylacetamidino hydrochloride of embodiment 1 is changed into (4-chloro-phenyl-) B amidine hydrochloric acid salt.
The fusing point of the crystal obtaining, the Rf value on thin-layer chromatography and 1h-NMR and mass-spectrometric data are as follows.
Fusing point: 180 ℃-181 ℃
TLC (silica gel, acetone): Rf=0.72
· 1H-NMR(d 6-DMSO)δ：2.36(s，3H)，3.96(s，2H)，7.29-7.80(m，7H)。
·MS?m/z(％)：350(M +，100)，335(1)，315(14)，279(3)，190(3)，175(4)，164(4)，137(7)，125(10)，122(15)，102(8)，89(4)，75(3)。
According to these spectroscopic datas, determine that the compound obtaining is 2-(4-chlorophenylmethyl)-4-(3,4-the dichlorophenyl)-5-Methylimidazole being expressed from the next.
Figure BPA00001328169100101
Embodiment 4
Synthetic 2-(2,4 dichloro benzene methyl)-4-(3,4-dichlorophenyl)-5-Methylimidazole
First, according to synthetic (2,4 dichloro benzene base) B amidine hydrochloric acid salt of the method for reference example 1, wherein the benzyl cyanide with reference to example 1 changes (2,4 dichloro benzene base) acetonitrile into.
Then, by implementing compound experiment according to the method for embodiment 1, obtain white powder crystal, wherein the phenylacetamidino hydrochloride of embodiment 1 is changed into (2,4 dichloro benzene base) B amidine hydrochloric acid salt.
The fusing point of the crystal obtaining, the Rf value on thin-layer chromatography and 1h-NMR and mass-spectrometric data are as follows.
Fusing point: 117 ℃-119 ℃
TLC (silica gel, acetone): Rf=0.74
· 1H-NMR(d 6-DMSO)δ：2.36(s，3H)，4.07(s，2H)，7.33-7.77(m，7H)。
·MS?m/z(％)：386(M+2，100)，384(M +，31)，349(100)，299(3)，279(3)，193(4)，171(7)，159(9)，139(10)，121(6)，102(5)。
According to these spectroscopic datas, determine that the compound obtaining is 2-(2,4 dichloro benzene methyl)-4-(3,4-the dichlorophenyl)-5-Methylimidazole being expressed from the next.
Embodiment 5
Synthetic 2-(3,4-dichlorobenzene methyl)-4-(3,4-dichlorophenyl)-5-Methylimidazole
First, according to synthetic (3, the 4-dichlorophenyl) B amidine hydrochloric acid salt of the method for reference example 1, wherein the benzyl cyanide with reference to example 1 changes (3,4-dichlorophenyl) acetonitrile into.
Then, by implementing compound experiment according to the method for embodiment 1, obtain off-white powder shape crystal, wherein the phenylacetamidino hydrochloride of embodiment 1 is changed into (3,4-dichlorophenyl) B amidine hydrochloric acid salt.
The fusing point of the crystal obtaining, the Rf value on thin-layer chromatography and 1h-NMR and mass-spectrometric data are as follows.
Fusing point: 194 ℃-195 ℃
TLC (silica gel, acetone): Rf=0.67
· 1H-NMR(d 6-DMSO)δ：2.33(s，3H)，3.96(s，2H)，7.25-7.77(m，6H)。
·MS?m/z(％)：386(M+2，100)，384(M +，78)，371(1)，349(7)，314(9)，239(7)，212(3)，198(3)，171(7)，159(9)，139(10)，122(7)，102(4)，89(2)。
According to these spectroscopic datas, determine that the compound obtaining is 2-(3,4-dichlorobenzene methyl)-4-(3,4-the dichlorophenyl)-5-Methylimidazole being expressed from the next.
Figure BPA00001328169100121
Embodiment 6
Synthetic 2-(4-Brombenzyl)-4-(3,4-dichlorophenyl)-5-Methylimidazole
First, according to synthetic (4-bromophenyl) B amidine hydrochloric acid salt of the method for reference example 1, wherein the benzyl cyanide with reference to example 1 changes (4-bromophenyl) acetonitrile into.
Then, by implementing compound experiment according to the method for embodiment 1, obtain white powder crystal, wherein the phenylacetamidino hydrochloride of embodiment 1 is changed into (4-bromophenyl) B amidine hydrochloric acid salt.
The fusing point of the crystal obtaining, the Rf value on thin-layer chromatography and 1h-NMR and mass-spectrometric data are as follows.
Fusing point: 207 ℃-208 ℃
TLC (silica gel, hexane: ethyl acetate=1: 1): Rf=0.43
· 1H-NMR(d 6-DMSO)δ：2.07(s，3H)，3.92(s，2H)，7.21-7.78(m，7H)。
·MS?m/z(％)：398(M+4，46)，396(M+2，100)，394(M +，62)，361(2)，315(11)，299(3)，279(3)，239(4)，198(5)，183(3)，171(10)，140(8)，122(20)，102(14)，89(6)，75(3)。
According to these spectroscopic datas, determine that the compound obtaining is 2-(4-Brombenzyl)-4-(3,4-the dichlorophenyl)-5-Methylimidazole being expressed from the next.
Figure BPA00001328169100131
Embodiment 7
Prepared surface treatment liquid, described surface treatment liquid contains various imidazolium compoundss synthetic in embodiment 1～6, and except these compounds, also contains 2-phenylimidazole as effective constituent.By making various treatment solutions contact and form chemical films and measure the wetting time of fusion welding to copper on copper surface with copper, thereby measure the antioxidant property to the copper surface that wherein imidazolium compounds works.Can conclude in this case, wetting time is shorter, and the antioxidant property of imidazolium compounds is more excellent.
The details of evaluation test is as follows.
(1) prepare surface treatment liquid
In being dissolved in to ion exchanged water, imidazolium compounds, acid, metal-salt and halogen compounds with after forming described in acquisition table 1, utilize ammoniacal liquor to regulate to prepare surface treatment liquid to pH.
(2) surface treatment method:
The test film that is metallic copper to material (being of a size of the copper coin of 5mm * 50mm * 0.3mm) carries out degreasing, then carries out soft erosion.In test film being immersed to surface treatment liquid under preset temperature, also continue the scheduled time, thereby form chemical films on copper surface after, utilize water that test film is washed and is dried.
(3) measure wetting time
To experience surface-treated test film and immerse rear fusing assistant (post flux) [trade(brand)name: " JS-64MSS ", (the Koki Co. of You Hong brightness Co., Ltd., Ltd.) manufacture] in and by solder tester [Co., Ltd. of SAT-2000 ，You Lishi section (Rhesca Corporation) manufacture], the wetting time of scolder (second) is measured.Scolder used is tin-plumbous eutectic solder (trade(brand)name: H63A, by Senju Metal Industry Co., Ltd (Senju Metal Industry Co., Ltd), manufactured) and measuring condition as follows: welding temperature is that 240 ℃, impregnating depth are that 2mm, impregnating speed are 16mm/ second.
In this connection, test film after indoor standing 96 hours of the fixed temperature and humidity of 40 ℃ of temperature and 90%RH humidity of the test film that the test film of scolder wetting time being measured is moment after (A) surface treatment, (B) and (C) test film further heat 10 minutes at 200 ℃ after.
The test-results of acquisition is shown in Table 1.
Figure BPA00001328169100151
According to the test-results shown in table 1, owing to containing 2-phenmethyl-4-(3 of the present invention, 4-dichlorophenyl)-5-methylimidazole compound can form the chemical films of wet fastness and excellent heat resistance as the surface treatment liquid of effective constituent on copper surface, thus can be by them the oxidation-resistance for copper surface.
Industrial applicibility
According to the present invention, 2-phenmethyl-4-(3 can be provided, 4-dichlorophenyl)-5-methylimidazole compound, it can be used as the surperficial antioxidant of metal, particularly copper (comprising copper alloy) and solidifying agent or the curing catalyst of epoxy resin, and also can be used as the intermediate raw material in medicine and pesticide field.
Although the present invention is had been described in detail with reference to the specific embodiment of the present invention, it will be apparent to those skilled in the art that in the situation that not deviating from its scope, can carry out therein variations and modifications.
The application be take the Japanese patent application 2008-225632 submitting on September 3rd, 2008, Japanese patent application 2009-130022 that on May 29th, 2009 submits to and the Japanese patent application 2009-140655 that submits on June 12nd, 2009 is basis, hereby by reference to its complete content is incorporated herein.

Claims (1)

1. 2-phenmethyl-4-(3,4-the dichlorophenyl)-5-methylimidazole compound being represented by formula (I):
Figure FPA00001328169000011
X wherein 1and X 2identical or different and represent hydrogen atom, chlorine atom or bromine atoms.
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EP0627499A1 (en) * 1993-05-10 1994-12-07 Shikoku Chemicals Corporation Agent for treating surfaces of copper and copper alloys
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