WO2010027077A1 - Composé de 2-benzyl-4-(3,4-dichlorophényl)-5-méthylimidazole - Google Patents

Composé de 2-benzyl-4-(3,4-dichlorophényl)-5-méthylimidazole Download PDF

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Publication number
WO2010027077A1
WO2010027077A1 PCT/JP2009/065616 JP2009065616W WO2010027077A1 WO 2010027077 A1 WO2010027077 A1 WO 2010027077A1 JP 2009065616 W JP2009065616 W JP 2009065616W WO 2010027077 A1 WO2010027077 A1 WO 2010027077A1
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WO
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Prior art keywords
dichlorophenyl
methylimidazole
compound
hydrochloride
benzyl
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PCT/JP2009/065616
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English (en)
Inventor
Takayuki Murai
Hirohiko Hirao
Koji Takasaku
Masayuki Miyazaki
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Shikoku Chemicals Corporation
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Publication date
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Priority to CN200980134515.8A priority Critical patent/CN102144046B/zh
Publication of WO2010027077A1 publication Critical patent/WO2010027077A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
    • C23F11/14—Nitrogen-containing compounds
    • C23F11/149—Heterocyclic compounds containing nitrogen as hetero atom
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
    • B23K—SOLDERING OR UNSOLDERING; WELDING; CLADDING OR PLATING BY SOLDERING OR WELDING; CUTTING BY APPLYING HEAT LOCALLY, e.g. FLAME CUTTING; WORKING BY LASER BEAM
    • B23K1/00—Soldering, e.g. brazing, or unsoldering
    • B23K1/20—Preliminary treatment of work or areas to be soldered, e.g. in respect of a galvanic coating
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
    • B23K—SOLDERING OR UNSOLDERING; WELDING; CLADDING OR PLATING BY SOLDERING OR WELDING; CUTTING BY APPLYING HEAT LOCALLY, e.g. FLAME CUTTING; WORKING BY LASER BEAM
    • B23K35/00—Rods, electrodes, materials, or media, for use in soldering, welding, or cutting
    • B23K35/22—Rods, electrodes, materials, or media, for use in soldering, welding, or cutting characterised by the composition or nature of the material
    • B23K35/36—Selection of non-metallic compositions, e.g. coatings, fluxes; Selection of soldering or welding materials, conjoint with selection of non-metallic compositions, both selections being of interest
    • B23K35/3612—Selection of non-metallic compositions, e.g. coatings, fluxes; Selection of soldering or welding materials, conjoint with selection of non-metallic compositions, both selections being of interest with organic compounds as principal constituents
    • B23K35/3615—N-compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C22/00—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals
    • C23C22/05—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using aqueous solutions
    • C23C22/06—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using aqueous solutions using aqueous acidic solutions with pH less than 6
    • C23C22/48—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using aqueous solutions using aqueous acidic solutions with pH less than 6 not containing phosphates, hexavalent chromium compounds, fluorides or complex fluorides, molybdates, tungstates, vanadates or oxalates
    • C23C22/52—Treatment of copper or alloys based thereon
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
    • C23F11/14—Nitrogen-containing compounds
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/22—Secondary treatment of printed circuits
    • H05K3/28—Applying non-metallic protective coatings
    • H05K3/282—Applying non-metallic protective coatings for inhibiting the corrosion of the circuit, e.g. for preserving the solderability

Definitions

  • the present invention relates to a novel 2-benzyl- 4- (3 , 4-dichlorophen ⁇ l) -5-methylimidazole compound.
  • an imidazole compound similar to the compound of the invention for example, 2- (2 , 4-dichloro-benzyl) -5- (3 , 4 -dichloro-phenyl) -lH-imidazole is disclosed in Patent Document 1.
  • an imidazole compound wherein a methyl group is bonded to the 4 (5) - position of the imidazole ring is not disclosed.
  • An object of the invention is to provide a novel 2- benzyl-4- (3,4-dichlorophenyl) -5-methylimidazole compound.
  • the present inventors made extensive and intensive investigations. As a result, the present inventors have found that a novel 2-benz ⁇ l-4- (3,4-dichlorophenyl) -5- methylimidazole compound represented by the formula (I) can be synthesized and thus they have accomplished the invention.
  • Xi and X2 are the same or different and represent a hydrogen atom, a chlorine atom, or a bromine atom.
  • the 2-benzyl-4- (3,4-dichlorophenyl) -5- methylimidazole compound of the invention is useful as an antioxidant for the surface of a metal, particularly a copper (including a copper alloy) and a curing agent or a curing accelerator of an epoxy resin and also as an intermediate raw material in medicinal and agricultural chemical fields.
  • the 2-benzyl-4- (3,4-dichlorophenyl) -5- methylimidazole compound of the invention is one represented by the following formula (I) and examples thereof include:
  • Xi and X2 are the same or different and represent a hydrogen atom, a chlorine atom, or a bromine atom.
  • the 2-benzyl-4- (3,4-dichlorophenyl) -5- methylimidazole compound of the invention can be synthesized in accordance with known methods. For example, as shown in the following reaction scheme, 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.
  • Xi and X 2 are the same as described above and X3 represents a chlorine atom, a bromine atom, or an iodine atom.
  • the amount of the arylacetamidine compound to be used is preferably in a ratio of 0.8 to 1.5 times moles , more preferably 0.9 to 1.1 times moles relative to the 2-halogenated 3 ',4'- dichloropropiophenone compound.
  • the amount of the dehydrohalogenating agent to be used is preferably in a ratio of 1 to 10 times equivalents relative to the 2- halogenated 3 ' , 4 ' -dichloropropiophenone compound.
  • 2-halogenated 3 ',4'- dichloropropiophenone compound there may be mentioned 2- chloro-3 ', 4 ' -dichloropropiophenone, 2-bromo-3 ' ,4 ' - dichloropropiophenone, and 2-iodo-3 ' ,4 ' - dichloropropiophenone .
  • the 2-halogenated 3' ,4 ' -dichloropropiophenone compound is obtained by halogenating the 2-position of 3 ' ,4 ' -dichloropropiophenone.
  • halogenation chlorination or iodination is also possible but a bromination reaction wherein an equimolar amount of bromine is reacted with 3 ' ,4 ' -dichloropropiophenone is most simple and convenient.
  • 3 ' ,4 ' -dichloropropiophenone a commercially available one as a reagent can be used.
  • the above arylacetamidine compound can be obtained by reacting an arylacetamidine hydrochloride with an alkali agent and removing hydrogen chloride.
  • an arylacetamidine hydrochloride or a salt of the arylacetamidine compound with a conventionally known inorganic acid or organic acid instead of the arylacetamidine compound.
  • the arylacetamidine hydrochloride can be synthesized in accordance with known methods.
  • the arylacetamidine hydrochloride can be synthesized by reacting a benzyl cyanide compound with hydrogen chloride gas and a lower alcohol such as ethanol to effect conversion into an arylacetimidate hydrochloride and further reacting it with ammonia.
  • hydrochloride of the arylacetamidine compound obtained through such reactions examples include: phenylacetamidine hydrochloride, (2-chlorophenyl ) acetamidine hydrochloride , (3-chlorophenyl) acetamidine hydrochloride, (4 -chlorophenyl ) acetamidine hydrochloride , (2 ,3-dichlorophenyl) acetamidine hydrochloride, (2 , 4 -dichlorophenyl) acetamidine hydrochloride, (2 , 5-dichlorophenyl) acetamidine hydrochloride , (2 , 6-dichlorophenyl) acetamidine hydrochloride , (3, 4 -dichlorophenyl) acetamidine hydrochloride, (3, 5-dichlorophenyl) acetamidine hydrochloride, (2-bromophenyl) acetamidine hydrochloride , (3-bro
  • any known one can be used without limitation.
  • examples of such a dehydrohalogenating agent include inorganic alkali compounds such as sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, and potassium bicarbonate; organic base compounds such as triethylamine and 1,8- diazabicyclo [5.4.0] -7-undecene (DBU); metal alkoxide compounds such as sodium methoxide and potassium tert- butoxide; and the like.
  • inorganic alkali compounds such as sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, and potassium bicarbonate
  • organic base compounds such as triethylamine and 1,8- diazabicyclo [5.4.0] -7-undecene (DBU)
  • metal alkoxide compounds such as sodium methoxide and potassium tert- butoxide; and the like.
  • any known one can be used without limitation as long as it can dissolve the 2- halogenated 3 ' ,4 ' -dichloropropiophenone compound and the arylacetamidine compound and is not involved in the reactions.
  • a solvent include alcohols such as isopropyl alcohol and tert-butanol ; hydrocarbons such as hexane and toluene; halogenated hydrocarbons such as chloroform and chlorobenzene ; esters such as ethyl acetate; nitriles such as acetonitrile; ethers such as tetrahydrofuran , dioxane, and ethylene glycol dimethyl ether; amides such as N,N-dimeth ⁇ lformamide (DMF) and N,N-dimethylacetamide (DMAC) ; dimethyl sulfoxide (DMSO) ; and the like. These solvents may be used in combination.
  • the reaction temperature is preferably from room temperature to refluxing temperature and the reaction time is preferably from 1 to 10 hours.
  • the reaction may be usually carried out under atmospheric pressure.
  • the 2-benzyl-4- (3,4-dichlorophenyl) -5- methylimidazole compound formed under the above reaction conditions can be isolated by usual post-treatment.
  • a crude product of the compound can be obtained by partitioning the reaction mixture after completion of the reaction between an aqueous layer and an organic solvent layer and evaporating the organic solvent after washing the organic solvent layer with water, and the crude product can be further purified by recrystallization operation or the like.
  • Reference Examples 1 and 2 show synthesis examples of phenylacetamidine hydrochloride and 2-bromo-3 ' , 4 ' -dichloropropiophenone , respectively .
  • Reference Example 1 (Synthesis of phenylacetamidine hydrochloride)
  • chloroform was evaporated under reduced pressure and crystals were precipitated by adding 150 ml of toluene to the resulting thick syrup-form concentrate and stirring under heating. The precipitated crystals were collected by filtration and, after washing with toluene, were dried to obtain a cream-colored powder. The powder was recrystallized from acetonitrile to obtain 18.8 g (0.059 mol , yield 35.3%) of milky white powdery crystals.
  • Reference Example 1 changing phenylacetonitrile of Reference Example 1 to (2-chlorophenyl) acetonitrile.
  • milky white powdery crystals were obtained by carrying out a synthesis experiment in accordance with the method of Example 1, changing phenylacetamidine hydrochloride of Example 1 to (2-chlorophenyl) acetamidine hydrochloride .
  • (4-chlorophenyl) acetamidine hydrochloride was synthesized in accordance with the method of Reference Example 1, changing phenylacetonitrile of Reference Example 1 to (4-chlorophenyl) acetonitrile.
  • yellowish white powdery crystals were obtained by carrying out a synthesis experiment in accordance with the method of Example 1, changing phenylacetamidine hydrochloride of Example 1 to (4- chlorophenyl ) acetarnidine hydrochloride .
  • Melting point, Rf value on thin layer chromatography, and 1 H-NMR and mass spectral data of the obtained crystals were as follows.
  • milky white powdery crystals were obtained by carrying out a synthesis experiment in accordance with the method of Example 1, changing phenylacetamidine hydrochloride of Example 1 to (3,4- dichlorophenyl) acetamidine hydrochloride.
  • (4-bromophenyl) acetamidine hydrochloride was synthesized in accordance with the method of Reference Example 1, changing phenylacetonitrile of Reference Example 1 to (4-bromophenyl) acetonitrile.
  • test piece whose material is metallic copper (a copper plate having a size of 5 mm x 50 mm x 0.3 mm) was degreased and then subjected to soft etching. After the test piece was immersed in a surface treating liquid at a predetermined temperature for a predetermined time to form a chemical film on the surface of copper, the test piece was washed with water and dried.
  • the test piece subjected to the surface treatment was immersed in a post flux [trade name "JS-64MSS” manufactured by Koki Co., Ltd.] and solder wetting time (sec) was measured by a solder wetting tester (SAT-2000, manufactured by Rhesca Corporation) .
  • the solder used was a tin-lead eutectic solder (trade name: H63A, manufactured by Senju Metal Industry Co. , Ltd.) and the measurement conditions were as follows: soldering temperature 240 0 C, immersion depth 2 mm, immersion speed 16 mm/sec.
  • test pieces on which the solder wetting time was measured were (A) one immediately after the surface treatment, (B) one after allowed to stand in a constant-temperature constant-humidity chamber at a temperature of 40 0 C and a humidity of 90% RH for 96 hours, and (C) one after further heated at 200 0 C for 10 minutes .
  • the obtained test results were as shown in Table 1.
  • the surface treating liquids containing a 2-benzyl- 4- (3,4-dichlorophen ⁇ l) -5-methyli ⁇ idazole compound of the invention as an effective ingredient can form a chemical film excellent in moisture resistance and heat resistance on the surface of copper, they are useful for antioxidation of copper surface.
  • the 2-benzyl-4- (3,4- dichlorophen ⁇ l) -5-methylimidazole compound which is useful as an antioxidant for the surface of a metal , particularly copper (including a copper alloy) and a curing agent or a curing accelerator of an epoxy resin and also as an intermediate raw material in medicinal and agricultural chemical fields can be provided.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Materials Engineering (AREA)
  • Metallurgy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Chemical Treatment Of Metals (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un composé de 2-benzyl-4-(3,4-dichlorophényl)-5-méthylimidazole utile en tant qu'antioxydant pour une surface en cuivre, un agent de durcissement pour des résines époxy, ou un intermédiaire pour des médicaments et des produits chimiques agricoles. L'invention concerne un composé de 2-benzyl-4-(3,4-dichlorophényl)-5-méthylimidazole représenté par la formule (I). Le composé peut être synthétisé par réaction d'un composé de 3',4'-dichloropropiophénone 2-halogéné avec un composé d'arylacétamidine sous chauffage en présence d'un agent de déshydrohalogénation dans un solvant organique. Dans la formule (I), X1 et X2 sont identiques ou différents et représentent un atome d'hydrogène, un atome de chlore ou un atome de brome.
PCT/JP2009/065616 2008-09-03 2009-09-02 Composé de 2-benzyl-4-(3,4-dichlorophényl)-5-méthylimidazole WO2010027077A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN200980134515.8A CN102144046B (zh) 2008-09-03 2009-09-02 2-苯甲基-4-(3，4-二氯苯基)-5-甲基咪唑化合物

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP2008-225632 2008-09-03
JP2008225632 2008-09-03
JP2009130022 2009-05-29
JP2009-130022 2009-05-29
JP2009140655A JP5484795B2 (ja) 2008-09-03 2009-06-12 ２−ベンジル−４−（３，４−ジクロロフェニル）−５−メチルイミダゾール化合物
JP2009-140655 2009-06-12

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WO2010027077A1 true WO2010027077A1 (fr) 2010-03-11

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JP (1) JP5484795B2 (fr)
KR (1) KR101602978B1 (fr)
CN (1) CN102144046B (fr)
MY (1) MY158638A (fr)
TW (1) TWI507395B (fr)
WO (1) WO2010027077A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010070530A (ja) * 2008-09-22 2010-04-02 Shikoku Chem Corp ２−（２，４−ジクロロベンジル）−４−（ハロゲン化フェニル）イミダゾール化合物

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5260367B2 (ja) * 2008-09-26 2013-08-14 四国化成工業株式会社 ２−（クロロベンジル）−４−フェニルイミダゾール化合物
JP5615227B2 (ja) * 2011-05-23 2014-10-29 四国化成工業株式会社 銅または銅合金の表面処理剤及びその利用
JP5615233B2 (ja) * 2011-06-20 2014-10-29 四国化成工業株式会社 銅または銅合金の表面処理剤及びその利用

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JPH06322551A (ja) * 1993-05-10 1994-11-22 Shikoku Chem Corp 銅及び銅合金の表面処理剤
JPH06329635A (ja) * 1993-05-24 1994-11-29 Shikoku Chem Corp 新規イミダゾール化合物
EP0627499A1 (fr) * 1993-05-10 1994-12-07 Shikoku Chemicals Corporation Agent de traitement de surfaces en cuivre ou ses alliages
JPH07243054A (ja) * 1994-03-08 1995-09-19 Shikoku Chem Corp 銅及び銅合金の表面処理剤
WO2000071120A1 (fr) * 1999-05-25 2000-11-30 Smithkline Beecham Corporation Composes antibacteriens

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Publication number Priority date Publication date Assignee Title
US7661577B2 (en) * 2003-03-19 2010-02-16 Shikoku Chemicals Corporation Imidazole compound and use thereof

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06322551A (ja) * 1993-05-10 1994-11-22 Shikoku Chem Corp 銅及び銅合金の表面処理剤
EP0627499A1 (fr) * 1993-05-10 1994-12-07 Shikoku Chemicals Corporation Agent de traitement de surfaces en cuivre ou ses alliages
US5560785A (en) * 1993-05-10 1996-10-01 Shikoku Chemicals Corporation Method for forming a protective chemical layer on copper and copper alloy surfaces
JPH06329635A (ja) * 1993-05-24 1994-11-29 Shikoku Chem Corp 新規イミダゾール化合物
JPH07243054A (ja) * 1994-03-08 1995-09-19 Shikoku Chem Corp 銅及び銅合金の表面処理剤
WO2000071120A1 (fr) * 1999-05-25 2000-11-30 Smithkline Beecham Corporation Composes antibacteriens

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010070530A (ja) * 2008-09-22 2010-04-02 Shikoku Chem Corp ２−（２，４−ジクロロベンジル）−４−（ハロゲン化フェニル）イミダゾール化合物

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JP2011006323A (ja) 2011-01-13
KR20110050663A (ko) 2011-05-16
KR101602978B1 (ko) 2016-03-11
TW201010982A (en) 2010-03-16
TWI507395B (zh) 2015-11-11
CN102144046B (zh) 2014-02-26
JP5484795B2 (ja) 2014-05-07
CN102144046A (zh) 2011-08-03
MY158638A (en) 2016-10-31

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