JPH05263275A - ベンゾイミダゾール系化合物ならびにそれを用いた銅および銅合金の表面処理剤 - Google Patents
ベンゾイミダゾール系化合物ならびにそれを用いた銅および銅合金の表面処理剤Info
- Publication number
- JPH05263275A JPH05263275A JP5015873A JP1587393A JPH05263275A JP H05263275 A JPH05263275 A JP H05263275A JP 5015873 A JP5015873 A JP 5015873A JP 1587393 A JP1587393 A JP 1587393A JP H05263275 A JPH05263275 A JP H05263275A
- Authority
- JP
- Japan
- Prior art keywords
- copper
- benzimidazole
- acid
- compound
- treating agent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 229910052802 copper Inorganic materials 0.000 title claims abstract description 18
- 239000010949 copper Substances 0.000 title claims abstract description 18
- 229910000881 Cu alloy Inorganic materials 0.000 title claims abstract description 12
- 150000001875 compounds Chemical class 0.000 title claims description 9
- 239000003795 chemical substances by application Substances 0.000 title abstract description 10
- -1 benzimidazole compound Chemical class 0.000 claims description 22
- 239000012756 surface treatment agent Substances 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 5
- 125000002947 alkylene group Chemical group 0.000 abstract description 3
- 125000005843 halogen group Chemical group 0.000 abstract description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- 239000000243 solution Substances 0.000 description 8
- 229910000679 solder Inorganic materials 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 235000011054 acetic acid Nutrition 0.000 description 5
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 5
- 230000004907 flux Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 4
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000003884 phenylalkyl group Chemical group 0.000 description 4
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000007598 dipping method Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- LDZYRENCLPUXAX-UHFFFAOYSA-N 2-methyl-1h-benzimidazole Chemical compound C1=CC=C2NC(C)=NC2=C1 LDZYRENCLPUXAX-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 229960003280 cupric chloride Drugs 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- RBNPOMFGQQGHHO-UHFFFAOYSA-N -2,3-Dihydroxypropanoic acid Natural products OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- PGULAETZYHZJSS-UHFFFAOYSA-N 2-(2-phenylpropyl)-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1CC(C)C1=CC=CC=C1 PGULAETZYHZJSS-UHFFFAOYSA-N 0.000 description 1
- ZJWHYIXFXKGCTR-UHFFFAOYSA-N 2-(3-phenylbutyl)-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1CCC(C)C1=CC=CC=C1 ZJWHYIXFXKGCTR-UHFFFAOYSA-N 0.000 description 1
- UNFZYVZRIDSAOD-UHFFFAOYSA-N 2-(3-phenylpropyl)-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1CCCC1=CC=CC=C1 UNFZYVZRIDSAOD-UHFFFAOYSA-N 0.000 description 1
- FJYCZGSNCTXPJX-UHFFFAOYSA-N 2-(4-phenylbutyl)-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1CCCCC1=CC=CC=C1 FJYCZGSNCTXPJX-UHFFFAOYSA-N 0.000 description 1
- CNBHHZNFXSUXBH-UHFFFAOYSA-N 2-(5-phenylpentyl)-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1CCCCCC1=CC=CC=C1 CNBHHZNFXSUXBH-UHFFFAOYSA-N 0.000 description 1
- IZOYZHUSMHLHTQ-UHFFFAOYSA-N 2-(8-phenyloctyl)-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1CCCCCCCCC1=CC=CC=C1 IZOYZHUSMHLHTQ-UHFFFAOYSA-N 0.000 description 1
- VABCHWJQYURQOY-UHFFFAOYSA-N 2-(9-phenylnonyl)-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1CCCCCCCCCC1=CC=CC=C1 VABCHWJQYURQOY-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- KDPLHXSCHYOOMP-UHFFFAOYSA-N 2-benzyl-6-ethyl-1h-benzimidazole Chemical compound N1C2=CC(CC)=CC=C2N=C1CC1=CC=CC=C1 KDPLHXSCHYOOMP-UHFFFAOYSA-N 0.000 description 1
- BEDBENSICYHSIA-UHFFFAOYSA-N 2-benzyl-6-methyl-1h-benzimidazole Chemical compound N1C2=CC(C)=CC=C2N=C1CC1=CC=CC=C1 BEDBENSICYHSIA-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- NYGDMPXFJMTHTG-UHFFFAOYSA-N 4-ethyl-1h-benzimidazole Chemical compound CCC1=CC=CC2=C1N=CN2 NYGDMPXFJMTHTG-UHFFFAOYSA-N 0.000 description 1
- JRTIGUGQHJAIIZ-UHFFFAOYSA-N 4-ethyl-2-(3-phenylpropyl)-1h-benzimidazole Chemical compound N1C=2C(CC)=CC=CC=2N=C1CCCC1=CC=CC=C1 JRTIGUGQHJAIIZ-UHFFFAOYSA-N 0.000 description 1
- SMQCSUCNYHMNPT-UHFFFAOYSA-N 4-ethyl-2-[3-(3-methylphenyl)propyl]-1h-benzimidazole Chemical compound N=1C=2C(CC)=CC=CC=2NC=1CCCC1=CC=CC(C)=C1 SMQCSUCNYHMNPT-UHFFFAOYSA-N 0.000 description 1
- QCXGJTGMGJOYDP-UHFFFAOYSA-N 4-methyl-1h-benzimidazole Chemical compound CC1=CC=CC2=C1N=CN2 QCXGJTGMGJOYDP-UHFFFAOYSA-N 0.000 description 1
- RWXZXCZBMQPOBF-UHFFFAOYSA-N 5-methyl-1H-benzimidazole Chemical compound CC1=CC=C2N=CNC2=C1 RWXZXCZBMQPOBF-UHFFFAOYSA-N 0.000 description 1
- QMJJWAQRQFYHHM-UHFFFAOYSA-N 6-ethyl-2-(2-phenylethyl)-1h-benzimidazole Chemical compound N1C2=CC(CC)=CC=C2N=C1CCC1=CC=CC=C1 QMJJWAQRQFYHHM-UHFFFAOYSA-N 0.000 description 1
- HAYXBUBXIMNIOR-UHFFFAOYSA-N 6-methyl-2-(2-phenylethyl)-1h-benzimidazole Chemical compound N1C2=CC(C)=CC=C2N=C1CCC1=CC=CC=C1 HAYXBUBXIMNIOR-UHFFFAOYSA-N 0.000 description 1
- UTRPQXISVOJOQP-UHFFFAOYSA-N 6-methyl-2-(2-phenylpropyl)-1h-benzimidazole Chemical compound N=1C2=CC=C(C)C=C2NC=1CC(C)C1=CC=CC=C1 UTRPQXISVOJOQP-UHFFFAOYSA-N 0.000 description 1
- OTSDDKXNUZKLTB-UHFFFAOYSA-N 6-methyl-2-(4-phenylbutyl)-1h-benzimidazole Chemical compound N1C2=CC(C)=CC=C2N=C1CCCCC1=CC=CC=C1 OTSDDKXNUZKLTB-UHFFFAOYSA-N 0.000 description 1
- FJMISRBWPLKKRY-UHFFFAOYSA-N 6-methyl-2-[2-(2-methylphenyl)ethyl]-1h-benzimidazole Chemical compound N1C2=CC(C)=CC=C2N=C1CCC1=CC=CC=C1C FJMISRBWPLKKRY-UHFFFAOYSA-N 0.000 description 1
- BFAZABQTQHGQMF-UHFFFAOYSA-N 6-methyl-2-[3-(2-methylphenyl)propyl]-1h-benzimidazole Chemical compound N1C2=CC(C)=CC=C2N=C1CCCC1=CC=CC=C1C BFAZABQTQHGQMF-UHFFFAOYSA-N 0.000 description 1
- TUTVDOPAKOUNQV-UHFFFAOYSA-N 6-methyl-2-phenyl-1h-benzimidazole Chemical compound N1C2=CC(C)=CC=C2N=C1C1=CC=CC=C1 TUTVDOPAKOUNQV-UHFFFAOYSA-N 0.000 description 1
- JTXZPQIXIXYMDY-UHFFFAOYSA-N 6-phenylhexanoic acid Chemical compound OC(=O)CCCCCC1=CC=CC=C1 JTXZPQIXIXYMDY-UHFFFAOYSA-N 0.000 description 1
- VVVYAAPBIUJKCE-UHFFFAOYSA-N CC1=CC=CCC1(C)CCC1=NC2=CC=C(C)C=C2N1 Chemical compound CC1=CC=CCC1(C)CCC1=NC2=CC=C(C)C=C2N1 VVVYAAPBIUJKCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RBNPOMFGQQGHHO-UWTATZPHSA-N D-glyceric acid Chemical compound OC[C@@H](O)C(O)=O RBNPOMFGQQGHHO-UWTATZPHSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- YHOBNVSNVRLECD-UHFFFAOYSA-N N1C2=CC(CC)=CC=C2N=C1CCCC1(C)CC=CC=C1C Chemical compound N1C2=CC(CC)=CC=C2N=C1CCCC1(C)CC=CC=C1C YHOBNVSNVRLECD-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 239000005083 Zinc sulfide Substances 0.000 description 1
- RAOSIAYCXKBGFE-UHFFFAOYSA-K [Cu+3].[O-]P([O-])([O-])=O Chemical compound [Cu+3].[O-]P([O-])([O-])=O RAOSIAYCXKBGFE-UHFFFAOYSA-K 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- YTLQFZVCLXFFRK-UHFFFAOYSA-N bendazol Chemical compound N=1C2=CC=CC=C2NC=1CC1=CC=CC=C1 YTLQFZVCLXFFRK-UHFFFAOYSA-N 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- YTIVTFGABIZHHX-UHFFFAOYSA-N butynedioic acid Chemical compound OC(=O)C#CC(O)=O YTIVTFGABIZHHX-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940116318 copper carbonate Drugs 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-IHWYPQMZSA-N isocrotonic acid Chemical compound C\C=C/C(O)=O LDHQCZJRKDOVOX-IHWYPQMZSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- KTWYXPPIGPDVCF-UHFFFAOYSA-N phosphoric acid;zinc Chemical compound [Zn].OP(O)(O)=O.OP(O)(O)=O KTWYXPPIGPDVCF-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
-
- 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
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Chemical Treatment Of Metals (AREA)
- Non-Metallic Protective Coatings For Printed Circuits (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1841592 | 1992-01-08 | ||
| JP4-18415 | 1992-01-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH05263275A true JPH05263275A (ja) | 1993-10-12 |
Family
ID=11971030
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5015873A Pending JPH05263275A (ja) | 1992-01-08 | 1993-01-06 | ベンゾイミダゾール系化合物ならびにそれを用いた銅および銅合金の表面処理剤 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US5435860A (en, 2012) |
| EP (1) | EP0551112B1 (en, 2012) |
| JP (1) | JPH05263275A (en, 2012) |
| KR (1) | KR100263516B1 (en, 2012) |
| DE (1) | DE69302021T2 (en, 2012) |
| SG (1) | SG52429A1 (en, 2012) |
| TW (1) | TW217426B (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07142846A (ja) * | 1993-11-17 | 1995-06-02 | Nec Corp | 印刷配線板の製造方法 |
| JPH08148811A (ja) * | 1994-11-22 | 1996-06-07 | Nec Toyama Ltd | プリント配線板の製造方法 |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW263534B (en, 2012) * | 1993-08-11 | 1995-11-21 | Makkusu Kk | |
| US5735973A (en) * | 1993-12-20 | 1998-04-07 | Tamura Kaken Corporation | Printed circuit board surface protective agent |
| JP2781954B2 (ja) * | 1994-03-04 | 1998-07-30 | メック株式会社 | 銅および銅合金の表面処理剤 |
| JP3329572B2 (ja) * | 1994-04-15 | 2002-09-30 | 福田金属箔粉工業株式会社 | 印刷回路用銅箔およびその表面処理方法 |
| JP2550915B2 (ja) * | 1994-06-21 | 1996-11-06 | 日本電気株式会社 | 印刷配線板の表面保護剤および表面保護膜の形成方法 |
| DE4444388A1 (de) * | 1994-11-28 | 1996-05-30 | Atotech Deutschland Gmbh | Verfahren zum Bonden von Drähten auf oxidationsempfindlichen, lötbaren Metallsubstraten |
| JP2923524B2 (ja) * | 1995-08-01 | 1999-07-26 | メック株式会社 | 銅および銅合金のマイクロエッチング剤並びにマイクロエッチング方法 |
| JP3547028B2 (ja) * | 1996-02-26 | 2004-07-28 | 四国化成工業株式会社 | 銅及び銅合金の表面処理剤 |
| GB2331999B (en) * | 1997-10-28 | 2003-01-22 | Ibm | Copper preservative treatment |
| GB2336378A (en) | 1998-04-17 | 1999-10-20 | Ibm | Protective treatment of a zinc or zinc alloy surface with an alcoholic solution of an azole |
| US6524644B1 (en) | 1999-08-26 | 2003-02-25 | Enthone Inc. | Process for selective deposition of OSP coating on copper, excluding deposition on gold |
| JP2003031929A (ja) * | 2001-07-19 | 2003-01-31 | Tamura Kaken Co Ltd | 水溶性プリフラックス、プリント回路基板及びプリント回路基板の金属の表面処理方法 |
| US7232478B2 (en) * | 2003-07-14 | 2007-06-19 | Enthone Inc. | Adhesion promotion in printed circuit boards |
| JP3952410B2 (ja) * | 2004-02-10 | 2007-08-01 | タムラ化研株式会社 | 金属の表面処理剤、プリント回路基板およびプリント回路基板の金属の表面処理方法 |
| US7794531B2 (en) * | 2007-01-08 | 2010-09-14 | Enthone Inc. | Organic solderability preservative comprising high boiling temperature alcohol |
| WO2011147448A1 (en) | 2010-05-26 | 2011-12-01 | Atotech Deutschland Gmbh | Composition and method for micro etching of copper and copper alloys |
| CN102432542B (zh) * | 2011-09-09 | 2014-04-09 | 深圳市板明科技有限公司 | 咪唑化合物及其制备方法和应用、有机防焊保护剂 |
| US10052310B2 (en) | 2013-10-18 | 2018-08-21 | Baylor College Of Medicine | Separase inhibitors and uses thereof |
| WO2015058185A1 (en) * | 2013-10-18 | 2015-04-23 | Baylor College Of Medicine | Separase inhibitors and uses thereof |
| KR101663112B1 (ko) * | 2014-01-13 | 2016-10-06 | (주)켐프로스 | 통신용 ｒｆ 필터에 적용된 마그네슘 합금용 구리표면 부식방지제 조성물 및 처리방법 |
| ES2905443T3 (es) | 2015-05-28 | 2022-04-08 | Ecolab Usa Inc | Inhibidores de la corrosión a base de purina |
| MX2017015289A (es) | 2015-05-28 | 2018-02-19 | Ecolab Usa Inc | Inhibidores de corrosion de imidazol y bencimidazol 2-sustituidos. |
| CN109487257A (zh) * | 2018-11-13 | 2019-03-19 | 南通赛可特电子有限公司 | 一种osp铜面抗氧化剂及其制备方法 |
| WO2021194688A1 (en) | 2020-03-27 | 2021-09-30 | Ecolab Usa Inc. | Galvanized metal corrosion inhibitor compositions and methods of use |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1067026B (de) * | 1958-01-29 | 1959-10-15 | Farbenfabriken Bayer Aktiengesellschaft, Leverkusen-Bayerwerk | Verfahren zur Herstellung blutdrucksteigernder Ben zimidazoldenvate |
| NL135043C (en, 2012) * | 1963-10-11 | |||
| CH580678A5 (en, 2012) * | 1972-12-04 | 1976-10-15 | Ciba Geigy Ag | |
| US4074046A (en) * | 1974-01-21 | 1978-02-14 | American Cyanamid Company | Process for azoles (ring closure of nitro compounds) |
| DE3540376A1 (de) * | 1985-11-14 | 1987-05-21 | Bayer Ag | Verfahren zur inhibierung der wasserstoffinduzierten korrosion von metallischen werkstoffen |
| JP2526265B2 (ja) * | 1988-02-19 | 1996-08-21 | 富士通株式会社 | 多重試験方式 |
| JP2667257B2 (ja) * | 1989-08-17 | 1997-10-27 | 東レ株式会社 | ポリアミド樹脂組成物 |
| JPH03124395A (ja) * | 1989-10-03 | 1991-05-27 | Hideyuki Kawai | はんだ付け用プレフラックス |
| KR960008153B1 (ko) * | 1989-10-03 | 1996-06-20 | 다찌바나 다이끼찌 | 금속 공작용 표면 처리제 |
| US5478607A (en) * | 1991-05-17 | 1995-12-26 | Hitachi Telecon Technologies Ltd. | Method for use of preflux, printed wiring board, and method for production thereof |
-
1992
- 1992-11-25 TW TW081109451A patent/TW217426B/zh active
- 1992-12-24 KR KR1019920025495A patent/KR100263516B1/ko not_active Expired - Fee Related
-
1993
- 1993-01-06 JP JP5015873A patent/JPH05263275A/ja active Pending
- 1993-01-07 DE DE69302021T patent/DE69302021T2/de not_active Expired - Lifetime
- 1993-01-07 SG SG1996004399A patent/SG52429A1/en unknown
- 1993-01-07 EP EP93100160A patent/EP0551112B1/en not_active Expired - Lifetime
-
1994
- 1994-02-14 US US08/195,015 patent/US5435860A/en not_active Expired - Fee Related
- 1994-05-26 US US08/250,350 patent/US5476947A/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07142846A (ja) * | 1993-11-17 | 1995-06-02 | Nec Corp | 印刷配線板の製造方法 |
| JPH08148811A (ja) * | 1994-11-22 | 1996-06-07 | Nec Toyama Ltd | プリント配線板の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| SG52429A1 (en) | 1998-09-28 |
| EP0551112B1 (en) | 1996-04-03 |
| US5435860A (en) | 1995-07-25 |
| TW217426B (en, 2012) | 1993-12-11 |
| KR100263516B1 (ko) | 2000-08-01 |
| US5476947A (en) | 1995-12-19 |
| DE69302021T2 (de) | 1996-09-19 |
| KR930016403A (ko) | 1993-08-26 |
| EP0551112A1 (en) | 1993-07-14 |
| DE69302021D1 (de) | 1996-05-09 |
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