CA2093924C - Acid bath for copper plating - Google Patents
Acid bath for copper plating Download PDFInfo
- Publication number
- CA2093924C CA2093924C CA002093924A CA2093924A CA2093924C CA 2093924 C CA2093924 C CA 2093924C CA 002093924 A CA002093924 A CA 002093924A CA 2093924 A CA2093924 A CA 2093924A CA 2093924 C CA2093924 C CA 2093924C
- Authority
- CA
- Canada
- Prior art keywords
- bath
- beta
- bath according
- phenazonium
- naphthol
- 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.)
- Expired - Lifetime
Links
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 229910052802 copper Inorganic materials 0.000 title claims abstract description 27
- 239000010949 copper Substances 0.000 title claims abstract description 27
- 239000002253 acid Substances 0.000 title claims description 9
- 238000007747 plating Methods 0.000 title description 3
- 239000011260 aqueous acid Substances 0.000 claims abstract description 8
- 230000008021 deposition Effects 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 28
- -1 nitrogen-containing thio compound Chemical class 0.000 claims description 18
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 17
- 238000000576 coating method Methods 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 239000003792 electrolyte Substances 0.000 claims description 13
- 229920000642 polymer Polymers 0.000 claims description 13
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 159000000000 sodium salts Chemical class 0.000 claims description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
- 229910000365 copper sulfate Inorganic materials 0.000 claims description 7
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 7
- 239000002202 Polyethylene glycol Substances 0.000 claims description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- 150000003585 thioureas Chemical class 0.000 claims description 4
- CQNZIRSBRGJNTO-UHFFFAOYSA-N 1,3-thiazolidine-2-thiol Chemical compound SC1NCCS1 CQNZIRSBRGJNTO-UHFFFAOYSA-N 0.000 claims description 3
- OBDVFOBWBHMJDG-UHFFFAOYSA-N 3-mercapto-1-propanesulfonic acid Chemical compound OS(=O)(=O)CCCS OBDVFOBWBHMJDG-UHFFFAOYSA-N 0.000 claims description 3
- PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 claims description 3
- IPCRBOOJBPETMF-UHFFFAOYSA-N N-acetylthiourea Chemical compound CC(=O)NC(N)=S IPCRBOOJBPETMF-UHFFFAOYSA-N 0.000 claims description 3
- HTKFORQRBXIQHD-UHFFFAOYSA-N allylthiourea Chemical compound NC(=S)NCC=C HTKFORQRBXIQHD-UHFFFAOYSA-N 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- RXRJFXGYBHBKBJ-UHFFFAOYSA-N 1-sulfanylimidazolidine Chemical compound SN1CCNC1 RXRJFXGYBHBKBJ-UHFFFAOYSA-N 0.000 claims 8
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims 8
- 229920001522 polyglycol ester Polymers 0.000 claims 8
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 4
- 229920001451 polypropylene glycol Polymers 0.000 claims 4
- VQRWKFKETIQVSP-UHFFFAOYSA-N 2,3-dihydro-1,3-thiazole-2-thiol Chemical compound SC1NC=CS1 VQRWKFKETIQVSP-UHFFFAOYSA-N 0.000 claims 2
- BVPHXTUEZOQIBS-UHFFFAOYSA-N 6-methyl-1h-pyrimidine-2-thione Chemical compound CC1=CC=NC(S)=N1 BVPHXTUEZOQIBS-UHFFFAOYSA-N 0.000 claims 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims 2
- GMEHFXXZSWDEDB-UHFFFAOYSA-N N-ethylthiourea Chemical compound CCNC(N)=S GMEHFXXZSWDEDB-UHFFFAOYSA-N 0.000 claims 2
- 239000004372 Polyvinyl alcohol Substances 0.000 claims 2
- 239000001768 carboxy methyl cellulose Substances 0.000 claims 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims 2
- IUOYQVWAOBUMLY-UHFFFAOYSA-N n-carbamothioyl-2,2,2-trifluoroacetamide Chemical compound NC(=S)NC(=O)C(F)(F)F IUOYQVWAOBUMLY-UHFFFAOYSA-N 0.000 claims 2
- NLEQMBHQFHUCST-UHFFFAOYSA-N n-carbamothioyl-2-cyanoacetamide Chemical compound NC(=S)NC(=O)CC#N NLEQMBHQFHUCST-UHFFFAOYSA-N 0.000 claims 2
- ACLZYRNSDLQOIA-UHFFFAOYSA-N o-tolylthiourea Chemical compound CC1=CC=CC=C1NC(N)=S ACLZYRNSDLQOIA-UHFFFAOYSA-N 0.000 claims 2
- 229920001521 polyalkylene glycol ether Polymers 0.000 claims 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 2
- 229960004063 propylene glycol Drugs 0.000 claims 2
- ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical compound O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 claims 2
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 claims 2
- 238000009713 electroplating Methods 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 5
- 238000009499 grossing Methods 0.000 description 4
- APWIQNJBGHKQRN-UHFFFAOYSA-N imidazolidine-2-thiol Chemical compound SC1NCCN1 APWIQNJBGHKQRN-UHFFFAOYSA-N 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 3
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 1
- MWXMWLZIZRDIBL-UHFFFAOYSA-N 5-phenyl-4a,10-dihydro-4h-phenazin-10-ium-2-amine;chloride Chemical compound [Cl-].C12=CC=CC=C2[NH2+]C2=CC(N)=CCC2N1C1=CC=CC=C1 MWXMWLZIZRDIBL-UHFFFAOYSA-N 0.000 description 1
- KYOGPZIVCWSXTO-UHFFFAOYSA-N 6-methyl-1h-pyrimidine-2-thione;2-sulfanylidene-1h-pyrimidin-4-one Chemical compound CC1=CC=NC(=S)N1.O=C1C=CNC(=S)N1 KYOGPZIVCWSXTO-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 235000021539 instant coffee Nutrition 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- MQWKHMLZCMWUMX-UHFFFAOYSA-N n-carbamothioyl-2-cyanoacetamide;ethylthiourea Chemical compound CCNC(N)=S.NC(=S)NC(=O)CC#N MQWKHMLZCMWUMX-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 150000003580 thiophosphoric acid esters Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25D—PROCESSES FOR THE ELECTROLYTIC OR ELECTROPHORETIC PRODUCTION OF COATINGS; ELECTROFORMING; APPARATUS THEREFOR
- C25D3/00—Electroplating: Baths therefor
- C25D3/02—Electroplating: Baths therefor from solutions
- C25D3/38—Electroplating: Baths therefor from solutions of copper
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Organic Chemistry (AREA)
- Electroplating And Plating Baths Therefor (AREA)
- Electrolytic Production Of Metals (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4032864A DE4032864A1 (de) | 1990-10-13 | 1990-10-13 | Saures bad zur galvanischen abscheidung von kupferueberzuegen und verfahren unter verwendung dieser kombination |
DEP4032864.3 | 1990-10-13 | ||
PCT/DE1991/000811 WO1992007116A1 (de) | 1990-10-13 | 1991-10-11 | Saures bad zur galvanischen abscheidung von kupferüberzügen und verfahren unter verwendung dieser kombination |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2093924A1 CA2093924A1 (en) | 1992-04-14 |
CA2093924C true CA2093924C (en) | 2002-02-05 |
Family
ID=6416407
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002093924A Expired - Lifetime CA2093924C (en) | 1990-10-13 | 1991-10-11 | Acid bath for copper plating |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP0554275B1 (enrdf_load_stackoverflow) |
JP (1) | JPH06501986A (enrdf_load_stackoverflow) |
AT (1) | ATE115651T1 (enrdf_load_stackoverflow) |
CA (1) | CA2093924C (enrdf_load_stackoverflow) |
DE (2) | DE4032864A1 (enrdf_load_stackoverflow) |
ES (1) | ES2066477T3 (enrdf_load_stackoverflow) |
WO (1) | WO1992007116A1 (enrdf_load_stackoverflow) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10261852B3 (de) * | 2002-12-20 | 2004-06-03 | Atotech Deutschland Gmbh | Gemisch oligomerer Phenaziniumverbindungen und dessen Herstellungsverfahren, saures Bad zur elektrolytischen Abscheidung eines Kupferniederschlages, enthaltend die oligomeren Phenaziniumverbindungen, sowie Verfahren zum elektrolytischen Abscheiden eines Kupferniederschlages mit einem das Gemisch enthaltenden Bad |
DE10337669B4 (de) * | 2003-08-08 | 2006-04-27 | Atotech Deutschland Gmbh | Wässrige, saure Lösung und Verfahren zum galvanischen Abscheiden von Kupferüberzügen sowie Verwendung der Lösung |
DE102004041701A1 (de) * | 2004-08-28 | 2006-03-02 | Enthone Inc., West Haven | Verfahren zur elektrolytischen Abscheidung von Metallen |
US7282602B2 (en) * | 2004-09-21 | 2007-10-16 | Bionumerik Pharmaceuticals, Inc. | Medicinal disulfide salts |
KR101362062B1 (ko) * | 2006-01-27 | 2014-02-11 | 오꾸노 케미칼 인더스트리즈 컴파니,리미티드 | 함인동을 애노드로 하는 전해 동도금액용 첨가제, 전해동도금액 및 전해 동도금 방법 |
DE102014208733A1 (de) | 2014-05-09 | 2015-11-12 | Dr. Hesse Gmbh & Cie Kg | Verfahren zum elektrolytischen Abscheiden von Kupfer aus Wasser basierenden Elektrolyten |
EP3497267B1 (en) | 2016-08-15 | 2020-04-29 | ATOTECH Deutschland GmbH | Acidic aqueous composition for electrolytic copper plating |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL291575A (enrdf_load_stackoverflow) * | 1962-04-16 | |||
DE1246347B (de) * | 1966-03-08 | 1967-08-03 | Schering Ag | Saures galvanisches Kupferbad |
DE2028803C3 (de) * | 1970-06-06 | 1980-08-14 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Polymere Phenazoniumverbindungen |
GB1526076A (en) * | 1975-03-11 | 1978-09-27 | Oxy Metal Industries Corp | Electrodeposition of copper |
DE2721985A1 (de) * | 1977-05-14 | 1978-11-16 | Bayer Ag | Verfahren zur herstellung von urethan- und/oder harnstoffgruppen aufweisenden polyisocyanat polyadditionsprodukten |
DE2746938C2 (de) * | 1977-10-17 | 1987-04-09 | Schering AG, 1000 Berlin und 4709 Bergkamen | Wäßriges saures Bad zur galvanischen Abscheidung von glänzenden und rißfreien Kupferüberzügen und Verwendung dieses Bades |
US4272335A (en) * | 1980-02-19 | 1981-06-09 | Oxy Metal Industries Corporation | Composition and method for electrodeposition of copper |
US4374709A (en) * | 1980-05-01 | 1983-02-22 | Occidental Chemical Corporation | Process for plating polymeric substrates |
US4376685A (en) * | 1981-06-24 | 1983-03-15 | M&T Chemicals Inc. | Acid copper electroplating baths containing brightening and leveling additives |
FR2510145B1 (fr) * | 1981-07-24 | 1986-02-07 | Rhone Poulenc Spec Chim | Additif pour bain de cuivrage electrolytique acide, son procede de preparation et son application au cuivrage des circuits imprimes |
JPS59501829A (ja) * | 1982-09-30 | 1984-11-01 | リ−ロ−ナル インコ−ポレ−テツド | 電気銅メッキ液 |
DE3402999A1 (de) * | 1984-01-28 | 1985-08-01 | Skw Trostberg Ag, 8223 Trostberg | Duengerloesungen |
DE3721985A1 (de) * | 1987-06-30 | 1989-01-12 | Schering Ag | Waessriges saures bad zur galvanischen abscheidung glaenzender und eingeebneter kupferueberzuege |
-
1990
- 1990-10-13 DE DE4032864A patent/DE4032864A1/de active Granted
-
1991
- 1991-10-11 DE DE59103933T patent/DE59103933D1/de not_active Expired - Lifetime
- 1991-10-11 CA CA002093924A patent/CA2093924C/en not_active Expired - Lifetime
- 1991-10-11 ES ES91917496T patent/ES2066477T3/es not_active Expired - Lifetime
- 1991-10-11 AT AT91917496T patent/ATE115651T1/de not_active IP Right Cessation
- 1991-10-11 JP JP3516095A patent/JPH06501986A/ja active Pending
- 1991-10-11 WO PCT/DE1991/000811 patent/WO1992007116A1/de active IP Right Grant
- 1991-10-11 EP EP91917496A patent/EP0554275B1/de not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
DE4032864C2 (enrdf_load_stackoverflow) | 1993-01-07 |
DE59103933D1 (de) | 1995-01-26 |
ES2066477T3 (es) | 1995-03-01 |
EP0554275A1 (de) | 1993-08-11 |
DE4032864A1 (de) | 1992-04-16 |
CA2093924A1 (en) | 1992-04-14 |
JPH06501986A (ja) | 1994-03-03 |
ATE115651T1 (de) | 1994-12-15 |
EP0554275B1 (de) | 1994-12-14 |
WO1992007116A1 (de) | 1992-04-30 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKLA | Lapsed | ||
MKEC | Expiry (correction) |
Effective date: 20121202 |