EP0343559B2 - Utilisation de composés éthane sulfone substitués en position 2 comme agents auxiliaires galvaniques - Google Patents
Utilisation de composés éthane sulfone substitués en position 2 comme agents auxiliaires galvaniques Download PDFInfo
- Publication number
- EP0343559B2 EP0343559B2 EP89109164A EP89109164A EP0343559B2 EP 0343559 B2 EP0343559 B2 EP 0343559B2 EP 89109164 A EP89109164 A EP 89109164A EP 89109164 A EP89109164 A EP 89109164A EP 0343559 B2 EP0343559 B2 EP 0343559B2
- Authority
- EP
- European Patent Office
- Prior art keywords
- compounds
- galvanic
- auxiliary agents
- substituted ethane
- pyridinium
- 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
- -1 2-substituted ethane sulfone compounds Chemical class 0.000 title description 3
- 239000012752 auxiliary agent Substances 0.000 title 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 6
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- 238000009713 electroplating Methods 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 3
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 229960003237 betaine Drugs 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- BMPBPPRKJPBLKR-UHFFFAOYSA-N CC(C[N+]1=CC=CC=C1)S([O-])(=O)=O Chemical compound CC(C[N+]1=CC=CC=C1)S([O-])(=O)=O BMPBPPRKJPBLKR-UHFFFAOYSA-N 0.000 description 1
- HIIAZTSDAJUCDC-UHFFFAOYSA-N CCCC(C[N+]1=CC=CC=C1)S([O-])(=O)=O Chemical compound CCCC(C[N+]1=CC=CC=C1)S([O-])(=O)=O HIIAZTSDAJUCDC-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000013527 degreasing agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- PVYOEOXGRHEUNY-UHFFFAOYSA-M sodium;2-sulfanylpropane-1-sulfonate Chemical compound [Na+].CC(S)CS([O-])(=O)=O PVYOEOXGRHEUNY-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- GINSRDSEEGBTJO-UHFFFAOYSA-N thietane 1-oxide Chemical class O=S1CCC1 GINSRDSEEGBTJO-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
- C25D3/12—Electroplating: Baths therefor from solutions of nickel or cobalt
-
- 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
-
- 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
Definitions
- propanesulfone compounds with a pyridinium substituent or a quinoline substituent in the 3-position are known for electroplating purposes as brighteners and levelers in acidic nickel baths (cf. DE-PS 1 004 011).
- 2-substituted ethanesulfone compounds used according to the invention with an alkyl chain branching at the C2 show good gloss formation and leveling, in particular of nickel and copper coatings, although the steric hindrance leads to poor results. In this way, numerous substance variants allow adaptation and optimization to different galvanic requirements.
- the pyridine and quinoline derivatives of the 2-substituted ethanesulfone betaines in particular are particularly good brighteners and levelers in acidic nickel baths, while the mercapto derivatives are suitable as brighteners in acidic copper baths.
- a galvanic nickel bath was set up as follows: 50 g / l Boric acid 70 g / l Nickel chloride .6 H 2 O 330 g / l Nickel sulfate .7 H 2 O 2 g / l Saccharin 0.2 g / l Trial connection 0.02 g / l Leveler (epichlorohydrin-propargyl alcohol adduct) distilled water to 1 liter, pH 4.0 adjusted with sulfuric acid.
- the sheets After the nickel plating, the sheets showed a uniform surface, good gloss and leveling.
- the storage stability of the prepared additional solution at 60 ° C was good.
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Claims (3)
- Utilisation de composés éthanesulfonés substitués en position 2 de formule générale I
[A-CHR3-CH2-SO3 ]- (I)
et de leurs sels alcaline ou d'ammonium, dans laquelle R3 représente un alkyle inférieur en C1 - C4 et A représente(1) un reste pyridinium dont les substituants R1 et R2 représentent un hydrogène ou alkyle inférieur en C1 - C3, ou les substituants R1 et R2 représentent ensemble avec la reste pyridinium, un cycle aromatique condensé à 6 chaînons, ou(2) un SH-groupecomme substance auxiliaire dans les techniques galvaniques. - Utilisation de composés de formule I avec A = (1) comme agent de brillance et agent égalisateur dans les bains galvaniques acides au nickel.
- Utilisation de composés de fromule I avec A = (2) comme agent de brillance dans les bains galvaniques acides au cuivre.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3817722A DE3817722A1 (de) | 1988-05-25 | 1988-05-25 | Verwendung von 2-substituierten ethansulfon-verbindungen als galvanotechnische hilfsstoffe |
| DE3817722 | 1988-05-25 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0343559A1 EP0343559A1 (fr) | 1989-11-29 |
| EP0343559B1 EP0343559B1 (fr) | 1993-03-31 |
| EP0343559B2 true EP0343559B2 (fr) | 1996-07-10 |
Family
ID=6355072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP89109164A Expired - Lifetime EP0343559B2 (fr) | 1988-05-25 | 1989-05-22 | Utilisation de composés éthane sulfone substitués en position 2 comme agents auxiliaires galvaniques |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US5024736A (fr) |
| EP (1) | EP0343559B2 (fr) |
| JP (1) | JP2505281B2 (fr) |
| DE (2) | DE3817722A1 (fr) |
| ES (1) | ES2053865T5 (fr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2242200B (en) * | 1990-02-20 | 1993-11-17 | Omi International | Plating compositions and processes |
| DE4013349A1 (de) * | 1990-04-23 | 1991-10-24 | Schering Ag | 1-(2-sulfoaethyl)pyridiniumbetain, verfahren zu dessen herstellung sowie saure nickelbaeder enthaltend diese verbindung |
| US5523861A (en) | 1991-05-15 | 1996-06-04 | Canon Kabushiki Kaisha | Image reader capable of setting density and illumination |
| US6605204B1 (en) * | 1999-10-14 | 2003-08-12 | Atofina Chemicals, Inc. | Electroplating of copper from alkanesulfonate electrolytes |
| US6776893B1 (en) * | 2000-11-20 | 2004-08-17 | Enthone Inc. | Electroplating chemistry for the CU filling of submicron features of VLSI/ULSI interconnect |
| EP2801640A1 (fr) * | 2013-05-08 | 2014-11-12 | ATOTECH Deutschland GmbH | Bain électrolytique de nickel galvanique ou d'alliage de nickel pour déposer un alliage de nickel ou de nickel mi-lustré |
| DE102014207778B3 (de) * | 2014-04-25 | 2015-05-21 | Kiesow Dr. Brinkmann GmbH & Co. KG | Verwendung einer Mischung zur Verwendung in einem galvanischen Bad oder eines galvanischen Bades zur Herstellung einer Glanznickelschicht sowie Verfahren zur Herstellung eines Artikels mit einer Glanznickelschicht |
| MX2021005299A (es) | 2018-11-07 | 2021-09-14 | Coventya Inc | Ba?o de cobre satinado y metodo de deposito de una capa de cobre satinado. |
| WO2020212346A1 (fr) * | 2019-04-15 | 2020-10-22 | Atotech Deutschland Gmbh | Bain d'électrodéposition galvanique de nickel ou d'alliage de nickel pour le dépôt d'un revêtement semi-brillant de nickel ou d'alliage de nickel semi-brillant |
| DE102020212830B4 (de) | 2020-10-12 | 2022-08-18 | Sms Group Gmbh | Einstellsystem zum Einstellen des Führungsspiels einer Gleitführung für bewegbare Teile einer Presse sowie Verfahren zum Einstellen der Position wenigstens eines Gleitblocks einer Gleitführung an einer Presse |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1075398B (de) * | 1954-03-22 | 1960-02-11 | DEHYDAG Deutsche Hydrierwerke G.m.b.H., Düsseldorf | Bad zur galvanischen Herstellung von Metallüberzügen |
| NL205377A (fr) * | 1955-03-16 | |||
| DE1092744B (de) * | 1958-12-17 | 1960-11-10 | Dehydag Gmbh | Saures galvanisches Nickelbad |
| DE1238032B (de) * | 1962-07-21 | 1967-04-06 | Dehydag Gmbh | Verfahren zur Herstellung von Oxygruppen enthaltenden Sulfobetainen |
| DE1205973B (de) * | 1963-02-02 | 1965-12-02 | Dehydag Gmbh | Verfahren zur Herstellung von Oxygruppen enthaltenden Thiosulfobetainen |
| DE1191652B (de) * | 1963-05-15 | 1965-04-22 | Dehydag Gmbh | Saures galvanisches Nickelbad |
| US3328273A (en) * | 1966-08-15 | 1967-06-27 | Udylite Corp | Electro-deposition of copper from acidic baths |
| DE2803493A1 (de) * | 1978-01-27 | 1979-08-02 | Agfa Gevaert Ag | Verfahren zur herstellung von sulfoalkylquartaersalzen |
| FI70304C (fi) * | 1980-02-27 | 1986-09-15 | Kee Klamps Ltd | Roeranslutning |
| US4526968A (en) * | 1981-08-24 | 1985-07-02 | M&T Chemicals Inc. | Quaternary aminehydroxypropane sulfobetaines |
| US4555315A (en) * | 1984-05-29 | 1985-11-26 | Omi International Corporation | High speed copper electroplating process and bath therefor |
| DE3541098A1 (de) * | 1985-11-21 | 1987-05-27 | Agfa Gevaert Ag | Sulfoalkylierungsverfahren |
-
1988
- 1988-05-25 DE DE3817722A patent/DE3817722A1/de not_active Withdrawn
-
1989
- 1989-05-22 EP EP89109164A patent/EP0343559B2/fr not_active Expired - Lifetime
- 1989-05-22 DE DE8989109164T patent/DE58903912D1/de not_active Expired - Fee Related
- 1989-05-22 ES ES89109164T patent/ES2053865T5/es not_active Expired - Lifetime
- 1989-05-24 JP JP1129048A patent/JP2505281B2/ja not_active Expired - Fee Related
- 1989-05-24 US US07/357,044 patent/US5024736A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0273990A (ja) | 1990-03-13 |
| JP2505281B2 (ja) | 1996-06-05 |
| DE3817722A1 (de) | 1989-12-14 |
| EP0343559B1 (fr) | 1993-03-31 |
| DE58903912D1 (de) | 1993-05-06 |
| ES2053865T3 (es) | 1994-08-01 |
| US5024736A (en) | 1991-06-18 |
| EP0343559A1 (fr) | 1989-11-29 |
| ES2053865T5 (es) | 1996-11-16 |
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