EP0069331B1 - Utilisation des sels d'acides vinylsulfoniques stabilisés avec des hydroxylamines N-nitroso-N-alkyle ou cycloalkyle comme brillanteurs primaires dans des bains galvaniques de nickel - Google Patents
Utilisation des sels d'acides vinylsulfoniques stabilisés avec des hydroxylamines N-nitroso-N-alkyle ou cycloalkyle comme brillanteurs primaires dans des bains galvaniques de nickel Download PDFInfo
- Publication number
- EP0069331B1 EP0069331B1 EP82105806A EP82105806A EP0069331B1 EP 0069331 B1 EP0069331 B1 EP 0069331B1 EP 82105806 A EP82105806 A EP 82105806A EP 82105806 A EP82105806 A EP 82105806A EP 0069331 B1 EP0069331 B1 EP 0069331B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- nitroso
- salts
- alkyl
- vinyl
- vinyl sulfonate
- 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
Links
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 title claims description 16
- -1 cycloalkyl hydroxyl amines Chemical class 0.000 title claims description 13
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical class OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 title claims description 13
- 229910052759 nickel Inorganic materials 0.000 title claims description 8
- 150000003839 salts Chemical class 0.000 title description 5
- 239000003381 stabilizer Substances 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000009713 electroplating Methods 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- NLVXSWCKKBEXTG-UHFFFAOYSA-M ethenesulfonate Chemical compound [O-]S(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-M 0.000 description 12
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000003792 electrolyte Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 229910001369 Brass Inorganic materials 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 239000010951 brass Substances 0.000 description 2
- 238000005282 brightening Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000005868 electrolysis reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- PSBDWGZCVUAZQS-UHFFFAOYSA-N (dimethylsulfonio)acetate Chemical compound C[S+](C)CC([O-])=O PSBDWGZCVUAZQS-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- PHRZTXWNFAEVIA-UHFFFAOYSA-N hydroxylamine;potassium Chemical compound [K].ON PHRZTXWNFAEVIA-UHFFFAOYSA-N 0.000 description 1
- NFMHSPWHNQRFNR-UHFFFAOYSA-N hyponitrous acid Chemical class ON=NO NFMHSPWHNQRFNR-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- VXVTWBRLTJLQBZ-UHFFFAOYSA-N n-cyclohexyl-n-hydroxynitrous amide;potassium Chemical compound [K].O=NN(O)C1CCCCC1 VXVTWBRLTJLQBZ-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000009467 reduction 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
- 229910052708 sodium Inorganic materials 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229940117986 sulfobetaine Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
- C25D3/12—Electroplating: Baths therefor from solutions of nickel or cobalt
Definitions
- N-nitroso-N-alkyl- or -cycloalkylhydroxylamine salts which are known per se from DE-PS 1 092 005 as stabilizers of ethylenically unsaturated compounds.
- vinyl sulfonates are not mentioned as suitable compounds to be stabilized, and the person skilled in the art also had to consider the use of nitroso compounds in galvanic baths to be quite questionable, since it could be assumed that these substances could have an adverse effect on the electrolysis process.
- R herein represents a C 4 - to C lo alkyl, preferably n-pentyl, n-hexyl, 2-ethylhexyl, n-octyl or 3,5,5-trimethylpentyl ( "Isononyl") residue.
- R further represents a C 5 - to C 10 cycloalkyl radical, e.g. B. the cyclopentyl, cyclohexyl, cyclooctyl or decahydronaphthyl, which may optionally be substituted by halogen or cyano groups.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Claims (3)
1. Utilisation de sulfonates vinyliques de métal alcalin comme brillanteurs de fond dans les bains de nickelage électrolytique, caractérisée par le fait que les sulfonates à utiliser contiennent, ajoutés en mélange, comme stabilisants, des composés de formule
dans laquelle R représente un reste aliphatique en C4 à C10 ou cycloaliphatique en C5 à C10 et Me un métal alcalin ou un reste ammonium.
2. Utilisation de sulfonates vinyliques selon la revendication 1, caractérisée par le fait que les sulfonates vinyliques contiennent, ajoutés en mélange, comme stabilisants, des sels de métal alcalin de N-nitroso-N-cycloalkylhydroxylamine.
3. Utilisation de sulfonates vinyliques selon la revendication 1 ou 2, caractérisée par le fait que les stabilisants sont ajoutés en mélange à raison de 0,005 à 1 % en poids, rapportés à l'acide vinylsulfonique déshydraté.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3126836 | 1981-07-08 | ||
| DE19813126836 DE3126836A1 (de) | 1981-07-08 | 1981-07-08 | Verwendung von mit n-nitroso-n-alkyl- oder cycloalkylhydroxylaminen stabilisierten salzen der vinylsulfonsaeure als grundglanzbildner in galvanischen nickelbaedern |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0069331A2 EP0069331A2 (fr) | 1983-01-12 |
| EP0069331A3 EP0069331A3 (en) | 1986-02-05 |
| EP0069331B1 true EP0069331B1 (fr) | 1987-08-19 |
Family
ID=6136342
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP82105806A Expired EP0069331B1 (fr) | 1981-07-08 | 1982-06-30 | Utilisation des sels d'acides vinylsulfoniques stabilisés avec des hydroxylamines N-nitroso-N-alkyle ou cycloalkyle comme brillanteurs primaires dans des bains galvaniques de nickel |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP0069331B1 (fr) |
| DE (2) | DE3126836A1 (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1308541A1 (fr) * | 2001-10-04 | 2003-05-07 | Shipley Company LLC | Bain et procédé pour le dépôt d'une couche metallique sur un substrat |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1092005B (de) * | 1958-03-27 | 1960-11-03 | Basf Ag | Stabilisierung von aethylenisch ungesaettigten, polymerisierbaren, monomeren Verbindungen gegen Polymerisation |
| DE2054221B2 (de) * | 1970-11-04 | 1973-11-08 | Badische Anilin- & Soda-Fabrik Ag, 6700 Ludwigshafen | Stabilisierte wässrige Losungen ungesättigter aliphaüscher Sulfon sauren bzw ihrer Salze |
-
1981
- 1981-07-08 DE DE19813126836 patent/DE3126836A1/de not_active Withdrawn
-
1982
- 1982-06-30 DE DE8282105806T patent/DE3277023D1/de not_active Expired
- 1982-06-30 EP EP82105806A patent/EP0069331B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3126836A1 (de) | 1983-01-27 |
| EP0069331A3 (en) | 1986-02-05 |
| DE3277023D1 (en) | 1987-09-24 |
| EP0069331A2 (fr) | 1983-01-12 |
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| Date | Code | Title | Description |
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| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
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