CA2254106C - Composition and method for reducing copper oxide to metallic copper - Google Patents
Composition and method for reducing copper oxide to metallic copper Download PDFInfo
- Publication number
- CA2254106C CA2254106C CA002254106A CA2254106A CA2254106C CA 2254106 C CA2254106 C CA 2254106C CA 002254106 A CA002254106 A CA 002254106A CA 2254106 A CA2254106 A CA 2254106A CA 2254106 C CA2254106 C CA 2254106C
- Authority
- CA
- Canada
- Prior art keywords
- reducing
- copper
- copper oxide
- concentration
- ppm
- 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 - Fee Related
Links
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 title claims abstract description 92
- 239000005751 Copper oxide Substances 0.000 title claims abstract description 78
- 229910000431 copper oxide Inorganic materials 0.000 title claims abstract description 78
- 239000010949 copper Substances 0.000 title claims abstract description 75
- 229910052802 copper Inorganic materials 0.000 title claims abstract description 75
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims abstract description 74
- 239000000203 mixture Substances 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims description 29
- YJROYUJAFGZMJA-UHFFFAOYSA-N boron;morpholine Chemical compound [B].C1COCCN1 YJROYUJAFGZMJA-UHFFFAOYSA-N 0.000 claims abstract description 70
- 229920005989 resin Polymers 0.000 claims abstract description 27
- 239000011347 resin Substances 0.000 claims abstract description 27
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea group Chemical group NC(=S)N UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 102
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 51
- 239000002253 acid Substances 0.000 claims description 44
- 230000009467 reduction Effects 0.000 claims description 33
- 238000011946 reduction process Methods 0.000 claims description 30
- 239000003381 stabilizer Substances 0.000 claims description 30
- 239000003638 chemical reducing agent Substances 0.000 claims description 22
- 230000004580 weight loss Effects 0.000 claims description 22
- 230000006872 improvement Effects 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims 1
- 229960004643 cupric oxide Drugs 0.000 description 67
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
- 239000000243 solution Substances 0.000 description 56
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 42
- 229910000085 borane Inorganic materials 0.000 description 36
- 238000006722 reduction reaction Methods 0.000 description 34
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 26
- -1 amine boranes Chemical class 0.000 description 20
- 230000000977 initiatory effect Effects 0.000 description 15
- 229940113083 morpholine Drugs 0.000 description 13
- 230000007306 turnover Effects 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- RJTANRZEWTUVMA-UHFFFAOYSA-N boron;n-methylmethanamine Chemical compound [B].CNC RJTANRZEWTUVMA-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000012360 testing method Methods 0.000 description 5
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- VJNDZIJEKQZBPZ-UHFFFAOYSA-N morpholine;thiourea Chemical compound NC(N)=S.C1COCCN1 VJNDZIJEKQZBPZ-UHFFFAOYSA-N 0.000 description 3
- CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2h-benzotriazole Chemical compound CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 description 2
- FKPXGNGUVSHWQQ-UHFFFAOYSA-N 5-methyl-1,2-oxazol-3-amine Chemical compound CC1=CC(N)=NO1 FKPXGNGUVSHWQQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000004697 Polyetherimide Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004734 Polyphenylene sulfide Substances 0.000 description 2
- JBANFLSTOJPTFW-UHFFFAOYSA-N azane;boron Chemical compound [B].N JBANFLSTOJPTFW-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 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 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 230000003278 mimic effect Effects 0.000 description 2
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
- 229920006122 polyamide resin Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920001601 polyetherimide Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000069 polyphenylene sulfide Polymers 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- MBFWOEIDDNBKHS-UHFFFAOYSA-N B.N1CCOCC1.N1CCOCC1 Chemical compound B.N1CCOCC1.N1CCOCC1 MBFWOEIDDNBKHS-UHFFFAOYSA-N 0.000 description 1
- 101100148780 Caenorhabditis elegans sec-16A.1 gene Proteins 0.000 description 1
- 206010013496 Disturbance in attention Diseases 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 1
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 1
- 229940112669 cuprous oxide Drugs 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229940061319 ovide Drugs 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 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
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B6/00—Hydrides of metals including fully or partially hydrided metals, alloys or intermetallic compounds ; Compounds containing at least one metal-hydrogen bond, e.g. (GeH3)2S, SiH GeH; Monoborane or diborane; Addition complexes thereof
- C01B6/06—Hydrides of aluminium, gallium, indium, thallium, germanium, tin, lead, arsenic, antimony, bismuth or polonium; Monoborane; Diborane; Addition complexes thereof
- C01B6/10—Monoborane; Diborane; Addition complexes thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
- C09J5/04—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving separate application of adhesive ingredients to the different surfaces to be joined
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Manufacturing Of Printed Wiring (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Chemically Coating (AREA)
- Chemical Treatment Of Metals (AREA)
- Manufacture And Refinement Of Metals (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1997/013423 WO1999002452A1 (en) | 1995-12-19 | 1997-07-10 | Composition and method for reducing copper oxide to metallic copper |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2254106A1 CA2254106A1 (en) | 1999-01-10 |
| CA2254106C true CA2254106C (en) | 2003-12-16 |
Family
ID=22261368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002254106A Expired - Fee Related CA2254106C (en) | 1997-07-10 | 1997-07-10 | Composition and method for reducing copper oxide to metallic copper |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0938447B1 (https=) |
| JP (1) | JP3431170B2 (https=) |
| KR (1) | KR100375589B1 (https=) |
| AT (1) | ATE256085T1 (https=) |
| CA (1) | CA2254106C (https=) |
| DE (1) | DE69726752T2 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3718722B2 (ja) * | 1998-02-20 | 2005-11-24 | モートン インターナショナル，インコーポレイティド | 銅酸化物を金属銅に還元するための組成物および方法 |
| JP3387893B2 (ja) | 2000-05-26 | 2003-03-17 | マクダーミッド インコーポレーテッド | 金属表面へのポリマー材料の接着性改良方法 |
| JP6926120B2 (ja) * | 2016-05-04 | 2021-08-25 | アトテツク・ドイチユラント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツングＡｔｏｔｅｃｈ Ｄｅｕｔｓｃｈｌａｎｄ ＧｍｂＨ | 基板表面の活性化を含む基板表面に金属または金属合金を析出させるための方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4255194A (en) * | 1979-01-15 | 1981-03-10 | Mine Safety Appliances Company | Palladium alloy baths for the electroless deposition |
| JPS6267192A (ja) * | 1985-09-17 | 1987-03-26 | Shinko Electric Ind Co Ltd | 電解ニツケル−ホウ素合金めつき浴 |
| IT1256851B (it) * | 1992-01-21 | 1995-12-27 | Procedimento per promuovere l'aderenza fra diversi strati nella fabbricazione di circuiti stampati multistrato. e composizioni per l'attuazione di tale procedimento. | |
| US5721014A (en) * | 1995-12-19 | 1998-02-24 | Surface Tek Specialty Products, Inc. | Composition and method for reducing copper oxide to metallic copper |
| US5750087B1 (en) * | 1996-06-27 | 1999-12-14 | Mine Safety Appliances Co | Process for the reduction of copper oxide |
-
1997
- 1997-07-10 JP JP53606398A patent/JP3431170B2/ja not_active Expired - Fee Related
- 1997-07-10 KR KR10-1998-0710167A patent/KR100375589B1/ko not_active Expired - Fee Related
- 1997-07-10 DE DE69726752T patent/DE69726752T2/de not_active Expired - Fee Related
- 1997-07-10 EP EP97935217A patent/EP0938447B1/en not_active Expired - Lifetime
- 1997-07-10 AT AT97935217T patent/ATE256085T1/de not_active IP Right Cessation
- 1997-07-10 CA CA002254106A patent/CA2254106C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP3431170B2 (ja) | 2003-07-28 |
| EP0938447A4 (https=) | 1999-09-01 |
| KR20000065233A (ko) | 2000-11-06 |
| KR100375589B1 (ko) | 2003-06-09 |
| JP2000502518A (ja) | 2000-02-29 |
| ATE256085T1 (de) | 2003-12-15 |
| DE69726752T2 (de) | 2004-11-11 |
| EP0938447B1 (en) | 2003-12-10 |
| CA2254106A1 (en) | 1999-01-10 |
| EP0938447A1 (en) | 1999-09-01 |
| DE69726752D1 (de) | 2004-01-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |