JPS6141988B2 - - Google Patents
Info
- Publication number
- JPS6141988B2 JPS6141988B2 JP13664783A JP13664783A JPS6141988B2 JP S6141988 B2 JPS6141988 B2 JP S6141988B2 JP 13664783 A JP13664783 A JP 13664783A JP 13664783 A JP13664783 A JP 13664783A JP S6141988 B2 JPS6141988 B2 JP S6141988B2
- Authority
- JP
- Japan
- Prior art keywords
- copper
- acid
- bisimidazole
- water
- solution
- 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
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 13
- 229910052802 copper Inorganic materials 0.000 claims description 13
- 239000010949 copper Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- SQZLLYMZDZQMRH-UHFFFAOYSA-N 5-methyl-4-[(5-methyl-2-undecyl-1h-imidazol-4-yl)methyl]-2-undecyl-1h-imidazole Chemical compound N1C(CCCCCCCCCCC)=NC(CC2=C(NC(CCCCCCCCCCC)=N2)C)=C1C SQZLLYMZDZQMRH-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- AZUHIVLOSAPWDM-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-1h-imidazole Chemical compound C1=CNC(C=2NC=CN=2)=N1 AZUHIVLOSAPWDM-UHFFFAOYSA-N 0.000 description 10
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000004310 lactic acid Substances 0.000 description 4
- 235000014655 lactic acid Nutrition 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BIUXMENMIKBKFP-UHFFFAOYSA-N CO.CC(O)C(O)=O Chemical compound CO.CC(O)C(O)=O BIUXMENMIKBKFP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- -1 bisimidazole copper complex 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
- 238000007598 dipping method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- XDAHMMVFVQFOIY-UHFFFAOYSA-N methanedithione;sulfane Chemical compound S.S=C=S XDAHMMVFVQFOIY-UHFFFAOYSA-N 0.000 description 1
- 239000000693 micelle Substances 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
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Organic Chemistry (AREA)
- Chemical Treatment Of Metals (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
Description
【発明の詳細な説明】
本発明は、銅の表面を４・4′−メチレン−ビス
−（２−ウンデシル−５−メチルイミダゾール）
またはその塩を含む溶液で接触処理し、金属表面
に化成被膜を形成せしめることを特徴とする銅の
防錆方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention provides a method for treating the surface of copper with 4,4'-methylene-bis-(2-undecyl-5-methylimidazole).
The present invention relates to a method for preventing rust of copper, which is characterized by contact treatment with a solution containing copper or its salt to form a chemical conversion film on the surface of the metal.
銅の表面は大気中で次第に汚染され、やがて本
来の色調と光択を完全に失い特に硫化水素や二硫
化炭素のような硫黄化合物を含む雰囲気中では速
やかに褐色化するものである。 Copper surfaces gradually become contaminated in the atmosphere, eventually completely losing their original color and photosensitivity, and quickly turning brown, especially in atmospheres containing sulfur compounds such as hydrogen sulfide and carbon disulfide.
以上のことは銅金属製品の商品価値を著しく低
下させる。本発明者等は下記一般式で示される
４・4′−メチレン−ビス−（２−ウンデシル−５
−メチルイミダゾール）またはその塩を含む溶液
で銅の表面を接触処理することによつて顕著な防
錆効果をうることを見出した。 The above causes a significant decrease in the commercial value of copper metal products. The present inventors have discovered that 4,4'-methylene-bis-(2-undecyl-5
It has been found that a remarkable antirust effect can be obtained by contact-treating the surface of copper with a solution containing (-methylimidazole) or a salt thereof.
本発明の実施に適する溶剤は塩の場合は水ある
いはアルコール類である。 Suitable solvents for carrying out the invention are water or alcohols in the case of salts.
アルコール類は次のようなものである。メタノ
ール、エタノール、イソプロパノール、ｎ−プロ
パノール、エチレングリコール、エチレン−グリ
コール−モノ−メチルエーテル。また該ビスイミ
ダゾールの場合は前記アルコール類とクロロホル
ム又はクロロセンが使用される。 Alcohols are as follows. Methanol, ethanol, isopropanol, n-propanol, ethylene glycol, ethylene-glycol-mono-methyl ether. In the case of bisimidazole, the alcohols and chloroform or chlorocene are used.
本発明の実施に適する塩は水溶性でなければな
らない。そのような塩は該ビスイミダゾールと有
機酸あるいは無機酸のいずれかより形成されるも
のである。酸の役割は該ビスイミダゾールを水に
溶解させることにある。従つて、そのような役割
を果たすものであればいかなる酸も使用出来る。
該ビスイミダゾール塩は銅金属と接触すると、銅
金属面上にビスイミダゾール銅錯体を形成し、そ
れが原動力となつて、ミセルが更に形成され最終
的に表面はビスイミダゾール被膜で蔽われ、これ
が防錆効果を発揮する。 Salts suitable for the practice of this invention must be water soluble. Such salts are formed from the bisimidazole and either organic or inorganic acids. The role of the acid is to dissolve the bisimidazole in water. Therefore, any acid that fulfills such a role can be used.
When the bisimidazole salt comes into contact with copper metal, it forms a bisimidazole copper complex on the copper metal surface, which acts as a driving force to further form micelles, and finally the surface is covered with a bisimidazole film, which prevents this. Demonstrates rust effect.
他方、役目を果たした（即ち解離した）酸成分
は水溶液中に移行する。 On the other hand, the acid components that have fulfilled their role (ie, dissociated) migrate into the aqueous solution.
代表的な有機酸として酢酸、グリコール酸、蓚
酸、琥珀酸、乳酸が使用され、無機酸として塩
酸、硫酸、燐酸、硝酸が使用される。 Typical organic acids used are acetic acid, glycolic acid, oxalic acid, succinic acid, and lactic acid, while hydrochloric acid, sulfuric acid, phosphoric acid, and nitric acid are used as inorganic acids.
本発明の実施態様について次に述べる。銅の表
面を酸洗浄あるいはサンドペーパーによつて仕上
げ、引続き該ビスイミダゾールまたはその塩を含
む溶液中に浸漬する。あるいは浸漬の代わりに該
溶液を塗布または噴霧してもよい。 Embodiments of the present invention will be described next. The surface of the copper is finished by acid washing or sandpaper, and then immersed in a solution containing the bisimidazole or its salt. Alternatively, the solution may be applied or sprayed instead of dipping.
以上の処理は、０〜100℃の温度範囲で実施出
来るが室温下で行うのが最も簡単で望ましい。 The above treatment can be carried out at a temperature range of 0 to 100°C, but it is easiest and most desirable to carry out it at room temperature.
前述の溶液濃度は0.01〜5.0wt％で特に0.1〜
2.0wt％が望ましい。 The concentration of the solution mentioned above is 0.01~5.0wt%, especially 0.1~
2.0wt% is desirable.
処理時間は１分間以上あれば、それで充分であ
る。後処理は水洗、乾燥の順で行われる。勿論、
水洗を省略することは出来る。 A treatment time of 1 minute or more is sufficient. Post-treatment is performed in the order of washing with water and drying. Of course,
Washing with water can be omitted.
次に該ビスイミダゾールの特性を示す。 Next, the characteristics of the bisimidazole will be shown.
融点：182〜183℃
νｋｂｒcm〓：2925、2855、1618、1531、1465、1445、
1420（第一吸収）1375、1316、1037、918、
833、713
NMR（CD3OD）
δ：3.65、ｓ、2H（メチレン基）
：2.56、ｔ、4H（α−メチレン）
：2.00、ｓ、6H（メチル基）
：1.61、ｍ、4H（β−メチレン）
：1.27、ｍ、32H（ウンデシル基）
：0.89、ｔ、6H（ウンデシル基の末端メ
チル）
Mass：ｍ／e484（M+）、329、357、343、249、
240
以下、実施例によつて本発明の実施態様を具体
的に説明する。Melting point: 182-183℃ ν kbr cm〓: 2925, 2855, 1618, 1531, 1465, 1445,
1420 (first absorption) 1375, 1316, 1037, 918,
833, 713 NMR (CD 3 OD) δ: 3.65, s, 2H (methylene group): 2.56, t, 4H (α-methylene): 2.00, s, 6H (methyl group): 1.61, m, 4H (β- Methylene): 1.27, m, 32H (undecyl group): 0.89, t, 6H (terminal methyl of undecyl group) Mass: m/e484 (M + ), 329, 357, 343, 249,
240 Hereinafter, embodiments of the present invention will be specifically explained with reference to Examples.
実施例 １
市販75％乳酸を水分除去のため減圧濃縮し、残
留物をメタノールにとかし、乳酸メタノール溶液
を調整した。該温溶液にPHが6.5になる迄４・
4′−メチレン−ビス−（２−ウンデシル−５−メ
チルイミダゾール）を加えたのち、該溶液を減圧
濃縮し、油状物質をえた。このものは放置により
固化した。該固化物をアセトンで３回反復再結
し、該ビスイミダゾールの乳酸塩（m.p.99〜100
℃）をえた。乳酸塩のNMR（CD3OD）は次の如
くである。Example 1 Commercially available 75% lactic acid was concentrated under reduced pressure to remove water, and the residue was dissolved in methanol to prepare a lactic acid methanol solution. 4. Add to the warm solution until the pH reaches 6.5.
After addition of 4'-methylene-bis-(2-undecyl-5-methylimidazole), the solution was concentrated under reduced pressure to give an oil. This solidified by standing. The solidified product was reconstituted three times with acetone to obtain the lactate salt of bisimidazole (mp99-100).
℃) was obtained. The NMR (CD 3 OD) of lactate is as follows.
δ：5.07、ｓ、2H（乳酸の水酸基）：4.02、ｑ、
2H（乳酸のα−プロトン）：3.85、ｓ、2H
（メチレン基）：2.77、ｔ、4H（ウンデシル基
のα−メチレン）：2.19、ｓ、6H（イミダゾ
ールの５位メチル基）：1.68、ｍ、4H（ウン
デシル基のβ−メチレン）：1.27、ｍ、32H
（ウンデシル基）：0.89、ｔ、6H（ウンデシル
基の末端メチル）
サンドペーパーで磨き、ベンゼンで脱脂した幅
３cmの銅張積層板を該乳酸塩１ｇと水99ｇよりな
る水溶液（やや白濁を呈する）に室温で５分間浸
漬し該板を取出して水洗乾燥し、空中放置して表
面が変色するまでに要する日数（変色日数）を調
べた。なお、この観察は二硫化炭素製造工場内の
未処理対照板が一日で変色する場所で行われた。
変色日数は30日であつた。δ: 5.07, s, 2H (hydroxyl group of lactic acid): 4.02, q,
2H (α-proton of lactic acid): 3.85, s, 2H
(Methylene group): 2.77, t, 4H (α-methylene of undecyl group): 2.19, s, 6H (5-position methyl group of imidazole): 1.68, m, 4H (β-methylene of undecyl group): 1.27, m ,32H
(Undecyl group): 0.89, t, 6H (terminal methyl of undecyl group) A 3 cm wide copper clad laminate polished with sandpaper and degreased with benzene is mixed with an aqueous solution of 1 g of the lactate and 99 g of water (slightly cloudy) The board was immersed in water for 5 minutes at room temperature, taken out, washed with water, dried, and left in the air to determine the number of days required for the surface to change color (number of days for discoloration). This observation was conducted at a location in a carbon disulfide manufacturing plant where an untreated control board would change color within a day.
The number of days for discoloration was 30 days.
実施例 ２
該ビスイミダゾール１ｇを水99ｇに投じ、50〜
60℃で撹拌し乍ら酢酸１mlを加え、PH３以下を示
す酢酸塩水溶液をえた。該溶液を50〜60℃に保
ち、実施例１の如く前処理した銅張積層板をそれ
に１分間浸漬したのち水洗乾燥した。Example 2 1 g of the bisimidazole was poured into 99 g of water, and 50 ~
While stirring at 60°C, 1 ml of acetic acid was added to obtain an acetate aqueous solution having a pH of 3 or less. The solution was maintained at 50-60°C, and the copper-clad laminate pretreated as in Example 1 was immersed in the solution for 1 minute, then washed with water and dried.
このものの変色日数は25日であつた。対照片の
それは１日であつた。 The number of days the product changed color was 25 days. That of the control piece was 1 day.
実施例 ３
該ビスイミダゾール１ｇをエタノール99ｇにと
かし、かくしてえられた溶液を実施例１の如く前
処理した銅張積層板に室温で噴霧した。このもの
の変色日数は30日であつた。対照片のそれは１日
であつた。Example 3 1 g of the bisimidazole was dissolved in 99 g of ethanol and the solution thus obtained was sprayed onto a copper clad laminate pretreated as in Example 1 at room temperature. The number of days for discoloration of this product was 30 days. That of the control piece was 1 day.
Claims (1)
メチレン−ビス−（２−ウンデシル−５−メチル
イミダゾール）またはその塩を含む溶液で接触処
理し、金属表面に化成被膜を形成せしめることを
特徴とする銅の防錆方法。 一般式 [Scope of Claims] 1. The surface of copper is 4.4′- expressed by the following general formula.
A method for preventing rust on copper, which comprises contacting with a solution containing methylene-bis-(2-undecyl-5-methylimidazole) or a salt thereof to form a chemical conversion film on a metal surface. general formula
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13664783A JPS6026673A (en) | 1983-07-25 | 1983-07-25 | Method for keeping copper and copper alloy from rusting |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13664783A JPS6026673A (en) | 1983-07-25 | 1983-07-25 | Method for keeping copper and copper alloy from rusting |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6026673A JPS6026673A (en) | 1985-02-09 |
| JPS6141988B2 true JPS6141988B2 (en) | 1986-09-18 |
Family
ID=15180208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13664783A Granted JPS6026673A (en) | 1983-07-25 | 1983-07-25 | Method for keeping copper and copper alloy from rusting |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6026673A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10876662B2 (en) | 2017-03-15 | 2020-12-29 | Novelis Inc. | Corrugated heat protection tube and methods of making the same |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
1983
- 1983-07-25 JP JP13664783A patent/JPS6026673A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10876662B2 (en) | 2017-03-15 | 2020-12-29 | Novelis Inc. | Corrugated heat protection tube and methods of making the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6026673A (en) | 1985-02-09 |
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