JPH06279456A - Novel azole silane compound and its production and metal surface-treating agent using the same - Google Patents
Novel azole silane compound and its production and metal surface-treating agent using the sameInfo
- Publication number
- JPH06279456A JPH06279456A JP7173693A JP7173693A JPH06279456A JP H06279456 A JPH06279456 A JP H06279456A JP 7173693 A JP7173693 A JP 7173693A JP 7173693 A JP7173693 A JP 7173693A JP H06279456 A JPH06279456 A JP H06279456A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- silane compound
- formula
- treating agent
- azole
- 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.)
- Pending
Links
Classifications
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/22—Secondary treatment of printed circuits
- H05K3/28—Applying non-metallic protective coatings
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/38—Improvement of the adhesion between the insulating substrate and the metal
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、金属表面の防錆の改善
を行うための表面処理剤、特にはプリント回路用銅張積
層板等に用いられる銅箔用表面処理剤として有用な新規
なアゾール系シラン化合物及びその製造方法、並びにそ
の用途に関する。FIELD OF THE INVENTION The present invention relates to a novel surface treatment agent for improving the rust prevention of a metal surface, particularly a novel surface treatment agent for copper foil used for copper clad laminates for printed circuits. The present invention relates to an azole silane compound, a method for producing the same, and uses thereof.
【０００２】[0002]
【従来の技術】プリント回路用の銅張積層板は銅箔を紙
−フェノール樹脂含浸基材やガラス−エポキシ樹脂含浸
基材等に加熱、加圧して積層して形成され、これをエッ
チングして回路網を形成し、これに半導体装置等の素子
を搭載することにより電子機器用のボードが作られる。
これらの過程では、基材との接着、加熱、酸やアルカリ
液への浸漬、レジストインクの塗布、ハンダ付け等が行
われるため、銅箔には各種の性能が要求される。たとえ
ば、通常Ｍ面（粗化面、以下同様）と呼称されている基
材と接着される側には主として基材との接着性、耐薬品
性等が要求され、又Ｍ面の反対側の通常Ｓ面（光沢面、
以下同様）と呼称されている側には主として耐熱性、耐
湿性等が要求されている。又これらの両面には保管時に
銅箔の酸化変色のないことも要求されている。これらの
要求を満たすために、銅箔のＭ面には黄銅層形成処理
（特公昭５１−３５７１１号公報、同５４−６７０１号
公報）、Ｍ、Ｓ双方の面にはクロメート処理、亜鉛また
は酸化亜鉛とクロム酸化物とからなる亜鉛−クロム基混
合物被覆処理等（特公昭５８−７０７７号公報）が行わ
れている。A copper clad laminate for a printed circuit is formed by laminating a copper foil on a paper-phenol resin-impregnated base material or glass-epoxy resin-impregnated base material by heating and pressurizing it. A board for electronic equipment is made by forming a circuit network and mounting an element such as a semiconductor device on the circuit network.
In these processes, adhesion with a base material, heating, immersion in an acid or alkaline solution, application of resist ink, soldering, etc. are performed, so that various performances are required for the copper foil. For example, the side that is usually called the M surface (roughened surface, the same applies below) is mainly required to have adhesiveness with the base material, chemical resistance, etc. Usually S side (glossy surface,
The same shall apply hereinafter) is mainly required to have heat resistance and moisture resistance. It is also required that the copper foils on both sides of the copper foil do not undergo oxidative discoloration during storage. In order to satisfy these requirements, a brass layer forming treatment (Japanese Patent Publication No. 51-57711, 54-6701) on the M side of the copper foil, chromate treatment, zinc or oxidation on both sides of M and S. A coating treatment of a zinc-chromium group mixture consisting of zinc and chromium oxide (Japanese Patent Publication No. 58-7077) has been carried out.
【０００３】[0003]
【発明が解決しようとする課題】しかしながら、前記し
たように最近プリント回路が緻密化しているので、使用
されるプリント回路用銅箔に要求される特性はますます
厳しくなっている。本発明は、こうした要請に対応でき
る、すなわち、金属表面に対する防錆作用が高い新規な
シラン化合物、その製造方法、及びそれを用いた新規な
金属表面処理剤、特に銅箔用表面処理剤を提供すること
を目的とするものである。However, since the printed circuit has been densified recently as described above, the characteristics required for the copper foil for the printed circuit used have become more and more severe. The present invention provides a novel silane compound capable of meeting such demands, that is, having a high anticorrosive action on a metal surface, a method for producing the same, and a novel metal surface treating agent using the same, particularly a surface treating agent for copper foil. The purpose is to do.
【０００４】[0004]
【課題を解決するための手段】本発明者は、鋭意研究を
進めた結果、特定のアゾール環を有するシラン化合物が
金属表面に対し優れた防錆作用を有することを見出し
た。As a result of intensive studies, the present inventor has found that a silane compound having a specific azole ring has an excellent rust preventive action on a metal surface.
【０００５】本発明は、かかる知見に基づきなされたも
のであり、その要旨は、 （１）下記一般式（１）で表される新規アゾール系シラ
ン化合物、The present invention has been made based on such findings, and the gist thereof is (1) a novel azole silane compound represented by the following general formula (1),
【０００６】[0006]
【化３】 [Chemical 3]
【０００７】（ただし、一般式（１）において、Ｒ1，
Ｒ2は炭素数が１〜３のアルキル基、ｎは０〜３）、 （２）下記一般式（２）で表される２−メルカプト−１
−メチルイミダゾールと下記一般式（３）で表される３
−グリシドキシプロピルシラン化合物とを、８０〜２０
０℃で反応させることを特徴とする前記１記載のアゾー
ル系シラン化合物の製造方法。(However, in the general formula (1), R 1 ,
R 2 is an alkyl group having 1 to 3 carbon atoms, n is 0 to 3), (2) 2-mercapto-1 represented by the following general formula (2).
-Methylimidazole and 3 represented by the following general formula (3)
-Glycidoxypropyl silane compound,
The method for producing an azole-based silane compound according to the above 1, wherein the reaction is carried out at 0 ° C.
【０００８】[0008]
【化４】 [Chemical 4]
【０００９】（ただし、一般式（３）において、Ｒ1，
Ｒ2は炭素数が１〜３のアルキル基、ｎは０〜３） （３）前記１記載の一般式（１）で表されるアゾール系
シラン化合物の少なくとも１種を有効成分とする金属表
面処理剤。 （４）前記１記載の一般式（１）で表されるアゾール系
シラン化合物の少なくとも１種を有効成分とする銅箔用
表面処理剤にある。(However, in the general formula (3), R 1 ,
R 2 is an alkyl group having 1 to 3 carbon atoms, n is 0 to 3) (3) A metal surface containing at least one azole-based silane compound represented by the general formula (1) described in 1 above as an active ingredient. Processing agent. (4) A surface treatment agent for copper foil, which contains at least one azole-based silane compound represented by the general formula (1) described in 1 above as an active ingredient.
【００１０】以下に本発明をさらに詳細に説明する。上
記一般式（１）におけるＲ1又はＲ2は炭素数が１〜３の
アルキル基であるが、特には合成の容易性からメチル
基、エチル基が好適である。またｎは０〜３である。The present invention will be described in more detail below. R 1 or R 2 in the above general formula (1) is an alkyl group having 1 to 3 carbon atoms, and a methyl group and an ethyl group are particularly preferable from the viewpoint of easy synthesis. Further, n is 0 to 3.
【００１１】本発明の上記アゾール系シラン化合物
（１）は、式（２）で表される２−メルカプト−１−メ
チルイミダゾールと一般式（３）で表される３−グリシ
ドキシプロピルシラン化合物とを、８０〜２００℃で反
応させることにより製造することができる。その反応を
式で示すと次のようになる。The azole silane compound (1) of the present invention is a 2-mercapto-1-methylimidazole represented by the formula (2) and a 3-glycidoxypropylsilane compound represented by the general formula (3). Can be produced by reacting and at 80 to 200 ° C. The reaction is expressed by the following equation.
【００１２】[0012]
【化５】 [Chemical 5]
【００１３】（上記式中、Ｒ1及びＲ2は炭素数１〜３の
アルキル基、ｎは０〜３を表す） 上記一般式（３）で表される３−グリシドキシプロピル
シラン化合物は、３−グリシドキシプロピルトリアルコ
キシシラン、３−グリシドキシプロピルジアルコキシア
ルキルシラン、３−グリシドキシプロピルアルコキシジ
アルキルシラン、３−グリシドキシプロピルトリアルキ
ルシランであり、これらのうちとくに好ましいものを挙
げれば、３−グリシドキシプロピルトリアルコキシシラ
ンとしては、３−グリシドキシプロピルトリメトキシシ
ラン、３−グリシドキシプロピルトリエトキシシラン、
また３−グリシドキシプロピルジアルコキシアルキルシ
ランとしては、３−グリシドキシプロピルジメトキシメ
チルシラン、３−グリシドキシプロピルアルコキシジア
ルキルシランとしては、３−グリシドキシプロピルエト
キシジメチルシラン、３−グリシドキシプロピルトリア
ルキルシランとしては、３−グリシドキシプロピルトリ
エチルシラン等である。(Wherein R 1 and R 2 are alkyl groups having 1 to 3 carbon atoms, and n is 0 to 3) The 3-glycidoxypropylsilane compound represented by the general formula (3) is , 3-glycidoxypropyltrialkoxysilane, 3-glycidoxypropyldialkoxyalkylsilane, 3-glycidoxypropylalkoxydialkylsilane, 3-glycidoxypropyltrialkylsilane, and particularly preferred among these. Examples of 3-glycidoxypropyltrialkoxysilane include 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane,
Further, 3-glycidoxypropyldialkoxyalkylsilane is 3-glycidoxypropyldimethoxymethylsilane, and 3-glycidoxypropylalkoxydialkylsilane is 3-glycidoxypropylethoxydimethylsilane, 3-glycid Examples of the xypropyltrialkylsilane include 3-glycidoxypropyltriethylsilane and the like.
【００１４】上記２−メルカプト−１−メチルイミダゾ
ールと３−グリシドキシプロピルシラン化合物との反応
は、８０〜２００℃の温度に加熱した２−メルカプト−
１−メチルイミダゾールに０．１〜１０モル倍量の３−
グリシドキシプロピルシラン化合物を滴下させながら行
うと良く、反応時間は５分〜２時間程度で十分である。
この反応は特には溶媒を必要とはしないが、クロロホル
ム、ジオキサン、メタノール、エタノール等の有機溶剤
を反応溶媒として用いてもよい。尚、この反応は、水分
を嫌うので、水分が混入しないように、乾燥した窒素、
アルゴン等の水分を含まない気体の雰囲気下で行うこと
が好ましい。The reaction between the 2-mercapto-1-methylimidazole and the 3-glycidoxypropylsilane compound is carried out by heating the 2-mercapto-1-methylimidazole compound to a temperature of 80 to 200 ° C.
0.1- to 10-fold molar amount of 3-to 1-methylimidazole
It is advisable to carry out the reaction while dropping the glycidoxypropylsilane compound, and a reaction time of about 5 minutes to 2 hours is sufficient.
This reaction does not require a solvent in particular, but an organic solvent such as chloroform, dioxane, methanol or ethanol may be used as a reaction solvent. In addition, since this reaction does not like water, dry nitrogen,
It is preferable to carry out under an atmosphere of a gas containing no water such as argon.
【００１５】上記アゾール系シラン化合物を金属表面処
理剤として用いる場合、その対象金属には特に制限はな
い。たとえば銅、亜鉛及びこれらの合金等の表面処理剤
として有用である。しかし、銅の表面処理剤として用い
ることが好適であり、特にはプリント回路用銅張積層板
等に用いられる銅箔の表面処理剤として用いると本発明
の効果を十分に発揮することができる。この銅箔には銅
箔の表面を粗面化処理したもの、銅箔に黄銅層形成処理
したもの、クロメート処理したもの、亜鉛−クロム基混
合物被覆処理したもの等も包含される。When the above-mentioned azole type silane compound is used as a metal surface treating agent, the target metal is not particularly limited. For example, it is useful as a surface treatment agent for copper, zinc and alloys thereof. However, it is suitable to be used as a surface treatment agent for copper, and particularly when used as a surface treatment agent for a copper foil used for a copper clad laminate for printed circuits, the effects of the present invention can be sufficiently exhibited. The copper foil includes a copper foil whose surface has been roughened, a copper foil which has been subjected to a brass layer formation treatment, a chromate treatment, a zinc-chromium group mixture coating treatment, and the like.
【００１６】上記アゾール系シラン化合物は、少なくと
もその一種をそのまま直接金属表面に塗布してもよい
が、メタノール、エタノール等のアルコール類、又はそ
れらと水との混合溶液、更には、アセトン、酢酸エチ
ル、トルエン等の溶剤で０．００１〜２０重量％になる
ように希釈し、この液に金属を浸漬させる方法で塗布す
ることが簡便で好ましい。尚、このアゾール系シラン化
合物は単独で用いてもよいが、他の防錆剤等と混合して
用いてもよい。At least one of the above-mentioned azole type silane compounds may be directly applied to the metal surface as it is, but alcohols such as methanol and ethanol, or a mixed solution thereof with water, and further acetone and ethyl acetate. It is convenient and preferable to dilute the solution with a solvent such as toluene to a concentration of 0.001 to 20% by weight and immerse the metal in this solution. The azole-based silane compound may be used alone, or may be mixed with another rust preventive agent and used.
【００１７】[0017]
【実施例】アゾール系シラン化合物の合成 （２−メルカプト−１−メチルイミダゾールと３−グリ
シドキシプロピルトリメトキシシランとの反応） 実施例１ ２−メルカプト−１−メチルイミダゾール５．７ｇ
（０．０５ｍｏｌ）を１２０℃で加温し、アルゴン雰囲
気下で撹拌しながら、３−グリシドキシプロピルトリメ
トキシシラン１１．８ｇ（０．０５ｍｏｌ）を３０分間
かけて滴下した。滴下終了後、さらに１２０℃の温度で
１時間反応させた。Example Synthesis of azole silane compound ( reaction of 2-mercapto-1-methylimidazole with 3-glycidoxypropyltrimethoxysilane) Example 1 5.7 g of 2-mercapto-1-methylimidazole
(0.05 mol) was heated at 120 ° C., and 11.8 g (0.05 mol) of 3-glycidoxypropyltrimethoxysilane was added dropwise over 30 minutes while stirring under an argon atmosphere. After the dropping was completed, the reaction was further performed at a temperature of 120 ° C. for 1 hour.
【００１８】反応生成物は透明な黄色の粘稠な液体（以
下「化合物１」という）として得られた。この生成物は
透明な黄色の粘性液体で数週間以上ゲル化せず安定であ
った。またアルコール、クロロホルム、テトラヒドロフ
ラン等に可溶であり、ゲルパーミエーションクロマトグ
ラフィーにより単一成分であることを確認した。The reaction product was obtained as a transparent yellow viscous liquid (hereinafter referred to as "compound 1"). The product was a clear yellow viscous liquid and was stable without gelation for more than several weeks. It was also soluble in alcohol, chloroform, tetrahydrofuran and the like, and was confirmed to be a single component by gel permeation chromatography.
【００１９】又、この一部を採取して、1Ｈ−ＮＭＲで
分析した結果、−ＳＨピークは完全に消失しており、反
応は完全に進行していた。又ＩＲよりＯＨ基の伸縮振動
のピークも確認され、これからも上記した反応が進行し
たことがわかった（図１，２）。また、ＭＳスペクトル
の分析結果を以下に示す。A part of this was taken and analyzed by 1 H-NMR. As a result, the --SH peak had completely disappeared and the reaction had proceeded completely. Further, from IR, a peak of stretching vibration of OH group was also confirmed, and it was found that the above-mentioned reaction proceeded from this point (FIGS. 1 and 2). The results of MS spectrum analysis are shown below.
【００２０】ＭＳ；３５０（Ｍ+） これらの結果から、上記化合物１は上記一般式（１）に
おいてＲ1がメチル、ｎが３である下記式（１−１）の
構造を有することがわかった。MS; 350 (M +) From these results, it is found that the above compound 1 has a structure of the following formula (1-1) in which R 1 is methyl and n is 3 in the above formula (1). It was
【００２１】[0021]
【化６】 [Chemical 6]
【００２２】次に、以上生成したアゾール系シラン（化
合物１）を銅箔の表面処理剤として評価した。評価方法
は以下の通りである。Next, the azole silane (Compound 1) thus produced was evaluated as a surface treatment agent for copper foil. The evaluation method is as follows.
【００２３】耐湿性試験 電解銅箔（厚さ７５μｍ、４．５×４．５ｃｍ）をアセ
トンで脱脂し、３％の硫酸水溶液で洗浄した。この銅箔
の光沢面に、前記で得られた化合物１のアゾール系シラ
ン化合物を６重量％の濃度になるようにメタノールに溶
解し、この溶液をスピンコーターで塗布し、０．３μｍ
のアゾール系シラン化合物の薄膜を作成し、これを試験
片とした。 Moisture resistance test Electrolytic copper foil (thickness 75 μm, 4.5 × 4.5 cm) was degreased with acetone and washed with a 3% sulfuric acid aqueous solution. On the shiny side of this copper foil, the azole silane compound of Compound 1 obtained above was dissolved in methanol to a concentration of 6% by weight, and this solution was applied by a spin coater to give a thickness of 0.3 μm.
A thin film of the azole-based silane compound was prepared and used as a test piece.
【００２４】この試験片を温度８０℃、湿度９５％の恒
温恒湿槽に２４時間入れ、変色の程度で耐湿性を評価し
た。比較のため、上記アゾール系シラン化合物に代え
て、シランカップリング剤として市販されている３−グ
リシドキシプロピルトリメトキシシラン（以下単に「エ
ポキシシラン」と言う）及びアゾール系化合物として市
販されている２−メルカプト−１−メチルイミダゾール
のメタノール溶液を同様に０．３μｍ塗布した銅箔及び
何も塗布しない銅箔（以下「ブランク」とする）につい
て同様に評価し、結果を表１に示した。The test piece was placed in a thermo-hygrostat having a temperature of 80 ° C. and a humidity of 95% for 24 hours, and the moisture resistance was evaluated by the degree of discoloration. For comparison, instead of the azole-based silane compound, 3-glycidoxypropyltrimethoxysilane (hereinafter simply referred to as “epoxysilane”) that is commercially available as a silane coupling agent and azole-based compound is commercially available. Similarly, a copper foil coated with a methanol solution of 2-mercapto-1-methylimidazole in a thickness of 0.3 μm and a copper foil coated with nothing (hereinafter referred to as “blank”) were evaluated in the same manner, and the results are shown in Table 1.
【００２５】[0025]
【表１】 [Table 1]
【００２６】（注）耐湿性試験；５：変色なし、４：わ
ずかに変色、３：少し変色、２：橙色又は黄色に変色、
１：黒褐色に変色 以上の結果から本発明の化合物が、金属の表面処理剤と
して耐湿性（防錆作用）に優れていることがわかる。(Note) Moisture resistance test; 5: No discoloration, 4: Slight discoloration, 3: Slight discoloration, 2: Orange or yellow discoloration,
1: Discoloration to blackish brown It can be seen from the above results that the compound of the present invention has excellent moisture resistance (anticorrosion effect) as a metal surface treatment agent.
【００２７】[0027]
【発明の効果】本発明の新規なアゾール系シラン化合物
は金属表面処理剤、特に銅箔用表面処理剤として有用な
もので、防錆作用に優れるという効果を有するものであ
る。INDUSTRIAL APPLICABILITY The novel azole-based silane compound of the present invention is useful as a metal surface treating agent, especially as a surface treating agent for copper foil, and has an effect of excellent rust prevention.
【図１】化合物１の1Ｈ−ＮＭＲスペクトルFIG. 1 1 H-NMR spectrum of Compound 1
【図２】同ＩＲスペクトルFIG. 2 Same IR spectrum
───────────────────────────────────────────────────── フロントページの続き (72)発明者 荻野 幸男 埼玉県戸田市新曽南３丁目17番35号 株式 会社日鉱共石内 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Yukio Ogino 3-17-35, Shinsōnan, Toda City, Saitama Prefecture Nikko Kyoishi Co., Ltd.
Claims (4)
ル系シラン化合物。 【化１】 （ただし、一般式（１）において、Ｒ1，Ｒ2は炭素数が
１〜３のアルキル基、ｎは０〜３）1. A novel azole silane compound represented by the following general formula (1). [Chemical 1] (However, in the general formula (1), R 1 and R 2 are alkyl groups having 1 to 3 carbon atoms, and n is 0 to 3)
−１−メチルイミダゾールと下記一般式（３）で表され
る３−グリシドキシプロピルシラン化合物とを、８０〜
２００℃で反応させることを特徴とする請求項１記載の
アゾール系シラン化合物の製造方法。 【化２】 （ただし、一般式（３）において、Ｒ1，Ｒ2は炭素数が
１〜３のアルキル基、ｎは０〜３）2. A 2-mercapto-1-methylimidazole represented by the following formula (2) and a 3-glycidoxypropylsilane compound represented by the following general formula (3),
The method for producing an azole-based silane compound according to claim 1, wherein the reaction is performed at 200 ° C. [Chemical 2] (However, in the general formula (3), R 1 and R 2 are alkyl groups having 1 to 3 carbon atoms, and n is 0 to 3)
アゾール系シラン化合物の少なくとも１種を有効成分と
する金属表面処理剤。3. A metal surface treating agent comprising at least one azole-based silane compound represented by the general formula (1) as an active ingredient.
アゾール系シラン化合物の少なくとも１種を有効成分と
する銅箔用表面処理剤。4. A surface treatment agent for a copper foil, which contains at least one azole-based silane compound represented by the general formula (1) as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7173693A JPH06279456A (en) | 1993-03-30 | 1993-03-30 | Novel azole silane compound and its production and metal surface-treating agent using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7173693A JPH06279456A (en) | 1993-03-30 | 1993-03-30 | Novel azole silane compound and its production and metal surface-treating agent using the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06279456A true JPH06279456A (en) | 1994-10-04 |
Family
ID=13469111
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7173693A Pending JPH06279456A (en) | 1993-03-30 | 1993-03-30 | Novel azole silane compound and its production and metal surface-treating agent using the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH06279456A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102498600A (en) * | 2009-09-11 | 2012-06-13 | Jx日矿日石金属株式会社 | Copper foil for lithium ion battery current collector |
| CN102640333A (en) * | 2009-11-05 | 2012-08-15 | Jx日矿日石金属株式会社 | Copper foil for collector of lithium ion battery |
| JP2021528378A (en) * | 2018-06-18 | 2021-10-21 | アトテック ドイチェランド ゲーエムベーハー | Azole silane compound |
-
1993
- 1993-03-30 JP JP7173693A patent/JPH06279456A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102498600A (en) * | 2009-09-11 | 2012-06-13 | Jx日矿日石金属株式会社 | Copper foil for lithium ion battery current collector |
| CN102640333A (en) * | 2009-11-05 | 2012-08-15 | Jx日矿日石金属株式会社 | Copper foil for collector of lithium ion battery |
| JP2021528378A (en) * | 2018-06-18 | 2021-10-21 | アトテック ドイチェランド ゲーエムベーハー | Azole silane compound |
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