JPH03182585A - High performance laminating adhesive agent based on epoxy - Google Patents
High performance laminating adhesive agent based on epoxyInfo
- Publication number
- JPH03182585A JPH03182585A JP1315132A JP31513289A JPH03182585A JP H03182585 A JPH03182585 A JP H03182585A JP 1315132 A JP1315132 A JP 1315132A JP 31513289 A JP31513289 A JP 31513289A JP H03182585 A JPH03182585 A JP H03182585A
- Authority
- JP
- Japan
- Prior art keywords
- component
- isocyanate
- polyester
- epoxy
- reaction
- 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
- 239000004593 Epoxy Substances 0.000 title claims abstract description 39
- 239000012939 laminating adhesive Substances 0.000 title abstract description 3
- 239000003795 chemical substances by application Substances 0.000 title 1
- 229920000728 polyester Polymers 0.000 claims abstract description 36
- 239000012948 isocyanate Substances 0.000 claims abstract description 32
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 32
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- 239000000853 adhesive Substances 0.000 claims abstract description 19
- 230000001070 adhesive effect Effects 0.000 claims abstract description 19
- 239000000463 material Substances 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 229920003986 novolac Polymers 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims description 17
- 239000002131 composite material Substances 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 7
- 239000011888 foil Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229920001721 polyimide Polymers 0.000 claims description 4
- 229920006158 high molecular weight polymer Polymers 0.000 claims description 3
- 229920000647 polyepoxide Polymers 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 239000007767 bonding agent Substances 0.000 abstract 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- 239000004035 construction material Substances 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229910014033 C-OH Inorganic materials 0.000 description 2
- 229910014570 C—OH Inorganic materials 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000011889 copper foil Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 101710176122 28 kDa heat- and acid-stable phosphoprotein Proteins 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000238557 Decapoda Species 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 102100027336 Regenerating islet-derived protein 3-alpha Human genes 0.000 description 1
- 230000008436 biogenesis Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 238000007763 reverse roll coating Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
見1Bケ考JL
過去25年間にわたる電子回路産業の急激な発展は、高
性能構成材料の開発も促進させてきた。しかしなから、
高性能構成材料の開発は、特に自動車産業及び軍事産業
に見られる厳しい環境条件でこれらの構成材料を互いに
接着できるような高性能の接着材料及びシステムの開発
にはつなからなかった。現在入手できる接着材料及びシ
ステムは、例えば剥離強さ、耐薬品性、耐湿性、高温安
定性、特にZ軸方向での寸法安定性及び易加工性等の特
性に関する要件の一部を満たすが、通常は前記特性の1
つ又はそれ以上に関する1つ又はそれ以上の要件を満た
すことはできない。DETAILED DESCRIPTION OF THE INVENTION The rapid development of the electronic circuit industry over the past 25 years has also facilitated the development of high performance construction materials. However, because
The development of high performance construction materials has not led to the development of high performance adhesive materials and systems that can bond these construction materials together in the harsh environmental conditions found in the automotive and military industries in particular. Currently available adhesive materials and systems meet some of the requirements regarding properties such as, for example, peel strength, chemical resistance, moisture resistance, high temperature stability, dimensional stability especially in the Z-axis direction and ease of processing. Usually one of the above characteristics
One or more of the requirements for one or more items cannot be met.
そのため、易使用性を保持しなから、厳しい環境条件に
適した特性の要件を総て満たす接着材料の必要が唱えら
れてきた。Therefore, there has been a need for an adhesive material that satisfies all the requirements for properties suitable for harsh environmental conditions while also maintaining ease of use.
4艷へ44
本発明の目的の1つは改良された接着材料(adhes
ive material)を提供することにある。4. One of the objects of the present invention is to provide improved adhesive materials.
ive material).
本発明の特徴の1つは、電子分野の構成材料に使用する
のに適した改良接着材料を提供(provicle)す
ることにある。One of the features of the invention is to provide an improved adhesive material suitable for use in construction materials in the electronic field.
本発明の別の特徴は、接着に2つの段階からなる反応プ
ロセスを必要とする接着材料を提供することにある。Another feature of the present invention is to provide an adhesive material that requires a two-step reactive process for bonding.
本発明の更に別の特徴は、高性能の接着材料を提供すべ
く、2段階反応を用いてイソシアネート成分とポリエス
テル成分と1種類以上のエポキシ成分とを組合わせるこ
とにある。Yet another feature of the present invention is the use of a two-step reaction to combine the isocyanate component, the polyester component, and one or more epoxy components to provide a high performance adhesive material.
本発明の前記特徴及び他の特徴は、可視性のビスーエピ
エポキシ類及び硬質のノボラックエポキシ類から選択し
た少なくとも1種類のエポキシ成分と、少なくとも1種
類の高分子量ポリエステル成分とをイソシアネート硬化
成分と共に組合わせることによって達成される。即ち、
イソシアネート硬化成分及びポリエステル成分を第1反
応段階で互いに反応させ、第1反応段階で得られたイソ
シアネート/ポリエステル化合物をエポキシ成分と組合
わせるのである。このようにして成分を組合わせたもの
は、積層の表面又は別の第1面に適用(塗布)し得る。These and other features of the present invention provide that at least one epoxy component selected from visible bis-epiepoxies and hard novolac epoxies and at least one high molecular weight polyester component are combined with an isocyanate curing component. This is achieved by matching. That is,
The isocyanate curing component and the polyester component are reacted with each other in a first reaction step, and the isocyanate/polyester compound obtained in the first reaction step is combined with the epoxy component. The combination of components in this manner may be applied (coated) to the surface of the laminate or to another first side.
この第1面に第2面を接触させて第2段階の反応を生起
させれば、前述のごとき高性能接合剤(bond)が形
成される。When the second surface is brought into contact with the first surface and a second stage reaction occurs, a high performance bond as described above is formed.
本発明の特徴は以下の説明でより明らかにされよう。The features of the present invention will become clearer from the following description.
楚□シm
本発明の材料組成物は、例えばCe1anese Ep
iRez−5132のような可撓性ビス−エピ類及び例
えばDon D、E、N、438のような硬質ノボラッ
ク類から選択した少なくとも1種類、好ましくは2種類
以上のエポキシ成分と、DuPont社の49002も
しくはDeSot。The material composition of the present invention is, for example, Ce1anese Ep.
at least one, preferably two or more, epoxy components selected from flexible bis-epis such as iRez-5132 and rigid novolacs such as Don D, E, N, 438 and DuPont's 49002 Or DeSot.
社の301樹脂システムのような少なくとも1種類の高
分子量ポリエステル成分と、Upjohn社のPAP1
135もしくはMobay社のMondur MRSの
ようなイソシアネート硬化成分とを含む。at least one high molecular weight polyester component, such as Upjohn's 301 resin system and Upjohn's PAP1 resin system.
135 or Mobay's Mondur MRS.
本発明の硬化処理では、先ず下記の公知の反応シーケン
スに従って、イソシアネート成分とポリエステル成分の
末端のヒドロキシル基とを反応させる。In the curing treatment of the present invention, first, the isocyanate component and the terminal hydroxyl group of the polyester component are reacted according to the following known reaction sequence.
HO−(R) −OB
+
ocN(c、o4−(co2)]]
n−C−
0
前記式中、(R)xはアルコールタイプのヒドロキシル
末端基官能性を有する高分子量ポリエステルの反復単位
を表す、この反応は室温ではゆっくりと進行し、組成物
を約250°Fに加熱するとより速く進行する。HO-(R)-OB+ocN(c,o4-(co2)]]n-C-0 where (R)x represents a repeating unit of a high molecular weight polyester with alcohol-type hydroxyl end group functionality. As shown, this reaction proceeds slowly at room temperature and more rapidly when the composition is heated to about 250 degrees Fahrenheit.
第2反応は本発明独自のものであり、形成され基とを下
記のように反応させることからなる。The second reaction is unique to the invention and consists of reacting the groups formed as follows.
−C−OH
Rx
−C−OH
−C−H
0−(C)12)−0−C−N−[C山−(CH2)]
。-C-OH Rx -C-OH -C-H 0-(C)12)-0-C-N-[Mount C-(CH2)]
.
前記式中、 Rxは下記の構造をもつビス エビ及び/ 又はノボラックエポキシを表す。In the above formula, Rx is a bis with the following structure shrimp and/or Or represents novolac epoxy.
本発明の接着材料は、実施態様の1つとして、下記の成
分を含む。In one embodiment, the adhesive material of the present invention includes the following components.
Dupont 49002ベースからなるポリエステル
樹脂を固体含量17〜20%で90重量%の塩化メチレ
ンと10重量%のシクロヘキサンとの溶媒混合物中に溶
解したもの;
Dow DEN 438−EK85からなるエポキシノ
ボラックを固体含量85重量%でメチルエチルケトンに
溶解したちの;
固体含量100%のCe1anese Epi−Rez
5132からなるビスーエピエボキシ;
Mobay社から商品名Mondur MRSとして市
販されている多官能性イソシアネートからなる硬化成分
。Polyester resin consisting of Dupont 49002 base dissolved in a solvent mixture of 90% by weight methylene chloride and 10% by weight cyclohexane at a solids content of 17-20%; an epoxy novolac consisting of Dow DEN 438-EK85 at a solids content of 85%. Ce1anese Epi-Rez dissolved in methyl ethyl ketone in weight%; solids content 100%
5132; a curing component consisting of a polyfunctional isocyanate commercially available from Mobay under the trade name Mondur MRS.
これらの成分は、接着コーティング組成物を形成すべく
、下記の2つの方法のいずれかで組合わせることができ
る。These ingredients can be combined to form an adhesive coating composition in either of two ways.
方法1) 固体含量で80重量%のポリエステル成分と
、固体含量で10重量%のエポキシノボラックと、固体
含量で10重量%のビスーエピエボキシと、1.2重量
部のイソシアネートとを撹拌せずに開放容器中に導入す
る0次いでこの組成物を1〜5分間、十分に撹拌する。Method 1) 80% by weight of a polyester component, 10% by weight of an epoxy novolac, a 10% by weight of a bis-epoxy, and 1.2 parts by weight of an isocyanate are mixed without stirring. The composition is then thoroughly stirred for 1 to 5 minutes before introduction into an open container.
その後、容器を密栓して30分間静置し、イソシアネー
ト/ポリエステル反応を生起させる。Thereafter, the container is tightly capped and left to stand for 30 minutes to allow the isocyanate/polyester reaction to occur.
方法2〉 ポリエステル及びイソシアネートを組合わせ
、十分に混合し、エポキシを加えるまえに室温で30分
以上靜装置てイソシアネート/ヒドロキシル反応を生起
させる。Method 2> Combine the polyester and isocyanate, mix well, and allow the isocyanate/hydroxyl reaction to occur in a quiet device at room temperature for at least 30 minutes before adding the epoxy.
ポリイミドフィルム上に厚さ1m1lの乾燥コーティン
グを形成すべく、前記方法のいずれかで形成した接着コ
ーティング組成物をリバースロールコーティング法を用
いて塗布する。75フイートの3ゾーン炉により25f
pm(74−17分〉、212°FT乾燥(即ち溶媒除
去)を行う0次いで、コーティングした前記支持体(s
ubstrate)を102.銅ホイルの処理面、即ち
(接着性を向上させるために)Oak CMC−111
化合物で処理した面に接触させる。このようにして組合
わせたポリイミドフィルム及び銅ホイルを、1つの連続
的操作の一部分として、塗布機と貼合わせ機とを組合わ
せた操作ステーションで、80psi(ボンド/平方イ
ンチ)〜120psiの圧力を加えなから300°F〜
325°Fに加熱する。得られた複合体を6インチの芯
にロール状に巻き上げ、室温で1〜7日間放置し、その
後下記のように後硬化処理する。The adhesive coating composition formed by any of the methods described above is applied using a reverse roll coating method to form a 1 ml thick dry coating on the polyimide film. 25f with 75ft 3 zone furnace
The coated support (s
102. Copper foil treated side, i.e. (to improve adhesion) Oak CMC-111
Contact with a surface treated with the compound. The thus combined polyimide film and copper foil are subjected to pressures of 80 psi (bond per square inch) to 120 psi at a combined coating and laminating machine operating station as part of one continuous operation. 300°F~
Heat to 325°F. The resulting composite is rolled up onto a 6 inch core and left at room temperature for 1 to 7 days before being post cured as described below.
150°Fで2時間
275°Fで2時間
350”Fで2時間
得られた複合構造体を^NSI/IPC−FC−232
B及び241Bの方法でテストした結果、表■のような
性質を示した。The resulting composite structure was heated at 150°F for 2 hours, 275°F for 2 hours, and 350”F for 2 hours at NSI/IPC-FC-232.
As a result of testing using the methods of B and 241B, the properties shown in Table 2 were shown.
PLI −直線インチ当たりのボンド(pounds
perleal inch)
MEK−メチルエチルケトン
TOL=)ルエン
IP^−イソプロピルアルコール
T111= )リクロロエチレン
MC−塩化メチレン
この好ましい実施例では、ポリエステル化合物がヒドロ
キシルを末端基とする高分子量ポリマーであり、硬化用
化合物がポリマー状イソシアネートである。この好まし
い実施例では、可撓性ビス−エピエポキシ化合物及び硬
質ノボラックエポキシ化合物の特性が両方共得られるよ
うに、これらの化合物を組合わせて使用する。第2反応
では、■
/ \
C−C基とが副生物の発生を伴わずに完全に架橋される
。PLI - pounds per linear inch
perleal inch) MEK-Methyl Ethyl Ketone TOL=) Luene IP^-Isopropyl Alcohol T111=) Lichloroethylene MC-Methylene Chloride In this preferred embodiment, the polyester compound is a hydroxyl-terminated high molecular weight polymer and the curing compound is It is a polymeric isocyanate. In this preferred embodiment, a combination of flexible bis-epiepoxy compounds and rigid novolak epoxy compounds is used to provide the properties of both. In the second reaction, ■ / \ C--C groups are completely crosslinked without generation of by-products.
本発明の方法を使用すれば、これまで知られていなかっ
た独自の硬化メカニズムにより、様々な特性を極めてバ
ランス良く示し且つ優れたZ軸支定性を有する新規な接
着システムを得ることができる。本発明はより特定的に
は、現在入手できるいずれのシステムよりも優れた全体
的特性を有すると共に、Z軸支定性も優れている可撓性
ボンドブライを製造すべく、連続的に加工でき且つ副生
物の発生を伴わずに硬化できるエポキシベースの新規な
貼合わせ用接着剤(aclheseve)を提供する。Using the method of the present invention, a novel adhesive system can be obtained which exhibits a very well-balanced variety of properties and has excellent Z-axis stability due to a unique and hitherto unknown curing mechanism. More specifically, the present invention provides a continuous processable and secondary method for producing flexible bonded blies with superior overall properties and superior Z-axis support than any currently available system. A novel epoxy-based laminating adhesive (aclheseve) is provided that can be cured without biogenesis.
本発明の接着材料は、フィルムからなる支持体(例えば
ポリイミド)、ホイルからなる支持体く例えば銅〉及び
ハードボードからなる支持体く例えばFR4(ガラス繊
維含浸)ハードボード)に適用し得る。The adhesive material of the invention can be applied to substrates made of films (eg polyimide), foils (eg copper) and hardboards (eg FR4 (glass fiber impregnated) hardboard).
ある。be.
Claims (17)
ステル化合物と反応させるステップ及び、前記イソシア
ネート/ポリエステル反応段 階で得られたイソシアネート/ポリエステル成分をビス
−エピエポキシ成分及びノボラックエポキシ成分から選
択した少なくとも1種類のエポキシ成分と反応させるス
テップを含む接着材料の提供方法。(1) reacting the isocyanate component with at least one type of polyester compound, and converting the isocyanate/polyester component obtained in the isocyanate/polyester reaction step to at least one type of epoxy compound selected from a bis-epoxy component and a novolac epoxy component; A method of providing an adhesive material comprising the step of reacting with a component.
1種類のエポキシ成分と反応させる前に、前記イソシア
ネート/ポリエステル成分と前記エポキシ化合物とを混
合し、得られた混合物を接着材料の必要な場所に塗布す
るステップも含む請求項1に記載の提供方法。(2) prior to reacting the isocyanate/polyester component with at least one epoxy component, the step of mixing said isocyanate/polyester component with said epoxy compound and applying the resulting mixture to the required location of the adhesive material; The providing method according to claim 1, comprising:
複数の支持体の間に前記混合物を塗布してこれらの支持
体を接着させるステップも含む請求項2に記載の提供方
法。3. The method of claim 2, further comprising the step of: (3) applying the mixture between a plurality of supports selected from film, foil, and hardboard to adhere the supports.
用し、少なくとも1種類のエポキシ化合物を90重量%
〜50重量%使用する請求項1に記載の提供方法。(4) Use 50% to 90% by weight of a polyester compound and 90% by weight of at least one type of epoxy compound
The providing method according to claim 1, wherein ~50% by weight is used.
する高分子量ポリマーから選択する請求項1に記載の提
供方法。(5) The method according to claim 1, wherein the polyester compound is selected from hydroxyl-terminated high molecular weight polymers.
分との混合物を250°F〜400°Fの温度で加熱す
ることによって、エポキシ成分とイソシアネート/ポリ
エステル成分とを反応させる請求項1に記載の提供方法
。6. The method of claim 1, wherein the epoxy component and the isocyanate/polyester component are reacted by heating the mixture of the epoxy component and the isocyanate/polyester component at a temperature of 250 DEG F. to 400 DEG F.
いに接着した2つの面を有する製品。(7) A product having two surfaces adhered to each other according to the method of providing an adhesive material according to claim 1.
、フィルム対フィルム接合、ホイル対ホイル接合又はホ
イル対フィルム接合による複合製品。(8) A composite product of film-to-film bonding, foil-to-foil bonding, or foil-to-film bonding having surfaces bonded according to the method of claim 2.
シ成分とを混合してから、これらの成分を反応させる請
求項1に記載の提供方法。(9) The method according to claim 1, wherein the isocyanate component, the polyester component, and the epoxy component are mixed and then reacted.
すべき面に適用するための接着剤複合体。(10) An adhesive composite prepared by the method according to claim 2 for application to surfaces to be adhered to each other.
も1種類のエポキシ成分との反応が、形成されたウレタ
ン結合の−N−基と前記エポキシ成分の▲数式、化学式
、表等があります▼基との反応を含む請求項1に記載の
製造方法。(11) The reaction between the isocyanate/polyester component and at least one type of epoxy component includes the reaction between the -N- group of the formed urethane bond and the ▲ mathematical formula, chemical formula, table, etc. ▼ group of the epoxy component. The manufacturing method according to claim 1.
第1構造体の第1面及び前記第2構造体の第1面を互い
に接着させる接着材料とを含む複合構造体であって、前
記接着材料が、 イソシアネート成分と、 ポリエステル成分と、 ビス−エピエポキシ類及びノボラックエポ キシ類から選択した少なくとも1種類のエポキシ成分と
を含む複合構造体。(12) A composite structure including at least a first structure, a second structure, and an adhesive material for bonding a first surface of the first structure and a first surface of the second structure to each other. , wherein the adhesive material comprises: an isocyanate component; a polyester component; and at least one epoxy component selected from bis-epoxies and novolac epoxies.
ム、金属ホイル及びハードボードから選択される請求項
12に記載の複合構造体。13. The composite structure of claim 12, wherein the first structure and the second structure are selected from polyimide film, metal foil, and hardboard.
る高分子量ポリマーであり、このポリエステル成分及び
イソシアネート成分が、少なくとも1種類のエポキシ成
分との反応の前に反応し合う請求項13に記載の複合構
造体。(14) The composite structure according to claim 13, wherein the polyester component is a high molecular weight polymer having hydroxyl terminal groups, and the polyester component and the isocyanate component react with each other before reacting with at least one epoxy component. .
応の結果得られたイソシアネート/ポリエステル成分と
少なくとも1種類のエポキシ成分とを、該イソシアネー
ト/ポリエステル成分と前記少なくとも1種類のエポキ
シ成分との反応の前に、第1構造体の第1面と第2構造
体の第2面との間に塗布する請求項14に記載の複合構
造体。(15) The isocyanate/polyester component obtained as a result of the reaction between the polyester component and the isocyanate component and at least one type of epoxy component, before the reaction between the isocyanate/polyester component and the at least one type of epoxy component, 15. The composite structure according to claim 14, wherein the composite structure is applied between the first surface of the first structure and the second surface of the second structure.
も1種類のエポキシ成分との反応が生起するように25
0°F〜400°Fの温度で加熱する請求項15に記載
の複合構造体。(16) 25 to cause the reaction between the isocyanate/polyester component and at least one epoxy component to occur.
16. The composite structure of claim 15, wherein the composite structure is heated at a temperature of 0<0>F to 400<0>F.
も1種類のエポキシ成分との反応が、イソシアネート/
ポリエステルの−N−基とエポキシ成分の▲数式、化学
式、表等があります▼基との反応を含む請求項16に記
載の複合構造体。(17) The reaction between the isocyanate/polyester component and at least one type of epoxy component
17. The composite structure according to claim 16, comprising a reaction between the -N- group of the polyester and the ▲ mathematical formula, chemical formula, table, etc. ▼ group of the epoxy component.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA 2004130 CA2004130A1 (en) | 1989-11-29 | 1989-11-29 | High performance epoxy based laminating adhesive |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH03182585A true JPH03182585A (en) | 1991-08-08 |
Family
ID=4143657
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP1315132A Pending JPH03182585A (en) | 1989-11-29 | 1989-12-04 | High performance laminating adhesive agent based on epoxy |
Country Status (2)
Country | Link |
---|---|
JP (1) | JPH03182585A (en) |
CA (1) | CA2004130A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6002065A (en) * | 1988-04-20 | 1999-12-14 | Norian Corporation | Kits for preparing calcium phosphate minerals |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2133839A1 (en) * | 1992-04-06 | 1993-10-14 | Thomas F. Gardeski | A high performance epoxy based laminating adhesive |
-
1989
- 1989-11-29 CA CA 2004130 patent/CA2004130A1/en not_active Abandoned
- 1989-12-04 JP JP1315132A patent/JPH03182585A/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6002065A (en) * | 1988-04-20 | 1999-12-14 | Norian Corporation | Kits for preparing calcium phosphate minerals |
Also Published As
Publication number | Publication date |
---|---|
CA2004130A1 (en) | 1991-05-29 |
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