JPS5941358A - Composition for heat-resistant adhesive - Google Patents
Composition for heat-resistant adhesiveInfo
- Publication number
- JPS5941358A JPS5941358A JP15002082A JP15002082A JPS5941358A JP S5941358 A JPS5941358 A JP S5941358A JP 15002082 A JP15002082 A JP 15002082A JP 15002082 A JP15002082 A JP 15002082A JP S5941358 A JPS5941358 A JP S5941358A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- resin
- weight
- composition
- alkyl
- 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
- H05K3/38—Improvement of the adhesion between the insulating substrate and the metal
- H05K3/386—Improvement of the adhesion between the insulating substrate and the metal by the use of an organic polymeric bonding layer, e.g. adhesive
Landscapes
- Epoxy Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
【発明の詳細な説明】
〔発明の技術分野〕
本発明は、耐熱性、平田耐熱性および接着性に優れた接
着剤用組成物に関する。DETAILED DESCRIPTION OF THE INVENTION [Technical Field of the Invention] The present invention relates to an adhesive composition having excellent heat resistance, Hirata heat resistance, and adhesiveness.
従来から熱硬化形の接着剤としては、フェノール樹脂や
エボキン樹脂あるいはポリアミド系樹脂を主体とするも
のが多く用いられているが、これらの樹脂は熱変形温度
が低いため、接着剤としての使用条目−が限定されると
いう欠点があった。す々わちフェノール樹脂系の接着剤
においては、１４０℃以上の温度域ｆ・でおいては耐熱
性ＶＣ乏しく、°また縮合反応により硬化するため、硬
化時に発泡がおこり面間の接着には適さないという難点
があった。Conventionally, thermosetting adhesives mainly made of phenolic resin, Evoquin resin, or polyamide resin have been widely used, but these resins have low heat distortion temperatures, so their use as adhesives has been limited. - had the disadvantage of being limited. In the case of phenolic resin adhesives, heat-resistant VC is poor in the temperature range of 140°C or higher, and since they harden through a condensation reaction, foaming occurs during curing, resulting in poor adhesion between surfaces. The problem was that it was not suitable.
更にエポキシ樹脂系の接着剤においては、樹脂のガラス
転移点が低いため、耐熱性に乏しく、接着剤としての操
作性および保存安定性に劣るという難点があった。Furthermore, epoxy resin adhesives have disadvantages in that they have poor heat resistance and poor operability and storage stability as adhesives because the resin has a low glass transition point.
本発明はこれら従来から難点を解消し、アルミニウムの
ような軽量複合構造体用の接着剤とじて特に好適な耐熱
接着剤用組成物を提供することを目的としている。It is an object of the present invention to overcome these conventional difficulties and to provide a composition for a heat-resistant adhesive that is particularly suitable as an adhesive for lightweight composite structures such as aluminum.
本発明の耐熱接着剤用組ＪＪＭ’、物は、（ト）（イ）
シマレイミド化合物と（ロ）アミンフェノールとＣ→エ
ポキシ化合物とに）イミダゾール化合物とを必須成分と
する熱硬化性樹脂９５〜３０重ｉ％と、（Ｂ）ポリビニ
ルホルマール樹脂５〜７０重量係とから成る組成物であ
る。The heat-resistant adhesive set JJM' of the present invention is (G) (B)
Consisting of 95 to 30% by weight of a thermosetting resin whose essential components are a simaleimide compound, (B) an amine phenol, a C→epoxy compound, and an imidazole compound, and (B) a polyvinyl formal resin of 5 to 70% by weight. It is a composition.
本発明における（Ａ）の熱硬化性樹脂の配合成分の一つ
である（イ）のシマレイミド化合物としては、次の一般
式で表されるものが適している。As the simaleimide compound (A), which is one of the components of the thermosetting resin (A) in the present invention, those represented by the following general formula are suitable.
（式中、Ｒは水素原子又はアルキル基’ｆｃ、Ｒ２は一
〇−、−ＣＨ−、−８ｏ２−又け−５−Ｓ−から選択さ
れた２価の有機基ヲ、Ｒ３は水素原子又は・・ロゲン原
子を表す。）
このようなシマレイミド化合物の具体例とじてｔま、４
．４’−ジフェニルメタンシマレイミド、４．４’−ジ
フェニルニーデルシマレイミド、４．４’−ジフェニル
スルノ」ンジマレイミド、Ｎ、Ｎ′−シナオビス（Ｎ−
７エニルマレイミド〕、ポリ（フェニルメチレン）シマ
レイミド等を挙げることができる。(In the formula, R is a hydrogen atom or an alkyl group 'fc, R2 is a divalent organic group selected from 10-, -CH-, -8o2- or -5-S-, R3 is a hydrogen atom or (Represents a rogene atom.) Specific examples of such simalimide compounds include t, 4.
．． 4'-diphenylmethanesimaleimide, 4,4'-diphenylneedlesimaleimide, 4,4'-diphenylsulno'ndimaleimide, N,N'-cyanobis(N-
7enylmaleimide], poly(phenylmethylene)simalimide, and the like.
また、他の配合成分の一つである（口）アミンフェノー
ルと（７ては、υ４ ｔ／’ｒ 、−駁゛式で表さ７′
するものが適している。In addition, one of the other compounded ingredients, (1) amine phenol (7 is υ4 t/'r, -7'
What is appropriate is what you do.
！’
（ｒ（、中１４＆ｉ、水系原子、ハロゲンｕ子又はアル
キルｈ（から力畦択塾ｆする１薗の原子まｒけ基を表す
。）
このようなアミツノエノールの具体例としてｒ／１、例
えしｌ’ ｏ −、ｍ−又汀ｐ−異性ｆ本のアミンフェ
ノールお↓ひアミノクレゾール、２−アミノ−４−クロ
ロフェノール、しζ””” ’ ＝’ｒ＾−↓
。! ' (r (, middle 14&i, represents a water-based atom, a halogen atom, or an atom merging group from an alkyl h). A specific example of such an aminoenol is r/1 , for example l' o -, m- and p-isomer f amine phenol ↓ aminocresol, 2-amino-4-chlorophenol, ζ"""'='r^-↓
.
２−アミノ−４−り一ロクレゾールのような谷独直侯基
異伯一体を含有するアミノフェノール、アミンクレゾー
ル、アミノクロロフェノール、アミノブロムフェノール
等を挙げることができる。Examples thereof include aminophenols containing 2-amino-4-ri-rocresol, aminecresols, aminochlorophenols, aminobromophenols, and the like.
さらに配合成分の一つである（ハ）エポキシ化合物とし
ては、ビスフェノール形の芳香族系のもの、シクロヘキ
セン誘導体形の脂肪族系のもの、ノボラ、り形分子構造
内にトリアジン核ヲ冶する多官能性エポキシ樹脂などヲ
準げることができる。なかでザ後者の多官能性エポキシ
樹脂を使用すると、前二者によるときに比べ、耐熱性を
一層向上させることができる。Furthermore, (c) epoxy compounds, which are one of the compounded components, include aromatic ones in the form of bisphenols, aliphatic ones in the form of cyclohexene derivatives, and polyfunctional epoxy compounds that have a triazine nucleus in the novola-shaped molecular structure. It can also be used as a synthetic epoxy resin. When the latter polyfunctional epoxy resin is used, the heat resistance can be further improved compared to when the former two are used.
さらにもう一つの配合成分であるに）イミダゾール化合
物としては、次の一般式で表されるものが適している。As the imidazole compound (another ingredient), those represented by the following general formula are suitable.
７
（式中Ｒ５−Ｒ８ハ、水素原子又はアルキル基から選択
される同−又は異なる１価の原子又は基を表す。９
このようなイミダゾール化合物の具体例としては、例え
ば２−エチル−４−メチルイミダゾール。7 (In the formula, R5-R8 represent the same or different monovalent atoms or groups selected from hydrogen atoms or alkyl groups.9 Specific examples of such imidazole compounds include, for example, 2-ethyl-4- Methylimidazole.
２−メチルイミダゾール、１−ベンジル−２−メチルイ
ミダゾールなどがある。Examples include 2-methylimidazole and 1-benzyl-2-methylimidazole.
」二記各成分の配合比は、（イ）のシマレイミド化合物
１００重量部に対して、（ロ）のアミンフェノールが１
０〜３０重量部、（ハ）のエポキシ化合物が２０〜１０
０重量部、に）のイミダゾール化合物が０．１〜２重量
部の範囲が適している。The blending ratio of each component in (B) is 100 parts by weight of the simaleimide compound (A) to 1 part by weight of the amine phenol in (B).
0 to 30 parts by weight, 20 to 10 parts of the epoxy compound (c)
A range of 0.1 to 2 parts by weight of the imidazole compound is suitable.
本発明においては、以上の４つの配合成分を全て混合し
て反応させ、熱硬化性樹脂を製造するがその混合および
反応の順序は一通りに限定されない。しかし々から通常
は、（イ）のシマレイミド化合物の１種又は２種以上と
、（ロ）のアミンフェノールの１種又は２種以上とをま
ず付加反応させ、次いでこの付加反応物に（ハ）のエポ
キシ化合物とに）のイミダゾール化合物を混合し反応さ
せる方法が採られる。In the present invention, a thermosetting resin is produced by mixing and reacting all of the above four ingredients, but the order of mixing and reaction is not limited to one particular order. However, usually, one or more of the simaleimide compounds in (a) and one or more of the amine phenols in (b) are first subjected to an addition reaction, and then this addition reaction product is reacted with (c). A method is adopted in which the epoxy compound (1) and the imidazole compound (2) are mixed and reacted.
本発明の組成物は、このようにして得られた熱硬化性樹
脂に、予めジメチルホルムアミド、ジメチルアセトアミ
ド、Ｎ−″メチルー２−ピロリドンのような有機極性溶
媒、或いにアセトン、メチルエチルケトン、ジオキサン
、エチレングリコール。The composition of the present invention is prepared by adding an organic polar solvent such as dimethylformamide, dimethylacetamide, N-''methyl-2-pyrrolidone to the thermosetting resin thus obtained, or acetone, methyl ethyl ketone, dioxane, ethylene glycol.
モノメチルエーテルアセテート、シクロヘキサンのよう
な低沸点溶媒に溶解させたポリビニルホルマール樹脂を
均一に混合して得られる。その混合割合は、熱硬化性樹
脂９５〜３０重量％に対し、ポリビニルホルマール５〜
７０重量％の割合とする。It is obtained by uniformly mixing polyvinyl formal resin dissolved in a low boiling point solvent such as monomethyl ether acetate or cyclohexane. The mixing ratio is 5 to 30% by weight of polyvinyl formal to 95 to 30% by weight of thermosetting resin.
The proportion is 70% by weight.
配合の比率をこのような範囲に限定したのは、熱硬化性
樹脂が３０重量係未満でＦｉ（従ってポリビニルホルマ
ール樹脂の割合が７０重量％を超える場合には）高温時
における接着強度が悪くなり、逆に９５重量％を超える
と、（ポリビニルホルマール樹脂５重量饅未ｉ）接着層
の可撓性が低くなり、゛また均一な層を作ることができ
ないためである。The reason for limiting the blending ratio to this range is that if the thermosetting resin is less than 30% by weight, the adhesive strength at high temperatures will deteriorate (if the proportion of polyvinyl formal resin exceeds 70% by weight). On the other hand, if it exceeds 95% by weight, the flexibility of the adhesive layer decreases and a uniform layer cannot be formed.
以上のようにして得られる本発明の耐熱接着剤用組成物
は耐熱性、半田耐熱性および接着性に優れ、軽量複合構
造体用の接着剤として好適なものである。The heat-resistant adhesive composition of the present invention obtained as described above has excellent heat resistance, soldering heat resistance, and adhesive properties, and is suitable as an adhesive for lightweight composite structures.
次に本発明の実施例について記載する。 Next, examples of the present invention will be described.
実施例１〜４
第１表に示す重量割合の４，４′−ジフェニルメタンシ
マレイミドとｍ−アミノフェノールを、ジオキサンを反
応溶媒とし１２０〜１３０’Ｃで５時間反応させた後、
こｆＬにエポキシ樹脂と２−エチル−４−メチルイミダ
ゾールを加え、次いで予めジオキサンに溶解させたポリ
ビニルホルマー樹脂を均一［混合して、固形分３０重量
係の樹脂溶液を得た。Examples 1 to 4 After reacting 4,4'-diphenylmethanesimalimide and m-aminophenol in the weight proportions shown in Table 1 at 120 to 130'C using dioxane as a reaction solvent for 5 hours,
Epoxy resin and 2-ethyl-4-methylimidazole were added to this fL, and then polyvinylformer resin previously dissolved in dioxane was uniformly mixed to obtain a resin solution with a solid content of 30% by weight.
次に得られた溶液を、通常の塗布装置を用いて電解銅箔
の表面に塗布し、１３０’Ｃで１０分間乾燥して３６μ
の１９．さの樹脂層を形成し、その」二に厚さ２２１１
１ｉのアルミニウム板を重ね、これを熱板プレスにより
１８０℃ｌ（ｇ／ＣＪの条件で１時間加熱し、アルミニ
ウム基板を製造した。このアルミニウム基板の特性を次
の方法により測定した。Next, the obtained solution was applied to the surface of the electrolytic copper foil using an ordinary coating device, and dried at 130'C for 10 minutes to form a 36μ
19. Form a resin layer with a thickness of 2211 mm.
1i aluminum plates were stacked and heated for 1 hour at 180° C.l (g/CJ) using a hot plate press to produce an aluminum substrate. The properties of this aluminum substrate were measured by the following method.
（剥離強反）
１ｃ１ｎｌＩ＠に切断したものを、常温で、或いは１８
０℃の恒温槽内で、９０度方向に５Ｑ ｗｙｐ／ｍｉｎ
の速度で引張り、銅箔とアルミニウム板が剥ガｔした瞬
間の強度を測った。(Strong peeling) Cut into 1c1nlI @ at room temperature or 18
5Q wyp/min in a 90 degree direction in a constant temperature oven at 0℃
The strength was measured at the moment the copper foil and aluminum plate were peeled off.
（半田耐熱性）
２５ｍｍ角に切断した試料を２６０’Ｃおよび３００℃
の半１１槽に浮かべ、銅箔にふくれが発生するまでの時
間を測定した。(Soldering heat resistance) Samples cut into 25 mm squares were heated at 260'C and 300°C.
The copper foil was floated in a half tank, and the time until blisters appeared on the copper foil was measured.
測定結果を第１表の下段に示した。The measurement results are shown in the lower part of Table 1.
比較例１〜３
第１表に示す配合割合によって実施例１〜４と同様に行
いかつ、特性を測定し、その結果を第１表に示した。Comparative Examples 1 to 3 Comparative Examples 1 to 3 were conducted in the same manner as Examples 1 to 4 using the blending ratios shown in Table 1, and the characteristics were measured, and the results are shown in Table 1.
実施例５〜１０
第２表に示す割合のＮ、Ｎ’−メチレンビスフェニルマ
レイミドとｐ−アミンフェノールを、ジオキサン溶媒中
１２０〜１３０℃の温度で５時間反応させた後、エポキ
シ樹脂と２−エチル−４−メチルイミダゾールを加え、
次いでこれに予めメチルエチルケトンに溶解させたポリ
ビニルアルコール樹脂ヲ均一に混合して、固形分３５重
量係の樹脂溶液を得た。Examples 5 to 10 After reacting N,N'-methylenebisphenylmaleimide and p-amine phenol in the proportions shown in Table 2 at a temperature of 120 to 130°C in a dioxane solvent for 5 hours, epoxy resin and 2- Add ethyl-4-methylimidazole,
Next, a polyvinyl alcohol resin preliminarily dissolved in methyl ethyl ketone was mixed uniformly into this to obtain a resin solution having a solid content of 35% by weight.
次に、得られた溶液を、塗布装置により、５０μ厚さの
カプトン（米国デュポン社ポリイミドフィルムの商品名
）の両面に塗布し、１２０℃で２０分間乾燥させた。こ
れを１００騎Ｘ ２５ ＴＲｍ Ｘ ｌ ｍｍの軟鋼板
２枚の間に１０ｙｔｒｍオーバーラツプさせてはさみ込
み熱板プレスによ！ｌ） １８０℃、１０に９／ｎＪの
条件で３０分間加熱した後、２００℃で５時間アフター
キュアを行った。得られた基板の引張せん断強度を、高
滓製作所のオートグランＩＳ −２０００’ｉ用いて測
定した。その結果を第２表の下段に示した。Next, the obtained solution was applied to both sides of a 50 μm thick Kapton (trade name of a polyimide film manufactured by DuPont, USA) using a coating device and dried at 120° C. for 20 minutes. This was sandwiched between two mild steel plates of 100 x 25 TRm x 1 mm with an overlap of 10 ytrm, and then pressed using a hot plate press! l) After heating at 180° C. and 10 to 9/nJ for 30 minutes, after-curing was performed at 200° C. for 5 hours. The tensile shear strength of the obtained substrate was measured using Autogran IS-2000'i manufactured by Takasu Seisakusho. The results are shown in the lower part of Table 2.
比較例４〜６
第２表に示す割合によって実施例５〜１ｏと同様に行い
、特性を測定して結果を得たので第２表に示した。Comparative Examples 4 to 6 Comparative Examples 4 to 6 were conducted in the same manner as Examples 5 to 1o using the ratios shown in Table 2, and the characteristics were measured and the results are shown in Table 2.
本発明の組成物は第１表および第２表かられかるように
剥離強度、半田耐熱性およびせん断引張強度に優れてい
た。As shown in Tables 1 and 2, the composition of the present invention was excellent in peel strength, soldering heat resistance, and shear tensile strength.
Claims (1)
は水素原子又は・・ロゲン原子を表す。うで示されるン
マレイミ ト化合物と、 ←）一般式 （式中Ｒは、水素原子、・・ロゲン原 子又はアルキル基７１１ら選択される１価の原子又は基
を表す。）で示されるア ミノフェノールと、 （ハ）エポキシ化合物と、 に）一般式 （式中Ｒ−Ｒ１／ｊ、水素原子又はアルキル基から選択
され２る同−又は異なる１価の原子又は基を表す。）で
示され るイミダゾール化合物とを必須出発成 分とする熱硬化性樹脂９５〜３０重量％と、 （［３） ポリビニルホルマール樹脂５〜７０重量％
と から成る耐熱接着剤用組成物。[Claims] (In the formula, R1d represents a hydrogen atom or an alkyl group, and R2 represents a divalent organic group 'r selected from -0-, -CH2-, -SO2-. , R3
represents a hydrogen atom or a rogen atom. ←) an aminophenol represented by the general formula (wherein R represents a monovalent atom or group selected from a hydrogen atom, a rogen atom, or an alkyl group); (c) an epoxy compound; 95 to 30% by weight of a thermosetting resin whose essential starting components are ([3) 5 to 70% by weight of a polyvinyl formal resin.
A composition for a heat-resistant adhesive consisting of.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15002082A JPS5941358A (en) | 1982-08-31 | 1982-08-31 | Composition for heat-resistant adhesive |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15002082A JPS5941358A (en) | 1982-08-31 | 1982-08-31 | Composition for heat-resistant adhesive |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5941358A true JPS5941358A (en) | 1984-03-07 |
Family
ID=15487729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15002082A Pending JPS5941358A (en) | 1982-08-31 | 1982-08-31 | Composition for heat-resistant adhesive |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5941358A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60210685A (en) * | 1984-04-05 | 1985-10-23 | Toshiba Chem Corp | Heat-resistant adhesive composition |
| WO2007142140A1 (en) * | 2006-06-06 | 2007-12-13 | Hitachi Chemical Company, Ltd. | Method for producing curing agent having acidic substituent and unsaturated maleimide group, thermosetting resin composition, prepreg, and laminate |
| JP2013157599A (en) * | 2012-01-04 | 2013-08-15 | Jnc Corp | Heat radiation member, electronic device, and battery |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56104979A (en) * | 1980-01-25 | 1981-08-21 | Hitachi Ltd | Thermosetting adhesive |
| JPS572328A (en) * | 1980-06-05 | 1982-01-07 | Toshiba Chem Corp | Composition for adhesive |
-
1982
- 1982-08-31 JP JP15002082A patent/JPS5941358A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56104979A (en) * | 1980-01-25 | 1981-08-21 | Hitachi Ltd | Thermosetting adhesive |
| JPS572328A (en) * | 1980-06-05 | 1982-01-07 | Toshiba Chem Corp | Composition for adhesive |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60210685A (en) * | 1984-04-05 | 1985-10-23 | Toshiba Chem Corp | Heat-resistant adhesive composition |
| WO2007142140A1 (en) * | 2006-06-06 | 2007-12-13 | Hitachi Chemical Company, Ltd. | Method for producing curing agent having acidic substituent and unsaturated maleimide group, thermosetting resin composition, prepreg, and laminate |
| US20120316263A1 (en) * | 2006-06-06 | 2012-12-13 | Shinji Tsuchikawa | Method for Producing Curing Agent Having Acidic Substituent and Unsaturated Maleimide Group, Thermosetting Resin Composition, Prepreg, and Laminate |
| US8461332B2 (en) | 2006-06-06 | 2013-06-11 | Hitachi Chemical Company, Ltd. | Method for producing curing agent having acidic substituent and unsaturated maleimide group, thermosetting resin composition, prepreg, and laminate |
| US8796473B2 (en) | 2006-06-06 | 2014-08-05 | Hitachi Chemical Company, Ltd. | Method for producing curing agent having acidic substituent and unsaturated maleimide group, thermosetting resin composition, prepreg, and laminate |
| JP2013157599A (en) * | 2012-01-04 | 2013-08-15 | Jnc Corp | Heat radiation member, electronic device, and battery |
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