KR100430626B1 - Thermofusion epoxy film having rapid curability and excellent storage stability at room temperature and method for manufacturing the same - Google Patents
Thermofusion epoxy film having rapid curability and excellent storage stability at room temperature and method for manufacturing the same Download PDFInfo
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- KR100430626B1 KR100430626B1 KR1019970001493A KR19970001493A KR100430626B1 KR 100430626 B1 KR100430626 B1 KR 100430626B1 KR 1019970001493 A KR1019970001493 A KR 1019970001493A KR 19970001493 A KR19970001493 A KR 19970001493A KR 100430626 B1 KR100430626 B1 KR 100430626B1
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- 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
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
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- 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
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/36—Layered products comprising a layer of synthetic resin comprising polyesters
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- 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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
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- 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
- B32B2255/00—Coating on the layer surface
- B32B2255/10—Coating on the layer surface on synthetic resin layer or on natural or synthetic rubber layer
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- 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
- B32B2255/00—Coating on the layer surface
- B32B2255/26—Polymeric coating
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Abstract
Description
본 발명은 열융착 에폭시 필름 및 그의 제조방법에 관한 것이다.The present invention relates to a heat-sealed epoxy film and a method for producing the same.
반도체 봉지, 구조용 접착제 및 실링 (Sealing) 제 등으로 사용되고 있는 열융착 에폭시 필름은 지금까지 경화성을 향상시키기 위해서 경화속도가 빠른 경화제 및 경화촉진제를 사용하여 왔으나, 이 경우 상온 방치시의 보관안정성이 나빠서 5℃ 이하의 저온에서 보관 및 수송을 해야하는 문제점이 있었다. 그 결과 보관 및 수송에 따른 비용이 상승하고 작업성이 저하되었다.Heat-sealed epoxy films used in semiconductor encapsulation, structural adhesives, and sealing agents have been used in the past to improve the curing properties, but the curing agent and the curing accelerator have a high curing rate. In this case, the storage stability at room temperature is poor. There was a problem in that the storage and transport at a low temperature below 5 ℃. As a result, the cost of storage and transportation has increased and workability has been reduced.
한편 열융착 에폭시 필름 제조시 상온에서의 보관안정성을 개선하기 위해서 경화속도가 느린 경화제를 사용하는 방법도 제시되고 있으나, 이와 같은 방법은 작업 시간이 길어져 작업 효율성이 저하되는 문제가 있다.Meanwhile, a method of using a curing agent having a low curing speed has been proposed to improve storage stability at room temperature when manufacturing a heat-sealed epoxy film. However, such a method has a problem in that working time decreases due to a long working time.
이상에서 설명한 문제들로 인하여 경화속도가 빠르면서도 상온에서의 보관안정성이 뛰어난 열융착 에폭시 필름의 개발에 대한 연구가 활발하게 진행되고 있으나 아직까지 만족할 만한 연구결과가 발표되고 있지 못한 실정이다.Due to the problems described above, research on the development of a heat-sealing epoxy film having a high curing rate and excellent storage stability at room temperature has been actively conducted, but satisfactory results have not been published.
본 발명은 보관안정성이 우수함과 동시에 경화속도가 빨라서 작업효율성이 향상되고, 보관 및 제조원가가 절감될 수 있는 열융착 에폭시 필름을 제공하고자 한다.The present invention is to provide a heat-sealed epoxy film that can be excellent in storage stability and at the same time the curing speed is improved work efficiency, storage and manufacturing cost can be reduced.
제 1 도 및 제 2 도는 본 발명의 열융착 에폭시 필름의 단면도이다.1 and 2 are cross-sectional views of the heat-sealed epoxy film of the present invention.
제 1 도 및 제 2 도에 있어서, 1은 폴리에스테르 필름이고, 2는 실리콘으로 이형처리된 폴리에스테르 필름층이고, 3은 에폭시 접착제 필름층이다.1 and 2, 1 is a polyester film, 2 is a polyester film layer release-treated with silicone, and 3 is an epoxy adhesive film layer.
본 발명은 경화속도가 빠르고 보관안정성이 우수한 열융착 에폭시 필름 및 그의 제조방법에 관한 것이다.The present invention relates to a heat-sealed epoxy film and a method for producing the same, the curing speed is excellent and the storage stability.
더욱 구체적으로 본 발명은 실리콘 수지로 이형처리된 폴리에스테르 필름 (1) 상에 이미다졸 화합물과 에폭시 화합물의 반응생성물을 열가소성 수지로 마이크로 캡슐화시킨 경화제를 10~50 중량% 함유하는 에폭시 접착제 필름 (3) 이 적층된 열융착 에폭시 필름에 관한 것이다.More specifically, the present invention relates to an epoxy adhesive film containing 10 to 50% by weight of a curing agent obtained by microencapsulating a reaction product of an imidazole compound and an epoxy compound with a thermoplastic resin on a
또한 본 발명은 실리콘 수지로 이형처리된 폴리에스테르 필름 (1) 상에 이미다졸 화합물과 에폭시 화합물의 반응생성물을 열가소성 수지로 마이크로 캡슐화시킨 경화제를 10∼50 중량% 함유하는 에폭시 접착제 필름 (3)용 용액을 필름상으로 코팅함을 특징으로 하는 열융착 에폭시 필름의 제조방법에 관한 것이다.In addition, the present invention is for epoxy adhesive film (3) containing 10 to 50% by weight of a curing agent in which the reaction product of the imidazole compound and the epoxy compound is microencapsulated with a thermoplastic resin on the polyester film (1) release-treated with a silicone resin. It relates to a method for producing a heat-sealed epoxy film characterized in that the solution is coated on a film.
본 발명에 사용된 에폭시 필름의 경화제는 이미다졸 화합물과 에폭시 화합물의 반응 생성물을 열가소성 수지로 마이크로 캡슐화시킨 것으로서 상온에서의 보관안정성이 우수하며, 경화속도가 빨라서 이상에서 설명한 문제점을 개선할 수 있다.여기에 사용된 이미다졸 화합물은 이미다졸, 2-메틸이미다졸, 2-에틸이미다졸, 2-에틸-4-메틸이미다졸, 2-페닐이미다졸, 1-시아노에틸-2-메틸이미다졸 및/또는 1-시아노에틸-2-에틸-4-메틸이미다졸 등이 사용되어진다. 이 이미다졸 화합물과 반응하여 이미다졸유도체 에폭시 화합물을 생성하는 에폭시 화합물로서는 비스페놀 A형 에폭시 수지, 페놀노블락 에폭시 수지, 비스페놀 F형 에폭시 수지 및 블락화비스페놀 A형 에폭시 수지 등의 글리시딜에테르형 에폭시 수지가 사용된다.The curing agent of the epoxy film used in the present invention is a microencapsulated reaction product of the imidazole compound and the epoxy compound with a thermoplastic resin, and has excellent storage stability at room temperature, and can improve the problems described above due to the fast curing speed. The imidazole compound used herein is imidazole, 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 1-cyanoethyl-2 -Methylimidazole and / or 1-cyanoethyl-2-ethyl-4-methylimidazole and the like are used. As an epoxy compound which reacts with this imidazole compound and produces | generates an imidazole derivative epoxy compound, glycidyl-ether epoxy, such as a bisphenol-A epoxy resin, a phenol noblock epoxy resin, a bisphenol F-type epoxy resin, and a bisphenol F-type epoxy resin Resin is used.
또한 이상에서 생성된 이미다졸유도체 에폭시 화합물을 캡슐화시키는 열가소성 수지로서는 폴리스티렌, 젤라틴 및 폴리이소시아네이트 등의 고분자가 사용된다.As the thermoplastic resin encapsulating the imidazole derivative epoxy compound produced above, a polymer such as polystyrene, gelatin and polyisocyanate is used.
이상에서 설명한 바와 같이 이미다졸 화합물과 에폭시 화합물의 반응 생성물을 열가소성 수지로 캡슐화시켜 만든 잠재성경화제를 본 발명의 에폭시 접착제 필름의 경화제로 에폭시 접착제 필름용 용액 전체 무게 대비 10∼50 중량% 범위내에서 사용한다. 10 중량% 미만으로 첨가하였을 경우는 기존 제품의 경화속도 보다는 빠른 경화거동을 보이나 130℃에서 2분 내에 경화가 되지 않으며, 50 중량%를 초과하는 경우에는 경화반응시 발생하는 열량이 너무 높아 접착제의 접착력이 오히려 저하된다.As described above, the latent curing agent formed by encapsulating the reaction product of the imidazole compound and the epoxy compound with a thermoplastic resin is within the range of 10 to 50% by weight based on the total weight of the solution for the epoxy adhesive film as the curing agent of the epoxy adhesive film of the present invention. use. When added in less than 10% by weight, the curing behavior is faster than that of the existing products, but it does not cure within 2 minutes at 130 ℃. If it exceeds 50% by weight, the amount of heat generated during the curing reaction is too high. Adhesion is rather lowered.
본 발명을 도면을 통하여 보다 상세하게 설명한다. 제 1 도 및 제 2 도는 본 발명의 열융착 에폭시 필름의 단면도를 나타낸다.The present invention will be described in more detail with reference to the drawings. 1 and 2 show cross-sectional views of the heat-sealed epoxy film of the present invention.
본 발명은 실리콘으로 이형처리된 폴리에스테르 필름층 (2) 상에 상기 경화제를 함유하는 에폭시 접착제 필름층 (3)을 적층한 것이다.This invention laminates | stacks the epoxy
에폭시 접착제 필름층을 구성하는 에폭시 수지는 한 분자내에 최소한 2개 이상의 에폭시반응기를 함유하고 있는 에폭시 수지이다. 예로, 비스페놀 A형 에폭시 수지, 비스페놀 F형 에폭시 수지, 비스페놀 S형 에폭시 수지, 페놀노블락형 에폭시 수지, 크레졸블락형 에폭시 수지, 다이머산(Dimer Acid) 변성 에폭시 수지, 고무변성 에폭시 수지, 우레탄변성 에폭시 수지, 페녹시 수지 및 폴리올변성 에폭시 수지 등이 사용되어진다. 이상에서 언급한 에폭시 수지들은 단독 또는 2종 이상을 혼합하여 사용하는 것이 일반적이나 본 발명에서는 잠재성경화제 등과의 배합성 및 상용성이 우수한 비스페놀 A형 에폭시 수지를 주성분으로 하고 기타 에폭시 수지들을 보조성분으로 혼합 사용한다.The epoxy resin constituting the epoxy adhesive film layer is an epoxy resin containing at least two epoxy reactors in one molecule. For example, bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, phenol noblock type epoxy resin, cresol block type epoxy resin, dimer acid modified epoxy resin, rubber modified epoxy resin, urethane modified epoxy Resins, phenoxy resins, polyol modified epoxy resins and the like are used. The epoxy resins mentioned above are generally used alone or in combination of two or more thereof. However, in the present invention, a bisphenol A type epoxy resin having excellent blendability and compatibility with a latent curing agent or the like is used as a main component, and other epoxy resins are auxiliary components. Use it as a mix.
또한 에폭시 접착제 필름층을 형성하기 위한 용제로서는 상기에 언급한 에폭시 수지를 완전히 용해시키는 용제로서 아세톤, 메틸에틸케톤, 메틸이소부틸케톤, 벤젠, 톨루엔, 크실렌, 메틸알콜, 에틸알콜, 이소프로필알콜 및 n-부틸알콜을 단독 또는 2종 이상 혼합하여 사용한다.In addition, the solvent for forming the epoxy adhesive film layer is a solvent for completely dissolving the above-mentioned epoxy resin as acetone, methyl ethyl ketone, methyl isobutyl ketone, benzene, toluene, xylene, methyl alcohol, ethyl alcohol, isopropyl alcohol and n-butyl alcohol is used individually or in mixture of 2 or more types.
제 1 도 및 제 2 도의 폴리에스테르 필름 (1) 의 두께는 25∼200㎛ 또는 12∼50㎛ 인 것이 바람직하다.It is preferable that the thickness of the
또한 폴리에스테르 필름 (1) 의 이형처리에 사용된 이형처리제의 경우는 열경화형 실리콘 수지로서, 디메틸폴리실록산을 중심으로 말단 및 측쇄의 일부 또는 전부에 비닐기, 수산기 및 페닐 등을 함유하며, 백금 등의 촉매를 이용하여 경화반응시킨 실리콘 수지가 사용되어진다. 실리콘 수지의 용제로서는 톨루엔, 크실렌, 메틸에틸케톤 및 n-헥산 등의 유기용제가 사용되며, 이들 유기용제에 실리콘 수지를 용해 또는 분산시켜 용액을 제조하며 그 농도는 0.5∼5.0 중량%의 범위가 적당하다.In the case of the release treatment agent used for the release treatment of the polyester film (1), as a thermosetting silicone resin, vinyl groups, hydroxyl groups, phenyl and the like are contained in part or all of the terminal and side chains, mainly dimethylpolysiloxane, and platinum, etc. The silicone resin hardened and reacted using the catalyst of is used. As the solvent of the silicone resin, organic solvents such as toluene, xylene, methyl ethyl ketone, and n-hexane are used, and a solution is prepared by dissolving or dispersing the silicone resin in these organic solvents, and the concentration is in the range of 0.5 to 5.0% by weight. It is suitable.
이상과 같이 조액을 한후, 이형처리된 폴리에스테르 필름상에 에폭시 접착제 필름용 용액을 나이프코터 (Knife Coater), 콤마코터 (Comma Coater), 에어나이프코터 (Air Knife Coater) 및 독타브레이드 (Docter Blade)를 이용하여 10∼1000㎛ 의 두께로 코팅한 후 건조하여 권취하고, 제품규격에 맞추어 슬리팅 (Slitting)하여 본 발명의 열융착 에폭시 필름을 제조한다.After the crude liquid is prepared as described above, the solution for epoxy adhesive film is coated on a release-treated polyester film with a knife coater, a comma coater, an air knife coater, and a doctor blade. After coating to a thickness of 10 ~ 1000㎛ using to dry and wound, and slitting (slitting) in accordance with the product specifications to prepare a heat-sealed epoxy film of the present invention.
이하 실시예 및 비교실시예를 통하여 본 발명을 보다 구체적으로 설명한다. 그러나 본 발명이 실시예에만 한정되는 것은 아니다.Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples. However, the present invention is not limited only to the examples.
실시예 1 ∼ 실시예 4 및 비교실시예 1 ~ 비교실시예 4Examples 1 to 4 and Comparative Examples 1 to 4
표 1 의 조성비에 따라서 고상인 비스페놀 A형 에폭시 수지, 페녹시 수지 및/또는 고무변성 에폭시 수지를 80℃인 톨루엔과 메틸에틸케톤의 혼합용제(톨루엔 : 메틸에틸케톤 = 3 : 1)에 용해시킨 후 계속 교반하면서 액체상태인 저분자량의 비스페놀 A형 에폭시 수지, 비스페놀 F형 에폭시 수지 및/또는 노블락 수지를 첨가하고, 여기에 이미다졸 화합물인 2-메틸이미다졸과 비스페놀 F형 에폭시 수지의 반응생성물을 열가소성 수지인 폴리스티렌으로 마이크로 캡슐화 시킨 경화제 (이하 마이크로 캡슐화 경화제라고 한다), 2-메틸이미다졸 단독 경화제 또는 2-에틸-4-메틸이미다졸 단독 경화제를 첨가하여 에폭시 접착제 필름용 용액을 제조한다.According to the composition ratio of Table 1, the solid bisphenol-A epoxy resin, phenoxy resin and / or rubber-modified epoxy resin were dissolved in a mixed solvent of toluene and methyl ethyl ketone at 80 ° C. (toluene: methyl ethyl ketone = 3: 1). After continuing stirring, a low molecular weight bisphenol A epoxy resin, a bisphenol F epoxy resin and / or a noblock resin in a liquid state were added thereto, and the reaction of the imidazole compound 2-methylimidazole and the bisphenol F epoxy resin was added thereto. The solution for the epoxy adhesive film was added by adding a curing agent (hereinafter referred to as a microencapsulating curing agent), a 2-methylimidazole homocuring agent, or a 2-ethyl-4-methylimidazole homocuring agent which microencapsulated the product into a polystyrene thermoplastic resin. Manufacture.
제조한 이들 용액을 이형처리된 폴리에스테르 필름 상에 독타브레이드로 50 ㎛의 두께로 코팅한 후 80℃의 열풍순환건조기 내에서 3분 동안 건조하여 각각 열융착 에폭시 필름을 제조한다.These prepared solutions were coated on a release-treated polyester film with a thickness of 50 μm with a dotablade and then dried in a hot air circulation dryer at 80 ° C. for 3 minutes to prepare a heat-sealed epoxy film.
제조한 열융착 에폭시 필름들의 물성을 평가한 결과는 표 2 와 같다.The results of evaluating the physical properties of the prepared heat-sealed epoxy films are shown in Table 2.
< 표 1 > 에폭시 접착제 필름용 용액 조성비<Table 1> Solution composition ratio for epoxy adhesive film
표 1 에서 마이크로 캡슐화 경화제는 2-메틸이미다졸과 비스페놀 F형 에폭시 수지의 반응생성물을 열가소성 수지인 폴리스티렌으로 마이크로 캡슐화시킨 경화제이다.In Table 1, the microencapsulation curing agent is a curing agent in which the reaction product of 2-methylimidazole and bisphenol F-type epoxy resin is microencapsulated with polystyrene which is a thermoplastic resin.
< 표 2 > 열융착 에폭시 필름의 물성<Table 2> Physical Properties of Thermal Fusion Epoxy Films
본 발명의 열융착 에폭시 필름은 이미다졸 화합물과 에폭시 화합물의 반응생성물을 열가소성 수지로 마이크로 캡슐화시킨 경화제를 사용하므로서 경화속도가 빠르고 상온 보관안정성이 우수하다. 그 결과 작업효율성이 향상되고, 보관 및 수송이 용이하여 제조원가가 절감된다.The heat-sealed epoxy film of the present invention uses a curing agent obtained by microencapsulating a reaction product of an imidazole compound and an epoxy compound with a thermoplastic resin, and thus has a high curing rate and excellent room temperature storage stability. As a result, work efficiency is improved, and storage and transportation are easy, thereby reducing manufacturing costs.
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| KR1019970001493A KR100430626B1 (en) | 1997-01-20 | 1997-01-20 | Thermofusion epoxy film having rapid curability and excellent storage stability at room temperature and method for manufacturing the same |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07173448A (en) * | 1993-12-17 | 1995-07-11 | Sumitomo Bakelite Co Ltd | Anisotropically conductive film |
| KR950032394A (en) * | 1994-03-15 | 1995-12-20 | 마에다 카쯔노수케 | Microcapsule Type Hardener, Preparation Method, Thermosetting Resin Composition, Prepreg and Fiber Reinforced Composite |
| JPH08185713A (en) * | 1994-12-28 | 1996-07-16 | Sumitomo Bakelite Co Ltd | Anisotropic conductive film |
| JPH08295854A (en) * | 1995-04-25 | 1996-11-12 | Sony Chem Corp | Adhesive film having anisotropic electrocondutivity |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07173448A (en) * | 1993-12-17 | 1995-07-11 | Sumitomo Bakelite Co Ltd | Anisotropically conductive film |
| KR950032394A (en) * | 1994-03-15 | 1995-12-20 | 마에다 카쯔노수케 | Microcapsule Type Hardener, Preparation Method, Thermosetting Resin Composition, Prepreg and Fiber Reinforced Composite |
| JPH08185713A (en) * | 1994-12-28 | 1996-07-16 | Sumitomo Bakelite Co Ltd | Anisotropic conductive film |
| JPH08295854A (en) * | 1995-04-25 | 1996-11-12 | Sony Chem Corp | Adhesive film having anisotropic electrocondutivity |
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