WO2012056629A1 - 樹脂組成物 - Google Patents
樹脂組成物 Download PDFInfo
- Publication number
- WO2012056629A1 WO2012056629A1 PCT/JP2011/005373 JP2011005373W WO2012056629A1 WO 2012056629 A1 WO2012056629 A1 WO 2012056629A1 JP 2011005373 W JP2011005373 W JP 2011005373W WO 2012056629 A1 WO2012056629 A1 WO 2012056629A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- resin
- mass
- resin composition
- parts
- epoxy
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
- C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
- C08L61/14—Modified phenol-aldehyde condensates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- 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
- C09J161/00—Adhesives based on condensation polymers of aldehydes or ketones; Adhesives based on derivatives of such polymers
- C09J161/04—Condensation polymers of aldehydes or ketones with phenols only
- C09J161/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
- C09J161/14—Modified phenol-aldehyde condensates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/66—Substances characterised by their function in the composition
Definitions
- the present invention relates to a resin composition having reduced elasticity, and more specifically, a resin having at least stress relaxation performance, compatibility, and adhesiveness, comprising at least a phenol resin having a dicyclopentadiene skeleton and a side chain epoxy-modified silicone resin. Relates to the composition.
- Silicone resin is a resin with excellent water repellency, electrical insulation, flexibility, and fluidity, but generally has poor compatibility with other resin materials, and is blended in order to obtain a uniform curing system. However, the adhesiveness is also poor.
- a first object of the present invention is to provide a resin composition that uses a silicone resin and is excellent in adhesion and insulation.
- the second object of the present invention is to provide an epoxy adhesive utilizing a silicone resin.
- the present inventors have obtained excellent and excellent compatibility between the phenol resin having a dicyclopentadiene skeleton and the side chain type epoxy-modified silicone resin.
- the present inventors have found that the resin composition is excellent in insulation and adhesiveness, and have reached the present invention.
- the present invention is based on (A) 100 parts by mass of a phenolic resin having a dicyclopentadiene skeleton, and (B) at least 33.3 to 800 parts by mass of a side chain type epoxy-modified silicone resin and (C) curing for epoxy resin.
- a resin composition characterized by containing 0.17 to 100 parts by mass of an agent, and an adhesive comprising the resin composition.
- the cured product of the resin composition of the present invention is improved in water repellency, electrical insulation, and flexibility, has good stress relaxation properties, and adheres firmly to a silicon wafer. Has characteristics.
- the present invention relates to (B) side chain type epoxy-modified silicone resin (33.3 to 800 parts by mass) and (C) a curing agent for epoxy resin with respect to (A) 100 parts by mass of phenol resin having a dicyclopentadiene skeleton. Since it is a resin composition characterized by containing 0.17 to 100 parts by mass and an adhesive comprising the resin composition, these components will be described in detail below.
- the amount of the phenol resin having a dicyclopentadiene skeleton needs to be 10 to 60% by mass in the resin composition, and is preferably 15 to 50% by mass. If it is less than 10% by mass, not only the adhesiveness but also the insulation performance is deteriorated. If it is used in excess of 60% by mass, the elastic modulus is increased and the stress relaxation performance is impaired.
- the side chain type epoxy-modified silicone resin of the component (B) used in the present invention is preferably a compound represented by the following general formula (II).
- the amount of the side chain type epoxy-modified silicone resin which is the component (B) in the present invention is 33.3 to 800 parts by mass with respect to 100 parts by mass of the phenol resin having a dicyclopentadiene skeleton as the component (A). It is necessary that the amount is 20 to 80% by mass in the resin composition, and preferably 25 to 75% by mass. If it is less than 20% by mass, the elastic modulus becomes high and the stress relaxation performance is impaired. If it is used in excess of 80% by mass, not only the adhesiveness is lowered but also the insulation performance is lowered, which is not preferable.
- the (C) component epoxy resin curing agent used in the present invention can be appropriately selected from known curing agents generally used for epoxy resins.
- the curing agent include alkylenediamines such as ethylenediamine, 1,2-diaminopropane, 1,3-diaminopropane, 1,3-diaminobutane, and 1,4-diaminobutane; diethylenetriamine, triethylenetriamine, tetra Polyalkylpolyamines such as ethylenepentamine; alicyclic polyamines such as 1,3-diaminomethylcyclohexane, 1,2-diaminocyclohexane, 1,4-diamino-3,6-diethylcyclohexane, isophoronediamine; Aromatic polyamines such as xylylenediamine, diaminodiphenylmethane, diaminodiphenylsulfone;
- Guanamines such as benzoguanamine and acetoguanamine; 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-isopropylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-phenylimidazole, 2-phenyl-4 -Imidazoles such as methylimidazole and 2-aminopropylimidazole; oxalic acid dihydrazide, malonic acid dihydrazide, succinic acid dihydrazide, glutaric acid dihydrazide, adipic acid dihydrazide, suberic acid dihydrazide, azelaic acid dihydrazide, sebacic acid dihydrazide, etc. Of dihydrazides;
- polyamines and glycidyl ethers such as phenyl glycidyl ether, butyl glycidyl ether, bisphenol A-diglycidyl ether, bisphenol F-diglycidyl ether, or various epoxy resins such as glycidyl esters of carboxylic acid are used in a conventional manner.
- a polyepoxy addition modification product produced by reacting with a carboxylic acid such as phthalic acid, isophthalic acid, dimer acid, etc.
- polyamines and aldehydes such as formaldehyde and phenols having at least one aldehyde-reactive site in the nucleus, such as phenol, cresol, xylenol, tert-butylphenol, and resorcin, are prepared by a conventional method.
- Curing agent such as Mannich-modified product is prepared by reacting Te may be used.
- latent curing agents such as dicyandiamide, acid anhydrides, and imidazoles can be used.
- a urea type curing agent is a curing agent having a urea bond in the molecular structure
- specific products include, for example, Adeka Hardener EH-5001P (urea structure-containing amine-based curing agent manufactured by ADEKA), U -CAT 3502T (aromatic dimethylurea compound manufactured by San Apro Co., Ltd.), U-CAT 3503N (aliphatic dimethylurea compound manufactured by San Apro Co., Ltd.), Dyhard UR 500 (aromatic dimethylurea compound manufactured by Degussa Japan Co., Ltd.), And Dyhard® UR® 300 (aromatic dimethylurea compound manufactured by Degussa Japan), Dyhard® UR® 200 (aromatic dimethylurea compound manufactured by Degussa Japan), and the like.
- the amount of the epoxy resin curing agent (C) used in the present invention is 0.17 to 100 parts by mass with respect to 100 parts by mass of the phenol resin having a dicyclopentadiene skeleton as the component (A). It is necessary to be 0.1 to 10% by mass in the product, and preferably 1 to 5% by mass. If it is less than 0.1% by mass, the curing is poor and physical properties such as adhesion cannot be obtained. Moreover, when it exceeds 10 mass%, since an adverse effect on the insulation performance due to the excess is concerned, it is not preferable.
- the resin composition of the present invention includes a curing catalyst; a reactive or non-reactive diluent (plastic) such as a curing catalyst; monoglycidyl ethers, dioctyl phthalate, dibutyl phthalate, benzyl alcohol, and coal tar.
- fibers such as glass fiber, carbon fiber; cellulose, silica sand, cement, kaolin, clay, aluminum hydroxide, bentonite, talc, silica, fine powder silica, titanium dioxide, carbon black, graphite, iron oxide, bitumen Materials, metal particles, fillers or pigments such as resin particles coated with metal; thickeners; thixotropic agents; flame retardants; antifoaming agents; rust preventives; colloidal silica, colloidal alumina, etc.
- Additives; etc. may be further added, and adhesive resins such as xylene resin and petroleum resin are used as component (D) It can also be used in combination with.
- a silica filler in combination because not only the thermal linear expansion coefficient of the composition can be easily controlled, but also the elastic modulus can be improved and the strength can be increased.
- the component (D) used in the present invention can be used in various combinations, the total amount used is 100 parts by mass of a phenol resin having a dicyclopentadiene skeleton as the component (A) from the viewpoint of use as an adhesive. It is preferable that it is 699 mass parts or less with respect to 69.9 mass% in a resin composition.
- Epoxy-modified silicone resin [Compound wherein R 1 is —C 3 H 6 —, s is 200, and t is 80 in the general formula (II)]
- the compatibility was confirmed by mixing 100 parts by mass of the indicated amount of phenol resin. Evaluation criteria were evaluated in the following three stages. ⁇ : No turbidity ⁇ : Turbidity ⁇ : Separation (emulsification)
- the prepared adhesive was applied to a silicon wafer, preheated (130 ° C. ⁇ 10 minutes), and then fully cured (180 ° C. ⁇ 60 minutes).
- a peel test with an adhesive tape based on the cross-cut test method of JIS D0202 was performed to measure the number of remaining masses, and the adhesiveness was evaluated.
- the test piece cured on the silicon wafer was processed by being put under HAST conditions (130 ° C., 85% RH) for 24 hours, and the adhesive strength after the processing was measured by a cross-cut test method. It was evaluated with.
- the resin composition of the present invention comprising a phenol resin having a dicyclopentadiene skeleton and a side chain type epoxy-modified silicone resin is excellent not only in adhesiveness but also in interlayer insulation. It was confirmed to be a thing.
- the resin composition of the present invention is a resin composition having good adhesion to a silicon wafer.
- the composition itself is suitable for functioning as an interlayer insulating film or a protective film, it is extremely useful industrially.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Silicon Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
本発明の第2の目的は、シリコーン樹脂を利用したエポキシ系接着剤を提供することにある。
一般式(II):
但し、上式中のR1は炭素原子数1~10のアルキレン基を表し、sは10~300の整数、tは1~100の整数を表す。
本発明においては、特に、シリカフィラーを併用することが、組成物の熱線膨張係数の制御が容易となるだけでなく、弾性率を向上させて高強度とすることができるので好ましい。本発明で使用する(D)成分は種々組み合わせて使用することもできるが、その全使用量は、接着剤として使用する上から、(A)成分のジシクロペンタジエン骨格を有するフェノール樹脂100質量部に対して699質量部以下であり、樹脂組成物中の69.9質量%未満であることが好ましい。
以下、実施例によって本発明の樹脂組成物を更に詳細に説明するが、本発明はこれらによって限定されるものではない。
-C3H6-、sが200、tが80である化合物〕100質量部に対して、下記〔表1〕に示した量のフェノール樹脂100質量部を混合して相溶性を確認した。評価基準は、下記の三段階で評価した。
○:濁りなし
△:濁りあり
×:分離(乳化)
作製した接着剤をシリコンウエハに塗布し、予備加熱(130℃×10分)した後、本硬化(180℃×60分)させた。JIS D0202の碁盤目試験方法に準拠した、粘着テープによるピールテストを行って残マス数を計測し、接着性の評価を行った。更に、耐湿テスト後の評価として、前記シリコンウエハ上で硬化させた試験片をHAST条件下(130℃、85%RH)に24時間投入して処理し、処理後の接着力を碁盤目試験方法で評価した。
電解銅箔のマット面に接着剤を塗布し、130℃で10分間予備加熱した後、真空ラミネーターを用いて基板にラミネートし、次いで、180℃で60分間加熱して本硬化させた。銅箔の一部を電極として残し、残りをエッチングによって除去し、評価サンプルを得た。得られたサンプルについて、接着剤の層間絶縁性をHAST条件下(130℃、85%RH、バイアス:3.3V)で、評価した。
PETフィルム上に接着剤を塗布し、予備加熱(130℃で10分間)した後、本硬化(180℃で60分間)させた。PETフィルムから硬化物シートを剥がして、試験片を得た。動的粘弾性装置にて、-100℃~200℃の温度範囲で測定し、硬化物の弾性率を評価した。
Claims (6)
- (A)ジシクロペンタジエン骨格を有するフェノール樹脂100質量部に対して、少なくとも、(B)側鎖型エポキシ変性シリコーン樹脂33.3~800質量部及び(C)エポキシ樹脂用硬化剤0.17~100質量部を含有することを特徴とする樹脂組成物。
- 更に(D)成分として、硬化触媒、反応性又は非反応性の希釈剤(可塑剤)、繊維類、充填剤(フィラー)、顔料、増粘剤、チキソトロピック剤、難燃剤、消泡剤、防錆剤、及び粘着性の樹脂類からなる群の中から選択された少なくとも1種を含有する、請求項1~3の何れかに記載された樹脂組成物。
- 前記(D)成分の含有量が69.9質量%未満である、請求項1~4の何れかに記載された樹脂組成物。
- 請求項1~5に記載された何れかの樹脂組成物からなることを特徴とする接着剤。
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020137009131A KR20130141482A (ko) | 2010-10-26 | 2011-09-26 | 수지 조성물 |
CN201180050297.7A CN103168059B (zh) | 2010-10-26 | 2011-09-26 | 树脂组合物 |
JP2012540658A JP5881609B2 (ja) | 2010-10-26 | 2011-09-26 | 樹脂組成物 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2010239408 | 2010-10-26 | ||
JP2010-239408 | 2010-10-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2012056629A1 true WO2012056629A1 (ja) | 2012-05-03 |
Family
ID=45993377
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2011/005373 WO2012056629A1 (ja) | 2010-10-26 | 2011-09-26 | 樹脂組成物 |
Country Status (5)
Country | Link |
---|---|
JP (1) | JP5881609B2 (ja) |
KR (1) | KR20130141482A (ja) |
CN (1) | CN103168059B (ja) |
TW (1) | TW201219454A (ja) |
WO (1) | WO2012056629A1 (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104785707B (zh) * | 2015-04-17 | 2017-05-24 | 广西藤县通轩立信化学有限公司 | 铸造用酚醛树脂 |
TWI642746B (zh) * | 2017-07-27 | 2018-12-01 | 武漢市三選科技有限公司 | 底部塡充膠組成物及使用其之底部塡充方法與電子組裝元件 |
TWI775611B (zh) * | 2020-09-28 | 2022-08-21 | 上緯興業股份有限公司 | 有機矽改性的雙環戊二烯衍生之羥基芳香族化合物、其製備方法以及固化物 |
CN112646322B (zh) * | 2020-12-21 | 2023-06-23 | 上海中化科技有限公司 | 树脂组合物、树脂材料及其制备方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04363316A (ja) * | 1991-03-29 | 1992-12-16 | Matsushita Electric Works Ltd | エポキシ樹脂組成物 |
JPH06228275A (ja) * | 1993-02-08 | 1994-08-16 | Sumitomo Bakelite Co Ltd | エポキシ樹脂組成物 |
JPH10223660A (ja) * | 1997-01-31 | 1998-08-21 | Toshiba Chem Corp | 化合物半導体装置 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH06220160A (ja) * | 1993-01-27 | 1994-08-09 | Matsushita Electric Works Ltd | エポキシ樹脂組成物 |
KR100570725B1 (ko) * | 2001-09-28 | 2006-04-12 | 니폰 세키유 가가쿠 가부시키가이샤 | 페놀 수지, 에폭시 수지, 이들의 제조방법 및 에폭시 수지조성물 |
-
2011
- 2011-09-26 WO PCT/JP2011/005373 patent/WO2012056629A1/ja active Application Filing
- 2011-09-26 CN CN201180050297.7A patent/CN103168059B/zh not_active Expired - Fee Related
- 2011-09-26 KR KR1020137009131A patent/KR20130141482A/ko not_active Application Discontinuation
- 2011-09-26 JP JP2012540658A patent/JP5881609B2/ja active Active
- 2011-10-07 TW TW100136554A patent/TW201219454A/zh unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH04363316A (ja) * | 1991-03-29 | 1992-12-16 | Matsushita Electric Works Ltd | エポキシ樹脂組成物 |
JPH06228275A (ja) * | 1993-02-08 | 1994-08-16 | Sumitomo Bakelite Co Ltd | エポキシ樹脂組成物 |
JPH10223660A (ja) * | 1997-01-31 | 1998-08-21 | Toshiba Chem Corp | 化合物半導体装置 |
Also Published As
Publication number | Publication date |
---|---|
KR20130141482A (ko) | 2013-12-26 |
CN103168059A (zh) | 2013-06-19 |
TW201219454A (en) | 2012-05-16 |
JP5881609B2 (ja) | 2016-03-09 |
CN103168059B (zh) | 2016-01-13 |
JPWO2012056629A1 (ja) | 2014-03-20 |
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