JPH01167359A - Epoxy resin composition - Google Patents
Epoxy resin compositionInfo
- Publication number
- JPH01167359A JPH01167359A JP62325502A JP32550287A JPH01167359A JP H01167359 A JPH01167359 A JP H01167359A JP 62325502 A JP62325502 A JP 62325502A JP 32550287 A JP32550287 A JP 32550287A JP H01167359 A JPH01167359 A JP H01167359A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- type epoxy
- bisphenol
- resin composition
- anhydride
- 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
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 51
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 51
- 239000000203 mixture Substances 0.000 title claims abstract description 14
- 150000008065 acid anhydrides Chemical class 0.000 claims abstract description 13
- 230000003287 optical effect Effects 0.000 claims abstract description 8
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 claims abstract description 5
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000002156 mixing Methods 0.000 claims abstract description 4
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 7
- 238000007789 sealing Methods 0.000 claims description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract description 12
- 125000002723 alicyclic group Chemical group 0.000 abstract description 10
- 229930185605 Bisphenol Natural products 0.000 abstract description 9
- 239000006096 absorbing agent Substances 0.000 abstract description 6
- 239000003566 sealing material Substances 0.000 abstract 1
- 238000010521 absorption reaction Methods 0.000 description 11
- 239000012964 benzotriazole Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 5
- 239000012965 benzophenone Substances 0.000 description 5
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 5
- 239000011342 resin composition Substances 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- -1 diphenol compound Chemical class 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 2
- ZWAJLVLEBYIOTI-OLQVQODUSA-N (1s,6r)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCC[C@@H]2O[C@@H]21 ZWAJLVLEBYIOTI-OLQVQODUSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- PQJZHMCWDKOPQG-UHFFFAOYSA-N 2-anilino-2-oxoacetic acid Chemical compound OC(=O)C(=O)NC1=CC=CC=C1 PQJZHMCWDKOPQG-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 1
- GJEZBVHHZQAEDB-UHFFFAOYSA-N 6-oxabicyclo[3.1.0]hexane Chemical group C1CCC2OC21 GJEZBVHHZQAEDB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000004031 devitrification Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Led Device Packages (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は耐湿性と耐候性に優れた硬化物を与えるエポキ
シ樹脂組成物に関し、更に詳しくは直接屋外で使用され
る発光ダイオド−など光学素子を樹脂封止するためのエ
ポキシ樹脂組成物に関する。Detailed Description of the Invention [Field of Industrial Application] The present invention relates to an epoxy resin composition that provides a cured product with excellent moisture resistance and weather resistance. The present invention relates to an epoxy resin composition for resin-sealing.
近年、オプトエレクトロニクス関連技術の発展で光学素
子として各種発光素子、受光素子、光電変換素子、光フ
アイバー関連部品などに光透過性良好な透明エポキシ樹
脂が使用されている。特に発光素子としてＬＥＤは寿命
が長く低消費電力であり、いわゆるメンテナンスフリー
、省エネルギーである。従来ＬＥＤは屋外の標示用発光
素子としては揮度が不十分であったが、近時高揮度化が
進み、高揮度ＬＥＤとして５０００ミリｊ金ううになっ
た。In recent years, with the development of optoelectronics-related technology, transparent epoxy resins with good light transmittance have been used in various optical elements such as light emitting elements, light receiving elements, photoelectric conversion elements, optical fiber related parts, etc. In particular, LEDs as light emitting elements have a long lifespan, low power consumption, and are so-called maintenance-free and energy-saving. Conventionally, LEDs had insufficient volatility as light-emitting elements for outdoor markings, but recently the volatility has been increasing, and high-volatility LEDs have reached 5,000 millimeters of gold.
従来のエポキシ樹脂封止ＬＦＤをはじめ各種の発光素子
、受光素子は耐湿性と耐候性に関して信頼性が十分とは
いえなかった。このためＬＥＤや近接スイッチなど各種
の発光素子、受光素子を屋外で使用する場合には、これ
ら素子をガラス窓付きの金属ケースなどに収納し二重に
保護しなければならなかった。Various light emitting elements and light receiving elements including conventional epoxy resin-sealed LFDs have not been sufficiently reliable in terms of moisture resistance and weather resistance. For this reason, when various light emitting elements and light receiving elements such as LEDs and proximity switches are used outdoors, these elements must be double protected by being housed in a metal case with a glass window.
この様な状況を考慮して本発明者は屋外使用光学素子封
止材用エポキシ樹脂組成物を開発するために種々研究し
て、特定の樹脂の組合せの場合は耐湿性と耐候性が共に
良好となるとの知見を得、耐湿性と耐候性とが著しく優
れた屋外使用光学素子封止用樹脂組成物を見出し、本発
明を完成した。Taking these circumstances into consideration, the present inventor conducted various studies to develop an epoxy resin composition for encapsulant for optical elements used outdoors, and found that a specific combination of resins has good moisture resistance and weather resistance. Based on this knowledge, the inventors discovered a resin composition for sealing optical elements for outdoor use that has extremely excellent moisture resistance and weather resistance, and completed the present invention.
本発明は、ビスフェノール型エポキシ樹脂、脂環型エポ
キシ樹脂および酸無水物より成り、ビスフェノール型エ
ポキシ樹脂と脂環型エポキシ樹脂との混合比（重量比）
が８５：１５〜５ｏ：５０であり、更に紫外線吸収剤を
含有することを特徴とする屋外使用光学素子封止用エポ
キシ樹脂組成物である。The present invention consists of a bisphenol type epoxy resin, an alicyclic epoxy resin, and an acid anhydride, and the mixing ratio (weight ratio) of the bisphenol type epoxy resin and the alicyclic epoxy resin.
is 85:15 to 5o:50, and further contains an ultraviolet absorber.
本発明においてビスフェノール型エポキシ樹脂とは、フ
ェノール、クレゾール、キシレノールなどのモノフェノ
ールをホルムアルデヒド、アセトアルデヒド、アセトン
などのアルデヒド又はケトンと反応させてｊｑられる三
核体化したジフェノ−゛ル化合物（所謂ビスフェノール
化合物である）を更にグリシジルエーテル化したもので
ある。これらビスフェノール型エポキシ樹脂の中でビス
フェノールＡ型及びビスフェノールＦ型のエポキシ樹脂
が好ましい。脂環型エポキシ樹脂とは、シクロヘキザン
オキサイド、トリシクロデセンオキサイド、シクロペン
テンオキサイド構造を有するものである。これらの脂環
型エポキシ樹脂の中で３°、４°−エボキシーシクロヘ
キシルメチル−３，４−舎エボキシーシクロヘキ］ナン
カルボキシレート及び３°。In the present invention, bisphenol type epoxy resin refers to a trinuclear diphenol compound (so-called bisphenol compound) which is produced by reacting a monophenol such as phenol, cresol, or xylenol with an aldehyde or ketone such as formaldehyde, acetaldehyde, or acetone. ) is further glycidyl etherified. Among these bisphenol type epoxy resins, bisphenol A type and bisphenol F type epoxy resins are preferred. The alicyclic epoxy resin has a cyclohexane oxide, tricyclodecene oxide, or cyclopentene oxide structure. Among these alicyclic epoxy resins, 3°, 4°-epoxycyclohexylmethyl-3,4-aryl epoxycyclohexylnancarboxylate and 3°.
４゛−エポキシ８＝−６ニメチルーシクロヘキシルメチ
ルー
ンカル小キシレートが好ましい。Preferred is 4'-epoxy 8=-6 dimethyl-cyclohexylmethylone calxylate.
ビスフェノール型エポキシ樹脂及び脂環型エポキシ樹脂
は低粘度で、反応性、硬化物性に優れている。Bisphenol type epoxy resins and alicyclic type epoxy resins have low viscosity and are excellent in reactivity and curing properties.
ビスフェノール型エポキシ樹脂は吸湿処理において吸水
率は小さいが、樹脂硬化物に対し水分の相溶性が低いた
め、失透し透明性が低下する。又、芳香環を有するため
耐候性が十分でない。Bisphenol-type epoxy resins have a low water absorption rate during moisture absorption treatment, but their water compatibility with the cured resin product is low, resulting in devitrification and decreased transparency. Also, since it has an aromatic ring, it does not have sufficient weather resistance.
脂環型エポキシ樹脂は吸湿処理において、吸水率は大き
いが樹脂硬化物に対し水分の相溶性が高いため、透明性
が良好である。また、芳香環を含まないため耐候性、耐
光性にも優れている。In moisture absorption treatment, alicyclic epoxy resin has a high water absorption rate, but has high water compatibility with the cured resin product, so it has good transparency. Furthermore, since it does not contain aromatic rings, it has excellent weather resistance and light resistance.
ビスフェノール型エポキシ樹脂と脂環型エポキシ樹脂と
の混合比率は８５：１５〜５０ ： ５０（重量％）で
あり脂環型エポキシ樹脂が多い場合には耐湿処理におい
て吸湿率の増加が大きく、光学素子の耐湿性が低下する
。ビスフェノール型エポキシ樹脂が多い場合には吸湿処
理において失透し透明性の低下が大ぎく、更に耐候性、
耐光性の劣化も大きくなる。The mixing ratio of bisphenol type epoxy resin and alicyclic epoxy resin is 85:15 to 50:50 (wt%), and if there is a large amount of alicyclic epoxy resin, the moisture absorption rate will increase greatly in the moisture resistance treatment, and the optical element moisture resistance decreases. If there is a large amount of bisphenol-type epoxy resin, it will devitrify during moisture absorption treatment, resulting in a significant decrease in transparency, as well as poor weather resistance and
Deterioration of light resistance also increases.
エポキシ樹脂硬化剤としての酸無水物は、ヘキサヒドロ
フタル酸無水物、メチルヘキサヒドロフタル酸無水物、
テトラヒドロフタル酸無水物、メチルテトラヒドロフタ
ル酸無水物、メチルエンドメチレンテトラヒドロフタル
酸無水物、メチルエンドメチレンへキサヒドロフタル酸
無水物などの常温で液状か又は比較的融点の低い脂環型
酸無水物が好ましく用いられる。特にヘキサヒドロフタ
ル酸無水物及び／又はメチルヘキサヒドロフタル酸無水
物が良好である。これら酸無水物はシクロヘキサン環を
持つためにこれに基づく耐候性、変色安定性を発揮する
。Acid anhydrides as epoxy resin curing agents include hexahydrophthalic anhydride, methylhexahydrophthalic anhydride,
Alicyclic acid anhydrides that are liquid at room temperature or have a relatively low melting point, such as tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylendomethylenetetrahydrophthalic anhydride, and methylendomethylenehexahydrophthalic anhydride. is preferably used. Particularly good are hexahydrophthalic anhydride and/or methylhexahydrophthalic anhydride. Since these acid anhydrides have a cyclohexane ring, they exhibit weather resistance and discoloration stability based on this ring.
エポキシ樹脂と酸無水物との当量比はエポキシ樹脂に対
し０．９〜１．０が好ましい。当量比０。The equivalent ratio of the epoxy resin to the acid anhydride is preferably 0.9 to 1.0 relative to the epoxy resin. Equivalence ratio 0.
９以下では、硬化時の着色が著しく、本来の目的である
透明性に悪影響を及ぼす。また当量比１。If it is less than 9, coloration during curing is significant and the original objective of transparency is adversely affected. Also, the equivalence ratio is 1.
０以上の場合は吸水率が大ぎく耐湿性が低下する。If it is 0 or more, the water absorption rate is too large and the moisture resistance is reduced.
更にエポキシ樹脂及び酸無水物の他に硬化促進剤を添加
することが出来る。硬化促進剤として、などを用いるこ
とができる。硬化促進剤の添加量はエポキシ樹脂に対し
て通常０．１〜３％である。Furthermore, a curing accelerator can be added in addition to the epoxy resin and acid anhydride. As a curing accelerator, etc. can be used. The amount of curing accelerator added is usually 0.1 to 3% based on the epoxy resin.
エポキシ樹脂及び酸無水物の他に紫外線吸収剤を添加す
る。特に屋外使用光学素子の場合直射日光中に含まれる
短波長紫外光線による樹脂硬化物の劣化防止の必要があ
る。In addition to the epoxy resin and acid anhydride, a UV absorber is added. Particularly in the case of optical elements for outdoor use, it is necessary to prevent deterioration of cured resin products due to short wavelength ultraviolet rays contained in direct sunlight.
紫外線吸収剤としては、ベンゾフェノン系、ベンゾトリ
アゾール系、オキザリックアッシドアニリド系、Ｐ−ヒ
ドロキシベンゾエート系及びヒンダードアミン系等があ
げられるが、ベンゾフェノン系とベンゾトリアゾール系
の併用が特に良好である。Examples of the ultraviolet absorber include benzophenone, benzotriazole, oxalic acid anilide, P-hydroxybenzoate, hindered amine, etc., and combinations of benzophenone and benzotriazole are particularly suitable.
これらの紫外線吸収剤の例としては、ベンゾフェノン系
として、２−ヒドロキシ−４−メトキシベンゾフェノン
、２−ヒドロキシ−４−オクトキシベンゾフェノンなど
があり、ベンゾトリアゾール系として、２−（２°−ヒ
ドロキシ−３°、５°−を−アミルフェニル）−ベンゾ
トリアゾール、２−（２“−ヒドロキシ−３゛−ｔ−ブ
チル−５゛〜メチルフエニル）−５−クロロベンゾトノ
アゾール、２−（２゛−ヒドロキシ−３°、５°−ｔ−
ブチルフェニル）−ベンゾトリアゾール、２−（２”−
ヒドロキシ−５°−１−オクチルフェニルヒベンゾトリ
アゾールなどがある。Examples of these UV absorbers include 2-hydroxy-4-methoxybenzophenone and 2-hydroxy-4-octoxybenzophenone as benzophenone-based agents, and 2-(2°-hydroxy-3-hydroxybenzophenone) as benzotriazole-based agents. °, 5°-amylphenyl)-benzotriazole, 2-(2"-hydroxy-3'-t-butyl-5'-methylphenyl)-5-chlorobenzotonoazole, 2-(2'-hydroxy- 3°, 5°-t-
butylphenyl)-benzotriazole, 2-(2”-
Examples include hydroxy-5°-1-octylphenylhibenzotriazole.
好ましくはベンゾフェノン系紫外線吸収剤とベンゾトリ
アゾール系紫外線吸収剤と併用する。ベンゾフェノン系
紫外線吸収剤は３００ｎｍ以下の短波長領域に吸収のピ
ークがあり、ベンゾトリアゾール系紫外線吸収剤は３０
０止以上の長波長領域に吸収のピークを持つため、これ
らの組合せにより紫外線を広範囲に吸収する事ができる
ものである。紫外線吸収剤は粉末状であるが、エポキシ
樹脂及び酸無水物に対する溶解性、相溶性の良好なこと
、組成物との混合の際着色がないことが重要である。Preferably, a benzophenone ultraviolet absorber and a benzotriazole ultraviolet absorber are used together. Benzophenone UV absorbers have an absorption peak in the short wavelength region of 300 nm or less, and benzotriazole UV absorbers have an absorption peak of 300 nm or less.
Since it has an absorption peak in a long wavelength region of 0 or more, it is possible to absorb ultraviolet rays over a wide range by combining these. Although the ultraviolet absorber is in powder form, it is important that it has good solubility and compatibility with the epoxy resin and acid anhydride, and that it is not colored when mixed with the composition.
これら紫外線吸収剤の添加量はエポキシ樹脂に対してそ
れぞれ０．１〜２．０％である。本発明の樹脂組成物を
製造する方法はエポキシ樹脂に粉末状である紫外線吸収
剤を添加し、８０〜１２０℃で１０〜２０分間加熱攪拌
して溶解する。次いで６０℃以下の適当な温度まで樹脂
を冷却し、この中へ硬化剤成分を混合してエポキシ樹脂
組成物を得る。The amount of each of these ultraviolet absorbers added is 0.1 to 2.0% based on the epoxy resin. The method for producing the resin composition of the present invention is to add a powdered ultraviolet absorber to an epoxy resin, and dissolve it by heating and stirring at 80 to 120° C. for 10 to 20 minutes. Next, the resin is cooled to a suitable temperature of 60° C. or lower, and a curing agent component is mixed therein to obtain an epoxy resin composition.
耐湿性及び耐候性に優れており、屋外使用に適した光学
素子用エポキシ樹脂組成物が提供できる。An epoxy resin composition for optical elements that has excellent moisture resistance and weather resistance and is suitable for outdoor use can be provided.
以下実施例、比較例により本発明を更に詳しく説明する
。実施例、比較例中における「部」は重量部を意味する
。The present invention will be explained in more detail below using Examples and Comparative Examples. "Parts" in Examples and Comparative Examples mean parts by weight.
実施例１
ビスフェノールＦ型エポキシ樹脂
（油化シェルエポキシ■製エピコート８０７、エポキシ
当量１８６）
８５部
１５部
無水へキサヒドロフタル酸
（酸無水物当ｊｉｉ１５４） ９２部
２−ヒドロキシ−４−オクトキシベンゾフェノン０．３
部
２−（２−ヒドロキシ−３”、５’−ｔ−アミルフェニ
ル）−ベンゾトリアゾール
０、３部
酸化防止剤
小母
２−エチル−４メチルイミダゾール
０．３部
ｕ−ｃａｔＳＡ１０２
（サンアプロ製）
０．８部
上記化合物を１２０℃まで加温溶解混合し樹脂組成物を
得た。厚さ３Ｍの金型に注型して、１００℃２時間更に
１３０℃３時間硬化させ樹脂硬化物を得た。Example 1 Bisphenol F type epoxy resin (Epicote 807 manufactured by Yuka Shell Epoxy ■, epoxy equivalent 186) 85 parts 15 parts Hexahydrophthalic anhydride (acid anhydride equivalent JII 154) 92 parts 2-hydroxy-4-octoxybenzophenone 0.3
Part 2-(2-hydroxy-3'',5'-t-amylphenyl)-benzotriazole 0, 3 parts Antioxidant 2-ethyl-4-methylimidazole 0.3 parts u-catSA102 (manufactured by San-Apro) 0 .8 parts of the above compound were heated and mixed to 120°C to obtain a resin composition.It was cast into a mold with a thickness of 3M and cured at 100°C for 2 hours and further at 130°C for 3 hours to obtain a cured resin. .
実施例２〜４
実施例１と同様にして第１表の配合に従い樹脂組成物を
製造し、次いで樹脂硬化物を得た。Examples 2 to 4 Resin compositions were produced in the same manner as in Example 1 according to the formulations in Table 1, and then cured resin products were obtained.
比較例１〜４
実施例１と同様にして第１表の配合に従い樹脂組成物を
製造し、次いで樹脂硬化物を得た。Comparative Examples 1 to 4 Resin compositions were produced in the same manner as in Example 1 according to the formulations in Table 1, and then cured resin products were obtained.
耐湿性をみるための煮沸吸水試験方法は、ＪＩＳＫ−６
９１１に基づき実施し、吸水率により判定を行ない、ま
たその時の外観劣化状態を観察しＪＩＳＤ−０２０５＋
に基づき実施した。即ち、カーボンアークウェザ−メー
タ（降雨周期６０分、降雨時間１２分サイクル）を用い
て１０００時間の耐候試験を行ない、更に試験後の黄変
度を観察した。The boiling water absorption test method to check moisture resistance is JISK-6.
JISD-0205+
It was carried out based on the following. That is, a weather resistance test was conducted for 1000 hours using a carbon arc weather meter (60 minute rain cycle, 12 minute rain time cycle), and the degree of yellowing was further observed after the test.
その結果を第２表に示す。The results are shown in Table 2.
上記実施例、比較例により本発明のエポキシ樹脂組成物
は耐湿性及び耐候製に優れていることが明らかになった
。The above Examples and Comparative Examples reveal that the epoxy resin composition of the present invention has excellent moisture resistance and weather resistance.
Claims (2)
樹脂および酸無水物とより成り、ビスフェノール型エポ
キシ樹脂と脂環型エポキシ樹脂との混合比（重量比）が
８５：１５〜５０：５０であり、更に紫外線吸収剤を含
有することを特徴とする屋外使用光学素子封止用エポキ
シ樹脂組成物。(1) Consists of a bisphenol-type epoxy resin, an alicyclic-type epoxy resin, and an acid anhydride, and the mixing ratio (weight ratio) of the bisphenol-type epoxy resin and the alicyclic-type epoxy resin is 85:15 to 50:50, An epoxy resin composition for sealing an optical element for outdoor use, further comprising an ultraviolet absorber.
はメチルヘキサヒドロフタル酸無水物であり、エポキシ
樹脂と酸無水物との当量比が０．９〜１．０であること
を特徴とする特許請求の範囲第１項記載のエポキシ樹脂
組成物。(2) The acid anhydride is hexahydrophthalic anhydride and/or methylhexahydrophthalic anhydride, and the equivalent ratio of the epoxy resin and the acid anhydride is 0.9 to 1.0. An epoxy resin composition according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62325502A JPH01167359A (en) | 1987-12-24 | 1987-12-24 | Epoxy resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62325502A JPH01167359A (en) | 1987-12-24 | 1987-12-24 | Epoxy resin composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01167359A true JPH01167359A (en) | 1989-07-03 |
Family
ID=18177593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62325502A Pending JPH01167359A (en) | 1987-12-24 | 1987-12-24 | Epoxy resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01167359A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05208440A (en) * | 1991-07-30 | 1993-08-20 | Protechnic Sa | Method for producing heat adhesion item, device for executing the same and item obtained thereby |
| JP2001102639A (en) * | 1999-09-30 | 2001-04-13 | Sumitomo 3M Ltd | Light-emitting diode and laser diode device sealed with fluoropolymer |
| EP1187226A1 (en) * | 2000-09-01 | 2002-03-13 | Citizen Electronics Co., Ltd. | Surface-mount type light emitting diode and method of manufacturing same |
| JP2006070221A (en) * | 2004-09-06 | 2006-03-16 | Three Bond Co Ltd | Organic el element-sealing material |
| JP2006228708A (en) * | 2005-01-20 | 2006-08-31 | Mitsui Chemicals Inc | Organic el sealant |
| WO2010035502A1 (en) * | 2008-09-29 | 2010-04-01 | 三井化学株式会社 | Sealant, sealing member and organic el device |
| JP2015007146A (en) * | 2013-06-24 | 2015-01-15 | 日立化成株式会社 | Element sealing epoxy resin molding material and electronic part device |
| JP2017165980A (en) * | 2017-06-05 | 2017-09-21 | 日立化成株式会社 | Element sealing epoxy resin molding material and electronic component device |
| JP2020063366A (en) * | 2018-10-17 | 2020-04-23 | 日立化成株式会社 | Additive for curable resin composition, curable resin composition and electronic component device |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50139198A (en) * | 1974-04-11 | 1975-11-06 | ||
| JPS5483999A (en) * | 1977-12-16 | 1979-07-04 | Asahi Denka Kogyo Kk | Energy ray-curable epoxy resin composition |
| JPS59199713A (en) * | 1983-04-27 | 1984-11-12 | Sumitomo Bakelite Co Ltd | Adjustment of refractive index of cured epoxy resin |
| JPS6036565A (en) * | 1983-08-09 | 1985-02-25 | Asahi Glass Co Ltd | Curable resin composition |
| JPS6064483A (en) * | 1983-09-20 | 1985-04-13 | Toshiba Corp | Resin sealed light-emitting device |
| JPS60140884A (en) * | 1983-12-28 | 1985-07-25 | Nitto Electric Ind Co Ltd | Epoxy resin composite for optical semiconductor sealing |
-
1987
- 1987-12-24 JP JP62325502A patent/JPH01167359A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50139198A (en) * | 1974-04-11 | 1975-11-06 | ||
| JPS5483999A (en) * | 1977-12-16 | 1979-07-04 | Asahi Denka Kogyo Kk | Energy ray-curable epoxy resin composition |
| JPS59199713A (en) * | 1983-04-27 | 1984-11-12 | Sumitomo Bakelite Co Ltd | Adjustment of refractive index of cured epoxy resin |
| JPS6036565A (en) * | 1983-08-09 | 1985-02-25 | Asahi Glass Co Ltd | Curable resin composition |
| JPS6064483A (en) * | 1983-09-20 | 1985-04-13 | Toshiba Corp | Resin sealed light-emitting device |
| JPS60140884A (en) * | 1983-12-28 | 1985-07-25 | Nitto Electric Ind Co Ltd | Epoxy resin composite for optical semiconductor sealing |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05208440A (en) * | 1991-07-30 | 1993-08-20 | Protechnic Sa | Method for producing heat adhesion item, device for executing the same and item obtained thereby |
| JP2001102639A (en) * | 1999-09-30 | 2001-04-13 | Sumitomo 3M Ltd | Light-emitting diode and laser diode device sealed with fluoropolymer |
| EP1187226A1 (en) * | 2000-09-01 | 2002-03-13 | Citizen Electronics Co., Ltd. | Surface-mount type light emitting diode and method of manufacturing same |
| JP2006070221A (en) * | 2004-09-06 | 2006-03-16 | Three Bond Co Ltd | Organic el element-sealing material |
| JP2006228708A (en) * | 2005-01-20 | 2006-08-31 | Mitsui Chemicals Inc | Organic el sealant |
| WO2010035502A1 (en) * | 2008-09-29 | 2010-04-01 | 三井化学株式会社 | Sealant, sealing member and organic el device |
| JP5449176B2 (en) * | 2008-09-29 | 2014-03-19 | 三井化学株式会社 | Sealant, sealing member, and organic EL device |
| JP2015007146A (en) * | 2013-06-24 | 2015-01-15 | 日立化成株式会社 | Element sealing epoxy resin molding material and electronic part device |
| JP2017165980A (en) * | 2017-06-05 | 2017-09-21 | 日立化成株式会社 | Element sealing epoxy resin molding material and electronic component device |
| JP2020063366A (en) * | 2018-10-17 | 2020-04-23 | 日立化成株式会社 | Additive for curable resin composition, curable resin composition and electronic component device |
| WO2020080369A1 (en) * | 2018-10-17 | 2020-04-23 | 日立化成株式会社 | Additive for curable resin compositions, curable resin composition and electronic component device |
| CN112771122A (en) * | 2018-10-17 | 2021-05-07 | 昭和电工材料株式会社 | Additive for curable resin composition, and electronic component device |
| CN112771122B (en) * | 2018-10-17 | 2023-02-28 | 昭和电工材料株式会社 | Curable resin composition and electronic component device |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH01167359A (en) | Epoxy resin composition | |
| US3327016A (en) | Epoxide compositions cured with 1, 4-bis (aminomethyl) cyclohexane | |
| WO2001092396A1 (en) | Epoxy-resin systems, which are resistant to ageing, moulding materials and components produced therefrom and the use thereof | |
| JP3153171B2 (en) | Optical semiconductor device and epoxy resin composition for encapsulating optical semiconductor | |
| KR101597837B1 (en) | Epoxy resin composition for optical semiconductor light-receiving element encapsulation and process for producing the same, and optical semiconductor device | |
| JP5242530B2 (en) | Epoxy resin composition for optical semiconductor element sealing and optical semiconductor device | |
| JP4515009B2 (en) | Resin composition for sealing light emitting diode | |
| JP2002012743A (en) | Epoxy resin composition for sealing optical semiconductor, and optical semiconductor device sealed with its cured material | |
| JPH06128359A (en) | Epoxy resin composition and photosemiconductor device sealed therewith | |
| JP2807094B2 (en) | Epoxy resin composition for optical semiconductor encapsulation | |
| JP2724499B2 (en) | Epoxy resin composition | |
| JP3017888B2 (en) | Semiconductor device | |
| JP2992313B2 (en) | Epoxy resin composition | |
| JP2006111823A (en) | Epoxy resin composition for sealing optical semiconductor element and optical semiconductor by using the same | |
| JP2933771B2 (en) | Epoxy resin composition for optical semiconductor encapsulation | |
| JP2003064243A (en) | Epoxy resin composition for sealing optical semiconductor and optical semiconductor device | |
| JPS6079033A (en) | Epoxy resin composition suitable for element sealing | |
| JPH03201470A (en) | Optical semiconductor device | |
| JPS6131424A (en) | Epoxy resin composition giving transparent cured article | |
| JP2746905B2 (en) | Epoxy resin composition for optical semiconductor encapsulation | |
| JPS61159754A (en) | Resin sealed type semiconductor device | |
| JPH03208844A (en) | Artificial marble produced by using epoxy resin | |
| JP2001226450A (en) | Epoxy resin composition for sealing photosemiconductor and photosemiconductor device | |
| JPH06840B2 (en) | Epoxy resin composition for optical element | |
| JPH0827253A (en) | Photosemiconductor apparatus |