201141899 . 六、發明說明： 【發明所屬之技術領域】 » 本發明係關於低黏度、有機氯量少、耐熱性高、調配 二故甲基丙燒之環氧丙基趟（Trimethyl〇lpr〇pane glycidyl ether)以作為必須成分之樹脂組成物以及其硬 化物，其係適合使用在以半導體密封材用途為首之電氣絕 緣材料之等電氣/電子產業。 【先前技術】 %氧樹脂係有著由液狀以至固形之各式型態者，且因 環氧樹脂與硬化劑之反應性優異而易於處理，當藉由硬化 劑使其交聯時，係成為具有大的交聯密度之硬化樹脂，其 係表現出優異的财熱性、财濕性、财藥品性、電特性等， 而多被用於電氣/電子領域。 環氧樹脂係正被廣泛使用於工業用途，惟近年來其要 求的性能正逐漸高度化。例如，以環氧樹脂作為主劑的樹 脂組成物所代表的領域的半導體密封材料，惟近年來隨著 半導體元件的積體度提升’封裝件（Package )尺寸趨於大面 積化、薄型化的同時’安裝方式亦朝表面安裝化的方面進 展，而期望開發出融焊耐熱性更為優良的材料。 此外，以近來高積體化、高密度安裝化之動向而言， 正由以往之利用模具轉注（Transfer)成形之封裝件，改變 為併合積體電路（Hybrid 1C)、板上晶片封裝（c〇b;Chip〇n board)、帶載封裝（Tape Carrier Package)、塑膠針柵陣 列（Plastic pin grid array)、塑膠球柵陣列（piastic bal 1 3 322886 201141899 g—ndarray#，係使用液狀材料而不使用模具進行密封、 ϋ = 2逐漸增加。然、而，—般使用液狀材料有著信 上pf，用於形材料低的缺點。此係因為液狀材料有黏度 、用於環氧樹脂、硬化劑、填充劑等係受到限制之故。 為克服此等問題點，為主劑之環氧樹脂及硬化劑係被 :望士低黏度化、低吸濕化、高耐熱化。以低黏度環氧樹 ^而"’係以雙紛A型環氧樹脂、雙紛F型環氧樹脂為— 般戶二熟知’惟低黏度方面並不充分。低黏度性優異之環氧 樹脂係可’醇频的環氧樹脂，惟錄係_般之醇原料 =環氧樹脂的氣量多，硬化物的财熱性、吸濕性皆為低性 月b在此以低黏度性優異、硬化物的耐熱性高之環氧樹脂 而言，可舉如三羥甲基丙烷之環氧樹脂。 以二羥甲基丙烷之環氧樹脂而言，東都化成公司製之 YH-300、Nagase ChemteX公司製之EX-318之總氯量各自 為5%以上之多，不適於電子材料用途。且有著末端基純度 低而硬化物的Tg低的問題。 【發明内容】 (發明欲解決之課題） 本發明之目的在於提供低黏度，且硬化物之耐熱性、 对濕性優異的環氧樹脂組成物及其硬化物。 (解決課題之手段） 換言之’本發明的三羥曱基丙烷之聚環氧丙基醚，係 調配以氣相層析分析之n=〇成分（三羥甲基丙烷之聚環氧 丙基驗所含有之三羥甲基丙烷環氧丙基醚單體）中的三環 4 322886 201141899 基（Triglyeidyl)體的比率為35%以上，總氯量為〇. 3 _ Y 、下於25 C的黏度為3〇〇mPa · s以下之低黏度環 ，树月曰作為必須成分的環氧樹脂組成物。#复，本發明為前 述之環氧樹腊組成物硬化而成之硬化物。 (發明之效果） 優里之環氧樹脂的環氧樹脂組成物，因其具有 又性’同時在其硬化後所得到的硬化物，係具 !=:耐熱性、耐濕性的性能，故適合用於重防飯塗料、 叙體塗料y〇!塗料、罐裝塗料等塗料用途或土木、建築 用途’接著料、電性絕緣用、半導體晶片暫時接合劑等 電子部件用途及印刷線路板或碳纖維強化塑膠 主之各種複合材料用途等，特別係可適合使用於 印刷線路板、半導體密封等之電氣/電子領域的絕緣材料 等。 【實施方式】 對本發明進行詳細說明。 於本發明之三經甲基丙燒環氧丙基喊㈣成分）中， 通常存在早環氧丙基體、二環氧丙基體、三環氧丙基體， 惟本發明之三環氧丙基體之比率係三環氧丙基 體之比率係35%以下則硬化物”等物理性質降低，且增 加樹脂黏度而為不佳，故以5()%以上為佳，以75%以上為更 佳。 本發明所使用之三 氯量係0.3重量％以下， 經甲基内燒之聚環氧丙基醚的總 以〇· 2重量％以下為佳。當總氣量 322886 5 201141899 超過0.3重量％而使用驗性的硬化促進劑時，硬化反應受到 阻礙’其結果為硬化物的物理性質降低。且引起絕緣信賴 性的降低，而不適合使用於電氣/電子領域之用途。 本發明所使用之三經甲基丙燒之聚環氧丙基喊於25 C的黏度為施Pa.s以下。當於阶的黏度超過綱心· s，則稀釋效率降低而為不佳。 本發明所使用之三經甲基丙垸之聚環氧丙基鍵，從低 黏度性之觀點來看，以㈣成分的含有率為娜以上為佳， 以70%以上為更佳，以9〇%以上為尤佳。 使三經甲基丙烧與表氣醇（Epichl〇r〇hydrin)反應的 方法’係可進行與通常之環氧化反應相同的操作。可列舉 例如：調配相對於三經甲基丙烧的經基為過量的表氣醇而 吟，後’於驗金屬氫氧化物存在下使其於反應4〇至12代 範圍反應1至10小時的方法。此時，從水解性氣減低之 觀點來看’以於50至90t進行反應為佳。 於上述反應所使用之驗金屬氫氧化物，可列舉如：氮 氧化鐘、氫氧化納、氫氧化钟、氮氧化轉等，惟特別以氮 氧化納、氫氧化卸為佳。驗類係水溶液或固體皆可，惟以 處理之容易度而言，以使用水溶液為佳。驗金屬氮氧化物 $使用量通常係相對於i當量的醇性經基為〇?至3〇當 量’以0.8至2.0當量為佳。當驗金屬氫氧化物的使用量 過夕時’則會導致促進聚合反應或副反應而使生產性變 f。此外’當過対1三Μ基狀餘⑽的反應變 传不充分’殘留未、㈣氧丙賊化之氣醇（GhiQ_drin) 322886 6 201141899 • 體，故造成末端環氧基的純度降低。 此外，上述表氯醇的使用量係相對於1當量的夕^ 的經基為1至10當量，以2至6當量為佳。當表^醇 用直少於1當量時將容易進行高分子化，而目的二的使 (Chl_hydrin 6齡）的收量變少。此外，若較=醇喊 當量，則全部裝入量相對於多元醇類之比例變得I 1〇 產性低落，故為不佳。 i侍過小而生 為了使上述反應簡便地進行，係可因 級敍鹽以作為觸媒。以可使用之第四級敍鹽而古^第四 ;基=:化1、，…基三甲:氣;舉 #2對於彳t 化銨等。以第四級銨鹽的使用量而令’诵火 係相對於使収乡元料 。通常 至1重量％為佳。 勹至iu重里/。，以〇. 1 此外，反應時係可於 具體而言，可列舉如、:環氧基反應的溶媒中進行， 甲基異丁基酮、甲基乙其本、二甲苯、苯等芳香族煙類； 醇、丁醇等醇類.土綱、環己基嗣、丙嗣等綱類；丙 二醇甲基趟等二醇：類了醇甲基醚、丙二醇甲基醚、二丙 醚等脂肪族關；二鸣c基驗、一丁基驗、乙基丙基 亞礙等，亦可將兮蓉夕Ί氯料等脂環式嶋、二甲 用量相對於表上混合使用。此等溶媒的使 至150重量份的範圍為1，份’係200重量份以下，以5 佳。 以1 〇至1 〇〇重量份的範圍為更 0%者 前述反應系統内之水分係以㈣以上、未達2. 322886 7 201141899 為佳。系統内水分若低於0.1 %則反應變得緩慢。系統内水 分若高於2. 0%以上則因水分的影響而阻礙環氧丙基醚化 反應，故含有之氣變高。 將前述反應所產生之環氧丙基醚類自反應混合物進 行單離的方法，有例如：將未反應之表氯醇及溶劑於減壓 或常壓下餾除、溶解於有機溶媒，將反應混合物中副生成 的鹼金屬鹽及過剩之鹼金屬氫氧化物以水洗、過濾等進行 分離’接著回收溶解所用的有機溶媒’得到環氧丙基醚類 的方法等。以在此使用之有機溶媒而言’可列舉如：曱基 異丁酮、曱本、一曱苯、環己基酮、甲醇、乙醇、丙醇、 丁醇等，惟其中以甲基異丁酮、甲苯及二，苯為佳，此外 亦可為此等之混合溶媒。 三經曱基丙院與表氣醇反應結束後，將過剩之表氯_ 德除、溶解於溶劑、進行賴、以水洗去除無機鹽，接著 藉由顧除溶劑而可得到本發明所用之三㈣基丙烧的聚環 氧丙基趟，惟水解性南量過多時，從水解㈣量減低的_ 點來看，將所制的私樹脂復加入相對於 殘留的水解十连 里，1至3G倍量的驗金屬氫氧化物，於⑽至赃的;』 進行1G /7知至2小時的精製反應後，以中和、水洗等2 进將過剩之驗金屬ft氣化物或副生賴鹽去除、再顧除淳 K更為讀製的本發明所使用之三經？基丙烧¥ =氧丙基醚。此外，前述反應所得之三”基丙烧的琢 ，衣氧丙基醚係可使用緩分子蒸铜精製者。 本發明之環氧㈣組絲，係以環氧樹脂及硬化齊Η 322886 8 201141899 • 為必須成分之環氧樹脂組成物，而以環氧樹脂成分而言， ，係經調配申請專利範圍第1項所述之三經曱基丙烧的聚環 氧丙基醚以作為必須成分者。 以將申請專利範圍第！項所述之三經甲基丙烧的聚環 氧丙基醚作為必須成分的硬化劑之狀況而言，係可使用一 般所知之作為環氧樹脂的硬化劑者，例如，二氰二胺 (Dicyandiamide)、多元酚類、酸酐類、芳香族及脂肪族胺 類等。 具體的例示，以多元酚類而言，有例如：雙酚A、雙 酚F、雙酚S、雙酚薙、4,4，_聯酚、2,2，_聯酚、對苯二 醌、間二酚、萘二酚等之二元酚類；或者是參_(4_羥基苯 基）曱烷、1，1，2, 2-肆（4-羥基苯基）乙烷、酚酚醛清漆 (Phenol novolac)、鄰-曱酚酚醛清漆一Cres〇1 novolac)、萘酚酚醛清漆、聚乙烯基酚等代表之三元以上 的酚類。再者，有如：酚類、萘酚類或者是雙酚A、雙酚F、 雙酚S、雙酚苐、4, 4，-聯酚、2, 2，-聯酚、對苯二醌、 間二紛、萘二盼等之二元紛類與曱酿、乙酸、苯曱醛、對_ 羥基苯曱醛、對-苯二甲醇等之縮合劑所合成的多元酚性化 合物。 以酸酐而言，有如：醜酸酐、四氫欧酸酐、曱基四氫 酞酸酐、六氫酞酸酐、曱基六氫酞酸酐、甲基腐植酸酐 (Methyl himic anhydride)、納迪克酸肝（Nadic anhydride)、苯偏三酸酐（Trimellitic anhydride)等。 以胺類而言，有如：4,4’ -二胺基二苯基甲烷、4,4，一 322886 9 201141899 一胺基一本基丙烧、4, 4 _一胺基二苯基硬、間—伸苯二 胺、對-伸苯二甲二胺等芳香族胺類；乙二胺、己二胺、二 伸乙三胺、三伸乙四胺等脂肪族胺類。 前述之公知慣用之硬化劑的使用量，相對於環氧樹脂 之官能基之環氧基1當量，硬化劑的官能基係以〇4至2.〇 當量為佳’0· 5至1_ 5當量為更佳，0.5至丨.〇當量為特佳。 相對於環氧基1當量之硬化劑係未達〇.4當量、或者多過 2.0當量時，硬化變得不完全而有無法得到良好的硬化物 之虞。本發明之環氧樹脂，组成物，係可將此等硬化劑i種 或混合2種以上使用。 此夕卜本發明之環氧樹脂組成物中，以環氧樹脂的成 刀而έ ’係、可調配本發明相關之三經曱基丙制聚環氧丙 基鍵以外的其他種環氧樹脂。以此狀況之環氧樹脂而言， 係分子中具有2個以上環氧基之通常的環氧樹脂皆可使 用。，可列舉例如··雙酚人、雙酚s、雙紛第、4, 4，_聯驗、 2, 2 _聯酚、對苯二醌、間二酚等2元酚類；或者是參_(4— 沒基苯基）乙烧、1，1，2,卜肆⑷經基苯基）乙烧、㈣酸清 漆鄰甲紛紛酿清漆等3元以上的盼類；或是四溴雙盼A 等由齒化雙紛類所衍生的環氧丙基醚化物等；聚乙二醇或 ，内二醇等醇類之聚環氧丙細類等；二胺基二苯基甲烷 =之聚環氧丙基贿等；脂環式環氧樹脂等。此等環氧樹 可1種或混合2種以上使用。係此等環氧樹脂組成物 時’關於本發明之三㈣基㈣的聚環氧丙絲之調配量 於環氧樹脂全體中為5至⑽％，以6()至丨繼之範圍為佳。 10 322886 201141899 此外’本發明之環氧樹脂組成物中’係可適當地配合 聚酯、聚醯胺、聚醯亞胺、聚酯、聚胺酯、石油樹脂、節 薰草酮樹脂（Indene coumarone resin)、笨氧樹脂等之寡 聚物或高分子化合物，亦可調配無機填充劑、顏料、難燃 劑、搖變性（Thixotropy)賦予劑、偶合劑、流動性提升劑 等添加劑。無機填充劑可列舉例如：球狀或破碎狀的熔融 氧化矽、結晶氧化矽等之氧化矽粉末，氧化鋁粉末、玻璃 粉末、雲母、滑石、碳酸|弓、氧化銘或水合氧化銘等等。 以顏料而言’有如：有機系或無機系的體質顏料、鱗片狀 顏料等。搖變性賦予劑可列舉如：聚矽氧系、蓖麻油系、 脂肪族隨胺臘、聚氧化乙烯蠟、有機膨土（Bentonite)系 等。此外’復可因應所需而於本發明之樹脂組成物使用如： 椋櫚蠟（Carnauba wax)、〇p蠟等離型劑；γ -環氧丙氧基 丙基三曱基石夕氧烷等偶合劑；碳黑等著色劑；氧化銻（111) 等難燃劑’聚石夕氧油等低應力化劑；硬脂酸約等潤滑劑。 再者’本發明之樹脂組成物係可使用公知之硬化促進 劑。可列舉例如：2-甲基咪唑、2-乙基-4-甲基咪唑等咪唑 類；2-甲基咪唑啉、2-乙基_4_甲基咪唑啉等咪唑啉類；咪 唑化合物的三啡鹽、氰基乙基鹽、氰基乙基三酸酐鹽等各 種鹽類；醋酸鋅、醋酸鈉等金屬系化合物類；四乙基氯化 銨等第四級錢鹽類；醯胺化合物類、三笨基膦等有機磷化 合物類等。此等硬化促進劑的調配比例，相對於本發明環 氧樹脂100質量份係〇 〇1至5重量份，以〇.1至2重量份 為佳。 11 322886 201141899 本發明之環氧樹脂硬化物係可藉由加熱上述之環氧 樹脂組成物而得到。以得到硬化物的方法而言，係可適合 使用澆注、注入、嵌裝、浸潰、液滴塗覆、轉注成形、壓 縮成形等’此時之溫度以通常而言，為loot至300ec之範 圍。 (實施例） 以下列舉本發明之實施例及比較例進行詳細說明。然 本發明不侷限於此等實施例。又，例中之份係意指質量份， %係意指質量％。此外，物理性質值係以下述方法進行測定。 環氧基當量係依照JIS K 7236之規定進行測定。 總氯量係依照JIS K 7243-3之規定進行測定。 黏度係依照JISK-7233，單一圓筒旋轉黏度計法進行 測定。 氣相層析測定係依照以下的條件測定。 單、二、三環氧丙基體之含有量係分別以氣相層析分 析之結果所得到的波峰的面積％表示。 裝置：島津製作所股份有限公司製造「GC-14B」 管柱：玻璃製填充管柱長度1. lm，直徑3.2mm 填充劑：silicone 0V-17 載體：choromosorb W AW-DMCS 流量調控器：氫50kPa，空氣50kPa，載體50kPa，一級 (Primary)400kPa 管柱流量：50ml/分鐘 INJECTION 溫度：280°C，FID 溫度：320°C，管柱溫度：160 12 322886 201141899 • °Cx2分鐘，升溫速度20°C/分鐘，最終管柱溫度：300°Cx 5分鐘201141899 . VI. Description of the invention: [Technical field to which the invention pertains] » The present invention relates to a low-viscosity, a small amount of organic chlorine, a high heat resistance, and a preparation of a trimethyl hydrazine propyl group (Trimethyl 〇lpr〇pane) Glycidyl ether) is a resin composition and a cured product thereof, which are essential components, and are suitable for use in an electrical/electronics industry such as an electrical insulating material such as a semiconductor sealing material. [Prior Art] The % oxygen resin has various types from liquid to solid, and is easy to handle because of its excellent reactivity with an epoxy resin and a hardener. When it is crosslinked by a hardener, it becomes A hardened resin having a large crosslink density, which exhibits excellent heat, moisture, chemical properties, electrical properties, etc., and is used in the electrical/electronic field. Epoxy resins are being widely used in industrial applications, but the performance required in recent years is gradually increasing. For example, a semiconductor sealing material in the field represented by a resin composition containing an epoxy resin as a main component, in recent years, as the semiconductor element has a higher degree of integration, the package size tends to be larger and thinner. At the same time, the 'mounting method is also progressing toward surface mounting, and it is expected to develop a material with better heat resistance for fusion welding. In addition, in the recent trend of high integration and high-density mounting, the package that has been transferred by conventional transfer is changed to a hybrid circuit (Hybrid 1C) and an on-chip package (c). 〇b;Chip〇n board), Tape Carrier Package, Plastic Pin Grid Array, Plastic Ball Grid Array (piastic bal 1 3 322886 201141899 g-ndarray#, using liquid materials) Without the use of a mold for sealing, ϋ = 2 gradually increases. However, the general use of liquid materials has a pf on the letter, which is used for the disadvantage of low material content. This is because the liquid material has viscosity and is used for epoxy resin. , hardeners, fillers, etc. are limited. To overcome these problems, the main agent epoxy resin and hardener are: low viscosity, low moisture absorption, high heat resistance. The viscosity of the epoxy tree ^ and "quot" is a pair of A-type epoxy resin, double F-type epoxy resin - the same as the common two - but low viscosity is not sufficient. Epoxy resin with excellent low viscosity Can be 'alcohol frequency epoxy resin, only recorded _ like Raw material=Epoxy resin has a large amount of gas, and the heat and hygroscopicity of the cured product are all low-grade b. Here, the epoxy resin having excellent low-viscosity and high heat resistance of the cured product may be a trihydroxyl group. Epoxy resin of methyl propane. In terms of epoxy resin of dimethylolpropane, the total chlorine content of YH-300 manufactured by Dongdu Chemical Co., Ltd. and EX-318 manufactured by Nagase ChemteX Co., Ltd. is more than 5%. It is not suitable for use in electronic materials, and has a problem that the purity of the terminal group is low and the Tg of the cured product is low. [Explanation] The object of the present invention is to provide a low viscosity, heat resistance of a cured product, and wetness. An epoxy resin composition excellent in properties and a cured product thereof. (Means for solving the problem) In other words, the polyepoxypropyl ether of trishydroxypropylpropane of the present invention is formulated by gas chromatography to analyze the n=〇 component. The ratio of tricyclic 4 322886 201141899 Triglyeidyl in the trimethylolpropane glycidyl ether monomer contained in the poly(epoxypropyl group of trimethylolpropane) is more than 35%, total chlorine The amount is 〇. 3 _ Y, the viscosity at 25 C is 3〇〇mPa The low-viscosity ring of s or less, and the resin composition of the sapphire, which is an essential component. #复, the present invention is a hardened product obtained by hardening the above-mentioned epoxy resin composition. (Effect of the invention) The epoxy resin composition of the resin is suitable for use in heavy-duty coatings and relics because it has a sclerosing property which is obtained at the same time as it is hardened, and has a heat resistance and moisture resistance. Coatings y〇! Coatings, can coatings and other coating applications, or civil and architectural applications, such as materials, electrical insulation, semiconductor wafers, temporary bonding agents, and other electronic components, and printed circuit boards or carbon fiber reinforced plastics, various composite materials, etc. In particular, it can be suitably used for insulating materials in the electrical/electronic fields such as printed wiring boards and semiconductor seals. [Embodiment] The present invention will be described in detail. In the trimethyl methacrylate epoxy propylene group (four) component of the present invention, an early epoxy propyl group, a diepoxy propyl group, a triepoxy propyl group is usually present, but the triepoxy propyl group of the present invention When the ratio of the ratio of the triepoxypropyl group is 35% or less, the physical properties such as the cured product are lowered, and the resin viscosity is increased, which is preferable, and 5 ()% or more is preferable, and 75% or more is more preferable. The amount of trichlorous used in the invention is 0.3% by weight or less, and the total amount of the polyepoxypropyl ether to be calcined in the methyl group is preferably 〇·2% by weight or less. When the total amount of gas is 322886 5 201141899, it is more than 0.3% by weight. In the case of a hardening accelerator, the hardening reaction is inhibited. As a result, the physical properties of the cured product are lowered, and the reliability of the insulation is lowered, and it is not suitable for use in the electric/electronic field. The polyepoxypropyl group of the propylene group has a viscosity of 25 C below the application rate of Pa.s. When the viscosity of the stage exceeds the core s, the dilution efficiency is lowered and is not good. Polyethylepoxy propyl bond of propylene, from the viewpoint of low viscosity It is preferable that the content of the component (4) is preferably more than 70%, more preferably 70% or more, and more preferably 9% by weight or more. The reaction of triacetin with epigas alcohol (Epichl〇r〇hydrin) is preferred. The method can be carried out in the same manner as the usual epoxidation reaction. For example, the formulation is based on an excess of the surface gas alcohol relative to the trimethyl propyl group, and the latter is present in the presence of the metal hydroxide. The method of reacting in the range of 4 to 12 generations of the reaction for 1 to 10 hours. At this time, from the viewpoint of reducing the hydrolyzable gas, it is preferred to carry out the reaction at 50 to 90 t. The hydroxide may, for example, be a nitrogen oxide clock, a sodium hydroxide, a hydrazine hydroxide, a nitrogen oxide, or the like, but it is preferably a sodium oxynitride or a hydrazine hydroxide. The aqueous solution or the solid may be treated only by treatment. In terms of easiness, it is preferred to use an aqueous solution. The amount of metal oxynitride used is usually 〇? to 3 〇 equivalent to i equivalent to 0.8 to 2.0 equivalents. When the amount of hydroxide used is too late, it will lead to the promotion of polymerization or vice The productivity should be changed to f. In addition, when the reaction of the 対1 Μ 状 ( (10) is not sufficient, the residue is not enough, and the gas is liquefied (GhiQ_drin) 322886 6 201141899 • Further, the purity of the epoxy group is decreased. Further, the above-mentioned epichlorohydrin is used in an amount of from 1 to 10 equivalents per 1 equivalent of the base group, preferably from 2 to 6 equivalents. In the case of the equivalent amount, it is easy to carry out the macromolecularization, and the target 2 has a smaller amount of (Chl_hydrin 6-years). Further, if the equivalent of the alcohol is equivalent to the equivalent amount of the alcohol, the ratio of the total amount to the polyol becomes I 1〇. It is not good for low productivity, and it is not good for it. In order to make the above reaction simple, it is possible to use salt as a catalyst. The fourth grade can be used to describe the salt and the ancient ^4; base =: 1, 1, ... base three: gas; lift #2 for 彳t ammonium. The amount of the fourth-grade ammonium salt is used to make the bonfire relative to the source. Usually, it is preferably 1% by weight.勹 to iu heavy /. Further, the reaction time may be specifically carried out in a solvent such as an epoxy group reaction, or an aromatic group such as methyl isobutyl ketone, methyl ethyl ketone, xylene or benzene. Cigarettes; alcohols such as alcohols and butanol; soils, cyclohexyl hydrazine, propyl hydrazine, etc.; diols such as propylene glycol methyl hydrazine: aliphatic groups such as alcohol methyl ether, propylene glycol methyl ether, dipropyl ether Guan; Erming c test, one-butyl test, ethyl propyl sulphate, etc., can also be used in combination with alicyclic bismuth and dimethyl hydrazine, etc. The range of such a solvent to 150 parts by weight is 1, and the part is 200 parts by weight or less, preferably 5. The range of 1 〇 to 1 〇〇 by weight is more than 0%. The water content in the above reaction system is preferably (4) or more and less than 2. 322886 7 201141899. If the moisture in the system is less than 0.1%, the reaction becomes slow. If the water content in the system is more than 2.0% or more, the epoxy propyl etherification reaction is inhibited by the influence of moisture, so that the gas contained therein becomes high. A method in which the epoxy propyl ether produced by the above reaction is isolated from the reaction mixture, for example, the unreacted epichlorohydrin and the solvent are distilled off under reduced pressure or normal pressure, dissolved in an organic solvent, and the reaction is carried out. A method in which a by-produced alkali metal salt and an excess alkali metal hydroxide in a mixture are separated by water washing, filtration, and the like, followed by recovery of an organic solvent used for dissolution to obtain a glycidyl ether. As the organic solvent to be used herein, 'methodyl isobutyl ketone, sulfonate, monophenylene, cyclohexyl ketone, methanol, ethanol, propanol, butanol, etc., but methyl isobutyl ketone is exemplified. Toluene and benzene are preferred, and a mixed solvent for this purpose can also be used. After the reaction of the gasification reaction with the surface gas alcohol is completed, the excess chlorine is dissolved, dissolved in a solvent, and the inorganic salt is removed by washing with water, and then the third used in the present invention can be obtained by taking care of the solvent. (4) Polypropylene glycol oxime of the propyl group, but when the amount of hydrolysis is too large, from the point of view of the decrease of the amount of hydrolysis (four), the prepared private resin is added to the residual hydrolysis for ten liters, 1 to 3G times the amount of metal hydroxide, from (10) to 赃; 』 After 1G / 7 to 2 hours of purification reaction, neutralize, wash, etc. 2 will be excess of metal ft gasification or by-product What is the use of the three methods of the invention for salt removal and re-consideration? Base propylene burning ¥ = oxypropyl ether. In addition, the trisylpropanone-derived oxime and the ethionyl propyl ether obtained by the above reaction can be purified by using a slow-melting copper-smelting copper. The epoxy (four)-component yarn of the present invention is epoxy resin and hardened 322886 8 201141899 • It is an epoxy resin composition of the essential component, and in the case of an epoxy resin component, it is formulated as a necessary component of the trimethylsulfanyl-fired polyepoxypropyl ether described in the first paragraph of the patent application. In the case of a hardener which is a component of the three-methylene-acrylic polyepoxypropyl ether described in the scope of the patent application, it is generally known that it is hardened as an epoxy resin. For example, dicyandiamide, polyhydric phenols, acid anhydrides, aromatic and aliphatic amines, etc. Specific examples, in the case of polyhydric phenols, for example, bisphenol A, bisphenol F , bisphenol S, bisphenol hydrazine, 4,4, _ bisphenol, 2, 2, _ bisphenol, p-benzoquinone, m-diphenol, naphthalenediol, etc.; or ginseng (4) _hydroxyphenyl)decane, 1,1,2,2-anthracene (4-hydroxyphenyl)ethane, phenol novolac (Phenol novolac), o--anthracene Phenolic novolac - Cres 〇 1 novolac), naphthol novolac, polyvinyl phenol, etc., representing more than three or more phenols. Further, such as: phenols, naphthols or bisphenol A, bisphenol F, Bisphenol S, bisphenol oxime, 4, 4,-biphenol, 2, 2,-biphenol, p-benzoquinone, di-n-bis, naphthalene, etc., binary and brewing, acetic acid, benzoquinone a polyhydric phenolic compound synthesized by a condensing agent such as an aldehyde, p-hydroxybenzofural or p-phenylenediethanol. In the case of an acid anhydride, for example, an acid anhydride, a tetrahydrogenic anhydride, a mercaptotetrahydrophthalic anhydride, or a hexahydrogen Indane anhydride, mercapto hexahydrophthalic anhydride, Methyl himic anhydride, Nadic anhydride, Trimellitic anhydride, etc. In the case of amines, for example: 4, 4 '-Diaminodiphenylmethane, 4,4, a 322886 9 201141899 monoamine-based-propenyl, 4,4-aminodiphenyl hard, m-phenylenediamine, p-phenylene An aromatic amine such as dimethyl diamine; an aliphatic amine such as ethylenediamine, hexamethylenediamine, diethylenetriamine or triamethylenetetramine. The above-mentioned known conventional hardener The amount of the functional group of the hardener is preferably from 〇4 to 2. 〇 equivalent of '0·5 to 1-5 equivalents, more preferably 0.5 to 丨.〇, based on 1 equivalent of the epoxy group of the functional group of the epoxy resin. When the amount of the curing agent per equivalent of the epoxy group is less than 4 equivalents or more than 2.0 equivalents, the curing is incomplete and a good cured product cannot be obtained. The oxy-resin and the composition may be used in combination of two or more kinds of such curing agents. In the epoxy resin composition of the present invention, the epoxy resin is formed into a knives. The invention relates to an epoxy resin other than the tris-propyl polyepoxypropyl bond. In the case of the epoxy resin in this case, a usual epoxy resin having two or more epoxy groups in the molecule can be used. For example, bisphenol, bisphenol s, bisphenol, 4, 4, _ test, 2, 2 _ biphenol, p-benzoquinone, m-diphenol, etc.; or _(4-- phenyl) Ethylene, 1,1,2, dip (4) by phenyl) ethidium, (iv) acid varnish, adjacent broth, varnish, etc., more than 3 yuan; or tetrabromo Hope that A and other epoxy propyl ether compounds derived from the styrofoam; polyethylene glycol or polyglycols of alcohols such as internal diols; diaminodiphenylmethane = Polyepoxypropyl brittle, etc.; alicyclic epoxy resin. These epoxy trees may be used alone or in combination of two or more. When the epoxy resin composition is used, the amount of the polyepoxy filaments of the third (four) group (four) of the present invention is 5 to 10% by weight in the entire epoxy resin, and the range of 6 () to the subsequent one is preferably . 10 322886 201141899 In addition, the 'epoxy resin composition of the present invention' can be suitably blended with polyester, polyamide, polyimine, polyester, polyurethane, petroleum resin, and indene coumarone resin. An oligomer or a polymer compound such as an anaerobic resin may be formulated with an additive such as an inorganic filler, a pigment, a flame retardant, a Thixotropy-imparting agent, a coupling agent, and a fluidity enhancer. Examples of the inorganic filler include cerium oxide powder such as spherical or crushed molten cerium oxide, crystalline cerium oxide, alumina powder, glass powder, mica, talc, carbonic acid, bow, oxidized or hydrated oxide. In terms of pigments, there are, for example, organic or inorganic extender pigments, scaly pigments, and the like. Examples of the shake imparting agent include polyoxyn oxide, castor oil, aliphatic amine wax, polyethylene oxide wax, and organic bentonite (Bentonite). In addition, the resin composition of the present invention can be used as needed, such as: a release agent such as Carnauba wax or 〇p wax; γ-glycidoxypropyltrimethyl sulphate; A coupling agent; a coloring agent such as carbon black; a non-flammable agent such as cerium oxide (111); a low-stressing agent such as polysulfuric acid; a lubricant such as stearic acid. Further, the resin composition of the present invention may be a known hardening accelerator. Examples thereof include imidazoles such as 2-methylimidazole and 2-ethyl-4-methylimidazole; imidazolines such as 2-methylimidazoline and 2-ethyl-4-methylimidazolium; and imidazole compounds. Various salts such as trimorphine salt, cyanoethyl salt, and cyanoethyl triacetate salt; metal compounds such as zinc acetate and sodium acetate; fourth-grade money salts such as tetraethylammonium chloride; Organophosphorus compounds such as trisylphosphines. The blending ratio of the hardening accelerator is preferably from 1 to 2 parts by weight based on 100 parts by mass of the epoxy resin of the present invention. 11 322886 201141899 The cured epoxy resin of the present invention can be obtained by heating the above epoxy resin composition. In the method of obtaining a cured product, it is suitable to use casting, injection, embedding, dipping, droplet coating, transfer molding, compression molding, etc. The temperature at this time is generally in the range of loot to 300 ec. . (Examples) Hereinafter, examples and comparative examples of the present invention will be described in detail. However, the invention is not limited to such embodiments. In addition, the part in the example means the mass part, and the % means the mass %. Further, the physical property values were measured by the following methods. The epoxy equivalent is measured in accordance with JIS K 7236. The total chlorine amount was measured in accordance with JIS K 7243-3. The viscosity was measured in accordance with JIS K-7233, single cylinder rotational viscometer method. The gas chromatography measurement was carried out in accordance with the following conditions. The content of the mono-, di-, and tri-epoxypropyl groups is represented by the area % of the peak obtained by the gas chromatography analysis. Device: "GC-14B" manufactured by Shimadzu Corporation. Column: Glass filled column length 1. lm, diameter 3.2mm Filler: silicone 0V-17 Carrier: choromosorb W AW-DMCS Flow controller: Hydrogen 50kPa, Air 50kPa, carrier 50kPa, Primary 400kPa Column flow: 50ml/min INJECTION Temperature: 280°C, FID Temperature: 320°C, column temperature: 160 12 322886 201141899 • °Cx2 minutes, heating rate 20°C /min, final column temperature: 300 ° C x 5 minutes
樣本：5wt%丙酮溶液 注入量：2aL GPC測定’係以以下條件進行測定。將n=〇含有量以GPC 分析的結果所得之波鋒面積％表示。Sample: 5 wt% acetone solution Injection amount: 2 aL GPC measurement was measured under the following conditions. The n=〇 content is expressed as % of the wave front area obtained as a result of GPC analysis.
機器：Tosoh股份有限公司GPC8220 分離管柱：以串聯連結TSKgel G2000HXL，TSKgel G2000HXL,TSKgel G1000HXL 管柱溫度：40°C 溶析液（Eluent):四氫呋喃，流速1 ml/分鐘 檢知器：RI檢知器 實施例1 在具備攪拌器、溫度計、氮氣導入裝置、滴入裝置、 冷卻管及油水分離裝置之内容量1L的玻璃燒瓶内，裝入三 經甲基丙烷（TMP)90份、表氣醇652份、二乙二醇甲基醚 65. 2份、水6. 5份，於流通氮氣的同時加熱至60。(：進行溶 解。升溫至60Ϊ後’投入99%氫氧化鈉77. 3份，於同溫度 進行反應6小時。藉由過濾去除所產生的鹽，將表氯醇餾 除’溶解於曱苯500份。升溫至8(TC後，加入49. 1%氫氧 化鈉水溶液〇. 32份及溫水1· 25份，於同溫度實施1小時 之精製反應。之後加入溫水25份進行攪拌，將分液後的樹 脂溶液脫水過濾，將曱苯蒸餾去除，得到164. 2g的環氧樹 月曰。此樹脂的環氧基當量係128g/eq、黏度150mPa . s/25 13 322886 201141899 °C、總氣0. 23%、GPC之n=〇純度為58%，氣相層析之㈣ 成分的單環氧丙基體（1GE):二環敦丙基體（2⑻：三 丙基體（3GE)比率為〇 : 6〇 : 4〇。所得樹脂的性狀係記載於 表1。 實施例2 除了將99%氫氧化納纟77 3份變更為ιΐ6〇份以外， ^㈣例1進行相同操作，得到154.5g的環氧樹脂。此樹 脂的裱氧基當量係125g/eq、總氣量為〇.25%、GpC2n=〇 純度為50%，氣相層析之n=〇成分的單：二：三環氧丙基 體比率為0 : 38 : 62。所得樹脂的性狀係記載於表卜 比較例1 除了將水由6. 5份變更為〇. 65份以外，與實施例^ 進行相同操作，得到⑽力的環氧樹脂。此樹脂的環氧基 田量係135g/eq、總氯量為〇. 25%、gpc之n=〇純度為50%， 氣相層析之n=〇成分的單：二：三環氧丙基體比率為〇 : 75 : 25。所得樹脂的性狀係記载於表j。 比較例2 東都化成股份有限公司製造yh〜3〇〇(三m甲基丙烧環 氧丙基謎）。YH-綱的環氧基當量係U2g/eq、黏度147 mPa · s/25C、總氯量為5. 0%、GPC之㈣純度為㈣，氣 相層析之n=0成分的單：二：三環氧丙基體比率為〇:81 : 19。所得樹脂的性狀係記載於表i。 322886 14 201141899 表1 實施例1 環氧樹胳A 環氧基當量 --- A 12%~~ 黏度 Ϊ5〇 總氣量 0.¾~~~ n=0(GPC 面積％) 58 π=0環氧丙基縫比 _ 1GE 2GE 60^ 3GE ' 40 實施例2 125~ 0.25 142 81 25 19 實施例3 將實施例丨所狀縣樹脂（以下稱為環氧樹脂A)使 射1；TteCh股份有限公司製造之薄膜分子蒸賴肌-4, 二壓力^、溫度125至靴進行分子蒸顧，得到環氧 树脂D。所得樹脂的性狀係記载於表2。 實施例4 將實施例2所得之環氧_(以下稱為環氧樹脂B)進 ㈣實施例3相同之分子蒸館，得到環氧樹脂£。所得樹 月曰的性狀係記载於表2。 比較例3 所得之環氧樹脂（以下稱為環氧樹脂〇進 灯與實施例3相同之分子蒸顧’得到環氧樹脂f。所得樹 脂的性狀係記载於表2。 比較例4 將東都化成股份有限公司製造之瓜3〇〇進行與實施 322886 15 201141899 例3相同之分子蒸餾，得到環氧樹脂G。所得樹脂的性狀 係記載於表2。 表2 實施例3 實施例4 比較例3 比較例4 環氧樹脂D 環氧樹脂E 環氧松脂F 環氧樹脂G 環氧基當量 120 112 127 , 132 黏度 65 55 80 72 總氯量 0.08 0.08 0. 08 3.5 n=0(GPC 面積％) 98 98 1 35 n=0環氧丙基醚比 1GE 0 0 Γ~~~~ 0 2GE ' 61 40 ΪΓ~~ 81 3GE 39 60 24 19 實施例5、6比較例5、6實施例7、8比較例7、8 將相對於東都化成股份有限公司製造之YD-8125的100 重量份之環氧樹脂A至環氧樹脂G、YH-300以成為混合黏度 1000 mPa · s/25°C之比例進行調配，以作為環氧樹脂成分。 以硬化劑而言，係使用Rikacid MH-700(曱基六氫欧酸針， 酸酐當量168g/eq，新日本理化股份有限公司製造），以硬 化促進劑而言，係使用HISHICOLIN PX-4ET(有機鱗鹽化合 物，日本化學股份有限公司製造），如表3所示進行調配， 得到環氧樹脂組成物。又，表中之數值係表示調配之重量份。 使用此環氧樹脂組成物，於l〇(TC耗時2小時而成形， 再於140eC進行12小時之後硬化（post cure；)，得到硬化 物試驗片後，提供進行各項物性測定。結果係示於表3。 又硬化物性的试驗方法及§乎估方法係如以下所述。 (1)硬化物Tg，係使用熱機械測定裝置（Seik〇電子股份有 322886 16 201141899 . 限公司製造），以10°C/分之升溫速度進行測定。 (2) 吸水率，係使用直徑50匪、厚度5mm的圓形試驗片， 以23°C、100%RH的條件使吸濕50小時候之重量增加變化 〇 (3) 離子性不純物質，係於l〇5°C、進行20小時的加壓蒸 煮實驗（Pressure cooker test)後，將萃取的離子份以離 子層析法測定氯離子，換算求出固形份。 使用環氧樹脂A、B之實施例5、6與使用環氧樹脂C 的比較例5相比，顯示了高的硬化物Tg及低的吸水率。且 與使用YH-300的比較例6相比，PCT氣的萃取量係大幅減 少。 同樣地，使用環氧樹脂D、E之實施例7、8與使用環 氧樹脂F的比較例7相比，顯示了高的硬化物Tg及低的吸 水率。且與使用環氧樹脂G的比較例8相比，PCT氯的萃 取量係大幅減少。 表3 實施例5 實施例6 峨例5 比較例6 實施例7 實施例8 啸例7 bh妨备1兌 YIH125 100 100 100 100 100 100 100 1〇〇 環脂A 40 環娜旨B 一 42 環倾脂C 39 YH-300 40 — 環細旨D 30 環脂E 26 環倾脂F 35 環脂g 33 域調se|4度(mPa · s/25°C) 1000 _ 硬化劑 133.6 137.0 130.7 128.9 124.2 121.5 128.1 124 9 _ 硬化促進劑 1.4 1.4 1.4 1.4 1.3 1.3 1.4 13 硬(t#7Tg(C) 115 117 104 106 r 118 122 105 103 硬4谈吸水率〇t%) 0.41 0.54 0.68 0.4 0.34 0.52 〇 R1 PCT氣萃取量(ppm) 0.6 0.6 0.6 8.5 0.4 卜0.4 0.4 6.3 17 322886 201141899 (產業上之可利用性） 使用本發明之環氧樹脂係可得到低黏度性優異、同時 Tg高而财濕性優異的硬化物。此係可製造在通常使用範圍 必要及充分地耐熱、濕性優異的硬化物，而可得到有用於 半導體元件所代表之電氣/電子部件等的密封、塗佈材料、 積層材料、複合材料等之樹脂組成物，其係具有技術上之 重大意義。 【圖式簡單說明】 無。 【主要元件符號說明】 無0 18 322886Machine: Tosoh Co., Ltd. GPC8220 Separation column: TSKgel G2000HXL, TSKgel G2000HXL, TSKgel G1000HXL column in series. Temperature: 40 °C Eluent: Tetrahydrofuran, flow rate 1 ml/min. Detector: RI detection Example 1 In a glass flask equipped with a stirrer, a thermometer, a nitrogen gas introduction device, a dropping device, a cooling pipe, and a water-hydraulic separation device in an amount of 1 L, 90 parts of trimethylsilane (TMP) was charged in a gas alcohol. 652 parts, diethylene glycol methyl ether 65. 2 parts, water 6.5 parts, heated to 60 while circulating nitrogen gas. (: Dissolve. After heating to 60 ', 'Inject 99% sodium hydroxide 77. 3 parts, carry out the reaction at the same temperature for 6 hours. Remove the produced salt by filtration, and distill off the epichlorohydrin' to dissolve in the benzene. After heating to 8 (TC, add 49.1% aqueous sodium hydroxide solution. 32 parts and warm water 1.25 parts, and perform the purification reaction at the same temperature for 1 hour. Then add 25 parts of warm water and stir. The resin solution after the liquid separation was dehydrated and filtered, and the toluene was distilled off to obtain 164.2 g of epoxy resin. The epoxy equivalent of the resin was 128 g/eq, and the viscosity was 150 mPa. s/25 13 322886 201141899 °C, Total gas 0.23%, GPC n = 〇 purity is 58%, gas phase chromatography (4) component of monoepoxypropyl group (1GE): bicyclodextrin (2 (8): tripropyl (3GE) ratio is 〇: 6〇: 4〇. The properties of the obtained resin are shown in Table 1. Example 2 Except that 99 parts of 99% sodium hydride hydroxide was changed to 6 parts of ιΐ, ^(4) Example 1 was subjected to the same operation to obtain 154.5 g. Epoxy resin. The epoxy equivalent of this resin is 125g/eq, the total gas volume is 25.25%, GpC2n=〇 purity is 50%, and gas chromatography is n=〇 The fraction of the single: two: triepoxypropyl group is 0: 38: 62. The properties of the obtained resin are described in Table 1. Comparative Example 1 except that water was changed from 6.5 parts to 〇. 65 parts, and examples ^ The same operation was carried out to obtain a (10) force epoxy resin. The epoxy field of the resin was 135 g/eq, the total chlorine amount was 〇. 25%, and the gpc n = 〇 purity was 50%. n = 〇 component of the single: two: triepoxypropyl ratio is 〇: 75: 25. The properties of the obtained resin are described in Table j. Comparative Example 2 Dongdu Chemical Co., Ltd. manufactures yh~3〇〇 (three m Methyl propylene oxide propylene propyl mystery. YH-class epoxy equivalent U2g / eq, viscosity 147 mPa · s / 25C, total chlorine is 5.0%, GPC (four) purity is (four), gas phase The ratio of the single: two: triepoxypropyl group of the n=0 component of the chromatography was 〇: 81: 19. The properties of the obtained resin are shown in Table i. 322886 14 201141899 Table 1 Example 1 Epoxy A A Epoxy Base equivalent--- A 12%~~ Viscosity Ϊ5〇 Total gas volume 0.3⁄4~~~ n=0(GPC area%) 58 π=0 epoxy propyl slit ratio _ 1GE 2GE 60^ 3GE ' 40 Example 2 125~ 0.25 142 81 25 19 Implementation 3 The resin of the example (hereinafter referred to as epoxy resin A) was shot at 1; the film molecule manufactured by TteCh Co., Ltd. was steamed to the muscle-4, the pressure was 125, and the temperature was 125 to the shoe for molecular evaporation. Epoxy resin D. The properties of the obtained resin are shown in Table 2. Example 4 The epoxy resin (hereinafter referred to as epoxy resin B) obtained in Example 2 was placed in the same molecular vapor column as in Example 3 to obtain an epoxy resin. The traits of the resulting tree sorghum are shown in Table 2. Comparative Example 3 The obtained epoxy resin (hereinafter referred to as an epoxy resin lamp was subjected to the same molecular distillation as in Example 3) to obtain an epoxy resin f. The properties of the obtained resin are shown in Table 2. Comparative Example 4 The melon 3 manufactured by Chemicals Co., Ltd. was subjected to molecular distillation similar to that of Example 3, 322,886, and 201141899, to obtain an epoxy resin G. The properties of the obtained resin are shown in Table 2. Table 2 Example 3 Example 4 Comparative Example 3 Comparative Example 4 Epoxy Resin D Epoxy Resin E Epoxy Resin F Epoxy Resin G Epoxy Equivalent 120 112 127 , 132 Viscosity 65 55 80 72 Total Chlorine 0.08 0.08 0. 08 3.5 n=0 (GPC Area%) 98 98 1 35 n=0epoxypropyl ether ratio 1GE 0 0 Γ~~~~ 0 2GE ' 61 40 ΪΓ~~ 81 3GE 39 60 24 19 Examples 5 and 6 Comparative Examples 5 and 6 Examples 7 and 8 Comparative Examples 7 and 8 100 parts by weight of Epoxy Resin A to Epoxy Resin G and YH-300 of YD-8125 manufactured by Dongdu Chemical Co., Ltd. were used to have a mixing viscosity of 1000 mPa · s / 25 ° C. It is formulated to be used as an epoxy resin component. In the case of a hardener, Rikacid MH-700 (mercaptohexahydrochloride) is used. In the case of a hardening accelerator, HISHICOLIN PX-4ET (organic scale salt compound, manufactured by Nippon Chemical Co., Ltd.) was used as the hardening accelerator, as shown in Table 3, and the needle was used as an acid anhydride equivalent of 168 g/eq. Formulated to obtain an epoxy resin composition. In addition, the values in the table indicate the parts by weight. The epoxy resin composition was formed by using 1 〇 (TC took 2 hours to form, and then hardened at 140 eC for 12 hours). (post cure;), after obtaining a cured test piece, the physical properties were measured. The results are shown in Table 3. The test method and the method for determining the cured physical properties are as follows. Tg is measured using a thermomechanical measuring device (Seik〇 Electronics Co., Ltd., 322886 16 201141899. Manufactured by the company) at a temperature increase rate of 10 ° C / min. (2) Water absorption rate is 50 直径 diameter and 5 mm thickness Round test piece, change the weight of moisture absorption for 50 hours under conditions of 23 ° C and 100% RH 〇 (3) Ionic impurities, which were subjected to a pressure cooking experiment at 10 ° C for 20 hours. After Pressure cooker test) The extracted ion fractions were measured by ion chromatography to determine the solid content, and the solid fractions were obtained by conversion. Examples 5 and 6 using epoxy resins A and B showed higher height than Comparative Example 5 using epoxy resin C. Hardened material Tg and low water absorption. Further, compared with Comparative Example 6 using YH-300, the extraction amount of PCT gas was drastically reduced. Similarly, Examples 7 and 8 using the epoxy resins D and E showed a higher cured product Tg and a lower water absorption ratio than Comparative Example 7 using the epoxy resin F. Further, compared with Comparative Example 8 using epoxy resin G, the extraction amount of PCT chlorine was drastically reduced. Table 3 Example 5 Example 6 Example 5 Comparative Example 6 Example 7 Example 8 Xiaowen 7 bh 1 1 YIH125 100 100 100 100 100 100 100 1 〇〇 ring grease A 40 环娜旨 B a 42 ring Pour fat C 39 YH-300 40 — ring detail D 30 ring grease E 26 ring fat F 35 ring grease g 33 domain adjustment se|4 degrees (mPa · s / 25 ° C) 1000 _ hardener 133.6 137.0 130.7 128.9 124.2 121.5 128.1 124 9 _ Hardening accelerator 1.4 1.4 1.4 1.4 1.3 1.3 1.4 13 Hard (t#7Tg(C) 115 117 104 106 r 118 122 105 103 Hard 4 talk about water absorption 〇t%) 0.41 0.54 0.68 0.4 0.34 0.52 〇 R1 PCT gas extraction amount (ppm) 0.6 0.6 0.6 8.5 0.4 Bu 0.4 0.4 6.3 17 322886 201141899 (Industrial Applicability) The epoxy resin of the present invention can be used to obtain excellent low viscosity and high Tg and richness of moisture. Excellent hardened material. In this way, it is possible to produce a cured product which is required to be excellent in heat resistance and moisture resistance in a usual use range, and to obtain a seal, a coating material, a laminate material, a composite material, or the like for an electric/electronic component represented by a semiconductor element. The resin composition is technically significant. [Simple description of the diagram] None. [Main component symbol description] None 0 18 322886