JP2020105440A - 高純度3,4−エポキシシクロヘキシルメチルメタクリレート - Google Patents
高純度3,4−エポキシシクロヘキシルメチルメタクリレート Download PDFInfo
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- JP2020105440A JP2020105440A JP2018247154A JP2018247154A JP2020105440A JP 2020105440 A JP2020105440 A JP 2020105440A JP 2018247154 A JP2018247154 A JP 2018247154A JP 2018247154 A JP2018247154 A JP 2018247154A JP 2020105440 A JP2020105440 A JP 2020105440A
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- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
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- PTMYSDNLUQKJQW-UHFFFAOYSA-N oxacyclotridecane-2,13-dione Chemical compound O=C1CCCCCCCCCCC(=O)O1 PTMYSDNLUQKJQW-UHFFFAOYSA-N 0.000 description 1
- YOURXVGYNVXQKT-UHFFFAOYSA-N oxacycloundecane-2,11-dione Chemical compound O=C1CCCCCCCCC(=O)O1 YOURXVGYNVXQKT-UHFFFAOYSA-N 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
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- 239000003504 photosensitizing agent Substances 0.000 description 1
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- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
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- 238000007789 sealing Methods 0.000 description 1
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- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
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- 239000008117 stearic acid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 description 1
- OXTXYKOWIHKUFN-UHFFFAOYSA-N tetratert-butyl 5-benzoylbenzene-1,2,3,4-tetracarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=CC(C(=O)C=2C=CC=CC=2)=C1C(=O)OOC(C)(C)C OXTXYKOWIHKUFN-UHFFFAOYSA-N 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
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- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
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Abstract
Description
本発明の他の目的は、硬化性に優れた高純度の3,4−エポキシシクロヘキシルメチルメタクリレートを提供することにある。
本発明のさらに他の目的は、透明性及び耐熱性に優れた機能材料、光学部材等の原材料として有用な硬化性組成物とその硬化物、前記硬化性組成物を含む封止剤、接着剤、コーティング剤、及び前記硬化物からなる部材を備えた光学部材を提供することにある。
本発明の製造方法によれば、上記のような優れた特性を有する脂環式エポキシ化合物製品を工業的に効率よく製造できる。
本発明の硬化物及び光学部材は、上記の硬化性組成物を硬化して製造するので、透明性及び耐熱性に優れる。
本発明の封止剤、接着剤、コーティング剤は、上記のような優れた特性を有する硬化性組成物を含むので、透明性や耐熱性等の物性に優れた硬化物を比較的短い時間で得ることができる。
本発明の脂環式エポキシ化合物製品、すなわち高純度3,4−エポキシシクロヘキシルメチルメタクリレートは、3,4−エポキシシクロヘキシルメチルメタクリレート(=下記式(i)
本発明の脂環式エポキシ化合物製品は、下記工程を経て製造することができる。なお、工程Bと工程Cは何れを先に行ってもよい。
工程A:3−シクロヘキセニルメチルメタクリレートを有機過酸でエポキシ化して反応生成物(反応粗液)を得る工程(エポキシ化工程)
工程B:反応生成物(所定の工程を経たものであってもよい)を脱低沸蒸留に付す工程(脱低沸工程)
工程C:反応生成物(所定の工程を経たものであってもよい)を脱高沸蒸留を施す工程(脱高沸工程)
エポキシ化工程は、下記式で示されるように、式(b)で表される3−シクロヘキセニルメチルメタクリレートを有機過酸と反応させて、3,4−エポキシシクロヘキシルメチルメタクリレートを生成させる工程である。本工程において、式(i)で表される3,4−エポキシシクロヘキシルメチルメタクリレートを含む反応生成物(反応粗液)が得られる。
水洗工程は、エポキシ化工程を経て得られた反応生成物中に含まれる有機過酸やその分解物である有機酸を水洗により除去する工程である。
アルカリ中和処理工程及びアルカリ水洗工程は、反応生成物中に含まれる有機過酸や有機酸等をアルカリで除去する工程である。使用するアルカリ水溶液としては、水酸化ナトリウム水溶液、水酸化カリウム水溶液、炭酸ナトリウム水溶液、炭酸水素ナトリウム水溶液などが挙げられる。アルカリ水溶液の使用量としては、例えば処理に供する反応生成物(被処理液)の0.1〜10重量倍程度である。
脱溶媒工程は、反応生成物中に含まれる溶媒を留去する工程である。脱溶媒は、通常、薄膜蒸発器、フラッシュ缶などの蒸発器が用いられる。脱溶媒は、溶媒を完全に除去するため、2段で行うのが好ましい。一段目の脱溶媒は、加熱温度50〜100℃、好ましくは50〜70℃の範囲で行うのが好ましい。1段目の脱溶媒で、溶媒濃度3〜50重量%(好ましくは10〜20重量%)の缶出液が得られる。2段目の脱溶媒は、加熱温度50〜100℃、好ましくは50〜70℃の範囲で行うのが好ましい。2段目の脱溶媒で、溶媒濃度が例えば1重量%以下の缶出液が得られる。
脱低沸工程は、反応生成物中に含まれる、3,4−エポキシシクロヘキシルメチルメタクリレートよりも低沸点の成分(例えば、溶媒、水分、低沸点不純物)を留去する工程である。本工程により、脂環式エポキシ化合物製品中に混入する前記式(a)〜(c)で表される化合物の含有量を極めて低く低減することができる。前記式(a)〜(c)で表される化合物の含有量を低減することにより、得られる脂環式エポキシ化合物製品の着色や経時的な着色を抑制できるとともに、当該脂環式エポキシ化合物製品を含む硬化性組成物を硬化して得られる硬化物の物性、特に透明性及び耐熱性、機械的特性などを向上させることができる。
脱高沸工程は、反応生成物中に含まれる3,4−エポキシシクロヘキシルメチルメタクリレートよりも高沸点の成分を、例えば塔底から分離除去する工程である。本工程により、脂環式エポキシ化合物製品に混入する前記式(d)で表される化合物や重合物を極めて低く低減できる。前記式(d)で表される化合物や重合物の含有量を低減することにより、得られる脂環式エポキシ化合物製品を含む硬化性組成物の硬化物の物性、特に透明性及び耐熱性、機械的特性などを向上させることができる。
本発明の硬化性組成物は、前記の脂環式エポキシ化合物製品(高純度3,4−エポキシシクロヘキシルメチルメタクリレート)を含む。
(1)分子内に脂環を構成する隣接する2つの炭素原子と酸素原子とで構成されるエポキシ基(本明細書においては、「脂環エポキシ基」と称する場合がある。脂環エポキシ基には、例えば、シクロヘキセンオキシド基等が含まれる)を有する化合物(3,4−エポキシシクロヘキシルメチルメタクリレートを除く)
(2)脂環にエポキシ基が直接単結合で結合している化合物
(3)分子内に脂環及びグリシジルエーテル基を有する化合物(グリシジルエーテル型エポキシ化合物)
前記硬化剤(B)としては、例えば、酸無水物類(酸無水物系硬化剤)、アミン類(アミン系硬化剤)、ポリアミド樹脂、イミダゾール類(イミダゾール系硬化剤)、ポリメルカプタン類(ポリメルカプタン系硬化剤)、フェノール類(フェノール系硬化剤)、ポリカルボン酸類、ジシアンジアミド類、有機酸ヒドラジド等のエポキシ樹脂用硬化剤として公知乃至慣用の硬化剤を使用することができる。これらは1種を単独で又は2種以上を組み合わせて使用することができる。
本発明の硬化性組成物が硬化剤(B)を含む場合には、さらに硬化促進剤(C)を含むことが好ましい。硬化促進剤(C)は、エポキシ基(オキシラニル基)を有する化合物が硬化剤(B)と反応する際に、その反応速度を促進する効果を有する。
本発明の硬化性組成物は、硬化剤(B)に代えて、硬化触媒(D)を含んでいてもよい。硬化触媒(D)は、3,4−エポキシシクロヘキシルメチルメタクリレート等の硬化性(重合性)化合物の硬化反応(重合反応)を開始及び/又は促進させることにより、硬化性組成物を硬化させる働きを有する。硬化触媒(D)としては、例えば、光照射や加熱処理等を施すことによりカチオン種を発生して、重合を開始させるカチオン重合開始剤(光カチオン重合開始剤、熱カチオン重合開始剤等)や、ルイス酸・アミン錯体、ブレンステッド酸塩類、イミダゾール類、ラジカル重合開始剤(光ラジカル重合開始剤、熱ラジカル重合開始剤)等が挙げられる。これらは1種を単独で又は2種以上を組み合わせて使用することができる。
本発明の硬化物は、上述の硬化性組成物を硬化させることにより得られる。本発明の硬化物には、本発明の硬化性組成物をカチオン重合して得られる硬化物、本発明の硬化性組成物をラジカル重合して得られる硬化物、及び本発明の硬化性組成物をカチオン重合及びラジカル重合して得られる硬化物が含まれる。本発明の硬化物(特に、カチオン重合して得られる硬化物、又は、カチオン重合及びラジカル重合して得られる硬化物)は、透明性及び耐熱性に優れる。
光線透過率の維持率=(加熱後の硬化物の光線透過率)/(加熱前の硬化物の光線透過率)×100
本発明の封止剤は、上記硬化性組成物を含むことを特徴とする。本発明の封止剤は、光半導体装置における光半導体(光半導体素子)を封止する用途に好ましく使用できる。本発明の封止剤を使用すれば、透明性及び耐熱性に優れた硬化物(=封止材)により光半導体素子を封止することができる。
本発明の接着剤は、上記硬化性組成物を含むことを特徴とする。本発明の接着剤は、部材等を被着体に接着・固定する用途、詳細には、光半導体装置において光半導体素子を金属製の電極に接着及び固定するためのダイアタッチペースト剤;カメラ等のレンズを被着体に固定したり、レンズ同士を貼り合わせたりするためのレンズ用接着剤;光学フィルム(例えば、偏光子、偏光子保護フィルム、位相差フィルム等)を被着体に固定したり、光学フィルム同士又は光学フィルムとその他のフィルムとを貼り合わせたりするための光学フィルム用接着剤等の、優れた透明性及び耐熱性が要求される各種用途に使用することができる。
本発明のコーティング剤は、上記硬化性組成物を含むことを特徴とする。本発明のコーティング剤は、特に、優れた透明性及び耐熱性が要求される各種用途に使用することができる。
本発明の光学部材は、上述の硬化性組成物の硬化物を備えることを特徴とする。前記光学部材としては、例えば、光半導体素子が上述の硬化性組成物の硬化物によって封止された光半導体装置、上述の硬化性組成物の硬化物によって光半導体素子が電極に接着された光半導体装置、及び上述の硬化性組成物の硬化物によって光半導体素子が電極に接着され、なおかつ、当該光半導体素子が上述の硬化性組成物の硬化物によって封止された光半導体装置等が挙げられる。本発明の光学部材は、上述の硬化性組成物の硬化物によって封止され、接着された構成を有するため、耐熱性に優れ、光取り出し効率が高い。
光線透過率の維持率=(加熱後の光学部材の光線透過率)/(加熱前の光学部材の光線透過率)×100
(エポキシ化工程)
攪拌機および冷却用ジャケットが付いた内容量20リットルのSUS316製反応器にシクロヘキセニルメチルメタクリレート(以後CHMAと略する)3000g、酢酸エチル11000g、ハイドロキノンモノメチルエーテル1.2g、トリポリリン酸ナトリウム9.0gを加え、かつ反応器に挿入管から酸素/チッ素(10/9 0容量%)の混合ガスを32Nリットル/Hrで吹込んだ。次いで反応温度を40℃に保ち、30%過酢酸溶液5166gを定量ポンプで3時間かけて仕込んだ。仕込み終了後、さらに5時間熟成後反応を終了させた。このようにして3,4−エポキシシクロヘキシルメチルメタクリレート(以後METHBと略する)を含む反応粗液19167gを得た。
ロータ外径46cm,ロータ内径25mmのロータを4000回転させている遠心抽出器に軽液入口よりMETHBを含む反応粗液を2108g/分の速度で仕込むと同時に、重液入口より水を3590g/分の速度で仕込むことにより、軽液出口より軽液を166 4g/分の速度で、重液出口より重液を4034g/分の速度で得た。得られた軽液を再度同じ遠心抽出器に2108g/分の速度で仕込むと同時に、重液入口より水を3590g/分の速度で仕込むことにより、軽液出口より軽液を1877g/分の速度で、重液出口より重液を3821g/分の速度で得た。軽液中の酢酸、過酢酸濃度はそれぞれ400ppm,150ppmであった。
このようにして得られた軽液を攪拌機および冷却用ジャケットが付いた内容量15リットルのSUS316製処理槽に3000g仕込み、そこに1%NaOH水溶液を3000g仕込み、温度を10℃に保ちながら1時間攪拌をした。得られた粗液中の残存過酢酸濃度は100ppm以下であった。
次にこの軽液2790gにハイドロキノンモノメチルエーテル0.16gを加え、SUS製スミス式薄膜蒸発器で1段目の脱溶媒を行った。操作条件は加熱温度60℃、圧力150mmHgで、塔底液排出ラインから酸素/窒素の混合ガスを32リットル/Hrで吹き込んだ。この塔底液を加熱温度60℃、圧力40mmHgの条件で2段目の脱溶媒を行い、塔底液排出ラインから、酸素/窒素(10/90容量%)の混合ガスを32Nリットル/Hrで吹込んだ。得られた塔底液は538gであった。また、ガスクロマトグラフィー分析で塔底液の組成を調べたところMETHB96.4%であった。HT(ヘプタンテスト)を行なった結果、ポリマー含量は0.01%であった。
上記の方法で得られたMETHB(純度96.4%)に重合禁止剤(N−ニトロソ−N,N−ジフェニルアミン)を0.03%添加した。これを、実段数20段の多孔板塔(塔径50mm)(脱低沸物蒸留塔)の下から10段目に100重量部/Hrの流量で連続的に供給し、塔頂圧力0.1mmHg、塔頂温度80℃、塔底温度100℃、加熱温度120℃、還流比3の条件で脱低沸蒸留を行った。塔底缶出液の流量は90重量部/Hr、塔頂留出液の流量は10重量部/Hrであった。
脱低沸工程で得られた塔底缶出液を、実段数20段の多孔板塔(塔径50mm)(脱高沸物蒸留塔)の下から10段目に100重量部/Hrの流量で連続的に供給し、塔頂圧力0.1mmHg、塔頂温度80℃、塔底温度110℃、加熱温度130℃、還流比3の条件で脱高沸蒸留を行った。塔底缶出液の流量は10重量部/Hr、塔頂留出液の流量は90重量部/Hrであった。前記塔頂留出液を回収して脂環式エポキシ化合物製品1を得た。
脱低沸物蒸留塔の還流比を1、脱高沸物蒸留塔の還流比を1とした以外は、実施例1と同様にして、脂環式エポキシ化合物製品2を得た。
脱溶媒工程の塔底缶出液を、実段数10段の多孔板塔(塔径50mm)(脱低沸物蒸留塔)の下から5段目に仕込み、続いて、脱低沸物蒸留塔の缶出液を、実段数10段の多孔板塔(塔径50mm)(脱高沸物蒸留塔)の下から5段目に仕込んだ以外は、実施例1と同様にして、脂環式エポキシ化合物製品3を得た。
脱溶媒工程の塔底缶出液を、実段数5段の多孔板塔(塔径50mm)(脱低沸物蒸留塔)の下から2段目に仕込み、続いて、脱低沸物蒸留塔の缶出液を、実段数5段の多孔板塔(塔径50mm)(脱高沸物蒸留塔)の下から2段目に仕込んだ以外は、実施例1と同様にして、脂環式エポキシ化合物製品4を得た。
脱溶媒工程の塔底缶出液を、実段数10段の多孔板塔(塔径50mm)(脱低沸物蒸留塔)の下から5段目に仕込み、塔頂温度110℃、塔底温度140℃、加熱温度160℃の条件で脱低沸蒸留し、続いて、脱低沸物蒸留塔の缶出液を、実段数10段の多孔板塔(塔径50mm)(脱高沸物蒸留塔)の下から5段目に仕込み、塔頂温度110℃、塔底温度150℃、加熱温度170℃の条件で脱高沸蒸留した以外は、実施例1と同様にして、脂環式エポキシ化合物製品5を得た。
(1)純度及び不純物含有量
実施例及び比較例で得られた各脂環式エポキシ化合物製品について、3,4−エポキシシクロヘキシルメチルメタクリレート[式(i)で表される化合物]の純度、式(a)で表される化合物[=化合物(a)]、式(b)で表される化合物[=化合物(b)]、式(c)で表される化合物[=化合物(c)]、及び式(d)で表される化合物[=化合物(d)]の各含有量を、下記の条件でガスクロマトグラフを用いて測定し、面積%で算出した。
<測定条件>
測定装置:商品名「GC−2014」、島津製作所社製
カラム充填剤:(15%PEG−20M)UniportHPS
カラムサイズ:長さ2.1m×内径3.2mmφ
カラム温度:100℃→(10℃/分で昇温)→210℃(29分保持)
検出器:TCD
実施例及び比較例で得られた各脂環式エポキシ化合物製品について、着色度をハーゼン色数(APHA)を求めることにより評価した。
実施例及び比較例で得られた各脂環式エポキシ化合物製品を30℃で1ヶ月間保存した後のハーゼン色数(APHA)を測定し、ハーゼン色数(APHA)の増加割合(1ヶ月保存後のハーゼン指数/製造直後のハーゼン指数)を求め、各脂環式エポキシ化合物製品の保存安定性を下記の基準で評価した。
○:2倍未満
×:2倍以上
下記表2〜4に示す処方(単位:重量部)によって各成分を配合し、自公転式撹拌装置(商品名「あわとり練太郎AR−250」、(株)シンキー製)を使用して撹拌し、さらに脱泡して硬化性組成物を得た。
各硬化性組成物を型に充填し、所定温度の樹脂硬化オーブンで所定時間加熱することで硬化物を得、得られた硬化物のガラス転移温度、透明性を下記方法で評価した。なお、硬化の際の硬化条件は以下の通りである。
実施例4〜6、比較例3〜4:120℃×5時間
実施例7〜9、比較例5〜6:80℃×2時間、さらに140℃×2時間
実施例10〜12、比較例7〜8:80℃×2時間、さらに110℃×3時間
硬化物のガラス転移温度を下記条件で求めた。
<測定条件>
サンプル:長さ4mm×幅5mm×厚み10mm
測定装置:熱機械測定装置(TMA)、商品名「TMA/SS6000」、セイコーインスツルメント(株)製
測定モード:圧縮(針入)、定荷重測定
測定温度:25℃から300℃まで
昇温速度:5℃/分
硬化物(厚み:3mm)の波長400nmの光の光線透過率(厚み方向;%T)を、分光光度計(商品名「UV−2400」、(株)島津製作所製)を用いて測定した。
実施例4〜6、比較例3〜4について
○:Tgが70℃以上、且つ透明性が70%以上である
×:Tgが70℃未満、又は透明性が70%未満である
実施例7〜9、比較例5〜6について
○:Tgが60℃以上、且つ透明性が70%以上である
×:Tgが60℃未満、又は透明性が70%未満である
実施例10〜12、比較例7〜8について
○:Tgが140℃以上、且つ透明性が90%以上である
×:Tgが140℃未満、又は透明性が90%未満である
光半導体のリードフレーム(InGaN素子、3.5mm×2.8mm)に、各硬化性組成物を注型した後、120℃のオーブンで5時間加熱することで、前記硬化性組成物の硬化物により光半導体素子が封止された光半導体装置を得た(図1参照)。得られた光半導体装置の明るさ、及び耐熱性を評価した。
光半導体装置の明るさ(ルーメン:lm)は、光半導体装置の全光束を全光束測定機(商品名「マルチ分光放射測定システム OL771」、オプトロニックラボラトリーズ社製)を使用して測定した。
光半導体装置の耐熱性は、光半導体装置を120℃で300時間の加熱処理(エージング)に付して、光線透過率の保持率を下記式から算出し、これを耐熱性の指標とした。
光線透過率の保持率(%)=(加熱処理後の光半導体装置の光線透過率/加熱処理前の光半導体装置の光線透過率)×100
実施例4〜6、比較例3〜4について
○:明るさが0.60lm以上、且つ耐熱性が70%以上である
×:明るさが0.60lm未満、又は耐熱性が70%未満である
実施例7〜9、比較例5〜6について
○:明るさが0.60lm以上、且つ耐熱性が70%以上である
×:明るさが0.60lm未満、又は耐熱性が70%未満である
実施例10〜12、比較例7〜8について
○:明るさが0.70lm以上、且つ耐熱性が80%以上である
×:明るさが0.70lm未満、又は耐熱性が80%未満である
各硬化性組成物をコーティング剤として用いた。その反応性を下記の方法により評価した。
各硬化性組成物(コーティング剤)の反応性を、ゲルタイム測定装置(商品名「No.153 ゲルタイムテスター(マグネット式)」、(株)安田精機製作所製)を用いて測定した。なお、実施例4〜6及び比較例3〜4では120℃で加熱した際の反応性(硬化性;ゲルタイム)を評価し、実施例7〜12及び比較例5〜8では80℃で加熱した際の反応性(硬化性;ゲルタイム)を評価した。
実施例4〜6、比較例3〜4について
○:120℃ゲルタイムが2400秒以内である
×:120℃ゲルタイムが2400秒を超える
実施例7〜9、比較例5〜6について
○:80℃ゲルタイムが2000秒以内である
×:80℃ゲルタイムが2000秒を超える
実施例10〜12、比較例7〜8について
○:80℃ゲルタイムが900秒以内である
×:80℃ゲルタイムが900秒を超える
・MH−700:硬化剤、4−メチルヘキサヒドロ無水フタル酸/ヘキサヒドロ無水フタル酸=70/30、商品名「リカシッド MH−700」、新日本理化(株)製
・18X:硬化促進剤、特殊アミン、商品名「U−CAT 18X」、サンアプロ(株)製
・SI−100L:硬化触媒(熱カチオン重合開始剤)、商品名「サンエイドSI−100L」、三新化学工業(株)製
・パーブチルO:硬化触媒(ラジカル重合開始剤)
2 光半導体素子の封止材
3 ボンディングワイヤ
4 光半導体素子
5 ダイボンディング材
6 金属配線
Claims (12)
- ハーゼン色数が25以下である請求項1〜3のいずれか1項に記載の脂環式エポキシ化合物製品。
- 請求項1〜4のいずれか1項に記載の脂環式エポキシ化合物製品を含む硬化性組成物。
- さらに、硬化剤と硬化促進剤とを含む請求項5記載の硬化性組成物。
- さらに、硬化触媒を含む請求項5記載の硬化性組成物。
- 請求項5〜7のいずれか1項に記載の硬化性組成物の硬化物。
- 請求項5〜7のいずれか1項に記載の硬化性組成物を含む封止剤。
- 請求項5〜7のいずれか1項に記載の硬化性組成物を含む接着剤。
- 請求項5〜7のいずれか1項に記載の硬化性組成物を含むコーティング剤。
- 請求項8記載の硬化物からなる部材を備えた光学部材。
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JP2852673B2 (ja) | 1988-12-13 | 1999-02-03 | ダイセル化学工業株式会社 | エポキシ化された(メタ)アクリレートの製造方法 |
US5382676A (en) * | 1991-08-28 | 1995-01-17 | Daicel Chemical Industries, Ltd. | Purified 3,4-epoxycyclohexyl methyl(meth)acrylate, a process for the preparation thereof and a 3,4-epoxycyclohexyl methyl(meth)acrylate composition |
JPH08245511A (ja) | 1995-03-06 | 1996-09-24 | Daicel Chem Ind Ltd | (メタ)アクリレ―ト化合物の精製方法 |
JP3602620B2 (ja) | 1995-09-01 | 2004-12-15 | ダイセル化学工業株式会社 | 3,4−エポキシシクロヘキシルメチル(メタ)アクリレ−トの精製方法 |
RU2744632C2 (ru) | 2016-07-15 | 2021-03-12 | Басф Се | Способ получения гранул, содержащих mgda и glda, гранулы и их применение |
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WO2018110297A1 (ja) * | 2016-12-12 | 2018-06-21 | 株式会社Adeka | 組成物 |
CN108299343A (zh) * | 2018-02-09 | 2018-07-20 | 江苏泰特尔新材料科技有限公司 | 一种用微通道反应器制备(甲基)丙烯酸-3,4-环氧环己基甲酯的方法 |
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CN113227062A (zh) | 2021-08-06 |
WO2020138052A1 (ja) | 2020-07-02 |
TW202035381A (zh) | 2020-10-01 |
US20220089808A1 (en) | 2022-03-24 |
US11932723B2 (en) | 2024-03-19 |
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