JP5787202B2 - ポリエステルポリオール、ラミネート接着剤用ポリオール剤、樹脂組成物、硬化性樹脂組成物、ラミネート用接着剤、及び太陽電池用バックシート - Google Patents
ポリエステルポリオール、ラミネート接着剤用ポリオール剤、樹脂組成物、硬化性樹脂組成物、ラミネート用接着剤、及び太陽電池用バックシート Download PDFInfo
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- JP5787202B2 JP5787202B2 JP2015513931A JP2015513931A JP5787202B2 JP 5787202 B2 JP5787202 B2 JP 5787202B2 JP 2015513931 A JP2015513931 A JP 2015513931A JP 2015513931 A JP2015513931 A JP 2015513931A JP 5787202 B2 JP5787202 B2 JP 5787202B2
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- polyester polyol
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- 239000011342 resin composition Substances 0.000 title claims description 38
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- 239000012939 laminating adhesive Substances 0.000 title claims description 21
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- 150000003077 polyols Chemical class 0.000 title description 9
- 239000000853 adhesive Substances 0.000 claims description 41
- 230000001070 adhesive effect Effects 0.000 claims description 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- -1 alkylene diol Chemical class 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 30
- 125000001931 aliphatic group Chemical group 0.000 claims description 28
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
- 239000002994 raw material Substances 0.000 claims description 8
- 238000010030 laminating Methods 0.000 claims description 5
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- 239000011888 foil Substances 0.000 claims description 2
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- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 7
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- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
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- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
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- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 4
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
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- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 description 2
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- QCNWZROVPSVEJA-UHFFFAOYSA-N Heptadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCC(O)=O QCNWZROVPSVEJA-UHFFFAOYSA-N 0.000 description 2
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Images
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- 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
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
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- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
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- C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
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- 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
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- C08G63/127—Acids containing aromatic rings
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- 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
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- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/06—Polyurethanes from polyesters
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- C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/04—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof adapted as photovoltaic [PV] conversion devices
- H01L31/042—PV modules or arrays of single PV cells
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C09J2203/322—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of solar panels
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
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- Health & Medical Sciences (AREA)
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- Polymers & Plastics (AREA)
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- Electromagnetism (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Wood Science & Technology (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Photovoltaic Devices (AREA)
- Polyesters Or Polycarbonates (AREA)
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Description
斯かる炭素原子数8〜20の長鎖脂肪族ジカルボン酸は、スベリン酸、アゼライン酸、セバシン酸、ウンデカン二酸、ドデカン二酸、トリデカン二酸、テトラデカン二酸、ペンタデカン二酸、ヘキサデカンニ酸、ヘプタデカン二酸、オクタデカン二酸、ノナデカン二酸、イコサン二酸等が挙げられる。
カラム ;東ソー株式会社製 TSK−GUARDCOLUMN SuperHZ−L
+東ソー株式会社製 TSK−GEL SuperHZM−M×4
検出器 ;RI(示差屈折計)
データ処理;東ソー株式会社製 マルチステーションGPC−8020modelII
測定条件 ;カラム温度 40℃
溶媒 テトラヒドロフラン
流速 0.35ml/分
標準 ;単分散ポリスチレン
試料 ;樹脂固形分換算で0.2質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
カラム ;東ソー株式会社製 TSK−GUARDCOLUMN SuperHZ−L
+東ソー株式会社製 TSK−GEL SuperHZM−M×4
検出器 ;RI(示差屈折計)
データ処理;東ソー株式会社製 マルチステーションGPC−8020modelII
測定条件 ;カラム温度 40℃
溶媒 テトラヒドロフラン
流速 0.35ml/分
標準 ;単分散ポリスチレン
試料 ;樹脂固形分換算で0.2質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
攪拌棒、温度センサー、精留管を有するフラスコに、ネオペンチルグリコール788部、トリメチロールプロパン21部、イソフタル酸578部、無水フタル酸272部、セバシン酸419部、無水トリメリット酸17部及び有機チタン化合物0.2部を仕込み、乾燥窒素をフラスコ内に流入させ攪拌しながら230〜250℃に加熱しエステル化反応を行った。酸価が1.0mgKOH/g以下となったところで反応を停止し、100℃まで冷却後、酢酸エチルで固形分62%に希釈して、重量平均分子量(Mw)が48,000、分子量分布(Mw/Mn)が4.5、水酸基価が19、ガラス転移点(Tg)が10℃のポリエステルポリオール(A1)を得た。
攪拌棒、温度センサー、精留管を有するフラスコに、ネオペンチルグリコール836部、イソフタル酸588部、無水フタル酸274部、セバシン酸406部、無水トリメリット酸15.2部及び有機チタン化合物0.2部を仕込み、乾燥窒素をフラスコ内に流入させ攪拌しながら230〜250℃に加熱しエステル化反応を行った。酸価が1.0mgKOH/g以下となったところで反応を停止し、100℃まで冷却後、酢酸エチルで固形分62%に希釈して、重量平均分子量(Mw)が25,000、分子量分布(Mw/Mn)が3.2、水酸基価が10、ガラス転移点(Tg)が6℃のポリエステルポリオール(A2)を得た。得られたポリエステルポリオール(A2)のGPCチャート図を図1に、赤外線吸収スペクトル図を図2に示す。
攪拌棒、温度センサー、精留管を有するフラスコに、ネオペンチルグリコール794部、イソフタル酸511部、無水フタル酸272部、セバシン酸230部、ドデカン二酸261部、無水トリメリット酸21部及び有機チタン化合物0.2部を仕込み、乾燥窒素をフラスコ内に流入させ攪拌しながら230〜250℃に加熱しエステル化反応を行った。酸価が1.0mgKOH/g以下となったところで反応を停止し、100℃まで冷却後、酢酸エチルで固形分62%に希釈して、重量平均分子量(Mw)が24,000、分子量分布(Mw/Mn)が3.5、水酸基価が18、ガラス転移点(Tg)が−5℃のポリエステルポリオール(A3)を得た。
攪拌棒、温度センサー、精留管を有するフラスコに、ネオペンチルグリコール1088部、イソフタル酸727部、無水フタル酸353部、セバシン酸524部及び有機チタン化合物0.2部を仕込み、乾燥窒素をフラスコ内にフローさせ攪拌しながら240〜260℃に加熱しエステル化反応を行った。酸価が0.5mgKOH/g以下となったところで反応を停止し、100℃まで冷却後、酢酸エチルで固形分62%に希釈して、重量平均分子量(Mw)が78,000、分子量分布(Mw/Mn)が2.5、水酸基価が5、ガラス転移点(Tg)が−10℃のポリエステルポリオール(a1)を得た。
攪拌棒、温度センサー、精留管を有するフラスコに、ネオペンチルグリコール843部、イソフタル酸519部、無水フタル酸694部及び有機チタン化合物0.02部を仕込み、乾燥窒素をフラスコ内に流入させ攪拌しながら230〜250℃に加熱しエステル化反応を行った。酸価が1.0mgKOH/g以下となったところで反応を停止し、100℃まで冷却後、酢酸エチルで固形分62%に希釈して、重量平均分子量(Mw)が13,000、分子量分布(Mw/Mn)が2.2、水酸基価が20、ガラス転移点(Tg)が35℃のポリエステルポリオール(a2)を得た。
攪拌棒、温度センサー、精留管を有するフラスコに、ネオペンチルグリコール862部、イソフタル酸389部、無水フタル酸520部、アジピン酸313部及び有機チタン化合物0.02部を仕込み、乾燥窒素をフラスコ内に流入させ攪拌しながら230〜250℃に加熱しエステル化反応を行った。酸価が1.0mgKOH/g以下となったところで反応を停止し、100℃まで冷却後、酢酸エチルで固形分62%に希釈して、重量平均分子量(Mw)が15,000、分子量分布(Mw/Mn)が2.1、水酸基価が18、ガラス転移点(Tg)が20℃のポリエステルポリオール(a3)を得た。
攪拌棒、温度センサー、精留管を有するフラスコに、ネオペンチルグリコール1130部、イソフタル酸759部、無水フタル酸342部、セバシン酸534部及び有機チタン化合物1.2部を仕込み、乾燥窒素をフラスコ内にフローさせ攪拌しながら230〜250℃に加熱しエステル化反応を行った。酸価が1.0mgKOH/g以下となったところで反応を停止し、100℃まで冷却後、酢酸エチルで固形分80%に希釈した。次いで、ヘキサメチレンジイソシアネート108部を仕込み、乾燥窒素をフラスコ内にフローさせ攪拌しながら70〜80℃に加熱しウレタン化反応を行った。イソシアネート含有率0.3%以下となったところで反応を停止し、数平均分子量が10000、重量平均分子量が22000で、水酸基価が9のポリエステルポリオールを得た。これを酢酸エチルで希釈して得られた固形分62%の樹脂溶液をポリエステルポリオール(a4)とする。
多官能エポキシ化合物(B1)として、数平均分子量(Mn)470、エポキシ当量245g/eqのビスフェノールA型エポキシ樹脂(DIC株式会社製「EPICLON 860」)、多官能エポキシ化合物(B2)として数平均分子量(Mn)900、エポキシ当量475g/eqのビスフェノールA型エポキシ樹脂(三菱化学社製「JER1001」)、ポリカーボネート(C)として数平均分子量約1000、水酸基価約110であるプラクセルCD210(ダイセル化学社製)を用い、表1及び表2に従い、接着剤主剤を調製した。
接着剤硬化剤のポリイソシアネートとして、ヌレートタイプのヘキサメチレンジイソシアネート(D)スミジュールN3300(住友バイエルウレタン社製)を使用した。
表1,表2に示す配合で、ポリエステルポリオール、エポキシ化合物及びポリカーボネートを含有する主剤、硬化剤を一括混合して、各接着剤を調製した。尚、表中の配合量は固形分質量部であり、硬化剤の配合量は、主剤100質量部に対する配合量である。
原反として125μm厚のPETフィルム(東レ(株)製「X10S」)を用い、上記の各接着剤組成物を5〜6g/m2(乾燥質量)に塗装して、貼合用フィルムとして25μm厚のフッ素フィルム(旭硝子(株)アフレックス25PW)を用い、評価サンプルを得た。評価サンプルは、50℃、72時間、エージングした後、評価に供した。
評価1:外観 前記方法で作成した評価サンプルについて、フッ素フィルム側よりラミネート外観を目視評価した。
○:フィルム表面が平滑 △:フィルム表面に若干のクレーターが存在 ×:フィルム表面に多数のクレーター(凹み)が存在
評価サンプルの初期の接着力と、121℃、湿度100%環境下で25時間、50時間、75時間暴露した後のサンプルの接着力を測定した。
Claims (7)
- 分岐アルキレンジオール、炭素原子数8〜20の長鎖脂肪族ジカルボン酸、芳香族トリカルボン酸を反応させて得られる樹脂構造を有し、かつ、重量平均分子量(Mw)が10,000〜100,000の範囲、分子量分布(Mw/Mn)が3.0〜4.7の範囲にあるポリエステルポリオール(A)、及び多官能エポキシ化合物(B)を必須成分とすることを特徴とする樹脂組成物。
- 前記ポリエステルポリオール(A)が、分岐アルキレンジオール、炭素原子数8〜20の長鎖脂肪族ジカルボン酸、及び芳香族トリカルボン酸に加え、更に芳香族ジカルボン酸を原料成分として用い反応させて得られるものである、請求項1記載の樹脂組成物。
- 前記ポリエステルポリオール(A)が、水酸基価が2〜30mgKOH/gの範囲にある請求項1記載の樹脂組成物。
- 更に水酸基含有脂肪族ポリカーボネート(C)を必須成分とする請求項1記載の樹脂組成物。
- 請求項1〜4の何れか1項記載の樹脂組成物を主剤として用い、かつ、硬化剤として脂肪族ポリイソシアネート(D)を配合してなる硬化性樹脂組成物。
- 請求項5記載の硬化性樹脂組成物からなる2液型ラミネート用接着剤。
- ポリエステルフィルム、フッ素系樹脂フィルム、ポリオレフィンフィルム及び金属箔からなる群から選ばれる1種類以上のフィルムと、これらのフィルム同士を貼り合わせる為の請求項6記載の2液型ラミネート用接着剤からなる接着層とから成形された太陽電池用バックシート。
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