JP2022532260A - 無溶媒接着剤組成物およびそれを調製するための方法 - Google Patents
無溶媒接着剤組成物およびそれを調製するための方法 Download PDFInfo
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- JP2022532260A JP2022532260A JP2021574772A JP2021574772A JP2022532260A JP 2022532260 A JP2022532260 A JP 2022532260A JP 2021574772 A JP2021574772 A JP 2021574772A JP 2021574772 A JP2021574772 A JP 2021574772A JP 2022532260 A JP2022532260 A JP 2022532260A
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- Prior art keywords
- isocyanate
- reactive
- weight
- adhesive composition
- solvent
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- Granted
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- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 1
- PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 0.000 description 1
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- PYBNTRWJKQJDRE-UHFFFAOYSA-L dodecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O PYBNTRWJKQJDRE-UHFFFAOYSA-L 0.000 description 1
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- MUTGBJKUEZFXGO-UHFFFAOYSA-N hexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21 MUTGBJKUEZFXGO-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
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- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
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- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
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- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
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- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- ZYMLPCYLTMMPQE-UHFFFAOYSA-J tris(2,2-diethylhexanoyloxy)stannyl 2,2-diethylhexanoate Chemical compound [Sn+4].CCCCC(CC)(CC)C([O-])=O.CCCCC(CC)(CC)C([O-])=O.CCCCC(CC)(CC)C([O-])=O.CCCCC(CC)(CC)C([O-])=O ZYMLPCYLTMMPQE-UHFFFAOYSA-J 0.000 description 1
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- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
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Abstract
Description
(A)(i)少なくとも2つのイソシアネート基を含む1つ以上のイソシアネート化合物と、(ii)少なくとも2つのイソシアネート反応性基と式Iによって表される少なくとも1つの側鎖とを有する1つ以上の第1のイソシアネート反応性化合物、および(iii)少なくとも2つのイソシアネート反応性基を有し、式Iによって表される側鎖を有さない1つ以上の第2のイソシアネート反応性化合物との反応から誘導されるプレポリマーを含むイソシアネート成分であって、
-R2-(O-R1-O)n-R3式I
式中、R1はC2~C4アルキレン基を表し、R2はC1~C6アルキレン基であり、R3はC1~C6アルキルであり、nは8~25の整数であり、
プレポリマーが、少なくとも2つの遊離イソシアネート基を含む、イソシアネート成分と
(B)少なくとも2つのイソシアネート反応性基を有する1つ以上の第3のイソシアネート反応性化合物を含むイソシアネート反応性成分であって、第3のイソシアネート反応性化合物が、第1のイソシアネート反応性化合物とは異なる、イソシアネート反応性成分と、を含む無溶媒接着剤組成物を提供する。(B)イソシアネート反応性成分は、任意選択で、第1のイソシアネート反応性化合物と同一である第4のイソシアネート反応性化合物を含み得る。
-R2-(O-R1-O)n-R3式I
式中、R1はC2~C4アルキレン基を表し、R2はC1~C6アルキレン基であり、R3はC1~C6アルキルであり、nは8~25の整数であり、プレポリマーは、少なくとも2つの遊離イソシアネート基を含む。
結合強度(BS)
接着剤組成物、PET基材、およびPE60基材で調製したラミネートを、Instron Corporationから入手可能な5940 Series Single Column Table Top Systemを使用する250mm/分のクロスヘッド速度下でのT-剥離試験のために、15mm幅のストリップに切断した。試験中、各ストリップのテールを指で僅かに引っ張って、テールが剥離方向に対して90度のままであることを確認した。各サンプルの3つのストリップを試験し、平均値を計算した。結果をN/15mmの単位で表した。値が高いほど、より良好な結合強度を表す。
接着剤組成物、PET基材、およびPE60基材で調製したラミネートを、Brugger Companyから入手可能なHSG-C熱密封機で、140℃の密封温度および300Nの圧力で1秒間熱密封し、次いで冷却し、Instron Corporationから入手可能な5940 Series Single Column Table Top Systemを使用する250mm/分のクロスヘッド速度下での熱密封強度試験のために、15mm幅のストリップに切断した。各サンプルの3つのストリップを試験し、平均値を計算した。結果をN/15mmの単位で表した。値が高いほど、より良好な熱密封強度を表す。
新たにラミネートされたフィルム(接着剤組成物、PET基材、およびPE25基材で調製)を45℃のオーブンで24時間加熱し、次いで取り出して冷却し、64mm×64mmおよび10cm×10cmのストリップに切断した。64mm×64mmのストリップをスライダーに貼り付け、10cm×10cmのストリップを機械のプラットフォームに貼り付け、2つのストリップのPE側が向かい合っていることを確認して、摩擦値を提供した。COF機を試験前に較正した。各サンプルについて3つのストリップを試験し、平均値を計算した。
PETインク/MPETラミネートの光学的外観を視覚的に評価した。印刷されたPETフィルム上を接着剤で被覆し、MPETフィルムを接着剤層上に適用し、次いでラミネートを40oCで一晩硬化した。ラミネートの光学的外観を視覚的にチェックし、以下の基準に従って評価した。
良好:オレンジ色の剥離、泡、白い斑点、およびしわが観察されない。
不良:多くの欠陥、例えば、泡、白い斑点、しわ、オレンジ色の剥離が視覚的に観察できる。
Claims (9)
- 無溶媒接着剤組成物であって、
(A)(i)少なくとも2つのイソシアネート基を含む1つ以上のイソシアネート化合物と、(ii)少なくとも2つのイソシアネート反応性基と式Iによって表される少なくとも1つの側鎖とを有する1つ以上の第1のイソシアネート反応性化合物、および(iii)少なくとも2つのイソシアネート反応性基を有し、式Iによって表される側鎖を有さない1つ以上の第2のイソシアネート反応性化合物との反応から誘導されるプレポリマーを含むイソシアネート成分であって、
-R2-(O-R1-O)n-R3式I
式中、R1がC2~C4アルキレン基を表し、R2がC1~C6アルキレン基であり、R3がC1~C6アルキルであり、nが8~25の整数であり、
前記プレポリマーが、少なくとも2つの遊離イソシアネート基を含む、イソシアネート成分と
(B)少なくとも2つのイソシアネート反応性基を有する1つ以上の第3のイソシアネート反応性化合物を含むイソシアネート反応性成分であって、前記第3のイソシアネート反応性化合物が、前記第1のイソシアネート反応性化合物とは異なる、イソシアネート反応性成分と、を含む、無溶媒接着剤組成物。 - 少なくとも2つのイソシアネート基を有する前記1つ以上のイソシアネート化合物が、少なくとも2つのイソシアネート基を含むC4~C12脂肪族ポリイソシアネート、少なくとも2つのイソシアネート基を含むC6~C15脂環式または芳香族ポリイソシアネート、少なくとも2つのイソシアネート基を含むC7~C15アラリファティックポリイソシアネート、カルボジイミド変性イソシアネート、およびそれらの組み合わせからなる群から選択される、請求項1に記載の無溶媒接着剤組成物。
- 前記第1のイソシアネート反応性化合物が、式Iによって表される側鎖を有するポリオールである、請求項1に記載の無溶媒接着剤組成物。
- 前記第1のイソシアネート反応性化合物の含有量が、6重量%~20重量%であり、前記イソシアネート化合物、前記第1のイソシアネート反応性化合物、および前記第2のイソシアネート反応性化合物の組み合わせた重量が、100重量%と見なされる、請求項1に記載の無溶媒接着剤組成物。
- 前記第2のイソシアネート反応性化合物および前記第3のイソシアネート反応性化合物が独立して、500~5000g/molの分子量を有するポリエステルポリオール、200~5,000g/molの分子量を有するポリカーボネートポリオール、200~5,000g/molの分子量を有するポリエーテルポリオール、前記ポリエステルポリオールとポリエーテルポリオールとのブレンド、およびそれらの組み合わせからなる群から選択される、請求項1に記載の無溶媒接着剤組成物。
- 前記(B)イソシアネート反応性成分が、任意選択で、前記第1のイソシアネート反応性化合物と同一である第4のイソシアネート反応性化合物を含む、請求項1に記載の無溶媒接着剤組成物。
- 少なくとも2つの基材と、それらの間に挟まれた接着剤層とを備えるラミネート製品であって、前記接着剤層が、請求項1~7のいずれかに記載の無溶媒接着剤組成物の前記(A)イソシアネート成分と前記(B)イソシアネート反応性成分との間の反応によって形成される、ラミネート製品。
- 請求項8に記載のラミネート製品を調製するための方法であって、
請求項1~7のいずれかに記載の無溶媒接着剤組成物を提供するステップと、
前記無溶媒接着剤組成物を第1の基材の表面上に適用して、接着剤層を形成するステップと、
第2の基材を前記第1の基材の反対側の前記接着剤層の表面上に適用して、ラミネートを形成するステップと、
ラミネート全体を硬化させるステップと、を含む、方法。
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WO2020199175A1 (en) | 2020-10-08 |
AR118454A1 (es) | 2021-10-06 |
CN113748182A (zh) | 2021-12-03 |
MX2021012181A (es) | 2022-01-06 |
TW202104507A (zh) | 2021-02-01 |
US20220186097A1 (en) | 2022-06-16 |
EP3947588A1 (en) | 2022-02-09 |
EP3947588A4 (en) | 2022-10-26 |
JP7494221B2 (ja) | 2024-06-03 |
BR112021019940A2 (pt) | 2021-12-07 |
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