JP7404364B2 - 接着剤組成物 - Google Patents
接着剤組成物 Download PDFInfo
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- JP7404364B2 JP7404364B2 JP2021529352A JP2021529352A JP7404364B2 JP 7404364 B2 JP7404364 B2 JP 7404364B2 JP 2021529352 A JP2021529352 A JP 2021529352A JP 2021529352 A JP2021529352 A JP 2021529352A JP 7404364 B2 JP7404364 B2 JP 7404364B2
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- compound
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- 239000000853 adhesive Substances 0.000 title claims description 116
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical class CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- 239000005001 laminate film Substances 0.000 description 3
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- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 2
- WXUAQHNMJWJLTG-UHFFFAOYSA-N 2-methylbutanedioic acid Chemical compound OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-UHFFFAOYSA-N 0.000 description 2
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 2
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- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
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- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
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- 239000003880 polar aprotic solvent Substances 0.000 description 2
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- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- JIABEENURMZTTI-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatophenyl)methyl]benzene Chemical class O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O JIABEENURMZTTI-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- GOHPTLYPQCTZSE-UHFFFAOYSA-N 2,2-dimethylsuccinic acid Chemical compound OC(=O)C(C)(C)CC(O)=O GOHPTLYPQCTZSE-UHFFFAOYSA-N 0.000 description 1
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- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
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- 229910000831 Steel Inorganic materials 0.000 description 1
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- 230000000996 additive effect Effects 0.000 description 1
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- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
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- 239000001530 fumaric acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
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- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
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- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
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- 239000003586 protic polar solvent Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/06—Polyurethanes from polyesters
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
- B32B15/085—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin comprising polyolefins
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
- B32B15/088—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin comprising polyamides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
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Description
本発明の実施例および比較実施例で使用されるリン酸エステルポリオールは、表IIIの一覧にある配合物に従って合成される。原料の化合物PA115およびBester648を、1,000ミリリットル(mL)のガラス反応器に入れ、注意深く混合して配合物を形成する。すべての上記原料を供給した後、配合物の加熱を開始する。配合物が60℃付近になったら、回転速度を毎分50回転(RPM)に上げ、昇温速度を制御し、全プロセスを通じて反応を監視する。温度上昇プロセスの間、PA115はBester648から分離し、PA115は配合物の底部で濃縮する。一方、PA115の色も暗くなる。反応温度が約100~103℃までに達すると、反応生成物は透明で均一になる。反応生成物を、約100~103℃で2時間維持する。配合物のヒドロキシル価が理論値に達すると、反応器を可能な限り早く冷却する。反応器を、60℃~70℃まで冷却される。次に、最終生成物を、配合物を汚染から保護するために、窒素雰囲気にある十分に密封されたスチールボトルに充填する。
本発明の実施例および比較実施例を調製するために、イソシアネート成分およびポリオール成分は、表Vに示す組み合わせ(サンプル指定として)および混合比に従って混合して、実施例の接着剤組成物を形成する。次に、実施例の接着剤組成物を使用して、ナイロンフィルムおよび事前積層されたアルミニウム(Al)箔(すなわち、Al箔/RCPP積層体)を含む積層体を形成する。
実施例で使用されるコーティングおよび積層プロセスは、Nordmeccanica groupから入手可能なLabo-Combi400積層機で実行される。接着剤はナイロンフィルム上に塗布され、次いで、ナイロンフィルム/接着剤は事前積層されたAl箔/RCPPのアルミ箔表面に積層される。積層機のニップロールの温度は70℃に保たれ、塗布速度は積層プロセス中100メートル/分(m/min)である。ドライコーティング量は、4~4.5グラム/平方メートル(g/m2)に制御される。次いで、得られた積層フィルムを、試験前にオーブン中で硬化させる(例えば、60℃の温度で)。
ナイロン層と箔層との間の120℃でのT-剥離(90°)結合強度(手動アシストT-剥離)
硬化後、積層フィルムは、250ミリメートル/分(mm/分)のクロスヘッド速度を有するInstron5965U5974機でT-剥離試験用のための15mm幅の試験片サンプルに切断される。次に、3つの試験片を120℃の温かいオーブンで試験し、試験した3つの試験片の平均値を記録する。試験中、小片の尾部は、小片の尾部が剥離方向に向かって90°の状態を確実に維持するために、指によってわずかに引っ張られる。結合強度試験の結果は、N/15mmの単位で測定される。この結合強度試験に合格するためには、積層フィルムの結合強度は>2N/15mmであるべきである。
積層体(積層フィルム)を4cm×4cmサイズの正方形試験サンプルに切断し、次いでサンプルにエージング耐性試験を受けさせる。サンプルは、60時間の間、85℃および85%の相対空気湿度下で、恒温湿潤チャンバーのLHU-213中でエージングさせる。エージング耐性試験の間、1つの積層フィルムの中で6つの片を評価のために選択する。積層体のすべての片を周囲空気と完全に接触させる。エージング耐性試験後、最終的な積層フィルムの外観を評価する。エージング耐性試験に合格するためには、フィルム中に気泡が観察されるべきではなく、かつ積層フィルムの剥離が検出されるべきではない。
硬化した積層フィルムは、8cm×12cmサイズの矩形試験サンプルに切断され、次いで、サンプルを、評価のために、自動深絞り装置(SDCK-004A)のプラットフォームに配置する。装置は空気圧を0.5メガパスカル(MPa)に調整し、モールドのパンチ速度を100mm/分に維持する深絞り用途用の特定パラメータで操作される。深絞り成形の深さは、試験したすべての積層体に対して5mmに設定される。深絞り成形の際に、積層体の表面のナイロン側は、外層として凸面を形成する。異なる接着剤が積層体に使用される。深絞り成形後の積層体の外観は、気泡、トンネル、および/または剥離について視覚的に検査される。また、積層体は、破壊された基材のいかなる兆候についても検査される。一方、パンチ後の積層体も温かいオーブンで100℃まで1時間加熱し、その後、積層体の外観は、上記のように欠陥に対して視覚的に再度検査される。
(1)ポリウレタン接着剤組成物であって、(A)少なくとも1つのイソシアネート基含有化合物を含む少なくとも1つのイソシアネート基含有成分と、(B)少なくとも1つのポリオール成分と、を含み、少なくとも1つのポリオール成分(B)が、(Bi)>8,000g/molの分子量(Mn)を有する少なくとも1つのポリエステルポリオール化合物、および(Bii)少なくとも1つのリン酸エステルポリオール化合物を含む、組成物。
(I)少なくとも第1の基材の1つの表面の少なくとも一部分、または少なくとも第2の基材の1つの表面の少なくとも一部分を、実施形態(1)の接着剤組成物と接触させることと、(II)結合された第1の基材、第2の基材、および工程(I)の接着剤を、接着剤組成物を硬化させるのに十分な温度まで加熱することと、を含む、プロセス。
本願発明には以下の態様が含まれる。
項1.
ポリウレタン接着剤組成物であって、
(A)少なくとも1つのイソシアネート基含有化合物を含む、少なくとも1つのイソシアネート基含有成分と、
(B)
(Bi)8,000グラム/モルを超える分子量(Mn)を有する、少なくとも1つのポリエステルポリオール化合物と、
(Bii)少なくとも1つのリン酸エステルポリオール化合物と、を含む、少なくとも1つのポリオール成分と、を含む、組成物。
項2.
成分(B)と成分(A)との乾燥重量による濃度比[B:A]は、1~20である、項1に記載の組成物。
項3.
前記ポリウレタン接着剤組成物は、(i)1N/15mm~8N/15mmの結合強度を有し、(ii)85℃および85%の湿度で60時間を超えるエージング時間に合格し、および/または(iii)1ミリメートル~15ミリメートルの深絞り設定の深さを提供するのに十分な成形性を有する、項1に記載の組成物。
項4.
前記少なくとも1つのリン酸エステルポリオール化合物の成分である成分(Bii)は、以下の構造(I)または構造(II)を有する化合物であり、
項5.
前記少なくとも1つのリン酸エステルポリオール化合物である成分(Bii)は、(a)ポリエーテルポリオール、ポリエステルポリオール、またはこれらの混合物と、(b)ポリリン酸、またはポリリン酸と他の酸との混合物と、の反応生成物である、項1に記載の組成物。
項6.
ポリウレタン接着剤組成物を作製するためのプロセスであって、
(A)少なくとも1つのイソシアネート基含有化合物を含む、少なくとも1つのイソシアネート基含有成分と、
(B)
(Bi)少なくとも1つのポリエステルポリオール化合物と、
(Bii)少なくとも1つのリン酸エステルポリオール化合物と、を含む、少なくとも1つのポリオール成分と、を混和することを含む、プロセス。
項7.
少なくとも第1の基材および少なくとも第2の基材を接着するためのプロセスであって、
(I)前記少なくとも第1の基材の1つの表面の少なくとも一部分、または前記少なくとも第2の基材の1つの表面の少なくとも一部分を、項1に記載の接着剤組成物と接触させることと、
(II)工程(I)の前記組み合わされた第1の基材、第2の基材、および前記接着剤を、前記接着剤組成物を硬化させるのに十分な温度まで加熱することと、を含む、プロセス。
項8.
前記加熱工程(II)は、25℃~80℃の温度で実施される、項7に記載の方法。
項9.
項8に記載のプロセスによって作製される、多層複合積層フィルム構造体。
項10.
箔ベースの積層構造体を含むリチウムイオン電池を包装するためのパッケージであって、前記箔ベースの積層構造体は、(a)ナイロン層と、(b)箔層と、(c)ポリマー基材層と、(d)前記ナイロン層の一方の側と前記箔層の一方の側との間に配置された項1に記載の組成物を含む第1の上部接着剤層と、(e)前記箔層の他方の側と前記ポリマー基材層の一方の側との間に配置された項1に記載の組成物とは異なる第2の下部接着剤層と、の組み合わせを含む、パッケージ。
Claims (6)
- ポリウレタン接着剤組成物であって、
(A)少なくとも1つのイソシアネート基含有化合物を含む、少なくとも1つのイソシアネート基含有成分と、
(B)
(Bi)8,000グラム/モルを超える分子量(Mn)を有する、少なくとも1つのポリエステルポリオール化合物と、
(Bii)少なくとも1つのリン酸エステルポリオール化合物と、を含む、少なくとも1つのポリオール成分と、を含み、
前記リン酸エステルポリオール化合物は、前記ポリオール成分中に0.3重量%から2重量%の量で存在する、組成物。 - 成分(B)と成分(A)との乾燥重量による濃度比[B/A]は、1~20である、請求項1に記載の組成物。
- 前記ポリウレタン接着剤組成物は、(i)1N/15mm~8N/15mmの結合強度を有し、(ii)85℃および85%の湿度で60時間を超えるエージング時間に合格し、および/または(iii)1ミリメートル~15ミリメートルの深絞り設定の深さを提供するのに十分な成形性を有する、請求項1に記載の組成物。
- 前記少なくとも1つのリン酸エステルポリオール化合物の成分である成分(Bii)は、以下の構造(I)または構造(II)を有する化合物であり、
- 前記少なくとも1つのリン酸エステルポリオール化合物である成分(Bii)は、(a)ポリエーテルポリオール、ポリエステルポリオール、またはこれらの混合物と、(b)ポリリン酸、またはポリリン酸と他の酸との混合物と、の反応生成物である、請求項1に記載の組成物。
- 箔ベースの積層構造体を含むリチウムイオン電池を包装するためのパッケージであって、前記箔ベースの積層構造体は、(a)ナイロン層と、(b)箔層と、(c)ポリマー基材層と、(d)前記ナイロン層の一方の側と前記箔層の一方の側との間に配置された請求項1に記載の組成物を含む第1の上部接着剤層と、(e)前記箔層の他方の側と前記ポリマー基材層の一方の側との間に配置された請求項1に記載の組成物とは異なる第2の下部接着剤層と、の組み合わせを含む、パッケージ。
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