JP2022535493A - 接着剤組成物 - Google Patents
接着剤組成物 Download PDFInfo
- Publication number
- JP2022535493A JP2022535493A JP2021562036A JP2021562036A JP2022535493A JP 2022535493 A JP2022535493 A JP 2022535493A JP 2021562036 A JP2021562036 A JP 2021562036A JP 2021562036 A JP2021562036 A JP 2021562036A JP 2022535493 A JP2022535493 A JP 2022535493A
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- JP
- Japan
- Prior art keywords
- adhesive composition
- catalyst
- adhesive
- crystalline
- component
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000000203 mixture Substances 0.000 title claims abstract description 109
- 239000000853 adhesive Substances 0.000 title claims abstract description 108
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 108
- 239000003054 catalyst Substances 0.000 claims abstract description 77
- 229920005862 polyol Polymers 0.000 claims abstract description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- -1 polyol compound Chemical class 0.000 claims abstract description 17
- 239000012948 isocyanate Substances 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 12
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 11
- 239000011541 reaction mixture Substances 0.000 claims abstract description 4
- 239000000758 substrate Substances 0.000 claims description 15
- 239000000178 monomer Substances 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000012360 testing method Methods 0.000 claims description 6
- 238000007334 copolymerization reaction Methods 0.000 claims description 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
- 239000003999 initiator Substances 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 4
- 230000008018 melting Effects 0.000 claims description 4
- 239000012986 chain transfer agent Substances 0.000 claims description 3
- FSAJWMJJORKPKS-UHFFFAOYSA-N octadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C=C FSAJWMJJORKPKS-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- OCDWICPYKQMQSQ-UHFFFAOYSA-N docosyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCOC(=O)C(C)=C OCDWICPYKQMQSQ-UHFFFAOYSA-N 0.000 claims 1
- KHAYCTOSKLIHEP-UHFFFAOYSA-N docosyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCOC(=O)C=C KHAYCTOSKLIHEP-UHFFFAOYSA-N 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 claims 1
- 150000003077 polyols Chemical class 0.000 description 32
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 15
- 239000004814 polyurethane Substances 0.000 description 15
- 229920002635 polyurethane Polymers 0.000 description 14
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 229920005906 polyester polyol Polymers 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
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- 239000000654 additive Substances 0.000 description 5
- 229920001228 polyisocyanate Polymers 0.000 description 5
- 239000005056 polyisocyanate Substances 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 4
- 235000011037 adipic acid Nutrition 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 229920000909 polytetrahydrofuran Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
- 239000004970 Chain extender Substances 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229920001748 polybutylene Polymers 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- 150000003628 tricarboxylic acids Chemical class 0.000 description 2
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000005007 epoxy-phenolic resin Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012939 laminating adhesive Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
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- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 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
- 239000013557 residual solvent Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
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- B32B7/04—Interconnection of layers
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- 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
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- C08G18/08—Processes
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- B32B2255/00—Coating on the layer surface
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Abstract
Description
共重合結晶性触媒を、以下のプロセスに従ってトルエン溶液中で調製した。結晶性アクリレートモノマー、DBTM、開始剤AIBN、鎖延長剤、およびトルエンを、緩徐に撹拌しながら合わせて混合した。次に、得られた混合物の温度を、撹拌を継続しながら60℃~80℃の温度に上昇させ、混合物の温度を60℃~80℃に24時間維持した。その後、混合物の撹拌を停止し、冷却した。得られたコポリマーをメタノールに沈殿させ、沈殿物を40℃の真空オーブンに24時間入れて、あらゆる残留溶媒を除去した。最終共重合触媒は、上記の除去ステップの後に得られた。
塗布性能評価 共重合結晶性触媒を用いた2K無溶剤(SL)PU接着剤
表IIに記載する4つの共重合結晶性触媒の各々を、2成分(2k)無溶剤(SL)ポリウレタン(PU)接着剤組成物に加えて、本発明の接着剤組成物を形成し、本接着剤組成物の性能を評価した。本接着剤組成物の可使時間および接着強度増進の性能を評価した。それぞれ、表IIに記載の共重合結晶性触媒Cat.1~4を含有する本発明の接着剤組成物、発明実施例1~4の性能結果(可使時間および接着強度増進)を、(1)共重合結晶性触媒の非存在下の2k SL PU接着剤組成物(比較例A)、および(2)共重合されていない結晶性触媒である純DBTMを含有する2k SL PU接着剤組成物(比較例B)と比較し、性能結果を表IIIに記載する。
Claims (12)
- 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含有化合物と、
(B)少なくとも1つのポリオール化合物と、
(C)少なくとも1つの共重合結晶性潜伏性触媒と、の反応混合物を含む、接着剤組成物。 - 成分(C)の前記少なくとも1つの共重合結晶性潜伏性触媒が、(a)少なくとも1つの結晶性アクリレートモノマーと、(b)少なくとも1つの共重合性触媒化合物と、(c)少なくとも1つの開始剤と、(d)少なくとも1つの連鎖移動剤と、(e)任意選択で、少なくとも1つの溶剤と、の反応生成物を含む、請求項1に記載の接着剤組成物。
- 前記接着剤組成物が、30℃から40℃の温度での前記接着剤組成物の粘度変化を追跡し、前記接着剤組成物が3,000ミリパスカル秒の粘度に到達するまでにかかる時間を記録することにより測定して、成分(C)の前記共重合結晶性潜伏性触媒を含まない接着剤組成物と比較して、少なくとも類似した可使時間を有する、請求項1に記載の接着剤組成物。
- 前記接着剤組成物が、T剥離試験により測定して、成分(C)の前記共重合結晶性潜伏性触媒を含まない接着剤組成物と比較して、より速い接着強度の増進を有する、請求項1に記載の接着剤組成物。
- 前記共重合結晶性潜伏性触媒の前記結晶性アクリレートモノマーが、アクリル酸オクタデシル、メタクリル酸オクタデシル、アクリル酸ドコシル、メタクリル酸ドコシル、およびそれらの混合物からなる群から選択され、前記共重合結晶性潜伏性触媒の前記共重合性触媒化合物が、スズ含有触媒化合物である、請求項2に記載の接着剤組成物。
- 成分(A)の前記少なくとも1つのイソシアネート含有化合物の濃度が10重量パーセント~78重量パーセントである、請求項1に記載の接着剤組成物。
- 成分(B)の前記少なくとも1つのポリオール化合物の濃度が20重量パーセント~88重量パーセントである、請求項1に記載の接着剤組成物。
- 成分(C)の前記少なくとも1つの共重合結晶性潜伏性触媒化合物の濃度が0.01重量パーセント~10重量パーセントである、請求項1に記載の接着剤組成物。
- 前記共重合結晶性潜伏性触媒の融点が45℃~60℃であり、前記共重合結晶性潜伏性触媒の結晶温度が40℃~55℃である、請求項1に記載の接着剤組成物。
- 接着剤組成物を作製するプロセスであって、
(A)少なくとも1つのイソシアネート含有化合物と、
(B)少なくとも1つのポリオール化合物と、
(C)共重合結晶性潜伏性触媒と、を混合することを含む、プロセス。 - 積層構造を作製するためのプロセスであって、
(I)少なくとも第1の基材および少なくとも第2の基材を提供するステップと、
(II)請求項1に記載の接着剤組成物を、前記少なくとも第1の基材または前記少なくとも第2の基材の片面の少なくとも一部分に塗布して、前記第1または第2の基材上に配置された接着剤のフィルム層を形成するステップと、
(III)前記第1および第2の基材を、前記第1の基材と前記第2の基材との間に配置される前記接着剤と接触させて、層状積層構造を形成するステップと、
(IV)前記層状積層構造を加熱して、前記接着剤を硬化させ、その結果、接着積層構造が形成されるようにするステップと、を含む、プロセス。 - 請求項11に記載のプロセスによって作製された、積層構造。
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