WO2023032690A1 - 接着剤、積層体、積層体の製造方法、包装材 - Google Patents
接着剤、積層体、積層体の製造方法、包装材 Download PDFInfo
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- WO2023032690A1 WO2023032690A1 PCT/JP2022/031160 JP2022031160W WO2023032690A1 WO 2023032690 A1 WO2023032690 A1 WO 2023032690A1 JP 2022031160 W JP2022031160 W JP 2022031160W WO 2023032690 A1 WO2023032690 A1 WO 2023032690A1
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- WIPO (PCT)
- Prior art keywords
- polyol
- acid
- composition
- adhesive
- polyisocyanate
- Prior art date
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- 239000000853 adhesive Substances 0.000 title claims abstract description 59
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 59
- 239000005022 packaging material Substances 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 title description 24
- 238000004519 manufacturing process Methods 0.000 title description 5
- 239000002648 laminated material Substances 0.000 title 1
- 150000003077 polyols Chemical class 0.000 claims abstract description 120
- 229920005862 polyol Polymers 0.000 claims abstract description 112
- 239000000203 mixture Substances 0.000 claims abstract description 90
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- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 64
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims abstract description 7
- JVYDLYGCSIHCMR-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butanoic acid Chemical compound CCC(CO)(CO)C(O)=O JVYDLYGCSIHCMR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000012790 adhesive layer Substances 0.000 claims description 44
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- 239000000463 material Substances 0.000 claims description 28
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- 239000003054 catalyst Substances 0.000 claims description 18
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- 150000005846 sugar alcohols Polymers 0.000 claims description 5
- UHAMPPWFPNXLIU-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)pentanoic acid Chemical compound CCCC(CO)(CO)C(O)=O UHAMPPWFPNXLIU-UHFFFAOYSA-N 0.000 claims description 2
- ULMZOZMSDIOZAF-UHFFFAOYSA-N 3-hydroxy-2-(hydroxymethyl)propanoic acid Chemical compound OCC(CO)C(O)=O ULMZOZMSDIOZAF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 abstract description 30
- 239000002184 metal Substances 0.000 abstract description 30
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- 238000001465 metallisation Methods 0.000 abstract description 5
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- -1 polymethylene Polymers 0.000 description 60
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- 239000010410 layer Substances 0.000 description 30
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- 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 10
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 9
- 239000012948 isocyanate Substances 0.000 description 9
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- 238000007789 sealing Methods 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
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- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
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- 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 7
- 239000000976 ink Substances 0.000 description 7
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- 239000000377 silicon dioxide Substances 0.000 description 7
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
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- 229930195729 fatty acid Natural products 0.000 description 6
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-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
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
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- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
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- 239000012744 reinforcing agent Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 239000012603 secondary packaging material Substances 0.000 description 1
- 150000003346 selenoethers Chemical class 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- QXKXDIKCIPXUPL-UHFFFAOYSA-N sulfanylidenemercury Chemical compound [Hg]=S QXKXDIKCIPXUPL-UHFFFAOYSA-N 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- PZTAGFCBNDBBFZ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CO PZTAGFCBNDBBFZ-UHFFFAOYSA-N 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
- GNCDUZFXTFAOBE-UHFFFAOYSA-N tetrakis(2-ethylhexyl) benzene-1,2,4,5-tetracarboxylate Chemical compound CCCCC(CC)COC(=O)C1=CC(C(=O)OCC(CC)CCCC)=C(C(=O)OCC(CC)CCCC)C=C1C(=O)OCC(CC)CCCC GNCDUZFXTFAOBE-UHFFFAOYSA-N 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 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 1
- 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
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- WEAPVABOECTMGR-UHFFFAOYSA-N triethyl 2-acetyloxypropane-1,2,3-tricarboxylate Chemical compound CCOC(=O)CC(C(=O)OCC)(OC(C)=O)CC(=O)OCC WEAPVABOECTMGR-UHFFFAOYSA-N 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- MXHBQKVKHGQWRB-UHFFFAOYSA-N trihexyl benzene-1,2,4-tricarboxylate Chemical compound CCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCC)C(C(=O)OCCCCCC)=C1 MXHBQKVKHGQWRB-UHFFFAOYSA-N 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- JNXDCMUUZNIWPQ-UHFFFAOYSA-N trioctyl benzene-1,2,4-tricarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC)C(C(=O)OCCCCCCCC)=C1 JNXDCMUUZNIWPQ-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- KOWVWXQNQNCRRS-UHFFFAOYSA-N tris(2,4-dimethylphenyl) phosphate Chemical compound CC1=CC(C)=CC=C1OP(=O)(OC=1C(=CC(C)=CC=1)C)OC1=CC=C(C)C=C1C KOWVWXQNQNCRRS-UHFFFAOYSA-N 0.000 description 1
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
- DUHIKWRPAQIIBL-UHFFFAOYSA-N tris(2-ethylhexyl) 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CCCCC(CC)COC(=O)CC(O)(C(=O)OCC(CC)CCCC)CC(=O)OCC(CC)CCCC DUHIKWRPAQIIBL-UHFFFAOYSA-N 0.000 description 1
- LIPMRGQQBZJCTM-UHFFFAOYSA-N tris(2-propan-2-ylphenyl) phosphate Chemical compound CC(C)C1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C(C)C)OC1=CC=CC=C1C(C)C LIPMRGQQBZJCTM-UHFFFAOYSA-N 0.000 description 1
- WDRCVXGINNJWPH-UHFFFAOYSA-N tris(6-methylheptyl) benzene-1,2,4-tricarboxylate Chemical compound CC(C)CCCCCOC(=O)C1=CC=C(C(=O)OCCCCCC(C)C)C(C(=O)OCCCCCC(C)C)=C1 WDRCVXGINNJWPH-UHFFFAOYSA-N 0.000 description 1
- FJFYFBRNDHRTHL-UHFFFAOYSA-N tris(8-methylnonyl) benzene-1,2,4-tricarboxylate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC(C)C)C(C(=O)OCCCCCCCC(C)C)=C1 FJFYFBRNDHRTHL-UHFFFAOYSA-N 0.000 description 1
- SMYKBXMWXCZOLU-UHFFFAOYSA-N tris-decyl benzene-1,2,4-tricarboxylate Chemical compound CCCCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCCCC)C(C(=O)OCCCCCCCCCC)=C1 SMYKBXMWXCZOLU-UHFFFAOYSA-N 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
- JBCJMTUHAXHILC-UHFFFAOYSA-N zinc;octanoic acid Chemical compound [Zn+2].CCCCCCCC(O)=O JBCJMTUHAXHILC-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- 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
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/40—Layered products comprising a layer of synthetic resin comprising polyurethanes
-
- 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
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/04—Interconnection of layers
- B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D65/00—Wrappers or flexible covers; Packaging materials of special type or form
- B65D65/38—Packaging materials of special type or form
- B65D65/40—Applications of laminates for particular packaging purposes
-
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- 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
-
- 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
-
- 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
- C09J175/08—Polyurethanes from polyethers
-
- 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
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
- C09J5/04—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving separate application of adhesive ingredients to the different surfaces to be joined
Definitions
- the present invention relates to an adhesive, a laminate obtained using the adhesive, a method for producing the laminate, and a packaging material.
- Laminates used for various packaging materials, labels, etc. are given design, functionality, storage stability, convenience, transportation resistance, etc. by laminating a wide variety of base materials such as plastic films, metal foils, and paper. be done.
- a packaging material formed by molding the laminate into a bag shape is used as a packaging material for foods, medicines, detergents, and the like.
- laminates used for packaging materials are produced by applying an adhesive dissolved in a volatile organic solvent (sometimes referred to as a solvent-based lamination adhesive) to the base material, and then passing through an oven.
- a volatile organic solvent sometimes referred to as a solvent-based lamination adhesive
- reaction lamination methods that do not contain volatile organic solvents have been used.
- Demand for a two-liquid type lamination adhesive (hereinafter referred to as a non-solvent adhesive) is increasing (Patent Document 1).
- Solvent-free adhesives do not require a drying process and do not emit solvents. They are energy-saving and have low running costs. It has many merits, such as the fact that there is no concern that the solvent will remain in the laminate after being combined. On the other hand, the components used in solvent-free adhesives must be designed to have a low molecular weight so that they have a viscosity that allows coating when heated to about 40°C to 100°C. The adhesion of was insufficient.
- the present invention has been made in view of such circumstances, and a two-component curing adhesive that has excellent adhesion to metal foils and metal vapor deposition layers even when the molecular weight is low, and is obtained by using the adhesive.
- An object of the present invention is to provide a laminated body and a packaging material.
- the present invention comprises a polyisocyanate composition (X) and a polyol composition (Y), the polyisocyanate composition (X) comprising a polyisocyanate compound (A), and the polyol composition (Y) comprising a polyol ( B) and a compound (C) which is at least one compound selected from the group consisting of dimethylolpropionic acid and dimethylolbutanoic acid.
- the adhesive of the present invention is a two-component curing type containing a polyisocyanate composition (X) and a polyol composition (Y).
- the adhesive of the present invention will be described in detail below.
- the polyisocyanate composition (X) contains a polyisocyanate compound (A) having multiple isocyanate groups.
- the polyisocyanate compound (A) is not particularly limited, and includes aromatic diisocyanates, araliphatic diisocyanates, aliphatic diisocyanates, alicyclic diisocyanates, and burettes, nurates, adducts, allophanates, and carbodiimide modifications of these diisocyanates. , uretdione-modified products, urethane prepolymers obtained by reacting these polyisocyanates with polyols, and the like, and these can be used alone or in combination.
- aromatic diisocyanates examples include 2,2'-diphenylmethane diisocyanate, 2,4'-diphenylmethane diisocyanate, 4,4'-diphenylmethane diisocyanate, polymethylene polyphenyl polyisocyanate (also referred to as polymeric MDI or crude MDI).
- Araliphatic diisocyanate means an aliphatic isocyanate having one or more aromatic rings in the molecule, m- or p-xylylene diisocyanate (also known as XDI), ⁇ , ⁇ , ⁇ ', ⁇ '-tetra Methyl xylylene diisocyanate (another name: TMXDI) and the like can be mentioned, but not limited to these.
- Aliphatic diisocyanates include trimethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate (also known as HDI), pentamethylene diisocyanate, 1,2-propylene diisocyanate, 2,3-butylene diisocyanate, 1,3-butylene diisocyanate, and dodecamethylene. Examples include, but are not limited to, diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, and the like.
- Alicyclic diisocyanates include 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate, isophorone diisocyanate (also known as IPDI), 1,3-cyclopentane diisocyanate, 1,3-cyclohexane diisocyanate, 1,4-cyclohexane diisocyanate, methyl-2,4-cyclohexanediisocyanate, methyl-2,6-cyclohexanediisocyanate, 4,4′-methylenebis(cyclohexylisocyanate), 1,4-bis(isocyanatomethyl)cyclohexane, etc., and these is not limited to
- Polyols used for synthesis of urethane prepolymers include, for example, ethylene glycol, propylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 3-methyl-1,5-pentanediol, Alkylene glycols such as 1,6-hexanediol, neopentyl glycol, methylpentanediol, dimethylbutanediol, butylethylpropanediol, 1,4-cyclohexanediol, 1,4-cyclohexanedimethanol;
- Bisphenols such as bisphenol A, bisphenol F, hydrogenated bisphenol A, hydrogenated bisphenol F; dimer diall; bishydroxyethoxybenzene;
- Polyalkylene glycols such as diethylene glycol, triethylene glycol, other polyethylene glycols, polypropylene glycol, polybutylene glycol; Urethane bond-containing polyether polyol obtained by further polymerizing polyalkylene glycol with aromatic or aliphatic polyisocyanate;
- at least one aromatic polyvalent carboxylic acid such as aliphatic dicarboxylic acid, orthophthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, pyromellitic acid, etc. having 2 to 13 carbon atoms such as acid.
- polyester polyol obtained by; Polyester obtained by ring-opening polymerization reaction of cyclic ester compounds such as propiolactone, butyrolactone, ⁇ -caprolactone, ⁇ -valerolactone, ⁇ -methyl- ⁇ -valerolactone, glycol, glycerin, trimethylolpropane, pentaerythritol, etc. and a polyester polyol which is a reaction product with a polyhydric alcohol.
- cyclic ester compounds such as propiolactone, butyrolactone, ⁇ -caprolactone, ⁇ -valerolactone, ⁇ -methyl- ⁇ -valerolactone, glycol, glycerin, trimethylolpropane, pentaerythritol, etc.
- the polyisocyanate (a1-1) containing at least 4,4'-diphenylmethane diisocyanate as the polyisocyanate compound (A). It preferably contains a urethane prepolymer (A1) which is a reaction product of and polyol (a1-2).
- Polyisocyanate (a1-1) contains 4,4'-diphenylmethane diisocyanate, but may contain other polyisocyanate compounds.
- the polyisocyanate compound that can be used in combination with 4,4'-diphenylmethane diisocyanate is not particularly limited, and those exemplified as the polyisocyanate compound (A) can be used singly or in combination of two or more.
- the content of 4,4′-diphenylmethane diisocyanate in the polyisocyanate (a1-1) is preferably 40 to 99% by mass, preferably 75 to 90% by mass.
- polystyrene resin As the polyol (a1-2), the same ones as exemplified in the description of the polyisocyanate compound (A) can be used. At least one of polyalkylene glycol and polyester polyol is preferably used. Polyalkylene glycol and polyester polyol preferably have a number average molecular weight of 200 to 6,000. In the present invention, the weight average molecular weight (Mw) and number average molecular weight (Mn) are values measured by gel permeation chromatography (GPC) under the following conditions.
- HLC-8320GPC manufactured by Tosoh Corporation Column
- TSKgel 4000HXL TSKgel 3000HXL
- TSKgel 2000HXL TSKgel 1000HXL manufactured by Tosoh Corporation Detector
- RI differential refractometer
- Multi-station GPC-8020modelII manufactured by Tosoh Corporation Measurement conditions
- Monodisperse polystyrene Sample 0.2 mass% tetrahydrofuran solution in terms of resin solid content filtered through a microfilter (100 ⁇ l)
- the urethane prepolymer (A1) has an equivalent ratio [NCO]/[OH] between the isocyanate group of the polyisocyanate (a1-1) and the hydroxyl group of the polyol (a1-2) of 1.5 to 5.0. It is preferable that it is obtained by reacting within the range. Further, the urethane prepolymer (A1) preferably has an isocyanate content of 5 to 20% by mass by titration (using di-n-butylamine). This makes it possible to obtain an adhesive with excellent coatability.
- the polyisocyanate composition (X) may contain an isocyanate compound (A2) other than the urethane prepolymer (A1).
- an isocyanate compound (A2) those exemplified as the polyisocyanate compound (A) can be appropriately used.
- Carbodiimide-modified diisocyanate and polymethylene polyphenyl polyisocyanate also called polymeric MDI or crude MDI are preferred.
- the mixing ratio thereof is a mass ratio of the urethane prepolymer (A1), urethane prepolymer (A1) / isocyanate compound (A2) of 50/50 to It is preferably 99/1, more preferably 70/30 to 97/3.
- the polyol (B) used in the present invention is not particularly limited and includes ethylene glycol, propylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 3-methyl-1,5 - pentanediol, 1,6-hexanediol, neopentyl glycol, methylpentanediol, dimethylbutanediol, butylethylpropanediol, diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, tripropylene glycol, bishydroxyethoxybenzene , 1,4-cyclohexanediol, 1,4-cyclohexanedimethanol, triethylene glycol; trifunctional or tetrafunctional aliphatic alcohols such as glycerin, trimethylol
- Polyethers obtained by addition polymerization of alkylene oxides such as ethylene oxide, propylene oxide, butylene oxide, styrene oxide, epichlorohydrin, tetrahydrofuran, and cyclohexylene in the presence of polymerization initiators such as glycols and trifunctional or tetrafunctional aliphatic alcohols.
- alkylene oxides such as ethylene oxide, propylene oxide, butylene oxide, styrene oxide, epichlorohydrin, tetrahydrofuran, and cyclohexylene
- polymerization initiators such as glycols and trifunctional or tetrafunctional aliphatic alcohols.
- Polyesters obtained by ring-opening polymerization reaction of cyclic ester compounds such as propiolactone, butyrolactone, ⁇ -caprolactone, ⁇ -valerolactone, ⁇ -methyl- ⁇ -valerolactone, and the aforementioned glycols, glycerin, trimethylolpropane, pentaerythritol, etc.
- polyester polyol (1) which is a reaction product with a polyhydric alcohol
- a polyester polyol (2) obtained by reacting a bifunctional polyol such as the glycol, dimer diol, or bisphenol with a polyvalent carboxylic acid
- polyester polyol (3) obtained by reacting the trifunctional or tetrafunctional aliphatic alcohol with a polycarboxylic acid
- Polyester polyol (4) obtained by reacting a bifunctional polyol such as the glycol, dimer diol, or bisphenol, the trifunctional or tetrafunctional aliphatic alcohol, and a polyvalent carboxylic acid
- polyester polyols (5) which are polymers of hydroxyl acids such as dimethylolpropionic acid and castor oil fatty acids;
- Vegetable oil polyols such as castor oil, dehydrated castor oil, hydrogenated castor oil that is a hydrogenated castor oil, and alkylene oxide 5-50 mol adduct of castor oil;
- Polyurethane polyols, polyether polyurethane polyols, polyester polyurethane polyols, polyether polyester polyols, etc., which are reaction products of at least one of the above polyols and a polyisocyanate compound, may be used alone or in combination of two or more. can be done.
- the polyvalent carboxylic acid includes succinic acid, adipic acid, azelaic acid, sebacic acid, dodecanedicarboxylic acid, maleic anhydride, fumaric acid, 1,3-cyclopentanedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, and the like.
- Aliphatic dicarboxylic acids are included; orthophthalic acid, isophthalic acid, terephthalic acid, 1,4-naphthalenedicarboxylic acid, 2,5-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, naphthalic acid, biphenyldicarboxylic acid, 1,2-bis aromatic dicarboxylic acids such as (phenoxy)ethane-p,p'-dicarboxylic acid; and anhydrides or ester-forming derivatives of these aliphatic or dicarboxylic acids; p-hydroxybenzoic acid, p-(2-hydroxyethoxy)benzoic acid Acids, ester-forming derivatives of these dihydroxycarboxylic acids, and polybasic acids such as dimer acids are included.
- polyisocyanate compound the same ones as exemplified as the polyisocyanate compound (A) can be used.
- Polyol (B) preferably contains at least one of polyether polyol (B1) and vegetable oil polyol (B2), since the adhesive can be excellent in coatability even when heated at a relatively low temperature of about 40°C.
- the amount of polyether polyol (B1) or vegetable oil polyol (B2) in polyol (B) is preferably 20% by mass or more, more preferably 30% by mass. Although it may be 100% by mass, it is more preferably 80% by mass or less.
- the polyol (B) preferably contains a polyether diol (B1-1) having a number average molecular weight of 130 or more and 3000 or less.
- the adhesive layer can be given appropriate flexibility, and the laminate strength is improved.
- the polyol (B) contains the polyether polyol (B1-1) the blending amount in the polyol (B) is preferably 10% by mass or more and 50% by mass or less.
- the polyether polyol (B1-2) can be adjusted as appropriate, and is, for example, 450 or more and 1,000 or less.
- the blending amount in the polyol (B) is preferably 10% by mass or more and 30% by mass or less.
- the polyol (B) preferably contains a polyester polyol (B3). This makes it possible to improve the adhesiveness with hard films such as nylon films.
- polyester polyol (B3) those exemplified above can be used as appropriate, but even when heated at a relatively low temperature of about 40° C., an adhesive with excellent coatability can be obtained, and the polyether polyol (B1) It is preferable to use a reaction product of a composition containing an aliphatic polyol and an aliphatic polyhydric carboxylic acid because of its excellent compatibility with the polycarboxylic acid and the vegetable oil polyol (B2).
- the amount of the aliphatic polyol compounded is preferably 80% by mass or more, preferably 90% by mass or more, and preferably 95% by mass or more. .
- the total amount may be aliphatic polyol.
- the amount of the aliphatic polycarboxylic acid is preferably 80% by mass or more, preferably 90% by mass or more, and 95% by mass. It is preferable that it is above.
- Aliphatic polyhydric carboxylic acid may be sufficient as the whole quantity of polyhydric carboxylic acid.
- the blending amount of the polyester polyol (B3) in the polyol (B) is preferably 5% by mass or more and 50% by mass or less, and preferably 20% by mass or more and 30% by mass, from the viewpoint of the balance between the adhesion to the hard film and the seal strength. % or less.
- Compound (C) used in the present invention is selected from the group consisting of 2,2-dimethylolacetic acid, 2,2-dimethylolpropionic acid, 2,2-dimethylolbutanoic acid, and 2,2-dimethylolpentanoic acid. It preferably contains at least one of 2,2-dimethylolpropionic acid and 2,2-dimethylolbutanoic acid, and more preferably contains 2,2-dimethylolpropionic acid.
- an adhesive having excellent adhesion to metal substrates and pot life can be obtained.
- the compounding amount of the compound (C) in the polyol composition (Y) is preferably 0.1% by mass or more, and is 0.5% by mass or more. is more preferable.
- the compounding amount of compound (C) is preferably 10% by mass or less, more preferably 2.5% by mass or less.
- the polyol composition (Y) preferably contains a polyamine (D) having multiple amino groups.
- an amino group refers to an NH2 group or an NHR group (R is an optionally functionalized alkyl group or aryl group).
- polyamine (D) known ones can be used without particular limitation, such as methylenediamine, ethylenediamine, isophoronediamine, 3,9-dipropanamine-2,4,8,10-tetraoxapyrodundecane, lysine, Phenylenediamine, 2,2,4-trimethylhexamethylenediamine, tolylenediamine, hydrazine, piperazine, hexamethylenediamine, propylenediamine, dicyclohexylmethane-4,4-diamine, 2-hydroxyethylethylenediamine, di-2-hydroxyethyl ethylenediamine, di-2-hydroxyethylpropylenediamine, 2-hydroxypropylethylenediamine, or di-2-hydroxypropylethylenediamine, poly(propylene glycol) diamine, poly(propylene glycol) triamine, poly(propylene glycol) tetraamine, 1,2 -diaminopropane,
- 1,4-diaminobutane 1,5-diaminopentane, 1,6-diaminohexane, 1,7-diaminoheptane, 1,8-diaminooctane, 1,9-diaminononane, 1,10-diaminodecane, etc.
- benzyl Amine diethylenetriamine, dipropylenetriamine, triethylenetetramine, tripropylenetetramine, tetraethylenepentamine, tetrapropylenepentamine, pentaethylenehexamine, nonaethylenedecamine, trimethylhexamethylenediamine, etc., tetra(aminomethyl)methane, tetrakis ( 2-aminoethylaminomethyl)methane, 1,3-bis(2′-aminoethylamino)propane, triethylene-bis(trimethylene)hexamine, bis(3-aminoethy
- primary or secondary alkanolamines such as monoethanolamine, monoisopropanolamine, monobutanolamine, N-methylethanolamine, N-ethylethanolamine, N-methylpropanolamine, diethanolamine, diisopropanolamine (D2),
- D3 primary or secondary amines
- D3 such as ethylamine, octylamine, laurylamine, myristylamine, stearylamine, oleylamine, diethylamine, dibutylamine and distearylamine;
- the blending amount of the polyamine (D) is such that the amine value of the polyol composition (Y) is 20 to 70 mgKOH/g, more preferably 25. It is preferable to blend to 50 mg KOH/g.
- the amine value in this specification means the number of milligrams of KOH equivalent to the amount of HCl required to neutralize 1 g of the sample, and is not particularly limited, and can be calculated using a known method. can.
- the chemical structure of the amine compound (C) and, optionally, the average molecular weight, etc. are known, it can be calculated from (number of amino groups per molecule/average molecular weight) x 56.1 x 1000. can.
- the chemical structure, average molecular weight, etc. of the amine compound are unknown, it can be measured according to a known amine value measuring method such as JISK7237-1995.
- the adhesive of the present invention can accelerate the curing reaction by using a catalyst as necessary.
- the catalyst is not particularly limited as long as it promotes the urethanization reaction between the polyisocyanate composition (X) and the polyol composition (Y), and may be a metal catalyst (E1), an aliphatic cyclic amide compound (E2), or the like. are exemplified.
- Examples of the metal-based catalyst (E1) include metal complex-based, inorganic metal-based, and organic metal-based catalysts.
- the metal complex catalyst a group consisting of Fe (iron), Mn (manganese), Cu (copper), Zr (zirconium), Th (thorium), Ti (titanium), Al (aluminum), Co (cobalt)
- Examples include acetylacetonate salts of metals selected from the above, such as iron acetylacetonate, manganese acetylacetonate, copper acetylacetonate, zirconia acetylacetonate and the like. From the point of view of toxicity and catalytic activity, iron acetylacetonate (Fe(acac) 3 ) or manganese acetylacetonate (Mn(acac) 2 ) are preferred.
- inorganic metal-based catalysts examples include those selected from Sn, Fe, Mn, Cu, Zr, Th, Ti, Al, Co, and the like.
- Organometallic catalysts include organozinc compounds such as zinc octylate, zinc neodecanoate, and zinc naphthenate; , dioctyltin dilaurate, dibutyltin oxide, dibutyltin dichloride and other organic tin compounds, nickel octylate, nickel naphthenate and other organic nickel compounds, cobalt octylate, cobalt naphthenate and other organic cobalt compounds, bismuth octylate, neodecanoic acid At least one of organic bismuth compounds such as bismuth and bismuth naphthenate, tetraisopropyloxytitanate, dibutyltitanium dichloride, tetrabutyltitanate, butoxytitanium trichloride, aliphatic diketones, aromatic diketones, and alcohols having 2 to 10 carbon atoms.
- Examples of the aliphatic cyclic amide compound (E2) include ⁇ -valerolactam, ⁇ -caprolactam, ⁇ -enanthollactam, ⁇ -capryllactam, ⁇ -propiolactam and the like. Among these, ⁇ -caprolactam is more effective in accelerating hardening.
- These catalysts (E) can be used alone or in combination of two or more.
- the metal-based catalyst (E1) an adhesive having excellent sealing strength can be obtained.
- the aliphatic cyclic amide compound (E2) it is possible to obtain an adhesive that has excellent initial cohesive strength, adheres well to metal substrates, and does not easily cause poor appearance due to air bubbles. It is also preferable to use the metal-based catalyst (E1) and the aliphatic cyclic amide compound (E2) in combination.
- the amount of the catalyst (E1) to be blended is preferably 0.001 to 3 parts by mass with respect to 100 parts by mass of the total solid content of the polyisocyanate composition (X) and the polyol composition (Y), and 0.01 to 3 parts by mass. It is more preferable to use 2 parts by mass.
- the amount of the catalyst (E2) compounded is preferably 0.001 to 3 parts by mass with respect to 100 parts by mass of the total solid content of the polyisocyanate composition (X) and the polyol composition (Y), and 0.01 to 3 parts by mass. It is more preferable to use 2 parts by mass.
- the adhesive of the present invention may contain a pigment if necessary.
- the pigments used are not particularly limited, and extender pigments, white pigments, black pigments, gray pigments, red pigments, brown pigments, green pigments, and blue pigments described in the 1970 edition of the Handbook of Paint Materials (edited by the Japan Paint Manufacturers Association).
- Organic and inorganic pigments such as pigments, metal powder pigments, luminescent pigments, and pearlescent pigments, and plastic pigments can be used.
- Extender pigments include, for example, precipitated barium sulfate, rice flour, precipitated calcium carbonate, calcium bicarbonate, Kansui stone, alumina white, silica, hydrous fine silica (white carbon), ultrafine anhydrous silica (Aerosil), silica sand (silica sand), talc, precipitated magnesium carbonate, bentonite, clay, kaolin, loess, and the like.
- organic pigments include various insoluble azo pigments such as Benzidine Yellow, Hansa Yellow and Laked 4R; soluble azo pigments such as Laked C, Carmine 6B and Bordeaux 10; various (copper) pigments such as phthalocyanine blue and phthalocyanine green.
- insoluble azo pigments such as Benzidine Yellow, Hansa Yellow and Laked 4R
- soluble azo pigments such as Laked C, Carmine 6B and Bordeaux 10
- various (copper) pigments such as phthalocyanine blue and phthalocyanine green.
- Phthalocyanine pigments various chlorine dyeing lakes such as rhodamine lake and methyl violet lake; various mordant pigments such as quinoline lake and fast sky blue; various pigments such as anthraquinone pigments, thioindigo pigments and perinone pigments vat dye-based pigments; various quinacridone-based pigments such as Cincasia Red B; various dioxazine-based pigments such as dioxazine violet; various condensed azo pigments such as chromophtal;
- inorganic pigments include various chromates such as yellow lead, zinc chromate, molybdate orange; various ferrocyanic compounds such as Prussian blue; Various metal oxides such as zirconium oxide; various sulfides and selenides such as cadmium yellow, cadmium red, and mercury sulfide; various sulfates such as barium sulfate and lead sulfate; various types of silicon such as calcium silicate and ultramarine blue.
- chromates such as yellow lead, zinc chromate, molybdate orange
- ferrocyanic compounds such as Prussian blue
- metal oxides such as zirconium oxide
- various sulfides and selenides such as cadmium yellow, cadmium red, and mercury sulfide
- various sulfates such as barium sulfate and lead sulfate
- silicon such as calcium silicate and ultramarine blue.
- various acid salts such as calcium carbonate and magnesium carbonate; various phosphates such as cobalt violet and manganese purple; various metal powder pigments such as aluminum powder, gold powder, silver powder, copper powder, bronze powder and brass powder; These metal flake pigments and mica flake pigments; metallic pigments and pearl pigments such as mica-like iron oxide pigments and mica-like iron oxide pigments coated with metal oxides; graphite, carbon black and the like.
- plastic pigments examples include "Grandol PP-1000" and “PP-2000S” manufactured by DIC Corporation.
- the pigment to be used may be appropriately selected according to the purpose.
- inorganic oxides such as titanium oxide and zinc oxide are preferably used as white pigments because they are excellent in durability, weather resistance, and design.
- Carbon black is preferably used as the pigment.
- the amount of the pigment compounded is, for example, 1 to 400 parts by mass with respect to 100 parts by mass of the total solid content of the polyisocyanate composition (X) and the polyol composition (Y). 10 to 300 parts by mass is more preferable.
- the adhesive of the present invention may contain an adhesion promoter.
- adhesion promoters include coupling agents such as silane coupling agents, titanate coupling agents and aluminum coupling agents, and epoxy resins.
- Silane coupling agents include ⁇ -aminopropyltriethoxysilane, ⁇ -aminopropyltrimethoxysilane, N- ⁇ (aminoethyl)- ⁇ -aminopropyltrimethoxysilane, N- ⁇ (aminoethyl)- ⁇ -amino Aminosilanes such as propyltrimethyldimethoxysilane and N-phenyl- ⁇ -aminopropyltrimethoxysilane; ⁇ -(3,4-epoxycyclohexyl)ethyltrimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxy epoxysilanes such as propyltriethoxysilane; vinylsilanes such as vinyltris( ⁇ -methoxyethoxy)silane, vinyltriethoxysilane, vinyltrimethoxysilane, ⁇ -methacryloxypropyl
- Titanate-based coupling agents include, for example, tetraisopropoxytitanium, tetra-n-butoxytitanium, butyl titanate dimer, tetrastearyl titanate, titanium acetylacetonate, titanium lactate, tetraoctylene glycol titanate, titanium lactate, tetrastearoxy Titanium etc. are mentioned.
- aluminum-based coupling agents examples include acetoalkoxyaluminum diisopropylate.
- epoxy resin generally commercially available epibis type, novolac type, ⁇ -methyl epichloro type, cyclic oxirane type, glycidyl ether type, glycidyl ester type, polyglycol ether type, glycol ether type, epoxidized fatty acid ester type, poly Various epoxy resins such as carboxylic acid ester type, aminoglycidyl type, resorcinol type, triglycidyl tris(2-hydroxyethyl) isocyanurate, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, acryl glycidyl compounds such as ether, 2-ethylhexyl glycidyl ether, phenyl glycidyl ether, phenol glycidyl ether, pt-butylphenyl glycidyl ether, diglycidyl
- the adhesive of the present invention includes a leveling agent, inorganic fine particles such as colloidal silica and alumina sol, organic fine particles of polymethyl methacrylate, antifoaming agent, anti-sagging agent, wetting and dispersing agent, and viscosity modifier.
- UV absorber metal deactivator, peroxide decomposer, flame retardant, reinforcing agent, plasticizer, lubricant, rust inhibitor, fluorescent whitening agent, inorganic heat ray absorber, flame retardant, electrification Inhibitors, dehydrating agents, known and commonly used thermoplastic elastomers, tackifiers, phosphoric compounds, melamine resins, reactive elastomers and the like may also be included.
- dehydrating agents known and commonly used thermoplastic elastomers, tackifiers, phosphoric compounds, melamine resins, reactive elastomers and the like may also be included.
- the blending amount of these additives is appropriately adjusted within a range that does not impair the desired properties of the adhesive of the present invention.
- plasticizers examples include phthalic acid-based plasticizers, fatty acid-based plasticizers, aromatic polycarboxylic acid-based plasticizers, phosphoric acid-based plasticizers, polyol-based plasticizers, epoxy-based plasticizers, polyester-based plasticizers, and carbonate-based plasticizers. plasticizers, and the like.
- phthalic plasticizers include dimethyl phthalate, diethyl phthalate, dibutyl phthalate, diisobutyl phthalate, dihexyl phthalate, diheptyl phthalate, di-(2-ethylhexyl) phthalate, di-n-octyl phthalate, dinonyl phthalate, diisononyl phthalate, didecyl phthalate, diisodecyl phthalate, ditridecyl phthalate, diundecyl phthalate, dilauryl phthalate, distearyl phthalate, diphenyl phthalate, dibenzyl phthalate, butylbenzyl phthalate, dicyclohexyl phthalate, octyldecyl phthalate, dimethyl isophthalate, Phthalic ester plasticizers such as di-(2-ethylhexyl) isophthalate and diisooc
- fatty acid-based plasticizers include adipic acids such as di-n-butyl adipate, di-(2-ethylhexyl) adipate, diisodecyl adipate, diisononyl adipate, di(C6-C10 alkyl) adipate, and dibutyl diglycol adipate.
- adipic acids such as di-n-butyl adipate, di-(2-ethylhexyl) adipate, diisodecyl adipate, diisononyl adipate, di(C6-C10 alkyl) adipate, and dibutyl diglycol adipate.
- azelaic acid plasticizers such as di-n-hexyl azelate, di-(2-ethylhexyl) azelate, diisooctyl azelate, di-n-butyl sebacate, di-(2- ethylhexyl) sebacate, diisononyl sebacate and other sebacic acid plasticizers, e.g.
- di-n-butyl fumarate, di-(2-ethylhexyl) fumarate and other fumaric acid plasticizers such as monomethyl itaconate, monobutyl itaconate, dimethyl itaconate, diethyl itaconate, dibutyl itaconate, Itaconic acid plasticizers such as di-(2-ethylhexyl) itaconate, stearic acid plasticizers such as n-butyl stearate, glycerin monostearate, diethylene glycol distearate, butyl oleate, glyceryl monooleate, Oleic acid plasticizers such as diethylene glycol monooleate, citric acid such as triethyl citrate, tri-n-butyl citrate, acetyltriethyl citrate, acetyltributyl citrate, acetyl tri-(2-ethylhexyl) citrate ric acid
- aromatic polycarboxylic acid-based plasticizers include tri-n-hexyl trimellitate, tri-(2-ethylhexyl) trimellitate, tri-n-octyl trimellitate, triisooctyl trimellitate, and triisononyl. trimellitate, tridecyl trimellitate, triisodecyl trimellitate and other trimellitic acid plasticizers, e.g., tetra-(2-ethylhexyl) pyromellitate, tetra-n-octyl pyromellitate and other pyromellitic acid plasticizers plasticizers, and the like.
- Phosphate plasticizers include, for example, triethyl phosphate, tributyl phosphate, tri-(2-ethylhexyl) phosphate, tributoxyethyl phosphate, triphenyl phosphate, octyldiphenyl phosphate, cresyldiphenyl phosphate, cresylphenyl phosphate, trichlé Zyl phosphate, trixylenyl phosphate, tris(chloroethyl) phosphate, tris(chloropropyl) phosphate, tris(dichloropropyl) phosphate, tris(isopropylphenyl) phosphate and the like.
- polyol plasticizers examples include diethylene glycol dibenzoate, dipropylene glycol dibenzoate, triethylene glycol dibenzoate, triethylene glycol di-(2-ethylbutyrate), triethylene glycol di-(2-ethylhexoate ), glycol-based plasticizers such as dibutylmethylene bisthioglycolate, and glycerin-based plasticizers such as glycerol monoacetate, glycerol triacetate, and glycerol tributyrate.
- glycol-based plasticizers such as dibutylmethylene bisthioglycolate
- glycerin-based plasticizers such as glycerol monoacetate, glycerol triacetate, and glycerol tributyrate.
- epoxy plasticizers include epoxidized soybean oil, epoxybutyl stearate, di-2-ethylhexyl epoxyhexahydrophthalate, diisodecyl epoxyhexahydrophthalate, epoxy triglyceride, epoxidized octyl oleate, and epoxidized decyl oleate. etc.
- polyester-based plasticizers examples include adipic acid-based polyesters, sebacic acid-based polyesters, and phthalic acid-based polyesters.
- Propylene carbonate and ethylene carbonate are examples of carbonate-based plasticizers.
- plasticizers include partially hydrogenated terphenyl, adhesive plasticizers, diallyl phthalate, polymerizable plasticizers such as acrylic monomers and oligomers, and the like. These plasticizers can be used alone or in combination of two or more.
- the laminate of the invention can be obtained by a known method. For example, after premixing the polyisocyanate composition (X) and the polyol composition (Y), it is applied to a first substrate, then a second substrate is laminated on the coated surface, and an adhesive layer is formed.
- one substrate is coated with a mixture of the polyisocyanate composition (X) and a compound having an active hydrogen group, and the other substrate is coated with the polyol composition (Y). After processing, it is also preferable to laminate these substrates by contacting and press-bonding the respective coated surfaces to cure the adhesive layer.
- the compound having an active hydrogen group to be mixed with the polyisocyanate composition (X) those exemplified as the polyol (B) and the compound (C) can be used.
- the adhesive of the present invention in a method having a separate coating step, since it is easier to secure time for the polyol composition (Y) to wet and spread on the substrate.
- the polyisocyanate composition (X) and the polyol composition (Y) are coated on separate substrates and before they are brought into contact with each other, the polyisocyanate composition (X) and the polyol composition (Y) are It can sufficiently wet and spread on the base material.
- the polyol composition (Y) is applied onto the vapor deposited aluminum layer of the substrate having the vapor deposited aluminum layer, and the polyisocyanate composition (X) is applied to the other substrate. coating, and contacting and press-bonding the polyisocyanate composition (X) and the polyol composition (Y).
- Solvent-free adhesives are often inferior in adhesion to the vapor-deposited aluminum layer. can be
- the polyisocyanate composition (X) is applied onto the printed layer of a base material having a printed layer, and the polyol composition (Y) is applied to the other base material. coating, and contacting and press-bonding the polyisocyanate composition (X) and the polyol composition (Y).
- the printed layer and another substrate are bonded together using a solvent-free adhesive, the printed layer may be dissolved by the adhesive, resulting in poor appearance.
- the coating amount of the adhesive is, for example, 0.5 to 5.0 g/ m2 .
- the coating amounts of the polyisocyanate composition (X) and the polyol composition (Y) are each 0.3 to 3.0 g/ m 2 is preferable, and it is more preferable to use about 0.3 to 2.0 g/m 2 .
- the crimping method is preferably a method of laminating by pressure between two rolls (laminating rolls) while passing between them.
- the temperature of the laminating rolls is preferably room temperature to about 80°C, and the pressure is preferably about 0.05 to 0.5 MPa.
- the two-component curing adhesive of the present invention when used, after lamination, at room temperature (20 to 25° C.) or under heating, more specifically 15 to 35° C., 12 The adhesive cures in ⁇ 72 hours and develops practical physical properties.
- the laminate of the present invention is obtained by laminating a plurality of substrates by the method described above. Further, another base material can be attached to the laminate of the present invention.
- the adhesive used at this time may be the one described above, or may be a general-purpose two-liquid curing adhesive.
- a dry lamination method or a non-solvent lamination method may be used, or a separate coating method may be used.
- Base material 1/adhesive layer 1/sealant film (2) Base material 1/adhesive layer 1/metal vapor deposition unstretched film (3) Base material 1/adhesive layer 1/metal vapor deposition stretched film (4) Transparent vapor deposition stretching Film/adhesive layer 1/sealant film (5) Substrate 1/adhesive layer 1/substrate 2/adhesive layer 2/sealant film (6) Substrate 1/adhesive layer 1/stretched metal deposition film/adhesive layer 2/sealant Film (7) Substrate 1/adhesive layer 1/transparent evaporated stretched film/adhesive layer 2/sealant film (8) Substrate 1/adhesive layer 1/metal layer/adhesive layer 2/sealant film (9) Substrate 1/ Adhesive layer 1/substrate
- Examples of the base material 1 used in configuration (1) include OPP film, PET film, nylon film, paper, and the like. Further, as the base material 1, a material coated for the purpose of improving gas barrier properties and ink receptivity when providing a printing layer, which will be described later, may be used. Commercial products of the coated base film 1 include K-OPP film and K-PET film.
- the adhesive layer 1 is a cured coating film of the adhesive of the present invention. Examples of sealant films include CPP films and LLDPE films. On the surface of the substrate 1 on the side of the adhesive layer 1 (the surface of the coating layer on the side of the adhesive layer 1 when a coated substrate film 1 is used) or the surface opposite to the adhesive layer 1, A printing layer may be provided.
- the printing layer is formed by general printing methods conventionally used for printing on polymer films and paper using various printing inks such as gravure ink, flexographic ink, offset ink, stencil ink, and inkjet ink.
- the base material 1 used in configurations (2) and (3) examples include OPP film, PET film, paper, and the like.
- the adhesive layer 1 is a cured coating film of the adhesive of the present invention.
- a VM-CPP film obtained by vapor-depositing a metal such as aluminum on a CPP film may be used as the unstretched metal vapor-deposited film, and a VM-OPP film obtained by vapor-depositing a metal such as aluminum on an OPP film may be used as the stretched metal-deposited film. can be done.
- a printed layer may be provided on either side of the substrate 1 in the same manner as in configuration (1).
- Examples of transparent vapor-deposited stretched films used in configuration (4) include films obtained by vapor-depositing silica or alumina on OPP films, PET films, nylon films, or the like.
- a film obtained by coating the deposition layer may be used.
- the adhesive layer 1 is a cured coating film of the adhesive of the present invention.
- Examples of the sealant film include those similar to those of the configuration (1).
- a printed layer may be provided on the adhesive layer 1 side of the transparent vapor deposited stretched film (when using a film having a coated inorganic vapor deposited layer, the surface of the coating layer on the adhesive layer 1 side). The method of forming the printed layer is the same as that of configuration (1).
- Examples of the base material 1 used in configuration (5) include PET film, paper, and the like.
- Examples of the base material 2 include a nylon film and the like.
- At least one of adhesive layer 1 and adhesive layer 2 is a cured coating film of the adhesive of the present invention.
- Examples of the sealant film include those similar to those of the configuration (1).
- a printed layer may be provided on either side of the substrate 1 in the same manner as in configuration (1).
- the same ones as those of configurations (2) and (3) can be mentioned.
- the metal-deposited oriented film include VM-OPP film and VM-PET film obtained by subjecting an OPP film or PET film to metal deposition such as aluminum.
- At least one of adhesive layer 1 and adhesive layer 2 is a cured coating film of the adhesive of the present invention.
- the sealant film include those similar to those of the configuration (1).
- a printed layer may be provided on either side of the substrate 1 in the same manner as in configuration (1).
- Examples of the base material 1 of configuration (7) include PET film, paper, and the like. Examples of the transparent vapor-deposited stretched film include those similar to those of the configuration (4). At least one of the adhesive layers 1 and 2 is a cured coating film of the adhesive of the present invention. Examples of the sealant film include those similar to those of the configuration (1). A printed layer may be provided on either side of the substrate 1 in the same manner as in configuration (1).
- Examples of the base material 1 of configuration (8) include PET film, paper, and the like. Aluminum foil etc. are mentioned as a metal layer. At least one of the adhesive layers 1 and 2 is a cured coating film of the adhesive of the present invention. Examples of the sealant film include those similar to those of the configuration (1). A printed layer may be provided on either side of the substrate 1 in the same manner as in configuration (1).
- Examples of the substrate 1 of configurations (9) and (10) include PET film, paper, and the like.
- Examples of the base material 2 include a nylon film and the like. Aluminum foil etc. are mentioned as a metal layer.
- At least one of the adhesive layers 1, 2 and 3 is a cured coating film of the adhesive of the present invention.
- Examples of the sealant film include those similar to those of the configuration (1).
- a printed layer may be provided on either side of the substrate 1 in the same manner as in configuration (1).
- the packaging material of the present invention is obtained by molding the laminate of the present invention into a bag shape.
- the laminate of the present invention is folded or overlapped so that the inner layer surface (sealant film surface) faces each other, and the peripheral edge is sealed, for example, by a side seal type, a two-sided seal type, There are three-side seal type, four-side seal type, envelope seal type, palm-joint seal type, pleated seal type, flat-bottom seal type, square-bottom seal type, gusset type, and other heat-sealing methods. be done.
- the packaging material of the present invention can take various forms depending on the contents, environment of use, and form of use.
- a self-supporting packaging material (standing pouch) or the like is also possible.
- a heat sealing method known methods such as bar sealing, rotary roll sealing, belt sealing, impulse sealing, high frequency sealing and ultrasonic sealing can be used.
- An easy-opening treatment or resealing means may be provided.
- the packaging material of the present invention can be used industrially as a packaging material mainly filled with foods, detergents, and medicines. Specific uses include detergents and chemicals such as liquid laundry detergents, liquid kitchen detergents, liquid bath detergents, liquid bath soaps, liquid shampoos, liquid conditioners, and pharmaceutical tablets. It can also be used as a secondary packaging material for packaging the container described above.
- Polyisocyanate composition (X-1) 40.2 parts of 4,4-diphenylmethane diisocyanate (hereinafter abbreviated as "MDI”) and hexamethylene diisocyanate nurate (hereinafter, “HDI nurate”) are added to a flask equipped with a stirrer, thermometer, and nitrogen gas inlet tube. ”): 10.0 parts were charged into a reaction vessel, stirred under nitrogen gas, and heated to 60°C.
- MDI 4,4-diphenylmethane diisocyanate
- HDI nurate hexamethylene diisocyanate nurate
- Polyol compositions (Y-1) to (Y-13) and (Y'-1) to (Y'-3) were prepared according to the formulations shown in Tables 1 to 3.
- the compounds in the table are as follows.
- Polyisocyanate composition (X) was used for corona-treated PET film (thickness 12 ⁇ m), and polyol composition (Y) was used for VMCPP film (thickness 25 ⁇ m) at processing speeds of 100, 150, 200, and 250 m/min. glued to each other.
- the coating amounts (g/m 2 ) of the polyisocyanate composition (X) and the polyol composition (Y) are shown in Tables 4 and 5. After aging at 25° C. for 24 hours, the presence or absence of air bubbles remaining in the laminate was checked, and the processing speed range in which no air bubbles remained was examined. The results were summarized in Tables 4 and 5 after evaluation by the following 5-grade evaluation.
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Abstract
Description
本発明の接着剤はポリイソシアネート組成物(X)と、ポリオール組成物(Y)と、を含む2液硬化型である。以下、本発明の接着剤について詳細に説明する。
(ポリイソシアネート化合物(A))
ポリイソシアネート組成物(X)は、複数のイソシアネート基を有するポリイソシアネート化合物(A)を含む。ポリイソシアネート化合物(A)としては特に限定されず、芳香族ジイソシアネート、芳香脂肪族ジイソシアネート、脂肪族ジイソシアネート、脂環族ジイソシアネート、及びこれらジイソシアネートのビュレット体、ヌレート体、アダクト体、アロファネート体、カルボジイミド変性体、ウレトジオン変性体、これらポリイソシアネートとポリオールを反応させたウレタンプレポリマー等が挙げられ、これらを単独でまたは複数組み合わせて使用することができる。
ダイマージオール;
ビスヒドロキシエトキシベンゼン;
ジエチレングリコール、トリエチレングリコール、その他のポリエチレングリコール、ポリプロピレングリコール、ポリブチレングリコール等のポリアルキレングリコール;
ポリアルキレングリコールを更に芳香族又は脂肪族ポリイソシアネートで高分子量化したウレタン結合含有ポリエーテルポリオール;
プロピオラクトン、ブチロラクトン、ε-カプロラクトン、σ-バレロラクトン、β-メチル-σ-バレロラクトン等の環状エステル化合物の開環重合反応によって得られるポリエステルと、グリコール、グリセリン、トリメチロールプロパン、ペンタエリスリトール等の多価アルコールとの反応物であるポリエステルポリオール等が挙げられる。
ポリイソシアネート(a1-1)は4,4’-ジフェニルメタンジイソシアネートを含むが、他のポリイソシアネート化合物を含んでいてもよい。4,4’-ジフェニルメタンジイソシアネートと併用可能なポリイソシアネート化合物としては特に制限されず、ポリイソシアネート化合物(A)として例示したものを1種または2種以上組み合わせて用いることができる。ポリイソシアネート(a1-1)に占める4,4’-ジフェニルメタンジイソシアネートの配合量は、40~99質量%であることが好ましく、75~90質量%であることが好ましい。
カラム ;東ソー株式会社製 TSKgel 4000HXL、TSKgel 3000HXL、TSKgel 2000HXL、TSKgel 1000HXL
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)
ポリイソシアネート組成物(X)は、ウレタンプレポリマー(A1)以外のイソシアネート化合物(A2)を含んでいてもよい。イソシアネート化合物(A2)としては、ポリイソシアネート化合物(A)として例示したものを適宜用いることができる。カルボジイミド変性ジイソシアネートやポリメチレンポリフェニルポリイソシアネート(ポリメリックMDI、あるいはクルードMDIとも称される)が好ましい。
(ポリオール(B))
本発明に用いられるポリオール(B)としては特に限定されず、エチレングリコール、プロピレングリコール、1,3-プロパンジオール、1,4-ブタンジオール、1,5-ペンタンジオール、3-メチル-1,5-ペンタンジオール、1,6-ヘキサンジオール、ネオペンチルグリコール、メチルペンタンジオール、ジメチルブタンジオール、ブチルエチルプロパンジオール、ジエチレングリコール、トリエチレングリコール、テトラエチレングリコール、ジプロピレングリコール、トリプロピレングリコール、ビスヒドロキシエトキシベンゼン、1,4-シクロヘキサンジオール、1,4-シクロヘキサンジメタノール、トリエチレングリコール等のグリコール;
グリセリン、トリメチロールプロパン、ペンタエリスリトール、ポリプロピレングリコールのトリオール体等の3官能又は4官能の脂肪族アルコール;
ビスフェノールA、ビスフェノールF、水素添加ビスフェノールA、水素添加ビスフェノールF等のビスフェノール;
ダイマージオール;
前記グリコール、ダイマージオール、又は前記ビスフェノール等の2官能型ポリオールと、多価カルボン酸とを反応させて得られるポリエステルポリオール(2);
前記3官能又は4官能の脂肪族アルコールと、多価カルボン酸とを反応させて得られるポリエステルポリオール(3);
前記グリコール、ダイマージオール、又は前記ビスフェノール等の2官能型ポリオールと、前記3官能又は4官能の脂肪族アルコールと、多価カルボン酸とを反応させて得られるポリエステルポリオール(4);
ジメチロールプロピオン酸、ひまし油脂肪酸等のヒドロキシル酸の重合体である、ポリエステルポリオール(5);
前記ポリエーテルポリオールと、前記グリコール、ダイマージオール、ビスフェノール等の2官能型ポリオール、3官能又は4官能の脂肪族アルコールからなる群から選ばれる少なくとも一種と、多価カルボン酸とを反応させて得られるポリエーテルポリエステルポリオール;
40℃程度の比較的低温での加温でも塗工性に優れた接着剤となることからポリオール(B)はポリエーテルポリオール(B1)または植物油ポリオール(B2)の少なくとも一種を含むことが好ましい。塗工適性の観点から、ポリオール(B)におけるポリエーテルポリオール(B1)または植物油ポリオール(B2)の配合量は、20質量%以上であることが好ましく、30質量%であることがより好ましい。100質量%であってもよいが、より好ましくは80質量%以下である。
本発明において、ポリオール(B)はポリエステルポリオール(B3)を含むことが好ましい。これにより、ナイロンフィルムなどの硬質フィルムとの接着性を向上させることができる。
本発明に用いられる化合物(C)は、2,2-ジメチロール酢酸、2,2-ジメチロールプロピオン酸、2,2-ジメチロールブタン酸、2,2-ジメチロールペンタン酸からなる群から選ばれる少なくとも一種であり、2,2-ジメチロールプロピオン酸、2,2-ジメチロールブタン酸の少なくとも一種を含むことが好ましく、2,2-ジメチロールプロピオン酸を含むことがより好ましい。ポリオール組成物(Y)が化合物(C)を含むことにより、金属基材への密着性、ポットライフに優れた接着剤とすることができる。
ポリオール組成物(Y)は、複数のアミノ基を有するポリアミン(D)を含むことが好ましい。本明細書においてアミノ基とは、NH2基またはNHR基(Rは官能基を有していてもよいアルキル基またはアリール基)をいう。ポリオール組成物がポリアミン(D)を含むことにより、またバリア性の基材を貼り合わせる場合にも外観が良好な積層体を得ることができる。
本発明の接着剤は必要に応じて触媒を使用することにより硬化反応を促進することができる。触媒としては、ポリイソシアネート組成物(X)とポリオール組成物(Y)のウレタン化反応を促進するものであれば特に制限されず、金属系触媒(E1)、脂肪族環状アミド化合物(E2)等が例示される。
本発明の接着剤は、必要に応じて顔料を含んでいてもよい。用いられる顔料としては特に制限はなく、塗料原料便覧1970年度版(日本塗料工業会編)に記載されている体質顔料、白顔料、黒顔料、灰色顔料、赤色顔料、茶色顔料、緑色顔料、青顔料、金属粉顔料、発光顔料、真珠色顔料等の有機顔料や無機顔料、さらにはプラスチック顔料などが挙げられる。
本発明の接着剤は、接着促進剤を含んでいてもよい。接着促進剤としては、シランカップリング剤、チタネート系カップリング剤、アルミニウム系カップリング剤等のカップリング剤、エポキシ樹脂等が挙げられる。
本発明の接着剤は、上述した成分以外に、レベリング剤、コロイド状シリカやアルミナゾルなどの無機微粒子、ポリメチルメタクリレート系の有機微粒子、消泡剤、タレ性防止剤、湿潤分散剤、粘性調整剤、紫外線吸収剤、金属不活性化剤、過酸化物分解剤、難燃剤、補強剤、可塑剤、潤滑剤、防錆剤、蛍光性増白剤、無機系熱線吸収剤、防炎剤、帯電防止剤、脱水剤、公知慣用の熱可塑性エラストマー、粘着付与剤、燐酸化合物、メラミン樹脂、反応性エラストマー等を含んでいてもよい。これらの添加剤の配合量は、本発明の接着剤の希望を損なわない範囲で適宜調整される。
本発明の積層体は、公知の方法で得ることができる。例えばポリイソシアネート組成物(X)とポリオール組成物(Y)とを事前に混ぜ合わせた後、第一の基材に塗布し、次いで塗布面に第二の基材を積層し、接着剤層を硬化させて得る2液混合工程を有する方法や、ポリイソシアネート組成物(X)と、組成物ポリオール(Y)とを第一の基材及び第二の基材に別々に塗布後、それぞれの塗布面を接触させ圧着させることにより第一の基材と第二の基材とを積層させ、接着剤層を硬化させて得る2液分別塗工工程を有する方法により得られる。
本発明の積層体は、複数の基材を上述の方法にて貼り合わせて得られる。また、本発明の積層体に、さらに他の基材を貼り合わせることもできる。この際用いる接着剤は上述のものであってもよいし、汎用の2液硬化型接着剤であってもよい。また、本発明の方法で得られた積層体にさらに他の基材を貼り合わせる場合、ドライラミネート法またはノンソルベントラミネート法を用いてもよいし、分別塗工方法を用いてもよい。
(1)基材1/接着層1/シーラントフィルム
(2)基材1/接着層1/金属蒸着未延伸フィルム
(3)基材1/接着層1/金属蒸着延伸フィルム
(4)透明蒸着延伸フィルム/接着層1/シーラントフィルム
(5)基材1/接着層1/基材2/接着層2/シーラントフィルム
(6)基材1/接着層1/金属蒸着延伸フィルム/接着層2/シーラントフィルム
(7)基材1/接着層1/透明蒸着延伸フィルム/接着層2/シーラントフィルム
(8)基材1/接着層1/金属層/接着層2/シーラントフィルム
(9)基材1/接着層1/基材2/接着層2/金属層/接着層3/シーラントフィルム
(10)基材1/接着層1/金属層/接着層2/基材2/接着層3/シーラントフィルム
等が挙げられるがこれに限定されない。
本発明の包装材は、本発明の積層体を袋状に成型してなる。製袋方法としては、本発明の積層体を折り曲げるか、あるいは重ねあわせてその内層の面(シーラントフィルムの面)を対向させ、その周辺端部を、例えば、側面シール型、二方シール型、三方シール型、四方シール型、封筒貼りシール型、合掌貼りシール型、ひだ付シール型、平底シール型、角底シール型、ガゼット型、その他のヒートシール型等の形態によりヒートシールする方法が挙げられる。本発明の包装材は内容物や使用環境、使用形態に応じて種々の形態をとり得る。自立性包装材(スタンディングパウチ)等も可能である。ヒートシールの方法としては、バーシール、回転ロールシール、ベルトシール、インパルスシール、高周波シール、超音波シール等の公知の方法で行うことができる。易開封処理や再封性手段が設けられていてもよい。
(ポリイソシアネート組成物(X-1))
撹拌機、温度計、窒素ガス導入管を備えたフラスコに、4,4-ジフェニルメタンジイソシアネート(以下、「MDI」と略記する):40.2部と、ヘキサメチレンジイソシアネートヌレート体(以下、「HDIヌレート」と略記する):10.0部とを反応容器内に仕込み、窒素ガス下で攪拌し、60℃まで加熱した。このフラスコに、さらに数平均分子量1000の2官能のポリプロピレングリコール(以下、「PPG」と略記する。):37.9部と、2,2,4-トリメチル-1,3-ペンタンジオール:2.0部とを混合して数回に分けて滴下し、80℃で5~6時間攪拌してウレタン化反応させることにより、ポリイソシアネートを得た。得られたポリイソシアネートを、カルボジイミド変性イソシアネート:10.0部と混合し、ポリイソシアネート組成物(X-1)を得た。
表1~3に示す配合で、ポリオール組成物(Y-1)~(Y-13)、(Y’-1)~(Y’-3)を調整した。表中の化合物は以下の通りである。
ポリオール(B1-1-1):アクトコールD-1000(三井化学社製、数平均分子量1000、2官能のポリプロピレンポリオール)
ポリオール(B1-1-2):アクトコールT-1000(三井化学社製、数平均分子量1000、3官能のポリプロピレンポリオール)
ポリオール(B1-1-3):アクトコールD-400(三井化学社製、数平均分子量400、2官能のポリプロピレンポリオール)
ポリオール(B1):D-4000(三井化学社製、数平均分子量4000、2官能のポリプロピレンポリオール)
ポリオール(B1-2):サンニックスHD-402(三洋化成工業社製、数平均分子量600、4官能のポリプロピレンポリオール)
ポリオール(B2):ひまし油
ポリオール(B3):クラレポリオールF-510(トリメチロールプロパン、3-メチル-1,5-ペンタンジオール、アジピン酸からなる重量平均分子量500のポリエステルトリオール)
化合物(C-1):ジメチロールプロピオン酸
化合物(C-2):ジメチロールブタン酸
ポリアミン(D1):ジェファーミン T-403(Huntsman社製、ポリオキシプロピレントリアミン、Mw=400、アミン価=355mgKOH/g)
ポリアミン(D2):モノエタノールアミン
ポリアミン(D3):ジエチルアミン
触媒(E1-1):BiCAT8(Shepherd社製、ネオデカン酸ビスマスとネオデカン酸亜鉛の混合物)
触媒(E1-2):ジラウリル酸ジブチルすず
触媒(E2):ε-カプロラクタム
KBM-403:信越シリコーン製、3-グリシドキシプロピルトリメトキシシラン
KBE-903:信越シリコーン製、3-アミノプロピルトリエトキシシラン
レベリング剤:サーフィノール420(EVONIK社製、アセチレン系ジアルコールのポリエーテル化物)
(ラミネート強度 OPP/VMCPP)
OPPフィルム(東洋紡社製、P2161)に加温したポリイソシアネート組成物(X)を、VMCPPフィルム(東レフィルム加工社製、2703)に加温したポリオール組成物(Y)を塗布し、OPPフィルムとVMCPPフィルムとをニップロール(50℃)で圧着し、25℃で24時間エージングしてOPP/接着層/VMCPPの積層体1を得た。ポリイソシアネート組成物(X)、ポリオール組成物(Y)の塗布量(g/m2)は表4、5に示す通りである。
5:1.5N/15mm以上
4:1.0N/15mm以上1.5N/15mm未満
3:0.5N/15mm以上1.0N/15mm未満
2:0.2N/15mm以上0.5N/15mm未満
1:0.2N/15mm未満
OPPフィルム(東洋紡社製、P2161)に加温したポリイソシアネート組成物(X)を、CPPフィルム(東洋紡社製、P1128)に加温したポリオール組成物(Y)を塗布し、OPPフィルムとCPPフィルムとをニップロール(50℃)で圧着してOPP/接着層/CPPの積層体2を得た。ポリイソシアネート組成物(X)、ポリオール組成物(Y)の塗布量(g/m2)は表4、5に示す通りである。積層体1と同様にしてラミネート強度を測定、評価し、結果を表4、5にまとめた。
コロナ処理PETフィルム(厚さ12μm)にポリイソシアネート組成物(X)を、VMCPPフィルム(厚さ25μm)にポリオール組成物(Y)を使用し、100、150、200、250m/minの加工速度でそれぞれ貼り合わせた。ポリイソシアネート組成物(X)、ポリオール組成物(Y)の塗布量(g/m2)は表4、5に示す通りである。25℃、24時間エージングした後、積層体に残存している気泡の有無を確認し、気泡が残存していない加工速度域を調べた。以下の5段階評価で評価し、結果を表4、5にまとめた。
5:100~250m/minで気泡残存なし
4:100~200m/minで気泡残存なし
3:100~150m/minで気泡残存なし
2:100m/minで気泡残存なし
1:100m/minで気泡残存あり
Claims (11)
- ポリイソシアネート組成物(X)と、ポリオール組成物(Y)と、を含み、
前記ポリイソシアネート組成物(X)はポリイソシアネート化合物(A)を含み、
前記ポリオール組成物(Y)はポリオール(B)と、2,2-ジメチロール酢酸、2,2-ジメチロールプロピオン酸、2,2-ジメチロールブタン酸、2,2-ジメチロールペンタン酸からなる群から選ばれる少なくとも一種である化合物(C)とを含むことを特徴とする、2液硬化型接着剤。 - 前記ポリオール組成物(Y)は、ポリアミン(D)を含む請求項1に記載の2液硬化型接着剤。
- 前記ポリオール(B)が、ポリエーテルポリオール(B1)または植物油ポリオール(B2)の少なくとも一種を含む請求項1または2のいずれか一項に記載の2液硬化型接着剤。
- 前記ポリオール(B)が、は数平均分子量が130以上3000以下のポリエーテルジオール(B1-1)を含む請求項1~3のいずれか一項に記載の2液硬化型接着剤。
- 前記ポリオール(B)が、3官能以上のポリエーテルポリオール(B1-2)を含む請求項1~4のいずれか一項に記載の2液硬化型接着剤。
- 前記ポリオール(B)が、ポリエステルポリオール(B3)を含む請求項1~5のいずれか一項に記載の2液硬化型接着剤。
- 前記ポリエステルポリオール(B3)が、多価カルボン酸と多価アルコールとを含む組成物の反応生成物であって、前記多価カルボン酸に占める脂肪族多価カルボン酸の配合量が80質量%以上であり、前記多価アルコールに占める脂肪族多価アルコールの配合量が80質量%以上である請求項6に記載の2液硬化型接着剤。
- 前記ポリオール組成物(Y)が、ウレタン化触媒(E)を含む請求項1~7のいずれか一項に記載の2液硬化型接着剤。
- 第1の基材と、第2の基材と、前記第1の基材と前記第2の基材とを貼り合せる接着層とを含み、前記接着層が請求項1~8のいずれか一項に記載の接着剤の硬化塗膜であることを特徴とする積層体。
- 第一の基材にポリイソシアネート組成物(X)を塗布する工程と、
第二の基材にポリオール組成物(Y)を塗布する工程と、
前記第1の基材と前記第2の基材とを、前記ポリイソシアネート組成物(X)と前記ポリオール組成物(Y)とが接触するように貼り合わせる工程とを含む積層体の製造方法。 - 請求項9に記載の積層体からなる包装材。
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