WO2020180924A1 - Two-component solvent-based adhesive composition - Google Patents
Two-component solvent-based adhesive composition Download PDFInfo
- Publication number
- WO2020180924A1 WO2020180924A1 PCT/US2020/020878 US2020020878W WO2020180924A1 WO 2020180924 A1 WO2020180924 A1 WO 2020180924A1 US 2020020878 W US2020020878 W US 2020020878W WO 2020180924 A1 WO2020180924 A1 WO 2020180924A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- component
- polyol
- solvent
- mol
- adhesive composition
- Prior art date
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- 239000002904 solvent Substances 0.000 title claims abstract description 110
- 239000000203 mixture Substances 0.000 title claims abstract description 109
- 239000000853 adhesive Substances 0.000 title claims abstract description 92
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 92
- 229920005862 polyol Polymers 0.000 claims abstract description 129
- 150000003077 polyols Chemical class 0.000 claims abstract description 128
- 239000012948 isocyanate Substances 0.000 claims abstract description 76
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 57
- 239000004417 polycarbonate Substances 0.000 claims abstract description 35
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 24
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 20
- 229920006149 polyester-amide block copolymer Polymers 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 15
- 239000000758 substrate Substances 0.000 claims description 66
- -1 aromatic isocyanate Chemical class 0.000 claims description 32
- 238000012360 testing method Methods 0.000 claims description 22
- 239000012790 adhesive layer Substances 0.000 claims description 21
- 239000011888 foil Substances 0.000 claims description 17
- 229910052751 metal Inorganic materials 0.000 claims description 15
- 239000002184 metal Substances 0.000 claims description 15
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 14
- 229920001684 low density polyethylene Polymers 0.000 claims description 14
- 239000004702 low-density polyethylene Substances 0.000 claims description 14
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 11
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 11
- 125000001033 ether group Chemical group 0.000 claims description 10
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 9
- 239000001361 adipic acid Substances 0.000 claims description 7
- 235000011037 adipic acid Nutrition 0.000 claims description 7
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 6
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 4
- 239000004743 Polypropylene Substances 0.000 claims description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 4
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- 235000013772 propylene glycol Nutrition 0.000 claims description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 291
- 101710149632 Pectinesterase A Proteins 0.000 description 57
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000010410 layer Substances 0.000 description 23
- 239000002356 single layer Substances 0.000 description 23
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- 125000003118 aryl group Chemical group 0.000 description 15
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
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- 239000005977 Ethylene Chemical group 0.000 description 5
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- 230000000052 comparative effect Effects 0.000 description 5
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- 235000013305 food Nutrition 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002798 polar solvent Substances 0.000 description 5
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
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- 238000010438 heat treatment Methods 0.000 description 4
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
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- 239000013627 low molecular weight specie Substances 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
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- 150000004072 triols Chemical class 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
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- 239000004698 Polyethylene Substances 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
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- 125000002015 acyclic group Chemical group 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
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- 239000004715 ethylene vinyl alcohol Substances 0.000 description 1
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- STBLQDMGPBQTMI-UHFFFAOYSA-N heptane;isocyanic acid Chemical compound N=C=O.N=C=O.CCCCCCC STBLQDMGPBQTMI-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
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- 125000000962 organic group Chemical group 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
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- 229920001748 polybutylene Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
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- 239000000047 product Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
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- 239000000344 soap Substances 0.000 description 1
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- 238000003892 spreading Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
- 238000010408 sweeping Methods 0.000 description 1
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- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 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
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
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Classifications
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- 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
- C09J175/12—Polyurethanes from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/44—Polycarbonates
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- 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
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- 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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- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B27/08—Layered products comprising a layer of synthetic resin 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
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- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/32—Layered products comprising a layer of synthetic resin comprising polyolefins
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- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/36—Layered products comprising a layer of synthetic resin comprising polyesters
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- 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
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- 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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- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
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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
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3878—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus
- C08G18/3882—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus having phosphorus bound to oxygen only
- C08G18/3885—Phosphate compounds
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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
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
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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
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/46—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen
- C08G18/4615—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4829—Polyethers containing at least three hydroxy groups
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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
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
- C08G18/5036—Polyethers having heteroatoms other than oxygen having nitrogen containing -N-C=O groups
- C08G18/5045—Polyethers having heteroatoms other than oxygen having nitrogen containing -N-C=O groups containing urethane groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5075—Polyethers having heteroatoms other than oxygen having phosphorus
- C08G18/5081—Polyethers having heteroatoms other than oxygen having phosphorus having phosphorus bound to oxygen only
- C08G18/5084—Phosphate compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
- C08G18/6677—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203 having at least three hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
-
- 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
Definitions
- Laminates formed with solvent-based adhesives oftentimes exhibit poor adhesion after chemical aging and/or after high temperature testing such as a boil-in-bag test. Such laminates are unsuitable for laminate applications, such as food packaging and deep-drawn cans, which require sufficient adhesion for a period of time after exposure to heat and/or chemicals. Insufficient adhesion results in defects in the laminate structure, such as bubbling and delamination.
- the art recognizes the need for a solvent-based adhesive that exhibits sufficient adhesion between substrates after exposure to heat and/or chemicals. Further recognized in the art is the need for adhesive compositions that maintain adhesion in a laminate structure that is exposed to chemical aging, high temperature, and/or bag-in-boil testing.
- the present disclosure provides a two-component solvent-based adhesive composition.
- the two-component solvent-based adhesive composition contains the reaction product of (A) an isocyanate component; (B) a polyol component containing a polyester-amide polycarbonate polyol; and (C) a solvent.
- the present disclosure also provides a method of forming a two-component solvent-based adhesive composition.
- the method includes the steps of (A) providing a polyol component containing a polyester-amide polycarbonate polyol; (B) providing an isocyanate component; (C) providing a solvent; and (D) reacting the polyol component with the isocyanate component in the presence of the solvent to form the two-component solvent-based adhesive composition.
- the numerical ranges disclosed herein include all values from, and including, the lower and upper value.
- ranges containing explicit values e.g., a range from 1, or 2, or 3 to 5, or 6, or 7
- any subrange between any two explicit values is included (e.g., the range 1-7 above includes subranges 1 to 2; 2 to 6; 5 to 7; 3 to 7; 5 to 6; etc.).
- Alkyl refers to a saturated linear, cyclic, or branched hydrocarbon group.
- suitable alkyl groups include, for example, methyl, ethyl, n-propyl, i-propyl, n-butyl, t- butyl, i-butyl (or 2-methylpropyl), etc.
- the alkyls have 1 to 20 carbon atoms.
- Aryl refers to an aromatic substituent which may be a single aromatic ring or multiple aromatic rings which are fused together, linked covalently, or linked to a common group such as a methylene or ethylene moiety.
- the aromatic ring(s) may include phenyl, naphthyl, anthracenyl, and biphenyl, among others.
- aryls have from 1 to 200 carbon atoms, or from 1 to 50 carbon atoms, or from 1 to 20 carbon atoms.
- composition refers to a mixture of materials which comprise the composition, as well as reaction products and decomposition products formed from the materials of the composition.
- compositions claimed through use of the term “comprising” may include any additional additive, adjuvant, or compound, whether polymeric or otherwise, unless stated to the contrary.
- the term “consisting essentially of” excludes from the scope of any succeeding recitation any other component, step, or procedure, excepting those that are not essential to operability.
- the term “consisting of” excludes any component, step, or procedure not specifically delineated or listed.
- ether group is a moiety containing an oxygen atom bonded to two alkyl or aryl groups.
- substituted ether group refers to an ether in which one or more hydrogen atom bound to any carbon of the alkyl or aryl is replaced by another group such as a phosphate, a hydroxy, and combinations thereof.
- hydrocarbon is a compound that contains only hydrogen and carbon atoms.
- the hydrocarbon can be (i) branched or unbranched, (ii) saturated or unsaturated, (iii) cyclic or acyclic, and (iv) any combination of (i)-(iii).
- Nonlimiting examples of hydrocarbons include alkyls, aryls, alkanes, alkenes, and alkynes.
- An "isocyanate” is a compound that contains at least one isocyanate group in its structure.
- a "polyisocyanate” (or “multifunctional isocyanate”) is an isocyanate containing more than one, or at least two, isocyanate groups.
- a polyisocyanate having two isocyanate groups is a diisocyanate and an isocyanate having three isocyanate groups is a triisocyanate, etc.
- Isocyanates include aromatic isocyanates, aromatic polyisocyanates, aliphatic isocyanates and aliphatic polyisocyanates.
- a "polycarbonate” is a compound containing two or more carbonate groups in the same liner chain of atoms.
- a "polyester” is a compound containing two or more ester linkages in the same linear chain of atoms.
- a "polyester polyol” is a compound that is a polyester and a polyol.
- suitable polyester polyols include polycondensates of diols, polyols (e.g., triols, tetraols), dicarboxylic acids, polycarboxylic acids (e.g., tricarboxylic acids, tetracarboxylic acids), hydroxycarboxylic acids, lactones, and combinations thereof.
- the polyester polyols can also be derived from, instead of the free polycarboxylic acids, the corresponding polycarboxylic anhydrides, or corresponding polycarboxylic esters of lower alcohols.
- a "polymer” is a polymeric compound prepared by polymerizing monomers, whether of the same or a different type.
- the generic term polymer thus embraces the term “homopolymer” (employed to referto polymers prepared from only one type of monomer, with the understanding that trace amounts of impurities can be incorporated into the polymer structure), and the term “interpolymer,” which includes copolymers (employed to refer to polymers prepared from two different types of monomers), terpolymers (employed to refer to polymers prepared from three different types of monomers), and polymers prepared from more than three different types of monomers. Trace amounts of impurities, for example, catalyst residues, may be incorporated into and/or within the polymer.
- copolymer e.g., random, block, etc.
- a polymer is often referred to as being "made of” one or more specified monomers, "based on” a specified monomeror monomertype, "containing” a specified monomer content, or the like, in this context the term “monomer” is understood to be referring to the polymerized remnant of the specified monomer and not to the unpolymerized species.
- polymers herein are referred to has being based on “units” that are the polymerized form of a corresponding monomer.
- a "polyol” is an organic compound containing multiple hydroxyl (—OH) groups.
- a polyol contains at least two hydroxyl groups.
- suitable polyols include diols (which contain two hydroxyl groups) and triols (which contain three hydroxyl groups).
- Acid value is measured in accordance with ASTM D 1S86/7. Acid value is a measure of the amount of carboxylic acid present in a component or a composition. The acid value is the number of milligrams of potassium hydroxide required for the neutralization of free carboxylic acids present in one gram of a substance (e.g., a polyol). Units for acid value are mg KOH/g.
- Glass transition temperature is determined from the Differential Scanning Calorimetry (DSC) heating curve where half the sample has gained the liquid heat capacity, as described in Bernhard Wunderlich, The Basis of Thermal Analysis, in Thermal Characterization of Polymeric Materials 92, 278-279 (Edith A. Turi ed., 2d ed. 1997). Baselines are drawn from below and above the glass transition region and extrapolated through the Tg region. The temperature at which the sample heat capacity is half-way between these baselines is the Tg. The glass transition temperature is in degrees Celsius (°C).
- Hydroxyl number is a measure of the number of hydroxyl groups present in a component or a composition.
- the OH Number is the number of milligrams of potassium hydroxide required to neutralize the hydroxyl groups in one gram of a substance (mg KOH/g). The OH Number is determined in accordance with DIN 53240.
- Viscosity is measured at 25°C and 40°C in accordance with ASTM D2196. Viscosity is reported in mPa-s.
- Weight average molecular weight (Mw) and number average molecular weight (Mn) are measured using a gel permeation chromatography (GPC) system.
- the "Z average molecular weight"(Mz) is the third moment average molar mass. Mz is measured using a gel permeation chromatography (GPC) system.
- Mw, Mn, and Mz are calculated according to the following Equations (l)-(3):
- Equation (1) Equation (2) Equation (3) wherein Wfi is the weight fraction of the i-th component and Mi is the molecular weight of the i-th component.
- Polydispersity is calculated in accordance with the following Equation (4): Equation (4)
- W fj is the weight fraction of the j-th component with a molecular weight lower than 500 g/mol or 1,000 g/mol, respectively.
- Bond strength is measured in accordance with the 90° hand-assisted T-Peel Test.
- the laminate is cut into 2.54 cm wide strips after curing in an oven at 50°C for two days for the initial T-peel bond strength test.
- a Thwing AlbertTM QC-3A peel tester equipped with a 50 N loading cell is operated a rate of 10 inch/min. During testing, the tail of the strip is pulled slightly by finger to make sure the tail remains oriented at 90° to the peeling direction.
- the average bond strength (Newtons per 2.54 centimeter (N/2.54 cm)) is determined from the force versus distance profile. Three samples are tested and the average "bond strength" reported.
- Bond strength is measured within one hour of the formation of the laminate (i.e., initial or green bond strength), one day after the formation of the laminate, and seven days after the formation of the laminate. Bond strength is also measured after chemical aging and the boil-in-bag test, as described below.
- Laminates of 23 cm x 30.5 cm are folded onto themselves to provide a structure that is 23 cm x 15.3 cm, the structure having a first side and a second side.
- the first side and the second side each is formed from the same laminate.
- the second substrate (LDPE film or cast polypropylene film) of the first side is in contact with the second substrate (LDPE film or cast polypropylene film) of the second side.
- the structure has four edges, including a fold edge and three open edges. The edges are trimmed on a paper cutter to give a folded structure that is 12.7 cm x 17.8 cm. Two of the open edges are heat sealed to form a pouch. Heat sealing occurs at 177°C for 1 second at a hydraulic pressure of 276 kPa. Four to six pouches are made from each example.
- Each pouch is filled through the remaining open edge with 100 mL of a sauce (1:1:1 by weight mixture of ketchup, vinegar, and vegetable oil). Splashing the sauce onto a heat seal area is avoided to prevent heat seal failure. After filling, the open edge is heat sealed in a manner that minimizes air entrapment inside of the closed pouch.
- Each closed pouch has four closed edges and an interior void that is 10.2 cm x 15.2 cm (which is filled with sauce). The integrity of each heat seal is visually inspected to ensure there are no flaws in the sealing that would cause the pouch to leak during testing. Pouches with suspected flaws are discarded and replaced.
- a pot is filled 2/3 full with water, and brought to a rolling boil.
- the boiling pot is covered with a lid to minimize water and steam loss.
- the pot is observed during the test to ensure enough water is present to maintain boiling.
- Two to three pouches of each sample are individually placed in the boiling water, and kept in the boiling water for BO minutes.
- the pouches are then removed from the boiling water and visually inspected for tunneling, bubbling, blistering, delamination, and/or leakage.
- the pouches are cut open, emptied of sauce, and rinsed with soap and water.
- One or more strips (2.45 cm wide) of laminate are cut from the pouches (excluding heat seal areas). Bond strength of the laminate is measured in accordance with the 90° T-Peel Test as described above. Heat seal strength of the laminate is measured in accordance with the heat seal strength test described above. Bond strength and heat seal strength are measured as soon as possible after the pouches are emptied of soup. The interior of the pouches are visually inspected for defects
- the present disclosure provides a two-component solvent-based adhesive composition.
- the two-component solvent-based adhesive composition contains the reaction product of (A) an isocyanate component; (B) a polyol component containing a polyester-amide polycarbonate polyol; and (C) a solvent.
- the two-component solvent-based adhesive composition contains the reaction product of (A) an isocyanate component; (B) a polyol component; and (C) a solvent.
- Nonlimiting examples of suitable isocyanate components include aromatic isocyanates, aliphatic isocyanates, carbodiimide modified isocyanates, polyisocyanate trimers, polyfunctional isocyanate, isocyanate prepolymers, and the combinations thereof.
- aromatic isocyanate (or “aromatic polyisocyanate”) is an isocyanate containing one or more aromatic rings.
- suitable aromatic isocyanates include isomers of methylene diphenyl dipolyisocyanate (MDI) such as 4,4'-MDI, 2,4'-MDI, and 2, 2'- MDI; modified MDI such as carbodiimide modified MDI or allophanate modified MDI; isomers of toluene-dipolyisocyanate (TDI) such as 2,4-TDI, and 2,6-TDI; isomers of naphthalene- dipolyisocyanate (NDI) such as 1, 5-NDI; isomers of phenylene dipolyisocyanate (PDI), such as
- an "aliphatic isocyanate” is an isocyanate that is void of, or contains no, aromatic rings.
- Aliphatic isocyanates include cycloaliphatic isocyanate, in which the chemical chain is ring-structured.
- the aliphatic isocyanate contains from 3, or 4, or 5, or 6 to 7, or 8, 10, 12, or 13, or 14, or 15, or 16 carbon atoms in the linear, branched, or cyclic alkylene residue.
- Nonlimiting examples of suitable aliphatic isocyanates include cyclohexane diisocyanate; methylcyclohexane diisocyanate; ethylcyclohexane diisocyanate; propylcyclohexane diisocyanate; methyldiethylcyclohexane diisocyanate; propane diisocyanate; butane diisocyanate; pentane diisocyanate; hexane diisocyanate; heptane diisocyanate; octane diisocyanate; nonane diisocyanate; nonane triisocyanate; decane di- and tri-isocyanate; undecane di- and tri-isocyanate; dodecane di- and tri-isocyanate; isophorone diisocyanate; hexamethylene diisocyanate; diisocyanatodicyclohexylmethane; 2-methylpentane di
- a "polyisocyanate trimer” is the reaction product prepared by trimerization of di isocyanates in the presence of a catalyst.
- a nonlimiting example of a polyisocyanate trimer is
- the isocyanate is a polyfunctional isocyanate.
- the polyfunctional isocyanate is selected from a di-isocyanate, a tri-isocyanate, and combinations thereof.
- the polyfunctional isocyanate is a di isocyanate.
- An "isocyanate prepolymer” is the reaction product of a polyisocyanate and at least one polyol. The polyisocyanate bonds to a polyol in a chemical reaction to form the isocyanate prepolymer.
- suitable polyisocyanates include aromatic polyisocyanates, aliphatic polyisocyanates, carbodiimide modified polyisocyanates, and combinations thereof.
- suitable polyols used to form the isocyanate prepolymer include polyester polyols, polyether polyols, aliphatic polyols, and combinations thereof.
- the isocyanate prepolymer is the reaction product of a polyisocyanate, a polyol, and an optional catalyst.
- suitable catalysts include dibutyltin dilaurate, zinc acetate, 2, 2-dimorpholinodiethylether, and combinations thereof.
- the isocyanate is an aromatic isocyanate prepolymer.
- a nonlimiting example of a suitable aromatic isocyanate prepolymer is ADCOTETM 577, available from The Dow Chemical Company.
- the isocyanate component may comprise two or more embodiments disclosed herein.
- the two-component solvent-based adhesive composition contains the reaction product of (A) the isocyanate component; (B) a polyol component; and (C) a solvent.
- the polyol component contains a polyester-amide polycarbonate polyol.
- the polyol component contains (i) the polyester-amide polycarbonate and (ii) a phosphate-terminated polyol.
- the polyol component contains a polyester-polycarbonate polyol.
- a "polyester-amide polycarbonate polyol” is a compound that is a polyester, an amide, a polycarbonate, and a polyol.
- the PE-A PC can be prepared by reacting aliphatic and aromatic diacid monomer(s) (such as adipic acid (AA) and isophthalic acid), diol monomer(s) including aliphatic diol monomer and polyether diol monomer (such as ethylene glycol, 1,4- butanediol, 1,6-hexanediol (HDO), neopentyl glycol (NPG), and 1,2-propanediol (PDO)), a carbonate monomer or polycarbonate (such as poly(l,4-butanediol-carbonate (BDO-PC)), and an amide monomer (such as ethylenediamine (EDA)).
- aliphatic and aromatic diacid monomer(s) such as adipic acid (AA
- the PE-A PC is the reaction product of AA, PDO, NPG, HDO, BDO-PC, and EDA.
- the PE-A PC has the Structure (A):
- R 1 is selected from— (CH 2 )4— , Structure (X), and Structure (Y);
- R 2 is selected from— (CH 2 ) 4 — and— (CH2)6— ;
- R 3 is selected from— (CH 2 ) 2 — ,— (CH 2 ) 4 — ,— (CH 2 ) 6 — ,— (CH 2 ) 2 — O— (CH 2 ) 2 — ,— CH 2 — C(CH 3 )— , — GHz— CH(CH 3 )-CH 2 — , and -CH 2 -C(CH 3 ) 2 -CH 2 -;
- R 4 is selected from O, NH, NCH 3 , and NCH 2 CH 3 ;
- R 5 is selected from O, N H, NCH 3 , and NCH 2 CH 3 ; with the proviso that R 4 and R 5 are not both O.
- Structure (X) and Structure (Y) are as follows:
- the PE-A PC has a number average molecular weight, Mn, from 500 g/mol, or 1000 g/mol, or 1100 g/mol to 1700 g/mol, or 2000 g/mol, or 3000 g/mol, or 4000 g/mol, or 5000 g/mol, or 6000 g/mol, or 7000 g/mol, or 8000 g/mol.
- Mn number average molecular weight
- the PE-A PC has a weight average molecular weight, Mw, from 500 g/mol, or 1000 g/mol, or 2000 g/mol to 3000 g/mol, or 5000 g/mol. In another embodiment, the PE-A PC has a Mw from 500 g/mol to 5000 g/mol, or from 2000 g/mol to 3000 g/mol.
- the PE-A PC has a Mw/Mn from 1.5, or 1.6 to 1.9, or less than 2.0. In a further embodiment, the PE-A PC has a Mw/Mn from 1.5 to less than 2.0, or from 1.6 to 1.9. Not wishing to be bound by any particular theory, it is believed that a PE-A-PC with a Mw/Mn less than 2.0, in combination with a Mw greater than 500 g/mol, or greater than 2000 g/mol, minimizes the amount of migration of low molecular weight species in cured laminating adhesives, which is advantageous in food packaging applications.
- the PE-A PC has an acid value from 0.01 mg KOH/g to 1.0 mg KOH/g, or 2.0 mg KOH/g. In another embodiment, the PE-A PC has an acid value from 0.01 mg KOH/g to 2.0 mg KOH/g, or from 0.01 mg KOH/g to 1.0 mg KOH/g.
- the PE-A PC has an OH Number from 100 mg KOH/g, or 120 mg KOH/g to 150 mg KOH/g, or 175 mg KOH/g, or 200 mg KOH/g. In another embodiment, the PE-A PC has an OH Number from 100 mg KOH/g to 200 mg KOH/g, or from 100 mg KOH/g to 150 mg KOH/g, or from 120 mg KOH/g to 150 mg KOH/g.
- the PE-A PC has a glass transition temperature (Tg) from -90°C, or-85°C, or -80°C, or -75°C to -65°C, or -60°C, or -55°C, or -50°C.
- Tg glass transition temperature
- the PE-A PC has a Tg from -90°C to -50°C, or from -90°C to -60°C, or from -75°C to -60°C.
- the PE-A PC has a viscosity at 25°C from 500 mPa-s, or 1000 mPa-s, or 1500 mPa-s to 3000 mPa-s, or 5000 mPa-s, or 9000 mPa-s, or 10000 mPa-s. In another embodiment, the PE-A PC has a viscosity at 25°C from 500 mPa-s to 10000 mPa-s, or from 1500 mPa-s to 9000 mPa-s.
- the PE-A PC has a viscosity at 40°C from 500 mPa-s, or 700 mPa-s to 1000 mPa-s, or 3000 mPa-s, or 3500 mPa-s. In another embodiment, the PE-A PC has a viscosity at 40°C from 500 mPa-s to 3500 mPa-s, or from 700 mPa-s to 3000 mPa-s.
- the PE-A-PC with (i) a viscosity at 40°C of less than 3000 mPa-s and/or (ii) a viscosity at 25°C of less than 10000 mPa-s enables the two-component solvent-based adhesive composition to have a higher solids content (i.e., from 30 wt%, or 35 wt%, or 40 wt% to 45 wt%) than traditional solvent-based adhesive compositions, which is advantageous in solvent-based adhesive composition applications.
- the PE-A PC contains less than 55 wt%, or less than 50 wt%, or less than 40 wt%, or less than 30 wt%, or less than 20 wt%, or less than 15 wt%, or less than 10 wt% species having a Mw less than 500 g/mol, based on the total weight of the PE-A PC.
- the PE-A PC contains from 0 wt%, or 0.01 wt%, or 1 wt% to 10 wt%, or 15 wt%, or 20 wt%, or 30 wt%, or 40 wt%, or 50 wt%, or 55 wt% species having a Mw less than 500 g/mol, based on the total weight of the PE-A PC.
- the PE-A PC contains from 0 wt% to 10 wt% species having a Mw less than 500 g/mol, based on the total weight of the PE-A PC.
- the PE-A PC contains less than 55 wt%, or less than 50 wt%, or less than 40 wt%, or less than 30 wt%, or less than 27 wt% species having a Mw less than 1000 g/mol, based on the total weight of the PE-A PC.
- the PE-A PC contains from 0 wt%, or 0.01 wt%, or 1 wt% to 27 wt%, or 30 wt%, or 40 wt%, or 50 wt%, or 55 wt% species having a Mw less than 1000 g/mol, based on the total weight of the PE-A PC.
- the PE-A PC contains from 0 wt% to 30 wt% species having a Mw less than 1000 g/mol, based on the total weight of the PE-A PC.
- a low level i.e., less than 55 wt%) of species having a Mw less than 500 g/mol and/or (ii) a low level (i.e., less than 55 wt%) of species having a Mw less than 1000 g/mol in the PE-A-PC minimizes the amount of migration of low molecular weight species in cured laminating adhesives, which is advantageous in food packaging applications.
- the PE-A PC has one, some, or all of the following properties: (i) a Mn from 500 g/mol to 8000 g/mol, or from 1000 g/mol to 2000 g/mol; and/or (ii) a Mw from 500 g/mol to 5000 g/mol, or from 2000 g/mol to 3000 g/mol; and/or (iii) a Mw/Mn from 1.5 to less than 2.0, or from 1.6 to 1.9; and/or (iv) an acid value from 0.01 mg KOH/g to 2.0 mg KOH/g, or from 0.01 mg KOH/g to 1.0 mg KOH/g; and/or (v) an OH Number from 100 mg KOH/g to 200 mg KOH/g, or from 120 mg KOH/g to 150 mg KOH/g; and/or (vi) a Tg from -90°C to -50°C, or from -75°C to -60°C; and/or (vii) a Tg from
- the PE-A PC has one, some, or all of the properties (i)-(x), and the PE-A PC has the Structure (A).
- the PE-A PC is the reaction product of AA, PDO, NPG, HDO, BDO-PC, and EDA.
- the PE-A PC may comprise two or more embodiments disclosed herein.
- the polyol component may contain a phosphate-terminated polyol.
- a "phosphate-terminated polyol” (“PT-PO”) is a polyol containing at least one phosphate group having the Structure (B): Structure (B).
- the PT-PO may be prepared by reacting a polyether polyol with a phosphoric-type acid.
- a "phosphoric-type acid” is an orthophosphoric acid, a compound made by the condensation of orthophosphoric by the elimination of water, or a combination thereof.
- suitable phosphoric-type acid include pyrophosphoric acid, tripolyphosphoric acid, and polyphosphoric acid (PPA).
- the PT-PO is the reaction product of a polyether polyol and PPA.
- the PT-PO has the Structure (C): Structure (C)
- R 6 is an ether group or a substituted ether group.
- R 6 is a polyether. In another embodiment, R 6 contains only carbon atoms, hydrogen atoms, optional oxygen atoms, and optional phosphorous atoms.
- R 6 is selected from a C1-C120 ether group, or a C1-C50 ether group, or a C1-C24 ether group, or a Ci-Cs ether group, or a C1-C6 ether group, each of which may optionally contain one or more pendant—OH groups and/or one or more pendant Structure (B) groups.
- the PT-PO has an OH Numberfrom 50 mg KOH/g, or 100 mg KOH/g, or 110 mg KOH/g to 115 mg KOH/g, or 120 mg KOH/g, or 150 mg KOH/g. In another embodiment, the PT-PO has an OH Number from 50 mg KOH/g to 150 mg KOH/g, or from 100 mg KOH/g to 120 mg KOH/g.
- the PT-PO has an acid value from 5 mg KOH/g, or 10 mg KOH/g, or 15 mg KOH/g to 19 mg KOH/g, or 20 mg KOH/g, or 30 mg KOH/g, or 50 mg KOH/g. In another embodiment, the PT-PO has an acid value from 5 mg KOH/g to 50 mg KOH/g, orfrom 10 mg KOH/g to 20 mg KOH/g.
- the PT-PO has a viscosity at 25°C from 1000 mPa-s, or 1500 mPa-s, or 1600 mPa-s to 1700 mPa-s, or 1800 mPa-s, or 2000 mPa-s. In another embodiment, the PT-PO has a viscosity at 25°C from 1000 mPa-s to 2000 mPa-s, or from 1600 mPa-s to 1700 mPa-s.
- the PT-PO has a Mn from 500 g/mol, or lOOO g/mol, or 1500 g/mol, or 1700 g/mol to 1800 g/mol, or 2000 g/mol, or 3000 g/mol, or 4000 g/mol, or 5000 g/mol, or 6000 g/mol, or 7000 g/mol, or 8000 g/mol.
- the PT-PO has a Mn from 500 g/mol to 8000 g/mol, or from 1000 g/mol to 5000 g/mol, or from 1500 g/mol to 2000 g/mol.
- the PT-PO has a Mw from lOOOg/mol, or 2000 g/mol, or 3000 g/mol, or 4000 g/mol, or 4100 g/mol to 4200 g/mol, or 4500 g/mol, or 5000 g/mol, or 8000 g/mol, or 9000 g/mol, or 10000 g/mol.
- the PT-PO has a Mw from 1000 g/mol to 10000 g/mol, or from 2000 g/mol to 8000 g/mol, or from 2000 g/mol to 5000 g/mol, or from 4000 g/mol to 4500 g/mol.
- the PT-PO has a Mw/Mn from 1.5, or 2.0, or 2.2, or 2.4 to 2.5, or 2.6, or 2.8, or 3.0. In another embodiment, the PT-PO has a Mw/Mn from 1.5 to 3.0, or from 2.2 to 2.8.
- the PT-PO contains less than 20 wt%, or less than 15 wt%, or less than 10 wt%, or less than 8 wt%, or less than 5 wt% species having a Mw less than 500 g/mol, based on the total weight of the PT-PO.
- the PT-PO contains from 0 wt%, or 0.01 wt%, or 1 wt% to 4.5 wt%, or 5 wt%, or 8 wt%, or 10 wt%, or 15 wt%, or 20 wt% species having a Mw less than 500 g/mol, based on the total weight of the PT-PO.
- the PT- PO contains from 0 wt% to 5 wt% species having a Mw less than 500 g/mol, based on the total weight of the PT-PO.
- the PT-PO contains less than 40 wt%, or less than 35 wt%, or less than 30 wt%, or less than 25 wt%, or less than 20 wt% species having a Mw less than 500 g/mol, based on the total weight of the PT-PO.
- the PT-PO contains from 0 wt%, or 0.01 wt%, or 1 wt% to 16 wt%, or 20 wt%, or 25 wt%, or 30 wt%, or 35 wt%, or 40 wt% species having a Mw less than 1000 g/mol, based on the total weight of the PT-PO.
- the PT-PO contains from 0wt%to 20 wt% species having a Mw less than 1000 g/mol, based on the total weight of the PT-PO.
- a low level i.e., less than 20 wt%) of species having a Mw less than 500 g/mol and/or (ii) a low level (i.e., less than 40 wt%) of species having a Mw less than 1000 g/mol in the PT-PO minimizes the amount of migration of low molecular weight species in cured laminating adhesives, which is advantageous in food packaging applications.
- the PT-PO has one, some, or all of the following properties: (i) an OH Number from 50 mg KOH/g to 150 mg KOH/g, or from 100 mg KOH/g to 120 mg KOH/g; and/or (ii) an acid value from 5 mg KOH/g to 50 mg KOH/g, or from 15 mg KOH/g to 20 mg KOH/g; and/or (iii) a viscosity at 25°C from 1000 mPa-s to 2000 mPa-s, or from 1600 mPa-s to 1700 mPa-s; and/or (iv) a Mn from 500 g/mol to 8000 g/mol, or from 1600 g/mol to 1800 g/mol; and/or (v) a Mw from 1000 g/mol to 10000 g/mol, or from 4000 g/mol to 4500 g/mol; and/or (vi) a Mw/Mn from 1.5 to 3.0
- the PT-PO has one, some, or all of the properties (i)-(viii), and the PT-PO has the Structure (C).
- the PT-PO is the reaction product of a polyether polyol and PPA.
- a nonlimiting example of a suitable PT-PO is the PT-PO disclosed in U.S. Patent Publication No. 2017/0226391, the entire contents of which are herein incorporated by reference.
- the PT-PO may comprise two or more embodiments disclosed herein.
- the polyol component may contain (iii) an optional additive.
- suitable optional additives include polyols, adhesion promoters, chain extenders, catalysts, and combinations thereof.
- a nonlimiting example of a suitable optional additive is a polyol.
- the polyol may be any polyol disclosed herein, with the proviso that the optional polyol is different than (i) the PE- A PC and (ii) the PT-PO.
- the polyol may be compositionally distinct and/or physically distinct from (i) the PE-A PC and (ii) the PT-PO.
- Nonlimiting examples suitable polyols include diols (which contain two hydroxyl groups), triols (which contain three hydroxyl groups), and combinations thereof.
- suitable diols include 2-methyl-l, 3-propanediol (MPG); 3-methyl-l,5-pentanediol; ethylene glycol; butylene glycol; diethylene glycol (DEG); triethylene glycol; polyalkylene glycols, such as polyethylene glycol (PEG); 1, 2-propanediol; 1, 3-propanediol; 1, 3-butanediol; 1, 4- butanediol; 1, 6-hexanediol; and NPG.
- a nonlimiting example of a suitable triol is trimethylolpropane (TMP).
- the additive is a polyol that is a polyester polyol, a polyether polyol, or a combination thereof.
- suitable polyether polyols include polypropylene glycol, PEG, polybutylene glycol, polytetramethylene ether glycol, and combinations thereof.
- Nonlimiting examples of a suitable adhesion promoters include aminosilane (e.g., (3- aminopropyl)triethoxysilane and (3-aminopropyl)trimethoxysilane), epoxy silane (e.g., (3- glycidyloxypropyl)trimethoxysilane), phosphate ester (e.g., phosphate ester based on polypropylene glycol), epoxy resin (e.g., epoxy resin based on 1,4-butanediol diglycidyl ether), and combinations thereof.
- aminosilane e.g., (3- aminopropyl)triethoxysilane and (3-aminopropyl)trimethoxysilane
- epoxy silane e.g., (3- glycidyloxypropyl)trimethoxysilane
- phosphate ester e.g., phosphate ester based on polypropylene glycol
- epoxy resin e
- Nonlimiting examples of suitable chain extenders include glycerine; trimethylol propane; DEG; propanediol; MPG; 3-methyl-l, 5-pentanediol; and combinations thereof.
- Nonlimiting examples of suitable catalysts include tetra-n-butyl titanate, titanium isoproxide, zinc sulphate, organo tin catalyst (e.g., dibutyltin dilaurate), and combinations thereof.
- the reaction mixture excludes a chain extender.
- the optional additive may comprise two or more embodiments disclosed herein.
- the polyol component contains, consists essentially of, or consists of (i) the PE-A PC, (ii) optionally, the PT-PO, and (iii) optionally, an additive.
- the polyol component is a blend of (i) the PE-A PC, (ii) the PT-PO, and (iii) the optional additive.
- the polyol component contains from 65 wt%, or 70 wt%, or 75 wt%, or 79 wt%, or 80 wt%, or 85 wt%, or 90 wt% to 95 wt%, or 98 wt%, or 99 wt%, or 99.5 wt%, or 100 wt% PE-A PC, based on the total weight of the polyol component.
- the polyol component contains from 65 wt%, or 70 wt%, or 75 wt%, or 79 wt%, or 80 wt%, or 85 wt%, or 90 wt% to 95 wt%, or 98 wt%, or 99 wt%, or 99.5 wt% PE-A PC; and a reciprocal amount of PT-PO, or from 0.5 wt%, or 1 wt%, or 2 wt%, or 5 wt% to 10 wt%, or 15 wt%, or 20 wt%, or 21 wt%, or 25 wt%, or 30 wt%, or 35 wt% PT-PO, based on the total weight of the polyol component.
- the polyol component contains from 65 wt% to 99.5 wt%, or from 70 wt% to 99 wt%, or from 75 wt% to 95 wt%, or from 79 wt% to 95 wt% PE-A PC; and from 0.5 wt% to 35 wt%, or from 1 wt% to 30 wt%, or from 1 wt% to 25 wt%, or from 5 wt% to 21 wt% PT-PO, based on the total weight of the polyol component.
- the polyol component has an OH Numberfrom 50 mg KOH/g, or 100 mg KOH/g, or 120 mg KOH/g to 150 mg KOH/g, or 160 mg KOH/g, or 200 mg KOH/g. In another embodiment, the polyol component has an OH Number from 50 mg KOH/g to 200 mg KOH/g, or from 100 mg KOH/g to 150 mg KOH/g, or from 120 mg KOH/g to 150 mg KOH/g.
- the polyol component may comprise two or more embodiments disclosed herein.
- the two-component solvent-based adhesive composition contains the reaction product of (A) the isocyanate component; (B) the polyol component; and (C) a solvent.
- a “solvent” is a compound that is a liquid at 25°C, and is capable of providing a continuous medium in which each of the other components in the adhesive composition is dissolved and/or dispersed within.
- suitable solvents includes hydrocarbon solvents, polar solvents, and combinations thereof.
- hydrocarbon solvent contains only hydrogen and carbon atoms, including branched or unbranched, saturated or unsaturated, cyclic, polycyclic or acyclic species, and combinations thereof.
- the hydrocarbon solvent is selected from aromatic hydrocarbon solvents, aliphatic hydrocarbon solvents, and combinations thereof.
- aromatic hydrocarbon is a hydrocarbon that contains one or more benzene rings.
- aromatic hydrocarbon solvents include toluene and xylene.
- the hydrocarbon solvent is an aromatic hydrocarbon solvent that is toluene.
- An "aliphatic hydrocarbon” is a hydrocarbon that is an alkane, an alkene, an alkyne, or a derivative of an alkane, an alkene or an alkyne.
- Nonlimiting examples of aliphatic hydrocarbon solvents include hexene, cyclohexane and methylcyclohexane (MCH).
- a "polar solvent” is a substance capable of dissolving another substance (solute) to form a uniformly dispersed mixture (solution) at the molecular or ionic level; the solvent composed of molecules in which positive and negative electrical charges are permanently separated, as opposed to nonpolar molecules in which the charges coincide.
- polar solvents include alcohols, ketones and esters.
- the polar solvent is a ketone.
- suitable ketones include acetone, methyl ethyl ketone and cyclohexanone.
- the polar solvent is an ester.
- suitable esters include butyl acetate and ethyl acetate.
- the solvent is selected from ethyl acetate, methyl ethyl ketone, and combinations thereof. In a further embodiment, the solvent is ethyl acetate.
- the solvent may comprise two or more embodiments disclosed herein.
- the two-component solvent-based adhesive composition contains the reaction product of (A) the isocyanate component; (B) the polyol component containing (i) the PE-A PC and (ii) optionally, the PT-PO; and (C) the solvent.
- the two-component solvent-based adhesive composition is formed by mixing (A) the isocyanate component, (B) the polyol component, and (C) the solvent under conditions suitable to react the— NCO groups of the isocyanate component with the hydroxyl groups of the polyol component.
- (A) the isocyanate component, (B) the polyol component, and (C) the solvent are combined and mixed at a temperature from 15°C, or 20°C to 23°C, or 25°C, or 45°C for a period from 10 minutes to 30 minutes.
- (A) the isocyanate component, (B) the polyol component are completely dissolved, or substantially dissolved, in (C) the solvent.
- the (C) solvent may be pre-mixed with the (A) isocyanate component and/or the (B) polyol component.
- the (C) solvent is pre-mixed with the (B) polyol component.
- the polyol component is mixed with solvent before it contacts the isocyanate component.
- the (C) solvent is pre-mixed with the (B) polyol component, and the pre-mix has a solids content from 25 wt%, or 50 wt%, or 70 wt%, or 75 wt% to 80 wt%, or 90 wt%, or 95 wt%, or 99 wt%.
- the two-component solvent-based adhesive composition includes (A) isocyanate component and (B) polyol component at an lsocyanate:Polyol Weight Ratio, based on dry weight, from 100:1, or 100:12, or 100:13 to 100:17, or 100:20.
- the two-component solvent-based adhesive composition includes (A) isocyanate component and (B) polyol component at an lsocyanate:Polyol Weight Ratio, based on dry weight, from 100:1 to 100:20, or from 100:12 to 100:17, or from 100:13 to 100:17.
- the two-component solvent-based adhesive composition contains from 55 wt% to 60 wt%, or 65 wt%, or 70 wt% solvent, based on the total weight of the two- component solvent-based adhesive composition.
- the two-component solvent-based adhesive composition has a solids content from 30 wt%, or 35 wt%, or 40 wt% to 45 wt%, based on the total weight of the two- component solvent-based adhesive composition. In another embodiment, the two-component solvent-based adhesive composition has a solids content from 30 wt% to 45 wt%, or from 40 wt% to 45 wt%, based on the total weight of the two-component solvent-based adhesive composition.
- the two-component solvent-based adhesive composition contains, consists essentially of, or consists of, the reaction product of
- the PE-A PC having one, some, or all of the following properties: (a) a Mn from 500 g/mol to 8000 g/mol, or from 1000 g/mol to 2000 g/mol; and/or (b) a Mw from 500 g/mol to 5000 g/mol, or from 2000 g/mol to 3000 g/mol; and/or (c) a Mw/Mn from 1.5 to less than 2.0, or from 1.6 to 1.9; and/or (d) an acid value from 0.01 mg KOH/g to 2.0 mg KOH/g, or from 0.01 mg KOH/g to 1.0 mg KOH/g; and/
- the PT- PO having one, some all of the following properties: (a) an OH Number from 50 mg KOH/g to 150 mg KOH/g, or from 100 mg KOH/g to 120 mg KOH/g; and/or (b) an acid value from 5 mg KOH/g to 50 mg KOH/g, or from 15 mg KOH/g to 20 mg KOH/g; and/or (c) a viscosity at 25°Cfrom 1000 mPa-s to 2000 mPa-s, or from 1600 mPa-s to 1700 mPa-s; and/or (d) a Mn from 500 g/mol to 8000 g/mol, or from 1600 g/mol to 1800
- the polyol component has an OH Number from 50 mg KOH/g to 200 mg KOH/g, or from 100 mg KOH/g to 150 mg KOH/g, or from 120 mg KOH/g to 150 mg KOH/g;
- composition has one, some, or all of the following properties: (a) a solids content from BO wt% to 45 wt%, or from 40 wt% to 45 wt%, based on the total weight of the two- component solvent-based adhesive composition; and/or (b) an lsocyanate:Polyol Weight Ratio, based on dry weight, from 100:1 to 100:20, or from 100:12 to 100:17, or from 100:13 to 100:17.
- the two-component solvent-based adhesive composition may comprise two or more embodiments disclosed herein.
- the present disclosure provides a laminate.
- the laminate includes a first substrate, a second substrate, and an adhesive layer between the first substrate and the second substrate.
- the adhesive layer is formed from the two-component solvent-based adhesive composition.
- the two-component solvent-based adhesive composition may be any two-component solvent-based adhesive composition disclosed herein.
- the laminate includes a first substrate and a second substrate.
- the first substrate and the second substrate may be the same or different.
- the first substrate and the second substrate are the same, such that they have the identical compositions and identical structures.
- the first substrate and the second substrate are compositionally distinct and/or structurally distinct from one another.
- substrate refers to the first substrate and the second substrate, individually and/or collectively.
- a nonlimiting example of a suitable substrate is a film.
- the film may be a monolayer film or a multilayer film.
- the multilayer film contains two layers, or more than two layers.
- the multilayer film can have two, three, four, five, six, seven, eight, nine, ten, eleven, or more layers.
- the multilayer film contains only two layers, or only three layers.
- the film is a monolayer film with one, and only one, layer.
- the film includes a layer containing a component selected from ethylene-based polymer, propylene-based polymer (PP), polyamide (such as nylon), polyester, ethylene vinyl alcohol (EVOH) copolymer, polyethylene terephthalate (PET), ethylene vinyl acrylate (EVA) copolymer, ethylene methyl acrylate copolymer, ethylene ethyl acrylate copolymer, ethylene butyl acrylate copolymer, ethylene acrylic acid copolymer, ethylene methacrylic acid copolymer, an ionomer of ethylene acrylic acid, an ionomer of methacylic acid, maleic anhydride grafted ethylene- based polymer, a polylactic acid (PLA), a polystyrene, a metal foil, a cellulose, cellophane, nonwoven fabric, and combinations thereof.
- a nonlimiting example of a suitable metal foil is aluminum foil.
- Each layer of a multilayer film may for formed from ethylene vinyl
- the film includes a layer containing metal foil.
- the film is a monolayer film having a single layer that is an ethylene- based polymer layer. In a further embodiment, the film is a monolayer film having a single layer that is a polyethylene layer.
- the substrate, and further the film, is a continuous structure with two opposing surfaces.
- the substrate has a thickness from 5 pm, or 10 pm, or 15 pm, or 20 pm to 25 pm, or 30 pm, or 40 pm, or 50 pm, or 100 pm, or 200 pm, or 300 pm, , or 400 pm, or 500 pm .
- the first substrate is a film having a layerthat is a metal foil layer; and the second substrate is a monolayer film having a single layer that is an ethylene-based polymer layer (such as low density polyethylene (LDPE)) or a propylene-based polymer layer (such as polypropylene).
- LDPE low density polyethylene
- propylene-based polymer layer such as polypropylene
- the first substrate may comprise two or more embodiments disclosed herein.
- the second substrate may comprise two or more embodiments disclosed herein.
- the two-component solvent-based adhesive composition is applied between the first substrate and the second substrate, such as with a Nordmeccanica Labo Combi laminator.
- Nonlimiting examples of suitable application methods include brushing, pouring, spraying, coating, rolling, spreading, and injecting.
- the two-component solvent-based adhesive composition is applied between the first substrate and the second substrate at a coat weight from 3 grams per square meter (g/m 2 ) to 4 g/m 2 .
- the two-component solvent-based adhesive composition is uniformly applied between on first substrate, the solvent is evaporated to form an adhesive layer, and then the adhesive layer is brought into contact with the second substrate.
- a "uniform application” is a layer of the composition that is continuous (not intermittent) across a surface of the substrate, and of the same, or substantially the same, thickness across the surface of the substrate. In other words, a composition that is uniformly applied to a substrate directly contacts the substrate surface, and the composition is coextensive with the substrate surface.
- the two-component solvent-based adhesive composition and the first substrate are in direct contact with each other.
- the term "directly contacts,” as used herein, is a layer configuration whereby a substrate is located immediately adjacent to a two-component solvent-based adhesive composition, or an adhesive layer and no intervening layers, or no intervening structures, are present between the substrate and the two-component solvent-based adhesive composition, or the an adhesive layer.
- the two-component solvent-based adhesive composition directly contacts a surface of the first substrate.
- the structure containing the first substrate and the two- component solvent-based adhesive composition has the following Structure (D):
- the Structure (D) is dried to form an adhesive layer in direct contact with the first substrate.
- the Structure (D) is dried by passing it through an oven at a temperature sufficient to evaporate all, or substantially all, of the solvent from the two- component solvent-based adhesive composition. Then, the adhesive layer is contacted with the second substrate to form a laminate.
- the laminate has the following Structure (E):
- the adhesive layer and the second substrate are in direct contact with each other.
- the adhesive layer directly contacts a surface of the second substrate.
- the adhesive layer of Structure (E) is formed from curing, or drying the two-component solvent-based adhesive composition.
- the two-component solvent-based adhesive composition is formed from mixing and reacting the (A) isocyanate component and the (B) polyol component in the presence of (C) a solvent.
- the laminate includes the first substrate in direct contact with the adhesive layer, and the second substrate in direct contact with the adhesive layer.
- the first substrate is a film having a layer that is a metal foil layer
- the second substrate is a monolayer film having a single layer that is an ethylene-based polymer (such as LDPE)
- the laminate has one, some, or all of the following properties: (i) an initial bond strength (green bond) from 1.5 N/2.54 cm, or 1.7 N/2.54 cm to 4.0 N/2.54 cm, or 5.0 N/2.54 cm; and/or (ii) a bond strength after one day from 5.0 N/2.54 cm to 17.0 N/2.54 cm, or 20.0 N/2.54 cm; and/or (iii) a bond strength after seven days from 7.5 N/2.54 cm to 16.0 N/2.54 cm, or 20.0 N/2.54 cm; and/or (iv) a bond strength after the boil-in-bag test from 8.73 N/2.54 cm, or 8.75 N/2.54 cm to 15.50 N/2.54 cm, or 16.00 N/2.54 cm, or 20
- the first substrate is a film having a layerthat is a metal foil layer
- the second substrate is a monolayer film having a single layer that is a propylene-based polymer (such as polypropylene, or further a cast polypropylene)
- the laminate has one, some, or all of the following properties: (i) an initial bond strength (green bond) from 1.5 N/2.54 cm to 6.0 N/2.54 cm, or 7.0 N/2.54 cm; and/or (ii) a bond strength after one day from 10.0 N/2.54 cm, or 12.0 N/2.54 cm to 16.0 N/2.54 cm, or 20.0 N/2.54 cm; and/or (iii) a bond strength after seven days from 12.0 N/2.54 cm to 16.0 N/2.54 cm, orl8.0 N/2.54 cm; and/or (iv) a bond strength after the boil-in-bag test from 7.5 N/2.54 cm to 13.0 N/2.54 cm, or 15.0 N/2.54
- the first substrate is a monolayer film having a single layer that is PET
- the second substrate is a monolayer film having a single layer that is an ethylene-based polymer (such as LDPE)
- the laminate has one, some, or all of the following properties: (i) an initial bond strength (green bond) from 0.5 N/2.54 cm to 4.0 N/2.54 cm, or 50.0 N/2.54 cm; and/or (ii) a bond strength after one day from 12.0 N/2.54 cm to 23.0 N/2.54 cm, or 25.0 N/2.54 cm or 30.0 N/2.54 cm; and/or (iii) a bond strength after seven days from 14.0 N/2.54 cm, to 22.0 N/2.54 cm, or 25.0 N/2.54 cm; and/or (iv) a bond strength after the boil-in-bag test from 3.0 N/2.54 cm, or 3.5 N/2.54 cm to 6.0 N/2.54 cm, or 8.0 N/2.54 cm, or
- the first substrate is a monolayer film having a single layer that is PET
- the second substrate is a monolayer film having a single layer that is a propylene-based polymer (such as polypropylene, or further a cast polypropylene)
- the laminate has one, some, or all of the following properties: (i) an initial bond strength (green bond) from 0.2 N/2.54 cm to 4.0 N/2.54 cm, or 5.0 N/2.54 cm, or 10.0 N/2.54 cm; and/or (ii) a bond strength after one day from 10.0 N/2.54 cm, or 11.0 N/2.54 cm to 18.0 N/2.54 cm, or 20.0 N/2.54 cm; or from 10.0 N/2.54 cm to 20.0 N/2.54 cm, or from 11.0 N/2.54 cm to 18.0 N/2.54 cm; and/or (iii) a bond strength after seven days from 13.5 N/2.54 cm to 25.0 N/2.54 cm, or 30.0 N/2.54
- the laminate may comprise two or more embodiments disclosed herein.
- the present disclosure also provides a method of forming the two-component solvent- based adhesive composition.
- the method includes (A) providing a polyol component containing a polyester-amide polycarbonate polyol (PE-A PC); (B) providing an isocyanate component; (C) providing a solvent; and (D) reacting the polyol component with the isocyanate component in the presence of the solvent to form the two-component solvent-based adhesive composition.
- PE-A PC polyester-amide polycarbonate polyol
- the polyol component, the PE-A PC, the isocyanate component, and the two-component solvent-based adhesive composition may be any respective polyol component, PE-A PC, isocyanate component, and two-component solvent-based adhesive composition disclosed herein.
- the process includes forming the polyol component by mixing the PE-A PC with a PT-PO.
- the method may comprise two or more embodiments disclosed herein.
- the present disclosure also provides an article containing the laminate.
- suitable articles include packages, bags, pouches, deep-drawn cans, and containers.
- the laminate contacts a comestible.
- a "comestible” is an edible food item.
- a BO gallon 316Lstainless steel vessel having an internal diameter of 20 inches is equipped with internal baffles, a variable speed 12-inch turbine impeller, a sparge ring, a closed loop system with a mixed DOWTHERMTM system having independent hot and cold loops and a 24-inch packed column.
- BDO 1,4-butanediol
- TYZORTM TPT catalyst (21.6 g) is added and the line is flushed with 600.0 g BDO previously purged from the reactor.
- Dimethyl carbonate (DMC) (102864.0 g) is added from a weight pot using a flow meter and control valve over a period of 6 to 8 hrs, while maintaining the temperature in the column at 65°C.
- DMC Dimethyl carbonate
- the temperature is increased to 195°C, and the progress of the reaction is tracked by OH number and 1 H-NMR for end-group analysis. After 8 hrs at 195°C, the OH number is found to be 30.7 with 25% carbonate end-groups by 1 H-NMR.
- the temperature is decreased to 150°C and 4.1 pounds (lbs) of BDO is added to the reaction.
- a poly(l,4-butanediol-carbonate) (BDO-PC) is prepared that has an OH number of 54 mg KOH/g and a Mn of 1960 g/mol.
- Polyester-amide polycarbonate polyols are synthesized according to the following general procedure, with detailed formulation compositions for each sample provided in Table 2.
- the reaction is run in a glass reactor with a 1000 mL three neck flask equipped with a thermocouple inlet port.
- One neck of the reactor contains a gas inlet adapter that contains a 29/42 neck with a stopper attached.
- the gas inlet is fed with nitrogen regulated by an adjustable flow meter.
- the second neck of the reactor contains a custom mechanical stirring shaft adapter modified to allow for a vacuum use.
- the third neck of the reactor contains an offset adapter attached to a 12-inch long column leading to distillation head and a condenser with a three neck bottom drain collection flask at a bottom of condenser.
- the collection flask has one line leading to a J-KEMTM vacuum regulator, and another line leading to a nitrogen bubbler.
- the 12-inch column off of the offset adapter is packed with 5 mm glass beads.
- the column is heated by way of a heating tape controlled by a variac with a thermocouple monitoring column surface temperature. Heating for the reactor is supplied by a heating mantle fed from a control box with over-temp shut off. Mechanical stirring is achieved using a custom 1/4 inch stainless steel paddle and shaft.
- the reactor is charged with 1,6-hexanediol (HDO), neopentyl glycol (NPG), 1,2-propanediol (PDO), and amine monomer.
- the mixture is vacuum degassed and nitrogen purged up to three times, and then slowly heated to less than 100°C. Adipic acid is added and the mixture and allowed to stir for approximately one hour.
- the temperature is then increased to 150°C and titanium isopropoxide (supplied by Aldrich) is injected.
- the temperature of the reaction is raised incrementally, as distillate begins to slow, up to 210°C.
- Moderate vacuum pressure is applied to drive the reaction to completion.
- the acid value is monitored to determine the end-point of the reaction. When the acid value is lower than 1.0, the polyester component is deemed complete.
- the BDO-PC prepared as described above and 1,6-hexanediol (HDO) (equimolar to BDO-PC) are added to the polyester component, at room temperature, and the solution is heated to 210°C for four hours.
- a 1 liter multi-neck round bottom flask is dried in an oven, flushed with dry nitrogen for 30 minutes, and then charged with 150 grams of VORANOLTM CP 450 (polyether polyol) and is placed under an ISh sweep of 70 mL/min.
- a syringe is loaded with 4 grams of 115% polyphosphoric acid (PPA) (supplied by Sigma Aldrich).
- PPA polyphosphoric acid
- the PPA is added dropwise to the VORANOLTM CP 450 with strong agitation. A minimal temperature increase is observed.
- the reactor contents are heated to 100°C for 1 hour, and are then cooled to 45°C. 40 grams of ethyl acetate is added, followed by the slow addition of 50 grams of ISONATETM 125M (MDI blend).
- the prepared phosphate-terminated polyol does not contain excess, or free, MDI.
- the PT-PO has a solids content of 76 wt%, an OH Numberof 112 mg KOH/g, an acid value of 19.0 mg KOH/g, a viscosity at 25°C of 1665 mPa-s, a Mn of 1700 g/mol, a Mw of 4100 g/mol, and a Mw/Mn of 2.4.
- the PT-PO contains 4.4 wt% species with a Mw less than 500 g/mol, and 16.0 wt% species with a Mw less than 1000 g/mol.
- wt% in Table 3 is based on the total weight of the respective Polyol Component (PC)
- Two-component solvent-based adhesive compositions are prepared by mixing (A) ADCOTETM 577 (aromatic isocyanate prepolymer) with (B) one of the Ex PC 1-7, CS PC 8-9, ADCOTETM 577B (a hydroxyl-terminated polyol composition), ADCOTETM L87-124 (a hydroxyl- terminated polyol composition), orCR86-139 (a hydroxyl-terminated polyol composition), and (C) ethyl acetate, in a kettle at room temperature (23°C) until a homogeneous mixture is achieved, forming a two-component solvent-based adhesive composition.
- the components of each example and comparative example adhesive composition are provided in Tables 4 and 5.
- a low density polyethylene (LDPE) film containing a slip agent that is a monolayer film having a thickness of 1.5 mils is provided (GF-19, available from Berry Plastics Corp.).
- a cast polypropylene film that is a monolayer film having a thickness of 3 mil is provided.
- a polyethylene glycol-terephthalate) (PET) film that is a monolayer film having a thickness of 1 mil (24.5 pm) is provided (92LBT, available from DuPont).
- a metal foil film is provided (aluminum foil).
- the metal foil film is a monolayerfilm having a thickness of 1.5 mils (38.1 pm).
- the metal foil film is pre-laminated with a PET film (having a thickness of 12 pm, 48 gauge) using ADCOTETM 577 : Coreactant F (a solvent-based, 2-component polyurethane adhesive, commercially available from The Dow Chemical Company) at a coat weight of 3.26 g/m 2 (2.00 Ibs/ream) to form a Metal Foil Pre-Laminate (Prelam) having the following Structure (I):
- the example and comparative example adhesive compositions are loaded into a Nordmeccanica SDC Labo Combi pilot laminator.
- the laminator nip temperature is maintained at 60°C
- the oven temperature is set at 80°C for each zone
- the laminator is operated at a speed of 30 meters per minute (m/min).
- Each example and comparative example adhesive composition is maintained at the solids content of Tables 4 and 5 during lamination.
- the adhesive composition is applied to eitherthe Metal Foil Pre-Laminate (Prelam) orthe PET film (92LBT), to form the following Structure (II) and Structure (III):
- the adhesive composition directly contacts the surface of the metal foil film layer of the Metal Foil Pre-Laminate (having the Structure (I)).
- the Structure (II) and the Structure (III) is cured in a controlled room at a temperature of 25°C and a relative humidity of 50% for a period of 7-14 days to evaporate all, or substantially all, of the solvent and form an adhesive layer.
- the LDPE film or the cast polypropylene film is brought into contact with the adhesive layer to form a laminate having the Structure (IV), the Structure (V), the Structure (VI), or the Structure (VII):
- CS 8-12 each includes an adhesive layer formed from (A) an isocyanate component (ADCOTETM 577), (B) a polyol component (ADCOTETM 577B, CR86-139, ADCOTETM L87-124, CS PC 8, and CS PC 9, respectively) that lacks a polyester-amide polycarbonate polyol (PE-A PC), and (C) a solvent (ethyl acetate).
- the laminate structures of CS 8-12 that have the Structure (IV) i.e., Prelam / Adhesive Composition / LDPE
- CS 8-12 each exhibits insufficient bond strength after the boil-in-bag test.
- Ex 1-7 each includes an adhesive layerformed from (A) an isocyanate component (ADCOTETM 577), (B) a polyol component (PC 1-7, respectively) containing PE-A PC, and (C) a solvent (ethyl acetate).
- the laminate structures of Ex 1-7 that have the Structure (IV) i.e., Prelam / Adhesive Composition / LDPE
- Ex 1-7 each exhibits sufficient bond strength after the boil-in- bag test.
- CS 8-12 each includes an adhesive layer formed from (A) an isocyanate component (ADCOTETM 577), (B) a polyol component (ADCOTETM 577B, CR86-139, ADCOTETM L87-124, CS PC 8, and CS PC 9, respectively) that lacks a PE-A PC, and (C) a solvent (ethyl acetate).
- the laminate structures of CS 8-12 that have the Structure (VII) i.e., PET / Adhesive Composition / Cast Polypropylene
- CS 8-12 each exhibits insufficient bond strength after one day.
- Ex 1-7 each includes an adhesive layerformed from (A) an isocyanate component (ADCOTETM 577), (B) a polyol component (PC 1-7, respectively) containing PE-A PC, and (C) a solvent (ethyl acetate).
- the laminate structures of Ex 1-7 that have the Structure (VII) i.e., PET / Adhesive Composition / Cast Polypropylene
- Ex 1-7 each exhibits sufficient bond strength after one day.
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Abstract
Description
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EP20714809.9A EP3934909A1 (en) | 2019-03-05 | 2020-03-04 | Two-component solvent-based adhesive composition |
CN202080025458.6A CN113646169B (en) | 2019-03-05 | 2020-03-04 | 2 Component solvent-based adhesive composition |
MX2021010708A MX2021010708A (en) | 2019-03-05 | 2020-03-04 | Two-component solvent-based adhesive composition. |
JP2021552800A JP7473561B2 (en) | 2019-03-05 | 2020-03-04 | Two-component solvent-based adhesive composition |
BR112021017607A BR112021017607A2 (en) | 2019-03-05 | 2020-03-04 | Two-component solvent-based adhesive composition, laminate, and method for forming a two-component solvent-based adhesive composition |
US17/436,515 US11746267B2 (en) | 2019-03-05 | 2020-03-04 | Two-component solvent-based adhesive composition |
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US201962813857P | 2019-03-05 | 2019-03-05 | |
US62/813,857 | 2019-03-05 |
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US (1) | US11746267B2 (en) |
EP (1) | EP3934909A1 (en) |
JP (1) | JP7473561B2 (en) |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2021247160A1 (en) * | 2020-06-03 | 2021-12-09 | Dow Global Technologies Llc | Solvent-based laminating adhesive |
WO2022082576A1 (en) * | 2020-10-22 | 2022-04-28 | Dow Global Technologies Llc | Isocyanate compounds and adhesive compositions comprising the same |
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TW202033592A (en) * | 2019-03-05 | 2020-09-16 | 美商陶氏全球科技有限責任公司 | Two-component solvent-based adhesive composition |
AR118229A1 (en) | 2019-03-05 | 2021-09-22 | Dow Global Technologies Llc | ADHESIVE COMPOSITION OF TWO COMPONENTS WITHOUT SOLVENTS |
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Also Published As
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US11746267B2 (en) | 2023-09-05 |
BR112021017607A2 (en) | 2021-11-16 |
JP2022524029A (en) | 2022-04-27 |
CN113646169A (en) | 2021-11-12 |
TW202033593A (en) | 2020-09-16 |
EP3934909A1 (en) | 2022-01-12 |
CN113646169B (en) | 2024-05-24 |
AR118237A1 (en) | 2021-09-22 |
JP7473561B2 (en) | 2024-04-23 |
MX2021010708A (en) | 2021-12-10 |
US20220186098A1 (en) | 2022-06-16 |
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