WO2013084891A1 - 湿気硬化型ホットメルト接着剤 - Google Patents
湿気硬化型ホットメルト接着剤 Download PDFInfo
- Publication number
- WO2013084891A1 WO2013084891A1 PCT/JP2012/081389 JP2012081389W WO2013084891A1 WO 2013084891 A1 WO2013084891 A1 WO 2013084891A1 JP 2012081389 W JP2012081389 W JP 2012081389W WO 2013084891 A1 WO2013084891 A1 WO 2013084891A1
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- WO
- WIPO (PCT)
- Prior art keywords
- moisture
- hot melt
- melt adhesive
- curable hot
- polyol
- Prior art date
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- 239000004831 Hot glue Substances 0.000 title claims abstract description 83
- 229920005862 polyol Polymers 0.000 claims abstract description 58
- 150000003077 polyols Chemical class 0.000 claims abstract description 55
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- 239000004417 polycarbonate Substances 0.000 claims abstract description 31
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 229920000058 polyacrylate Chemical group 0.000 claims abstract description 26
- 239000000126 substance Substances 0.000 claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 claims abstract description 14
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000463 material Substances 0.000 claims description 30
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 20
- 229920000642 polymer Polymers 0.000 claims description 9
- 239000000853 adhesive Substances 0.000 abstract description 15
- 230000001070 adhesive effect Effects 0.000 abstract description 15
- -1 isocyanate compound Chemical class 0.000 description 46
- 239000012948 isocyanate Substances 0.000 description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 20
- 238000012360 testing method Methods 0.000 description 20
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- 238000013008 moisture curing Methods 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- OJRJDENLRJHEJO-UHFFFAOYSA-N 2,4-diethylpentane-1,5-diol Chemical compound CCC(CO)CC(CC)CO OJRJDENLRJHEJO-UHFFFAOYSA-N 0.000 description 8
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- 238000002844 melting Methods 0.000 description 8
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- 239000011347 resin Substances 0.000 description 8
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- 238000012423 maintenance Methods 0.000 description 6
- 229920000139 polyethylene terephthalate Polymers 0.000 description 6
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- 229920005992 thermoplastic resin Polymers 0.000 description 4
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
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- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 3
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- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
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- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
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- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
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- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- ACYQDCZIQOLHRX-UHFFFAOYSA-M dodecanoate;trimethylstannanylium Chemical compound CCCCCCCCCCCC(=O)O[Sn](C)(C)C ACYQDCZIQOLHRX-UHFFFAOYSA-M 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 235000019808 microcrystalline wax Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- TXXWBTOATXBWDR-UHFFFAOYSA-N n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCN(C)C TXXWBTOATXBWDR-UHFFFAOYSA-N 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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
- 238000012546 transfer Methods 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/08—Polyurethanes from polyethers
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4063—Mixtures of compounds of group C08G18/62 with other macromolecular 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
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
- C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
- C08G18/4211—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic 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
- C08G18/44—Polycarbonates
-
- 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
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
- C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
-
- 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
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7628—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group
- C08G18/7642—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group containing at least two isocyanate or isothiocyanate groups linked to the aromatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate groups, e.g. xylylene diisocyanate or homologues substituted on the aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/062—Copolymers with monomers not covered by C08L33/06
- C08L33/066—Copolymers with monomers not covered by C08L33/06 containing -OH groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/08—Homopolymers or copolymers of acrylic acid esters
-
- 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
- C08G2170/00—Compositions for adhesives
- C08G2170/20—Compositions for hot melt adhesives
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
Definitions
- the present invention relates to a moisture curable hot melt adhesive.
- the present invention relates to a moisture curable hot melt adhesive that is excellent in light resistance and durability, and is particularly suitable for automobile interior use.
- Patent Document 1 discloses that a reactive (moisture curable) hot melt adhesive obtained by a reaction between a polycarbonate-based polyol and a polyisocyanate has improved initial adhesive strength and heat-resistant adhesive strength, and has heat stability and moisture resistance (or water resistance). ) Is disclosed (see Examples in Patent Document 1).
- Patent Document 2 and Patent Document 3 a reactive (moisture-curable) hot melt composition is produced by reacting a mixed polyol of polycarbonate polyol and polyester polyol with polyisocyanate (Examples of Patent Documents 2 and 3). See).
- the polycarbonate polyol is a known polyol for producing a moisture curable hot melt adhesive.
- moisture-curable hot melt adhesives are required not only to have initial adhesive strength but also to be excellent in weather resistance, and in recent years, in particular, it is important to be excellent in light resistance among weather resistance.
- moisture-curing hot melt adhesive is used for interior parts of automobiles and automobile interior materials, the cured moisture-curing hot melt adhesive turns yellow and deteriorates over time due to sunlight transmitted through the glass (ultraviolet rays). There are things to do.
- Patent Documents 1 to 3 are not intended for use in interior parts of houses and automobile interior materials, and it is difficult to say that they are sufficiently excellent in light resistance.
- the present invention has been made to solve such a problem, and the problem is to provide a moisture-curable hot melt adhesive having excellent light resistance and durability against high temperature and high humidity.
- the present inventors have surprisingly obtained a moisture-curable hot melt adhesive having excellent light resistance and durability when an acrylic polymer and an isocyanate compound are blended with a specific polyol. As a result, the present invention has been completed.
- the present invention provides, in one aspect, moisture curing including a urethane prepolymer having an isocyanate group at the terminal and an acrylic polymer, wherein the urethane prepolymer has a chemical structure derived from a polycarbonate polyol and an amorphous polyester polyol.
- a mold hot melt adhesive is provided.
- the present invention provides a moisture curable hot melt adhesive having a chemical structure in which the acrylic polymer is derived from a polymer of (meth) acrylic acid ester.
- the present invention provides, as a preferred embodiment, a moisture curable hot melt adhesive used for the production of automobile interior materials.
- the present invention provides a moisture curable hot melt adhesive in which an amorphous polyester polyol is obtained by a reaction between an aliphatic diol and an aromatic dicarboxylic acid.
- the aliphatic diol preferably contains at least one selected from 2,4-diethyl-1,5-pentanediol and 2-ethyl 2-butyl-1,3-propanediol.
- the aromatic dicarboxylic acid preferably contains phthalic acid.
- the moisture-curable hot melt adhesive of the present invention includes a urethane prepolymer having an isocyanate group at the terminal and an acrylic polymer, and the urethane prepolymer has a chemical structure derived from a polycarbonate polyol and an amorphous polyester polyol. Therefore, it is excellent in light resistance, hardly deteriorates even at high temperature and high humidity, and has high durability.
- the moisture curable hot melt adhesive of the present invention is excellent in the balance between light resistance and durability because the amorphous polyester polyol is obtained by the reaction of an aliphatic diol and an aromatic dicarboxylic acid.
- the aliphatic diol contains at least one selected from 2,4-diethyl-1,5-pentanediol and 2-ethyl-2-butyl-1,3-propanediol, so that an alkyl group having 2 or more carbon atoms is ester-bonded And the light resistance of the moisture curable hot melt adhesive is improved.
- the ester bond is stabilized, and a moisture-curable hot-melt adhesive having an excellent balance of light resistance and durability can be obtained. Since the automobile interior material of the present invention is obtained by applying the moisture curable reactive hot melt adhesive, the moisture curable hot melt adhesive deteriorates even in sunlight (ultraviolet rays) or in a severe hot and humid state in summer. It will not peel off in the car for a long time.
- the moisture-curing hot melt adhesive comprises “a urethane prepolymer having an isocyanate group at its end”.
- the “urethane prepolymer having an isocyanate group at the end” according to the present invention is a compound usually understood as “urethane prepolymer”, having an isocyanate group at the end, and a polycarbonate polyol and an amorphous polyester. It has a chemical structure derived from polyols.
- the chemical structure derived from the polycarbonate polyol and the amorphous polyester polyol may be incorporated in the urethane prepolymer in any form as long as the target moisture-curable hot melt adhesive can be obtained. That is, any position of the chemical structure derived from the polycarbonate polyol and the amorphous polyester polyol may be substituted with any substituent, but may not be substituted.
- the polycarbonate polyol is not particularly limited as long as the moisture-curable hot melt adhesive intended by the present invention can be obtained.
- the polyol has 2 to 18 carbon atoms and 3 to 3 carbon atoms. Obtained by ring-opening polymerization of a polycarbonate polyol obtained by reacting 18 carbonate compounds or phosgene, and a cyclic carbonate compound having 3 to 18 carbon atoms with a polyol such as a low molecular polyol, polyether polyol, polyester polyol, and polycarbonate polyol.
- a polyol such as a low molecular polyol, polyether polyol, polyester polyol, and polycarbonate polyol. Examples of the polycarbonate polyol are as follows.
- polyol having 2 to 18 carbon atoms examples include ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 3-methyl-1,5-pentanediol, and 1,6-hexane.
- Examples of the carbonate compound having 3 to 18 carbon atoms include dimethyl carbonate, diethyl carbonate, ethylene carbonate, and diphenyl carbonate.
- a polycarbonate polyol containing a polyol having 4 to 12 carbon atoms as a constituent component is preferable. More preferably, the polycarbonate polyol is an aliphatic polycarbonate polyol.
- the number average molecular weight (Mn) of the polyol is preferably from 400 to 10,000, particularly preferably from 500 to 8,000. These polycarbonate polyols may be used alone or in combination.
- the amorphous polyester polyol is not particularly limited as long as the moisture-curable hot melt adhesive targeted by the present invention can be obtained, but generally refers to an amorphous polyester polyol. Specifically, it refers to a polyester polyol having no melting point.
- Amorphous polyester polyol can be obtained by reaction of carboxylic acid and aliphatic polyol. Carboxylic acids are roughly classified into aromatic carboxylic acids and aliphatic carboxylic acids.
- Examples of the aromatic carboxylic acid include phthalic acid, trimellitic acid, and naphthalenedicarboxylic acid.
- Examples of the aliphatic carboxylic acid include succinic acid, adipic acid, pimelic acid, suberic acid, and azelaic acid.
- Examples of the aliphatic polyol include ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,7- Heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,12-dodecanediol, 3-methyl-1,5-pentanediol, 2-methyl-1,8- Octanediol, 2,2-diethyl-1,3-propanediol, 2,2-diethyl-1,3-pentanediol, 2-ethyl-2-butyl-1,3-propanediol, 2,4-diethyl- 1,5-pentanediol, 1,4-cyclohexanedimethanol, diethylene glycol, tri
- the amorphous polyester polyol is preferably obtained by a reaction between an aliphatic diol and an aromatic dicarboxylic acid.
- Aliphatic diols include 2-methyl-1,8-octanediol, 2,2-diethyl-1,3-propanediol, 2,2-diethyl-1,3-pentanediol, 2-ethyl-2-butyl-1 2,3-propanediol and 2,4-diethyl-1,5-pentanediol are preferred, and in particular, 2-ethyl-2-butyl-1,3-propanediol and 2,4-diethyl-1,5-pentanediol are preferred. desirable.
- the aromatic dicarboxylic acid is preferably phthalic acid.
- phthalic acid is a concept that includes all of ortho, meta, and para forms of benzenedicarboxylic acid, and also includes isophthalic acid (meta form) and terephthalic acid (para form).
- the aromatic dicarboxylic acid may contain an acid anhydride. Examples of the acid anhydride include phthalic anhydride. These aromatic dicarboxylic acids and aliphatic diols may be used alone or in combination.
- the number average molecular weight (Mn) of the amorphous polyester polyol is preferably 400 to 10,000, and more preferably 500 to 8,000.
- the amorphous polyester polyol of the present invention may contain lactone such as caprolactone at 20% by weight or less as a constituent component, and 10% by weight or less of oxyacid having 2 to 12 carbon atoms such as hydroxypivalic acid. It may be included.
- the non-crystalline polyester polyol may be used alone or in combination of a plurality of types.
- the urethane prepolymer regarding this invention has the chemical structure derived from a polycarbonate polyol and an amorphous polyester polyol, the chemistry derived from other polyols (for example, crystalline polyester polyol, polyether polyol, etc.). It may contain a structure.
- the crystalline polyester polyol refers to what is generally regarded as a crystalline polyester polyol, and specifically refers to a polyester polyol having a melting point.
- the melting point refers to a value measured by DSC (differential scanning calorimeter). The differential scanning calorimeter measures the difference in calorie between the measurement sample and the reference material, and the melting point of the measurement material is obtained. Specifically, the melting point is the peak top of the endothermic peak observed when the temperature is raised from ⁇ 50 ° C. to 150 ° C. at 10 ° C./min.
- the polyether polyol includes, for example, polyoxytetramethylene glycol (PTMG), polyoxypropylene glycol (PPG), polyoxyethylene glycol (PEG) and the like.
- PTMG polyoxytetramethylene glycol
- PPG polyoxypropylene glycol
- PEG polyoxyethylene glycol
- polyether polyol polyoxypropylene glycol is particularly preferable.
- the isocyanate compound is not particularly limited as long as the target urethane prepolymer can be obtained, and any isocyanate compound can be used as long as it is used for ordinary polyurethane production.
- the isocyanate compound a compound having an average of 1 to 3 isocyanate groups per molecule is preferable, and a bifunctional isocyanate compound, so-called diisocyanate compound is particularly preferable.
- An isocyanate compound can be used individually or in combination of 2 or more types.
- isocyanate compound examples include ethylene diisocyanate, ethylidene diisocyanate, propylene diisocyanate, butylene diisocyanate, hexamethylene diisocyanate, toluene diisocyanate, cyclopentylene-1,3-diisocyanate, cyclohexylene-1,4-diisocyanate, Cyclohexylene-1,2-diisocyanate, 4,4'-diphenylmethane diisocyanate, 2,2'-diphenylpropane-4,4'-diisocyanate, p-phenylene diisocyanate, m-phenylene diisocyanate, xylylene diisocyanate, 1,4- Naphthylene diisocyanate, 1,5-naphthylene diisocyanate, diphenyl-4,4'-diisocyanate, azobenzene 4,4'-di
- urethane prepolymer When producing the “urethane prepolymer” according to the present invention, monools and monoisocyanates can be used, and trifunctional polyols and trifunctional isocyanates can be used as long as the desired urethane prepolymer can be obtained. However, it is preferable to produce using a bifunctional polyol (diol) and a difunctional isocyanate (diisocyanate).
- the “urethane prepolymer” is produced by reacting a difunctional polyol and a difunctional isocyanate, and the heat stability of the resulting moisture-curable hot melt adhesive and the control of the production method (and its production process) are controlled. From the point, it is more preferable. In addition, it is preferable to use 2 mol of difunctional isocyanate with respect to 1 mol of bifunctional polyol, since the intended urethane prepolymer can be produced relatively easily.
- the moisture-curing hot melt adhesive according to the present invention is produced by mixing the above-mentioned “urethane prepolymer” and (acrylic polymer).
- a moisture-curing hot melt adhesive may be produced by mixing a pre-manufactured “urethane prepolymer” and an acrylic polymer, or a polyol that is a precursor of the urethane prepolymer.
- a moisture curable hot-melt adhesive may be produced by mixing polyol and isocyanate compound with an acrylic polymer and then reacting polyol and isocyanate compound.
- acrylic acid and methacrylic acid are collectively referred to as “(meth) acrylic acid”, and “acrylic ester and methacrylic ester” are collectively referred to as “(meth) acrylic ester” or “(meth ) Acrylate ”and acrylic acid derivatives and methacrylic acid derivatives are collectively referred to as (meth) acrylic acid derivatives.
- acrylamide and methacrylamide are collectively referred to as “(meth) acrylic acid amide”.
- a vinyl ester having a structure in which a vinyl group and oxygen are bonded, such as vinyl acetate, is not included in the (meth) acrylic ester and therefore does not correspond to the acrylic polymer of the present invention.
- (Meth) acrylic acid derivatives include N-hexyl acrylate amide, N-octyl acrylate amide, N, N-dimethyl acrylate amide, N-butyl acrylate amide, N-propyl acrylate amide, acrylonitrile and An example is methacrylonitrile.
- the acrylic polymer preferably has a chemical structure derived from a polymer of (meth) acrylic acid ester.
- (meth) acrylic acid ester methyl (meth) At least one selected from acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, and 2-hydroxyethyl (meth) acrylate is desirable.
- the production method of the acrylic polymer can be used without any particular limitation as long as it is a production method capable of obtaining the moisture-curable hot melt adhesive targeted by the present invention. Usually, it can manufacture using solution polymerization, block polymerization, suspension polymerization, etc.
- the weight average molecular weight (Mw) of the acrylic polymer is preferably 2000 to 40000, particularly preferably 2500 to 35000, and most preferably 2500 to 30000.
- the weight average molecular weight means a value measured and converted by gel permeation chromatography (GPC) regardless of whether it is Mw of a polyol or Mw of another component. More specifically, Mw refers to a value measured and converted using the following GPC apparatus and measurement method.
- GPC apparatus 600E manufactured by Waters was used, and RI (Waters 410) was used as a detector.
- RI Waters 410 was used as a detector.
- Two LF-804s manufactured by Shodex were used as GPC columns.
- the sample was dissolved in tetrahydrofuran, the flow rate was 1.0 ml / min, the column temperature was 40 ° C., and the measured molecular weight was converted using a calibration curve using monodisperse molecular weight polystyrene as a standard substance ( Or correction) and Mw was obtained.
- the blending amount of the polycarbonate polyol is preferably 40 to 80 parts by weight, particularly 50 to 70 parts by weight with respect to 100 parts by weight of the total weight of the polycarbonate polyol, the amorphous polyester polyol and the acrylic polymer. It is desirable to be.
- the blending amount of the polycarbonate polyol is in the above range, a moisture curable hot melt adhesive having an excellent balance between light resistance and durability against high temperature and high humidity can be obtained.
- the moisture curable hot melt adhesive of the present invention preferably has a melt viscosity at 120 ° C. of 3,000 mPa ⁇ s to 10,000 mPa ⁇ s, and preferably 4,000 mPa ⁇ s to 8,0000 mPa ⁇ s. More preferably, it is particularly preferably 5,000 mPa ⁇ s to 9,000 mPa ⁇ s.
- the moisture curable hot melt adhesive of the present invention can be easily applied to automobile interior materials.
- the melt viscosity at 120 ° C. is a value obtained by melting a moisture-curable hot melt adhesive at 120 ° C. and measuring the viscosity at 120 ° C. using a Brookfield viscometer (manufactured by Brookfield). Say. When measuring the viscosity, a number 27 rotor was used.
- the moisture curable hot melt adhesive according to the present invention does not adversely affect the reaction between the polyol and the isocyanate compound forming the urethane prepolymer, and the moisture curable hot melt adhesive targeted by the present invention can be obtained.
- the timing of adding the additive to the moisture curable hot melt adhesive is not particularly limited as long as the moisture curable hot melt adhesive targeted by the present invention can be obtained.
- the additive may be added together with the polyol and the isocyanate compound, or first, the polyol and the isocyanate compound are reacted to synthesize the urethane prepolymer, and then It may be added.
- the “additive” is usually used for a moisture-curable hot melt adhesive, and is not particularly limited as long as the moisture-curable hot melt adhesive targeted by the present invention can be obtained. Absent. Examples of such additives include plasticizers, antioxidants, pigments, ultraviolet absorbers, flame retardants, catalysts, and waxes.
- plasticizer examples include dioctyl phthalate, dibutyl phthalate, dioctyl adipate, mineral spirit, and the like.
- antioxidant examples include a phenol-based antioxidant, a phosphite-based antioxidant, a thioether-based antioxidant, and an amine-based antioxidant.
- Examples of the “pigment” include titanium oxide and carbon black.
- Examples of the “ultraviolet absorber” include benzotriazole, hindered amine, benzoate, and hydroxyphenyltriazine.
- Examples of the “flame retardant” include halogen flame retardants, phosphorus flame retardants, antimony flame retardants, metal hydroxide flame retardants, and the like.
- Catalysts include metal catalysts such as tin catalysts (trimethyltin laurate, trimethyltin hydroxide, dibutyltin dilaurate, dibutyltin maleate, etc.), lead catalysts (lead oleate, lead naphthenate, and octene). Lead acid), other metal catalysts (metal naphthenate such as cobalt naphthenate), and amine catalysts such as triethylenediamine, tetramethylethylenediamine, tetramethylhexylenediamine, diazabicycloalkenes, and dialkyl Examples include aminoalkylamines.
- waxes such as paraffin wax and microcrystalline wax.
- the “adherend” of the automobile interior material is not particularly limited, but a fibrous material is preferable.
- the fibrous material is a synthetic fiber or natural fiber knitted with a spinning machine into a sheet shape.
- the “base material” of the automobile interior material is not particularly limited, but a thermoplastic resin is preferable.
- a thermoplastic resin for example, Heat-resistant polystyrene resins such as styrene-acrylic acid copolymer, styrene-maleic anhydride copolymer, and styrene-itaconic acid copolymer; A resin mixture of a PPE resin and a PS resin, and a modified PPE resin such as a styrene / phenylene ether copolymer such as a styrene graft polymer to the PPE; Polycarbonate resins; and polyester resins exemplified by polybutylene terephthalate and polyethylene terephthalate.
- thermoplastic resin used as the base material is preferably polyethylene terephthalate, and the polyethylene terephthalate may be non-foamed or foamed.
- the automobile interior material of the present invention it is not necessary to use a special apparatus, and it can be manufactured using a generally known manufacturing apparatus including a transfer machine, a coater, a press machine, a heater, and a cutting machine. it can.
- the moisture curable hot melt adhesive of the present invention is applied to a substrate or an adherend with a coater while flowing the substrate and the adherend with a conveyor.
- the temperature at the time of application is controlled to a predetermined temperature with a heater.
- the adherend is lightly pressed against the substrate with a press, and the adherend and the substrate are bonded together via a moisture-curable hot melt adhesive.
- the adhered adherend and the substrate are allowed to cool, and are allowed to flow as they are with a transport machine to solidify the moisture-curable hot melt adhesive.
- the base material with the adherend is cut into an appropriate size with a cutting machine.
- a moisture curable hot-melt adhesive comprising a urethane prepolymer having an isocyanate group at its terminal and an acrylic polymer, wherein the urethane prepolymer has a chemical structure derived from a polycarbonate polyol and an amorphous polyester polyol.
- An automotive interior material obtained by applying the moisture-curable reactive hot melt adhesive according to any one of 1 to 6 above.
- Amorphous polyester polyol A (PES-A (product name) manufactured by Henkel Japan Co., Ltd., hydroxyl value 57.5 (mgKOH / g), number average molecular weight (Mn) 2000, 2-butyl-2-ethyl-1,3- Polyester polyol produced from propanediol and phthalic acid)
- Amorphous polyester polyol B (HS 2N-226P (product name) manufactured by Toyokuni Oil Co., Ltd., hydroxyl value 56 (mgKOH / g), number average molecular weight (Mn) 2000, 2,4-diethyl-1,5-pentanediol and Polyester polyol produced from phthalic acid) Crystalline polyester polyol (HS 2H-351A (product name) manufactured by Toyokuni Oil Co., Ltd., hydroxyl value 56 (mgKOH / g), number average molecular weight (Mn) 3500, polyester polyol manufactured from 1,6
- Polypropylene glycol (Daiichi Kogyo Seiyaku Co., Ltd. Highflex D2000 (product name), hydroxyl value 56 (mgKOH / g), number average molecular weight (Mn) 2000)
- Ethylene vinyl acetate resin (Ultrasen 726-2 (product name) manufactured by Tosoh Corporation, vinyl acetate content 31%, melt index 700 (g / 10 min 190 ° C.))
- ⁇ Isocyanate compound > Xylylene diisocyanate (Takenate 500 (product name) manufactured by Mitsui Chemicals, Inc.) ⁇ Additives> UV absorber (manufactured by BASF Tinuvin 479 (product name), hydroxytriazine UV absorber) Antioxidant 1 (Adeka Stub AO-50 (product name), phenolic antioxidant manufactured by Adeka) Antioxidant 2 (Eversorb 93 (product name) manufactured by Eiko Chemical Co., Ltd., amine antioxidant)
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- Polyurethanes Or Polyureas (AREA)
- Vehicle Interior And Exterior Ornaments, Soundproofing, And Insulation (AREA)
Abstract
Description
本発明は、好ましい態様として、自動車内装材の製造に使用される湿気硬化型ホットメルト接着剤を提供する。
脂肪族ジオールは、2,4-ジエチル-1,5ペンタンジオールおよび2-エチル2-ブチル-1,3-プロパンジオールから選ばれる少なくとも1種を含むことが好ましい。
芳香族ジカルボン酸は、フタル酸を含むことが好ましい。
従って、本発明の湿気硬化型ホットメルト接着剤は、自動車内装材の製造に好適に使用される。
脂肪族ジオールは、2,4-ジエチル-1,5ペンタンジオールおよび2-エチル2-ブチル-1,3-プロパンジオールから選ばれる少なくとも1種を含むので、炭素数2以上のアルキル基がエステル結合を保護し、湿気硬化型ホットメルト接着剤の耐光性が向上する。
本発明の自動車内装材は、上記湿気硬化型反応性ホットメルト接着剤を塗布して得られるので、太陽光(紫外線)や夏場の過酷な高温多湿状態でも湿気硬化型ホットメルト接着剤が劣化せず、長期間、自動車内で剥がれたりすることがない。
本発明に係る「イソシアネート基を末端に有するウレタンプレポリマー」とは、通常「ウレタンプレポリマー」と理解される化合物であって、イソシアネート基を末端に有し、かつ、ポリカーボネートポリオールおよび非晶性ポリエステルポリオールに由来する化学構造を有する。
炭素数3~18の環状カーボネート化合物を、低分子ポリオール、ポリエーテルポリオール、ポリエステルポリオール及びポリカーボネートポリオール等のポリオールで開環重合させて得られるポリカーボネートポリオールを例示できる。
ポリカーボネートポリオールは、脂肪族ポリカーボネートポリオールであることがさらに好ましい。ポリオールの数平均分子量(Mn)は400~10000が好ましく、500~8000が特に好ましい。
これらのポリカーボネートポリオールは単独で使用しても良いし、複数で使用しても良い。
非晶性ポリエステルポリオールは、カルボン酸と脂肪族ポリオールとの反応で得ることができる。カルボン酸は、芳香族カルボン酸及び脂肪族カルボン酸に大別される。
脂肪族カルボン酸としては、例えば、コハク酸、アジピン酸、ピメリン酸、スベリン酸、及びアゼライン酸が挙げられる。
脂肪族ジオールは、2-メチル-1,8-オクタンジオール、2,2-ジエチル-1,3-プロパンジオール、2,2-ジエチル-1,3ペンタンジオール、2-エチル-2-ブチル-1,3-プロパンジオール、2,4-ジエチル-1,5ペンタンジオールが好ましく、特に、2-エチル-2-ブチル-1,3-プロパンジオール、及び2,4-ジエチル-1,5ペンタンジオールが望ましい。
さらに、芳香族ジカルボン酸は、酸無水物を含んでいても差し支えない。酸無水物としては、フタル酸無水物が挙げられる。
これらの芳香族ジカルボン酸、脂肪族ジオールは、単独で使用しても良いし、混合していても良い。
本発明の非結晶性ポリエステルポリオールは、その構成成分としてカプロラクトン等のラクトンを20重量%以下で含有していても良いし、ヒドロキシピバリン酸などの炭素数2~12のオキシ酸を10重量%以下で含んでいても良い。
さらに、非結晶性ポリエステルポリオールは、単独で使用しても良いし、複数種類を組み合わせて使用しても良い。
融点は、DSC(示差走査熱量計)で測定された値をいう。示差走査熱量計によって、測定試料と基準物質との間の熱量の差が計測され、測定資料の融点が得られる。具体的には、-50℃から10℃/分で150℃まで昇温して観察される吸熱ピークのピークトップを融点とする。
非晶性ポリエステルポリオールの融点はDSCで測定すると、明確に観察されないことから、結晶性ポリエステルポリオールと区別することは可能である。
尚、一般的に、結晶性ポリエステルポリオールは固体状態で白色不透明であるのに対し、非晶性ポリエステルポリオールは透明である。
本発明に係る湿気硬化型ホットメルト接着剤は、上述の「ウレタンプレポリマー」と(アクリル系重合体とを混合することで製造される。
尚、ビニル基と酸素が結合した構造を有するビニルエステル、例えば酢酸ビニル等は、(メタ)アクリルエステルに含まれないので、本発明のアクリル系重合体に該当しない。
本明細書においては、120℃での溶融粘度は、湿気硬化型ホットメルト接着剤を120℃で溶融し、ブルックフィールド粘度計(ブルックフィールド社製)を用いて、120℃で粘度を測定した値をいう。粘度を測定する際、番号27のローターを使用した。
「酸化防止剤」として、例えば、フェノール系酸化防止剤、ホスファイト系酸化防止剤、チオエーテル系酸化防止剤、及びアミン系酸化防止剤等を例示できる。
「紫外線吸収剤」として、例えば、ベンゾトリアゾール、ヒンダードアミン、ベンゾエート、及びヒドロキシフェニルトリアジン等を例示できる。
「難燃剤」として、例えば、ハロゲン系難燃剤、リン系難燃剤、アンチモン系難燃剤、及び金属水酸化物系難燃剤等を例示できる。
スチレン-アクリル酸共重合体、スチレン-無水マレイン酸共重合体、及びスチレン-イタコン酸共重合体等の耐熱性ポリスチレン系樹脂;
PPE系樹脂とPS系樹脂との樹脂混合物、及びPPEへのスチレングラフト重合体等のスチレン・フェニレンエーテル共重合体等の変性PPE系樹脂;、
ポリカーボネート樹脂;及び
ポリブチレンテレフタレート及びポリエチレンテレフタレートで例示されるポリエステル系樹脂などが挙げられる。
基材となる熱可塑性樹脂はポリエチレンテレフタレートが好ましく、ポリエチレンテレフタレートは非発泡体でも、発泡体でも差し支えない。
1.イソシアネート基を末端に有するウレタンプレポリマーと、アクリル系重合体を含み、ウレタンプレポリマーは、ポリカーボネートポリオールおよび非晶性ポリエステルポリオールに由来する化学構造を有する湿気硬化型ホットメルト接着剤。
2.アクリル系重合体は、(メタ)アクリル酸エステルの重合体に由来する化学構造を有する上記1に記載の湿気硬化型ホットメルト接着剤。
3.自動車内装材の製造に使用される上記1又は2に記載の湿気硬化型ホットメルト接着剤。
4.非晶性ポリエステルポリオールは、脂肪族ジオールと芳香族ジカルボン酸との反応で得られる、上記1~3のいずれかに記載の湿気硬化型ホットメルト接着剤。
5.脂肪族ジオールは、2,4-ジエチル-1,5ペンタンジオールおよび2-エチル2-ブチル-1,3-プロパンジオールから選ばれる少なくとも1種を含む上記4に記載の湿気硬化型ホットメルト接着剤。
6.芳香族ジカルボン酸は、フタル酸を含む上記4又は5に記載の湿気硬化型反応性ホットメルト接着剤。
7.上記1~6のいずれかに記載の湿気硬化型反応性ホットメルト接着剤を塗布して得られる自動車内装材。
<ポリカーボネートポリオール>
ポリカーボネートジオールA(旭化成ケミカルズ社製 デュラネートT4692(製品名)、水酸基価56(mgKOH/g)、数平均分子量(Mn)2000、 1,4-ブタンジオールと1,6-ヘキサンジオールから製造されるポリカーボネートポリオール)
ポリカーボネートジオールB(旭化成ケミカルズ社製 デュラネートT5652(製品名)、水酸基価56(mgKOH/g)、重量平均分子量(Mw)2000、 1,5-ペンタンジオールと1,6-ヘキサンジオールから製造されるポリカーボネートジオール)
非晶性ポリエステルポリオールA(ヘンケルジャパン社製 PES-A(製品名)、水酸基価57.5(mgKOH/g)、数平均分子量(Mn)2000、2-ブチル-2-エチル-1,3-プロパンジオールとフタル酸から製造されるポリエステルポリオール)
非晶性ポリエステルポリオールB(豊国製油社製 HS 2N-226P(製品名)、水酸基価56(mgKOH/g)、数平均分子量(Mn)2000、 2,4-ジエチル-1,5-ペンタンジオールとフタル酸から製造されるポリエステルポリオール)
結晶性ポリエステルポリオール(豊国製油社製 HS 2H-351A(製品名)、水酸基価56(mgKOH/g)、数平均分子量(Mn)3500、 1,6-ヘキサンジオールとアジピン酸から製造されるポリエステルポリオール)
ポリプロピレングリコール(第一工業製薬社製 ハイフレックスD2000(製品名)、水酸基価56(mgKOH/g)、数平均分子量(Mn)2000)
メチルメタクリレート(MMA)、2-ヒドロキシエチルメタクリレート(2HEMA)およびブチルアクリレート(BA)の共重合体(イネオスアクリル社製 イソクリルH-270(製品名)、水酸基価13(mgKOH/g)、重量平均分子量(Mw)27000)
ブチルアクリレート(BA)の単独重合体(東亞合成社製 アルフォンUP1000(製品名)、重量平均分子量(Mw)3000)
エチレン酢酸ビニル樹脂(EVA樹脂)(東ソー社製 ウルトラセン726-2(製品名)、酢酸ビニル含量31%、メルトインデックス700(g/10分 190℃))
キシリレンジイソシアネート(三井化学社製 タケネート500(製品名))
<添加剤>
紫外線吸収剤(BASF社製 チヌビン479(製品名)、ヒドロキシトリアジン系紫外線吸収剤)
酸化防止剤1(アデカ社製 アデカスタブAO-50(製品名)、フェノール系酸化防止剤)
酸化防止剤2(永光化学社製 エバーソーブ93(製品名)、アミン系酸化防止剤)
2-ブチル-2-エチル-1,3-プロパンジオール345.6g、及びフタル酸296gを反応容器に入れ、触媒として酢酸亜鉛0.2gを仕込み、2時間かけて220℃まで昇温し、常圧で1時間攪拌し、反応させた。水の溜出を確認後、減圧下で5時間反応させ、所定量の水が除去されたことを確認し、ポリエステルポリオール(PES-A)を得た。 水酸基価をJIS K1557-1に従って、測定したところ、57.5mgKOH/gであった。
実施例1~10および比較例1~7
原料を表1及び表2に示す組成で混合し、湿気硬化型ホットメルト接着剤を製造した。
具体的には、イソシアネート化合物以外の全ての原料を反応容器に入れ、120℃に昇温し、減圧下で1時間撹拌した。水分を取り除いた後、同温度でイソシアネート化合物(キシリレンジイソシアネート)を添加し、減圧下で2時間撹拌し、湿気硬化型ホットメルト接着剤を得た。
更に塗工性能を評価するために粘度を測定した。
以下に試験方法及び評価基準を記載する。
試験片の作製:接着剤を隠蔽性試験紙(JIS)へ200μmの厚みで均一に塗布し、室温で3日間養生して硬化させた。
硬化させた接着剤/隠蔽性試験紙の白色部分にフェードメーター(スガ試験機社製)を用いて、紫外線を83℃で200時間照射した。
照射前後で色差(Δb値)を色差計(日本電色工業製 グロスメーターVG700)で測定した。
色差については、以下のように評価した。
◎: Δb値 4未満
○: Δb値 4以上で、6未満
△: Δb値 6以上で、10未満
×: Δb値 10以上
試験片の作製
ポリエチレンテレフタレート(PET)フォームへ接着剤を15g/m2の塗布量スプレー塗工し、PETクロスを貼り合わせ60℃、0.2MPa、30秒間プレスを行い貼り合わせ試験片を作製した。貼り合わせた試験片を色差の測定同様に、フェードメーター(スガ試験機社製)を用いて、紫外線を83℃で200時間照射した。
照射前後でピール強度の測定を行い、強度維持率を算出した。ピール強度は引っ張り試験機(JTトーシ社製 SC-50NM-S0)を用いて、引っ張り速度100mm/分、T型剥離試験で測定した。
強度維持率は以下のように評価した。
強度維持率(%)=照射後のピール強度/照射前のピール強度×100
○: 強度維持率80%以上
×: 強度維持率80%未満
試験片の作製:接着剤をアルミシートへ200μmの厚みで均一に塗布し、室温で3日間養生して硬化させた。硬化させた接着剤/アルミシートをオートクレーブ(ヤマト科学社製 オートクレーブSP300)に入れ、ハイプレッシャークッカー試験を実施した。
ハイプレッシャークッカー試験では、試験片に対し、温度120℃、内圧1.1MPa(大気圧1.0MPaおよび蒸気圧0.1MPaの総圧)、24時間の負荷をかけた。
その後、試験片を取り出し、爪を立て表面の状態を確認した。
○:試験前後で表面の状態に差が無い。
×:試験後、明らかに表面が軟化し、簡単に爪が入る。
粘度測定は、粘度計(ブルックフィールド社製)を用い、番号27のローターを使用した。溶融した湿気硬化型ホットメルト接着剤を規定量(10.5g)粘度管に流し、ローターを粘度計へ差し込み、120℃で30分間放置した後、120℃溶融粘度を測定した。
本発明に係る湿気硬化型ホットメルト接着剤は、耐光性および耐久性に優れているので自動車内装材用途として好適である。
本発明に係る自動車内装材は、高温多湿等の過酷な条件が長期間続いても、基材樹脂と被着体とが剥がれることがない。
[関連出願]
尚、本出願は、2011年12月5日に日本国でされた出願番号2011-265982を基礎出願とするパリ条約第4条に基づく優先権を主張する。この基礎出願の内容は、参照することによって、本明細書に組み込まれる。
Claims (4)
- イソシアネート基を末端に有するウレタンプレポリマーと、アクリル系重合体を含み、
ウレタンプレポリマーは、ポリカーボネートポリオールおよび非晶性ポリエステルポリオールに由来する化学構造を有する湿気硬化型ホットメルト接着剤。 - アクリル系重合体は、(メタ)アクリル酸エステルの重合体に由来する化学構造を有する請求項1に記載の湿気硬化型ホットメルト接着剤。
- 自動車内装材の製造に使用される請求項1又は2に記載の湿気硬化型ホットメルト接着剤。
- 請求項1~3のいずれかに記載の湿気硬化型反応性ホットメルト接着剤を塗布して得られる自動車内装材。
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KR20147015106A KR20140101754A (ko) | 2011-12-05 | 2012-12-04 | 습기 경화형 핫 멜트 접착제 |
EP12854658.7A EP2789667B1 (en) | 2011-12-05 | 2012-12-04 | Moisture-curable hot melt adhesive |
ES12854658.7T ES2623033T3 (es) | 2011-12-05 | 2012-12-04 | Adhesivo de fusión en caliente curable por humedad |
CN201280059497.3A CN103998556B (zh) | 2011-12-05 | 2012-12-04 | 可湿气固化的热熔粘合剂 |
RU2014127490A RU2014127490A (ru) | 2011-12-05 | 2012-12-04 | Влагоотверждаемый термоплавкий клей |
BR112014011798A BR112014011798A2 (pt) | 2011-12-05 | 2012-12-04 | adesivo de fusão a quente curável com umidade |
US14/293,006 US20140272425A1 (en) | 2011-12-05 | 2014-06-02 | Moisture-curable hot melt adhesive |
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JP2011265982A JP2013116993A (ja) | 2011-12-05 | 2011-12-05 | 湿気硬化型ホットメルト接着剤 |
JP2011-265982 | 2011-12-05 |
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US14/293,006 Continuation US20140272425A1 (en) | 2011-12-05 | 2014-06-02 | Moisture-curable hot melt adhesive |
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WO2013084891A1 true WO2013084891A1 (ja) | 2013-06-13 |
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US (1) | US20140272425A1 (ja) |
EP (1) | EP2789667B1 (ja) |
JP (1) | JP2013116993A (ja) |
KR (1) | KR20140101754A (ja) |
CN (1) | CN103998556B (ja) |
BR (1) | BR112014011798A2 (ja) |
CL (1) | CL2014001458A1 (ja) |
ES (1) | ES2623033T3 (ja) |
RU (1) | RU2014127490A (ja) |
WO (1) | WO2013084891A1 (ja) |
Cited By (1)
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WO2016002335A1 (ja) * | 2014-07-02 | 2016-01-07 | 横浜ゴム株式会社 | 反応性ホットメルト接着剤組成物 |
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WO2015016029A1 (ja) * | 2013-07-31 | 2015-02-05 | Dic株式会社 | 湿気硬化型ホットメルトウレタン組成物及び接着剤 |
CN107109177A (zh) * | 2014-09-26 | 2017-08-29 | 汉高股份有限及两合公司 | 反应性聚氨酯热熔粘合剂及其用途 |
JP6447083B2 (ja) * | 2014-12-16 | 2019-01-09 | Dic株式会社 | 湿気硬化型ポリウレタンホットメルト樹脂組成物、接着剤及び積層体 |
WO2017156269A1 (en) * | 2016-03-10 | 2017-09-14 | Momentive Performance Materials Inc. | Moisture-curable silylated resin derived from polycarbonate diol and coating, sealant and adhesive compositions containing same |
JP6960656B2 (ja) * | 2017-04-11 | 2021-11-05 | 積水フーラー株式会社 | 湿気硬化型ホットメルト接着剤 |
JP2019203083A (ja) * | 2018-05-24 | 2019-11-28 | Dic株式会社 | 湿気硬化型ウレタンホットメルト樹脂組成物、及び、積層体 |
WO2020003778A1 (ja) * | 2018-06-28 | 2020-01-02 | Dic株式会社 | 湿気硬化型ポリウレタンホットメルト樹脂組成物 |
WO2024194971A1 (ja) * | 2023-03-20 | 2024-09-26 | Kfケミカル株式会社 | 一液型湿気硬化性ウレタン樹脂組成物およびそれを用いた塗料 |
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- 2012-12-04 CN CN201280059497.3A patent/CN103998556B/zh active Active
- 2012-12-04 BR BR112014011798A patent/BR112014011798A2/pt not_active IP Right Cessation
- 2012-12-04 KR KR20147015106A patent/KR20140101754A/ko not_active Application Discontinuation
- 2012-12-04 ES ES12854658.7T patent/ES2623033T3/es active Active
- 2012-12-04 RU RU2014127490A patent/RU2014127490A/ru not_active Application Discontinuation
- 2012-12-04 EP EP12854658.7A patent/EP2789667B1/en active Active
- 2012-12-04 WO PCT/JP2012/081389 patent/WO2013084891A1/ja active Application Filing
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- 2014-06-02 US US14/293,006 patent/US20140272425A1/en not_active Abandoned
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WO2016002335A1 (ja) * | 2014-07-02 | 2016-01-07 | 横浜ゴム株式会社 | 反応性ホットメルト接着剤組成物 |
US10174233B2 (en) | 2014-07-02 | 2019-01-08 | The Yokohama Rubber Co., Ltd. | Reactive hot-melt adhesive composition |
Also Published As
Publication number | Publication date |
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RU2014127490A (ru) | 2016-01-27 |
JP2013116993A (ja) | 2013-06-13 |
EP2789667A4 (en) | 2015-07-22 |
EP2789667A1 (en) | 2014-10-15 |
US20140272425A1 (en) | 2014-09-18 |
CN103998556B (zh) | 2016-07-13 |
CN103998556A (zh) | 2014-08-20 |
BR112014011798A2 (pt) | 2017-05-09 |
CL2014001458A1 (es) | 2014-10-24 |
EP2789667B1 (en) | 2017-02-08 |
ES2623033T3 (es) | 2017-07-10 |
KR20140101754A (ko) | 2014-08-20 |
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