JP7413649B2 - ウレタン樹脂組成物、ウレタン樹脂組成物接着剤及び接着方法 - Google Patents
ウレタン樹脂組成物、ウレタン樹脂組成物接着剤及び接着方法 Download PDFInfo
- Publication number
- JP7413649B2 JP7413649B2 JP2019012749A JP2019012749A JP7413649B2 JP 7413649 B2 JP7413649 B2 JP 7413649B2 JP 2019012749 A JP2019012749 A JP 2019012749A JP 2019012749 A JP2019012749 A JP 2019012749A JP 7413649 B2 JP7413649 B2 JP 7413649B2
- Authority
- JP
- Japan
- Prior art keywords
- urethane resin
- resin composition
- compound
- article
- base material
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 229920002803 thermoplastic polyurethane Polymers 0.000 title claims description 53
- 239000011342 resin composition Substances 0.000 title claims description 43
- 238000000034 method Methods 0.000 title claims description 26
- 239000000853 adhesive Substances 0.000 title claims description 20
- 230000001070 adhesive effect Effects 0.000 title claims description 20
- 239000000463 material Substances 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 35
- -1 polyethylene Polymers 0.000 claims description 35
- 239000012790 adhesive layer Substances 0.000 claims description 33
- 229920005989 resin Polymers 0.000 claims description 24
- 239000011347 resin Substances 0.000 claims description 24
- 239000004743 Polypropylene Substances 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 20
- 125000003700 epoxy group Chemical group 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 229920001155 polypropylene Polymers 0.000 claims description 13
- 239000000758 substrate Substances 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000005056 polyisocyanate Substances 0.000 claims description 10
- 229920001228 polyisocyanate Polymers 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 229920005862 polyol Polymers 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 229920000098 polyolefin Polymers 0.000 claims description 8
- 150000003077 polyols Chemical class 0.000 claims description 8
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 7
- 239000004698 Polyethylene Substances 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 229920000573 polyethylene Polymers 0.000 claims description 6
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical group OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 239000012462 polypropylene substrate Substances 0.000 claims 1
- 239000002585 base Substances 0.000 description 33
- 238000000576 coating method Methods 0.000 description 18
- 238000012360 testing method Methods 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000003822 epoxy resin Substances 0.000 description 11
- 229920000647 polyepoxide Polymers 0.000 description 11
- 238000001035 drying Methods 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 8
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Substances FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000005062 Polybutadiene Substances 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 229920002857 polybutadiene Polymers 0.000 description 5
- 229920001195 polyisoprene Polymers 0.000 description 5
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 4
- 229910015900 BF3 Inorganic materials 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 229920005749 polyurethane resin Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007809 chemical reaction catalyst Substances 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 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 3
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 238000003851 corona treatment Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 239000004210 ether based solvent Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000013022 formulation composition Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 150000004714 phosphonium salts Chemical class 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- GHBFNMLVSPCDGN-UHFFFAOYSA-N rac-1-monooctanoylglycerol Chemical compound CCCCCCCC(=O)OCC(O)CO GHBFNMLVSPCDGN-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- BYPFICORERPGJY-UHFFFAOYSA-N 3,4-diisocyanatobicyclo[2.2.1]hept-2-ene Chemical compound C1CC2(N=C=O)C(N=C=O)=CC1C2 BYPFICORERPGJY-UHFFFAOYSA-N 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- SDVVCEXZGFHIER-UHFFFAOYSA-N C(CCCCCCCCCCC)(=O)OCCCCCCCC.C(CCCCCCCCCCC)(=O)OCCCCCCCC Chemical compound C(CCCCCCCCCCC)(=O)OCCCCCCCC.C(CCCCCCCCCCC)(=O)OCCCCCCCC SDVVCEXZGFHIER-UHFFFAOYSA-N 0.000 description 1
- LKUNXBRZDFMZOK-GFCCVEGCSA-N Capric acid monoglyceride Natural products CCCCCCCCCC(=O)OC[C@H](O)CO LKUNXBRZDFMZOK-GFCCVEGCSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- ARIWANIATODDMH-UHFFFAOYSA-N Lauric acid monoglyceride Natural products CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000007611 bar coating method Methods 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N beta-monoglyceryl stearate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 239000004918 carbon fiber reinforced polymer Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000011199 continuous fiber reinforced thermoplastic Substances 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 238000007607 die coating method Methods 0.000 description 1
- KIQKWYUGPPFMBV-UHFFFAOYSA-N diisocyanatomethane Chemical compound O=C=NCN=C=O KIQKWYUGPPFMBV-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000007765 extrusion coating Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000005003 food packaging material Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000007759 kiss coating Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000007763 reverse roll coating Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000005028 tinplate Substances 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
- 238000012546 transfer Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Synthetic Leather, Interior Materials Or Flexible Sheet Materials (AREA)
- Polyurethanes Or Polyureas (AREA)
- Adhesives Or Adhesive Processes (AREA)
Description
以下の方法でウレタン樹脂組成物の製造を行った。
撹拌機、温度計、加熱装置、還流管を備えた容量2Lの四口セパラブルフラスコに、水酸基末端水添ポリイソプレン(商品名 EPOL、出光興産社製、数平均分子量2,500、水酸基含量0.9mol/kg、)を158g、ジフェニルメタン―4,4’―ジイソシアネート(以下、MDIと言う。商品名:ミリオネートMT、東ソー社製、イソシアネート基含量31.3%)を20.5g、ジラウリン酸ジオクチルスズ(キシダ化学社製)を0.111g、シクロヘキサノン(ゴードー社製)を1620g、それぞれ室温下で仕込んだ後、窒素ガスを吹き込むことでフラスコ内を窒素置換した。これらを80℃条件下で均一に撹拌しながら2時間反応させた後、グリシドール(商品名 エピオール OH、日油社製)を1.10g、80℃条件下で仕込んだ後、80℃条件下で均一に撹拌しながらさらに2時間反応させることでウレタン樹脂組成物を得た。得られたウレタン樹脂組成物について、以下の方法で数平均分子量、粘度およびエポキシ当量を測定した。
ゲル浸透クロマトグラフィー(GPC)により求めた。条件は以下の通りである。装置として高速GPC装置(東ソー社製HLC-8220)、カラムとしてG3000H-XL、G2500H-XL、G2000H-XLおよびG1000H-XL(いずれも東ソー社製)を記載の順に1本ずつ直列に接続したものを用い、移動相としてテトラヒドロフランを使用し、移動相速度を1.00mL/分とした。カラム温度は40℃とし、検出器は示差屈折率計で実施し、ポリスチレン換算分子量として分子量を求めた。サンプル溶液は濃度0.5%のTHF溶液を調製して用いた。数平均分子量は7,457であった。
JIS7117-2に準拠して、B型粘度計(芝浦システム社製ビスメトロンVS-A1)を用いて測定した。粘度は3mPa/s(25℃)であった。
JIS K7236に準拠して測定した。エポキシ当量は5,268g/eq.であった。
以下の方法でPP接着層用配合液の調製、試験片の作成および塗膜物性評価を行った。結果を表1に示す。
容量100mLのガラス瓶に、製造例1で得られたウレタン樹脂組成物、エポキシ樹脂硬化促進剤(商品名 サンエイドSI-110、三新化成社製)およびエポキシ樹脂硬化剤(ジシアンジアミド、東京化成工業社製)を表1に示す質量部で仕込んだ後、ミックスローターを用いて均一となるまで攪拌することでPP接着層用配合液を得た。
まず、PP接着層用配合組成物をポリプロプレン基材(日立化成社製コウベポリシートPP)にバーコーターを用いて塗布し、室温条件下で5分間静置した後、熱風乾燥器を用いて80℃で5分間乾燥させ、乾燥膜厚10μmの接着剤層を有するポリプロピレン試験片を得た。次に、接着層組成物として本発明のウレタン樹脂組成物とは異なるポリウレタン系樹脂(東ソー社製ニッポラン-5288、商品名)をポリエチレンテレフタレートフィルム(東洋紡製東洋紡エステルフィルムE5100)にバーコーターを用いて塗布し、室温条件下で5分間静置した後、熱風乾燥器を用いて80℃で5分間乾燥させ、乾燥膜厚10μmのポリウレタン系樹脂層を有するポリエチレンテレフタレートフィルム試験片を得た。そして、得られたそれぞれの試験片を接着剤層とポリウレタン系樹脂層が接する様に張り合わせた後、185℃で10分間加熱処理することで試験片を得た。
張り合わせて得た試験片について、JISK6854-2に準拠して180度剥離試験をおこない、接着強度を評価した。試験はオートコム型試験機(ティー・エス・イー社製UTPS-Acs(S))を用いて測定した。
製造例1で得られたウレタン樹脂組成物を用いて、実施例1と同様の方法で表1に示す組成のPP接着層用配合組成物を用いて試験片の作成および接着剤物性評価を行った。結果を表1に示す。
製造例1で得られたウレタン樹脂組成物を用いて、実施例1と同様の方法で表1に示す組成のPP接着層用配合組成物を用いて試験片の作成および接着剤物性評価を行った。結果を表1に示す。
実施例1に示す試験片の作成方法において、PP接着層用配合組成物の代わりにポリウレタン系樹脂(東ソー社製ニッポラン-5288、商品名)を用いた他は、実施例1と同様に評価を行った。結果を表1に示す。
Claims (14)
- ポリエチレン基材接着用またはポリプロピレン基材接着用のウレタン樹脂組成物であって、
下記一般式(1):
で表される化合物(A)、
ポリイソシアネート化合物(B)、及び
一分子中に水酸基とエポキシ基をそれぞれ少なくとも1つ有する化合物(C)の反応生成物であって、該反応生成物の分子末端にエポキシ基を持つことを特徴とする、ウレタン樹脂組成物。(ただし、ポリイソシアネート化合物(B)がイソホロンジイソシアネートであるものを除く。) - 前記一般式(1)で表される化合物(A)が分子中の異なる炭素上に水酸基を有し、炭素数50~400のポリオールポリオレフィンであることを特徴とする、請求項1に記載のウレタン樹脂組成物。
- 一分子中に水酸基とエポキシ基をそれぞれ少なくとも1つ有する化合物(C)がグリシドールであることを特徴とする、請求項1又は2に記載のウレタン樹脂組成物。
- 数平均分子量が3,000~250,000であることを特徴とする、請求項1乃至3のいずれかに記載のウレタン樹脂組成物。
- 前記一般式(1)で表される化合物(A)、ポリイソシアネート化合物(B)、及び一分子中に水酸基とエポキシ基をそれぞれ少なくとも1つ有する化合物(C)の反応生成物における、前記一般式(1)で表される化合物(A)の含有量が30質量%~99.9質量%であることを特徴とする、請求項1乃至4のいずれかに記載のウレタン樹脂組成物。
- 前記ポリイソシアネート化合物(B)が、ジフェニルメタンジイソシアネートを含む、請求項1乃至5のいずれかに記載のウレタン樹脂組成物。
- 請求項1乃至6のいずれかに記載のウレタン樹脂組成物を含む接着剤組成物。
- 請求項7に記載の接着剤組成物から得られる接着剤層。
- 請求項8に記載の接着剤層を有する物品。
- 接着剤層と基材とを加熱して得られ、
該基材が、ポリエチレン基材またはポリプロピレン基材である請求項9に記載の物品。 - 請求項9または10に記載の物品と他の基材とから得られる物品。
- 請求項9または10に記載の物品と樹脂が塗布された基材とから得られる物品。
- 加熱処理することにより得られることを特徴とする、請求項9乃至12のいずれかに記載の物品の製造方法。
- 70℃以上で加熱処理することを特徴とする請求項13に記載の物品の製造方法。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2019012749A JP7413649B2 (ja) | 2019-01-29 | 2019-01-29 | ウレタン樹脂組成物、ウレタン樹脂組成物接着剤及び接着方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2019012749A JP7413649B2 (ja) | 2019-01-29 | 2019-01-29 | ウレタン樹脂組成物、ウレタン樹脂組成物接着剤及び接着方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2020122038A JP2020122038A (ja) | 2020-08-13 |
JP7413649B2 true JP7413649B2 (ja) | 2024-01-16 |
Family
ID=71992196
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2019012749A Active JP7413649B2 (ja) | 2019-01-29 | 2019-01-29 | ウレタン樹脂組成物、ウレタン樹脂組成物接着剤及び接着方法 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP7413649B2 (ja) |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010507709A (ja) | 2006-10-24 | 2010-03-11 | シーカ・テクノロジー・アーゲー | 誘導体化された固体エポキシ樹脂およびその使用 |
JP2015091986A (ja) | 2014-12-26 | 2015-05-14 | 太陽ホールディングス株式会社 | フェノール基含有樹脂及びその製造方法 |
JP2016104875A (ja) | 2015-12-28 | 2016-06-09 | 味の素株式会社 | 樹脂組成物 |
JP2019001001A (ja) | 2017-06-12 | 2019-01-10 | バンドー化学株式会社 | 積層体、及び、積層体の製造方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02238019A (ja) * | 1989-03-13 | 1990-09-20 | Yokohama Rubber Co Ltd:The | エポキシ樹脂組成物 |
JPH0441582A (ja) * | 1990-06-08 | 1992-02-12 | Yokohama Rubber Co Ltd:The | 水中用封止材 |
IT1252388B (it) * | 1991-11-12 | 1995-06-12 | Sviluppo Settori Impiego Srl | Polimeri e copolimeri del propilene aggraffati con vinilpolibutadiene e procedimento di preparazione |
-
2019
- 2019-01-29 JP JP2019012749A patent/JP7413649B2/ja active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010507709A (ja) | 2006-10-24 | 2010-03-11 | シーカ・テクノロジー・アーゲー | 誘導体化された固体エポキシ樹脂およびその使用 |
JP2015091986A (ja) | 2014-12-26 | 2015-05-14 | 太陽ホールディングス株式会社 | フェノール基含有樹脂及びその製造方法 |
JP2016104875A (ja) | 2015-12-28 | 2016-06-09 | 味の素株式会社 | 樹脂組成物 |
JP2019001001A (ja) | 2017-06-12 | 2019-01-10 | バンドー化学株式会社 | 積層体、及び、積層体の製造方法 |
Also Published As
Publication number | Publication date |
---|---|
JP2020122038A (ja) | 2020-08-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Subramani et al. | New development of polyurethane dispersion derived from blocked aromatic diisocyanate | |
KR100948527B1 (ko) | 폴리이소시아네이트 조성물 및 이를 포함한 코팅 조성물 | |
JP5532224B2 (ja) | ウレタンプレポリマー | |
JP2004514015A (ja) | 高分子基体のための耐紫外線性フロック加工用接着剤 | |
US3054755A (en) | Polyurethane plastics | |
JP7413648B2 (ja) | ウレタン樹脂組成物、接着剤組成物、及び物品の製造方法 | |
JP2022517851A (ja) | バイオ由来の化合物を含む弾性接着剤 | |
JP7413649B2 (ja) | ウレタン樹脂組成物、ウレタン樹脂組成物接着剤及び接着方法 | |
JP7432807B2 (ja) | ウレタン樹脂組成物及び塗装物 | |
JPWO2013031977A1 (ja) | クリヤー塗料組成物及びそれを用いた複層塗膜の形成方法 | |
KR102317626B1 (ko) | 반응성 핫멜트 수지용 박리제 | |
US20210317252A1 (en) | Polymeric material including a uretdione-containing material and a thermally activatable amine, two-part compositions, and methods | |
TW201920335A (zh) | 包括含脲二酮材料的聚合材料、兩部分組成物、及方法 | |
JP7470892B2 (ja) | 撥液性ウレタン樹脂組成物及び樹脂塗膜 | |
WO2023243513A1 (ja) | ウレタン樹脂、接着剤、物品及び物品の製造方法 | |
JP2022179350A (ja) | ウレタン樹脂組成物、接着剤組成物、及び物品の製造方法 | |
CN110982403A (zh) | 用封端聚醚胺改性聚脲涂层的制备方法 | |
JP6808910B2 (ja) | コンクリート型枠 | |
JP2020093198A (ja) | 複層塗膜形成方法 | |
KR100432211B1 (ko) | 내열성이우수한광경화형불소변성우레탄아크릴레이트올리고머의제조방법 | |
TWI839605B (zh) | 接著劑用樹脂組成物、接著劑及接著構造體 | |
JP2019044010A (ja) | 親水性コーティング用樹脂組成物 | |
JP2024506947A (ja) | 耐油性及び接着性が向上した金属用コーティング組成物及びその製造方法、並びにその組成物でコーティングされた金属物品 | |
CN115873203A (zh) | 高耐磨单组分水性聚氨酯及其乳液或分散体、涂层的制备方法及应用 | |
US20210317254A1 (en) | Polymeric material including a uretdione-containing material and an epoxy component, two-part compositions, and methods |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20211215 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20221011 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20221013 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20221201 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20230203 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20230606 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20230825 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20230901 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20231128 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20231211 |
|
R151 | Written notification of patent or utility model registration |
Ref document number: 7413649 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R151 |