CA1337093C - Acrylic modified reactive urethane hot melt adhesive compositions - Google Patents
Acrylic modified reactive urethane hot melt adhesive compositionsInfo
- Publication number
- CA1337093C CA1337093C CA000536315A CA536315A CA1337093C CA 1337093 C CA1337093 C CA 1337093C CA 000536315 A CA000536315 A CA 000536315A CA 536315 A CA536315 A CA 536315A CA 1337093 C CA1337093 C CA 1337093C
- Authority
- CA
- Canada
- Prior art keywords
- diisocyanate
- hot melt
- adhesive composition
- melt adhesive
- isocyanate
- 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.)
- Expired - Fee Related
Links
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 239000004831 Hot glue Substances 0.000 title claims abstract description 37
- 239000000203 mixture Substances 0.000 title claims description 47
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title description 6
- 239000012948 isocyanate Substances 0.000 claims abstract description 53
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 53
- 229920000642 polymer Polymers 0.000 claims abstract description 36
- 239000000178 monomer Substances 0.000 claims abstract description 31
- 239000004014 plasticizer Substances 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 230000001070 adhesive effect Effects 0.000 claims description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 40
- 239000000853 adhesive Substances 0.000 claims description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- -1 ether glycols Chemical class 0.000 claims description 25
- 239000007787 solid Substances 0.000 claims description 25
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- 229920005862 polyol Polymers 0.000 claims description 22
- 150000003077 polyols Chemical class 0.000 claims description 22
- 239000005056 polyisocyanate Substances 0.000 claims description 16
- 229920001228 polyisocyanate Polymers 0.000 claims description 16
- 239000012943 hotmelt Substances 0.000 claims description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 14
- 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 13
- 239000004814 polyurethane Substances 0.000 claims description 13
- 229920002635 polyurethane Polymers 0.000 claims description 13
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 9
- 239000005977 Ethylene Substances 0.000 claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- 125000005442 diisocyanate group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000012643 polycondensation polymerization Methods 0.000 claims description 8
- 238000010526 radical polymerization reaction Methods 0.000 claims description 7
- 150000002009 diols Chemical class 0.000 claims description 6
- 150000002170 ethers Chemical class 0.000 claims description 6
- 229920001281 polyalkylene Polymers 0.000 claims description 6
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 5
- 229920000728 polyester Polymers 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 238000012546 transfer Methods 0.000 claims description 4
- XXMCAWSEVMOGLO-UHFFFAOYSA-N 1,1-dichloro-1,6-diisocyanatohexane Chemical compound O=C=NC(Cl)(Cl)CCCCCN=C=O XXMCAWSEVMOGLO-UHFFFAOYSA-N 0.000 claims description 3
- WOGVOIWHWZWYOZ-UHFFFAOYSA-N 1,1-diisocyanatoethane Chemical compound O=C=NC(C)N=C=O WOGVOIWHWZWYOZ-UHFFFAOYSA-N 0.000 claims description 3
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 claims description 3
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 claims description 3
- ZGDSDWSIFQBAJS-UHFFFAOYSA-N 1,2-diisocyanatopropane Chemical compound O=C=NC(C)CN=C=O ZGDSDWSIFQBAJS-UHFFFAOYSA-N 0.000 claims description 3
- PFUKECZPRROVOD-UHFFFAOYSA-N 1,3,5-triisocyanato-2-methylbenzene Chemical compound CC1=C(N=C=O)C=C(N=C=O)C=C1N=C=O PFUKECZPRROVOD-UHFFFAOYSA-N 0.000 claims description 3
- PQDIQKXGPYOGDI-UHFFFAOYSA-N 1,3,5-triisocyanatobenzene Chemical compound O=C=NC1=CC(N=C=O)=CC(N=C=O)=C1 PQDIQKXGPYOGDI-UHFFFAOYSA-N 0.000 claims description 3
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 claims description 3
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 claims description 3
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical class CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- 150000002688 maleic acid derivatives Chemical class 0.000 claims 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 claims description 3
- 229920001567 vinyl ester resin Polymers 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims 5
- 239000012467 final product Substances 0.000 claims 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- ISNRCPCOXSJZRZ-UHFFFAOYSA-N 1-benzhydryl-2,3,4-triisocyanatobenzene Chemical compound N(=C=O)C1=C(C(=C(C=C1)C(C1=CC=CC=C1)C1=CC=CC=C1)N=C=O)N=C=O ISNRCPCOXSJZRZ-UHFFFAOYSA-N 0.000 claims 1
- RJLZSKYNYLYCNY-UHFFFAOYSA-N ethyl carbamate;isocyanic acid Chemical compound N=C=O.CCOC(N)=O RJLZSKYNYLYCNY-UHFFFAOYSA-N 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 230000032683 aging Effects 0.000 abstract description 5
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 22
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 17
- 238000012360 testing method Methods 0.000 description 17
- 239000004615 ingredient Substances 0.000 description 14
- 239000004342 Benzoyl peroxide Substances 0.000 description 13
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 13
- 235000019400 benzoyl peroxide Nutrition 0.000 description 13
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- 229920002799 BoPET Polymers 0.000 description 12
- 239000005041 Mylar™ Substances 0.000 description 12
- 229920001451 polypropylene glycol Polymers 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 229920002554 vinyl polymer Polymers 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 7
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 7
- 239000011888 foil Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000004698 Polyethylene Substances 0.000 description 5
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- UTWCLCFHXYGTTF-UHFFFAOYSA-N 2,2-dimethyl-1-phenylpropane-1,3-diol Chemical compound OCC(C)(C)C(O)C1=CC=CC=C1 UTWCLCFHXYGTTF-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000012986 chain transfer agent Substances 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- MQJLQLWFHRDQJT-UHFFFAOYSA-N CC(C(O)=O)=C.N=C=O.N=C=O.OC(CCCCC(O)=O)=O Chemical compound CC(C(O)=O)=C.N=C=O.N=C=O.OC(CCCCC(O)=O)=O MQJLQLWFHRDQJT-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000001627 detrimental effect Effects 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000003475 lamination Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 229920006389 polyphenyl polymer Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005992 thermoplastic resin Polymers 0.000 description 3
- YRTNMMLRBJMGJJ-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol;hexanedioic acid Chemical compound OCC(C)(C)CO.OC(=O)CCCCC(O)=O YRTNMMLRBJMGJJ-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 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
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- PAUHLEIGHAUFAK-UHFFFAOYSA-N 1-isocyanato-1-[(1-isocyanatocyclohexyl)methyl]cyclohexane Chemical compound C1CCCCC1(N=C=O)CC1(N=C=O)CCCCC1 PAUHLEIGHAUFAK-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 1
- 235000007173 Abies balsamea Nutrition 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 239000004857 Balsam Substances 0.000 description 1
- XUPWCZXDMJWVJJ-UHFFFAOYSA-N C(C1=C(C=CC=C1)N=C=O)C1=C(C=CC=C1)N=C=O.C(CCCCC(=O)O)(=O)O.OCC(C)(CO)C Chemical compound C(C1=C(C=CC=C1)N=C=O)C1=C(C=CC=C1)N=C=O.C(CCCCC(=O)O)(=O)O.OCC(C)(CO)C XUPWCZXDMJWVJJ-UHFFFAOYSA-N 0.000 description 1
- 101100080971 Caenorhabditis elegans cps-6 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 244000018716 Impatiens biflora Species 0.000 description 1
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
- 102100035115 Testin Human genes 0.000 description 1
- 101710070533 Testin Proteins 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- VXTQKJXIZHSXBY-UHFFFAOYSA-N butan-2-yl 2-methylprop-2-enoate Chemical compound CCC(C)OC(=O)C(C)=C VXTQKJXIZHSXBY-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010382 chemical cross-linking Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85953986A | 1986-05-05 | 1986-05-05 | |
| US859,539 | 1986-05-05 | ||
| US4314087A | 1987-04-30 | 1987-04-30 | |
| US043,140 | 1987-04-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1337093C true CA1337093C (en) | 1995-09-19 |
Family
ID=26720086
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000536315A Expired - Fee Related CA1337093C (en) | 1986-05-05 | 1987-05-04 | Acrylic modified reactive urethane hot melt adhesive compositions |
Country Status (7)
| Country | Link |
|---|---|
| JP (2) | JPH064840B2 (fi) |
| KR (1) | KR900004705B1 (fi) |
| AU (1) | AU584507B2 (fi) |
| CA (1) | CA1337093C (fi) |
| DK (1) | DK165698C (fi) |
| FI (1) | FI91081C (fi) |
| MX (1) | MX173416B (fi) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7612151B2 (en) | 2004-04-09 | 2009-11-03 | Dainippon Ink And Chemicals, Inc. | Moisture-curable polyurethane hot-melt adhesive |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH666899A5 (de) * | 1986-05-09 | 1988-08-31 | Sika Ag | Reaktiver schmelzklebstoff. |
| JP2539814B2 (ja) * | 1987-03-06 | 1996-10-02 | 旭硝子株式会社 | 接着剤組成物の製造方法 |
| US4786657A (en) * | 1987-07-02 | 1988-11-22 | Minnesota Mining And Manufacturing Company | Polyurethanes and polyurethane/polyureas crosslinked using 2-glyceryl acrylate or 2-glyceryl methacrylate |
| JP2705855B2 (ja) * | 1991-05-10 | 1998-01-28 | 日本エヌエスシー株式会社 | 接着剤組成物 |
| JP2004279470A (ja) * | 2003-03-12 | 2004-10-07 | Osaka Sealing Printing Co Ltd | 装着ラベル |
| US8664330B2 (en) * | 2003-04-04 | 2014-03-04 | Henkel US IP LLC | Reactive hot melt adhesive with improved hydrolysis resistance |
| KR100771858B1 (ko) * | 2004-07-13 | 2007-11-01 | 삼성전자주식회사 | 정지 전류 및 출력 전류의 제어가 용이한 ａｂ급 증폭 회로 |
| JP5757707B2 (ja) | 2010-08-26 | 2015-07-29 | ヘンケルジャパン株式会社 | 湿気硬化型ホットメルト接着剤 |
| DE102010041854A1 (de) * | 2010-10-01 | 2012-04-05 | Henkel Ag & Co. Kgaa | Polyurethan-Schmelzklebstoff aus Polyacrylaten und Polyestern |
| JP5734092B2 (ja) | 2011-05-24 | 2015-06-10 | ヘンケルジャパン株式会社 | 湿気硬化型ホットメルト接着剤 |
| KR20140067366A (ko) * | 2012-11-26 | 2014-06-05 | 박희대 | 에폭시 접착용 핫멜트 필름의 조성물 |
| JPWO2015016029A1 (ja) * | 2013-07-31 | 2017-03-02 | 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 |
| KR20170029429A (ko) * | 2014-07-02 | 2017-03-15 | 요코하마 고무 가부시키가이샤 | 반응성 핫멜트 접착제 조성물 |
| JP6408036B2 (ja) | 2014-07-02 | 2018-10-17 | ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェンＨｅｎｋｅｌ ＡＧ ＆ Ｃｏ． ＫＧａＡ | 除去可能なポリウレタンホットメルト接着剤およびその使用 |
| JP6662376B2 (ja) * | 2015-03-30 | 2020-03-11 | 日立化成株式会社 | 反応性ホットメルト接着剤組成物 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5130898B2 (fi) * | 1973-01-11 | 1976-09-03 | ||
| JPS5147735B2 (fi) * | 1974-03-15 | 1976-12-16 | ||
| JPS5237936A (en) * | 1975-09-19 | 1977-03-24 | Mitsubishi Petrochem Co Ltd | Reactive hot-melt adhesive |
| JPS52123436A (en) * | 1976-04-08 | 1977-10-17 | Mitsubishi Petrochem Co Ltd | Reactive hot-melt adhesive |
| JPS5321236A (en) * | 1976-08-10 | 1978-02-27 | Mitsubishi Petrochem Co Ltd | Reactive hot-melt adhesives |
| US4332716A (en) * | 1980-12-10 | 1982-06-01 | Union Carbide Corporation | Polymer/polyisocyanate compositions, processes for making same and processes for making polyurethane products therefrom |
| GB2151643B (en) * | 1983-12-22 | 1987-02-11 | Bostik Ltd | Heat curable compositions |
| US4539345A (en) * | 1985-02-04 | 1985-09-03 | Minnesota Mining And Manufacturing Company | Moisture-curable polyurethane composition |
-
1987
- 1987-05-04 FI FI871966A patent/FI91081C/fi not_active IP Right Cessation
- 1987-05-04 DK DK226787A patent/DK165698C/da not_active IP Right Cessation
- 1987-05-04 CA CA000536315A patent/CA1337093C/en not_active Expired - Fee Related
- 1987-05-04 KR KR1019870004436A patent/KR900004705B1/ko not_active Expired
- 1987-05-04 MX MX006324A patent/MX173416B/es unknown
- 1987-05-05 AU AU72503/87A patent/AU584507B2/en not_active Expired
- 1987-05-06 JP JP62109065A patent/JPH064840B2/ja not_active Expired - Lifetime
-
1991
- 1991-06-25 JP JP3153194A patent/JPH0678515B2/ja not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7612151B2 (en) | 2004-04-09 | 2009-11-03 | Dainippon Ink And Chemicals, Inc. | Moisture-curable polyurethane hot-melt adhesive |
Also Published As
| Publication number | Publication date |
|---|---|
| FI91081B (fi) | 1994-01-31 |
| JPH05311145A (ja) | 1993-11-22 |
| JPH0678515B2 (ja) | 1994-10-05 |
| KR900004705B1 (ko) | 1990-07-02 |
| DK226787A (da) | 1987-11-06 |
| KR870011212A (ko) | 1987-12-21 |
| AU7250387A (en) | 1987-11-26 |
| DK165698B (da) | 1993-01-04 |
| DK226787D0 (da) | 1987-05-04 |
| JPS636076A (ja) | 1988-01-12 |
| FI871966L (fi) | 1987-11-06 |
| AU584507B2 (en) | 1989-05-25 |
| FI871966A0 (fi) | 1987-05-04 |
| JPH064840B2 (ja) | 1994-01-19 |
| DK165698C (da) | 1993-06-07 |
| MX173416B (es) | 1994-03-03 |
| FI91081C (fi) | 1994-05-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |