CA2685304C - Moisture curable polyurethane hot melt adhesive composition - Google Patents
Moisture curable polyurethane hot melt adhesive composition Download PDFInfo
- Publication number
- CA2685304C CA2685304C CA2685304A CA2685304A CA2685304C CA 2685304 C CA2685304 C CA 2685304C CA 2685304 A CA2685304 A CA 2685304A CA 2685304 A CA2685304 A CA 2685304A CA 2685304 C CA2685304 C CA 2685304C
- Authority
- CA
- Canada
- Prior art keywords
- adhesive composition
- weight
- substrate
- styrene
- hot melt
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 72
- 239000004831 Hot glue Substances 0.000 title claims abstract description 19
- 229920002635 polyurethane Polymers 0.000 title claims description 11
- 239000004814 polyurethane Substances 0.000 title claims description 11
- 229920005906 polyester polyol Polymers 0.000 claims abstract description 34
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims abstract description 31
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229920005989 resin Polymers 0.000 claims abstract description 15
- 239000011347 resin Substances 0.000 claims abstract description 15
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 14
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 12
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 12
- 238000002844 melting Methods 0.000 claims abstract description 8
- 230000008018 melting Effects 0.000 claims abstract description 8
- 230000001070 adhesive effect Effects 0.000 claims description 59
- 239000000853 adhesive Substances 0.000 claims description 58
- 239000000758 substrate Substances 0.000 claims description 32
- -1 polysiloxanes Polymers 0.000 claims description 25
- 229920005862 polyol Polymers 0.000 claims description 23
- 150000003077 polyols Chemical class 0.000 claims description 22
- 239000002023 wood Substances 0.000 claims description 15
- 239000002184 metal Substances 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 229920001577 copolymer Polymers 0.000 claims description 9
- 239000005038 ethylene vinyl acetate Substances 0.000 claims description 9
- 150000002739 metals Chemical class 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 8
- 239000000194 fatty acid Substances 0.000 claims description 8
- 229930195729 fatty acid Natural products 0.000 claims description 8
- 150000004665 fatty acids Chemical class 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 7
- 229920002430 Fibre-reinforced plastic Polymers 0.000 claims description 6
- 239000011151 fibre-reinforced plastic Substances 0.000 claims description 6
- 239000000155 melt Substances 0.000 claims description 6
- 239000004793 Polystyrene Substances 0.000 claims description 5
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 claims description 5
- 239000002131 composite material Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 229920002223 polystyrene Polymers 0.000 claims description 5
- 239000004800 polyvinyl chloride Substances 0.000 claims description 5
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 claims description 4
- 239000004417 polycarbonate Substances 0.000 claims description 4
- 229920000515 polycarbonate Polymers 0.000 claims description 4
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 claims description 4
- FACXGONDLDSNOE-UHFFFAOYSA-N buta-1,3-diene;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 FACXGONDLDSNOE-UHFFFAOYSA-N 0.000 claims description 3
- 229920006248 expandable polystyrene Polymers 0.000 claims description 3
- 230000009477 glass transition Effects 0.000 claims description 3
- 229920002614 Polyether block amide Polymers 0.000 claims description 2
- 229920000058 polyacrylate Polymers 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims 1
- 239000004642 Polyimide Substances 0.000 claims 1
- 229920002367 Polyisobutene Polymers 0.000 claims 1
- 229920005549 butyl rubber Polymers 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 229920002401 polyacrylamide Polymers 0.000 claims 1
- 229920002239 polyacrylonitrile Polymers 0.000 claims 1
- 229920013639 polyalphaolefin Polymers 0.000 claims 1
- 229920002647 polyamide Polymers 0.000 claims 1
- 229920001721 polyimide Polymers 0.000 claims 1
- 229920000193 polymethacrylate Polymers 0.000 claims 1
- 229920000098 polyolefin Polymers 0.000 claims 1
- 229920001296 polysiloxane Polymers 0.000 claims 1
- 229920003048 styrene butadiene rubber Polymers 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 description 18
- 239000002253 acid Substances 0.000 description 9
- 239000012943 hotmelt Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 6
- 238000010998 test method Methods 0.000 description 6
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 5
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000000539 dimer Substances 0.000 description 5
- 229920006270 hydrocarbon resin Polymers 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229920001400 block copolymer Polymers 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 239000003209 petroleum derivative Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 description 3
- 150000003505 terpenes Chemical class 0.000 description 3
- 235000007586 terpenes Nutrition 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZMSQJSMSLXVTKN-UHFFFAOYSA-N 4-[2-(2-morpholin-4-ylethoxy)ethyl]morpholine Chemical compound C1COCCN1CCOCCN1CCOCC1 ZMSQJSMSLXVTKN-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000013032 Hydrocarbon resin Substances 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 230000001143 conditioned effect Effects 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000003348 petrochemical agent Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229920006132 styrene block copolymer Polymers 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- JIABEENURMZTTI-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatophenyl)methyl]benzene Chemical compound O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O JIABEENURMZTTI-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VHOQXEIFYTTXJU-UHFFFAOYSA-N Isobutylene-isoprene copolymer Chemical compound CC(C)=C.CC(=C)C=C VHOQXEIFYTTXJU-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- IIGAAOXXRKTFAM-UHFFFAOYSA-N N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C Chemical compound N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C IIGAAOXXRKTFAM-UHFFFAOYSA-N 0.000 description 1
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical class N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 1
- 241000845082 Panama Species 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 1
- 229920002522 Wood fibre Polymers 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 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
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001343 alkyl silanes Chemical class 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000006664 bond formation reaction Methods 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- JFAGGQWDKLJPHC-UHFFFAOYSA-N butyl prop-2-enoate;carbon monoxide;ethene Chemical compound O=[C].C=C.CCCCOC(=O)C=C JFAGGQWDKLJPHC-UHFFFAOYSA-N 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000919 ceramic Substances 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
- 239000004927 clay Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical class O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 229920006228 ethylene acrylate copolymer Polymers 0.000 description 1
- 229920006225 ethylene-methyl acrylate Polymers 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005594 polymer fiber Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920005996 polystyrene-poly(ethylene-butylene)-polystyrene Polymers 0.000 description 1
- 150000003097 polyterpenes Chemical class 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- 229920006216 polyvinyl aromatic Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002025 wood fiber Substances 0.000 description 1
- 239000010457 zeolite Substances 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
- C09J175/06—Polyurethanes from polyesters
-
- 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
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
- C08G18/2825—Alkanols, cycloalkanols or arylalkanols including terpenealcohols having at least 6 carbon atoms
-
- 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
- C08G18/42—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
- C08G18/423—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing cycloaliphatic groups
- C08G18/4233—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing cycloaliphatic groups derived from polymerised higher fatty acids or alcohols
-
- 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
-
- 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
- C09J2475/00—Presence of polyurethane
-
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/935—Hot melt adhesive
-
- 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
- Y10T428/12—All metal or with adjacent metals
- Y10T428/12493—Composite; i.e., plural, adjacent, spatially distinct metal components [e.g., layers, joint, etc.]
- Y10T428/12535—Composite; i.e., plural, adjacent, spatially distinct metal components [e.g., layers, joint, etc.] with additional, spatially distinct nonmetal component
- Y10T428/12556—Organic component
- Y10T428/12569—Synthetic resin
-
- 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]
- Y10T428/31547—Of polyisocyanurate
-
- 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.]
-
- 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.]
- Y10T428/31573—Next to addition polymer of ethylenically unsaturated monomer
- Y10T428/3158—Halide monomer type [polyvinyl chloride, etc.]
-
- 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.]
- Y10T428/31573—Next to addition polymer of ethylenically unsaturated monomer
- Y10T428/31587—Hydrocarbon polymer [polyethylene, polybutadiene, etc.]
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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/805,777 | 2007-05-24 | ||
| US11/805,777 US7914895B2 (en) | 2007-05-24 | 2007-05-24 | Moisture curable hot melt adhesive composition |
| PCT/US2008/064474 WO2008147845A1 (en) | 2007-05-24 | 2008-05-22 | Moisture curable polyurethane hot melt adhesive composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2685304A1 CA2685304A1 (en) | 2008-12-04 |
| CA2685304C true CA2685304C (en) | 2015-04-07 |
Family
ID=39683553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2685304A Expired - Fee Related CA2685304C (en) | 2007-05-24 | 2008-05-22 | Moisture curable polyurethane hot melt adhesive composition |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7914895B2 (OSRAM) |
| EP (1) | EP2158240A1 (OSRAM) |
| JP (1) | JP4801219B2 (OSRAM) |
| KR (1) | KR101179003B1 (OSRAM) |
| CN (1) | CN101679581B (OSRAM) |
| AU (1) | AU2008256892B2 (OSRAM) |
| BR (1) | BRPI0811012A2 (OSRAM) |
| CA (1) | CA2685304C (OSRAM) |
| MX (1) | MX2009011133A (OSRAM) |
| WO (1) | WO2008147845A1 (OSRAM) |
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| KR100927550B1 (ko) * | 2009-05-06 | 2009-11-20 | (주)폴머 | 성형성이 개선된 스킨층을 갖는 발포 폴리스티렌 입자와 이를 이용한 폴리스티렌 발포 성형물 |
| KR101752514B1 (ko) | 2009-06-05 | 2017-06-29 | 바스프 에스이 | 소성 변형성 강성 폴리우레탄 발포체, 접착제 및 피복재를 함유하는 복합 부품 |
| CN102051152A (zh) * | 2009-11-09 | 2011-05-11 | 上海天希化工有限公司 | 一种活性热熔性粘合剂及其制备方法 |
| JP5445223B2 (ja) * | 2010-03-02 | 2014-03-19 | 東洋アドレ株式会社 | 湿気硬化型接着剤組成物 |
| WO2012010558A1 (en) | 2010-07-22 | 2012-01-26 | Construction Research & Technology Gmbh | Reduction in modulus of polyurethane sealants and adhesives |
| CN103052666A (zh) | 2010-07-22 | 2013-04-17 | 建筑研究和技术有限公司 | 使用绿色预聚合物的密封剂和胶粘剂 |
| CN102010687B (zh) * | 2010-10-28 | 2013-04-17 | 华南理工大学 | 一种快速固化反应型热熔胶及其制备方法 |
| CA2834866C (en) * | 2011-05-12 | 2019-06-11 | H.B. Fuller Company | Hot melt moisture cure adhesive compositions |
| TWI534165B (zh) * | 2011-10-24 | 2016-05-21 | 迪愛生股份有限公司 | 濕氣硬化型聚胺基甲酸酯熱熔樹脂組成物、接著劑及物品 |
| WO2013138350A1 (en) * | 2012-03-12 | 2013-09-19 | Ifs Industries Inc | Reactive hot melt |
| CN103360762B (zh) * | 2012-03-27 | 2017-07-18 | 富士施乐株式会社 | 树脂材料、环形带、辊、图像定影单元以及成像装置 |
| WO2013148506A1 (en) * | 2012-03-30 | 2013-10-03 | 3M Innovative Properties Company | Urea-based and urethane-based pressure sensitive adhesive blends |
| JP5989432B2 (ja) * | 2012-07-18 | 2016-09-07 | 日東電工株式会社 | 塗膜保護シート |
| EP2712879B1 (de) * | 2012-09-28 | 2018-02-14 | Collano Adhesives AG | Latent reaktive Schmelzklebstoffzusammensetzung |
| WO2014059424A2 (en) | 2012-10-12 | 2014-04-17 | High Voltage Graphics, Inc. | Flexible heat sealable decorative articles and method for making the same |
| CN104884492B (zh) * | 2012-10-31 | 2017-11-28 | 路博润先进材料公司 | 具有结晶链端的热塑性聚氨酯 |
| CN102977811A (zh) * | 2012-11-21 | 2013-03-20 | 深圳长园电子材料有限公司 | 一种双壁热缩套管用无卤复合热熔胶及其制备方法 |
| KR20140067366A (ko) * | 2012-11-26 | 2014-06-05 | 박희대 | 에폭시 접착용 핫멜트 필름의 조성물 |
| EP2970584B1 (en) * | 2013-03-15 | 2020-12-30 | Firestone Building Products Co., LLC | Bonding adhesive and adhered roofing systems prepared using the same |
| US11686094B2 (en) | 2013-03-15 | 2023-06-27 | Holcim Technology Ltd | Bonding adhesive and adhered roofing systems prepared using the same |
| CN105229049A (zh) * | 2013-05-22 | 2016-01-06 | 路博润先进材料公司 | 由具有结晶链端的热塑性聚氨酯制备的制品 |
| JP5711783B2 (ja) * | 2013-06-07 | 2015-05-07 | 株式会社エナテック | 基板コーティング剤 |
| FR3012466B1 (fr) * | 2013-10-24 | 2015-11-13 | Bostik Sa | Psa d'origine renouvelable a pouvoir adhesif stable en temperature |
| KR101480044B1 (ko) * | 2014-03-24 | 2015-01-13 | 주식회사 오공 | 제본용 핫멜트 접착제 조성물 |
| JP6468285B2 (ja) * | 2014-04-30 | 2019-02-13 | 横浜ゴム株式会社 | １液湿気硬化型ポリウレタン組成物 |
| WO2016045074A1 (en) * | 2014-09-26 | 2016-03-31 | Henkel (China) Investment Co. Ltd. | A reactive polyurethane hot melt adhesive and the use thereof |
| WO2016138445A1 (en) * | 2015-02-27 | 2016-09-01 | H.B. Fuller Company | Oily chemical resistant moisture curable hot melt adhesive compositions and articles including the same |
| US20160280977A1 (en) * | 2015-03-24 | 2016-09-29 | IFS Industries Inc. | Two-Part Urethane Adhesive |
| DE102015106982A1 (de) * | 2015-05-05 | 2016-11-10 | Lisa Dräxlmaier GmbH | Zeolithhaltige Heißschmelzklebe-, Heißschmelzdicht- und Heißklebebeschichtungsmassen |
| CN105238009B (zh) * | 2015-10-09 | 2017-12-15 | 滁州环球聚氨酯科技有限公司 | 一种高强度耐磨耐油聚氨酯弹性体 |
| CN105111969A (zh) * | 2015-10-17 | 2015-12-02 | 霍进铭 | 一种环保热熔胶的制作方法 |
| CN105694795B (zh) * | 2016-01-28 | 2020-04-07 | 苏州科逸住宅设备股份有限公司 | 整体浴室用墙板及其制备方法 |
| US11207919B2 (en) | 2016-06-21 | 2021-12-28 | Bridgestone Americas Tire Operations, Llc | Methods for treating inner liner surface, inner liners resulting therefrom and tires containing such inner liners |
| CN109415480A (zh) * | 2016-06-27 | 2019-03-01 | 路博润先进材料公司 | 具有降低的粘性的热塑性聚氨酯 |
| WO2018005810A1 (en) | 2016-06-30 | 2018-01-04 | Bridgestone Americas Tire Operations, Llc | Methods for treating inner liners, inner liners resulting therefrom and tires containing such inner liners |
| JP6848062B2 (ja) | 2016-12-15 | 2021-03-24 | ブリヂストン アメリカズ タイヤ オペレーションズ、 エルエルシー | 硬化したインナーライナー上にポリマー含有コーティングを生成する方法、かかるインナーライナーを含むタイヤを製造する方法、及びかかるインナーライナーを含むタイヤ |
| CN110214076A (zh) | 2016-12-15 | 2019-09-06 | 普利司通美国轮胎运营有限责任公司 | 含有密封剂的轮胎和相关方法 |
| JP6961697B2 (ja) | 2016-12-15 | 2021-11-05 | ブリヂストン アメリカズ タイヤ オペレーションズ、 エルエルシー | バリアを有するシーラント層、それを含有するタイヤ、及び関連するプロセス |
| FR3069551B1 (fr) * | 2017-07-28 | 2020-08-07 | Bostik Sa | Composition adhesive reticulable par chauffage |
| CN107972334A (zh) * | 2017-11-21 | 2018-05-01 | 安徽美湖新材料科技有限公司 | 医用纺织品材料及其制备方法与应用 |
| CN107841274A (zh) * | 2017-11-21 | 2018-03-27 | 上海天洋热熔粘接材料股份有限公司 | 湿固化聚氨酯热熔胶的制备工艺 |
| CN108467705A (zh) * | 2018-02-13 | 2018-08-31 | 嘉兴市建川新材料科技有限公司 | 一种高初粘力的湿固化聚氨酯热熔胶及制备方法 |
| CN111741992B (zh) * | 2018-02-21 | 2022-10-28 | Dic株式会社 | 湿气固化型聚氨酯热熔树脂组合物 |
| US11541649B2 (en) | 2018-09-19 | 2023-01-03 | Carefusion 303, Inc. | Methods and formulations for bonding dissimilar materials |
| EP3891205B1 (en) | 2018-12-06 | 2024-08-28 | Eastman Chemical (China) Co., Ltd. | Polyesters comprising 2, 2, 4, 4-tetraalkyl-1, 3-cyclobutanediol |
| CN109971409B (zh) * | 2019-04-01 | 2020-05-19 | 泉州新华福合成材料有限公司 | 一种聚氨酯密封胶及其应用 |
| US12331192B2 (en) | 2019-04-05 | 2025-06-17 | Sika Technology Ag | Dimer fatty acid-polyester diol-based polymer, containing isocyanate groups |
| CN110093135A (zh) * | 2019-05-14 | 2019-08-06 | 永隆高新科技(青岛)有限公司 | 一种适用于超低温的密度板用聚氨酯胶粘剂 |
| MX2021014779A (es) | 2019-06-25 | 2022-01-18 | Fuller H B Co | Composicion adhesiva termofusible de poliuretano curable por humedad que tiene niveles bajos de monomero de diisocianato. |
| EP4021706A1 (en) * | 2019-08-26 | 2022-07-06 | H.B. Fuller Company | Fast set moisture curable hot melt adhesive composition and articles including the same |
| KR20220157406A (ko) * | 2020-04-02 | 2022-11-29 | 헨켈 아게 운트 코. 카게아아 | 올레산 내화학성을 갖는 수분-경화성 폴리우레탄 핫 멜트 접착제 조성물 |
| TWI768427B (zh) * | 2020-08-07 | 2022-06-21 | 日勝化工股份有限公司 | 熱熔型反應性聚氨酯接著劑 |
| WO2022093670A1 (en) * | 2020-10-26 | 2022-05-05 | Lord Corporation | Semi-cyrstalline two-part polyurethane adhesives from amorphous components |
| US20240343957A1 (en) * | 2021-08-20 | 2024-10-17 | Dow Global Technologies Llc | High green strength reactive hot melt adhesives |
| CN118613563A (zh) * | 2022-01-07 | 2024-09-06 | 汉高股份有限及两合公司 | 反应性热熔粘合剂组合物及其用途 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1290489A (OSRAM) | 1968-12-02 | 1972-09-27 | ||
| GB2137638A (en) | 1983-04-05 | 1984-10-10 | Bostik Ltd | Adhesive compositions |
| US4808255A (en) | 1987-05-07 | 1989-02-28 | H. B. Fuller Company | Thermally stable reactive hot melt urethane adhesive composition having a thermoplastic polymer, a compatible, curing urethane polyester polyol prepolymer and a tackifying agent |
| US5418310A (en) | 1990-04-27 | 1995-05-23 | Minnesota Mining And Manufacturing Company | Mixture of isocyanate-terminated polyurethane prepolymers having good adhesion |
| US5472785A (en) | 1994-04-12 | 1995-12-05 | Minnesota Mining And Manufacturing Company | Reactive wax-containing moisture curable hot melt composition |
| JPH08225780A (ja) * | 1995-02-20 | 1996-09-03 | Sekisui Chem Co Ltd | ウレタン系水性接着剤組成物 |
| US6355317B1 (en) * | 1997-06-19 | 2002-03-12 | H. B. Fuller Licensing & Financing, Inc. | Thermoplastic moisture cure polyurethanes |
| US6387449B1 (en) * | 1999-12-01 | 2002-05-14 | H. B. Fuller Licensing & Financing, Inc. | Reactive hot melt adhesive |
| JP2002179757A (ja) * | 2000-12-11 | 2002-06-26 | Toyo Ink Mfg Co Ltd | ポリウレタン複合樹脂 |
| DE10122437A1 (de) * | 2001-05-09 | 2002-11-28 | Henkel Kgaa | Schmelzklebstoff in Form eines Granulates |
| GB0207345D0 (en) | 2002-03-28 | 2002-05-08 | Unichema Chemie Bv | Polyurethane |
| JP4192544B2 (ja) * | 2002-09-27 | 2008-12-10 | 東洋インキ製造株式会社 | 無溶剤型接着剤組成物及びその利用 |
| US20060210808A1 (en) | 2002-10-15 | 2006-09-21 | Ju-Ming Hung | Reactive hot melt adhesive with non-polymeric aliphatic difunctionals |
| US7112631B2 (en) * | 2002-10-24 | 2006-09-26 | National Starch And Chemical Investment Holding Corporation | Moisture cured reactive hot melt adhesive with monofunctional reactants as grafting agents |
| US6803412B2 (en) | 2003-03-13 | 2004-10-12 | H.B. Fuller Licensing & Financing Inc. | Moisture curable hot melt sealants for glass constructions |
| JP2006037037A (ja) | 2004-07-30 | 2006-02-09 | Toyo Ink Mfg Co Ltd | 接着剤組成物 |
-
2007
- 2007-05-24 US US11/805,777 patent/US7914895B2/en not_active Expired - Fee Related
-
2008
- 2008-05-22 CN CN2008800172689A patent/CN101679581B/zh not_active Expired - Fee Related
- 2008-05-22 WO PCT/US2008/064474 patent/WO2008147845A1/en not_active Ceased
- 2008-05-22 BR BRPI0811012 patent/BRPI0811012A2/pt not_active Application Discontinuation
- 2008-05-22 EP EP08769588A patent/EP2158240A1/en not_active Withdrawn
- 2008-05-22 CA CA2685304A patent/CA2685304C/en not_active Expired - Fee Related
- 2008-05-22 JP JP2010509549A patent/JP4801219B2/ja not_active Expired - Fee Related
- 2008-05-22 KR KR1020097023424A patent/KR101179003B1/ko not_active Expired - Fee Related
- 2008-05-22 AU AU2008256892A patent/AU2008256892B2/en not_active Ceased
- 2008-05-22 MX MX2009011133A patent/MX2009011133A/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0811012A2 (pt) | 2015-01-27 |
| AU2008256892A1 (en) | 2008-12-04 |
| CA2685304A1 (en) | 2008-12-04 |
| KR101179003B1 (ko) | 2012-09-03 |
| CN101679581B (zh) | 2013-11-13 |
| JP2010528160A (ja) | 2010-08-19 |
| AU2008256892B2 (en) | 2013-08-22 |
| CN101679581A (zh) | 2010-03-24 |
| MX2009011133A (es) | 2009-10-30 |
| KR20100009570A (ko) | 2010-01-27 |
| US7914895B2 (en) | 2011-03-29 |
| US20080292902A1 (en) | 2008-11-27 |
| WO2008147845A1 (en) | 2008-12-04 |
| JP4801219B2 (ja) | 2011-10-26 |
| EP2158240A1 (en) | 2010-03-03 |
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