EP3704173A1 - Reactive adhesives based on block copolymers - Google Patents
Reactive adhesives based on block copolymersInfo
- Publication number
- EP3704173A1 EP3704173A1 EP18796040.6A EP18796040A EP3704173A1 EP 3704173 A1 EP3704173 A1 EP 3704173A1 EP 18796040 A EP18796040 A EP 18796040A EP 3704173 A1 EP3704173 A1 EP 3704173A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- titanium
- polybutadiene
- diisocyanate
- mole percent
- diphenylmethane diisocyanate
- 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.)
- Pending
Links
- 229920001400 block copolymer Polymers 0.000 title claims abstract description 39
- 239000004823 Reactive adhesive Substances 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims abstract description 66
- 229920002857 polybutadiene Polymers 0.000 claims abstract description 38
- 229920000098 polyolefin Polymers 0.000 claims abstract description 35
- 239000010936 titanium Substances 0.000 claims abstract description 33
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 32
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 32
- 239000005062 Polybutadiene Substances 0.000 claims abstract description 31
- 229920005862 polyol Polymers 0.000 claims abstract description 27
- 150000003077 polyols Chemical class 0.000 claims abstract description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 24
- -1 isocyanate compound Chemical class 0.000 claims abstract description 24
- 239000000758 substrate Substances 0.000 claims abstract description 17
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 15
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 15
- 239000012948 isocyanate Substances 0.000 claims abstract description 15
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 15
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 26
- 239000000178 monomer Substances 0.000 claims description 21
- 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 16
- 238000000034 method Methods 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000000853 adhesive Substances 0.000 claims description 13
- 230000001070 adhesive effect Effects 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 11
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 11
- 229920000728 polyester Polymers 0.000 claims description 10
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims description 9
- 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 claims description 8
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000002009 diols Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- RYSXWUYLAWPLES-MTOQALJVSA-N (Z)-4-hydroxypent-3-en-2-one titanium Chemical compound [Ti].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O RYSXWUYLAWPLES-MTOQALJVSA-N 0.000 claims description 4
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- ITNVWQNWHXEMNS-UHFFFAOYSA-N methanolate;titanium(4+) Chemical compound [Ti+4].[O-]C.[O-]C.[O-]C.[O-]C ITNVWQNWHXEMNS-UHFFFAOYSA-N 0.000 claims description 4
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 claims description 4
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 claims description 4
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 4
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 238000004132 cross linking Methods 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- GRWPYGBKJYICOO-UHFFFAOYSA-N 2-methylpropan-2-olate;titanium(4+) Chemical compound [Ti+4].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] GRWPYGBKJYICOO-UHFFFAOYSA-N 0.000 claims 2
- 238000013016 damping Methods 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 239000004721 Polyphenylene oxide Substances 0.000 description 8
- 229920000570 polyether Polymers 0.000 description 8
- 229920002121 Hydroxyl-terminated polybutadiene Polymers 0.000 description 7
- 125000005442 diisocyanate group Chemical group 0.000 description 7
- 229920005906 polyester polyol Polymers 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000004831 Hot glue Substances 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 239000013466 adhesive and sealant Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000004753 textile Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000013008 moisture curing Methods 0.000 description 4
- 229920001195 polyisoprene Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 4
- 239000002023 wood Substances 0.000 description 4
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000003475 lamination Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- LOKPJYNMYCVCRM-UHFFFAOYSA-N 16-Hexadecanolide Chemical compound O=C1CCCCCCCCCCCCCCCO1 LOKPJYNMYCVCRM-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- VGHBEMPMIVEGJP-UHFFFAOYSA-N 4-methyl-2h-furan-5-one Chemical compound CC1=CCOC1=O VGHBEMPMIVEGJP-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 229920003225 polyurethane elastomer Polymers 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- 150000004072 triols Chemical class 0.000 description 2
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 description 1
- MVOSYKNQRRHGKX-UHFFFAOYSA-N 11-Undecanolactone Chemical compound O=C1CCCCCCCCCCO1 MVOSYKNQRRHGKX-UHFFFAOYSA-N 0.000 description 1
- YZRXRLLRSPQHDK-UHFFFAOYSA-N 6-Hexyltetrahydro-2H-pyran-2-one Chemical compound CCCCCCC1CCCC(=O)O1 YZRXRLLRSPQHDK-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RZTOWFMDBDPERY-UHFFFAOYSA-N Delta-Hexanolactone Chemical compound CC1CCCC(=O)O1 RZTOWFMDBDPERY-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000013032 Hydrocarbon resin Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229940123973 Oxygen scavenger Drugs 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- WNVCMFHPRIBNCW-UHFFFAOYSA-N Quercuslactone a Chemical compound CCCCC1OC(=O)CC1C WNVCMFHPRIBNCW-UHFFFAOYSA-N 0.000 description 1
- 240000002871 Tectona grandis Species 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- QOTQFLOTGBBMEX-UHFFFAOYSA-N alpha-angelica lactone Chemical compound CC1=CCC(=O)O1 QOTQFLOTGBBMEX-UHFFFAOYSA-N 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
- 238000004458 analytical method Methods 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- GSCLMSFRWBPUSK-UHFFFAOYSA-N beta-Butyrolactone Chemical compound CC1CC(=O)O1 GSCLMSFRWBPUSK-UHFFFAOYSA-N 0.000 description 1
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000003733 fiber-reinforced composite Substances 0.000 description 1
- 239000011094 fiberboard Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 1
- IPBFYZQJXZJBFQ-UHFFFAOYSA-N gamma-octalactone Chemical class CCCCC1CCC(=O)O1 IPBFYZQJXZJBFQ-UHFFFAOYSA-N 0.000 description 1
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 1
- 229920006270 hydrocarbon resin Polymers 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- LVECZGHBXXYWBO-UHFFFAOYSA-N pentadecanolide Natural products CC1CCCCCCCCCCCCC(=O)O1 LVECZGHBXXYWBO-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/222—Catalysts containing metal compounds metal compounds not provided for in groups C08G18/225 - C08G18/26
-
- 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
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/69—Polymers of conjugated dienes
- C08G18/694—Polymers of conjugated dienes containing carboxylic ester groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/69—Polymers of conjugated dienes
- C08G18/698—Mixtures with compounds of group C08G18/40
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
-
- C—CHEMISTRY; METALLURGY
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides
-
- 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
- C08G2170/00—Compositions for adhesives
- C08G2170/20—Compositions for hot melt adhesives
Definitions
- the present invention relates to a composition
- a composition comprising the reaction product of a block copolymer based on OH-functional, unhydrogenated polyolefin, preferably OH-functional polybutadiene, and cyclic esters as polyol, which has at least 1, 8 OH groups, and at least one isocyanate compound composition having at least two isocyanate groups, which is characterized in that the composition comprises 0.0001 to 40% by weight of titanium and has a content of free isocyanate groups of at least 0.1% by weight, based on the total composition Process for their preparation and the use of the composition for the production of adhesives and sealants and the use of these adhesives and sealants for bonding substrates.
- Polyester polyols are widely used today as raw materials, including for the production of adhesives and sealants.
- adhesives and sealants may be, for example, thermoplastic or reactive hot melt adhesives, 1K or 2K liquid adhesives, or epoxy systems.
- the polyols are usually reacted with an excess of diisocyanates to form reactive, moisture-curing polymers (prepolymers).
- the reactive hot melt adhesives are usually applied as a melt and have an initial strength. The reactive end groups react with the atmospheric moisture, so that the polymer hardens further and can then no longer or only with great difficulty be melted.
- Such reactive adhesive systems are characterized by rapid curing and high formulation flexibility and a wide range of applications.
- wood, textiles or metals can be bonded very well.
- a disadvantage is that very non-polar materials, such as low-energy plastics such as polyethylene or polypropylene without pretreatment of the surface, usually due to poor wetting can not be bonded to reactive hot melt adhesives based on polyesters.
- thermoplastic or silane-modified polyolefins are used for such bonds.
- the problem here is that polyolefins are not compatible or miscible with the polyester-based systems. Also, the cure of such polyolefin-based adhesives usually takes longer.
- polybutadienes can be used. Again, the problem is that polybutadienes are not compatible or miscible with polyester-based systems.
- WO 2013/177266 describes copolymers and their preparation which can be used as oxygen scavengers.
- the copolymers are preferably composed of caprolactone and hydroxy-terminated polybutadiene.
- WO 2016/026807 describes polyester-modified polybutadiene diols for the preparation of polyurethane elastomers and thermoplastic polyurethanes. These polyurethane elastomers and thermoplastic polyurethanes may e.g. processed into films, hoses or cable sheathing or used for the production of rolls, screens, filters, industrial and sports floors or adhesives. In addition, block copolymers composed of hydroxy-terminated polybutadiene and cyclic esters and their preparation are extensively described in the academic literature.
- hydroxy-functional polybutadiene with lactide (Macromolecules 2013, 46, 7387-7398) or with caprolactone (Macromolecules 2006, 39, 71 1-719) is described as a cyclic ester with a tin catalyst.
- hydroxy-terminated polybutadiene can be deprotonated by butyllithium to give the alcoholate, which subsequently polymerizes with caprolactone to form the corresponding block copolymer (e-Polymers 2009, vol 032).
- OH-functional polyolefin and hydroxy-functional polyisoprene can be used to prepare corresponding block copolymers.
- OH-functional polyisoprene and lactide using an aluminum catalyst is described (Macromol Rapid Commun. 2000, 21, 1317-1322 & Biomacromolecules 2003, 4, 216-223).
- General is the selection of possible catalysts for the polymerization of cyclic Esters via OH-functional initiators almost unlimited.
- Chem. Rev. 2004, 104, 6147-6176 describes numerous catalysts which can be used for the ring-opening polymerization of lactide or glycolide as cyclic esters.
- the object of the present invention was therefore to provide compositions which comprise the reaction product of a block copolymer based on OH-functionalized polyolefin, preferably OH-functionalized polybutadiene and cyclic esters as polyol, which has at least 1, 8 OH groups, and at least one Isocyanate compound which has at least two isocyanate groups which have a low viscosity after conversion with an excess of diisocyanate.
- the composition comprises from 0.0001% by weight to 40% by weight of titanium and has a content of free isocyanate groups of at least 0.1% by weight, based on the total composition ,
- compositions according to the invention are provided by the present invention.
- the present invention is the use of the compositions according to the invention for the production of adhesives and sealants and their use for bonding substrates as well as the use as sealants.
- compositions of the invention have the advantage that free NCO groups are present in the composition. Such free-standing NCO groups are highly reactive and elementary requirement for moisture-curing reactive adhesives.
- the compositions according to the invention also have the advantage that they have a low viscosity despite an excess of NCO groups.
- the compositions of the invention have a good processing stability, wherein the processing stability defined by the increase in viscosity at a temperature storage.
- compositions according to the invention, the inventive method for their preparation and the inventive use of the compositions are described below by way of example, without the invention being restricted to these exemplary embodiments.
- ranges, general formulas, or classes of compounds are intended to encompass not only the corresponding regions or groups of compounds explicitly mentioned, but also all sub-regions and sub-groups of compounds obtained by removing individual values (ranges) or compounds can be.
- documents are cited in the context of the present description, their content, in particular with regard to the matters referred to, should form part of the disclosure content of the present invention. If the following information is given as a percentage, it is, unless stated otherwise, in% by weight. If mean values, e.g. Molar mass averages given are, unless otherwise stated, the number average.
- the indices given may be both absolute numbers and averages, and for polymeric compounds, the indices are preferably average values.
- OH-functional polyolefins are understood as meaning polymers which are based on alkenes and / or polyenes as monomers.
- the repeating units of the polyolefins consist exclusively of the elements carbon and hydrogen and have no aromatic structures.
- the polyolefins may contain any proportion of double bonds.
- compositions according to the invention comprising at least the reaction product of a block copolymer based on OH-functional, preferably OH-terminated polyolefin, which is unhydrogenated, preferably OH-functional, preferably OH-terminated polybutadiene, which is unhydrogenated, and cyclic esters as polyol, which has at least 1, 8, preferably at least two OH groups, and at least one isocyanate compound which has at least two isocyanate groups, are characterized in that the compositions of 0.0001 to 40 wt .-%, preferably from 0.0002 to 1 wt .-% and particularly preferably from 0.001 to 0.1 wt .-% titanium and a content of free isocyanate groups of at least 0.1 wt .-%, preferably 0.5 to 10 wt .-%, particularly preferably of 1 to 5 wt .-% based on the total composition.
- the titanium contained in the composition according to the invention is present as titanium tetramethanolate, titanium tetraethanolate, titanium tetrapropylate, titanium tetraisopropylate, titanium tetra-n-butylate, titanium tetra-i-butylate, titanium tetraphenylate, titanium oxide acetylacetonate, titanium acetylacetonate or titanium dialcoholate based on diols.
- the titanium is not present as a compound having an amino group-containing ligand.
- the value of w reflects the functionality of the OH-functionalized, preferably terminated, polyolefin.
- the block copolymers are in particular ABA triblock systems.
- block structures of the formula (AB) m are also possible, where m> 1.
- B ' is a polybutadiene radical containing or preferably consisting of the monomer units derived from 1,3-butadiene
- the isocyanate compound is preferably 4,4'-diphenylmethane diisocyanate, 2,4'-diphenylmethane diisocyanate, toluene diisocyanate isomers, isophorone diisocyanate,
- composition according to the invention can, in addition to the reaction product of a block copolymer based on OH-functional polyolefin and cyclic esters as polyol having at least 1, 8, preferably at least two OH groups, and at least one isocyanate compound, other polyols or their reaction products, the by reaction of the further polyols with di- or polyisocyanates, in particular the diisocyanates mentioned above, are obtained.
- further polyols may be included, for example, polyester polyols, polyether polyols and any hydroxyl-functional components, or their reaction products. The choice of these optional polyols is arbitrary per se.
- polyester polyols e.g. liquid or solid, amorphous or (partially) crystalline polyester polyols having molecular weights with a number average between 1000 g / mol and 30000 g / mol, preferably between 2000 g / mol and 10000 g / mol (calculated from the hydroxyl number) are used, wherein linear Polyester polyols are preferably used.
- polyether polyols e.g. Polyether di- or triols are used. Examples of this are e.g. Homo- and copolymers of ethylene glycol, propylene glycol and / or butanediol-1, 4.
- the number average molecular weight of the mixed polyether polyols should preferably be in a range of from 1000 g / mol to 10000 g / mol, preferably from 2000 g / mol to 8000 g / mol.
- hydroxy-functional polyolefins such as hydroxy-functional polybutadienes, hydroxy-functional polyisoprenes, hydroxy-functional polycarbonates or hydroxy-functional polyacrylates.
- compositions according to the invention may contain up to 50% by weight, based on the total composition, of further additives.
- additives may be, for example: non-OH-functionalized polymers, e.g. B. thermoplastic polyurethanes (TPU) and / or polyacrylates and / or ethylene-vinyl acetate copolymers (EVA); Pigments or fillers, eg. Talc, silica, titania, barium sulfate, calcium carbonate, carbon black or colored pigments; Tackifier, like. z. As rosins, hydrocarbon resins, phenolic resins and anti-aging and auxiliary agents.
- non-OH-functionalized polymers e.g. B. thermoplastic polyurethanes (TPU) and / or polyacrylates and / or ethylene-vinyl acetate copolymers (EVA); Pigments or fillers, eg. Talc, silica, titania, barium sulfate, calcium carbonate, carbon black or colored pigments; Tackifier, like. z. As rosins, hydrocarbon resins,
- compositions according to the invention may preferably be one-component or two-component, moisture- or thermally crosslinking polyurethane adhesives.
- the compositions of the invention can be obtained in various ways.
- the compositions according to the invention are preferably obtained by the process according to the invention described below.
- Titanium tetramethanolate, titanium tetraethanolate, titanium tetrapropylate, titanium tetraisopropylate, titanium tetra-n-butylate, titanium tetra-i-butylate, titanium tetraphenylate, titanium oxide acetylacetonate, titanium acetylacetonate or titanium dialcoholate based on diols are used as the titanium-containing compound.
- the titanium is not present as a compound having an amino group-containing ligand.
- the titanium-containing compound is already used in the preparation of the block copolymer, preferably as a catalyst.
- the proportion of titanium in the reaction mixture is preferably from 0.0001 wt .-% to 1 wt .-%, preferably 0.001 to 0.1 wt .-%.
- the preparation of the block copolymers is preferably carried out by ring-opening reaction (or polymerization), preferably at temperatures of 20 to 250 ° C, preferably in a period of 0.1 to 20 hours.
- the ring-opening reaction may preferably be carried out in the melt or in the presence of solvents.
- cyclic esters C3-lactones such as ⁇ -propiolactone, C4-L.act.0ne such as ⁇ -butyrolactone or ⁇ -butyrolactone
- C5-lactones such as 4-hydroxy-3-pentenoic acid gamma-lactone
- Methylene-Y-butyrolactone ⁇ -methylene-Y-butyrolactone
- C6- Lactones such as ⁇ -hexalactone, ⁇ -caprolactone or ⁇ -hexalactone
- other lactones such as 5-butyl-4-methyldihydro-2 (3H) -furanone, ⁇ -octanolactones, ⁇ -pheriyl-e-caprolactone, oxacyclododecan-2-one , Oxacyclotri
- a mixture of ⁇ -caprolactone and lactide is preferably used.
- polybutadiene is preferably a polybutadiene containing or preferably consisting of the monomer units derived from 1,3-butadiene
- (C4H6) n a butadiene oligomer containing or preferably consisting of the repeating units (II), (III) and (IV) and the respective chain ends are OH groups.
- the number average molecular weight, as determined by gel permeation chromatography, of the hydroxy-terminated polybutadienes is preferably from 500 to 10,000 g / mol, preferably from 1, 000 to 5,000 g / mol, and more preferably from 1, 500 to 4,000, g / mol.
- polybutadiene may be in a partially or fully hydrogenated form.
- the hydroxy-terminated polybutadienes used according to the invention are preferably prepared by free-radical polymerization, for example by polymerization of 1,3-butadiene in the presence of hydrogen peroxide, water and an organic solvent. Suitable processes are described, for example, in EP 2 492 292.
- the polybutadienes which can preferably be used in the context of the present invention are commercially available, for example as POLYVEST® HT from Evonik Resource Efficiency GmbH.
- the functionality of the OH-functional, preferably OH-terminated polyolefins used, preferably polybutadienes, which are unhydrogenated, is preferably in the range from 1.8 to 5, preferably in the range from 2 to 3.5, and particularly preferably in the range from 2 to third
- Essential in the context of the present invention is the presence of OH groups to form the copolymers. These OH groups are preferably present at the chain end of the polybutadiene, moreover, further OH groups can be present along the chain in the OH-terminated polybutadienes. In the context of the present invention, the functionality is determined by the correlation of molecular weight to OH.
- isocyanate compound is preferably 4,4'-diphenylmethane diisocyanate, 2,4'-diphenylmethane diisocyanate, toluene diisocyanate isomers, isophorone diisocyanate, hexamethylene diisocyanate, 4,4'-dicyclohexylmethane diisocyanate or mixtures thereof, preferably 4,4'-diphenylmethane diisocyanate or a mixture of 4,4 '- Diphenylmethandiisocyanat and 2,4'-diphenylmethane diisocyanate used.
- compositions according to the invention preferably produces the compositions according to the invention.
- the compositions of the invention further polyols or their reaction products, which are obtained by reacting the other polyols with di- or polyisocyanates, especially those mentioned above, included.
- polyester polyols e.g. Polyester polyols, polyether polyols and any hydroxyl-functional components can be used.
- the choice of these optional polyols is arbitrary per se.
- polyesters e.g. liquid or solid, amorphous or (partially) crystalline polyesters having molecular weights with a number average between 1000 g / mol and 30000 g / mol, preferably between 2000 g / mol and 10000 g / mol (calculated from the hydroxyl number), wherein linear Polyester polyols are preferably used.
- polyether polyols e.g. Polyether di- or triols are used. Examples of this are e.g. Homo- and copolymers of ethylene glycol, propylene glycol and / or butanediol-1, 4.
- the number average molecular weight of the mixed polyether polyols should preferably be in a range of from 1000 g / mol to 10000 g / mol, preferably from 2000 g / mol to 8000 g / mol.
- hydroxy-functional polyolefins such as hydroxy-functional polybutadienes, hydroxy-functional polyisoprenes, hydroxy-functional polyolefins, hydroxy-functional polycarbonates or hydroxy-functional polyacrylates.
- compositions according to the invention are particularly suitable for the production of adhesions of substrates and / or for vibration or Noise attenuation.
- substrates are preferably z.
- plastics metals, woods, mineral substrates such.
- the type and extent of the bond are not limited.
- the substrates are oily substrates.
- Oily substrates are to be understood as those substrates which contain natural, synthetic or mineral oils on the surface.
- the oily substances can reach the substrates by processing steps (eg drawing fats, waxes, release agents, etc.) or get into the substrates or they can reach the surface from the substrate (eg oily wood species such as teak, for example Wood or meranti wood).
- the adhesions are preferably adhesions in the woodworking and furniture industry (for example assembly bonding and the lamination and lamination of decorative films on fiberboard), in the automotive sector (for example lamination of films or textiles on door side parts, roof lining, seat production and retainer bonding, add-on parts in the automotive industry) (semi) -structural area, fiber-reinforced composites and / or metals), in the construction industry, shoe industry and textile industry (for example siliconized or hydrophobized textiles) as well as in window construction (for example for profile wrapping).
- the adhesives of the invention are suitable in the packaging industry, as sealants and as a coating material.
- reaction products of the invention are suitable both for use in one-component and in two-component systems.
- the preparation of the mixture takes place independently of the adhesive application, usually at a much earlier date.
- the curing takes place, for example, by moisture or thermally induced reaction of the reaction partners contained in the adhesive.
- the mixture is prepared immediately before the adhesive is applied.
- compositions of the invention can be applied by any known method, e.g. Extruder, caterpillar, die, brush, Dipping, spraying, pouring, rolling, spraying, printing, wiping, washing, tumbling, centrifuging, powder (electrostatic).
- the number average and the weight average molecular weight of the block copolymers used in the context of the present invention is determined according to DIN 55672-1 by gel permeation chromatography in tetrahydrofuran as the eluent and polystyrene for calibration.
- the polydispersity (U) Mw / Mn.
- the prepared block copolymers have hydroxyl groups as end groups.
- the concentration of the OH groups is determined according to DIN 53240-2 titrimetrically in mgKOH / g polymer.
- the viscosity of the block copolymers prepared and of the reaction products of block copolymer and diisocyanate was determined on the basis of DIN EN ISO 3219 using a rotary viscometer in Pa.s at the respectively indicated temperature.
- the NCO number of the reaction products prepared from block copolymer with diisocyanate was determined by titrimetry in% by weight based on DIN EN 1242.
- DYNACOLL 7360 Hydroxy-terminated polyester from Evonik Resource Efficiency GmbH
- the catalysts used can be taken from Table 1 Table 1: Information on the catalysts used
- Table 2a Amounts of the substances used in Examples 1a-h and 2a-h and results of the test
- Example 1 a Example 1 b
- Example 1 c Example 1 d
- Table 2b Amounts of the substances used in Examples 1a-h and 2a-h and results of the test
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP17199866.9A EP3480231A1 (en) | 2017-11-03 | 2017-11-03 | Reactive adhesives based on block copolymers |
PCT/EP2018/079873 WO2019086538A1 (en) | 2017-11-03 | 2018-10-31 | Reactive adhesives based on block copolymers |
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EP3704173A1 true EP3704173A1 (en) | 2020-09-09 |
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EP17199866.9A Pending EP3480231A1 (en) | 2017-11-03 | 2017-11-03 | Reactive adhesives based on block copolymers |
EP18796040.6A Pending EP3704173A1 (en) | 2017-11-03 | 2018-10-31 | Reactive adhesives based on block copolymers |
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EP17199866.9A Pending EP3480231A1 (en) | 2017-11-03 | 2017-11-03 | Reactive adhesives based on block copolymers |
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US (1) | US11384194B2 (en) |
EP (2) | EP3480231A1 (en) |
TW (1) | TW201922836A (en) |
WO (1) | WO2019086538A1 (en) |
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EP3243863A1 (en) | 2016-05-09 | 2017-11-15 | Evonik Degussa GmbH | Use of block copolymers in adhesives |
CN113024782A (en) * | 2020-12-30 | 2021-06-25 | 苏州福斯特光伏材料有限公司 | Polyester resin for preparing adhesive for aluminum plastic film and preparation method and application thereof |
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US4727099A (en) * | 1986-08-15 | 1988-02-23 | E. I. Du Pont De Nemours And Company | Coating composition containing a reactive urethane component, a hydroxyl containing acrylic polymer having pendent ester groups and a metallic alkylate catalyst |
JPH0627188B2 (en) * | 1986-11-07 | 1994-04-13 | 竹本油脂株式会社 | Modifier for synthetic resin materials |
JP5842315B2 (en) * | 2008-12-01 | 2016-01-13 | 三菱化学株式会社 | Method for producing polyurethane and use of polyurethane obtained therefrom |
CN104334605B (en) | 2012-05-25 | 2016-05-04 | 普立万公司 | The oxygen scavenging copolymers of being made by annular aliphatic monomer |
EP2492292A1 (en) | 2012-05-29 | 2012-08-29 | Evonik Industries AG | Polymerisation of dienes |
KR20170043598A (en) * | 2014-08-18 | 2017-04-21 | 바스프 에스이 | Polyester-modified polybutadienols for producing polyurethane elastomers and thermoplastic polyurethanes |
DE102014217783A1 (en) | 2014-09-05 | 2016-03-10 | Evonik Degussa Gmbh | Two-component polyurethane hotmelt adhesive with high initial and final strength |
WO2016124518A1 (en) | 2015-02-05 | 2016-08-11 | Evonik Degussa Gmbh | Isocyanate-free synthesis of carbonate-modified polymers |
CN107278212B (en) | 2015-03-02 | 2020-03-10 | 赢创德固赛有限公司 | Adhesive with low VOC and fogging value |
WO2016139146A1 (en) | 2015-03-02 | 2016-09-09 | Evonik Degussa Gmbh | Adhesives with low voc and fogging values |
JP6803343B2 (en) | 2015-06-30 | 2020-12-23 | エボニック オペレーションズ ゲーエムベーハー | Isocyanate-free reactive polyurethane composition |
EP3184568A1 (en) | 2015-12-21 | 2017-06-28 | Evonik Degussa GmbH | Acrylate-terminated urethane polybutadienes from low-monomer 1:1 monoadductes from reactive olefinic compounds and diisocyanates and hydroxy-terminated polybutadienes for liquid optically clear adhesives (locas) |
EP3243864A1 (en) | 2016-05-09 | 2017-11-15 | Evonik Degussa GmbH | Use of block copolymers in coatings |
EP3243863A1 (en) | 2016-05-09 | 2017-11-15 | Evonik Degussa GmbH | Use of block copolymers in adhesives |
CA3044616A1 (en) | 2016-12-14 | 2018-06-21 | Evonik Oil Additives Gmbh | Use of polyesters as viscosity index improvers for aircraft hydraulic fluids |
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2017
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- 2018-10-31 EP EP18796040.6A patent/EP3704173A1/en active Pending
- 2018-10-31 WO PCT/EP2018/079873 patent/WO2019086538A1/en unknown
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US20200377641A1 (en) | 2020-12-03 |
TW201922836A (en) | 2019-06-16 |
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