EP1966264A1 - Feuchtigkeitshärtende heissschmelzklebstoffe umfassend mindestens ein silanfunktionelles polyurethanprepolymer - Google Patents
Feuchtigkeitshärtende heissschmelzklebstoffe umfassend mindestens ein silanfunktionelles polyurethanprepolymerInfo
- Publication number
- EP1966264A1 EP1966264A1 EP06830810A EP06830810A EP1966264A1 EP 1966264 A1 EP1966264 A1 EP 1966264A1 EP 06830810 A EP06830810 A EP 06830810A EP 06830810 A EP06830810 A EP 06830810A EP 1966264 A1 EP1966264 A1 EP 1966264A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- moisture
- silane
- melt adhesive
- adhesive composition
- formula
- 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.)
- Withdrawn
Links
- 239000004831 Hot glue Substances 0.000 title claims abstract description 58
- 229920001730 Moisture cure polyurethane Polymers 0.000 title claims abstract description 38
- 238000013008 moisture curing Methods 0.000 title claims abstract description 33
- 239000000203 mixture Substances 0.000 claims abstract description 53
- 238000001723 curing Methods 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 239000012780 transparent material Substances 0.000 claims abstract description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 31
- 229920005862 polyol Polymers 0.000 claims description 26
- 150000003077 polyols Chemical class 0.000 claims description 26
- 239000000758 substrate Substances 0.000 claims description 20
- 229920001228 polyisocyanate Polymers 0.000 claims description 18
- 239000005056 polyisocyanate Substances 0.000 claims description 18
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 17
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 claims description 17
- 150000002009 diols Chemical class 0.000 claims description 15
- 229920000728 polyester Polymers 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 238000004806 packaging method and process Methods 0.000 claims description 6
- 239000011521 glass Substances 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000005442 diisocyanate group Chemical group 0.000 claims description 4
- 229920003023 plastic Polymers 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000004753 textile Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 239000012790 adhesive layer Substances 0.000 claims description 2
- 239000002985 plastic film Substances 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 239000000853 adhesive Substances 0.000 description 22
- 230000001070 adhesive effect Effects 0.000 description 21
- -1 alkali metal alkoxides Chemical class 0.000 description 16
- 229920005906 polyester polyol Polymers 0.000 description 11
- 229920002635 polyurethane Polymers 0.000 description 8
- 239000004814 polyurethane Substances 0.000 description 8
- 238000003860 storage Methods 0.000 description 8
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 7
- 229920000570 polyether Polymers 0.000 description 7
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 7
- 229910000077 silane Inorganic materials 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical class CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- WMRCTEPOPAZMMN-UHFFFAOYSA-N 2-undecylpropanedioic acid Chemical compound CCCCCCCCCCCC(C(O)=O)C(O)=O WMRCTEPOPAZMMN-UHFFFAOYSA-N 0.000 description 3
- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 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
- 238000001816 cooling Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 150000004072 triols Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 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 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 239000003677 Sheet moulding compound Substances 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
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- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 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 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910001092 metal group alloy Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 2
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- 238000009864 tensile test Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
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- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 1
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- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 description 1
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- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical class CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
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- BDLNYQVUTQYAGX-UHFFFAOYSA-N 3-(diethoxymethylsilyl)propane-1-thiol Chemical compound CCOC(OCC)[SiH2]CCCS BDLNYQVUTQYAGX-UHFFFAOYSA-N 0.000 description 1
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- KTJUNCYQALUJRL-UHFFFAOYSA-N dimethoxymethylsilylmethanethiol Chemical compound COC(OC)[SiH2]CS KTJUNCYQALUJRL-UHFFFAOYSA-N 0.000 description 1
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- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 230000006855 networking Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical class CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005903 polyol mixture Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000005488 sandblasting Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- QJOOZNCPHALTKK-UHFFFAOYSA-N trimethoxysilylmethanethiol Chemical compound CO[Si](CS)(OC)OC QJOOZNCPHALTKK-UHFFFAOYSA-N 0.000 description 1
- GRXOWOKLKIZFNP-UHFFFAOYSA-N undecane-1,1-diol Chemical class CCCCCCCCCCC(O)O GRXOWOKLKIZFNP-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002025 wood fiber Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
-
- 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
- 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
- C08G2170/00—Compositions for adhesives
- C08G2170/20—Compositions for hot melt adhesives
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31598—Next to silicon-containing [silicone, cement, etc.] layer
- Y10T428/31601—Quartz or glass
-
- 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.]
- Y10T428/31609—Particulate metal or metal compound-containing
- Y10T428/31612—As silicone, silane or siloxane
-
- 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]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
Definitions
- Hotmelt adhesives are known adhesives. Such adhesives are solid at room temperature and solvent-free adhesives, which are melted for application and applied as a melt on the substrate to be bonded. In contrast to the so-called
- Hot melt adhesives which pasty adhesives represent and be applied at slightly elevated temperatures up to typically 60 0 C, the application of the hot melt adhesives takes place at temperatures from 85 ° C. Due to the cooling, the adhesives solidify.
- Such reactive polyurethane hotmelt adhesives are known, for example from EP-A-0 244 608 or US Pat. No. 5,155,180 or EP-A-1 036 103, and are used widely commercially.
- a disadvantage of the moisture-curing hot melt adhesives having isocyanate groups is that they often lead to excessive blistering, in particular with increased humidity and / or temperature.
- blisters are usually undesirable, especially when it comes to visible bonds, as they often occur, for example, in packaging applications.
- Silane-functional polyurethanes have long been used as moisture-curing adhesives and sealants. These silane-functional polyurethanes contain silane groups as reactive groups and are typically prepared by the reaction of isocyanate-group-containing polyurethane prepolymers with aminosilanes.
- polyurethane adhesives produced in this way have the great disadvantage that the viscosity of the adhesive can increase sharply with prolonged heating.
- EP-A-0 202 491 mentions silane-functionalized polyester hotmelt adhesives in which an adduct of a polyester polyol and a diisocyanate is reacted with an amino- or mercaptosilane or an adduct of an amino- or mercaptosilane and a diisocyanate is reacted with a polyester polyol.
- EP-A-0 371 370 discloses moisture-curing postcrosslinking hotmelt adhesives which have terminal alkoxysilane and / or NCO groups. Furthermore, EP-A-0 371 370 discloses that these alkoxysilane end groups can be introduced via mercaptosilane or via a series of aminosilanes. Neither EP-A-0 371 370 nor EP-A-0 202 491 differentiate between aminosilanes and mercaptosilanes for functionalizing the polymer.
- the object of the present invention is, therefore, moisture-curing
- compositions cure without bubbles and surprisingly have a very good durability even at high temperatures (viscosity stability).
- Isocyanate group-containing polyurethane prepolymers can be obtained, which the durability (viscosity stability) of the hotmelt adhesives can be greatly improved at high temperatures. Furthermore, it has been found that the use of silane-functional polyurethane prepolymers of the formula (I) in hot-melt adhesives for improving the durability
- the invention relates to moisture-curing hot-melt adhesive compositions comprising at least one silane-functional polyurethane prepolymer of the formula (I)
- R 1 is an n-valent organic radical of a prepolymer P which is prepared from at least one polyol and at least one polyisocyanate and has at least n isocyanate groups, after removal of n isocyanate groups;
- R 2 is an alkyl group having 1 to 10 C atoms
- R 3 is a linear or branched alkylene group having 1 to 10 C atoms
- X is a hydrolyzable radical; a is a value of 0, 1 or 2; n is a value of 2 or more, and wherein the prepolymer P is solid at room temperature and has no further silane group.
- Polyisocyanate indicates in this document that the respective substance formally contains more than one of the functional group occurring in its name per molecule.
- silane group refers to a group bonded to an organic radical via a silicon atom, which is hydrolyzable, that is, having from one to three hydrolyzable radicals -OH groups) and, by subsequent condensation reactions of the silanol groups, siloxane groups (Si-O-Si groups).
- silane refers to low molecular weight organic compounds which carry at least one silane group.
- silane-functional denotes compounds, in particular polymers, which have silane groups.
- Hydrolyzable radical is understood as meaning those radicals on a silane group which are displaced integrally from the silicon atom by water in a hydrolysis reaction and are formally replaced there by a hydroxyl group In the hydrolysis reaction, the hydrolyzable group is protonated to a low molecular weight compound which may be organic or inorganic.
- hydrolyzable radicals X in the silane-functional polyurethane prepolymer of the formula (I) are, above all, those which are customary in silicone chemistry, in particular those which are selected from the group consisting of the formula (X-1), (X-2) , (X-3), (X-4), (X-5), (X-6), (X-7) and (X-8).
- R 'and R "independently of one another are alkyl or aryl and R 4 is an alkyl group having 1 to 10 C atoms, which optionally contains 1 or 2 ether oxygens, in particular an alkyl group having 1 to 4 C atoms Particularly preferably, the hydrolyzable radical X is an alkoxy group -OR 4 .
- two alkoxy groups -OR 4 together represent an alkylenedioxy group -OR 5 O- which form a five- or six-membered ring with the silicon atom, R 5 being an alkylene group having 2 to 10, especially 2 or 3 , C-atoms stands.
- R 5 being an alkylene group having 2 to 10, especially 2 or 3 , C-atoms stands.
- the prepolymer P has no further silane group.
- Silane designations with functional groups as prefixes, such as "aminosilane” or "mercaptosilane” denote silanes which carry the said functional group on the organic radical as a substituent.
- R 3 is propylene
- hydrolyzable radical X the radicals -OMethyl, -Oethyl or -O-isoPropyl, in particular -OMethyl, are preferred.
- the prepolymer P is prepared from at least one polyol and at least one polyisocyanate.
- Preferred polyols are polyether polyols, polyester polyols and polycarbonate polyols.
- polyether polyols also called polyoxyalkylene polyols
- polyoxyalkylene polyols are those which are polymerization products of ethylene oxide, 1,2-propylene oxide, 1,2- or 2,3-butylene oxide, tetrahydrofuran or mixtures thereof, possibly polymerized with the aid of a starter molecule having two or more active hydrogen atoms such as water, ammonia or compounds having several OH or NH groups such as 1, 2-ethanediol, 1, 2- and 1, 3-propanediol, neopentyl glycol, diethylene glycol, triethylene glycol, the isomeric dipropylene glycols and tripropylene glycols, the isomers Butanediols, pentanediols, hexanediols, heptanediols, octanediols, nonanediols, decanediols, undecane
- Both polyoxyalkylene polyols having a low degree of unsaturation can be used Grams of polyol (mEq / g)) prepared, for example, by means of so-called double metal cyanide complex catalysts (DMC catalysts), as well as polyoxyalkylene polyols having a higher degree of unsaturation, prepared for example with the aid of anionic catalysts such as NaOH, KOH or alkali metal alkoxides.
- DMC catalysts double metal cyanide complex catalysts
- polyether polyols are polyoxyalkylene diols or polyoxyalkylene triols, in particular polyoxyethylene diols or polyoxyethylene triols.
- polyoxyalkylenediols or polyoxyalkylenetriols having a degree of unsaturation lower than 0.02 meq / g and having a molecular weight in the range from 1000 to 30,000 g / mol, and also polyoxypropylenediols and -triols having a molecular weight of from 400 to 8,000 g / mol ,
- EO-endcapped ethylene oxide-endcapped polyoxypropylene diols or triols
- polyoxypropylene diols or triols being specific polyoxypropylene polyoxyethylene polyols obtained, for example, by alkoxylating pure polyoxypropylene polyols with ethylene oxide after completion of the polypropoxylation and thereby having primary hydroxyl groups
- molecular weight or “molar weight” is always understood to mean the molecular weight average M n .
- Diols having a molecular weight which are generally suitable are polyether polyols
- such polyethers are sold under the trade name Acclaim® by Bayer.
- Suitable polyester polyols are in particular those which are prepared from dihydric to trivalent, preferably dihydric, alcohols, for example 1,2-ethanediol, diethylene glycol, 1,2-propanediol, dipropylene glycol, 1,4-butanediol, 1,5 -Pentanediol, 1, 6-hexanediol, neopentyl glycol, glycerol, 1, 1, 1-thmethylolpropane or mixtures of the aforementioned alcohols, with organic dicarboxylic acids or their anhydrides or esters such as succinic acid, glutaric acid, adipic acid, suberic acid, sebacic acid, dodecanedicarboxylic acid, maleic acid , Fumaric acid, phthalic acid, isophthalic acid, terephthalic acid and hexahydrophthalic acid or mixtures of the aforementioned acids, as well as polyester polyols from lactones such as ⁇
- polyester polyols are polyester polyols of adipic acid, sebacic acid or dodecanedicarboxylic acid as the dicarboxylic acid and of hexanediol or neopentyl glycol as the dihydric alcohol.
- the polyester polyols preferably have a molecular weight of 1500 to 15O00 g / mol, in particular from 1500 to 8000 g / mol, preferably from 2000 to 5500 g / mol.
- Particularly suitable crystalline or partially crystalline polyester polyols are adipic acid / hexanediol polyester and dodecanedicarboxylic acid / hexanediol polyester.
- Suitable polycarbonate polyols are those which are obtainable by reacting, for example, the abovementioned alcohols used to form the polyesterpolyols with dialkyl carbonates, diaryl carbonates or phosgene.
- Preferred polyols are diols, especially polyether diols, polyester diols and polycarbonate diols.
- polyester diols in particular a mixture of an amorphous and a crystalline or partially crystalline polyester diol.
- a polyisocyanate contains two or more NCO groups and describes in the present document in each case a low molecular weight compound having a molecular weight of less than 1000 g / mol.
- polyisocyanates examples include aromatic polyisocyanates, such as 2,4- and 2,6-toluene diisocyanate (TDI) and any mixtures of these isomers, 4,4'-, 2,4'- and 2,2'-diphenylmethane diisocyanate and any Mixtures of these isomers (MDI), mixtures of MDI and MDI homologs (polymeric MDI or PMDI), 1, 3 and 1, 4-phenylene diisocyanate, naphthalene-1, 5-diisocyanate (NDI), 3,3'-dimethyl 4,4'-diisocyanatodiphenyl (TODI), Oligomers and polymers of the aforementioned isocyanates, as well as any mixtures of the aforementioned isocyanates.
- aromatic polyisocyanates are MDI and TDI.
- polyisocyanates are aliphatic and cycloaliphatic polyisocyanates, such as 1,6-hexamethylene diisocyanate (HDI), 2-methylpentamethylene-1,5-diisocyanate, 2,2,4- and 2,4,4-trimethyl-1,6.
- HDI 1,6-hexamethylene diisocyanate
- 2-methylpentamethylene-1,5-diisocyanate 2,2,4- and 2,4,4-trimethyl-1,6.
- hexamethylene diisocyanate TMDI
- 1,1-dodecamethylene diisocyanate cyclohexane-1, 3- and 1,4-diisocyanate and any desired mixtures of these isomers
- IPDI isophorone diisocyanate or IPDI
- HMDI 1,4-diisocyanato-2,2,6-trimethylcyclohexane
- TMCDI m- and p-xylylene diisocyanate
- m- and p-XDI m- and p-tetramethyl-1, 3- and -1
- 4-xylylene diisocyanate m- and p-TMXDI).
- the polyisocyanate is a diisocyanate having a molecular weight of less than 400 g / mol.
- the preparation of the prepolymer P takes place in a known manner and
- the prepolymers P have free isocyanate groups and are solid at room temperature.
- the number of isocyanate groups is very dependent on the desired end properties of the cured adhesive.
- the polyurethane prepolymer is prepared via a reaction of at least one polyisocyanate and at least one polyol, preferably an amorphous and a crystalline polyester polyol, with a stoichiometric excess of isocyanate groups.
- the prepolymer P has a molecular weight of preferably more than 2000 g / mol, in particular such between 2000 and 50,000 g / mol, preferably one between 4000 and 30,000 g / mol.
- the prepolymer P n has isocyanate groups. Depending on the functionality of the polyols and polyisocyanates used, n assumes a value of 2 or higher. It is advantageous if n has a value of 2 to 4. In a preferred embodiment, n is 2. It is clear to the person skilled in the art that the polyols and polyisocyanates used are usually mixtures with different functionalities.
- a technical "diol” actually contains not only the diol but also monols, so that the average functionality is not 2 but less than 2.
- technical "diols” can also deplete additions of triplets, so that the middle Functionality is not 2 but more than 2.
- the preparation of the silane-functional polyurethane prepolymer of the formula (I) is preferably carried out by the reaction of a prepolymer P, as just described, with a mercaptosilane of the formula (II)
- Suitable mercaptosilanes are, for example, mercaptomethyltrimethoxysilane, mercaptomethylethethoxysilane, mercaptomethyldimethoxymethylsilane, mercaptomethyldiethoxymethylsilane, 3-mercaptopropyltrimethoxysilane, 3-mercaptopropyltriethoxysilane, 3-mercaptopropyltriisopropoxysilane, 3-mercaptopropyl- methoxy (1, 2-ethylenedioxy) silane, 3-mercaptopropylmethoxy (1,2-propylenedioxy) silane, 3-mercaptopropylethoxy (1,2-propylenedioxy) silane, 3-mercaptopropyldimethoxymethylsilane, 3-mercaptopropyl -diethoxymethylsilane, 3-mercapto-2-methylpropyl-trimethoxysilane, 4-mercapto-3,3-dimethylbutyl-thmethoxysi
- Suitable mercaptosilanes are 3-mercaptopropyltrimethoxysilane and 3-mercaptopropyltriethoxysilane, in particular 3-mercaptopropyltrimethoxysilane.
- the reaction of the isocyanate group-containing prepolymer P with the mercaptosilane is carried out in a known manner.
- the mercaptosilane is used stoichiometrically or superstoichiometrically and a silane-functional polyurethane prepolymer of the formula (I) is obtained which has no isocyanate groups, that is to say that all n isocyanate groups of the prepolymer P have reacted.
- the mercaptosilane is used substoichiometrically and there is a silane-functional polyurethane prepolymer of the formula (I) which, in addition to the silane groups, still has isocyanate groups, that is to say that not all n isocyanate groups of the prepolymer P have reacted.
- silane-functional polyurethane prepolymer of formula (I) still has isocyanate groups.
- silane-functional polyurethane prepolymer of the formula (I) has no isocyanate groups.
- the silane-functional polyurethane prepolymer of the formula (I) preferably has no isocyanate groups.
- the moisture-curing hot-melt adhesive composition may contain further additives such as plasticizers, fillers, adhesion promoters, UV absorbers, UV or heat stabilizers, antioxidants, flame retardants, optical brighteners, catalysts, color pigments or dyes.
- plasticizers such as plasticizers, fillers, adhesion promoters, UV absorbers, UV or heat stabilizers, antioxidants, flame retardants, optical brighteners, catalysts, color pigments or dyes.
- Particularly suitable catalysts are those which catalyze the hydrolysis and / or crosslinking of silane groups.
- Such catalysts include, for example, titanates, organotin compounds such as di-butyltin dilaurate and dibutyltin diacetylacetonate, bismuth organic compounds or bismuth complexes, amino-containing compounds, for example 1,4-diazabicyclo [2.2.2] octane or 2,2'-dimorpholinodiethyl ether.
- the hotmelt adhesive composition is free of carbon black. Soot, especially in the polyurethane Chemistry, especially in conventional one-component polyurethane adhesives or one-component polyurethane hot melt, often added as a filler to improve the mechanics of the adhesive, as well as to make the low-viscosity adhesives stable.
- the adhesive is free of inorganic fillers.
- carbon black filled adhesives are poorly suited for those applications in which the aesthetics of the bonds are considered important, and where at least one of the substrates to be bonded is transparent or translucent.
- a soot-free, or a hot melt adhesive composition which is free of inorganic fillers such applications are possible without the mechanics or application being adversely affected.
- the adhesive is meltable, ie that it has a sufficiently low viscosity at the application temperature that allows a sensible application, and that it quickly solidifies on cooling, so that it quickly Can absorb forces even before the crosslinking reaction is complete with humidity. It has been found that the moisture Heissschmelzklebstoffzusammenset- wetting at a temperature of 150 0 C and in particular a viscosity of less than 100'0OO mPas, in particular of less than 50'0OO mPas and at 70 0 C in particular a viscosity of greater than 20'000 mPas, in particular of more than 50'0OO mPas.
- silane-functional polyurethane prepolymer of the formula (I) can also be mixed with other polyurethane prepolymers, whereby the stability (viscosity stability) at elevated temperature of the moisture-curing hot-melt adhesive thus formed can be improved.
- the invention comprises a method for bonding substrate S1 to substrate S2.
- This method comprises the steps of i) heating a moisture-curing hot-melt adhesive composition, as described above, to a
- step iii) typically closes
- Step iv) of chemical curing of the moisture-curing hot melt adhesive composition with atmospheric moisture The person skilled in the art understands that, depending on the system used, temperature and reactivity of the adhesive, crosslinking reactions, and thus chemical curing, can already begin during the application. However, the bulk of networking, and thus in the narrow sense of the term chemical curing, takes place after application.
- the substrates S1 and / or S2 can be pretreated before applying the hot-melt adhesive composition.
- Pretreatments include in particular physical and / or chemical
- the substrates S1 and S2 may be a variety of materials.
- plastics organic materials such as leather, fabrics,
- Paper, wood, resin-bonded wood materials, resin-texil composites Fabrics, glass, porcelain, ceramics and metals and metal alloys, in particular painted or powder-coated metals and metal alloys.
- plastics are polyvinyl chloride (PVC), acrylonitrile-butadiene-styrene copolymers (ABS), SMC (sheet molding composites), polycarbonate (PC), polyamide (PA), polyester (PE), polyoxymethylene (POM), Polyolefins (PO), in particular polyethylene (PE) or polypropylene (PP), preferably with plasma, corona or flame-treated PP or PE.
- PVC polyvinyl chloride
- ABS acrylonitrile-butadiene-styrene copolymers
- SMC sheet molding composites
- PC polycarbonate
- PA polyamide
- PET polyester
- POM polyoxymethylene
- PO Polyolefins
- PE polyethylene
- PP polypropylene
- the substrates S1 and S2 are transparent materials, in particular transparent plastic films.
- Another preferred transparent material is glass, especially in the form of a disk.
- the moisture-curing hot-melt adhesive composition is used in particular in an industrial manufacturing process.
- the moisture-curing hot-melt adhesive composition is suitable for bonds in which the bonding site is visible.
- it is particularly suitable for the bonding of glass, in particular in vehicle and window construction.
- it is particularly suitable for the gluing of transparent packaging.
- the adhesive cures substantially free of bubbles.
- Typical thicknesses of bonds are 10 microns or more.
- the bond thickness is between 10 microns and 1000 microns, especially between 80 microns and 500 microns. It has been shown that even in bonding layer thicknesses of over 80 microns no bubbles occur.
- articles are in particular articles of the transport, furniture or textile industry.
- the automotive industry in particular is preferred.
- Exemplary such articles are automotive interior trim parts such as headliner, sun visor, instrument panel, door side panel, parcel shelf and the same; Wood fiber materials from the shower and bath area; Furniture decorative films, membrane films with textiles such as cotton, polyester films in the clothing sector or textiles with foams for automotive equipment.
- such articles are in particular articles from the packaging industry.
- such an article is a transparent packaging.
- Another aspect of the present invention is the use of mercaptosilanes of formula (II) already described for modifying isocyanate group-containing polyurethane prepolymers to improve the durability (viscosity stability) of a silane-functional uncured
- radicals have the meanings and preferences already described for formula (I).
- Preferred mercaptosilanes are 3-mercaptopropyltrimethoxysilane and 3-mercaptopropyltriethoxysilane, in particular 3-mercaptopropyltrimethoxysilane.
- silane-functional polyurethane prepolymers can be obtained from isocyanate-group-containing polyurethane urethane prepolymers which can greatly improve the stability (viscosity stability) of the hotmelt adhesives at high temperatures, in particular in comparison with the corresponding silane-functional polyurethane prepolymers be obtained from isocyanate group-containing polyurethane prepolymers and aminosilanes. Furthermore, it has been found that the use of silane-functional polyurethane prepolymers of the formula (I) in hot-melt adhesives leads to an improvement in the stability (viscosity stability) of moisture-curing hot-melt adhesives at high temperatures.
- Another aspect of the present invention is the use of a silane-functional polyurethane prepolymer of the formula (I) as it already is in hot-melt adhesives for improving the durability (viscosity stability) of the uncured adhesive.
- a hotmelt adhesive based on silane-functional polyurethane prepolymers of the formula (I) has a significantly better viscosity stability at elevated temperature than a corresponding prior art adhesive which is based on silane-functional polyurethane prepolymers consisting of isocyanate groups. containing polyurethane prepolymers and aminosilanes.
- the phenomenon that the increase in viscosity with the storage time at high temperature, which corresponds in particular to the application temperature, ie typically at a storage temperature between 120 0 C and 160 0 C, not or only very much weaker or slower increases, is in this document term "durability" or "viscosity stability".
- Viscosity stabilization found that the UV stability, in particular the yellowing of the moisture-curing hot melt adhesive compositions by the use of cycloaliphatic polyisocyanates in the preparation of the prepolymer P, or the silane-functional polyurethane prepolymer of the formula (I) could be greatly reduced.
- a 1: 1 (w: w) polyester blend of Dynacoll® 7150 (Degussa) and Dynacoll® 7250 (Degussa) was charged in a 1 liter reaction vessel with non-stick coating and a 4-neck flat ground cover. This was melted in an oil bath with temperature control at 120-125 0 C for 4 hours.
- the prepolymer P1 thus prepared had an NCO content of 2.2% and a viscosity of 15,500 mPas at 130 0 C.
- the prepolymer P2 was prepared in an analogous manner as P1, except that for P2, the polyester mixture was stoichiometrically replaced by the polyether polyol Desmophen® 4028 BD (Bayer).
- the prepolymer P2 prepared in this way had an NCO content of 2.05% and a viscosity of 1875 mPas (10 rpm) at 70 ° C.
- prepolymer P1 was treated with the corresponding stoichiometric (1 silane reacted with 1 NCO group) silane used according to Table 2 and 0.2 wt .-% dibutyltin dilaurate (DBTL) as catalyst, based on the prepolymer, and after 1 h reaction time in tubes or cartridges filled. This ensured storage in the absence of moisture.
- DBTL dibutyltin dilaurate
- the viscosity measurement was carried out continuously at the respective temperature.
- the viscosity ⁇ [mPas] of the respective composition was measured by means of Rheomat (Brookfield, Thermosel, spindle 27, shear rate 1 min -1 ) after a storage time t L at the respective temperature T.
- Table 5 Long-term viscosity stability of composition 1 at a storage temperature of 160 ° C.
- Tables 3 to 5 show that the compositions 1 and 2 are distinguished from the reference examples by an extraordinarily improved storage stability. Even at 160 ° C, the viscosity increase is low even after a long storage time, while the reference examples are already so thick thickened that they are no longer measurable.
- specimens were prepared in accordance with the preparation of the specimens for the determination of the Shore A hardness.
- the hot adhesive was in this case filled with a temperature of about 140 0 C in a teflon ring (2mm thickness).
- the glue was pressed with a weight (5kg) on the starch and cooled.
- the cooled adhesive was then demolded and cured at 20 0 C and 55% humidity. Blistering was by visual assessment.
- the prepolymer P1 was used as reference for a reactive hot-melt adhesive.
- composition 1 Tensile shear strength The tensile shear strength of composition 1 was measured on the basis of DIN EN 1465 on a tensile testing machine from Zwick (Z 020) at a test speed of 100 mm / min. Two specimens of the respective substrate were bonded (overlap 12 ⁇ 25 mm, adhesive layer thickness 2 mm) and tested. The mechanical results of composition 1 are in
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- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
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- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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EP06830810A EP1966264A1 (de) | 2005-12-23 | 2006-12-22 | Feuchtigkeitshärtende heissschmelzklebstoffe umfassend mindestens ein silanfunktionelles polyurethanprepolymer |
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EP20050112960 EP1801138A1 (de) | 2005-12-23 | 2005-12-23 | Feuchtigkeitshärtende Heissschmelzklebstoffe umfassend mindestens ein silanfunktionelles Polyurethanprepolymer |
EP06830810A EP1966264A1 (de) | 2005-12-23 | 2006-12-22 | Feuchtigkeitshärtende heissschmelzklebstoffe umfassend mindestens ein silanfunktionelles polyurethanprepolymer |
PCT/EP2006/070161 WO2007074143A1 (de) | 2005-12-23 | 2006-12-22 | Feuchtigkeitshärtende heissschmelzklebstoffe umfassend mindestens ein silanfunktionelles polyurethanprepolymer |
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EP1966264A1 true EP1966264A1 (de) | 2008-09-10 |
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EP20050112960 Withdrawn EP1801138A1 (de) | 2005-12-23 | 2005-12-23 | Feuchtigkeitshärtende Heissschmelzklebstoffe umfassend mindestens ein silanfunktionelles Polyurethanprepolymer |
EP06830810A Withdrawn EP1966264A1 (de) | 2005-12-23 | 2006-12-22 | Feuchtigkeitshärtende heissschmelzklebstoffe umfassend mindestens ein silanfunktionelles polyurethanprepolymer |
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EP20050112960 Withdrawn EP1801138A1 (de) | 2005-12-23 | 2005-12-23 | Feuchtigkeitshärtende Heissschmelzklebstoffe umfassend mindestens ein silanfunktionelles Polyurethanprepolymer |
Country Status (9)
Country | Link |
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US (1) | US8263226B2 (de) |
EP (2) | EP1801138A1 (de) |
JP (1) | JP5254804B2 (de) |
KR (1) | KR101352257B1 (de) |
CN (1) | CN101437861B (de) |
BR (1) | BRPI0620429A2 (de) |
CA (1) | CA2634837A1 (de) |
RU (1) | RU2482136C2 (de) |
WO (1) | WO2007074143A1 (de) |
Families Citing this family (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2031001A1 (de) * | 2007-08-31 | 2009-03-04 | Sika Technology AG | Verwendung einer Heissschmelzklebstoffzusammensetzung als Primer |
US8153268B1 (en) * | 2008-03-26 | 2012-04-10 | Loctite (R&D) Limited | Polymer to metal bonding and compounds and compositions useful therefor |
BRPI0920269A2 (pt) * | 2008-10-17 | 2016-02-10 | Basf Se | proceso para revestimento, para ligação adesiva ou para aglutinação de superfícies de materiais minerais com uma resina plástica. |
EP2189484B1 (de) * | 2008-10-31 | 2011-05-18 | Sika Technology AG | Organomethoxysilan enthaltende Polyurethanzusammensetzung mit anisotropen Materialeigenschaften |
ES2358719T3 (es) * | 2008-10-31 | 2011-05-13 | Sika Technology Ag | Composición de poliuretano que contiene alfa-silano con propiedades de material anisótropas. |
EP2267052A1 (de) * | 2009-05-27 | 2010-12-29 | Sika Technology AG | Feuchtigkeitshärtende Zusammensetzung mit verbesserter Anfangsfestigkeit |
EP2267051A1 (de) * | 2009-05-27 | 2010-12-29 | Sika Technology AG | Silanfunktionelle Polyester in feuchtigkeitshärtenden Zusammensetzungen auf Basis silanfunktioneller Polymere |
JP5533463B2 (ja) * | 2010-09-03 | 2014-06-25 | 横浜ゴム株式会社 | 自動車灯具用一液型湿気硬化性接着剤及びこれを用いる自動車灯具 |
JP5991789B2 (ja) | 2011-11-14 | 2016-09-14 | エルジー・ケム・リミテッド | 接着フィルム |
CN102492389A (zh) * | 2011-12-15 | 2012-06-13 | 广州市白云化工实业有限公司 | 一种湿固化硅烷改性聚氨酯热熔胶组合物及其制备方法 |
EP2664637A1 (de) * | 2012-05-15 | 2013-11-20 | Sika Technology AG | Reaktive Polyurethan-Heissschmelzklebstoffe mit niedrigem Isocyanat-Monomergehalt |
JP5679352B2 (ja) * | 2012-05-23 | 2015-03-04 | モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 | 室温硬化性ケイ素基含有ポリマー組成物 |
ES2733959T3 (es) * | 2012-09-04 | 2019-12-03 | Covestro Deutschland Ag | Aglutinantes con funcionalidad silano con estructura de tiouretano |
WO2014037279A1 (de) * | 2012-09-04 | 2014-03-13 | Bayer Materialscience Ag | Isocyanatosilane mit thiourethanstruktur |
US9982173B2 (en) | 2014-03-11 | 2018-05-29 | Sika Technology Ag | Polyurethane hot-melt adhesive having a low content of diisocyanate monomers and good cross-linking speed |
US20160326408A1 (en) * | 2015-05-08 | 2016-11-10 | Henkel lP & Holding GmbH | Moisture curable hot melt adhesive with high adhesion strength and fast set time |
EP3601466A4 (de) * | 2017-03-30 | 2020-11-25 | Dow Global Technologies LLC | Feuchtigkeitshärtbare polyurethan-heisschmelzharzzusammensetzung |
CN109439266A (zh) * | 2018-08-20 | 2019-03-08 | 苏州市湘园特种精细化工有限公司 | 一种硅烷偶联剂改性无泡单组分聚氨酯胶黏剂的制备方法 |
WO2020092938A1 (en) * | 2018-11-02 | 2020-05-07 | H.B. Fuller Company | Moisture curable hot melt sealant composition |
CN111040715A (zh) * | 2019-12-24 | 2020-04-21 | 烟台德邦科技有限公司 | 一种单组分反应型聚氨酯热熔胶及其制备方法 |
DE102020111278A1 (de) | 2020-04-24 | 2021-10-28 | Klebchemie M.G. Becker Gmbh & Co. Kg | Reaktive Heißschmelzklebstoffzusammensetzungen basierend auf alpha-Silan-terminierten organischen Polymeren |
WO2021230095A1 (ja) * | 2020-05-12 | 2021-11-18 | セメダイン株式会社 | 湿気硬化型ホットメルト接着剤 |
CN112322249B (zh) * | 2020-11-11 | 2022-04-01 | 温州华特热熔胶股份有限公司 | 一种聚酯酰胺硅烷增强热熔胶及其制备方法 |
DE102021127517A1 (de) | 2021-10-22 | 2023-04-27 | Klebchemie M.G. Becker GmbH & Co KG | Reaktive Heißschmelzklebstoffzusammensetzungen basierend auf alpha-Silan-terminierten organischen Polymeren |
Family Cites Families (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3220865C2 (de) * | 1982-06-03 | 1984-08-02 | Dynamit Nobel Ag, 5210 Troisdorf | Haftkleber auf der Basis von hydroxylgruppenhaltigen Polymermischungen |
DE3518357A1 (de) | 1985-05-22 | 1986-11-27 | Dynamit Nobel Ag, 5210 Troisdorf | Feuchtigkeitshaertendes polyestergemisch |
CH666899A5 (de) | 1986-05-09 | 1988-08-31 | Sika Ag | Reaktiver schmelzklebstoff. |
US5250607A (en) * | 1988-01-05 | 1993-10-05 | Norton Company | Moisture cured elastomeric interpenetrating network sealants |
CA1336461C (en) * | 1988-01-05 | 1995-07-25 | Ahmet Comert | Moisture curable hot melt elastomers |
DE3827464A1 (de) * | 1988-08-12 | 1990-02-22 | Henkel Kgaa | Alkoxysilanterminierte, feuchtigkeitsvernetzende schmelzkleber sowie ihre verwendung als klebe- und dichtmassen |
DE3840220A1 (de) | 1988-11-29 | 1990-05-31 | Henkel Kgaa | Verfahren zur herstellung und applikation von unter feuchtigkeitseinwirkung nachvernetzenden schmelzkleber- und/oder dichtmassen |
JPH0735503B2 (ja) | 1989-07-27 | 1995-04-19 | サンスター技研株式会社 | 湿気硬化性熱溶融型接着剤 |
JP3066053B2 (ja) * | 1990-10-05 | 2000-07-17 | サンスター技研株式会社 | 反応性ホットメルト型接着剤 |
JPH09123331A (ja) * | 1995-11-06 | 1997-05-13 | Sekisui Chem Co Ltd | 湿気硬化型接着剤を用いた積層体の製造方法 |
JP3317353B2 (ja) * | 1997-06-17 | 2002-08-26 | コニシ株式会社 | ウレタン系樹脂の製造方法及びウレタン系樹脂組成物 |
ATE223932T1 (de) | 1997-12-01 | 2002-09-15 | Henkel Kgaa | Modifizierter heissschmelzpolyurethanklebstoff |
ATE394437T1 (de) * | 1998-12-11 | 2008-05-15 | Henkel Kgaa | Verwendung von dispersionen silylterminierter polymerer als dichtmassen |
DE10122437A1 (de) * | 2001-05-09 | 2002-11-28 | Henkel Kgaa | Schmelzklebstoff in Form eines Granulates |
DE10150722A1 (de) * | 2001-10-13 | 2003-04-30 | Henkel Kgaa | Reaktive Polyurethan-Zusammensetzungen mit niedrigem Restmonomergehalt |
DE10162642A1 (de) * | 2001-12-20 | 2003-07-10 | Henkel Kgaa | Haftvermittler für reaktive Polyurethane |
US6749943B1 (en) | 2002-07-02 | 2004-06-15 | 3M Innovative Properties Company | Silane based moisture curing hot-melt adhesives |
TW200407390A (en) * | 2002-09-03 | 2004-05-16 | Rohm & Haas | Reactive hot-melt adhesive compositions with improved adhesion to difficult substrates |
JP2004292622A (ja) * | 2003-03-26 | 2004-10-21 | Sekisui Chem Co Ltd | 硬化性組成物、シーリング材及び接着剤 |
US7482420B2 (en) | 2004-03-24 | 2009-01-27 | Construction Research & Technology Gmbh | Silane-terminated polyurethanes with high strength and high elongation |
JP4690329B2 (ja) * | 2004-08-11 | 2011-06-01 | コニシ株式会社 | 反応性ホットメルト樹脂組成物及び反応性ホットメルト接着剤 |
DE102004055450A1 (de) * | 2004-11-17 | 2006-05-18 | Degussa Ag | Feuchtigkeitshärtendes Bindemittel |
-
2005
- 2005-12-23 EP EP20050112960 patent/EP1801138A1/de not_active Withdrawn
-
2006
- 2006-12-22 RU RU2008130407/04A patent/RU2482136C2/ru not_active IP Right Cessation
- 2006-12-22 WO PCT/EP2006/070161 patent/WO2007074143A1/de active Application Filing
- 2006-12-22 JP JP2008546483A patent/JP5254804B2/ja not_active Expired - Fee Related
- 2006-12-22 CN CN2006800525766A patent/CN101437861B/zh not_active Expired - Fee Related
- 2006-12-22 CA CA 2634837 patent/CA2634837A1/en not_active Abandoned
- 2006-12-22 KR KR1020087018102A patent/KR101352257B1/ko not_active IP Right Cessation
- 2006-12-22 EP EP06830810A patent/EP1966264A1/de not_active Withdrawn
- 2006-12-22 BR BRPI0620429-5A patent/BRPI0620429A2/pt not_active IP Right Cessation
- 2006-12-22 US US12/086,748 patent/US8263226B2/en not_active Expired - Fee Related
Non-Patent Citations (1)
Title |
---|
See references of WO2007074143A1 * |
Also Published As
Publication number | Publication date |
---|---|
US8263226B2 (en) | 2012-09-11 |
KR20080081985A (ko) | 2008-09-10 |
CN101437861A (zh) | 2009-05-20 |
JP2009533486A (ja) | 2009-09-17 |
WO2007074143A1 (de) | 2007-07-05 |
CN101437861B (zh) | 2011-12-14 |
JP5254804B2 (ja) | 2013-08-07 |
KR101352257B1 (ko) | 2014-02-17 |
BRPI0620429A2 (pt) | 2011-11-08 |
EP1801138A1 (de) | 2007-06-27 |
RU2008130407A (ru) | 2011-02-20 |
RU2482136C2 (ru) | 2013-05-20 |
US20100040894A1 (en) | 2010-02-18 |
CA2634837A1 (en) | 2007-07-05 |
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