EP4058495A1 - Feuchtigkeitshärtender polyurethanheissklebstoff mit hoher anfänglicher festigkeit - Google Patents
Feuchtigkeitshärtender polyurethanheissklebstoff mit hoher anfänglicher festigkeitInfo
- Publication number
- EP4058495A1 EP4058495A1 EP20803587.3A EP20803587A EP4058495A1 EP 4058495 A1 EP4058495 A1 EP 4058495A1 EP 20803587 A EP20803587 A EP 20803587A EP 4058495 A1 EP4058495 A1 EP 4058495A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- moisture
- isocyanate
- melt adhesive
- polyurethane hot
- curing polyurethane
- 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- Withdrawn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
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- 229920002635 polyurethane Polymers 0.000 title claims abstract description 55
- 239000004831 Hot glue Substances 0.000 title claims abstract description 43
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 239000007858 starting material Substances 0.000 claims abstract description 32
- 239000012948 isocyanate Substances 0.000 claims abstract description 28
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 26
- 229920000747 poly(lactic acid) Polymers 0.000 claims abstract description 26
- 239000000203 mixture Substances 0.000 claims abstract description 23
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 13
- 239000000758 substrate Substances 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 238000002156 mixing Methods 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 3
- 230000008569 process Effects 0.000 claims abstract description 3
- 238000013008 moisture curing Methods 0.000 claims description 41
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 35
- 150000003077 polyols Chemical class 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 20
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 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 10
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- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229920001228 polyisocyanate Polymers 0.000 description 4
- 239000005056 polyisocyanate Substances 0.000 description 4
- JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- JJTUDXZGHPGLLC-ZXZARUISSA-N (3r,6s)-3,6-dimethyl-1,4-dioxane-2,5-dione Chemical compound C[C@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-ZXZARUISSA-N 0.000 description 2
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 description 2
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 2
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 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
- 239000004359 castor oil Substances 0.000 description 2
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- 239000003795 chemical substances by application Substances 0.000 description 2
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-QXMHVHEDSA-N gadoleic acid Chemical compound CCCCCCCCCC\C=C/CCCCCCCC(O)=O LQJBNNIYVWPHFW-QXMHVHEDSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008169 grapeseed oil Substances 0.000 description 1
- 239000010460 hemp oil Substances 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical group OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- TXXWBTOATXBWDR-UHFFFAOYSA-N n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCN(C)C TXXWBTOATXBWDR-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000010466 nut oil Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 238000013386 optimize process Methods 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 235000020233 pistachio Nutrition 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000001944 prunus armeniaca kernel oil Substances 0.000 description 1
- 239000008171 pumpkin seed oil Substances 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- JIWBIWFOSCKQMA-UHFFFAOYSA-N stearidonic acid Natural products CCC=CCC=CCC=CCC=CCCCCC(O)=O JIWBIWFOSCKQMA-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- AQWHMKSIVLSRNY-UHFFFAOYSA-N trans-Octadec-5-ensaeure Natural products CCCCCCCCCCCCC=CCCCC(O)=O AQWHMKSIVLSRNY-UHFFFAOYSA-N 0.000 description 1
- UWHZIFQPPBDJPM-BQYQJAHWSA-N trans-vaccenic acid Chemical compound CCCCCC\C=C\CCCCCCCCCC(O)=O UWHZIFQPPBDJPM-BQYQJAHWSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 239000008170 walnut oil Substances 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/08—Polyurethanes from polyethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/06—Polyurethanes from polyesters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—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
- C08G18/30—Low-molecular-weight compounds
- C08G18/302—Water
- C08G18/307—Atmospheric humidity
-
- 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
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
-
- 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
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4063—Mixtures of compounds of group C08G18/62 with other macromolecular compounds
-
- 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
- C08G18/4202—Two or more polyesters of different physical or chemical nature
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/428—Lactides
-
- 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
- C08G18/48—Polyethers
- C08G18/4825—Polyethers containing two hydroxy 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
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
-
- 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
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
- C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
-
- 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
- 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
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
- C09J5/06—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving heating of the applied adhesive
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2170/00—Compositions for adhesives
- C08G2170/20—Compositions for hot melt adhesives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2475/00—Presence of polyurethane
Definitions
- the present invention relates to a moisture-curing polyurethane hot-melt adhesive containing at least 80% by weight, based on the total weight of the moisture-curing polyurethane hot-melt adhesive, prepolymer terminated with isocyanate groups, which is obtainable by mixing diisocyanate (a) with compounds having at least two isocyanate-reactive compounds Groups (b) and converting the mixture to the prepolymer terminated with isocyanate groups, the compounds with at least two isocyanate-reactive groups (b) containing at least one polylactide (bl) which is obtainable by reacting lactide with a linear, difunctional one Starter molecule with 2 to 20 carbon atoms and the isocyanate content of the prepolymer terminated with isocyanate groups is 1 to 5% by weight.
- the present invention also relates to a method for producing such a moisture-curing hot-dip polyurethane adhesive and its use for bonding substrates.
- Moisture-curing polyurethane hot-melt adhesives are known and are widely used. These mostly contain polyester-based prepolymers terminated with isocyanate groups, which are obtained by reacting an excess of diisocyanates, mostly based on isomers of diphenylmethane diisocyanate, with polyester oils. Their main advantages are the combination of a high initial strength and the ability to react with water and thus to cure effectively and to generate a highly effective bond after complete curing.
- polyesters that are used in the production of the polyester-based prepolymers terminated with isocyanate groups for the moisture-curing polyurethane hot-melt adhesives are amorphous polyester polyols with a glass transition temperature T g of usually greater than 20 ° C. aromatic diols and diacids he will keep, and crystalline, at 20 ° C solid Polyesteroie, which can be obtained, for example, by esterification of hexanediol and adipic acid. Such polyester films are commercially available.
- An example of such an amorphous polyester polyol is marketed by Evonik under the trade name Dynacoll® 7130, an example of a crystalline polyesterol is also marketed by Evonik under the trade name Dyna coll® 7360.
- the moisture-curing polyurethane hot-melt adhesive can contain not only the prepolymer terminated with isocyanate groups to optimize process properties, open time and initial strength, but also thermoplastic materials such as thermoplastic polyurethane, polyacrylates or other, preferably aliphatic resins. Efforts are currently being made to increase the proportion of renewable raw materials in moisture-curing polyurethane hot-melt adhesives.
- US 20170002241 discloses the use of glycerol and fatty acid glyceride-containing polylactides for producing the polyester-based prepolymer terminated with isocyanate groups.
- the disadvantage of the prepolymers terminated with isocyanate groups and described in US 2017/0002241 is their low initial strength. It was an object of the present invention to provide a moisture-curing hot-dip polyurethane adhesive with a high initial strength, the prepolymer terminated with isocyanate groups having a large proportion of renewable raw materials.
- the object of the invention has been achieved by a moisture-curing polyurethane hot-melt adhesive containing at least 80% by weight, based on the total weight of the moisture-curing polyurethane hot-melt adhesive, with isocyanate groups terminated prepolymer, which is obtainable by mixing diisocyanate (a) with compounds with at least two isocyanate groups reactive groups (b) and converting the mixture to the prepolymer terminated with isocyanate groups, the compounds with at least two isocyanate-reactive groups (b) containing at least one polylactide (bl) which is obtainable by reacting lactide with a linear, difunctional starter molecule with 2 to 20 carbon atoms and the isocyanate content of the prepolymer terminated with isocyanate groups is 1 to 5% by weight.
- the present invention also relates to a method for producing such a moisture-curing polyurethane hot-melt adhesive and its use for bonding substrates.
- a moisture-curing polyurethane hot-melt adhesive is understood as meaning a mixture containing an isocyanate group-containing prepolymer or the isocyanate-group containing prepolymer itself, where the mixture is at least 80% by weight, preferably at least 90% by weight and in particular at least 95% by weight of a prepolymer containing isocyanate groups.
- a moisture-curing polyurethane adhesive according to the invention can contain further additives such as surface-active substances such as mold release agents and / or defoamers, inhibitors such as diglycol bis-chloroformate or orthophosphoric acid, plasticizers, inorganic and / or organic fillers such as sand, kaolin, Chalk, barium sulfate, silicon dioxide and carbon black, oxidation stabilizers, melting aids such as thermoplastic polymers, dyes and pigments, stabilizers, e.g.
- prepolymer terminated with isocyanate groups is understood to mean the reaction product of diisocyanates (a) with compounds which have at least two isocyanate-reactive groups and optionally compounds with one isocyanate-reactive group, the diisocyanate being used in excess.
- diisocyanates for the preparation of the prepolymer containing isocyanate groups.
- isocyanates of higher functionality can also be used. If higher-functionality isocyanates are used, their proportion, based on the total weight of the isocyanates used, is preferably less than 40% by weight, particularly preferably less than 20% by weight, more preferably less than 10% by weight and in particular less than 1 Wt%. It is also preferred that no isocyanate of higher functionality is used.
- Aromatic bivalent or polyvalent isocyanates are preferably used. Examples are 4,4, 2,4 'and 2,2'-diphenylmethane diisocyanate (MDI), the mixtures of monomeric diphenylmethane diisocyanates and higher nuclear homologues of diphenylmethane diisocyanate (polymer MDI), tetramethylene diisocyanate, hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI) ), 1,5-naphthalene diisocyanate (NDI), 2,4,6-toluene triisocyanate and 2,4- and 2,6-toluene diisocyanate (TDI), or mixtures thereof.
- MDI 4,4, 2,4 'and 2,2'-diphenylmethane diisocyanate
- polymer MDI polymer MDI
- tetramethylene diisocyanate tetramethylene diisocyanate
- HDI
- aromatic isocyanates preferably selected from the group consisting of 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 2,4'-diphenylmethane diisocyanate and 4,4'-diphenylmethane diisocyanate, as well as mixtures of these isocyanates.
- aromatic isocyanate selected from the group consisting of 2,4′-diphenylmethane diisocyanate, 4,4′-diphenylmethane diisocyanate and mixtures of these isocyanates is used as the diisocyanate.
- the proportion of 4,4′-MDI is greater than 50% by weight, more preferably greater than 80% by weight and in particular greater than 95% by weight, based in each case on the total weight of the isocyanates used .
- isocyanate-reactive compounds (b) with at least two groups reactive toward isocyanates all compounds with at least two groups reactive toward isocyanate groups can be used for the preparation of the prepolymer containing isocyanate groups.
- Polyesteroie, polyetheroie or polyether-polyesterols which can be obtained, for example, by alkoxylation of polyesters, in particular polyesters, are preferably used.
- the isocyanate-reactive compounds (b) contain at least one polylactide (bl) which is obtainable by reacting lactide with a bifunctional, linear starter molecule with 2 to 20 carbon atoms.
- the mean OH functionality of the compounds (b) is preferably 1.8 to 2.2, particularly preferably 1.9 to 2.1 and in particular 2.
- the functionality here is understood to be the theoretical functionality based on the starting materials.
- Polyetheroie are lialkoholaten according to known processes, for example by anionic polymerization with alkali metal hydroxides or Al ka lialkoholaten as catalysts and with the addition of at least one starter molecule containing 2 to 5, preferably 2 to 4 and particularly preferably 2 to 3, in particular 2 reactive hydrogen atoms ge, or by cationic polymerization with Lewis acids, such as anti - monpentachloride or boron trifluoride etherate, prepared from one or more alkylene oxides with 2 to 4 carbon atoms in the alkylene radical.
- Lewis acids such as anti - monpentachloride or boron trifluoride etherate
- multimetal cyanide compounds so-called DMC catalysts, can also be used as catalysts.
- Suitable alkylene oxides are, for example, tetrahydrofuran, 1,3-propylene oxide, 1,2- or 2,3-butylene oxide and preferably ethylene oxide and 1,2-propylene oxide.
- the alkylene oxides can be used individually, alternately in succession or as mixtures. 1,2-propylene oxide, ethylene oxide or mixtures of 1,2-propylene oxide and ethylene oxide are preferably used.
- Suitable starter molecules are preferably water or di- and trihydric alcohols, such as ethylene glycol, 1,2- or 1,3-propanediol, diethylene glycol, dipropylene glycol, 1,4-butanediol, glycerol and trimethylolpropane.
- the polyether polyols can be obtained by alkoxylating a starter molecule with a functionality of 2.0 to 4.0, particularly preferably 2.0 and 3.0, more preferably 2.0 to 2 , 2 and in particular 2.0 and have an average ethylene oxide content, based on the total weight of alkylene oxide, of 20 to 70% by weight, preferably 25 to 60% by weight and in particular 30 to 50% by weight.
- the propylene glycol content is greater than 70% by weight, particularly preferably greater than 85% by weight and in particular greater than 95% by weight, based on the total weight of the alkylene oxides used to produce the polyetherol .
- the preferred polyetherols have a number average molecular weight of 400 to 9,000 g / mol, preferably 1,000 to 6,000, particularly preferably 1,500 to 5,000 and in particular 2,000 to 4,000 g / mol. Since an increase in the content of ethylene oxide and a reduction in functionality for the same molecular weight usually lead to a reduction in the viscosity of the polyether oil.
- hydrophobic polyols can be used which have at least one hydrophobic hydrocarbon moiety with at least 8 carbon atoms.
- a hydroxyl-functionalized oleochemical compound, a oleochemical polyol, is preferably used as the hydrophobic polyol.
- oils modified with hydroxyl groups such as grapeseed oil, black caraway oil, pumpkin seed oil, borage seed oil, soybean oil, wheat germ oil, rapeseed oil, sunflower oil, peanut oil, apricot kernel oil, pistachio kernel oil, almond oil, olive oil, macadamia nut oil, night rose oil, avocado oil , Hemp oil, safflower oil, walnut oil, fatty acid esters modified with hydroxyl groups based on myristoleic acid, palmitoleic acid, oleic acid, vaccenic acid, petroselinic acid, gadoleic acid, erucic acid, nervonic acid, linoleic acid, linolenic acid, stearidonic acid, arachidonic acid, cupanodonic acid, timnodonic acid.
- oils modified with hydroxyl groups such as grapeseed oil, black caraway oil, pumpkin seed oil, borage seed oil, soybean oil, wheat germ oil, rapeseed oil, sunflower oil
- Castor oil and its reaction products with alkylene oxides or ketone-formaldehyde resins are preferably used here.
- the latter compounds are sold, for example, by Bayer AG under the name Desmophen 0 1150.
- the isocyanate-reactive compounds with at least two isocyanate-reactive groups (b) contain hydrophobic polyether or polyester oils.
- the compounds (b) can optionally also contain chain extenders and / or crosslinking agents.
- the chain extenders and / or crosslinkers can be added before, together with or after the addition of the polyols.
- the chain extenders and / or crosslinkers used are substances with a molecular weight of preferably less than 400 g / mol, particularly preferably from 60 to 350 g / mol used, chain extenders having 2 hydrogen atoms reactive toward isocyanates and crosslinking agents 3 having hydrogen atoms reactive toward isocyanates. These can be used individually or in the form of mixtures. If chain extenders are used, 1,3- and 1,2-propanediol, dipropylene glycol, tripropylene glycol, 1,3-butanediol are particularly preferred.
- chain extenders, crosslinking agents or mixtures thereof are expediently used in amounts of 1 to 30% by weight, preferably 1.5 to 20% by weight and in particular 2 to 10% by weight, based on weight of polyisocyanates, polymeric isocyanate-reactive compounds and chain extenders and / or crosslinking agents are used, preferably no chain extenders and / or crosslinking agents are used.
- the polylactide (bl) can be obtained by reacting lactide with a linear, difunctional starter molecule with 2 to 20 carbon atoms.
- the starter molecule is preferably selected from the group consisting of linear, aliphatic dialcohols, ethers of linear, aliphatic dialcohols, cycloaliphatic dialcohols and aromatic dialcohols.
- linear means that the starter molecule does not have any side groups with more than 7 atoms that branch off from the atoms that form the direct connection between the two OH groups.
- linear starter molecules are preferably selected from the group consisting of monoethylene glycol, diethylene glycol, propanediol, neopentyl glycol, dipropylene glycol, butanediol, pentanediol, hexanediol, heptanediol, octanediol, nonanediol, decanediol, dodecanediol and mixtures of two or more compounds thereof.
- the linear starter molecule contains 1,6-hexanediol; in particular, 1,6-hexanediol is used exclusively as the linear starter molecule.
- the linear starter molecule is usually reacted with the lactide in bulk, preferably using a metal catalyst, for example a tin catalyst or so-called double metal cyanide catalysts (also referred to as “DMC catalysts”).
- DMC catalysts are known and have already been described frequently in the prior art.
- lactide any form can be used as the lactide, for example L-lactide, D-lactide, meso-lactide or any mixture thereof.
- L-lactide, D-lactide or meso-lactide each in purities of preferably greater than 90% by weight, is preferably used.
- other alkylene oxides such as ethylene oxide, 1,3 or preferably 1,2-propylene oxide or 1,2- or 2,3-butylene oxide and particularly preferably 1,2-propylene oxide, can also be used. If alkylene oxides are used in addition to the lactide, this is preferably done in a block structure.
- the alkylene oxides are particularly preferably used as the end block, which is hot, the starter molecule is unset with the lactide in a first step and then the polymer obtained is kettenverlän gert in a second step with the alkylene oxide.
- the proportion of lactide groups, based on the total weight of the polylactide (bl) groups attached to the starter molecule is 50 to less than 100, preferably 70 to 99.5% by weight.
- the proportion of lactide groups, based on the total weight of the polylactide (b1) groups attached to the starter molecule is particularly preferably 100% by weight.
- the hydroxyl number of the polylactide (bl) is preferably 35 to 230 mg KOH / g.
- the compounds with at least two isocyanate-reactive groups (b) contain, in addition to the polylactide (bl), further polyols (b2) which are different from the polylactide (bl).
- polylactide (bl) include the above-described polyetherols, polyesters, hydrophobic polyols and polyetheresters, the number-average molecular weights of the polyols (b2) being at least 500 g / mol.
- the compounds (b2) preferably have a functionality of 2 to 4, particularly preferably 2 to 3 and in particular 2.
- the polyols (b2) contain a mixture of one or more polyether polyols (b2a) and one or more polyester polyols (b2b).
- the polyether polyols (b2a) and polyesteroie (b2b) have preferably a number average molecular weight of 1500 to 6000 g / mol, particularly preferably 2000 to 4000 g / mol.
- the polyester (b2b) is a polyester which was obtained starting from hexanediol, in particular 1,6-hexanediol, as the diol component.
- the polyether (b2a) used is preferably a polyether which is at least 50% by weight, preferably at least 70% by weight, particularly preferably at least 85% by weight, more preferably at least 95% by weight and in particular exclusively propylene oxide , based on the alkylene oxides used to prepare the polyether (b2a).
- the component (b2) contains, besides the polyethers (b2a) and the polyesters (b2b), no further compounds with at least two isocyanate-reactive groups.
- the proportion of polylactide (bl), based on the total weight of the compounds with at least two isocyanate-reactive groups (b), is preferably 5 to 90% by weight, particularly preferably 10 to 80% by weight, more preferably 15 to 50% by weight .-% and in particular 20 to 40% by weight.
- the proportion of component (b2) is preferably 10 to 95% by weight, particularly preferably 20 to 90% by weight, more preferably 50 to 85% by weight and in particular 60 to 80% by weight, the ratio being from Polyether (b2a) to polyester (b2b) is preferably 4: 1 to 1: 2, particularly preferably 3: 1 to 1: 1.
- component (b) particularly preferably contains less than 10% by weight, particularly preferably less than 5% by weight and in particular no further compounds having at least two hydrogen atoms reactive toward isocyanate groups.
- polyether monools which are obtained starting from monofunctional starter molecules, for example ethylene glycol monomethyl ether, analogously to the polyether oils described above.
- the molecular weight of the polyether monools is preferably 100 to 1000 g / mol. If polyether monools are used, the weight ratio of polyether monool to the compounds (b) is preferably from 1:30 to 4: 1, and it is particularly preferred not to use any compounds with only one isocyanate-reactive group.
- customary polyurethane catalysts preferably amine-containing polyurethane catalysts
- amine-containing polyurethane catalysts can also be used to produce the prepolymer containing isocyanate groups.
- Such catalysts are described, for example, in "Kunststoffhandbuch, Volume 7, Polyurethane", Carl Hanser Verlag, 3rd Edition 1993, Chapter 3.4.1.
- the catalysts preferably contain strongly basic amine catalysts.
- amidines such as 2,3-dimethyl-3,4,5,6-tetrahydropyrimidine
- tertiary amines such as triethylamine, tributylamine, dimethylbenzylamine, N-methyl-, N-ethyl-, N-cyclohexylmorpholine, N, N, N ', N'-tetramethylethylenediamine, N, N, N', N'-tetramethyl-butanediamine, N, N, N ', N'-tetramethyl-hexanediamine, Pentamethyl diethylenetriamine, tetra methyl diaminoethyl ether, bis (dimethylaminopropyl) urea, dimethylpiperazine, 1,2-dimethylimidazole, 1-azobicyclo- (3,3,0) octane and preferably 1,4-diaza -bicyclo- (2,2,2) -octane and alkanolamine
- the polyisocyanates described are used in excess, for example at temperatures from 30 to 100 ° C., preferably at about 80 ° C., with the compounds with at least two isocyanate-reactive groups, optionally compounds with one isocyanate-reactive Group converted to prepolymer.
- the mixing ratio of polyisocyanates, polymeric compounds with at least two isocyanate-reactive groups, optionally compounds with an isocyanate-reactive group and optionally chain extenders and / or cross-linking agents is chosen so that the isocyanate content (NCO content) of the The prepolymer produced is in the range from 1 to 5, preferably 1.2 to 3, particularly preferably 1.5 to 2.5 and in particular 1.6 to 2.0% by weight, based on the total weight of the isocyanate prepolymer produced. If necessary, volatile isocyanates can then be separated off, preferably by thin-film distillation.
- the viscosity of the isocyanate prepolymers according to the invention is preferably from 5 to 1000 Pas, more preferably from 10 to 300 Pas and in particular from 15 to 200 Pas, in each case at 40.degree. C. This can be achieved, for example, by setting the isocyanate index, the average functionality and the polyols and isocyanates used can be adjusted. These modifications are known to those skilled in the art.
- the average isocyanate functionality of the isocyanate prepolymers is preferably 2.0 to 2.9, particularly preferably 2.0 to 2.2.
- melting aids such as thermoplastic polymers in the manufacture of moisture-curing polyurethane hot-melt adhesives, is generally known.
- the polyurethane hot-melt adhesive according to the invention contains thermoplastic polymer which has no isocyanate-reactive groups. All thermoplastics can be used for this.
- the thermoplastics preferably have a
- thermoplastics are thermoplastic polyurethane and polyacrylates or polyester, particularly preferably thermoplastic polyurethane and / or polyacrylates are used as thermoplastics.
- the polyurethane hot-melt adhesive according to the invention can be used for bonding substrates, for example by applying the moisture-curing polyurethane hot-melt adhesive to at least one substrate at temperatures of greater than 80 ° C., preferably 90 to 200 ° C., more preferably 100 to 150 ° C., applying a second one Substrate on the moisture-curing polyurethane hot-melt adhesive and let the moisture-curing polyurethane hot-melt adhesive cure, preferably at temperatures of less than 100 ° C.
- the hot-melt polyurethane adhesive according to the invention has very good adhesion and a rapid increase in viscosity when cooling to temperatures below 110 ° C., which results in a very good adhesion good initial strength of the adhesive bond is obtained. Furthermore, he inventive polyurethane hot melt adhesives have good adhesion and strength of the cured adhesive bond, very good hydrolysis resistance and a high content of bio-based raw materials. Substrates can be materials such as wood, glass, metals, textiles, plastics and natural materials such as fibers. Textiles are particularly preferably bonded to fiber-reinforced polyurethane plastics.
- Moisture-curing polyurethane adhesives according to the present invention (examples according to the invention) and comparative examples were produced and the increase in viscosity during hardening was investigated.
- Polyesterol 1 Polyesterol made from hexanediol and adipic acid with a functionality of 2, a hydroxyl number of 30 mg KOH / g and a melting point of 55 ° C., available under the trade name Dynacoll ⁇ 7360 from Evonic
- Polyetherol 1 polypropylene glycol with a functionality of 2 and a hydroxyl number of 56 mg KOH / g
- Polyetherol 2 polypropylene glycol with a functionality of 2 and a hydroxyl number of 28 mg KOH / g
- lactide polyols were prepared by reacting a starter containing OH groups with Puralact L ((3S-cis) -3,6-dimethyl-1,4-dioxane-2,5-dione,
- Lactide polyol 1 Polylactide with 1,6-hexanediol as a starter molecule, a functionality of 2 and a hydroxyl number of 56 mg KOH / g, produced using 100 ppm tin bis (2-ethylhexanoate) at 175 ° C (based on the amount of catalyst Overall approach).
- Lactide polyol 2 Polylactide with 1,6-hexanediol as a starter molecule, a functionality of 2 and a hydroxyl number of 56 mg KOH / g, produced using double metal cyanide catalyst (1000 ppm based on the total batch) at 200 ° C (catalyst amount based on the total batch).
- Lactide polyol 3 Polylactide with neopentyl glycol as the starter molecule, a functionality of 2 and a hydroxyl number of 56 mg KOH / g, produced using 100 ppm tin bis (2-ethylhexanoate) at 175 ° C (amount of catalyst based on total batch).
- Lactide polyol 4 Polylactide with neopentyl glycol as a starter molecule, a functionality of 2 and a hydroxyl number of 37 mg KOH / g, produced using 100 ppm tin catalyst at 175 ° C.
- Acrylate polymer Thermoplastic acrylate polymer with a number average molecular weight of 34,000 g / mol, available under the trade name Elvacite ⁇ 2013 from Lucite International.
- Isocyanate MDI mixture containing approx. 99% by weight 4,4‘-MDI and approx. 1% by weight 2,4‘-M Dl
- the viscosities of the moisture-curing polyurethane adhesives obtained were determined based on ASTM D 3236 at different temperatures in a Brookfield viscometer with one-time measuring geometry spindle SC27 be determined. These values are given in Table 2.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
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PCT/EP2020/082002 WO2021094509A1 (de) | 2019-11-15 | 2020-11-13 | Feuchtigkeitshärtender polyurethanheissklebstoff mit hoher anfänglicher festigkeit |
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DE102013205110A1 (de) * | 2013-03-22 | 2014-09-25 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Klebstoffzusammensetzung auf Basis eines Polyesterurethans und Polyesterurethan |
WO2017003875A1 (en) | 2015-07-01 | 2017-01-05 | H.B. Fuller Company | Moisture curable adhesive composition based on polylactide polyols |
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