WO2008071307A1 - Klebstoffe - Google Patents
Klebstoffe Download PDFInfo
- Publication number
- WO2008071307A1 WO2008071307A1 PCT/EP2007/010345 EP2007010345W WO2008071307A1 WO 2008071307 A1 WO2008071307 A1 WO 2008071307A1 EP 2007010345 W EP2007010345 W EP 2007010345W WO 2008071307 A1 WO2008071307 A1 WO 2008071307A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- isocyanate
- reactive
- preparation
- polymer
- latent
- Prior art date
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 25
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 25
- 239000012948 isocyanate Substances 0.000 claims abstract description 72
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 65
- 239000006185 dispersion Substances 0.000 claims abstract description 43
- 239000000843 powder Substances 0.000 claims abstract description 40
- 238000000576 coating method Methods 0.000 claims abstract description 28
- 239000002245 particle Substances 0.000 claims abstract description 24
- 239000007787 solid Substances 0.000 claims description 48
- 238000002360 preparation method Methods 0.000 claims description 43
- 229920000642 polymer Polymers 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 28
- 125000001931 aliphatic group Chemical group 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 25
- 230000008569 process Effects 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000005056 polyisocyanate Substances 0.000 claims description 14
- 229920001228 polyisocyanate Polymers 0.000 claims description 14
- 229920013730 reactive polymer Polymers 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 238000009472 formulation Methods 0.000 claims description 13
- 239000000758 substrate Substances 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 9
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical group CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000004745 nonwoven fabric Substances 0.000 claims description 8
- 229920000728 polyester Polymers 0.000 claims description 8
- 239000013638 trimer Substances 0.000 claims description 8
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 7
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229910052750 molybdenum Inorganic materials 0.000 claims description 5
- 239000011733 molybdenum Substances 0.000 claims description 5
- 230000000737 periodic effect Effects 0.000 claims description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 229910052720 vanadium Inorganic materials 0.000 claims description 4
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 4
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000012071 phase Substances 0.000 claims description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 239000010408 film Substances 0.000 description 34
- 239000003054 catalyst Substances 0.000 description 33
- 238000004132 cross linking Methods 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 24
- 230000004913 activation Effects 0.000 description 12
- 239000012790 adhesive layer Substances 0.000 description 11
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 11
- -1 cycloaliphatic Chemical group 0.000 description 10
- 239000004815 dispersion polymer Substances 0.000 description 10
- 238000005304 joining Methods 0.000 description 10
- 239000010410 layer Substances 0.000 description 9
- 239000004814 polyurethane Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 239000004971 Cross linker Substances 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000012545 processing Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229920002635 polyurethane Polymers 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 229910052797 bismuth Inorganic materials 0.000 description 5
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 5
- 239000002131 composite material Substances 0.000 description 5
- 230000009849 deactivation Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000004823 Reactive adhesive Substances 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 229920002396 Polyurea Polymers 0.000 description 3
- 239000002313 adhesive film Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000011805 ball Substances 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- NMHMDUCCVHOJQI-UHFFFAOYSA-N lithium molybdate Chemical compound [Li+].[Li+].[O-][Mo]([O-])(=O)=O NMHMDUCCVHOJQI-UHFFFAOYSA-N 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 229920003009 polyurethane dispersion Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 230000002123 temporal effect Effects 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000002981 blocking agent Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000011133 lead Substances 0.000 description 2
- 150000002611 lead compounds Chemical class 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 229910052715 tantalum Inorganic materials 0.000 description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 2
- 230000000930 thermomechanical effect Effects 0.000 description 2
- 239000011135 tin Substances 0.000 description 2
- 238000005829 trimerization reaction Methods 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- 150000003752 zinc compounds Chemical class 0.000 description 2
- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 description 2
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 240000000731 Fagus sylvatica Species 0.000 description 1
- 235000010099 Fagus sylvatica Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical compound [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000003373 anti-fouling effect Effects 0.000 description 1
- 150000001463 antimony compounds Chemical class 0.000 description 1
- 230000000386 athletic effect Effects 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- AAQNGTNRWPXMPB-UHFFFAOYSA-N dipotassium;dioxido(dioxo)tungsten Chemical compound [K+].[K+].[O-][W]([O-])(=O)=O AAQNGTNRWPXMPB-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- MODMKKOKHKJFHJ-UHFFFAOYSA-N magnesium;dioxido(dioxo)molybdenum Chemical compound [Mg+2].[O-][Mo]([O-])(=O)=O MODMKKOKHKJFHJ-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical class O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000011527 polyurethane coating Substances 0.000 description 1
- 229920003226 polyurethane urea Polymers 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- UYLYBEXRJGPQSH-UHFFFAOYSA-N sodium;oxido(dioxo)niobium Chemical compound [Na+].[O-][Nb](=O)=O UYLYBEXRJGPQSH-UHFFFAOYSA-N 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- SZWHXXNVLACKBV-UHFFFAOYSA-N tetraethylphosphanium Chemical class CC[P+](CC)(CC)CC SZWHXXNVLACKBV-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- SYRHIZPPCHMRIT-UHFFFAOYSA-N tin(4+) Chemical class [Sn+4] SYRHIZPPCHMRIT-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
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000723 toxicological property Toxicity 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
- WQEVDHBJGNOKKO-UHFFFAOYSA-K vanadic acid Chemical class O[V](O)(O)=O WQEVDHBJGNOKKO-UHFFFAOYSA-K 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- GBNDTYKAOXLLID-UHFFFAOYSA-N zirconium(4+) ion Chemical class [Zr+4] GBNDTYKAOXLLID-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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
-
- 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
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/222—Catalysts containing metal compounds metal compounds not provided for in groups C08G18/225 - C08G18/26
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—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
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
- C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
- C08G18/722—Combination of two or more aliphatic and/or cycloaliphatic polyisocyanates
-
- 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
- C08G2170/80—Compositions for aqueous 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.]
Definitions
- the invention relates to adhesives based on aqueous dispersions and surface-deactivated isocyanate particles as well as latent-reactive coatings, films and powders produced from such dispersions.
- Polyurethane dispersion polymers which have linear polymer chains which crystallize at temperatures below 100 ° C are described i.a. used for heat-activated bonding of temperature-sensitive substrates.
- 1-component processing i. however, without the addition of a crosslinker, only low heat resistances correlated with the decalcification temperature or softening temperature of the polymer are achieved.
- the hydrolysis resistance in 1-component processing is insufficient for many applications.
- the aqueous dispersion polymers are usually processed with the concomitant use of liquid, hydrophilic modified polyisocyanates.
- the gain in improved properties is paid for with a higher technical outlay for the two-component processing.
- the preparation of the two-component mixture must be carried out immediately before the dispersion is processed.
- the two-component processing is prone to error in addition of the proper amount of isocyanate component and homogeneous co-agitation of the isocyanate component.
- the pot life of the two-component mixture is, depending on the type of polymer dispersion or isocyanate component 1 - 12 hours.
- the dried adhesive layers must be processed within about 1-12 h, otherwise - due to the progressive crosslinking reaction by the isocyanate groups - Polymer can no longer be processed under the usual conditions of heat-induced bonding.
- latent-reactive dispersion adhesives consist of at least one dispersion of isocyanate-reactive polymers and solid isocyanate particles.
- Aqueous preparations of isocyanate-reactive polymer dispersions having finely dispersed, surface-deactivated, uretdione-containing oligomeric solid isocyanates and their use as latently reactive binders for coatings and for adhesives have been known for some years.
- Surface-deactivated isocyanate particles are to be understood as meaning those solid isocyanates in which 0.1-25, preferably 0.5-8, equivalent percent of the total isocyanate groups present in the isocyanate particles are reacted with a deactivating agent.
- the deactivation of the isocyanate particles can be effected inter alia by the deactivating agents described in EP-A 0 204 970, US Pat. No. 4,595,445 and DE 10140206.
- the surface-deactivated isocyanate particles differ fundamentally from the blocked isocyanates. In the case of the surface-deactivated isocyanate particles, preference is given to 92-99.5 equivalent percent of the isocyanate groups being free. In the blocked isocyanates, however, all isocyanate groups are reacted with a blocking agent. For the crosslinking reaction, the isocyanate groups of the blocked isocyanate must be replaced by e.g. Cleavage of the blocking agent are released first. In the case of the surface-deactivated isocyanate particles, the deblocking reaction of the isocyanate groups is not necessary.
- EP-A 0 204 970 describes a process for preparing stable dispersions of finely divided polyisocyanates by treating the polyisocyanates in a liquid with stabilizers and action of high shear forces or milling.
- di- and polyisocyanates are suitable whose melting point is above 10 0 C, preferably above 40 0 C.
- the dispersions described are used as crosslinkers.
- EP-A 1 172 390 discloses storage-stable isocyanate dispersions consisting of deactivated isocyanates and isocyanate-reactive polymers which crosslink after removal of the water at temperatures between 5 ° C. and 40 ° C.
- the aqueous dispersion preparations are characterized by good lab stability.
- the disadvantage of the procedure described in this publication is that the largely dry coatings, films or powders are not stable in storage.
- the crosslinking reaction begins with the drying of the layers.
- the desired spatial and temporal separation of the processing steps application / drying of the dispersion layer and joining of the composites can with this
- EP-A 1 134 245 describes storage-stable preparations of finely divided di- and polyisocyanate powders which can be incorporated directly into the aqueous isocyanate-reactive polymer dispersions without surface deactivation.
- the crosslinking reaction in these formulations is initiated by heating the dried layer to a temperature of at least 65 ° C.
- EP-A 0 922 720 discloses the use of aqueous dispersions which contain at least one surface-deactivated polyisocyanate and at least one isocyanate-reactive polymer for the preparation of storage-stable, latently reactive layers or powders which are stable at room temperature
- Heating can be brought to crosslinking.
- polyisocyanates all the aliphatic, cycloaliphatic, heterocyclic or aromatic isocyanates can be used, which have a melting point above 40 0 C.
- the stability of the precoat, the films or the powders and their reaction rate in the heat-induced crosslinking can be influenced by the type of isocyanate, by the amount of surface stabilizer, by the solubility parameters of the dispersion polymer and by catalysts.
- the catalysts mentioned are the typical polyurethane catalysts such as tin, iron, lead, cobalt, bismuth, antimony and zinc compounds or their mixtures, alkylmercaptide compounds of dibutyltin and tertiary amines.
- aliphatic isocyanates or polyurethanes based on aliphatic isocyanates do not absorb the short-wave UV component of the sunlight, these polyurethanes are principally protected against yellowing.
- latent-reactive films or latent-reactive powders therefore, the use of surface-deactivated aliphatic solid isocyanates is particularly advantageous.
- aliphatic isocyanates a disadvantage of the aliphatic isocyanates is the known lower reactivity compared to the aromatically bound isocyanate groups. This is for example from Ullmann's Encyclopedia of Industrial Chemistry, Sixth Edition, Vol. 18, p. 609, Wiley-VCH Verlag, 2002, Isocyanantes, Organic, known. For this reason, no applications of latent-reactive coatings, films or powders based on deactivated aliphatic solid isocyanates have yet been established. Thus, the relative reactivity of the free isocyanate group of the isocyanurate from isophorone diisocyanate (IPDI) over OH groups is about a factor of about 50 lower than the reactivity of the free isocyanate groups of the aromatic 1
- IPDI isophorone diisocyanate
- Methyl 2,4-phenylene diisocyanate (TDI dimer) towards OH groups Methyl 2,4-phenylene diisocyanate (TDI dimer) towards OH groups.
- Latent-reactive coatings, films or powders according to EP-A 0 922 720 which contain a deactivated aliphatic solid isocyanate as crosslinking component, require either a) a very long residence time at high temperatures in order to crosslink the isocyanate-reactive polymer so as to lead the crosslinking reaction to such an extent b) a catalyst which accelerates the reaction between the aliphatic isocyanate groups and the isocyanate-reactive polymer so that the crosslinking reaction proceeds even after a short heat exposure to the desired crosslinking density. Without a catalyst, the crosslinking reaction takes place in these storage-stable latent-reactive layers,
- a latent-reactive film prepared using the aliphatic IPDI trimer as a solid isocyanate must be allowed to dry for at least 30 minutes. be kept at 120 0 C to achieve a sufficiently high crosslink density in the adhesive bond.
- the catalysts listed in EP-A 0 922 720 are typical for isocyanate reactions used catalysts. In particular, however, these catalysts have disadvantages in their use in the preparation of latent-reactive coatings, latent-reactive films or latent-reactive powders, making their use impossible.
- the organic Zn (IV) compounds such as DBTL are generally contaminated with dibutyltin and tributyltin, respectively, as described in "Assessment of the risk to health and environment of the use of organostannic compounds (excluding biocides in antifouling paints) and a Description of the Economic Profile of the Industry, Final Report 19 June 2002, European Commission Health & Consumer Protection Directorate-General ". From an ecological point of view, the use of Zn (IV) compounds is not desirable.
- the organic Zn (IV) compounds also catalyze the hydrolysis of the polyester polyurethane polymer chain polyester segments as used for the isocyanate-reactive dispersion polymers in latent-reactive layers. For this reason, organi- see Zn (IV) compounds for the catalysis of the reaction of surface-deactivated aliphatic solid isocyanates with crystalline isoeyanatreepte polyurethane dispersion polymers based on polyester polyol can not be used.
- prior art catalysts typically have only a finite lifetime in aqueous systems, i. the catalyst is hydrolyzed by the action of water more or less rapidly. This applies to the aqueous preparation of surface-deactivated aliphatic solid isocyanates and isocyanate-reactive dispersed polymers as well as for the substantially dry latent-reactive coatings, which usually still has a residual moisture content of about 0.6 to 1.0 wt.% Water based on have the weight of the coating.
- tin (IV) compounds which are frequently used in conventional systems, such as the abovementioned DBTL or else bismuth carboxylates, such as, for example, Bismuth (IH) -2-ethylhexanoate (K-Kat, King Industries, Norwalk, Conn., USA), as also described in WO 00/047642.
- bismuth carboxylates such as, for example, Bismuth (IH) -2-ethylhexanoate (K-Kat, King Industries, Norwalk, Conn., USA), as also described in WO 00/047642.
- the lead and antimony compounds are also not advantageous due to their toxicology and their environmentally harmful effect and therefore should not be used in principle.
- Another problem for catalyzing the reaction between surface-deactivated solid isocyanate and isocyanate-reactive dispersion polymer is the ionic groups required to hydrophilize the polymer chain of the dispersion polymer. Hydrophilization can be achieved by incorporating carboxyl groups into the polymer chain. These carboxyl groups may possibly lead to an inhibition of the catalytic activity of organotin compounds by a complex formation. This is true for all highly charged Lewis acids, e.g. Titanium (IV), zirconium (IV) compounds.
- a catalyst which is said to be universally useful with a variety of surface-deactivated aliphatic solid isocyanates, polyisocyanates and hydrophilic binders must not show these interactions with the hydrophilizers.
- EP-A 1 599 525 describes catalysts for the accelerated curing of polyisocyanates with polyols and polyurethane systems containing them.
- the (poly) -isocyanate components which can be used according to this teaching are any organic polyisocyanates with aliphatic, cycloaliphatic, araliphatic and / or or aromatically bound, free isocyanate groups that are liquid at room temperature or are diluted with solvent for this purpose.
- the (poly) -isocyanate component has a viscosity of 10 - 15,000 mPas at 23 ° C.
- the invention relates to catalysts for accelerated curing of polyisocyanates with polyols in the presence of the solvent water (so-called aqueous two-component polyurethane coatings, 2K-PUR water-based paints).
- the object of this invention was to find it catalysts which accelerate the reaction between the isocyanate and the alcohol or the polyol in the presence of water or to accelerate the curing of aqueous 2K-PUR systems, without having an effect on the pot life ,
- This object is achieved by the use of various salts of elements of the 5th and 6th (sub) group of the periodic table, in which the respective element has an oxidation state of at least +4.
- EP-A 0 992 720 also lists tertiary amines as effective catalysts.
- the tertiary amines lose their activity by absorption of carbon dioxide from the air.
- this fact is particularly undesirable because it is precisely the storage stability of the coatings, films or powders, also with regard to the crosslinking speed, which is essential for the use of the latent-reactive layers.
- the catalysts should also be positively evaluated in terms of their toxicological properties.
- the crosslinking reaction in the coatings, films or powders should be achieved in an application-technically acceptable time of heat activation.
- compositions according to the invention are therefore mixtures of: a) an aqueous dispersion or dispersion mixture of at least one polymer having isocyanate-reactive groups b) a surface-deactivated, finely divided aliphatic solid polyisocyanate at least substantially suspended in water c) at least one compound of elements of groups 5 and 6 of the Periodic Table, in which the respective element has an oxidation state of at least +4 and d) optionally further additives and auxiliaries.
- latent-reactive aqueous preparations according to the invention can be prepared in any desired manner, e.g. in the spray, doctor blade, brush, or roller application method on flat or three-dimensional
- release paper eg silicone paper or polyolefin non-sticky paper or similar support materials
- spray, knife, brush or roller application After drying, self-supporting latent-reactive films or nonwovens are obtained, which may be wound up after insertion of a release paper and stored until use as an adhesive film.
- the solids can be obtained in the form of granuta or powder by suitable technical processes.
- the formulations according to the invention can be freed from the water by spray-drying. This gives latent-reactive powders, which can be ground to small particle sizes, if necessary, by a subsequent grinding process.
- Latent-reactive powders can also be obtained by coagulation of polymer dispersions with surface-deactivated solid isocyanate particles.
- polyvalent cations eg Ca 2+ , Mg 2+ , Al 3+
- Centrifugation etc. largely freed from water and then dried at temperatures below the reaction temperature of the deactivated aliphatic solid isocyanate. Possibly. can the coagulum can be ground to the required particle size after drying in a milling process, eg in ball, bead, sand or jet mills.
- a further possibility for producing latent-reactive powders is to freezing of the mixture of polymer and devisfestdegentierem solid isocyanate from the aqueous prepara- obligations at temperatures below 0 0 C.
- the precipitated polymer / isocyanate mixture is then from the water by filtration, centrifugation etc. extensively freed and finally dried.
- the coarse-grained powder obtained can then be ground to the required particle sizes by suitable grinding - if necessary, the grinding process must take place at low temperatures - eg in ball, bead, sand or jet mills.
- the drying of the latent-reactive coatings, films, nonwovens or powder must be carried out at temperatures below the softening temperature of the polymer or the melting or the softening temperature of the surface-deactivated aliphatic solid isocyanate.
- the lowest of the softening or melting temperatures is to be used. If one of these temperatures is exceeded, then this inevitably leads to crosslinking of the polymer.
- the largely dry latent-reactive coatings, films or powders still have a residual moisture content of 0.1-5%.
- the aqueous dispersions for the preparations according to the invention preferably contain, as isocyanate-reactive dispersion polymer, polyurethane or polyurea dispersions with crystalline polyester soft segments. Particularly preferred are dispersions of isocyanate-reactive Polyu- rethanpolymere of crystalline polymer chains, which when measured by thermomechanical analysis at temperatures between 5O 0 C and 12O 0 C, at least partially dekristall ensue.
- Solid-isocyanates are all aliphatic and cycloaliphatic di- and polyisocyanates having a softening temperature> 4O 0 C.
- the aliphatic solid isocyanates according to the invention must be ground with customary grinding processes, for example in ball, bead, sand, disk or jet mills, to the particle sizes d50 ⁇ 100 ⁇ m, preferably d50 ⁇ 10 ⁇ m and particularly preferably d50 ⁇ 2 ⁇ m.
- the suspended surface-deactivated isocyanates can be prepared by the methods known from EP-A 0 992 720 and EP-A 1 172 390.
- catalysts it is generally possible to use chemical compounds of elements of groups 5 and 6 of the Periodic Table in which the respective element has an oxidation state of at least + 4.
- salts of these elements are used in which they have the said oxidation states.
- compounds of the elements vanadium, niobium, tantalum, molybdenum and tungsten have proven to be suitable, which are therefore preferably used.
- Such compounds of the elements vanadium, tantalum, molybdenum and tungsten are, for example, salts of molybdic acid, such as the alkali metal salts of molybdenic acid, and the alkali metal salts of vanadic acid and tetraethylphosphonium molybdate,
- the catalysts used according to the invention are also distinguished by a certain latency phase (delayed use of the catalytic effect) during heat activation.
- This effect which is advantageous for latent-reactive (pre) coatings, films, nonwovens or powders, ensures that the catalyst can not influence the storage stability of the latently reactive layers, films, nonwovens or powders.
- FIG. 1 shows an example of this phenomenon by the development of the memory module of two adhesive films (Dispercoll ® U 53 with Desmodur ® Z XP 2589 (mikonisier- tes IPDI trimer with 3 mol% amino groups deactivated) during the heat activation at
- the storage modulus readily increases immediately upon the start of heat activation.
- the lithium molybdate-catalyzed latent-reactive adhesive film prepared from dispersion 3, inventive example
- the memory module then increases significantly faster than the latent-reactive adhesive film without catalyst.
- the crosslinking reaction is initiated in the latent-reactive (pre) coatings, films, nonwovens or powders produced by the preparations according to the invention by supplying heat.
- the pre-coat, film, web or powder must either be at a temperature above the polymer's decrystallization temperature or at a temperature above the softening temperature of the deactivated aliphatic solid isocyanate (melting temperature or temperature)
- the (pre-) coating, the adhesive film, the adhesive non-woven or the adhesive powder can be applied to a surface of the substrates to be joined, placed or spread
- the latent-reactive coating, the latent-reactive film, the latent-reactive non-woven or the latent-reactive powder are prepared by short term heat activation e.g. heated in a heating channel, by means of IR rays or by irradiation with microwave waves to a temperature above the decrystallization temperature of the polymer or the softening temperature of the solid isocyanate. Immediately afterwards, the joining of the substrate surfaces takes place under pressure. The crosslinking reaction is only started by the short-term heat activation. The final properties of the cross-linked adhesive layer become 1-5
- the latent-reactive coating, the latent-reactive film, the latent-reactive non-woven or the latent-reactive powder are located between the substrates to be bonded.
- the substrates are pressed at a temperature above the decrystallization temperature of the polymer or above the softening temperature of the aliphatic solid isocyanate over a relatively long period of time. In this way, the final properties of the adhesive bond can be achieved immediately after the joining process.
- the advantage of this method of operation lies in the possibility of rapid further processing of the adhesive bond or in the possibility to carry out a quality test immediately after the joining process.
- the advantage of this mode of operation lies in the possibility of interconnecting the substrates in a short joining process.
- the final crosslinking then takes place in a second step, which can be separated from the first joining process, both spatially and temporally.
- Tamol ® NN 4501 (45% in water) protective colloid; Manufacturer: BASF AG, 67056 Ludwigshafen Borchigel ® ALA; Thickener; Manufacturer: Borchers GmbH, D-40765 Monheim.
- Emulsifier FD non-ionic emulsifier, manufacturer: Lanxess AG, Leverkusen
- Deionized water, emulsifiers, deactivating amine, thickener and solid isocyanate are submitted and with a dissolver disc at 2000 rpm within 15 min. mixed to a homogeneous suspension.
- the catalyst is first dissolved in deionized water. Then the emulsifiers, the deactivating amine, the thickener and the solid isocyanate are added and with a
- Dissolver disc at 2000 rpm within 15 min. mixed to a homogeneous suspension. - -
- Crosslinkers 1 and 3 contain 3 mol% of amino groups based on all available NCO groups of the IPDI trimer to deactivate the solid isocyanate.
- the deactivation of the IPDI trimer of formulations 2, 4, 5 and 6 was carried out with 7 mol% of amino groups relative to the available NCO groups of the IPDI trimer.
- the polymer dispersion are presented. With stirring, the formulations of the surface-deactivated solid isocyanates are added.
- Dispersion 1 (Comparative Dispercoll U 53 ® 100 polymer dispersion
- Dispersion 2 (Comparative Dispercoll U 53 ® 100 polymer dispersion
- Dispersion 1 and 2 are comparative examples without catalyst.
- Examples 3 to 6 are according to the invention.
- the composites were suspended in a heated oven heated to 80 ° C. and left to stand for 3 min. tempered. Thereafter, 2.5 kg of weights were attached to a PVC film and over a period of 5 min. the adhesive bond in the peel test (180 ° angle) at 80 0 C charged.
- the dispersions 2 (comparative) and 4 (invention) were stored in a freezer 24 hr. At -5 0 C.
- the polymer precipitated in the form of coarse solid particles.
- the formulation was warmed to room temperature and the precipitated polymer was filtered by filtration Serum separated. The polymer was then gently dried and ground in a jet mill with cooling to a particle size of d50 about 100 microns.
- the textile adhesives were first hung without weight load in the tempered to 6O 0 C heating cabinet and 30 min. tempered. Subsequently, the adhesive bond (180 ° peel test) were loaded with a 50g weight and another 30 min. left at 6O 0 C. At the end of the 30 minute test, the peeled distance [mm] was determined. This was followed by a temperature increase of 10 ° C. every 30 minutes. After the end of each temperature step, the peeled-off section was determined.
- the accelerated crosslinking of the latent-reactive powder with the lithium molybdate is here visible through the small Abtechnologylrange up to a temperature of 15O 0 C.
- the adhesive bond with the powder without Lithiummolybat is already completely separated at 100 0 C.
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesive Tapes (AREA)
Abstract
Description
Claims
Priority Applications (6)
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AT07856300T ATE532807T1 (de) | 2006-12-12 | 2007-11-29 | Klebstoffe |
EP20070856300 EP2099840B1 (de) | 2006-12-12 | 2007-11-29 | Klebstoffe |
BRPI0720278-4A2A BRPI0720278A2 (pt) | 2006-12-12 | 2007-11-29 | Adesivos |
JP2009540625A JP2010512436A (ja) | 2006-12-12 | 2007-11-29 | 接着剤 |
CN2007800459345A CN101652398B (zh) | 2006-12-12 | 2007-11-29 | 粘合剂 |
KR1020097014454A KR101500768B1 (ko) | 2006-12-12 | 2007-11-29 | 접착제 |
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DE102006058527.5 | 2006-12-12 | ||
DE102006058527A DE102006058527A1 (de) | 2006-12-12 | 2006-12-12 | Klebstoffe |
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WO2008071307A1 true WO2008071307A1 (de) | 2008-06-19 |
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PCT/EP2007/010345 WO2008071307A1 (de) | 2006-12-12 | 2007-11-29 | Klebstoffe |
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US (1) | US20080171208A1 (de) |
EP (1) | EP2099840B1 (de) |
JP (2) | JP2010512436A (de) |
KR (1) | KR101500768B1 (de) |
CN (1) | CN101652398B (de) |
AT (1) | ATE532807T1 (de) |
BR (1) | BRPI0720278A2 (de) |
DE (1) | DE102006058527A1 (de) |
RU (1) | RU2466149C2 (de) |
WO (1) | WO2008071307A1 (de) |
ZA (1) | ZA200904058B (de) |
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EP0922720A1 (de) * | 1997-12-11 | 1999-06-16 | Abend, Thomas | Verfahren zur Herstellung und Verwendung von lagerstabilen latentreaktiven Schichten oder Pulvern aus oberflächendesaktivierten festen Polyisocyanaten und Dispersionspolymeren mit funktionellen Gruppen |
EP1172390A1 (de) * | 2000-07-15 | 2002-01-16 | Jowat Lobers & Frank Gmbh & Co. Kg | Lagerstabile Isocyanatdispersionen |
WO2003016374A1 (de) * | 2001-08-16 | 2003-02-27 | Bayer Materialscience Ag | Einkomponentige isocyanatvernetzende zweiphasen-systeme |
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DE102004026118A1 (de) * | 2004-05-28 | 2005-12-15 | Bayer Materialscience Ag | Klebstoffe |
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2006
- 2006-12-12 DE DE102006058527A patent/DE102006058527A1/de not_active Withdrawn
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2007
- 2007-11-29 JP JP2009540625A patent/JP2010512436A/ja active Pending
- 2007-11-29 WO PCT/EP2007/010345 patent/WO2008071307A1/de active Application Filing
- 2007-11-29 RU RU2009126425/04A patent/RU2466149C2/ru not_active IP Right Cessation
- 2007-11-29 KR KR1020097014454A patent/KR101500768B1/ko active IP Right Grant
- 2007-11-29 CN CN2007800459345A patent/CN101652398B/zh active Active
- 2007-11-29 EP EP20070856300 patent/EP2099840B1/de active Active
- 2007-11-29 BR BRPI0720278-4A2A patent/BRPI0720278A2/pt not_active IP Right Cessation
- 2007-11-29 AT AT07856300T patent/ATE532807T1/de active
- 2007-12-10 US US12/001,158 patent/US20080171208A1/en not_active Abandoned
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2009
- 2009-06-10 ZA ZA200904058A patent/ZA200904058B/xx unknown
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2014
- 2014-08-21 JP JP2014168573A patent/JP5876548B2/ja not_active Expired - Fee Related
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EP0922720A1 (de) * | 1997-12-11 | 1999-06-16 | Abend, Thomas | Verfahren zur Herstellung und Verwendung von lagerstabilen latentreaktiven Schichten oder Pulvern aus oberflächendesaktivierten festen Polyisocyanaten und Dispersionspolymeren mit funktionellen Gruppen |
EP1172390A1 (de) * | 2000-07-15 | 2002-01-16 | Jowat Lobers & Frank Gmbh & Co. Kg | Lagerstabile Isocyanatdispersionen |
WO2003016374A1 (de) * | 2001-08-16 | 2003-02-27 | Bayer Materialscience Ag | Einkomponentige isocyanatvernetzende zweiphasen-systeme |
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Cited By (11)
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JP2012522094A (ja) * | 2009-03-31 | 2012-09-20 | シーカ・テクノロジー・アーゲー | 表面不活性化ポリイソシアネートを含む熱硬化性組成物又は熱活性化可能な組成物 |
JP2016053166A (ja) * | 2009-03-31 | 2016-04-14 | ジーカ テクノロジー アクチェンゲゼルシャフト | 表面不活性化ポリイソシアネートを含む熱硬化性組成物又は熱活性化可能 |
KR101753889B1 (ko) * | 2009-03-31 | 2017-07-04 | 시카 테크놀러지 아게 | 표면-불활성화 폴리이소시아네이트를 함유하는 열 경화성 또는 열-활성화 조성물 |
EP2244489A1 (de) | 2009-04-24 | 2010-10-27 | Bayer MaterialScience AG | Verfahren zur Herstellung eines elektromechanischen Wandlers |
WO2010121720A1 (de) | 2009-04-24 | 2010-10-28 | Bayer Materialscience Ag | Verfahren zur herstellung eines elektromechanischen wandlers |
WO2011015303A1 (de) | 2009-08-07 | 2011-02-10 | Bayer Materialscience Ag | Verfahren zur herstellung eines elektromechanischen wandlers |
EP2284919A1 (de) | 2009-08-07 | 2011-02-16 | Bayer MaterialScience AG | Verfahren zur Herstellung eines elektromechanischen Wandlers |
JP2013509468A (ja) * | 2009-10-29 | 2013-03-14 | バイエル・マテリアルサイエンス・アクチェンゲゼルシャフト | 結晶質または半結晶質ポリウレタンポリマーに基づく水性処方物 |
EP3027668B1 (de) | 2013-07-30 | 2019-09-04 | H. B. Fuller Company | Polyurethanhaftfolie |
EP3730528A1 (de) | 2019-04-24 | 2020-10-28 | Covestro Deutschland AG | Latent-reaktive klebstoffzubereitungen |
WO2020216680A1 (de) | 2019-04-24 | 2020-10-29 | Covestro Intellectual Property Gmbh & Co. Kg | Latent-reaktive klebstoffzubereitungen |
Also Published As
Publication number | Publication date |
---|---|
EP2099840A1 (de) | 2009-09-16 |
RU2009126425A (ru) | 2011-01-20 |
ZA200904058B (en) | 2010-08-25 |
DE102006058527A1 (de) | 2008-06-19 |
JP2015004067A (ja) | 2015-01-08 |
KR20090088949A (ko) | 2009-08-20 |
EP2099840B1 (de) | 2011-11-09 |
KR101500768B1 (ko) | 2015-03-09 |
CN101652398B (zh) | 2012-03-21 |
ATE532807T1 (de) | 2011-11-15 |
CN101652398A (zh) | 2010-02-17 |
JP5876548B2 (ja) | 2016-03-02 |
BRPI0720278A2 (pt) | 2014-01-28 |
JP2010512436A (ja) | 2010-04-22 |
US20080171208A1 (en) | 2008-07-17 |
RU2466149C2 (ru) | 2012-11-10 |
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