HRP950457A2 - Polyurethane compositions having a low content of monomer diisocyanates - Google Patents
Polyurethane compositions having a low content of monomer diisocyanates Download PDFInfo
- Publication number
- HRP950457A2 HRP950457A2 HRP4441770.5A HRP950457A HRP950457A2 HR P950457 A2 HRP950457 A2 HR P950457A2 HR P950457 A HRP950457 A HR P950457A HR P950457 A2 HRP950457 A2 HR P950457A2
- Authority
- HR
- Croatia
- Prior art keywords
- mass
- formulation
- prepolymer
- diisocyanate
- formulation according
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 76
- 125000005442 diisocyanate group Chemical group 0.000 title claims description 33
- 239000000178 monomer Substances 0.000 title claims description 18
- 229920002635 polyurethane Polymers 0.000 title description 18
- 239000004814 polyurethane Substances 0.000 title description 18
- 238000009472 formulation Methods 0.000 claims description 60
- 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 37
- 239000000853 adhesive Substances 0.000 claims description 35
- 230000001070 adhesive effect Effects 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 34
- 239000005056 polyisocyanate Substances 0.000 claims description 30
- 229920001228 polyisocyanate Polymers 0.000 claims description 30
- 229920005862 polyol Polymers 0.000 claims description 28
- 239000012948 isocyanate Substances 0.000 claims description 27
- 150000002513 isocyanates Chemical class 0.000 claims description 27
- 238000004519 manufacturing process Methods 0.000 claims description 27
- 150000003077 polyols Chemical class 0.000 claims description 27
- 238000007789 sealing Methods 0.000 claims description 27
- 239000006260 foam Substances 0.000 claims description 23
- 239000004831 Hot glue Substances 0.000 claims description 21
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 20
- 229920003023 plastic Polymers 0.000 claims description 20
- 239000004033 plastic Substances 0.000 claims description 20
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 19
- 238000004026 adhesive bonding Methods 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 239000003381 stabilizer Substances 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 9
- 150000002009 diols Chemical class 0.000 claims description 9
- 239000011888 foil Substances 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 8
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 7
- 239000011248 coating agent Substances 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 239000004848 polyfunctional curative Substances 0.000 claims description 5
- 239000003380 propellant Substances 0.000 claims description 5
- 238000005829 trimerization reaction Methods 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 4
- 125000003700 epoxy group Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 3
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 3
- 239000000123 paper Substances 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 0.000 claims description 3
- 150000004072 triols Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 229920000768 polyamine Polymers 0.000 claims description 2
- 229920005906 polyester polyol Polymers 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims 3
- 239000005058 Isophorone diisocyanate Substances 0.000 claims 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
- 239000004744 fabric Substances 0.000 claims 1
- 150000003141 primary amines Chemical class 0.000 claims 1
- 239000011814 protection agent Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- -1 benzyl alcohol, fatty alcohols Chemical class 0.000 description 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 10
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- 230000002349 favourable effect Effects 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 239000003292 glue Substances 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 229910052718 tin Inorganic materials 0.000 description 6
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 5
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 5
- 239000004800 polyvinyl chloride Substances 0.000 description 5
- 229920000915 polyvinyl chloride Polymers 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000002023 wood Substances 0.000 description 5
- ZMSQJSMSLXVTKN-UHFFFAOYSA-N 4-[2-(2-morpholin-4-ylethoxy)ethyl]morpholine Chemical compound C1COCCN1CCOCCN1CCOCC1 ZMSQJSMSLXVTKN-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000006229 carbon black Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000010276 construction Methods 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- 229920005830 Polyurethane Foam Polymers 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 239000012973 diazabicyclooctane Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000011496 polyurethane foam Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 description 2
- HUXPJAYTCUJDJY-UHFFFAOYSA-N 1-(2-amino-2-methylpropoxy)-2-methylpropan-2-amine Chemical compound CC(C)(N)COCC(C)(C)N HUXPJAYTCUJDJY-UHFFFAOYSA-N 0.000 description 2
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 2
- JTAXUBKTCAOMTN-UHFFFAOYSA-N Abietinol Natural products CC(C)C1=CC2C=CC3C(C)(CO)CCCC3(C)C2CC1 JTAXUBKTCAOMTN-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000012963 UV stabilizer Substances 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- GQRUHVMVWNKUFW-LWYYNNOASA-N abieta-7,13-dien-18-ol Chemical compound OC[C@]1(C)CCC[C@]2(C)[C@@H](CCC(C(C)C)=C3)C3=CC[C@H]21 GQRUHVMVWNKUFW-LWYYNNOASA-N 0.000 description 2
- 229930001565 abietol Natural products 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 235000011837 pasties Nutrition 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 150000003606 tin compounds Chemical class 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 229940113165 trimethylolpropane Drugs 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 1
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- SSUJUUNLZQVZMO-UHFFFAOYSA-N 1,2,3,4,8,9,10,10a-octahydropyrimido[1,2-a]azepine Chemical compound C1CCC=CN2CCCNC21 SSUJUUNLZQVZMO-UHFFFAOYSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- KLCNDZKZXMQNBO-UHFFFAOYSA-N 1,2-bis[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1CC1=CC=C(N=C=O)C=C1 KLCNDZKZXMQNBO-UHFFFAOYSA-N 0.000 description 1
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
- MONBXKAJLMCVCS-UHFFFAOYSA-N 1-isocyanato-2,3-bis[(2-isocyanatophenyl)methyl]benzene Chemical compound O=C=NC1=CC=CC=C1CC1=CC=CC(N=C=O)=C1CC1=CC=CC=C1N=C=O MONBXKAJLMCVCS-UHFFFAOYSA-N 0.000 description 1
- PEWXEXAYLPQJBI-UHFFFAOYSA-N 1-isocyanato-2,3-bis[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC(N=C=O)=C1CC1=CC=C(N=C=O)C=C1 PEWXEXAYLPQJBI-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- AXFVIWBTKYFOCY-UHFFFAOYSA-N 1-n,1-n,3-n,3-n-tetramethylbutane-1,3-diamine Chemical compound CN(C)C(C)CCN(C)C AXFVIWBTKYFOCY-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- BNOSAGKHYAMZGF-UHFFFAOYSA-N 2-isocyanato-1,3-bis[(2-isocyanatophenyl)methyl]benzene Chemical compound O=C=NC1=CC=CC=C1CC1=CC=CC(CC=2C(=CC=CC=2)N=C=O)=C1N=C=O BNOSAGKHYAMZGF-UHFFFAOYSA-N 0.000 description 1
- KIBAANMHKKFBLT-UHFFFAOYSA-N 2-isocyanato-1,4-bis[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC(C=C1N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 KIBAANMHKKFBLT-UHFFFAOYSA-N 0.000 description 1
- OIJOSYKNWPGOOP-UHFFFAOYSA-N 2-isocyanato-4-[(3-isocyanatophenyl)methyl]-1-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC(C(=C1)N=C=O)=CC=C1CC1=CC=CC(N=C=O)=C1 OIJOSYKNWPGOOP-UHFFFAOYSA-N 0.000 description 1
- HEBTZZBBPUFAFE-UHFFFAOYSA-N 2-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=CC=C1S(=O)(=O)N=C=O HEBTZZBBPUFAFE-UHFFFAOYSA-N 0.000 description 1
- WMRCTEPOPAZMMN-UHFFFAOYSA-N 2-undecylpropanedioic acid Chemical compound CCCCCCCCCCCC(C(O)=O)C(O)=O WMRCTEPOPAZMMN-UHFFFAOYSA-N 0.000 description 1
- QYDIWKPIGAEUEG-UHFFFAOYSA-N 4-isocyanato-1,2-bis[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1CC1=CC=C(N=C=O)C=C1 QYDIWKPIGAEUEG-UHFFFAOYSA-N 0.000 description 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 241001253206 Andrias Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
-
- 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
-
- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
- C08G18/2825—Alkanols, cycloalkanols or arylalkanols including terpenealcohols having at least 6 carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
- C08G18/289—Compounds containing at least one heteroatom other than oxygen or nitrogen containing silicon
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2170/00—Compositions for adhesives
- C08G2170/20—Compositions for hot melt adhesives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/26—Natural polymers, natural resins or derivatives thereof according to C08L1/00 - C08L5/00, C08L89/00, C08L93/00, C08L97/00 or C08L99/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Sealing Material Composition (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4429679A DE4429679A1 (de) | 1994-08-22 | 1994-08-22 | Reaktiver Polyurethan-Schmelzklebstoff |
| DE19944440322 DE4440322A1 (de) | 1994-11-11 | 1994-11-11 | Reaktive Polyurethan-Kleb-/Dichtmasse |
| DE19944441190 DE4441190A1 (de) | 1994-11-18 | 1994-11-18 | Primer für lackierte Oberflächen |
| DE19944441570 DE4441570A1 (de) | 1994-11-23 | 1994-11-23 | Schaumkunststoff aus Einweg-Druckbehältern |
| DE19944441770 DE4441770A1 (de) | 1994-11-24 | 1994-11-24 | Kaschierklebstoffe auf Basis von Polyurethanen mit niedrigem Gehalt an monomeren Diisocyanaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP950457A2 true HRP950457A2 (en) | 1997-10-31 |
Family
ID=27511762
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP4441770.5A HRP950457A2 (en) | 1994-08-22 | 1995-08-21 | Polyurethane compositions having a low content of monomer diisocyanates |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5880167A (no) |
| EP (1) | EP0777695B2 (no) |
| JP (1) | JPH10504350A (no) |
| KR (1) | KR970705593A (no) |
| CN (1) | CN1155288A (no) |
| AT (1) | ATE174042T1 (no) |
| AU (1) | AU3345795A (no) |
| BR (1) | BR9508745A (no) |
| CA (1) | CA2198388A1 (no) |
| CZ (1) | CZ53197A3 (no) |
| DE (1) | DE59504433D1 (no) |
| DK (1) | DK0777695T4 (no) |
| ES (1) | ES2125651T5 (no) |
| FI (1) | FI970752A0 (no) |
| HR (1) | HRP950457A2 (no) |
| HU (1) | HUT77802A (no) |
| MX (1) | MX9701338A (no) |
| NO (1) | NO970238L (no) |
| PL (1) | PL318143A1 (no) |
| SK (1) | SK22797A3 (no) |
| WO (1) | WO1996006124A1 (no) |
| ZA (1) | ZA956985B (no) |
Families Citing this family (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19739191A1 (de) * | 1997-09-08 | 1999-03-11 | Henkel Kgaa | Verwendung Schaum-freier Zusammensetzungen mit einem Gehalt an Polyurethanen zur Herstellung von Gießharzen und Beschichtungsmassen |
| CA2311712C (en) † | 1997-12-01 | 2010-06-08 | Henkel Kommanditgesellschaft Auf Aktien | Modified polyurethane hotmelt adhesive |
| US5817860A (en) * | 1998-03-20 | 1998-10-06 | Essex Specialty Products, Inc. | Polyurethane prepolymer compositions, foams made therefrom and methods of making each thereof |
| US6221978B1 (en) | 1998-04-09 | 2001-04-24 | Henkel Corporation | Moisture curable hot melt adhesive and method for bonding substrates using same |
| DE60019866T2 (de) | 1999-10-08 | 2005-10-06 | Mitsui Takeda Chemicals, Inc. | Lösemittelfreie härtbare Zweikomponentklebstoffzusammensetzung |
| GB0002175D0 (en) * | 2000-01-31 | 2000-03-22 | Baxenden Chem Ltd | Low monomer foam |
| EP1311573B1 (en) * | 2000-08-08 | 2010-04-14 | Dow Global Technologies Inc. | Polyurethane foam composition |
| DE10048059A1 (de) * | 2000-09-28 | 2002-04-18 | Henkel Kgaa | Klebstoff mit Barriereeigenschaften |
| UA77951C2 (en) * | 2000-11-29 | 2007-02-15 | Laminate for packaging of food and method for its formation (variants) | |
| DE10062415A1 (de) * | 2000-12-14 | 2002-06-20 | Bayer Ag | Holzklebstoffe |
| JP2002249745A (ja) * | 2001-02-27 | 2002-09-06 | Mitsui Takeda Chemicals Inc | ２液硬化型無溶剤系接着剤組成物 |
| GB0108061D0 (en) * | 2001-03-30 | 2001-05-23 | Baxenden Chem | Low monomer one component foam |
| US6866743B2 (en) * | 2001-04-12 | 2005-03-15 | Air Products And Chemicals, Inc. | Controlled structure polyurethane prepolymers for polyurethane structural adhesives |
| US6619009B2 (en) | 2001-04-30 | 2003-09-16 | Orbseal Llc | Reinforcement for expandable compositions and methods for using the reinforcement |
| MXPA03010562A (es) * | 2001-05-21 | 2004-03-02 | Huntsman Intenat Llc | Poliuretano elastomerico muy blando. |
| DE10229519A1 (de) * | 2001-07-10 | 2003-01-30 | Henkel Kgaa | Reaktive Polyurethane mit einem geringen Gehalt an monomeren Diisocyanaten |
| WO2003022546A1 (de) * | 2001-09-05 | 2003-03-20 | Jowat Ag | Verkleben von kunststoffextrudaten mit werkstoffoberflächen |
| US20030092848A1 (en) * | 2001-09-11 | 2003-05-15 | Ashok Sengupta | Sprayable liner for supporting the rock surface of a mine |
| US6664414B2 (en) * | 2001-09-11 | 2003-12-16 | 3M Innovative Properties Company | Process for reducing residual isocyanate |
| DE10150722A1 (de) | 2001-10-13 | 2003-04-30 | Henkel Kgaa | Reaktive Polyurethan-Zusammensetzungen mit niedrigem Restmonomergehalt |
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| GB2137638A (en) * | 1983-04-05 | 1984-10-10 | Bostik Ltd | Adhesive compositions |
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| ZA883499B (no) * | 1987-05-26 | 1988-11-28 | ||
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| DE3911784A1 (de) * | 1989-04-11 | 1990-10-18 | Peter Buesgen | Lagerstabile einkomponenten-polyurethanschaummischung |
| GB8908495D0 (en) * | 1989-04-14 | 1989-06-01 | Ici Plc | Polyisocyanate compositions |
| DE4025843A1 (de) * | 1990-08-16 | 1992-02-20 | Peter Buesgen | Lagerstabile einkomponenten-mischung zur herstellung von polyurethanschaum |
| DE4134302A1 (de) * | 1991-10-17 | 1993-04-22 | Basf Lacke & Farben | Hitzehaertbare ueberzugsmittel fuer die kathodische elektrotauchlackierung |
| US5461091A (en) * | 1991-10-17 | 1995-10-24 | Basf Aktiengesellschaft | Heat curable cathodic electrocoating composition |
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| AU691484B2 (en) * | 1993-02-10 | 1998-05-21 | Rathor Ag | Prepolymer composition for insulating foams |
-
1995
- 1995-08-14 AT AT95929868T patent/ATE174042T1/de not_active IP Right Cessation
- 1995-08-14 CA CA002198388A patent/CA2198388A1/en not_active Abandoned
- 1995-08-14 EP EP95929868A patent/EP0777695B2/de not_active Expired - Lifetime
- 1995-08-14 US US08/793,024 patent/US5880167A/en not_active Expired - Fee Related
- 1995-08-14 CZ CZ97531A patent/CZ53197A3/cs unknown
- 1995-08-14 AU AU33457/95A patent/AU3345795A/en not_active Abandoned
- 1995-08-14 DE DE59504433T patent/DE59504433D1/de not_active Expired - Fee Related
- 1995-08-14 ES ES95929868T patent/ES2125651T5/es not_active Expired - Lifetime
- 1995-08-14 CN CN95194637A patent/CN1155288A/zh active Pending
- 1995-08-14 BR BR9508745A patent/BR9508745A/pt not_active Application Discontinuation
- 1995-08-14 KR KR1019970701138A patent/KR970705593A/ko not_active Application Discontinuation
- 1995-08-14 HU HU9800496A patent/HUT77802A/hu unknown
- 1995-08-14 DK DK95929868T patent/DK0777695T4/da active
- 1995-08-14 PL PL95318143A patent/PL318143A1/xx unknown
- 1995-08-14 SK SK227-97A patent/SK22797A3/sk unknown
- 1995-08-14 JP JP8507760A patent/JPH10504350A/ja active Pending
- 1995-08-14 MX MX9701338A patent/MX9701338A/es not_active Application Discontinuation
- 1995-08-14 WO PCT/EP1995/003216 patent/WO1996006124A1/de not_active Application Discontinuation
- 1995-08-21 HR HRP4441770.5A patent/HRP950457A2/hr not_active Application Discontinuation
- 1995-08-21 ZA ZA956985A patent/ZA956985B/xx unknown
-
1997
- 1997-01-20 NO NO970238A patent/NO970238L/no unknown
- 1997-02-21 FI FI970752A patent/FI970752A0/fi not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| HUT77802A (hu) | 1998-08-28 |
| KR970705593A (ko) | 1997-10-09 |
| CN1155288A (zh) | 1997-07-23 |
| EP0777695B1 (de) | 1998-12-02 |
| NO970238D0 (no) | 1997-01-20 |
| MX9701338A (es) | 1997-05-31 |
| WO1996006124A1 (de) | 1996-02-29 |
| PL318143A1 (en) | 1997-05-12 |
| SK22797A3 (en) | 1997-09-10 |
| EP0777695A1 (de) | 1997-06-11 |
| CZ53197A3 (en) | 1997-10-15 |
| FI970752A (fi) | 1997-02-21 |
| ATE174042T1 (de) | 1998-12-15 |
| JPH10504350A (ja) | 1998-04-28 |
| DK0777695T4 (da) | 2004-07-12 |
| ZA956985B (en) | 1996-06-24 |
| NO970238L (no) | 1997-01-20 |
| DE59504433D1 (de) | 1999-01-14 |
| AU3345795A (en) | 1996-03-14 |
| BR9508745A (pt) | 1997-09-30 |
| EP0777695B2 (de) | 2004-03-17 |
| FI970752A0 (fi) | 1997-02-21 |
| ES2125651T5 (es) | 2004-11-01 |
| ES2125651T3 (es) | 1999-03-01 |
| US5880167A (en) | 1999-03-09 |
| CA2198388A1 (en) | 1996-02-29 |
| DK0777695T3 (da) | 1999-08-16 |
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