JP2000506195A - イソシアネート組成物、それらを利用する方法、コーティングを製造するためのそれらの利用、および得られたコーティング - Google Patents
イソシアネート組成物、それらを利用する方法、コーティングを製造するためのそれらの利用、および得られたコーティングInfo
- Publication number
- JP2000506195A JP2000506195A JP9530676A JP53067697A JP2000506195A JP 2000506195 A JP2000506195 A JP 2000506195A JP 9530676 A JP9530676 A JP 9530676A JP 53067697 A JP53067697 A JP 53067697A JP 2000506195 A JP2000506195 A JP 2000506195A
- Authority
- JP
- Japan
- Prior art keywords
- isocyanate
- group
- composition according
- carbon
- composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 101
- 239000012948 isocyanate Substances 0.000 title claims abstract description 49
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 45
- 238000000576 coating method Methods 0.000 title claims description 35
- 238000000034 method Methods 0.000 title claims description 21
- 125000000524 functional group Chemical group 0.000 claims abstract description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- -1 ethyleneoxy units Chemical group 0.000 claims abstract description 19
- 239000012634 fragment Substances 0.000 claims abstract description 16
- 125000000129 anionic group Chemical group 0.000 claims abstract description 15
- 239000002202 Polyethylene glycol Chemical group 0.000 claims abstract description 14
- 229920001223 polyethylene glycol Chemical group 0.000 claims abstract description 14
- 125000003827 glycol group Chemical group 0.000 claims abstract description 10
- 229920005862 polyol Polymers 0.000 claims description 34
- 150000003077 polyols Chemical class 0.000 claims description 34
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 31
- 239000011248 coating agent Substances 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 239000000839 emulsion Substances 0.000 claims description 20
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 19
- 238000001035 drying Methods 0.000 claims description 14
- 239000005056 polyisocyanate Substances 0.000 claims description 12
- 229920001228 polyisocyanate Polymers 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 11
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- 239000011574 phosphorus Substances 0.000 claims description 10
- 239000013638 trimer Substances 0.000 claims description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000008346 aqueous phase Substances 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000005977 Ethylene Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- 239000000049 pigment Substances 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 8
- 150000001768 cations Chemical class 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 150000001787 chalcogens Chemical group 0.000 claims description 5
- 230000001747 exhibiting effect Effects 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 3
- 230000001804 emulsifying effect Effects 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 229910052752 metalloid Inorganic materials 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 238000005507 spraying Methods 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims 6
- 150000007942 carboxylates Chemical group 0.000 claims 1
- COPLXRFZXQINJM-UHFFFAOYSA-N isocyanic acid;hydrate Chemical compound O.N=C=O COPLXRFZXQINJM-UHFFFAOYSA-N 0.000 claims 1
- 239000007764 o/w emulsion Substances 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000004816 latex Substances 0.000 description 14
- 229920000126 latex Polymers 0.000 description 14
- 239000002245 particle Substances 0.000 description 14
- 239000003973 paint Substances 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 13
- 239000002966 varnish Substances 0.000 description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
- 125000001183 hydrocarbyl group Chemical group 0.000 description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- 125000005442 diisocyanate group Chemical group 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 150000005690 diesters Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 150000001449 anionic compounds Chemical class 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- AVWRKZWQTYIKIY-UHFFFAOYSA-M urea-1-carboxylate Chemical group NC(=O)NC([O-])=O AVWRKZWQTYIKIY-UHFFFAOYSA-M 0.000 description 4
- 241001550224 Apha Species 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 150000001767 cationic compounds Chemical class 0.000 description 3
- 229910052798 chalcogen Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate group Chemical group [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229910001411 inorganic cation Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 241000282372 Panthera onca Species 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 229920006243 acrylic copolymer Polymers 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000009396 hybridization Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 150000002892 organic cations Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 150000003138 primary alcohols Chemical group 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-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
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- NHQYSNVBWHAWBR-UHFFFAOYSA-N C(C)N(CC)CC.C(CCCCCCCCCCC)OS(=O)(=O)C1=CC=CC=C1 Chemical compound C(C)N(CC)CC.C(CCCCCCCCCCC)OS(=O)(=O)C1=CC=CC=C1 NHQYSNVBWHAWBR-UHFFFAOYSA-N 0.000 description 1
- 240000008886 Ceratonia siliqua Species 0.000 description 1
- 235000013912 Ceratonia siliqua Nutrition 0.000 description 1
- 241000921896 Charybdis <crab> Species 0.000 description 1
- 244000007835 Cyamopsis tetragonoloba Species 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 241000519695 Ilex integra Species 0.000 description 1
- 229920005692 JONCRYL® Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 241000238102 Scylla Species 0.000 description 1
- 201000001880 Sexual dysfunction Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- WFWLQNSHRPWKFK-UHFFFAOYSA-N Tegafur Chemical compound O=C1NC(=O)C(F)=CN1C1OCCC1 WFWLQNSHRPWKFK-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000005600 alkyl phosphonate group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000004292 cyclic ethers Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229920000591 gum Polymers 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 150000002506 iron compounds Chemical class 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 150000002738 metalloids Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 230000003606 oligomerizing effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003003 phosphines Chemical group 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229940048084 pyrophosphate Drugs 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic 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
- C08G18/703—Isocyanates or isothiocyanates transformed in a latent form by physical means
- C08G18/705—Dispersions of isocyanates or isothiocyanates in a liquid medium
- C08G18/706—Dispersions of isocyanates or isothiocyanates in a liquid medium the liquid medium being water
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/18—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/14—Derivatives of isocyanic acid containing at least two isocyanate groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3878—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus
- C08G18/3882—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus having phosphorus bound to oxygen only
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
- C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—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
- C08G18/70—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
-
- 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
- C09D175/04—Polyurethanes
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- Chemical & Material Sciences (AREA)
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- General Preparation And Processing Of Foods (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.アニオン性官能基と、好ましくは少なくとも1つの、より好ましくは少な くとも5つのエチレンオキシ単位のポリエチレングリコール鎖断片とを含有する 少なくとも1種の化合物を含むことを特徴とする、好ましくは完全にはマスクさ れていない、1種または2種以上のイソシアネートをベースとする組成物。 2.前記化合物が前記アニオン性官能基により形成された親水性部分と、前記 ポリエチレングリコール鎖断片と、炭化水素をベースとする親油性部分とを含有 することを特徴とする、請求項1に記載の組成物。 3.前記親油性部分がアルキル基およびアリール基から選択されることを特徴 とする、請求項1または2に記載の組成物。 4.前記化合物が、下記式Iに相当することを特徴とする、請求項1〜3のい ずれか一項に記載の組成物。 式中、 qは0または1であり、 pは1および2の間の整数であり(閉じた間隔、すなわち、限界を含む)、 mは0または1および2の間の整数であり(閉じた間隔、すなわち、限界を含 む)、 XおよびX’は同一であるか、あるいは異なり、最大2個の炭素鎖の結合を含 有するアームであり、 sは1〜30、好ましくは5〜25、より好ましくは9〜20の間から選択さ れる整数であり(閉じた間隔、すなわち、限界を含む)、 nは1〜30、好ましくは5〜25、より好ましくは9〜20の間から選択さ れる整数であり(閉じた間隔、すなわち、限界を含む)、 Eは炭素および少なくともリンの原子族に等しくかつ第VB族またはカルコゲ ンに属する原子族のメタロイド元素から選択される元素であり、 R1およびR2は同一であるか、あるいは異り、炭化水素基であり、好ましくは 置換されていてもよいアリールおよびアルキルから選択される炭化水素基である 。 5.対カチオンがアミン、好ましくは第三級アミンであることを特徴とする、 請求項1〜4のいずれか一項に記載の組成物。 6.好ましくは潜伏性触媒をさらに含むことを特徴とする、請求項1〜5のい ずれか一項に記載の組成物。 7.下記の特性を示すポリオールをさらに含むことを特徴とする、請求項1〜 6のいずれか一項に記載の組成物。 8.前記ポリオールがナノラテックスであることを特徴とする、請求項7に記 載の組成物。 9.前記ポリオールが下記の特性を示すナノラテックスであることを特徴とす る、請求項7または8に記載の組成物: 15〜60nmのd50; 0.5〜5質量%のカルボキレート官能基; 1〜3%のオール官能基; 25〜40%の固形分; 1マイクロメートルより小さいd80。 10.界面活性剤/イソシアネートの質量比が20%より小さく、好ましくは 4/10であることを特徴とする、請求項1〜9のいずれか一項に記載の組成物 。 11.前記組成物が水中のイソシアネートのエマルジョンであり、好ましくは 最大3マイクロメートル、より好ましくは1マイクロメートルに等しいd50、よ り好ましくはd80を示すことを特徴とする、請求項10に記載の組成物。 12.10〜70%の水分を有する水中油型エマルジョンを構成することを特 徴とする、請求項1〜11のいずれか一項に記載の組成物。 13.水中のイソシアネート+乳化剤+アルコールの含量が30〜70%であ ることを特徴とする、請求項1〜12のいずれか一項に記載の組成物。 14.イソシアネートをポリオール+水の混合物に添加することを含むことを 特徴とする、イソシアネート13を乳化する方法。 15.撹拌をマニュアルまたは機械的に行うことを特徴とする、請求項14に 記載の方法。 16.50℃より低い周囲温度においてにおいて実施することを特徴とする、 請求項14または15に記載の方法。 17.水性相のpHを3より高い値、好ましくは4に調節することを特徴とす る、請求項14〜16のいずれか一項に記載の方法。 18.イソシアネートの添加前に、1種または2種以上のポリオールの中に顔 料を分散させることを特徴とする、請求項14〜17のいずれか一項に記載の方 法。 19.乾燥状態で10〜150マイクロメートル、好ましくは20〜80マイ クロメートル、より好ましくは30〜40マイクロメートル、湿潤状態で60〜 150マイクロメートル、の層を適用す ることからなることを特徴とする、コーティング18を製造する方法。 20.20℃〜50℃において15分〜3時間乾燥することを含むことを特徴 とする、請求項19に記載の方法。 21.溶媒の存在において乾燥を実施して水の除去を促進することを特徴とす る、請求項19〜20のいずれか一項に記載の方法。 22.コーティングをスプレーによるか、あるいはねじ込みロッドのアプリケ ーターにより適用することを特徴とする、請求項19〜21のいずれか一項に記 載の方法。 23.式: (式中、 Eは周期表[Bulletin de la Soci t Chimiqu e de France January 1966 No.1に対する補遺] の第VA族の元素、好ましくはリンであり、したがって、 であり、 Isoはイソシアネートまたはポリイソシアネートの残基(1つのイソシアネ ート基を除去した後の)であり、 R10は負の電荷または炭化水素残基(すなわち、水素原子および炭素原子を含 有する)であり、その結合点(すなわち、解放結合を有する原子)は炭素であり 、R11は、 − 負の電荷; − 式II: の基; から選択され、 R'10は炭化水素残基(R10と同一であるか、あるいは異なる)および負の電 荷から選択され、その結合点(すなわち、解放結合を有する原子)は炭素であり 、1またはそれより多いR'11は炭化水素残基から選択され、その結合点(すな わち、解放結合を有する原子)は炭素であり、これはR10およびR'11と同一で あるか、あるいは異なる)および負の電荷から選択される) の化合物。 24.Isoがトリマー(イソシアヌレート)またはビウレット(少なくとも 1つのモノマーはエチレン鎖配列を介してそのイソシアネート官能基を有する) の残基であることを特徴とする、請求項23に記載の化合物。 25.Isoがトリマー(イソシアヌレート)またはビウレット(モノマーは エチレン鎖配列を介してそのイソシアネート官能基を有する)の残基であること を特徴とする、請求項23または24に記載の化合物。 26.エチレン鎖配列を介してそのイソシアネート官能基を有する1またはそ れより多いモノマーがポリメチレンジイソシアネート、好ましくはヘキサメチレ ンジイソシアネートであることを特徴とする、請求項24または25に記載の化 合物。 27.Isoかヘキサメチレンジイソシアネートのトリマー(イソシアヌレー ト)の残基であることを特徴とする、請求項23または25に記載の化合物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9602710A FR2745577B1 (fr) | 1996-02-29 | 1996-02-29 | Compositions a base d'isocyanate, leur procede d'utilisation leur utilisation pour realiser des revetements et revetement ainsi obtenu |
FR96/02710 | 1996-02-29 | ||
PCT/FR1997/000359 WO1997031960A1 (fr) | 1996-02-29 | 1997-02-28 | Compositions a base d'isocyanate, leur procede d'utilisation, leur utilisation pour realiser des revetements et revetements ainsi obtenus |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006249975A Division JP2007016047A (ja) | 1996-02-29 | 2006-09-14 | 界面活性剤特性を有するイソシアネート化合物 |
Publications (3)
Publication Number | Publication Date |
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JP2000506195A true JP2000506195A (ja) | 2000-05-23 |
JP2000506195A5 JP2000506195A5 (ja) | 2004-11-25 |
JP4138879B2 JP4138879B2 (ja) | 2008-08-27 |
Family
ID=9489839
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JP53067697A Expired - Lifetime JP4138879B2 (ja) | 1996-02-29 | 1997-02-28 | イソシアネート組成物、それらを利用する方法、コーティングを製造するためのそれらの利用、および得られたコーティング |
JP2006249975A Pending JP2007016047A (ja) | 1996-02-29 | 2006-09-14 | 界面活性剤特性を有するイソシアネート化合物 |
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JP2006249975A Pending JP2007016047A (ja) | 1996-02-29 | 2006-09-14 | 界面活性剤特性を有するイソシアネート化合物 |
Country Status (15)
Country | Link |
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EP (2) | EP1524281A2 (ja) |
JP (2) | JP4138879B2 (ja) |
KR (1) | KR100513077B1 (ja) |
CN (2) | CN1273445C (ja) |
AT (1) | ATE294826T1 (ja) |
AU (1) | AU1930397A (ja) |
BR (1) | BR9707712A (ja) |
CA (1) | CA2247182A1 (ja) |
DE (2) | DE69733171T2 (ja) |
ES (1) | ES2140361T3 (ja) |
FR (1) | FR2745577B1 (ja) |
HU (1) | HUP9900936A3 (ja) |
MX (1) | MX229227B (ja) |
WO (1) | WO1997031960A1 (ja) |
ZA (1) | ZA971768B (ja) |
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-
1996
- 1996-02-29 FR FR9602710A patent/FR2745577B1/fr not_active Expired - Fee Related
-
1997
- 1997-02-28 BR BR9707712A patent/BR9707712A/pt not_active IP Right Cessation
- 1997-02-28 ES ES97907149T patent/ES2140361T3/es not_active Expired - Lifetime
- 1997-02-28 DE DE69733171T patent/DE69733171T2/de not_active Expired - Lifetime
- 1997-02-28 DE DE0815153T patent/DE815153T1/de active Pending
- 1997-02-28 AU AU19303/97A patent/AU1930397A/en not_active Abandoned
- 1997-02-28 EP EP05001315A patent/EP1524281A2/fr not_active Withdrawn
- 1997-02-28 EP EP97907149A patent/EP0815153B1/fr not_active Expired - Lifetime
- 1997-02-28 HU HU9900936A patent/HUP9900936A3/hu unknown
- 1997-02-28 CA CA002247182A patent/CA2247182A1/fr not_active Abandoned
- 1997-02-28 KR KR1019980706749A patent/KR100513077B1/ko active IP Right Grant
- 1997-02-28 ZA ZA971768A patent/ZA971768B/xx unknown
- 1997-02-28 WO PCT/FR1997/000359 patent/WO1997031960A1/fr active IP Right Grant
- 1997-02-28 AT AT97907149T patent/ATE294826T1/de not_active IP Right Cessation
- 1997-02-28 CN CNB031041051A patent/CN1273445C/zh not_active Expired - Lifetime
- 1997-02-28 JP JP53067697A patent/JP4138879B2/ja not_active Expired - Lifetime
- 1997-02-28 CN CNB971935599A patent/CN1152073C/zh not_active Expired - Lifetime
-
1998
- 1998-08-27 MX MX9806970A patent/MX229227B/es active IP Right Grant
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2006
- 2006-09-14 JP JP2006249975A patent/JP2007016047A/ja active Pending
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2004509189A (ja) * | 2000-09-18 | 2004-03-25 | ロディア・シミ | 木製基材に化学物質による攻撃に対する高い耐性を提供する方法 |
JP2006522850A (ja) * | 2003-04-08 | 2006-10-05 | ロディア・シミ | イソシアネートをベースとする組成物、接着剤の製造のためのその使用方法、及び得られる芳香族接着性ジョイント |
KR101268988B1 (ko) | 2004-12-21 | 2013-05-31 | 벤코렉스 프랑스 | 개선된 내-충격성을 갖는 폴리이소시아네이트 조성물 |
JP2008524422A (ja) * | 2004-12-21 | 2008-07-10 | ロディア・シミ | 改良された耐衝撃性を有するポリイソシアネート組成物 |
JP2008529973A (ja) * | 2004-12-23 | 2008-08-07 | ロディア・シミ | 良好な混合特性を示すイソシアネート組成物、及びイソシアネート組成物の助剤、特に混合助剤としてのシリル化誘導体の使用 |
JP2007084801A (ja) * | 2005-08-22 | 2007-04-05 | Kansai Paint Co Ltd | 水性2液型クリヤ塗料組成物及び複層塗膜形成方法 |
WO2008050756A1 (fr) * | 2006-10-23 | 2008-05-02 | Kansai Paint Co., Ltd. | Composition de revêtement transparente aqueuse à deux composants et procédé destiné à former un film de revêtement de finition multicouche |
US8563636B2 (en) | 2006-10-23 | 2013-10-22 | Kansai Paint Co., Ltd. | Aqueous two-package type clear coating composition and process for the formation of multilayer finish coating film |
JP5424643B2 (ja) * | 2006-10-23 | 2014-02-26 | 関西ペイント株式会社 | 水性2液型クリヤ塗料組成物及び上塗り複層塗膜形成方法 |
WO2016121238A1 (ja) * | 2015-01-29 | 2016-08-04 | 関西ペイント株式会社 | 複層塗膜形成方法 |
JPWO2016121238A1 (ja) * | 2015-01-29 | 2017-11-09 | 関西ペイント株式会社 | 複層塗膜形成方法 |
US10639672B2 (en) | 2015-01-29 | 2020-05-05 | Kansai Paint Co., Ltd. | Method for forming multilayer coating film |
WO2016121239A1 (ja) * | 2015-01-30 | 2016-08-04 | 関西ペイント株式会社 | 複層塗膜形成方法 |
JPWO2016121239A1 (ja) * | 2015-01-30 | 2017-11-09 | 関西ペイント株式会社 | 複層塗膜形成方法 |
US10508212B2 (en) | 2015-01-30 | 2019-12-17 | Kansai Paint Co., Ltd. | Method for forming multilayer coating film |
Also Published As
Publication number | Publication date |
---|---|
CN1215415A (zh) | 1999-04-28 |
EP0815153B1 (fr) | 2005-05-04 |
KR19990087340A (ko) | 1999-12-27 |
HUP9900936A3 (en) | 1999-11-29 |
BR9707712A (pt) | 1999-04-06 |
ATE294826T1 (de) | 2005-05-15 |
EP1524281A2 (fr) | 2005-04-20 |
FR2745577A1 (fr) | 1997-09-05 |
ES2140361T1 (es) | 2000-03-01 |
DE815153T1 (de) | 2000-04-06 |
JP4138879B2 (ja) | 2008-08-27 |
CN1515638A (zh) | 2004-07-28 |
CA2247182A1 (fr) | 1997-09-04 |
FR2745577B1 (fr) | 2004-09-24 |
CN1152073C (zh) | 2004-06-02 |
EP0815153A1 (fr) | 1998-01-07 |
DE69733171T2 (de) | 2006-02-16 |
MX229227B (es) | 2005-07-19 |
KR100513077B1 (ko) | 2006-02-28 |
CN1273445C (zh) | 2006-09-06 |
ZA971768B (en) | 1998-08-28 |
ES2140361T3 (es) | 2005-11-01 |
AU1930397A (en) | 1997-09-16 |
HUP9900936A1 (hu) | 1999-07-28 |
JP2007016047A (ja) | 2007-01-25 |
DE69733171D1 (de) | 2005-06-09 |
WO1997031960A1 (fr) | 1997-09-04 |
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