JP3946332B2 - コンクリート添加剤としての非イオン型の水分散性ポリイソシアネートの使用 - Google Patents
コンクリート添加剤としての非イオン型の水分散性ポリイソシアネートの使用 Download PDFInfo
- Publication number
- JP3946332B2 JP3946332B2 JP36481697A JP36481697A JP3946332B2 JP 3946332 B2 JP3946332 B2 JP 3946332B2 JP 36481697 A JP36481697 A JP 36481697A JP 36481697 A JP36481697 A JP 36481697A JP 3946332 B2 JP3946332 B2 JP 3946332B2
- Authority
- JP
- Japan
- Prior art keywords
- water
- weight
- polyisocyanate
- average
- ethylene oxide
- 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.)
- Expired - Fee Related
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- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 82
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 82
- 239000004567 concrete Substances 0.000 title claims abstract description 52
- 239000000654 additive Substances 0.000 title claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 54
- 229920000570 polyether Polymers 0.000 claims abstract description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 37
- 239000004570 mortar (masonry) Substances 0.000 claims abstract description 36
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 32
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000011230 binding agent Substances 0.000 claims abstract description 21
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 16
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 20
- 239000000178 monomer Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 238000002156 mixing Methods 0.000 claims description 10
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 8
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical group O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 claims description 7
- 239000002202 Polyethylene glycol Substances 0.000 claims description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000012615 aggregate Substances 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- ANJPRQPHZGHVQB-UHFFFAOYSA-N hexyl isocyanate Chemical compound CCCCCCN=C=O ANJPRQPHZGHVQB-UHFFFAOYSA-N 0.000 claims 1
- 125000003700 epoxy group Chemical group 0.000 abstract 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000004568 cement Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 10
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 9
- 125000005442 diisocyanate group Chemical group 0.000 description 9
- 238000007792 addition Methods 0.000 description 8
- 238000004364 calculation method Methods 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 230000002209 hydrophobic effect Effects 0.000 description 6
- 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 6
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 5
- -1 glycol monomethyl ether alcohols Chemical class 0.000 description 5
- 238000005829 trimerization reaction Methods 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 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 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- 239000004566 building material Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000010881 fly ash Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000004575 stone Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229920003169 water-soluble polymer Polymers 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 239000011398 Portland cement Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 125000003010 ionic group Chemical group 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000011435 rock Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 150000003673 urethanes Chemical class 0.000 description 2
- 239000007762 w/o emulsion Substances 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical class C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- NLQMSBJFLQPLIJ-UHFFFAOYSA-N (3-methyloxetan-3-yl)methanol Chemical compound OCC1(C)COC1 NLQMSBJFLQPLIJ-UHFFFAOYSA-N 0.000 description 1
- VNMOIBZLSJDQEO-UHFFFAOYSA-N 1,10-diisocyanatodecane Chemical compound O=C=NCCCCCCCCCCN=C=O VNMOIBZLSJDQEO-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- OUJCKESIGPLCRN-UHFFFAOYSA-N 1,5-diisocyanato-2,2-dimethylpentane Chemical compound O=C=NCC(C)(C)CCCN=C=O OUJCKESIGPLCRN-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-Methylcyclohexanone Natural products CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 1
- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical group N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 description 1
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 239000011401 Portland-fly ash cement Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 1
- 239000011400 blast furnace cement Substances 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- 235000012255 calcium oxide Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
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- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical compound OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
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- 230000002708 enhancing effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000010438 granite Substances 0.000 description 1
- MHIBEGOZTWERHF-UHFFFAOYSA-N heptane-1,1-diol Chemical compound CCCCCCC(O)O MHIBEGOZTWERHF-UHFFFAOYSA-N 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 229920013746 hydrophilic polyethylene oxide Polymers 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- COPLXRFZXQINJM-UHFFFAOYSA-N isocyanic acid;hydrate Chemical compound O.N=C=O COPLXRFZXQINJM-UHFFFAOYSA-N 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SQFPIYFVBDSJCK-UHFFFAOYSA-N n-methylmethanamine;phenol Chemical compound C[NH2+]C.[O-]C1=CC=CC=C1 SQFPIYFVBDSJCK-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- HXSACZWWBYWLIS-UHFFFAOYSA-N oxadiazine-4,5,6-trione Chemical group O=C1ON=NC(=O)C1=O HXSACZWWBYWLIS-UHFFFAOYSA-N 0.000 description 1
- URLKBWYHVLBVBO-UHFFFAOYSA-N p-dimethylbenzene Natural products CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000011495 polyisocyanurate Substances 0.000 description 1
- 229920000582 polyisocyanurate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011513 prestressed concrete Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 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
- C08G18/28—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
- C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B26/00—Compositions of mortars, concrete or artificial stone, containing only organic binders, e.g. polymer or resin concrete
- C04B26/02—Macromolecular compounds
- C04B26/10—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C04B26/16—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
- C04B24/24—Macromolecular compounds
- C04B24/28—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C04B24/282—Polyurethanes; Polyisocyanates
-
- 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
- C08G18/70—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
- 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
- C08G2115/00—Oligomerisation
- C08G2115/02—Oligomerisation to isocyanurate groups
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Ceramic Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Dispersion Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Curing Cements, Concrete, And Artificial Stone (AREA)
- Aftertreatments Of Artificial And Natural Stones (AREA)
- Glass Compositions (AREA)
- On-Site Construction Work That Accompanies The Preparation And Application Of Concrete (AREA)
- Paints Or Removers (AREA)
- Silicon Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19654429A DE19654429A1 (de) | 1996-12-24 | 1996-12-24 | Wasserdispergierbare Polyisocyanatgemische als Additive für Beton |
| DE19654429.7 | 1996-12-24 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH10203855A JPH10203855A (ja) | 1998-08-04 |
| JPH10203855A5 JPH10203855A5 (enExample) | 2005-07-28 |
| JP3946332B2 true JP3946332B2 (ja) | 2007-07-18 |
Family
ID=7816261
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP36481697A Expired - Fee Related JP3946332B2 (ja) | 1996-12-24 | 1997-12-22 | コンクリート添加剤としての非イオン型の水分散性ポリイソシアネートの使用 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6007619A (enExample) |
| EP (1) | EP0850896B9 (enExample) |
| JP (1) | JP3946332B2 (enExample) |
| KR (1) | KR100531705B1 (enExample) |
| CN (1) | CN1088047C (enExample) |
| AT (1) | ATE236104T1 (enExample) |
| CA (1) | CA2224956C (enExample) |
| DE (2) | DE19654429A1 (enExample) |
| DK (1) | DK0850896T3 (enExample) |
| ES (1) | ES2195074T3 (enExample) |
| MX (1) | MX201523B (enExample) |
| TW (1) | TW422867B (enExample) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19740454A1 (de) * | 1997-09-15 | 1999-03-18 | Bayer Ag | Wasserdispergierbare bzw. wasserlösliche Polyurethane als Additive für Beton |
| DE19805022A1 (de) * | 1998-02-09 | 1999-08-12 | Koester Bauchemie Gmbh | Abdichtungssystem |
| DE19822890A1 (de) * | 1998-05-22 | 1999-11-25 | Bayer Ag | Neue wäßrige 2 K-PUR-Beschichtungssysteme |
| ES2209274T3 (es) * | 1998-05-22 | 2004-06-16 | Bayer Aktiengesellschaft | Mezclas de poliisocianatos modificadas mediante polieteres dispersables. |
| FR2780396B1 (fr) * | 1998-06-30 | 2000-08-04 | Coatex Sa | Nouveaux agents de type polycondensat pour ameliorer la maniabilite des liants hydrauliques, leur procede de preparation, les liants les contenant et leurs applications |
| DE19958170A1 (de) * | 1999-12-02 | 2001-06-07 | Bayer Ag | Hochfunktionelle wasserdispergierbare Polyisocyanatgemische |
| MXPA02008041A (es) * | 2000-02-18 | 2004-09-06 | Stroup Willie W | Mezcla de cemento de escoria de cubilote y metodos para elaborar y usar la misma. |
| KR20010007776A (ko) * | 2000-09-06 | 2001-02-05 | 김형봉 | 시멘트 도로 및 구체의 균열 파손을 빠르게 성형 복구하는초속 성형 복구재의 제조방법과 이를 이용한 시공공법 |
| US6709758B2 (en) * | 2001-11-09 | 2004-03-23 | Lord Corporation | Room temperature curable X-HNBR coating |
| KR20030052218A (ko) * | 2001-12-20 | 2003-06-26 | 한일종합실란트 주식회사 | 콘크리트 도로 및 공항 상부 단면 파손 복구재 콘크리트급조 성형재 제조기술 |
| US6777026B2 (en) * | 2002-10-07 | 2004-08-17 | Lord Corporation | Flexible emissive coatings for elastomer substrates |
| US6838516B2 (en) | 2002-07-26 | 2005-01-04 | Great Eastern Resins Industrial Co., Ltd. | Water dispersible polyisocyanate composition and its uses |
| CA2627509C (en) | 2005-11-15 | 2013-10-22 | Valspar Sourcing, Inc. | Crush resistant latex topcoat composition for fiber cement substrates |
| US9783622B2 (en) | 2006-01-31 | 2017-10-10 | Axalta Coating Systems Ip Co., Llc | Coating system for cement composite articles |
| US8293361B2 (en) | 2006-01-31 | 2012-10-23 | Valspar Sourcing, Inc. | Coating system for cement composite articles |
| DE102006011153A1 (de) * | 2006-03-10 | 2007-09-13 | Construction Research & Technology Gmbh | Fluormodifiziertes Zusatzmittel für zementäre Produkte, Verfahren zu seiner Herstellung und dessen Verwendung |
| MX2008014749A (es) | 2006-05-19 | 2009-02-04 | Valspar Sourcing Inc | Sistema de recubrimiento para articulos compuestos de cemento. |
| EP2035516B2 (en) * | 2006-06-02 | 2017-01-04 | Valspar Sourcing, Inc. | High performance aqueous coating compositions |
| EP2043967B1 (en) | 2006-07-07 | 2018-07-04 | Valspar Sourcing, Inc. | Coating systems for cement composite articles |
| US8415009B2 (en) * | 2006-12-13 | 2013-04-09 | James Hardie Technology Limited | Engineered composite building materials and methods of making same |
| JP5130723B2 (ja) * | 2007-01-22 | 2013-01-30 | Ｄｉｃ株式会社 | ウレタンセメント系組成物、床材及びその施工方法 |
| US8202581B2 (en) | 2007-02-16 | 2012-06-19 | Valspar Sourcing, Inc. | Treatment for cement composite articles |
| US8490916B2 (en) | 2007-10-19 | 2013-07-23 | Lord Corporation | Suspension system for aircraft auxiliary power unit with elastomeric member |
| BRPI0917455B1 (pt) | 2008-08-15 | 2018-11-21 | Valspar Sourcing Inc | composição de revestimento, método para preparar um artigo revestido, e, artigo revestido |
| AU2009316285A1 (en) | 2008-11-24 | 2010-05-27 | Valspar Sourcing, Inc. | Coating system for cement composite articles |
| CN101787771B (zh) * | 2010-02-26 | 2012-01-11 | 哈尔滨工业大学深圳研究生院 | 用外加剂产生二氧化碳制备的再生混凝土构件及制备方法 |
| CN101793076B (zh) * | 2010-02-26 | 2011-09-14 | 哈尔滨工业大学深圳研究生院 | 用外加剂产生二氧化碳制备的混凝土构件及制备方法 |
| EP2365013A1 (de) * | 2010-03-12 | 2011-09-14 | Rhein Chemie Rheinau GmbH | Neue witterungsbeständige Polyurethangiessmassen, ein Verfahren zu deren Herstellung und deren Verwendung |
| JP2014520919A (ja) | 2011-07-08 | 2014-08-25 | 江蘇博特新材料有限公司 | 水分散両性ポリウレタン、調製方法及びそのコンクリート靱性増強への応用 |
| CN102786272B (zh) * | 2012-05-04 | 2014-10-01 | 武汉理工大学 | 一种高延展性致密匀质c60海洋混凝土及其制备方法 |
| EP2849941A1 (en) | 2012-05-14 | 2015-03-25 | Basf Se | Moisture-resistant gypsum boards and slurries for making same |
| PL2990398T3 (pl) | 2014-08-29 | 2019-06-28 | Covestro Deutschland Ag | Hydrofilne estry kwasu poliasparginowego |
| CN104529219B (zh) * | 2014-12-04 | 2017-01-11 | 江苏科技大学 | 一种水泥稳泡剂及其水泥组合物及应用方法 |
| CN104945634A (zh) * | 2015-06-02 | 2015-09-30 | 江苏奥莱特新材料有限公司 | 一种氨酯型缓凝聚羧酸系减水剂的制备方法 |
| JP6995475B2 (ja) * | 2016-12-27 | 2022-02-04 | コベストロ、ドイチュラント、アクチエンゲゼルシャフト | 無黄変セメント系ポリウレタン発泡複合体及びその製造方法 |
| EP4015546A1 (de) | 2020-12-15 | 2022-06-22 | Covestro Deutschland AG | Nichtionisch hydrophilierte polyisocyanate mit sehr niedrigem monomergehalt |
| CN120693357A (zh) | 2023-06-01 | 2025-09-23 | 洛德公司 | 储存稳定的导热反应性复合物和方法 |
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| GB1192864A (en) * | 1968-05-13 | 1970-05-20 | Ici Ltd | New Cement Compositions |
| US4211680A (en) * | 1968-05-13 | 1980-07-08 | Imperial Chemical Industries Limited | Quick-set compositions of hydraulic cement, silica, water, polyisocyanate and polyol |
| BE793375A (fr) * | 1972-01-03 | 1973-06-27 | Ici Ltd | Nouvelles compositions cimentaires |
| JPS506213A (enExample) * | 1973-05-17 | 1975-01-22 | ||
| DE2325090C3 (de) * | 1973-05-17 | 1980-11-06 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von als kolloides Xerosol vorliegendem anorganischorganischem Polymer-Polykieselsäure-Verbundmaterial |
| DE2359611C3 (de) * | 1973-11-30 | 1981-09-17 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von durch Harze auf Isocyanatbasis gebundenen Füllstoffen |
| JPS50139121A (enExample) * | 1974-04-24 | 1975-11-06 | ||
| GB1491216A (en) * | 1974-04-30 | 1977-11-09 | Ici Ltd | Cement compositions |
| US4153470A (en) * | 1975-10-15 | 1979-05-08 | Hoechst Aktiengesellschaft | Process for preparing foamed gypsum and constructional elements composed thereof |
| SU618358A1 (ru) * | 1977-02-17 | 1978-08-05 | Всесоюзный Ордена Трудового Красного Знамени Научно-Исследовательский Институт Железнодорожного Транспорта | Полимербетонна смесь |
| US4143014A (en) * | 1977-11-09 | 1979-03-06 | The Upjohn Company | Novel compositions |
| US4228053A (en) * | 1979-01-29 | 1980-10-14 | The Upjohn Company | Concrete preparation with aqueous solution of product from polyether with polymethylene polyphenyl polyisocyanate |
| DE2927578C2 (de) * | 1979-07-07 | 1982-07-01 | Holzwerk Osterwald GmbH, 3216 Salzhemmendorf | Verfahren zur Herstellung nichtbrennbarer flächiger Körper für Bau-, Dämm-, Möbelbau- und Innenausbeiteile |
| SU1143723A1 (ru) * | 1982-05-03 | 1985-03-07 | Московский научно-исследовательский и проектный институт жилищного хозяйства | Полимерцементбетонна смесь |
| SU1147703A1 (ru) * | 1983-06-30 | 1985-03-30 | Московский Научно-Исследовательский И Проектный Институт Жилищного Хозяйства "Мосжилниипроект" | Полимерраствор дл покрыти и приклеивани |
| SU1208059A1 (ru) * | 1984-03-05 | 1986-01-30 | Московский Инженерно-Строительный Институт Им.В.В.Куйбышева | Герметизирующий компаунд |
| US4630963A (en) * | 1984-09-05 | 1986-12-23 | Wyman Ransome J | Polymer concrete by percolation |
| FR2572722B1 (fr) * | 1984-11-06 | 1991-11-29 | Cerib | Procede de carbonatation du beton |
| DE3521618A1 (de) * | 1985-06-15 | 1986-12-18 | Bayer Ag, 5090 Leverkusen | In wasser dispergierbare polyisocyanat-zubereitung und ihre verwendung als zusatzmittel fuer waessrige klebstoffe |
| JPH0755851B2 (ja) * | 1987-02-20 | 1995-06-14 | 宇部興産株式会社 | 高強度セメント硬化体及びその製造方法 |
| US5086175A (en) * | 1988-12-28 | 1992-02-04 | Takeda Chemical Industries, Ltd. | Polyisocyanates, their production and uses |
| CA2072167C (en) * | 1991-07-22 | 2001-12-18 | Terry A. Potter | Polyisocyanates containing allophanate and isocyanurate groups, a process for their production and their use in two-component coating compositions |
| US5235018A (en) * | 1991-07-22 | 1993-08-10 | Miles Inc. | Polyisocyanates containing allophanate and isocyanurate groups, a process for their production and their use in two-component coating compositions |
| US5200489A (en) * | 1992-02-27 | 1993-04-06 | Miles Inc. | Water dispersible polyisocyanates |
| DE4136618A1 (de) * | 1991-11-07 | 1993-05-13 | Bayer Ag | Wasserdispergierbare polyisocyanatgemische |
| EP0566037A2 (en) * | 1992-04-14 | 1993-10-20 | Takeda Chemical Industries, Ltd. | Polyisocyanates, their production and use |
| DE4416113A1 (de) * | 1994-05-06 | 1995-11-09 | Bayer Ag | Wasserdispergierbare Polyisocyanat-Zubereitungen |
| DE4416321A1 (de) * | 1994-05-09 | 1995-11-16 | Bayer Ag | Verfahren zur Herstellung von Allophanatgruppen aufweisenden lichtechten Polyisocyanaten |
| JPH08183646A (ja) * | 1994-12-28 | 1996-07-16 | Aron Kasei Co Ltd | 改良された熱可塑性セメント組成物及びその製造方法 |
| JPH08217516A (ja) * | 1995-02-10 | 1996-08-27 | Toubu Kagaku Kk | 改良された熱可塑性セメントの製造方法 |
| DE19506534A1 (de) * | 1995-02-24 | 1996-08-29 | Bayer Ag | Wasserdispergierbare Polyisocyanatgemische |
| JP3088632B2 (ja) * | 1995-03-06 | 2000-09-18 | 三洋化成工業株式会社 | 左官モルタル用混和剤 |
| US5725654A (en) * | 1997-06-06 | 1998-03-10 | Arco Chemical Technology, L.P. | Cement composition |
-
1996
- 1996-12-24 DE DE19654429A patent/DE19654429A1/de not_active Withdrawn
-
1997
- 1997-12-11 US US08/988,575 patent/US6007619A/en not_active Expired - Fee Related
- 1997-12-12 AT AT97121921T patent/ATE236104T1/de active
- 1997-12-12 DE DE59709688T patent/DE59709688D1/de not_active Expired - Lifetime
- 1997-12-12 ES ES97121921T patent/ES2195074T3/es not_active Expired - Lifetime
- 1997-12-12 DK DK97121921T patent/DK0850896T3/da active
- 1997-12-12 EP EP97121921A patent/EP0850896B9/de not_active Expired - Lifetime
- 1997-12-16 CA CA002224956A patent/CA2224956C/en not_active Expired - Fee Related
- 1997-12-17 TW TW086119024A patent/TW422867B/zh not_active IP Right Cessation
- 1997-12-18 MX MX9710337A patent/MX201523B/es not_active IP Right Cessation
- 1997-12-22 JP JP36481697A patent/JP3946332B2/ja not_active Expired - Fee Related
- 1997-12-23 KR KR1019970072503A patent/KR100531705B1/ko not_active Expired - Fee Related
- 1997-12-24 CN CN97126255A patent/CN1088047C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1189471A (zh) | 1998-08-05 |
| ES2195074T3 (es) | 2003-12-01 |
| DE59709688D1 (de) | 2003-05-08 |
| ATE236104T1 (de) | 2003-04-15 |
| JPH10203855A (ja) | 1998-08-04 |
| KR100531705B1 (ko) | 2006-01-27 |
| EP0850896A1 (de) | 1998-07-01 |
| CA2224956A1 (en) | 1998-06-24 |
| TW422867B (en) | 2001-02-21 |
| CA2224956C (en) | 2007-07-31 |
| DK0850896T3 (da) | 2003-07-07 |
| CN1088047C (zh) | 2002-07-24 |
| EP0850896B1 (en) | 2003-04-02 |
| US6007619A (en) | 1999-12-28 |
| EP0850896B9 (de) | 2003-10-22 |
| MX9710337A (es) | 1998-08-30 |
| KR19980064514A (ko) | 1998-10-07 |
| DE19654429A1 (de) | 1998-06-25 |
| MX201523B (es) | 2001-04-24 |
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