CA2292510C - Method for producing closed-cell rigid polyurethane foams having low thermal conductivity - Google Patents
Method for producing closed-cell rigid polyurethane foams having low thermal conductivity Download PDFInfo
- Publication number
- CA2292510C CA2292510C CA002292510A CA2292510A CA2292510C CA 2292510 C CA2292510 C CA 2292510C CA 002292510 A CA002292510 A CA 002292510A CA 2292510 A CA2292510 A CA 2292510A CA 2292510 C CA2292510 C CA 2292510C
- Authority
- CA
- Canada
- Prior art keywords
- weight
- polyether
- polyol component
- molecular weight
- oxide content
- 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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- 229920005830 Polyurethane Foam Polymers 0.000 title claims abstract description 4
- 239000011496 polyurethane foam Substances 0.000 title claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 229920005862 polyol Polymers 0.000 claims abstract description 34
- 150000003077 polyols Chemical class 0.000 claims abstract description 31
- 229920000570 polyether Polymers 0.000 claims abstract description 28
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 27
- 239000004088 foaming agent Substances 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 11
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims abstract description 6
- 229930006000 Sucrose Natural products 0.000 claims abstract description 6
- 239000005720 sucrose Substances 0.000 claims abstract description 6
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims abstract description 5
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims abstract description 5
- 239000000654 additive Substances 0.000 claims abstract description 5
- 239000000600 sorbitol Substances 0.000 claims abstract description 5
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000006057 Non-nutritive feed additive Substances 0.000 claims abstract 2
- 230000000996 additive effect Effects 0.000 claims abstract 2
- 150000004982 aromatic amines Chemical class 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 23
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 20
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 20
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 12
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 11
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 8
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 8
- 229920001451 polypropylene glycol Polymers 0.000 claims description 5
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 4
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- 150000001924 cycloalkanes Chemical class 0.000 claims description 3
- 239000001282 iso-butane Substances 0.000 claims description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 3
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 claims description 2
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 description 18
- 239000004814 polyurethane Substances 0.000 description 13
- 229920002635 polyurethane Polymers 0.000 description 13
- 238000009472 formulation Methods 0.000 description 12
- 239000012948 isocyanate Substances 0.000 description 9
- 150000002513 isocyanates Chemical class 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- -1 aliphatic hydrocarbon radical Chemical class 0.000 description 7
- 238000005187 foaming Methods 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- FRCHKSNAZZFGCA-UHFFFAOYSA-N 1,1-dichloro-1-fluoroethane Chemical compound CC(F)(Cl)Cl FRCHKSNAZZFGCA-UHFFFAOYSA-N 0.000 description 4
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 4
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 230000008014 freezing Effects 0.000 description 3
- 238000007710 freezing Methods 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 3
- 238000005057 refrigeration Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 2
- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 230000001408 fungistatic effect Effects 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000005828 hydrofluoroalkanes Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical group OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 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
- CXIGIYYQHHRBJC-UHFFFAOYSA-N 1,1,1,4,4,4-hexafluorobutane Chemical compound FC(F)(F)CCC(F)(F)F CXIGIYYQHHRBJC-UHFFFAOYSA-N 0.000 description 1
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- FCQPNTOQFPJCMF-UHFFFAOYSA-N 1,3-bis[3-(dimethylamino)propyl]urea Chemical compound CN(C)CCCNC(=O)NCCCN(C)C FCQPNTOQFPJCMF-UHFFFAOYSA-N 0.000 description 1
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
- GEEGPFGTMRWCID-UHFFFAOYSA-N 1-n,1-n,1-n',1-n'-tetramethylbutane-1,1-diamine Chemical compound CCCC(N(C)C)N(C)C GEEGPFGTMRWCID-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-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
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- 229940075142 2,5-diaminotoluene Drugs 0.000 description 1
- OHKOAJUTRVTYSW-UHFFFAOYSA-N 2-[(2-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1N OHKOAJUTRVTYSW-UHFFFAOYSA-N 0.000 description 1
- UTNMPUFESIRPQP-UHFFFAOYSA-N 2-[(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC=C1N UTNMPUFESIRPQP-UHFFFAOYSA-N 0.000 description 1
- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 description 1
- WMNWJTDAUWBXFJ-UHFFFAOYSA-N 3,3,4-trimethylheptane-2,2-diamine Chemical compound CCCC(C)C(C)(C)C(C)(N)N WMNWJTDAUWBXFJ-UHFFFAOYSA-N 0.000 description 1
- WAPWXMDDHHWKNM-UHFFFAOYSA-N 3-[2,3-bis[3-(dimethylamino)propyl]triazinan-1-yl]-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCN1CCCN(CCCN(C)C)N1CCCN(C)C WAPWXMDDHHWKNM-UHFFFAOYSA-N 0.000 description 1
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
- AXNUJYHFQHQZBE-UHFFFAOYSA-N 3-methylbenzene-1,2-diamine Chemical compound CC1=CC=CC(N)=C1N AXNUJYHFQHQZBE-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- CQQXCSFSYHAZOO-UHFFFAOYSA-L [acetyloxy(dioctyl)stannyl] acetate Chemical compound CCCCCCCC[Sn](OC(C)=O)(OC(C)=O)CCCCCCCC CQQXCSFSYHAZOO-UHFFFAOYSA-L 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 210000003850 cellular structure Anatomy 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 229960002887 deanol Drugs 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
- PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 239000012971 dimethylpiperazine Substances 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000004872 foam stabilizing agent Substances 0.000 description 1
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- FJIKWRGCXUCUIG-UHFFFAOYSA-N lormetazepam Chemical compound N=1C(O)C(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1Cl FJIKWRGCXUCUIG-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- XFLSMWXCZBIXLV-UHFFFAOYSA-N n,n-dimethyl-2-(4-methylpiperazin-1-yl)ethanamine Chemical compound CN(C)CCN1CCN(C)CC1 XFLSMWXCZBIXLV-UHFFFAOYSA-N 0.000 description 1
- WFBDWTZOYPUBQZ-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]formamide Chemical compound CN(C)CCCNC=O WFBDWTZOYPUBQZ-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- DYFXGORUJGZJCA-UHFFFAOYSA-N phenylmethanediamine Chemical class NC(N)C1=CC=CC=C1 DYFXGORUJGZJCA-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005903 polyol mixture Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- ADRDEXBBJTUCND-UHFFFAOYSA-N pyrrolizidine Chemical compound C1CCN2CCCC21 ADRDEXBBJTUCND-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000005437 stratosphere Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
- C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
- C08J9/141—Hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4804—Two or more polyethers of different physical or chemical nature
- C08G18/482—Mixtures of polyethers containing at least one polyether containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
- C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
- C08J9/143—Halogen containing compounds
- C08J9/144—Halogen containing compounds containing carbon, halogen and hydrogen 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
- C08G2110/00—Foam properties
- C08G2110/0025—Foam properties rigid
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0041—Foam properties having specified density
- C08G2110/005—< 50kg/m3
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2205/00—Foams characterised by their properties
- C08J2205/10—Rigid foams
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19723193.4 | 1997-06-03 | ||
| DE19723193A DE19723193A1 (de) | 1997-06-03 | 1997-06-03 | Verfahren zur Herstellung von geschlossenzelligen Polyurethan-Hartschaumstoffen mit geringer Wärmeleitfähigkeit |
| PCT/EP1998/003039 WO1998055528A1 (de) | 1997-06-03 | 1998-05-22 | Verfahren zur herstellung von geschlossenzelligen polyurethan-hartschaumstoffen mit geringer wärmeleitfähigkeit |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2292510A1 CA2292510A1 (en) | 1998-12-10 |
| CA2292510C true CA2292510C (en) | 2007-09-18 |
Family
ID=7831244
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002292510A Expired - Fee Related CA2292510C (en) | 1997-06-03 | 1998-05-22 | Method for producing closed-cell rigid polyurethane foams having low thermal conductivity |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6306920B1 (enExample) |
| EP (1) | EP0991686B1 (enExample) |
| JP (1) | JP4761591B2 (enExample) |
| CN (1) | CN1138804C (enExample) |
| AT (1) | ATE211749T1 (enExample) |
| AU (1) | AU7915098A (enExample) |
| BR (1) | BR9809930B1 (enExample) |
| CA (1) | CA2292510C (enExample) |
| DE (2) | DE19723193A1 (enExample) |
| DK (1) | DK0991686T3 (enExample) |
| ES (1) | ES2171029T3 (enExample) |
| PT (1) | PT991686E (enExample) |
| RU (1) | RU2222549C2 (enExample) |
| SI (1) | SI0991686T1 (enExample) |
| TR (1) | TR199903017T2 (enExample) |
| WO (1) | WO1998055528A1 (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60220591T2 (de) * | 2001-07-02 | 2008-02-14 | Tosoh Corp., Shinnanyo | Verfahren zur Herstellung eines Polyurethanhartschaumstoffes |
| EP2500368A3 (en) * | 2002-07-15 | 2012-11-28 | Tosoh Corporation | Catalyst and process for producing a rigid polyurethane foam |
| US6846850B2 (en) * | 2003-01-22 | 2005-01-25 | Bayer Materialscience Llc | Rigid polyurethane foams with improved properties |
| KR100935517B1 (ko) * | 2003-03-07 | 2010-01-06 | 엘지전자 주식회사 | 접착력과 탈형성이 개선된 폴리우레탄 발포체 제조를 위한원액 조성물, 이로부터 제조된 폴리우레탄 발포체 및 그제조방법 |
| US20050137315A1 (en) * | 2003-08-08 | 2005-06-23 | Aksay Ilhan A. | L3-silica/polyurethane thermally insulating nanocomposite |
| JP4927552B2 (ja) * | 2003-11-03 | 2012-05-09 | ダウ グローバル テクノロジーズ エルエルシー | トルエンジアミン開始ポリオールをベースにする硬質ポリウレタンフォーム |
| US20050148677A1 (en) * | 2003-12-30 | 2005-07-07 | Elsken Kevin J. | Low K-factor rigid foam systems |
| JP4736503B2 (ja) * | 2004-03-31 | 2011-07-27 | 旭硝子株式会社 | 硬質発泡合成樹脂の製造方法 |
| DE102004048728A1 (de) * | 2004-10-05 | 2006-04-06 | Basf Ag | Verfahren zur Herstellung von Polyurethan-Hartschaumstoffen |
| KR101398244B1 (ko) | 2005-11-14 | 2014-05-22 | 다우 글로벌 테크놀로지스 엘엘씨 | 향상된 열 전도성을 갖는 강성 폴리우레탄 발포체의 성형방법 |
| JP5189254B2 (ja) * | 2006-06-13 | 2013-04-24 | アキレス株式会社 | 発泡樹脂断熱材 |
| CN101578314B (zh) * | 2007-01-12 | 2012-01-18 | 巴斯夫欧洲公司 | 硬质聚氨酯泡沫 |
| WO2008094238A1 (en) * | 2007-01-30 | 2008-08-07 | Dow Global Technologies, Inc. | Ortho-cyclohexanediamine-initiated polyols and rigid polyurethane foam made therefrom |
| RU2452742C2 (ru) * | 2007-01-30 | 2012-06-10 | ДАУ ГЛОБАЛ ТЕКНОЛОДЖИЗ ЭлЭлСи | Инициированные аминами полиолы и жесткие полиуретановые пенопласты, изготовленные из них |
| ES2375337T3 (es) * | 2008-01-17 | 2012-02-29 | Dow Global Technologies Llc | Espumas basadas en isocianato aislantes térmicamente. |
| CN101357979B (zh) * | 2008-08-20 | 2011-06-29 | 江苏科技大学 | 一种耐低温lng保温材料及其制备方法 |
| ES2405684T3 (es) * | 2009-03-24 | 2013-06-03 | Dow Global Technologies Llc | Producción de espumas rígidas de poliuretano y el uso de las mismas |
| AT508870B1 (de) * | 2009-09-16 | 2015-11-15 | Alutechnik Matauschek Gmbh | Isolierteil |
| RU2597931C2 (ru) * | 2011-04-07 | 2016-09-20 | Басф Се | Способ получения жестких полиуретановых пенопластов |
| WO2013017554A1 (de) * | 2011-08-01 | 2013-02-07 | Basf Se | Hfo/wassergetriebene hartschaum-systeme |
| EP3458492A4 (en) * | 2016-05-20 | 2020-02-19 | Covestro Deutschland AG | POLYURETHANE FOAM AND POLYURETHANE COMPOSITE CONTAINING THE SAME |
| CN107163219A (zh) * | 2017-05-19 | 2017-09-15 | 美的集团股份有限公司 | 聚氨酯泡沫的发泡配方、制备方法和聚氨酯泡沫保温材料 |
| CN107903366B (zh) * | 2017-11-14 | 2019-08-30 | 美的集团股份有限公司 | 用于聚氨酯发泡的催化剂、聚氨酯发泡组合物及其发泡方法与应用 |
| WO2019194966A1 (en) * | 2018-04-03 | 2019-10-10 | Dow Global Technologies Llc | Foam formulations |
| US10640600B2 (en) * | 2018-04-24 | 2020-05-05 | Covestro Llc | Rigid polyurethane foams suitable for use as panel insulation |
| WO2020223059A1 (en) * | 2019-04-29 | 2020-11-05 | Covestro Llc | Rigid polyurethane foams suitable for use as panel insulation |
| CN110305282A (zh) * | 2019-07-04 | 2019-10-08 | 长虹美菱股份有限公司 | 一种负压发泡冰箱的隔热层配方及发泡工艺 |
| US11773586B2 (en) * | 2020-06-05 | 2023-10-03 | Johns Manville | Non-wicking underlayment board |
| US11685140B2 (en) * | 2020-06-05 | 2023-06-27 | Johns Manville | Non-wicking underlayment board |
| CN116731381B (zh) * | 2023-05-16 | 2025-01-28 | 四川大学 | 一种含二氧化碳加合物的液态发泡剂 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59100124A (ja) * | 1982-11-30 | 1984-06-09 | Asahi Oorin Kk | 硬質フオ−ムの成形方法 |
| SU1497188A1 (ru) * | 1985-12-25 | 1989-07-30 | Белорусский технологический институт им.С.М.Кирова | Композици дл получени жесткого пенополиуретана |
| JPH0196209A (ja) * | 1987-10-09 | 1989-04-14 | Hitachi Ltd | 硬質ポリウレタンフォームの製造方法 |
| DE3818692A1 (de) | 1988-06-01 | 1989-12-07 | Bayer Ag | Verwendung von 1,1,1,4,4,4-hexafluorbutan als treib- und daemmgas fuer die herstellung von kunststoff-schaumstoffen |
| JPH02284912A (ja) * | 1989-04-27 | 1990-11-22 | Hitachi Ltd | 硬質ポリウレタンフォーム及びその製造方法と断熱材並びにそれを用いた冷蔵庫 |
| JP2653884B2 (ja) * | 1989-09-04 | 1997-09-17 | 株式会社日立製作所 | 硬質ポリウレタンフォーム及びその製造方法と断熱材並びにそれを用いた冷蔵庫 |
| DE3933335C2 (de) | 1989-10-06 | 1998-08-06 | Basf Ag | Verfahren zur Herstellung von Polyurethan-Hartschaumstoffen mit geringer Wärmeleitfähigkeit und ihre Verwendung |
| JP2897888B2 (ja) * | 1990-02-20 | 1999-05-31 | 株式会社日立製作所 | 硬質ポリウレタンフォームとその製造方法およびそれを用いた製品 |
| JP3149132B2 (ja) * | 1990-08-24 | 2001-03-26 | 株式会社日立製作所 | 硬質ポリウレタンフォームを用いた冷蔵庫 |
| US5272183A (en) | 1991-09-20 | 1993-12-21 | Miles Inc. | HCFC blown rigid foams with low thermal conductivity |
| DE4321204C2 (de) * | 1993-06-25 | 1997-09-18 | Basf Ag | Verfahren zur Herstellung von Polyurethan-Hartschaumstoffen |
| JPH07206966A (ja) * | 1994-01-20 | 1995-08-08 | Sanyo Chem Ind Ltd | 硬質ポリウレタンフォームの製造法 |
| DE4437859A1 (de) * | 1994-10-22 | 1996-04-25 | Elastogran Gmbh | Verfahren zur Herstellung von Polyurethan-Hartschaumstoffen mit einer verminderten Wärmeleitfähigkeit und ihre Verwendung |
| JP3419584B2 (ja) * | 1995-04-03 | 2003-06-23 | 花王株式会社 | ポリウレタンフォームの製造方法 |
| DE19512470A1 (de) * | 1995-04-04 | 1996-10-10 | Bayer Ag | Verfahren zur Herstellung von besonders vorteilhaften flammwidrigen, halogenfreien Polyurethan-Polyharnstoffen |
| BR9611205A (pt) * | 1995-11-01 | 1999-03-30 | Basf Corp | Processo de produção de uma espuma de célula fechada rígida à base de poliisocianato e composição de poliol estável em armazenamento |
| US5648019A (en) * | 1995-11-01 | 1997-07-15 | Basf Corporation | Three component polyol blend for use in insulating rigid polyurethane foams |
| US5523334A (en) * | 1995-11-01 | 1996-06-04 | Basf Corporation | Insulating rigid polyurethane foams |
-
1997
- 1997-06-03 DE DE19723193A patent/DE19723193A1/de not_active Withdrawn
-
1998
- 1998-05-22 JP JP50141099A patent/JP4761591B2/ja not_active Expired - Lifetime
- 1998-05-22 RU RU2000100993/04A patent/RU2222549C2/ru active
- 1998-05-22 US US09/424,093 patent/US6306920B1/en not_active Expired - Lifetime
- 1998-05-22 DE DE59802846T patent/DE59802846D1/de not_active Expired - Lifetime
- 1998-05-22 DK DK98929365T patent/DK0991686T3/da active
- 1998-05-22 BR BRPI9809930-2A patent/BR9809930B1/pt not_active IP Right Cessation
- 1998-05-22 WO PCT/EP1998/003039 patent/WO1998055528A1/de not_active Ceased
- 1998-05-22 PT PT98929365T patent/PT991686E/pt unknown
- 1998-05-22 ES ES98929365T patent/ES2171029T3/es not_active Expired - Lifetime
- 1998-05-22 TR TR1999/03017T patent/TR199903017T2/xx unknown
- 1998-05-22 CA CA002292510A patent/CA2292510C/en not_active Expired - Fee Related
- 1998-05-22 SI SI9830080T patent/SI0991686T1/xx unknown
- 1998-05-22 AU AU79150/98A patent/AU7915098A/en not_active Abandoned
- 1998-05-22 CN CNB988057948A patent/CN1138804C/zh not_active Expired - Lifetime
- 1998-05-22 EP EP98929365A patent/EP0991686B1/de not_active Expired - Lifetime
- 1998-05-22 AT AT98929365T patent/ATE211749T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU7915098A (en) | 1998-12-21 |
| CN1259149A (zh) | 2000-07-05 |
| ATE211749T1 (de) | 2002-01-15 |
| BR9809930A (pt) | 2000-08-01 |
| JP4761591B2 (ja) | 2011-08-31 |
| DE19723193A1 (de) | 1998-12-10 |
| WO1998055528A1 (de) | 1998-12-10 |
| PT991686E (pt) | 2002-06-28 |
| ES2171029T3 (es) | 2002-08-16 |
| US6306920B1 (en) | 2001-10-23 |
| JP2002502455A (ja) | 2002-01-22 |
| DK0991686T3 (da) | 2002-04-22 |
| TR199903017T2 (xx) | 2000-05-22 |
| CN1138804C (zh) | 2004-02-18 |
| BR9809930B1 (pt) | 2008-11-18 |
| SI0991686T1 (en) | 2002-04-30 |
| HK1029355A1 (en) | 2001-03-30 |
| EP0991686A1 (de) | 2000-04-12 |
| CA2292510A1 (en) | 1998-12-10 |
| EP0991686B1 (de) | 2002-01-09 |
| DE59802846D1 (de) | 2002-02-28 |
| RU2222549C2 (ru) | 2004-01-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20140522 |