DE102005025970A1 - Poröse Polyisocyanat-Polyadditionsprodukte - Google Patents
Poröse Polyisocyanat-Polyadditionsprodukte Download PDFInfo
- Publication number
- DE102005025970A1 DE102005025970A1 DE102005025970A DE102005025970A DE102005025970A1 DE 102005025970 A1 DE102005025970 A1 DE 102005025970A1 DE 102005025970 A DE102005025970 A DE 102005025970A DE 102005025970 A DE102005025970 A DE 102005025970A DE 102005025970 A1 DE102005025970 A1 DE 102005025970A1
- Authority
- DE
- Germany
- Prior art keywords
- isocyanates
- solvent
- isocyanate
- reactive compounds
- reaction
- 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.)
- Withdrawn
Links
- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 10
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 10
- 239000012948 isocyanate Substances 0.000 claims abstract description 53
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 51
- 239000002904 solvent Substances 0.000 claims abstract description 50
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 239000000047 product Substances 0.000 claims description 17
- 238000001035 drying Methods 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 11
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- -1 compounds Ester Chemical class 0.000 claims description 7
- 229920005862 polyol Polymers 0.000 claims description 7
- 150000003077 polyols Chemical class 0.000 claims description 7
- 239000004970 Chain extender Substances 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 238000002429 nitrogen sorption measurement Methods 0.000 claims description 4
- 239000003431 cross linking reagent Substances 0.000 claims description 3
- 229920005830 Polyurethane Foam Polymers 0.000 claims description 2
- 239000011496 polyurethane foam Substances 0.000 claims description 2
- 239000011877 solvent mixture Substances 0.000 claims description 2
- 230000003213 activating effect Effects 0.000 claims 1
- 230000036629 mind Effects 0.000 claims 1
- 239000004814 polyurethane Substances 0.000 description 31
- 229920002635 polyurethane Polymers 0.000 description 31
- 239000000499 gel Substances 0.000 description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 239000012530 fluid Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 239000011148 porous material Substances 0.000 description 5
- 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 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001879 gelation Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000005829 trimerization reaction Methods 0.000 description 3
- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 description 2
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 2
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 2
- SMNOVRZDAZZQTI-UHFFFAOYSA-N 1-[dibutyl(dodecanoyl)stannyl]dodecan-1-one Chemical compound CCCCCCCCCCCC(=O)[Sn](CCCC)(CCCC)C(=O)CCCCCCCCCCC SMNOVRZDAZZQTI-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- YSAANLSYLSUVHB-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]ethanol Chemical compound CN(C)CCOCCO YSAANLSYLSUVHB-UHFFFAOYSA-N 0.000 description 2
- AOFIWCXMXPVSAZ-UHFFFAOYSA-N 4-methyl-2,6-bis(methylsulfanyl)benzene-1,3-diamine Chemical compound CSC1=CC(C)=C(N)C(SC)=C1N AOFIWCXMXPVSAZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241001295925 Gegenes Species 0.000 description 2
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 2
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 2
- KAEIHZNNPOMFSS-UHFFFAOYSA-N N=C=O.N=C=O.C=1C=CC=CC=1CCC1=CC=CC=C1 Chemical compound N=C=O.N=C=O.C=1C=CC=CC=1CCC1=CC=CC=C1 KAEIHZNNPOMFSS-UHFFFAOYSA-N 0.000 description 2
- 229920002396 Polyurea Polymers 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000004964 aerogel Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000010420 art technique Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- FSDSKERRNURGGO-UHFFFAOYSA-N cyclohexane-1,3,5-triol Chemical compound OC1CC(O)CC(O)C1 FSDSKERRNURGGO-UHFFFAOYSA-N 0.000 description 2
- VKONPUDBRVKQLM-UHFFFAOYSA-N cyclohexane-1,4-diol Chemical compound OC1CCC(O)CC1 VKONPUDBRVKQLM-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000011810 insulating material Substances 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 150000003606 tin compounds Chemical class 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- IKYNWXNXXHWHLL-UHFFFAOYSA-N 1,3-diisocyanatopropane Chemical compound O=C=NCCCN=C=O IKYNWXNXXHWHLL-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-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
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- UTFSEWQOIIZLRH-UHFFFAOYSA-N 1,7-diisocyanatoheptane Chemical compound O=C=NCCCCCCCN=C=O UTFSEWQOIIZLRH-UHFFFAOYSA-N 0.000 description 1
- QUPKOUOXSNGVLB-UHFFFAOYSA-N 1,8-diisocyanatooctane Chemical compound O=C=NCCCCCCCCN=C=O QUPKOUOXSNGVLB-UHFFFAOYSA-N 0.000 description 1
- FJWZMLSQLCKKGV-UHFFFAOYSA-N 1-(2-ethylphenyl)propane-1,1-diamine Chemical compound CCC1=CC=CC=C1C(N)(N)CC FJWZMLSQLCKKGV-UHFFFAOYSA-N 0.000 description 1
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 1
- CVFRFSNPBJUQMG-UHFFFAOYSA-N 2,3-bis(2-hydroxyethyl)benzene-1,4-diol Chemical compound OCCC1=C(O)C=CC(O)=C1CCO CVFRFSNPBJUQMG-UHFFFAOYSA-N 0.000 description 1
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 description 1
- BPRJQFIHEGORJE-UHFFFAOYSA-N 2-(1-hydroxypropan-2-yloxy)propan-1-ol 1-(2-hydroxypropoxy)propan-2-ol Chemical compound CC(O)COCC(C)O.CC(CO)OC(C)CO BPRJQFIHEGORJE-UHFFFAOYSA-N 0.000 description 1
- FEWFXBUNENSNBQ-UHFFFAOYSA-N 2-hydroxyacrylic acid Chemical class OC(=C)C(O)=O FEWFXBUNENSNBQ-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- KMHZPJNVPCAUMN-UHFFFAOYSA-N Erbon Chemical compound CC(Cl)(Cl)C(=O)OCCOC1=CC(Cl)=C(Cl)C=C1Cl KMHZPJNVPCAUMN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000796522 Olene Species 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-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
- 239000013543 active substance Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical compound N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical class CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- GKGXKPRVOZNVPQ-UHFFFAOYSA-N diisocyanatomethylcyclohexane Chemical compound O=C=NC(N=C=O)C1CCCCC1 GKGXKPRVOZNVPQ-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- PYBNTRWJKQJDRE-UHFFFAOYSA-L dodecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O PYBNTRWJKQJDRE-UHFFFAOYSA-L 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-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
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229920000587 hyperbranched polymer Polymers 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 150000002506 iron compounds Chemical class 0.000 description 1
- AQBLLJNPHDIAPN-LNTINUHCSA-K iron(3+);(z)-4-oxopent-2-en-2-olate Chemical compound [Fe+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O AQBLLJNPHDIAPN-LNTINUHCSA-K 0.000 description 1
- HLJDOURGTRAFHE-UHFFFAOYSA-N isocyanic acid;3,5,5-trimethylcyclohex-2-en-1-one Chemical compound N=C=O.N=C=O.CC1=CC(=O)CC(C)(C)C1 HLJDOURGTRAFHE-UHFFFAOYSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 239000007783 nanoporous material Substances 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 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
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000001812 pycnometry Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000000352 supercritical drying Methods 0.000 description 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-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
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
-
- 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
- C08G2110/0066—≥ 150kg/m3
-
- 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
- C08G2110/0091—Aerogels; Xerogels
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005025970A DE102005025970A1 (de) | 2005-06-03 | 2005-06-03 | Poröse Polyisocyanat-Polyadditionsprodukte |
| ES06763378T ES2352108T3 (es) | 2005-06-03 | 2006-05-30 | Productos porosos de poliadición de poliisocianato. |
| JP2008514096A JP5553507B2 (ja) | 2005-06-03 | 2006-05-30 | 多孔質ポリイソシアネート重付加生成物 |
| PCT/EP2006/062728 WO2006128872A1 (de) | 2005-06-03 | 2006-05-30 | Poröse polyisocyanat-polyadditionsprodukte |
| AT06763378T ATE479718T1 (de) | 2005-06-03 | 2006-05-30 | Poröse polyisocyanat-polyadditionsprodukte |
| US11/916,069 US8067480B2 (en) | 2005-06-03 | 2006-05-30 | Porous polyisocyanate polyaddition products |
| EP06763378A EP1896518B1 (de) | 2005-06-03 | 2006-05-30 | Poröse polyisocyanat-polyadditionsprodukte |
| CN2006800189182A CN101184788B (zh) | 2005-06-03 | 2006-05-30 | 多孔聚异氰酸酯加聚产物 |
| DE502006007783T DE502006007783D1 (de) | 2005-06-03 | 2006-05-30 | Poröse polyisocyanat-polyadditionsprodukte |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005025970A DE102005025970A1 (de) | 2005-06-03 | 2005-06-03 | Poröse Polyisocyanat-Polyadditionsprodukte |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102005025970A1 true DE102005025970A1 (de) | 2006-12-07 |
Family
ID=36874341
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102005025970A Withdrawn DE102005025970A1 (de) | 2005-06-03 | 2005-06-03 | Poröse Polyisocyanat-Polyadditionsprodukte |
| DE502006007783T Active DE502006007783D1 (de) | 2005-06-03 | 2006-05-30 | Poröse polyisocyanat-polyadditionsprodukte |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE502006007783T Active DE502006007783D1 (de) | 2005-06-03 | 2006-05-30 | Poröse polyisocyanat-polyadditionsprodukte |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8067480B2 (https=) |
| EP (1) | EP1896518B1 (https=) |
| JP (1) | JP5553507B2 (https=) |
| CN (1) | CN101184788B (https=) |
| AT (1) | ATE479718T1 (https=) |
| DE (2) | DE102005025970A1 (https=) |
| ES (1) | ES2352108T3 (https=) |
| WO (1) | WO2006128872A1 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007065841A1 (de) | 2005-12-09 | 2007-06-14 | Basf Se | Aufzeichnungsmaterialien für ink-jet |
| WO2011045306A1 (de) * | 2009-10-16 | 2011-04-21 | Basf Se | Verfahren zur herstellung einer nanoporösen beschichtung auf polyurethanbasis |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8568888B2 (en) | 2007-03-15 | 2013-10-29 | Nanovere Technologies, Inc. | Dendritic polyurethane coating |
| US8206827B2 (en) * | 2007-03-15 | 2012-06-26 | Nanovere Technologies, Llc | Dendritic polyurethane coating |
| EP2158244B1 (de) * | 2007-05-16 | 2010-10-13 | Basf Se | Xerogele auf basis von aromatischem polyharnstoff |
| WO2009134425A1 (en) | 2008-05-02 | 2009-11-05 | Industrial Science & Technology Network, Inc. | Superinsulation with nanopores |
| DE102009053218A1 (de) | 2009-11-06 | 2011-07-14 | Bayer MaterialScience AG, 51373 | Verfahren zur Herstellung eines Polyurethanschaums mittels über- oder nahekritischen Treibmittels |
| JP5856974B2 (ja) * | 2009-11-25 | 2016-02-10 | ダウ グローバル テクノロジーズ エルエルシー | 高い空隙率を有するナノ多孔質ポリマー発泡体 |
| US8927079B2 (en) | 2012-11-28 | 2015-01-06 | Aerogel Technologies, Llc | Porous polyurethane networks and methods of preparation |
| WO2015074988A1 (en) | 2013-11-22 | 2015-05-28 | Basf Se | Nanoporous composite material with low density comprising hollow particles |
| WO2015193336A1 (en) | 2014-06-20 | 2015-12-23 | Basf Se | Nanoporous carbon foams |
| DE102015215055A1 (de) | 2015-08-06 | 2017-02-09 | Basf Se | Nanoporöses Verbundmaterial enthaltend anorganische Hohlpartikel |
| CA3004784C (en) * | 2015-11-16 | 2024-04-23 | Huntsman International Llc | (super)hydrophobic isocyanate based porous materials |
| CN108285520B (zh) * | 2018-01-29 | 2021-04-06 | 爱彼爱和新材料有限公司 | 一种聚氨酯-聚脲结构互穿气凝胶及其制备方法 |
| EP4190216A4 (en) * | 2020-07-31 | 2024-09-04 | Canon Kabushiki Kaisha | WIPER BLADE FOR CLEANING |
| MX2023006127A (es) * | 2020-12-03 | 2023-06-02 | Huntsman Int Llc | Una composicion de espuma de poliuretano que comprende un compuesto de poliol de poliester aromatico y productos fabricados a partir del mismo. |
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| US3574150A (en) | 1969-05-28 | 1971-04-06 | Atomic Energy Commission | Open-pore polyurethane product |
| US4248975A (en) * | 1978-03-22 | 1981-02-03 | Witco Chemical Corporation | Rigid shrink stable polyurethane foam derived from an adduct of an alkylene oxide having at least three carbon atoms and a polyol having at least four hydroxy groups and blown with a fluorinated-chlorinated alkane |
| US4943597A (en) | 1988-12-07 | 1990-07-24 | The Dow Chemical Company | Polyether polyol formulations for hard CFC replacement by water blowing in rigid polyurethane foams |
| US5104964A (en) * | 1989-08-03 | 1992-04-14 | Idemitsu Petrochemical Co., Ltd. | Branched polycarbonate having branching parameter and degree of branching |
| US5198522A (en) * | 1991-12-19 | 1993-03-30 | Miles Inc. | Reaction injection molding based on diethyl methylene diphenyl diisocyanate |
| US5652278A (en) * | 1993-06-22 | 1997-07-29 | Imperial Chemical Industries Plc | Microvoid polyurethane materials |
| US5478867A (en) | 1993-07-07 | 1995-12-26 | The Dow Chemical Company | Microporous isocyanate-based polymer compositions and method of preparation |
| WO1995003358A1 (en) | 1993-07-22 | 1995-02-02 | Imperial Chemical Industries Plc | Organic aerogels |
| DK0826011T3 (da) | 1995-05-18 | 1999-10-11 | Ici Plc | Organiske aerogeler |
| JPH11509878A (ja) | 1995-05-22 | 1999-08-31 | インペリアル・ケミカル・インダストリーズ・ピーエルシー | 有機エーロゲル |
| KR20010005842A (ko) | 1997-04-01 | 2001-01-15 | 스윈넨 앤 마리 | 폴리이소시아네이트 기재 크세로겔 |
| KR20010005841A (ko) | 1997-04-01 | 2001-01-15 | 스윈넨 앤 마리 | 폴리이소시아네이트 기재 에어로겔 |
| US6162860A (en) * | 1997-11-12 | 2000-12-19 | S. C. Johnson Commercial Markets, Inc. | Solvent based interactive polymeric compositions containing a substantially non-gelled composition |
| WO2000024799A1 (en) | 1998-10-22 | 2000-05-04 | Huntsman International Llc | Insulated bodies |
| JP2001263926A (ja) * | 2000-03-17 | 2001-09-26 | Matsushita Refrig Co Ltd | 有機多孔体の製造方法および断熱パネルと断熱箱体 |
| DE60141502D1 (de) * | 2000-07-28 | 2010-04-22 | Woodbridge Foam Corp | Verbesserte härteeigenschaften aufweisendes geschäumtes auf isocyanat basierendes polymer und verfahren zur herstellung |
| AU8273301A (en) * | 2000-07-28 | 2002-02-13 | Perstorp Ab | Dendritic macromolecule with improved polyether polyol solubility and process for production thereof |
| CA2417545A1 (en) * | 2002-01-28 | 2003-07-28 | Ferdiemar N. Valentin | Foamed isocynate-based polymer having improved hardness and process for production thereof |
| DE10219508A1 (de) | 2002-04-30 | 2003-11-13 | Basf Ag | Verfahren zur Herstellung hochfunktioneller, hyperverzweigter Polyester |
| DE10240817A1 (de) | 2002-08-30 | 2004-03-11 | Basf Ag | Verfahren zur Herstellung hyperverzweigter, wasserlöslicher Polyester |
| DE10353745A1 (de) | 2003-11-17 | 2005-06-23 | Basf Ag | Nanoporöse Polymerschaumstoffe durch Aushärten von Reaktivharzen in Mikroemulsion |
| DE102004014287A1 (de) | 2004-03-22 | 2005-10-06 | Basf Ag | Verfahren zur Herstellung von Polymerschäumen auf Basis von Polykondensations-Reaktivharzen |
| PL1732975T3 (pl) | 2004-03-25 | 2010-11-30 | Basf Se | Nanoporowate polimerowe tworzywa piankowe z wielofazowych mieszanin polimerowych zawierających porofor |
| US8933188B2 (en) * | 2004-11-12 | 2015-01-13 | Henkel US IP LLC | Low misting laminating adhesives |
| DE102005015983A1 (de) | 2005-04-07 | 2006-10-12 | Basf Ag | Nanokomposit-Schaumstoff |
-
2005
- 2005-06-03 DE DE102005025970A patent/DE102005025970A1/de not_active Withdrawn
-
2006
- 2006-05-30 EP EP06763378A patent/EP1896518B1/de not_active Not-in-force
- 2006-05-30 CN CN2006800189182A patent/CN101184788B/zh not_active Expired - Fee Related
- 2006-05-30 WO PCT/EP2006/062728 patent/WO2006128872A1/de not_active Ceased
- 2006-05-30 ES ES06763378T patent/ES2352108T3/es active Active
- 2006-05-30 JP JP2008514096A patent/JP5553507B2/ja not_active Expired - Fee Related
- 2006-05-30 DE DE502006007783T patent/DE502006007783D1/de active Active
- 2006-05-30 US US11/916,069 patent/US8067480B2/en not_active Expired - Fee Related
- 2006-05-30 AT AT06763378T patent/ATE479718T1/de active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007065841A1 (de) | 2005-12-09 | 2007-06-14 | Basf Se | Aufzeichnungsmaterialien für ink-jet |
| WO2011045306A1 (de) * | 2009-10-16 | 2011-04-21 | Basf Se | Verfahren zur herstellung einer nanoporösen beschichtung auf polyurethanbasis |
Also Published As
| Publication number | Publication date |
|---|---|
| JP5553507B2 (ja) | 2014-07-16 |
| US20080188577A1 (en) | 2008-08-07 |
| US8067480B2 (en) | 2011-11-29 |
| DE502006007783D1 (de) | 2010-10-14 |
| JP2008542490A (ja) | 2008-11-27 |
| CN101184788B (zh) | 2010-11-10 |
| CN101184788A (zh) | 2008-05-21 |
| ES2352108T3 (es) | 2011-02-15 |
| EP1896518B1 (de) | 2010-09-01 |
| EP1896518A1 (de) | 2008-03-12 |
| ATE479718T1 (de) | 2010-09-15 |
| WO2006128872A1 (de) | 2006-12-07 |
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