JP2013531110A - 多孔質ポリウレア系材料の製造方法 - Google Patents
多孔質ポリウレア系材料の製造方法 Download PDFInfo
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- JP2013531110A JP2013531110A JP2013517218A JP2013517218A JP2013531110A JP 2013531110 A JP2013531110 A JP 2013531110A JP 2013517218 A JP2013517218 A JP 2013517218A JP 2013517218 A JP2013517218 A JP 2013517218A JP 2013531110 A JP2013531110 A JP 2013531110A
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- Japan
- Prior art keywords
- mass
- component
- gel
- porous material
- diaminodiphenylmethane
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 13
- 239000000463 material Substances 0.000 title description 8
- 229920002396 Polyurea Polymers 0.000 title description 2
- 239000011148 porous material Substances 0.000 claims abstract description 90
- 239000002904 solvent Substances 0.000 claims abstract description 59
- 150000004982 aromatic amines Chemical class 0.000 claims abstract description 49
- 239000012948 isocyanate Substances 0.000 claims abstract description 45
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 33
- 150000001412 amines Chemical class 0.000 claims abstract description 32
- 239000011810 insulating material Substances 0.000 claims abstract description 6
- 239000003054 catalyst Substances 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 238000001035 drying Methods 0.000 claims description 19
- 239000007788 liquid Substances 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 125000000524 functional group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- OMHOXRVODFQGCA-UHFFFAOYSA-N 4-[(4-amino-3,5-dimethylphenyl)methyl]-2,6-dimethylaniline Chemical compound CC1=C(N)C(C)=CC(CC=2C=C(C)C(N)=C(C)C=2)=C1 OMHOXRVODFQGCA-UHFFFAOYSA-N 0.000 claims description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 87
- 239000000499 gel Substances 0.000 description 52
- 239000000203 mixture Substances 0.000 description 50
- 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 34
- 238000006243 chemical reaction Methods 0.000 description 34
- 239000011521 glass Substances 0.000 description 27
- 238000003756 stirring Methods 0.000 description 19
- 238000002156 mixing Methods 0.000 description 17
- -1 trimethylene, tetramethylene, pentamethylene, hexamethylene, hepta Methylene Chemical group 0.000 description 16
- 238000001879 gelation Methods 0.000 description 15
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 15
- 125000003277 amino group Chemical group 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 239000000178 monomer Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical class C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 7
- PVXVWWANJIWJOO-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-N-ethylpropan-2-amine Chemical compound CCNC(C)CC1=CC=C2OCOC2=C1 PVXVWWANJIWJOO-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- QMMZSJPSPRTHGB-UHFFFAOYSA-N MDEA Natural products CC(C)CCCCC=CCC=CC(O)=O QMMZSJPSPRTHGB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 238000005829 trimerization reaction Methods 0.000 description 5
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 4
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 238000000635 electron micrograph Methods 0.000 description 4
- 238000009413 insulation Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000003980 solgel method Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 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 3
- HILAULICMJUOLK-UHFFFAOYSA-N 1,3-diethyl-5-methylbenzene Chemical compound CCC1=CC(C)=CC(CC)=C1 HILAULICMJUOLK-UHFFFAOYSA-N 0.000 description 2
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 2
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
- OMDXZWUHIHTREC-UHFFFAOYSA-N 1-[2-(dimethylamino)ethoxy]ethanol Chemical compound CC(O)OCCN(C)C OMDXZWUHIHTREC-UHFFFAOYSA-N 0.000 description 2
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FTZILAQGHINQQR-UHFFFAOYSA-N 2-Methylpentanal Chemical compound CCCC(C)C=O FTZILAQGHINQQR-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- OHKOAJUTRVTYSW-UHFFFAOYSA-N 2-[(2-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1N OHKOAJUTRVTYSW-UHFFFAOYSA-N 0.000 description 2
- UTNMPUFESIRPQP-UHFFFAOYSA-N 2-[(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC=C1N UTNMPUFESIRPQP-UHFFFAOYSA-N 0.000 description 2
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 2
- OAGGYKVXVKGZOZ-UHFFFAOYSA-N 2-amino-1-(dimethylamino)ethanol Chemical compound CN(C)C(O)CN OAGGYKVXVKGZOZ-UHFFFAOYSA-N 0.000 description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- RQEOBXYYEPMCPJ-UHFFFAOYSA-N 4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N RQEOBXYYEPMCPJ-UHFFFAOYSA-N 0.000 description 2
- JHCBFGGESJQAIQ-UHFFFAOYSA-N 4-[(4-amino-3,5-dimethylcyclohexyl)methyl]-2,6-dimethylcyclohexan-1-amine Chemical compound C1C(C)C(N)C(C)CC1CC1CC(C)C(N)C(C)C1 JHCBFGGESJQAIQ-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- HYTRYEXINDDXJK-UHFFFAOYSA-N Ethyl isopropyl ketone Chemical compound CCC(=O)C(C)C HYTRYEXINDDXJK-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 150000004984 aromatic diamines Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 230000002902 bimodal effect Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 150000001983 dialkylethers Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000010191 image analysis Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical class OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 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 2
- 150000004998 toluenediamines Chemical class 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 description 1
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 1
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical group O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- RQUBQBFVDOLUKC-UHFFFAOYSA-N 1-ethoxy-2-methylpropane Chemical compound CCOCC(C)C RQUBQBFVDOLUKC-UHFFFAOYSA-N 0.000 description 1
- PZHIWRCQKBBTOW-UHFFFAOYSA-N 1-ethoxybutane Chemical compound CCCCOCC PZHIWRCQKBBTOW-UHFFFAOYSA-N 0.000 description 1
- NVJUHMXYKCUMQA-UHFFFAOYSA-N 1-ethoxypropane Chemical compound CCCOCC NVJUHMXYKCUMQA-UHFFFAOYSA-N 0.000 description 1
- JIABEENURMZTTI-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatophenyl)methyl]benzene Chemical compound O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O JIABEENURMZTTI-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
- ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical compound COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 description 1
- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 1
- JIEJJGMNDWIGBJ-UHFFFAOYSA-N 1-propan-2-yloxypropane Chemical compound CCCOC(C)C JIEJJGMNDWIGBJ-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
- DYVJZCIYRQUXBA-UHFFFAOYSA-N 2,5-dimethyl-3,4-dihydropyran-2-carbaldehyde Chemical compound CC1=COC(C)(C=O)CC1 DYVJZCIYRQUXBA-UHFFFAOYSA-N 0.000 description 1
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
- PBUMTLOEAITQSM-UHFFFAOYSA-N 2-(3-aminopentan-3-yl)aniline Chemical compound CCC(N)(CC)C1=CC=CC=C1N PBUMTLOEAITQSM-UHFFFAOYSA-N 0.000 description 1
- UNNGUFMVYQJGTD-UHFFFAOYSA-N 2-Ethylbutanal Chemical compound CCC(CC)C=O UNNGUFMVYQJGTD-UHFFFAOYSA-N 0.000 description 1
- IEMMBWWQXVXBEU-UHFFFAOYSA-N 2-acetylfuran Chemical compound CC(=O)C1=CC=CO1 IEMMBWWQXVXBEU-UHFFFAOYSA-N 0.000 description 1
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 description 1
- RMGHERXMTMUMMV-UHFFFAOYSA-N 2-methoxypropane Chemical compound COC(C)C RMGHERXMTMUMMV-UHFFFAOYSA-N 0.000 description 1
- NPWYTMFWRRIFLK-UHFFFAOYSA-N 3,4-dihydro-2h-pyran-2-carbaldehyde Chemical compound O=CC1CCC=CO1 NPWYTMFWRRIFLK-UHFFFAOYSA-N 0.000 description 1
- SHXWCVYOXRDMCX-UHFFFAOYSA-N 3,4-methylenedioxymethamphetamine Chemical compound CNC(C)CC1=CC=C2OCOC2=C1 SHXWCVYOXRDMCX-UHFFFAOYSA-N 0.000 description 1
- UXECSYGSVNRHFN-UHFFFAOYSA-M 3-hydroxypropyl(trimethyl)azanium;formate Chemical compound [O-]C=O.C[N+](C)(C)CCCO UXECSYGSVNRHFN-UHFFFAOYSA-M 0.000 description 1
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 1
- ZMMOYIXZGHJMNI-UHFFFAOYSA-N 3-oxopropanenitrile Chemical compound O=CCC#N ZMMOYIXZGHJMNI-UHFFFAOYSA-N 0.000 description 1
- QJMYXHKGEGNLED-UHFFFAOYSA-N 5-(2-hydroxyethylamino)-1h-pyrimidine-2,4-dione Chemical compound OCCNC1=CNC(=O)NC1=O QJMYXHKGEGNLED-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical class [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- BRDWIEOJOWJCLU-LTGWCKQJSA-N GS-441524 Chemical compound C=1C=C2C(N)=NC=NN2C=1[C@]1(C#N)O[C@H](CO)[C@@H](O)[C@H]1O BRDWIEOJOWJCLU-LTGWCKQJSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BKAKFCXOCHNIIP-UHFFFAOYSA-N N=C=O.N=C=O.CC1=CC=CC(C=2C=C(C)C=CC=2)=C1 Chemical compound N=C=O.N=C=O.CC1=CC=CC(C=2C=C(C)C=CC=2)=C1 BKAKFCXOCHNIIP-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 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
- 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
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000004964 aerogel Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- QJSCFMXSIVOKPS-UHFFFAOYSA-N azane ethyl hexanoate Chemical compound N.CCCCCC(=O)OCC QJSCFMXSIVOKPS-UHFFFAOYSA-N 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- DCFDVJPDXYGCOK-UHFFFAOYSA-N cyclohex-3-ene-1-carbaldehyde Chemical compound O=CC1CCC=CC1 DCFDVJPDXYGCOK-UHFFFAOYSA-N 0.000 description 1
- XXKOQQBKBHUATC-UHFFFAOYSA-N cyclohexylmethylcyclohexane Chemical compound C1CCCCC1CC1CCCCC1 XXKOQQBKBHUATC-UHFFFAOYSA-N 0.000 description 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VNKYTQGIUYNRMY-UHFFFAOYSA-N methoxypropane Chemical compound CCCOC VNKYTQGIUYNRMY-UHFFFAOYSA-N 0.000 description 1
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- QFAWAPOFKBIROP-UHFFFAOYSA-N n-benzhydrylbutan-2-amine Chemical group C=1C=CC=CC=1C(NC(C)CC)C1=CC=CC=C1 QFAWAPOFKBIROP-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 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
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- GCHCGDFZHOEXMP-UHFFFAOYSA-L potassium adipate Chemical compound [K+].[K+].[O-]C(=O)CCCCC([O-])=O GCHCGDFZHOEXMP-UHFFFAOYSA-L 0.000 description 1
- 239000001608 potassium adipate Substances 0.000 description 1
- 235000011051 potassium adipate Nutrition 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 description 1
- WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000000352 supercritical drying Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009044 synergistic interaction Effects 0.000 description 1
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides 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
- 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
- 125000005628 tolylene group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-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
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3237—Polyamines aromatic
- C08G18/3243—Polyamines aromatic containing two or more aromatic rings
-
- 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
-
- 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
- C08J9/28—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a liquid phase from a macromolecular composition or article, e.g. drying of coagulum
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/02—Polyureas
-
- 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
-
- 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
- C08G2330/00—Thermal insulation material
- C08G2330/50—Evacuated open-celled polymer material
-
- 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
- C08J2375/02—Polyureas
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- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本発明はまた、このようにして得られる多孔質材料と該多孔質材料の絶縁材料としてのあるいは真空絶縁パネル中での利用に関する。
Description
ただし、
−一般式Iの化合物が少なくとも2個の一級アミノ基を持ち、Q1とQ3とQ5の少なくとも一つが一級アミノ基であり、Q1’とQ3’とQ5’の少なくとも一つが一級アミノ基あり、また
−Q2、Q4、Q2’、及びQ4’は、一般式Iの化合物が、芳香族環に結合している少なくとも一個の一級アミノ基をα位に有する1〜12個の炭素原子をもち、少なくとも一つの直鎖又は分岐鎖のアルキル基(他の官能基を生じていても良い)を有するように選択され、
必要なら、少なくとも一種の、一般式Iのアミン(a2−s)とは異なる他の多官能性芳香族アミン(a2−u)、および
(a3)水
を溶媒(C)の存在下で、また必要なら少なくとも一種の触媒(a4)の存在下で反応させて本発明の多孔質材料を形成することからなる。
本発明の方法では、成分(a1)として少なくとも一種の多官能性イソシアネートが反応させられる。
i)トリレンジイソシアネート(TDI)系の多官能性イソシアネート、特に2,4−TDIまたは2,6−TDI、または2,4−TDIと2,6−TDIの混合物;
ii)ジフェニルメタンジイソシアネート(MDI)系の多官能性イソシアネート、特に2,2’−MDIまたは2,4’−MDIまたは4,4’−MDIまたはオリゴマー状MDI(ポリフェニルポリメチレンイソシアネートとも呼ばれる)、または上記のジフェニルメタンジイソシアネートの二つまたは三つの混合物、またはMDIの製造の際に得られる粗製MDI、または少なくとも一種のオリゴマー状MDIと少なくとも一種の上記の低分子量MDI誘導体の混合物;
iii)実施様態i)の少なくとも一種の芳香族イソシアネートと実施様態ii)の少なくとも一種の芳香族イソシアネートの混合物。多官能性イソシアネートとしては、オリゴマー状のジフェニルメタンジイソシアネートが特に好ましい。オリゴマー状ジフェニルメタンジイソシアネート(以下、オリゴマー状MDIと称す)は、単独のオリゴマー状縮合生成物または複数のオリゴマー状縮合生成物の混合物であり、したがってジフェニルメタンジイソシアネート(MDI)の誘導体である。これらの多官能性イソシアネートは、好ましくはモノマー状芳香族ジイソシアネートとオリゴマー状MDIの混合物からなっていてもよい。
−一般式Iの化合物が少なくとも2個の一級アミノ基を含み、Q1とQ3とQ5の少なくとも一つが一級アミノ基であり、Q1’とQ3’とQ5’の少なくとも一つが一級アミノ基であり、
−Q2とQ4、Q2’,Q4’は、一般式Iの化合物が、芳香族環に結合している少なくとも一個の一級アミノ基をα位に有する1〜12個の炭素原子をもち、少なくとも一つの直鎖又は分岐鎖のアルキル基(他の官能基を生じていても良い)を有するように選択され、
必要なら少なくとも一種の、一般式Iのアミン(a2−s)とは異なる他の多官能性芳香族アミン(a2−u)が、成分(a2)として反応させられる。
本発明の方法は、成分(a4)としての少なくとも一種の触媒の存在下で行われることが好ましい。
本発明によれば、この反応が溶媒(C)の存在下で起こる。
ある好ましい実施様態においては、本発明の方法は少なくとも以下の工程を含む:
(a)上述の成分(a1)と(a2)と(a3)と溶媒(C)を供給する工程、
(b)溶媒(C)の存在下での成分(a1)と(a2)と(a3)の反応でゲルを形成する工程と
(c)前工程で得られたゲルを乾燥する工程。
本発明によれば、成分(a1)と(a2)と(a3)と溶媒(C)が工程(a)で提供される。
本発明によれば、工程(b)で、溶媒(C)の存在下で成分(a1)と(a2)の反応が起こりゲルを形成する。したがって、本発明の方法の工程(b)では、成分(a1)が一部水と反応して少なくとも一種の多官能性アミンを与え、この多官能性アミンが多官能性イソシアネートとゲル化反応してゲルを与える。
本発明によれば、工程(c)で、前工程で得られたゲルを乾燥する。
本発明はまた、本発明の方法で得ることのできる多孔質材料を提供する。
熱伝導率λは、DIN−EN−12667によりヘスト社の板装置(ラムダコントロールA50)を用いて決定した。
オリゴマー状MDI(ルプラネートRM200):ASTM−D5155−96AによるNCO含量:30.9g/100g、官能価:約3、DIN−53018による粘度:25℃で2100mPa・s(以降、「化合物M200」と称す)
オリゴマー状MDI(ルプラネートRM50):ASTM−D5155−96AによるNCO含量:31.5g/100g、官能価:約2.8〜2.9、DIN−53018による粘度:25℃で550mPa・s(以降、「化合物M200」と称す)
3,3’,5,5’−テトラエチル−4,4’−ジアミノジフェニルメタン(以下、「MDEA」);
3,3’,5,5’−テトラメチル−4,4’−ジアミノジフェニルメタン(以下、「MDMA」)
エタキュアR100、アルベマール社製、特に3,5−ジエチルトルエン−2,4−ジアミンと3,5−ジエチルトルエン−2,6−ジアミンを含む芳香族ジアミン混合物;ユニリンクR4200、UOP社製、4,4’−ビス(sec−ブチルアミノ)ジフェニルメタン構造を持つ芳香族ジアミン;
3,3’,5,5’−テトラメチル−4,4’−ジアミノジシクロヘキシルメタン;
4,4’−ジアミノジフェニルメタン
トリエタノールアミン;トリエチレンジアミン(IUPAC:1,4−ジアザビシクロ[2.2.2]オクタン);
N,N−ジメチルシクロヘキシルアミン
ガラスビーカー中で56gの化合物M50を、撹拌下で20℃で210gのアセトンに溶解した。第二のガラスビーカー中で4gの化合物MDEAと8gの水を210gのアセトンに溶解した。工程(a)からのこれら二つの溶液を撹拌下で混合した。これにより透明な低粘度混合物を得た。この混合物を24時間静置して硬化させた。次いでこのゲルをガラスビーカーから取り出し、液体(アセトン)を20℃で7日間乾燥させて除いた。
ガラスビーカー中で60gの化合物M200を、撹拌下で20℃で210gのアセトンに溶解した。第二のガラスビーカー中で8gの化合物MDEAと8gの水を210gのアセトンに溶解した。工程(a)からのこれら二つの溶液を撹拌下で混合した。これにより透明な低粘度混合物を得た。この混合物を24時間静置して硬化させた。次いでこのゲルをガラスビーカーから取り出し、液体(アセトン)を20℃で7日間乾燥させて除いた。電子顕微鏡写真は、平均孔径が約1μmであることを示した。
ガラスビーカー中で70gの化合物M50を、撹拌下で20℃で210gのアセトンに溶解した。第二のガラスビーカー中で4gの化合物MDEAと2gのトリエタノールアミンと8gの水を210gのアセトンに溶解した。工程(a)からのこれら二つの溶液を撹拌下で混合した。これにより透明な低粘度混合物を得た。この混合物を24時間静置して硬化させた。次いでこのゲルをガラスビーカーから取り出し、液体(アセトン)を20℃で7日間乾燥させて除いた。
ガラスビーカー中で56gの化合物M50を、撹拌下で20℃で210gのアセトンに溶解した。第二のガラスビーカー中で4gの化合物MDEAと0.5gのトリエチレンジアミンと8gの水を210gのアセトンに溶解した。工程(a)からのこれら二つの溶液を撹拌下で混合した。これにより透明な低粘度混合物を得た。この混合物を24時間静置して硬化させた。次いでこのゲルをガラスビーカーから取り出し、液体(アセトン)を20℃で7日間乾燥させて除いた。
ガラスビーカー中で70gの化合物M50を、撹拌下で20℃で210gのアセトンに溶解した。第二のガラスビーカー中で4gの化合物MDEAと2gのN,N−ジメチルシクロヘキシルアミンと8gの水を210gのアセトンに溶解した。工程(a)からのこれら二つの溶液を撹拌下で混合した。これにより透明な低粘度混合物を得た。この混合物を24時間静置して硬化させた。次いでこのゲルをガラスビーカーから取り出し、液体(アセトン)を20℃で7日間乾燥させて除いた。
ガラスビーカー中で、3gの化合物M200を、撹拌下で20℃で10.5gのアセトンに溶解した。第二のガラスビーカー中で0.1gの化合物エタキュアR100と0.5gの水を11gのアセトンに溶解した。工程(a)からのこれら二つの溶液を撹拌下で混合した。これにより透明な低粘度混合物を得た。この混合物を24時間静置して硬化させた。次いでこのゲルをガラスビーカーから取り出し、液体(アセトン)を20℃で7日間乾燥させて除いた。
ガラスビーカー中で3gの化合物M200を、撹拌下で20℃で10.5gのアセトンに溶解した。第二のガラスビーカー中で0.1gのユニリンクR4200と0.5gの水を11gのアセトンに溶解した。工程(a)からのこれら二つの溶液を撹拌下で混合した。これにより透明な低粘度混合物を得た。この混合物を24時間静置して硬化させた。次いでこのゲルをガラスビーカーから取り出し、液体(アセトン)を20℃で7日間乾燥させて除いた。
ガラスビーカー中で3gの化合物M200を、撹拌下で20℃で10.5gのアセトンに溶解した。第二のガラスビーカー中で0.1gの化合物3,3’,5,5’テトラメチル−4,4’−ジアミノジシクロヘキシルメタンと0.5gの水を11gのアセトンに溶解した。工程(a)からのこれら二つの溶液を撹拌下で混合した。これにより透明な低粘度混合物を得た。この混合物を24時間静置して硬化させた。次いでこのゲルをガラスビーカーから取り出し、液体(アセトン)を20℃で7日間乾燥させて除いた。
ガラスビーカー中で3gの化合物M200を、撹拌下で20℃で10.5gのアセトンに溶解した。第二のガラスビーカー中で0.1gの化合物4,4’−ジアミノジフェニルメタンと0.5gの水を11gのアセトンに溶解した。工程(a)からのこれら二つの溶液を撹拌下で混合した。これにより透明な低粘度混合物を得た。この混合物を24時間静置して硬化させた。次いでこのゲルをガラスビーカーから取り出し、液体(アセトン)を20℃で7日間乾燥させて除いた。沈殿物のみが形成され安定なゲルはできなかった。
Claims (16)
- 多孔質材料の製造方法であって、
(a1)少なくとも一種の多官能性イソシアネートと、
(a2)少なくとも一種の、一般式Iをもつ多官能性置換芳香族アミン(a2−s):
−一般式Iの化合物が少なくとも2個の一級アミノ基を含み、Q1、Q3、及びQ5の少なくとも一つが一級アミノ基であり、Q1’、Q3’、及びQ5’の少なくとも一つが一級アミノ基であり、
−Q2、Q4、Q2’、及びQ4’は、一般式Iの化合物が、芳香族環に結合している少なくとも一個の一級アミノ基をα位に有する1〜12個の炭素原子をもち、少なくとも一つの直鎖又は分岐鎖のアルキル基(他の官能基を生じていても良い)を有するように選択され、
任意に、
少なくとも一種の上記一般式Iをもつアミン類(a2−s)とは異なる他の多官能性芳香族アミン(a2−u)と、
(a3)水と、を
溶媒(C)の存在下で、また必要なら少なくとも一種の触媒(a4)の存在下で反応させる製造方法。 - Q2、Q4、Q2’、及びQ4’は、
置換芳香族アミン(a2−s)が、それぞれ、1〜12個の炭素原子のα位にある直鎖又は分岐鎖アルキル基(他の官能基を生じていても良い)を有する少なくとも2個の一級アミノ基を持つように選ばれる請求項1に記載の方法。 - アミン成分(a2)が、3,3’,5,5’−テトラアルキル−4,4’−ジアミノジフェニルメタンと3,3’,5,5’−テトラアルキル−2,2’−ジアミノジフェニルメタン、3,3’,5,5’−テトラアルキル−2,4’−ジアミノジフェニルメタン(式中、3と3’と5と5’位置にあるアルキル基は、同一であっても異なっていてもよく、1〜12個の炭素原子をもち他の官能基を有していてもよい直鎖又は分岐鎖のアルキル基から独立して選ばれる)からなる群から選ばれる少なくとも一種の化合物(a2−s)を含む請求項1または2に記載の方法。
- 一般式Iの多官能性芳香族アミン(a2−s)のアルキル基が、メチルとエチル、n−プロピル、イソプロピル、n−ブチル、sec−ブチル、tert−ブチルから選ばれる請求項1〜3のいずれか一項に記載の方法。
- 一般式Iの多官能性芳香族アミン(a2−s)が、3,3’,5,5’−テトラアルキル−4,4’−ジアミノジフェニルメタンであり、好ましくは3,3’,5,5’−テトラエチル−4,4’−ジアミノジフェニルメタン及び/又は3,3’,5,5’−テトラメチル−4,4’−ジアミノジフェニルメタンである請求項1〜4のいずれか一項に記載の方法。
- 用いる成分(a1)の量が、成分(a1)と(a2)と(a3)の総質量の100質量%に対して40〜99.8質量%であり、特に55〜99.3質量%である請求項1〜5のいずれか一項に記載の方法。
- 用いる成分(a2)の量が、成分(a1)と(a2)と(a3)の総質量の100質量%に対して0.1〜30質量%であり、成分(a1)の量が40〜99.8質量%であり、成分(a3)の量が0.1〜30質量%である請求項1〜6のいずれか一項に記載の方法。
- 成分(a2)が一般式Iの(a2−s)型の化合物のみからなる請求項1〜7のいずれか一項に記載の方法。
- 触媒(a4)の存在下で行われる請求項1〜8のいずれか一項に記載の方法。
- 触媒(a4)としての少なくとも一種の第三級アミンの存在下で行われる請求項1〜9のいずれか一項に記載の方法。
- a)請求項1〜8に規定する成分(a1)と(a2)と(a3)と(C)を提供し、
b)溶媒(C)の存在下で成分(a1)と(a2)と(a3)を反応させてゲルを形成し、
c)前工程で得られるゲルを乾燥する
ことからなる請求項1〜10のいずれか一項に記載の方法。 - 成分(a1)と(a2)が、それぞれ一部量の溶媒(C)中に入れられて別個に提供される請求項11に記載の方法。
- 得られるゲルの乾燥が、ゲル中に含まれる液体の臨界温度と臨界圧力未満の温度と圧力でゲル中に含まれる液体をガス状に変換して行われる請求項11または12に記載の方法。
- 得られるゲルの乾燥が超臨界条件下で行われる請求項11または12に記載の方法。
- 請求項1〜14のいずれか一項に記載の方法により得られる多孔性材料。
- 請求項15に記載の多孔質材料の絶縁材料としての、あるいは真空絶縁パネル用の利用。
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JP2022517823A (ja) | 2019-01-17 | 2022-03-10 | ビーエーエスエフ ソシエタス・ヨーロピア | 多孔質材料を製造する方法 |
EP3831869B1 (en) | 2019-12-05 | 2024-03-06 | Basf Se | Composite polystyrene foam molding with low thermal conductivity |
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AU5862099A (en) | 1998-10-22 | 2000-05-15 | Huntsman Ici Chemicals Llc | Insulated bodies |
EP1178063A1 (en) * | 2000-08-01 | 2002-02-06 | Huntsman International Llc | Process for preparing a polyurethane material |
CN101679584B (zh) | 2007-05-16 | 2012-02-08 | 巴斯夫欧洲公司 | 由芳香族聚脲制备的干凝胶 |
EP2185620B1 (de) | 2007-08-28 | 2011-04-13 | Basf Se | Xerogele auf basis von polyharnstoff |
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US5478867A (en) * | 1993-07-07 | 1995-12-26 | The Dow Chemical Company | Microporous isocyanate-based polymer compositions and method of preparation |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2015532316A (ja) * | 2012-09-27 | 2015-11-09 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 多孔質材料の製造方法、多孔質材料及びその使用方法 |
JP2016520143A (ja) * | 2013-05-24 | 2016-07-11 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 多孔性材料の製造方法 |
JP2017512864A (ja) * | 2014-03-24 | 2017-05-25 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 多孔性材料の製造方法 |
JP2017512865A (ja) * | 2014-03-24 | 2017-05-25 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 多孔性材料の製造方法 |
KR20170033380A (ko) * | 2014-07-18 | 2017-03-24 | 바스프 에스이 | 다공성 재료의 제조 방법 |
JP2018502174A (ja) * | 2014-07-18 | 2018-01-25 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 多孔性材料の製造方法 |
KR102461563B1 (ko) | 2014-07-18 | 2022-11-01 | 에어로젤-잇 게엠베하 | 다공성 재료의 제조 방법 |
CN108475718A (zh) * | 2015-10-27 | 2018-08-31 | 韩国科学技术院 | 柔性热电元件及其制造方法 |
Also Published As
Publication number | Publication date |
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PT2585508E (pt) | 2014-09-10 |
AU2011273624B2 (en) | 2015-04-16 |
KR20130124287A (ko) | 2013-11-13 |
EP2585508A1 (de) | 2013-05-01 |
RU2565421C2 (ru) | 2015-10-20 |
CA2801521A1 (en) | 2012-01-05 |
JP5882314B2 (ja) | 2016-03-09 |
EP2585508B1 (de) | 2014-07-16 |
EP2399945A1 (de) | 2011-12-28 |
WO2012000917A1 (de) | 2012-01-05 |
KR101870463B1 (ko) | 2018-06-22 |
ES2503192T3 (es) | 2014-10-06 |
PL2585508T3 (pl) | 2014-12-31 |
AU2011273624A1 (en) | 2013-01-10 |
CN102958968B (zh) | 2014-12-24 |
RU2013103402A (ru) | 2014-08-10 |
MX2012014924A (es) | 2013-02-12 |
CN102958968A (zh) | 2013-03-06 |
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