JP5925813B2 - ポリウレア系難燃性多孔質材料の製造方法 - Google Patents
ポリウレア系難燃性多孔質材料の製造方法 Download PDFInfo
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- JP5925813B2 JP5925813B2 JP2013558376A JP2013558376A JP5925813B2 JP 5925813 B2 JP5925813 B2 JP 5925813B2 JP 2013558376 A JP2013558376 A JP 2013558376A JP 2013558376 A JP2013558376 A JP 2013558376A JP 5925813 B2 JP5925813 B2 JP 5925813B2
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- 239000011148 porous material Substances 0.000 title claims description 100
- 239000003063 flame retardant Substances 0.000 title claims description 23
- 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 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title description 7
- 229920002396 Polyurea Polymers 0.000 title 1
- 239000002904 solvent Substances 0.000 claims description 60
- 238000000034 method Methods 0.000 claims description 58
- 239000003054 catalyst Substances 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 44
- 150000002513 isocyanates Chemical class 0.000 claims description 42
- 239000012948 isocyanate Substances 0.000 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 37
- 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 claims description 36
- 150000004982 aromatic amines Chemical class 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000000524 functional group Chemical group 0.000 claims description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 239000003960 organic solvent Substances 0.000 claims description 13
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 150000003007 phosphonic acid derivatives Chemical class 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 238000009413 insulation Methods 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 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 claims description 2
- 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 claims description 2
- OHKOAJUTRVTYSW-UHFFFAOYSA-N 2-[(2-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1N OHKOAJUTRVTYSW-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 238000010276 construction Methods 0.000 claims 1
- 239000000499 gel Substances 0.000 description 47
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 41
- -1 2-methylpentamethylene Chemical group 0.000 description 20
- 150000001412 amines Chemical class 0.000 description 18
- 238000001035 drying Methods 0.000 description 18
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- 125000003277 amino group Chemical group 0.000 description 12
- 239000011521 glass Substances 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 150000002576 ketones Chemical class 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 239000000178 monomer Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 238000001879 gelation Methods 0.000 description 8
- 150000002894 organic compounds Chemical group 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229940042400 direct acting antivirals phosphonic acid derivative Drugs 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000005829 trimerization reaction Methods 0.000 description 6
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 4
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 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
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000007795 chemical reaction product 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
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000011810 insulating material Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 3
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000003980 solgel method Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 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
- AATNZNJRDOVKDD-UHFFFAOYSA-N 1-[ethoxy(ethyl)phosphoryl]oxyethane Chemical compound CCOP(=O)(CC)OCC AATNZNJRDOVKDD-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
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-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
- RBOSLVRUYBQPOX-UHFFFAOYSA-N 3-[3-hydroxypropyl(2-methylpropyl)phosphoryl]propan-1-ol Chemical compound OCCCP(=O)(CC(C)C)CCCO RBOSLVRUYBQPOX-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 2
- OZEIKKSJNYAJPR-UHFFFAOYSA-N [hydroxymethyl(2-methylpropyl)phosphoryl]methanol Chemical compound CC(C)CP(=O)(CO)CO OZEIKKSJNYAJPR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004964 aerogel Substances 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004132 cross linking Methods 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
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 2
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group 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
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 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
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 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
- 235000021317 phosphate Nutrition 0.000 description 2
- 238000002459 porosimetry Methods 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000000352 supercritical drying Methods 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 2
- 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 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
- ZMBHCYHQLYEYDV-UHFFFAOYSA-N trioctylphosphine oxide Chemical compound CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC ZMBHCYHQLYEYDV-UHFFFAOYSA-N 0.000 description 2
- XMNDMAQKWSQVOV-UHFFFAOYSA-N (2-methylphenyl) diphenyl phosphate Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 XMNDMAQKWSQVOV-UHFFFAOYSA-N 0.000 description 1
- OWICEWMBIBPFAH-UHFFFAOYSA-N (3-diphenoxyphosphoryloxyphenyl) diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=C(OP(=O)(OC=2C=CC=CC=2)OC=2C=CC=CC=2)C=CC=1)(=O)OC1=CC=CC=C1 OWICEWMBIBPFAH-UHFFFAOYSA-N 0.000 description 1
- 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
- AQPHBYQUCKHJLT-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-(2,3,4,5,6-pentabromophenyl)benzene Chemical group BrC1=C(Br)C(Br)=C(Br)C(Br)=C1C1=C(Br)C(Br)=C(Br)C(Br)=C1Br AQPHBYQUCKHJLT-UHFFFAOYSA-N 0.000 description 1
- NDRKXFLZSRHAJE-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-(2,3,4-tribromophenyl)benzene Chemical group BrC1=C(Br)C(Br)=CC=C1C1=C(Br)C(Br)=C(Br)C(Br)=C1Br NDRKXFLZSRHAJE-UHFFFAOYSA-N 0.000 description 1
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- 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
- 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
- 238000005057 refrigeration Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000000779 smoke 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
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010998 test method Methods 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
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- KVMPUXDNESXNOH-UHFFFAOYSA-N tris(1-chloropropan-2-yl) phosphate Chemical compound ClCC(C)OP(=O)(OC(C)CCl)OC(C)CCl KVMPUXDNESXNOH-UHFFFAOYSA-N 0.000 description 1
- GTRSAMFYSUBAGN-UHFFFAOYSA-N tris(2-chloropropyl) phosphate Chemical compound CC(Cl)COP(=O)(OCC(C)Cl)OCC(C)Cl GTRSAMFYSUBAGN-UHFFFAOYSA-N 0.000 description 1
- LIPMRGQQBZJCTM-UHFFFAOYSA-N tris(2-propan-2-ylphenyl) phosphate Chemical compound CC(C)C1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C(C)C)OC1=CC=CC=C1C(C)C LIPMRGQQBZJCTM-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
- 239000003643 water by type Substances 0.000 description 1
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- C08G18/3802—Low-molecular-weight compounds having heteroatoms other than oxygen having halogens
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Description
本発明の方法は、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を反応させる。
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種または三種の混合物、またはMDIの製造過程で製造される粗製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)のような少なくとも一種の芳香族イソシアネートと実施様態II)のような少なくとも一種の芳香族イソシアネートの混合物。
本発明の成分(a2)は、少なくとも一種の多官能性芳香族アミンである。
式中、R1とR2は、同じであっても異なっていてもよく、相互に独立して、水素と、1〜6個の炭素原子をもつ直鎖又は分岐鎖のアルキル基から選ばれ、Q1〜Q5とQ1’〜Q5’のすべての置換基は、同じであっても異なっていてもよく、相互に独立して、水素と、一級アミノ基、1〜12個の炭素原子を持つ直鎖又は分岐鎖のアルキル基から選ばれ、これらのアルキル基はさらに官能基を持つことができる。ただし、一般式Iの化合物は、少なくとも二個の一級アミノ基をもち、Q1とQ3とQ5の少なくとも一つは一級アミノ基であり、Q1’とQ3’とQ5’の少なくとも一つは一級アミノ基である。
上記範囲内での水の好ましい量は、触媒(a5)が使用されるかどうかにより決まる。
本発明における成分(a1)と(a2)の反応は、少なくとも一種の成分(a4)としての有機難燃剤の存在下で行われる。
ある第一の好ましい実施様態では、本発明の方法を、少なくとも一種の成分(a5)の触媒の存在下で行うことが好ましい。
本発明の反応は、溶媒の存在下で進行する。
本発明の工程(b)では、前工程で得られたゲルから有機溶媒を除いて乾燥させ、有機多孔質材料を得る。
本発明はまた、本発明の方法で得られる多孔質材料を提供する。
試料の気孔体積(ml/g)と材料の平均孔径は、室温でDIN66133(1993)に応じて水銀ポロシメトリーで測定した。本発明の目的では、平均孔径は平均気孔径と同じである。体積平均気孔径は、上記の規格で求めた孔径分布から計算により求めた。
成分a1:
オリゴマー状MDI(ルプラナート(登録商標)M50)、ASTM−D5155−96AによるNCO含量:31.5g/100g、官能価:2.8〜2.9の範囲、DIN53018による粘度:550mPa・s(25℃)(以下、「化合物M50」)
成分a2:
オリゴマー状ジアミノジフェニルメタン、DIN53018での粘度:2710mPa・s(50℃)、官能価:約2.4、アミノ基含量:9.93mmol/g(以下、「PMDA」)
成分a3:
エキソリット(登録商標)OP560
PHT−4−ジオールTM、ケムチュラ社製:
アンチブレーズ(登録商標)V490、アルベマール社製:
20℃、撹拌下で、ガラスビーカー中で10.5gのアセトンに2.0gの化合物M50を溶解した。第二のガラスビーカー中で、1.3gのPMDAと0.5gのエキソリット(登録商標)OP560を、11gのアセトンに溶解した。工程(a)の二つの溶液を混合した。この結果、透明な低粘度混合物を得た。この混合物を室温で24時間放置して硬化させた。次いでゲルをガラスビーカーから取り出し、その液体(アセトン)を20℃で7日間乾燥させて除いた。
20℃、撹拌下でガラスビーカー中で2.0gの化合物M50を10.5gのアセトンに溶解した。第二のガラスビーカー中で1.3gのPMDAと0.5gのPHT−4−ジオールTMを11gのアセトンに溶解した。工程(a)の二つの溶液を混合した。この結果、透明な低粘度混合物を得た。この混合物を室温で24時間放置して硬化させた。次いでゲルをガラスビーカーから取り出し、その液体(アセトン)を20℃で7日間乾燥させて除いた。
20℃、撹拌下で、ガラスビーカー中で2.0gの化合物M50を10.5gのアセトンに溶解した。第二のガラスビーカー中で、1.3gのPMDAと0.5gのアルベマール社製アンチブレーズ(登録商標)V490を11gのアセトンに溶解した。工程(a)の二つの溶液を混合した。この結果、透明な低粘度混合物を得た。この混合物を室温で24時間放置して硬化させた。次いでゲルをガラスビーカーから取り出し、その液体(アセトン)を20℃で7日間乾燥させて除いた。
20℃、撹拌下で、ガラスビーカー中で2.4gの化合物M50を10.5gのアセトンに溶解した。第二のガラスビーカー中で、1.3gの化合物PMDAを11gのアセトンに溶解した。工程(a)の二つの溶液を混合した。この結果、透明な低粘度混合物を得た。この混合物を室温で24時間放置して硬化させた。次いでゲルをガラスビーカーから取り出し、その液体(アセトン)を20℃で7日間乾燥させて除いた。
Claims (23)
- (a)少なくとも一種の多官能性イソシアネート(a1)と少なくとも一種の多官能性芳香族アミン(a2)とを、有機溶媒中で、必要なら成分(a3)としての水の存在下で、また必要なら少なくとも一種の触媒(a5)の存在下で反応させる工程と、続く
(b)該有機溶媒を除いて有機多孔質材料を得る工程と
を含み、
工程(a)が成分(a4)としての少なくとも一種の有機難燃剤の存在下で行われ、この難燃剤が前記溶媒に可溶である多孔質材料の製造方法。 - 成分(a4)の難燃剤が、リン及び/又はハロゲンを含む化合物である請求項1に記載の方法。
- 成分(a4)の使用量が、成分(a1)〜(a4)の総質量100質量%に対して0.1〜25質量%である請求項1または2に記載の方法。
- 成分(a4)が、多臭素化化合物と有機リン化合物からなる群から選ばれる少なくとも一種の難燃剤を含む請求項1〜3のいずれか一項に記載の方法。
- 成分(a4)が少なくとも一種の有機リン酸誘導体を含む請求項1〜4のいずれか一項に記載の方法。
- 成分(a4)が少なくとも一種の有機ホスホン酸誘導体を含む請求項1〜5のいずれか一項に記載の方法。
- 成分(a4)が少なくとも一種の有機ホスフィン酸誘導体を含む請求項1〜6のいずれか一項に記載の方法。
- 成分(a4)が、イソシアネートに反応する官能基を含む少なくとも1種の化合物を含む請求項1〜7のいずれか一項に記載の方法。
- 上記少なくとも一種の多官能性イソシアネート(a1)が、ジフェニルメタン4,4’−ジイソシアネート、ジフェニルメタン2,4’−ジイソシアネート、ジフェニルメタン2,2’−ジイソシアネート及びオリゴマー状ジフェニルメタンジイソシアネートから選ばれる少なくとも一種の多官能性イソシアネートからなる請求項1〜8のいずれか一項に記載の方法。
- 成分(a1)がオリゴマー状ジフェニルメタンジイソシアネートを含み、その官能価が少なくとも2.4である請求項1〜9のいずれか一項に記載の方法。
- 成分(a2)がオリゴマー状ジアミノジフェニルメタンを含み、その官能価が少なくとも2.4である請求項1〜10のいずれか一項に記載の方法。
- 上記少なくとも一種の多官能性芳香族アミンが、一般式Iの少なくとも一種の多官能性芳香族アミンを含む:
- Q2、Q4、Q2’及びQ4’が、一般式Iの化合物が、芳香族環に結合した少なくとも一個の一級アミノ基に対してα位に、他の官能基を有してもよく且つ1〜12個の炭素原子をもつ少なくとも一つの直鎖又は分岐アルキル基を持つように選ばれる請求項12に記載の方法。
- 成分(a2)が、4,4’−ジアミノジフェニルメタン、2,4’−ジアミノジフェニルメタン、2,2’−ジアミノジフェニルメタン及びオリゴマー状ジアミノジフェニルメタンの中の少なくとも一種の化合物を含む請求項1〜13のいずれか一項に記載の方法。
- 上記反応が触媒(a5)の存在下で起こる請求項1〜14のいずれか一項に記載の方法。
- 溶媒の除去が、該溶媒の臨界温度と臨界圧力未満の温度と圧力で該溶媒をガス状態に変換して起こる請求項1〜15のいずれか一項に記載の方法。
- 少なくとも一種の多官能性イソシアネート(a1)と少なくとも一種の多官能性芳香族アミン(a2)とを、有機溶媒中で、成分(a4)としての少なくとも一種の、前記溶媒に可溶である有機難燃剤の存在下で反応させ、必要なら成分(a3)としての水の存在下で、また必要なら少なくとも一種の触媒(a5)の存在下で、反応させて得られたゲルから、該有機溶媒を除いて得られた有機多孔質材料。
- 前記有機溶媒が除かれたゲルの体積平均気孔径が大きくても5μmである請求項17に記載の多孔質材料。
- 請求項17または18に記載の多孔質材料の断熱への使用。
- 請求項17または18に記載の多孔質材料の建設用途での断熱への使用。
- 成分(a4)の難燃剤が、臭素を含む化合物である請求項1に記載の方法。
- 成分(a4)の使用量が、成分(a1)〜(a4)の総質量100質量%に対して1〜15質量%である請求項1または2に記載の方法。
- 成分(a4)が、イソシアネートに反応する少なくとも2個の官能基を含む少なくとも1種の化合物を含む請求項1〜7のいずれか一項に記載の方法。
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US9321876B2 (en) | 2012-09-27 | 2016-04-26 | Basf Se | Process for producing porous materials based on isocyanate |
US10100513B2 (en) | 2012-11-05 | 2018-10-16 | Basf Se | Process for producing profiled elements |
US9676915B2 (en) | 2012-12-17 | 2017-06-13 | Basf Se | Porous branched/highly branched polyimides |
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